Lange's Handbook of Chemistry

LANGE'S HANDBOOK OF CHEMISTRY John A. Dean Professor Emeritus of Chemistry University of Tennessee, Knoxville

Fifteenth Edition

McGRAW-HILL, INC. New York St. Louis San Francisco Auckland Bogotá Caracus Lisbon London Madrid Mexico Milan Montreal New Delhi Paris San Juan São Paulo Singapore Sydney Tokyo Toronto

Copyright © 1999, 1992, 1985, 1979, 1973, 1967, 1961, 1956 by McGrawHill, Inc. All rights reserved. Copyright renewed 1972 by Norbert Adolph Lange. Copyright 1952, 1949, 1946, 1944, 1941, 1939, 1937, 1934 by McGraw-Hill, Inc. All rights reserved. Printed in the United States of America. Except as permitted under the United States Copyright Act of 1976, no part of this publication may be reproduced or distributed in any form or by any means, or stored in a data base retrieval system without the prior written permission of the publisher. 5 6 7 8 9 0 DOC/DOC 9 0 3 2 1 0 9 8 ISBN 0-07-016384-7 The sponsoring editor for this book was Robert Esposito, and the production supervisor was Clare B. Stanley. It was set in Times Roman by Progressive Information Technologies. Printed and bound by R. R. Donnelley & Sons Company.

Information contained in this work has been obtained by McGrawHill, Inc., from sources believed to be reliable. However, neither McGraw-Hill nor its authors guarantee the accuracy or completeness of any information published herein and neither McGraw-Hill nor its authors shall be responsible for any errors, omissions, or damages arising out of use of this information. This work is published with the understanding that McGraw-Hill and its authors are supplying information but are not attempting to render engineering or other professional services. If such services are required, the assistance of an appropriate profession should be sought.

Grateful acknowledgment is hereby made of an indebtedness to those who have contributed to previous editions and whose compilations continue in use in this edition. In particular, acknowledgment is made of the contribution of L. P. Buseth, who prepared the conversion tables for the thirteenth edition and who prepared the table on the U.S. Standard Sieve Series.

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ABOUT

THE EDITOR

John A. Dean assumed the editorship of Lange's Handbook of Chemistry in 1968 with the Eleventh Edition. He is currently Professor Emeritus of Chemistry at the University of Tennessee at Knoxville. The author of nine major chemistry reference books used throughout the world, John Dean's research interests, reflected in over 105 research papers and scholarly publications, include instrumental methods of analysis, flame emission and atomic absorption spectroscopy, chromatographic and solvent extraction methods, and polarography. He received his B.S., M.S., and Ph.D. in Chemistry from the University of Michigan at Ann Arbor. In 1974, he was given the Charles H. Stone Award by the Carolina-Piedmont Section of the American Chemical Society. In 1991, he was awarded the Distinguished Service Award by the Society for Applied Spectroscopy; by the same organization he was awarded Honorary Membership in 1997.

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PREFACE TO FIFTEENTH EDITION This new edition, the fifth under the aegis of the present editor, remains the one-volume source of factual information for chemists, both professionals and students — the first place in which to “look it up” on the spot. The aim is to provide sufficient data to satisfy all one’s general needs without recourse to other reference sources. A user will find this volume of value as a time-saver because of the many tables of numerical data which have been especially compiled. Descriptive properties for a basic group of approximately 4300 organic compounds are compiled in Section 1, an increase of 300 entries. All entries are listed alphabetically according to the senior prefix of the name. The data for each organic compound include (where available) name, structural formula, formula weight, Beilstein reference (or if unavailable, the entry to the Merck Index, 12th ed.), density, refractive index, melting point, boiling point, flash point, and solubility (citing numerical values if known) in water and various common organic solvents. Structural formulas either too complex or too ambiguous to be rendered as line formulas are grouped at the bottom of each facing double page on which the entries appear. Alternative names, as well as trivial names of long-standing usage, are listed in their respective alphabetical order at the bottom of each double page in the regular alphabetical sequence. Another feature that assists the user in locating a desired entry is the empirical formula index. Section 2 on General Information, Conversion Tables, and Mathematics has had the table on general conversion factors thoroughly reworked. Similarly the material on Statistics in Chemical Analysis has had its contents more than doubled. Descriptive properties for a basic group of inorganic compounds are compiled in Section 3, which has undergone a small increase in the number of entries. Many entries under the column “Solubility” supply the reader with precise quantities dissolved in a stated solvent and at a given temperature. Several portions of Section 4, Properties of Atoms, Radicals, and Bonds, have been significantly enlarged. For example, the entries under “Ionization Energy of Molecular and Radical Species” now number 740 and have an additional column with the enthalpy of formation of the ions. Likewise, the table on “Electron Affinities of the Elements, Molecules, and Radicals” now contains about 225 entries. The Table of Nuclides has material on additional radionuclides, their radiations, and the neutron capture cross sections. Revised material for Section 5 includes the material on surface tension, viscosity, dielectric constant, and dipole moment for organic compounds. In order to include more data at several temperatures, the material has been divided into two separate tables. Material on surface tension and viscosity constitute the first table with 715 entries; included is the temperature range of the liquid phase. Material on dielectric constant and dipole vii

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moment constitute another table of 1220 entries. The additional data at two or more temperatures permit interpolation for intermediate temperatures and also permit limited extrapolation of the data. The Properties of Combustible Mixtures in Air has been revised and expanded to include over 450 compounds. Flash points are to be found in Section 1. Completely revised are the tables on Thermal Conductivity for gases, liquids, and solids. Van der Waals’ constants for gases has been brought up to date and expanded to over 500 substances. Section 6, which includes Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic and Inorganic Compounds, and Heats of Melting, Vaporization, and Sublimation and Specific Heat at Various Temperatures for organic and inorganic compounds, has expanded by 11 pages, but the major additions have involved data in columns where it previously was absent. More material has also been included for critical temperature, critical pressure, and critical volume. The section on Spectroscopy has been retained but with some revisions and expansion. The section includes ultraviolet-visible spectroscopy, fluorescence, infrared and Raman spectroscopy, and X-ray spectrometry. Detection limits are listed for the elements when using flame emission, flame atomic absorption, electrothermal atomic absorption, argon induction coupled plasma, and flame atomic fluorescence. Nuclear magnetic resonance embraces tables for the nuclear properties of the elements, proton chemical shifts and coupling constants, and similar material for carbon-13, boron-11, nitrogen-15, fluorine19, silicon-19, and phosphorus-31. In Section 8, the material on solubility constants has been doubled to 550 entries. Sections on proton transfer reactions, including some at various temperatures, formation constants of metal complexes with organic and inorganic ligands, buffer solutions of all types, reference electrodes, indicators, and electrode potentials are retained with some revisions. The material on conductances has been revised and expanded, particularly in the table on limiting equivalent ionic conductances. Everything in Sections 9 and 10 on physiochemical relationships, and on polymers, rubbers, fats, oils, and waxes, respectively, has been retained. Section 11, Practical Laboratory Information, has undergone significant changes and expansion. Entries in the table on “Molecular Elevation of the Boiling Point” have been increased. McReynolds’ constants for stationary phases in gas chromatography have been reorganized and expanded. The guide to ion-exchange resins and discussion is new and embraces all types of column packings and membrane materials. Gravimetric factors have been altered to reflect the changes in atomic weights for several elements. Newly added are tables listing elements precipitated by general analytical reagents, and giving equations for the redox determination of the elements with their equivalent weights. Discussion on the topics of precipitation and complexometric titrations include primary standards and indicators for each analytical technique. A new topic of masking and demasking agents includes discussion and tables of masking agents for various elements, for anions and neutral molecules, and common demasking agents. A table has been added listing the common amino acids with their pI and pKa values and their 3-letter and 1-letter abbreviations. Lastly a 9-page table lists the threshold limit value (TLV) for gases and vapors. As stated in earlier prefaces, every effort has been made to select the most useful and reliable information and to record it with accuracy. However, the editor’s 50 years of

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involvement with textbooks and handbooks bring a realization of the opportunities for gremlins to exert their inevitable mischief. It is hoped that users of this handbook will continue to offer suggestions of material that might be included in, or even excluded from, future editions and call attention to errors. These communications should be directed to the editor. The street address will change early in 1999, as will the telephone number. However, the e-mail address should remain as “[email protected].”

Knoxville, TN

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John A. Dean

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PREFACE TO FOURTEENTH EDITION Perhaps it would be simplest to begin by stating the ways in which this new edition, the fourth under the aegis of the present editor, has not been changed. It remains the one-volume source of factual information for chemists, both professionals and students—the first place in which to “look it up” on the spot. The aim is to provide sufficient data to satisfy all one’s general needs without recourse to other reference sources. Even the worker with the facilities of a comprehensive library will find this volume of value as a time-saver because of the many tables of numerical data which have been especially compiled. The changes, however, are both numerous and significant. First of all, there is a change in the organization of the subject matter. For example, material formerly contained in the section entitled Analytical Chemistry is now grouped by operational categories: spectroscopy; electrolytes, electromotive force, and chemical equilibrium; and practical laboratory information. Polymers, rubbers, fats, oils, and waxes constitute a large independent section. Descriptive properties for a basic group of approximately 4000 organic compounds are compiled in Section 1. These follow a concise introduction to organic nomenclature, including the topic of stereochemistry. Nomenclature is consistent with the 1979 rules of the Commission on Nomenclature, International Union of Pure and Applied Chemistry (IUPAC). All entries are listed alphabetically according to the senior prefix of the name. The data for each organic compound include (where available) name, structural formula, formula weight, Beilstein reference, density, refractive index, melting point, boiling point, flash point, and solubility (citing numerical values if known) in water and various common organic solvents. Structural formulas either too complex or too ambiguous to be rendered as line formulas are grouped at the bottom of the page on which the entries appear. Alternative names, as well as trivial names of long-standing usage, are listed in their respective alphabetical order at the bottom of each page in the regular alphabetical sequence. Another feature that assists the user in locating a desired entry is the empirical formula index. Section 2 combines the former separate section on Mathematics with the material involving General Information and Conversion Tables. The fundamental physical constants reflect values recommended in 1986. Physical and chemical symbols and definitions have undergone extensive revision and expansion. Presented in 14 categories, the entries follow recommendations published in 1988 by the IUPAC. The table of abbreviations and standard letter symbols provides, in a sense, an alphabetical index to the foregoing tables. The table of conversion factors has been modified in view of recent data and inclusion of SI units; cross-entries for “archaic” or unusual entries have been curtailed. Descriptive properties for a basic group of approximately 1400 inorganic compounds are compiled in Section 3. These follow a concise, revised introduction to inorganic nomenclature that follows the recommendations of the IUPAC published in 1990. In this section are given the exact atomic (or formula) weight of the elements accompanied, when available, by the uncertainty in the final figure given in parentheses. In Section 4 the data on bond lengths and strengths have been vastly increased so as to include not only the atomic and effective ionic radii of elements and the covalent radii for atoms, but also the bond lengths between carbon and other elements and between elements other than carbon. All xi

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lengths are given in picometers (SI unit). Effective ionic radii are tabulated as a function of ion charge and coordination number. Bond dissociation energies are given in kilojoules per mole with the uncertainty of the final figure(s) given in parentheses when known. New tables include bond dipole moments, group dipole moments, work functions of the elements, and relative abundances of the naturally occurring elements. The table of nuclides has been shortened and includes only the more commonly encountered nuclides; tabulations list half-life, natural abundance, cross-section to thermal neutrons, and radiation emitted upon disintegration. Entries have been updated. Revised material in Section 5 includes an extensive tabulation of binary and ternary azeotropes comprising approximately 850 entries. Over 975 compounds have values listed for viscosity, dielectric constant, dipole moment, and surface tension. Whenever possible, data for viscosity and dielectric constant are provided at two temperatures to permit interpolation for intermediate temperatures and also to permit limited extrapolation of the data. The dipole moments are often listed for different physical states. Values for surface tension can be calculated over a range of temperatures from two constants that can be fitted into a linear equation. Also extensively revised and expanded are the properties of combustible mixtures in air. A table of triple points has been added. The tables in Section 6 contain values of the enthalpy and Gibbs energy of formation, entropy, and heat capacity at five temperatures for approximately 2000 organic compounds and 1500 inorganic compounds, many in more than one physical state. Separate tabulations have enthalpies of melting, vaporization, transition, and sublimation for organic and inorganic compounds. All values are given in SI units (joule) and have been extracted from the latest sources such as JANAF Thermochemical Tables, 3d ed. (1986); Thermochemical Data of Organic Compounds, 2d ed. (1986); and Enthalpies of Vaporization of Organic Compounds, published under the auspices of the IUPAC (1985). Also updated is the material on critical properties of elements and compounds. The section on Spectroscopy has been expanded to include ultraviolet-visible spectroscopy, fluorescence, Raman spectroscopy, and mass spectroscopy. Retained sections have been thoroughly revised: in particular, the tables on electronic emission and atomic absorption spectroscopy, nuclear magnetic resonance, and infrared spectroscopy. Detection limits are listed for the elements when using flame emission, flame atomic absorption, electrothermal atomic absorption, argon ICP, and flame atomic fluorescence. Nuclear magnetic resonance embraces tables for the nuclear properties of the elements, proton chemical shifts and coupling constants, and similar material for carbon-13, boron-11, nitrogen-15, fluorine-19, silicon-29, and phosphorus-31. Section 8 now combines all the material on electrolytes, electromotive force, and chemical equilibrium, some of which had formerly been included in the old “Analytical Chemistry” section of earlier editions. Material on the half-wave potentials of inorganic and organic materials has been thoroughly revised. The tabulation of the potentials of the elements and their compounds reflects recent IUPAC (1985) recommendations. An extensive new Section 10 is devoted to polymers, rubbers, fats, oils, and waxes. A discussion of polymers and rubbers is followed by the formulas and key properties of plastic materials. For each member and type of the plastic families there is a tabulation of their physical, electrical, mechanical, and thermal properties and characteristics. A similar treatment is accorded the various types of rubber materials. Chemical resistance and gas permeability constants are also given for rubbers and plastics. The section concludes with various constants of fats, oils, and waxes. The practical laboratory information contained in Section 11 has been gathered from many of the previous sections of earlier editions. This material has been supplemented with new material under separation methods, gravimetric and volumetric analysis, and laboratory solutions. Significant new tables under separation methods include: properties of solvents for chromatography, solvents having the same refractive index and the same density, McReynolds’ constants for stationary phases in gas chromatography, characteristics of selected supercritical fluids, and typical performances in HPLC for various operating conditions. Under gravimetric and volumetric analysis, gravimetric factors, equations and equivalents for volumetric analysis, and titrimetric factors have been retained

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along with the formation constants of EDTA metal complexes. In this age of awareness of chemical dangers, tables have been added for some common reactive and incompatible chemicals, chemicals recommended for refrigerated storage, and chemicals which polymerize or decompose on extended storage at low temperature. Updated is the information about the U.S. Standard Sieve Series. Thermometry data have been revised to bring them into agreement with the new International Temperature Scale– 1990, and data for type N thermocouples are included. Every effort has been made to select the most useful and most reliable information and to record it with accuracy. However, the editor’s many years of involvement with handbooks bring a realization of the opportunities for gremlins to exert their inevitable mischief. It is hoped that users of this handbook will offer suggestions of material that might be included in, or even excluded from, future editions and call attention to errors. These communications should be directed to the editor at his home address (or by telephone).

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John A. Dean

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PREFACE TO FIRST EDITION This book is the result of a number of years’ experience in the compiling and editing of data useful to chemists. In it an effort has been made to select material to meet the needs of chemists who cannot command the unlimited time available to the research specialist, or who lack the facilities of a large technical library which so often is not conveniently located at many manufacturing centers. If the information contained herein serves this purpose, the compiler will feel that he has accomplished a worthy task. Even the worker with the facilities of a comprehensive library may find this volume of value as a time-saver because of the many tables of numerical data which have been especially computed for this purpose. Every effort has been made to select the most reliable information and to record it with accuracy. Many years of occupation with this type of work bring a realization of the opportunities for the occurrence of errors, and while every endeavor has been made to prevent them, yet it would be remarkable if the attempts towards this end had always been successful. In this connection it is desired to express appreciation to those who in the past have called attention to errors, and it will be appreciated if this be done again with the present compilation for the publishers have given their assurance that no expense will be spared in making the necessary changes in subsequent printings. It has been aimed to produce a compilation complete within the limits set by the economy of available space. One difficulty always at hand to the compiler of such a book is that he must decide what data are to be excluded in order to keep the volume from becoming unwieldy because of its size. He can hardly be expected to have an expert’s knowledge of all branches of the science nor the intuition necessary to decide in all cases which particular value to record, especially when many differing values are given in the literature for the same constant. If the expert in a particular field will judge the usefulness of this book by the data which it supplies to him from fields other than his specialty and not by the lack of highly specialized information in which only he and his co-workers are interested (and with which he is familiar and for which he would never have occasion to consult this compilation), then an estimate of its value to him will be apparent. However, if such specialists will call attention to missing data with which they are familiar and which they believe others less specialized will also need, then works of this type can be improved in succeeding editions. Many of the gaps in this volume are caused by the lack of such information in the literature. It is hoped that to one of the most important classes of workers in chemistry, namely the teachers, the book will be of value not only as an aid in answering the most varied questions with which they are confronted by interested students, but also as an inspiration through what it suggests by the gaps and inconsistencies, challenging as they do the incentive to engage in the creative and experimental work necessary to supply the missing information. While the principal value of the book is for the professional chemist or student of chemistry, it should also be of value to many people not especially educated as chemists. Workers in the natural sciences— physicists, mineralogists, biologists, pharmacists, engineers, patent attorneys, and librarians— are often called upon to solve problems dealing with the properties of chemical products or materials of construction. For such needs this compilation supplies helpful information and will serve not only as an economical substitute for the costly accumulation of a large library of monographs on specialized subjects, but also as a means of conserving the time required to search for xv

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information so widely scattered throughout the literature. For this reason especial care has been taken in compiling a comprehensive index and in furnishing cross references with many of the tables. It is hoped that this book will be of the same usefulness to the worker in science as is the dictionary to the worker in literature, and that its resting place will be on the desk rather than on the bookshelf. Cleveland, Ohio May 2, 1934

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N. A. Lange

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For the detailed contents of any section, consult the title page of that section. See also the alpha. betical index in the back of this handbook.

Preface to Fifteenth

Edition

Preface to Fourteenth Preface to First Edition Acknowledgments

Section Section Section Section Section Section Section Section

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Edition xv xvii

1. 2. 3. 4. 5. 6. 7. 8.

Organic Compounds General Information, Conversion Tables, and Mathematics Inorganic Compounds Properties of Atoms, Radicals, and Bonds Physical Properties Thermodynamic Properties Spectroscopy Electrolytes, Electromotive Force, and Chemical Equilibrium Section 9. Physicochemical Relationships Section 10. Polymers, Rubbers, Fats, Oils, and Waxes Section 11. Practical Laboratory Information

Index follows

Section

11

1.1 2.1 3.1 4.1 5.1 6.1 7.1

8.1 9.1 10.1 11.1

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SECTION 1

ORGANIC COMPOUNDS 1.1 NOMENCLATURE OF ORGANIC COMPOUNDS 1.1.1 Nonfunctional Compounds Table 1.1 Names of Straight-Chain Alkanes Table 1.2 Fused Polycyclic Hydrocarbons Table 1.3 Specialist Nomenclature for Heterocyclic Systems Table 1.4 Suffixes for Specialist Nomenclature of Heterocyclic Systems Table 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names Table 1.6 Trivial Names for Heterocyclic Systems That Are Not Recommended for Use in Fusion Names 1.1.2 Functional Compounds Table 1.7 Characteristic Groups for Substitutive Nomenclature Table 1.8 Characteristic Groups Cited Only as Prefixes in Substitutive Nomenclature Table 1.9 Functional Class Names Used in Radicofunctional Nomenclature 1.1.3 Specific Functional Groups Table 1.10 Retained Trivial Names of Alcohols and Phenols with Structures Table 1.11 Names of Some Carboxylic Acids Table 1.12 Parent Structures of Phosphorus-Containing Compounds 1.1.4 Stereochemistry 1.1.5 Chemical Abstracts Indexing System Table 1.13 Names and Formulas of Organic Radicals 1.2 PHYSICAL PROPERTIES OF PURE SUBSTANCES Table 1.14 Empirical Formula Index of Organic Compounds Table 1.15 Physical Constants of Organic Compounds

1.1

1.1 1.1 1.2 1.8 1.11 1.12 1.13 1.16 1.17 1.18 1.19 1.22 1.23 1.24 1.30 1.36 1.39 1.49 1.51 1.58 1.58 1.74

NOMENCLATURE OF ORGANIC COMPOUNDS

The following synopsis of rules for naming organic compounds and the examples given in explanation are not intended to cover all the possible cases. For a more comprehensive and detailed description, see J. Rigaudy and S. P. Klesney, Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, Pergamon Press, Oxford, 1979. This publication contains the recommendations of the Commission on Nomenclature of Organic Chemistry and was prepared under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).

1.1.1

Nonfunctional Compounds

1.1.1.1 Alkanes. The saturated open-chain (acyclic) hydrocarbons (CnH2n⫹2) have names ending in -ane. The first four members have the trivial names methane (CH4), ethane (CH3CH3 or C2H6), propane (C3H8), and butane (C4H10). For the remainder of the alkanes, the first portion of the name 1.1

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is derived from the Greek prefix (see Table 2.4) that cites the number of carbons in the alkane followed by -ane with elision of the terminal -a from the prefix, as shown in Table 1.1.

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TABLE 1.1 Names of Straight-Chain Alkanes n*

Name

n*

Name

n*

Name

1 2 3 4 5 6 7 8 9 10

Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane† Decane

11 12 13 14 15 16 17 18 19 20

Undecane‡ Dodecane Tridecane Tetradecane Pentadecane Hexadecane Heptadecane Octadecane Nonadecane Icosane§

21 22 23

Henicosane Docosane Tricosane

30 31 32

Triacontane Hentriacontane Dotriacontane

40 50

Tetracontane Pentacontane

n*

Name

60 70 80 90 100 110 120 121

Hexacontane Heptacontane Octacontane Nonacontane Hectane Decahectane Icosahectane Henicosahectane

* n ⫽ total number of carbon atoms. † Formerly called enneane. ‡ Formerly called hendecane. § Formerly called eicosane.

For branching compounds, the parent structure is the longest continuous chain present in the compound. Consider the compound to have been derived from this structure by replacement of hydrogen by various alkyl groups. Arabic number prefixes indicate the carbon to which the alkyl group is attached. Start numbering at whichever end of the parent structure that results in the lowestnumbered locants. The arabic prefixes are listed in numerical sequence, separated from each other by commas and from the remainder of the name by a hyphen. If the same alkyl group occurs more than once as a side chain, this is indicated by the prefixes di-, tri-, tetra-, etc. Side chains are cited in alphabetical order (before insertion of any multiplying prefix). The name of a complex radical (side chain) is considered to begin with the first letter of its complete name. Where names of complex radicals are composed of identical words, priority for citation is given to that radical which contains the lowest-numbered locant at the first cited point of difference in the radical. If two or more side chains are in equivalent positions, the one to be assigned the lowest-numbered locant is that cited first in the name. The complete expression for the side chain may be enclosed in parentheses for clarity or the carbon atoms in side chains may be indicated by primed locants. If hydrocarbon chains of equal length are competing for selection as the parent, the choice goes in descending order to (1) the chain that has the greatest number of side chains, (2) the chain whose side chains have the lowest-numbered locants, (3) the chain having the greatest number of carbon atoms in the smaller side chains, or (4) the chain having the least-branched side chains. These trivial names may be used for the unsubstituted hydrocarbon only: Isobutane Isopentane

(CH3)2CHCH3 (CH3)2CHCH2CH3

Neopentane Isohexane

(CH3)4C (CH3)2CHCH2CH2CH3

Univalent radicals derived from saturated unbranched alkanes by removal of hydrogen from a terminal carbon atom are named by adding -yl in place of -ane to the stem name. Thus the alkane

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ethane becomes the radical ethyl. These exceptions are permitted for unsubstituted radicals only: Isopropyl Isobutyl

(CH3)2CH9

Isopentyl

(CH3)2CHCH2 9

Neopentyl

sec-Butyl

CH3CH2CH(CH3) 9

tert-Pentyl

tert-Butyl

(CH3)3C9

Isohexyl

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(CH3)2CHCH2CH2 9 (CH3)3CCH2 9 CH3CH2C(CH3)2 9 (CH3)2CHCH2CH2CH2 9

Note the usage of the prefixes iso-, neo-, sec-, and tert-, and note when italics are employed. Italicized prefixes are never involved in alphabetization, except among themselves; thus sec-butyl would precede isobutyl, isohexyl would precede isopropyl, and sec-butyl would precede tert-butyl. Examples of alkane nomenclature are 2-Methylbutane (or the trivial name, isopentane)

3-Methylpentane (not 2-ethylbutane)

5-Ethyl-2,2-dimethyloctane (note cited order)

3-Ethyl-6-methyloctane (note locants reversed)

4,4-Bis(1,1-dimethylethyl)-2-methyloctane 4,4-Bis-1⬘,1⬘-dimethylethyl-2-methyloctane 4,4-Bis(tert-butyl)-2-methyloctane Bivalent radicals derived from saturated unbranched alkanes by removal of two hydrogen atoms are named as follows: (1) If both free bonds are on the same carbon atom, the ending -ane of the hydrocarbon is replaced with -ylidene. However, for the first member of the alkanes it is methylene

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rather than methylidene. Isopropylidene, sec-butylidene, and neopentylidene may be used for the unsubstituted group only. (2) If the two free bonds are on different carbon atoms, the straight-chain group terminating in these two carbon atoms is named by citing the number of methylene groups comprising the chain. Other carbon groups are named as substituents. Ethylene is used rather than dimethylene for the first member of the series, and propylene is retained for CH3 9 CH 9 CH2 9 (but trimethylene is 9 CH2 9 CH2 9CH2 9). Trivalent groups derived by the removal of three hydrogen atoms from the same carbon are named by replacing the ending -ane of the parent hydrocarbon with -ylidyne.

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1.1.1.2 Alkenes and Alkynes. Each name of the corresponding saturated hydrocarbon is converted to the corresponding alkene by changing the ending -ane to -ene. For alkynes the ending is -yne. With more than one double (or triple) bond, the endings are -adiene, -atriene, etc. (or -adiyne, -atriyne, etc.). The position of the double (or triple) bond in the parent chain is indicated by a locant obtained by numbering from the end of the chain nearest the double (or triple) bond; thus CH3CH2CH" CH2 is 1-butene and CH3C#CCH3 is 2-butyne. For multiple unsaturated bonds, the chain is so numbered as to give the lowest possible locants to the unsaturated bonds. When there is a choice in numbering, the double bonds are given the lowest locants, and the alkene is cited before the alkyne where both occur in the name. Examples: CH3CH2CH2CH2CH"CH9CH" CH2 CH2 "CHC#CCH"CH2 CH3CH"CHCH2C# CH CH# CCH2CH"CH2

1,3-Octadiene

1,5-Hexadiene-3-yne 4-Hexen-1-yne 1-Penten-4-yne

Unsaturated branched acyclic hydrocarbons are named as derivatives of the chain that contains the maximum number of double and/or triple bonds. When a choice exists, priority goes in sequence to (1) the chain with the greatest number of carbon atoms and (2) the chain containing the maximum number of double bonds. These nonsystematic names are retained: Ethylene Allene Acetylene

CH2 "CH2 CH2 "C"CH2 HC#CH

An example of nomenclature for alkenes and alkynes is

4-Propyl-3-vinyl-1,3-hexadien-5-yne

Univalent radicals have the endings -enyl, -ynyl, -dienyl, -diynyl, etc. When necessary, the positions of the double and triple bonds are indicated by locants, with the carbon atom with the free valence numbered as 1. Examples: CH2 "CH9CH2 9 CH3 9C#C9

2-Propenyl 1-Propynyl

CH3 9C#C9 CH2CH "CH2 9 These names are retained:

1-Hexen-4-ynyl

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Vinyl (for ethenyl)

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CH2 "CH9

Allyl (for 2-propenyl)

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CH2 "CH9 CH2 9

Isopropenyl (for 1-methylvinyl but for unsubstituted radical only)

CH2 "C(CH3) 9

Should there be a choice for the fundamental straight chain of a radical, that chain is selected which contains (1) the maximum number of double and triple bonds, (2) the largest number of carbon atoms, and (3) the largest number of double bonds. These are in descending priority. Bivalent radicals derived from unbranched alkenes, alkadienes, and alkynes by removing a hydrogen atom from each of the terminal carbon atoms are named by replacing the endings -ene, -diene, and -yne by -enylene, -dienylene, and -ynylene, respectively. Positions of double and triple bonds are indicated by numbers when necessary. The name vinylene instead of ethenylene is retained for 9CH "CH9 . 1.1.1.3 Monocyclic Aliphatic Hydrocarbons. Monocyclic aliphatic hydrocarbons (with no side chains) are named by prefixing cyclo- to the name of the corresponding open-chain hydrocarbon having the same number of carbon atoms as the ring. Radicals are formed as with the alkanes, alkenes, and alkynes. Examples: Cyclohexane

Cyclohexyl- (for the radical)

Cyclohexene

1-Cyclohexenyl- (for the radical with the free valence at carbon 1)

1,3-Cyclohexandiene

Cyclohexadienyl- (the unsaturated carbons are given numbers as low as possible, numbering from the carbon atom with the free valence given the number 1)

For convenience, aliphatic rings are often represented by simple geometric figures: a triangle for cyclopropane, a square for cyclobutane, a pentagon for cyclopentane, a hexagon (as illustrated) for cyclohexane, etc. It is understood that two hydrogen atoms are located at each corner of the figure unless some other group is indicated for one or both. 1.1.1.4 Monocyclic Aromatic Compounds. Except for six retained names, all monocyclic substituted aromatic hydrocarbons are named systematically as derivatives of benzene. Moreover, if the substituent introduced into a compound with a retained trivial name is identical with one already present in that compound, the compound is named as a derivative of benzene. These names are retained:

Cumene

Cymene (all three forms; para- shown)

Mesitylene

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Styrene

Toluene

Xylene (all three forms; meta- shown)

The position of substituents is indicated by numbers, with the lowest locant possible given to substituents. When a name is based on a recognized trivial name, priority for lowest-numbered locants is given to substituents implied by the trivial name. When only two substituents are present on a benzene ring, their position may be indicated by o- (ortho-), m- (meta-), and p- (para-) (and alphabetized in the order given) used in place of 1,2-, 1,3-, and 1,4-, respectively. Radicals derived from monocyclic substituted aromatic hydrocarbons and having the free valence at a ring atom (numbered 1) are named phenyl (for benzene as parent, since benzyl is used for the radical C6H5CH2 9 ), cumenyl, mesityl, tolyl, and xylyl. All other radicals are named as substituted phenyl radicals. For radicals having a single free valence in the side chain, these trivial names are retained: Benzyl

C6H5CH2 9

Benzhydryl (alternative to diphenylmethyl) (C6H5)2CH9 Cinnamyl

Phenethyl

C6H5CH2CH2 9

Styryl

C6H5CH"CH9

Trityl

(C6H5)3C 9

C6H5CH" CH9CH2 9

Otherwise, radicals having the free valence(s) in the side chain are named in accordance with the rules for alkanes, alkenes, or alkynes. The name phenylene (o-, m-, or p-) is retained for the radical 9C6H4 9 . Bivalent radicals formed from substituted benzene derivatives and having the free valences at ring atoms are named as substituted phenylene radicals, with the carbon atoms having the free valences being numbered 1,2-, 1,3-, or 1,4-, as appropriate. Radicals having three or more free valences are named by adding the suffixes -triyl, -tetrayl, etc. to the systematic name of the corresponding hydrocarbon. 1.1.1.5 Fused Polycyclic Hydrocarbons. The names of polycyclic hydrocarbons containing the maximum number of conjugated double bonds end in -ene. Here the ending does not denote one double bond. Names of hydrocarbons containing five or more fixed benzene rings in a linear arrangement are formed from a numerical prefix (see Table 2.4) followed by -acene. A partial list of the names of polycyclic hydrocarbons is given in Table 1.2. Many names are trivial. Numbering of each ring system is fixed, as shown in Table 1.2, but it follows a systematic pattern. The individual rings of each system are oriented so that the greatest number of rings are (1) in a horizontal row and (2) the maximum number of rings are above and to the right (upper-right quadrant) of the horizontal row. When two orientations meet these requirements, the one is chosen that has the fewest rings in the lower-left quadrant. Numbering proceeds in a clockwise direction, commencing with the carbon atom not engaged in ring fusion that lies in the most counterclockwise position of the uppermost ring (upper-right quadrant); omit atoms common to two or more rings. Atoms common to two or more rings are designated by adding lowercase roman letters to the number of the position immediately preceding. Interior atoms follow the highest number, taking a clockwise

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sequence wherever there is a choice. Anthracene and phenanthrene are two exceptions to the rule on numbering. Two examples of numbering follow:

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When a ring system with the maximum number of conjugated double bonds can exist in two or more forms differing only in the position of an “extra” hydrogen atom, the name can be made specific by indicating the position of the extra hydrogen(s). The compound name is modified with a locant followed by an italic capital H for each of these hydrogen atoms. Carbon atoms that carry an indicated hydrogen atom are numbered as low as possible. For example, 1H-indene is illustrated in Table 1.2; 2H-indene would be

Names of polycyclic hydrocarbons with less than the maximum number of noncumulative double bonds are formed from a prefix dihydro-, tetrahydro-, etc., followed by the name of the corresponding unreduced hydrocarbon. The prefix perhydro- signifies full hydrogenation. For example, 1,2-dihydronaphthalene is

Examples of retained names and their structures are as follows:

Indan

Acenaphthene

Aceanthrene

Acephenanthrene Polycyclic compounds in which two rings have two atoms in common or in which one ring contains two atoms in common with each of two or more rings of a contiguous series of rings and which contain at least two rings of five or more members with the maximum number of noncumu-

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TABLE 1.2 Fused Polycyclic Hydrocarbons Listed in order of increasing priority for selection as parent compound. 1. Pentalene

9. Acenaphthylene

2. Indene 10. Fluorene

3. Naphthalene

11. Phenalene

4. Azulene 12. Phenanthrene*

5. Heptalene 13. Anthracene*

14. Fluoranthene 6. Biphenylene

7. asym-Indacene

15. Acephenanthrylene

8. sym-Indacene

16. Aceanthrylene

* Asterisk after a compound denotes exception to systematic numbering.

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TABLE 1.2 Fused Polycyclic Hydrocarbons (Continued) 17. Triphenylene

19. Chrysene

18. Pyrene

20. Naphthacene

lative double bonds and which have no accepted trivial name (Table 1.2) are named by prefixing to the name of the parent ring or ring system designations of the other components. The parent name should contain as many rings as possible (provided it has a trivial name) and should occur as far as possible from the beginning of the list in Table 1.2. Furthermore, the attached component(s) should be as simple as possible. For example, one writes dibenzophenanthrene and not naphthophenanthrene because the attached component benzo- is simpler than napththo-. Prefixes designating attached components are formed by changing the ending -ene into -eno-; for example, indeno- from indene. Multiple prefixes are arranged in alphabetical order. Several abbreviated prefixes are recognized; the parent is given in parentheses: Acenaphtho-

(acenaphthylene)

Naphtho-

Anthra-

(anthracene)

Perylo-

Benzo-

(benzene)

Phenanthro-

(naphthalene) (perylene) (phenanthrene)

For monocyclic prefixes other than benzo-, the following names are recognized, each to represent the form with the maximum number of noncumulative double bonds: cyclopenta-, cyclohepta-, cycloocta-, etc. Isomers are distinguished by lettering the peripheral sides of the parent beginning with a for the side 1,2, and so on, lettering every side around the periphery. If necessary for clarity, the numbers of the attached position (1,2, for example) of the substituent ring are also denoted. The prefixes are cited in alphabetical order. The numbers and letters are enclosed in square brackets and placed immediately after the designation of the attached component. Examples are

Benz[␣]anthracene

Anthra[2,1-␣]naphthacene

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1.1.1.6 Bridged Hydrocarbons. Saturated alicyclic hydrocarbon systems consisting of two rings that have two or more atoms in common take the name of the open-chain hydrocarbon containing the same total number of carbon atoms and are preceded by the prefix bicyclo-. The system is numbered commencing with one of the bridgeheads, numbering proceeding by the longest possible path to the second bridgehead. Numbering is then continued from this atom by the longer remaining unnumbered path back to the first bridgehead and is completed by the shortest path from the atom next to the first bridgehead. When a choice in numbering exists, unsaturation is given the lowest numbers. The number of carbon atoms in each of the bridges connecting the bridgeheads is indicated in brackets in descending order. Examples are

Bicyclo[3.2.1]octane

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Bicyclo[5.2.0]nonane

1.1.1.7 Hydrocarbon Ring Assemblies. Assemblies are two or more cyclic systems, either single rings or fused systems, that are joined directly to each other by double or single bonds. For identical systems naming may proceed (1) by placing the prefix bi- before the name of the corresponding radical or (2), for systems joined through a single bond, by placing the prefix bi- before the name of the corresponding hydrocarbon. In each case, the numbering of the assembly is that of the corresponding radical or hydrocarbon, one system being assigned unprimed numbers and the other primed numbers. The points of attachment are indicated by placing the appropriate locants before the name; an unprimed number is considered lower than the same number primed. The name biphenyl is used for the assembly consisting of two benzene rings. Examples are

1,1⬘-Bicyclopropyl or 1,1⬘-bicyclopropane

2-Ethyl-2⬘-propylbiphenyl

For nonidentical ring systems, one ring system is selected as the parent and the other systems are considered as substituents and are arranged in alphabetical order. The parent ring system is assigned unprimed numbers. The parent is chosen by considering the following characteristics in turn until a decision is reached: (1) the system containing the larger number of rings, (2) the system containing the larger ring, (3) the system in the lowest state of hydrogenation, and (4) the highestorder number of ring systems set forth in Table 1.2. Examples are given, with the deciding priority given in parentheses preceding the name: (1) 2-Phenylnaphthalene (2) and (4) 2-(2⬘-Naphthyl)azulene (3) Cyclohexylbenzene 1.1.1.8 Radicals from Ring Systems. Univalent substituent groups derived from polycyclic hydrocarbons are named by changing the final e of the hydrocarbon name to -yl. The carbon atoms having free valences are given locants as low as possible consistent with the fixed numbering of the

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hydrocarbon. Exceptions are naphthyl (instead of naphthalenyl), anthryl (for anthracenyl), and phenanthryl (for phenanthrenyl). However, these abbreviated forms are used only for the simple ring systems. Substituting groups derived from fused derivatives of these ring systems are named systematically. Substituting groups having two or more free bonds are named as described in Monocyclic Aliphatic Hydrocarbons on p. 1.5.

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1.1.1.9 Cyclic Hydrocarbons with Side Chains. Hydrocarbons composed of cyclic and aliphatic chains are named in a manner that is the simplest permissible or the most appropriate for the chemical intent. Hydrocarbons containing several chains attached to one cyclic nucleus are generally named as derivatives of the cyclic compound, and compounds containing several side chains and/or cyclic radicals attached to one chain are named as derivatives of the acyclic compound. Examples are 2-Ethyl-1-methylnaphthalene

Diphenylmethane

1,5-Diphenylpentane

2,3-Dimethyl-1-phenyl-1-hexene

Recognized trivial names for composite radicals are used if they lead to simplifications in naming. Examples are 1-Benzylnaphthalene

1,2,4-Tris(3-p-tolylpropyl)benzene

Fulvene, for methylenecyclopentadiene, and stilbene, for 1,2-diphenylethylene, are trivial names that are retained. 1.1.1.10 Heterocyclic Systems. Heterocyclic compounds can be named by relating them to the corresponding carbocyclic ring systems by using replacement nomenclature. Heteroatoms are denoted by prefixes ending in a, as shown in Table 1.3. If two or more replacement prefixes are required in a single name, they are cited in the order of their listing in the table. The lowest possible numbers consistent with the numbering of the corresponding carbocyclic system are assigned to the heteroatoms and then to carbon atoms bearing double or triple bonds. Locants are cited immediately preceding the prefixes or suffixes to which they refer. Multiplicity of the same heteroatom is indicated by the appropriate prefix in the series: di-, tri-, tetra-, penta-, hexa-, etc.

TABLE 1.3 Specialist Nomenclature for Heterocyclic Systems Heterocyclic atoms are listed in decreasing order of priority. Element

Valence

Prefix

Element

Valence

Prefix

Oxygen Sulfur Selenium Tellurium Nitrogen Phosphorus Arsenic

2 2 2 2 3 3 3

OxaThiaSelenaTelluraAzaPhospha-* Arsa-*

Antimony Bismuth Silicon Germanium Tin Lead Boron Mercury

3 3 4 4 4 4 3 2

Stiba-* BismaSilaGermaStannaPlumbaBoraMercura-

* When immediately followed by -in or -ine, phospha- should be replaced by phosphor-, arsa- by arsen-, and stibaby antimon-. The saturated six-membered rings corresponding to phosphorin and arsenin are named phosphorinane and arsenane. A further exception is the replacement of borin by borinane.

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TABLE 1.4 Suffixes for Specialist Nomenclature of Heterocyclic Systems Rings containing nitrogen

Rings containing no nitrogen

Number of ring members

Unsaturation*

Saturation

Unsaturation*

Saturation

3 4 5 6 7 8 9 10

-irine -ete -ole -ine† -epine -ocine -onine -ecine

-iridine -etidine -olidine ‡ ‡ ‡ ‡ ‡

-irene -ete -ole -in -epin -ocin -onin -ecin

-irane -etane -olane -ane§ -epane -ocane -onane -ecane

* Unsaturation corresponding to the maximum number of noncumulative double bonds. Heteroatoms have the normal valences given in Table 1.3. † For phosphorus, arsenic, antimony, and boron, see the special provisions in Table 1.3. ‡ Expressed by prefixing perhydro- to the name of the corresponding unsaturated compound. § Not applicable to silicon, germanium, tin, and lead; perhydro- is prefixed to the name of the corresponding unsaturated compound.

If the corresponding carbocyclic system is partially or completely hydrogenated, the additional hydrogen is cited using the appropriate H- or hydro- prefixes. A trivial name from Tables 1.5 and 1.6, if available, along with the state of hydrogenation may be used. In the specialist nomenclature for heterocyclic systems, the prefix or prefixes from Table 1.3 are combined with the appropriate stem from Table 1.4, eliding an a where necessary. Examples of acceptable usage, including (1) replacement and (2) specialist nomenclature, are

(1) 1-Oxa-4-azacyclohexane (2) 1,4-Oxazoline Morpholine

(1) 1,3-Diazacyclohex-5-ene (2) 1,2,3,4-Tetrahydro-1,3-diazine

(1) Thiacyclopropane (2) Thiirane Ethylene sulfide

Radicals derived from heterocyclic compounds by removal of hydrogen from a ring are named by adding -yl to the names of the parent compounds (with elision of the final e, if present). These exceptions are retained: Furyl (from furan)

Furfuryl (for 2-furylmethyl)

Pyridyl (from pyridine)

Furfurylidene (for 2-furylmethylene)

Piperidyl (from piperidine)

Thienyl (from thiophene)

Quinolyl (from quinoline)

Thenylidyne (for thienylmethylidyne)

Isoquinolyl

Furfurylidyne (for 2-furylmethylidyne)

Thenylidene (for thienylmethylene)

Thenyl (for thienylmethyl)

Also, piperidino- and morpholino- are preferred to 1-piperidyl- and 4-morpholinyl-, respectively.

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TABLE 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names Listed in order of increasing priority as senior ring system. Structure

Parent name Thiophene

Radical name Thienyl

Thianthrene

Thianthrenyl

Furan

Furyl

Pyran (2H-shown)

Isobenzofuran

Chromene (2H-shown)

Xanthene*

Phenoxathiin

Structure

Parent name

Radical name

2H-Pyrrole

2H-Pyrrolyl

Pyrrole

Pyrrolyl

Imidazole

Imidazolyl

Pyrazole

Pyrazolyl

Isothiazole

Isothiazolyl

Isoxazole

Isoxazolyl

Pyridine

Pyridyl

Pyrazine

Pyrazinyl

Pyrimidine

Pyrimidinyl

Pyridazine

Pyridazinyl

Pyranyl

Isobenzofuranyl

Chromenyl

Xanthenyl

Phenoxathiinyl

* Asterisk after a compound denotes exception to systematic numbering.

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TABLE 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names (Continued) Structure

Parent name

Radical name

Structure

Parent name

Radical name

Indolizine

Indolizinyl

Phthalazine

Phthalazinyl

Isoindole

Isoindolyl

Naphthyridine (1,8-shown)

Naphthyridinyl

3H-Indole

3H-Indolyl Quinoxaline

Quinoxalinyl

Quinazoline

Quinazolinyl

Cinnoline

Cinnolinyl

Pteridine

Pteridinyl

4␣HCarbazole*

4␣HCarbazolyl

Carbazole*

Carbazolyl

Indole

1H-Indazole

Purine*

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Indolyl

1H-Indazolyl

Purinyl

4H-Quinolizine

4H-Quinolizinyl

Isoquinoline

Isoquinolyl

Quinolone

Quinolyl

* Asterisk after a compound denotes exception to systematic numbering.

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TABLE 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names (Continued) Structure

Parent name

Radical name

Structure

Parent name

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Radical name

␤-Carboline

␤-Carbolinyl

Phenazine

Phenazinyl

Phenanthridine

Phenanthridinyl

Phenarsazine

Phenarsazinyl

Acridine*

Acridinyl

Perimidine

Perimidinyl

Phenothiazine

Phenothiazinyl

Furazan

Furazanyl

Phenoxazine

Phenoxazinyl

Phenanthroline (1,10-shown)

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Phenanthrolinyl

* Asterisk after a compound denotes exception to systematic numbering.

If there is a choice among heterocyclic systems, the parent compound is decided in the following order of preference: 1. A nitrogen-containing component 2. A component containing a heteroatom, in the absence of nitrogen, as high as possible in Table 1.3 3. A component containing the greater number of rings

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TABLE 1.6 Trivial Names of Heterocyclic Systems That Are Not Recommended for Use in Fusion Names

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Listed in order of increasing priority. Structure

Parent name

Radical name

Isochroman

Isochromanyl

Chroman

Chromanyl

Pyrrolidine

Pyrrolinyl

Pyrroline (2-shown*)

Pyrrolinyl

Imidazolidine

Imidazoline (2-shown*)

Pyrazolidine

Structure

Parent name

Radical name

Pyrazoline (3-shown*)

Pyrazolinyl

Piperidine

Piperidyl†

Piperazine

Piperazinyl

Indoline

Indolinyl

Isoindoline

Isoindolinyl

Quinuclidine

Quinuclidinyl

Morpholine

Morpholinyl‡

Imidazolidinyl

Imidazolinyl

Pyrazolidinyl

* Denotes position of double bond. † For 1-piperidyl, use piperidino. ‡ For 4-morpholinyl, use morpholino.

4. A component containing the largest possible individual ring 5. A component containing the greatest number of heteroatoms of any kind 6. A component containing the greatest variety of heteroatoms 7. A component containing the greatest number of heteroatoms first listed in Table 1.3

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If there is a choice between components of the same size containing the same number and kind of heteroatoms, choose as the base component that one with the lower numbers for the heteroatoms before fusion. When a fusion position is occupied by a heteroatom, the names of the component rings to be fused are selected to contain the heteroatom.

1.1.2

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Functional Compounds

There are several types of nomenclature systems that are recognized. Which type to use is sometimes obvious from the nature of the compound. Substitutive nomenclature, in general, is preferred because of its broad applicability, but radicofunctional, additive, and replacement nomenclature systems are convenient in certain situations. 1.1.2.1 Substitutive Nomenclature. The first step is to determine the kind of characteristic (functional) group for use as the principal group of the parent compound. A characteristic group is a recognized combination of atoms that confers characteristic chemical properties on the molecule in which it occurs. Carbon-to-carbon unsaturation and heteroatoms in rings are considered nonfunctional for nomenclature purposes. Substitution means the replacement of one or more hydrogen atoms in a given compound by some other kind of atom or group of atoms, functional or nonfunctional. In substitutive nomenclature, each substituent is cited as either a prefix or a suffix to the name of the parent (or substituting radical) to which it is attached; the latter is denoted the parent compound (or parent group if a radical). In Table 1.7 are listed the general classes of compounds in descending order of preference for citation as suffixes, that is, as the parent or characteristic compound. When oxygen is replaced by sulfur, selenium, or tellurium, the priority for these elements is in the descending order listed. The higher valence states of each element are listed before considering the successive lower valence states. Derivative groups have priority for citation as principal group after the respective parents of their general class. In Table 1.8 are listed characteristic groups that are cited only as prefixes (never as suffixes) in substitutive nomenclature. The order of listing has no significance for nomenclature purposes. Systematic names formed by applying the principles of substitutive nomenclature are single words except for compounds named as acids. First one selects the parent compound, and thus the suffix, from the characteristic group listed earliest in Table 1.7. All remaining functional groups are handled as prefixes that precede, in alphabetical order, the parent name. Two examples may be helpful:

Structure I

Structure II

Structure I contains an ester group and an ether group. Since the ester group has higher priority, the name is ethyl 2-methoxy-6-methyl-3-cyclohexene-1-carboxylate. Structure II contains a carbonyl group, a hydroxy group, and a bromo group. The latter is never a suffix. Between the other two, the carbonyl group has higher priority, the parent has -one as suffix, and the name is 4-bromo-1-hydroxy2-butanone.

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Selection of the principal alicyclic chain or ring system is governed by these selection rules:

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1. For purely alicyclic compounds, the selection process proceeds successively until a decision is reached: (a) the maximum number of substituents corresponding to the characteristic group cited earliest in Table 1.7, (b) the maximum number of double and triple bonds considered together, (c) the maximum length of the chain, and (d) the maximum number of double bonds. Additional criteria, if needed for complicated compounds, are given in the IUPAC nomenclature rules. 2. If the characteristic group occurs only in a chain that carries a cyclic substituent, the compound is named as an aliphatic compound into which the cyclic component is substituted; a radical prefix is used to denote the cyclic component. This chain need not be the longest chain. 3. If the characteristic group occurs in more than one carbon chain and the chains are not directly

TABLE 1.7 Characteristic Groups for Substitutive Nomenclature Listed in order of decreasing priority for citation as principal group or parent name. Class

Formula*

1. Cations: H4N⫹ H3O⫹ H3S⫹ H3Se⫹ H2Cl⫹ H2Br⫹ H2I⫹ 2. Acids: Carboxylic

Sulfonic Sulfinic Sulfenic Salts

3. Derivatives of acids: Anhydrides Esters Acid halides Amides

9 COOH 9 (C)OOH 9 C( " O)OOH 9 (C " O)OOH 9 SO3H 9 SO2H 9 SOH 9 COOM 9 (C)OOM 9 SO3M 9 SO2M 9 SOM

9 C( " O)OC( " O) 9 9 (C " O)O(C " O) 9 9 COOR 9 C(OOR) 9 CO 9 halogen 9 CO 9 NH2 (C)O 9 NH2

Prefix

Suffix

-onioAmmonioOxonioSulfonioSelenonioChloronioBromonioIodonio-

-onium -ammonium -oxonium -sulfonium -selenonium -chloronium -bromonium -iodonium

Carboxy-

-carboxylic acid -oic acid -peroxy···carboxylic acid -peroxy···oic acid -sulfonic acid -sulfinic acid -sulfenic acid Metal···carboxylate Metal···oate Metal···sulfonate Metal···sulfinate Metal···sulfenate

SulfoSulfinoSulfeno-

R-oxycarbonylHaloformyl Carbamoyl-

-carboxylic anhydride -oic anhydride R···carboxylate R···oate -carbonyl halide -carboxamide -amide

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TABLE 1.7 Characteristic Groups for Substitutive Nomenclature (Continued) Class Hydrazides

Imides Amidines 4. Nitrile (cyanide) 5. Aldehydes

6. Ketones 7. Alcohols (and phenols) Thiols 8. Hydroperoxides 9. Amines Imines Hydrazines 10. Ethers Sulfides 11. Peroxides

Formula*

Prefix

9 CO 9 NHNH2

Carbonylhydrazino-

9 (CO) 9 NHNH2 9 CO 9 NH 9 CO 9 9 C( " NH) 9 NH2 9 (C " NH) 9 NH2 9 CN 9 (C)N 9 CHO 9 (C " O)H (then their analogs and

R-imidoAmidinoCyanoFormylOxoderivatives)

(C " O) Oxo(then their analogs and derivatives)

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Suffix -carbohydrazide -ohydrazide -carboximide -carboxamidine -amidine -carbonitrile -nitrile -carbaldehyde -al -one

9 OH

Hydroxy-

-ol

9 SH 9 O 9 OH 9 NH2 NH 9 NHNH2 9 OR 9 SR 9 O 9 OR

MercaptoHydroperoxyAminoIminoHydrazinoR-oxyR-thioR-dioxy-

-thiol -amine -imine -hydrazine

* Carbon atoms enclosed in parentheses are included in the name of the parent compound and not in the suffix or prefix.

TABLE 1.8 Characteristic Groups Cited Only as Prefixes in Substitutive Nomenclature Characteristic group

Prefix

9 Br

Bromo-

9 Cl 9 ClO 9 ClO2 9 ClO3 9F 9I 9 IO 9 IO2 9 I(OH)2

ChloroChlorosylChlorylPerchlorylFluoroIodoIodosylIodyl* Dihydroxyiodo-

* Formerly iodoxy.

Characteristic group

Prefix

9 IX2

X may be halogen or a radical; dihalogenoiodoor diacetoxyiodo-, e.g., 9 ICl2 is dichloroido-

N2 9 N3 9 NO 9 NO2 N(" O)OH 9 OR 9 SR 9 SeR ( 9 TeR)

DiazoAzidoNitrosoNitroaci-NitroR-oxyR-thioR-seleno- (R-telluro-)

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attached to one another, then the chain chosen as parent should carry the largest number of the characteristic group. If necessary, the selection is continued as in rule 1.

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4. If the characteristic group occurs only in one cyclic system, that system is chosen as the parent. 5. If the characteristic group occurs in more than one cyclic system, that system is chosen as parent which (a) carries the largest number of the principal group or, failing to reach a decision, (b) is the senior ring system. 6. If the characteristic group occurs both in a chain and in a cyclic system, the parent is that portion in which the principal group occurs in largest number. If the numbers are the same, that portion is chosen which is considered to be the most important or is the senior ring system. 7. When a substituent is itself substituted, all the subsidiary substituents are named as prefixes and the entire assembly is regarded as a parent radical. 8. The seniority of ring systems is ascertained by applying the following rules successively until a decision is reached: (a) all heterocycles are senior to all carbocycles, (b) for heterocycles, the preference follows the decision process described under Heterocyclic Systems, p. 1.11, (c) the largest number of rings, (d) the largest individual ring at the first point of difference, (e) the largest number of atoms in common among rings, (f) the lowest letters in the expression for ring functions, (g) the lowest numbers at the first point of difference in the expression for ring junctions, (h) the lowest state of hydrogenation, (i) the lowest-numbered locant for indicated hydrogen, (j) the lowest-numbered locant for point of attachment (if a radical), (k) the lowest-numbered locant for an attached group expressed as a suffix, (l) the maximum number of substituents cited as prefixes, (m) the lowest-numbered locant for substituents named as prefixes, hydro prefixes, -ene, and -yne, all considered together in one series in ascending numerical order independent of their nature, and (n) the lowest-numbered locant for the substituent named as prefix which is cited first in the name. Numbering of Compounds. If the rules for aliphatic chains and ring systems leave a choice, the starting point and direction of numbering of a compound are chosen so as to give lowest-numbered locants to these structural factors, if present, considered successively in the order listed below until a decision is reached. Characteristic groups take precedence over multiple bonds. 1. Indicated hydrogen, whether cited in the name or omitted as being conventional 2. Characteristic groups named as suffix following the ranking order of Table 1.7 3. Multiple bonds in acyclic compounds; in bicycloalkanes, tricycloalkanes, and polycycloalkanes, double bonds having priority over triple bonds; and in heterocyclic systems whose names end in -etine, -oline, or -olene 4. The lowest-numbered locant for substituents named as prefixes, hydro prefixes, -ene, and -yne, all considered together in one series in ascending numerical order 5. The lowest locant for that substituent named as prefix which is cited first in the name For cyclic radicals, indicated hydrogen and thereafter the point of attachment (free valency) have priority for the lowest available number. Prefixes and Affixes. Prefixes are arranged alphabetically and placed before the parent name; multiplying affixes, if necessary, are inserted and do not alter the alphabetical order already attained. The parent name includes any syllables denoting a change of ring member or relating to the structure of a carbon chain. Nondetachable parts of parent names include

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1. Forming rings; cyclo-, bicyclo-, spiro2. Fusing two or more rings: benzo-, naphtho-, imidazo3. Substituting one ring or chain member atom for another: oxa-, aza-, thia4. Changing positions of ring or chain members: iso-, sec-, tert-, neo5. Showing indicated hydrogen 6. Forming bridges: ethano-, epoxy7. HydroPrefixes that represent complete terminal characteristic groups are preferred to those representing only a portion of a given group. For example, for the prefix 9 C( "O)CH3 , the name (formylmethyl) is preferred to (oxoethyl). The multiplying affixes di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, undeca-, and so on are used to indicate a set of identical unsubstituted radicals or parent compounds. The forms bis-, tris-, tetrakis-, pentakis-, and so on are used to indicate a set of identical radicals or parent compounds each substituted in the same way. The affixes bi-, ter-, quater-, quinque-, sexi-, septi-, octi-, novi-, deci-, and so on are used to indicate the number of identical rings joined together by a single or double bond. Although multiplying affixes may be omitted for very common compounds when no ambiguity is caused thereby, such affixes are generally included throughout this handbook in alphabetical listings. An example would be ethyl ether for diethyl ether. 1.1.2.2 Conjunctive Nomenclature. Conjunctive nomenclature may be applied when a principal group is attached to an acyclic component that is directly attached by a carbon-carbon bond to a cyclic component. The name of the cyclic component is attached directly in front of the name of the acyclic component carrying the principal group. This nomenclature is not used when an unsaturated side chain is named systematically. When necessary, the position of the side chain is indicated by a locant placed before the name of the cyclic component. For substituents on the acyclic chain, carbon atoms of the side chain are indicated by Greek letters proceeding from the principal group to the cyclic component. The terminal carbon atom of acids, aldehydes, and nitriles is omitted when allocating Greek positional letters. Conjunctive nomenclature is not used when the side chain carries more than one of the principal group, except in the case of malonic and succinic acids. The side chain is considered to extend only from the principal group to the cyclic component. Any other chain members are named as substituents, with appropriate prefixes placed before the name of the cyclic component. When a cyclic component carries more than one identical side chain, the name of the cyclic component is followed by di-, tri-, etc., and then by the name of the acyclic component, and it is preceded by the locants for the side chains. Examples are

4-Methyl-1-cyclohexaneethanol

␣-Ethyl-␤, ␤-dimethylcyclohexaneethanol short standard long

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When side chains of two or more different kinds are attached to a cyclic component, only the senior side chain is named by the conjunctive method. The remaining side chains are named as prefixes. Likewise, when there is a choice of cyclic component, the senior is chosen. Benzene derivatives may be named by the conjunctive method only when two or more identical side chains are present. Trivial names for oxo carboxylic acids may be used for the acyclic component. If the cyclic and acyclic components are joined by a double bond, the locants of this bond are placed as superscripts to a Greek capital delta that is inserted between the two names. The locant for the cyclic component precedes that for the acyclic component, e.g., indene-⌬1,␣-acetic acid.

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1.1.2.3 Radicofunctional Nomenclature. The procedures of radicofunctional nomenclature are identical with those of substitutive nomenclature except that suffixes are never used. Instead, the functional class name (Table 1.9) of the compound is expressed as one word and the remainder of the molecule as another that precedes the class name. When the functional class name refers to a characteristic group that is bivalent, the two radicals attached to it are each named, and when different, they are written as separate words arranged in alphabetical order. When a compound contains more than one kind of group listed in Table 1.9, that kind is cited as the functional group or class name that occurs higher in the table, all others being expressed as prefixes. Radicofunctional nomenclature finds some use in naming ethers, sulfides, sulfoxides, sulfones, selenium analogs of the preceding three sulfur compounds, and azides.

TABLE 1.9 Functional Class Names Used in Radicofunctional Nomenclature Groups are listed in order of decreasing priority. Group X in acid derivatives

9 CN, 9 NC CO 9 OH 9 O 9 OH O S, SO, SO2 Se, SeO, SeO2 9 F, 9 Cl, 9 Br, 9 I 9 N3

Functional class names Name of X (in priority order: fluoride, chloride, bromide, iodide, cyanide, azide; then the sulfur and selenium analogs) Cyanide, isocyanide Ketone; then S and Se analogs Alcohol; then S and Se analogs Hydroperoxide Ether or oxide Sulfide, sulfoxide, sulfone Selenide, selenoxide, selenone Fluoride, chloride, bromide, iodide Azide

1.1.2.4 Replacement Nomenclature. Replacement nomenclature is intended for use only when other nomenclature systems are difficult to apply in the naming of chains containing heteroatoms. When no group is present that can be named as a principal group, the longest chain of carbon and heteroatoms terminating with carbon is chosen and named as though the entire chain were that of an acyclic hydrocarbon. The heteroatoms within this chain are identified by means of prefixes aza-, oxa-, thia-, etc., in the order of priority stated in Table 1.3. Locants indicate the positions of the heteroatoms in the chain. Lowest-numbered locants are assigned to the principal group when

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such is present. Otherwise, lowest-numbered locants are assigned to the heteroatoms considered together and, if there is a choice, to the heteroatoms cited earliest in Table 1.3. An example is

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13-Hydroxy-9,12-dioxa-3,6-diazatridecanoic acid

1.1.3

Specific Functional Groups

Characteristic groups will now be treated briefly in order to expand the terse outline of substitutive nomenclature presented in Table 1.7. Alternative nomenclature will be indicated whenever desirable. 1.1.3.1 Acetals and Acylals. Acetals, which contain the group ⬎C(OR)2 , where R may be different, are named (1) as dialkoxy compounds or (2) by the name of the corresponding aldehyde or ketone followed by the name of the hydrocarbon radical(s) followed by the word acetal. For example, CH3 9 CH(OCH3 )2 is named either (1) 1,1-dimethoxyethane or (2) acetaldehyde dimethyl acetal. A cyclic acetal in which the two acetal oxygen atoms form part of a ring may be named (1) as a heterocyclic compound or (2) by use of the prefix methylenedioxy for the group 9O9CH2 9 O 9 as a substituent in the remainder of the molecule. For example, (1) 1,3-Benzo[d]dioxole-5-carboxylic acid (2) 3,4-Methylenedioxybenzoic acid Acylals, R1R2C(OCOR3 )2 , are named as acid esters;

Butylidene acetate propionate

␣-Hydroxy ketones, formerly called acyloins, had been named by changing the ending -ic acid or -oic acid of the corresponding acid to -oin. They are preferably named by substitutive nomenclature; thus CH3 9CH(OH)9CO9 CH3

3-Hydroxy-2-butanone (formerly acetoin)

1.1.3.2 Acid Anhydrides. Symmetrical anhydrides of monocarboxylic acids, when unsubstituted, are named by replacing the word acid by anhydride. Anhydrides of substituted monocarboxylic acids, if symmetrically substituted, are named by prefixing bis- to the name of the acid and replacing the word acid by anhydride. Mixed anhydrides are named by giving in alphabetical order the first part of the names of the two acids followed by the word anhydride, e.g., acetic propionic anhydride or acetic propanoic anhydride. Cyclic anhydrides of polycarboxylic acids, although possessing a

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heterocyclic structure, are preferably named as acid anhydrides. For example,

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1,8;4,5-Napthalenetetracarboxylic dianhydride (note the use of a semicolon to distinguish the pairs of locants)

1.1.3.3 Acyl Halides. Acyl halides, in which the hydroxyl portion of a carboxyl group is replaced by a halogen, are named by placing the name of the corresponding halide after that of the acyl radical. When another group is present that has priority for citation as principal group or when the acyl halide is attached to a side chain, the prefix haloformyl- is used as, for example, in fluoroformyl-. 1.1.3.4 Alcohols and Phenols. The hydroxyl group is indicated by a suffix -ol when it is the principal group attached to the parent compound and by the prefix hydroxy- when another group with higher priority for citation is present or when the hydroxy group is present in a side chain. When confusion may arise in employing the suffix -ol, the hydroxy group is indicated as a prefix; this terminology is also used when the hydroxyl group is attached to a heterocycle, as, for example, in the name 3-hydroxythiophene to avoid confusion with thiophenol (C6H5SH). Designations such as isopropanol, sec-butanol, and tert-butanol are incorrect because no hydrocarbon exists to which the suffix can be added. Many trivial names are retained. These structures are shown in Table 1.10. The radicals (RO9) are named by adding -oxy as a suffix to the name of the R radical, e.g., pentyloxy for CH3CH2CH2CH2CH2O 9. These contractions are exceptions: methoxy (CH3O 9), ethoxy (C2H5O 9 ), propoxy (C3H7 O 9), butoxy (C4H9O 9), and phenoxy (C6H5O 9). For unsubstituted radicals only, one may use isopropoxy [(CH3 )2CH9O 9 ], isobutoxy [(CH3 )2CH2CH9O 9 ], sec-butoxy [CH3CH2CH(CH3 ) 9O 9], and tert-butoxy [(CH3 )3C9 O 9].

TABLE 1.10 Retained Trivial Names of Alcohols and Phenols with Structures Ally alcohol tert-Butyl alcohol Benzyl alcohol Phenethyl alcohol Ethylene glycol 1,2-Propylene glycol Glycerol Pentaerythritol Pinacol Phenol

CH2 " CHCH2OH (CH3)3COH C6H5CH2OH C6H5CH2CH2OH HOCH2CH2OH CH3CHOHCH2OH HOCH2CHOHCH2OH C(CH2OH)4 (CH3)2COHCOH(CH3)2 C6H5OH OH

Xylitol

HOCH2CH 9 CH 9 CH 9 CH2OH

Geraniol

(CH3)2C " CHCH2CH2C " CHCH2OH

OH

OH

CH3

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TABLE 1.10 Retained Trivial Names of Alcohols and Phenols with Structures (Continued)

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Bivalent radicals of the form O9Y 9O are named by adding -dioxy to the name of the bivalent radicals except when forming part of a ring system. Examples are 9 O 9CH2 9 O 9 (methylenedioxy), 9 O 9 CO9 O 9 (carbonyldioxy), and 9O 9 SO2 9O 9 (sulfonyldioxy). Anions derived from alcohols or phenols are named by changing the final -ol to -olate. Salts composed of an anion, RO9 , and a cation, usually a metal, can be named by citing first the cation and then the RO anion (with its ending changed to -yl oxide), e.g., sodium benzyl oxide for C6H5CH2ONa. However, when the radical has an abbreviated name, such as methoxy, the ending -oxy is changed to -oxide. For example, CH3ONa is named sodium methoxide (not sodium methylate).

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1.1.3.5 Aldehydes. When the group 9 C( "O)H, usually written 9 CHO, is attached to carbon at one (or both) end(s) of a linear acyclic chain the name is formed by adding the suffix -al (or -dial) to the name of the hydrocarbon containing the same number of carbon atoms. Examples are butanal for CH3CH2CH2CHO and propanedial for, OHCCH2CHO. Naming an acyclic polyaldehyde can be handled in two ways. First, when more than two aldehyde groups are attached to an unbranched chain, the proper affix is added to -carbaldehyde, which becomes the suffix to the name of the longest chain carrying the maximum number of aldehyde groups. The name and numbering of the main chain do not include the carbon atoms of the aldehyde groups. Second, the name is formed by adding the prefix formyl- to the name of the -dial that incorporates the principal chain. Any other chains carrying aldehyde groups are named by the use of formylalkyl- prefixes. Examples are

(1) 1,2,5-Pentanetricarbaldehyde (2) 3-Formylheptanedial

(1) 4-(2-Formylethyl)-3-(formylmethyl)-1,2,7-heptanetricarbaldehyde (2) 3-Formyl-5-(2-formylethyl)-4-(formylmethyl)nonanedial When the aldehyde group is directly attached to a carbon atom of a ring system, the suffix -carbaldehyde is added to the name of the ring system, e.g., 2-naphthalenecarbaldehyde. When the aldehyde group is separated from the ring by a chain of carbon atoms, the compound is named (1) as a derivative of the acyclic system or (2) by conjunctive nomenclature, for example, (1) (2-naphthyl)propionaldehyde or (2) 2-naphthalenepropionaldehyde. An aldehyde group is denoted by the prefix formyl- when it is attached to a nitrogen atom in a ring system or when a group having priority for citation as principal group is present and part of a cyclic system. When the corresponding monobasic acid has a trivial name, the name of the aldehyde may be formed by changing the ending -ic acid or -oic acid to -aldehyde. Examples are Formaldehyde

Acrylaldehyde (not acrolein)

Acetaldehyde

Benzaldehyde

Propionaldehyde

Cinnamaldehyde

Butyraldehyde

2-Furaldehyde (not furfural)

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The same is true for polybasic acids, with the proviso that all the carboxyl groups must be changed to aldehyde; then it is not necessary to introduce affixes. Examples are Glyceraldehyde

Succinaldehyde

Glycolaldehyde

Phthalaldehyde (o-, m-, p-)

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Malonaldehyde These trivial names may be retained: citral (3,7-dimethyl-2,6-octadienal), vanillin (4-hydroxy-3methoxybenzaldehyde), and piperonal (3,4-methylenedioxybenzaldehyde). 1.1.3.6 Amides. For primary amides the suffix -amide is added to the systematic name of the parent acid. For example, CH3 9CO9NH2 is acetamide. Oxamide is retained for H2N 9CO9 CO9NH2 . The name -carboxylic acid is replaced by -carboxamide. For amino acids having trivial names ending in -ine, the suffix -amide is added after the name of the acid (with elision of e for monoamides). For example, H2N 9CH2 9CO9NH2 is glycinamide. In naming the radical R9 CO9 NH 9, either (1) the -yl ending of RCO 9 is changed to -amido or (2) the radicals are named as acylamino radicals. For example, (1) 4-Acetamidobenzoic acid (2) 4-Acetylaminobenzoic acid The latter nomenclature is always used for amino acids with trivial names. N-substituted primary amides are named either (1) by citing the substituents as N prefixes or (2) by naming the acyl group as an N substituent of the parent compound. For example, (1) N-Methylbenzamide (2) Benzoylaminomethane 1.1.3.7 Amines. Amines are preferably named by adding the suffix -amine (and any multiplying affix) to the name of the parent radical. Examples are CH3CH2CH2CH2CH2NH2 H2NCH2CH2CH2CH2CH2NH2

Pentylamine 1,5-Pentyldiamine or pentamethylenediamine

Locants of substituents of symmetrically substituted derivatives of symmetrical amines are distinguished by primes or else the names of the complete substituted radicals are enclosed in parentheses. Unsymmetrically substituted derivatives are named similarly or as N-substituted products of a primary amine (after choosing the most senior of the radicals to be the parent amine). For example, (1) 1,3⬘-Difluorodipropylamine (2) 1-Fluoro-N-(3-fluoropropyl)propylamine (3) (1-Fluoropropyl)(3-fluoropropyl)amine Complex cyclic compounds may be named by adding the suffix -amine or the prefix amino- (or aminoalkyl-) to the name of the parent compound. Thus three names are permissible for (1) 4-Pyridylamine (2) 4-Pyridinamine (3) 4-Aminopyridine

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Complex linear polyamines are best designated by replacement nomenclature. These trivial names are retained: aniline, benzidene, phenetidine, toluidine, and xylidine. The bivalent radical 9NH 9 linked to two identical radicals can be denoted by the prefix imino-, as well as when it forms a bridge between two carbon ring atoms. A trivalent nitrogen atom linked to three identical radicals is denoted by the prefix nitrilo-. Thus ethylenediaminetetraacetic acid (an allowed exception) should be named ethylenedinitrilotetraacetic acid.

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1.1.3.8 Ammonium Compounds. Salts and hydroxides containing quadricovalent nitrogen are named as a substituted ammonium salt or hydroxide. The names of the substituting radicals precede the word ammonium, and then the name of the anion is added as a separate word. For example, (CH3 )4N⫹I⫺ is tetramethylammonium iodide. When the compound can be considered as derived from a base whose name does not end in -amine, its quaternary nature is denoted by adding ium to the name of that base (with elision of e), substituent groups are cited as prefixes, and the name of the anion is added separately at the end. Examples are C6H5NH⫹3 HSO4⫺ ⫹

Anilinium hydrogen sulfate 2⫺ 6

[(C6H5NH3 ) ]2 PtCl

Dianilinium hexachloroplatinate

The names choline and betaine are retained for unsubstituted compounds. In complex cases, the prefixes amino- and imino- may be changed to ammonio- and iminio- and are followed by the name of the molecule representing the most complex group attached to this nitrogen atom and are preceded by the names of the other radicals attached to this nitrogen. Finally the name of the anion is added separately. For example, the name might be 1-trimethylammonioacridine chloride or 1-acridinyltrimethylammonium chloride. When the preceding rules lead to inconvenient names, then (1) the unaltered name of the base may be used followed by the name of the anion or (2) for salts of hydrohalogen acids only the unaltered name of the base is used followed by the name of the hydrohalide. An example of the latter would be 2-ethyl-p-phenylenediamine monohydrochloride. 1.1.3.9 Azo Compounds. When the azo group (9N " N 9) connects radicals derived from identical unsubstituted molecules, the name is formed by adding the prefix azo- to the name of the parent unsubstituted molecules. Substituents are denoted by prefixes and suffixes. The azo group has priority for lowest-numbered locant. Examples are azobenzene for C6H5 9N "N 9C6H5 , azobenzene-4-sulfonic acid for C6H5 9N "N 9 C6H5SO3H, and 2⬘,4-dichloroazobenzene-4⬘-sulfonic acid for ClC6H4 9 N " N 9C6H3ClSO3H. When the parent molecules connected by the azo group are different, azo is placed between the complete names of the parent molecules, substituted or unsubstituted. Locants are placed between the affix azo and the names of the molecules to which each refers. Preference is given to the more complex parent molecule for citation as the first component, e.g., 2-aminonaphthalene-1-azo(4⬘-chloro-2⬘-methylbenzene). In an alternative method, the senior component is regarded as substituted by RN" N 9, this group R being named as a radical. Thus 2-(7-phenylazo-2-naphthylazo)anthracene is the name by this alternative method for the compound named anthracene-2-azo-2⬘-naphthalene-7⬘-azobenzene. 1.1.3.10 Azoxy Compounds. Where the position of the azoxy oxygen atom is unknown or immaterial, the compound is named in accordance with azo rules, with the affix azo replaced by azoxy. When the position of the azoxy oxygen atom in an unsymmetrical compound is designated, a prefix NNO- or ONN- is used. When both the groups attached to the azoxy radical are cited in the name of the compound, the prefix NNO- specifies that the second of these two groups is attached directly

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to 9N(O)9 ; the prefix ONN- specifies that the first of these two groups is attached directly to 9N(O)9. When only one parent compound is cited in the name, the prefixed ONN- and NNOspecify that the group carrying the primed and unprimed substituents is connected, respectively, to the 9 N(O) 9 group. The prefix NON- signifies that the position of the oxygen atom is unknown; the azoxy group is then written as 9N2O 9. For example,

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2,2⬘,4-Trichloro-NNO-azoxybenzene

1.1.3.11 Boron Compounds. Molecular hydrides of boron are called boranes. They are named by using a multiplying affix to designate the number of boron atoms and adding an Arabic numeral within parentheses as a suffix to denote the number of hydrogen atoms present. Examples are pentaborane(9) for B5H9 and pentaborane(11) for B5H11 . Organic ring systems are named by replacement nomenclature. Three- to ten-membered monocyclic ring systems containing uncharged boron atoms may be named by the specialist nomenclature for heterocyclic systems. Organic derivatives are named as outlined for substitutive nomenclature. The complexity of boron nomenclature precludes additional details; the text by Rigaudy and Klesney should be consulted. 1.1.3.12 Carboxylic Acids. Carboxylic acids may be named in several ways. First, 9COOH groups replacing CH3 9 at the end of the main chain of an acyclic hydrocarbon are denoted by adding -oic acid to the name of the hydrocarbon. Second, when the 9COOH group is the principal group, the suffix -carboxylic acid can be added to the name of the parent chain whose name and chain numbering does not include the carbon atom of the 9COOH group. The former nomenclature is preferred unless use of the ending -carboxylic acid leads to citation of a larger number of carboxyl groups as suffix. Third, carboxyl groups are designated by the prefix carboxy- when attached to a group named as a substituent or when another group is present that has higher priority for citation as principal group. In all cases, the principal chain should be linked to as many carboxyl groups as possible even though it might not be the longest chain present. Examples are CH3CH2CH2CH2CH2CH2 COOH

(1) Heptanoic acid (2) 1-Hexanecarboxylic acid

C6H11COOH

(2) Cyclohexanecarboxylic acid

(3) 2-(Carboxymethyl)-1,4-hexanedicarboxylic acid Removal of the OH from the 9 COOH group to form the acyl radical results in changing the ending -oic acid to -oyl or the ending -carboxylic acid to -carbonyl. Thus the radical CH3CH2CH2CH2CO9 is named either pentanoyl or butanecarbonyl. When the hydroxyl has not been removed from all carboxyl groups present in an acid, the remaining carboxyl groups are denoted by the prefix carboxy-. For example, HOOCCH2CH2CH2CH2CH2CO9 is named 6-carboxyhexanoyl.

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TABLE 1.11 Names of Some Carboxylic Acids Systematic name

Trivial name

Methanoic Ethanoic Propanoic Butanoic 2-Methylpropanoic Pentanoic 3-Methylbutanoic 2,2-Dimethylpropanoic Hexanoic Heptanoic Octanoic Decanoic Dodecanoic Tetradecanoic Hexadecanoic Octadecanoic

Formic Acetic Propionic Butyric Isobutyric* Valeric Isovaleric* Pivalic* (Caproic) (Enanthic) (Caprylic) (Capric) Lauric* Myristic* Palmitic* Stearic*

Ethanedioic Propanedioic Butanedioic Pentanedioic Hexanedioic Heptanedioic Octanedioic Nonanedioic Decanedioic Propenoic Propynoic 2-Methylpropenoic trans-2-Butenoic cis-2-Butenoic cis-9-Octadecenoic trans-9-Octadecenoic cis-Butenedioic trans-Butenedioic cis-Methylbutenedioic

Oxalic Malonic Succinic Glutaric Adipic Pimelic* Suberic* Azelaic* Sebacic* Acrylic Propiolic Methacrylic Crotonic Isocrotonic Oleic Elaidic Maleic Fumaric Citraconic*

Systematic name

Trivial name

trans-Methylbutenedioic

Mesaconic*

1,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acid

Camphoric

Benzenecarboxylic 1,2-Benzenedicarboxylic 1,3-Benzenedicarboxylic 1,4-Benzenedicarboxylic Naphthalenecarboxylic Methylbenzenecarboxylic 2-Phenylpropanoic 2-Phenylpropenoic trans-3-Phenylpropenoic Furancarboxylic Thiophenecarboxylic 3-Pyridinecarboxylic 4-Pyridinecarboxylic

Benzoic Phthalic Isophthalic Terephthalic Naphthoic Toluic Hydratropic Atropic Cinnamic Furoic Thenoic Nicotinic Isonicotinic

Hydroxyethanoic 2-Hydroxypropanoic 2,3-Dihydroxypropanoic Hydroxypropanedioic Hydroxybutanedioic 2,3-Dihydroxybutanedioic 3-Hydroxy-2-phenylpropanoic 2-Hydroxy-2,2-diphenylethanoic 2-Hydroxybenzoic Methoxybenzoic 4-Hydroxy-3-methoxybenzoic

Glycolic Lactic Glyceric Tartronic Malic Tartaric Tropic Benzilic Salicylic Anisic Vanillic

3,4-Dimethoxybenzoic 3,4-Methylenedioxybenzoic 3,4-Dihydroxybenzoic 3,4,5-Trihydroxybenzoic

Veratric Piperonylic Protocatechuic Gallic

* Systematic names should be used in derivatives formed by substitution on a carbon atom. Note: The names in parentheses are abandoned but are listed for reference to older literature.

Many trivial names exist for acids; these are listed in Table 1.11. Generally, radicals are formed by replacing -ic acid by -oyl.* When a trivial name is given to an acyclic monoacid or diacid, the numeral 1 is always given as locant to the carbon atom of a carboxyl group in the acid or to the carbon atom with a free valence in the radical RCO9. * Exceptions: formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, oxalyl, malonyl, succinyl, glutaryl, furoyl, and thenoyl.

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1.1.3.13 Ethers (R1 9 O 9R2). In substitutive nomenclature, one of the possible radicals, R9O 9, is stated as the prefix to the parent compound that is senior from among R1 or R2. Examples are methoxyethane for CH3OCH2CH3 and butoxyethanol for C4H9OCH2CH2OH. When another principal group has precedence and oxygen is linking two identical parent compounds, the prefix oxy- may be used, as with 2,2⬘-oxydiethanol for HOCH2CH2OCH2CH2OH. Compounds of the type RO9 Y9 OR, where the two parent compounds are identical and contain a group having priority over ethers for citation as suffix, are named as assemblies of identical units. For example, HOOC9CH2 9 O 9CH2CH2 9O 9CH2 9COOH is named 2,2⬘-(ethylenedioxy)diacetic acid. Linear polyethers derived from three or more molecules of aliphatic dihydroxy compounds, particularly when the chain length exceeds ten units, are most conveniently named by open-chain replacement nomenclature. For example, CH3CH2 9 O 9 CH2CH2 9O 9CH2CH3 could be 3,6dioxaoctane or (2-ethoxy)ethoxyethane. An oxygen atom directly attached to two carbon atoms already forming part of a ring system or to two carbon atoms of a chain may be indicated by the prefix epoxy-. For example, CH2 9 CH 9 CH2Cl is named 1-chloro-2,3-epoxypropane.

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O Symmetrical linear polyethers may be named (1) in terms of the central oxygen atom when there is an odd number of ether oxygen atoms or (2) in terms of the central hydrocarbon group when there is an even number of ether oxygen atoms. For example, C2H5 9 O 9 C4H8 9O 9C4H8 9O 9C2H5 is bis-(4-ethoxybutyl)ether, and 3,6-dioxaoctane (earlier example) could be named 1,2bis(ethoxy)ethane. Partial ethers of polyhydroxy compounds may be named (1) by substitutive nomenclature or (2) by stating the name of the polyhydroxy compound followed by the name of the etherifying radical(s) followed by the word ether. For example, (1) 3-Butoxy-1,2-propanediol (2) Glycerol 1-butyl ether; also, 1-O-butylglycerol

Cyclic ethers are named either as heterocyclic compounds or by specialist rules of heterocyclic nomenclature. Radicofunctional names are formed by citing the names of the radicals R1 and R2 followed by the word ether. Thus methoxyethane becomes ethyl methyl ether and ethoxyethane becomes diethyl ether. 1.1.3.14 Halogen Derivatives. Using substitutive nomenclature, names are formed by adding prefixes listed in Table 1.8 to the name of the parent compound. The prefix perhalo- implies the replacement of all hydrogen atoms by the particular halogen atoms. Cations of the type R1R2X⫹ are given names derived from the halonium ion, H2X⫹, by substitution, e.g., diethyliodonium chloride for (C2H5 )2I⫹Cl⫺. Retained are these trivial names; bromoform (CHBr3 ), chloroform (CHCl3 ), fluoroform (CHF3 ), iodoform (CHI3 ), phosgene (COCl2 ), thiophosgene (CSCl2 ), and dichlorocarbene radical ( CCl2). Inorganic nomenclature leads to such names as carbonyl and thiocarbonyl halides (COX2 and CSX2 ) and carbon tetrahalides (CX4 ). 1.1.3.15 Hydroxylamines and Oximes. For RNH 9OH compounds, prefix the name of the radical R to hydroxylamine. If another substituent has priority as principal group, attach the prefix

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hydroxyamino- to the parent name. For example, C6H5NHOH would be named N-phenylhydroxylamine, but HOC6H4NHOH would be (hydroxyamino)phenol, with the point of attachment indicated by a locant preceding the parentheses. Compounds of the type R1NH9OR2 are named (1) as alkoxyamino derivatives of compound 1 R H, (2) as N,O-substituted hydroxylamines, (3) as alkoxyamines (even if R1 is hydrogen), or (4) by the prefix aminooxy- when another substituent has priority for parent name. Examples of each type are

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1. 2-(Methoxyamino)-8-naphthalenecarboxylic acid for CH3ONH9C10H6COOH 2. O-Phenylhydroxylamine for H2N 9O 9 C6H5 or N-phenylhydroxylamine for C6H5NH 9OH 3. Phenoxyamine for H2N 9 O 9C6H5 (not preferred to O-phenylhydroxylamine) 4. Ethyl (aminooxy)acetate for H2N 9 O 9CH2CO9 OC2H5 Acyl derivatives, RCO9NH 9 OH and H2N 9O 9CO9 R, are named as N-hydroxy derivatives of amides and as O-acylhydroxylamines, respectively. The former may also be named as hydroxamic acids. Examples are N-hydroxyacetamide for CH3CO9NH9OH and O-acetylhydroxylamine for H2N 9 O 9 CO9 CH3 . Further substituents are denoted by prefixes with O- and/or Nlocants. For example, C6H5NH 9 O 9C2H5 would be O-ethyl-N-phenylhydroxylamine or N-ethoxylaniline. For oximes, the word oxime is placed after the name of the aldehyde or ketone. If the carbonyl group is not the principal group, use the prefix hydroxyimino-. Compounds with the group N 9 OR are named by a prefix alkyloxyimino- as oxime O-ethers or as O-substituted oximes. Compounds with the group C " N(O)R are named by adding N-oxide after the name of the alkylideneaminc compound. For amine oxides, add the word oxide after the name of the base, with locants. For example, C5H5N 9 O is named pyridine N-oxide or pyridine 1-oxide. 1.1.3.16 Imines. The group ⬎C"NH is named either by the suffix -imine or by citing the name of the bivalent radical R1R2C⬍ as a prefix to amine. For example, CH3CH2CH2CH"NH could be named 1-butanimine or butylideneamine. When the nitrogen is substituted, as in CH2 "N9CH2CH3 , the name is N-(methylidene)ethylamine. Quinones are exceptions. When one or more atoms of quinonoid oxygen have been replaced by ⬎NH or ⬎NR, they are named by using the name of the quinone followed by the word imine (and preceded by proper affixes). Substituents on the nitrogen atom are named as prefixes. Examples are

p-Benzoquinone monoimine p-Benzoquinone diimine

1.1.3.17 Ketenes. Derivatives of the compound ketene, CH2 "C"O, are named by substitutive nomenclature. For example, C4H9CH"C"O is butyl ketene. An acyl derivative, such as CH3CH2 9 CO9 CH2CH" C" O, may be named as a polyketone, 1-hexene-1,4-dione. Bisketene is used for two to avoid ambiguity with diketene (dimeric ketene). 1.1.3.18 Ketones. Acyclic ketones are named (1) by adding the suffix -one to the name of the hydrocarbon forming the principal chain or (2) by citing the names of the radicals R1 and R2 followed

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by the word ketone. In addition to the preceding nomenclature, acyclic monoacyl derivatives of cyclic compounds may be named (3) by prefixing the name of the acyl group to the name of the cyclic compound. For example, the three possible names of

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(1) 1-(2-Furyl)-1-propanone (2) Ethyl 2-furyl ketone (3) 2-Propionylfuran

When the cyclic component is benzene or naphthalene, the -ic acid or -oic acid of the acid corresponding to the acyl group is changed to -ophenone or -onaphthone, respectively. For example, C6H5 9CO9CH2CH2CH3 can be named either butyrophenone (or butanophenone) or phenyl propyl ketone. Radicofunctional nomenclature can be used when a carbonyl group is attached directly to carbon atoms in two ring systems and no other substituent is present having priority for citation. When the methylene group in polycarbocyclic and heterocyclic ketones is replaced by a keto group, the change may be denoted by attaching the suffix -one to the name of the ring system. However, when ⱖCH in an unsaturated or aromatic system is replaced by a keto group, two alternative names become possible. First, the maximum number of noncumulative double bonds is added after introduction of the carbonyl group(s), and any hydrogen that remains to be added is denoted as indicated hydrogen with the carbonyl group having priority over the indicated hydrogen for lowernumbered locant. Second, the prefix oxo- is used, with the hydrogenation indicated by hydro prefixes; hydrogenation is considered to have occurred before the introduction of the carbonyl group. For example,

(1) 1-(2H)-Naphthalenone (2) 1-Oxo-1,2-dihydronaphthalene

When another group having higher priority for citation as principal group is also present, the ketonic oxygen may be expressed by the prefix oxo-, or one can use the name of the carbonylcontaining radical, as, for example, acyl radicals and oxo-substituted radicals. Examples are

4-(4⬘-Oxohexyl)-1-benzoic acid

1,2,4-Triacetylbenzene

Diketones and tetraketones derived from aromatic compounds by conversion of two or four CH groups into keto groups, with any necessary rearrangement of double bonds to a quinonoid structure, are named by adding the suffix -quinone and any necessary affixes. Polyketones in which two or more contiguous carbonyl groups have rings attached at each end

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may be named (1) by the radicofunctional method or (2) by substitutive nomenclature. For example,

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(1) 2-Naphthyl 2-pyridyl diketone (2) 1-(2-Naphthyl)-2-(2-pyridyl)ethanedione Some trivial names are retained: acetone (2-propanone), biacetyl (2,3-butanedione), propiophenone (C6H5 9CO9 CH2CH3 ), chalcone (C6H5 9 CH"CH9CO 9C6H5 ), and deoxybenzoin (C6H5 9 CH2 9CO 9 C6H5 ). These contracted names of heterocyclic nitrogen compounds are retained as alternatives for systematic names, sometimes with indicated hydrogen. In addition, names of oxo derivatives of fully saturated nitrogen heterocycles that systematically end in -idinone are often contracted to end in -idone when no ambiguity might result. For example,

2-Pyridone 2(1H)-Pyridone

4-Pyridone 4(1H)-Pyridone

1-Isoquinolone 1(2H)-Isoquinolone

5-Pyrazolone 5(4H)-Pyrazolone

2-Quinolone 2(1H)-Quinolone

4-Oxazolone 4(5H)-Oxazolone

4-Isoxazoline 4(5H)-Isoxazolone

4-Quinolone 4(1H)-Quinolone

4-Pyrazolone 4(5H)-Pyrazolone

4-Thiazolone 4(5H)-Thiazolone

9-Acridone 9(10H)-Acridone

1.1.3.19 Lactones, Lactides, Lactams, and Lactims. When the hydroxy acid from which water may be considered to have been eliminated has a trivial name, the lactone is designated by substituting -olactone for -ic acid. Locants for a carbonyl group are numbered as low as possible, even before that of a hydroxyl group. Lactones formed from aliphatic acids are named by adding -olide to the name of the nonhydroxylated hydrocarbon with the same number of carbon atoms. The suffix -olide signifies the change of CH CH3 into C C " O. O Structures in which one or more (but not all) rings of an aggregate are lactone rings are named by placing -carbolactone (denoting the 9O 9CO9 bridge) after the names of the structures that

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remain when each bridge is replaced by two hydrogen atoms. The locant for 9 CO9 is cited before that for the ester oxygen atom. An additional carbon atom is incorporated into this structure as compared to the -olide. These trivial names are permitted: ␥-butyrolactone, ␥-valerolactone, and ␦-valerolactone. Names based on heterocycles may be used for all lactones. Thus, ␥-butyrolactone is also tetrahydro-2furanone or dihydro-2(3H)-furanone. Lactides, intermolecular cyclic esters, are named as heterocycles. Lactams and lactims, containing a 9 CO9 NH 9 and 9 C(OH) " N 9 group, respectively, are named as heterocycles, but they may also be named with -lactam or -lactim in place of -olide. For example,

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(1) 2-Pyrrolidinone (2) 4-Butanelactam

1.1.3.20 Nitriles and Related Compounds. For acids whose systematic names end in -carboxylic acid, nitriles are named by adding the suffix -carbonitrile when the 9CN group replaces the 9 COOH group. The carbon atom of the 9CN group is excluded from the numbering of a chain to which it is attached. However, when the triple-bonded nitrogen atom is considered to replace three hydrogen atoms at the end of the main chain of an acyclic hydrocarbon, the suffix -nitrile is added to the name of the hydrocarbon. Numbering begins with the carbon attached to the nitrogen. For example, CH3CH2CH2CH2CH2CN is named (1) pentanecarbonitrile or (2) hexanenitrile. Trivial acid names are formed by changing the endings -oic acid or -ic acid to -onitrile. For example, CH3CN is acetonitrile. When the 9 CN group is not the highest priority group, the 9 CN group is denoted by the prefix cyano-. In order of decreasing priority for citation of a functional class name, and the prefix for substitutive nomenclature, are the following related compounds:

Functional group

Prefix

Radicofunctional ending

9 NC 9 OCN 9 NCO 9 ONC 9 SCN 9 NCS 9 SeCN 9 NCSe

IsocyanoCyanatoIsocyanato— ThiocyanatoIsothiocyanatoSelenocyanatoIsoselenocyanato-

Isocyanide Cyanate Isocyanate Fulminate Thiocyanate Isothiocyanate Selenocyanate Isoselenocyanate

1.1.3.21 Peroxides. Compounds of the type R9 O 9OH are named (1) by placing the name of the radical R before the word hydroperoxide or (2) by use of the prefix hydroperoxy- when another parent name has higher priority. For example, C2H5OOH is ethyl hydroperoxide. Compounds of the type R1O 9 OR2 are named (1) by placing the names of the radicals in alphabetical order before the word peroxide when the group 9O 9 O 9 links two chains, two rings, or a ring and a chain, (2) by use of the affix dioxy to denote the bivalent group 9 O 9O9 for naming assemblies of identical units or to form part of a prefix, or (3) by use of the prefix epidioxywhen the peroxide group forms a bridge between two carbon atoms, a ring, or a ring system.

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Examples are methyl propyl peroxide for CH3 9O 9O 9 C3H7 and 2,2⬘-dioxydiacetic acid for HOOC9 CH2 9O 9O 9 CH2 9 COOH.

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1.1.3.22 Phosphorus Compounds. Acyclic phosphorus compounds containing only one phosphorus atom, as well as compounds in which only a single phosphorus atom is in each of several functional groups, are named as derivatives of the parent structures listed in Table 1.12. Often these

TABLE 1.12 Parent Structures of Phosphorus-Containing Compounds

Formula

Parent name

H3P H5P

Phosphine Phosphorane

H3PO H3PS H3PNH P(OH)3 HP(OH)2 H2POH P(O)(OH)3 HP(O)(OH)2

Phosphine oxide Phosphine sulfide Phosphine imide Phosphorous acid Phosphonous acid Phosphinous acid Phosphoric acid Phosphonic acid

H2P(O)OH

Phosphinic acid

Substitutive prefix H2P 9 H4P 9 H3P H2P

PhosphinoPhosphoranylPhosphoroanediylPhosphoranetriyl-

PhosphorylP(O) PhosphonoylHP(O) 9 P(O)OH2 PhosphonoH2P(O) 9 PhosphinoylP(O)OH PhosphinocoPhosphinato-

Radicofunctional ending Phosphide

Phosphite Phosphonite Phosphinite Phosphate(V) Phosphonate Phosphinate

are purely hypothetical parent structures. When hydrogen attached to phosphorus is replaced by a hydrocarbon group, the derivative is named by substitution nomenclature. When hydrogen of an 9OH group is replaced, the derivative is named by radicofunctional nomenclature. For example, C2H5PH2 is ethylphosphine; (C2H5 )2PH, diethylphosphine; CH3P(OH)2 , dihydroxy-methyl-phosphine or methylphosphonous acid; C2H5 9 PO(Cl)(OH), ethylchlorophosphonic acid or ethylphosphonochloridic acid or hydrogen chlorodioxoethylphosphate(V); CH3CH(PH2 )COOH, 2-phosphinopropionic acid; HP(CH2COOH)2 , phosphinediyldiacetic acid; (CH3 )HP(O)OH, methylphosphinic acid or hydrogen hydridomethyldioxophosphate(V); (CH3O)3PO, trimethyl phosphate; and (CH3O)3P, trimethyl phosphite. 1.1.3.23 Salts and Esters of Acids. Neutral salts of acids are named by citing the cation(s) and then the anion, whose ending is changed from -oic to -oate or from -ic to -ate. When different acidic residues are present in one structure, prefixes are formed by changing the anion ending -ate to -atoor -ide to -ido-. The prefix carboxylato- denotes the ionic group 9COO⫺. The phrase (metal) salt of (the acid) is permissible when the carboxyl groups are not all named as affixes. Acid salts include the word hydrogen (with affixes, if appropriate) inserted between the name of the cation and the name of the anion (or word salt). Esters are named similarly, with the name of the alkyl or aryl radical replacing the name of the

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cation. Acid esters of acids and their salts are named as neutral esters, but the components are cited in the order: cation, alkyl or aryl radical, hydrogen, and anion. Locants are added if necessary. For example,

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Potassium 1-ethyl hydrogen citrate

Ester groups in R1 9CO9OR2 compounds are named (1) by the prefix alkoxycarbonyl- or aryloxycarbonyl- for 9 CO9OR2 when the radical R1 contains a substituent with priority for citation as principal group or (2) by the prefix acyloxy- for R1 9CO9O 9 when the radical R2 contains a substituent with priority for citation as principal group. Examples are

Methyl 3-methoxycarbonyl-2-naphthalenebutyrate

+ [CH3O9CO9CH2CH2N(CH3)3 ]Cl⫺

[(2-Methoxycarbonyl)ethyl]trimethylammonium chloride

C6H5 9 CO9 OCH2CH2COOH

3-Benzoyloxypropionic acid

The trivial name acetoxy is retained for the CH3 9CO9O 9 group. Compounds of the type R2C(OR2)3 are named as R2 esters of the hypothetical ortho acids. For example, CH3C(OCH3 )3 is trimethyl orthoacetate. 1.1.3.24 Silicon Compounds. SiH4 is called silane; its acyclic homologs are called disilane, trisilane, and so on, according to the number of silicon atoms present. The chain is numbered from one end to the other so as to give the lowest-numbered locant in radicals to the free valence or to substituents on a chain. The abbreviated form silyl is used for the radical SiH3 9. Numbering and citation of side chains proceed according to the principles set forth for hydrocarbon chains. Cyclic nonaromatic structures are designated by the prefix cyclo-. When a chain or ring system is composed entirely of alternating silicon and oxygen atoms, the parent name siloxane is used with a multiplying affix to denote the number of silicon atoms present. The parent name silazane implies alternating silicon and nitrogen atoms; multiplying affixes denote the number of silicon atoms present. The prefix sila- designates replacement of carbon by silicon in replacement nomenclature. Prefix names for radicals are formed analogously to those for the corresponding carbon-containing compounds. Thus silyl is used for SiH3 9, silyene for 9SiH2 9, silylidyne for 9SiH⬍, as well as trily, tetrayl, and so on for free valences(s) on ring structures. 1.1.3.25 Sulfur Compounds Bivalent Sulfur. The prefix thio, placed before an affix that denotes the oxygen-containing group or an oxygen atom, implies the replacement of that oxygen by sulfur. Thus the suffix -thiol denotes 9SH, -thione denotes 9 (C) "S and implies the presence of an "S at a nonterminal carbon atom, -thioic acid denotes [(C)"S]OH L [(C) " O]SH (that is, the O-substituted acid and the S-substi-

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tuted acid, respectively), -dithioc acid denotes [9 C(S)]SH, and -thial denotes 9(C)HS (or -carbothialdehyde denotes 9CHS). When -carboxylic acid has been used for acids, the sulfur analog is named -carbothioic acid or -carbodithioic acid. Prefixes for the groups HS9 and RS9 are mercapto- and alkylthio-, respectively; this latter name may require parentheses for distinction from the use of thio- for replacement of oxygen in a trivially named acid. Examples of this problem are 4-C2H5 9C6H4 9CSOH named pethyl(thio)benzoic acid and 4-C2H5 9S9 C6H4 9COOH named p-(ethylthio)benzoic acid. When 9 SH is not the principal group, the prefix mercapto- is placed before the name of the parent compound to denote an unsubstituted 9SH group. The prefix thioxo- is used for naming "S in a thioketone. Sulfur analogs of acetals are named as alkylthio- or arylthio-. For example, CH3CH(SCH3 )OCH3 is 1-methoxy-1-(methylthio)ethane. Prefix forms for -carbothioic acids are hydroxy(thiocarbonyl)- when referring to the O-substituted acid and mercapto(carbonyl)- for the S-substituted acid. Salts are formed as with oxygen-containing compounds. For example, C2H5 9S9 Na is named either sodium ethanethiolate or sodium ethyl sulfide. If mercapto- has been used as a prefix, the salt is named by use of the prefix sulfido- for 9S⫺. Compounds of the type R1 9S9R2 are named alkylthio- (or arylthio-) as a prefix to the name of R1 or R2, whichever is the senior. Sulfonium Compounds. Sulfonium compounds of the type R1R2R3S⫹X⫺ are named by citing in alphabetical order the radical names followed by -sulfonium and the name of the anion. For heterocyclic compounds, -ium is added to the name of the ring system. Replacement of ⬎CH by sulfonium sulfur is denoted by the prefix thionia-, and the name of the anion is added at the end. Organosulfur Halides. When sulfur is directly linked only to an organic radical and to a halogen atom, the radical name is attached to the word sulfur and the name(s) and number of the halide(s) are stated as a separate word. Alternatively, the name can be formed from R9SOH, a sulfenic acid whose radical prefix is sulfenyl-. For example, CH3CH2 9 S9Br would be named either ethylsulfur monobromide or ethanesulfenyl bromide. When another principal group is present, a composite prefix is formed from the number and substitutive name(s) of the halogen atoms in front of the syllable thio. For example, BrS9COOH is (bromothio)formic acid. Sulfoxides. Sulfoxides, R1 9SO9 R2, are named by placing the names of the radicals in alphabetical order before the word sulfoxide. Alternatively, the less senior radical is named followed by sulfinyl- and concluded by the name of the senior group. For example, CH3CH2 9 SO9CH2CH2CH3 is named either ethyl propyl sulfoxide or 1-(ethylsulfinyl)propane. When an ⬎SO group is incorporated in a ring, the compound is named an oxide. Sulfones. Sulfones, R1 9SO2 9R2, are named in an analogous manner to sulfoxides, using the word sulfone in place of sulfoxide. In prefixes, the less senior radical is followed by -sulfonyl-. When the ⬎SO2 group is incorporated in a ring, the compound is named as a dioxide. Sulfur Acids. Organic oxy acids of sulfur, that is, 9 SO3H, 9 SO2H, and 9SOH, are named sulfonic acid, sulfinic acid, and sulfenic acid, respectively. In subordinate use, the respective prefixes are sulfo-, sulfino, and sulfeno-. The grouping 9SO2 9 O 9 SO2 9 or 9SO9O 9 SO is named sulfonic or sulfinic anhydride, respectively. Inorganic nomenclature is employed in naming sulfur acids and their derivatives in which sulfur is linked only through oxygen to the organic radical. For example, (C2H5O)2SO2 is diethyl sulfate and C2H5O 9SO2 9 OH is ethyl hydrogen sulfate. Prefixes O- and S- are used where necessary to denote attachment to oxygen and to sulfur, respectively, in sulfur replacement compounds. For example, CH3 9S9SO2 9ONa is sodium S-methyl thiosulfate. When sulfur is linked only through nitrogen, or through nitrogen and oxygen, to the organic radical, naming is as follows: (1) N-substituted amides are designated as N-substituted derivatives of the sulfur amides and (2) compounds of the type R9NH 9SO3H may be named as N-substituted

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sulfamic acids or by the prefix sulfoamino- to denote the group HO3S9NH 9. The groups 9N"SO and 9 N "SO2 are named sulfinylamines and sulfonylamines, respectively. Sultones and Sultams. Compounds containing the group 9SO2 9 O 9 as part of the ring are called -sultone. The 9 SO2 9 group has priority over the 9O 9 group for lowest-numbered locant. Similarly, the 9 SO2 9 N " group as part of a ring is named by adding -sultam to the name of the hydrocarbon with the same number of carbon atoms. The 9SO2 9 has priority over 9N " for lowest-numbered locant.

1.1.4

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Stereochemistry

Concepts in stereochemistry, that is, chemistry in three-dimensional space, are in the process of rapid expansion. This section will deal with only the main principles. The compounds discussed will be those that have identical molecular formulas but differ in the arrangement of their atoms in space. Stereoisomers is the name applied to these compounds. Stereoisomers can be grouped into three categories: (1) Conformational isomers differ from each other only in the way their atoms are oriented in space, but can be converted into one another by rotation about sigma bonds. (2) Geometric isomers are compounds in which rotation about a double bond is restricted. (3) Configurational isomers differ from one another only in configuration about a chiral center, axis, or plane. In subsequent structural representations, a broken line denotes a bond projecting behind the plane of the paper and a wedge denotes a bond projecting in front of the plane of the paper. A line of normal thickness denotes a bond lying essentially in the plane of the paper. 1.1.4.1 Conformational Isomers. A molecule in a conformation into which its atoms return spontaneously after small displacements is termed a conformer. Different arrangements of atoms that can be converted into one another by rotation about single bonds are called conformational isomers (see Fig. 1.1). A pair of conformational isomers can be but do not have to be mirror images of each other. When they are not mirror images, they are called diastereomers.

FIGURE 1.1 Conformations of ethane. (a) Eclipsed; (b) staggered.

Acyclic Compounds. Different conformations of acyclic compounds are best viewed by construction of ball-and-stick molecules or by use of Newman projections (see Fig. 1.2). Both types of representations are shown for ethane. Atoms or groups that are attached at opposite ends of a single bond should be viewed along the bond axis. If two atoms or groups attached at opposite ends of the bond appear one directly behind the other, these atoms or groups are described as eclipsed. That portion of the molecule is described as being in the eclipsed conformation. If not eclipsed, the atoms

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FIGURE 1.2 Newman projections for ethane. (a) Staggered; (b) eclipsed.

or groups and the conformation may be described as staggered. Newman projections show these conformations clearly. Certain physical properties show that rotation about the single bond is not quite free. For ethane there is an energy barrier of about 3 kcal · mol⫺1 (12 kJ · mol⫺1 ). The potential energy of the molecule is at a minimum for the staggered conformation, increases with rotation, and reaches a maximum at the eclipsed conformation. The energy required to rotate the atoms or groups about the carboncarbon bond is called torsional energy. Torsional strain is the cause of the relative instability of the eclipsed conformation or any intermediate skew conformations. In butane, with a methyl group replacing one hydrogen on each carbon of ethane, there are several different staggered conformations (see Fig. 1.3). There is the anti-conformation in which the methyl groups are as far apart as they can be (dihedral angle of 180⬚). There are two gauche conformations in which the methyl groups are only 60⬚ apart; these are two nonsuperimposable mirror images of each other. The anti-conformation is more stable than the gauche by about 0.9 kcal · mol⫺1 (4 kJ · mol⫺1 ). Both are free of torsional strain. However, in a gauche conformation the methyl groups are closer together than the sum of their van der Waals’ radii. Under these conditions van der Waals’ forces are repulsive and raise the energy of conformation. This strain can affect not only the relative stabilities of various staggered conformations but also the heights of the energy barriers

FIGURE 1.3 Conformations of butane. (a) Anti-staggered; (b) eclipsed; (c) gauche-staggered; (d) eclipsed; (e) gauche-staggered; ( f ) eclipsed. (Eclipsed conformations are slightly staggered for convenience in drawing; actually they are superimposed.)

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between them. The energy maximum (estimated at 4.8 to 6.1 kcal · mol⫺1 or 20 to 25 kJ · mol⫺1 ) is reached when two methyl groups swing past each other (the eclipsed conformation) rather than past hydrogen atoms. Cyclic Compounds. Although cyclic aliphatic compounds are often drawn as if they were planar geometric figures (a triangle for cyclopropane, a square for cyclobutane, and so on), their structures are not that simple. Cyclopropane does possess the maximum angle strain if one considers the difference between a tetrahedral angle (109.5⬚) and the 60⬚ angle of the cyclopropane structure. Nevertheless the cyclopropane structure is thermally quite stable. The highest electron density of the carbon-carbon bonds does not lie along the lines connecting the carbon atoms. Bonding electrons lie principally outside the triangular internuclear lines and result in what is known as bent bonds (see Fig. 1.4). Cyclobutane has less angle strain than cyclopropane (only 19.5⬚). It is also believed to have some bent-bond character associated with the carbon-carbon bonds. The molecule exists in a nonplanar conformation in order to minimize hydrogen-hydrogen eclipsing strain. Cyclopentane is nonplanar, with a structure that resembles an envelope (see Fig. 1.5). Four of the carbon atoms are in one plane, and the fifth is out of that plane. The molecule is in continual motion so that the out-of-plane carbon moves rapidly around the ring. The 12 hydrogen atoms of cyclohexane do not occupy equivalent positions. In the chair conformation six hydrogen atoms are perpendicular to the average plane of the molecule and six are directed outward from the ring, slightly above or below the molecular plane (see Fig. 1.6). Bonds which are perpendicular to the molecular plane are known as axial bonds, and those which extend outward

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FIGURE 1.4 The bent bonds (“tear drops”) of cyclopropane.

FIGURE 1.5 The conformations of cyclopentane.

FIGURE 1.6 The two chair conformations of cyclohexane; a ⫽ axial hydrogen atom and e ⫽ equatorial hydrogen atom.

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from the ring are known as equatorial bonds. The three axial bonds directed upward originate from alternate carbon atoms and are parallel with each other; a similar situation exists for the three axial bonds directed downward. Each equatorial bond is drawn so as to be parallel with the ring carboncarbon bond once removed from the point of attachment to that equatorial bond. At room temperature, cyclohexane is interconverting rapidly between two chair conformations. As one chair form converts to the other, all the equatorial hydrogen atoms become axial and all the axial hydrogens become equatorial. The interconversion is so rapid that all hydrogen atoms on cyclohexane can be considered equivalent. Interconversion is believed to take place by movement of one side of the chair structure to produce the twist boat, and then movement of the other side of the twist boat to give the other chair form. The chair conformation is the most favored structure for cyclohexane. No angle strain is encountered since all bond angles remain tetrahedral. Torsional strain is minimal because all groups are staggered. In the boat conformation of cyclohexane (Fig. 1.7) eclipsing torsional strain is significant, although no angle strain is encountered. Nonbonded interaction between the two hydrogen atoms across the ring from each other (the “flagpole” hydrogens) is unfavorable. The boat conformation is about 6.5 kcal · mol⫺1 (27 kJ · mol⫺1 ) higher in energy than the chair form at 25⬚C.

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FIGURE 1.7 The boat conformation of cyclohexane. a ⫽ axial hydrogen atom and e ⫽ equatorial hydrogen atom.

FIGURE 1.8 Twist-boat conformation of cyclohexane.

A modified boat conformation of cyclohexane, known as the twist boat (Fig. 1.8), or skew boat, has been suggested to minimize torsional and nonbounded interactions. This particular conformation is estimated to be about 1.5 kcal · mol⫺1 (6 kJ · mol⫺1 ) lower in energy than the boat form at room temperature. The medium-size rings (7 to 12 ring atoms) are relatively free of angle strain and can easily take a variety of spatial arrangements. They are not large enough to avoid all nonbonded interactions between atoms. Disubstituted cyclohexanes can exist as cis-trans isomers as well as axial-equatorial conformers. Two isomers are predicted for 1,4-dimethylcyclohexane (see Fig. 1.9). For the trans isomer the diequatorial conformer is the energetically favorable form. Only one cis isomer is observed, since the two conformers of the cis compound are identical. Interconversion takes place between the conformational (equatorial-axial) isomers but not configurational (cis-trans) isomers.

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FIGURE 1.9 Two isomers of 1,4-dimethylcyclohexane. (a) Trans isomer; (b) cis isomer.

FIGURE 1.10 Two isomers of decahydronaphthalene, or bicyclo[4.4.0]decane. (a) Trans isomer; (b) cis isomer.

The bicyclic compound decahydronaphthalene, or bicyclo[4.4.0]decane, has two fused six-membered rings. It exists in cis and trans forms (see Fig. 1.10), as determined by the configurations at the bridgehead carbon atoms. Both cis- and trans-decahydronaphthalene can be constructed with two chair conformations. 1.1.4.2 Geometrical Isomerism. Rotation about a carbon-carbon double bond is restricted because of interaction between the p orbitals which make up the pi bond. Isomerism due to such restricted rotation about a bond is known as geometric isomerism. Parallel overlap of the p orbitals of each carbon atom of the double bond forms the molecular orbital of the pi bond. The relatively large barrier to rotation about the pi bond is estimated to be nearly 63 kcal · mol⫺1 (263 kJ · mol⫺1 ). When two different substituents are attached to each carbon atom of the double bond, cis-trans isomers can exist. In the case of cis-2-butene (Fig. 1.11a), both methyl groups are on the same side of the double bond. The other isomer has the methyl groups on opposite sides and is designated as trans-2-butene (Fig. 1.11b). Their physical properties are quite different. Geometric isomerism can also exist in ring systems; examples were cited in the previous discussion on conformational isomers. For compounds containing only double-bonded atoms, the reference plane contains the doublebonded atoms and is perpendicular to the plane containing these atoms and those directly attached to them. It is customary to draw the formulas so that the reference plane is perpendicular to that of

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FIGURE 1.11 Two isomers of 2-butene. (a) Cis isomer, bp 3.8⬚C, mp ⫺138.9⬚C, dipole moment 0.33 D; (b) trans isomer, bp 0.88⬚C, mp ⫺105.6⬚C, dipole moment 0 D.

the paper. For cyclic compounds the reference plane is that in which the ring skeleton lies or to which it approximates. Cyclic structures are commonly drawn with the ring atoms in the plane of the paper. 1.1.4.3 Sequence Rules for Geometric Isomers and Chiral Compounds. Although cis and trans designations have been used for many years, this approach becomes useless in complex systems. To eliminate confusion when each carbon of a double bond or a chiral center is connected to different groups, the Cahn, Ingold, and Prelog system for designating configuration about a double bond or a chiral center has been adopted by IUPAC. Groups on each carbon atom of the double bond are assigned a first (1) or second (2) priority. Priority is then compared at one carbon relative to the other. When both first priority groups are on the same side of the double bond, the configuration is designated as Z (from the German zusammen, “together”), which was formerly cis. If the first priority groups are on opposite sides of the double bond, the designation is E (from the German entgegen, “in opposition to”), which was formerly trans. (See Fig. 1.12.)

FIGURE 1.12 Configurations designated by priority groups. (a) Z (cis); (b) E (trans).

When a molecule contains more than one double bond, each E or Z prefix has associated with it the lower-numbered locant of the double bond concerned. Thus (see also the rules that follow)

(2E,4Z)-2,4-Hexadienoic acid

When the sequence rules permit alternatives, preference for lower-numbered locants and for inclusion in the principal chain is allotted as follows in the order stated: Z over E groups and cis over trans cyclic groups. If a choice is still not attained, then the lower-numbered locant for such a preferred

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group at the first point of difference is the determining factor. For example,

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(2Z,5E)-2,5-Heptadienedioic acid

Rule 1. Priority is assigned to atoms on the basis of atomic number. Higher priority is assigned to atoms of higher atomic number. If two atoms are isotopes of the same element, the atom of higher mass number has the higher priority. For example, in 2-butene, the carbon atom of each methyl group receives first priority over the hydrogen atom connected to the same carbon atom. Around the asymmetric carbon atom in chloroiodomethanesulfonic acid, the priority sequence is I, Cl, S, H. In 1-bromo-1-deuteroethane, the priority sequence is Cl, C, D, H. Rule 2. When atoms attached directly to a double-bonded carbon have the same priority, the second atoms are considered and so on, if necessary, working outward once again from the double bond or chiral center. For example, in 1-chloro-2-methylbutene, in CH3 the second atoms are H, H, H and in CH2CH3 they are C, H, H. Since carbon has a higher atomic number than hydrogen, the ethyl group has the next highest priority after the chlorine atom.

(Z)-1-Chloro-2-methylbutene

(E)-1-Chloro-2-methylbutene

Rule 3. When groups under consideration have double or triple bonds, the multiple-bonded atom is replaced conceptually by two or three single bonds to that same kind of atom. A A Thus, " A is considered to be equivalent to two A's, or and # A equals A . However, a A A A A real has priority over " A; likewise a real A has priority over # A. Actually, both atoms of A A C9O a multiple bond are duplicated, or triplicated, so that C " O is treated as , that O C C9O O9C N C is and , and C # N is treated as . A phenyl carbon (C) (C) (N) (N) (O) (C) CH becomes 9 C C . Only the double-bonded atoms themselves are duplicated, not the atoms or CH groups attached to them. The duplicated atoms (or phantom atoms) may be considered as carrying atomic number zero. For example, among the groups OH, CHO, CH2OH, and H, the OH group has the highest priority, and the C(O, O, H) of CHO takes priority over the C(O, H, H) of CH2OH. 1.1.4.4 Chirality and Optical Activity. A compound is chiral (the term dissymmetric was formerly used) if it is not superimposable on its mirror image. A chiral compound does not have a plane of symmetry. Each chiral compound possesses one (or more) of three types of chiral element, namely, a chiral center, a chiral axis, or a chiral plane.

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Chiral Center. The chiral center, which is the chiral element most commonly met, is exemplified by an asymmetric carbon with a tetrahedral arrangement of ligands about the carbon. The ligands comprise four different atoms or groups. One “ligand” may be a lone pair of electrons; another, a phantom atom of atomic number zero. This situation is encountered in sulfoxides or with a nitrogen atom. Lactic acid is an example of a molecule with an asymmetric (chiral) carbon. (See Fig. 1.13b.)

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FIGURE 1.13 Asymmetric (chiral) carbon in the lactic acid molecule.

A simpler representation of molecules containing asymmetric carbon atoms is the Fischer projection, which is shown here for the same lactic acid configurations. A Fischer projection involves

drawing a cross and attaching to the four ends the four groups that are attached to the asymmetric carbon atom. The asymmetric carbon atom is understood to be located where the lines cross. The horizontal lines are understood to represent bonds coming toward the viewer out of the plane of the paper. The vertical lines represent bonds going away from the viewer behind the plane of the paper as if the vertical line were the side of a circle. The principal chain is depicted in the vertical direction; the lowest-numbered (locant) chain member is placed at the top position. These formulas may be moved sideways or rotated through 180⬚ in the plane of the paper, but they may not be removed from the plane of the paper (i.e., rotated through 90⬚). In the latter orientation it is essential to use thickened lines (for bonds coming toward the viewer) and dashed lines (for bonds receding from the viewer) to avoid confusion. Enantiomers. Two nonsuperimposable structures that are mirror images of each other are known as enantiomers. Enantiomers are related to each other in the same way that a right hand is related to a left hand. Except for the direction in which they rotate the plane of polarized light, enantiomers are identical in all physical properties. Enantiomers have identical chemical properties except in their reactivity toward optically active reagents. Enantiomers rotate the plane of polarized light in opposite directions but with equal magnitude. If the light is rotated in a clockwise direction, the sample is said to be dextrorotatory and is designed as (⫹). When a sample rotates the plane of polarized light in a counterclockwise direction, it is said to be levorotatory and is designed as (⫺). Use of the designations d and l is discouraged. Specific Rotation. Optical rotation is caused by individual molecules of the optically active compound. The amount of rotation depends upon how many molecules the light beam encounters in passing through the tube. When allowances are made for the length of the tube that contains the sample and the sample concentration, it is found that the amount of rotation, as well as its direction, is a characteristic of each individual optically active compound.

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Specific rotation is the number of degrees of rotation observed if a 1-dm tube is used and the compound being examined is present to the extent of 1 g per 100 mL. The density for a pure liquid replaces the solution concentration. Specific rotation ⫽ [␣] ⫽

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observed rotation (degrees) length (dm) ⫻ (g/100 mL)

The temperature of the measurement is indicated by a superscript and the wavelength of the light employed by a subscript written after the bracket; for example, [␣]20 590 implies that the measurement was made at 20⬚C using 590-nm radiation. Optically Inactive Chiral Compounds. Although chirality is a necessary prerequisite for optical activity, chiral compounds are not necessarily optically active. With an equal mixture of two enantiomers, no net optical rotation is observed. Such a mixture of enantiomers is said to be racemic and is designated as (⫾) and not as dl. Racemic mixtures usually have melting points higher than the melting point of either pure enantiomer. A second type of optically inactive chiral compounds, meso compounds, will be discussed in the next section. Multiple Chiral Centers. The number of stereoisomers increases rapidly with an increase in the number of chiral centers in a molecule. A molecule possessing two chiral atoms should have four optical isomers, that is, four structures consisting of two pairs of enantiomers. However, if a compound has two chiral centers but both centers have the same four substituents attached, the total number of isomers is three rather than four. One isomer of such a compound is not chiral because it is identical with its mirror image; it has an internal mirror plane. This is an example of a diastereomer. The achiral structure is denoted as a meso compound. Diastereomers have different physical and chemical properties from the optically active enantiomers. Recognition of a plane of symmetry is usually the easiest way to detect a meso compound. The stereoisomers of tartaric acid are examples of compounds with multiple chiral centers (see Fig. 1.14), and one of its isomers is a meso compound.

FIGURE 1.14 Isomers of tartaric acid.

When the asymmetric carbon atoms in a chiral compound are part of a ring, the isomerism is more complex than in acyclic compounds. A cyclic compound which has two different asymmetric carbons with different sets of substituent groups attached has a total of 22 ⫽ 4 optical isomers: an enantiometric pair of cis isomers and an enantiometric pair of trans isomers. However, when the two asymmetric centers have the same set of substituent groups attached, the cis isomer is a meso compound and only the trans isomer is chiral. (See Fig. 1.15.) Torsional Asymmetry. Rotation about single bonds of most acyclic compounds is relatively free at ordinary temperatures. There are, however, some examples of compounds in which nonbonded

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FIGURE 1.15 Isomers of cyclopropane-1,2-dicarboxylic acid. (a) Trans isomer; (b) meso isomer.

interactions between large substituent groups inhibit free rotation about a sigma bond. In some cases these compounds can be separated into pairs of enantiomers. A chiral axis is present in chiral biaryl derivatives. When bulky groups are located at the ortho positions of each aromatic ring in biphenyl, free rotation about the single bond connecting the two rings is inhibited because of torsional strain associated with twisting rotation about the central single bond. Interconversion of enantiomers is prevented (see Fig. 1.16). For compounds possessing a chiral axis, the structure can be regarded as an elongated tetrahedron to be viewed along the axis. In deciding upon the absolute configuration it does not matter from which end it is viewed; the nearer pair of ligands receives the first two positions in the order of precedence (see Fig. 1.17). For the meaning of (S), see the discussion under Absolute Configuration on p. 1.49. A chiral plane is exemplified by the plane containing the benzene ring and the bromine and oxygen atoms in the chiral compound shown in Fig. 1.18. Rotation of the benzene ring around the oxygen-to-ring single bonds is inhibited when x is small (although no critical size can be reasonably established).

FIGURE 1.16 Isomers of biphenyl compounds with bulky groups attached at the ortho positions.

FIGURE 1.17 Example of a chiral axis.

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FIGURE 1.18 Example of a chiral plane.

FIGURE 1.19 Viewing angle as a means of designating the absolute configuration of compounds with a chiral axis. (a) (R)-2-Butanol (sequence clockwise); (b) (S)-2-butanol (sequence counterclockwise).

Absolute Configuration. The terms absolute stereochemistry and absolute configuration are used to describe the three-dimensional arrangement of substituents around a chiral element. A general system for designating absolute configuration is based upon the priority system and sequence rules. Each group attached to a chiral center is assigned a number, with number one the highest-priority group. For example, the groups attached to the chiral center of 2-butanol (see Fig. 1.19) are assigned these priorities: 1 for OH, 2 for CH2CH3 , 3 for CH3 , and 4 for H. The molecule is then viewed from the side opposite the group of lowest priority (the hydrogen atom), and the arrangement of the remaining groups is noted. If, in proceeding from the group of highest priority to the group of second priority and thence to the third, the eye travels in a clockwise direction, the configuration is specified R (from the Latin rectus, “right”); if the eye travels in a counterclockwise direction, the configuration is specified S (from the Latin sinister, “left”). The complete name includes both configuration and direction of optical rotation, as for example, (S)-(⫹)-2-butanol. The relative configurations around the chiral centers of many compounds have been established. One optically active compound is converted to another by a sequence of chemical reactions which are stereospecific; that is, each reaction is known to proceed spatially in a specific way. The configuration of one chiral compound can then be related to the configuration of the next in sequence. In order to establish absolute configuration, one must carry out sufficient stereospecific reactions to relate a new compound to another of known absolute configuration. Historically the configuration of D-(⫹)-2,3-dihydroxypropanal has served as the standard to which all configuration has been compared. The absolute configuration assigned to this compound has been confirmed by an X-ray crystallographic technique.

1.1.5 Chemical Abstracts Indexing System When compounds of complex structure are considered, the number of name possibilities grows rapidly. To avoid having index entries for all possible names, Chemical Abstracts Service has developed what might be called the principle of inversion. The indexing system employs inverted

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entries to bring together related compounds in an alphabetically arranged index. The index heading parent from the Chemical Substance Index appears in the Formula Index in lightface before the “comma of inversion.” The substituents follow the “comma of inversion” in alphabetical order. Any name modification appears on a separate line. If necessary, the chemical description is completed by citation of an associated ion, a functional derivative, a “salt with” or “compound with” term, and/or a stereochemical descriptor. Quite naturally there is a certain amount of arbitrariness in this system, although the IUPAC nomenclature is followed. The preferred Chemical Abstracts index names for chemical substances have been, with very few exceptions, continued unchanged (since 1972) as set forth in the Ninth Collective Index Guide and in a journal article.* Any revisions appear in the updated Index Guide; new editions appear at 18-month intervals. Appendix VI is of particular interest to chemists. Reprints of the Appendix may be purchased from Chemical Abstracts Service, Marketing Division, P.O. Box 3012, Columbus, Ohio 43210.

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* J. Chem. Doc. 14(1):3–15 (1974).

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TABLE 1.13 Names and Formulas of Organic Radicals For more comprehensive lists, see the various lists of radicals given in the subject indexes of the annual and decennial indexes of Chemical Abstracts. Name Acenaphthenyl Acenaphthenylene Acenaphthenylidene Acetamido Acetimidoyl Acetoacetyl Acetohydrazonoyl Acetohydroximoyl Acetonyl Acetonylidene Acetoxy Acetyl (not ethanoyl) Acetylamino Acetylhydrazino Acetylimino Acridinyl (from acridine) Acroyloyl (or propenoyl) Adipoyl (or hexanedioyl) Alanyl ␤-Alanyl Allyl (or 2-propenyl) Allylidene Allyloxy Amidino Amino Aminomethyleneamino Aminooxy Ammonio Amyl, see Pentyl Anilino Anisidino (o-, m-, or p-) Anisoyl (o-, m-, or p-; or methoxybenzoyl) Anthraniloyl Anthryl (from anthracene) Anthrylene Arginyl

Asparaginyl Aspartoyl

␣-Aspartyl Atropoyl (or 2-phenylpropenoyl) Azelaoyl, see Nonanedioyl

Formula C12H9 9 9C12H8 9 C12H8 " CH3 9CO9NH9 CH3C("NH)9 CH3 9CO9CH2 9CO9 CH3 9C("NNH2)9 CH3 9C("NOH)9 CH3 9CO9CH2 9 CH3 9CO9CH" CH3 9CO9O9 CH3 9CO9 CH3 9CO9NH9 CH3 9CO9NH9NH9 CH3 9CO9N" NC13H8 9 CH2 "CH9CO9 9CO9[CH2]4 9CO9 CH3 9CH(NH2)9CO9 H2N9CH2 9CH2 9CO9 CH2 "CH9CH2 9 CH2 "CH9CH" CH2 "CH9CH2 9O9 H2N9C("NH)9 H2N9 H2N9CH"N9 H2N9O9 ⫹ H3N9 C6H5 9NH9 CH3O9C6H4 9NH9 CH3O9C6H4 9CO9

o-NH2 9C6H4 9CO9 C14H9 9 9C14H8 9 H2N9C("NH)9NH9 [CH2]3 9CH(NH)9 CO9 H2N9CO9CH2 9 CH(NH2)9CO9 9CO9CH2 9 CH(NH2)9CO9 HO2C9CH2CH(NH2)9 C6H5 9C("CH2)9CO9

Name Azido Azino Azo Azoxy Azulenyl Benzamido Benzeneazo Benzeneazoxy 1,2-Benzenedicarbonyl, see Phthaloyl 1,3-Benzenedicarbonyl (or isophthaloyl) 1,4-Benzenedicarbonyl (or terephthaloyl) Benzenesulfinyl Benzenesulfonamido Benzenesulfonyl Benzenesulfonylamino Benzenetriyl Benzhydryl (or diphenylmethyl) Benzidino Benziloyl (or 2-hydroxy2,2-diphenylethanoyl) Benzimidazolyl Benzimidoyl Benzofuranyl Benzopyranyl Benzoquinonyl (1,2- or 1,4-) Benzo[b]thienyl Benzoyl Benzoylamino Benzoylhydrazino Benzoylimino Benzoyloxy Benzyl Benzylidene Benzylidyne Benzyloxy Benzyloxycarbonyl Benzylthio Biphenylenyl Biphenylyl Bornenyl Bornyl (not camphyl or bornylyl) Bromo Bromoformyl

Formula N3 9 "N9N" 9N"N9 9N(O)9N9 C10H7 9 C6H5 9CO9NH9 C6H5 9N"N9 C6H5 9N2O9

9CO9C6H4 9CO9 (m-) 9CO9C6H4 9CO9 (p-) C6H5 9SO9 C6H5 9SO2 9NH9 C6H5 9SO2 9 C6H5 9SO2 9NH9 C6H3 9 (C6H5)2CH9 p-H2N9C6H4 9C6H4 9 NH9 (C6H5)2C(OH)9CO9 N2C7H5 9 C6H5 9C("NH)9 OC8H5 9 OC9H7 9 (O")2C6H3 9 SC8H5 9 C6H5 9CO9 C6H5 9CO9NH9 C6H5 9CO9NH9NH9 C6H5 9CO9N" C6H5 9CO9O9 C6H5 9CH2 9 C6H5 9CH" C6H5 9C# C6H5 9CH2 9O9 C6H5 9CH2 9O9CO9 C6H5 9CH2 9S9 C12H7 9 C6H5 9C6H4 9 C10H15 9 C10H17 9 Br9 Br9CO9

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TABLE 1.13 Names and Formulas of Organic Radicals (Continued) Name Bromonio Butadienyl (1,3- shown) Butanedioyl, see Succinyl Butanediylidene Butanediylidyne Butanoyl, see Butyryl cis-Butenedioyl, see Maleoyl trans-Butenedioyl, see Fumaroyl Butenoyl, see Crotonoyl and Isocrotonoyl 1-Butenyl 2-Butenyl (not crotyl) 2-Butenylene Butenylidene (2- shown) Butenylidyne (2- shown) Butoxy sec-Butoxy (unsubstituted only) tert-Butoxy (unsubstituted only) Butyl sec-Butyl (unsubstituted only) tert-Butyl (unsubstituted only) Butylidene sec-Butylidene (unsubstituted only) Butylidyne Butyryl (or butanoyl) Camphoroyl Carbamoyl Carbazolyl Carbazoyl Carbonimidoyl Carbonohydrazido (preferred to carbohydazido or carbazido) Carbonyl Carbonyldioxy Carboxy Carboxylato Chloro Chlorocarbonyl, see Chloroformyl Chloroformyl Chlorosyl Chlorothio Chloryl

Formula ⫹

HBr9 CH2 "CH9CH"CH9 "CH9CH2 9CH2 9 CH" #C9CH2 9CH2 9C#

CH3 9CH2 9CH"CH9 CH3 9CH"CH9CH2 9 9CH2 9CH"CH9 CH2 9 CH3CH"CH9CH" CH3 9CH"CH9C# CH3 9[CH2]3 9O9 C2H5 9CH(CH3)9O9 (CH3)3C9O9 CH3 9[CH2]3 9 or C4H9 9 C2H5 9CH(CH3)9 (CH3)3C9 CH3 9CH2 9CH2 9CH" C2H5C(CH3)"

Name Cinnamoyl (or 3-phenylpropenoyl) Cinnamyl Cinnamylidene Citraconoyl (unsubstituted only) Crotonoyl

Formula C6H5 9CH"CH9CO C6H5 9CH"CH9CH2 9 C6H5 9CH"CH9CH" HC 9 CO 9 CH3 9 C9 CO 9 CH3 9CH"CH9CO9 (trans)

Crotyl, see 2-Butenyl Cumenyl (o-, m-, or p-) Cyanato Cyano Cyclobutyl Cycloheptyl Cyclohexadienyl (2,4shown)

(CH3)2CH9C6H4 9 NCO9 NC9 C4H7 9 C7H13 9 CH " CH 9 CH 9

Cyclohexadienylidene (2,4- shown)

CH 9 CH2 9 C

Cyclohexanecarbonyl Cyclohexanecarbothioyl Cyclohexanecarboxamido Cyclohexanecarboximidoyl Cyclohexenyl 2-Cyclohexenylidene

CH 9 CH CH C6H11 9CO9 C6H11 9CS9 C6H11 9CO9NH9 C6H11 9C("NH)9 C6H9 9 CH " CH 9 C

Cyclohexyl Cyclohexylcarbonyl Cyclohexylene Cyclohexylidene

CH " CH 9 CH2

CH2 H2C 9 CH2 C6H11 9 C6H11 9CO9 9C6H10 9 CH2 9 CH2 9 C CH2 9 CH2 9 CH2

CH3 9[CH2]2 9C# CH3 9CH2 9CH2 9CO9 C10H14O2 9 H2N9CO9 NC12H8 9 H2N9NH9CO9 9C("NH)9 H2N9NH9CO9NH9 NH9 9CO9 or "C(O) 9O9CO9O9 HO2C9 9O2C9 Cl9

Cl9C(O)9 OCl9 ClS9 O2Cl9

Cyclohexylthiocarbonyl Cyclopentadienyl Cyclopentadienylidene Cyclopenta[a]phenanthryl 1,2-Cyclopentenophenanthryl Cyclopentenyl Cyclopentyl Cyclopentylene Cyclopropyl Cysteinyl Cystyl

Decanedioyl Decanoyl Decyl Diacetoxyiodo Diacetylamino Diaminomethyleneamino

C6H11 9CS9 C5H5 9 CH"CH9CH"CH9C" C17H17 9 C17H11 9 C5H7 9 C5H9 9 9C5H8 9 C3H5 9 HS9CH2 9CH(NH2)9 CO9 9CO9CH(NH2)9 CH2 9S9S9CH2 9 CH(NH2)9CO9 9CO9[CH2]8 9CO9 CH3 9[CH2]8 9CO9 CH3 9[CH2]9 9 (CH3 9CO9O)2I9 (CH3 9CO)2N9 (NH2)2C"N9

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TABLE 1.13 Names and Formulas of Organic Radicals (Continued) Name Diazo Diazoamino Dibenzoylamino Dichloroiodo Diethylamino 3,4-Dihydroxybenzoyl, see Protocatechuoyl 2,3-Dihydroxybutanedioyl, see Tartaroyl Dihydroxyiodo 2,3-Dihydroxypropanoyl, see Glyceroyl 3,4-Dimethoxybenzoyl, see Veratroyl 3,4-Dimethoxyphenethyl 3,4-Dimethoxyphenylacetyl Dimethylamino Dimethylbenzoyl Dioxy Diphenylamino Diphenylmethylene Dithio Diethiocarboxy Dithiosulfo Dodecanoyl Dodecyl Elaidoyl (or trans-9-octadecenoyl) Epidioxy (as a bridge) Epidiseleno (as bridge) Epidithio (as a bridge) Epimino (as a bridge) Episeleno (as a bridge) Epithio (as a bridge) Epoxy (as a bridge) Ethanesulfonamide Ethanoyl, see Acetyl Ethenyl, see Vinyl Ethoxalyl Ethoxy Ethoxycarbonyl Ethyl Ethylamino Ethylene Ethylenedioxy Ethylidene Ethylidyne Ethylsulfonylamino Ethylthio Ethynyl Ethynylene Fluoranthenyl

Formula "N2 9N"N9NH9 (C6H5 9CO)2N9 Cl2I9 (C2H5)2N9

(HO)2I9

3,4(CH3O)2C6H3CH2CH9 3,4(CH3O)2C6H3CH2CO9 (CH3)2N9 (CH3)2C6H6H3 9CO9 9O9O9 (C6H5)2N9 (C6H5)2C" 9S9S9 HSSC9 HOS2 9 CH3[CH2]10 9CO9 CH3[CH2]11 9 CH3[CH2]7CH"CH9 [CH2]7 9CO9 9O9O9 9Se9Se9 9S9S9 9NH9 9Se9 9S9 9O9 C2H5 9SO2 9NH9

C2H5 9OOC9CO9 C2H5 9O9 C2H5 9O9CO9 C2H5 9 or CH3 9CH2 9 C2H5 9NH9 9CH2 9CH2 9 9O9CH2 9CH2 9O9 CH3 9CH" CH3 9C# C2H5 9SO2 9NH9 C2H5 9S9 HC#C9 9C#C9 C16H9 9

Name

Formula

Fluorenyl Fluoro Fluoroformyl Formamido Formimidoyl Formyl (not methanoyl) Formylamino Formylimino Formyloxy Fumaroyl (or trans-butenedioyl) Furancarbonyl, see Furoyl

C13H9 9 F9 F9CO9 OCH9NH9 CH("NH)9 OCH9 or 9C(O)H H9CO9NH9 H9CO9N" H9CO9O9 9CO9CH"CH9CO9 (trans)

Furfuryl (2- only; preferred to 2-furylmethyl)

HC

Furfurylidene (2- only)

HC

Furoyl (3- shown; preferred to furancarbonyl) Furyl 3-Furylmethyl

Galloyl (or 3,4,5-trihydroxybenzoyl) Geranyl (from geraniol) Glutaminyl Glutamoyl

␣-Glutamyl ␥-Glutamyl Glutaryl (or pentanedioyl) Glyceroyl (or 2,3- dihydroxypropanoyl) Glycoloyl (or hydroxyethanoyl) Glycyl Glycylamino Glyoxyloyl Guanidino Guanyl, see Amidino Heptanamido Heptanedioyl Heptanoyl Heptyl Hexadecanoyl Hexadecyl Hexamethylene Hexanamido Hexanedioyl (or adipoyl)

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CH " C 9 CH2 9 CH 9 O CH " C 9 CH CH 9 O CH " C 9 CO 9

O CH " CH OC4H3 9 CH " C 9 CH2 9 O CH " CH 3,4,5-(HO)3C6H2 9 CO 9 C10H17 9 H2N9CO9CH2 9CH2 9 CH(NH2)9CO9 9CO9CH2 9CH2 9 CH(NH2)9CO9 HOOC[CH2]2CH(NH2)9 CO9 HOOC9CH(NH2)9 [CH2]2 9CO9 9CO9[CH2]3 9CO9 HO9CH2 9CH(OH)9 CO9 HO9CH2 9CO9 H2N9CH2 9CO9 H2N9CH2 9CO9NH9 OHC9CO9 H2N9C("NH)9NH9 CH3 9[CH2]5 9CO9NH9 9CO9[CH2]5 9CO9 CH3 9[CH2]5 9CO9 CH3 9[CH2]5 9CH2 9 CH3 9[CH2]14 9CO9 CH3 9[CH2]14 9CH2 9 9[CH2]6 9 CH3 9[CH2]4 9CO9NH9 9CO9[CH2]4 9CO9

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TABLE 1.13 Names and Formulas of Organic Radicals (Continued) Name Hexanimidoyl Hexanoyl Hexanoylamino Hexyl Hexylidene Hexyloxy Hippuroyl Histidyl Homocysteinyl Homoseryl Hydantoyl Hydratropoyl (or 2-phenylpropanoyl) Hydrazi Hydrazino Hydrazo Hydrazono Hydroperoxy Hydroseleno Hydroxy Hydroxyamino o-Hydroxybenzoyl (or salicyloyl) m-Hydroxybenzoyl p-Hydroxybenzoyl Hydroxybutanedioyl, see Maloyl 2-Hydroxy-2,2-diphenyl ethanoyl, see Benziloyl Hydroxyethanoyl, see Glycoloyl Hydroxyimino 4-Hydroxy-3-methoxybenzoyl (or vanilloyl) 3-Hydroxy-2-phenylpropanoyl (or tropoyl) Hydroxypropanedioyl (or tartronoyl) 2-Hydroxypropanoyl (or lactoyl) Icosyl Imino Iminomethylamino Iodo Iodoformyl

Formula

Name

CH3 9[CH2]4 9C("NH)9 CH3 9[CH2]4 9CO9 CH3 9[CH2]4 9CO9NH9 CH3 9[CH2]4 9CH2 9 CH3 9[CH2]4 9CH" CH3[CH2]5 9O9 C6H5 9CO9NH9CH2 9 CO9 N2C3H3 9CH2 9CH(NH2)9 CO9 HS9CH2 9CH2 9 CH(NH2)9CO9 HO9CH2 9CH2 9 CH(NH2)9CO9 H2N9CO9NH9CH2 9 CO9 C6H5 9CH(CH3)9CO9

Iodonio Iodosyl Iodyl Isobutoxy (unsubstituted only) Isobutyl (unsubstituted only) Isobutylidene (unsubstituted only) Isobutylidyne (unsubstituted only) Isobutyryl (unsubstituted only; or 2-methylpropanoyl) Isocarbonohydrazido

9NH9NH9 (to single atom) H2N9NH9 9NH9NH9 (to different atoms) H2N9N" HO9O9 HSe9 HO9 HO9NH9 o-HO9C6H4 9CO9

Isocyanato Isocyano Isohexyl (unsubstituted only) Isoleucyl

m-HO9C6H4 9CO9 p-HO9C6H4 9CO9

HO9N" 4-HO,3-CH3O9 C6H3 9CO9 C6H5 9CH(CH2OH)9CO9

Isocrotonoyl

Isonicotinoyl (or 4-pyridinecarbonyl) Isopentyl (unsubstituted only) Isophthaloyl (or 1,3benzenedicarbonyl) Isopropenyl (unsubstituted only; or 1-methylvinyl) Isopropoxy (unsubstituted only) Isopropyl (unsubstituted only) p-Isopropylbenzoyl Isopropylbenzyl Isopropylidene Isoselenocyanato Isosemicarbazido Isothiocyanato Isothioureido

9CO9CH(OH)9CO9 Isoureido CH3 9CH(OH)9CO9 CH3 9[CH2]18 9CH2 9 9NH9, HN" HN"CH9NH9 I9 I9CO9

Isovaleryl (unsubstituted only; or 3-methylbutanoyl) Lactoyl Lauroyl (unsubstituted only)

Formula ⫹ HI9 OI9 O2I9 (CH3)2CH9CH2 9O9

(CH3)2CH9CH2 9 (CH3)2CH9CH" (CH3)2CH9C# (CH3)2CH9CO9

H2N9N"C(OH)9NH9 NH9 CH3 9CH"CH9CO9 (cis) OCN9 CN9 (CH3)2CH9[CH2]3 9 C2H5 9CH(CH3)9 CH(NH2)9CO NC5H4 9CO9 (4-) (CH3)2CH9CH2 9CH2 9 9CO9C6H4 9CO9 (m-) CH2 "C(CH3)9 (CH3)2CH9O9 (CH3)2CH9 p-(CH3)2CH9C6H4 9CO9 (CH3)2CH9C6H4 9CH2 9 (CH3)2C" SeCN9 H2N9NH9C(OH)"N9 SCN9 HN"C(SH)9NH9, H2N9C(SH)"N9 HN"C(OH)9NH9, H2N9C(OH)"N9 (CH3)2CH9CH2 9CO9

CH3 9CH(OH)9CO9 CH3 9[CH2]10 9CO9

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TABLE 1.13 Names and Formulas of Organic Radicals (Continued) Name Leucyl Lysyl Maleoyl Malonyl Maloyl MercaptoMesaconoyl (unsubstituted only) Mesityl Mesoxalo Mesoxalyl Mesyl Methacryloyl (or 2-methylpropenoyl) Methaneazo Methaneazoxy Methanesulfinamido Methanesulfinyl Methanesulfonamido Methanesulfonyl, see Mesyl Methanoyl, see Formyl Methionyl

Formula (CH3)2CH9CH2 9 CH(NH2)9CO9 H2N9[CH2]4 9 CH(NH2)9CO9 9CO9CH"CH9CO9 9CO9CH2 9CO9 9CO9CH(OH)9CH2 9 CO9 HS9 9 CO 9 CH CH3 9 C 9 CO 9 2,4,6-(CH3)3C6H2 9 HOOC9CO9CO9 9CO9CO9CO9 CH3 9SO2 9 CH2 "C(CH3)9CO9 CH3 9N"N9 CH3 9N2O9 CH3 9SO9NH9 CH3 9SO9 CH3 9SO2 9NH9

CH3 9S9CH2 9CH2 9 CH(NH2)9CO9 CH3OOC9CO9 CH3O9 CH3O9C6H4 9CO9

Methoxalyl Methoxy Methoxybenzoyl (o-, m-, or p-) Methoxycarbonyl Methoxyimino Methoxyphenyl Methoxysulfinyl Methoxysulfonyl Methoxy(thiosulfonyl) Methyl Methylallyl Methylamino Methylazo Methylazoxy ␣-Methylbenzyl Methylbenzyl 3-Methylbutanoyl cis-Methylbutenedioyl

CH3O9CO9 CH3O9N" CH3O9C6H4 9 CH3O9SO9 CH3O9SO2 9 CH3O9S2O9 CH3 9 CH2 "C(CH3)9CH2 9 CH3 9NH9 CH3 9N"N9 CH3 9N2O9 C6H5 9CH(CH3)9 CH3 9C6H4 9CH2 9 (CH3)2CH9CH2 9CO9 HC 9 CO 9

trans-Methylbutenedioyl

CH3 9 C 9 CO 9 9 CO 9 CH

Methyldithio Methylene Methylenedioxy 3,4-Methylenedioxybenzoyl

CH3 9 C 9 CO 9 CH3 9S9S9 9CH2 9, H2C" 9O9CH2 9O9 3,4-CH2O2 : C6H3 9 CO9

Name 5-Methylhexyl Methylidyne Methylsulfinimidoyl Methylsulfinohydrazonoyl Methylsulfinohydroximoyl Methylsulfinyl Methylsulfinylamino Methylsulfonohydrazonoyl Methylsulfonimidoyl Methylsulfonohydroxamoyl Methylsulfonyl Methylthio (Methylthio)sulfonyl 1-Methylvinyl, see Isopropenyl Morpholino (4- only) Morpholinyl (3- shown)

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Formula (CH3)2CH9[CH2]4 9 HC# CH3 9S("NH)9 CH3 9S("NNH2)9 CH3 9S("N9OH)9 CH3 9SO9 CH3 9SO9NH9 CH3 9S(O)(NNH2)9 CH3 9S(O)("NH)9 CH3 9S(O)(N9OH)9 CH3 9SO2 9 CH3S9 CH3S9SO2 9

O O

CH29 CH2 CH29 CH2 CH29 CH2

N9 NH

CH29 CH Myristoyl (unsubstituted only) Naphthalenazo Naphthalenecarbonyl, see Naphthoyl Naphthoyl Naphthoyloxy Naphthyl Naphthylazo Naphthylene Naphthylenebisazo Naphthyloxy Neopentyl (unsubstituted only) Nicotinoyl Nitrilo Nitro aci-Nitro Nitroso Nonanedioyl Nonanoyl Nonyl Norbornyl Norbornylyl, see Norbornyl Norcamphyl, see Norbornyl Norleucyl Norvalyl Octadecanoyl

CH3 9[CH2]12 9CO9 C10H7 9N"N9

C10H7 9CO9 C10H7 9CO9O9 C10H7 9 C10H7 9N"N9 9C10H6 9 9N"N9C10H6 9 N"N9 C10H7 9O9 (CH3)3C9CH2 9 NC5H4 9CO9 (3-) N# O2N9 HO9(O")N" ON9 9CO9[CH2]7 9CO9 CH3 9[CH2]7 9CO9 CH3 9[CH2]7 9CH2 9 C7H11 9

CH3 9[CH2]3 9CH(NH2)9 CO9 CH3 9CH2 9CH2 9 CH(NH2)9CO9 CH3 9[CH2]16 9CO9

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TABLE 1.13 Names and Formulas of Organic Radicals (Continued) Name cis-9-Octadecenoyl Octadecyl Octanedioyl Octanoyl Octyl Oleoyl Ornithyl Oxalacetyl Oxalaceto Oxalo Oxalyl Oxamoyl Oxido Oxo Oxonio Oxy Palmitoyl (unsubstituted only) Pentafluorothio Pentamethylene Pentanedioyl, see Glutaryl Pentanoyl, see Valeryl Pentenyl (2- shown) Pentyl Pentyloxy Perchloryl Phenacyl Phenacylidene Phenanthryl Phenethyl Phenetidino (o-, m-, or p-) Phenoxy Phenyl Phenylacetyl Phenylazo Phenylazoxy Phenylcarbamoyl Phenylene Phenylenebisazo Phenylimino 2-Phenylpropanoyl 3-Phenylpropenoyl, see Cinnamoyl 3-Phenylpropyl

Formula H[CH2]8 9CH"CH9 [CH2]7 9CO9 CH3 9[CH2]16 9CH2 9 9CO9[CH2]6 9CO9 CH3 9[CH2]6 9CO9 CH3 9[CH2]6 9CH2 9 H[CH2]8 9CH"CH9 [CH2]7 9CO9 H2N9[CH2]3 9 CH(NH2)9CO9 9CO9CH2 9CO9 CO9 HOOC9CO9CH2 9 CO9 HOOC9CO9 9CO9CO9 H2N9CO9CO9 ⫺ O9 (ion) O" ⫹ H2O9 9O9 CH3 9[CH2]14 9CO9 F5S9 9CH2 9CH2 9CH2 9 CH2 9CH2 9

CH3 9CH2 9CH"CH9 CH2 9 CH3 9CH2 9CH2 9CH2 9 CH2 9 CH3 9[CH2]4 9O9 O3Cl9 C6H5 9CO9CH2 9 C6H5 9CO9CH" C14H9 9 C6H5 9CH2 9CH2 9 C2H5O9C6H4 9NH9 C6H5 9O9 C6H5 9 C6H5 9CH2 9CO9 C6H5 9N"N9 C6H5 9N2O9 C6H5 9NH9CO 9C6H4 9 9N"N9C6H4 9 N"N9 C6H5 9N" C6H5 9CH(CH3)9CO9

C6H5 9CH2 9CH2 9 CH2 9

Name

Formula

Phthalidyl

C6H5 9NH9SO2 C6H5 9SO9 C6H5 9SO2 9 C6H5 9SO2 9NH9 C6H5 9S9 C6H5 9NH9CO9NH9 H2N 9 CO 9 C6H4 9 CO 9 (o-) C6H4 9 CO 9 O 9 CH 9

Phthalimido

CO 9 C6H4 9 CO 9 N 9

Phthaloyl Picryl Pimeloyl (unsubstituted only) Piperidino (1- only) Piperidyl (2-, 3-, 4-) Piperonyl Pivaloyl (unsubstituted only) Polythio Propanedioyl, see Malonyl Propanoyl, see Propionyl Propargyl, see 2-Propynyl Propenoyl, see Acryloyl 1-Propenyl 2-Propenyl, see Allyl Propenylene Propioloyl Propionamido Propionyl Propionylamino Propionyloxy Propoxy Propyl Propylene Propylidene Propylidyne Propynoyl, see Propiolyl 1-Propynyl 2-Propynyl Protocatechuoyl 3-Pyridinecarbonyl 4-Pyridinecarbonyl Pyridinio Pyridyl 2-Pyridylcarbonyl Pyridyloxy Pyruvoyl Salicyl Salicylidene Salicyloyl Sarcosyl

9CO9C6H4 9CO9 (o-) 2,4,6-(NO2)3C6H2 9 9CO9[CH2]5 9CO9

Phenylsulfamoyl Phenylsulfinyl Phenylsulfonyl Phenylsulfonylamino Phenylthio 3-Phenylureido Phthalamoyl

C5H10N9 NC5H10 9 3,4-CH2O2 : C6H3 9CH2 9 (CH3)3C9CO9 9S4 9

CH3 9CH"CH9 9CH2 9CH"CH9 CH#C9CO9 CH3 9CH2 9CO9NH9 CH3 9CH2 9CO9 CH3 9CH2 9CO9NH9 CH3 9CH2 9CO9O9 CH3 9CH2 9CH2 9O CH3 9CH2 9CH2 9 9CH(CH3)9CH2 9 CH3 9CH2 9CH" CH3 9CH2 9C# CH3 9C#C9 HC#C9CH2 9 3,4-(HO)2C6H3 9CO9 NC5H4 9CO9 (3-) NC5H4 9CO9 (4-) ⫹ NC5H5 9 (ion) NC5H4 9 NC5H4 9CO9 (2-) NC5H4 9O9 CH3 9CO9CO9 o-HO9C6H4 9CH2 9 o-HO9C6H4 9CH" o-HO9C6H4 9CO9 CH3 9NH9CH2 9CO9

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TABLE 1.13 Names and Formulas of Organic Radicals (Continued) Name Sebacoyl (unsubstituted only) Seleneno Selenino Seleninyl Seleno Selenocyanato Selenoformyl Selenonio Selenono Selenonyl Selenoureido Selenoxo Semicarbazido Semicarbazono Seryl Stearoyl (unsubstituted only) Styryl Suberoyl (unsubstituted only) Succinamoyl

Succinimido

Succinimidoyl Succinyl Sulfamoyl Sulfanilamido Sulfanilyl Sulfenamoyl Sulfeno Sulfido Sulfinamoyl Sulfino Sulfinyl Sulfo Sulfoamino Sulfonato Sulfonio Sulfonyl Sulfonyldioxy Tartaroyl Tartronoyl Tauryl Telluro Terephthaloyl Terphenylyl

Formula 9CO9[CH2]8 9CO9 HOSe9 HO2Se9 OSe" 9Se9 NC9Se9 HSeC9 ⫹ H2Se9 (ion) HO3Se9 O2Se9 H2N9CSe9NH9 (C)"Se H2N9CO9NH9NH9 H2N9CO9NH9N" HO9CH2 9CH(NH2)9 CO9 CH3 9[CH2]16 9CO9 C6H5 9CH"CH9 9CO9[CH2]6 9CO9 H2N9CO9CH2 9CH2 9 CO9 O CH2 9 C N9 CH2 9 C O 9C("NH)9CH2 9 CH2C("NH)9 9CO9CH2 9CH2 9CO9 H2N9SO2 9 p-H2N9C6H4 9SO2 9 NH9 p-H2N9C6H4 9SO2 9 H2N9S9 HO9S9 ⫺ S9 (ion) H2N9SO9 HO2S9 9SO9 HO9SO2 9 HO2S9NH9 ⫺ O3S9 (ion) ⫹ H2S9 (ion) 9SO2 9 9O9SO2 9O9 9CO9CH(OH)9 CH(OH)9CO9 9CO9CH(OH)9CO9 H2N9CH2 9CH2 9SO2 9 Te replacing O 9CO9C6H4 9CO9 (p-) C6H5 9C6H4 9C6H4 9

Name (Terthiophen)yl Tetradecanoyl Tetradecyl Tetramethylene

Thenoyl (2- shown) Thenyl Thienyl Thio Thioacetyl Thiobenzoyl Thiocarbamoyl Thiocarbazono Thiocarbodiazono Thiocarbonohydrazido Thiocarbonyl Thiocarboxy Thiocyanato Thioformyl Thiophenecarbonyl, see Thenoyl Thiosemicarbazido Thiosulfino Thiosulfo Thioreido Thioxo Threonyl Toluenesulfonyl (o-, m-) Toluidino (o-, m-, or p-) Toluoyl (o-, m-, or p-) Tolyl (o-, m-, or p-) Tolylsulfonyl Tosyl (p- only) Triazano Triazeno Trichlorothio Tridecanoyl Tridecyl Trifluorothio 3,4,5-Trihydroxybenzoyl Trimethylammonio Trimethylanilino (all isomers) Trimethylene Trimethylenedioxy Triphenylmethyl Trithio Trithiosulfo

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Formula SC4H3 9SC4H2 9SC4H2 9 CH3 9[CH2]12 9CO9 CH3 9[CH2]12 9CH2 9 9CH2 9CH2 9CH2 9 CH2 9 CO 9 CH " C S CH " CH SC4H3 9CH2 9 SC4H3 9 9S9 CH3 9CS9 C6H5 9CS9 H2N9CS9 HN"N9CS9NH9 NH9 HN"N9CS9N"N9 H2N9NH9CS9NH9 NH9 9CS9, SC" HSOC9, HS9CO9 NCS9 SHC9, HCS9

H2N9CS9NH9NH9 HOS2 9 HO2S2 9 H2N9CS9NH9 S" CH3 9CH(OH)9 CH(NH2)9CO9 CH3 9C6H4 9SO2 9 CH3 9C6H4 9NH9 CH3 9C6H4 9CO9 CH3 9C6H4 9 CH3 9C6H4 9SO2 9 p-CH3 9C6H4 9SO2 9 H2N9NH9NH9 H2N9N"N9 Cl3S9 CH3 9[CH2]11 9CO9 CH3 9[CH2]12 9 F3S9 3,4,5-(HO)3C6H2 9CO9 (CH3)3N⫹ 9 (ion) (CH3)3C6H2 9NH9 9CH2 9CH2 9CH2 9 9O9CH2 9CH2 9 CH2 9O9 (C6H5)3C9 9S3 9 HS9S3 9

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TABLE 1.13 Names and Formulas of Organic Radicals (Continued) Name

Formula (C6H5)3C9 C6H5 9CH(CH2OH)9 CO9 p-HO9C6H4 9CH2 9 CH(NH2)9CO9 CH3 9[CH2]9 9CO9 CH3 9[CH2]9 9CH2 9 H2N9CO9NH9 9NH9CO9NH9 CH3 9[CH2]3 9CO9 (CH3)2CH9CH(NH2)9 CO9

Trityl Tropoyl Tyrosyl Undecanoyl Undecyl Ureido Ureylene Valeryl Valyl

1.2

Name

Formula 3,4-CH3O(HO)C6H3 9 CO9 3,4-CH3O(HO)C6H3 9 CH2 9 3,4-(CH3O)2C6H3 9 CO9 3,4-(CH3O)2C6H2 9 CH2 9 CH2 "CH9 9CH"CH9 (CH3)2C6H3 9NH9 (CH3)2C6H3 9

Vanilloyl Vanillyl Veratroyl Veratryl Vinyl Vinylene Xylidino (all isomers) Xylyl (all isomers)

PHYSICAL PROPERTIES OF PURE SUBSTANCES

TABLE 1.14 Empirical Formula Index of Organic Compounds The alphanumeric designations are keyed to Table 1.15. Br2OS: t149 ClHO3S: c248 ClH4NO: h139 Cl2OS: t150 Cl2H2Si: d270a Cl3HSi: t249 Cl3PS: t158 H3NO3S: s23 H4N2: h85 H6Si2: d791 C1 CBr4: c13 CBrClF2: b301 CBrCl3: b432 CBrF3: b434 CBrN: c325 CBr2F2: d93 CBr4: c13 CClF3: c264 CClNO3S: c249 CCl2F2: d218 CCl3D: c146 CCl3F: t237 CCl4: c14 CCl4S: t240 CD2Cl2: d236 CD4O: m36 CD7O: m40 CFCl3: f30 CF4: c15 CHBrCl2: b316 CHBr2Cl: d88

CHBr2F: d104a CHBr3: t204 CHClF2: c101 CHCl2F: d233 CHCl3: c145 CHF3: t307 CHF3O3S: t308 CHI3: i33 CH2BrCl: b305 CH2Br2: d110 CH2Cl2: d235 CH2F2: d409 CH2I2: d452 CH2N2: c318, d63 CH2N4: t131 CH2O: f32 (CH2O)x: p1 CH2O2: f36 CH2O3: g29 CH2S3: t451 CH3Br: b354 CH3Br3Ge: m260 CH3Cl: c157 CH3ClO2S: m36 CH3Cl3Si: m450, t242 CH3DO: m39 CH3F: f18 CH3I: i37 CH3NO: f33 CH3NO2: m325, n56 CH3NO3: m324 CH3N5: a294 CH4: m33 CH4Cl2Si: d240

CH4N2O: f38, u16 CH4N2S: t161 CH4N4O2: n54 CH4O: m38 13 CH4O: m41 CH4O2: m279 CH4O3S: m34 CH4S: m37 CH5AsO3: m137 CH5N: m127 CH5NO3S: a201 CH5N3: g30 CH5N3S: t160 CH6ClN3O: s3 CH6N2: m274 CH6N4: a180 CH6N4O: c9 CI4: c16 CN4O8: t123 CS2: c10 CO: c11 COS: c12 C2 C2Br2ClF3: d90 C2Br2Cl4: d129 C2Br2F4: d130 C2Br2O2: o54 C2ClF3: c263 C2Cl2F4: d270b, d271 C2Cl2O2: o55 C2Cl3F3: t256, t257 C2Cl3N: t222

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C2Cl4: t38 C2Cl4F2: d411, d412, t36 C2Cl4O: t224 C2Cl6: h27 C2D3N: a30 C2D4O2: a21 C2D6OS: d698 C2F4: t65 C2F6: h42 C2F6O5S2: t309 C2HBrClF3: b308 C2HBr2F3: d133 C2HBr2N: d77 C2HBr3: t203 C2HBr3O: t199 C2HBr3O2: t200 C2HClF2: c100a C2HClF2O2: c98 C2HCl3: t235 C2HCl3O: d186, t218 C2HCl3O2: t219 C2HCl5: p7 C2HF3O2: t300 C2H2: a41 C2H2BrClO: b255 C2H2Br2: d99, d100 C2H2Br2F2: d92 C2H2Br2O: b254 C2H2Br2O2: d76 C2H2Br4: t16 C2H2ClF3: c262 C2H2ClN: c30 C2H2Cl2: d227, d228, d229 C2H2Cl2O: c34 C2H2Cl2O2: d182 C2H2Cl3NO: t217 C2H2Cl4: t36a, t37 C2H2F2: d408 C2H2F3NO: t299 C2H2F4: t64 C2H2N2S3: d488 C2H2O: k1 C2H2O2: g28 C2H2O3: g29 C2H2O4: o52, o53 C2H3Br: b336 C2H3BrO: a35 C2H3BrO2: b249 C2H3Br2Cl3Si: d101 C2H3Br3O: t202 C2H3Cl: c129 C2H3ClF2: c100 C2H3ClO: a37, c23a C2H3ClO2: c27, m194 C2H3Cl3: t231, t232

C2H3Cl3O: t233 C2H3Cl3Si: t258 C2H3DO2: a20 C2H3FO: a43 C2H3FO2: f5 C2H3F3O: t305 C2H3F3O3S: m453 C2H3IO: a48 C2H3IO2: i21 C2H3N: a29 C2H3NO: m288 C2H3NS: m294, m440 C2H3N3: t197 C2H3N3S2: a284 C2H4: e131 C2H4BrCl: b303 C2H4BrNO: b247 C2H4Br2: d96, d97 C2H4ClNO: c24 C2H4ClO: b165a C2H4Cl2: d225, d226 C2H4Cl2O: d237 C2H4Cl6Si2: b227 C2H4F2: d407 C2H4INO: i20 C2H4I2: d451 C2H4N2: a109 C2H4N2O2: o58 C2H4N2S2: d795 C2H4N4: a289, d281 C2H4N4O2: a314 C2H4O: e147 C2H4OS: t147 C2H4O2: a19, h87, m257 C2H4O2S: m16 C2H4O3: h88, p60 C2H4O5S: s26 C2H4S: e148 C2H5AlCl2: e61 C2H5Br: b329 C2H5BrNaO2S: b330 C2H5BrO: b331, b369 C2H5Cl: c121 C2H5ClHg: e198 C2H5ClO: c122, c156, c173 C2H5ClS: c174 C2H5Cl2OPS: e124 C2H5Cl2O2P: e123 C2H5Cl3Si: c171, e269, t236 C2H5DO: e28 C2H5F: f17 C2H5I: i31 C2H5IO: i32 C2H5N: e146 C2H5NO: a5, a6, m255, m291

C2H5NO2: e225, g26, m187, n52 C2H5NO3: e224 C2H5NS: t138 C2H5N3O2: b238, o57 C2H6: e20 C2H6AlCl: d533 C2H6BrN: b333 C2H6Cd: d578 C2H6ClN: c126 C2H6ClNO2S: d692 C2H6ClO2PS: d582 C2H6Cl2Si: d222 C2H6Hg: d631 C2H6N2: a8 C2H6N2O: m460, n78 C2H6N2O2: m275 C2H6N2S: m444 C2H6N4O: o56 C2H6O: d603, e27 C2H6OS: d697, m20 C2H6O2: e21a, e135 C2H6O2S: d696 C2H6O3S: d695, e25, m301 C2H6O4S: d693 C2H6O5S2: m35 C2H6S: d694, e26a C2H6S2: d600, e24 C2H6Te: d700 C2H6Zn: d709 C2H7AsO2: d560 C2H7ClSi: c111 C2H7N: d534, e63 C2H7NO: a162, a163, e29 C2H7NO3S: a160 C2H7NO4S: a169 C2H7NS: a161 C2H7N5: b137 C2H7O3P: d625 C2H8N2: d623, d624, e21, e133 C2H8N2O: h125 C2H9BD: b243 C2H10BN: b242 C3 C3Br2F5: d105 C3Cl3N3: t255 C3Cl3N3O3: t239 C3Cl6: h30 C3Cl6O: a27, h2 C3F6: h44 C3HCl5O: p5 C3H2ClN: c35 C3H2Cl2O2: m6

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C3H2Cl4O: t31 C3H2Cl4O2: t234 C3H2F6O: h43 C3H2N2: m5 C3H2O2: p248 C3H3Br: b415 C3H3Br2N: d126 C3H3Cl: c241 C3H3ClO: a63a C3H3Cl3O: e18, t221 C3H3Cl3O2: m449 C3H3F3O: t302 C3H3F3O2: m452 C3H3N: a63 C3H3NOS2: r7 C3H3NO2: c320 C3H3NS: t136 C3H3N3O2S: a244 C3H3N3O3: a289, c332 C3H4: a72, p246 C3H4BrClO: b410, b411 C3H4BrN: b408 C3H4Br2: d124 C3H4Br2O: b409 C3H4Br2O2: d125 C3H4ClN: c233 C3H4Cl2: d265, d266 C3H4Cl2O: c235, c236, d183, d184 C3H4Cl2O2: m227 C3H4F4O: t66 C3H4N2: i3, m241, p254 C3H4N2O: c287 C3H4N2O2: h84 C3H4N2S: a285 C3H4N3NaS: c326 C3H4O: p203, p249 C3H4O2: a62, o64 C3H4O3: e132, o65, p210 C3H4O4: m3 C3H5Br: b314, b404, b405 C3H5BrO: b328, b403 C3H5BrO2: b406, b407, m143 C3H5Br3: t206 C3H5Cl: c236a C3H5ClO: c120, c232, p216 C3H5ClO2: c228, c229, e109, m188 C3H5Cl3: t247 C3H5Cl3Si: a98 C3H5F3O3S: m453 C3H5I: a87, i50 C3H5N: p215 C3H5NO: c323, h172, h173, v11

C3H5NO2: o59 C3H5NS: e193, m435 C3H5NS2: m26 C3H5N3O: c321 C3H5N3O9: g22 C3H5N3S: c293 C3H6: c406, p204 C3H6BrCl: b307 C3H6BrNO3: b381 C3H6Br2: d120, d121 C3H6Br2O: d122, d123 C3H6ClI: c155 C3H6ClNO: d578 C3H6Cl2: d262, d263 C3H6Cl2N2O2: d173 C3H6Cl2O: d231, d264 C3H6Cl2Si: d241 C3H6Cl4Si: t230 C3H6I2: d454 C3H6NO: a61 C3H6N2: d583 C3H6N2O: i5 C3H6N2O3: m4 C3H6N2OS: a58 C3H6N2O2: m4, m270 C3H6N2S: a286, i4 C3H6O: a26, a78, e15, m462, p211, p232 C3H6OS: t159 C3H6O2: d734, e16, e154, h90, m122, p213 C3H6O2S: m22, m23, m298 C3H6O3: d445, d580, L1, L2, m43, m265, t407 C3H6O3S: p197 C3H6S: p205, p233 C3H6S3: t450 C3H7Br: b400, b401 C3H7BrO: b402 C3H7Cl: c172, c225, c226 C3H7ClO: c132, c153, c230, c231 C3H7ClOS: c156 C3H7ClO2: c227 C3H7ClO2S: p196 C3H7Cl2OP: p241 C3H7Cl3Si: d214, p242 C3H7I: i48, i49 C3H7N: a76, p231 C3H7NO: a28, d606, m120, p212 C3H7NO2: a68, a69, a70, e102, i125, m264, n73, n74 C3H7NO2S: c411 C3H7NO3: i124, n75, p238, s4

C3H7NS: d704 C3H8: p188 C3H8BrClSi: b366 C3H8ClN: c225 C3H8Cl2Si: c88, d232 C3H8N2O: d708, e274 C3H8N2O2: e103 C3H8N2S: d705 C3H8O: e10, e210, p201, p202 C3H8OS2: d485, m315 C3H8O2: d507, m71, p191, p192 C3H8O2S: m21 C3H8O3: g19 C3H8S: e221, p198, p199 C3H8S2: p195 C3H9Al: t352 C3H9BO3: t338 C3H9B3O6: t339 C3H9BrGe: b437 C3H9BrSi: b438 C3H9ClGe: c265 C3H9ClSi: c266 C3H9IOS: t400 C3H9IS: t399 C3H9ISi: i56 C3H9N: i100, p223, t354 C3H9NO: a263, a264, a265, a266, m77, m131 C3H9NO2: a262 C3H9N3Si: a309 C3H9O3P: d635, t390 C3H9O4P: t389 C3H10N2: d54, d55, m254, p189, p190 C3H10N2O: d56 C3H10O3Si: t343 C3H11Br2N3S: a171 C4 C4Cl6: h23 C4Cl6O3: t220 C4D6O3: a23 C4F6O3: t301 C4HBrO3: b352 C4HCl3N2: t248 C4HF7O2: h2 C4H2: b452 C4H2Br2S: d131 C4H2Cl2N2: d267 C4H2Cl2O2: f43 C4H2Cl2S: d272 C4H2F6O2: t306 C4H2O3: m2

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C4H2O4: q42 C4H3IS: i52 C4H3N3O4: n88 C4H4: b489 C4H4BrNO2: b422 C4H4Br2O2: d86 C4H4Br2O4: d128 C4H4ClNO2: c247 C4H4ClO3: c28 C4H4Cl2: d213 C4H4Cl2O2: s19 C4H4Cl2O3: c25 C4H4N2: b456, p251, p256, p277, s18 C4H4N2O2: d448, p278 C4H4N2O2S: d437 C4H4N2O3: b1 C4H4N2O5: a73 C4H4N4: d50 C4H4O: f45 C4H4O2: d483 C4H4O3: s16 C4H4O4: f42, m1 C4H4S: t151 C4H5BrO2: b283 C4H5BrO4: b421 C4H5Cl: c74, c74a, c83 C4H5ClN2O2: c184 C4H5ClO: c310, c408, m31 C4H5ClO2: a82 C4H5ClO3: c194, e232 C4H5Cl3O2: e268 C4H5N: b482, c309, c407, m30a, p279 C4H5NO: m47, m295 C4H5NO2: m201, s17 C4H5NO2S: e39 C4H5NO3: h183 C4H5NS: a88, m432 C4H5N3: a278, i8 C4H5N3O: a194 C4H5N3OS: a187 C4H5N3O2: a152, a153, c322, m338 C4H5N4O: d49 C4H6: b448, b449, b610a, b610b C4H6Br2O: b374 C4H6Br2N2O2: d95 C4H6Br2O2: d87 C4H6ClN: c86 C4H6Cl2: c89, d211, d212 C4H6Cl2O: c87 C4H6Cl2O2: m229 C4H6Cl3NSi: t250

C4H6N2: a149, m284, m285, m286 C4H6N2O2: e121, m273 C4H6N2S: a225 C4H6N2S2: d584 C4H6N4O: d39 C4H6N4O3: a71 C4H6O: b488, c306, d421, m27, m407 C4H6O2: b466, b483, b484, b485, b611, b616, b617, c307, c409, m29, m126, v5 C4H6O2S: b450 C4H6O3: a22, a24, m355, o60, p230 C4H6O4: d652, s15 C4H6O4S: m25, t143 C4H6O5: d690, h186, h187, o67 C4H6O6: t1, t2, t3, t4 C4H7Br: b276, b277, b278 C4H7BrO2: b282, b332, b368, b373, e83, m156 C4H7Cl: c79, c80, c81, c181, c182, c312 C4H7ClO: b620, c78, c136, i85 C4H7ClO2: c84, c85, e105, m196, p228 C4H7Cl3O: t241 C4H7FO2: e153 C4H7N: b618, i83 C4H7NO: h153, i115, m28, m99a, m352, p236, p285 C4H7NO2: b467, h146, m351 C4H7NO3: a46, e233, s13 C4H7NO4: a304, i7 C4H7NS: m434 C4H7N3O: c302 C4H8: b477, b478, b479, c333, m399 C4H8BrCl: b298, b306 C4H8Br2: d81, d82, d83, d84 C4H8Br2O: b148 C4H8Br2O2: d85 C4H8Cl2: d210 C4H8Cl2O: b163, d230 C4H8I2: d450 C4H8N2: d535 C4H8N2O: a102 C4H8N2O2: d610, s14 C4H8N2O3: a313, g27 C4H8N2S: a97, t85 C4H8O: b475, b486, b487, b612, c311, e3, e276, i79, m106, m389, m400, t69

C4H8O2: b480, b481, b614, d732, d733, e57, h107, h108, i81. m64, m401, p234 C4H8O2S: e196, m299, t107 C4H8O3: e24, e153, h120, h138, m70, m296, m302 C4H8S: a90, t87 C4H8S2: d792 C4H9Br: b274, b275, b371, b372 C4H9BrO: b337 C4H9BrO2: b319 C4H9Cl: c75, c76, c179, c180 C4H9ClO: a64, c77, c131, m74 C4H9ClO2: c105, c123, m67 C4H9ClSi: c112 C4H9Cl3Si: b604, b603, d215 C4H9Cl3Sn: b600 C4H9F: f21 C4H9I: i26, i27, i38, i39 C4H9N: e53, p280 C4H9NO: a311, b476, b613, d526, i80, m110, m463 C4H9NO2: a133, a133a, a134, b578, b579, h119, i73, n48 C4H9NO2S: a200 C4H9NO3: a185, a186, i72, m341, n49 C4H9NO5: t442 C4H9NSi: c331 C4H9N3O2: c301 C4H10: b454, m390 C4H10AlCl: d320, e62 C4H10ClO2PS: d351 C4H10ClO3P: d350 C4H10Cl2Si: b165 C4H10Cl4Si2: b174 C4H10N2: p178 C4H10N2O: a227 C4H10N2O4S: a8 C4H10O: b473, b474, d365, m397, m398, m404 C4H10OS: e180 C4H10OS2: b208 C4H10O2: b457, b457a, b457b, b458, b563, d504, d505, e40, e141, m105, m393 C4H10O2S: t144 C4H10O2S2: d484, h123 C4H10O3: b198, b472, d361, o62, t378 C4H10O3S: d399 C4H10O4: e19 C4H10O4S: d397

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C4H10S: b470, b471, d398, i104, m394, m395, m396, m406 C4H10S2: b468, d356 C4H10S3: b209 C4H10Zn: d405 C4H11ClSi: c183 C4H11N: b453, b509, b510, b511, d323, d604, i66, m293 C4H11NO: a135, a164, a203, a216, d376, d539, e44, e67, m112 C4H11NO2: a215, d297, d506 C4H11NO3: t439 C4H11OP: d390 C4H11O2PS2: d358 C4H11O3P: d375 C4H12BrN: t93 C4H12ClN: d324, t94 C4H12Ge: t109 C4H12IN: t95 C4H12N2: b455, b560, b562, d41, d605, m391, m392 C4H12N2O: a165 C4H12N2S4: b183 C4H12OSi: m119 C4H12O2Si: d502 C4H12O3Si: m455 C4H12Pb: t112 C4H12Si: t118 C4H12Sn: t121 C4H13N3: d362 C4H14BN: b239 C4H14OSi2: t106 C4H16O4Si4: t104 C5 C5Cl5N: p10 C5Cl6: h25 C5D5N: p258 C5H3BrS: b426, b427 C5H3Br2N: d127 C5H3ClOS: t153 C5H3ClO2: f55 C5H3ClS: c251 C5H3Cl2N: d268, d269 C5H3N3: p252 C5H4BrN: b416, b417 C5H4ClN: c242 C5H4FN: f26 C5H4F8O: o20 C5H4N2O2: p253 C5H4N2O3: n76 C5H4N4O3: u17 C5H4OS: t154

C5H4O2: f44 C5H4O2S: t155 C5H4O3: c285, f54 C5H5ClN2: a148 C5H5ClN2O2: c168 C5H5N: p257 C5H5NO: h179, h180, h181, p271 C5H5NO2: d448, h183 C5H5N3O2: a243 C5H5N3O4: a158 C5H5N5: a61 C5H6: c395, m174 C5H6BrClN2O2: b302 C5H6Br2N2O2: d76 C5H6Cl2NO2: d220 C5H6Cl2O2: g18 C5H6N2: a275, a276, a277, g17, m408, v12 C5H6N2O: a47, a193 C5H6N2OS: h140, h141 C5H6O: m259 C5H6OS: f48, m443 C5H6O2: f50 C5H6O3: g15, h156 C5H6O4: c284, m253 C5H6O4S3: b156 C5H6S: m441, m442 C5H7BN: b244 C5H7BrO3: e91 C5H7ClO2: c205, d581 C5H7ClO3: m189, m190, m195 C5H7N: m417, p51, p52 C5H7NO: e31, f51 C5H7NO2: c324, e115 C5H7N3: a224, d58 C5H7N3O: a188 C5H8: c401, d424, m157, m178, p15, p16, p17, p18, p58 C5H8Br2O2: e122 C5H8N2: d626, d684, e191, p283 C5H8N2O2: d622 C5H8N4O12: p22 C5H8O: c399, c410, d364, e6, m179 C5H8O2: a74, c334, d532, e60, g16, i95, m65, m168, m169, m170, m200, m225, m300, p33, p34, p207, v2, v3, v10, v14 C5H8O3: e237, h121, m123, o63 C5H8O4: d547, g14, m278

C5H9Br: b313, b365 C5H9BrO2: b364, e93, e94, m155 C5H9Cl: c93 C5H9ClO: c206, d681, m186, p45, t75, t351 C5H9ClOS: c238 C5H9ClO2: b538, c237, e110, e111, i68, i107, m193 C5H9N: d683, m185, p35 C5H9NO: b565, b566, c400, d531, e53, e234, m419, m461 C5H9NO2: d523, f39, m130, p187 C5H9NO4: g12 C5H10: c396, m165a, m166, m167, p48, p49, p50 C5H10Br2: d117, d118 C5H10ClNO: d348 C5H10Cl2: d209 C5H10Cl2: d251 C5H10I2: d453 C5H10NO3P: d293a C5H10N2: d548 C5H10N2O: d627 C5H10N2O3: g13 C5H10N2O4S2: c412 C5H10O: a85, c398, d653, d677, e252, m165, m171, m172, m173, m180, m181, m429, p28, p42, p43, t83 C5H10OS: m439 C5H10O2: b557, c398, d521, d679, e252, h147, h164, i69, i99, m86, m182, m183, m184, m237, m290, m353, p38, p222, t71, t349 C5H10O2S: e197, e222, m316, m431 C5H10O3: d349, d520, e194, m75, m282, m307 C5H10O4: b201, m72 C5H10O5: a300, r9, x8 C5H11Br: b362, b363, b387, b388 C5H11BrO: b322 C5H11BrO2: b320 C5H11Br2O: b148 C5H11Br2O2: b150 C5H11Cl: c109, c150, c169a, c170, c204a C5H11ClO: c110 C5H11Cl2N: b164 C5H11I: i47

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C5H11N: a85, c404, m418, p180 C5H11NO: b558, d369, d678, m317, t72 C5H11NO2: a248, a249, b133, b532, e275, i92, m310a, v4 C5H11NO2S: m42 C5H11NO3: n58 C5H11NS2: d357 C5H11O5P: t391 C5H12: d673, m155, p29 C5H12Cl2O2Si: b162 C5H12N2: a261, m381, m382 C5H12N2O: b608, d702, t122 C5H12N2O2: b533, o46 C5H12N2S: t119 C5H12N2S2: p282 C5H12O: b572, d676, e254, m161, m162, m163, m164, p31, p32, p39, p40, p41 C5H12O2: b504, d307, d518, d519, d675, i97, m64, p218 C5H12O2Si: d509, t395, v18 C5H12O3: m73, t340, t377, t440 C5H12O3S: p36 C5H12O4: p19 C5H12O5: x7 C5H12S: b577, e255, m159, m160, p37 C5H12Si: t401 C5H13ClOSi: c125 C5H13N: a246, a247, d380, d628, d682, m175, m176, p54 C5H13NO: a209, a250, d546, d547, e54, p224 C5H13NOSi: t394 C5H13NO2: a176, d508, d545, d607, m230 C5H13N3: t110 C5H14ClN3O: g5 C5H14N2: d549, d674, p30, t105, t113 C5H14N2O: a150, a166 C5H14O: b560, b561 C5H14OSi: e56 C5H15NSi: d707 C5H15N3: a175 C6 C6BrD5: b263 C6BrF5: b386 C6Cl4O2: t34, t35 C6Cl5NO2: p8

C6Cl6: h22 C6D6: b11 C6D12: c348 C6F6: h41 C6F14: t42 C6HBr5O: p4 C6HCl4NO2: t39 C6HCl5: p6 C6HCl5O: p9 C6H2BrFN2O4: b324 C6H2Br4: t14 C6H2Cl3NO2: t243 C6H2Cl4: t32, t33 C6H3Br2F: d103, d104 C6H3Br2NO2: d115 C6H3Br3O: t211 C6H3ClFNO2: c141 C6H3ClF2: c99 C6H3ClN2O4: c114, c115 C6H3ClN2O4S: d712 C6H3Cl2NO2: d245, d246, d247, d248 C6H3Cl2NO3: d249 C6H3Cl3: t227, t228, t229 C6H3Cl3O: t244, t245 C6H3Cl3O2S: d201 C6H3D3: b9 C6H3FN2O4: d718 C6H3F2NO2: d410 C6H3F3: t303 C6H3N3O6: t403, t404 C6H3N3O7: p174 C6H4BrCl: b287, b288, b296 C6H4BrClO2S: b264 C6H4BrF: b340, b341, b342 C6H4BrNO2: b378 C6H4BrN3O4: b323 C6H4Br2: d79, d112 C6H4Br2N2O2: d114 C6H4Br2O: d119 C6H4Br3N: t201 C6H4ClF: c137, c138 C6H4ClFO: c142 C6H4ClI: c154 C6H4ClNO2: c192, c193, c194 C6H4ClNO3: c201 C6H4ClNO4S: n33 C6H4Cl2: d198, d199, d200 C6H4Cl2N2O2: d244 C6H4Cl2O: d252, d253, d254, d255 C6H4Cl2O2S: c50 C6H4Cl3N: t225, t226 C6H4FNO2: f23 C6H4F2: d406

C6H4INO2: i40, i41 C6H4I2: d449 C6H4N2: a267, c328, c329, c330 C6H4N2O2: b43 C6H4N2O4: d711 C6H4N2O5: d720 C6H4N4O6: t402 C6H4O2: b58 C6H5BO2: c22 C6H5Br: b262 C6H5BrO: b392, b393, b394 C6H5BrS: b428 C6H5Cl: c47 C6H5ClHg: p129 C6H5ClN2O2: c188, c189, c190, c191 C6H5ClN3O4: c113 C6H5ClO: c208, c209, c210 C6H5ClO2: c102, c103, c244 C6H5ClO2S: b24 C6H5ClO3S: c49 C6H5ClS: c252 C6H5Cl2N: d187, d188, d189, d190, d191, d192 C6H5Cl2OP: p140 C6H5Cl2O2P: p100 C6H5Cl2P: d260 C6H5Cl3Si: p159 C6H5F: f11 C6H5FN2O2: f22 C6H5FO: f28 C6H5FO2S: b25 C6H5I: b28, i23 C6H5NO: n77, p261, p262, p263 C6H5NOS: t148 C6H5NO2: n30, n82, p265, p266, p267 C6H5NO3: h182, n59, n60 C6H5NO4: c288 C6H5N3: b61 C6H5N3O: h104 C6H5N3O4: d710 C6H6: b8 13 C6H6: b10 C6H6AsNO6: h162 C6H6BrN: b256, b257, b258 C6H6ClN: c38, c39, c40 C6H6ClNO: a147, c162 C6H6ClNO2S: c48 C6H6Cl6: h24 C6H6FN: f7, f8 C6H6F9O3P: t447 C6H6HgO: p130

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C6H6IN: i22 C6H6NO6: n20 C6H6N2O: e49, p259, p260, p264 C6H6N2O2: n23, n24, n25 C6H6N2O3: a238, a239, a240, m94 C6H6N4O4: d721, n53 C6H6O: p65 C6H6OS: a57, m443 C6H6O2: a44, c21, d428, d429, d430, h86, m258, r2 C6H6O2S: b21, t152 C6H6O3: b34, m259a, t317, t318 C6H6O3S: b23 C6H6O4: d529 C6H6O6: p206 C6H6S: t156 C6H7AsO3: b12 C6H7BO2: b13 C6H7ClN2: c216, c217 C6H7N: a293, a294, m409, m410, m411 C6H7NO: a252, a253, a254, h155, m113, p273, p274 C6H7NO2: m414 C6H7NO2S: b22 C6H7NO3S: a115, a116, a117, s25 C6H7NS: a287 C6H7N3O2: n65, n66, n67 C6H7O2P: p138 C6H7O3P: p139 C6H8AsNO3: a113 C6H8Br2O2: d107 C6H8Br3O: t205 C6H8ClN3O4S2: a137 C6H8Cl2O2: m228 C6H8N2: a218, a219, a220, a221, a222, a223, d284, m263, p104, p105, p106, p117 C6H8N2O: a204, o69 C6H8N2O2S: b26, s24 C6H8N2O3: d561a C6H8O: c371, d609, d620, h38 C6H8O2: b451, c360, h40, m223 C6H8O3: a36, a311, d599, f47 C6H8O4: d598, d608, d629, d630 C6H8O6: a302, g11, i61 C6H8O7: c289 C6H9Br: b312

C6H9BrO3: b285 C6H9ClO3: e106, e107 C6H9F3O2: b605 C6H9NO: o62, v17 C6H9NOS: m433 C6H9NO2: b540 C6H9NO3: m78, n49 C6H9N3: a156 C6H9N3O2: a157, c317, h83 C6H10: c368, d566, h39, h82, m356 C6H10Br2: d89 C6H10N2: e211, i114, p181 C6H10N2O2: c361 C6H10N2O4: d338 C6H10N2O5: a14 C6H10N4: p27 C6H10O: c366, c370, d31, d362, e12, h77, m224, m368, m370, m372 C6H10O2: a91, c397, d422, e114, e119, e142, e199, h60, h69, h74, h75, m369 C6H10O3: d501, e58, e143, h126, h177, m402, p214 C6H10O4: d385, d634, d691, e22, e137, h54, m276, m303 C6H10O4S: t146 C6H10O4S2: d794, e136 C6H10O5: d386 C6H10O6: d699, g7 C6H10S: d34 C6H11Br: b311 C6H11BrO: b424 C6H11BrO2: b279, b347, b529, e85, e86, e89 C6H11BrO4: d346 C6H11Cl: c91 C6H11ClO: h72 C6H11ClO2: b535, c82, e98 C6H11I: i28 C6H11N: d30, h61, m361 C6H11NO: c367, e260, f40, m388, o61, t379 C6H11NO2: e66 C6H12: c347, d572a, d573, d574, e95a, h73, m222 C6H12Br2: d94, d106 C6H12ClNO: c133 C6H12Cl2: d217, d219, d234 C6H12Cl2O: b166 C6H12Cl2O2: b161, d169 C6H12Cl3O3P: t437 C6H12Cl3O4P: t436

C6H12F3NOSi: m457 C6H12NO3P: d294 C6H12N2: d61, d325, t279 C6H12N2S: b183, t119 C6H12N2S4: t120 C6H12N2Si: t396 C6H12N2Zn: d601 C6H12N4: h49 C6H12O: a96, b609, c365, d572, e11, e98, h51, h70, h71, h76, i78, m367, m430 C6H12O2: b465, b501, b502, b503, c359, d576, d577, e99, e100, e192, e209, e213, h64, h150, i63, m235, m312, m362, m363, m456, p244, t84 C6H12O3: d525, e42, e179, e182, i116, p2, p237, t70 C6H12O4: e149 C6H12O4Si: d27 C6H12O6: f41, g1, g8, i19, m11, s6 C6H12O7: g6 C6H12S: c364 C6H13Br: b346 C6H13BrO2: b317 C6H13Cl: c149 C6H13ClO: c150 C6H13ClO2: c96 C6H13ClO3: c124 C6H13I: i36 C6H13N: c375, e202, h48, m383, m384, m385, m386 C6H13NO: d314, d637, e223, h133, h152 C6H13NO2: a182, a183, h127, i88, L5, L6, m233 C6H13NO4: b199 C6H13NO5: t441 C6H14: d567, d568, h52, m357, m358 C6H14ClN: d328 C6H14Cl4OSi2: b175 C6H14NO2: b213 C6H14N2: a214, c354, d43, d44, d671, e245 C6H14N2O: a172, h129 C6H14N2O2: L13 C6H14N4O2: a301 C6H14O: b554, d476, d570, d570a, d571, d786, e95, h66, h67, h68, m364, m365, m366 C6H14OSi: a93

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C6H14O2: b493, d303, d304, d569, e138, e219, h55, h56, h57, m82, m360, p220 C6H14O2S: d789 C6H14O3: b204, b214, d305, d779, e41, e183, h63, h176, t321, t341 C6H14O4: t280 C6H14O4S: d788 C6H14O4S2: b459 C6H14O6: d824, m10, s5 C6H14O6S2: b210 C6H14S: b557, h62 C6H14Si: a101 C6H15Al: t273 C6H15AlI: d322 C6H15AlO: d321 C6H15As: t276 C6H15B: t277 C6H15ClGe: c260 C6H15ClO3Si: c240 C6H15ClSi: b551, c261 C6H15Ga: t286 C6H15In: t288 C6H15N: d468, d575, d777, e97, h81, m371, t274 C6H15NO: a184, a211, a212, b513, b553, d327, d364, i98 C6H15NO2: d306, d540, e125 C6H15NO3: t266 C6H15N3: a174 C6H15O3B: t268 C6H15O3P: d480, t294 C6H15O3PS: t298 C6H15O4P: t292 C6H15P: t293 C6H15Sb: t275 C6H16Br2OSi2: b149 C6H16Cl2OSi2: b167 C6H16N2: d367, h53, m359, t108 C6H16OSi: p221 C6H16O2Si: d301 C6H16O3SSi: m24 C6H16O3Si: t269, t342 C6H16Si: t297 C6H17NO3Si: a274, t344 C6H17N3: i9 C6H18ClN3Si: c268a C6H18N2Si: b179 C6H18N3OP: h50 C6H18N4: t285, t434 C6H18OSi2: h47

C6H18O3Si3: h45 C6H19NOSi2: b233 C6H19NSi2: h46 C7 C7H3BrClF3: b297 C7H3BrF3NO: b380 C7H3ClF3NO2: c199, c200 C7H3ClN2O5: d714 C7H3Cl2F3: d206, d207 C7H3Cl2NO: d259 C7H3Cl3O: d208, d209 C7H4BrF3: b268, b269 C7H4Br4O: t15 C7H4ClFO: f14, f15 C7H4ClF3: c60, c61, c62 C7H4ClN: c54, c55 C7H4ClNO: c219, c220 C7H4ClNO3: n39, n40 C7H4ClNO4: c195, c196, c197 C7H4Cl2O: c64, c65, d194, d195 C7H4Cl2O2: d202, d203, d204 C7H4Cl3F: t238 C7H4Cl4: c58, c59 C7H4F3NO2: n86, n87 C7H4I2O3: h113 C7H4N2O2: n38 C7H4N2O6: d713 C7H4N2O7: d722, h114 C7H4O3S: h105 C7H4O4S: s27 C7H5BrO: b65 C7H5BrO2: b266, b265 C7H5BrO3: b419 C7H5ClF3N: a142, a143 C7H5ClO: b66, c43, c44, c45 C7H5ClO2: c51, c52, c53, p99 C7H5ClO3: c207, c245, c246 C7H5Cl2F: c139 C7H5Cl2NO: d196, d197 C7H5Cl3: t251, t252, t253, t254 C7H5FO: b68, f9, f10 C7H5FO2: f12, f13 C7H5F3: t311 C7H5F3N2O2: a237 C7H5F3O: t304 C7H5F4N: a179 C7H5IO2: i25 C7H5IO3: i51 C7H5I2NO2: a154 C7H5N: b51 C7H5NO: b62, p124

C7H5NO3: n26, n27 C7H5NO3S: s1 C7H5NO4: n35, n36, n37, p268, p269, p270 C7H5NO5: h163 C7H5NS: b59, p125 C7H5NS2: m17, m19 C7H5N3O2: a234, n34, n55 C7H5N3O2S: a236 C7H5N3O6: t405 C7H6BrClO: b300 C7H6BrNO2: n44 C7H6BrNO3: h156 C7H6Br2: b271, d132 C7H6Br2O: d111 C7H6ClF: c143, c144, f16 C7H6ClNO: c46 C7H6ClNO2: a138, a139, c202, c203, n45 C7H6Cl2: c69, c70, d273, d274, d275, d276 C7H6F3N: a126, a127, a128, t310 C7H6FNO2: f24 C7H6INO2: a199 C7H6N2: a121, a122, a123, b39 C7H6N2O3: n28, n29 C7H6N2O4: a233, d723, d724 C7H6N2O5: d715, d716 C7H6N2S: a125 C7H6N4O2: t134 C7H6O: b3 C7H6OS: t139 C7H6O2: b44, h94, h95, h96, m251 C7H6O2S: m18 C7H6O3: d427, f46, h99, h100, h101 C7H6O4: d431, d432, d433, d434 C7H6O5: t319 C7H6O6S: s31 C7H7Br: b85, b429, b430, b431 C7H7BrO: b259, b260, b270, b357, b358, b359 C7H7BrS: b425 C7H7Cl: b90, c255, c256, c257 C7H7ClNNaO2S: c258 C7H7ClN4O2: c253 C7H7ClO: c66, c160, c176, c177 C7H7ClO2S: t177 C7H7ClO3S: m56

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C7H7ClS: c73 C7H7Cl3Si: b128 C7H7F: f27, f28, f29 C7H7FO: f19, f20 C7H7FO2S: t178 C7H7I: i53, i54, i55 C7H7N: v15, v16 C7H7NO: a53, a54, a55, b4, f35 C7H7NO2: a118, a119, a120, h97, h98, m412, m413, n83, n84, n85 C7H7NO3: a280, a281, m92, m339, m340, n41, n42, n43 C7H7NO4S: c17 C7H7N3: a197, a198 C7H8: b134, c344, t166 C7H8BrN: b360 C7H8ClN: c37, c67, c68, c163, c164, c165, c166, c167 C7H8ClNO: c158, c159 C7H8ClNO2: c19 C7H8ClNO2S: c248 C7H8Cl2Si: d239 C7H8N2: h102 C7H8N2O: a112, b71, p167 C7H8N2O2: d40, h149, h170, m326, m327, m328, m329, m330, m415 C8H8N2O3: m89, m90, m91 C7H8N2S: p158 C7H8N4O2: t133 C7H8O: b78, c303, c304, c305, m55 C7H8O2: d438, h106, m97, m98, m99, m280 C7H8O2S: t172 C7H8O3: e155, f49, m314 C7H8O3S: m139, t176 C7H8S: b106, m379, t142 C7H9BrO2: e84 C7H9N: b79, d685, d686, d687, d688, d689, e256, e257, e258, m134, t180, t181, t182 C7H9NO: a213, b101, h132, m48, m49, m50 C7H9NO2: d524 C7H9NO2S: t173, t174 C7H9NO3S: a205, a206, a288 C7H9NS: m436 C7H10: b135 C7H10ClN3O: g4 C7H10N2: a177, a178, d59, d60, d287, d551, t167, t168, t169, t170

C7H10N2O: o66 C7H10N2O2: e212, m242 C7H10N2O2S: t175 C7H10O: d294, m67, n108, t67 C7H10O2: a40, c402 C7H10O3: e17, e144, m354, t367 C7H10O4: d29, d596, p208 C7H10O5: d528 C7H11Br: b383 C7H11BrO4: d346 C7H11ClO: c351 C7H11N: c350 C7H11NO: c381, h112 C7H11NO2: a52, b539 C7H11NO3: m83 C7H11NO5: a45 C7H11NS: c382 C7H12: c345, h20, m215, m216, n107 C7H12N2O: m464 C7H12O: b506, c348, c352, c369, m212, m213, m214 C7H12O2: a80, b507a, b508, c353, d420, e126, i65 C7H12O3: e43, e201, e226, h178, t73 C7H12O4: d378, d379, d636, d656, h7, m76, m277, t125 C7H12O6Si: m448 C7H13Br: b310, b367 C7H13BrO2: b390, e92 C7H13ClO: h17 C7H13N: a245 C7H13NO: a307, b507, c380 C7H13NO2: d541 C7H13NO3: d418 C7H14: c341, e118a, h18, h18a, h18b, m202 C7H14ClN: c134 C7H14N2: d475 C7H14N2O: a272 C7H14N2O2: e246 C7H14O: c342, c384, d655, d658, h3, h14, h15, h16, m205, m206, m207, m208, m209, m210, m211, m271 C7H14O2: b559, b593, b594, d312, e128, e207, e208, e239, h9, i74, i91, i106, m270, p53, p228 C7H14O2S: b569 C7H14O3: b567, e130, e151 C7H14O6: m262

C7H15Br: b343, b344 C7H15Cl: c147 C7H15ClO2: c97 C7H15I: i34 C7H15N: c362, d672, e247, e248, m218, m219, m220 C7H15NO: e186, h131, h134, m387, p182, p183 C7H15NO2: p286 C7H15NO3: m467 C7H15O5P: t296 C7H16: d654, e238, h6, t361 C7H16BrNO2: a38 C7H16ClNO2: a39 C7H16N2: a210, a271, m308, t392 C7H16N2S: d482 C7H16O: d657, h10, h11, h12, t362 C7H16O2: b498, b499, d311, d393, m405 C7H16O2Si: d310 C7H16O3: d784, t290 C7H16O4: t92, t284 C7H16S: h8 C7H17N: h19, m272 C7H17NO: b500, d332, d333 C7H17NO2: b515, d331 C7H17NO5: m261 C7H18N2: d334, d392, t116 C7H18N2O: b180 C7H18N2O2: a270 C7H18N2O4Si: t348 C7H18O2Si: b607 C7H18O3Si: b606, i77, m451 C7H19NOSi2: b232 C7H19NSi: d404 C7H19N3: d52 C7H20N2OSi2: b236 C7H22O4Si3: h5 C8 C8Br4O3: t17 C8Cl4O3: t40 C8D10: e73 C8F18O2S: p59 C8HCl4NO2: t39 C8H3NO5: n72 C8H4BrNO2: b348 C8H4Cl2O2: b15, b16, p172 C8H4Cl2O4: d261 C8H4Cl6: b225 C8H4F6: b229 C8H4N2: d282, d283

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C8H4N2O2: p107 C8H4O3: p169 C8H5BrN: b272 C8H5ClO2: c224 C8H5Cl3O: t223 C8H5Cl3O3: t246 C8H5D3O: a32 C8H5F3O2S: t132 C8H5F6N: b228 C8H5NO: b67 C8H5NO2: i17, p171 C8H5NO3: h171, i60 C8H5NO6: n31, n32, n70, n71 C8H6: p84 C8H6BrClO: b286 C8H6BrN: b397 C8H6Br2O: d78 C8H6Br4: t18, t19, t20 C8H6ClN: c71, c72, c215 C8H6ClNO3: c187 C8H6Cl2O: c168, d185 C8H6Cl2O3: d256 C8H6N2: q4 C8H6N2O: q5 C8H6N2O2: n64 C8H6O: b42 C8H6O2: b14, p170, t6 C8H6O3: b69, f37, m250 C8H6O4: b17, b18, p168 C8H6S: b60 C8H7Br: b420 C8H7BrO: b251, b253 C8H7BrO2: b356, b396 C8H7BrO3: b355 C8H7ClO: c31, c32, c33, p83, t187, t188, t189 C8H7ClOS: b92 C8H7ClO2: b91, c214, m60, m191, m192, p69 C8H7ClO3: c161, c211 C8H7FO: f6 C8H7N: i15, p82, t183, t184, t185 C8H7NO: m9, m147, t192 C8H7NS2: m438 C8H7NO3: n21, n22 C8H7NO3S: t179 C8H7NO4: a114, m331, m332, m333, m334, m335, m336, m337, n61, n62, n63 C8H7NO5: m93 C8H7NS: b126, m146 C8H7N3O2: a151 C8H8: s11 C8H8BrNO: b248

C8H8Br2: d98, d134, d135 C8H8ClNO: c25, c26, c26a C8H8ClNO3: a146 C8H8ClNO3S: a10 C8H8Cl2: d277, d278, d279 C8H8HgO: p128 C8H8N2: a255, m140 C8H8O: a31, e9, m138, p77, s12 C8H8OS: m437 C8H8O2: b41, b99, h91, h92, h93, m51, m52, m53, m141, m142, m143, m144, p80, p81 C8H8O2S: p156, t157 C8H8O3: d425, h142, h165, m8, m57, m58, m59, m281, m424, p68, r4, t81 C8H8O4: d25, h143 C8H8O4S: a33 C8H8O5: m454 C8H9Br: b334a, b335, b443, b444, b445, b446 C8H9BrO: b321, b338, b361 C8H9BrO2: b318 C8H9Cl: c127, c128, c269, c270, c271, c272, c273 C8H9ClO: c108, c218 C8H9ClO2: c104 C8H9N: b104, i18 C8H9NO: a18, a105, a106, a107, b98, m256 C8H9NO2: a15, a16, a17, a207, a208, b89, d638, d639, d640, d641, e226, e259, m54, m129, p114, t77 C8H9NO3: a202, h167, h168, m95 C8H9NO4: d511 C8H9NO4S: m133 C8H10: e74, x4, x5, x6 C8H10ClN: c107 C8H10N2O: d642 C8H10N2O3: m85 C8H10N2O3S: m343 C8H10N4O2: c1, d286 C8H10O: b136, d659, d660, d661, d662, d663, d664, e36, e240, e241, e242, m116, m117, m118, m149, m150, p109, p110 C8H10O2: b19, d493, d494, d495, e51, m61, m84, p72, p108 C8H10O3: c308, c356, d512, h118, h145, m30, m234

C8H10O3S: e75, m447 C8H10O4: d668, d669, d670 C8H10O8: b469 C8H10S: b110 C8H11N: b108, d553, d554, d555, d556, d557, d558, d559, e68, e69, e70, e220, i130, m151, m152, p112, t393 C8H11NO: a173, a251, a256, a257, a295, d544, e32, h122, m62, m80, m81, p101, p275, p276 C8H11NO2: d488, d489, d490 C8H11NO2S: m446 C8H11NO3: e150 C8H12: c387, c388, v9 C8H12N2: d288, d665, t117, x9 C8H12N2O2: d461 C8H12N2O3: d339 C8H12N4: a313 C8H12O: e278 C8H12O2: d589, e262, n109 C8H12O3: e135, t74 C8H12O4: c355, d28, d370, d377, m36 C8H12O5: d530 C8H12O6Si: t194 C8H13N: e238 C8H13NO4: m342 C8H14: c393, o19, o49, v8 C8H14N2: p185, p281 C8H14NO4: d472 C8H14O: b576, c392, d592, d621, m217, m269, o50 C8H14O2: b464, b570, c373, c374, c405, d620, h78, i71, m203, n31 C8H14O3: b505, b615, e45, e101, i64, i82 C8H14O4: b197, b460, d381, d396, d617, e139, e177, o25 C8H14O4S: d703 C8H14O4S2: d793 C8H14O6: d400, d401 C8H15BrO2: e88 C8H15ClO: e163, o39 C8H15N: o28 C8H15NO: p243 C8H15NO2: d543, e249, e250, p184 C8H16: c389, d585, d586, d587, d587a, d588, e117, o40, t384 C8H16Br2: d116 C8H16N2O4S: h130

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DEAN #37261

LEFT

(McGHP)

1.68

INTERACTIVE

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C8H16O: c378, c391, d500, d590, d591, e118, e158, m268, o36, o37, o38, o43 C8H16O2: b531, c357, c390, e160, e161, h79, i70, m266, o30, p239 C8H16O3: b497, e181 C8H16O4: c313, e37, t124 C8H17Br: b385 C8H17Cl: c204 C8H17Cl3Si: o48 C8H17I: i44 C8H17N: b597, c394, d593, d594 C8H17NO3: e173 C8H17O5P: t295 C8H18: d616a, e158a e214, e215, o23, t100, t380, t381, t382 C8H18AlCl: d455 C8H18ClNO2: a49 C8H18Cl2Sn: d177 C8H18F3NOSi2: b235 C8H18N2: c349 C8H18N2O4S: h130 C8H18N2O6S2: p179 C8H18O: d148, d458, e162, m267, o32, o33, o34, o35, o66a C8H18OSi2: d799 C8H18OSn: d180 C8H18O2: b494, d159, d618, e159, o26, o27, t383 C8H18O2S: d173 C8H18O3: b186, b495, t289 C8H18O3S: d172 C8H18O3Si: t272 C8H18O4: b211, t282 C8H18O4S: d169 C8H18O5: t51 C8H18S: d170, d171, o29 C8H18S2: b154, b155, d146, d147 C8H18Si2: b231 C8H19Al: d456 C8H19N: d139, d140, d457, d477, d619, e166, o44, t103 C8H19NO: d413 C8H19NO2: b549, d299, d300 C8H19O3P: d164 C8H20BrN: t49 C8H20ClN: t50 C8H20Ge: t58 C8H20N2: o24, t101, t102 C8H20N2O2S: t61

C8H20O3Si: e270 C8H20O4Si: t48 C8H20O4Ti: t163 C8H20Pb: t59 C8H20Si: t60 C8H20Sn: t63 C8H21NOSi2: b230 C8H21NO2Si: a269, d308 C8H22B: b241 C8H22N2O3Si: a166, t346 C8H22N4: b145 C8H22O2Si2: b234 C8H23N5: t56 C8H24Cl2O3Si4: d250 C8H24O2Si3: o22 C8H24O4Si4: o21 C8H35N: d728 C9 C9H2Cl6O3: h28 C9H3Cl3O3: b33 C9H4O5: b32 C9H5BrClNO: b304 C9H5Br2NO: d108 C9H5ClINO: c152 C9H5Cl2N: d270 C9H6BrN: b418 C9H6ClNO: c153 C9H6INO4S: h137 C9H6N2O2: t171 C9H6O2: b55, c292 C9H6O3: h111 C9H6O4: i13 C9H6O6: b29, b30, b31 C9H7BrO: b309 C9H7ClO: c280 C9H7ClO2: c90 C9H7N: i133, q3 C9H7NO: h184 C9H7NO3: h151, m289 C9H7NO4: n50 C9H7NO4S: h185 C9H7N3O4S2: a242 C9H8: i14 C9H8Cl2O3: d258 C9H8N2: m423, p120 C9H8N2O6: e129 C9H8O: c278, i12 C9H8O2: c279, d417, v6 C9H8O3: h109 C9H8O3S: p247 C9H8O4: p127 C9H9BrO: b412 C9H9BrO2: b86

C9H9Cl: v7 C9H9ClO: c234 C9H9ClO3: c213, d498 C9H9N: d564, m287 C9H9NO: m103, m104, p134 C9H9NO2: a9 C9H9NO3: a11, a12, b70 C9H9NO4: e227 C9H9N3O: a260 C9H9N3O2S2: t137 C9H9N5: d53 C9H10: a78, i10, m425, m426 C9H10Br2: d109 C9H10F3NO2: m135 C9H10N: a196, a197 C9H10N2: a296, p121 C9H10N2O: p151 C9H10N2O2: p85 C9H10N2O3: a129 C9H10O: a94, a95, c282, e14, e72, i11, m124, p147, p148, p149, p209, p217 C9H10O2: b63, b76, d563, e33, e34, e76, h174, h175, m44, m45, m46, m309, m310, m311, m375, p103, p150, t190 C9H10O3: d491, d492, e37, e38, e46, e55, e178, e261, f52, m101, m283, m297, m304, m305, p74 C9H10O4: d496, d492, h135, m292 C9H11Br: b350, b353, b399, b435, b436 C9H11BrO: b413, p75 C9H11Cl: c222 C9H11ClO3S: c135 C9H11N: a77, c333, m288, t78, t86 C9H11NO: d536, d562, m121, m374, m445 C9H11NO2: d537, d538, e35, e64, e65, i126, p86 C9H11NO3: t455 C9H12: e190, i103, p225, t357, t358, t359, v13 C9H12N2O4: a241 C9H12N2O6: u18 C9H12N2S: b111 C9H12O: b98, d632, d633, i127, i128, i129, m373, p145, p146, p240, t385, t386, t387 C9H12O2: b115, c316, c358, e48, p73, p148, t365, t374

short standard long

DEAN #37261

(McGHP)

RIGHT

ORGANIC COMPOUNDS

INTERACTIVE

1.69

top of rh base of rh cap height base of text

TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C9H12O3: d499, m204, t332, t333, t334 C9H12O3S: e263 C9H12S: p144 C9H13N: b595, d565, d706, e80, e203, e264 e265, e266, i101, t355 C9H13NO: b80, m96, n110 C9H13NO2: a258, b596 C9H13N5: t191 C9H14BrN: p162 C9H14Br3N: p165 C9H14ClN: p163 C9H14IN: p164 C9H14N2: n92, t388 C9H14O: d611, d613, i93, t364 C9H14O2: m350 C9H14O2Si: d510 C9H14O3: b215, t76 C9H14O3Si: p161 C9H14O5: d315, d382 C9H14O6: p200 C9H14Si: p166 C9H15N: t195 C9H15NO: c362 C9H15N3: t439 C9H16: m348 C9H16N2: d62 C9H16O: d612, n103 C9H16O2: b571, c363, h80, n97 C9H16O3: b568, b582 C9H16O4: d368, d371, d478, d614, n93 C9H16O6: d345 C9H17BrO2: e87 C9H17Cl: c92 C9H17ClO: n102, t372 C9H17ClO2: e167 C9H17N: a83, n95 C9H17NO2: e216, e217 C9H18: i108, p229, t363 C9H18NO: t115 C9H18N2O: d550 C9H18O: c385, d616, n99, n100, n101, n104, t370 C9H18O2: e156, m349, n96 C9H18O3: d144 C9H18O4: d785 C9H19Br: b382 C9H19BrO2: e90 C9H19I: i42 C9H19NO: d151 C9H19NO3Si: t270 C9H19N2S: d175

C9H20: d386a, d613a, e210a, n90, t370a C9H20Cl2Si: d238 C9H20N2: a136, a290 C9H20N2S: d136 C9H20O: d615, n98, t371 C9H20O2: b556, n94 C9H20O2Si: c377 C9H20O3: d783, t291 C9H20O3Si: a99 C9H20O4: t430 C9H21Al: t428 C9H21BO3: t427, t326 C9H21BO6: t445 C9H21ClO3Si: c239 C9H21N: n105, t429 C9H21NO2: d470, d778 C9H21NO3: t325 C9H21N3: t287 C9H21O3P: t329 C9H22N2: d387, n91 C9H22O3: d780, d781 C9H22Si: t330 C9H23N3: p26 C9H24N4: b147 C9H24O2Si3: m153 C9H27BO3Si3: t449 C9H31ClO3Ti: c254 C10 C10H2O6: b28 C10H4Cl2O2: d243 C10H6Br2O: d113 C10H6Cl2O: d242 C10H6N2: b103 C10H6N2O4: d719 C10H6N2O4S: d64 C10H6O2: n11 C10H6O3: h161 C10H6O8: b27 C10H7Br: b376 C10H7BrO: b377, b378 C10H7Br2NO: d112 C10H7Cl: c185, c186 C10H7NO2: n57, n80, p126 C10H7NO8S2: n81 C10H8: a316, d1, n2 C10H8BrNO2: b339 C10H8N2: d790 C10H8N2O4: b205, f53 C10H8O: n9, n10 C10H8O2: d439, d440, d441, d442, m199 C10H8O3: h148

C10H8O3S: n6, n7 C10H8O4: d443, d444 C10H9N: a228, a229, m420, m421, m422, n17 C10H9NO: a51, a232 C10H9NO2: i16 C10H9NO3: h128 C10H9NO3S: a230 C10H9NO4S: a189, a190, a191, a192 C10H9NO6: d643 C10H10: d423 C10H10BrClO: b299 C10H10ClFO: c121 C10H10ClNO2: c29 C10H10Cl2O3: d257 C10H10N2: a279, n4, n5 C10H10N2O: m378 C10H10N4O2S: s21 C10H10O: d363, m197, p94, p95 C10H10O2: b63, m66, m198, s2 C10H10O3: b72, m345 C10H10O4: d590, d591, d592, m125, p155, r3 C10H11BrO: b375 C10H11ClO3: c212 C10H11ClO4: t336 C10H11IO4: i24 C10H11N: p98 C10H11NO2: a24, d514 C10H11NO4: c8, d552a C10H11O2S: b94 C10H12: d292, t80 C10H12N2: a170, b81 C10H12O: a89, b77a, b619, e59, e279, i84, i102, m107, m403, p96 C10H12O2: d419, e204, e205, e206, e243, h154, h166, m79, m102, m108, m109, m111, m148, p79, p97, p111, p226 C10H12O3: d487, e47, e195, m306, p71, p102, p235 C10H12O4: d26a, d513, m231, m232, t331 C10H12O5: p245, t335 C10H13Br: b280, b351 C10H13BrO: b281 C10H13BrO2: b395 C10H13Cl: b536, c178 C10H13NO: d527, p131 C10H13NO2: m380 C10H13NS2: b95

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DEAN #37261

LEFT

(McGHP)

1.70

INTERACTIVE

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C10H13N5O4: a67 C10H13O2S: b94 C10H14: b521, b522, b523, d340a, d341, d342, i67, i118, i119, i120, t97, t98, t99 C10H14ClN: c130 C10H14NO5PS: p3 C10H14N2: n19, p141 C10H14N2O: d383 C10H14N2O4: b206 C10H14N4O4: d446 C10H14O: c20, i104 C10H14O: b585, b586, b587, b588, b591, c20, i104, i121, i122, i123, k2, m376, t162a, t260 C10H14O2: b534, d516, p78 C10H14O3: c7 C10H14O4: b461, e23, e140, m100, t337 C10H14O5PS: p3 C10H15BrO: b284 C10H15N: b516, b517, b518, b519, d336, d278, e2, e277, i105, i117, m377, p96 C10H15NO: b490, c403, d330, e2, p219 C10H15NO2: d517 C10H15NO4: d309 C10H16: a65, c2, d595, d648, d736, L7, L8, m467, p25, p175, p176, t10, t11, t259, t400a C10H16ClN: b131 C10H16Cl2O2: d13 C10H16N2: d388 C10H16N2O4: d35 C10H16N2O8: e134 C10H16O: c3, c4, c286, d416, d614, d645, L9, L10, p177, p250, t376 C10H16O2: c383, m344 C10H16O4: c4, d319 C10H16O4S: c5 C10H16O5: d317, d366 C10H16Si: b132 C10H17N: a64, p284 C10H17NO: c386, m465 C10H18: d2, d3 C10H18NO2: b514 C10H18N2O7: h124 C10H18O: b245, b545, b546, c277, d4, g2, i62, i132, L11, m13, t12, t13, t375

C10H18O2: c379, d17, d650 C10H18O3: d680, t77, t350, v1 C10H18O4: b185, d10, d158, d318, d394, d651, t283 C10H18O6: d481 C10H18S2: b154 C10H19ClO: d21 C10H19N: d13, d13a, t356 C10H19NO2: d329, e251 C10H20: b541, b542, c335, d22 C10H20Br2: d91 C10H20Cl2: d216 C10H20N2S4: t62 C10H20O: b543, b544, c290, d7, d18, d19, d20, e7, e175, m12, m313 C10H20O2: d15, e164, e231, m177, o42 C10H20O4: b496, b530 C10H20O5: p46 C10H20O5Si: t347 C10H21Br: b315 C10H21Cl: c94 C10H21I: i29 C10H21N: d353 C10H21NO: a226 C10H21NO2: e218 C10H21NO4Si: t271 C10H22: d8 C10H22N2: d51 C10H22O: d16, d646, d647, d738, t79 C10H22O2: d11, d12, d137 C10H22O3: d699, t433 C10H22O4: t432 C10H22O5: b212, p47, t55 C10H22O7: d735 C10H23N: d23, d649, d737 C10H23NO: d141 C10H23NO2: d313 C10H24N2: d9, t57, t111 C10H24N2O2: d731 C10H24N4: b146, t89 C10H24O3Si: i76 C10H28N6: p23 C10H30O3Si4: d6 C10H30O5Si5: d5 C11 C11H7N: c327 C11H7NO: n18 C11H8O: n1 C11H8O2: h157, m321, n3 C11H8O3: h158, h159, h160

C11H9Br: b370 C11H9Cl: c175 C11H9N: p152 C11H10: m318, m319 C11H10O: m87, m88 C11H12ClF: c140 C11H12N2O: a299 C11H12N2O2: t454 C11H12O2: b107, c281, e112, m115 C11H12O3: b77, b200, e77, e145, e244 C11H13ClO: b527 C11H13ClO3: c259 C11H13NO: b124, d666 C11H13NO4: b580 C11H13N3O: a110 C11H14O: p44, m114 C11H14O2: a84, b524, b526, d522, e52, e176, p113 C11H14O3: b491, b584, b590, e200 C11H14O4: e158 C11H15N: p142 C11H15NO: b121, d326 C11H15NO2: b512, d542, e127 C11H16: b602, p24, p55 C11H16N2: b119 C11H16O: b87, b573, b574, b575, d667, p57 C11H16O4: d800 C11H17N: b538, d403 C11H17NO: e267 C11H17NO2: b109, m416 C11H17O3P: d344 C11H18N2O2: t366 C11H18O: d372, n106 C11H18O5: d316 C11H19ClO: u15 C11H19NO2: e168, o45 C11H20O: u12 C11H20O2: e165, i89, u13 C11H20O4: d155, d347, d354, d373 C11H21BrO2: b442 C11H21N: u3 C11H21O2: c287 C11H22: u12a C11H22N2: d776 C11H22O: u1, u9, u10, u11, u14 C11H22O2: e171, e228, m69, m226, u4, u5, u6 C11H23Br: b441 C11H23I: i57 C11H24: u2

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

1.71

ORGANIC COMPOUNDS

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C11H24O: u7, u8 C11H24O6Si: t444 C11H25NO2: a292 C11H26N2: b555, d166 C11H26N2O6: b237 C12 C12H4Cl6S2: b226 C12H6Br4O4S: s28 C12H6O3: n8 C12H6O12: b20 C12H7Cl6O: d296 C12H8: a3 C12H8Br2: d80 C12H8Cl2OS: b172 C12H8Cl2O2S: b171, c223 C12H8N2: p63 C12H8N2O4S: b216 C12H8O: d66 C12H8S: d67 C12H9Br: b273 C12H9BrO: b325, b398 C12H9ClO2S: c221 C12H9N: c6, d751, n16 C12H9NO: b73, b74, b75 C12H9NO2: n46, n47 C12H9NO3: n68, n69 C12H9NS: p67 C12H9N3O4: d717 C12H10: a2, b138 C12H10ClN: a145 C12H10ClO3P: c748 C12H10ClP: c118 C12H10Cl2Si: d223 C12H10Hg: d758 C12H10N2: a312 C12H10N2O: n79, p90 C12H10N2O2: n51 C12H10N3O3P: d764 C12H10O: d753, m322, m323, p135, p136 C12H10OS: d772 C12H10O2: d436, h89, n14, n15 C12H10O2S: d771, t145 C12H10O3: n12 C12H10O3S: b142 C12H10O4: q1 C12H10O4S: s30 C12H10S: d770 C12H10S2: d750 C12H10Se2: d749 C12H11N: a130, a131, b122, b123, d743 C12H11NO: h115, n13, p70

C12H11N3: p88 C12H11O3P: d763 C12H12N2: b140, d757, p137 C12H12N2O: o68 C12H12N2O2: b40 C12H12N2O2S: d47, d48 C12H12O: e50 C12H12O2Si: d769 C12H12O3: e78 C12H12O6: t193, t360 C12H13N: t68 C12H13N3: d34 C12H13NO3S: p272 C12H14: d467 C12H14N2: d46 C12H14N4O2S: s22 C12H14O: b525 C12H14O3: e179 C12H14O4: d391 C12H15NO: b121 C12H15N3O3: t196 C12H15N3O4S: d42 C12H16: b598, c376, m221 C12H16O2: p64 C12H16O3: d298 C12H17N: b120 C12H17NO: d402 C12H18: c338, d473, d474, p116, t453 C12H18Cl2N4OS: t135 C12H18N2: p186 C12H18N2O2: i94 C12H18O: b552, d479, e4 C12H18O2: b550 C12H18O3: o41 C12H18O4: b463, h58 C12H19N: d471 C12H20O2: b202, b296, e112, g3, L12 C12H20O3Si: p160 C12H20O4: d154 C12H20O4Sn: d179 C12H20O7: t278 C12H21N: t446 C12H21NO3Si: t345 C12H21N3: t429 C12H22: c339, d288 C12H22BCl: c95 C12H22N2O8: d45 C12H22O: c337, e5 C12H22O2: d811, e172, m14 C12H22O3: h65 C12H22O4: d168, d384, d597, d787, d805 C12H22O6: d174

C12H22O11: L3, L4, m7, s20 C12H23N: d289 C12H23NO: a308, o47 C12H24: d813 C12H24Cl2: d224 C12H24O: c326, d817, e8, m459 C12H24O2: d809, e120 C12H24O6: c314 C12H25Br: b327 C12H25Cl: e119 C12H25Cl3Si: d821 C12H25I: i30 C12H25N: c340 C12H25N3: i6 C12H26: d803 C12H26O: d414, d810 C12H26O2: d806, d807 C12H26O3: b151 C12H26O4: d460, t91 C12H26O3S: d820 C12H26O5: t53 C12H26S: d808 C12H27Al: t322 C12H27B: t209 C12H27BO3: t207 C12H27ClSn: t213 C12H27N: d413, d818, t208 C12H27O3P: t212 C12H27O4P: t211 C12H28BrN: t130 C12H28N2: d804 C12H28O4Si: t129 C12H28O4Ti: t164, t165 C12H28Sn: t215 C12H29N: t323 C12H29N3: b196 C13 C13H6Cl2O2: h29 C13H8ClNO3: c198 C13H8Cl2O: d205 C13H8O: f3 C13H8OS: t162 C13H8O2: x3 C13H9BrO: b267 C13H9ClO: c56, c57 C13H9ClO2: c151 C3H9N: a60 C13H10: f2 C13H10ClNO: a140, a141, d745 C13H10Cl2: d221 C13H10Cl2O2: m243 C13H10F2: b195 C13H10N2: p91

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C13H10N2O3: a235 C13H10O: b53, x1 C13H10O2: b139, h103, m68, p92 C13H10O3: d435, d747, p154, r5 C13H10O4: t320 C13H10O5: t88 C13H11Br: b326 C13H11Cl: c116 C13H11N: b102 C13H11NO: a124, b5 C13H11NO3: p87 C13H12: d759 C13H12NO2: b112 C13H12N2: b54, d754 C13H12N2O: d775 C13H12N2S: d774, t141 C13H12N4O: d746, p89 C13H12N4S: d773 C13H12O: d760, h116, h117, m63, p76 C13H12O2: m320 C13H12O4: d32 C13H12S: b118 C13H13ClSi: c117 C13H13N: d761, m238, p93 C13H13NO2: t187 C13H13N3: d755 C13H14N2: d35, m249 C13H14N2O3: a59 C13H14N4O: d746 C13H15NO: i96 C13H16O3: e79 C13H16O4: d389 C13H17NO2: e82 C13H18O3: b117 C13H18O5: t267 C13H20: p115 C13H20O: i58, i59 C13H22ClN: b130 C13H22N2: d290 C13H22O3Si: b129 C13H24O2: e273, i86 C13H24O4: d337 C13H26: t265 C13H26N2: m246, t369 C13H26O: t263, t264 C13H26O2: e232, t262 C13H27Br: b433 C13H28: t261 C13H28O4: t431 C13H29Cl: c250 C13H29NO4: b176 C13H30OSn: t216

C14 C14H6Cl2O2: d193 C14H7ClO2: c41, c42 C14H8O2: a298 C14H8O4: d426 C14H9Br: b391 C14H9ClO3: c63 C14H9Cl5: b173 C14H9NO2: a108, a109 C14H10: a297, d742, p62 C14H10ClNO3: a144 C14H10Cl2O4: b168 C14H10Cl4: b169 C14H10N2O2: d36, d37, d38, d39 C14H10O2: b35 C14H10O3: b45, b64, x2 C14H10O4: b141, d69, b71a C14H10O4S2: d796 C14H11N: d741, p123 C14H11NOS: a50 C14H12: d415, s9 C14H12Cl2O: b170 C14H12N2O: b38 C14H12N2O2: b36 C14H12O: a34, d26, m145 C14H12O2: b46, b83, b84, b113, d740 C14H12O3: b37, b100, b125, h144 C14H13ClO: c169 C14H13N: e104, i9 C14H13NO: b82, d739 C14H13NO2: b50 C14H14: d752 C14H14N2: a168 C14H14N2O: m240 C14H14N2O3: a315 C14H14O: d73 C14H14OS: b223 C14H14O2: b114 C14H14O4: d33 C14H14S2: b222, d72 C14H15N: d71 C14H16N2O4: b207 C14H16O2Si: d503 C14H16O4: d340 C14H18N2O2: m132 C14H18O: p56 C14H18O4: d343 C14H18O7: p21 C14H19O3: d293 C14H22O: d160, d161, d162, d163

C14H22O2: d145 C14H22O3: d153 C14H22O4: h59 C14H22O6: t281 C14H22O7: t52 C14H23N: d142 C14H23N3O10: d299 C14H26O2: i87 C14H26O3: h10 C14H26O4: d152, d395, d459 C14H27ClO: t46 C14H28: t47 C14H28O: d822 C14H28O2: d815, e272, t44 C14H29Br: b423 C14H29O4: b156 C14H30: t43 C14H30O: t45 C14H30O2Sn: d136 C14H31N: d602 C14H32N2O4: t90 C14H32OSn: t214 C15 C15H10N2O2: m247 C15H10O2: b105, m136, p122 C15H11NO: d762 C15H11NO2: m128 C15H12N2O2: d756 C15H12O: c23 C15H12O2: d68 C15H13NO: a13 C15H14O: d767 C15H14O2: b49, d768, h169 C15H14O3: b116, m239 C15H16O: c316a C15H16O2: e189, i113 C15H17N: b96a C15H17N3: d797 C15H20O6: e184 C15H22O3: d117, e174 C15H22O5: o46 C15H23N: b583 C15H24: t327 C15H24O: d156 C15H26O6: g20 C15H28O2: d816, i112 C15H29N: p12 C15H30N2: t368 C15H30O: p13 C15H30O2: m428 C15H32: p11 C15H32O10: t409 C15H33NO6: t443

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15.

C16 C16H10: b52, f1, p255 C16H11NO2: p153 C16H12N4O9S2: t5 C16H13N: p132, p133 C16H14: d744, e71 C16H14O2: b93 C16H14O6S: s29 C16H16O2: b47 C16H16O3: d515 C16H18ClN3S: m248 C16H19ClSi: b537 C16H20N2: d74 C16H20N2O: b178 C16H20O2Si: d302 C16H22O4: d165, d410 C16H22O11: g9 C16H24N2: d150 C16H26O3: d814 C16H26O7: t54 C16H28O: c346 C16H30O2: d819 C16H30O4: b158, d157, d167, d360 C16H32: h37 C16H32O: e10 C16H32O2: h34 C16H33Br: b345 C16H33Cl: c148 C16H33I: i35 C16H33NO: d359 C16H34: h4, h31, h36 C16H34O: d729, h35 C16H34O2: h32 C16H34O4: b157 C16H34S: d720, h33 C16H35N: d728, h37 C16H35O3P: b192 C16H36BF4N: t25 C16H36BrN: t21 C16H36BrP: t29 C16H36Br3N: t26 C16H36ClN: t22 C16H36IN: t24 C16H36O4Si: t28 C16H36Sn: t30 C16H37NO4S: t23 C17 C17H12O3: p118, p119 C17H13N3O5S2: p173 C17H15N2O: d355

C17H16O4: d75, p194 C17H18N2O4: p193 C17H18O2: b589 C17H18O3: b592 C17H18O4: b203 C17H20N2O: b178 C17H20N4O6: r8 C17H21NO4: b291 C17H22N2: m245 C17H23NO3: a305 C17H24O6: b492 C17H25NO2: m15 C17H27NO2: e170 C17H28NO: d149 C17H28O7: d181 C17H34O2: m269a, i131 C17H34O4: b160 C17H36: h1 C17H36O: h1a C17H37N: m236 C18 C18H12: b6, b7 C18H12N5O6: d766 C18H14: t7, t8, t9 C18H14O8: d70 C18H15As: t412 C18H15B: t414 C18H15ClSn: c268, t425 C18H15N: t410 C18H15NO2: e116 C18H15N3Si: a310 C18H15OP: t421 C18H15O3P: t422 C18H15O4P: t419 C18H15P: t420 C18H15Sb: t411 C18H16OSn: t426 C18H16O2: b520, d280 C18H16Si: t423 C18H18O3: e81 C18H20N2O2: e152 C18H20O: b548 C18H20O2: b48 C18H22: b182 C18H26O6: e185 C18H30O: t210 C18H30O2: o7 C18H32N4O14: d364 C18H32O2: o1 C18H32O16: r1 C18H33ClO: o13 C18H34O2: o10, o11 C18H34O4: d143

C18H36: o8 C18H36O: e13, o12 C18H36O2: e157, o5 C18H37Br: b384 C18H37Cl: c203a C18H37Cl3Si: o17 C18H37I: i43 C18H37N: o9 C18H37NO: o2 C18H38: o3 C18H38O: o6 C18H38S: o4 C18H39ClSi: t315 C18H39N: o15, t313 C18H39O7P: t435 C18H40Si: t316 C19 C19H15Br: b440, t417 C19H15Cl: c267, t418 C19H16: t415 C19H16O: t416 C19H18BrP: m458 C19H19N7O6: f31 C19H20Br4O4: i110 C19H20O4: b88 C19H22N2O: c276 C19H30O5: m252 C19H31N: d24 C19H34ClN: b127 C19H36O2: m347 C19H37NO: o16 C19H38O2: i109, m346 C19H40: n89, t114 C20 C20H10Br2O5: d105 C20H12: b56, b57, d65 C20H12O5: f4 C20H14O4: d765, p66 C20H15Br: b439 C20H18O2Sn: t424 C20H19N3: b2 C20H20BrOP: h136 C20H32O5: d782 C20H24N2O2: q2 C20H26O4: d291 C20H27O3P: i90 C20H30O2: a1 C20H30O6: b184 C20H31N: d20 C20H34O4: b159 C20H36O2: e229

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C20H38O2: e230 C20H38O4: b187 C20H40: i2 C20H40O: o18 C20H42: i1 C21 to C23 C21H15NO: b143 C21H21N: t198 C21H21O4P: t452 C21H22N2O2: s10 C21H24O2: b144 C21H28N2O: b177 C21H36O: p14 C21H40O2: o14 C21H45N3O12Si3: t448 C22H23N3O9: a306 C22H26O: b181 C22H30O2S: t140 C22H34O4: b547, d463 C22H42O8: b152 C22H44O2: b581, i75 C22H46: d801 C22H46O: d802 C22H48N2: t27 C23H18BrO2P: c18

C23H26N2O4: b447 C23H42O2: b581a C24 to C29 C24H16N2O2: b218 C24H18: t413 C24H20BNa: t126 C24H20Sn: t128 C24H27NO2: e169 C24H38O4: b193, d374, d466, d466a C24H40O5: c275 C24H46O4: d725, d812 C24H50: t41 C24H51N: t406 C24H51O3P: t438 C24H54OSn2: b224 C25H30ClN3: c315 C25H34Cl6O4: b189 C25H48O4: d465 C26H26N2O2S: b153 C26H42O2: d138 C26H42O4: d464 C26H47O3P: d462 C26H46O8: t312 C26H50O4: b190

C27H42O: c274 C27H50ClN: b96 C28H31ClN2O3: r6 C28H32: t127 C28H50O8: t314 C28H54O6Sn: b601 C29H44O2: m244 C29H50O7: p20 C30 to C57 C30H43FO2P: e188 C30H46O2: e187 C30H50: s8 C30H58O4S: d295 C30H62: s7 C30H63O3P: t324 C32H64O4Sn: d178 C32H66: d823 C36H75O3P: d726 C39H74O6: g21 C40H82O6P2: b217 C42H82O4S: d727 C45H86O6: g25 C51H98O6: g24 C55H98O6P2: i111 C57H104O6: g23

TABLE 1.15 Physical Constants of Organic Compounds See also the special tables of polymers, rubbers, fats, oils, and waxes. Names of the compounds in the table starting on p. 1.76 are arranged alphabetically. Usually substitutive nomenclature is employed; exceptions generally involve ethers, sulfides, sulfones, and sulfoxides. Each compound is given a number within its letter classification; thus compound c209 is 3-chlorophenol. Section 1.1, Nomenclature of Organic Compounds, should be consulted to familiarize oneself with present nomenclature systems. Synonyms or Alternate Names are found at the bottom of each spread in their alphabetical listing; the number following the same refers to the numerical place of this compound in the table. For example, epichlorohydrin, c120, indicates that this compound is found listed under the name 1-chloro-2,3-epoxypropane. Formulas are presented in semistructural form when no ambiguity is possible. Complicated systems are drawn in complete structural form and located at the bottom of each page and keyed to the number of the entry. Beilstein Reference. In this column is found the reference to the volume and page numbers of the fourth edition of Beilstein, Handbuch der Organischen Chemie (Springer-Verlag, New York, 1918). Thus the entry 9, 202 refers to an entry in volume 9 appearing on page 202. When the volume number has a superscript attached, reference is made to the appropriate supplementary volume. For example, 122, 404 indicates that the compound will be found listed in the second supplement to volume 12 on page 404. The earliest Beilstein entry is listed. Supplementary information may be found in the supplements to the basic series; such coordinating references (series number, volume number, and page number of the main edition) along with the system number are found at the top of each odd-numbered page. Similarly, a back reference such as H93; E II 64; E III 190 in a volume of Supplementary Series IV means that previous items on this compound are found in the same volume of the

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TABLE 1.14 Empirical Formula Index of Organic Compounds (Continued) The alphanumeric designations are keyed to Table 1.15. C20H38O2: e230 C20H38O4: b187 C20H40: i2 C20H40O: o18 C20H42: i1 C21 to C23 C21H15NO: b143 C21H21N: t198 C21H21O4P: t452 C21H22N2O2: s10 C21H24O2: b144 C21H28N2O: b177 C21H36O: p14 C21H40O2: o14 C21H45N3O12Si3: t448 C22H23N3O9: a306 C22H26O: b181 C22H30O2S: t140 C22H34O4: b547, d463 C22H42O8: b152 C22H44O2: b581, i75 C22H46: d801 C22H46O: d802 C22H48N2: t27 C23H18BrO2P: c18

C23H26N2O4: b447 C23H42O2: b581a C24 to C29 C24H16N2O2: b218 C24H18: t413 C24H20BNa: t126 C24H20Sn: t128 C24H27NO2: e169 C24H38O4: b193, d374, d466, d466a C24H40O5: c275 C24H46O4: d725, d812 C24H50: t41 C24H51N: t406 C24H51O3P: t438 C24H54OSn2: b224 C25H30ClN3: c315 C25H34Cl6O4: b189 C25H48O4: d465 C26H26N2O2S: b153 C26H42O2: d138 C26H42O4: d464 C26H47O3P: d462 C26H46O8: t312 C26H50O4: b190

C27H42O: c274 C27H50ClN: b96 C28H31ClN2O3: r6 C28H32: t127 C28H50O8: t314 C28H54O6Sn: b601 C29H44O2: m244 C29H50O7: p20 C30 to C57 C30H43FO2P: e188 C30H46O2: e187 C30H50: s8 C30H58O4S: d295 C30H62: s7 C30H63O3P: t324 C32H64O4Sn: d178 C32H66: d823 C36H75O3P: d726 C39H74O6: g21 C40H82O6P2: b217 C42H82O4S: d727 C45H86O6: g25 C51H98O6: g24 C55H98O6P2: i111 C57H104O6: g23

TABLE 1.15 Physical Constants of Organic Compounds See also the special tables of polymers, rubbers, fats, oils, and waxes. Names of the compounds in the table starting on p. 1.76 are arranged alphabetically. Usually substitutive nomenclature is employed; exceptions generally involve ethers, sulfides, sulfones, and sulfoxides. Each compound is given a number within its letter classification; thus compound c209 is 3-chlorophenol. Section 1.1, Nomenclature of Organic Compounds, should be consulted to familiarize oneself with present nomenclature systems. Synonyms or Alternate Names are found at the bottom of each spread in their alphabetical listing; the number following the same refers to the numerical place of this compound in the table. For example, epichlorohydrin, c120, indicates that this compound is found listed under the name 1-chloro-2,3-epoxypropane. Formulas are presented in semistructural form when no ambiguity is possible. Complicated systems are drawn in complete structural form and located at the bottom of each page and keyed to the number of the entry. Beilstein Reference. In this column is found the reference to the volume and page numbers of the fourth edition of Beilstein, Handbuch der Organischen Chemie (Springer-Verlag, New York, 1918). Thus the entry 9, 202 refers to an entry in volume 9 appearing on page 202. When the volume number has a superscript attached, reference is made to the appropriate supplementary volume. For example, 122, 404 indicates that the compound will be found listed in the second supplement to volume 12 on page 404. The earliest Beilstein entry is listed. Supplementary information may be found in the supplements to the basic series; such coordinating references (series number, volume number, and page number of the main edition) along with the system number are found at the top of each odd-numbered page. Similarly, a back reference such as H93; E II 64; E III 190 in a volume of Supplementary Series IV means that previous items on this compound are found in the same volume of the

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Basic Series on page 93, of Supplementary Series II on page 64, and of Supplementary Series III on page 190. The absence of a back reference implies that the compound involved is described for the first time in the series concerned. Formula Weights are based on the International Atomic Weights of 1993 and are computed to the nearest hundredth when justified. The actual significant figures are given in the atomic weights of the individual elements; see Table 3.2. Density values are given at room temperature unless otherwise indicated by the superscript figure; thus 0.9711112 indicates a density of 0.9711 for the substance at 112⬚C. A density of 0.89916 4 indicates a density of 0.899 for the substance at 16⬚C relative to water at 4⬚C. Refractive Index, unless otherwise specified, is given for the sodium line at 589.6 nm. The temperature at which the measurement was made is indicated by the superscript figure; otherwise it is assumed to be room temperature. Melting Point is recorded in certain cases as 250 d and in some other cases as d 250, the distinction being made in this manner to indicate that the former is a melting point with decomposition at 250⬚C, while the latter decomposition occurs only at 250⬚C and higher temperatures. Where a value such as ⫺2H2O, 120 is given, it indicates a loss of 2 moles of water per formula weight of the compound at a temperature of 120⬚C. Boiling Point is given at atmospheric pressure (760 mmHg) unless otherwise indicated; thus 8215mm indicates that the boiling point is 82⬚C when the pressure is 15 mmHg. Also, subl 550 indicates that the compound sublimes at 550⬚C. Flash Point is given in degrees Celsius, usually using a closed cup. When the method is known, the acronym appears in parentheses after the value: closed cup (CC), Cleveland closed cup (CCC), open cup (OC), Tag closed cup (TCC), and Tag open cup (TOC). Because values will vary with the specific procedure employed, and many times the method was not stated, the values listed for the flash point should be considered only as indicative. See also Table 5.23, Properties of Combustible Mixtures in Air. Solubility is given in parts by weight (of the formula weight) per 100 parts by weight of the solvent and at room temperature. Other temperatures are indicated by the superscript. Another way in which solubility is explicitly stated is in weight (in grams) per 100 mL of the solvent. In the case of gases, the solubility is often expressed as 5 mL10, which indicates that at 10⬚C, 5 mL of the gas is soluble in 100 g (or 100 mL, if explicitly stated) of the solvent.

top of rh base of rh cap height base of text

Abbreviations Used in the Table abs, absolute acet, acetone alc, alcohol (ethanol usually) alk, alkali (aqueous NaOH or KOH) anhyd, anhydrous aq, aqueous, water as, asymmetrical atm, atmosphere BuOH, 1-butanol bz, benzene c, cold chl, chloroform conc, concentrated d, decomposes or decomposed D, dextrorotatory deliq, deliquescent dil, dilute diox, 1,4-dioxane DL, inactive (50% D and 50% L) DMF, dimethylformamide E, trans (German “entgegen”) EtOAc, ethyl acetate eth, diethyl ether EtOH, ethanol, 95%

expl, explodes glyc, glycerol h, hot HOAc, acetic acid hyd, hydrolysis hygr, hygroscopic i, insoluble ign, ignites i-PrOH, isopropyl alcohol, 2-propanol L, levorotatory m, meta configuration Me, methyl MeOH, methanol misc, miscible; soluble in all proportions NaOH, aqueous sodium hydroxide o, ortho configuration org, organic p, para configuration PE, petroleum ether pyr, pyridine s, soluble sec, secondary

sl, slight, slightly soln, solution solv, solvent subl, sublimes s, symmetrical sym, symmetrical tert, tertiary v, very v s, very soluble v sl s, very slightly soluble vac, vacuo or vacuum vols, volumes Z, cis (German “zusamman”) ⬎, greater than ⬍, less than ⬃, approximately ⫾, inactive [50% (⫹) and 50% (⫺)] ␣, alpha (first) position ␤, beta (second) position ␥, gamma (third) position ␦, delta (fourth) position ␻, omega position (farthest from parent functional group)

short standard long

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Solubility in 100 parts solvent

⫺38(CC) 40

i aq; s acet, alc, bz, chl, CS2, eth, dil alk i aq; 3.2 alc; 20 bz; 10 chl; 1.8 MeOH; 3.2 g in 100 mL HOAc i aq; v s alc, eth misc aq, alc, eth v s aq, alc, eth

1.76

a1

(⫺)-Abietic acid

302.46

92, 424

a2

Acenaphthene

154.21

5, 586

1.189

1.604895

a3 a4 a5

Acenaphthylene Acetaldehyde Acetaldoxime

CH3CHO CH3CH"NOH

152.20 44.05 59.07

5, 625 1, 594 1, 608

0.89916 4 0.78816 6 0.966

1.331620 1.41520

a6

Acetamide

CH3CONH2

59.07

22, 177

0.99978

1.4158110

a7 a8

CH3C("NH)NH2 ·HCl H2N(CO)CH2NHCH2CH2SO3H

94.54 182.20

2, 185

164–166 ⬎220 dec

CH3CONHC6H4CHO

163.18

14, 38

156–158

s aq, bz; sl s alc

CH3CONHC6H4SO3Cl

233.67

14, 702

148 dec

CH3CONHC6H4CO2H

179.18

14, 337

185–187

CH3CONHC6H4CO2H

179.18

14, 432

262 dec

d aq; v s alc, bz, eth, acet sl s aq; v s alc, bz, eth, acet i aq; s alc; sl s eth

223.28 190.16

12, 1331

H2NCOCH2N(CH2CO2H)2

192–196 219 d

a15 a16 a17 a18

Acetamidine HCl N-(2-Acetamido)-2aminoethanesulfonic acid 4-Acetamidobenzaldehyde 4-Acetamidobenzenesulfonyl chloride 2-Acetamidobenzoic acid 4-Acetamidobenzoic acid 2-Acetamidofluorene N-(2-Acetamido)iminodiacetic acid 2-Acetamidophenol 3-Acetamidophenol 4-Acetamidophenol Acetanilide

CH3CONHC6H4OH CH3CONHC6H4OH CH3CONHC6H4OH CH3CONHC6H5

151.17 151.17 151.17 135.17

13, 370 13, 415 13, 460 12, 237

1.29321 4 1.21915 4

207–210 146–149 170–172 114

a19 a20

Acetic acid Acetic acid-d

CH3CO2H CH3CO2D

60.05 61.06

2, 96 23, 202

1.049220 4 1.059

a9 a10 a11

a13 a14

279

88–91 ⫺123 46.5(␣) 12(␤) 81

280 21 114.5

16.7

222

70 aq; 50 alc; 16 pyr; s chl, glyc, hot bz v s aq; s alc; i acet, eth

i aq; s alc, glycols

304–305

173

118 115.5

39 (CC) 40

INTERACTIVE

1.371820 1.271520

93.4

LEFT

a12

172–175

(McGHP)

Flash point,⬚C

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

s alc, acet 0.56 aq25; 25 acet; 29 alc; 2 bz; 27 chl; 5 eth misc aq, alc, eth, CCl4 misc aq, alc, eth, CCl4

top of page

short standard

base of DF

CD3CO2D (CH3CO)2O

64.08 102.09

23, 203 2, 166

1.137 1.08015 4

a23 a24

Acetic anhydride-d6 Acetoacetanilide

(CD3CO)2O CH3COCH2CONHC6H5

108.14 177.20

12, 518

1.26020

a25 a26 a27 a28 a29

Acetoacetic acid Acetone Acetone-d6 Acetone oxime Acetonitrile

CH3COCH2COOH CH3COCH3 CD3COCD3 (CH3)2C"NOH CH3CN

102.09 58.08 64.13 73.10 41.05

3, 630 1, 635

a30 a31

Acetonitrile-d3 Acetophenone

CD3CN C6H5COCH3

a32

Acetophenonemethyl-d3

C6H5COCD3

⫺73

114.4 139

40 54 (CC)

85

6565mm dec

54 185

d viol 100 56 55.5 135 81.6

6

80.7 202

5 77

201–202

82

1.387520

1.359120 1.355420

1, 649 2, 183

0.790820 4 0.872 0.91162 2 0.787515 4

1.346015

36–37 ⫺94 ⫺93.8 60 ⫺44

44.08 120.15

24, 428 7, 271

0.844 1.02620 4

1.340620 1.537220

20

123.18

74, 626

1.055

1.532520

1.77

Acetamidoacetic acid, a46 2-Acetamidopentanedioic acid, a45 Acetoacetic ester, e58 Acetoin, h108 Acetonaphthones, m322, m323

ACES, a8 Acetal, d303 Acetaldehyde ammonia, a162 Acetaldehyde diethyl acetal, d303 Acetaldehyde dimethyl acetal, d504

1.368720 1.390420

⫺20 ⫺17

misc aq, alc, eth, CCl4 s chl, eth; slowly s aq forming HOAc, alc forming EtOAc see acetic anhydride s alc, hot bz, acids, alkalis, chl, eth misc aq, alc misc aq, alc, chl, DMF see acetone v s aq, alc, eth misc aq, acet, alc, chl, eth, EtOAc misc aq, alc, chl 0.55 aq; s alc, chl, eth, glyc

(McGHP)

Acetic-d3 acid-d Acetic anhydride

DEAN #37261

a21 a22

Acetonecarboxylic acid, a24 Acetone cyanohydrin, h138a Acetone dimethyl acetal, d519 Acetone ketal of glycerin, d599 Acetonylacetone, h60

RIGHT

a2

a3

INTERACTIVE

a1

a13

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short standard

base of DF

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No. a33

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

C6H5C6H4COCH3 CH3COBr

196.25 122.95

72, 337 2, 174

1.66316 4

1.448620

116–118 ⫺96

325–327 76

⬎110

CH3COCl

128.13 78.50

173, 5837 2, 173

1.184620 4 1.10420 4

1.458520 1.389620

⫺113

1075mm 51

⬎110 4 (CC)

758mm

72

2-Acetylbutyrolactone Acetyl chloride

a38

Acetylcholine bromide

(CH3)3N(Br)CH2CH2O2CCH3

226.11

41, 428

144–146

a39

Acetylcholine chloride

(CH3)3N(Cl)CH2CH2 O2CCH3

181.66

4, 281

150–152

a40

2-Acetylcyclopentanone Acetylene

126.16

7, 558

1.043

26.04

1, 228

0.90(g)

114.06

2, 801

62.04

2, 172

a43

Acetylenedicarboxylic acid Acetyl fluoride

HO2CC#CCO2H CH3OF

2-Acetylfuran N-Acetyl-(⫺)-glutamic acid

HO2CCH2CH2CHCO2CH3

a46

N-Acetylglycine

CH3CONHCH2CO2H

a47

1-Acetylimidazole

110.11 189.17

17, 286 42, 908

117.10

4, 354

⫺85(subl)

⫺18

180 d ⬍⫺60

1.00215 4 1.098

20

1.5065

29–30 200–201

20.8 10mm

67

1 vol in 1 vol aq, in 6 vol HOAc or alc; s bz, eth; acet dissolves 25 vol15 but 300 vols at 12 atm v s aq, alc, eth 5 aq(dec); sl s acet, alc, bz, eth

71

INTERACTIVE

a44 a45

1.490520

i aq; v s alc, acet dec viol by aq or alc; misc bz, chl, eth 20% v/v aq dec viol aq or alc; misc bz, chl, eth, HOAc, PE v s aq (dec by hot aq or alkalis); s alc; i eth v s aq, alc; dec by hot aq or alkalis; i eth

LEFT

a36 a37

(McGHP)

1.78

112, 186

HC#CH

Solubility in 100 parts solvent

⬎300

222.20

a34 a35

a42

Flash point,⬚C

CH3COC6H5SO3⫺ Na⫹

4-Acetylbenzenesulfonic acid, sodium salt Acetylbiphenyl Acetyl bromide

a41

Boiling point,⬚C

NHCOCH3

110.12

206–208

2.7 aq15; s alc; sl s acet, chl, HOAc; i bz, eth

103–105

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short standard

base of DF

a57 a58

2-Acetylthiophene 1-Acetyl-2-thiourea

a50 a51

169.95 195.69

2, 174 Merck: 12, 6003

C6H5CH(CN)COCH3

241.31 159.19

10, 699

(C5H4N)COCH3 (C5H4N)COCH3 (C5H4N)COCH3 HO2C6H4-2-O2CCH3

141.17 121.14 121.14 121.14 180.16

21, 21, 21, 10,

(C4H3S)COCH3 CH3C(O)NHC(S)NH2

126.18 118.16

17, 287 3, 191

1.79

p-Acetotoluide, m374 Acetoxime, a28 2-Acetoxybenzoic acid, a56 1-Acetoxy-1,3-butadiene, b378 (Acetoxymethyl)benzene, b76 3-Acetoxypropene, a74 Aceturic acid, a46

2.067420 4

1.549120

108

dec aq, alc; s bz, eth v s aq, alc, chl; i eth; dec by alkalis, eth

172–173 180–185

279 279 279 67

92–94 1.146 1.080 1.102 1.095 1.35

1.502620 1.520320 1.533620 1.535020

1.16822 4

1.556420

218 188–189 220 212 135

10–11 167

214

⬎110 73 150 ⬎110

v s alc, eth v s acids, alc, eth; s aq v s alc, eth 0.33 aq25; 29 acet; 20 alc; 5.9 chl; 5 eth; s bz sl s aq; misc alc, eth s hot aq, alc; sl s eth

(McGHP)

CH3COI CH3CO2CH(CH3)CH2⫺ N(Br)(CH3)3

a52 a53 a54 a55 a56

Acetyl iodide Acetyl-2-methylcholine chloride 2-Acetylphenothiazine 2-Acetylphenylacetonitrile 1-Acetyl-4-pipidone 2-Acetylpyridine 3-Acetylpyridine 4-Acetylpyridine Acetylsalicylic acid

DEAN #37261

a48 a49

Acetylene tetrabromide, t16 Acetylene tetrachloride, t37 N-Acetylethanolamine, h119 3-Acetyl-6-methyl-2H-pyran-2,4-(3H)-dione, d25 2-(Acetyloxy)benzoic acid, a56 3-Acetyl-1-propanol, h164 N-Acetylsulfanilyl chloride, a10

Acetylacetanilid, a24 Acetyl acetate, a22 Acetylacetone, p34 N-Acetylanthranilic acid, a11 Acetylbenzene, a31 Acetylcyclopropane, c410 Acetylene dichloride, d228, d229

RIGHT

a40

a44

a47

a50

INTERACTIVE

a36

a52

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short standard

base of DF

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

a59

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

246.27

222, 469

179.22

20, 459

1.00520 4

Acrylamide

H2C"CHCONH2

71.08

2, 400

1.22230 4

a62

Acrylic acid

H2C"CHCO2H

72.06

2, 397

1.051120

a63 a63a a64

Acrylonitrile Acryloyl chloride 1-Adamantanamine

H2C"CHCN H2C"CHCOCl

53.06 90.51 151.25

0.806020 4 1.114

a65

Adamantane

136.24

a66

Adenine

135.13

2, 400 2, 400 Merck: 12, 389 Merck: 12, 149 26, 420

a67 a68

(⫺)-Adenosine (⫾)-␣-Alanine

CH3CH(NH2)CO2H

267.24 89.09

31, 27 4, 387

1.424

a69

(⫺)-␣-Alanine

CH3CH(NH2)CO2H

89.09

4, 381

1.401

a70 a71 a72 a73

␤-Alanine Allantoin Allene Alloxan monohydrate

H2NCH2CH2CO2H

89.09 158.12 40.06 160.09

4, 401 25, 474 1, 248 24, 500

1.437⫺5

a74 a75 a76

Allyl acetate Allyl alcohol Allylamine

H2C"CHCH2OCOCH3 H2C"CHCH2OH H2C"CHCH2NH2

100.12 58.08 57.10

2, 136 2, 436 4, 205

Flash point,⬚C

206

s aq, alc; v s eth

106–110 subl 100 84.5

346

1.422420

12–14

141

50

1.391120 1.435020

⫺83.5

77.3 72–76

0 15

192.6

160–190 1.09

1.787

0.97720 4 0.854020 4 0.76120 4

1.568

270 (sealed tube) 360 dec 235 264–269 (depends on heating rate) dec 297

1.4168

1.404020 1.413420 1.418520

197 dec 238 ⫺136 anhyd: 256 dec ⫺129 ⫺88.2

Solubility in 100 parts solvent

s alc, eth, CS2, PE; sl s hot aq at 30⬚, g/100 mL: 215 aq, 155 MeOH, 86 EtOH, 63 acet, 12.6 EtOAc, 2.7 chl, 0.3 bz misc aq, alc, bz, eth, chl, acet 7.3 aq; misc org solv d aq; v s chl sl s aq

205 subl

s acet

subl 220

0.005 aq; sl s alc; i chl, eth s aq; i alc 16.7 aq25; 0.009 alc25; i eth

subl ⬎200

LEFT

H2C"C"CH2

Boiling point,⬚C

16.7 aq25; 0.2 alc25; i eth v s aq; sl s alc; i eth 0.45 aq; 0.2 alc; i eth

INTERACTIVE

a61

Melting point,⬚C

(McGHP)

1.80

a60

N-Acetyl-(⫾)-tryptophan Acridine

Refractive index

DEAN #37261

No.

⫺34

104 97 53–55

22 21 ⫺29

s aq, alc, acet, HOAc; sl s chl, EtOAc, PE i aq; misc alc, eth misc aq, alc, chl, eth misc aq, alc, chl, eth

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short standard

base of DF

N-Allylaniline Allylbenzene Allyl bromide Allyl butanoate

C6H5NHCH2CH"CH2 C6H5CH2CH"CH2 H2C"CHCH2Br CH3CH2CH2COOCH2CH"CH2

133.19 118.18 120.98 128.17

0.98225 0.89220 0 1.39820 4 0.902

12, 170 5, 484 1, 201 2, 272

1.563020 1.512220 1.465420 1.414220

⫺119 4415mm

Adipic acid, h54 Adipic acid monoethyl ester, e177 Adiponitrile, d284 Alaninol, a264, a265

1.81

a60

a59

89 33 ⫺2

i aq; s alc, eth i aq; s alc, eth sl s aq; misc org solv

Allocimene, d669 Allylacetone, h77 4-Allylanisole, a89 Allyl butyrate, a80

a64

a65

(McGHP)

Aconitic acid, p206 Acrolein, p203 Acrolein diethyl acetal, d312 Acrolein dimethyl acetal, d521 Acrylaldehyde, p203

220 157 70 41

DEAN #37261

a77 a78 a79 a80

a66

RIGHT

a71

INTERACTIVE

a67

a73

top of page

short standard

base of DF

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

Formula

Allyl chloride

H2C"CHCH2Cl

a82 a83 a84

Allyl chloroformate Allylcyclohexylamine 4-Allyl-1,2-dimethoxybenzene N-Allyl-N,N-dimethylamine Allyl ethyl ether Allyl iodide Allyl isothiocyanate Allyl methacrylate

H2C"CHCH2OOCCl (C6H11)NHCH2CH"CH2 H2C"CHCH2C6H3(OCH3)2

a85 a86 a87 a88 a89

H2C"CHCH2N(CH3)2

1.82

H2C"CHCH2OCH2CH3 H2C"CHCH2I H2C"CHCH2NCS H2C"C(CH3)COOCH2CH"CH2 H2C"CHCH2SCH3 H2C 9 CHCH2OCH2-

Beilstein reference

Density, g/mL

Refractive index

1, 198

0.93820 4

1.415420

⫺134.5

44–46

120.54 139.24 178.23

3, 12

1.136 0.962 1.036

1.4223 1.466420 1.534420

110

27 6612mm 255

6, 963

⫺4

1.401020

85.0 86.13 167.98 99.16 126.16

1, 438 1, 202 4, 214 23, 1290

0.76520 4 1.82520 4 1.01325 4 0.938

1.388120 1,554021 1.524825 1.4360

88.17 114.14

1, 440

0.803 0.962

132.16

1, 513

Flash point,⬚C

sl s aq; misc alc, chl, eth, PE

⫺20

i aq; misc alc, eth i aq; misc alc, eth 0.2 aq; misc org solv

64

46 33

1.471420 1.433220

91–93 154

18 57

1.068

1.462020

14228mm

⬎110

0.7830

1.407525

102

0

220 192 90–92

88 62 ⫺5

117.5 176740mm 66–67 84–88

31 21 ⫺1 7

a92

H2C"CHCH2⫺ CH2CH(OH)CH2OH H2C"CHCH2OSi(CH3)3

130.26

a94 a95 a96 a97

3-Alloxy-1,2-propanediol Allyloxytrimethylsilane 2-Allylphenol Allyl phenyl ether Allyl propyl ether 1-Allyl-2-thiourea

H2C"CHCH2C6H4OH H2C"CHCH2OC6H5 H2C"CHCH2OC3H7 H2C"CHCH2NHC(S)NH2

134.18 134.18 100.16 116.19

6, 572 6, 144 1, 438 4, 211

1.03315 4 0.98315 4 0.76720 4 1.21920 20

1.545020 1.520020 1.399020

a98 a99 a100 a101 a102

Allyltrichlorosilane Allyltriethoxysilane Allyl trifluoroacetate Allyltrimethylsilane Allylurea

H2C"CHCH2SiCl3 H2C"CHCH2Si(OC2H5)3 CF3COOCH2CH"CH2 H2C"CHCH2Si(CH3)3 H2C"CHCH2NHCONH2

175.52 204.34 154.09 114.27 100.12

43, 1909 43, 1909 24, 464

1.201120 4 0.903020 1.183 0.719320 4

1.455020 1.406220 1.335020 1.408020

4, 209

a103

Aminoacetonitrile

H2NCH2CN

56.07

4, 344

Solubility in 100 parts solvent

⫺31 (CC) 31 53

68 103 152 6143mm

Allyl methyl sulfide 1-Alloxy-2,3-epoxypropane

a93

Boiling point,⬚C

76.53

a90 a91

O

Melting point,⬚C

(McGHP)

a81

Formula weight

⫺99 ⫺80

CH " CH2

70–72

5815mm d

s alc, eth i aq; s alc, misc eth s alc; misc eth 3.3 aq; s alc; i bz; v sl s eth

INTERACTIVE

85

LEFT

10

v s aq, alc; i chl, CS2 eth, toluene s acids, alc

top of page

short standard

base of DF

a105 a106 a107

H2NCH2CN·H2SO4

154.14

4, 344

121

d 165

H2NC6H4COCH3

135.17

14, 41

H2NC6H4COCH3

135.17

14, 45

99

290

H2NC6H4COCH3

135.17

14, 46

106

293–295

223.23

14, 177

ca. 250

subl

223.23

14, 191

295 d

subl

109 128

⬎360 300 sl d

703mm

a110 a111

1-Aminoanthraquinone 2-Aminoanthraquinone 4-Aminoantipyrine p-Aminoazobenzene

203.25 197.24

24, 273

C6H5N"NC6H4NH2

a112

2-Aminobenzamide

H2NC6H4CONH2

136.15

14, 320

110

a113

4-Aminobenzenearsonic acid

H2NC6H4AsO(OH)2

217.06

16, 878

232

a114

5-Aminobenzene-1,3dicarboxylic acid

H2NC6H3(COOH)2

181.15

141, 636

⬎300

a109

1.83

v sl s aq; s alc, eth

s hot aq, alc, eth, HOAc; sl s bz i aq; v s alc, bz, chl, eth, HOAc, HCl i aq, eth; s alc, bz s aq, alc, bz; sl s eth sl a aq; v s alc, bz, chl, eth v s hot aq, alc; i bz; sl s eth s hot aq; alk CO3, conc⬘d mineral acids; i acet, bz, chl, eth

Aminoacetaldehyde diethyl acetal, d306 Aminoacetaldehyde dimethyl acetal, d506 1-Aminoadamantane, a64 Aminoanisoles, m48 thru m50 p-Aminoazobenzene, p88

Allyl mercaptan, p205 Allyl sulfide, d34 Allyl trichloride, t247 Aluminon, a306 N-Amidinosarcosine, c301

a109

INTERACTIVE

a108

⬎110

RIGHT

Allyl carbamide, a102 Allyl chloride, c236a Allyl cyanide, b482 Allyl glycidyl ether, a91 1-Allyl-2-hydroxybenzene, a94 Allyl iodide, i50

v s aq; sl s alc; i eth

(McGHP)

a108

Aminoacetonitrile hydrogen sulfate 2⬘-Aminoacetophenone 3⬘-Aminoacetophenone 4⬘Aminoacetophenone

DEAN #37261

a104

a110

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short standard

base of DF

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No. a115

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

2 aq15; sl s alc, MeOH

d 288

1 aq20; sl s hot MeOH; i alc, bz, eth v s hot aq, alc, eth v s hot aq, alc; s eth 0.59 aq; 12 alc; 2 eth; s EtOAc, HOAc s alc, eth s hot aq; v s alc, eth v s hot aq, alc, eth sl s aq; s alc, eth v s conc⬘d acids, alc, chl, eth

H2NC6H4SO3H

173.19

14, 688

H2NC6H4SO3H

173.19

14, 695

a118 a119 a120

H2NC6H4COOH H2NC6H4COOH H2NC6H4COOH

137.14 137.14 137.14

14, 310 14, 383 14, 418

a121 a122 a123 a124 a125

2-Aminobenzonitrile 3-Aminobenzonitrile 4-Aminobenzonitrile 2-Aminobenzophenone 2-Aminobenzothiazole

H2NC6H4CN H2NC6H4CN H2BC6H4CN H2NC6H4COC6H5

118.14 118.14 118.14 197.24 150.20

14, 322 14, 391 14, 425 14, 76 27, 182

a126

2-Aminobenzotrifluoride 3-Aminobenzotrifluoride 4-Aminobenzotrifluoride N-(4-Aminobenzoyl)glycine 2-Aminobiphenyl 4-Aminobiphenyl 2-Amino-5-bromobenzoic acid (⫾)-2-Aminobutanoic acid 3-Aminobutanoic acid 4-Aminobutanoic acid 2-Amino-1-butanol

H2NC6H4CF3

161.13

1212, 453

1.29025

H2NC6H4CF3

161.13

12, 870

H2NC6H4CF3

161.13

123, 2151

H2NC6H4CONHCH2COOH

194.19

142, 258

198–199

H2NC6H4C6H5 H2NC6H4C6H5 Br(NH2)C6H3COOH

169.23 169.23 216.03

12, 1317 12, 1318 14, 370

50–53 52–54 218–219

299 19115mm

CH3CH2CH(NH2)COOH

103.12

4, 408

304 d

subl ⬎300

H3CCH2CH(NH2)COOH H2NCH2CH2CH2COOH CH2CH2CH(NH2)CH2OH

103.12 103.12 89.14

4, 412 4, 413 4, 291

193–194 195 d ⫺2

176–178

a127 a128 a129

a133 a133a a134 a135

subl

49 53 85 108 132

268 288–290 dec 223–226 dec

⬎110 ⬎110

1.478525

34

175

55

1.290

1.480020

6

187

85

1.28327

1.481525

38

8312mm

86

0.94420 20

1.452120

i aq; s alc, bz, chi ⬎110 ⬎110

74 (OC)

sl s aq; s alc s hot aq, alc, eth s alc, bz, chl, eth, HOAc; v s acet 21 aq25, 0.18 hot alc; i eth 125 aq; i alc, eth v s aq; i org solv misc aq; s alc

INTERACTIVE

a130 a131 a132

144–146 172–174 187

1.5114 1.374

LEFT

14, 681

(McGHP)

⬎300

173.19

a117

1.84

1.5 aq15; v sl s alc, eth

H2NC6H4SO3H

1.69

Solubility in 100 parts solvent

ca. d 325

2-Aminobenzenesulfonic acid 3-Aminobenzenesulfonic acid 4-Aminobenzenesulfonic acid 2-Aminobenzoic acid 3-Aminobenzoic acid 4-Aminobenzoic acid

a116

Flash point,⬚C

top of page

short standard

base of DF

a137

a138

a140 a141 a142 a143 a144

1.85

a145 a146

a147

223, 3788

H2NC6H2(Cl)(SO2NH2)2

285.73

144, 2810

257–261

H2N(Cl)C6H3COOH

171.58

14, 365

231–233

H2N(Cl)C6H3COOH

171.58

14, 412

188 d

0.910

39–42

1

H2NC6H4COC6H4Cl

231.68

14 , 389

104

H2N(Cl)C6H3COC6H5

231.68

14, 79

98–100

H2N(Cl)C6H3CF3

195.57

123, 1921

H2N(Cl)C6H3CF3

195.57

H2N(Cl)C6H3COC6H4COOH

275.69

H2NC6H4⫺C6H4Cl

203.67

128–134

H2NC6H2(Cl)(OCH3)COOH

201.61

206 d

H2N(Cl)C6H3OH

143.57

13, 383

139–143

H2N(Cl)(C5H3N)

129.56

222, 332

135–138

1.386

1.506920

14810mm

⬎110

673mm

none ⬎110

36–38 14, 661

171–173

2-Aminobutane, b510 4-Aminobutyraldehyde diethyl acetal, d299 Aminobutyric acids, a133, a133a, a134

i aq; s alc, acet, bz, chl, HOAc

12811mm

␣-Aminocaproic acid, a182 ⑀-Aminocaproic acid, a183

INTERACTIVE

Aminobenzenethiol, a297 Aminobenzyl cyanide, a255 1-Aminobutane, b509

156.27

RIGHT

a148

(HNC5H9)(CH2)4NH2

(McGHP)

a139

3-(4-Aminobutyl)piperidine 4-Amino-6-chloro-1,3benzenedisulfonamide 2-Amino-4-chlorobenzoic acid 5-Amino-2-chlorobenzoic acid 2-Amino-4⬘-chlorobenzophenone 2-Amino-5-chlorobenzophenone 2-Amino-5-chlorobenzotrifluoride 5-Amino-2-chlorobenzotrifluoride 2-(3-Amino-4-chlorobenzoyl)benzoic acid 4-Amino-4⬘-chlorobiphenyl 4-Amino-5-chloro-2methoxybenzoic acid 2-Amino-4-chlorophenol 2-Amino-5-chloropyridine

DEAN #37261

a136

a125

top of page

short standard

base of DF

3-Aminocrotononitrile 1-[(2-Aminoethyl)amino]-2-propanol 5-Amino-2,3-dihydro1,4-phthalazinedione 2-Amino-4,6-dihydroxypyrimidine 4-Amino-2,6-dihydroxypyrimidine 2-Amino-3,3-dimethylbutane 2-Amino-4,6-dimethylpyridine 4-Amino-2,6-dimethylpyrimidine 6-Amino-1,3-dimethyluracil 5-Amino-2,6-dioxo1,2,3,6-tetrahydro4-pyrimidinecarboxylic acid ␣-Aminodiphenylmethane 2-Aminoethanesulfonic acid 2-Aminoethanethiol 1-Aminoethanol 2-Aminoethanol 2-(2-Aminoethoxy)ethanol 2-(2-Aminoethylamino)ethanol 1-[(2-Aminoethyl)amino]-2-propanol

a151 a152 a153 a154 a155

1.86

a156 a157 a158

a159 a160 a161 a162 a163 a164 a165 a166

CH3C(NH2)"CHCN CH3CH(OH)CH2NHCH2CH2NH2

Formula weight

Beilstein reference

Density, g/mL

Refractive index

0.983725 4

1.478825

Melting point,⬚C

82.11 118.18

3, 660

177.16

251, 698

319–320

127.10

24, 468

⬎300

127.10

24, 469

⬎300

(CH3)3CCH(NH2)CH3

101.19

4, 193

(CH3)2(NH2)(C5H2N)

122.17

Boiling point,⬚C

102–103

22, 435

63–64

235

123.16

242, 45

184–186

155.16

24, 471

295 d

171.11

25, 264

⬎300

(C6H5)2CHNH2

183.25

12, 1323

H2NCH2CH2SO3H

125.15

4, 528

d ca. 300

HSCH2CH2NH2 CH2CH(OH)NH2 H2NCH2CH2OH H2NCH2CH2OCH2CH2OH

77.14 61.08 61.08 105.14

4, 286 4, 274 43, 642

1.011725 4 1.048

1.453920

97–99 97 10.3

H2NCH2CH2NHCH2CH2OH

104.15

4, 286

1.030

CH3CH(OH)CH2NHCH2CH2NH2

118.18

Merck: 12, 458

0.983725 4

1.063522 4

1.413020

1.595020

Solubility in 100 parts solvent

11210mm

⫺20

0.755

Flash point,⬚C

34

1

156 aq; 18.9 alc

304

⬎110

sl s aq; s acids 5.45 aq12; 0.004 alc17

110 d 171 218–224

93

v s aq; s alc s aq; sl s eth misc aq, org solv

1.486120

240753mm

⬎110

v s aq, alc; sl s eth

1.473825

11210mm

INTERACTIVE

a149 a150

Formula

LEFT

Name

(McGHP)

No.

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

s acids

top of page

short standard

base of DF

a168 a169

a171

a172

H2NCH2CH2NHCH2CH2Si(OCH3)3

H2NCH2CH2OSO3H

1.441825

1.87

221, 642

98–100

141.15

4, 276

277 d

160.22

221, 636

118

281.01

Merck: 12, 176

194–195

130.19

273, 370

0.992

1.475520

a152

a170

1370.15mm

25.6

205

i aq, bz, chl, eth; s alc, acet, HCl

175

s aq, alc, bz, acet, acids

2-Aminoethanol, e29 1-(2-Aminoethyl)amino-2-[(2aminoethyl)aminoethyl]aminoethane, t56 Aminoethylbenzene, e69, e70

a157

a156

a171

INTERACTIVE

a168

a153

150

RIGHT

a151

14015mm

210.28

2-Amino-1,5-dihydro-1-methyl-4H-imidazol-4-one, c302 2-Aminodiphenylamine, p137 Aminodiphenylmethane, d761 Aminoethane, e63

4-Amino-m-cresol, a213 Aminocyclododecane, c340 Aminocyclohexane, c375 Aminodecane, d23 2-Amino-5-diethylaminopentane, d387

a158

1.0125 4

222.1

(McGHP)

a170

3-(2-Aminoethylamino)propyltrimethoxysilane 3-Amino-9-ethylcarbazole 2-Aminoethyl hydrogen sulfate 3-(2-Aminoethyl)indole S-2-Aminoethylisothiouronium bromide HBr N-(2-Aminoethyl)morpholine

DEAN #37261

a167

a172

top of page

short standard

base of DF

4-(2-Aminoethyl)phenol N-(2-Aminoethyl)piperazine N-(2-Aminoethyl)-1,3propanediamine 2-Amino-2-ethyl-1,3propanediol 2-(2-Aminoethyl)pyridine 4-(2-Aminoethyl)pyridine 2-Amino-5-fluorobenzotrifluoride Aminoguanidine hydrogen carbonate N-Aminohexamethyleneimine (⫾)-2-Aminohexanoic acid 6-Aminohexanoic acid 6-Amino-1-hexanol (⫺)-2-Amino-3hydroxybutanoic acid (⫾)-4-Amino-3hydroxybutanoic acid 4-Amino-6-hydroxy-2mercaptopyrimidine hydrate 2-Amino-4-hydroxy-6methylpyrimidine 4-Amino-3-hydroxy-1naphthalenesulfonic acid

a174 a175 a176 a177 a178 a179

1.88

a180 a181 a182 a183 a184 a185 a186 a187

a188 a189

HOC6H4CH2CH2NH2

Formula weight 137.18

Beilstein reference

Density, g/mL

Refractive index

13, 625

Melting point,⬚C 164–165

1662mm

⫺26

218–222

129.21

0.98520 20

1.498320

H2NCH2CH2CH2NHCH2CH2NH2 HOCH2C(NH2)(C2H5)CH2OH H2NCH2CH2(C5H4N)

117.20

0.928

1.481520

H2NCH2CH2(C5H4N)

122.17

H2N(F)C6H3CF3

179.12

123, 1991

H2NNHC("NH)NH2 ·H2CO3 (C6H12N)NH2

136.11

3, 117

CH3(CH2)3CH(NH2)COOH

131.17

4, 433

H2N(CH2)5COOH H2N(CH2)5CH2OH CH3CH(OH)CH(NH2)COOH H2NCH2CH(OH)CH2COOH

131.17 117.19 119.12

4, 434 42, 748 4, 514

204–206 56–58 d 255

119.12

42, 938

218 d

161.18

24, 476

⬎300

125.13

24, 343

⬎300

239.25

14, 846

295 d

Flash point,⬚C

93 (OC) 96 ⬎110

1.536020

9312mm

100

1.012

1.540320

1049mm

1.3781

1.460820

8120mm

4,3,850

1.09920 20

1.49020

122.17

22, 434

1.021

38

1.172

1.485020

misc aq; s alc

70

172 d 0.984

Solubility in 100 parts solvent 1 aq15; 10 boiling alc; s HCl

15210mm

119.16

114.19

Boiling point,⬚C

i aq; d hot aq 165

56 1.15 aq25; 0.42 alc25; s acids v s aq; i alc, s acids

301

13530mm v s aq; i alc, chl, eth s aq; sl s alc, chl, eth, EtOAc

INTERACTIVE

a173

Formula

LEFT

Name

(McGHP)

No.

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

i aq, alc, bz, eth

top of page

short standard

base of DF

a191

a192

a194 a195 a196

239.25

14, 835

sl s aq; i alc, eth

239.25

H2N(HO)(C5H3N)

1.89

2-(2-Aminoethyl)-2-thiopseudourea, a171 1-Aminoheptane, h19 2-Aminoheptane, m272 1-Aminohexane, h81

sl s hot aq; i eth

239.25

14, 849

⬎300

110.12

122, 408

172–174

111.10

24, 314

⬎300

133.19 133.19

12, 1191 121, 511

1.03815 4

2-Aminohexane, m371 p-Aminohippuric acid, a129 Aminohydroxybenzoic acids, a280, a281 2-Amino-2-(hydroxymethyl)-1,3-propanediol, t439

1.561320

0.77 aq; sl s alc 978mm 249745mm

1.5 36

(McGHP)

a193

4-Amino-5-hydroxy-1naphthalenesulfonic acid 5-Amino-6-hydroxy-2naphthalenesulfonic acid 6-Amino-7-hydroxy-2naphthalenesulfonic acid 2-Amino-3-hydroxypyridine 4-Amino-2-hydroxypyrimidine 1-Aminoindane 5-Aminoindane

DEAN #37261

a190

94 ⬎110

sl s aq sl s aq

␣-Amino-4-imidazolepropanoic acid, h83 Aminoiminomethanesulfinic acid, f34 N-(Aminoiminomethyl)-N-methylglycine, c301

RIGHT

a174

a192

a188

a194

a189

a195

a190

INTERACTIVE

a191

a187

a196

top of page

short standard

base of DF

5-Aminoindazole 6-Aminoindazole 2-Amino-5-iodobenzoic acid (⫾)-2-Amino-4-mercaptobutanoic acid Aminomethanesulfonic acid 3-Amino-4-methoxybenzoic acid 2-Amino-1-methoxypropane 5-Amino-2-methoxypyridine 4⬘-Amino-N-methylacetanilide 4-Amino-3-methylbenzenesulfonic acid 2-Amino-5-methylbenzoic acid 3-Amino-4-methylbenzoic acid 2-Amino-3-methyl-1butanol 2-(Aminomethyl)-1ethylpyrrolidine 2-Amino-3-methyl-1pentanol 2-Amino-4-methyl-1pentanol 4-Amino-3-methylphenol 4-(Aminomethyl)piperidine

a200 a201 a202 a203 a204

1.90

a205 a206 a207 a208 a209 a210 a211 a212 a213 a214

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

H2N(I)C6H3COOH

133.15 133.15 263.03

252, 308 25, 317 14, 373

175–178 206 d 221 d

HSCH2CH2CH(NH2)COOH

135.19

43, 1647

232–233

H2NCH2SO3H

111.12

1, 583

185 d

CH3O(NH2)C6H3COOH

167.16

141, 657

210

CH3OCH2CH(CH3)NH2

84.14

44, 1615

CH3O(NH2)(C5H3N)

124.14

222, 408

CH3ON(CH3)C6H4NH2

164.21

131, 30

90–92

H2NC6H3(CH3)SO3H

187.22

14, 726

⬎300

H2N(CH3)C6H3COOH

151.17

14, 481

175 d

sl s aq; s alc, eth

H2N(CH3)C6H3COOH

151.17

14, 487

167–169

s aq

(CH3)2CHCH(NH2)CH2OH

103.17

43, 805

128.22 CH2CH2CH(CH3)CH(NH2)CH2OH CH3CH(CH3)CH2CH(NH2)CH2OH H2N(CH3)C3H3OH

0.845

1.574520

0.906

1.454320

0.887

1.466520 1.458920

117.19 117.19

1.406520

4, 298

0.917

35–36

30

1.449620

123.16 114.19

31

sl s aq, PE; s alc

v s aq

93

8

901mm

⬎110

808mm

90

6016mm

60

9714mm

100

200

90

200

78

INTERACTIVE

a197 a198 a199

Formula

LEFT

Name

(McGHP)

No.

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

179 1.490020

25

top of page

short standard

base of DF

a216 a217 a218

a220 a221 a222 a223 a224

1.91

a225

HOCH2C(CH3)(NH2)CH2OH (CH3)2C(NH2)CH2OH

89.14

43, 783

(CH3)2C(NH2)COOH

103.12

4, 414

H2NCH2(C5H4N)

108.14

1.049

1.544020

H2NCH2(C5H4N)

108.14

1.062

1.551020

H2NCH2(C5H4N)

108.14

223, 4181

1.065

H2N(CH3)(C5H3N)

108.14

222, 342

1.073

H2N(CH3)(C4H3N)

108.14

H2N(CH3)(C4H3N)

0.93420 20

1.448020

15110mm

25

165

335 (sealed tube)

280 subl

250 aq20; s alc 67

90

⫺21

741mm

100

1.551520

⫺8

230

108

1.582320

32–34

222

111

222, 342

98–100

230

108.14

221, 633

42–45

209

109.13

24, 84

160

subl

114.17

27, 159

44–46

232

v s aq, alc, DMF 103

v s aq s hot aq; s alc

⬎110

v s aq, alc, eth

3-Amino-␣-methylbenzyl alcohol, a256 2-Amino-3-methylpentanoic acid, i88 2-Amino-2-methylpropane, b511

a214

a224

INTERACTIVE

a210

misc aq; s alc, org solv v s aq

8512mm

2-Amino-3-mercaptopropanoic acid, c411 1-Amino-2-methoxyethane, m77 ␣-(Aminomethyl)benzyl alcohol, a257

a198

108–110

RIGHT

2-Aminoisobutanol, a216 2-Aminoisobutyric acid, a217 5-Aminoisophthalic acid, a114

a197

105.14

(McGHP)

a219

2-Amino-2-methyl-1,3propanediol 2-Amino-2-methyl-1propanol 2-Amino-2-methylpropionic acid 2-(Aminomethyl)pyridine 3-(Aminomethyl)pyridine 4-(Aminomethyl)pyridine 2-Amino-3-methylpyridine 2-Amino-4-methylpyridine 2-Amino-6-methylpyridine 2-Amino-4-methylpyrimidine 2-Amino-4-methylthiazole

DEAN #37261

a215

a225

top of page

short standard

base of DF

2-Aminomethyl-3,5,5trimethylcyclohexanol N-Aminomorpholine 1-Aminonaphthalene 2-Aminonaphthalene 2-Amino-1-naphthalenesulfonic acid 5-Amino-2-naphthalenesulfonic acid 8-Amino-2-naphthol 2-Amino-4-nitrobenzoic acid 2-Amino-5-nitrobenzonitrile 5-Amino-5-nitrobenzophenone 2-Amino-6-nitrobenzothiazole 4-Amino-3-nitrobenzotrifluoride 2-Amino-4-nitrophenol 2-Amino-5-nitrophenol 4-Amino-2-nitrophenol D-(⫺)-threo-2-Amino1-(4-nitrophenyl)1,3-propanediol 2-Amino-5-(4-nitrophenylsulfonylthiazole 2-Amino-5-nitropyridine 2-Amino-5-nitrothiazole

a227 a228 a229 a230 a231 a232 a233

1.92

a234 a235 a236 a237 a238 a239 a240 a241

a242

a243 a244

Formula weight

Beilstein reference

171.29

Density, g/mL

Refractive index

0.969

1.490420

1.059 1.13

1.477220

Melting point,⬚C 43–48

Boiling point,⬚C

Flash point,⬚C

265

⬎110

168 301 306

58 157

Solubility in 100 parts solvent

(C10H7)NH2 (C10H7)NH2 H2N(C10H6)SO3H

102.14 143.18 143.18 223.25

27, 8 12, 1212 12, 1212 14, 736

H2N(C10H6)SO3H

223.25

14, 758

180

0.17 aq; v s alc, eth s hot aq, alc, eth 0.031 aq; sl s hot aq; s dil alkali sl s aq; s hot aq

H2NC10H6OH H2N(NO2)C6H3COOH

159.19 182.14

13, 685 14, 374

207 270 d

i aq; v s alc, eth

H2N(NO2)C6H3CN

163.14

142, 234

200–207

C6H5COC6H4(NH2)NO2

242.23

14, 79

166–168

195.20

272, 232

247–249

H2N(NO2)C6H3CF3

206.12

O2N(NH2)C6H3OH O2N(NH2)C6H3OH O2N(NH2)C6H3OH HOCH2C(NH2)C(OH)C6H4NO2

154.13 154.13 154.13 212.21

105–106 132, 192 13, 390 13, 520

285.30

H2N(C5H3N)NO2

48–50 111–113 dec

143–145 202 d 125–127 163–165

222–226

139.11

221, 631

186–188

sl s aq, bz, eth

145.14

Merck: 12, 477

d 202

s sl s aq; 0.7 alc; 0.4 ether; s dil acids

INTERACTIVE

a226

Formula

LEFT

Name

(McGHP)

No.

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

top of page

short standard

base of DF

123, 160

0.938

1.480720

4910mm

35

H(CH2)3CH(NH2)CH3 C2H5CH(NH2)C2H5 H(CH2)3CH(NH2)COOH

87.17 87.17 117.15

4, 177 4, 179 4, 416

0.73920 0.74920 4

1.404720 1.405520

91–92 91 320 subl

1

H2N(CH2)4COOH H2N(CH2)5OH H2NC6H4CH2CH2OH

117.15 103.17 137.18

4, 418 41, 441 133, 1679

12216mm 1484mm

65 ⬎112

H2NC6H4OH H2NC6H4OH

109.13 109.13

13, 354 13, 401

170–174 122–123

16411mm

13, 427

190

1503mm

45–48

312

a252 a253 a254

4-Aminophenol

H2NC6H4OH

109.13

a255

4⬘-Aminophenylacetonitrile 1-(3-Aminophenyl)ethanol 2-Amino-1-phenylethanol

H2NC6H4CH2CN

132.17

H2NC6H4CH(CH3)OH

137.18

133, 1654

68–71

H2NCH2CH(C6H5)OH

137.18

132, 361

56–58

a246 a247 a248 a249 a250 a251

a256

1.93

a257

1-Aminonaphthalene, n17 1-Amino-2-naphthol-4-sulfonic acid, a189

303

0.949 1.045

1.461520 1.584920

1-Amino-2-naphthol-6-sulfonic acid, a197 1-Aminoorotic acid, a158

158–161 35–37

16017mm

⬎110

s aq, alc, eth, PE misc aq, alc, eth 5.5 aq18; v sl s alc, chl, eth, PE v s aq; sl s alc; i eth

2 aq; 4.3 alc; v s eth 2.5 aq; v s hot aq, alc, eth 0.65 aq; 4.5 alc; 9.3 EtMeKetone58; s eth sl s hot aq; s alc

(McGHP)

111.19

exo-2-Aminonorbornane 2-Aminopentane 3-Aminopentane DL-2-Aminopentanoic acid 5-Aminopentanoic acid 5-Amino-1-pentanol 2-Aminophenethyl alcohol 2-Aminophenol 3-Aminophenol

DEAN #37261

a245

v s aq; s alc

1-Aminopentane, p53

RIGHT

a226

a242

a236

a244

INTERACTIVE

a227

a245

top of page

short standard

base of DF

1S,2S-(⫹)-2-Amino-1phenyl-1,3-propanediol L-2-Amino-3-phenyl1-propanol 3-Amino-1-phenyl-2pyrazolin-5-one N-Aminopiperidine 3-Amino-1,2-propanediol DL-1-Amino-2-propanol DL-2-Amino-1-propanol S-(⫹)-2-Amino-1-propanol 3-Amino-1-propanol 2-Amino-1-propene1,1,3-tricarbonitrile 3-Aminopropyl-(diethoxy)methylsilane 1-(3-Aminopropyl)imidazole N-(3-Aminopropyl)iminodiethanol N-(3-Aminopropyl)morpholine N-(3-Aminopropyl)-2pyrolidinone 3-Aminopropyltriethoxysilane 3-Aminopropyltrimethoxysilane 2-Aminopyridine

a259 a260 a261 a262 a263 a264

1.94

a265 a266 a267 a268 a269 a270 a271 a272 a273 a274 a275

Beilstein reference

Density, g/mL

Refractive index

C6H5CH(OH)CH(NH2)CH2OH

167.21

13,4, 2968

109–113

C6H5CH2(NH2)CH2OH

151.21

133, 1757

92–94

175.19 20, 89 4, 301

0.928 1.175

1.475020 1.492020

CH3CH(OH)CH2NH2

75.11

4, 289

0.973

1.448320

CH3CH(NH2)CH2OH

75.11

41, 432

0.943

CH3CH(NH2)CH2OH

75.11

43, 735

Solubility in 100 parts solvent

36 ⬎110

160

76

v s aq, alc; i eth

1.449520

173–176

83

v s aq, alc, eth

0.965

1.449820

176

62

v s aq, alc, eth

4, 288 Merck: 11, 495

0.982

1.461020

188

79 (TOC)

s aq, alc s aq

0.91620 4

1.42720

1.049

1.519020

162.23

0.1071

1.498020

144.22

0.987220 20

1.476120

142.20

1.014

1.50020

75.11 132.13

H2N(CH2)3Si(CH3)(OCH2CH3)2

191.4 125.18

H2N(CH2)3Si(OC2H5)3

221.37

H2N(CH2)3Si(OCH3)3

179.29

(C5H4N)NH2

Flash point,⬚C

146730mm 265739mm

H2NCH2CH2CH2OH NCC(CN)"C(NH2)CH2CN

H2N(CH3)N(CH2CH2OH)2

Boiling point,⬚C

210 d

100.17 91.11

H2NCH2CH(OH)CH2OH

Melting point,⬚C

94.12

233, 577

20 4

0.9506

10–12 171–173

888mm ⬎110

⫺15

20

1.4225 1.0125 4

22, 428

⫺2

1.42025 58.1

1702mm

137

224

98

1231mm

⬎110

217

104

808mm

83

210.6

92

misc aq, alc, bz

INTERACTIVE

a258

Formula weight

Formula

LEFT

Name

(McGHP)

No.

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

s aq, alc, bz, eth

top of page

short standard

base of DF

(C5H4N)NH2 (C5H4N)NH2

94.12 94.12 95.11 158.20

22, 431 22, 433 24, 80 22, 453

64 160–162 125–127 167–169

a280

4-Aminosalicylic acid

H2NC6H3(OH)CO2H

153.14

14, 579

150–151

a281 a282

5-Aminosalicylic acid 2-Aminoterephthalic acid 5-Amino-1,2,3,4-tetrazole hydrate

H2NC6H3(OH)CO2H H2NC6H3(CO2H)2

153.14 181.15

14, 579 14, 558

280 d 324 d

103.08

26, 403

204 d

a283

1-Aminopropane, p223 2-Aminopropane, i100 3-Amino-1-propene, a76 N-(3-Aminopropyl)diethanolamine, a270 6-Aminopurine, a66

4-Aminophenyl phenyl ether, p70 Aminophenyl sulfones, d47, d48 3-Aminophthalhydrazide, a151 5-Amino-m-phthalic acid, a114 Aminopicolines, a222, a223

250–252 273 subl 333

s aq, alc, bz, eth s aq, alc; sl s bz, eth v s aq sl s aq; v s alc, eth, acet; s hot bz 0.2 aq; 4.8 alc; s dil acids, alk; sl s eth

(McGHP)

3-Aminopyridine 4-Aminopyridine 2-Aminopyrimidine 4-Aminoquinaldine

DEAN #37261

a276 a277 a278 a279

2-Amino-3-pyridinol, a193 Aminopyrimidinediols, a152, a153 2-Aminosuccinamic acid, a301 Aminosuccinic acid, a304 6-Amino-2-thiouracil, a187

1.95

RIGHT

a260

a271

a269

a278

a279

INTERACTIVE

a272

a261

a283

top of page

short standard

base of DF

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Name

a284

2-Amino-1,3,4-thiadiazole 2-Aminothiazole

a285 a286 a287 a288

Formula

Formula weight

100.14

27, 155

93

H2NC6H4SH H2NC6H3(CH3)SO3H

100.14 125.19 187.22

27, 136 13, 397 14, 726

84.08 170.30

26, 137

H2N(C6H7)(CH3)3CH2NH2

129.59

a295 a296 a297

2-Anilinoethanol 3-Anilinopropionitrile Anthracene

C6H5NHCH2CH2OH C6H5NHCH2CH2CN

137.18 146.19 178.23

a298

9,10-Anthraquinone

1.96

Antipyrine

a300 a301

L-(⫹)-Arabinose L-(⫹)-Arginine

H2N(CH2)10CO2H C6H5NH2

0.922

1.488020

0.901

1.473320

201.31 93.12

208.20

H2NC("NH)NH(CH2)3CH(NH2)CO2H

1.642020

79–82 19–21 ⬎300 150–153 10

Flash point,⬚C

Solubility in 100 parts solvent

sl s aq, alc, eth; s hot aq, HCl s HCl 720.1mm

79 i aq12; v s hot aq s aq, alc, chl

247

⬎110

221

97

⫺6

184–186

70

198

245

193 (CC)

15210mm

190–192 12, 59

1.02720 20

Merck: 12, 696 12, 182

1.222 1.085

1.586320

1.579320

339–342

153 ⬎110 121 (CC)

185 (CC)

5, 657

1.2527 4

52–53 215-218

7, 781

1.4320 4

286

377

111–114

319

188.23

24, 27

150.13 174.20

31, 32 4, 420

113 4

1.088

157–160 d 240

3.5 aq25; s acids; misc most org solv 100 aq; v s alc sl s aq; v s alc, chl, eth 1.5 alc; 1.6 bz; 1.2 chl; 3.1 CS2; 0.5 eth; i aq 0.44 alc25; 0.6 chl20; 0.2 bz20; 0.11 eth25 100 aq; 77 alc; 100 chl; 2.3 eth 100 aq; 0.4 alc 15 aq21; sl s alc

INTERACTIVE

C6H5NH2 ·HCl

156.27

1.170

Boiling point,⬚C

LEFT

Aniline hydrochloride

a299

Melting point,⬚C 190–192

a294

a292

Refractive index

27, 624

a293

a291

Density, g/mL

101.13

2-Amino-2-thiazoline 2-Aminothiophenol 2-Aminotoluene-5-sulfonic acid 3-Amino-1,2,4-triazole 5-Amino-1,3,3-trimethylcyclohexanemethylamine 5-Amino-2,2,4-trimethylcyclopentanemethylamine 11-Aminoundecanoic acid Aniline

a289 a290

Beilstein reference

(McGHP)

No.

top of page

short standard

base of DF

L-(⫹)-Ascorbic

acid

a303

L-(⫹)-Asparagine

H2NCOCH2CH(NH2)CO2H

176.12

183, 3038

132.12

4, 476

1.6525

190–192

33 aq; 3.3 alc; 1 glyc; i bz, chl, eth, PE 3.5 aq28; s alkalis, acids; i alc, bz, eth

235

(McGHP)

Anisamide, m54 Anisic acids, m57, m58, m59 Anidisines, m48, m49, m50 Anisole, m55 p-Anisoyl chloride, m60 p-Anisyl alcohol, m61 Anthranilamide, a112 Anthranilic acid, a118 Araboascorbic acid, i61 APDC, p282 Arsanilic acids, a113

tert-Amylamine, d701 Amyl bromides, b325, b326 Amyl chloride, c204a ␣-Amylcinnamaldehyde, p56 Amyl ether, d738 Amyl iodide, i47 Amyl mercaptan, p37 Amyl methyl ketone, h14 Anethole, m107 Angelic acid, m169 Anilinesulfonic acids, a115, a116, a117 Anisaldehydes, m51, m52, m53

5-Amino-o-toluenesulfonic acid, a206 2-Amino-1,1,3-tricyanopropene, a267 1-Aminotricyclo[3.3.13,7]decane, a65 Aminouracil, a153 2-Aminovaleric acid, a248 5-Aminovaleric acid, a249 AMP, a216 Amyl compounds, see also Pentyl Amyl alcohol, p39 act-Amyl alcohol, m161 sec-Amyl alcohol, p40 tert-Amyl alcohol, m162

DEAN #37261

a302

1.97 a285

a299

a297

a291

a300

INTERACTIVE

a298

a289

a286

RIGHT

a284

a302

top of page

short standard

base of DF

DEAN #37261

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Name

a304

L-(⫹)-Aspartic

a305

a306

1.98

a307 a308 a309 a310 a311 a312 a313

Formula acid

HO2CCH2CH(NH2)CO2H

Formula weight

Beilstein reference

Density, g/mL

Refractive index

1.66112.5

Melting point,⬚C

Atropine

289.38

21, 27

114–116

Aurintricarboxylic acid, triammonium salt 2-Azacyclooctanone 2-Azacyclotridecanone Azidotrimethylsilane Azidotriphenylsilane 1-Aziridineethanol Azobenzene 2,2⬘-Azobis(2-methylpropionitrile)

473.44

102, 775

225 d

127.19 197.32 115.21 301.4 87.12 182.23 164.21

21, 242

35–38 150–153 ⫺95 83–84

16, 8 4, 563

116.08 258.28

3, 123 16, 637

225 d 120

128.17 128.09 337.86 106.12 121.13 197.24 228.29 228.29

52, 432 24, 467 13, 765 7, 174 9, 195 12, 262 5, 718 52, 628

1.22 1.05015 4 1.3414 1.315

99–100 252 d 250 d ⫺26 129–130 163 155–157 357 (Cu block) 5.5

(CH3)3SiN3 (C6H5)3SiN3 (C2H4N)CH2CH2OH C6H5N"NC6H5 (CH3)2C(CN)N"NC(CN)(CH3)2 H2NCON"NCONH2 H3OC6H4N"N( : O)C6H4OCH3

270–272

0.868

1.414020

1.088 1.20320 4

1.456020 67–68

a314 a315

Azodicarbonamide 4,4⬘-Azoxydianisole

a316 b1 b2 b3 b4 b5 b6 b7

Azulene Barbituric acid Basic fuchsin Benzaldehyde Benzamide Benzanilide 1,2-Benzanthracene 2,3-Benzanthracene

b8

Benzene

C6H6

78.11

5, 179

0.878715 4

1.501120

b9

Benzene-1,3,5-d3

C6H3D3

81.14

53, 518

0.908

1.499020

C6H5CHO C6H5CONH2 C6H5CONHC6H5

1.545620

1.35

0.45 aq; s alkalis, acids; i alc, eth 0.22 aq; 50 alc; 4 eth; 100 chl; 3.9 glyc; s bz, dil acids v s aq

subl 110 high vac

14810mm

⬎110

95–96 1000.01mm 168 293 107 d

23 67 4.2 alc20; s eth, HOAc 2 EtOH;20 5 MeOH;20 can explode in acetone i aq, alc; s hot aq

242

179 288–290 11710mm 437.6 subl

63

80.0

⫺11 (CC) ⫺11 (CC)

80

Solubility in 100 parts solvent

i aq; s org solvents s hot aq, dil acids 0.3 aq; s alc, acids 0.3 aq; misc alc, eth 1.3 aq; 17 alc; 30 pyr i aq; 1.7 alc; sl s eth sl s hot aq; s org solv sl s most org solv 0.17 aq; misc most org solv similar to ordinary benzene

INTERACTIVE

4, 472

Flash point,⬚C

LEFT

133.10

Boiling point,⬚C

(McGHP)

No.

top of page

short standard

base of DF

Benzene-13C6

13

b11

Benzene-d6

C6D6

b12

Benzenearsonic acid

C6H5AsO(OH)2

C6H6

84.07

0.949

1.501020

5.5

80

1.498620

6.8

79.1

84.16

53, 519

0.950

202.03

16, 868

1.76025

162

Azine, p257 Aziridine, e148 Azobis(isobutyronitrile), a313 Azole, p279 4,4⬘-Azoxyanisole, a315 Barbitol, d339

similar to ordinary benzene similar to ordinary benzene 2.5 aq; 2 alc; i chl

Behenyl alcohol, d817 Benzal bromide, d132 Benzal chloride, d273 Benzalphthalide, b105 Benzeneacetaldehyde, p77

(McGHP)

Aspirin, a56 Azabenzene, p257 Azacyclopentane, p280 Azacyclopropane, e146 1-Azanaphthalene, q3 Azelaic acid, n93

⫺11 (CC) ⫺11 (CC)

DEAN #37261

b10

1.99 b2

b6

a316

a308

INTERACTIVE

b1

a307

RIGHT

a306

a305

b7

top of page

short standard

base of DF

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

b13

Benzeneboronic acid

C6H5B(OH)2

121.94

16, 920

216

b14

1,4-Benzenedicarbaldehyde

C6H4(CHO)2

134.13

7, 675

113

248

b15

1,2-Benzenedicarbonyl dichloride 1,4-Benzenedicarbonyl dichloride 1,3-Benzenedicarboxylic acid 1,4-Benzenedicarboxylic acid 1,4-Benzenedimethanol Benzenehexacarboxylic acid Benzenesulfinic acid Benzenesulfonamide Benzenesulfonic acid

C6H4(COCl)2

203.02

9, 834

15–16

280–282

C6H4(COCl)2

203.02

9, 844

81

266

C6H4(COOH)2

166.13

9, 832

345–348

subl

9, 841

subl 402

Benzenesulfonyl chloride Benzenesulfonyl fluoride Benzenesulfonyl hydrazide 1,2,4,5-Benzenetetracarboxylic acid 1,2,4,5-Benzenetetracarboxyl dianhydride 1,2,3-Benzenetricarboxylic acid dihyrate

b16 b17 b18

1.100

b19 b20

b24 b25

b27 b28

1431mm

37 bz; 9 CCl4 0.012 aq; v s alc, HOAc; i bz, PE sl s alc; s alkalis; v sl s aq, chl, eth

C6H4(CH2OH)2

138.17

6, 919

C6(COOH)6

342.17

9, 1008

286 d

C6H5S("O)OH C6H5SO2NH2 C6H5SO2OH

142.16 157.19 158.18

11, 2 11, 39 11, 26

85 150–152 50–51

100 d

C6H5SO2Cl

176.62

11, 34

1.384215 15

1.551820

14.5

12010mm

⬎110

sl s aq; s alc, bz, eth i aq; sl s alc; s eth v s aq, alc; sl s bz; i CS2, eth i aq; s alc, eth

C6H5SO2F

160.17

112, 23

1.328620 4

1.492020

⫺5

207–208

87

s alc, eth

C6H5SO2NHNH2

172.21

11, 52

d 104

flammable solid

C6H2(COOH)4

254.15

9, 997

276

1.5 aq; v s alc

218.12

19, 196

283–286

246.18

9, 976

192 d

C6H3(COOH)3 ·2H2O

117–119

180

188 v s aq, alc

397–400

sl s aq; v s eth

INTERACTIVE

b29

1.100117

2.5 aq; 1.8 bz; 30 eth; 178 MeOH i aq; 6 bz; 17 acet; 2 eth; 14 diox; 46 MeOH d aq, alc; s eth

ROTATED

b26

166.13

Solubility in 100 parts solvent

LEFT

b21 b22 b23

C6H4(COOH)2

1.40920

Flash point,⬚C

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

C6H3(COOH)3

210.14

9, 997

231 d

C6H3(COOH)3

210.14

9, 978

⬎330

192.13

18, 468

161–163

24514mm

35–36

18016mm

b34 b35

1,2,4-Benzenetricarboxylic acid 1,3,5-Benzenetricarboxylic acid 1,2,4-Benzenetricarboxylic anhydride 1,3,5-Benzenetricarboxylic trichloride 1,2,4-Benzenetriol Benzil

141 95

346–348

b36

Benzil dioxime

b37

Benzilic acid

b38 b39 b40

Benzil monohydrazone Benzimidazole 7,8-Benzo-1,3-diazaspiro[4,5]decane2,4-dione 1,4-Benzodioxan

b31 b32 b33

1.101

b41

C6H3(COCl)3

265.48

C6H3(OH)3 C6H5CO9COC6H5

126.11 210.23

6, 1087 7, 747

C6H5C("NOH)C("NOH)C6H5 (C6H5)2C(OH)COOH

240.25

73, 3816

228.24

10, 342

C6H5C("NNH2)COC6H5

224.26 118.13 216.23

71, 394 23, 131 Merck: 12, 9372

136.15

50 acet; 22 EtOAc; 15 DMF ⬎110 v s aq, alc, eth, EtOAc i aq; s alc, bz, chl, EtOAc, eth i aq, HOAc, eth; sl s alc; s NaOH sl s aq; v s alc, eth hot aq

(␣) 240 (␤) 214 150 150–152 170.5 268

1.142

1.549020

⬎360

1036mm

1,4-Benzenediol, h86 Benzenemethanol, b78 1,2,3-Benzenetriol, t317 Benzenethiol, t156 Benzhydrazide, b71 Benzhydrol, d760 Benzhydrylamine, d761

sl s aq, eth; v s alc s alc, HOAc

87

Benzhydryl bromide, b326 p-Benzidine, b140 2-Benzimidazolethiol, m17 1,3-Benzodiazole, b39 1,2,3-Benzodioxaborole, c22 1,3-Benzodioxole, m251

RIGHT

Benzeneazobenzene, a312 Benzenecarbonitrile, b51 Benzenecarbonyl chloride, b66 Benzenecarboxyaldehyde, b3 Benzenecarboxylic acid, b44 Benzene-1,2-dicarboxylic acid, p168 Benzene-1,2-dicarboxylic anhydride, p169

1.2315 4

2.1 aq; 25.3 alc; 7.9 acet; v s eth sl s aq; v s alc; s eth

DEAN 37261 (McGHP)

b30

ROTATED

b32

b39

b40

b41

INTERACTIVE

b28

No.

Name

b42

2,3-Benzofuran

b43 b44

Benzofurazan-1-oxide Benzoic acid

b45

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index 1.566020

Flash point,⬚C

Solubility in 100 parts solvent

1.102

i aq; misc alc, bz, eth, PE

1.321

69–71 122.4

249

121 (CC)

9, 164

1.198915 4

42

360

110

212.25

8, 167

1.310020 4

137

19412mm

C6H5CH(C2H5)COC6H5 C6H5CH[OCH2CH(CH3)2]COC6H5 C6H5CH(OCH3)COC6H5 C6H5CH(OH)C("NOH)C6H5 C6H5CN

240.30 268.36

8, 174

1.101617 4 0.985

62

19520mm 1330.5mm

0.29 aq25; 43 alc; 10 bz; 22 chl; 33 eth; 33 acet; 30 CS2 i aq; s alc, acet, chl bz, HOAc, EtOAc s hot alc, acet; 20 pyr; sl s eth s alc, bz, eth

85

226.28 227.26

8, 174 8, 175

1.127814 4

48 152–156

18915mm

⬎110

v s alc, bz, eth sl s aq; s alc, NH4OH

103.12 202.26

9, 275 5, 718

1.010 1.27420 4

1.528920

⫺12.7 258

191 448

71

0.2 aq; misc org solv i aq; s alc, eth

C6H5COC6H5 C6H5C("NNH2)C6H5

182.22 196.25

7, 411 7, 417

1.110818 4

1.597545

48 95–98

305 23055mm

⬎110

13.3 alc; 17 eth; s chl

146.15

17, 327

55–60

252.32

Merck: 12, 1134 Merck: 12, 1105 7, 609

179

136.11 122.12

271, 740 9, 92

Benzoic anhydride

(C6H5CO)2O

226.22

b46

DL-Benzoin

C6H5COCH(OH)C6H5

b47 b48

Benzoin ethyl ether Benzoin isobutyl ether

b49 b50

Benzoin methyl ether ␣-Benzoinoxime

b51 b52

b56

Benzonitrile 1,2-Benzophenanthrene Benzophenone Benzophenone hydrazone 1-Benzopyran-4(4H)one 1,2-Benzo[a]pyrene

b57

4,5-Benzo[e]pyrene

b58

1,4-Benzoquinone

b59

Benzothiazole

135.19

b60

Benzo[b]thiophene

134.20

252.32 C6H4("O)2

108.10

Merck: 12, 1139 17, 59

1.572717 1.548520

1.31820 4

31210mm

s bz; sl s alc

179

s bz

116

1.246020 4

1.637920

2

13134mm

⬎110

sl s aq; s alc, hot bz, eth, hot PE; alkalis with dec sl s aq; v s alc, CS2

1.193740

1.630240

32

221

⬎110

s alc, bz, chl, eth

INTERACTIVE

C6H5COOH

ROTATED

56

1.072

LEFT

173–175

17, 54

b55

Boiling point,⬚C

⬍⫺18

118.13

b53 b54

Melting point,⬚C

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

1,2,3-Benzotriazole

b62 b63 b64 b65 b66

Benzoxazole 1-Benzoylacetone 2-Benzoylbenzoic acid Benzoyl bromide Benzoyl chloride

b67 b68 b69

Benzoyl cyanide Benzoyl fluoride Benzoylformic acid

119.13

26, 38

C6H5COCH2COCH3 C6H5COC6H4COOH C6H5COBr C6H5COCl

119.12 162.19 226.23 185.03 140.57

27, 42 7, 680 10, 747 9, 195 9, 182

C6H5COCN C6H5COF C6H5COCOOH

131.13 124.11 150.13

10, 659 9, 181 10, 654

1.238

1.642020

98.5

1.5594

30 60 129 ⫺24 ⫺1.0

1.09060 60 1.546720 1.21120 4

1.588320 1.553720

1.106 1.140

1.496020

32 ⫺28 67–69

Benzo[def]phenanthrene, p255 Benzopyridine, q3 Benzoresorcinol, d443 2-Benzothiazolethiol, m19 Benzotrichloride, t251

Benzofuroxan, b43 Benzoglyoxaline, b39 Benzoic acid hydrazide, b71 Benzhydroxylamine, a159 o-Benzoic sulfimide, s1

204 may explode 182 260 sl d 265 219 197.2

90 88 (CC)

206 161

48

58

sl s aq; s alc, bz, chl, DMF sl s aq sl s aq; v s alc, eth sl s aq; v s alc, eth d aq, alc; misc eth d aq, alc; misc bz, eth CS2 i aq d hot aq; v s alc, eth

DEAN 37261 (McGHP)

b61

Benzotrifluoride, t311 Benzoylamide, b4 Benzoylbenzene, b53 Benzoyl peroxide, d69 1,2-Benzophenanthrene, b6

1.103 b52

b43

b55

b56

RIGHT

b42

ROTATED

b57

b59

b61

b62

INTERACTIVE

b60

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

1.104

C6H5CONHCH2COOH

179.18

9, 225

179

b71 b71a b72

Benzoylhydrazine Benzoyl peroxide 3-Benzoylpropanoic acid 2-Benzoylpyridine 3-Benzoylpyridine 4-Benzoylpyridine Benzyl acetate Benzyl acetoacetate Benzylacetone Benzyl alcohol

C6H5CONHNH2 (C6H5CO)2O2 C6H5COCH2CH2COOH

136.15 242.23 178.19

9, 319 9, 179 10, 696

117 103–106 117–119

C6H5CO(C5H4N) C6H5CO(C5H4N) C6H5CO(C5H4N) CH3CO2CH2C6H5 CH3COCH2CO2CH2C6H5 C6H5CH2CH2COCH3 C6H5CH2OH

183.21 183.21 183.21 150.18 192.21 148.21 108.14

21, 330 21, 331 21, 331 6, 435 6, 438 7, 314 6, 428

44 40 71 ⫺51.5

Benzylamine N-Benzylaminoethanol 3-(Benzylamino)propanonitrile N-Benzylbenzamide Benzyl benzoate 2-Benzylbenzoic acid

C6H5CH2NH2 C6H5CH2NHCH2CH2OH C6H5CH2NHCH2CH2CN

107.16 151.21 160.22

C6H5CH2NHCH2C6H5 C6H5CO2CH2C6H5 C6H5CH2C6H4COOH

Benzyl bromide Benzyl 2-bromoacetate Benzyl-tert-butanol Benzyl butyl 1,2phthalate Benzyl carbamate Benzyl chloride

b73 b74 b75 b76 b77 b77a b78 b79 b80 b81 b82 b83 b84 b85 b86 b87 b88 b89 b90

1.05025 4 1.112 0.989 1.045320 4

1.499825 1.512120 1.512220 1.540320

12, 1013 12, 1040

0.98319 4 1.065 1.024

1.540120 1.543520 1.530820

211.26 212.25 212.24

9, 121 92, 471

1.11825 4

1.568121

C6H5CH2Br BrCH2CO2CH2C6H5 C6H5CH2CH2C(CH3)2OH C6H5CH2O2C6H4CO2C4H9

171.04 229.08 164.25 312.37

5, 306 61, 220 6, 548 92, 594

1.438022 0 1.446 1.11925 25

1.575220 1.544020 1.509020 1.540020

C6H5CH2OCONH2 C6H5CH2Cl

151.17 126.59

6, 437 5, 292

1.10020 20

1.538120

⫺15.2 10

106 21 110–113 ⫺3.9 31–33

87–89 ⫺43 to ⫺49

Solubility in 100 parts solvent 0.4 aq; 0.1 chl; 0.25 eth; sl s alc; i bz, PE

explodes

2.5 CS2; s bz, chl, eth sl s aq; s alc

317 397 315 213.5 15910mm 235 205

150 150 150 102 (CC) ⬎110 98 93 (CC)

185 15612mm

60 ⬎110 ⬎110

323

148

199 17022mm 14485mm

86 ⬎110 ⬎110 199

220 d 179

67

s alc, bz, eth s alc, bz, eth i aq; misc alc, eth

0.08 aq; misc alc, chl, eth misc aq, alc, eth

misc alc, chl, eth sl s aq; s alc, bz, chl, eth slowly dec aq

v s alc; sl s eth misc alc, chl, eth

ROTATED

N-Benzoylglycine

Flash point,⬚C

RIGHT

b70

Boiling point,⬚C

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

INTERACTIVE

b93 b94 b95

Benzyl chloroformate Benzyl chlorothiolformate Benzyl cinnamate S-Benzyl-L-cysteine

C6H5CH2OCOCl C6H5CH2SCOCl

170.60 186.5

6, 437

C6H5CH"CHCO2CH2C6H5 C6H5CH2SCH2CH(NH2)COOH (CH3)2NCS2CH2C6H5

238.29 211.28

9, 584 6, 465

1.195 1.23730 4

39 214 d

C6H5CH2N[(CH2)17CH3](CH3)2Cl·H2O

442.18

123, 2212

b96a b97

Benzyl N,N-dimethyldithiocarbamate Benzyldimethylstearylammonium chloride hydrate N-Butyl-N-ethylaniline Benzyl ethyl ether

C6H5N(CH2C6H5)C2H5 C6H5CH2OC2H5

211.31 136.20

b98 b99

N-Benzylformamide Benzyl formate

C6H5CH2NHCHO C6H5CH2O2CH

135.17 136.15

b100

Benzyl 4-hydroxybenzoate O-Benzylhydroxylamine hydrochloride Benzylidineaniline Benzylidenemalononitrile N-Benzylidenemethylamine

HOC6H4CO2CH2C6H5

228.25

12, 1026 Merck: 12, 1168 12, 1043 Merck: 12, 1169 10,3, 311

C6H5CH2ONH2 ·HCl

159.62

6, 440

C6H5N"CHC6H5 C6H5CH"C(CN)2

181.24 154.17

12, 195 9, 895

1.04550 4

C6H5CH"NCH3

119.17

7, 213

0.967

b96

1.105

b101

b102 b103 b104

211.35

10320mm 800.13mm

91 118

dec aq; s eth

2005mm

⬎110

s alc, eth; i aq, glyc

⬎110

41

Benzyl ethanoate, b76 N-Benzylethanolamine, b80 Benzyl ether, d73

67–69

1.029 0.947820

1.595020 1.495520

1646mm 186

⬎110 misc alc, eth; i aq

61 1.08120 4

203

i aq; s alc

110–112

56 83–85 1.552020

238 subl

⬎110

300

⬎110

8018mm

⬎112

Benzylideneacetone, p94 Benzylideneacetophenone, c23 Benzylidene chloride, d273

s alc, chl, CS2

RIGHT ROTATED

Benzylaniline, p93 Benzylbenzene, d759 Benzyl cyanide, p82 Benzyl disulfide, d72

1.519020 1.571130

DEAN 37261 (McGHP)

b91 b92

INTERACTIVE

b105

3-Benzylidenephthalide Benzyl mercaptan Benzyl methacrylate N-Benzylmethylamine 3-(N-Benzyl-N-methylamino)-1,2-propanediol Benzyl methyl sulfide 1-Benzyl-3-methyl-2thiourea Benzyl nicotinate 4-Benzyloxybenzaldehyde 4-Benzyloxybenzyl alcohol 2-Benzyloxyethanol 4-Benzyloxy-3-methoxybenzaldehyde 4-(Benzyloxymethyl)2,2-dimethyl-1,3dioxolane Benzyl phenyl sulfide 1-Benzylpiperazine 4-Benzylpiperidine 1-Benzyl-4-piperidone 2-Benzylpyridine 4-Benzylpyridine 1-Benzyl-2-pyrrolidinone Benzyl salicylate

b106 b107 b108 b109

b110 b111 b112 b113

1.106

b114 b115 b116 b117

b118 b119 b120 b121 b122 b123 b124 b125

Benzyl thiocyanate Benzyltributylammonium chloride

Formula weight

Beilstein reference

Density, g/mL

Refractive index

124.21

17, 376

C6H5CH2SH H2C"C(CH3)CO2CH2C6H5 C6H5CH2NHCH3 C6H5CH2N(CH3)CH2CH(OH)CH2OH

222.24 176.22 138.23 195.26

6, 453 63, 1481 12, 1019

1.05820 1.040 0.939 1.084

1.575120 1.512020 1.523020 1.534120

C6H5CH2SCH3 C6H5CH2NHC("S)NHCH3

138.23 180.27

6, 453 12, 1052

1.015

1.562020

(C5H4N)CO2CH2C6H5 C6H5CH2OC6H4CHO

213.24 212.25

22,3, 366 8, 73

1.165

C6H5CH2OC6H4CH2OH

214.26

C6H5CH2OCH2CH2OH C6H5CH2OC6H4(OCH3)CHO

152.20 242.29

62, 413

222.28

192, 73

200.30 176.26 175.28 189.26 169.23 169.23 175.23

6, 454

HOC6H4CO2CH2C6H5

228.25

C6H5CH2SCN C6H5CH2N(C4H9)⫹3 Cl⫺

149.22 312.94

Merck: 12, 1181 6, 460

C6H5CH2SC6H5

C6H5CH2(C5H4N) C6H5CH2(C5H4N)

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

99–102 20630mm 984mm 184–189 20630mm

⬎110 77 77 ⬎110

195–198

73

18912mm

⬎110

265

129

910.1mm

⬎110

41–44

19727mm

6–7

279 1347mm 276 287

⬎110 ⬎110 ⬎110 ⬎110 125 115 ⬎110

74–76 1.570020

21–23 73–74 86–87

1.0720 20

1.521020

0.4 aq

63–65

20, 296 20, 425 20, 426

1.051

1.494020

1.014 0.997 1.021 1.054 1.06120 0 1.095

1.546720 1.537920 1.539920 1.579020 1.581820 1.552520

8–10

1.17520

20825mm 43 164 d

235

i aq; sl s alc; s eth s aq, alc, eth

i aq; v s alc, eth s alc; v s eth

sl s aq; misc alc, eth ⬎110

i aq; s alc; v s eth

INTERACTIVE

b126 b127

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

b131 b132 b133

Benzyltrichlorosilane Benzyltriethoxysilane Benzyltriethylammonium chloride Benzyltrimethylammonium chloride Benzyltrimethylsilane Betaine

C6H5CH2SiCl3 C6H5CH2Si(OC2H5)3 C6H5CH2N(C2H5)⫹3 Cl⫺

1.28820 4 0.98620 4

1.525020

142100mm 17570mm

225.28 254.40 227.78

16, 912 12, 1021

185 d

C6H5CH2N(CH3)3 Cl

185.70

12, 1021

239 d

C6H5CH2Si(CH3)3 (CH3)3N⫹CH2COO⫺

164.32 117.15

16,1, 526 4, 347

⫹

Benzyl methyl ketone, p147 Benzyloxyamine, b101

⫺

0.893320

none

1.494120

190 dec 310

Benzylphenol, h116 o,o-Bibenzoic acid, b141

93

57 160 aq; 55 MeOH; 8.7 EtOH

DEAN 37261 (McGHP)

b128 b129 b130

Bibenzyl, d752 Bicine, b199

1.107 b117

b119

RIGHT

b105

ROTATED

b121

b124

INTERACTIVE

b120

No.

Name

b134

Bicyclo[2.2.1]hepta2,5-diene Bicyclo[2.2.1]-2-heptene Bicyclo[2.2.1]-2-heptene-2-carbaldehyde Biguanide

b135 b136 b137 b138 b139

1.108

b140 b141 b142 b143

b145

b147

b148 b149

Beilstein reference

92.14

Density, g/mL

Refractive index

0.90920

1.470720

94.16 122.16

1.108

Melting point,⬚C

⫺11

i aq; s PE

44–46

96

⫺15

s eth

7012mm

51

101.11

3, 93

154.20 198.22

5, 578 9, 671

H2NC6H4 9C6H4NH2 HOOCC6H4 9C6H4COOH

184.24 242.23

13, 214 9, 922

C6H5 9C6H4SO3H

234.26

138

226.28

30–32

H2C"CHCH2OC6H4C(CH3)2C6H4 9OCH2CH"CH2 H2N(CH2)3NHCH2CH2NH(CH2)3NH2

308.42

1.022

1.563620

174.29

0.952

1.491020

200.33

232, 12

0.973

1.501520

H2N(CH2)3NHCH2CH2CH2NH(CH2)3NH2

188.32

44, 1278

0.920

1.491520

BrCH2CH2OCH2CH2Br

231.92

[BrCH2Si(CH3)2]2O

320.17

130

dec 142

69–71 226

256 subl

120 228–229

ca. 400

1.471920

s aq, alc; i bz, chl, eth 113 (CC)

s alc; 2 eth; 20 hot alc 0.06 aq; s org solvents

⬎110

15

i aq; s alc, eth v s alc, eth; s bz; i aq

1200.1mm

1605mm

⬎110

1522mm

162

1031mm

10720mm 1.391820 4

Solubility in 100 parts solvent

89

1.488320

1.58877

Flash point,⬚C

⫺20

H2NC("NH)NHC("NH)NH2 C6H5 9C6H5 C6H5 9C6H4COOH

0.99175 4

Boiling point,⬚C

ROTATED

b146

Formula weight

LEFT

b144

10415mm

INTERACTIVE

Biphenyl 4-Biphenylcarboxylic acid 4,4⬘-Biphenyldiamine 2,2⬘-Biphenyldicarboxylic acid 4-Biphenylsulfonic acid 2-Biphenylyl glycidyl ether 2,2-Bis[4-(allyloxy)phenyl]-propane N,N⬘-Bis(3-aminopropyl)ethylenediamine N,N⬘-Bis(3-aminopropyl)piperazine N,N⬘-Bis(3-aminopropyl)-1,3-propanediamine Bis(2-bromoethyl) ether 1,3-Bis(bromoethyl)tetramethyldisiloxane

Formula

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

b151

b152 b153

b154 b155 b156

2,2-Bis(bromomethyl)1,3-propanediol Bis(2-butoxyethyl)ether

HOCH2CH(CH2Br)2CH2OH

261.95

(C4H9OCH2CH2)2O

218.34

Bis[2-(2-butoxyethoxy)ethyl] adipate 2,5-Bis(5-tert-butyl-22⬘-benzoxazolyl)thiophene Bis(sec-butyl) disulfide Bis(tert-butyl) disulfide 1,1-Bis(tert-butylperoxy)cyclohexane

[-CH2CH2CO2(CH2CH2O)2(CH2)3CH3]2

434.58

11, 251

23, 1718

114 0.885320 20

1.424020

⫺60.2

1.010

1.448020

⫺11

430.57

[CH3CH2CH(CH3)]2S2 (CH3)3CSSC(CH3)3

178.36 178.36

C6H10[OOC(CH3)3]2

260.38

1.109

Bicyclo[4.4.0]decane, d2, d3 Bicyclo[5.3.0]decapentane, a316 Biformyl, g28 Biphenol, d436

256

118

0.3 aq; misc alc, esters, eth, CCl4 ketones

110

201

13, 1549 1, 379

0.957 0.909

1.492020 1.493020

164739mm 204

112 79

0.970

1.457020

5415mm

90

Biphenylamines, a130, a131 2,2⬘-Bipyridine, d790 Bis(2-aminoethyl)amine, d362 Bis(4-aminophenyl)ether, o67

DEAN 37261 (McGHP)

b150

1,3-Bis(aminomethyl)cyclohexane, c349 1,2-Bis(benzylamino)ethane, d74 Bis(3-tert-butyl-4-hydroxy-5-ethylphenyl) sulfide, t140

RIGHT

b134

b135

b136

b143

ROTATED

b153

INTERACTIVE

b146

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

2,5-Bis(tert-butylperoxy)-2,5-dimethylhexane 2,5-Bis(tert-butylperoxy)-2,5-dimethyl3-hexyne Bis[1-(tert-butylperoxy)-1-methylethylbenzene 1,1-Bis(tert-butylperoxy)-3,3,5-trimethyl-cyclohexane 1,2-Bis(2-chloroethoxy)ethane Bis(2-chloroethoxy)methylsilane Bis(2-chloroethyl) ether Bis(2-chloroethyl)-Nmethylamine Bis(chloromethyl)dimethylsilane Bis(chloromethyl) ether Bis(2-chloro-1methyl)ethyl ether 1,3-Bis(chloromethyl)tetramethyldisiloxane Bis(4-chlorophenoxy)acetic acid

b158

b159

b160

1.110

b161 b162 b163 b164 b165 b165a b166 b167

b168

Formula weight

Beilstein reference

Density, g/mL

Refractive index

0.877

1.423020

577mm

41

0.881

1.432020

672mm

85

[(CH3)3COOC(CH3)2CH2-]2

290.45

(CH3)3COOC(CH3)2C#CC(CH3)2OOC(CH3)3

286.41

C6H4[C(CH3)2OOC(CH3)3]2

338.49

[(CH3)3COO]2C6H7(CH3)3

302.46

(ClCH2CH2OCH2-)2

187.07

H(CH3)Si(OCH2CH2Cl)2

203.1

ClCH2CH2OCH2CH2Cl

143.01

CH3N(CH2CH2Cl)2

156.07

(CH3)2Si(CH2Cl)2

157.12

43, 1845

1.97520 4

1.460020

ClCH2OCH2Cl

114.96

Merck: 12, 3119

1.31520 4

1.4346

ClCH2CH(CH3)OCH(CH3)CH2Cl [ClCH2Si(CH3)2]2O

171.07

(ClC6H4O)2CHCOOH

313.14

231.3

14, 2701

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

44–48

13, 2079

12, 335

1.441020

1.19720 4

1.461020

235

1.164320 4

1.443120

9718mm

1.222020 20

1.457520

87

⫺50 to ⫺52 ⫺60

⫺41.5

1.1122 1.050

178.5

1.440520

140–142

121

55

7510mm 160

20 20

43, 1864

flammable solid oxidizer

0.906

1.11825 4

Solubility in 100 parts solvent

s most org solvents v sl s aq; misc most org solvents

46

106

dec aq

187.3

85

205

73

INTERACTIVE

b157

Formula

ROTATED

Name

LEFT

No.

b170 b171 b172 b173

b174 b175

b176

1.111

b177

b178

b179

b181 b182

Bis(4-chlorophenyl) sulfone, c223

320.05

53, 1830

110

similar to b168

(ClC6H4)2C(OH)CH3

267.16

63, 3396

69

s org solvents

ClC6H4SO2C6H4Cl

287.16

6, 327

145–148

ClC6H4S(O)C6H4Cl

271.17

61, 149

141–144

(ClC6H4)2CHCCl3

354.49

53, 1833

109–111

[-CH2Si(CH3)Cl2]2

256.11

44, 192

[ClCH(CH3)2Si]2O

300.16

[(C2H5O)2CHCH2]2NCH3

263.38

4, 311

[(C2H5)2NC6H4]2C"O

324.47

14, 98

95

(CH3)2NC6H4]2C"O

268.35

14, 89

172

⬎360 d

[(CH3)2N]Si(CH3)2

146.31

44, 4143

0.81022

1.417020

⫺98

128–129

[(CH3)2NCH2]2CHOH

146.23

4, 290

0.897

1.442220

[C6H5C(CH3)2]2C6H3OH

330.47

64, 5076

[(CH3)2C6H3]2CHCH3

238.38

53, 1908

0.982

[(CH3)2NC("S)S-]2

240.43

4, 76

1.29

Bis(2-cyanoethyl) ether, a62

25010mm

58 acet; 78 bz; 45 chl; v s pyr, 1,4-dioxane

1.263

1.476020

1.221320 4

1.466020

14940mm

0.945

1.425920

222244mm

33–35

210

90

60

s alc, warm bz; v sl s eth; i aq ⫺7 ⬎110

63–65 1.564020

20615mm 1745mm

155–156

⬎110 s alc, eth; sl s bz, acet; i aq

ROTATED

b183

(ClC6H4)2CHCHCl2

RIGHT

b180

2,2-Bis(4-chlorophenyl)-1,1-dichloroethane 1,1-Bis(4⬘-chlorophenyl)ethanol Bis(4-chlorophenyl) sulfone Bis(4-chlorophenyl) sulfoxide 1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethane 1,2-Bis(dichloromethylsilyl)ethane 1,3-Bis(dichloromethyl)tetramethyldisiloxane N,N-Bis(2,2-diethoxyethyl)methylamine 4,4⬘-Bis(diethylamino)benzophenone 4,4⬘-Bis(dimethylamino)benzophenone Bis(dimethylamino)dimethylsilane 1,3-Bis(dimethylamino)-2-propanol 2,4-Bis(␣,␣-dimethylbenzyl)phenol 1,1-Bis(3,4-dimethylphenyl)ethane Bis(dimethylthiocarbamyl) disulfide

DEAN 37261 (McGHP)

b169

INTERACTIVE

No.

Name

b184

Bis(3,4-epoxycyclohexylmethyl) adipate 1,4-Bis(2,3-epoxy-propoxy)butane

b185 b186 b187 b188 b189

1.112

b190

b191 b192

b194

b196 b197 b198

Refractive index

366.46

1.149

1.4930

[H2C 9 CHCH2OCH2CH2⫽]2

202.25

1.049

1.453020

O (C2H5OCH2CH2)2O

162.23

12, 519

0.90720 4

1.411020

370.58

23, 1715

0.990

241.46

43, 388

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C ⬎110

16011mm

⬎110

188

82

1.442520

1671mm

⬎110

0.805

1.442520

1235mm

⬎110

613.28

1.240

1.50020

2330.3mm

⬎110

CH3(CH2)3CH(C2H5)CH2OOC(CH2)8COOCH2CH(C2H5)(CH2)3CH3 [CH3(CH2)3CH(C2H5)CH2O]2P(O)OH [CH3(CH2)3CH(C2H5)CH2O]2POH [CH3(CH2)3CH(C2H5)CH2OOC]2C6H4 [CH3(CH2)3CH(C2H5)CH2OOC]2C6H4 (FC6H4)2CH2

426.66

0.911925 25

1.449625

0.965

1.443020

20910mm

⬎110

0.916

1.442020

0.984320

1.485920

390.56

Merck: 12, 1291 9,4, 3306

0.980

204.22

53, 1789

1.145

[H2N(CH2)6]2NH

215.39

HOCH2CH2OCH2C#CCH2OCH2CH2OH HOCH2CH2OCH2CH2OH

174.20 106.12

1, 468

(HOCH2CH2)2NCH2COOH

163.17

Merck: 12, 1248

[-CH2CH2CO2CH(C2H5)(CH2)3CH3]2 [CH3(CH2)3CH(C2H5)(CH2)3CH3]2

322.43

14, 1786

306.43 390.56

⫺45

⫺60

384

218

1.490020

400

⬎110

1.536220

29–30

260742mm

⬎110

33–36

1654mm

⬎110

1.485020

1.118420 20

1.446020

v s aq, alc, org solvents

⬎110 ⫺50 to ⫺55 30–34

1.144

Solubility in 100 parts solvent

0.01 aq

⬎110 ⫺10.4 193–195

246

118

misc aq, alc, acet, eth 17.9 aq0

INTERACTIVE

b199

Beilstein reference

ROTATED

b195

Bis(2-ethylhexyl) hydrogen phosphate Bis(2-ethylhexyl) hydrogen phosphite Bis(2-ethylhexyl) o-phthalate Bis(2-ethylhexyl) 1,4-phthalate Bis(4-fluorophenyl)methane Bis(hexamethylene)triamine 1,4-Bis(2-hydroxyethoxy)-2-butyne Bis(2-hydroxyethyl) ether N,N-Bis(2-hydroxyethyl)glycine

Formula weight

LEFT

b193

Bis(2-ethoxyethyl) ether Bis(2-ethylhexyl) adipate Bis(2-ethylhexyl)amine Bis(2-ethylhexyl) chlorendate Bis(2-ethylhexyl) decanedioate

Density, g/mL

Formula

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

b201

b202

b203

b204 b205 b206

1.113

b207

b208 b209

2,6-Bis(hydroxymethyl)-p-cresol 2,2-Bis(hydroxymethyl)propanoic acid 4,8-Bis(hydroxymethyl)tricyclo[5.2.1.02,6]decane 4,4-Bis(4-hydroxyphenyl)pentanoic acid

CH3C6H2(CH2OH)2OH

168.19

6, 1127

128–130

(HOCH2)2C(CH3)COOH

134.13

3, 401

181–185

196.29

64, 5538

CH3C(C6H4OH)2CH2CH2COOH

286.33

Merck: 12, 3370

Bis(2-hydroxypropyl) ether 1,3-Bis(isocyanatomethyl)benzene 1,3-Bis(isocyanatomethyl)cyclohexane 1,3-Bis(1-isocyanato1-methylethyl)benzene Bis(2-mercaptoethyl) ether Bis(2-mercaptoethyl) sulfide

HO(CH2)3O(CH2)3OH

134.18

12, 537

1.025220 20

1.441020

C6H4(CH2NCO)2

188.19

133, 334

1.202

1.591020

C6H10(CH2NCO)2

194.24

1.101

1.485020

C6H4[C(CH3)2NCO]2

244.30

1.060

1.511020

(HSCH2CH2)2O

138.25

1.114

(HSCH2CH2)2S

154.32

1.183

1.528020

110

171–172 higher melting form

Bis(2-hydroxyethyl) sulfide, t144 2,2-Bis(hydroxymethyl)-1,3-propanediol, p19

⫺7

231.8

137

1302mm

⬎110

misc aq, alc

⬎110

⫺80 1.596120

s hot aq, acet, alc, HOAc, MeEtKe

1060.9mm

153

217

98

13610mm

90

Bis(4-hydroxyphenyl) sulfide, t145 4,4-Bis(hydroxyphenyl)valeric acid, b203

RIGHT

Bis(2-ethylhexyl) sebacate, b190 1,2-Bis(2-hydroxyethoxy)ethane, t280

s aq, MeOH; sl s acet; i bz

DEAN 37261 (McGHP)

b200

ROTATED

b184

b189

b202

INTERACTIVE

1,4-Bis(methanesulfonoxy)butane 1,2-Bis(methoxyethoxy)ethane Bis[2-(2-methoxyethoxy)ethyl] ether Bis(2-methoxyethyl)amine Bis(2-methoxyethyl) ether 2,2-Bis(4-methoxyphenyl)-1,1,1trichloroethane Bis(2-methylallyl) carbonate Bis(3-nitrophenyl) disulfide Bis(octadecyl)pentaerythritol diphosphite 1,4-Bis(5-phenyloxazol-2-yl)benzene N,N⬘-Bis(salicylidene)1,4-butanediamine N,N⬘-Bis(salicylidene)ethylenediamine N,N⬘-Bis(salicylidene)1,6-hexanediamine Bis(p-tolyl) disulfide Bis(p-tolyl) sulfoxide Bis(tributyltin) oxide 1,4-Bis(trichloromethyl)benzene

b211 b212 b213 b214 b214a

1.114

b215 b216 b217

b218 b219 b220 b221 b222 b223 b224 b225

Formula weight

(CH3SO2OCH2CH2-)2

246.30

(CH3OCH2CH2OCH2-)2

178.23

(CH3OCH2CH2OCH2CH2)2O

228.28

Beilstein reference

Density, g/mL

Refractive index

Flash point,⬚C

Solubility in 100 parts solvent

0.99020 4

1.422420

⫺45

216

110

sl hyd aq; 0.1 alc; 1.4 acet misc aq

13, 2107

1.008720 4

1.433020

⫺27

275

140

s aq

172

58

162

67

133.19

43, 691

0.902

1.419020

(CH3OCH2CH2)2O

134.18

12, 520

0.944025

1.404325

(CH3OC6H4)2CHCCl3

345.66

6, 1007

[H2C"C(CH3)CH2O]2C"O

170.21

O2NC6H4SSC6H4NO2

308.33

[C18H37OP(OCH2)2-]2

721.01

0.943

⫺64 to ⫺68 86–88

1.437020

6, 339 0.925

1.457

misc aq v sl s aq; s alc

202

72

83

364.40

HOC6H4CH"N(CH2)6N"CHC6H4OH CH3C6H4SSC6H4CH3 CH3C6H4S(:O)C6H4CH3 (C4H9)3SnOSn(C4H9)3 Cl3CC6H4CCl3

Boiling point,⬚C

115–117

(CH3OCH2CH2)2NH

HOC6H4CH"N(CH2)4N"CHC6H4OH (-CH2N"CHC6H4OH)2

Melting point,⬚C

i aq; s alc; v s eth

40

261

244

296.37

83, 163

88–90

268.32

8, 48

128

3

324.44

8 , 165

69

246.39 230.33 596.08 312.84

6, 425 6, 419

43–46 94–96 1.170

5, 385

1.486020

i aq; s alc; v s eth v s alc, bz, chl, eth 1802mm

108–110

⬎110 i aq; 26 acet; 38 bz

INTERACTIVE

b210

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

b227 b228 b229 b230

b231 b232

b233

1.115

b234 b235

b236

Bis(2,4,5-trichlorophenyl) disulfide 1,2-Bis(trichlorosilyl)ethane 3,5-Bis(trifluoromethyl)aniline 1,3-Bis(trifluoromethyl)benzene N,O-Bis(trimethylsilyl)acetamide

Cl3C6H2SSC6H2Cl3

425.01

Cl3SiCH2CH2SiCl3

296.94

Bis(trimethylsilyl)acetylene Bis(trimethylsilyl)formamide

(CH3)3SiC#CSi(CH3)3 HC " NSi(CH3)3

N,O-Bis(trimethylsilyl)hydroxylamine 1,2-Bis(trimethylsilyloxy)ethane N,O-Bis(trimethylsilyl)trifluoroacetamide 1,3-Bis(trimethylsilyl)urea

(F3C)2C6H3NH2

229.13

(F3C)2C6H4

214.11

140–144 44, 4266

1.48320 4

1.475020

24.5

20

202 15mm

65

1.467

1.4340

85

83

1.379025

1.391625

116

26

0.83220 4

1.417020

7335mm

11

170.41

0.77020 4

1.427020

137

2

189.41

0.885

1.438120

5513mm

(CH3)3SiONHSi(CH3)3

177.40

0.830

1.411220

80100mm

28

(CH3)3SiOCH2CH2OSi(CH3)3

206.43

0.842

1.403420

166

46

F3C["NSi(CH3)3]OSi(CH3)3

257.40

0.969

1.383920

5014mm

23

(CH3)3SiNHCONHSi(CH3)3

204.42

CH3 9 C " N 9 Si(CH3)3

53, 834

203.43

O9Si(CH3)3

DEAN 37261 (McGHP)

b226

OSi(CH3)3

232 dec

Bis-tris propane, b237

2-Bornanone, c3

RIGHT

1,2-Bis(2-methoxyethoxy)ethane, t282 Bis(phenylmethyl) disulfide, d72

⫺10

ROTATED

b218

INTERACTIVE

Beilstein reference

Density, g/mL

CH2[CH2NHC(CH2OH)3]2

282.34

43, 859

H2NC("O)NHC("O)NH2 (CH3)3CNH2 ·BH3 C6H5N(C2H5)2 ·BH3

103.08 86.97 163.07

3, 70

[(CH3)2CH]2C2H5 ·BH3

143.08

0.822

58.92 75.97

0.801

b244 b245 b246 b247 b248 b249 b250 b251 b253

1,3-Bis[tris(hydroxymethyl)methylamino]propane Biuret Borane-tert-butylamine Borane-N,N-diethylaniline Borane-N,N-diisopropylethylamine Borane-dimethylamine Borane-dimethyl sulfide Borane-pyridine (1S-endo)-(⫺)-Borneol (⫺)-1-Bornyl acetate N-Bromoacetamide p-Bromoacetanilide Bromoacetic acid Bromoacetonitrile 2-Bromoacetophenone p-Bromoacetophenone

b254 b255 b256 b257 b258 b259 b260 b261 b262

Bromoacetyl bromide Bromoacetyl chloride 2-Bromoaniline 3-Bromoaniline 4-Bromoaniline 2-Bromoanisole 4-Bromoanisole 3-Bromobenzaldehyde Bromobenzene

b241 b242 b243

(CH3)2NH·BH3 (CH3)2S·BH3

1.116

C5H4N·BH3

CH3CON(Br)H BrC6H4NHCOCH3 BrCH2COOH BrCH2CN C6H5COCH2Br BrC6H4COCH3

92.93 154.25 196.29 137.96 214.06 138.95 119.95 199.05 199.05

6, 72 6, 82 2, 181 12, 642 2, 213 2, 216 7, 283 7, 283

BrCH2COBr BrCH2COCl BrC6H4NH2 BrC6H4NH2 BrC6H4NH2 BrC6H4OCH3 BrC6H4OCH3 BrC6H4CHO C6H5Br

201.86 157.40 172.03 172.03 172.03 187.04 187.04 185.03 157.01

2, 215 2, 215 12, 631 12, 633 12, 636 6, 197 6, 199 7, 238 5, 206

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

170

1.4674⫺5

0.920 1.01120 4 0.982 1.717 1.93450 4 1.722 1.64720 4 1.647 2.31722 22 1.908 1.57820 4 1.58020 4 1.4970100 4 1.502 1.494 1.587 1.495220 4

anhyd 110 100 dec ⫺30 1.460020

1.532020 1.4626

1.480450 1.480020

1.574020 1.564020 1.593520 1.560220

v s alc; 2 aq25

dec 190 21 40

36

43 18

50 54 1.548020 1.496020 1.622320 1.625020

s aq

15–17

10–11 204 27 102–105 168 50

31 16.8 66.3 2 9–10 ⫺30.6

Solubility in 100 parts solvent

210779mm 224

21 65 84

208 6224mm 13518mm 255

⬎110 ⬎110 ⬎110 ⬎110

150 128 229 251

none none ⬎110 ⬎110

223 223 230 156

96 94 96 51

i aq; 176 alc; s eth v sl s aq; s alc, eth sl s aq; v s eth s alc, bz, chl, EtOAc v s aq, alc v s alc, bz, chl, eth s alc, bz, CS2, HOAc PE dec aq, alc dec aq, alc i aq; s alc, eth sl s aq; s alc, eth i aq; v s alc, eth

INTERACTIVE

i aq; v s alc, eth 0.045 aq30; 10.4 alc25; 71.6 eth25; misc bz, chl, PE

ROTATED

b237

Refractive index

LEFT

Name

b238 b239 b240

Formula

Formula weight

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

b265 b266 b267 b268 b269 b270 b271 b272

1.117

b273 b274 b275 b276 b277 b278 b279 b280

Bromobenzene-d5 4-Bromobenzenesulfonyl chloride 2-Bromobenzoic acid 4-Bromobenzoic acid 4-Bromobenzophenone 2-Bromobenzotrifluoride 3-Bromobenzotrifluoride 3-Bromobenzoyl chloride 4-Bromobenzyl bromide ␣-Bromobenzyl cyanide 4-Bromobiphenyl 1-Bromobutane 2-Bromobutane 1-Bromo-2-butene 2-Bromo-2-butene 4-Bromo-1-butene 4-Bromobutyl acetate 1-Bromo-4-tert-butylbenzene

1.558520

5323mm 15315mm

51

82

350

1.482020

168

51

1.613

1.473020

152

43

1.662

1.596520

750.5mm

107

C6D5Br BrC6H4SO2Cl

162.06 255.52

11, 57

BrC6H4COOH BrC6H4COOH BrC6H4COC6H5

201.02 201.02 261.12

9, 347 9, 351 7, 422

BrC6H4CF3

225.01

1.65220

BrC6H4CF3

225.01

BrC6H4COCl

219.47

9, 350

BrC6H4CH2Br

249.94

5, 308

C6H5CH(Br)CN

196.05

BrC6H4C6H5 CH3CH2CH2CH2Br CH3CH2CHBrCH3 CH3CH"CHCH2Br CH3CH"C(Br)CH3 BrCH2CH2CH"CH2 CH3CO2(CH2)4Br (CH3)3CC6H4Br

233.11 137.02 137.02 135.01 135.01 135.01 195.06 213.12

5, 580 1, 119 1, 119 1, 205 1, 205 11, 84 23, 39 5, 416

74.5

i aq; s alc (dec); v s eth

148–150 251–253

1.92925 4

1.619320

61

12412mm

⬎110

1.53929 4

1.569620

29

242 dec

⬎110

0.932725 4 1.268625 4 1.258520 1.312 1.328 1.323020 4 1.348 1.229

1.437425 1.436020 1.476520 1.459020 1.460820 1.460020 1.533020

90–92 ⫺112.4 ⫺112.7

310 101.6 91.4 99 90740mm 100 9312mm 812mm

18 21 11 1 9 109 97

p-Bromobenzenethiol, b428 4-Bromobenzyl cyanide, b397

15–16

0.18 aq25; s alc, eth i alc; sl s bz, eth

s aq, alc, bz, eth, CS2, HOAc sl s aq; v s alc, acet, eth. A war gas. i aq; s alc, bz, eth i aq; s alc, bz, eth ⬍0.1 aq; v s alc, eth Mixture of cis, trans i aq; s alc, eth

exo-2-Bromobicyclo[2.2.1]heptane, b383 Bromobutanedioic acid, b421

RIGHT

Bromal, t199 Bromoacetaldehyde diethyl acetal, b317 Bromoanisoles, b357, b358, b359

1.539

DEAN 37261 (McGHP)

b263 b264

ROTATED

b245

b246

INTERACTIVE

4-Bromobutyl phenyl ether 2-Bromobutyric acid ␣-Bromo-␥-butyrolactone [1R-endo]-(⫹)-3Bromocamphor 1-Bromocarbonyl-1methylethyl acetate 2-Bromo-4⬘-chloroacetophenone 2-Bromochloro-benzene 3-Bromochloro-benzene 4-Bromochlorobenzene 3-Bromo-4-chlorobenzotrifluoride 1-Bromo-4-chlorobutane 4⬘-Bromo-4-chlorobutyrophenone 4-Bromo-6-chloro-ocresol Bromochlorodifluoromethane 3-Bromo-1-chloro-5,5dimethyl-hydantoin 1-Bromo-2-chloroethane Bromochlorofluoromethane

b282 b283 b284 b285 b286 b287

1.118

b288 b296 b297 b298 b299 b300 b301 b302 b303 b303a

Formula weight

Beilstein reference

Density, g/mL

C6H5O(CH2)4Br

229.12

62, 82

CH3CH2CH(Br)COOH

167.00 164.99

2, 281

1.566920 20 1.99020

231.14

7, 120

1.449

Refractive index

1.472020 1.508020

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

41–43

15618mm

⬎110

⫺4

10310mm 1386mm

⬎110 ⬎110

75–78

244

Solubility in 100 parts solvent

6.7 aq; s alc, eth

15 alc; 200 chl; 62 eth; s olive oil

1.431

1.457020

7712mm

110

5, 209

1.638225 4

1.578925

204

79

i aq; v s bz

191.46

5, 209

1.630220 4

1.577020

⫺21

196

80

i aq; v s alc, bz, eth

BrC6H4Cl

191.46

5, 209

1.57671 4

1.553170

66

196

Br(Cl)C6H3CF3

259.46

53, 715

1.726

1.499020

⫺22

190

94

ClCH2CH2CH2CH2Br

171.47

53, 294

1.488

1.487520

8230mm

60

BrC6H4CO(CH2)3Cl

261.55

Br(Cl)C6H2(OH)CH3

221.49

CH3CO2C(CH3)2COBr

209.05

ClC6H4COCH2Br

233.50

BrC6H4Cl

191.46

BrC6H4Cl

Br(Cl)CF2

6, 360

165.36 241.48

ClCH2CH2Br

143.41

Br(Cl)CHF

149.37

36–38

⬎110

45–47

⬎110

⫺160

6.579 g/L

0.1 aq; misc MeOH, eth

i aq; s alc, chl, eth

⫺3.7

160–164 1, 89

1.739220 4

1.491720

⫺18.4

106.6

1.97710

1.414455

⫺115

36

0.7 aq; misc org solv

INTERACTIVE

b281

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

b305 b306 b307 b308 b309 b310 b311

1.119

b312 b313 b314 b315 b316 b317 b318 b319

7-Bromo-5-chloro-8hydroxyquinoline Bromochloromethane 1-Bromo-3-chloro-2methylpropane 1-Bromo-3-chloropropane 2-Bromo-2-chloro1,1,1-trifluoroethane 2-Bromocinnamaldehyde Bromocycloheptane Bromocyclohexane 3-Bromocyclohexene Bromocyclopentane Bromocyclopropane 1-Bromodecane Bromodichloromethane 2-Bromo-1,1-diethoxyethane 4-Bromo-1,2-dimethoxybenzene 2-Bromo-1,1-dimethoxyethane

ClCH2Br

258.51

211, 222

129.38

1, 67

177–179 1.92325 4

3

1.48025

⫺88

20

ClCH2CH(CH3)CH2Br

171.47

1 , 324

1.467

1.4809

ClCH2CH2CH2Br

157.44

1, 109

1.492

1.485120

BrCH(Cl)CF3

197.39

14 156

1.863625

1.369120

C6H4CH"C(Br)CHO

211.06

7, 358

Br(C7H13) Br(C6H11)

177.09 163.06

5, 29 5, 24

1.288722 4 1.326415 4

Br(C5H9) Br(C3H5) CH3(CH2)9Br BrCHCl2

161.04 149.04 120.98 221.18 163.83

52, 40 5, 19

BrCH2CH(OC2H5)2

68

0.9 aq; misc MeOH, eth

154 ⬍⫺50

⬎110

143.5

0.1 aq; misc org solv

50.2

none

1.505220 1.495615

7210mm 165.8

68 62

12, 130 1, 67

1.389020 4 1.390020 4 1.510 1.065820 4 1.98020

1.529220 1.488120 1.460529 1.456020 1.496720

6515mm 137–139 69 238–240 87

54 35 ⫺6 94 none

i aq; v s chl, eth sl s aq; misc org solv

197.08

1, 625

1.310

1.438520

6718mm

51

s hot alc

BrC6H3(OCH3)2

217.07

6, 784

1.702

1.574320

BrCH2CH(OCH3)2

169.02

1, 624

1.430

1.445020

66–68

⫺30 ⫺55

256

i aq; v s chl, eth 0.1 aq; 10 MeOH; 71 eth

109 150

53

RIGHT

␤-Bromocumene, b350

2-Bromo-p-cumene, b351

DEAN 37261 (McGHP)

b304

ROTATED

b283

b284

b302

b304

b312

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

b320

1-Bromo-2,2-dimethoxypropane 4-Bromo-2,6-dimethylphenol 3-Bromo-2,2-dimethyl1-propanol 2-Bromo-4,6-dinitroaniline 1-Bromo-2,4-dinitrobenzene 4-Bromodiphenyl ether 1-Bromodiphenylmethane 1-Bromododecane 1-Bromo-2,3-epoxypropane

b321 b322 b323 b324 b325 b326

1.120

b327 b328

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

1.355

1.447520

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

8780mm

40

184–187

75

CH3C(OCH3)2CH2Br

185.05

BrC6H2(CH3)2OH

201.07

6, 485

BrCH2C(CH3)2CH2OH

167.05

11, 201

BrC6H2(NO2)2NH2

262.03

12, 761

BrC6H3(NO2)2

247.01

BrC6H4OC6H5 C6H5CH(Br)C6H5

249.11 247.14

61, 105 5, 592

1.423

1.607020

18 40–42

305 18420mm

⬎110 ⬎110

CH3(CH2)11Br H2C 9 CHCH2Br

249.24 136.98

12, 133 17, 9

1.038 1.60120

1.458020 1.482020

⫺11 ⫺40

1356mm 134–136

⬎110 56

0.1 aq; s alc, eth i aq; sl s alc; s eth

O CH3CH2Br

108.97

1, 88

1.461220 4

1.424220

⫺119

38.2

⫺23

0.91 aq20; misc alc, chl, eth

5720mm

⬎110

159

71

misc aq; s org solv except PE v s aq; misc alc, eth v s aq, alc

79–81 1.358

1.479420 154

subl

v s hot alc, hot acet

71–73

2-Bromoethanesulfonic acid, sodium salt 2-Bromoethanol

BrCH2CH2SO2⫺ Na⫹

211.02

4, 7

BrCH2CH2OH

124.98

1, 338

1.762920 4

1.493620

2-Bromoethyl acetate 2-Bromoethylamine HBr (1-Bromoethyl)benzene (2-Bromoethyl)benzene 1-Bromo-2-ethylbenzene Bromoethylene

CH3CO2CH2CH2Br BrCH2CH2NH2 ·HBr

167.01 204.90

21, 57 4, 134

1.51420 4

1.454720

C6H5CH(CH3)Br

185.07

5, 355

1.356

1.560020

9416mm

81

C6H5CH2CH2Br

185.07

5, 355

1.355

1.556020

221

89

BrC6H4CH2CH3

185.07

5, 355

1.338

1.549020

19416mm

71

H2C"CHBr

106.95

1, 188

1.49320

1.438020

15.8

none

b332 b333 b334 b334a b335 b336

283 dec

⫺13.8 172–174

⫺139

i aq; misc alc, eth

INTERACTIVE

b330

ROTATED

Bromoethane

LEFT

b329

b331

Solubility in 100 parts solvent

b338 b339 b340 b341 b342 b343 b344 b345 b346 b347

1.121

b348 b350 b351 b352

4-Bromodiphenyl ether, b295 Bromoethene, b336

1.357220 4

1.445020

BrCH2CH2OCH2CH3

153.02

1, 338

BrCH2CH2OC6H5

201.07

6, 142

34

254.09

21, 461

81–84

150

21

sl s aq; misc alc, eth

14440mm

65

i sq; v s alc, eth s hot aq; v s eth

BrC6H4F

175.01

1.601

1.533720

156

43

BrC6H4F

175.01

1.567

1.525720

150

38

BrC6H4F

175.01

5, 209

1.59315

1.531015

⫺17.4

152

60

H(CH2)7Br H(CH2)5CH(Br)CH3 H(CH2)16Br H(CH2)6Br CH3(CH2)3CH(Br)COOH

179.11 179.11 305.35 165.08 195.06

1, 155 1, 155 12, 138 1, 144 2, 325

1.138420 4 1.142 0.9991 1.176320 4 1.370

1.450520 1.447020 1.461820 1.447520 1.472020

⫺58

180 6621mm 336 154–158 13818mm

60 47 177 57 ⬎110

C6H5CH(CH3)CH2Br

226.03 199.10

21, 453 51, 191

1.316

1.548020

10818mm

91

CH3(Br)C6H3CH(CH3)2

213.0

1.25325 25

1.53525

1,3,5-(CH3)3C6H2Br CH3Br BrC6H4CH(OH)COOH

17.8 ⫺85

i aq; v s alc, eth i aq; misc org solv i aq; misc alc, eth s alc, eth

251–253

176.96

17, 435

1.905

1.540020

199.10 94.94 231.05

5, 408 1, 67 10, 210

1.301 1.73200

1.552020 1.423410

Bromoform, t204

⫺20

2 ⫺94 117–118

120

i aq; 50 MeOH; misc org solvents

215

⬎110

255 3.56

96 none

2-Bromomesitylene, b436

0.1 aq; s alc, chl, eth sl s aq

RIGHT

b353 b354 b355

2-Bromoethyl ethyl ether 2-Bromoethyl phenyl ether N-(2-Bromoethyl)phthalimide 1-Bromo-2-fluorobenzene 1-Bromo-3-fluorobenzene 1-Bromo-4-fluorobenzene 1-Bromoheptane 2-Bromoheptane 1-Bromohexadecane 1-Bromohexane DL-2-Bromohexanoic acid 5-Bromoisatin (2-Bromoisopropyl)benzene 2-Bromo-4-isopropyl1-methylbenzene Bromomaleic anhydride 2-Bromomesitylene Bromomethane 4-Bromomandelic acid

DEAN 37261 (McGHP)

b337

ROTATED

b339

b348

INTERACTIVE

b352

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

5-Bromo-2-methoxybenzaldehyde 2-Bromo-1-methoxybenzene 3-Bromo-1-methoxybenzene 4-Bromo-1-methoxybenzene 4-Bromo-2-methylaniline 1-Bromo-3-methylbenzyl alcohol 1-Bromo-3-methylbutane 2-Bromo-2-methylbutane 2-Bromo-3-methylbutanoic acid 4-Bromo-2-methyl-2butene (Bromomethyl)chlorodimethylsilane (Bromomethyl)cyclohexane 2-Bromomethyl-1,3dioxalane Bromomethyl methyl ether 1-Bromo-2-methylnaphthalene 1-Bromo-2-methylpropane

b357 b358 b359 b360 b361

1.122

b362 b363 b364 b365 b366 b367 b368 b369 b370 b371

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

BrC6H3(OCH3)CHO

215.05

8, 55

116–119

BrC6H4OCH3

187.04

6, 197

1.501820 4

1.573720

2

223

BrC6H4OCH3

187.04

6, 198

1.477

1.563520

211

93

BrC6H4OCH3

187.04

6, 199

1.456420 4

1.563020

10

223

94

sl s aq; v s alc, eth

CH3(Br)C6H3NH2

186.06

12, 838

57–59

240

⬎110

sl s aq; v s alc

BrC6H4CH(CH3)OH

201.07

62, 447

1.460

36–38

1217mm

63

(CH3)2CHCH2CH2Br

151.05

1, 136

1.21015 4

1.440920

⫺112

119.7

32

C2H5C(CH3)2Br

151.05

1, 136

1.182

1.442320

107735mm

5

(CH3)2CHCH(Br)COOH

181.04

2, 317

12620mm

107

BrCH2C"C(CH3)2

149.04

12, 189

1.293

1.489820

6060mm

32

BrCH2Si(CH3)2Cl

187.5

44, 4024

1.375

1.465020

130740mm

41

(C6H11)CH2Br

177.09

52, 18

1.269

1.490720

7726mm

57

167.01

192, 8

1.613

1.481720

8227mm

62

BrCH2OCH3

124.97

1, 582

1.531

1.455020

87

26

Br(C10H6)CH3

221.10

5, 568

1.418

1.648620

296

⬎110

(CH3)2CHCH2Br

137.03

1, 126

1.264120

1.436220

91.5

18

44

⫺119

96

i aq; v s alc, eth i aq; s alc, eth

0.02 aq; misc alc, eth

sl s aq; s alc, eth

0.06 aq; misc alc, eth

INTERACTIVE

b356

Formula

ROTATED

Name

LEFT

No.

b373 b374 b375 b376 b377 b378 b379 b380 b381

1.123

b382 b383 b384 b385 b386

(Bromomethyl)benzene, b85 4-Bromo-1-methylbenzene, b431

(CH3)3CBr

137.03

1, 127

1.212525 4

BrC(CH3)2COOH

167.01

2, 295

1.52

1.42525

⫺16.2

73.1

18

i aq; misc org solv

48–49

200

⬎110

sl s aq; s alc, eth; dec by hot aq

24

(CH3)2C(Br)COBr

229.91

2, 297

1.860

1.5064

164

110

C6H5CO(CH3)2Br

227.11

7, 316

1.350

1.556120

14830mm

⬎112

(C10H7)Br BrC10H6OH BrC10H6OH BrC6H4NO2

207.07 233.07 223.07 202.01

5, 547 6, 650 6, 650 51, 247

1.483420 4

1.658020

1.624580 4

O2N(Br)C6H3CF3

270.02

53, 755

1.799225

(HOCH2)2C(Br)NO2

199.99

1, 476

H(CH2)9Br

207.16 175.07

11, 63

1.084 1.363

1.454020 1.514820

H(CH2)18Br H(CH2)8Br BrC6F5

333.41 193.13 246.97

11, 69 1, 160

0.976 1.10825 4 1.94720

1.451825 1.449020

H(CH2)5Br CH3CH2CH2CH(Br)CH3 C2H5CH(Br)C2H5 CH3CO2(CH2)5Br

151.05 151.05 151.05 209.09

1, 131 1, 131 11, 43 23, 249

1.223715 4 1.203920 4 1.216 1.255

1.444420 1.440320 1.444520 1.462020

1.518025

⫺1.8 78 78–81 43

281 130 dec

⬎110

misc alc, bz, chl, eth i aq; s alc, bz, eth

261

110

v s alc; s bz, eth

33–35

1005mm

⬎110

120–122

2-Bromo-2-methylpropanoyl bromide, b374

s aq, alc, EtOAc; sl s bz, acet, chl, eth i aq; s chl, eth

201 8229mm

90 60

23 ⫺55 ⫺31

21612mm 201 137

⬎110 78 87

i aq; s alc, eth i aq; misc alc, eth

⫺88

129.6 117 119 11015mm

31 20 18 ⬎110

i aq; s alc; misc eth

␣-Bromo-p-nitrotoluene, n44

RIGHT

b387 b388 b389 b390

2-Bromo-2-methylpropane 2-Bromo-2-methylpropanoic acid 2-Bromo-2-methylpropionyl bromide 2-Bromo-2-methylpropiophenone 1-Bromonaphthalene 1-Bromo-1-naphthol 1-Bromo-2-naphthol 1-Bromo-2-nitrobenzene 5-Bromo-2-nitrobenzotrifluoride 2-Bromo-2-nitro-1,3propanediol 1-Bromononane exo-2-Bromo-norbornane 1-Bromooctadecane 1-Bromooctane Bromopentafluorobenzene 1-Bromopentane 2-Bromopentane 3-Bromopentane 5-Bromopentyl acetate

DEAN 37261 (McGHP)

b372

ROTATED

b368

b383

INTERACTIVE

b391 b392 b393 b394 b395

b400 b401

9-Bromophenanthrene 2-Bromophenol 3-Bromophenol 4-Bromophenol 1-(4-Bromophenoxy)1-ethoxyethane 4-Bromophenylacetic acid 4-Bromophenylacetonitrile 4-Bromophenyl phenyl ether 1-Bromo-3-phenylpropane 1-Bromopropane 2-Bromopropane

b402 b403 b404 b405 b406 b407 b408 b409

b396 b397 b398

1.124

b399

b410 b411

Formula weight

Beilstein reference

Density, g/mL

Refractive index

1.409101 4 1.492

1.589220

1.587580 1.348

1.522920

Melting point,⬚C

BrC6H4OH BrC6H4OH BrC6H4OH CH3CH(OC6H4Br)OC2H5

257.14 173.01 173.01 173.01 245.12

5, 671 6, 197 6, 198 6, 198

54–58 6 32 64

BrC6H4CH2COOH

215.05

9, 451

119

BrC6H4CH2CN

196.05

9, 451

47–49

BrC6H4OC6H5

249.11

61, 105

1.423

1.607020

BrC6H4CH2CH2CH2Br

199.10

5, 391

1.310

1.545020

CH3CH2CH2Br CH3CH(Br)CH3

122.99 123.99

1, 108 1, 108

1.359715 1.322215

1.437015 1.428515

3-Bromo-1-propanol 1-Bromo-2-propanone

BrCH2CH2CH2OH CH3OCH2Br

139.00 136.98

1.537420 4 1.63423

1.485820 1.469715

1-Bromo-1-propene 2-Bromo-2-propene 2-Bromopropionic acid 3-Bromopropionic acid 3-Bromopropionitrile 2-Bromopropionyl bromide 2-Bromopropionyl chloride 3-Bromopropionyl chloride 2-Bromopropiophenone

CH3CH"CHBr CH3C(Br)"CH2 CH3CH(Br)COOH BrCH2CH2COOH BrCH2CH2CN CH3CH(Br)COBr

120.98 120.98 152.98 152.98 133.98 215.88

1, 356 Merck: 12, 1422 1, 200 1, 200 2, 254 2, 256 22, 231 2, 256

1.413320 4 1.36220 4 1.700020 1.480 1.615220 4 2.061

1.453820 1.442520 1.475020 1.480020 1.518220

CH3CH(Br)COCl

171.43

2, 256

1.70011

CH3CH(Br)COCl

171.43

22, 231

C6H5COCH(Br)CH3

213.08

7, 302

Boiling point,⬚C 1902mm 194 236 238 1258mm

Flash point,⬚C ⬎110 42 ⬎110

14 aq; v s alc, chl

sl s aq; v s alc, eth ⬎110 ⬎110

220

101

⫺110.1 ⫺89.0

71.0 59.5

19

625mm 137

93

⫺36.5

70 47–49 203 7810mm 5010mm

⫺6 4 100 65 98 ⬎110

1.480020

133

51

1.701

1.496820

5717mm

79

1.43020 4

1.571520

250

⬎110

⫺116 ⫺125 25.7 62.5

i aq; s alc, eth s aq; misc chl, eth

106

305

18

Solubility in 100 parts solvent

i aq; sl s alc; v s bz

0.23 aq30; misc alc 0.3 aq18; misc alc, bz, chl, eth s aq; misc alc, eth v sl s aq; s alc, acet i aq v s aq, alc, bz, chl, eth s aq, alc, bz, chl, eth v s alc, eth

d aq; s chl, eth

s alc, bz, eth, acet

INTERACTIVE

b412

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

b414 b415 b416 b417 b418 b419

3-Bromopropyl phenyl ether 3-Bromopropyltrichlorosilane 3-Bromopropyne 2-Bromopyridine 3-Bromopyridine 3-Bromoquinoline 5-Bromosalicylic acid

C6H5OCH2CH2CH2Br

215.10

Br(CH2)3SiCl3

256.44

1.365

1.546420

1.605

1.490020

1.335 1.65718 1.64504 1.533

1.4905 1.572020 1.569520 1.664020

Br(HO)C6H3COOH

1, 248 20, 233 20, 233 20, 363 10, 107

C6H5CH"CHBr HOOCH2CH(Br)COOH

183.05 196.99

5, 477 2, 621

1.42220 4 2.073

1.606620

b422

␤-Bromostyrene (⫾)-Bromosuccinic acid N-Bromosuccinimide

177.99

21, 380

2.098

b423

1-Bromotetradecane

H(CH2)14Br

277.30

12, 136

1.012425 4

1.460020

b424

3-Bromotetrahydro-2methyl-2H-pyran 3-Bromothioanisole 2-Bromothiophene 3-Bromothiophene 4-Bromothiophenol 2-Bromotoluene

179.06

173, 75

1.366

1.483020

203.11 163.04 163.04 189.08 171.04

6, 330 17, 33

1.68420 4 1.740

1.586020 1.591020

1.42225 25

1.55225

1.125

b425 b426 b427 b428 b429

BrC6H4SCH3 Br(C5H3S) Br(C5H3S) BrC6H4SH BrC6H4CH3

142–143 15 166 7 161

13414mm

96

202–204

76

88–90 194 173 276

18 54 51 ⬎110

11220mm

79

173 sl dec 6

17820mm

⬎110

6117mm

57

38–40

(3-Bromopropyl)benzene, b338 3-Bromopropylene, a79

151 150 239 181

76 ⫺26

⬎110 60 56 78

5-Bromopseudocumene, b435 ␣-Bromotoluene, b85

i aq; s org solv s aq; v s alc, eth s HOAc 0.3 aq80; 85 alc25; 70 eth25 i aq; misc alc, eth 18 aq; s alc, acet, eth 1.5 aq25; 14.4 acet25; 3.1 HOAc25 s alc; v s chl; misc bz, acet

v s acet, eth

0.1 aq; misc alc, bz, chl, eth

RIGHT

␤-Bromophenitole, b338 3-Bromopropene, a79

6, 330 5, 304

10–11

20

118.97 158.00 158.00 208.06 217.02

b420 b421

BrCH2C#CH Br(C5H4N) Br(C5H4N)

6, 142

DEAN 37261 (McGHP)

b413

ROTATED

b391

b418

b422

b424

INTERACTIVE

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

BrC6H4CH3 BrC6H4CH3 BrCCl3

171.04 171.04 198.28

5, 305 5, 305 1, 67

1.409920 1.395935 35 1.99725 25

1.551720 1.5490 1.506320

⫺39.8 28.5 ⫺6

183.7 184.5 104–105

60 85

s alc, bz, eth s alc, bz, eth misc org solv

H(CH2)13Br BrCF3

263.27 148.91

12, 134 13, 83

1.026220 4 6.087 g/L

1.459220

15010mm ⫺57.8

⬎110

v s chl v s chl

BrC6H2(CH3)3

199.10

5, 403

7 ⫺168 to ⫺172 73

BrC6H2(CH3)3

199.10

5, 408

(CH3)3GeBr

197.60

(CH3)3SiBr (C6H5)2C"C(Br)C6H5

153.10 335.22

5, 722

115–117

(C6H5)3CBr

323.24

5, 704

152–154

23015mm

CH3(CH2)10Br Br(CH2)10COOH

235.22 265.20

12, 132 22, 315

1.954

⫺9 51

13818mm 1742mm

⬎110 ⬎110

b443 b444 b445 b446 b447

3-Bromotoluene 4-Bromotoluene Bromotrichloromethane 1-Bromotridecane Bromotrifluoromethane 5-Bromo-1,2,4-trimethylbenzene 2-Bromo-1,3,5-trimethylbenzene Bromotrimethylgermane Bromotrimethylsilane Bromotriphenylethylene Bromotriphenylmethane 1-Bromoundecane 11-Bromoundecanoic acid ␣-Bromo-1,2-xylene ␣-Bromo-1,3-xylene 2-Bromo-1,4-xylene 4-Bromo-1,2-xylene Brucine

BrCH2C6H3CH3 BrCH2C6H3CH3 BrCH2C6H3CH3 BrCH2C6H3CH3

185.07 185.07 185.07 185.07 394.45

5, 365 5, 374 5, 385 5, 365 272, 797

1.38123 1.37023 1.340 1.37015 15

21

224 185340mm 199–201 215

82 82 79 80

b448 b449

1,2-Butadiene 1,3-Butadiene

CH3CH"C"CH2 H2C"CHCH"CH2

1, 249 1, 249

0.67610 2.211 g/L

1.42051 1.4293⫺25

10.9 ⫺4.4

⫺76

b450 b451 b452

Butadiene sulfone 1,3-Butadienyl acetate 1,3-Butadiyne

CH3CO2CH"CHCH"CH2 HC#CC#CH

0.945 0.736404

1.469020 1.41895

b430 b431 b432 b433 b434 b435 b436 b437

1.126

b438 b439 b440

173, 144 23, 295 13, 1056

1.551120

2

225

96

1.54418

1.470520

⫺25

113.7

37

1.160

1.414020

79

32

1.456320

1.38120 1.556020 1.550520 1.556020

9–10 178 ⫺136.2 ⫺108.9 66 ⫺36

6040mm 10.3

i aq; s bz; v s eth

i aq; v s alc s alc, eth s alc, eth v s chl, hot ether v s alc, eth 77 alc; 1 bz; 20 chl; 4 EtOAc misc alc, eth misc alc, eth

⬎110 33 v s eth; s acet, bz

INTERACTIVE

118.15 112.13 50.06

1.301

ROTATED

54.09 54.09

i aq; s alc

LEFT

b441 b442

235

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

2-Butanamine Butane

CH3CH2CH(NH2)CH3 CH3CH2CH2CH3

73.14 58.12

4, 160 1, 118

0.730815 4 0.60110

1.396315 1.3562⫺13

⫺104.5 ⫺138.3

66 ⫺0.50

⫺19 ⫺60

b455 b456

1,4-Butanediamine Butanedinitrile

H2NCH2CH2CH2CH2NH2 NCCH2CH2CN

88.15 80.09

4, 264 2, 615

0.87725 4 0.986760 4

1.456920 1.417360

28 54.5

158–160 266

51 132

b457 b457a b457b

1,2-Butanediol 1,3-Butanediol 1,4-Butanediol

CH3CH2CH(OH)CH2OH CH3CH(OH)CH2CH2OH HOCH2CH2CH2CH2OH

90.12 90.12 90.12

1, 477 1, 477 1, 478

1.00618 0 1.005320 20 1.01625 4

1.438020 1.44120 1.445220

⬍⫺50 20

207.5 207.5 235

93 121 121

b458 b459

meso-2,3-Butanediol 1,4-Butanediol dimethanesulfonate 1,3-Butanediol diacetate 1,4-Butanediol diacrylate

CH3CH(OH)CH(OH)CH3 CH3SO2O(CH2)4OSO2CH3

90.12 246.30

1, 479 44, 19

0.993925 4

1.432435

182

85

CH3CO2CH2CH2CH(CH3)O2CCH3 (H2C"CHCO2CH2CH2-)2

174.20

2, 143

1.028

1.419920

998mm

85

198.22

24, 170

1.051

1.456020

830.3mm

⬎110

b460

1.127

b461

BTMSA, b231 Busulfan, b210 1,3-Butadiene diepoxide, d546 Butanal, b612 1-Butanamine, b509

Butanecarbaldehyde, p28 Butanedinitrile, s18 Butanedioic acid, s15 Butanedioic anhydride, s16 1,4-Butanediol diglycidyl ether, b185

b447

O

ROTATED

S O

RIGHT

Bromo-␣,␣,␣-trifluorotoluene, b268, b269 3-Bromo-1,7,7-trimethylbicyclo[2.2.1]heptane-2-one, b284 4-Bromoveratrole, b318 4-Bromo-2,6-xylenol, b321 BSA, b230 BSTFA, b235

25 114–117

misc aq, alc 1 vol aq dissolves 0.15 vol and 1 vol alc 18 vols at 17⬚ and 770 mm; 1 vol ether or CHCl3 dissolves 25 or 30 vols, resp. s aq 11.5 aq; s acet, chl, 1,4-dioxane; sl s bz s aq, alc, acet s aq, alc, acet; 9 eth misc aq, alc, acet; 0.3 bz; 3.1 eth; 0.9 PE misc aq, alc 2.4 acet25; 0.1 alc25

DEAN 37261 (McGHP)

b453 b454

b450

INTERACTIVE

b482 b483 b484

1,3-Butanediol dimethacrylate 1,4-Butanediol dimethacrylate 1,4-Butanediol divinyl ether 1,4-Butanediol vinyl ether 2,3-Butanedione 2,3-Butanedione monoxide 1,4-Butanedithiol Butanenitrile 1,2,3,4-Butanetetracarboxylic acid 1-Butanethiol 2-Butanethiol 1,2,4-Butanetriol 1-Butanol 2-Butanol 2-Butanone 2-Butanone oxime 1-Butene cis-2-Butene trans-2-Butene cis-2-Butene-1,4-diol trans-2-Butene-1,4diol 3-Butenenitrile cis-2-Butenoic acid trans-2-Butenoic acid

H2C"CHCH2CN CH3CH"CHCOOH CH3CH"CHCOOH

b485 b486

3-Butenoic acid cis-2-Buten-1-ol

H2C"CHCH2COOH CH3CH"CHCH2OH

b464 b465 b466 b467

1.128

b468 b468a b469 b470 b471 b472 b473 b474 b475 b476 b477 b478 b479 b480 b481

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

1.010

1.452020

290

⬎110

1344mm

⬎110

6410mm

62

9520

85

86 186

7

25 aq; misc alc, eth

10630mm 117.6

70 24

i aq; v s alc 3.3 aq; misc alc, eth

2 21 167 37 24 ⫺9 60 ⫺80 ⫺73 ⫺73 128

0.06 aq; v s alc, eth sl s aq; v s alc, eth v s aq, alc 7.4 aq; misc alc, eth 12.5 aq; misc alc, eth 24 aq; misc alc, bz, eth

sl s aq; misc alc, eth v s aq; s alc 55 aq; 52 EtOH; 53 acet; 37 toluene s aq; misc alc, eth 16.6 aq; misc alc

H2C"C(CH3)CO2CH2CH2CH(CH3)O2CC(CH3)"CH2 [H2C"C(CH3)CO2CH2CH2-]2

226.28 226.28

24, 1534

1.010

1.456020

(-CH2CH2OCH"CH2)2

142.20

14, 2518

0.898

1.44420

H2C"CHO(CH2)4OH

116.16

14, 2518

0.939

1.444020

CH3C("O)C("O)CH3 CH3C("NOH)C("O)CH3

86.09 101.11

1, 769 1, 772

0.99015 15

1.395120

HSCH2CH2CH2CH2SH CH3CH2CH2CN [-CH(COOH)CH2COOH]2

122.25 69.11 234.16

1, 479 22, 252 2, 863

1.042 0.7936

1.529020 1.444020

CH3CH2CH2CH2SH CH3CH2CH(SH)CH3 HOCH2CH2CH(OH)CH2OH CH3CH2CH2CH2OH CH3CH2CH(OH)CH3 CH3CH2COCH3 CH3CH2C("NOH)CH3 CH3CH2CH"CH2 CH3CH"CHCH3 CH3CH"CHCH3 HOCH2CH"CHCH2OH HOCH2CH"CHCH2OH

90.19 90.19 106.12 74.12 74.12 72.11 87.12 56.11 56.11 56.11 88.11 88.11

1, 370 1, 373 1, 519 1, 367 1, 371 1, 666 1, 668 1, 203 13, 728 1, 205 12, 567 13, 2252

0.836725 4 0.824625 4 1.19020 0.809720 4 0.806920 4 0.805420 4 0.924 0.6255mp 4 0.6213 0.6041 1.070020 4 1.07020 4

1.443025 1.433825 1.474820 1.399320 1.397220 1.378820 1.442020 1.396220 1.3931⫺25 1.3848⫺25 1.478020 1.475520

⫺116 ⫺165

⫺185.3 ⫺139.3 ⫺105.8 2 25

98.5 85.0 19118mm 117.7 99.5 79.6 6015mm ⫺6.5 3.7 0.9 234 132

67.09 86.09 86.09

2, 408 2, 412 2, 408

0.834120 4 1.026720 4 0.960480 4

1.406020 1.448314 1.424877

⫺87 14–15 72

119 168–169 185

21

86.09 72.11

2, 407 1, 442

1.009120 4 0.866220 4

1.424920 1.434220

⫺39 ⫺89.4

163 123.6

65 56

⫺8

75–78

⫺112 196

⫺89.5 ⫺114.7 ⫺86.7

87

Solubility in 100 parts solvent

i aq; v s alc, eth i aq; v s alc, eth i aq; v s alc, eth s aq; v s alc v s aq, alc

INTERACTIVE

b462 b463

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

0.852420 4 0.863620 4 0.709514 0.992 1.100

1.490020

118.18 146.23

12, 519 13, 2085

0.901220 4 0.834

1.419820 1.401520

HOCH2CH2OCH2CH2OC4H9

162.23

12, 521

0.953620 20

1.430620

CH3CO2(CH2CH2O)2CH2CH2CH2CH3 CH3CO2CH2CH2O(CH2)3CH3 (CH3)3CO2CH2CH2OCH3

204.27

23, 308

0.978

160.22 132.20

23, 307 13, 2084

(CH3)3COCH2CH(OH)CH3

132.10

CH3(CH2)3O(CH2)3NH2 C4H9O2CH3

b502 b503 b504 b505

DL-sec-Butyl acetate tert-Butyl acetate tert-Butylacetic acid tert-Butyl acetoacetate

b506 b507 b507a b508 b509 b510 b511

2-Butylacrolein N-tert-Butylacrylamide Butyl acrylate tert-Butyl acrylate Butylamine (⫾)-sec-Butylamine tert-Butylamine

CH3CO2CH(CH3)C2H5 (CH3)3CO2CCH3 (CH3)CCH2COOH (CH3)3COC("O)CH2C("O)CH3 (CH3(CH2)3C("CH2)CHO H2C"CHCONHC(CH3)3 H2 "CHCO2(CH2)3CH3 H2C"CHCO2C(CH3)3 CH3CH2CH2CH2NH2 C2H5CH(NH2)CH3 (CH3)3CNH2

b493 b494 b495 b496 b497 b498 b499

1.129

1,4-Butanediol dimethanesulfonate, b210 Butanoic acid, b614 Butanoic anhydride, b615 trans-2-Butenal, c306

1.428920 1.408620 1.4161 1.554320

⬍⫺30

121.2 81.4 5.1 14913mm

56 ⫺6

2195mm

⬎110

⫺75

168 148

69 33

5 aq; s most org solv

⫺68.1

230.4

100

misc aq, alc, bz, acet, CCl4, PE

1.426020

245

⬎110

0.942 0.840

1.413620 1.398520

192 132

76 25

13, 2148

0.874

1.413020

143–145

44

73.14 116.16

43, 739 2, 130

0.853 0.881320 4

1.426020 1.394120

170 126

63 22

116.16 116.16 116.16 158.20

22, 131 2, 131 2, 337

0.874820 0.866520 4 0.912 0.954

1.388820 1.387020 1.411520 1.418020

112 95.1 190

31 16

112.17 127.19 128.17 128.17 73.14 73.14 73.14

14, 3482 44, 664 22, 388 23, 1228 4, 156 4, 160 4, 173

0.843

1.434820

Buten-4-carboxylic acid, p51 cis-2-Butenedioic acid, m1 2-Butene-1,1-diol diacetate, d28 trans-2-Buten-1-ol, c311

16.6 aq; misc alc v s aq, alc, acet, eth

⬎110

150

0.894 0.875 0.732725 4 0.72420 4 0.695120 4

1.418020 1.410820 1.399225 1.392820 1.378820

⫺77/⫺78 ⫺99 6–7

0.43 aq; misc alc, eth; s most org solvents 0.62 aq; s alc, eth i aq; misc alc, eth

60

128–129 ⫺64 ⫺50/⫺49 ⫺104 ⫺66

139

33

145 6360mm 77 63 44

39 17 ⫺12 ⫺9 ⫺9

Butopyronoxyl, b550 Butoxybenzene, b591 1-Butoxybutane, d148 Butyl alcohols, b473, b474, m385

0.14 aq20 misc aq, alc, eth misc aq, alc misc aq, alc

ROTATED

1, 442 1, 728 13, 1032 132, 226 102, 93 9,3, 4187

RIGHT

72.11 70.09 52.07 165.24 194.23 336.39

DEAN 37261 (McGHP)

CH3CH"CHCH2OH H2C"CHCOCH3 HC#CCH"CH2 CH3(CH2)3OC6H4NH2 CH3(CH2)3OC6H4COOH 2-[CH3(CH2)3O2CCH2O2C]C6H4CO2(CH2)3CH3 CH3(CH2)3OCH2CH2OH (CH3)3COCH2CH2OC2H5

b500 b501

trans-2-Buten-1-ol 3-Buten-2-one 1-Buten-3-yne 4-Butoxyaniline 4-Butoxybenzoic acid Butoxycarbonylmethyl butyl phthalate 2-Butoxyethanol 1-tert-Butoxy-2-ethoxyethane 2-(2-Butoxyethoxy)ethanol 2-(2-Butoxyethoxy)ethyl acetate 2-Butoxyethyl acetate 2-tert-Butoxy-2-methoxyethane 1-tert-Butoxy-2-propanol 3-Butoxypropylamine Butyl acetate

b487 b488 b489 b490 b491 b492

INTERACTIVE

H2NC6H4CO2(CH2)3CH3

193.25

b513

2-(tert-Butylamino)ethanol 2-(tert-Butylamino)ethyl methacrylate 3-(tert-Butylamino)1,2-propanediol 2-Butylaniline 2-sec-Butylaniline 4-Butylaniline 4-sec-Butylaniline 2-tert-Butylanthraquinone Butylbenzene sec-Butylbenzene tert-Butylbenzene Butyl benzoate 2-Butylbenzofuran 4-tert-Butylbenzoic acid 4-tert-Butylbenzoyl chloride N-(tert-Butyl)benzylamine tert-Butyl bromoacetate Butyl 2-butoxy-2hydroxyacetate Butyl butyrate Butyl carbamate Butyl carbazate 4-tert-Butylcatechol

(CH3)3CNHCH2CH2OH

117.19

H2C"C(CH3)CO2CH2CH2NC(CH3)3 (CH3)3CNHCH2CH(OH)CH2OH CH3(CH2)3C6H4NH2 C2H5CH(CH3)C6H4NH2 CH3(CH2)3C6H4NH2 C2H5CH(CH3)C6H4NH2

185.27

b515 b516 b517 b518 b519 b520

1.130

b521 b522 b523 b524 b525 b526 b527 b528 b529 b530 b531 b532 b533 b534

142, 249

44, 1509

Melting point,⬚C

5, 5, 5, 9,

(CH3)3CC6H4COOH

134.22 134.22 134.22 178.23 174.25 178.23

(CH3)3CC6H4COCl

196.68

C6H5CH2NHC(CH3)3

163.27

BrCH2CO2C(CH3)3

195.06

633 2721 503 635

0.953 0.957 0.945 0.977

Boiling point,⬚C

Flash point,⬚C

57–59

1748mm

42–45

9225mm

68

8210mm

71

1.442020 70

122, 123, 121, 122,

CH3(CH2)3OCH(OH)CO2(CH2)3CH3 CH3CH2CH2CCO2C4H9 H2NCO2(CH2)3CH3 H2NNHCO2C(CH3)3 (CH3)3C6H3-1,2-(OH)2

0.914

147.22 149.24 149.24 149.24 149.24 264.32

CH3CH2CH2CH2C6H5 C2H5CH(CH3)C6H5 (CH3)3CC6H5 C6H5CO2C4H9

Refractive index

1.538020 1.541020 1.535020 1.537020

Solubility in 100 parts solvent v sl s aq; s dil acids, alc, chl, eth

921mm 12312mm 12216mm 12015mm 245727mm

108 ⬎110 101 107

183 173 168.5 250

71 52 60 106 101

98–100 ⫺88 ⫺82.7 ⫺58.1 ⫺22

0.860420 4 0.860820 4 0.866920 4 1.000020 0.987 1.14220 4

1.489820 1.489020 1.492320 1.496 1.533020

1.007

1.536420

13520mm

87

12, 1022

0.881

1.496820

805mm

80

21, 96

1.321

1.445020

5010mm

49

20

40mm

90

74

166

49 108 91 151

413 414 415 112

9, 560

4

166.3

204.27

3 , 1497

0.996

1.4291

144.22 117.15 132.16 166.22

2, 271

0.869220 4

1.406420

1.04960 25

⫺91.5 53–55 39–42 52–55

misc alc, bz, eth misc alc, bz, eth misc alc, bz, eth i aq; s alc, eth i aq; v s alc, bz

650.03mm 285

i aq; misc alc, eth

0.2 aq;80 240 eth;25 s alc; v s acet

INTERACTIVE

Butyl-4-aminobenzoate

Density, g/mL

ROTATED

b512

Beilstein reference

LEFT

Name

b514

Formula

Formula weight

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

b536 b537 b538 b539 b540 b541 b542 b543 b544 b545 b546

1.131

b547 b548

tert-Butyl chloroacetate 4-tert-Butyl-1-chlorobenzene tert-Butylchlorodiphenylsilane Butyl chloroformate Butyl cyanoacetate tert-Butyl cyanoacetate Butylcyclohexane tert-Butylcyclohexane 2-tert-Butylcyclohexanol 4-tert-Butylcyclohexanol 2-tert-Butylcyclohexanone 4-tert-Butylcyclohexanone Butyl decyl ophthalate 4-sec-Butyl-2,6-di-tertbutylphenol

150.61

23, 444

1.053

1.423020

(CH3)3C6H4Cl

158.67

5, 416

1.006

1.510820

1.057

20

1.5675

900.02mm

⬎110

1.07425 4 0.993 0.972 0.818 0.831 0.902

1.411420 1.425420 1.420020 1.440020 1.447020

142 11515mm 108 178–180 167

25 87 91 41 42 79

d aq, alc; misc eth

11515mm

105

i aq

634mm

72

11620mm

96

(CH3)3CSi(C6H5)2Cl

274.87

ClCO2C4H9 NCCH2CO2C4H9 NCCH2CO2C(CH3)3 (C6H11)6C4H9 (C6H11)C(CH3)3 (CH3)3C(C6H10)OH

136.58 141.17 141.17 140.27 140.27 145.27

32, 11 21, 255

(CH3)3C(C6H10)OH

156.27

61, 18

(CH3)3C(C6H9)("O)

154.25

73, 143

(CH3)3C(C6H9)("O)

154.25

71, 29

C4H9O2C6H4CO2C10H21

362.51

C2H5CH(CH3)C6H2(OH)[C(CH3)3]

262.44

51, 20 51, 20 63, 126

4911mm 23–25

⫺78

0.896

217

43–46 62–70 1.456520 47–50

0.99425 25 6,3, 2094

46

i aq

i aq

202

0.902

25

Butyl carbitol, b495 Butyl cellosolve, b493 Butyl cellosolve acetate, b497 Butyl chloride, c75

14210mm

tert-Butyl chloride, c180 2-tert-Butyl-o-cresol, b574 2-tert-Butyl-p-cresol, b573 Butyl cyanide, p35

⬎110

RIGHT

Butyl bromide, b274 sec-Butyl bromide, b275 tert-Butyl bromide, b372 N-Butyl-1-butanamine, d139 Butyl butenoate, b531

ClCH2CO2C(CH3)3

DEAN 37261 (McGHP)

b535

ROTATED

b520

b525

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Name

b549 b550

N-Butyldiethanolamine Butyl 3,4-dihydro-2,2dimethyl-4-oxo-2Hpyran-6-carboxylate tert-Butyldimethylchlorosilane 6-tert-Butyl-2,4-dimethylphenol N-Butylethanolamine Butyl ethyl ether 2-Butyl-2-ethyl-1,5pentanediamine 2-Butyl-2-ethyl-1,3propanediol Butyl ethyl sulfide N-tert-Butylformamide Butyl formate Butyl glycidyl ether

b551 b552 b553 b554 b555

1.132

b556 b557 b558 b559 b560 b561

b563

Beilstein reference

Density, g/mL

Refractive index

0.98620 20 1.05425 25

1.462520 1.476720

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

⫺70

276 256–270

126 ⬎110

89

124–126

22

1.517820

23

249

111

0.8920 0.749520 4 0.876

1.44420 1.381820 1.470020

⫺3.5 ⫺124

192 92 269750mm

77 4 ⬎110

i aq; misc alc, eth

13, 2228

0.93150 20

1.458725

41–44

17850mm

⬎110

0.8 aq

118.24 101.15

13, 1522 43, 324

0.837620 4 0.903

1.449120 1.433020

⫺95.1 16

144.2 202

95

102.13

2, 21

0.892

1.388920

⫺91.5

106

18

O H2C 9 CHCH2OC(CH3)3

130.19

173, 988

0.917

1.416620

O (CH3)3CNHNH2 ·HCl

124.61

43, 1734

C4H9N(CH2CH2OH)2

161.25 226.27

4, 285

(CH3)3CSi(CH3)2Cl

150.73

4,4, 4076

(CH3)3CC6H2(CH3)2OH

178.28

63, 2020

HOCH2CH2NHC4H9 C4H9OC2H5 H2N(CH2)3C[(CH2)3CH3](C2H5)CH2NH2 HOCH2C(C2H5)(C4H9)CH2OH

117.19 102.18 186.34

1, 369

160.25

C4H9SC2H5 HCONHC(CH3)3 HCO2C4H9 H2C 9 CHCH2OC4H9

(CH3)3C9O9OH

C4H9NCO (CH3)3CNCO CH3CH(OH)CO2C4H9 CH3COCH2CH2CO2C4H9

3

43 194

20 4

20

90.12

1 , 1579

0.896

1.4007

124.19 99.13 99.13 148.19 172.22

232, 36

0.945 0.880 0.868 0.984 0.974

1.480020 1.406120 1.386520 1.421020 1.427020

4, 175 32, 207

s chl

⫺8

⫺28

3417mm

37

11612mm 115 86 185–187 1085.5mm

⬎110 17 ⫺4 69 91

s aq, alc, chl, eth

INTERACTIVE

b564 b565 b566 b567 b568

tert-Butylhydrazine HCl tert-Butyl hydroperoxide 1-Butylimidazole Butyl isocyanate tert-Butyl isocyanate Butyl lactate Butyl levulinate

Formula weight

ROTATED

b562

tert-Butyl glycidyl ether

Formula

LEFT

No.

b570 b571 b572 b573 b574 b575 b576 b577

1.133

b578 b579

Butyl 3-mercaptopropionate Butyl methacrylate sec-Butyl-2-methyl-2butenoate tert-Butyl methyl ether 2-tert-Butyl-4-methylphenol 2-tert-Butyl-5-methylphenol 2-tert-Butyl-6-methylphenol tert-Butyl-1-methyl-2propynyl ether tert-Butyl methyl sulfide Butyl nitrite tert-Butyl nitrite

HSCH2CH2CO2C4H9

162.25

H2C"C(CH3)CO2C4H9 CH3CH"C(CH3)CO2CH(CH3)C2H5 (CH3)3C9O9CH3

142.19 156.23

(CH3)3CC6H3(CH3)OH

164.25

(CH3)3CC6H3(CH3)OH

164.25

(CH3)3CC6H3(CH3)OH

164.25

(CH3)3COCH(CH3)C#CH

126.20

(CH3)3CSCH3

104.21

C4H9ONO (CH3)3CONO

103.12 103.12

1.410020

10112mm

93

23, 1286

0.88925 15 0.889

1.423025 1.435020

170 8527mm

50 66

i aq; misc alc, eth

1, 381

0.740420 4

1.368920

⫺109

52

⫺28

0.924775 4

1.496975

51.7

237

100

4.8 aq; v s alc, eth; unstable acid solns i aq; s org solv

0.964

1.519220

11812mm

105

230

107

4125mm

10

102

⫺3

v s alc

78 63

⫺13 ⫺13

misc alc, eth sl s aq; v s alc, chl, eth, CS2

62, 507

1.519020 0.795

1.410020

13, 1591

0.82620 4

1.44120

1, 369 1, 382

0.911404 0.867120 4

1.3768 1.368720

1,3-Butylene glycol, b456 1,4-Butylene glycol, b457 2,3-Butylene glycol, b458 1,3-Butyleneglycol methyl ether, m64 1,2-Butylene oxide, e3 Butyl ether, d148 Butyl ethyl ketone, h15 tert-Butyl fluoride, f22

30–32

⫺97.8

Butyl glycol, b493 2,2⬘-(Butylimino)diethanol, b549 Butyl iodides, i26, i27, i38 Butyl levulinate, b582 Butyl mercaptans, b470, b471; m394, m395, m396 Butyl methanoate, b559 Butyl methyl ketone, d572

RIGHT

Butyl diglyme, b151 tert-Butyldihydroxybenzene, b534 Butyl disulfide, d146 tert-Butyl disulfide, d147 1-Butylene, b477 cis-2-Butylene, b478 trans-2-Butylene, b479 1,4-Butylene bis(2,3-epoxypropyl) ether, b185

88.15

0.795

DEAN 37261 (McGHP)

b569

ROTATED

b550

b564

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued) Beilstein reference

Density, g/mL

Refractive index

0.855120 4 0.870415

1.442225 1.448025

0.973520 4 0.887

Name

b580 b581 b581a

Butyl 4-nitrobenzoate Butyl octadecanoate Butyl cis-9-octadecenoate Butyl 4-oxopentanoate 4-(1-Butylpentyl)pyridine

O2NC6H4CO2C4H9 CH3(CH2)16CO2C4H9 CH3(CH2)8CH"CH(CH2)7CO2C4H7 CH3C("O)CH2CH2CO2C4H9 C4H9CHC(CH2)3CH3

tert-Butyl peroxobenzoate 2-sec-Butylphenol 2-tert-Butylphenol 4-sec-Butylphenol 4-tert-Butylphenol tert-Butyl 4-phenoxyphenol ketone tert-Butyl phenyl carbonate Butyl phenyl ether 4-tert-Butylphenyl salicylate Butyl propionate tert-Butyl propionate 4-tert-Butyl pyridine tert-Butyl 1-pyrrolecarboxylate 1-Butylpyrrolidine 4-tert-Butylstyrene 1-Butyl-3-sulfanilylurea Butyltin trichloride Butyltin tris(2-ethylhexanoate)

C6H5C("O)O9O9C(CH3)3

194.23

CH3CH2CH(CH3)C6H4OH (CH3)3CC6H4OH CH3CH2CH(CH3)C6H4OH (CH3)3CC6H4OH C6H5OC6H4C("O)C(CH3)3

150.22 150.22 150.22 150.22 254.33

C6H5OC("O)OC(CH3)3

194.23

CH3CH2CH2CH2OC6H5 HOC6H4CO2CH6H4C(CH3)3

150.22 270.31

6, 143

CH3CH2CO2C4H9 CH3CH2CO2C(CH3)3 (CH3)3C(C5H4N) (C4H4N)CO2C(CH3)3

130.19 130.19 135.21 167.21

2, 241 23, 528 20, 252

0.881815 0.865 0.915 1.000

1.398225 1.393020 1.495220 1.468520

(C4H8N)C4H9 (CH3)3CC6H4CH"CH2 4-(H2N)C6H4SO2NHCONHC4H9 C4H9SnCl3 [CH3(CH2)3CH(C2H5)CO2]3SnC4H9

127.23 160.26 271.34

202, 4 53, 1254 14,4, 2667

0.814 0.875

1.444020 1.526020

282.17 605.43

44, 4346

1.693 1.105

1.522920 1.465020

b582 b583

b584

1.134

b585 b586 b587 b588 b589 b590

b597 b598 b599

203, 2872

Flash point,⬚C

1608mm 343

⬎110 160 180

1.427020 1.487720

1076mm 267

91 ⬎110

1.021

1.499020

760.2mm

93

0.982 0.978320 4 0.96920 4 114 0.9084

1.522220 1.522820 1.5150 1.4787114

228 221–224 13625mm 237 1753mm

112 ⬎110 115

790.8mm

101

⫺19 62–64

210.3

82 (OC)

⫺89

146.8 118 197 9220mm

38 20 63 75

157 929mm

36 80

9310mm

81 ⬎110

35–39 26.3 ⫺26

Solubility in 100 parts solvent

s alc; v s acet s eth s alc, acet, eth

C5H4N

62, 489 6, 522 6, 524 83, 491

1.047

1.480520

0.935120 4

1.497020

12 ⫺7 62 98 52–54

⫺37 143–145

i aq; s alc; v s eth s hot aq, alc, eth i aq; s alc, eth

⬎110

⬍0.1 aq; 79 alc; 153 EtOAc; 158 toluene v s alc, eth; v sl s aq

INTERACTIVE

b600 b601

172.22 205.35

92, 259 22, 352

Boiling point,⬚C

ROTATED

b593 b594 b595 b596

223.23 340.60 338.57

Melting point,⬚C

LEFT

b591 b592

Formula

Formula weight

No.

(CH3)3CC6H4CH3 C4H9SiCl3 (CH3)3CSiCl3

b608 b609 b610 b610a

4-tert-Butyltoluene Butyltrichlorosilane tert-Butyltrichlorosilane Butyl trifluoroacetate Butyltrimethoxysilane tert-Butyl trimethylsilyl peroxide Butylurea Butyl vinyl ether 5-tert-Butyl-m-xylene 1-Butyne

b610b b611

2-Butyne 2-Butyne-1,4-diol

CH3C#C9CH3 HOCH2C#CCH2OH

54.09 86.09

11, 261

b612

Butyraldehyde

CH3CH2CH2CHO

72.11

1, 662

b613 b614 b615

Butyramide Butyric acid Butyric anhydride

CH3CH2CH2CONH2 CH3CH2CH2COOH [CH3CH2CH2C("O)]2O

87.12 88.11 158.20

b616 b617

␤-Butyrolactone ␥-Butyrolactone

b618

Butyronitrile

b605 b606 b607

1.135

CF3CO2C4H9 C4H9Si(OCH3)3 (CH3)3C9O9O9Si(CH3)3

170.1 178.3 162.3

C4H9NHCONH2 C4H9OCH"CH2 (CH3)3CC6H3(CH3)2 CH3CH2C#CH

116.16 100.16 162.28 54.09

CH3CH2CH2CN

5, 439 4,1, 582 43, 1905

0.861220 1.160

22

1.491820 1.437020

⫺52 97–100

190 149 132–134

dec 135

100.1 164–165 4141mm

22

1.0268 0.931220 4 0.821920 4

1.353 1.397920 1.393520

0.779220 0.867 2.211 g/L 0.688

1.400720 1.494620

41, 371

96–98 ⫺92

68 45 40

⫺9 72

⫺126

94.2 205–206 8.1

1.45025

⫺32 56–58

27 238

152

0.801620 4

1.384320

⫺96/⫺99

74.8

⫺22

2, 275 2, 264 2, 274

0.958220 4 0.966820 4

1.399120 1.407020

116 ⫺5.3/⫺5.7 ⫺75/⫺66

216 163.5 199.5

72 54

86.09 86.09

171, 130 17, 234

1.056 1.12425 4

1.410920 1.434825

⫺43.5 ⫺43.5

204 204

60 98

69.11

22, 252

0.795415 4

1.444020

⫺112

117.6

24

5, 447

Butyl propyl ketone, o38 Butyl stearate, b581 Butyl sulfate, d169 Butyl sulfide, d170

tert-Butyl sulfide, d171 Butyl sulfite, d172 Butyl sulfone, d173 ␥-Butyrolactam, p285

s aq, alc, eth 0.3 aq

374 aq; 83 als; 0.04 bz; 2.6 eth; 70 acet 7.1 aq; misc alc, acet, eth, EtOAc 16 aq; s alc misc aq, alc, eth s aq (dec); alc (dec), eth misc aq; s alc, acet, bz, eth 3.3 aq; misc alc, eth

RIGHT

Butyl oleate, b581a tert-Butyl perbenzoate, b584 Butyl o-phthalate, d165 Butyl 2-propenoate, b507a

148.25 191.56 191.56

DEAN 37261 (McGHP)

b602 b603 b604

ROTATED

b616

b617

INTERACTIVE

No.

Name

b619 b620

Butyrophenone Butyryl chloride

c1

Formula

Beilstein reference

Density, g/mL

Refractive index 1.519520 1.41220

1.136

1.021 1.026321 4

Caffeine

194.19

26, 461

1.2318 4

c2 c3

(⫾)-Camphene (1R)-(⫹)-Camphor

136.24 152.24

5, 156 7, 101

0.842254 4 0.99225 4

c4

(1R,3S)-Camphoric acid

200.23

9, 745

1.18620 4

c5

(⫾)-10-Camphorsulfonic acid Carbazole

232.30

11, 314

167.21

20, 433

1.1018 4

182.22

10, 631

1.078

c9

4-Carbethoxy-2methyl-3-cyclohexen-1-one Carbobenzyloxyglycine Carbohydrazide

C6H5CH2OC("O)NHCH2COOH H2NNHC("O)NHNH2

c10

Carbon disulfide

c11

c7

c8

1.455154 1.5462

Boiling point,⬚C

11–13 ⫺89

230 102

238

subl 178

51–52 179

159 207

Flash point,⬚C 88 21

36 66

186–188

194 dec 245

1.488020

209.20

355

268–272

Solubility in 100 parts solvent

s aq (dec), alc (dec); misc eth 2.1 aq; 1.5 alc; 18 chl; 0.19 eth; 1 bz; 2 acet i aq; s alc, chl, eth 100 alc; 100 eth; 200 chl; 250 acet at 25⬚C: 0.8 aq, 100 alc, 250 acet, 200 eth, 200 HOAc; s chl deliq moist air; sl s HOAc, EtOAc; i eth 16 pyr; 11 acet; 3 eth; 0.8 bz; sl s HOAc, PE

⬎110

122 3, 121

CS2

76.14

3, 197

1.263220 4

Carbon monoxide

CO

28.01

Merck: 12, 1861

c12

Carbon oxide sulfide

COS

60.07

c13

Carbon tetrabromide

CBr4

331.65

1.145 g/L 2.456 g/L 3.42

1, 68

157–158

1.627020

⫺111.6

46.5

⫺205

⫺191.5

⫺138.8

⫺50

90

190

⫺30

none

v s aq; i alc, bz, eth; forms salts with acids 0.3 aq; misc bz, chl, eth, CCl4 2.3 aq; 16 alc; s chl, EtOAc, HOAc

INTERACTIVE

90.08

ROTATED

7, 313 2, 274

Melting point,⬚C

LEFT

148.21 106.55

c6

C6H5C("O)C3H7 CH3CH2CH2COCl

Formula weight

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Carbon tetrachloride

CCl4

153.82

1, 64

1.58925 25

c15

Carbon tetrafluoride

CF4

88.01

1, 59

c16 c17

Carbon tetraiodide 4-Carboxybenzenesulfonamide

CI4 HOOCC6H4SO2NH2

1.89⫺183 liq 4.3220 4

519.63 201.20

1, 74 11, 390

1.460720

1.137

c2

⫺183.6

⫺127.8

none

0.05 aq; misc alc, bz, chl, eth, CS2, PE

s bz, chl; dec hot alc v s alc; s alkalis; i aq, bz, eth

Carbazole, d751 Carbitol, e41a Carbitol acetate, e42 Carbobenzoxy chloride, b91 Carbolic acid, p65 3-Carbomethoxypropionyl chloride, m195 Carbon bromotrichloride, b432 N-Carbonylsulfamyl chloride, c249 Carbonyl sulfide, c12 Carboxybenzaldehyde, f37

c3

c4

RIGHT

c1

76.7

171 dec 280

Capronitrile, h61 Caproyl chloride, h72 Capryl alcohol, o32 Caprylaldehyde, o43 Caprylic acid, o30 Caprylonitrile, o28 Capryloyl chloride, o39 N-(Carbamoylmethyl)iminodiacetic acid, a14 Carbamylurea, b238 Carbanilide, d775

Cadaverine, p30 2-Camphanone, c3 Capraldehyde, d7 Capric acid, d15 Capric alcohol, d16 Caproaldehyde, h51 Caproic acid, h64 Caproic anhydride, h65 6-(or ⑀)-Caprolactam, o61 ⑀-Caprolactone, h69

⫺23

DEAN 37261 (McGHP)

c14

ROTATED

c5

c6

c7

INTERACTIVE

No. c18

Name

c20 c21

(4-Carboxybutyl)triphenylphosphonium bromide 1-(Carboxymethyl)pyridinium chloride R-(⫺)-Carvone Catechol

c22 c23

c19

Formula HOOC(CH2)4(C6H5)3Br

Formula weight

Beilstein reference

Refractive index

Melting point,⬚C

443.33

205–207

173.60

189 dec

1.138

7, 157

C6H5CH"CHCOC6H5

119.92 208.26

7, 478

c23a c24 c25 c26 c26a c27 c28

Chloroacetaldehyde 2-Chloroacetamide 2⬘-Chloroacetanilide 3⬘-Chloroacetanilide 4⬘-Chloroacetanilide Chloroacetic acid Chloroacetic anhydride

ClCH2CHO ClCH2CONH2 ClC6H4NHCOCH3 ClC6H4NHCOCH3 ClC6H4NHCOCH3 ClCH2COOH [ClCH2C("O)]2O

78.50 93.51 169.61 169.61 169.61 94.50 170.98

1, 610 2, 199 12, 559 12, 604 12, 611 2, 194 2, 199

c29

CH3COCH2CH2CONHC6H4Cl ClCH2CN C6H5COCH2Cl ClC6H4COCH3 ClC6H4COCH3 ClCH2COCl H2C"C(Cl)CN ClC6H3(CH3)NH2

211.65 75.50 154.60 154.60 154.60 112.94 87.51 141.60

2, 201 7, 282 71, 151 7, 281 2, 199

c38

4⬘-Chloroacetoacetanilide Chloroacetonitrile 2-Chloroacetophenone o-Chloroacetophenone p-Chloroacetophenone Chloroacetyl chloride 2-Chloroacrylonitrile 2-Chloro-4-aminotoluene 2-Chloroaniline

ClC6H4NH2

c39

3-Chloroaniline

ClC6H4NH2

0.96520 4 1.344

1.498920

⬍15 104–106

230 245

88 137

1.125 1.071262 4

1.507020

12 55–57

5050mm 20825mm

2 ⬎110

⫺16 119 88–90 79–81 179 61 46

85–86 225 dec

189 203

126

134

dec

160 (CC) 47 88 90 none 6 100

1.38520 4 1.580 (c) 1.549420 4

1.429765

1.422520

12, 988

1.193 1.32415 1.188 1.19220 4 1.42020 4 1.096 1.1671

1.543820 1.55520 1.454120 1.429020 1.584020

20–21 ⫺21.8 ⫺65 24–25

126 245 228738mm 237 106 89 238

127.57

12, 597

1.212520 4

1.589520

⫺14

208.8

97

127.57

12, 602

1.215022 4

1.593120

⫺10.4

230.5

123

54–56

Solubility in 100 parts solvent

i aq; misc alc 43 aq; v s alkalis, pyr; s alc, bz, chl, eth v s bz, chl, CS2, eth; sl s alc s aq, alc, eth 10 aq; 10 alc; sl s eth s alc v s alc, bz, CS2 i aq; v s alc, eth, CS2 v s aq; s alc, bz, eth v s chl, eth; sl s bz; dec by aq, alc

i aq; v s alc, bz, eth sl s aq; s eth i aq; misc alc, eth dec by aq, MeOH

0.88 aq; s acids, most common org solvents i aq; s most common org solvents

INTERACTIVE

Catecholborane Chalcone

Flash point,⬚C

ROTATED

150.22 110.11

Boiling point,⬚C

LEFT

C6H4-1,2-(OH)2

c30 c31 c32 c33 c34 c36 c37

Density, g/mL

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

4-Chloroaniline

c41

1-Chloroanthraquinone 2-Chloroanthraquinone 2-Chlorobenzaldehyde 3-Chlorobenzaldehyde 4-Chlorobenzaldehyde 2-Chlorobenzamide Chlorobenzene

c42 c43 c44 c45 c46 c47 c48 c49 c50

1.139

c51

4-Chlorobenzenesulfonamide 4-Chlorobenzenesulfonic acid 4-Chlorobenzenesulfonyl chloride 2-Chlorobenzoic acid

ClC6H4NH2

127.57

12, 607

242.66

1.16977 4

1.554685

72.5

232

7, 787

160

sublimes

242.66

7, 787

211

sublimes

ClC6H4CHO ClC6H4CHO ClC6H4CHO ClC6H4CONH2 C6H5Cl

140.57 140.57 140.57 155.58 112.56

7, 233 7, 234 7, 235 9, 336 5, 199

11 18 47 142–144 ⫺45.3

215 214 214

87 88 87

131.7

28

ClC6H4SO2NH2

191.64

11, 55

ClC6H4SO3H

192.62

11, 54

14922mm

107

ClC6H4SO2Cl

211.07

11, 55

14115mm

107

ClC6H4COOH

156.57

9, 334

1.248320 4 1.241 61 1.1964

1.5658 1.554520 1.55261

1.106320

1.524820

146

55 1.54420 4

140

sl s aq; s alc, bz, eth s aq; v s alc, bz, eth 0.049 aq30; v s alc, bz, chl, eth s hot aq, hot alc, hot eth

dec aq, alc; v s bz, eth 0.11 aq; v s alc, eth

Chloroacetaldehyde diethyl acetal, c96 Chloroacetaldehyde dimethyl acetal, c105 Chloroacetone, c229a Chloroenthranilic acid, a138 5-Chloroanthranilonitrile, a139 Chlorobenzeneamines, c38 thru c40 p-Chlorobenzenethiol, c252

RIGHT

Cetyl alcohol, h35 Cetyl bromide, b345 Chalcone, d768 Chloral, t218 Chloramine T, c258 Chloranil, t34, t35 Chlorendic anhydride, h28

(3-Carboxy-2-hydroxypropyl)trimentylammonium hydroxide, c19 (Carboxylmethyl)trimethylammonium hydroxide, b133 (Carbomethylimino)bis(ethylenenitrilo)-tetraacetic acid, d363 3-Carboxylpropyl disulfide, d809 Carvene, L17 Cellosolve, e40 Cellosolve acetate, e42

s hot aq; v s alc, acet, eth, CS2 sl s alc; s hot bz; misc eth sl s alc, bz; i eth

DEAN 37261 (McGHP)

c40

ROTATED

c19

c20

c22

c41

c42

INTERACTIVE

No. c52 c53 c54 c55 c56 c57 c58 c59

1.140

c60 c61 c62

c64 c65

c70

Beilstein reference

Density, g/mL

Refractive index

1.49625 4

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

158 241–243 46 93 44–47

232 223 300

77

19617mm

29

264

98

245

⬎110

⫺6.4

152

58

1.443825

⫺56.7

137.7

38

1.4463

⫺36

138.7

47

Solubility in 100 parts solvent

ClC6H4COOH ClC6H4COOH ClC6H4CN ClC6H4CN ClC6H4COC6H5

156.57 156.57 137.57 137.57 216.67

9, 337 9, 340 9, 336 9, 341 7, 419

ClC6H4COC6H5

216.67

7, 419

ClC6H4CCl3

229.92

5, 302

1.508

1.581720

ClC6H4CCl3

229.92

5, 303

1.495

1.572220

ClC6H4CF3

180.56

53, 692

1.354025

1.451325

ClC6H4CF3

180.56

53, 692

1.331125

ClC6H4CF3

180.56

1.35320

ClC6H4COC6H4COOH

260.68

10, 750

ClC6H4COCl

175.01

9, 336

1.382

1.571820

⫺3

238

⬎110

dec by aq & alc

ClC6H4COCl

175.01

9, 341

1.377

1.578020

14

222

105

dec by aq & alc

ClC6H4CH2OH ClC6H4CH2NH2 ClC6H4CH2NH2 ClC6H4CH2Cl

142.59 141.60 141.60 161.03

6, 444 12, 1073 12, 1074 5, 297

72 1.173 1.164 1.274

1.563020 1.558620 1.559120

⫺17

234 10411mm 215 214

88 90 82

ClC6H4CH2Cl

161.03

5, 308

30

222

97

ClC6H4CH2CN

151.60

9, 448

24

242

⬎110

108 ⬎110

s alc, acet, bz, eth

150

1.554020

0.04 aq; v s alc, eth 0.02 aq; v s alc, eth s alc, eth s alc, bz, chl, eth

s alc, bz, eth

v s alc, eth

s alc, v s eth

INTERACTIVE

c71

Formula weight

ROTATED

c66 c67 c68 c69

3-Chlorobenzoic acid 4-Chlorobenzoic acid 2-Chlorobenzonitrile 4-Chlorobenzonitrile 2-Chlorobenzophenone 4-Chlorobenzophenone 2-Chlorobenzotrichloride 4-Chlorobenzotrichloride 2-Chlorobenzotrifluoride 3-Chlorobenzotrifluoride 4-Chlorobenzotrifluoride 2-(4-Chlorobenzoyl)benzoic acid 2-Chlorobenzoyl chloride 4-Chlorobenzoyl chloride 4-Chlorobenzyl alcohol 2-Chlorobenzylamine 4-Chlorobenzylamine 2-Chlorobenzyl chloride 4-Chlorobenzyl chloride 2-Chlorobenzyl cyanide

Formula

LEFT

c63

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

c73 c74 c74a c75 c76 c77 c78 c79 c80

1.141

c81 c82 c83 c84 c85 c86 c87 c88 c89 c90

c96

Chlorocresol, c176, c177

151.60

9, 448

ClC6H4CH2SH

158.65

6, 466 3

1 , 949

30.3 1.589320

1.202 20 4

88.54 88.54 92.57 92.57 108.56 106.55 90.55 90.55

1.4712

1, 118 1, 119 12, 398 1, 669 12, 176 12, 176

0.9601 0.952 0.886420 4 0.873220 4 1.088320 4 1.055 0.942620 0.929

CH3CH(Cl)CH"CH2 CH3CO2CH2CH2CH2CH2Cl CH3CH(Cl)C#CH CH3CH(Cl)CH2COOH ClCH2CH2CH2COOH ClCH2CH2CH2CN ClCH2CH2CH2COCl

90.55 150.61 88.54 122.55 122.55 103.55 141.00

12, 174 22, 141 14, 970 2, 277 2, 278 2, 278 2, 278

0.900120 4 1.072 0.961 1.18620 4 1.223620 4 1.158 1.258

1.415520 1.433820 1.428020 1.442120 1.452120 1.441320 1.460920

ClCH2Si(CH3)2Cl

143.09

1.086

1.437320

H2C"C(CH2Cl)2

125.00

12, 181

1.080

1.475320

ClC6H4CH"CHCO2H

182.61

9, 594

ClC6H11 C6H11(CH2)3Cl

118.61 160.69

5, 21 52, 23

1.00020 4 0.997

1.462020 1.466220

C5H9Cl CH3(CH2)9Cl (C6H11)2BCl

104.58 176.73 212.57

5, 19 1, 168 164, 1637

1.005120 4 0.868 0.970

1.451220 1.436220

ClCH2CH(OC2H5)2

152.62

1, 611

1.018

1.415720

Chlorodibromomethane, d88

20

1.402120 1.397120 1.451820 1.417220 1.439020 1.439020

⬎110 76

20

H2C"CHCH"CHCl H2C"CHC(Cl)"CH2 CH3CH2CH2CH2Cl CH3CH2CH(Cl)CH3 ClCH2CH2CH2CH2OH CH3CH(Cl)C("O)CH3 CH3CH"CHCH2Cl CH3CH"CHCH2Cl

267

⫺123.1 ⫺131.3

16.3 12–16

⫺14

68 59 78.4 68.2 8920mm 117 84.1 85

⫺20

v s chl

⫺9 ⫺15 32 21 ⫺15 ⫺5

0.11 aq; misc alc, eth 0.1 aq; misc alc, eth s alc, eth v s alc, eth s alc, acet s alc, acet

65 9222mm 68–70 10917mm 19622mm 197 174

⫺20 64 1 ⬎110 ⬎110 85 72

v s acet

114752mm

21

138

36

142 795mm

28 78

i aq; s alc, eth

114 223 1011mm

15 83

i aq i aq

157

29

s alc, eth sl s aq; v s eth s alc, eth dec by aq, alc; s eth

208–210 ⫺44

⫺34

ROTATED

c93 c94 c95

ClC6H4CH2CN

RIGHT

c91 c92

4-Chlorobenzyl cyanide 4-Chlorobenzyl mercaptan 1-Chloro-1,3-butadiene 2-Chloro-1,3-butadiene 1-Chlorobutane 2-Chlorobutane 4-Chloro-1-butanol 3-Chloro-2-butanone cis-1-Chloro-2-butene trans-1-Chloro-2butene 3-Chloro-1-butene 4-Chlorobutyl acetate 3-Chloro-1-butyne 3-Chlorobutyric acid 4-Chlorobutyric acid 4-Chlorobutyronitrile 4-Chlorobutyryl chloride Chloro(chloromethyl)dimethylsilane 3-Chloro-2-chloromethyl-1-propene trans-2-Chlorocinnamic acid Chlorocyclohexane 1-Chloro-3-cyclohexylpropane Chlorocyclopentane 1-Chlorodecane Chlorodicyclohexylborane 2-Chloro-1,1-diethoxyethane

DEAN 37261 (McGHP)

c72

2-Chloro-N,N-diethylethylamine, d328

INTERACTIVE

No. c97 c98 c99 c100 c100a c101

1.142

c102 c103 c104

c107 c108

c110 c111 c112

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

ClCH2CH2CH(OC2H5)2

166.65

1, 632

0.995

1.424020

F2C(Cl)COOH

130.48

2, 201

1.540

1.355920

ClC6H3F2

148.54

54, 653

1.353

1.475020

CH3C(Cl)F2

100.50

13, 138

4.108 g/L

⫺131

⫺10

ClCH"CF2

98.48

4.025 g/L

⫺138.5

⫺18.5

HCClF2

86.47

13, 41

1.4909⫺69

⫺157

⫺40.8

0.30 aq

ClC6H3(OH)2

144.56

62, 818

107

14718mm

v s aq, alc, chl, eth

ClC6H3(OH)2

144.56

6, 849

101–102

263

v s aq; i alc, s eth

ClC6H3(OCH3)2

172.61

63, 4432

ClCH2CH(OCH3)2

124.57

ClC6H2(CH3)2NH2

155.63

12, 1125

ClC6H2(CH3)2OH

156.61

62, 463

(CH3)3CCH2Cl

106.59

1, 141

122.60

(CH3)2Si(Cl)H (CH3)2Si(Cl)CH"CH2

94.62 120.7

4,4, 4080

ClC6H2(NO2)2NH2

217.57

121, 367

36

122

none

127

32 0.19 aq

1.211

1.546720

234

110

1.09420 20

1.414820

130

28

1.110

0.86620 4

0.85220 4 0.88425 4

⬎110

38–40

1.404220 20

ClCH2C(CH3)2CH2OH

24–26

8425mm

Solubility in 100 parts solvent

115.5

246

⫺20

84.4 35mm

0.03 aq; 100 alc; s bz, eth, alkalis 32

1.4504

34–36

87

71

1.382720 1.41425

⫺111

36 82.5

⫺28 ⫺5

159

INTERACTIVE

c113

Formula weight

ROTATED

c109

3-Chloro-1,1-diethoxypropane Chlorodifluoroacetic acid 1-Chloro-2,4-difluorobenzene 1-Chloro-1,1-difluoroethane 1-Chloro-2,2-difluoroethylene Chlorodifluoromethane 1-Chloro-2,4-dihydroxybenzene 2-Chloro-1,4-dihydroxybenzene 2-Chloro-1,4-dimethoxybenzene 2-Chloro-1,1-dimethoxyethane 2-Chloro-4,6-dimethylaniline 4-Chloro-3,5-dimethylphenol 1-Chloro-2,2-dimethylpropane 3-Chloro-2,2dimethyl-1-propanol Chlorodimethylsilane Chlorodimethylvinylsilane 6-Chloro-2,4-dinitroaniline

Formula

LEFT

c105

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

c115 c116 c117 c118 c119 c120

1-Chloro-2,4-dinitrobenzene 2-Chloro-3,5-dinitrobenzoic acid Chlorodiphenylmethane Chlorodiphenylmethylsilane Chlorodiphenylphosphine 1-Chlorododecane 1-Chloro-2,3-epoxypropane

1.143

c122 c123

2-Chloroethanol 2-(2-Chloroethoxy)ethanol 2-[2-(2-Chloroethoxy)ethoxy]ethanol 2-Chloroethoxytrimethylsilane 2-Chloroethylamine hydrochloride 1-Chloro-2-ethylbenzene (2-Chloroethyl)benzene Chloroethylene N-(2-Chloroethyl)-Nethylamine 2-Chloroethyl ethyl ether

c124 c125 c126 c127 c128 c129 c130 c131

Chlorodimethyl ether, c173

5, 263

ClC6H2(NO2)2COOH

246.56

9, 415 2

1.498275 4

20 4

1.585760

20

52–54

315

186

198

241 explodes 1403mm

⬎110

C6H5CH(Cl)C6H5

202.68

5 , 500

1.140

1.5951

(C6H5)2Si(Cl)CH3

232.8

162, 606

1.127720 4

1.574220

295

⬎110

(C6H5)2PCl

220.64

16, 763

1.229

1.633820

320

⬎110

CH3(CH2)11Cl H2C 9 CHCH2Cl

204.79 92.53

17, 6

0.867320 4 1.181220 4

1.4426 1.435820

⫺9 ⫺57.2

116 116.1

93 31

v s alc; s bz 5.9 aq; misc alc, chl

64.52

1, 82

0.921404

1.374210

⫺139

12.3

⫺50

ClCH2CH2OH ClCH2CH2OCH2CH2OH

80.52 124.57

1, 337 1, 467

1.201920 1.180

1.442220 1.452920

⫺67.5

128.6 815mm

60 90

0.45 aq0; 48 alc; misc eth misc aq, alc

ClCH2CH2OCH2CH2OCH2CH2OH ClCH2CH2OSi(CH3)3

168.62

1, 468

1.160

1.458020

1205mm

107

152.70

43, 1856

0.944

1.414020

134

30

ClCH2CH2NH2 ·HCl

115.99

4, 133

ClC6H4C2H5

140.61

179.2

66

i aq; misc alc, eth

C6H5CH2CH2Cl

140.61

5, 354

1.069

1.530020

8416mm

66

s alc, bz, eth

H2C"CHCl C6H5N(C2H5)CH2CH2Cl

62.50 183.68

1, 186 123, 263

0.97⫺14 1.075

⫺13.4 16442mm

⫺78 ⬎110

sl s aq; s alc

1.558420

ClCH2CH2OCH2CH3

108.57

1, 337

0.989

1.412020

107

15

O CH3CH2Cl

146 ⫺81

1.05525 25

2-Chloroethyl alcohol, c122

17

sl s alc; s hot alc, bz, eth 0.3 aq

⫺154

2-Chloroethyl ether, b163

ROTATED

Chloroethane

202.55

RIGHT

c121

ClC6H3(NO2)2

DEAN 37261 (McGHP)

c114

INTERACTIVE

No. c132

Name

Formula

Chloroform-d 1-Chloroheptane 1-Chlorohexadecane

c133a c134 c135 c136

1.144

c137 c138 c139

c141 c142 c143 c144

Refractive index

1.035

1.409020

186.08

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

90

15

9815mm

100

1530.3mm

⬎110

Solubility in 100 parts solvent

186

156.61

63, 675

184.11

20, 17

CH3C6H4SO3CH2CH2Cl

234.70

112, 45

1.294

1.529020

H2C"CHOCH2CH2Cl

106.55

12, 473

1.052515 15

1.437020

⫺69.7

110

16

0.6 aq

ClC6H4F

130.55

51, 110

1.244

1.501020

⫺42.4

138.5

31

s alc, eth

ClC6H4F

130.55

1.219

1.494420

126

20

s alc, eth

Cl(F)C6H3CH2Cl

179.02

1.401

1.537220

93

FC6H4C("O)CH2CH2CH2Cl

200.64

1.220

1.525520

⬎110

Cl(F)C6H3NO2

175.55

51, 130

1.602817

1.567417

41.5

12717mm

Cl(F)C6H3OH

146.55

64, 880

1.344

1.5300

23

884mm

75

Cl(F)C6H3CH3

144.58

1.191

1.502620

156

46

20

C6H5OCH2CH2Cl

4

1.129

1.534020 236

743mm

Cl(F)C6H3CH3

144.58

5 , 813

1.186

1.4998

158

CHCl3

119.39

1, 61

1.483220

1.445920

⫺63.6

61.1

CDCl3 CH3(CH2)6Cl CH3(CH2)15Cl

120.39 134.65 260.89

13, 63 1, 154 1, 172

1.500 0.88116 0 0.865

1.444520 1.425020 1.449020

⫺64 ⫺69

60.9 159–161 1491mm

LEFT

c140

1, 337

Density, g/mL

51

41 ⬎110

0.50 aq25; misc alc, bz, eth, PE, CCl4 see under chloroform misc alc, eth

INTERACTIVE

c146 c147 c148

c133

94.54

Beilstein reference

ROTATED

ClCH2CH2OCH3

c145

2-Chloroethyl methyl ether N-(2-Chloroethyl)morpholine HCl 2-Chloroethyl phenyl ether N-(2-Chloroethyl)piperidine HCl 2-Chloroethyl ptoluenesulfonate 2-Chloroethyl vinyl ether 1-Chloro-2-fluorobenzene 1-Chloro-3-fluorobenzene 2-Chloro-6-fluorobenzyl chloride 4-Chloro-4⬘-fluorobutyrophenone 3-Chloro-4-fluoronitrobenzene 2-Chloro-4-fluorophenol 2-Chloro-6-fluorotoluene 4-Chloro-2-fluorotoluene Chloroform

Formula weight

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

c152 c153 c154 c155 c156 c157 c158

1.145

c159 c160 c161 c162

0.878020 4 1.204

1.419520 1.456020

⫺94

1-Chlorohexane 6-Chloro-1-hexanol 4-Chloro-4⬘-hydroxybenzophenone 5-Chloro-8-hydroxy7-iodoquinoline 5-Chloro-8-hydroxyquinoline 1-Chloro-4-iodobenzene 1-Chloro-3-iodopropane 1-Chloro-3-mercapto2-propanol Chloromethane

CH3(CH2)5Cl Cl(CH2)6OH ClC6H4C("O)C6H4OH

120.62 136.62 232.67

1, 143 82, 187

175–178

305.50

21, 98

172

179.61

21, 95

130

ClC6H4I

238.46

5, 221

1.18657 4

Cl(CH2)3I

204.44

1, 114

1.904

HSCH2CH(OH)CH2Cl

126.61

13, 2156 1, 59

3-Chloro-4-methoxyaniline 5-Chloro-2-methoxyaniline 1-Chloro-2-methoxybenzene 5-Chloro-2-methoxybenzoic acid 2-Chloro-6-methoxypyridine

ClC6H3(OCH3)NH2

157.60

13, 511

50–55

ClC6H3(OCH3)NH2

157.60

13, 383

83–85

ClC6H4OCH3

142.59

6, 184

ClC6H3(OCH3)COOH

186.59

10, 103

CH3O(Cl)(C5H3N)

143.57

CH3Cl

50.49

26 98

i alc, eth; 0.8 chl; 0.6 HOAc sl s aq HCl 227

108

1.546320

170–172

⬎110

1.277

1.527620

571.3mm

97

2.064 g/L

1.3712⫺24

⫺24.2

⬍0

53–54

⫺97.7

1.544520

1.123

i aq sl s aq; v s alc, eth

s alc

0.48 aq;25 s alc,; misc chl, eth, HOAc

110

196

76

i aq; s alc, eth

98–100 1.526320

1.207

186

1-Chloro-3-hydroxypropane, c231

5-Chloro-2-hydroxyaniline, a147 Chlorohydroxybenzoic acids, c245, c246

RIGHT

2-Chloro-6-fluorobenzal chloride, t238 ␣-Chloro-4-fluorotoluene, f16

134 11014mm 25713mm

DEAN 37261 (McGHP)

c149 c150 c151

ROTATED

c133

c134

c152

c153

INTERACTIVE

2-Chloro-6-methylaniline 3-Chloro-2-methylaniline 3-Chloro-4-methylaniline 4-Chloro-2-methylaniline 5-Chloro-2-methylaniline 3-(Chloromethyl)benzoyl chloride DL-4-Chloro-2-(␣methylbenzyl)phenol 1-Chloro-3-methylbutane 2-Chloro-2-methylbutane Chloromethyldichloromethylsilane Chloromethyl ethyl ether 3-(Chloromethyl)heptane Chloromethyl methyl ether Chloromethyl methyl sulfide 1-(Chloromethyl)naphthalene 4-Chloro-2-methylphenol

c164 c165 c166 c167 c168

1.146

c169

c169a c170 c171 c172 c172a c173 c174 c175 c176

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

CH3O(Cl)C6H3NH2

141.60

121, 388

1.152

1.576120

2

215

98

CH3O(Cl)C6H3NH2

141.60

12, 836

1.185

1.587420

2

11710mm

⬎110

CH3O(Cl)C6H3NH2

141.60

12, 988

1.583020

25

238

100

CH3O(Cl)C6H3NH2

141.60

12, 835

1.584820

27

241

99

CH3O(Cl)C6H3NH2

141.60

12, 835

1.584020

22

237

160

ClCH2C6H4COCl

189.04

92, 325

1.330

1.574820

15020mm

⬎110

C6H5CH(CH3)C6H3(Cl)OH

232.71

64, 4710

1.238

1.599420

1552mm

⬎110

ClCH2CH2CH(CH3)CH3

106.60

0.875020

1.408420

⫺104

99

⬍21

sl s aq; misc alc, eth

CH3CH2CCl(CH3)2

106.59

1, 134

0.865020 4

1.405220

⫺73.7

85

⫺9

i aq; s alc, eth

ClCH2Si(Cl)2CH3

163.5

43, 1888

1.286

1.449420

121

110

12, 645

1.0420 4

1.404020

79–83

19

0.876920

1.431920

172

60

1.070320 4

1.396120

57–59

15

1.153

1.496320

105

17

1.180

1.638020

32

16925mm

⬎110

45–48

220–225

⬎110

ClCH2OCH2CH3 CH3CH2CH2CH2CH(CH2Cl)CH2CH3 ClCH2OCH3

94.54 148.68 80.51

1, 580

ClCH2SCH3

95.48

C10H7CH2Cl

176.65

5, 566

CH3(Cl)C6H3OH

142.59

6, 359

⫺103.5

s alc

s hot alc

s alc; v s eth

dec by aq; s acet, CS2

sl s aq

INTERACTIVE

c163

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

c178 c179 c180 c181 c182 c183 c184

1.147

c185 c186 c187 c188 c189 c190

4-Chloro-3-methylphenol 1-Chloro-2-methyl-2phenylpropane 1-Chloro-2-methylpropane 2-Chloro-2-methylpropane 1-Chloro-2-methylpropene 3-Chloro-2-methylpropene Chloromethyltrimethylsilane 6-(Chloromethyl)uracil 1-Chloronaphthalene 2-Chloronaphthalene 4⬘-Chloro-3⬘-nitroacetophenone 2-Chloro-4-nitroaniline 2-Chloro-5-nitroaniline 4-Chloro-2-nitroaniline

CH3(Cl)C6H3OH

142.59

6, 381

C6H5C(CH3)2CH2Cl

168.67

52, 320

65–68 1.524020

1.047

235

i aq; s alc, bz, chl, eth, acet

9610mm

92

(CH3)2CHCH2Cl

92.57

1, 124

0.8829

1.4010

⫺130.3

68.9

⬍21

0.09 aq; misc alc, eth

(CH3)3CCl

92.57

1, 125

0.842020

1.385620

⫺26

50.8

⬍0

sl s aq; misc alc, eth

(CH3)2C"CHCl

90.55

1, 209

0.918620 4

1.422520

68.1

⫺1

misc alc, eth

ClCH2C(CH3)"CH2

90.55

1, 209

0.921015 4

1.427220

72

⫺12

misc alc, eth

122.67

43, 1844

0.886120 4

1.418020

99

⫺2

160.56

231, 328

C10H7Cl C10H7Cl ClC6H3(NO2)C("O)CH3

162.62 162.62 199.60

5, 541

259 256

121

73, 995

⫺2.3 60 101

ClC6H3(NO2)NH2

172.57

12, 733

107–109

ClC6H3(NO2)NH2

172.57

12, 732

119–121

ClC6H3(NO2)NH2

172.57

12, 729

117–119

ClCH2Si(CH3)3

⫺80

257 dec 1.193820 4 1.137771

␣-Chloronitrotoluene, n45

15

1.632620 1.607971

s alc, bz, PE s alc, bz, chl, eth

sl s aq; v s alc, eth

v s alc, eth

Chloronitro-␣,␣,␣-trifluorotoluenes, c199, c200

RIGHT

Chloromethylbenzenes, b90, c255, c256, c257 (Chloromethyl)oxirane, c120

15

DEAN 37261 (McGHP)

c177

ROTATED

c184

INTERACTIVE

4-Chloro-3-nitroaniline 1-Chloro-2-nitrobenzene 1-Chloro-3-nitrobenzene 1-Chloro-4-nitrobenzene 2-Chloro-4-nitrobenzoic acid 2-Chloro-5-nitrobenzoic acid 4-Chloro-3-nitrobenzoic acid 4-Chloro-3-nitrobenzophenone 2-Chloro-5-nitrobenzotrifluoride 4-Chloro-3-nitrobenzotrifluoride 4-Chloro-2-nitrophenol 2-Chloro-6-nitrotoluene 4-Chloro-2-nitrotoluene 1-Chlorooctadecane 1-Chlorooctane 1-Chloropentane 3-Chloro-2,4-pentanedione 5-Chloro-2-pentanone 3-Chloroperoxybenzoic acid

c192 c193 c194 c195 c196

1.148

c197 c198 c199 c200 c201 c202 c203 c203a c204 c204a c205 c206 c207

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

99–101

Solubility in 100 parts solvent

ClC6H3(NO2)NH2

172.57

12, 731

v s alc; s eth

ClC6H4NO2

157.56

5, 241

1.348

33

246

123

s alc, bz, eth

ClC6H4NO2

157.56

5, 243

1.53420 4

44

236

103

sl s alc; v s chl, eth

ClC6H4NO2

157.56

5, 243

1.520

83–84

242

⬎110

sl s alc; v s eth, CS2

ClC6H3(NO2)COOH

201.57

9, 404

ClC6H3(NO2)COOH

201.57

9, 403

ClC6H3(NO2)COOH

201.57

9, 402

ClC6H3(NO2)C("O)C6H5

261.66

71, 230

ClC6H3(NO2)CF3

225.55

1.527

1.508320

ClC6H3(NO2)CF3

225.55

1.511

1.489320

ClC6H3(NO2)OH ClC6H3(NO2)CH3

173.56 171.58

6, 238 5, 327

1.537770

ClC6H3(NO2)CH3

171.58

5, 327

CH3(CH2)17Cl CH3(CH2)7Cl CH3(CH2)4Cl CH3COCH(Cl)COCH3

288.95 148.68 106.60 134.56

13, 566 1, 159 1, 130 1, 785

0.849 0.875 0.882020 1.129

1.451620 1.429820 1.411520 1.483020

ClCH2CH2CH2COCH3 ClC6H5C(O)OOH

120.58 172.57

12, 738 94, 972

1.057118 4

1.439020

139–141

s hot aq, hot bz

1.60818

166–168

sl s aq; s alc, bz, eth

1.64518

180–183

sl s alc; s hot aq

104–106

23513mm 231

98

⫺2.5

222

101

85–87 36

238

125

i aq

39

240718mm

⬎110

i aq

⫺58 ⫺99

1581.5mm 182 107–108 5218mm

⬎110 70 13 12

7220mm

35

69–71

0.02 aq; misc alc, eth

s acet, eth

INTERACTIVE

c191

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

2-Chlorophenol

ClC6H4OH

128.56

6, 183

1.257323 4

1.556520

9.8

175

63

c209 c210

3-Chlorophenol 4-Chlorophenol

ClC6H4OH ClC6H4OH

128.56 128.56

6, 185 6, 186

1.24545 4 1.223878 4

1.556540 1.547940

33 43

214 220

⬎110 115

c211

4-Chlorophenoxyacetic acid 2-(4-Chlorophenoxy)2-methylpropanoic acid (⫾)-2-(4-Chlorophenoxy)propanoic acid 4-Chlorophenylacetic acid (4-Chlorophenyl)acetonitrile 2-Chloro-1,4-phenylenediamine sulfate 4-Chloro-1,2-phenylenediamine 1-(4-Chlorophenyl)ethanol 3-Chlorophenyl isocyanate 4-Chlorophenyl isocyanate 4-Chlorophenyl phenyl sulfone

ClC6H4OCH2COOH

186.59

6, 187

157–159

ClC6H4OC(CH3)2COOH

214.65

Merck: 12, 2437

118–119

ClC6H4OCH(CH3)COOH

200.62

63, 695

117

ClC6H4CH2COOH

170.60

9, 448

108

ClC6H4CH2CN

151.60

9, 448

30.5

H2NC6H3(Cl)NH2 · H2SO4

240.67

13, 117

251–253

s aq

ClC6H3(NH2)2

142.59

13, 25

70–73

s mineral acids

ClC6H4CH(CH3)OH

156.61

61, 236

1.171

1.541O20

ClC6H4NCO

153.57

12, 606

1.260

1.557620

ClC6H4NCO

153.57

12, 616

1.200

1.561820

ClC6H4SO2C6H5

252.72

61, 149

1-Chloro-3-phenylpropane 4-Chlorophenyl sulfone

C6H5(CH2)3Cl

154.64

5, 391

(ClC6H5)2SO2

287.17

6, 327

c212

c213 c214 c215 c216

1.149

c217 c218 c219 c220 c221

c223

4-Chlorophenyl sulfone, b171

265–267

⬎110

11910mm

⬎110

⫺4.4

11443mm

86

29–31

204

⬎110

94

1.080

at 20⬚C: 74 acet; 44 bz; 5 CCl4; 65 diox; 21 i-PrOH

1.520720

219 145–148

87

25010mm

4-Chlorophenyl sulfoxide, b172

ROTATED

p-Chlorophenacyl bromide, b286 Chlorophenylamines, c38, c39, c40

v s aq, alc, eth; s bz

RIGHT

c222

sl s aq; v s alc, eth, caustic alkali sl s aq; s alc, eth sl s aq; v s alc, chl, eth, CHCl3, glyc s aq; MeOH

DEAN 37261 (McGHP)

c208

INTERACTIVE

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

171, 162 1, 104 1, 105

0.889920 0.856320

1.388620 1.377720

3-Chloro-1,2-propanediol 2-Chloropropanoic acid 3-Chloropropanoic acid 1-Chloro-2-propanol 3-Chloro-1-propanol Chloro-2-propanone

ClCH2CH(OH)CH2OH

110.54

1, 473

1.321820 4

CH3CH(Cl)COOH

108.52

2, 248

1.182

ClCH2CH2COOH

108.52

2, 249

CH3CH(OH)CH2Cl ClCH2CH2CH2OH ClCH2COCH3

94.54 94.54 92.53

1, 363 1, 356 1, 653

1.11520 1.130920 4 1.13515

ClCH2CH2CN

89.53

2, 250

1.144318

c241

3-Chloropropanonitrile 3⬘-Chloropropanophenone 2-Chloropropanyl chloride 3-Chloropropanyl chloride 3-Chloro-1-propene 3-Chloropropylacetate 3-Chloropropyl thiolactate (3-Chloropropyl)triethoxysilane (3-Chloropropyl)trimethoxysilane 3-Chloropropyne

c242

2-Chloropyridine

Cl(C5H4N)

c227 c228 c229

1.150

c230 c231 c232 c233 c234 c235 c236

c239 c240

Solubility in 100 parts solvent

15010mm 46–47 35–36

⫺31 ⫺35

1.480520

213

⬎110

0.27 aq; misc alc, eth 0.2 aq20; misc alc, bz, chl, eth s aq, alc, eth

1.434520

170–190

101

misc aq, alc, eth

41

200765mm

⬎110

v s aq, alc, chl; s eth

1.437520 4 1.445020 1.432020

51 73 27

misc aq; s alc

⫺44.5

126–127 160–162 119.7

1.434120

⫺51

9550mm d ⬎ 130 12414mm

75 ⬎110

58 ⫺122.8 ⫺117

10 aq; misc alc, chl, eth

ClC6H4C("O)CH2CH3

168.62

73, 1028

CH3CH(Cl)COCl

126.97

2, 248

1.308

1.440020

109–111

31

dec aq, alc

ClCH2CH2COCl

126.97

2, 250

1.330713

1.457020

143–145

61

ClCH2CH"CH2 CH3CO2(CH3)3Cl CH3C("O)SCH2CH2Cl

76.53 130.02 152.64

1, 198 4, 148 23, 493

0.93820 4

1.415420

45

⫺32

i aq; d hot aq, hot alc; s alc; v s eth 0.36 aq; misc alc, PE

1.159

1.494620

45–47

20 4

⫺134.5 148–150

8410mm

20

77

10mm

Cl(CH2)3Si(OC2H5)3

240.81

1.009

1.420

102

Cl(CH2)3Si(OCH3)3

198.72

1.07725 4

1.418325

195750mm

78

57

⫺13

166714mm

65

ClCH2C#CH

74.51

1, 248

1.030625 4

1.456020

113.55

20, 230

1.20515

1.532020

ROTATED

c236a c237 c238

Flash point,⬚C

⫺78

misc alc, bz, eth, EtOAc sl s aq; s alc, eth

INTERACTIVE

168.58 78.54 78.54

3-Chlorophthalide 1-Chloropropane 2-Chloropropane

Boiling point,⬚C

LEFT

CH3CH2CH2Cl CH3CHClCH3

c224 c225 c226

Melting point,⬚C

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

3-Chloropyridine 4-Chlororesorcinol 4-Chlorosalicylic acid 5-Chlorosalicylic acid N-Chlorosuccinimide

Cl(C5H4N) ClC6H3-1,3(OH)2 ClC6H3(2-OH)COOH ClC6H3(2-OH)COOH

c248

Chlorosulfonic acid

c249 c250 c251 c252 c253 c254 c255

1.151

c256 c257 c258

c259

1.530020

113.55 144.56 172.57 172.57 133.53

20, 230 62, 818 10, 101 10, 102 21, 380

1.194

ClHO3S

116.52

Merck: 12, 2218

1.75320 4

1.43714

⫺80

152755mm

none

Chlorosulfonyl isocyanate 1-Chlorotetradecane 2-Chlorothiophene 4-Chlorothiophenol 8-Chlorothiophylline Chlorotitanium triisopropoxide 2-Chlorotoluene

ClSO2NCO

141.53

1.626

1.447020

⫺44

107

none

CH3(CH2)13Cl Cl(C5H3S) ClC6H4SH

12, 135 17, 32 6, 326 26, 473

0.859 1.286

1.446020 1.548320

1424mm 127–129 205–207

⬎110 22 ⬎110

[(CH3)2CHO]3TiCl

232.84 118.59 144.62 214.61 260.62

ClC6H4CH3

126.59

5, 290

1.082620 4

1.526820

⫺35.6

159.0

47

3-Chlorotoluene 4-Chlorotoluene N-Chloro-p-toluene sulfonamide, sodium salt 4-(4-Chloro-o-tolyloxy)butyric acid

ClC6H4CH3 ClC6H4CH3 CH3C6H4SO2NCl⫺ Na⫹

126.59 126.59 227.67

5, 291 5, 292

1.076019 4 1.069720 4

1.521820 1.515020

⫺47.8 7.5 167 dec

161.8 162.4

50 49

ClC6H3(CH3)O(CH2)3COOH

228.68

1.65

⫺72 49–52 dec 290

148 14718mm

65

1.4 aq; 0.67 alc; 2 bz; sl s chl, CCl4, eth s pyr, dichloroethane; aq dec with violence

i aq; misc alc, eth s alkali

1.091

22 sl s aq; v s alc, bz, chl, eth s alc, bz, chl; misc eth sl s aq; s alc, bz, eth s aq; i bz, chl, eth

99–100

␣-Chlorotoluene, b90 Chlorotoluidines, c163 thru c167

3-Chloropropylene-1,2-oxide, c120 1-Chloro-2,5-pyrrolidinedione, c247

RIGHT

Chloroprene, c236a ␤-Chloropropionaldehyde diethyl acetal, c97

106–108 210–212 172 150–151

DEAN 37261 (McGHP)

c243 c244 c245 c246 c247

ROTATED

c224

c247

c253

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

c260 c261 c262

c269 c270 c271 c272 c273 c274

Chlorotriethylgermane Chlorotriethylsilane Chloro-2,2,2-trifluoroethane Chlorotrifluoroethylene Chlorotrifluoromethane Chlorotrimethylgermane Chlorotrimethylsilane Chlorotriphenylmethane Chlorotriphenyltin Chloro-tris(dimethylamino)silane ␣-Chloro-o-xylene ␣-Chloro-m-xylene ␣-Chloro-p-xylene 2-Chloro-p-xylene 4-Chloro-p-xylene Cholesterol

c275

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index 1.459020 1.430020 1.30900

195.23 150.73 118.5

43, 1912 4, 624 1,3, 138

1.175 0.898 1.3890

CF2 "CFCl

116.47

13, 646

ClCF3

104.46

13, 42

(CH3)3GeCl

153.16

(CH3)3SiCl (C6H5)3CCl

108.64 278.78

4,3, 1857 5, 700

(C6H5)3SnCl [(CH3)2N]3SiCl

385.46 195.8

12, 914

CH3C6H4CH2Cl CH3C6H4CH2Cl CH3C6H4CH2Cl ClC6H3(CH3)2 ClC6H3(CH3)2

140.61 140.61 140.61 140.61 140.61 386.66

5, 364 5, 373 5, 384 5, 384 5, 363 6,3, 2607

Cholic acid

408.58

103, 2162

c276 c277 c278

Cinchonine 1,8-Cineole trans-Cinnamaldehyde

C6H5CH"CHCHO

194.40 154.25 132.16

232, 369 17, 23 7, 348

0.92125 25 1.05025 25

c279

trans-Cinnamic acid

C6H5CH"CHCOOH

148.16

9, 573

1.247544

c263 c264 c265

1.152

c266 c267 c268 c268a

Boiling point,⬚C

⫺105

142–144 6.9

1.315

⫺158.2

⫺28

4.270 g/L

⫺181

⫺81

Flash point,⬚C ⬎110 29

1.238222

1.428320

⫺13

102

1

0.858020 4

1.387020

⫺40 110–112

57 23520mm

⫺27

108 dec

24014mm 6312mm

0.97520 4

1.44220

1.063 1.06420

1.539120 1.535020 1.533020 1.524020 1.528020

1.049 1.047 1.05219 19

v s bz, chl, eth

9625mm 195–196 200 186 221–223 2030.5mm

73 75 75 57 66

ca. 260 1 ⫺7.5

176.4 13620mm

48 71

133

300

4.5 2 148.5 198

1,457220 1.621920

Solubility in 100 parts solvent

i aq; misc alc, eth i aq; misc alc, eth misc alc, bz, eth, acet misc alc, bz, eth, acet 1.3 alc; 35 eth; 22 chl; s bz, PE (15⬚): 0.03 aq; 3.1 alc; 2.8 acet; 15.2 HOAc; 0.5 chl; 0.036 bz 1.6 alc; 0.9 chl; 0.2 eth misc alc, chl, eth 0.014 aq; misc alc, chl, eth 0.05 aq; 16 alc; 8 chl

INTERACTIVE

(C2H5)3GeCl (C2H5)3SiCl CF3CH2Cl

Melting point,⬚C

ROTATED

Name

LEFT

No.

166.61

92, 390

1.161725 4

1.61443

35–36

258

⬎110

CH3CO2CH2CH"CHC6H5 C6H5CH"CHCH2OH

176.22 134.18

62, 527 6, 570

1.0571 1.039735 35

1.542120 1.575833

33

265 250.0

⬎110 ⬎110

c283 c284

Cinnamyl chloride Citraconic acid

C6H5CH"CHCH2Cl CH3C(COOH)"CHCOOH

159.62 130.10

5, 482 2, 768

1.096 1.62

1.584020

⫺19 92 dec

10812mm

79

c285 c286

Citraconic anhydride Citral (geranial plus neral, cis and trans forms, resp.)

112.08 152.24

17, 440

1.247 0.888

1.471220 1.487620

8

(CH3)2C"CHCH2CH2C(CH3)"CHCHO

214 229

␣⬘-Chloro-␣,␣,␣-trifluoro-m-xylene, t304 Chlorotrihexylsilane, t307 Chloroxylenol, c109 Chromone, b55

2-Chlorotriethylamine, d328 2-Chloro-2-(trifluoromethyl)aniline, a141 Chloro-␣,␣,␣-trifluorotoluenes, c60, c61, c62 4-Chloro-␣,␣,␣-trifluoro-o-toluidine, a142

s hot alc, CCl4

s aq; v s common organic solvents v s aq, alc, eth; sl s chl; i bz, PE

101 101

DEAN 37261 (McGHP)

C6H5CH"CHCOCl

c281 c282

trans-Cinnamoyl chloride Cinnamyl acetate Cinnamyl alcohol

c280

Chrysene, b52 Cinchophen, p153 Citral, d644, d645

1.153 c276

c275

RIGHT

c274

ROTATED

c277

c285

INTERACTIVE

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

0.890

1.454020

Melting point,⬚C

Boiling point,⬚C

1.154

198.31

14, 3570

155.11

22, 254

192.12

3, 556

1.665

156.27

11, 232

0.857020 4

Cocaine

303.35

222, 150

c300

Coumarin

146.15

17, 328

c301

Creatine

131.14

4, 363

c302 c303

Creatinine o-Cresol

CH3C6H4OH

113.12 108.14

24, 245 6, 349

1.027341

1.536141

255 dec 30

191

81

c304

m-Cresol

CH3C6H4OH

108.14

6, 373

1.03420 4

1.543820

12

202.2

86

c305

p-Cresol

CH3C6H4OH

108.14

6, 389

1.017941

1.531241

34.8

201.9

86

c306 c307

trans-Crotonaldehyde Crotonic acid

CH3CH"CHCHO CH3CH"CHCOOH

70.09 86.19

1, 728 2, 408

0.851620 0.96484

1.437320 1.422880

⫺76 71.6

102–104 185

13 87

c308 c309 c310 c311 c312 c313

Crotonic anhydride Crotononitrile Crotonyl chloride Crotyl alcohol Crotyl chloride 12-Crown-4

(CH3CH"CHO)2O CH3CH"CHCN CH3CH"CHCOCl CH3CH"CHCH2OH CH3CH"CHCH2Cl

154.17 67.09 104.54 72.11 90.55 176.21

2, 411 2, 412 2, 411 1, 442 12, 176

1.040 1.419020 1.091 0.845 0.929 1.089

1.474020 1.419020 1.460020 1.427020 1.436020 1.463020

248 121 120–123 122 85 700.5mm

110 20 35 37 ⫺5 ⬎110

c287

Citral dimethyl acetal

c288

Citrazinic acid

c289

Citric acid

c290

␤-Citronellol

c299

(CH3)2C"CHCH2CH2C(CH3)"CH(OCH3)2

HOOCCH2C(OH)(COOH)CH2COOH (CH3)2C"CHCH2CH2CH(CH3)CH2CH2OH

HOOCCH2N(CH3)C("NH)NH2

10610mm

Flash point,⬚C 92

carbonizes without melting ⬎300 154 1.456020 1.502298

0.93520 4

Solubility in 100 parts solvent

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

i aq; s alkali

59 aq 222

98

1870.1mm

68–70

298

98

v sl s aq; misc alc, eth 0.17 aq; 15 alc; 140 chl; 28 eth; s acet; EtOAc, CS2 0.25 aq; v s alc, chl, eth; s alkali 1.3 aq; 0.11 alc; i eth

dec 303

LEFT ROTATED

8 aq; sl s alc; i eth 3.1 aq40; misc alc, chl, eth; s alkali 2.5 aq40; misc alc, chl, eth; s alkali 2.3 aq40; misc alc, chl, eth; s alkali 18.1 aq20 54.6 aq20; 52.5 EtOH25; 53 acet; 37.5 toluene

17 aq; misc alc

INTERACTIVE

specific for Li⫹

18-Crown-6 Crystal Violet Cumene hydroperoxide

C6H5C(CH3)2OH

264.32 407.99 152.20

13, 756 63, 1814

1.030

1.521020

1018mm

Crotononitrile, b482 trans-Crotonyl alcohol, c311 Crotyl alcohols, b486, b487 Crotyl bromide, b276 Crotyl chloride, c79

Cleland’s reagent, d484 2,4,6-Collidine, t393 p-Coumaric acid, h109 Cresylic acids, c303, c304, c305 trans-Crotonic acid, b484

⬎110

42–45 215 dec

12-Crown-4, t124 15-Crown-5, p46 Cumene, i103 Cumic alcohol, i104

56

DEAN 37261 (McGHP)

c314 c315 c316

1.155 c288

c299

c300

c302

RIGHT ROTATED

c313

c314

c315

INTERACTIVE

No.

Name

Formula

Formula weight

Density, g/mL

Refractive index

1.156

c316a c317 c318

Cumylphenol Cupferron Cyanamide

C6H5C(CH3)2C6H4OH C6H5N(NO)O⫺ NH+4 H2NCN

c319 c320 c321

2-Cyanoacetamide Cyanoacetic acid Cyanoacetohydrazide

NCCH2CONH2 NCCH2COOH NCCH2C("O)NHNH2

c322

Cyanoacetylurea

127.10

c323 c324 c325 c326

2-Cyanoethanol 2-Cyanoethyl acrylate Cyanogen bromide 1-Cyano-3-methylisothiourea, sodium salt 1-Cyanonaphthalene 2-Cyanopyridine 3-Cyanopyridine 4-Cyanopyridine Cyanotrimethylsilane Cyanuric acid

NCCH2C("O)NHC("O)NH2 NCCH2CH2OH H2C"CHCO2CH2CH2CN BrCN CH2NH("NCN)S⫺ Na⫹

2, 589 2, 583 Merck: 11, 2688 3, 66

71.08 125.13 105.93 137.14

32, 213 33, 543 3, 39 4, 71

1.05880 1.052 2.01520 4

1.447020

C10H7CN NC(C5H4N) NC(C5H4N) NC(C5H4N) (CH3)3SiCN

153.18 104.11 104.11 104.11 99.21 129.08

9, 649 22, 36 22, 41 22, 46 44, 3893 26, 239

1.111325 25 1.081

1.629818 1.528820

0.78320 4 1.7680

1.392420

C4H8 (C4H7)COOH

56.10 100.12

5, 17 9, 5

0.70380 1.047

1.37520 1.443320

C10H20 C12H23OH C12H22("O)

140.27 184.32 182.31 162.28

0.871

1.470720

c335 c336 c337 c338

(C12H23)NH2

166.31 183.34

72, 48 54, 1115

74–76 163–164 46

83380mm

119.5 66 115

10815mm dec

Flash point,⬚C

Solubility in 100 parts solvent

335 ⬎110 215 107

v s aq, alc 78 aq; 29 BuOH; 42 EtOAc; s alc, eth 25 aq; 3.1 alc s aq, alc, eth; sl s bz v s aq; s alc; i eth

214 dec

52 290 dec

0.90662 0.892520 4

1.507020

0.863

1.482220

38 26–28 50–52 78–80 11–12 ⬎360; dec to HOCN ⫺91 ⫺20 to ⫺7.5

10811mm 10812mm 61–62

103 5

299 215 201

89 84

118–119

1

misc aq, alc; sl s eth v s aq, alc, eth

i aq; v s alc, eth s aq; v s alc, bz, eth v s aq, alc, bz, eth s aq, alc, bz, eth 0.5 aq; s hot alc, pyr; i acet, bz, chl, eth

13 195

83

i aq; v s alc, acet

201

65

77 59–61 ⫺18

851mm 231

87

28–30

232–245 1247mm

93 121

INTERACTIVE

c339 c340

Cyclobutane Cyclobutanecarboxylic acid Cyclodecane Cyclododecanol Cyclododecanone trans,trans,cis-1,5,9cyclododecatriene Cyclododecene Cyclododecylamine

1.28220 4

Boiling point,⬚C

ROTATED

c333 c334

84.08 85.06 99.09

161, 395 32, 63

Melting point,⬚C

LEFT

c327 c328 c329 c330 c331 c332

212.29 155.16 42.04

Beilstein reference

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

c345 c346 c347 c348 c349 c350 c351 c352

98.18 114.19 112.17 92.13

5, 29 6, 10 7, 13 5, 280

0.81120 4 0.94820 4 0.949020 4 0.888

1.445520 1.476020 1.461120 1.521120

C7H12

96.17 236.40

5, 65 73, 521

0.824

1.458520 1.489020

C6H12

84.16

5, 20

0.778620 4

1.426220

C6D12 C10H10(NHCH3)2

92.26 142.25

53, 36

0.893 0.945

C6H11CN

109.17

9, 9

C6H11COCl

146.62

C6H11CHO

112.17

1.157

Cycloheptane Cycloheptanol Cycloheptanone 1,3,5-Cycloheptatriene Cycloheptene 8-Cyclohexadecene-1one Cyclohexane

C7H14 C7H13OH C7H12("O)

Cyclohexane-d12 1,3-Cyclohexanebis(methylamine) 1,3-Cyclohexanecarbonitrile Cyclohexanecarbonyl chloride Cyclohexanecarboxaldehyde

118 185 179–181 115.5

6 71 55 26

v s alc, eth sl s aq; v s alc, eth i aq; v s alc; s eth s alc, eth; v s bz, chl

114.7 19519mm

⫺6 ⬎110

s alc, eth

80.7

⫺20

0.01 aq; misc acet, alc, bz, CCl4, eth

1.421020 1.493020

78

⫺18 106

0.919

1.450520

7616mm

65

9, 9

1.096

1.470020

184

66

7, 19

0.926

1.450020

163

40

1-Cyanopropane, b468a 2-Cyano-1-propene, m30a 2-Cyanotoluene, t184 4-Cyanotoluene, t185 Cyanuric chloride, t255 1,5-Cyclododecadiene-9,10-epoxide, e4

⫺75.3

6.6

Cyclododecane epoxide, e5 Cycloheptanone isooxime, a307 Cycloheptyl bromide, b310 2,5-Cyclohexadien-1,4-dione, b58 2,5-Cyclohexadiene-1,4-dione with 1,4-benzenediol (1:1), q1 Cyclohexaneacetic acid, c373

RIGHT

Cupron, b50 Cyanoacetonitrile, m5 Cyanoanilines, a121, a122, a123 Cyanobenzene, b51 2-Cyanoethanol, h173 Cyanoethylene, a63 Cyanomethane, a29

⫺8.0 2

DEAN 37261 (McGHP)

c341 c342 c343 c344

ROTATED

c332

c338

c339

c344

c346

INTERACTIVE

c353

Cyclohexanecarboxylic acid trans-1,2-Cyclohexanediamine 1,3-Cyclohexanedicarboxylic acid cis-1,2-Cyclohexanedicarboxyic anhydride 1,4-Cyclohexanedimethanol 1,4-Cyclohexanedivinyl ether 1,4-Cyclohexanediol 1,3-Cyclohexanedione 1,2-Cyclohexanedione dioxime Cyclohexanemethylamine Cyclohexanepropionic acid Cyclohexanethiol Cyclohexanol Cyclohexanone Cyclohexanone oxime Cyclohexene

c354 c355 c356 c357 c358

1.158

c359 c360 c361 c362 c363 c364 c365 c366 c367 c368 c369 c370 c371 c372

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

C6H11COOH

128.17

9, 7

1.048015 4

1.453020

29

232.5

⬎110

C6H10(NH2)2

114.19

133, 8

0.951

1.488420

14–15

9218mm

68

C6H10(COOH)2

172.18

9, 732

132–141

154.17

17, 452

32–34

15817mm

⬎110

43

283

161

12614mm

⬎110

15020mm

65

C6H10(CH2OH)2

144.21

0.978100 4

1.489320

C6H10(OCH"CH2)2

196.29

0.919

1.472020

C6H10(OH)2 C6H8("O)2 C6H8("NOH)2

116.16 112.13 142.16

6, 741 7, 554 72, 526

1.086191

1.4576102

C6H11CH2NH2

113.20

12, 12

0.870

1.463020

C6H11CH2CH2COOH

156.23

9, 82

0.912

1.463620

C6H11SH C6H11OH C6H10("O) C6H10("NOH) C6H10

116.23 100.16 98.15 113.16 82.15

6, 8 6, 5 7, 8 7, 10 5, 63

0.950 0.941630 0.947820 4

1.492120 1.462930 1.451020

0.809420 4

1.446420

3

98–100 103–105 185–188

C6H9CH2OH

112.17

6 , 215

0.961

1.4853

C6H8("O)

98.15 96.13 159.23

17, 21 72, 55 203, 3239

0.970 0.993 1.021

1.452020 1.488520 1.548020

43

14–17

275.8

⬎110

25.4 ⫺31 89–91 ⫺103.5

158–160 161 155.7 206–210 83.0

43 68 44

CH3CO2C6H11

142.20

6, 7

0.966

1.439520

18mm

⫺53

0.21 aq; s alc, bz, eth

misc aq, alc; 2.5 eth

s aq, alc, acet, chl s aq 145–147

20

Solubility in 100 parts solvent

⫺12

3.8 aq25; misc alc, bz 15 aq10; s alc, eth s aq, eth; sl s alc 0.02 aq; misc alc, bz, acet, eth

85

76

130 168 14120mm

27 56 ⬎110

v s alc

173

57

sl s aq; s org solv

INTERACTIVE

c373

3-Cyclohexene-1methanol Cyclohexene oxide 2-Cyclohexene-1-one 4-(3-Cyclohexene-1yl)pyridine Cyclohexyl acetate

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

c378 c379 c380 c381 c382 c383 c384 c385

1.159

c386

Cyclohexylacetic acid Cyclohexylamine Cyclohexylbenzene Cyclohexyldimethoxymethylsilane 2-Cyclohexylethanol Cyclohexylethyl acetate N-Cyclohexylformamide Cyclohexyl isocyanate Cyclohexyl isothiocyanate Cyclohexyl methacrylate Cyclohexylmethanol 3-Cyclohexyl-1propanol N-Cyclohexyl-2pyrrolidinone

242–244 134 240 201.2

⬎110 31 98 73

207745mm 9815mm

86 81

11310mm

⬎110

1.455120 1.535020

168–170 219

48 95

0.964

1.458020

704mm

82

6, 14 61, 15

0.921525 4 1.007

1.464025 1.497520

181 218

71 101

213, 3149

1.026

1.495

284

⬎110

C6H11CH2COOH C6H11NH2 C6H11C6H5 C6H11Si(OCH3)2CH3

142.20 99.18 160.26 188.35

92, 9 12, 5 5, 503

1.007 0.867120 0.950220 4 0.940

1.463020 1.459320 1.525820 1.439020

C6H11CH2CH2OH CH3CO2CH2CH2C6H11

128.22 170.25

6, 17

0.919 0.949

1.464720 1.4461

C6H11NHCHO

127.18

122, 11

C6H11NCO C6H11NCS

125.17 141.24

122, 12 122, 12

0.980 0.996

H2C"C(CH3)CO2C6H11

168.24

63, 25

C6H11CH2OH C6H11CH2CH2CH2OH

114.19 142.24 167.25

38–40

12

cis-4-Cyclohexene-1,2-dicarboxylic anhydride, t81 N-(1-Cyclohexen-1-yl)morpholine, m465 N-(1-Cyclohexen-1-yl)pyrrolidine, p284 Cyclohexyl alcohol, c365 Cyclohexyl bromide, b311

misc aq, alc, chl, eth i aq; v s alc, eth

s alc, eth

Cyclohexyl chloride, c91 Cyclohexyl ketone, c366 Cyclohexyl mercaptan, c364 Cyclohexylmethane, m202 Cyclohexylmethyl bromide, b367

RIGHT

Cyclohexanecarboxylic acid chloride, c351 Cyclohexaneethanol, c378 Cyclohexaneethyl acetate, c379 Cyclohexanemethanol, c384 Cyclohexanone cyanohydrin, h112 cis-4-Cyclohexene-1,2-dicarboximide, t82

31–33 ⫺18 7

DEAN 37261 (McGHP)

c374 c375 c376 c377

ROTATED

c356

c370

c386

INTERACTIVE

c372

No. c387 c388 c389 c390 c391 c392 c393 c394 c395

1.160

c396 c397

c403

c406 c407

C8H15OH C8H14("O) C8H14 C8H15NH2

Beilstein reference

Density, g/mL

Refractive index

Boiling point,⬚C

Flash point,⬚C

5534mm

24

1.490525 1.457420 1.498020

⫺53 to ⫺51 ⫺69 14.8 32

149–150 151.1 940.5mm

31 30 ⬎110

0.974020 4 0.958420 4 0.846 0.928 0.802120 4

1.485020 1.649420 1.469820 1.480420 1.446316

14–15 41–43 ⫺16 ⫺48 ⫺85

10822mm 195–197 145–146 190 41–42

86 72 25 62

108.18

54, 401

0.869

1.492820

108.18 112.22 144.21

5, 116 5, 35 63, 4094

0.881825 4 0.834 1.080

128.22 126.20 110.20 127.23 66.10

62, 25 7, 21 51, 35 Merck: 12, 2807

Melting point,⬚C

Cyclopentane Cyclopentanecarboxylic acid Cyclopentanol Cyclopentanone Cyclopentanone oxime Cyclopentene 2-Cyclopentene-1acetic acid N-(1-Cyclopenten-1yl)morpholine Cyclopentylamine 3-Cyclopentylpropanoic acid Cyclopropane

C5H10 C5H9COOH

70.13 114.14

5, 19 9, 6

0.746020 4 1.05320 4

1.406820 1.454020

⫺94 4

49.3 216

⫺37 93

C5H9OH C5H8("O) C5H8("NOH) C5H8 C5H7CH2COOH

86.13 84.12 99.13 68.11 126.16

6, 5 7, 5 7, 7 5, 61 9, 42

0.948820 4 0.950918 4

1.452120 1.436620

0.772020 1.047

1.422820 1.467520

⫺19 ⫺51 53–55 ⫺135.1 19

140 130.6 196 44.2 942.5mm

51 26 92 ⫺29 ⬎110

0.957

1.510520

10612mm

60

1.448220 1.457020

106–108 13012mm

17 46

Cyclopropanecarbonitrile Cyclopropanecarbonyl chloride

153.23 C5H9NH2 C5H9CH2CH2COOH

85.15 142.20

12, 4

0.863 0.996

C3H6

42.08

5, 15

0.7204⫺79

C3H5CN

67.09

9, 4

0.91116

1.420720

135

32

104.54

9, 4

1.152

1.452220

119

23

C3H5COCl

⫺127

⫺32.8

Solubility in 100 parts solvent

s CCl4

misc alc, bz, CCl4, eth; s aniline, HOAc, CS2 i aq; misc alc, eth sl s aq; s MeOH sl s aq; s alc sl s aq; misc alc, eth s aq, alc, bz, chl, eth

37 mL/100 mL aq15; v s alc, eth s eth

INTERACTIVE

c408

C8H16 C8H14(OH)2

Formula weight

ROTATED

c404 c405

cis,cis-1,3-Cyclooctadiene 1,5-Cyclooctadiene Cyclooctane trans-1,2-Cyclooctanediol Cyclooctanol Cyclooctanone cis-Cyclooctene Cyclooctylamine Cyclopentadiene

Formula

LEFT

c398 c399 c400 c401 c402

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

c410 c411 c412 d1 d2

Cyclopropanecarboxylic acid Cyclopropyl methyl ketone L-Cysteine L-Cystine

d7 d8 d9 d10

1,9-Decalene cis-Decahydronaphthalene trans-Decahydronaphthalene Decahydro-2-naphthol Decamethylcyclopentasiloxane Decamethyltetrasiloxane Decanal Decane 1,10-Decanediamine Decanedioic acid

d11 d12

1,2-Decanediol 1,10-Decanediol

d3 d4 d5 d6

C3H5COOH

86.09

9, 4

1.088

1.438020

C3H5COCH3

84.12

7, 7

0.899320 4

1.424020

17–19

182–184

71

sl s hot aq; s alc, eth

114

21

s aq, alc, eth

1.161

HSCH2CH(NH2)COOH HOOCCH(NH2)SSCH2CH(NH2)COOH H2C"CH(CH2)6CH"CH2 C10H18

121.16 240.30

4, 506 4, 507

220 dec dec 240

138.25 138.25

11, 123 5, 92

0.750 0.896320 4

1.432020 1.481020

⫺43

169 195.8

41 58 (CC)

C10H18

138.25

52, 56

0.870020 4

1.469020

⫺30.4

187.3

54

v s alc, chl, eth; misc most ketones, esters see under cis

C10H17OH [9Si(CH3)2O9]5

154.25 370.78

6, 67 44, 4128

0.996 0.959320 4

1.50020 1.398220

⫺38

10914mm 10120mm

⬎110 72

i aq

(CH3)3SiO[Si(CH3)2O]2Si(CH3)3 H(CH2)9CHO CH3(CH2)8CH3 H2N(CH2)10NH2 HOOC(CH2)8COOH

310.69

43, 1879

0.853620 4

1.389520

⫺68

194

62

sl s alc; s bz, PE

156.27 142.29 172.32 202.25

1, 711 1, 168 4, 273 2, 718

0.83015 4 0.730120 4

1.428020 1.411020

i aq; s alc, eth 0.07 aq

1.422134

208–209 174.1 14012mm 23210mm

85 46

1.20720 4

⫺5 ⫺29.7 62–63 134.5

CH3(CH2)7CH(OH)CH2OH HO(CH2)10OH

174.28 174.28

1, 494 12, 560

48–50 74

255 1708mm

⬎110 ⬎110

0.1 aq20, eth17; v s alc, esters, ketones

cis-Decalin, d2 trans-Decalin, d3 Decamethylene glycol, d12 Decanealdehyde, d7 1,10-Decanedicarboxylic acid, d805

sl s aq, eth; v s alc

RIGHT

Cymenes, i118 thru i120 Cysteamine, a161 Cytosine, a194 p,p⬘-DDT, b173 1,2-Decahydroacenaphthylene, a2

Cyclopentanepropanoic acid, c405 Cyclopentene oxide, e42 Cyclopentyl bromide, b313 Cyclopentyl chloride, c93 Cyclopropyl bromide, b314 Cyclopropyl cyanide, c407

v s aq, alc; i bz, eth 0.01 aq; s acid, alkali; i alc

DEAN 37261 (McGHP)

c409

ROTATED

c387

c388

c395

c403

INTERACTIVE

1.162

1.121220 4 0.829515 4 0.841 0.875250 4

1,467820 1.429520 1.456520 1.428840

158.29 170.25 156.27 156.27 156.27 190.71 140.27 157.30

1, 425 175,9, 91 1, 711 11, 367 1, 711 2, 356 13, 858 4, 199

0.829720 4 0.954 0.825 0.825 0.82420 0 0.919 0.740820 0.787

1.435920 1.458020 1.425020 1.424120 1.423720 1.441020 1.421020 1.436020

285.48 168.15

124, 3005 17, 559

C6H5CH2COC6H5 (CH3)2Si(OOCCH3)2

196.25 176.3

72, 368

(CH3CO2)2CHCH"CHCH3

172.18

(CH3CO2)2CHCH"CH2 (H2C"CHCH2)2NH (H2C"CHCH2)2O H2C"CHCH2O2CCH"CHCO2CH2CH"CH2 C6H4(CO2CH2CH"CH2)2 (H2C"CHCH2)2S [-CH(OH)CONHCH2CH"CH2]2

Decanedioyl dichloride Decanenitrile 1-Decanethiol Decanoic acid

ClC("O)(CH2)8COCl CH3(CH2)8CN CH3(CH2)9SH CH3(CH2)8COOH

239.14 153.27 174.35 172.27

d16 d17 d18 d19 d20 d21 d22 d23

1-Decanol ␦-Decanolactone 2-Decanone 3-Decanone 4-Decanone Decanoyl chloride 1-Decene Decylamine

CH3(CH2)9OH

d24 d25

Dehydroabeitylamine Dehydroacetic acid

d26 d27

Deoxybenzoin Diacetoxydimethylsilane trans-1,1-Diacetoxy2-butene 1,1-Diacetoxy-2propene Diallylamine Diallyl ether Diallyl maleate

d28 d29 d30 d31 d32 d33 d34 d35

Diallyl 1,2-phthalate Diallyl sulfide (⫹)-N,N-Diallyltartardiamide

CH3(CH2)7COCH3 CH3(CH2)6COC2H5 CH3(CH2)6C("O)(CH2)2CH3 CH3(CH2)8COCl H(CH2)8CH"CH2 H(CH2)10NH2

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

22075mm 235–237 11413mm 270

⬎110

⫺34.5 ⫺66 12–14

232 1200.02mm 211 205 207 965mm 170.6 216–218

82 ⬎110 71 25 71 106 47 85

111–113

270

55–56

⫺15 ⫺26 32 6.9 3.5 ⫺3.8

98 ⬎110

Solubility in 100 parts solvent dec aq, alc misc alc, chl, eth 0.015 aq; s alc, bz, chl, CS2 i aq; s alc, eth

i aq; misc alc, eth dec aq. alc; s eth i aq; misc alc, eth sl s aq; misc alc, bz, eth, acet

⬎110

1.546020

1.20104 1.05420 4

320 164–166

110

1.403020

2, 154

1.057

1.429020

10620mm

87

158.16

2, 154

1.078

1.419020

184

78

97.16 98.15 196.20

4, 208 1, 438 23, 1926

0.787 0.80518 0 1.073

1.440520 1.416020 1.470220

112 94–95 1164mm

15 ⫺6 (OC) ⬎110

246.27 114.21 228.25

93, 4120 1, 440 4, 218

1.121 0.887727 4

1.518720 1.488920

1675mm 138

⬎110 46

⫺88 ⫺47

⫺85 186–188

at 25⬚: 22 acet; 18 bz; 5 eth; 3 EtOH; 5 MeOH i aq; v s alc, eth

i aq; misc alc, eth

sl s aq; misc alc, eth

INTERACTIVE

2, 719 2, 356 12, 459 22, 309

d13 d13a d14 d15

Beilstein reference

ROTATED

Refractive index

Name

LEFT

Density, g/mL

Formula

Formula weight

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

d37 d38 d39 d40

1,2-Diaminoanthraquinone 1,4-Diaminoanthraquinone 1,5-Diaminoanthraquinone 2,6-Diaminoanthraquinone 3,5-Diaminobenzoic acid

(H2N)2C6H3COOH

238.25

141, 459

289–291

sl s alc, eth

238.25

14, 197

265–269

sl s aq, alc; v s bz

238.25

14, 203

308 dec

238.25

14, 215

⬎325

152.15

14, 453

228

Delphinic acid, m184 Dextrose, g8 Diacetone alcohol, h150 1,2-Diacetoxyethane, e137 (Diacetoxyiodo)benzene, i24

Decyl alcohol, d16 Decyl bromide, b315 Decyl chloride, c94 Decylic acid, d15 Decyl iodide, i29 Decyl mercaptan, d14

sl s hot aq, pyr ⫺H2O, 110

sl s aq; s alc, eth

DEAN 37261 (McGHP)

d36

Diacetyl, b466 Diacetylmethane, p34 Diallyl, h39 (⫹)-N,N⬘-Diallyltartramide, d35 2,5-Diaminoanisole, m103

1.163 d24

d25

d36

RIGHT

d17

ROTATED

d37

d38

d39

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No. d41 d42 d43 d44 d45

1.164 d46 d47

d49

d52

d53

Beilstein reference

Density, g/mL

Refractive index 1.456920

H2N(CH2)4NH2 H2NC6H4NHC6H4NH2 · H2SO4

88.15 297.33

4, 264 13, 110

0.877

C6H10(NH2)2

114.19

133, 8

0.951

C6H10(NH2)2

114.19

C6H10[N(CH2COOH)2]2 · H2O

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

27.3 300

158–160

14–15

8115mm

68

131, 3

69–72

197

71

364.36

133, 10

213–216

H2NC6H4CH2C6H4NH2

198.27

13, 238

91–92

H2NC6H4SO2C6H4NH2

248.30

13, 426

170–173

i aq; s alc, bz

H2NC6H4SO2C6H4NH2

248.30

13, 536

175–176

126.12

24, 469

285 dec

i aq; s alc, acet, dil HCl s aq

108.10 170.30

42, 949 13, 4

NCC(NH2)"C(NH2)CN

CH3N[(CH2)3NH2]2

CH3CH(NH2)CH2NH2 H2N(CH2)3NH2

4

1.288620

0.914

1.480520 20

145.25

4 , 1279

0.901

187.21

261, 69

1.4025 4

74.13 74.13

4, 257 4, 261

0.878 0.888

178–179 ⫺45

s aq

v s aq

398

12510mm 6mm

1.4725

51

112

221

93 102

227–228 1.446020 1.457020

⫺12

119–120 140

sl s aq; v s alc, bz, eth

33 48

0.06 aq; s alc, eth, dil HCl; sl s DMF v s aq v s aq

INTERACTIVE

d54 d55

Formula weight

ROTATED

d50 d51

1,4-Diaminobutane 4,4⬘-Diaminodiphenylamine sulfate trans-1,2-Diaminocyclohexane trans-1,4-Diaminocyclohexane trans-1,2-DiaminocyclohexaneN,N,N⬘,N⬘-tetraacetic acid hydrate 4,4⬘-Diaminodiphenylmethane 3,3⬘-Diaminodiphenyl sulfone 4,4⬘-Diaminodiphenyl sulfone 2,4-Diamino-6hydroxypyrimidine Diaminomaleonitrile 1,8-Diamino-p-menthane 3,3⬘-Diamino-Nmethyldipropylamine 2,4-Diamino-6-phenyl1,3,5-triazine 1,2-Diaminopropane 1,3-Diaminopropane

Formula

LEFT

d48

Name

d58 d59 d60 d61

d62 d63 d64 d65

1,3-Diamino-2propanol 2,6-Diaminopyridine 2,4-Diaminotoluene 3,4-Diaminotoluene 1,4-Diazabicyclo[2.2.2]octane 1,8-Diazabicyclo[5.4.0]undec-7-ene Diazomethane

H2NCH2CH(OH)CH2NH2

90.13

(H2N)2C5H3N (H2N)2C6H3CH3 (H2N)2C6H3CH3

109.13 122.17 122.17 112.18

40–45

235

221, 647 13, 124 13, 148 233, 484

120–122 97–99 91–93 158–160

283–285 15618mm 174

62

800.6mm

⬎110

152.24 CH2 "N"N

1-Diazo-2-naphthol-4sulfonic acid 1,2,5,6-Dibenzanthracene

1.018

1.521920

42.04

23, 25

⫺145

272.22

16, 595

160 dec

278.33

51, 369

266 subl

1.165

1,2-Diamino-4-nitrobenzene, n66 1,4-Diamino-2-nitrobenzene, n65 1,9-Diaminononane, n91 1,8-Diaminooctane, o24 1,5-Diaminopentane, p30 2,5-Diaminopentanoic acid, o51 1,2-Diaminopropane, p189 1,3-Diaminopropane, p190

1,4-Diaminobutane, b455 1,2-Diaminocyclohexane, c354 1,10-Diaminodecane, d9 2,2⬘-Diaminodiethylamine, d362 1,12-Diaminododecane, d804 1,2-Diaminoethane, e21 1,6-Diaminohexane, h53 1,3-Diamino-2-hydroxypropane, d56 Diaminonaphthalenes, n4, n5

⬎110

4, 290

s aq, alc

45 aq; 77 EtOH; 51 bz; 13 acet; 26 MeEtKe

⫺23

VERY EXPLOSIVE; s eth, dioxane

524

s bz, PE; sl s alc, eth

DEAN 37261 (McGHP)

d56

4,6-Diamino-4-pyrimidinol, d49 Diaminotoluenes, t167 thru t170 1,3-Diaminourea, c9 Diamylamine, d737 Diamyl ether, d738 Diamyl ketone, u11 Diazirine, d63 1,3-Diazole, i3

RIGHT ROTATED

d49

d51

d53

d61

d62

d64

d65

INTERACTIVE

No.

Name

d66 d67 d68

Dibenzofuran Dibenzothiophene Dibenzoylmethane

d69

d70

1.166

d71 d72 d73 d74

d85 d86

C6H5COCH2COC6H5

168.20 184.26 224.26

17, 70 17, 72 7, 769

Dibenzoyl peroxide

C6H5C("O)OOC("O)C6H5

242.23

(⫺)-Dibenzoyl-Ltartaric acid hydrate Dibenzylamine Dibenzyldisulfide Dibenzyl ether N,N⬘-Dibenzylethylenediamine Dibenzyl malonate Dibromoacetic acid Dibromoacetonitrile 2,4⬘-Dibromoacetophenone 1,4-Dibromobenzene 4,4⬘-Dibromobiphenyl 1,2-Dibromobutane 1,3-Dibromobutane 1,4-Dibromobutane meso-2,3-Dibromobutane 2,3-Dibromo-1,4butanediol 1,4-Dibromo-2,3butanediol trans-2,3-Dibromo-2butene-1,4-diol

[(C6H5COOCH(COOH)-]2 · H2O

Density, g/mL

Refractive index

1.088699 4

1.607999

Melting point,⬚C

Boiling point,⬚C

81–83 97–100 78–79

285 332–333 22018mm

9, 179

103–106

may explode when heated

376.34

9, 170

90–92

C6H5CH2NHCH2C6H5 C6H5CH2SSCH2C6H5 C6H5CH2OCH2C6H5 (C6H5CH2NHCH2-)2

197.28 246.39 198.27 240.35

12, 1035 6, 465 6, 434 12, 1067

CH2[CO2CH2C6H5]2 Br2CHCOOH Br2CHCN BrC6H4C("O)CH2Br

284.31 217.86 198.86 277.96

C6H4Br2 BrC6H4C6H4Br CH3CH2CH(Br)CH2Br CH3CH(Br)CH2CH2Br BrCH2CH2CH2CH2Br CH3CH(Br)CH(Br)CH3

⫺26 69 2 26

300 d ⬎ 270 298 1954mm

39–41

1880.2mm 13016mm 6924mm

1.026

1.573120

1.001420 4 1.02420 4

1.516820 1.562420

6, 436 2, 218 2, 219 7, 285

1.137

1.544720

235.92 312.00 215.93 215.93 215.93 215.93

5, 211 5, 580 1, 120 1, 120 1, 120 1.121

0.9641100

1.5743100

1.789 1.80020 1.808020 4 1.767

1.514120 1.508520 1.518620 1.510020

HOCH2CH(Br)CH(Br)CH2OH BrCH2C("O)C("O)CH2Br

247.93

13, 2176

88–90

243.89

1, 774

117–119

HOCH2C(Br)"C(Br)CH2OH

245.91

11, 260

112–114

2.296

1.539320

Flash point,⬚C

s alc, bz, eth; i aq s aq; v s alc, bz 4.4 alc; s eth, aq NaOH sl s aq, alc; s bz, chl, eth

143 135 (CC) ⬎110

⫺20

i aq; s alc, eth s hot alc, bz, eth misc alc, acet, chl, eth v s alc, bz, chl, eth

⬎110 ⬎110

108–110 87.3 167–170

Solubility in 100 parts solvent

v s warm alc; s eth 220 355–360 6020mm 175 198 7447mm 1501.5mm

1.4 alc; v s eth; s bz s bz; sl s hot alc ⬎110 110 ⬎110

s chl, eth s chl

INTERACTIVE

d87

Beilstein reference

ROTATED

d79 d80 d81 d82 d83 d84

Formula weight

LEFT

d75 d76 d77 d78

Formula

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

d89 d90 d91 d92 d93 d94 d95 d96 d97 d98

1.167

d99 d100 d101

Dibromochloromethane trans-1,2-Dibromocyclohexane 1,2-Dibromo-2-chloro1,1,2-trifluoroethane 1,10-Dibromodecane 1,2-Dibromo-1,1difluoroethane Dibromodifluoromethane 1,2-Dibromo-3,3-dimethylbutane 1,3-Dibromo-5,5-dimethylhydantoin 1,1-Dibromoethane 1,2-Dibromoethane (1,2-Dibromoethyl)benzene cis-1,2-Dibromoethylene trans-1,2-Dibromoethylene 1,2-Dibromoethyltrichlorosilane

208.29

1, 67

2,451

1.546520

C6H10Br2

241.96

5, 24

1.784

1.551520

FCCl(Br)C(Br)F2

276.5

Br(CH2)10Br CH2BrC(Br)F2

300.09 223.87

Br2CF2 (CH3)3CCH(Br)CH2Br

20

⫺22

20

120748mm

none

14610mm

⬎110

93–94

none

misc alc, bz, eth

2.2478

1.4275

11, 64 1, 92

1.33530 2.223820

1.491220 1.445620

27 ⫺61.3

16015mm 92.4

⬎110 none

sl s alc; s eth i aq

209.81

11, 16

2.28815 4

1.401620

⫺110

25

none

0.1 aq; misc alc, bz, chl, eth

243.98

1, 151

1.610

1.505320

733mm

83

10.0 70–74

113 131.7 14015mm

none none

i aq; v s alc, eth 0.43 aq; misc alc, eth

s alc, bz, chl, eth

185.93

197 dec

CH3CHBr2 BrCH2CH2Br C6H5CH(Br)CH2Br

187.86 187.86 263.97

1, 90 1, 90 5, 356

2.05520 4 2.180220 4

1.537920 1.538720

BrCH"CHBr

185.86

1, 190

2.2117 4

1.543118

⫺53

112.5

none

BrCH"CHBr

185.86

1, 190

2.246

1.550518

⫺6.5

108

none

BrCH2CH(Br)SiCl3

321.3

2.04620 4

1.53720

9011mm

Dibenzyl, d752

Dibenzyl ketone, d767

RIGHT

Dibenzo[b,e]pyridine, a60 Dibenzoyl, b35

HCClBr2

DEAN 37261 (McGHP)

d88

ROTATED

d66

d67

d95

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

d102

4⬘5⬘-Dibromofluorescein 1,4-Dibromo-2-fluorobenzene 2,4-Dibromo-1-fluorobenzene Dibromofluoromethane 1,2-Dibromohexafluoropropane 1,6-Dibromohexane 2,5-Dibromo-3,4hexanedione 5,7-Dibromo-8hydroxyquinoline 2,4-Dibromomesitylene Dibromomethane

d103 d104 d104a d105

1.168

d106 d107 d108 d109 d110

d112

d114 d115

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

490.12

19, 228

270–273

Br2C6H3F

253.91

54, 684

33–36

Br2C6H3F

253.91

Br2CHF

191.83

CF3CF(Br)C(Br)F2

309.84

14, 218

2.169

1.360520

Br(CH2)6Br CH3CHBrC("O)C("O)CH(Br)CH3

243.98 271.95

1, 145 13, 3132

1.58618 4 1.766

1.506620 1.512020

302.96

21, 97

1,3,5-(CH3)3-C6HBr2 CH2Br2

278.00 173.85

5, 408 1, 67

Br2C6H2(CH3)OH

265.94

6, 406

49–50

316.99

213, 1240

126–130

Br2C10H5OH

301.98

6, 652

105–107

Br2C6H2(NO2)NH2

295.93

12, 743

206–208

sl s aq; s HOAc

Br2C6H3NO2

280.91

5, 250

2.374

82–84

s bz, hot alc

Br(CH2)8Br CH3CH(Br)CH2CH2CH2Br Br(CH2)5Br Br2C6H3OH

272.03 229.95 229.95 251.92

1, 160 1, 131 1, 131 6, 202

1.477 1.687 1.687915 4

2.04720

2.495620 4

1.584020

1.541920

1.498120 1.508520 1.509220

s hot alc, HOAc 216

101

10522mm

92

⫺78

65

⫺95

72734mm

none

243 10310mm

⬎110 ⬎110

200–201

subl

61–63 ⫺52.7

278–279 96–97

15–16 ⫺34 ⫺34 40–42

misc eth

s alc, bz; v s eth

none

1.15 aq; misc alc, bz, acet, chl, eth

⬎110

272 9925mm 11015mm 15411mm

⬎110 ⬎110 ⬎110 ⬎110

INTERACTIVE

d116 d117 d118 d119

Beilstein reference

ROTATED

d113

2,6-Dibromo-4-methylphenol 5,7-Dibromo-2-methyl8-quinolinol 1,6-Dibromo-2naphthol 2,6-Dibromo-4-nitroaniline 2,5-Dibromonitrobenzene 1,8-Dibromooctane 1,4-Dibromopentane 1,5-Dibromopentane 2,4-Dibromophenol

Formula weight

LEFT

d111

Formula

1,2-Dibromopropane

CH3CH(Br)CH2Br

201.90

1, 109

1.93320

1.520320

⫺55.5

142

none

d121 d122

1,3-Dibromopropane 1,3-Dibromo-2propanol 2,3-Dibromo-1propanol 2,3-Dibromopropene 2,3-Dibromopropionic acid 2,3-Dibromopropionitrile 2,6-Dibromopyridine meso-2,3-Dibromosuccinic acid 1,2-Dibromotetrachloroethane 1,2-Dibromotetrafluoroethane 2,5-Dibromothiophene ␣,␣-Dibromotoluene 1,2-Dibromo-1,1,2trifluoroethane ␣,␣-Dibromo-o-xylene

BrCH2CH2CH2Br BrCH2CH(OH)CH2Br

201.90 217.90

1, 110 1, 365

1.971225 4 2.136

1.523320 1.551420

⫺36

166.8 837mm

54 46

BrCH2CH(Br)CH2OH

217.90

1, 357

2.12020 4

1.559920

9710mm

⬎110

BrCH2C(Br)"CH2 BrCH2CH(Br)COOH

199.88 231.88

1, 201 2, 258

1.933620 4

1.547020

140–143 16020mm

81

BrCH2CH(Br)CN

212.88

2, 259

2.140

BrC5H3N HOOCCH(Br)CH(Br)COOH BrCCl2CCl2Br

236.91 275.89

202, 153 2, 625

325.65

1, 93

BrCF2CF2Br

259.83

Br2C4H2S C6H5CHBr2 HC(Br)FC(Br)F2

241.94 249.94 241.8

C6H4(CH2Br)2

263.97

d123 d124 d125 d126 d127 d128 d129 d130

1.169

d131 d132 d133 d134

64–66 1.545020

sl s aq; misc alc, bz, acet, eth s aq, alc, bz

173 118–119 275 subl

2.713

0.2 aq; misc alc, bz, chl, eth 0.17 aq; s alc, eth

255 v s aq, alc

222 dec

none

2.14925

1.36725

⫺110.5

47

none

17, 33 5, 308 1, 92

2.14723 23 1.51015 2.27427

1.628920 1.614720 1.419124

⫺6

211 15623mm 76.5

99 ⬎110

5, 366

1.960

92–94

DEAN 37261 (McGHP)

d120

i aq; v s alc, eth i aq; misc alc, eth

sl s alc, chl, eth

5,7-Dibromo-8-quinolinol, d108

RIGHT ROTATED

d102

d108

d112

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued) Beilstein reference

Refractive index

22, 575 4, 157

1.0120 1.110 0.837420 20 0.962 0.767020

1.474020 1.413120 1.436020 1.417720

129.25 173.29

4, 162 43, 682

0.753 0.86020 20

1.410020 1.44420

C6H5N(C4H9)2

205.34

123, 95

0.90420

1.529720

C4H9O2C(CH2)8CO2C4H9 (CH3)3COC("O)OC(CH3)3

214.45 218.25

2, 719

0.936620 0.950

1.441520 1.410320

[(CH3)3C]2C6H2(OH)2

222.33

C4H9SSC4H9 (CH3)3CSSC(CH3)3 C4H9OC4H9 (CH3)2NCH2C6H2[C(CH3)3]2OH

178.36 178.36 130.22 263.43

12, 400

[CH3(CH2)3]2NCH2CH2NH2

172.32

44, 1182

HC("O)N(C4H9)2 [-CH2CH2CO2(CH2)3CH3]2 [(CH3)3C]2C6H2-1,4-(OH)2

157.26 258.36 222.33

22, 575 6, 3, 4741

C4H9O2CCH"CHCO2C4H9 CH2CO2C(CH3)3

228.29 216.27

23, 1925 23, 1621

Name

d135 d136 d137 d138 d139

␣,␣-Dibromo-p-xylene Dibutoxydibutyltin 1,2-Dibutoxyethane Dibutyl adipate Dibutylamine

C6H4(CH2Br)2 [CH3(CH2)3O]2Sn[(CH2)3CH3]2 C4H9OCH2CH2OC4H9 [-CH2CH2CO2(CH2)3CH3]2 (C4H9)2NH

263.97 379.15 174.28 258.36 129.25

5, 386

d140 d141

Di-sec-butylamine N,N-Dibutylaminoethanol N,N-Dibutylaniline

[C2H5CH(CH3)]2NH (C4H9)2NCH2CH2OH

d142

1.170

Density, g/mL

d143 d144 d145

d151 d152 d153 d154 d155

Flash point,⬚C

⫺62

261 1380.05mm 203.6 305 159.6

40 85 ⬎110 47

⬍ ⫺70

135 229–230

20 91

267–275

⬎110

344–345 560.5mm

178 37

231.2 229–233 140 17230mm

93 93 25

⫺69.1

⫺10 23

Solubility in 100 parts solvent v s alc, chl; s eth 0.2 aq; misc alc, acet 0.47 aq; s alc, acet, eth EtOAc, PE

i aq, MeOH; s acet, bz, EtOH, EtOAc, eth 0.004 aq

217–219

1, 369 134, 2014

⫺71

0.938320 4 0.935 0.768920 4

1.492020 1.4920 1.399220

0.823

1.443020

11724mm

87

0.864 0.962

1.442920 1.435820

12015mm 305

100 ⬎110

281 9310mm

141 88

⫺95 93–94

i aq; misc alc, eth 0.03 aq; misc alc, eth

217–219 0.995020

1.445420 1.418420

⬍ ⫺80 ⫺6.0

0.05 aq

INTERACTIVE

CO2C(CH3)3

72–74

Boiling point,⬚C

ROTATED

d150

Melting point,⬚C

LEFT

d146 d147 d148 d149

Dibutyl decanedioate Di-tert-butyl dicarbonate 2,5-Di-tert-butyl-1,4dihydroxybenzene Dibutyl disulfide Di-tert-butyl disulfide Dibutyl ether 2,6-Di-tert-butyl-4(dimethylaminomethyl)phenol N,N-Dibutylethylenediamine N,N-Dibutylformamide Dibutyl hexanedioate 2,5-Di-tert-butylhydroquinone Dibutyl maleate Di-tert-butyl malonate

Formula

Formula weight

No.

[(CH3)3C]2C6H2(CH3)OH

220.36

63, 2073

1.04820 4

1.485975

[-(CH2)3CO2(CH2)3CH3]2 C4H9O2CCO2C4H9 (CH3)3CO9OC(CH3)3 [(CH3)3C]2C6H3OH [CH3CH2CH(CH3)]2C6H3OH [(CH3)3C]2C6H3OH [(CH3)3C]2C6H3OH (C4H9O)2P(O)H C6H4 1,2-[CO2C4H9]2

286.41 202.25 146.23 206.33 206.23 206.23 206.23 194.21 278.35

23, 1767 2, 540 13, 1580

0.948 0.98620 20 0.79420

1.439020 1.423220 1.389020

0.918

1.510020

C4H9NH(CH2)3NHC4H9

186.34

d167

N,N-Dibutyl-1,3propanediamine Dibutyl suberate

286.41

d168 d169 d170 d171 d172 d173 d174 d175 d176 d177 d178

Dibutyl succinate Dibutyl sulfate Dibutyl sulfide Di-tert-butyl sulfide Dibutyl sulfite Dibutyl sulfone Dibutyl L-tartrate N,N-Dibutyl-2-thiourea Dibutyltin diacetate Dibutyltin dichloride Dibutyltin dilaurate

CH3(CH2)3O2C(CH2)6CO2(CH2)3CH3 [C4H9O2CCH2⫺]2 C4H9OSO2OC4H9 C4H9SC4H9 (CH3)3CSC(CH3)3 (C4H9O)2S("O) (C4H9)2SO2 [-CH(OH)CO2(CH2)3CH3]2 C4H9NC("S)NHC4H9 (CH3CO2)2Sn(C4H9)2 (C4H9)SnCl2 [CH3(CH2)10CO2]2Sn(C4H9)2

230.30 210.29 146.30 146.30 194.29 178.29 262.31 188.34 351.01 303.83 631.56

d157 d158 d159 d160 d161 d162 d163 d164 d165 d166

1.171

11, 187 92, 586

⫺30.0 ⫺40 56.5 ⫺42 35–38 87–89

265

127

1764.5mm 239–240 110 263.5 255–260 253

⬎110 108 1 115 127 118

11911mm 340

121 157

0.995 1.046520 4

1.423920 1.491120

0.827

1.446320

205

103

23, 1767

0.948

1.439020

175.54.5mm

⬎110

22, 551

0.976820 4 1.05925 4 0.838620 0.815 0.994422 4

1.429920 1.421320 1.453020 1.450620 1.431020

1.091

1.446520

1.320

1.470020

1.066

1.468320

1, 370 12, 397 1, 371 3, 518

Merck: 12, 3089

⫺29.0 ⫺80

46 22 63–65 39–41 22–24

274.5 13211mm 185 151 10815mm 295 1755mm

misc alc, ketones, PE misc acet, octane s hot alc; i alk s hot alc; i alk

0.01 aq; v s alc, bz, acet, eth

i aq; s alc, eth 76 48

i aq; v s alc, eth

143 ⬎110

i aq; s alc, eth i aq; s alc; sl s eth

14510mm 13510mm

⬎110 ⬎110 ⬎110

2,5-Di-tert-butylhydroquinone, d145 Dibutyl ketone, n101 Dibutyl sebacate, d143

s PE, bz, acet, eth, org esters

ROTATED

Dibutyl carbitol, b151 Dibutyl cellosolve, d137 Di-tert-butylcresol, d156

⫺35

s alc, bz, acet, PE

RIGHT

Dibutyl adipate, d152 Dibutyl 1,2-benzenedicarboxylate, d165 Dibutyl butanedioate, d168 N,N-Dibutyl-1-butanamine, t208

63, 2061

70

DEAN 37261 (McGHP)

2,6-Di-tert-butyl-4methylphenol Dibutyl octanedioate Dibutyl oxalate Di-tert-butyl peroxide 2,4-Di-tert-butylphenol 2,6-Di-sec-butylphenol 2,6-Di-tert-butylphenol 3,5-Di-tert-butylphenol Dibutyl phosphite Dibutyl 1,2-phthalate

d156

INTERACTIVE

Dibutyltin maleate Dibutyltin oxide Dicaprolactone 2(acryloxy)ethyl ester Dichloroacetic acid 1,1-Dichloroacetone 1,3-Dichloroacetone 2⬘,4⬘-Dichloroacetophenone Dichloroacetyl chloride 2,3-Dichloroaniline 2,4-Dichloroaniline 2,5-Dichloroaniline 2,6-Dichloroaniline 3,4-Dichloroaniline 3,5-Dichloroaniline 1,5-Dichloroanthraquinone 2,3-Dichlorobenzaldehyde 2,4-Dichlorobenzaldehyde 2,4-Dichlorobenzamide 2,6-Dichlorobenzamide 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene 2,5-Dichlorobenzenesulfonyl chloride 2,4-Dichlorobenzoic acid

d182 d183 d184 d185 d186

1.172

d187 d188 d189 d190 d191 d192 d193 d194 d195 d196 d197 d198 d199 d200 d201 d202

Formula weight

Beilstein reference

346.98 248.92 344.41

41, 588

Cl2CHCOOH CH3C("O)CHCl2 ClCH2C("O)CH2Cl Cl2C6H3C("O)CH3

128.94 126.97 126.97 189.04

Cl2CHC("O)Cl

(C4H9)2SnO HO(CH2)5CO2(CH2)5CO2CH2CH2O2CCH"CH2

Density, g/mL

Refractive index

Melting point,⬚C 135–140 ⬎ 300

1.100

1.466020

2, 202 1, 654 1, 655 7, 282

1.56320 4 1.30518 15 1.383

1.446220 1.445520

147.39

2, 204

1.531516 4

Cl2C6H3NH2 Cl2C6H3NH2 Cl2C6H3NH2 Cl2C6H3NH2 Cl2C6H3NH2 Cl2C6H3NH2

162.02 162.02 162.02 162.02 162.02 162.02 277.11

12, 621 12, 621 12, 625 12, 626 12, 626 12, 626 7, 787

Cl2C6H3CHO

175.01

73, 878

64–67

Cl2C6H3CHO

175.01

7, 236

69–73

Cl2C6H3CONH2 Cl2C6H3CONH2 C6H4Cl2 C6H4Cl2 C6H4Cl2 Cl2C6H3SO2Cl

190.03 190.03 147.00 147.00 147.00 245.51

93, 1376 91, 149 5, 201 5, 202 5, 203 111, 15

Cl2C6H3COOH

191.01

9, 342

Boiling point,⬚C

1.563520

1.596920

1.3059 1.2884 1.2417

39–41 33–34

1.460320

1.56720

20 4 20 4 6

9–11

20

1.5510 1.546020 1.528520

23–24 59–62 49–51 38–41 70–72 51–53 245–247

191–194 196–199 ⫺17.0 ⫺24.8 53 36–37 157–160

Flash point,⬚C

Solubility in 100 parts solvent

⬎110

193–194 120 173 14515mm

⬎110 24 89 ⬎110

misc aq, alc, eth s sl aq; s alc, eth

107–108

none

dec aq, alc; misc eth

252 245 251

⬎110

s alc; v s eth sl s aq; s alc, eth s alc, bz, eth

272 259741mm

⬎110 ⬎110 ⬎110

233

180.4 173.1 174.1

i aq

s alc, eth; sl s bz i aq; s alc, eth sl s alc, bz, acet

i aq; s alc

66 72 66 ⬎110

misc alc, bz, eth 0.01 aq; s alc, eth s alc, bz, chl, eth d hot alc, hot aq s hot aq, alc, bz, chl

INTERACTIVE

d179 d180 d181

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

d204 d205 d206 d207 d208 d209 d210 d211

1.173

d212 d213 d214 d215 d216 d217

2,5-Dichlorobenzoic acid 3,4-Dichlorobenzoic acid 4,4⬘-Dichlorobenzophenone 2,4-Dichlorobenzotrifluoride 3,4-Dichlorobenzotrifluoride 2,4-Dichlorobenzoyl chloride 3,4-Dichlorobenzoyl chloride 1,4-Dichlorobutane cis-1,4-Dichloro-2butene 3,4-Dichloro-1-butene 1,4-Dichloro-2-butyne Dichloro(2-chloroethyl)methylsilane Dichloro(3-chloropropyl)methylsilane 1,10-Dichlorodecane 1,1-Dichloro-2,2-diethoxyethane

Cl2C6H3COOH

191.01

9, 342

154–157

Cl2C6H3COOH

191.01

9, 343

207–209

(ClC6H4)2C"O

251.11

7, 420

144–146

Cl2C6H3CF3

215.00

53, 698

1.484

1.481020

Cl2C6H3CF3

215.00

53, 698

1.478

1.475020

Cl2C6H3C("O)Cl

209.46

9, 342

1.494

1.529720

Cl2C6H3C("O)Cl

209.46

9, 344

ClCH2CH2CH2CH2Cl ClCH2CH"CHCH2Cl

127.01 125.00

1, 119 13, 743

1.159820 4 1.18825 4

ClCH2CH(Cl)CH"CH2 ClCH2C#CCH2Cl ClCH2CH2SiCl2(CH3)

125.00 122.98 177.53

13, 725 13, 927 43, 1892

Cl(CH2)3Si(CH3)Cl2

191.56

Cl(CH2)10Cl Cl2CHCH(OC2H5)2

211.18 187.07

sl s aq; s alc, eth s hot aq, eth; v s alc

353

s hot alc, v s chl, eth

117–118

72

⫺12

173–174

65

16–18

15034mm

137

dec aq, alc

30–33

242

142

dec aq, alc

1.456620 1.488725

⫺38 ⫺48

161–163 152

40 55

i aq; s chl i aq; s org solvents

1.150 1.25820 4 1.261

1.465820 1.504820 1.458020

⫺61

123 165–168 157744mm

28 160 32

44, 4170

1.227

1.462020

8018mm

59

13, 522 1, 614

0.999 1.138

1.460520 1.436020

16828mm 183–184

⬎110 60

2,6-Dichlorobenzyl chloride, t253

15.6

2,2⬘-Dichlorodiethyl ether, b163

RIGHT

Dichloroacetaldehyde diethyl acetal, d217

301

DEAN 37261 (McGHP)

d203

ROTATED

d179

d193

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued) Beilstein reference

Density, g/mL

Refractive index

Name

d218

Cl2CF2

120.91

1, 61

1.486⫺30

(CH3)3CCH2CHCl2

155.07

13, 409

1.027

197.02

242, 158

(C6H5)2CCl2

237.13

5, 590

1.235

1.604020

d222 d223

Dichlorodifluoromethane 1,1-Dichloro-3,3dimethylbutane 1,3-Dichloro-3,5dimethylhydantoin Dichlorodiphenylmethane Dichlorodimethylsilane Dichlorodiphenylsilane

(CH3)2SiCl2 (C6H5)2SiCl2

129.06 253.20

1.06420 4 1.22220

1.403820

16, 910

d224 d225 d226

1,12-Dichlorododecane 1,1-Dichloroethane 1,2-Dichloroethane

Cl(CH2)12Cl CH3CHCl2 ClCH2CH2Cl

239.23 98.96 98.96

11, 67 1, 83 1, 84

1.175720 4 1.235120 4

d227

1,1-Dichloroethylene

H2C"CCl2

96.94

1, 186

d228

cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene 2,2⬘-Dichloroethyl ether 2,2-Dichloroethyl methyl ether Dichloroethylmethylsilane Dichlorofluoromethane 1,6-Dichlorohexane Dichloromethane Dichloromethane-d2

ClCH"CHCl

96.94

ClCH"CHCl

d219 d220 d221

1.174

d230

d232 d233

Flash point,⬚C

Solubility in 100 parts solvent

⫺158

⫺29.8

⫺56

148

36

305

⬎110

⫺16 308–309

70 157

1.416420 1.444820

28–30 ⫺97 ⫺35.7

17210mm 57.3 83.5

⫺16 dec aq, alc ⬎110 ⫺17 13

1.212920 4

1.424720

⫺122.6

31.6

⫺28

1, 188

1.283820 4

1.449020

⫺80.1

60

2

0.51 aq; misc alc 0.8 aq; misc alc, chl, eth 0.01 aq; s alc, bz, chl, eth 0.7 aq; s alc, eth

96.94

1, 188

1.256520

1.445220

⫺49.8

48.7

2

0.6 aq; s alc, eth

ClCH2CH2OCH2CH2Cl

143.01

12, 335

1.222020 20

1.45720

178.5

55

1.1 aq; s alc, bz, eth

Cl2CHCH2OCH3

128.99

1.226

1.437520

1.063

20

1.4190

1.438820

0.01 aq; 9 bz; 5.5 chl; 6 diox; s alc, eth

134–136

33

(C2H5)Si(CH3)Cl2

143.09

100

FCHCl2

102.92

1, 61

1.4059

1.37249

⫺135

8.9

Cl(CH2)6Cl CH2Cl2 CD2Cl2

155.07 84.93 86.95

1, 144 1, 60 14, 39

1.068 1.326520 1.3621

1.456820 1.424620 1.421820

⫺95

8715mm 40 40

43

73 none none

69 HOAc; 108 diox; s alc, eth; i aq s chl 1.3 aq; misc alc, eth

INTERACTIVE

d234 d235 d236

Boiling point,⬚C

ROTATED

d231

Melting point,⬚C

LEFT

d229

Formula

Formula weight

No.

d238 d239 d240 d241 d242 d243 d244 d245 d246

1.175

d247 d248 d249

␣,␣-Dichloromethyl methyl ether Dichloro(methyl)octylsilane Dichloro(methyl)phenylsilane Dichloro(methyl)silane Dichloro(methyl)vinylsilane 2,4-Dichloro-1naphthol 2,3-Dichloro-1,4naphthoquinone 2,6-Dichloro-4-nitroaniline 2,3-Dichloronitrobenzene 2,4-Dichloronitrobenzene 2,5-Dichloronitrobenzene 3,4-Dichloronitrobenzene 2,4-Dichloro-6nitrophenol

Cl2CHOCH3

114.96

CH3(CH2)7Si(CH3)Cl2

227.25

4, 4, 4182

1.271

1.430020

85

42

0.973

1.444020

946mm

98

1.176

20

1.5190

205

82

1.105 1.08720 4

1.39820 1.430020

41 92

⫺32 4

C6H5Si(CH3)Cl2

191.13

HSi(CH3)Cl2 H2C"CHSi(CH3)Cl2

115.04 141.07

41, 581

Cl2C10H5OH

213.06

6, 612

108

227.05

7, 729

190–192

Cl2C6H2(NO2)NH2

207.02

12, 735

190–192

Cl2C6H3NO2

192.00

5, 245

1.72114

61–62

257–258

123

s PE

Cl2C6H3NO2

192.00

5, 245

1.43980

29–32

258

⬎110

s hot alc; misc eth

Cl2C6H3NO2

192.00

5, 245

54–57

266–269

⬎110

Cl2C6H3NO2

192.00

5, 246

41–44

256

123

Cl2C6H2(NO2)OH

208.00

6, 241

sl s alc, bz, eth

118–120

4,4⬘-Dichloro-␣-methylbenzhydrol, b169 sym-Dichloromethyl ether, t165a

Dichloroisopropyl alcohol, d264 2,4-Dichloro-1-methylbenzene, d274 (Dichloromethyl)benzene, d273

RIGHT

5,5⬘-Dichloro-2,2⬘-dihydroxydiphenylmethane, m243 1,1-Dichlorodimethyl ether, d237 Dichlorohydrin, d264

1.45675

⫺93

DEAN 37261 (McGHP)

d237

ROTATED

d220

d243

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued) Refractive index

43, 1884

1.01120 4

1.40320

⫺62

222

141.04 163.00 163.00 163.00 163.00 221.04

1, 131 61, 102 6, 189 6, 189 6, 190

1.105820 4

1.455320

⫺72 58–60 42–43 56–58 65–68 136–140

6610mm 206 210 211 218–220 1600.4mm

Cl2C6H3O(CH2)3CO2H

249.10

63, 708

117–119

Cl2C6H3OCH(CH3)CO2H

235.07

6, 189

110–112

Cl2C6H3NCO

188.01

123, 1405

42–44

12018mm

⬎110

C6H5PCl2

178.99

16, 763

⫺51

222

⬎112

Cl2C6H2(CO2H)2

235.02

91, 366

CH3CH(Cl)CH2Cl

112.99

1, 105

1.155820

1.439020

⫺100

96

4

ClCH2CH2CH2Cl ClCH2CH(OH)CH2Cl

112.99 128.99

1, 105 1, 364

1.187820 4 1.198

1.448720 1.483520

⫺99.5 ⫺4

120–122 174.3

32 85

0.26 aq; misc alc, bz, chl, eth v s alc, eth 9.1 aq; misc alc, eth

ClCH2CH"CHCl ClCH2C(Cl)"CH2

110.97 110.97

1, 199 1, 199

1.21720 4 1.20425 25

1.47020 1.461120

97–112 94

25 10

i aq; s chl, eth misc alc; s eth

148.98 147.99 147.99 198.05 101.01

20, 231 20, 231 203, 3384

[Cl(CH3)2SiOSi(CH3)2-]2

351.53

Cl(CH2)5Cl Cl2C6H3OH Cl2C6H3OH Cl2C6H3OH Cl2C6H3OH Cl2C6H3OCH2COOH

1,3-Dichloropropane 1,3-Dichloro-2propanol 1,3-Dichloropropene 2,3-Dichloro-1propene 3,6-Dichloropyridazine 2,6-Dichloropyridine 3,5-Dichloropyridine 4,7-Dichloroquinoline Dichlorosilane

d257 d258 d259 d260 d261 d262 d263 d264 d265 d266 d267 d268 d269 d270 d270a

Cl2C5H3N Cl2C5H3N Cl2SiH2

1.319

1.598020

Boiling point,⬚C

Flash point,⬚C

26 113

i aq; s alc, eth s alc, eth v s alc, bz, chl, eth v s alc, bz, eth v s alc, eth s alc, bz, chl, eth 46 ppm aq25; s acet, alc, eth; sl s bz 350 ppm aq20; v s org solvents

201–203

66–69 86–88 65–67 84–86 ⫺122

Solubility in 100 parts solvent

s aq; v s eth

14810mm 8.3

INTERACTIVE

1,7-Dichlorooctamethyltetrasiloxane 1,5-Dichloropentane 2,3-Dichlorophenol 2,4-Dichlorophenol 2,5-Dichlorophenol 2,6-Dichlorophenol 2,4-Dichlorophenoxyacetic acid 4-(2,4-Dichlorophenoxy)butanoic acid 2-(2,4-Dichlorophenoxy)propanoic acid 3,4-Dichlorophenyl isocyanate Dichlorophenylphosphine 4,5-Dichloro-ophthalic acid 1,2-Dichloropropane

Melting point,⬚C

ROTATED

d250

Beilstein reference

LEFT

Name

d251 d252 d253 d254 d255 d256

1.176

Density, g/mL

Formula

Formula weight

No.

F3CCFCl2

170.92

d271

1,2-Dichloro-1,1,2,2tetrafluoroethane

ClCF2CF2Cl

170.93

13, 152

d272 d273 d274 d275 d276 d277 d278

2,5-Dichlorothiophene ␣,␣-Dichlorotoluene 2,4-Dichlorotoluene 2,6-Dichlorotoluene 3,4-Dichlorotoluene ␣,␣-Dichloro-o-xylene ␣,␣-Dichloro-p-xylene

Cl2(C4H2S) C6H5CHCl2 Cl2C6H3CH3 Cl2C6H3CH3 Cl2C6H3CH3 C6H4(CH2Cl)2 C6H4(CH2Cl)2

153.03 161.03 161.03 161.03 161.03 175.06 175.06

17, 33 5, 297 5, 295 5, 296 5, 296 5, 364 5, 384

d279

2,5-Dichloro-p-xylene

Cl2C6H2(CH3)2

175.06

5, 384

d280 d281 d282 d283 d284 d285 d286

Dicumyl peroxide Dicyandiamide 1,2-Dicyanobenzene 1,3-Dicyanobenzene 1,4-Dicyanobutane 1,6-Dicyanohexane 2,4-Dicyano-3-methylglutaramide 1,5-Dicyanopentane

[C6H5C(CH3)2]2O2 H2NC("NH)NHCN C6H4(CN)2 C6H4(CN)2 NC(CH2)4CN NC(CH2)6CN CH3CH[CH(CN)CONH2]2

270.37 84.08 128.13 128.13 108.14 136.20 194.19

3, 91 9, 815 9, 836 2, 653 2, 694 22, 704

NC(CH2)5CN

122.17

2, 671

d287

1,1-Dichloro-2-propanone, d184 ␣,o-Dichlorotoluene, c56

1.45525 satd pressure 1.47020 4 satd pressure 1.442 1.254 1.246020 20 1.254 25 1.25125

1.30920

⫺57

4

1.309220

⫺94

3.6

1.562120 1.550020 1.551120 1.550720 1.547220

⫺40.5 ⫺16/⫺17 ⫺13 ⫺15 55–57 99–101

162 205 200.5 196–203 209 239–241 254

71

222

1.40025 4

0.951 0.954

1.438020 1.443620

0.951

1.441020

␣,p-Dichlorotoluene, c70

39–41 208–211 139–141 158–160 1–3 ⫺3.5 159–160

s alc, eth

59 92 79 82 85 107

i aq; misc alc, eth v s alc, eth i aq i aq; s chl i aq 22.5 acet; 20 bz; 4.5 CCl4; 11 eth; 18 EtOAc 27 acet; 44 bz; 39 eth; 32 EtOAc; 5 MeOH

⬎110 2.3 aq; 1.3 alc; i bz v s bz, alc; s hot eth s alc, bz, chl, eth 295 18515mm

93 ⬎110

17614mm

⬎110

1,2-Dicyanoethane, b456

RIGHT

1,1-Dichlorotetrafluoroethane

DEAN 37261 (McGHP)

1.177

d270b

ROTATED

d267

d270

INTERACTIVE

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

d288

Dicyclohexyl

C6H11C6H11

166.31

5, 108

0.864

1.478220

3–4

227

92

d289 d290

(C6H11)2NH C6H11N"C"NC6H11

181.32 206.33

0.910

1.484220

⫺2 35–36

255.8 1246mm

96 110

C6H4-1,2-(CO2C6H11)2

330.43

12, 6 Merck: 12, 3146 9, 799

132.21 218.30

5, 495 63, 1942

0.93025 4 1.050

1.505025 1.508020

170 13713mm

26 ⬎110

110.16 514.86

0.977 0.915

1.467020

160–162

33, 556

39 ⬎110

d296

Dicyclohexylamine N,N⬘-Dicyclohexylcarbodiimide Dicyclohexyl ophthalate Dicyclopentadiene Dicyclopentenyl methacrylate Dicyclopropyl ketone Didodecyl 3,3⬘-thiodipropionate Dieldrin

380.92

173, 526

d297

Diethanolamine

HOCH2CH2NHCH2CH2OH

105.14

4, 283

1.088130 4

1.474730

d298

2,2-Diethoxyacetophenone 4,4-Diethoxybutylamine 2,2-Diethoxy-N,N-dimethylethylamine Diethoxydimethylsilane Diethoxydiphenylsilane 1,1-Diethoxyethane 1,2-Diethoxyethane 2,2-Diethoxyethanol 2,2-Diethoxyethylamine Diethoxymethane

C6H5C("O)CH(OC2H5)2

208.26

71, 361

1.034

H2N(CH2)3CH(OC2H5)2

161.25

4, 319

(C2H5O)2CHCH2N(CH3)2

161.25

4, 308

(C2H5O)2Si(CH3)2

148.28

(C2H5O)2Si(C6H5)2

272.42

CH3CH(OC2H5)2 C2H5OCH2CH2OC2H5 (C2H5O)2CHCH2OH (C2H5O)2CHCH2NH2

118.18 118.18 134.18 133.19

(C2H5O)2CH2

104.15

d291 d292 d293 d294 d295

1.178

d300

d302 d303 d304 d305 d306

⫺1

40–42 176–177 28.0

269

172

1.499520

13410mm

⬎110

0.933

1.427520

196

62

0.883

1.412920

170

45

0.84020 4

1.381120

114

11

162, 608

1.032920 4

1.526920

1392mm

⬎110

1, 603 1, 468 1, 818 4, 308

0.825420 4 0.842 24 0.8884 0.916

1.381920 1.392220 1.416020 1.4170

102.2 121.4 167 162–163

⫺21 27 67 45

0.839

1.373220

87–88

⫺5

⫺87

⫺100 ⫺74

s alc, eth

i aq; s common org solvents except PE 96 aq; 4 bz; 0.8 eth; misc MeOH, acet

5 aq; misc alc, eth 21 aq s alc, eth

INTERACTIVE

d307

64–66

ROTATED

d301

7 MeOH; misc bz, acet, eth misc alc, bz, chl, eth

LEFT

d299

(C3H5)2C"O S[CH2CH2CO2(CH2)11CH3]2

Solubility in 100 parts solvent

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

d317

3-(Diethoxymethylsilyl)propylamine 2,5-Diethoxynitrobenzene Diethoxymethylvinylsilane 1,1-Diethoxypropane 3,3-Diethoxy-1propene 2,2-Diethoxytriethylamine N,N-Diethylacetamide Diethyl 1,3-acetonedicarboxylate Diethyl 2-acetylglutarate Diethyl acetylsuccinate

d318 d319

Diethyl adipate Diethyl allylmalonate

d320

Diethylaluminum chloride Diethylaluminum ethoxide Diethylaluminum iodide

d309 d310 d311 d312 d313 d314 d315 d316

1.179

d321 d322

CH3Si(OC2H5)2(CH2)3NH2

191.35

4, 4, 4201

(C2H5O)2C6H5NO2

211.22

6, 857 4

0.916

1.426020 48–51

20 4

20

888mm

75

16913mm

⬎110

(C2H5O)2Si(CH3)CH"CH2

160.29

4 , 4183

0.858

1.400

133–134

17

CH3CH2CH(OC2H5)2 (C2H5O)2CHCH"CH2

132.20 130.19

1, 630 1, 727

0.823220 4 0.854

1.388420 1.400020

122.8 125

7 4

(C2H5O)2CHCH2N(C2H5)2

189.30

4, 309

0.850

1.418920

194–195

65

CH3C("O)N(C2H5)2 C2H5OOCCH2C("O)CH2CO2C2H5 C2H5O2CCH2CH2CH[C("O)CH3]CO2C2H5 C2H5O2CCH2CH[C("O)CH3]CO2C2H5 C2H5O2C(CH2)4CO2C2H5 C2H5O2CCH(CH2CH"CH2)CO2C2H5 (C2H5)2AlCl

115.18 202.21

4, 110 3, 791

0.925 1.113

1.440120 1.438520

182–186 250

70 86

230.26

3, 809

1.071

1.438620

15411mm

⬎110

216.23

3, 801

1.081

1.434620

18350mm

⬎110

202.25 200.23

2, 652 2, 776

1.009 1.015

1.427020 1.430420

⫺18

251 222–223

110 71

120.56

43, 1972

0.961

⫺50

12650mm

⫺18

(C2H5)2AlOC2H5

130.17

43, 1972

0.850

2.5–4.5

10910mm

⫺18

(C2H5)2AlI

212.01

42, 1024

1.609

1204mm

⫺18

Diethylacetic acid, e100

Diethyl 2-acetylpentanedioate, d316

RIGHT

Diethyl acetal, d303

v s alc, eth

DEAN 37261 (McGHP)

d308

ROTATED

d292

d293

d296

INTERACTIVE

d323 d324 d325

Diethylamine Diethylamine HCl 2-(Diethylamino)acetonitrile 4-(Diethylamino)benzaldehyde 2-Diethylaminoethanol 2-Diethylaminoethylchloride HCl 2-(Diethylamino)ethyl methacrylate 3-(Diethylamino)phenol 3-Diethylamino-1,2propanediol 1-Diethylamino-2propanol 3-Diethylamino-1propanol 3-Diethylaminopropylamine N,N-Diethylaniline 2,6-Diethylaniline Diethyl azelate Diethyl azodicarboxylate 5,5-Diethylbarbituric acid

d326 d327 d328 d329 d330

1.180

d331 d332 d333 d334 d335 d336 d337 d338 d339

Diethyl benzalmalonate 1,2-Diethylbenzene 1,3-Diethylbenzene 1,4-Diethylbenzene

Formula weight

Beilstein reference

Density, g/mL

Refractive index

0.707420 4 1.04821 4 0.866

1.386410

(C2H5)2NH (C2H5)2NH · HCl (C2H5)2NCH2CN

73.14 109.60 112.18

4, 95 4, 95 4, 350

(C2H5)2NC6H4CHO

177.25

142, 25

(C2H5)2NCH2CH2OH ClCH2CH2N(C2H5)2 · HCl

117.19 172.10

4, 282 42, 618

0.880025

1.438920

H2C"C(CH3)CO2CH2CH2N(C2H5)2 (C2H5)2NC6H4OH

185.27

43, 676

0.922

1.444020

165.24

13, 408

(C2H5)2NCH2CH(OH)CH2OH (C2H5)2NCH2CH(OH)CH3

147.22

4, 302

0.97320 20

1.460220

131.22

42, 737

0.889

1.425520

(C2H5)2NCH2CH2CH2OH

131.22

4, 288

0.884

(C2H5)2NCH2CH2CH2NH2

130.24

C6H5N(C2H5)2 (C2H5)2C6H3NH2 C2H5O2C(CH2)7CO2C2H5 C2H5O2CN"NCO2C2H5

149.24 149.24 244.33 174.16

12, 164

C6H5CH"C(CO2C2H5)2 C6H4(C2H5)2 C6H4(C2H5)2 C6H4(C2H5)2

Melting point,⬚C

Boiling point,⬚C

⫺50.0 227–230

55.5 320–330 170

⫺23

39–41

1747mm

⬎110

⫺70 108–210

163

48

8010mm

76

1.426020

65–69

Flash point,⬚C

Solubility in 100 parts solvent misc aq, alc s aq, alc, chl; i eth

53

17015mm

s aq, alc, bz, eth

s aq, alc, eth

233–235

107

s aq, alc, chl, eth

5913mm

33

s alc

1.4435

8315mm

65

0.826

1.441620

159

58

2, 709 3, 123

0.930225 4 0.906 0.973 1.106

1.539425 1.545220 1.435020 1.428020

216 243 17218mm 10613mm

97 123 ⬎110 ⬎110

184.19

242, 279

1.220

248.28 134.22 134.22 134.22

9, 5, 5, 5,

1.107 0.880 0.864020 4 0.862020 4

892 426 426 426

13.5

⫺38 3 ⫺16

188–192

1.536520 1.502020 1.495020 1.494020

⫺31 ⫺83.9 ⫺42.8

1 aq; sl s alc, eth

0.7 aq; 7 alc; 1.3 chl; 3.2 eth; s acet, HOAc 21530mm 184 181.1 183.8

⬎110 49 50 56

s alc, eth s alc, eth

INTERACTIVE

d340 d340a d341 d342

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

d344 d345 d346 d347 d348 d349 d350 d351 d352

1.181

d353 d354 d355 d356

Diethyl benzylmalonate Diethyl benzophosphonate Diethyl bis(hydroxymethyl)malonate Diethyl bromomalonate Diethyl butylmalonate Diethylcarbamoyl chloride Diethyl carbonate

C6H5CH2CH(CO2C2H5)2

250.29

9, 869

1.064

1.486820

16210mm

⬎110

C6H5CH2P(O)(OC2H5)2

228.23

12, 164

1.095

1.497020

1081mm

⬎110

(HOCH2)2C(CO2C2H5)2

220.22

BrCH(CO2C2H5)2

239.07

2, 594

1.402225 4

1.455020

⫺54

235 dec

⬎110

i aq; misc alc, eth

C4H9CH(CO2C2H5)2 (C2H5)2N(O)Cl

216.28 135.59

21, 282 4, 120

0.983 1.070

1.4220 1.451520

⫺32

235–240 187–190

93 75

v s alc, eth d hot aq, hot alc

(C2H5O)2C"O

118.13

3, 5

0.976420 4

1.384320

⫺43.0

126

25

69 aq; misc alc, bz, eth, esters

Diethyl chlorophosphate Diethyl chlorothiophosphate Diethyl cyanophosphate N,N-Diethylcyclohexylamine Diethyl diethylmalonate 1,3-Diethyl-1,3diphenylurea Diethyl disulfide

(C2H5O)2P(O)Cl

172.55

1, 332

1.194

1.416520

602mm

61

(C2H5O)2P(S)Cl

188.61

13, 1332

1.200

1.471520

453mm

⬎110

(C2H5O)2P(O)CN

163.11

1.075

1.401220

10519mm

80

C6H11N(C2H5)2

155.29

12, 6

0.850

1.456220

194–195

57

(C2H5)2C(CO2C2H5)2

216.28

2, 686

0.990

1.423020

228–230

94

[C6H5N(C2H5)]2C"O

268.36

12, 422

C2H5SSC2H5

122.25

1, 347

154.0

40

73–75 0.99820 4

Diethyl cis-2-butanedioate, d377

1.506320

⫺101.5

Diethyl carbitol, b186

sl s aq; misc alc, eth

RIGHT

Diethylaminoacetaldehyde diethyl acetal, d313 3-Diethylaminopropylamine, d400

⬎110

49–51

DEAN 37261 (McGHP)

d343

ROTATED

d339

INTERACTIVE

Name

d357

Diethyldithiocarbamic acid, sodium salt Diethyl dithiophosphate N,N-Diethyldodecanamide Diethyl dodecanedioate Diethylene glycol Diethylenetriamine Diethylenetriaminepentaacetic acid N,N-Diethylethanolamine Diethyl ether Diethyl ethoxymethylenemalonate N,N-Diethylethylenediamine Diethyl ethylmalonate N,N-Diethylformamide Diethyl fumarate Diethyl glutarate

d358 d359 d360 d361 d362 d363 d364

1.182

d365 d366 d367 d368 d369 d370 d371

d373 d374 d375 d376

Beilstein reference

(C2H5)2NC("S)S⫺ Na⫹ · 3H2O

225.31

42, 613

(C2H5O)2P(S)SH

186.23

1, 333

CH3(CH2)10C("O)N(C2H5)2

255.45

C2H5O2C(CH2)10CO2C2H5

186.41

(HOCH2CH2)2O (H2NCH2CH2)NH [(HO2CCH2)2NCH2CH2]2N(CH2CO2H)N(CH2CO2H)2 HOCH2CH2N(C2H5)2

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

95–99 1.111

1.512020

601mm

82

0.847

1.454520

1662mm

⬎110

22, 616

0.951

1.440220

15

19314mm

⬎110

106.12 103.17 393.35

1, 468 4, 255 44, 2454

1.119715 0.954220 20

1.446020 1.482620

⫺10 ⫺35/⫺39 219–220

246 207

124 98

117.19

4, 282

0.884

1.441020

161

48

C2H5OC2H5 (C2H5O2C)2C"CHOC2H5

74.12 216.23

1, 314 3, 469

0.713420 4 1.070

1.352720 1.462020

34.6 279–281

⫺45 155

(C2H5)2NCH2CH2NH2

116.21

4, 251

0.827

1.436020

145–147

30

C2H5CH(CO2C2H5)2 (C2H5)2NCHO C2H5O2CCH"CHCO2C2H5 C2H5O2CCH2CH2CH2CO2C2H5 H2C"CHCH2CH(C2H5)CH"C(C2H5)CHO C2H5O2C(CH2)5CO2C2H5 C6H4[CO2CH2CH(C2H5)C4H9]2 (C2H5O)2P(O)H

188.22 101.15 172.18 188.22

2, 644 4, 109 2, 742 2, 633

1.00420 20 0.908 1.05220 4 1.022

1.415820 1.434020 1.440620 1.424020

775mm 176–177 218–219 237

88 60 91 96

0.862

1.467620

9112mm

86

192100mm 384

⬎110 207

i aq; s alc, eth

512mm

90

hyd aq; s alc, eth

(C2H5)2NOH C2H5O2CCH"CHCO2C2H5

166.27

⫺116.3

1–2 ⫺23.8

⫺24 ⫺50

216.28 390.56

2, 671 10, 1248

0.994520 0.98125 25

1.428020 1.485320

138.10

1, 330

1.07920 4

1.407620

89.14

4, 536

1.867

1.419520

⫺25

125–130

45

172.18

2, 751

1.068720

1.440020

⫺8.8

225.3

93

misc aq, alc, bz, eth

6 aq; misc alc, bz, chl

sl s aq; v s alc, eth misc aq; v s alc, eth 0.9 aq; v s alc; s eth

1.4 aq; s alc, eth

INTERACTIVE

d377

2,4-Diethyl-2,6heptadienal Diethyl heptanedioate Di-(2-ethylhexyl)-ophthalate Diethyl hydrogen phosphonate N,N-Diethylhydroxylamine Diethyl maleate

Formula weight

ROTATED

d372

Formula

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

C2H5O2CCH2CO2C2H5 HO2CC(C2H5)2CO2H (C2H5)2NH3

d384 d385

Diethyl malonate Diethylmalonic acid N,N-Diethylmethylamine Diethyl methylmalonate Diethyl 2-methyl-2⬘oxosuccinate N,N-Diethyl-4-nitrosoaniline Diethyl octanedioate Diethyl oxalate

d386 d386a d387

d381 d382 d383

1.183

d388 d389 d390 d391 d392 d393

160.17 160.17 87.17

2, 573 2, 686 4, 99

1.0550

1.413620

0.720

1.388720

20 4

⫺49.9 127

20

199.3 170–180 63–65

93 ⫺23

2.7 aq; misc alc, eth v s aq, alc, eth

C2H5O2CCH(CH3)CO2C2H5

174.20

2, 629

1.018

1.4130

198

76

C2H5O2CCH(CH3)C("O)CO2C2H5 C6H4(NO)N(C2H5)2

202.21

3, 794

1.073

1.431320

13823mm

⬎110

178.24

12, 684

C2H5O2C(CH2)6CO2C2H5 C2H5O2CCO2C2H5

230.30 146.14

2, 693 2, 535

0.982220 4 1.078520 4

1.432320 1.410220

282 185.4

⬎112 76

Diethyl oxydiformate

[C2H5OC("O)]2O

162.14

Merck: 12, 8182

1.1220 4

1.398020

9318mm

69

3,3-diethylpentane N1,N1-Diethyl-1,4pentanediamine N1,N1-Diethyl-1,4phenylenediamine Diethyl phenylmalonate Diethyl phosphite Diethyl o-phthalate N,N-Diethyl-1,3propanediamine 2,2-Diethyl-1,3propanediol

C(C2H5)4 CH3CH(NH2)(CH2)3N(C2H5)2

128.26 158.29

0.753620 0.817

1.420620 1.442920

146 200

68

(C2H5)2NC6H4NH2

164.25

Merck: 12, 6819 13, 75

0.988

1.571020

1165mm

⬎110

C6H5CH(CO2C2H5)2

236.27

9, 854

1.095020 4

1.491320

16

17014mm

⬎110

i aq; s alc

(C2H5)2P(O)H C6H4(CO2C2H5)2 (C2H5)2NCH2CH2CH2NH2

138.10 222.24 130.24

1, 330 9, 798

1.07920 4 1.23214 4 0.826

1.407920 1.504914 1.441620

⫺40

512mm 295 159

90 160 58

hyd aq; s alc, eth i aq; misc alc, eth

(C2H5)2C(CH2OH)2

132.20

1.05220

1.457425

61.3

12510mm

⫺33

i aq; s alc, eth 3.6 aq (gradual dec); misc alc, eth 50 alc; s esters, ketones; s aq s aq, alc, eth

25 aq; v s alc, eth

O,O-Diethyl O-p-nitrophenyl phosphorothioate, p3 Diethyl 3-oxoglutarate, d315 2,3-Diethylpentane, e210a Diethyl 2-pentenedioate, d371 Diethyl phosphorochloridate, d350 Diethyl phosphorochloridothionate, d351 Diethyl pimelate, d373 Diethyl propanedioate, d378

ROTATED

Diethylene glycol monomethyl ether, m73 Diethyleneimide oxide, m463 N,N-Diethylethanamine, t274 Diethyl ethanedioate, d385 N,N-Diethylethanolamine, d327 Diethyl ethoxycarbonylmethylphosphonate, t287 Di-2-ethylhexyl phthalate, b193 Diethyl ketone, p43

5.9 ⫺40.6

RIGHT

Diethylene dioxide, d733 Diethylene glycol, b198 Diethylene glycolamine, a164 Diethylene glycol dibutyl ether, b151 Diethylene glycol diethyl ether, b186 Diethylene glycol dimethyl ether, b214 Diethylene glycol monobutyl ether, b495 Diethylene glycol monoethyl ether, e41 Diethylene glycol monoethyl ether acetate, e41a

82–84

DEAN 37261 (McGHP)

d378 d379 d380

INTERACTIVE

Diethyl propylmalonate Diethyl sebacate Diethyl succinate Diethyl sulfate Diethyl sulfide Diethyl sulfite (⫹)-Diethyl-L-tartrate (⫺)-Diethyl-D-tartrate N,N-Diethyl-mtoluamide N,N-Diethyl-mtoluidine N,N-Diethyl-1,1,1-trimethylsilylamine Diethylzinc 1,2-Difluorobenzene 1,4-Difluorobenzene 1,1-Difluoroethane 1,1-Difluoroethylene Difluoromethane 2,4-Difluoronitrobenzene 1,1-Difluorotetrachloroethane 1,2-Difluorotetrachloroethane Dihexylamine Dihexyl ether 9,10-Dihydroanthracene (⫹)-Dihydrocarvone Dihydrocoumarin

d395 d396 d397 d398 d399 d400 d401 d402 d403

1.184

d404 d405 d406 d406a d407 d408 d409 d410 d411 d412 d413 d414 d415 d416 d417

Formula weight

Beilstein reference

Density, g/mL

Refractive index

C2H5O2CCH(C3H7)CO2C2H5

202.25

2, 657

0.987

1.418520

C2H5O2C(CH2)8CO2C2H5 C2H5O2C(CH2)2CO2C2H5 (C2H5O)2SO2 (C2H5)2S (C2H5O)2SO [-CH(OH)CO2C2H5]2 [-CH(OH)CO2C2H5]2 CH3C6H4C("O)N(C2H5)2

258.36 174.20 154.18 90.19 138.19 206.19 206.19 191.27

2, 717 2, 609 1, 327 1, 344 1, 325 3, 512 31, 181 92, 325

0.963 1.04020 4 1.17225 4 0.836720 4 1.883 1.20520 4 1.205 0.99620 4

1.436020 1.420020 1.400420 1.443020 1.45020 1.446020 1.446020 1.521220

CH3C6H4CN(C2H5)2

163.26

12, 857

0.922

(C2H5)2NSi(CH3)3

145.32

43, 1861

(C2H5)2Zn C6H4F2 C6H4F2 CH3CHF2 CH2 "CF2 CH2F2 F2C6H3NO2

123.49 114.09 114.09 66.05 64.04 52.02 159.09

ClF2CCCl3

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

221–222

91

312 217.7 208 92.1 158 280 16219mm 1111mm

⬎110 100 78 ⫺9 53 93 93 ⬎110

1.536020

231–232

100

0.767

1.411020

125–126

10

6, 672 52, 147 5, 199 13, 130 1, 186 1, 59 51, 129

1.206520 4 1.158 1.170120 0.90921

1.498320 1.443020 1.441020 1.3011⫺72

1.511020

118 92 89 ⫺24.7 ⫺86 ⫺51.6 203–204

⫺23 2 2

2.126 g/L 1.451

⫺28 ⫺34 ⫺13 ⫺117 ⫺144 ⫺136 9–10

203.83

1, 86

1.649

1.413

41

91

none

FCl2CCCl2F

203.83

13, 365

1.644725 4

1.41325

23.8

203.8

(C6H13)2NH (C6H13)2O

185.36 186.34 180.25

41, 384 13, 1656 5, 641

0.795 0.793620 4 0.880

1.432020 1.420420

95 77

108–110

192–195 226.2 312

152.24 148.16

73, 337 17, 315

0.92919 1.16918

1.471820 1.556320

25

221–222 272

81 ⬎110

1–2 ⫺21 ⫺25 ⫺103.9 17

Solubility in 100 parts solvent

0.14 aq; misc alc, eth i aq; misc alc, eth i aq; misc alc, eth i aq; misc alc, eth s aq(dec), alc sl s aq; misc alc, eth sl s aq; misc alc, eth i aq; v s alc, bz, eth

0.32 aq FLAMMABLE GAS 90 sl s alc; v s eth i aq; s alc, eth s alc, eth i aq; s ethers i aq; s alc, bz, eth

sl s alc, eth; s chl

INTERACTIVE

d394

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

d419

d420 d421 d422 d423 d424 d425

2,5-Dihydro-2,5-dimethoxyfurfurylamine 2,3-Dihydro-2,2-dimethyl-7-benzofuranol 3,4-Dihydro-2-ethoxy2H-pyran 2,3-Dihydrofuran 3,4-Dihydro-2methoxy-2H-pyran 3,4-Dihydro-1(2H)naphthalenone 3,4-Dihydro-2H-pyran 2⬘,4⬘-Dihydroacetophenone

159.19

183, 7426

1.102

1.460020

164.21

175, 4, 47

1.101

1.541020

0.957

1.439420

4216mm

24

54–55

⫺24 16

128.17

(HO)2C6H3C("O)CH3

1.185

Diethyl pyrocarbonate, d386 Diethyl suberate, d384 Diglycine, i7

9612mm

96

110

70.09 114.14

173, 141

0.927

1.423920 1.442520

146.19

7, 370

1.099

1.568520

5–6

1166mm

⬎110

84.12 152.15

0.92219 15 1.180

1.441020

⫺70 145–147

86

⫺15

8, 266

Diglycol, b198 Diglycolic acid, o67 Diglyme, b214

DEAN 37261 (McGHP)

d418

s aq, alc s warm alc, HOAc, pyr; i bz, eth

Dihexyl ketone, t264 1,2-Dihydroacenaphthylene, a2 2,5-Dihydroanisole, m67

RIGHT

d415

d416

d417

d418

ROTATED

d419

d420

d421

d422

d424

INTERACTIVE

d423

No.

Name

d426

d428

1,8-Dihydroxyanthraquinone 2,4-Dihydroxybenzaldehyde 1,2-Dihydroxybenzene

d429 d430 d431

d427

d432

1.186

d433 d434 d435

d439 d440 d441

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

240.21

8, 458

193–197

subl

(HO)2C6H3CHO

138.12

8, 241

135–136

22622mm

C6H4(OH)2

110.11

6, 759

1.3444

104–106

245.5

137

1,3-Dihydroxybenzene

C6H4(OH)2

110.11

62, 802

1.27215

109–110

276

171

1,4-Dihydroxybenzene 2,4-Dihydroxybenzoic acid 2,5-Dihydroxybenzoic acid 3,4-Dihydroxybenzoic acid 3,5-Dihydroxybenzoic acid 2,4-Dihydroxybenzophenone 2,2⬘-Dihydroxybiphenyl 4,6-Dihydroxy-2mercaptopyrimidine

C6H4(OH)2 (HO)2C6H3CO2H

110.11 154.12

6, 836 10, 377

1.33215

285–287

(HO)2C6H3CO2H

154.12

10, 384

170–171 213 rapid heating 199–200

(HO)2C6H3CO2H

154.12

10, 389

(HO)2C6H3CO2H

154.12

(HO)2C6H3C("O)C6H5

1,2-Dihydroxy-4methylbenzene 1,5-Dihydroxynaphthalene 1,6-Dihydroxynaphthalene 2,3-Dihydroxynaphthalene 2,7-Dihydroxynaphthalene

1.54

Solubility in 100 parts solvent 0.005 alc; 0.2 eth; s chl v s aq, alc, chl, eth 43 aq; s alc, bz, chl, eth; v s pyr, alkalis 110 aq; 110 alc; v s eth, glyc; sl s chl 7 aq; v s alc, eth s hot aq, alc, eth 0.5 aq; s alc, eth

200–202

2 aq; s alc, eth

10, 404

236 dec

sl s aq; s alc, eth

214.22

8, 312

144–145

v s alc, eth, HOAc

HOC6H4C6H4OH

186.21 144.15

6, 989 24, 476

110 236

315

s alc, bz, eth; sl s aq

(HO)2C6H3CH3

124.14

6, 878

67–69

251

v s aq, alc, eth

C10H6(OH)2

160.17

6, 980

259 dec

sl s aq; s alc; v s eth

C10H6(OH)2

160.17

6, 981

138–140

v s alc, eth

C10H6(OH)2

160.17

6, 982

162–164

v s alc, eth

C10H6(OH)2

160.17

6, 985

187 dec

sl s aq; v s alc, eth

1.12974 4

1.542574

INTERACTIVE

d442

Beilstein reference

ROTATED

d438

Formula weight

LEFT

d436 d437

Formula

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

(HO)2C10H5CO2H

204.19

10, 442

220 dec

(HO)2C10H5CO2H

204.19

10, 444

277 dec

90.08

1, 846

65–71

v s aq, alc, acet, eth

158

33 aq; 2 alc; 1 chl sl s ahot alc; s hot aq

d448 d449 d450 d451 d452

1,4-Dihydroxy-2naphthoic acid 3,5-Dihydroxy-2naphthoic acid 1,3-Dihydroxy-2propanone 7-(2,3-Dihydroxypropyl)theophylline 3,6-Dihydroxypyridazine 2,3-Dihydroxypyridine 1,4-Diiodobenzene 1,4-Diiodobutane 1,2-Diiodoethane Diiodomethane

d453 d454

1,5-Diiodopentane 1,3-Diiodopropane

d444 d445 d446 d447

HOCH2C("O)CH2OH

254.25 112.09

24, 312

306–308

(HO)2C5H3N C6H4I2 I(CH2)4I ICH2CH2I CH2I2

111.10 329.91 309.92 281.86 267.84

212, 107 5, 227 1, 123 1, 99 1, 71

2.350 2.13210 3.32520 4

1.742520

245 dec 131–133 6 81–84 6

285 15226mm 200 181

I(CH2)5I I(CH2)3I

323.94 295.88

1, 133 1, 115

2.177 2.575520 4

1.600220 1.642320

⫺13

1023mm 222

1.187

10,11-Dihydro-5H-dibenz[b,f]azepine, i9 2,5-Dihydro-2,5-dimethoxyfuran, d501 3,7-Dihydro-3,7-dimethyl-1H-pyridine-2,6-dione, t134 Dihydro-2(3H)-furanone, b617 2,3-Dihydroindene, i10 Dihydromyrcenol, m313 Dihydroresorcinol, c323

1.621220

3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione, c1 1,3-Dihydroxyacetone, d445 1,4-Dihydroxybenzene, h86 1,4-Dihydroxycyclohexane, c359 2,2⬘-Dihydroxydiethylamine, d297 N,N-Di(hydroxyethyl)aminoacetic acid, b199

sl s alc; v s eth

DEAN 37261 (McGHP)

d443

none ⬎110 ⬎110 ⬎110

sl s aq; s alc, eth 0.12 aq; misc alc, bz, eth, PE i aq; s chl, eth

2,2-Dihydroxy-1,3-indandione, i13 2,2-Dihydroxymethyl-1-butanol, e183 1,1-Di(hydroxymethyl)ethylamine, a215 Dihydroxypropane, p191, p192 3,5-Diiodosalicylic acid, h113 Diisobutyl adipate, d459

RIGHT ROTATED

d426

d437

d446

d447

INTERACTIVE

Diisobutylaluminum chloride Diisobutylaluminum hydride Diisobutylamine Diisobutyl ether Diisobutyl hexanedioate Diisobutyl o-phthalate 1,6-Diisocyanatohexane Diisodecyl phenyl phosphite Diisoheptyl o-phthalate Diisononyl o-phthalate Diisooctyl nonanedioate Diisooctyl o-phthalate Diisopentyl ether 1,3-Diisopropenylbenzene Diisopropylamine 2-(Diisopropylamino)ethanol 3-Diisopropylamino1,2-propanediol 2,6-Diisopropylaniline Diisopropyl azodicarboxylate 1,3-Diisopropylbenzene 1,4-Diisopropylbenzene Diisopropylcyanamide

d456 d457 d458 d459 d460 d461 d462

1.188

d463 d464 d465 d466 d466a d467 d468 d469 d470 d471 d472 d473 d474 d475

Formula weight

Beilstein reference

Density, g/mL

Refractive index 1.450620

Melting point,⬚C ⫺40

Boiling point,⬚C

Flash point,⬚C

15210mm

⫺18

1181mm

⫺18

137–139 122–124

29 8 160

Solubility in 100 parts solvent

[(CH3)2CHCH2]2AlCl

176.67

44, 4403

0.905

[(CH3)2CHCH2]2AlH

142.22

44, 4400

0.798

[(CH3)2CHCH2]2NH [(CH3)2CHCH2]2O [(CH3)2CHCH2O2CCH2CH2⫺]2

129.25 130.22 258.36

4, 166

0.740 0.76115 0.95025 25

1.408120

C6H4[CO2CH2CH(CH3)2]2 OCN(CH2)6NCO

278.35 168.20

92, 587 42, 711

1.03825 25 1.040

1.490020 1.452520

255

(C10H21O)2P(O)C6H5

438.64

0.940

1.480020

1765mm

C6H4(CO2C7H15)2 C6H4(CO2C9H19)2 C8H17O2C(CH2)7CO2C8H17

412.66

0.990 0.972 0.905

1.486020 1.485020 1.451010

2102mm

C6H4(CO2C8H17)2 [(CH3)2CHCH2CH2]2O C6H4[C(CH3)"CH2]2

390.56 158.28 158.25

0.983 0.777720 0.925

1.486020 1.408520 1.557120

172.5 231

91

[(CH3)2CH]2NH [(CH3)2CH]2NCH2CH2OH

101.19 145.25

0.715320 0.826

1.392420 1.441720

83.5 187–192

⫺1 57

[(CH3)2CH]2NCH2CH(OH)CH2OH [(CH3)2CH]2C6H3NH2 (CH3)2CHO2CNCO2CH(CH3)2 C6H4[CH(CH3)2]2

175.27

0.962

1.458320

13110mm

⬎110

177.29 202.21

12, 168

0.940 1.027

1.533220 1.420020

⫺45

257 750.25mm

123 106

162.28

5, 447

0.85620 4

1.489020

⫺63

203

76

misc alc, bz, eth, acet

C6H4[CH(CH3)2]2

162.28

52, 339

0.85720 4

1.488920

⫺17

204

76

misc alc, bz, acet, eth

[(CH3)2CH]2NCN

126.20

43, 279

0.839

1.427020

9325mm

78

4, 154 41, 430

⫺77

s alc, acet, eth, chl i aq; misc alc, eth

174 140

⬎110 ⬎110 ⬎110 ⬎110

⫺61

11 aq; s alc

INTERACTIVE

d455

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Diisopropyl ether

[(CH3)2CH]2O

102.17

1, 362

0.725820 4

1.367920

⫺86.9

68.4

⫺28

d477

N,N-Diisopropylethylamine Diisopropyl malonate

[(CH3)2CH]2NC2H5

129.25

4, 4, 511

0.742

1.413320

⬍ ⫺50

127

10

20

d478 d479 d480 d481 d482 d483 d484 d485 d486

1.189

d487 d488 d489 d490 d491 d492

188.22

2 , 1620

0.991

1.4120

178.28 166.16 234.25

61, 272 1, 363 3, 517

0.962 0.997 1.114

1.514020 1.407020 1.438720

(CH3)2CHNHCSNHCH(CH3)2

160.28

4, 155

84.07 154.25

173, 4297

HSCH2CH(OH)CH(OH)CH2SH HSCH2CH(SH)CH2OH

18

95

88

256 72–7520 15212mm

110 ⬎110 109

127

34

143–145 1.090

1.433020 42.43

1.238525 4

124.22

1.527025

v s aq, alc, chl, eth 12015mm

⬎110

8 aq(dec); s alc, eth

⬎110

sl s aq, alc, eth

⬎110

s alc, bz, eth s aq, alc s hot eth

150.24

27, 677

162 dec

(CH3O)2C6H3COCH3

180.20

82, 298

49–51

286–288

(CH3O)2C6H3NH2 (CH3O)2C6H3NH2 (CH3O)2C6H3NH2 (CH3O)2C6H3CHO

153.18 153.18 153.18 166.18

13, 784 13, 788 13, 780 8, 245

34–37 80–82 88 49–52

270 17622mm 14610mm

⬎110

(CH3O)2C6H3CHO

166.18

8, 255

42–43

281

⬎110

v s alc, eth

C6H4(OCH3)2

138.17

6, 771

22.5

206.3

87

sl s aq; s alc, eth

1.075

1.081925

1.523225

Diisopropyl ketone, d658

Dimedone, d596

ROTATED

Diisobutylene, t384 Diisobutyl ketone, d616

(CH3)2CHO2CCH2CO2CH(CH3)2 [(CH3)2CH]2C6H3OH [(CH3)2CHO]2P(O)H [-CH(OH)CO2CH(CH3)2]2

12mm

RIGHT

d493

2,6-Diisopropylphenol Diisopropyl phosphite (⫹)-Diisopropyl L-tartrate 1,3-Diisopropyl-2thiourea Diketene threo-1,4-Dimercapto2,3-butanediol 2,3-Dimercapto-1propanol 2,5-Dimercapto-1,3,4thiadiazole 3⬘4⬘-Dimethoxyacetophenone 2,4-Dimethoxyaniline 2,5-Dimethoxyaniline 3,4-Dimethoxyaniline 2,5-Dimethoxybenzaldehyde 3,4-Dimethoxybenzaldehyde 1,2-Dimethoxybenzene

3

1.2 aq; misc alc, bz, chl, eth

DEAN 37261 (McGHP)

d476

d483

d486

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

1,3-Dimethoxybenzene 1,4-Dimethoxybenzene 3,4-Dimethoxybenzoic acid 3,5-Dimethoxybenzoic acid 2,6-Dimethoxybenzoyl chloride 3,4-Dimethoxybenzyl alcohol 2,2-Dimethoxycyclohexanol 2,5-Dimethoxy-2,5dihydrofuran Dimethoxydimethylsilane Dimethoxydiphenylsilane 1,1-Dimethoxyethane 1,2-Dimethoxyethane (2,2⬘-Dimethoxy)ethylamine Dimethoxymethane 1,1-Dimethoxy-2methylaminoethane Dimethoxymethylvinylsilane Dimethoxymethylphenylsilane 1,2-Dimethoxy-4nitrobenzene 2,6-Dimethoxyphenol

d497 d498 d499 d500

1.190

d501 d502 d503 d504 d505 d506 d507 d508 d509 d510 d511 d512

Formula weight

Beilstein reference

Density, g/mL

Refractive index

1.055 1.03665 8

1.5240

Melting point,⬚C ⫺55 55–60 180–181

C6H4(OCH3)2 C6H4(OCH3)2 (CH3O)2C6H3CO2H

138.17 138.17 182.18

6, 813 6, 843 101, 188

(CH3O)2C6H3CO2H

182.18

10, 405

182–184

(CH3O)2C6H3COCl

200.62

103, 1402

64–66

(CH3O)2C6H3CH2OH

168.19

5, 1113

(CH3O)2C6H9OH

Boiling point,⬚C

Flash point,⬚C

877mm 213

87

Solubility in 100 parts solvent s alc, bz, eth s alc; v s bz, eth 0.05 aq; v s alc, eth

1.157

1.552020

297732mm

⬎110

160.22

1.072

1.462020

909mm

40

130.14

1.073

1.433920

160–162

47

(CH3O)2Si(CH3)2

120.23

0.880

1.369020

81.4

10

(C6H5)2Si(OCH3)2

244.4

1.077120 4

1.544720

16115mm

CH2CH(OCH3)2 CH3OCH2CH2OCH3 H2NCH2CH(OCH3)2

90.12 90.12 105.14

1, 603 1, 467 42, 758

0.850220 0.862020 4 0.965

1.366820 1.379620 1.417020

⫺113 ⫺68

64.5 85.2 13595mm

⫺17 1 53

s aq, alc, chl, eth misc aq, alc; s PE

CH2(OCH3)2 CH3NHCH2CH(OCH3)2

76.10 119.16

1, 574 42, 759

0.860120 20 0.928

1.351420 1.411520

⫺104.8

42.3 140

⫺32 29

32 aq

CH3Si(OCH3)2CH"CH2

132.24

0.884

1.395020

106

3

(CH3O)2Si(CH3)C6H5

182.3

0.99320 4

1.46920

199–200

(CH3O)2C6H3NO2

183.16

6, 789

(CH3O)2C6H3OH

154.17

6, 1081

1.1888133 4

95–98

23017mm

53–56

261

v s alc, eth; s chl ⬎110

s alc, alk; v s eth

INTERACTIVE

d494 d495 d496

Formula

ROTATED

Name

LEFT

No.

d514 d515 d516 d517 d518 d519 d520 d521 d522

1.191

d523 d524 d525 d526 d527

196.20

10, 409

96–98

(CH3O)2C6H3CN

177.20

101, 198

62–63

C6H5C(O)C(OCH3)2C6H5

256.30

C6H5CH2CH(OCH3)2

166.22

7, 293

1.004

1.495020

221

83

(CH3O)2C6H3CH2CH2NH2

181.24

13, 800

1.074

1.546420

18815mm

⬎110

CH3CH(OCH3)CH2OCH3 (CH3)2C(OCH3)2 CH3C(O)CH(OCH3)2

104.15 104.15 118.13

14, 2471 1, 648 11, 395

0.855 0.847 0.976

1.383520 1.378020 1.397820

96 83 143–147

0 ⫺11 37

(CH3O)2CHCH"CH2

102.13

11, 378

0.862

1.395420

89–90

⫺2

CH3CH"CHC6H5(OCH3)2

178.23

6, 956

1.055

1.568020

262–264

⬎110

(CH3O)2CHCH2CN

115.13

34, 521

1.026

1.413020

9230mm

86

(CH3O)2C5H3N (CH3O)2C4H6O

139.15 132.16

1.053 1.020

1.512920 1.418020

178–180 145–147

61 35

0.936625

1.437620

165.5

70

15025mm

⬎110

CH3C(O)N(CH3)2

87.12

s aq; v s alc, eth 17810mm

67–70

4, 59

CH3C(O)NHC6H3(CH3)2

163.22

12, 1109

[CH3O2CCH2]2C"O

174.15

3, 790

misc aq, alc, bz, eth

182–184 1.185

Dimethyl acetal, d504

⫺20

1.443420

Dimethylacetic acid, i81

ROTATED

3,4-Dimethoxyphenethylamine, d517 1,1-Dimethyoxytrimethylamine, d614

(CH3O)2C6H3CO2H

RIGHT

d528

3,4-Dimethoxyphenylacetic acid 3,4-Dimethoxyphenylacetonitrile 2,2-Dimethoxy-2phenylacetophenone 1,1-Dimethoxy-2phenylethane 2-(3,4-Dimethoxyphenyl)ethylamine 1,2-Dimethoxypropane 2,2-Dimethoxypropane 1,1-Dimethoxy-2propanone 3,3-Dimethoxy-1propene 1,2-Dimethoxy-4propenylbenzene 3,3-Dimethoxypropionitrile 2,6-Dimethoxypyridine 2,5-Dimethoxytetrahydrofuran N,N-Dimethylacetamide 2⬘,6⬘-Dimethylacetanilide Dimethyl 1,3-acetonedicarboxylate

DEAN 37261 (McGHP)

d513

d501

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Dimethyl acetylenedicarboxylate Dimethyl acetylsuccinate N,N-Dimethylacrylamide 3,3-Dimethylacrylic acid Dimethylaluminum chloride Dimethylamine Dimethylaminoacetonitrile 4-(Dimethylamino)benzaldehyde 3-Dimethylaminobenzoic acid 4-Dimethylaminobenzoic acid 2-(Dimethylamino)ethanol 2-[2-(Dimethylamino)ethoxy]ethanol 2-(Dimethylamino)ethyl acrylate 2-(Dimethylamino)ethyl benzoate 2-(Dimethylamino)ethyl methacrylate

d530 d531 d532

1.192

d533 d534 d535 d536 d537 d538 d539 d540 d541 d542 d543

Formula weight

Beilstein reference

Density, g/mL

Refractive index 1.447020

CH3O2CC#CCO2CH3

142.11

2, 803

1.156

CH3O2CC2CH(COCH3)CO2CH3 H2C"CHC(O)N(CH3)2

188.18

34, 1825

1.160

99.13

43, 130

0.962

(CH3)2C"CHCO2H

100.12

2, 432

Melting point,⬚C

33 1.473020

Boiling point,⬚C

Flash point,⬚C

9819mm

86

13412mm

⬎110

8120mm

71

69

195

⫺21

126–127

⫺18

⫺92.2

6.9 138

20 36

17617mm

(CH3)2AlCl

92.51

43, 1971

0.996

(CH3)2NH2 (CH3)2NCH2CN

45.08 84.12

4, 39 4, 346

0.68004 0.863

(CH3)2NC6H4CHO

149.19

14, 31

74

(CH3)2NC6H4CO2H

165.19

14, 392

148–152

(CH3)2NC6H4CO2H

165.19

14, 426

241 dec

(CH3)2NCH2CH2OH

89.14

4, 276

0.887620 4

1.429420

135

40

133.19

42, 719

0.954

1.442020

9515mm

92

143.19

43, 649

0.943

1.428020

6412mm

58

1.014

1.507720

15920mm

⬎110

0.933

1.440020

182–192

70

(CH3)2NCH2CH2OCH2CH2OH H2C"CHCO2CH2CH2N(CH3)2 C6H5CO2CH2CH2N(CH3)2 H2C"C(CH3)CO2CH2CH2N(CH3)2

193.26 157.22

43, 649

1.35017 1.410120

Solubility in 100 parts solvent

v s aq; s alc, eth

s alc, chl, eth, HOAc

s alc; sl s eth misc aq, alc, eth

INTERACTIVE

d529

Formula

ROTATED

Name

LEFT

No.

d545 d546 d547 d548 d549 d550

d551 d552

1.193

d553 d554 d555 d556 d557 d558 d559 d560

3-Dimethylaminophenol 3-Dimethylamino-1,2propanediol 1-Dimethylamino-2propanol 3-Dimethylamino-1propanol 3-(Dimethylamino)propionitrile 3-Dimethylaminopropylamine N-[3-(Dimethylamino)propyl]methacrylamide 4-(Dimethylamino)pyridine Dimethyl 2-amino-1,4phthalate N,N-Dimethylaniline 2,3-Dimethylaniline 2,4-Dimethylaniline 2,5-Dimethylaniline 2,6-Dimethylaniline 3,4-Dimethylaniline 3,5-Dimethylaniline Dimethylarsinic acid

137.18

13, 405

1.589525

(CH3)2NCH2CH(OH)CH2OH

119.16

4, 302

1.004

1.460920

216–217

105

0.837

20

1.4193

121–127

35

163–164

36

171750mm

62

82–84

265–268

v s alc, bz, eth, acet

CH3CH(OH)CH2N(CH3)2

103.17

(CH3)2NCH2CH2OH

103.17

41, 433

0.872

1.436020

(CH3)2NCH2CH2CN

98.15

43, 1265

0.870

1.425820

(CH3)2N(CH2)3NH2

102.18

43, 554

0.812

1.4350

133

15

H2C"C(CH3)CONH(CH2)3N(CH3)2

170.26

0.940

1.479020

1342mm

⬎110

(CH3)2N(C5H4N)

122.17

222, 341

112–114

H2NC6H3(CO2CH3)2

209.20

14, 559

127–130

C6H5N(CH3)2 (CH3)2C6H3NH2 (CH3)2C6H3NH2 (CH3)2C6H3NH2 (CH3)2C6H3NH2 (CH3)2C6H3NH2 (CH3)2C6H3NH2 (CH3)2As(O)OH

121.18 121.18 121.18 121.18 121.18 121.18 121.18 138.00

12, 141 12, 1101 12, 1111 12, 1135 12, 1107 12, 1103 12, 1131 4, 610

0.955920 4 0.993320 0.972320 0.979021 4 0.984220 18 1.076 0.970620

1.558420 1.568520 1.5568620 1.559220 1.560120 1.557820

Dimethylaminoacetaldehyde diethyl acetal, d300 Dimethyl 2-amino-1,4-benzenedicarboxylate, d552 Dimethyl 2-aminoterephthalate, d552

⫺43

2.5 ⬍ ⫺15 ⫺14.3 15.5 11.2 51 9.8 195–196

s aq, alc, chl, eth

v s aq, alc, bz, chl

194.2 221–222 214 214 215 228 220.5

63 97 90 93 96 98 93

v s alc, chl, eth sl s aq; s alc, eth s alc, bz, eth sl s aq; s alc, eth sl s aq; s alc, eth sl s aq; s alc sl s aq; s alc v s alc; 200 aq; i eth

N,N-Dimethylaminotrimethylsilane, d707 Dimethylanisole, d631, d632 2,4-Dimethyl-3-azapentane, d468

RIGHT ROTATED

cis-2,3-Dimethylacrylic acid, m168 trans-2,3-Dimethylacrylic acid, m169 3,3-Dimethylacrylic acid, m170 Dimethyl adipate, d617

(CH3)2NC6H4OH

DEAN 37261 (McGHP)

d544

INTERACTIVE

d561

1,3-Dimethylbarbituric acid N,N-Dimethylbenzamide 3,4-Dimethylbenzoic acid 2,5-Dimethylbenzonitrile N,N-Dimethylbenzylamine 2,3-Dimethyl-1,3butadiene 2,2-Dimethylbutane 2,3-Dimethylbutane 2,3-Dimethyl-2,3butanediol 2,3-Dimethyl-2-butanol 3,3-Dimethyl-1-butanol 3,3-Dimethyl-2-butanol 3,3-Dimethyl-2butanone 2,3-Dimethyl-1-butene 2,3-Dimethyl-2-butene 3,3-Dimethyl-1-butene N,N-Dimethylbutylamine 2,2-Dimethylbutyric acid 3,3-Dimethylbutyric acid Dimethylcadmium

d562 d563 d564 d565 d566

1.194

d567 d568 d569 d570 d570a d571 d572 d572a d573 d574 d575 d576 d577 d578

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

156.14

24, 471

124–126

C6H5CON(CH3)2

149.19

9, 201

43–45

13315mm

(CH3)2C6H3CO2H

150.18

92, 353

165–167

subl

(CH3)2C6H3CN

131.18

9, 535

0.957

1.528420

13–14

223730mm

92

C6H5CH2N(CH3)2

135.21

12, 1019

0.900

1.501120

⫺75

183

54

Solubility in 100 parts solvent

⬎110 s alc, bz

H2C"C(CH3)C(CH3)"CH2

82.15

13, 991

0.722225 4

1.436225

⫺76.0

69.2

⫺22

CH3CH2C(CH3)3 (CH3)2CHCH(CH3)2 (CH3)2C(OH)C(OH)(CH3)2

86.18 86.18 86.18

1, 150 1, 151 1, 487

0.649220 0.661620

1.368820 1.375020

⫺99.9 ⫺128.5 41.1

49.7 58.0 174.4

⫺48 ⫺29 77

v s hot aq, alc, eth

(CH3)2CHC(CH3)2OH (CH3)3CCH2CH2OH (CH3)3CCH(OH)CH3 (CH3)3CCOCH3

102.18 102.18 102.18 100.16

1, 413 13, 1677 1, 412 1, 694

0.823620 4 0.82420 0.818520 4 0.725025 25

1.417620 1.417620 1.415120 1.393925

⫺14 ⫺60 5.6 ⫺52.5

118 143 120 106

29 47 28 23

(CH3)2CHC(CH3)"CH2 (CH3)2C"C(CH3)2 (CH3)3CCH"CH2 CH3(CH2)3N(CH3)2

84.16 84.16 84.16 101.19

13, 816 1, 218 1.217 4, 1, 371

0.680 0.708120 4 0.653120 4 0.721

1.389020 1.412420 1.376220 1.398020

⫺157 ⫺75 ⫺115

55.6 73 41 93750mm

⫺18 ⫺16 ⫺28 ⫺3

C2H5C(CH3)2CO2H

116.16

2, 335

0.928

1.415420

965mm

79

(CH3)3CCH2CO2H

116.16

2, 337

0.912420 4

1.410020

6–7

190

88

s alc, eth

(CH3)2Cd

142.48

1.984617 4

1.5488

⫺4.5

105.5

⬎150 explodes

dec aq; s PE

s aq; misc alc, eth s alc; misc eth 2.5 aq; s alc, eth

s alc, eth

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

INTERACTIVE

d580 d581 d582 d583 d584 d584a d585 d586 d587

1.195

d587a d588 d589

Dimethylcarbamyl chloride Dimethyl carbonate Dimethyl chloromalonate Dimethyl chlorothiophosphate Dimethylcyanamide Dimethyl N-cyanothioiminocarbonate 1,1-Dimethylcyclohexane cis-1,2-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane cis-1,3-Dimethylcyclohexane trans-1,3-Dimethylcyclohexane cis-1,4-Dimethylcyclohexane 5,5-Dimethyl-1,3cyclohexanedione

(CH3)2NCOCl

107.54

4, 73

1.168

1.454020

⫺33

168

68

(CH3O)2C"O ClCH(CO2CH3)2

90.08 166.56

3, 4 2, 592

1.06517 4 1.305

1.368220 1.437020

0.5

90–91 10619mm

18 106

(CH3O)2P(S)Cl

160.56

11, 143

1.322

1.481920

6716mm

105

(CH3)2NCN (CH3S)2C"NCN

70.09 146.23

4, 74 3, 220

0.867

1.410020

161–163

58 110

(CH3)2C6H10

112.22

5, 35

0.777

1.428020

⫺33

120

7

(CH3)2C6H10

112.22

5, 36

0.796320

1.433520

⫺49.9

129.7

16

i aq; s alc, bz

(CH3)2C6H10

112.22

5, 36

0.776020

1.427320

⫺90

123.4

11

i aq; s alc, bz

(CH3)2C6H10

112.22

5, 36

0.784

1.423020

⫺76

120

5

(CH3)2C6H10

112.22

52, 21

0.780

1.430520

⫺90

124.5

7

(CH3)2C6H10

112.22

52, 22

0.783

1.429720

⫺88

125

6

140.18

7, 559

dec 149

Dimethyl 1-butynedioate, d529 Dimethyl cellosolve, d505 Dimethylchlorosilane, c93

cis-2-Dimethylcrotonic acid, m168 trans-2-Dimethylcrotonic acid, m169

0.4 aq; s alc, bz

RIGHT

Dimethylbenzenes, x4, x5, x6 6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-ethanol, n106 Dimethyl cis-butenedioate, d628

46–50

i aq; misc alc, eth

DEAN 37261 (McGHP)

d579

ROTATED

d561

d589

INTERACTIVE

d590

2,3-Dimethylcyclohexanol 3,5-Dimethylcyclohexanol 2,6-Dimethylcyclohexanone N,N-Dimethylcyclohexylamine 2,3-Dimethylcyclohexylamine 1,5-Dimethyl-1,5cyclooctadiene Dimethyl 1,1-cyclopropanedicarboxylate Dimethyl decanedioate 2,2-Dimethyl-1,3dioxane-4,6-dione 2,2-Dimethyl-1,3dioxolane-4-methanol Dimethyl disulfide Dimethyldithiocarbamic acid, Zn salt N,N-Dimethyldodecylamine Dimethyl ether

d591 d592 d593 d594 d595

1.196

d596

d597 d598 d599

d600 d601

d602 d603 d604

Formula weight

Beilstein reference

Density, g/mL

Refractive index

0.934

1.465320

(CH3)2C6H9OH

128.22

(CH3)2C6H9OH

128.22

6, 18

0.892

1.4552

(CH3)2C6H8("O)

126.20

7, 23

0.925

C6H11N(CH3)2

127.23

(CH3)2C6H9NH2

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

65 11–12

186

73

1.446020

175

51

0.849

1.453520

159

42

127.23

0.835

1.459520

160

51

136.24

0.867

1.489620

7416mm

55

196–198

95

1445mm

145

i aq; s alc, eth s aq, acet

188–189

80

misc aq, alc, bz, esters, eth, PE, acetals i aq; misc alc, eth ⬍ 0.2 alc, eth; ⬍ 0.5 acet, bz; 0.5 naphtha

C3H4(CO2CH3)2

158.16

91, 314

1.147

1.441020

CH3O2C(CH2)8CO2CH3

230.30 144.13

2, 719

0.98330 20

1.433528

132.16

19, 65

1.063

1.434020

CH3SSCH3 [(CH3)2NCS2]2Zn

94.20 305.80

1, 291 43, 149

1.062520 1.66

1.528920

⫺84.7 250–252

109.8

24

CH3(CH2)11N(CH3)2

213.41

43, 409

0.775

1.437520

⫺20

1123mm

⬎110

(CH3)2O

46.07

1, 281

0.66120

⫺141.5

⫺24.9

⫺41

C2H5N(CH3)2

73.14

4, 94

0.675

1.372020

⫺140

36–38

⫺36

C2H5NCH2CH2NH2

88.15

42, 690

0.803

1.426020

106

23

23 94–96

i aq; s alc, eth

35 aq(5 atm); 15 bz; 11.8 acet

INTERACTIVE

d605

N,N-Dimethylethylamine N,N-Dimethylethylenediamine

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

d607

d608 d609 d610 d611 d612 d613 d613a d614

1.197

d615 d616 d616a d617 d618

N,N-Dimethylformamide N,N-Dimethylformamide dimethyl acetal Dimethyl fumarate 2,5-Dimethylfuran Dimethylglyoxime 2,4-Dimethyl-1,6heptadienal 2,4-Dimethyl-2,6heptadien-1-ol 2,6-Dimethyl-2,5heptadien-4-one 2,2-Dimethylheptane Dimethyl heptanedioate 2,6-Dimethyl-4heptanol 2,6-Dimethyl-4heptanone 2,4-Dimethylhexane Dimethyl hexanedioate 2,5-Dimethyl-2,5hexanediol

(CH3)2NCHO

0.944525 4

1.430520

0.897

1.397220

1.045106 0.900020 4

1.441420

138.21

0.870

140.23

73.10

(CH3)2NCH(OCH3)2

119.16

CH3O2CCH"CHCO2CH3 (CH3)2(C4H2O) CH3C("NOH)C("NOH)CH3 H2C"CHCH2CH(CH3)CH"C(CH3)CHO H2C"CHCH2CH(CH3)CH"C(CH3)CH2OH (CH3)2C"CHC("O)CH"(CH3)2 (CH3)3C(CH2)4CH3 CH3O2C(CH2)5CO2CH3

144.13 96.13 116.12

4, 58

2, 741 17, 41 1, 772

153.0

57

103720mm

7

193 93

⫺1

1.466420

472mm

64

1.351

1.464020

8610mm

78

105 ⫺62 240

misc aq, alc, bz, eth

sl s alc, eth i aq; misc alc, eth s alc, acet, eth, pyr

138.21

1, 751

0.88520 4

1.496821

28

198–199

79

sl s aq; s alc, eth

128.26 188.22

21, 281

0.710520 1.062520 4

1.401620 1.431420

⫺113 ⫺21

132.7 12211mm

⬎110

s alc

178

66

⫺41.5

169.4

49

8 86–90

109.5 11210mm 214–215

10 107 126

(CH3)2CHCH2CH(OH)CH2CH(CH3)2 [(CH3)2CHCH2]2C"O

144.26

1, 425

0.809

1.423620

142.24

1, 710

0.80620 20

1.411420

C2H5CH(CH3)CH2CH(CH3)2 CH3O2C(CH2)4CO2CH3 [(CH3)2C(OH)CH2⫺]2

114.23 174.20 146.23

1, 162 1, 652 1, 492

0.696225 1.060020 4

1.392925 1.428520

N,N-Dimethylethanolamine, d539 (1,1-Dimethylethyl)benzene, b523 4-(1,1-Dimethylethyl)-4-methylbenzene, b602

4-(1,1-Dimethylethyl)phenol, b588 Dimethyl glutarate, d656

0.06 aq; misc alc, bz, chl, eth i aq; s alc, eth

RIGHT

Dimethyl diphenyl sulfone 4,4⬘-dicarboxylate, s29 Dimethyleneimine, e148 Dimethylene oxide, e146

⫺60.4

DEAN 37261 (McGHP)

d606

ROTATED

d595

d598

d599

INTERACTIVE

1.420920

126.20

12, 507

0.859

128.13

24, 289

(CH3)2NNH2 CH3NHNHCH3

60.10 60.10

4, 547 4, 547

0.79122 4 0.827420 4

1.407520 1.420920

(CH3O)2P(O)H

110.05

1, 285

1.20020 4

1.400920

96.13 114.15

23, 66

1.084 1.044

87.17

42, 630

CH3O2CCH"CHCO2CH3 CH3O2CCH2CO2CH3 (CH3)2Hg (CH3)2C6H3OCH3

144.13 132.12 230.66 136.19

(CH3)2C6H3OCH3

(CH3)2CH(CH2)3CH(NH2)CH3 (CH3)2C(OH)C#CC(OH)(CH3)2 (CH3)2CHCH2C(CH3)(OH)C#CH

d622

1,5-Dimethylhexylamine 2,5-Dimethyl-3hexyne-2,5-diol 3,5-Dimethyl-1hexyn-3-ol 5,5-Dimethylhydantoin

d623 d624

1,1-Dimethylhydrazine 1,2-Dimethylhydrazine

d625

Dimethyl hydrogen phosphonate 1,2-Dimethylimidazole 1,3-Dimethyl-2imidazolidinone N,N-Dimethylisopropylamine Dimethyl maleate Dimethyl malonate Dimethylmercury 3,4-Dimethyl-1methoxybenzene 3,5-Dimethyl-1methoxybenzene Dimethyl methylmalonate Dimethyl methylphosphonate Dimethyl methylsuccinate 2,6-Dimethylmorpholine

d621

d626 d627 d628 d629 d630 d631 d632 d633 d634 d635 d636 d637

Beilstein reference

129.25

Melting point,⬚C

Boiling point,⬚C 154–156

94–95 1.433520

Flash point,⬚C 48

205–206 151

44

176–178 ⫺58

Solubility in 100 parts solvent

170–171

1 flammable 29

1.472020

204 10817mm

92 80

0.715

1.390520

66

⫺9

2, 751 2, 572 4, 678 6, 481

1.160620 1.15420 4 3.187420 0.974414 4

1.442220 1.413520 1.545220 1.519814

202 180–181 92–94 200

113 90 5

8.7 aq sl s aq; misc alc, eth i aq; s alc, eth i aq; s alc, bz, eth

136.19

6, 493

0.962715 4

1.510715

193

65

i aq; s alc, bz, eth

CH3CH(CO2CH3)2

146.14

2, 628

1.098

1.414020

176–177

76

(CH3O)2P(O)CH3

124.08

41, 572

1.145

1.413020

181

68

CH3O2CCH2CH(CH3)CO2CH3

160.17

23, 1696

1.076

1.420020

196

83

0.934620

1.447020

147

48

(CH3)2CHN(CH3)2

115.18

29–30

⫺19 ⫺62 ⫺43

⫺85

63.9 81

v s aq, alc, bz, chl, eth, acet misc aq, alc, eth, PE misc aq, alc, eth, PE s aq(hyd); misc alc, acet, eth

misc aq, alc, bz

INTERACTIVE

d619

Formula weight

ROTATED

0.767

142.20

Merck: 11, 6678 1, 501

Formula

LEFT

Refractive index

Name

d620

1.198

Density, g/mL

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

d646

1,2-Dimethylnaphthalene 1,2-Dimethyl-3-nitrobenzene 1,2-Dimethyl-4-nitrobenzene 1,3-Dimethyl-2-nitrobenzene 1,3-Dimethyl-4-nitrobenzene N,N-Dimethyl-4nitrosoaniline Dimethyl 2-nitro-1,4phthalate cis-3,7-Dimethyl-2,6octadienal trans-3,7-Dimethyl2,6-octadienal 3,7-Dimethyl-1-octanol

d647

3,7-Dimethyl-3-octanol

d638 d639 d640 d641 d642 d643 d644 d645

C10H6(CH3)2

156.23

51, 267

1.017920

1.616620

0.8

266.5

⬎110

(CH3)2C6H3NO2

151.17

5, 367

1.129

1.543420

7–9

245

107

i aq; s alc

29–31

143

⬎110

i aq; s alc

1.522020

14–16

225744mm

87

i aq; s alc

1.549720

2

237–239

107

s alc, bz, chl, eth

12, 677

86

flammable solid

9, 826

72–75

(CH3)2C6H3NO2

151.17

5, 368

1.139

(CH3)2C6H3NO2

151.17

5, 378

1.112

(CH3)2C6H3NO2

151.17

5, 378

1.117

(CH3)2NC6H4NO

150.18

O2NC6H3⫺1,4-(CO2CH3)2

239.18

1.199

(CH3)2CH(CH2)3CH(CH3)CH2CH2OH (CH3)2CH(CH2)3C(OH)(CH3)C2H5

Dimethyl isophthalate, d669 1,4a-Dimethyl-7-isopropyl-1,2,3,4,4a,9,10,10a-octahydro-1phenanthrenemethylamine, d24

20mm

i aq; s alc, eth

152.24

0.888820 4

1.489820

229

101

misc alc, eth, glyc

152.24

0.886920 4

1.486920

229

101

misc alc, eth, glyc

158.29

1, 426

0.840

1.435520

969mm

95

158.29

1, 426

0.826

1.433620

736mm

76

Dimethyl ketone, a26 2,2-Dimethyl-3-methoxyoxirane, m86 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane, p176

DEAN 37261 (McGHP)

d637a

2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane, c2 2,2-Dimethyl-3-methylenenorbornane, c2 6,6-Dimethyl-2-methylenenorpinene, p176

RIGHT ROTATED

d622

d626

d627

d637

d644

d645

INTERACTIVE

0.811

1.542920

157.30

41, 386

0.765

1.424320

170.35

11, 263

C2H5CH(CH3)CH(CH3)2 (CH3)2CHCH2CH(CH3)2 CH3O2C(CH2)3CO2CH3

202.25 118.09 86.13 100.21 100.21 160.17

2, 693 2, 534 172, 21 12, 120 1, 158 2, 633

1.021020 4 1.14854 0.835 0.695120 4 0.672720 1.087620

1.432520 1.37980 1.3990 1.392020 1,381520 1.424420

(CH3)2CHCH(OH)CH(CH3)2

116.20

1, 417

0.82920 4

1.425420

(CH3)2CHC(O)CH(CH3)2

114.19

1, 703

0.806220 4

1.398620

(CH3)2C6H3OH (CH3)2C6H3OH (CH3)2C6H3OH (CH3)2C6H3OH (CH3)2C6H3OH (CH3)2C6H3OH (CH3)2NC6H4NH2

122.17 122.17 122.17 122.17 122.17 122.17 136.20

6, 480 6, 486 6, 494 6, 485 6, 480 6, 492 13, 72

1.542020 1.542014

175.23

274, 1114

136.24

C2H5C(CH3)(OH)C#CC(CH3)(OH)C2H5 CH3O2C(CH2)6CO2CH3 CH3O2CCO2CH3

d669 d670

Dimethyl 1,3-phthalate Dimethyl 1,4-phthalate

d650 d651 d652 d653 d654 d655 d656 d657 d658 d659 d660 d661 d662 d663 d664 d665 d666 d667

1.027614 4 0.96580 0.983020 0.968020

1.025

C6H5CH2C(CH3)2CH2OH

164.25

C6H4(CO2CH3)2

194.19

9, 797

1.190520

C6H4(CO2CH3)2 C6H4(CO2CH3)2

194.19 194.19

9, 834 9, 843

1.19420 4

1.532220

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

7514mm

68

⫺57

195

65

53–55

214680mm

⬎110

⫺4.8 50–54

268 163.5 81 89.8 80.4 214

75 ⫺9 ⬍⫺7 ⫺12 102

i aq; s alc, eth

140

37

sl s aq; s alc, eth

⫺69

125

15

72.8 24.5 74.5 45.7 60.8 64 36

217 211 211.5 201 227 222 262

20–24

12420mm

102

15mm

⫺120 ⫺42.5

⬎110 73

90

35

126

109

1.513820

5.5

283.7

146

1.516820

67–68 140–142

282 288

i aq; s alc 6 aq; s alc, eth

v s alc, eth

v s alc, bz, chl, eth v s alc, bz, chl, eth v s alc, bz, chl, eth v s alc, bz, chl, eth v s alc, bz, chl, eth v s alc, bz, chl, eth v s aq; s alc

0.4 aq; misc alc, chl, eth; i PE i aq 0.3 hot aq; s hot alc; s eth

INTERACTIVE

CH3CH"C(CH3)CH"CHCH"C(CH3)2 CH3(CH2)7N(CH3)2

d668

2,6-Dimethyl-2,4,6octatriene N,N-Dimethyloctylamine 3,6-Dimethyl-4octyne-3,6-diol Dimethyl octanedioate Dimethyl oxalate 3,3-Dimethyloxetane 2,3-Dimethylpentane 2,4-Dimethylpentane Dimethyl pentanedioate 2,4-Dimethyl-3pentanol 2,4-Dimethyl-3pentanone 2,3-Dimethylphenol 2,4-Dimethylphenol 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol 3,5-Dimethylphenol N,N-Dimethyl-1,4phenylenediamine 4,4-Dimethyl-2phenyl-2-oxazoline 2,2-Dimethyl-3phenyl-1-propanol Dimethyl 1,2-phthalate

Melting point,⬚C

ROTATED

13, 1050

d648

Beilstein reference

LEFT

Refractive index

Name

d649

1.200

Density, g/mL

Formula

Formula weight

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

d672 d673 d674 d675 d676 d677 d678 d679

1.201

d680 d681 d682

1,4-Dimethylpiperazine cis-2,6-Dimethylpiperidine 2,2-Dimethylpropane 2,2-Dimethyl-1,3propanediamine 2,2-Dimethyl-1,3propanediol 2,2-Dimethyl-1propanol 2,2-Dimethylpropionaldehyde N,N-Dimethylpropionamide 2,2-Dimethylpropionic acid 2,2-Dimethylpropionic anhydride 2,2-Dimethylpropionyl chloride 1,1-Dimethylpropylamine

(CH3)4C

114.19

23, 7

0.844

1.446320

132750mm

18

113.20

20, 108

0.840

1.439420

127

11

72.15

0.613

1.3476

⫺16.6

9.5

⫺65

0.851

1.456620

31

154

47

0

6

H2NCH2C(CH3)2CH2NH2

102.18

Merck: 12, 6545 43, 595

(CH3)2C(CH2OH)2

104.15

1, 483

1.1125

127–128

208–210

107

88.15

1, 406

0.81220 4

52.5

113.1

36

(CH3)3CCH2OH

180 aq; 12 bz; 60 acet; v s alc, eth 3.6 aq; misc alc, eth

0.793

1.379420

6

74730mm

⬍1

43, 126

0.920

1.440020

⫺45

175

62

102.13

2, 319

0.90550

1.393137

35.5

163.8

63

[(CH3)3DD(O)]2O

186.25

2, 320

0.918

1.409220

193

57

(CH3)3CC(O)Cl

120.58

2, 320

0.979

1.412020

105–106

⬍1

dec aq, alc; v s eth

87.17

4, 179

0.73125 4

1.399620

77

65

misc aq, alc, eth

(CH3)3CCHO

186.25

C2H5C(O)N(CH3)2

101.15

(CH3)3CCO2H

CH3CH2C(CH3)2NH2

1,5-Dimethyl-2-phenyl-4-aminopyrazolone, a110 2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one, a299 Dimethyl phosphite, d625

Dimethyl pimelate, d617 Dimethyl propanedioate, d630 1,1-Dimethylpropargylamine, d683

2.5 aq; v s alc, eth

RIGHT

3,7-Dimethyl-6-octen-1-ol, c275 Dimethylolpropionic acid, b201 Dimethyl 3-oxoglutarate, d325

⫺105

DEAN 37261 (McGHP)

d671

ROTATED

d653

d666

d671

d672

INTERACTIVE

No. d683 d684 d685 d686 d687 d688 d689 d690 d691 d692

1.202

d693

d702

d703 d704

HC#CC(CH3)2NH2

Dimethyl sulfide Dimethyl sulfite Dimethyl sulfone Dimethyl sulfoxide Dimethyl-d6 sulfoxide (⫹)-Dimethyl Ltartrate Dimethyltelluride 2,5-Dimethyltetrahydrofuran 1,3-Dimethyl-3,4,5,6tetrahydro-2(1H)pyrimidinone Dimethyl 3,3⬘-dithiopropionate N,N-Dimethylthioformamide N,N⬘-Dimethylthiourea

Beilstein reference

83.13

Density, g/mL

Refractive index

0.790

1.423520

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

79–80

2

108 ⫺15 ⬍ ⫺64 ⫺6.0 ⫺12 ⫺9

218 163 158.3 144 164 170 465mm

50 37 33 53 53 80

Solubility in 100 parts solvent

(CH3)2(C5H3N) (CH3)2(C5H3N) (CH3)2(C5H3N) (CH3)2(C5H3N) (CH3)2(C5H3N) O(CO2CH3)2

96.13 107.16 107.16 107.16 107.16 107.16 134.09

23, 74 20, 243 20, 244 20, 244 20, 246 20, 246 34, 17

0.945 0.930920 0.922620 0.95425 4 0.93925 4 1.250

1.5080 1.501020 1.495620 1.510025 1.503325 1.393320

CH3O2CCH2CH2CO2CH3 (CH3)2NSO2Cl

146.14 143.59

2, 609 4, 84

1.119820 1.337

1.419020 1.451820

19

196.4 11475mm

85 94

0.83 aq; 2.9 alc

(CH3O)2SO2

126.13

1, 283

1.332220 4

1.387420

⫺31.8

188 dec

83

(CH3)2S (CH3O)2SO (CH3)2SO2 (CH3)2SO (CD3)2SO CH3O2CH(OH)CH(OH)CO2CH3 (CH3)2Te (CH3)2(C4H2O)

62.13 110.13 94.13 78.13 84.18 178.14

1, 288 1, 282 1, 289 1, 289 14, 1279 3, 510

0.848320 1.294

1.443820 1.408320

⫺98.3

1.10120 4 1.190 1.32820 4

1.417020 1.475820

37.3 126–127 238 189.0 555mm 16323mm

⫺36 30 143 95 95 ⬎110

2.8 aq(hyd); s acet, bz, dioxane, eth 2 aq; s alc, eth

157.68 100.16

1, 291 17, 14

0.833

1.4041

91–92 90–92

26

128.18

243, 32

1.060

1.488020

14644mm

⬎110

1.198

1.474020

14818mm

⬎110

1.047

1.575720

581mm

99

(CH3O2CCH2CH2)2S

206.26

(CH3)2NC(S)H

89.16

4, 70

(CH3NH)2C"S

104.18

4, 70

109 18.5 48–50 ⫺10

60–62

s aq; v s bz, eth 17 aq; v s alc, bz, eth 43 aq45; s alc, eth sl s aq; s alc, eth s aq, alc, eth

v s aq, alc, acet s alc, acet, bz, chl s aq; 200 alc15; v s bz dec aq; v s alc; i eth

v s aq, alc, acet

INTERACTIVE

d705

1,1-Dimethyl-2propynylamine 3,5-Dimethylpyrazole 2,3-Dimethylpyridine 2,4-Dimethylpyridine 2,6-Dimethylpyridine 3,4-Dimethylpyridine 3,5-Dimethylpyridine Dimethyl pyrocarbonate Dimethyl succinate Dimethylsulfamoyl chloride Dimethyl sulfate

Formula weight

ROTATED

d700 d701

Formula

LEFT

d694 d695 d696 d697 d698 d699

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

1.545820

211

83

0.732

1.397020

84

⫺19

⫺1

CH3C6H4N(CH3)2

135.21

(CH3)3SiN(CH3)2

117.27

d708 d709

(CH3NH)2C"O (CH3)2Zn

88.11 95.45

d710 d711

2,4-Dinitroaniline 1,3-Dinitrobenzene

(O2N)2C6H3NH2 C6H4(NO2)2

183.12 168.11

4, 65 Merck: 12, 3312 12, 747 5, 258

d712

2,4-Dinitrobenzenesulfenyl chloride 3,5-Dinitrobenzoic acid 3,5-Dinitrobenzoyl chloride 2,6-Dinitro-p-cresol 4,6-Dinitro-o-cresol 2,4-Dinitrodiphenylamine 2,4-Dinitro-1-fluorobenzene 1,5-Dinitronaphthalene

(O2N)2C6H3SCl

234.62

62, 316

96

(O2N)2C6H3CO2H

212.12

9, 413

205–207

(O2N)2C6H3COCl

230.56

9, 414

69–71

(O2N)2C6H2(OH)CH3 (O2N)2C6H2(OH)CH3 (O2N)2C6H3NHC6H5

198.13 198.13 259.22

6, 414 6, 368 12, 751

77–79 83–87 159–161

FC6H3(NO2)2

186.10

5, 262

C10H6(NO2)2

218.17

5, 558

d707

d713 d714

1.203

d715 d716 d717 d718 d719

0.724

101–104 ⫺40

268–270 46

1.61514 1.368

176–178 89–90

297

1.569020

1.482

Dimethyl suberate, d651 Dimethyl terephthalate, d670

v s aq, alc; i eth misc bz, PE; s eth i aq; 0.75 alc 0.05 aq; 2.7 alc; v s bz, chl, EtOAc s bz, HOAc; dec alc 1.9 hot aq; v s alc; sl s bz, eth dec aq, alc; s eth

19611mm

v s alc, acet, eth, alk

27–30

17825mm

216–217

subl

⬎110

s bz, eth, glyc s bz; v s eth; sl s alc

2,4-Dinitrochlorobenzene, c114 3,4-Dinitrochlorobenzene, c115

RIGHT

1,3-Dimethyl-2,4,6(1H,3H,5H)pyrimidinetriol, d561 N⬘-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide, s22 Dimethyl sebacate, d597

12, 902

0.937

N,N-Dimethyl-ptoluidine N,N-Dimethyltrimethylsilylamine 1,3-Dimethylurea Dimethylzinc

DEAN 37261 (McGHP)

d706

ROTATED

d684

d702

INTERACTIVE

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Boiling point,⬚C

Flash point,⬚C

2,4-Dinitrophenol

(O2N)2C6H3OH

184.11

6, 251

d721

(O2N)2C6H3NHNH2

198.14

15, 489

ca. 200

(O2N)2C6H2(OH)CO2H

228.12

10, 122

169–172

s aq; v s alc, eth

CH3C6H3(NO2)2 CH3C6H3(NO2)2 C9H19O2C(CH2)4CO2C9H19 (C18H37O)2P(O)H S[CH2CH2CO2(CH2)17CH3]2

182.14 182.14 398.63 586.97 683.18

5, 339 5, 341

(C8H17)2NH (C8H17)2O (C8H17)2S H2N(CH2)3O(CH2)4O(CH2)3NH2

241.46 242.45 258.51 204.32

4, 196 1, 419 1, 419

0.799 0.806 0.842 0.962

1.443220 1.431820 1.461020 1.460920

14–16 ⫺7.6

298 287 18010mm 1364mm

⬎110 ⬎110 ⬎110 ⬎110

d732 d733

2,4-Dinitrophenylhydrazine 3,5-Dinitrosalicylic acid 2,4-Dinitrotoluene 2,6-Dinitrotoluene Dinonyl hexanedioate Dioctadecyl phosphite Dioctadecyl 3,3⬘thiopropionate Dioctylamine Dioctyl ether Dioctyl sulfide 4,9-Dioxa-1,12dodecanediamine 1,3-Dioxane 1,4-Dioxane

s alc, bz; 16 EtOAc; 36 acet; 5 chl; 20 pyr sl s aq, alc; s acid

88.11 88.11

19, 2 19, 3

1.032 1.032920 4

1.418020 1.422420

⫺45 11.8

106 101.2

15 12

d734 d735

1,3-Dioxolane Dipentaerythritol

74.08 254.28

192, 2

1.06020 4

1.400020

⫺95 215–218

78

2

d736 d737 d738 d739

Dipentene Dipentylamine Dipentyl ether N,N-Diphenylacetamide Diphenylacetic acid Diphenylacetonitrile Diphenylacetylene Diphenylamine

136.24 157.29 158.29 211.26

5, 137 41, 378 11, 193 12, 247

0.840221 4 0.777 0.783320 4

1.473920 1.4272 1.412020

⫺95.5

(C5H11)2NH (C5H11)2O CH3CON(C6H5)2

⫺69.4 103

178 195–202 190 1300.02mm

45 52 57

(C6H5)2CHCO2H (C6H5)2CHCN C6H5C#CC6H5 (C6H5)2NH

212.25 193.25 178.23 169.23

9, 673 9, 674 5, 656 12, 174

1.25815 15

148 71–73 62.5 53

1955mm 18112mm 300 302

d723 d724 d725 d726 d727

1.204

d728 d729 d730 d731

1.442 1.479

67–70 64–66

300 sl d

1.2 alc; 9 eth s alc 218

57–59 65–67

misc aq, alc, bz, chl, eth, PE misc aq; s alc, eth

i aq; misc alc v s alc, eth misc alc, eth; s acet sl s aq; s alc, eth

ROTATED

s hot aq, alc, chl, eth

152

v s eth, hot alc 45 alc; v s bz, eth

INTERACTIVE

0.990 1.160

i aq; v s alc, eth

LEFT

d740 d741 d742 d743

(HOCH2)3CCH2OCH2C(CH2OH)3

1.32171 1.2833111 0.91725 25

106–108

Solubility in 100 parts solvent

d720

d722

1.683

Melting point,⬚C

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

d745 d746 d747 d748 d749 d750 d751 d752 d753 d754 d755

5, 676

0.997422 4

cis,trans-1,4-Diphenyl1,3-butadiene Diphenylcarbamoyl chloride 1,5-Diphenylcarbohydrazide Diphenyl carbonate Diphenyl chlorophosphate Diphenyl diselenide Diphenyl disulfide Diphenylenimine

C6H5CH"CHCH"CHC6H5

206.29

(C6H5)2NC(O)Cl

231.68

(C6H5NHNH)2C"O

242.28

15, 292

(C6H5O)2C"O (C6H5O)2P(O)Cl

214.22 268.64

6, 158 6, 179

1.296

C6H5SeSeC6H5 C6H5SSC6H5

312.13 218.34 167.21

6, 346 6, 323 20, 433

1.55780 4 1.35320 4 18 1.104

1,2-Diphenylethane Diphenyl ether N,N⬘-Diphenylformamidine 1,3-Diphenylguanidine

C6H5CH2CH2C6H5 C6H5OC6H5 C6H5N"CHNHC6H5

182.27 170.21 196.25

5, 598 6, 146 12, 236

0.99520 4 1.066130 4

C6H5NHC("NH)NHC6H5

211.27

12, 369

1.13

149.7

350720mm

s alc; sl s eth

82–84 168–171 80–81

1.205

Diphenic acid, b141 Diphenolic acid, b205 Diphenyl, b138 Diphenylacetone, d767 Diphenylbenzenes, t7 thru t9 sym-Diphenylcarbazide, d746 Diphenyldiazene, a312

1,3-Dioxacyclohexane, d732 1,4-Dioxacyclohexane, d733 1,3-Dioxacyclopentane, d734 3,6-Dioxa-1,11-undecanediol, t430 (2,5-Dioxo-4-imidazolidinyl)urea, a71 1,3-Dioxolane-2-one, e132 Dipentyl ketone, u11

1.065322

1.550020 61–63 58–60 246 1.5338 1.576330

s hot alc, acet, HOAc 301–302 316272mm

s hot alc, bz, eth ⬎110

310 355

52.5 26.9 138–141

284 258

148–150

dec 170

⬎110 112

s hot alc s alc, bz, eth; i aq 0.8 bz; 3 eth; 16 pyr; 11 acet; i aq s alc; v s chl, eth s alc, bz, eth, HOAc s eth; v s chl

DEAN 37261 (McGHP)

d744

s alc, hot bz, chl

Diphenylenemethane, f2 Diphenylethanedione, b35 Diphenylethanedione dioxime, b36 1,2-Diphenylethene, s9 Diphenylethyne, d742 Diphenylglycolic acid, b37 Diphenylglyoxime, b36

RIGHT ROTATED

d732

d733

d734

d736

d751

INTERACTIVE

5,5-Diphenylhydantoin 1,2-Diphenylhydrazine Diphenylmercury Diphenylmethane Diphenylmethanol

d761

1,1-Diphenylmethylamine 2,5-Diphenyloxazole Diphenyl phosphite Diphenylphosphoryl azide Diphenyl o-phthalate 2,2-Diphenyl-1-picrylhydrazyl 1,3-Diphenyl-2propanone 2,2-Diphenylpropionic acid Diphenylsilanediol Diphenyl sulfide Diphenyl sulfone Diphenyl sulfoxide Diphenylthiocarbazone 1,3-Diphenyl-2-thiourea 1,3-Diphenylurea Dipiperidinomethane Dipropylamine 3-Dipropylamino-1,2propanediol Dipropylene glycol Dipropylene glycol butyl ether

d762 d763 d764

1.206

d765 d766 d767 d768 d769 d770 d771 d772 d773 d774 d775 d776 d777 d778 d779 d780

Formula weight

Beilstein reference

Density, g/mL

Refractive index

C6H5NHNHC6H5 (C6H5)2Hg C6H5CH2C6H5 C6H5CH(OH)C6H5

252.27 184.24 354.81 168.24 184.24

24, 410 15, 123 16, 946 52, 498 6, 678

1.15816 4 2.3184 1.006

1.576820

C6H5CH(NH2)C6H5

183.25

12, 1323

1.063522 4

1.595699

(C6H5O)2P(O)H (C6H5O)2P(O)N3

221.26 234.19 275.20

27, 78 61, 94

1.223 1.277

1.557520 1.551820

C6H4(CO2C6H5)2

318.33 394.32

9, 801 162, 363

C6H5CH2(C"O)CH2C6H5

210.28

7, 445

CH3C(C6H5)2CO2H

226.28

92, 474

(C6H5)2Si(OH)2 (C6H5)2S (C6H5)2SO2 (C6H5)2SO C6H5N"NC(S)NHNHC6H5 C6H5NHC(S)NHC6H5

216.31 186.28 218.27 202.28 256.33 228.32

16, 909 6, 299 6, 300 6, 300 16, 26 12, 394

C6H5NHC(O)NHC6H5

212.35 182.31 101.19 175.27

12, 352

134.18 190.29

(C3H7)2NH (C3H7)2NCH2CH(OH)CH2OH HO(CH2)3O(CH2)3OH CH3CH(OH)CH2OCH2CH(OC4H9)CH3

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

294–297 123–126 128–129 25 66.7

dec ⬎306 265 298

⬎110

34

295

⬎112

72–74 12

360 21926mm 1570.17mm

176 ⬎110

Solubility in 100 parts solvent i aq; 1.7 alc; 3.3 acet v s alc; sl s bz s chl; sl s hot alc v s alc, bz, chl, eth 0.05 aq; v s alc, chl, eth sl s aq

74–76 127 dec 1.2

1.11815 15

1.632720

1.32

4, 138 43, 841

1.239 0.915 0.737520 4 0.949

1.482020 1.404320 1.455420

12, 537 1, 4, 2474

1.023 0.91725 25

1.441020 1.42525

32–34

330

i aq; v s alc, eth

175–177

300

s alc; v s bz, eth

140 dec ⫺40 128–129 69–71 168 dec 154 238 ⫺63

296 379 20713mm

53 ⬎110

misc bz, eth, CS2 i aq; s hot alc, bz i aq; v s chl, CCl4 i aq; v s alc, eth

260 dec 12315mm 109.2 1439mm

91 17 ⬎110

0.015 aq; s eth, HOAc

229

137 96

4 aq; v s alc, eth, PE

INTERACTIVE

d756 d757 d758 d759 d760

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

(CH3)3CO(CH2)3O(CH2)3OH

190.29

[C6H5CO2(CH2)3]2O

342.40

d786 d787 d788 d789 d790

Dipropylene glycol tert-butyl ether Dipropylene glycol dibenzoate Dipropylene glycol isopropyl ether Dipropylene glycol methyl ether Dipropylene glycol acetate Dipropyl ether Dipropyl hexanedioate Dipropyl sulfate Dipropyl sulfone 2,2⬘-Dipyridyl

d791

Disilane

H3SiSiH3

d782 d783 d784 d785

CH3CH(OH)CH2OCH2CH[OCH(CH3)2]CH3 CH3CH(OH)CH2OCH2CH(OCH3)CH3 CH3CO2(CH2)3O(CH2)3OCH3 (C3H7)2O C3H7O2C(CH2)4CO2C3H7 (C3H7O)2SO2 (C3H7)2SO2

1.424020

220–222

87

1.120

1.528020

2325mm

⬎110

80.1

90

188.3

74

200

85

⫺126.2 ⫺20 dec 140 28–30 70–73

89.6 14410mm 12020mm 270 273

21

⫺132

⫺14.3

ignites in air

25 25

25

176.2

0.878

1.421

148.2

0.95120 20

1.41920

190.24

0.970

1.418020

1, 354 22, 574 1, 354 1, 359 23, 199

0.746620 0.979020 4 1.10620 4 1.02850 4

1.380320 1.431420

Merck: 12, 3419

0.686⫺425

102.18 230.30 182.24 150.24 156.19 62.22

1.207

5,5-Diphenyl-2,4-imidazolidinedione, d756 Diphenyl ketone, b53 Diphenylmethanone, b53 1,1-Diphenylmethylamine, a159 Diphenyl oxide, d753

92, 108

0.900

Diphenylphosphorochloridate, d748 1,3-Diphenyl-1,3-propanedione, d68 sym-Diphenylthiourea, t141 Dipicolinic acid, p270 Di-2-propenylamine, d30

⫺117

0.4 aq i aq; s alc, eth v s PE

DEAN 37261 (McGHP)

d781

126 0.5 aq; v s alc, bz, chl, eth, PE s alc, bz, CS2

Dipropyl adipate, d787 Dipropylene glycol, b204 Dipropyl ketone, h16 Distearylpentaerythritol diphosphite, b217 Disulfram, t62

RIGHT ROTATED

d756

d762

d766

d776

d790

INTERACTIVE

No.

Name

d792 d793 d794

1,3-Dithiane 4,4⬘-Dithiobutyric acid 3,3⬘-Dithiodipropionic acid Dithiooxamide 2,2⬘-Dithiosalicylic acid 1,3-Di-o-tolylguanidine Divinyl ether

d795 d796 d797 d798 d799

1.208

d800

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

HO2C(CH2)3SS(CH2)3CO2H HO2C(CH2)2SS(CH2)2CO2H

120.24 238.32 210.27

3, 312

53–55 110 157–159

H2NC(S)C(S)NH2 S2(C6H4CO2H)2

120.20 306.36

2, 565 10, 129

245 287–290

(CH3C6H4NH)2C"NH H2C"CHOCH"CH2

239.32 70.09

1.1020 4 0.77320 4

1.398920

176–178 ⫺101

28.3

⬍ ⫺30

1,3-Divinyltetramethyldisiloxane 3,9-Divinyl-2,4,8,10tetraoxaspiro[5.5]undecane Docasane 1-Docosanol Dodecane 1,12-Dodecanediamine Dodecanedioic acid 1,2-Dodecanediol 1,12-Dodecanediol 1-Dodecanethiol Dodecanoic acid

[CH2 "CHSi(CH3)2]2O

186.39

12, 803 Merck: 12, 10133 4,4,4080

0.81120 4

1.411020

⫺99

139

24

212.25

193, 5679

1.251

43–46

1102mm

110

CH3(CH2)20CH3 CH3(CH2)21OH CH3(CH2)10CH3 H2N(CH2)12NH2 HO2C(CH2)10CO2H CH3(CH2)9CH(OH)CH2OH HOCH2(CH2)10CH2OH CH3(CH2)11SH CH3(CH2)10CO2H

310.61 326.61 170.34 200.37 230.30 202.34 202.34 202.40 200.32

1, 174 1, 431 1, 171 4, 273 2, 729 13, 2237 12, 562

0.778245

1.435845 1.421620

369 18022mm 216.2

⬎110

0.749020 4

43–45 65–72 ⫺10 71 128–130 58–60 81–84

1-Dodecanol ␦-Dodecanolactone Dodecanoyl peroxide 1-Dodecene 2-Dodecen-1-ylsuccinic anhydride Dodecyl acetate Dodecyl acrylate

CH3(CH2)11OH

186.34 198.31 398.63 168.32 266.38 228.38 240.39

[CH3(CH2)10CO]2O2 CH3(CH2)9CH"CH2

CH3CO2(CH2)11CH3 H2C"CHCO2(CH2)11CH3

0.84520 20 0.86914

1.458720 1.418382

1, 428 175,9,100 23, 893 1, 225

0.830825 4 0.942

1.441325 1.460220

0.758420 4

1.429420

2, 136 23, 1230

0.865 0.884

1.431820 1.445020

2, 359

43 24 ⫺12 55–57 ⫺35.2 41–43

Solubility in 100 parts solvent

90

sl s aq; s alc; i eth

s hot alc, eth 0.53 aq; misc alc, eth

i aq; sl s alc; v s eth sl s eth; s alc, chl

74 155

24510mm 18912mm 266–283 225100mm

87 ⬎110

259 1261mm

⬎110 ⬎110

213.4 1805mm

79 177

15015mm

⬎110 ⬎110

i aq; s alc, eth i aq; 100 alc; v s bz, eth; 40 PrOH i aq; s alc, eth

s alc, eth, PE

INTERACTIVE

d815 d816

Beilstein reference

ROTATED

d810 d811 d812 d813 d814

Formula weight

LEFT

d801 d802 d803 d804 d805 d806 d807 d808 d809

Formula

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

CH3(CH2)10CHO CH3(CH2)11NH2 H2C"C(CH3)CO2(CH2)11CH3 CH3(CH2)11SO3⫺ Na⫹

184.32 185.36 254.42 288.38

1, 714 4, 200 23, 1290 13, 1786

0.835 0.808 0.868

d821 d822 d823 d824 e1

Dodecyl aldehyde Dodecylamine Dodecyl methacrylate Dodecyl sulfate, sodium salt Dodecyltrichlorosilane Dodecyl vinyl ether Dotriacontane Dulcitol Eicosane

CH3(CH2)11SiCl3 CH3(CH2)11OCH"CH2 CH3(CH2)30CH3

43, 1907

CH3(CH2)18CH3

303.8 212.38 450.88 182.17 282.56

e2 e3

1R,2S-(⫺)-Ephedrine 1,2-Epoxybutane

CH3NHCH(CH3)CH(OH)C6H5 H2C 9 CHCH2CH3

165.24 72.11

13, 636 172, 17

1.020 0.817 0.812420 4 1.4720 0.7823 (s) 1.124 0.829720

1,177 1, 544 1, 174

1.434420 1.446020

1.45820 1.438220 1.436470

1.385020

30–32 ⫺7 204–207

185100mm 247–249 1424mm

1.209

DMSO, d697 Dodecyl alcohol, d810 Dodecyl iodide, i30 DPPH, d766 Durene, t99 EDTA, e134 Eicosane, i1

⬎110 ⬎110

68–70 188–191 37

294 117–120 467 2801mm 343

39 ⫺150

255 63

85 ⫺22

sl s alc, bz, eth 3.3 aq; sl s alc ⬎110 s aq, alc, chl, eth 6 aq; misc alc, bz, chl, eth

1-Eicosene, i2 Elaidic acid, o11 Enanthic alcohol, h11 Enanthylic acid, h9 Epibromohydrin, b328 Epichlorohydrine, c120 1,4-Epoxybutane, t69

d811

RIGHT

d800

d792

misc alc, bz, chl, eth 10 aq

O

2,3-Dithiabutane, d607 5,6-Dithiadecane, d146 3,4-Dithiahexane, d356 2,2⬘-Dithiodibenzoic acid, d796 2,2⬘-Dithiodiethanol, h123 Dithizone, d773 Divinylene oxide, f45

101 ⬎110 ⬎110

DEAN 37261 (McGHP)

d817 d818 d819 d820

ROTATED

d814

d824

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No. e4

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

178.28

0.980

1.504520

182.31

0.939

1.477320

Melting point,⬚C

Boiling point,⬚C 831mm

Flash point,⬚C

Solubility in 100 parts solvent

⬎110

e6 e7

1,2-Epoxy-5,9-cyclododecadiene 1,2-Epoxycyclododecane 1,2-Epoxycyclopentane 1,2-Epoxydecane

H2C 9 CHCH2(CH2)6CH3

84.12 156.27

17, 21 17, 18

0.964 0.840

1.433620 1.429020

102 9415mm

10 78

e8

1,2-Epoxydodecane

O H2C 9 CHCH2(CH2)8CH3

184.32

173, 136

0.844

1.435520

12515mm

105

1,2-Epoxyethylbenzene

O H2C 9 CHC6H5

120.15

17, 49

1.052316 4

1.533820

⫺37

194

79

1,2-Epoxyhexadecane

O H2C 9 CHCH2(CH2)12CH3

240.43

17, 20

0.846

1.445220

21–22

18012mm

93

1,2-Epoxyhexane

O H2C 9 CHCH2CH2CH2CH3

100.16

174, 86

0.831

1.405620

118–120

15

1,2-Epoxy-5-hexene

O H2C 9 CHCH2CH2CH " CH2

98.15

173, 163

0.870

1.425220

121

15

1,2-Epoxyoctadecane

O H2C 9 CHCH2(CH2)14CH3

268.49

173, 140

33–35

1370.5mm

⬎110

O H2C 9 CHCH2OC6H5

150.18

17, 105

1.109

1.53020

3.5

245

⬎110

⫺112

35

⫺37

41 aq; misc alc, eth misc aq

e5

e9

1.210

e10 e11

e13

e15 e16

1,2-Epoxypropane

O H2C 9 CHCH3

58.08

17, 6

0.85904

1.366020

2,3-Epoxy-1-propanol

O H2C 9 CHCH2OH

74.08

17, 104

1.114325 4

1.431520

662.5mm

81

2,3-Epoxypropylmethacrylate

O H2C 9 CHCH2O2C(CH3)CH " CH2 O

1.042

1.449420

189

76

142.16

INTERACTIVE

e17

1,2-Epoxy-3-phenoxypropane

ROTATED

e14

i aq; s alc, eth

LEFT

e12

⬎110

1,2-Epoxy-3,3,3-trichloropropane

H2C 9 CHCCl3

161.42

172, 14

O HOCH2[CH(OH)]2CH2OH CH3CH3

122.12 30.07

1, 525 1, 80

e19 e20

meso-Erythritol Ethane

e21 e21a e22

H2NCH2CH2NH2 HOCH2CH2OH CH3CO2CH2CH2O2CCH3

60.10 62.07 146.14

[H2C"C(CH3)CO2CH⫺2 ]2 HSCH2CH2SH C2H5SO3H CH3CH2SO2Cl

e26a e27 e28 e29

1,2-Ethanediamine 1,2-Ethanediol 1,2-Ethanediol diacetate 1,2-Ethanediol dimethacrylate 1,2-Ethanedithiol Ethanesulfonic acid Ethanesulfonyl chloride Ethanethiol Ethanol Ethanol-d Ethanolamine

e30

Ethoxyacetic acid

CH3CH2OCH2CO2H

e23 e24 e25 e26

1.211

CH3CH2SH CH3CH2OH CH3CH2OD H2NCH2CH2OH

1.477820

4, 230 1, 465 2, 142

1.3560 g/L 0.897720 4 1.113520 4 1.104320

1.456820 1.431820 1.415020

198.22

23, 1292

1.051

1.454920

94.20 110.13 128.57

1, 471 4, 5 4, 6

1.12324 1.350 1.35722

1.558020 1.434020 1.433020

1, 340 1, 292 13, 1287 Merck: 12, 3712 3, 233

0.831525 0.789420 4 0.801 1.018020

1.42025 1.361120 1.359520 1.453920

1.102120 4

1.419020

62.13 46.07 47.08 61.08 104.11

Ethanedial, g28 1,2-Ethanediol, e135 Ethanediamide, o58 Ethanenitrile, a29 Ethanoic acid, a19 Ethanoic anhydride, a22 Ethanolamine, a164

151745mm

66

120–123 ⫺182.8

329–331 ⫺88

⫺135

4.7 mL aq; 46 mL alc4

11 ⫺12.6 ⫺31

117.3 197.3 190.2

33 110 82

misc aq, alc; i bz misc aq, alc, glyc, pyr misc alc, eth

1005mm

⬎110

146 1230.01mm 177

50 ⬎110 83

v s alc, alk

35.0 78.3 78.8 170.8

⫺17 13 12 86

0.7 aq; s alc, eth misc aq, alc, chl, eth misc aq, alc, eth misc aq, alc, acet

9711mm

97

s aq, alc, eth

⫺17

⫺147.9 ⫺114 10.5

Ethanoyl bromide, a35 Ethanoyl chloride, a37 Ethene, e131 Ethenone, k1 Ethenyl acetate, v2 Ethenylbenzene, s11

dec aq, alc; v s eth

RIGHT

Epoxyethane, e147 1,2-Epoxy-1-methoxy-2-methylpropane, m86 1,2-Epoxypropane, p232 Estragole, a89 Ethanal, a4 Ethanamide, a6 Ethanamidine HCl, a7

1.495

DEAN 37261 (McGHP)

e18

ROTATED

e4

e5

e6

INTERACTIVE

No. e31 e32 e33 e34 e35 e36 e37 e38 e39 e40 e41

1.212

e41a

e46 e47

e49 e50 e51 e52

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

C2H5OCH"CHCN CH3CH2OC6H5NH2 CH3CH2OC6H4CHO CH3CH2OC6H4CHO CH3CH2OC6H4CONH2 CH3CH2OC6H5 CH3CH2OC6H4CO2H CH3CH2OC6H4CO2H CH3CH2OC("O)NCS

97.12 137.18 150.18 150.18 165.19 122.17 166.18 166.18 131.15

33, 681 13, 436 8, 43 8, 73 10, 93 6, 140 10, 64 10, 156 33, 279

0.944 1.065216 4 1.074 1.08025 25

1.454520 1.560920 1.5422 1.558420

0.96720 4 1.105

1.507420 1.540020

1.112

1.500020

CH3CH2OCH2CH2OH C2H5OCH2CH2OCH2CH2OH

90.12 134.18

1, 467 12, 520

0.929520 0.984125 4

1.407520 1.425425

CH3CO2CH2CH2OCH2CH2OCH2CH3 CH3CO2CH2CH2OCH2CH3 H2C"CHCO2CH2CH2OC2H5 CH3CH2OCH2CH2NH2 H2C"C(CH3)CO2CH2CH2OC2H5

176.21

1.009620

132.16 144.17 89.14 158.20

22, 23, 42, 23,

0.974920 4 0.982 0.851220 4 0.964

C2H5OC6H3(OH)CHO

166.18

8, 256

76–78

C2H5OC6H3(OCH3)CHO

180.2

8, 256

51–53

C2H5OC6H4OCH3

152.19

6, 771

155 1232 718 1291

1.044

Flash point,⬚C

9119mm 250 13624mm 255

81 115 107 ⬎110

169.8 17415mm

63 ⬎110

5618mm

50

⫺70 ⫺76

134.8 196

43 96

1.421320

⫺25

218.5

110

1.402320 1.427020 1.410120 1.428520

⫺61.7

156.3 7823mm 107 9335mm

57 65 21 71

4 20 13–14 132–134 ⫺29.5 19.4 197–199

1.524020

1

CH3CH2OCH"C(CN)2

122.13

3 , 162

C10H7OCH2CH3 C2H5OC6H4OH C2H5OC6H3(CH"CHCH3)OH

172.23 138.17 178.23

6, 606 6, 771 62, 918

1.06020 4 1.090

1.604020 1.528820

99.14

3, 298

0.911

1.406520

C2H5OCH2CH2CN

Boiling point,⬚C

Solubility in 100 parts solvent

i aq; s alc misc alc, eth v s alc, bz, eth sl s aq; s alc, eth v s alc, eth sl s aq sl s hot aq

misc aq, alc, acet, eth misc aq, alc, bz, chl, acet, pyr

29 aq; misc alc, eth misc aq, alc, eth

s eth, glycols; 50 alc ⬎110 217–218

s alc, bz, chl, eth

90

12mm

64–66

160

5.5 29 86–88

280 217

⬎110 91

171–172

63

i aq; v s alc, eth

INTERACTIVE

e53

Formula weight

ROTATED

e48

3-Ethoxyacrylonitrile 4-Ethoxyaniline 2-Ethoxybenzaldehyde 4-Ethoxybenzaldehyde 2-Ethoxybenzamide Ethoxybenzene 2-Ethoxybenzoic acid 4-Ethoxybenzoic acid Ethoxycarbonyl isothiocyanate 2-Ethoxyethanol 2-(2-Ethoxyethoxy)ethanol 2-(2-Ethoxyethoxy)ethanol acetate 2-Ethoxyethyl acetate 2-Ethoxyethyl acrylate 2-Ethoxyethylamine 2-Ethoxyethyl methacrylate 3-Ethoxy-4-hydroxybenzaldehyde 3-Ethoxy-4-methoxybenzaldehyde 1-Ethoxy-2-methoxybenzene Ethoxymethylenemalononitrile 1-Ethoxynaphthalene 2-Ethoxyphenol trans-2-Ethoxy-5-(1propenyl)phenyl 3-Ethoxypropionitrile

Formula

LEFT

e42 e43 e44 e45

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

e56 e57 e58 e59 e60 e61 e62 e63 e64 e65 e66

1.213

e67 e68 e69 e70 e71 e72 e73

3-Ethoxypropylamine 3-Ethoxysalicylaldehyde Ethoxytrimethylsilane Ethyl acetate

C2H5OCH2CH2CH2NH2 C2H5OC6H3(OH)CHO

103.17 166.18

43, 739 82, 267

0.861

(CH3)3SiOC2H5 CH3CO2C2H5

118.3 88.11

43, 1856 2, 125

0.757320 4 0.900620 4

1.374220 1.372420

Ethyl acetoacetate p-Ethylacetophenone Ethyl acrylate Ethylaluminum dichloride Ethylaluminum sesquichloride Ethylamine Ethyl 2-aminobenzoate Ethyl 4-aminobenzoate

CH3COCH2CO2C2H5 C2H5C6H4COCH3 H2C"CHCO2C2H5 C2H5AlCl2

130.15 148.21 100.12 126.95

3, 632 74, 1101 2, 399 43, 1973

1.021325 4 0.993 0.923420 1.20750

1.417420 1.529320 1.406020

C2H5AlCl2 · ClAl(C2H5)2

247.51

C2H5NH2 H2NC6H4CO2C2H5 H2NC6H4CO2C2H5

45.09 165.19 165.19

4, 87 14, 319 14, 422

0.68915 15 1.08815

Ethyl 3-aminocrotonate 2-(Ethylamino)ethanol N-Ethylaniline 2-Ethylaniline 4-Ethylaniline 2-Ethylanthraquinone 4-Ethylbenzaldehyde Ethylbenzene-d10

CH3C(NH2)"CHCO2C2H5

129.16

3, 654

1.02120 4

CH3CH2NHCH2CH2OH C6H5NHC2H5 CH3CH2C6H4NH2 CH3CH2C6H4NH2

89.14 121.18 121.18 121.18 236.27 134.18 116.25

4, 282 12, 159 122, 584 12, 1090 71, 425 7, 307

0.91420 4 0.95825 25 0.983 0.975

1.440220 1.555920 1.559020 1.554220

0.979 0.949

1.539020 1.492020

1.092

(Ethoxymethyl)benzene, b97 ␣-Ethoxy-␣-phenylacetophenone, b47 3-Ethoxy-1-propene, a86 Ethylacetylene, b160a

1.366320 1.564020

136–138 264

32

66–68

⫺84

75–76 77

⫺18 ⫺4

⫺45 ⫺20.6 ⫺71 32

180.8 11411mm 99 11350mm

57 90 10 ⫺18

⫺50

204

⫺18

⫺81 13–15 88–90

16.6 266–268 310

⬍ ⫺18 ⬎110

33–35

210–215

97

misc aq, alc, eth i aq; s alc, eth 0.04 aq; 20 alc; 50 chl, 25 eth; s dil acid i aq; s alc, bz, eth

⫺90 ⫺63.5 ⫺44 ⫺5 108–111

170 203 210 216

71 85 91 85

v s aq, alc, eth i aq; misc alc, eth sl s aq; v s alc, eth sl s aq; v s alc, eth

221 134.6

92 31

Ethyl alcohol, e27, e28 Ethylaldehyde, a4 Ethyl anthranilate, e64 Ethyl benzencarboxylate, e76

9.7 aq; misc alc, acet, chl, eth 2.9 aq; misc alc, chl 1.5 aq; s alc, eth

RIGHT ROTATED

4-Ethoxy-m-anisaldehyde, e48 1-Ethoxybutane, b554 Ethoxyethane, d365 2-Ethoxyethyl ether, b186 Ethoxyformic anhydride, d386

C2H5C6H4CHO C6D5CD2CD3

1.417820

DEAN 37261 (McGHP)

e54 e55

e71

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

106.17

52, 274

0.867020 4

1.495920

e75

4-Ethylbenzenesulfonic acid Ethyl benzoate

C2H5C6H4SO3H

186.23

11, 120

1.229

1.5331

C6H5CO2C2H5

150.18

9, 110

1.05115

1.500020

Ethyl benzoylacetate Ethyl 3-benzoylacrylate Ethyl 2-benzylacetoacetate N-Ethylbenzylamine Ethyl (2-benzyl)benzoylacetate Ethyl N-benzyl-Ncyclopropylcarbamate Ethyl bromoacetate Ethyl 4-bromobenzoate Ethyl 2-bromobutyrate Ethyl 4-bromobutyrate Ethyl 2-bromoheptanoate Ethyl 6-bromohexanoate Ethyl 2-bromoisobutyrate Ethyl 2-bromooctanoate Ethyl 3-bromo-2-oxopropionate

C6H5(C"O)CH2CO2C2H5 C6H5(C"O)CH"CHCO2C2H5

192.21 204.23

10, 674 102, 501

1.110 1.112

CH3C("O)CH(CH2C6H5)CO2C2H5

220.27

10, 710

C6H5CH2NHC2H5 C6H5C("O)CH(CH2C6H5)CO2C2H5 C6H5CH2N(C3H5)CO2C2H5

135.21 282.34

12, 1020 10, 764

BrCH2CO2CH2CH3 BrC6H4CO2C2H5

167.01 229.08

CH3CH2CH(Br)CO2C2H5 BrCH2CH2CH2CO2C2H5 CH3(CH2)3CH(Br)CO2C2H5

e76 e77 e78 e79

1.214

e80 e81 e82

e83 e84 e85 e86 e87 e88 e89 e90 e91

⫺95.0

136.2

22

0.01 aq; misc alc, bz, chl, eth

⬎110 ⫺34.7

212.4

84

1.533820 1.543520

265–270 18525mm

63 ⬎110

1.036

1.499620

276

⬎110

0.909 1.110

1.511720 1.556720

194 27080mm

66 ⬎110

0.997

1.510420

2, 214 9, 352

1.50620 20 1.403

1.451020 1.544020

195.06 195.06 237.14

22, 255 2, 283 2, 341

1.32920 20 1.363 1.211

Br(CH2)5CO2C2H5

223.12

23, 737

(CH3)2C(Br)CO2C2H5

195.06

CH3(CH2)5CH(Br)CO2C2H5 BrCH2C("O)CO2C2H5

219.28

Solubility in 100 parts solvent

0.05 aq; misc alc, chl, bz, eth, PE i aq; misc alc, eth

⬎110

⬍ ⫺20

159 13114mm

47 ⬎110

i aq; misc alc, eth

1.447020 1.455920 1.452420

177 dec 8210mm 10910mm

58 90 104

i aq; misc alc, eth

1.254

1.459020

13016mm

⬎110

2, 296

1.32920 4

1.444620

6711mm

60

251.17

2, 349

1.167

1.452020

195.02

32, 409

1.554

1.469520

i aq; misc alc, eth

106 10010mm

98

INTERACTIVE

C6H5CH2CH3

Flash point,⬚C

ROTATED

Ethylbenzene

Boiling point,⬚C

LEFT

e74

Melting point,⬚C

e95 e95a e96 e97 e98 e99 e100 e101

Ethyl 2-bromopentanoate Ethyl 2-bromopropionate Ethyl 3-bromopropionate 2-Ethyl-1-butanol 2-Ethyl-1-butene 2-Ethylbutyl acetate N-Ethylbutylamine 2-Ethylbutyraldehyde Ethyl butyrate 2-Ethylbutyric acid Ethyl butyrylacetate

e102

Ethyl carbamate

e103 e104 e105 e106

Ethyl carbazate N-Ethylcarbazole Ethyl chloroacetate Ethyl 2-chloroacetoacetate Ethyl 4-chloroacetoacetate

e93 e94

1.215

e107

CH3(CH2)2CH(Br)CO2C2H5

209.09

2, 302

1.116

1.448620

190–192

77

i aq; misc alc, eth

CH3CH(Br)CO2C2H5

181.03

2, 255

1.394

1.446020

156–160

51

i aq; misc alc, eth

136

79

i aq; misc alc, eth

146 65 160740mm 108 116.7 121 194 10422mm

58 ⫺26 52 18 21 24 87 78

0.63 aq

49–50

182–184

92

200 aq; 125 alc; 111 chl; 67 eth

44–47 68–70 ⫺21

11022mm

86

144 10714mm

65 50

i aq; misc alc, eth i aq; s alc, eth

11514mm

96

i aq; misc alc, eth

18 4

18

BrCH2CH2CO2C2H5

181.03

2, 256

1.4123

1.4569

(C2H5)2CHCH2OH (C2H5)2C"CH2 CH3CO2CH2CH(C2H5)2 CH3(CH2)3NHC2H5 (C2H5)2CHCHO CH3CH2CH2CO2C2H5 (C2H5)2CHCO2H CH3(CH2)2C("O)CH2CO2C2H5 H2NCO2C2H5

102.18 84.16 144.21 101.19 100.16 116.16 116.16 158.20

1, 412 12, 95 23, 257 4, 157 1, 693 2, 270 2, 333 3, 684

0.833020 0.689 0.876 0.74020 4 0.816220 20 0.87920 4 0.922520 20 1.001

1.422420 1.396020 1.410020 1.405020 1.401820 1.399820 1.413320 1.427020

3, 22

1.056

H2NNHCO2C2H5 ClCH2CO2C2H5 CH3C("O)CH(Cl)CO2C2H5

104.11 195.27 122.55 164.59

3, 98 20, 436 2, 197 3, 662

1.149820 4 1.190

1.422720 1.443020

ClCH2C("O)CH2CO2C2H5

164.59

3, 663

1.21817 4

1.452020

Ethyl bromopyruvate, e91 Ethyl bromovalerate, e92 Ethyl butanoate, e99 2-Ethylbutyl alcohol, e95 Ethyl butyl ether, b554

⬍ ⫺15 ⫺131

⫺89 ⫺98 ⫺14

Ethyl butyl ketone, h15 Ethyl caprate, e120 Ethyl caproate, e160 Ethyl caprylate, e231 Ethyl chloride, c121

0.31 aq 0.49 aq; misc alc, eth

RIGHT

Ethyl 3-benzenepropenoate, e113 ␣-Ethylbenzyl alcohol, p145 Ethyl benzyl ether, b97 Ethyl bromide, b329 Ethyl 2-bromo-2-methylpropanoate, e89

89.09

50mm

DEAN 37261 (McGHP)

e92

ROTATED

e104

INTERACTIVE

Ethyl 4-chlorobutyrate Ethyl chloroformate Ethyl 2-chloropropionate Ethyl 3-chloropropionate Ethyl chrysanthemumate Ethyl trans-cinnamate Ethyl crotonate Ethyl cyanoacetate Ethyl 2-cyano-3,3diphenylacrylate Ethylcyclohexane 4-Ethylcyclohexanol Ethylcyclopentane Ethyl cyclopropanecarboxylate Ethyl decanoate Ethyl diazoacetate Ethyl 2,3-dibromopropionate Ethyl dichlorophosphate Ethyl dichlorothiophosphate N-Ethyldiethanolamine Ethyl 3,3-dimethylacrylate Ethyl 4-dimethylaminobenzoate Ethyl 2,2-dimethylpropionate

e111 e112 e113 e114 e115 e116

1.216

e117 e118 e118a e119 e120 e121 e122 e123 e124 e125 e126 e127 e128

Formula weight

Beilstein reference

Density, g/mL

Refractive index

ClCH2CH2CH2CO2C2H5 ClCO2C2H5 CH3CH(Cl)CO2C2H5

150.61 108.52 136.58

2, 278 3, 10 2, 248

1.075420 4 1.140320 4 1.08720 4

1.430620 1.394120 1.418520

ClCH2CH2CO2C2H5

136.58

2, 250

1.108620 4

196.29

92, 45

C6H5CH"CHCO2C2H5 CH3CH"CHCO2C2H5 NCCH2CO2C2H5 (C6H5)2C"C(CN)CO2C2H5

176.22 114.14 113.12 277.33

C6H11CH2CH3 CH3CH2C6H10OH C2H5(C5H9) C3H5CO2CH2CH3

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

186 93 38

51 13

s alc, acet, eth misc alc, bz, chl, eth

1.424920

162–163

54

misc alc, eth

0.906

1.460020

11210mm

84

92, 385 2, 411 2, 585 93, 4601

1.049520 4 0.917520 4 1.056425 4

1.559820 1.424020 1.417620

10

271 138 206 1740.2mm

⬎110 28 110

112.22 128.22 98.19 114.14

5, 35 62, 26 52, 19 9, 4

0.787920 0.889 0.763 0.960

1.433020 1.462520 1.419020 1.419720

⫺111

131.8 8410mm 103 129–133

35 77 15 18

CH3(CH2)8CO2C2H5 N2CH2CO2C2H5 BrCH2CH(Br)CO2C2H5

200.32 114.10 259.94

2, 356 31, 211 2, 259

0.86220 1.085218 4 1.78816 4

1.424820 1.458818 1.498620

245 141710mm 214

102 26 91

CH3CH2OP(O)Cl2

162.94

1, 332

1.373

1.433820

6510mm

⬎110

CH3CH2OP(S)Cl2

179.01

1, 353

1.353

1.504020

6810mm

⬎110

246–252 155

123 33

118.2

16

CH3CH2N(CH2CH2OH)2 (CH3)2C"CHCO2C2H5

133.19 128.17

4, 284 2, 433

(CH3)2NC6H4CO2C2H5

193.25

141, 571

(CH3)3CCO2C2H5

130.19

2, 320

1.014 0.924720 4

20

1.4665 1.435020

⫺81 146–149

⫺22 97–99

⫺138

⫺22

⫺50

misc alc, eth; i aq i aq; s alc, eth i aq; misc alc, eth

misc alc, chl, eth misc alc, bz, eth s alc, eth

64–66 0.858418 4

1.392218

s alc, eth

INTERACTIVE

e108 e109 e110

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

e130 e131 e132 e133 e134

e135 e136 e137 e138

1.217

e139 e140

Ethyl 3,5-dinitrobenzoate 5-Ethyl-1,3-dioxane5-methanol Ethylene Ethylene carbonate Ethylenediamine EthylenediamineN,N,N⬘,N⬘-tetraacetic acid Ethylene glycol Ethylene glycol bis(mercaptoacetate) Ethylene glycol diacetate Ethylene glycol diethyl ether Ethylene glycol diglycidyl ether Ethylene glycol dimethacrylate

240.17

9, 414

146.19

195,2,382

1.090

1, 180

1.147 g/L

88.06 60.10 292.24

19, 100 4, 230 43, 1187

1.321439 0.87920

HOCH2CH2OH (HSCH2CO2CH2 9)2

62.07 210.27

1, 465

1.113 1.313

1.431020 1.521120

CH3CO2CH2CH2O2CCH3

146.14

2, 142

1.104320

1.415920

C2H5OCH2CH2OC2H5

118.18

1, 468

0.848420

(H2C 9 CHCH2OCH2⫺)2

174.20

1, 468

O [H2C"C(CH3)CO2CH2⫺]2

198.22

23, 1292

H2C"CH2

28.05

H2NCH2CH2NH2 (HO2CCH2)2NCH2CH2N(CH2CO2H)2

94–95 1.463020

1.419940 1.456620

1055mm ⫺169.4

⫺104

36.4 11 250 dec

248 117

⬎110

143 40

0.05 aq

196–198 1392mm

⬎110 ⬎110

⫺31

190

88

1.386020

⫺74

119

35

0.842

1.392320

⫺74

121

20

1.051

1.454920

1005mm

⬎110

Ethylene cyanohydrin, h173 Ethylene diacetate, e22 Ethylenediamine, e21 Ethylene dibromide, d97 Ethylene dichloride, d226 Ethylene diglyme, b186 (Ethylenedinitril)tetraacetic acid, e134 2,2⬘-Ethylenedioxybis(ethanol), t280

11 mL aq25; 200 alc25; v s eth; s acet, bz misc aq

Ethylene glycol, e21a Ethylene glycol bis(thioglycolate), e136 Ethylene glycol tert-butyl ether, b494 Ethylene glycol tert-butyl methyl ether, b498 Ethylene glycol p-butylphenyl ether, b590 Ethylene glycol diacetate, e22 Ethylene glycol diethyl ether, d304 Ethylene glycol dimethacrylate, e23

RIGHT

Ethyl chloroglyoxylate, e232 Ethyl citrate, t278 Ethyl cyanide, p215 Ethyl 2-cyano-3-ethoxyacrylate, e150 N-Ethyldiisopropylamine, d477 Ethylene bromohydrin, b331 Ethylene chlorobromide, b303 Ethylene chlorohydrin, c122

(O2N)2C6H3CO2C2H5

DEAN 37261 (McGHP)

e129

ROTATED

e112

e130

e132

INTERACTIVE

No.

Name

e141

Ethylene glycol dimethyl ether Ethylene glycol divinyl ether Ethylene glycol methyl ether acrylate Ethylene glycol methyl ether methacrylate Ethylene glycol phenyl ether acrylate Ethyleneimine

e142 e143 e144 e145 e146

Formula CH3OCH2CH2OCH3

1.379620

⫺58

Flash point,⬚C

85

⫺2

Solubility in 100 parts solvent

1.218

125–127

27

H2C"CHCO2CH2CH2OCH3

130.14

23, 1232

1.012

1.427020

5612mm

60

H2C"C(CH3)CO2CH2CH2OCH3

144.17

23, 1291

0.993

1.431020

6512mm

60

H2C"CHCO2CH2CH2OC6H5

192.21

63, 572

1.104

1.518020

840.2mm

⬎110

0.832125 4

1.412325

⫺78

56

⫺11

misc aq; s alc

⫺111

10.6

⫺18

misc aq; s alc, eth sl s alc, eth

17, 4

0.89104

1.35977

60.12

172, 12

1.010

1.493520

55–56

10

S HOCH(OC2H5)CO2C2H5

148.16

3, 601

1.079

1.420020

137

49

C2H5OCH"C(CN)CO2C2H5

169.18

3, 470

19030mm

⬎110

C2H5OCH2CH2CO2C2H5

146.19

3, 298

166

52

C6H5N(C2H5)CH"N9C6H4CO2C2H5

296.37

FCH2CO2C2H5 HCO2C2H5

106.10 74.08 140.14 158.24

CH3(CH2)5CO2C2H5

2, 193 2, 19 18, 275 22, 295

51–53

0.949

1.092621 0.91720 4 1.11720 4 0.868520 4

1.405020

1.375520 1.359020 1.414415

62–65

2152mm

⫺80 35–37 ⫺66

119 54 196 189

30 ⫺20 70 66

s aq 10 aq; misc alc, eth i aq; s alc, eth s alc, eth

INTERACTIVE

44.05

ROTATED

43.07

LEFT

H2C 9 CH2

O H2C 9 CH2

e153 e154 e155 e156

0.869120

Boiling point,⬚C

1.435020

Ethylene sulfide

e152

1, 467

Melting point,⬚C

0.914

e148

e151

Refractive index

13, 2807

Ethylene oxide

e150

Density, g/mL

114.14

e147

Ethyl 2-ethoxy-2hydroxyacetate Ethyl (ethoxymethylene)cyanoacetate Ethyl 3-ethoxypropionate Ethyl 4-{[(ethylphenylamino)methylene]amino}benzoate Ethyl fluoroacetate Ethyl formate Ethyl 2-furoate Ethyl heptanoate

90.12

Beilstein reference

H2C"CHOCH2CH2OCH"CH2

N H H2C 9 CH2

e149

Formula weight

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Ethyl hexadecanoate 2-Ethylhexanaldehyde 3-Ethylhexane 2-Ethyl-1,3-hexanediol

e160 e161 e162

Ethyl hexanoate 2-Ethylhexanoic acid 2-Ethyl-1-hexanol

e163

2-Ethylhexanoyl chloride 2-Ethylhexyl acetate

e164 e165 e166 e167 e168

1.219

e169

2-Ethylhexyl acrylate 2-Ethylhexylamine 2-Ethylhexyl chloroformate 2-Ethylhexyl cyanoacetate 2-Ethylhexyl 2-cyano3,3-diphenylacrylate

22, 336 1, 707 14, 431 Merck: 12, 3790 2, 323 2, 349 Merck: 12, 3854 22, 304

0.857725 4 0.822 0.713620 0.932522 4

1.434734 1.4155 1.401820 1.453022

22

⫺40

19110mm 5513.5mm 118.6 244

0.87120 4 0.9077 0.831925

1.407520 1.424120 1.430020

⫺67 ⫺118.4 ⫺70

166–168 228 184.6

49 127 73

0.939

1.433520

6811mm

69

Merck: 12, 6860 23, 1229 43, 388 34, 28

0.8718

1.420420

⫺80

199

71

0.885 0.789 0.981

1.4358 1.430020 1.431220

⫺76

214–219 169 10730mm

79 60 81

197.28

0.975

1.438020

15011mm

⬎110

361.49

1.051

1.567020

2181.5mm

⬎110

CH3(CH2)14CO2C2H5 CH3(CH2)3CH(C2H5)CHO (C2H5)CHCH2CH2CH3 CH3(CH2)2CH(OH)CH(C2H5)CH2OH CH3(CH2)4CO2C2H5 CH3(CH2)3CH(C2H5)CO2H CH3(CH2)3CH(C2H5)CH2OH

144.21 144.21 130.23

CH3(CH2)3CH(C2H5)COCl

162.66

CH3(CH2)3CH(C2H5)CH2O2CCH3 H2C"CCO2CH(C2H5)(CH2)3CH3 CH3(CH2)3CH(C2H5)CH2NH2 CH3(CH2)3CH(C2H5)CH2O2CCl

172.27

NCCH2CO2CH2CH(C2H5)(CH2)3CH3 (C6H5)2C"C(CN)CO2CH2CH(C2H5)(CH2)3CH3

184.28 129.31 192.69

Ethylene glycol monomethyl ether acetate, m75 Ethylene iodide, d451 Ethylene iodohydrin, i32 1,8-Ethylenenaphthalene, a2 Ethylenethiourea, i4 Ethylene trichloride, t232 Ethyleneurea, i5

⫺10

s alc, eth 42 127

N-Ethylethanamine, d323 Ethyl 2-ethoxyglycolate, e149 Ethyl N-ethylcarbamate, e275 Ethyl fluoride, f17 2-Ethyl-1-hexanamine, e166 2-Ethylhexyl alcohol, e162

s alc, eth 0.6% (w/w) aq; s alc, propylene glycol i aq; misc alc, eth 0.25 aq 0.07 aq; s alc, bz, chl

0.03 aq; misc alc, oils, org liquids i aq; s alc, acet, eth

RIGHT

Ethylene glycol dimethyl ether, d505 Ethylene glycol ethyl ether acetate, e42 Ethylene glycol monoacetate, h120 Ethylene glycol monobutyl ether, b493 Ethylene glycol monobutyl ether acetate, b497 Ethylene glycol monoethyl ether, e40 Ethylene glycol monomethyl ether, m71

284.48 128.22 114.23 146.23

DEAN 37261 (McGHP)

e157 e158 e158a e159

ROTATED

e155

INTERACTIVE

No. e170

e171

e172 e173 e174 e175

1.220

e176 e177 e178

e180 e181

e183

e184

2-Ethylhexyl methacrylate 2-Ethylhexyl nitrate 2-Ethylhexyl salicylate

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

(CH3)2NC6H4CO2CH2CH(C2H5)(CH2)3CH3

277.41

0.995

1.542020

325

⬎110

CH3(CH2)3CH(C2H5)CH2OCH2CH 9CH2

186.30

0.891

1.434020

610.3mm

96

O H2C"C(CH3)CO2CH2CH(C2H5)(CH2)3CH3 CH3(CH2)3CH(C2H5)CH2ONO2 2-(HO)C6H4CO2CH2CH(C2H5)(CH2)3CH3 CH3(CH2)3CH(C2H5)CH2OCH"CH2 C6H5CH2CH2CO2C2H5 HO2C(CH2)4CO2C2H5

Solubility in 100 parts solvent

198.31

23, 1289

0.885

1.438120

12018mm

92

175.23 250.34

0.963 1.014

1.432020 1.502020

19021mm

75 ⬎110

explodes when heated

103, 124

0.8102

1.427320

⫺85

177–178

52

0.01 aq

1.010

1.494020 1.438720

28–29

247–248 18018mm

107 ⬎110

116–118

297–298

156.26 178.23 174.20

9, 511 21, 277

HOC6H4CO2C2H5

166.18

10, 159

CH3CH(OH)CH2CO2C2H5

132.16

3, 309

1.01720 4

1.420520

170

64

s aq, alc

HOCH2CH2SCH2CH3

106.19

12, 525

1.020

1.486920

180–184

⬎110

s eth

HO(CH2)5CO2C2H5

160.22

3,3,628

0.985

1.437020

12812mm

⬎110

(CH3)2C(OH)CO2C2H5

132.16

3, 315

0.965

1.407820

150

44

C2H5C(CH2OH)3

134.18

(H2C"CHCO2CH2)3CC2H5

296.32

3

1 , 2349

60–62

1.100

1.473620

0.07 aq; v s alc, eth

2mm

161

157

⬎110

dec by hot aq

INTERACTIVE

2-Ethylhexyl vinyl ether Ethyl hydrocinnamate Ethyl hydrogen hexanedioate Ethyl 4-hydroxybenzoate Ethyl 3-hydroxybutyrate Ethyl 2-hydroxyethyl sulfide Ethyl 6-hydroxyhexanoate Ethyl 2-hydroxyisobutyrate 2-Ethyl-2-(hydroxymethyl)-1,3propanediol 2-Ethyl-2-(hydroxymethyl)-1,3propanedioltriacrylate

Formula weight

ROTATED

e182

2-Ethylhexyl 4-(dimethylamino)benzoate 2-Ethylhexyl glycidyl ether

Formula

LEFT

e179

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

e186 e187

e188

e189 e190

1.221

e191 e192 e193

2-Ethyl-2-(hydroxymethyl)-1,3propanedioltrimethacrylate N-Ethyl-3-hydroxypiperidine 2,2⬘-Ethylidenebis(4,6-di-tert-butylphenol) 2,2⬘-Ethylidenebis(4,6-di-tert-butylphenyl) fluorophosphite 4,4⬘-Ethylidenebisphenol 5-Ethylidene-2norborene 2-Ethylimidazole Ethyl isobutyrate Ethyl isothiocyanate

[H2C"C(CH3)CO2CH2]3CC2H5

338.40

129.20 CH3CH{C6H2[C(CH3)3]2OH}2

CH3CH2CH(C6H4OH)2

Merck: 12, 3890

0.970

1.475420

⬎110

9515mm 162–164

486.66

201–203

214.26

6, 1006

96.13 116.16 87.14

23, 78 2, 291 4, 123

47

123–127 0.893

1.4895

0.87020 1.00318 4

1.390320 1.514218

Ethylidene chloride, d225 Ethylidene dimethyl ether, d504 Ethylidene fluoride, d407 2,2⬘-Ethyliminodiethanol, e125 Ethyl iodide, i31

38 86 ⫺88 ⫺6

268 110 130–132

13 32

misc alc, eth; sl s aq i aq; misc alc, eth

Ethyl isopentanoate, e208 Ethyl isonipicotate, e250 Ethyl isopropylactate, e208 Ethyl isothiocyanatoformate, e39 Ethyl isovalerate, e208

RIGHT

Ethyl hexyl ketone, n100 Ethyl hydrogen adipate, e177 N-Ethyl-N-(2-hydroxyethyl)-3-toluidine, e267 Ethyl 2-hydroxy-2-methylpropanoate, e182 Ethyl 2-hydroxypropionate, e194 Ethylidene bromide, d96

1.472420

438.70

120.20

(CH3)2CHCO2C2H5 CH3CH2NCS

1.060

DEAN 37261 (McGHP)

e185

ROTATED

e186

e188

e190

e191

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

118.13

3, 264

1.032820

1.412420

⫺26

154–155

46

e195 e196

Ethyl (⫾)-mandelate Ethyl 2-mercaptoacetate Ethyl 3-mercaptopropionate Ethylmercury chloride Ethyl methacrylate Ethyl 4-methoxyphenylacetate Ethyl 2-methylacetoacetate N-Ethyl-2-methylallylamine N-Ethyl-N-methylaniline Ethyl 2-methylbenzoate Ethyl 3-methylbenzoate Ethyl 4-methylbenzoate Ethyl 2-methylbutyrate Ethyl 3-methylbutyrate 2-Ethyl-2-methyl-1,3dioxolane Ethyl methyl ether

C6H5CH(OH)CO2C2H5 HSCH2CO2C2H5

180.21 120.17

10, 202 3, 255

1.115 1.0964

1.512020 1.457120

33–34

253–255 5412mm

⬎110 47

HSCH2CH2CO2C2H5

134.20

33, 555

1.039

1.457020

7610mm

72

CH3CH2HgCl H2C"C(CH3)CO2C2H5 CH3OC6H4CO2C2H5

165.13 114.14 194.23

2, 423 101, 83

3.5 0.917 1.097

1.411625 1.507520

sublimes 118 1387mm

15 46

CH3C("O)CH(CH3)CO2C2H5

144.17

3, 679

1.019

1.428020

187

62

99.18

44, 1104

0.753

1.422120

105

7

C6H5N(CH3)C2H5

135.21

12, 162

0.947

1.547020

203–205

74

CH3C6H4CO2C2H5

164.21

9, 463

1.032

1.507020

221731mm

91

CH3C6H4CO2C2H5

164.21

9, 476

1.030

1.505420

11020mm

101

20

235

99

⫺99

133 135 116–117

26 26 12

⫺113

7.4

e197

1.222

e198 e199 e200 e201 e202 e203 e204 e205 e206 e207 e208 e209 e210

H2C"C(CH3)CH2NHC2H5

192

CH3C6H4CO2C2H5

164.21

9, 484

1.025

1.5085

CH3CH2CH(CH3)CO2C2H5 (CH3)2CHCH2CO2C2H5

130.19 130.19 116.16

2, 305 22, 275 192, 11

0.869 0.865620 0.929

1.396920 1.396220 1.409020

60.10

1, 314

2.456 g/L

C2H5OCH3

misc aq, alc, eth, esters, PE s alc, eth

0.78 eth; 2.6 chl i aq; s alc, eth

i aq; s alc, eth

i aq; misc alc, eth

0.2 aq; misc alc, bz

s aq; misc alc, eth

INTERACTIVE

CH3CH(OH)CO2C2H5

ROTATED

Ethyl (⫺)-lactate

LEFT

e194

Solubility in 100 parts solvent

e211 e212

e213

e214 e215 e216

e217

1.223

3-Ethyl-4-methylhexane 2-Ethyl-4-methylimidazole Ethyl 4-methyl-5imidazolecarboxylate 4-Ethyl-2-methyl-2(3-methylbutyl)oxazolidine 3-Ethyl-2-methylpentane 3-Ethyl-3-methylpentane Ethyl 1-methyl-2piperidinecarboxylate Ethyl 1-methyl-3piperidinecarboxylate

(C2H5)2CHCH(CH3)C2H5

128.26 110.16 154.17

232, 72

114.24

(C2H5)3CCH3

114.24 171.24

0.975

1.500020

25 , 534

13, 489

221, 485

171.24

Ethyl levulinate, e236 Ethyl linoleate, e229 Ethyl mercaptan, e26a

1.413420

1

185.3

(C2H5)2CHCH(CH3)2

0.742020

47–54

140

24

292–295

137

194

82

⬍21

204–206

0.877

1.442020

0.719320 4

1.404020

⫺115.0

115.7

0.727420

1.407820

⫺90.9

118.3

0.975

1.451920

9611mm

73

0.954

1.451020

8911mm

68

Ethyl 3-methylcrotonate, e126 Ethyl methyl ketone, b475 Ethyl 1-methylnipecotate, e216

i aq; sl s alc; s eth

DEAN 37261 (McGHP)

e210a

i aq; s eth

Ethyl 2-methyl-4-oxo-2-cyclohexene-1-carboxylate, c7 Ethyl N-methyl-N-phenylcarbamate, m379 Ethyl 2-methylpipicolinate, e217

RIGHT ROTATED

e209

e211

e212

e213

e216

e217

INTERACTIVE

Ethyl 3-methyl-1piperidine propionate 2-Ethyl-2-methyl-1,3propanediol 5-Ethyl-2-methylpyridine Ethyl methyl sulfide Ethyl (methylthio)acetate N-Ethylmorpholine Ethyl nitrate Ethyl nitrite 4-Ethylnitrobenzene Ethyl 4-nitrobenzoate Ethyl nonanoate Ethyl cis,cis-9,12-octadecadienoic acid Ethyl cis-9-octadecenoate Ethyl octanoate Ethyl oxalyl chloride Ethyl oxamate 2-Ethyl-2-oxazoline Ethyl 2-oxocyclopentanecarboxylate Ethyl 4-oxopentanoate Ethyl 2-oxopropionate 3-Ethylpentane Ethyl pentanoate 2-Ethylphenol 3-Ethylphenol 4-Ethylphenol Ethyl phenylacetate

e219 e220 e221 e222

1.224

e223 e224 e225 e226 e227 e228 e229 e230 e231 e232 e233 e234 e235 e236 e237 e238 e239 e240 e241 e242 e243

Formula weight

Beilstein reference

Density, g/mL

Refractive index

0.945

1.453020

199.30

22, 59

HOCH2C(C2H5)(CH3)CH2OH

118.18

1, 487

C2H5(CH3)C5H3N

121.18

20, 248

0.919

1.497020

CH3CH2SCH3 CH3SCH2CO2C2H5

76.15 134.20

1, 343

0.842 1.043

1.439220 1.458720

115.18 91.13 75.07 151.17 195.17 186.30 308.51

271, 203 1, 329 1, 329 5, 358 9, 390 2, 353 22, 461

0.905 1.10025 4 0.9015 15 1.118 0.866 0.8846

1.421920 1.467520

310.53

2, 467

0.869

1.450020

2, 348 2, 541 2, 544

0.878 1.2223

1.4166 1.416420

(O")(C5H7)CO2C2H5

172.27 136.53 117.10 99.13 156.18

10, 597

0.982 1.054

1.437020 1.448520

CH3C("O)CH2CH2CO2C2H5 CH3C("O)CO2C2H5 (C2H5)3CH CH3(CH2)3CO2C2H5 C2H5C6H4OH C2H5C6H4OH C2H5C6H4OH C6H5CH2CO2C2H5

144.17 116.12 100.20 130.19 122.17 122.17 122.17 164.20

3, 675 3, 616 13, 441 2, 301 5, 470 6, 471 6, 472 9, 434

1.012 1.06016 4 0.698220 4 0.87720 4 1.037 1.001 1.011 1.031

1.422220 1.40816 1.393420 1.373220 1.537220 1.533020 1.5239 1.498020

CH3CH2ONO2 CH3CH2ONO C2H5C6H4NO2 O2NC6H4CO2C2H5 CH3(CH2)7CO2C2H5 H(CH2)5CH"CHCH2CH"CH(CH2)7CO2C2H5 CH3(CH2)7CH"CH(CH2)7CO2C2H5 CH3(CH2)7CO2C2H5 CH3CH2OC("O)C("O)Cl CH3CH2OC("O)C("O)NH2

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

11213mm

99

226

⬎110

178

66

s alc, bz, eth, acid

⫺106

66.7 7225mm

⫺15 59

i aq; misc alc, eth

1.441020 1.384922

⫺63 ⫺94.6

1.544520

⫺32 55–59 ⫺37

139 87.7 17 245–246

27 10 (CC) ⫺35 ⬎110

misc aq, alc, eth 1 aq; misc alc, eth misc alc, eth v s alc, eth

227 1936mm

94 ⬎110

i aq; misc alc, eth misc DMF, oils

⫺32

21615mm

⬎110

i aq; misc alc, eth

⫺43

208 135

75 41

i aq; misc alc, eth d aq, alc; s bz, eth s aq, eth; i bz

128 10211mm

29 77

41–44

114–116 ⫺62

⫺118.6 ⫺91.3 ⫺18 ⫺4 45

205–206 144 93.5 145.5 204 11015mm 218 229

45

78 94 100 77

v s aq; misc alc sl s aq; misc alc, eth i aq; s alc, eth 0.2 aq; misc alc, eth

i aq; misc alc, eth i aq; misc alc, eth

INTERACTIVE

e218

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

e245 e246 e247 e248 e249 e250 e251

Ethyl 3-phenylglycidate 1-Ethylpiperazine Ethyl N-piperazinocarboxylate 1-Ethylpiperidine 2-Ethylpiperidine Ethyl 3-piperidinecarboxylate Ethyl 4-piperidinecarboxylate Ethyl N-piperidinepropionate

192.21

1.518020

960.5mm

⬎110

114.19 158.20

232, 5 232, 9

0.899 1.080

1.469020 1.476520

157 273

43 ⬎110

113.20 113.20 157.21

20, 17 20, 104

0.834 0.858 1.012

1.444020 1.451020 1.460120

131 143 1047mm

18 31 90

s aq

1.010

1.459120

204

80

s aq, alc, bz, eth

0.927

1.454520

217–219

87

157.21 185.27

Ethyl nipecotate, e249 Ethyl oleate, e230 Ethyl oxirane, e3

1.102

20, 62

Ethyl pelargonate, e228 Ethyl pentyl ketone, o37 Ethyl phenyl ether, e36

DEAN 37261 (McGHP)

e244

Ethyl picolinate, e259 Ethylpiperidinol, e186 Ethyl pivalate, e128

1.225 e223

e234

e244

e245

RIGHT

e218

ROTATED

e246

e247

e248

e249

e250

e251

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Ethyl 1-propenyl ether Ethyl propionate Ethyl propyl ether Ethyl propyl sulfide 2-Ethylpyridine 3-Ethylpyridine 4-Ethylpyridine Ethyl 2-pyridinecarboxylate 1-Ethyl-2pyrrolidinone Ethyl salicylate Ethyl sorbate 2-Ethyltoluene 3-Ethyltoluene 4-Ethyltoluene Ethyl 4-toluenesulfonate N-Ethyl-m-toluidine N-Ethyl-o-toluidine 6-Ethyl-o-toluidine 2-(N-Ethyl-mtoluidino)ethanol Ethyl trichloroacetate Ethyltrichlorosilane Ethyltriethoxysilane Ethyltriphenylphosphonium iodide Ethyl undecanoate Ethyl 10-undecenoate Ethylurea N-Ethylurethane

e260

1.226

e261 e262 e262a e262b e262c e263 e264 e265 e266 e267 e268 e269 e270 e271 e272 e273 e274 e275

CH3CH"CHOC2H5 CH3CH2CO2C2H5 CH3CH2OCH2CH2CH3 CH3CH2SCH2CH2CH3 CH3CH2(C5H4N) CH3CH2(C5H4N) CH3CH2(C5H4N)

Formula weight 86.13 102.13 88.15 104.21 107.16 107.16 107.16 151.17

Beilstein reference 1, 435 2, 240 1, 354 13, 1432 20, 241 20, 242 20, 243 22, 35

113.16

Density, g/mL

Refractive index

0.778 0.891720 0.739 0.8270 0.937 0.954 0.942 1.1194

1.398020 1.383920 1.369520 1.446220 1.496420 1.501520 1.500920 1.508820

0.992

1.465220

C6H4(OH)CO2C2H5 CH3CH"CHCH"CHCO2C2H5 CH3C6H4C2H5 CH3C6H4C2H5 CH3C6H4C2H5 CH3C6H4SO2OC2H5

166.18 140.18 120.19 120.19 120.19 200.26

10, 73 2, 484 51, 192 5, 398 5, 397 11, 99

1.131 0.956 0.865 0.865 0.861 1.16645 4

1.521920 1.494220 1.504020 1.496020 1.495020 1.511020

CH3C6H4NHC2H5 CH3C6H4NHC2H5 C2H5C6H3(CH3)NH2 CH3C6H4N(C2H5)CH2CH2OH

135.21 135.21 135.21 179.26

12, 857

0.957 0.938 0.968 1.019

1.545120 1.547020 1.552520 1.554020

Cl3CCO2C2H5 C2H5SiCl3 C2H5Si(OC2H5)3 C2H5P(C6H5)3I

191.44 163.51 192.33 418.26

2, 209 4, 630 44, 4223 16, 760

1.38320 4 1.238 0.895

1.444720 1.425220 1.392020

CH3(CH2)10CO2C2H5 H2C"CH(CH2)8CO2C2H5 CH3CH2NHC("O)NH2 CH3CH2NHCO2C2H5

214.35 212.34 88.11 117.15

2, 358 2, 459 4, 115 4, 114

0.859 0.879 1.21318 0.98120 4

Melting point,⬚C

⫺73.9 ⫺79 ⫺117.0

2

2–3 ⫺81 ⫺95 ⫺62 33

⫺33

⫺106

Boiling point,⬚C

Flash point,⬚C ⫺18 12 32

Solubility in 100 parts solvent

67–76 99 62–63 118.5 149 162–165 168 240–241

29 48 47 107

9720mm

76

232–234 195.5 165 161 162 17315mm

107 69 39 38 36 157

221 218 231 1151mm

89 88 89 ⬎110

168 99 158–166

65 13 38

i aq; s alc, eth

1054mm 258–259

⬎110 ⬎110

i aq; s org solvents

8520mm

75

1.7 aq; misc alc, eth sl s aq; misc alc, eth s alc sl s aq; s alc, eth v s alc, eth; sl s aq sl s aq; s alc, eth misc aq, alc, eth

misc alc, eth; sl s aq

i aq; s alc, eth

169–171 1.428020 1.439020 93–96 1.421120

v s aq; 80 alc; i eth 63 aq

INTERACTIVE

e252 e253 e254 e255 e256 e257 e258 e259

Formula

ROTATED

Name

LEFT

No.

1.227

e279

Ethyl vinyl ether N-Ethyl-2,3-xylidine 1-Ethynyl-1cyclohexanol Eugenol

f1 f2 f3 f4 f5 f6 f7 f8 f9 f10 f11 f12 f13

Fluoranthene Fluorene Fluorenone Fluorescein Fluoroacetic acid 4-Fluoroacetophenone 2-Fluoroaniline 4-Fluoroaniline 2-Fluorobenzaldehyde 4-Fluorobenzaldehyde Fluorobenzene 2-Fluorobenzoic acid 4-Fluorobenzoic acid

CH3CH2OCH"CH2 (CH3)2C6H3NHC2H5 HOC6H10C#CH

72.11 149.24 124.18

4-(H2C"CHCH2)C6H32-(OCH3)OH

FCH2CO2H FC6H4COCH3 FC6H4NH2 FC6H4NH2 FC6H4CHO FC6H4CHO C6H5F FC6H5CO2H FC6H5CO2H

1, 433 12, 1101 62, 100

0.758920 0.917 0.967

164.20

6, 961

1.066

202.26 166.22 180.21 332.31 78.04 138.14 111.12 111.12 124.11 124.11 96.11 140.11 140.11

5, 685 5, 625 7, 465 19, 222 2, 193

1.25204 1.20304 1.130099 4

121, 296 12, 597 71, 132 71, 132 5, 198 9, 333 9, 333

1.138 1.151 1.1725 1.178 1.157 1.024020 4 1.46025 4 1.47925 4

Ethyl toluates, e204, e205, e206 Ethyl p-tolyl ether, m373 Ethyl trimethylacetate, e128 Ethyl vanillin, e46 Ethyne, a41 Ethynylbenzene, p84

1-Ethyl-1-propanol, p41 Ethyl propenoate, e60 1-Ethylpropylamine, a247a Ethyl pyruvate, e237 2-(Ethylthio)ethanol, e180 Ethyl thioglycolate, e196

31–33

35 228 180

⬍ ⫺45 71 62

1.5410

⫺12/⫺10

254

⬎110

1.636999

108 115 82–85 320 33

384 295 342

1.376720 1.546820

20

1.511020 1.542020 1.539520 1.522020 1.520020 1.465720

⫺116

⫺29 ⫺2 ⫺44.5 ⫺10 ⫺42.2 123–125 184–187

165 196 183 187 9146mm 181 84.7

0.9 aq; s alc, eth 2.4 aq; misc alc, bz, acet, ketones, PE

sl s alc; s bz, eth v s HOAc; s bz, eth s alc, bz; v s eth s hot alc, hot HOAc sl s aq, alc 71 60 73 55 56 ⫺15

DEAN 37261 (McGHP)

e276 e277 e278

sl s aq; s alc, eth

0.15 aq; misc alc sl s aq; s alc, eth 0.1 aq; s alc, eth

Eugenol, m108 Eugenol methyl ether, a84 Fenchone, t376 Fenchyl alcohol, t375 N-9H-(2-Fluorenyl)acetamide, a13

RIGHT ROTATED

e259

e260

f1

f2

f3

f4

INTERACTIVE

No. f14 f15 f16 f17 f18 f19 f20 f21

1.228

f22 f23 f24

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

FC6H5COCl

158.56

91, 136

1.328

1.536520

4

9215mm

82

FC6H5COCl

158.56

91, 137

1.342

1.529620

9

8220mm

82

FC6H5CH2Cl

144.58

1.207

1.513020

8226mm

60

CH3CH2F CH3F FC6H4OCH3

48.06 34.04 126.13

1, 82 1, 59

FC6H4OCH3

126.13

61, 98

76.11

14, 286

FC6H3(NO2)NH2 FC6H4NO2

156.12 141.10

12, 729 5, 241

CH3C6H3(NO2)F

155.13

FC6H4OH F(C5H4N) FC6H4CH3 FC6H4CH3 FC6H4CH3 FCCl3

112.10 97.09 110.13 110.13 110.13 137.37

H2C"O HC("O)NH2 HC("NH)NH2 · HO2CCH3 H2NC("NH)S(O)OH C6H5NHCHO HCO2H HO2CC6H4HCO

(CH3)3CF

⫺143.2 ⫺141.8

1.195 g/L 1.104

1.488020

1.114

1.487720

⫺37.7 ⫺78.4 158743mm

43

⫺45

157

43

⫺77

12

⫺12

Solubility in 100 parts solvent

198 mL aq; v s alc, eth 166 mL aq; v s alc, eth

s eth

1.330020 4

1.531220

96–98 21

205

91 83

1.262

1.524020

28–30

241

⬎110

6, 183 201, 80 5, 290 5, 290 5, 290 1, 64

46–48 1.128 1.001417 0.997420 0.997520 1.494

1.468020 1.471617 1.469120 1.469820 1.382120

185 126 115 115 117 24

68 28 12 9 17 none

30.03 45.04 104.11 108.12

1, 558 2, 26

0.815⫺420 1.133420 4

0.8153⫺20 1.447520

⫺92 2.6 158 dec 126 dec

⫺19.5 220

56 154

122 aq; s alc, eth misc aq, alc, acet

121.14 46.03 150.13

12, 230 2, 8 10, 666

1.144 1.22020 4 1.404

1.370420

47 8.3 96–98

271 100.8

⬎110 68

2.5 aq misc aq, alc, eth s aq; v s alc, eth

31, 36

⫺62 ⫺87 ⫺56 ⫺110

i aq; s alc, eth

v s alc, eth s alc, eth s alc, eth

INTERACTIVE

f35 f36 f37

Formula weight

ROTATED

f31 f32 f33 f34

2-Fluorobenzoyl chloride 4-Fluorobenzoyl chloride 4-Fluorobenzyl chloride Fluoroethane Fluoromethane 3-Fluoro-1-methoxybenzene 4-Fluoro-1-methoxybenzene 2-Fluoro-2-methylpropane 4-Fluoro-3-nitroaniline 1-Fluoro-4-nitrobenzene 4-Fluoro-3-nitrotoluene 4-Fluorophenol 2-Fluoropyridine 2-Fluorotoluene 3-Fluorotoluene 4-Fluorotoluene Fluorotrichloromethane Formaldehyde Formamide Formamidine acetate Formamidinesulfinic acid Formanilide Formic acid 2-Formylbenzoic acid

Formula

LEFT

f25 f26 f27 f28 f29 f30

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Formylhydrazine 4-Formylmorpholine N-Formylpiperidine D-(⫺)-Fructose Fumaric acid Fumaroyl dichloride 2-Furaldehyde Furan 2-Furanacrylic acid

f47 f48

2,5-Furandimethanol 2-Furanmethanethiol

HC("O)NHNH2

HO2CCH"CHCO2H ClC("O)CH"CHC("O)Cl

60.06 115.13 113.16 180.16 116.07 152.96 96.09 68.07 138.12

2, 93 273, 274 20, 45 31, 321 2, 737 2, 743 172, 305 17, 27 18, 300

128.13 114.17

171, 90 172, 116

54–56 1.484820 1.478020

1.145 1.019 1.63520 4 1.40820 1.159820 4 0.951420

1.498820 1.526220 1.421420

1.132

1.530420

287

⬎110 ⬎110 91

73 60 ⫺35

74–76

1.229

Formylphenols, h94, h95, h96 Formylpyridines, p261, p262, p263 Freon-11, t237 Freon-12, d218 Freon-12B2, d93 Freon-21, d233

Fluorothane, b308 Fluorotrichloromethane, t237 2-Fluoro-5-(trifluoromethyl)aniline, a179 Formal, d507 Formaldehyde diethyl acetal, d307 Formic acid hydrazide, f38 Formylamide, f33

⫺36.5 ⫺85.6 142–144

236–237 222 122 dec subl 300 161–164 161.8 31.4 286

155

45

v s alc, chl, eth; s bz

v s aq; 6.7 alc; s pyr 0.6 aq; 9 alc; 0.7 eth dec aq, alc 8 aq; misc alc, eth 1 aq; misc alc, eth 0.2 aq; 1.1 bz; s alc, eth, HOAc

DEAN 37261 (McGHP)

f38 f39 f40 f41 f42 f43 f44 f45 f46

Freon-22, c101 Freon-114, d271 2,5-Furandione, m2 2-Furanmethanol, f50 Furfural, f44 2-Furfuraldehyde, f44

RIGHT

f45

f40

f41

f46

f44

f47

ROTATED

f39

f48

INTERACTIVE

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

1.230

f49 f50

Furfuryl acetate Furfuryl alcohol

140.14 98.10

172, 115 17, 112

1.117520 4 1.129520 4

1.461820 1.486820

f51 f52 f53 f54 f55 g1 g2

Furfurylamine Furfuryl methacrylate ␣-Furildioxime 2-Furoic acid 2-Furoyl chloride D-(⫹)-Galactose Geraniol

18, 584 173, 1248 19, 166 18, 272 18, 276 31, 295 1, 457

1.099520 4 1.078

1.490020 1.482020

g3

Geranyl acetate

196.29

2, 140

g4

Gerard reagent P

(CH3)2C"CHCH2CH2C(CH3)"CHCH2OH (CH3)2C"CHCH2CH2C(CH3)"CHCH2O2CCH3 [(C5H5N)CH2C("O)NHNH2]⫹ Cl⫺

97.12 166.18 220.18 112.08 130.53 180.16 154.25

187.63

g5

Gerard reagent T

[(CH3)3NCH2C("O)NHNH2]⫹ Cl⫺

g6 g7 g8

D-Gluconic

acid ␦-Gluconolactone ␣-D-(⫹)-Glucose

196.16 178.14 180.16

Merck: 12, 4436 Merck: 12, 4436 3, 542 181, 405 31, 83

g9

390.34

31, 119

109–111

176.12

176–178

27 aq; 2.8 MeOH

g12 g13

␣-D-Glucose pentaacetate D-Glucurono-3,6lactone (S)-(⫹)-Glutamic acid (S)-(⫹)-Glutamine

less soluble in polar solvents than T v s aq, HOAc, glyc, ethylene glycol v s aq; sl s alc; i eth 50 aq; 1 alc; i eth 91 aq; 0.83 MeOH; s pyr 0.15 aq; 1.3 alc; 3 eth

g14 g15 g16 g17

2, 631

Glutaric anhydride Glutaric dialdehyde Glutaronitrile

OCHCH2CH2CH2CHO NCCH2CH2CH2CN

114.10 100.12 94.12

17, 411 1, 776 2, 635

145–146 825mm

46 90

i aq; s alc, eth misc aq(dec); v s alc, eth misc aq; s alc, eth

1.324

1.531020

0.889420 4

1.476620

230

76

v s alc, eth; sl s bz 4 aq; s alc; v s eth dec aq, alc; s eth 200 aq; s pyr; sl s alc i aq; misc alc, eth

0.917415 15

1.462815

13825mm

104

v s alc; misc eth

230–232 170

85

dec 200 192 131 153 153–156

1.562018 4

1.53820 4

1.42920 4

1.4188106

0.988823

1.433825 1.434520

d 247 185 dec

subl 200

98

303

55–57

15010mm 187–189 286

⫺29

0.8 aq; i alc, eth 5 aq; 0.0035 MeOH; i bz, chl, eth, acet 43 aq20; v s alc, eth; s bz, chl; sl s PE ⬎110 none ⬎110

s aq, alc s aq, alc, chl; i eth

INTERACTIVE

132.12

166–168 133–134 ⫺2 167

65 75

ROTATED

147.13 146.15

Glutaric acid

HO2CCH2CH2CH(NH2)CO2H H2NC("O)CH2CH2CH(NH2)CO2H HO2CCH2CH2CH2CO2H

Merck: 11, 4362 4, 488 4, 491

⫺70

175–177 171

LEFT

g11

167.64

⫺31

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Glutaryl dichloride Glycerol Glyceryl tris(butyrate)

ClC("O)(CH2)3C("O)Cl HOCH2CH(OH)CH2OH (CH3CH2CH2CO2CH2)2CHO2CCH2CH2CH3

Furfuryl mercaptan, f48 Furylacrylic acid, d46 2-Furyl methyl ketone, a44 Galactitol, d824

169.01 92.09 302.37

2, 634 1, 502 2, 273

1.324 1.261320 1.03220 4

1.472020 1.474620 1.435920

18 ⫺75

Gallic acid, t319 Gentisic acid, d432 Geranial, d665 D-Glucitol, s5

1.231

f49

f50

dec aq, alc; s eth misc aq, alc; 0.2 eth i aq; v s alc, eth

Glutaraldehyde, g16 Glycerol dichlorohydrin, d264 Glycerol ␣-monochlorohydrin, c227 Glyceryl triacetate, p200

f51

f55

106 199 173

f52

g1

f53

g6

RIGHT

f54

216–218 290 287–288

DEAN 37261 (McGHP)

g18 g19 g20

g7

ROTATED

g8

g9

g11

g12

g13

g15

INTERACTIVE

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

[CH3(CH2)10CO2CH2]2CHO2C(CH2)10CH3 O2NOCH2CH(ONO2)CH2ONO2

639.02

2, 362

0.89460 4

1.440460

46

g22

Glyceryl tris(dodecanoate) Glyceryl tris(nitrate)

227.09

1, 516

1.59420 4

1.478612

13.3

1605mm

g23

Glyceryl tris(oleate)

885.46

4, 468

0.91515 4

1.462140

⫺4/⫺5

23515mm

g24

Glyceryl tris(palmitate)

807.35

2, 373

0.866380 4

1.438180

65–66

310–320

v s bz, chl, eth

g25

723.18

2, 367

0.88560 4

1.442860

57

v s alc, bz, chl

g26 g27 g28

Glyceryl tris(tridecanoate) Glycine N-Glycylglycine Glyoxal

[CH3(CH2)7CH"CH(CH2)7CO2CH2]2CHO2C(CH2)7CH"CH(CH2)7CH3 [CH3(CH2)14CO2CH2]2CHO2C(CH2)14CH3 [CH3(CH2)11CO2CH2]2CHO2C(CH2)11CH3 H2NCH2CO2H H2NCH2C("O)NHCH2CO2H HC("O)CHO

0.18 aq; 54 alc; misc eth s chl, eth, CCl4

75.07 132.12 58.04

4, 333 4, 371 1, 759

1.1607 1.382620

dec 240 260 dec 15

g29 g30 g31

Glyoxylic acid Guanidine Guanine

HC("O)CO2H H2NC("NH)NH2

74.04 59.07 151.13

3, 594 3, 82 26, 449

h1 h1a h2

Heptadecane 1-Heptadecanol Heptafluorobutyric acid Heptaldehyde 2,2,4,4,6,8,8-Heptamethylnonane 1,1,1,3,5,5,5-Heptamethyltrisiloxane Heptane Heptanedioic acid 1-Heptanethiol

CH3(CH2)15CH3 CH3(CH2)16OH CF3CF2CF2CO2H

140.41 256.48 214.04

1, 173 11, 220

25 aq; 0.6 pyr; i eth s hot aq; sl s alc viol rxn aq; s anhyd solvents; mixtures with air may explode v s aq; sl s alc, eth v s aq, alc s alk soln, dil acids; sl s alc, eth s eth; sl s alc

CH3(CH2)5CHO (CH3)3CCH2C(CH3)2CH2CH(CH3)CH2C(CH3)3 [(CH3)3SiO]2SiHCH3

114.19 226.45

CH3(CH2)5CH3 HO2C(CH2)5CO2H CH3(CH2)6SH

g21

1.232

1.436025

1.625

⬍1.30020

12, 750

0.821615 4 0.793

1.428520 1.439120

222.51

43, 1874

0.819

1.382020

100.21 160.17 132.27

1, 154 2, 670 1, 415

0.683820 4 1.32915

1.387720

50.4

dec 160

22.0 53.8

302.2 333 120

148 ⬎110 none

⫺43

153 240

35 95

142

27

98.4 21210mm 176.9

⫺4 (CC)

⫺90.6 105.8 ⫺43.2

46

misc alc, eth; sl s aq

s alc, chl, eth 5 aq; v s alc, eth i aq

INTERACTIVE

h6 h7 h8

0.776722

explodes 270

ROTATED

h5

98 ca. 50 ⬎300

v s bz, eth; sl s alc

LEFT

h3 h4

1.14

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

1.233

h24

Heptanoic acid Heptanoic anhydride 1-Heptanol 2-Heptanol 3-Heptanol 2-Heptanone 3-Heptanone 4-Heptanone Heptanoyl chloride 1-Heptene cis-2-Heptene trans-2-Heptene 1-Heptylamine 1-Heptyne Hexachloroacetone Hexachlorobenzene Hexachloro-1,3butadiene 1,2,3,4,5,6-Hexachlorocyclohexane, ␥isomer

130.19 242.36 116.20 116.20 116.20 114.19 114.19 114.19 148.63 98.90 98.19 98.19 115.22 96.17 264.75 284.78 260.76

2, 338 2, 340 1, 414 1, 415 11, 205 1, 699 1, 699 1, 699 2, 340 1, 219 13, 825 1, 219 4, 193 1, 256 1, 657 5, 205 1, 250

0.918120 4 0.923 0.821920 4 0.816720 0.822720 0.819715 4 0.819720 20 0.817 0.960 0.697020 0.70820 0.701220 0.777 0.733 1.743 2.04424 1.655

C6H6Cl6

290.83

51, 8

1.8720

Glycolaldehyde, h87 Glycolaldehyde diethyl acetal, d305 Glycolic acid, h88 Glycol methacrylate, h126 Glyoxaline, i3 Guaiacol, m97 Heliotropin, m250 Hemimellitene, t357

1.422120 1.433220 1.424220 1.421010 1.421420 1.411615 1.405520 1.406820 1.430020 1.399920 1.40620 1.404520 1.424320 1.407520 1.511220 1.555020

⫺8 ⫺12.4 ⫺34 ⫺70 ⫺35 ⫺39 ⫺32.1 ⫺120 ⫺109.5 ⫺23 ⫺81 ⫺30 232 ⫺21

222 268 176.4 159 157 151 147 143.7 173 93.6 98.4 98 154–56 99–100 666mm 325 215

113–115

Hemimellitic acid, b29 Heptaldehyde, h3 sec-Heptyl alcohol, h12 Heptyl bromide, b343 Heptyl chloride c147 Heptyl iodide, i34 Heptyl mercaptan, h8 Heptyl methyl ketone, n99

⬎110 ⬎110 73 71 60 39 46 48 (CC) 58 ⫺8 ⫺6 ⫺1 35 ⫺2 none 242 none

0.25 aq; s alc, eth i aq; s alc, eth misc alc, eth 0.35 aq; s alc, bz, eth sl s aq s alc, eth 0.43 aq; s alc, eth 0.53 aq; misc alc, eth dec aq, alc; s eth 0.1 aq; s alc, eth

s alc, acet, eth, PE sl s aq; s acet s bz, chl, eth s alc, eth s bz, chl

RIGHT

Glyceryl tris(laurate), g21 Glyceryl tris(myristate), g25 Glycidic acid, h88 Glycidol, e16 Glycidyl methacrylate, e17 Glycidyl phenyl ether, e14 Glycinol, e29 Glycinonitrile, a103

CH3(CH2)5CO2H [CH3(CH2)5CO]2O CH3(CH2)6OH CH3(CH2)5CH(OH)CH3 CH3(CH2)3CH(OH)CH2CH3 HC3(CH2)4C("O)CH3 CH3(CH2)3C("O)CH2CH3 CH3(CH2)2C("O)(CH2)2CH3 CH3(CH2)5C("O)Cl CH3(CH2)4CH"CH2 CH3(CH2)3CH"CHCH3 CH3(CH2)3CH"CHCH3 CH3(CH2)6NH2 CH3(CH2)4C#CH Cl3CC("O)CCl3 CCl6 CL2C"CClCCl"CCl2

DEAN 37261 (McGHP)

h9 h10 h11 h12 h13 h14 h15 h16 h17 h18 h18a h18b h19 h20 h21 h22 h23

ROTATED

g31

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No. h25 h27 h28

1.234

h44 h45 h46

Beilstein reference

272.77

Density, g/mL

Refractive index

1.70125 4

1.564420

Cl3CCCl3

236.74 370.83

1, 87 93, 4049

2.091

CH3[C6H(Cl)3OH]2 Cl3CC(Cl)"CCl2 CH3(CH2)14CH3 CH3(CH2)13CH(OH)CH2OH CH3(CH2)15SH CH3(CH2)14CO2H CH3(CH2)15OH CH3(CH2)14CH"CH2 CH3(CH2)15NH2 CH3CH"CHCH"CHCHO H2C"CHCH2CH2CH"CH2 CH3CH"CHCH"CO2H

406.91 248.75 226.45 258.45 258.51 256.43 242.45 224.43 241.46 96.13 82.15 112.13

63, 5407 1, 200 1, 172 13, 2244 1, 430 2, 370 1, 429 1, 226 4, 202 12, 809 1, 253 2, 483

C6F6 F3CCF3 (CF3)2CHOH

186.05 138.01 168.04

53, 523 13, 132

CF3CF"CF2 [-Si(CH3)2O-]3

150.02 222.48

13, 697 43, 1884

(CH3)3SiNHSi(CH3)3

161.40

4,3, 1861

0.77420 4

1.407120

(CH3)3SiOSi(CH3)3

162.38 99.18

43, 1859 20, 94

0.76420 4 0.880

1.377520 1.463120

Melting point,⬚C

Boiling point,⬚C

1.548020 1.434520

0.840 0.85262 4 0.811660 0.78320 4

1.472020 1.427380 1.435560 1.4401

0.871 0.692320 4

1.538620 1.404220

1.618220 1.590⫺78 1.59625

1.378120 1.275020

Solubility in 100 parts solvent

⫺10

239

none

187 239–242

sublimes

none

s alc, bz, chl, eth

210 286.8

none none 135

misc eth

163–165 1.765 0.773320 4

Flash point,⬚C

18.2 72–74 18–20 62 49.3 4.1 45–48

101

⫺140.7 134.5

1847mm 351 334 284 330 7630mm 59.5 11910mm

5.1 ⫺100.7 ⫺3

80.3 ⫺78.3 58.2

10 none

⫺153 64–66

⫺28 133–135

35

126

8

101 138749mm

⫺2 18

⫺67

135 132 140 67 ⫺27 127

sl s alc, s eth s hot: chl, eth s alc, chl, eth s alc, eth, PE v s alc, eth; s bz, chl s alc, eth 0.2 aq; 13 alc; 9 acet; 2.3 bz; 11 diox; 1 CCl4 sl s alc, eth s aq, bz, CCl4

INTERACTIVE

h47 h48

Hexafluorobenzene Hexafluoroethane 1,1,1,3,3,3-Hexafluoro2-propanol Hexafluoropropene Hexamethylcyclotrisiloxane 1,1,1,3,3,3-Hexamethyldisilazane Hexamethyldisiloxane Hexamethyleneimine

Formula weight

ROTATED

h41 h42 h43

Hexachlorocyclo-1,3pentadiene Hexachloroethane 1,4,5,6,7,7-Hexachloro5-norbornene-2,3-dicarboxylic anhydride Hexachlorophene Hexachloropropene Hexadecane 1,2-Hexadecanediol 1-Hexadecanethiol Hexadecanoic acid 1-Hexadecanol 1-Hexadecene 1-Hexadecylamine 2,4-Hexadienal 1,5-Hexadiene 2,4-Hexadienoic acid

Formula

LEFT

h29 h30 h31 h32 h33 h34 h35 h36 h37 h38 h39 h40

Name

h50 h51 h52 h53 h54 h55 h56 h57 h58 h59

1.235

h60 h61 h62 h63

Hexamethylenetetramine Hexamethylphosphoramide Hexanaldehyde Hexane 1,6-Hexanediamine 1,6-Hexanedioic acid DL-1,2-Hexanediol 1,6-Hexanediol 2,5-Hexanediol 1,6-Hexanediol diacrylate 1,6-Hexanediol dimethacrylate 2,5-Hexanedione Hexanenitrile 1-Hexanethiol 1,2,6-Hexanetriol

140.19 [(CH3)2N]3P("O)

1, 583

1.02720

179.20

CH3(CH2)4CHO CH3(CH2)4CH3 H2N(CH2)6NH2 HO2C(CH2)4CO2H CH3(CH2)3CH(OH)CH2OH HO(CH2)6OH CH3CH(OH)CH2CH2CH(OH)CH3 [H2C"CHCO2(CH2)3⫺]2

100.16 86.18 116.21 146.14 118.18 118.18 118.18 226.28

[H2C"C(CH3)CO2(CH2)3⫺]2

254.33

CH3C("O)CH2CH2C("O)CH3 CH3(CH2)4CN CH3(CH2)5SH HOCH2CH(OH)(CH2)3CH2OH

114.14 97.16 118.24 134.17

1.331⫺5

2

1 , 745 1, 142 4, 269 2, 649 11, 251 1, 484 1, 485

1, 788 2, 324 13, 1659 14, 2784

280 subl 1.458820

20 4 20 4

20

0.8335 0.6594

1.4035 1.374920

1.36025 4 0.951 0.958 0.961745 16 1.010

1.442520 1.457925 1.446520 1.456220

0.995

1.458020

0.97320 4 0.805220 0.842420 4 1.106320 20

1.426020 1.406920 1.449620 1.5820

Hexahydrobenzene, c347 Hexahydrobenzoic acid, c353 Hexahydrobenzylamine, c362 Hexahydrophthalic acid, c356 Hexahydropyridine, p180 Hexamethylenediamine, h53 Hexamethylene diisocyanate, d461

67 aq; 8 alc; 10 chl

7

232740mm

105

misc aq

⫺56 ⫺95.4 42 152–154

131 68.7 205 337.5 223–224 208 220.8

32 ⫺22 81 196 ⬎110 101 101 ⬎110

v s alc, eth; sl s aq misc alc, chl, eth v s aq; sl s alc, bz 1.4 aq; v s alc; s acet

⬎ 350

⬎110

188 163.6 152.7 1785mm

78 43 20 191

42.8 ⫺50

⫺9 ⫺80.3 ⫺80.5 ⫺32.8

v s aq, alc s aq, alc, eth

misc aq, alc, eth i aq; s alc, eth i aq; v s alc, eth misc alc, acet; i bz

Hexamethylene glycol, h56 Hexamethylethane, t100 2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosene, s8 1,6,10,15,19,23-Hexamethyltetracosane, s7 1,6-Hexanedinitrile, d284 6-Hexanelactam, o61

RIGHT

Hexachloro-2-propanone, h21 ␣,␣,␣,␣⬘,␣⬘,␣⬘-Hexachloro-p-xylene, b225 Hexadecyl mercaptan, h33 ␣,␣,␣,␣⬘,␣⬘,␣⬘-Hexafluoro-3,5-xylidine, h229 Hexahydroaniline, c375 Hexahydro-2H-azepin-2-one, o61 Hexahydrobenzaldehyde, c352

250

DEAN 37261 (McGHP)

h49

ROTATED

h25

h28

h48

h49

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

1.236

116.16 214.31 102.18

2, 321 2, 324 1, 407

0.926520 4 0.926 0.813620

1.416820 1.428020 1.418220

⫺3 ⫺41 ⫺44.6

205 246–248 157.5

102 ⬎110 63

h67 h68 h69 h70 h71 h72 h73 h74 h75 h76 h77 h78

2-Hexanol 3-Hexanol 6-Hexanolactone 2-Hexanone 3-Hexanone Hexanoyl chloride 1-Hexene trans-2-Hexenoic acid trans-3-Hexenoic acid trans-2-Hexen-1-ol 5-Hexen-2-one trans-2-Hexenyl acetate Hexyl acetate Hexyl acrylate Hexylamine 1-Hexyne L-Histidine Hydantoin Hydrazine

CH3(CH2)3CH(OH)CH3 CH3CH2CH2CH(OH)CH2CH3

102.18 102.18 114.14 100.16 100.16 134.61 84.16 114.14 114.14 100.16 98.15 142.20

1, 408 1, 408 172, 290 1, 689 1, 690 2, 324 1, 215 24, 1563 2, 435 12, 486 1, 734 22, 151

0.810825 4 0.819320 4 1.030 0.811320 0.815 0.975420 4 0.673220 0.965 0.963 0.849 0.847 0.898

1.412825 1.416020 1.463020 1.400720 1.400220 1.426320 1.387920 1.488520 1.439820 1.434320 1.419720 1.427520

⫺47

139.9 135 215 127.6 123 153 63.5 217 11922mm 158–160 128–129 166

41 41 109 25 35 50 ⫺9 ⬎110 ⬎110 54 23 58

144.21 156.23 101.19 82.14 155.16 100.08 32.05

0.86020 20 0.888 0.76325 4 0.715220 4

1.409020 1.428020 1.418020 1.398920

⫺81

45 68 8 ⫺21

1.003625 4

1.470020

⫺23 ⫺131.9 282 dec 221–223 1.4

171 9024mm 133 71.3

113.5

52

1.332

172

286

93–94 80 98–100

11012mm 100 325 sl d

⫺17

146

h79 h80 h81 h82 h83 h84 h85

CH3(CH2)3C("O)CH3 CH3CH2CH2C("O)CH2CH3 CH3(CH2)4C("O)Cl CH3(CH2)3CH"CH2 CH3(CH2)2CH"CHCO2H CH3CH2CH"CHCH2CO2H CH3CH2CH2CH"CHCH2OH H2C"CHCH2CH2C("O)CH3 CH3C("O)CH2CH"CHCH2CH2CH3 CH3(CH2)5O2CCH3 H2C"CHCO2(CH2)5CH3 CH3(CH2)5NH2 CH3(CH2)3C#CH

h86

1,4-Hydroquinone

C6H4-1,4-(OH)2

110.11

2, 132 23, 1228 4, 188 1, 253 25, 513 24, 242 Merck: 12, 4809 6, 836

h87 h88 h89

Hydroxyacetaldehyde Hydroxyacetic acid 1⬘-Hydroxy-2⬘-acetonaphthone Hydroxyacetone

HOCH2CHO HOCH2CO2H C10H6(OH)C("O)CH3

60.05 76.05 186.21

1, 817 3, 228 8, 149

1.366100

74.08

11, 84

1.082

h90

H2NNH2

HOCH2C("O)CH3

15

1.431520

⫺18 ⫺55.5 ⫺87 ⫺139.8 33–35 11–12

1.1 aq; v s alc, eth s alc 8 aq; misc bz, eth; s alc sl s aq; s alc, eth

v s alc, eth dec aq, alc; s eth 0.005 aq

0.13 aq; v s alc, eth sl s aq; misc alc, eth i aq; s alc, eth 41 aq; v sl s alc s alc, alk; sl s eth misc aq, alc 7 aq; v s alc, eth; sl s bz v s aq, alc; sl s eth s aq, alc, acet, eth i aq; v s bz; s HOAc

56

misc aq, alc, eth

INTERACTIVE

CH3(CH2)4CO2H [CH3(CH2)4C("O)]2O CH3(CH2)5OH

ROTATED

Hexanoic acid Hexanoic anhydride 1-Hexanol

LEFT

h64 h65 h66

Solubility in 100 parts solvent

h92 h93 h94 h95 h96 h97 h98 h99

2⬘-Hydroxyacetophenone 3⬘-Hydroxyacetophenone 4⬘-Hydroxyacetophenone 2-Hydroxybenzaldehyde 3-Hydroxybenzaldehyde 4-Hydroxybenzaldehyde 2-Hydroxybenzaldehyde oxime 2-Hydroxybenzamide 2-Hydroxybenzoic acid

HOC6H4C("O)CH3

136.15

8, 85

1.13121 4

1.558420

4–6

213717mm

HOC6H4C("O)CH3

136.15

8, 86

1.100100

1.535100

87–89

296

100

HOC6H4C("O)CH3

136.15

8, 87

1.109

C6H4(OH)CHO

122.12

8, 31

1.167420

C6H4(OH)CHO

122.12

8, 58

C6H4(OH)CHO

122.12

8, 64

C6H4(OH)CH"NOH

137.14

8, 49

C6H4(OH)C("O)NH2 C6H4(OH)CO2H

137.14 138.12

10, 87 10, 43

1.237

1.129130 4

s aq; v s alc, bz, eth

3mm

109–111

148

v s alc, eth; sl s aq

⫺7

196.7

103–105

19150mm

s alc, bz, eth; sl s aq

57

dec

1 aq; 70 acet; 4 bz65; v s alc, eth v s alc, bz, eth, acids

140 157–159

dec 270 21120mm

78

117–119

1.44320 4

Hexyl methyl ketone, o36 Hexyl propyl ketone, d20 Hippuric acid, b70 Homocysteine, a200 Homopiperidine, h48 Homoveratric acid, d513 Homoveratrylamine, d517 Hydroacrylonitrile, h173 2-Hydrazinoethanol, h125

misc alc, eth; sl s aq

Hydrazobenzene, d757 Hydrindene, i10 Hydrocinnamic acid, p150 Hydroquinone, d430 Hydroquinone dimethyl ether, d495 Hydroxyacetanilides, a15 thru a17 Hydroxybenzene, p65 2-Hydroxybenzenemethanol, h107

1.7 aq86; s alc, eth

0.2 aq; s alc, chl, eth 0.2 aq; 37 alc; 33 eth; 33 acet; 2 chl; 0.7 bz

RIGHT

D-erythro-Hex-2-enonic acid ␥-lactone, i69 Hexyl alcohol, h66 sec-Hexyl alcohol, e95 sec-Hexylamine, m371 Hexylbenzene, p116 Hexyl bromide, b346 Hexyl chloride, c149 Hexylene glycol, m360 Hexyl iodide, i36

1.574020

⬎110

DEAN 37261 (McGHP)

h91

ROTATED

h69

h83

h84

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

3-Hydroxybenzoic acid 4-Hydroxybenzoic acid 4-Hydroxybenzoic hydrazide 4-Hydroxybenzophenone 1-Hydroxybenzotriazole 6-Hydroxy-1,3-benzoxathiol-2-one 2-Hydroxybenzyl alcohol 1-Hydroxy-2-butanone 3-Hydroxy-2-butanone 4-Hydroxycinnamic acid 7-Hydroxycoumarin 1-Hydroxy-1-cyclohexanecarbonitrile 2-Hydroxy-3,5-diiodobenzoic acid 4-Hydroxy-3,5-dinitrobenzoic acid 3-Hydroxydiphenylamine (2-Hydroxydiphenyl)methane (4-Hydroxydiphenyl)methane

h101 h102 h103 h104

1.238

h105 h106 h107 h108 h109 h111 h112 h113 h114 h115 h116 h117

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

C6H4(OH)CO2H

138.12

10, 134

1.473

201–203

0.8 aq; 10 eth

C6H4(OH)CO2H

138.12

10, 149

1.4684

215–217

0.2 aq; v s alc; 23 eth

HOC6H4C("O)NHNH2

152.15

10, 174

266 dec

HOC6H4C("O)C6H5

198.22

82, 184

132–135

135.13

26, 41

155–158

168.17

194, 2508

158–160

HOC6H4CH2OH

124.13

6, 891

1.16125

CH3CH2C("O)CH2OH CH3C("O)CH(OH)CH3 HOC6H4CH"CHCO2H

88.11 88.11 164.16

1, 826 1, 827 10, 297

1.026 0.997217 4

1.428220 1.417120

C6H10(OH)CN

162.14 125.17

18, 27 10, 5

1.031

1.457620

I2C6H2(OH)CO2H

389.91

10, 113

232–235

HOC6H2(NO2)CO2H

228.12

1, 183

245 dec

HOC6H4NHC6H5

185.23

13, 410

80–82

340

HOC6H4CH2C6H5

184.24

6, 675

54

312

HOC6H4CH2C6H5

184.24

6, 675

84

322

83–85

1.599420

15 210–213

v s alc, eth; sl s aq

subl 100 7860mm 148

226–228 29

6.6 aq; v s alc, chl, eth; s bz 60 50

misc aq, alc; sl s eth s alc, eth; sl s aq v s alc, chl, alk, HOAc

60 v s alc, eth; i bz, chl

⬎110

s organic solvents, alk s hot aq, org solvents, HOAc, alkalis

INTERACTIVE

h100

Formula

ROTATED

Name

LEFT

No.

h119 h120 h121 h122 h123 h124

h125 h126

1.239

h127 h128 h129

2-(2-Hydroxyethoxy)phenol N-(2-Hydroxyethyl)acetamide 2-Hydroxyethyl acetate 2-Hydroxyethyl acrylate 3-(1-Hydroxyethyl)aniline 2-Hydroxyethyl disulfide N-(2-Hydroxyethyl)ethylenediamineN,N,N⬘-triacetic acid 2-Hydroxyethylhydrazine 2-Hydroxyethyl methacrylate N-(2-Hydroxyethyl)morpholine N-(2-Hydroxyethyl)phthalimide 1-(2-Hydroxyethyl)piperazine

HOCH2CH2C6H4OH

154.17

62, 782

HOCH2CH2NHC("O)CH3

103.12

41, 430

CH3CO2CH2CH2OH H2C"CHCO2CH2CH2OH

104.11 116.12

2, 141 24, 1469

CH3CH(OH)C6H4NH2

137.18

133, 1654

HOCH2CH2SSCH2CH2OH

154.25

1, 471

HO2CCH2N(CH2CH2OH)CH2CH2N(CH2CO2H)2

278.26

HOCH2CH2NHNH2

76.10

HOCH2CH2O2CC(CH3)"CH2

15

1.108 1.011

1.457520

1280.7mm

63–65

1555mm

176

misc aq; sl s bz

188 9212mm

88 98

misc aq, alc, chl, eth

1583.5mm

⬎110

220

73

20

1.4201 1.450020 66–69

1.261

1.565520

25–27 212 dec

41, 562

130.14 131.18

27, 7

191.19

21, 469

130.19

232, 6

⫺70

1.123

1.496120

1.073

1.452020

673.5mm

97

1.083

1.476020

227

99

246

⬎110

misc aq; s alc

misc aq

126–128 1.061

Hydroxyethanal, h87 3-(␣-Hydroxyethyl)aniline, a256 N-(2-Hydroxyethyl)-3-aza-1,5-pentanediol, t266

1.506520

N-(2-Hydroxyethyl)ethyleneimine, a311 N-(2-Hydroxyethyl)piperidine, p182 2-(2-Hydroxyethyl)piperidine, p183

RIGHT

m-Hydroxybenzotrifluoride, t304 Hydroxybutanedioic acids, h186, h187 5-Hydroxydecanoic acid, ␦-lactone, d17

1.123320 20

99–100

DEAN 37261 (McGHP)

h118

ROTATED

h104

h105

h111

h127

h128

h129

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

N-(2-Hydroxyethyl)piperazine-N⬘ethane-sulfonic acid N-(2-Hydroxyethyl)piperidine N-(2-Hydroxyethyl)pyridine N-(2-Hydroxyethyl)pyrrolidine N-(2-Hydroxyethyl)2-pyrrolidinone 2-Hydroxyethyl salicylate (2-Hydroxyethyl)triphenylphosphonium bromide 8-Hydroxy-7-iodo-5quinolinesulfonic acid 2-Hydroxyisobutyric acid 2-Hydroxyisobutyronitrile Hydroxylamine HCl 4-Hydroxy-2-mercapto6-methylpyrimidine 4-Hydroxy-2-mercapto6-propylpyrimidine 4-Hydroxy-3-methoxybenzaldehyde 4-Hydroxy-3-methoxybenzoic acid

h131 h132 h133 h134

1.240

h135 h136

h137

h138 h138a h139 h140 h141 h142 h143

Beilstein reference

238.31

Merck: 12, 4687

129.20

20, 25

1.005915 4

1.480420

199–202

68

HOCH2CH2NC5H4

123.16

21, 50

1.093

1.536820

1169mm

92

HOCH2CH2NC4H8

115.8

202, 5

0.985

1.471320

8113mm

56

129.16

214, 3142

1.143

1.496020

1422mm

⬎110

(HO)C6H4CO2CH2CH2OH

182.18

10, 81

1.224

1.548020

16613mm

⬎110

HOCH2CH2P(C6H5)3Br

387.26

16, 761

217–219

351.12

22, 408

269–270 dec

104.11

3, 313

82

841.5mm

85.11

3, 316

⫺19

8223mm

69.49 142.18

24, 351

(CH3)2C(OH)CO2H (CH3)2C(OH)CN H2NOH · HCl

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

0.932

170.23

1.399020

159 dec 330 dec 219–221

152.15

8, 247

CH3OC6H3(OH)CO2H

168.15

10, 392

1.056

80–81 210–213

Solubility in 100 parts solvent sat’d aq: 2.25M 0

234 dec

1.670

CH3OC6H3(OH)CHO

Flash point,⬚C

285

v s aq, alc, chl

v s aq, alc, eth 63

v s aq NH3, alkalis; sl s alc, acet 0.1 aq; 1.7 alc; 1.7 acet; v s alkalis 1 aq; s alc, chl, pyr 0.12 aq; v s alc

INTERACTIVE

h130

Formula weight

Formula

ROTATED

Name

LEFT

No.

h145 h146 h147 h148 h149 h150 h151

2-Hydroxy-4-methoxybenzophenone 4-Hydroxy-3-methoxybenzyl alcohol N-(Hydroxymethyl)acrylamide 4-Hydroxy-3-methyl2-butanone 7-Hydroxy-4-methylcoumarin N-(Hydroxymethyl)nicotinamide 4-Hydroxy-4-methyl2-pentanone N-(Hydroxymethyl)phthalimide

CH3OC6H3(OH)C("O)C6H5

228.25

8, 312

63–66

CH3OC6H3(OH)CH2OH

154.17

6, 1113 4

101.11

2 , 1472

1.074

1.430

HOCH2CH(CH3)C("O)CH3

102.13

11, 422

0.993

1.434020

176.17

18, 31

190–192

(C5H4N)C("O)NHCH2OH

152.15

10, 4750

152–154

(CH3)2C(OH)CH2C("O)CH3

116.16

Merck: 12, 3008 21, 475

1.241

Hydroxyhydroquinone, b34 2-Hydroxyisobutyronitrile, h153

0.930625 4

1.423520

none 9215mm

⫺44

h134

167.91

58

misc aq sl s aq, alc, bz

1,3-Hydroxy-2-methyl-2-propylamine, a226

h137

h140

RIGHT

h131

81 s alc, HOAc; sl s eth

147–149

2-Hydroxy-3-methyl-2-cyclopenten-1-one, m223 (2-Hydroxymethyl)-2-nitro-1,3-propanediol, t442

h130

v s alc, chl, eth

113–115 20

H2C"CHC("O)NHCH2OH

177.16

1605mm

DEAN 37261 (McGHP)

h144

ROTATED

h141

h148

h151

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

4-Hydroxy-N-methylpiperidine 2-Hydroxy-2-methylpropionitrile 2-Hydroxy-2-methylpropiophenone 5-Hydroxy-2-methylpyridine 3-Hydroxy-2-methyl4-pyrone 2-Hydroxy-1-naphthaldehyde 1-Hydroxy-2-naphthoic acid 2-Hydroxy-1-naphthoic acid 3-Hydroxy-2-naphthoic acid 2-Hydroxy-1,4naphthoquinone 4-Hydroxy-3-nitrobenzenearsonic acid 4-Hydroxy-3-nitrobenzoic acid 5-Hydroxy-2pentanone 4-Hydroxyphenylacetic acid 4-(4-Hydroxyphenyl)2-butanone 4-Hydroxyphenylglycine

h153 h154 h155 h156 h157

1.242

h158 h159 h160 h161 h162 h163 h164 h165 h166 h167

Formula weight 115.18

Beilstein reference

Density, g/mL

211, 188

Refractive index

Boiling point,⬚C

Flash point,⬚C

1.477520

29–31

200

⫺19

95

63

1034mm

⬎110

85.10

3, 316

0.926725 4

1.399220

C6H5C("O)C(CH3)2OH

164.20

81, 553

1.077

1.533020

HO(C5H2N)CH3

109.13

213, 480

(CH3)2C(OH)CN

Melting point,⬚C

Solubility in 100 parts solvent

s aq, alc, chl, eth

168–170

126.11

161–162

1.2 aq; v s hot aq; s alc, alk; sl s bz, eth 19227mm

C10H6(OH)CHO

172.18

8, 143

82–85

C10H6(OH)CO2H

188.18

10, 331

191–192

C10H6(OH)CO2H

188.18

10, 328

167 dec

C10H6(OH)CO2H

188.18

10, 333

222–223

v s alc, eth; s bz, chl

174.16

8, 300

dec ⬎191

s HOAc

HOC6H3(NO2)AsO(OH)2

263.04

161, 456

⬎300

v s alc, acet, HOAc, alk; sl s aq; i eth

HOC6H3(NO2)CO2H

183.12

10, 181

184–185

CH3C("O)CH2CH2CH2OH

102.13

1, 831

HOC6H4CH2CO2H

152.15

10, 190

149–151

HOC6H4CH2CH2C("O)CH3

164.20

82, 117

82–83

HOC6H4CH(NH2)CO2H

167.16

141, 659

240 dec

1.00720 4

1.437220

v s alc, bz, eth, alk

144100mm

93

misc aq; s alc, eth v s alc, eth; sl s aq

sl s aq, alc, bz, acet

INTERACTIVE

h152

Formula

ROTATED

Name

LEFT

No.

h169 h170 h171 h172 h173 h174 h175 h176

1.243

h177 h178 h179 h180 h181

N-(4-Hydroxyphenyl)glycine 2⬘-Hydroxy-3-phenylpropiophenone 1-(3-Hydroxyphenyl)urea N-Hydroxyphthalimide 2-Hydroxypropionitrile 3-Hydroxypropionitrile

HOC6H4NHCH2CO2H

167.16

13, 488

HOC6H4C("O)CH2CH2C6H5

226.28

82, 202

HOC6H4NHC("O)NH2

152.15

13, 417

CH3CH(OH)CN HOCH2CH2CN

163.13 71.08 71.08

21, 500 32, 209 3, 298

0.983425 1.040425 4

1.402725 1.424820

2⬘-Hydroxypropiophenone 4⬘-Hydroxypropiophenone 1-(2-Hydroxy-1propoxy)-2-propanol Hydroxypropyl acrylate Hydroxypropyl methacrylate 2-Hydroxypyridine 3-Hydroxypyridine 4-Hydroxypyridine

HOC6H4C("O)CH2CH3

150.18

8, 102

1.094

1.548020

HOC6H4C("O)CH2CH3

150.18

8, 102

CH3CH(OH)CH2OCH2CH(OH)CH3

134.18

H2C"CHCO2(CH2)3OH H2C"C(CH3)CO2(CH2)3OH

130.14 144.17

HOC5H4N HOC5H4N HOC5H4N

95.10 95.10 95.18

24, 1469 24, 1532

244 dec 1.596820

⬎110

36–37 182–184 233 dec ⫺40 ⫺46

10350mm 221

76 129

11515mm

⬎110

148 1.444020

231.8

138

1.044 1.066

1.445020 1.447020

775mm 570.5mm

89 96

21, 43

misc aq, alc; s eth misc aq, alc, acet; 2,3 eth; i bz, PE v s alc, eth; sl s aq v s alc, eth; sl s aq

1.025220 20

105–107 126–129

280–281 1513mm 23012mm

misc aq, alc

aq, alc, bz, sl s eth v s aq, alc; sl s eth v s aq; i alc, bz, eth

1-Hydroxy-2-propanone, h90 3-Hydroxypropionitrile, c323 1-(2-Hydroxy-1-propoxy)-2-propanol, b204 3-Hydroxy-1-propyne, p249

RIGHT

␣-Hydroxy-␣-phenylacetophenone, b46 3-(p-Hydroxyphenyl)alanine, t455 2-Hydroxy-2-phenylbenzeneacetic acid, b37 3-Hydroxy-1-propanesulfonic acid ␥-sultone, p197 2-Hydroxypropanoic acid, L1, L2

1-Hydroxy-2-naphthalenecarboxylic acid, h158 2-Hydroxy-1-naphthalenecarboxylic acid, h159 3-Hydroxy-2-naphthalenecarboxylic acid, h160 6-Hydroxynicotinic acid, h182 Hydroxynitroanilines, a238, a239, a240

s alk, acid; v sl s aq, alc, acet, bz, eth

DEAN 37261 (McGHP)

h168

ROTATED

h152

h156

h161

h171

INTERACTIVE

No.

Name

h182

2-Hydroxypyridine-5carboxylic acid 3-Hydroxypyridine-Noxide 8-Hydroxyquinoline 8-Hydroxyquinoline-5sulfonic acid DL-Hydroxysuccinic acid

h183 h184 h185 h186

1.244

h188 i1 i2 i3 i4

N-Hydroxysuccinimide Icosane 1-Icosene 1H-Imidazole 2-Imidazolidinethione

i5 i6

2-Imidazolidone 3,3⬘-Iminobis(N,N-dimethyl)propylamine Iminodiacetic acid Iminodiacetonitrile Iminodibenzyl Indane

i7 i8 i9 i10 i11 i12 i13

139.11

(HO)C5H4N"O

111.10

Density, g/mL

Refractive index

Melting point,⬚C

72–74 ⬎300

HO2CCH(OH)CH2CO2H

134.09

3, 435

131–133

HO2CCH(OH)CH2CO2H

134.09

3, 419

100

115.09 282.56 280.54 68.08 102.16

21, 380 1, 174 13, 881 23, 45 24,4

86.09 187.33

24, 16 43, 565

133.10 95.11 195.27 118.18

4, 365 4, 367

HO2CCH2NHCH2CO2H NCCH2NHCH2CN

134.18 132.16 178.14 116.16 117.15 175.19

Solubility in 100 parts solvent sl s aq, alc, eth

190–192 21, 91 22, 407

HN[(CH2)3N(CH3)2]2

Flash point,⬚C

⬎300

22, 215

145.16 225.22

CH3(CH2)18CH3 CH3(CH2)17CH"CH2

Boiling point,⬚C

Merck: 12, 4966 6, 575 7, 360 Merck: 12, 6645 5, 515 20, 304 22, 66

0.777737

1.434640

95–98 36.4 28.7 90–91 203–204

1.449020

133–135 ⫺78

0.963920 4

1.538320

243 dec 77 105–108 ⫺51.4

1.109045 4

1.56145

0.996820 4 1.0643

1.576220 1.60960

0.841

267742mm

v s alc, acet, bz, chl v s aq; sl s alc, eth 56 aq; 45 EtOH; 18 acet; 0.8 eth; 23 diox 36 aq; 87 EtOH; 61 acet; 2.7 eth; 75 diox v s aq

343.8 342.4 257

⬎112

13120mm

98

145

v s aq, alc, chl, eth 2 aq; s alc, pyr; i bz, acet, chl, eth v s aq, hot alc

2 aq; v sl s bz, eth s aq, alc; sl s eth 178

50

s alc, chl, eth; i aq

51–53 40–42 dec 241

255 243–245

⬎110 111

v s alc, eth; sl s aq s alc, eth; sl s aq v s aq; s alc

⫺1.8 52.54 168–170

181.6 253–254

58 ⬎110

misc alc, bz, chl, eth s hot aq, bz, eth v s alc; s acet, eth

INTERACTIVE

i14 i15 i16

5-Indanol 1-Indanone 1,2,3-Indantrione hydrate Indene Indole Indole-3-acetic acid

HO(C5H3N)CO2H

Beilstein reference

ROTATED

(⫺)-Hydroxysuccinic acid

Formula weight

LEFT

h187

Formula

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Indole-2,3-dione Indoline Inositol Iodoacetamide Iodoacetic acid

147.13 119.17 180.16 184.96 185.95

ICH2CONH2 ICH2CO2H

Icosane, e1 Imidodicarbonic diamide, b238 Imidole, p279

21, 432 20, 257 62, 1157 2, 223 2, 222

203.5 dec 1.063 1.752

1.590620

221 225 93–96 79–82

Indalone, b450 Indanamine, a195, a196

1.245

h184

h185

i11

Indonaphthene, i14 5-Iodoanthranilic acid, a199

i3

i4

i12

i5

i13

i9

RIGHT

i10

h188

s hot aq, hot alc, alk sl s aq 14 aq; sl s alc; i eth s hot aq s aq, alc; v sl s eth

92

DEAN 37261 (McGHP)

i17 i18 i19 i20 i21

i14

ROTATED

i15

i16

i17

i18

i19

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

1.246

219.03 204.01 322.10 248.02 184.02 184.02 210.06 268.19 296.24 155.97

12, 670 5, 215 5, 218 9, 363 1, 123 1, 123 52, 13 1, 168 11, 67 1, 96

1.821 1.830820

1.682020 1.620020

2.24925 4 1.615420 1.592020 1.62615 15 1.25720 4 1.201 1.935820

1.499920 1.499120 1.547220 1.485020 1.4844 1.513020

i32 i33

2-Iodoethanol Iodoform

ICH2CH2OH CHI3

171.97 393.73

1, 339 1, 73

2.219720 4 4.008

1.569420

i34 i35 i36 i37 i38

1-Iodoheptane 1-Iodohexadecane 1-Iodohexane 1-Iodomethane 1-Iodo-2-methylpropane 2-Iodo-2-methylpropane 1-Iodo-3-nitrobenzene 1-Iodo-4-nitrobenzene 1-Iodononane 1-Iodooctadecane 1-Iodooctane 1-Iodopentane 1-Iodopropane 2-Iodopropane 3-Iodo-1-propene 5-Iodosalicylic acid

CH3(CH2)6I CH3(CH2)15I CH3(CH2)5I CH3I (CH3)2CHCH2I

226.10 352.35 212.08 141.94 184.02

1, 155 1, 172 1, 146 1, 69 1, 128

1.37320 4 1.121 1.43720 4 2.278920 4 1.603520

1.490020 1.480620 1.492020 1.530820 1.496020

⫺48 23

(CH3)3CI

184.02

13, 326

1.57100

1.491820

IC6H4NO2 IC6H4NO2 CH3(CH2)8I CH3(CH2)17I CH3(CH2)7I CH3(CH2)4I CH3CH2CH2I (CH3)2CHI ICH2CH"CH2 IC6H3(OH)CO2H

249.01 249.01 254.18 380.40 240.13 198.06 169.99 169.99 167.97 264.02

5, 253 5, 252 1, 166 1, 173 1, 160 1, 133 1, 113 1, 114 1, 202 10, 112

1.947750 4

i39 i40 i41 i42 i43 i44 i47 i48 i49 i50 i51

25 ⫺31 163–165 162–164 ⫺103.5 ⫺104.0

⫺3 ⫺111

14615mm 188

⬎110 74

130–131 120 180 13215mm 16015mm 72.4

33 23

1.487020

1.33020 4 1.51220 4 1.748920 1.704220 1.84522 4

1.488920 1.495420 1.505820 1.499220 1.554021

s alc, eth; sl s aq i aq; s alc, eth i aq; s alc, eth i aq; s eth i aq; s alc, eth 0.4 aq; misc alc, bz, chl, eth s aq; v s alc, eth 1.4 alc; 10 chl; 13 eth; v s bz, acet i aq; s alc, eth

755mm

65 none

⫺66.5 ⫺93.5

204 20710mm 179–180 42.5 121

78 ⬎110 61 none 12

⫺38

100

7

dec aq; misc alc, eth

36–38 175–177

280 289772mm 1088mm 1972mm 226 155 102 89.5 103

71 ⬎110 85 ⬎110 95 51 44 42 18

i aq; s alc, eth

120–123

1.288

⬎110 ⬎110 none

i aq; s alc, eth misc alc, chl, eth

33–35 ⫺46 ⫺85 ⫺101 ⫺90 ⫺99 189–191

i aq 1.4 aq; misc alc, eth i aq; misc alc, eth

s alc, eth sl s aq; s alc, eth 0.1 aq; misc alc, eth 0.14 aq; misc alc, eth misc alc, chl, eth v s alc; i bz, chl

INTERACTIVE

IC6H4NH2 C6H5I C6H5I(O2CCH3)2 IC6H4CO2H HC3CH2CH2CH2I CH3CH2CH(I)CH3 C6H11I CH3(CH2)9I CH3(CH2)11I CH3CH2I

Solubility in 100 parts solvent

ROTATED

3-Iodoaniline Iodobenzene Iodobenzene diacetate 2-Iodobenzoic acid 1-Iodobutane 2-Iodobutane Iodocyclohexane 1-Iododecane 2-Iodododecane Iodoethane

Flash point,⬚C

LEFT

i22 i23 i24 i25 i26 i27 i28 i29 i30 i31

Boiling point,⬚C

2-Iodothiophene 2-Iodotoluene 3-Iodotoluene 4-Iodotoluene Iodotrimethylsilane 1-Iodoundecane ␣-Ionone ␤-Ionone Isatoic anhydride D-(⫺)-Isoascorbic acid DL-Isoborneol Isobutyl acetate Isobutyl acetoacetate Isobutyl acrylate Isobutylamine Isobutylbenzene Isobutyl chloroformate Isobutyl formate Isobutyl isobutyrate Isobutyl methacrylate

IC6H4CH3 IC6H4CH3 IC6H4CH3 (CH3)3SiI CH3(CH2)10I

(CH3)2CHCH2O2CCH3 CH3COCH2CO2CH2CH(CH3)2 H2C"CHCO2CH2CH(CH3)2 (CH3)2CHCH2NH2 C6H5CH2CH(CH3)2 ClCO2CH2CH(CH3)2 HCO2CH2CH(CH3)2 (CH3)2CHCH2O2CH(CH3)2 H2C"C(CH3)CO2CH2CH(CH3)2

210.04 218.04 218.04 218.04 200.10 282.21 192.30 192.30 163.13 176.12 154.25 116.16 158.20 128.19 73.14 134.22 136.58 102.13 144.22 142.19

17, 34 5, 310 5, 311 5, 312 11, 66 7, 168 7, 167 27, 264 62, 80 2, 131 23, 1227 4, 163 5, 414 3, 12 2, 21 2, 291 23, 1287

1.902 1.713 1.698

1.652020 1.607920 1.604020

1.40620 4 1.220 0.93220 0.94617

1.471020 1.484920 1.498020 1.52117

34–36

0.871220 0.980 0.890 0.72420 4 0.853220 1.053 0.877620 0.854220 0.88225 15

1.390220 1.424020 1.4140 1.397220 1.486620 1.407020 1.385520 1.399920 1.417025

1,3-Isobenzofurandione, p169 Isobutane, m390 Isobutene, m399 ␣-Isobutoxy-␣-phenylacetophenone, b48 Isobutylacetylene, m372 Isobutyl alcohol, m397

233 dec 169 dec 214 subl ⫺99

⫺86.6 ⫺51.5 ⫺95.5 ⫺80.7

7315mm 211 8210mm 211 106 1305mm 12411mm 12812mm

71 90 82 90 ⫺31 ⬎110 104 ⬎110

116.5 10022mm 132 68 172.8 128.8 98.4 148.5 155

18 78 32 ⫺9 55 27 10 38 41

v s eth i aq; s alc, eth i aq; misc alc, eth

s alc, bz, chl, eth s alc, bz, chl, eth sl s aq, hot alc, acet s aq, alc, acet, pyr v s alc, chl, eth 0.7 aq; v s alc

misc aq, alc, acet, eth misc alc, eth misc bz, chl, eth 1 aq; misc alc, eth 0.5 aq; misc alc misc alc, eth

Isobutyl bromide, b371 Isobutyl chloride, c179 Isobutyl chlorocarbonate, i68 Isobutyl ether, d458 Isobutyl mercaptan, m395 Isobutyl methyl ketone, m370

RIGHT

Isatin, i17 Isoamyl acetate, i91 Isoamyl alcohol, m163 sec-Isoamyl alcohol, m164 Isoamyl bromide, b362 Isoamyl chloride, c169a Isoamyl nitrite, i92

⫺40

DEAN 37261 (McGHP)

1.247

i52 i53 i54 i55 i56 i57 i58 i59 i60 i61 i62 i63 i64 i65 i66 i67 i68 i69 i70 i71

ROTATED

i52

i58

i59

i60

i61

i62

INTERACTIVE

No. i72 i73 i74 i75 i76

Name

Formula

Formula weight

178.30

(CH3)2CHCH2OCH"CH2 (CH3)2CHCHO

100.16 72.11

i80 i81

Isobutyramide Isobutyric acid

(CH3)2CHCONH2 (CH3)2CHCO2H

i82 i83 i84 i85 i86 i87 i88 i89 i90

Isobutyric anhydride Isobutyronitrile Isobutyrophenone Isobutyryl chloride Isodecyl acrylate Isodecyl methacrylate L-Isoleucine Isooctyl acrylate Isooctyl diphenyl phosphite Isopentyl acetate Isopentyl nitrite Isophorone Isophorone diisocyanate Isopropenyl acetate 3-Isopropenyl-␣,␣-dimethylbenzyl isocyanate 2-Isopropoxyethanol

1.248

i91 i92 i93 i94 i95 i96

i97

1.01520 4 0.87022 4 0.88804

1.402820 1.371522 1.397420

0.880

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

123 67 137

21 ⫺21 26

1.40020

190–191

60

0.930

1.396020

137

39

13, 1862 1, 671

0.770220 20 0.798820 4

1.395020 1.372320

⫺112 ⫺65.9

83.4 64.5

⫺13 ⫺18 (CC)

0.2 aq 11 aq; misc alc, bz, acet, chl, eth

87.12 88.11

2, 293 2, 288

1.013 0.968120

1.392520

127–129 ⫺46

216–220 154

56

17 aq; misc alc, chl, eth

[(CH3)2CHCO]2O (CH3)2CHCN C6H5COCH(CH3)2 (CH3)2CHCOCl H2C"CHCO2C10H21 H2C"C(CH3)CO2C10H21 C2H5CH(CH3)CH(NH2)CO2H H2C"CHCO2C8H17 (C6H5O)2POC8H17

158.20 69.11 148.21 106.55 212.34 226.36 131.18 184.25 346.41

2, 292 2, 294 7, 316 2, 293

0.954 0.770420 0.98820 1.017 0.875 0.878

1.406220 1.372020 1.5172 1.407320 1.442020 1.443020

⫺56 ⫺71.5

59 8 84 1 106 ⬎110

0.880 1.045

1.437020 1.522020

182 104 217 91–93 12110mm 12610mm subl 168 12520mm 188

CH3CO2CH2CH2CH(CH3)2 ONOCH2CH2CH(CH3)2

130.19 117.15 138.21 222.29

2, 132 1, 402 7, 65

0.87615 4 0.872 0.95520 1.049

1.400720 1.386020 1.475920 1.484120

142 99 215.2 15915mm

25 10 84 ⬎110

CH3CO2C(CH3)"CH2 H2C"C(CH3)C6H4C(CH3)2NCO

100.12 201.27

22, 278

0.909 1.108

1.400520 1.530020

94 268–271

18 ⬎110

(CH3)2CHOCH2CH2OH

104.15

12, 519

0.903

1.410420

4413mm

45

4, 454

⫺71 ca. 20

⫺90

288 dec

⫺78.5 ⫺8.1

i aq; misc alc, eth misc alc; sl s aq (dec) i aq; misc alc

v s alc, eth; sl s aq dec aq, dec alc; s eth

4 aq; sl s hot alc 80

0.25 aq; misc alc, eth misc alc, eth; sl s aq 1.2 aq

INTERACTIVE

(CH3)2CHCH2Si(OCH3)3

i77

1, 377 1, 377 2, 241

Refractive index

ROTATED

119.12 103.12 130.19 340.57 220.39

Density, g/mL

LEFT

(CH3)2CHCH2ONO2 (CH3)2CHCH2ONO C2H5CO2CH2CH(CH3)2 CH3(CH2)16CO2CH2CH(CH3)2 (CH3)2CHCH2Si(OC2H5)3

i78 i79

Isobutyl nitrate Isobutyl nitrite Isobutyl propionate Isobutyl stearate Isobutyltriethoxysilane Isobutyltrimethoxysilane Isobutyl vinyl ether Isobutyraldehyde

Beilstein reference

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

i99 i100 i101 i102 i103 i104 i105 i106 i107 i108

3-Isopropoxypropylamine Isopropyl acetate Isopropylamine 2-Isopropylaniline 4-Isopropylbenzaldehyde Isopropylbenzene 4-Isopropylbenzyl alcohol N-Isopropylbenzylamine Isopropyl butyrate Isopropyl chloroacetate Isopropylcyclohexane

(CH3)2CHO(CH2)3NH2

117.19

43, 739

0.845

1.419520

(CH3)2CHO2CCH3 (CH3)2CHNH2 (CH3)2CHC6H4NH2 (CH3)2CHC6H4CHO

102.13 59.11 135.2 148.21

2, 130 4, 152 12, 1147 7, 318

0.871820 0.68625 4 0.955 0.977

1.377020 1.371125 1.547720 1.529820

(CH3)2CHC6H5 (CH3)2CHC6H4CH2OH

120.20 150.22

5, 393 6, 543

0.86420 4 0.98215

1.491520 1.520620

C6H5CH2NHCH(CH3)2

149.24

0.892

CH3CH2CH2CO2CH(CH3)2 ClCH2CO2CH(CH3)2

130.19 136.58

2, 271 2, 198

C6H11CH(CH3)2

126.24

5, 41

1.249

39

⫺73 ⫺95

89 31.7 222 236

2 ⫺37 95 93

3 aq; misc alc, eth misc aq, alc, eth

⫺96 28

152–154 248.4

36 ⬎110

s alc, bz, eth misc alc, eth; i aq

1.502520

200

87

0.859 1.096

1.393220 1.419020

131 149–150

30 70

0.802320 4

1.439920

155

35

Isonicotinaldehyde, p263 Isonicotinic acid, p267 Isonicotinonitrile, c330 Isooctane, t381 Isopentane, m158 Isopentyl alcohol, m163 Isopentyl isopentanoate, m177 Isopentyl isovalerate, m177 Isophorone, t364 Isophthalic acid, b17 Isophthalonitrile, d283 Isophthaloyl dichloride, b15 Isoprene, m157

⫺90

Isopropanolamine, a263 Isopropenyl acetate, p207 Isopropenylacetylene, m174 Isopropenyl methyl ether, m106 Isopropylacetylene, m178 Isopropylacrylic acid, m369 Isopropyl alcohol, p202 Isopropyl bromide, b401 Isopropyl chloride, c226 Isopropyl cyanide, i83 Isopropylethanol, m164 Isopropyl ether, d476 Isopropylethylene, m167

v s alc, eth

RIGHT

Isobutyl octadecanoate, i75 Isobutyraldehyde, m389 Isobutyric acid, m402 Isocapronitrile, m361 Isocinchomeronic acid, p269 Isocrotonic acid, b483 Isocumene, p225 5-Isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane, i94 Isodurene, t98 Isoeugenol, m108 Isohexane, m357 Isoleucinol, a211 Isomesityl oxide, m370

7985mm

DEAN 37261 (McGHP)

i98

ROTATED

i93

i94

INTERACTIVE

No. i109 i110

i111

i112 i113

1.250

i114 i115 i116 i117 i118

i120 i121

i123 i124 i125

1-Isopropyl-4-nitrobenzene

Beilstein reference 22, 336

CH3(CH2)14CO2CH(CH3)2

298.51

(CH3)2C[C6H2(Br)2OCH2CH2OH]2

632.01

[(C10H21O)2POC6H4]2C(CH3)2

917.34

(CH3)2C(C6H10OH)2

240.39

62, 761

(CH3)2C(C6H4OH)2

228.29

6, 1011

(CH3)2CHCNO (CH3)2CHO2CCH(OH)CH3 (CH3)2CHC6H3(CH3)NH2

110.16 85.11 132.16 149.24

23, 83 4, 155 3, 282

(CH3)2CHC6H4CH3

134.21

(CH3)2CHC6H4CH3

Density, g/mL

Refractive index

0.862

1.438520

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

⬎110 107

0.964

1.498020

336

⬎110

23414mm

⬎110

137–140

2204mm

129–131

256–260 74–75 166–168

⫺2 57 41

0.866 0.99820 20 0.957

1.382520 1.408225 1.544020

5, 419

0.876620 4

1.500620

⫺71.5

178.2

misc alc, eth

134.21

5, 419

0.861020 4

1.493020

⫺63.8

175.1

misc alc, eth

(CH3)2CHC6H4CH3

134.21

5, 420

0.857320 4

1.490920

⫺68.9

177.1

(CH3)2CHC6H3(CH3)OH

150.22

6, 532

0.92580 4

51.5

232.5

(CH3)2CHC6H3(CH3)OH

150.22

62, 491

111–114

(CH3)2CHC6H3(CH3)OH

150.22

6, 526

51

(CH3)2CHONO2 (CH3)2CHONO

105.09 89.09

(CH3)2CHC6H4NO2

165.19

1, 363 Merck: 12, 5235 52, 308

47

s aq, alc, eth

misc alc, eth i aq; v s alc, chl, eth

⬎110

1.03619 19 0.84425 4

1.39120 1.352020

102 39752mm

12

1.090

1.538020

10711mm

⬎110

INTERACTIVE

i126

Formula weight

ROTATED

i122

Isopropyl hexadecanoate 4,4⬘-Isopropylidenebis(2,6-dibromophenoxy)ethanol 4,4⬘-Isopropylidenebis(diisodecyl phenyl phosphite) 4,4⬘-Isopropylidenedicyclohexanol 4,4⬘-Isopropylidenediphenol 2-Isopropylimidazole Isopropyl isocyanate Isopropyl S-(⫺)-lactate 2-Isopropyl-6-methylaniline 2-Isopropyl-1-methylbenzene 3-Isopropyl-1-methylbenzene 4-Isopropyl-1-methylbenzene 2-Isopropyl-5-methylphenol 4-Isopropyl-3-methylphenol 5-Isopropyl-3-methylphenol Isopropyl nitrate Isopropyl nitrite

Formula

LEFT

i119

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

2-Isopropylphenol 3-Isopropylphenol 4-Isopropylphenol 4-Isopropylpyridine Isopropyl tetradecanoate

i132 i133 k1 k2

Isopulegol Isoquinoline Ketene 8-Ketotricyclo[5.2.1.02,6]decane DL-Lactic acid L-(⫹)-Lactic acid ␣-Lactose

L1 L2 L3

(CH3)2CHC6H4OH (CH3)2CHC6H4OH (CH3)2CHC6H4OH (CH3)2CH(C5H4N) (CH3)2CHO2C(CH2)12CH3

H2C"C"O

CH3CH(OH)CO2H CH3CH(OH)CO2H

136.19 136.19 136.19 121.18 270.46

6, 504 6, 505 6, 505 20, 248 23, 923

1.01220 0.994 0.99020 0.938 0.850

1.525920 1.525020

154.25 129.16 42.04 150.22

6, 65 20, 380 1, 724 72, 133

0.912 1.091030 4

1.472520 1.620830

1.063

1.502020

90.08 90.08 342.32

3, 268 3, 261 31, 408

1.24915 4 1.206025 4

1.427020

1.498020 1.435020

1.251

Isopropyl myristate, i131 Isopropyl palmitate, i109 Isopropyltoluenes, i118, i119, i120 Isopseudocumenol, t385 Isovaleraldehyde, m181 Isovaleric acid, m184 Isovaleronitrile, m185

Isopropylidone acetone, m370 Isopropyl iodide, i49 Isopropyl mercaptan, p199 1-Isopropyl-4-methyl-1,3-cyclohexadiene, t10 2-Isopropyl-5-methylcyclohexanol, m12 1-Isopropyl-4-methyl-1,4-cyclohexadiene, t11 Isopropyl methyl ketone, m165

15–16 25 59–61 ca. 3

26.5 ⫺151

16.8 53 202

212–213 228 212 173 19320mm

88 104

misc alc, eth 316 alc; 350 eth

66 ⬎110

9112mm 243.5 ⫺49.8 13230mm

78 107

12214mm 11912mm

⬎110 ⬎110

s caster oil, cottonseed oil, acet, EtOAc, EtOH, toluene, mineral oil v sl s aq sl s aq; s acid s acet, eth; dec aq

101

DEAN 37261 (McGHP)

i127 i128 i129 i130 i131

s aq, alc; i chl, PE v s aq, alc, eth 20 aq; v sl s alc

Isovaleryl chloride, m186 Itaconic acid, m253 Keto-, see oxo2-Ketobutyric acid, o60 5-Keto-1,7,7-trimethylnorcamphane, c3 4-Ketovaleric acid, o63 Lactonitrile, h172

RIGHT ROTATED

i114

i132

i133

k2

L3

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

1.252

R-(⫹)-Limonene S-(⫺)-Limonene (⫹)-Limonene oxide Linalool Linalyl acetate S-(⫹)-Lysine Maleic acid

m2

Maleic anhydride

m3

Malonic acid

m4 m5 m6 m7 m8 m9 m10 m11 m12 m13 m14

Malonodiamide Malononitrile Malonyl dichloride D-(⫹)-Maltose hydrate DL-Mandelic acid Mandelonitrile Mannitol D-(⫹)-Mannose (⫺)-Menthol (⫺)-Menthone S-(⫹)-Menthyl acetate

Density, g/mL

Refractive index

1.52520

Melting point,⬚C

(CH3)2CHCH2CH(NH2)CO2H (CH3)2CHCH2CH(NH2)CO2H

342.32 131.18 131.18

31, 408 4, 447 4, 437

H2N(CH2)4CH(NH2)CO2H HO2CH"CHCO2H

136.24 136.24 152.24 154.25 196.29 146.19 116.07

5, 133 5, 136 17, 44 1, 462 2, 141 4, 435 2, 748

1.590

212 dec 130.5

98.06

17, 432

1.48

52.8

HO2CCH2CO2H

104.06

2, 566

1.63

135–137

H2NCOCH2CONH2 NCCH2CN ClCOCH2COCl

102.09 66.06 140.95 360.32 152.15 133.15 182.17 180.16 156.27 154.25 198.31

2, 582 2, 589 21, 252 31, 386 10, 192 10, 193 1, 534 31, 284 6, 28 7, 38 6, 32

1.191020 4 1.448619 4 17 1.540 20 1.3004 1.117 1.5220 1.5420 0.89015 15 0.89520 4 1.448020

C6H5CH(OH)CO2H C6H5CH(OH)CN

202 dec 332 293 dec

1.29318 0.841120 4 0.84120 4 0.929 0.86515 0.89520 4

1.4730 1.474620 1.466120 1.461520 1.446020

1.414634 1.462020

1.531520

1.45825 1.451020

⫺96.5 ⫺96.5

172–175 32–34 119–121 120–122 ⫺10 166–168 128–130 41–43 ⫺6

Boiling point,⬚C

Flash point,⬚C

subl 293 subl 145 178 178 11450mm 197720mm 220

49 48 65 76 90

202

103

220 5519mm dec 130

112 47

170 2903.5mm

97

212 207 229–230

93 72 77

Solubility in 100 parts solvent 45 aq; i alc, eth 1 aq; 0.13 alc; i eth 2.4 aq25; 0.07 alc; 1 HOAc; i eth misc alc, eth misc alc, eth misc alc, eth misc alc, eth v s aq; sl s alc; i eth 70 aq; 70 alc; s acet, HOAc; sl s eth s aq (to acid), alc (to ester); 227 acet; 53 chl; 50 bz; 112 EtOAc 154 aq; 42 alc; 8 eth; 14 pyr 9 aq; i alc, eth 13 aq, 40 alc; 20 eth dec hot aq; s eth v s aq; sl s alc; i eth 16 aq; 100 alc; s eth v s alc, cho, eth; i aq 18 aq; 1.2 alc; i eth 250 aq; 28 pyr; 0.8 alc v s alc, chl, eth, PE misc alc, eth; sl s aq

INTERACTIVE

L7 L8 L9 L10 L11 L12 m1

Beilstein reference

ROTATED

␤-Lactose DL-Leucine L-Leucine

Formula weight

LEFT

L4 L5 L6

Formula

DEAN 37261 (McGHP)

Limonene, m313a Linoleic acid, o1 Linolenic acid, o7 Luminol, a151 2,6-Lupetidine, d672 ␤-Lutidine, e257 Lutidines, d685 thru d689 Maleic hydrazide, d447 Malic acid, h186, h187 Malonaldehyde bis(dimethyl acetal), t92 Malonamide nitrile, c319

Lauraldehyde, d817 Lauric acid, d809 Lauryl alcohol, d810 Laurylamine, d818 Lauryl bromide, b327 Lauryl mercaptan, d808 Lauryl methacrylate, d819 Lauryl sulfate, d820 Lepidine, m421 Leucinol, a212 Levulinic acid, o63

Malonic acid diamide, m4 Malonylurea, b1 Margaryl alcohol, h1a Mellitic acid, b20 MEM chloride, m74 Menadione, m321 1,8-Mentanediamine, d51 p-Mentha-1,8-diene, L17, L18 p-Mentha-6,8-dien-2-one, c20 Mercaptobenzene, t156

1.253 L4

L9

m10

m11

L10

L11

m2

RIGHT

L7, L8

ROTATED

m7

m12

m13

m14

INTERACTIVE

No. m15 m16 m17 m18 m19 m20 m21 m22 m23

1.254

m24

m34 m35

Beilstein reference

Density, g/mL

Refractive index

1.040 1.325

1.542020 1.503020

HSCH2CO2H

275.40 92.12 150.20

143, 885 3, 245 24, 119

HSC6H4CO2H

154.19

10, 125

167.25

27, 185

1.4220 4

HSCH2CH2OH HSCH2CH(OH)CH2OH

78.13 108.16

1, 470 1, 519

1.114320 4 1.29514 14

1.500620 1.524320

CH3CH(SH)CO2H

106.14

3, 289

1.22015 4

1.480920

HSCH2CH2CO2H

106.14

3, 299

1.218

1.491120

HS(CH2)3Si(OCH3)3

196.34

1.03920 4

1.444020

HO2CCH2CH(SH)CO2H

150.15 119.21 70.09 85.11 86.09 154.17 67.91 104.54 172.18

H2C"C(CH3)CHO H2C"C(CH3)CONH2 H2C"C(CH3)CO2H [H2C"C(CH3)CO]2O H2C"C(CH3)CN H2C"C(CH3)COCl (CH3CO2)2CHC(CH3)"CH2 CH4

3, 439 27, 140 1, 731 22, 399 2, 421 23, 1293 2, 423 22, 394 24, 292

16.04

1, 56

CH3SO3H (CH3SO2)2O

96.10 174.19

4, 4 4, 5

CH3SO2Cl

114.55

4, 5

Melting point,⬚C

⫺16.5 301–305

Boiling point,⬚C 1793mm 965mm

Flash point,⬚C ⬎110 ⬎110

165–168 180–181

0.847

1.416020

1.015320 4 1.035 0.800120 4 1.070 1.039

1.431420 1.453020 1.400720 1.442020 1.424520

Solubility in 100 parts solvent

misc aq, alc, bz, eth sl s aq; s alc v s alc, HOAc

156.9 1185mm

73 ⬎110

2 alc; 1 eth; 10 acet; 1 bz; s alk; i aq misc aq, alc, bz, eth misc alc; v s acet

10–14

10216mm

87

misc aq, alc, eth, acet

17–19

11115mm

93

198

48

5–7 105–107 ⫺81 109–111 16

dec

50 aq; 50 alc; s eth 69

⫺15

⫺15

163 8713mm 90.3 95–96 191

77 84 1.1 2 83

⫺182.5

⫺161.5

⫺35.8

6 aq; misc alc, eth s alc; sl s eth 9 aq; misc alc, eth 2.6 aq; misc acet, bz

0.7168 g/L 0.4240bp 1.481218 4

3.3 mL aq; 47 mL alc

1.430320

20 71

16710mm 13810mm

⬎110

1.5 bz; misc aq v s aq (dec)

1.480518 4

1.451820

⫺32

161

⬎110

s alc, eth

INTERACTIVE

m36

Methanesulfonic acid Methanesulfonic anhydride Methanesulfonyl chloride

Formula weight

ROTATED

m33

Menthyl anthranilate Mercaptoacetic acid 2-Mercaptobenzimidazole 2-Mercaptobenzoic acid 2-Mercaptobenzothiazole 2-Mercaptoethanol 3-Mercapto-1,2propanediol 2-Mercaptopropionic acid 3-Mercaptopropionic acid (3-Mercaptopropyl)trimethoxysilane Mercaptosuccinic acid 2-Mercaptothiazoline Methacrylaldehyde Methacrylamide Methacrylic acid Methacrylic anhydride Methacrylonitrile Methacryloyl chloride Methallylidene diacetate Methane

Formula

LEFT

m25 m26 m27 m28 m29 m30 m30a m31 m32

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Methanethiol

CH3SH

48.11

1, 288

m38

Methanol

CH3OH

32.04

1, 273

m39 m40 m41 m42 m43 m44 m45 m46

1.255

m47 m48 m49 m50

Methanol-d Methanol-d4 Methanol-13C DL-Methionine Methoxyacetic acid 2⬘-Methoxyacetophenone 3⬘-Methoxyacetophenone 4⬘-Methoxyacetophenone 3-Methoxyacrylonitrile 2-Methoxyaniline 3-Methoxyaniline 4-Methoxyaniline

3

1.966 g/L 0.791320 4 20 4

1.328420 20

⫺123

6.0

⫺97.7

64.7

11

⫺110

65.5 65.4 64

11 11 12

2.3 aq; v s alc, eth misc aq, alc, bz, chl, eth misc aq, alc, eth misc aq, alc, eth

CH3OD CD3OD1 13CH OH 3 CH3SCH2CH2CH(NH2)CO2H CH3OCH2CO2H CH3OC6H4COCH3

33.05 36.07 33.03 149.21 90.08 150.18

1 , 1186 13, 1187 13, 1187 42, 938 3, 232 8, 85

0.8127 0.888 0.815 1.340 1.174 1.09020 4

1.3270 1.325620 1.329020 1.415820 1.539320

202–204 13118mm

⬎110 108

CH3OC6H4COCH3

150.18

8, 86

1.094

1.541020

239–241

⬎110

s aq

CH3OC6H4COCH3

150.18

8, 87

1.08241 4

1.5335

36–38

15426mm

⬎110

v s alc, eth

CH3OCH"CHCN CH3OC6H4NH2 CH3OC6H4NH2 CH3OC6H4NH2

83.09 123.16 123.16 123.16

13, 358 13, 404 13, 435

0.990 1.09815 15 1.096 1.087

1.455020 1.573020 1.579420

5–6 ⫺10 57–60

225 251 240–243

Metanilic acid, a116 Methacholine chloride, a49 Methacrolein, m27 Methacrolein diacetate, m32 Methallyl alcohol, m400 Methallyl chloride, c182

Mesidine, t335 Mesitol, t387 Mesitylene, t359 Mesityl oxide, m370 Mesoxylurea, a73 Mesyl chloride, m36

⫺97.8 281 dec

76 98 ⬎110

3 aq; i eth; v sl s alc misc aq, alc, eth

DEAN 37261 (McGHP)

m37

i aq; misc alc, eth s alc, acid; sl s aq v s alc; sl s aq

Methanal, f31 Methanoic acid, f36 Methenamine, h49 Malononitrile dimer, a267 Methone, d596 Methoxyacetaldehyde dimethyl acetal, t340

RIGHT ROTATED

m15

m17

m19

m26

INTERACTIVE

No. m51 m52 m53 m54 m55 m56 m57 m58

1.256

m59 m60 m61

m67 m68 m69

Beilstein reference

Density, g/mL

Refractive index

CH3OC6H4CHO

136.15

8, 43

1.127

1.56020

CH3OC6H4CHO

136.15

8, 59

1.119

1.553320

CH3OC6H4CHO

136.15

8, 67

1.119

1.571320

CH3OC6H4CONH2 CH3OC6H5 CH3OC6H4SO2Cl

151.17 108.14 206.65

102, 100 6, 138 11, 243

0.994220

1.517020

CH3OC6H4CO2H

152.15

10, 64

1.180

CH3OC6H4CO2H

152.15

10, 137

CH3OC6H4CO2H

152.15

10, 154

CH3OC6H4COCl

170.60

10, 163

CH3OC6H4CH2OH

138.17

6, 897

CH3OC6H4CH2NH2 CH3OC6H4C6H5 CH3OCH(CH3)CH2CH2OH CH3OCH"CHCOCH3

137.18 184.24 104.15 100.12

13, 606 6, 672

CH3OC6H4CH"CHCHO

162.19

(CH3)2C(OCH3)(CH2)3CH(CH3)CH2CHO

110.16

63, 367

198.22

173, 1590

186.30 104.11

194, 617

Melting point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

238

117

14350mm

⬎110

⫺1

248

108

misc alc

164–167 ⫺37.5 40–43

295 153.8

108 51 ⬎110

s aq; v s alc; sl s eth 1 aq; misc alc, eth dec aq; s alc, eth

100

200

0.5 aq; v s alc, eth

104

17210mm

s hot aq, alc, eth

185

275–280

0.04 aq; v s alc, chl

1.581020

22

14514mm

87

1.10925 4

1.544220

23–25

259

⬎110

1.05015 1.023 0.922920 20 0.982

1.546220 1.610520 1.414520 1.468020

30–33 ⫺85

236–237 274 161.1 200

⬎110 ⬎110 46 63

44–48

1300.6mm

⬎110

148–150

36

1.3854

0.940

37–39

Boiling point,⬚C

1.481920

⬎110

42–45 0.877

1.437420

600.45mm

98

1.092

1.409120

129–130

31

sl s alc, bz; i eth

i aq (dec); s alc (dec); s acet, bz i aq; s alc, eth v s aq, alc, eth misc aq

INTERACTIVE

m70

Formula weight

ROTATED

m66

2-Methoxybenzaldehyde 3-Methoxybenzaldehyde 4-Methoxybenzaldehyde 4-Methoxybenzamide Methoxybenzene 4-Methoxybenzenesulfonyl chloride 2-Methoxybenzoic acid 3-Methoxybenzoic acid 4-Methoxybenzoic acid 4-Methoxybenzoyl chloride 4-Methoxybenzyl alcohol 4-Methoxybenzylamine 2-Methoxybiphenyl 3-Methoxy-1-butanol 4-Methoxy-3-buten-2one 2-Methoxycinnamaldehyde 1-Methoxy-1,4-cyclohexadiene 2-Methoxydibenzofuran 7-Methoxy-3,7dimethyloctanal 2-Methoxy-1,3dioxolane

Formula

LEFT

m62 m63 m64 m65

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m73 m74 m75 m76 m77 m78 m79 m80 m81

1.257

m82 m83 m84 m85 m86

1-Methoxynaphthalene

0.964620 1.180

1.402120 1.438020

⫺85.1

124 245–250

39 ⬎110

misc aq

120.15

1.03520 4

1.426420

⫺50

194

96

misc aq, alc, bz, eth, ketones

CH3OCH2CH2OCH2Cl

124.57

1.091

1.427020

5013mm

⬎110

CH3CO2CH2CH2OCH3 CH3COCH2CO2CH2CH2OCH3

118.13 160.17

2, 141

1.004920 1.090

1.400220 1.433920

144 12020mm

49 103

misc aq

CH3OCH2CH2NH2 CH3OCH2CH2O2CCH2CN

75.11 143.14

42, 718 24, 1891

0.864 1.127

1.405420 1.434020

95 1001mm

9 ⬎110

v s aq, alc

164.20 137.18

6, 970 132, 388

1.128

1.548220

CH3OC6H3(CH3)NH2

52–54

14611mm 235

⬎110 ⬎110

s aq; v s alc, bz, eth

CH3OC6H3(CH3)NH2

137.18

132, 330

1.065

1.564720

13–14

248–249

⬎110

s alc

CH3OC(CH3)2CH2CH2OH

118.18

13, 2198

0.926

1.428020

173–175

71

NCCH2CO2CH(CH3)CH2OCH3

157.17

1.030

1.431020

1052mm

62

CH3OC6H3(CH3)OH

138.17

6, 878

1.092

1.537220

222

99

CH3OC6H3(CH3)(NO2)NH2

182.18

133, 1575

(CH3)2C 9 CH(OCH3)

102.13

173, 1035

0.904

1.392920

94

6

O C10H7OCH3

158.20

6, 606

1.090

1.622020

13512mm

⬎110

CH3OCH2CH2OH CH3OCH2CH2OCH2CO2H

76.10 134.13

CH3OCH2CH2OCH2CH2OH

Methoxyethane, e210

1, 467 33, 374

⫺70

5 168–170

RIGHT

m87

2-Methoxyethanol 2-(2-Methoxyethoxy)acetic acid 2-(2-Methoxyethoxy)ethanol 2-Methoxyethoxymethyl chloride 2-Methoxyethyl acetate 2-Methoxyethyl acetoacetate 2-Methoxyethylamine 2-Methoxyethyl cyanoacetate 1-Methoxy-2-indanol 2-Methoxy-5-methylaniline 4-Methoxy-2-methylaniline 3-Methoxy-3-methyl1-butanol 2-Methoxy-1-methylethyl cyanoacetate 2-Methoxy-4-methylphenol 5-Methoxy-2-methyl4-nitroaniline 1-Methoxy-2-methylpropylene oxide

DEAN 37261 (McGHP)

m71 m72

2-Methoxyethoxychloromethane, m74

ROTATED

m67

m68

m70

m79

INTERACTIVE

No. m88 m89 m90 m91 m92 m93 m94

1.258

m95 m96

m102 m103 m104

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

C10H7OCH3 CH3OC6H3(NO2)NH2

158.20 168.15

6, 640 13, 390

73–75 140–142

CH3OC6H3(NO2)NH2

168.15

13, 389

117–119

s alc, hot bz, HOAc

CH3OC6H3(NO2)NH2

168.15

13, 521

123–126

sl s aq; s alc, eth

CH3OC6H4NO2

153.14

6, 217

CH3OC6H3(NO2)CO2H

197.15

10, 181

192–194

CH3O(C5H3N)NO2

154.13

213, 33

108–109

CH3OC6H3(NO2)CH3

167.16

6, 411

1.207

1.552520

CH3OC6H3CH2CH2NH2

151.21

13, 626

1.033

1.537920

CH3OC6H4OH CH3OC6H4OH CH3OC6H4OH CH3OC6H4OCH2CH(OH)CH2OH

124.14 124.14 124.14 198.22

6, 768 6, 813 6, 843 63, 4411

1.112(lg) 1.131

1.5429 1.551020

CH3OC6H4CH2CO2H

166.18

10, 190

CH3OC6H4CH2OCH3

164.20

83, 397

CH3OC6H4CH2CN

147.18

10, 188

CH3OC6H4CH2CN

147.18

10, 191

1.085

1.530020

90.12 72.11

12, 536 1, 435

0.91920 20 0.735

1.402121 1.382020

CH3OCH2CH(OH)CH3 CH3C(OCH3)"CH2

1.252720 4

1.054

1.516120

274

Solubility in 100 parts solvent s bz, eth, CS2

277

⬎110

267

⬎110

14020mm

⬎110

28 ⬍ ⫺17.5 55–57 76–80

205 1155mm 243

82 ⬎110 ⬎110

86–88

1403mm

10.5

17

1.525020

13010mm 65–68

⫺97

0.17 aq; s alc, eth

1.5 aq; misc alc, eth misc alc, eth; sl s aq v s bz; s alk

1 aq; v s alc; s eth ⬎110

14315mm

s alc, eth s hot bz

286–287

⬎110

120.1 34–36

33 ⫺29

misc aq, acet, bz, eth

INTERACTIVE

m105 m106

Formula weight

ROTATED

m101

2-Methoxynaphthalene 2-Methoxy-4-nitroaniline 2-Methoxy-5-nitroaniline 4-Methoxy-2-nitroaniline 2-Methoxynitrobenzene 4-Methoxy-3-nitrobenzoic acid 2-Methoxy-5-nitropyridine 4-Methoxy-2-nitrotoluene 4-Methoxyphenethylamine 2-Methoxyphenol 3-Methoxyphenol 4-Methoxyphenol 3-(4-Methoxyphenoxy)-1,2propanediol 4-Methoxyphenylacetic acid 2-Methoxyphenylacetone 2-(Methoxyphenyl)acetonitrile 4-(Methoxyphenyl)acetonitrile 1-Methoxy-2-propanol 2-Methoxypropene

Formula

LEFT

m97 m98 m99 m100

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m108 m109 m110 m111 m112 m113 m114

1.259

m115 m116 m117 m118 m119 m120 m121 m122 m123 m124

trans-1-Methoxy-4(1-propenyl)benzene 2-Methoxy-4-propenylphenol 2-Methoxy-4-(2propenyl)phenol 3-Methoxypropionitrile 4-Methoxypropiophenone 3-Methoxypropylamine 2-Methoxypyridine 6-Methoxy-1,2,3,4tetrahydronaphthalene 6-Methoxy-1-tetralone 2-Methoxytoluene 3-Methoxytoluene 4-Methoxytoluene Methoxytrimethylsilane N-Methylacetamide 4⬘-Methylacetanilide Methyl acetate

CH3OC6H4CH"CHCH3

148.21

6, 566

0.988320 4

1.561520

21.4

237

90

CH3OC6H3(OH)CH"CHCH3

164.20

6, 955

1.08720 4

1.574820

⫺10

266

⬎112

Methyl acetoacetate 4⬘-Methylacetophenone

misc chl, eth; 50 alc; s bz, EtOAc misc alc, eth; sl s aq

CH3OC6H3(OH)CH2CH"CH2

164.20

6, 961

1.0664

1.5408

⫺9.2

255

⬎112

CH3OCH2CH2CN CH3OC6H4COCH2CH3

85.11 164.20

31, 113 8, 103

0.937 1.071

1.403020 1.546520

27–29

165 274

61 61

CH3O(CH2)3NH2 CH3O(C5H4N)

89.14 109.13 162.23

43, 739 21, 44 62, 537

0.874 1.038 1.033

1.417520 1.502929 1.540220

118733mm 142 901mm

22 32 ⬎110

CH3OC6H4CH3 CH3OC6H4CH3 CH3OC6H4CH3 CH3OSi(CH3)3

176.22 122.17 122.17 122.17 104.23

92, 889 6, 352 6, 376 6, 392 43, 1856

0.985115 15 0.969725 25 0.96925 25 0.756020 4

1.516120 1.513120 1.511220 1.367820

17111mm 170–172 175–176 174 57–58

51 54 53 ⫺30

i aq; v s alc, eth s alc, bz, eth; i aq s alc, eth; i aq

CH3CONHCH3 CH3OCONHC6H4CH3 CH3CO2CH3

73.10 149.19 74.08

4, 58 12, 920 2, 224

0.946035

1.425335

108

s aq

0.934220 4

24 aq; misc alc, eth

CH3COCH2CO2CH3 CH3C6H4COCH3

116.12 134.18

3, 632 7, 307

1.075720 1.0051

⫺10 (CC) 77 92

20

77–79

1.361920

30.6 150 ⫺98

206 307 57

1.418620 1.532820

27.5 22–24

171.7 226

3-Methoxypropionaldehyde dimethyl acetal, t341

6-Methoxytetralin, m114

misc alc, chl, eth; s HOAc, alk; i aq

misc aq

50 aq; misc alc i aq; v s alc, eth

RIGHT

␣-Methoxy-␣-phenylacetophenone, b49

20 4

DEAN 37261 (McGHP)

m107

ROTATED

m114

m115

INTERACTIVE

Methyl 4-acetoxybenzoate Methyl acrylate Methylamine 1-(Methylamino)anthraquinone Methyl 2-aminobenzoate Methyl 3-aminocrotonate 2-(Methylamino)ethanol 4-Methylaminophenol sulfate Methyl 2-(aminosulfonyl)benzoate N-Methylaniline N-Methylanilinium trifluoroacetate 2-Methylanthraquinone Methylarsonic acid 4-Methylbenzaldehyde Methyl benzenesulfonate 2-Methylbenzimidazole Methyl benzoate 2-Methylbenzoic acid 3-Methylbenzoic acid 4-Methylbenzoic acid 4-Methylbenzophenone 2-Methylbenzothiazole

m126 m127 m128 m129 m130 m131 m132

1.260

m133 m134 m135 m136 m137 m138 m139 m140 m141 m142 m143 m144 m145 m146

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

CH3CO2C6H4CO2CH3

194.19

10, 159

H2C"CHCO2CH3 CH3NH2

86.09 31.06 237.26

2, 399 4, 32 14, 179

0.954120 4 0.6994⫺11

1.404020

⫺76.5 ⫺93.5 170–172

80.2 ⫺6.3

⫺3 (CC) 0

6 aq; s alc, eth 959 mL aq; 10.5 bz

H2NC6H4CO2CH3

151.17

14, 317

1.16819 4

1.582020

24

256

104

sl s aq; v s alc, eth

CH3C(NH2)"CHCO2CH3

115.13

3, 632

75.11

4, 276

159

72

misc aq, alc, eth

(CH3NC6H4OH)2 · H2SO4

344.39

13, 441

260 dec

H2HSO2C6H4CO2CH3

215.23

11, 377

126–128

C6H5NHCH3 C6H5NHCH3 · HO2CCF3

107.16 221.18

12, 135

222.24

7, 809

139.96 120.15 172.20

4, 613 7, 297 112, 20

132.17

23, 145

CH3NHCH2CH2OH

CH3AsO(OH)2 CH3C6H4CHO C6H5SO2OCH3

C6H5CO2CH3 CH3C6H4CO2H CH3C6H4CO2H CH3C6H4CO2H CH3C6H4COC6H5

82–84

81–83 0.93720

0.98920 4

1.438720

1.568420

⫺57 65–66

4 aq; sl s alc; i eth

196

78

170–173

v s bz; s alc, eth

161 1.019417 4 1.288904

1.544720 1.515120

15 4

15

⫺4

sl s aq; s alc, eth

205 15420mm

80

176–177

v s aq; s alc misc alc, eth; sl s aq v s alc, chl, eth s alk, hot aq; sl s alc

136.15 136.15 136.15 136.15 196.25

9, 109 9, 462 9, 475 9, 483 7, 440

1.0933 1.062 1.054

1.5205

⫺15 103.7 111–113 180 57

199.5 258–259 263 274–275 326

83

0.2 aq; misc alc, eth sl s aq; v s alc 0.09 aq; v s alc v s alc, eth v s bz, eth

149.22

27, 46

1.173

1.617020

12–14

238

102

s alc, HOAc; i aq

INTERACTIVE

m125

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m149 m150 m151 m152 m153 m154 m155 m156 m157

1.261

2-Methylbenzoxazole ␣-Methylbenzyl acetate ␣-Methylbenzyl alcohol 2-Methylbenzyl alcohol (⫾)-␣-Methylbenzylamine 4-Methylbenzylamine Methylbis(trimethylsilyloxy)vinyl ether Methyl bromoacetate (⫾)-Methyl 2-bromobutyrate Methyl 2-bromopropionate 2-Methyl-1,3butadiene

133.15 164.20

27, 46 6, 476

1.121 1.028

1.549720 1.494520

8–10

CH3CO2CH(CH3)C6H5

178 9512mm

75 91

C6H5CH(CH3)OH

122.17

6, 475

1.019113 4

1.526520

20

204745mm

85

v s alc; s bz, chl

CH3C6H4CH2OH

122.17

6, 484

1.540820

33–36

11014mm

104

5 aq; 5 alc; s eth

C6H5CH(CH3)NH2

121.18

12, 1094

0.940

1.526020

185

79

4.2 aq; misc alc, eth

CH3C6H4CH2NH2 CH3Si[OSi(CH3)2]CH"CH2

121.18 148.55

12, 1141 44, 4184

0.952 0.864

1.534020 1.397020

195 488.8mm

75 51

BrCH2CO2CH3 CH3CH2CH(Br)CO2CH3

152.98 181.04

2, 213 2, 282

1.616 1.573

1.458620 1.45220

5215mm 13850mm

62 68

s alc

CH3CH(Br)CO2CH3

167.01

2, 253

1.497

1.542020

5119mm

51

s alc

68.12

1, 252

0.68120 4

1.421620

34.1

⫺53

misc alc, eth

H2C"C(CH3)CH"CH2

5-Methyl-o-anisidine, m81 Methylanisoles, m116 thru m118 Methyl anthranilate, m129 Methylanthranilic acid, a207, a208 Methylbenzene, t166 4-Methylbenzenesulfonic acid, t176 Methyl benzilate, m239 2-Methylbenzonitrile, t184

⫺146.0

4-Methylbenzonitrile, t185 o-Methylbenzyl alcohol, p109 N-Methylbenzylamine, b108 Methylbenzyl bromide, b343, b344 Methylbenzyl chlorides, c269 thru c271 Methylbis(2-chloroethoxy)silane, b162 N-Methylbis(2-chloroethyl)amine, b164 Methyl bromide, b225

RIGHT

Methylal, d507 Methyl alcohol, m38 Methylallene, b448 Methylaminoacetaldehyde dimethyl acetal, d508 ␣-(1-Methylaminoethyl)benzyl alcohol, e2 Methylanilines, t180 thru t182 Methyl o-anisate, m304 Methyl p-anisate, m305 2-Methyl-p-anisidine, m80

12–13

DEAN 37261 (McGHP)

m147 m148

ROTATED

m128

m136

m140

m146

m147

INTERACTIVE

1.262

m158 m159 m160 m161 m162

2-Methylbutane 2-Methyl-1-butenethiol 2-Methyl-2-butanethiol 2-Methyl-1-butanol 2-Methyl-2-butanol

CH3CH2CH(CH3)2 CH3CH2CH(CH3)CH2SH CH3CH2C(CH3)2SH CH3CH2CH(CH3)CH2OH CH3CH2C(CH3)2OH

m163

3-Methyl-1-butanol

(CH3)2CHCH2CH2OH

m164 m165 m165a m166 m167 m168

3-Methyl-2-butanol 3-Methyl-2-butanone 2-Methyl-1-butene 2-Methyl-2-butene 3-Methyl-1-butene cis-2-Methyl-2butenoic acid trans-2-Methyl-2butenoic acid 3-Methyl-2-butenoic acid 2-Methyl-3-buten-2-ol 3-Methyl-2-buten-1-ol 3-Methyl-3-buten-1-ol 2-Methyl-1-buten-3yne N-Methylbutylamine 1-Methylbutylamine 3-Methylbutyl 3methylbutyrate 3-Methyl-1-butyne 2-Methyl-3-butyne-2-ol 2-Methylbutyraldehyde 3-Methylbutyraldehyde Methyl butyrate 2-Methylbutyric acid

m169 m170

m175 m176 m177 m178 m179 m180 m181 m182 m183

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

72.15 104.22 104.22 88.15 88.15

1, 134 12, 421 11, 196 1, 388 1, 388

0.619720 0.848 0.842 0.81620 4 0.809620

1.353720 1.446520 1.438520 1.410020 1.405020

⫺159.9

88.15

1, 392

0.812915 4

(CH3)2CHCH(OH)CH3 (CH3)2CHCOCH3 C2H5C(CH3)"CH2 CH3CH"C(CH3)2 (CH3)2CHCH"CH2 CH3CH"C(CH3)CO2H

88.15 86.13 70.14 70.14 70.14 100.12

1, 391 1, 682 1, 211 1, 211 1, 213 2, 428

CH3CH"C(CH3)CO2H

100.12

(CH3)2C"CHCO2H

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

⫺103.9 ⬍⫺70 ⫺9.0

27.8 117 99.1 128 102.0

⫺56 19 ⫺1 43 21

1.408515

⫺117

131

45

0.817920 0.80220 4 0.650 0.662020 4 0.627220 4 0.98347 4

1.409120 1.388020 1.378020 1.387820 1.363820 1.443747

⫺92 ⫺137.6 ⫺133.8 ⫺168 45

112.9 94.3 31 38.6 20 185

38 6 ⬍ ⫺34 ⫺45 ⫺56

2, 430

0.969

1.434281

64

198

s alc, eth; v s hot aq

100.12

2, 432

1.00624

69

194–195

s aq, alc, eth

(CH3)2C(OH)CH"CH2 (CH3)2C"CHCH2OH H2C"C(CH3)CH2CH2OH H2C"C(CH3)C#CH

86.13 86.13 86.13 66.10

1, 444 1, 444

1.417020 1.444020 1.433720 1.414020

2.6

98–99 140

11, 126

0.824 0.848 0.853 0.695

⫺113

32

13 43 36 ⫺6

CH3CH2CH2CH2NCH3 CH3CH2CH2CH(CH3)NH2 (CH3)2CHCH2CH2O2CCH2CH(CH3)2 (CH3)2CHC#CH (CH3)2C(OH)C#CH CH3CH2CH(CH3)CHO (CH3)2CHCH2CHO CH3CH2CH2CO2CH3 CH3CH2CH(CH3)CO2H

87.17 87.17 172.27

4, 157 4, 177 2, 312

0.736 0.738420 4 0.854125

1.399520 1.402920 1.410025

⫺75

91 91 190.4

1 35 84

68.12 84.12 86.13 86.13 102.13 102.13

1, 251 11, 235 11, 352 1, 684 2, 270 2, 305

0.66620 4 0.867220 20 0.804 20 0.78520 0.89820 4 1.405520

1.374020 1.420920 1.391920 1.388220 1.386020

⫺89.8 2.6

26.4 104 90–92 92–93 103 176.5

25 4 19 11 73

⫺51 ⫺85.8

0.005 aq; misc alc s alc, eth; i aq s alc, eth; i aq 3 aq; misc alc, eth 11 aq; misc alc, bz, chl, eth 2 aq; misc alc, bz, chl, eth, PE, HOAc 2.8 aq; misc alc, eth misc alc, eth misc alc, eth; i aq misc alc, eth s alc, eth; v s hot aq

LEFT

m171 m172 m173 m174

Formula

misc aq, alc, eth misc alc, eth misc alc, eth misc aq, acet, bz misc alc, eth; sl s aq 1.4 aq; misc alc, eth

INTERACTIVE

Name

ROTATED

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m187 m188 m189 m190 m191 m192 m193 m194 m195

1.263

m196 m197 m198 m199

3-Methylbutyric acid 3-Methylbutyronitrile 3-Methylbutyryl chloride Methyl carbamate Methyl chloroacetate Methyl 2-chloroacetoacetate Methyl 4-chloroacetoacetate Methyl 3-chlorobenzoate Methyl-4-chlorobenzoate Methyl 4-chlorobutyrate Methyl chloroformate Methyl 3-(chloroformyl)propionate Methyl 2-chloropropionate 2-Methylcinnamaldehyde Methyl transcinnamate 6-Methylcoumarin

(CH3)2CHCH2CO2H (CH3)2CHCH2CN (CH3)2CHCH2COCl

102.13 83.13 120.58

0.930820 4 0.792519 4 0.98520 4

2, 309 22, 278 2, 315

56 4 20 20

1.403320 1.392720 1.416120

H2NCO2CH3 ClCH2CO2CH3 CH3COCH(Cl)CO2CH3

75.07 108.52 150.56

3, 21 2, 197

1.136 1.238 1.236

1.422020 1.446520

ClCH2COCH2CO2CH3

150.56

32, 426

1.305

1.456420

ClC6H4CO2CH3

170.60

9, 338

1.227

1.492320

ClC6H4CO2CH3

170.60

9, 340

1.38220

ClCH2CH2CH2CO2CH3

136.58

2, 278

1.126814

1.432120

ClCO2CH3 CH3O2CCH2CH2COCl

94.50 150.56

3, 9 22, 553

1.22320 4 1.223

CH3CH(Cl)CO2CH3

122.55

2, 248

C6H5CH"C(CH3)CHO

146.19

7, 369

C6H5CH"CHCO2CH3

162.19

9, 581

160.17

17, 337

18

177 130 137

51 71

854mm

102

10112mm

104

42–44

4 aq; s alc, chl, eth misc alc, eth dec aq, alc; s eth 220 aq; 73 alc; s eth i aq; misc alc, eth

106

s alc

175–176

59

v s eth; s alc, acet

1.386520 1.440220

70–72 653mm

17 73

misc alc, bz, chl, eth

1.075

1.419320

132–133

38

s alc

1.040717 4

1.604520

14927mm

79

36–38

262

⬎110

75–76

303725mm

Methyl carbitol, m73 4-Methylcatechol, d438 Methyl cellosolve, m71 Methyl cellosolve acetate, m75 Methyl chlorocarbonate, m194 Methyl chloroform, t231

INTERACTIVE

m199

21

70

ROTATED

2-Methylbutyl isovalerate, m177 Methyl tert-butyl ketone, h70 Methyl caprate, m226 Methyl caproate, m270 Methyl caprylate, m349 Methyl carbazate, m275

56–58 ⫺32 ⫺32.7

176.5 129 115–117

RIGHT

3-Methyl-1-butencarboxylic acid, m369 cis-2-Methyl-2-butenedioic acid, c284 Methyl 2-buten-1-oate, m200 3-Methylbutyl acetate, i91 2-Methylbutylamine, a246 Methyl tert-butyl ether, b572

⫺29.3 ⫺101

DEAN 37261 (McGHP)

m184 m185 m186

Methyl crotonate Methyl cyanoacetate Methylcyclohexane Methyl cyclohexanecarboxylate 4-Methyl-1,2-cyclohexanedicarboxylic anhydride 1-Methylcyclohexanol cis-2-Methylcyclohexanol trans-2-Methylcyclohexanol cis-3-Methylcyclohexanol trans-3-Methylcyclohexanol cis-4-Methylcyclohexanol trans-4-Methylcyclohexanol 2-Methylcyclohexanone 3-Methylcyclohexanone 4-Methylcyclohexanone 1-Methyl-1-cyclohexene 4-Methyl-1-cyclohexene 6-Methyl-3-cyclohexene-1-methanol

m204

m205 m206 m207

1.264

m208 m209 m210 m211 m212 m213 m214 m215 m216 m217

CH3CH"CHCO2CH3 NCCH2CO2CH3 C6H11CH3 C6H11CO2CH3

Formula weight 100.12 99.09 98.19 142.20

Beilstein reference 2, 410 2, 584 5, 29 9, 8

168.19

Density, g/mL

Refractive index

0.944420 4 1.122525 0.769420 0.995416 4

1.424220 1.416625 1.422120 1.443020

1.162

1.477420

Melting point,⬚C

⫺22.5 ⫺126.6

Boiling point,⬚C 121 201 100.9 183

Flash point,⬚C 4 ⬎110 ⫺4 60

Solubility in 100 parts solvent v s alc, eth; i aq misc alc, eth i aq; s alc, eth

⬎110

CH3C6H10OH CH3C6H10OH

114.19 114.19

6, 11 62, 17

0.925125 0.936020 4

1.458725 1.464030

25 7

155 165

67 58

i aq; b bz, chl misc alc, eth

CH3C6H10OH

114.19

6, 11

0.924720 4

1.461620

⫺2

167.5

65

misc alc; s eth

CH3C6H10OH

114.19

6, 12

0.915520

1.457220

⫺6

168

62

misc alc, eth

CH3C6H10OH

114.19

6, 12

0.921420

1.458020

⫺0.5

167

62

CH3C6H10OH

114.19

6, 14

0.917020

1.461420

⫺9.2

173

70

misc alc, eth

CH3C6H10OH

114.19

6, 14

0.911821 4

1.455920

174

70

misc alc; s eth

CH3C6H9("O)

112.17

7, 14

0.92520 4

1.447820

162

46 (CC)

i aq; s alc, eth

CH3C6H9("O)

112.17

7, 15

0.915520 4

1.446020

169

51

i aq; s alc, eth

CH3C6H9("O)

112.17

7, 18

0.91620 4

1.445520

171

40

i aq; s alc, eth

96.17

5, 66

0.80920 4

1.450220

⫺121

111

⫺3

i aq; s alc, eth

96.17

5, 67

0.799

1.441220

⫺115.5

102

⫺1

i aq; s alc, eth

0.954

1.483020

126.20

INTERACTIVE

m200 m201 m202 m203

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m219 m220 m221 m222 m223 m224 m225 m226 m227 m228

1.265

m229 m230 m231 m232

C6H11NHCH3

113.20

12, 6

0.868

1.456020

149

29

CH3C6H10NH2

113.20

12, 10

0.855

1.452520

150730mm

22

20

151–154

26

CH3C6H10NH2

113.20

12, 12

0.955

1.4531

160.26

54, 1435

0.941

1.497620

⫺51

200

26

84.16 112.13

5, 27 71, 310

0.748720

1.409720

⫺142.4 105–107

71.8

⫺23

0.013 aq

98.15

72, 13

0.920020 4

1.434720

⫺76

139

26

s aq; v s alc, eth

C3H5CO2CH3

100.12

91, 3

0.985

1.418120

119

17

CH3(CH2)8CO2CH3 Cl2CHCO2CH3

186.30 142.97 183.03

2, 356 2, 203

0.873 1.380819 1.245

1.425520 1.442120 1.463920

223 143 748mm

94 80 74

i aq; misc alc, eth i aq; s alc

ClCH2CH(Cl)CO2CH3

157.00

21, 111

1.328220 4

1.444720

9250mm

42

s alc

CH3N(CH2CH2OH)2

119.16

4, 284

1.037720

1.468520

248

126

misc aq, alc

(CH3O)2C6H3CO2CH3

196.20

10, 396

59–62

283

(CH3O)2C6H3CO2CH3

196.20

10, 405

43

298

C5H9CH3

trans-2-Methylcrotonic acid, m169

Methyl cyanide, a29

⫺18 ⫺52

⬎110

Methyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate, m292

ROTATED

CH2OH H3C

m204

m215

m216

m217

RIGHT

N-Methylcyclohexylamine 3-Methylcyclohexylamine 4-Methylcyclohexylamine Methylcyclopentadiene dimer Methylcyclopentane 3-Methyl-1,2-cyclopentanedione 2-Methylcyclopentanone Methyl cyclopropanecarboxylate Methyl decanoate Methyl dichloroacetate Methyl 2,2-dichloro-1methylcyclopropanecarboxylate Methyl 2,3-dichloropropionate N-Methyldiethanolamine Methyl 3,4-dimethoxybenzoate Methyl 3,5-dimethoxybenzoate

DEAN 37261 (McGHP)

m218

m221

m223

m224

m225

m228

INTERACTIVE

Methyl 3-(dimethylamino)propionate Methyl 2,5-dimethyl3-furoate Methyl 2,2-dimethylpropionate N-Methyldioctylamine 4-Methyl-1,3-dioxane N-Methyldiphenylamine Methyl diphenylglycolate 3-Methyl-1,1-diphenylurea Methyleneaminoacetonitrile N,N⬘-Methylenebisacrylamide 2,2⬘-Methylenebis(4-chlorophenol) 4,4⬘-Methylenebis(2,6-di-tert-butylphenol 4,4⬘-Methylenebis(N,N-dimethylaniline) 1,1⬘-Methylenebis(3methylpiperidine) 4,4⬘-Methylenebis(phenylisocyanate) Methylene blue 4,4⬘-Methylenedianiline

m234 m235 m236 m237 m238 m239

1.266

m240 m241 m242 m243 m244

m245

m246 m247 m248 m249

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

131.18

4, 403

0.917

1.418420

154

51

154.17

18, 398

1.037

1.475020

198

80

(CH3)3CCO2CH3

116.16

21, 139

0.873

1.388020

101–103

⫺1

(C8H17)2NCH3

43, 381 194, 49 12, 180

1.066 0.976 1.04820 4

1.442420 1.415020 1.619320

⫺30.1 ⫺45 ⫺7.6

16515mm 114 1356mm

⬎110 22

(C6H5)2NCH3

255.49 102.13 183.26

(C6H5)2C(OH)CO2CH3

242.27

10, 344

74–76

18713mm

(C6H5)2NCONHCH3

226.28

12,2, 852

172–174

Merck: 11, 5976

129

(CH3)2NCH2CH2CO2CH3

CH2 "NCH2CN

68.08

Solubility in 100 parts solvent

misc alc, eth; sl s aq

i aq; s alc, eth

s hot aq, alc; sl s bz

⬎300

H2C"CHC("O)NHCH2NHC("O)CH"CH2 CH2[C6H3(Cl)OH]2

154.17 269.13

6,3, 5408

168–172

CH2{C6H2[C(CH3)3]2OH}2

424.67

64, 6811

156–158

CH2[C6H4N(CH3)2]2

254.38

13, 239

88–89

CH2[CH3C5H9N]2

210.37

CH2(C6H4NCO)2

250.26

13,3, 461

CH2(C6H4NH2)2

373.90 198.26

27, 393 13, 238

0.887 1.180

100 EtOH; 100 eth; s PE 28940mm

16050mm

⬎110

42–44

2005mm

⬎110

190 dec 89–91

399

221

1.473420

4 aq; 1.3 alc; s chl v s alc, bz, eth; sl s aq

INTERACTIVE

m233

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m251 m252

m253

3,4-Methylenedioxybenzaldehyde 1,2-Methylenedioxybenzene 3,4-Methylenedioxy-6propylbenzyldiethyleneglycol butyl ether Methylenesuccinic acid

H2C"C(CO2H)CH2CO2H

150.13

19, 115

37

122.12

19, 20

338.45

3

19 , 779

1.059

130.10

2, 760

1.573

1.064

1.5398

⬎110

173

55

1mm

1.498

180

171

167

4,4⬘-Methylenedianiline, d46 Methylene dimethyl ether, d507 1,1⬘-Methylenedipiperidine, d776 Methylene fluoride, d409

Methyldinitrophenol, d715, d716 Methyl enanthate, m266 Methylene bromide, d110 Methylene bromochloride, b305 Methylene chloride, d235

264

0.2 aq; v s alc, eth

misc alc, bz, geons

8.2 aq; 20 alc; v sl s bz, chl, eth, PE

DEAN 37261 (McGHP)

m250

Methylene iodide, d452 ␤-Methylene-␤-propiolactone, d483 (1-Methylethyl)benzene, i103 Methyl ethyl ketone, b475

1.267 m237

m248

RIGHT

m234

ROTATED

m250

m251

m252

INTERACTIVE

No. m254 m255 m256 m257 m258 m259 m259a m260 m261

1.268

m262 m263

Beilstein reference

Density, g/mL

Refractive index

74.13

41, 415

0.841

1.439520

59.07 135.17 60.05 110.11 82.10 126.11 327.35

4, 58 12, 234 2, 18 17, 289 17, 36 18, 274

0.998825 1.095 0.981515 1.107218 4 0.91520 4 1.17920 2.633720 4

1.430025 1.561020 1.346515 1.526320 1.433220 1.487920 1.577020

195.22 194.18

Merck: 12, 6154 31, 179

1.4630 4

NCCH2CH2CH(CH3)CN

108.14

2, 656

0.950

1.434020

CH3NHCH2CO2H HOCH2CO2CH3 CH3(CH2)5CO2CH3 (CH3)2CH(CH2)3CH(OH)CH3 C2H5CH(CH3)CH2COC2H5 (CH3)2C"CHCH2CH2COCH3

89.09 90.08 144.22 130.23 128.22 126.20

4, 345 3, 236 2, 339 1, 421 11, 363 13, 3010

1.16818 4 0.881520 4 0.803 0.823 0.85516 4

1.417020 1.411520 1.424020 1.414220 1.439220

CH3(CH2)14CO2CH3 CH3(CH2)4CO2CH3 (CH3)2CHCH2CH2COCH3 CH3(CH2)4CH(NH2)CH3

2, 372 2, 323 12, 756 4, 194 24, 244 42, 957 31, 46

0.852 0.903804 0.88820 4 0.766518

1.451220 1.403823 1.406220 1.417520

CH3NHNH2 H2NNHCO2CH3

270.46 130.19 114.19 115.22 114.10 46.07 90.08

0.866

1.422520

HO2CCH2CH2CH2CO2CH3

146.14

22, 565

1.169

1.438120

CH3NHCH2CH2NH2 HC("O)NHCH3 C6H5N(CH3)CHO HCO2CH3

CH3GeBr3

Melting point,⬚C

⫺4 8–13 ⫺99 ⫺88

Boiling point,⬚C

Flash point,⬚C

114–116

42

199.5 244 31.7 187 63–66 181 168

98 126 ⫺19 72 ⫺22 73

168

2000.2mm

⫺45

269–271

126

151 173.5 172 157–162 7318mm

67 52 67 43 50

19615mm 151 144 144 subl 87.5 10812mm

⬎110 45 3641 54

⫺67 32–34 ⫺71 ⫺73.9 157 ⫺52.4 70–73

misc aq 30 aq; misc alc s aq; v s alc; misc eth 0.3 aq s alc, eth; sl s aq

100 aq25; 1.2 alc70

128–129

208 dec 74 ⫺55.8

Solubility in 100 parts solvent

15110mm

63 aq; 1.6 alc; i eth

21

⬎110

42 aq; sl s alc s aq; misc alc, eth s alc, eth; sl s aq

misc alc, eth s alc, chl, eth v s alc, eth 0.5 aq; misc alc, eth sl s aq; s alc, eth s aq, alc; 3 eth misc aq, alc; s PE

INTERACTIVE

m276

Methyl-␣-D-glucopyranoside (⫾)-2-Methylglutaronitrile N-Methylglycine Methyl glycolate Methyl heptanoate 5-Methyl-2-heptanol 5-Methyl-3-heptanone 6-Methyl-5-hepten-2one Methyl hexadecanoate Methyl hexanoate 5-Methyl-2-hexanone 1-Methylhexylamine 1-Methylhydantoin Methylhydrazine Methyl hydrazinocarboxylate Methyl hydrogen glutarate

Formula weight

ROTATED

m269a m270 m271 m272 m273 m274 m275

N-Methylethylenediamine N-Methylformamide N-Methylformanilide Methyl formate 5-Methylfuraldehyde 2-Methylfuran Methyl 2-furoate Methylgermanium tribromide N-Methylglucamine

Formula

LEFT

m264 m265 m266 m267 m268 m269

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m278 m279 m280 m281 m282 m283 m284 m285

Methyl hydrogen hexanedioate Methyl hydrogen succinate Methyl hydroperoxide Methylhydroquinone Methyl 4-hydroxybenzoate Methyl 2-hydroxyisobutyrate Methyl 4-hydroxyphenylacetate 2-Methylimidazole 2-Methylimidazole

HO2C(CH2)4CO2H

160.17

2, 652

HO2CCH2CH2CO2H

132.12

2, 608

1.081

2

15 4

CH3OOH CH3C6H3 91,4-(OH)2 HOC6H4CO2CH3

48.04 124.14 152.15

1 , 270 6, 874 10, 158

1.997

(CH3)2C(OH)CO2CH3

118.13

32, 223

1.023

HOC6H4CH2CO2CH3

166.18

10, 191

82.11 82.11

23, 46 23, 65

1.440120

8–9

16210mm

56–59

15120mm

15

1.3642

1.411220

1.496020

1.269

m259

misc aq, alc, eth; s bz

270 dec 42

v s alc, eth, acet; 0.25 aq v s aq, alc

92

misc aq

57–60

1635mm

⫺60 142–143

198 268

Methyl isobutenyl ketone, m370 Methyl isobutyl ketone, m367 Methyl isonicotinate, m413 Methyl isopentyl ketone, m271 2-Methyllactic acid, h138

m259a

RIGHT

m258

38

127

Methyl hydroxyacetate, m265 Methyl 2-hydroxypropionate, m296 2,2⬘-Methyliminodiethanol, m230 2,2⬘-Methyliminobis(acetaldehyde diethyl acetal), b176 Methyl iodide, i37 Methyl isoamyl ketone, m271

Methyl 2-furancarboxylate, m259a 5-Methylfurfural, m258 Methyl gallate, m454 ␣-Methyl-D-glucopyranoside, m262 N-Methylguanidine acetic acid, c301 4-Methylhexahydrophthalic anhydride, m204

s alc v s aq, alc, eth

65mm

128–130 126–128

1.030

⬎110

DEAN 37261 (McGHP)

m277

m261

ROTATED

m262

m273

m280

m284

m285

INTERACTIVE

Name

m286 m287 m288 m289

4-Methylimidazole 2-Methyl-1H-indole 2-Methylindoline N-Methylisatoic anhydride Methyl isobutyrate Methyl isocyanate Methyl isodehydracetate N-Methylisopropylamine Methyl isothiocyanate 5-Methylisoxazole Methyl lactate Methyl mandelate Methyl mercaptoacetate Methyl 3-mercaptopropionate Methyl methacrylate

m290 m291 m292 m293

1.270

m294 m295 m296 m297 m298 m299 m300 m301

m304 m305 m306

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

82.11 131.18 133.19 177.16

23, 69 20, 311 20, 279 27, 265

(CH3)2CHCO2CH3 CH3NCO

102.13 57.05 182.18

2, 290 4, 77 18, 410

0.89120 0.967

1.384020 1.369520

⫺84.7 ⫺45 68–70

(CH3)2CHNHCH3

73.14

41, 153

0.702

1.384020

50–53

4, 77 27, 16 3, 280 10, 202

1.069 1.018 1.08820 4 1.175620 1.187

1.525837 1.438620 1.413120

35

CH3CH(OH)CO2CH3 C6H5CH(OH)CO2CH3 HSCH2CO2CH3

73.12 83.09 104.10 166.18 106.14

HSCH2CH2CO2CH3

120.17

32, 214

H2C"C(CH3)CO2CH3

100.12

CH3SO2OCH3

CH3NCS

1.0720 4 1.023

53–56 58–60 1.568120

Boiling point,⬚C 263 273 229

Flash point,⬚C

Solubility in 100 parts solvent

⬎110 v s alc, eth; s hot aq 93

165 dec 92.5 39 16714mm

3 ⫺6

⫺31

1.465720

118 122 144–145 13512mm 4310mm

32 30 49 ⬎110 30

1.085

1.466020

5514mm

60

22, 398

0.943320

1.414020

100

10

110.13

4, 4

1.294320 4

1.413820

202–203

104

CH3OCH2CO2CH3 CH3OCH2COCH2CO2CH3

104.11 146.14

3, 236 34, 1939

1.051120 4 1.129

1.396420 1.431620

130 898.5mm

35 89

CH3OC6H4CO2CH3

166.18

10, 71

1.157

1.533520

248

⬎110

CH3OC6H4CO2CH3

166.18

10, 159

245

⬎110

CH3OC6H4CH2CO2CH3

180.20

10, 191

1.135

1.516520

15819mm

36

CH3OCH2CH2CO2CH3

118.13

3, 297

1.009

1.4020

142–143

47

54–56

⫺48

51

misc alc, eth; sl s aq s aq

v s alc, eth; sl s aq s aq (dec), alc, eth s aq, alc, bz, chl s alc, eth

1,6 aq; s ketones, esters, CCl4 20 aq; 100 DMF v s alc, eth; sl s aq

INTERACTIVE

m307

Formula weight

ROTATED

m302 m303

Methyl methanesulfonate Methyl methoxyacetate Methyl 4-methoxyacetoacetate Methyl 2-methoxybenzoate Methyl 4-methoxybenzoate Methyl 4-methoxyphenylacetate Methyl 4-methoxypropionate

Formula

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m309 m310 m311 m312 m313

m314

1-Methyl-4-(methylamino)piperidine Methyl 2-methylbenzoate Methyl 3-methylbenzoate Methyl 4-methylbenzoate Methyl 2-methylbutyrate 2-Methyl-6-methylene2-octanol

128.22 CH3C6H4CO2CH3

150.18

9, 463

CH3C6H4CO2CH3

150.18

9, 475

CH3C6H4CO2CH3

150.18

9, 484

C2H5CH(CH3)CO2CH3

116.16

2, 304

C2H5C("CH2)(CH2)3C(CH3)2OH

Methyl 2-methyl-3furancarboxylate

1.271

Methyl mercaptan, m37 Methylmercaptoanilines, m436 4-Methylmercaptobenzaldehyde, m437

0.882

1.467220

1.073

1.519020

1.063

20

207–208

1.5160

33–36

82

27mm

113

95

10415mm

90

0.885

1.393120

115

32

156.27

0.784

1.443120

8410mm

76

140.14

1.116

1.473020

7520mm

63

2-Methyl-2-methoxypropane, b572 7-Methyl-3-methylene-1,6-octadiene, m467 1-Methyl-4-(1-methylethenyl)cyclohexane, d736

m287

m288

sl s aq; misc alc, eth

5-Methyl-2-(1-methylethyl)cyclohexanol, m12 5-Methyl-2-(1-methylethyl)cyclohexanone, m13

m289

RIGHT

m286

55

DEAN 37261 (McGHP)

m308

ROTATED

m292

m295

m308

m314

INTERACTIVE

Methyl S-methylthiomethyl sulfoxide Methyl 3-(methylthio)propionate 4-Methylmorpholine 1-Methylnaphthalene 2-Methylnaphthalene Methyl 1-naphthaleneacetate 2-Methyl-1,4-naphthoquinone Methyl 1-naphthyl ketone Methyl 2-naphthyl ketone Methyl nitrate Methyl nitrite N-Methyl-4-nitroaniline 2-Methyl-3-nitroaniline 2-Methyl-4-nitroaniline 2-Methyl-5-nitroaniline 4-Methyl-2-nitroaniline Methyl 2-nitrobenzoate Methyl 3-nitrobenzoate Methyl 4-nitrobenzoate

m316 m317 m318 m319 m320 m321 m322

1.272

m323 m324 m325 m326 m327 m328 m329 m330 m331 m332 m333

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

CH3S("O)CH2SCH3

124.22

1.191

1.548720

952.5mm

⬎110

CH3SCH2CH2CO2CH3

134.20

1.077

1.465020

7513mm

72

C10H7CH3 C10H7CH3 C10H7CH2CO2CH3

101.15 142.20 142.20 200.24

27, 6 5, 566 5, 567 93, 3206

0.920 1.020220 1.02920 4 1.142

1.434920 1.617020 1.602640 1.596120

116 245 241 1625mm

23 82 97 ⬎110

172.18

72, 656

C10H7COCH3

170.21

7, 401

C10H7COCH3

170.21

7, 402

CH3ONO2 CH3ONO O2NC6H4NHCH3

77.04 61.04 152.15

1, 284 1, 284 12, 714

CH3C6H3(NO2)NH2

152.15

12, 848

CH3C6H3(NO2)NH2

152.15

12, 846

CH3C6H3(NO2)NH2

152.15

CH3C6H3(NO2)NH2

⫺66 ⫺30.4 34.4

105–107 1.133604

1.207520 4 0.991(lq)

1.628420

1.374820

Solubility in 100 parts solvent

s aq, alc, eth v s alc, eth v s alc, eth

1.4 alc; 10 bz; s chl

11

302

⬎110

s alc, eth; i aq

53–55

301

⬎110

sl s alc; s CS2

⫺83

64 expl ⫺17.3

sl s aq; s alc, eth s alc, eth

152–154 88–90 1.1586140 4

305

131–133

v s alc; s bz

12, 844

104–107

s alc, acet, eth

152.15

12, 1000

115–116

v s alc; s eth

O2NC6H4CO2CH3

181.15

9, 372

O2NC6H4CO2CH3

181.15

O2NC6H4CO2CH3

181.15

⫺13

1060.1mm

9, 378

78–80

279

9, 390

94–96

1.280

1.534020

⬎110

s alc, eth

INTERACTIVE

m315

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m335 m336 m337 m338 m339 m340 m341 m342

1.273

m343 m344 m345

m346

2-Methyl-3-nitrobenzoic acid 3-Methyl-4-nitrobenzoic acid 4-Methyl-3-nitrobenzoic acid 5-Methyl-2-nitrobenzoic acid 2-Methyl-5-nitroimidazole 3-Methyl-4-nitrophenol 4-Methyl-2-nitrophenol 2-Methyl-2-nitro-1propanol 2-Methyl-2-nitropropyl methacrylate N-Methyl-N-nitroso-4toluenesulfonamide Methyl 2-nonynoate Methyl-5-norbornene2,3-dicarboxylic anhydride Methyl octadecanoate

CH3C6H3(NO2)CO2H

181.15

9, 471

182–184

CH3C6H3(NO2)CO2H

181.15

9, 481

216–218

CH3C6H3(NO2)CO2H

181.15

9, 502

187–190

CH3C6H3(NO2)CO2H

181.15

9, 482

134–136

127.10

231, 23

252–254

CH3C6H3(NO2)OH

153.14

6, 386

127–129

CH3C6H3(NO2)OH

153.14

6, 412

O2NC(CH3)2CH2OH

119.12

1, 378

H2C"C(CH3)CO2CH2C(CH3)2NO2 CH3C6H4SO2N(CH3)NO

187.20

23, 1288

214.24

111, 29

CH3(CH2)5C#CCO2CH3

168.24 178.19

2, 490 172, 461

CH3(CH2)16CO2CH3

298.51

2, 379

1.087

1.57440

32–35

12522mm

86–89

9510mm

1.450020

108

v s alc, eth 350 aq

1024mm

⬎110

12120mm

100 ⬎110

21515mm

⬎110

62 0.915 1.232

1.448420 1.506020

38

Methyl myristate, m428 Methyl nicotinate, m412

4-Methyl-3-nitroanisol, m95 Methyl nonyl ketone, u9

s alc, eth

RIGHT

Methyl 2-methyllactate, m282 Methyl methyl-2-propenoate, m290 Methyl methylsulfinylmethyl sulfide, m315

1.24040 4

DEAN 37261 (McGHP)

m334

ROTATED

m321

m338

m345

INTERACTIVE

m317

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

CH3(CH2)7CH"CH(CH2)7CO2CH3 (CH3)2C"CH(CH2)3CH"CH2 CH3(CH2)6CO2CH3 CH3(CH2)4C#CCO2CH3

m364 m365 m366 m367

Methyl cis-9-octadecenoate 7-Methyl-1,6-octadiene Methyl octanoate Methyl 2-octynoate 3-Methyl-2oxazolidinone 2-Methyl-2-oxazoline 3-Methyl-3-oxetanemethanol Methyl 2-oxocyclopentanecarboxylate Methyl 2-oxopropionate trans-2-Methyl-1,3pentadiene 2-Methylpentane 3-Methylpentane 2-Methyl-1,5-pentanediamine 2-Methyl-2,4pentanediol 4-Methylpentanenitrile Methyl pentanoate 2-Methylpentanoic acid 2-Methyl-1-pentanol 3-Methyl-3-pentanol 4-Methyl-2-pentanol 4-Methyl-2-pentanone

m368

2-Methyl-2-pentenal

CH3CH2CH"C(CH3)CHO

m352 m353 m354

1.274

m355 m356 m357 m358 m359 m360 m361 m362 m363

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

1682mm

⬎110

143–144 192.9 217–220 901mm

26 72 88 ⬎110

1.434020 1.446020

110 8040mm

20 98

1.145

1.456020

10519mm

⬎110

3, 616

1.130

1.406520

134–137

39

82.15

1, 255

0.718

1.446920

75–76

⫺12

CH3CH2CH2CH(CH3)2 (CH3CH2)2CHCH3 H2N(CH2)3CH(CH3)CH2NH2

86.18 86.18 116.21

1, 148 1, 149 4, 270

0.653220 0.664320 0.860

1.372520 1.376520 1.459020

⫺154 ⫺163 80

60.3 63

⬍⫺29 ⬍⫺7

(CH3)2C(OH)CH2CH(OH)CH3

118.18

1, 486

0.921620 4

1.427020

⫺50

198

102

misc aq

(CH3)2CHCH2CH2CN CH3(CH2)3CO2CH3 CH3CH2CH2CH(CH3)CO2H

97.16 116.16 116.16

2, 329 2, 301 22, 288

0.803520 4 0.875 0.924220 20

1.406120 1.396220 1.413520

⫺51.1 ⫺85

156.5 128 196.4

45 22 107

s alc; misc eth sl s aq; misc alc, eth 1.3 aq

CH3CH2CH2CH(CH3)CH2OH (CH3CH2)2C(CH3)OH (CH3)2CHCH2CH(OH)CH3 (CH3)2CHCH2COCH3

102.18 102.18 102.18 100.16

1, 409 1, 411 1, 410 1, 691

0.826220 0.828120 0.808020 0.797820

1.418020 1.418620 1.411220 1.395820

⫺23.6 ⫺90 ⫺84

148 123 132 116.5

54 46 41 18

14, 3471

0.861

1.450320

138

31

s alc, eth misc alc, eth; sl s aq 1.6 aq 1.7 aq; misc alc, bz, eth s alc

296.50

2, 467

0.83920

1.452120

124.23 158.24 154.21 101.11

14, 1049 2, 348 2, 487

0.753 0.877520 4 0.920 1.170

1.436020 1.416025 1.446020 1.454120

85.11 102.13

27, 13 173, 1128

1.005 1.024

(O")C5H7CO2CH3

142.16

10, 597

CH3C("O)CO2CH3

102.09

CH3CH"CHC(CH3)"CH2

98.15

⫺19.9

Boiling point,⬚C

⫺40 15

misc abs alc, eth

v s alc, eth; i aq

misc alc, eth; sl s aq

INTERACTIVE

m347 m348 m349 m350 m351

Formula

ROTATED

Name

LEFT

No.

m370 m370a m371 m372 m373 m374 m375 m376 m377 m378

1.275

m379

4-Methyl-2-pentenoic acid 4-Methyl-3-penten-2one 4-Methyl-2-pentyl acetate 1-Methylpentylamine 3-Methyl-1-pentyn-3-ol

(CH3)2CHCH"CHCO2H

4-Methylphenetole N-(4-Methylphenyl)acetamide Methyl phenylacetate 2-Methyl-1-phenyl-2propanol 1-Methyl-3-phenylpropylamine 3-Methyl-1-phenyl-2pyrazolin-5-one Methyl phenyl sulfide

(CH3)2C"CHCOCH3

114.14

22, 406

0.9529

1.4489

35

11520mm

46

i aq; v s alc

98.15

1, 736

0.865320

1.444020

⫺59

129.5

31

3.1 aq

25

20

147.5

45

⫺19 ⫺30.6

116–118 122

13 26

189–191 307

70

150–153

25–26

218 9618mm

90 81

222

97

(CH3)2CHCH2CH(CH3)O2CCH3

144.21

0.8805

1.3980

CH3(CH2)3CH(NH2)CH3 CH3CH2C(CH3)(OH)C#CH

101.19 98.15

4, 190 12, 506

0.76720 4 0.868820 4

1.431820

CH3C6H4OCH2CH3 CH3C6H4NHCOCH3

136.19 149.19

6, 393 12, 920

0.945 1.21215

1.504420

C6H5CH2CO2CH3 CH6H5CH2C(CH3)2OH

150.18 150.22

9, 434 6, 523

1.044 0.974

1.507520 1.514020

C6H5CH2CH2CH(CH3)NH2

149.24

12, 1165

0.922

1.512320

174.20

24, 20

124.21

6, 297

C6H5SCH3

Methyl octyl ketone, d19 Methyl oleate, m347 o-Methylolphenol, h106 2-Methyloxacyclopropane, p232 Methyl oxirane, p232

1.058

Methyl palmitate, m269a Methyl pentyl ketone, h14 Methylphenols, c303 thru c305 Methyl-m-phenylene diisocyanate, t171

1.588220

129–130

287265mm

⫺15

188

s aq, alc, PE 13 aq, misc bz, acet PE, EtOAc; s eth s alc, EtOAc, HOAc

57

DEAN 37261 (McGHP)

m369

i aq; misc alc, eth

i aq; s alc

Methyl phenyl ether, m55 Methyl phenyl ketone, a31 2-Methyl-2-phenylpropane, b523 Methyl ␥-picolinate, m413

RIGHT ROTATED

m351

m352

m353

m378

INTERACTIVE

Beilstein reference

Density, g/mL

Refractive index

1.074

1.514920

0.903

1.465520

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

Name

m380

N-Methyl-N-phenylurethane N-Methylpiperazine 2-Methylpiperazine N-Methylpiperidine 2-Methylpiperidine 3-Methylpiperidine 4-Methylpiperidine 1-Methyl-3-piperdinemethanol 1-Methyl-4-piperidone 2-Methylpropanaldehyde 2-Methylpropane

C6H5N(CH3)CO2CH2CH3

(CH3)3CH

58.12

1, 124

N-Methyl-1,3-propanediamine 2-Methyl-1,2-propanediamine 2-Methyl-1,3-propanediol 1-Methyl-1-propanethiol 2-Methyl-1-propanethiol 2-Methyl-2-propanethiol 2-Methyl-1-propanol 2-Methyl-2-propanol 2-Methylpropene 2-Methyl-2-propen1-ol Methyl propionate

H2NCH2CH2CH2NHCH3

88.15

41, 419

0.844

1.446820

(CH3)2C(NH2)CH2NH2

88.15

4, 266

0.841

1.441020

HOCH2CH(CH3)CH2OH

90.12

1, 480

1.015

1.445020

⫺91

12520mm

⬎110

CH3CH2CH(SH)CH3

90.19

1, 373

0.824625 4

1.433825

⫺165

84–85

21

sl s aq; v s alc, eth

(CH3)2CHCH2SH

90.19

1, 378

0.835720

1.439620

⫺79

88.5

⫺9

v s alc, eth

(CH3)3CSH

90.19

1, 383

0.794325 4

1.419825

1.1

64.1

⫺4

i aq

(CH3)2CHCH2OH (CH3)3COH (CH3)2C"CH2 H2C"C(CH3)CH2OH

74.12 74.12 56.11 72.11

1, 373 1, 379 1, 207 1, 443

0.801620 0.788820 0.6266mp 4 0.857

1.395820 1.387720

⫺108 25.8 ⫺140

108 82.4 ⫺6.9 113–115

28 11

10 aq; misc alc, eth misc aq, alc, eth v s alc, eth

CH3CH2CO2CH3

85.11

2, 239

0.91520 4

1.377020

79.7

6

m381 m382 m383 m384 m385 m386 m387 m388 m389

1.276

m390 m391 m392

m394

m396 m397 m398 m399 m400

⫺5

138 155.6 106–107 119 126 124 140–145

42 65 3 8 17 7 94

1.461420 1.372720

⫺65

64.1

60 ⫺40

1.3810⫺25

⫺138

⫺11.7

⫺87

139–141

35

100.17 100.17 99.19 99.19 99.19 99.19 129.20

23, 17 20, 19 20, 95 20, 100 20, 101 212, 8

0.816 0.844 0.845 0.838 1.013

1.437820 1.445920 1.447020 1.445820 1.477220

113.16 72.11

212, 215 1, 671

0.920 0.789120

65–67

v s aq, alc, eth 78 aq; 37 acet; 32 bz v s aq; misc alc, eth v s aq; misc alc, eth v s aq v s aq

9 aq; misc alc, bz, chl, eth 13 mL aq; 1320 mL alc; 2890 mL eth

23

1.426020 ⫺88

33 6 aq; misc alc, eth

INTERACTIVE

m401

(CH3)2CHCHO

⬎110

12, 417

ROTATED

m395

C5H10NCH3 CH3C5H9N CH3C5H9N CH3C5H9N

243–244

179.22

LEFT

m393

Formula

Formula weight

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m403 m404 m405 m406 m407 m408 m409 m410 m411 m412 m413

1.277

m414

Methyl propionylacetate 4⬘-Methylpropiophenone Methyl propyl ether 2-Methyl-2-propyl1,3-propanediol Methyl propyl sulfide Methyl 2-propynyl ether 2-Methylpyrazine 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine Methyl 3-pyridinecarboxylate Methyl 4-pyridinecarboxylate 1-Methyl-2-pyridone

C2H5COCH2CO2CH3

130.15

33, 1212

1.037

1.422020

CH3C6H4COCH2CH3

148.21

7, 317

0.993

1.528020

CH3CH2CH2OCH3 CH3CH2CH2C(CH3)(CH2OH)2

745mm

71

7.2

238–239

96

58–60

232

39.1 ⬎110

20

74.12 132.20

1, 354 11, 254

0.738

CH3SCH2CH2CH3 CH3OCH2C#CH

90.18 70.09

13, 1432 1, 4541

0.842420 0.830

1.444220 1.396120

⫺113.0

95.5 62

CH3C5H4N CH3C5H4N CH3C5H4N (C5H4N)CO2CH3

94.12 93.13 93.13 93.13 137.14

23, 94 20, 234 20, 239 20, 240 22, 39

1.030 0.944320 0.956620 0.954820

1.504220 1.495720 1.504020 1.503720

⫺29 ⫺66.7 ⫺18.3 3.8 39

135 129 144 145 209

50 39 36 57

(C5H4N)CO2CH3

137.14

22, 46

1.001

1.512220

8.5

207–209

82

109.13

21, 268

1.112

1.569020

30–32

250740mm

⬎110

s aq ⫺18

2-Methyl-2-propylamine, b511 2-Methylpropylamine, i66 (1-Methylpropyl)benzene, b522 (2-Methylpropyl)benzene, i67 2-Methylpropyl formate, i69 Methyl propyl ketone, p42 2-Methylpropyl-2-methylpropanoate, i70 Methyl pyridyl ketones, a53, a54, a55

v s aq, alc, eth misc aq; s alc, eth misc aq, alc, eth misc aq, alc, eth s aq, alc, bz

RIGHT

2-Methylpropenoic acid, m29 2-Methylpropionaldehyde, i79 2-Methylpropionamide, i70 2-Methylpropionic acid, i81 2-Methylpropionic anhydride, i82 2-Methylpropionitrile, i83 1-Methylpropyl acetate, b502 2-Methylpropyl acetate, i63

Methylpiperidinol, h152 Methyl pivalate, m235 2-Methyl-1-propanamine, i66 2-Methyl-2-propanamine, b511 1-Methyl-1-propanethiol, b471 Methyl propargyl ether, m407 2-Methyl-2-propenenitrile, m30a Methyl propenoate, m126

sl s aq; misc alc, eth

DEAN 37261 (McGHP)

m402

ROTATED

m381

m382

m387

m388

m408

m414

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No. m415 m416

m417 m418 m419

1.278

m420 m421 m422 m423 m424

m430

m432 m433 m434 m435

152.15

Beilstein reference

C6H5C(CH3)"CH2 CH3C6H4CH"CH2 HO2CCH2CH162CO2CH3 CH3(CH2)12CO2CH3

Refractive index

223, 4076

195.26

HOC6H4CO2CH3

Density, g/mL

Melting point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

121–123 1.052

1.515020

⬎110

81.12 85.15 99.13

20, 163 20, 4 21, 237

0.914 0.81920 4 1.027925

1.487520 1.424720 1.468025

⫺57

143.19 143.19 143.19 144.18 152.15

20, 387 20, 395 20, 397 231, 44 10, 70

1.058 1.082620 4 1.063 1.118 1.183120

1.610820 1.620020 1.614020 1.615620 1.536020

⫺2 9–10

118.18 118.18 132.12 242.40 86.13

5, 484 5, 485 2, 608 22, 326 17, 12

0.909 0.897

1.537520 1.541220

⫺24

0.855 0.855220

1.436220 1.405620

100.16

173, 77

0.863

134.20

Boiling point,⬚C

112–113 80–81 202

15 ⫺21 96

i aq; misc alc, eth misc aq, eth misc aq, alc, bz, eth

248 263 259 245–247 223

79 ⬎110 ⬎110 107 96

i aq; s chl, eth misc alc, bz, eth

165.5 170–175 15120mm 323 78

45 45 ⬎110 ⫺11

1.420420

109733mm

6

1.191

1.477220

276

⬎110

20

134 1357mm

32 ⬎110

145 6315mm

37 67

16516mm

⬎110

99.16 143.21

27.16 27,3, 1754

1.090 1.196

1.5257 1.550820

101.17 87.14

27, 13

CH3SCH2CN

1.067 1.039

1.520020 1.482620

CH3SC6H4NH2

139.22

131, 141

1.130

1.642320

⫺24.4

180 ⫺8

56–59 18.4

⫺101

misc aq 0.7 aq; misc alc, HOAc; s chl, eth

misc alc, bz, eth

INTERACTIVE

m436

␣-Methylstyrene 4-Methylstyrene mono-Methyl succinate Methyl tetradecanoate 2-Methyltetrahydrofuran 3-Methyltetrahydropyran 3-Methyltetrahydrothiophene-1,1-dioxide 4-Methylthiazole 4-Methyl-5-thiazoleethanol 2-Methyl-2-thiazoline (Methylthio)acetonitrile 3-(Methylthio)aniline

Formula weight

ROTATED

m431

Methyl 3-pyridylcarbamate 2-[3-(6-Methyl-2pyridyl)propoxy]ethanol N-Methylpyrrole N-Methylpyrrolidine N-Methyl-2pyrrolidinone 2-Methylquinoline 4-Methylquinoline 6-Methylquinoline 2-Methylquinozaline Methyl salicylate

Formula

LEFT

m425 m426 m427 m428 m429

Name

m438 m439 m440 m441 m442

4-(Methylthio)benzaldehyde 2-(Methylthio)benzothiazole 3-(Methylthio)-2butanone Methyl thiocyanate 2-Methylthiophene 3-Methylthiophene

CH3SC6H4CHO

CH3CH(SCH3)COCH3

152.22

81, 533

181.28

27, 109

118.20

CH3SCN

73.12 98.17 98.17

1-Methyl-2-(3-pyridyl)pyrrolidine, n19 Methyl pyruvate, m355 Methyl stearate, m346

1.144

1.645220

1 , 3993

0.975

20

1.4710

3, 175 17, 37 17, 38

1.06820 1.019320 1.021820

1.468020 1.519920 1.518020

4

⬎110

901mm

⬎110

43–46

Methyl succinyl chloride, m195 Methylsulfonic acid, m34 Methyl theobromine, c1

20mm

⫺5 ⫺63 ⫺69

50–54

44

133 113 115.4

38 7 11

i aq; misc alc, eth i aq; misc alc, eth

Methyl thienyl ketone, a57 Methyl thioglycolate, m298

DEAN 37261 (McGHP)

m437

1.279 m415

m416

m417

m418

m419

m420

RIGHT

m421

m422

m423

m429

m430

m431

ROTATED

m432

m433

m434

m438

m441

m442

INTERACTIVE

5-Methyl-2-thiophenecarboxaldehyde N-Methyl-2-thiourea N-Methyl-o-toluamide N-Methyl-p-toluenesulfonamide Methyl p-toluenesulfonate Methyltriacetoxysilane Methyl trichloroacetate Methyltrichlorosilane Methyltriethoxysilane Methyl trifluoroacetate Methyl trifluoromethanesulfonate Methyl 3,4,5-trihydroxybenzoate Methyltrimethoxysilane Methyl trimethylacetate N-Methyl-N-(trimethylsilyl)trifluoroacetamide (Methyl)triphenylphosphonium bromide 2-Methylundecanal Methyl urea N-Methyl–N-vinylacetamide

m444 m445 m446 m447 m448 m449

1.280

m450 m451 m452 m453 m454 m455 m456 m457

m458

m459 m460 m461

Formula weight

Beilstein reference

Density, g/mL

Refractive index 1.586020

Melting point,⬚C

Boiling point,⬚C 11425mm

Flash point,⬚C

126.18

171, 151

1.170

CH3NHC("S)NH2 CH3C6H4CONHCH3 CH3C6H4SO2NHCH3

90.15 149.19 185.25

4, 70 9, 465 11, 105

1.15815

119–121 69–71 76–79

CH3C6H4SO2OCH3

186.23

11, 99

1.234

27.5

1455mm

⬎110

CH3Si(O2CCH3)3 Cl3CCO2CH3

220.26 177.42

43, 1896 2, 208

1.17520 4 1.488

1.40820 1.455820

40–45

883mm 153

85 72

CH3SiCl3 CH3Si(OCH3)3 F3CCO2CH3

149.48 178.30 128.05

43, 1896 4, 629 23, 427

1.273 0.895 1.273

1.411020 1.384020 1.290720

66 141–143 43

⫺15 23 ⫺7

F3CSO2OCH3

164.10

34, 34

1.450

1.324420

94–99

38

(HO)3C6H2CO2CH3

184.15

10, 483

CH3Si(OCH3)3

136.22

44, 4203

0.955

1.370320

102

11

(CH3)3CCO2CH3

116.16

2, 320

0.873

1.390020

101

6

F3CC("O)N(CH3)Si(CH3)3

199.25

1.075

1.380220

132

25

[CH3P(C6H5)3]⫹ Br⫺

357.24

16, 760

CH3(CH2)8CH(CH3)CHO CH3NHCONH2 CH3CON(CH3)CH"CH2

184.32 74.08 99.13

171

93

4, 64 43, 442

7025mm

58

Solubility in 100 parts solvent

82 v s aq, alc

201–203

230–234

0.83015 4 1.204 0.959

1.432120 101–102 1.482920

s alc, eth v s aq, alc; i eth

INTERACTIVE

m443

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

m467

Methyl vinyl ether Morpholine 4-Morpholinepropionitrile N-Morpholino-1-cyclohexene 3-(N-Morpholino)-1,2propanediol Myrcene

n1 n2

1-Naphthaldehyde Naphthalene

n3

1-Naphthalenecarboxylic acid 1,5-Naphthalenediamine 1,8-Naphthalenediamine

m465 m466

n4 n5

CH3OCH"CH2

0.751120 4 1.000520 1.037

1.3947 1.454820 1.471520

167.25

0.995

1.512820

161.20

1.157

58.08 87.12 140.19

13, 1857 27, 5 273, 337

⫺123 ⫺4.9 21

5.5 128 1212mm

⫺56 37.5

12010mm

68

19130mm

⬎110

167

39

s alc, chl, eth, HOAc

1–2 80

16115mm 217.7

⬎110 79

300

s alc, eth 0.3 aq; 7 alc; 33 bz; 50 chl sl s aq; v s hot alc, eth

37–38

(CH3)2C"CHCH2CH2C("CH2)CH"CH2 C10H7CHO C10H8

136.24

1, 264

0.801320

1.470920

156.18 128.17

7, 400 5, 531

1.15020 4 1.16220 4

1.652020 1.5821100

C10H7CO2H

172.18

9, 647

160–162

C10H6(NH2)2

158.20

13, 203

185–187

C10H6(NH2)2

158.20

13, 204

1.281

1.682899

66.5

s hot aq, hot alc 20512mm

MSTFA, m457 Myristic acid, t44 Myristolyl chloride, t46 Myristyl alcohol, t45 Myristyl bromide, b36 Naphthacene, b7 1-Naphthaleneacetamide, n13 1-Naphthaleneacetonitrile, n16 1,2-(1,8-Naphthalene)benzene, f1 Naphthalenediols, d439 thru d442

Methyl veratrate, m231 Michler⬘s ketone, b178 Monoethyl adipate, e177 Monoglyme, d505 Monomethyl adipate, m277 Monomethyl glutarate, m276 Monomethyl succinate, m278 4-Morpholinocarboxyaldehyde, f39 1-Morpholinocyclopentene, c403 4-Morpholinoethanol, h127

sl s aq; s alc, eth

RIGHT

4-Methyl-2-thiouracil, h125 Methyl o-toluate, m309 Methyl m-toluate, m311 Methyltrichlorosilane, t242 Methyl trimethylacetate, m235 ␤-Methylumbelliferone, h148 Methyl undecyl ketone, t263 Methyl urethane, m187 Methyl valerate, m362 4-Methylvaleronitrile, m361

1.126599 4

0.8 aq; v s alc misc aq, alc, bz, eth

DEAN 37261 (McGHP)

m462 m463 m464

ROTATED

m443

m463

m464

m465

m466

INTERACTIVE

No. n6 n7

n8 n9 n10 n11 n12

Name 1-Naphthalenesulfonic acid 2-Naphthalenesulfonic acid 1,8-Naphthalic anhydride 1-Naphthol 2-Naphthol

1.282

Density, g/mL

Refractive index

Melting point,⬚C

C10H7SO3H

208.24

11, 155

C10H7SO3H

208.24

11, 171

198.18

17, 521

C10H7OH C10H7OH

144.17 144.17

6, 596 6, 627

1.095499 4 1.2174

158.16 202.21

7, 724 6, 645

1.422

C10H7OCH2CO2H C10H7CH2ONH2

185.23

9, 666

182

C10H7O2CCH3 C10H7CH2CO2H C10H7CH2CN C10H7NH2 C10H7NCO

186.21 186.21 167.21 143.18 169.19 162.24

6, 608 9, 666 9, 667 12, 1212 12, 1244 23, 117

1.619220 1.6703 1.634420 1.588220

43–46 135 33–35 50 4 ⫺79

191.14 165.15 165.15 138.13 138.13 138.13 151.12 151.12 166.12 166.12 123.11

4, 369 7, 288 7, 288 12, 687 12, 698 12, 711 7, 250 7, 256 9, 373 9, 381 5, 233

1.554615

242 dec 76–78 78–80 71 114 147 58 106–107 174–178 140–143 5.8

N(CH2CO2H)3 O2NC6H4COCH3 O2NC6H4COCH3 O2NC6H4CH2 O2NC6H4CH2 O2NC6H4CH2 O2NC6H4CHO O2NC6H4CHO O2NC6H4CONH2 O2NC6H4CONH2 C6H5NO2

1.12325 25 1.177 1.009720 4

1.620699

Flash point,⬚C

Solubility in 100 parts solvent

90 dehydrates 124 dehydrates

v s aq, alc; sl s eth

268

sl s HOAc

96 123

v s aq, alc

288 285

161

126 155–157

1.44215 1.43 1.43714 1.279220 4 1.496 32 1.462 1.20515 4

Boiling point,⬚C

v s alc, bz, chl, eth 0.1 aq; 125 alc; 6 chl; 77 eth; s alk s bz, chl, eth, hot alc

i aq; s bz, CS2 ⬎110 dec 19418mm 301 267 12317mm

202 202 284 306 332 16423mm

⬎110 157 ⬎110 101

165

317 210.8

88

s alc, eth 3.3 alc; v s chl, eth s alc 0.2 aq; v s alc, eth misc aq; v s alc, eth, PE 0.1 aq; s hot alc s alc, eth s alc s hot aq, alc, chl 0.1 aq; 5 alc; 6 eth 4 alc; 3.3 eth; s bz s alc, chl, eth s alc, bz, HOAc s hot aq, hot alc, eth v s alc, bz, eth

INTERACTIVE

Nitrilotriacetic acid 3⬘-Nitroacetophenone 4⬘-Nitroacetophenone 2-Nitroaniline 3-Nitroaniline 4-Nitroaniline 3-Nitrobenzaldehyde 4-Nitrobenzaldehyde 2-Nitrobenzamide 3-Nitrobenzamide Nitrobenzene

Beilstein reference

ROTATED

n20 n21 n22 n23 n24 n25 n26 n27 n28 n29 n30

n13

Formula weight

LEFT

n14 n15 n16 n17 n18 n19

1,4-Naphthoquinone (2-Naphthoxy)acetic acid 2-(1-Naphthyl)acetamide 1-Naphthyl acetate 1-Naphthylacetic acid 1-Naphthylacetonitrile 1-Naphthylamine 1-Naphthyl isocyanate Nicotine

Formula

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

n32 n33 n34 n35 n36 n37 n38 n39 n40

1.283

n41 n42 n43 n44

3-Nitrobenzene-1,2dicarboxylic acid 5-Nitrobenzene-1,3dicarboxylic acid 2-Nitrobenzenesulfonyl chloride 5-Nitrobenzimidazole 2-Nitrobenzoic acid 3-Nitrobenzoic acid 4-Nitrobenzoic acid 4-Nitrobenzonitrile 3-Nitrobenzoyl chloride 4-Nitrobenzoyl chloride 2-Nitrobenzyl alcohol 3-Nitrobenzyl alcohol 4-Nitrobenzyl alcohol 4-Nitrobenzyl bromide

O2NC6H3(CO2H)2

211.13

9, 823

216 dec

2 aq; v s hot alc

O2NC6H3(CO2H)2

211.13

9, 840

260

0.15 aq; v s alc, eth

O2NC6H4SO2Cl

221.62

11, 67

65–67

s eth; d hot aq, alc

O2NC6H4CO2H O2NC6H4CO2H O2NC6H4CO2H O2NC6H4CN O2NC6H4COCl

163.14 167.12 167.12 167.12 148.12 185.57

23, 135 9, 370 9, 376 9, 389 9, 397 9, 381

207–209 146–148 140–142 242.8 146–149 32–35

275–278

s alc, acid 0.7 aq; 33 alc; 22 eth 0.3 aq; 33 alc; 40 acet 9 alc; 2 eth; 5 acet s HOAC; sl s aq, alc dec aq, alc; v s eth

O2NC6H4COCl

185.57

9, 394

75

205105mm

O2NC6H4CH2OH O2NC6H4CH2OH O2NC6H4CH2OH O2NC6H4CH2Br

153.14 153.14 153.14 216.04

6, 447 6, 449 6, 450 5, 334

70–72 30–32 92–94 98–100

270 1803mm 18512mm

1.58 1.494 1.58

dec aq, alc; s eth

⬎110

Nicotinic acid, p266 Nicotinonitrile, c329 Ninhydrin, i13 Nioxime, c361 2,2⬘,2⬙-Nitrilotriethanol, t266 1,1⬘,1⬙-Nitrilotris(2-propanol), t325 2-Nitro-p-anisidine, m89 5-Nitro-o-anisidine, m90 Nitroanisoles, m81, m92

s aq, alc, eth v s alc, eth; sl s aq 2 alc; v s eth

RIGHT

NBS, b422 Neohexane, d567 Neohexene, d574 Neopentane, d673 Neopentyl alcohol, d676 Neopentyl glycol, d594 Neophyl chloride, c178 Neral, d666 Nicotinaldehyde, p262

1-Naphthol-2-carboxylic acid, h158 3-Naphthol-2-carboxylic acid, h160 1-Naphthonitrile, c327 1-Naphthylamine, a228 N-1-Naphthylaniline, p132 1-Naphthyl bromide, b376 1-Naphthyl chloride, c185 Natural orange 6, h161 NBA, b247

⬎110

DEAN 37261 (McGHP)

n31

ROTATED

n8

n11

n19

n34

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

1.4425 4

1.61325

0.97520 20 1.129625 4

1.4112 1.441420

Melting point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

1.284

n45 n46 n47 n48 n49 n50

4-Nitrobenzyl chloride 2-Nitrobiphenyl 4-Nitrobiphenyl 1-Nitrobutane 3-Nitro-2-butanol 3-Nitrocinnamic acid

O2NC6H4CH2Cl O2NC6H4C6H5 O2NC6H4C6H5 CH3CH2CH2CH2NO2 CH3CH(NO2)CH(OH)CH3 O2NC6H4CH"CHCO2H

171.58 199.21 199.21 103.18 119.12 193.16

n51 n52

2-Nitrodiphenylamine Nitroethane

O2NC6H4NHC6H5 CH3CH2NO2

214.22 75.07

5, 329 5, 582 5, 583 1, 123 1, 373 Merck: 12, 6692 12, 690 1, 99

n53

5-Nitro-2-furaldehyde semicarbazone 1-nitroguanidine 5-Nitro-1H-indazole Nitromethane 1-Nitronaphthalene 3-Nitro-2-pentanol 2-Nitrophenol 4-Nitrophenol 4-Nitrophenyl acetate 2-Nitrophenylacetic acid 4-Nitrophenylacetic acid 4-Nitrophenylacetonitrile 2-Nitro-1,4-phenylenediamine 4-Nitro-1,2-phenylenediamine 4-Nitrophenylhydrazine

198.14

173, 4467

242–244

i aq; s alc 4.5 aq; misc alc, eth; s alk, chl s alk, chl, alk; 0.2 alc

CH3NO2 C10H7NO2 CH3CH2CH(NO2)CH(OH)CH3 O2NC6H4OH O2NC6H4OH O2NC6H4O2CCH3 O2NC6H4CH2CO2H

104.07 163.14 61.04 173.17 133.15 139.11 139.11 181.15 181.15

3, 126 23, 129 1, 74 5, 553 1, 385 6, 213 6, 226 6, 233 9, 454

dec ⬎225 207–209 ⫺28.4 59–60

0.4 aq; sl s MeOH s alc, bz, eth, acet 11 aq; s alc, eth s alc; v s chl, eth

O2NC6H4CH2CO2H

181.15

9, 455

153–155

s alc, bz, eth; sl s aq

O2NC6H4CH2CN

162.15

9, 456

115–117

s alc, eth; i aq

O2NC6H3(NH2)2

153.14

13, 120

137–140

O2NC6H3(NH2)2

153.14

13, 29

199–201

sl s aq; s HCl

O2NC6H4NHNH2

153.14

15, 468

156 dec

s alc, chl, eth, hot bz

n64 n65 n66

47 91

200–201

1.052820 20

1.132225 4 1.223 1.081825 4 1.495 1.270120 4

1.392020

1.379525

76 ⫺90

1.443020 45 113–114 77–79 139–142

8 alc; s eth s alc, acet, CCl4 sl s alc; s chl, eth sl s aq; misc alc, eth 1 alc

114

101.2 304 10010mm 216 279

28

35 90

s alc, bz, eth, alk s aq; v s alc, chl, eth s aq; v s alc, bz, eth s hot aq, alc

INTERACTIVE

n67

179

ROTATED

n63

O2NNHC("NH)NH2

325 340 152.8 9210mm

LEFT

n54 n55 n56 n57 n58 n59 n60 n61 n62

70–73 36.7 112–114 ⫺81.3

Boiling point,⬚C

n69 n70 n71 n72 n73 n74 n75 n76 n77 n78

1.285

n79 n80 n81

2-Nitrophenyl phenyl ether 4-Nitrophenyl phenyl ether 3-Nitro-1,2-phthalic acid 4-Nitro-1,2-phthalic acid 3-Nitrophthalic anhydride 1-Nitropropane 2-Nitropropane 2-Nitro-1-propanol 4-Nitropyridine-Noxide Nitrosobenzene N-Nitrosodimethylamine 4-Nitrosodiphenylamine 1-Nitroso-2-naphthol

⬍ ⫺20

1848mm

6, 232

53–56

320

211.13

9, 823

211.13

9, 828

213–216 dec 170–172

193.11

17, 486

163–165

CH3CH2CH2NO2 (CH3)2CHNO2 CH3CH(NO2)CH2OH O2NC5H4N(:O)

89.09 89.09 105.09 140.10

1, 115 1, 116 1, 358 203, 2528

C6H5NO (CH3)2NNO

107.11 74.08

6, 230 8, 84

C6H5NC6H4NO

198.22

144–145

v s alc, bz, chl, eth

C10H6(NO)OH

173.16

Merck: 12, 6737 7, 712

109–110

377.26

112, 190

⬎300

3 alc; s bz, eth, alk; 0.1 aq 2.5 aq; sl s alc

O2NC6H4OC6H5

215.21

62, 222

O2NC6H4OC6H5

215.21

O2NC6H3(CO2H)2 O2NC6H3(CO2H)2

1-Nitroso-2-naphthol3,6-disulfonic acid disodium salt hydrate

1.000920 0.982120 1.184125 4

1.57520

1.401620 1.394920 1,437920

⫺108 ⫺91.3

s alc, eth ⬎110

s bz, eth

sl s aq, bz 131.1 120.3 9910mm

36 24 100

1.4 aq; misc org solv 1.7 aq; misc org solv s aq, alc, eth

5918mm 151

61

v s aq, alc, eth

159–162 67–69 1.004820 4

Nitroglycerine, g22 5-Nitroisophthalic acid, n32

1.436820

3-Nitrophenyl disulfide, b216 3-Nitro-o-phthalic acid, n31

RIGHT

4-Nitrobenzyl cyanide, n64 Nitrocresols, m339, m340

1.253920

DEAN 37261 (McGHP)

n68

ROTATED

n53

n55

n72

n81

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

123.11

7, 622

n83 n84 n85 n86

2-Nitrotoluene 3-Nitrotoluene 4-Nitrotoluene 2-Nitro-␣,␣,␣-trifluorotoluene 3-Nitro-␣,␣,␣-trifluorotoluene 5-Nitrouracil Nonadecane Nonane 1,9-Nonanediamine Nonanedinitrile 1,9-Nonanedioic acid 1,9-Nonanediol Nonanenitrile Nonanoic acid ␥-Nonanoic lactone 1-Nonanol 2-Nonanone 3-Nonanone 5-Nonanone Nonanoyl chloride 3-Nonen-2-one Nonyl aldehyde Nonylamine Nopol Norbornane 2-Norbornanone

CH3C6H4NO2 CH3C6H4NO2 CH3C6H4NO2 CF3C6H4NO2

137.14 137.14 137.14 191.11

5, 318 5, 321 5, 323 52, 251

1.162219 15 1.158120 4 1.392

CF3C6H4NO2

191.11

5, 327

157.09 268.51 128.26 158.29 150.23 188.22 160.26 139.24 158.24 156.23 144.26 142.24 142.24 142.24 176.69 140.23 142.24 143.27 166.26 96.17 110.16

24, 320 1, 174 1, 165 4, 272 2, 709 2, 707 1, 493 2, 354 2, 352 17, 245 1, 423 1, 709 1, 709 1, 710 2, 353 13, 3017 1, 708 4, 198 63, 396 51, 45 7, 57

n87

1.286

n88 n89 n90 n91 n92 n93 n94 n95 n96 n97 n98 n99 n100 n101 n102 n103 n104 n105 n106 n107 n108

CH3(CH2)17CH3 CH3(CH2)7CH3 H2N(CH2)9NH2 NC(CH2)7CN HO2C(CH2)7CO2H HO(CH2)7OH CH3(CH2)7CN CH3(CH2)7CO2H CH3(CH2)8OH CH3(CH2)6COCH3 CH3(CH2)5COCH2CH3 (CH3CH2CH2CH2)2CO CH3(CH2)7COCl CH3(CH2)4CH"CHCOCH3 CH3(CH2)7CHO CH3(CH2)8NH2

Flash point,⬚C

Solubility in 100 parts solvent

126

dec 144

1.547220 1.545920

⫺10 15.5 52 31–32

222 231.9 238 10520mm

106 101 106 95

s aq; v s alc, eth; explodes on contact with conc acid, alk, or fire s alc, bz misc alc, eth; s bz s alc, bz, chl, eth v s alc, bz

1.43616 4

1.471520

⫺2.4

200–205

87

s alc, eth

0.777632 4 0.717620 4

1.433538 1.405420

⬎300 32 ⫺53.5 37–38

1.446020

168 31 ⬎110 ⬎110

s eth; sl s alc s abs alc, eth

0.929 1.02920 4 0.85115 4 0.90620 4 0.976 0.827920 4 0.832 0.821 0.80620 4 0.94615 4 0.848 0.82719 19 0.782 0.973

1.426020 1.433020 1.447520 1.433820 1.421020 1.420420 1.419020 1.437720 1.448420 1.424020 1.433020 1.493020

330 150.8 258 17611mm 286100mm 17715mm 224.0 254.5 1226mm 215 192743mm 187–188 186–187 215.4 8512mm 185 201 230–240 168–172

33

106.5 47–49 ⫺34.2 12.5 ⫺5.5 ⫺21 ⫺50 ⫺60.5

82–84 94–96

⬎110 81 100 ⬎110 75 64 67 60 95 81 63 62 98

v s alc, bz, eth 0.24 aq; v s alc; 3 eth s alc, eth s alc, chl, eth 0.6 aq; misc alc, eth

misc alc, eth dec aq, alc; s eth

sl s aq; s alc, eth s alc

INTERACTIVE

HOC6H4NO

Boiling point,⬚C

ROTATED

4-Nitrosophenol

Melting point,⬚C

LEFT

n82

Refractive index

n110 o1 o2 o3 o4 o5

o6 o7 o8 o9 o10

exo-2-Norbornyl formate (⫹)-Norephedrine cis,cis-9,12-Octadecadienoic acid Octadecanamide Octadecane 1-Octadecanethiol Octadecanoic acid

1.287

1-Octadecanol 9,12,15-Octadecatrienoic acid 1-Octadecene 9-Octadecen-1-amine cis-9-Octadecenoic acid

140.18

6,3, 219

1.048

1.462220

C6H5CH(OH)CH(CH3)NH2 CH3(CH2)4CH"CHCH2CH"CH(CH2)7CO2H CH3(CH2)16CONH2 CH3(CH2)16CH3 CH3(CH2)17SH CH3(CH2)16CO2H

151.21 280.44

132, 371 2, 496

0.902520 4

1.469920

51–54 ⫺5

23016mm

283.50 254.50 286.57 284.48

2, 383 1, 173 1,3, 1838 2, 377

0.776728 4 0.84770

1.436728 1.4648 1.429980

102–104 28.2 31–35 69

25112mm 316.3 360 383

CH3(CH2)17OH CH3(CH2CH"CH2)3CH2(CH2)6CO2H CH3(CH2)15CH"CH2 CH3(CH2)7CH"CH(CH2)8NH2 CH3(CH2)7CH"CH(CH2)7CO2H

270.50 278.44

1, 431 2, 499

0.812358 4 0.91418 4

1.438820 1.480020

59.6

20310mm 23017mm

252.49 267.50 282.47

1, 226

0.79118 4 0.813 0.893620 4

1.443920 1.459620 1.458120

17.7

314.9

13.4

360

2, 463

53 ⬎110 v s eth; 10 PE; s abs alc s hot alc, hot eth s acet, eth; sl s alc s eth; sl s alc 4.9 alc; 20 bz; 50 chl; 3.9 acet; 16.6 CCl4; s toluene, pentyl acetate s alc, eth s alc, bz, eth

165 185

⬎110 148 154 189

s hot acet s alc, bz, chl, eth

5-Norbornen-2-carbaldehyde, b136 Norbornene, b135 Norbornylene, b135 Norcamphor, a104 Norleucine, a182 Norvaline, a248 NTA, n20

RIGHT

5-Nitro-o-toluidine, m329 4-Nitroveratrole, d511 Nitroxylenes, d638 thru d641 Nonyl alcohol, n98 Nonyl iodide, i42 2,5-Norbornadiene, b134 exo-2-Norbornanamine, a245

N-Nitrosophenylhydroxylamine, c317 Nitroso-R-salt, n81 3-Nitro-o-toluic acid, m334 3-Nitro-p-toluic acid, m336 4-Nitro-m-toluic acid, m331 6-Nitro-m-toluic acid, m337 2-Nitro-p-toluidine, m330 4-Nitro-o-toluidine, m328

6716mm

DEAN 37261 (McGHP)

n109

ROTATED

n88

n97

n106

n107

n108

n109

INTERACTIVE

No. o11

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

1.288

22, 441

0.85179

1.430899

44-45

288100mm

CH3(CH2)7CH"CH(CH2)8OH CH3(CH2)7CH"CH9(CH2)7COCl

268.49 300.92

1, 453 2, 469

0.85020 4 0.912

1.461020 1.463020

13–19

1958mm 1803mm

⬎110 ⬎110

H2C"CHCO2(CH2)17CH3 CH3(CH2)17NH2 CH3(CH2)17NCO CH3(CH2)17SiCl3

324.55 269.52 299.51 387.94

24, 1468 4, 196 43, 439

0.800 0.77727 0.847 0.984

1.450120 1.460220

23232mm 1735mm 22310mm

⬎110 ⬎110 148 89

CH3(CH2)17OCH"CH2 H2C"CH(CH2)4CH"CH2 HCF2CF2CF2CF2CH2OH

296.54 110.20 232.07

1.444030 1.422020 1.317820

28

14, 1648

0.82130 4 0.746 1.664720

1875mm 114–121 140–141

177 9 75

[-(CH3)2SiO-]4

296.62

43, 1885

0.956

1.395820

17–18

176

60

[(CH3)3SiO]2Si(CH3)2 CH3(CH2)6CH3 H2N(CH2)8NH2 HO2C(CH2)6CO2H CH3(CH2)5CH(OH)CH2OH HO(CH2)8OH CH3(CH2)6CN CH3(CH2)7SH CH3(CH2)6CO2H

236.54 114.23 144.26 174.20 146.23 146.23 125.22 146.30 144.21

43, 1879 1, 159 4, 271 2, 691 13, 2217 1, 490 2, 349 13, 1710 2, 347

0.820020 0.702820 4

1.384820 1.397420

⬎110

1.420220 1.452520 1.427920

153 125.7 225–226 23015mm 13210mm 17220mm 198 199.0 239

29 22 165

0.813520 0.843 0.908820 4

ca. ⫺80 ⫺56.8 50–52 140–144 36–38 59–61 ⫺45.6 ⫺49.2 16.6

⫺15.5

234 195

⬎110 81

175 174–176 176.6 173

71 65 71 52

142.20 130.23

17, 244 1, 418

0.981 0.825820 4

1.444020 1.429020

o33 o34 o35 o36

(⫾)-2-Octanol 3-Octanol 4-Octanol 2-Octanone

CH3(CH2)5CH(OH)CH3 CH3(CH2)4CH(OH)CH2CH3 CH3(CH2)3CH(OH)CH2CH2CH3 CH3(CH2)5COCH3

130.23 130.23 130.23 128.22

1, 419 11, 208

0.819320 4 0.819 0.819220 0.81920 4

1.420220 1.426020 1.42520 1.415020

1, 704

⫺31.6

⫺16

s alc, eth; i aq

s alc, bz, eth

s bz, PE; sl s alc s eth; sl s alc 0.16 aq; 0.6 eth; s alc

73 68 ⬎110

v s alc; sl s aq, eth s eth; sl s alc s alc 0.07 aq; v s alc, chl, eth, PE 0.06 aq; misc alc, chl, eth 0.1 aq; misc, alc, eth

i aq; misc alc, eth

INTERACTIVE

CH3(CH2)7OH

s bz, chl, eth

ROTATED

␥-Octanoic lactone 1-Octanol

o21

32–34 55–57 15–16

Solubility in 100 parts solvent

LEFT

o31 o32

o18 o19 o20

Flash point,⬚C

282.47

o22 o23 o24 o25 o26 o27 o28 o29 o30

o14 o15 o16 o17

Boiling point,⬚C

CH3(CH2)7CH"CH(CH2)7CO2H

trans-9-Octadecenoic acid cis-9-Octadecen-1-ol 9-Octadecenoyl chloride Octadecyl acrylate Octadecylamine Octadecyl isocyanate Octadecyltrichlorosilane Octadecyl vinyl ether 1,7-Octadiene 1H,1H,5H-Octafluoro1-pentanol Octamethylcyclotetrasiloxane Octamethyltrisiloxane Octane 1,8-Octanediamine 1,8-Octanedioic acid 1,2-Octanediol 1,8-Octanediol Octanenitrile 1-Octanethiol Octanoic acid

o12 o13

Melting point,⬚C

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

1.289

o42 o43 o44 o45 o46 o47 o48 o49 o50 o51 o52 o53

3-Octanone 4-Octanone Octanoyl chloride 1-Octene 2-Octen-1-ylsuccinic anhydride Octyl acetate Octyl aldehyde Octylamine Octyl cyanoacetate Octyl gallate 1-Octyl-2-pyrrolidine Octyltrichlorosilane 1-Octyne 1-Octyn-3-ol L-(⫹)-Ornithine Oxalic acid Oxalic acid dihydrate

o54 o55

Oxalyl bromide Oxalyl chloride

CH3(CH2)4COCH2CH3 CH3(CH2)3COCH2CH2CH3 CH3(CH2)6COCl CH3(CH2)5CH"CH2

128.22 128.22 162.66 112.22 210.27

1, 706 1, 706 2, 348 1, 221

0.822020 4 0.809 0.955 0.714920 4 1.000

1.415020 1.413920 1.435020 1.408720 1.469420

CH3CO2(CH2)7CH3 CH3(CH2)6CHO CH3(CH2)7NH2 NCCH2CO2(CH2)7CH3 3,4,5-(HO)3C6H2CO2(CH2)7CH3

2, 134 1, 704 4, 196

0.868 0.82120 4 0.782 0.934

1.418520 1.418320 1.429020 1.449020

CH3(CH2)7SiCl3 CH3(CH2)5C#CH CH3(CH2)4CH(OH)C#CH H2N(CH2)3CH(NH2)CO2H HO2CCO2H HO2CCO2H · 2H2O

172.27 128.22 129.25 197.28 282.34 197.32 247.67 110.19 126.20 132.16 90.04 126.07

43, 1907 1, 258 13, 1996 4, 420 2, 502 2, 502

0.920 1.07020 0.745720 0.864

1.465020 1.447320 1.415920 1.441020

BrC("O)C("O)Br ClC("O)C("O)Cl

215.84 126.93

21, 236 2, 542

1.9017 4 1.65319 4

1.455

Octyl bromide, b385 Octyl chloride, c204 Octyl cyanide, n95 Octyldimethylamine, d649 Octyl ether, d729 Octyl iodide, i44 Octyl sulfide, d730 Oleic acid, o11

1.522020 1.429020

12–15 ⫺5/⫺1 101–104 ⫺25 ⫺79.3 140 190 dec ⫺2H2O, 102 ⫺19 ⫺10

46 45 80 21 ⬎110

211 171 175–177 950.11mm

88 51 62 ⬎110

17215mm 226730mm 126.2 8319mm

⬎110 96 17 63

i aq; misc alc, eth dec aq, alc; s eth i aq; misc alc, eth

sl s aq; misc alc sl s aq; misc alc i aq; s alc, eth

i aq; s alc, eth v s aq, alc; sl s eth 14 aq20; 40 alc; 1.3 eth 14 aq; 40 alc; 1 eth

103720mm 64

none none

Oleoxyl chloride, o13 Oleyl alcohol, o12 Oleylamine, o9 o-Orthanilic acid, a115 7-Oxabicyclo[2.2.1]heptane, c331b, e7 7-Oxabicyclo[4.1.0]heptane, e6 6-Oxabicyclo[3.1.0]hexane, e10 Oxacyclopentane, t69

s eth; viol dec aq, alc

RIGHT

Octadecyl bromide, b384 Octadecyl iodide, i43 Octadecyl mercaptan, o4 2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine, d62 Octaldehyde, o43 Octamethylene glycol, o27 Octanal, o43 1,8-Octanedicarboxylic acid, d10 tert-Octylamine, t103

103, 2079

⬍ ⫺70 ⫺102 8–12

167–168 164 195 121 16810mm

DEAN 37261 (McGHP)

o37 o38 o39 o40 o41

ROTATED

o31

o41

o47

INTERACTIVE

No. o56 o57 o58 o59 o60 o61 o62 o63 o64 o65 o66

1.290

o66a o67 o68 o69

Beilstein reference

118.10 103.08 88.07 87.08 102.09 113.16

2, 559 2, 559 2, 545 27, 135 3, 629 212, 216

CH3CO(CH2)3CN CH3COCH2CH2CO2H CH3C("O)CHO CH3C("O)CO2H

111.14 116.12 72.06 88.06 138.17

33, 1234 3, 671 1, 762 3, 608

(CH3)3COC(CH3)3

130.23

HO2CCH2OCH2CO2H H2NC6H4OC6H4NH2 NCCH2CH2OCH2CH2CN

134.09 200.24 124.14

CH3CH2C("O)CO2H

(CH2O)x

Density, g/mL

Refractive index

1.66720 4 1.20017 4 1.0275 4

1.397220

0.975 1.144725 4 1.045524 15 1.2674 1.120

1.432820 1.439620 1.420920 1.431520 1.488020

0.7658

1.394920

3, 234 13, 441

19, 385 6, 206 1, 690 5, 205 1, 87 5, 247

C6Cl5OH C5Cl5N CH3(CH2)13CH3 CH3(CH2)13CN [CH3(CH2)7]2C"O

266.34 251.33 212.42 223.40 226.40

6, 194 20, 232 1, 172 21, 163 1, 717

33–35 11.8

Boiling point,⬚C

1.404920 1.537025

1, 656 1.834216 1.671225 4 1.71825 4

1.496720 1.503020

1.97822 4 0.768420 4 0.825

1.431920 1.442020

Solubility in 100 parts solvent s hot aq; sl s alc, eth s alk; sl s aq; i eth sl s hot aq, alc

22048mm 8216mm 270

81 125

240 246 72 165 dec 1400.3mm

107 137 none 82 ⬎110

1120.5mm

124 375

190–191 124–126 9.9 20–23 41–43

310

192 275–277 160

270 322 178

v s aq, alc, bz, eth s aq, alc misc aq, alc, eth

v s aq, alc; sl s eth 218 ⬎110 71

12.6 6 223–226 21 (anhyd) 82–85 ⫺29.0 140–143

v s aq, alc; v sl s eth 84 aq; v s alc, eth, chlorinated HC’s

dec acids

dec

165 dec 0.998415 1.2625 4

Flash point,⬚C

107

1.440520

1, 566 132.16 291.27 488.62 230.31 250.34 202.30 295.34

240 dec 218 dec dec 350 86–89 32–34 69.2

142–145 190–192 1.043

[-HC(CH3)O-]3 (C2H5O)2P("S)C6H4NO2 C6Br5OH Cl2CHC("O)CCl3 C6HCl5 Cl2CHCCl3 C6Cl5(NO2)

Melting point,⬚C

none none none

s(slow) aq; s alk; i alc, eth 11 aq; misc alc, chl v s alc, bz, eth sl s alc, eth i aq; v s acet v s bz, chl, eth 0.05 aq; misc alc, eth s bz, chl v s alc; s bz; 148 eth

132 ⬎110 ⬎110

v s alc, eth s alc

INTERACTIVE

p9 p10 p11 p12 p13

Paraldehyde Parathion Pentabromophenol Pentachloroacetone Pentachlorobenzene Pentachloroethane Pentachloronitrobenzene Pentachlorophenol Pentachloropyridine Pentadecane Pentadecanenitrile 8-Pentadecanone

H2NNHC("O)C("O)NHNH2 H2NC("O)C("O)NHNH2 H2NC("O)C("O)NH2

Formula weight

ROTATED

p2 p3 p4 p5 p6 p7 p8

Oxalyl dihydrazide Oxamic hydrazide Oxamide 2-Oxazolidone 2-Oxobutyric acid 2-Oxohexamethyleneimine 5-Oxohexanonitrile 4-Oxopentanoic acid 2-Oxopropionaldehyde 2-Oxopropionic acid 2-Oxo-1-pyrrolidinepropionitrile 2,2⬘-Oxybis[2-methyl]propane 2,2⬘-Oxydiacetic acid 4,4⬘-Oxydianiline 3,3⬘-Oxydipropionitrile Paraformaldehyde

Formula

LEFT

p1

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

p21 p22

p23 p24 p25

1.291

3-Pentadecylphenol 1,2-Pentadiene cis-1,3-Pentadiene trans-1,3-Pentadiene 1,4-Pentadiene Pentaerythritol Pentaerythritol diacrylate monostrearate Pentaerythritol triacrylate Pentaerythrityl tetranitrate

CH3(CH2)14C6H4OH CH3CH2CH"C"CH2 CH3CH"CHCH"CH2 CH3CH"CHCH"CH2 H2C"CHCH2CH"CH2 C(CH2OH)4 CH3(CH2)16CO2CH2C(CH2O2CCH"CH2)2CH2OH (H2C"CHCO2CH2)3CCH2OH

304.52 68.12 68.12 68.12 68.12 136.15 510.72

C(CH2ONO2)4

316.15

12, 602

1.177320 4

Pentaethylenehexamine Pentamethylbenzene 1,2,3,4,5-Pentamethylcyclopentadiene

H2N(CH2CH2NH)4CH2CH2NH2

232.38

44, 1245

0.950

1.509620

C6H(CH3)5

148.25 136.24

5, 443

0.91720 4 0.870

1.52720 1.473320

1, 251 1, 251 1, 251 1, 251 1, 528

298.30

0.692620 4 0.691010 0.676020 0.660822 4 1.3825 4 1.018

1.420920 1.436320 1.430120 1.388820 1.548

1.180

1.486420

50–53 ⫺137.3 ⫺140.8 ⫺87.5 ⫺148.3 260 29–31

⬎110 ⫺28 ⫺28 4 6 aq; v sl s alc; i eth ⬎110

⬎110 140

explodes on shock

s acet; sl s eth, alc

⬎110 54.4

231 5813mm

91 44

Palmitic acid, h34 Pelargonaldehyde, n104 Pelargonic acid, n96 Pelargononitrile, n95 Pelargonoyl chloride, n102 Pentaerythritol diformal, t125 Pentalin, p7 Pentamethylene glycol, p32 Pentamethylene oxide, t83

v s alc, bz

RIGHT

1,1⬘-Oxybis(2-ethoxyethane), b186 1,1⬘-Oxybis(2-methoxyethane), b214 1,1⬘-Oxybis(3-methylbutane), d466a 1,1⬘-Oxybis(2-methylpropane), d458 1,1⬘-Oxybis(pentane), d738 2,2⬘-Oxybis(propane), d476 3,3⬘-Oxybis(1-propene), d31 2,2⬘-Oxydiethanethiol, b208 2,2⬘-Oxydiethanol, b198

Oxapentadiene, f45 Oxetanone, p210 Oxirane, e147 2-Oxo-10-bornanesulfonic acid, c5 3-Oxobutanoic acid, a25 Oxolan-2-one, b617 3-Oxo-N-phenylbutanamide, a24 2,2⬘-Oxybis(chloroethane), b163 1,1⬘-Oxybis(chloromethane), b165a

1951mm 44.9 44.1 42.0 26.0

DEAN 37261 (McGHP)

p14 p15 p16 p17 p18 p19 p20

ROTATED

o59

o61

o66

p25

INTERACTIVE

No. p26

p27

1.292

p28 p29 p30 p31 p32 p33 p34 p35 p36

Beilstein reference

Density, g/mL

Refractive index

0.830

1.442020

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

⫺20

198

59–61

19412mm

1.394220 1.357520 1.459120 1.439720 1.449420 1.406820 1.451020 1.399115

⫺92 ⫺129.7 ⫺129.7

103 36.0 178–180 206 239 110–112 138 141.3

12 ⫺49 62 104 129 19 34 40

1.4 aq; misc alc, eth misc alc, eth s aq, alc; sl s eth

0.840 0.939020 4 0.814620 4 0.809820 4 0.815025 4 0.809520 0.814320 0.988 1.016 1.109

1.446020 1.408020 1.410020 1.405420 1.407725 1.390020 1.392020 1.514320 1.421620 1.465020

⫺75.7 ⫺33.7 ⫺79 ⫺73 ⫺69 ⫺76.8 ⫺39.0

126.6 186 137.5 119.3 116 102 102.0 1075mm 125–127 1350.2mm

18 96 33 34 41 7 13 102 32 ⬎110

i aq; misc alc, eth 2.4 aq; v s alc, eth 2.7 aq22; misc alc, eth 16.6 aq20; misc alc, eth 5.5 aq20; s alc, eth misc acet, bz, eth, PE 3.4 aq s alc, eth

13, 2107

1.008720 4

1.433020

⫺27

275–276

140

1, 210 1, 210 1, 210 22, 400 2, 427

0.642920 4 0.650320 4 0.648220 4 0.820 0.837

1.371420 1.381320 1.379220 1.426920 1.422120

⫺165 ⫺151 ⫺140

30.1 37.0 36.3 128 144–147

⫺18 ⫺20 ⫺45 23 40

s aq; misc hydrocarbon solvents misc alc, bz, eth misc alc, eth misc alc, eth

173.30

4,4, 1245

138.17

262, 213

CH3CH2CH2CH2CHO CH3CH2CH2CH2CH3 H2N(CH2)5NH2 CH3CH2CH2CH(OH)CH2OH HO(CH2)5OH CH3CH2C("O)C("O)CH3 CH3COCH2COCH3 CH3CH2CH2CH2CN CH3(CH2)4SO3⫺ Na⫹

86.13 72.15 102.18 104.15 104.15 100.11 100.11 83.13 174.19

1, 676 1, 130 4, 266 12, 548 1, 481 1, 776 1, 777 2, 301 43, 23

0.809520 4 0.626220 4 0.87325 4 0.971 0.994120 0.957 0.972125 0.803515 4

CH3(CH2)4SH CH3(CH2)3CO2H CH3(CH2)4OH CH3CH2CH2CH(OH)CH3 CH3CH2CH(OH)CH2CH3 CH3CH2CH2COCH3 CH3CH2COCH2CH3 C6H5CO(CH2)3CH3 CH3(CH2)3COCl [-CH2CH2O-]5

104.22 102.13 88.15 88.15 88.15 86.13 86.13 162.23 120.58 220.27

1, 384 2, 299 1, 383 1, 384 1, 385 1, 676 1, 679 7, 327 2, 301

CH3(OCH2CH3)4OCH3

222.28

CH3CH2CH2CH"CH2 CH3CH2CH"CHCH3 CH3CH2CH"CHCH3 CH3CH2CH"CHCN CH3CH"CHCH2CN

70.14 70.14 70.14 81.12 81.12

⫺18 ⫺52 ⫺23.1 ⫺92 ⬎300

53

s aq, alc; sl s eth 17 aq; misc alc, eth i aq; s alc, eth 4 aq

INTERACTIVE

p48 p49 p50 p51 p52

[(CH3)2NCH2CH2]2NCH3

Formula weight

ROTATED

p47

N,N,N⬘,N⬘,N⬙-Pentamethyldiethylenetriamine 1,5-Pentamethylenetetrazole Pentanal Pentane 1,5-Pentanediamine 1,2-Pentanediol 1,5-Pentanediol 2,3-Pentanedione 2,4-Pentanedione Pentanenitrile 1-Pentanesulfonic acid, sodium salt 1-Pentanethiol Pentanoic acid 1-Pentanol 2-Pentanol 3-Pentanol 2-Pentanone 3-Pentanone Pentanophenone Pentanoyl chloride 1,4,7,10,13-Pentaoxacyclopentadecane 2,5,8,11,14-Pentaoxapentadecane 1-Pentene cis-2-Pentene trans-2-Pentene cis-2-Pentenenitrile trans-3-Pentenenitrile

Formula

LEFT

p37 p38 p39 p40 p41 p42 p43 p44 p45 p46

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

p60 p61

Pentyl acetate Pentylamine Pentylbenzene 2-Pentylcinnamaldehyde 4-tert-Pentylphenol 1-Pentyne Perfluoro-1-octanesulfonyl fluoride Peroxyacetic acid Petroleum ether

p62 p63

Phenanthrene 1,10-Phenanthroline

p64

Phenethylisobutyrate

p57 p58 p59

CH3(CH2)4O2CCH3 CH3(CH2)4NH2 CH3(CH2)4C6H5 C6H5CH"C[(CH2)4CH3]CHO

130.19 87.16 148.25 202.30

2, 131 4, 175 5, 434 72, 310

0.875320 0.754420 0.859420 4 0.970

1.402020 1.44820 1.488520 1.557120

CH3CH2C(CH3)2C6H4OH CH3CH2CH2C#CH CF3(CF2)7SO2F

164.25 68.11 502.12

6, 548 1, 250 24, 996

0.96220 4 0.690120 4 1.824

1.385220 1.301020

1.22615 4 0.640

1.387620 1.363020

178.23 180.21

2, 169 Merck: 12, 7329 5, 667 23, 227

192.26

62, 451

0.988

CH3C("O)CO2H Principally pentanes and hexanes

(CH3)2CHCO2CH2CH2C6H5

1.293

1.063

1.488020

tert-Pentylamine, d682 Pentyl bromide, b387 Pentyl chloride, c204a Pentyl cyanide, h61 Pentyl mercaptan, p37 Peracetic acid, p60 Perdeuterocyclohexane, c348 Perfluoropropane, h44 Perylene, d65 Phenacetin, e51 Phenacyl bromide, b251

149.2 104 202.2 290

16 ⫺1 65 ⬎110

93 ⫺106

262 40.2 154–155

⫺34 none

⫺0.2

110 35–60

41 ⫺49

100 114–117

340

250

0.17 aq; misc alc, eth v s aq; misc eth; s alc s alc, misc bz, eth

s alc, eth v s alc; misc eth

v s aq, alc, eth misc bz, chl, eth, CCl4; s glacial HOAc 1.6 alc; 50 bz; 30 eth 0.3 aq; 1.4 bz; s alc, acet

108

Phenacyl chloride, c31 Phenazone, a299 1,2,4-Phenenyl triacetate, t193 Phenethyl acetate, p111 Phenethyl alcohol, p110 sec-Phenethyl alcohol, m149 Phenethylamine, p112 Phenethyl bromide, b334 Phenethyl chloride, c128 Phenetole, e36

RIGHT

Pentamethylethyl alcohol, t362 1,5-Pentanedicarboxylic acid, h7 Pentanedinitrile, g17 Pentanedioic acid, g14 3,6,9,12,15-Pentaoxaheptadecane, t53 2,5,8,11,14-Pentaoxapentadecane, b212 Pentetic acid, d363 Pentyl alcohol, p39 sec-Pentyl alcohol, p40 tert-Pentyl alcohol, m162 sec-Pentylamine, a246

76.05

⫺70.8 ⫺55 ⫺78.3

DEAN 37261 (McGHP)

p53 p54 p55 p56

ROTATED

p27

p62

p63

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

1.294

Phenoxyacetyl chloride 4-Phenoxyaniline 2-Phenoxybutyric acid 2-Phenoxyethanol 1-Phenoxy-2-propanol 2-Phenoxypropionic acid 3-Phenoxypropyl bromide 3-Phenoxytoluene Phenylacetaldehyde Phenylacetaldehyde dimethyl acetal Phenylacetaldehyde ethylene acetal Phenyl acetate Phenylacetic acid Phenylacetonitrile Phenylacetyl chloride Phenylacetylene Phenylacetylurea

C6H5OCH2COCl C6H5OC6H4NH2 CH3CH2CH(OC6H5)CO2H C6H5OCH2CH2OH C6H5OCH2CH(OH)CH3 CH3CH(OC6H5)CO2H

170.60 185.23 180.20 138.17 152.19 166.18

6, 162 13, 438 6, 163 6, 146 61, 85 6, 163

1.235

C6H5O(CH2)3Br

215.10

6, 142

1.365

1.546020

C6H5OC6H4CH3 C6H5CH2CHO C6H5CH2CH(OCH3)2

184.24 120.15 166.22

6, 377 7, 292 7, 293

1.051 1.02725 25 1.004

1.572720 1.529020 1.493020

164.21

194, 220

1.100

1.522020

C6H5O2CCH3 C6H5CH2CO2H C6H5CH2CN C6H5CH2COCl C6H5C#CH C6H5CH2CONHCONH2

136.15 136.15 117.15 154.60 102.14 178.19

1.073 1.09177 4 1.0214 1.169 0.9300

1.503020

(⫾)-3-Phenylalanine Phenyl 4-aminosalicylate 4-Phenylazoaniline

C6H5CH2CH(NH2)CO2H H2NC6H3-2-(OH)CO2C6H5

165.19 229.24

C6H5N"NC6H4NH2

197.24

6, 152 9, 431 9, 441 9, 436 5, 511 Merck: 12, 7343 14, 495 Merck; 12, 7426 161, 310

1.10222 4 1.06325 4

41

182

261–263 185.1 98–100

371 285 sl dec

84 79–83 14 13–18 116–119

225–226 18914mm 258 245.2 240 265

1.534020

1.537020 1.52320

1.523320 1.532520 1.547020

33–34

76.5 ⫺23.8 ⫺44.9 212–216

79

108

⬎110 135

Solubility in 100 parts solvent 6.7 aq; 8.2 bz; v s alc, chl, eth, alk 8.2 alc; 1 eth v s bz; s eth; sl s alc 1.3 aq; v s alc, bz, HOAc, CS2, eth dec aq, alc; s eth s hot aq; v s alc, eth sl s aq s aq; v s alc, eth s alc; sl s aq

13414mm

96

271–273 195 221

⬎110 86 83

12012mm

107

196 265.5 233.5 9512mm 142.4

76

271–273 153 123–126

Flash point,⬚C

101 102 31

sl s aq; s alc, eth

misc alc, eth, chl s hot aq, alc, eth i aq; misc alc, eth dec aq, alc misc alc, eth sl s alc, bz, chl, eth 1.4 aq 0.7 mg aq

⬎360

v s alc, bz, chl, eth

INTERACTIVE

C6H5OCH2CO2H

Boiling point,⬚C

ROTATED

1.299

C6H5OH

Melting point,⬚C

LEFT

p88

1.541841

18, 143 27, 63 6, 161

p69 p70 p71 p72 p73 p74

p86 p87

Refractive index

318.33 199.28 152.15

Phenolphthalein Phenothiazine Phenoxyacetic acid

p80 p81 p82 p83 p84 p85

Density, g/mL 1.057641 4

p66 p67 p68

p79

Beilstein reference 6, 110

Phenol

p76 p77 p78

Formula weight 94.11

p65

p75

Formula

p90 p91 p92 p93 p94 p95 p96 p97 p98 p99 p100

Phenylazoformic acid 2-phenylhydrazide 4-Phenylazophenol 2-Phenylbenzimidazole Phenyl benzoate N-Phenylbenzylamine trans-4-Phenyl-3buten-2-one 2-Phenyl-3-butyn-2-ol 3-Phenylbutyraldehyde 2-Phenylbutyric acid 2-Phenylbutyronitrile Phenyl chloroformate Phenyl dichlorophosphate

C6H5N"NCONHNHC6H5

240.27

16, 24

C6H5N"NC6H4OH C6H5CO2C6H5 C6H5CH2NHC6H5 C6H5CH"CHCOCH3

198.23 194.24 198.22 183.25 146.19

16, 96 23, 230 9, 116 12, 1023 7, 364

1.235 1.061 1.009745 4

1.583645

CH3C(OH)(C6H5)C#CH CH3CH(C6H5)CH2CHO CH3CH2CH(C6H5)CO2H CH3CH2CH(C6H5)CN C6H5O2CCl C6H5OP(O)Cl2

146.19 148.21 164.20 145.21 156.57 210.98

62, 559 71, 168 92, 356 9, 541 6, 159 6, 179

0.997 1.055 0.974 1.248 1.412

1.517920 1.516020 1.508620 1.510720 1.523020

1.295

4-Phenoxybutyl bromide, b281 Phenylacetaldehyde dimethyl acetal, d516 N-Phenylacetamide, a18 2-Phenylacetoacetonitrile, a51 Phenylacetone, p147 ␣-Phenylacetophenone, d26 ␤-Phenylacrylic acid, c279 ␥-Phenylallyl alcohol, c282 Phenylamine, a293 ␤(Phenylamino)phenol, h115

156–159 dec 150–152 293–296 69–72 35–38 41.5 47–49 42–44

23020mm 298–299 306–307 260–262

⬎110 65

217–218 9416mm 270–2 11415mm 719mm 241–243

96 96 ⬎110 105 75 ⬎110

v s alc, eth s abs alc; sl s bz, chl v s hot alc; sl s eth s alc, chl, eth v s alc, bz, chl, eth 0.8 aq; s alc, bz, acet s bz, eth

DEAN 37261 (McGHP)

p89

1-Phenylbutane, b521 2-Phenylbutane, b522 1-Phenyl-1,3-butanedione, b63 4-Phenyl-2-butanone, b77a Phenyl cellosolve, p72 Phenyl chloride, c47 Phenylcyclohexane, c376 2-Phenylcinchoninic acid, p153 ␣-Phenyl-o-cresol, h116

N-Phenylaniline, d760 o-Phenylanisole, m63 Phenylarsonic acid, b12 Phenylazoformic acid 2-phenylhydrazide, d746 N-Phenylbenzamide, b5 Phenylbenzene, b138 ␣-Phenylbenzenemethanamine, a159 Phenylbenzoic acid, b139 Phenylboric acid, b13 Phenyl bromide, b262

RIGHT ROTATED

p66

p67

p79

p91

INTERACTIVE

N-Phenyldiethanolamine 4-Phenyl-1,3-dioxane 2-Phenyl-1,3-dioxolane 1,2-Phenylenediamine 1,3-Phenylenediamine 1,4-Phenylenediamine 1,4-Phenylene diisocyanate 1-Phenyl-1,2ethanediol 1-Phenylethanol 2-Phenylethanol 2-Phenylethyl acetate 2-Phenylethylamine 1-Phenylethyl propionate (⫾)-2-Phenylglycine 1-Phenylheptane 1-Phenylhexane Phenylhydrazine Phenyl 1-hydroxy-2naphthoate Phenyl 3-hydroxy-2naphthoate 2-Phenylimidazole 2-Phenyl-2-imidazoline 2-Phenyl-1,3indandione 2-Phenylindole Phenyl isocyanate Phenyl isothiocyanate N-Phenylmaleimide Phenylmalonic acid

p102 p103 p104 p105 p106 p107 p108

1.296

p109 p110 p111 p112 p113 p114 p115 p116 p117 p118 p119 p120 p121 p122 p123 p124 p125 p126 p127

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

C6H5N(CH2CH2OH)2

181.24

12, 183

1.12060 20

191, 616

1.111 1.106

C6H4-1,2-(NH2)2 C6H4-1,3-(NH2)2 C6H4-1,4-(NH2)2 C6H4-1,4-(NCO)2

164.21 150.18 108.14 108.14 108.14 160.13

13, 13, 13, 13,

C6H5CH(OH)CH2OH

138.17

6, 907

CH3CH(OH)(C6H5) C6H5CH2CH2OH CH3CO2CH2CH2C6H5 C6H5CH2CH2NH2 C2H5CO2CH(CH3)C6H5

122.17 122.17 164.20 212.18 178.23

6, 475 6, 478 9, 510 12, 1096 53, 1680

1.013020 1.02325 25 0.984 0.964025 4 1.007

1.527020 1.531720 1.498520 1.529025 1.489520

C6H5CH(NH2)CO2H C6H5(CH2)6CH3 C6H5(CH2)5CH3 C6H5NHNH2 HOC10H6CO2C6H5

151.17 176.30 162.28 108.14 264.28

14, 460 5, 451 52, 337 152, 44 10, 332

0.860 0.861 1.097820 4

1.485020 1.486020 1.608020

C10H6(OH)CO2C6H5

264.28

10, 335

129–132

144.18 146.19 222.28

23, 182 23, 154 7, 808

144–147 94–99 148–150

193.25 119.12 135.19 173.17 180.16

20, 467 12, 437 12, 453 21, 400

C6H5NCO C6H5NCS C6H5CH(CO2H)2

6 33 61 105

Flash point,⬚C

56–80

350 sl dec

103 63.5 146 97–98

250–251 800.3mm 257 285 267 260

66–68

272–274

20 ⫺27

204 221 238–239 197.5 925mm

85 102 101 90 94

233 226 243

95 83 88

1.530020 1.526020

1.13915

Boiling point,⬚C

⬍0

5 aq; v s alc; 29 eth; 25 bz ⬎110 98

156 ⬎110

subl 255

1.095620 4 1.128825 4

1.535020 1.649720

⫺61 19.5 94–96

188–190 ⫺30 ⫺21 85–87 153 dec

Solubility in 100 parts solvent

v s alc, chl, eth; sl s aq s aq, alc, acet, chl 1 aq; s alc, chl, eth

v s aq, alc, bz, eth, chl, HOAc 2.3 aq 2 aq; misc alc, eth 2 aq; misc alc, eth 80 aq15; s alc; i eth

s org solvents, alk misc eth misc alc, bz, chl, eth

261160mm

25010mm 162–163 221 16312mm

55 87

dec aq, alc; s eth i aq; s alc, eth s alc, chl, eth

INTERACTIVE

p101

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

p129 p130 p131 p132 p133

Phenylmercury(II) acetate Phenylmercury(II) chloride Phenylmercury(II) hydroxide N-Phenylmorpholine N-Phenyl-1naphthylamine N-Phenyl-2naphthylamine

C6H5HgO2CCH3

336.74

C6H5HgCl

313.15

C6H5HgOH

294.70

Merck: 12, 7453 Merck: 12, 7454 16, 952

C10H7NHC6H5

163.22 219.29

27, 6 12, 1224

C10H7NHC6H5

219.29

12, 1275

150–152

0.17 aq; s alc, bz, acet

250–252

s bz, eth, pyr

190 dec 1.058270

51–54 60–62

268 22615mm

107–109

395

1-Phenylethanone, a31 Phenylethene, s11 N-Phenylformamide, f35 Phenylglyoxylic acid, b69 Phenylglyoxylonitrile, b67

Phenylethane, e74 Phenylethanenitrile, p82 1-Phenylethanol, m149 Phenylethanolamine, a257 N-Phenylethanolamine, a295

⬎110

1.0 aq; v s hot alc s alc, bz, chl, eth

DEAN 37261 (McGHP)

p128

2,2⬘-(Phenylimino)diethanol, p101 p-(2-Phenylisopropyl)phenol, m316a Phenyl mercaptan, t156 Phenylmethanol, b78

1.297 p103

p120

p121

p122

RIGHT

p102

ROTATED

p123

p126

p131

INTERACTIVE

Name

p134 p135 p136 p137

2-Phenyl-2-oxazoline 2-Phenylphenol 4-Phenylphenol N-Phenyl-1,4phenylenediamine Phenylphosphinic acid Phenylphosphonic acid Phenylphosphonic dichloride N-Phenylpiperazine 1-Phenylpiperidine 2-Phenyl-1,2propanediol 3-Phenyl-1propanethiol 1-Phenyl-1-propanol 3-Phenyl-1-propanol 1-Phenyl-2-propanone 2-Phenylpropionaldehyde 3-Phenylpropionaldehyde 3-Phenylpropionic acid

p138 p139 p140 p141 p142 p143

1.298

p144 p145 p146 p147 p148 p149 p150

p155

Phenylsuccinic acid

p152 p153

Beilstein reference

C6H5C6H4OH C6H5C6H4OH C6H5NHC6H4NH2

147.18 170.21 170.21 184.24

27, 47 62, 623 6, 674 13, 76

C6H5PH(O)OH C6H5P(O)(OH)2 C6H5P(O)Cl2

142.09 158.09 194.99

16, 791 16, 803 16, 804

CH3C(C6H5)(OH)CH2OH

162.24 161.25 152.19

C6H5CH2CH2CH2SH

Density, g/mL

Refractive index

1.118 1.213

1.567020

1.375

1.560020

233, 49 20, 22 6, 930

1.062120 4 1.001

1.587520 1.562020

152.26

61, 253

1.010

1.549420

C6H5CH(OH)CH2CH3 C6H5CH2CH2CH2OH C6H5CH2COCH3 CH3CH(C6H5)CHO

136.19 136.19 134.18 134.18

6, 502 6, 503 72, 233 7, 305

0.991525 4 1.008 1.015720 4 1.00920 4

1.520020 1.525720 1.516020 1.517520

C6H5CH2CH2CHO

134.18

7, 304

1.019

1.523020

C6H5CH2CH2CO2H

150.18

9, 508

1.047100 4

162.19

24, 2

C6H5C5H4N

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

750.3mm 282 321

123 165

85–87 163–166 3

258

⬎110

3–4 44–45

286 257–258 16226mm

⬎110 106 ⬎110

10910mm

90

219 235 10013mm 202–205

90 109 84 76

9812mm

95

280

⬎110

268–270

⬎110

44–46

17312mm

⬎110

167–169

⫺H2O, ⬎168

12 57–59 165–167 73–75

⫺18 27

47–49 121–123

155.20 249.27

20, 424 22, 103

1.086

C6H5(OH)CO2C6H5

214.22

10, 76

1.25

HO2CCH2CH(C6H5)CO2H

194.19

9, 865

20

1.6332

214–215

Solubility in 100 parts solvent

s alc, chl, eth, alk s alc, chl, eth, alk

i aq; misc alc

misc alc, bz s aq; misc alc, eth v s alc, eth; misc bz i aq; s alc

0.6 aq; s bz, alc, chl, eth, HOAc, PE 10 hot aq; s hot alc, alk, acid s alc, eth 0.8 alc; 1 eth; 0.3 chl 17 alc; 66 bz; s acet, chl, eth; 0.015 aq s hot aq, alc, eth

INTERACTIVE

p154

1-Phenyl-3pyrazolidinone 2-Phenylpyridine 2-Phenyl-4-quinolinecarboxylic acid Phenyl salicylate

Formula weight

ROTATED

p151

Formula

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

p158 p159 p160 p161 p162 p163 p164 p165

1.299

p166 p167

(Phenylthio)acetic acid S-Phenyl thioisobutyrate 1-Phenyl-2-thiourea Phenyltrichlorosilane Phenyltriethoxysilane Phenyltrimethoxysilane Phenyltrimethylammonium bromide Phenyltrimethylammonium chloride Phenyltrimethylammonium iodide Phenyltrimethylammonium tribromide Phenyltrimethylsilane Phenylurea

C6H5SCH2CO2H (CH3)2CHC("O)SC6H5

168.21 152.22

6, 313 6,4, 1524

1.056

1.546020

64–66

C6H5NHC(S)NH2 C6H5SiCl3 C6H5Si(OC2H5)3 C6H5Si(OCH3)3

152.22 211.55 240.38 198.30

12, 388 16, 911 16, 911 164, 1556

1.3 1.32920 0.996 1.062

1.523020 1.460420 1.468020

[C6H5N(CH3)3]⫹ Br⫺

216.13

12, 158

215 dec

v s aq; s hot alc

[C6H5N(CH3)3]⫹ Cl⫺

171.67

12, 158

237 subl

s aq; v s alc; sl s eth

[C6H5N(CH3)3]⫹ I⫺

263.12

12, 159

227 subl

s aq, alc; sl s acet

[C6H5N(CH3)3]⫹ Br⫺3

375.95

12, 159

114–116

C6H5Si(CH3)3 C6H5NHCONH2

150.30 136.15

161, 525 12, 346

0.873 1.302

⬎110

201 11310mm 233

91 42 99

154

1.490720 145–147

3-Phenylpropyl mercaptan, p144 Phenyl sulfide, d770 Phenyl sulfone, d771 Phenylsulfonic acid, b23 Phenyl sulfoxide, d772 (Phenylthio)acetic acid, t157

0.25 aq; s alc, alk

168–170 238

44 s hot aq, hot alc, eth

Phenyl thiocarbamide, p158 ␣-Phenyl-o-toluic acid, b84 Phenyl m-tolyl ether, p76 Phloroglucinol, t318 Phorone, d613 Phthalaldehydic acid, f37

RIGHT

1-Phenylpentane, p55 2-Phenylpropane, i103 3-Phenyl-2-propenoic acid, e279 3-Phenyl-2-propen-1-ol, c282 3-Phenyl-2-propenoyl chloride, c280 3-Phenylpropyl alcohol, p146 Phenyl propyl ketone, b619

12910mm

DEAN 37261 (McGHP)

p156 p157

ROTATED

N

p134

p141

p142

p151

p153

INTERACTIVE

No.

Name

1.300

p169 p170 p171 p172 p173

Phthalic anhydride Phthalide Phthalimide 1,2-Phthaloyl dichloride Phthalylsulfathioazole

p174

Picric acid

p175 p176 p177 p178 p179

(⫹)-␣-Pinene (⫺)-␤-Pinene ␣-Pinene oxide Piperazine 1,4-Piperazinebis(ethanesulfonic acid) Piperidine 1-Piperidinecarbonitrile N-Piperidineethanol 2-Piperidineethanol 1-Piperidinepropionic acid Piperidinepropionitrile 2-(2-Piperidineethyl)pyridine L-Proline

p180 p181 p182 p183 p184 p185 p186 p187

Density, g/mL

C6H4-1,2-(CO2H)2

166.13

9, 791

1.59320 4

17, 469 17, 310 21, 458 9, 805

1.53 1.16499 4

C6H5-1,2-(COCl)2

148.12 134.13 147.13 203.02 403.44

Merck: 12, 7533 6, 265

2,4,6-(O2N)3C6H2OH

229.11

1.40920

1.76320 4

0.862220 4 0.951

1.452520 1.470520

⫺13

0.873225 25 1.01017

1.480420

0.933 0.985

1.469520 1.526020

85.15 110.16

20, 6 20, 56

129.20 129.20 157.21

20, 25 21, 2 203, 1049

Pimelic ketone, c366 Pinacolone, d572 Pinacolyl alcohol, d571

122–123 ⫺62 ⫺61

0.859120 4 0.859020 0.964

22, 2

230 rapid heating 131–134 72–74 234–236 15–16

1.465020 1.478020 1.469020 1.446113

5, 146 5, 154 5, 152 23, 4 Merck: 12, 7633

115.13

1.568420

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

295 290

151

280–282

⬎110

272–277

136.24 136.24 152.24 86.14 302.37

138.21 190.29

Refractive index

108–110 ⬎300

38–40 105–110

Solubility in 100 parts solvent 0.6 aq; ;10 alc; 0.5 eth; v sl s chl 0.6 aq(dec); s alc s alc v s alk; v sl s bz, PE dec by aq, alc; s eth s alk; sl s alc; i chl

explodes ⬎300 156 166 10350mm 145–146

35 38 65 109

106 10210mm

4 97

misc aq; s alc, bz, chl

199–202 234 1080.5mm

68 102

misc aq; s alc v s aq, alc, eth

11116mm 15017mm

102 ⬎110

228 dec

Pivalic acid, d679 Pivalic anhydride, d680 Pivaloyl chloride, d681

1.3 aq; 8.2 alc; 10 bz; 2.9 chl; 1.6 eth misc alc, eth

v s aq; 50 alc; i eth

INTERACTIVE

m-Phthalic acid, b17 p-Phthalic acid, b18 Phthalonitrile, d282

Beilstein reference

ROTATED

1,2-Phthalic acid

Formula weight

LEFT

p168

Formula

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

1.301

p169

p171

p178

Pivaloyloxymethyl chloride, c172 POPOP, b218 PPO, d779 Prehnitene, t97 Propadiene, a72 1-Propanal, p211

p173

p179

p180

p175

p181

p182

p176

p183

RIGHT

p177

p170

DEAN 37261 (McGHP)

Pipecolines, m381 thru m383 1-Piperazinoethanol, h129 1-Piperidinecarboxyaldehyde, f40 Piperonal, m250 Piperonyl butoxide, m252 cis-Piperylene, p16 Pivaldehyde, d677

Picolinaldehyde, p261 Picolines, m409 thru m411 Picolinic acids, p265, p267 Picolinonitrile, c328 Picolylamines, a218 thru a220 Picramide, t402 Pimelic acid, h7

ROTATED

p185

p186

p187

INTERACTIVE

p184

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

1.302

p188

Propane

CH3CH2CH3

44.10

1, 103

0.584⫺42

1.340⫺42

⫺188

⫺42.1

⫺104

p189 p190 p191

1,2-Propanediamine 1,3-Propanediamine 1,2-Propanediol

CH3CH(NH2)CH2NH2 H2NCH2CH2CH2NH2 CH3CH(OH)CH2OH

74.13 74.13 76.10

4, 257 4, 261 1, 472

0.87815 0.88425 4 1.036420 4

1.446020 1.457520 1.433120

⫺12 ⫺60

119–120 140 188

33 48 107

p192

1,3-Propanediol

HOCH2CH2CH2OH

76.10

1, 475

1.053820

1.439620

⫺27

214

79

p193

1,3-Propanediol bis(4-aminobenzoate) 1,2-Propanediol dibenzoate 1,3-Propanedithiol 1-Propanesulfonyl chloride 1,3-Propane sultone 1-Propanethiol 2-Propanethiol 1,2,3-Propanetriol tris(acetate) 1-Propanol 2-Propanol 2-Propenal Propene

CH2(CH2CO2CC6H4NH2)2

314.34

143, 1034

1.140

C6H5CO2CH2CH(CH3)O2CC6H5 HSCH2CH2CH2SH CH3CH2CH2SO2Cl

284.31

9, 129

1.160

1.545020

⫺3

23212mm

⬎110

108.23 142.60

1, 476 4, 8

1.077220 4 1.286415 4

1.540520 1.454220

⫺79

172.9 668mm

58 80

122.14 76.16 76.16 218.21

193, 4 1, 359 1, 367 2, 147

1.392 0.83625 4 0.80925 4 1.158020

1.438020 1.425520 1.430220

31–33 ⫺113 ⫺131 ⫺78

18030mm 67–68 52.6 259

⬎110 ⫺20 ⫺34 138

60.10 60.10 56.07 42.08

1, 350 1, 360 1, 725 1, 196

0.803720 0.785520 4 0.84120 4 ⫺48 0.610 4

1.384020 1.377220 1.401720 1.3567⫺40

⫺127 ⫺89.5 ⫺88 ⫺185.2

97.2 82.4 52.6 ⫺47.7

23 12 ⫺18 ⫺108

2-Propene-1-thiol trans-1,2,3-Propenetricarboxylic acid 1-Propen-2-yl acetate

H2C"CHCH2SH

74.15 174.11

1, 440 2, 849

0.92523 4

1.476520

67–68

21

97

18

p194 p195 p196

p205 p206

H2C"C(O2CCH3)CH3

100.12

190 dec 0.909

1.400020

misc alc, bz, eth, chl dec hot aq, hot alc

s alc, eth misc alc, eth; sl s aq 7.2 aq; misc alc, bz, chl, eth misc aq, alc, eth misc aq, alc, chl, eth 21 aq; s alc, eth vols in 100 vols solvent: 45 aq; 1200 alc; 500 acet misc alc, eth 50 aq25; 50 88% alc12; sl s eth

INTERACTIVE

p207

CH3CH2CH2OH (CH3)2CHOH H2C"CHCHO H2C"CHCH3

124–127

ROTATED

p201 p202 p203 p204

CH3CH2CH2SH CH3CH(SH)CH3 H3CCO2CH(CH2O2CCH3)3

volumes per 100 vols solvent: 6.5 aq; 790 alc; 926 eth; 1300 chl; 1450 bz misc aq, bz; s alc, eth misc alc, eth; s aq misc aq, acet, chl; s alc, eth misc aq, alc

LEFT

p197 p198 p199 p200

Solubility in 100 parts solvent

p209 p210

p211 p212 p213 p214 p215 p216 p217 p218 p219

1.303

p220 p221 p222 p223

4-(1-Propenyloxymethyl)-1,3-dioxolan-2-one 2-Propenylphenol ␤-Propiolactone

Propionaldehyde Propionamide Propionic acid Propionic anhydride Propionitrile Propionyl chloride Propiophenone 2-Propoxyethanol 2-(2-Propoxyethyl)pyridine 1-Propoxy-2-propanol Propoxytrimethylsilane Propyl acetate Propylamine

158.16

1.100

1.461020

134.18 72.06

61, 279 171, 130

1.044 1.146020 4

1.578020 1.413120

CH3CH2CHO CH3CH2CONH2 CH3CH2CO2H [CH3CH2C("O)]2O CH3CH2CN CH3CH2COCl C6H5COCH2CH3 CH3CH2CH2OCH2CH2OH C5H4NCH2CH2OCH2CH2CH3

58.08 73.10 74.09 130.14 55.08 92.53 134.18 104.15 165.24

1, 629 2, 243 2, 234 2, 242 2, 245 2, 243 72, 231 1, 468

0.807120 4 0.959780 4 0.993420 4 1.011020 0.781820 4 1.06520 4 1.010520 4 0.913 0.954

1.363620 1.4160110 1.380920 1.403720 1.365820 1.405120 1.525820 1.413020 1.488020

C5H4NCH2CH2OCH2CH(OH)CH3 CH3CH2CH2OSi(CH3)3 CH3CH2CH2O2CCH3 CH3CH2CH2NH2

118.18 132.28 102.13 59.11

12, 536 4,4, 3994 2, 129 4, 136

0.885 0.76820 4 0.8878 0.717320

1.411020 1.384020 1.384420 1.387220

CH3CH"CHC6H4OH

⬎110

⫺33.4

230–231 162

90 70

⫺81 79 ⫺20.5 ⫺45 ⫺92.8 ⫺94 21 ⫺75

48 222.2 141.1 170 97.2 80 218.0 150–153

⫺30

⫺93 ⫺83

140–160 100735mm 101.6 42.2

52 63 2 11 87 48 95 48 ⫺2 13 ⫺37

2-Propenyl acetate, a74 2-Propenylamine, a74 Propenylanisole, m107 N-2-Propenyl-2-propen-1-amine, d30 (2-Propenyl)thiourea, a97 Propiolic acid, p248 Propyl alcohol, p201

37 aq(hyd); misc alc (reacts); bz, eth, acet 30 aq; misc alc, eth v s aq, alc, chl, eth misc aq; s alc, chl, eth dec aq; s alc, chl, eth 10 aq; misc alc, eth dec by aq, alc misc bz, eth, abs alc

2.3 aq; misc alc, eth misc aq, alc, eth

RIGHT

Propargyl alcohol, p249 Propargyl chloride, c241 Propenamide, a61 2-Propen-1-amine, a76 2-Propenenitrile, a63 3-Propenoic acid, a62 2-Propen-1-ol, a75

1,3-Propanedicarboxylic acid, g14 Propanedioic acid, m3 1,2-Propanediol cyclic carbonate, p230 Propanenitrile, p215 1,2,3-Propanetriol, g19 Propanoic acid, p213 2-Propanone, a26

251–252

DEAN 37261 (McGHP)

p208

ROTATED

p197

p206

p208

p210

INTERACTIVE

No. p224

Name

1.304

Melting point,⬚C

0.900

1.441520

CH3CH2CH2C6H5 C6H5CO2CH2CH2CH3 CH3CH2CH2CO2CH2CH2CH3 ClCO2CH2CH2CH3 CH3CH2CH2C6H11

5, 390 9, 112 2, 271 3, 11 52, 23 193, 1564 20, 3

0.862120 4 1.03220 0.87915 4 1.090 0.792920 4 1.204120 0.801725

1.491220 1.501020 1.400020 1.403420 1.437020 1.421020 1.408425

⫺99.2 ⫺51.6 ⫺95

CH3CH 9 CH2

120.20 164.20 130.19 122.55 126.24 102.09 57.09

1,2-Propylene oxide

NH CH3CH 9 CH2

58.08

17, 6

0.828720

1.366020

⫺112

Propylene sulfide

O CH3CH 9 CH2

Propyl formate Propyl 4-hydroxybenzoate Propyl isocyanate Propyl lactate Propyl nitrate

Flash point,⬚C

182746mm

78

159.2 230 143 105–106 156.7 242 66.0

47 98 38 28 35 135 ⫺15

s alc, eth i aq; s alc, eth sl s aq; misc alc, eth misc bz, chl, eth s bz, eth v s aq, alc, bz, eth misc aq, alc, PE

34

⫺35 (CC)

41 aq; misc alc, eth

72–75

10

80.9

⫺3

83–84 8640mm 110.1

0

74.15

172, 15

0.946

1.476020

S CH3CH2CH2O2CH HOC6H4CO2CH2CH2CH3

88.10 180.20

2, 21 10, 160

0.905820

1.377920

CH3CH2CH2NCO CH3CH(OH)CO2CH2CH2CH3 CH3CH2CH2ONO2

85.11 132.16 105.09

41, 366 3, 265 1, 355

0.908 0.99620 1.053820 4

1.394020 1.416725 1.397620

(CH3CH2CH2)2CHCO2H CH3CH2CH2C6H4OH CH3CH2CH2P(O)Cl2

144.21 136.19 160.97

2, 350 6, 499 4, 596

0.921 1.01520 1.290

1.425020 1.527920 1.464320

220 224–226 9050mm

23 (may explode on heating) 111 93 ⬎110

CH3CH2CH2SiCl3

177.53 141.22 116.16

4, 630

1.185120 4 0.936 0.88320

1.42920 1.460020 1.393520

123–124 561mm 122.5

2 75 19

CH3CH2CO2CH2CH2CH3

2, 240

⫺92.9 95–98

⫺100

⫺76

Solubility in 100 parts solvent

2 aq; misc alc, eth 0.05 aq; v s alc, eth

s aq, alc, eth s alc, eth

s alc, eth

0.5 aq; 103 alc; 83 eth

INTERACTIVE

2-Propylpentanoic acid 2-Propylphenol Propylphosphonic dichloride Propyltrichlorosilane 1-Propyl-4-piperidone Propyl propionate

⫺94.9 ⫺48.8

Boiling point,⬚C

ROTATED

p242 p243 p244

Refractive index

LEFT

p239 p240 p241

Density, g/mL

4, 282

p232

p236 p237 p238

Beilstein reference

103.17

p225 p226 p227 p228 p229 p230 p231

p234 p235

Formula weight

C3H7NHCH2CH2OH

2-(Propylamino)ethanol Propylbenzene Propyl benzoate Propyl butyrate Propyl chloroformate Propylcyclohexane Propylene carbonate Propyleneimine

p233

Formula

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

(HO)3C6H2CO2CH2CH2CH3

212.20

CH3C#CH C6H5SO3CH2C#CH

40.06 196.23

Merck: 12, 8044 1, 246 113, 37

HC#CCO2H HC#CH2OH

70.05 56.06 152.24 80.09 105.10 124.10

2, 477 1, 454 7, 87 23, 91 253, 777 25, 125

p254 p255 p256

Propyl 3,4,5-trihydroxybenzoate Propyne 2-Propynyl benzenesulfonate 2-Propynoic acid 2-Propyn-1-ol (⫹)-Pulegone Pyrazine Pyrazinecarbonitrile Pyrazinecarboxylic acid Pyrazole Pyrene Pyridazine

68.08 202.26 80.09

23, 39 5, 693 23, 89

p257 p258 p259

Pyridine Pyridine-d5 2-Pyridinealdoxime

C5H5N C5D5N (C5H4N)-2-CH"NOH

79.10 84.14 122.13

20, 181 203, 2305 211, 288

p246 p247 p248 p249 p250 p251 p252 p253

150 0.691⫺420 1.243

1.3725⫺20 1.525020

⫺102.8 ⫺30

⫺23.2 1422mm

100

1.13820 4 0.947820 0.934615 4 1.03161 4 1.174

1.432020 1.432020 1.487020 1.495361 1.534020

9 ⫺51.8

102200mm 114 224 115 876mm

58 36 85 55 96

55

v s alc; 3000 mL eth

s aq, alc, eth misc aq, alc, bz, chl misc alc, chl, eth v s aq, alc, eth

225 dec 1.4203 1.27123 1.103525 4

1.523023

0.982725 4 1.050

1.506725 1.509220

68 151 ⫺8

187 404 208

85

⫺41.6

115.2 114.4

20 20

sl s hot aq; 0.008 abs alc; i bz, chl, eth s aq, alc, bz, eth s org solvents misc aq, bz; v s alc, eth misc aq, alc, eth

1.305

110–112

Propylenediamine, p189 Propylene glycol, p191 Propylene glycol dimethyl ether, d518 Propylene glycol monomethyl ether, m105 Propylene glycol monophenyl ether, p73 Propylene oxide, e15 Propyl gallate, p245

Propyl iodide, i48 Propyl mercaptan, p198 6-Propyl-2-thiouracil, h140 Pseudocumene, t358 Pyrene, b52 3,6-Pyridazinediol, d447

RIGHT

Propyl bromide, b400 Propyl butanoate, p227 Propyl cyanide, b468a Propyl chloride, c225 Propylene, p204 sec-Propylene chlorohydrin, c230 Propylene dibromide, d120

0.35 aq; 1 alc; 83 eth

DEAN 37261 (McGHP)

p245

ROTATED

p230

p243

p250

p251

p252

p253

p254

p255

p256

INTERACTIVE

4-Pyridinealdoxime 2-Pyridinecarboxaldehyde 3-Pyridinecarboxaldehyde 4-Pyridinecarboxaldehyde 3-Pyridinecarboxamide 2-Pyridinecarboxylic acid 3-Pyridinecarboxylic acid 4-Pyridinecarboxylic acid 2,3-Pyridinedicarboxylic acid 2,5-Pyridinedicarboxylic acid 2,6-Pyridinedicarboxylic acid Pyridine-N-oxide Pyridinium p-toluenesulfonate 2-Pyridylcarbinol 3-Pyridylcarbinol 3-(3-Pyridyl)-1propanol 3-(4-Pyridyl)-1propanol Pyrimidine 2,4(1H,3H)Pyrimidinedione Pyrrole Pyrrolidine

p262 p263 p264 p265 p266 p267

1.306

p268 p269 p270 p271 p272 p273 p274 p275 p276 p277 p278 p279 p280

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

(C5H4N)-4-CH"NOH (C5H4N)-2-CHO

122.13 107.11

211, 287

1.126

1.537020

181

54

(C5H4N)-3-CHO

107.11

211, 288

1.135

1.549320

9715mm

60

(C5H4N)-4-CHO

107.11

21, 287

1.122

1.544020

7812mm

54

(C5H4N)-3-CONH2 (C5H4N)-2-CO2H

122.13 123.11

22, 40 22, 33

1.400

1.466

(C5H4N)-3-CO2H

123.11

22, 38

1.473

(C5H4N)-4-CO2H

123.11

(C5H4N)-2,3-(CO2H)2

Solubility in 100 parts solvent

130–133

s aq, eth

130–133 134–136

sublimes

100 aq; 66 alc s aq, alc, bz; v s HOAc 1.4 aq; s alk; v s hot aq, hot alc 0.52 aq; i alc, bz, eth

236.6

sublimes

22, 45

319

26015mm

167.12

22, 150

0.56 aq; s alk

(C5H4N)-2,5-(CO2H)2

167.12

22, 153

188–190 dec 256 dec

(C5H4N)-2,6-(CO2H)2

167.12

22, 154

sl s aq; v sl s alc

C5H5NO C5H5NH⫹ ⫺O3SC6H4CH3

95.10 251.31

202, 131 202, 129

248–250 dec 61–65 117–119

(C5H4N)-2-CH2OH (C5H4N)-3-CH2OH (C5H4N)-3-CH2CH2CH2OH

109.13 109.13 137.18

211, 203 21, 50 213, 549

1.131 1.124 1.063

(C5H4N)-4-CH2CH2CH2OH

137.18

214, 550

1.061

80.09 112.09

23, 89 24, 312

1.016

67.09 71.12

20, 159 20, 4

0.969120 4 0.858620

s hot acid

270

11316mm 15428mm 1333mm

⬎110 ⬎110 ⬎110

35–39

289

⬎110

1.504020

22 335

124

31

misc aq; s alc, eth 0.3 aq; s alk

1.508520 1.443120

⫺23.4 ⫺58

130 86.5

39 3

4.5 aq; v s alc, eth misc aq; s alc, chl, eth

1.542020 1.544520 1.530020

v s aq, alc, eth v s aq, eth

INTERACTIVE

p260 p261

Formula

ROTATED

Name

LEFT

No.

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

p282

p283 p284 p285 p286

1-Pyrrolidinebutyronitrile 1-Pyrrolidinecarbodithioic acid, ammonium salt 1-Pyrrolidinecarbonitrile 1-Pyrrolidino-1cyclohexene 2-Pyrrolidinone

138.21

3-(N-Pyrrolidino)1,2-propanediol

145.20

0.926

1.460520

164.29

153–155

0.954

1.469020

771.8mm

107

151.25

0.940

1.522520

11515mm

39

1.11625 4

1.480625

25

251

129

46–48

15830mm

⬎110

21, 236 201, 4

1.307

Pyrocatechol, d428 Pyrogallol, t317 Pyromellitic acid, b27 Pyromellitic dianhydride, b28 Pyromucic aldehyde, f44 Pyrrolidinedithiocarbamate, p282

p278

p279

p280

misc aq, alc, bz, chl, eth, EtOAc

1-Pyrrolidineethanol, h133 4-(N-Pyrrolidino)butyronitrile, p281 Pyruvic acid, o65 Pyruvic aldehyde, o64 Pyruvic aldehyde dimethyl acetal, d520

p281

p282

RIGHT

p277

99

96.13

85.11

2,3-Pyridinediol, d448 2-Pyridineethanol, h132 3-Pyridinol N-oxide, h183 Pyridinols, h179 thru h181 2(1H)-Pyridone, h179 2-(2-Pyridyl)pyridine, d790

11518mm

DEAN 37261 (McGHP)

p281

ROTATED

p283

p284

p285

p286

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No. q1 q2 q3 q4 q5 r1 r2

1.308

r3

Name Quinhydrone Quinine Quinoline Quinoxaline 2-Quinoxalinol D-Raffinose pentahydrate Resorcinol

r7

r4 r5

Formula weight

Beilstein reference

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

7, 617 23, 511 20, 339 23, 176 24, 147 31, 462

1.40120 4

C6H4-1,3-(OH)2

110.11

6, 796

1.272

C6H4-1,3-(O2CCH3)2

194.19

6, 816

1.178

1.503020

14612mm

⬎110

CH3CO2C6H4-3-(OH)

152.15

6, 816

1.223

1.537020

ca 283

⬎110

C6H5CO2C6H4-3-(OH)

214.20

171–173 173–175 ⫺15 29–32 271–272 80–82

237 220–223 dec 118

14 aq; 10 MeOH

110–112

280

111 aq; 111 alc; v s eth

101 98

s hot aq, alc, eth 125 alc; 1.2 bz; 83 chl 0.6 aq; misc alc, eth v s aq, alc, bz, eth

i aq; misc alc, bz, chl, acet; s alk OH’s

133.19

27, 242

r8

Riboflavin

376.37

Merck: 12, 8367

r9 s1

D-Ribose

150.13 183.19

1, 859 27, 168

0.868

0.828

210–211 dec 167–170 may explode on rapid heating dec 278– 282 88–92 228–230

v s aq, alc v s hot aq, alc, eth

v s alk(dec); i acet, bz, eth; sl s pentyl acetate, cyclohexanol s aq; sl s alc 0.34 aq; 3 alc; 8 acet

ROTATED

Rhodanine

INTERACTIVE

p-Quinone, b58

1.09520 4 1.33448 4

1.625 1.627320 1.623148

Solubility in 100 parts solvent

133–135 19, 345

Quinaldine, m420

Refractive index

218.20 324.44 129.16 130.15 146.15 594.52

479.02

Saccharin

Density, g/mL

LEFT

r6

Resorcinol 1,3diacetate Resorcinol monoacetate Resorcinol monobenzoate Rhodamine B

Formula

DEAN 37261 (McGHP)

1.309

RIGHT

ROTATED

s1

INTERACTIVE

r9

r8 r7 r6 r1

q5 q4 q3 q2 q1

No. s2 s3 s4 s5

Name Safrole Semicarbazide hydrochloride L-Serine D-Sorbitol

Formula

H2NNHCONH2 · HCl HOCH2CH(NH2)CO2H

Formula weight

Beilstein reference

Density, g/mL

Refractive index

1.09520

1.537020

1.310

Melting point,⬚C

Boiling point,⬚C 232–234

350

218

55 aq; v sl s alc s bz, chl, eth, PE

200

v s eth, acet, PE v s bz, eth 0.66 alc; 20 chl; 0.55 bz; 0.15 mg aq s alc, acet, eth, CS2

162.19 111.53

19, 39 3, 98

105.09 182.17

4, 505 1, 533

1.472⫺5

180.16 422.83

1, 927 11, 72

1.6515 0.811515

1.453015

11.2 175–177 dec 222 dec 98–100 if hydrated; 111 anhyd 163–165 ⫺38

470.73

11, 130

0.858420 4

1.496520

⫺75

28525mm

180.25 334.42

5, 630 272, 723

0.970 1.3620 4

122–124 284–286

307 2705mm

Flash point,⬚C 97

s9 s10

trans-Stilbene (⫺)-Strychnine

s11

Styrene

C6H5CH"CH2

104.15

5, 474

0.906020

1.546320

⫺31

145

31

s12

Styrene oxide

H2C 9 CHC6H5

120.15

17, 49

1.054

1.533820

⫺37

194

79

s13 s14 s15

Succinamic acid Succinamide Succinic acid

O H2NCOCH2CH2CO2H H2NCOCH2CH2CONH2 HO2CCH2CH2CO2H

117.10 116.12 118.09

2, 614 2, 614 2, 601

s16 s17 s18 s19 s20 s21

Succinic anhydride Succinimide Succinonitrile Succinyl chloride Sucrose Sulfadiazine

100.07 99.09 80.09 154.98 342.30 250.28

s22

Sulfamethazine

17, 407 21, 369 2, 615 2, 613 31, 424 Merck: 12, 9071 Merck: 12, 9083

NCCH2CH2CN ClCOCH2CH2COCl

278.34

153–156 265 dec 188

1.552

1.41 0.986460 1.39515 4 1.58725 4

60

1.4173 1.47315

119.6 123–125 54.5 16–17 185–187 252–256 198–201

235 dec 261 285–290 266 190

132 76

s aq; sl s alc; i eth 0.45 aq; i alc, eth 7.7 aq; 5.4 alc; 2.8 acet; 0.88 eth; i bz s alc, chl; v sl s eth 33 aq; 4 alc; i eth see b456 dec by aq, alc; s bz 200 aq; 0.59 alc sl s aq, alc, acet; v s dil mineral acids, alk 0.15 aq; s alk

INTERACTIVE

Squalene

ROTATED

s8

LEFT

L-Sorbose

[(CH3)2CH(CH3)2CH(CH3)(CH2)3CH(CH3)CH2CH2-]2 CH3[C(CH3)"CHCH2CH2]5C(CH3)"C(CH3)2 C6H5CH"CHC6H5

v s alc; misc chl, eth v s aq, alc; i eth s aq; v sl s alc, eth 83 aq; s hot alc, acet

s6 s7

Squalane

Solubility in 100 parts solvent

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Sulfamic acid

HSO3NH2

97.09

s24

Sulfanilamide

H2NC6H4SO2NH2

172.21

Merck: 12, 9090 14, 698

2.15

205 dec

s25

Sulfanic acid

4-(H2N)-C6H4SO3H

173.19

14, 695

d 288

s26 s27

Sulfoacetic acid 2-Sulfobenzoic acid cyclic anhydride

HCO2CH2SO3H

140.11 184.17

4, 21 19, 110

84–86

164–166

Stryene dibromide, d98 Stryene glycol, p108 Stryene oxide, e9 Suberic acid, o25 Suberonitrile, d285

Salicylaldehyde, h94 Solketal, d599 Stearamide, o2 Stearic acid, o5 Stearyl bromide, b385

15 aq; sl s alc, acet; s bases 0.76 aq; 2.7 alc; 20 acet; s acid, alk 1.45 aq; sl s hot MeOH s aq, alc; i eth, chl s bz, chl, eth; i aq

245 dec 18618mm

Succinic acid monoamide, s13 Succinonitrile, b456 Sulfanilic acid, a117 Sulfolane, t107

DEAN 37261 (McGHP)

s23

1.311 s5

s6

s10

s16

RIGHT

s2

s17

ROTATED

s20

s21

s22

s27

INTERACTIVE

No. s28

Name

Formula

Formula weight

Beilstein reference

1.312

6, 865

303–306

(CH3O2CC6H4)2SO2

334.35

102, 109

195–196

(HOC6H4)2SO2 HO3SC6H3(OH)CO2H

250.27 254.21 150.09

6, 861 11, 411 3, 520

1.366315 1.759820 4

245–247 120 anhyd 172–174

150.09

3, 481

1.759820 4

168–170

1.66620 4 ; 1.737 also 1.69720 4

140; also 159–160

meso-Tartaric acid monohydrate

HO2CCH(OH)CH(OH)CO2H · H2O

168.11

3, 528

t4

DL-Tartaric

HO2CCH(OH)CH(OH)CO2H · H2O

168.11

3, 522

534.37 134.13

25, 252 7, 675

C6H2Br4

230.31 230.31 230.31 136.24 136.24 154.25 154.25 393.72

5, 695 52, 611 5, 695 5, 126 5, 128 6, 55 6, 57 5, 214

CH3C6Br4(OH)

423.75

6, 362

Br2CHCHBr2

345.67

1, 94

t7 t8 t9 t10 t11 t12 t13 t14 t15 t16

C6H4-1,4-(CHO)2 C6H5 9C6H4 9C6H5 C6H5 9C6H4 9C6H5 C6H5 9C6H4 9C6H5

Solubility in 100 parts solvent

s alc, eth, acet; i aq v s aq, alc; s eth 139 aq20; 59 MeOH; 33 EtOH; s glyc; 0.4 eth 139 aq20; 59 MeOH; 33 EtOH; s glyc; 0.4 eth 125 aq20

20.6 aq20; 5 alc25; 1 eth

210–212

v s aq

1.195 1.16 1.213 0.837520 4 0.85315 4 0.933820 4 0.933720

1.477520 1.475416 1.482020 1.481320

115–116

245–248

87 56.2 210

363 332 376 174 183 906mm 220

36.4 40.5 180–182

⬎110 ⬎110 46 51 79 90

205–208 2.965520

1.635820

0

misc alc, eth v s alc, eth

s alc, eth, alk 243.5

none

misc alc, chl, eth, HOAc

INTERACTIVE

t3

acid

Flash point,⬚C

ROTATED

L-(⫹)-Tartaric

Boiling point,⬚C

LEFT

t2

t5 t6

Melting point,⬚C

565.88

s30 s31 t1

acid monohydrate Tartrazine Terephthaldicarboxaldehyde m-Terphenyl o-Terphenyl p-Terphenyl ␣-Terpinene ␥-Terpinene Terpinen-4-ol ␣-Terpineol 1,2,4,5-Tetrabromobenzene 3,4,5,6-Tetrabromocresol 1,1,2,2,-Tetrabromoethane

Refractive index

[2,6-(Br)2 9C6H2OH]2SO2

4,4⬘-Sulfonylbis(2,6dibromophenol) 4,4⬘-Sulfonylbis(methyl benzoate) 4,4⬘-Sulfonyldiphenol 5-Sulfosalicylic acid D-(⫺)-Tartaric acid

s29

Density, g/mL

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Tetrabromophthalic anhydride ␣,␣,␣⬘,␣⬘-Tetrabromoo-xylene ␣,␣,␣⬘,␣⬘-Tetrabromom-xylene ␣,␣,␣⬘,␣⬘-Tetrabromop-xylene Tetrabutylammonium bromide Tetrabutylammonium chloride Tetrabutylammonium hydrogen sulfate Tetrabutylammonium iodide Tetrabutylammonium tetrafluoroborate Tetrabutylammonium tribromide

t18 t19 t20 t21 t22 t23 t24 t25

1.313

t26

463.72

17, 485

274–276

sl s bz; i aq, alc

C6H4-1,2-(CHBr2)2

421.77

5, 367

114–116

v s chl

C6H4-1,3-(CHBr2)2

421.77

5, 375

105–108

C6H4-1,4-(CHBr2)2

421.77

5, 386

254–256

(C4H9)4N⫹ Br⫺

322.38

42, 634

102–104

(C4H9)4N⫹ Cl⫺

277.92

43, 292

73–75

(C4H9)4N⫹ HSO⫺4

339.54

(C4H9)4N⫹ I⫺

369.38

4, 157

145–147

(C4H9)4N⫹ BF⫺4

329.28

43, 293

160–162

(C4H9)4N⫹ Br⫺3

482.20

44, 557

74–76

Sulfonyldianiline, d47, d48 Sylvan, m259 Sylvic acid, a1 2,4,5-T, t246

DEAN 37261 (McGHP)

t17

171–173

Taurine, a160 Terephthalaldehyde, b14 Terephthaldicarboxaldehyde, b14 Terephthalic acid, b18

sl s aq; s alc, eth

Terephthaloyl chloride, b16 Tetrabromomethane, c13 Tetrabutoxysilane, t28

RIGHT ROTATED

t1

t2

t5

t10

t11

t12

t13

t17

INTERACTIVE

No. t27 t28 t29 t30 t31 t32 t33

1.314

t34 t35 t36

t37

t40

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

0.820

1.451020

832mm

57

0.89920 4

1.413120

275

78

14510mm 182745mm

107 none

v s acet, chl

46–47

254

⬎110

v s eth; sl s alc

139–142

240–246

⬎110

s bz, chl, eth

{-(CH2)3N[(CH2)3]2}2

340.64

Si[O(CH2)3CH3]4

320.55

[CH3(CH2)3]4PBr

339.35

(C4H9)4Sn Cl2CHC("O)CHCl2

347.15 195.86

1, 656

C6H2Cl4

215.89

5, 204

C6H2Cl4

215.89

5, 205

C6Cl4-1,2-("O)2

245.88

7, 602

127–129

C6Cl4-1,4-("O)2

245.88

7, 636

290 dec

Cl2CFCFCl2

203.83

ClCH2CCl3

167.85

Cl2CHCHCl2 Cl2C"CCl2 HC6Cl4NO2

CH3(CH2)22CH3 CF3(CF2)4CF3 CH3(CH2)12CH3 CH3(CH2)12CO2H CH3(CH2)13OH CH3(CH2)12COCl

12, 398

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

100–103 1.057 1.62415 4

1.474220 1.49718

1.85822

⫺97

s eth; sl s chl; i aq

1.644725

1.413025

26.0

92.8

1, 86

1.540620

1.482120

⫺70.2

130.5

47

167.85

1, 86

1.586625 4

1.491025

⫺44

147

62

165.83 260.89

1, 187 5, 247

1.623020 4 1.74425 4

1.505720

⫺22 98–101

121 304

45

285.90

17, 484

254–258

371

338.66 338.05 198.40 228.38 214.39 246.82

1, 175 13, 388 1, 171 2, 365 1, 428 2, 368

51 ⫺4 5.5 54 39.5 ⫺1

391 58–60 253.6 250100mm 289 16815mm

0.778651 1.669 0.762720 4 0.852570 4 0.815150 0.908

1.428370 1.251520 1.429020 1.427370 1.435850 1.449020

0.012 aq

0.3 aq; misc alc, chl, eth, PE misc alc, chl, eth s alc, bz, chl dec hot aq; sl s eth

⬎110 none 99 ⬎110 ⬎110

9.4 chl; s eth v s alc, eth v s bz, chl, eth; s alc s eth; sl s alc dec aq, alc; s eth

INTERACTIVE

t41 t42 t43 t44 t45 t46

Formula weight

ROTATED

t38 t39

N,N,N⬘,N⬘-Tetrabutyl1,6-hexanediamine Tetrabutyl orthosilicate Tetrabutyl phosphonium bromide Tetrabutyltin 1,1,3,3,-Tetrachloroacetone 1,2,3,4-Tetrachlorobenzene 1,2,4,5-Tetrachlorobenzene Tetrachloro-1,2benzoquinone Tetrachloro-1,4-benzoquinone Tetrachloro-1,2difluoroethane 1,1,1,2-Tetrachloroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene 2,3,5,6-Tetrachloronitrobenzene Tetrachlorophthalic anhydride Tetracosane Tetradecafluorohexane Tetradecane Tetradecanoic acid 1-Tetradecanol Tetradecanoyl chloride

Formula

LEFT

t36a

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

t50 t51 t52 t53 t54 t55 t56 t57

1.315

t58 t59 t60 t61

1-Tetradecene Tetraethoxysilane Tetraethylammonium bromide Tetraethylammonium chloride Tetra(ethylene glycol) Tetra(ethylene glycol) diacrylate Tetra(ethylene glycol) diethyl ether Tetra(ethylene glycol) dimethacrylate Tetra(ethylene glycol) dimethyl ether Tetraethylenepentamine N,N,N⬘,N⬘-Tetraethylethylenediamine Tetraethylgermanium Tetraethyllead Tetraethylsilane N,N,N⬘,N⬘-Tetraethylsulfamide

196.38 208.33 210.16

1, 226 1, 334 4, 104

0.77515 4 0.93420 4 1.39720 4

1.436020 1.38320

(CH3CH2)4N⫹ Cl⫺

165.71

4, 104

1.080121 4

(HOCH2CH2OCH2CH2)2O (H2C"CHCO2CH2CH2OCH2CH2)2O C2H5(OCH2CH2)4OC2H5

194.23 302.33

1, 468

1.12520 20 1.110

1.457720 1.465020

250.34

13, 2107

0.970

[H2C"C(CH3)CO2CH2CH2OCH2CH2]2O CH3(OCH2CH2)4OCH3

330.37

24, 1531

222.28

(H2NCH2CH2NHCH2CH2)2NH

⫺12.9 ⫺77 285 dec

251.2 168

115 46

v s alc, eth dec aq; s alc v s aq, alc, acet, chl 141 aq; s alc; 8.2 chl

⫺6

328

182 ⬎110

misc aq, alc, bz, eth

1.432420

15911mm

⬎110

s aq

1.080

1.463020

220

⬎110

13, 2107

1.008720 4

1.433020

⫺30

275–276

140

s aq

189.31

4,3, 543

0.99920 20

1.505520

⫺40

340

185

misc aq, alc, eth

(C2H5)2NCH2CH2N(C2H5)2

172.32

4, 251

0.808

1.434320

189–192

58

(C2H5)4Ge (C2H5)4Pb (C2H5)4Si (C2H5)2NSO2N(C2H5)2

188.84 323.45 144.34 208.33

4, 631 4, 639 4, 625 4, 129

0.998 1.65320 4 0.765820 1.030

1.442020 1.519020 1.426820 1.448020

165.5 8515mm 154.7 249–251

35 72 26 ⬎110

␣,␣,␣,4-Tetrachlorotoluene, c59 Tetradecyl alcohol, t45

⫺90 ⫺136 ⫺82

Tetraethylmethane, d386a Tetraethyl orthosilicate, t48

s alc, eth; i aq s bz; misc eth i aq

RIGHT

Tetracene, b7 Tetrachloromethane, c14 ␣,␣,␣,2-Tetrachlorotoluene, c58

CH3(CH2)11CH"CH2 (CH3CH2O)4Si (CH3CH2)4N⫹ Br⫺

DEAN 37261 (McGHP)

t47 t48 t49

ROTATED

t40

INTERACTIVE

No. t62 t63 t64 t65 t66 t67 t68

1.316

t69 t70 t71 t72

t74

t76 t77 t78

Beilstein reference

Density, g/mL

Refractive index

[(C2H5)2NC("S)S⫺]2

296.54

4, 122

1.30

(C2H5)4Sn FCH2CF3

234.94 102.03

4, 632 1,4, 123

1.19920

1.473020

F2C"CF2 HCF2CF2CH2OH

100.02 132.06

13, 638 14, 1438

1.151⫺40 1.485320 4

1.319720

C6H9CHO

110.16

71, 48

0.940

1.474520

171.24

20, 416

72.11 132.16

17, 10

0.889220 4 1.154225 4

102.13

172, 106

101.15

Boiling point,⬚C

Flash point,⬚C

71–72 ⫺112 ⫺26.5

181

53

⫺142.5 ⫺15

⫺76 109–110

43

163–164

57

Solubility in 100 parts solvent 3.8 alc; 7.1 eth; s bz, acet, chl; 0.02 aq i aq; s eth

i aq

118–120

325–330

1.405220 1.476625

⫺108.5 ⬍⫺50

65 265

⫺14

1.052420

1.452020

⬍⫺80

178

75

182, 415

0.980

1.456020

154744mm

45

144.17

172, 107

1.061

1.437020

196

84

156.18

173, 1104

1.064

1.460020

879mm

⬎110

120.58

173, 61

1.110

1.455020

150–151

47

170.21

173, 1105

1.044

1.458020

520.4mm

90

1.030

1.461020

186.25

(CH3)2CHCH2CH2CH2C(CH3)(OH)CH2CH3

Melting point,⬚C

97

133.19

20, 275

1.064

1.566820

⫺30

232–233

98

158.29

1, 426

0.826

1.434020

76

736mm

76

misc aq, alc, eth, PE misc aq, alc, bz, chl; s eth misc aq, alc, bz, chl, eth, acet

INTERACTIVE

t79

Formula weight

ROTATED

t75

Tetraethylthiuram disulfide Tetraethyltin 1,1,1,2-Tetrafluoroethane Tetrafluoroethylene 2,2,3,3-Tetrafluoro-1propanol 1,2,3,6-Tetrahydrobenzaldehyde 1,2,3,4-Tetrahydrocarbazole Tetrahydrofuran 2,5-Tetrahydrofurandimethanol Tetrahydro-2-furanmethanol Tetrahydro-2-furanmethylamine Tetrahydrofurfuryl acetate Tetrahydrofurfuryl acrylate Tetrahydrofurfuryl chloride Tetrahydrofurfuryl methacrylate 2(3)-(Tetrahydrofuryloxy)tetrahydropyran 1,2,3,4-Tetrahydroisoquinoline Tetrahydrolinalool

Formula

LEFT

t73

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

t81 t82 t83

1,2,3,4-Tetrahydronaphthalene cis-1,2,3,6-Tetrahydrophthalic anhydride cis-1,2,3,6-Tetrahydrophthalimide Tetrahydropyran

C10H12

132.21

5, 491

152.15

17, 462

0.970220 4

1.541420

Tetraethyl titanate(IV), t163 Tetrafluoromethane, c15 Tetraglyme, b212 1,2,3,4-Tetrahydrobenzene, c368

207.6

77

97–103

151.17 86.14

⫺35.8

misc alc, bz, chl, eth, acet, PE

157

129–133 17, 12

0.881420 4

1.420020

⫺45

Tetrahydrodicyclopentadiene, t259 Tetrahydro-2,5-dimethoxyfuran, d525 Tetrahydrofurfuryl alcohol, t70

⫺155

88

Tetrahydrofurfuralamine, t72 Tetrahydrolinalool, d668 Tetrahydro-2-methylfuran, m429

misc aq, alc, eth

DEAN 37261 (McGHP)

t80

1.317 t68

t69

t71

t74

t72

t75

t76

RIGHT

t73

t70

ROTATED

t77

t78

t81

t82

t83

INTERACTIVE

No. t84 t85 t86 t87 t88 t89 t90

1.318

t91 t92 t93

t95

t97 t98 t99

Beilstein reference

116.16

Density, g/mL

Refractive index

1.025420

1.458020

Melting point,⬚C ⫺70

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

187

93

misc aq, alc, bz, eth

116.19

24, 5

210–212

133.19

20, 262

1.061

1.594020

15–16

249

100

s aq; misc alc, eth

88.17 246.22

171, 5 8, 496

0.998720

1.504020

⫺96 200–203

121

12

misc alc, eth; i aq

[(HO)2C6H3]2C"O [(CH3)2N]2C"C[N(CH3)2]2

200.23

44, 167

0.861

1.480020

590.9mm

53

[CH3CH(OH)CH2]2NCH2CH2N[CH2CH(OH)CH3]2

292.40

44, 1685

1.013

1.481220

1810.8mm

⬎110

(CH3O)2CH(CH2)6CH(OCH3)2

234.34

0.949

1.430020

1305mm

52

[(CH3O)2CH]2CH2

164.20

0.997

1.408120

183

54

(CH3)4N⫹ Br⫺

154.06

4, 51

1.56

⬎300

55 aq

(CH3)4N⫹ Cl⫺

109.60

4, 51

1.16920 4

⬎300

s aq, hot alc

(CH3)4N⫹ I⫺

201.06

4, 51

1.829

⬎300

sl s aq; v s abs alc

(CH3)2C6H3N(CH3)2

149.24

12, 1131

0.913

1.544320

C6H2-1,2,3,4-(CH3)4

134.22

5, 430

0.90520 4

1.518720

C6H2-1,2,3,5-(CH3)4

134.22

5, 430

0.890620 4

1.513420

C6H2-1,2,4,5-(CH3)4

134.22

5, 431

(CH3)3CC(CH3)3

114.23

1, 165

226–228

90

⫺6.2

205.0

68

misc alc, eth

⫺23.7

198.0

63

s alc; v s eth

0.83881 4

79.3

196.8

73

v s alc, bz, eth

0.824220

⫺100.7

106.5

4

INTERACTIVE

t100

Formula weight

ROTATED

t96

Tetrahydropyran-2methanol 3,4,5,6-Tetrahydropyrimidinethiol 1,2,3,4-Tetrahydroquinoline Tetrahydrothiophene 2,2⬘,4,4⬘-Tetrahydroxybenzophenone Tetrakis(dimethylamino)ethylene N,N,N⬘,N⬘-Tetrakis(2hydroxypropyl)ethylenediamine 1,1,8,8-Tetramethoxyoctane 1,1,3,3-Tetramethoxypropane Tetramethylammonium bromide Tetramethylammonium chloride Tetramethylammonium iodide N,N-3,5-Tetramethylaniline 1,2,3,4-Tetramethylbenzene 1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene 2,2,3,3-Tetramethylbutane

Formula

LEFT

t94

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

t102

t103 t104 t105

t106 t107

1.319

t108

t109 t110

N,N,N⬘,N⬘-Tetramethyl-1,3-butanediamine N,N,N⬘,N⬘-Tetramethyl-1,4-butanediamine 1,1,3,3-Tetramethylbutylamine 1,3,5,7-Tetramethylcyclotetrasiloxane N,N,N⬘,N⬘-Tetramethyldiaminomethane 1,1,3,3-Tetramethyldisiloxane Tetramethylene sulfone

(CH3)2NCH(CH3)CH2CH2N(CH3)2

144.26

43, 570

0.787

1.431820

165

40

(CH3)2N(CH2)4N(CH3)2

144.26

4, 265

0.78620

1.428020

169

46

s aq, alc, eth

(CH3)3CCH2C(CH3)2NH2

129.25

4, 198

0.805

1.424020

137–143

32

s alc, eth, PE; i aq

[-SiH(CH3)O-]4

240.51

44, 4099

0.991220 4

1.387020

(CH3)2NCH2N(CH3)2

102.18

4, 54

0.749

1.400520

85

⫺12

[(CH3)2CH]2O

134.33

44, 3991

0.75720 4

1.370020

70–71

⫺10

120.17

171, 5

1.260630 4

1.482030

27.6

285

177

N,N,N⬘,N⬘-Tetramethylethylenediamine Tetramethylgermanium 1,1,3,3-Tetramethylguanadine

(CH3)2NCH2CH2N(CH3)2

116.21

4, 250

0.770

1.417920

⫺55

120–122

10

(CH3)4Ge

132.73

4,2, 1008

0.978

1.389020

⫺88

43.4

⫺37

[(CH3)2N]2C"NH

115.18

41, 335

0.918

1.469220

163

60

⫺69

Tetramethyl glycol, b457 Tetramethylene oxide, t69 Tetramethylene sulfide, t87 Tetramethylethylene glycol, d569

misc aq, acet, toluene; s octanes, olifines, naphthenes

RIGHT

␤-Tetralonehydantoin, b40 N,N,N⬘,N⬘-Tetramethyldiaminomethane, t113 N,N,N⬘,N⬘-Tetramethyl-1,3-diamino-2-propanol, b180 2,2,5,5-Tetramethyl-3,4-dithiahexane, d171 Tetramethylene, c333

Tetrahydropyrrole, p280 6,7,8,9-Tetrahydro-5H-tetrazolazepine, p27 Tetrahydrothiophene 1,1-dioxide, t107 Tetraiodomethane, c16 Tetralin, t80

134–135

DEAN 37261 (McGHP)

t101

ROTATED

t84

t85

t86

t87

t107

INTERACTIVE

No. t111

t112 t113

t114 t115

1.320

t116

t117 t118 t119

t123 t124

t125

Beilstein reference

Density, g/mL

Refractive index

N,N,N⬘,N⬘-Tetramethyl-1,6-hexanediamine Tetramethyl lead N,N,N⬘,N⬘-Tetramethylmethanediamine 2,6,10,14-Tetramethylpentadecane 2,2,6,6-Tetramethylpiperidinyl-1-oxy (free radical) N,N,N⬘,N⬘-Tetramethyl-1,3-propanediamine Tetramethylpyrazine Tetramethylsilane 1,1,3,3-Tetramethyl2-thiourea

[(CH3)2N(CH2)3-]2

172.32

41, 423

0.806

1.435920

(CH3)4Pb (CH3)2NCH2N(CH3)2

267.33 102.18

4, 639 4, 54

1.99520 4 0.749

1.400520

[(CH3)2CH(CH3)3CH(CH3)CH2]2CH2

268.53

Merck: 12, 7932

0.782720 4

1.438520

Tetramethylthiuram disulfide Tetramethyltin 1,1,3,3-Tetramethylurea Tetranitromethane 1,4,7,10-Tetraoxacyclododecane (12-Crown-4) 2,4,8,10-Tetraoxaspiro[5.5]undecane Tetraphenylboron sodium

156.25

Boiling point,⬚C

130.24

4, 262

0.779

1.423420

(CH3)4Si (CH3)2NC("S)N(CH3)2

136.20 88.23 132.23

23, 99 4, 625 41, 336

0.641120 4

1.358020

[(CH3)2NCS2-]2

240.43

4, 76

1.29

(CH3)4Sn (CH3)2NC("O)N(CH3)2

178.83 116.16

4, 631 4, 74

1.314925 0.968720 4

1.5201 1.449325

C(NO2)4

196.03 176.21

1, 80

1.622925 4 1.089

1.435825 1.463020

160.17 342.23

Flash point,⬚C

Solubility in 100 parts solvent

209–210

73

⫺27.5

110 85

38 ⫺12

misc alc, eth

⫺100

296

⬎110

s bz, chl, eth, PE

36–40

(CH3)2N(CH2)3N(CH3)2

(C6H5)4B⫺ Na⫹

Melting point,⬚C

67

145–146

31

190 26.5 245

⫺27

⫺54 ⫺0.6

74–75 176–177

⫺12 77

13.8 16

126 700.5mm

⬎110 ⬎110

19, 436

52–55

831.5mm

108

Merck: 12, 8839

⬎300

84–86 ⫺99.5 75–77

v s alc, eth 0.002 alc, 0.002 eth; 0.012 acet; 0.025 bz; s chl

155–156

misc aq, common org solvents v s alc, eth, alk

v s aq, acet; s chl

INTERACTIVE

t126

Formula weight

ROTATED

t121 t122

Formula

LEFT

t120

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

t128 t129 t130 t131 t132 t133

1,1,4,4-Tetraphenyl1,3-butadiene Tetraphenyltin Tetrapropoxysilane Tetrapropylammonium bromide 1H-Tetrazole 2-Thenoyltrifluoroacetone Theobromine

(C6H5)2C"CHCH"C(C6H5)2

358.49

5, 750

(C6H5)4Sn (C3H7O)4Si (CH3CH2CH2)4N⫹ Br⫺

427.11 264.4 266.27

1, 355 41, 364

Tetramethylolmethane, p19 2,2,4,4-Tetramethyl-3-thiapentane, d147 Tetramethylthiuram disulfide, b183

70.06 222.18

26, 346

180.17

26, 457

207–209 1.4900 0.91624

224–227 1.40120

⬎420 945mm

110 95

270 dec 157–158 40–44 357

Tetrantoin, b40 2,5,8,13-Tetraoxododecane, b211 Tetraphene, b6

s aq s aq, alc, acet 988mm sublimes 290– 295

100 aq; 0.045 alc; s alk; i bz, chl, eth

DEAN 37261 (McGHP)

t127

Tetrapropoxytitanate(IV), t163 2-Thenoic acid, t155

1.321 t117

t124

t125

t131

RIGHT

t115

ROTATED

t132

t133

INTERACTIVE

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

Melting point,⬚C

1.322

26, 455

274–275

t135

Thiamine HCl

337.27

dec 260

t136 t137

Thiazole N2-(2-Thiazolyl)sulfanilamide

85.13 255.32

Merck: 12, 9430 27, 15 273, 4623

t138 t139 t140

CH3C("S)NH2 C6H5C("O)SH

75.13 138.19 358.54

2, 232 9, 419 64, 6043

C6H5NHC("S)NHC6H5 HSC6H4CH3 (HO2CCH2)2S (HOCH2CH2)2S (HOC6H4)2S (HO2CCH2CH2)2S

228.32 124.21 150.15 122.19 218.27 178.21

12, 394 6, 416 3, 253 1, 470 6, 860

t147 t148 t149

Thioacetamide Thiobenzoic acid 4,4⬘-Thiobis(2-tertbutyl-6-methylphenol) Thiocarbanilide p-Thiocresol 2,2⬘-Thiodiacetic acid 2,2⬘-Thiodiethanol 4,4⬘-Thiodiphenol 3,3⬘-Thiodipropionic acid Thiolacetic acid N-Thionylaniline Thionyl bromide

CH3C("O)SH C6H5N"SO SOBr2

76.12 139.18 207.88

1.065 1.236 2.683

1.4630 1.627020 1.675020

t150

Thionyl chloride

SOCl2

118.97

1.635

t151 t152 t153

Thiophene 2-Thiopheneacetic acid 2-Thiophenecarbonyl chloride 2-Thiophenecarboxaldehyde

C4H4S (C4H3S)CH2CO2H (C4H3S)COCl

84.14 142.18 146.60

2, 230 12, 578 Merck: 12, 9484 Merck: 12, 9485 17, 29 18, 293 18, 290

(C4H3S)CHO

112.15

17, 285

t141 t142 t143 t144 t145 t146

t154

1.200

1.539020

0.83 aq; 1.25 alc; 0.9 chl; s hot aq, alk, dil acids 100 aq; 1 alc; 5.5 glyc 117–118

22

12230mm 31640mm

⬎110 240

195

68

282

160

202

1.174

1.605020

1.3224

1.182420 4

1.520320

112–114 15–18 163–165

152–155 42–44 128–131 ⫺10.2 154–156 131–134 ⬍ ⫺17

11 84

⫺52

88–91 200 138

1.51720

⫺101

76

none

1.057325 4

1.525725

⫺39.4 63–67

⫺1

1.371

1.590020

84 16022mm 206–208

1.200

1.590020

198

77

s alc, eth; sl s aq 0.06 aq; 0.52 alc; s acet, dil mineral acids, alkalis 16 aq; 16 alc; sl s eth misc eth; v s alc; i aq

v s alc, eth s alc, eth; i aq s aq, alc misc aq, alc; sl s eth 3.7 aq; v s hot aq, alc, acet s aq; v s alc misc bz, chl, CCl4; hyd by aq misc bz, chl, CCl4; hyd by aq misc alc, eth; i aq

90 s eth

INTERACTIVE

180.17

Solubility in 100 parts solvent

ROTATED

Theophylline

Flash point,⬚C

LEFT

t134

Boiling point,⬚C

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

t156 t157 t158

2-Thiophenecarboxylic acid Thiophenol Thiophenoxyacetic acid Thiophosphoryl chloride

(C4H3S)CO2H

128.15

18, 289

C6H5SH C6H5SCH2CO2H

110.18 168.21

6, 294 6, 313

PSCl3

169.40

260

s aq, chl; v s alc, eth

1.073

1.588020

⫺14.9 64–66

169

50

v s alc; misc bz, eth

1.668

1.555020

⫺36 (␤) ⫺40 (␣)

125

none

s bz, chl, CCl4, CS2

2-Thiapentane, m406 3-Thiapentane, d398 Thioanisole, m379 2-Thiobarbituric acid, d437 1,1⬘-Thiobis(butane), d170 Thiocarbanilide, d791 2,2⬘-Thiodiethanethiol, b209

2-Thiabutane, e221 Thiacyclopentane, t87 1,3,4-Thiadiazole-2,5-dithiol, d486 3-Thiaheptane, b557 2-Thiahexane, b577 3-Thiahexane, e255 Thianaphthene, b60 5-Thianonane, d170

127–130

Thiodiethylene glycol, t144 Thiodiglycol, t144 Thiodiglycolic acid, t143 Thioethanol, e26a Thioethanolamine, a161 1-Thioglycerol, m21 Thioglycolic acid, m16

DEAN 37261 (McGHP)

t155

1.323 t135

t136

RIGHT

t134

ROTATED

t137

t140

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

Name

Formula

Formula weight

Beilstein reference

1.324

t163 t164

Titanium(IV) ethoxide Titanium(IV) isopropoxide Titanium(IV) propoxide Toluene 2,4-Toluenediamine 2,5-Toluenediamine 2,6-Toluenediamine 3,4-Toluenediamine Toluene-2,4-diisocyanate p-Toluenesulfinic acid o-Toluenesulfonamide p-Toluenesulfonamide p-Toluenesulfonylhydrazide p-Toluenesulfonic acid p-Toluenesulfonyl chloride p-Toluenesulfonyl fluoride

CH3C6H3-2,4-(NH2)2 CH3C6H3-2,5-(NH2)2 CH3C6H3-2,6-(NH2)2 CH3C6H3-3,4-(NH2)2 CH3C6H3-2,4-(NCO)2

122.17 122.17 122.17 122.17 174.16

13, 13, 13, 13, 13,

CH3C6H4SO2H CH3C6H4SO2NH2 CH3C6H4SO2NH2

156.21 171.22 171.22

11, 9 11, 86 11, 104

t165 t166 t167 t168 t169 t170 t171 t172 t173 t174 t175 t176 t177 t178

1.014

1.464020

90.14 91.14 76.12 212.27 150.22

2, 264 3, 195 3, 180 17, 357 6, 532

1.405 0.969925 4

Ti(OC2H5)4 Ti[OCH(CH3)2]4

228.15 284.26

1, 335 12, 382

Ti(OCH2CH2CH3)4

284.26

C6H5CH3

92.14

Boiling point,⬚C 108–110

Flash point,⬚C 11

1.522720

182–184 176–178 212–213 51.5

373715mm 233

102

1.088 0.963

1.504320 1.466020

18–20

15210mm 220

28 22

13, 1423

1.033

1.498620

1703mm

42

5, 280

0.866020 4

1.496020

⫺94.9

110.6

4

292 273–274

1.568920

99 64 104–106 91–93 20–21

124 144 148 148 138

2

1.224420 4

15618mm 251

Solubility in 100 parts solvent

132

85 156–158 138–140

s aq, alc 9 aq; s alc; sl s eth v s bz, chl, hot HOAc 0.1 aq; 100 alc; 140 eth; s HOAc, alk OH s bz, chl, eth

misc alc, chl, eth, acet, HOAc; 0.067 aq s hot aq, alc, eth v s aq, alc, eth s aq, alc v s aq dec aq, alc; misc acet, bz, eth v s alc, eth; sl s aq 0.2 aq; 3.6 alc

CH3C6H4SO2NHNH2

186.23

11 , 66

110 dec

CH3C6H4SO3H CH3C6H4SO2Cl

172.20 190.65

11, 97 11, 103

107 anhyd 67–69

14020mm 13410mm

CH3C6H4SO2F

174.19

112, 54

41–42

11216mm

67 aq; s alc, eth v s alc, bz, eth; i aq 105

INTERACTIVE

CH3CH2C("O)SH H2NC("S)NHNH2 H2NC("S)NH2

Melting point,⬚C

ROTATED

Thiopropionic acid 3-Thiosemicarbazide Thiourea Thioxanthen-9-one Thymol

Refractive index

LEFT

t159 t160 t161 t162 t162a

Density, g/mL

t180 t181 t182 t183 t184 t185 t186 t187 t188 t189 t190 t191 t192 t193

1.325

t194 t195

p-Toluenesulfonyl isocyanate m-Toluidine o-Toluidine p-Toluidine m-Tolunitrile o-Tolunitrile p-Tolunitrile 2-(p-Toluoyl)benzoic acid m-Toluoyl chloride o-Toluoyl chloride p-Toluoyl chloride p-Tolyl acetate 1-(o-Tolyl)biguanide m-Tolyl isocyanate 1,2,4-Triacetoxybenzene Triacetoxyvinylsilane Triallylamine

197.21

CH3C6H4NH2 CH3C6H4NH2 CH3C6H4NH2 CH3C6H4CN CH3C6H4CN CH3C6H4CN CH3C6H4COC6H4CO2H

107.16 107.16 107.16 117.15 117.15 117.15 240.26

12, 853 12, 772 12, 880 9, 477 9, 466 9, 489 10, 759

0.98920 4 0.99820 0.961920 0.97615 0.989 0.978530 4

1.568020 1.572020 1.553259 1.525620 1.527920

CH3C6H4COCl CH3C6H4COCl CH3C6H4COCl CH3CO2C6H4CH3 CH3C6H4NHC("NH)NHC("NH)NH2 CH3C6H4NCO C6H3(O2CCH3)3

154.60 154.60 154.60 150.18 191.24

9, 477 9, 464 9, 484 6, 397 123, 1873

1.173 1.185 1.169 1.048

1.548520 1.554920 1.553020 1.501020

133.15 252.22

12, 864 6, 1089

1.033

(CH3CO2)3SiCH"CH2 (H2C"CHCH2)3N

232.26 137.23

4, 208

⫺2

⬎110

203 200 200 210 205 217

85 (CC) 85 87 86 84 85

865mm 9012mm 225–227 210–211

76 76 82 90 ⬎110

7612mm

65

12825mm

76 30

143–145 1.530520

misc alc, eth 1.7 aq; s alc, eth 7.4 aq; v s alc, eth 0.09 aq; v s alc, eth i aq; misc alc, eth i aq; v s alc, eth v s alc, bz, eth, acet

s alc, eth; i aq

98–100 1.167 0.790

1.422020 1.451020

Tioxolone, h105 TMS, t118 TMSi, t396 Tolan, d742 p-Tolualdehyde, m138 Toluenethiol, t142

150–151

Toluic acids, m142 thru 144 ␣-Tolunitrile, p82 p-Tolylacetamide, m374 Tolyl bromide, b431 ␣-Tolyl chloride, b90 Tolyl chlorides, c255 thru c257

OH H3C

CH3

ROTATED

CH3

t162

⫺31 ⫺16.3 43.8 ⫺23 ⫺13 29.5 137–139

14410mm

RIGHT

Thiolactic acid, m22 Thiomalic acid, m25 Thiosalicylic acid, m18 Thiosinamine, a97 2-Thioxo-4-thiazolidinone, r7 Threonine, a185 Tiglic acid, m169

1.435520

CH3C6H4SO2NCO

DEAN 37261 (McGHP)

t179

t162a

INTERACTIVE

No. t196

t197 t198 t199 t200 t201 t202 t203 t204

1.326

t205 t206 t207 t208 t209 t210

Beilstein reference

249.27

Density, g/mL

Refractive index

1.159

1.512920

(C6H5CH2)3N Br3CCHO Br3CCO2H Br3C6H2NH2 Br3CCH2OH BrCH"CBr2

69.07 287.41 280.76 296.76 329.83 282.77 264.74

26, 13 12, 1038 1, 626 2, 220 12, 663 12, 338 1, 191

1.70821

1.624725

CHBr3

252.77

1, 68

2.900015

2,4,6-Tribromophenol 1,2,3-Tribromopropane Tributoxyborane Tributylamine Tributylborane 2,4,6-Tri-tert-butylphenol Tributyl phosphate Tributyl phosphite Tributyltin chloride Tributyltin ethoxide Tributyltin hydride Tributyltin methoxide Trichloroacetamide Trichloroacetaldehyde

Br3C6H2OH BrCH2CH(Br)CH2Br (C4H9O)3B (C4H9)3N (C4H9)3B [(CH3)3C]3C6H2OH

330.82 280.78 230.16 185.36 182.16 262.44

6, 203 1, 112 12, 398 4, 157 42, 1022

2.55 2.390 0.856720 0.7784 0.747 0.86427 4

(C4H9O)3P(O) (C4H9O)3P (C4H9)3SnCl (C4H9)3SnOC2H5 (C4H9)3SnH (C4H9)3SnOCH3 Cl3CCONH2 Cl3CCHO

266.32 250.32 325.49 335.10 291.05 321.07 162.40 147.40

12, 397 11, 187 43, 1926

Trichloroacetic acid Trichloroacetic anhydride 1,1,3-Trichloroacetone Trichloroacetonitrile

Cl3CCO2H (Cl3CCO)2O

163.39 308.75

44, 4312 44, 4331 2, 211 Merck: 12, 9755 2, 206 2, 210

ClCH2COCHCl2 Cl3CCN

161.42 144.39

1, 655 2, 212

0.99195 4 2.665

Melting point,⬚C

Boiling point,⬚C 1524mm

119–121 91–94 1.585020

Flash point,⬚C ⬎110

260 65 65

130–133 120–122 73–79

174 245 300 9310mm 162.5

1.600515

8.1

149.6

83

1.58418 1.409220 1.428020

87–89 16.5 ⬍⫺70 ⫺70

290746mm 220 234 216 10920mm 277

93 93 86 ⫺36

2.35

129–132

0.972725 0.92520 4 1.200 1.098 1.082 1.115

1.422625 1.432620 1.490520 1.467220 1.473020 1.472020

1.51020 4

1.455720

1.62961 4 1.690

1.620020 1.483820

1.508 1.440325 4

1.489220 1.440920

⫺79

289 1257mm 17325mm 920.1mm 800.4mm 970.06mm 238–240 97.8

146 91 ⬎110 40 40 98

57.5

196.5 14160mm

⬎110 none

13–15 ⫺42

172 86

79 none

141–143 ⫺57.5

Solubility in 100 parts solvent

s aq, alc s hot alc, eth s aq, alc, chl, eth s aq, alc, eth s hot alc, chl, eth 2 aq; s alc, bz, eth

0.3 aq; misc eth, MeOH s alc, chl, eth; i aq s alc, eth hyd aq v s alc, eth; s acet i aq; s most org solv

0.04 aq; misc org solv misc alc, bz, eth, PE

dec aq, alc; s eth 120 aq; v s alc, eth

INTERACTIVE

t221 t222

Formula weight

ROTATED

t219 t220

Triallyl-1,3,5-triazine2,4,6(1H,3H,5H)trione 1H-1,2,4-Triazole Tribenzylamine Tribromoacetaldehyde Tribromoacetic acid 2,4,6-Tribromoaniline 2,2,2-Tribromoethanol 1,1,2-Tribromoethylene Tribromomethane

Formula

LEFT

t211 t212 t213 t214 t215 t216 t217 t218

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

t224 t225 t226 t227 t228 t229 t230 t231 t232 t233 t234 t235

1.327

t236 t237 t238 t239

2,2⬘,4⬘-Trichloroacetophenone Trichloroacetyl chloride 2,4,5-Trichloroaniline 2,4,6-Trichloroaniline 1,2,3-Trichlorobenzene 1,2,4-Trichlorobenzene 1,3,5-Trichlorobenzene Trichloro-3-chloropropylsilane 1,1,1-Trichloroethane 1,1,2-Trichloroethane 2,2,2-Trichloroethanol 2,2,2-Trichloroethyl chloroformate Trichloroethylene

Cl2C6H3COCH2Cl

223.49

7, 283

Cl3CCOCl

181.83

2, 210

Cl3C6H2NH2 Cl3C6H2NH2 C6H3Cl3 C6H3Cl3 C6H3Cl3 Cl(CH2)3SiCl3

196.46 196.46 181.45 181.45 181.45 211.98

12, 627 12, 627 5, 203 5, 204 5, 204

CH3CCl3 ClCH2CHCl2 Cl3CCH2OH ClCO2CH2CCl3

133.41 133.41 149.40 211.86

ClCH"CCl2

Trichloroethylsilane Trichlorofluoromethane ␣,␣,2-Trichloro-6fluorotoluene Trichloroisocyanuric acid

1354mm

⫺146

118

93–95 73–75 53–55 17 63.5

270 262 218–220 213–214 208 181–183

⬎110

s alc s alc, eth v s bz, CS2; sl s alc misc bz, eth, PE v s bz, eth, PE

1.69 1.45420 1.66 1.350

1.577620 1.570720 1.566219 1.466620

1, 85 1, 85 1, 338

1.339020 1.439720 1.557 1.539

1.437920 1.471420 1.490020 1.470320

⫺30.4 ⫺37 18

74 114 151–153 171–172

⫺1 32

s acet, bz, eth misc alc, eth 8 aq; misc alc, eth

131.39

1, 187

1.464220

1.477320

⫺84.8

87

32

0.1 aq; misc alc, chl, eth

C2H5SiCl3 Cl3CF

163.51 137.37

1.237320 1.48521

1.425620 1.38420

⫺105.6 ⫺111

100.5 23.8

22

ClC6H3(F)CHCl2

213.47

4, 630 Merck: 12, 9770 53, 701

1.446

1.550620

228–230

⬎110

232.41

25, 256

126 110 107

0.14 aq; s alc, eth

249–251

Tributyl borate, t207 Tributyrin, g20

Trichloroethanal, t218 ␤,␤,␤-Trichloroethoxycarbonyl chloride, t234

RIGHT

Triacetin, p200 1,3,5-Triazine-2,4,6-triol, c332

1.468920

1.629

52–55

DEAN 37261 (McGHP)

t223

ROTATED

t196

t197

t239

INTERACTIVE

No. t240

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

1.70020 4

1.543620

(CH3)2C(OH)CCl3

177.46

1, 382

CH3SiCl3 Cl3C6H2NO2

149.48 226.45

43, 1896 5, 246

Cl3C6H2OH

197.45

62, 180

t245

2,4,6-Trichlorophenol

Cl3C6H2OH

197.45

6, 190

t246

(2,4,5-Trichlorophenoxy)acetic acid 1,2,3-Trichloropropane 2,4,6-Trichloropyrimidine Trichlorosilane

Cl3C6H2OCH2CO2H

255.49

63, 702

ClCH2CH(Cl)CH2Cl

147.43 183.43

1, 106 23, 90

1.388920

1.485420 1.570020

HSiCl3

135.45

1.342

1.400020

4-(Trichlorosilyl)butyronitrile ␣,␣,␣-Trichlorotoluene ␣,2,4-Trichlorotoluene ␣,2,6-Trichlorotoluene ␣,3,4-Trichlorotoluene 2,4,6-Trichloro-1,3,5triazine 1,1,1-Trichlorotrifluoroethane 1,1,2-Trichlorotrifluoroethane Trichlorovinylsilane

Cl3Si(CH2)3CN

202.54

Merck: 12, 9776 4,4, 4272

1.300

1.463020

C6H5CCl3 Cl2C6H3CH2Cl Cl2C6H3CH2Cl Cl2C6H3CH2Cl

195.48 195.48 195.48 195.48 184.41

5, 300 54, 819

1.372320 1.407

5, 300 26, 35

1.411

1.558020 1.576020 1.576120 1.576620

t241 t242 t243

1.328

t247 t248 t249 t250 t251 t252 t253 t254 t255 t256 t257 t258

Cl3CCF3

187.38

Cl2CFCClF2

187.38

H2C"CHSiCl3

161.49

13, 157

1.27320 4 1.79020

1.410820

1.490175 4

Solubility in 100 parts solvent

146–148 99 anhyd

167

s alc, bz, chl, eth

⫺90 49–55

66 288

67–69

253

69

246

none

615 acet; 163 bz; 525 eth; 615 MeOH; i aq 525 acet; 113 bz; 354 eth; 525 MeOH; i aq s alc; v sl s aq

⫺14.7 23–25

157 ⬎110

71

misc alc, eth; i aq

⫺127

31–32

⫺13

dec aq; s bz, chl

237–238

92 127 ⬎110 ⬎110 ⬎110

146–148

219–223 248 11914mm 12414mm 190

⫺9 ⬎110

154–158

⫺5 ⫺2.6 36–39

1.579

1.369920

13–14

46

1.563525

1.355725

⫺35

47.7

1.270

1.436020

⫺95

90

v s bz, eth

s alc, bz, eth v s alc, eth i aq; s alc

0.017 aq 10

INTERACTIVE

3, 135

Flash point,⬚C

ROTATED

185.89

Boiling point,⬚C

LEFT

Cl3CSCl

t244

Trichloromethanesulfenyl chloride 1,1,1-Trichloro-2methyl-2-propanol Trichloromethylsilane 1,2,4-Trichloro-5nitrobenzene 2,4,5-Trichlorophenol

Melting point,⬚C

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

Tricyclo[5.2.1.02,6]decane Tricyclo[5.2.1.02,6]decan-8-one Tridecane Tridecanoic acid 2-Tridecanone 7-Tridecanone 1-Tridecene Triethanolamine

136.24

5, 164

150.22

72, 133

1.063

1.502520

CH3(CH2)11CH3 CH3(CH2)11CO2H CH3(CH2)10COCH3 [CH3(CH2)5]2CO CH3(CH2)10CH"CH2 (HOCH2CH2)3N

184.37 214.35 198.35 198.35 182.35 149.19

1, 171 2, 364 1, 715 1, 715 1, 225 4, 285

0.756320 4

1.425620

0.822 0.825 0.765820 1.124220 4

1.435020

(C2H5O)3C6H2CO2H

254.29

10, 481

(C2H5O)3B (C2H5O)3SiH (C2H5O)3SiCH2CH2CN

145.99 164.28 217.34

1, 335 1, 334 44, 4271

(C2H5O)3Si(CH2)3NCO

247.37

t272 t273 t274

3,4,5-Triethoxybenzoic acid Triethoxyborane Triethoxysilane 3-(Triethoxysilyl)propionitrile 3-(Triethoxysilyl)propyl isocyanate Triethoxyvinylsilane Triethylaluminum Triethylamine

(C2H5O)3SiCH"CH2 (C2H5)3Al (C2H5)3N

190.32 114.17 101.19

t275 t276 t277

Triethylantimony Triethylarsine Triethylborane

(C2H5)3Sb (C2H5)3As (C2H5)3B

208.94 162.11 98.00

t260 t261 t262 t263 t264 t265 t266 t267 t268 t269 t270 t271

1.329

1.434020 1.485320

193

40

13230mm ⫺5 to ⫺4 41–42 29–31 30–32 ⫺13 20.5

235 236100mm 13410mm 264 232.8 335.4

70 ⬎110 ⬎110 ⬎110 79 179

v s alc, eth v s alc, eth; i aq

dec aq

s alc; v s eth misc aq, alc, acet; 4.5 bz; 1.6 eth; s chl

110–112 0.864 0.890 0.979

1.374020 1.377020 1.414020

117–118 134–135 224

11 26 100

0.999

1.420020

283

77

0.90320 4 0.83225 0.727520

1.397820

4, 643 4, 99

1.401020

⫺50 ⫺114.7

160–161 194 88.8

34 ⫺18 ⫺7

4, 618 4, 602 4, 641

1.32416 1.15020 4 0.696123

1.42

⫺29

1.397020

⫺02.9

159.5 140736mm 95

dec aq, air 5.5 aq; misc alc, eth; s acet, EtOAc i aq; misc alc, eth i aq; dec by air

Tricyclo[5.2.1.02,6]decane-4,8-dimethanol, b202 3-Triethoxysilylpropylamine, a273 Triethyl borate, t268

Tricine, t441 Tri-o-cresyl phosphate, t452 Tricyclene, t400a Tricyclo[3.3.1.13,7]decane, a65

RIGHT

Trichloromethane, c145 (Trichloromethyl)benzene, t251 Tricyclophenylsilane, p159 3,3,3-Trichloropropylene oxide, e18

77–79

DEAN 37261 (McGHP)

t259

ROTATED

t248

t255

t259

t260

INTERACTIVE

No.

Name

Formula HOC(CO2C2H5)(CH2CO2C2H5)2

t280 t281

t292 t293

Tri(ethylene glycol) Tri(ethylene glycol) dimethacrylate Tri(ethylene glycol) dimethyl ether Tri(ethylene glycol) divinyl ether Tri(ethylene glycol) monomethyl ether Triethylenetetramine Triethylgallium 1,3,5-Triethylhexahydro-1,3,5-triazine Triethylindium Triethyl orthoacetate Triethyl orthoformate Triethyl orthopropionate Triethyl phosphate Triethylphosphine

t294 t295

t282 t283 t284

1.330

t285 t286 t287 t288 t289 t290 t291

t296

Refractive index 1.442020

Melting point,⬚C

Boiling point,⬚C 1271mm

Flash point,⬚C ⬎110 62

Solubility in 100 parts solvent

276.29 112.18

3, 568 233, 484

1.137

(HOCH2CH2OCH2-)2 [H2C"C(CH3)CO2CH2CH2OCH2-]2 (CH3OCH2CH2OCH2-)2

150.17 286.33

1, 468 24, 1531

1.127415 1.092

1.455020 1.460520

⫺7

285 1725mm

177 ⬎110

178.23

0.99020 4

1.422420

⫺45

216

111

H2C"CH(OCH2H2)3OCH"CH2

202.25

Merck: 12, 9820 13, 2106

0.990

1.453020

12618mm

⬎110

CH3(OCH2CH2)3OH

164.20

13, 2105

1.026

1.439920

12210mm

⬎110

(H2NCH2CH2NHCH2-)2 (C2H5)3Ga

146.24 156.91 171.20

4, 255

1.4971

266 142.6 207–208

143

26, 2

0.982 1.057630 0.894

80

144 142 146 155–160

36 30 60

misc alc, chl, eth dec aq; s alc, eth v s alc, eth

215 128–129

115 ⫺17

s aq(dec), alc, eth i aq; misc alc, eth; pyrophoric i aq(hyd); misc alc, acet, bz, eth, PE

158–160

12 ⫺82.3

1.459520

(C2H5)3In CH3C(OC2H5)3 HC(OC2H5)3 CH3CH2C(OC2H5)3

202.01 162.23 148.20 176.26

1.26020 0.884725 4 0.89120 4 0.876

1.53820 1.395025 1.391020 1.399520

⫺32

2, 129 2, 20 2, 240

(C2H5O)3P(O) (C2H5)3P

182.16 118.16

1, 332 4, 582

1.069520 0.80015 4

1.405820 1.456320

⫺56 ⫺88

Triethyl phosphite

(C2H5O)3P

166.16

1, 330

0.96920 4

1.413020

156

54

Triethyl phosphonoacetate Triethyl phosphonoformate Triethylsilane Triethyl thiophosphate 2,2,2-Trifluoroacetamide

(CH3CH2O)2P(O)CH2CO2C2H5

224.19

41, 573

1.130

1.431020

1459mm

⬎110

(CH3CH2O)2P(O)CO2C2H5

212.17

32, 103

1.110

1.432020

13512mm

⬎110

(C2H5)3SiH (C2H5O)3P(S) CF3CONH2

116.28 198.22 113.04

4, 625 1, 333 22, 186

0.73120 4 1.082

1.41220 1.448020

107–108 10016mm 162.5

⫺3 107

⫺76

70–75

45 aq; 13 acet; 77 alc; 51 bz misc aq, alc, bz

misc aq, hydrocarbon solvents

i aq; misc alc, eth

INTERACTIVE

t297 t298 t299

Density, g/mL

ROTATED

Triethyl citrate Triethylenediamine

Beilstein reference

LEFT

t278 t279

Formula weight

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

t302 t303 t304 t305 t306 t307 t308 t309 t310

1.331

t311 t312 t313 t314 t315

Trifluoroacetic acid Trifluoroacetic anhydride 1,1,1-Trifluoroacetone 1,3,5-Trifluorobenzene ␣,␣,␣-Trifluoro-mcresol 2,2,2-Trifluoroethanol 2,2,2-Trifluoroethyl trifluoroacetate Trifluoromethane Trifluoromethanesulfonic acid Trifluoromethanesulfonic anhydride 3-(Trifluoromethyl)aniline ␣,␣,␣-Trifluorotoluene Trihexyl O-acetylcitrate Trihexylamine Trihexyl O-butylcitrate Trihexylchlorosilane

CF3CO2H [CF3C(O)]2O

114.02 210.03

22, 186 22, 186

1.489020 1.487

1.285020 ⬍1.300

⫺15.3 ⫺65

73 39–40

CF3C(O)CH3 C6H3F3 CF3C6H4OH

112.05 132.09 162.11

12, 717 61, 187

1.252 1.277 1.333

⬍1.30 1.415020 1.458820

⫺5.5 ⫺1.8

22 75–76 178–179

⫺30 ⫺7 73

CF3CH2OH CF3CH2O2CCF3

100.04 196.05

13, 1342 23, 427

1.384220 4 1.472518 4

1.290720 1.281218

⫺43.5 ⫺65.5

74 55

29 0

HCF3 CF3SO3H

70.01 150.07

1, 59 34, 34

1.52⫺100 1.69525

1.325025

⫺160 34

⫺84 162

none

75 mL aq; 500 mL alc v s aq; misc eth

(CF3SO2)2O

282.13

34, 35

1.677

1.321220

84

none

dec aq, alc

CF3C6H4NH2

161.13

12, 870

1.290

1.480020

5–6

187

85

C6H5CF3 CH3CO2C[CO2(CH2)5CH3][CH2CO2(CH2)5CH3]2 [CH3(CH2)5]3N C3H7CO2C[CO2(CH2)5CH3][CH2CO2(CH2)5CH3]2 [CH3(CH2)5]3SiCl

146.11 486.65

5, 290

1.188620 1.005

1.414520 1.447020

⫺29

102

12 ⬎110

269.52 514.71

4, 188

0.794 0.993

1.441520 1.448020

163–265

⬎110 ⬎110

0.87120 4

1.45620

2,2,2-Trifluoroethyl mesylate, m453 2-(Trifluoromethyl)aniline, a126 3-(Trifluoromethyl)aniline, a127 Trifluoromethylbenzene, t311

v s alc, eth; i aq

1555mm

m-Trifluoromethylphenol, t304 4,4,4-Trifluoro-1-(2-thienyl)-1,3-butanedione, t132 ␣,␣,␣-Trifluorotoluidines, a126 thru a128 Triglyme, b211

RIGHT

Triethylenediamine, d61 Triethylene glycol, e139 Triethylene glycol dimethyl ether, b211 O,O,O-Triethyl phosphorothioate, t298

319.12

⫺55

misc aq

DEAN 37261 (McGHP)

t300 t301

ROTATED

t279

t287

INTERACTIVE

No. t316 t317 t318 t319

t320 t321

1.332

t322 t323 t324 t325 t326 t327

t332 t333 t334

Beilstein reference

Density, g/mL

Refractive index

0.799 1.45

1.44820

Melting point,⬚C

Boiling point,⬚C

Flash point,⬚C

Solubility in 100 parts solvent

⬎110

Trihexylsilane 1,2,3-Trihydroxybenzene 1,3,5-Trihydroxybenzene 3,4,5-Trihydroxybenzoic acid

[CH3(CH2)5]3SiH C6H3(OH)3

284.60 126.11

44, 3915 6, 1071

C6H3(OH)3

126.11

6, 1092

218–221

1 aq; 10 alc; s eth

(HO)3C6H2CO2H

170.12

10, 470

258–265

1.1 aq; 17 alc; 1 eth; 20 acet; i bz, chl, PE

2,3,4-Trihydroxybenzophenone 1,2,6-Trihydroxyhexane Triisobutylaluminum Triisobutylamine Triisodecyl phosphite Triisopropanolamine Triisopropoxyborane 1,3,5-Triisopropylbenzene Triisopropyl orthoformate Triisopropyl phosphite Triisopropylsilane 3,4,5-Trimethoxybenzaldehyde 1,2,3-Trimethoxybenzene 1,2,4-Trimethoxybenzene 1,3,5-Trimethoxybenzene 3,4,5-Trimethoxybenzoic acid

(HO)3C6H2COC6H5

230.22

8, 417

140–142

HO(CH2)4CH(OH)CH2OH

134.18

133

1,4, 2784

1.109

1.476020

4, 643 4, 166

1.449420 1.423020 1.460020

161 309

59 aq; 77 alc; 62 eth

1785mm

79

1.376420 1.488020

8610mm 192–193 166 305.4 139–141 232–236

⫺18 57 235 152 10 86

[(CH3)2CHCH2]3Al [(CH3)2CHCH2]3N [(CH3)2CH(CH2)7O]3P [CH3CH(OH)CH2]3N [(CH3)2CHO]3B C6H3[CH(CH3)2]3

198.33 185.36 502.80 191.27 188.08 204.36

43, 762 1, 363 5, 458

0.786 0.766 0.884 0.999650 20 0.815 0.845

4–6

CH[OCH(CH3)2]3

190.29

23, 39

0.854

1.397020

6618mm

42

[(CH3)2CHO]3P [(CH3)2CH]3SiH (CH3O)3C6H2CHO

208.24 158.36 196.20

1, 363 43, 1851 8, 391

0.91420 4 0.773

1.411020 1.434420

67 37

73–75

6411mm 8635mm 16510mm

C6H3(OCH3)3

168.19

6, 1081

1.112

43–45

241

⬎110

C6H3(OCH3)3

168.19

6, 1088

1.126

247

⬎110

C6H3(OCH3)3

168.19

6, 1101

51–53

255

85

(CH3O)3C6H2CO2H

212.20

10, 481

168–171

22710mm

⬍0 48–52

1.533020

pyrophoric

v s aq

i aq(sl hyd)

v s alc, eth; s chl

INTERACTIVE

t335

Formula weight

ROTATED

t329 t330 t331

Formula

LEFT

t328

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

t337 t338 t339 t340 t341 t342 t343 t344 t345 t346

1.333

t347 t348 t349 t350

t352

230.65

10, 487

(CH3O)3C6H2CH2OH

198.22

6, 1159

(CH3O)3B [-OB(OCH3)-]3 CH3OCH2CH(OCH3)2

103.91 173.53 120.15

CH3OCH2CH2CH(OCH3)2

134.18

CH3OCH2CH2CH2Si(OCH3)3

164.28

(CH3O)3SiH H2N(CH2)3Si(OCH3)3

122.20 179.29

C6H5NH(CH2)3Si(OCH3)3

1.233 23 4

1.543920 20

⫺34 10

18518mm 22825mm

⬎110

67–68 130 5956mm

⫺13 10 23

13, 3183

0.920 1.195 0.932

1.3568 1.399620 1.392120

1, 820

0.942

1.400420

4617mm

40

0.932

1.390020

142

40

0.960 1.027

1.357920 1.424020

81 9215mm

⫺4 83

255.39

1.070

1.555020

310

⬎110

(CH3O)3Si(CH2)3NHCH2CH2NH2

224.36

1.019

1.445020

14615mm

⬎110

(CH3O)3Si(CH2)3O2CC(CH3)"CH2

248.35

1.04520 4

1.431020

190

92

(CH3O)3Si(CH2)3NHCONH2

222.32

1.150

1.460020

217–250

98

(CH3)3CCO2H [(CH3)3CCO]2O

102.13 186.25

2, 319 2, 320

0.889 0.918

1.409020

163–164 193

63 57

(CH3)3CCOCl

120.58

2, 320

0.979

1.412020

105–106

8

72.09

4, 643

0.75220

1.43212

125–126

⫺18

(CH3)3Al

1, 287

81–84

12, 274

Trimellitic anhydride, b32 Trimesic acid, b31 Trimesoyl chloride, b33 Trimethoxymethylsilane, m455 Trimethylacetaldehyde, d677

⫺115

33–35

15

Trimethylacetamide, d678 Trimethylacetic acid, d679 Trimethylacetic anhydride, d680 Trimethylacetyl chloride, d681

hyd aq; misc alc, eth

s alk; v sl s alc

ROTATED

Tri-(2-hydroxyethyl)amine, t266 1,2,6-Trihydroxyhexane, h63 1,2,3-Trihydroxypropane, g19 Triiodomethane, i33 Trimellitic acid, b30

(CH3O)3C6H2COCl

RIGHT

t351

3,4,5-Trimethoxybenzoyl chloride 3,4,5-Trimethoxybenzyl alcohol Trimethoxyborane Trimethoxyboroxine 1,1,2-Trimethoxyethane 1,1,3-Trimethoxypropane 1,1,3-Trimethoxypropylsilane Trimethoxysilane 3-(Trimethoxysilyl)propylamine N-[3-(Trimethylsilyl)propyl]aniline N1-[3-(Trimethoxysilyl)propyl]ethylenediamine 3-(Trimethoxysilyl)propyl methacrylate [3-(Trimethoxysilyl)propyl]urea Trimethylacetic acid Trimethylaceticanhydride Trimethylacetyl chloride Trimethylaluminum

DEAN 37261 (McGHP)

t336

INTERACTIVE

No.

Name

Formula

Formula weight

Beilstein reference

Density, g/mL

Refractive index

4, 43

0.656

1.36310

⫺25.4

176.1

48

i aq; s alc, eth

1.504820

⫺43.9

169

48

s alc, bz, eth

0.863720 4

1.499420

⫺44.7

165

44

misc alc, bz, eth

91, 429

1.261

1.521420

38–40

19412mm

⬎110

100.20 116.20

12, 121 12, 447

0.690120 4 0.838025 4

1.389020 1.423322

⫺24.9 15–17

80.9 130.5

⫺6

126.24

5, 42

0.786

1.433020

141–143

18

138.2

7, 65

0.918

1.472020

⫺8.1

215

80

152.19

74, 2032

1.491020

26–28

9411mm

96

149

⬎110

135.21 153.27

12, 1160

0.963 0.902

1.551020 1.471620

C6H3(CH3)3

120.20

5, 399

0.894420 4

1.513920

C6H3(CH3)3

120.20

5, 400

0.875620 4

C6H3(CH3)3

120.20

5, 406

C6H3(CO2CH3)3

252.22

(CH3)2CHC(CH3)3 (CH3)3CC(CH3)2OH C6H9(CH3)3

t363 t364 t365

t366 t367 t368 t369

210.28 142.16

3

19 , 1604

238.42

1.012

1.462020

1.088

20

1.4620

12–13

67

86

0.896

1.482020

13

21550mm

⬎110

682.4mm

46

210.37 (CH3)3CCH2CH(CH3)CH2CHO

142.24

2mm

s alc, eth misc alc, eth

1.2 aq

65–58 13, 2894

0.817

1.421520

INTERACTIVE

t370

OCNCH2CH2C(CH3)CH2C(CH3)CH2CNO

41 aq; misc alc; s bz, chl, eth

ROTATED

(CH3)3C6H2NH2

t361 t362

59.11

LEFT

2,4,6-Trimethylaniline 1,3,3-Trimethyl-6-azabicyclo[3.2.1]octane 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Trimethyl 1,2,4benzenetri-carboxylate 2,2,3-Trimethylbutane 2,3,3-Trimethyl-2butanol 1,2,4-Trimethylcyclohexane 3,5,5-Trimethylcyclohex-2-ene-1-one 2,6,6-Trimethyl-2cyclohexene-1,4dione Trimethyl-1,6-diisocyanatohexane 2,2,6-Trimethyl-4H1,3-dioxin-4-one 4,4⬘-Trimethylenebis(1-methylpiperidine) 4,4⬘-Trimethylenedipiperidine 3,5,5-Trimethylhexanal

t360

1.334

96 75

t355 t356

t359

Solubility in 100 parts solvent

233 194

(CH3)3N

t358

Flash point,⬚C ⫺7

Trimethylamine

⫺117

Boiling point,⬚C 2.9

t354

t357

Melting point,⬚C

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

t372

t374 t375

3,5,5-Trimethylhexane 3,5,5-Trimethyl-1hexanol 3,5,5-Trimethylhexanoyl chloride

(CH3)2CHCH2CH(CH3)CH(CH3)2 (CH3)3CCH2CH(CH3)CH2CH2OH (CH3)3CCH2CH(CH3)CH2COCl

Trimethylhydroquinone 1,3,3-Trimethyl-2norbornanol

(CH3)3C6H(OH)2

128.26 144.25

13, 1755

0.721820 0.823620 4

1.405120 1.430025

176.89

23, 834

0.930

1.436020

152.19

6, 931

154.25

6, 70

131 193–194

80

188–190

140

172–174 0.964120 4

3,5,5-Trimethylcyclohex-2-en-1-one, i93 1,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acid, c4 Trimethylene chlorobromine, b307 Trimethylene chlorohydrin, c231 Trimethylenediamine, p190

endo-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol, b245 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene, p175 1,7,7-Trimethylbicyclo[2.2.1]hepten-2-one, c3 Trimethyl borate, t338 Trimethylchlorosilane, c266 ␣,␣,4-Trimethyl-3-cyclohexene-1-methanol, t13

⫺128 ⬍ ⫺70

s alc, eth

s aq; v s alc, bz, eth

39–45

201

73

s alc, eth

DEAN 37261 (McGHP)

t370a t371

Trimethylene dibromide, d121 Trimethylene dimercaptan, p195 Trimethylene glycol, p192 Trimethylethylene, m166 Trimethylgermanium bromide, b437

1.335 t364

t365

t367

RIGHT

t356

ROTATED

t368

t369

t375

INTERACTIVE

No. t376 t377 t378 t379 t380 t381 t382 t383

1.336

t384 t385 t386 t387 t388

t391

t393 t394

Beilstein reference

Density, g/mL

Refractive index

152.24

7, 96

0.94818

1.463518

120.15 106.12

22, 128 2, 19

0.942825 4 0.967620 4

113.16 (CH3)3CCH(CH3)CH2CH3 (CH3)2CHCH2C(CH3)3 (CH3)2CH[CH(CH3)]2CHCH3 (CH3)2CHCH(OH)C(CH3)2CH2OH

114.23 114.23 114.23 146.22

11, 12, 13, 13,

(CH3)3CCH2C(CH3)"CH2

112.22

13, 849

(CH3)3C6H2OH (CH3)3C6H2OH (CH3)3C6H2OH (CH3)3C6H(NH2)2

136.19 136.19 136.19 152.23

6, 518 6, 518 131, 190

(CH3O)3P(O) (CH3O)3P

140.08 124.08

1, 286 1, 285

Trimethyl phosphonoacetate 1,2,4-Trimethylpiperazine 2,4,6-Trimethylpyridine

(CH3O)2P(O)CH2CO2CH3

C5H2N(CH3)3

121.18

N-(Trimethylsilyl)acetamide Trimethylsilyl acetate N-(Trimethylsilyl)imidazole

CH3CONHSi(CH3)3

131.25

CH3CO2Si(CH3)3

132.24 140.26

62 127 500 2225

Melting point,⬚C 5

Boiling point,⬚C

Flash point,⬚C

192–194

52

v s alc, eth

1.385925 1.379020

107–109 100.6

16 15

v s alc, eth

0.887

1.421320

112–113

12

0.716020 4 0.691920 4 0.719020 4 0.92855 15

1.403020 1.391520 1.404220 1.451315

⫺112.3 ⫺107.4 ⫺109.2 52–56

110 99.2 113–114 232

⬍21 ⫺12 5 113

0.715020 4

1.411220

⫺93

101–102

⫺6

92–95 62–64 71–74 88–91

230–231

⫺46 ⫺78

197 111–112

107 27

1180.85mm

⬎110

1.396720 1.408020

182.11

1.125

1.437020

128.22

0.85125 25

1.448025

⫺50

151746mm

25

⫺46

171

57

46–49

186

57

⫺32

108 9414mm

4 5

43, 1857

22 4

0.9166

0.882 0.956

1.4959

1.388020 1.475120

s eth; sl s alc s bz, chl, eth s alc, org solv 1.8 aq; 75 alc; 22 bz; 25 acet

220

1.19720 1.04620 4

20, 250

Solubility in 100 parts solvent

100 aq; s alc dec aq; misc alc, acet, bz, PE

s aq, alc, acet, bz 3.5 aq; misc eth; s alc, bz, chl

INTERACTIVE

t395 t396

CH3C(OCH3)3 HC(OCH3)3

Formula weight

ROTATED

t392

1,3,3-Trimethyl-2norbornanone Trimethyl orthoacetate Trimethyl orthoformate 2,4,4-Trimethyl-2oxazoline 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,4-Trimethylpentane 2,2,4-Trimethyl-1,3pentanediol 2,4,4-Trimethyl-1pentene 2,3,5-Trimethylphenol 2,3,6-Trimethylphenol 2,4,6-Trimethylphenol 2,4,6-Trimethyl-1,3phenylenediamine Trimethyl phosphate Trimethyl phosphite

Formula

LEFT

t389 t390

Name

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

158.28

0.890

1.415020

5120mm

32

CF3SO3Si(CH3)3

222.26

1.228

1.360020

7780mm

25

[(CH3)3S]I

204.07

[(CH3)3S(O)]I

220.07

t405 t406 t407

t398

t399 t400 t400a

215–220 sublime 169 dec

1.337

136.24

5, 164

0.866880

1.429680

(CH3)3SiCH"CH2 (O2N)3C6H2NH2 C6H3(NO2)3 C6H3(NO2)3

100.24 228.12 213.11 213.11

0.649 1.76214 1.7316 1.68820 4

1.392020

12, 763 5, 271 5, 271

2,4,6-Trinitrotoluene

(O2N)3C6H2CH3

227.13

5, 347

1.65420 4

Trioctylamine 1,3,5-Trioxane

[(CH3(CH2)7]3N

353.68 90.08

4, 196 19, 381

0.809 1.17065

67.5

152.5

188–190 61–62 122.5

55 explodes explodes explodes

80.1

explodes

60.2

365–367 115

1.448520

Trimethylsilyl cyanide, c331 (N-Trimethyl)silyldiethylamine, d404 (N-Trimethyl)silyldimethylamine, d726 Trimethylsilyl iodide, i56

⬍ ⫺34 s hot acet; sl s alc 5.5 alc; 7.1 eth; i aq 0.035 aq; 1.9 alc; 1.5 eth; 6.2 bz 1.5 alc; 4 eth; s bz, acet; 0.01 aq ⬎110 45

17.2 aq18; v s alc, bz, eth, EtOAc

Trimethylsilylnitrile, c331 2,4,6-Trinitrophenol, p174 Triolein, g23

RIGHT

Trimethylolpropane, e183 Trimethylolpropane triacrylate, e114 Trimethylolpropane trimethacrylate, e185 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane, c277

DEAN 37261 (McGHP)

H2C"C(CH3)CO2Si(CH3)3

t401 t402 t403 t404

Trimethylsilyl methacrylate Trimethylsilyl trifluoromethane sulfonate Trimethylsulfonium iodide Trimethylsulfoxonium iodide 1,7,7-Trimethyltricyclo[2.2.1.O2,6]heptane Trimethylvinylsilane 2,4,6-Trinitroaniline 1,2,4-Trinitrobenzene 1,3,5-Trinitrobenzene

t397

ROTATED

t376

t379

t392

t396

t400a

t407

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No. t408

Name

Formula

Formula weight

Beilstein reference

1.338

t409

4,7,10-Trioxa-1,13tridecanediamine Tripentaerythritol

t410 t411 t412 t413 t414 t415

Triphenylamine Triphenylantimony Triphenylarsine 1,3,5-Triphenylbenzene Triphenylborane Triphenylmethane

t416 t417

(C6H5)3COH (C6H5)3CBr

260.34 323.24

6, 713 5, 704

(C6H5)3CCl

278.78

t419

Triphenylmethanol Triphenylmethyl bromide Triphenylmethyl chloride Triphenyl phosphate

(C6H5O)3P(O)

t420

Triphenylphosphine

t421

Triphenylphosphine oxide Triphenyl phosphite Triphenylsilane Triphenyltin acetate Triphenyltin chloride Triphenyltin hydroxide Tripropoxyborane Tripropylaluminum Tripropylamine Tripropylene glycol

t418

Refractive index

1.005

1.464020

O[CH2CH2O(CH2)3NH2]2

220.31

(HOCH2)3CCH2OCH2C(CH2OH)2CH2OCH2C(CH2OH)3 (C6H5)3N (C6H5)3Sb (C6H5)3As (C6H5)3C6H3 (C6H5)3B (C6H5)3CH

372.41

245.33 353.07 306.24 306.41 242.13 244.34

12, 181 16, 891 16, 828 5, 737 162, 636 5, 698

0.77400 1.434325 1.222548 1.205

1.19904

Melting point,⬚C

Boiling point,⬚C 1484mm

Flash point,⬚C

Solubility in 100 parts solvent

⬎110

225 dec

125–127 52–54 60–62 172–174 145 92–94

347–348 377 23314mm 460 20315mm 360

160–163 152–154

360 23015mm

5, 700

110–112

23520mm

326.29

6, 179

50–52

24410mm

223

(C6H5)3P

262.29

16, 759

79–81

377

181

(C6H5)3P(O)

278.29

16, 783

(C6H5O)3P (C6H5)3SiH CH3CO2Sn(C6H5)3 (C6H5)3SnCl (C6H5)3SnOH (CH3CH2CH2O)3B (CH3CH2CH2)3Al (CH3CH2CH2)3N H(OCH2CH2CH2)3OH

310.29 260.41 409.06 385.46 367.02 188.08 156.25 143.27 192.26

6, 177 162, 605 164, 1606 16, 914 16, 914 12, 369 4, 643 4, 139

360 1522mm

218 76

1.613948

1.013499 4

1.07581 4

⬎110

v s bz, eth; sl s alc v s bz, eth; s alc v s bz; s abs alc, eth v s hot alc, eth; 49 chl; 7 bz; s PE v s alc, bz, eth; i aq

misc alc; s bz, acet, chl, eth; i aq v s eth; s bz, chl, HOAc; sl s alc; i aq

LEFT

156–158 1.184

22–24 42–44 124–126 108 dec 124–126

1.394820 1.416020 1.44225

⫺107 ⫺93.5

s alc, bz, chl, eth s eth; sl s alc, bz

24013.5mm 175–177 842mm 155–158 273

32 ⫺18 36 141

v s alc; misc eth s aq, alc, eth s aq

INTERACTIVE

0.857620 4 0.823 0.753 1.021

1.590320

ROTATED

t422 t423 t424 t425 t426 t427 t428 t429 t430

4,4, 1625

Density, g/mL

t432 t433 t434 t435 t436 t437 t438 t439 t440

1.339

t441

t442 t443 t444

t446

248.4

HO(CH2CH2CH2O)3CH3

206.29

14, 2475 2, 21 4, 256

0.932

1.43020

0.967

1.42825 20 4

⫺42

20

276

135

242.4

127

40mm

misc aq, alc, eth

HC(OCH2CH2CH3)3 (H2NCH2CH2)3N

190.28 146.24

(C4H9OCH2CH2O)3P(O)

398.48

(ClCH2CH2O)3P(O)

285.49

(ClCH2CH2O)3P

269.49

[C4H9CH(C2H5)CH2O]3P(O)

434.65

13, 1734

(HOCH2)3CNH2

121.14

4, 303

171–172

CH3C(CH2OH)3

120.15

1, 520

200–203

(HOCH2)3CNHCH2CO2H

179.17

Merck: 12, 9783

187

satd aq0 is 0.8M

(HOCH2)3CNO2

151.12

1, 520

214 pure 175 tech

220 aq; v s alc; sl s bz

(CH3OCH2CH2OCH2CH2)3N

323.43

H2C"CHSi(OCH2CH2 9OCH3)3

280.39

(CH3OCH2CH2O)3B [H2C"C(CH3)CH2]3N

12, 337

0.8805 0.977

1.4072 1.497020

108 11415mm

72 ⬎110

1.006

1.435920

2284mm

110

1.390

1.472120

330

232

1.35320 4

1.486320

1152mm

190

misc alc, bz, eth

0.924

1.443720

2154mm

⬎110

i aq

22010mm

⬎110

1.011

1.448620

44, 4257

1.03425 4

1.42725

284–286

⬎110

236.08

13, 2118

1.010

1.415020

13515mm

87

179.31

43, 462

0.794

1.457520

8515mm

53

Triphenyltin chloride, c267 Tripropyl borate, t427 TRIS, t439 Tris(dimethylamino)phosphine oxide, h50

Tris(dimethylamino)silyl chloride, c268a Tris(3,5-dioxaheptyl)amine, t443 Tris(7-methylnonyl) phosphite, t324 Tris(2-methylphenyl) phosphate, t452

ROTATED

Trioxymethylene, t407 Tripalmitin, g24 Triphenylmethyl bromide, b440 Triphenyl azide, a310

HO(CH2CH2CH2O)3(CH2)3CH3

RIGHT

t445

Tripropylene glycol butyl ether Tripropylene glycol monomethyl ether Tripropyl orthoformate Tris(2-aminoethyl)amine Tris(2-butoxyethyl) phosphate Tris(2-chloroethyl) phosphate Tris(2-chloroethyl) phosphite Tris(2-ethylhexyl) phosphate Tris(hydroxymethyl)aminomethane 1,1,1-Tris(hydroxymethyl)ethane N-[Tris(hydroxymethyl)methyl]glycine Tris(hydroxymethyl)nitromethane Tris[2-(2-methoxyethoxy)ethyl]amine Tris(2-methoxyethoxy)vinylsilane Tris(2-methoxyethyl) borate Tris(2-methylallyl)amine

DEAN 37261 (McGHP)

t431

INTERACTIVE

No. t447 t448

Name

Formula

Tris(2,2,2-trifluoroethyl) phosphite Tris[3-(trimethoxysilyl)propyl] isocyanurate Tris(trimethylsilyl) borate 1,3,5-Trithiane Trithiocarbonic acid Tri-o-tolyl phosphate

(CF3CH2O)3P

Formula weight 328.07

Beilstein reference 14, 1371

615.86

Density, g/mL

Refractive index

1.487

1.324520

131743mm

⬎110

1.170

1.461020

250

102

186

42

0.831

1.386120

(HS)2CS (CH3C6H4O)3P(O)

138.27 110.21 368.37

19, 382 3, 221 Merck: 12, 9893

1.48320 4 1.195520

1.822520 1.557520

(H2C"CH)3C6H9

162.28

0.836

1.478020

t454

1,2,4-Trivinylcyclohexane L-(⫺)-Tryptophan

t455

L-Tyrosine

u1 u2 u3 u4 u5 u6 u7 u8 u9 u10 u11 u12 u12a u13 u14

t450 t451 t452 t453

216–218 ⫺26.9 11

1.340

204.23

22, 546

(HO)C6H4CH2CH(NH2)CO2H

181.19

14, 605

1.456

Undecanal Undecane Undecanenitrile Undecanoic acid Undecanoic ␥-lactone Undecanoic ␦-lactone 1-Undecanol 2-Undecanol 2-Undecanone

CH3(CH2)9CHO CH3(CH2)9CH3 CH3(CH2)9CN CH3(CH2)9CO2H

1, 712 1, 170 2, 358 2, 358 17, 247 173, 4257 1, 427 1, 427 1, 173

0.825 0.740220 4 0.823 0.8907 0.949 0.969 0.8324 0.828 0.829

1.432220 1.417320 1.433020 1.429445 1.450020 1.459020 1.440220 1.437020 1.430020

⫺4 ⫺25.6

CH3(CH2)10OH CH3(CH2)8CH(OH)CH3 CH3(CH2)8COCH3

170.30 156.31 167.30 186.30 184.28 184.28 172.31 172.31 170.30

3-Undecanone 6-Undecanone 10-Undecenal 1-Undecene 10-Undecenoic acid 10-Undecen-1-ol

CH3(CH2)7COCH2CH3 CH3(CH2)4CO(CH2)4CH3 H2C"CH(CH2)8CHO H2C"CH(CH2)8CH3 H2C"CH(CH2)8CO2H H2C"CH(CH2)9OH

170.30 170.30 168.28 154.30 184.28 170.30

1, 713 1, 174 1,3, 3029 1, 225 2, 458 1, 452

0.827 0.831 0.810 0.750320 0.90724 4 0.85015

1.429120 1.428020 1.442720 1.426120 1.449320 1.450020

57.8 410

225

8820mm

68

280–285 dec 342–344

11 2–3 11–13

1155mm 196 253 228160mm 16613mm 15510.5mm 242.8 13128mm 231–232

96 60 ⬎110 ⬎110 ⬎110 ⬎110 ⬎110 88 88 (CC)

12–13 14.6

225–229 228

⫺49 24.5 ⫺2

193 1372mm 245

89 88 92 71 148 93

28.5

Solubility in 100 parts solvent

s bz; sl s alc, eth dec aq, alc; sl s eth sl s aq, alc; s eth

1.14 aq25; s hot alc, alk; i eth, chl 0.045 aq; 0.01 alc; s alk; i eth i aq; s alc, eth i aq; misc alc, eth s alc, chl, eth; i aq

s alc, bz, chl, eth, acet; i aq i aq; v s alc, eth

s alc, chl, eth; i aq

INTERACTIVE

43, 1861

Flash point,⬚C

ROTATED

278.38

Boiling point,⬚C

LEFT

[(CH3)3SiO]3B

t449

Melting point,⬚C

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

u16 u17 u18

10-Undecenoyl chloride Urea Uric acid Uridine

H2C"CH(CH2)8COCl

202.73

2, 459

0.944

(H2N)2CO

60.06 168.11 244.20

3, 42 26, 513 31, 23

1.335 1.89320

Trityl alcohol, t416 Triptamine, a170 Tyramine, a173 Umbelliferone, h111

1.454020

12210mm 133–135 ⬎300 dec 166–167

Undecyl alcohol, u7 Undecylenic aldehyde, u12 Undecyl-10-en-1-oic acid, u13 Undecylic aldehyde, u1

dec ⬎mp

93 100 aq; 20 alc s alk; i aq, alc, eth s aq; hot alc, pyr

Undecyl iodide, i57 Uracil, p278 4-Ureidohydantoin, a71 Urethane, e102

DEAN 37261 (McGHP)

u15

1.341 CH3(CH2)3CH2 t448

t450

t454

O

O

u5

RIGHT ROTATED

CH3(CH2)4CH3 u6

O

O u17

u18

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 1.15 Physical Constants of Organic Compounds (Continued)

No.

1.342

D-(⫹)-Xylose m-Xylylenediamine

(CH3)2CHCH(NH)CO2H H2C"CHO2CCH3 C6H5CO2CH"CH2 H2C"CHC6H4CH2Cl C6H11CH"CH2

HCONHCH"CH2

CH3CH2CO2CH"CH2 (C5H4N)CH"CH2 (C5H4N)CH"CH2

H2C"CHSi(OCH3)3

186.25 100.12 100.12 117.15 86.09 148.16 152.62 110.20 108.18 100.12 71.08 94.12 120.20 100.12 105.14 105.14 111.14

Beilstein reference 2, 301 17, 235 17, 235 4, 427 21, 63 91, 65 51, 35 51, 63

234, 569 23, 532 20, 256 202, 170

Density, g/mL

Refractive index

0.942 1.057 1.079 1.230 0.93220 4 1.070 1.083 0.805 0.80320 4 1.001 1.014 1.039 0.841 0.919 0.975 0.975 1.040

1.421020 1.433020 1.458020 1.395420 1.529020 1.574020 1.446320 1.464020 1.430020 1.494020 1.530820 1.480220 1.403020 1.549020 1.550020 1.512020

0.968

1.392020

148.24 182.22 226.23

17, 73 182, 279

C6H4(CH3)2 C6H4(CH3)2 C6H4(CH3)2 HOCH2(CHOH)3CH2OH

196.21 106.17 106.17 106.17 152.15

17, 354 5, 370 5, 362 5, 382 1, 531

0.864220 0.880820 4 0.861120 4 1.52

C6H4(CH2NH2)2

150.13 136.20

31, 47 13, 186

1.5350 1.032

Melting point,⬚C ⫺57 ⫺31 ⬎315 subl ⫺93

⫺101 ⫺16 ⫺80 ⫺80

101 217 dec

1.497220 1.505420 1.495820

1.570920

174–176 ⫺47.9 ⫺25.2 13 95–97 156–158 ⬎110

Boiling point,⬚C

Flash point,⬚C

11216mm 207–208 600.5mm

101 81 100

72–73 9620mm 229 126–127 127 115–116 210 7913mm 141 94–95 158–159 6515mm 9313mm

⫺8 82 104 20 20 14 102 81 27 6 46 51 93

123 310–312

22

350730mm 139 144–145 138

Solubility in 100 parts solvent

8.8 aq; v sl s alc, eth 2 aq; misc alc, eth

v s alc, chl, eth sl s hot aq, hot alc

s bz, eth; sl s alc, aq s hot alc, eth

27 32 27

0.5 alc; v s chl misc alc, eth; 0.02 aq misc alc, eth; 0.017 aq v s eth; s alc; 0.02 aq 64 aq; 1.2 EtOH; 6.0 MeOH 117 aq; s hot alc, pyr

INTERACTIVE

x8 x9

v18 x1 x2

[CH3(CH2)3CO]2O

Formula weight

ROTATED

x3 x4 x5 x6 x7

Valeric anhydride ␥-Valerolactone ␦-Valerolactone L-Valine Vinyl acetate Vinyl benzoate 4-Vinylbenzyl chloride Vinylcyclohexane 4-Vinyl-1-cyclohexene 2-Vinyl-1,3-dioxolane N-Vinylformamide 1-Vinylimidazole 5-Vinyl-2-norbornene Vinyl propionate 2-Vinylpyridine 4-Vinylpyridine N-Vinyl-2pyrrolidinone Vinyltrimethoxysilane Xanthene Xanthen-9-carboxylic acid 9-Xanthenone m-Xylene o-Xylene p-Xylene Xylitol

Formula

LEFT

v1 v2 v3 v4 v5 v6 v7 v8 v9 v10 v11 v12 v13 v14 v15 v16 v17

Name

1.343

v2

v9

x1

v10

x2

v12

x3

v13

x8

RIGHT

v17

v3

Vitamin B1, t135 Vitamin B2, r8 Vitamin C, a302 Xanthone, x3 Xylene-␣,␣⬘-diol, b18 Xylenols, d659 thru d664 Xylidenes, d554 thru d559 o-Xylyl bromide, b443 Xylyl chlorides, c271 thru c273 p-Xylylene glycol, b19

DEAN 37261 (McGHP)

Vinylacetic acid, b485 Vinylbenzene, s11 Vinyl bromide, b336 Vinyl butyl ether, b609 Vinyl chloride, c129 Vinyl cyanide, a63 Vinylethylene, b449 Vinylidene chloride, d227 Vinyltrimethylsilane, t401 Vinyltris(2-methoxyethoxy)silane, t444

Valeraldehyde, p28 Valeric acid, p38 Valeronitrile, p35 Valeryl chloride, p45 Vanillic acid, h143 Vanillin, h142 Vanillyl alcohol, h145 Veratraldehyde, d492 Veratric acid, d496 Veratrole, d493 Veronal, d330

ROTATED INTERACTIVE

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

top of page

SECTION 2

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS 2.1

GENERAL INFORMATION AND CONVERSION TABLES Table 2.1 Fundamental Physical Constants Table 2.2 Physical and Chemical Symbols and Definitions Table 2.3 Mathematical Symbols and Abbreviations Table 2.4 SI Prefixes Table 2.5 Greek Alphabet Table 2.6 Abbreviations and Standard Letter Symbols Table 2.7 Conversion Factors Table 2.8 Temperature Conversion Table 2.1.1 Conversion of Thermometer Scales 2.1.2 Density and Specific Gravity 2.1.3 Barometry and Barometric Corrections Table 2.9 Barometer Temperature Correction— Metric Units Table 2.10 Barometric Latitude-Gravity Table— Metric Units Table 2.11 Barometric Correction for Gravity— Metric Units Table 2.12 Reduction of the Barometer to Sea Level— Metric Units Table 2.13 Viscosity Conversion Table Table 2.14 Conversion of Weighings in Air to Weighings in Vacuo Table 2.15 Hydrometer Conversion Table Table 2.16 Pressure Conversion Chart Table 2.17 Corrections to Be Added to Molar Values to Convert to Molal Table 2.18 Molar Equivalent of One Liter of Gas at Various Temperatures and Pressures Table 2.19 Factors for Reducing Gas Volumes to Normal (Standard) Temperature and Pressure (760 mmHg) Table 2.20 Values of Absorbance for Percent Absorption Table 2.21 Transmittance-Absorbance Conversion Table Table 2.22 Wavenumber/Wavelength Conversion Table 2.2 MATHEMATICAL TABLES 2.2.1 Logarithms Table 2.23 Derivatives and Differentiation Table 2.24 Integrals 2.2.2 Surface Areas and Volumes 2.2.3 Trigonometric Functions of an Angle ␣ 2.2.4 Expansion in Series Table 2.25 Some Constants 2.3 STATISTICS IN CHEMICAL ANALYSIS 2.3.1 Introduction 2.3.2 Errors in Quantitative Analysis 2.3.3 Representation of Sets of Data 2.3.4 The Normal Distribution of Measurements Figure 2.10 The Normal Distribution Curve Table 2.26a Ordinates (Y) of the Normal Distribution Curve at Values of z Table 2.26b Areas Under the Normal Distribution Curve from 0 to z 2.3.5 Standard Deviation as a Measure of Dispersion 2.1

2.3 2.3 2.6 2.23 2.24 2.25 2.26 2.35 2.54 2.66 2.66 2.70 2.72 2.75 2.77 2.78 2.82 2.83 2.85 2.87 2.88 2.88 2.91 2.96 2.98 2.101 2.102 2.102 2.104 2.105 2.109 2.113 2.115 2.117 2.117 2.117 2.118 2.118 2.119 2.119 2.121 2.122 2.121

short standard base of DF

DEAN #37261

2.2

LEFT

(McGHP)

INTERACTIVE

top of rh base of rh

SECTION 2

2.3.6 Student’s Distribution or t Test Table 2.27 Percentile Values for Student t Distribution 2.3.7 Hypotheses About Means 2.3.8 The Chi-square (␹2) Distribution Table 2.28 Percentile Values for the Chi-square (␹2) Distribution 2.3.9 The F Statistic Table 2.29 F Distribution 2.3.10 Curve Fitting 2.3.11 Control Charts Bibliography

2.123 2.124 2.126 2.128 2.129 2.130 2.131 2.133 2.137 2.138

cap height base of text

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

2.1

2.3

cap height base of text

GENERAL INFORMATION AND CONVERSION TABLES

TABLE 2.1

top of rh base of rh

Fundamental Physical Constants

E. R. Cohen and B. N. Taylor, CODATA Bull. 63:1– 49 (1986); J. Res. Nat. Bur. Standards, 92:85 (1987). A. Defined values

Physical quantity 1. Base SI units Amount of substance

Name of SI unit

Symbol for SI unit

Definition

mole

mol

Amount of substance which contains as many specified entities as there are atoms of carbon-12 in exactly 0.012 kg of that nuclide. The elementary entities must be specified and may be atoms, molecules, ions, electrons, other particles, or specified groups of such particles.

Electric current

ampere

A

Magnitude of the current that, when flowing through each of two straight parallel conductors of infinite length, of negligible cross-section, separated by 1 meter in a vacuum, results in a force between the two wires of 2 ⫻ 10⫺7 newton per meter of length.

Length

meter

m

Distance light travels in a vacuum during 1/299 792 458 of a second.

Luminous intensity

candela

cd

Luminous intensity, in a given direction, of a source that emits monochromatic radiation of frequency 540 ⫻ 1012 hertz and that has a radiant intensity in that direction of 1/683 watt per steradian.

Mass

kilogram

kg

Mass of a cylinder of platinum-iridium alloy kept at Paris.

Temperature

kelvin

K

Defined as the fraction 1/273.16 of the thermodynamic temperature of the triple point of water.

Time

second

s

Duration of 9 192 631 770 periods of the radiation corresponding to the transition between the two hyperfine levels of the ground state of the cesium-133 atom.

radian

rad

The plane angle between two radii of a circle which cut off on the circumference an arc equal in length to the radius.

steradian

sr

The solid angle which, having its vertex in the center of a sphere, cuts off an area of the surface of the sphere equal to that of a square with sides of length equal to the radius of the sphere.

2. Supplementary SI units Plane angle

Solid angle

short standard long

DEAN #37261

LEFT

(McGHP)

2.4

INTERACTIVE

top of rh base of rh

SECTION 2

TABLE 2.1

cap height base of text

Fundamental Physical Constants (Continued) B. Derived SI units

Physical quantity Absorbed dose (of radiation) Activity (radioactive) Capacitance (electric) Charge (electric) Conductance (electric) Dose equivalent (radiation) Energy, work, heat Force Frequency Illuminance Inductance Luminous flux Magnetic flux Magnetic flux density Potential, electric (electromotive force) Power, radiant flux Pressure, stress Resistance, electric Temperature, Celsius

Name of SI unit

Symbol for SI unit

Expression in terms of SI base units

gray becquerel farad coulomb siemens sievert joule newton hertz lux henry lumen weber tesla volt

Gy Bq F C S Sv J N Hz lx H Lm Wb T V

J · kg⫺1 s⫺1 ⫽ m2 · s⫺2 C · V⫺1 ⫽ m⫺2 · kg⫺1 · s4 · A2 A·s ⍀⫺1 ⫽ m⫺2 · kg⫺1 · s3 · A2 J · kg⫺1 ⫽ m2 · s⫺2 N · m ⫽ m2 · kg · s⫺2 m · kg · s⫺2 s⫺1 cd · sr · m⫺2 V · A⫺1 · s ⫽ m2 · kg · s⫺2 · A⫺2 cd · sr V · s ⫽ m2 · kg · s⫺2 · A⫺1 V · s · m⫺2 ⫽ kg · s⫺2 · A⫺1 J · C⫺1 ⫽ m2 · kg · s⫺3 · A⫺1

watt pascal ohm degree Celsius

W Pa ⍀ ⬚C

J · s⫺1 ⫽ m2 · kg · s⫺3 N · m⫺2 ⫽ m⫺1 · kg · s⫺2 V · A⫺1 ⫽ m2 · kg · s⫺3 · A⫺2 ⬚C ⫽ (K ⫺ 273.15)

C. Recommended consistent values of constants Quantity

Symbol

Anomalous electron moment correction Atomic mass constant Avogadro constant Bohr magneton (⫽eh/4␲me) Bohr radius Boltzmann constant Charge-to-mass ratio for electron Compton wavelength of electron Compton wavelength of neutron Compton wavelength of proton Diamagnetic shielding factor, spherical water molecule Electron magnetic moment Electron radius (classical) Electron rest mass Elementary charge Energy equivalents: 1 electron mass 1 electronvolt

␮e ⫺ 1 mu ⫽ 1 u L, NA ␮B a0 k e/me ␭c ␭c,n ␭c,p 1 ⫹ ␴(H2O)

0.001 159 615(15) 1.660 540 2(10) ⫻ 10⫺27 kg 6.022 136 7(36) ⫻ 1023 mol⫺1 9.274 015 4(31) ⫻ 10⫺24 J · T⫺1 5.291 772 49(24) ⫻ 10⫺11 m 1.380 658(12) ⫻ 10⫺23 J · K⫺1 1.758 805(5) ⫻ 10⫺11 C · kg⫺1 2.426 309(4) ⫻ 10⫺12 m 1.319 591(2) ⫻ 10⫺15 m 1.321 410(2) ⫻ 10⫺15 m 1.000 025 64(7)

␮e re me e

9.284 770 1(31) ⫻ 10⫺24 J · T⫺1 2.817 938(7) ⫻ 10⫺15 m 9.109 389 7(54) ⫻ 10⫺31 kg 1.602 177 33(49) ⫻ 10⫺19 C

1 neutron mass 1 proton mass

1 eV/k 1 eV/hc 1 eV/h

Value*

0.511 003 4(14) MeV 1.160 450(36) ⫻ 104 K 8.065 479(21) ⫻ 103 cm⫺1 2.417 970(6) ⫻ 1014 Hz 939.573 1(27) MeV 938.279 6(27) MeV

* The digits in parentheses following a numerical value represent the standard deviation of that value in terms of the final listed digits.

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Fundamental Physical Constants (Continued) C. Recommended consistent values of constants (continued) Quantity

Symbol

1u Faraday constant Fine structure constant First radiation constant Gas constant g factor (Lande) for free electron Gravitational constant Hartree energy Josephson frequency-voltage ratio Magnetic flux quantum Magnetic moment of protons in water Molar volume, ideal gas, p ⫽ 1 bar, ␪ ⫽ 0⬚C Neutron rest mass Nuclear magneton Permeability of vacuum Permittivity of vacuum

Value* 931.501 6(26) MeV 96 485.309(29) C · mol⫺1 0.007 297 353 08(33) 137.035 989 5(61) 3.741 774 9(22) ⫻ 10⫺16 W · m2 8.314 510(70) J · K⫺1 · mol⫺1 2.002 319 304 386(20) 6.672 59(85) ⫻ 10⫺11 m3 · kg⫺1 · s⫺2 4.359 748 2(26) ⫻ 10⫺18 J 4.835 939(13) ⫻ 1014 Hz · V⫺1 2.067 851(5) ⫻ 10⫺15 Wb 1.520 993 129(17) ⫻ 10⫺3 22.711 08(19) L · mol⫺1

F ␣ ␣⫺1 c1 R ge G Eh ⌽0 ␮p/␮B

Planck constant Proton magnetic moment Proton magnetogyric ratio Proton resonance frequency per field in H2O Proton rest mass Quantum-charge ratio

mn ␮N ␮0 ⑀0 ប ⫽ h/2␲ h ␮p ␥p ␥⬘/2 p ␲ mp h/e

Quantum of circulation Ratio, electron-to-proton magnetic moments Rydberg constant Second radiation constant Speed of light in vacuum Standard acceleration of free fall Standard atmosphere Stefan-Boltzmann constant Thomson cross section Wien displacement constant Zeeman splitting constant

h/me ␮e/␮p R⬁ c2 c0 gn atm ␴ ␴e b ␮B/hc

1.674 928 6(10) ⫻ 10⫺27 kg 5.050 786 6(17) ⫻ 10⫺27 J · T⫺1 4␲ ⫻ 10⫺7 H · m⫺1 exactly 8.854 187 816 ⫻ 10⫺12 F · m⫺1 1.054 572 66(63) ⫻ 10⫺34 J · s 6.626 0.75 5(40) ⫻ 10⫺34 J · s 1.410 607 61(47) ⫻ 10⫺26 J · T⫺1 2.675 221 28(81) ⫻ 108 s⫺1 · T⫺1 42.576 375(13) MHz · T⫺1 1.672 623 1(10) ⫻ 10⫺27 kg 4.135 701(11) ⫻ 10⫺15 J · Hz⫺1 · C⫺1 7.273 89(1) ⫻ 10⫺4 J · s · kg⫺1 6.582 106 88(7) ⫻ 102 1.097 373 153 4(13) ⫻ 107 m⫺1 1.438 769(12) ⫻ 10⫺2 m · K 299 792 458 m · s⫺1 exactly 9.806 65 m · s⫺2 exactly 101 325 Pa exactly 5.670 51(19) ⫻ 10⫺8 W · m⫺2 · K⫺4 6.652 448(33) ⫻ 10⫺29 m2 0.289 78(4) cm · K 4.668 58(4) ⫻ 10⫺5 cm⫺1 · G⫺1

D. Units in use together with SI units Physical quantity Area Energy Length Mass

Name of unit barn electronvolt megaelectronvolt1 a˚ngstro¨m2 tonne

Symbol for unit b eV (e ⫻ V) MeV ˚ A t

Value in SI units 10⫺28 m ⬇1.60218 ⫻ 10⫺19 J 10⫺10 m; 0.1 nm 103 kg; Mg

*The digits in parentheses following a numerical value represent the standard deviation of that value in terms of the final listed digits. 1 The term million electronvolts is frequently used in place of megaelectronvolts. 2 The a˚ngstro¨m and bar are approved for temporary use with SI units; however, they should not be introduced if not used at present.

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Fundamental Physical Constants (Continued) D. Units in use together with SI units (continued)

Physical quantity

Name of unit unified atomic mass unit dalton3 degree minute second bar2 minute hour day liter (litre) milliliter

Plane angle

Pressure Time

Volume

Symbol for unit

Value in SI units

u[⫽ ma(12C)/12]

⬇1.66054 ⫻ 10⫺27 kg

Da ⬚ ⬘ ⬙ bar min h d L, l mL, ml

(␲/180) rad (␲/10 800) rad (␲/648 000) rad 105 Pa ⫽ 105 N m⫺2 60 s 3600 s 86 400 s dm3 ⫽ 10⫺3 m3 cm3 ⫽ 10⫺6 m3

2 The a˚ngstro¨m and bar are approved for temporary use with SI units; however, they should not be introduced if not used at present. 3 The name dalton and symbol Da have not been approved although they are often used for large molecules.

TABLE 2.2 Physical and Chemical Symbols and Definitions Symbols separated by commas represent equivalent recommendations. Symbols for physical and chemical quantities should be printed in italic type. Subscripts and superscripts which are themselves symbols for physical quantities should be italicized; all others should be in Roman type. Vectors and matrices should be printed in boldface italic type, e.g., B, b. Symbols for units should be printed in Roman type and should remain unaltered in the plural, and should not be followed by a full stop except at the end of a sentence. References: International Union of Pure and Applied Chemistry, Quantities, Units and Symbols in Physical Chemistry, Blackwell, Oxford, 1988; “Manual of Symbols and Terminology for Physicochemical Quantities and Units,” Pure Applied Chem. 31:577– 638 (1972), 37:499– 516 (1974), 46:71– 90 (1976), 51:1– 41, 1213– 1218 (1979); 53:753– 771 (1981), 54:1239– 1250 (1982), 55:931– 941 (1983); IUPAP-SUN, “Symbols, Units and Nomenclature in Physics,” Physica 93A: 1– 60 (1978). A. Atoms and molecules Name

Symbol

SI unit

Activity (radioactivity) Atomic mass constant Bohr magneton Bohr radius Decay (rate) constant Dissociation energy From ground state From the potential minimum Electric dipole moment of a molecule Electric field gradient

A mu ␮B a0 ␭ D, Ed D0 De p, ␮ q

Bq kg J · T⫺1 m s⫺1 J J J C·m V · m⫺2

Electric polarizability of a molecule Electron affinity Electron rest mass Elementary charge, proton charge Fine structure constant g factor

␣ Eea me e ␣ g

C · m2 · V⫺1 J kg C

Definition A ⫽ ⫺dNB/dt mu ⫽ ma(12C)/12 ␮B ⫽ eh/4␲me a0 ⫽ 2⑀0h2/mee2 A ⫽ ␭NB

Ep ⫽ ⫺p ⴢ E q␣␤ ⫽ ⫺⭸2V/⭸␣⭸␤ p(induced) ⫽ ␣E

␣ ⫽ e2/2⑀0hc

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) A. Atoms and molecules (continued) Name

Symbol

SI unit

Hartree energy Ionization energy Larmor circular frequency Larmor frequency Longitudinal relaxation time Magnetogyric ratio Magnetic dipole moment of a molecule Magnetizability of a molecule Mass of atom, atomic mass Neutron number Nuclear magneton Nucleon number, mass number Planck constant Planck constant/2␲ Principal quantum number (H atom) Proton number, atomic number Quadrupole interaction Quadrupole moment of a molecule

Eh Ei ␻L ␯L T1 ␥ m, ␮ ␰ m, ma N ␮N A h ប n Z ␹ Q; ⍜

J J s⫺1 Hz s C · kg⫺1 J · T⫺1 J · T⫺2 kg

J C · m2

Quadrupole moment Rydberg constant Transverse relaxation time

eQ R⬁ T2

C · m2 m⫺1 s

J · T⫺1 J·s J·s

Definition Eh ⫽ h2/4␲2mea20

␻L ⫽ (e/2m)B ␯L ⫽ ␻L /2␲ ␥ ⫽ ␮/L Ep ⫽ ⴚ m ⴢ B m⫽␰B N⫽A⫺Z ␮N ⫽ (me/mp)␮B ប ⫽ h/2␲ E ⫽ ⫺hcR/n2

␹␣␤ ⫽ eQq␣␤ Ep ⫽ 0.5 Q: V⬙ ⫽ 1⁄3 ⍜V ⬙ eQ ⫽ 2具⍜zz典 R⬁ ⫽ Eh/2hc

B. Chemical reactions Name Amount (of substance) Atomic mass Atomic mass constanta Avogadro constant Concentration, amount (concentration) Degree of dissociation Density (mass) Extent of reaction, advancement Mass (molecular or formula unit) Mass fraction Molality (of a solute) Molar mass Molar volume Molecular weight (relative molar mass) Mole fractionb, number fraction Number concentration Number of entities (e.g., molecules, atoms, ions, formula units) Pressure (partial) Pressure (total) Solubility

a b

Symbol

SI unit

Definition

n m, ma mu L, NA c ␣ ␳, ␥ ␰ m, mf w m M Vm Mr x, y C, n N

mol kg kg mol⫺1 mol · m⫺3

nB ⫽ NB/L

kg · m⫺3 mol kg

␳ ⫽ mB/V ⌬␰ ⫽ ⌬nB/␯BB

pB p, P s

Pa Pa mol · m⫺3

In biochemistry this unit is called the dalton, with symbol Da. For condensed phases x is used, and for gaseous mixtures y may be used.

mol · kg⫺1 kg · mol⫺1 m3 · mol⫺1

m⫺3

mu ⫽ ma(12C)/12 cB ⫽ nB/V

wB ⫽ mB/⌺mi mB ⫽ nB/mA MB ⫽ m/nB Vm,B ⫽ V/nB Mr,B ⫽ mB/mu xB ⫽ nB/⌺ni CB ⫽ NB/V pB ⫽ yBp sB ⫽ cB (saturated solution)

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) B. Chemical reactions (continued) Name

Symbol

␯ ⌫ ␾

Stoichiometric number Surface concentration Volume fraction Symbols for particles and nuclear reactions: ␣ Alpha particle Beta particle ␤⫺, ␤⫹ Deuteron d, 2H Electron e, e⫺ Helion h Muon, negative ␮⫺

Muon, positive Neutron Photon Proton Triton

SI unit

mol · m⫺2

⌫B ⫽ nB/A ␾B ⫽ VB/⌺Vi

␮⫹ n, n0 ␥ p, p⫹ t, 3H

The meaning of the symbolic expression indicating a nuclear reaction: initial incoming particles outgoing particles , nuclide or quanta or quanta

冉

Definition

冊

final nuclide

Examples: 14N(␣, p)17O, 23Na(␥, 3n)20Na States of aggregation: am amorphous solid aq aqueous solution as, ⬁ aqueous solution at infinite dilution g gas l liquid s solid sln solution

cd cr fl lc vit mon pol ads

condensed phase (solid or liquid) crystalline fluid phase (gas or liquid) liquid crystal vitreous substance monomeric form polymeric form species adsorbed on a substance

C. Chromatography Name

Symbol

Adjusted retention time Adjusted retention volume Average linear gas velocity Band variance Bed volume Capacity, volume Capacity, weight Column length Column temperature Column volume Concentration at peak maximum Concentration of solute in mobile phase Concentration of solute in stationary phase Density of liquid phase Diffusion coefficient, liquid film Diffusion coefficient, mobile phase

t⬘R V⬘R ␮ ␴2 Vg Qv Qw L ␪ Vcol Cmax CM

Definition t⬘R ⫽ tR ⫺ tM V⬘R ⫽ VR ⫺ VM ␮ ⫽ L/tM

Vcol ⫽ ␲Dd2c /4

CS

␳L Df DM

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) C. Chromatography (continued) Name Diffusion coefficient, stationary phase Distribution ratio

Symbol

Definition

DS Dc

⫽ [A⫹]S/[A⫹]M ⫽

amount of A per cm3 stationary phase amount of A per cm3 of mobile phase

Dg

⫽

amount A per gram dry stationary phase amount A per cm3 of mobile phase

Dv

⫽

amount A, stationary phase per cm3 bed volume amount A per cm3 of mobile phase

DS

⫽

amount of A per m2 of surface amount of A per cm3 of mobile phase

Elution volume, exclusion chromatography Flow rate, column Gas/liquid volume ratio Inner column volume Interstitial (outer) volume Kovats retention indices Matrix volume Net retention volume Obstruction factor Packing uniformity factor Particle diameter Partition coefficient Partition ratio Peak asymmetry factor Peak resolution Plate height Plate number Porosity, column Pressure, column inlet Presure, column outlet Pressure drop

Fc ␤ Vi Vo RI Vg VN ␥ ␭ dp K k⬘ AF Rs H Neff ⑀ pi Po ⌬P

Pressure-gradient correction

j

j⫽

Recovery factor Reduced column length Reduced plate height Reduced velocity Relative retention ratio Retardation factor c Retention time Retention volume Selectivity coefficient d Separation factor

Rn ␭ h v ␣ Rf tR VR kA,B ␣A/B

Rn ⫽ 1 ⫺ (rDc ⫹ 1)⫺n; r ⫽ Vorg/Vaq ␭ ⫽ L/dp h ⫽ H/dp v ⫽ ␮dp/DM ⫽ Kdp/tMDM ␣ ⫽ (k⬘/k⬘) 2 1 Rf ⫽ dsolute/dmobile phase tR ⫽ tM(1 ⫹ k⬘) ⫽ L/␮ VR ⫽ tRFc kA,B ⫽ [A⫹]r[B⫹]/[B⫹]r[A⫹] ␣A/B ⫽ (Dc)A/(Dc)B

c

Ve Fc ⫽ (␲d2c /4)(⑀tot)(L/tM)

VN ⫽ jV⬘R dp ⫽ L/Nh K ⫽ CS /CM ⫽ (VR ⫺ VM)/VS k⬘ ⫽ CSVS /CMVM ⫽ K(VS /VM) Ratio of peak half-widths at 10% peak height Rs ⫽ (tR,2 ⫺ tR,1)/0.5(W2 ⫹ W1) H ⫽ L/Neff Neff ⫽ L/H ⫽ 16(t⬘R /Wb)2 ⫽ 5.54(t⬘R /W1/2)2

3[(pi /po)2 ⫺ 1] 2[(pi /po)3 ⫺ 1]

The distance d corresponds to the movement of solute and mobile phase from the starting (sample spotting) line. Subscript “r” represents an ion-exchange resin phase. Two immiscible liquid phases might be represented similarly using subscripts “1” and “2.” d

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) C. Chromatography (continued) Name

Symbol

Specific retention volume Thickness (effective) of stationary phase Total bed volume Transit time of nonretained solute Vapor pressure Volume liquid phase in column Volume mobile phase in column Weight of liquid phase Zone width at baseline Zone width at 1⁄2 peak height

Definition V⬚g ⫽ 273 R/(p⬚ MwL)

V⬚g df Vtot tM, t0 p VL VM wL Wb W1/2

Wb ⫽ 4␴

D. Colloid and surface chemistry Name Adsorbed amount of B Area per molecule Area per molecule in a filled monolayer Average molar masses: Mass-average Number-average Z-average Contact angle Film tension Film thickness Reciprocal thickness of the double layer Retarded van der Waals constant Sedimentation coefficiente Specific surface area Surface coverage Surface excess of B Surface pressure Surface tension, interfacial tension Thickness of (surface or interfacial) layer Total surface excess concentration van der Waals constant van der Waals-Hamaker constant e

Symbol

SI unit

nsB a, ␴ am

mol m2 m2

Mm Mn MZ ␪ ⌺f t, h, ␦ ␬

kg · mol⫺1 kg · mol⫺1 kg · mol⫺1 rad N · m⫺1 ␾ m m⫺1

␤, B

J

s a, s, as ␪ n␴B ␲s, ␲ ␥, ␴

s m2/kg

␶, ␦, t

m

⌫

mol · m⫺2

␭ AH

J J

mol N · m⫺1 J · m⫺2

Definition

aB ⫽ A/N␴N am,B ⫽ A/Nm,B Mm ⫽ ⌺niM2i /⌺niMi Mn ⫽ ⌺niMi /⌺ni MZ ⫽ ⌺niM3i /⌺niM2i ⌺f ⫽ 2␥f

␬ ⫽ [2F2Ic/⑀RT]1/2

s ⫽ v/a a ⫽ A/m ␪ ⫽ N␴B/NB

␲s ⫽ ␥0 ⫺ ␥ ␥ ⫽ (⭸G/⭸As)T,p

⌫ ⫽ ⌺⌫i

v is the velocity of sedimentation and a is the acceleration of free fall or centrifugation.

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) E. Electricity and magnetism Name

Symbol

SI unit

Definition

Admittance Capacitance Charge density Conductance Conductivity Dielectric polarization (dipole moment per volume) Electrical resistance Electric current

Y C ␳ G ␬ P

S F, C · V⫺1 C · m ⫺3 S S · m ⫺1 C · m ⫺2

Y ⫽ 1/Z C ⫽ Q/U ␳ ⫽ Q/V G ⫽ 1/R ␬ ⫽ 1/␳ P ⫽ D ⫺ ⑀0E

R I

⍀ A

R ⫽ U/I ⫽ ⌬V/I I ⫽ dQ/dt

Electric current density

j, J

A · m⫺2

I⫽

Electric dipole moment Electric displacement Electric field strength

p, ␮ D E

C·m C · m ⫺2 V · m⫺1

p ⫽ Qr D ⫽ ⑀E E ⫽ F/Q ⫽ ⫺grad V

Electric flux

⌿

C

⌿⫽

Electric potential Electric potential difference Electric susceptibility

V, ␾ U, ⌬V ␹e

V, J · C⫺1 V

V ⫽ dW/dQ U ⫽ V2 ⫺ V1 ␹e ⫽ ⑀r ⫺ 1

Electromotive force

E

V

E⫽

Impedance Loss angle f Magnetic dipole moment Magnetic field strength

Z ␦ m, ␮ H

⍀ rad A · m2 A · m⫺1

Z ⫽ R ⫹ iX ␦ ⫽ (␲/2) ⫹ ␾I ⫺ ␾U Ep ⫽ ⫺mB B ⫽ ␮H

Magnetic flux

⌽

Wb

⌽⫽

Magnetization (magnetic dipole moment per volume) Magnetic susceptibility Magnetic vector potential Molar magnetic susceptibility Mutual inductance Permeability Permeability of vacuum Permittivity Permittivity of vacuum Poynting vector Quantity of electricity, electric charge Reactance Relative permeability Relative permittivityg Resistivity Self-inductance Susceptance

M

A · m⫺1

M ⫽ (B/␮0) ⫺ H

␹, ␬ A ␹m

Wb · m⫺1 n3/mol

␹ ⫽ ␮r ⫺ 1 B ⫽ ⵜA ␹m ⫽ Vm ␹

M, L12 ␮ ␮0 ⑀ ⑀0 S Q

H H · m⫺1 H · m⫺1 F · m ⫺1 F · m ⫺1 W · m⫺2 C

E1 ⫽ L12(dI2/dt) B ⫽ ␮H

X ␮r ⑀r ␳ L B

⍀

X ⫽ (U/I) sin ␦ ␮r ⫽ ␮/␮0 ⑀r ⫽ ⑀/⑀0 ␳ ⫽ E/j E ⫽ ⫺L(dI/dt) Y ⫽ G ⫹ iB

f g

⍀·m H S

␾I and ␾U are the phases of current and potential difference. This quantity was formerly called the dielectric constant.

冕

j dA

冕

冕

冕

D dA

(F/Q) ds

B dA

D ⫽ ⑀E ⑀0 ⫽ ␮0⫺1 c0⫺2 S⫽EⴢH

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) F. Electrochemistry Name

Symbol

SI unit

Definition

␴ z n, (z)

C · n⫺2

␴ ⫽ Q/A zB ⫽ QB/e

␬

S · m ⫺1

␬ ⫽ j/E

Kcell j kd

m⫺1 A · m⫺2 m · s⫺1

Kcell ⫽ ␬R j ⫽ I/A kd,B ⫽ |␯B|I1,B/nFcA

I ␮ ⌬V, E, U

A m2 · V⫺1 · s⫺1 V

I ⫽ dQ/dt ␮B ⫽ vB/E ⌬V ⫽ VR ⫺ VL

␮˜

J · mol⫺1

␮˜ ␣B ⫽ (⭸G/⭸n␣B)

Electrode reaction rate constant Electrokinetic potential (zeta potential) Elementary charge (proton charge) emf, electromotive force

k

(varies)

kox ⫽ Ia/ nFA

Charge density (surface) Charge number of an ion Charge number of electrochemical cell reaction Conductivity (specific conductance) Conductivity cell constant Current density (electric) Diffusion rate constant, mass transfer coefficient Electric current Electric mobility Electric potential difference (of a galvanic cell) Electrochemical potential

冉

兿c

冊

ni i

i

␨

V

e

C

E

V

E ⫽ lim ⌬V

emf of the cell Faraday constant Galvani potential difference Inner electrode potential Ionic conductivity Ionic strength Mean ionic activity Mean ionic activity coefficient Mean ionic mobility Molar conductivity (of an electrolyte)

E F ⌬␾ ␾ ␭ Ic, I a⫾ ␥⫾

V C · mol⫺1 V V S · m2 · mol⫺1 mol · m⫺3

E ⫽ E⬚ ⫺ (RT/nF) ⫻ ⌺␯i ln ai F ⫽ eL ⌬␤␣␾ ⫽ ␾␤ ⫺ ␾␣ ⵜ␾ ⫽ ⫺E ␭B ⫽ |zB|FuB Ic ⫽ 1⁄2⌺cizc2 a⫾ ⫽ m⫾␥⫾/m0 ␥ (⫾␯⫹ ⫹ ␯⫺) ⫽ (␥␯⫾⫹)(␥␯⫺⫺)

m⫾ ⌳

mol · kg⫺1 S · m⫺2 mol⫺1

m(⫾␯⫹ ⫹ ␯⫺) ⫽ (m␯⫹⫹)(m␯⫺⫺) ⌳B ⫽ ␬cB

pH

pH

Outer electrode potential Overpotential Reciprocal radius of ionic atmosphere Standard emf, standard potential of electrochemical cell reaction Surface electric potential Thickness diffusion layer

␺ ␩ ␬

V V m⫺1

␺ ⫽ Q/4␲⑀0r ␩ ⫽ EI ⫺ EI ⫽ 0 ⫺ IRu ␬ ⫽ (2F2I/⑀RT)1/2

E0

V

E0 ⫽ ⫺⌬rG0/nF ⫽ (RT/nF) ln K

␹ ␦

V m

␹⫽␾⫺␺ ␦B ⫽ DB/kd,B

Transfer coefficient

␣

Transport number Volta potential difference

t ⌬␺

I: 0

pH ⯝ ⫺log

␣c ⫽ V

冋

c(H⫹) mol · dm⫺3

册

⫺|␯|RT ⭸ln|Ic| nF ⭸E

tB ⫽ jB/⌺ji ⌬␤␣ ⫽ ␺␤ ⫺ ␤␣

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) G. Electromagnetic radiation (continued) Name

Symbol

Absorbance Absorbance (decaidic) Absorbance (napierian) Absorption coefficient: Linear (decaidic) Linear (napierian) Molar (decaidic) Molar (napierian) Absorption index Angle of optical rotation Circular frequency Complex refractive index Concentration, amount of substance Concentration, mass Einstein transition probabilities: Spontaneous emission Stimulated absorption Stimulated emission Emittance By blackbody First radiation constant Frequency Irradiance (radiant flux received)

␣ A B

SI unit

Definition

␣ ⫽ ⌽abs /⌽0 A ⫽ ⫺log(1 ⫺ ␣i ) B ⫽ ⫺ln(1 ⫺ ␣i ) a ⫽ A/l ␣ ⫽ B/l ⑀ ⫽ a/d ⫽ A/cl ␬ ⫽ ␣/c ⫽ B/cl k ⫽ ␣/4␲␯˜

a, K ␣ ⑀ ␬ k ␣ ␻ nˆ c

m⫺1 m⫺1 m2 · mol⫺1 m2 · mol⫺1

␥

kg · m3

Anm Bmn Bnm ⑀ Mbb c1 ␯ E, (I)

s⫺1 s · kg⫺1 s · kg⫺1

dNn /dt ⫽ ⫺Anm Nn dNn /dt ⫽ ␳␯˜ (␯˜nm)BmnNm dNn /dt ⫽ ␳v˜ (␯˜nm)BmnNm ⑀ ⫽ M/Mbb

W · m2 Hz W · m⫺2

c1 ⫽ 2␲hc20 ␯ ⫽ c/␭ E ⫽ d⌽/dA

Molar refraction

R, Rm

m3 · mol⫺1

R⫽

Path length (absorbing) Optical rotatory power Planck constant Planck constant/2␲ Radiant energy Radiant energy density Radiant exitance, emitted radiant flux Radiant intensity Radiant power, radiant energy per time Refractive index Reflectance Second radiation constant Spectral radiant energy density: In terms of frequency In terms of wavelength In terms of wavenumber

l [␣]␪␭ h ប Q, W ␳, w M

m rad J·s J·s J J · m⫺3 W · m⫺2

I ⌽, P

W · sr⫺1 W

I ⫽ d⌽/d⍀ ⌽ ⫽ dQ/dt

n ␳ c2

K·m

n ⫽ c0 /c ␳ ⫽ ⌽refl /⌽0 c2 ⫽ hc0 /k

␳␯ , w␯ ␳␭ , w ␭ ␳␯˜ , w␯˜

J · m⫺3 · Hz⫺1 J · m⫺4 J · m⫺2

␳␯ ⫽ d␳/d␯ ␳␭ ⫽ d␳/d␭ ␳␯˜ ⫽ d␳/d␯˜

rad s⫺1, rad · s⫺1

␻ ⫽ 2␲␯ nˆ ⫽ ␩ ⫹ ik

mol · m3

(n2 ⫺ 1) Vm (n2 ⫹ 2)

[␣]␪␭ ⫽ ␣/␥l ប ⫽ h/2␲

␳ ⫽ Q/V M ⫽ d⌽/dAsource

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) G. Electromagnetic radiation (continued) Name Speed of light: In a medium In vacuum Stefan-Boltzmann constant Transmittance Wavelength Wavenumber: In a medium In vacuum

Symbol

SI unit

c c0 ␴ ␶, T ␭

m · s⫺1 m · s⫺1 W · m⫺2 · K⫺4

␴ ␯˜

m⫺1 m⫺1

Definition

c ⫽ c0 /n Mbb ⫽ ␴T 4 ␶ ⫽ ⌽tr /⌽0

m

␴ ⫽ 1/␭ ␯˜ ⫽ ␯/c0 ⫽ 1/n␭

H. Kinetics Name Activation energy Boltzmann constant Collision cross section Collision diameter Collision frequency Collision frequency factor Collision number Half-life Overall order of reaction Partial order of reaction Pre-exponential factor Quantum yield, photochemical yield Rate of change of quantity X Rate of concentration change (chemical reaction) Rate constant, rate coefficient Rate of conversion change due to chemical reaction Rate of reaction (based on concentration) Relaxation time Standard enthalpy of activation Standard entropy of activation Standard Gibbs energy of activation Volume of activation

Symbol

SI unit

Definition Ea ⫽ RT 2 d ln k/dT

Ea , E k, k B ␴ d ZA zAB , zAA ZAB , ZAA t1/2 n nB A ␾

J · mol⫺1 J · K⫺1 m2 m s⫺1 m3 · mol⫺1 · s⫺1 m⫺3 · s⫺1 s

(mol⫺1 · m3)n⫺1 · s⬃1

c(t1/2 ) ⫽ c0 /2 n ⫽ ⌺nB v ⫽ k⌸cnBB k ⫽ A exp(⫺Ea /RT)

X˙

(varies)

X˙ ⫽ dX/dt

rB , vB

mol · m⫺3 · s⫺1

rB ⫽ dcB /dt

k

(mol⫺1 · m3)n⫺1 · s⫺1

v ⫽ k⌸cnBB

␨˙

mol · s⫺1

␨˙ ⫽ d␨ /dt

v

mol · m⫺3 · s⫺1

v ⫽ ␨ /V ⫽ ␯⫺B 1 dcB/dt

␶ ⌬H⫹⫹

s J · mol⫺1

␶ ⫽ 1/(k1 ⫹ k⫺1 )

⌬S⫹⫹

J · mol⫺1 · K⫺1

⌬G⫹⫹

J · mol⫺1

⌬ ⫹⫹V

m3 · mol⫺1

␴AB ⫽ ␲d2AB dAB ⫽ rA ⫹ rB zAB ⫽ ZAB /LcAcB

⌬ ⫹⫹V ⫽ ⫺RT (⭸ln k/⭸p)T

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) I. Mechanics Name Acoustic factors: Absorption Dissipation Reflection Transmission Angular momentum Bulk modulus, compression modulus Density, mass density Energy Fluidity, kinematic viscosity Force Friction coefficient Gravitational constant Hamilton function Kinematic viscosity Kinetic energy Lagrange function Linear strain, relative elongation Mass Modulus of elasticity, Young’s modulus Moment of inertia Momentum Normal stress

Symbol

SI unit

Definition

␣a ␦ ␳ ␶ L K

J·s Pa

␳ E ␾

kg · m⫺3 J m · kg⫺1 · s

␳ ⫽ m/V

F ␮, ( f ) G H ␯ Ek L ⑀, e

N

F ⫽ dp/dt ⫽ ma Ffrict ⫽ ␮ Fnorm F ⫽ Gm1 m2 /r2 H(q, p) ⫽ T(q, p) ⫹ V(q) ␯ ⫽ ␩ /␳ Ek ⫽ 1⁄2 mv2 L(q, q˙) ⫽ T(q, q˙) ⫺ V(q) ⑀ ⫽ ⌬l/l

m E

kg Pa

E ⫽ ␴/⑀

I, J p ␴

kg · m2 kg · m · s⫺1 Pa

I ⫽ ⌺m iri2 p ⫽ m␷ ␴ ⫽ F/A

Potential energy

Ep

J

Ep ⫽

Power Pressure Reduced mass Relative density Shear modulus Shear strain Shear stress Sound energy flux Specific volume Surface density Surface tension Torque, moment of a force Viscosity (dynamic) Volume (or bulk) strain Weight

P p, P ␮ d G ␥ ␶ P, Pa ␷ ␳A , ␳S ␥, ␴ T, (M) ␩, ␮ ␪ G, (W, P)

W Pa, N · m⫺2 kg

N

P ⫽ dW/dt p ⫽ F/A ␮ ⫽ m1 m2 /(m1 ⫹ m2 ) d ⫽ ␳/␲0 G ⫽ ␶/␥ ␥ ⫽ ⌬x/d ␶ ⫽ F/A P ⫽ dE/dt ␷ ⫽ V/␮ ⫽ 1/␳ ␳A ⫽ m/A ␥ ⫽ dW/dA TⴝrⴛF ␶ x,z ⫽ ␭(d␷x /dz) ␪ ⫽ ⌬V/V0 G⫽m·g

Work

W, w

J

W⫽

N · m2 · kg⫺2 J m2 · s⫺1 J J

Pa Pa W m3 · kg⫺1 kg · m⫺2 N · m⫺1, J · m⫺2 N·m Pa · s

␣a ⫽ 1 ⫺ ␳ ␦ ⫽ ␣a ⫺ ␶ ␳ ⫽ Pr /P0 ␶ ⫽ Ptr /P0 L⫽rⴛp K ⫽ ⫺V0(dp/dV)

␾ ⫽ 1/␩

冕

冕

⫺ F · ds

F ⴢ ds

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) J. Solid state Name Acceptor ionization energy Bragg angle Bloch function Burgers vector Charge density of electrons Circular wave vector: For particles (k) For phonons (q) Conductivity tensor Curie temperature Debye circular frequency Debye circular wavenumber Debye-Waller factor Density of states Density of vibrational modes (spectral) Diffusion coefficient Diffusion length Displacement vector of an ion Donor ionization energy Effective mass Equilibrium position vector of an ion Fermi energy Gap energy Gru¨neisen parameter Hall coefficient Lattice plane spacing Lattice vector Lorenz coefficient

Symbol

SI unit

Definition

Ea ␪ uk(r) b ␳

J rad m⫺3/2 m C · m⫺3

k, q

m⫺1

k ⫽ 2␲/␭

␴ik TC ␻D qD B, D NE N␻, g

S · m⫺1 K s⫺1 m⫺1

␴ ⫽ ␳⫺1

J⫺1 · m⫺3 s · m⫺3

NE ⫽ dN(E)/dE N␻ ⫽ dN(␻)/d␻

D L u

m2 · s⫺1 m m

dN/dt ⫽ ⫺DA dn/dx L ⫽ (D␶)1/2 u ⴝ R ⴚ R0

Ed m* R0

J kg m

EF Eg ␥, ⌫ AH , RH d R, R0 L

J

Madelung constant

␣

Mobility Mobility ratio Neel temperature Number density, number concentration Order parameters: Long range Short range Order of reflection Particle position vector: Electron Ion position Peltier coefficient Reciprocal lattice vector (circular)

␮ b TN n

m3 · C⫺1 m m V2 · K⫺2

n␭ ⫽ 2d sin ␪ ␺(r) ⫽ uk(r) exp(ik · r)

␳(r) ⫽ ⫺e␺*(r)␺(r)

␥ ⫽ ␣V/␬CV E ⴝ ␳ ⴢ j ⴙ RH(B ⴛ j) L ⫽ ␭/␴T Ecoul ⫽

m2 · V⫺1 · s⫺1

␣ NAz⫹z⫺e2 4␲⑀0R0

␮ ⫽ ␷drift /E b ⫽ ␮ n /␮ p

K m⫺3

s ␴ n r Rj ⌸ G

m m V m⫺1

G ⴢ R ⴝ 2␲ m

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) J. Solid state (continued) Name

Symbol

SI unit

Definition

Relaxation time Residual resistivity Resistivity tensor Temperature Thermal conductivity tensor Thermoelectric force Thomson coefficient Translation vectors for the reciprocal lattice (circular) Translation vectors for crystal lattice Work function

␶ ␳R ␳ ␪ ␭ E ␮ b1; b2; b3 a*; b*; c*

s m ⍀·m K W · m⫺1 · K⫺1 V V · K⫺1 m⫺1

␶ ⫽ 1/␷F

a1; a2; a3 a; b; c ⌽

m

R ⫽ n1a1 ⫹ n2a2 ⫹ n3a3

J

⌽ ⴝ E⬁ ⴚ EF

Eⴝ␳ⴢj Jq ⴝ ⴚ ␭ ⴢ grad T a i ⴢ bk ⫽ 2␲␦ik

K. Space and time Name Acceleration Angular velocity Area Breadth Cartesian space coordinates Circular frequency, angular frequency Diameter Distance Frequency Generalized coordinate Height Length Length of arc Path length Period Plane angle Position vector Radius Relaxation time, time constant Solid angle Speed Spherical polar coordinates Thickness Time Velocity Volume

Symbol

SI unit

a, (g) ␻ A, As , S b x, y, z ␻

m · s⫺2 rad · s⫺1, s⫺1 m2 m m rad · s⫺1, s⫺1

d d ␯, f q, q i h l s s T ␣, ␤, ␥, ␪, ␾ r r ␶, T

m m Hz (varies) m m m m s rad, l

␻, ⍀ ␷, u, w, c r, ␪, ␾ d, ␦ t ␷, u, w, c V, (␷)

sr, l m · s⫺1 m, l, l m s m·s m3

m m s

Definition a ⫽ d␷/dt ␻ ⫽ d␾/dt

␻ ⫽ 2␲␯

␯ ⫽ 1/T

T ⫽ t/N ␣ ⫽ s/r r ⫽ xi ⫹ yj ⫹ zk

␶ ⫽ |dt/d ln x| ⍀ ⫽ A/r2 ␷ ⫽ |␷ |

␷ ⫽ dr/dt

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) L. Spectroscopy Name Asymmetry parameter

Symbol

␬

Centrifugal distortion constants: A reduction ⌬ J ⌬ JK ⌬ K ␦J ␦K S reduction DJ DJK DK d1 d2 Degeneracy, statistical g, d, ␤ weight Electric dipole moment of a p, ␮ molecule Electron spin resonance (ESR), electron paramagnetic resonance (EPR): Hyperfine coupling constant: In liquids a, A In solids T g factor g Electronic term Te Harmonic vibration wave␻e; ␻r number Inertial defect ⌬ Interatomic distances: Equilibrium distance re Ground state distance r0 Substitution structure disrs tance Zero-point average disrz tance Longitudinal relaxation T1 time ␦ Nuclear magnetic resonance (NMR), chemical shift, ␦ scale Coupling constant, direct DAB (dipolar) Magnetogyric ratio ␥ Shielding constant ␴A Spin-spin coupling conJAB stant Principal moments of inerIA ; IB ; IC tia Rotational constants: In frequency A; B; C In wavenumber A˜; B˜; C˜ Rotational term F Spin orbit coupling constant A Total term T Transition dipole moment of a molecule

SI unit

M, R

Definition

␬⫽

2B ⫺ A ⫺ C A⫺C

m⫺1

C·m

E p ⫽ ⴚp ⴢ E

Hz Hz

ˆ hfs /h ⫽ aSˆ ⴢ I H ˆ hfs /h ⫽ Sˆ ⴢ T ⴢ I H h␯ ⫽ g␮ B B Te ⫽ Ee /hc

m⫺1 m⫺1 kg · m2

⌬ ⫽ IC ⫺ IA ⫺ IB

m m m m s

␦ ⫽ 106(␯ ⫺ ␯0 )/␯0 Hz

Hz

␥ ⫽ 2␲␮ /Ih BA ⫽ (1 ⫺ ␴A )B H/h ⫽ JAB IA · IB

kg · m2

IA ⱕ IB ⱕ IC

Hz m⫺1 m⫺1 m⫺1 m⫺1

A ⫽ h/8␲ 2IA A˜ ⫽ h/8␲ 2IA F ⫽ Erot /hc Ts.o. ⫽ A 具 L˜ · S˜ 典 T ⫽ Etot /hc

C·m

M⫽

C · kg⫺1

冕

␺ ⬘p␺ ⬙ d␶

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) L. Spectroscopy (continued) Name Transition frequency Transition wavenumber Transverse relaxation time Vibrational anharmonicity constant Vibrational coordinates: Internal coordinates Normal coordinates, dimensionless Mass adjusted Vibrational force constants: Diatomic Polyatomic Dimensionless normal coordinates Internal coordinates Symmetry coordinates Vibrational quantum numbers Vibrational term

Symbol

␯ ␯˜, (␯) T2 ␻e ␹ e; ␹ rs ; gtt⬘

SI unit

Definition

Hz m⫺1 s m⫺1

␯ ⫽ (E⬘ ⫺ E ⬙)/h ␯˜ ⫽ T⬘ ⫺ T ⬙

f, (k)

J · m⫺2

f ⫽ ⭸2V/⭸r2

␾rst . . . , krst . . . f ij Fij vr ; lt

m⫺1 (varies) (varies)

f ij ⫽ ⭸2V/⭸ri ⭸rj Fij ⫽ ⭸2V/⭸Si⭸Sj

G

m⫺1

G ⫽ Evib /hc

R i , ri , ␪ j , etc. qr Qr

Quantum number symbol Angular momentum types Electron orbital One electron only Electron orbital ⫹ spin Electron spin One electron only Internal vibrational: Spherical top Other Nuclear orbital (rotational) Nuclear spin Sum of J ⫹ I Sum of N ⫹ S Sum of R ⫹ L(⫹j)

Operator symbol Lˆ ˆl Lˆ ⴙ Sˆ Sˆ sˆ

Total

Z axis

L l

ML ml

S s

MS ms

l(l␨)

ˆl ˆj, ␲ˆ ˆ R Iˆ ˆ F Jˆ ˆ N

R I F J N

z axis ⌳ ␭ ⍀⫽⌳⫹⌺ ␴ ⌺ Kl l(l␨) KR, kR

MI MF MJ

K, k K, k

M. Thermodynamics Name

Symbol

SI unit

Definition

Absolute activity Activity (referenced to Henry’s law):

␭

␭ B ⫽ exp( ␮ B /RT)

Concentration basis

ac

a c,B ⫽ exp

冋

␮ B ⫺ ␮ B* RT

册

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) M. Thermodynamics (continued) Name

Symbol

SI unit

Definition

冋 冋 冋

册 册 册

Molality basis

am

a m,B ⫽ exp

␮ B ⫺ ␮ B* RT

Mole fraction basis

ax

a x,B ⫽ exp

␮ B ⫺ ␮ B* RT

a

a B ⫽ exp

␥c ␥m ␥x f

a c,B ⫽ ␥c,B cB /c0 a m,B ⫽ ␥m,B mB /m0 a x,B ⫽ ␥x,B xB f B ⫽ a B /xB

Activity (referenced to Raoult’s law) Activity coefficient (referenced to Henry’s law): Concentration basis Molality basis Mole fraction basis Activity coefficient (referenced to Raoult’s law) Affinity of reaction Celsius temperature Chemical potential Compressibility: Isentropic Isothermal Compressibility factor Cubic expansion coefficient Enthalpy Entropy Equilibrium constant Equilibrium constant: Concentration basis Molality basis Pressure basis Fugacity

␮ B ⫺ ␮ B* RT

A ␪, t ␮

J · mol⫺1 ⬚C J · mol⫺1

A ⫽ ⫺(⭸G/⭸␰)p,T ␪/⬚C ⫽ T/K ⫺ 273.15 ␮ B ⫽ (⭸G/⭸n B )T,p,n

␬S ␬T Z ␣, ␣ V , ␥ H S K 0, K

Pa⫺1 Pa⫺1

␬ S ⫽ ⫺(1/V)(⭸V/⭸p)S ␬ T ⫽ ⫺(1/V)(⭸V/⭸p)T Z ⫽ pVm /RT ␣ ⫽ (1/V)(⭸V/⭸T)p H ⫽ U ⫹ pV dS ⱖ dq/T K⬚ ⫽ exp(⫺⌬ r G⬚/RT)

Kc Km Kp f

K⫺1 J J · K⫺1 (mol · m⫺3)⌺␯ (mol · m⫺1)⌺␯ Pa⌺␯ Pa

K c ⫽ ⌸ c␯ K m ⫽ ⌸ m␯ K p ⫽ ⌸ p␯ f B ⫽ ␭ B lim (p B /␭ B )T p:0

Fugacity coefficient Gibbs energy Heat Heat capacity: At constant pressure At constant volume Helmholtz energy Internal energy Ionic strength: Concentration basis Molality basis Joule-Thomson coefficient Linear expansion coefficient Massieu function Molar quantity X Osmotic coefficient: Molality basis Mole fraction basis

␾ G q, Q

J J

␾ B ⫽ f B /p B G ⫽ H ⫺ TS

Cp CV A U

J · K⫺1 J · K⫺1 J

C p ⫽ (⭸H/⭸T)p C V ⫽ (⭸U/⭸T)V A ⫽ U ⫺ TS ⌬U ⫽ q ⫹ w

Ic, I Im, I ␮ , ␮ JT ␣1

mol · kg⫺3 mol · kg⫺1 K · Pa⫺1 K⫺1

I c ⫽ 1⁄2⌺m B zB2 I m ⫽ 1⁄2⌺m B z2B ␮ ⫽ (⭸T/⭸p) H ␣ 1 ⫽ (l/l)(⭸l/T)

J Xm

J · K⫺1 (varies)

J ⫽ ⫺A/T X m ⫽ X/n

␾m ␾x

␾ m ⫽ ( ␮ A* ⫺ ␮ A )/(RTMA ⌺m B ) ␾ x ⫽ ( ␮ A ⫺ ␮ A*)/(RT ln x A )

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) M. Thermodynamics (continued) Name

Symbol

SI unit

Definition

Osmotic pressure (ideal dilute solution) Partial molar quantity X Planck function Pressure coefficient Ratio of heat capacities Relative pressure coefficient Second virial coefficient Specific quantity X Standard chemical potential Standard partial molar enthalpy Standard partial molar entropy Standard reaction enthalpy Standard reaction entropy Standard reaction Gibbs energy Surface tension

⌸

Pa

⌸ ⫽ c B RT

XB Y ␤ ␥ ␣p

(varies) J · K⫺1 Pa · K⫺1

X ⫽ (⭸X/⭸n B )T,p,n Y ⫽ ⫺G/T ␤ ⫽ (⭸P/⭸T)V ␥ ⫽ C p /C V ␣ p ⫽ (1/p)(⭸p/⭸T)V

B x ␮0 H0

m3 · mol⫺1 (varies) J · mol⫺1 J · mol⫺1

pVm ⫽ RT(1 ⫹ B/Vm ⫹ · · ·) x ⫽ X/m

S0

J · mol⫺1 · K⫺1

S 0 ⫽ ⫺(⭸␮ 0/⭸T)

⌬rH0 ⌬rS0 ⌬rG0

J · mol⫺1 J · mol⫺1 · K⫺1 J · mol⫺1

⌬ r H 0 ⫽ ⌺␯H 0 ⌬ r S 0 ⫽ ⌺ ␯S 0 ⌬ r G 0 ⫽ ⌺␯␮ 0

␥, ␴

␥ ⫽ (⭸G/⭸A s )T,p

Thermodynamic temperature Work

T

J · m⫺2, N · m⫺1 K

w, W

J

K⫺1

H 0 ⫽ ␮ 0 ⫹ TS

Symbols used as subscripts to denote a chemical reaction or process: ads adsorption mix mixing of fluids at atomization r reaction in general c combustion reaction sol solution of solute in solvent dil dilution of a solution sub sublimation (solid to gas) f formation reaction trs transition (two phases) fus melting, fusion (solid to liquid) Recommended superscripts: ⫹ activated complex, transition state ⫹ E excess quantity id ideal

⬁ * ⬚

infinite solution pure substance standard

N. Transport properties Name Coefficient of heat transfer Diffusion coefficient Flux (of a quantity X) Heat flow rate Heat flux Mass flow rate Mass transfer coefficient Thermal conductance Thermal conductivity

Symbol h, (k, K) D JX , J ␾ Jq qm , m kd G ␭, k

SI unit W · m⫺2 · K⫺1 m2 · s⫺1 (varies) W W · m⫺2 kg · s⫺1 m · s⫺1 W · K⫺1 W · m⫺1 · K⫺1

Definition h ⫽ Jq /⌬T D ⫽ Jn /(dc/dl) JX ⫽ A⫺1 dX/dt ␾ ⫽ dq/dt Jq ⫽ ␾/A qm ⫽ dm/dt G ⫽ ␾/⌬T ␭ ⫽ Jq /(dT/dl)

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TABLE 2.2 Physical and Chemical Symbols and Definitions (Continued) N. Transport properties (continued) Name Thermal diffusivity Thermal resistance Volume flow rate Dimensionless quantities: Alfve´n number Cowling number Euler number Fourier number Fourier number for mass transfer in binary mixtures Froude number Grashof number Grashof number for mass transfer in binary mixtures Hartmann number Knudsen number Lewis number Mach number Magnetic Reynolds number Nusselt number Nusselt number for mass transfer in binary mixtures Pe´clet number Pe´clet number for mass transfer in binary mixtures Prandtl number Rayleigh number Reynolds number Schmidt number Sherwood number Stanton number Stanton number for mass transfer in binary mixtures Strouhal number Weber number

Symbol a R qv , V

SI unit m2 · s⫺1 K · W⫺1 m3 · s⫺1

Definition a ⫽ ␭ /␳c p R ⫽ 1/G qv ⫽ dV/dt

Al Co Eu Fo Fo*

Al ⫽ ␷ (␳␮ )1/2/B Co ⫽ B 2/␮␳␷ 2 Eu ⫽ ⌬p/␳␷ 2 Fo ⫽ at/l 2 Fo* ⫽ Dt/l 2

Fr Gr Gr*

Fr ⫽ ␷ /(lg)1/2 Gr ⫽ l 3 go ⌬T␳2/␩2 Gr* ⫽ l 3g (⭸␳/⭸x)T,p (⌬x ␲ /␩)

Ha Kn Le Ma Rm, Re m

Ha ⫽ Bl(␬ /␩ )1/2 Kn ⫽ ␭ /l Le ⫽ a/D Ma ⫽ ␷ /c Rm ⫽ ␷␮␬ l

Nu Nu*

Nu ⫽ hl/k Nu* ⫽ k d l/D

Pe Pe*

Pe ⫽ ␷ l/a Pe* ⫽ ␷ l/D

Pr Ra Re Sc Sh St St*

Pr ⫽ ␩ /␳a Ra ⫽ l 3 g␣ ⌬T␳/␩ a Re ⫽ ␳␷ l/␩ Sc ⫽ ␩ /␳D Sh ⫽ k d l/D St ⫽ h/␳␷ c p St* ⫽ k d /␷

Sr We

Sr ⫽ lf/␷ We ⫽ ␳␷ 2 l/␥

Symbols used in the definitions of dimensionless quantities: Acceleration of free fall g Area A Cubic expansion coefficient ␣ Density ␳ Frequency f Length l Mass m Mean free path ␭ Mole fraction x

Pressure Speed Speed of sound Surface tension Temperature Time Viscosity Volume

p ␷ c ␥ T t ␩ V

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TABLE 2.3 Mathematical Symbols and Abbreviations Symbol or abbreviation ⫹ ⫺ ⫾ ⫿ ⬅ ⫻, center dot ⫼ ⫽ ⬇ ⯝ ⬎ ⬍ ⬎⬎ ⬍⬍ ⱖ ⱕ ⬀, ⬃ : ⬁ |a| an n 1/n p a, a 1/2 p a, a 具a典, a¯

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Meaning Plus Minus Plus or minus Minus or plus Identically equal to Multiplied by (ab, a ⫻ b, a · b) Divided by (a/b, ab⫺1 ) Not equal to Approximately equal to Asymptotically equal to Greater than Less than Much greater than Much less than Greater than or equal to Less than or equal to Proportional to Tends to, approaches Infinity Magnitude of a nth power of a nth root of a Square root of a Mean value of a

n

兿 a , ⌸a

i⫽1

i

i

log a or log 10 a log a b ln b, log e b e ␲ i n! ⬔ ⬜ || a⬚ a⬘ a⬙ sin a cos a tan a cot a sec a cos a arcsin a, sin⫺1 a arccos a, cos⫺1 a arctan a, tan⫺1 a sinh a cosh a tanh a

Product of a i Common (or Briggsian) logarithm to the base 10 of a Logarithm to the base a of b Natural (Napierian) logarithm (to the base e) of b Base (2.718) of natural system of logarithms Pi (3.1416) Imaginary quantity, square root of minus one n factorial (n! ⫽ 1 · 2 · 3 · · · n) Angle Perpendicular to Parallel to a degrees (angle) a minutes (angle); a prime a seconds (angle); a double prime sine of a cosine of a tangent of a cotangent of a secant of a cosecant of a Inverse sine of a (angle whose sine is a) Inverse sine of a (angle whose cosine is a) Inverse tangent of a (angle whose tangent is a) Hyperbolic sine of a Hyperbolic cosine of a Hyperbolic tangent of a

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TABLE 2.3 Mathematical Symbols and Abbreviations (Continued) Symbol or abbreviation cotanh a P(x, y) P(r, ␪ ) f(x), F(x) ⌬x dy dy or f⬘(x) dx 2 dy or f ⬙(x) dx 2 ⭸z ⭸x ⭸ 2z ⭸x ⭸y

Meaning Hyperbolic cotangent of a Rectangular coordinate of point P Polar coordinate of point P Function of x Increment of x Total differential of y Derivative of y ⫽ f(x) with respect to x Second derivative of y ⫽ f(x) with respect to x Partial derivative of z with respect to x Second partial derivative of z with respect to x and y

冕 冕

Integral of

b

Integral between the limits a and b

a

lim f(x)

limit of f(x) as x tends to a

x:a n

冘

Summation of a i between the limits 1 and n

i⫽1

TABLE 2.4 SI Prefixes Submultiple

Prefix

Symbol

Multiple

Prefix

Symbol

10⫺1 10⫺2 10⫺3 10⫺6 10⫺9 10⫺12 10⫺15 10⫺18 10⫺21 10⫺24

deci centi milli micro nano pico femto atto zepto yocto

d c m ␮ n p f a z y

10 102 103 106 109 1012 1015 1018 1021 1024

deka hecto kilo mega giga tera peta exa zetta yotta

da h k M G T P E Z Y

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TABLE 2.4 SI Prefixes (Continued) Numerical (multiplying) prefixes Number

Prefix

Number

Prefix

Number

Prefix

0.5 1 l.5 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18

hemi mono sesqui di (bis)* tri (tris)* tetra (tetrakis)* penta hexa hepta octa nona deca undeca dodeca trideca tetradeca pentadeca hexadeca heptadeca octadeca

19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38

nonadeca icosa henicosa docosa tricosa tetracosa pentacosa hexacosa heptacosa octacosa nonacosa triaconta hentriaconta dotriaconta tritriaconta tetratriaconta pentatriaconta hexatriaconta heptatriaconta octatriaconta

39 40 41 42 43 44 45 46 47 48 49 50 60 70 80 90 100 110 120 130

nonatriaconta tetraconta hentetraconta dotetraconta tritetraconta tetratetraconta pentatetraconta hexatetraconta heptatetraconta octatetraconta nonatetraconta pentaconta hexaconta heptaconta octaconta nonaconta hecta decahecta icosahecta triacontahecta

* In the case of complex entities such as organic ligands (particularly if they are substituted) the multiplying prefixes bis-, tris-, tetrakis-, pentakis-, . . . are used, i.e., -kis is added starting from tetra-. The modified entity is often placed within parentheses to avoid ambiguity.

TABLE 2.5 Greek Alphabet

Capital

Lower case

Name

Capital

Lower case

Name

〈 〉 ⌫ ⌬ ⌭ ⌮ ⌯ ⍜ ⌱ ⌲ ⌳ ⌴

␣ ␤ ␥ ␦ ⑀ ␨ ␩ ␪ ␫ ␬ ␭ ␮

Alpha Beta Gamma Delta Epsilon Zeta Eta Theta Iota Kappa Lambda Mu

⌵ ⌶ ⌷ ⌸ ⌹ ⌺ ⌻ ⌼ ⌽ ⌾ ⌿ ⍀

␯ ␰ ␱ ␲ ␳ ␴ ␶ ␷ ␾ ␹ ␺ ␻

Nu Xi Omicron Pi Rho Sigma Tau Upsilon Phi Chi Psi Omega

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TABLE 2.6 Abbreviations and Standard Letter Symbols Abampere Absolute Absolute activity Absorbance (decaidic) Absorbance (napierian) Absorptance Absorption coefficient, linear decaidic Absorption coefficient, linear napierian Absorption coefficient, molar decaidic Absorption coefficient, molar napierian Absorption index Acceleration Acceleration due to gravity Acetyl Acoustic absorption factor Acoustic dissipation factor Acoustic reflection factor Acoustic transmission factor Activation energy Activity (referenced to Raoult’s law) Activity (referenced to Henry’s law): Concentration basis Molality basis Mole fraction basis Activity (radioactive) Activity coefficient (referenced to Raoult’s law) Activity coefficient (referenced to Henry’s law): Concentration basis Molality basis Mole fraction basis Adjusted retention time Adjusted retention volume Admittance Affinity of reaction Alcohol Alfve´n number Alkaline Alpha particle Alternating current Amorphous Amount concentration Amount of substance Ampere Amplification factor Angle of optical rotation Angstrom Angular dispersion

abamp abs ␭ A B ␣ a, K

␣ ␮, ⑀ ␬ k a g, gn Ac ␣a ␦ ␳ ␶ Ea a

ac am ax A f

␥c ␥m ␥x t⬘R V⬘R Y A alc Al alk ␣ ac am c n A ␮ ␣ ˚, A A d␪/d␭

Angular momentum Angular momentum terms Angular velocity Anhydrous Approximate (circa) Aqueous solution Aqueous solution at infinite dilution Are, unit of area Area Area per molecule Astronomical unit Asymmetry parameter Atmosphere, unit of pressure Atomic mass Atomic mass constant Atomic mass unit Atomic number Atomic percent Atomic weight Average Average linear gas velocity Avogadro constant Axial angular momentum Axial spin angular momentum Bandwidth (10%) of a spectral filter Band variance Bar, unit of pressure Barn, unit of area Barrel Base of natural logarithms Becquerel Bed volume Beta particle Bloch function Body-centered cubic Bohr Bohr magneton Bohr radius Boiling point Boltzmann constant Bragg angle Breadth British thermal unit Bulk modulus Bulk strain Burgers vector Butyl Calorie, unit of energy Calorie, international steam table Candela Capacitance

␲ j, J, l, L, N ␻ anhyd ca. aq aq, ⬁ a A, S a, ␴ AU ␬ atm ma mu amu Z at.% at. wt. av ␮ L, NA ␭, ⌳, ⍀ ␴, ⌺ ⌬␭0.1

␴2 bar b bbl e Bq Vg ␤ uk(r) bcc b ␮B a0 bp k, kB ␪ b Btu K ␪ b Bu cal cal IT cd C

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QV QW x, y, z t,␪ cgs

⌬, ␦ D, d ␳ n z CP

␮ ␦ ca. ␻ k q ␲ Cit h ␴ d Z z Z Vcol cf. nˆ k, K, m, M

␬S ␬T Z K ␭c ␭c,n ␭c,p c

␥ Cmax CM

Concentration of solute in stationary phase Condensed phase (solid or liquid) Conductance Conductivity Conductivity cell constant Conductivity tensor Contact angle Coordinate, position vector Coulomb Counts per minute Coupling constant, direct dipolar Critical density Critical temperature Cross section Crystalline Cubic Cubic expansion coefficient Curie Cycles per second Curie temperature Dalton (atomic mass unit) Day Debye, unit of electric dipole Debye circular frequency Debye circular wave-number Debye-Waller factor Decay constant (radioactive) Decibel Decompose Degeneracy, statistical weight Degree of dissociation Degrees Baume Degrees Celsius Degrees Fahrenheit Density (mass) Density, critical Density, relative Density of liquid phase Density of states Density of vibrational modes (spectral) Detect, determine (d) Determination Deuteron Diamagnetic shielding factor Diameter Dielectric polarization Differential thermal analysis Diffusion coefficient Diffusion coefficient, liquid film

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TABLE 2.6 Abbreviations and Standard Letter Symbols (Continued) Capacity, volume Capacity, weight Cartesian space coordinates Celsius temperature Centimeter-gram-second system Centrifugal distortion constants: A reduction S reduction Charge density of electrons Charge number of electrochemical reaction Charge number of an ion Chemically pure Chemical potential Chemical shift Circa (approximate) Circular frequency Circular wave vector: For particles For phonons Circumference divided by the diameter Citrate Coefficient of heat transfer Collision cross section Collision diameter Collision frequency Collision frequency factor Collision number Column volume Compare (confer) Complex refractive index Component of angular momentum Compressibility: Isentropic Isothermal Compression factor Compression modulus Compton wavelength of electron Compton wavelength of neutron Compton wavelength of proton Concentration (amount of substance) Concentration (mass) Concentration at peak maximum Concentration of solute in mobile phase

2.27

CS cd G ␥, ␬ Kcell ␴ik ␪ r C cpm, c/m DAB dc tc ␴ cr, cryst cub ␣, ␣v, ␥ Ci Hz Tc Da d D ␻D qD D, B ␭ dB dec d, g, ␤

␣ ⬚Be ⬚C ⬚F ␳, ␥ dc d ␳L NE, ␳ N␻ det(d) detn d 1⫹␴ d P DTA D Df

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TABLE 2.6 Abbreviations and Standard Letter Symbols (Continued) Diffusion coefficient, mobile phase Diffusion coefficient, stationary phase Diffusion current Diffusion length Diffusion rate constant, mass transfer coefficient Dilute Dirac delta function Direct current Direct dipolar coupling constant Disintegration energy Disintegrations per minute Displacement vector of an ion Dissociation energy From ground state From the potential minimum Distribution ratio Donor ionization energy Dropping mercury electrode Dyne, unit of force Einstein transition probabilities Spontaneous emission Stimulated absorption Stimulated emission Electric charge Electric current Electric current density Electric dipole moment of a molecule Electric displacement Electric field gradient Electric field strength Electric flux Electric mobility Electric polarizability of a molecule Electric potential Electric potential difference Electric susceptibility Electrical conductivity Electrical conductance Electrical resistance Electrochemical transfer coefficient Electrokinetic potential Electromagnetic unit Electromotive force Electron Electron affinity

DM DS id L kd dil ␦ dc DAB Q dpm u D, Ed D0 De D Ed dme dyn A, B Anm Bmn Bnm Q I j, J p, ␮ D q E ⌿ u, ␮ ␣ V, ␾ U, ⌬V ␹e ␴ G R ␣

␨ emu E, emf e⫺, e Eea

Electron magnetic moment Electron paramagnetic resonance Electron radius Electron rest mass Electron spin resonance Electronvolt Electrostatic unit Elementary charge Elution volume, exclusion chromatography Emittance By blackbody Energy Energy density Energy per electron hole pair of ion pair in detector Enthalpy Entropy Entropy unit Equilibrium constant Concentration basis Molality basis Pressure basis Equilibrium position vector of an ion Equivalent weight Erg, unit of energy Especially et alii (and others) et cetera (and so forth) Ethyl Ethylenediamine Ethylenediamine-N,N,N⬘,N⬘tetraacetic acid Euler number Exempli gratia (for example) Expansion coefficient Exponential Extent of reaction Fano factor Farad Faraday constant Fermi, unit of length Fermi energy Film tension Film thickness Fine structure constant Finite change First radiation constant Flow rate Flow rate, column chromatography Fluid phase (gas or liquid) Fluidity

␮e EPR re me ESR eV esu e Ve

⑀ Mbb E w, ␳ ⑀ H S e.u. K, K0 Kc Km Kp R0 equiv wt erg esp. et al. etc. Et en EDTA Eu e.g. ␣ exp ␰ F F F f EF ⌺f h, t ␣ ⌬ c1 q Fc fl ␾

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⌽F PF F, J f ft e.g. F k F Fo Fr fp f, v f, ␮ Fr f ␾ gal ⌬␾ ␥ ␥ Eg g R G g G grad gr g ⌶ Gr grav G Gy ␥, ⌫ t1/2 E1/2 AH, RH H ␻ Ha Eh q, Q C Cp Cv ␾ J ha h h

Helmholtz energy Henry Hertz Hexagonal Horsepower Hour Hygroscopic Hyperfine coupling constant Hyperfine coupling tensor ibidem (in the same place) id est (that is) Ignition Impedance Inch Indices of a family of crystallographic planes Indirect spin-spin coupling constant Inductance Inertial defect Infinitesimal change Infrared Inner column volume Inner electric potential Inner electrode potential Inorganic Inside diameter Insoluble Interatomic distances: Equilibrium distance Ground-state distance Substitution structure distance Zero-point average distance Internal energy Interstitial (outer) volume In the place cited (loco citato) In the same place In the work cited Ionic conductivity Ionic strength Concentration basis Molality basis Ionization energy Irradiance Joule Joule-Thomson coefficient Kelvin Kilocalorie Kilogram Kilogram-force Kilowatt-hour Kinematic viscosity

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TABLE 2.6 Abbreviations and Standard Letter Symbols (Continued) Fluorescent efficiency Fluorescent power Flux Focal length Foot For example (exempli gratia) Force Force constant (vibrational levels) Formal concentration Fourier number Franklin, unit of electric charge Freezing point Frequency Friction coefficient Froude number Fugacity Fugacity coefficient Gallon Galvani potential difference Gamma, unit of mass Gamma radiation Gap energy (solid state) Gas (physical state) Gas constant Gauss g factor Gibbs energy Grade Grain, unit of mass Gram Grand partition function Grashof number Gravimetric Gravitational constant Gray Gru¨neisen parameter Half-life Half-wave potential Hall coefficient Hamilton function Harmonic vibration wavenumber Hartmann number Hartree energy Heat Heat capacity At constant pressure At constant volume Heat flow rate Heat flux Hectare, unit of area Height Helion

2.29

A H Hz hex hp h hygr a, A T ibid. i.e. ign Z in hkl JAB L ⌬ ␦ ir Vi ␾ ␾ inorg i.d. insol re r0 rs rz U Vo loc. cit. ibid. op. cit. ␭, ⌳ I Ic Im Ei E J ␮, ␮ JT K kcal kg kgf kWh v, ␾

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TABLE 2.6 Abbreviations and Standard Letter Symbols (Continued) Kinetic energy Knudsen number Kovats retention indices Lagrange function Lambda, unit of volume Lande´ g-factor Larmor circular frequency Larmor frequency Lattice plane spacing Lattice vector Lattice vectors Length Length of arc Lewis number Light year Limit (mathematics) Linear expansion coefficient Linear reciprocal dispersion Linear strain Liquid Liquid crystal Liter loco citato (in the place cited) Logarithm, common Logarithm, base e Longitudinal relaxation time Lorenz coefficient Loss angle Lumen Luminous intensity Lux Mach number Madelung constant Magnetic dipole moment of a molecule Magnetic field strength Magnetic flux Magnetic flux density Magnetic moment of protons in water Magnetic quantum number Magnetic Reynolds number Magnetic susceptibility Magnetic vector potential Magnetizability Magnetization Magnetogyric ratio Mass Mass absorption coefficient Mass concentration Mass density Mass flow rate Mass fraction Massieu function

K, T, Ek Kn RI L ␭ g, ge ␻L vL d R, R0 a, b, c l, L s Le l.y. lim ␣1 D⫺1, d␭/dx e, ⑀ l, lq lc L, 1 loc. cit. log ln T1 L ␦ lm I lx Ma ␣ m, ␮ H ⌽ B ␮p/␮B Mj Rm ␬, ␹ A ␰ M ␥ m ␮/␳, ␮m ␥, ␳ ␳ qm w J

Mass number Mass of atom Mass transfer coefficient Matrix volume Maximum Maxwell, unit of magnetic flux Mean ionic activity Mean ionic activity coefficient Mean ionic mobility Melting point Metallic Metastable Metastable peaks Meter Methyl Micrometer Micron Mile Miller indices Milliequivalent Millimeters of mercury, unit of pressure Millimole Minimum Minute Mixture Mobility Mobility ratio Modulus of elasticity Molal Molality Molar Molar (decadic) absorption coefficient Molar ionic conductivity Molar magnetic susceptibility Molar mass Molar quantity X Molar refraction Molar volume Mole Mole fraction, condensed phase Gaseous mixtures Mole percent Molecular weight Moment of inertia Momentum Monoclinic Monomeric form Muon, negative Muon, positive

A m, ma kd Vg max Mx a⫾ ␥⫾ W⫾ mp met m m* m Me ␮m ␮ mi h, l, k meq mmHg mM min m, min mixt ␮ b E m b M, M ⑀

␭, ⌳ ␹m M Xm R, Rm Vm mol x y mol % mol wt I, J p mn mon ␮⫺ ␮⫹

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M, L B e ␬ TN VN ve n ␮N N mn N N ␴ NMR ␮N I A C n N NA Nu ␥ Oe ⍀ op. cit. f /number L ⫽ 0, 1, 2, 3, . . . S, P, D, F, . . . ⌳ ⫽ 0, 1, 2, . . . ⌺, ⌸, ⌬, . . . l ⫽ 0, 1, 2, 3, . . . s, p, d, f, . . . n n n s

␴ org o-rh ␾ ␾m ␾x ⌸ oz

Outer diameter Outer electric potential Overall order of reaction Overpotential Oxalate Oxidant Packing uniformity factor Page(s) Parsec, unit of length Partial molar quantity Partial order of reaction Particle diameter Particle position vector: Electron Ion position Partition coefficient Partition function Partition ratio Parts per billion, volume Parts per billion, weight Parts per million, volume Parts per million, weight Pascal Path length (absorbing) Peak asymmetry factor Peak resolution Pe´clet number Peltier coefficient Percent Period of time Permeability Permeability of vacuum Permittivity Permittivity of vacuum pH, expressed in activity Expressed in molarity Phenyl Phosphorescent efficiency Phosphorescent power Photochemical yield Photoluminescence power Photon Pion Planck constant Planck constant/2␲ Planck function Plane angle Plate height Plate number, effective Poise Polymeric form Porosity, column Positron Potential energy Pound

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TABLE 2.6 Abbreviations and Standard Letter Symbols (Continued) Mutual inductance Napierian absorbance Napierian base Napierian molar absorption coefficient Neel temperature Net retention volume Neutrino Neutron Neutron magnetic moment Neutron number Neutron rest mass Newton Normal concentration Normal stress Nuclear magnetic resonance Nuclear magneton Nuclear spin angular momentum Nucleon number Number concentration Number density Number of entities Numerical aperture Nusselt number Obstruction factor Oersted, unit of magnetic field Ohm opere citato (in the work cited) Optical speed Orbital angular momentum: Quantum number Series symbol Orbital angular momentum (molecules): Quantum number Symbol Orbital angular momenta of individual electrons Order of Bragg reflection Order of reaction Order of reflection Order parameters (solid state), long range Short range Organic Orthorhombic Osmotic coefficient Molality basis Mole fraction basis Osmotic pressure (ideal dilute solution) Ounce

2.31

o.d. ␺ n ␩ Ox ox ␭ p. (pp.) pc X nB dp r Rj K q, Q, z, Z, ⍀ k⬘ ng/mL ng/g ␮g/mL ␮/g Pa l AF Rs Pe ⌸ % T ␮ ␮0 ⑀ ⑀0 paH pH Ph, ␾ ⌽P PP ␾ P ␥ ␲ h ប Y ␣, ␤, ␥, ␪, ␾ H Neff P pol ⑀ ␤⫹ V, ⌽, EP lb

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TABLE 2.6 Abbreviations and Standard Letter Symbols (Continued) Pounds per square inch Powder Power Poynting vector Prandtl number Pressure (partial) Pressure (total) Pressure coefficient Pressure, column inlet Pressure, column outlet Pressure, critical Pressure drop Pressure-gradient correction Principal moments of inertia Principal quantum number Probability Probability density Product sign Propyl Proton Proton magnetic resonance Proton magnetrogyric ratio Proton number Proton rest mass Pyridine Quadrupole interaction energy tensor Quadrupole moment of a molecule Quantity of electricity, electric charge Quantum of energy Quantum yield Rad, unit of radiation dose Radian Radiant energy Radiant energy density Radiant energy flux Radiant exitance Radiant flux received Radiant intensity Radiant intensity at time t after termination of excitation Radiant power Radiant power incident on sample Radiofrequency Radius Rate of concentration change Rate constant Rate of reaction Ratio of heat capacities Reactance Reciprocal lattice

psi pwd p S Pr p p, P ␤ pi po pc ⌬P j IA; IB; IC n P P ⌸ Pr p pmr ␥p Z mp py ␹ Q, ⍜ Q hv ␾ rad rad Q, W ␳, w dQ/dt M E I I(t) ⌽ P0 rf r r k v ␥ X a*, b*, c*

Reciprocal lattice vector (circular) Vectors for Reciprocal radius of ionic atmosphere Reciprocal temperature parameter, 1/kT Reciprocal thickness of double layer Reduced column length Reduced mass Reduced plate height Reduced velocity Reductant Reference Reflectance Reflection plane Refractive index Relative permeability Relative permittivity (dielectric constant) Relative pressure coefficient Relative retention ratio Relaxation time Rem, unit of dose equivalent Residual resistivity (solid state) Resistivity tensor Retardation factor Retarded van der Waals constant Retention time Retention volume Revolutions per minute Reynolds number Rhombic Rhombohedral Roentgen Root-mean-square Rotational constants: In frequency In wavenumber Rotational term (spectroscopy) Rotation-reflection Rydberg, unit of energy Rydberg constant Saturated Saturated calomel electrode Schmidt number Second Second radiation constant Second virial coefficient Sedimentation coefficient Selectivity coefficient

G a*; b*, c* ␬

␤ ␬ ␭ ␮ h v red ref ␳ ␴ n ␮r ⑀r ␣p ␣ ␶ rem ␳R ␳ Rf B, ␤ tR VR rpm Re rh rh-hed R rms A, B, C A˜; B˜; C˜ F Sn Ry R, R⬁ satd SCE Sc s c2 B s k

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L ␣ G ␥ ␶ Sh ␴ ␴ S Sv S/N sl c, s ␻, ⍀ ⍀F(P,DF)

⍀A s sol soln, sln solv P, Pa d ads sp gr V0g s v, ␷ ⌬␭em ⌬␭ex ⌬␭m Q␭ , dQ/d␭

␳␯ , w␯ ␳␯ , w␯ ␳␯˜ , w␯˜ d␾/d␭ g u, w c c0 r, ␪, ␾ s, S T1

Spin orbit coupling constant Spin-spin coupling constant Spin-spin (or transverse) relaxation time Spin wavefunctions Square Standard Standard enthalpy of activation Standard enthalpy of formation Standard entropy Standard entropy of activation Standard Gibbs energy of activation Standard Gibbs energy of formation Standard heat capacity Standard hydrogen electrode Standard partial molar enthalpy Standard partial molar entropy Standard potential of electrochemical cell reaction Standard reaction enthalpy Standard reaction entropy Standard reaction Gibbs energy Standard temperature and pressure Stanton number Statistical weight Statistical weight of atomic states Stefan-Boltzmann constant Steradian Stoichiometric number Stokes Summation sign Surface charge density Surface concentration Surface coverage Surface density Surface electric potential Surface pressure Surface tension Susceptance Svedberg, unit of time Symmetrical Symmetry coordinate Symmetry number Tartrate Temperature

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TABLE 2.6 Abbreviations and Standard Letter Symbols (Continued) Self-inductance Separation factor Shear modulus Shear strain Shear stress Sherwood number Shielding constant (NMR) Short-range order parameter Siemens Sievert Signal-to-noise ratio Slightly Solid Solid angle Solid angle over which luminescence is measured (F, fluorescence; P, phosphorescence; DF, delayed fluorescence) Solid angle over which radiation is absorbed in cell Solubility Soluble Solution Solvent Sound energy flux Spacing between crystal diffracting planes Species adsorbed on a substance Specific gravity Specific retention volume Specific surface area Specific volume Spectral bandwidth of emission monochromator Spectral bandwidth of excitation monochromator Spectral bandwidth of monochromator Spectral radiant energy Spectral radiant energy density: In terms of frequency In terms of wavelength In terms of wavenumber Spectral radiant energy flux Spectroscopic splitting factor Speed Speed of light: In a medium In vacuum Spherical polar coordinates Spin angular momentum Spin-lattice relaxation time

2.33

A JAB T2

␣, ␤ sq std H⫹⫹ ⌬Hf 0 S0 ⌬S⫹⫹ ⌬G⫹⫹ ⌬Gf 0 Cp SHE H0 S0 E0 ⌬rH 0 ⌬rS 0 ⌬rG 0 STP St W, ␤, ␻ g

␴ sr v St ⌺ ␴ ⌫ ␪ ␳A, ␳S ␹ ␲ ␥, ␴ B Sv sym S s, ␴ Tart ␪, ⍜

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TABLE 2.6 Abbreviations and Standard Letter Symbols (Continued) Temperature, thermodynamic Temperature at boiling point Term value spectroscopy Tesla Tetragonal Thermal conductance Thermal conductivity Thermal diffusivity Thermal resistance Thermoelectric force Thickness of diffusion layer Thickness of layer Thickness (effective) of stationary phase Thickness of surface layer Thickness of various layers Thomson coefficient Thomson cross section Time Time interval, characteristic Tonne Torr (mm of mercury) Torque Total bed volume Total term (spectroscopy) Transconductance Transfer coefficient Transit time of nonretained solute Transition Transition dipole moment of a molecule Transition frequency Transition wavenumber Translation (circular) Translation vectors for crystal lattice Transmission factor Transmittance Transport number Transverse relaxation time Triclinic Trigonal Triton (tritium nucleus) Ultrahigh frequency Ultraviolet Unified atomic mass unit United States Pharmacopoeia Vacuum van der Waals constant Vapor pressure Velocity Versus

T Tb T T tetr G ␭, k a R E ␦ t df

␶ ␦ ␮, ␶ ␴e t T, ␶ t, ton Torr T Vtot T gm ␣ tM, t0 tr M, R v v˜ b1; b2; b3 a 1; a 2; a 3 a; b; c ␶ T, ␶ t T2 tric trig t uhf uv u USP vac ␭ p, vp u, w vs

Vibrational anharmonicity constant Vibrational coordinates: Internal coordinates Normal coordinates, dimensionless Mass adjusted Vibrational force constants: Diatomic Polyatomic, dimensionless normal coordinates Internal coordinates Symmetry coordinates Vibrational quantum number Vibrational term Viscosity Vitreous substance Volt Volt-ampere-reactive Volta potential difference Volume Volume flow rate Volume fraction Volume in space phase Volume liquid phase in column Volume mobile phase in column Volume of activation Volume percent Volume per volume Volume strain Watt Wavefunction Wavelength Wavenumber (in a medium) Wavenumber in vacuum Weber Weber number Weight Weight of liquid phase Weight percent Weight per volume Wien displacement constant Work Work function x unit Yard Young’s modulus Zeeman splitting constant Zone width at baseline Zone width at one-half peak height

␹ Ri, rI, ␪j, etc. qr Qr f ␾rst

. . .

; krst

. . .

f ij Fij v G ␩, ␮ vit V var ⌬␺ V, v qv ␾ ⍀ VL VM ⌬⫹⫹V vol % v/v ␪ W ␾, ␺, ⌿ ␭ ␴ v˜ Wb We W wL wt % w/v b w, W ⌽ X yd E ␮B/hc Wb W1/2

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GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

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TABLE 2.7 Conversion Factors The data were compiled by L. P. Buseth for the 13th edition; some entries have been added or modified in view of recent data and SI units. Relations which are exact are indicated by an asterisk (*). Factors in parentheses are also exact. Other factors are within ⫾5 in the last significant figure. To convert Abampere Abcoulomb Abfarad Abhenry Abmho Abvolt Acre

Acre (U.S. survey) Acre-foot

Acre-inch Ampere per square centimeter Ampere-hour Ampere-turn Ampere-turn per centimeter ˚ ngstro¨m A Apostilb Are Assay ton Astronomical unit Atmosphere

Atomic mass unit Avogadro number

Into ampere* coulomb* statcoulomb farad* henry* siemens* volt hectare or square hectometer square chain (Gunter’s)* square kilometer* square meter* square mile* square rod* square yard* square meter cubic foot* cubic meter gallon (U.S.) cubic foot* cubic meter ampere per square inch* coulomb* faraday gilbert ampere-turn per inch meter* nanometer* candela per square meter lambert* acre square meter* gram meter light-year bar* foot of water (at 4⬚C) inch of mercury (at 0⬚C) kilogram per square centimeter millimeter of mercury* millimeter of water (4⬚C) newton per square meter* pascal* pound per square inch ton per square inch torr* gram molecules per mole

Multiply by 10 10 2.998 ⫻ 1010 109 10⫺9 109 10⫺8 0.404 685 64 10 0.004 046 873 4046.873 (1/640) 160 4840 4046.873 4.3560 ⫻ 104 1233.482 3.259 ⫻ 105 3630 102.7902 6.4516 3600 0.037 31 1.256 637 2.540 10⫺10 0.1 0.318 309 9; (1/␲) 10⫺4 0.024 710 54 100 29.1667 1.496 00 ⫻ 10⫺11 1.581 284 ⫻ 10⫺5 1.013 25.0 33.898 54 29.921 26 1.033 227 760 1.033 227 ⫻ 104 1.013 250 ⫻ 105 101 325.0 14.695 95 0.007 348 760 1.6605 ⫻ 10⫺24 6.022 137 ⫻ 1023

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TABLE 2.7 Conversion Factors (Continued) To convert Bar

Barn Barrel (British) Barrel (petroleum)

Barrel (U.S. dry)

Barrel (U.S. liquid) Barye Becquerel Biot Board foot Bohr Bohr magneton Bolt (U.S. cloth) Boltzmann constant British thermal unit (Btu)

Btu per foot3 Btu (International table)/ft3 Btu (thermochemical)/ft3 Btu (International table)/hour Btu (thermochemical)/hour Btu (International table)/pound Btu (thermochemical)/pound Btu (thermochemical)/(ft2 · h) Btu (thermochemical)/minute Btu (thermochemical)/pound Btu per square foot Bucket (British, dry)

Into atmosphere dyne per square centimeter* kilogram per square centimeter millimeter of mercury millimeter of water (4⬚C) newton per square meter pascal* pound per square inch square meter* gallon (British)* liter gallon (British) gallon (U.S.)* liter bushel (U.S.) cubic foot liter quart (U.S. dry) gallon (U.S.) liter dyne per square centimeter* curie* ampere* cubic foot cubic meter meter joule per tesla foot* meter joule per degree calorie cubic foot-atmosphere erg foot-pound horsepower-hour (British) horsepower-hour (metric) joule (International table) joule (thermochemical) kilogram-calorie kilogram-meter kilowatt-hour liter-atmosphere kilocalorie per cubic meter joule per meter3 joule per meter3 watt watt joule per kilogram* joule per kilogram watt per meter2 watt joule per kilogram joule per square meter gallon (British)*

Multiply by 0.986 923 106 1.019 716 750.062 1.019 716 ⫻ 104 105 105 14.503 77 10⫺28 36 163.659 34.9723 42 158.987 3.281 22 4.083 33 115.6271 104.9990 31.5 (variable) 119.2405 1 2.7 ⫻ 10⫺11 10 (1/12) 2.359 737 ⫻ 10⫺3 5.291 77 ⫻ 10⫺11 9.274 02 ⫻ 10⫺24 120 36.576 1.3806 ⫻ 10⫺23 251.996 0.367 717 1.0550 ⫻ 1010 778.169 3.930 15 ⫻ 10⫺4 3.984 66 ⫻ 10⫺4 1055.056 1054.350 0.2520 107.5 2.930 71 ⫻ 10⫺4 10.4126 8.899 15 3.725 895 ⫻ 104 3.723 402 ⫻ 104 0.293 071 1 0.292 875 1 2.326 ⫻ 103 2.324 444 ⫻ 103 3.154 591 17.572 50 2.324 444 ⫻ 103 1.135 65 ⫻ 104 4

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TABLE 2.7 Conversion Factors (Continued) To convert Bushel (British)

Bushel (U.S.)

Cable length (international)

Cable length (U.S. or British)

Caliber Calorie

Calorie (15⬚C) Calorie (international) Calorie per minute

Candela Candela per square centimeter

Carat (metric) Celsius temperature Centigrade heat unit or chu

Centimeter

Centimeter of mercury (0⬚C) Centimeter of water (4⬚C) Centimeter per second

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Into bushel (U.S.) cubic foot gallon (British)* gallon (U.S.) liter barrel (U.S., dry) bushel (British) cubic foot cubic meter gallon (British) gallon (U.S.) liter peck (U.S.)* pint (U.S., dry)* foot meter* mile (nautical)* foot* meter mile (nautical) mile (statute) inch* millimeter* Btu foot-pound foot-poundal horsepower-hour (British) joule* kilowatt-hour liter-atmosphere joule joule foot-pound per second horsepower (British) watt* Hefner unit lumen per steradian* candela per square foot* candela per square meter* lambert gram* Fahrenheit temperature kelvin Btu* calorie joule foot inch mil pascal pascal foot per minute kilometer per hour*

Multiply by 1.032 057 1.284 35 8 9.607 60 36.3687 0.304 765 0.968 939 1.244 456 0.035 239 07 7.751 51 9.309 18 35.239 07 4 64 607.611 55 185.2 0.1 720 219.456 0.118 407 0.136 364 0.01 0.254 0.003 968 320 3.088 03 99.3543 1.559 61 ⫻ 10⫺6 4.184 1.163 ⫻ 10⫺6 0.041 320 5 4.1858 4.1868 0.051 467 1 9.357 65 ⫻ 10⫺5 0.069 78 1.11 1 929.0304 104 3.141 593; (␲) 0.2 (9/5)⬚C ⫹ 32 ⬚C ⫺ 273.15 1.8 453.592 1899.10 0.032 808 4 0.393 700 8 393.700 8 1333.22 98.063 8 1.986 50 0.036

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TABLE 2.7 Conversion Factors (Continued) To convert Centimeter per second (continued) Centimeter per second squared Centimeter-dyne

Centimeter-gram Centipoise

Chain (Ramsden’s) Chain (Gunter’s) Circular inch

Circular millimeter Circumference

Cord Coulomb Coulomb per square centimeter Cubic centimeter

Cubic centimeter-atmosphere Cubic centimeter per gram Cubic centimeter per second Cubic decimeter (dm3 ) Cubic foot

Into knot mile per hour foot per second squared meter per second squared* erg* joule* meter-kilogram pound-foot erg* joule* kilogram per (meter-second)* pascal-second* pound per (foot-second) foot* meter* foot* meter* circular mil* square centimeter square inch square millimeter degree* gon (grade) radian cord foot* cubic foot* ampere-second* coulomb per square inch* cubic foot cubic inch dram (U.S., fluid) gallon (British) gallon (U.S.) liter* minim (U.S.) ounce (British, fluid) ounce (U.S., fluid) pint (British) pint (U.S., dry) pint (U.S., liquid) joule* watt-hour cubic foot per pound cubic foot per minute liter per hour* liter* acre-foot board foot* cord* cord foot* cubic inch* cubic meter* cubic yard

Multiply by 0.019 438 4 0.022 369 4 0.032 808 4 0.01 1 10⫺7 1.020 ⫻ 10⫺8 7.376 ⫻ 10⫺8 980.665 9.806 65 ⫻ 10⫺5 0.001 0.001 0.006 72 100 30.48 66 20.1168 106 5.067 075 (␲/4) (␲/4) 360 400 (2␲) 8 128 1 6.4516 3.531 47 ⫻ 10⫺5 0.061 023 744 0.270 512 2 2.199 69 ⫻ 10⫺4 2.641 72 ⫻ 10⫺4 0.001 16.230 73 0.035 195 1 0.033 814 02 0.001 759 75 0.001 816 17 0.002 113 376 0.101 325 2.814 58 ⫻ 10⫺5 0.016 018 5 0.002 118 88 3.6 1 2.295 68 ⫻ 10⫺5 12 (1/128) (1/16) 1728 0.028 316 846 592 (1/27)

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TABLE 2.7 Conversion Factors (Continued) To convert Cubic foot (continued)

Cubic foot per hour Cubic foot per pound Cubic foot-atmosphere

Cubic inch Cubic inch per minute Cubic kilometer Cubic meter per kilogram Cubic yard

Cubic yard per minute

Cubit Cup (U.S.) Cup (metric) Curie Cycle per second Dalton Day (mean solar)

Debye Decibel Degree (plane angle)

Degree (angle) per foot Degree (angle) per second Degree Celsius

Degree Fahrenheit Degree Rankine Denier Dipole length (e cm)

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Into gallon (British) gallon (U.S.) liter liter per minute cubic meter per kilogram Btu calorie joule kilogram-meter liter-atmosphere watt-hour cubic foot milliliter* cubic centimeter per second cubic mile cubic foot per pound bushel (British) bushel (U.S.) cubic foot* cubic meter liter cubic foot per second* gallon (British) per second gallon (U.S.) per second liter per second inch* milliliter; centimeter3 cubic centimeter* becquerel* hertz* kilogram unified atomic mass* hour* minute* second* coulomb-meter neper circumference gon (grade) minute (angle)* quadrant radian revolution second (angle)* radian per meter radian per second degree Fahrenheit* degree Rankine* kelvin* degree Celsius kelvin tex coulomb-meter

Multiply by 6.228 835 7.480 519 28.316 847 0.471 947 0.062 428 0 2.719 48 685.298 2869.205 292.577 28.3168 0.797 001 (1/1728) 16.387 064 0.273 118 0.239 913 16.0185 21.0223 21.6962 27 0.764 554 86 764.555 0.45 2.802 98 3.366 23 12.742 58 18 236.6 200 3.7 ⫻ 1010 1 1.660 54 ⫻ 10⫺27 1 24 1440 86 400 3.335 64 ⫻ 10⫺30 0.115 129 255 (1/366) 1.111 11 60 (1/90) (␲/180) (1/360) 3600 0.057 261 5 0.017 453 3 1.8 1.8 1 (5/9) (5/9) (1/9) 1.602 18 ⫻ 10⫺21

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TABLE 2.7 Conversion Factors (Continued) To convert Drachm (British) Drachm (British, fluid)

Dram (apothecaries or troy)

Dram (weight)

Dram (U.S., fluid)

Dyne

Dyne per centimeter Dyne per square centimeter

Dyne-centimeter

Dyne-second/centimeter2 Electron charge Electron charge-centimeter (e cm) Electron charge-centimeter2 Electron mass Electronvolt

Ell Em, pica

Into

Multiply by

dram (apothecaries or troy)* cubic centimeter dram (U.S., fluid) minim (British) ounce (British, fluid) dram (weight) grain* gram* ounce (troy)* pennyweight* pound (troy)* scruple* grain* gram ounce (weight) pound (weight) cubic centimeter gallon (U.S.) gill (U.S.) milliliter minim (U.S.)* ounce (U.S., fluid) pint (U.S., fluid) kilogram (force) newton* pound (force) newton per meter* bar* kilogram per square centimeter millimeter of mercury (0⬚C) millimeter of water (4⬚C) newton per square meter* pascal* pound per square inch (psi) erg* foot-pound (force) foot-poundal joule* kilogram-meter (force) newton-meter* poise* pascal-second* coulomb coulomb-meter

1 3.551 633 0.960 760 60 (1/8) 2.194 285 7 60 3.887 934 6 (1/8) 2.5 (1/96) 3 27.343 75 1.771 845 2 (1/16) (1/256) 3.696 691 2 (1/1024) (1/32) 3.696 691 2 60 (1/8) (1/128) 1.019 716 ⫻ 10⫺6 10⫺5 2.248 09 ⫻ 10⫺6 0.001 10⫺6 1.019 716 ⫻ 10⫺6 7.500 617 ⫻ 10⫺4 0.010 197 16 0.1 0.1 1.450 38 ⫻ 10⫺5 1 7.375 62 ⫻ 10⫺8 2.373 04 ⫻ 10⫺6 10⫺7 1.019 716 ⫻ 10⫺8 10⫺7 1 0.1 1.602 18 ⫻ 10⫺19 1.602 18 ⫻ 10⫺21

coulomb-meter squared atomic mass unit gram erg joule kilojoule per mole inch* inch millimeter

1.602 18 ⫻ 10⫺23 0.000 548 6 9.1096 ⫻ 10⫺28 1.602 18 ⫻ 10⫺12 1.602 18 ⫻ 10⫺19 96.4853 45 0.167 4.217 52

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GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

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TABLE 2.7 Conversion Factors (Continued) To convert EMU1 of capacitance EMU of current EMU of electric potential EMU of inductance EMU of quantity (charge) EMU of resistance EMU of work ESU2 of capacitance ESU of current ESU of electric potential ESU of inductance ESU of quantity (charge) ESU of resistance ESU of work Erg

Erg per second Erg per (cm2 ⫻ second) Erg per gauss Fahrenheit scale Fahrenheit temperature (⬚F) Faraday (based on carbon-12) Faraday (chemical) Faraday (physical) Fathom Fermi Foot

Foot of water (4⬚C)

Foot per minute

Foot-candle

Foot-lambert

1 2

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Into farad* ampere* volt* henry* coulomb ohm joule farad ampere volt henry coulomb ohm joule dyne-centimeter* joule* watt-hour Btu watt* watt per square meter* ampere-centimeter squared* joule per tesla* centigrade scale Celsius temperature (⬚C) coulomb coulomb coulomb foot* meter meter* centimeter* inch* mile (nautical) mile (statute) yard atmosphere bar gram per square centimeter inch of mercury (0⬚C) pascal centimeter per second* knot mile per hour lumen per square foot* lumen per square meter lux candela per square centimeter candela per square foot lambert meter-lambert

EMU, the electromagnetic system of electrical units based on dynamics. ESU, the electrostatic system of electrical units based on static data.

Multiply by 109 10 10⫺8 10⫺9 10 10⫺9 10⫺7 1.112 650 ⫻ 10⫺12 3.335 641⫻ 10⫺10 299.792 5 8.987 552 ⫻ 1011 3.335 556 ⫻ 10⫺11 8.987 552 ⫻ 1011 10⫺7 1 10⫺7 2.777 78 ⫻ 10⫺11 5.69 ⫻ 10⫺6 10⫺7 0.001 10 0.001 (5/9) (⬚F ⫺ 32)(5/9) 96 487.0 96 495.7 96 521.9 6 1.828 8 10⫺15 30.48 12 1.645 788 ⫻ 10⫺4 1.893 939 ⫻ 10⫺4 (1/3) 0.029 499 8 0.029 499 8 30.48 0.882 671 2989.067 0.508 0.009 874 73 0.011 363 6 1 10.7639 10.76391 3.426 26 ⫻ 10⫺4 (1/␲) 0.001 076 39 10.7639

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TABLE 2.7 Conversion Factors (Continued) To convert Foot-pound

Foot-pound per minute

Foot-poundal

Franklin Franklin per cm3 Franklin per cm2 Furlong

Gallon (British, imperial)

Gallon (U.S.)

Gallon (U.S.) per minute

Gamma Gas constant

Gauss Gilbert

Into Btu calorie foot-poundal horsepower (British) joule kilogram-meter liter-atmosphere newton-meter watt-hour horsepower (British) horsepower (metric) watt Btu calorie foot-pound joule kilogram-meter liter-atmosphere watt-hour coulomb coulomb per cubic meter coulomb per square meter chain (Gunter’s)* foot* meter* mile bushel (British) cubic decimeter, liter* cubic foot gallon (U.S., fluid) gill (British)* liter ounce (British)* quart (British)* barrel (petroleum) cubic decimeter, liter cubic foot gallon (British) liter ounce (U.S., fluid)* quart (U.S., fluid)* cubic foot per hour cubic meter per hour liter per minute microgram* calorie per mole-degree joule per mole-degree liter-atmosphere per mole-degree tesla* weber per square meter* ampere-turn

Multiply by 0.001 285 07 0.323 832 32.1740 5.050 51 ⫻ 10⫺7 1.355 818 0.138 255 0.013 380 9 1.355 818 3.766 161 ⫻ 10⫺4 3.030 30 ⫻ 10⫺5 3.072 33 ⫻ 10⫺5 0.022 597 0 3.994 11 ⫻ 10⫺5 0.010 064 99 0.031 081 0 0.042 140 11 0.004 297 10 4.158 91 ⫻ 10⫺4 1.170 56 ⫻ 10⫺5 3.335 64 ⫻ 10⫺10 3.335 64 ⫻ 10⫺4 3.335 64 ⫻ 10⫺6 10 600 201.168 (1/8) (1/8) 4.546 90 0.160 544 1.200 95 32 4.546 09 160 4 (1/42) 3.785 41 0.133 680 56 0.832 674 3.785 41 128 4 8.020 83 0.227 125 3.785 412 1 1.987 8.3143 0.082 057 10⫺4 10⫺4 0.795 775

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TABLE 2.7 Conversion Factors (Continued) To convert Gill (British)

Gill (U.S.)

Gon (grade)

Grade Grain

Gram

Gram per (centimeter-second) Gram per cubic centimeter

Gram per square meter Gram per ton (long) Gram (force) Gram per square centimeter Gram-centimeter Gram-square centimeter Gray Hartree

Hectare

Hefner unit Hemisphere

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Into cubic centimeter, mL cubic inch gallon (British) gill (U.S.) ounce (British, fluid)* pint (British) cubic centimeter, mL gallon (U.S.) liter ounce (U.S., fluid)* quart (U.S.) circumference minute (angle)* radian radian carat (metric)* milligram* ounce (weight) ounce (troy) pennyweight pound scruple carat (metric)* dram grain ounce (weight) ounce (troy) pennyweight pound ton (metric)* poise* kilogram per liter* pound per cubic foot pound per gallon (U.S.) ounce per square foot gram per ton (metric) gram per ton (short) dyne* newton* pascal* joule* pound-square foot joule per kilogram* electron volt hertz joule acre are* meter squared candela sphere* spherical right angle* steradian

Multiply by 142.065 8.669 36 (1/32) 1.200 95 5 (1/4) 118.2941 (1/32) 0.118 294 1 4 (1/8) (1/400) 54 (2␲/400) (2␲/400) 0.323 994 55 64.798 91 0.002 285 714 3 (1/480) (1/24) (1/7000) (1/20) 5 0.564 383 39 15.432 358 0.035 273 962 0.032 150 747 0.643 014 93 0.002 204 622 6 10⫺6 1 1 62.4280 8.345 40 0.327 706 0.984 207 0.892 857 980.665 0.009 806 65 98.0665 9.806 65 ⫻ 10⫺5 2.373 04 ⫻ 10⫺6 1 27.211 40 6.579 683 90 ⫻ 1015 4.359 75 ⫻ 10⫺18 2.471 054 100 104 0.9 0.5 4 (2␲)

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TABLE 2.7 Conversion Factors (Continued) To convert Hertz Hogshead Horsepower (British)

Horsepower (electric) Horsepower-hour (British)

Hour (mean solar)

Hundredweight (long)

Hundredweight (short) Inch

Inch of mercury (0⬚C)

Inch of water (4⬚C)

Inch per minute

Joule

Into cycle per second* gallon (U.S.)* Btu per hour foot pound per hour* horsepower (metric) joule per second kilocalorie per hour kilogram-meter per second watt watt* Btu foot-pound* joule kilocalorie kilogram-meter watt-hour day minute* second* week kilogram* pound* ton (long) ton (metric) ton (short)* hundredweight (long) centimeter* foot mil* atmosphere inch of water (4⬚C) millibar millimeter of water (4⬚C) pascal pound per square inch, psi inch of mercury (0⬚C) millibar millimeter of mercury (0⬚C) pascal pound per square inch, psi foot per hour* meter per hour* millimeter per second Btu calorie* centigrade heat unit, chu centimeter-dyne* cubic foot-atmosphere cubic foot-(pound per in2) erg* foot-pound foot-poundal horsepower-hour (British) liter-atmosphere

Multiply by 1 63 2544.43 1.98 ⫻ 106 1.013 87 745.700 641.186 76.0402 745.70 746 2544.43 1.98 ⫻ 106 2.684 52 ⫻ 106 641.186 2.737 45 ⫻ 105 745.7 (1/24) 60 3600 (1/168) 50.802 345 44 112 (1/20) 0.050 802 345 0.056 0.892 857 2.54 (1/12) 1000 0.033 421 05 13.5951 33.863 88 345.316 3386.388 0.491 1541 0.073 5559 2.490 89 1.868 32 249.089 0.036 1273 5 1.524 0.423 333 9.478 170 ⫻ 10⫺4 0.2390 5.265 65 107 0.000 348 529 0.005 121 959 107 0.737 562 23.7304 3.725 06 ⫻ 10⫺7 0.009 869 233

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TABLE 2.7 Conversion Factors (Continued) To convert Joule (continued) Joule per centimeter

Joule per gram

Joule per second Kilogram (force)

Kilometer

Kilowatt

Kilowatt-hour

Knot

Lambda Lambert

Langley League (nautical) League (statute) Light-year Link Liter

Liter per minute

Liter-atmosphere

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Into newton-meter* watt-second* kilogram (force) newton* pound (force) Btu per pound kilocalorie per kilogram watt-hour per pound watt* dyne* newton* pound (force) poundal astronomical unit mile (nautical) mile (statute) Btu per minute foot-pound per second horsepower (British) horsepower (metric) joule per second* kilocalorie per hour Btu horsepower-hour (British) joule* kilocalorie foot per minute kilometer per hour* mile (nautical) per hour* mile (statute) per hour decimeter cubed* microliter* candela per square meter candela per square inch foot-lambert joule per square meter* mile (nautical)* mile (statute)* astronomical unit meter chain* cubic decimeter (dm3)* cubic foot gallon (British) gallon (U.S.) quart (British) quart (U.S.) cubic foot per hour gallon (British) per hour gallon (U.S.) per hour Btu calorie cubic foot-atmosphere cubic foot-pound per in2

Multiply by 1 1 10.197 16 100 22.4809 0.429 923 0.238 846 0.125 998 1 9.806 65 ⫻ 105 9.806 65 2.204 62 70.9316 6.684 59 ⫻ 10⫺9 0.539 956 80 0.621 371 192 56.8690 737.562 1.341 02 1.359 62 1000 859.845 3412.14 1.341 02 3.6 ⫻ 106 859.845 101.2686 1.852 1 1.150 78 10⫺6 1 (1/␲) ⫻ 104; 3183.099 2.053 61 929.030 4.184 ⫻ 104 3 3 6.323 97 ⫻ 104 9.460 73 ⫻ 1015 0.01 1 0.035 314 67 0.219 969 0.264 172 1 0.879 877 1.056 688 2.118 88 13.198 15.8503 0.096 037 6 24.2011 0.035 314 7 0.518 983

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TABLE 2.7 Conversion Factors (Continued) To convert Liter-atmosphere (continued)

Lumen per square centimeter Lumen per square meter Lux Maxwell Meter

Meter per second

Meter-candle Meter-lambert

Mho (ohm⫺1) Micron Mil Mile (nautical)

Mile (statute)

Mile per gallon (British) Mile per gallon (U.S.) Mile per hour

Milliliter Millimeter of mercury (0⬚C)

Into horsepower (British) horsepower (metric) joule* kilogram-meter watt-hour lux* phot* lumen per square foot lumen per square meter* weber* a˚ngstro¨m* fathom foot inch mile (nautical) mile (statute) foot per minute kilometer per hour* knot mile per hour lux* candela per square meter foot-lambert lambert* siemen* meter inch* micrometer* foot kilometer* mile (statute) chain (Gunter’s)* chain (Ramsden’s)* foot* furlong* kilometer* light-year link (Gunter’s)* link (Ramsden’s)* mile (nautical) rod* kilometer per liter kilometer per liter foot per minute kilometer per hour* knot cubic centimeter* atmosphere dyne per square centimeter millimeter of water (4⬚C) pascal pound per square inch (psi) torr*

Multiply by 3.774 42 ⫻ 10⫺5 3.826 77 ⫻ 10⫺5 101.325 10.332 27 0.028 145 8 104 1 0.092 903 0 1 10⫺8 1010 0.546 807 3.280 839 895 39.370 078 740 5.399 568 ⫻ 10⫺4 6.213 712 ⫻ 10⫺4 196.850 3.6 1.943 844 2.236 936 1 (1/␲) 0.092 903 0 10⫺4 1 10⫺6 0.001 25.4 6076.115 49 1.852 1.150 78 80 52.8 5280 8 1.609 344 1.701 11 ⫻ 10⫺11 8000 5280 0.868 976 320 0.354 006 0.425 144 88 1.609 344 0.868 976 1 (1/760) 1333.224 13.5951 133.322 0.019 336 8 1

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TABLE 2.7 Conversion Factors (Continued) To convert Millimeter of water (4⬚C)

Minim (British) Minim (U.S.) Minute (plane angle)

Minute Month (mean of 4-year period)

Nail (British) Nanometer Neper Nuclear magneton Neutron mass Newton

Newton per square meter Newton-meter

Nit Noggin (British) Nox Oersted Ohm (mean international) Ohm (U.S. international) Ohm per foot Ounce (avoirdupois)

Ounce (troy)

Ounce (British, fluid)

top of rh base of rh

Into atmosphere millibar* millimeter of mercury (0⬚C) pascal* pound per square inch milliliter minim (U.S.) milliliter circumference degree (angle) gon radian hour second day hour week inch* a˚ngstro¨m* decibel joule per tesla atomic mass unit gram dyne* kilogram (force) pound (force) poundal See pascal foot-pound joule* kilogram-meter watt-second* candela per square meter* gill (British)* lux* ampere per meter (in practice) ohm ohm ohm per meter dram* grain* gram* ounce (troy) pound grain* gram* ounce (avoirdupois) pennyweight* pound (avoirdupois) scruple* cubic centimeter gallon (British) milliliter

Multiply by 0.009 678 41 0.098 066 5 0.073 555 9 9.806 65 0.001 422 33 0.059 193 9 0.960 760 0.061 611 5 4.629 63 ⫻ 10⫺5 (1/60) (1/54) (␲/10,800) (1/60) 60 30.4375 730.5 4.348 21 2.25 10 8.685 890 5.050 79 ⫻ 10⫺27 1.008 66 1.6749 ⫻ 10⫺24 105 0.101 971 6 0.224 809 7.233 01 0.737 562 1 0.101 971 6 1 1 1 0.001 (1000/4␲); 79.577 47 1.000 49 1.000 495 3.280 84 16 437.5 28.349 5 0.911 458 33 (1/16) 480 31.1035 1.097 142 9 20 0.068 571 429 24 28.413 06 (1/160) 28.413 06

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TABLE 2.7 Conversion Factors (Continued) To convert Ounce (British, fluid) (continued)

Ounce (U.S., fluid)

Ounce (avoirdupois) per cubic foot Ounce (avoirdupois)/gallon (U.S.) Ounce (avoirdupois) per ton (long) Ounce (avoirdupois) per ton (short) Parsec Part per million Pascal

Pascal-second Peck (British) Peck (U.S.) Pennyweight

Phot Pica (printer’s) Pint (British)

Pint (U.S., dry)

Pint (U.S., fluid)

Into

Multiply by

minim (British) ounce (U.S., fluid) pint (British) quart (British) cubic centimeter gallon (U.S.) milliliter pint (U.S., fluid) quart (U.S., fluid) kilogram per cubic meter

480 0.960 760 (1/20) (1/40) 29.573 530 (1/128) 29.573 530 (1/16) (1/32) 1.001 154

gram per liter

7.489 15

gram per ton (metric)

27.9018

milligram per kilogram gram per ton (metric)*

27.9018 31.25

milligram per kilogram* light-year milligram per kilogram* milliliter per cubic meter* atmosphere bar* dyne per square centimeter* inch of mercury millimeter of mercury millimeter of water newton per square meter* pound per square inch poundal per square foot poise* gallon (British)* bushel (U.S.)* grain* gram* ounce (troy) pound lux* inch point* gallon (British) liter pint (U.S., fluid) quart (British) bushel (U.S.) liter peck (U.S.) pint (British) quart (U.S., dry) gallon (U.S.) liter

31.25 3.261 636 1 1 9.869 233 ⫻ 10⫺6 10⫺5 10 2.953 00 ⫻ 10⫺4 7.500 62 ⫻ 10⫺3 0.101 972 1 1.450 377 ⫻ 10⫺4 0.671 969 10 2 0.25 24 1.555 173 84 (1/20) 0.003 428 571 4 104 0.167 12 (1/8) 0.568 261 1.200 95 0.5 (1/64) 0.550 610 5 (1/16) 0.968 939 0.5 (1/8) 0.473 176 5

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TABLE 2.7 Conversion Factors (Continued) To convert Pint (U.S., fluid) (continued) Planck’s constant Point (printer’s, Didot) Point (printer’s, U.S.) Poise Polarizability volume (4␲⑀0 cm3) Pole (British) Pottle (British) Pound

Pound (troy)

Pound per cubic foot Pound per cubic inch Pound Pound Pound Pound Pound Pound Pound Pound

per foot per (foot-second) per gallon (U.S.) per hour per inch per minute per square foot (force)

Pound per square inch

Pound-second per square inch Poundal

Poundal per square foot Poundal-foot Poundal-second per square foot Proof (U.S.) Proton mass Puncheon (British)

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Into pint (British) quart (U.S., fluid)* joule-second millimeter millimeter* dyne-second per square centimeter* pascal-second* coulomb squared-(meter squared per joule) foot* gallon (British)* gram* ounce (weight)* ton (long) ton (short) grain gram* ounce (troy)* pennyweight pound (weight) scruple* kilogram per cubic meter gram per cubic centimeter pound per cubic foot* kilogram per meter pascal-second gram per liter kilogram per day kilogram per meter kilogram per hour kilogram per square meter kilogram (force) newton poundal atmosphere bar inch of mercury (0⬚C) millimeter of mercury (0⬚C) millimeter of water (4⬚C) pascal pound per square foot pascal-second gram (force) newton pound (force) pascal newton-meter pascal-second percent alcohol by volume* atomic mass unit gram gallon (British)

Multiply by 0.832 674 0.5 6.626 08 ⫻ 10⫺34 0.376 065 03 0.351 459 8 1 0.1 1.112 65 ⫻ 10⫺16 16.5 0.5 453.592 37 16 4.464 285 7 ⫻ 10⫺4 (1/2000) 5760 373.241 721 6 12 240 0.822 857 14 288 16.018 46 27.679 905 1728 1.488 16 1.488 16 119.8264 10.886 22 17.857 97 27.215 54 4.882 43 0.453 592 4.448 222 32.1740 0.068 046 0 0.068 948 0 2.036 02 51.7149 703.070 6894.757 144 6894.76 14.0981 0.138 255 0.031 081 0 1.488 164 0.042 140 1 1.488 164 0.5 1.007 28 1.6726 ⫻ 10⫺24 70

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TABLE 2.7 Conversion Factors (Continued) To convert Quad Quadrant

Quadrupole area (e cm2) Quart (British)

Quart (U.S., dry)

Quart (U.S., fluid)

Quartern (British, fluid) Quintal (metric) Rad (absorbed dose) Radian

Radian per centimeter Radian per second Radian per second squared Rankin (degree) Ream Register ton Rem (dose equivalent) Revolution

Revolution per minute Revolution per minute squared Revolution per second squared Reyn

Into Btu joule circumference* degree (angle)* gon (grade)* minute (angle)* radian coulomb meter squared gallon (British)* liter ounce (British, fluid)* pint (British)* quart (U.S., fluid) bushel (U.S.) cubic foot liter peck (U.S.) pint (U.S., dry)* gallon (U.S.)* liter ounce (U.S., fluid)* pint (U.S., fluid) quart (British) gill (British)* kilogram* gray* joule per kilogram* circumference degree (angle) minute (angle) quadrant revolution degree per millimeter degree per inch revolution per minute revolution per minute squared kelvin quire* sheet cubic foot* cubic meter sievert* degree (angle) gon* quadrant* radian degree (angle) per second* radian per second radian per second squared radian per second squared revolution per minute squared pascal-second pound-second per square inch

Multiply by 1015 1.055 ⫻ 1018 0.25 90 100 5400 (␲/2) 1.602 18 ⫻ 10⫺23 0.25 1.136 523 40 2 1.200 95 (1/32) 0.038 889 25 1.101 221 (1/8) 2 0.25 0.946 529 32 2 0.832 674 0.5 100 0.01 0.01 (1/2␲) 57.295 780 3437.75 (2/␲) (1/2␲) 5.729 58 145.531 9.549 30 572.958 (5/9) 20 480 or 500 100 2.831 685 0.01 360 400 4 (2␲) 6 0.104 720 0.001 745 33 6.283 185 3600 6894.76 1

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TABLE 2.7 Conversion Factors (Continued) To convert Rhe Right angle Rod (British, volume) Rod (surveyer’s measure)

Roentgen Rood (British) Rydberg Scruple

Second (plane angle)

Section Siemens Slug

Speed of light Sphere Square centimeter

Square chain (Gunter’s)

Square chain (Ramsden’s) Square degree (angle) Square foot

Square inch

Square kilometer

Square link (Gunter’s) Square link (Ramsden’s) Square meter

top of rh base of rh

Into per pascal-second* degree* radian cubic foot* chain (Gunter’s)* foot* link (Gunter’s)* meter* coulomb per kilogram acre* square meter joule dram (troy) grain* gram* ounce (weight) ounce (troy) pennyweight pound degree minute radian square mile* mho (ohm⫺1)* geepound* kilogram pound centimeter per second steradian circular mil circular millimeter square inch acre* square foot* square meter square foot* steradian acre square centimeter square meter square rod circular mil circular millimeter square centimeter acre hectare* square mile square foot* square foot* are* square foot square mile

Multiply by 10 90 (␲/2) 1000 0.25 16.5 25 5.0292 2.58 ⫻ 10⫺4 0.25 1011.714 1 2.179 87 ⫻ 10⫺18 (1/3) 20 1.295 978 2 0.045 714 286 (1/24) (10/12) (1/350) 2.777 78 ⫻ 10⫺4 (1/60) (␲/6.48 ⫻ 105) 1 1 1 14.593 90 32.1740 2.997 924 58 ⫻ 1010 (4␲) 1.973 53 ⫻ 105 127.3240 0.155 000 31 0.1 4356 404.686 104 3.046 17 ⫻ 10⫺4 2.295 68 ⫻ 10⫺5 929.0304 0.092 903 04 0.003 673 09 1.273 240 ⫻ 106 821.4432 6.4516 247.1054 100 0.386 102 16 0.4356 1 0.01 10.763 91 3.861 01 ⫻ 10⫺7

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TABLE 2.7 Conversion Factors (Continued) To convert Square meter (continued) Square mile

Square rod

Square yard

Statampere Statcoulomb Statfarad Stathenry Statmho Statohm Statvolt Statweber Steradian

Stere Stilb Stokes (kinematic viscosity) Stone (British) Svedberg Tablespoon (metric) Teaspoon (metric) Tesla Tex Therm Ton (assay) Ton (long)

Ton (metric)

Ton (short) Ton (force, long) Ton (force, metric)

Into square rod square yard acre* square kilometer township acre square foot square meter square foot* square inch* square meter* square rod ampere coulomb farad henry siemens ohm volt weber sphere spherical right angle square degree cubic meter* candela/cm2 square meter per second* pound* second* cubic centimeter*; milliter cubic centimeter*; milliliter weber per square meter* denier* gram per kilometer* Btu* joule* gram hundredweight (long)* hundredweight (short)* kilogram pound* ton (metric) ton (short) hundredweight (long) hundredweight (short) kilogram* pound ton (long) ton (short)* kilogram pound* newton newton

Multiply by 0.039 536 9 1.195 990 640 2.589 988 110 (1/36) (1/160) 272.25 25.292 853 9 1296 0.836 127 36 0.033 057 85 3.335 641 ⫻ 10⫺10 3.335 641 ⫻ 10⫺10 1.112 650 ⫻ 10⫺12 8.987 552 ⫻ 1011 1.112 650 ⫻ 10⫺12 8.987 552 ⫻ 1011 299.7925 299.7925 (1/4␲) (2/␲) 3282.81 1 1 10⫺4 14 10⫺13 14.79 4.929 1 9 1 105 1.054 804 ⫻ 108 29.166 67 20 22.4 1016.046 908 8 2240 1.016 046 9 1.12 19.684 131 22.046 226 1000 2204.6226 0.984 206 53 1.102 311 3 907.184 74 2000 1186.553 9806.65

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TABLE 2.7 Conversion Factors (Continued) To convert Ton (force, short) Ton (force, long)/ft2 Ton (force, metric)/m2 Ton (force, short)/ft2 Tonne (metric) Torr

Township (U.S.) Unified atomic mass unit Unit pole Volt (mean international) Volt (U.S. international) Volt-second Watt

Watt per square inch Watt-hour

Watt-second Weber Week Wey (British, capacity) Wey (British, mass) X unit Yard Year (mean of 4-years) Year (sidereal)

top of rh base of rh

Into newton bar pascal bar pascal bar pascal kilogram* atmosphere millibar millimeter of mercury* (0⬚C) pascal square kilometer square mile* kilogram weber volt volt weber* Btu per hour calorie per minute erg per second* foot-pound per minute horsepower (British) horsepower (metric) joule per second* kilogram-meter per second watt per square meter Btu calorie foot-pound horsepower-hour (British) horsepower-hour (metric) joule* liter-atmosphere joule* maxwell* day* hour* bushel (British) pound meter fathom* meter day week day (mean solar)

Multiply by 8896.44 1.072 518 1.072 518 ⫻ 105 0.098 066 5 9806.65 0.957 605 9.576 05 ⫻ 104 1000 (1/760) 1.333 224 1 133.322; (101 325/760) 93.2396 36 1.660 54 ⫻ 10⫺27 1.256 637 ⫻ 10⫺7 1.000 34 1.000 330 1 3.412 14 14.3308 107 44.2537 0.001 341 02 0.001 359 62 1 0.101 972 1550.003 3.412 14 859.845 2655.22 0.001 341 02 0.001 359 62 3600 35.5292 1 108 7 168 40 (variable) 252 (variable) 1.002 02 ⫻ 10⫺13 0.5 0.9144 365.25 52.178 87 365.256 36

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TABLE 2.8 Temperature Conversion Table The column of figures in bold and which is headed “Reading in ⬚F. or ⬚C. to be converted” refers to the temperature either in degrees Fahrenheit or Celsius which it is desired to convert into the other scale. If converting from Fahrenheit degrees to Celsius degrees, the equivalent temperature will be found in the column headed “⬚C.”; while if converting from degrees Celsius to degrees Fahrenheit, the equivalent temperature will be found in the column headed “⬚F.” This arrangement is very similar to that of Sauveur and Boylston, copyrighted 1920, and is published with their permission.

⬚F.

Reading in ⬚F. or ⬚C. to be converted

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⬚C.

........ ........ ........ ........ ........

⫺458 ⫺456 ⫺454 ⫺452 ⫺450

⫺272.22 ⫺271.11 ⫺270.00 ⫺268.89 ⫺267.78

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

⫺378 ⫺376 ⫺374 ⫺372 ⫺370

⫺227.78 ⫺226.67 ⫺225.56 ⫺224.44 ⫺223.33

........ ........ ........ ........ ........

⫺448 ⫺446 ⫺444 ⫺442 ⫺440

⫺266.67 ⫺265.56 ⫺264.44 ⫺263.33 ⫺262.22

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

⫺368 ⫺366 ⫺364 ⫺362 ⫺360

⫺222.22 ⫺221.11 ⫺220.00 ⫺218.89 ⫺217.78

........ ........ ........ ........ ........

⫺438 ⫺436 ⫺434 ⫺432 ⫺430

⫺261.11 ⫺260.00 ⫺258.89 ⫺257.78 ⫺256.67

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

⫺358 ⫺356 ⫺354 ⫺352 ⫺350

⫺216.67 ⫺215.56 ⫺214.44 ⫺213.33 ⫺212.22

........ ........ ........ ........ ........

⫺428 ⫺426 ⫺424 ⫺422 ⫺420

⫺255.56 ⫺254.44 ⫺253.33 ⫺252.22 ⫺251.11

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

⫺348 ⫺346 ⫺344 ⫺342 ⫺340

⫺211.11 ⫺210.00 ⫺208.89 ⫺207.78 ⫺206.67

........ ........ ........ ........ ........

⫺418 ⫺416 ⫺414 ⫺412 ⫺410

⫺250.00 ⫺248.89 ⫺247.78 ⫺246.67 ⫺245.56

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

⫺338 ⫺336 ⫺334 ⫺332 ⫺330

⫺205.56 ⫺204.44 ⫺203.33 ⫺202.22 ⫺201.11

........ ........ ........ ........ ........

⫺408 ⫺406 ⫺404 ⫺402 ⫺400

⫺244.44 ⫺243.33 ⫺242.22 ⫺241.11 ⫺240.00

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

⫺328 ⫺326 ⫺324 ⫺322 ⫺320

⫺200.00 ⫺198.89 ⫺197.78 ⫺196.67 ⫺195.56

........ ........ ........ ........ ........

⫺398 ⫺396 ⫺394 ⫺392 ⫺390

⫺238.89 ⫺237.78 ⫺236.67 ⫺235.56 ⫺234.44

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

⫺318 ⫺316 ⫺314 ⫺312 ⫺310

⫺194.44 ⫺193.33 ⫺192.22 ⫺191.11 ⫺190.00

........ ........ ........ ........ ........

⫺388 ⫺386 ⫺384 ⫺382 ⫺380

⫺233.33 ⫺232.22 ⫺231.11 ⫺230.00 ⫺228.89

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

⫺308 ⫺306 ⫺304 ⫺302 ⫺300

⫺188.89 ⫺187.78 ⫺186.67 ⫺185.56 ⫺184.44

⬚F.

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TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

top of rh base of rh

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

. . . . .

. . . . .

. . . . .

..... ..... ..... ..... .....

⫺298 ⫺296 ⫺294 ⫺292 ⫺290

⫺183.33 ⫺182.22 ⫺181.11 ⫺180.00 ⫺178.89

⫺342.4 ⫺338.8 ⫺335.2 ⫺331.6 ⫺328.0

⫺208 ⫺206 ⫺204 ⫺202 ⫺200

⫺133.33 ⫺132.22 ⫺131.11 ⫺130.00 ⫺128.89

. . . . .

. . . . .

. . . . .

..... ..... ..... ..... .....

⫺288 ⫺286 ⫺284 ⫺282 ⫺280

⫺177.78 ⫺176.67 ⫺175.56 ⫺174.44 ⫺173.33

⫺324.4 ⫺320.8 ⫺317.2 ⫺313.6 ⫺310.0

⫺198 ⫺196 ⫺194 ⫺192 ⫺190

⫺127.78 ⫺126.67 ⫺125.56 ⫺124.44 ⫺123.33

........ ........ ........ ⫺457.6 ⫺454.0

⫺278 ⫺276 ⫺274 ⫺272 ⫺270

⫺172.22 ⫺171.11 ⫺170.00 ⫺168.89 ⫺167.78

⫺306.4 ⫺302.8 ⫺299.2 ⫺295.6 ⫺292.0

⫺188 ⫺186 ⫺184 ⫺182 ⫺180

⫺122.22 ⫺121.11 ⫺120.00 ⫺118.89 ⫺117.78

⫺450.4 ⫺446.8 ⫺443.2 ⫺439.6 ⫺436.0

⫺268 ⫺266 ⫺264 ⫺262 ⫺260

⫺166.67 ⫺165.56 ⫺164.44 ⫺163.33 ⫺162.22

⫺288.4 ⫺284.8 ⫺281.2 ⫺277.6 ⫺274.0

⫺178 ⫺176 ⫺174 ⫺172 ⫺170

⫺116.67 ⫺115.56 ⫺114.44 ⫺113.33 ⫺112.22

⫺432.4 ⫺428.8 ⫺425.2 ⫺421.6 ⫺418.0

⫺258 ⫺256 ⫺254 ⫺252 ⫺250

⫺161.11 ⫺160.00 ⫺158.89 ⫺157.78 ⫺156.67

⫺270.4 ⫺266.8 ⫺263.2 ⫺259.6 ⫺256.0

⫺168 ⫺166 ⫺164 ⫺162 ⫺160

⫺111.11 ⫺110.00 ⫺108.89 ⫺107.78 ⫺106.67

⫺414.4 ⫺410.8 ⫺407.2 ⫺403.6 ⫺400.0

⫺248 ⫺246 ⫺244 ⫺242 ⫺240

⫺155.56 ⫺154.44 ⫺153.33 ⫺152.22 ⫺151.11

⫺252.4 ⫺248.8 ⫺245.2 ⫺241.6 ⫺238.0

⫺158 ⫺156 ⫺154 ⫺152 ⫺150

⫺105.56 ⫺104.44 ⫺103.33 ⫺102.22 ⫺101.11

⫺396.4 ⫺392.8 ⫺389.2 ⫺385.6 ⫺382.0

⫺238 ⫺236 ⫺234 ⫺232 ⫺230

⫺150.00 ⫺148.89 ⫺147.78 ⫺146.67 ⫺145.56

⫺234.4 ⫺230.8 ⫺227.2 ⫺223.6 ⫺220.0

⫺148 ⫺146 ⫺144 ⫺142 ⫺140

⫺100.00 ⫺98.89 ⫺97.78 ⫺96.67 ⫺95.56

⫺378.4 ⫺374.8 ⫺371.2 ⫺367.6 ⫺364.0

⫺228 ⫺226 ⫺224 ⫺222 ⫺220

⫺144.44 ⫺143.33 ⫺142.22 ⫺141.11 ⫺140.00

⫺216.4 ⫺212.8 ⫺209.2 ⫺205.6 ⫺202.0

⫺138 ⫺136 ⫺134 ⫺132 ⫺130

⫺94.44 ⫺93.33 ⫺92.22 ⫺91.11 ⫺90.00

⫺360.4 ⫺356.8 ⫺353.2 ⫺349.6 ⫺346.0

⫺218 ⫺216 ⫺214 ⫺212 ⫺210

⫺138.89 ⫺137.78 ⫺136.67 ⫺135.56 ⫺134.44

⫺198.4 ⫺194.8 ⫺191.2 ⫺187.6 ⫺184.0

⫺128 ⫺126 ⫺124 ⫺122 ⫺120

⫺88.89 ⫺87.78 ⫺86.67 ⫺85.56 ⫺84.44

short standard long

DEAN #37261

LEFT

(McGHP)

2.56

INTERACTIVE

top of rh base of rh

SECTION 2

cap height base of text

TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⫺180.4 ⫺176.8 ⫺173.2 ⫺169.6 ⫺166.0

⫺118 ⫺116 ⫺114 ⫺112 ⫺110

⫺83.33 ⫺82.22 ⫺81.11 ⫺80.00 ⫺78.89

⫺18.4 ⫺14.8 ⫺11.2 ⫺7.6 ⫺4.0

⫺28 ⫺26 ⫺24 ⫺22 ⫺20

⫺33.33 ⫺32.22 ⫺31.11 ⫺30.00 ⫺28.89

⫺162.4 ⫺158.8 ⫺155.2 ⫺151.6 ⫺148.0

⫺108 ⫺106 ⫺104 ⫺102 ⫺100

⫺77.78 ⫺76.67 ⫺75.56 ⫺74.44 ⫺73.33

⫺0.4 ⫹3.2 ⫹6.8 ⫹10.4 ⫹14.0

⫺18 ⫺16 ⫺14 ⫺12 ⫺10

⫺27.78 ⫺26.67 ⫺25.56 ⫺24.44 ⫺23.33

⫺144.4 ⫺140.8 ⫺137.2 ⫺133.6 ⫺130.0

⫺98 ⫺96 ⫺94 ⫺92 ⫺90

⫺72.22 ⫺71.11 ⫺70.00 ⫺68.89 ⫺67.78

⫹17.6 ⫹19.4 ⫹21.2 ⫹23.0 ⫹24.8

⫺8 ⫺7 ⫺6 ⫺5 ⫺4

⫺22.22 ⫺21.67 ⫺21.11 ⫺20.56 ⫺20.00

⫺126.4 ⫺122.8 ⫺119.2 ⫺115.6 ⫺112.0

⫺88 ⫺86 ⫺84 ⫺82 ⫺80

⫺66.67 ⫺65.56 ⫺64.44 ⫺63.33 ⫺62.22

⫹26.6 ⫹28.4 ⫹30.2 ⫹32.0 ⫹33.8

⫺3 ⫺2 ⫺1 ⫾0 ⫹1

⫺19.44 ⫺18.89 ⫺18.33 ⫺17.78 ⫺17.22

⫺108.4 ⫺104.8 ⫺101.2 ⫺97.6 ⫺94.0

⫺78 ⫺76 ⫺74 ⫺72 ⫺70

⫺61.11 ⫺60.00 ⫺58.89 ⫺57.78 ⫺56.67

⫹35.6 ⫹37.4 ⫹39.2 ⫹41.0 ⫹42.8

⫹2 ⫹3 ⫹4 ⫹5 ⫹6

⫺16.67 ⫺16.11 ⫺15.56 ⫺15.00 ⫺14.44

⫺90.4 ⫺86.8 ⫺83.2 ⫺79.6 ⫺76.0

⫺68 ⫺66 ⫺64 ⫺62 ⫺60

⫺55.56 ⫺54.44 ⫺53.33 ⫺52.22 ⫺51.11

⫹44.6 ⫹46.4 ⫹48.2 ⫹50.0 ⫹51.8

⫹7 ⫹8 ⫹9 ⫹10 ⫹11

⫺13.89 ⫺13.33 ⫺12.78 ⫺12.22 ⫺11.67

⫺72.4 ⫺68.8 ⫺65.2 ⫺61.6 ⫺58.0

⫺58 ⫺56 ⫺54 ⫺52 ⫺50

⫺50.00 ⫺48.89 ⫺47.78 ⫺46.67 ⫺45.56

⫹53.6 ⫹55.4 ⫹57.2 ⫹59.0 ⫹60.8

⫹12 ⫹13 ⫹14 ⫹15 ⫹16

⫺11.11 ⫺10.56 ⫺10.00 ⫺9.44 ⫺8.89

⫺54.4 ⫺50.8 ⫺47.2 ⫺43.6 ⫺40.0

⫺48 ⫺46 ⫺44 ⫺42 ⫺40

⫺44.44 ⫺43.33 ⫺42.22 ⫺41.11 ⫺40.00

⫹62.6 ⫹64.4 ⫹66.2 ⫹68.0 ⫹69.8

⫹17 ⫹18 ⫹19 ⫹20 ⫹21

⫺8.33 ⫺7.78 ⫺7.22 ⫺6.67 ⫺6.11

⫺36.4 ⫺32.8 ⫺29.2 ⫺25.6 ⫺22.0

⫺38 ⫺36 ⫺34 ⫺32 ⫺30

⫺38.89 ⫺37.78 ⫺36.67 ⫺35.56 ⫺34.44

⫹71.6 ⫹73.4 ⫹75.2 ⫹77.0 ⫹78.8

⫹22 ⫹23 ⫹24 ⫹25 ⫹26

⫺5.56 ⫺5.00 ⫺4.44 ⫺3.89 ⫺3.33

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

2.57

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

cap height base of text

TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

top of rh base of rh

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⫹80.6 ⫹82.4 ⫹84.2 ⫹86.0 ⫹87.8

⫹27 ⫹28 ⫹29 ⫹30 ⫹31

⫺2.78 ⫺2.22 ⫺1.67 ⫺1.11 ⫺0.56

⫹161.6 ⫹163.4 ⫹165.2 ⫹167.0 ⫹168.8

⫹72 ⫹73 ⫹74 ⫹75 ⫹76

⫹22.22 ⫹22.78 ⫹23.33 ⫹23.89 ⫹24.44

⫹89.6 ⫹91.4 ⫹93.2 ⫹95.0 ⫹96.8

⫹32 ⫹33 ⫹34 ⫹35 ⫹36

⫾0.00 ⫹0.56 ⫹1.11 ⫹1.67 ⫹2.22

⫹170.6 ⫹172.4 ⫹174.2 ⫹176.0 ⫹177.8

⫹77 ⫹78 ⫹79 ⫹80 ⫹81

⫹25.00 ⫹25.56 ⫹26.11 ⫹26.67 ⫹27.22

⫹98.6 ⫹100.4 ⫹102.2 ⫹104.0 ⫹105.8

⫹37 ⫹38 ⫹39 ⫹40 ⫹41

⫹2.78 ⫹3.33 ⫹3.89 ⫹4.44 ⫹5.00

⫹179.6 ⫹181.4 ⫹183.2 ⫹185.0 ⫹186.8

⫹82 ⫹83 ⫹84 ⫹85 ⫹86

⫹27.78 ⫹28.33 ⫹28.89 ⫹29.44 ⫹30.00

⫹107.6 ⫹109.4 ⫹111.2 ⫹113.0 ⫹114.8

⫹42 ⫹43 ⫹44 ⫹45 ⫹46

⫹5.56 ⫹6.11 ⫹6.67 ⫹7.22 ⫹7.78

⫹188.6 ⫹190.4 ⫹192.2 ⫹194.0 ⫹195.8

⫹87 ⫹88 ⫹89 ⫹90 ⫹91

⫹30.56 ⫹31.11 ⫹31.67 ⫹32.22 ⫹32.78

⫹116.6 ⫹118.4 ⫹120.2 ⫹122.0 ⫹123.8

⫹47 ⫹48 ⫹49 ⫹50 ⫹51

⫹8.33 ⫹8.89 ⫹9.44 ⫹10.00 ⫹10.56

⫹197.6 ⫹199.4 ⫹201.2 ⫹203.0 ⫹204.8

⫹92 ⫹93 ⫹94 ⫹95 ⫹96

⫹33.33 ⫹33.89 ⫹34.44 ⫹35.00 ⫹35.56

⫹125.6 ⫹127.4 ⫹129.2 ⫹131.0 ⫹132.8

⫹52 ⫹53 ⫹54 ⫹55 ⫹56

⫹11.11 ⫹11.67 ⫹12.22 ⫹12.78 ⫹13.33

⫹206.6 ⫹208.4 ⫹210.2 ⫹212.0 ⫹213.8

⫹97 ⫹98 ⫹99 ⫹100 ⫹101

⫹36.11 ⫹36.67 ⫹37.22 ⫹37.78 ⫹38.33

⫹134.6 ⫹136.4 ⫹138.2 ⫹140.0 ⫹141.8

⫹57 ⫹58 ⫹59 ⫹60 ⫹61

⫹13.89 ⫹14.44 ⫹15.00 ⫹15.56 ⫹16.11

⫹215.6 ⫹217.4 ⫹219.2 ⫹221.0 ⫹222.8

⫹102 ⫹103 ⫹104 ⫹105 ⫹106

⫹38.89 ⫹39.44 ⫹40.00 ⫹40.56 ⫹41.11

⫹143.6 ⫹145.4 ⫹147.2 ⫹149.0 ⫹150.8

⫹62 ⫹63 ⫹64 ⫹65 ⫹66

⫹16.67 ⫹17.22 ⫹17.78 ⫹18.33 ⫹18.89

⫹224.6 ⫹226.4 ⫹228.2 ⫹230.0 ⫹231.8

⫹107 ⫹108 ⫹109 ⫹110 ⫹111

⫹41.67 ⫹42.22 ⫹42.78 ⫹43.33 ⫹43.89

⫹152.6 ⫹154.4 ⫹156.2 ⫹158.0 ⫹159.8

⫹67 ⫹68 ⫹69 ⫹70 ⫹71

⫹19.44 ⫹20.00 ⫹20.56 ⫹21.11 ⫹21.67

⫹233.6 ⫹235.4 ⫹237.2 ⫹239.0 ⫹240.8

⫹112 ⫹113 ⫹114 ⫹115 ⫹116

⫹44.44 ⫹45.00 ⫹45.56 ⫹46.11 ⫹46.67

short standard long

DEAN #37261

LEFT

(McGHP)

2.58

INTERACTIVE

top of rh base of rh

SECTION 2

cap height base of text

TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⬚C.

⫹242.6 ⫹244.4 ⫹246.2 ⫹248.0 ⫹249.8

⫹117 ⫹118 ⫹119 ⫹120 ⫹121

⫹47.22 ⫹47.78 ⫹48.33 ⫹48.89 ⫹49.44

⫹323.6 ⫹325.4 ⫹327.2 ⫹329.0 ⫹330.8

⫹162 ⫹163 ⫹164 ⫹165 ⫹166

⫹72.22 ⫹72.78 ⫹73.33 ⫹73.89 ⫹74.44

⫹251.6 ⫹253.4 ⫹255.2 ⫹257.0 ⫹258.8

⫹122 ⫹123 ⫹124 ⫹125 ⫹126

⫹50.00 ⫹50.56 ⫹51.11 ⫹51.67 ⫹52.22

⫹332.6 ⫹334.4 ⫹336.2 ⫹338.0 ⫹339.8

⫹167 ⫹168 ⫹169 ⫹170 ⫹171

⫹75.00 ⫹75.56 ⫹76.11 ⫹76.67 ⫹77.22

⫹260.6 ⫹262.4 ⫹264.2 ⫹266.0 ⫹267.8

⫹127 ⫹128 ⫹129 ⫹130 ⫹131

⫹52.78 ⫹53.33 ⫹53.89 ⫹54.44 ⫹55.00

⫹341.6 ⫹343.4 ⫹345.2 ⫹347.0 ⫹348.8

⫹172 ⫹173 ⫹174 ⫹175 ⫹176

⫹77.78 ⫹78.33 ⫹78.89 ⫹79.44 ⫹80.00

⫹269.6 ⫹271.4 ⫹273.2 ⫹275.0 ⫹276.8

⫹132 ⫹133 ⫹134 ⫹135 ⫹136

⫹55.56 ⫹56.11 ⫹56.67 ⫹57.22 ⫹57.78

⫹350.6 ⫹352.4 ⫹354.2 ⫹356.0 ⫹357.8

⫹177 ⫹178 ⫹179 ⫹180 ⫹181

⫹80.56 ⫹81.11 ⫹81.67 ⫹82.22 ⫹82.78

⫹278.6 ⫹280.4 ⫹282.2 ⫹284.0 ⫹285.8

⫹137 ⫹138 ⫹139 ⫹140 ⫹141

⫹58.33 ⫹58.89 ⫹59.44 ⫹60.00 ⫹60.56

⫹359.6 ⫹361.4 ⫹363.2 ⫹365.0 ⫹366.8

⫹182 ⫹183 ⫹184 ⫹185 ⫹186

⫹83.33 ⫹83.89 ⫹84.44 ⫹85.00 ⫹85.56

⫹287.6 ⫹289.4 ⫹291.2 ⫹293.0 ⫹294.8

⫹142 ⫹143 ⫹144 ⫹145 ⫹146

⫹61.11 ⫹61.67 ⫹62.22 ⫹62.78 ⫹63.33

⫹368.6 ⫹370.4 ⫹372.2 ⫹374.0 ⫹375.8

⫹187 ⫹188 ⫹189 ⫹190 ⫹191

⫹86.11 ⫹86.67 ⫹87.22 ⫹87.78 ⫹88.33

⫹296.6 ⫹298.4 ⫹300.2 ⫹302.0 ⫹303.8

⫹147 ⫹148 ⫹149 ⫹150 ⫹151

⫹63.89 ⫹64.44 ⫹65.00 ⫹65.56 ⫹66.11

⫹377.6 ⫹379.4 ⫹381.2 ⫹383.0 ⫹384.8

⫹192 ⫹193 ⫹194 ⫹195 ⫹196

⫹88.89 ⫹89.44 ⫹90.00 ⫹90.56 ⫹91.11

⫹305.6 ⫹307.4 ⫹309.2 ⫹311.0 ⫹312.8

⫹152 ⫹153 ⫹154 ⫹155 ⫹156

⫹66.67 ⫹67.22 ⫹67.78 ⫹68.33 ⫹68.89

⫹386.6 ⫹388.4 ⫹390.2 ⫹392.0 ⫹393.8

⫹197 ⫹198 ⫹199 ⫹200 ⫹201

⫹91.67 ⫹92.22 ⫹92.78 ⫹93.33 ⫹93.89

⫹314.6 ⫹316.4 ⫹318.2 ⫹320.0 ⫹321.8

⫹157 ⫹158 ⫹159 ⫹160 ⫹161

⫹69.44 ⫹70.00 ⫹70.56 ⫹71.11 ⫹71.67

⫹395.6 ⫹397.4 ⫹399.2 ⫹401.0 ⫹402.8

⫹202 ⫹203 ⫹204 ⫹205 ⫹206

⫹94.44 ⫹95.00 ⫹95.56 ⫹96.11 ⫹96.67

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

2.59

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

cap height base of text

TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⫹404.6 ⫹406.4 ⫹408.2 ⫹410.0 ⫹411.8

⫹207 ⫹208 ⫹209 ⫹210 ⫹211

⫹413.6 ⫹415.4 ⫹417.2 ⫹419.0 ⫹420.8

top of rh base of rh

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⫹97.22 ⫹97.78 ⫹98.33 ⫹98.89 ⫹99.44

⫹543.2 ⫹546.8 ⫹550.4 ⫹554.0 ⫹557.6

⫹284 ⫹286 ⫹288 ⫹290 ⫹292

⫹140.00 ⫹141.11 ⫹142.22 ⫹143.33 ⫹144.44

⫹212 ⫹213 ⫹214 ⫹215 ⫹216

⫹100.00 ⫹100.56 ⫹101.11 ⫹101.67 ⫹102.22

⫹561.2 ⫹564.8 ⫹568.4 ⫹572.0 ⫹575.6

⫹294 ⫹296 ⫹298 ⫹300 ⫹302

⫹145.56 ⫹146.67 ⫹147.78 ⫹148.89 ⫹150.00

⫹422.6 ⫹424.4 ⫹426.2 ⫹428.0 ⫹431.6

⫹217 ⫹218 ⫹219 ⫹220 ⫹222

⫹102.78 ⫹103.33 ⫹103.89 ⫹104.44 ⫹105.56

⫹579.2 ⫹582.8 ⫹586.4 ⫹590.0 ⫹593.6

⫹304 ⫹306 ⫹308 ⫹310 ⫹312

⫹151.11 ⫹152.22 ⫹153.33 ⫹154.44 ⫹155.56

⫹435.2 ⫹438.8 ⫹442.4 ⫹446.0 ⫹449.6

⫹224 ⫹226 ⫹228 ⫹230 ⫹232

⫹106.67 ⫹107.78 ⫹108.89 ⫹110.00 ⫹111.11

⫹597.2 ⫹600.8 ⫹604.4 ⫹608.0 ⫹611.6

⫹314 ⫹316 ⫹318 ⫹320 ⫹322

⫹156.67 ⫹157.78 ⫹158.89 ⫹160.00 ⫹161.11

⫹453.2 ⫹456.8 ⫹460.4 ⫹464.0 ⫹467.6

⫹234 ⫹236 ⫹238 ⫹240 ⫹242

⫹112.22 ⫹113.33 ⫹114.44 ⫹115.56 ⫹116.67

⫹615.2 ⫹618.8 ⫹622.4 ⫹626.0 ⫹629.6

⫹324 ⫹326 ⫹328 ⫹330 ⫹332

⫹162.22 ⫹163.33 ⫹164.44 ⫹165.56 ⫹166.67

⫹471.2 ⫹474.8 ⫹478.4 ⫹482.0 ⫹485.6

⫹244 ⫹246 ⫹248 ⫹250 ⫹252

⫹117.78 ⫹118.89 ⫹120.00 ⫹121.11 ⫹122.22

⫹633.2 ⫹636.8 ⫹640.4 ⫹644.0 ⫹647.6

⫹334 ⫹336 ⫹338 ⫹340 ⫹342

⫹167.78 ⫹168.89 ⫹170.00 ⫹171.11 ⫹172.22

⫹489.2 ⫹492.8 ⫹496.4 ⫹500.0 ⫹503.6

⫹254 ⫹256 ⫹258 ⫹260 ⫹262

⫹123.33 ⫹124.44 ⫹125.56 ⫹126.67 ⫹127.78

⫹651.2 ⫹654.8 ⫹658.4 ⫹662.0 ⫹665.6

⫹344 ⫹346 ⫹348 ⫹350 ⫹352

⫹173.33 ⫹174.44 ⫹175.56 ⫹176.67 ⫹177.78

⫹507.2 ⫹510.8 ⫹514.4 ⫹518.0 ⫹521.6

⫹264 ⫹266 ⫹268 ⫹270 ⫹272

⫹128.89 ⫹130.00 ⫹131.11 ⫹132.22 ⫹133.33

⫹669.2 ⫹672.8 ⫹676.4 ⫹680.0 ⫹683.6

⫹354 ⫹356 ⫹358 ⫹360 ⫹362

⫹178.89 ⫹180.00 ⫹181.11 ⫹182.22 ⫹183.33

⫹525.2 ⫹528.8 ⫹532.4 ⫹536.0 ⫹539.6

⫹274 ⫹276 ⫹278 ⫹280 ⫹282

⫹134.44 ⫹135.56 ⫹136.67 ⫹137.78 ⫹138.89

⫹687.2 ⫹690.8 ⫹694.4 ⫹698.0 ⫹701.6

⫹364 ⫹366 ⫹368 ⫹370 ⫹372

⫹184.44 ⫹185.56 ⫹186.67 ⫹187.78 ⫹188.89

short standard long

DEAN #37261

LEFT

(McGHP)

2.60

INTERACTIVE

top of rh base of rh

SECTION 2

cap height base of text

TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⬚C.

⫹705.2 ⫹708.8 ⫹712.4 ⫹716.0 ⫹719.6

⫹374 ⫹376 ⫹378 ⫹380 ⫹382

⫹190.00 ⫹191.11 ⫹192.22 ⫹193.33 ⫹194.44

⫹867.2 ⫹870.8 ⫹874.4 ⫹878.0 ⫹881.6

⫹464 ⫹466 ⫹468 ⫹470 ⫹472

⫹240.00 ⫹241.11 ⫹242.22 ⫹243.33 ⫹244.44

⫹723.2 ⫹726.8 ⫹730.4 ⫹734.0 ⫹737.6

⫹384 ⫹386 ⫹388 ⫹390 ⫹392

⫹195.56 ⫹196.67 ⫹197.78 ⫹198.89 ⫹200.00

⫹885.2 ⫹888.8 ⫹892.4 ⫹896.0 ⫹899.6

⫹474 ⫹476 ⫹478 ⫹480 ⫹482

⫹245.56 ⫹246.67 ⫹247.78 ⫹248.89 ⫹250.00

⫹741.2 ⫹744.8 ⫹748.4 ⫹752.0 ⫹755.6

⫹394 ⫹396 ⫹398 ⫹400 ⫹402

⫹201.11 ⫹202.22 ⫹203.33 ⫹204.44 ⫹205.56

⫹903.2 ⫹906.8 ⫹910.4 ⫹914.0 ⫹917.6

⫹484 ⫹486 ⫹488 ⫹490 ⫹492

⫹251.11 ⫹252.22 ⫹253.33 ⫹254.44 ⫹255.56

⫹759.2 ⫹762.8 ⫹766.4 ⫹770.0 ⫹773.6

⫹404 ⫹406 ⫹408 ⫹410 ⫹412

⫹206.67 ⫹207.78 ⫹208.89 ⫹210.00 ⫹211.11

⫹921.2 ⫹924.8 ⫹928.4 ⫹932.0 ⫹935.6

⫹494 ⫹496 ⫹498 ⫹500 ⫹502

⫹256.67 ⫹257.78 ⫹258.89 ⫹260.00 ⫹261.11

⫹777.2 ⫹780.8 ⫹784.4 ⫹788.0 ⫹791.6

⫹414 ⫹416 ⫹418 ⫹420 ⫹422

⫹212.22 ⫹213.33 ⫹214.44 ⫹215.56 ⫹216.67

⫹939.2 ⫹942.8 ⫹946.4 ⫹950.0 ⫹953.6

⫹504 ⫹506 ⫹508 ⫹510 ⫹512

⫹262.22 ⫹263.33 ⫹264.44 ⫹265.56 ⫹266.67

⫹795.2 ⫹798.8 ⫹802.4 ⫹806.0 ⫹809.6

⫹424 ⫹426 ⫹428 ⫹430 ⫹432

⫹217.78 ⫹218.89 ⫹220.00 ⫹221.11 ⫹222.22

⫹957.2 ⫹960.8 ⫹964.4 ⫹968.0 ⫹971.6

⫹514 ⫹516 ⫹518 ⫹520 ⫹522

⫹267.78 ⫹268.89 ⫹270.00 ⫹271.11 ⫹272.22

⫹813.2 ⫹816.8 ⫹820.4 ⫹824.0 ⫹827.6

⫹434 ⫹436 ⫹438 ⫹440 ⫹442

⫹223.33 ⫹224.44 ⫹225.56 ⫹226.67 ⫹227.78

⫹975.2 ⫹978.8 ⫹982.4 ⫹986.0 ⫹989.6

⫹524 ⫹526 ⫹528 ⫹530 ⫹532

⫹273.33 ⫹274.44 ⫹275.56 ⫹276.67 ⫹277.78

⫹831.2 ⫹834.8 ⫹838.4 ⫹842.0 ⫹845.6

⫹444 ⫹446 ⫹448 ⫹450 ⫹452

⫹228.89 ⫹230.00 ⫹231.11 ⫹232.22 ⫹233.33

⫹993.2 ⫹996.8 ⫹1000.4 ⫹1004.0 ⫹1007.6

⫹534 ⫹536 ⫹538 ⫹540 ⫹542

⫹278.89 ⫹280.00 ⫹281.11 ⫹282.22 ⫹283.33

⫹849.2 ⫹852.8 ⫹856.4 ⫹860.0 ⫹863.6

⫹454 ⫹456 ⫹458 ⫹460 ⫹462

⫹234.44 ⫹235.56 ⫹236.67 ⫹237.78 ⫹238.89

⫹1011.2 ⫹1014.8 ⫹1018.4 ⫹1022.0 ⫹1025.6

⫹544 ⫹546 ⫹548 ⫹550 ⫹552

⫹284.44 ⫹285.56 ⫹286.67 ⫹287.78 ⫹288.89

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

2.61

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

cap height base of text

TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⫹1029.2 ⫹1032.8 ⫹1036.4 ⫹1040.0 ⫹1043.6

⫹554 ⫹556 ⫹558 ⫹560 ⫹562

⫹1047.2 ⫹1050.8 ⫹1054.4 ⫹1058.0 ⫹1061.6

top of rh base of rh

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⫹290.00 ⫹291.11 ⫹292.22 ⫹293.33 ⫹294.44

⫹1191.2 ⫹1194.8 ⫹1198.4 ⫹1202.0 ⫹1205.6

⫹644 ⫹646 ⫹648 ⫹650 ⫹652

⫹340.00 ⫹341.11 ⫹342.22 ⫹343.33 ⫹344.44

⫹564 ⫹566 ⫹568 ⫹570 ⫹572

⫹295.56 ⫹296.67 ⫹297.78 ⫹298.89 ⫹300.00

⫹1209.2 ⫹1212.8 ⫹1216.4 ⫹1220.0 ⫹1223.6

⫹654 ⫹656 ⫹658 ⫹660 ⫹662

⫹345.56 ⫹346.67 ⫹347.78 ⫹348.89 ⫹350.00

⫹1065.2 ⫹1068.8 ⫹1072.4 ⫹1076.0 ⫹1079.6

⫹574 ⫹576 ⫹578 ⫹580 ⫹582

⫹301.11 ⫹302.22 ⫹303.33 ⫹304.44 ⫹305.56

⫹1227.2 ⫹1230.8 ⫹1234.4 ⫹1238.0 ⫹1241.6

⫹664 ⫹666 ⫹668 ⫹670 ⫹672

⫹351.11 ⫹352.22 ⫹353.33 ⫹354.44 ⫹355.56

⫹1083.2 ⫹1086.8 ⫹1090.4 ⫹1094.0 ⫹1097.6

⫹584 ⫹586 ⫹588 ⫹590 ⫹592

⫹306.67 ⫹307.78 ⫹308.89 ⫹310.00 ⫹311.11

⫹1245.2 ⫹1248.8 ⫹1252.4 ⫹1256.0 ⫹1259.6

⫹674 ⫹676 ⫹678 ⫹680 ⫹682

⫹356.67 ⫹357.78 ⫹358.89 ⫹360.00 ⫹361.11

⫹1101.2 ⫹1104.8 ⫹1108.4 ⫹1112.0 ⫹1115.6

⫹594 ⫹596 ⫹598 ⫹600 ⫹602

⫹312.22 ⫹313.33 ⫹314.44 ⫹315.56 ⫹316.67

⫹1263.2 ⫹1266.8 ⫹1270.4 ⫹1274.0 ⫹1277.6

⫹684 ⫹686 ⫹688 ⫹690 ⫹692

⫹362.22 ⫹363.33 ⫹364.44 ⫹365.56 ⫹366.67

⫹1119.2 ⫹1122.8 ⫹1126.4 ⫹1130.0 ⫹1133.6

⫹604 ⫹606 ⫹608 ⫹610 ⫹612

⫹317.78 ⫹318.89 ⫹320.00 ⫹321.11 ⫹322.22

⫹1281.2 ⫹1284.8 ⫹1288.4 ⫹1292.0 ⫹1295.6

⫹694 ⫹696 ⫹698 ⫹700 ⫹702

⫹367.78 ⫹368.89 ⫹370.00 ⫹371.11 ⫹372.22

⫹1137.2 ⫹1140.8 ⫹1144.4 ⫹1148.0 ⫹1151.6

⫹614 ⫹616 ⫹618 ⫹620 ⫹622

⫹323.33 ⫹324.44 ⫹325.56 ⫹326.67 ⫹327.78

⫹1299.2 ⫹1302.8 ⫹1306.4 ⫹1310.0 ⫹1313.6

⫹704 ⫹706 ⫹708 ⫹710 ⫹712

⫹373.33 ⫹374.44 ⫹375.56 ⫹376.67 ⫹377.78

⫹1155.2 ⫹1158.8 ⫹1162.4 ⫹1166.0 ⫹1169.6

⫹624 ⫹626 ⫹628 ⫹630 ⫹632

⫹328.89 ⫹330.00 ⫹331.11 ⫹332.22 ⫹333.33

⫹1317.2 ⫹1320.8 ⫹1324.4 ⫹1328.0 ⫹1331.6

⫹714 ⫹716 ⫹718 ⫹720 ⫹722

⫹378.89 ⫹380.00 ⫹381.11 ⫹382.22 ⫹383.33

⫹1173.2 ⫹1176.8 ⫹1180.4 ⫹1184.0 ⫹1187.6

⫹634 ⫹636 ⫹638 ⫹640 ⫹642

⫹334.44 ⫹335.56 ⫹336.67 ⫹337.78 ⫹338.89

⫹1335.2 ⫹1338.8 ⫹1342.4 ⫹1346.0 ⫹1349.6

⫹724 ⫹726 ⫹728 ⫹730 ⫹732

⫹384.44 ⫹385.56 ⫹386.67 ⫹387.78 ⫹388.89

short standard long

DEAN #37261

LEFT

(McGHP)

2.62

INTERACTIVE

top of rh base of rh

SECTION 2

cap height base of text

TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⬚C.

⫹1353.2 ⫹1356.8 ⫹1360.4 ⫹1364.0 ⫹1367.6

⫹734 ⫹736 ⫹738 ⫹740 ⫹742

⫹390.00 ⫹391.11 ⫹392.22 ⫹393.33 ⫹394.44

⫹1515.2 ⫹1518.8 ⫹1522.4 ⫹1526.0 ⫹1529.6

⫹824 ⫹826 ⫹828 ⫹830 ⫹832

⫹440.00 ⫹441.11 ⫹442.22 ⫹443.33 ⫹444.44

⫹1371.2 ⫹1374.8 ⫹1378.4 ⫹1382.0 ⫹1385.6

⫹744 ⫹746 ⫹748 ⫹750 ⫹752

⫹395.56 ⫹396.67 ⫹397.78 ⫹398.89 ⫹400.00

⫹1533.2 ⫹1536.8 ⫹1540.4 ⫹1544.0 ⫹1547.6

⫹834 ⫹836 ⫹838 ⫹840 ⫹842

⫹445.56 ⫹446.67 ⫹447.78 ⫹448.89 ⫹450.00

⫹1389.2 ⫹1392.8 ⫹1396.4 ⫹1400.0 ⫹1403.6

⫹754 ⫹756 ⫹758 ⫹760 ⫹762

⫹401.11 ⫹402.22 ⫹403.33 ⫹404.44 ⫹405.56

⫹1551.2 ⫹1554.8 ⫹1558.4 ⫹1562.0 ⫹1565.6

⫹844 ⫹846 ⫹848 ⫹850 ⫹852

⫹451.11 ⫹452.22 ⫹453.33 ⫹454.44 ⫹455.56

⫹1407.2 ⫹1410.8 ⫹1414.4 ⫹1418.0 ⫹1421.6

⫹764 ⫹766 ⫹768 ⫹770 ⫹772

⫹406.67 ⫹407.78 ⫹408.89 ⫹410.00 ⫹411.11

⫹1569.2 ⫹1572.8 ⫹1576.4 ⫹1580.0 ⫹1583.6

⫹854 ⫹856 ⫹858 ⫹860 ⫹862

⫹456.67 ⫹457.78 ⫹458.89 ⫹460.00 ⫹461.11

⫹1425.2 ⫹1428.8 ⫹1432.4 ⫹1436.0 ⫹1439.6

⫹774 ⫹776 ⫹778 ⫹780 ⫹782

⫹412.22 ⫹413.33 ⫹414.44 ⫹415.56 ⫹416.67

⫹1587.2 ⫹1590.8 ⫹1594.4 ⫹1598.0 ⫹1601.6

⫹864 ⫹866 ⫹868 ⫹870 ⫹872

⫹462.22 ⫹463.33 ⫹464.44 ⫹465.56 ⫹466.67

⫹1443.2 ⫹1446.8 ⫹1450.4 ⫹1454.0 ⫹1457.6

⫹784 ⫹786 ⫹788 ⫹790 ⫹792

⫹417.78 ⫹418.89 ⫹420.00 ⫹421.11 ⫹422.22

⫹1605.2 ⫹1608.8 ⫹1612.4 ⫹1616.0 ⫹1619.6

⫹874 ⫹876 ⫹878 ⫹880 ⫹882

⫹467.78 ⫹468.89 ⫹470.00 ⫹471.11 ⫹472.22

⫹1461.2 ⫹1464.8 ⫹1468.4 ⫹1472.0 ⫹1475.6

⫹794 ⫹796 ⫹798 ⫹800 ⫹802

⫹423.33 ⫹424.44 ⫹425.56 ⫹426.67 ⫹427.78

⫹1623.2 ⫹1626.8 ⫹1630.4 ⫹1634.0 ⫹1637.6

⫹884 ⫹886 ⫹888 ⫹890 ⫹892

⫹473.33 ⫹474.44 ⫹475.56 ⫹476.67 ⫹477.78

⫹1479.2 ⫹1482.8 ⫹1486.4 ⫹1490.0 ⫹1493.6

⫹804 ⫹806 ⫹808 ⫹810 ⫹812

⫹428.89 ⫹430.00 ⫹431.11 ⫹432.22 ⫹433.33

⫹1641.2 ⫹1644.8 ⫹1648.4 ⫹1652.0 ⫹1655.6

⫹894 ⫹896 ⫹898 ⫹900 ⫹902

⫹478.89 ⫹480.00 ⫹481.11 ⫹482.22 ⫹483.33

⫹1497.2 ⫹1500.8 ⫹1504.4 ⫹1508.0 ⫹1511.6

⫹814 ⫹816 ⫹818 ⫹820 ⫹822

⫹434.44 ⫹435.56 ⫹436.67 ⫹437.78 ⫹438.89

⫹1659.2 ⫹1662.8 ⫹1666.4 ⫹1670.0 ⫹1673.6

⫹904 ⫹906 ⫹908 ⫹910 ⫹912

⫹484.44 ⫹485.56 ⫹486.67 ⫹487.78 ⫹488.89

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

2.63

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

cap height base of text

TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⫹1677.2 ⫹1680.8 ⫹1684.4 ⫹1688.0 ⫹1691.6

⫹914 ⫹916 ⫹918 ⫹920 ⫹922

⫹1695.2 ⫹1698.8 ⫹1702.4 ⫹1706.0 ⫹1709.6

top of rh base of rh

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⫹490.00 ⫹491.11 ⫹492.22 ⫹493.33 ⫹494.44

⫹1868.0 ⫹1886.0 ⫹1904.0 ⫹1922.0 ⫹1940.0

⫹1020 ⫹1030 ⫹1040 ⫹1050 ⫹1060

⫹548.89 ⫹554.44 ⫹560.00 ⫹565.56 ⫹571.11

⫹924 ⫹926 ⫹928 ⫹930 ⫹932

⫹495.56 ⫹496.67 ⫹497.78 ⫹498.89 ⫹500.00

⫹1958.0 ⫹1976.0 ⫹1994.0 ⫹2012.0 ⫹2030.0

⫹1070 ⫹1080 ⫹1090 ⫹1100 ⫹1110

⫹576.67 ⫹582.22 ⫹587.78 ⫹593.33 ⫹598.89

⫹1713.2 ⫹1716.8 ⫹1720.4 ⫹1724.0 ⫹1727.6

⫹934 ⫹936 ⫹938 ⫹940 ⫹942

⫹501.11 ⫹502.22 ⫹503.33 ⫹504.44 ⫹505.56

⫹2048.0 ⫹2066.0 ⫹2084.0 ⫹2102.0 ⫹2120.0

⫹1120 ⫹1130 ⫹1140 ⫹1150 ⫹1160

⫹604.44 ⫹610.00 ⫹615.56 ⫹621.11 ⫹626.67

⫹1731.2 ⫹1734.8 ⫹1738.4 ⫹1742.0 ⫹1745.6

⫹944 ⫹946 ⫹948 ⫹950 ⫹952

⫹506.67 ⫹507.78 ⫹508.89 ⫹510.00 ⫹511.11

⫹2138.0 ⫹2156.0 ⫹2174.0 ⫹2192.0 ⫹2210.0

⫹1170 ⫹1180 ⫹1190 ⫹1200 ⫹1210

⫹632.22 ⫹637.78 ⫹643.33 ⫹648.89 ⫹654.44

⫹1749.2 ⫹1752.8 ⫹1756.4 ⫹1760.0 ⫹1763.6

⫹954 ⫹956 ⫹958 ⫹960 ⫹962

⫹512.22 ⫹513.33 ⫹514.44 ⫹515.56 ⫹516.67

⫹2228.0 ⫹2246.0 ⫹2264.0 ⫹2282.0 ⫹2300.0

⫹1220 ⫹1230 ⫹1240 ⫹1250 ⫹1260

⫹660.00 ⫹665.56 ⫹671.11 ⫹676.67 ⫹682.22

⫹1767.2 ⫹1770.8 ⫹1774.4 ⫹1778.0 ⫹1781.6

⫹964 ⫹966 ⫹968 ⫹970 ⫹972

⫹517.78 ⫹518.89 ⫹520.00 ⫹521.11 ⫹522.22

⫹2318.0 ⫹2336.0 ⫹2354.0 ⫹2372.0 ⫹2390.0

⫹1270 ⫹1280 ⫹1290 ⫹1300 ⫹1310

⫹687.78 ⫹693.33 ⫹698.89 ⫹704.44 ⫹710.00

⫹1785.2 ⫹1788.8 ⫹1792.4 ⫹1796.0 ⫹1799.6

⫹974 ⫹976 ⫹978 ⫹980 ⫹982

⫹523.33 ⫹524.44 ⫹525.56 ⫹526.67 ⫹527.78

⫹2408.0 ⫹2426.0 ⫹2444.0 ⫹2462.0 ⫹2480.0

⫹1320 ⫹1330 ⫹1340 ⫹1350 ⫹1360

⫹715.56 ⫹721.11 ⫹726.67 ⫹732.22 ⫹737.78

⫹1803.2 ⫹1806.8 ⫹1810.4 ⫹1814.0 ⫹1817.6

⫹984 ⫹986 ⫹988 ⫹990 ⫹992

⫹528.89 ⫹530.00 ⫹531.11 ⫹532.22 ⫹533.33

⫹2498.0 ⫹2516.0 ⫹2534.0 ⫹2552.0 ⫹2570.0

⫹1370 ⫹1380 ⫹1390 ⫹1400 ⫹1410

⫹743.33 ⫹748.89 ⫹754.44 ⫹760.00 ⫹765.56

⫹1821.2 ⫹1824.8 ⫹1828.4 ⫹1832.0 ⫹1850.0

⫹994 ⫹996 ⫹998 ⫹1000 ⫹1010

⫹534.44 ⫹535.56 ⫹536.67 ⫹537.78 ⫹543.33

⫹2588.0 ⫹2606.0 ⫹2624.0 ⫹2642.0 ⫹2660.0

⫹1420 ⫹1430 ⫹1440 ⫹1450 ⫹1460

⫹771.11 ⫹776.67 ⫹782.22 ⫹787.78 ⫹793.33

short standard long

DEAN #37261

LEFT

(McGHP)

2.64

INTERACTIVE

top of rh base of rh

SECTION 2

cap height base of text

TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⬚C.

⫹2678.0 ⫹2696.0 ⫹2714.0 ⫹2732.0 ⫹2750.0

⫹1470 ⫹1480 ⫹1490 ⫹1500 ⫹1510

⫹798.89 ⫹804.44 ⫹810.00 ⫹815.56 ⫹821.11

⫹3488.0 ⫹3506.0 ⫹3524.0 ⫹3542.0 ⫹3560.0

⫹1920 ⫹1930 ⫹1940 ⫹1950 ⫹1960

⫹1048.9 ⫹1054.4 ⫹1060.0 ⫹1065.6 ⫹1071.1

⫹2768.0 ⫹2786.0 ⫹2804.0 ⫹2822.0 ⫹2840.0

⫹1520 ⫹1530 ⫹1540 ⫹1550 ⫹1560

⫹826.67 ⫹832.22 ⫹837.78 ⫹843.33 ⫹848.89

⫹3578.0 ⫹3596.0 ⫹3614.0 ⫹3632.0 ⫹3650.0

⫹1970 ⫹1980 ⫹1990 ⫹2000 ⫹2010

⫹1076.7 ⫹1082.2 ⫹1087.8 ⫹1093.3 ⫹1098.9

⫹2858.0 ⫹2876.0 ⫹2894.0 ⫹2912.0 ⫹2930.0

⫹1570 ⫹1580 ⫹1590 ⫹1600 ⫹1610

⫹854.44 ⫹860.00 ⫹865.56 ⫹871.11 ⫹876.67

⫹3668.0 ⫹3686.0 ⫹3704.0 ⫹3722.0 ⫹3740.0

⫹2020 ⫹2030 ⫹2040 ⫹2050 ⫹2060

⫹1104.4 ⫹1110.0 ⫹1115.6 ⫹1121.1 ⫹1126.7

⫹2948.0 ⫹2966.0 ⫹2984.0 ⫹3002.0 ⫹3020.0

⫹1620 ⫹1630 ⫹1640 ⫹1650 ⫹1660

⫹882.22 ⫹887.78 ⫹893.33 ⫹898.89 ⫹904.44

⫹3758.0 ⫹3776.0 ⫹3794.0 ⫹3812.0 ⫹3830.0

⫹2070 ⫹2080 ⫹2090 ⫹2100 ⫹2110

⫹1132.2 ⫹1137.8 ⫹1143.3 ⫹1148.9 ⫹1154.4

⫹3038.0 ⫹3056.0 ⫹3074.0 ⫹3092.0 ⫹3110.0

⫹1670 ⫹1680 ⫹1690 ⫹1700 ⫹1710

⫹910.00 ⫹915.56 ⫹921.11 ⫹926.67 ⫹932.22

⫹3848.0 ⫹3866.0 ⫹3884.0 ⫹3902.0 ⫹3920.0

⫹2120 ⫹2130 ⫹2140 ⫹2150 ⫹2160

⫹1160.0 ⫹1165.6 ⫹1171.1 ⫹1176.7 ⫹1182.2

⫹3128.0 ⫹3146.0 ⫹3164.0 ⫹3182.0 ⫹3200.0

⫹1720 ⫹1730 ⫹1740 ⫹1750 ⫹1760

⫹937.78 ⫹943.33 ⫹948.89 ⫹954.44 ⫹960.00

⫹3938.0 ⫹3956.0 ⫹3974.0 ⫹3992.0 ⫹4010.0

⫹2170 ⫹2180 ⫹2190 ⫹2200 ⫹2210

⫹1187.8 ⫹1193.3 ⫹1198.9 ⫹1204.4 ⫹1210.0

⫹3218.0 ⫹3236.0 ⫹3254.0 ⫹3272.0 ⫹3290.0

⫹1770 ⫹1780 ⫹1790 ⫹1800 ⫹1810

⫹965.56 ⫹971.11 ⫹976.67 ⫹982.22 ⫹987.78

⫹4028.0 ⫹4046.0 ⫹4064.0 ⫹4082.0 ⫹4100.0

⫹2220 ⫹2230 ⫹2240 ⫹2250 ⫹2260

⫹1215.6 ⫹1221.1 ⫹1226.7 ⫹1232.2 ⫹1237.8

⫹3308.0 ⫹3326.0 ⫹3344.0 ⫹3362.0 ⫹3380.0

⫹1820 ⫹1830 ⫹1840 ⫹1850 ⫹1860

⫹993.33 ⫹998.89 ⫹1004.4 ⫹1010.0 ⫹1015.6

⫹4118.0 ⫹4136.0 ⫹4154.0 ⫹4172.0 ⫹4190.0

⫹2270 ⫹2280 ⫹2290 ⫹2300 ⫹2310

⫹1243.3 ⫹1248.9 ⫹1254.4 ⫹1260.0 ⫹1265.6

⫹3398.0 ⫹3416.0 ⫹3434.0 ⫹3452.0 ⫹3470.0

⫹1870 ⫹1880 ⫹1890 ⫹1900 ⫹1910

⫹1021.1 ⫹1026.7 ⫹1032.2 ⫹1037.8 ⫹1043.3

⫹4208.0 ⫹4226.0 ⫹4244.0 ⫹4262.0 ⫹4280.0

⫹2320 ⫹2330 ⫹2340 ⫹2350 ⫹2360

⫹1271.1 ⫹1276.7 ⫹1282.2 ⫹1287.8 ⫹1293.3

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TABLE 2.8 Temperature Conversion Table (Continued)

⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⫹4298.0 ⫹4316.0 ⫹4334.0 ⫹4352.0 ⫹4370.0

⫹2370 ⫹2380 ⫹2390 ⫹2400 ⫹2410

⫹4388.0 ⫹4406.0 ⫹4424.0 ⫹4442.0 ⫹4460.0

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⬚F.

Reading in ⬚F. or ⬚C. to be converted

⬚C.

⫹1298.9 ⫹1304.4 ⫹1310.0 ⫹1315.6 ⫹1321.1

⫹4964.0 ⫹4982.0 ⫹5000.0 ⫹5018.0 ⫹5036.0

⫹2740 ⫹2750 ⫹2760 ⫹2770 ⫹2780

⫹1504.4 ⫹1510.0 ⫹1515.6 ⫹1521.1 ⫹1526.7

⫹2420 ⫹2430 ⫹2440 ⫹2450 ⫹2460

⫹1326.7 ⫹1332.2 ⫹1337.8 ⫹1343.3 ⫹1348.9

⫹5054.0 ⫹5072.0 ⫹5090.0 ⫹5108.0 ⫹5126.0

⫹2790 ⫹2800 ⫹2810 ⫹2820 ⫹2830

⫹1532.2 ⫹1537.8 ⫹1543.3 ⫹1548.9 ⫹1554.4

⫹4478.0 ⫹4496.0 ⫹4514.0 ⫹4532.0 ⫹4550.0 ⫹4568.0 ⫹4586.0

⫹2470 ⫹2480 ⫹2490 ⫹2500 ⫹2510 ⫹2520 ⫹2530

⫹1354.4 ⫹1360.0 ⫹1365.6 ⫹1371.1 ⫹1376.7 ⫹1382.2 ⫹1387.8

⫹5144.0 ⫹5162.0 ⫹5180.0 ⫹5198.0 ⫹5216.0

⫹2840 ⫹2850 ⫹2860 ⫹2870 ⫹2880

⫹1560.0 ⫹1565.6 ⫹1571.1 ⫹1576.7 ⫹1582.2

⫹4604.0 ⫹4622.0 ⫹4640.0 ⫹4658.0 ⫹4676.0

⫹2540 ⫹2550 ⫹2560 ⫹2570 ⫹2580

⫹1393.3 ⫹1398.9 ⫹1404.4 ⫹1410.0 ⫹1415.6

⫹5234.0 ⫹5252.0 ⫹5270.0 ⫹5288.0 ⫹5306.0

⫹2890 ⫹2900 ⫹2910 ⫹2920 ⫹2930

⫹1587.8 ⫹1593.3 ⫹1598.9 ⫹1604.4 ⫹1610.0

⫹4694.0 ⫹4712.0 ⫹4730.0 ⫹4748.0 ⫹4766.0

⫹2590 ⫹2600 ⫹2610 ⫹2620 ⫹2630

⫹1421.1 ⫹1426.7 ⫹1432.2 ⫹1437.8 ⫹1443.3

⫹5324.0 ⫹5342.0 ⫹5360.0 ⫹5378.0 ⫹5396.0

⫹2940 ⫹2950 ⫹2960 ⫹2970 ⫹2980

⫹1615.6 ⫹1621.1 ⫹1626.7 ⫹1632.2 ⫹1637.8

⫹4784.0 ⫹4802.0 ⫹4820.0 ⫹4838.0 ⫹4856.0

⫹2640 ⫹2650 ⫹2660 ⫹2670 ⫹2680

⫹1448.9 ⫹1454.4 ⫹1460.0 ⫹1465.6 ⫹1471.1

⫹5414.0 ⫹5432.0 ⫹5450.0 ⫹5468.0 ⫹5486.0

⫹2990 ⫹3000 ⫹3010 ⫹3020 ⫹3030

⫹1643.3 ⫹1648.9 ⫹1654.4 ⫹1660.0 ⫹1665.6

⫹4874.0 ⫹4892.0 ⫹4910.0 ⫹4928.0 ⫹4946.0

⫹2690 ⫹2700 ⫹2710 ⫹2720 ⫹2730

⫹1476.7 ⫹1482.2 ⫹1487.8 ⫹1493.3 ⫹1498.9

⫹5504.0 ⫹5522.0 ⫹5540.0 ⫹5558.0 ⫹5576.0 ⫹5594.0 ⫹5612.0

⫹3040 ⫹3050 ⫹3060 ⫹3070 ⫹3080 ⫹3090 ⫹3100

⫹1671.1 ⫹1676.7 ⫹1682.2 ⫹1687.8 ⫹1693.3 ⫹1698.9 ⫹1704.4

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Conversion of Thermometer Scales

The following abbreviations are used: ⬚F, degrees Fahrenheit; ⬚C, degrees Celsius; ⬚K, degrees Kelvin; ⬚Re´, degrees Reaumur; ⬚R, degrees Rankine; ⬚Z, degrees on any scale; (fp)“Z”, the freezing point of water on the Z scale; and (bp)“Z”, the boiling point of water on the Z scale. Reference: Dodds, Chemical and Metallurgical Engineering 38:476 (1931). ⬚F ⫺ 32 ⬚C ⬚Re´ K ⫺ 273 ⬚R ⫺ 492 ⬚Z ⫺ (fp)“Z” ⫽ ⫽ ⫽ ⫽ ⫽ 180 100 80 100 180 (bp)“Z” ⫺ (fp)“Z” Examples (1) To find the Fahrenheit temperature corresponding to ⫺20⬚C: ⬚F ⫺ 32 ⬚C ⫽ 180 100 ⬚F ⫺ 32 ⫽

⬚F ⫺ 32 ⫺20 ⫽ 180 100

or

(⫺20)(180) ⫽ ⫺36 100 ⬚F ⫽ ⫺4

(2) To find the Reaumur temperature corresponding to 20⬚F: ⬚F ⫺ 32 ⬚Re´ 20 ⫺ 32 ⬚Re´ ⫽ ⫽ ⫽ 180 80 180 80 i.e.,

20⬚F ⫽ ⫺5.33⬚Re´

(3) To find the correct temperature on a thermometer reading 80⬚C and that shows a reading of ⫺0.30⬚C in a melting ice/water mixture and 99.0⬚C in steam at 760 mm pressure of mercury: ⬚C Z ⫺ (fp)“Z” 80 ⫺ (⫺0.30) ⫽ ⫽ 100 (bp)“Z” ⫺ (fp)“Z” 99.0 ⫺ (⫺0.30) i.e.,

2.1.2 2.1.2.1

⬚C ⫽ 80.87

(corrected)

Density and Specific Gravity Hydrometers. Various hydrometers and the relation between the various scales.

Alcoholometer. This hydrometer is used in determining the density of aqueous ethyl alcohol solutions; the reading in degrees is numerically the same as the percentage of alcohol by volume. The scale known as Tralle gives the percentage by volume. Wine and Must hydrometer relations are given below. Ammoniameter. This hydrometer, employed in finding the density of aqueous ammonia solutions, has a scale graduated in equal divisions from 0⬚ to 40⬚. To convert the reading to specific gravity multiply by 3 and subtract the resulting number from 1000. Balling Hydrometer. See under Saccharometers. Barkometer or Barktrometer. This hydrometer, which is used in determining the density of tanning liquors, has a scale from 0⬚ to 80⬚ Bk; the number to the right of the decimal point of a specific gravity reading is the corresponding Bk degree; thus, a specific gravity of 1.015 is 15⬚ Bk.

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Baume´ Hydrometers. For liquids heavier than water: This hydrometer was originally based on the density of a 10% sodium chloride solution, which was given the value of 10⬚, and the density of pure water, which was given the value of 0⬚; the interval between these two values was divided into 10 equal parts. Other reference points have been taken with the result that so much confusion exists that there are about 36 different scales in use, many of which are incorrect. In general a Baume´ hydrometer should have inscribed on it the temperature at which it was calibrated and also the temperature of the water used in relating the density to a specific gravity. The following expression gives the relation between the specific gravity and several of the Baume´ scales:

Specific gravity ⫽ m ⫽ 145 at 60⬚/60⬚F (15.56⬚C) ⫽ 144

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m m ⫺ Baume´

for the American Scale

for the old scale used in Holland

⫽ 146.3 at 15⬚C

for the Gerlach Scale

⫽ 144.3 at 15⬚C

for the Rational Scale generally used in Germany

For liquids lighter than water: Originally the density of a solution of 1 gram of sodium chloride in 9 grams of water at 12.5⬚C was given a value of 10⬚Be´. The scale between these points was divided into ten equal parts and these divisions were repeated throughout the scale giving a relation which could be expressed by the formula: Specific gravity ⫽ 145.88/(135.88 ⫹ Be´), which is approximately equal to 146/(136 ⫹ Be´). Other scales have since come into more general use such as that of the Bureau of Standards in which the specific gravity at 60⬚/60⬚F ⫽ 140/(130 ⫹ Be´) and that of the American Petroleum Institute (A.P.I. Scale) in which the specific gravity at 60⬚/60⬚F ⫽ 141.5/(131.5 ⫹ API⬚). See also special table for conversion to density and Twaddell scale. Beck’s Hydrometer. This hydrometer is graduated to show a reading of 0⬚ in pure water and a reading of 30⬚ in a solution with a specific gravity of 0.850, with equal scale divisions above and below these two points. Brix Hydrometer. See under Saccharometers. Cartier’s Hydrometer. This hydrometer shows a reading of 22⬚ when immersed in a solution having a density of 22⬚ Baume´ but the scale divisions are smaller than on the Baume´ hydrometer in the ratio of 16 Cartier to 15 Baume´. Fatty Oil Hydrometer. The graduations on this hydrometer are in specific gravity within the range 0.908 to 0.938. The letters on the scale correspond to the specific gravity of the various common oils as follows: R, rape; O, olive; A, almond; S, sesame; HL, hoof oil; HP, hemp; C, cotton seed; L, linseed. See also Oleometer below. Lactometers. These hydrometers are used in determining the density of milk. The various scales in common use are the following: New York Board of Health has a scale graduated into 120 equal parts, 0⬚ being equal to the specific gravity of water and 100⬚ being equal to a specific gravity of 1.029. Quevenne lactometer is graduated from 15⬚ to 40⬚ corresponding to specific gravities from 1.015 to 1.040. Soxhlet lactometer has a scale from 25⬚ to 35⬚ corresponding to specific gravities from 1.025 to 1.035 respectively.

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Oleometer. A hydrometer for determining the density of vegetable and sperm oils with a scale from 50⬚ to 0⬚ corresponding to specific gravities from 0.870 to 0.970. See also Fatty Oil Hydrometer above.

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Saccharometers. These hydrometers are used in determining the density of sugar solutions. Solutions of the same concentration but of different carbohydrates have very nearly the same specific gravity and in general a concentration of 10 grams of carbohydrate per 100 mL of solution shows a specific gravity of 1.0386. Thus, the wt. of sugar in 1000 mL soln. is (a) for conc. ⬍12g/100 mL: (wt. of 1000 mL soln. ⫺ 1000) ⫼ 0.386; (b) for conc. ⬎12g/100 mL: (wt of 1000 mL soln. ⫺ 1000) ⫼ 0.385. Brix hydrometer is graduated so that the number of degrees is identical with the percentage by weight of cane sugar and is used at the temperature indicated on the hydrometer. Balling’s saccharometer is used in Europe and is practically identical with the Brix hydrometer. Bates brewers’ saccharometer which is used in determining the density of malt worts is graduated so that the divisions express pounds per barrel (32 gallons). The relation between degrees Bates (⫽b) and degrees Balling (⫽B) is shown by the following formula: B ⫽ 260b/(360 ⫹ b). See also below under Wine and Must Hydrometer. Salinometer. This hydrometer, which is used in the pickling and meat packing plants, is graduated to show percentage of saturation of a sodium chloride solution. An aqueous solution is completely saturated when it contains 26.4% pure sodium chloride. The range from 0% to 26.4% is divided into 100 parts, each division therefore representing 1% of saturation. In another type of salinometer, the degrees correspond to percentages of sodium chloride expressed in grams of sodium chloride per 100 mL of water. Sprayometer (Parrot and Stewart). This hydrometer which is used in determining the density of lime sulfur solutions has two scales; one scale is graduated from 0⬚ to 38⬚ Baume´ and the other scale is from 1.000 to 1.350 specific gravity. Tralle Hydrometer. See Alcoholometer above. Twaddell Hydrometer. This hydrometer, which is used only for liquids heavier than water, has a scale such that when the reading is multiplied by 5 and added to 1000 the resulting number is the specific gravity with reference to water as 1000. To convert specific gravity at 60⬚/60⬚F to Twaddell degrees, take the decimal portion of the specific gravity value and multiply it by 200; thus a specific gravity of 1.032 ⫽ 0.032 ⫻ 200 ⫽ 6.4⬚ Tw. See also special table for conversion to density and Baume´ scale. Wine and Must Hydrometer. This instrument has three scales. One scale shows readings of 0⬚ to 15⬚ Brix for sugar (see Brix Hydrometer above); another scale from 0⬚ to 15⬚ Tralle is used for sweet wines to indicate the percentage of alcohol by volume; and a third scale from 0⬚ to 20⬚ Tralle is used for tart wines to indicate the percentage of alcohol by volume. 2.1.2.2 Conversion of Specific Gravity at 25⬚/25⬚C to Density at any Temperature from 0⬚ to 40⬚C.* Liquids change volume with change in temperature, but the amount of this change, ␤ (coefficient of cubical expansion), varies widely with different liquids, and to some extent for the same liquid at different temperatures. The table below, which is calculated from the relationship: F␤ t ⫽

density of water at 25⬚C (⫽0.99705) 1 ⫺ ␤(25 ⫺ t)

* Cf. Dreisbach, Ind. Eng. Chem., Anal. Ed. 12:160 (1940).

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may be used to find d t, the density (weight of 1 mL) of a liquid at any temperature (t) between 0⬚ and 40⬚C if the specific gravity at 25⬚/25⬚C (S) and the coefficient of cubical expansion (␤) are known. Substitutions are made in the equations: d t ⫽ SF␤ t S⫽

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(2.2)

dt F␤ t

(2.3)

Factors (F␤ t) Density t⬚C ⫽ sp. gr. 25⬚/25⬚ ⫻ F␤ t ⬚C. *b ⫻ 103 1.3 1.2 1.1 1.0 0.9 0.8 0.7 0.6 0.5 0.

0

5

10

15

20

25

30

35

40

1.0306 1.0279 1.0253 1.0227 1.0200 1.0174 1.0148 1.0122 1.0097 1.0071

1.0237 1.0216 1.0195 1.0174 1.0153 1.0133 1.0113 1.0092 1.0072 1.0051

1.0169 1.0154 1.0138 1.0123 1.0107 1.0092 1.0077 1.0061 1.0046 1.0031

1.0102 1.0092 1.0082 1.0072 1.0060 1.0051 1.0041 1.0031 1.0021 1.0011

1.0036 1.0031 1.0026 1.0021 1.0016 1.0011 1.0006 1.0001 0.99958 0.99908

0.99705 0.99705 0.99705 0.99705 0.99705 0.99705 0.99705 0.99705 0.99705 0.99705

0.99065 0.9911 0.9916 0.9921 0.99262 0.9931 0.9935 0.9941 0.9944 0.9951

0.9843 0.9853 0.9963 0.9872 0.9882 0.98918 0.99015 0.9911 0.9921 0.9931

0.9780 0.9794 0.9809 0.98234 0.9838 0.9851 0.98672 0.9882 0.9897 0.9911

* ␤ ⫽ coefficient of cubical expansion.

Examples. All examples are based upon an assumed coefficient of cubical expansion, ␤, of 1.3 ⫻ 10⫺3. Example 1. To find the density of a liquid at 20⬚C, d 20, which has a specific gravity (S) of 1.250025 25 : From the table above F␤ t at 20⬚C ⫽ 1.0036. d 20 ⫽ d t ⫽ SF␤ t ⫽ 1.2500 ⫻ 1.0036 ⫽ 1.2545 Example 2. To find the density at 20⬚C (d 20) of a liquid which has a specific gravity of 1.2500174 : Since the density of water at 4⬚C is equal to 1, specific gravity at 17⬚/4⬚ ⫽ d17 ⫽ 1.2500. Substitution in Equation 3 with F␤ t at 17⬚C, by interpolation from the table, equal to 1.00756, gives Sp. gr. 25⬚/25⬚ ⫽ S ⫽ 1.2500 ⫼ 1.00756 Substitution of this value for S in Equation 2 with F␤ t at 20⬚C, from the table, equal to 1.0036, gives d 20 ⫽ d t ⫽ (1.2500 ⫼ 1.00756) ⫻ 1.0036 ⫽ 1.2451

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Example 3. To find the specific gravity at 20⬚/4⬚C of a liquid which has a specific gravity of 1.2500254 :

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Since the density of water at 4⬚C, is equal to 1, specific gravity 25⬚/4⬚ ⫽ d 25 ⫽ 1.2500; and, specific gravity 20⬚/4⬚ ⫽ d 20. Substitution in Equation 3, with d t ⫽ 1.2500; and, with F␤ t at 25⬚C, from the table, equal to 0.99705, gives Sp. gr. 25⬚/25⬚ ⫽ S ⫽ 1.2500 ⫼ 0.99705 Substitution of this value for S in Equation 2, with F␤ t at 20⬚C, from the table, equal to 1.0036, gives Sp. gr. 20⬚/4⬚ ⫽ d 20 ⫽ (1.2500 ⫼ 0.99705) ⫻ 1.0036 ⫽ 1.2582 Example 4. To find the density at 25⬚C of a liquid which has a specific gravity of 1.250015 15 : Since the density of water at 15⬚C ⫽ 0.99910, d15 ⫽ sp. gr. 15⬚/15⬚ ⫻ 0.99910 ⫽ 1.2500 ⫻ 0.99910 Substitution in Equation 3, with F␤ t at 15⬚C, from the table, equal to 1.0102, gives Sp. gr. 25⬚/25⬚ ⫽ S ⫽ (1.2500 ⫻ 0.99910) ⫼ 1.0102 Substitution of this value for S in Equation 2, with F␤ t at 25⬚, from the table, equal to 0.99705, gives d 26 ⫽ d t ⫽ (1.2500 ⫻ 0.99910 ⫼ 1.0102) ⫻ 0.99705 ⫽ 1.2326 2.1.3

Barometry and Barometric Corrections

In principle, the mercurial barometer balances a column of pure mercury against the weight of the atmosphere. The height of the column above the level of the mercury in the reservoir can be measured and serves as a direct index of atmospheric pressure. The space above the mercury in a barometer tube should be a Torricellian vacuum, perfect except for the practically negligible vapor pressure of mercury. The perfection of the vacuum is indicated by the sharpness of the click noted when the barometer tube is inclined. A barometer should be in a vertical position, suspended rather than fastened to a wall, and in a good light but not exposed to direct sunlight or too near a source of heat. The standard conditions for barometric measurements are 0⬚C and gravity as at 45⬚ latitude and sea level. There are numerous sources of error, but corrections for most of these are readily applied. Some of the corrections are very small, and their application may be questionable in view of the probably larger errors. The degree of consistency to be expected in careful measurements is about 0.13 mm with a 6.4-mm tube, increasing to 0.04 mm with a tube 12.7 mm in diameter. In reading a barometer of the Fortin type (the usual laboratory instrument for precision measurements), the procedure should be as follows: (1) Observe and record the temperature as indicated by the thermometer attached to the barometer. The temperature correction is very important and may be affected by heat from the observer’s body. (2) Set the mercury in the reservoir at zero level, so that the point of the pin above the mercury just touches the surface, making a barely noticeable dimple therein. Tap the tube at the top and verify the zero setting. (3) Bring the vernier down until the view at the light background is cut off at the highest point of the meniscus. Record the reading. The corrections to be made on the reading are as follows: (1) Temperature, to correct for the difference in thermal expansion of the mercury and the brass (or glass) to which the scale is attached.

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This correction converts the reading into the value of 0⬚C. The brass scale table is applicable to the Fortin barometer. See Tables 2.10 latitude-gravity correction, and 2.11 altitude-gravity correction, to compensate for differences in gravity, which would affect the height of the mercury column by variation in mass. If local gravity is unknown, an approximate correction may be made from the tables. Local values of gravity are often subject to irregularities which lead to errors even when the corrections here provided are made. It is, therefore, advisable to determine the local value of gravity, from which the correction can be effected in the following manner: Bt ⫽ Br ⫹

冉

g1 ⫺ g0 g0

冊

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⫻ Br

in which Bt and Br are the true and the observed heights of the barometer, respectively. g0 is standard gravity (980 665 cm · s⫺2), and g1 is the local gravity. It may be noted that for most localities, g1 is smaller than g0 , which makes the correction negative. These corrections compensate the reading to gravity at 45⬚ latitude and sea level. (3) Correction for capillary depression of the level of the meniscus. This varies with the tube diameter and actual height of the meniscus in a particular case. Some barometers are calibrated to allow for an average value of the latter and approximating the correction. See table. (4) Correction for vapor pressure of mercury. This correction is usually negligible, being only 0.001 mm at 20⬚C and 0.006 mm at 40⬚C. This correction is added. See table of vapor pressure of mercury. The corrections above do not apply to aneroid barometers. These instruments should be calibrated at regular intervals by checking them against a corrected mercurial barometer. For records on weather maps, meteorologists customarily correct barometer readings to sea level, and some barometers may be calibrated accordingly. Such instruments are not suitable for laboratory use where true pressure under standard conditions is required. Scale corrections should be specified in the maker’s instructions with the instrument, and are also indicated by the lack of correspondence between a gauge mark usually placed exactly 76.2 cm from the zero point and the 76.2-cm scale graduation.

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TABLE 2.9 Barometer Temperature Correction— Metric Units The values in the table below are to be subtracted from the observed readings to correct for the difference in the expansion of the mercury and the glass scale at different temperatures. A. Glass scale Observed barometer height in millimeters 740 750 760

700

730

Temp. ⬚C.

770

800

mm.

mm.

mm.

mm.

mm.

mm.

mm.

0 1 2 3 4

0.00 0.12 0.24 0.36 0.49

0.00 0.13 0.25 0.38 0.51

0.00 0.13 0.26 0.38 0.51

0.00 0.13 0.26 0.39 0.52

0.00 0.13 0.26 0.40 0.53

0.00 0.13 0.27 0.40 0.53

0.00 0.14 0.27 0.42 0.55

5 6 7 8 9

0.61 0.73 0.85 0.97 1.09

0.63 0.76 0.89 1.01 1.14

0.64 0.77 0.90 1.03 1.15

0.65 0.78 0.91 1.04 1.17

0.66 0.79 0.92 1.05 1.18

0.67 0.80 0.93 1.07 1.20

0.69 0.83 0.97 1.11 1.25

10 11 12 13 14

1.21 1.33 1.45 1.58 1.70

1.26 1.39 1.52 1.64 1.77

1.28 1.41 1.54 1.67 1.79

1.30 1.43 1.56 1.69 1.82

1.32 1.45 1.58 1.71 1.84

1.33 1.47 1.60 1.73 1.87

1.39 1.52 1.66 1.80 1.94

15 16 17 18 19

1.82 1.94 2.06 2.18 2.30

1.90 2.02 2.15 2.27 2.40

1.92 2.05 2.18 2.30 2.43

1.95 2.08 2.21 2.33 2.46

1.97 2.10 2.23 2.37 2.50

2.00 2.13 2.26 2.40 2.53

2.08 2.21 2.35 2.49 2.63

20 21 22 23 24

2.42 2.54 2.66 2.78 2.90

2.52 2.65 2.78 2.90 3.03

2.56 2.69 2.81 2.94 3.07

2.59 2.72 2.85 2.98 3.11

2.63 2.76 2.89 3.02 3.15

2.66 2.79 2.93 3.06 3.19

2.77 2.90 3.04 3.18 3.32

25 26 27 28 29

3.02 3.14 3.26 3.38 3.50

3.15 3.28 3.40 3.53 3.65

3.20 3.32 3.45 3.58 3.70

3.24 3.37 3.50 3.63 3.75

3.28 3.41 3.54 3.67 3.80

3.32 3.46 3.59 3.72 3.85

3.45 3.59 3.73 3.87 4.00

30 31 32 33 34 35

3.62 3.74 3.86 3.98 4.10 4.22

3.78 3.90 4.03 4.15 4.28 4.40

3.83 3.96 4.08 4.21 4.34 4.47

3.88 4.01 4.14 4.27 4.40 4.53

3.93 4.06 4.20 4.33 4.46 4.59

3.99 4.12 4.25 4.38 4.51 4.65

4.14 4.28 4.42 4.55 4.69 4.83

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TABLE 2.9 Barometer Temperature Correction— Metric Units (Continued) The values in the table below are to be subtracted from the observed readings to correct for the difference in the expansion of the mercury and the glass scale at different temperatures. B. Brass scale Observed barometer height in millimeters 660 670 680

640

650

Temp. ⬚C.

690

700

mm.

mm.

mm.

mm.

mm.

mm.

mm.

0 1 2 3 4

0.00 0.10 0.21 0.31 0.42

0.00 0.11 0.21 0.32 0.42

0.00 0.11 0.22 0.32 0.43

0.00 0.11 0.22 0.33 0.44

0.00 0.11 0.22 0.33 0.44

0.00 0.11 0.23 0.34 0.45

0.00 0.11 0.23 0.34 0.46

5 6 7 8 9

0.52 0.63 0.73 0.84 0.94

0.53 0.64 0.74 0.85 0.95

0.54 0.65 0.75 0.86 0.97

0.55 0.66 0.76 0.87 0.98

0.55 0.66 0.78 0.89 1.00

0.56 0.67 0.79 0.90 1.01

0.57 0.68 0.80 0.91 1.03

10 11 12 13 14

1.04 1.15 1.25 1.35 1.46

1.06 1.16 1.27 1.38 1.48

1.07 1.18 1.29 1.40 1.50

1.09 1.20 1.31 1.42 1.53

1.11 1.22 1.33 1.44 1.55

1.12 1.24 1.35 1.46 1.57

1.14 1.25 1.37 1.48 1.59

15 16 17 18 19

1.56 1.67 1.77 1.87 1.98

1.59 1.69 1.80 1.90 2.01

1.61 1.72 1.82 1.93 2.04

1.64 1.74 1.85 1.96 2.07

1.66 1.77 1.88 1.99 2.10

1.68 1.80 1.91 2.02 2.13

1.71 1.82 1.94 2.05 2.16

20 21 22 23 24

2.08 2.18 2.29 2.39 2.49

2.11 2.22 2.32 2.43 2.53

2.15 2.25 2.36 2.47 2.57

2.18 2.29 2.40 2.50 2.61

2.21 2.32 2.43 2.54 2.65

2.24 2.35 2.47 2.58 2.69

2.28 2.39 2.50 2.62 2.73

25 26 27 28 29

2.60 2.70 2.81 2.91 3.01

2.64 2.74 2.85 2.95 3.06

2.68 2.79 2.89 3.00 3.11

2.72 2.83 2.94 3.05 3.15

2.76 2.87 2.98 3.09 3.20

2.80 2.91 3.02 3.14 3.25

2.84 2.96 3.07 3.18 3.29

30 31 32 33 34 35

3.12 3.22 3.32 3.42 3.53 3.63

3.16 3.27 3.37 3.48 3.58 3.69

3.21 3.32 3.43 3.53 3.64 3.74

3.26 3.37 3.48 3.59 3.69 3.80

3.31 3.42 3.53 3.64 3.75 3.86

3.36 3.47 3.58 3.69 3.80 3.91

3.41 3.52 3.63 3.75 3.86 3.97

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TABLE 2.9 Barometer Temperature Correction— Metric Units (Continued) B. Brass scale (continued)

710

720

Observed barometer height in millimeters 730 740 750 760

770

780

mm.

mm.

mm.

mm.

mm.

mm.

mm.

mm.

Temp. ⬚C.

0.00 0.12 0.23 0.35 0.46

0.00 0.12 0.23 0.35 0.47

0.00 0.12 0.24 0.36 0.48

0.00 0.12 0.24 0.36 0.48

0.00 0.12 0.24 0.37 0.49

0.00 0.12 0.25 0.37 0.50

0.00 0.13 0.25 0.38 0.50

0.00 0.13 0.25 0.38 0.51

0 1 2 3 4

0.58 0.69 0.81 0.93 1.04

0.59 0.70 0.82 0.94 1.06

0.59 0.71 0.83 0.95 1.07

0.60 0.72 0.84 0.96 1.08

0.61 0.73 0.86 0.98 1.10

0.62 0.74 0.87 0.99 1.11

0.63 0.75 0.88 1.00 1.13

0.64 0.76 0.89 1.02 1.14

5 6 7 8 9

1.16 1.27 1.39 1.50 1.62

1.17 1.29 1.41 1.52 1.64

1.19 1.31 1.43 1.54 1.66

1.21 1.33 1.45 1.57 1.69

1.22 1.34 1.47 1.59 1.71

1.24 1.36 1.48 1.61 1.73

1.25 1.38 1.50 1.63 1.75

1.27 1.40 1.52 1.65 1.78

10 11 12 13 14

1.73 1.85 1.96 2.08 2.19

1.76 1.87 1.99 2.11 2.22

1.78 1.90 2.02 2.14 2.25

1.81 1.93 2.05 2.17 2.29

1.83 1.95 2.07 2.20 2.32

1.85 1.98 2.10 2.22 2.35

1.88 2.00 2.13 2.25 2.38

1.90 2.03 2.16 2.28 2.41

15 16 17 18 19

2.31 2.42 2.54 2.65 2.77

2.34 2.46 2.57 2.69 2.81

2.37 2.49 2.61 2.73 2.85

2.41 2.53 2.65 2.77 2.88

2.44 2.56 2.68 2.80 2.92

2.47 2.59 2.72 2.84 2.96

2.50 2.63 2.75 2.88 3.00

2.54 2.66 2.79 2.91 3.04

20 21 22 23 24

2.88 3.00 3.11 3.23 3.34

2.92 3.04 3.16 3.27 3.39

2.96 3.08 3.20 3.32 3.44

3.00 3.12 3.24 3.36 3.48

3.05 3.17 3.29 3.41 3.53

3.09 3.21 3.33 3.45 3.58

3.13 3.25 3.38 3.50 3.62

3.17 3.29 3.42 3.54 3.67

25 26 27 28 29

3.46 3.57 3.68 3.80 3.91 4.03

3.50 3.62 3.74 3.85 3.97 4.09

3.55 3.67 3.79 3.91 4.02 4.14

3.60 3.72 3.84 3.96 4.08 4.20

3.65 3.77 3.89 4.01 4.13 4.26

3.70 3.82 3.94 4.07 4.19 4.31

3.75 3.87 4.00 4.12 4.24 4.37

3.80 3.92 4.05 4.17 4.30 4.43

30 31 32 33 34 35

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TABLE 2.9 Barometer Temperature Correction— Metric Units (Continued) C. Correction of a barometer for capillarity (Smithsonian Tables)

Diameter of tube, millimeters

0.4

4 5 6 7 8 9 10 11 12 13

0.83 0.47 0.27 0.18 . . . . . . . . . . . . . . . . . . . . . . . .

0.6

Height of meniscus in millimeters 0.8 1.0 1.2 1.4

1.6

1.8

. . . . . . . . 1.43 0.97 0.65 0.46 0.33 0.24 0.18 0.13

. . . . . . . . . . . . 1.13 0.77 0.52 0.37 0.27 0.19 0.14

Correction to be added in millimeters 1.22 0.65 0.41 0.28 0.20 0.15 . . . . . . . . . . . . . . . .

1.54 0.86 0.56 0.40 0.29 0.21 0.15 0.10 0.07 0.04

1.98 1.19 0.78 0.53 0.38 0.28 0.20 0.14 0.10 0.07

2.37 1.45 0.98 0.67 0.46 0.33 0.25 0.18 0.13 0.10

. . . . 1.80 1.21 0.82 0.56 0.40 0.29 0.21 0.15 0.12

TABLE 2.10 Barometric Latitude-Gravity Table— Metric Units Smithsonian Tables. The values in the table below are to be subtracted from the barometric reading for latitudes from 0 to 45⬚ inclusive, and are to be added from 46 to 90⬚. Barometer readings, millimeters 720 740

Deg. Lat.

680

700

760

780

mm.

mm.

mm.

mm.

mm.

mm.

0 5 10 15 20

1.82 1.79 1.71 1.58 1.40

1.87 1.85 1.76 1.63 1.44

1.93 1.90 1.81 1.67 1.49

1.98 1.95 1.86 1.72 1.53

2.04 2.00 1.92 1.77 1.57

2.09 2.06 1.97 1.81 1.61

21 22 23 24 25

1.36 1.32 1.28 1.23 1.18

1.40 1.36 1.31 1.27 1.22

1.44 1.40 1.35 1.30 1.25

1.48 1.44 1.39 1.34 1.29

1.52 1.48 1.43 1.37 1.32

1.56 1.51 1.46 1.41 1.36

26 27 28 29 30

1.13 1.08 1.03 0.98 0.93

1.17 1.12 1.06 1.01 0.95

1.20 1.15 1.09 1.04 0.98

1.23 1.18 1.12 1.07 1.01

1.27 1.21 1.15 1.10 1.04

1.30 1.24 1.18 1.12 1.06

31 32 33 34 35

0.87 0.82 0.76 0.70 0.64

0.90 0.84 0.78 0.72 0.66

0.92 0.86 0.80 0.74 0.68

0.95 0.89 0.83 0.76 0.70

0.98 0.91 0.85 0.79 0.72

1.00 0.94 0.87 0.81 0.74

36 37 38

0.58 0.52 0.46

0.60 0.54 0.48

0.62 0.56 0.49

0.64 0.57 0.51

0.65 0.59 0.52

0.67 0.60 0.53

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TABLE 2.10 Barometric Latitude-Gravity Table— Metric Units (Continued) Barometer readings, millimeters 720 740

Deg. Lat.

680

700

760

780

mm.

mm.

mm.

mm.

mm.

mm.

39 40

0.40 0.34

0.42 0.35

0.43 0.36

0.44 0.37

0.45 0.38

0.46 0.39

41 42 43 44 45

0.28 0.22 0.16 0.09 0.03

0.29 0.22 0.16 0.10 0.03

0.30 0.23 0.16 0.10 0.03

0.30 0.24 0.17 0.10 0.03

0.31 0.24 0.17 0.10 0.03

0.32 0.25 0.18 0.11 0.04

46 47 48 49 50

0.03 0.09 0.16 0.22 0.28

0.03 0.10 0.16 0.23 0.29

0.03 0.10 0.17 0.23 0.30

0.03 0.10 0.17 0.24 0.31

0.04 0.10 0.18 0.25 0.31

0.04 0.11 0.18 0.25 0.32

51 52 53 54 55

0.34 0.40 0.46 0.52 0.58

0.35 0.42 0.48 0.54 0.60

0.36 0.43 0.49 0.56 0.62

0.37 0.44 0.51 0.57 0.64

0.38 0.45 0.52 0.59 0.65

0.39 0.46 0.53 0.60 0.67

56 57 58 59 60

0.64 0.70 0.76 0.81 0.87

0.66 0.72 0.78 0.84 0.89

0.68 0.74 0.80 0.86 0.92

0.70 0.76 0.82 0.89 0.94

0.72 0.78 0.85 0.91 0.97

0.74 0.80 0.87 0.93 1.00

61 62 63 64 65

0.92 0.97 1.03 1.08 1.13

0.95 1.00 1.06 1.11 1.16

0.98 1.02 1.09 1.14 1.19

1.00 1.05 1.12 1.17 1.22

1.03 1.08 1.15 1.20 1.26

1.06 1.11 1.18 1.23 1.29

66 67 68 69 70

1.17 1.22 1.26 1.31 1.35

1.21 1.25 1.30 1.34 1.39

1.24 1.29 1.34 1.38 1.43

1.28 1.33 1.37 1.42 1.47

1.31 1.36 1.41 1.46 1.51

1.35 1.40 1.45 1.50 1.55

72 75 80 85 90

1.42 1.53 1.66 1.74 1.77

1.47 1.57 1.71 1.79 1.82

1.51 1.62 1.76 1.84 1.87

1.55 1.66 1.81 1.90 1.93

1.59 1.71 1.86 1.95 1.98

1.63 1.75 1.90 2.00 2.03

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TABLE 2.11 Barometric Correction for Gravity— Metric Units The values in the table below are to be subtracted from the readings taken on a mercurial barometer to correct for the decrease in gravity with increase in altitude. Observed barometer height in millimeters

Height above sealevel meters

400

450

500

550

600

650

700

750

800

mm.

mm.

mm.

mm.

mm.

mm.

mm.

mm.

mm.

100 200 300 400 500

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

0.02 0.04 0.07 0.09 0.11

0.02 0.05 0.07 0.10 0.12

0.02 0.05 0.07 0.10 0.13

600 700 800 900 1000

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... 0.18

.... .... .... .... 0.19

0.12 0.14 0.16 0.18 0.20

0.13 0.15 0.18 0.20 0.22

0.14 0.16 0.19 0.22 0.24

.... .... .... .... ....

1100 1200 1300 1400 1500

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... 0.24

0.19 0.21 0.22 0.24 0.26

0.21 0.23 0.24 0.26 0.28

0.22 0.24 0.26 0.28 0.30

0.24 0.26 0.29 0.31 0.33

.... .... .... .... ....

.... .... .... .... ....

1600 1700 1800 1900 2000

.... .... .... .... ....

.... .... .... .... 0.28

0.25 0.27 0.28 0.30 0.31

0.28 0.30 0.31 0.33 0.34

0.30 0.32 0.34 0.36 0.38

0.32 0.34 0.36 0.39 0.41

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

2100 2200 2300 2400 2500

.... .... .... .... 0.31

0.30 0.31 0.32 0.34 0.35

0.33 0.35 0.36 0.38 0.39

0.36 0.38 0.40 0.42 0.43

0.40 0.41 0.43 0.45 0.47

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

2600 2800 3000 3200 3400

0.33 0.35 0.38 0.40 0.43

0.37 0.40 0.42 0.46 0.48

0.41 0.44 0.47 .... ....

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

.... .... .... .... ....

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TABLE 2.12 Reduction of the Barometer to Sea Level— Metric Units A barometer located at an elevation above sea level will show a reading lower than a barometer at sea level by an amount approximately 2.5 mm (0.1 in) for each 30.5 m (100 ft) of elevation. A closer approximation can be made by reference to the following tables, which take into account (1) the effect of altitude of the station at which the barometer is read, (2) the mean temperature of the air column extending from the station down to sea level, (3) the latitude of the station at which the barometer is read, and (4) the reading of the barometer corrected for its temperature, a correction which is applied only to mercurial barometers since the aneroid barometers are compensated for temperature effects. Example. A barometer which has been corrected for its temperature reads 650 mm at a station whose altitude is 1350 m above sea level and at a latitude of 30⬚. The mean temperature (outdoor temperature) at the station is 20⬚C. Table A (metric units) gives for these conditions a temperature-altitude factor of . . . . . . . . . . . . . . . . . . The Latitude Factor Table gives for 135.2 at 30⬚ lat. a correction of . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Therefore, the corrected value of the temperature-altitude factor is . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Entering Table B (metric units), with a temperature-altitude factor of 135.37 and a barometric reading of 650 mm (corrected for temperature), the correction is found to be . . . . . . . . . . . . . . . . . . . . . . . . . . Accordingly the barometric reading reduced to sea level is 650 ⫹ 109.6 ⫽ 759.6 mm.

135.2 ⫹0.17 135.37 109.6

Latitude Factor– English or Metric Units. For latitudes 0⬚– 45⬚ add the latitude factor, for 45⬚– 90⬚ subtract the latitude factor, from the values obtained in Table A. Temp.— Alt. Factor From Table A

Latitude 0⬚

10⬚

20⬚

30⬚

45⬚

50 100 150 200 250 300 350

0.1 0.3 0.4 0.5 0.7 0.8 0.9

0.1 0.3 0.4 0.5 0.6 0.8 0.9

0.1 0.2 0.3 0.4 0.5 0.6 0.7

0.1 0.1 0.2 0.3 0.3 0.4 0.5

0.0 0.0 0.0 0.0 0.0 0.0 0.0

90⬚

80⬚

70⬚

60⬚

45⬚

A. Values of the temperature-altitude factor for use in Table B.* Altitude in Meters

Mean Temperature of Air Column in Centigrade Degrees ⫺16⬚

⫺8⬚

⫺4⬚

0⬚

6⬚

10⬚

14⬚

18⬚

20⬚

22⬚

26⬚

10 50 100 150

1.2 5.8 11.5 17.3

1.1 5.6 11.2 16.7

1.1 5.5 11.0 16.5

1.1 5.4 10.8 16.2

1.1 5.3 10.6 15.9

1.0 5.2 10.4 15.6

1.0 5.1 10.3 15.4

1.0 5.0 10.1 15.1

1.0 5.0 10.0 15.0

1.0 5.0 9.9 14.9

1.0 4.9 9.8 14.7

200 250 300 350 400

23.0 28.8 34.5 40.3 46.0

22.3 27.9 33.5 39.0 44.6

22.0 27.5 33.0 38.5 43.9

21.6 27.0 32.5 37.9 43.3

21.1 26.4 31.7 37.0 42.3

20.8 26.0 31.2 36.4 41.6

20.5 25.6 30.7 35.9 41.0

20.2 25.2 30.3 35.3 40.4

20.0 25.0 30.1 35.1 40.1

19.9 24.9 29.8 34.8 39.8

19.6 24.5 29.4 34.3 39.2

450 500 550 600 650

51.8 57.5 63.3 69.0 74.8

51.3 55.8 61.4 66.9 72.5

49.4 54.9 60.4 65.9 71.4

48.7 54.1 59.5 64.9 70.3

47.6 52.9 58.1 63.4 68.7

46.8 52.0 57.2 62.4 67.6

46.1 51.2 56.4 61.5 66.6

45.4 50.5 55.5 60.6 65.6

45.1 50.1 55.1 60.1 65.1

44.8 49.7 54.7 59.7 64.6

44.1 49.0 53.9 58.8 63.7

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TABLE 2.12 Reduction of the Barometer to Sea Level— Metric Units (Continued) Altitude in Meters

Mean Temperature of Air Column in Centigrade Degrees ⫺16⬚

⫺8⬚

⫺4⬚

0⬚

6⬚

10⬚

14⬚

18⬚

20⬚

22⬚

26⬚

700 750 800 850 900

80.6 86.3 92.1 97.8 103.6

78.1 83.7 89.2 94.8 100.4

76.9 82.4 87.9 93.4 98.9

75.7 81.1 86.5 92.0 97.4

74.0 79.3 84.6 89.8 95.1

72.9 78.1 83.3 88.5 93.7

71.7 76.9 82.0 87.1 92.2

70.7 75.7 80.8 85.8 90.8

70.1 75.1 80.1 85.2 90.2

69.6 74.6 79.6 84.5 89.5

68.6 73.5 78.4 83.3 88.2

950 1000 1050 1100 1150

109.3 115.1 120.8 126.6 132.3

106.0 111.5 117.1 122.7 128.3

104.4 109.8 115.3 120.8 126.3

102.8 108.2 113.6 119.0 124.4

100.4 105.7 111.0 116.3 121.6

98.9 104.1 109.3 114.5 119.7

97.4 102.5 107.6 112.7 117.9

95.9 100.9 106.0 111.0 116.1

95.2 100.2 105.2 110.2 115.2

94.5 99.4 104.4 109.4 114.4

93.1 98.0 102.9 107.8 112.7

1200 1250 1300 1350 1400

138.1 143.8 149.6 155.3 161.1

133.8 139.4 145.0 150.6 156.2

131.8 137.3 142.8 148.3 153.8

129.8 135.2 140.6 146.0 151.4

126.8 132.1 137.4 142.7 148.0

124.9 130.1 135.3 140.5 145.7

123.0 128.1 133.2 138.4 143.5

121.1 126.2 131.2 136.3 141.3

120.2 125.2 130.2 135.2 140.2

119.3 124.3 129.3 134.2 139.2

117.6 122.5 127.4 132.3 137.2

1450 1500 1550 1600 1650

166.8 172.6 178.3 184.1 189.8

161.7 167.3 172.9 178.5 184.0

159.3 164.8 170.2 175.7 181.2

156.8 162.3 167.7 173.1 178.5

153.3 158.5 163.8 169.1 174.4

150.9 156.1 161.3 166.5 171.7

148.6 153.7 158.8 164.0 169.1

146.4 151.4 156.4 161.5 166.5

145.3 150.3 155.3 160.3 165.3

144.2 149.1 154.1 159.1 164.1

142.1 147.0 151.8 156.7 161.6

1700 1750 1800 1850 1900

195.6 201.4 207.1 212.9 218.6

189.6 195.2 200.8 206.3 211.9

186.7 192.2 197.7 203.2 208.7

183.9 189.3 194.7 200.1 205.5

179.7 185.0 190.2 195.5 200.8

176.9 182.1 187.3 192.5 197.7

174.2 179.3 184.5 189.6 194.7

171.6 176.6 181.7 186.7 191.8

170.3 175.3 180.3 185.3 190.3

169.0 174.0 179.0 183.9 188.9

166.5 171.4 176.3 181.2 186.1

1950 2000 2050 2100 2150

224.4 230.1 235.9 241.6 247.4

217.5 223.0 228.6 234.2 239.8

214.2 219.7 225.1 230.6 236.1

210.9 216.3 221.7 227.1 232.5

206.1 211.4 216.7 221.9 227.2

202.9 208.1 213.3 218.5 223.7

199.8 204.9 210.1 215.2 220.3

196.8 201.9 206.9 211.9 217.0

195.3 200.3 205.3 210.4 215.4

193.9 198.8 203.8 208.8 213.8

191.0 195.0 200.8 205.7 210.6

2200 2250 2300 2350 2400

253.1 258.9 264.6 270.4 276.1

245.4 250.9 256.5 262.1 267.7

241.6 247.1 252.6 258.1 263.6

237.9 243.4 248.8 254.2 259.6

232.5 237.8 243.1 248.3 253.6

228.9 234.1 239.3 244.5 249.7

225.4 230.6 235.7 240.8 245.9

222.0 227.1 232.1 237.2 242.2

220.4 225.4 230.4 235.4 240.4

218.7 223.7 228.7 233.6 238.6

215.5 220.4 225.3 230.2 235.1

2450 2500 2550 2600 2650

281.9 287.6 293.4 299.1 304.9

273.2 278.8 284.4 290.0 295.5

269.1 274.5 280.0 285.5 291.0

265.0 270.4 275.8 281.2 286.6

258.9 264.2 269.5 274.8 280.0

254.9 260.1 265.3 270.5 275.7

251.0 256.2 261.3 266.4 271.5

247.3 252.3 257.3 262.4 267.4

245.4 250.4 255.4 260.4 265.4

243.6 248.5 253.5 258.5 263.4

240.0 244.9 249.8 254.7 259.6

2700 2750 2800 2850 2900

310.6 316.4 322.1 327.9 333.6

301.1 306.7 312.3 317.8 323.4

296.5 302.0 307.5 313.0 318.4

292.0 297.4 302.8 308.2 313.6

285.3 290.6 295.9 301.2 306.4

280.9 286.1 291.3 296.5 301.7

276.6 281.8 286.9 292.0 297.1

272.5 277.5 282.6 287.6 292.6

270.4 275.4 280.4 285.4 290.4

268.4 273.4 278.3 283.3 288.3

264.5 269.4 274.3 279.2 284.1

2950 3000

339.4 345.1

329.0 334.5

323.9 329.4

319.0 324.4

311.7 317.0

306.9 312.1

302.2 307.4

297.7 302.7

295.5 300.5

293.3 298.2

289.0 293.8

* From Smithsonian Meteorological Tables, 3d ed., 1907.

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TABLE 2.12 Reduction of the Barometer to Sea Level— Metric Units (Continued) B. Values in millimeters to be added.* Temp. — Alt. Factor 1 5 10 15 20 25 30 35 40 45

50 55 60 65 70 75 80 85 90 95

100 105 110 115 120 125 130 135 140 145

150 155 160 165 170 175 180 185 190 195

Barometer Reading in Millimeters 790

770

750

730

710

690

670

0.9 4.6 9.1 13.8 18.4

0.9 4.4 8.9 13.4 17.9 22.5 27.1 31.7 36.3

0.9 4.3 8.7 13.1 17.5 21.9 26.4 30.8 35.3 39.9

0.8 4.2 8.5 12.7 17.0 21.3 25.7 30.0 34.4 38.8

0.8 4.1 8.2 12.4 16.5 20.7 25.0 29.2 33.5 37.8

0.8 4.0 8.0 12.0 16.1 20.1 24.2 28.4 32.5 36.7

31.6 35.6

750

730

710

690

670

650

630

44.4 49.0 53.6 58.3

43.3 47.7 52.2 56.7 61.3 65.8 70.4 75.0

42.1 46.4 50.8 55.2 59.6 64.0 68.5 73.0 77.5 82.1

40.9 45.1 49.3 53.6 57.9 62.2 66.6 70.9 75.3 79.7

39.7 43.8 47.9 52.1 56.2 60.4 64.6 68.9 73.1 77.4

62.7 66.8 71.0 75.1

60.8 64.8 68.8 72.8

710

690

670

650

630

610

86.6 91.2 95.9 100.5

84.2 88.7 93.2 97.7 102.2 106.8 111.4 116.0 120.7

81.8 86.1 90.5 94.8 99.3 103.7 108.2 112.7 117.2 121.7

79.3 83.5 87.8 92.0 96.3 100.6 104.9 109.3 113.7 118.1

76.9 81.0 85.1 89.2 93.3 97.5 101.7 105.9 110.2 114.5

94.4 98.5 102.6 106.7 110.8

670

650

630

610

590

570

126.3 130.9 135.5 140.2

122.5 127.0 131.5 136.0 140.5 145.1 149.7 154.3 158.9

118.8 123.1 127.4 131.8 136.2 140.6 145.1 149.5 154.0 158.6

115.0 119.2 123.4 127.6 131.9 136.2 140.5 144.8 149.2 153.5

127.5 131.7 135.9 140.0 144.3 148.5

123.2 127.2 131.3 135.3 139.4 143.5

* From Smithsonian Meteorological Tables, 3d ed., 1907.

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TABLE 2.12 Reduction of the Barometer to Sea Level— Metric Units (Continued) B. Values in millimeters to be added.* Temp. — Alt. Factor 200 205 210 215 220 225 230 235 240 245

250 255 260 265 270 275 280 285 290 295

300 305 310 315 320 325 330 335 340 345

Barometer Reading in Millimeters 630

610

590

570

550

530

163.1 167.7 172.3 176.9

157.9 162.4 166.8 171.3 175.8 180.4 184.9 189.5 194.1 198.8

152.8 157.1 161.4 165.7 170.1 174.5 178.9 183.3 187.8 192.3

147.6 151.7 155.9 160.1 164.3 168.5 172.8 177.1 181.4 185.7

154.5 158.5 162.6 166.7 170.9 175.0 179.2

148.9 152.8 156.7 160.7 164.7 168.7 172.7

590

570

550

530

510

196.8 201.3 205.9 210.5 215.1 219.8

190.1 194.5 198.9 203.3 207.8 212.3 216.8 221.4 225.9 230.5

183.4 187.7 191.9 196.2 200.5 204.9 209.2 213.6 218.0 222.4

176.8 180.8 185.0 189.1 193.2 197.4 201.6 205.8 210.1 214.3

178.0 181.9 185.9 190.0 194.0 198.1 202.1 206.3

570

550

530

510

490

235.1 239.8

226.9 231.4 235.9 240.4 245.0 249.6 254.2 258.8 263.5

218.6 223.0 227.3 231.7 236.1 240.5 244.9 249.4 253.9 258.4

210.4 214.6 218.7 222.9 227.2 231.4 235.7 240.0 244.4 248.7

206.1 210.1 214.2 218.3 222.4 226.5 230.6 234.8 238.9

* From Smithsonian Meteorological Tables, 3d ed., 1907.

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TABLE 2.13 Viscosity Conversion Table Centistokes to Saybolt, Redwood, and Engler units. Poise ⫽ cgs unit of absolute viscosity

Centipoise ⫽ 0.01 poise

Stoke ⫽ cgs unit of kinematic viscosity

Centistoke ⫽ 0.01 stoke

Centipoises ⫽ centistokes ⫻ density (at temperature under consideration) Reyn (1 lb · s per sq in) ⫽ 69 ⫻ 105 centpoises Cf. Jour. Inst. Pet. Tech., Vol. 22, p. 21 (1936); Reports of A. S. T. M. Committee D-2, 1936 and 1937. The values of Saybolt Universal Viscosity at 100⬚F and at 210⬚F are taken directly from the comprehensive ASTM Viscosity Table, Special Technical Publication No. 43A (1953) by permission of the publishers, American Society for Testing Materials, 1916 Race St., Philadelphia 3, Pa.

Centistokes

100⬚F.

130⬚F.

210⬚F.

70⬚F.

140⬚F.

200⬚F.

Engler Degrees at all Temps.

2.0 3.0 4.0 5.0 6.0 7.0 8.0 9.0 10.0 11.0 12.0 14.0 16.0 18.0 20.0 22.0 24.0 26.0 28.0 30.0 32.0 34.0 36.0 38.0 40.0 42.0 44.0 46.0 48.0 50.0 60.0 70.0 80.0 90.0 100.0*

32.62 36.03 39.14 42.35 45.56 48.77 52.09 55.50 58.91 62.43 66.04 73.57 81.30 89.44 97.77 106.4 115.0 123.7 132.5 141.3 150.2 159.2 168.2 177.3 186.3 195.3 204.4 213.7 222.9 232.1 278.3 324.4 370.8 417.1 463.5

32.68 36.10 39.22 42.43 45.65 48.86 52.19 55.61 59.02 62.55 66.17 73.71 81.46 89.61 97.96 106.6 115.2 123.9 132.8 141.6 150.5 159.5 168.5 177.6 186.7 195.7 204.8 214.1 223.3 232.5 278.8 325.0 371.5 417.9 464.4

32.85 36.28 39.41 42.65 45.88 49.11 52.45 55.89 59.32 62.86 66.50 74.09 81.87 90.06 98.45 107.1 115.8 124.5 133.4 142.3 151.2 160.3 169.4 178.5 187.6 196.7 205.9 215.2 224.5 233.8 280.2 326.7 373.4 420.0 466.7

30.2 32.7 35.3 37.9 40.5 43.2 46.0 48.9 51.7 54.8 57.9 64.4 71.0 77.9 85.0 92.4 99.9 107.5 115.3 123.1 131.0 138.9 146.9 155.0 163.0 171.0 179.1 187.1 195.2 203.3 243.5 283.9 323.9 364.4 404.9

31.0 33.5 36.0 38.5 41.0 43.7 46.4 49.1 52.0 55.0 58.1 64.6 71.4 78.5 85.8 93.3 100.9 108.6 116.5 124.4 132.3 140.2 148.2 156.2 164.3 172.3 180.4 188.5 196.6 204.7 245.3 286.0 326.6 367.4 408.2

31.2 33.7 36.3 38.9 41.5 44.2 46.9 49.7 52.6 55.6 58.8 65.3 72.2 79.4 86.9 94.5 102.2 110.0 118.0 126.0 134.1 142.2 150.3 158.3 166.7 175.0 183.3 191.7 200.0 208.3 250.0 291.7 333.4 375.0 416.7

1.14 1.22 1.31 1.40 1.48 1.56 1.65 1.75 1.84 1.93 2.02 2.22 2.43 2.64 2.87 3.10 3.34 3.58 3.82 4.07 4.32 4.57 4.83 5.08 5.34 5.59 5.85 6.11 6.37 6.63 7.90 9.21 10.53 11.84 13.16

Saybolt Universal Viscosity at

Redwood Seconds at

* At higher values use the same ratio as above for 100 centistokes; e.g., 102 centistokes ⫽ 102 ⫻ 4.635 Saybolt seconds at 100⬚F. To obtain the Saybolt Universal viscosity equivalent to a kinematic viscosity determined at t⬚F., multiply the equivalent Saybolt Universal viscosity at 100⬚F. by 1 ⫹ (t ⫺ 100) 0.000064; e.g., 10 centistokes at 210⬚F are equivalent to 58.91 ⫻ 1.0070, or 59.32 Saybolt Universal Viscosity at 210⬚F.

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TABLE 2.14 Conversion of Weighings in Air to Weighings in Vacuo If the mass of a substance in air is m f , its density ␳m , the density of weights used in making the weighing ␳w , and the density* of air ␳a , the true mass of the substance in vacuo, mvac , is mvac ⫽ m f ⫹ ␳a m f

冉

1 1 ⫺ ␳m ␳w

冊

For most purposes it is sufficient to assume a density of 8.4 for brass weights, and a density of 0.0012 for air under ordinary conditions. The equation then becomes m vac ⫽ m f ⫹ 0.0012m f

冉

1 1 ⫺ ␳m 8.4

冊

The table which follows gives the values of k (buoyancy reduction factor), which is the correction necessary because of the buoyant effect of the air upon the object weighed; the table is computed for air with the density of 0.0012; m is the weight in grams of the object when weighed in air; weight of object reduced to “in vacuo” ⫽ m ⫹ km/1000. Buoyancy reduction factor, k Density of object weighed

Brass weights, density ⫽ 8.4

Pt or Pt-Ir weights, density ⫽ 21.5

Al or quartz weights, density ⫽ 2.7

Gold weights, density ⫽ 17

0.2 0.3 0.4 0.5 0.6

5.89 3.87 2.87 2.26 1.86

5.98 3.96 2.95 2.35 1.95

5.58 3.56 2.55 1.95 1.55

5.97 3.95 2.94 2.34 1.93

0.7 0.75 0.80 0.82 0.84

1.57 1.46 1.36 1.32 1.29

1.66 1.55 1.45 1.41 1.37

1.26 1.15 1.05 1.01 0.98

1.65 1.53 1.43 1.39 1.36

0.86 0.88 0.90 0.92 0.94

1.25 1.22 1.19 1.16 1.13

1.34 1.31 1.28 1.25 1.22

0.94 0.91 0.88 0.85 0.82

1.33 1.29 1.26 1.24 1.21

0.96 0.98 1.00 1.02 1.04

1.11 1.08 1.06 1.03 1.01

1.20 1.17 1.15 1.12 1.10

0.80 0.77 0.75 0.72 0.70

1.18 1.16 1.13 1.11 1.08

1.06 1.08 1.10 1.12 1.14

0.99 0.97 0.95 0.93 0.91

1.08 1.06 1.04 1.02 1.00

0.68 0.66 0.64 0.62 0.60

1.06 1.04 1.02 1.00 0.98

1.16 1.18 1.20 1.25 1.30

0.89 0.87 0.86 0.82 0.78

0.98 0.96 0.95 0.91 0.87

0.58 0.56 0.55 0.51 0.47

0.96 0.95 0.93 0.89 0.85

* See Table 5.15, Specific Gravity of Air at Various Temperatures.

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TABLE 2.14 Conversion of Weighings in Air to Weighings in Vacuo (Continued) Buoyancy reduction factor, k Density of object weighed

Brass weights, density ⫽ 8.4

Pt or Pt-Ir weights, density ⫽ 21.5

Al or quartz weights, density ⫽ 2.7

Gold weights, density ⫽ 17

1.35 1.40 1.50 1.6 1.7

0.75 0.71 0.66 0.61 0.56

0.83 0.80 0.74 0.69 0.65

0.44 0.40 0.35 0.30 0.25

0.82 0.79 0.73 0.68 0.64

1.8 1.9 2.0 2.2 2.4

0.52 0.49 0.46 0.40 0.36

0.61 0.58 0.54 0.49 0.44

0.21 0.18 0.15 0.09 0.05

0.60 0.56 0.53 0.48 0.43

2.6 2.8 3.0 3.5 4

0.32 0.29 0.26 0.20 0.16

0.41 0.37 0.34 0.29 0.24

0.01 ⫺0.02 ⫺0.05 ⫺0.11 ⫺0.15

0.39 0.36 0.33 0.27 0.23

5 6 7 8 9

0.10 0.06 0.03 0.01 ⫺0.01

0.18 0.14 0.12 0.09 0.08

⫺0.21 ⫺0.25 ⫺0.28 ⫺0.30 ⫺0.32

0.17 0.13 0.10 0.08 0.06

10 12 14 16 18

⫺0.02 ⫺0.04 ⫺0.06 ⫺0.07 ⫺0.08

0.06 0.04 0.03 0.02 0.01

⫺0.33 ⫺0.35 ⫺0.37 ⫺0.38 ⫺0.39

0.05 0.03 0.02 0.00 0.00

20 22

⫺0.08 ⫺0.09

0.00 0.00

⫺0.39 ⫺0.40

⫺0.01 ⫺0.02

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TABLE 2.15 Hydrometer Conversion Table This table gives the relation between density (c.g.s.) and degrees on the Baume´ and Twaddell scales. The Twaddell scale is never used for densities less than unity. See also Sec. 2.1.2.1, Hydrometers.

Density

Degrees Baume´ (NIST* scale)

Degrees Baume´ (A.P.I.† scale)

Density

Degrees Baume´ (NIST* scale)

Degrees Baume´ (A.P.I.† scale)

0.600 0.605 0.610 0.615 0.620

103.33 101.40 99.51 97.64 95.81

104.33 102.38 100.47 98.58 96.73

0.825 0.830 0.835 0.840 0.845

39.70 38.68 37.66 36.67 35.68

40.02 38.98 37.96 36.95 35.96

0.625 0.630 0.635 0.640 0.645

94.00 92.22 90.47 88.75 87.05

94.90 93.10 91.33 89.59 87.88

0.850 0.855 0.860 0.865 0.870

34.71 33.74 32.79 31.85 30.92

34.97 34.00 33.03 32.08 31.14

0.650 0.655 0.660 0.665 0.670

85.38 83.74 82.12 80.52 78.95

86.19 84.53 82.89 81.28 79.69

0.875 0.880 0.885 0.890

30.00 29.09 28.19 27.30

30.21 29.30 28.39 27.49

0.675 0.680 0.685 0.690 0.695

77.41 75.88 74.38 72.90 71.43

78.13 76.59 75.07 73.57 72.10

0.895 0.900 0.905 0.910 0.915

26.42 25.56 24.70 23.85 23.01

26.60 25.72 24.85 23.99 23.14

0.700 0.705 0.710 0.715 0.720

70.00 68.57 67.18 65.80 64.44

70.64 69.21 67.80 66.40 65.03

0.920 0.925 0.930 0.935 0.940

22.17 21.35 20.54 19.73 18.94

22.30 21.47 20.65 19.84 19.03

0.725 0.730 0.735 0.740 0.745

63.10 61.78 60.48 59.19 57.92

63.67 62.34 61.02 59.72 58.43

0.945 0.950 0.955 0.960 0.965

18.15 17.37 16.60 15.83 15.08

18.24 17.45 16.67 15.90 15.13

0.750 0.755 0.760 0.765 0.770

56.67 55.43 54.21 53.01 51.82

57.17 55.92 54.68 53.47 52.27

0.970 0.975 0.980 0.985 0.990

14.33 13.59 12.86 12.13 11.41

14.38 13.63 12.89 12.15 11.43

0.775 0.780 0.785 0.790 0.795

50.65 49.49 48.34 47.22 46.10

51.08 49.91 48.75 47.61 46.49

0.995 1.000

10.70 10.00

10.71 10.00

0.800 0.805 0.810 0.815 0.820

45.00 43.91 42.84 41.78 40.73

45.38 44.28 43.19 42.12 41.06

DENSITIES GREATER THAN UNITY

Density 1.00 1.01 1.02

Degrees Baume´ (NIST* scale)

Degrees Twaddell

0.00 1.44 2.84

* NIST, National Institute for Science and Technology (formerly the National Bureau of Standards, U.S.). † A.P.I. is the American Petroleum Institute.

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TABLE 2.15 Hydrometer Conversion Table (Continued)

Density

Degrees Baume´ (NIST* scale)

Degrees Twaddell

Density

Degrees Baume´ (NIST* scale)

Degrees Twaddell

1.03 1.04 1.05 1.06 1.07

4.22 5.58 6.91 8.21 9.49

6 8 10 12 14

1.52 1.53 1.54 1.55 1.56

49.60 50.23 50.84 51.45 52.05

104 106 108 110 112

1.08 1.09 1.10 1.11 1.12

10.78 11.97 13.18 14.37 15.54

16 18 20 22 24

1.57 1.58 1.59 1.60 1.61

52.64 53.23 53.80 54.38 54.94

114 116 118 120 122

1.13 1.14 1.15 1.16 1.17

16.68 17.81 18.91 20.00 21.07

26 28 30 32 34

1.62 1.63 1.64 1.65 1.66

55.49 56.04 56.58 57.12 57.65

124 126 128 130 132

1.18 1.19 1.20 1.21 1.22

22.12 23.15 24.17 25.16 26.15

36 38 40 42 44

1.67 1.68 1.69 1.70 1.71

58.17 58.69 59.20 59.71 60.20

134 136 138 140 142

1.23 1.24 1.25 1.26 1.27

27.11 28.06 29.00 29.92 30.83

46 48 50 52 54

1.72 1.73 1.74 1.75 1.76

60.70 61.18 61.67 62.14 62.61

144 146 148 150 152

1.28 1.29 1.30 1.31 1.32

31.72 32.60 33.46 34.31 35.15

56 58 60 62 64

1.77 1.78 1.79 1.80 1.81

63.08 63.54 63.99 64.44 64.89

154 156 158 160 162

1.33 1.34 1.35 1.36 1.37

35.98 36.79 37.59 38.38 39.16

66 68 70 72 74

1.82 1.83 1.84 1.85 1.86

65.31 65.77 66.20 66.62 67.04

164 166 168 170 172

1.38 1.39 1.40 1.41 1.42

39.93 40.68 41.43 42.16 42.89

76 78 80 82 84

1.87 1.88 1.89 1.90 1.91

67.46 67.87 68.28 68.68 69.08

174 176 178 180 182

1.43 1.44 1.45 1.46 1.47

43.60 44.31 45.00 45.68 46.36

86 88 90 92 94

1.92 1.93 1.94 1.95 1.96

69.48 69.87 70.26 70.64 71.02

184 186 188 190 192

1.48 1.49 1.50 1.51

47.03 47.68 48.33 48.97

96 98 100 102

1.97 1.98 1.99 2.00

71.40 71.77 72.14 72.50

194 196 198 200

* NIST, National Institute for Science and Technology (formerly the National Bureau of Standards, U.S.).

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TABLE 2.16 Pressure Conversion Chart

psi 0.01 0.02 0.03 0.04 0.05 0.06 0.07 0.08 0.09 0.10 0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00 2.00 3.00 4.00 5.00 6.00 7.00 8.00 9.00 10.0 14.7 15.0 20.0 25.0 30.0 40.0 50.0 60.0 70.0 80.0 90.0 100.0 150.0 200.0 250.0 300.0 400.0 500.0

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Inches H2O at 4⬚C

Inches Hg at 0⬚C

mmH2O at 4⬚C

mmHg at 0⬚C

0.2768 0.5536 0.8304 1.107 1.384 1.661 1.938 2.214 2.491 2.768 5.536 8.304 11.07 13.84 16.61 19.38 22.14 24.91 27.68 55.36 83.04 110.7 138.4 166.1 193.8 221.4 249.1 276.8 406.9 415.2 553.6 692.0 830.4 1 107 1 384 1 661 1 938 2 214 2 491 2 768 4 152 5 536 6 920 8 304

0.0204 0.0407 0.0611 0.0814 0.1018 0.1222 0.1425 0.1629 0.1832 0.2036 0.4072 0.6108 0.8144 1.018 1.222 1.425 1.629 1.832 2.036 4.072 6.108 8.144 10.18 12.22 14.25 16.29 18.32 20.36 29.93 30.54 40.72 50.90 61.08 81.44 101.8 122.2 142.5 162.9 183.2 203.6 305.4 407.2 509.0 610.8

7.031 14.06 21.09 28.12 35.15 42.18 49.22 56.25 63.28 70.31 140.6 210.9 281.2 351.5 421.8 492.2 562.5 632.8 703.1 1 072 2 109 2 812 3 515 4 218 4 922 5 625 6 328 7 031 10 332 10 550 14 060 17 580 21 090 28 120 35 150 42 180 49 220 56 250 63 280 70 307

0.517 1.034 1.551 2.068 2.586 3.103 3.620 4.137 4.654 5.171 10.34 15.51 20.68 25.86 31.03 36.20 41.37 46.54 51.71 103.4 155.1 206.8 258.6 310.3 362.0 413.7 465.4 517.1 760.0 775.7 1 034 1 293 1 551 2 068 2 586 3 103 3 620 4 137 4 654 5 171 7 757 10 343

atm

Pascals (N · m⫺2)

0.0007 0.0014 0.0020 0.0027 0.0034 0.0041 0.0048 0.0054 0.0061 0.0068 0.0136 0.0204 0.0272 0.0340 0.0408 0.0476 0.0544 0.0612 0.0689 0.1361 0.2041 0.2722 0.3402 0.4083 0.4763 0.5444 0.6124 0.6805 1.000 1.021 1.361 1.701 2.041 2.722 3.402 4.083 4.763 5.444 6.124 6.805 10.21 13.61 17.01 20.41 27.22 34.02

68.95 137.90 206.8 275.8 344.7 413.7 482.6 551.6 620.5 689.5 1 379.9 2 068.5 2 758 3 447 4 137 4 826 5 516 6 205 6 895 13 790 20 684 27 579 34 474 41 369 48 263 55 158 62 053 68 948 101 325 103 421 137 895 172 369 206 843 275 790 344 738 413 685 482 633 551 581 620 528 689 476 1 034 214 1 378 951 1 723 689 2 068 427 2 757 903 3 447 379

1 bar ⫽ 105 pascal.

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(McGHP)

2.88

INTERACTIVE

top of rh base of rh

SECTION 2

TABLE 2.17 Corrections to Be Added to Molar Values to Convert to Molal

cap height base of text

Aqueous solution Temperature, ⬚C

⌬G⬚ J · mol⫺1

⌬H⬚ J · mol⫺1

⌬S⬚ J · deg⫺1 · mol⫺1

⌬C ⬚p J · deg⫺1 · mol⫺1

0 10 20 30 40 50 60

0.4 0.8 4.2 10.9 20.1 32.2 46.8

⫺42.7 58.1 148.1 230.5 313.4 397.9 482.4

⫺0.17 0.21 0.50 0.79 1.09 1.34 1.59

55.2 45.6 38.9 35.1 33.0 32.6 32.2

TABLE 2.18 Molar Equivalent of One Liter of Gas at Various Temperatures and Pressures The values in this table, which give the number of moles in 1 liter of gas, are based on the properties of an “ideal” gas and were calculated by use of the formula: Moles/liter ⫽

P 273 1 ⫻ ⫻ 760 T 22.40

where P is the pressure in millimeters of mercury and T is the temperature in kelvins (⫽t⬚C ⫹ 273). To convert to moles per cubic foot multiply the values in the table by 28.316. Temperature ⬚C

Pressure mm of mercury

10⬚

12⬚

14⬚

16⬚

18⬚

20⬚

655 660 665 670 675

0.03712 3731 3768 3796 3825

0.03686 3714 3742 3770 3798

0.03660 3688 3716 3744 3772

0.03634 3662 3690 3718 3745

0.03610 3637 3665 3692 3720

0.03585 3612 3640 3667 3695

680 685 690 695 700

0.03853 3881 3910 3938 3967

0.03826 3854 3882 3910 3939

0.03800 3827 3855 3883 3911

0.03773 3801 3829 3856 3884

0.03747 3775 3802 3830 3858

0.03694 3749 3776 3804 3831

702 704 706 708 710

0.03978 3989 4000 4012 4023

0.03950 3961 3972 3984 3995

0.03922 3934 3945 3956 3967

0.03895 3906 3917 3929 3940

0.03869 3880 3891 3902 3913

0.03842 3853 3864 3875 3886

712 714 716 718 720

0.04035 4046 4057 4068 4080

0.04006 4018 4029 4040 4051

0.03978 3989 4001 4012 4023

0.03951 3962 3973 3984 3995

0.03924 3935 3946 3957 3968

0.03897 3908 3919 3930 3941

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

2.89

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

TABLE 2.18 Molar Equivalent of One Liter of Gas at Various Temperatures and Pressures (Continued)

top of rh base of rh cap height base of text

Temperature ⬚C

Pressure mm of mercury

10⬚

12⬚

14⬚

16⬚

18⬚

20⬚

722 724 726 728 730

0.04091 4103 4114 4125 4136

0.04063 4074 4085 4096 4108

0.04034 4045 4057 4068 4079

0.04006 4017 4028 4040 4051

0.03979 3990 4001 4012 4023

0.03952 3963 3973 3984 3995

732 734 736 738 740

0.04148 4159 4171 4182 4193

0.04119 4130 4141 4153 4164

0.04090 4101 4112 4124 4135

0.04062 4073 4084 4095 4106

0.04034 4045 4056 4067 4078

0.04006 4017 4028 4039 4050

742 744 746 748 750

0.04204 4216 4227 4239 4250

0.04175 4186 4198 4209 4220

0.04146 4157 4168 4179 4191

0.04117 4128 4139 4151 4162

0.04089 4100 4111 4122 4133

0.04061 4072 4038 4094 4105

752 754 756 758 760

0.04261 4273 4284 4295 4307

0.04231 4243 4254 4265 4276

0.04202 4213 4224 4235 4247

0.04173 4184 4195 4206 4217

0.04144 4155 4166 4177 4188

0.04116 4127 4138 4149 4160

762 764 766 768 770

0.04318 4329 4341 4352 4363

0.04287 4299 4310 4321 4333

0.04258 4269 4280 4291 4302

0.04228 4239 4250 4262 4273

0.04199 4210 4221 4232 4243

0.04171 4181 4192 4203 4214

772 774 776 778 780

0.04375 4386 4397 4409 4420

0.04344 4355 4366 4378 4389

0.04314 4325 4336 4347 4358

0.04284 4295 4306 4317 4328

0.04254 4265 4276 4287 4298

0.04225 4236 4247 4258 4269

Temperature ⬚C

Pressure mm of mercury

22⬚

24⬚

26⬚

28⬚

30⬚

32⬚

655 660 665 670 675

0.03561 3588 3614 3642 3669

0.03537 3564 3591 3618 3645

0.03515 3541 3568 3595 3622

0.03490 3516 3543 3569 3596

0.03467 3493 3520 3546 3572

0.03444 3470 3496 3523 3549

680 685 690 695 700

0.03697 3724 3751 3778 3805

0.03672 3699 3726 3753 3780

0.03649 3676 3702 3729 3756

0.03623 3649 3676 3703 3729

0.03599 3625 3652 3678 3705

0.03575 3602 3628 3654 3680

short standard long

DEAN #37261

LEFT

(McGHP)

2.90

INTERACTIVE

top of rh base of rh

SECTION 2

TABLE 2.18 Molar Equivalent of One Liter of Gas at Various Temperatures and Pressures (Continued)

cap height base of text

Temperature ⬚C

Pressure mm of mercury

22⬚

24⬚

26⬚

28⬚

30⬚

32⬚

702 704 706 708 710

0.03816 3827 3838 3849 3860

0.03790 3801 3812 3823 3834

0.03767 3777 3788 3799 3810

0.03740 3750 3761 3772 3783

0.03715 3726 3736 3747 3758

0.03691 3701 3712 3722 3733

712 714 716 718 720

0.03870 3881 3892 3902 3914

0.03844 3855 3866 3877 3888

0.03820 3831 3842 3853 3863

0.03793 3804 3815 3825 3836

0.03768 3779 3789 3800 3811

0.03744 3754 3765 3775 3786

722 724 726 728 730

0.03925 3936 3947 3957 3968

0.03898 3909 3920 3931 3941

0.03874 3885 3896 3906 3917

0.03847 3857 3868 3878 3889

0.03821 3832 3842 3853 3863

0.03796 3807 3817 3828 3838

732 734 736 738 740

0.03979 3990 4001 4012 4023

0.03952 3963 3974 3985 3995

0.03928 3938 3949 3960 3971

0.03900 3910 3921 3932 3942

0.03874 3885 3895 3906 3916

0.03849 3859 3870 3880 3891

742 744 746 748 750

0.04033 4044 4055 4066 4077

0.04006 4017 4028 4039 4049

0.03981 3992 4003 4014 4024

0.03953 3964 3974 3985 3996

0.03927 3938 3948 3959 3969

0.03901 3912 3922 3933 3943

752 754 756 758 760

0.04088 4099 4110 4121 4131

0.04060 4071 4082 4093 4103

0.04035 4046 4056 4067 4078

0.04006 4017 4028 4038 4049

0.03980 3991 4001 4012 4022

0.03954 3964 3975 3985 3996

762 764 766 768 770

0.04142 4153 4164 4175 4186

4114 4125 4136 4147 4158

4089 4099 4110 4121 4132

4060 4070 4081 4092 4102

4033 4043 4054 4065 4075

4006 4017 4027 4038 4048

772 774 776 778 780

0.04197 4207 4218 4229 4240

0.04168 4179 4190 4201 4211

0.04142 4153 4164 4175 4185

0.04113 4124 4134 4145 4155

0.04086 4096 4107 4117 4128

0.04059 4070 4080 4091 4101

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

2.91

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

TABLE 2.19 Factors for Reducing Gas Volumes to Normal (Standard) Temperature and Pressure (760 mmHg)

top of rh base of rh cap height base of text

Examples: (a) 20 mL of dry gas at 22⬚C and 730 mm ⫽ 20 ⫻ 0.8888 ⫽ 17.78 mL at 0⬚C and 760 mm. (b) 20 mL of a gas over water at 22⬚ and 730 mm ⫽ 20 ⫻ (factor corrected for aqueous tension; i.e., 730 ⫺ 19.8 or 710.2 mm) ⫽ 20 mL of dry gas at 22⬚ and 710.2 mm ⫽ 20 ⫻ 0.86475 ⫽ 17.30 mL at 0⬚C and 760 mm. Mass in milligrams of 1 mL of gas at S.T.P.: acetylene, 1.173; carbon dioxide, 1.9769; hydrogen, 0.0899; nitric oxide (NO), 1.3402; nitrogen, 1.25057; oxygen, 1.42904. Temperature ⬚C

Pressure mm of mercury

10⬚

11⬚

12⬚

13⬚

14⬚

15⬚

16⬚

17⬚

670 672 674 676 678

0.8504 0.8530 0.8555 0.8580 0.8606

0.8474 0.8500 0.8525 0.8550 0.8576

0.8445 0.8470 0.8495 0.8520 0.8545

0.8415 0.8440 0.8465 0.8490 0.8516

0.8386 0.8411 0.8436 0.8461 0.8486

0.8357 0.8382 0.8407 0.8431 0.8456

0.8328 0.8353 0.8377 0.8402 0.8427

0.8299 0.8324 0.8349 0.8373 0.8398

680 682 684 686 688

0.8631 0.8657 0.8682 0.8707 0.8733

0.8601 0.8626 0.8651 0.8677 0.8702

0.8571 0.8596 0.8621 0.8646 0.8672

0.8541 0.8566 0.8591 0.8616 0.8641

0.8511 0.8536 0.8561 0.8586 0.8611

0.8481 0.8506 0.8531 0.8556 0.8581

0.8452 0.8477 0.8502 0.8527 0.8551

0.8423 0.8448 0.8472 0.8497 0.8522

690 692 694 696 698

0.8758 0.8784 0.8809 0.8834 0.8860

0.8727 0.8753 0.8778 0.8803 0.8828

0.8697 0.8722 0.8747 0.8772 0.8798

0.8666 0.8691 0.8717 0.8742 0.8767

0.8636 0.8661 0.8686 0.8711 0.8736

0.8606 0.8631 0.8656 0.8681 0.8706

0.8576 0.8601 0.8626 0.8651 0.8676

0.8547 0.8572 0.8596 0.8621 0.8646

700 702 704 706 708

0.8885 0.8910 0.8936 0.8961 0.8987

0.8854 0.8879 0.8904 0.8930 0.8955

0.8823 0.8848 0.8873 0.8898 0.8924

0.8792 0.8817 0.8842 0.8867 0.8892

0.8761 0.8786 0.8811 0.8836 0.8861

0.8731 0.8756 0.8781 0.8806 0.8831

0.8700 0.8725 0.8750 0.8775 0.8800

0.8671 0.8695 0.8720 0.8745 0.8770

710 712 714 716 718

0.9012 0.9037 0.9063 0.9088 0.9114

0.8980 0.9006 0.9031 0.9056 0.9081

0.8949 0.8974 0.8999 0.9024 0.9050

0.8917 0.8943 0.8968 0.8993 0.9018

0.8886 0.8911 0.8936 0.8961 0.8987

0.8856 0.8880 0.8905 0.8930 0.8955

0.8825 0.8850 0.8875 0.8899 0.8924

0.8794 0.8819 0.8844 0.8869 0.8894

720 722 724 726 728

0.9139 0.9164 0.9190 0.9215 0.9241

0.9107 0.9132 0.9157 0.9183 0.9208

0.9075 0.9100 0.9125 0.9151 0.9176

0.9043 0.9068 0.9093 0.9118 0.9144

0.9012 0.9037 0.9062 0.9087 0.9112

0.8980 0.9005 0.9030 0.9055 0.9080

0.8949 0.8974 0.8999 0.9024 0.9049

0.8918 0.8943 0.8968 0.8993 0.9017

730 732 734 736 738

0.9266 0.9291 0.9317 0.9342 0.9368

0.9233 0.9259 0.9284 0.9309 0.9334

0.9201 0.9226 0.9251 0.9277 0.9302

0.9169 0.9194 0.9219 0.9244 0.9269

0.9137 0.9162 0.9187 0.9212 0.9237

0.9105 0.9130 0.9155 0.9180 0.9205

0.9073 0.9098 0.9123 0.9148 0.9173

0.9042 0.9067 0.9092 0.9117 0.9141

740 742 744 746 748

0.9393 0.9418 0.9444 0.9469 0.9494

0.9360 0.9385 0.9410 0.9436 0.9461

0.9327 0.9352 0.9377 0.9403 0.9428

0.9294 0.9319 0.9345 0.9370 0.9395

0.9262 0.9287 0.9312 0.9337 0.9362

0.9230 0.9255 0.9280 0.9305 0.9329

0.9198 0.9223 0.9248 0.9272 0.9297

0.9166 0.9191 0.9216 0.9240 0.9265

short standard long

DEAN #37261

LEFT

(McGHP)

2.92

INTERACTIVE

top of rh base of rh

SECTION 2

cap height base of text

TABLE 2.19 Factors for Reducing Gas Volumes to Normal (Standard) Temperature and Pressure (Continued) Temperature ⬚C

Pressure mm of mercury

10⬚

11⬚

12⬚

13⬚

14⬚

15⬚

16⬚

17⬚

750 752 754 756 758

0.9520 0.9545 0.9571 0.9596 0.9621

0.9486 0.9511 0.9537 0.9562 0.9587

0.9453 0.9478 0.9504 0.9529 0.9554

0.9420 0.9445 0.9470 0.9495 0.9520

0.9387 0.9412 0.9437 0.9462 0.9487

0.9354 0.9379 0.9404 0.9429 0.9454

0.9322 0.9347 0.9372 0.9397 0.9422

0.9290 0.9315 0.9339 0.9364 0.9389

760 762 764 766 768

0.9647 0.9672 0.9698 0.9723 0.9748

0.9613 0.9638 0.9663 0.9689 0.9714

0.9579 0.9604 0.9630 0.9655 0.9680

0.9546 0.9571 0.9596 0.9620 0.9646

0.9512 0.9537 0.9562 0.9587 0.9612

0.9479 0.9504 0.9529 0.9554 0.9579

0.9446 0.9471 0.9496 0.9521 0.9546

0.9414 0.9439 0.9463 0.9488 0.9513

770 772 774 776 778

0.9774 0.9799 0.9825 0.9850 0.9875

0.9739 0.9764 0.9790 0.9815 0.9840

0.9705 0.9730 0.9756 0.9781 0.9806

0.9671 0.9696 0.9721 0.9746 0.9772

0.9637 0.9662 0.9687 0.9712 0.9737

0.9604 0.9629 0.9654 0.9679 0.9704

0.9571 0.9596 0.9620 0.9645 0.9670

0.9538 0.9562 0.9587 0.9612 0.9637

780 782 784 786 788

0.9901 0.9926 0.9952 0.9977 1.0002

0.9866 0.9891 0.9916 0.9942 0.9967

0.9831 0.9856 0.9882 0.9907 0.9932

0.9797 0.9822 0.9847 0.9872 0.9897

0.9763 0.9788 0.9813 0.9838 0.9863

0.9729 0.9754 0.9778 0.9803 0.9828

0.9695 0.9720 0.9745 0.9770 0.9794

0.9662 0.9686 0.9711 0.9736 0.9761

Temperature ⬚C

Pressure mm of mercury

18⬚

19⬚

20⬚

21⬚

22⬚

23⬚

24⬚

25⬚

670 672 674 676 678

0.8270 0.8295 0.8320 0.8345 0.8369

0.8242 0.8267 0.8291 0.8316 0.8341

0.8214 0.8239 0.8263 0.8288 0.8312

0.8186 0.8211 0.8235 0.8259 0.8284

0.8158 0.8183 0.8207 0.8231 0.8256

0.8131 0.8155 0.8179 0.8204 0.8228

0.8103 0.8128 0.8152 0.8176 0.8200

0.8076 0.8100 0.8124 0.8149 0.8173

680 682 684 686 688

0.8394 0.8419 0.8443 0.8468 0.8493

0.8365 0.8390 0.8414 0.8439 0.8464

0.8337 0.8361 0.8386 0.8410 0.8435

0.8308 0.8333 0.8357 0.8382 0.8406

0.8280 0.8304 0.8329 0.8353 0.8378

0.8252 0.8276 0.8301 0.8325 0.8349

0.8224 0.8249 0.8273 0.8297 0.8321

0.8197 0.8221 0.8245 0.8269 0.8293

690 692 694 696 698

0.8517 0.8542 0.8567 0.8591 0.8616

0.8488 0.8513 0.8537 0.8562 0.8587

0.8459 0.8484 0.8508 0.8533 0.8557

0.8430 0.8455 0.8479 0.8504 0.8528

0.8402 0.8426 0.8451 0.8475 0.8499

0.8373 0.8398 0.8422 0.8446 0.8471

0.8345 0.8369 0.8394 0.8418 0.8442

0.8317 0.8341 0.8366 0.8390 0.8414

700 702 704 706 708

0.8641 0.8665 0.8690 0.8715 0.8740

0.8611 0.8636 0.8660 0.8685 0.8710

0.8582 0.8606 0.8631 0.8655 0.8680

0.8553 0.8577 0.8602 0.8626 0.8650

0.8524 0.8547 0.8572 0.8597 0.8621

0.8495 0.8519 0.8543 0.8568 0.8592

0.8466 0.8490 0.8515 0.8539 0.8563

0.8438 0.8462 0.8486 0.8510 0.8534

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

2.93

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

top of rh base of rh cap height base of text

TABLE 2.19 Factors for Reducing Gas Volumes to Normal (Standard) Temperature and Pressure (Continued) Temperature ⬚C

Pressure mm of mercury

18⬚

19⬚

20⬚

21⬚

22⬚

23⬚

24⬚

25⬚

710 712 714 716 718

0.8764 0.8789 0.8814 0.8838 0.8863

0.8734 0.8759 0.8783 0.8808 0.8833

0.8704 0.8729 0.8753 0.8778 0.8802

0.8675 0.8699 0.8724 0.8748 0.8773

0.8645 0.8670 0.8694 0.8718 0.8743

0.8616 0.8640 0.8665 0.8689 0.8713

0.8587 0.8611 0.8636 0.8660 0.8684

0.8558 0.8582 0.8607 0.8631 0.8655

720 722 724 726 728

0.8888 0.8912 0.8937 0.8962 0.8986

0.8857 0.8882 0.8906 0.8931 0.8956

0.8827 0.8852 0.8876 0.8901 0.8925

0.8797 0.8821 0.8846 0.8870 0.8895

0.8767 0.8792 0.8816 0.8840 0.8865

0.8738 0.8762 0.8786 0.8810 0.8835

0.8708 0.8732 0.8757 0.8781 0.8805

0.8679 0.8703 0.8727 0.8751 0.8775

730 732 734 736 738

0.9011 0.9036 0.9060 0.9085 0.9110

0.8980 0.9005 0.9029 0.9054 0.9079

0.8950 0.8974 0.8999 0.9023 0.9048

0.8919 0.8944 0.8968 0.8992 0.9017

0.8889 0.8913 0.8938 0.8962 0.8986

0.8859 0.8883 0.8907 0.8932 0.8956

0.8829 0.8853 0.8877 0.8902 0.8926

0.8799 0.8824 0.8848 0.8872 0.8896

740 742 744 746 748

0.9135 0.9159 0.9184 0.9209 0.9233

0.9103 0.9128 0.9153 0.9177 0.9202

0.9072 0.9097 0.9121 0.9146 0.9170

0.9041 0.9066 0.9090 0.9115 0.9139

0.9011 0.9035 0.9059 0.9084 0.9108

0.8980 0.9005 0.9029 0.9053 0.9077

0.8950 0.8974 0.8998 0.9023 0.9047

0.8920 0.8944 0.8968 0.8992 0.9016

750 752 754 756 758

0.9258 0.9283 0.9307 0.9332 0.9357

0.9226 0.9251 0.9276 0.9300 0.9325

0.9195 0.9219 0.9244 0.9268 0.9293

0.9164 0.9188 0.9212 0.9237 0.9261

0.9132 0.9157 0.9181 0.9206 0.9230

0.9102 0.9126 0.9150 0.9174 0.9199

0.9071 0.9095 0.9119 0.9144 0.9168

0.9041 0.9065 0.9089 0.9113 0.9137

760 762 764 766 768

0.9381 0.9406 0.9431 0.9456 0.9480

0.9349 0.9374 0.9399 0.9423 0.9448

0.9317 0.9342 0.9366 0.9391 0.9415

0.9286 0.9310 0.9335 0.9359 0.9383

0.9254 0.9279 0.9303 0.9327 0.9352

0.9223 0.9247 0.9272 0.9296 0.9320

0.9192 0.9216 0.9240 0.9265 0.9289

0.9161 0.9185 0.9209 0.9233 0.9258

770 772 774 776 778

0.9505 0.9530 0.9554 0.9579 0.9604

0.9472 0.9497 0.9522 0.9546 0.9571

0.9440 0.9464 0.9489 0.9514 0.9538

0.9408 0.9432 0.9457 0.9481 0.9506

0.9376 0.9400 0.9425 0.9449 0.9473

0.9344 0.9369 0.9393 0.9417 0.9441

0.9313 0.9337 0.9361 0.9385 0.9410

0.9282 0.9306 0.9330 0.9354 0.9378

780 782 784 786 788

0.9628 0.9653 0.9678 0.9702 0.9727

0.9595 0.9620 0.9645 0.9669 0.9694

0.9563 0.9587 0.9612 0.9636 0.9661

0.9530 0.9555 0.9579 0.9603 0.9628

0.9498 0.9522 0.9546 0.9571 0.9595

0.9466 0.9490 0.9514 0.9538 0.9563

0.9434 0.9458 0.9482 0.9506 0.9531

0.9402 0.9426 0.9450 0.9474 0.9499

short standard long

DEAN #37261

LEFT

(McGHP)

2.94

INTERACTIVE

top of rh base of rh

SECTION 2

cap height base of text

TABLE 2.19 Factors for Reducing Gas Volumes to Normal (Standard) Temperature and Pressure (Continued) Temperature ⬚C

Pressure mm of mercury

26⬚

27⬚

28⬚

29⬚

30⬚

31⬚

32⬚

33⬚

670 672 674 676 678

0.8049 0.8073 0.8097 0.8121 0.8145

0.8022 0.8046 0.8070 0.8094 0.8118

0.7996 0.8020 0.8043 0.8067 0.8091

0.7969 0.7993 0.8017 0.8041 0.8064

0.7943 0.7967 0.7990 0.8014 0.8038

0.7917 0.7940 0.7964 0.7988 0.8011

0.7891 0.7914 0.7938 0.7962 0.7985

0.7865 0.7889 0.7912 0.7936 0.7959

680 682 684 686 688

0.8169 0.8193 0.8217 0.8241 0.8265

0.8142 0.8166 0.8190 0.8214 0.8238

0.8115 0.8139 0.8163 0.8187 0.8211

0.8088 0.8112 0.8136 0.8160 0.8183

0.8061 0.8085 0.8109 0.8133 0.8156

0.8035 0.8059 0.8082 0.8106 0.8129

0.8009 0.8032 0.8056 0.8079 0.8103

0.7982 0.8006 0.8029 0.8053 0.8076

690 692 694 696 698

0.8289 0.8313 0.8338 0.8362 0.8386

0.8262 0.8286 0.8310 0.8334 0.8358

0.8234 0.8258 0.8282 0.8306 0.8330

0.8207 0.8231 0.8255 0.8278 0.8302

0.8180 0.8204 0.8227 0.8251 0.8275

0.8153 0.8177 0.8200 0.8224 0.8248

0.8126 0.8150 0.8174 0.8197 0.8221

0.8100 0.8123 0.8147 0.8170 0.8194

700 702 704 706 708

0.8410 0.8434 0.8458 0.8482 0.8506

0.8382 0.8406 0.8429 0.8453 0.8477

0.8354 0.8378 0.8401 0.8425 0.8449

0.8326 0.8350 0.8374 0.8397 0.8421

0.8299 0.8322 0.8346 0.8370 0.8393

0.8271 0.8295 0.8319 0.8342 0.8366

0.8244 0.8268 0.8291 0.8315 0.8338

0.8217 0.8241 0.8264 0.8288 0.8311

710 712 714 716 718

0.8530 0.8554 0.8578 0.8602 0.8626

0.8501 0.8525 0.8549 0.8573 0.8597

0.8473 0.8497 0.8521 0.8545 0.8569

0.8445 0.8469 0.8493 0.8516 0.8540

0.8417 0.8441 0.8465 0.8488 0.8512

0.8389 0.8413 0.8437 0.8460 0.8484

0.8362 0.8386 0.8409 0.8433 0.8456

0.8335 0.8358 0.8382 0.8405 0.8429

720 722 724 726 728

0.8650 0.8674 0.8698 0.8722 0.8746

0.8621 0.8645 0.8669 0.8693 0.8717

0.8592 0.8616 0.8640 0.8664 0.8688

0.8564 0.8588 0.8612 0.8635 0.8659

0.8536 0.8559 0.8583 0.8607 0.8631

0.8508 0.8531 0.8555 0.8579 0.8602

0.8480 0.8503 0.8527 0.8550 0.8574

0.8452 0.8475 0.8499 0.8522 0.8546

730 732 734 736 738

0.8770 0.8794 0.8818 0.8842 0.8866

0.8741 0.8765 0.8789 0.8813 0.8837

0.8712 0.8736 0.8759 0.8783 0.8807

0.8683 0.8707 0.8730 0.8754 0.8778

0.8654 0.8678 0.8702 0.8725 0.8749

0.8626 0.8649 0.8673 0.8697 0.8720

0.8598 0.8621 0.8645 0.8668 0.8692

0.8569 0.8593 0.8616 0.8640 0.8663

740 742 744 746 748

0.8890 0.8914 0.8938 0.8962 0.8986

0.8861 0.8884 0.8908 0.8932 0.8956

0.8831 0.8855 0.8879 0.8903 0.8927

0.8802 0.8826 0.8849 0.8873 0.8897

0.8773 0.8796 0.8820 0.8844 0.8868

0.8744 0.8768 0.8791 0.8815 0.8838

0.8715 0.8739 0.8762 0.8786 0.8809

0.8687 0.8710 0.8734 0.8757 0.8781

750 752 754 756 758

0.9010 0.9034 0.9058 0.9082 0.9106

0.8980 0.9004 0.9028 0.9052 0.9076

0.8950 0.8974 0.8998 0.9022 0.9046

0.8921 0.8945 0.8968 0.8992 0.9016

0.8891 0.8915 0.8939 0.8962 0.8986

0.8862 0.8886 0.8909 0.8933 0.8957

0.8833 0.8857 0.8880 0.8904 0.8927

0.8804 0.8828 0.8851 0.8875 0.8898

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

2.95

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

top of rh base of rh cap height base of text

TABLE 2.19 Factors for Reducing Gas Volumes to Normal (Standard) Temperature and Pressure (Continued) Temperature ⬚C

Pressure mm of mercury

26⬚

27⬚

28⬚

29⬚

30⬚

31⬚

32⬚

33⬚

760 762 764 766 768

0.9130 0.9154 0.9178 0.9202 0.9227

0.9100 0.9124 0.9148 0.9172 0.9196

0.9070 0.9094 0.9118 0.9141 0.9165

0.9040 0.9064 0.9087 0.9111 0.9135

0.9010 0.9034 0.9057 0.9081 0.9105

0.8980 0.9004 0.9028 0.9051 0.9075

0.8951 0.8974 0.8998 0.9021 0.9045

0.8922 0.8945 0.8969 0.8992 0.9015

770 772 774 776 778

0.9251 0.9275 0.9299 0.9323 0.9347

0.9220 0.9244 0.9268 0.9292 0.9316

0.9189 0.9213 0.9237 0.9261 0.9285

0.9159 0.9182 0.9206 0.9230 0.9254

0.9128 0.9152 0.9176 0.9200 0.9223

0.9098 0.9122 0.9146 0.9169 0.9193

0.9069 0.9092 0.9116 0.9139 0.9163

0.9039 0.9062 0.9086 0.9109 0.9133

780 782 784 786 788

0.9371 0.9395 0.9419 0.9443 0.9467

0.9340 0.9363 0.9387 0.9411 0.9435

0.9308 0.9332 0.9356 0.9380 0.9404

0.9278 0.9301 0.9325 0.9349 0.9373

0.9247 0.9271 0.9294 0.9318 0.9342

0.9217 0.9240 0.9264 0.9287 0.9311

0.9186 0.9210 0.9233 0.9257 0.9281

0.9156 0.9180 0.9203 0.9227 0.9250

Temperature ⬚C

Pressure mm of mercury

34⬚

35⬚

670 672 674 676 678

0.7839 0.7863 0.7886 0.7910 0.7933

680 682 684 686 688

Temperature ⬚C

36⬚

Pressure mm of mercury

34⬚

35⬚

36⬚

0.7814 0.7837 0.7861 0.7884 0.7907

0.7789 0.7812 0.7835 0.7858 0.7882

730 732 734 736 738

0.8541 0.8565 0.8588 0.8612 0.8635

0.8514 0.8537 0.8560 0.8584 0.8607

0.8486 0.8509 0.8533 0.8556 0.8579

0.7956 0.7980 0.8003 0.8027 0.8050

0.7931 0.7954 0.7977 0.8001 0.8024

0.7905 0.7928 0.7951 0.7975 0.7998

740 742 744 746 748

0.8658 0.8682 0.8705 0.8729 0.8752

0.8630 0.8654 0.8677 0.8700 0.8724

0.8602 0.8626 0.8649 0.8672 0.8695

690 692 694 696 698 700 702 704 706 708

0.8073 0.8097 0.8120 0.8144 0.8167 0.8190 0.8214 0.8237 0.8261 0.8284

0.8047 0.8071 0.8094 0.8117 0.8141 0.8164 0.8187 0.8211 0.8234 0.8257

0.8021 0.8044 0.8068 0.8091 0.8114 0.8137 0.8161 0.8184 0.8207 0.8230

750 752 754 756 758 760 762 764 766 768

0.8775 0.8799 0.8822 0.8846 0.8869 0.8892 0.8916 0.8939 0.8963 0.8986

0.8747 0.8770 0.8794 0.8817 0.8840 0.8864 0.8887 0.8910 0.8934 0.8957

0.8719 0.8742 0.8765 0.8788 0.8812 0.8835 0.8858 0.8881 0.8905 0.8928

710 712 714 716 718

0.8307 0.8331 0.8354 0.8378 0.8401

0.8281 0.8304 0.8327 0.8350 0.8374

0.8254 0.8277 0.8300 0.8323 0.8347

770 772 774 776 778

0.9009 0.9033 0.9056 0.9080 0.9103

0.8980 0.9004 0.9027 0.9050 0.9074

0.8951 0.8974 0.8998 0.9021 0.9044

720 722 724 726 728

0.8424 0.8448 0.8471 0.8495 0.8518

0.8397 0.8420 0.8444 0.8467 0.8490

0.8370 0.8393 0.8416 0.8440 0.8463

780 782 784 786 788

0.9127 0.9150 0.9173 0.9197 0.9220

0.9097 0.9120 0.9144 0.9167 0.9190

0.9067 0.9091 0.9114 0.9137 0.9160

short standard long

DEAN #37261

LEFT

(McGHP)

2.96

INTERACTIVE

top of rh base of rh

SECTION 2

cap height base of text

TABLE 2.20 Values of Absorbance for Percent Absorption To convert percent absorption (% A) to absorbance, find the present absorption to the nearest whole digit in the left-hand column; read across to the column located under the tenth of a percent desired, and read the value of absorbance. The value of absorbance corresponding to 26.8% absorption is thus 0.1355. %A

.0

.1

.2

.3

.4

.5

.6

.7

.8

.9

0.0 1.0 2.0 3.0 4.0 5.0

.0000 .0044 .0088 .0132 .0177 .0223

.0004 .0048 .0092 .0137 .0182 .0227

.0009 .0052 .0097 .0141 .0186 .0232

.0013 .0057 .0101 .0146 .0191 .0236

.0017 .0061 .0106 .0150 .0195 .0241

.0022 .0066 .0110 .0155 .0200 .0246

.0026 .0070 .0114 .0159 .0205 .0250

.0031 .0074 .0119 .0164 .0209 .0255

.0035 .0079 .0123 .0168 .0214 .0259

.0039 .0083 .0128 .0173 .0218 .0264

6.0 7.0 8.0 9.0 10.0 11.0

.0269 .0315 .0362 .0410 .0458 .0506

.0273 .0320 .0367 .0414 .0462 .0511

.0278 .0325 .0372 .0419 .0467 .0516

.0283 .0329 .0376 .0424 .0472 .0521

.0287 .0334 .0381 .0429 .0477 .0526

.0292 .0339 .0386 .0434 .0482 .0531

.0297 .0343 .0391 .0438 .0487 .0535

.0301 .0348 .0395 .0443 .0491 .0540

.0306 .0353 .0400 .0448 .0496 .0545

.0311 .0357 .0405 .0453 .0501 .0550

12.0 13.0 14.0 15.0 16.0 17.0

.0555 .0605 .0655 .0706 .0757 .0809

.0560 .0610 .0660 .0711 .0762 .0814

.0565 .0615 .0665 .0716 .0768 .0820

.0570 .0620 .0670 .0721 .0773 .0825

.0575 .0625 .0675 .0726 .0778 .0830

.0580 .0630 .0680 .0731 .0783 .0835

.0585 .0635 .0685 .0737 .0788 .0841

.0590 .0640 .0691 .0742 .0794 .0846

.0595 .0645 .0696 .0747 .0799 .0851

.0600 .0650 .0701 .0752 .0804 .0857

18.0 19.0 20.0 21.0 22.0 23.0

.0862 .0915 .0969 .1024 .1079 .1135

.0867 .0921 .0975 .1029 .1085 .1141

.0872 .0926 .0980 .1035 .1090 .1146

.0878 .0931 .0985 .1040 .1096 .1152

.0883 .0937 .0991 .1046 .1101 .1158

.0888 .0942 .0996 .1051 .1107 .1163

.0894 .0947 .1002 .1057 .1113 .1169

.0899 .0953 .1007 .1062 .1118 .1175

.0904 .0958 .1013 .1068 .1124 .1180

.0910 .0964 .1018 .1073 .1129 .1186

24.0 25.0 26.0 27.0 28.0 29.0

.1192 .1249 .1308 .1367 .1427 .1487

.1198 .1255 .1314 .1373 .1433 .1494

.1203 .1261 .1319 .1379 .1439 .1500

.1209 .1267 .1325 .1385 .1445 .1506

.1215 .1273 .1331 .1391 .1451 .1512

.1221 .1278 .1337 .1397 .1457 .1518

.1226 .1284 .1343 .1403 .1463 .1524

.1232 .1290 .1349 .1409 .1469 .1530

.1238 .1296 .1355 .1415 .1475 .1537

.1244 .1302 .1361 .1421 .1481 .1543

30.0 31.0 32.0 33.0 34.0 35.0

.1549 .1612 .1675 .1739 .1805 .1871

.1555 .1618 .1681 .1746 .1811 .1878

.1561 .1624 .1688 .1752 .1818 .1884

.1568 .1630 .1694 .1759 .1824 .1891

.1574 .1637 .1701 .1765 .1831 .1898

.1580 .1643 .1707 .1772 .1838 .1904

.1586 .1649 .1713 .1778 .1844 .1911

.1593 .1656 .1720 .1785 .1851 .1918

.1599 .1662 .1726 .1791 .1858 .1925

.1605 .1669 .1733 .1798 .1864 .1931

36.0 37.0 38.0 39.0 40.0 41.0

.1938 .2007 .2076 .2147 .2218 .2291

.1945 .2013 .2083 .2154 .2226 .2299

.1952 .2020 .2090 .2161 .2233 .2306

.1959 .2027 .2097 .2168 .2240 .2314

.1965 .2034 .2104 .2175 .2248 .2321

.1972 .2041 .2111 .2182 .2255 .2328

.1979 .2048 .2118 .2190 .2262 .2336

.1986 .2055 .2125 .2197 .2269 .2343

.1993 .2062 .2132 .2204 .2277 .2351

.2000 .2069 .2140 .2211 .2284 .2358

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

2.97

GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

top of rh base of rh cap height base of text

TABLE 2.20 Values of Absorbance for Percent Absorption (Continued) %A

.0

.1

.2

.3

.4

.5

.6

.7

.8

.9

42.0 43.0 44.0 45.0 46.0 47.0

.2366 .2441 .2518 .2596 .2676 .2757

.2373 .2449 .2526 .2604 .2684 .2765

.2381 .2457 .2534 .2612 .2692 .2774

.2388 .2464 .2541 .2620 .2700 .2782

.2396 .2472 .2549 .2628 .2708 .2790

.2403 .2480 .2557 .2636 .2716 .2798

.2411 .2487 .2565 .2644 .2725 .2807

.2418 .2495 .2573 .2652 .2733 .2815

.2426 .2503 .2581 .2660 .2741 .2823

.2434 .2510 .2588 .2668 .2749 .2832

48.0 49.0 50.0 51.0 52.0 53.0

.2840 .2924 .3010 .3098 .3188 .3279

.2848 .2933 .3019 .3107 .3197 .3288

.2857 .2941 .3028 .3116 .3206 .3298

.2865 .2950 .3036 .3125 .3215 .3307

.2874 .2958 .3045 .3134 .3224 .3316

.2882 .2967 .3054 .3143 .3233 .3325

.2890 .2976 .3063 .3152 .3242 .3335

.2899 .2984 .3072 .3161 .3251 .3344

.2907 .2993 .3080 .3170 .3261 .3354

.2916 .3002 .3089 .3179 .3270 .3363

54.0 55.0 56.0 57.0 58.0 59.0

.3372 .3468 .3565 .3665 .3768 .3872

.3382 .3478 .3575 .3675 .3778 .3883

.3391 .3487 .3585 .3686 .3788 .3893

.3401 .3497 .3595 .3696 .3799 .3904

.3410 .3507 .3605 .3706 .3809 .3915

.3420 .3516 .3615 .3716 .3820 .3925

.3429 .3526 .3625 .3726 .3830 .3936

.3439 .3536 .3635 .3737 .3840 .3947

.3449 .3546 .3645 .3747 .3851 .3958

.3458 .3556 .3655 .3757 .3862 .3969

60.0 61.0 62.0 63.0 64.0 65.0

.3979 .4089 .4202 .4318 .4437 .4559

.3990 .4101 .4214 .4330 .4449 .4572

.4001 .4112 .4225 .4342 .4461 .4584

.4012 .4123 .4237 .4353 .4473 .4597

.4023 .4134 .4248 .4365 .4485 .4609

.4034 .4145 .4260 .4377 .4498 .4622

.4045 .4157 .4271 .4389 .4510 .4634

.4056 .4168 .4283 .4401 .4522 .4647

.4067 .4179 .4295 .4413 .4535 .4660

.4078 .4191 .4306 .4425 .4547 .4672

66.0 67.0 68.0 69.0 70.0 71.0

.4685 .4815 .4948 .5086 .5229 .5376

.4698 .4828 .4962 .5100 .5243 .5391

.4711 .4841 .4976 .5114 .5258 .5406

.4724 .4855 .4989 .5129 .5272 .5421

.4737 .4868 .5003 .5143 .5287 .5436

.4750 .4881 .5017 .5157 .5302 .5452

.4763 .4895 .5031 .5171 .5317 .5467

.4776 .4908 .5045 .5186 .5331 .5482

.4789 .4921 .5058 .5200 .5346 .5498

.4802 .4935 .5072 .5214 .5361 .5513

72.0 73.0 74.0 75.0 76.0 77.0

.5528 .5686 .5850 .6021 .6198 .6383

.5544 .5702 .5867 .6038 .6216 .6402

.5560 .5719 .5884 .6055 .6234 .6421

.5575 .5735 .5901 .6073 .6253 .6440

.5591 .5751 .5918 .6091 .6271 .6459

.5607 .5768 .5935 .6108 .6289 .6478

.5622 .5784 .5952 .6126 .6308 .6498

.5638 .5800 .5969 .6144 .6326 .6517

.5654 .5817 .5986 .6162 .6345 .6536

.5670 .5834 .6003 .6180 .6364 .6556

78.0 79.0 80.0 81.0 82.0 83.0

.6576 .6778 .6990 .7212 .7447 .7696

.6596 .6799 .7011 .7235 .7471 .7721

.6615 .6819 .7033 .7258 .7496 .7747

.6635 .6840 .7055 .7282 .7520 .7773

.6655 .6861 .7077 .7305 .7545 .7799

.6676 .6882 .7100 .7328 .7570 .7825

.6696 .6904 .7122 .7352 .7595 .7852

.6716 .6925 .7144 .7375 .7620 .7878

.6737 .6946 .7167 .7399 .7645 .7905

.6757 .6968 .7190 .7423 .7670 .7932

84.0 85.0 86.0 87.0 88.0 89.0

.7959 .8239 .8539 .8861 .9208 .9586

.7986 .8268 .8570 .8894 .9245 .9626

.8013 .8297 .8601 .8928 .9281 .9666

.8041 .8327 .8633 .8962 .9318 .9706

.8069 .8356 .8665 .8996 .9355 .9747

.8097 .8386 .8697 .9031 .9393 .9788

.8125 .8416 .8729 .9066 .9431 .9830

.8153 .8447 .8761 .9101 .9469 .9872

.8182 .8477 .8794 .9136 .9508 .9914

.8210 .8508 .8827 .9172 .9547 .9957

short standard long

DEAN #37261

LEFT

(McGHP)

2.98

INTERACTIVE

top of rh base of rh

SECTION 2

cap height base of text

TABLE 2.21 Transmittance-Absorbance Conversion Table From Meites, Handbook of Analytical Chemistry, 1963, McGraw-Hill Book Company; by permission. This table gives absorbance values to four significant figures corresponding to % transmittance values which are given to three significant figures. The values of % transmittance are given in the left-hand column and in the top row. For example, 8.4% transmittance corresponds to an absorbance of 1.076. Interpolation is facilitated and accuracy is maximized if the % transmittance is between 1 and 10, by multiplying its value by 10, finding the absorbance corresponding to the result, and adding 1. For example, to find the absorbance corresponding to 8.45% transmittance, note that 84.5% transmittance corresponds to an absorbance of 0.0731, so that 8.45% transmittance corresponds to an absorbance of 1.0731. For % transmittance values between 0.1 and 1, multiply by 100, find the absorbance corresponding to the result, and add 2. Conversely, to find the % transmittance corresponding to an absorbance between 1 and 2, subtract 1 from the absorbance, find the % transmittance corresponding to the result, and divide by 10. For example, an absorbance of 1.219 can best be converted to % transmittance by noting that an absorbance of 0.219 would correspond to 60.4% transmittance; dividing this by 10 gives the desired value, 6.04% transmittance. For absorbance values between 2 and 3, subtract 2 from the absorbance, find the % transmittance corresponding to the result, and divide by 100. % Transmittance

0.0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

0 1 2 3 4 5

...... 2.000 1.699 1.523 1.398 1.301

3.000 1.959 1.678 1.509 1.387 1.292

2.699 1.921 1.658 1.495 1.377 1.284

2.523 1.886 1.638 1.481 1.367 1.276

2.398 1.854 1.620 1.469 1.357 1.268

2.301 1.824 1.602 1.456 1.347 1.260

2.222 1.796 1.585 1.444 1.337 1.252

2.155 1.770 1.569 1.432 1.328 1.244

2.097 1.745 1.553 1.420 1.319 1.237

2.046 1.721 1.538 1.409 1.310 1.229

6 7 8 9 10

1.222 1.155 1.097 1.046 1.000

1.215 1.149 1.092 1.041 0.9957

1.208 1.143 1.086 1.036 0.9914

1.201 1.137 1.081 1.032 0.9872

1.194 1.131 1.076 1.027 0.9830

1.187 1.125 1.071 1.022 0.9788

1.180 1.119 1.066 1.018 0.9747

1.174 1.114 1.060 1.013 0.9706

1.167 1.108 1.056 1.009 0.9666

1.161 1.102 1.051 1.004 0.9626

11 12 13 14 15

0.9586 0.9208 0.8861 0.8539 0.8239

0.9547 0.9172 0.8827 0.8508 0.8210

0.9508 0.9136 0.8794 0.8477 0.8182

0.9469 0.9101 0.8761 0.8447 0.8153

0.9431 0.9066 0.8729 0.8416 0.8125

0.9393 0.9031 0.8697 0.8386 0.8097

0.9355 0.8996 0.8665 0.8356 0.8069

0.9318 0.8962 0.8633 0.8327 0.8041

0.9281 0.8928 0.8601 0.8297 0.8013

0.9245 0.8894 0.8570 0.8268 0.7986

16 17 18 19 20

0.7959 0.7696 0.7447 0.7212 0.6990

0.7932 0.7670 0.7423 0.7190 0.6968

0.7905 0.7645 0.7399 0.7167 0.6946

0.7878 0.7620 0.7375 0.7144 0.6925

0.7852 0.7595 0.7352 0.7122 0.6904

0.7825 0.7570 0.7328 0.7100 0.6882

0.7799 0.7545 0.7305 0.7077 0.6861

0.7773 0.7520 0.7282 0.7055 0.6840

0.7747 0.7496 0.7258 0.7033 0.6819

0.7721 0.7471 0.7235 0.7011 0.6799

21 22 23 24 25

0.6778 0.6576 0.6383 0.6198 0.6021

0.6757 0.6556 0.6364 0.6180 0.6003

0.6737 0.6536 0.6345 0.6162 0.5986

0.6716 0.6517 0.6326 0.6144 0.5969

0.6696 0.6498 0.6308 0.6126 0.5952

0.6676 0.6478 0.6289 0.6108 0.5935

0.6655 0.6459 0.6271 0.6091 0.5918

0.6635 0.6440 0.6253 0.6073 0.5901

0.6615 0.6421 0.6234 0.6055 0.5884

0.6596 0.6402 0.6216 0.6038 0.5867

26 27 28 29 30

0.5850 0.5686 0.5528 0.5376 0.5229

0.5834 0.5670 0.5513 0.5361 0.5214

0.5817 0.5654 0.5498 0.5346 0.5200

0.5800 0.5638 0.5482 0.5331 0.5186

0.5784 0.5622 0.5467 0.5317 0.5171

0.5766 0.5607 0.5452 0.5302 0.5157

0.5751 0.5591 0.5436 0.5287 0.5143

0.5735 0.5575 0.5421 0.5272 0.5129

0.5719 0.5560 0.5406 0.5258 0.5114

0.5702 0.5544 0.5391 0.5243 0.5100

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TABLE 2.21 Transmittance-Absorbance Conversion Table (Continued) % Transmittance

0.0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

31 32 33 34 35

0.5086 0.4949 0.4815 0.4685 0.4559

0.5072 0.4935 0.4802 0.4672 0.4547

0.5058 0.4921 0.4789 0.4660 0.4535

0.5045 0.4908 0.4776 0.4647 0.4522

0.5031 0.4895 0.4763 0.4634 0.4510

0.5017 0.4881 0.4750 0.4622 0.4498

0.5003 0.4868 0.4737 0.4609 0.4486

0.4989 0.4855 0.4724 0.4597 0.4473

0.4976 0.4841 0.4711 0.4584 0.4461

0.4962 0.4828 0.4698 0.4572 0.4449

36 37 38 39 40

0.4437 0.4318 0.4202 0.4089 0.3979

0.4425 0.4306 0.4191 0.4078 0.3969

0.4413 0.4295 0.4179 0.4067 0.3958

0.4401 0.4283 0.4168 0.4056 0.3947

0.4389 0.4271 0.4157 0.4045 0.3936

0.4377 0.4260 0.4145 0.4034 0.3925

0.4365 0.4248 0.4134 0.4023 0.3915

0.4353 0.4237 0.4123 0.4012 0.3904

0.4342 0.4225 0.4112 0.4001 0.3893

0.4330 0.4214 0.4101 0.3989 0.3883

41 42 43 44 45

0.3872 0.3768 0.3665 0.3565 0.3468

0.3862 0.3757 0.3655 0.3556 0.3458

0.3851 0.3747 0.3645 0.3546 0.3449

0.3840 0.3737 0.3635 0.3536 0.3439

0.3830 0.3726 0.3625 0.3526 0.3429

0.3820 0.3716 0.3615 0.3516 0.3420

0.3809 0.3706 0.3605 0.3507 0.3410

0.3799 0.3696 0.3595 0.3497 0.3401

0.3788 0.3686 0.3585 0.3487 0.3391

0.3778 0.3675 0.3575 0.3478 0.3382

46 47 48 49 50

0.3372 0.3279 0.3188 0.3098 0.3010

0.3363 0.3270 0.3179 0.3089 0.3002

0.3354 0.3261 0.3170 0.3080 0.2993

0.3344 0.3251 0.3161 0.3072 0.2984

0.3335 0.3242 0.3152 0.3063 0.2976

0.3325 0.3233 0.3143 0.3054 0.2967

0.3316 0.3224 0.3134 0.3045 0.2958

0.3307 0.3215 0.3125 0.3036 0.2950

0.3298 0.3206 0.3116 0.3028 0.2941

0.3288 0.3197 0.3107 0.3019 0.2933

51 52 53 54 55

0.2924 0.2840 0.2757 0.2676 0.2596

0.2916 0.2832 0.2749 0.2668 0.2588

0.2907 0.2823 0.2741 0.2660 0.2581

0.2899 0.2815 0.2733 0.2652 0.2573

0.2890 0.2807 0.2725 0.2644 0.2565

0.2882 0.2798 0.2716 0.2636 0.2557

0.2874 0.2790 0.2708 0.2628 0.2549

0.2865 0.2782 0.2700 0.2620 0.2541

0.2857 0.2774 0.2692 0.2612 0.2534

0.2848 0.2765 0.2684 0.2604 0.2526

56 57 58 59 60

0.2518 0.2441 0.2366 0.2291 0.2218

0.2510 0.2434 0.2358 0.2284 0.2211

0.2503 0.2426 0.2351 0.2277 0.2204

0.2495 0.2418 0.2343 0.2269 0.2197

0.2487 0.2411 0.2336 0.2262 0.2190

0.2480 0.2403 0.2328 0.2255 0.2182

0.2472 0.2396 0.2321 0.2248 0.2175

0.2464 0.2388 0.2314 0.2240 0.2168

0.2457 0.2381 0.2306 0.2233 0.2161

0.2449 0.2373 0.2299 0.2226 0.2154

61 62 63 64 65

0.2147 0.2076 0.2007 0.1938 0.1871

0.2140 0.2069 0.2000 0.1931 0.1864

0.2132 0.2062 0.1993 0.1925 0.1858

0.2125 0.2055 0.1986 0.1918 0.1851

0.2118 0.2048 0.1979 0.1911 0.1844

0.2111 0.2041 0.1972 0.1904 0.1838

0.2104 0.2034 0.1965 0.1898 0.1831

0.2097 0.2027 0.1959 0.1891 0.1824

0.2090 0.2020 0.1952 0.1884 0.1818

0.2083 0.2013 0.1945 0.1878 0.1811

66 67 68 69 70

0.1805 0.1739 0.1675 0.1612 0.1549

0.1798 0.1733 0.1669 0.1605 0.1543

0.1791 0.1726 0.1662 0.1599 0.1537

0.1785 0.1720 0.1656 0.1593 0.1530

0.1778 0.1713 0.1649 0.1586 0.1524

0.1772 0.1707 0.1643 0.1580 0.1518

0.1765 0.1701 0.1637 0.1574 0.1512

0.1759 0.1694 0.1630 0.1568 0.1506

0.1752 0.1688 0.1624 0.1561 0.1500

0.1746 0.1681 0.1618 0.1555 0.1494

71 72 73

0.1487 0.1427 0.1367

0.1481 0.1421 0.1361

0.1475 0.1415 0.1355

0.1469 0.1409 0.1349

0.1463 0.1403 0.1343

0.1457 0.1397 0.1337

0.1451 0.1391 0.1331

0.1445 0.1385 0.1325

0.1439 0.1379 0.1319

0.1433 0.1373 0.1314

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TABLE 2.21 Transmittance-Absorbance Conversion Table (Continued) % Transmittance

0.0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

74 75

0.1308 0.1249

0.1302 0.1244

0.1296 0.1238

0.1290 0.1232

0.1284 0.1226

0.1278 0.1221

0.1273 0.1215

0.1267 0.1209

0.1261 0.1203

0.1255 0.1198

76 77 78 79 80

0.1192 0.1135 0.1079 0.1024 0.0969

0.1186 0.1129 0.1073 0.1018 0.0964

0.1180 0.1124 0.1068 0.1013 0.0958

0.1175 0.1118 0.1062 0.1007 0.0953

0.1169 0.1113 0.1057 0.1002 0.0947

0.1163 0.1107 0.1051 0.0996 0.0942

0.1158 0.1101 0.1046 0.0991 0.0937

0.1152 0.1096 0.1040 0.0985 0.0931

0.1146 0.1090 0.1035 0.0980 0.0926

0.1141 0.1085 0.1029 0.0975 0.0921

81 82 83 84 85

0.0915 0.0862 0.0809 0.0757 0.0706

0.0910 0.0857 0.0804 0.0752 0.0701

0.0904 0.0851 0.0799 0.0747 0.0696

0.0899 0.0846 0.0794 0.0742 0.0691

0.0894 0.0841 0.0788 0.0737 0.0685

0.0888 0.0835 0.0783 0.0731 0.0680

0.0883 0.0830 0.0778 0.0726 0.0675

0.0878 0.0825 0.0773 0.0721 0.0670

0.0872 0.0820 0.0768 0.0716 0.0665

0.0867 0.0814 0.0762 0.0711 0.0660

86 87 88 89 90

0.0655 0.0605 0.0555 0.0506 0.0458

0.0650 0.0600 0.0550 0.0501 0.0453

0.0645 0.0595 0.0545 0.0496 0.0448

0.0640 0.0590 0.0540 0.0491 0.0443

0.0635 0.0585 0.0535 0.0487 0.0438

0.0630 0.0580 0.0531 0.0482 0.0434

0.0625 0.0575 0.0526 0.0477 0.0429

0.0620 0.0570 0.0521 0.0472 0.0424

0.0615 0.0565 0.0516 0.0467 0.0419

0.0610 0.0560 0.0511 0.0462 0.0414

91 92 93 94 95

0.0410 0.0362 0.0315 0.0269 0.0223

0.0405 0.0357 0.0311 0.0264 0.0218

0.0400 0.0353 0.0306 0.0259 0.0214

0.0395 0.0348 0.0301 0.0255 0.0209

0.0391 0.0343 0.0297 0.0250 0.0205

0.0386 0.0339 0.0292 0.0246 0.0200

0.0381 0.0334 0.0287 0.0241 0.0195

0.0376 0.0329 0.0283 0.0237 0.0191

0.0372 0.0325 0.0278 0.0232 0.0186

0.0367 0.0320 0.0273 0.0227 0.0182

96 97 98 99

0.0177 0.0132 0.0088 0.0044

0.0173 0.0128 0.0083 0.0039

0.0168 0.0123 0.0079 0.0035

0.0164 0.0119 0.0074 0.0031

0.0159 0.0114 0.0070 0.0026

0.0155 0.0110 0.0066 0.0022

0.0150 0.0106 0.0061 0.0017

0.0146 0.0101 0.0057 0.0013

0.0141 0.0097 0.0052 0.0009

0.0137 0.0092 0.0048 0.0004

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TABLE 2.22 Wavenumber/Wavelength Conversion Table This table is based on the conversion: wavenumber (in cm⫺1) ⫽ 10 000/wavelength (in ␮m). For example, 15.4 ␮m is equal to 649 cm⫺1. Wavelength (␮m)

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9 cm⫺1

1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 9.0 10.0 11.0 12.0 13.0 14.0 15.0 16.0 17.0 18.0 19.0 20.0 21.0 22.0 23.0 24.0 25.0 26.0 27.0 28.0 29.0 30.0 31.0 32.0 33.0 34.0 35.0 36.0 37.0 38.0 39.0 40.0

10000 5000 3333 2500 2000 1667 1429 1250 1111 1000 909 833 769 714 667 625 588 556 526 500 476 455 435 417 400 385 370 357 345 333 323 313 303 294 286 278 270 263 256 250

9091 4762 3226 2439 1961 1639 1408 1235 1099 990 901 826 763 709 662 621 585 552 524 498 474 452 433 415 398 383 369 356 344 332 322 312 302 293 285 277 270 262 256

8333 4545 3125 2381 1923 1613 1389 1220 1087 980 893 820 758 704 658 617 581 549 521 495 472 450 431 413 397 382 368 355 342 331 321 311 301 292 284 276 269 262 255

7692 4348 3030 2326 1887 1587 1370 1205 1075 971 885 813 752 699 654 613 578 546 518 493 469 448 429 412 395 380 366 353 341 330 319 310 300 292 283 275 268 261 254

7143 4167 2941 2273 1852 1563 1351 1190 1064 962 877 806 746 694 649 610 575 543 515 490 467 446 427 410 394 379 365 352 340 329 318 309 299 291 282 274 267 260 254

6667 4000 2857 2222 1818 1538 1333 1176 1053 952 870 800 741 690 645 606 571 541 513 488 465 444 426 408 392 377 364 351 339 328 317 308 299 290 282 274 267 260 253

6250 3846 2778 2174 1786 1515 1316 1163 1042 943 862 794 735 685 641 602 568 538 510 485 463 442 424 407 391 376 362 350 338 327 316 307 298 289 281 273 266 259 253

5882 3704 2703 2128 1754 1493 1299 1149 1031 935 855 787 730 680 637 599 565 535 508 483 461 441 422 405 389 375 361 348 337 326 315 306 297 288 280 272 265 258 252

5556 3571 2632 2083 1724 1471 1282 1136 1020 926 847 781 725 676 633 595 562 532 505 481 459 439 420 403 388 373 360 347 336 325 314 305 296 287 279 272 265 258 251

5263 3448 2564 2041 1695 1449 1266 1124 1010 917 840 775 719 671 629 592 559 529 503 478 457 437 418 402 386 372 358 346 334 324 313 304 295 287 279 271 264 257 251

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MATHEMATICAL TABLES Logarithms

2.2.1.1 Properties and Uses Definition of Logarithm. The logarithm x of the number N to the base b is the exponent of the power to which b must be raised to give N. That is, logb N ⫽ x

bx ⫽ N

or

The number N is positive and b may be any positive number except 1. Properties of Logarithms 1. The logarithm of a product is equal to the sum of the logarithms of the factors; thus, logb M · N ⫽ logb M ⫹ logb N 2. The logarithm of a quotient is equal to the logarithm of the numerator minus the logarithm of the denominator; thus, logb

M ⫽ logb M ⫺ logb N N

3. The logarithm of a power of a number is equal to the logarithm of the base multiplied by the exponent of the power; thus, logb Mp ⫽ p · logb M 4. The logarithm of a root of a number is equal to the logarithm of the number divided by the index of the root; thus q

logb p M ⫽

1 logb M q

Other properties of logarithms: q

p log b M q

logb b ⫽ 1

logb p Mp ⫽

logb 1 ⫽ 0

logb N ⫽ loga N · logb a ⫽

logb (bN) ⫽ N

loga N loga b

blogbN ⫽ N

Systems of Logarithms. There are two common systems of logarithms in use: (1) the natural (Napierian or hyperbolic) system which uses the base e ⫽ 2.71828 . . . ; (2) the common (Briggsian) system which uses the base 10. We shall use the abbreviation log N ⬅ log10 N in this section. Unless otherwise stated, tables of logarithms are always tables of common logarithms. Characteristic of a Common Logarithm of a Number. Every real positive number has a real common logarithm such that if a ⬍ b, log a ⬍ log b. Neither zero nor any negative number has a real logarithm. A common logarithm, in general, consists of an integer, which is called the characteristic, and a decimal (usually endless), which is called the mantissa. The characteristic of any number may be determined from the following rules:

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Rule I. The characteristic of any number greater than 1 is one less than the number of digits before the decimal point. Rule II.* The characteristic of a number less than 1 is found by subtracting from 9 the number of ciphers between the decimal point and the first significant digit, and writing ⫺10 after the result. Thus the characteristic of log 936 is 2; the characteristic of log 9.36 is 0; of log 0.936 is 9 ⫺ 10; of log 0.00936 is 7 ⫺ 10. Mantissa of a Common Logarithm of a Number. An important consequence of the use of base 10 is that the mantissa of a number is independent of the position of the decimal point. Thus 93 600, 93.600, 0.000 936, all have the same mantissa. Hence in Tables of Common Logarithms only mantissas are given. A five-place table gives the values of the mantissa correct to five places of decimals. Since it is possible to obtain logarithms by using hand calculators, this Handbook contains no logarithm tables. Helpful Hints

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1. When connecting numbers to logarithms, use as many decimal places in the mantissa as there are significant digits in the number. 2. When finding the antilogarithm, keep as many significant digits as there are decimal places in the mantissa. Examples: log 10.35 ⫽ 1.0149; antilog 0.065 ⫽ 1.16.

* Some writers use a dash over the characteristic to indicate a negative value; for example, log 0.004657 ⫽ 7.6681 ⫺ 10 ⫽ 3.6681

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TABLE 2.23 Derivatives and Differentiation

Rules for differentiation. From Baumeister and Marks, Standard Handbook for Mechanical Engineers, 7th ed., McGraw-Hill Book Company, New York (1967); by permission. To find the derivative of a given function at a given point: (1) If the function is given only by a curve, measure graphically the slope of the tangent at the point in question; (2) if the function is given by a mathematical expression, use the following rules for differentiation. These rules give, directly, the differential, dy, in terms of dx; to find the derivative, dy/dx, divide through by dx. Here u, v, w, . . . represents any functions of a variable x, or may themselves be independent variables. a is a constant which does not change in values in the same discussion; e ⫽ 2.71828. 1. d(a ⫹ u) ⫽ du 3. d(u ⫹ v ⫹ w ⫹ · · ·) ⫽ du ⫹ dv ⫹ dw ⫹ · · · 4. d(uv) ⫽ u dv ⫹ v du du dv dw 5. d(uvw . . .) ⫽ (uvw . . .) ⫹ ⫹ ⫹ ··· u v w u v du ⫺ u dv 6. d ⫽ v v2 Thus, d(u2) ⫽ 2u du 8. d p u ⫽ 2 pu 10. d(eu) ⫽ eu du du 12. d ln u ⫽ u 14. d sin u ⫽ cos u du 16. d cos u ⫽ ⫺sin u du 18. d tan u ⫽ sec2 u du du 20. d sin⫺1 u ⫽ 2 p1 ⫺ u du 22. d cos⫺1 u ⫽ ⫺ 2 p1 ⫺ u du 24. d tan⫺1 u ⫽ 1 ⫹ u2

冉

26. d ln sin u ⫽ cot u du

2. d(au) ⫽ a du

冊 7. d(um) ⫽ mum ⫺ 1 du du; d(u3) ⫽ 3u2 du; etc. 1 du 9. d ⫽⫺ 2 u u 11. d(au) ⫽ (ln a)au du

冉冊

du du ⫽ (0.4343 . . .) u u d csc u ⫽ ⫺cot u csc u du d sec u ⫽ tan u sec u du d cot u ⫽ ⫺csc2 u du du d csc⫺1 u ⫽ ⫺ u p u2 ⫺ 1 du d sec⫺1 u ⫽ u p u2 ⫺ 1 du d cot⫺1 u ⫽ ⫺ 1 ⫹ u2 2 du d ln tan u ⫽ sin 2u 2 du d ln cot u ⫽ ⫺ sin 2u d csch u ⫽ ⫺csch u coth u du d sech u ⫽ ⫺sech u tanh u du d coth u ⫽ ⫺csch2 u du du d csch⫺1 u ⫽ ⫺ u p u2 ⫹ 1 du d sech⫺1 u ⫽ ⫺ u p 1 ⫺ u2 du d coth⫺1 u ⫽ 1 ⫺ u2

13. d log10 u ⫽ (log10 e) 15. 17. 19. 21. 23. 25. 27.

28. d ln cos u ⫽ ⫺tan u du

29.

30. d sinh u ⫽ cosh u du 32. d cosh u ⫽ sinh u du 34. d tanh u ⫽ sech2 u du du 36. d sinh⫺1 u ⫽ 2 pu ⫹ 1 du 38. d cosh⫺1 u ⫽ 2 pu ⫺ 1 du 40. d tanh⫺1 u ⫽ 1 ⫺ u2 42. d(uv) ⫽ (uv ⫺ 1)(u ln u dv ⫹ v du)

31. 33. 35. 37. 39. 41.

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TABLE 2.24 Integrals From Baumeister and Marks, Standard Handbook for Mechanical Engineers, 7th ed., McGraw-Hill Book Company, New York (1967); by permission. An integral of f(x) dx is any function whose differential is f(x) dx, and is denoted by 兰 f(x) dx. All the integrals of f(x) dx are included in the expression 兰 f(x) dx ⫹ C, where 兰 f(x) dx is any particular integral, and C is an arbitrary constant. The process of finding (when possible) an integral of a given function consists in recognizing by inspection a function which, when differentiated, will produce the given function; or in transforming the given function into a form in which such recognition is easy. The most common integrable forms are collected in the following brief table; for a more extended list, see Peirce, Table of Integrals, Ginn, or Dwight, Table of Integrals and other Mathematical Data, Macmillan. General formulas 1. 3. 5.

冕 冕 冕 冕 冕 冕 冕 冕 a du ⫽ a

du ⫽ au ⫹ C

u dv ⫽ uv ⫺ dy

2.

v du

f (x, y) dx ⫽

dx

4.

冕 冕

(u ⫹ v) dx ⫽

冕

f (x) dx ⫽

f [F(y)]F⬘(y) dy, x ⫽ F(y)

冕

u dx ⫹

冕

v dx

f (x, y) dy Fundamental integrals

6. 7. 9. 11. 13. 14.

冕 冕 冕 冕 冕 冕

x n dx ⫽

x n⫹1 ⫹ C, when n ⫽ ⫺1 n⫹1

dx ⫽ ln x ⫹ C ⫽ ln cx x

8.

sin x dx ⫽ ⫺cos x ⫹ C

10.

dx ⫽ ⫺cot x ⫹ C sin2 x dx ⫽ sin⫺1 x ⫹ C ⫽ ⫺cos⫺1 x ⫹ c 2 p1 ⫺ x dx ⫽ tan⫺1 x ⫹ C ⫽ ⫺cot ⫺1 x ⫹ c 1 ⫹ x2

12.

冕 冕 冕

ex dx ⫽ ex ⫹ C cos x dx ⫽ sin x ⫹ C dx ⫽ tan x ⫹ C cos2 x

Rational functions 15. 16. 17. 19. 20. 21. 22.

冕 冕 冕 冕 冕 冕 冕

(a ⫹ bx)n⫹1 ⫹C (n ⫹ 1)b dx 1 1 ⫽ ln(a ⫹ bx) ⫹ C ⫽ ln c(a ⫹ bx) a ⫹ bx b b 1 1 dx 1 dx ⫽ ⫺ ⫹ C 18. ⫽⫺ ⫹C x2 x (a ⫹ bx)2 b(a ⫹ bx) dx 1⫹x ⫽ 1⁄2 ln ⫹ C ⫽ tanh⫺1 x ⫹ C, when x ⬍ 1 1 ⫺ x2 1⫺x dx x⫺1 ⫽ 1⁄2 ln ⫹ C ⫽ ⫺coth⫺1 x ⫹ C, when x ⬎ 1 x2 ⫺ 1 x⫹1 dx 1 b ⫽ tan⫺1 x ⫹C a ⫹ bx2 p ab a

(a ⫹ bx)n dx ⫽

冕

冉q 冊

dx 1 p ab ⫹ bx ⫽ ln ⫹C a ⫺ bx2 2 p ab p ab ⫺ bx 1 b ⫽ tanh⫺1 x ⫹C a p ab

冉q 冊

冎

[a ⬎ 0, b ⬎ 0]

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TABLE 2.24 Integrals (Continued) Rational functions (continued)

冕

冎

dx 1 b ⫹ cx ⫽ tan⫺1 ⫹ C [ac ⫺ b2 ⬎ 0] 2 a ⫹ 2bx ⫹ cx2 p ac ⫺ b2 p ac ⫺ b 2 1 p b ⫺ ac ⫺ b ⫺ cx ⫽ ln ⫹C 2 p b2 ⫺ ac p b2 ⫺ ac ⫹ b ⫹ cx [b2 ⫺ ac ⬎ 0] 1 b ⫹ cx ⫽⫺ tanh⫺1 ⫹C 2 2 p b ⫺ ac p b ⫺ ac dx 1 24. ⫽⫺ ⫹ C, when b2 ⫽ ac a ⫹ 2bx ⫹ cx2 b ⫹ cx (m ⫹ nx) dx n mc ⫺ nb dx 25. ⫽ ln (a ⫹ 2bx ⫹ cx2) ⫹ a ⫹ 2bx ⫹ cx2 2c c a ⫹ 2bx ⫹ cx2 f (x) dx 26. In , if f (x) is a polynomial of higher than the first degree, divide a ⫹ 2bx ⫹ cx2 by the denominator before integrating. dx 1 b ⫹ cx 27. ⫽ ⫻ (a ⫹ 2bx ⫹ cx2) p 2(ac ⫺ b2)(p ⫺ 1) (a ⫹ 2bx ⫹ cx2) p ⫺ 1 23.

冕 冕

冕

冕

冕

28.

冕 冕

冕

(2p ⫺ 3)c dx 2(ac ⫺ b2)(p ⫺ 1) (a ⫹ 2bx ⫹ cx2) p ⫺ 1 (m ⫹ nx) dx n 1 ⫽⫺ ⫻ (a ⫹ 2bx ⫹ cx2) p 2c(p ⫺ 1) (a ⫹ 2bx ⫹ cx2) p ⫺ 1 ⫹

⫹ 29.

冎

x m ⫺ 1(a ⫹ bx)n dx ⫽ ⫽

mc ⫺ nb c

冕

dx (a ⫹ 2bx ⫹ cx2) p

x m ⫺ 1(a ⫹ bx)n⫹1 (m ⫺ 1)a ⫺ (m ⫹ n)b (m ⫹ n)b x m(a ⫹ bx)n na ⫹ m⫹n m⫹n

冕

冕

x m ⫺ 2(a ⫹ bx)n dx

xm ⫺ 1(a ⫹ bx)n ⫺ 1 dx

Irrational functions 30. 32. 33. 34. 35. 36. 37.

冕 冕 冕 冕 冕 冕 冕

冕

2 dx 2 3 31. ⫽ p a ⫹ bx ⫹ C p (a ⫹ bx) ⫹ C 3b b a ⫹ bx p (m ⫹ nx) dx 2 ⫽ 2 (3mb ⫺ 2an ⫹ nbx) p a ⫹ bx ⫹ C 3b p a ⫹ bx dx ; substitute y ⫽ p a ⫹ bx, and use 21 and 22 (m ⫹ nx) p a ⫹ bx

p a ⫹ bx dx ⫽

n f (x, p a ⫹ bx) n dx; substitute p a ⫹ bx ⫽ y n F(x, p a ⫹ bx) dx x x ⫽ sin⫺1 ⫹ C ⫽ ⫺cos⫺1 ⫹ c 2 2 a a pa ⫺ x dx x ⫽ ln (x ⫹ p a2 ⫹ x2) ⫹ C ⫽ sinh⫺1 ⫹ c 2 2 a a ⫹ x p dx x ⫽ ln (x ⫹ p x2 ⫺ a2) ⫹ C ⫽ cosh⫺1 ⫹ c 2 2 a px ⫺ a

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2.107

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TABLE 2.24 Integrals (Continued) Irrational functions (continued) 38.

冕

dx 2 p a ⫹ 2bx ⫹ cx

⫽ ⫽ ⫽

39. 40.

41.

42. 43.

44.

冕 冕 冕 冕 冕 冕

1 pc

1

pc

1

pc

ln (b ⫹ cx ⫹ p c p a ⫹ 2bx ⫹ cx2) ⫹ C, when c ⬎ 0 sinh⫺1 cosh⫺1

⫹ C, when ac ⫺ b2 ⬎ 0

2 p ac ⫺ b

b ⫹ cx

2 p b ⫺ ac

⫹ C, when b2 ⫺ ac ⬎ 0

b ⫹ cx sin⫺1 ⫹ C, when c ⬍ 0 2 ⫺c p p b ⫺ ac (m ⫹ nx) dx n mc ⫺ nb dx ⫽ p a ⫹ 2bx ⫹ cx2 ⫹ 2 2 c c p a ⫹ 2bx ⫹ cx p a ⫹ 2bx ⫹ cx ⫽

x m dx p a ⫹ 2bx ⫹ cx

2

⫽

⫺1

b ⫹ cx

x m ⫺ 1 X (m ⫺ 1)a ⫺ mc mc

冕

冕

x m ⫺ 2 dx (2m ⫺ 1)b ⫺ X mc

冕

x m ⫺ 1 dx , X

when X ⫽ p a ⫹ 2bx ⫹ cx2 x a2 2 2 2 2 ln (x ⫹ p a2 ⫹ x2) ⫹ C p a ⫹ x dx ⫽ p a ⫹ x ⫹ 2 2 x a2 x ⫽ p a2 ⫹ x2 ⫹ sinh⫺1 ⫹ c 2 2 a x a2 ⫺1 x 2 2 2 2 sin ⫹C p a ⫺ x dx ⫽ p a ⫺ x ⫹ 2 2 a 2 x a 2 2 2 2 ln (x ⫹ p x2 ⫺ a2) ⫹ C p x ⫺ a dx ⫽ p x ⫺ a ⫺ 2 2 x a2 x ⫽ p x2 ⫺ a2 ⫺ cosh⫺1 ⫹ c 2 2 a b ⫹ cx 2 2 p a ⫹ 2bx ⫹ cx dx ⫽ p a ⫹ 2bx ⫹ cx 2c ac ⫺ b2 dx ⫹ ⫹C 2 2c p a ⫹ 2bx ⫹ cx

冕

Transcendental functions 45. 46. 47. 48. 49. 50. 51. 52.

冕 冕 冕 冕 冕 冕 冕 冕

ax ⫹C ln a x neax n n(n ⫺ 1) n! x neax dx ⫽ 1⫺ ⫹ ⫺ ··· ⫾ n n a ax a2x2 ax ax dx ⫽

冋

册

⫹C

ln x dx ⫽ x ln x ⫺ x ⫹ C ln x ln x 1 dx ⫽ ⫺ ⫺ ⫹C x2 x x (ln x)n 1 dx ⫽ (ln x)n ⫹ 1 ⫹ C x n⫹1 sin2 x dx ⫽ ⫺ 1⁄4 sin 2x ⫹ 1⁄2x ⫹ C ⫽ ⫺ 1⁄2 sin x cos x ⫹ 1⁄2x ⫹ C cos2 x dx ⫽ 1⁄4 sin 2x ⫹ 1⁄2x ⫹ C ⫽ 1⁄2 sin x cos x ⫹ 1⁄2x ⫹ C sin mx dx ⫽ ⫺

cos mx ⫹C m

53.

冕

cos mx dx ⫽

sin mx ⫹C m

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TABLE 2.24 Integrals (Continued) Transcendental functions (continued)

冕 冕 冕 冕 冕 冕 冕 冕 冕 冕 冕 冕 冕 冕

cos(m ⫹ n)x cos(m ⫺ n)x ⫺ ⫹C 2(m ⫹ n) 2(m ⫺ n)

sin mx cos nx dx ⫽ ⫺

54.

sin mx sin nx dx ⫽

55.

sin(m ⫺ n)x sin(m ⫹ n)x ⫺ ⫹C 2(m ⫺ n) 2(m ⫹ n)

cos mx cos nx dx ⫽

56.

sin(m ⫺ n)x sin(m ⫹ n)x ⫹ ⫹C 2(m ⫺ n) 2(m ⫹ n)

tan x dx ⫽ ⫺ln cos x ⫹ C

57. 59. 61.

65.* 66.* 67. 68. 69.

62. 64.

冕 冕

cos x sinn ⫺ 1 x n ⫺ 1 ⫹ sinn ⫺ 2 x dx n n sin x cosn ⫺ 1 x n ⫺ 1 cosn x dx ⫽ ⫹ cosn ⫺ 2 x dx n n tann ⫺ 1 x tann x dx ⫽ ⫺ tann ⫺ 2 x dx n⫺1 cotn ⫺ 1 x cotn x dx ⫽ ⫺ ⫺ cotn ⫺ 2 x dx n⫺1 dx cos x n⫺2 dx ⫽⫺ ⫹ sinn x (n ⫺ 1) sinn ⫺ 1 x n ⫺ 1 sinn ⫺ 2 x sinn x dx ⫽ ⫺

冕 冕

dx sin x n⫺2 ⫽ ⫹ cosn x (n ⫺ 1) cosn ⫺ 1 x n ⫺ 1

70. 71.*

sin p x cosq x dx ⫽

72.* 73.*

冕 冕 冕

冕 冕

sin p ⫺ 1 x cos q ⫹ 1 p ⫺ 1 ⫹ p⫹q p⫹q

sin⫺p x cos q x dx ⫽ ⫺ sin p x cos⫺q x dx ⫽

冕 冕 冕 冕

cot x dx ⫽ ln sin x ⫹ C

冉 冊

dx ␲ x ⫽ ln tan ⫹ ⫹C cos x 4 2 dx x ⫽ ⫺cot ⫹ C 1 ⫺ cos x 2 dx ⫽ ln tan x ⫹ C sin x cos x

dx cosn ⫺ 2 x

sin p ⫹ 1 x cos q ⫺ 1 x q ⫺ 1 ⫹ p⫹q p⫹q

⫽⫺

冕 冕

sin p x cos q ⫺ 2 x dx sin p ⫺ 2 x cos q x dx

冕 冕

sin⫺p ⫹ 1 x cosq ⫹ 1 x p ⫺ q ⫺ 2 ⫹ p⫺1 p⫺1

sin p ⫹ 1 x cos⫺q ⫹ 1 x q ⫺ p ⫺ 2 ⫹ q⫺1 q⫺1

冉q

冊

sin⫺p ⫹ 2 x cos q x dx

sin p x cos⫺q ⫹ 2 x dx

dx 2 a⫺b ⫽ tan⫺1 tan 1⁄2x ⫹ C, when a2 ⬎ b2 a ⫹ b cos x p a2 ⫺ b2 a⫹b 1 b ⫹ a cos x ⫹ sin x p b2 ⫺ a2 ⫽ ln ⫹C 2 2 a ⫹ b cos x pb ⫺ a [a2 ⬍ b2] ⫽

75.

60.

sin x cos x dx ⫽ 1⁄2 sin2 x ⫹ C

63.

74.

58.

dx x ⫽ ln tan ⫹ C sin x 2 dx x ⫽ tan ⫹ C 1 ⫹ cos x 2

冕

2 2 2 pb ⫺ a

cos x dx x a ⫽ ⫺ a ⫹ b cos x b b

冕

tanh⫺1

冉q

冊

b⫺a tan 1⁄2x b⫹a

⫹C

冎

dx ⫹C a ⫹ b cos x

* If n, p, or q is an odd number, substitute cos x ⫽ z or sin x ⫽ z

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TABLE 2.24 Integrals (Continued) Transcendental functions (continued) 76. 77.

冕 冕

sin x dx 1 ⫽ ⫺ ln (a ⫹ b cos x) ⫹ C a ⫹ b cos x b A ⫹ B cos x ⫹ C sin x dx ⫽ A a ⫹ b cos x ⫹ c sin x

⫹ (B cos u ⫹ C sin u)

冕

冕

dy a ⫹ p cos y

cos y dy ⫺ (B sin u ⫺ C cos u) a ⫹ p cos y

冕

sin y dy , a ⫹ p ⫹ cos y

where b ⫽ p cos u, c ⫽ p sin u, and x ⫺ u ⫽ y

78. 79. 80. 81. 82. 83. 84. 86. 88. 90. 91. 92.

冕 冕 冕 冕 冕 冕 冕 冕 冕 冕 冕 冕

2.2.2

eax sin bx dx ⫽

a sin bx ⫺ b cos bx ax e ⫹C a2 ⫹ b 2

eax cos bx dx ⫽

a cos bx ⫹ b sin bx ax e ⫹C a2 ⫹ b 2

sin⫺1 x dx ⫽ x sin⫺1 x ⫹ p 1 ⫺ x2 ⫹ C cos⫺1 x dx ⫽ x cos⫺1 x ⫺ p 1 ⫺ x2 ⫹ C tan⫺1 x dx ⫽ x tan⫺1 x ⫺ 1⁄2 ln(1 ⫹ x2) ⫹ C cot⫺1 x dx ⫽ x cot⫺1 x ⫹ 1⁄2 ln(1 ⫹ x2) ⫹ C sinh x dx ⫽ cosh x ⫹ C

85.

cosh x dx ⫽ sinh x ⫹ C

87.

sech x dx ⫽ 2 tan⫺1 (ex) ⫹ C

89.

冕 冕 冕

tanh x dx ⫽ ln cosh x ⫹ C coth x dx ⫽ ln sinh x ⫹ C csch x dx ⫽ ln tanh

冉冊 x 2

⫹C

sinh2 x dx ⫽ 1⁄2 sinh x cosh x ⫺ 1⁄2x ⫹ C cosh2 x dx ⫽ 1⁄2 sinh x cosh ⫹ 1⁄2x ⫹ C sech2 x dx ⫽ tanh x ⫹ C

93.

冕

csch2 x dx ⫽ ⫺coth x ⫹ C

Surface Areas and Volumes*

Let a, b, c, d, and s denote lengths, A denote areas, and V denote volumes. Triangle. A ⫽ bh/2, where b denotes the base and h the altitude. Rectangle. A ⫽ ab, where a and b denote the lengths of the sides. Parallelogram (opposite sides parallel). A ⫽ ah ⫽ ab sin ␪, where a and b denote the sides, h the altitude, and ␪ the angle between the sides. Trapezoid (four sides, two parallel). A ⫽ 1⁄2h(a ⫹ b), where a and b are the sides and h the altitude.

* Adapted by permission from Burington, Handbook of Mathematical Tables and Formulas, 3d. ed., McGraw-Hill Book Company, New York (1959).

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Regular Polygon of n Sides (Fig. 2.1) A⫽

1 2 180⬚ na ctn 4 n

R⫽

a 180⬚ csc 2 n

where R is radius of circumscribed circle

r⫽

a 180⬚ ctn 2 n

where r is radius of inscribed circle

␣⫽

360⬚ 2␲ ⫽ radians n n

␤⫽

冉 冊 n⫺2 n

a ⫽ 2r tan

where a is length of side

· 180⬚ ⫽

FIGURE 2.1

冉 冊 n⫺2 n

␲ radians

where ␣ and ␤ are the angles indicated in Fig. 2.1

␣ ␣ ⫽ 2R sin 2 2

Circle (Fig. 2.2). Let C ⫽ circumference

S ⫽ length of arc subtended by ␪

R ⫽ radius

l ⫽ chord subtended by arc S

D ⫽ diameter

h ⫽ rise

A ⫽ area

␪ ⫽ central angle in radians

C ⫽ 2␲R ⫽ ␲D

␲ ⫽ 3.14159 . . .

S ⫽ R␪ ⫽ 1⁄2D␪ ⫽ D cos⫺1

d R

␪ ␪ l ⫽ 2p R2 ⫺ d 2 ⫽ 2R sin ⫽ 2d tan 2 2 d ⫽ 1⁄2p 4R2 ⫺ l2 ⫽ R cos

␪ 1 ␪ ⫽ ⁄2l ctn 2 2

FIGURE 2.2

h⫽R⫺d

␪⫽

S 2S d l l ⫽ ⫽ 2 cos⫺1 ⫽ 2 tan⫺1 ⫽ 2 sin⫺1 R D R 2d D

A (circle) ⫽ ␲R2 ⫽ 1⁄4␲D2 A (sector) ⫽ 1⁄2Rs ⫽ 1⁄2R2␪ A (segment) ⫽ A (sector) ⫺ A (triangle) ⫽ 1⁄2R2 (␪ ⫺ sin ␪) ⫽ R2 cos⫺1

R⫺h ⫺ (R ⫺ h)p 2Rh ⫺ h2 R

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GENERAL INFORMATION, CONVERSION TABLES, AND MATHEMATICS

Perimeter of n-sided regular polygon inscribed in a circle ⫽ 2nR sin Area of inscribed polygon ⫽ 1⁄2nR2 sin

␲ n

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2␲ n

Perimeter of n-sided regular polygon circumscribed about a circle ⫽ 2nR tan Area of circumscribed polygon ⫽ nR2 tan

␲ n

␲ n

Radius of circle inscribed in a triangle of sides a, b, and c is r⫽

q

(s ⫺ a)(s ⫺ b)(s ⫺ c) s

s ⫽ 1⁄2(a ⫹ b ⫹ c)

Radius of circle circumscribed about a triangle is R⫽

abc 4p s(s ⫺ a)(s ⫺ b)(s ⫺ c)

Ellipse (Fig. 2.3). A ⫽ ␲ab, where a and b are lengths of semimajor and semiminor axes, respectively. Parabola (Fig. 2.4) A⫽

2ld 3 FIGURE 2.3

d Height of d1 ⫽ 2 (l 2 ⫺ l 21) l Width of l1 ⫽ l Length of arc ⫽ l

q

d ⫺ d1 d

冋 冉冊 冉冊 1⫹

2 2d 3 l

2

⫺

2 2d 5 l

4

册

⫹ ···

FIGURE 2.4

Area by Approximation (Fig. 2.5). If y0 , y1 , y2 , . . . , yn are the length of a series of equally spaced parallel chords, and if h is their distance apart, the area enclosed by the boundary is given approximately by any one of the following formulae: AT ⫽ h[1⁄2(y0 ⫹ yn) ⫹ y1 ⫹ y2 ⫹ · · · ⫹ yn⫺ 1]

FIGURE 2.5

(Trapezoidal Rule)

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AD ⫽ h[0.4(y0 ⫹ yn) ⫹ 1.1(y1 ⫹ yn⫺ 1) ⫹ y2 ⫹ y3 ⫹ · · · ⫹ yn⫺ 2]

(Durand’s Rule)

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AS ⫽ 1⁄3h[(y0 ⫹ yn) ⫹ 4(y1 ⫹ y3 ⫹ · · · ⫹ yn⫺ 1) ⫹ 2(y2 ⫹ y4 ⫹ · · · ⫹ yn⫺ 2)] (n even, Simpson’s Rule) In general, AS gives the most accurate approximation. The greater the value of n, the greater the accuracy of approximation. Cube. V ⫽ a3; d ⫽ ap 2; total surface area ⫽ 6a2, where a is length of side and d is length of diagonal. Rectangular Parallelopiped. V ⫽ abc; d ⫽ p a2 ⫹ b2 ⫹ c2; total surface area ⫽ 2(ab ⫹ bc ⫹ ca), where a, b, and c are the lengths of the sides and d is length of diagonal. Prism or Cylinder V ⫽ (area of base) · (altitude) Lateral area ⫽ (perimeter of right section) · (lateral edge) Pyramid or Cone V ⫽ 1⁄3(area of base) · (altitude) Lateral area of regular pyramid ⫽ 1⁄2(perimeter of base) · (slant height) Frustum of Pyramid or Cone. V ⫽ 1⁄3(A1 ⫹ A2 ⫹ p A1 · A2)h, where h is the altitude and A1 and A2 are the areas of the bases. Lateral area of a regular figure ⫽ 1⁄2(sum of perimeters of base) · (slant height) Prismoid V⫽

h (A1 ⫹ A2 ⫹ 4A3) 6

where h ⫽ altitude, A1 and A2 are the areas of the bases, and A3 is the area of the midsection parallel to bases. Area of Surface and Volume of Regular Polyhedra of Edge l

Name

Type of surface

Area of surface

Volume

Tetrahedron Hexahedron (cube) Octahedron Dodecahedron Icosahedron

4 equilateral triangles 6 squares 8 equilateral triangles 12 pentagons 20 equilateral triangles

1.73205l 2 6.00000l 2 3.46410l 2 20.64578l 2 8.66025l 2

0.11785l 3 1.00000l 3 0.47140l 3 7.66312l 3 2.18170l 3

Sphere (Fig. 2.6) A (sphere) ⫽ 4␲R2 ⫽ ␲D2 A (zone) ⫽ 2␲Rh1 ⫽ ␲Dh1 V (sphere) ⫽ 4⁄3␲R3 ⫽ 1⁄8␲D3

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V (spherical sector) ⫽ 2⁄3␲R2h1 ⫽ 1⁄6␲D2h1 V (spherical segment of one base) ⫽ 1⁄6␲h3(3r32 ⫹ h32) V (spherical segment of two bases) ⫽ 1⁄6␲h2(3r23 ⫹ 3r22 ⫹ h22) A (lune) ⫽ 2R2␪

where ␪ is angle in radians of lune

Ellipsoid. V ⫽ 4⁄3␲abc, where a, b, and c are the lengths of the semiaxes. Torus (Fig. 2.7) V ⫽ 2␲2Rr2

FIGURE 2.6

Area of surface ⫽ S ⫽ 4␲ Rr 2

2.2.3

Trigonometric Functions of an Angle ␣

Let x be any angle whose initial side lies on the positive x axis and whose vertex is at the origin, and (x, y) be any point on the terminal side of the angle. (x is positive if measured along OX to the right, from the y axis; and negative, if measured along OX⬘ to the left from the y axis. Likewise, y is positive if measured parallel to OY, and negative if measured parallel to OY⬘.) Let r be the positive distance from the origin to the point. The trigonometric functions of an angle are defined as follows: sine ␣

⫽ sin ␣

⫽

y r

cosine ␣

⫽ cos ␣

⫽

x r

⫽ tan ␣

⫽

y x

cotangent ␣ ⫽ ctn ␣

⫽ cot ␣ ⫽

x y

⫽ sec ␣

⫽

r x

cosecant x ⫽ csc ␣

⫽

r y

exsecant x ⫽ exsec ␣

⫽ sec ␣ ⫺ 1

versine ␣

⫽ 1 ⫺ cos ␣

tangent ␣

secant ␣

⫽ vers ␣

coversine ␣ ⫽ covers ␣

⫽ 1 ⫺ sin ␣

haversine ␣ ⫽ hav ␣

⫽ 1⁄2 vers ␣

FIGURE 2.7

FIGURE 2.8

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2.2.3.1

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Signs of the Functions

Quadrant

sin

cos

tan

ctn

sec

csc

I II III IV

⫹ ⫹ ⫺ ⫺

⫹ ⫺ ⫺ ⫹

⫹ ⫺ ⫹ ⫺

⫹ ⫺ ⫹ ⫺

⫹ ⫺ ⫺ ⫹

⫹ ⫹ ⫺ ⫺

2.2.3.2

Relations between the Functions of a Single Angle* sin2 x ⫹ cos2 x ⫽ 1 tan x ⫽

sin x cos x

cot x ⫽

1 cos x ⫽ tan x sin x

1 ⫹ tan2 x ⫽ sec2 x ⫽

1 cos2 x

1 ⫹ cot2 x ⫽ csc2 x ⫽

1 sin2 x

sin x ⫽ p 1 ⫺ cos2 x ⫽ cos x ⫽ p 1 ⫺ sin2 x ⫽

FIGURE 2.9

tan x p 1 ⫹ tan x 2

1 2 p 1 ⫹ tan x

⫽ ⫽

1 2 p 1 ⫹ cot x

cot x 2 p 1 ⫹ cot x

2.2.3.3 Functions of Negative Angles. sin(⫺x) ⫽ ⫺sin x; cos(⫺x) ⫽ cos x; tan(⫺x) ⫽ ⫺tan x. 2.2.3.4

Functions of the Sum and Difference of Two Angles sin(x ⫹ y) ⫽ sin x cos y ⫹ cos x sin y cos(x ⫹ y) ⫽ cos x cos y ⫺ sin x sin y tan(x ⫹ y) ⫽

tan x ⫹ tan y 1 ⫺ tan x tan y

cot(x ⫹ y) ⫽

cot x cot y ⫺ 1 cot x ⫹ cot y

sin(x ⫺ y) ⫽ sin x cos y ⫺ cos x sin y * From Baumeister and Marks, Standard Handbook for Mechanical Engineers, 7th ed., McGraw-Hill Book Company, New York (1967); by permission.

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cos(x ⫺ y) ⫽ cos x cos y ⫹ sin x sin y tan(x ⫺ y) ⫽

tan x ⫺ tan y 1 ⫹ tan x tan y

cot(x ⫺ y) ⫽

cot x cot y ⫹ 1 cot y ⫺ cot x

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sin x ⫹ sin y ⫽ 2 sin 1⁄2(x ⫹ y) cos 1⁄2(x ⫺ y) sin x ⫺ sin y ⫽ 2 cos 1⁄2(x ⫹ y) sin 1⁄2(x ⫺ y) cos x ⫹ cos y ⫽ 2 cos 1⁄2(x ⫹ y) cos 1⁄2(x ⫺ y) cos x ⫺ cos y ⫽ ⫺2 sin 1⁄2(x ⫹ y) sin 1⁄2(x ⫺ y) tan x ⫹ tan y ⫽

sin(x ⫹ y) cos x cos y

cot x ⫹ cot y ⫽

sin(x ⫹ y) sin x sin y

tan x ⫺ tan y ⫽

sin(x ⫺ y) cos x cos y

cot x ⫺ cot y ⫽

sin(y ⫺ x) sin x sin y

sin2 x ⫺ sin2 y ⫽ cos2 y ⫺ cos2 x ⫽ sin(x ⫹ y) sin(x ⫺ y) cos2 x ⫺ sin2 y ⫽ cos2 y ⫺ sin2 x ⫽ cos(x ⫹ y) cos(x ⫺ y) sin(45⬚ ⫹ x) ⫽ cos(45⬚ ⫺ x)

tan(45⬚ ⫹ x) ⫽ cot(45⬚ ⫺ x)

sin(45⬚ ⫺ x) ⫽ cos(45⬚ ⫹ x)

tan(45⬚ ⫺ x) ⫽ cot(45⬚ ⫹ x)

In the following transformations, a and b are supposed to be positive, c ⫽ p a2 ⫹ b2, A ⫽ the positive acute angle for which B ⫽ b/a: a cos x ⫹ b sin x ⫽ c sin(A ⫹ x) ⫽ c cos(B ⫺ x) a cos x ⫺ b sin x ⫽ c sin(A ⫺ x) ⫽ c cos(B ⫹ x)

2.2.4

Expansion in Series*

The range of values of x for which each of the series is convergent is stated at the right of the series. 2.2.4.1

Exponential and Logarithmic Series ex ⫽ 1 ⫹

x x2 x3 x4 ⫹ ⫹ ⫹ ⫹ ··· 1! 2! 3! 4!

ax ⫽ emx ⫽ 1 ⫹

(⫺⬁ ⬍ x ⬍ ⫹⬁)

m m2 2 m3 3 x⫹ x ⫹ x ⫹ ··· 1! 2! 3!

(a ⬎ 0, ⫺⬁ ⬍ x ⬍ ⫹⬁)

where m ⫽ ln a ⫽ 2.3026 log10 a.

* From Baumeister and Marks, Standard Handbook for Mechanical Engineers, 7th ed., McGraw-Hill Book Company, New York (1967); by permission.

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ln(1 ⫹ x) ⫽ x ⫺

x2 x3 x4 x5 ⫹ ⫺ ⫹ ··· 2 3 4 5

ln(1 ⫺ x) ⫽ ⫺x ⫺

冉 冊 冉 冉 冊 冉 冋

x2 x3 x4 x5 ⫺ ⫺ ⫺ ⫺ ··· 2 3 4 5

ln

1⫹x 1⫺x

⫽2 x⫹

ln

x⫹1 x⫺1

⫽2

ln x ⫽ 2

冊

x3 x5 x7 ⫹ ⫹ ⫹ ··· 3 5 7

(⫺1 ⬍ x ⬍ ⫹1) (⫺1 ⬍ x ⬍ ⫹1)

冊 冉 冊 冉 冊 册 冋 冉 冊 冉 冊

1 1 1 1 ⫹ ⫹ ⫹ ⫹ ··· x 3x3 5x5 7x7 x⫺1 1 x⫺1 ⫹ x⫹1 3 x⫹1

ln(a ⫹ x) ⫽ ln a ⫹ 2

3

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(⫺1 ⬍ x ⬍ ⫹1)

⫹

(x ⬍ ⫺1 or ⫹ 1 ⬍ x)

1 x⫺1 5 x⫹1

x 1 x ⫹ 2a ⫹ x 3 2a ⫹ x

3

⫹

5

⫹ ···

1 x 5 2a ⫹ x

(0 ⬍ x ⬍ ⬁) 5

册

⫹ ···

(0 ⬍ a ⬍ ⫹⬁, ⫺a ⬍ x ⬍ ⫹⬁) Series for the Trigonometric Functions. In the following formulas, all angles must be expressed in radians. If D ⫽ the number of degrees in the angle, and x ⫽ its radian measure, then x ⫽ 0.017453D. sin x ⫽ x ⫺

x3 x5 x7 ⫹ ⫺ ⫹ ··· 3! 5! 7!

cos x ⫽ 1 ⫺

x2 x4 x6 x8 ⫹ ⫺ ⫹ ⫺ ··· 2! 4! 6! 8!

tan x ⫽ x ⫹

x3 2x5 17x7 62x9 ⫹ ⫹ ⫹ ⫹ ··· 3 15 315 2835

cot x ⫽

(⫺⬁ ⬍ x ⬍ ⫹⬁) (⫺⬁ ⬍ x ⬍ ⫹⬁)

1 x x3 2x5 x7 ⫺ ⫺ ⫺ ⫺ ⫺ ··· x 3 45 945 4725

sin⫺1 y ⫽ y ⫹

y3 3y5 5y7 ⫹ ⫹ ⫹ ··· 6 40 112

tan⫺1 y ⫽ y ⫺

y3 y5 y7 ⫹ ⫺ ⫹ ··· 3 5 7

cos⫺1 y ⫽ 1⁄2␲ ⫺ sin⫺1 y

冉

⫺

␲ ␲ ⬍x⬍⫹ 2 2

冊

(⫺ ␲ ⬍ x ⬍ ⫹ ␲)

(⫺1 ⬉ y ⬉ ⫹1) (⫺1 ⬉ y ⬉ ⫹1)

cot⫺1 y ⫽ 1⁄2␲ ⫺ tan⫺1 y

Reversing a Series. If y ⫽ x ⫹ bx2 ⫹ cx3 ⫹ dx4 ⫹ ex5 ⫹ · · · , then x ⫽ y ⫺ by2 ⫹ (2b2 ⫺ c)y3 ⫺ (5b3 ⫺ 5bc ⫹ d)y4 ⫹ (14b4 ⫺ 21b2c ⫹ 6bd ⫹ 3c2 ⫺ e)y5 ⫹ · · · , provided the latter series is convergent. Fourier’s Series. Let f (x) be a function which is finite in the interval from x ⫽ ⫺c to x ⫽ ⫹c and whose graph has finite arc length in that interval.* Then, for any value of x between ⫺c and c, * If x ⫽ x0 is a point of discontinuity, f (x0) is to be defined as 1⁄2[f1(x0) ⫹ f2(x0)], where f1(x0) is the limit of f (x) when x approaches x0 from below, and f2(x0) is the limit of f(x) when x approaches x0 from above.

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f(x) ⫽ 1⁄2a0 ⫹ a1 cos

2.117

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␲x 2␲c 3␲x ⫹ a2 cos ⫹ a3 cos ⫹ ··· c c c ␲x 2␲x 3␲x ⫹ b2 sin ⫹ b3 sin ⫹ ··· c c c

⫹ b1 sin where the constant coefficients are determined as follows: an ⫽

1 c

冕

c

⫺c

f(t) cos

n␲t dt c

bn ⫽

1 c

冕

c

⫺c

f(t) sin

n␲t dt c

In case the curve y ⫽ f (x) is symmetrical with respect to the origin, the a’s are all zero, and the series is a sine series. In case the curve is symmetrical with respect to the y axis, the b’s are all zero, and a cosine series results. (In this case, the series will be valid not only for values of x between ⫺c and c, but also for x ⫽ ⫺c and x ⫽ c .) A Fourier series can always be integrated term by term; but the result of differentiating term by term may not be a convergent series.

TABLE 2.25 Some Constants Constant

Number

Log10 of Number

Pi (␲) Napierian Base (e) M ⫽ log10e 1 ⫼ M ⫽ loge 10 180 ⫼ ␲ ⫽ degrees in 1 radian ␲ ⫼ 180 ⫽ radians in 1⬚ ␲ ⫼ 10800 ⫽ radians in 1⬘ ␲ ⫼ 648000 ⫽ radians in 1⬙

3.14159 26535 89793 23846 2.71828 18284 59045 23536 0.43429 44819 03251 82765 2.30258 50929 94045 68402 57.2957 795 0.01745 329 0.00029 08882 0.00000 48481 36811 095

0.49714 98726 94133 85435 0.43429 448 9.63778 43113 00536 78912 ⫺ 10 0.36221 569 1.75812 263 8.24187 737 ⫺ 10 6.46372 612 ⫺ 10 4.68557 487 ⫺ 10

2.3 2.3.1

STATISTICS IN CHEMICAL ANALYSIS Introduction

Each observation in any branch of scientific investigation is inaccurate to some degree. Often the accurate value for the concentration of some particular constituent in the analyte cannot be determined. However, it is reasonable to assume the accurate value exists, and it is important to estimate the limits between which this value lies. It must be understood that the statistical approach is concerned with the appraisal of experimental design and data. Statistical techniques can neither detect nor evaluate constant errors (bias); the detection and elimination of inaccuracy are analytical problems. Nevertheless, statistical techniques can assist considerably in determining whether or not inaccuracies exist and in indicating when procedural modifications have reduced them. By proper design of experiments, guided by a statistical approach, the effects of experimental variables may be found more efficiently than by the traditional approach of holding all variables constant but one and systematically investigating each variable in turn. Trends in data may be sought to track down nonrandom sources of error.

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Errors in Quantitative Analysis

Two broad classes of errors may be recognized. The first class, determinate or systematic errors, is composed of errors that can be assigned to definite causes, even though the cause may not have been located. Such errors are characterized by being unidirectional. The magnitude may be constant from sample to sample, proportional to sample size, or variable in a more complex way. An example is the error caused by weighing a hygroscopic sample. This error is always positive in sign; it increases with sample size but varies depending on the time required for weighing, with humidity and temperature. An example of a negative systematic error is that caused by solubility losses of a precipitate. The second class, indeterminate or random errors, is brought about by the effects of uncontrolled variables. Truly random errors are as likely to cause high as low results, and a small random error is much more probable than a large one. By making the observation coarse enough, random errors would cease to exist. Every observation would give the same result, but the result would be less precise than the average of a number of finer observations with random scatter. The precision of a result is its reproducibility; the accuracy is its nearness to the truth. A systematic error causes a loss of accuracy, and it may or may not impair the precision depending upon whether the error is constant or variable. Random errors cause a lowering of reproducibility, but by making sufficient observations it is possible to overcome the scatter within limits so that the accuracy may not necessarily be affected. Statistical treatment can properly be applied only to random errors.

2.3.3

Representation of Sets of Data

Raw data are collected observations that have not been organized numerically. An average is a value that is typical or representative of a set of data. Several averages can be defined, the most common being the arithmetic mean (or briefly, the mean), the median, the mode, and the geometric mean. The mean of a set of N numbers, x1, x2, x3, . . . , xN, is denoted by x and is defined as: x⫽

x1 ⫹ x2 ⫹ x3 ⫹ · · · ⫹ xN N

(2.4)

It is an estimation of the unknown true value ␮ of an infinite population. We can also define the sample variance s2 as follows:

冘(x ⫺ x) s ⫽ N

2

i⫽1

i

2

N⫺1

(2.5)

The values of x and s2 vary from sample set to sample set. However, as N increases, they may be expected to become more and more stable. Their limiting values, for very large N, are numbers characteristic of the frequency distribution, and are referred to as the population mean and the population variance, respectively. The median of a set of numbers arranged in order of magnitude is the middle value or the arithmetic mean of the two middle values. The median allows inclusion of all data in a set without undue influence from outlying values; it is preferable to the mean for small sets of data. The mode of a set of numbers is that value which occurs with the greatest frequency (the most common value). The mode may not exist, and even if it does exist it may not be unique. The empirical relation that exists between the mean, the mode, and the median for unimodal frequency curves which are moderately asymmetrical is: Mean ⫺ mode ⫽ 3(mean ⫺ median)

(2.6)

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The geometric mean of a set of N numbers is the Nth root of the product of the numbers: N p x1x2x3 . . . xN

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(2.7)

The root mean square (RMS) or quadratic mean of a set of numbers is defined by: RMS ⫽ p x 2 ⫽ 2.3.4

q 冘 x /N N

i⫽1

2 i

(2.8)

The Normal Distribution of Measurements

The normal distribution of measurements (or the normal law of error) is the fundamental starting point for analysis of data. When a large number of measurements are made, the individual measurements are not all identical and equal to the accepted value ␮, which is the mean of an infinite population or universe of data, but are scattered about ␮, owing to random error. If the magnitude of any single measurement is the abscissa and the relative frequencies (i.e., the probability) of occurrence of different-sized measurements are the ordinate, the smooth curve drawn through the points (Fig. 2.10) is the normal or Gaussian distribution curve (also the error curve or probability curve). The term error curve arises when one considers the distribution of errors (x ⫺ ␮) about the true value.

FIGURE 2.10 The Normal Distribution Curve.

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The breadth or spread of the curve indicates the precision of the measurements and is determined by and related to the standard deviation, a relationship that is expressed in the equation for the normal curve (which is continuous and infinite in extent): Y⫽

1

␴ p 2␲

exp

冋 冉 冊册 ⫺

1 2

x⫺␮ ␴

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2

(2.9)

where ␴ is the standard deviation of the infinite population. The population mean ␮ expresses the magnitude of the quantity being measured. In a sense, ␴ measures the width of the distribution, and thereby also expresses the scatter or dispersion of replicate analytical results. When (x ⫺ ␮)/␴ is replaced by the standardized variable z, then: Y⫽

1

p 2␲

2

e⫺(1/2)z

(2.10)

The standardized variable (the z statistic) requires only the probability level to be specified. It measures the deviation from the population mean in units of standard deviation. Y is 0.399 for the most probable value, ␮. In the absence of any other information, the normal distribution is assumed to apply whenever repetitive measurements are made on a sample, or a similar measurement is made on different samples. Table 2.26a lists the height of an ordinate (Y) as a distance z from the mean, and Table 2.26b the area under the normal curve at a distance z from the mean, expressed as fractions of the total area, 1.000. Returning to Fig. 2.10, we note that 68.27% of the area of the normal distribution curve lies within 1 standard deviation of the center or mean value. Therefore, 31.73% lies outside those limits and 15.86% on each side. Ninety-five percent (actually 95.43%) of the area lies within 2 standard deviations, and 99.73% lies within 3 standard deviations of the mean. Often the last two areas are stated slightly different; viz. 95% of the area lies within 1.96␴ (approximately 2␴) and 99% lies within approximately 2.5␴. The mean falls at exactly the 50% point for symmetric normal distributions. Example 5 The true value of a quantity is 30.00, and ␴ for the method of measurement is 0.30. What is the probability that a single measurement will have a deviation from the mean greater than 0.45; that is, what percentage of results will fall outside the range 30.00 ⫾ 0.45? z⫽

x ⫺ ␮ 0.45 ⫽ ⫽ 1.5 ␴ 0.30

From Table 2.26b the area under the normal curve from ⫺1.5␴ to ⫹1.5␴ is 0.866, meaning that 86.6% of the measurements will fall within the range 30.00 ⫾ 0.45 and 13.4% will lie outside this range. Half of these measurements, 6.7%, will be less than 29.55; and a similar percentage will exceed 30.45. In actuality the uncertainty in z is about 1 in 15; therefore, the value of z could lie between 1.4 and 1.6; the corresponding areas under the curve could lie between 84% and 89%. Example 6 If the mean value of 500 determinations is 151 and ␴ ⫽ 15, how many results lie between 120 and 155 (actually any value between 119.5 and 155.5)? z⫽

119.5 ⫺ 151 ⫽ ⫺2.10 15

z⫽

155.5 ⫺ 151 ⫽ 0.30 15

Area: 0.482 0.118 Total area: 0.600

500(0.600) ⫽ 300 results

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TABLE 2.26a

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Ordinates (Y) of the Normal Distribution Curve at Values of z

z

0

1

2

3

4

5

6

7

8

9

0.0 0.1 0.2 0.3 0.4

0.3989 0.3970 0.3910 0.3814 0.3683

0.3989 0.3965 0.3902 0.3802 0.3668

0.3989 0.3961 0.3894 0.3790 0.3653

0.3988 0.3956 0.3885 0.3778 0.3637

0.3986 0.3951 0.3876 0.3765 0.3621

0.3984 0.3945 0.3867 0.3752 0.3605

0.3982 0.3939 0.3857 0.3739 0.3589

0.3980 0.3932 0.3847 0.3725 0.3572

0.3977 0.3925 0.3836 0.3712 0.3555

0.3973 0.3918 0.3825 0.3697 0.3538

0.5 0.6 0.7 0.8 0.9

0.3521 0.3332 0.3123 0.2897 0.2661

0.3503 0.3312 0.3101 0.2874 0.2637

0.3485 0.3292 0.3079 0.2850 0.2613

0.3467 0.3271 0.3056 0.2827 0.2589

0.3448 0.3251 0.3034 0.2803 0.2565

0.3429 0.3230 0.3011 0.2780 0.2541

0.3410 0.3209 0.2989 0.2756 0.2516

0.3391 0.3187 0.2966 0.2732 0.2492

0.3372 0.3166 0.2943 0.2709 0.2468

0.3352 0.3144 0.2920 0.2685 0.2444

1.0 1.1 1.2 1.3 1.4

0.2420 0.2179 0.1942 0.1714 0.1497

0.2396 0.2155 0.1919 0.1691 0.1476

0.2371 0.2131 0.1895 0.1669 0.1456

0.2347 0.2107 0.1872 0.1647 0.1435

0.2323 0.2083 0.1849 0.1626 0.1415

0.2299 0.2059 0.1826 0.1604 0.1394

0.2275 0.2036 0.1804 0.1582 0.1374

0.2251 0.2012 0.1781 0.1561 0.1354

0.2227 0.1989 0.1758 0.1539 0.1334

0.2203 0.1965 0.1736 0.1518 0.1315

1.5 1.6 1.7 1.8 1.9

0.1295 0.1109 0.0940 0.0790 0.0656

0.1276 0.1092 0.0925 0.0775 0.0644

0.1257 0.1074 0.0909 0.0761 0.0632

0.1238 0.1057 0.0893 0.0748 0.0620

0.1219 0.1040 0.0878 0.0734 0.0608

0.1200 0.1023 0.0863 0.0721 0.0596

0.1182 0.1006 0.0848 0.0707 0.0584

0.1163 0.0989 0.0833 0.0694 0.0573

0.1145 0.0973 0.0818 0.0681 0.0562

0.1127 0.0957 0.0804 0.0669 0.0551

2.0 2.1 2.2 2.3 2.4

0.0540 0.0440 0.0355 0.0283 0.0224

0.0529 0.0431 0.0347 0.0277 0.0219

0.0519 0.0422 0.0339 0.0270 0.0213

0.0508 0.0413 0.0332 0.0264 0.0208

0.0498 0.0404 0.0325 0.0258 0.0203

0.0488 0.0396 0.0317 0.0252 0.0198

0.0478 0.0387 0.0310 0.0246 0.0194

0.0468 0.0379 0.0303 0.0241 0.0189

0.0459 0.0371 0.0297 0.0235 0.0184

0.0449 0.0363 0.0290 0.0229 0.0180

2.5 2.6 2.7 2.8 2.9

0.0175 0.0136 0.0104 0.0079 0.0060

0.0171 0.0132 0.0101 0.0077 0.0058

0.0167 0.0129 0.0099 0.0075 0.0056

0.0163 0.0126 0.0096 0.0073 0.0055

0.0158 0.0122 0.0093 0.0071 0.0053

0.0154 0.0119 0.0091 0.0069 0.0051

0.0151 0.0116 0.0088 0.0067 0.0050

0.0147 0.0113 0.0086 0.0065 0.0048

0.0143 0.0110 0.0084 0.0063 0.0047

0.0139 0.0107 0.0081 0.0061 0.0046

3.0 3.1 3.2 3.3 3.4

0.0044 0.0033 0.0024 0.0017 0.0012

0.0043 0.0032 0.0023 0.0017 0.0012

0.0042 0.0031 0.0022 0.0016 0.0012

0.0040 0.0030 0.0022 0.0016 0.0011

0.0039 0.0029 0.0021 0.0015 0.0011

0.0038 0.0028 0.0020 0.0015 0.0010

0.0037 0.0027 0.0020 0.0014 0.0010

0.0036 0.0026 0.0019 0.0014 0.0010

0.0035 0.0025 0.0018 0.0013 0.0009

0.0034 0.0025 0.0018 0.0013 0.0009

3.5 3.6 3.7 3.8 3.9

0.0009 0.0006 0.0004 0.0003 0.0002

0.0008 0.0006 0.0004 0.0003 0.0002

0.0008 0.0006 0.0004 0.0003 0.0002

0.0008 0.0005 0.0004 0.0003 0.0002

0.0008 0.0005 0.0004 0.0003 0.0002

0.0007 0.0005 0.0004 0.0002 0.0002

0.0007 0.0005 0.0003 0.0002 0.0002

0.0007 0.0005 0.0003 0.0002 0.0002

0.0007 0.0005 0.0003 0.0002 0.0001

0.0006 0.0004 0.0003 0.0002 0.0001

2.3.5

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Standard Deviation as a Measure of Dispersion

Several ways may be used to characterize the spread or dispersion in the original data. The range is the difference between the largest value and the smallest value in a set of observations. However, almost always the most efficient quantity for characterizing variability is the standard deviation (also called the root mean square).

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TABLE 2.26b Areas Under the Normal Distribution Curve from 0 to z z

0

1

2

3

4

5

6

7

8

9

0.0 0.1 0.2 0.3 0.4

0.0000 0.0398 0.0793 0.1179 0.1554

0.0040 0.0438 0.0832 0.1217 0.1591

0.0080 0.0478 0.0871 0.1255 0.1628

0.0120 0.0517 0.0910 0.1293 0.1664

0.0160 0.0557 0.0948 0.1331 0.1700

0.0199 0.0596 0.0987 0.1368 0.1736

0.0239 0.0636 0.1026 0.1406 0.1772

0.0279 0.0675 0.1064 0.1443 0.1808

0.0319 0.0714 0.1103 0.1480 0.1844

0.0359 0.0754 0.1141 0.1517 0.1879

0.5 0.6 0.7 0.8 0.9

0.1915 0.2258 0.2580 0.2881 0.3159

0.1950 0.2291 0.2612 0.2910 0.3186

0.1985 0.2324 0.2642 0.2939 0.3212

0.2019 0.2357 0.2673 0.2967 0.3238

0.2054 0.2389 0.2704 0.2996 0.3264

0.2088 0.2422 0.2734 0.3023 0.3289

0.2123 0.2454 0.2764 0.3051 0.3315

0.2157 0.2486 0.2794 0.3078 0.3340

0.2190 0.2518 0.2823 0.3106 0.3365

0.2224 0.2549 0.2852 0.3133 0.3389

1.0 1.1 1.2 1.3 1.4

0.3413 0.3643 0.3849 0.4032 0.4192

0.3438 0.3665 0.3869 0.4049 0.4207

0.3461 0.3686 0.3888 0.4066 0.4222

0.3485 0.3708 0.3907 0.4082 0.4236

0.3508 0.3729 0.3925 0.4099 0.4251

0.3531 0.3749 0.3944 0.4115 0.4265

0.3554 0.3770 0.3962 0.4131 0.4279

0.3577 0.3790 0.3980 0.4147 0.4292

0.3599 0.3810 0.3997 0.4162 0.4306

0.3621 0.3830 0.4015 0.4177 0.4319

1.5 1.6 1.7 1.8 1.9

0.4332 0.4452 0.4554 0.4641 0.4713

0.4345 0.4463 0.4564 0.4649 0.4719

0.4357 0.4474 0.4573 0.4656 0.4726

0.4370 0.4484 0.4582 0.4664 0.4732

0.4382 0.4495 0.4591 0.4671 0.4738

0.4394 0.4505 0.4599 0.4678 0.4744

0.4406 0.4515 0.4608 0.4686 0.4750

0.4418 0.4525 0.4616 0.4693 0.4756

0.4429 0.4535 0.4625 0.4699 0.4761

0.4441 0.4545 0.4633 0.4706 0.4767

2.0 2.1 2.2 2.3 2.4

0.4772 0.4821 0.4861 0.4893 0.4918

0.4778 0.4826 0.4864 0.4896 0.4920

0.4783 0.4830 0.4868 0.4898 0.4922

0.4788 0.4834 0.4871 0.4901 0.4925

0.4793 0.4838 0.4875 0.4904 0.4927

0.4798 0.4842 0.4878 0.4906 0.4929

0.4803 0.4846 0.4881 0.4909 0.4931

0.4808 0.4850 0.4884 0.4911 0.4932

0.4812 0.4854 0.4887 0.4913 0.4934

0.4817 0.4857 0.4890 0.4916 0.4936

2.5 2.6 2.7 2.8 2.9

0.4938 0.4953 0.4965 0.4974 0.4981

0.4940 0.4955 0.4966 0.4975 0.4982

0.4941 0.4956 0.4967 0.4976 0.4982

0.4943 0.4957 0.4968 0.4977 0.4983

0.4945 0.4959 0.4969 0.4977 0.4984

0.4946 0.4960 0.4970 0.4978 0.4984

0.4948 0.4961 0.4971 0.4979 0.4985

0.4949 0.4962 0.4972 0.4979 0.4985

0.4951 0.4963 0.4973 0.4980 0.4986

0.4952 0.4964 0.4974 0.4981 0.4986

3.0 3.1 3.2 3.3 3.4

0.4987 0.4990 0.4993 0.4995 0.4997

0.4987 0.4991 0.4993 0.4995 0.4997

0.4987 0.4991 0.4994 0.4995 0.4997

0.4988 0.4991 0.4994 0.4996 0.4997

0.4988 0.4992 0.4994 0.4996 0.4997

0.4989 0.4992 0.4994 0.4996 0.4997

0.4989 0.4992 0.4994 0.4996 0.4997

0.4989 0.4992 0.4995 0.4996 0.4997

0.4990 0.4993 0.4995 0.4996 0.4997

0.4990 0.4993 0.4995 0.4997 0.4998

3.5 3.6 3.7 3.8 3.9

0.4998 0.4998 0.4999 0.4999 0.5000

0.4998 0.4998 0.4999 0.4999 0.5000

0.4998 0.4999 0.4999 0.4999 0.5000

0.4998 0.4999 0.4999 0.4999 0.5000

0.4998 0.4999 0.4999 0.4999 0.5000

0.4998 0.4999 0.4999 0.4999 0.5000

0.4998 0.4999 0.4999 0.4999 0.5000

0.4998 0.4999 0.4999 0.4999 0.5000

0.4998 0.4999 0.4999 0.4999 0.5000

0.4998 0.4999 0.4999 0.4999 0.5000

The standard deviation is the square root of the average squared differences between the individual observations and the population mean:

冘 (x ⫺ ␮) N

␴⫽

q

i⫽1

i

N

2

(2.11)

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The standard deviation ␴ may be estimated by calculating the standard deviation s drawn from a small sample set as follows:

冘 (x ⫺ x)

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N

s⫽

q

i⫽1

i

2

s⫽

or

N

q

x 21 ⫹ x 22 ⫹ · · · ⫺ [(x1 ⫹ x2 ⫹ · · ·)2]/N N⫺1

(2.12)

where xi ⫺ x represents the deviation of each number in the array from the arithmetic mean. Since two pieces of information, namely s and x, have been extracted from the data, we are left with N ⫺ 1 degrees of freedom (df); that is, independent data points available for measurement of precision. If a relatively large sample of data corresponding to N ⬎ 30 is available, its mean can be taken as a measure of ␮, and s as equal to ␴. So basic is the notion of a statistical estimate of a physical parameter that statisticians use Greek letters for the parameters and Latin letters for the estimates. For many purposes, one uses the variance, which for the sample is s2 and for the entire populations is ␴ 2. The variance s2 of a finite sample is an unbiased estimate of ␴ 2, whereas the standard deviation s is not an unbiased estimate of ␴. Because the standard deviation ␴ for the universe is a characteristic of the measuring procedure, it is possible to get a good estimate not only from a long series of repeated analyses of the same sample, but also by taking together several short series measured with slightly different samples of the same type. When a series of observations can be logically arranged into k subgroups, the variance is calculated by summing the squares of the deviations for each subgroup, and then adding all the k sums and dividing by N ⫺ k because one degree of freedom is lost in each subgroup. It is not required that the number of repeated analyses in the different groups be the same. For two groups of observations consisting of NA and NB members of standard deviations sA and sB, respectively, the variance is given by: s2 ⫽

(NA ⫺ 1)sA2 ⫹ (NB ⫺ 1)sB2 NA ⫹ NB ⫺ 2

(2.13)

Another measure of dispersion is the coefficient of variation, which is merely the standard deviation expressed as a fraction of the arithmetic mean, viz., s/x . It is useful mainly to show whether the relative or the absolute spread of values is constant as the values are changed. 2.3.6

Student’s Distribution or t Test

In the next several sections, the theoretical distributions and tests of significance will be examined beginning with Student’s distribution or t test. If the data contained only random (or chance) errors, the cumulative estimates x and s would gradually approach the limits ␮ and ␴. The distribution of results would be normally distributed with mean ␮ and standard deviation ␴. Were the true mean of the infinite population known, it would also have some symmetrical type of distribution centered around ␮. However, it would be expected that the dispersion or spread of this dispersion about the mean would depend on the sample size. The standard deviation of the distribution of means equals ␴/N1/2. Since ␴ is not usually known, its approximation for a finite number of measurements is overcome by the Student t test. It is a measure of error between ␮ and x. The Student t takes into account both the possible variation of the value of x from ␮ on the basis of the expected variance ␴ 2/N1/2 and the reliability of using s in place of ␴. The distribution of the statistic is: ⫾t ⫽

x⫺␮ s/p N

or

␮⫽x⫾

ts pN

(2.14)

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The distribution of the t-statistic (x ⫺ ␮)s is symmetrical about zero and is a function of the degrees of freedom. Limits assigned to the distance on either side of ␮ are called confidence limits. The percentage probability that ␮ lies within this interval is called the confidence level. The level of significance or error probability (100 ⫺ confidence level or 100 ⫺ ␣) is the percent probability that ␮ will lie outside the confidence interval, and represents the chances of being incorrect in stating that ␮ lies within the confidence interval. Values of t are in Table 2.27 for any desired degrees of freedom and various confidence levels. An analytical procedure is often tested on materials of known composition. These materials may be pure substances, standard samples, or materials analyzed by some other more accurate method. Repeated determinations on a known material furnish data for both an estimate of the precision and a test for the presence of a constant error in the results. The standard deviation is found from Equation 12 (with the known composition replacing ␮). A calculated value for t (Eq. 14) in excess of the appropriate value in Table 2.27 is interpreted as evidence of the presence of a constant error at the indicated level of significance.

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TABLE 2.27 Percentile Values for Student t Distribution df

t 0.995

t 0.99

t 0.975

t 0.95

t 0.90

t 0.80

t 0.75

t 0.70

t 0.60

t 0.55

1 2 3 4

63.66 9.92 5.84 4.60

31.82 6.96 4.54 3.75

12.71 4.30 3.18 2.78

6.31 2.92 2.35 2.13

3.08 1.89 1.64 1.53

1.376 1.061 0.978 0.941

1.000 0.816 0.765 0.741

0.727 0.617 0.584 0.569

0.325 0.289 0.277 0.271

0.158 0.142 0.137 0.134

5 6 7 8 9

4.03 3.71 3.50 3.36 3.25

3.36 3.14 3.00 2.90 2.82

2.57 2.45 2.36 2.31 2.26

2.02 1.94 1.90 1.86 1.83

1.48 1.44 1.42 1.40 1.38

0.920 0.906 0.896 0.889 0.883

0.727 0.718 0.711 0.706 0.703

0.559 0.553 0.549 0.546 0.543

0.267 0.265 0.263 0.262 0.261

0.132 0.131 0.130 0.130 0.129

10 11 12 13 14

3.17 3.11 3.06 3.01 2.98

2.76 2.72 2.68 2.65 2.62

2.23 2.20 2.18 2.16 2.14

1.81 1.80 1.78 1.77 1.76

1.37 1.36 1.36 1.35 1.34

0.879 0.876 0.873 0.870 0.868

0.700 0.697 0.695 0.694 0.692

0.542 0.540 0.539 0.538 0.537

0.260 0.260 0.259 0.259 0.258

0.129 0.129 0.128 0.128 0.128

15 16 17 18 19

2.95 2.92 2.90 2.88 2.86

2.60 2.58 2.57 2.55 2.54

2.13 2.12 2.11 2.10 2.09

1.75 1.75 1.74 1.73 1.73

1.34 1.34 1.33 1.33 1.33

0.866 0.865 0.863 0.862 0.861

0.691 0.690 0.689 0.688 0.688

0.536 0.535 0.534 0.534 0.533

0.258 0.258 0.257 0.257 0.257

0.128 0.128 0.128 0.127 0.127

20 21 22 23 24

2.84 2.83 2.82 2.81 2.80

2.53 2.52 2.51 2.50 2.49

2.09 2.08 2.07 2.07 2.06

1.72 1.72 1.72 1.71 1.71

1.32 1.32 1.32 1.32 1.32

0.860 0.859 0.858 0.858 0.857

0.687 0.686 0.686 0.685 0.685

0.533 0.532 0.532 0.532 0.531

0.257 0.257 0.256 0.256 0.256

0.127 0.127 0.127 0.127 0.127

25 26 27 28 29

2.79 2.78 2.77 2.76 2.76

2.48 2.48 2.47 2.47 2.46

2.06 2.06 2.05 2.05 2.04

1.71 1.71 1.70 1.70 1.70

1.32 1.32 1.31 1.31 1.31

0.856 0.856 0.855 0.855 0.854

0.684 0.684 0.684 0.683 0.683

0.531 0.531 0.531 0.530 0.530

0.256 0.256 0.256 0.256 0.256

0.127 0.127 0.127 0.127 0.127

30 40 60 120 ⬁

2.75 2.70 2.66 2.62 2.58

2.46 2.42 2.39 2.36 2.33

2.04 2.02 2.00 2.98 1.96

1.70 1.68 1.67 1.66 1.645

1.31 1.30 1.30 1.29 1.28

0.854 0.851 0.848 0.845 0.842

0.683 0.681 0.679 0.677 0.674

0.530 0.529 0.527 0.526 0.524

0.256 0.255 0.254 0.254 0.253

0.127 0.126 0.126 0.126 0.126

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Example 7 A new method for the analysis of iron using pure FeO was replicated with five samples giving these results (in % Fe): 76.95, 77.02, 76.90, 77.20, and 77.50. Does a systematic error exist? From Equation 4, x is 77.11; and from Equation 5, s is 0.24 for 4 degrees of freedom. Because ␴ is not known, the Student t0.975 (2.78 for 4 degrees of freedom) is used to calculate the confidence interval at the 95% probability level.

␮⫽x⫾

ts pN

⫽ 77.11 ⫾

(2.78) (0.24) p5

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⫽ 77.11 ⫾ 0.30

We used a two-tailed test. Upon rereading the problem, we realize that this was pure FeO whose iron content was 77.60% so that ␮ ⫽ 77.60 and the confidence interval does not include the known value. Since the FeO was a standard, a one-tailed test should have been used since only random values would be expected to exceed 77.60%. Now the Student t value of 2.13 (for ⫺t0.05) should have been used, and now the confidence interval becomes 77.11 ⫾ 0.23. A systematic error is presumed to exist. The t test can be applied to differences between pairs of observations. Perhaps only a single pair can be performed at one time, or possibly one wishes to compare two methods using samples of differing analytical content. It is still necessary that the two methods possess the same inherent standard deviation. An average difference d calculated, and individual deviations from d are used to evaluate the variance of the differences. Example 8 From the following data do the two methods actually give concordant results?

Sample

Method A

Method B

1 2 3 4

33.27 51.34 23.91 47.04

33.04 50.96 23.77 46.79

Difference d1 d2 d3 d4

⫽ 0.23 ⫽ 0.38 ⫽ 0.14 ⫽ 0.25

d ⫽ 0.25

sd ⫽ t⫽

p

冘 (d ⫺ d) ⫽ 0.099 2

N⫺1

0.25 4 ⫺ 1 ⫽ 4.30 0.099 p

From Table 2.27, t0.975 ⫽ 3.18 (at 95% probability) and t0.995 ⫽ 5.84 (at 99% probability). The difference between the two methods is probably significant. If the t-value falls short of the formal significance level, this is not to be interpreted as proving the absence of a systematic error. Perhaps the data were insufficient in precision or in number to establish the presence of a constant error. Especially when the calculated value for t is only slightly short of the tabulated value, some additional data may suffice to build up the evidence for a constant error (or the lack thereof).

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Should there be more than one known material, a weighted average of the individual differences (x) should be taken. The value of s should be based on the combined estimate from the two or more materials (perhaps different primary standards for bases). Should the materials differ markedly in composition, a plot of the individual constant errors against composition should be made. If the constant error appear to depend upon the composition, they should not be pooled in a weighted average. The t test is also used to judge whether a given lot of material conforms to a particular specification. If both plus and minus departures from the known value are to be guarded against, a twotailed test is involved. If departures in only one direction are undesirable, then the 10% level values for t are appropriate for the 5% level in one direction. Similarly, the 2% level should be used to obtain the 1% level to test the departure from the known value in one direction only; these constitute a one-tailed test. More on this subject will be in the next section. Sometimes just one determination is available on each of several known materials similar in composition. A single determination by each of two procedures (or two analysts) on a series of material may be used to test for a relative bias between the two methods, as in Example 2.4. Of course, the average difference does not throw any light on which procedure has the larger constant error. It only supplies a test as to whether the two procedures are in disagreement.

2.3.7

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Hypotheses About Means

Statistical methods are frequently used to give a “yes” or “no” answer to a particular question concerning the significance of data. When performing hypothesis tests on real data, we cannot set an absolute cutoff as to where we can expect to find no values from the population against which we are testing data, but we can set a limit beyond which we consider it very unlikely to find a member of the population. If a measurement is made that does in fact fall outside the specified range, the probability of its happening by chance alone can be rejected; something beyond the randomness of the reference population must be operating. In other words, hypothesis testing is an attempt to determine whether a given measured statistic could have come from some hypothesized population. In attempting to reach decisions, it is useful to make assumptions or guesses about the populations involved. Such assumptions, which may or may not be true, are called statistical hypotheses and in general are statements about the probability distributions of the populations. A common procedure is to set up a null hypothesis, denoted by H0, which states that there is no significant difference between two sets of data or that a variable exerts no significant effect. Any hypothesis which differs from a null hypothesis is called an alternative hypothesis, denoted by H1. Our answer is qualified by a confidence level (or level of significance) indicating the degree of certainty of the answer. Generally confidence levels of 95% and 99% are chosen to express the probability that the answer is correct. These are also denoted as the 0.05 and 0.01 level of significance, respectively. When the hypothesis can be rejected at the 0.05 level of significance, but not at the 0.01 level, we can say that the sample results are probably significant. If, however, the hypothesis is also rejected at the 0.01 level, the results become highly significant. The abbreviated table on the next page, which gives critical values of z for both one-tailed and two-tailed tests at various levels of significance, will be found useful for purposes of reference. Critical values of z for other levels of significance are found by the use of Table 2.26b. For a small number of samples we replace z, obtained from above or from Table 2.26b, by t from Table 2.27, and we replace ␴ by: [ p N/(N ⫺ 1)] s

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Level of significance, ␣

0.10 ⫺1.28 1.28

Critical values of z for one-tailed tests

or

Critical values of z for two-tailed tests

⫺1.645 and 1.645

0.05

or

⫺1.645 1.645

⫺1.96 and 1.96

0.01

or

⫺2.33 2.33

⫺2.58 and 2.58

0.005

or

⫺2.58 2.58

⫺2.81 and 2.81

0.002

or

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⫺2.88 2.88

⫺3.08 and 3.08

Procedures which enable us to decide whether to accept or reject hypotheses or to determine whether observed samples differ significantly from expected results are called tests of hypotheses, tests of significance, or rules of decision. For example, a set of z values outside the range ⫺1.96 to 1.96 (at the 0.05 level of significance for a two-tailed test), constitute what is called the critical region or region of rejection of the hypothesis. The set of z results inside the range ⫺1.96 to 1.96 could then be called the region of acceptance of the hypothesis. Example 9 In the past a method gave ␮ ⫽ 0.050%. A recent set of 10 results gave x ⫽ 0.053% and s ⫽ 0.003%. Is everything satisfactory at a level of significance of 0.05? Of 0.01? We wish to decide between the hypotheses: H0: ␮ ⫽ 0.050%

and the method is working properly, and

H1: ␮ ⫽ 0.050%

and the method is not working properly.

A two-tailed test is required; that is, both tails on the distribution curve are involved: t⫽

0.053 ⫺ 0.050 p 10 ⫺ 1 ⫽ ⫺3.00 0.003

Enter Table 2.27 for nine degrees of freedom under the column headed t0.975 for the 0.05 level of significance, and the column t0.995 for the 0.01 level of significance. At the 0.05 level, accept H0 if t lies inside the interval ⫺t0.975 to t0.975, that is, within ⫺2.26 and 2.26; reject otherwise. Since t ⫽ ⫺3.00, we reject H0. At the 0.01 level of significance, the corresponding interval is ⫺3.25 to 3.25, which t lies within, indicating acceptance of H0. Because we can reject H0 at the 0.05 level but not at the 0.01 level of significance, we can say that the sample results are probably significant and that the method is working properly. Let us digress a moment and consider when a two-tailed test is needed, and what a one-tailed test implies. We “assume” that the measurements can be described by the curve shown in Fig. 2.10. If so, then 95% of the time a sample from the specified population will fall within the indicated range and 5% of the time it will fall outside; 2.5% of the time it is outside on the high side of the range, and 2.5% of the time it is below the low side of the range. Our assumption implies that if ␮ does not equal the hypothesized value, the probability of its being above the hypothesized value is equal to the probability of its being below the hypothesized value. There will be incidences when the foregoing assumptions for a two-tailed test will not be true. Perhaps some physical situation prevents ␮ from ever being less than the hypothesized value; it can only be equal or greater. No results would ever fall below the low end of the confidence interval; only the upper end of the distribution is operative. Now random samples will exceed the upper bound only 2.5% of the time, not the 5% specified in two-tail testing. Thus, where the possible values are restricted, what was supposed to be a hypothesis test at the 95% confidence level is actually being performed at a 97.5% confidence level. Stated in another way, 95% of the population data lie within the interval below ␮ ⫹ 1.65␴ and 5% lie above. Of course, the opposite situation might also occur and only the lower end of the distribution is operative.

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Example 10 Six samples from a bulk chemical shipment averaged 77.50% active ingredient with s ⫽ 1.45%. The manufacturer claimed 80.00%. Can this claim be supported? A one-tailed test is required since the alternative hypothesis states that the population parameter is equal to or less than the hypothesized value. t⫽

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77.50 ⫺ 80.00 p 6 ⫺ 1 ⫽ 3.86 1.45

Since t0.95 ⫽ ⫺2.01, and t0.99 ⫽ ⫺3.36, the hypothesis is rejected at both the 0.05 and the 0.01 levels of significance. It is extremely unlikely that the claim is justified.

2.3.8

The Chi-square (␹ 2 ) Distribution

The ␹2 distribution describes the behavior of variances. Actually there is not a single ␹2 distribution but a whole set of distributions. Each distribution depends upon the number of degrees of freedom (designated variously as df, d.f., or f ) in that distribution. Table 2.28 is laid out so that the horizontal axis is labeled with probability levels, while the vertical axis is listed in descending order of increasing number of degrees of freedom. The entries increase both as you read down and across the table. Although Table 2.28 does not display the values for the mid-range of the distributions, at the 50% point of each distribution, the expected value of ␹2 is equal to the degrees of freedom. Estimates of the variance are uncertain when based only on a few degrees of freedom. With the 10 samples in Example 11, the standard deviation can vary by a large factor purely by random chance alone. Even 31 samples gives a spread of standard deviation of 2.6 at the 95% confidence level. Understanding the ␹2 distribution allows us to calculate the expected values of random variables that are normally and independently distributed. In least squares multiple regression, or in calibration work in general, there is a basic assumption that the error in the response variable is random and normally distributed, with a variance that follows a ␹2 distribution. Confidence limits for an estimate of the variance may be calculated as follows. For each group of samples a standard deviation is calculated. These estimates of ␴ possess a distribution called the ␹2 distribution:

␹2 ⫽

s2 ␴ /df 2

(2.15)

The upper and lower confidence limits for the standard deviation are obtained by dividing (N ⫺ 1)s2 by two entries taken from Table 2.28. The estimate of variance at the 90% confidence limits is for use in the entries ␹ 20.05 and ␹ 20.95 (for 5% and 95%) with N degrees of freedom. Example 11 The variance obtained for 10 samples is (0.65)2. ␴ 2 is known to be (0.75)2. How reliable is s2 as an estimate of ␴ 2 ? s2 (N ⫺ 1) s2 (N ⫺ 1) ⬍ ␴2 ⬍ 2 2 ␹ 0.975 ␹ 0.025 (0.65)2 (10 ⫺ 1) (0.65)2 (10 ⫺ 1) ⬍ ␴2 ⬍ 19.02 2.70 0.20 ⬍ ␴ 2 ⬍ 1.43 Thus, only one time in 40 will 9s2/␴ 2 be less than 2.70 by chance alone. Similarly, only one time

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TABLE 2.28 Percentile Values for the Chi-square (␹ 2) Distribution ␹ 20.995

␹ 20.99

2 ␹ 0.975

1 2 3 4

7.88 10.6 12.8 14.9

6.63 9.21 11.3 13.3

5.02 7.38 9.35 11.1

5 6 7 8 9

16.7 18.5 20.3 22.0 23.6

15.1 16.8 18.5 20.1 21.7

12.8 14.4 16.0 17.5 19.0

10 11 12 13 14

25.2 26.8 28.3 29.8 31.3

23.2 24.7 26.2 27.7 29.1

15 16 17 18 19

32.8 34.3 35.7 37.2 38.6

20 21 22 23 24

df

␹ 20.95 3.84 5.99 7.81 9.49

2 ␹ 0.90

2 ␹ 0.75

2 ␹ 0.50

2 ␹ 0.25

2 ␹ 0.10

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␹ 20.05

2 ␹ 0.025

2 ␹ 0.01

2 ␹ 0.005

2.71 4.61 6.25 7.78

1.32 2.77 4.11 5.39

0.455 1.39 2.37 3.36

0.102 0.575 1.21 1.92

0.0158 0.211 0.584 1.06

0.0039 0.103 0.352 0.711

0.0010 0.0506 0.216 0.484

0.0002 0.0201 0.115 0.297

0.0000 0.0100 0.072 0.207

11.1 12.6 14.1 15.5 16.9

9.24 10.6 12.0 13.4 14.7

6.63 7.84 9.04 10.2 11.4

4.35 5.35 6.35 7.34 8.34

2.67 3.45 4.25 5.07 5.90

1.61 2.20 2.83 3.49 4.17

1.15 1.64 2.17 2.73 3.33

0.831 1.24 1.69 2.18 2.70

0.554 0.872 1.24 1.65 2.09

0.412 0.676 0.989 1.34 1.73

20.5 21.9 23.3 24.7 26.1

18.3 19.7 21.0 22.4 23.7

16.0 17.3 18.5 19.8 21.1

12.5 13.7 14.8 16.0 17.1

9.34 10.3 11.3 12.3 13.3

6.74 7.58 8.44 9.30 10.2

4.87 5.58 6.30 7.04 7.79

3.94 4.57 5.23 5.89 6.57

3.25 3.82 4.40 5.01 5.63

2.56 3.05 3.57 4.11 4.66

2.16 2.60 3.07 3.57 4.07

30.6 32.0 33.4 34.8 36.2

27.5 28.8 30.2 31.5 32.9

25.0 26.3 27.6 28.9 30.1

22.3 23.5 24.8 26.0 27.2

18.2 19.4 20.5 21.6 22.7

14.3 15.3 16.3 17.3 18.3

11.0 11.9 12.8 13.7 14.6

8.55 9.31 10.1 10.9 11.7

7.26 7.96 8.67 9.39 10.1

6.26 6.91 7.56 8.23 8.91

5.23 5.81 6.41 7.01 7.63

4.60 5.14 5.70 6.26 6.84

40.0 41.4 42.8 44.2 45.6

37.6 38.9 40.3 41.6 43.0

34.2 35.5 36.8 38.1 39.4

31.4 32.7 33.9 35.2 36.4

28.4 29.6 30.8 32.0 33.2

23.8 24.9 26.0 27.1 28.2

19.3 20.3 21.3 22.3 23.3

15.5 16.3 17.2 18.1 19.0

12.4 13.2 14.0 14.8 15.7

10.9 11.6 12.3 13.1 13.8

9.59 10.3 11.0 11.7 12.4

8.26 8.90 9.54 10.2 10.9

7.43 8.03 8.64 9.26 9.89

25 26 27 28 29

46.9 48.3 49.6 51.0 52.3

44.3 45.6 47.0 48.3 49.6

40.6 41.9 43.2 44.5 45.7

37.7 38.9 40.1 41.3 42.6

34.4 35.6 36.7 37.9 39.1

29.3 30.4 31.5 32.6 33.7

24.3 25.3 26.3 27.3 28.3

19.9 20.8 21.7 22.7 23.6

16.5 17.3 18.1 18.9 19.8

14.6 15.4 16.2 16.9 17.7

13.1 13.8 14.6 15.39 16.0

11.5 12.2 12.9 13.6 14.3

10.5 11.2 11.8 12.5 13.1

30 40 50 60

53.7 66.8 79.5 92.0

50.9 63.7 76.2 88.4

47.0 59.3 71.4 83.3

43.8 55.8 67.5 79.1

40.3 51.8 63.2 74.4

34.8 45.6 56.3 67.0

29.3 39.3 49.3 59.3

24.5 33.7 42.9 52.3

20.6 29.1 37.7 46.5

18.5 26.5 34.8 43.2

16.8 24.4 32.4 40.5

15.0 22.2 29.7 37.5

13.8 20.7 28.0 35.5

70 80 90 100

104.2 116.3 128.3 140.2

100.4 112.3 124.1 135.8

95.0 106.6 118.1 129.6

90.5 101.9 113.1 124.3

85.5 96.6 107.6 118.5

77.6 88.1 98.6 109.1

69.3 79.3 89.3 99.3

61.7 71.1 80.6 90.1

55.3 64.3 73.3 82.4

51.7 60.4 69.1 77.9

48.8 57.2 65.6 74.2

45.4 53.5 61.8 70.1

43.3 51.2 59.2 67.3

in 40 will 9s2/␴ 2 be greater than 19.02. Consequently, it is not unlikely that s2 is a reliable estimate of ␴ 2. Stated differently: Upper limit:

␴ 2 ⫽ 9s2/2.7 ⫽ 3.3s2

Lower limit:

␴ 2 ⫽ 9s2/19.02 ⫽ 0.48s2

Ten measurements give an estimate of ␴ 2 that may be as much as 3.3 times or only about one-half the true variance.

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The F Statistic

The F statistic, along with the z, t, and ␹2 statistics, constitute the group that are thought of as fundamental statistics. Collectively they describe all the relationships that can exist between means and standard deviations. To perform an F test, we must first verify the randomness and independence of the errors. If ␴ 21 ⫽ ␴ 22 , then s21 /s22 will be distributed properly as the F statistic. If the calculated F is outside the confidence interval chosen for that statistic, then this is evidence that ␴ 21 ⫽ ␴ 22 . The F statistic describes the distribution of the ratios of variances of two sets of samples. It requires three table labels: the probability level and the two degrees of freedom. Since the F distribution requires a three-dimensional table which is effectively unknown, the F tables are presented as large sets of two-dimensional tables. The F distribution in Table 2.29 has the different numbers of degrees of freedom for the denominator variance placed along the vertical axis, while in each table the two horizontal axes represent the numerator degrees of freedom and the probability level. Only two probability levels are given in Table 2.29: the upper 5% points (F0.95) and the upper 1% points (F0.99). More extensive tables of statistics will list additional probability levels, and they should be consulted when needed. It is possible to compare the means of two relatively small sets of observations when the variances within the sets can be regarded as the same, as indicated by the F test. One can consider the distribution involving estimates of the true variance. With s 21 determined from a group of N1 observations and s 22 from a second group of N2 observations, the distribution of the ratio of the sample variances is given by the F statistic: F⫽

s 21 /␴ 21 s 22 /␴ 22

(2.16)

The larger variance is placed in the numerator. For example, the F test allows judgment regarding the existence of a significant difference in the precision between two sets of data or between two analysts. The hypothesis assumed is that both variances are indeed alike and a measure of the same ␴. The fact that each sample variance is related to its own population variance means that the sample variance being used for the calculation need not come from the same population. This is a significant departure from the assumptions inherent in the z, t, and ␹2 statistics. Example 12 Suppose Analyst A made five observations and obtained a standard deviation of 0.06, where Analyst B with six observations obtained sB ⫽ 0.03. The experimental variance ratio is: F⫽

(0.06)2 ⫽ 4.00 (0.03)2

From Table 2.28 with four degrees of freedom for A and five degrees of freedom for B, the value of F would exceed 5.19 five percent of the time. Therefore, the null hypothesis is valid, and comparable skills are exhibited by the two analysts. As applied in Example 12, the F test was one-tailed. The F test may also be applied as a twotailed test in which the alternative to the null hypothesis is ␴ 21 ⫽ ␴ 22. This doubles the probability that the null hypothesis is invalid and has the effect of changing the confidence level, in the above example, from 95% to 90%. If improvement in precision is claimed for a set of measurements, the variance for the set against which comparison is being made should be placed in the numerator, regardless of magnitude. An experimental F smaller than unity indicates that the claim for improved precision cannot be supported. The technique just given for examining whether the precision varies with the two different analytical procedures, also serves to compare the precision with different materials, or with different operators, laboratories, or sets of equipment.

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TABLE 2.29 F Distribution Interpolation should be performed using reciprocals of the degrees of freedom. Upper 5% points (F0.95)

1

2

3

4

5

6

7

8

9

10

12

15

20

24

30

40

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161 200 216 225 230 234 237 239 241 242 244 246 248 249 250 251 252 253 254 18.5 19.0 19.2 19.2 19.3 19.3 19.4 19.4 19.4 19.4 19.4 19.4 19.4 19.5 19.5 19.5 19.5 19.5 19.5 10.1 9.55 9.28 9.12 9.01 8.94 8.89 8.85 8.81 8.79 8.74 8.70 8.66 8.64 8.62 8.59 8.57 8.55 8.53 7.71 6.94 6.59 6.39 6.26 6.16 6.09 6.04 6.00 5.96 5.91 5.86 5.80 5.77 5.75 5.72 5.69 5.66 5.63 6.61 5.79 5.41 5.19 5.05 4.95 4.88 4.82 4.77 4.74 4.68 4.62 4.56 4.53 4.50 4.46 4.43 4.40 4.37 5.99 5.14 4.76 4.53 4.39 4.28 4.21 4.15 4.10 4.06 4.00 3.94 3.87 3.84 3.81 3.77 3.74 3.70 3.67 5.59 4.74 4.35 4.12 3.97 3.87 3.79 3.73 3.68 3.64 3.57 3.51 3.44 3.41 3.38 3.34 3.30 3.27 3.23 5.32 4.46 4.07 3.84 3.69 3.58 3.50 3.44 3.39 3.35 3.28 3.22 3.15 3.12 3.08 3.04 3.01 2.97 2.93 5.12 4.26 3.86 3.63 3.48 3.37 3.29 3.23 3.18 3.14 3.07 3.01 2.94 2.90 2.86 2.83 2.79 2.75 2.71 4.96 4.10 3.71 3.48 3.33 3.22 3.14 3.07 3.02 2.98 2.91 2.85 2.77 2.74 2.70 2.66 2.62 2.58 2.54 4.84 3.98 3.59 3.36 3.20 3.09 3.01 2.95 2.90 2.85 2.79 2.72 2.65 2.61 2.57 2.53 2.49 2.45 2.40 4.75 3.89 3.49 3.26 3.11 3.00 2.91 2.85 2.80 2.75 2.69 2.62 2.54 2.51 2.47 2.43 2.38 2.34 2.30 4.67 3.81 3.41 3.18 3.03 2.92 2.83 2.77 2.71 2.67 2.60 2.53 2.46 2.42 2.38 2.34 2.30 2.25 2.21 4.60 3.74 3.34 3.11 2.96 2.85 2.76 2.70 2.65 2.60 2.53 2.46 2.39 2.35 2.31 2.27 2.22 2.18 2.13 4.54 3.68 3.29 3.06 2.90 2.79 2.71 2.64 2.59 2.54 2.48 2.40 2.33 2.29 2.25 2.20 2.16 2.11 2.07 4.49 3.63 3.24 3.01 2.85 2.74 2.66 2.59 2.54 2.49 2.42 2.35 2.28 2.24 2.19 2.15 2.11 2.06 2.01 4.45 3.59 3.20 2.96 2.81 2.70 2.61 2.55 2.49 2.45 2.38 2.31 2.23 2.19 2.15 2.10 2.06 2.01 1.96 4.41 3.55 3.16 2.93 2.77 2.66 2.58 2.51 2.46 2.41 2.34 2.27 2.19 2.15 2.11 2.06 2.02 1.97 1.92 4.38 3.52 3.13 2.90 2.74 2.63 2.54 2.48 2.42 2.38 2.31 2.23 2.16 2.11 2.07 2.03 1.98 1.93 1.88 4.35 3.49 3.10 2.87 2.71 2.60 2.51 2.45 2.39 2.35 2.28 2.20 2.12 2.08 2.04 1.99 1.95 1.90 1.84 4.32 3.47 3.07 2.84 2.68 2.57 2.49 2.42 2.37 2.32 2.25 2.18 2.10 2.05 2.01 1.96 1.92 1.87 1.81 4.30 3.44 3.05 2.82 2.66 2.55 2.46 2.40 2.34 2.30 2.23 2.15 2.07 2.03 1.98 1.94 1.89 1.84 1.78 4.28 3.42 3.03 2.80 2.64 2.53 2.44 2.37 2.32 2.27 2.20 2.13 2.05 2.01 1.96 1.91 1.86 1.81 1.76 4.26 3.40 3.01 2.78 2.62 2.51 2.42 2.36 2.30 2.25 2.18 2.11 2.03 1.98 1.94 1.89 1.84 1.79 1.73 4.24 3.39 2.99 2.76 2.60 2.49 2.40 2.34 2.28 2.24 2.16 2.09 2.01 1.96 1.92 1.87 1.82 1.77 1.71 4.17 3.32 2.92 2.69 2.53 2.42 2.33 2.27 2.21 2.16 2.09 2.01 1.93 1.89 1.84 1.79 1.74 1.68 1.62 4.08 3.23 2.84 2.61 2.45 2.34 2.25 2.18 2.12 2.08 2.00 1.92 1.84 1.79 1.74 1.69 1.64 1.58 1.51 4.00 3.15 2.76 2.53 2.37 2.25 2.17 2.10 2.04 1.99 1.92 1.84 1.75 1.70 1.65 1.59 1.53 1.47 1.39 3.92 3.07 2.68 2.45 2.29 2.18 2.09 2.02 1.96 1.91 1.83 1.75 1.66 1.61 1.55 1.50 1.43 1.35 1.25 3.84 3.00 2.60 2.37 2.21 2.10 2.01 1.94 1.88 1.83 1.75 1.67 1.57 1.52 1.46 1.39 1.32 1.22 1.00

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TABLE 2.29 F Distribution (Continued) Upper 1% points (F0.99) Degrees of freedom for denominator

1

2

3

4

5

6

7

8

9

10

12

15

20

24

30

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INTERACTIVE

4052 5000 5403 5625 5764 5859 5928 5982 6023 6056 6106 6157 6209 6235 6261 6287 6313 6339 6366 98.5 99.0 99.2 99.2 99.3 99.3 99.4 99.4 99.4 99.4 99.4 99.4 99.4 99.5 99.5 99.5 99.5 99.5 99.5 34.1 30.8 29.5 28.7 28.2 27.9 27.7 27.5 27.3 27.2 27.1 26.9 26.7 26.6 26.5 26.4 26.3 26.2 26.1 21.2 18.0 16.7 16.0 15.5 15.2 15.0 14.8 14.7 14.5 14.4 14.2 14.0 13.9 13.8 13.7 13.7 13.6 13.5 16.3 13.3 12.1 11.4 11.0 10.7 10.5 10.3 10.2 10.1 9.89 9.72 9.55 9.47 9.38 9.29 9.20 9.11 9.02 13.7 10.9 9.78 9.15 8.75 8.47 8.26 8.10 7.98 7.87 7.72 7.56 7.40 7.31 7.23 7.14 7.06 6.97 6.88 12.2 9.55 8.45 7.85 7.46 7.19 6.99 6.84 6.72 6.62 6.47 6.31 6.16 6.07 5.99 5.91 5.82 5.74 5.65 11.3 8.65 7.59 7.01 6.63 6.37 6.18 6.03 5.91 5.81 5.67 5.52 5.36 5.28 5.20 5.12 5.03 4.95 4.86 10.6 8.02 6.99 6.42 6.06 5.80 5.61 5.47 5.35 5.26 5.11 4.96 4.81 4.73 4.65 4.57 4.48 4.40 4.31 10.0 7.56 6.55 5.99 5.64 5.39 5.20 5.06 4.94 4.85 4.71 4.56 4.41 4.33 4.25 4.17 4.08 4.00 3.91 9.65 7.21 6.22 5.67 5.32 5.07 4.89 4.74 4.63 4.54 4.40 4.25 4.10 4.02 3.94 3.86 3.78 3.69 3.60 9.33 6.93 5.95 5.41 5.06 4.82 4.64 4.50 4.39 4.30 4.16 4.01 3.86 3.78 3.70 3.62 3.54 3.45 3.36 9.07 6.70 5.74 5.21 4.86 4.62 4.44 4.30 4.19 4.10 3.96 3.82 3.66 3.59 3.51 3.43 3.34 3.25 3.17 8.86 6.51 5.56 5.04 4.70 4.46 4.28 4.14 4.03 3.94 3.80 3.66 3.51 3.43 3.35 3.27 3.18 3.09 3.00 8.68 6.36 5.42 4.89 4.56 4.32 4.14 4.00 3.89 3.80 3.67 3.52 3.37 3.29 3.21 3.13 3.05 2.96 2.87 8.53 6.23 5.29 4.77 4.44 4.20 4.03 3.89 3.78 3.69 3.55 3.41 3.26 3.18 3.10 3.02 2.93 2.84 2.75 8.40 6.11 5.19 4.67 4.34 4.10 3.93 3.79 3.68 3.59 3.46 3.31 3.16 3.08 3.00 2.92 2.83 2.75 2.65 8.29 6.01 5.09 4.58 4.25 4.01 3.84 3.71 3.60 3.51 3.37 3.23 3.08 3.00 2.92 2.84 2.75 2.66 2.57 8.19 5.93 5.01 4.50 4.17 3.94 3.77 3.63 3.52 3.43 3.30 3.15 3.00 2.92 2.84 2.76 2.67 2.58 2.49 8.10 5.85 4.94 4.43 4.10 3.87 3.70 3.56 3.46 3.37 3.23 3.09 2.94 2.86 2.78 2.69 2.61 2.52 2.42 8.02 5.78 4.87 4.37 4.04 3.81 3.64 3.51 3.40 3.31 3.17 3.03 2.88 2.80 2.72 2.64 2.55 2.46 2.36 7.95 5.72 4.82 4.31 3.99 3.76 3.59 3.45 3.35 3.26 3.12 2.98 2.83 2.75 2.67 2.58 2.50 2.40 2.31 7.88 5.66 4.76 4.26 3.94 3.71 3.54 3.41 3.30 3.21 3.07 2.93 2.78 2.70 2.62 2.54 2.45 2.35 2.26 7.82 5.61 4.72 4.22 3.90 3.67 3.50 3.36 3.26 3.17 3.03 2.89 2.74 2.66 2.58 2.49 2.40 2.31 2.21 7.77 5.57 4.68 4.18 3.86 3.63 3.46 3.32 3.22 3.13 2.99 2.85 2.70 2.62 2.53 2.45 2.36 2.27 2.17 7.56 5.39 4.51 4.02 3.70 3.47 3.30 3.17 3.07 2.98 2.84 2.70 2.55 2.47 2.39 2.30 2.21 2.11 2.01 7.31 5.18 4.31 3.83 3.51 3.29 3.12 2.99 2.89 2.80 2.66 2.52 2.37 2.29 2.20 2.11 2.02 1.92 1.80 7.08 4.98 4.13 3.65 3.34 3.12 2.95 2.82 2.72 2.63 2.50 2.35 2.20 2.12 2.03 1.94 1.84 1.73 1.60 6.85 4.79 3.95 3.48 3.17 2.96 2.79 2.66 2.56 2.47 2.34 2.19 2.03 1.95 1.86 1.76 1.66 1.53 1.38 6.63 4.61 3.78 3.32 3.02 2.80 2.64 2.51 2.41 2.32 2.18 2.04 1.88 1.79 1.70 1.59 1.47 1.32 1.00

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2.3.10

2.133

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Curve Fitting

Very often in practice a relationship is found (or known) to exist between two or more variables. It is frequently desirable to express this relationship in mathematical form by determining an equation connecting the variables. The first step is the collection of data showing corresponding values of the variables under consideration. From a scatter diagram, a plot of Y (ordinate) versus X (abscissa), it is often possible to visualize a smooth curve approximating the data. For purposes of reference, several types of approximating curves and their equations are listed. All letters other than X and Y represent constants. 1. Y ⫽ a0 ⫹ a1X

Straight line

2. Y ⫽ a0 ⫹ a1X ⫹ a2X2

Parabola or quadratic curve

3. Y ⫽ a0 ⫹ a1X ⫹ a2X ⫹ a3X 2

3

Cubic curve

4. Y ⫽ a0 ⫹ a1X ⫹ a2 ⫹ · · · ⫹ an Xn

nth degree curve

As other possible equations (among many) used in practice, these may be mentioned: 5. Y ⫽ (a0 ⫹ a1X)⫺1 or 1/Y ⫽ a0 ⫹ a1X

Hyperbola

6. Y ⫽ ab

or

log Y ⫽ log a ⫹ (log b)X

Exponential curve

7. Y ⫽ aXb or

log Y ⫽ log a ⫹ b log X

Geometric curve

X

8. Y ⫽ ab ⫹ g

Modified exponential curve

9. Y ⫽ aXn ⫹ g

Modified geometric curve

X

When we draw a scatter plot of all X versus Y data, we see that some sort of shape can be described by the data points. From the scatter plot we can take a basic guess as to which type of curve will best describe the X 9Y relationship. To aid in the decision process, it is helpful to obtain scatter plots of transformed variables. For example, if a scatter plot of log Y versus X shows a linear relationship, the equation has the form of number 6 above, while if log Y versus log X shows a linear relationship, the equation has the form of number 7. To facilitate this we frequently employ special graph paper for which one or both scales are calibrated logarithmically. These are referred to as semilog or log-log graph paper, respectively. 2.3.10.1 The Least Squares or Best-fit Line. The simplest type of approximating curve is a straight line, the equation of which can be written as in form number 1 above. It is customary to employ the above definition when X is the independent variable and Y is the dependent variable. To avoid individual judgment in constructing any approximating curve to fit sets of data, it is necessary to agree on a definition of a best-fit line. One could construct what would be considered the best-fit line through the plotted pairs of data points. For a given value of X1, there will be a difference D1 between the value Y1 and the constituent value Yˆ as determined by the calibration model. Since we are assuming that all the errors are in Y, we are seeking the best-fit line that minimizes the deviations in the Y direction between the experimental points and the calculated line. This condition will be met when the sum of squares for the differences, called residuals (or the sum of squares due to error),

冘 (Y ⫺ Yˆ ) ⬅ 冘 (D ⫹ D ⫹ · · · ⫹ D ) N

i⫽1

i

i

2

2 1

2 2

2 N

is the least possible value when compared to all other possible lines fitted to that data. If the sum of squares for residuals is equal to zero, the calibration line is a perfect fit to the data. With a

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mathematical treatment known as linear regression, one can find the “best” straight line through these real world points by minimizing the residuals. This calibration model for the best-fit fit line requires that the line pass through the “centroid” of the points (X, Y). It can be shown that:

冘 (X ⫺ X) (Y ⫺ Y) 冘 (X ⫺ X) i

b⫽

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i

i

(2.17)

2

i

i

a ⫽ Y ⫺ bX

(2.18)

The line thus calculated is known as the line of regression of Y on X, that is, the line indicating how Y varies when X is set to chosen values. If X is the dependent variable, the definition is modified by considering horizontal instead of vertical deviations. In general these two definitions lead to different least square curves. Example 13 The following data were recorded for the potential E of an electrode, measured against the saturated calomel electrode, as a function of concentration C (moles liter⫺1).

⫺log C

E, mV

⫺log C

E, mV

1.00 1.10 1.20 1.50 1.70 1.90

106 115 121 139 153 158

2.10 2.20 2.40 2.70 2.90 3.00

174 182 187 211 220 226

Fit the best straight line to these data; Xi represents ⫺log C, and Yi represents E. We will perform the calculation manually, using the following tabular lay-out.

Xi

Yi

(Xi ⫺ X)

(Xi ⫺ X)2

(Yi ⫺ Y)

(Xi ⫺ X)(Yi ⫺ Y)

1.00 1.10 1.20 1.50 1.70 1.90 2.10 2.20 2.40 2.70 2.90 3.00

106 115 121 139 153 158 174 182 187 211 220 226

⫺0.975 ⫺0.875 ⫺0.775 ⫺0.475 ⫺0.275 ⫺0.075 ⫹0.125 0.225 0.425 0.725 0.925 1.025

0.951 0.766 0.600 0.226 0.076 0.006 0.016 0.051 0.181 0.526 0.856 1.051

⫺60 ⫺51 ⫺45 ⫺27 ⫺13 ⫺8 8 16 21 45 54 60

58.5 44.6 34.9 12.8 3.6 0.6 1.0 3.6 8.9 32.6 50.0 61.5

兺Xi 23.7

兺Yi 1992

兺0

兺 5.306

兺0

兺 312.6

X ⫽ 1.975

Y ⫽ 166

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Now substituting the proper terms into Equation 17, the slope is: b⫽

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312.6 ⫽ 58.91 5.306

and from Equation 18, and substituting the “centroid” values of the points (X, Y), the intercept is: a ⫽ 166 ⫺ 58.91(1.975) ⫽ 49.64 The best-fit equation is therefore: E ⫽ 49.64 ⫺ 58.91 log C 2.3.10.2 Errors in the Slope and Intercept of the Best-fit Line. Upon examination of the plot of pairs of data points, the calibration line, it will be obvious that the precision involved in analyzing an unknown sample will be considerably poorer than that indicated by replicate error alone. The scatter of these original points about the calibration line is a good measure of the error to be expected in analyzing an unknown sample. And this same error is considerably larger than the replication error because it will include other sources of variability due to a variety of causes. One possible source of variability might be the presence of different amounts of an extraneous material in the various samples used to establish the calibration curve. While this variability causes scatter about the calibration curve, it will not be reflected in the replication error of any one sample if the sample is homogeneous. The scatter of the points around the calibration line or random errors are of importance since the best-fit line will be used to estimate the concentration of test samples by interpolation. The method used to calculate the random errors in the values for the slope and intercept is now considered. We must first calculate the standard deviation sY/X , which is given by:

sY/X ⫽

q

冘 (Y ⫺ Y)ˆ

2

i

i

(2.19)

N⫺2

Equation 19 utilizes the Y-residuals, Yi ⫺ Yˆ, where Yˆi are the points on the calculated best-fit line or the fitted Yi values. The appropriate number of degrees of freedom is N ⫺ 2; the minus 2 arises from the fact that linear calibration lines are derived from both a slope and an intercept which leads to a loss of two degrees of freedom. Now we can calculate the standard deviations for the slope and the intercept. These are given by: sb ⫽

sY/X

冘 (X ⫺ X) q

(2.20)

2

i

i

sa ⫽ sY/X

q

冘X N 冘 (X ⫺ X) 2 i

i

i

2

(2.21)

i

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The confidence limits for the slope are given by b ⫾ tb , where the t-value is taken at the desired confidence level and (N ⫺ 2) degrees of freedom. Similarly, the confidence limits for the intercept are given by a ⫾ tsa . The closeness of xˆ to xi is answered in terms of a confidence interval for x0 that extends from an upper confidence (UCL) to a lower confidence (LCL) level. Let us choose 95% for the confidence interval. Then, remembering that this is a two-tailed test (UCL and LCL), we obtain from a table of Student’s t distribution the critical value of tc (t0.975) and the appropriate number of degrees of freedom. Example 14 For the best-fit line found in Example 13, express the result in terms of confidence intervals for the slope and intercept. We will choose 95% for the confidence interval. The standard deviation sY/X is given by Equation 19, but first a supplementary table must be constructed for the Y residuals and other data which will be needed in subsequent equations.

Yˆ

(Yi ⫺ Yˆ )

(Yi ⫺ Yˆ )2

X 2i

108.6 114.4 120.3 138.0 149.8 161.6 173.4 179.2 191.0 208.7 220.5 226.4

2.55 ⫺0.56 ⫺0.67 ⫺1.00 ⫺3.21 3.57 ⫺0.65 ⫺2.76 4.02 ⫺2.30 0.48 0.40

6.50 0.31 0.45 1.00 10.32 12.94 0.42 7.61 16.16 5.30 0.23 0.16

1.00 1.21 1.44 2.25 2.89 3.61 4.41 4.84 5.76 7.29 8.41 9.00

兺 61.20

兺 52.11

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Now substitute the appropriate values into Equation 19 where there are 12 ⫺ 2 ⫽ 10 degrees of freedom: sX/Y ⫽

q

61.20 ⫽ 2.47 10

We can now calculate sb and sa from Equations 20 and 21, respectively: sb ⫽

sY/X p 5.31

⫽ 1.07

and sa ⫽ 2.47

q

52.11 ⫽ 2.23 12(5.306)

Now, using a two-tailed value for Student’s t: b ⫾ tsb ⫽ 58.91 ⫾ 2.23(1.07) ⫽ 58.91 ⫾ 2.39 a ⫾ tsa ⫽ 49.64 ⫾ 2.23(2.23) ⫽ 49.64 ⫾ 4.97

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The best-fit equation expressed in terms of the confidence intervals for the slope and intercept is:

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E ⫽ (49.64 ⫾ 5.0) ⫺ (58.91 ⫾ 2.43) log C To conclude the discussion about the best-fit line, the following relationship can be shown to exist among Y, Yˆ, and Y:

冘 (Y ⫺ Y) ⫽ 冘 (Yˆ ⫺ Y) ⫹ 冘 (Y ⫺ Yˆ ) N

i⫽1

N

i

2

i⫽1

N

i

2

i⫽1

i

i

2

(2.22)

The term on the left-hand side is a constant and depends only on the constituent values provided by the reference laboratory and does not depend in any way upon the calibration. The two terms on the right-hand side of the equation show how this constant value is apportioned between the two quantities that are themselves summations, and are referred to as the sum of squares due to regression and the sum of squares due to error. The latter will be the smallest possible value that it can possibly be for the given data.

2.3.11

Control Charts

It is often important in practice to know when a process has changed sufficiently so that steps may be taken to remedy the situation. Such problems arise in quality control where one must, often quickly, decide whether observed changes are due to simple chance fluctuations or to actual changes in the amount of a constituent in successive production lots, mistakes of employees, etc. Control charts provide a useful and simple method for dealing with such problems. The chart consists of a central line and two pairs of limit lines or simply of a central line and one pair of control limits. By plotting a sequence of points in order, a continuous record of the quality characteristic is made available. Trends in data or sudden lack of precision can be made evident so that the causes may be sought. The control chart is set up to answer the question of whether the data are in statistical control, that is, whether the data may be retarded as random samples from a single population of data. Because of this feature of testing for randomness, the control chart may be useful in searching out systematic sources of error in laboratory research data as well as in evaluating plant-production or controlanalysis data.1 To set up a control chart, individual observations might be plotted in sequential order and then compared with control limits established from sufficient past experience. Limits of ⫾1.96␴ corresponding to a confidence level of 95%, might be set for control limits. The probability of a future observation falling outside these limits, based on chance, is only 1 in 20. A greater proportion of scatter might indicate a nonrandom distribution (a systematic error). It is common practice with some users of control charts to set inner control limits, or warning limits, at ⫾1.96␴ and outer control limits of ⫾3.00␴. The outer control limits correspond to a confidence level of 99.8%, or a probability of 0.002 that a point will fall outside the limits. One-half of this probability corresponds to a high result and one-half to a low result. However, other confidence limits can be used as well; the choice in each case depends on particular circumstances. Special attention should be paid to one-sided deviation from the control limits, because systematic errors more often cause deviation in one direction than abnormally wide scatter. Two systematic errors of opposite sign would of course cause scatter, but it is unlikely that both would have entered at the same time. It is not necessary that the control chart be plotted in a time sequence. In any 1

G. Wernimont, Ind. Eng. Chem., Anal. Ed. 18:587 (1946); J. A. Mitchell, ibid. 19:961 (1947).

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situation where relatively large numbers of units or small groups are to be compared, the control chart is a simple means of indicating whether any unit or group is out of line. Thus laboratories, production machines, test methods, or analysts may be put arbitrarily into a horizontal sequence. Usually it is better to plot the means of small groups of observations on a control chart, rather than individual observations. The random scatter of averages of pairs of observations is 1/(2)1/2 ⫽ 0.71 as great as that of single observations, and the likelihood of two “wild” observations in the same direction is vanishing small. The groups of two to five observations should be chosen in such a way that only change variations operate within the group, whereas assignable causes are sought for variations between groups. If duplicate analyses are performed each day, the pairs form logical groups. Some measure of dispersion of the subgroup data should also be plotted as a parallel control chart. The most reliable measure of scatter is the standard deviation. For small groups, the range becomes increasingly significant as a measure of scatter, and it is usually a simple matter to plot the range as a vertical line and the mean as a point on this line for each group of observations.

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Bibliography Alder, H. L., and E. B. Roessler, Introduction to Probability and Statistics, W. H. Freeman, San Francisco, 1972. Bergmann, B., B. von Oepen, and P. Zinn, Anal. Chem., 59:2532 (1987). Box, G., W. Hunter, and J. Hunter, Statistics for Experimenters, Wiley, New York, 1978. Clayton, C. A., J. W. Hines, and P. D. Elkins, Anal. Chem., 59:2506 (1987). Caulcutt, R., and R. Boddy, Statistics for Analytical Chemists, Chapman and Hall, London, 1983. Dixon, W. J., and F. J. Massey, Introduction to Statistical Analysis, McGraw-Hill, New York, 1969. Hirsch, R. F. “Analysis of Variance in Analytical Chemistry,” Anal. Chem., 49:691A (1977). Jaffe, A. J., and H. F. Spirer, Misused Statistics—Straight Talk for Twisted Numbers, Marcel Dekker, New York, 1987. Linnig, F. J., and J. Mandel, “Which Measure of Precision?” Anal. Chem., 36:25A (1964). Mark, H., and J. Workman, Statistics in Spectroscopy, Academic Press, San Diego, CA, 1991. Meier, P. C., and R. E. Zund, Statistical Methods in Analytical Chemistry, Wiley, New York, 1993. Miller, J. C., and J. N. Miller, Statistics for Analytical Chemists, Halsted Press, John Wiley, New York, 1984. Moore, D. S., Statistics: Concepts and Controversies, W. H. Freeman, New York, 1985. Mulholland, H., and C. R. Jones, Fundamentals of Statistics, Plenum Press, New York, 1968. Taylor, J. K., Statistical Techniques for Data Analysis, Lewis, Boca Raton, FL, 1990. Youden, W. J., “The Sample, the Procedure, and the Laboratory,” Anal. Chem., 32:23A (1960). Youden, W. J., Statistical Methods for Chemists, Wiley, New York, 1951. Youden, W. J., Statistical Manual of the AOAC, AOAC, 1111 North 19th St., Arlington, VA, 22209.

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INORGANIC CHEMISTRY 3.1 NOMENCLATURE OF INORGANIC COMPOUNDS 3.1.1 Writing Formulas 3.1.2 Naming Compounds 3.1.3 Cations 3.1.4 Anions 3.1.5 Acids 3.1.6 Salts and Functional Derivatives of Acids Table 3.1 Trivial Names Retained for Acids 3.1.7 Coordination Compounds 3.1.8 Addition Compounds 3.2 PHYSICAL PROPERTIES OF PURE SUBSTANCES Table 3.2 Physical Constants of Inorganic Compounds Table 3.3 Synonyms and Mineral Names

3.1

3.1 3.1 3.3 3.6 3.6 3.8 3.8 3.9 3.10 3.11 3.12 3.12 3.61

NOMENCLATURE OF INORGANIC COMPOUNDS

The following synopsis of rules for naming inorganic compounds and the examples given in explanation are not intended to cover all the possible cases. For a more comprehensive and detailed description, see G. J. Leigh (ed.), Nomenclature of Inorganic Chemistry, 3d ed., Blackwell Scientific Publications, Oxford, 1990. This 289-page publication contains the Recommendations 1990 of the Commission on Nomenclature of Inorganic Chemistry and was prepared under the auspices of the International Union of Pure and Applied Chemistry (IUPAC). In particular, the latest report should be consulted for coordination compounds, boron compounds, and crystalline phases of variable composition.

3.1.1

Writing Formulas

3.1.1.1 Mass Number, Atomic Number, Number of Atoms, and Ionic Charge. The mass number, atomic number, number of atoms, and ionic charge of an element are indicated by means of four indices placed around the symbol: mass number ionic charge SYMBOL atomic number number of atoms

15 7

N23⫺

Ionic charge should be indicated by an Arabic superscript numeral preceding the plus or minus sign: Mg2 ⫹ , PO34⫺. 3.1.1.2 Placement of Atoms in a Formula. The electropositive constituent (cation) is placed first in a formula. If the compound contains more than one electropositive or more than one electronegative constituent, the sequence within each class should be in alphabetical order of their symbols. 3.1

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The alphabetical order may be different in formulas and names; for example, NaNH4HPO4 , ammonium sodium hydrogen phosphate. Acids are treated as hydrogen salts. Hydrogen is cited last among the cations. When there are several types of ligands, anionic ligands are cited before the neutral ligands.

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3.1.1.3 Binary Compounds between Nonmetals. For binary compounds between nonmetals, that constituent should be placed first which appears earlier in the sequence: Rn, Xe, Kr, Ar, Ne, He, B, Si, C, Sb, As, P, N, H, Te, Se, S, At, I, Br, Cl, O, F Examples: AsCl3 , SbH3 , H3Te, BrF3 , OF2 , and N4 S4 . 3.1.1.4 Chain Compounds. For chain compounds containing three or more elements, the sequence should be in accordance with the order in which the atoms are actually bound in the molecule or ion. Examples: SCN⫺ (thiocyanate), HSCN (hydrogen thiocyanate or thiocyanic acid), HNCO (hydrogen isocyanate), HONC (hydrogen fulminate), and HPH2O2 (hydrogen phosphinate). 3.1.1.5 Use of Centered Period. A centered period is used to denote water of hydration, other solvates, and addition compounds; for example, CuSO4 · 5H2O, copper(II) sulfate 5-water (or pentahydrate). 3.1.1.6 Free Radicals. In the formula of a polyatomic radical an unpaired electron(s) is(are) indicated by a dot placed as a right superscript to the parentheses (or square bracket for coordination compounds). In radical ions the dot precedes the charge. In structural formulas, the dot may be placed to indicate the location of the unpaired electron(s). (HO)D

Examples:

(O2 )2D

(NH B ⫹3 )

3.1.1.7 Enclosing Marks. Where it is necessary in an inorganic formula, enclosing marks (parentheses, braces, and brackets) are nested within square brackets as follows: [ ( ) ],

[ { ( ) } ],

[ { [ ( ) ] } ],

[{{[()]}}]

In an inorganic name the nesting order is different: { { { [ ( ) ] } } }, and so on. 3.1.1.8 Molecular Formula. For compounds consisting of discrete molecules, a formula in accordance with the correct molecular weight of the compound should be used. Examples: S2Cl2 , S8 , N2O4 , and H4P2O6 ; not SCl, S, NO2 , and H2PO3 . 3.1.1.9 Structural Formula and Prefixes. In the structural formula the sequence and spatial arrangement of the atoms in a molecule are indicated. Examples: NaO(O "C)H (sodium formate), Cl 9S9S9 Cl (disulfur dichloride). Structural prefixes should be italicized and connected with the chemical formula by a hyphen: cis-, trans-, anti-, syn-, cyclo-, catena-, o- or ortho-, m- or meta-, p- or para-, sec- (secondary), tert(tertiary), v- (vicinal), meso-, as- for asymmetrical, and s- for symmetrical. The sign of optical rotation is placed in parentheses, (⫹) for dextrorotary, (⫺) for levorotary, and (⫾) for racemic, and placed before the formula. The wavelength (in nanometers is indicated by a right subscript; unless indicated otherwise, it refers to the sodium D-line.

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The italicized symbols d- (for deuterium) and t- (for tritium) are placed after the formula and connected to it by a hyphen. The number of deuterium or tritium atoms is indicated by a subscript to the symbol. Examples:

cis-[PtCl2(NH3)2]

methan-d3-ol

di-tert-butyl sulfate

(⫹)589[Co(en)3]Cl2

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methan-ol-d

3.1.2

Naming Compounds

3.1.2.1 Names and Symbols for Elements. Names and symbols for the elements are given in Table 3.2. Wolfram is preferred to tungsten but the latter is used in the United States. In forming a complete name of a compound, the name of the electropositive constituent is left unmodified except when it is necessary to indicate the valency (see oxidation number and charge number, formerly the Stock and Ewens-Bassett systems). The order of citation follows the alphabetic listing of the names of the cations followed by the alphabetical listing of the anions and ligands. The alphabetical citation is maintained regardless of the number of each ligand. Example: K[AuS(S2)] is potassium (disulfido)thioaurate(1⫺). 3.1.2.2 Electronegative Constituents. The name of a monatomic electronegative constituent is obtained from the element name with its ending (-en, -ese, -ic, -ine, -ium, -ogen, -on, -orus, -um, -ur, -y, or -ygen) replaced by -ide. The elements bismuth, cobalt, nickel, zinc, and the noble gases are used unchanged with the ending -ide. Homopolyatomic ligands will carry the appropriate prefix. A few Latin names are used with affixes: cupr- (copper), aur- (gold), ferr- (iron), plumb- (lead), argent- (silver), and stann- (tin). For binary compounds the name of the element standing later in the sequence in Sec. 3.1.1.3 is modified to end in -ide. Elements other than those in the sequence of Sec. 3.1.1.3 are taken in the reverse order of the following sequence, and the name of the element occurring last is modified to end in -ide; e.g., calcium stannide. ELEMENT SEQUENCE

3.1.2.3 Stoichiometric Proportions. The stoichiometric proportions of the constituents in a formula may be denoted by Greek numerical prefixes: mono-, di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona- (Latin), deca-, undeca- (Latin), dodeca-, . . . , icosa- (20), henicosa- (21), . . . , triconta- (30), tetraconta- (40), . . . , hecta- (100), and so on, preceding without a hyphen the names of the elements to which they refer. The prefix mono can usually be omitted; occasionally hemi(1⁄2) and sesqui- (3⁄2) are used. No elisions are made when using numerical prefixes except in the case of icosa- when the letter “i” is elided in docosa- and tricosa-. Beyond 10, prefixes may be replaced by Arabic numerals.

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When it is required to indicate the number of entire groups of atoms, the multiplicative numerals bis-, tris-, tetrakis-, pentakis-, and so on, are used (i.e., -kis is added starting from tetra-). The entity to which they refer is placed in parentheses.

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Examples: Ca[PF6]2 , calcium bis(hexafluorophosphate); and (C10H21)3PO4 , tris(decyl) phosphate instead of tridecyl which is (C13H27⫺). Composite numeral prefixes are built up by citing units first, then tens, then hundreds, and so on. For example, 43 is written tritetraconta- (or tritetracontakis-). In indexing it may be convenient to italicize a numerical prefix at the beginning of the name and connect it to the rest of the name with a hyphen; e.g., di-nitrogen pentaoxide (indexed under the letter “n”). 3.1.2.4 Oxidation and Charge Numbers. The oxidation number (Stock system) of an element is indicated by a Roman numeral placed in parentheses immediately following the name of the element. For zero, the cipher 0 is used. When used in conjunction with symbols the Roman numeral may be placed above and to the right. The charge number of an ion (Ewens-Bassett system) rather than the oxidation state is indicated by an Arabic numeral followed by the sign of the charge cited and is placed in parentheses immediately following the name of the ion. Examples: P2O5 , diphosphorus pentaoxide or phosphorus(V) oxide; Hg22 ⫹ , mercury(I) ion or dimercury(2⫹) ion; K2[Fe(CN)6], potassium hexacyanoferrate(II) or potassium hexacyanoferrate(4⫺); PbII2 PbIVO4, dilead(II) lead(IV) oxide or trilead tetraoxide. Where it is not feasible to define an oxidation state for each individual member of a group, the overall oxidation level of the group is defined by a formal ionic charge to avoid the use of fractional oxidation states; for example, O⫺2 . 3.1.2.5

Collective Names. Collective names include:

Halogens (F, Cl, Br, I, At) Chalcogens (O, S, Se, Te, Po) Alkali metals (Li, Na, K, Rb, Cs, Fr) Alkaline-earth metals (Ca, Sr, Ba, Ra) Lanthanoids or lanthanides (La to Lu) Rare-earth metals (Sc, Y, and La to Lu inclusive) Actinoids or actinides (Ac to Lr, those whose 5f shell is being filled) Noble gases (He to Rn) A transition element is an element whose atom has an incomplete d subshell, or which gives rise to a cation or cations with an incomplete d subshell. 3.1.2.6 Isotopically Labeled Compounds. The hydrogen isotopes are given special names: 1H (protium), 2H or D (deuterium), and 3H or T (tritium). The superscript designation is preferred because D and T disturb the alphabetical ordering in formulas. Other isotopes are designated by mass numbers: 10B (boron-10). Isotopically labeled compounds may be described by inserting the italic symbol of the isotope in brackets into the name of the compound; for example, H36Cl is hydrogen chloride[36Cl] or hydrogen chloride-36, and 2H38Cl is hydrogen [2H] chloride[38Cl] or hydrogen-2 chloride-38.

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3.1.2.7 Allotropes. Systematic names for gaseous and liquid modifications of elements are sometimes needed. Allotropic modifications of an element bear the name of the atom together with the descriptor to specify the modification. The following are a few common examples:

Symbol

Trivial name

Systematic name

H O2 O3 P4 S8 Sn

Atomic hydrogen (Common oxygen) Ozone White phosphorus ␣-Sulfur, ␤-Sulfur ␮-Sulfur (plastic sulfur)

Monohydrogen Dioxygen Trioxygen Tetraphosphorus Octasulfur Polysulfur

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Trivial (customary) names are used for the amorphous modification of an element. 3.1.2.8 Heteroatomic and Other Anions. A few heteroatomic anions have names ending in -ide. These are 9OH, hydroxide ion (not hydroxyl)

9NH9, imide ion

9 CN, cyanide ion

9 NH9NH2 , hydrazide ion

9 HF⫺2 , hydrogen difluoride ion

9NHOH, hydroxylamide ion

9NH2 , amide ion

9HS⫺, hydrogen sulfide ion

Added to these anions are 9 I⫺3 , triiodide ion

9O9O 9, peroxide ion

9N3 , azide ion

9 S9S9, disulfide ion

9O3 , ozonide ion 3.1.2.9 Binary Compounds of Hydrogen. Binary compounds of hydrogen with the more electropositive elements are designated hydrides (NaH, sodium hydride). Volatile hydrides, except those of Periodic Group VII and of oxygen and nitrogen, are named by citing the root name of the element (penultimate consonant and Latin affixes, Sec. 3.1.2.2) followed by the suffix -ane. Exceptions are water, ammonia, hydrazine, phosphine, arsine, stibine, and bismuthine. Examples: B2H6 , diborane; B10H14 , decaborane(14); B10H16, decaborane(16); P2H4 , diphosphane; Sn2H6 , distannane; H2Se2 , diselane; H2Te2 , ditellane; H2S5 , pentasulfane; and PbH4 , plumbane. 3.1.2.10

Neutral Radicals. Certain neutral radicals have special names ending in -yl:

HO

hydroxyl

ClO3

perchloryl*

CO

carbonyl

CrO2

chromyl

ClO

chlorosyl*

NO

ClO2

chloryl*

NO2

* Similarly for the other halogens.

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PO

phosphoryl

SeO

SO

sulfinyl (thionyl)

SeO2

selenonyl

UO2

uranyl

SO2 S2O5

sulfonyl (sulfuryl) disulfuryl

NpO2

seleninyl

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neptunyl†

Radicals analogous to the above containing other chalcogens in place of oxygen are named by adding the prefixes thio-, seleno-, and so on; for example, PS, thiophosphoryl; CS, thiocarbonyl. 3.1.3

Cations

3.1.3.1 Monatomic Cations. Monatomic cations are named as the corresponding element; for example, Fe2⫹, iron(II) ion; Fe3⫹, iron(III) ion. This principle also applies to polyatomic cations corresponding to radicals with special names ending in -yl (Sec. 3.1.2.10); for example, PO⫹, phosphoryl cation; NO⫹, nitrosyl cation; NO22⫹, nitryl cation; O22⫹, oxygenyl cation. Use of the oxidation number and charge number extends the range for radicals; for example, UO22⫹ uranyl(VI) or uranyl(2⫹) cation; UO2⫹, uranyl(V) or uranyl(1⫹) cation. 3.1.3.2 Polyatomic Cations. Polyatomic cations derived by addition of more protons than required to give a neutral unit to polyatomic anions are named by adding the ending -onium to the root of the name of the anion element; for example, PH⫹4 , phosphonium ion; H2I⫹, iodonium ion; H3O⫹, oxonium ion; CH3OH2⫹, methyl oxonium ion. Exception: The name ammonium is retained for the NH⫹4 ion; similarly for substituted ammonium ions; for example, NF⫹4 , tetrafluoroammonium ion. Substituted ammonium ions derived from nitrogen bases with names ending in -amine receive names formed by changing -amine into -ammonium. When known by a name not ending in -amine, the cation name is formed by adding the ending -ium to the name of the base (eliding the final vowel); e.g., anilinium, hydrazinium, imidazolium, acetonium, dioxanium. Exceptions are the names uronium and thiouronium derived from urea and thiourea, respectively. 3.1.3.3 Multiple Ions from One Base. Where more than one ion is derived from one base, the ionic charges are indicated in their names: N2H5⫹, hydrazinium(1⫹) ion; N2H26⫹, hydrazinium(2⫹) ion. 3.1.4

Anions

See Secs. 3.1.2.2 and 3.1.2.8 for naming monatomic and certain polyatomic anions. When an organic group occurs in an inorganic compound, organic nomenclature (q.v.) is followed to name the organic part. 3.1.4.1 Protonated Anions. Ions such as HSO⫺4 are recommended to be named hydrogensulfate with the two words written as one following the usual practice for polyatomic anions. However, in the Nomenclature of Organic Chemistry, 1979 edition, hydrogen is used as a separate word; this practice is followed in this Handbook.

† Similarly for the other actinoid elements.

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3.1.4.2 Other Polyatomic Anions. Names for other polyatomic anions consist of the root name of the central atom with the ending -ate and followed by the valence of the central atom expressed by its oxidation number. Atoms and groups attached to the central atom are treated as ligands in a complex.

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Examples: [Sb(OH)⫺6 ], hexahydroxoantimonate(V); [Fe(CN6]3⫺, hexacyanoferrate(III); [Co(NO2)6]3⫺, hexanitritocobaltate(III); [TiO(C2O4)2(H2O)2]2⫺, oxobisoxalatodiaquatitanate(IV); [PCl6]⫺, hexachlorophosphate(V). Exceptions to the use of the root name of the central atom are antimonate, bismuthate, carbonate, cobaltate, nickelate (or niccolate), nitrate, phosphate, tungstate (or wolframate), and zincate. 3.1.4.3 Anions of Oxygen. Oxygen is treated in the same manner as other ligands with the number of -oxo groups indicated by a suffix; for example, SO23⫺, trioxosulfate. The ending -ite, formerly used to denote a lower state of oxidation, may be retained in trivial names in these cases (note Sec. 3.1.5.3 also): AsO33⫺

arsenite

NOO⫺2

peroxonitrite

BrO⫺

hypobromite

PO33⫺

phosphite*

ClO⫺

hypochlorite

SO23⫺

sulfite

ClO⫺2

chlorite

S2O25⫺

⫺

IO

hypoiodite

NO⫺2

nitrite

2⫺ 2

N2O

hyponitrite

disulfite

2⫺ 4

dithionite

S2O22⫺

thiosulfite

S2O

2⫺ 3

SeO

selenite

However, compounds known to be double oxides in the solid state are named as such; for example, Cr2CuO4 (actually Cr2O3 · CuO) is chromium(III) copper(II) oxide (and not copper chromite). 3.1.4.4 Isopolyanions. Isopolyanions are named by indicating with numerical prefixes the number of atoms of the characteristic element. It is not necessary to give the number of oxygen atoms when the charge of the anion or the number of cations is indicated. Examples: Ca3Mo7O24 , tricalcium 24-oxoheptamolybdate, may be shortened to tricalcium heptamolybdate; the anion, Mo7O624⫺, is heptamolybdate(6⫺); S2O27⫺, disulfate(2⫺); P2O47⫺, diphosphate(V)(4⫺). When the characteristic element is partially or wholly present in a lower oxidation state than corresponds to its Periodic Group number, oxidation numbers are used; for example, [O2HP9O 9 PO3H]2⫺, dihydrogendiphosphate(III,V)(2⫺). A bridging group should be indicated by adding the Greek letter ␮ immediately before its names and separating this from the rest of the complex by a hyphen. The atom or atoms of the characteristic element to which the bridging atom is bonded, is indicated by numbers. Examples:

[O3P9S9PO2 9 O9 PO3]5⫺, 1,2-␮-thiotriphosphate(5⫺) [S3P9O9PS2 9O9 PS3]5⫺, di-␮-oxo-octathiotriphosphate(5⫺)

* Named for esters formed from the hypothetical acid P(OH)3 .

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Acids

3.1.5.1 Acids and -ide Anions. Acids giving rise to the -ide anions (Sec. 3.1.2.2) should be named as hydrogen . . . -ide; for example, HCl, hydrogen chloride; HN3 , hydrogen azide. Names such as hydrobromic acid refer to an aqueous solution, and percentages such as 48% HBr denote the weight/volume of hydrogen bromide in the solution. 3.1.5.2 Acids and -ate Anions. Acids giving rise to anions bearing names ending in -ate are treated as in Sec. 3.1.5.1; for example, H2GeO4 , hydrogen germanate; H4[Fe(CN)6], hydrogen hexacyanoferrate(II). 3.1.5.3 Trivial Names. Acids given in Table 3.1 retain their trivial names due to long-established usage. Anions may be formed from these trivial names by changing -ous acid to -ite, and -ic acid to -ate. The prefix hypo- is used to denote a lower oxidation state and the prefix per- designates a higher oxidation state. The prefixes ortho- and meta- distinguish acids of differing water content; for example, H4SiO4 is orthosilicic acid and H2SiO3 is metasilicic acid. The anions would be named silicate(4⫺) and silicate(2⫺), respectively. 3.1.5.4 Peroxo- Group. When used in conjunction with the trivial names of acids, the prefix peroxo- indicates substitution of 9O 9 by 9O 9 O 9. 3.1.5.5 Replacement of Oxygen by Other Chalcogens. Acids derived from oxoacids by replacement of oxygen by sulfur are called thioacids, and the number of replacements are given by prefixes di-, tri-, and so on. The affixes seleno- and telluro- are used analogously. Examples: HOO 9 C" S, thiocarbonic acid; HSS 9C"S, trithiocarbonic acid. 3.1.5.6 Ligands Other than Oxygen and Sulfur. See Sec. 3.1.7, Coordination Compounds, for acids containing ligands other than oxygen and sulfur (selenium and tellurium). 3.1.5.7 Differences between Organic and Inorganic Nomenclature. Organic nomenclature is largely built upon the scheme of substitution, that is, the replacement of hydrogen atoms by other atoms or groups. Although rare in inorganic nomenclature: NH2Cl is called chloramine and NHCl2 dichloroamine. Other substitutive names are fluorosulfonic acid and chlorosulfonic acid derived from HSO3H. These and the names aminosulfonic acid (sulfamic acid), iminodisulfonic acid, and nitrilotrisulfonic acid should be replaced by the following based on the concept that these names are formed by adding hydroxyl, amide, imide, and so on, groups together with oxygen atoms to a sulfur atom: HSO3F

fluorosulfuric acid

HSO3Cl NH2SO3H 3.1.6

chlorosulfuric acid

NH(SO3H)2 N(SO3H)3

imidobis(sulfuric) acid nitridotris(sulfuric) acid

amidosulfuric acid

Salts and Functional Derivatives of Acids

3.1.6.1 Acid Halogenides. For acid halogenides the name is formed from the corresponding acid radical if this has a special name (Sec. 3.1.2.10); for example, NOCl, nitrosyl chloride. In other cases these compounds are named as halogenide oxides with the ligands listed alphabetically; for example, BiClO, bismuth chloride oxide; VCl2O, vanadium(IV) dichloride oxide. 3.1.6.2 Anhydrides. Anhydrides of inorganic acids are named as oxides; for example, N2O5 , dinitrogen pentaoxide.

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TABLE 3.1 Trivial Names Retained for Acids Alphabetically by characteristic element. H3AsO4 H3AsO3 H3BO3 HBO2 HBrO3 HBrO2 HBrO H2CO3 HOCN HNCO HONC HClO4 HClO3 HClO2 HClO H2CrO4 H2Cr2O7 H5IO6 HIO4 HIO3 HIO HMnO4 H2MnO4 HNO4 HNO3 HNO2 H2NO2 H2N2O2 HOONO H3PO4 HPO3 H3PO5

arsenic acid arsenious acid orthoboric acid (or boric acid) metaboric acid bromic acid bromous acid hypobromous acid carbonic acid cyanic acid isocyanic acid fulminic acid perchloric acid chloric acid chlorous acid hypochlorous acid chromic acid dichromic acid orthoperiodic acid periodic acid iodic acid hypoiodous acid permanganic acid manganic acid peroxonitric acid nitric acid nitrous acid nitroxylic acid hyponitrous acid peroxonitrous acid orthophosphoric acid (or phosphoric acid) metaphosphoric acid peroxomonophosphoric acid

H4P2O7 H4P2O8 (HO)2OP (HO)2OP (HO)2P 9 O

diphosphoric acid (or pyrophosphoric acid) peroxodiphosphoric acid diphosphoric(IV) acid or hypophosphoric acid diphosphoric(III,V) acid

(HO)2P 9 O H2PHO3 H2P2H2O5 HPH2O2

phosphonic acid diphosphonic acid phosphinic acid (formerly hypophosphorous acid) HReO4 perrhenic acid H2ReO4 rhenic acid H2SO4 sulfuric acid H2S2O7 disulfuric acid H2SO5 peroxomonosulfuric acid H2S2O3 thiosulfuric acid H2S2S6 dithionic acid H2SO3 sulfurous acid H2S2O5 disulfurous acid H2S2O2 thiosulfurous acid H2S2O4 dithionous acid H2SxO6 polythionic acid (x ⫽ 3, 4, . . . ) (tri-, tetra-, . . . ) H2SO2 sulfoxylic acid HSb(OH)6 hexahydrooxoantimonic acid H2SeO4 selenic acid H2SeO3 selenious acid H4SiO4 orthosilicic acid H2SiO3 metasilicic acid HTcO4 pertechnetic acid H2TeO4 technetic acid H6TeO6 orthotelluric acid

3.1.6.3 Esters. Esters of inorganic acids are named as the salts; for example, (CH3)2SO4 , dimethyl sulfate. However, if it is desired to specify the constitution of the compound, the nomenclature for coordination compounds should be used. 3.1.6.4 Amides. Names for amides are derived from the names of the acid radicals (or from the names of acids by replacing acid by amide); for example, SO2(NH2)2 , sulfonyl diamide (or sulfuric diamide); NH2SO3H, sulfamidic acid (or amidosulfuric acid). 3.1.6.5 Salts. Salts containing acid hydrogen are named by adding the word hydrogen before the name of the anion (however, see Sec. 3.1.4.1), for example, KH2PO4 , potassium dihydrogen phosphate; NaHCO3 , sodium hydrogen carbonate (not bicarbonate); NaHPHO3 , sodium hydrogen phosphonate (only one acid hydrogen remaining). Salts containing O2⫺ and HO⫺ anions are named oxide and hydroxide, respectively. Anions are cited in alphabetical order which may be different in formulas and names. Examples: FeO(OH), iron(III) hydroxide oxide; VO(SO4), vanadium(IV) oxide sulfate.

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SECTION 3

3.1.6.6 Multiplicative Prefixes. The multiplicative prefixes bis, tris, etc., are used with certain anions for indicating stoichiometric proportions when di, tri, etc., have been preempted to designate condensed anions; for example, AlK(SO4)2 · 12H2O, aluminum potassium bis(sulfate) 12-water (recall that disulfate refers to the anion S2O27⫺).

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3.1.6.7 Crystal Structure. The structure type of crystals may be added in parentheses and in italics after the name; the latter should be in accordance with the structure. When the typename is also the mineral name of the substance itself, italics are not used. Examples: MgTiO3 , magnesium titanium trioxide (ilmenite type); FeTiO3 , iron(II) titanium trioxide (ilmenite).

3.1.7

Coordination Compounds

3.1.7.1 Naming a Coordination Compound. To name a coordination compound, the names of the ligands are attached directly in front of the name of the central atom. The ligands are listed in alphabetical order regardless of the number of each and with the name of a ligand treated as a unit. Thus “diammine” is listed under “a” and “dimethylamine” under “d.” The oxidation number of the central atom is stated last by either the oxidation number or charge number. 3.1.7.2 Anionic Ligands. Whether inorganic or organic, the names for anionic ligands end in -o (eliding the final -e, if present, in the anion name). Enclosing marks are required for inorganic anionic ligands containing numerical prefixes, and for thio, seleno, and telluro analogs of oxo anions containing more than one atom. If the coordination entity is negatively charged, the cations paired with the complex anion (with -ate ending) are listed first. If the entity is positively charged, the anions paired with the complex cation are listed immediately afterward. The following anions do not follow the nomenclature rules: F⫺

fluoro

HO⫺2

hydrogen peroxo

⫺

Cl

chloro

S

thio (only for single sulfur)

Br⫺

bromo

S22⫺

disulfido

I⫺ O2⫺ ⫺

H

OH⫺ O22⫺

iodo oxo hydrido (or hydro) hydroxo

2⫺

HS⫺

mercapto

CN⫺

cyano ⫺

CH2O

methoxo or methanolato

CH2S⫺

methylthio or methanethiolato

peroxo

3.1.7.3 Neutral and Cationic Ligands. Neutral and cationic ligands are used without change in name and are set off with enclosing marks. Water and ammonia, as neutral ligands, are called “aqua” and “ammine,” respectively. The groups NO and CO, when linked directly to a metal atom, are called nitrosyl and carbonyl, respectively. 3.1.7.4 Attachment Points of Ligands. The different points of attachment of a ligand are denoted by adding italicized symbol(s) for the atom or atoms through which the attachment occurs at the end of the name of the ligand; e.g., glycine-N or glycinato-O,N. If the same element is involved in different possible coordination sites, the position in the chain or ring to which the element is attached is indicated by numerical superscripts: e.g., tartrato(3⫺)-O1,O2, or tartrato(4⫺)-O2,O3 or tartrato(2⫺)-O1,O4.

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3.1.7.5 Abbreviations for Ligand Names. Except for certain hydrocarbon radicals, for ligand (L) and metal (M), and a few with H, all abbreviations are in lowercase letters and do not involve hyphens. In formulas, the ligand abbreviation is set off with parentheses. Some common abbreviations are Ac acac Hacac

acetyl

en

acetylacetonato acetylacetone

Him H2ida

Hba

benzoylacetone

Me

Bzl

benzyl

H3nta

Hbg

biguanide

nbd

bpy

2,2⬘-bipyridine

ox

Bu

butyl

phen

Cy

cyclohexyl

Ph

D2dea

imidazole iminodiacetic acid methyl nitrilotriacetic acid norbornadiene oxalato(2⫺) from parent H2ox 1,10-phenanthroline phenyl

diethanolamine

pip

diethylenetriamine

Pr

propyl

dmf

dimethylformamide

pn

propylenediamine

dmg Hdmg dmso Et

dimethylglyoxime dimethylglyoximato(2⫺) dimethylglyoximato(1⫺) dimethylsulfoxide ethyl

H4edta

Hea

coordinated ions derived from H4edta

ethanolamine

piperidine

pyrazole

py

pyridine

thf

tetrahydrofuran

tu H3tea

ethylenediaminetetraacetic acid

Hedta, edta

Hpz

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ethylenediamine

dien H2dmg

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thiourea triethanolamine

tren

2,2⬘,2⬙-triaminotriethylamine

trien

triethylenetetraamine

tn

trimethylenediamine

ur

urea

Examples: Li[B(NH2)4], lithium tetraamidoborate(1⫺) or lithium tetraamidoborate(III); [Co(NH3)5Cl]Cl3 , pentaamminechlorocobalt(III) chloride or pentaamminechlorocobalt(2⫹) chloride; K3[Fe(CN)5CO], potassium carbonylpentacyanoferrate(II) or potassium carbonylpentacyanoferrate(3⫺); [Mn{C6H4(O)(COO)}2(H2O)4]⫺, tetraaquabis[salicylato(2⫺)]manganate(III) ion; [Ni(C4H7N2O2)2] or [Ni(dmg)] which can be named bis-(2,3-butanedione dioximato)nickel(II) or bis[dimethylglyoximato(2⫺)]nickel(II).

3.1.8

Addition Compounds

The names of addition compounds are formed by connecting the names of individual compounds by a dash (— ) and indicating the numbers of molecules in the name by Arabic numerals separated by the solidus (diagonal slash). All molecules are cited in order of increasing number; those having the same number are cited in alphabetic order. However, boron compounds and water are always cited last and in that order. Examples: 3CdSO4 · 8H2O, cadmium sulfate— water (3/8); Al2(SO4)3 · K2SO4 · 24H2O, aluminum sulfate— potassium sulfate— water (1/1/24); AlCl3 · 4C2H5OH, aluminum chloride— ethanol (1/4).

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PHYSICAL PROPERTIES OF PURE SUBSTANCES

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TABLE 3.2 Physical Constants of Inorganic Compounds Names follow the IUPAC Nomenclature. Solvates are listed under the entry for the anhydrous salt. Acids are entered under Hydrogen and acid salts are entered as a subentry under hydrogen. Formula weights are based upon the International Atomic Weights of 1993 and are computed to the nearest hundredth when justified. The actual significant figures are given in the atomic weights of the individual elements. Each element that has neither a stable isotope nor a characteristic natural isotopic composition is represented in this table by one of that element’s commonly known radioisotopes identified by mass number and relative atomic mass. Density values are given at room temperature unless otherwise indicated by the superscript figure; for example, 2.48715 indicates a density of 2.487 g/cm3 for the substance at 15⬚C. A superscript 20 over a subscript 4 indicates a density at 20⬚C relative to that of water at 4⬚C. For gases the values are given as grams per liter (g/L). Melting point is recorded in a certain case as 250 d and in some other cases as d 250, the distinction being made in this manner to indicate that the former is a melting point with decomposition at 250⬚C while in the latter decomposition only occurs at 250⬚C and higher temperatures. Where a value such as ⫺6H2O, 150 is given it indicates a loss of 6 moles of water per formula weight of the compound at a temperature of 150⬚C. For hydrates the temperature stated represents the compound melting in its water of hydration. Boiling point is given at atmospheric pressure (760 mm of mercury or 101 325 Pa) unless otherwise indicated; thus 8215mm indicates that the boiling point is 82⬚C when the pressure is 15 mm of mercury. Also, subl 550 indicates that the compound sublimes at 550⬚C. Occasionally decomposition products are mentioned. Solubility is given in parts by weight (of the formula weight) per 100 parts by weight of the solvent (i.e., percent by weight) and at room temperature. Another unit frequently used is grams per 100 mL of solvent (mL per 100 mL for liquids and gases). The symbols of the common mineral acids represent aqueous solutions of these acids. Abbreviations Used in the Table a, acid abs, absolute abs alc, anhydrous ethanol acet, acetone alk, alkali (aq NaOH or KOH) anhyd, anhydrous aq, aqueous aq reg, aqua regia atm, atmosphere BuOH, butanol bz, benzene c, solid state ca., approximately chl, chloroform conc, concentrated cub, cubic d, decomposes dil, dilute disprop, disproportionates EtOAc, ethyl acetate eth, diethyl ether EtOH, 95% ethanol expl, explodes fcc, face-centered cubic fctetr, face-centered tetragonal FP, flash point fum, fuming fus, fusion, fuses g, gas, gram glyc, glycerol

h, hot hex, hexagonal HOAc, acetic acid i, insoluble ign, ignites L, liter lq, liquid MeOH, methanol min, mineral mL, milliliter org, organic oxid, oxidizing PE, petroleum ether pyr, pyridine s, soluble satd, saturated sl, slightly soln, solution solv, solvent(s) subl, sublimes sulf, sulfides tart, tartrate THF, tetrahyrofuran v, very vac, vacuum viol, violently volat, volatilizes ⬍, less than ⬎, greater than

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TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Density

227.0278 466.74 26.981539 324.31 453.33

10.07 5.85 2.70 1.27 1.65

AlSb AlAs Al(OOCC6H4OCOCH3)2OH 2Al2O3 · B2O3 AlBr3 Al(C4H9O)3 Al(C4H9O)3 Al4C3 Al(ClO3)3 AlCl3

148.74 101.90 402.30 273.54 266.69 246.33 246.33 143.96 277.35 133.34

4.26 3.76

Al(C2H5O)3 AlF3 Al(OH)3 AlI3 Al(C3H7O)3 Al(CH3O)3 Al(NO3)3 · 9H2O AlN AlO3 Al(ClO4)3 · 6H2O Al(C6H5O)3 AlPO4 AlP Al(H2PO2)3

162.16 83.98 78.01 407.69 204.25 72.07 375.13 40.99 101.96 433.43 306.27 121.95 57.96 221.94

1050(50) subl 800 660.323 190– 193 anhyd ⬎280

Boiling point, ⬚C ca. 3200 2518 315

d aq; s acids s aq s HCl, H2SO4, alk i aq; v s alc; s bz, eth 14.3 g/100 mL aq; s glyc; i alc

1060 1740 ca. 1050 97.5

3.20518 0 0.967 1.02520 0 2.360

2100

subl 253 200– 20630mm subl 180 d ⬎2200400mm

2.44025

192.6

subl 181.1

1.14220 0 2.88225 4 2.42 3.9817 1.034620 0

140 1090 to Al2O3, 300 191.0 118.5 0 73 d 2517 2054(6) 120.8 d 265 ⬎1460 2550 d to PH3, 220

20514mm subl 1272

1.72 3.05 3.97 2.020 1.23 2.56 2.8515 4

Solubility in 100 parts solvent

382 13510mm 130 d 135 2980 anhyd 178

v sl s aq, alc, eth i aq d (viol) aq; s alc, acet, bz, CS2 FP 27; v s org solv v s org solv d aq; fire hazard v s aq; s alc g/100 mL: 70 aq (viol), 10012 abs alc; s CCl4, eth; sl s bz s hot aq d; v sl s alc, eth 0.56 aq; i a, alk, alc, acet i aq; s acids, alkalis d aq; s alc, eth, CS2 d aq; s alc, bz, chl, PE g/100 mL: 64 aq, 100 alc; s acet d aq, acid, alkali i aq; v sl s a, alk 133 g/100 mL20 aq d aq; s alc, chl, eth i aq; sl s a d aq i aq; s HCl, warm alkali

INTERACTIVE

Ac AcBr3 Al Al(C5H7O2)3 AlNH4(SO4)2 · 12H2O

Melting point, ⬚C

RIGHT

ethoxide fluoride hydroxide iodide isopropoxide methoxide nitrate 9-water nitride oxide (alpha-) perchlorate 6-water phenoxide phosphate phosphide phosphinate (hypophosphite)

Formula weight

(McGHP)

3.13

Actinium-227 bromide Aluminum acetylacetonate ammonium bis(sulfate) 12-water antimonide arsenide bis(acetylsalicylate) borate (2/1) bromide butoxide, secbutoxide, tertcarbide (4/3) chlorate chloride

Formula

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TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula

Formula weight

Density

Melting point, ⬚C

77.08

amidosulfate benzoate bromide

NH4SO3NH2 NH4C6H5O2 NH4Br

114.13 139.15 97.94

calcium arsenate 6-water carbamate carbonate 1-water chloride

NH4CaAsO4 · 6H2O NH4COONH2 (NH4)2CO3 · H2O NH4Cl

305.13 78.07 114.10 53.49

1.90515

1.527425

131 198 452 (subl under pressure) d 140 subl 60 volatilizes 60 237.8

chromate(VI) chromium(III) bissulfate 12-water copper(II) tetrachloride 2-water

(NH4)2CrO4 NH4Cr(SO4)2 · 12H2O

152.07 478.34

1.9112 1.72

d 185 94 d

(NH4)2CuCl4 · 2H2O

277.46

1.993

anhyd, 110

474.39

1.75720

⫺9H2O, 92

anhyd, 200

11.4 g/100 mL aq; v s glyc; i alc

Al(C3H7O)3 Al2Se3 Al2O3 · SiO2 AlNa(SO4)2 · 12H2O

204.25 290.84 162.05 458.28

1.057820 0 3.43720 4 3.247 1.67520

106 947

24814mm

d aq; s alc d aq, acid i aq; d HF; s fused alkali 110 g/100 mL15 aq; i alc

Al(C18H35O2)3 Al2(SO4)3 Al2(SO4)3 · 18H2O Al2S3 Al(BH4)3 Am NH3

877.41 342.15 666.46 150.16 71.53 243 17.03

1.070 1.61 1.6917 2.2013

117– 120 770 d d 86.5 1097 ⫺64.5 1176 ⫺77.75

61

12 lq: 0.6818 at bp g: 0.617515, 7.2atm 1.1720 114

1.260 2.429

subl 1500 44.5 2011 ⫺33.35 d d 160 subl 160 d 397 vacuo

i aq, alc; s bz, alk 36.4 g/100 mL20 aq; sl s alc 87 g/100 mL0 aq; i alc hyd aq; s acid d aq; ign air; expl in O2, 20 sa g/100 mL: 34 aq; 13.2 alc; s eth, organic solvents g/100 mL: 1484 aq, 7.915 MeOH; s alc v s aq; sl s alc g/100 mL: 2015 aq, 2.8 alc; s glyc 76 g/100 mL20 aq; v s acet, alc, eth

520

0.02 aq; s NH4Cl v s aq; sl s alc; i eth v s aq; i alc g/100 mL: 2615 aq, 0.619 abs alc; i acet, eth 34 g/100 mL20 aq; sl s MeOH 7.2 g/100 mL0 aq

d ⬎120

40.3 g/100 mL20 aq; s alc

INTERACTIVE

NH4C2H3O2

AlK(SO4)2 · 12H2O

LEFT

Ammonium acetate

Solubility in 100 parts solvent

(McGHP)

3.14

Aluminum (continued) potassium bis(sulfate) 12-water propoxide selenide silicon oxide (1/1) sodium bis(sulfate) 12-water stearate sulfate sulfate 18-water sulfide tetrahydridoborate Americium Ammonia

Boiling point, ⬚C

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44.06 252.07

1.10 2.155

d 36 d 180 to Cr2O3

dihydrogen arsenate dihydrogen phosphate disulfatocobatate(II) 6-water disulfatoferrate(II) 6-water disulfatoferrate(III) 12-water disulfatonickelate(II) 6-water dithiocarbamate diuranate(VI) fluoride formate heptamolybdate(VI)(6⫺) 4-water hexachloropalladate(IV) hexachloroplatinate(IV) hexadecanoate hexafluoroaluminate(3⫺) hexafluorogallate hexafluorogermanate hexafluorophosphate hexafluorosilicate hexanitratocerate(IV) hydrogen carbonate

NH4H2AsO4 NH4H2PO4 (NH4)2[Co(SO4)2 ] · 6H2O

158.97 115.03 395.23

2.311 1.80319 1.902

d 300 d 190

(NH4)2[Fe(SO4)2] · 6H2O NH4[Fe(SO4)2] · 12H2O

392.14 482.19

1.864 1.71

d 100 39– 41

(NH4)2[Ni(SO4)2] · 6H2O

395.00

1.923

NH4S(C⫽S)NH2 (NH4)2U2O7 NH4F NH4OOCH (NH4)2Mo7O24 · 4H2O

110.20 624.22 37.04 63.06 1235.86

(NH4)2[PdCl6] (NH4)2[PtCl6] NH4OOC(CH2)14CH3 (NH4)3[AlF6] (NH4)3GaF6 (NH4)2GeF6 NH4[PF6] (NH4)2[SiF6] (NH4)2[Ce(NO3)6] NH4HCO3

355.20 443.87 273.45 195.09 237.83 222.68 163.00 178.15 548.22 79.06

hydrogen citrate hydrogen difluoride hydrogen oxalate hydrate hydrogen phosphate hydrogen sulfate hydrogen sulfide

(NH4)2HC6H5O7 NH4HF2 NH4HC2O4 · H2O (NH4)2HPO4 NH4HSO4 NH4HS

226.19 57.04 125.08 132.06 115.11 51.11

1.48 1.51 1.556 1.619 1.78 1.17

hydrogen sulfite

NH4HSO3

99.11

2.03

36.4 g/100 mL20 aq; i alc 124 g/100 mL aq

1.00925 1.27 2.498

d to NH3 ⫹ HF 116 anhyd 90

2.418 3.065

d d 380 21– 22 d ⬎100 d 200 380 d 68 d

d 180 d 190

sl s aq 0.5 aq s aq; sl s bz; i alc, acet v s aq subl

107 (rapid heating) 240 d

d 350

s aq; i eth 74.8 g/100 mL20 aq; s alc, acet 18.6 g/100 mL20 aq; i alc, acet 135 g/100 mL20 aq; s alc, HNO g/100 mL: 17.420 aq, 10 glyc 100 g/100 mL aq; sl s alc v s aq; sl s alc s aq, alc; i bz, eth 69 g/100 mL20 aq; i alc, acet 100 g/100 mL aq; i alc, acet 128 g/100 mL0 aq; s glyc; i alc, acet

INTERACTIVE

124.6 anhyd, 170 d 155 146.9 d 25 to NH3 ⫹ H2S subl 150 in N2

v s aq; s alc; sl s eth v sl s aq, alk; s acids 100 g/100 mL0 aq; s alc 143 g/100 mL20 aq; s alc, eth 43 g/100 mL aq; s acids; i alc

RIGHT

99 d

1.586

d 230

8.95 g/100 mL20 aq

1.45120 4

1.78 2.10 2.564 2.18018 4 2.011

v s aq, alc 35.6 g/100 mL20 aq; s alc; flammable v s aq 37 g/100 mL20 aq; sl s alc; i acet 18 g/100 mL20 aq; v sl s alc

(McGHP)

NH4CN (NH4)2Cr2O7

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cyanide dichromate(VI)

267 g/100 mL10 aq

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Name

Formula

3.16

permanganate peroxodisulfate phosphinate phosphomolybdate hydrate picrate selenate(VI) stearate sulfamate sulfate sulfide sulfite hydrate (⫾)tartrate tetraborate 4-water

NH4MnO4 (NH4)2S2O8 NH4PH2O2 (NH4)3PO4 · 12MoO3 · H2O NH4C6H2N3O7 (NH4)2SeO4 NH4C18H35O2 NH4NH2SO3 (NH4)2SO4 (NH4)2S (NH4)2SO3 · H2O (NH4)2C4H4O6 (NH4)2B4O7 · 4H2O

167.12 35.05 83.03 192.94 144.94 107.11 289.36

3.309 2.51425 1.215 1.923

d 200 ⫺77 d d 150 subl 551 92 d

196.04 80.04

2.27625 4 1.72525

d 169.6

1.50

21– 22 d on standing d 70

1.95

d 240

136.97 228.20 83.04 1894.36

2.20810 1.982 1.634

explodes, 110 d 120 200 d

246.14 179.04 301.51 114.13 132.14 68.14 134.16 184.15 263.44

1.719 2.19320 4 0.89

d d 22 131 d ⬎280 d ⬇0 d 60 d

301.50 161.24 142.11 276.02 117.49

1.76920 1.41 1.601

Boiling point, ⬚C

220 vacuo

d 210

expl 180 d 240

expl 423

d 160

Solubility in 100 parts solvent

2.215 aq; i alc 49% dissolved NH3 v s aq; sl s alc; i acet 2.615 aq 167 g/100 mL20 aq; v s alc, acet v s aq, alc, glyc; i acet, eth 0.03820 aq s acids g/100 mL: 19220 aq; 3.820 alc; 1720 MeOH; s acet sl s aq; s alc; i acet v s aq, alc, acet; sl s eth 5.120 aq; s alc v s aq g/100 mL25: 21.9 aq, 1.49 EtOH, 0.014 BuOH, 0.029 EtOAc 0.815 aq 58 g/100 mL0 aq g/100 mL: 100 aq, 5 alc; i acet sl s aq 1.120 aq; sl s alc 117 g/100 mL7 aq; s HOAC; i alc sl s aq, bz; s alc; i acet v s aq; sl s alc 43.5 g/100 mL20 aq; i alc, acet v s aq; s alc, alk 75 g/100 mL20 aq; i alc, acet 58 g/100 mL15 aq; sl s alc s aq; i alc

INTERACTIVE

NH4OOC(CH2)16CH3 NH4OOC(CH2)6CH3 (NH4)2C2O4 · H2O (NH4)2TiO(C2O4)2 NH4ClO4

1.68

Melting point, ⬚C

LEFT

octadecanoate octanoate oxalate hydrate oxodioxalatotitanate(IV) perchlorate

Density

(McGHP)

Ammonium acetate (continued) hydrogen (⫾)tartrate NH4HC4H4O6 hydroxide NH4OH hypophosphite NH4H2PO2 iodate NH4IO3 iodide NH4I lactate NH4C3H5O3 magnesium arsenate NH4MgAsO4 · 6H2O 6-water molybdate(VI)(2⫺) (NH4)2MoO4 nitrate NH4NO3

Formula weight

top of page

short standard

base of DF

hydride (stibine) (III) iodide (III) oxide (valentinite) (V) oxide (III) selenide (III) sulfate (III) sulfide (V) sulfide (III) telluride triethyl trimethyl Argon Arsenic (III) bromide (III) chloride (di-) disulfide (III) fluoride (V) fluoride (III) hydride (arsine) (III) iodide (III) oxide (arsenolite)

SbH3 SbI3 Sb2O3 Sb2O3 Sb2Se3 SB2(SO4)3 Sb2S3 Sb2S5 Sb2Te3 Sb(C2H5)3 Sb(CH3)3 Ar As AsBr3 AsCl3 As2S2 AsF3 AsF5 AsH3 AsI3 As2O3

124.78 502.47 291.52 323.52 480.40 531.71 339.72 403.85 626.32 209.0 166.9 39.948(1) 74.92159(2) 314.63 181.28 213.97 131.92 169.91 77.95 455.63 197.84

5.475 g/L 4.92 5.7 3.78 5.81 3.62 4.56 4.120 6.52 1.32414 1.52315 1.7824 g/L0 5.72725 4 3.397225 4 2.149725 4 19 3.254 2.7315 15 7.46 g/L 3.420 g/L 4.73 3.86

304 d 140 d 150 d subl 149.6 d 150 d 200 630.7 ⬇680 96.6 73.4 3.5 292 8.3 ⫺91.5 168 655 ⫺O2, ⬎300 612 d 546 75 d 620 ⫺29 ⫺189.38 817 31.1 ⫺16.2 320 ⫺5.95 ⫺79.8 ⫺116.9 140.9 274

subl 341 d 170

1587 280 220.3 7922mm 376 141 ⫺18.4 401 1425

159.5 80.6 ⫺185.87 subl 615 220.0 130.2 565 57.8 ⫺52.8 ⫺62.5 424 460

s aq, eth v s aq; i abs alc s aq; i alc v s aq 25 g/100 mL16 aq 128 g/100 mL0 aq; v s alc; s acet 2.1515 aq; i alc, eth 0.4820 aq s hot conc H2SO4, aqua regia s acet, bz, chl 10 g/100 mL20 aq; s alc, bz, chl d aq; s HCl, chl, CCl4 444 g/100 mL20 aq d viol aq; s HOAc; forms solids with alc, bz, CS2, eth 20 mL/100 mL20 aq; s CS2, alc g/100 g25: 1.16 bz, 1.24 tol, 0.16 chl v sl s aq; s HCl, KOH v sl s aq; sl s warm KOH, eth v sl s aq; s conc HCl sl s aq 0.00220 aq (d); s H2SO4 i aq; s HCl (d), NaOH i aq; s HNO3 i aq sl s aq 3.36 mL/100 mL20 aq i aq; s HNO3 hyd aq; s HCl, CS2, PE misc chl, CCl4, eth; s HCl s alkali; v sl s bz s alc, bz, eth, HF hyd aq; s alc, bz, eth 28 mL/100 mL20 aq; s bz, chl s bz, tol; sl s aq, alc, eth 1.820 aq; s alc

INTERACTIVE

2.170 2.936 1.879 1.871 1.305 1.679 2.326 6.69725 6.0 4.35 3.1420 4 2.33620 4 4.37920 20 23 2.99

RIGHT

186.83 284.29 372.97 243.28 104.84 76.12 148.21 116.98 121.760(1) 196.68 361.47 228.12 299.02 178.75 216.75

(McGHP)

NH4[AlCl4] (NH4)2[PdCl4] (NH4)2[PtCl4] (NH4)2[ZnCl4] NH4[BF4] NH4SCN (NH4)2S2O3 NH4VO3 Sb SbAs SbBr3 SbCl3 SCl5 SbF3 SbF3

DEAN #37261

3.17

tetrachloroaluminate tetrachloropalladate(II) tetrachloroplatinate(II) tetrachlorozincate tetrafluoroborate thiocyanate thiosulfate vanadate(V)(1⫺) Antimony arsenide (III) bromide (III) chloride (V) chloride (III) fluoride (V) fluoride

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula weight

Density

Melting point, ⬚C

chlorate hydrate chloride

Ba(ClO3)2 · H2O BaCl2

322.24 208.24

3.179 3.85624

d 260 856 d 1300 to BaO ⫹ CO2 anhyd 120 962

chloride dihydrate chromate(VI) cyanide fluoride hexafluorosilicate hydrogen phosphate hydroxide 8-water iodate iodide manganate(VI)(2⫺) molybdate niobate nitrate nitrite hydrate

BaCl2 · 2H2O BaCrO4 Ba(CN)2 BaF2 Ba[SiF6] BaHPO4 Ba(OH)2 · 8H2O Ba(IO3)2 BaI2 BaMnO4 BaMoO4 Ba(NbO3)2 Ba(NO3)2 Ba(NO2)2 · H2O

244.26 253.33 189.36 175.32 279.40 233.31 315.48 487.13 391.14 256.26 297.27 419.14 261.34 247.35

3.097 4.49820

anhyd 113 d

4.89 4.2921 4 4.16515 2.1816 5.2320 5.15 4.85 4.975 5.44 3.2423 3.17330

1368 d 300 d 410 78 d 476 711

3.74 4.32 4.75 3.460 6.50 3.5120 2.19 3.9918 4.781 4.2865

313 315 260 310 subl 500 621 302 726.9 anhyd 110

1450 1455 592 d 115

460 d 800 707

1845 d 150

1835 ⫺O2, 250 1560

2260

2027

d

sl s aq; s dil acid, alk 66 g/100 mL20 aq; s alc s alkali, HNO3 i aq; s alk, slowly s hot HCl 0.0003 aq; s alkali, HNO3

d aq to Ba(OH) 58.8 g/100 mL0 aq; 0.014 alc s aq; sl s alc 0.9630 aq; s acet; i alc 92 g/100 mL0 aq; s MeOH, acet 0.0024 aq; s acids 34 g/100 mL20 aq; sl s alc, acet 36 g/100 mL20 aq; s MeOH; i acet, EtAc 31.7 g/100 mL0 aq 0.00120 aq; s mineral acids 80 g/100 mL14 aq; s alc 0.16120 aq; s acids 0.023525 aq; s NH4Cl soln; i alc 0.01 aq; s HCl, HNO3 3.920 aq 0.03320 aq; s HCl 169 g/100 mL20 aq; s alc, acet disprop to Ba(MnO4)2 ⫹ MnO2 0.005825 aq i aq 5.0 aq; v sl s alc, acet 54.8 g/100 mL0 aq; i alc

INTERACTIVE

197.84 229.84 386.72 246.04 310.17 532.64 210 137.33 273.43 451.70 411.14 297.14 197.34

Solubility in 100 parts solvent

LEFT

As2O3 As2O5 As2Se3 As2S3 As2S5 As2Te3 At Ba Ba(C2H3O2)2 · H2O Ba(O3SC6H5)2 Ba(BrO3)2 · H2O BaBr2 BaCO3

Boiling point, ⬚C

(McGHP)

3.18

Arsenic (continued) (III) oxide (claudetite) (V) oxide (III) selenide (III) sulfide (V) sulfide (III) telluride Astatine Barium acetate hydrate benzenesulfonate bromate hydrate bromide carbonate

Formula

top of page

short standard

base of DF

400 d 1973 505

perchlorate 3-water

Ba(ClO4)2 · 3H2O

390.27

2.74

d 400

Ba(MnO4)2 BaO2 BaSe Ba(C18H35O2)2 BaSO4 BaS BaSO3 Ba[Pt(CN)4] · 4H2O

375.20 169.33 216.29 704.28 233.39 169.39 217.39 508.54

3.77 4.96 5.02 1.145 4.5015 4.2515 4.44 2.076

d 200 450 d 1780 160 1580 2230 d

Ba(SCN)2 · 2H2O BaS2O3 · H2O BaTiO3 Ba3(VO4)2 BaZrO3 Bk Bk Be BeBr2 Be2C BeCl2 BeF2 BeH2 Be(OH)2 BeI2 Be(NO3)2 · 3H2O Be3N2 BeO BeSeO4 · 4H2O Be2SiO4 BeSO4 · 4H2O BeS

289.53 267.47 233.19 641.86 276.55 247 247 9.012 168.82 30.04 79.92 47.01 11.03 43.03 262.82 187.07 55.05 25.01 224.03 110.11 177.14 41.08

2.28618 3.518 6.02 5.14 5.52 14.78 13.25 1.847720 3.46525 1.9015 1.89925 1.986 0.65 1.909 4.32 1.557 2.71 3.025 2.03 3.0 1.713 2.36

permanganate peroxide selenide stearate sulfate sulfide sulfite tetracyanoplatinate(II)4-water thiocyanate 2-water thiosulfate hydrate titanate(IV)(2⫺) vanadate zirconate Berkelium (␣ form) (␤ form) Beryllium bromide carbide chloride fluoride hydride hydroxide iodide nitrate 3-water nitride oxide selenate 4-water silicate sulfate 4-water sulfide

d 160 d 220 1625 707 2500 1050 986 1287 508 d ⬎2127 415 (alpha) 555 ⫺H2, 220 93 480 60.5 2200 2578 (alpha) anhyd 300 1560 anhyd 270 d

3088

⫺O2, 800 d ⬎1600

i aq 3.520 aq; s acids, EtOH g/100 mL25: 129 aq, 78 EtOH, 42 BuOH, 81 EtOAc; i eth 198 g/100 mL25 aq; s MeOH; sl s acet v s aq 1.50 aq d aq i aq 0.00285 aq 7.920 aq; dec in acids 0.020 aq; i alc 2.86 aq; i alc 170 g/100 mL20 aq; s alc, acet 0.2120 aq; i alc, acet, eth, CS i aq i aq, alk; sl s acids

2467 521 482.3 subl 10361mm

487 d 125 3787 d 560 d 580

i aq; s acid, alk v s aq; s alc; 18.6 pyr d aq; s acids, alkali giving CH4 42 g/100 mL aq; s alc, eth, pyr, CS2 v s aq (slowly) d aq (slowly), acids (rapidly) s hot conc acids and alkali (viol) hyd aq violently; s alc, eth, CS2 166 g/100 mL20 aq d hot aq, alkali s conc H2SO4 49 g/100 mL25 aq i aq 39 g/100 mL20 aq; i alc i aq; s HNO3

INTERACTIVE

2.658 5.72 3.20

RIGHT

225.35 153.33 336.23

(McGHP)

BaC2O4 BaO Ba(ClO4)2

DEAN #37261

3.19

oxalate oxide perchlorate

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula weight

B2H6 B4H10 B5H9 B5H11 B6H10 B10H14 B3H6N3

27.67 53.32 63.13 65.14 74.95 122.22 80.50

B B4C BBr3

10.811 55.25 250.52

9.78 5.72 8.08215 4.75 7.7215 8.32 5.5525 9.303 g/L 4.96215 5.77820 4 7.922 2.83 8.76 5.10 6.32315 7.7020 4 5.08 6.78 7.74

Boiling point, ⬚C

Solubility in 100 parts solvent

271.5 218 d 233.5 d 727 154.4 ⫺67 ⫺water, 100 408.6 d red heat anhyd 80 817 d 150 d 710 d d 405 850 588.5

1564 453

1.214 g/L 2.340 g/L 0.60 0.745 0.67 0.948 lq: 0.81bp

⫺165.5 ⫺120 ⫺46.81 ⫺123 ⫺62.3 99.5 ⫺58

⫺92.5 18 60.0 63 108 d 213 55

FP ⫺68; s NH4OH, conc H2SO4 sl s aq; s bz hyd aq d aq d hot aq sl s aq; s bz, CS2, eth sl s aq (d)

2.34 2.51025 4 2.6

2076 2350 ⫺46.0

3864 ⬎3500 91.3

i aq s fused alkalis d aq, alc

447 900 subl 550 16.8 subl 439

1890

d

i aq; s hot H2SO4 d aq; s dil acids, acet i aq; s acids d aq; s HCl, alc, eth, acet i aq; s HCl i aq; s HF d (viol) aq giving O3 ⫹ BiF3 very unstable liquid d aq; s HCl i aq; s HCl, alc i aq; s HCl d aq; s HNO3, acet, glyc i aq; s HCl, HNO3 i aq; s KOH s conc HCl, HNO3 i aq; d aq reg d aq, alc; s HCl i aq, EtAc; s HNO3, HCl i aq; s alc

INTERACTIVE

208.9804 448.69 304.88 315.34 260.43 265.98 303.97 212.00 260.00 589.69 351.88 485.07 465.96 497.96 303.95 654.84 706.14 514.16 800.76

Melting point, ⬚C

LEFT

Bi BiBr3 BiBrO BiCl3 BiClO BiF3 BiF5 BiH3 Bi(OH)3 BiI3 BiIO Bi(NO3)3 · 5H2O Bi2O3 Bi2O5 BiPO4 Bi2Se3 Bi2(SO4)3 Bi2S3 Bi2Te3

Density

(McGHP)

3.20

Bismuth (III) bromide bromide oxide (III) chloride chloride oxide (III) fluoride (V) fluoride hydride (III) hydroxide (III) iodide iodide oxide (III) nitrate 5-water (III) oxide (V) oxide (III) phosphate (III) selenide (III) sulfate (III) sulfide (III) telluride Boranes diborane(6) tetraborane(10) pentaborane(9) pentaborane(11) hexaborane(10) decaborane(14) Borazine Boric acids, see under Hydrogen Boron carbide tribromide

Formula

top of page

short standard

base of DF

⫺107 ⫺127.1 ⫺60.4 2967 450.0 ⫺7.25 ⫺60.5 8.77 321 255 566 d 500 568 d 200 1110 ⫺H2O, 130 388 59.4 1540 700 1350 monohydrate, 80 1750 1041

12.7 ⫺100.4 125.7 594mm 2065 58.8 40.76 125.74 765 d 963 960 1748 CaO, 200 742

842 d ⬎160

1484

742 2300 d 825 to CaO d 825 to CaO anhyd 100 775 anhyd 200 100

1815

ca. 1940

d aq, alc 332 g/100 mL0 aq; s bz, chl, CCl4 d aq sl s hot acids 3.3 aq (slowly); s alc, glyc 3.4 g/100 mL20 aq; v s alc, chl, eth explodes with water; s HF d viol aq; d alk; smokes in air i aq, alk; s HNO3, hot HCl v s aq; s alc 99 g/100 mL20 aq; s acet; sl s eth s acids, NH4OH 120 g/100 mL25 aq 1.71 g/100 mL15 aq; sl s alc 4.3 g/100 mL25 aq 0.0002620 aq; s acids 84.7 g/100 mL20 aq; s alc, acet, eth 167 g/100 mL25 aq; s alc, acet i aq; s acids s dil acid i aq; d acids 94.4 g/100 mL25 aq; i alc, EtAc 0.1318 aq; s acids i aq; d HNO3 i aq, dil acids; s alkali CN’s d aq; s acids 37.4 g/100 mL0 aq; i alc, bz, acet 0.01325 aq 143 g/100 mL20 aq; v s alc, acet reacts with aq giving C2H2 s dil acids 0.0013 g/100 mL20; s acids 167 g/100 mL20 aq; s alc 42 g/100 mL20 aq; s alc, acet 74.5 g/100 mL20 aq; v s alc 167 g/100 mL aq; s alc

INTERACTIVE

5.141 g/L 3.077 g/LSTP 1.125 1.203 2.18 2.55 3.102325 4 2.460 2.80325 8.6525 2.341 5.192 4.2584 4.0525 2.226 6.33 4.79 5.670 2.455 8.15 cubic 5.96 5.8115 3.08 4.83 6.2015 4 8.0 1.55 1.50 3.620 3.38 2.222 2.83 2.711 2.711 2.1625 4 1.71 2.7125

RIGHT

117.17 67.81 141.94 131.89 24.82 69.62 159.808 174.90 136.90 112.411 230.50 272.22 172.42 183.32 164.44 150.41 146.43 366.22 308.48 128.41 399.18 191.37 769.56 144.48 240.01 360.25 40.078(4) 158.17 398.07 199.89 64.10 100.09 100.09 243.01 110.98 219.07 174.99

(McGHP)

BCl3 BF3 BF3 · O(C2H5)2 BF3 · HOCH3 BN B2O3 Br2 BF5 BF3 Cd Cd(C2H3O2)2 CdBr2 CdCO3 CdCl2 Cd(CN)2 CdF2 Cd(OH)2 CdI2 Cd(NO3)2 · 4H2O CdO Cd3P2 CdSe 3CdSO4 · 8H2O CdS CdTe CdWO4 Ca Ca(C2H3O2)2 Ca3(AsO4)2 CaBr2 CaC2 CaCO3 CaCO3 Ca(ClO3)2 · 2H2O CaCl2 CaCl2 · 6H2O Ca(ClO2)2

DEAN #37261

3.21

trichloride trifluoride trifluoride 1-diethyl ether trifluoride 1-methanol nitride oxide Bromine pentafluoride trifluoride Cadmium acetate bromide carbonate chloride cyanide fluoride hydroxide iodide nitrate 4-water oxide phosphide selenide sulfate-water (3/8) sulfide telluride tungstate(VI) Calcium acetate arsenate bromide carbide carbonate (aragonite) carbonate (calcite) chlorate 2-water chloride chloride 6-water chlorite

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula weight

Density

Melting point, ⬚C

2.50

2.37030 4 2.22018 4

anhyd 200 anhyd 120 ca. 1340 s ⬎350 d ⬎100 anhyd 100

Ca2P2O7

254.10

3.09

1353

CaF2 Ca(CHO2)2 Ca[OOC(CHOH)2CH4OH]2 Ca[C3H5(OH)3]PO4 Ca[SiF6] CaH2 Ca(OH)2 Ca(OCl)2 Ca(IO3)2 CaI2 Ca(C3H5O3)2 · 5H2O Ca[Mg(CO3)2] CaMoO4 Ca(NO3)2 Ca3N2 Ca(NO2)2 · 4H2O Ca(C18H33O2)2 CaC2O4 · H2O CaO Ca(C16H31O2)2 Ca[O2CH2CH2NHOCH(OH)C(CH3)2CH2OH]2

78.08 130.11 430.38 210.16 182.17 42.09 74.09 142.99 389.88 293.89 308.30 184.41 200.02 164.09 148.25 204.15 603.01 146.11 56.08 550.93 476.55

3.180 2.015

1418 300 d

2.29

subl

d 200

i aq; s HCl, HNO3 2533

d ⬎170 2.662 1.70 2.343 2.35 4.51915 4 3.956 2.872 4.35 2.504 2.67 1.674 2.2 3.34

1000 ⫺H2O, 580 100 d d ⬎540 783 ⫺3H2O, 100 d 730 56l 1195 d 83– 84 anhyd 200 2900 d ⬎155 d 195– 196

sl s aq; s dil acids 0.10 aq; i alc no known solv without dec s aq v s aq; i eth; d alc 1.830 aq

1755 anhyd 120

d ⬎400 3500

0.001520 aq; s conc mineral acids 16.6 g/100 mL20 aq; i alc 3.7220 aq 1.6620 aq; i alc i aq, acet d aq, alc 0.1710 aq; s acids d aq evolving Cl2; i alc 0.100 aq; i alc 68 g/100 mL20 aq; v s alc, acet; i eth 5.415 aq; v sl s alc 0.03218 aq; s HCl s conc mineral acids 152 g/100 mL30 aq d aq; s dilute acids (d) 84.5 g/100 mL18 aq; sl s alc 0.04 aq; s chl, bz; v sl s alc, eth 0.0006 aq; s acids 0.1325 aq; s acids 0.003 aq; sl s bz, chl, HOAc 36 g/100 mL aq; sl s alc, acet

INTERACTIVE

192.10 570.51 80.10 92.11 256.10 252.07

Solubility in 100 parts solvent

LEFT

CaCrO4 · 2H2O CaC6H6O7 · 4H2O CaCN2 Ca(CN)2 CaCr2O7 Ca(H2PO4)2 · H2O

Boiling point, ⬚C

(McGHP)

3.22

Calcium (continued) chromate(VI) 2-water citrate 4-water cyanamide cyanide dichromate(VI) dihydrogen phosphate hydrate diphosphate (pyrophosphate) fluoride formate (⫹)gluconate glycerophosphate hexafluorosilicate hydride hydroxide hypochlorite iodate iodide lactate 5-water magnesium carbonate molybdate(VI)(2⫺) nitrate nitride nitrite 4-water oleate oxalate hydrate oxide palmitate (⫹)panthothenate (vitamin B3)

Formula

top of page

short standard

base of DF

2.65

d 270

Ca(MnO4)2 · 5H2O CaO2 Ca(OC6H5)2 Ca3(PO4)2 Ca3P2 Ca(PH2O2)2 Ca(OOCC3H5)2 Ca(C7H5O3)2 · 2H2O CaSeO4 · 2H2O CaSe Ca2SiO4 Ca(C18H35O2)2 CaC4H6O4 · 3H2O CaSO4 CaSO4 · 0.5H2O CaSO4 · 2H2O CaS CaSO3 · 2H2O CaC4H4O6 · 4H2O CaTe CaB4O7 Ca[AlH4]2 Ca(SCN)2 · 3H2O Ca(-OOCCH2S-) · 3H2O CaS2O3 · 6H2O CaTiO3 CaWO4 Cf CfCl3 C C CO2

368.03 72.08 226.28 310.18 182.18 170.06 186.22 350.34 219.07 119.04 172.24 607.04 212.22 136.14 145.15 172.17 72.14 156.17 260.21 167.68 195.36 102.10 210.29 184.24 260.30 135.84 287.93 252.1 358.5 12.011

2.4 2.92 d in air 3.14 2.51

d explodes 275

CSe2 CS2

169.93 76.14

2.960 2.32 2.59

anhyd 200 anhyd 200

d 240 d 698

2130 179– 180 1460 anhyd 163 ⫺1.5 H2O, 128 2525 anhyd 100 anhyd 200

anhyd 163

i aq 0.00415 aq; s hot pyr; i acet, chl 1.2820 aq; s acids; i alc 0.20 aq; s acids 0.320 aq; s acids, glyc 0.2620 aq; s acid, glyc 0.02 (d) aq; d acids 0.004 aq; s acids d; sl s alc 0.004525 aq; s acids; sl s alc

4.873

1.872 3.98 6.06220

ign moist air d ⬎160 ⫺H2O, ⬎95 d ⬎45 1980

d ⬎220

s dil acids d viol aq, alc; i bz, eth 150 g/100 mL aq; v s alc s aq; v sl s alc, chl; i bz, eth 92 g/100 mL25 aq; i alc 0.0032 aq; d hot acids

900 5.88 3.513 2.267 c: 1.56⫺79 g: 1.975 g/L0 2.662625 4 1.2555

350063.5atm 3930 subl 3915– 4020 ⫺78.44 subl

88 mL/100 mL20 aq

⫺45.5 ⫺111.6

i aq; s acet, eth; misc CCl4; d alc FP ⫺30; 0.2920 aq; s alc, eth

125.1 46.56

INTERACTIVE

44.01

2.75 3.82 3.27

1670 ca. 1600 d ⬎300

g/100 mL25: 112 aq, 89.5 EtOH, 68 BuOH, 57 EtOAc, 43 acet 338 g/100 mL aq sl s aq; s acids sl s aq, alc 0.0325 aq; s HCl, HNO3; i alc d aq; s acids; i alc, eth 15.4 g/100 mL aq; sl s glyc s aq; sl s alc; i acet, bz 2.815 aq; 0.01516 EtOH 9.2 g/100 mL25 aq

RIGHT

diselenide disulfide

238.98

(McGHP)

3.23

permanganate 5-water peroxide phenoxide phosphate phosphide phosphinate propanoate salicylate 2-water selenate 2-water selenide silicate stearate succinate 3-water sulfate sulfate hemihydrate sulfate 2-water sulfide sulfite 2-water (⫾)tartrate 4-water telluride tetraborate tetrahydridoaluminate thiocyanate 3-water thioglycollate 3-water thiosulfate 6-water titanate tungstate(VI)(2⫺) Californium-252 chloride Carbon (diamond) (graphite) dioxide

Ca(ClO4)2

DEAN #37261

perchlorate

i aq, alc

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

suboxide

Formula weight

CH4 CO

16.04 28.01

C3O2

68.03

3.24

331.65 153.82 88.00 519.63 187.82 98.92 66.01

sulfide Cerium (III) bromide (III) chloride (III) fluoride (IV) fluoride (III) iodide (III) nitrate 3-water (IV) oxide (III) sulfate (IV) sulfate Cesium bromide carbonate chloride

COS Ce CeBr3 CeCl3 CeF3 CeF4 CeI3 Ce(NO3)3 3H2O CeO2 Ce2(SO4)3 Ce(SO4)2 Cs CsBr Cs2CO3 CsCl

60.07 140.11 379.83 246.47 197.11 216.11 520.83 380.17 172.11 568.42 332.24 132.9054 212.81 325.82 168.36

CsF CsOH

151.90 149.91

fluoride hydroxide

Boiling point, ⬚C

Solubility in 100 parts solvent

⫺182.48 ⫺205.05

⫺161.49 ⫺191.49

⫺111.3

6.8

s bz 2.3 mL/100 mL20 aq; 16 mL/100 ml alc; s HOAc, EtAc d aq to malonic acid; sl s CS2

90.1 ⫺22.9 ⫺183.6 171

190 76.7 ⫺127.8 subl 130 64.5 8.2 ⫺83.1

i aq; s alc, chl, eth 0.05 mL/100 mL aq; s alc, chl, eth sl s aq slowly hyd aq; s bz, chl, eth hyd aq hyd aq; s bz, HOAc hyd aq

⫺50.23 3440 1460 1730 2327

7.65 3.912 3.91 1.878515 4.44 4.24 3.99

⫺138.81 795 733 817 1430 d ⬎550 766 anhyd 150 2400 d 1000 d 195 28.44 636 792 646

4.115 3.68

703 272

1231 990

54 mL/100 mL20 aq; s alc, CS2 i aq; s acids s aq, alc s aq, alc i but slowly hyd aq; s H2SO4 i aq s aq 234 g/100 mL20 aq i aq; s acids 9.72 g/100 mL21 aq hyd aq; s dil H2SO4 d aq; s acids 107 g/100 mL18 aq; s alc; i acet v s aq; 11 g/100 mL20 alc; s eth g/100 mL: 18720 aq; 3425 MeOH; v s alc 322 g/100 mL18 aq 386 g/100 mL15 aq; s alc

0.415⫺164 lq: 0.814⫺195 g: 1.250 g/L0 1.11404 2.985 g/L 3.42 1.58925 25 1.96⫺184 4.3420 4 2.5 4.340 g/L lq: 1.139 g: 2.896 g/L 2.636 g/L 6.773 5.18 3.9725 6.157 4.77

⫺127.9 ⫺114.0

1400 d 200

668.2 ⬇1300 1300

INTERACTIVE

CBr4 CCl4 CF4 CI4 COBr2 COCl2 COF2

Melting point, ⬚C

LEFT

tetrabromide tetrachloride tetrafluoride tetraiodide Carbonyl bromide chloride fluoride

Density

(McGHP)

Carbon (continued) hydride (methane) monoxide

Formula

top of page

short standard

base of DF

408.77 361.87 70.905

dioxide fluoride heptoxide

ClO2 ClF Cl2O7

67.45 54.45 182.90

4.453 4.243 g: 2.9820 g/L lq: 1.5649⫺35 2.960 g/L 4.057 g/L 1.80525

monoxide pentafluoride trifluoride

Cl2O ClF5 ClF3

86.90 130.44 92.45

(ClO3)2 Cr Cr(C2H3O2)2 Cr(C2H3O2)3 CrBr2 CrBr3 CrCl2 CrCl3 CrF2 CrF3 Cr(CHO2)3 · 6H2O Cr(CO)6 Cr(OH)3 Cr(NO3)3 · 9H2O Cr2O3 CrO2 CrO3

166.90 51.996 170.09 229.13 211.80 291.71 122.90 158.35 89.99 108.99 295.15 220.06 101.02 400.15 151.99 84.00 99.99

3.25

trioxide (dimer) Chromium (II) acetate (III) acetate (II) bromide (III) bromide (II) chloride (III) chloride (II) fluoride (III) fluoride (III) formate 6-water hexacarbonyl (III) hydroxide (III) nitrate 9-water (III) oxide (IV) oxide (VI) oxide

3.813 g/L 5.724 g/L g: 4.057 g/L lq: 1.825 bp 20 1.9220 7.15 1.79 4.236 4.68 2.8825 2.87 3.79 3.8 1.77 1.80 5.21 4.89 2.7025

⬇1280 d 849

1005 ⫺101.5

⫺34.04

⫺59.6 ⫺155.6 ⫺91.5

10.9 ⫺100.1 82

⫺120.6 ⫺103 ⫺76.3

2.2 ⫺13.1 11.75

3.5 1907

⬇200 2679

842 814 1152 894 1400 d ⬎300 d 130 d 66 2330 197 198

subl 1300 d ⬎1300

explodes 210 d ⬎100 ⬇3000 ⫺O2, 250 d 250

2.625 aq 76.5 g/100 mL20 aq; s EtOH; i acet 23 g/100 mL20 aq; s acet; v sl s alc v s aq g/100 mL25: 1.96, 0.0086 EtOH, 0.118 acet, 0.0048 BuOH; i EtOAc, eth 244 g/100 mL12 aq 179 g/100 mL20 aq; i alc, acet, pyr 199 mL/100 mL25 aq 11.2 g/100 mL10 aq d viol aq; organics burst into flame hyd aq slowly; explodes on concussion or on contact with flame or I2 v s aq (forms HClO); s CCl4 hyd viol aq; organic matter and glass wool burst into flame reacts with aq s dil HCl sl s aq, alc; s a; i eth s aq s aq, alc s hot aq; v s alc v s aq s aq, alc (slow); i acet sl s aq; s hot HCl aq, alc; s HF, HCl s aq i aq, alc; s eth, chl i aq; s acids 208 g/100 mL15 aq; s alc i aq, alc; sl s acids, alkalis i aq; s HNO3 61.7 g/100 mL aq; may ign organics

INTERACTIVE

Cs2SeO4 Cs2SO4 Cl2

selenate sulfate Chlorine

565 621 414 490 250

RIGHT

4.93420 4.510 3.66 4.65 3.327

(McGHP)

307.81 259.81 194.91 281.81 232.36

DEAN #37261

CsIO3 CsI CsNO3 Cs2O CsClO4

iodate iodide nitrate oxide perchlorate

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

146.97 499.41

CrSO4 · 7H2O Cr2(SO4)3 · 18H2O CrO2Cl2 CrO2F2 Co Co(C2H3O2)2 · 4H2O Co(C2H3O2)3 CoBr2 CoCO3 CoCl2

274.17 716.45 154.90 121.99 58.9332 249.08 236.07 218.74 118.94 129.84

CoCl2 · 6H2O CoCrO4 Co(CN)2 CoF3 CoF3 Co(CHO2)2 · 2H2O Co(OH)2 Co(OH)3 CoI2 Co(NO3)3 · 6H2O CoC2O4 CoO Co3O4 Co3(PO4)2 · 8H2O CoSO4 · 7H2O CoS Co(SCN)2 · 3H2O

237.93 174.93 110.97 96.93 115.93 185.00 92.95 109.96 312.74 291.03 146.95 74.93 240.80 510.87 281.10 91.00 229.14

Melting point, ⬚C

4.6 1.82625

⬎1800 89

1.7 1.914525 4

d 100 ⫺96.5 31.6885mm 1494 anhyd 140 d ⬎100 678 (in N2) d 735

8.90 1.70519 4.90925 4 4.13 3.36725 4 1.924 ⬇4.0 1.87225 4 4.46 3.88 2.12922 4 3.37 4.46 5.58425 4 1.88 3.021 6.44 6.07 2.769 2.03 5.4518

anhyd 110 d d 300 1127 926 anhyd 140 168 (vacuo) ⫺H2O, 100 515 (vacuo) 55 d 250 ⫺s1935 d ⬎900 anhyd 200 anhyd 420 1180 anhyd 105

Boiling point, ⬚C

anhyd 400

117 subl 29.6 2927

1049

⬇1400 d 175 d 570 (vacuo) d ⬎74

d 1140

Solubility in 100 parts solvent

i aq, acids, aq reg 22 g/100 mL25 aq; i alc 22.9 g/100 mL0 aq; sl s alc 220 g/100 mL20 aq d aq; s bz, chl, eth, CCl4 i aq; s dil HNO3 s aq; 2.1 g/100 mL15 MeOH s aq, HOAc, alc 112 g/100 mL20 aq; s alc, acet 0.1815 aq; s hot acids 53 g/100 mL20 aq; s alc, acet, eth, glyc, pyr 97 g/100 mL20 aq i aq; s acids 0.004218 aq; s KCN 1.3620 aq; s warm mineral acids d aq 5.03 g/100 mL30 aq; i alc 0.00018 aq; v s acids 0.00032 aq; s acids 203 aq 155 g/100 mL30 aq; v s alc 0.00218 aq i aq; s acids, alkalis i aq; s acids, alkalis v sl s aq; s mineral acids 65 g/100 mL20 aq; sl s alc i aq; s acids 7.818 aq; s alc, eth

INTERACTIVE

CrPO4 CrK(SO4)2 · 12H2O

Density

LEFT

(II) chloride 6-water (II) chromate (II) cyanide (II) fluoride (III) fluoride (II) formate 2-water (II) hydroxide (III) hydroxide (II) iodide (alpha, black) (II) nitrate 6-water (II) oxalate (II) oxide (II,III) oxide (II) phosphate 8-water (II) sulfate 7-water (II) sulfide (II) thiocyanate 3-water

Formula weight

(McGHP)

3.26

Chromium (continued) (III) phosphate potassium bissulfate 12-water (II) sulfate 7-water (III) sulfate 18-water Chromyl chloride fluoride Cobalt (II) acetate 4-water (III) acetate (II) bromide (II) carbonate (II) chloride

Formula

top of page

short standard

base of DF

63.546 199.65 1013.80 149.17 143.45 223.35

8.9620 1.882

1084.62 115

2561.5 d 240

3.859 4.98 4.71

497 498

1345 900

4.0

d 200

Cu(ClO3)2 · 6H2O CuCl CuCl2 CuCl2 · 2H2O Cr2O3 · Cu2O

338.54 99.00 134.45 170.48 295.07

4.14 3.386 2.51 5.2420

65 430 300 d anhyd 200 d ⬎900

Cu2C6H4O7 · 2.5H2O CuCN CuF2 Cu(CHO2)2 Cu[SiF6] · 4H2O

360.22 89.56 101.54 153.58 277.60

2.92 4.23 1.831 2.56

Cu(OH)2 CuI Cu(NO3)2 · 3H2O Cu(OOCC17H33)2 CuC2O4 · 0.5H2O Cu2O CuO Cu(ClO4)2 Cu3(PO4)2 · 3H2O Cu(C7H5O3)2 · 4H2O CuSeO4 · 5H2O Cu2Se CuSe Cu(OOCC17H35)2 CuSO4 CuSO4 · 5H2O

97.56 190.45 241.60 626.46 160.57 143.09 79.54 262.45 434.63 409.83 296.58 206.05 142.51 630.50 159.61 249.69

3.368 5.67 2.32

6.025 4 6.31514 4 2.22523

2.559 6.8421 4 6.0 3.603 2.28416 4

anhyd 100 473 (in N2) 836

d 100 ⬇1400 d ⬎300

d 1676

d d 160 606 114.5 anhydr ⬎200 1235 1450 d ⬎130 d dehyd in air anhyd 265 1113 d 550 ⬇250 d ⬎560 anhyd 200

⬇1290 170 d d 310 ⫺O2, 1800

d ca. 480

242 g/100 mL18 aq; v s alc; s acet 0.024 aq; s conc HCl, conc NH4OH 73 g/100 mL20 aq; s alc, acet 76.4 g/100 mL25 aq; v s alc; s acet i aq; s HNO3 0.17 aq; s acids i aq; s NH4OH, KCN; d hot dil HCl 4.75 g/100 mL20 aq; s acids 12.5 aq 124 g/100 mL20 aq i aq; s acids i aq; s KCN, NH4OH, KI 138 g/100 mL0 aq; v s alc i aq; sl s alc; s eth 0.002 aq; s NH4OH i aq; s HCl i aq, alc; s acids, KCN 146 g/100 mL30 aq; s eth, EtAc; i bz i aq; s acids v s aq; s alc 25 g/100 mL20 aq; v sl s acet d HCl s acids i aq, alc, eth; s hot bz, pyr 14.3 g/100 mL0 aq; i alc 32 g/100 mL20 aq; s MeOH, glyc

INTERACTIVE

221.12

RIGHT

CuCO3 · Cu(OH)2

i; s HNO3, hot H2SO4 8 g/100 mL aq; 0.48 MeOH; sl s eth unstable in acids, bases; s NH4OH s a; i aq v sl s aq; s HCl, HBr, NH4OH 126 g/100 mL aq; s alc, acet, pyr; i bz i aq; s acids

(McGHP)

3.27

(II) carbonate hydroxide (1/1) (malachite) (II) chlorate 6-water (I) chloride (II) chloride (II) chloride 2-water (I) chromium(III) oxide (1/1) (II) citrate 2.5-water (I) cyanide (II) fluoride (II) formate (II) hexafluorosilicate 4-water (II) hydroxide (I) iodide (II) nitrate 3-water (II) oleate (II) oxalate hemihydrate (I) oxide (II) oxide (II) perchlorate (II) phosphate 3-water (II) salicylate 4-water (II) selenate 5-water (I) selenide (II) selenide (II) stearate (II) sulfate (II) sulfate 5-water

Cu Cu(C2H3O2) · H2O Cu(C2H3O2)2 · 3Cu(AsO2)2 Cu(BO2)2 CuBr CuBr2

DEAN #37261

Copper (II) acetate 1-water acetate meta-arsenate (1/3) (II) borate(1⫺) (I) bromide (II) bromide

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula

Formula weight

Density

(II) tungstate(VI)(2-) Curium-244 Cyanogen azide

CuWO4 · 2H2O Cm NC 9 CN NC 9 N3

347.41 244.063 52.03 68.04

13.51 2.335 g/L

bromide chloride fluoride Deuterium oxide Dysprosium bromide chloride fluoride oxide Einsteinium Erbium chloride oxide sulfate 8-water Europium (III) chloride (III) oxide (III) sulfate 8-water

NCBr NCCl NCF D2 or 2H2 D2O Dy DyBr3 DyCl3 DyF3 Dy2O3 Es Er ErCl3 Er2O3 Er2(SO4)3 · 8H2O Eu EuCl3 Eu2O3 Eu2(SO4)3 · 8H2O

105.92 61.47 45.02 4.03 20.03 162.50 402.21 268.86 219.50 373.00 252.083 167.26 273.62 382.52 766.83 151.965 258.32 351.93 736.24

2.005 2.697 g/L 1.975 g/L 0.169mp lq 1.105620 8.54025 4.78 3.67 7.465 7.8127 8.84 9.066 4.1 8.640 3.205 5.244 4.89 7.42 ⫺8H2O, 375

5.620 4 4.76 3.8315

1130

2.85

1084

d

1340 ⫺27.84

⬇3110 ⫺21.15

52 ⫺6.5 ⫺82 ⫺252.89 3.82 1412 880 680 1154 2408 860 1529 776 2418 anhyd 110 822 623 d 2350

61.5 13.8 ⫺46 ⫺249.49 101.43 2567 1480 1530 2230

2868 1500 d 630 1527

i aq; d HNO3, s KCN i aq; s hot HNO3, KCN sl s aq; s HCl 0.4220 aq; s acids, alkalis 0.00044 aq; s NH4OH, eth, alkali SCN 0.115 aq; d acids; s NH4OH s acids mL/100 mL: 45020 aq, 230 alc; s acetonitrile; pure azide detonates upon shock. Handle only in solvents. v s aq, alc, eth s aq, alc, eth sl s aq misc aq s acids s aq s aq i aq s aq s acid s aq; sl s alc 0.000525 aq; s acids 16.0 g/100 mL20 aq s acids s aq i aq; s acids 2.5620 aq

INTERACTIVE

159.16 95.61 225.16 265.66 121.62

Solubility in 100 parts solvent

LEFT

Cu2S CuS Cu2SO3 · H2O CuC4H4O6 · 3H2O CuSCN

Boiling point, ⬚C

(McGHP)

3.28

Copper (continued) (I) sulfide (II) sulfide (I) sulfite hydrate (II) tartrate 3-water (I) thiocyanate

Melting point, ⬚C

top of page

short standard

base of DF

nitrate

Fm F2 FONO2

257.0951 38.00 81.00

antimonide arsenide chloride fluoride nitrate phosphide selenide triethyl trimethyl Germanium (IV) bromide IV) chloride (IV) fluoride hydride (germane) (IV) oxide sulfide Gold (I) chloride (III) chloride (I) cyanide (III) cyanide 3-water

GaSb GaAs GaCl3 GaF3 Ga(NO3)3 GaP GaSe Ga(C2H5)3 Ga(CH3)3 Ge GeBr4 GeCl4 GeF4 GeH4 GeO2 GeS2 Au AuCl AuCl3 AuCN Au(CN)3 · 3H2O

191.48 144.65 176.08 126.72 255.74 100.70 148.68 146.90 114.84 72.61 392.23 214.42 148.60 76.64 104.61 136.74 196.967 232.42 303.33 222.99 329.07

⫺45.9

5.20 g/L

⫺167.3

⫺15.9

7.90 4.520 7.047 2.332 7.40715 3.01018 5.90429.6 (c) 6.09529.8 (lq) 5.614 5.31825 4 2.47 4.47

1312 ⬃609 1231 91 2340 anhyd 400 29.7646

3273 1580 2277

5.0325 1.05830 1.15115 5.323 3.132 1.879 6.521 g/L 3.363 g/L 4.25 3.01 19.3 7.57 4.7 7.1420 4

712 1238 77.9 ⬎1000 d 110 1465 960 ⫺82.3 ⫺15.7 937.3 26.1 ⫺49.5 ⫺15 ⫺164.8 1115 530 1064.18 289 d ⬎160 d d 50

d 500 2203

s acids s aq i aq s aq, alc s acids 4.08 aq s conc HCl, halogens, alkalis

201.2 subl 950 : Ga2O3, 200

s HCl s HCl d aq; s bz, CCl4, CS2 0.00425 aq; s HF v s aq

d 142.8 55.8 2830 186.4 86.5 d ⬎1000 ⫺88.1 1200

i aq; s hot H2SO4 hyd aq; s bz, eth hyd aq; s bz, eth; sl s dil HCl hyd aq; s dil HCl sl s hot HCl 0.4320 aq; s acids, alkalis

2856 subl 180

INTERACTIVE

118.45 223.02 157.25 263.61 214.25 451.36 362.50 746.81 69.723

⫺175

d aq viol; ignites organics and silicates hyd aq; s acet; ignites alc, eth; liquid explodes on slight concussion explodes on slightest provocation

RIGHT

FOClO3 Fr Gd GdCl3 GdF3 Gd(NO3)3 · 6H2O Gd2O3 Gd2(SO4)2 · 8H2O Ga

⫺188.13

(McGHP)

3.29

perchlorate Francium-223 Gadolinium chloride fluoride nitrate 6-water oxide sulfate 8-water Gallium

1527 ⫺219.61

1.513bp lq 1.667 g/L 1.507bp lq

DEAN #37261

Fermium-257 Fluorine

s aq reg, KCN, hot H2SO4 s HCl, HBr, KCN 68 g/100 mL20 aq; s EtOH s aq reg, KCN, NH4OH v s aq; sl s alc

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

3.30

440.47 253.96 441.93 526.24

AuSn Au2S3 Hf HfCl4 HfO2 He

315.66 490.13 178.49 320.30 210.49 4.00260

Ho HoBr3 HoCl3 H2N 9 NH2 H2N 9 NH2 · H2O H2N 9 NH3Cl ClH3N 9 NH3Cl H2N 9 NH3I H2N 9 NH3ClO4 (H3NNH3)SO4 (H2N 9 NH3)2C4H4O6 H2

164.9304 404.64 271.29 32.05 50.06 68.51 104.97 159.96 132.51 130.13 182.13 2.0159 0.07099bp (lq) 97.09 43.03 43.83 61.83 80.91

H2NSO3H HN3 HBO2 H3BO3 HBr

6.75 3.09

8.754 13.31 9.6820 0.176 g/L 0.1249 (lq) 8.79 4.86 3.7 1.003625 4 1.030 1.5 1.423

Melting point, ⬚C

460 subl 300 d 150 anhyd 160 418 d 197 2227 432 2774 ⫺272.1525atm

Boiling point, ⬚C

d 500 s HCl, KCN 50 g/100 mL aq; i alc

4450 subl 317 ⫺268.935 2720 1470 1510 113.5 118– 119 d 240 d 200

0.088 g/L

1474 914 718 2.0 ⫺51.7 & ⫺65 89 198 125 137 254 183 ⫺259.35

2.126 1.1260 2.486 1.43515 3.388 g/L20

205 ⫺80 236 171.0 ⫺86.87

d 37

1.93915 1.378

Solubility in 100 parts solvent

d 145 d ⫺252.88

d 357 ⫺66.71

i aq; s Na2S s HF hyd aq; s acet, MeOH i aq 0.861 mL/100 mL20 aq s acids; oxidizes in moist air s aq s aq FP 52; misc aq, alc misc aq, alc; i chl, eth v s aq; i org solv v s aq; sl s alc s aq d aq; s alc 3.420 aq; i alc 6.0 g/100 mL0 aq 1.9 mL aq

INTERACTIVE

amidosulfate (sulfamate) azide borate(1⫺) (cubic) borate(3⫺) (ortho) bromide

AuSb2 AuF3 Au2O3 AuNa3(S2O3)2 · 2H2O

Density

LEFT

Holmium bromide chloride Hydrazine hydrate Hydrazinium(1⫹) chloride (2⫹) chloride (1⫹) iodide (⫹1) perchlorate (2⫹) sulfate (1⫹) tartrate Hydrogen

Formula weight

(McGHP)

Gold (continued) diantimonide (III) fluoride (III) oxide (I) sodium thiosulfate 2-water stannide (III) sulfide Hafnium chloride oxide Helium

Formula

14.7 g/100 mL aq; sl s alc, acet v s aq; (very explosive) v sl s aq 5.56 g/100 mL30 aq 193 g/100 mL25 aq; misc alc

top of page

short standard

base of DF

81.91 240.90 84.46 36.46 37.47 116.52 43.03 27.03 3.02 162.01 177.98 20.01 21.02 87.81 99.99 100.07 180.11 175.91 127.91

70 0.922 g/L0

1.818 1.72625 4 1.463 4.62904 5.37 g/L20 1.70 3.12415 1.54920 lq 1.4120 1.000 1.104425 1.6720

1.4630 2.2– 2.5 1.86825 1.685

126 ⫺66.5 d

v s aq v s aq hyd aq

⫺114.18

⫺85.05 110 ⫺84.72 152 23.5 25.6 ⫺251.03 d

72 g/100 mL20 aq v s aq v s aq hyd viol : HCl ⫹ H2SO4 s aq d; s bz, eth misc aq

⫺114.64 ⫺80 ⫺86 ⫺13.4 ⫺256.56 d 100 61 ⫺83.57 ⫺83.6 d 130 ⫺80 ⫺87.3 19 110 :H5IO6 ⫺50.8 ⫺51.87 ⫺H O, 70 ⫺41.59 0.00 3.81 ⫺17.8 subl 110 122 ⫺0.43 d 60 subl 42.35 anhyd 150

19.52 120 18.65

165.5 220 :I2O5 ⫺35.1 127 ⫺35.7 83 120.5 100.00 101.42 203 d 138 d 130– 140 152 red heat d 213 H4P2O7, 200

aq 709 g/100 mL23 aq v s aq, alc; 2.54 g/100 g5 bz v s aq s aq v s aq s aq 60– 70% aq solution 269 g/100 mL20 aq; s alc; i eth 234 g/100 mL10 aq; misc alc v s aq v s aq 0.13318 aq; s alk vs misc aq misc aq v s aq (commercial 72% acid) 440 g/100 mL25 aq misc aq; s alc misc aq; s alc, eth v s aq slowly s aq : H3PO4; s alc v s aq : HPO3, ⬎300

INTERACTIVE

18.02 20.03 136.49 191.91 227.94 34.01 194.14 79.98 98.00

1.28220 4 1.526 g/L20 1.097 1.49 g/L25 1.753 1.140⫺4 20 0.687

⫺11 ⫺87.46 ⫺6 to ⫺8

RIGHT

128.91 179.97 63.02

1.49 3.39 g/L20

(McGHP)

48% HBr ⫹ H2O 2 HBr HOSO2Br HClO3 HCl 20.24% HCl ⫹ H2O 2 HCl HSO3Cl HOCN HCN 1 2 H H or HD (HO)2OP 9 PO(OH)2 H4P2O7 HF 35.35% HF ⫹ H2O 2 HF H[BF4] H2PO3F HOSO2F H2[SiF6] · 2H2O HIO3 HI 57% HI ⫹ H2O HI H2MoO4 · H2O HNO3 69% HNO3 ⫹ H2O H2O D2O or 2H2O HClO4 · 2H2O HIO4 H5IO6 H2O2 HO3S 9 O 9 OSO3H HPO3 H3PO4

DEAN #37261

3.31

bromide (constant boiling) bromide-d bromosulfate chlorate (40% solution) chloride chloride (constant boiling) chloride-d chlorosulfate cyanate cyanide deuteride diphosphate(IV) diphosphate(V) fluoride fluoride (constant boiling) fluoride-d fluoroborate fluorophosphate fluorosulfate hexafluorosilicate 2-water iodate iodide iodide (constant boiling) iodide-d molybdate hydrate nitrate nitrate (constant boiling) oxide (water) oxide-d2 perchlorate 2-water periodate(1⫺) (meta) periodate(5⫺) peroxide peroxodisulfate phosphate(V)(1⫺) (meta) phosphate(V)(3⫺) (ortho) commercial 85% acid

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula

(HONH3)2SO4 In InSb InAs InCl3 InF3 In2O3 InP In2Te3 In(CH3)3 I2

Boiling point, ⬚C

Solubility in 100 parts solvent

H3PO4

101.03

1.90825

46.0

HPH2O2 H2PHO3

66.0 82.00

1.49319 1.65125 4

26.5 ⬇73

d 50 d ⬎180

s aq v s aq, alc

144.98 80.98 98.08 100.09 34.08 177.63 229.66 129.62 110.21 249.86 33.03 69.49

2.950815 4 2.12⫺4 bp 1.831820 1.8620 1.5392 g/L0 3.0 3.068 5.687 g/L 1.48320 4 5.5 1.20440 4 1.68020

58 ⫺65.73 10.38 14.35 ⫺85.49 d to TeO2 ⫺2H2O, 120 ⫺49 ⫺26.9 anhyd 100 33 150.5

260 ⫺41.4 335.5

164.14 114.82 236.58 189.74 221.18 171.82 277.63 145.79 612.44 159.93 253.809

7.31 5.77 5.67 4.0 4.39 7.179 4.81 5.75 1.568 4.6325

vs aq (viol) 9.5 mL/100 mL20 aq; s CS2 misc aq misc aq 0.334 mL25 aq 0.0007 aq; s acid, alkali 30 g/100 mL18 aq s aq d d aq, alc i aq; s HF, alkalis v s aq, MeOH; sl s bz, eth g/100 mL: 8317 aq, 12.520 MeOH, 5.120 EtOH; s glyc 69 g/100 mL20 aq s acids i aq

2

170 156.60 525 942 583 1170

v s aq

⫺60.33 320 : TeO ⫺2 57.8 5822mm d

2072

subl 500 850

1062 667 88.4 113.60

135.8 185.24

212 g/100 mL25 aq 0.04025 aq; s dilute acids s hot mineral acids v sl s acids

INTERACTIVE

sulfate Indium antimonide arsenide chloride fluoride oxide phosphide telluride trimethyl Iodine

Melting point, ⬚C

LEFT

H2SeO4 H2Se H2SO4 2 H2SO4 or D2SO4 H2S H2TeO3 H6TeO6 H2Te (HS)2CS H2WO4 HONH2 HONH3Cl

Density

(McGHP)

3.32

Hydrogen (continued) phosphate(V)(3⫺)-d3 phosphide, see Phosphine phosphinate phosphonate (phosphorous acid) selenate selenide sulfate sulfate-d2 sulfide tellurate(IV) tellurate(VI) (monoclinic) telluride trithiocarbonate tungstate(VI)(2⫺) Hydroxylamine Hydroxylammonium chloride

Formula weight

d aq; s acet, bz g/100 mL25: 0.029 aq, 14.1 bz, 16.5 CS2, 21.4 EtOH, 25.2 eth, 2.6 CCl4; s chl, HOAc

top of page

short standard

base of DF

hexafluoride (III) oxide

IrF6 Ir2O3

306.21 432.43

4.82

IrO2 IrCl3 Fe FeAsO4 · 2H2O FeBr2 FeBr3 Fe3C FeCO3 FeCl2 FeCl3 FeS2 FeF2 FeF3 Fe4[Fe(CN)6]3 Fe(OH)2 FeO(OH) FeI2 Fe(NO3)3 · 9H2O Fe2N FeC2O4 · 2H2O FeO Fe3O4 Fe2O3 Fe(CO)5 Fe3(PO4)2 · 8H2O Fe2P

224.22 298.58 55.845 230.79 126.75 295.67 179.55 115.85 126.75 162.20 119.98 93.84 112.84 859.23 89.86 88.85 309.65 404.00 125.70 179.89 71.84 231.53 159.69 195.90 501.60 142.66

11.7 5.30 7.86 3.18 3.16 4.5 7.694 3.9 3.16 2.898 5.02 4.09 3.87 1.80 3.4 4.26 5.315 1.684 6.35 2.28 6.0 5.17 5.25 1.49 2.58 6.85

(IV) oxide trichloride Iron (III) arsenate 2-water (II) bromide (III) bromide (tri-) carbide (II) carbonate (II) chloride (III) chloride disulfide (pyrite) (II) fluoride (III) fluoride (III) hexacyanoferrate(II) (II) hydroxide (III) hydroxide oxide (II) iodide (III) nitrate 9-water (di-) nitride (II) oxalate 2-water (II) oxide (II,III) oxide (III) oxide pentacarbonyl (II) phosphate 8-water phosphide

6.45 40 27.2 ␣-form 9.43 d 275 ⬃33 2447

4.77 subl 116 d 97 d 100.5

44.4 d ⬃ 1000 to Ir ⫹ O2 d 1100 d 763 1535 1020 677 d 1227 d 677 304 d 602 1100 subl 1000 250 d

53.6

anhyd 136 587 47 d 200 d 150 1377 1597 1565 ⫺20.0 1370

64 subl ⬃2550

2861 1023

1024 ⬇316 1837

1093 d 100

d 3414

103.9

s aq (d), s NaOH s aq, alc, eth, CS2 d aq; s alc, eth, HOAc d aq viol 187 g/100 mL13 aq d aq; s alc, bz, HCl s K2SO4 fusion, KOH ⫹ KNO3 fusion d aq s boiling HCl 0.000220 aq; s HCl i acids, alkalis i aq; s acids v sl s aq; s acids 117 g/100 mL20 aq; v s alc s aq, alc, eth, HOAc s acids 0.07218 aq; s acids 62.5 g/100 mL20 aq; v s alc, acet 74 g/100 mL0 aq; s alc, acet, eth s acids d sl s aq; s dil HF; i alc, bz, eth 0.09125 aq; s HF i aq; s HCl 0.006 aq; s acids i aq, alc; s HCl s aq 138 g/100 mL20 aq s HCl 0.04418 aq; s mineral acids i aq; s acids i aq; s acids i aq; s HCl FP ⫺20; i aq; s alc, bz, eth i aq; s acids s hot mineral acids

INTERACTIVE

lq: 2.86 4.416 3.1029 4 3.1925 4.98 3.202⫺4 22.6520 4

RIGHT

259.89 206.81 162.36 221.90 333.81 233.26 192.217

(McGHP)

IF7 IBr ICl IF5 I2O5 ICl3 Ir

DEAN #37261

3.33

heptafluoride monobromide monochloride pentafluoride pentoxide trichloride Iridium

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula

Formula weight

Density

Melting point, ⬚C

6.78 3.5 4.30 1.89 3.09718 4.7

d 1140 1220 anhyd 300 d 1178 1190

3.7493 g/L 3.24 6.162 3.84

fluoride nitrate 6-water oxide sulfate sulfate 9-water Lawrencium Lead (II) acetate 3-water (IV) acetate (II) azide

LaF3 La(NO3)3 · 6H2O La2O3 La2(SO4)3 La2(SO4)3 · 9H2O Lr Pb Pb(C2H3O2)2 · 3H2O Pb(C2H3O2)4 Pb(N3)2

195.90 433.01 325.81 566.00 728.14 262 207.2 427.3 443.4 291.2

5.9

11.3420 4 (fcc) 2.55 2.228 4.7

Pb(BO2)2 · H2O PbBr2 PbCO3 Pb(ClO3)2 PbCl2 PbClF

310.8 367.0 267.2 374.1 278.1 261.7

5.598 anhyd 6.69 6.61 3.89 5.98 7.05

⫺157.36 subl⫺60 920 852 anhyd 852 (in HCl atm) 1493 40 2305 d white heat anhyd 400 1627 327.43 75 ⬇75– 180 expl 350 or when shocked anhyd 160 371 d 340 : PbO d 230 501

(II) borate(1⫺) hydrate (II) bromide (II) carbonate (II) chlorate (II) chloride (II) chloride fluoride

6.51 3.60 2.821

s HCl

d 671 d ⫺153.22 3464 1812

2327 d 126 4200

d HCl 48 g/100 mL20 aq slowly s aq (hyd); sl s alc 0.000618 aq; s acid v s aq 5.94 mL/100 mL20 aq s anhyd HF i aq; s HCl v s aq v s aq; s alc

181 g/100 mL20 aq; v s alc s acids 2.33 g/100 mL20 aq; i alc 2.92 g/100 mL20 aq; i alc

1749 d ⬎200

s hot conc HNO3, HCl, H2SO4 g/100 mL: 6315 aq, 3.3 alc s hot HOAc, bz, chl, conc HX acids 0.02318 aq; v s HOAc

mp 500 912

s acids 0.4500 aq; s acids; i alc i aq; s acids, alkalis 140 g/100 mL18 aq; v s alc 0.9920 aq

950

INTERACTIVE

134.81 131.93 203.77 278.01 399.88 87.92 230.09 83.80 121.80 138.9055 245.26 371.37

LEFT

FeSe FeSiO3 Fe2SiO4 FeSO4 · 7H2O Fe2(SO4)3 FeS Fe(SCN)3 Kr KrF2 La LaCl3 LaCl3 · 7H2O

Solubility in 100 parts solvent

(McGHP)

3.34

Iron (continued) (II) selenide (II) silicate(2⫺) (II) silicate(4⫺) (II) sulfate 7-water (III) sulfate (II) sulfide (III) thiocyanate Krypton difluoride Lanthanum chloride chloride 7-water

Boiling point, ⬚C

top of page

short standard

base of DF

Pb(OH)2 PbI2 PbMoO Pb(NO3)2 Pb(C18H33O2)2 PbC2O4 PbO PbO2 Pb3O4 Pb3(PO4)2 PbSe PbSiO3 Pb2SiO4 Pb(C18H35O2)2 PbSO4 PbS PbTe Pb(C2H5)4 Pb(CH3)4 Pb(SCN)2 Li LiC2H3O2 · 2H2O LiAlO2 LiNH2 LiC7H5O2 LiBO2 Li[BH4] LiBrO3 LiBr Li2CO3

241.2 461.0 367.1 331.2 770.1 295.2 223.2 239.2 685.6 811.5 286.2 283.3 506.5 774.2 303.3 239.3 334.8 323.45 267.35 323.4 6.941 102.02 65.92 22.96 128.06 49.75 21.78 134.85 86.84 73.89

7.59 6.16 6.7 4.53 5.28 9.35 (red) 9.64 8.92 7.0 8.15 6.5 7.60 1.4 6.29 7.60 8.16 1.653 1.995 3.82 0.53420 1.3 2.554 1.178 2.18 0.66 3.62 3.464 2.11

844 830 ⬇ 600 d 190 d 280 to Pb2As2O7 d 145 410 1065 470 d 300 886 d 290, Pb3O4 d 595 : PbO 1014 1078 764 743 ⬇125 1170 1118 924 ⫺137 ⫺30.2 d 190 180.54 58 1700 380 ⬎300 849 268 552 720

d 1297

872

1472 d d 595, PbO

1300 subl ⬇200 110 1341 d d 450 vacuo 1719 d 380 1289 d 1300

i aq; s dil HNO3, alkalis 0.06420 aq hyd aq 1.6 g/100 mL20 aq s HNO3, alkalis 0.01620 aq; s acids, alkalis 0.06320 aq; s KI, Na2S2O3, alkalis s acids, alkalis g/100 mL: 5620 aq, 1.3 MeOH s alc, bz, eth s acids, alkalis 0.001720 aq; s HNO3 s HCl, dil HNO3 ⫹ H2O23, H2C2O4 s HNO3, hot HCl s HNO3, alkalis s HNO3 s acids 0.0535 aq; s hot alc 0.00425 aq; s NaOH 0.000618 aq; s HNO3, hot dil HCl i acids and alkalis i aq; s bz, hydrocarbons s hydrocarbons 0.4418 aq, s HNO3, NaOH d aq to LiOH 63 g/100 mL20 aq; v s alc d aq (: LiOH ⫹ NH3); i bz, eth g/100 mL: 33 aq; 7.7 alc 2.7 g/100 mL20 aq; i alc s aq, eth, THF, aliphatic amines 179 g/100 mL20 aq 164 g/100 mL aq; s alc, eth 1.3 g/100 mL20 aq; i alc; s acids

INTERACTIVE

6.12 8.445 6.7 4.63 5.94

RIGHT

323.2 245.2 283.2 297.2 347.1

(McGHP)

3.35

(II) hydroxide (II) iodide (II) molybdate(VI)(2⫺) (II) nitrate (II) oleate (II) oxalate (II) oxide (litharge) (IV) oxide (II,IV) oxide (red lead) (II) phosphate (II) selenide (II) silicate(2⫺) (II) silicate(4⫺) (II) stearate (II) sulfate (II) sulfide (II) telluride tetraethyl tetramethyl (II) thiocyanate Lithium acetate 2-water aluminate(1⫺) amide benzoate borate(1⫺) borohydride bromate bromide carbonate

PbCrO4 PbF2 PbF4 Pb(CHO2)2 PbHAsO4

DEAN #37261

(II) chromate(VI)(2⫺) (II) fluoride (IV) fluoride (II) formate (II) hydrogen arsenate

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

2.07 2.15

Melting point, ⬚C

1681 d 950

no solvent known; flammable

1626

12.4 g/100 mL20 aq; sl s alc 66 g/100 mL aq; in alc 165 g/100 mL20 aq & alc; v s acet 50 g/100 mL20 aq; s alc d aq forms LiOH in aq 47.4 g/100 mL25 aq; v s organic solv

42.39 165.91 281.98 25.94 161.79 7.95 8.96 23.95 181.84 133.84 68.95 34.83 29.88 106.39

Li2O2 Li2SiO3 Li2SO4 Li2B4O7 Li[AlH4]

45.88 89.97 109.95 169.12 37.95

2.31 2.5225 4 2.22 0.917

d ⬎195 to Li2O 1201 859 917 d 137

LiBH4 Lu LuCl3 Lu2(SO4)3 · 8H2O Mg Mg(C2H3O2)2 MgAl2O4 Mg(NH2)2 Mg(BO2)2 · 8H2O MgBr2

21.79 174.967 281.33 782.25 24.305 142.00 142.25 56.35 254.04 184.11

0.666 9.841 3.98

268 1663 892

d 380 3402 subl ⬎750

1.73820 1.42 3.6 1.3925 4 2.30 3.722

651 323 d 2135 ign in air

1100

711 d

1158

0.76– 0.77 0.881 1.45 4.502 4.061 2.38 1.27 2.013 2.43

Solubility in 100 parts solvent

77 g/100 mL20 aq; s alc, acet 142 g/100 mL18 aq; s EtOH 61 g/100 mL15 aq; sl s alc 0.1325 aq; s acids

LiCl Li2CrO4 · 2H2O Li3C6H5O7 · 4H2O LiF Li3[AlF6] LiH Li2H or LiD LiOH LiIO3 LiI LiNO3 Li3N Li2O LiClO4

2.640

613 anhyd 75 anhyd 105 848 1012 680 686 471.2 450 469 ⬃255 813 1570 236

Boiling point, ⬚C

1360

1174

2563 d ⬃ 400 LiCl ⫹ O2

d dil HCl 34.5 g/100 mL20 aq; i alc sl s aq d aq, alc; g/100 mL: 30 eth, 13 THF; flammable s aq pH ⬎7; s eth, THF s acids s aq 42.3 g/100 mL20 aq i aq; s dilute acids 53.4 g/100 mL20 aq; v s alc v sl s HCl d viol water giving NH3 sl s aq; s acids 101 g/100 mL20 aq

INTERACTIVE

tetrahydridoborate Lutetium chloride sulfate 8-water Magnesium acetate aluminate(2⫺) amide borate(1⫺) 8-water bromide

Density

LEFT

peroxide silicate(2⫺) sulfate tetraborate(2⫺) tetrahydridoaluminate

Formula weight

(McGHP)

3.36

Lithium (continued) chloride chromate(VI)(2⫺) 2-water citrate 4-water fluoride hexafluoroaluminate(3⫺) hydride hydride-d hydroxide iodate iodide nitrate nitride oxide perchlorate

Formula

top of page

short standard

base of DF

84.31 95.21 62.30 121.22 274.47 26.32 174.33

3.05 2.33 3.148 3.09 1.788 1.45 2.1315

990 714 1263 1115 ⫺SiF4, 120 d 200 vacuo anhyd 205

1412 2270

0.01 aq; s acids 54.6 g/100 mL20 aq 0.01325 aq; s HNO3

ign in air d 550

51 g/100 mL20 aq; i alc d aq and alc violently sl s aq; s acids

Mg(OH)2 MgI2 MgC6H10O6 · 3H2O MgC16H14O6 Mg(NO3)2 · 6H2O Mg3N2 Mg(C18H33O2)2 MgO Mg(ClO4)2

58.32 278.12 256.51 326.59 256.41 100.93 587.22 40.30 223.21

2.36 4.43

350 d 634

0

1.464 2.712

95 d 270

d 129

3.65– 3.75 2.21

2800 d ⬎251

3600

⬇3.0 1.6415 3.19225 4 3.21 2.0 3.60 1.67 1.725 6.89 7.2120 1.589 4.39 6.89 3.125 2.977 2.01 1.75

d 100 anhyd ⬃400 d 1557 1898 1100 778 anhyd 250 anhyd 200 1244 fctetr 80 698 1520 d ⬎200 650 97.5 d 110

mp: 2227 2095 1027

1210 anhyd 198

INTERACTIVE

262.19 56.30 268.09 352.96 100.39 140.69 76.70 167.32 246.47 212.46 272.14 54.9380 245.09 214.75 176.83 114.95 125.84 187.91 389.98

0.00125 aq; s acids 140 g/100 mL20 aq; s alc 4 g/100 mL aq; sl s alc 0.004100 aq; i alc 120 g/100 mL20 aq; v s alc d aq; s acids sl s alc, eth, PE i aq, alc; s acids g/100 mL25: 73 aq, 18 EtOH, 44.6 BuOH, 54 EtOAc, 32 acet v s aq s acids sl s aq d; s dilute acids 0.02 aq; s acids i aq; v sl s HF i aq; d hot HCl d aq, HCl s aq, HCl 27.2 g/100 mL aq; sl s alc 0.6625 aq i aq; d acids d aq; s acids 38 g/100 mL50 aq; v s alc 147 g/100 mL20 aq; s alc d aq; s acid 0.006525 aq; s acids 74 g/100 mL20 aq; s alc, pyr; i eth 143 g/100 mL aq; s alc; i eth i aq; s organic solvents

RIGHT

Mg(MnO4)2 MgO2 Mg(BO3)2 · 7H2O Mg3(PO4)2 · 5H2O MgSiO3 Mg2SiO4 Mg2Si Mg2Sn MgSO4 · 7H2O MgSO3 · 6H2O MgWO4 Mn Mn(C2H3O2)2 · 4H2O MnBr2 Mn3C MnCO3 MnCl2 MnCl2 · 4H2O Mn2(CO)10

(McGHP)

3.37

permanganate peroxide peroxoborate 7-water phosphate 5-water silicate(2⫺) silicate(4⫺) (di-) silicide (di-) stannide sulfate 7-water sulfite 6-water tungstate(VI)(2⫺) Manganese acetate 4-water bromide (tri-) carbide carbonate chloride chloride 4-water decacarbonyl

MgCO3 MgCl2 MgF2 Mg2Ge Mg[SiF6] · 6H2O MgH2 MgHPO4 · 3H2O

DEAN #37261

carbonate chloride fluoride (di-) germanide hexafluorosilicate 6-water hydride hydrogen phosphate 3-water hydroxide iodide lactate 3-water mandelate nitrate nitride oleate oxide perchlorate

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula weight

(I) chloride

Hg2Cl2

(II) chloride

3.707 3.98 3.54 3.258 5.04 1.8 5.37 4.89 5.08 4.84 2.396

7.307 6.05

1196 930 d ⬎600 d 638 25.8 1840 877 d ⫺O2, 530 1567 ca. ⫺20 d to PH3 1290 700 anhyd 400– 450 anhyd 280 1610 1360 ⫺38.83 178– 180 d 165 subl 393 d 237

472.09

7.16

subl 382

HgCl2

271.50

5.4

277

(II) cyanide

Hg(CN)2

252.63

4.00

d 320

(I) fluoride

Hg2F2

439.18

8.73

⬎570 d

3.48 3.25 2.95 2.09 3.99 4.54 13.534 3.28

Boiling point, ⬚C

1820

1017

ca. 25

d 850

356.7

322 subl d without melting 304

Solubility in 100 parts solvent

i aq; s acid 0.6640 aq; s HF, conc HCl hyd aq; s acid 0.00218 aq; s acids s aq v s aq, alc i aq; s acids i aq; s HCl giving off Cl2 s HCl; i HNO3, cold H2SO4 i aq; s HCl explodes 85; v s aq 15 g/100 mL aq; i alc i aq, HCl 52 g/100 mL aq; i alc 70 g/100 mL20 aq 115 g/100 mL20 aq 0.000618 aq; s acids i aq; s HNO3, hot conc H2SO4 g/100 mL: 4010 aq, 7.515 MeOH v s NaCl soln; sl s alc i aq, alc, eth; d hot HCl g/100 mL: 0.5620 aq; 2025 alc; v s HCl, HBr s aqua regia; i aq, alc, eth

INTERACTIVE

283.82 92.93 111.93 88.95 308.75 287.04 70.94 157.87 86.94 228.81 221.87 202.93 131.02 151.00 169.02 277.11 87.00 150.84 200.59 318.68 424.83 560.99 360.40

Melting point, ⬚C

LEFT

Mn2P2O7 MnF2 MnF3 Mn(OH)2 MnI2 Mn(NO3)2 · 6H2O MnO Mn2O3 MnO2 Mn3O4 Mn2O7 Mn(PH2O2)2 · H2O MnSiO3 MnSO4 MnSO4 · H2O MnSO4 · 7H2O MnS Mn2TiO4 Hg Hg(C2H3O2)2 Hg(C7H5O2)2 Hg2Br2 HgBr2

Density

(McGHP)

3.38

Manganese (continued) diphosphate (II) fluoride (III) fluoride hydroxide iodide nitrate 6-water (II) oxide (III) oxide (IV) oxide (II,IV) oxide (VII) oxide phosphinate hydrate silicate, metasulfate sulfate hydrate sulfate 7-water sulfide titanate(IV)(2⫺) Mercury (II) acetate (II) benzoate (I) bromide (II) bromide

Formula

g/100 mL20: 7.15 aq, 26 alc, 4 eth 8.3 glyc, 0.5 bz; s HOAc, EtAc g/100 mL20: 9.3 aq, 25 MeOH, 8 EtOH hydrolyses in water

top of page

short standard

base of DF

(I) nitrate 2-water (II) nitrate (I) oxide (II) oxide

Hg2(NO3)2 · 2H2O Hg(NO3)2 Hg2O HgO

561.22 324.60 417.18 216.59

4.79 4.3 9.8 11.14

(I) sulfate (II) sulfate (II) sulfide (cinnabar)

Hg2SO4 HgSO4 HgS

497.24 296.65 232.66

7.56 6.47 8.17

Hg(SCN)2 Mo MoBr3 MoCl4 MoCl5 MoF6 Mo(CO)6 MoO2 MoO3 Mo2S3 MoS2 Nd NdCl3 Nd2O3 Nd2(SO4)3 · 8H2O Ne Np NpO2 Ni Ni(C2H3O2)2 · 4H2O Ni(C5H7O2)2 NiBr2 NiCO3 · 2Ni(OH)2

316.76 95.94 335.65 237.75 273.19 209.93 264.00 127.94 143.94 288.07 160.07 144.24 250.60 336.48 720.79 20.180 237.0482 269 58.69 248.86 256.91 218.50 304.12

(II) thiocyanate Molybdenum (III) bromide (IV) chloride (V) chloride (VI) fluoride hexacarbonyl (IV) oxide (VI) oxide (III) sulfide (IV) sulfide Neodymium chloride oxide sulfate 8-water Neon Neptunium (IV) oxide Nickel acetate 4-water acetylacetonate bromide carbonate hydroxide (1/2)

3.71 10.28 4.89 2.928 2.54 1.96 6.47 4.69626 4 5.9115 5.0615 15 7.01 4.134 7.28 2.85 0.8999 g/L0 20.2 11.1 8.90820 1.744 1.45517 5.098 2.6

d 645 explodes 290 d 259 70 d 79 d 100 d 500 d d subl 583 d 165 2622 subl 977 317 194 17.6 150 d d ⬇1100 801 1807 2375 1024 760 1900 d 700– 800 ⫺248.67 644 2547 1453 d 230 963

d ⬎650 subl 140 350 subl

d

: blk HgO, 386 4825 407 268 35.0 subl 1155 d 1867 subl 450 3074 1600 ⫺246.05 ⬎3900 2884 23511atm subl

hyd aq; s HF sl s aq; s alc; dangerously flammable i aq, alc, eth; s KI g/100 mL: 0.00625 aq, 0.8 alc, 0.8 eth, 1.7 acet hyd aq; s HNO3 v s aq; s acet i aq; s HNO3 0.00525 aq; s dil HCl, HNO , I⫺, CN⫺ 0.0625 aq; s HNO3 d aq; s acid i aq; s aqua regia 0.06325 aq; s HCl s hot H2SO4, HNO3, fused KNO3 d alkalis s conc acids s conc acids, dry eth, dry alc hyd aq; s alkalis; 31 g/100 g HF s bz i aq 0.0528 aq; s conc mineral acids, alk d hot HNO3 s aqua regia s hot aq, acids 98 g/100 mL20 aq; s alc s dilute acids 8.87 g/100 mL20 aq 1.05 mL20 aq s HCl

INTERACTIVE

8.95 4.42 7.70 6.28

RIGHT

238.59 284.62 654.99 454.40

(McGHP)

HgF2 Hg(ONC)2 Hg2I2 HgI2

DEAN #37261

3.39

(II) fluoride (II) fulminate (I) iodide (II) iodide

i aq; s HNO3 16 g/100 mL aq; s alc s aq, alc, bz, chl; i eth 100 g/100 mL20 aq s dilute acids

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Melting point, ⬚C

Ni(CO)4 NiCl NiCl2 · 6H2O Ni(CN)2 · 4H2O Ni(HC2H6N2O2)2 Ni3S2 NiF2 Ni(CHO2)2 · 2H2O Ni(NO3)2 · 6H2O NiO Ni2O3 NiSO4 NiSO4 · 6H2O NiS Ni(CO)4

170.73 129.60 237.69 182.79 288.92 240.21 96.69 184.78 290.81 74.71 165.42 154.78 262.86 90.77 170.74

1.31 3.51

⫺19.3 1009

5.87 4.72 2.15420 2.05 7.45 4.83 3.68 2.07 5.3– 5.6 1.318517

anhyd 400 subl 250 790 1450 anhyd 130 56.7 2000 ⫺O2, 600 ⫺SO3, 840 anhyd 280 976 ⫺19.3

Nb NbCl5 NbF5 Nb2O5 N2 15 N2 N2O NO N2O3 N2O4 N2O5 N4Se4 N4S4 NCl3 NF3

92.9064 270.20 187.91 265.82 28.0341 30.01 44.02 30.01 76.02 92.02 108.01 371.87 184.28 120.37 70.01

8.5720 2.75 2.69680 4 4.55 1.165 g/L20 1.25 g/L20 1.843 g/L20 1.249 g/L20 1.447 g/L2 1.44820 4 2.05 4.2 2.2418 1.65320 2.96 g/L20

2468 206 80.0 1512 ⫺210.01 ⫺209.952 ⫺90.81 ⫺163.64 ⫺100.7 ⫺9.3 30 explosive 180 ⫺27 ⫺208.5

Boiling point, ⬚C

43 (expl 60) subl 973

d 2967 1740 d 180– 200 136.7

d 2047 42.3 4860 247.0 234.9 ⫺195.79 ⫺195.73 ⫺88.46 ⫺151.76 2 21.15 d 47.0 185 71 ⫺129.06

Solubility in 100 parts solvent

s EtOH, bz, acet 61 g/100 mL20 aq 100 g/100 mL20 aq; s alc 0.00618 aq; s KCN, NH4OH i aq; s abs alc, dilute acids s HNO3 4 g/100 mL20 aq; i alc, eth s aq; i alc 150 g/100 mL20 aq s acids s hot HCl, HNO3, H2SO4 29 g/100 mL0 aq 40 g/100 mL20 aq s HNO3, KHS explodes 63; FP ⫺4; s organic solvents s fused alkali hydroxides s HCl, CCl4 hyd aq, alc; sl s CS2, CCl4 s HF, hot H2SO4 mL/100 mL: 1.620 aq, 0.112 alc 1300 mL aq; s alc, eth 4.6 mL/100 mL20 aq s eth s conc HNO3, conc H2SO4, chl v s chl; s CCl4 sl s bz, CS2 s organic solvents i aq; s bz, CS2, CCl4

INTERACTIVE

(I) oxide (II) oxide (III) oxide (IV) oxide dimer (V) oxide selenide sulfide trichloride trifluoride

Density

LEFT

Niobium (V) chloride (V) fluoride (V) oxide Nitrogen

Formula weight

(McGHP)

3.40

Nickel (continued) carbonyl chloride chloride 6-water cyanide 4-water dimethylglyoxime (tri-) disulfide fluoride formate 2-water nitrate 6-water (II) oxide (III) oxide sulfate sulfate 6-water sulfide tetracarbonyl

Formula

top of page

short standard

base of DF

O2 OF2 O2F2 O3 Pd Pd(C2H3O2)2 PdCl2 Pd(NO3)2 PdO ClO3F P4 molecules

31.9988 54.00 70.00 48.00 106.42 224.49 177.30 230.42 122.40 102.46 123.8950

P4 PBr5 PCl5 PF5 P4O10 P2S5 PBr3 PCl3 PF3 P4O6 P4Se3 P4S3

(red) hydride, see Phosphine pentabromide pentachloride pentafluoride pentoxide (dimer) pentasulfide tribromide trichloride trifluoride trioxide (dimer) (tetra-) triselenide (tetra-) trisulfide

2.18525 4 2.81 g/L100 2.7 g/L20 22.6120 4.3820 4 4.91

⫺61.5 ⫺132.5 d 73.5 subl 2500.01mm ⫺145 ⫺166.0 3045 32.1 subl 450 40.6

⫺5.5 ⫺59.9 ⫺14.3 ⫺72.4 5225 45.9 130.0

hyd aq; s fuming H2SO4 hyd aq d aq; s H2SO4 d aq d aq d aq s molten alkali or oxidizing fluxes hyd aq slow hyd aq g/100 mL: 7.2425 aq; 37525 CCl4; s bz, eth, alc mL/100 mL20: 3.13 aq, 14.3 alc 6.8 mL/100 mL0 aq

⫺182.96 ⫺145.3 d ⫺ 100 ⫺111.9 3167

8.7020 0.637 g/L 1.82325

⫺218.4 ⫺223.8 ⫺154 ⫺192.5 1555 205 d 680 d 879 d ⫺147.74 44.15

123.8950

2.34

597

subl 416

g/100 mL: 2.86 bz, 2.50 chl, 1.25 CS2; 0.025 abs alc, 1.0 eth i aq; ignites in air, 260

430.56 208.27 125.98 283.88 222.29 270.73 137.35 87.98 219.90 360.80 220.09

3.4620 2.11920 5.805 g/L 2.30 2.09 2.8515 1.57520 4 3.907 g/L 2.13620 4 1.31 2.0317

106 d subl 100 ⫺93.8 340 288 ⫺41.5 ⫺93.6 ⫺151.30 23.8 245– 246 167

166 d ⫺84.6 subl 360 514 173.2 76.1 ⫺101.38 173 (N2 atm) 360– 400 407

d aq; s CCl4, CS2 hyd aq; s CCl4, CS2 hyd aq d aq; s H2SO4 hyd aq; s alkali; 0.22217 CS2 d aq, alc; s acet, CS2 d aq, alc; s bz, chl hyd aq hyd aq; s bz, CS2 flammable in air; s bz, acet, chl, CS2 100 g/100 mL17 CS2; s tolune

1.331 g/L20 2.26 g/L20 1.45bp (lq) 1.998 g/L20 12.02320 4.018

d ⬎680 ⫺46.67 280.3

49.4 mL/100 mL0 aq s hot HNO3, H2SO4 i aq, alc; s acet, chl, eth s alc, acet, HCl s dil HNO3 s 48% HBr; sl s aqua regia

INTERACTIVE

Oxygen difluoride (di-) difluoride Ozone Palladium acetate chloride nitrate oxide Perchloryl fluoride Phosphorus (white)

1.592⫺5 2.788 g/L20

RIGHT

65.47 49.01 127.08 116.83 81.46 65.00 190.2 304.2 332.0 254.20

(McGHP)

NOCl NOF NOHSO4 NO[BF4] NO2Cl NO2F Os OsF6 OsCl4 OsO4

DEAN #37261

3.41

Nitrosyl chloride fluoride hydrogen sulfate tetrafluoroborate Nitryl chloride fluoride Osmium hexafluoride tetrachloride tetraoxide

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short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula

Formula weight

PH4I POClF2

161.91 120.43

POCl2F POBr3 POCl3 Pt PtCl2 PtCl4 PtF6 PtO PtO2 PtS2 Pu PuBr3 PuCl3 PuF3 PuF4 PuF6 PuH2 PuH3 PuO Pu2O3 PuO2 Pu2S3 Po

136.89 286.72 153.35 195.08 266.00 336.90 309.08 211.09 227.09 259.22 239.052 478.79 345.42 296.06 315.05 353.05 241.08 242.08 255.05 526.12 271.05 574.30 208.9824

PoCl4 PoO

350.79 240.98

1.529 g/L

⫺133.81

⫺87.78

2.86 1.6560

18.5 ⫺96.4

subl 62.5 3.1

⫺80.1 56 1.25 1769 d 581 d 370 61.3 d 550 450 d 225 639.5 681 760 1425 1037 d 51.59 ca. 727 ca. 327 1900 2085 (in He) 2390 (in He) 1727 254

52.90 191.7 d 105 3824

1.549720 2.822 1.64525 21.0920 5.87 4.30325 3.826 (lq) 14.915 10.2 7.66 19.81620 4 6.69 5.70 9.32 7.00 4.86 10.40 9.61 13.9 10.2 11.46 9.95 9.196 alpha 9.398 beta

300 (in Cl2) d 550

Solubility in 100 parts solvent mL/100 mL17: 1025 CS2, 726 bz, 319 HOAc, 26 aq; s alc, eth d aq

s bz, CS2, eth d aq, alc s aqua regia, fused alkali i aq, alc; s HCl, NH4OH 143 g/100 mL25 aq

69.14

3230 d ⬎1300 1767 d 2000

i aq; s HCl i aqua regia s HCl, HNO3 i aq; s acids s aq i aq; v s acids hyd aq i aq

62.16

INTERACTIVE

Phosphonium iodide Phosphoryl chloride difluoride dichloride fluoride tribromide trichloride Platinum (II) chloride (IV) chloride (VI) fluoride (II) oxide (IV) oxide (IV) sulfide Plutonium (III) bromide (III) chloride (III) fluoride (IV) fluoride (VI) fluoride (II) hydride (III) hydride (II) oxide (III) oxide (IV) oxide (III) sulfide Polonium (IV) chloride (IV) oxide

34.00

Boiling point, ⬚C

LEFT

PH3

Melting point, ⬚C

(McGHP)

3.42

Phosphine

Density

d 2800 962

sl s aq; s acids

390 (in Cl2)

sl hyd aq; v s HCl; s alc, acet v s dilute HCl

top of page

short standard

base of DF

2.28 1.558 2.48 1.91

⬇325 d 200 859.9 167.5 d 180

K2[PtCl6] K4[Fe(CN)6] · 3H2O

485.99 422.39

3.50 1.85

d 250 anhyd 100

K3[Fe(CN)6] K2[SiF6] K2[ZrF6] K3[Co(NO2)6] · 1.5H2O

329.25 220.27 283.41 479.30

1.89 2.27 3.58

d d

KH KHCO3

40.11 100.11

1.43 2.17

3.27 2.75 2.29 2.32 1.988 2.732 1.98 2.05 1.55 2.67625 4 2.36 2.867 2.338 2.14 2.33

63.38 292 1310 947 ⬇350 734 901 368 771 975 anhyd 180 d ⬇700 634 398 288 d 400 (KPO3) 509 anhyd 300

759

1401 d 370 1435 d to K2O d ⬎400 1437 d 230 1625 d 500

d mp: 1090

1505 d ⬎mp

d

d aq to KOH; s acids g/100 mL: 200 aq, 34 alc 19 g/100 mL aq; slowly s glyc; s alc 71 g/100 mL30 aq 6.9 g/100 mL20 aq g/100 mL: 6520 aq, 22 glyc, 0.4 alc 90 g/100 mL20 aq; i alc g/100 mL: 7.320 aq, 2 glyc g/100 mL: 3420 aq, 7 glyc, 0.4 alc 64 g/100 mL20 aq; i alc g/100 mL: 154 aq; 40 glyc s aq; sl s alc g/100 mL: 50 aq, 50 glyc, 4 MeOH 11.7 g/100 mL20 aq 25 g/100 mL30 aq g/100 mL: 196 aq, 63 glyc; i alc 22.6 g/100 mL20 aq; i alc v s aq with decomposition s aq; i alc s aq; flammable if ground s aq v s aq 95 g/100 mL20 aq 250 g/100 mL aq v s aq; i alc, bz, chl d aq; s alkali iodide solutions 0.4820 aq 28 g/100 mL20 aq

d 200

40 g/100 mL20 aq (slow); sl s alc sl s aq; i alc 2.7 g/100 mL20 aq 0.08918 aq; s HOAc; v sl s alc

417 d d ⬎100

d aq 34 g/100 mL20 aq; i alc

INTERACTIVE

0.89 1.57 2.8

RIGHT

39.0983 98.14 256.21 81.91 167.00 119.00 138.21 122.55 74.55 194.19 324.42 81.11 65.12 294.19 199.01 180.03 136.09 71.10 384.38 222.32 254.32 160.30 58.10 84.12 234.25 1253.82

(McGHP)

K KC2H3O2 K3AsO4 KBO2 KBrO3 KBr K2CO3 KClO3 KCl K2CrO4 K3C6H5O7 · H2O KOCN KCN K2Cr2O7 K[Ag(CN)2] KH2AsO4 KH2PO4 KO2 K4P2O7 · 3H2O K2S2O5 K2S2O7 KOCSSC2H5 KF KCHO KC6H11O7 K4[BiI7]

DEAN #37261

3.43

Potassium acetate arsenate borate(1⫺) bromate bromide carbonate chlorate chloride chromate(VI) citrate hydrate cyanate cyanide dichromate(VI) dicyanoargentate(I) dihydrogen arsenate dihydrogen phosphate dioxide diphosphate(V) 3-water disulfate(IV) disulfate(VI) (pyrosulfate) ethyldithiocarbonate fluoride formate gluconate heptaiodobismuthate(III)(4⫺) hexachloroplatinate(IV) hexacyanoferrate(II) 3-water hexacyanoferrate(III) hexafluorosilicate hexafluorozirconate hexanitritocobaltate(III) 1.5-water hydride hydrogen carbonate

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short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Density

78.10 174.18 204.22 136.17 72.17 188.18 56.11 214.00 166.00 197.13 238.14 101.10 85.10 184.23 94.20 354.18

2.37

KClO4 KIO4 KMnO4 K2O2 K2C2O6 · H2O K2S2O8 KReO4 KC6H4(OH)SO3 · H2O K3PO4 KSeCN K2SiO3 K2Na[Co(NO2)6] · H2O

Boiling point, ⬚C

238.80 d to K2P2O7 d 197 ⬇455

d 477

1323

2.3 2.11 1.915 2.13 2.35

406 560 d 681 190 d 919 333 441 anhyd 160 350 d

138.55

2.52

d 400

230.010 158.03 110.20 216.24 270.32 289.30 240.28 212.27 144.08 154.29 454.18

3.618 2.7

582 d 240 : O2 490

2.48 4.38 1.87 2.56417 4

d 100 555

1.636 2.24 1.70 1.956 2.044 3.89 3.12

1.633

1340 d 100 976 d 135

d to K2S2O7

1345 d 1400 d 400 d 350 d to K2CO3

1370

Solubility in 100 parts solvent

39 g/100 mL20 aq; s alc 150 g/100 mL aq 8.3 g/100 mL aq; sl s alc 48 g/100 mL20 aq s aq, alc 0.520 aq; s acids; v sl s alc g/100 mL: 11220 aq, 33 alc, 40 glyc 8.1 g/100 mL20 aq; i alc g/100 mL: 14420 aq, 4.5 alc, 50 glyc s aq; stable in KOH 160 g/100 mL aq g/100 mL: 3220 aq, 0.16 alc, s glyc 306 g/100 mL20 aq; sl s alc 36 g/100 mL20 aq d aq to KOH, s alc v s aq 2.0425 aq; 0.003625 BuOH; 0.0013 EtOAc 0.4220 aq, sl s KOH 6.34 g/100 mL20 aq; d HCl d aq 6.5 g/100 mL aq; d hot aq 2.5 g/100 mL20 aq; i alc 0.9920 aq s aq, alc 50.8 g/100 mL20 aq; i alc s aq s aq 0.07 aq

INTERACTIVE

KHF K2HPO4 KHC8H4O4 KHSO4 KHS KHC4H4O6 KOH KIO3 KI K2MnO4 K2MoO4 KNO3 KNO2 K2C2O4 · H2O K2O K2[TiO(C2O4)2(H2O)2]

Melting point, ⬚C

LEFT

periodate permanganate peroxide peroxodicarbonate hydrate peroxodisulfate perrhenate phenolsulfonate hydrate phosphate selenocyanate silicate(2⫺) sodium hexanitritocobaltate(III) hydrate

Formula weight

(McGHP)

3.44

Potassium (continued) hydrogen difluoride hydrogen phosphate hydrogen phthalate hydrogen sulfate hydrogen sulfide hydrogen tartrate hydroxide iodate iodide manganate(VI) molybdate(VI) nitrate nitrite oxalate hydrate oxide oxobisoxalatodiaquatitanate(IV) perchlorate

Formula

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short standard

base of DF

K2[HgI4] KSCN K2S2O3 KH3(C2O4) · 2H2O

786.48 97.18 190.33 254.20

K3[Sb(C2O4)3] K2CS3 K(UO2 )(C2H3O2 )2 · H2O Pr PrCl3 Pr2O3

503.12 186.41 504.28 140.9077 247.27 329.81

(IV) Promethium-147 bromide chloride Protoactinium (IV) chloride (V) chloride Radium bromide chloride Radon

PrO2 Pm PmBr3 PmCl3 Pa PaCl4 PaCl5 Ra RaBr2 RaCl2 Rn

172.91 146.915 386.7 153.4 231.0359 372.85 408.31 226.03 385.88 296.93 222.0

70– 80 d ⬎270 anhyd 140

anhyd 130– 140

2.66 1.74

1069 948 d anhyd 155

1670

1.98 3.75 2.50520 4 1.11 3.35921 4

d 357 530 d 497

1.89

173 d 400 d

1.836

d 3.29615 anhyd 275 6.475 ␣-form 935 4.0 769 to 782 7.07 oxidizes to Pr6O11 6.82 tr 350 to Pr6O11 7.22 1080 5.38 727 737 15.37 1568(8) 4.72 subl 400 3.74 301 5.5 700.1 5.79 728 4.91 1000 9.73 g/L ⫺71

d 200

d 500

3520 1710

3000 est 1667 1670 4227 420 1737 subl 900 ⫺62

54 g/100 mL15 aq g/100 mL: 58.220 aq, 6.5 alc 100 g/100 mL20 aq; i alc readily soluble hot aq or alc g/100 mL: 1120 aq, 1.3 glyc, i alc 28.6 g/100 mL20 aq 138 g/100 mL20 aq s aq 61.8 g/100 mL20 aq 0.4520 aq g/100 mL: 2125 aq, 3.520 MeOH g/100 mL: 13715 aq, 7115 alc, 4 eth v s aq; s alc, acet, eth g/100 mL: 21720 aq, 200 acet, 8 alc 155 g/100 mL20 aq; i alc 1.8 aq a aq v s aq s aq s hot water and acids 104 g/100 mL13 aq; s alc i aq; s acids

s aq s aq

INTERACTIVE

tetraiodomercurate(II) thiocyanate thiosulfate trihydrogen bisoxalate 2-water trisoxalatoantimonate(III) trithiocarbonate uranyl(VI) acetate hydrate Praseodymium chloride (III) oxide

1.790 1.36325 20 3.197

RIGHT

282.23 150.22 298.94 322.57 174.26 110.26 194.29 235.28 253.79 377.88 125.90 53.94 698.21

(McGHP)

KNaC4H4O6 · 4H2O KC6H7O2 K2SnO3 · 3H2O KOOCC17H35 K2SO4 K2S K2SO3 · 2H2O K2C4H4O6 · 0.5H2O K2TeO3 K[AuCl4] K[BF4] K[BH4] K4[CdI4] · 2H2O

DEAN #37261

3.45

sodium tartrate 4-water sorbate stannate(IV) 3-water stearate sulfate sulfide sulfite 2-water tartrate hemihydrate tellurate(IV) tetrachloroaurate(III) tetrafluoroborate tetrahydridoborate tetraiodocadmate 2-water

i aq; s HCl hyd aq; s THF, CH3CN d aq; s acids s aq s aq 23 mL/100 mL20 aq; s org solv

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula weight

Rb RbC2H3O2 RbBr Rb2CO3 RbClO3 RbCl RbH2PO4 RbF Rb2[PtCl6] RbOH RbI RbNO3 Rb2O Rb2SO4 Ru RuCl3 RuF5 RuO2

85.4678 144.52 165.37 230.95 168.94 120.92 182.47 104.47 578.75 102.47 212.37 147.47 186.93 267.00 101.07 207.43 196.06 133.07

21.02 5.38 3.58 3.65 6.9– 7.4 6.1 4.866 3.309 12.4120 5.38 5.4 8.20

1.532 3.35 3.184 2.76 3.2 3.94 3.20 3.55 3.11 4.0 3.5 12.4520 4 3.11 3.90 6.97

Boiling point, ⬚C

3180 4.5 124.5 18.5 48.3 disprop 400 300.3 d 460 29.3 1963 d 450 subl 600 d 1100 124– 125

5678 128 795 33.8 73.7 750 360.3

39.31 246 682 837 342 715 840 833 d 301 642 305 400 d 1050 2334 d ⬎500 86.5 d

691

225 3727

1346 d 900 1390 1410

1304

4150 227

Solubility in 100 parts solvent s HNO3 hyd in water to HReO4; s CCl4 hyd aq 52.5 g/100 mL anhyd HF; s HNO3 hyd aq s HNO3 v s aq, org solv i aq; s HNO3 hyd aq; s CCl4 s fused KHSO4 i aq; s KOH, KCN i acids, alkalis i aq reg, KOH s org solv except hydrocarbons d aq to RbOH 86 g/100 mL45 aq 108 g/100 mL20 aq g/100 mL: 45020 aq, 0.7419 alc 5.4 g/100 mL20 aq g/100 mL: 9120 aq, 1.1 MeOH s aq 131 g/100 mL18 aq 0.02820 aq 180 g/100 mL18 aq; s alc 163 g/100 mL25 aq; s alc l9.5 g/100 mL20 aq s aq : RbOH 48 g/100 mL20 aq s fused alkali, oxidizing fluxes i aq; s HCl, alc d aq i aq; s fused alkali

INTERACTIVE

186.207 269.66 262.20 300.20 319.20 234.20 484.41 596.88 344.02 102.9055 209.26 159.90 253.81 388.76

Melting point, ⬚C

LEFT

Re ReClO3 ReF4 ReF6 ReF7 ReO3 Re2O7 Re2S7 ReCl4O Rh RhCl3 RhF3 Rh2O3 Rh2(CO)4Cl2

Density

(McGHP)

3.46

Rhenium chloride trioxide (IV) fluoride (VI) fluoride (VII) fluoride (VI) oxide (VII) oxide (VII) sulfide (VI) tetrachloride oxide Rhodium (III) chloride (III) fluoride (III) oxide tetracarbonyldi-␮-chlorodichloride Rubidium acetate bromide carbonate chlorate chloride dihydrogen phosphate fluoride hexachloroplatinate(IV) hydroxide iodide nitrate oxide sulfate Ruthenium (III) chloride (hexagonal) (V) fluoride (IV) oxide

Formula

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short standard

base of DF

1074 855 682 1306 2335 anhyd 450 1541 967 2485 anhyd 250 217 123 305

(tetra-) tetrasulfide Silane chlorodichloroiodotrichloroSilicon carbide (beta) dioxide (␣ quartz)

Se4S4 SiH4 SiH3Cl SiH2Cl2 SiH3I SiHCl3 Si SiC SiO2

444.10 32.12 66.56 101.01 158.01 135.45 28.0855 40.10 60.08

3.20 1.409 g/L 2.921 g/L 4.432 g/L 2.035 1.331 2.33 3.16 2.648

113 d ⫺185 ⫺118 ⫺122 ⫺57 ⫺128 1412 2830 573 tr ␤ quartz

dioxide - tungsten trioxide - SiO2 · 12WO3 · 26H2O water (silicotungstic acid) disulfide SiS2

41.6 ⫺85 8.5 15 ⫺10 ⫺34.6 121.5 340

3310.66 92.22

1794 2030 d 2427

2836 967 d 550 685 subl 196 225 d 217 d 127 dec 177.2 125 106

subl 315

⫺111.9 ⫺30.4 8.3 45.5 33 3265 2950

s acids s aq dec; i alc 93.4 g/100 mL20 aq i aq; s H2SO4 s acids 2.7 g/100 mL20 aq d aq v s aq; i alc s hot or conc acids 54.6 g/100 mL25 aq s eth, KOH, KCN; i aq, alc d aq; s HBr, chl, CS2 d aq d aq; s chl, CS2 d aq d aq; s bz, chl, CS2 d aq; misc bz, chl, CCl4, CS2 d aq reacts aq viol; misc alc, eth; s chl s CS2; 1.2 g/100 mL20 bz w/w %: 3814 aq, 1012 MeOH, 4.35 acet, 6.714 EtOH, 1.112 HOAc; s H2SO4 i aq; 0.04 g/100 mL20 bz; s CS2 d aq slowly; i alc, bz, chl, eth d aq d aq d aq; s bz, chl s HF ⫹ HNO3, fused alkali oxides s fused alkali oxides i aq; s HF

INTERACTIVE

7.52 3.687 4.46 6.643 8.347 2.93 2.985 hex 2.39 3.864 2.519 4.8120 4 4.029 2.6 3.60415 4 3.3850 2.77425 4 2.44 2.8 2.75 8.467 g/L 2.44 3.95

RIGHT

150.36 221.27 256.72 207.36 348.72 733.03 44.956 151.31 137.91 468.17 78.96 398.58 220.77 317.73 254.77 228.83 165.867 132.96 154.95 192.95 350.32 110.96

(McGHP)

Sm SmCl2 SmCl3 SmF3 Sm2O3 Sm2(SO4)3 · 8H2O Sc ScCl3 Sc2O3 Sc2(SO4)3 · 5H2O Se SeBr4 SeCl4 Se2Br2 SeBr2O Se2Cl2 SeCl2O SeF2O SeF4 SeF6 Se2S6 SeO2

DEAN #37261

3.47

Samarium (II) chloride (III) chloride (III) fluoride (III) oxide (III) sulfate 8-water Scandium chloride oxide sulfate 5-water Selenium (hexagonal) (IV) bromide (IV) chloride (di-) dibromide dibromide oxide (di-) dichloride dichloride oxide difluoride oxide (IV) fluoride (VI) fluoride (di-) hexasulfide (IV) oxide

v s aq, alc 2.04

1090

s d aq, alc; i bz

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

3.48

Silicon (continued) tetrabromide tetrachloride tetrafluoride tetraiodide (tri-) tetranitride Silver acetate antimonide azide bromide carbonate chlorate chloride

Formula

Formula weight

chromate(VI) cyanide fluoride (II) fluoride iodate

Ag2CrO4 AgCN AgF AgF2 AgIO3

iodide (alpha) nitrate nitrite oxalate oxide (II) oxide perchlorate permanganate

AgI AgNO3 AgNO2 Ag2C2O4 Ag2O AgO AgClO4 AgMnO4

2.81 1.5 4.567 g/L 4.1 3.17 10.49 3.259 4.9 6.473 6.077 4.43020 4 5.56

5.2 ⫺68.8 ⫺90.3 120.5 1878 961.78 d 559 exp ⬃252 432 218 231 455

331.73 133.89 126.87 145.87 282.77

5.62525 3.95 5.852 4.57 5.52520

320 d 435 690 ⬎200

234.77 169.87 153.87 303.76 231.73 123.87 207.32 226.80

5.68330 4.35219 4.453 5.034 7.2225 4 7.48325 4 2.80625 4.49

558 212 d ⬎140 explodes 140 d 200 (d light) d ⬎100 d 486 d by light

Boiling point, ⬚C

154 57.6 ⫺86 287.3 2164

1500 d 270 1547

⬇1150 d 700 d 1505 d 440

Solubility in 100 parts solvent

hyd aq viol hyd aq; s bz, CCl4, eth hyd aq; s HF d aq; 2.2 g/100 mL27 CS2 i aq; s HF s HNO3 1.0420 aq; s dil HNO3 i aq; s KCN, HNO3 (explosive) i aq; s KCN 0.00320 aq; s KCN, HNO3, NH4OH 10 g/100 mL15 aq i aq; 7.7 g/100 mL NH4OH, KCN, Na2S2O3 0.00220 aq; s HNO3, NH4OH i aq; s KCN 182 g/100 mL20 aq; s HF, CH3CN hyd viol aq 0.05325 aq; 40 g/100 mL 10% NH4OH i aq; s KCN, KI, (NH4)2CO3 g/100 mL: 21620 aq, 3.3 alc, 0.4 acet 0.3325 aq; d dilute acids 0.00420 aq; s HNO3, NH4OH 0.00225 aq; s dil HNO3, NH4OH i aq; d alk and acids 557 g/100 mL20 aq; s bz, glyc, pyr 0.9 aq; d alc

INTERACTIVE

347.70 169.90 104.08 535.70 140.28 107.8682 166.91 445.35 149.89 187.77 275.75 191.32 143.32

Melting point, ⬚C

LEFT

SiBr4 SiCl4 SiF4 SiI4 Si3N4 Ag AgC2H3O2 Ag3Sb AgN3 AgBr Ag2CO3 AgClO3 AgCl

Density

(McGHP)

Name

top of page

short standard

base of DF

849

selenate(IV) sulfate

Ag2SeO3 Ag2SO4

342.69 311.80

5.93 5.45

530 660

d ⬎530 d 1085

Ag2S Na NaC2H3O2 NaC2H3O2 · 3H2O NaAlO2 NaAl(SO4)2 · 12H2O NaNH2 NaNH4HPO4 · 4H2O

247.80 22.98977 82.03 136.08 81.97 458.28 39.01 209.07

7.23420 4 0.96820 1.528 1.45 4.63 1.61 1.39 1.54

845 97.82 324 anhyd 120 1650 ⫺60 210 ⬇80

d 881.4

NaAsO2 NaC6H7O6 NaN3 NaO2C6H5 NaBiO3 Na3Bi NaBrO3 NaBr Na2CO3 Na2CO3 · H2O Na2CO3 · 10H2O Na2CO3 · NaHCO3 · 2H2O NaClO3 NaCl NaClO2 Na2CrO4 Na3C6H5O7 · 2H2O NaOCN NaCN Na[BH3CN]

129.91 198.11 65.01 144.11 279.96 277.95 150.89 102.89 105.99 124.00 286.14 226.02

1.87

sulfide (agentite) Sodium acetate acetate 3-water aluminate(1⫺) aluminum sulfate 12-water amide ammonium phosphate 4-water arsenate(III)(1⫺) ascorbate azide benzoate bismuthate(V)(1⫺) bismuthide bromate bromide carbonate carbonate hydrate carbonate 10-water carbonate - hydrogen carbonate 2-water (trona) chlorate(V) chloride chlorite chromate(VI) citrate 2-water cyanate cyanide cyanohydridoborate

106.44 58.44 90.44 161.97 294.10 65.01 49.01 62.84

1.84620

3.34 3.20020 4 2.53320 2.25 1.46 2.112 2.5 2.17 2.72 1.89 1.6 1.12

d ⬎120

subl 400 anhyd ⬎280

d 218 d to Na ⫹ N2 d 766 381 d 755 858.1 anhyd 100 34 d

248 800.8 d 180– 200 792 anhyd 150 550 563 ⬎240 d

1390 d

d ⬎300 : O2 1465

0.006 aq; v s dil HNO3, KCN, (NH4)2CO3 sl s aq; s HNO3 0.8020 aq (slow); s HNO3, NH4OH, H2SO4 i aq; s HNO3, alk CN’s d aq to NaOH 75 g/100 mL20 aq g/100 mL: 12520 aq, 5.1 alc v s aq; i alc 110 g/100 mL15 aq; i alc d ⬎500, reacts aq viol 14.3 g/100 mL aq v s aq; sl s alc 62 g/100 mL20 aq 41 g/100 mL20 aq; 0.3 alc g/100 mL: 6325 aq; 1.3 alc i cold aq; dec by hot aq & acids d aq 40 g/100 mL20 aq; i alc g/100 mL: 9020 aq, 6 alc; 16 MeOH 29 g/100 mL20 aq; s glyc; i alc g/100 mL: 33 aq, 14 glyc; i alc 50 g/100 mL aq; s glyc 13 g/100 mL0 aq g/100 mL: 9620 aq, 0.77 alc, 25 glyc g/100 mL: 3620 aq, 10 glyc 34 g/100 mL17 aq 84 g/100 mL20 aq 77 g/100 mL25 aq; i alc s aq d; 0.220 alc 58.7 g/100 mL20 aq g/100 mL: 212 aq, 37.2 THF; v s NaOH; i bz, eth

INTERACTIVE

6.37

RIGHT

418.62

(McGHP)

Ag3PO4

DEAN #37261

3.49

phosphate

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula weight

Density

Melting point, ⬚C

3.50

2.34825 4

diethyldithiocarbamate dihydrogen arsenate(V) hydrate dihydrogen diphosphate(V) dihydrogen phosphate(V) dihydrate dimethylarsonate 3-water (cacodylate) dioxide diphosphate(V) dithionate(V) 2-water

NaS2CN(C2H5)2 · 3H2O NaH2AsO4 · H2O

225.31 181.94

2.53

anhyd 100; mp 356 anhyd 94– 96 anhyd 130

Na2H2P2O7

221.94

1.9

d 220

NaH2PO4 · 2H2O

156.01

1.91

anhyd 100

NaO2As(CH3)2

214.03

NaO2 Na4P2O7 Na2S2O6 · 2H2O

54.99 265.90 242.14

dithionate(III) diuranate(VI) dodecylbenzenesulfonate dodecylsulfate ethoxide ethylenebis(iminodiacetate) (EDTA) ethylsulfate fluoride formate gluconate glycerophosphate hexachloroplatinate(IV) 6-water

Na2S2O4 Na2U2O7 NaO3SC6H4C12H25 NaO3SOC12H25 NaOC2H5 (NaOOCCH2)2NC2H4N(CH2COONa)2 NaO3SOC2H5 NaF NaHCO2 NaC6H11O7 Na2C3H5(OH)2PO4 Na2[PtCl6] · 6H2O

174.11 634.03 348.49 288.38 68.06 380.20 148.12 41.99 68.01 218.14 216.04 561.88

d 400

73.1 g/100 mL20 aq

d 200

s aq, alc s aq 4.5 g/100 mL0 aq

d NaPO3, 200

anhyd 120

2.53 2.19

552 988 anhyd 110

g/100 mL: 200 aq, 40 alc

d 267 to Na2SO4 ⫹ SO2

10 g/100 mL aq d aq; s abs alc 103 g/100 mL aq

⬎300

996 253

2.50

d ⬎130 ⫺6H2O, 110

2.260 aq 13.4 g/100 mL20 aq; i alc

22 g/100 mL20 aq; sl s alc i aq; s acids

d

2.78 1.92

71 g/100 mL0 aq; i alc

1704 d ⬎253

140 g/100 mL aq; s alc 4 g/100 mL15 aq; i alc 81 g/100 mL20 aq; s glyc; sl s alc 59 g/100 mL25 aq; sl s alc; i eth 67 g/100 mL aq; i alc v s aq; s alc

INTERACTIVE

298.00

Solubility in 100 parts solvent

LEFT

Na2Cr2O7 · 2H2O

Boiling point, ⬚C

(McGHP)

Sodium (continued) dichromate 2-water

Formula

top of page

short standard

base of DF

anhyd 82

d 435

28 g/100 mL20 aq

Na4[Fe(CN)6] · 10H2O

484.06

Na3[Fe(CN)6] · H2O

298.93

Na3[AlF6] Na3[Co(NO2)6] NaH

209.94 403.98 24.00

2.97

1009

1.39

425 d

Na2HAsO4 · 7H2O

312.01

1.87

anhyd 130

d 150

NaHCO3 NaHF2 Na2HPO4 · 7H2O

84.01 62.00 268.07

2.20 2.08 1.7

to Na2CO3 d ⬎160 d

270

8 g/100 mL20 aq; i alc 3.7 g/100 mL20 aq 25 g/100 mL40 aq; v sl s alc

NaHSO4 NaHS NaHSO3 NaOH

120.06 56.06 104.06 40.00

2.435 1.79 1.48 2.130

315 350 d 323

d

1388

63– 64

d ⬎64

50 g/100 mL20 aq; d alc s aq, alc, eth g/100 mL: 29 aq, 1.4 alc g/100 mL: 10820 aq, 14 abs alc, 24 MeOH; s glyc v s aq; i abs alc, bz, eth

d by CO2 from air

18.9 g/100 mL0 aq

154.12

NaClO · 5H2O

164.52

1.6

18

iodate iodide

NaIO3 NaI

197.89 149.89

4.28 3.67

d 660

lactate methoxide molybdate(VI) 2-water nitrate nitrite oxalate oxide pentacyanonitrosylferrate(III) 2-water (nitroprusside)

NaOOCCHOHCH3 NaOCH3 Na2MoO4 · 2H2O NaNO3 NaNO2 Na2C2O4 Na2O Na2[Fe(CN)5NO] · 2H2O

112.06 54.02 241.95 85.00 69.00 134.00 61.98 297.65

⬇3.5 2.26 2.17 2.34 2.27 1.72

d ⬎300 anhyd 100 307 271 d ⬇250 dull red heat

1304

mp 687 d ⬇500 d ⬎320 d ⬎400

29 g/100 mL0 aq 8.1 g/100 mL20 aq g/100 mL: 20020 aq, 100 glyc, 50 alc; s acet misc aq, alc d aq; s alc 65 g/100 mL20 aq g/100 mL: 8820 aq, 0.8 alc 67 g/100 mL20 aq 3.4 g/100 mL20 aq; i alc d aq to NaOH violently 40 g/100 mL16 aq

INTERACTIVE

Na[HOCH2SO2] · 2H2O

RIGHT

hydroxymethanesulfinate dihydrate hypochlorite 5-water

s aq v s aq; sl s alc ign spontaneously moisture; d alc viol 61 g/100 mL15 aq; s glyc; sl s alc

(McGHP)

3.51

hydrogen arsenate(V) 7-water hydrogen carbonate hydrogen difluoride hydrogen phosphate 7-water hydrogen sulfate hydrogen sulfide hydrogen sulfite hydroxide

1.46

DEAN #37261

hexacyanoferrate(II) 10-water hexacyanoferrate(III) hydrate hexafluoroaluminate hexanitritocobaltate(III) hydride

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

3.52

Density

Melting point, ⬚C

122.44

2.52

480 d

KIO4 Na2O2 NaBO3 · 4H2O Na2S2O8 NaReO4 Na3PO4 Na3PO4 · 12H2O NaPH2O2 · H2O NaOOCC2H5 NaOOCC6H4OH Na2SeO4 Na2SiO3 Na2SiO3 · 5H2O Na4SiO4 Na2SnO3 · 3H2O NaOOCC17H35 Na2SO4 Na2SO4 · 10H2O Na2S Na2S · 9H2O Na2SO3 Na2C4H4O6 · 2H2O Na2B4O7 Na2B4O7 · 10H2O

213.89 77.98 153.88 238.11 273.19 163.94 380.12 105.99 96.06 160.10 188.94 122.06 212.14 184.04 266.71 306.47 142.04 322.20 78.05 240.18 126.04 230.08 201.22 381.37

3.865 2.805

d ⬇300 675 d ⬎60 d 300 1340 73.4 anhyd 200

Na[AlCl4] Na[AuCl4] · 2H2O Na[BF4] Na[BH4]

191.78 397.80 109.82 37.83

5.24 2.537 1.62

3.098 2.614 1.749

2.7 1.46 1.856 1.43 2.63 1.82 2.4 1.73 2.01 2.47 1.074

1089 72.2 1018 d 140 (slow) d 8800 32.4 1172 vacuo d ⬇50 d anhyd ⬃120 742.5 75 d 151 d ⬎100 384 497

Solubility in 100 parts solvent

anhyd 320

g/100 mL25; 114 aq, 1.5 BuOH, 8.4 EtOAc 10.3 g/100 mL20 aq v s aq (dec) 2.5 g/100 mL aq 55 g/100 mL aq; d by alc 33 g/100 mL20 aq 12.1 g/100 mL20 aq 28.3 g/100 mL20 aq; i alc 100 g/100 mL20 aq; s glyc, alc g/100 mL25: 100 aq, 4.1 alc g/100 mL: 11020 aq, 11 alc, 25 glyc 27 g/100 mL20 aq s aq; hyd by hot aq; i alc v s aq s aq 59 g/100 mL20 aq; i alc sl s aq 28 g/100 mL20 aq 67 g/100 mL25 aq; s glyc; i alc 18.6 g/100 mL20 aq; sl s alc 200 g/100 mL aq; sl s alc 31 g/100 mL20 aq; s glyc; i alc 29 g/100 mL6 aq; i alc 2.620 aq g/100 mL: 6.3 aq, 100 glyc

d d 315

s aq 166 g/100 mL27 aq; s alc, chl 108 g/100 mL27 aq 1825 DMF; 16.420 MeOH (reacts)

d

⫺11H2O, 100 d to PH3

anhyd 100

d 2227 anhyd 100

INTERACTIVE

NaClO4

Boiling point, ⬚C

LEFT

periodate peroxide peroxoborate 4-water peroxodisulfate(VI) perrhenate phosphate phosphate 12-water phosphinate hydrate propanoate salicylate selenate(VI) silicate(2⫺) metasilicate(2⫺) 5-water silicate(4⫺) stannate(IV) 3-water stearate sulfate sulfate 10-water sulfide sulfide 9-water sulfite tartrate dihydrate tetraborate tetraborate 10-water (borax) tetrachloroaluminate tetrachloroaurate tetrafluoroborate tetrahydridoborate

Formula weight

(McGHP)

Sodium (continued) perchlorate

Formula

top of page

short standard

base of DF

254.52 158.53 203.61 125.62 183.60 121.64 437.43 341.43 319.81 211.63 103.62 286.52

2.99 4.7 3.0025

peroxide sulfate sulfide Sulfinyl bromide (Thionyl) chloride fluoride Sulfonyl chloride (Sulfuryl) diamide fluoride

SrO2 SrSO4 SrS SOBr2 SOCl2 SOF2 SO2Cl2 SO2(NH2)2 SO2F2

119.62 183.68 119.69 207.87 118.97 86.06 134.97 96.11 102.06

4.78 3.96 3.70 2.68820 4 1.638 3.776 g/L 1.667420 4 1.807 4.478 g/L

215 d 1607 2227 ⫺52 ⫺104.5 ⫺129.5 ⫺54.1 93 ⫺135.8

Sulfur (gamma) (alpha) orthorhombic

S S8

32.066 256.53

1.92 2.0820

256.53

1.96

106.8 tr 94.5 to beta form 115.21

(beta) monoclinic tr slowly S8 to rhombic

2.64 4.216 3.5 3.152 3.052 3.89 4.24 3.544 3.625 5.04515 4.42

anhyd 100 53 anhyd 100

d ⬎100 anhyd 100 mp: 695.6

757 657 d 1100 to SrO ⫹ CO2 120 d : O2 874 d 1477

1366 2045

535

⫺H2O, 744

402 anhyd 150 570 2430

1773 d

134 g/100 mL20 aq s aq; i alc 70 g/100 mL20 aq (dec slowly) 22 g/100 mL aq; i alc 88 g/100 mL0 aq; i alc s hot aq d to Sr(OH)2 in water 100 g/100 mL20 aq i aq; s acids

444.72 444.6

167 g/100 mL20 aq 52.9 g/100 mL20 aq 0.1220 aq; s HCl 0.01120 aq; s hot HCl i aq; s acids 0.820 aq 0.0315 aq 178 g/100 mL20 aq; s alc 33 g/100 mL aq 69.5 g/100 mL20 aq; sl s alc, acet 0.6920 aq g/100 mL25: 157 aq, 71 BuOH, 77 EtOAc, 90 acet 0.01820 aq; d hot aq 0.01320 aq; sl s acid sl s aq; s acid (dec) hyd aq (slow); misc bz, chl, CCl4 hyd aq; misc bz, chl, CCl4 hyd aq; s bz, chl, eth hyd aq; misc bz, eth, HOAc s aq, hot EtOH, acet mL gas/100 mL: 4 aq, 24 alc, 136 CCl4, 210 toluene 23 g/100 mL0 CS2; s alc, bz i aq; s organic solvents

444.6

23 g/100 mL0 CS ; s alc, bz

1250 2460

645

140 76 ⫺43.8 69.3 d 250 ⫺55.38

INTERACTIVE

Sr(ClO3)2 SrCl2 SrCrO4 SrF2 SrHPO4 Sr(OH)2 Sr(IO2)2 SrI2 Sr(OOCCHOHCH3)2 · 3H2O Sr(NO3)2 SrO Sr(ClO4)2

chlorate chloride chromate(VI) fluoride hydrogen phosphate hydroxide iodate iodide lactate 3-water nitrate oxide perchlorate

287 2.345 1.69 1.786 3.25

RIGHT

81.07 158.11 248.19 414.04 329.85 121.93 87.62 247.43 147.63

(McGHP)

3.53

NaSCN Na2S2O3 Na2S2O3 · 5H2O (NaPO3)3 · 6H2O Na2WO4 · 2H2O NaVO3 Sr SrBr2 SrCO3

DEAN #37261

thiocyanate thiosulfate thiosulfate 5-water trimetaphosphate 6-water tungstate(VI) dihydrate vanadate(V) Strontium bromide carbonate

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

3.54

Density

Melting point, ⬚C

Boiling point, ⬚C

Solubility in 100 parts solvent

S2F10 ClSSCl SCl2 SO2

254.11 135.04 102.97 64.07

2.08 1.688 1.622 2.811 g/L

⫺52.7 ⫺77 ⫺122 ⫺75.47

30 137 59.5 ⫺10

SF6 SF4 SO3 SO3 SO3

146.06 108.06 80.06 80.06 80.06

6.409 g/L 4.742 g/L

⫺50.8 ⫺121.0 62.3 32.5 16.8

subl ⫺63.8 ⫺38 vp 73mm at 25 vp 344mm at 25 44.8 v s aq (slow)

Ta TaBr5 TaC Ta2C TaCl5 TaB2 TaF5 TaI TaN Ta2O5 Tc TcF6 TcO2 Tc2O7 Te TeBr TeCl2 TeCl4 TeF4 TeF6

180.9479 580.47 192.96 373.91 358.21 202.57 275.94 815.47 194.95 441.89 97.9072 212.91 130.91 309.81 127.60 447.22 198.51 269.41 203.59 241.59

2996 265 3880 3327 216 3140 96.8 496 3090 1785 2157 37.4 subl 1000 119.5 449.8 380 208 225 129 ⫺37.68

5429 349 4780

s HF, fused alkali (slowly) hyd aq; s abs alc, eth sl s HF

239.3

hyd aq; s abs alc

229.5 543

s aq, eth, conc HNO3 hyd aq; s eth sl s aq reg; reacts alkalis s HF; d fused KHSO4 or KOH s HNO3, aq reg, conc H2SO4 s HCl s acid, alkali s aq s HNO3, KOH, conc H2SO4 s HBr, eth, HOAc disprop with eth, diox; s acid hyd aq; s HCl, abs alc, bz d aq hyd aq, KOH

1.92 16.69 4.99 14.3 15.1 3.68 11.2 4.7420 5.80 13.7 8.2 11 3.0 6.9

10.601 g/L

310.6 989.9 ⬇20 d 328 380 d ⬎195 subl ⫺38.9

INTERACTIVE

6.24 4.3 6.9 3.0

4265 55.3

d fusion with KOH hyd aq; s alc, bz, eth, CS2, CCl4 hyd aq mL/100 mL: 393720 aq, 25 alc, 32 MeOH; s chl, eth sl s aq; s alc, KOH d aq viol; v s bz stable modification

LEFT

hexafluoride tetrafluoride trioxide (alpha) (beta) (gamma) Sulfuryl, see Sulfonyl Tantalum (V) bromide carbide (di-) carbide (V) chloride diboride (V) fluoride (V) iodide nitride (V) oxide Technetium-98 (VI) fluoride (IV) oxide (VII) oxide Tellurium (IV) bromide (II) chloride (IV) chloride (IV) fluoride (VI) fluoride

Formula weight

(McGHP)

Sulfur (continued) (di-) decafluoride (di-) dichloride dichloride dioxide

Formula

top of page

short standard

base of DF

302.78 169.41 120.03 102.13 232.038 373.85 308.03 739.66 400.06 264.04 586.30 168.9342 275.29 225.93

11.85 7.5 7.11 7.00 6.523 3.49 8.36 8.65 7.1 5.55 9.52 10.2 6.875 9.05 6.77 8.39 1.50915

280 733 1356 588 89.3 303.5 460 272 430 d ⫺3 326 550 d 442 206 579 834 ⬎400 340 632 448

1245 3230 1550 1457 820 720 d 130 826 823 d 450 1080 ⫺O2, 875

d 1367 73.5

ca. ⫺2 2.8517 1.635

11.7 4.59 6.1 6.00 10.0 2.77 9.32 7.971

38.0 ⫺40.8 ⫺148.8 ⫺165 1750 770 1110 570 d 630, ThO2 3390 anhyd 400 1545 824 1158

209 d 125 ⫺52.2 ⫺10.6 4788 921 1680 837 4400 1950 1490 2230

hyd aq; s HI, alkali; sl s acet s HCl, HF, NaOH s acids v s aq s aq i aq; s HNO3 0.0520 aq; s alc 4.1 g/100 mL20 aq; i alc 0.3320 aq; i alc 16.8 g/100 mL28 aq; s alc, acid s eth; sl s alc; d aq 78.6%15 aq d aq i aq, alc; s KI 9.55 g/100 mL20 aq; i alc v s aq; s acid, alc i aq; d by HCl, H2SO4 2.8 g/100 mL20 aq; i alc, eth i aq, acid 4.87 g/100 mL20 aq 0.0220 aq; s mineral acids d aq; s eth d aq; s alc, CS2, eth s aq, eth, CS2 hyd aq; s bz, chl, CS2 hyd aq s acids s aq, alc s acids hyd aq 191 g/100 mL20 aq; v s alc s hot H2SO4 1.57 g/100 mL25 aq s acids s aq, alc s H2SO4

INTERACTIVE

PSBr3 PSCl3 PSF3 S " SF2 Th ThCl4 ThF4 ThI4 Th(NO3)4 ThO2 Th(SO4)2 · 9H2O Tm TmCl3 TmF3

5.05 5.9 8.23 4.35

RIGHT

635.22 159.60 158.9254 265.28 453.03 204.383 284.29 468.78 239.84 230.40 249.44 223.38 261.38 331.29 266.39 424.77 456.77 551.73 487.73 504.83 440.83 114.98 116.16

(McGHP)

TeI4 TeO2 Tb TbCl3 Tb(NO3)3 · 6H2O Tl TlBr Tl2CO3 TlCl TlCN TlOC2H5 TlF TlF3 TlI TlNO3 Tl2O Tl2O3 Tl2SeO4 Tl2Se Tl2SO4 Tl2S S " CCl (SCN)2

DEAN #37261

3.55

(IV) iodide (IV) oxide Terbium chloride nitrate 6-water Thallium (I) bromide (I) carbonate (I) chloride (I) cyanide (I) ethoxide (I) fluoride (III) fluoride (I) iodide (rhombic) (I) nitrate (I) oxide (III) oxide (hexagonal) (I) selenate(VI) (I) selenide (I) sulfate (I) sulfide Thiocarbonyl chloride Thiocyanogen Thionyl, see Sulfinyl Thiophosphoryl tribromide trichloride (alpha) trifluoride Thiosulfinyl difluoride Thorium chloride fluoride iodide nitrate oxide sulfate 9-water Thullium chloride fluoride

top of page

short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Name

Formula

Formula weight

Density 7.265 2.31 5.12 3.34 3.90 2.234 4.57 4.78 4.21 5.285 4.46 3.56 6.45 6.95 6.179 4.15 5.08 4.5

(II) telluride Titanium (hexagonal) (III) bromide (IV) bromide (II) chloride (III) chloride (IV) chloride dihydride (IV) fluoride (IV) iodide (IV) isopropoxide (II) oxide

SnTe Ti TiBr3 TiBr4 TiCl2 TiCl3 TiCl4 TiH2 TiF4 TiI4 Ti[OCH(CH3)2]4 TiO

246.31 47.867 287.58 367.48 118.77 154.23 189.68 49.88 123.86 555.49 284.22 63.87

6.5 4.506 4.24 3.37 3.13 2.64 1.73 3.752 2.798 4.3 0.971120 4 4.95

231.928 182.5 215 31 246.9 ⫺3.3 213

2602 240 639 205 623 114.1 850 subl 705

320 143 280 d to SnO2, 300 1630 861 to SnO2, 378 880 d 600

714 364

790 1668 39 1035 425 d ⫺25 d 450 ⬎400 150 ⬃20 1750

1210

3287 subl 794 230 1500

s conc HCl, hot H2SO4 d aq; s dilute HCl 85 g/100 mL0 aq; s alc, eth v a (hyd) aq; s acet, alc 84 g/100 mL0 aq; s acet, alc, eth s aq (hyd), alc, acet, bz, eth 30% aq hyd aq s aq 0.9820 aq (d); s bz, chl, alk Cl⫺ or I⫺ hyd aq; s alc, bz, chl, eth, CCl4, CS2 s dilute HCl s acids, conc KOH s hot conc KOH (slow) s aqua regia, alkali sulfides 18.9 g/100 mL20 aq; s dilute H2SO4 s conc HCl, hot conc H2SO4 s aq reg, alkali hydroxides & sulfides i aq s hot acid, HF

136.4

hyd aq; 187 g/100 mL abs alc d aq; s alc s aq (heat evolved), alc s cold aq, alc

subl 285.5 377 220 3660

s aq (slow hyd); s alc, pyr s dry nonpolar solvents d aq; s bz, chl, eth s H2SO4

INTERACTIVE

118.710 236.80 278.52 438.33 189.61 260.52 156.71 194.70 323.92 372.52 626.33 206.73 134.71 150.71 197.67 214.77 150.78 182.84

Solubility in 100 parts solvent

LEFT

Sn Sn(C2H3O2)2 SnBr2 SnBr4 SnCl2 SnCl4 SnF2 SnF4 Sn[ZrF6] SnI2 SnI4 SnC2O4 SnO SnO2 SnSe SnSO4 SnS SnS2

Boiling point, ⬚C

(McGHP)

3.56

Tin (white) (II) acetate (II) bromide (IV) bromide (II) chloride (IV) chloride (II) fluoride (IV) fluoride hexafluorozirconate (II) iodide (IV) iodide (II) oxalate (II) oxide (IV) oxide (II) selenide (II) sulfate (II) sulfide (IV) sulfide

Melting point, ⬚C

top of page

short standard

base of DF

WBr5 WBr6 WCl5 WCl6 WCl2O2 WF6 WO2 WO3 WS2 WCl4O WF4O U UBr4 UCl3 UCl4 UCl5 UCl6 UF4 UF6 UH3 UI4 UO2 UO3 U3O8 UO4 · 2H2O

583.36 663.26 361.10 396.56 286.74 297.83 215.84 231.84 247.97 341.65 275.83 238.0289 557.65 344.39 379.84 415.29 450.75 314.02 352.02 241.05 745.65 270.03 286.03 842.08 338.06

Uranyl(VI) acetate 2-water chloride fluoride nitrate 6-water sulfate 3-water

UO2(C2H3O2)2 · 2H2O UO2Cl2 UO2F2 UO2(NO3)2 · 6H2O UO2SO4 · 3H2O

422.13 340.93 308.03 502.13 420.14

19.25

6.9 3.875 3.52 4.67 3.441 10.8 7.16 7.6 11.92 5.07 19.1 5.55 5.51 4.725 3.6 6.70 5.09 11.1 5.6 10.97 7.29 8.38

2.893 5.43 6.37 2.807 3.28

1842 1843

3387

5900

286 309 242 279 265 2.3 1550 1472 d 1250 211 106 1135 519 837 590 287 177 1036 64.0

333 subl 327 286 347 d 369 17.5 d 1724 1837

506 2827 d 1300 d 1300 to UO2 d 90– 195 to U2O7 (slow) anhyd 110 577 d 300 60 d 100

227 186 4131 777 1657 790 527 392 1417 subl 56.5 757

d ⬎200 to UO2 d 275

d 118

s H2SO4, hot HF s HF, hot conc H2SO4 d aq s dilute HCl, dilute H2SO4 s HNO3 ⫹ HF, fusion NaOH ⫹ NaNO3 hyd aq; s chl, eth hyd aq; s eth CS2 hyd aq hyd aq; s CS2, CCl4 hyd aq; s HCl hyd aq; s anhyd HF s acids, KOH i aq; s hot alkali s HNO3 ⫹ HF hyd aq s acid v s aq v s aq v s aq (d); s polar org solvents d aq; s CS2 hyd aq; s chl s conc acids (d); alk (d) hyd aq; s chl, CCl4 i aq s aq s conc HNO3 i aq; s HCl, HNO3 s HNO3 d by HCl

INTERACTIVE

(V) bromide (VI) bromide (V) chloride (VI) chloride dichloride dioxide (VI) fluoride (IV) oxide (VI) oxide (IV) sulfide tetrachloride oxide tetrafluoride oxide Uranium (IV) bromide (III) chloride (IV) chloride (V) chloride (VI) chloride (IV) fluoride (VI) fluoride (III) hydride (IV) iodide (IV) oxide (pitchblende) (VI) oxide octaoxide [(V,VI) oxide] peroxide 2-water

4.486 4.23

RIGHT

143.73 79.87 159.94 383.93 183.84

(McGHP)

Ti2O3 TiO2 TiOSO4 Ti2(SO4)3 W

DEAN #37261

3.57

(III) oxide (IV) oxide (rutile) oxide sulfate (III) sulfate Tungsten

7.7 g/100 mL15 aq; sl s alc 320 g/100 mL18 aq; s acet, alc v s aq 155 g/100 mL20 aq; v s alc, eth g/100 mL: 21 aq, 4 alc

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short standard

base of DF

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

Formula

Formula weight

Density

Melting point, ⬚C

3.58

50.9415 192.75 137.86 107.94 126.94

6.1119 1.82 2.88 3.363 3.15

(V) fluoride (II) oxide (III) oxide (IV) oxide (V) oxide (IV) oxide sulfate (III) sulfate (III) sulfide Xenon difluoride hexafluoride tetrafluoride trioxide Ytterbium (II) chloride (III) chloride 6-water (III) fluoride (III) nitrate 4-water (III) oxide (III) sulfate 8-water Yttrium chloride fluoride

VF5 VO V2O3 VO2 V2O5 VOSO4 V2(SO4)3 V2S3 Xe XeF XeF6 XeF4 XeO3 Yb YbCl2 YbCl3 · 6H2O YbF3 Yb(NO3)3 · 4H2O Yb2O3 Yb2(SO4)3 · 8H2O Y YCl3 YF3

145.93 66.94 149.88 82.94 181.88 163.00 390.07 198.08 131.29 169.29 245.28 207.28 179.29 173.04 243.95 387.49 230.04 431.12 394.08 778.39 88.9059 195.26 145.90

2.50 5.76 4.87 4.34 3.35

1917 ⫺25.7 disprop 384 ⬇1400 subl 120 (vac) & disprop 19.5 1790 1940 1967 670

4.72 5.761 g/L 4.32 3.56 4.04 4.55 6.90 5.27 2.57 8.17

410 (vac) d 600 ⫺111.8 129.0 49.5 117.1 explodes 25 819 721 anhyd 180 1157

9.18 3.3 4.472 2.61 4.0

3421 148 subl 800

48

d 1800

⫺108.04 subl 114.3 75.6 subl 115.7 1196 1930 mp: 865 2230

2435 1522 721 1152

3345 1510 2230

s HF, HNO3, hot H2SO4, aq reg hyd aq; s nonpolar solvents hyd (slow) aq; s abs alc, HOAc i almost all organic solvents s aq, acet, HOAc hyd aq; v s anhyd HF, acet, alc s HCl sl s acids s acids, alkalis 0.07 aq; s conc acids, alkalis s aq s (slow) aq, HNO3 s hot acids, alkali sulfides 10.8 mL/100 mL20 aq 2.5 g/100 mL0 aq hyd aq hyd aq; s F3CCOOH s aq giving xenic acid s acids s aq v s aq s H2SO4 s aq s dilute acids 34.8 g/100 mL20 aq s hot water (d) 79 g/100 mL20 aq; s alc s conc acids (d)

INTERACTIVE

V VCl4 VCl2O VF3 VF4

Solubility in 100 parts solvent

LEFT

Vanadium (IV) chloride dichloride oxide (III) fluoride (IV) fluoride

Boiling point, ⬚C

(McGHP)

Name

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short standard

base of DF

4300 d ⬎1000 907

3.33 4.5

394

697

carbonate chloride

ZnCO3 ZnCl2

125.40 136.29

4.4 2.907

⫺CO2, 300 290

732

chromate(VI) cyanide fluoride hexafluorosilicate 6-water iodate iodide nitrate 6-water oxide peroxide 1,4-phenolsulfonate 8-water phosphate(V) phosphide propionate selenide silicate(2⫺) stearate sulfate sulfate 7-water sulfide (wirzite) telluride thiocyanate

ZnCrO4 Zn(CN)2 ZnF2 Zn[SiF6] · 6H2O Zn(IO3)2 ZnI2 Zn(NO3)2 · 6H2O ZnO ZnO2 Zn[C6H4(OH)SO3]2 · 8H2O

181.39 117.43 103.39 315.56 415.20 319.20 297.49 81.39 97.39 555.84

3.40 1.852 4.9 2.104 5.063 4.74 2.067 5.60 1.57

Zn3(PO4)2 Zn3P2 Zn(C3H5O2)2 ZnSe Zn2SiO4 Zn(C18H35O2)2 ZnSO4 ZnSO4 · 7H2O ZnS ZnTe Zn(SCN)2

386.11 258.12 211.53 144.35 222.86 632.34 161.45 287.56 97.46 192.99 181.56

3.998 4.55

900 420

5.65 4.10 1.095 3.8 1.97 4.09 6.34

⬎1100 1512 130 680 d anhyd 280 1722 1239

3.59

d 800 872 d 100 d 446 ⫺6H2O, 131 1975 d ⬎150 anhyd 120

1500

625 d

explodes 212

1100

d ⬎500

171 g/100 mL20 aq s acids 9.6 g/100 mL20 aq i aq; s acids, alkalis (slow) g/100 mL: 41.620 aq, 3.3 alc s acids s acids and alkalis g/100 mL: 47125 aq, 200 alc; s KOH, eth 0.0225 aq; s acids, KOH, NH4 salts g/100 ml: 39520 aq, 77 alc, 50 glyc; v s acet s acids 0.05818 aq; s acids, KCN, KOH s HNO3, HCl, NH4OH v s aq 0.8720 aq; s HNO3, KOH g/100 mL: 33220 aq, 50 glyc; v s alc 146 g/100 mL0 aq; v s alc i aq; s acids, KOH, NH4OH d (slow) aq; s dilute acids (d) g/100 mL: 63 aq, 56 alc s acids, NH4OH d aq, HCl (viol); s bz, CS2 32%15 aq; 2.8%15 alc d dilute HNO3 i aq or dilute acids d dil acids; s bz; i aq, alc, eth 53.8%20 aq g/100 mL: 167 aq, 40 glyc; i alc i aq; s dilute mineral acids d (slow) aq or dilute HCl 0.14 aq; s alc

INTERACTIVE

⫺3H2O, 100 2440 anhyd 400 419.527 237 d

RIGHT

2.68 5.03 2.56 7.14 1.735

(McGHP)

383.01 225.81 610.12 65.39 219.51 279.23 618.13 225.20

DEAN #37261

Y(NO3)3 · 6H2O Y2O3 Y2(SO4)3 · 8H2O Zn Zn(C2H3O2)2 · 2H2O Zn(AsO2)2 Zn3(AsO4)2 · 8H2O ZnBr2

nitrate 6-water oxide sulfate 8-water Zinc acetate dihydrate arsenate(III)(1⫺) arsenate(V)(3⫺) 8-water bromide

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short standard

base of DF

Name Zirconium

Formula Zr

Formula weight 91.224

Density

Melting point, ⬚C

Boiling point, ⬚C

1852

3577

3.98 6.73 3.6 2.80 6.17 1.91 5.61 4.436 3.25

450 3532 727 437 (25 atm) 3245 anhyd 210

subl 357 5100 1292 subl 334 d 4193 d 410

932tp to ZrO2, 500 499 (sealed tube) d 100 2678 d 1540 to ZrO2 ⫹ SiO2 anhyd 380

subl 912

(IV) bromide carbide (II) chloride (IV) chloride diboride dichloride oxide 8-water dihydride (IV) fluoride (IV) hydroxide (IV) iodide

ZrBr4 ZrC ZrCl2 ZrCl4 ZrB2 ZrCl2O · 8H2O ZrH2 ZrF4 Zr(OH)4 ZrI4

410.84 103.23 162.13 233.03 112.85 322.25 93.24 167.22 159.25 598.84

(IV) nitrate 5-water (IV) oxide (IV) silicate(4⫺)

Zr(NO3)4 · 5H2O ZrO2 ZrSiO4

429.32 123.22 183.31

5.68 4.56

sulfate 4-water

Zr(SO4)2 · 4H2O

355.41

2.80

subl 432.5

4300

s aq reg, HF, hot H3PO4, fusion with KOH ⫹ KNO3

(McGHP)

3.60

6.52

Solubility in 100 parts solvent

DEAN #37261

TABLE 3.2 Physical Constants of Inorganic Compounds (Continued)

sl s conc H2SO4 d aq hyd aq to ZrCl2O; s alc, eth v s aq, alc i aq 1.32 g/100 mL20 aq s mineral acids s aq (d), eth v s aq; s alc s hot H2SO4, HF (slow) unaffected by aqueous reagents 52.5 g/100 g aqueous solution

LEFT INTERACTIVE

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short standard

base of DF

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

INORGANIC CHEMISTRY

3.61

cap height base of text

TABLE 3.3 Synonyms and Mineral Names Acanthite, see Silver sulfide Alabandite, see Manganese sulfide Alamosite, see Lead(II) silicate(2⫺) Altaite, see Lead telluride Alumina, see Aluminum oxide Alundum, see Aluminum oxide Alunogenite, see Aluminum sulfate 18-water Amphibole, see Magnesium silicate(2⫺) Andalusite, see Aluminum silicon oxide (l/1) Anglesite, see Lead sulfate Anhydrite, see Calcium sulfate Anhydrone, see Magnesium perchlorate Aragonite, see Calcium carbonate Arcanite, see Potassium sulfate Argentite, see Silver sulfide Argol, see Potassium hydrogen tartrate Arkansite, see Titanium(IV) oxide Arsenolite, see Arsenic(III) oxide dimer Arsine, see Arsenic hydride Auric and aurous, see under Gold Azoimide, see Hydrogen azide Azurite, see Copper(II) carbonate— dihydroxide (2/1) Baddeleyite, see Zirconium(IV) oxide Baking soda, see Sodium hydrogen carbonate Barite (barytes), see Barium sulfate Bieberite, see Cobalt sulfate 7-water Bismuthine, see Bismuth hydride Bismuthinite, see Bismuth sulfide Bleaching powder, see Calcium hydrochlorite Bleaching solution, see Sodium hydrochlorite Blue copperas, see Copper(II) sulfate 7-water Boracic acid, see Hydrogen borate Borax, see Sodium tetraborate 10-water Braunite, see Manganese(III) oxide Brimstone, see Sulfur Bromellite, see Beryllium oxide Bromosulfonic acid, see Hydrogen bromosulfate Bromyrite, see Silver bromide Brookite, see Titanium(IV) oxide Brucite, see Magnesium hydroxide Bunsenite, see Nickel oxide Cacodylate, see Sodium dimethylarsonate 3-water Caesium, see under Cesium Calamine, see Zinc carbonate Calcia, see Calcium oxide Calcite, see Calcium carbonate Calomel, see Mercury(I) chloride Caro’s acid, see Hydrogen peroxosulfate Cassiopeium, see Lutetium Cassiterite, see Tin(IV) oxide Caustic potash, see Potassium hydroxide Caustic soda, see Sodium hydroxide Celestite, see Strontium sulfate

top of rh base of rh

Cementite, see tri-Iron carbide Cerargyrite, see Silver chloride Cerussite, see Lead carbonate Chalcanthite, see Copper(II) sulfate 5-water Chalcocite, see Copper(I) sulfide Chalk, see Calcium carbonate Chile nitre, see Sodium nitrate Chile saltpeter, see Sodium nitrate Chloromagnesite, see Magnesium chloride Chlorosulfonic acid, see Hydrogen chlorosulfate Cinnabar, see Mercury(II) sulfide Claudetite, see Arsenic(III) oxide dimer Clausthalite, see Lead selenide Clinoenstatite, see Magnesium silicate(2⫺) Columbium, see under Niobium Corrosive sublimate, see Mercury(II) chloride Corundum, see Aluminum oxide Cotunite, see Lead chloride Covellite, see Copper(II) sulfide Cream of tartar, see Potassium hydrogen tartrate Crocoite, see Lead chromate(VI)(2⫺) Cryolite, see Sodium hexafluoroaluminate Cryptohalite, see Ammonium hexafluorosilicate Cupric and cuprous, see under Copper Cuprite, see Copper(I) oxide Dakin’s solution, see Sodium hypochlorite Dehydrite, see Magnesium perchlorate Dental gas, see Nitrogen(I) oxide Diamond, see Carbon Dichlorodisulfane, see di-Sulfur dichloride Diuretic salt, see Potassium acetate Dolomite, see Calcium magnesium carbonate (1/1) Dry ice, see Carbon dioxide (solid) Enstatite, see Magnesium silicate(2⫺) Epsom salts, see Magnesium sulfate 7-water Epsomite, see Magnesium sulfate 7-water Eriochalcite, see Copper(II) chloride Fayalite, see Iron(II) silicate(4⫺) Ferric and ferrous, see under Iron Fluorine oxide, see Oxygen difluoride Fluoristan, see Tin(II) fluoride Fluorite, see Calcium fluoride Fluorosulfonic acid, see Hydrogen fluorosulfate Fluorspar, see Calcium fluoride Forsterite, see Magnesium silicate(4⫺) Freezing salt, see Sodium chloride Fulminating mercury, see Mercury fulminate Galena, see Lead sulfite Glauber’s salt, see Sodium sulfate 10-water Goethite, see Iron(II) hydroxide oxide Goslarite, see Zinc sulfate 7-water Graham’s salt, see Sodium phosphate(1⫺) Graphite, see Carbon

short standard long

DEAN #37261

LEFT

(McGHP)

3.62

INTERACTIVE

SECTION 3

TABLE 3.3 Synonyms and Mineral Names (Continued) Greenockite, see Cadmium sulfide Gruenerite, see Iron(II) silicate(2⫺) Guanajuatite, see Bismuth selenide Gypsum, see Calcium sulfate 2-water Halite, see Sodium chloride Hausmannite, see Manganese(II,IV) oxide Heavy hydrogen, see Hydrogen[2H] or name followed by -d Heavy water, see Hydrogen[2H] oxide Heazlewoodite, see tri-Nickel disulfide Hematite, see Iron(III) oxide Hermannite, see Manganese silicate Hessite, see Silver telluride Hieratite, see Potassium hexafluorosilicate Hydroazoic acid, see Hydrogen azide Hydrophilite, see Calcium chloride Hydrosulfite, see Sodium dithionate(III) Hypo (photographic), see Sodium thiosulfate 5-water Hypophosphite, see under Phosphinate Ice, see Hydrogen oxide (solid) Iceland spar, see Calcium carbonate Iodyrite, see Silver iodide Jeweler’s borax, see Sodium tetraborate 10-water Jeweler’s rouge, see Iron(III) oxide Kalinite, see Aluminum potassium bis(sulfate) Kernite, see Sodium tetraborate Kyanite, see Aluminum silicon oxide (1/1) Laughing gas, see Nitrogen(I) oxide Lautarite, see Calcium iodate Lawrencite, see Iron(II) chloride Lechatelierite, see Silicon dioxide Lime, see Calcium oxide Litharge, see Lead(II) oxide Lithium aluminum hydride, see Lithium tetrahydridoaluminate Lodestone, see Iron(II,III) oxide Lunar caustic, see Silver nitrate Lye, see Sodium hydroxide Magnesia, see Magnesium oxide Magnesite, see Magnesium carbonate Magnetite, see Iron(II,III) oxide Malachite, see Copper carbonate dihydroxide Manganosite, see Manganese(II) oxide Marcasite, see Iron disulfide Marshite, see Copper(I) iodide Mascagnite, see Ammonium sulfate Massicotite, see Lead oxide Mercuric and mercurous, see under Mercury Metacinnabar, see Mercury(II) sulfide Millerite, see Nickel sulfide Mirabilite, see Sodium sulfate Mohr’s salt, see Ammonium iron(II) sulfate 6-water

top of rh base of rh cap height base of text

Moissanite, see Silicon carbide Molybdenite, see Molybdenum disulfide Molybdite, see Molybdenum(VI) oxide Molysite, see Iron(III) chloride Montroydite, see Mercury(II) oxide Morenosite, see Nickel sulfate 7-water Mosaic gold, see Tin disulfide Muriatic acid, see Hydrogen chloride, aqueous solutions Nantokite, see Copper(I) chloride Natron, see Sodium carbonate Naumannite, see Silver selenide Neutral verdigris, see Copper(II) acetate Nitre (niter), see Potassium nitrate Nitric oxide, see Nitrogen(II) oxide Nitrobarite, see Barium nitrate Nitromagnesite, see Magnesium nitrate 6-water Nitroprusside, see Sodium pentacyanonitrosylferrate(II) 2-water Oldhamite, see Calcium sulfide Opal, see Silicon dioxide Orpiment, see Arsenic trisulfide Oxygen powder, see Sodium peroxide Paris green, see Copper acetate arsenate(III) (1/3) Pawellite, see Calcium molybdate(VI)(2⫺) Pearl ash, see Potassium carbonate Perborax, see Sodium peroxoborate Periclase, see Magnesium oxide Persulfate, see Peroxodisulfate Phosgene, see Carbonyl chloride Phosphine, see Hydrogen phosphide Pickling acid, see Hydrogen sulfate Pitchblende, see Uranium(IV) oxide Plaster of Paris, see Calcium sulfate hemihydrate Plattnerite, see Lead(IV) oxide Polianite, see Manganese(IV) oxide Polishing powder, see Silicon dioxide Potash, see Potassium carbonate Potassium acid phthalate, see Potassium hydrogen phthalate Prussic acid, see Hydrogen cyanide Pyrite, see Iron disulfide Pyrochroite, see Manganese(II) hydroxide Pyrohytpophosphite, see diphosphate(IV) Pyrolusite, see Manganese(IV) oxide Pyrophanite, see Manganese titanate(IV)(2⫺) Pyrophosphate, see Diphosphate(V) Pyrosulfuric acid, see Hydrogen disulfate Quartz, see Silicon dioxide Quicksilver, see Mercury Realgar, see di-Arsenic disulfide Red lead, see Lead(II,IV) oxide Rhodochrosite, see Manganese carbonate

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

INORGANIC CHEMISTRY

3.63

TABLE 3.3 Synonyms and Mineral Names (Continued) Rhodonite, see Manganese silicate(1⫺) Rochelle salt, see Potassium sodium tartrate 4-water Rock crystal, see Silicon dioxide Rutile, see Titanium(IV) oxide Sal soda, see Sodium carbonate 10-water Saltpeter, see Potassium nitrate Scacchite, see Manganese chloride Scheelite, see Calcium tungstate(VI)(2⫺) Sellaite, see Magnesium fluoride Senarmontite, see Antimony(III) oxide Siderite, see Iron(II) carbonate Siderotil, see Iron(II) sulfate 5-water Silica, see Silicon dioxide Silicotungstic acid, see Silicon oxide— tungsten oxide— water (l/12/26) Sillimanite, see Aluminum silicon oxide (l/1) Smithsonite, see Zinc carbonate Soda ash, see Sodium carbonate Spelter, see Zinc metal Sphalerite, see Zinc sulfide Spherocobaltite, see Cobalt(II) carbonate Spinel, see Magnesium aluminate(2⫺) Stannic and stannous, see under Tin Stibine, see Antimony hydride Stibnite, see Antimony(III) sulfide Stolzite, see Lead tungstate(VI)(2⫺) Strengite, see Iron(III) phosphate Strontianite, see Strontium carbonate Sugar of lead, see Lead acetate Sulfamate, see Amidosulfate Sulphate, see Sulfate Sulfurated lime, see Calcium sulfide Sulfuretted hydrogen, see Hydrogen sulfide Sulphur, see Sulfur Sulfuryl, see Sulfonyl Sycoporite, see Cobalt sulfide

top of rh base of rh cap height base of text

Sylvite, see Potassium chloride Szmikite, see Manganese(II) sulfate hydrate Tarapacaite, see Potassium chromate(VI) Tellurite, see Tellurium dioxide Tenorite, see Copper(II) oxide Tephroite, see Manganese silicate(1⫺) Thenardite, see Sodium sulfate Thionyl, see Sulfinyl Thorianite, see Thorium dioxide Topaz, see Aluminum hexafluorosilicate Tridymite, see Silicon dioxide Troilite, see Iron(II) sulfide Trona, see Sodium carbonate— hydrogen carbonate dihydrate Tschermigite, see Aluminum ammonium bis(sulfate) Tungstenite, see Tungsten disulfide Tungstite, see Hydrogen tungstate Uraninite, see Uranium(IV) oxide Valentinite, see Antimony(III) oxide Verdigris, see Copper acetate hydrate Vermillion, see Mercury(II) sulfide Villiaumite, see Sodium fluoride Vitamin B3, see Calcium (⫹)pantothenate Washing soda, see Sodium carbonate 10-water Whitlockite, see Calcium phosphate Willemite, see Zinc silicate(4⫺) Wolfram, see Tungsten Wuestite, see Iron(II) oxide Wulfenite, see Lead molybdate(VI)(2⫺) Wurtzite, see Zinc sulfide Zincite, see Zinc oxide Zincosite, see Zinc sulfate Zincspar, see Zinc carbonate Zirconia, see Zirconium oxide

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

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SECTION 4

PROPERTIES OF ATOMS, RADICALS, AND BONDS 4.1

ELEMENTS Table 4.1 Electronic Configuration and Properties of the Elements 4.2 IONIZATION ENERGY Table 4.2 Ionization Energy of the Elements Table 4.3 Ionization Energy of Molecular and Radical Species 4.3 ELECTRON AFFINITY Table 4.4 Electron Affinities of Elements, Molecules, and Radicals 4.4 ELECTRONEGATIVITY Table 4.5 Electronegativities of the Elements 4.5 BOND LENGTHS AND STRENGTHS 4.5.1 Atom Radius Table 4.6 Atom Radii and Effective Ionic Radii of Elements 4.5.2 Ionic Radii 4.5.3 Covalent Radii Table 4.7 Covalent Radii for Atoms Table 4.8 Octahedral Covalent Radii for CN ⴝ 6 Table 4.9 Bond Lengths between Carbon and Other Elements Table 4.10 Bond Lengths between Elements Other than Carbon Table 4.11 Bond Dissociation Energies 4.6 BOND AND GROUP DIPOLE MOMENTS Table 4.12 Bond Dipole Moments Table 4.13 Group Dipole Moments 4.7 MOLECULAR GEOMETRY Table 4.14 Spatial Orientation of Common Hybrid Bonds Figure 4.1 Crystal Lattice Types Table 4.15 Crystal Structure 4.8 NUCLIDES Table 4.16 Table of Nuclides 4.9 WORK FUNCTION Table 4.17 Work Functions of the Elements 4.10 RELATIVE ABUNDANCES OF NATURALLY OCCURRING ISOTOPES Table 4.18 Relative Abundances of Naturally Occurring Isotopes

4.1

4.1 4.2 4.6 4.6 4.8 4.24 4.24 4.28 4.29 4.29 4.29 4.30 4.34 4.35 4.35 4.36 4.36 4.39 4.41 4.53 4.53 4.54 4.56 4.56 4.57 4.58 4.58 4.58 4.80 4.80 4.81 4.81

ELEMENTS

The electronic configuration for an element’s ground state (Table 4.1) is a shorthand representation giving the number of electrons (superscript) found in each of the allowed sublevels (s, p, d, f) above a noble gas core (indicated by brackets). In addition, values for the thermal conductivity, the electrical resistance, and the coefficient of linear thermal expansion are included. 4.1

short standard base of DF

Name

4.2

Electronic configuration

Ac Al Am Sb Ar As At Ba Bk Be Bi B Br Cd Ca Cf C

89 13 95 51 18 33 85 56 97 4 83 5 35 48 20 98 6

[Rn] 6d 2 7s [Ne] 3s2 3p [Rn] 5f 7 7s2 [Kr] 4d10 5s2 5p3 [Ne] 3s2 3p6 [Ar] 3d10 4s2 4p3 [Xe] 4f 14 5d10 6s2 6p5 [Xe] 6s2 [Rn] 5f 8 6d 7s2 [He] 2s2 [Xe] 4f14 5d10 6s2 6p3 [He] 2s2 2p [Ar] 3d10 4s2 4p5 [Kr] 4d10 5s2 [Ar] 4s2 [Rn] 5f 10 7s2 [He] 2s2 2p2

[Xe] 4f 5d 6s2 [Xe] 6s [Ne] 3s2 3p5 [Ar] 3d5 4s [Ar] 3d7 4s2 [Ar] 3d10 4s [Rn] 5f 7 6d 7s2 [Xe] 4f 10 6s2 [Rn] 5f 11 7s2 [Xe] 4f 14 6s2 [Xe] 4f 7 6s2

12 237 10 24.4 0.017 72 50.2 1.7 18.4 10 200 7.97 27.4 0.122 96.6 201

3.56 129 1.5 ⫻ 1012 7.8 ⫻ 1018 7.27 (22⬚C) 3.36

1.59 900– 2320 119– 165 11.3 35.9 0.0089 93.9 100 401

0.8 1375 82.8 (␤, hex) 20.5 ⬎109 12.5 6.24 1.678

2.6548 41.7

Coefficient of linear thermal expansion (25⬚C), m · m⫺1(⫻ 106 )

23.1 11.0

33.3 33.2

20.6 11.3 13.4 5– 7 30.8 22.3

6.3

4.9 13.0 16.5

10.7

92.6

9.9

14.5 13.9

86.0 90.0

12.2 35.0

INTERACTIVE

58 55 17 24 27 29 96 66 99 68 63

Electrical resistivity, ␮⍀ · cm at 20⬚C

ROTATED

Ce Cs Cl Cr Co Cu Cm Dy Es Er Eu

Thermal conductivity, W · (m · K)⫺1 at 25⬚C

LEFT

Actinium Aluminum Americium Antimony (stibium) Argon Arsenic Astatine Barium Berkelium Beryllium Bismuth Boron Bromine Cadmium Calcium Californium Carbon (amorphous) (diamond) (graphite) Cerium Cesium Chlorine Chromium Cobalt Copper (cuprum) Curium Dysprosium Einsteinium Erbium Europium

Symbol

Atomic number

DEAN 37261 (McGHP)

TABLE 4.1 Electronic Configuration and Properties of the Elements

Palladium

Pd

46

[Rn] 5f 12 7s2 [He] 2s2 2p5 [Rn] 7s [Xe] 4f 7 5d 6s2 [Ar] 3d10 4s2 4p [Ar] 3d10 4s2 4p2 [Xe] 4f 14 5d10 6s [Xe] 4f 14 5d2 6s2 1s2 [Xe] 4f 11 6s2 1s [Kr] 4d10 5s2 5p [Kr] 4d10 5s2 5p5 [Xe] 4f 14 5d7 6s2 [Ar] 3d 6 4s2 [Ar] 3d10 4s2 4p6 [Xe] 5d 6s2 [Rn] 4f 14 6d 7s2 [Xe] 4f 14 5d10 6s2 6p2 1s2 2s [Xe] 4f 14 5d 6s2 [Ne] 3s2 [Ar] 3d 5 4s2 [Rn] 5f 13 7s2 [Xe] 4f 14 5d10 6s2 [Kr] 4d 5 5s [Xe] 4f 4 6s2 1s2 2s2 2p6 [Rn] 5f 4 6d 7s2 [Ar] 3d 8 4s2 [Kr] 4d4 5s 1s2 2s2 2p3 [Rn] 5f 14 7s2 [Xe] 4f 14 5d6 6s2 1s2 2s2 2p4 [Kr] 4d 10

0.0277 10.5 29.4(lq) 40.6(c) 60.2 318 23.0 0.1513 16.2 0.1805 81.8 449 147 80.4 9.43 13.4 35.3 84.8 16.4 156 7.81 8.30 138 16.5 0.0491 6.3 90.9 53.7 0.025 83 87.6 0.026 58 (g) 0.149 (lq) 71.8

131 25.795 (30⬚C) 53 000 2.214 33.1 81.4 8.37 1.3 ⫻ 1015 (0⬚C) 4.71 9.61

9.4 (100⬚C) 120 6.0 14.2 5.9 11.2 32.1 6.4 11.8

61.5

12.1

20.8 9.28 58.2 4.39 144

28.9 46 9.9 24.8 21.7

95.8(lq); 21(c) 5.34 64.3

4.8 9.6

122.0 (22⬚C) 6.93 15.2 (0⬚C)

13.4 7.3

8.12 (0⬚C)

5.1

10.54

ROTATED

100 9 87 64 31 32 79 72 2 67 1 49 53 77 26 36 57 103 82 3 71 12 25 101 80 42 60 10 93 28 41 7 102 76 8

RIGHT

Fm F Fr Gd Ga Ge Au Hf He Ho H In I Ir Fe Kr La Lr Pb Li Lu Mg Mn Md Hg Mo Nd Ne Np Ni Nb N No Os O

DEAN 37261 (McGHP)

4.3

Fermium Fluorine Francium Gadolinium Gallium Germanium Gold (aurum) Hafnium Helium Holmium Hydrogen Indium Iodine Iridium Iron (ferrum) Krypton Lanthanum Lawrencium Lead (plumbum) Lithium Lutetium Magnesium Manganese Mendelevium Mercury (hydrargyrum) Molybdenum Neodymium Neon Neptunium Nickel Niobium Nitrogen Nobelium Osmium Oxygen

11.8

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 4.1 Electronic Configuration and Properties of the Elements (Continued)

4.4

P Pt Pu Po K Pr Pm Pa Ra Rn Re Rh Rb Ru Sm Sc Se Si

15 78 94 84 19 59 61 91 88 86 75 45 37 44 62 21 34 14

[Ne] 3s2 3p3 [Xe] 4f 14 5d 9 6s [Rn] 5f 6 7s2 [Xe] 4f 14 5d 10 6s2 6p4 [Ar] 4s [Xe] 4f 3 6s2 [Xe] 4f 5 6s2 [Rn] 5f 2 6d 7s2 [Rn] 7s2 [Xe] 4f 14 5d10 6s2 6p6 [Xe] 5f 14 5d5 6s2 [Kr] 4d8 5s [Kr] 5s [Kr] 4d 7 5s [Xe] 4f 6 6s2 [Ar] 3d 4s2 [Ar] 3d10 4s2 4p4 [Ne] 3s2 3p2

0.236 17 71.6 6.74 0.2 102.5 12.5 17.9 47 18.6 0.003 61 48.0 150 58.2 117 13.3 15.8 0.519 149

Electrical resistivity, ␮⍀ · cm at 20⬚C 10 10.6 146.0 (0⬚C) 40.0 (0⬚C) alpha 7.2 70.0 64.0 (25⬚C) 19.1 (22⬚C) 100 19.3 4.33 (0⬚C) 12.8 7.1 (0⬚C) 94.0 56.2 1.2 (0⬚C) 105

Coefficient of linear thermal expansion (25⬚C), m · m⫺1(⫻ 106 )

8.8 46.7

6.7 est [11.]

6.2 8.2 6.4 12.7 10.2 37

INTERACTIVE

Phosphorus (white) Platinum Plutonium Polonium Potassium (kalium) Praseodymium Promethium Protactinium Radium Radon Rhenium Rhodium Rubidium Ruthenium Samarium Scandium Selenium (amorphous) Silicon

Thermal conductivity, W · (m · K)⫺1 at 25⬚C

ROTATED

Symbol

Electronic configuration

LEFT

Name

Atomic number

Ag Na Sr S Ta Tc Te Tb Tl Th Tm Sn Ti W U V Xe Yb Y Zn Zr

47 11 38 16 73 43 52 65 78 90 69 50 22 74 92 23 54 70 39 30 40

[Kr] 4d10 5s [Ne] 3s [Kr] 5s2 [Ne] 3s2 3p4 [Xe] 4f 14 5d 3 6s2 [Kr] 4d 5 5s2 [Kr] 4d10 5s2 5p4 [Xe] 4f 9 6s2 [Xe] 4f 14 5d10 6s2 6p [Rn] 6d 2 7s2 [Xe] 4f 13 6s2 [Kr] 4d10 5s2 5p2 [Ar] 3d 2 4s2 [Xe] 4f 14 5d 4 6s2 [Rn] 5f 3 6d 7s2 [Ar] 3d 3 4s2 [Kr] 4d10 5s2 5p6 [Xe] 4f 14 6s2 [Kr] 4d 5s2 [Ar] 3d10 4s2 [Kr] 4d2 5s2

429 142 35.4 0.205 57.5 50.6 1.97– 3.38 11.1 46.1 54.0 16.9 66.8 21.9 173 27.5 30.7 0.005 65 38.5 17.2 116 22.6

1.587 4.77 13.2 2 ⫻ 1023 13.5 22.6 (100⬚C) (5.8– 33) ⫻ 103 115 18 15.4 (22⬚C) 67.6 11.5 (0⬚C) 42.0 5.28 28.0 (0⬚C) 19.7 25 59.6 5.9 42.1

18.9 71 22.5 6.3

10.3 29.9 11.1 13.3 22.0 8.6 4.5 13.9 8.4

DEAN 37261 (McGHP)

Silver (argentum) Sodium (natrium) Strontium Sulfur (amorphous) Tantalum Technetium Tellurium Terbium Thallium Thorium Thullium Tin (stannum) Titanium Tungsten (wolframium) Uranium Vanadium Xenon Ytterbium Yttrium Zinc Zirconium

26.3 10.6 30.2 5.7

Source: Ho, C. Y., Powell, R. W., and Liley, P. E., J. Phys. Chem. Ref. Data 3:Suppl. 1 (1974), (thermal conductivity); Ho, C. Y., et al., J. Phys. Chem. Ref. Data, 12:183 (1983); 13:1069, 1097, 1131 (1984), (electrical resistivity); Touloukian, Y. S., Thermophysical Properties of Matter, Vol. 12, Thermal Expansion, Plenum, New York, 1975.

RIGHT ROTATED

4.5

INTERACTIVE

DEAN #37261

LEFT

(McGHP)

4.6

4.2

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

IONIZATION ENERGY

TABLE 4.2 Ionization Energy of the Elements The minimum amount of energy required to remove the least strongly bound electron from a gaseous atom (or ion) is called the ionization energy and is expressed in MJ · mol⫺1. Remember that 96.485 kJ ⫽ 1.000 eV ⫽ 23.0605 kcal. In Table 4.2 the successive stages of ionization are indicated by the heading of each column: I denotes first spectra arising from a neutral atom; viz., M(gas) : M⫹(gas) ⫹ e⫺ II, second spectra from singly ionized atoms, and so on for successive stages of ionization. Spectrum (in MJ · mol⫺1) At. no.

Element

I

II

III

IV

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

H He Li Be B C N O F Ne Na Mg Al Si P S Cl Ar K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Sc Br Kr Rb Sr Y Zr

1.312 2.372 0.520 0.899 0.801 1.086 1.402 1.314 1.681 2.081 0.496 0.738 0.578 0.786 1.012 1.000 1.251 1.521 0.419 0.590 0.631 0.658 0.650 0.653 0.717 0.759 0.758 0.737 0.745 0.906 0.579 0.762 0.947 0.941 1.140 1.351 0.403 0.549 0.616 0.660

5.251 7.298 1.757 2.427 2.353 2.856 3.388 3.374 3.952 4.562 1.451 1.817 1.577 1.903 2.251 2.297 2.666 3.051 1.145 1.235 1.310 1.414 1.592 1.509 1.561 1.646 1.753 1.958 1.733 1.979 1.537 1.798 2.045 2.10 2.350 2.632 1.064 1.181 1.267

11.815 14.849 3.660 4.620 4.578 5.300 6.147 6.122 6.912 7.733 2.745 3.231 2.912 3.361 3.822 3.931 4.411 4.912 2.389 2.652 2.828 2.987 3.248 2.957 3.232 3.393 3.555 3.833 2.963 3.302 2.735 2.974 3.47 3.565 3.9 4.138 1.980 2.218

21.007 25.027 6.223 7.475 7.469 8.408 9.370 9.543 10.540 11.577 4.355 4.956 4.564 5.158 5.771 5.877 6.474 7.089 4.175 4.507 4.743 4.94 5.63 4.95 5.30 5.536 5.73 6.2 4.410 4.837 4.143 4.56 5.07 5.08 5.5 5.96 3.313

V

VI

32.828 37.832 9.445 10.989 11.022 12.177 13.353 13.629 14.831 16.091 6.274 7.004 6.54 7.238 7.976 8.144 8.844 9.573 6.299 6.70 6.99 7.24 7.67 7.34 7.70 7.95

47.191 53.268 13.326 15.164 15.238 16.610 17.994 18.377 19.784 21.268 8.495 9.362 8.787 9.649 10.496 10.719 11.516 12.362 8.738 9.22 9.56 9.84 10.4 9.9 10.4

9.022 6.043 6.99 5.76 6.24 6.85 6.91 7.43 7.75

12.31 7.883 8.55 7.57 8.14 8.76 8.97

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

4.7

PROPERTIES OF ATOMS, RADICALS, AND BONDS

top of rh base of rh cap height base of text

TABLE 4.2 Ionization Energy of the Elements (Continued) Spectrum (in MJ · mol⫺1) At. no.

Element

I

II

III

IV

V

VI

41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91

Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe Cs Ba La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn Fr Ra Ac Th Pa

0.664 0.685 0.702 0.711 0.720 0.805 0.731 0.868 0.558 0.709 0.834 0.869 1.008 1.170 0.376 0.503 0.538 0.528 0.523 0.530 0.535 0.543 0.547 0.592 0.564 0.572 0.581 0.589 0.596 0.603 0.524 0.68 0.761 0.770 0.760 0.84 0.88 0.87 0.890 1.007 0.589 0.716 0.703 0.812

1.382 1.558 1.472 1.617 1.744 1.875 2.073 1.631 1.821 1.412 1.595 1.795 1.846 2.046 2.234 0.965 1.067 1.047 1.018 1.035 1.052 1.068 1.085 1.167 1.112 1.126 1.139 1.151 1.163 1.174 1.34 1.44

2.416 2.621 2.850 2.747 2.997 3.177 3.361 3.616 2.704 2.943 2.44 2.698 3.2 3.099

3.695 4.477

4.877 5.91

9.847 6.641

5.2 3.930 4.26 3.610

6.974 5.4 5.668

1.850 1.949 2.086 2.13 2.15 2.26 2.40 1.99 2.114 2.20 2.204 2.194 2.285 2.417 2.022 2.25

4.820 3.547 3.761 3.90 3.97 3.99 4.12 4.26 3.839 3.99 4.10 4.13 4.13 4.203 4.366 3.216

5.94 6.325 5.551

1.791 1.98 1.810 1.971 1.450 1.610

3.30 2.878 3.081 2.466

4.083 4.371

6.64 5.40

0.979 1.17 1.11

1.93

2.78

10.4 6.82

7.487

8.52

1.037 0.509 0.67 0.587 0.568

short standard long

DEAN #37261

LEFT

(McGHP)

4.8

INTERACTIVE

top of rh base of rh

SECTION 4

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TABLE 4.2 Ionization Energy of the Elements (Continued) Spectrum (in MJ · mol⫺1) At. no.

Element

I

92 93 94 95 96 97 98 99 100 101 102

U Np Pu Am Cm Bk Cf Es Fm Md No

0.598 0.605 0.585 0.578 0.581 0.601 0.608 0.619 0.627 0.635 0.642

II

III

IV

V

VI

Source: C. E. Moore, National Standard Reference Data Series 34, U.S. Government Printing Office, Washington, D.C., 1970; W. C. Martin, Zalubas, R., and Hagan, L., J. Phys. Chem. Reference Data, 3:771 (1974) and National Standard Reference Data Series, National Bureau of Standards (U.S.), No. 60 (1978) for the Rare Earth Elements; and Cohen, E. R. and Taylor, B. N., J. Phys. Chem. Reference Data, 17:1795 (1988).

TABLE 4.3 Ionization Energy of Molecular and Radical Species This table gives the first ionization potential in MJ · mol⫺1 and in electron volts. Also listed is the enthalpy of formation of the ion at 25⬚C (298 K). Compounds containing carbon Ionization energy Species Acenaphthene Acenaphthylene Acetaldehyde Acetamide Acetic acid Acetic anhydride Acetone Acetonitrile Acetophenone Acetyl chloride Acetyl fluoride Acetylene Allene Allyl alcohol Allylamine 3-Amino-1-propanol Aniline Anthracene Azoxybenzene Azulene Benzaldehyde Benzamide

In MJ · mol⫺1

In electron volts

0.741 0.793 0.98696(7) 0.931(3) 1.029(2) 0.965 0.9364 1.1766(5) 0.896(3) 1.047(5) 1.111(2) 1.1000(2) 0.935(1) 0.933(5) 0.845 0.87 0.7449(2) 0.719(3) 0.78 0.715(2) 0.916(2) 0.912

7.68 8.22(4) 10.2290(7) 9.65(3) 10.66(2) 10.0 9.705 12.194(5) 9.29(3) 10.85(5) 11.51(2) 11.400(2) 9.69(1) 9.67(5) 8.76 9.0 7.720(2) 7.45(3) 8.1 7.41(2) 9.49(2) 9.45

⌬f H (ion) in kJ · mol⫺1 896 1053 821 693 596 398 719 1252 810 804 667 1328 1126 808 891 651 832 949 1123 1004 878 811

short standard long

DEAN #37261

(McGHP)

RIGHT

PROPERTIES OF ATOMS, RADICALS, AND BONDS

INTERACTIVE

4.9

top of rh base of rh cap height base of text

TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species Benzene Benzenethiol Benzoic acid Benzonitrile Benzophenone p-Benzoquinone Benzoyl chloride Benzyl alcohol Benzylamine Biphenyl Bromoacetylene Bromobenzene Bromochlorodifluoromethane Bromochloromethane Bromodichloromethane Bromoethane Bromoethylene Bromomethane 1-Bromonaphthalene Bromopentafluorobenzene 1-Bromopropane 2-Bromopropane 3-Bromopropene p-Bromotoluene Bromotrichloromethane Bromotrifluoromethane 1,2-Butadiene 1,3-Butadiene Butanal Butanenitrile 2-Butanone trans-2-Butenal 1-Butene cis-2-Butene trans-2-Butene 1-Buten-3-yne Butyl acetate sec-Butyl acetate Butyl ethyl ether Butylbenzene sec-Butylbenzene tert-Butylbenzene Butylcyclohexane Butylcyclopentane p-tert-Butylphenol p-tert-Butyltoluene 1-Butyne 2-Butyne Camphor Caprolactam Carbazole

In MJ · mol⫺1

In electron volts

0.89212(2) 0.801(2) 0.914 0.928 0.873(5) 0.969(2) 0.920 0.82 0.834(5) 0.767(2) 0.995(2) 0.866(2) 1.141 1.039(1) 1.02 0.992 0.946(2) 1.0171(3) 0.781 0.923(2) 0.982(1) 0.972(1) 0.972(1) 0.837(1) 1.02 1.10 0.871 0.8750 0.949(2) 1.08 0.918(4) 0.939(1) 0.924(2) 0.8788(8) 0.8780(8) 0.924(2) 0.965 0.955 0.903 0.838(1) 0.837(1) 0.834(2) 0.908 0.960(3) 0.75 0.799 0.9821(5) 0.9226(5) 0.845(3) 0.875(2) 0.730(3)

9.2459(2) 8.30(2) 9.47 9.62 9.05(5) 10.04(18) 9.54 8.5 8.64(5) 7.95(2) 10.31(2) 8.98(2) 11.83 10.77(1) 10.6 10.28 9.80(2) 10.541(3) 8.09 9.57(2) 10.18(1) 10.07(1) 10.07(1) 8.67(1) 10.6 11.4 9.03 9.069 9.84(2) 11.2 9.51(4) 9.73(1) 9.58(2) 9.108(8) 9.100(8) 9.58(2) 10.0 9.90 9.36 8.69(1) 8.68(1) 8.64(2) 9.41 9.95(3) 7.8 8.28 10.178(5) 9.562(5) 8.76(3) 9.07(2) 7.57(3)

⌬f H (ion) in kJ · mol⫺1 975 913 620 1146 923 847 816 720 917 950 1242 971 702 1085 973 930 1025 979 956 212 898 874 1018 908 980 451 1034 985 742 1110 677 835 924 871 866 1230 479 453 610 826 820 812 695 793 552 745 1147 1068 577 629 961

short standard long

DEAN #37261

LEFT

(McGHP)

4.10

INTERACTIVE

top of rh base of rh

SECTION 4

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TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species Carbon Carbon (C2) Carbon dioxide Carbon monoxide Carbon oxyselenide Carbon oxysulfide Carbon sulfide Carbon sulfide (CS) Carbonyl fluoride Carbonyltrihydroboron (BH3CO) Chloroacetaldehyde Chloroacetic acid Chloroacetyl chloride Chloroacetylene m-Chloroaniline o-Chloroaniline p-Chloroaniline Chlorobenzene Chlorodibromomethane 1-Chloro-1,1-difluoroethane 1-Chloro-2,2-difluoroethylene Chlorodifluoromethane Chloroethane 2-Chloroethanol Chloroethylene Chlorofluoromethane Chloromethane Chloromethylene Chloromethylidine (CCl) 1-Chloronaphthalene m-Chloronitrobenzene p-Chloronitrobenzene Chloropentafluorobenzene Chloropentafluoroethane m-Chlorophenol p-Chlorophenol 1-Chloropropane 2-Chloropropane 3-Chloropropene m-Chlorotoluene o-Chlorotoluene p-Chlorotoluene Chlorotrifluoroethylene Chlorotrifluoromethane Chrysene Coronene m-Cresol o-Cresol p-Cresol cis-Crotonic acid trans-Crotonic acid

In MJ · mol⫺1 1.0865 1.188 1.3289(2) 1.35217 1.000(1) 1.07812(15) 0.97149(19) 1.093(1) 1.257 1.075(2) 1.011(3) 0.984 1.06 1.021(2) 0.781(10) 0.820 0.789 0.874(2) 0.1022(1) 1.156(1) 0.946(4) 1.18 1.058(2) 1.015 0.964(2) 1.130(1) 1.083(1) 0.949 0.86(2) 0.784 0.957(10) 0.961(10) 0.938(2) 1.22 0.835 0.834 1.044(3) 1.040(2) 0.96 0.852(2) 0.852(2) 0.838(2) 0.947 1.195 0.732 0.703 0.800 0.785 0.784 0.973 0.96

In electron volts 11.260 12.31 13.773(2) 14.0139 10.36(1) 11.1736(15) 10.0685(20) 11.33(1) 13.03 11.14(2) 10.48(3) 10.2 11.0 10.58(2) 8.09(10) 8.50 8.18 9.06(2) 10.59(1) 11.98(1) 9.80(4) 12.2 10.97(2) 10.52 9.99(2) 11.71(1) 11.22(1) 9.84 8.9(2) 8.13 9.92(10) 9.96(10) 9.72(2) 12.6 8.65 8.69 10.82(3) 10.78(2) 9.9 8.83(2) 8.83(2) 8.69(2) 9.81(3) 12.39 7.59(2) 7.29 8.29 8.14 8.13 10.08 9.9

⌬f H (ion) in kJ · mol⫺1 1803 2000 935 1242 929 936 1089 1368 617 962 815 597 815 1276 835 883 844 929 1030 626 628 693 946 756 985 870 1001 1247 1244 906 995 999 126 99 680 692 912 895 950 869 869 855 373 485 1016 1026 668 660 659 625 604

short standard long

DEAN #37261

(McGHP)

RIGHT

PROPERTIES OF ATOMS, RADICALS, AND BONDS

INTERACTIVE

4.11

top of rh base of rh cap height base of text

TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species Cumene Cyanamide Cyanate (NCO) Cyanide (CN) Cyanoacetylene Cyanogen Cyanogen chloride Cyanogen fluoride Cyclobutane Cyclobutanone Cyclobutene Cycloheptane Cyclohexane Cyclohexanol Cyclohexanone Cyclohexene Cyclohexylamine Cyclohexylcyclohexane Cyclooctane Cyclopropane Cyclopropanecarbonitrile Cyclopropanone Cyclopropene Cyclopropylamine Cyclopropylbenzene cis-Decahydronaphthalene trans-Decahydronaphthalene Decane 1-Decene Diazomethane 1,4-Dibromobutane 1,2-Dibromoethane Dibromofluoromethane Dibromomethane 1,2-Dibromopropane 1,3-Dibromopropane 1,2-Dibromotetrafluoroethane Dibutyl ether Di-sec-butyl ether Di-tert-butyl ether Dibutyl sulfide Di-tert-butyl sulfide Dibutylamine Dichloroacetyl chloride Dichloroacetylene m-Dichlorobenzene o-Dichlorobenzene p-Dichlorobenzene Dichlorodifluoromethane Dichlorodimethylsilane 1,1-Dichloroethane

In MJ · mol⫺1

In electron volts

0.842 1.00 1.135(1) 1.360 1.123(1) 1.290(1) 1.191(1) 1.285(1) 0.957(5) 0.9025 0.910 0.962 0.951(3) 0.941 0.882(1) 0.8631(10) 0.832(23) 0.908 0.942 0.951 0.989 0.88(1) 0.930 0.84 0.806 0.893 0.892 0.931 0.909(1) 0.8683(1) 0.979 1.001 1.069(3) 1.013(2) 0.975 0.990 1.07 0.910 0.879 0.850 0.79 0.77 0.742(3) 1.06 0.974 0.879(1) 0.876(1) 0.856(1) 1.134(4) 1.03 1.067

8.73(1) 10.4 11.76(1) 14.09 11.64(1) 13.37(1) 12.34(1) 13.32(1) 9.92(5) 9.354 9.43 9.97 9.86(3) 9.75 9.14(1) 8.945(10) 8.62(24) 9.41 9.76 9.86 10.25 9.1(1) 9.67(1) 8.7 8.35 9.26 9.24 9.65 9.42(1) 8.999(1) 10.15 10.37 11.07(3) 10.50(2) 10.1 10.26 11.1 9.43 9.11 8.81 8.2 8.0 7.69(3) 11.0 10.09 9.11(1) 9.08(1) 8.89(1) 11.75(4) 10.7 11.06

⌬f H (ion) in kJ · mol⫺1 847 1137 1290 1795 1475 1597 1329 1323 986 815 1067 844 828 651 656 859 727 690 817 1005 1173 895 1209 916 956 724 710 682 786 1098 879 963 687 1013 903 919 280 575 511 486 624 583 586 819 1183 907 909 882 656 576 937

short standard long

DEAN #37261

LEFT

(McGHP)

4.12

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species 1,2-Dichloroethane 1,1-Dichloroethylene cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene Dichlorofluoromethane Dichloromethane Dichloromethylene 1,2-Dichloropropane 1,3-Dichloropropane 1,2-Dichlorotetrafluoroethane Dicyclopropyl ketone 1,1-Diethoxyethane Diethyl oxalate m-Diethylbenzene o-Diethylbenzene p-Diethylbenzene Diethylene glycol dimethyl ether m-Difluorobenzene o-Difluorobenzene p-Difluorobenzene 1,1-Difluoroethane 1,1-Difluoroethylene cis-1,2-Difluoroethylene Difluoromethane Difluoromethylene 2,5-Dihydrothiophene Diiodomethane Diisobutyl sulfide Diisobutylamine Diisopropyl ether Diisopropyl sulfide Diisopropylamine Diketene Dimethoxymethane Dimethyl disulfide Dimethyl ether Dimethyl oxalate o-Dimethyl phthalate Dimethyl sulfide Dimethyl sulfoxide Dimethylamine N,N-Dimethylaniline 2,2-Dimethylbutane 2,3-Dimethylbutane 3,3-Dimethyl-2-butanone 2,3-Dimethyl-1-butene 2,3-Dimethyl-2-butene 3,3-Dimethyl-1-butyne 1,1-Dimethylcyclohexane cis-1,2-Dimethylcyclohexane cis-1,3-Dimethylcyclohexane

In MJ · mol⫺1

In electron volts

1.065 0.945(4) 0.932(1) 0.931(2) 1.11 1.092(1) 1.000 1.049(5) 1.047(5) 1.18 0.88 0.944 0.95 0.819(1) 0.821 0.810 0.96 0.900(1) 0.895(1) 0.882(1) 1.145(3) 0.993(1) 0.987 1.226 1.102(1) 0.81 0.913(2) 0.807(5) 0.754 0.888(5) 0.833(5) 0.746(3) 0.93(2) 0.92 0.71 0.9673(23) 0.965 0.930(7) 0.838(1) 0.878 0.794(8) 0.687(2) 0.971 0.967 0.879(2) 0.875(1) 0.798(1) 0.946(5) 0.909 ⬍0.944 ⬍0.963

11.04 9.79(4) 9.66(1) 9.65(2) 11.5 11.32(1) 10.36 10.87(5) 10.85(5) 12.2 9.1 9.78 9.8 8.49(1) 8.51 8.40 9.8 9.33(1) 9.28(1) 9.14(1) 11.87(3) 10.29(1) 10.23 12.71 11.42(1) 8.4 9.46(2) 8.36(5) 7.81 9.20(5) 8.63(5) 7.73(3) 9.6(2) 9.5 7.4(3) 10.025(25) 10.0 9.64(7) 8.69(1) 9.01 8.23(8) 7.12(2) 10.06 10.02 9.11(2) 9.07(1) 8.27(1) 9.80(5) 9.42 ⬍9.78 ⬍9.98

⌬f H (ion) in kJ · mol⫺1 931 947 936 935 829 996 1163 886 888 252 1041 490 205 798 804 790 448 591 602 575 643 650 690 774 897 898 1030 627 574 569 630 602 736 569 690 783 287 277 801 718 776 787 787 791 589 812 729 1050 728 772 778

short standard long

DEAN #37261

(McGHP)

RIGHT

PROPERTIES OF ATOMS, RADICALS, AND BONDS

INTERACTIVE

4.13

top of rh base of rh cap height base of text

TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species cis-1,4-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane trans-1,3-Dimethylcyclohexane trans-1,4-Dimethylcyclohexane cis-1,2-Dimethylcyclopentane trans-1,2-Dimethylcyclopentane N,N-Dimethylformamide 2,6-Dimethyl-4-heptanone 1,1-Dimethylhydrazine 2,4-Dimethyl-3-pentanone 2,3-Dimethylpyridine 2,4-Dimethylpyridine 2,5-Dimethylpyridine 2,6-Dimethylpyridine 3,4-Dimethylpyridine 3,5-Dimethylpyridine N,N-Dimethyl-o-toluidine 1,3-Dioxane 1,4-Dioxane 1,3-Dioxolane Diphenyl ether Diphenylacetylene Diphenylamine 1,2-Diphenylethane Diphenylmethane Dipropyl ether Dipropyl sulfide Dipropylamine Divinyl ether 5,7-Dodecadiyne Dodecafluorocyclohexane Epichlorohydrin 1,2-Epoxybutane Ethane 1,2-Ethanediamine Ethanethiol Ethanol Ethanolamine Ethyl benzoate Ethyl formate Ethyl methyl ether Ethyl methyl sulfide Ethyl pentyl ether Ethyl vinyl ether Ethylamine N-Ethylaniline Ethylbenzene 2-Ethyl-1-butene Ethylcyclohexane Ethylcyclopentane Ethylene

In MJ · mol⫺1 ⬍0.958 0.908 0.920 0.922 0.957(5) 0.960(5) 0.881(2) 0.872(3) 0.702(4) 0.864(1) 0.854(2) 0.854(3) 0.849(5) 0.847(3) 0.883 0.893 0.714(2) 0.95 0.887(1) 0.96 0.781(3) 0.762(2) 0.691(4) 0.84(1) 0.825(3) 0.894(5) 0.801(2) 0.746(3) 0.84 0.837 1.27 0.98 0.98 1.112(1) 0.83 0.8959(5) 1.010(2) 0.865 0.86 1.024(1) 0.938 0.824(10) 9.16 0.85 0.855(2) 0.740 0.846(1) 0.874(2) 0.920 0.976(2) 1.0382(4)

In electron volts

⌬f H (ion) in kJ · mol⫺1

⬍9.93 9.41 9.53 9.56 9.92(5) 9.95(5) 9.13(2) 9.04(3) 7.28(4) 8.95(1) 8.85(2) 8.85(3) 8.80(5) 8.86(3) 9.15 9.25 7.40(2) 9.8 9.19(1) 9.9 8.09(3) 7.90(2) 7.16(4) 8.7(1) 8.55(3) 9.27(5) 8.30(2) 7.73(3) 8.7 8.67 13.2 10.2 10.15 11.52(1) 8.6 9.285(5) 10.47(2) 8.96 8.9 10.61(1) 9.72 8.54(10) 9.49 8.8 8.86(2) 7.67 8.77(1) 9.06(2) 9.54 10.12(2) 10.507(4)

782 728 743 738 828 823 689 515 786 552 922 918 916 913 953 965 814 607 571 658 766 1164 908 983 963 602 676 641 827 1079 ⫺1095 875 862 1027 812 849 776 664 537 639 722 765 602 707 808 794 876 818 748 850 1066

short standard long

DEAN #37261

LEFT

(McGHP)

4.14

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species Ethylene glycol Ethylene oxide Ethyleneimine p-Ethylphenol Ethynyl (HC # C) Fluoranthene Fluorene Fluoroacetylene Fluorobenzene Fluoroethane Fluoroethylene Fluoromethane Fluoromethylene Fluoromethylidene (CF) p-Fluoronitrobenzene 1-Fluoropropane 2-Fluoropropane 3-Fluoropropene m-Fluorotoluene o-Fluorotoluene p-Fluorotoluene Formaldehyde Formamide Formic acid Fulminic acid (HCNO) Fulvene Fumaric acid Furan Glyoxal 1-Heptanal Heptane 1-Heptanol 2-Heptanol 3-Heptanol 4-Heptanol 2-Heptanone 1-Heptene 2-Heptene 3-Heptene Hexachlorobenzene Hexachloroethane 1,5-Hexadiene Hexafluoroacetone Hexafluorobenzene Hexafluoroethane Hexafluoropropene Hexamethylbenzene 1-Hexanal Hexane Hexanoic acid 1-Hexanol

In MJ · mol⫺1

In electron volts

⌬f H (ion) in kJ · mol⫺1

0.980 1.0195(10) 0.89(1) 0.756 1.13 0.768(4) 0.761(3) 1.086 0.8877(5) 1.12 1.0000(15) 1.203(2) 1.012 0.879(1) 0.955 1.09 1.069(2) 0.975 0.860(1) 0.860(1) 0.848(1) 1.0492(2) 0.980(6) 1.093(1) 1.045 0.807 1.03 0.8571(3) 0.975 0.931(2) 0.957(5) 0.949(3) 0.936(3) 0.934(3) 0.927(3) 0.897(1) 0.911 0.853(2) 0.861 0.866 1.07 0.896(5) 1.104 0.9558 1.29 1.023(3) 0.757 0.933(5) 0.977 0.976 0.954(3)

10.16 10.566(10) 9.2(1) 7.84 11.7 7.95(4) 7.89(3) 11.26 9.200(5) 11.6 10.363(15) 12.47(2) 10.49 9.11(1) 9.90 11.3 11.08(2) 10.11 8.91(1) 8.91(1) 8.79(1) 10.874(2) 10.16(6) 11.33(1) 10.83 8.36 10.7 8.883(3) 10.1 9.65(2) 9.92(5) 9.84(3) 9.70(3) 9.68(3) 9.61(3) 9.30(1) 9.44 8.84(2) 8.92 8.98 11.1 9.29(5) 11.44 9.906 13.4 10.60(3) 7.85 9.67(5) 10.13 10.12 9.89(3)

593 967 1014 613 1694 1057 950 1195 772 856 861 956 1121 1134 826 806 776 821 709 709 701 940 796 715 1263 1031 355 822 763 668 770 614 580 578 572 596 849 782 790 822 920 980 ⫺294 10 ⫺50 ⫺103 670 686 810 463 639

short standard long

DEAN #37261

(McGHP)

RIGHT

PROPERTIES OF ATOMS, RADICALS, AND BONDS

INTERACTIVE

4.15

top of rh base of rh cap height base of text

TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species 2-Hexanol 3-Hexanol 2-Hexanone 3-Hexanone 1-Hexene cis-2-Hexene trans-2-Hexene Hexylamine 1-Hexyne Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) p-Hydroquinone Imidazole Indane Indene Iodobenzene Iodoethane 1-Iodohexane Iodomethane 1-Iodopropane 2-Iodopropane Isobutylbenzene Isocyanic acid Isophthalic acid Isopropylcyclohexane Isoquinoline Isoxazole Ketene Maleic anhydride Mesityl oxide Methacrylic acid Methane Methanethiol Methanol Methoxy Methoxybenzene (Anisole) 2-Methoxyethanol Methyl Methyl acetate Methyl acrylate Methyl azide Methyl benzoate Methyl chloroacetate Methyl 2,2-dimethylpropanoate Methyl formate Methyl pentanoate Methyl pentyl ether Methyl vinyl ether Methylacrylonitrile Methylamine 2-Methylaniline

In MJ · mol⫺1

In electron volts

0.946(3) 0.929(3) 0.902(2) 0.880(2) 0.911(4) 0.865(1) 0.865(1) 0.833(5) 0.960 1.312(1) 1.21(1) 0.767(3) 0.850(1) 0.90 0.785(1) 0.8380 0.9018 0.8857 0.9203 0.8943 0.8853 0.838(1) 1.120(3) 0.963(20) 0.900 0.8239(3) 0.958(5) 0.927(2) 1.04 0.876(3) 0.979 1.207 9.108(5) 1.047(1) 0.83 0.792(2) 0.93 0.949(1) 0.991(2) 0.96 0.947(2) 0.899(3) 0.99 0.955(4) 1.0435(5) 1.00(2) 0.933 0.862(2) 0.998 0.865(2) 0.718(2)

9.80(3) 9.63(3) 9.35(2) 9.12(2) 9.44(4) 8.97(1) 8.97(1) 8.63(5) 9.95(5) 13.60(1) 12.5(1) 7.95(3) 8.81(1) 9.3 8.14(1) 8.685 9.346 9.179 9.538 9.269 9.175 8.68(1) 11.61(3) 9.98(20) 9.33 8.539(3) 9.93(5) 9.61(2) 10.8 9.08(3) 10.15 12.51 9.440(5) 10.85(1) 8.6 8.21(2) 9.6 9.84(1) 10.27(2) 9.9 9.81(2) 9.32(3) 10.3 9.90(4) 10.815(5) 10.4(2) 9.67 8.93(2) 10.34 8.97(2) 7.44(2)

⌬f H (ion) in kJ · mol⫺1 611 599 626 600 869 818 814 699 1081 1447 1407 504 997 864 949 1003 893 794 936 862 844 816 1016 268 704 1032 1038 880 645 692 611 1133 888 845 845 724 562 1095 581 611 1227 611 575 466 688 532 657 761 1127 843 772

short standard long

DEAN #37261

LEFT

(McGHP)

4.16

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species

In MJ · mol⫺1

In electron volts

3-Methylaniline 4-Methylaniline N-Methylaniline Methylcyclohexane 1-Methylcyclohexanol Methylcyclopentane Methylcyclopropane 2-Methyldecane Methylene N-Methylformamide 2-Methylheptane 5-Methyl-2-hexanone Methylhydrazine Methylidyne Methylisocyanate 1-Methyl-4-isopropylbenzene (p-Cymene) 1-Methylnaphthalene 2-Methylnaphthalene Methyloxirane 2-Methylpentane 3-Methylpentane 2-Methyl-3-pentanone 3-Methyl-2-pentanone 4-Methyl-2-pentanone 2-Methyl-1-pentene 2-Methyl-2-pentene 4-Methyl-1-pentene 4-Methyl-cis-2-pentene 4-Methyl-trans-2-pentene 2-Methylpropanal 2-Methylpropanenitrile 2-Methylpropenal 2-Methylpropene (Isobutene) 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine Methylsilane m-Methylstyrene o-Methylstyrene p-Methylstyrene Methyltrichlorosilane Naphthalene 1-Naphthol 2-Naphthol Nickel carbonyl m-Nitroaniline o-Nitroaniline p-Nitroaniline Nitrobenzene Nitroethane

0.724(2) 0.698(2) 0.707(2) 0.930 0.95(2) 0.950(3) 0.913 0.934 1.0031(3) 0.945 0.949 0.895(1) 0.740(2) 1.027(1) 1.030(2) 0.800 0.757 0.75 0.986(2) 0.976 0.973 0.878(1) 0.889(1) 0.897(1) 0.876(1) 0.828 0.912(1) 0.866(1) 0.865(1) 0.9364(5) 1.09 0.951 0.8915(3) 0.870(3) 0.872(3) 0.872(3) 1.03 0.786(2) 0.888(2) 0.78(1) 1.096(3) 0.785(1) 0.749(3) 0.757(5) 0.798(4) 0.802(2) 0.798(1) 0.804(1) 0.951(2) 1.050(5)

7.50(2) 7.24(2) 7.33(2) 9.64 9.8(2) 9.85(3) 9.46 9.68 10.396(3) 9.79 9.84 9.28(1) 7.67(2) 10.64(1) 10.67(2) 8.29 7.85 7.8 10.22(2) 10.12 10.08 9.10(1) 9.21(1) 9.30(1) 9.08(1) 8.58 9.45(1) 8.98(1) 8.97(1) 9.705(5) 11.3 9.86 9.239(3) 9.02(3) 9.04(3) 9.04(3) 10.7 8.15(2) 9.20(2) 8.1(1) 11.36(3) 8.14(1) 7.76(3) 7.85(5) 8.27(4) 8.31(2) 8.27(1) 8.34(1) 9.86(2) 10.88(5)

⌬f H (ion) in kJ · mol⫺1 778 753 791 775 586 845 936 685 1386 756 734 586 835 1622 900 771 870 866 892 802 801 592 600 609 817 761 862 809 804 721 1115 834 875 970 979 976 1003 908 908 895 548 936 719 727 200 865 861 850 1019 948

short standard long

DEAN #37261

(McGHP)

RIGHT

PROPERTIES OF ATOMS, RADICALS, AND BONDS

INTERACTIVE

4.17

top of rh base of rh cap height base of text

TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species Nitromethane m-Nitrophenol o-Nitrophenol p-Nitrophenol 1-Nitropropane 2-Nitropropane m-Nitrotoluene o-Nitrotoluene p-Nitrotoluene Nonane 2-Nonanone 5-Nonanone Octafluoronaphthalene Octafluoropropane Octafluorotoluene Octane 1-Octene 1-Octyne 2-Octyne 3-Octyne 4-Octyne Oxazole Oxetane 2-Oxetanone Oxomethyl (HCO) Pentafluorobenzene Pentafluorophenol 2,3,4,5,6-Pentafluorotoluene Pentanchloroethane Pentylamine Perylene Phenanthrene Phenetole Phenol Phenylacetic acid m-Phenylenediamine o-Phenylenediamine p-Phenylenediamine Phthalic anhydride ␣-Pinene Propanal Propanamide Propane Propanenitrile 1-Propanethiol 2-Propanethiol Propanoic acid 1-Propanol 2-Propanol

In MJ · mol⫺1

In electron volts

⌬f H (ion) in kJ · mol⫺1

1.063(4) 0.86 0.88 0.88 1.043(3) 1.033(5) 0.15(2) 0.912(4) 0.91 0.938 0.884 0.875 0.854 1.291 0.96 0.948 0.910(1) 0.960(2) 0.898(1) 0.890(1) 0.888(1) 0.93 0.9328(5) 0.936(1) 0.782(5) 0.929 0.888(2) 0.91 1.06 0.837 0.666(1) 0.758(2) 0.784(2) 0.817 0.797 0.689 0.69 0.663(5) 0.96 0.779 0.9603(5) 0.92 1.057(5) 1.142(2) 0.8872(5) 0.882 1.0155(3) 0.986(3) 0.976(8)

11.02(4) 9.0 9.1 9.1 10.81(3) 10.71(5) 9.48(2) 9.45(4) 9.4 9.72 9.16 9.07 8.85 13.38 9.9 9.82 9.43(1) 9.95(2) 9.31(1) 9.22(1) 9.20(1) 9.6 9.668(5) 9.70(1) 8.10(5) 9.63 9.20(2) 9.4 11.0 8.67 6.90(1) 7.86(2) 8.13(2) 8.47 8.26 7.14 7.2 6.87(5) 10.0 8.07 9.953(5) 9.5 10.95(5) 11.84(2) 9.195(5) 9.14 10.525(3) 10.22(3) 10.12(8)

988 755 782 761 919 894 944 966 936 710 545 530 ⫺368 ⫺491 ⫺233 739 829 1040 961 952 946 910 853 653 826 122 ⫺71 64 919 728 975 963 683 721 479 777 787 759 593 808 773 720 952 1194 819 806 568 731 704

short standard long

DEAN #37261

LEFT

(McGHP)

4.18

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species Propenal Propene Propenenitrile Propenoic acid 1-Propylamine 2-Propylamine Propylbenzene Propylcyclohexane Propylcyclopentane Propyleneimine Propynal Propyne 2-Propyn-1-ol Pyrene Pyridazine Pyrimidine Pyrrole 2-Pyrrolidone Quinoline cis-Stilbene trans-Stilbene Styrene Succinic anhydride Succinonitrile Terephthalic acid m-Terphenyl o-Terphenyl p-Terphenyl Tetrabromomethane Tetrachloro-1,2-difluoroethane 1,1,1,2-Tetrachloroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetrachloromethane Tetraethylsilane 1,2,3,4-Tetrafluorobenzene 1,2,3,5-Tetrafluorobenzene 1,2,4,5-Tetrafluorobenzene Tetrafluoroethylene Tetrahydrofurane 1,2,3,4-Tetrahydronaphthalene 1,2,4,5-Tetramethylbenzene 2,2,3,3-Tetramethylbutane Thiacyclobutane Thiophene p-Tolualdehyde Toluene m-Toluic acid o-Toluic acid p-Toluic acid

In MJ · mol⫺1

In electron volts

0.975(6) 0.939(2) 1.053(1) 1.023 0.847(2) 0.841(3) 0.841(1) 0.913 0.965(4) 0.87 1.04 1.000(1) 1.014 0.715 0.834 0.891 0.7920(5) 0.89 0.832(1) 0.753(2) 0.743(3) 0.813(6) 1.02 1.158(24) 0.951(20) 0.773(1) 0.77 0.751(1) 0.995(2) 1.09 1.07 1.121 0.899 1.107(1) 0.86 0.920(1) 0.920(1) 0.902(1) 0.976(2) 0.908(2) 0.817 0.776(1) 0.95 0.838 0.856(4) 0.900(5) 0.851(1) 0.910(20) 0.88 0.891(20)

10.103(6) 9.73(2) 10.91(1) 10.60 8.78(2) 8.72(3) 8.72(1) 9.46 10.00(4) 9.0 10.8 10.36(1) 10.51 7.41 8.64 9.23 8.208(5) 9.2 8.62(1) 7.80(2) 7.70(3) 8.43(6) 10.6 12.10(25) 9.86(20) 8.01(1) 8.0 7.78(1) 10.31(2) 11.3 11.1 11.62 9.32 11.47(1) 8.9 9.53(1) 9.53(1) 9.35(1) 10.12(2) 9.41(2) 8.47 8.04(1) 9.8 8.69 8.87(4) 9.33(5) 8.82(1) 9.43(20) 9.1 9.23(20)

⌬f H (ion) in kJ · mol⫺1 900 959 1237 701 777 758 849 720 817 960 1155 1186 1060 933 1112 1087 900 674 1041 1005 977 961 500 1377 232 1057 1056 1035 1079 563 920 971 887 1011 595 284 263 254 315 724 842 730 720 899 971 825 901 579 558 560

short standard long

DEAN #37261

(McGHP)

RIGHT

PROPERTIES OF ATOMS, RADICALS, AND BONDS

INTERACTIVE

4.19

top of rh base of rh cap height base of text

TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species m-Tolunitrile o-Tolunitrile p-Tolunitrile Tribromomethane Tributylamine Trichloroacetyl chloride 1,2,4-Trichlorobenzene 1,3,5-Trichlorobenzene 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane Trichloromethane Trichloromethylbenzene 1,1,2-Trichlorotrifluoroethane Triethanolamine Triethylamine Trifluoroacetic acid Trifluoroacetonitrile 1,1,1-Trifluoro-2-bromo-2-chloroethane 1,1,1-Trifluoroethane Trifluoroethylene Trifluoroiodomethane Trifluoromethane Trifluoromethyl (CF3) Trifluoromethylbenzene 3,3,3-Trifluoropropene Triiodomethane Trimethylamine 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Trimethylborate Trimethylchlorosilane 3,5,5-Trimethylcyclohex-2-en-1-one 2,2,4-Trimethylpentane 2,2,4-Trimethyl-3-pentanone 2,4,6-Trimethylpyridine Trioxane Undecane Urea Vinyl acetate m-Xylene o-Xylene p-Xylene 2,3-Xylenol 2,4-Xylenol 2,6-Xylenol 3,4-Xylenol

In MJ · mol⫺1

In electron volts

0.901 0.905 0.899 1.011(2) 0.71 1.06 0.872 0.899(2) 1.06 1.06 0.914(1) 1.136(2) 1.097(2) 0.926 1.157(2) 0.76 0.724 1.106 1.337 1.06 1.24(1) 0.978 0.987 1.337 0.86 0.9345(4) 1.05 0.893(2) 0.755462 0.812(2) 0.798(1) 0.811(1) 0.96 0.979 0.875 0.951 0.849(1) 0.88(1) 0.99 0.922 0.94 0.887 0.826(1) 0.826(1) 0.814(1) 0.797 0.77 0.777(2) 0.781

9.34 9.38 9.32 10.48(2) 7.4 11.0 9.04 9.32(2) 11.0 11.0 9.47(1) 11.77(2) 11.37(2) 9.60 11.99(2) 7.9 7.50 11.46 13.86 11.0 12.9(1) 10.14 10.23 13.86 8.9 9.685(4) 10.9 9.25(2) 7.82960 8.42(2) 8.27(1) 8.41(1) 10.0 10.15 9.07 9.86 8.80(1) 8.9(1) 10.3 9.56 9.7 9.19 8.56(1) 8.56(1) 8.44(1) 8.26 8.0 8.05(2) 8.09

⌬f H (ion) in kJ · mol⫺1 1085 1085 1083 1035 492 827 880 899 917 911 895 868 992 914 429 206 631 75 838 362 496 489 397 643 399 335 437 1010 731 803 784 796 65 624 670 713 511 580 528 650 690 572 843 844 832 640 609 615 624

short standard long

DEAN #37261

LEFT

(McGHP)

4.20

INTERACTIVE

top of rh base of rh

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TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Inorganic compounds Ionization energy Species Aluminum tribromide Aluminum trichloride Aluminum trifluoride Aluminum triiodide Amidogen (NH2) Ammonia Antimony trichloride Arsenic trichloride Arsenic trifluoride Arsine Barium oxide Bismuth trichloride Borane (BH3) Boron dioxide (BO2) Boron oxide (B2O3) Boron tribromide Boron trichloride Boron trifluoride Boron triodide Bromine (Br2) Bromine chloride (BrCl) Bromine fluoride (BrF) Bromine pentafluoride Bromosilane (BrSiH3) Calcium oxide Cesium chloride Cesium fluoride Cesium fluoride Chlorine (Cl2) Chlorine difluoride Chlorine dioxide Chlorine oxide Chlorine trifluoride Chlorosilane (ClSiH3) Chromyl chloride (CrO2Cl2) Diborane (B2H6) Dichlorosilane (Cl2SiH2) Difluoramine (HNF2) Difluoroamidogen (NF2) Difluorosilane (F2SiH2) Dioxygen fluoride Disilane Disulfur oxide Fluorine (F2) Fluorosilane (FSiH3) Gallium bromide Gallium chloride Gallium triiodide Gallium(I) fluoride

In MJ · mol⫺1 1.00 1.159 1.394 0.88 1.075(1) 0.980(1) 0.97(1) 1.018(3) 1.239(5) 0.954 0.667(6) 1.00 1.19(1) 1.30(3) 1.303(14) 1.014(2) 1.119(2) 1.501(3) 0.893(3) 1.0146(5) 1.062 1.136(1) 1.271(1) 1.02 0.67 0.756(5) 1.221(1) 0.849(10) 1.1424(5) 1.232(5) 1.000(2) 1.057 1.221(5) 1.10 1.12 1.098(3) 1.10 1.112(8) 1.122(1) 1.18 1.22(2) 0.94 1.017(4) 1.5146(3) 1.13 1.003 1.112 0.907 0.93(5)

In electron volts

⌬f H (ion) in kJ · mol⫺1

10.4 12.01 14.45 9.1 11.14(1) 10.16(1) 10.1(1) 10.55(3) 12.84(5) 9.89 6.91(6) 10.4 12.3(1) 13.5(3) 13.50(15) 10.51(2) 11.60(2) 15.56(3) 9.25(3) 10.515(5) 11.01 11.77(1) 13.17(1) 10.6 6.9 7.84(5) 12.65(1) 8.80(10) 11.840(5) 12.77(5) 10.36(2) 10.95 12.65(5) 11.4 11.6 11.38(3) 11.4 11.53(8) 11.628(1) 12.2 12.6(2) 9.7 10.54(4) 15.697(3) 11.7 10.40 11.52 9.40 9.6(5)

593 573 282 673 1264 934 661 754 452 1021 543 736 1287 1001 460 809 718 365 964 1046 1079 1077 840 943 691 510 1170 489 1108 1128 1096 1159 1057 899 580 1134 765 1046 1155 386 1228 1015 967 1515 752 711 648 765 700

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TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species Germane (GeH4) Germanium oxide (GeO) Germanium sulfide (GeS) Germanium tetrachloride Germanium tetrafluoride Germanium tetraiodide Hafnium bromide Hafnium chloride Hexaborane (B6H10) Hydrazine Hydrazoic acid (HN3) Hydrogen (H2) Hydrogen bromide Hydrogen chloride Hydrogen fluoride Hydrogen iodide Hydrogen peroxide Hydrogen selenide Hydrogen sulfide Hydroperoxy (HOO) Hydroxyl (OH) Hydroxylamine (NH2OH) Hypochlorous acid (HOCl) Hypofluorous acid (HOF) Imidogen (NH) Iodine (I2) Iodine bromide Iodine chloride Iodine fluoride Iodine pentafluoride Lead oxide (PbO) Lead(II) chloride Lead(II) fluoride Lead(II) sulfide Lithium bromide Lithium chloride Lithium hydride Lithium iodide Lithium oxide Magnesium fluoride Magnesium oxide Mercapto (SH) Mercury(II) bromide Mercury(II) chloride Mercury(II) iodide Molybdenum hexafluoride Molybdenum(V) chloride Niobium(V) chloride Nitric acid

In MJ · mol⫺1 1.093 1.085(1) 0.963(2) 1.1270(5) 1.50 0.909 1.05 1.13 0.87 7.82(14) 1.0344(24) 1.488413(5) 1.125(3) 1.2299 1.5481(3) 1.0004(1) 1.017 0.9535(1) 1.0085(8) 1.095(1) 1.254 0.947 1.073(1) 1.226(1) 1.302(1) 0.90694(12) 0.9446(4) 0.9734(10) 1.025 1.2488(5) 0.976(10) 0.96 1.11 0.825 0.84 0.923 0.74 0.72 0.815 1.29 0.93 1.001 1.019(3) 1.0988(3) 0.91748(22) 1.40(1) 0.84 1.058 1.153(1)

In electron volts

⌬f H (ion) in kJ · mol⫺1

11.33 11.25(1) 9.98(2) 11.68(5) 15.5 9.42 10.9 11.7 9.0 8.10(15) 10.720(25) 15.42589(5) 11.66(3) 12.747 16.044(3) 10.368(1) 10.54 9.882(1) 10.453(8) 11.35(1) 13.00 10.00 11.12(1) 12.71(1) 13.49(1) 9.3995(12) 9.790(4) 10.088(10) 10.62 12.943(5) 9.08(10) 10.0 11.5 8.5(5) 8.7 9.57 7.7 7.5 8.45(20) 13.4 9.7 10.37 10.560(3) 11.380(3) 9.5088(22) 14.5(1) 8.7 10.97 11.95(1)

1185 1044 1055 629 307 850 366 246 965 877 1328 1488 1087 1137 1276 1028 881 983 988 1106 1293 923 993 1130 1678 969 986 991 930 408 939 789 679 954 685 727 882 633 895 569 992 1140 935 952 900 ⫺159 392 656 1019

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TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species Nitric oxide Nitrogen (N2) Nitrogen dioxide Nitrogen pentoxide Nitrogen tetroxide Nitrogen trichloride Nitrogen trifluoride Nitrosyl bromide Nitrosyl chloride (NOCl) Nitrosyl fluoride (NOF) Nitrous acid (HONO) Nitrous oxide (N2O) Nitryl chloride (NO2Cl) Nitryl fluoride (NO2F) Osmium tetroxide Oxygen (O2) Oxygen dichloride Oxygen difluoride (OF2) Oxygen fluoride Ozone (O3) Pentaborane (B5H9) Perchloryl fluoride (ClO3F) Phosphine (PH3) Phosphorus (P2) Phosphorus nitride Phosphorus pentachloride Phosphorus pentafluoride Phosphorus sulfur trichloride (PSCl3) Phosphorus tribromide Phosphorus trichloride Phosphorus trifluoride Phosphoryl chloride (POCl3) Phosphoryl trifluoride (POF3) Potassium bromide Potassium chloride Potassium iodide Rhenium(VII) oxide Rubidium bromide Rubidium chloride Ruthenium tetroxide Silane Silicon oxide (SiO) Silicon tetrachloride Silicon tetrafluoride Silver chloride Silver fluoride Sodium bromide Sodium chloride Sodium iodide Stibine (SbH3)

In MJ · mol⫺1 0.893900(6) 1.59336 0.941(1) 1.15 1.04(2) 0.9765(10) 1.254(2) 0.981(3) 1.049(1) 1.219(3) 1.09 1.2433 1.142 1.263 1.1895 1.1647(1) 1.056 1.265(1) 1.232 1.199 0.955(4) 1.2490(5) 0.9522(2) 1.016 1.143 1.03 1.46 0.956 0.94 0.956 1.104 1.096(2) 1.231(1) 0.757(10) 0.77(4) 0.696(29) 1.23(2) 0.766(3) 0.820(3) 1.172(3) 1.124 1.103 1.136(1) 1.51 0.973 1.06(3) 0.802(10) 0.861(6) 0.737(2) 0.920(3)

In electron volts

⌬f H (ion) in kJ · mol⫺1

9.26436(6) 15.5808 9.75(1) 11.9 10.8(2) 10.12(10) 13.00(2) 10.17(3) 10.87(1) 12.63(3) 11.3 12.886 11.84 13.09 12.320 12.071(1) 10.94 13.11(1) 12.77 12.43 9.90(4) 12.945(5) 9.869(2) 10.53 11.85 10.7 15.1 9.91 9.7 9.91 11.44 11.36(2) 12.76(1) 7.85(10) 8.0(4) 7.21(30) 12.7(2) 7.94(3) 8.50(3) 12.15(3) 11.65 11.43 11.79(1) 15.7 10.08 11.0(3) 8.31(10) 8.92(6) 7.64(2) 9.54(3)

985 1503 974 1161 1050 1244 1125 1065 1099 1152 977 1325 1155 1154 850 1165 1135 1290 1341 1342 1028 1224 958 1160 1248 656 ⫺137 668 798 668 146 540 ⫺24 578 557 570 125 583 590 988 1158 1002 527 ⫺100 1065 1071 660 681 659 1067

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TABLE 4.3 Ionization Energy of Molecular and Radical Species (Continued) Ionization energy Species Strontium oxide Sulfur (S2) Sulfur chloride pentafluoride Sulfur dichloride Sulfur difluoride Sulfur dioxide Sulfur hexafluoride Sulfur oxide (SO) Sulfur pentafluoride Sulfur trioxide Sulfuryl chloride (SO2Cl2) Sulfuryl fluoride (SO2F2) Tantalum(V) chloride Tetraborane (B4H10) Tetrafluorohydrazine (gauche) Thallium(I) bromide Thallium(I) chloride Thallium(I) fluoride Thionitrosyl fluoride (NSF) Thionyl chloride Thionyl fluoride Thiophosphoryl trifluoride (PSF3) Thorium(IV) oxide Tin(II) bromide Tin(II) chloride Tin(II) fluoride Tin(II) oxide Tin(II) sulfide Tin(IV) bromide Tin(IV) chloride Tin(IV) hydride Titanium(IV) bromide Titanium(IV) chloride Titanium(IV) oxide trans-Difluorodiazine Trifluoramine oxide (NOF3) Trifluorosilane (F3SiH) Trisilane Tungsten(VI) chloride Uranium hexafluoride Uranium(IV) oxide Uranium(VI) oxide Vanadium(IV) chloride Vanadium(V) oxychloride (VOCl3) Water Xenon difluoride Xenon tetrafluoride Zirconium bromide Zirconium chloride

In MJ · mol⫺1

In electron volts

⌬f H (ion) in kJ · mol⫺1

7.00(15) 9.356(2) 12.335(5) 9.45(3) 10.08 12.32(2) 15.33(3) 10.32(2) 10.5(1) 12.80(4) 12.05 11.5 11.08 10.76(4) 11.94(3) 9.14(2) 9.70(3) 10.52 11.51(4) 10.96 12.25 11.05(4) 8.70(15) 9.0 10.0 11.1 9.60(2) 8.8 10.6 11.88(5) 10.75 10.3 11.65(15) 9.54(10) 12.8 13.26(1) 14.0 9.2 9.5 14.00(10) 5.4(1) 10.5(5) 9.2 11.61 12.612(10) 12.35(1) 12.65(10) 10.7 11.2

662 1031 144 895 676 892 259 1001 97 839 807 679 348 1105 1119 844 869 835 1090 844 688 58 342 830 760 586 944 966 709 673 1200 375 363 623 1315 1116 150 1009 348 ⫺796 57 214 210 425 975 1083 1016 388 392

0.675(14) 0.9027(2) 1.1921(5) 0.912(3) 0.973 1.189(2) 1.479(3) 0.996(2) 1.01(1) 1.235(4) 1.163 1.110 1.069 1.038(4) 1.152(3) 0.882(2) 0.936(3) 1.015 1.111(4) 1.058 1.182 1.066(4) 0.847(14) 0.87 0.965 1.07 0.926(2) 0.85 1.02 1.146(5) 1.037 0.99 1.124(14) 0.920(10) 1.24 1.279(1) 1.35 0.89 0.92 1.350(10) 5.2(1) 1.01(5) 0.89 1.120 1.2170(10) 1.192(1) 1.221(10) 1.03 1.08

Source: Sharon, G., et al., J. Phys. Chem. Ref. Data, 17:Suppl. No. 1 (1988).

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ELECTRON AFFINITY

TABLE 4.4 Electron Affinities of Atoms, Molecules, and Radicals Electron affinity of an atom (molecule or radical) is defined as the energy difference between the lowest (ground) state of the neutral and the lowest state of the corresponding negative ion in the gas phase. A(g) ⫹ e⫺ ⫽ A⫺(g) Data are limited to those negative ions which, by virtue of their positive electron affinity, are stable. Uncertainty in the final data figures is given in parentheses. Calculated values are enclosed in brackets. A. Atoms Electron affinity, Atom Aluminum Antimony Arsenic Astatine Barium Bismuth Boron Bromine Calcium Carbon Cesium Chlorine Chromium Cobalt Copper Fluorine Francium Gallium Germanium Gold Hafnium Hydrogen Hydrogen-d1 deuterium Indium Iodine Iridium Iron Lanthanum Lead Lithium Molybdenum Nickel Niobium Osmium Oxygen Palladium Phosphorus Platinum Polonium

in eV 0.441(10) 1.046(5) 0.81(3) [2.8(3)] [0.15] 0.946(10) 0.277(10) 3.363590(3) 0.0185(25) 1.2629(3) 0.471626(25) 3.61269 0.666(12) 0.662(3) 1.235(5) 3.401190(4) [0.46] 0.30(15) 1.233(3) 2.30863(3) [⬇0.] 0.75195(19) 0.75459(7) 0.3(2) 3.05904(1) 1.565(8) 0.151(3) [0.5(3)] 0.364(8) 0.6180(5) 0.748(2) 1.156(10) 0.893(25) [0.2(1)] 1.4611103(7) 0.562(5) 0.7465(3) 2.128(2) [1.9(3)]

in kJ · mol⫺1 42.5(10) 100.9(5) 78.(3) [270.(30)] [14.] 91.3(10) 26.7(10) 324.5367(3) 1.78(24) 121.85(3) 45.5048(24) 348.570 64.3(12) 63.9(3) 119.2(5) 328.1638(4) [44] 29.(15) 119.0(3) 222.748(3) [⬇0.] 72.552(18) 72.807(7) 29.(2) 295.151(1) 151.0(8) 14.6(3) [48.(30)] 35.1(8) 59.63(5) 72.2(2) 111.5(10) 86.2(24) [19.(10)] 140.97523(7) 54.2(5) 72.03(3) 205.3(2) [183.(30)]

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TABLE 4.4 Electron Affinities of Atoms, Molecules, and Radicals (Continued) A. Atoms (continued) Electron affinity, Atom

in kJ · mol⫺1

in eV

Potassium Rhenium Rubidium Ruthenium Scandium Selenium Silver Sodium Strontium Sulfur Tantalum Technetium Tellurium Thallium Tin Titanium Tungsten Vanadium Yttrium Zirconium

0.50147(10) [0.15(15)] 0.48592(2) [1.05(15)] 0.188(20) 2.020670(25) 1.302(7) 0.547926(25) 0.048(6) 2.077104(1) 0.322(12) [0.55(20)] 1.9708(3) 0.2(2) 1.112(4) 0.079(14) 0.815(2) 0.525(12) 0.307(12) 0.426(14)

48.384(10) [14.(14)] 46.884(2) [101.(14)] 18.1(19) 194.9643(24) 125.6(7) 52.86666(24) 4.6(6) 200.4094(1) 31.1(12) [53.(19)] 190.15(3) 19.(19) 107.3(4) 7.6(14) 78.6(2) 50.7(12) 29.6(12) 41.1(14)

B. Molecules Electron affinity, Molecule BF3 BH3 1,4-Benzoquinone Br2 CBrF3 CF3I COS CS2 C6F6 hexafluorobenzene 1,2-C6H4(NO3)2 (also 1,3-) 1,4-C6H4(NO3)2 C6H5Br bromobenzene C6H5Cl chlorobenzene C6H5I iodobenzene C6H5NO2 nitrobenzene 1,4-C6H4(CN)NO2 Cl2 CoH2 CsCl CuO F2 FeO I2

in eV 2.65 0.038(15) 1.91(10) 2.55(10) 0.91(20) 1.57(20) 0.46(20) 0.895(20) 0.52(10) 1.65(10) 2.00(10) 1.15(11) 0.82(11) 1.41(11) 1.01(10) 1.72(10) 2.38(10) 1.450(14) 0.455(10) 1.777(6) 3.08(10) 1.493(5) 2.55(5)

in kJ · mol⫺1 256 3.7(15) 184.(10) 246.(10) 89.(19) 151.(19) 44.(19) 86.3(19) 50.(10) 159.(10) 193.(10) 111.(11) 79.(11) 136.(11) 97.(10) 166.(10) 229.(10) 139.9(13) 43.9(10) 171.5(6) 297.(10) 144.1(5) 246.(5)

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TABLE 4.4 Electron Affinities of Atoms, Molecules, and Radicals (Continued) B. Molecules (continued) Electron affinity, Molecule

in eV

IBr IrF6 KBr KCl KI LiCl LiH MoO3 NO NO2 N2O NaBr NaCl NaI NaK O2 O3 OsF6 PBr3 PCl3 PF5 POCl3 PbO PtF6 RbCl RuF6 SF4 SF6 SO2 SeF6 SeO SeO2 TeF6 TeO UF6 V4O10 WO3

2.55(10) 6.5(4) 0.642(10) 0.582(10) 0.728(10) 0.593(10) 0.342(12) 2.9(2) 0.026(5) 2.273(5) 0.22(10) 0.788(10) 0.727(10) 0.865(10) 0.465(30) 0.451(7) 2.103(3) 6.0(3) 1.59(15) 0.82(10) 0.75(15) 1.41(2) 0.722(6) 7.0(4) 0.544(10) 7.5(3) 1.5(2) 1.05(10) 1.107(8) 2.9(2) 1.456(20) 1.823(50) 3.34(17) 1.695(22) 5.1(2) 4.2(6) 3.9(2)

in kJ · mol⫺1 246.(10) 627.(40) 61.9(10) 56.1(10) 70.2(10) 54.3(10) 33.0(12) 280.(20) 2.5(5) 219.3(5) 21.(10) 76.0(10) 70.1(10) 83.5(10) 44.9(30) 43.5(7) 202.9(9) 579.(29) 153.(14) 79.(10) 72.(14) 136.(2) 69.7(6) 675.(40) 52.5(10) 724.(28) 145.(19) 101.(10) 106.8(8) 280.(19) 140.5(l9) 175.9(48) 322.(16) 163.5(21) 492.(19) 405.(60) 376.(19)

C. Radicals Electron affinity, Radical AsH2 CCl2 CF2 CH CHBr CHCl CHF

in eV 1.27(3) 1.591(10) 0.165(10) 1.238(8) 1.454(5) 1.210(5) 0.542(5)

in kJ · mol⫺1 123.(3) 153.5(10) 15.9(10) 119.4(8) 140.3(5) 117.5(5) 52.3(5)

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TABLE 4.4 Electron Affinities of Atoms, Molecules, and Radicals (Continued) C. Radicals (continued) Electron affinity, Radical

in eV

CHI CHO2 CH2 CH2S CH2 " SiH CH3 CH3CH2O ethoxide CH3O CH3S CH3SCH2 CH3Si CH3SiH2 C2F2 difluorovinylidene C2H2 vinylidene CH2 " CH vinyl C2H3O acetaldehyde enolate CH3CH2S HC # C 9 CH2 CH3CHCN C2H5O ethoxide C2H5S ethyl sulfide C3H3 propargyl radical CH3CH 9 CN C3H5 allyl C3H5O acetone enolate propionaldehyde enolate C3H5O2 methyl acetate enolate C3H7O propoxide isopropyl oxide C3H7S propyl sulfide isopropyl sulfide C4H5O cyclobutanone enolate C4H7O butyraldehyde enolate C4H9O tert-butoxyl C4H9S butyl sulfide tert-butyl sulfide C5H5 cyclopentadienyl C5H7 pentadienyl C5H7O cyclopentanone enolate C5H9O 3-pentanone enolate C5H11S pentyl sulfide C6H5 phenyl C6H5NH anilide C6H5O phenoxyl C6H5S thiophenoxide C6H5CH2 benzyl C6H5CH2O benzyl oxide C6H9O cyclohexanone enolate H2C " CH 9 CH " CH 9 CH " CH 9 CH2 heptatrienyl CN

1.42(17) 3.498(5) 0.652(6) 0.465(23) 2.010(10) 0.08(3) 1.726(33) 1.570(22) 1.861(4) 0.868(51) 0.852(10) 1.19(4) 2.255(6) 0.490(6) 0.667(24) 1.82476(12) 1.953(6) 0.893(25) 1.247(12) 1.726(33) 1.953(6) 0.893(25) 1.247(12) 0.362(19) 1.758(19) 1.621(6) 1.80(6) 1.789(33) 1.839(29) 2.00(2) 2.02(2) 1.801(8) 1.67(5) 1.912(54) 2.03(2) 2.07(2) 1.804(7) 0.91(3) 1.598(7) 1.69(5) 2.09(2) 1.096(6) 1.70(3) 2.253(6) ⱕ2.47(6) 0.912(6) 2.14(2) 1.526(10) 1.27(3) 3.862(4)

in kJ · mol⫺1 137.(17) 337.5(5) 62.9(6) 44.9(22) 193.9(10) 7.7(3) 166.5(32) 151.5(21) 179.6(4) 83.7(49) 82.2(10) 115.(4) 217.6(6) 47.3(6) 64.3(23) 176.062(12) 188.4(6) 86.2(24) 120.3(12) 166.5(31) 188.4(6) 86.2(24) 120.3(12) 34.9(18) 169.2(18) 156.4(6) 174.(6) 172.6(31) 177.4(28) 193.(2) 195.(2) 173.8(8) 161.(5) 184.5(52) 196.(2) 200.(2) 174.1(7) 88.(3) 154.2(7) 163.(5) 202.(2) 105.7(6) 164.(3) 217.4(6) ⱕ238.(6) 88.0(6) 206.(2) 147.2(10) 122.(3) 372.6(4)

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TABLE 4.4 Electron Affinities of Atoms, Molecules, and Radicals (Continued) C. Radicals (continued) Electron affinity, in eV

in kJ · mol⫺1

1.543(14) 2.69(14) 0.205(21) 2.275(6) 0.313(5) 0.338(15) 1.078(17) 2.272(6) 2.70(12) 3.609(5) 3.537(5) 0.370(4) 3.937(14) 1.194(11) 0.52(2) 2.140(8) 1.82767(2) 2.577(8) 1.028(10) 1.27(1) 1.092(10) 3.42(1) 2.285(6) 2.314344(4) 1.125(5) 2.21252(3) ⱕ2.95(10) 1.277(9) 1.124(20) 1.406(14)

148.9(14) 259.(14) 19.8(20) 219.5(6) 30.2(5) 32.6(14) 104.0(6) 219.2(6) 260.(12) 348.2(5) 341.3(5) 35.7(4) 379.9(14) 115.2(11) 50.(2) 206.5(8) 176.343(2) 248.6(8) 99.2(10) 123.(1) 105.4(10) 330.(1) 220.5(6) 223.300(4) 108.5(5) 213.475(3) 285.(10) 123.2(9) 108.4(19) 106.7(14)

Radical CNCH2 cyanomethyl CO3 CS ClO HCO HNO HO2 FO N3 NCO NCS NH NO3 NS O2Aryl OClO OH OIO PH PH2 PO PO2 SF SH SO SeH SiF3 SiH SiH2 SiH3

Source: H. Hotop and W. C. Lineberger, J. Phys. Chem. Reference Data 14:731 (1985).

4.4

ELECTRONEGATIVITY

Electronegativity ␹ is the relative attraction of an atom for the valence electrons in a covalent bond. It is proportional to the effective nuclear charge and inversely proportional to the covalent radius:

␹⫽

0.31(n ⫹ 1 ⫾ c) ⫹ 0.50 r

where n is the number of valence electrons, c is any formal valence charge on the atom and the sign before it corresponds to the sign of this charge, and r is the covalent radius. Originally the element fluorine, whose atoms have the greatest attraction for electrons, was given an arbitrary electronegativity of 4.0. A revision of Pauling’s values based on newer data assigns 3.90 to fluorine. Values in Table 4.5 refer to the common oxidation states of the elements.

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TABLE 4.5 Electronegativities of the Elements H 2.20 Li Be 0.98 1.57

B C N O F 2.04 2.55 3.04 3.44 3.90

Na Mg 0.93 1.31

Al Si P S Cl 1.61 1.90 2.19 2.58 3.16

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br 0.82 1.00 1.36 1.54 1.63 1.66 1.55 1.83 1.88 1.91 1.90 1.65 1.81 2.01 2.18 2.55 2.96 Rb Sr Y Zr 0.82 0.95 1.22 1.33

Nb 1.6

Mo Tc 2.16 2.10

Ru 2.2

Rh Pd Ag Cd In Sn Sb 2.28 2.20 1.93 1.69 1.78 1.96 2.05

Te 2.1

I 2.66

Cs Ba La 0.79 0.89 1.10

Ta 1.5

W 1.7

Os 2.2

Ir 2.2

Po 2.0

At 2.2

Fr 0.7

Ra 0.9

Re 1.9

Pt 2.2

Au 2.4

Hg 1.9

Tl 1.8

Pb 1.8

Bi 1.9

Ac 1.1

Lanthanides

Actinides

Hf 1.3

Ce Pr Nd 1.12 1.13 1.14 Th 1.3

Pa 1.5

U 1.7

Sm 1.17 Np 1.3

Pu 1.3

Gd 1.20 Am 1.3

Cm 1.3

Dy Ho Er Tm 1.22 1.23 1.24 1.25 Bk 1.3

Cf 1.3

Es 1.3

Fm 1.3

Md 1.3

Lu 1.0 No 1.3

Source: L. Pauling, The Chemical Bond, Cornell University Press, Ithaca, New York, 1967; L. C. Allen, J. Am. Chem. Soc. 111:9003 (1989); A. L. Allred, J. Inorg. Nucl. Chem. 17:215 (1961).

The greater the difference in electronegativity, the greater is the ionic character of the bond. The amount of ionic character I is given by: I ⫽ 0.46&␹A ⫺ ␹B&⫹ 0.035(␹A ⫺ ␹B)2 The bond is fully covalent when (␹A ⫺ ␹B) ⬍ 0.5 (and I ⬍ 6%).

4.5 4.5.1

BOND LENGTHS AND STRENGTHS Atom Radius

The atom radius of an element is the shortest distance between like atoms. It is the distance of the centers of the atoms from one another in metallic crystals and for these materials the atom radius is often called the metal radius. Except for the lanthanides (CN ⫽ 6), CN ⫽ 12 for the elements. The atom radii listed in Table 4.6 are taken mostly from A. Kelly and G. W. Groves, Crystallography and Crystal Defects, Addison-Wesley, Reading, Mass., 1970.

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TABLE 4.6 Atom Radii and Effective Ionic Radii of Elements Effective ionic radii, pm

Element Actinium Aluminum Americium

Antimony

Arsenic

Atom radius, pm 187.8 143.1 173

145

124.8

Astatine

Barium Berkelium

217.3

Beryllium

111.3

Bismuth

154.7

Boron

86

Bromine

Cadmium Calcium Californium

148.9 197 186(2)

Carbon Cerium

181.8

Cesium Chlorine

265

Chromium

128

Coordination number Ion charge 3⫹ 3⫹ 2⫹ 3⫹ 4⫹ 5⫹ 6⫹ 3⫺ 1⫹ 3⫹ 5⫹ 3⫺ 3⫹ 5⫹ 1⫺ 5⫹ 7⫹ 2⫹ 2⫹ 3⫹ 4⫹ 1⫺ 2⫹ 3⫺ 3⫹ 5⫹ 1⫹ 3⫹ 1⫺ 3⫹ 5⫹ 7⫹ 2⫹ 2⫹ 2⫹ 3⫹ 4⫹ 4⫺ 4⫹ 3⫹ 4⫹ 1⫹ 1⫺ 5⫹ 7⫹ 1⫹ 2⫹ 3⫹

* CN ⫽ 3

4

39

76

33.5

195 27

35 11 59 31* 78

260 15

34 8 81

6

8

12

111 53.5 97.5 89 86 80 245 89 76 60 222 58 46 227 57 62 136 118 98 87 45 213 103 76

126 109 95

142

160

93

111

27 196 47 25 95 100 117 95 82.1 16 102 87 167 181

110 112

131 135

114.3 97 174

134 114 188

27 73 LS 80 HS 61.5

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TABLE 4.6 Atom Radii and Effective Ionic Radii of Elements (Continued) Effective ionic radii, pm

Element

Atom radius, pm

Ion charge

125

4⫹ 5⫹ 6⫹ 2⫹

Chromium (continued) Cobalt

Coordination number 4 41 34.5 26 38

3⫹

Copper

128

Curium

174

Dysprosium

178.1

Einsteinium Erbium Europium

186(2) 176.1 208.4

Fluorine

71.7

Francium Gadolinium Gallium

270 180.4 135

Germanium

128

Gold

144

Hafnium Holmium Hydrogen Indium

159 176.2 167

Iodine

Iridium

135.5

Iron

126

4⫹ 1⫹ 2⫹ 3⫹ 3⫹ 4⫹ 2⫹ 3⫹ 3⫹ 3⫹ 2⫹ 3⫹ 1⫺ 7⫹ 1⫹ 3⫹ 2⫹ 3⫹ 2⫹ 4⫹ 1⫹ 3⫹ 4⫹ 3⫹ 1⫺ 1⫹ 3⫹ 1⫺ 5⫹ 7⫹ 3⫹ 4⫹ 5⫹ 2⫹

40 60 57

131

47 39.0 68 58

62

42

63 HS 3⫹ 49 HS

Lanthanum * CN ⫽ 10

183

4⫹ 6⫹ 3⫹

6 55 49 44 65 LS 74.5 HS 54.5 LS 61 HS 53 HS 77 73 54 LS 97 85 107 91.2 98 89.0 117 94.7 133 8 180 93.8 120 62.0 73 53.0 137 85 71 90.1 154 140 80.0 220 95 53 68 62.5 57 61 LS 78 HS 55 LS 64.5 HS 58.5

8

12

57 90

95 119 102.7 100.4 125 106.6

135

105.3

83 101.5*

112

92

92 HS 78 HS

25 103.2

116.0

136

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TABLE 4.6 Atom Radii and Effective Ionic Radii of Elements (Continued) Effective ionic radii, pm

Element

Atom radius, pm

Lead

175

Lithium Lutetium Magnesium Manganese

152 173.8 160 127

Coordination number Ion charge 2⫹ 4⫹ 1⫹ 3⫹ 2⫹ 2⫹

4

6

57 66 HS

119 78 76 86.1 72.0 67 LS 83 HS 58 LS 64.5 HS 53

98 59

3⫹

Mercury

151

Molybdenum

139

Neodymium

181.4

Neptunium

155

Nickel

124

Niobium

146

Nitrogen

Nobelium Osmium

Oxygen Palladium

* CN ⫽ 3 † CN ⫽ 7

135

137

4⫹ 5⫹ 6⫹ 7⫹ 1⫹ 2⫹ 3⫹ 4⫹ 5⫹ 6⫹ 2⫹ 3⫹ 2⫹ 3⫹ 4⫹ 5⫹ 6⫹ 7⫹ 2⫹ 3⫹ 4⫹ 3⫹ 4⫹ 5⫹ 3⫺ 1⫹ 3⫹ 5⫹ 2⫹ 4⫹ 5⫹ 6⫹ 7⫹ 8⫹ 2⫺ 2⫹ 3⫹ 4⫹

39 33 25.5 25 111* 96

46 41

55

48 146 25

46 119 102 69 65.0 61 59 98.3 110 101 87 75 72 71 69.0 56 LS 60 HS 48 LS 72 68 64

8

12

129 94

149

97.7 89 96

114

73† 129 110.9

127

98

79 74

16 13 110 63.0 57.5 54.5 52.5 39 138 64

140 86 76 61.5

142

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TABLE 4.6 Atom Radii and Effective Ionic Radii of Elements (Continued) Effective ionic radii, pm

Element

Atom radius, pm

Phosphorus

108

Platinum

138.5

Plutonium

159

Polonium

164

Potassium Praseodymium

232 182.4

Promethium Protoactinium

183.4 163

Radium Rhenium

(220) 137

Rhodium

134

Rubidium Ruthenium

248 134

Samarium

180.4

Scandium Selenium

162 116

Silicon Silver

118 144

Sodium Strontium Sulfur

186 215 106

Tantalum

146

Coordination number Ion charge 3⫺ 3⫹ 5⫹ 2⫹ 4⫹ 5⫹ 3⫹ 4⫹ 5⫹ 6⫹ 2⫺ 4⫹ 6⫹ 1⫹ 3⫹ 4⫹ 3⫹ 3⫹ 4⫹ 5⫹ 2⫹ 4⫹ 5⫹ 6⫹ 7⫹ 3⫹ 4⫹ 5⫹ 1⫹ 3⫹ 4⫹ 5⫹ 7⫹ 8⫹ 2⫹ 3⫹ 3⫹ 2⫺ 4⫹ 6⫹ 4⫹ 1⫹ 2⫹ 3⫹ 1⫹ 2⫹ 2⫺ 4⫹ 6⫹ 3⫹

4

17

137

38

6 212 44 38 80 62.5 57 100 86 74 71 (230) 94 67 138 99 85 97 104 90 78 63 58 55 53 66.5 60 55 152 68 62.0 56.5

8

12

96

108 151 112.6 96 109.3

164

101 91 148

170

161

172

127 107.9 87.0

124

38 36

26 100 79 67 99

12

95.8 74.5 198 50 42 40.0 115 94 75 102 118 184 37 29 72

130

118 126

139 144

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TABLE 4.6 Atom Radii and Effective Ionic Radii of Elements (Continued) Effective ionic radii, pm

Element

Atom radius, pm

Tantalum (continued) Technetium

136

Tellurium

142

Terbium

177.3

Thallium

170

Thorium Thullium

179 175.9

Tin

151

Titanium

147

Tungsten

139

Uranium

156

Vanadium

134

Xenon Ytterbium

193.3

Yttrium Zinc Zirconium

180 134 160

Coordination number Ion charge 4⫹ 5⫹ 4⫹ 5⫹ 7⫹ 2⫺ 4⫹ 6⫹ 3⫹ 4⫹ 1⫹ 3⫹ 4⫹ 2⫹ 3⫹ 2⫹ 4⫹ 2⫹ 3⫹ 4⫹ 4⫹ 5⫹ 6⫹ 3⫹ 4⫹ 5⫹ 6⫹ 2⫹ 3⫹ 4⫹ 5⫹ 8⫹ 2⫹ 3⫹ 3⫹ 2⫹ 4⫹

4

37 66 43

75

55

42

42

52

35.5 40

60 59

6 68 64 64.5 60 56 221 97 56 92.3 76 150 88.5 94 103 88.0 118 69.0 86 67.0 60.5 66 62 60 102.5 89 76 73 79 64.0 58 54 48 102 86.8 90.0 74.0 72

8

12

74

104.0 88 159 98 105

170

99.4

105*

121

81

74

100

117

86

72

114 98.5 101.9 90 84

104* 108* 89*

* CN ⫽ 11

4.5.2

Ionic Radii

One of the major factors in determining the structures of the substances that can be thought of as made up of cations and anions packed together is ionic size. It is obvious from the nature of wave functions that no ion has a precisely defined radius. However, with the insight afforded by electron

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density maps and with a large base of data, new efforts to establish tables of ionic radii have been made, the most successful being those of Shannon and Prewitt. Pertinent references: R. D. Shannon and C. T. Prewitt, Acta Crystallographica B25:925 (1969); B26:1046 (1970) and R. D. Shannon, Acta Crystallographica A32:751 (1976). Shannon and Prewitt base their effective ionic radii on the assumption that the ionic radius of O2⫺ (CN 6) is 140 pm and that of F⫺ (CN 6) is 133 pm. Also taken into consideration is the coordination number (CN) and electronic spin state (HS and LS, high spin and low spin) of firstrow transition metal ions. These radii are empirical and include effects of covalence in specific metal-oxygen or metal-fluorine bonds. Older “crystal ionic radii” were based on the radius of F⫺ (CN 6) equal to 119 pm; these radii are 14–18 percent larger than the effective ionic radii.

4.5.3

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Covalent Radii

Covalent radii (Table 4.7) are the distance between two kinds of atoms connected by a covalent bond of a given type (single, double, etc.).

TABLE 4.7 Covalent Radii for Atoms Element Aluminum Antimony Arsenic Beryllium Boron Bromine Cadmium Carbon Chlorine Copper Fluorine Gallium Germanium Hydrogen Indium Iodine Magnesium Mercury Nitrogen Oxygen Phosphorus Silicon Selenium Silver Sulfur Tellurium Tin Zinc

Single-bond radius, pm* 126 141 121 106 88 114 148 77.2 99 135 64 126 122 30 144 133 140 148 70 66 110 117 117 152 104 137 140 131

Double-bond radius, pm

Triple-bond radius, pm

131 111

104 66.7 89

60.3

54 112

123

60 55 100 107 107 94 127 130

55 93 100

87

* Single-bond radii are for a tetrahedral (CN ⫽ 4) structure.

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TABLE 4.8 Octahedral Covalent Radii for CN ⫽ 6

Atom

Octahedral covalent radius, pm

Atom

Octahedral covalent radius, pm

132 122 140 132 123 120 139

Nickel(III) Nickel(IV) Osmium(II) Palladium(IV) Platinum(IV) Rhodium(III) Ruthenium(II)

130 121 133 131 131 132 133

Cobalt(II) Cobalt(III) Gold(IV) Iridium(III) Iron(II) Iron(IV) Nickel(II)

TABLE 4.9 Bond Lengths between Carbon and Other Elements Bond type

Bond length, pm Carbon-carbon

Single bond Paraffinic: 9 C 9 C 9 In presence of 9 C " C 9 or of aromatic ring In presence of 9 C " O bond In presence of two carbon-oxygen bonds In presence of two carbon-carbon double bonds Aryl-C " O In presence of one carbon-carbon triple bond: 9 C 9 C # C 9 In presence of one carbon-nitrogen triple bond: 9 C 9 C # N In compounds with tendency to dipole formation, e.g., C " C 9 C " O In aromatic compounds In presence of carbon-carbon double and triple bonds: 9 C " C 9 C # C 9 In presence of two carbon-carbon triple bonds: 9 C # C 9 C # C 9 Double bond Single: 9 C " C 9 Conjugated with a carbon-carbon double bond: 9 C " C 9 C " C 9 Conjugated with a carbon-oxygen double bond: 9 C " C 9 C " O Cumulative: 9 C " C " C 9 or 9 C " C " O Triple bond Simple: 9 C # C 9 Conjugated: 9 C # C 9 C " C 9, 9 C # C 9 C " O, or 9 C # C 9 aryl

Bond type

154.1(3) 153(1) 151.6(5) 149(1) 142.6(5) 147(2) 146.0(3) 146.6(5) 144(1) 139.5(3) 142.6(5) 137.3(4) 133.7(6) 133.6(5) 136(1) 130.9(5) 120.4(2) 120.6(4)

Bond length, pm Carbon-halogen

Paraffinic: R 9 X Olenfinic: 9 C " C 9 X Aromatic: Ar-X Acetylenic: 9 C # C 9 X

Fluorine

Chlorine

Bromine

Iodine

137.9(5) 133.3(5) 132.8(5) (127)

176.7(2) 171.9(5) 170(1) 163.5(5)

193.8(5) 189(1) 185(1) 179.5(10)

213.9(1) 209.2(5) 205(1) 199(2)

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TABLE 4.9 Bond Lengths between Carbon and Other Elements (Continued) Bond type

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Bond length, pm Carbon-hydrogen

Paraffinic In methane (in CD4 , 109.2) In monosubstituted carbon: H 9 C 9 Y X

109.4 109.6(5)

In disubstituted carbon: H 9 C 9

107.3(5)

Y X In trisubstituted carbon: H 9 C 9 Y

107.0(7)

Z Olefinic Simple: H 9 C " C 9 Cumulative carbon-carbon double bonds: H 9 C " C " C 9 Cumulative carbon-carbon-oxygen double bonds: H 9 C 9 C " C " O Aromatic Acetylenic (in C2 H2 , 105.9) In small rings In presence of a carbon triple bond: H 9 C # C 9

108.3(5) 107(1) 108(1) 108.4(5) 105.5(5) 108.1(5) 111.5(4)

Carbon-nitrogen Single bond Paraffinic: 3-covalent nitrogen: RNH 2 , R 2 NH, R 3 N 4-covalent nitrogen: RNH⫹3 , R 3 N-BX 3 In 9 C 9 N " In aromatic compounds In conjugated heterocyclic systems (partial double bond) In 9 N 9 C " O (partial double bond) Double bond: 9 C " N 9 Triple bond (in CN radical, 117.74): 9 C # N

147.2(5) 147.9(5) 147.5(10) 143(1) 135.3(5) 132.2(5) 132 115.7(5)

Carbon-oxygen Single bond Paraffinic and saturated heterocyclic: 9 C 9 O 9 Strained, as in epoxides: 9 C 9 C 9 O In aromatic compounds, as Ar-OH Longer bond in carboxylic acids and esters (HCOOH, 131.2) In conjugated heterocyclics, as furan Double bond In CO⫹ In CO In CO⫹2 In HCO In carbonyls In aldehydes and ketones

142.6(5) 143.5(5) 136(1) 135.8(5) 137.1(16) 111.5 112.8 117.7 119.8(8) 114.5(10) 121.5(5)

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TABLE 4.9 Bond Lengths between Carbon and Other Elements (Continued) Bond type

Bond length, pm

Carbon-oxygen (continued) In acyl halides: R 9 CO 9 X Shorter bond in carboxylic acids and esters In zwitterion forms In O " C " In isocyanates: RN " C " O In conjugated systems, as in partial triple bond: O " C 9 C " C In 1,4-quinones In metal acetylacetonates In calcite: CaCO3

117.1(4) 123.3(5) 126(1) 116.0(1) 117(1) 121.5(5) 115(2) 128(2) 129(1)

Carbon-selenium Single bond Paraffinic: 9 C 9 Se 9 In presence of fluorine, as in perfluorocompounds: 9 CF 9 Se 9 Double bond In Se " C ", as SeCS and SeCO In CSe radical

198(2) 195(2) 170.9(3) 167

Carbon-silicon Alkyl substituent: H 3C 9 Si or H 2C 9 Si Aryl substituent: aryl 9 Si Electronegative substituent: R 9 Si 9 X

187.0(5) 184.3(5) 185.4(5) Carbon-sulfur

Single bond Paraffinic: 9 C 9 S 9 In presence of fluorine, as in perfluoro compounds: 9 CF 9 S 9 In heterocyclic systems: partial double bonds Double bonds In S " C; thiophene, S " CR 2 In sulfoxides and sulfones In presence of second carbon-carbon double bond: S " C 9 C " C 9 In SC radical [in CS⫹2 , 155.4(5)]

Bond type

Bond length, pm

Bond type

181.7(5) 183.5(1) 171.8(5) 171(1) 180(1) 155.5(1) 153.49(2) Bond length, pm

Other elements and carbon C-Al C-As C-B C-Be C-Bi C-Co

224(4) 198(1) 156(1) 193 230 183(2)

C-Cr C-Fe C-Ge Alkyl Aryl

192(4) 184(2) 193(3) 194.5(5)

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TABLE 4.9 Bond Lengths between Carbon and Other Elements (Continued) Bond length, pm

Bond type

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Bond length, pm

Bond type

Other elements and carbon (continued) C-Hg in Hg(CN)2 C-In C-Mo C-Ni C-Pb (alkyl) C-Pd C-Sb (paraffinic)

207(1) 199(2) 216(4) 208(4) 210.7(5) 230(1) 227(4) 220.2(16)

C-Sn Alkyl Electronegative substituent C-Te C-Tl C-W

214.3(5) 218(2) 190.4 270.5(5) 206

TABLE 4.10 Bond Lengths between Elements Other than Carbon Elements

Bond type

Bond length, pm

Elements

Boron B-B B-Br B-Cl B-F B-H B-N B-O

B2 H 6 BBr3 BCl 3 BF3 , R 2 BF Boranes Bridge Borazoles B(OH)3 , (RO)3 B

AlH AsH 3 BeH HBr CaH HCl HF GeH 4 HI KH LiH MgH NaH H 3Sb H 2Se SnH 4 DBr (2 HBr) DCl DI TBr (3 HBr) TCl

Bond length, pm

Nitrogen 177(1) 187(2) 172(1) 129(1) 121(2) 139(2) 142(1) 136(5)

N-Cl N-F N-H

N-D N-N

Hydrogen H-Al H-As H-Be H-Br H-Ca H-Cl H-F H-Ge H-I H-K H-Li H-Mg H-Na H-Sb H-Se H-Sn D-Br D-Cl D-I T-Br T-Cl

Bond type

164.6 151.9 134.3 140.8 200.2 127.4 91.7 153 160.9 224.4 159.5 173.1 188.7 170.7 146.0 170.1 141.44 127.46 161.65 141.44 127.40

N-O

N"O

N-Si

NO2Cl NF3 NH⫹4 NH 3 , RNH 2 H 2 NNH 2 R 9 CO 9 NH 2 HN " C " S ND (N 2 H) HN 3 R 2 NNH 2 N 2O N⫹2 NO2Cl RO 9 NO2 NO2 N 2O RNO2 NO⫹ SiN

179(2) 136(2) 103.4(3) 101.2 103.8 99(3) 101.3(5) 104.1 102(1) 145.1(5) 112.6(2) 111.6 124(1) 136(2) 118.8(5) 118.6(2) 122(1) 106.19 157.2

Oxygen O-H

O-O

H 2O ROH OH⫹ HOOH D2O (2 H 2O) OD HO 9 OH O⫹2 O⫺2 O22⫺

95.8 97(1) 102.89 96.0(5) 95.75 96.99 148(1) 122.7 126(2) 149(2)

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TABLE 4.10 Bond Lengths between Elements Other than Carbon (Continued) Elements

Bond type

Bond length, pm

Elements

Bond type

Oxygen (continued)

O-Al O-As O-Ba O-Cl O-Mg O-Os O-Pb

O3 AlO As2O6 bridges BaO ClO2 OCl2 MgO OsO4 PbO

127.8(5) 161.8 179 190.0 148.4 168 174.9 166 193.4

Bond length, pm

Silicon Si-Br Si-Cl Si-F Si-H Si-I Si-O Si-Si

SiBr4 , R 3SiBr SiCl 4 , R 3SiCl SiF4 , R 3SiF SiF 6 SiH 4 R 3SiH SiI 4 R 3SiI R 3SiOR H 3SiSiH 3

216(1) 201.9(5) 156.1(3) 158 148.0(5) 147.6(5) 234 246(2) 153.3(5) 230(2)

Phosphorus Sulfur P-Br P-Cl P-F P-H P-I P-N P-O

P-S

P-C

PBr3 PCl 3 PFCl 2 PH 3 , PH⫹4 PI 3 Single bond Single bond p 3 bonding sp 3 bonding p 3 bonding sp 3 bonding In rings Single bond p 3 bonding

223(1) 200(2) 155(3) 142.4(5) 252(1) 149.1 144.7 167 154(4) 212(5) 208(2) 220(3) 156.2 187(2)

S-Br S-Cl S-F S-H

S-O S-S

SOBr2 S2Cl 2 SOF2 H 2S RSH D2S SO2 SOCl 2 RSSR

227(2) 158.5(5) 158.5(5) 133.3 132.9(5) 134.5 143.21 145(2) 205(1)

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TABLE 4.11 Bond Dissociation Energies The bond dissociation energy (enthalpy change) for a bond A 9 B which is broken through the reaction AB : A ⫹ B is defined as the standard-state enthalpy change for the reaction at a specified temperature, here at 298 K. That is, ⌬Hf298 ⫽ ⌬Hf298(A) ⫹ ⌬Hf298(B) ⫺ ⌬Hf298(AB) All values refer to the gaseous state and are given at 298 K. Values of 0 K are obtained by subtracting 3⁄2RT from the value at 298 K. To convert the tabulated values to kcal/mol, divide by 4.184. ⌬Hf298 , kJ/mol

Bond Aluminum Al 9 Al Al 9 As Al 9 Au Al 9 Br Al 9 C Al 9 Cl AlCl 9 Cl AlCl 2 9 Cl AlO 9 Cl Al 9 Cu Al 9 D Al 9 F AlF 9 F AlF2 9 F AlO 9 F Al 9 H Al 9 I Al 9 Li Al 9 N Al 9 O AlCl 9 O AlF 9 O Al 9 P Al 9 Pd Al 9 S Al 9 Se Al 9 Si Al 9 Te Al 9 U

Antimony (continued) 186(9) 180 326(6) 439(8) 255 494(13) 402(8) 372(8) 515(84) 216(10) 291 664(6) 546(42) 544(46) 761(42) 285(6) 368(4) 176(15) 297(96) 512(4) 540(41) 582 213(13) 259(12) 374(8) 334(10) 251(3) 268(10) 326(29)

Antimony Sb 9 Sb Sb 9 Br Sb 9 Cl Sb 9 F Sb 9 N

⌬Hf298 , kJ/mol

Bond

299(6) 314(59) 360(50) 439(96) 301(50)

Sb 9 O Sb 9 P Sb 9 S Sb 9 Te

372(84) 357 379 277.4(38) Arsenic

As 9 As As 9 Cl As 9 Ga As 9 H As 9 N As 9 O As 9 P As 9 S As 9 Se As 9 Tl

382(11) 448 209.6(12) 272(12) 582(126) 481(8) 534(13) (478) 96 198(15) Astatine

At 9 At

(115.9) Barium

Ba 9 Br Ba 9 Cl Ba 9 F Ba 9 I Ba 9 O Ba 9 OH Ba 9 S

370(8) 444(13) 487(7) ⬎431(4) 563(42) 477(42) 400(19) Beryllium

Be 9 Be Be 9 Br Be 9 Cl

59 381(84) 388(9)

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond Beryllium (continued) BeCl 9 Cl Be 9 F Be 9 H Be 9 O Be 9 S

Bromine 540(63) 577(42) 226(21) 448(21) 372(59)

Bismuth Bi 9 Bi Bi 9 Br Bi 9 Cl Bi 9 D Bi 9 F Bi 9 Ga Bi 9 H Bi 9 O Bi 9 P Bi 9 Pb Bi 9 S Bi 9 Sb Bi 9 Se Bi 9 Te Bi 9 Tl

197(4) 267(4) 305(8) 284 259(29) 159(17) 279 343(6) 280(13) 142(15) 316(5) 251(4) 280(6) 232(11) 121(13) Boron

B9B H 3 B 9 BH 3 OB 9 BO B 9 Br B9C B 9 Cl BO 9 Cl B9D B9F BF 9 F BF2 9 F B9H B9I B9N B9O BCl 9 O B9P B9S B 9 Se B 9 Si B 9 Te

⌬Hf298 , kJ/mol

Bond

297(21) 146 506(84) 435(21) 448(29) 536(29) 460(42) 341(6) 766(13) 523(63) 557(84) 330(4) 384(21) 389(21) 806(5) 715(41) 347(17) 581(9) 462(15) 289(29) 354(20)

Br 9 Br Br 9 C Br 9 CH 3 Br 9 CH 2 Br Br 9 CHBr2 Br 9 CBr3 Br 9 CCl 3 Br 9 CF3 Br 9 CF2CF3 Br 9 CF2CF2CF3 Br 9 CHF2 Br 9 Cl Br 9 CN Br 9 CO 9 C6 H 5 Br 9 F Br 9 N Br 9 NF2 Br 9 NO Br 9 O

193.870(4) 280(21) 284(8) 255(13) 259(17) 209(13) 218(13) 285(13) 287.4(63) 278.2(63) 289 218.84(4) 381 268 233.8(2) 276(21) 222 120.1(63) 235.1(4) Cadmium

Cd 9 Cd Cd 9 Br Cd 9 Cl Cd 9 F Cd 9 H Cd 9 I Cd 9 In Cd 9 O Cd 9 S Cd 9 Se

11.3(8) 159(96) 206.7(34) 305(21) 69.0(4) 138(21) 138 142(42) 196 310 Calcium

Ca 9 Ca Ca 9 Br Ca 9 Cl Ca 9 F Ca 9 H Ca 9 I Ca 9 O Ca 9 S

14.98(46) 321(23) 398(13) 527(21) 167.8 285(63) 464(84) 314(19) Carbon

C9C H 3C 9 CH 3

607(21) 368

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TABLE 4.11 Bond Dissociation Energies (Continued)

Bond

⌬Hf298 , kJ/mol

⌬Hf298 , kJ/mol

Bond

Carbon (continued) (CH 3 )2C 9 CH 3 (CH 3 )2C 9 C(CH 3 )2 CH 3 9 C6 H 5 CH 3 9 CH 2C6H 5 (CH 3 )3C 9 C(C6 H 5 )3 CH 3 9 allyl CH 3 9 vinyl CH 3 9 C # CH CH 2 " CH 9 CH " CH 2 HC # C 9 C # CH H 2C " CH 2 HC # CH CH 3 9 CN CH 3 9 CH 2CN CH 3 9 CH(CH 3 )CN CH 3 9 C(C6 H 5 )CN(CH 3 ) CH 3CH 2 9 CH 2CN NC 9 CN C6 H 5 9 C6 H 5 CH 3 9 CF3 CH 2 F 9 CH 2 F CF3 9 CF3 CF2 " CF2 CF3 9 CN CH 3 9 CHO CH 3 9 CO CH 3CO 9 CF3 CH 3CO 9 COCH 3 C6 H 5CO 9 COC6H 5 Aryl 9 CH 2COCH 2 9 aryl C6 H 5CH 2 9 COOH (C6 H 5CH 2)2CH 9 COOH C 9 Cl C9F C9H C9I C9N CF3 9 NF2 CH 3 9 NH 2 C6 H 5CH 2 9 NH 2 CH 3 9 NHC6H 5 CH 3 9 N(CH 3 )C6 H 5 C6H 5CH 2 9 NHCH 3 C6H 5CH 2 9 N(CH 3 )2 CH 3 9 (N " NCH 3 ) C2 H 5 9 (N " NC2 H 5) (CH 3 )3C 9 N " NC(CH 3 )3 Aryl 9 CH 2N " NCH 2 9 aryl

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Carbon (continued) 335 282.4 389 301 63 301 121 490 418 628 682 962 506(21) 305(8) 331(8) 251 321.8(71) 603(21) 418 423.4(46) 368(8) 406(13) 318(13) 501 314 342.7 308.8 280(8) 277.8 273.6 284.9 248.5 397(29) 536(21) 337.2(8) 209(21) 770(4) 272(13) 331(13) 301(4) 285 272 289(4) 255(4) 219.7 209.2 182.0 157

CF3 9 (N " NCF3 ) H 2C " NH HC # N CH 3 9 NO C2 H 5 9 NO C3 H 7 9 NO (CH3 )2CH 9 NO n-C4 H 9 9 NO C6 H 5 9 NO Cl 3C 9 NO F3C 9 NO C6 F5 9 NO NC 9 NO CH 3 9 NO2 C2 H 5 9 NO2 C9O CH 3 9 OCH 3 CH 3 9 OC6 H 5 CH 3 9 OCH 2C6 H 5 C2 H 5 9 OC6 H 5 C6 H 5CH 2 9 OCOCH 3 C6 H 5CH 2 9 OCOC6 H 5 CH 3CO 9 OCH 3 CH 3 9 OSOCH 3 CH 2 " CHCH 2 9 OSOCH 3 C6 H 5CH 2 9 OSOCH 3 C"O H 2C " O OC " O SC " O C#O C9P C9S CH 3 9 SH CH 3 9 SC6 H 5 CH 3 9 SCH 2C6 H 5 OC 9 S C 9 Se

231.0 644(21) 937 174.9(38) 175.7(54) 167.8(75) 171.5(54) 215.5(42) 215.5(42) 134 130 211.3(42) 121(13) 247(13) 259 1076.5(4) 335 381 280 213 285 289 406 280 209 222 749 732 532.2(4) 628 1075 513(8) 699(8) 305(13) 285(8) 247(8) 310.4 582(96)

Cerium Ce 9 Ce Ce 9 F Ce 9 N Ce 9 O Ce 9 S Ce 9 Se Ce 9 Te

243(21) 582(42) 519(21) 795(13) 573(13) 495(15) 389(42)

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond Cesium Cs 9 Cs Cs 9 Br Cs 9 Cl Cs 9 F Cs 9 H Cs 9 I Cs 9 O Cs 9 OH

Chromium (continued) 41.75(93) 397.5(42) 439(21) 514(8) 178.1(38) 339(4) 297(25) 385(13)

Chlorine Cl 9 Cl Cl 9 C Cl 9 CH 3 Cl 9 CH⫹3 Cl 9 C(CH 3 )3 Cl 9 CH 2Cl Cl 9 CCl 3 Cl 9 CF3 Cl 9 CCl 2 F Cl 9 CClF2 Cl 9 CF2CF2 Cl 9 CH " CH 2 Cl 9 CN Cl 9 COCl Cl 9 COCH 3 Cl 9 COC6 H 5 Cl 9 Cl⫹ Cl 9 ClO O3Cl 9 ClO4 Cl 9 F O3Cl 9 F Cl 9 N Cl 9 NCl Cl 9 NCl 2 Cl 9 NF2 Cl 9 NH 2 Cl 9 NO Cl 9 NO2 Cl 9 O OCl 9 O O2Cl 9 O Cl 9 P Cl 9 SiCl 3

242.580(16) 338(42) 339(21) 213 328.4 310(13) 293(21) 360(33) 305(8) 318(8) 346.0(71) 351 439 328 349.4 310(13) 393 143.3(42) 243 250.54(8) 255 389(50) 280 381 ca. 134 251(25) 159(6) 142(4) 272(4) 243(13) 201(4) 289(42) 464 Chromium

Cr 9 Cr Cr 9 Br Cr 9 Cl

⌬Hf298 , kJ/mol

Bond

155(21) 328(24) 366(24)

Cr 9 Cu Cr 9 F Cr 9 Ge Cr 9 H Cr 9 I Cr 9 N Cr 9 O OCr 9 O O2Cr 9 O Cr 9 S

155(21) 437(20) 170(29) 280(50) 287(24) 378(19) 427(29) 531(63) 477(84) 339(21) Cobalt

Co 9 Co Co 9 Br Co 9 Cl Co 9 Cu Co 9 F Co 9 Ge Co 9 I Co 9 O Co 9 S

167(25) 331(42) 398(8) 162(17) 435(63) 239(25) 235(81) 368(21) 343(21) Copper

Cu 9 Cu Cu 9 Br Cu 9 Cl Cu 9 F Cu 9 Ga Cu 9 Ge Cu 9 H Cu 9 I Cu 9 Ni Cu 9 O Cu 9 S Cu 9 Se Cu 9 Sn Cu 9 Te

202(4) 331(25) 383(21) 431(13) 216(15) 209(21) 280(8) 197(21) 206(17) 343(63) 285(17) 293(38) 177(17) 176(38) Curium

Cm 9 O

736 Dysprosium

Dy 9 F Dy 9 O Dy 9 Se Dy 9 Te

527(21) 611(42) 322(42) 234(42)

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond

⌬Hf298 , kJ/mol

Bond

Erbium Er 9 F Er 9 O Er 9 S Er 9 Se Er 9 Te

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Gallium (continued) 565(17) 611(13) 418(42) 326(42) 239(42)

Ga 9 O Ga 9 P Ga 9 Sb Ga 9 Te

285(63) 230(13) 209(13) 251(25) Germanium

Europium Eu 9 Eu Eu 9 Cl Eu 9 F Eu 9 O Eu 9 S Eu 9 Se Eu 9 Te

33.5(165) ca. 326 528(18) 557(13) 364(15) 301(15) 243(15) Fluorine

F9F F 9 F⫹ F 9 CH 3 F 9 C(CH 3 )3 F 9 C6 H 5 F 9 CCl 3 F 9 CCl 2 F F 9 CClF2 F 9 CF3 F 9 COCH 3 F 9 FO F 9 FO2 F9N F 9 NF F 9 NF2 F 9 NO F 9 NO2

156.9(96) ⬎251 452(21) 439 485 444(21) 460(25) 490(25) 523(17) 498 272(13) 81.0 301(42) 318(25) 243(8) 235.6(42) 197(25) Gadolinium

Gd 9 F Gd 9 O Gd 9 S Gd 9 Se

590(27) 716(17) 525(15) 431(15) Gallium

Ga 9 Ga Ga 9 Br (CH 3 )3Ga 9 CH 3 Ga 9 Cl Ga 9 F Ga 9 H Ga 9 I

138(21) 444(17) 253 481(13) 577(15) ⬍274 339(10)

Ge 9 Ge Ge 9 Br Ge 9 Cl Ge 9 F Ge 9 H Ge 9 O Ge 9 S Ge 9 Se Ge 9 Si Ge 9 Te

274(21) 255(29) 431.8(4) 485(21) 321.3(8) 662(13) 551.0(25) 490(21) 301(21) 402(8) Gold

Au 9 Au Au 9 B Au 9 Be Au 9 Bi Au 9 Cl Au 9 Co Au 9 Cr Au 9 Cu Au 9 Fe Au 9 Ga Au 9 Ge Au 9 H Au 9 La Au 9 Li Au 9 Mg Au 9 Mn Au 9 Ni Au 9 Pb Au 9 Pd Au 9 Rh Au 9 S Au 9 Si Au 9 Sn Au 9 Te Au 9 U

221.3(21) 368(11) 285(8) 293(84) 343(10) 215(13) 215(6) 232(9) 187(17) 294(15) 277(15) 314(10) 80(5) 68.0(16) 243(42) 185(13) 274(21) 130(42) 143(21) 231(29) 418(25) 312(12) 244(17) 247(67) 318(29) Hafnium

Hf 9 C Hf 9 N Hf 9 O

548(63) 534(29) 791(8)

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond Hydrogen

Hydrogen (continued)

H9H H 9 2 H or H 9 D 2 H 9 2 H or D 9 D H 9 Br H9C H 9 CH H 9 CH 2 H 9 CH 3 2 H 9 C2 H 3 or D 9 CD3 H 9 C # CH H 9 CH " CH 2 H 9 CH 2CH 3 H 9 CH 2C # CH H 9 CH 2CH " CH 2 H 9 cyclopropyl H 9 CH 2CH 2CH 3 H 9 CH(CH 3 )2 H 9 cyclobutyl H 9 CH 2CH(CH 3 )2 H 9 CH(CH 3 )CH 2CH 3 H 9 C(CH 3 )3

436.002(4) 439.446(4) 443.546(4) 365.7(21) 337.2(8) 452(33) 473(4) 431(8) 442.75(25) 523(4) 427 410(4) 392.9(50) 356 423(13) 410(8) 395.4 397(13) 360 397(4) 381

H9

339(4) CH " CH2 335(4)

H 9 CH CH " CH2

H 9 CH2

CH3 414(4)

C CH3

H 9 CHCl2 H 9 CCl 3 H 9 CBr3 H 9 CCl2CHCl2 H 9 CH 2 F H 9 CHF2 H 9 CF3 H 9 CF2Cl H 9 CH 2CF3 H 9 CF2CH 3 H 9 CF2CF3 H 9 CH 2I H 9 CHI 2 H 9 CN H 9 CH 2CN H 9 CH(CH 3 )CN H 9 C(CH 3 )2CN H 9 CH 2 NH 2 H 9 CH 2Si(CH 3 )3 H 9 CH 2COCH 3 H 9 Cl H 9 CO H 9 CHO H 9 COOH H 9 COCH 3 H 9 COCH 2CH 3 H9

343(4)

H9

⌬Hf298 , kJ/mol

Bond

CH3

H 9 C(CH 3 )2CH " CH 2 H 9 cyclopentyl H 9 CH 2C(CH 3 )3 H 9 C6 H 5 H 9 CH 2C6 H 5 H 9 C(C6 H 5 )3

331 395(42) 418(4) 431 356(4) 314

H9

310

H 9 cyclohexyl H 9 cycloheptyl H 9 norbornyl H 9 CH 2Br H 9 CHBr2 H 9 CH 2Cl

399.6(42) 387.0(42) 406(13) 410(25) 435 423

O H 9 COC6 H 5 H 9 COCF3 H9F H9I H9N H 9 NH H 9 NH 2 H 9 NHCH 3 H 9 N(CH 3 )2 H 9 NHC6 H 5 H 9 N(CH 3 )C6 H 5 HNF2 H 9 N3 H 9 NO H9O H 9 OH H 9 OCH 3 H 9 OCH 2CH 3 H 9 OC(CH 3 )3 H 9 OC6 H 5 H 9 ONO

414.2 377(8) 377(8) 393(8) 423(8) 423(8) 444(13) 435(4) 446(45) 416(4) 431(63) 431(8) 431(8) 540(25) ca. 389 377(8) 364(8) 397(8) 414(4) 393(75) 431.8(4) 126(8) 364(4) 377 364(4) 364(4) 385 364(4) 381(8) 568.6(13) 298.7(8) 314(17) 377(8) 435(8) 431(8) 397(8) 335(13) 310(13) 318(13) 356 ⬍205 428.0(21) 498.7(8) 436.8(42) 436.0 439(4) 368(25) 327.6(25)

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond

Iridium

423.4(25) 374(8) 469(17) 460(17) 431(17) 343(29) 344(12) 381(4) ca. 368 305(2) 298.49(46) 393(13) 377(13) 268(2)

100(8) 418(21) 439(8) 506(15) 360(21) 197.9(85) 289(17) 152(11) 247(17) 218(17) Iodine

I9I I 9 Br I 9 CH 3 I 9 C2 H 5 I 9 CH(CH 3 )2 I 9 C(CH 3 )3 I 9 CH 2CF3 I 9 CF2CH 3 I 9 C3 F7 I 9 CH " CHCH 3 I 9 C6 H 5 I 9 C6 F5 I 9 Cl I 9 COCH 3 I 9 CN I9F I9N I 9 NO I 9 NO2 I9O

Ir 9 O Ir 9 Si

352(21) 463(21) Iron

Fe 9 Fe Fe 9 Br Fe 9 Cl Fe 9 O Fe 9 S Fe 9 Si

100(21) 247(96) ca. 352 409(13) 339(21) 297(25) Krypton

Kr 9 Kr Kr 9 F

Indium In 9 In In 9 Br In 9 Cl In 9 F In 9 O In 9 P In 9 S In 9 Sb In 9 Se In 9 Te

⌬Hf298 , kJ/mol

Bond

Hydrogen (continued) H 9 ONO2 H 9 OOH H 9 OOCCH 3 H 9 OOCCH 2CH 3 H 9 OOCC3 H 7 H9P H9S H 9 SH H 9 SCH 3 H 9 Se H 9 Si H 9 SiH 3 H 9 Si(CH 3 )3 H 9 Te

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152.549(8) 179.1(4) 232(13) 223.8 222 207.1 234(4) 216(4) 209(4) 172 268(4) 276 213.3(4) 219.7 305(4) 280(4) 159(17) 71(4) 75(4) 184(21)

5.4(8) 54 Lanthanum

La 9 La La 9 C La 9 F La 9 N La 9 O La 9 S

247(21) 506(63) 598(42) 519(42) 799(13) 577(25) Lead

Pb 9 Pb Pb 9 Br Pb(CH 3 )3 9 CH 3 Pb 9 Cl Pb 9 F Pb 9 H Pb 9 I Pb 9 O Pb 9 S Pb 9 Se Pb 9 Te

339(25) 247(38) 207(42) 301(29) 356(8) 176(21) 197(38) 378(4) 346.0(17) 303(4) 251(13) Lithium

Li 9 Li Li 9 Br Li 9 Cl Li 9 F Li 9 H Li 9 I Li 9 Na Li 9 O Li 9 OH

106(4) 423(21) 469(13) 577(21) 247 352(13) 88 341(6) 427(21)

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond Lutetium Lu 9 Lu Lu 9 F Lu 9 O Lu 9 S Lu 9 Te

⌬Hf298 , kJ/mol

Bond Molybdenum

142(34) 569(42) 695(13) 507(15) 326(17)

Mo 9 I Mo 9 O MoO 9 O MoO2 9 O

372 607(34) 678(84) 565(84) Neodymium

Magnesium Mg 9 Mg Mg 9 Br Mg 9 Cl Mg 9 F MgF 9 F Mg 9 H Mg 9 I Mg 9 O Mg 9 OH Mg 9 S

8.522(4) 297(63) 318(13) 462(21) 569(42) 197(50) ca. 285 394(35) 238(21) 310(75)

42(29) 314(10) 361(10) 423(15) 283(10) 159(17) 402(34) 301(17) 201(13) Mercury

Hg 9 Hg Hg 9 Br CH 3 9 HgCH 3 C2 H 5 9 HgC2 H 5 C3 H 7 9 HgC3 H 7 Isopropyl 9 Hgisopropyl C6 H 5 9 HgC6 H 5 Hg 9 Cl Hg 9 F Hg 9 H Hg 9 I Hg 9 K Hg 9 Na Hg 9 S Hg 9 Se Hg 9 Te

545(13) 703(34) 474(15) 385(17) 305(17) Neon

Ne 9 Ne

3.93 Neptunium

Np 9 O

Manganese Mn 9 Mn Mn 9 Br Mn 9 Cl Mn 9 F Mn 9 I Mn 9 Cu Mn 9 O Mn 9 S Mn 9 Se

Nd 9 F Nd 9 O Nd 9 S Nd 9 Se Nd 9 Te

17.2(21) 72.8(42) 240.6 182.8(42) 197.1 170.3 285 100(8) 130(38) 39.8 38 8.24(21) ⬎6.7 213 (167) (142)

720(29) Nickel

Ni 9 Ni Ni 9 Br Ni 9 Cl Ni 9 F Ni 9 H Ni 9 I Ni 9 O Ni 9 S Ni 9 Si

261.9(25) 360(13) 372(21) 435 289(13) 293(21) 391.6(38) 360(21) 318(17) Niobium

Nb 9 O

753(13) Nitrogen

N9N N 9 Br ON 9 Br N 9 Cl ON 9 Cl O2 N 9 Cl N9F FN 9 F F2 F 9 N ON 9 F O2 N 9 F

945.33(59) 276(21) 28.7(15) 389(50) 159(6) 142(4) 301(42) 318(21) 243(8) 236(4) 188(21)

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond

Oxygen (continued) 159(17) 88(4) 297(8) 271 264 213 38 480.7(42) 39.8(8) 57.3(21) 456(42) 946 630.57(13) 481 167 305 617(21) 464(21)

Osmium O3Os 9 O

301(21) Oxygen

O9O O 9 Br HO 9 CH 3 HO 9 CH " CH 2 HO 9 CH 2CH " CH 2 HO 9 C6 H 5 HO 9 CH 2C6 H 5 HO 9 CHO HO 9 COCH 3 HO 9 COC2 H 5 O 9 Cl HO 9 Cl O9F O 9 FO FO 9 OF O9I HO 9 I O9N HO 9 NCH 3 HO 9 OC(CH 3 )3 HO 9 OH O 9 OH CF3O 9 OCF3 CH 3O 9 OCH 3

⌬Hf298 , kJ/mol

Bond

Nitrogen (continued) N9I F2 N 9 NF2 H 2 N 9 NH 2 H 2 N 9 NHCH 3 H 2N 9 N(CH 3 )2 H 2N 9 NHC6 H 5 HN 9 N2 ON 9 N ON 9 NO2 O2 N 9 NO2 HN " NH N#N N9O HN " O NN 9 O ON 9 O N9P N9S

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498.34(20) 235.1(4) 377(13) 364 456 431 322 402(13) 452(21) 180 272(4) 251(13) 222(17) 467 261(84) 184(21) 234(13) 630.57(13) 209 192(8) 213.8(21) 268(4) 192 157.3(8)

C2 H 5O 9 OC2 H 5 C3 H 7O 9 OC3 H 7

159 155 Palladium

Pd 9 O

234(29) Phosphorus

P9P P 9 Br P9C P 9 Cl P9F P9H P9N P9O Br3 P " O Cl 3 P " O F3 P " O P9S P"S P 9 Se P 9 Te

490(11) 266.5 513(8) 289(42) 439(96) 343(29) 617(21) 596.6 498(21) 510(21) 544(21) 346.0(17) 347 363(10) 298(10) Platinum

Pt 9 B Pt 9 H Pt 9 O Pt 9 P Pt 9 Si

478(17) 352(38) 347(34) 417(17) 501(18) Potassium

K9K K 9 Br K 9 Cl K9F K9H K9I K 9 Na K9O K 9 OH

57.3(42) 383(8) 427(8) 497.5(25) 183(15) 331(13) 63.6(29) 239(34) 343(8) Praseodymium

Pr 9 F Pr 9 O Pr 9 S

582(46) 753(17) 492.5(46)

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond Praseodymium (continued) Pr 9 Se Pr 9 Te

446(23) 326(42) Promethium

Pm 9 F Pm 9 O Pm 9 S Pm 9 Se Pm 9 Te

540(42) 674(63) 423(63) 339(63) 255(63)

Scandium Sc 9 Sc Sc 9 Br Sc 9 C Sc 9 Cl Sc 9 F Sc 9 N Sc 9 O Sc 9 S Sc 9 Se Sc 9 Te

Radium Ra 9 Cl Rhodium 285(21) 476(21) 583.7(63) 377(63) 395(18) 391(15) Rubidium Rb 9 Rb Rb 9 Br Rb 9 Cl Rb 9 F Rb 9 H Rb 9 I Rb 9 O Rb 9 OH

45.6(21) 389(13) 448(21) 494(21) 167(21) 335(13) 255(84) 351(8) Ruthenium

Ru 9 O O3 Ru 9 O Ru 9 Si Ru 9 Th

481(63) 439 397(21) 592(42) Samarium

Sm 9 Cl Sm 9 F Sm 9 O Sm 9 S Sm 9 Se Sm 9 Te

163(21) 444(63) 393(63) 318 589(13) 469(84) 674(13) 478(13) 385(17) 289(17) Selenium

343(75)

Rh 9 Rh Rh 9 B Rh 9 C Rh 9 O Rh 9 Si Rh 9 Ti

⌬Hf298 , kJ/mol

Bond

423(13) 531(18) 619(13) 389 331(15) 272(15)

Se 9 Se Se 9 Br Se 9 C Se 9 Cl Se 9 F Se 9 H Se 9 N Se 9 O Se 9 P Se 9 S Se 9 Si Se 9 Te

332.6(4) 297(84) 582(96) 322 339(42) 305(2) 381(63) 423(13) 364(10) 381(21) 531(25) 268(8) Silicon

Si 9 Si Si 9 Br Si 9 C Si 9 Cl Si 9 F Si 9 H Si 9 I Si 9 N Si 9 O Si 9 S Si 9 Se H 3Si 9 SiH 3 (CH 3 )3Si 9 Si(CH 3 )3 (Aryl)3Si 9 Si(aryl)3 Si 9 Te

327(10) 343(50) 435(21) 456(42) 540(13) 298.49(46) 339(84) 439(38) 798(8) 619(13) 531(25) 339(17) 339 368(31) 506(38) Silver

Ag 9 Ag Ag 9 Au Ag 9 Bi

163(8) 203(9) 193(42)

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond

Tantalum 293(29) 341.4 176(8) 354(16) 180(15) 175(21) 226(8) 234(29) 176(17) 213(84) 136(21) 293(96)

Ta 9 N Ta 9 O

Te 9 B Te 9 H Te 9 I Te 9 O Te 9 P Te 9 S Te 9 Se

Strontium 332(19) 406(13) 542(7) 163(8) 263(42) 454(15) 381(42) 314(21)

Tb 9 F Tb 9 O Tb 9 S Tb 9 Te

561(42) 707(13) 515(42) 339(42) Thallium

Tl 9 Tl Tl 9 Br Tl 9 Cl Tl 9 F Tl 9 H Tl 9 I

63 333.9(17) 372.8(21) 445(19) 188(8) 272(8) Thorium

Th 9 Th Th 9 C Th 9 N Th 9 O Th 9 P

289 484(25) 577.4(21) 854(13) 377 Thullium

Sulfur S9S S 9 Cl S9F O2S 9 F S9N S9O OS 9 O O2S 9 O HS 9 SH

354(20) 268(2) 193(42) 391(8) 298(10) 339(21) 268(8) Terbium

77.0 370(13) 410(8) 481(8) 201(21) 301(8) 63.6(29) 257(17) 381(13) 59(4)

Sr 9 Br Sr 9 Cl Sr 9 F Sr 9 H Sr 9 I Sr 9 O Sr 9 OH Sr 9 S

611(84) 805(13) Tellurium

Sodium Na 9 Na Na 9 Br Na 9 Cl Na 9 F Na 9 H Na 9 I Na 9 K Na 9 O Na 9 OH Na 9 Rb

⌬Hf298 , kJ/mol

Bond

Silver (continued) Ag 9 Br Ag 9 Cl Ag 9 Cu Ag 9 F Ag 9 Ga Ag 9 Ge Ag 9 H Ag 9 I Ag 9 In Ag 9 O Ag 9 Sn Ag 9 Te

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429(6) 255 343(5) 71 464(21) 521.70(13) 551.4(84) 348.1(42) 272(21)

Tm 9 F Tm 9 O Tm 9 S Tm 9 Se Tm 9 Te

569(42) 557(13) 368(42) 276(42) 276(42) Tin

Sn 9 Sn Sn 9 Br

195(17) 339(4)

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond Tin (continued) BrSn 9 Br Br3Sn 9 Br (C2 H 5 )3Sn 9 C2 H 5 Sn 9 Cl Sn 9 F Sn 9 H Sn 9 I Sn 9 O Sn 9 S Sn 9 Se Sn 9 Te

⌬Hf298 , kJ/mol

Bond Vanadium (continued)

326 272 ca. 238 406(13) 467(13) 267(17) 234(42) 548(21) 464(3) 401.3(59) 319.2(8)

V 9 Cl V9F V9N V9O V9S V 9 Se

477(63) 590(63) 477(8) 644(21) 490(16) 347(21) Xenon

Xe 9 Xe Xe 9 F Xe 9 O

6.53(30) 13.0(4) 36.4

Titanium Ytterbium Ti 9 Ti Ti 9 Br Ti 9 C Ti 9 Cl Ti 9 F Ti 9 H Ti 9 I Ti 9 N Ti 9 O Ti 9 S Ti 9 Se Ti 9 Te

141(21) 439 435(25) 494 569(34) ca. 159 310(42) 464 662(16) 426(8) 381(42) 289(17) Tungsten

W 9 Cl W9F W9O OW 9 O O2W 9 O W9P

423(42) 548(63) 653(25) 632(84) 598(42) 305(4) Uranium

U9O OU 9 O O2 U 9 O U9S

761(17) 678(59) 644(88) 523(10) Vanadium

V9V V 9 Br V9C

242(21) 439(42) 469(63)

Yb 9 Cl Yb 9 F Yb 9 H Yb 9 O Yb 9 S

322 521(10) 159(38) 397.9(63) 167 Yttrium

Y9Y Y 9 Br Y9C Y 9 Cl Y9F Y9N Y9O Y9S Y 9 Se Y 9 Te

159(21) 485(84) 418(63) 527(42) 605(21) 481(63) 715.1(30) 528(11) 435(13) 339(13) Zinc

Zn 9 Zn Zn 9 Br C2 H 5C 9 C2 H 5 Zn 9 Cl Zn 9 F Zn 9 H Zn 9 I Zn 9 O Zn 9 S Zn 9 Se Zn 9 Te

29 142(29) ca. 201 229(20) 368(63) 85.8(21) 138(29) 284.1 205(13) 136(13) 205

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TABLE 4.11 Bond Dissociation Energies (Continued) ⌬Hf298 , kJ/mol

Bond

Bond

Zirconium Zr 9 C Zr 9 F Zr 9 N

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⌬Hf298 , kJ/mol

Zirconium (continued) 561(25) 623(63) 565(25)

Zr 9 O Zr 9 S

760(8) 575(17)

Source: T. L. Cottrell, The Strengths of Chemical Bonds, 2d ed., Butterworth, London, 1958; B. deB. Darwent, National Standard Reference Data Series, National Bureau of Standards, no. 31, Washington, 1970; S. W. Benson, J. Chem. Educ. 42:502 (1965); and J. A. Kerr, Chem. Rev. 66:465 (1966).

4.6

BOND AND GROUP DIPOLE MOMENTS

All bonds between equal atoms are given zero values. Because of their symmetry, methane and ethane molecules are nonpolar. The principle of bond moments thus requires that the CH3 group moment equal one H9 C moment. Hence the substitution of any aliphatic H by CH3 does not alter the dipole moment, and all saturated hydrocarbons have zero moments as long as the tetrahedral angles are maintained.

TABLE 4.12 Bond Dipole Moments Bond H9C Aliphatic Aromatic C9C C#C C9O Ether, aliphatic Alcohol, aliphatic C"O Aliphatic Aromatic O9H C9S C"S S9H S9O S"O Aliphatic Aromatic

Moment, D*

0.3 0.0 0.0 0.0 0.74 0.7 2.4 2.65 1.51 0.9 2.0 0.65 (0.2) 2.8 3.3

Bond C 9 N, aliphatic C"N C # N (nitrile) NC (isonitrile) N9H N9O N"O N (lone pair on sp 3 N) C 9 P, aliphatic P9O P"O P9S P"S B 9 C, aliphatic B9O Se 9 C Si 9 C Si 9 H Si 9 N

* To convert debye units D into coulomb-meters, multiply by 3.33564 ⫻ 10⫺30.

Moment, D* 0.45 1.4 3.6 3.0 1.31 0.3 2.0 1.0 0.8 (0.3) 2.7 0.5 2.9 0.7 0.25 0.7 1.2 1.0 1.55

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TABLE 4.12 Bond Dipole Moments (Continued) Bond

Moment, D*

Bond

⫺0.08 ⫺0.10 0.36 0.38 0.78 1.08 1.94 0.6 0.17 0.3 0.36 0.81 0.78 1.27 1.64 2.03 0.8 1.9 2.6 0.7 0.7 1.2 1 0.57

H 9 Sb H 9 As H9P H9I H 9 Br H 9 Cl H9F C 9 Te N9F P9I P 9 Br P 9 Cl As 9 I As 9 Br As 9 Cl As 9 F Sb 9 I Sb 9 Br Sb 9 Cl S 9 Cl Cl 9 O I 9 Br I 9 Cl Br 9 Cl

Moment, D*

Br 9 F Cl 9 F Li 9 C K 9 Cl K9F Cs 9 Cl Cs 9 F

1.3 0.88 1.4 10.6 7.3 10.5 7.9 Dative (coordination) bonds

N:B O:B S:B P:B N:O P:O S:O As : O Se : O Te : O P:S P : Se Sb : S

2.6 3.6 3.8 4.4 4.3 2.9 3.0 4.2 3.1 2.3 3.1 3.2 4.5

* To convert debye units D into coulomb-meters, multiply by 3.33564 ⫻ 10⫺30.

The group moment always includes the C9X bond. When the group is attached to an aromatic system, the moment contains the contributions through resonance of those polar structures postulated as arising through charge shifts around the ring. All values for bond and group dipole moments in Tables 4.12 and 4.13 were obtained in benzene solutions.

TABLE 4.13 Group Dipole Moments Moment, D* Group C 9 CH 3 C 9 C2 H 5 C 9 C(CH 3 )3 C 9 CH " CH 2 C 9 C # CH C9F

Aromatic C 9 X 0.37 0.37 0.5 ⬍0.4 0.7 1.47

Aliphatic C 9 X 0.0 0.0 0.0 0.6 0.9 1.79

* To convert debye units D into coulomb-meters, multiply by 3.33564 ⫻ 10⫺30.

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TABLE 4.13 Group Dipole Moments (Continued)

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Moment, D* Group C 9 Cl C 9 Br C9I C 9 CH 2 F C 9 CF3 C 9 CH 2Cl C 9 CHCl 2 C 9 CCl 3 C 9 CH 2 Br C9C#N C 9 NC C 9 CH 2CN C9C"O C 9 CHO C 9 COOH C 9 CO 9 CH 3 C 9 CO 9 OCH 3 C 9 CO 9 OC2 H 5 C 9 OH C 9 OCH 3 C 9 OCF3 C 9 OCOCH 3 C 9 OC6 H 5 C 9 CH 2OH C 9 NH 2 C 9 NHCH 3 C 9 N(CH 3 )2 C 9 NHCOCH 3 C 9 N(C6 H 5 )2 C 9 NCO C 9 N3 C 9 NO C 9 NO2 C 9 CH 2 NO2 C 9 SH C 9 SCH 3 C 9 SCF3 C 9 SCN C 9 NCS C 9 SC6 H 5 C 9 SF5 C 9 SOCF3 (C 9 )2SO2 (C 9 )2SO2CH 3 (C 9 )2SO2CF3 C 9 SeH C 9 SeCH 3 C 9 Si(CH 3 )3

Aromatic C 9 X 1.59 1.57 1.40 1.77 2.54 1.85 2.04 2.11 1.86 4.05 3.5 1.86 2.65 2.96 1.64 2.96 1.83 1.9 1.6 1.28 2.36 1.69 1.16 1.58 1.53 1.71 1.58 3.69 (0.3) 2.32 1.44 3.09 4.01 3.3 1.22 1.34 2.50 3.59 2.9 1.51 3.4 3.88 5.05 4.73 4.32 1.08 1.31 0.44

Aliphatic C 9 X 1.87 1.82 1.65 2.32 1.95 1.94 1.57 1.96 3.4 3.5 2.0 2.4 2.49 1.63 2.49 1.75 1.8 1.7 1.28

1.16 1.68 1.46 0.86 ⫺0.3 2.8

2.70 3.4 1.55 1.40 3.6 3.3 1.5

4.53

1.32 0.4

* To convert debye units D into coulomb-meters, multiply by 3.33564 ⫻ 10⫺30.

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MOLECULAR GEOMETRY

TABLE 4.14 Spatial Orientation of Common Hybrid Bonds On the assumption that the pairs of electrons in the valency shell of a bonded atom in a molecule are arranged in a definite way which depends on the number of electron pairs (coordination number), the geometrical arrangement or shape of molecules may be predicted. A multiple bond is regarded as equivalent to a single bond as far as molecular shape is concerned. Coordination Number

2

Orbitals Hybridized

Geometrical Arrangement

Minimum Radius Ratio

sp dp

Linear

p2 ds d2

Bent (angular)

sp 2 ds 2

Trigonal planar

p3 d 2p

Trigonal pyramidal

sp 2d p 2d 2

Square planar

sp 3 d 3s

Tetrahedral

d4

Tetragonal pyramidal

sp 3d d 3sp

Trigonal bipyramidal

0.155

d 2sp 3

Octahedral

0.414

d 4sp

Trigonal prism

0.155

3

4

5 6

7

d 4sp 3 8

9

12

0.225

One atom above the face of an octahedron, which is distorted chiefly by separating the atoms at the corners of this face.

0.592

Square antiprism (dodecahedral)

0.645

Cube

0.732

Formed by adding atoms beyond each of the vertical faces of a right triangular prism.

0.732

Cube-octahedron

1.000

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FIGURE 4.1 Crystal lattice types.

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TABLE 4.15 Crystal Structure Unit cells of the different lattice types in each system are illustrated in Fig. 4.1.

System Cubic Tetragonal

Orthorhombic (or rhombic)

Hexagonal or trigonal

Monoclinic

Triclinic Rhombohedral

4.8

Characteristics Three axes equal and mutually perpendicular Two equal axes and one unequal axis mutually perpendicular Three unequal axes mutually perpendicular

Three equal axes inclined at 120⬚ with a fourth axis unequal and perpendicular to the other three Two axes at an oblique angle with a third perpendicular to the other two Three unequal axes intersecting obliquely Two equal axes making equal angle with each other

Essential Symmetry

Axes in Unit Cell

Angles in Unit Cell

Four threefold axes

a⫽b⫽c

␣ ⫽ ␤ ⫽ ␥ ⫽ 90⬚

One fourfold axis

a⫽b⫽c

␣ ⫽ ␤ ⫽ ␥ ⫽ 90⬚

Three mutually perpendicular twofold axes, or two planes intersecting in a twofold axis One sixfold axis or one threefold axis

a⫽b⫽c

␣ ⫽ ␤ ⫽ ␥ ⫽ 90⬚

a⫽b⫽c

␣ ⫽ ␤ ⫽ 90⬚; ␥ ⫽ 120⬚ ␣ ⫽ ␤ ⫽ ␥ ⫽ 90⬚

One twofold axis or one plane

a⫽b⫽c

␣ ⫽ ␤ ⫽ 90⬚; ␥ ⫽ 90⬚

No planes or axes of symmetry

a⫽b⫽c

␣ ⫽ ␤ ⫽ ␥ ⫽ 90⬚

a⫽b⫽c

NUCLIDES

TABLE 4.16 Table of Nuclides Explanation of Column Headings Nuclide. Each nuclide is identified by element name and the mass number A, equal to the sum of the numbers of protons Z and neutrons N in the nucleus. The m following the mass number (for example, 69mZn) indicates a metastable isotope. An asterisk preceding the mass number indicates that the radionuclide occurs in nature. Half-life. The following abbreviations for time units are employed: y ⫽ years, d ⫽ days, h ⫽ hours, min ⫽ minutes, s ⫽ seconds, ms ⫽ milliseconds, and ns ⫽ nanoseconds. Natural abundance. The natural abundances listed are on an “atom percent” basis for the stable nuclides present in naturally occurring elements in the earth’s crust. Thermal neutron absorption cross section. Simply designated “cross section,” it represents the ease with which a given nuclide can absorb a thermal neutron (energy less than or equal to 0.025 eV) and become a different nuclide. The cross section is given here in units of barns (1 barn ⫽ 10⫺24 cm2). If the mode of reaction is other than (n,␥), it is so indicated. Major radiations. In the last column are the principal modes of disintegration and energies of the radiations in million electronvolts (MeV). Symbols used to represent the various modes of decay are:

␣, alpha particle emission ␤⫺, beta particle, negatron ␤⫹, positron ␥, gamma radiation

K, electron capture IT, isomeric transition x, X-rays of indicated element (e.g., O-x, oxygen X-rays, and the type, K or L)

For ␤⫺ and ␤⫹, values of Emax are listed. Radiation types and energies of minor importance are omitted unless useful for identification purposes. For detailed decay schemes the literature should be consulted.

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TABLE 4.16 Table of Nuclides (Continued)

Element Hydrogen

Beryllium

A

Half-life 1 2 3 7 9 10

13 14

9.965 min

Oxygen

15 19

122.2 s 26.9 s

Fluorine

18 19 20

1.8295 h

22

2.605 y

23 24

14.659 h

Aluminum

Silicon

Phosphorus

Sulfur

19.9(2) 80.1(6)

99.634(9)

1.8(1)(n, p)

26

7.1 ⫻ 105 y

27 28

2.25 min

␤⫹(2.754) ␤⫺(4.82); ␥(0.197, 1.357) 0.0095(7) 2800.(300)(n, p)

78.89(3) 10.00(1)

0.53 0.053(6) 0.17(5) 0.07(2)

92.23(2) 4.67(2) 3.10(1) 2.62 h 1.6 ⫻ 102 y

0.230(2) 0.17(1) 0.12(1) 0.107(4) 0.073(6)

100

0.16(2)

14.28 d 25.3 d

38

2.84 h

␤⫹(0.545, 1.83); K, Ne-x, ␥(1.275) ␤⫺(1.39); ␥(2.75, 1.37)

␤⫺(1.75, 1.59); ␥(0.844, 1.014) ␤⫺(0.459); ␥(1.342, 0.942, 0.401, 0.031)

␤⫺(2.865); ␥(1.778)

␤⫺(1.471); ␥(1.266) ␤⫺(0.213) ␤⫹(3.245)

2.50 min

87.51 d 5.05 min

␤⫹(0.635); K, O-x ␤⫹(2.754) ␤⫺(5.40); ␥(1.63)

␤⫹(1.16); K, Mg-x; ␥(1.809) 100

32 34 35 37

␤⫺(0.156) ␤⫹(1.190)

100

20.90 h

30 31 32 33

0.0035(1)

11.00 s

28

␤⫺(0.555)

␤⫹(0.961) 98.89(1)

100

9.45 min

␤⫺(0.0186)

3837(10)(n, ␣) 0.005(3)

5715 y

24 25 27

28 29 30 31 32

0.008(1)

1.52 ⫻ l06 y

20.3 min

Radiation (MeV)

K, ␥(0.478) 100

11 12 14

Magnesium

0.332(2) 0.000 52(1)

53.28 d

Carbon

Sodium

Cross section, barns

12.32 y

10 11

Nitrogen

Natural abundance, % 99.985(1) 0.015(1)

Boron

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95.02(9) 4.21(8)

0.55(2) 0.29(6)

␤⫺(1.710) ␤⫺(0.249)

␤⫺(0.167) ␤⫺(4.75, 1.64); ␥(3.103, 0.908) ␤⫺(1.00, 3.0); ␥(1.942, 0.196)

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TABLE 4.16 Table of Nuclides (Continued)

Element Chlorine

Argon

Potassium

A

Half-life 35 36 37 38

Scandium

Titanium

Vanadium

24.23(5)

37 39 40 41 42

35.0 d 268 y

40 42 43 44 45 47 49

Cross section, barns 43.7(4) 46.(2) 0.4

37.24 min 55.6 min

41 42 43

Calcium

75.77(5) 3.01 ⫻ 105 y

39

39 *40

Natural abundance, %

99.600(3)

93.258(4) 0.0117(1) 6.730(4)

0.64(3) 0.5(1) 2.1(2) 30.(8) 1.46(3)

12.360 h 22.3 h

96.941(18) 1.02 ⫻ 105 y 0.135(6) 2.086(12) 162.7 d 4.536 d 8.72 min

42m

61.6 s

43 44m 44 45 46m 46

3.89 h 2.442 d 3.927 h

47 48

3.341 d 1.821 d

44 45 48 49 50 51

47.3 y 3.08 h

48

16.0 d

␤⫺(4.91, 1.11, 2.77); ␥(2.168, 1.642) ␤⫺(1.91, 2.18, 3.45); ␥(1.267, 0.250, 1.52)

0.41(3) ⬇4 6.(1) 0.8(2) ⬇15

␤⫺(1.20, 2.49); ␥(1.29) ␤⫺(0.60) ␤⫺(1.312); K, Ar-x; ␥(1.461) ␤⫺(3.523, 1.97); ␥(1.525) ␤⫺(0.825, 0.45, 1.24, 1.814); ␥(0.618, 0.373, 0.39, 0.221)

␤⫺(0.257) ␤⫺(1.98, 0.684); ␥(1.297) ␤⫺(1.95, 0.89); ␥(3.084, 4.07) ␤⫹(2.82); ␥(0.438, 1.227, 1.524) ␤⫹(1.22) IT, Sc-x; ␥(0.271) ␤⫹(1.47); K, ␥(1.16)

100 19.5 s 83.81 d

27 8.(1)

␥(0.142) ␤⫺(0.357); ␥(1.12, 0.889); Ti-x ␤⫺(0.439, 0.60); ␥(0.159) ␤⫺(0.65); ␥(1.31, 1.04, 0.984) K, ␥(0.68, 0.078) ␤⫹(1.044); K, Sc-x

73.72(3) 5.41(2) 5.18(2) 5.76 min

␤⫺(0.709); K, S-x

K, Cl-x ␤⫺(0.565)

1.82 h 33 y 1.26 ⫻ 109 y

Radiation (MeV)

7.9(9) 1.9(5) 0.179(3)

␤⫺(2.14, 1.50); ␥(0.320, 0.928) ␤⫹(0.698); ␥(0.511, 0.945, 0.983, 1.312, 2.24)

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TABLE 4.16 Table of Nuclides (Continued)

Element Vanadium (cont.)

Chromium

Manganese

Iron

A

Half-life

Cobalt

Nickel

Natural abundance, %

Cross section, barns

Radiation (MeV)

49 50 51 52

330 d ⬎1.4 ⫻ 1017 y

48 50 51 52 53

21.6 h

51 52

46.2 min 5.60 d

53 54 55 56

3.7 ⫻ 106 y 312.2 d 2.5785 h

␤⫺(1.028, 1.03, 0.718); ␥(0.847, 1.81, 2.11)

52

8.275 h

␤⫹(0.804); K, Mn-x; ␥(0.169)

54 55 56 57 59

40.(20) 4.9(1)

15.(1)

27.70 d 83.79(2) 9.50(2)

5.85(4) 2.73 y 91.75(4) 2.12(1) 44.51 d

77.3 d

57 58m 58

271.77 d 9.1 h 70.88 d

59 60m 60

10.47 min 5.271 y 1.650 h

56

6.08 d

57

35.6 h

2.7(5) 13.(2) 2.6(2) 2.5(5) 13.(3)

19 58.(8) 2.0(2)

␥(0.834)

K, Mn-x

␤⫺(0.273, 0.475); ␥(1.10, 1.29) ␤⫹(1.04, 1.50); K, Fe-x; ␥(0.932, 0.480, 1.41) ␤⫹(1.46); K, Fe-x; ␥(0.847, 1.04, 1.24, 1.77, 2.60, 3.26, 2.02) K, Fe-x; ␥(0.136, 0.122) ␥(0.025) K, ␤⫹(0.474); Fe-x; ␥(0.811) ␤⫺(1.55) ␤⫺(0.318); ␥(1.173, 1.332) ␤⫺(1.22); ␥(0.842– 0.909) K, Co-x; ␥(0.158, 0.270, 0.480, 0.75, 0.812, 1.56) K, ␤⫹(0.849, 0.712); Cox, ␥(1.378, 0.0127, 1.76)

68.077(9) 26.22(1) 100 y

70.(10) ⬍10 13.3(1)

1.4(1) ⫻ 105 1.9(2) ⫻ 103 100

61

K, V-x; ␥(0.320)

0.8(1) 18.(2)

␤⫹(2.2); ␥(0.749, 1.15) ␤⫹(0.575); ␥(0.511, 0.744, 1.434)

100

56

␤⫺(2.47); ␥(1.434) K, V-x; ␥(0.116, 0.305)

4.345(13)

17.53 h

58 60 63

K, Ti-x 0.250(2) 99.750(2)

3.75 min

55

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␤⫺(0.067)

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TABLE 4.16 Table of Nuclides (Continued)

Element Nickel (cont.)

Copper

Zinc

A

Half-life 64 65

2.517 h

66

2.275 d

61

3.408 h

63 64

12.701 h

65 66 67

5.07 min 2.580 d

62

9.26 h

64 65

243.8 d

66 67 68 69m 69 71m

Gallium

Germanium

0.926(1)

Cross section, barns 1.8(1) 22.(2)

30.83(3)

27.9(2) 4.1(1) 18.8(4)

4.5(2) ⬇270 2.17(3) 1.4(1) ⫻ 102

0.46 66.(8) 1.0(2) 6.9(1) 0.87

13.76 h 56 min 3.97 h

66

9.5 h

67

3.260 d

68

1.130 h 60.108(9)

1.68(7)

39.892(9)

4.7(2)

14.10 h

73

3.120 d 2.66 h

68 69

270.8 d 1.63 d

71 72 73 74 75

11.2 d

␤⫺(2.74); ␥(1.039) ␤⫺(0.395, 0.484, 0.577); ␥(0.185, 0.092)

K, ␤⫹(0.325), Cu-x; ␥(1.116)

IT, Zn-x, ␥(0.439) ␤⫺(0.905) ␤⫺(1.45); ␥(0.386, 0.487, 0.620) ␤⫺(0.30, 0.25); ␥(0.145, 0.191)

␤⫺(1.65); ␥(0.175, 1.042) ␤⫺(0.64, 1.51, 2.52, 3.15); ␥(0.63, 2.20, 2.50) ␤⫺(1.59); ␥(0.053, 0.297) K, ␤⫹(1.02); Ga-x; ␥(0.044, 0.382) Ga, K-x ␤⫹(0.70, 1.22); ␥(1.107, 0.574) Ga-x

27.66(3) 7.73(1) 35.94(2) 1.380 h

␤⫺(0.578); ␤⫹(0.65); Nix; ␥(1.346)

␤⫹(1.84, 4.153); ␥(1.039, 2.752) K, Zn-x; ␥(0.093, 0.184, 0.300) ␤⫹(1.83); K, Zn-x; ␥(1.077)

21.1 min

66

␤⫺(2.14, 0.65, 1.020); ␥(1.48, 0.366, 1.116) ␤⫺(0.23)

K, ␤⫹(0.66); Cu-x; ␥(0.041, 0.597) 48.6(3)

46.5 h

Radiation (MeV)

␤⫹(1.220); K, Ni-x; ␥(0.283, 0.656) 69.17(3)

72

69 70 71 72

Natural abundance, %

0.9(2) 15.(1) 0.3

␤⫺(1.19); ␥(0.265, 0.419)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

4.63

PROPERTIES OF ATOMS, RADICALS, AND BONDS

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element

A

Half-life

Germanium (cont.)

77 78

1.45 h

Arsenic

71

2.70 d

72

1.083 d

73 74

80.30 d 17.78 d

75 76

1.096 d

77

38.8 h

78

91 min

Selenium

Bromine

Krypton

Cross section, barns

75 76

1.62 h 16.2 h

Radiation (MeV)

␤⫺(0.71, 1.38, 2.19); ␥(0.211, 0.215, 0.264) ␤⫺(0.95); ␥(0.277, 0.294) K, ␤⫹(0.81); Ge-x; ␥(0.175, 1.096) ␤⫹(3.339, 2.498, 1.884); K, Ge-x; ␥(0.834, 1.051) K, ␥(0.0534, 0.0133) ␤⫹(0.94); ␤⫺(0.71, 1.35); ␥(0.596, 0.635) 100

8.40 d 7.1 h

77 79 80m 80

Natural abundance, %

11.30 h

72 73 74 75 77m 77 80 81

4.0(4)

␤⫺(2.97, 2.41, 1.79); ␥(0.559, 0.657) ␤⫺(0.683); ␥(0.239, 0.250, 0.521) ␤⫺(4.21); ␥(0.614, 0.70, 1.31) K, As-x; ␥(0.046) ␤⫹(1.32); ␥(0.361, 0.067)

0.89(2)

50.(4)

7.63(6) 49.61(10)

42.(4) 0.5

119.78 d 17.5 s

18.5 min

224.(42)

2.376 d 50.69(7)

10.8

49.31(7)

2.6

4.42 h 17.66 min

K, ␥(0.265, 0.136); As-x ␥(0.162)

␤⫺(1.58); ␥(0.276, 0.290, 0.828) ␤⫹(3.03); ␥(0.287) ␤⫹(1.9, 3.68); K, Se-x; ␥(0.559, 1.86) ␥(0.239, 0.521) IT, Br-x; ␥(0.037, 0.049) ␤⫺(1.997, 1.38); K, ␤⫹(0.85), Se-x; ␥(0.617)

81 82

1.4708 d

␤⫺(0.444); ␥(0.554, 0.619, 0.776)

76 77

14.8 h 1.24 h

79

1.455 d

K, ␥(0.252) ␤⫹(1.875, 1.700, 1.550); K, Br-x; ␥(0.130, 0.147) ␤⫹(1.626); ␥(0.261, 0.398, 0.606) IT, Kr-x; ␥(0.190) K, Br-x; ␥(0.276)

81m 81 83 84 85m

13 s 2.10 ⫻ 105 y 11.5(1) 57.0(3) 4.48 h

top of rh base of rh

183.(30) 0.10

␤⫺(0.83); ␥(0.151, 0.305)

short standard long

DEAN #37261

LEFT

(McGHP)

4.64

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Krypton (cont.)

Rubidium

Strontium

Yttrium

Zirconium

A

Half-life 85 87

10.72 y 1.27 h

88

2.84 h

84

32.9 d

85 86 87 88 89

18.65 d 4.88 ⫻ 1010 y 17.7 min 15.4 min

Natural abundance, %

25.36 d 1.126 h

85 87m 88 89 90 91

64.84 d 2.795 h

␤⫺(0.894); ␤⫹(2.681); ␥(0.882) 27.83(2)

82.58(1)

92

2.71 h 4.86 h

85

2.68 h

86

14.74 h

87m 88

12.9 h 106.6 d

90 91m 91 92

2.67 d 49.71 min 58.5 d 3.54 h

93

10.2 h

86 87

16.5 h 1.73 h

88 89

83.4 d 3.27 d

91 93 95

1.5 ⫻ 106 y 64.02 d

97

16.90 h

0.5 ⬍ 20 0.10(1) 1.2(3)

␤⫺(1.775); ␥(1.08) ␤⫺(0.283) ␤⫺(5.31); ␥(1.836, 0.898) ␤⫺(1.26, 2.2, 4.49); ␥(1.032, 1.248, 2.196) K, Rb-x K, Rb-x, Sr-x; ␥(0.150, 0.231) K, Rb-x; ␥(0.514) IT, ␥(0.388)

50.52 d 29.1 y 9.5 h

85m

Radiation (MeV)

␤⫺(0.67); ␥(0.517) ␤⫺(3.49, 0.389, 1.38); ␥(0.403, 2.55) ␤⫺(2.91); ␥(0.196, 2.392)

72.17(2)

82 85m

Cross section, barns

0.0058(4) 0.42(4) 0.0097(7)

⬍7 1.4(3)

␤⫺(1.497); ␥(0.909) ␤⫺(0.546) ␤⫺(1.09, 1.36, 2.66); ␥(0.556, 0.750, 1.024) ␤⫺(0.55, 1.5); ␥(1.383) ␤⫹(2.24); K, Sr-x; ␥(0.767, 0.232, 2.124) ␤⫹(1.58, 1.15); K, Sr-x; ␥(0.504, 0.232) ␤⫹(5.24); ␥(0.307, 0.628, 1.077, 1.153, 1.921) Y-x; ␥(0.381) ␤⫺(0.76); ␥(0.898, 1.836, 2.734, 3.219) ␤⫺(2.28); ␥(2.186) Y-x; IT; ␥(0.556) ␤⫺(1.545); ␥(1.21) ␤⫺(3.64); ␥(0.448, 0.561, 0.934, 1.405) ␤⫺(2.88); ␥(0.267, 0.947, 1.918) K, Y-x; ␥(0.243, 0.612) ␤⫹(2.260); K, Y-x; ␥(0.381, 1.228) K, Y-x; ␥(0.393) K, ␤⫹(0.897); Y-x; ␥(0.909)

11.22(4)

1.2(3)

␤⫺(0.091) ␤⫺(0.366, 0.400); ␥(0.724, 0.757) ␤⫺(1.91); ␥(0.743)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

4.65

PROPERTIES OF ATOMS, RADICALS, AND BONDS

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Niobium

Molybdenum

A

Half-life 89 90

62 d

91 92m 93m 93 94m 94

700 y 10.15 d 16.1 y

95m 95 96

3.61 d 35.0 d 23.4 h

97m 97

58.1 s 1.23 h

90

5.67 h

93m

6.85 h

95 97 98 99 101 Technetium

Ruthenium

61 d 20.0 h 4.3 d 90 d 2.6 ⫻ 106 y 4.2 ⫻ 106 y 6.012 h 2.13 ⫻ 105 y 1.64 h

97

2.88 d

100

13.4(5) 2.5(3) 0.14(1)

14.6 min

95

␥(0.871) ␤⫺(0.473); ␥(0.703, 0.871) ␥(0.204, 0.236) ␤⫺(0.160); ␥(0.765) ␤⫺(0.748, 0.500); ␥(0.778, 1.091) IT; ␥(0.766) ␤⫺(1.267); ␥(0.481, 0.658) K, ␤⫹(1.085); Nb-x; ␥(0.122, 0.257) IT, Mo-x; ␥(0.264, 0.685, 1.477)

2.75 d

4.88 h

97m 97 98 99m 99

1.1

⬍7

15.92(5) 9.55(3) 24.13(7)

94

Radiation (MeV)

␤⫹(3.320); ␥(1.627) ␤⫹(1.50); K, Zr-x; ␥(0.141, 1.129, 2.186, 2.319) IT, Nb-x; ␥(0.1045, 1.205) Mo-x K, ␥(0.913, 0.934, 1.848) Nb-x 100

2.73 h

95 96

Cross section, barns

6.26 min 2.4 ⫻ 104 y

93

95m

Natural abundance, %

2.03 h 14.60 h

91m

top of rh base of rh

20

␤⫺(1.357); Tc-x; ␥(0.181, 0.366, 0.739) ␤⫺(2.23, 0.7); ␥(0.192, 0.591) ␤⫹(0.81); ␥(1.363, 1.477, 1.520) ␤⫹(4.256); ␥(0.449, 0.703, 0.850, 0.871) ␤⫹(0.71); ␥(0.204, 0.582, 0.835) K, Mo-x; ␥(0.766, 1.074) K, Mo-x; ␥(0.778, 0.813, 0.850, 1.122) K, Tc-x; ␥(0.0965) K, Mo-x ␤⫺(0.40); ␥(0.652, 0.745) IT, Tc-x; ␥(0.141, 0.143) ␤⫺(0.292) ␤⫹(1.20, 0.91); ␥(0.290, 0.336, 0.627) K, Tc-x; ␥(0.216, 0.324, 0.461)

12.6(1)

5.8(6)

short standard long

DEAN #37261

LEFT

(McGHP)

4.66

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Ruthenium (cont.)

Rhodium

Palladium

A

Half-life

101 102 103

39.27 d

105

4.44 h

Natural abundance, % 17.0(1) 31.6(2)

106

1.020 y

99m

4.7 h

99

16 d

100

20.8 h

101m

4.35 d

101

3.3 y

102m

207 d

102

2.9 y

103m 103 104m 104

4.36 min 42.3 s

105m 105

40 s 35.4 h

106m

2.18 h

Cross section, barns 5.(1) 1.2(1) ⬍20

100

29.80 s

100

3.63 d

101

8.47 h

103 105 107 108 109

16.99 d

145 800.(100) 40.(30) 1.1(3) ⫻ 104

␥(0.051, 0.097, 0.556) ␤⫺(2.44), ␥(0.358, 0.556, 1.237) IT, Rh-x; ␥(0.130) ␤⫺(0.567, 0.247); ␥(0.280, 0.306, 0.319) ␤⫺(0.92); ␥(0.222, 0.451, 0.512, 0.616, 0.717, 0.784, 1.046, 1.528) ␤⫺(3.54, 3.0, 2.4); ␥(0.512, 0.622) K, Rh-x; ␥(0.0748, 0.0840, 0.0327) K, Rh-x; ␤⫹(0.776); ␥(0.296, 0.590) K, Rh-x; ␥(0.357, 0.497)

22.33(8) 6.5 ⫻ 106 y 26.46(9) 13.5 h

␤⫺(0.12, 0.223); ␥(0.295, 0.4444, 0.497, 0.557, 0.610) ␤⫺(1.187, 0.11, 1.134); ␥(0.149, 0.263, 0.317, 0.469, 0.676, 0.724) ␤⫺(0.0394) ␤⫹(0.74); ␥(0.277, 0.341, 0.618, 1.261) ␤⫹(0.54, 0.68); ␥(0.089, 0.353, 0.528) ␤⫹(2.62, 2.07); ␥(0.446, 0.540, 0.588, 0.823, 1.553, 2.376) K, IT, Ru-x, Rh-x; ␥(0.127, 0.307, 0.545) K, Ru-x; ␥(0.127, 0.198, 0.325) ␤⫺(1.15); ␤⫹(1.29, 0.82); ␥(0.469, 0.475, 0.557, 0.628, 1.103) K, Ru-x; ␥(0.475, 0.631, 0.697, 0.767, 1.047, 1.103) IT, Rh-x, ␥(0.0.040)

56.12 min

106

Radiation (MeV)

22.(2) 1.8(2) 8.7

␤⫺(0.03) ␤⫺(1.028); Ag-x; ␥(0.088, 0.311, 0.636)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

4.67

PROPERTIES OF ATOMS, RADICALS, AND BONDS

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Palladium (cont.)

A 111m 111

Silver

Cadmium

21.4 h 1.10 h

104

69 min

105

41.29 d

106m

8.4 d

107m 107 108m 108

44.2 s 130 y 2.42 min

109 110m

249.8 d

111m 111 112

1.08 min 7.47 d 3.13 h

115

117m

51.839(7)

35

48.161(7)

91 82.(11)

3.(2)

2.228 d

3.4 h

109

4.2 h 4.9 h 1.15 h 2.805 d

␥(0.434, 0.614, 0.723) ␤⫺(1.65); ␤⫹(0.90); ␥(0.434, 0.619, 0.633) ␤⫺(0.087, 0.530); IT, ␥(0.658, 0.764, 0.885, 0.937, 1.384) K, Ag-x; ␥(0.060, 0.245) ␤⫺(1.04); ␥(0.245, 0.342) ␤⫺(3.94, 3.4); ␥(0.607, 0.617, 1.39) ␤⫹(0.302); K, Ag-x; ␥(0.093, 0.829) K, Ag-x; ␥(0.088) K, Cd-x; ␥(0.151, 0.245)

12.80(8)

2.49 h

111

␤⫹(1.7, 1.3); ␥(0.119, 0.148) ␤⫹(0.99); ␥(0.556, 0.926, 0.942) K, Pd-x; ␥(0.064, 0.280, 0.344, 0.443) K, Pd-x; ␥(0.451, 0.512, 0.717, 1.046) K, Ag-x; ␥(0.093)

462 d 48.5 min 14.1 y 9 ⫻ 1015 y 44.6 d

Radiation (MeV)

␤⫺(0.35, 0.77); ␥(0.070, 0.172, 0.391) ␤⫺(2.2); ␥(0.060, 0.245, 0.580, 0.650, 1.389, 1.459) ␤⫺(0.28); ␥(0.018)

6.52 h

117

110m 110

Cross section, barns

23.4 min

112

107

Natural abundance, %

5.5 h

103

109 111m 111 113m 113 115m

Indium

Half-life

top of rh base of rh

12.22(6)

24.(3) 20 060.(40)

␤⫺(0.59); ␥(0.264) ␤⫺(1.62); ␥(0.934, 1.29, 0.485) ␤⫺(1.11, 0.593); In-x; ␥(0.231, 0.260, 0.336, 0.492, 0.528) ␤⫺(0.72); ␥(0.159, 0.553); In-x ␤⫺(0.67, 2.2); ␥(0.221, 0.273, 0.345, 1.303) K, Cd-x; ␤⫹(0.79); ␥(0.203, 0.623) ␥(0.658, 0.885, 0.937) ␤⫹(2.22); K, Cd-x; ␥(0.658) K, Cd-x; ␥(0.171, 0.245)

short standard long

DEAN #37261

LEFT

(McGHP)

4.68

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Indium (cont.)

Tin

Antimony

A

Half-life

113m 114m 114

1.658 h 49.51 d 1.1983 min

115m

4.486 h

*115 116m

4.4 ⫻ 1014 y 54.1 min

117m

1.94 h

117

44 min

110 113 116 117m 119m 119 121m

4.1 h 115.1 d

121 123

1.128 d 129.2 d

125 127

9.63 d 2.10 h

Natural abundance, %

Cross section, barns

95.71(2)

205

14.53(11)

⬇9 1.1(1)

8.59(4)

2.(1)

13.60 d 293 d ⬇55 y

115 116m

32.1 min 1.00 h

117 118m 118 119 120 121 122

2.80 h 5.00 h 3.6 min 38.1 h 15.89 min

60.20 d

126

12.4 d

127

3.84 d

128

9.1 h

IT, In-x; ␥(0.392) IT, K, In-x; ␥(0.190) ␤⫺(1.99); K, Cd-x, ␤⫹(0.40); ␥(0.558, 0.573, 1.30) ␤⫺(0.83); K, In-x; ␥(0.336, 0.497) ␤⫺(0.495) ␤⫺(1.00); ␥(0.138, 0.417, 1.09, 1.293) ␤⫺(1.77); ␥(0.159, 0.315, 0.553) ␤⫺(0.74); ␥(0.159, 0.397, 0.553) K, In-x; ␥(0.283) K, In-x, ␥(0.392, 0.255) K, Sn-x; ␥(0.159) K, Se-x; ␥(0.239)

␤⫺(0.354); K, In-x; ␥(0.0372) ␤⫺(0.383) ␤⫺(1.42); ␥(0.160, 1.030, 1.089) ␤⫺(2.35); ␥(1.067) ␤⫺(2.42, 3.2); ␥(0.823, 1.096) ␤⫹(1.51); ␥(0.499) ␤⫹(1.16); ␥(0.407, 0.543, 0.973, 1.293) ␤⫹(0.57); ␥(0.159) ␥(0.254, 1.051, 1.280) ␤⫹(2.65); ␥(1.230) ␥(0.0239) ␤⫹(1.72); ␥(0.704, 1.171)

57.21(5)

6

42.7(9)

3.3

2.72 d

123 124

Radiation (MeV)

␤⫺(1.414); ␤⫹(1.980); ␥(0.564, 0.693, 1.141, 1.257) ␤⫺(0.61, 2.301); ␥(0.603, 0.646, 1.69, 0.723) ␤⫺(1.9); ␥(0.279, 0.415, 0.666, 0.695, 0.720) ␤⫺(0.89, 1.10, 1.50); ␥(0.252, 0.291, 0.412, 0.437, 0.686, 0.784) ␤⫺(2.3); ␥(0.215, 0.314, 0.527, 0.743, 0.754)

short standard long

DEAN #37261

(McGHP)

RIGHT

PROPERTIES OF ATOMS, RADICALS, AND BONDS

INTERACTIVE

4.69

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element

A

Half-life

Natural abundance, %

Cross section, barns

Radiation (MeV)

Antimony (cont.)

129

4.40 h

␤⫺(0.65); ␥(0.181, 0.359, 0.460, 0.545, 0.813, 0.915, 1.030)

Tellurium

116 117

2.49 h 1.03 h

119m 119

4.69 d 16.0 h

121m 121 123m 125 127m 127 129m 129

⬇154 d 16.8 d 119.7 d

␥(0.0937) ␤⫹(1.78); ␥(0.920, 1.716, 2.300) ␥(0.154, 0.271, 1.213) ␤⫹(0.627; ␥(0.644, 0.700) ␥(0.212) ␥(0.508, 0.573) ␥(0.159)

109 d 9.35 h 33.6 d 1.160 h

131m

1.35 d

Iodine

Xenon

7.139(6)

131

25.0 min

132

25.0 min

121 122 123 124

2.12 h 3.6 min 13.2 h 4.18 d

125 126

59.4 d 13.0 d

127 128 129 130

24.99 min 1.7 ⫻ 107 y 12.36 h

131

8.040 d

132

208 h

133

20.8 h

135

6.57 h

123 125

2.00 h 17.1 h

top of rh base of rh

1.6(2)

9.(1) ⫻ 102

100

6.15(10) 22.(4) 18.(3) ⬇0.7

␤⫺(0.77); ␥(0.088) ␤⫺(0.696); ␥(0.360) ␤⫺(1.60); ␥(0.460, 0.696) ␤⫺(1.453, 0.989); I-x, ␥(0.460, 0.487) ␤⫺(0.42); IT, Te-x, I-x; ␥(0.150, 0.774, 0.794, 0.852) ␤⫺(2.14, 1.69, 1.35); I-x; ␥(0.150, 0.453, 0.493) ␤⫺(0.215); ␥(0.050, 0.112, 0.228) ␤⫹(1.2); ␥(2.12) ␤⫹(3.1); ␥(0.564) K, Te-x; ␥(0.159) ␤⫹(1.54, 2.14, 0.75); ␥(0.603, 0.723, 1.691) K, Te-x; ␥(0.035) ␤⫹(1.13); ␤⫺(0.87, 1.25); ␥(0.389, 0.662) ␤⫺(2.13); ␥(0.443, 0.527) ␤⫺(0.15); ␥(0.040) ␤⫹(1.13); ␤⫺(0.87, 1.25); ␥(0.389, 0.662) ␤⫺(0.606); ␥(0.284, 0.364, 0.637) ␤⫺(0.80, 1.03, 1.2, 1.6, 2.16); ␥(0.098, 0.506, 0.523, 0.630, 0.651, 0.667, 0.723, 0.955) ␤⫺(1.24); ␥(0.511, 0.530, 0.875) ␤⫺(0.9, 1.3); ␥(0.418, 0.527, 1.132, 1.260) ␤⫹(1.51); ␥(0.149, 0.178) ␥(0.188, 0.243)

short standard long

DEAN #37261

LEFT

(McGHP)

4.70

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Xenon (cont.)

Cesium

A 127m 127 129m 129 131m 131 133m 133

1.15 min 36.4 d 8.89 d

135m 135

15.3 min 9.1 h

126

1.64 min

127

6.2 h

128 129 132 133 134m 134

Barium

Half-life

Cross section, barns

26.4(6)

22.(5)

21.2(4)

90.(10)

2.19 d 5.243 d

190.(90)

100 2.91 h 2.065 y

137

30.2 y

126 128 129m

1.65 h 2.43 d 2.17 h

28 140.(10)

8.9(5)

2.2 h

131 133m 133 135m 135 137 137m 138 139

1.396 h

140

12.75 d

142

10.7 min

␥(0.164) ␥(0.233) ␤⫺(0.346); Cs-x; ␥(0.081) ␥(0.527) ␤⫺(0.91); ␥(0.250, 0.608) ␤⫹(3.4, 3.7); ␥(0.0389, 0.491, 0.925) ␤⫹(0.65, 1.06); ␥(0.125, 0.412) ␤⫹(2.44, 2.88); ␥(0.443) ␥(0.372, 0.412) ␥(0.465, 0.630, 0.668)

3.62 min 1.336 d 6.48 d

2.3 ⫻ 106 y 13.16 d

Radiation (MeV)

␥(0.127, 0.173) ␥(0.172, 0.203, 0.375) ␥(0.040, 0.197)

11.9 d

135 136

129

Natural abundance, %

11.7 d 1.621 d 10.53 y 1.196 d

4.(1) 6.59(2) 11.23(4)

5.8 5.(1)

71.70(7)

0.41(2) 5.1

2.552 min

IT, K, Cs-x; ␥(0.127) ␤⫺(0.658, 0.089); ␥(0.563, 0.569, 0.605, 0.796) ␤⫺(0.205) ␤⫺(0.341); ␥(0.341, 0.819, 1.048) ␤⫺(0.514); K, Ba-x; ␥(0.662)

␥(0.218, 0.234, 0.258) ␥(0.273); K, Cs-x ␥(0.177, 0.182, 0.202, 1.459) ␤⫹(1.42); ␥(0.129, 0.214, 0.221) ␥(0.124, 0.216, 0.496) ␥(0.276) ␥(0.081, 0.356) IT, Ba-x; ␥(0.268) IT, K, Ba-x; ␥(0.662)

␤⫺(2.27, 2.14); K, La-x; ␥(0.166, 1.254, 1.421) ␤⫺(0.48, 1.02); ␥(0.163, 0.305, 0.537) ␤⫺(1.0, 1.1); ␥(0.231, 0.255, 0.309, 1.204)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

4.71

PROPERTIES OF ATOMS, RADICALS, AND BONDS

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Lanthanum

Cerium

A 131

59 min

132

4.8 h

133

3.91 h

134 135 136 *138 139 140 141 142

1.68 d 3.90 h 1.54 h

132 133

3.5 h 5.4 h

135

17.7 h

137m

1.43 d

137 139 140 141

Praseodymium

Natural abundance, %

Cross section, barns

6.5 min 19.5 h 8.87 min 1.06 ⫻ 1011 y 99.9098(2)

57.(6) 9.2(2) 2.7(3)

88.43(10)

0.58(4)

11.13(10)

32.50 d

1.38 d

0.97(3) 6.1(7)

144

284.6 d

1.0(1)

136 137

13.1 min 1.28 h

141 142 143 145

19.12 h 13.57 d 5.98 h

139m 141 142 143 *144 145

100

11.5 20.(3) 90.(10)

␤⫺(1.404, 1.110); K, Pr-x; ␥(0.293) ␤⫺(0.318, 0.185); K, Pr-x; ␥(0.080, 0.134)

␤⫺(2.164); ␥(1.576) ␤⫺(0.933); ␥(0.742) ␤⫺(1.80); ␥(0.073, 0.676, 0.748) ␤⫹(1.17); ␥(0.114, 0.738) ␤⫹(0.802)

5.5 h 2.49 h 2.1 ⫻ 1015 y

␤⫺(0.436, 0.581); K, Pr-x; ␥(0.145)

␤⫹(2.98); ␥(0.540, 0.552) ␤⫹(1.68); ␥(0.434, 0.514, 0.837) ␤⫹(1.65); ␥(0.304, 0.789, 1.038) ␤⫹(1.09); ␥(0.255, 1.347, 1.631)

2.1 h 4.41 h

␤⫺(1.670, 1.35) ␤⫺(2.43) ␤⫺(2.11, 2.98, 4.52) ␥(0.154, 0.182) ␤⫹(1.3); ␥(0.058, 0.131, 0.472, 0.510) ␤⫹(0.8); ␥(0.266, 0.300, 0.607) IT K, Ce-x; ␥(0.169, 0.254) ␥(0.447) ␥(0.166)

9.0 h 137.6 d

139

Radiation (MeV)

␤⫹(1.42, 1.94); ␥(0.526, 0.109, 0.366) ␤⫹(2.6, 3.2, 3.7); ␥(0.465, 0.567) ␤⫹(1.2); ␥(0.279, 0.290, 0.302) ␤⫹(2.67); ␥(0.605) ␥(0.481) ␤⫹(1.8); ␥(0.816)

142 143

138m

Neodymium

Half-life

top of rh base of rh

27.13(2) 12.18(6) 23.8(1) 8.3(6)

19.(1) 220.(10) 3.6(3) 47.(6)

short standard long

DEAN #37261

LEFT

(McGHP)

4.72

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Neodymium (cont.)

Promethium

A

Europium

17.19(9)

Cross section, barns

146 147

10.98 d

149

1.73 h

143 144 146

265 d 360 d 5.53 y

147

2.6234 y

180

41.29 d

106.(8) ⫻ 102

148m

Samarium

Half-life

Natural abundance, %

1.5(2) 440.(150)

8.4(2) ⫻ 103

⬇1000

Radiation (MeV)

␤⫺(0.805); ␥(0.091, 0.531) ␤⫺(1.03, 1.13); ␥(0.211, 0.114) K, Nd-x; ␥(0.742) K, Nd-x; ␥(0.618, 0.696) K, ␤⫺(0.795); Nd-x; ␥(0.453, 0.75) ␤⫺(0.224); ␥(0.122, 0.197) ␤⫺(0.69, 0.50, 0.40); IT, Pm-x, Sm-x; ␥(0.550, 0.630, 0.726) ␤⫺(1.02, 2.47); ␥(0.550, 0.915, 1.465) ␤⫺(1.072, 0.78); ␥(0.286, 0.591, 0.859) ␤⫺(1.6, 2.3, 1.8); ␥(0.334, 1.166, 0.132) ␤⫺(0.84); ␥(0.168, 0.275, 0.340)

148

5.37 d

149

2.212 d

150

2.68 h

151

1.183 d

142 144 145 146 *147 148 149 150 151 152 153 154 155 156

1.208 h

22.2 min 9.4 h

␤⫺(1.52); ␥(0.104) ␤⫺(0.43, 0.71); ␥(0.166, 0.204)

148 149 150m

54.5 d 93.1 d 12.8 h

150 151 152m

36 y

␤⫹(0.92); ␥(0.550, 0.630) K, Sm-x; ␥(0.277, 0.328) ␤⫺(1.013); ␥(0.334, 0.407) ␥(0.334, 0.439, 0.584)

152

153

14.(2) ⫻ 102

⬇150

␤⫹(1.0); K, Pr-x 3.1(1)

340 d 1.03 ⫻ 108 y 1.06 ⫻ 1011 y 7 ⫻ 1015 y 1016 y

1.6(1) 280.(20)

15.0(2) 11.3(1) 13.8(1) 7.4(1)

56.(4) 2.4(6) 401.(6) ⫻ 102 102.(5)

26.7(2)

206.(15) 420.(180) 7.5(3)

90 y 1.929 d 22.7(2)

47.8(5)

9000

9.30 h 11.(2) ⫻ 103

13.48 y

52.2(5)

320.(20)

␥(0.061, 0.492); K, Pm-x ␣(2.50) ␣(2.23) ␣(1.96) ␤⫺(0.076) ␤⫺(0.64, 0.69); ␥(0.103)

␤⫺(1.85); ␥(0.122, 0.841, 0.963) K, ␤⫺(1.47, 0.690); K, Gd-x, K, Sm-x; ␥(0.122, 0.344, 1.408)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

4.73

PROPERTIES OF ATOMS, RADICALS, AND BONDS

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Europium (cont.)

Gadolinium

A

Half-life

Dysprosium

Holmium

Cross section, barns

8.59 y

1.5(3) ⫻ 103

155 156

4.76 y 15.2 d

3.9(2) ⫻ 103

157

15.13 h

158

45.9 min

146 147

48.3 d 1.588 d

151 153 155 157 158 159

124 d 241.6 d 14.80(5) 15.65(3) 24.84(12)

21.86(4) 180 y

159 161 162 163 164 165 165m

144 d

72.3 d

18.9(2) 25.5(2) 24.9(2) 28.2(2) 2.33 h 1.26 min 56 min 33.0 min

167

3.1 h

166 167 168 169 170

Radiation (MeV)

␤⫺(0.27, 0.58, 0.843, 1.87); ␥(0.123, 0.723, 1.274) ␤⫺(0.15); ␥(0.087, 0.105) ␤⫺(0.30, 0.49, 1.2, 2.45); ␥(0.089, 0.646, 0.723, 0.812) ␤⫺(1.30); ␥(0.064, 0.371, 0.411) ␤⫺(2.5); ␥(0.898, 0.944, 0.977) ␤⫹(0.35); ␥(0.115, 0.155) ␤⫹(0.93); ␥(0.229, 0.370, 0.396, 0.929) ␣(2.73); ␥(0.154, 0.243) ␥(0.94, 0.103)

␤⫺(0.971); Tb-x; ␥(0.363)

1.5(7)

␥(0.944, 0.962) 100

156 159

166

61.(1) ⫻ 103 2.54(3) ⫻ 105 2.3(5)

18.56 h

158 159 160

165 166m

Erbium

Natural abundance, %

154

160 Terbium

top of rh base of rh

23.2(5) 5.7(11) ⫻ 102 8.(2) ⫻ 103 600.(150) 170.(20) 120.(10) 2000 3.5(3) ⫻ 103

␤⫺(0.57, 0.86); ␥(0.299, 0.879, 0.966) K, Tb-x; ␥(0.326)

␤⫺(1.29); Ho-x; ␥(0.095) ␥(0.108, 0.515) ␥(0.138, 0.267) ␥(0.121, 0.132, 0.253, 0.310) ␤⫺(0.31, 0.62, 0.96); ␥(0.238, 0.321, 0.347)

100 1.2 ⫻ 103 y

61 9.14(65) ⫻ 103

1.117 d 33.6(2) 22.95(15) 26.8(2)

20 7.(2) ⫻ 102 2.0(6)

9.40 d 14.9(2)

6.2(2)

Er-x; ␥(0.810, 0.712, 0.184) ␤⫺(1.855, 1.776); ␥(1.379)

␤⫺(0.35)

short standard long

DEAN #37261

LEFT

(McGHP)

4.74

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Erbium (cont.)

Thullium

Ytterbium

Lutetium

A 171

7.52 h

172

2.05 d

166

7.70 h

169 170 171 172

128.6 d 1.92 y 2.65 d

173

8.2 h

165 166

9.9 min 2.363 d

169 171 173 174 175

32.03 d

1.23 h

164

3.14 min

165

16.7 min

178 179 †179m1 †179m2 180 180m 181

106 100.(20) ⬇160

3.6(3) ⫻ 103 50.(10) 16.(2) 120

4.19 d

178

12.7(2)

3.1(2)

␤⫺(1.49); Tm-x; ␥(0.112, 0.296, 0.308) ␤⫺(0.28, 0.36); ␥(0.407, 0.610)

␤⫺(0.968, 0.884) ␤⫺(0.096); ␥(0.067) ␤⫺(1.79, 1.86); ␥(1.387, 1.466, 1.530, 1.609) ␤⫺(0.80, 0.86); ␥(0.399, 0.461) ␤⫹(1.58); ␥(1.090) ␥(0.184, 0.779, 1.273, 2.052) ␥(0.110, 0.177, 0.198)

␤⫺(0.466); Lu-x; ␥(0.396) ␤⫺(1.40); K, Lu-x; ␥(0.150) ␤⫺(0.25); ␥(0.141, 0.325, 0.352, 0.381, 0.613) ␤⫹(1.6, 3.8); ␥(0.124, 0.262, 0.740, 0.864, 0.880) ␤⫹(2.06); ␥(0.121, 0.132, 0.174, 0.204)

97.41(2)

24

3.66 h 3.8 ⫻ 1016 y 6.75 d

2100 10.(3) ⫻ 102 27.297(4) 13.629(6)

85 46

35.100(7)

13.(1)

18.7 s 25.1 d

5.519 h 42.4 d

Radiation (MeV)

␥(0.184, 0.779, 1.273, 2.052)

14.3(2) 16.12(21) 31.8(4)

1.9 h

176 177

Cross section, barns 370.(40)

100

176 177

175 176m

Hafnium

Half-life

Natural abundance, %

30.(25)

† Two different metastable states possessing the same mass number but different half-lives.

␤⫺(1.229, 1.317); Hf-x; ␥(0.0884) ␥(0.202, 0.307) ␤⫺(0.497), Hf-x; ␥(0.113, 0.208)

␥(0.161, 0.214) ␥(0.123, 0.146, 0.363, 0.454) IT, Hf-x; ␥(0.215, 0.332, 0.443) ␤⫺(0.408); Ta-x; ␥(0.133, 0.346, 0.482)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

4.75

PROPERTIES OF ATOMS, RADICALS, AND BONDS

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Hafnium (cont.)

Tantalum

Tungsten

Rhenium

A 183

1.07 h

184

4.1 h

181 182m 182

184

8.7 h

Iridium

28.43(4) 23.9 h

182m

12.7 h

189 186 188 190m

20 8.2(6) ⫻ 103

74.8 d

69.4 d

20.(1) 10.5(3) 2 ⬇3.3 37.(2) 70.(10)

37.40(2)

110

62.60(2)

74

1.58(2) 13.3(1)

⬇80 ⬇5

24 h

9.9 min

190 191

15.4 d

192 193

30.5 h

26.4(2)

41.0(3)

196

34.9 min

184

3.0 h

185 186 188

14 h 15.7 h 1.72 d

␤⫺(0.433); ␥(0.125) ␤⫺(1.315, 0.624; K, Re-x; ␥(0.072, 0.480, 0.686) ␤⫺(0.349); ␥(0.227, 0.291)

␤⫺(1.07, 0.933); K, W-x, Os-x; ␥(0.123, 0.137, 0.632, 0.768)

3.718 d

2 ⫻ 1015 y

␥(0.147, 0.172, 0.184) ␤⫺(0.25, 0.44, 0.52); ␥(0.068, 1.121) ␤⫺(0.62); ␥(0.108, 0.246, 0.304) ␤⫺(1.17); ␥(0.253, 0.414)

␤⫹(0.55, 1.74); ␥(1.121, 1.221) ␥(0.790, 0.903)

38 d

4.2 ⫻ 1010 16.94 h

Radiation (MeV)

␤⫺(1.18, 1.54); ␥(0.459, 0.784) ␤⫺(0.74, 0.85, 1.10); ␥(0.139, 0.345)

26.50(3) 14.31(1) 30.64(1)

188

*187 188

Cross section, barns

99.988(2)

5.1 d

182 183 184 185 186 187

Natural abundance, %

16.5 min 114.43 d

183

184 185 186

Osmium

Half-life

top of rh base of rh

13 3.8(6) ⫻ 102 3.(1)

␤⫺(2.12, 1.96); Os-x; ␥(0.155) ␤⫺(1.01); ␥(0.147, 0.22, 0.245)

IT, Os-x; ␥(0.187, 0.361, 0.503, 0.616)

␤⫺(0.143); Os-x; ␥(0.129) ␤⫺(1.04); Ir-x; ␥(0.139, 0.460) ␤⫺(0.84); ␥(0.126, 0.408) ␤⫹(2.3, 2.9); ␥(0.120, 0.264, 0.390) ␥(0.254, 1.829) ␥(0.137, 0.296, 0.435) ␥(0.155, 0.478, 0.633, 2.215)

short standard long

DEAN #37261

LEFT

(McGHP)

4.76

INTERACTIVE

top of rh base of rh

SECTION 4

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Iridium (cont.)

A 189 190

13.2 d 11.8 d

191 192

73.83 d

193 194

19.3 h

195m Platinum

2.35 h

188 189

10.2 d 10.89 h

194 195m 195 196 197m 197

1.573 h 18.3 h

199m 199

14.1 s 30.8 min

197 197m

Thallium

201 202 203 204

62.73(9)

116 1.5(3) ⫻ 103

␤⫺(0.672); K, Pt-x; ␥(0.316, 0.468) ␤⫺(2.25); ␥(0.294, 0.328, 0.645) ␤⫺(0.41, 0.97); ␥(0.320, 0.365, 0.433, 0.685) ␥(0.105, 0.110, 0.201, 0.285, 0.709) ␥(0.188, 0.195) K, Ir-x; ␥(0.094, 0.608, 0.721)

32.9(6)

1.2

33.8(6) 25.3(6)

28.(1) 55

⬇16

100

3.139 d

196 197m 197 199m 199 200 202 203

920

98.7(1)

7.8 s

199

200 Mercury

37.27(9)

12.5 h

2.694 d

Radiation (MeV) K, Os-x; ␥(0.245) ␥(0.187, 0.407, 0.519, 0.558, 0.605)

4.02 d

198

200m

Cross section, barns

3.9 h

187

200 Gold

Half-life

Natural abundance, %

26.5(15) ⫻ 103

18.7 h 48.4 min 0.15(1)

3150

23.8 h 2.6725 d 42.6 min 16.87(10) 23.10(16) 29.86(20)

2.1(2) ⫻ 103 ⬍60 4.9(5)

IT, Pt-x; ␥(0.099) IT, Pt-x; ␥(0.053, 0.346) ␤⫺(0.719); K, Au-x; ␥(0.191, 0.269) ␥(0.392) ␤⫺(0.90, 1.14); ␥(0.186, 0.317, 0.494, 0.549) ␥(0.136, 0.227, 0.244) IT, K, Au-x; ␥(0.130, 0.279) ␤⫺(0.961); K, Hg-x; ␥(0.412) ␤⫺(0.292, 0.250); K, Hg-x; ␥(0.158, 0.208) ␤⫺(0.56); ␥(0.111, 0.368, 0.498, 0.597, 0.760) ␤⫺(2.2); ␥(0.368, 1.225) IT, K, Hg-x; ␥(0.134) K, Au-x; ␥(0.077) ␥(0.158)

46.61 d

␤⫺(0.213); ␥(0.279)

3.040 d 12.23 d

K, Hg-x; ␥(0.135, 0.167) K, Hg-x; ␥(0.440) 29.52(1)

3.78 y

11.(1) 22.(2)

␤⫺(0.763); K, Hg-x

short standard long

DEAN #37261

(McGHP)

RIGHT

PROPERTIES OF ATOMS, RADICALS, AND BONDS

INTERACTIVE

4.77

cap height base of text

TABLE 4.16 Table of Nuclides (Continued)

Element Thallium (cont.)

Lead

Bismuth

Polonium

Astatine

A

Half-life

205 *206

4.20 min

*207 208

4.77 min 3.053 min

209 210

2.16 min 1.30 min

201 203 204m

9.33 h 2.1615 d 1.120 h

207 209 *210 *211

3.253 h 22.6 y 36.1 min

*212

10.64 h

*214

26.9 min

205 206 209 *210 212

15.31 d 6.243 d

*214

19.7 min

Natural abundance, % 70.48(1)

100

204 205

3.53 h 1.7 h

206

8.8 d

208 209

2.898 y 102 y

210 212 214 216 218

138.38 d 298 ns 0.1637 ms 145 ms 3.04 min

207

1.81 h

208

1.63 h

Cross section, barns 0.11(2)

Radiation (MeV)

␤⫺(1.53); K, Pb-x; ␥(0.803) ␤⫺(1.43); ␥(0.897) ␤⫺(1.796, 1.28, 1.52); ␥(0.277, 0.511, 0.583, 0.614) ␤⫺(1.8); ␥(1.567, 0.465) ␤⫺(1.9, 1.3); ␥(0.298, 0.798) ␥(0.331, 0.361) ␥(0.279) IT, Pb-x; ␥(0.375, 0.899, 0.912)

22.1(1)

5.013 d 1.0092 h

top of rh base of rh

0.70(1)

0.034

␤⫺(0.645) ␣(3.72) ␤⫺(1.36); ␥(0.405, 0.427, 0.832) ␤⫺(0.569, 0.28); Bi-x; ␥(0.239) ␤⫺(0.67, 0.73); ␥(0.24, 0.30, 0.352) ␥(0.703, 1.764) ␥(0.516, 0.803, 0.881) ␤⫺(1.16); ␥(0.266, 0.352) ␤⫺(2.25); ␥(0.288, 0.727, 0.786, 1.621); Tl-x; ␣(6.05, 6.09) ␤⫺(3.26); ␥(0.609, 1.120, 1.764) ␥(0.270, 0.884, 1.016) ␥(0.837, 0.850, 0.872, 1.001) ␣(5.233); ␥(0.286, 0.312, 0.807) ␣(5.116) ␣(4.88); IT, K, Bi-x; ␥(0.260, 0.896) ␣(5.304); ␥(0.803) ␣(8.784) ␣(7.686) ␣(6.778) ␣(5.18) ␣(5.76); ␥(0.168, 0.588, 0.814) ␣(5.641); K, Po-x, ␥(0.177, 0.660, 0.685, 0.845, 1.028)

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TABLE 4.16 Table of Nuclides (Continued)

Element Astatine (cont.)

Radon

Francium

Radium

Actinium

Thorium

Protactinium

A

Half-life

209

5.41 h

210

8.1 h

211

7.214 h

210

2.4 h

211

14.68 h

212 220 222

24 min 55.6 s 2.8235 d

212

20 min

220

27.4 s

221 222 223

4.8 min 14.3 min 22.0 min

*224

3.66 d

*226

1599 y

*228

5.76 y

*227

21.77 y

*228

6.15 h

226

30.6 min

228

1.913 y

Natural abundance, %

Cross section, barns

␣(5.65), K, Po-x; ␥(0.545, 0.782, 0.790) K, Po-x; ␥(0.245, 0.528, 1.181, 1.437, 1.483) ␣(5.87); K, Po-x; ␥(0.669, 0.742)

0.74(5)

12.0(5) ⬇13 36.(5) 8.8(7) ⫻ 102

1.2(2) ⫻ 102

7.54 ⫻ 104 y

231 *232 233 *234

1.063 d 1.405 ⫻ 1010 y 22.3 min 24.10 d

7.37(4) 1.5(1) ⫻ 103 1.8(5)

17.4 d

1.5(3) ⫻ 103

3.25 ⫻ 104 y

2.0(1) ⫻ 102

*231

␣(6.039); ␥(0.196, 0.458, 0.571, 0.649) ␣(5.784, 5.851); ␥(0.169, 0.250, 0.370, 0.674, 0.678, 1.363) ␣(6.260) ␣(6.288) ␣(5.49); ␥(0.510) ␣(6.41, 6.26); ␥(1.186, 1.275) ␣(6.686, 0.641, 6.582); ␥(0.106, 0.154, 0.162) ␣(6.341); ␥(0.218, 0.409) ␤⫺(0.178) ␤⫺(0.117)

*230

230

Radiation (MeV)

23.4(5)

␣(5.685, 5.45); K, Rn-x; ␥(0.241, 0.409, 0.650) ␣(4.78, 4.60); K, Rn-x; ␥(0.186, 0.262) ␥(0.0135) ␤⫺(0.045); ␣(4.95, 4.94); K, Th-x; ␥(0.084, 0.160, 0.270) ␤⫺(2.18, 1.85, 1.11); K, Th-x; ␥(0.339, 0.911, 0.969) ␣(6.337, 6.228); ␥(0.206, 0.242) ␣(5.42, 5.34, 5.18); K, Ra-x ␣(4.68, 4.62); K, Ra-x; ␥(0.068) ␤⫺(0.305, 0.218, 0.138) ␣(4.01, 3.95); ␥(0.059) ␤⫺(1.245); ␥(0.459) ␤⫺(0.198, 0.102); K, Pa-x ␤⫺(0.51); ␥(0.444, 0.455, 0.899, 0.952) ␣(5.06, 5.03, 5.01, 4.95, 4.73); K, Ac-x; ␥(0.260, 0.284, 0.300, 0.330)

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TABLE 4.16 Table of Nuclides (Continued)

Element Protactinium (cont.)

A 232

1.31 d

233

27.0 d

234m 235 Uranium

Half-life

Natural abundance, %

Cross section, barns 4.6(10) ⫻ 102

1.17 min 24.4 min

230 232 233

20.8 d 68.9 y 1.592 ⫻ 105 y

*234

2.454 ⫻ 105 y

0.0055(5)

96.(2)

*235

7.037 ⫻ 108 y

0.720(1)

95.(5)

237 *238 239

6.75 d 4.46 ⫻ 109 y 23.47 min

99.2745(15)

236 237 238 239

1.55 ⫻ 105 y 2.14 ⫻ 106 y 2.117 d 2.355 d

237 238

45.7 d 87.74 y

239

2.411 ⫻ 104 y

2.7(1) ⫻ 102

240 242

6.537 ⫻ 103 y 3.763 ⫻ 105 y

2.9(1) ⫻ 102 19.(1)

244 246

8.2 ⫻ 107 y 10.85 d

Americium

241

432.2 y

243

7370 y

Curium

242 243 244

162.8 d 28.5 y 18.11 y

Berkelium

247 249 250

1.4 ⫻ 103 y 320 d 3.217 h

Neptunium

Plutonium

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73.(2) 47.(2)

⬇100 2.7(1) 22.(2) 180 51 5.1(2) ⫻ 102

1.7(1) 600 80 ⬇20 1.3(1) ⫻ 102 15.(1)

7.(1) ⫻ 102

Radiation (MeV)

␤⫺(1.34); ␥(0.109, 0.150, 0.894, 0.969) ␤⫺(0.256, 0.15, 0.568); K,L U-x; ␥(0.300, 0.312, 0.341) ␤⫺(2.29); IT, K, U-x ␤⫺(1.4) ␣(5.89, 5.82) ␣(5.320, 5.263) ␣(4.825, 4.783); L, Th-x; ␥(0.029, 0.042, 0.055, 0.097, 0.119, 0.146, 0.164, 0.22, 0.291, 0.32) ␣(4.776, 4.723); L, Th-x; ␥(0.121) ␣(4.40, 4.37, 4.22); K,L Th-x; ␥(0.14, 0.16, 0.186, 0.20) ␣(4.196, 4.147) ␤⫺(1.21, 1.29) ␤⫺(0.49), ␥(0.104, 0.160) ␣(4.79, 4.77); K,L Pa-x ␤⫺(1.2); ␥(0.984, 1.029) ␤⫺(0.438, 0.341); ␥(0.228, 0.278) K,L Np-x ␣(5.50, 5.46); K, U-x; ␥(0.0435) ␣(5.16, 5.14, 5.11); K, U-x; ␥(0.375, 0.414, 0.129) ␣(5.168, 5.124); L, U-x ␣(4.90, 4.86); ␥(0.045, 0.103) ␣(4.59, 4.55); L, U-x ␤⫺(0.150, 0.35); ␥(0.224)

␣(5.49, 5.44); ␥(0.12, 0.14) ␣(5.277, 5.234); ␥(0.075) ␣(6.113, 6.069); L, Pu-x ␣(5.786, 5.742) ␣(5.805, 5.753); ␥(0.099, 1.526) ␣(5.532, 5.678, 5.712) ␣(5.42); ␤⫺(0.125) ␤⫺(0.74); ␥(0.989, 1.032)

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TABLE 4.16 Table of Nuclides (Continued)

Element

A

Half-life

Natural abundance, %

Cross section, barns 2.9(2) ⫻ 102 20.(2)

Radiation (MeV)

␣(5.677, 5.851, 6.014) ␣(6.118, 6.076); L, Cm-x; ␥(0.043, 0.100)

Californium

251 252

900 y 2.645 y

Einsteinium

253 254 255

20.47 d 275.7 d 40 d

186 28.(3) ⬇55

␣(6.64); ␥(0.389) ␣(6.43) ␤⫺(0.29); ␣(6.26)

Fermium

255 257

20.1 h 100.5 d

26.(3)

␣(7.023) ␣(6.519); L, Cf-x; ␥(0.179, 0.241)

Mendelevium

258 260

51.5 d 32 d

␣(6.718, 6.763); ␥(0.368)

Nobelium

255 259

3.1 min 58 min

␣(8.12, 7.93); ␥(0.187) ␣(7.52, 7.55)

Lawrencium

260 261 262

3 min 40 min 3.6 h

Source: R. B. Firestone and V. S. Shirley, eds., Table of Isotopes, 8th ed., Wiley, New York, 1997, and V. S. Shirley, ed., Table of Radioactive Isotopes, 8th ed., Wiley-Interscience, New York, 1986.

4.9

WORK FUNCTION

TABLE 4.17 Work Functions of the Elements The work function ␾ is the energy necessary to just remove an electron from the metal surface in thermoelectric or photoelectric emission. Values are dependent upon the experimental technique (vacua of 10⫺9 or 10⫺10 torr, clean surfaces, and surface conditions including the crystal face identification). Element

␾, eV

Element

Ag Al As Au B Ba Be Bi C Ca Cd Ce Co Cr Cs Cu

4.64 4.19 (3.75) 5.32 (4.75) 2.35 5.08 4.36 (5.0) 2.71 4.12 2.80 4.70 4.40 1.90 4.70

Eu Fe Ga Ge Gd Hf Hg In Ir K La Li Mg Mn Mo Na

␾, eV 2.5 4.65 4.25 5.0 3.1 3.65 4.50 4.08 5.6 2.30 3.40 3.10 3.66 3.90 4.30 2.70

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TABLE 4.17 Work Functions of the Elements (Continued)

␾, eV

Element Nb Nd Ni Os Pb Pd Po Pr Pt Rb Re Rh Ru Sb Sc Se

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␾, eV

Element

4.20 3.1 5.15 4.83 4.18 5.00 4.6 2.7 5.40 2.20 4.95 4.98 4.80 4.56 3.5 5.9

Si Sm Sn Sr Ta Tb Te Th Ti Tl U V W Y Zn Zr

4.85 2.95 4.35 2.76 4.22 3.0 4.70 3.71 4.10 4.02 3.70 4.44 4.55 3.1 4.30 4.00

Source: S. Trasatti, J. Chem. Soc. Faraday Trans. I 68:229 (1972); N. D. Lang and W. Kohn, Phys. Rev. B 3:1215 (1971).

4.10

RELATIVE ABUNDANCES OF NATURALLY OCCURRING ISOTOPES

TABLE 4.18 Relative Abundances of Naturally Occurring Isotopes

Element Aluminum Antimony Argon

Arsenic Barium

Beryllium Bismuth Boron Bromine Cadmium

Mass number

Percent

27 121 123 36 38 40 75 130 132 134 135 136 137 138 9 209 10 11 79 81 106 108 110 111

100 57.21(5) 42.79(5) 0.337(3) 0.063(1) 99.600(3) 100 0.106(2) 0.101(2) 2.42(3) 6.59(2) 7.85(4) 11.23(4) 71.70(7) 100 100 19.9(2) 80.1(2) 50.69(7) 49.31(7) 1.25(4) 0.89(2) 12.49(12) 12.80(8)

Element Cadmium

Calcium

Carbon Cerium

Cesium Chlorine Chromium

Cobalt

Mass number

Percent

112 113 114 116 40 42 43 44 46 48 12 13 136 138 140 142 133 35 37 50 52 53 54 59

24.13(14) 12.22(8) 28.7(3) 7.49(9) 96.941(18) 0.647(9) 0.135(6) 2.088(12) 0.004(3) 0.187(4) 98.89(1) 1.11(1) 0.19(1) 0.25(1) 88.43(10) 11.13(10) 100 75.77(7) 24.23(7) 4.345(13) 83.79(2) 9.50(2) 2.365(7) 100

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TABLE 4.18 Relative Abundances of Naturally Occurring Isotopes (Continued)

Element Copper Dysprosium

Erbium

Europium Fluorine Gadolinium

Gallium Germanium

Gold Hafnium

Helium Holmium Hydrogen Indium Iodine Iridium Iron

Mass number

Percent

63 65 156 158 160 161 162 163 164 162 164 166 167 168 170 151 153 19 152 154 155 156 157 158 160 69 71 70 72 73 74 76 197 174 176 177 178 179 180 4 165 1 2 113 115 127 191 193 54 56 57 58

69.17(3) 30.83(3) 0.06(1) 0.10(1) 2.34(6) 18.9(2) 25.5(2) 24.9(2) 28.2(2) 0.14(1) 1.61(2) 33.6(2) 22.95(15) 26.8(2) 14.9(2) 47.8(5) 52.2(5) 100 0.20(1) 2.18(3) 14.80(5) 20.47(4) 15.65(3) 24.84(12) 21.86(4) 60.108(9) 39.892(9) 21.23(4) 27.66(3) 7.73(1) 35.94(2) 7.44(2) 100 0.162(3) 5.206(5) 18.606(13) 27.297(4) 13.629(6) 35.100(7) 100 100 99.985(1) 0.015(1) 4.29(2) 95.71(2) 100 37.27(9) 62.73(9) 5.85(4) 91.75(4) 2.12(1) 0.26(1)

Element Krypton

Lanthanum Lead

Lithium Lutetium Magnesium

Manganese Mercury

Molybdenum

Neodymium

Neon

Nickel

Niobium Nitrogen

Mass number

Percent

78 80 82 83 84 86 138 139 204 206 207 208 6 7 175 176 24 25 26 55 196 198 199 200 201 202 204 92 94 95 96 97 98 100 142 143 144 145 146 148 150 20 21 22 58 60 61 62 64 93 14 15

0.35(2) 2.25(2) 11.6(1) 11.5(1) 57.0(3) 17.3(2) 0.0902(2) 99.9098(2) 1.4(1) 24.1(1) 22.1(1) 52.4(1) 7.5(2) 92.5(2) 97.41(2) 2.59(2) 78.99(3) 10.00(1) 11.01(2) 100 0.15(1) 9.97(8) 16.87(10) 23.10(16) 13.18(8) 29.86(20) 6.87(4) 14.84(4) 9.25(3) 15.92(5) 16.68(5) 9.55(3) 24.13(7) 9.63(3) 27.13(12) 12.18(6) 23.80(12) 8.30(6) 17.19(9) 5.76(3) 5.64(3) 90.48(3) 0.27(1) 9.25(3) 68.077(9) 26.223(8) 1.140(1) 3.634(2) 0.926(1) 100 99.634(9) 0.366(9)

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TABLE 4.18 Relative Abundances of Naturally Occurring Isotopes (Continued)

Element Osmium

Oxygen

Palladium

Phosphorus Platinum

Potassium

Praseodymium Protoactinium Rhenium Rhodium Rubidium Ruthenium

Samarium

Scandium Selenium

Mass number

Percent

184 186 187 188 189 190 192 16 17 18 102 104 105 106 108 110 31 190 192 194 195 196 198 39 40 41 141 230 185 187 103 85 87 96 98 99 100 101 102 104 144 147 148 149 150 152 154 45 74 76 77

0.020(3) 1.58(2) 1.6(4) 13.3(1) 16.1(1) 26.4(2) 41.0(3) 99.76(1) 0.04 0.20(1) 1.02(1) 11.14(8) 22.33(8) 27.33(3) 26.46(9) 11.72(9) 100 0.01(1) 0.79(6) 32.9(6) 33.8(6) 25.3(6) 7.2(2) 93.258(4) 0.0117(1) 6.730(3) 100 100 37.40(2) 62.60(2) 100 72.17(2) 27.83(2) 5.52(6) 1.88(6) 12.7(1) 12.6(1) 17.0(1) 31.6(2) 18.7(2) 3.1(1) 15.0(2) 11.3(1) 13.8(1) 7.4(1) 26.7(2) 22.7(2) 100 0.89(2) 9.36(11) 6.63(6)

Element

Silicon

Silver Sodium Strontium

Sulfur

Tantalum Tellurium

Terbium Thallium Thorium Thullium Tin

Titanium

Tungsten

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Mass number

Percent

78 80 82 28 29 30 107 109 23 84 86 87 88 32 33 34 36 180 181 120 122 123 124 125 126 128 130 159 203 205 228 169 112 114 115 116 117 118 119 120 122 124 46 47 48 49 50 180 182 183 184

23.78(9) 49.61(10) 8.73(6) 92.23(2) 4.67(2) 3.10(1) 51.839(7) 48.161(7) 100 0.56(1) 9.86(1) 7.00(1) 82.58(1) 95.02(9) 0.75(4) 4.21(8) 0.02(1) 0.012(2) 99.988(2) 0.096(2) 2.603(4) 0.908(2) 4.816(6) 7.139(6) 18.952(11) 31.687(11) 33.799(10) 100 29.52(1) 70.48(1) 100 100 0.97(1) 0.65(1) 0.34(1) 14.53(11) 7.68(7) 24.23(11) 8.59(4) 32.59(10) 4.63(3) 5.79(5) 8.25(3) 7.44(2) 73.72(3) 5.41(2) 5.4(1) 0.12(1) 26.50(3) 14.31(1) 30.64(1)

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TABLE 4.18 Relative Abundances of Naturally Occurring Isotopes (Continued)

Element Tungsten (cont.) Uranium

Vanadium Xenon

Ytterbium

Mass number

Percent

186 234 235 238 50 51 124 126 128 129 130 131 132 134 136 168 170

28.43(4) 0.0055(5) 0.720(1) 99.275(2) 0.250(2) 99.750(2) 0.10(1) 0.09(1) 1.91(3) 26.4(6) 4.1(1) 21.2(4) 26.9(5) 10.4(2) 8.9(1) 0.13(1) 3.05(6)

Element

Yttrium Zinc

Zirconium

Mass number 171 172 173 174 176 89 64 66 67 68 70 90 91 92 94 96

Percent 14.3(2) 21.9(3) 16.12(2) 31.8(4) 12.7(2) 100 48.6(3) 27.9(2) 4.1(1) 18.8(4) 0.6(1) 51.45(3) 11.22(4) 17.15(2) 17.38(4) 2.80(2)

Source: A. H. Wapstra and G. Audi, “The 1983 Atomic Mass Evaluation,” Nucl. Phys., A432:1-54 (1985) and references cited for Table 4.16.

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PHYSICAL PROPERTIES 5.1

SOLUBILITIES Table 5.1 Solubility of Gases in Water Table 5.2 Solubilities of Inorganic Compounds and Metal Salts of Organic Acids in Water at Various Temperatures 5.2 VAPOR PRESSURES Table 5.3 Vapor Pressure of Mercury Table 5.4 Vapor Pressure of Ice in Millimeters of Mercury Table 5.5 Vapor Pressure of Liquid Ammonia, NH 3 Table 5.6 Vapor Pressure of Water Table 5.7 Vapor Pressure of Deuterium Oxide 5.2.1 Vapor-Pressure Equations Table 5.8 Vapor Pressures of Various Inorganic Compounds Table 5.9 Vapor Pressures of Various Organic Compounds 5.3 BOILING POINTS Table 5.10 Boiling Points of Water Table 5.11 Binary Azeotropic (Constant-Boiling) Mixtures Table 5.12 Ternary Azeotropic Mixtures 5.4 FREEZING MIXTURES Table 5.13 Compositions of Aqueous Antifreeze Solutions 5.4.1 Propylene Glycol– Glycerol 5.5 DENSITY AND SPECIFIC GRAVITY Table 5.14 Density of Mercury and Water Table 5.15 Specific Gravity of Air at Various Temperatures 5.5.1 Density of Moist Air 5.5.2 Specific Gravity Corrections for the Buoyant Effect of Air 5.6 VISCOSITY, SURFACE TENSION, DIELECTRIC CONSTANT, DIPOLE MOMENT, AND REFRACTIVE INDEX Table 5.16 Viscosity and Surface Tension of Various Organic Substances Table 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances Table 5.18 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances Table 5.19 Refractive Index, Viscosity, Dielectric Constant, and Surface Tension of Water at Various Temperatures 5.6.1 Refractive Index Table 5.20 Atomic and Group Refractions 5.6.2 Surface Tension 5.6.3 Dipole Moments 5.6.4 Dielectric Constants 5.6.5 Viscosity Table 5.21 Aqueous Glycerol Solutions Table 5.22 Aqueous Sucrose Solutions 5.7 COMBUSTIBLE MIXTURES Table 5.23 Properties of Combustible Mixtures in Air 5.8 THERMAL CONDUCTIVITY Table 5.24 Thermal Conductivities of Gases as a Function of Temperature Table 5.25 Liquid Thermal Conductivity of Various Substances Table 5.26 Thermal Conductivity of Various Solids

5.1

5.3 5.3 5.9 5.24 5.24 5.26 5.27 5.28 5.29 5.30 5.31 5.39 5.57 5.57 5.58 5.77 5.83 5.83 5.86 5.87 5.87 5.88 5.88 5.89 5.90 5.90 5.105 5.130 5.134 5.135 5.136 5.136 5.136 5.137 5.137 5.138 5.138 5.139 5.139 5.148 5.148 5.151 5.154

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MISCELLANY Table 5.27 Compressibility of Water Table 5.28 Mass of Water Vapor in Saturated Air Table 5.29 Van der Waals’ Constants for Gases Table 5.30 Triple Points of Various Materials 5.9.1 Some Physical Chemistry Equations for Gases

5.155 5.155 5.156 5.157 5.168 5.169

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5.1

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SOLUBILITIES

TABLE 5.1 Solubility of Gases in Water The column (or line entry) headed “␣” gives the volume of gas (in milliliters) measured at standard conditions (0⬚C and 760 mm or 101.325 kN · m⫺2) dissolved in 1 mL of water at the temperature stated (in degrees Celsius) and when the pressure of the gas without that of the water vapor is 760 mm. The line entry “A” indicates the same quantity except that the gas itself is at the uniform pressure of 760 mm when in equilibrium with water. The column headed “1” gives the volume of the gas (in milliliters) dissolved in 1 mL of water when the pressure of the gas plus that of the water vapor is 760 mm. The column headed “q” gives the weight of gas (in grams) dissolved in 100 g of water when the pressure of the gas plus that of the water vapor is 760 mm. Air*

Acetylene

Ammonia

Bromine

Temp. ⬚C

␣

q

␣(⫻103)

% oxygen in air

␣

q

␣

q

0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 35 40 45 50 60 70 80 90 100

1.73 1.68 1.63 1.58 1.53 1.49 1.45 1.41 1.37 1.34 1.31 1.27 1.24 1.21 1.18 1.15 1.13 1.10 1.08 1.05 1.03 1.01 0.99 0.97 0.95 0.93 0.91 0.89 0.87 0.85 0.84 — — — — — — — — —

0.200 0.194 0.188 0.182 0.176 0.171 0.167 0.162 0.157 0.154 0.150 0.146 0.142 0.138 0.135 0.131 0.129 0.125 0.123 0.119 0.117 0.115 0.112 0.110 0.107 0.105 0.102 0.100 0.098 0.095 0.094 — — — — — — — — —

29.18 28.42 27.69 26.99 26.32 25.68 25.06 24.47 23.90 23.36 22.84 22.34 21.87 21.41 20.97 20.55 20.14 19.75 19.38 19.02 18.68 18.34 18.01 17.69 17.38 17.08 16.79 16.50 16.21 15.92 15.64 — 14.18 — 12.97 12.16 — 11.26 — 11.05

34.91 34.87 34.82 34.78 34.74 34.69 34.65 34.60 34.56 34.52 34.47 34.43 34.38 34.34 34.30 34.25 34.21 34.17 34.12 34.08 34.03 33.99 33.95 33.90 33.86 33.82 33.77 33.73 33.68 33.64 33.60 — — — — — — — — —

1130 — — — 1047 — — — 947 — 870 — 857 837 — 770 775 — — — 680 — — — 639 — — — 586 — 530 — 400 — 290 200 — — — —

89.5 — — — 79.6 — — — 72.0 — 68.4 — 65.1 63.6 — — 58.7 — — — 52.9 — — — 48.2 — — — 44.0 — 41.0 — 31.6 — 23.5 16.8 11.1 6.5 3.0 0.0

60.5 — 54.1 — 48.3 — 43.3 — 38.9 — 35.1 — 31.5 — 28.4 — 25.7 — 23.4 — 21.3 — 19.4 — 17.7 — 16.3 — 15.0 — 13.8 — 9.4 — 6.5 4.9 3.8 3.0 — —

42.9 — 38.3 — 34.2 — 30.6 — 27.5 — 24.8 — 22.2 — 20.0 — 18.0 — 16.4 — 14.9 — 13.5 — 12.3 — 11.3 — 10.3 — 9.5 — 6.3 — 4.1 2.9 1.9 1.2 — —

* Free from NH3 and CO2 ; total pressure of air ⫹ water vapor is 760 mm.

short standard long

DEAN #37261 (McGHP)

TABLE 5.1 Solubility of Gases in Water (Continued)

Temp. ⬚C

Carbon dioxide

Carbon monoxide

␣

␣

q

q

Chlorine

Ethane

l

q

␣

Ethylene

␣

q

Hydrogen

␣

q

q

0.334 0.321 0.309 0.297 0.287

6 3 1 8 1

0.035 0.034 0.033 0.032 0.032

37 55 75 97 22

0.004 0.004 0.004 0.004 0.003

397 293 191 092 996

— — — — —

— — — — —

0.098 0.094 0.090 0.087 0.083

74 76 93 25 72

0.013 0.012 0.012 0.011 0.011

17 63 12 62 14

0.226 0.219 0.211 0.204 0.197

0.028 0.027 0.026 0.025 0.024

1 2 2 3 4

0.021 0.021 0.021 0.020 0.020

48 26 05 84 64

0.000 0.000 0.000 0.000 0.000

192 190 188 186 184

2 1 1 2 3

5 6 7 8 9

1.424 1.377 1.331 1.282 1.237

0.277 0.268 0.258 0.249 0.240

4 1 9 2 3

0.031 0.030 0.030 0.029 0.028

49 78 09 42 78

0.003 0.003 0.003 0.003 0.003

903 813 725 640 559

— — — — —

— — — — —

0.080 0.077 0.074 0.071 0.068

33 09 00 06 26

0.010 0.010 0.009 0.009 0.009

69 25 83 43 06

0.191 0.184 0.178 0.173 0.167

0.023 0.022 0.022 0.021 0.020

7 8 0 4 7

0.020 0.020 0.020 0.019 0.019

44 25 07 89 72

0.000 0.000 0.000 0.000 0.000

182 180 178 177 175

4 6 9 2 6

10 11 12 13 14

1.194 1.154 1.117 1.083 1.050

0.231 0.223 0.216 0.209 0.203

8 9 5 8 2

0.028 0.027 0.027 0.026 0.025

16 57 01 46 93

0.003 0.003 0.003 0.003 0.003

479 405 332 261 194

3.148 3.047 2.950 2.856 2.767

0.997 0.965 0.934 0.905 0.876

2 4 6 0 8

0.065 0.063 0.061 0.058 0.056

61 28 06 94 94

0.008 0.008 0.008 0.007 0.007

70 38 08 80 53

0.162 0.157 0.152 0.148 0.143

0.020 0.019 0.018 0.018 0.017

0 4 8 3 6

0.019 0.019 0.019 0.019 0.018

55 40 25 11 97

0.000 0.000 0.000 0.000 0.000

174 172 171 169 168

0 5 0 6 2

15 16 17 18 19

1.019 0.985 0.956 0.928 0.902

0.197 0.190 0.184 0.178 0.173

0 3 5 9 7

0.025 0.024 0.024 0.024 0.023

43 94 48 02 60

0.003 0.003 0.003 0.002 0.002

130 066 007 947 891

2.680 2.597 2.517 2.440 2.368

0.849 0.823 0.797 0.773 0.751

5 2 9 8 0

0.055 0.053 0.051 0.050 0.048

04 26 59 03 58

0.007 0.007 0.006 0.006 0.006

27 03 80 59 39

0.139 0.136 0.132 0.129 0.125

0.017 0.016 0.016 0.015 0.015

1 7 2 8 3

0.018 0.018 0.018 0.018 0.018

83 69 56 44 31

0.000 0.000 0.000 0.000 0.000

166 165 164 162 161

8 4 1 8 6

INTERACTIVE

1.713 1.646 1.584 1.527 1.473

LEFT

0 1 2 3 4

5.4

top of page

short standard

base of DF

TABLE 5.1 Solubility of Gases in Water (Continued) Carbon dioxide

Carbon monoxide

Temp. ⬚C

␣

␣

20 21 22 23 24

0.878 0.854 0.829 0.804 0.781

0.168 0.164 0.159 0.154 0.149

8 0 0 0 3

0.023 0.022 0.022 0.022 0.021

19 81 44 08 74

0.002 0.002 0.002 0.002 0.002

838 789 739 691 646

2.299 2.238 2.180 2.123 2.070

0.729 0.710 0.691 0.673 0.657

3 0 8 9 2

0.047 0.045 0.044 0.043 0.042

24 89 59 35 17

0.006 0.006 0.005 0.005 0.005

20 02 84 67 51

0.122 0.119 0.116 0.114 0.111

0.014 0.014 0.014 0.013 0.013

9 6 2 9 5

0.018 0.018 0.017 0.017 0.017

19 05 92 79 66

0.000 0.000 0.000 0.000 0.000

160 158 157 156 154

3 8 5 1 8

25 26 27 28 29

0.759 0.738 0.718 0.699 0.682

0.144 0.140 0.136 0.132 0.129

9 6 6 7 2

0.021 0.021 0.020 0.020 0.020

42 10 80 51 24

0.002 0.002 0.002 0.002 0.002

603 560 519 479 442

2.019 1.970 1.923 1.880 1.839

0.641 0.625 0.611 0.597 0.584

3 9 2 5 7

0.041 0.039 0.038 0.037 0.037

04 97 95 99 09

0.005 0.005 0.005 0.004 0.004

35 20 06 93 80

0.108 0.106 0.104 0.102 0.100

0.013 0.012 0.012 0.012 0.012

1 9 6 3 1

0.017 0.017 0.017 0.017 0.017

54 42 31 20 09

0.000 0.000 0.000 0.000 0.000

153 152 150 149 148

5 2 9 6 4

30 35 40 45 50

0.665 0.592 0.530 0.479 0.436

0.125 0.110 0.097 0.086 0.076

7 5 3 0 1

0.019 0.018 0.017 0.016 0.016

98 77 75 90 15

0.002 0.002 0.002 0.001 0.001

405 231 075 933 797

1.799 1.602 1.438 1.322 1.225

0.572 0.510 0.459 0.422 0.392

3 4 0 8 5

0.036 0.032 0.029 0.026 0.024

24 30 15 60 59

0.004 0.004 0.003 0.003 0.002

68 12 66 27 94

0.098 — — — —

0.011 8 — — — —

0.016 99 0.016 66 0.016 44 0.016 24 0.016 08

0.000 147 4 0.000 142 5 0.000 138 4 0.000 134 1 0.000 128 7

60 70 80 90 100

0.359 — — — —

0.057 6 — — — —

0.001 522 0.001 276 0.000 980 0.000 57 0.000 00

1.023 0.862 0.683 0.39 0.00

0.329 5 0.279 3 0.222 7 0.127 0.000

— — — — —

— — — — —

0.016 00 0.016 0 0.016 0 0.016 0 0.016 0

0.000 117 8 0.000 102 0.000 079 0.000 046 0.000 000

q

q

l

Ethane

␣

q

Ethylene

␣

q

0.002 39 0.001 85 0.001 34 0.000 8 0.000 0

␣

q

q

(McGHP)

0.021 77 0.019 48 0.018 26 0.017 6 0.017 2

Hydrogen

DEAN #37261

0.014 88 0.014 40 0.014 30 0.014 2 0.014 1

Chlorine

RIGHT

5.5

INTERACTIVE

top of page

short standard

base of DF

DEAN #37261 (McGHP)

TABLE 5.1 Solubility of Gases in Water (Continued) Hydrogen sulfide Temp. ⬚C

␣

Methane

␣

q

Nitric oxide

␣

q

Nitrogen*

␣

q

Oxygen

␣

q

Sulfur dioxide q

l

q

0.706 0.683 0.661 0.640 0.620

6 9 9 7 1

0.055 0.054 0.052 0.050 0.049

63 01 44 93 46

0.003 0.003 0.003 0.003 0.003

959 842 728 619 513

0.073 0.071 0.069 0.068 0.066

81 84 93 09 32

0.009 0.009 0.009 0.009 0.008

833 564 305 057 816

0.023 0.022 0.022 0.021 0.021

54 97 41 87 35

0.002 0.002 0.002 0.002 0.002

942 869 798 730 663

0.048 0.047 0.046 0.045 0.043

89 58 33 12 97

0.006 0.006 0.006 0.006 0.006

945 756 574 400 232

79.789 77.210 74.691 72.230 69.828

22.83 22.09 21.37 20.66 19.98

5 6 7 8 9

3.977 3.852 3.732 3.616 3.505

0.600 0.580 0.562 0.544 0.527

1 9 4 6 6

0.048 0.046 0.045 0.044 0.042

05 69 39 13 92

0.003 0.003 0.003 0.003 0.003

410 312 217 127 039

0.064 0.062 0.061 0.059 0.058

61 98 40 90 46

0.008 0.008 0.008 0.007 0.007

584 361 147 943 747

0.020 0.020 0.019 0.019 0.019

86 37 90 45 02

0.002 0.002 0.002 0.002 0.002

600 537 477 419 365

0.042 0.041 0.040 0.039 0.038

87 80 80 83 91

0.006 0.005 0.005 0.005 0.005

072 918 773 632 498

67.485 65.200 62.973 60.805 58.697

19.31 18.65 18.02 17.40 16.80

10 11 12 13 14

3.399 3.300 3.206 3.115 3.028

0.511 0.496 0.481 0.467 0.454

2 0 4 4 0

0.041 0.040 0.039 0.038 0.037

77 72 70 72 79

0.002 0.002 0.002 0.002 0.002

955 879 805 733 665

0.057 0.055 0.054 0.053 0.052

09 87 70 57 50

0.007 0.007 0.007 0.007 0.006

560 393 233 078 930

0.018 0.018 0.017 0.017 0.017

61 23 86 50 17

0.002 0.002 0.002 0.002 0.002

312 263 216 170 126

0.038 0.037 0.036 0.035 0.034

02 18 37 59 86

0.005 0.005 0.005 0.005 0.004

368 246 128 014 906

56.647 54.655 52.723 50.849 49.033

16.21 15.64 15.09 14.56 14.04

15 16 17 18 19

2.945 2.865 2.789 2.717 2.647

0.441 0.428 0.416 0.405 0.394

1 7 9 6 8

0.036 0.036 0.035 0.034 0.033

90 06 25 48 76

0.002 0.002 0.002 0.002 0.002

599 538 478 422 369

0.051 0.050 0.049 0.048 0.047

47 49 56 68 85

0.006 0.006 0.006 0.006 0.006

788 652 524 400 283

0.016 0.016 0.016 0.015 0.015

85 54 25 97 70

0.002 0.002 0.002 0.001 0.001

085 045 006 970 935

0.034 0.033 0.032 0.032 0.031

15 48 83 20 61

0.004 0.004 0.004 0.004 0.004

802 703 606 514 426

47.276 45.578 43.939 42.360 40.838

13.54 13.05 12.59 12.14 11.70

INTERACTIVE

4.670 4.522 4.379 4.241 4.107

LEFT

0 1 2 3 4

5.6

top of page

short standard

base of DF

TABLE 5.1 Solubility of Gases in Water (Continued) Hydrogen sulfide

Methane

Nitric oxide

Nitrogen*

Oxygen

Sulfur dioxide

20 21 22 23 24

2.582 2.517 2.456 2.396 2.338

0.384 0.374 0.364 0.355 0.346

6 5 8 4 3

0.033 0.032 0.031 0.031 0.030

08 43 80 19 61

0.002 0.002 0.002 0.002 0.002

319 270 222 177 133

0.047 0.046 0.045 0.044 0.043

06 25 45 69 95

0.006 0.006 0.005 0.005 0.005

173 059 947 838 733

0.015 0.015 0.014 0.014 0.014

45 22 98 75 54

0.001 0.001 0.001 0.001 0.001

901 869 838 809 780

0.031 0.030 0.029 0.029 0.028

02 44 88 34 81

0.004 0.004 0.004 0.004 0.004

25 26 27 28 29

2.282 2.229 2.177 2.128 2.081

0.337 0.329 0.320 0.313 0.305

5 0 8 0 5

0.030 0.029 0.029 0.028 0.028

06 52 01 52 06

0.002 0.002 0.002 0.001 0.001

091 050 011 974 938

0.043 0.042 0.041 0.041 0.040

23 54 88 24 63

0.005 0.005 0.005 0.005 0.005

630 530 435 342 252

0.014 0.014 0.013 0.013 0.013

34 13 94 76 58

0.001 0.001 0.001 0.001 0.001

751 724 698 672 647

0.028 0.027 0.027 0.026 0.026

31 83 36 91 49

30 35 40 45 50

2.037 1.831 1.660 1.516 1.392

0.298 0.264 0.236 0.211 0.188

3 8 1 0 3

0.027 0.025 0.023 0.022 0.021

62 46 69 38 34

0.001 0.001 0.001 0.001 0.001

904 733 586 466 359

0.040 0.037 0.035 0.033 0.031

04 34 07 11 52

0.005 0.004 0.004 0.004 0.003

165 757 394 059 758

0.013 0.012 0.011 0.011 0.010

42 56 84 30 88

0.001 0.001 0.001 0.001 0.001

624 501 391 300 216

0.026 0.024 0.023 0.021 0.020

08 40 06 87 90

60 70 80 90 100

1.190 1.022 0.917 0.84 0.81

0.148 0 0.110 1 0.076 5 0.041 0.000

␣

q

␣

q

0.019 54 0.018 25 0.017 70 0.017 35 0.017 0

0.001 144 0.000 926 0.000 695 0.000 40 0.000 00

␣

q

0.029 54 0.028 10 0.027 00 0.026 5 0.026 3

0.003 237 0.002 668 0.001 984 0.001 13 0.000 00

␣

q

0.010 23 0.009 77 0.009 58 0.009 5 0.009 5

0.001 052 0.000 851 0.000 660 0.000 38 0.000 00

q

0.019 46 0.018 33 0.017 61 0.017 2 0.017 0

l

q

339 252 169 087 007

39.374 37.970 36.617 35.302 34.026

11.28 10.88 10.50 10.12 9.76

0.003 0.003 0.003 0.003 0.003

931 857 787 718 651

32.786 31.584 30.422 29.314 28.210

9.41 9.06 8.73 8.42 8.10

0.003 0.003 0.003 0.002 0.002

588 315 082 858 657

27.161 22.489 18.766 — —

7.80 6.47 5.41 — —

— — — — —

— — —

0.002 274 0.001 856 0.001 381 0.000 79 0.000 00

(McGHP)

␣

DEAN #37261

Temp. ⬚C

—

* Atmospheric nitrogen containing 98.815% N2 by volume ⫹ 1.185% inert gases.

RIGHT

5.7

INTERACTIVE

top of page

short standard

base of DF

Substance

␣ A l ␣ ␣ A A g · L⫺1 ␣ ␣

10⬚

0.052 8 0.009 8 612 512 0.110 5

0.041 3 0.009 11 582 475 0.081 0 0.011 79 ⬚ 0.88 0.029 912 ⬚ 0.326 0.174

0.039 4 0.510 0.242

20⬚ 0.033 7 0.008 6 442 0.062 6 0.010 6 0.63 0.021 019 ⬚ 0.222 0.123

30⬚

40⬚

0.028 8 0.008 39 53325 ⬚ 412 0.051 1 0.010 0

0.025 1 0.008 41

0.013927 ⬚ 0.162 0.098

0.004 2 0.126 0.082

385 0.043 3 0.009 4842 ⬚

60⬚

80⬚

0.020 9 0.009 02 46950 ⬚ 339 0.035 7

0.018 4 0.009 4270 ⬚ 40675 ⬚ 0.009 8473 ⬚

0 0.085

(McGHP)

Argon Helium Hydrogen bromide Hydrogen chloride Krypton Neon Nitrous oxide Ozone Radon Xenon

0⬚

DEAN #37261

TABLE 5.1 Solubility of Gases in Water (Continued)

5.8

LEFT INTERACTIVE

top of page

short standard

base of DF

DEAN #37261

TABLE 5.2 Solubilities of Inorganic Compounds and Metal Salts of Organic Acids in Water at Various Temperatures Solubilities are expressed as the number of grams of substance of stated molecular formula which when dissolved in 100 g of water make a saturated solution at the temperature stated (⬚C). Substance

0⬚

NH4Al(SO4)2 NH4N3 NH4Br NH4Cl (NH4)2TrCl6 (NH4)2PtCl6 (NH4)2CrO4 (NH4)Cr(SO4)2 (NH4)2Co(SO4)2 (NH4)2Cr2O7 NH4H2AsO4 NH4H2PO4 (NH4)2S2O6 NH4CHO2 NH4HCO3 (NH4)2HPO4 NH4C4H5O6 NH4I (NH4)2Fe(SO4)2

2.10 16.0 60.5 29.4 0.56 0.289 25.0 3.95 6.0 18.2 33.7 22.7 133 102 11.9 42.9 1.00 155 12.5

44.9 0.56 66.7 128 33.5 4.60

45.8 0.67 73.9 133 36.4 6.39

5.00 68.1 33.2 0.71 0.374 29.2 9.5 25.5 29.5 151 16.1 62.9 1.88 163 17.2

7.74 25.3 76.4 37.2 0.95 0.499 34.0 13.0 35.6 48.7 37.4 166 143 21.7 68.9 2.70 172 26.4

30⬚

40⬚

46.6 0.78 81.8

47.3 0.91 88.7

40.4 9.37

45.8 14.39

59.2 35.35

10.9

14.9 37.1 91.2 45.8 1.56 0.815 45.3 32.6 22.0 58.5 63.8 56.7

26.7

83.2 41.4 1.20 0.637 39.3 18.8 17.0 46.5 46.4 179 28.4 75.1 182 33

60⬚

80⬚

48.1 1.1 106

48.6 1.32 132

90⬚

100⬚

73.0

80.8

49.0 1.72 160 182 89.0

108 55.3 2.45 1.44 59.0

125 65.6 4.38 2.16 76.1

135 71.2

145 77.3

33.5 86.0 83.0 82.5

49.0 115 107 118

58.0

204 36.6 81.8

311 59.2 97.2

533 109

191 46

209

229

153

2.61

3.36

75.1 156

122 173

170

354

INTERACTIVE

43.9 0.56 60.0 122 31.2 3.15

20⬚

RIGHT

AlCl3 AlF3 Al(NO3)3 Al(ClO4)3 Al2(SO4)3 Al2Tl2(SO4)4

10⬚

(McGHP)

Aluminum chloride fluoride nitrate perchlorate sulfate thallium(l) sulfate Ammonium aluminum sulfate azide bromide chloride chloroiridate(IV) chloroplatinate(IV) chromate chromium(III) sulfate cobalt(II) sulfate dichromate dihydrogen arsenate dihydrogen phosphate dithionate formate hydrogen carbonate hydrogen phosphate hydrogen tartrate iodide iron(II) sulfate

Formula

250

5.9

top of page

short standard

base of DF

DEAN #37261

TABLE 5.2 Solubilities of Inorganic Compounds and Metal Salts of Organic Acids in Water at Various Temperatures (Continued) Substance

10⬚

20⬚

18.0 6.50 192 4.45 21.7 115 75.4 60.8 63.0 91.2 170 0.48 12.5 910

(NH4)2Mg(SO4)2 (NH4)2Ni(SO4)2 NH4NO3 (NH4)2C2O4 NH4ClO4 (NH4)2SeO3 (NH4)2SO4 (NH4)2SO3 (NH4)2C4H4O6 (NH4)3SbS4 NH4SCN NH4VO3 (NH4)2Zn(SO4)2 SbCl3

11.8 1.00 118 2.2 12.0 96 70.6 47.9 45.0 71.2 120

14.6 4.00 150 3.21 16.4 105 73.0 54.0 55.0

7.0 602

9.5

SbF3

385 42 59.5 1.20 58.8 12.5 0.29 98 37.0 11.71 20.3 31.2 43.9

444 30 62.1 1.49 62 16.1 0.44 101 36.1 8.38 26.9 33.5 44.6 0.159

28 65.8 1.82 72 17.417⬚ 0.65 104 35.4 6.89 33.9 35.8 45.4 0.160

21.7 9.20 242 6.09 27.7 126 78.0 68.8 70.5 120 208 0.84 16.0 1087

40⬚

25.8 12.0 297 8.18 34.6 143 81 78.4 76.5 234 1.32 20.0 1368

60⬚

80⬚

35.1 17.0 421 14.0 49.9 192 88 104 86.9

48.3 580 22.4 68.9 95 144

90⬚

100⬚

65.7 740 27.9

871 34.7

150

103 153

346 2.42 30.0 46.6 58.0 [completely miscible at 72⬚]

72.4

562

69.8 2.31 75

71.2 2.93 78.5

73.0 4.31 75.0

75.1 6.11 74.0

0.95 109 34.9 5.87 41.6 38.1

1.31 114 35.2 5.79 49.7 40.8 47.9

2.27 123 37.2 8.39 66.7 46.2 53.8

3.52 135 41.7 14.71 84.8 52.5 66.6

76.7 8.2 74.8 4.26 45.5 19.28 55.8

5.39 149 48.195⬚

INTERACTIVE

AsH3 As2O5 As2O3 Ba(C2H3O2)2 · 3H2O Ba(N3)2 Ba(BrO3)2 · H2O BaBr2 · 2H2O Ba(C4H7O2)2 Ba(C6H11O2)2 · 3.5H2O Ba(ClO3)2 · H2O BaCl2 · 2H2O Ba(ClO2)2 BaF2

144

30⬚

LEFT

fluoride Arsenic hydride (760 mm), cc oxide (pent-) oxide (tri-) Barium acetate azide bromate bromide n-butyrate caproate chlorate chloride chlorite fluoride

0⬚

(McGHP)

Ammonium magnesium sulfate nickel sulfate nitrate oxalate perchlorate selenite sulfate sulfite tartrate thioantimonate(V) thiocyanate vanadate zinc sulfate Antimony(III) chloride

Formula

105 59.4 80.8

0.162

5.10

top of page

short standard

base of DF

26.2 1.67

28.0 2.48

182 4.95 50.3 239 57.2 0.421 18.3 2.88 0.021 97 37.0 2.67 56.3 299 90

201 6.67 60

8.3 78.7 122

0.182

57.5 0.393 32.5 10.38 0.032 113 41.4 6.72 129 348 132 135 18.6 87.9 167 195 58.9 33.8 3.02 18534⬚ 17.25 71 100 1.83 16.1

0.160

34.0 8.22 0.057

38.6 20.94

14.1 102 416 59.0 0.366 38.5 14.89 0.035 125 45.8 8.72 152 376

264 20.4 151 495 62.0 0.306 49.6 27.69 0.044 178 53.1 14.81 153 455

135 25.3 92.1 194 203 55.0 78.5 33.2 3.42 213 16.40

136 59.5 100 310 221 44.2 81.8 32.7 4.71 278 15.15

128 1.49

137 0.83

17.05 5.29 17.05 0.141

17.50 17.50 0.121

44.2 101.4

47.6

291 27.2 222 575 67.8 0.237 61.5 49.91 0.053 67.2 23.62 156

140 80.5 111 713 243 32.5 66.7 33.5 6.87 295 14.95 147

17.95 12.11 17.95

261 73.0

67.34

51.3

301 34.4 325 653 82.7 73.5 60.29

30.38

82.8 40.25 160

85.2

147 94.6 125

27.2 63.1 31.1 8.55

154

36.80 0.086

272 22.0 60.8 29.7 8.70 312105⬚ 15.85 159

INTERACTIVE

16.15 0.189

136 180 68.4 76.0 36.0 2.45 132 19.15 52 64.7

0.418 26.8 7.86 0.028 108 39.1 5.04 98.8 322 113 135 14.4 84.7 150 188 64.0 76.6 34.7 2.72 143 18.20 59 74.5 2.25 16.6 16.60 3.72 16.60 0.173

31.9 5.59 0.046 250 11.48

RIGHT

72.5 75.4 37.4 2.32 125 20.31 48 59.5 4.5 17.3 16.15

56.8 0.432 22.3 4.89 0.024 102 37.6 3.73 75.4 308 100 135 11.1

29.9 3.89 0.035 223 9.02 72.8 336

(McGHP)

formate iodide nitrate perchlorate selenate sulfate Calcium acetate benzoate bromide butyrate cacodylate chloride chromate (mn) formate gluconate hydrogen carbonate hydroxide

Ba(CHO2)2 Ba(OH)2 Ba(IO3)2 BaI2 · 2H2O Ba(NO3)2 Ba(NO2)2 · H2O Ba(ClO4)2 · 3H2O Ba(C3H5O2)2 · H2O BaC4H4O4 Ba(SO3NH2)2 BaS Ba(C2H2O3)2 Be(NO3)2 BeSO4 H3BO3 CdBr2 Cd(ClO3)2 CdCl2 · 2.5H2O CdCl2 · H2O Cd(CHO2)2 CdI2 Cd(NO3)2 Cd(ClO4)2 · 6H2O CdSeO4 CdSO4 Ca(OAc)2 · 2H2O Ca(OBz)2 · 3H2O CaBr2 · 6H2O Ca(C4H7O2)2 Ca(C2H6AsO2)2 · 9H2O CaCl2 · 6H2O CaCrO4 CaCrO4 · 2H2O Ca(CHO2)2 Ca(C6H11O7)2 · H2O Ca(HCO3)2 Ca(OH)2

DEAN #37261

formate hydroxide iodate iodide nitrate nitrite perchlorate propionate isosuccinate sulfamate sulfide tartrate Beryllium nitrate sulfate Boric acid Cadmium bromide chlorate chloride

18.40 57.296⬚ 18.40 0.076

5.11

top of page

short standard

base of DF

DEAN #37261

TABLE 5.2 Solubilities of Inorganic Compounds and Metal Salts of Organic Acids in Water at Various Temperatures (Continued)

Calcium iodate iodide lactate levulinate malonate nitrate nitrite propionate selenate succinate sulfamate sulfate

Ca(IO3)2 · 6H2O CaI2 Ca(C3H5O3)2 · 5H2O Ca(C10H14O6) · 2H2O Ca(C3H2O4) Ca(NO3)2 · 4H2O Ca(NO2)2 · 4H2O Ca(C3H5O2)2 · H2O CaSeO4 · 2H2O Ca(C3H2O2)2 · 3H2O Ca(SO3NH2)2 CaSO4 · 1⁄2 H2O CaSO4 · 2H2O CaC4H4O6 · 4H2O Ca2UO2(CO3)3 · 10H2O Ca(C5H9O2)2 Ca(C5H9O2)2 · 3H2O CS2 COS

0⬚ 0.090 64.6 3.1 38.1 0.29 102 63.9 42.80 9.73 1.127 56.5

10⬚

66.0

0.33 115

9.77 1.22 62.8

0.223 0.026 0.1 9.82 26.05 0.204

9.25 22.70 0.194

133.3

83.6

CF4

0.244 0.029

0.595 242

Ce(NH4)2(NO3)6 Ce(NH4)(SO4)2 Ce2(SeO3)3

39.5

37.2

30⬚

40⬚

60⬚

80⬚

90⬚

0.24 67.6 5.415⬚ 45.116⬚ 0.36 129 84.518⬚ 39.85 9.22 1.28 72.3 0.32 0.25518⬚ 0.034 0.423 8.80 21.80 0.179

0.38 69.0 7.9 55.0 0.40 152 104

0.52 70.8

0.65 74

0.66 78

0.67

70.345⬚ 0.42 191

88.755⬚ 0.46

56.1 0.490

8.79 84.5 0.2925⬚ 0.264 0.046 8.40 21.68 0.155

134 38.25 7.14 1.18 100.1 0.2635⬚ 0.265 0.063 0.8 8.05 22.00 0.111

0.89 150.0 0.2145⬚ 0.24465⬚ 0.091 1.555⬚ 7.78 18.38

0.68 215.2 0.14565⬚ 0.23475⬚ 0.130

81

166 42.15

363 178 48.44 0.66

24295⬚ 0.1275⬚

7.95 16.88

8.20 16.65

1.33 4.6

2.1

0.071 0.205

8.78 16.55

40.3 0.415

0.366

276

318

376

681

135

150

169

213

5.53 35.2

0.48 358 151 39.85

100⬚

4.49 33.2

3.48 32.6

2.02 13.7

INTERACTIVE

Ce(NH4)2(NO3)5

20⬚

LEFT

tartrate uranyl carbonate valerate isovalerate Carbon disulfide oxide sulfide (STP) mL/100 mL tetrafluoride (STP) mL/100 g Cerium(III) ammonium nitrate (IV) ammonium nitrate (III) ammonium sulfate (III) selenate

Formula

(McGHP)

Substance

5.12

top of page

short standard

base of DF

18.8 0.21 2.46 161 0.0047 335 44.1 9.33 0.8 167 2.76 1085⬚ 164.8 104 91.9 135 43.5

50.2 3.98

3.8 175 0.5 0.0064 381 58.5 14.9 1.0 173 6.00 12415⬚ 123 162 47.7 89.6 0.24 30.5 56.3 32.012⬚ 15.1 116 70.9 76.5 100 7.2 14.53 27.5 0.02015⬚ 70.1 3.30

7.24 7.10 0.61 4.53 9.5 197 1.7 0.0119 533 96 33.9 2.6 184

5.63 5.70 0.85 5.3035⬚ 13.8 208 3.3 0.0158 694 12445⬚ 47.2 4.0 190

3.87 4.04 2.00

5.40

26.2 230 8.9 0.0290

45.0 250 19.5 0.0525

58.0 260 27.7 0.0675

79.0 271 37.9 0.0914

150 83.8 7.3 200

190 134 14.4 210

205 163 20.5 215

197 30.0 220

172.5

183.9

191.6

206.8

163 214 69.5 0.88 125 0.85 48.8 88.1 43.8 30.5 13150⬚ 87.6 91.250⬚ 163 18.2 25.22 44.6 0.142 166

227 316 93.8 0.82 174

241

257

10.5

22.7

15235⬚

128 195 59.7 0.90 111 0.61 42.0 73.0 38.3 24.4 128 77.3 84.125⬚ 156 13.6 21.04 37.8 0.089 126 2.32

55.0 101 56.6 46.3 96.5 182 36.50 61.8 0.197

97.6 0.73 204

101 300

53.8

45.3

76.5 69.7

76.5 86.1

104 93.275⬚ 208 53.68 83.8 0.144

106 0.70

38.9

107

108

120

222

247

INTERACTIVE

84.0 0.076 25.5 44.8 28.2 11.5 107 68.6 73.5 83.5 5.1 12.04 23.1

0.30

9.84 9.43 0.40 3.6625⬚ 6.2 187 0.8 0.0087 450 76.5 23.0 1.6 179 8.7015⬚ 13025⬚ 167.2 130 112 180 52.9 1.02 97.4 0.40 36.1 65.4 35.0 19.4 126 73.0 81.6 125 10.0 17.51 32.0 0.042 95.6 2.60

RIGHT

Copper(II) ammonium chloride ammonium sulfate bromide chloride fluorosilicate nitrate potassium sulfate selenate sulfate tartrate Gadolinium bromate sulfate

21.4

(McGHP)

Cesium aluminum sulfate bromate chlorate chloride chloroaurate(III) chloroplatinate(IV) formate iodide nitrate perchlorate sulfate Chlorine dioxide Chromium(III) nitrate (VI) oxide (III) perchlorate Cobalt(II) bromide chlorate chloride iodate nitrate nitrite sulfate

Ce2(SO4)3 · 9H2O Ce2(SO4)3 · 8H2O Cs2Al2(SO4)4 CsBrO3 CsClO3 CsCl CsAuCl4 Cs2PtCl6 CsCHO2 CsI CsNO3 CsClO4 Cs2SO4 ClO2 Cr(NO3)3 CrO3 Cr(ClO4)3 CoBr2 Co(ClO3)2 CoCl2 Co(IO3)2 Co(NO3)2 Co(NO2)2 CoSO4 CoSO4 · 7H2O CuCl2 · 2NH4Cl CuSO4 · (NH4)2SO4 CuBr2 CuCl2 CuSiF6 Cu(NO3)2 CuSO4 · K2SO4 CuSeO4 CuSO4 · 5H2O CuC4H4O6 · 3H2O Gd(BrO3)3 · 9H2O Gd2(SO4)3

DEAN #37261

(III) sulfate

114

5.13

top of page

short standard

base of DF

DEAN #37261

TABLE 5.2 Solubilities of Inorganic Compounds and Metal Salts of Organic Acids in Water at Various Temperatures (Continued)

GeO2 Ho2(SO4)3 · 8H2O N2H5NO3 N2H6SO4 (N2H5)2SO4 HBr HCl H2Se I2 (NH4)2IrCl6 Na2IrCl6

0⬚

10⬚

20⬚

0.49

0.43 8.18 266 2.87

175

210.3 77.2 351 0.020 0.706 34.4615⬚

204.015⬚ 72.1 289 0.029 0.77

FeSO4 · (NH4)2SO4 · 6H2O FeBr2 FeCl2 FeCl3 · 6H2O

17.23 101 49.7 74.4

31.0 109 59.0

36.47 117 62.5 91.8

FeSiF6 · 6H2O Fe(NO3)2 · 6H2O Fe(NO3)3 · 9H2O Fe(ClO4)3 FeSO4 · 7H2O La(BrO3)3 La(NO3)3 La2(SeO3)3 La2(SO4)3 Pb(C2H3O2)2 PbBr2 PbCl2 PbSiF6

72.1 113 112.0 289 28.8 98 100 50.5 3.00 19.8 0.45 0.67 190

74.4 134

40.0 120 45 2.72 29.5 0.63 0.82

40⬚

0.50 6.7125⬚ 402 3.89 221

0.61 4.52 607 4.15 300 171.550⬚ 63.3

67.3 0.039 1.21 56.17 45.0 124 66.7 106.8

0.052 1.57 96.00

133 70.0

77.025⬚ 137.7 368 48.0 149 136 45 2.33 44.3 0.86 1.00 222

422 60.0 200 45 1.90 69.8 1.12 1.20

60⬚

80⬚

2127 9.08 554

14.39 150.575⬚

168 45 1.67 116 1.50 1.42

100⬚

130.0

56.1 0.100 2.46 191.2

0.225 4.38 279.3

144 78.3

168 88.7

83.750⬚ 266 175.0 478 73.3

90⬚

772 100.7

0.315 dec

176 92.3

88.175⬚

79.9

0.445

184 94.9

100.1106⬚

68.3

247 18.5 1.26

5.4 0.91

2.2 0.79

2.29 1.94 403

3.23 2.54 428

3.86 2.88

57.8

INTERACTIVE

221.2 82.3 386 0.014 0.556

30⬚

LEFT

Germanium(IV) oxide Holmium sulfate Hydrazinium (1⫹) nitrate (2⫹) sulfate (1⫹) sulfate Hydrogen bromide chloride selenide, mL at STP Iodine Iridium(IV) ammonium chloride sodium chloride Iron(II) ammonium sulfate (II) bromide (II) chloride (III) chloride (II) fluorosilicate (II) nitrate (III) nitrate (III) perchlorate (II) sulfate Lanthanum bromate nitrate selenate sulfate Lead(II) acetate bromide chloride fluorosilicate

Formula

(McGHP)

Substance

0.68 4.55 3.20 463

5.14

top of page

short standard

base of DF

0.044 37.5 31.2 61.3 38.9 0.90 154 143 1.54 241 69.2 105 32.3 9.97 11.91 151 82.6 53.4 70.9 42.7 0.101 25.0 36.1 42.0

12.11 157 60.8 82.5 49.0 23.3 35.5 31.8

59.7 99 123 53.6 14.2 7.2

67.2 44.7 2.7 179 160 1.33 372 83.5 136 141 39.3 12.35 165 79.5 70.1 96.8 56.1 0.05825⬚ 21.5 34.8 27.1 114 4.82 53.4 101 135 54.6 30.8 14.4 8.6 140

0.090 63.4 50.6 55.9 71.2 53.8 5.7 198 183 1.26 488 86.2 167 153 44.1 7.61 12.70 171 79.4 138 114 63.6 19.6 34.2 26.6 131 6.28 68.6 104 155 55.8 14.9 10.0

0.124 72.1 68.6 56.1 75.4 10.9 221 211 1.17 604 89.8 206 160 49.5 7.11 13.22 179 78.0 152 133 72.3 0.048 17.9 33.7 27.2 153 4.38 75.7 106 178 57.5 34.9 15.9 11.7 173

0.193 91.6

0.294 111

0.42 133

56.5 86.6

269 223 1.01 777 98.4 324 178 64.7 6.03 14.63 202 175 177 92.3 14.7 32.6 29.5 2.67 118 112 242 61.0 44.4 17.9 15.2

100

308 245 0.85

329

355 266 0.72

112 599 216 92.7

121

128

239 116

16.56 435

440

233 128

272 151

11.9 31.4

11.1 30.9

66.1

268 69.5

138 4.43 19.12 481 73.9 324

9.9

125

20.5 15.5 186

22.2 15.6

73.3

INTERACTIVE

120

35.7

0.069 54.3 40.8

RIGHT

2.50 56.7 98 114 52.9 26.3 14.0

0.056 46.2 35.1 55.2 64.2 41.6 1.3 166 147 1.43 283 74.5 113

(McGHP)

PbI2 Pb(NO3)2 LiC2H3O2 LiNH4SO4 LiN3 LiC7H5O2 LiBO2 LiBrO3 LiBr Li2CO3 LiClO3 LiCl LiAuCl4 Li2Pt(CN)4 LiCHO2 Li2HPO3 LiOH LiI Li2MoO4 LiNO3 LiNO2 LiClO4 LiPO3 Li2SeO3 Li2SO4 Li2C4H4O6 LiSCN Li3VO4 Mg(C2H3O2)2 MgBr2 Mg(ClO3)2 MgCl2 MgSiF6 Mg(CHO2)2 Mg(IO3)2 MgI2

DEAN #37261

iodide nitrate Lithium acetate ammonium sulfate azide benzoate borate (meta-) bromate bromide carbonate chlorate chloride chloroaurate(III) cyanoplatinate(II) formate hydrogen phosphite hydroxide iodide molybdate nitrate nitrite perchlorate phosphate (meta-) selenite sulfate tartrate (d-) thiocyanate vanadate Magnesium acetate bromide chlorate chloride fluorosilicate formate iodate iodide

23.9

5.15

top of page

short standard

base of DF

DEAN #37261

TABLE 5.2 Solubilities of Inorganic Compounds and Metal Salts of Organic Acids in Water at Various Temperatures (Continued) 10⬚

62.1 20.0 22.0 0.339 0.54 127 63.4

66.0 30.4 28.2 0.446 0.78 136 68.1

102 0.020 52.9 0.30 3.63 282

118 0.024 59.7 0.40 4.82 325

43.9

59.2 96.7 133 44.6 9.7 122 120 56.3 2.55

127 46.2 13.0 113 111 53.4

0.74 124 79.2 105

135 107

20⬚ 69.5 38.3 33.7 0.573 1.06 147 73.9 1.06 139 0.028 62.9 0.56 6.57 367 0.134 75.6 98.0 142 41.8 7.1 131 133 60.8 2.56 1.09 148 94.2 110

30⬚

40⬚

60⬚

73.6 44.3 38.9 0.751

78.9 48.6 44.5 0.959 1.02 169 88.5 0.67

78.9 55.8 54.6 0.779

157 80.8 206 0.033 62.9 0.66 8.34 407 0.285 95.2 99.6 145 39.9 5.3 138 155 70.6 1.15 1.43 161 105 113

60.0 0.91 10.2 455 0.454 116 102 159 39.9 4.1 144 181 73.2

174 119 117

80⬚ 91.6 55.8 0.642

90⬚

100⬚

106 52.9 0.622

197 109 0.44

225 113

226 114

53.6 1.68 16.3 499 1.08

45.6 2.77 30.0 541 1.74

40.9

105 211 43.9 2.8 153 221 81.2 2.56 1.06

7.0 2.2 154 308 86.6

3.3 1.2

184 158

187 187

50.4

228 115 0.48

35.3 4.9 61.3 580

155 87.6

INTERACTIVE

iodide nitrate perchlorate

Mg(NO3)2 MgSeO4 MgSO4 MgSO3 MgC4H4O6 MnBr2 MnCl2 MnF 2 Mn(NO3)2 MnC2O4 MnSO4 HgBr2 HgCl2 Hg2(ClO4)2 MoO3 Nd(BrO3)3 NdCl3 Nd(NO3)3 Nd2(SeO3)3 Nd2(SO4)3 NiBr2 Ni(ClO3)2 NiCl2 NiF2 Ni(IO3)2 Ni(IO3)2 · 4H2O NiI2 Ni(NO3)2 Ni(ClO4)2

0⬚

LEFT

Magnesium nitrate selenate sulfate sulfite tartrate Manganese bromide chloride fluoride nitrate oxalate sulfate Mercury(II) bromide (II) chloride (I) perchlorate Molybdenum trioxide Neodymium bromate chloride nitrate selenate sulfate Nickel bromide chlorate chloride fluoride iodate

Formula

(McGHP)

Substance

2.59 1.00 188 188

5.16

top of page

short standard

base of DF

3.09 53.6 116 26.6 105 3.3 28.0 0.48 56.3

22.5

43.6

47.6

44.4 37.7 6.43 9.52 256 5.90 50.8 70.7 6.91 65.3 150 38.9 111 7.3 34.2 61.8 0.78 63.7 172 15.5 10.0 33.9 12.3 22.6 6.6 46 28.2 94.9 0.50 0.151 1.28 337 33.7

46.6 43.4

49.2 50.4

55.6

64.5

14.23 283 8.39 55.8 76.7 9.64 70.7 170 45.6 114 10.1 37.2 94.9 1.00 66.7 194 19.3 13.6 52.0 18.1 28.0 9.3 53 35.1 108 0.66 0.202

21.52 324 11.7 61.0 82.1 13.1 75.4 191 53.1 117 13.9 40.1 145 1.36 67.8

44.32 350 24.8

84.5 381 71.0

22.7 85.5 233 67.5 127 23.8 45.8 405 2.45 70.1

34.1 94.9 276 83.5 140 37.6 51.3

23.3 18.2 78.3 26.3 33.5

32.5

47.7

139 45.6 50.2

177 73.0 70.4

59.3 41.4 138 0.96 0.253

70 54.8 142

66.9 150

361 39.9

398 47.5

471 65.6

70.1

76.7

120 398 109 106

99.2 298 148 46.0 53.9

3.71

49.9 104 325 101 156 56.3 56.3 5.03

74.5

580

194 83.5

71.5

91 74.2

INTERACTIVE

8.5 5.1 11.6 4.7 14.8 2.6 30.2 14.3 44.7 0.25 0.077 0.55

32.4 5.75 6.08 233 3.99 46.2 65.8 4.72 59.5 133 32.3 108 5.2 31.2 38.3 0.60 60.0 153 11.7 7.2 19.8 7.0 18.3 4.2 38 21.1 53.5 0.36 0.102 0.91 313 27.4

40.1

RIGHT

Osmium tetroxide Oxalic acid Potassium acetate aluminum sulfate azide benzoate bromate bromide cadmium bromide cadmium chloride carbonate chlorate chloride chloroaurate(III) chloroplatinate(IV) chromate citrate cobalt(II) sulfate copper(II) sulfate cyanoplatinate(II) dichromate dihydrogen phosphate dithionate ferricyanide ferrocyanide fluoride fluorogermanate(IV) fluorosilicate fluorotitanate(IV) formate hydrogen carbonate

NiSO4 · 7H2O OsO4 H2C2O4 KC2H3O2 KAl(SO4)2 KN3 KC7H5O2 KBrO3 KBr KCdBr3 KCdCl3 K2CO3 KClO3 KCl KAuCl4 K2PtCl6 K2CrO4 K3C6H5O7 K2Co(SO4)2 K2Cu(SO4)2 K2Pt(CN)4 K2Cr2O7 KH2PO4 K2S2O6 K3Fe(CN)6 K4Fe(CN)6 KF K2GeF6 K2SiF6 K2TiF6 KCHO2 KHCO3

(pale blue) (green) 26.2 5.26 3.54 216 3.00 41.4

(McGHP)

NiSO4 · 6H2O

DEAN #37261

Nickel sulfate

658

5.17

top of page

short standard

base of DF

DEAN #37261

TABLE 5.2 Solubilities of Inorganic Compounds and Metal Salts of Organic Acids in Water at Various Temperatures (Continued)

KHF2

24.5 115 36.2 0.231 95.7 4.60 128 19.6 14.0 3.37 13.9 279 25.5 0.76 0.17 2.83 1.65 0.34 21.2 107 169 7.4 106 8.8 306 177 96 13.0

10⬚ 30.1 162 0.358 103 6.27 136 24.5 19.5 4.50 21.2 292 31.9 1.06 0.28 4.31 2.67 0.63 81.5 32.4 109 186 9.3

320 198 18.9

20⬚

30⬚

40⬚

60⬚

39.2

46.8

56.5

78.8

114

215 48.6 0.523 112 8.08 144 32.1 25.0 5.94 31.6 306 36.4 1.68 0.42 6.34 4.70 0.99 92.3 47.1 111 203 11.1 106 27.5

300 54.3 0.762 126 10.3 153 39.1 30.4 7.72 45.3 320 39.9 2.56 0.65 9.03 7.75 1.47 108 61.3 113 217 13.0 107 50.4 302 255 175 35.0

408 61.0

900 76.4

96.1

122

134 12.6 162 44.9 36.6 9.85 61.3 329 43.8 3.73 1.0 12.6 11.0 2.2 133 78.6 115 217 14.8 107

154 18.3 176 57.2 50.2 15.4 106 348 53.2 7.3 2.1 22.1

24.8 192

178 32.3 206

116 119 220 18.2 108

315 289 205 44.9

372 238 72.1

224 155 25.9

4.58

80⬚

63.4 23.0 167 376 63.6 13.4 4.4

90⬚

198

27.8 203 390 69.2 17.7 5.9

100⬚

33.4 245 410 75.3 22.3

8.7 156 121 21.4

381 492 293

22.9

571 312

122 217 24.1 112

INTERACTIVE

KH3(SeO3)2 KHSO4 KC4H5O6 KOH KIO3 KI K2Fe(SO4)2 K2Mg(SO4)2 K2Ni(SO4)2 KNO3 KNO2 K2C2O4 KClO4 KIO4 KMnO4 K2S2O8 KReO4 K3PO4 KC7H5O3 K2SeO4 K2SeO3 K2SO4 K2SO3 K2TeO4 K3SbS4 KSCN K2S2O3 K2Zn(SO4)2 · 6H2O

0⬚

LEFT

Potassium hydrogen fluoride hydrogen selenite hydrogen sulfate hydrogen tartrate hydroxide iodate iodide iron(II) sulfate magnesium sulfate nickel sulfate nitrate nitrite oxalate perchlorate periodate permanganate peroxodisulfate perrhenate phosphate salicylate selenate selenite sulfate sulfite tellurate thioantimonate(V) thiocyanate thiosulfate zinc sulfate

Formula

(McGHP)

Substance

675

5.18

top of page

short standard

base of DF

Pr(BrO3)3 Pr(NO3)3 Pr2(SeO3)3 Pr2(SO4)3

91.8 112

36.2 19.8

15.6

12.6

0.72 90 2.1 77 0.014 62.0 5.10

19.5 1.09 37.5 34.2 426 90.1 0.73

1.50

99 3.4 84 4.8 0.020 67.5 7.47

108 5.4 91 9.9 0.028 73.6 10.8 5.9 5.8 554 20 52.9 1.55 212 48.1 62.5 93.4 567 166.7 257 1.05 0.16 15.3 172 216 0.34 525 7.53 0.80

443 8.0 33.0 1.19 187 42.6 47.6 92.4 122.2 222 0.89 0.11 10.4 120 167 0.22 484 4.82 0.70

144 178 31.2 2.56

2.20 3.6 119 8.0 98 15.5 0.040 78.9 14.5 10.0 9.5 614 35 81.2 2.20 238 53.6 79.0 94.6 1328 235.6 291 1.23 0.23 20.9 190 265 0.51 594 10.3 0.89

3.25 5.1 132 11.6 104 21.5 0.056 85.6 18.2 15.2 14.8 694 52 117 3.26 268 58.5 98.5 96.9 344.4 335 1.43 0.32 26.8 203 311 0.73 635 15.3 0.98

30.4 5.04

3.6 1.1

0.91

38 127 54.6 0.182

49 133 65.8 0.247

63 143 79.2 0.333

44.9

55.0

70.1

200 6.27 324 67.5

310 11.0

374 15.5

452 22.0

75.1

78.6

81.8

383.1 440 1.93 0.57

383.1

385.4

440 1.39

585

7.40 158 22 115 36.2 0.090 95.7 30.2 32.3 32.4 900

5.43 3.5 21.6

2.59 0.94

1.33

652

733

INTERACTIVE

85.9 122 0.16 455 2.30 0.57

1.05

114 162 32.4 9.89

RIGHT

RbCHO2 RbFe(SO4)2 · 12H2O RbNO3 RbClO4 RbC7H5O3 Rb2SO4 Sm(BrO3)3 SmCl3 H2SeO4 H2SeO3 SeO2 AgC2H3O2 AgBrO3 AgClO3 AgF AgNO3 AgNO2 AgClO4 AgNH2SO3 Ag2SO4

73.0

(McGHP)

Rb2Al2(SO4)4 RbBrO3 RbBr RbClO3 RbCl RbAuCl4 Rb2PtCl6 Rb2CrO4 Rb2Co(SO4)2 Rb2Cr2O7

55.9

DEAN #37261

Praseodymium bromate nitrate selenate sulfate Rubidium aluminum sulfate bromate bromide chlorate chloride chloroaurate(III) chloroplatinate(IV) chromate cobalt sulfate dichromate (mn) (tric) formate iron(III) sulfate nitrate perchlorate salicylate sulfate Samarium bromate chloride Selenic acid Selenious acid Selenium dioxide Silver acetate bromate chlorate fluoride nitrate nitrite perchlorate sulfamate sulfate

793 28.5 1.15

1.30

1.36

1.41

5.19

top of page

short standard

base of DF

DEAN #37261

TABLE 5.2 Solubilities of Inorganic Compounds and Metal Salts of Organic Acids in Water at Various Temperatures (Continued)

NaC2H3O2 Na2Al2(SO4)4 NaN3 NaC7H5O2 Na2B10O16 Na2B4O7 NaBrO3 NaBr Na2CO3 NaClO3 NaCl NaAuCl4 Na2IrCl6 Na2CrO4 NaCN Na2Cr2O7 NaC8H11N2O3 NaH2PO4

36.2 37.4 38.9 62.6 6.4 1.11 24.2 80.2 7.00 79.6 35.7

31.7 40.8 163

56.5 4.47 6.3

10.6 11.2 3.66 1.33 1.52 4.35

10⬚

20⬚

30⬚

40⬚

40.8 39.3 39.9 62.8 8.6 1.60 30.3 85.2 12.5 87.6 35.8 139 31.6 50.1 48.1 172 12.7

46.4 39.7 40.8 62.8 12.0 2.56 36.4 90.8 21.5 95.9 35.9 151 39.3 84.0 58.7 183 21.5

54.6 41.7

65.6 43.8

62.9 16.4 3.86 42.6 98.4 39.7 105 36.1 178 56.2 88.0 71.2 198 24.7

69.8

86.9

107

6.95 11.1

12.0 15.1 0.13

14.8

1.68 5.7

11.1 18.8 4.06 1.44 7.2

17.1 19.6 0.25 4.58 12.8 23.8 4.22 2.25 8.6

60⬚

80⬚

90⬚

139

153

63.1 22.0 6.67 48.8 107 49.0 115 36.4 227 96.1 96.0

64.5 37.9 19.0 62.6 118 46.0 137 37.1 900 192 115

68.6 63.4 31.4 75.7 120 43.9 167 38.0 279 125

215

269

376

405 48.0

133

172

211

234

18.4 24.7 6.54 22.7 14.2 29.9 4.40 1.92 2.83 10.3

36.1

49.3

105 17.0 43.7 4.68 2.24

170 22.2 62.1 4.89 2.62 3.36 18.7

14.3

161

70.6 83.5 41.0 121 43.9 184 38.5

100⬚ 170 55.3 73.3 108 52.5 90.8 121 204 39.2

126 415

56.3

64.7

24.3

27.098⬚

INTERACTIVE

Na2H2P2O7 Na2S2O6 NaC12H25SO3 NaC12H23O2 Na2H2Y · 2H2O Na4Fe(CN)6 NaF Na2BeF4 Na2GeF Na2SiF6

0⬚

LEFT

Sodium acetate aluminum sulfate azide benzoate borate (penta-) borate (tetra-) bromate bromide carbonate chlorate chloride chloroaurate(III) chloroiridate(IV) chromate cyanide dichromate diethyl barbiturate dihydrogen phosphate (ortho-) dihydrogen phosphate (pyro-) dithionate dodecanesulfonate dodecanoate EDTA (Y)* ferrocyanide fluoride fluoroberyllate fluorogermanate fluorosilicate

Formula

(McGHP)

Substance

5.08 2.73 21.5

24.5

5.20

top of page

short standard

base of DF

43.9 14.4 5.9 7.0 1.68 418 17.5 46.0 29.4 2.48 159 44.1 73.0 71.2 2.69 167 1.83 4.5 31.9

50.2 71.5

42.9 93.4 47.7 0.085

102 28.7 49.3 11.1 22.0 566 47.7 119 42.7 100 10.7 191 66.9 94.9 87.6 3.81 222 19.9 16.3 102 111 77.0 94.2 40.8 20.5 35.5 37.2 164 83.2 22.5 39.5 112 58.7

108 37.2 69.5 12.7 55.3

122 65.0 144 16.0 82.8

138 116 186

61.6 129 38.9 110 13.3 205 68.6 102 94.9 4.18 245 30.4 20.2

74.5 174

90.1

19.8 257 71.8 122 111 4.93 288

26.6 295 148 133 5.71 306

29.9

60.0

68.1

77.0

117 81.8 96.5 48.8

130 78.6 91.6 45.3

144 74.8 86.6 43.7

73.0 84.5 42.7

72.7 82.5 42.5

26.6 37.2 49.3 176 104 77.6 26.3 38.3 123 65.3

39.1 32.6 53.8 192

55.0 29.4 88.3 210

33.0 36.8 150 81.8

90.8 40.8 36.1 182 90.5 0.058

92.3

147

160

188

198

102

104

29.5

33.0 302 180 160 6.50 329

65.3 27.9 218 97.2 36.2

36.4 223 101

INTERACTIVE

37.0 85.2 43.5

36.4 4.59 167 64.7 80.8 75.1 3.05 183 5.6 8.2 46.6 44.7 25.2 81.2 9.1 30.0 12.1 19.5 20.0 111 59.7

81.2 23.8 33.9 9.6 7.83 429 34.8 109 43.7 53.4 8.08 178 65.3 87.6 80.8 3.41 201 10.3 12.1 67.8 95.3 26.9 86.2 19.5 44.1 15.7 26.3 27.9 134 70.1 73.0 19.3 41.1 102 52.9 0.090

RIGHT

13.3 78.6 4.9 19.5 9.6 14.4 13.4

62.5 18.8 13.0 8.1 3.53 424 25.3 98

(McGHP)

sulfide sulfite thioantimonate(V) thiocyanate thiosulfate tungstate vanadate Strontium acetate bromide chloride chromate

NaCHO2 Na2GeO3 Na2HAsO4 NaHCO3 Na2HPO4 Na2HPO3 NaC4H5O4 NaOH Na2Sn(OH)6 NaClO NaIO3 NaI Na2MoO4 NaNO3 NaNO2 Na2C2O4 NaClO4 NaIO4 Na3PO4 NaKC4H4O6 NaC7H5O3 Na2SeO4 Na2SeO3 Na2SO4 Na2SO4 · 7H2O Na2S Na2SO3 Na3SbS4 NaSCN Na2S2O3 · 5H2O Na2WO4 NaVO3 Sr(C2H3O2)2 SrBr2 SrCl2 SrCrO4

DEAN #37261

formate germanate hydrogen arsenate hydrogen carbonate hydrogen phosphate hydrogen phosphite hydrogen succinate hydroxide hydroxostannate(IV) hypochlorite iodate iodide molybdate nitrate nitrite oxalate perchlorate periodate phosphate potassium tartrate salicylate selenate selenite sulfate

*Properly called dihydrogen ethylenediaminetetraacetate (Na2H2EDTA · 2H2O).

5.21

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short standard

base of DF

DEAN #37261

TABLE 5.2 Solubilities of Inorganic Compounds and Metal Salts of Organic Acids in Water at Various Temperatures (Continued)

0.0113 9.1 0.91 165 39.5

0.0113 14.7 16.2 66.4 0.171 0.022 2.00 0.21 25.4 0.002 3.90 17.9 6.00 0.135

10⬚

10.6 1.25 52.9

0.0129 18.6 33.8 89.7 0.236 0.032

0.25 29.6 6.22 28.9 8.04

2.73 186

2.17 3.70 187

0.74

0.99

20⬚ 0.0117 12.7 1.77 178 69.5 65 0.0132 21.3 41.6 117 0.364 0.048 5.3 3.92 0.33 35.0 0.006 9.55 40.3 13.1 0.40 2.80 4.87 191 1.38 0.99 11.9

30⬚

40⬚

60⬚

80⬚

90⬚

88.7 72 1.03 0.0138 26.1 50.0 152

17.8 3.95 192 89.4 79 1.05 0.0141 29.5 57.2 198

25.0 8.42 218 93.4 97 3.40 0.0131 37.1 77.5

31.9 20.2 270 96.9 130 9.15 0.0116 47.1 106

32.9 44.5 365 98.4 134 13.13 0.0115

0.068

0.097

0.177 12.2

0.0119 15.2 2.64

14.3 53.2 19.7 0.57

12.750⬚ 0.52 49.4 0.015 21.0 83.6 28.3 0.83

0.80 73.3 0.035 46.1 216 50.8 1.73

6.16

7.53

11.0

4.04 3.00 1.42 9.0 29.2

1.63

1.99 1.17 10.1 17.9

0.42 40.4

2.11 7.7 55.8

36.6 1.20 106 0.070 110 1150 81.5 8.50 14.6

3.04

100⬚

34.4 91.2 383

12.15

155

126 200 750

16.5

3.58

27.2 57.3 1.80 150 0.120 414

10.8 18.4

INTERACTIVE

Tin(II) iodide Uranium(IV) sulfate

SrF2 Sr(CHO2)2 Sr(OH)2 SrI2 Sr(NO3)2 Sr(NO2)2 SrO SrSO4 H2NSO3H H2TeO4 Tb(BrO3)3 · 9H2O TlN3 TlBr Tl2CO3 TlClO3 TlCl TlOH TlI TlNO3 TlNO2 TlClO4 TlOC6H2(NO2)3 Tl2SeO4 Tl2SO4 Th(NO3)4 Th(SO4)2 · 4H2O Th(SO4)2 · 9H2O SnI2 U(SO4)2 · 4H2O U(SO4)2 · 8H2O

0⬚

LEFT

Strontium fluoride formate hydroxide iodide nitrate nitrite oxide sulfate Sulfamic acid Telluric acid Terbium bromate Thallium(I) azide bromide carbonate chlorate chloride hydroxide iodide nitrate nitrite perchlorate picrate selenate sulfate Thorium nitrate sulfate

Formula

(McGHP)

Substance

4.20

5.22

top of page

short standard

base of DF

ZnC4H4O6

98 44.2 63.9 77.3 93.1 8.05 389 145 342 3.70 430 98 41.6

107 0.45 37.5 78.1 106 7.67 152 363 4.30

47.2 54.4

122 0.50 75.1 78.8 123 7.30 446 200 395 5.20 432 53.8 60.0 0.022

141 0.61 22.2 79.6 143 6.78 528 209 437 6.10 138 61.3 65.5 0.041

167 0.80 17.2 87.3 80.8 163 6.09 591 223 452 7.40 445 211 70.5 0.060

317 1.22 10.4 101

388 1.94 6.4 116

200 4.44 618

2.89 645

488 11.8 467

541 21.2 490

75.4

71.1

0.104

426 5.8 123

474 3.16 4.7

2.2 672

28.8

(McGHP)

UO2(NO3)2 UO2C2O4 Yb2(SO4)3 YBr3 YCl3 Y(NO3)3 Y2(SO4)3 ZnBr2 Zn(ClO3)2 ZnCl2 Zn(CHO2)2 ZnI2 Zn(NO3)2 ZnSO4

DEAN #37261

Uranyl nitrate oxalate Ytterbium sulfate Yttrium bromide chloride nitrate sulfate Zinc bromide chlorate chloride formate iodide nitrate sulfate (rh) sulfate (mn) tartrate

614 38.0 510 60.5

0.059

RIGHT INTERACTIVE

5.23

top of page

short standard

base of DF

DEAN #37261

LEFT

(McGHP)

5.24

INTERACTIVE

top of rh base of rh

SECTION 5

5.2

cap height base of text

VAPOR PRESSURES

TABLE 5.3 Vapor Pressure of Mercury Temp. ⬚C 0

mm of Hg 0.000 185

2 4 6 8 10

0.000 0.000 0.000 0.000 0.000

228 276 335 406 490

12 14 16 18 20

0.000 0.000 0.000 0.001 0.001

588 706 846 009 201

22 24 26 28 30

0.001 0.001 0.002 0.002 0.002

426 691 000 359 777

32 34 36 38 40

0.003 0.003 0.004 0.005 0.006

261 823 471 219 079

42 44 46 48 50

0.007 0.008 0.009 0.010 0.012

067 200 497 98 67

52 54 56 58 60

0.014 0.016 0.019 0.022 0.025

59 77 25 06 24

62 64 66 68 70

0.028 0.032 0.037 0.042 0.048

83 87 40 51 25

72 74 76 78 80

0.054 0.061 0.069 0.078 0.088

69 89 93 89 80

82 84 86 88 90

0.100 0 0.112 4 0.126 1 0.1413 0.1582

Temp. ⬚C

mm of Hg

Temp. ⬚C

mm of Hg

92 94 96 98 100

0.1769 0.1976 0.2202 0.2453 0.2729

184 186 188 190

10.116 10.839 11.607 12.423

102 104 106 108 110

0.3032 0.3366 0.3731 0.4132 0.4572

192 194 196 198 200

13.287 14.203 15.173 16.200 17.287

112 114 116 118 120

0.5052 0.5576 0.6150 0.6776 0.7457

202 204 206 208 210

18.437 19.652 20.936 22.292 23.723

122 124 126 128 130

0.8198 0.9004 0.9882 1.084 1.186

212 214 216 218 220

25.233 26.826 28.504 30.271 32.133

132 134 136 138 140

1.298 1.419 1.551 1.692 1.845

222 224 226 228 230

34.092 36.153 38.318 40.595 42.989

142 144 146 148 150

2.010 2.188 2.379 2.585 2.807

232 234 236 238 240

45.503 48.141 50.909 53.812 56.855

152 154 156 158 160

3.046 3.303 3.578 3.873 4.189

242 244 246 248 250

60.044 63.384 66.882 70.543 74.375

162 164 166 168 170

4.528 4.890 5.277 5.689 6.128

252 254 256 258 260

78.381 82.568 86.944 91.518 96.296

172 174 176 178 180

6.596 7.095 7.626 8.193 8.796

182

9.436

262 264 266 268 270

101.28 106.48 111.91 117.57 123.47

272 274

129.62 136.02

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.25

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.3 Vapor Pressure of Mercury (Continued) Temp. ⬚C

mm of Hg

276 278 280

142.69 149.64 156.87

282 284 286 288 290

164.39 172.21 180.34 188.79 197.57

292 294 296 298 300

206.70 216.17 226.00 236.21 246.80

302 304 306 308 310

257.78 269.17 280.98 293.21 305.89

312 314 316 318 320

319.02 332.62 346.70 361.26 376.33

322 324 326 328 330

391.92 408.04 424.71 441.94 459.74

Temp. ⬚C

top of rh base of rh

mm of Hg

332 334 336 338 340

478.13 497.12 516.74 537.00 557.90

342 344 346 348 350

579.45 601.69 624.64 648.30 672.69

352 354 356 358 360

697.83 723.73 750.43 777.92 806.23

362 364 366 368 370

835.38 865.36 896.23 928.02 960.66

372 374 376 378 380

994.34 1028.9 1064.4 1100.9 1138.4

382 384 386

1177.0 1216.6 1257.3

Temp. ⬚C

mm of Hg

388 390

1299.1 1341.9

392 394 396 398 400

1386.1 1431.3 1477.7 1525.2 1574.1

430 460 490

2464 3715 5420

520 550 600 650 700 750 800 850 900* 950 1000 1050 1100 1150 1200 1250 1300

7691 10650 22.87 atm 35.49 atm 52.51 atm 74.86 103.31 138.42 180.92 226.58 290.5 358.1 437.3 521.3 616.8 721.4 835.9

atm atm atm atm atm

atm atm atm atm atm atm atm

* Critical point.

short standard long

DEAN #37261

LEFT

(McGHP)

5.26

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.4 Vapor Pressure of Ice in Millimeters of Mercury For temperatures from ⫺ 99 to 0⬚C. The values in the table are for ice in contact with its own vapor. Where the ice is in contact with air at a temperature t⬚C, this correction must be added: Correction ⫽ 20p/(100)(t ⫹ 273). t, ⬚C ⫺99 ⫺98 ⫺97 ⫺96 ⫺95 ⫺94 ⫺93 ⫺92 ⫺91 ⫺90 ⫺89 ⫺88 ⫺87 ⫺86 ⫺85 ⫺84 ⫺83 ⫺82 ⫺81 ⫺80 ⫺79 ⫺78 ⫺77 ⫺76 ⫺75 ⫺74 ⫺73 ⫺72 ⫺71 ⫺70 ⫺69 ⫺68 ⫺67 ⫺66 ⫺65 ⫺64 ⫺63 ⫺62 ⫺61 ⫺60 ⫺59 ⫺58 ⫺57 ⫺56 ⫺55 ⫺54 ⫺53 ⫺52

p, mm Hg 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.001 0.001 0.001 0.001 0.001 0.002 0.002 0.003 0.003 0.004 0.004 0.005 0.006 0.007 0.008 0.009 0.010 0.012 0.013 0.015 0.017 0.020 0.023

012 015 018 022 027 033 040 048 058 070 084 10 12 14 17 20 24 29 34 40 47 56 66 77 90 05 23 43 67 94 25 61 02 49 03 64 34 14 03 08 25 6 1 8 7 8 3 0

t, ⬚C ⫺51 ⫺50 ⫺49 ⫺48 ⫺47 ⫺46 ⫺45 ⫺44 ⫺43 ⫺42 ⫺41 ⫺40 ⫺39 ⫺38 ⫺37 ⫺36 ⫺35 ⫺34 ⫺33 ⫺32 ⫺31 ⫺30.0 ⫺29.5 ⫺29.0 ⫺28.5 ⫺28.0 ⫺27.5 ⫺27.0 ⫺26.5 ⫺26.0 ⫺25.5 ⫺25.0 ⫺24.5 ⫺24.0 ⫺23.5 ⫺23.0 ⫺22.5 ⫺22.0 ⫺21.5 ⫺21.0 ⫺20.5 ⫺20.0 ⫺19.5 ⫺19.0 ⫺18.5 ⫺18.0 ⫺17.5 ⫺17.0

p, mm Hg 0.026 1 0.029 6 0.033 4 0.037 8 0.042 6 0.048 1 0.054 1 0.060 9 0.068 4 0.076 8 0.086 2 0.096 6 0.108 1 0.120 9 0.135 1 0.150 7 0.168 1 0.187 3 0.208 4 0.231 8 0.257 5 0.285 9 0.301 0.317 0.334 0.351 0.370 0.389 0.409 0.430 0.453 0.476 0.500 0.526 0.552 0.580 0.609 0.640 0.672 0.705 0.740 0.776 0.814 0.854 0.895 0.939 0.984 1.031

t, ⬚C ⫺16.5 ⫺16.0 ⫺15.5 ⫺15.0 ⫺14.5 ⫺14.0 ⫺13.5 ⫺13.0 ⫺12.5 ⫺12.0 ⫺11.5 ⫺11.0 ⫺10.5 ⫺10.0 ⫺9.8 ⫺9.6 ⫺9.4 ⫺9.2 ⫺9.0 ⫺8.8 ⫺8.6 ⫺8.4 ⫺8.2 ⫺8.0 ⫺7.8 ⫺7.6 ⫺7.4 ⫺7.2 ⫺7.0 ⫺6.8 ⫺6.6 ⫺6.4 ⫺6.2 ⫺6.0 ⫺5.8 ⫺5.6 ⫺5.4 ⫺5.2 ⫺5.0 ⫺4.8 ⫺4.6 ⫺4.4 ⫺4.2 ⫺4.0 ⫺3.8 ⫺3.6 ⫺3.4 ⫺3.2

p, mm Hg 1.080 1.132 1.186 0.241 1.300 1.361 1.424 1.490 1.559 1.632 1.707 1.785 1.866 1.950 1.985 2.021 2.057 2.093 2.131 2.168 2.207 2.246 2.285 2.326 2.367 2.408 2.450 2.493 2.537 2.581 2.626 2.672 2.718 2.765 2.813 2.862 2.912 2.962 3.013 3.065 3.117 3.171 3.225 3.280 3.336 3.393 3.451 3.509

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.27

PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.4 Vapor Pressure of Ice in Millimeters of Mercury (Continued) t, ⬚C

p, mm Hg

t, ⬚C

p, mm Hg

t, ⬚C

p, mm Hg

⫺3.0 ⫺2.8 ⫺2.6 ⫺2.4 ⫺2.2 ⫺2.0

3.568 3.360 3.691 3.753 3.816 3.880

⫺1.8 ⫺1.6 ⫺1.4 ⫺1.2 ⫺1.0

3.946 4.012 4.079 4.147 4.217

⫺0.8 ⫺0.6 ⫺0.4 ⫺0.2 0.0

4.287 4.359 4.431 4.504 4.579

TABLE 5.5 Vapor Pressure of Liquid Ammonia, NH3 t⬚C.

p in atm

t⬚C.

p in atm

t⬚C.

p in atm

⫺78 ⫺76 ⫺74 ⫺72 ⫺70

0.0582 0.0683 0.0797 0.0929 0.1078

⫺6 ⫺4 ⫺2 0 ⫹2

3.3677 3.6405 3.9303 4.2380 4.5640

66 68 70 72 74

29.784 31.211 32.687 34.227 35.813

⫺68 ⫺66 ⫺64 ⫺62 ⫺60

0.1246 0.1437 0.1651 0.1891 0.2161

4 6 8 10 12

4.9090 5.2750 5.6610 6.0685 6.4985

76 78 80 82 84

37.453 39.149 40.902 42.712 44.582

⫺58 ⫺56 ⫺54 ⫺52 ⫺50

0.2461 0.2796 0.3167 0.3578 0.4034

14 16 18 20 22

6.9520 7.4290 7.9310 8.4585 9.0125

86 88 90 92 94

46.511 48.503 50.558 52.677 54.860

⫺48 ⫺46 ⫺44 ⫺42 ⫺40

0.4536 0.5087 0.5693 0.6357 0.7083

24 26 28 30 32

9.5940 10.2040 10.8430 11.512 12.212

96 98 100 102 104

57.111 59.429 61.816 64.274 66.804

⫺38 ⫺36 ⫺34 ⫺32 ⫺30

0.7875 0.8738 0.9676 1.0695 1.1799

34 36 38 40 42

12.943 13.708 14.507 15.339 16.209

106 108 110 112 114

69.406 72.084 74.837 77.668 80.578

⫺28 ⫺26 ⫺24 ⫺22 ⫺20

1.2992 1.4281 1.5671 1.7166 1.8774

44 46 48 50 52

17.113 18.056 19.038 20.059 21.121

116 118 120 122 124

83.570 86.644 89.802 93.045 96.376

⫺18 ⫺16 ⫺14 ⫺12 ⫺10 ⫺8

2.0499 2.2349 2.4328 2.6443 2.8703 3.1112

54 56 58 60 62 64

22.224 23.372 24.562 25.797 27.079 28.407

126 128 130 132 132.3

99.796 103.309 106.913 110.613 111.3(c.p.)

short standard long

DEAN #37261

LEFT

(McGHP)

5.28

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.6 Vapor Pressure of Water For temperatures from ⫺ 10 to 120⬚C. The values in the table are for water in contact with its own vapor. Where the water is in contact with air at a temperature t in degrees Celsius, the following correction must be added: Correction (when t ⱕ 40⬚C) ⫽ p(0.775 ⫺ 0.000 313t)/100; correction (when t ⬎ 50⬚C) ⫽ p(0.0652 ⫺ 0.000 087 5t)/100. t, ⬚C ⫺10.0 ⫺9.5 ⫺9.0 ⫺8.5 ⫺8.0 ⫺7.5 ⫺7.0 ⫺6.5 ⫺6.0 ⫺5.5 ⫺5.0 ⫺4.5 ⫺4.0 ⫺3.5 ⫺3.0 ⫺2.5 ⫺2.0 ⫺1.5 ⫺1.0 ⫺0.5 0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0 11.5 12.0 12.5

p, mm Hg 2.149 2.236 2.326 2.418 2.514 2.613 2.715 2.822 2.931 3.046 3.163 3.284 3.410 3.540 3.673 3.813 3.956 4.105 4.258 4.416 4.579 4.750 4.926 5.107 5.294 5.486 5.685 5.889 6.101 6.318 6.543 6.775 7.013 7.259 7.513 7.775 8.045 8.323 8.609 8.905 9.209 9.521 9.844 10.176 10.518 10.870

t, ⬚C 13.0 13.5 14.0 14.5 15.0 15.2 15.4 15.6 15.8 16.0 16.2 16.4 16.6 16.8 17.0 17.2 17.4 17.6 17.8 18.0 18.2 18.4 18.6 18.8 19.0 19.2 19.4 19.6 19.8 20.0 20.2 20.4 20.6 20.8 21.0 21.2 21.4 21.6 21.8 22.0 22.2 22.4 22.6 22.8 23.0 23.2

p, mm Hg 11.231 11.604 11.987 12.382 12.788 12.953 13.121 13.290 13.461 13.634 13.809 13.987 14.166 13.347 14.530 14.715 14.903 15.092 15.284 15.477 15.673 15.871 16.071 16.272 16.477 16.685 16.894 17.105 17.319 17.535 17.753 17.974 18.197 18.422 18.650 18.880 19.113 19.349 19.587 19.827 20.070 20.316 20.565 20.815 21.068 21.324

t, ⬚C 23.4 23.6 23.8 24.0 24.2 24.4 24.6 24.8 25.0 25.2 25.4 25.6 25.8 26.0 26.2 26.4 26.6 26.8 27.0 27.2 27.4 27.6 27.8 28.0 28.2 28.4 28.6 28.8 29.0 29.2 29.4 29.6 29.8 30.0 30.2 30.4 30.6 30.8 31.0 31.2 31.4 31.6 31.8 32.0 32.2 32.4

p, mm Hg 21.583 21.845 22.110 22.387 22.648 22.922 23.198 23.476 23.756 24.039 24.326 24.617 24.912 25.209 25.509 25.812 26.117 26.426 26.739 27.055 27.374 27.696 28.021 28.349 28.680 29.015 29.354 29.697 30.043 30.392 30.745 31.102 31.461 31.824 32.191 32.561 32.934 33.312 33.695 34.082 34.471 34.864 35.261 35.663 36.068 36.477

t, ⬚C 32.6 32.8 33.0 33.2 33.4 33.6 33.8 34.0 34.2 34.4 34.6 34.8 35.0 35.2 35.4 35.6 35.8 36.0 36.2 36.4 36.6 36.8 37.0 37.2 37.4 37.6 37.8 38.0 38.2 38.4 38.6 38.8 39.0 39.2 39.4 39.6 39.8 40.0 40.5 41.0 41.5 42.0 42.5 43.0 43.5 44.0

p, mm Hg 36.891 37.308 37.729 38.155 38.584 39.018 39.457 39.898 40.344 40.796 41.251 41.710 42.175 42.644 43.117 43.595 44.078 44.563 45.054 45.549 46.050 46.556 47.067 47.582 48.102 48.627 49.157 49.692 50.231 50.774 51.323 51.879 52.442 53.009 54.580 54.156 54.737 55.324 56.81 58.34 59.90 61.50 63.13 64.80 66.51 68.26

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TABLE 5.6 Vapor Pressure of Water (Continued) t, ⬚C 44.5 45.0 45.5 46.0 46.5 47.0 47.5 48.0 48.5 49.0 49.5 50.0 50.5 51.0 51.5 52.0 52.5 53.0 53.5 54.0 54.5 55.0 55.5 56.0 56.5 57.0 57.5 58.0 58.5 59.0 59.5 60.0 60.5 61.0 61.5 62.0 62.5

p, mm Hg 70.05 71.88 73.74 75.65 77.61 79.60 81.64 83.71 85.85 88.02 90.24 92.51 94.86 97.20 99.65 102.09 104.65 107.20 109.86 112.51 115.28 118.04 120.92 123.80 126.81 129.82 132.95 136.08 139.34 142.60 145.99 149.38 152.91 156.43 160.10 163.77 167.58

t, ⬚C 63.0 63.5 64.0 64.5 65.0 65.5 66.0 66.5 67.0 67.5 68.0 68.5 69.0 69.5 70.0 70.5 71.0 71.5 72.0 72.5 73.0 73.5 74.0 74.5 75.0 75.5 76.0 76.5 77.0 77.5 78.0 78.5 79.0 79.5 80.0 80.5 81.0

p, mm Hg 171.38 175.35 179.31 183.43 187.54 191.82 196.09 200.53 204.96 209.57 214.17 218.95 223.73 228.72 233.7 238.8 243.9 249.3 254.6 260.2 265.7 271.5 277.2 283.2 289.1 295.3 301.4 307.7 314.1 320.7 327.3 334.2 341.0 348.1 355.1 362.4 369.7

top of rh base of rh

t, ⬚C 81.5 82.0 82.5 83.0 83.5 84.0 84.5 85.0 85.5 86.0 86.5 87.0 87.5 88.0 88.5 89.0 89.5 90.0 90.5 91.0 91.5 92.0 92.5 93.0 93.5 94.0 94.5 95.0 95.2 95.4 95.6 95.8 96.0 96.2 96.4 96.6 96.8

p, mm Hg

t, ⬚C

p, mm Hg

377.3 384.9 392.8 400.6 408.7 416.8 425.2 433.6 442.3 450.9 459.8 468.7 477.9 487.1 496.6 506.1 515.9 525.76 535.83 546.05 556.44 566.99 577.71 588.60 599.66 610.90 622.31 633.90 638.59 643.30 648.05 652.82 657.62 662.45 667.31 672.20 677.12

97.0 97.2 97.4 97.6 97.8 98.0 98.2 98.4 98.6 98.8 99.0 99.2 99.4 99.6 99.8 100.0 101.0 102.0 103.0 104.0 105.0 106.0 107.0 108.0 109.0 110.0 111.0 112.0 113.0 114.0 115.0 116.0 117.0 118.0 119.0 120.0

682.07 687.04 692.05 697.10 702.17 707.27 712.40 717.56 722.75 727.98 733.24 738.53 743.85 749.20 754.58 760.00 787.57 815.86 845.12 875.06 906.07 937.92 970.60 1004.42 1038.92 1074.56 1111.20 1148.74 1187.42 1227.25 1267.98 1309.94 1352.95 1397.18 1442.63 1489.14

TABLE 5.7 Vapor Pressure of Deuterium Oxide t, ⬚C

p, mm Hg

0 1 2 3 3.8 10

3.65 3.93 4.29 4.65 5.05 7.79

t, ⬚C

p, mm Hg

20 30 40 50 60 70

15.2 28.0 49.3 83.6 136.6 216.1

t, ⬚C 80 90 100 101.43

p, mm Hg 331.6 495.5 722.2 760.0

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Vapor-Pressure Equations

Numerous mathematical formulas relating the temperature and pressure of the gas phase in equilibrium with the condensed phase have been proposed. The Antoine equation (Eq. 1) gives good correlation with experimental values. Equation 2 is simpler and is often suitable over restricted temperature ranges. In these equations, and the derived differential coefficients for use in the Haggenmacher and Clausius-Clapeyron equations, the p term is the vapor pressure of the compound in pounds per square inch (psi), the t term is the temperature in degrees Celsius, and the T term is the absolute temperature in kelvins (t⬚C ⫹ 273.15).

Eq.

Vapor-pressure equation

⫺[d(ln p)/d(1/T)]

dp/dT

1

log p ⫽ A ⫺

B t⫹C

2.303pB (t ⫹ C)2

2.303BT 2 (t ⫹ C)2

2

log p ⫽ A ⫺

B T

2.303pB T2

2.303B

3

log p ⫽ A ⫺

B ⫺ C log T T

p

冉

2.303B C ⫺ T2 T

冊

2.303B ⫺ CT

Equations 1 and 2 are easily rearranged to calculate the temperature of the normal boiling point: t⫽

B ⫺C A ⫺ log p

(5.1)

T⫽

B A ⫺ log p

(5.2)

The constants in the Antoine equation may be estimated by selecting three widely spaced data points and substituting in the following equations in sequence:

冉

冊冉 冊 冉 冉 冊 冉 冊

y3 ⫺ y2 y2 ⫺ y1 B⫽

t 2 ⫺ t1 t3 ⫺ t2

y3 ⫺ y1 t 3 ⫺ t1

A ⫽ y2 ⫹

⫽1⫺

t 3 ⫺ t1 t3 ⫹ C

冊

(t1 ⫹ C)(t 3 ⫹ C)

B t2 ⫹ C

In these equations, yi ⫽ log pi .

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TABLE 5.8 Vapor Pressures of Various Inorganic Compounds Substance Aluminum AlCl3 Al2O3 Ammonium NH3 NH4Br NH4Cl NH4I NH4N3 Antimony Sb SbBr3 SbCl3 SbI3 Sb2Se3 Argon Ar

State

CdI2 Calcium Ca

* Crystalline solid.

2 2

70– 190 1840– 2000

1 1 1 1 1 1

c

subl c

2 2 2 2 2

c liq

1 1

1070– 1325 235– 324 170– 253 330– 445

A

16.24 14.22

B

9.963 82 7.360 50 9.220 0 9.355 7 9.147 0 10.433 4

1 617.907 926.132 3 947 3 703.7 3 858 2 821.0

9.051 8.005 8.090 7.831 8.790 6

9 871 2 873 2 582.3 3 350.55 6 432.3

7.505 81 6.616 51

399.085 304.227

440– 815 800– 860 50– 100 100– 310 315– 490

10.800 6.692 7.953 12.127 6.513

2 2

930– 1130 500– 1000

15.765 6.86

2 2

1210– 1420 91– 213

8.876 2.681

⫺40 to 90

liq liq

2 1 2 1 2

7.655 6.188 11 7.459 5 6.366 38 7.901

1 740.3 756.89 1 157.99 521.490 1 690.3

c liq liq liq liq

1 1 1 1 1

9.7209 6.877 80 7.729 74 7.273 68 7.436 51

2 041.3 1 119.68 1 673.95 1 219.28 1 195.8

⫺118 to ⫺20 ⫺43 to 8.4

C

6 006 28 200

2 2 2 2 2

AsCl3 As2O3

BrF3 BrF5 BrO2F Cadmium Cd

Range, ⬚C

c* liq subl c subl c subl c c

Arsenic As

Barium Ba BaH2 [97% pure] Bismuth Bi BiCl3 Boron BBr3 BCl3 B(CH3)3 B2H6 B5H11 Bromine Br2

Eq.

top of rh base of rh

272.55 240.17 227.0 232.0 226.0 240.0

272.63 267.32

6 947 2 460 2 042.7 5 815.81 2 722.2 18 280 4 000 10 446 685.519

2 2 2

150– 321 500– 840 385– 450

8.564 7.897 9.269

5 693 5 218 6 383

2 2

500– 700 960– 1100

9.697 16.240

10 185 19 325

214.0 241.98

260.1 221.38 219.48 236.40 260.1

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TABLE 5.8 Vapor Pressures of Various Inorganic Compounds (Continued) Substance Carbon C [as C(g)] [as C2(g)] [all species] Carbon CNBr CNF CO CO2 C3O2 COCl2 COF2 COS CS2 CSe2 CSeS Cesium Cs CsBr CsCl CsF CsH CsI Chlorine Cl2 ClF ClF3 ClF5 ClO2 Cl2O ClOClO3 Cl2O7 ClO2F ClO3F Copper CuBr CuCl CuI Fluorine F2 FNO3 Germanium GeCl4 Helium 3 He 4

He

State

Eq.

Range, ⬚C

liq liq liq

1 1 1

subl c

1 1 1 1 1 1 1 1 1 1 1 1

⫺109 to ⫺84 ⫺111 to ⫺49 3– 80 0– 50 ⫺16 to 84

2 2 2 2 2 2 2

200– 350 978– 1305 986– 1295 1033– 1255 245– 378 340– 440 1052– 1280

cI liq c liq liq

c liq liq liq liq liq liq liq liq liq

liq liq

liq liq

11.042 8 12.583 2 9.381 3 ⫺76 to ⫺47

⫺71 to 7

1 1 1 1 1 1 1 1 1 1 1 2 2 2

A

997– 1351 878– 1369 991– 1154

1 1

9.488 9 6.778 9 7.414 8 6.694 22 9.810 66 7.188 99 6.971 33 6.885 5 6.907 23 6.942 79 6.776 73 6.699 6 6.949 7.990 8.340 7.703 11.79 9.25 9.124

10.4– 86

1 1 1 1 1

⫺271.13 to ⫺270.86 ⫺271.13 to ⫺269.92 ⫺271.4 to ⫺270.1 ⫺271.4 to ⫺268.9 ⫺271.4 to ⫺268.1

C

37 736 43 281 27 240

302.2 318.3 264.0

2 041.8 697.61 342.50 291.743 1 347.786 1 100.94 998.770 576.70 804.48 1 169.11 1 353.20 1 161.97

1 444.19 861.34 682.1 1 096.28 653.06 590.09 1 021.56 1 404.18 1 214.00 809.78 791.73

5.460 5.454 5.570

4 173.2 4 215.0 4 215.0

7.340 4.272 7 5.100 0 4.558 7 5.320 75 6.004 60

251.70 224.95 269.0 267.99 273.00 249.15 236.68 228.58 250.0 241.59 219.95 219.59

3 833.7 8 022.53 8 523.94 7 359.21 5 900 4 410 9 699.11

9.705 12 6.937 90 6.989 7.366 85 6.269 33 6.036 11 7.132 68 7.538 67 6.869 29 6.677 15 6.895 19

6.765 88 6.658 6

2

B

304.35 769.5

267.13 246.33 256 232.63 206.6 176.15 238.16 257.00 220.79 218.96 243.88

266.54 248.0

2 010.9 5.594 11.062 8.1548 14.6515 24.0668

273.840 274.950 273.710 274.950 276.650

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TABLE 5.8 Vapor Pressures of Various Inorganic Compounds (Continued) Substance Hydrogen 1 H2 normal, 25% para equilibrium 1

H2H (DH)

2

H2 (D2) normal, 66.7% ortho 2 H2 equilibrium, 97.8% ortho 3 H2 (T2) normal, 25% para 1HBr 2

HBr (DBr)

1

HCl

2

HCl (DCl)

HCN 1HF 2HF (DF) 1 HI 2

HI (DI)

HN3 HNO3 1H O 2 2 H2O (D2O) H218O H2O2 HPO2F H2S H2S2 H2S3 H2S4 H2S5 HSO3Cl HSO3F H2Se H2Te Iodine I2 ICl IF5 IF7

State

Eq.

c liq c liq c liq c liq c liq c liq c liq c liq c liq c liq liq liq liq c liq c liq liq liq

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

liq liq c liq liq liq liq liq liq liq c liq liq

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

c liq liq c liq c

1 1 1 1 1 1

Range, ⬚C

A

6.043 86 5.824 38 6.042 07 5.814 64 6.960 08 6.016 12 7.726 05 6.128 25 7.751 10 6.044 68 6.184 03 6.089 21 7.667 61 6.287 53 7.500 93 6.162 38 8.134 73 7.170 00 7.850 47 6.935 96 ⫺16 to 46 7.528 2 7.680 98 7.217 04 7.315 6 5.608 9 7.314 9 5.601 8 6.857 7.511 9 [See Tables 5.4 and 5.6] [See Table 5.7] 0– 60 8.133 2 60– 120 7.972 08 7.969 17 6.735 3 7.614 18 6.993 92 6.974 6.807 6.945 7.320 7.049 7.399 5 7.635 4 6.966 0 7.000 9.810 9 7.018 1 7.702 1 10.964 7.464 8 7.998

top of rh base of rh

B

C

66.507 67.5078 65.961 66.7945 99.968 77.1349 135.461 83.5251 135.58 79.5888 76.7445 81.8971 878.57 540.82 820.68 505.68 941.57 745.80 843.32 668.20 1329.5 1475.60 1268.37 894.32 416.04 889.52 413.98 1 066 1 406

274.630 275.700 274.60 275.650 276.590 275.620 278.550 275.216 278.50 274.680 271.850 273.650 253.2 225.44 247.3 220.6 268.06 258.88 258.32 249.50 260.4 287.88 273.87 239.6 188.1 238.8 187.8 232 221.0

1 762.39 1 668.84 1 886.76 1 342.9 885.319 768.130 1 232 1 488 1 772 2 104 1 480 1 521 927.6 787.67 935

235.660 227.700 220.6 232.0 250.25 249.09 225 209 196 189 201 174.0 240.0 235.0 229

2 901.0 1 610.9 1 517.9 2 538 1 460 1 340

256.00 205.0 217.0 245 216.0 256

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TABLE 5.8 Vapor Pressures of Various Inorganic Compounds (Continued) Substance Iridium IrF6 Iron FeCl2 FeCl3 FeI2 Krypton Kr

Eq.

Range, ⬚C

A

c liq

2 2

0.4– 44 44– 54

8.618 7.952

1 868 1 657

liq liq c

2 2 2 2 2

708– 834 700– 930 160– 304 517– 577 601– 686

9.794 8.33 15.11 13.183 9.674

7 455 7 061 7 142 10 778 7 716

c liq

1 1

State

Lead Pb PbBr2 PbCl2 PbF2 Lithium LiBr LiCl LiF LiH LiI Magnesium Mg MgH2 Mercury Hg HgBr2 HgCl2 Hg2Cl2 HgI2 Neon Ne Neptunium NpF6 Nickel Ni(CO)4 Niobium NbBr5 NbCl5 NbF5 Nitrogen N2 natural 15

N2

NCl3 NF3 NH3

7.539 55 6.630 70

539.48 416.38

2 2 2 2

525– 1325 735– 918 500– 950 1078– 1289

7.827 8.064 8.961 8.391

9 845.4 6 163.1 7 411.4 8 623.2

2 2 2 2 2 2

1010– 1265 1045– 1325 1398– 1666 500– 650 700– 800 940– 1140

8.068 7.939 8.753 11.227 9.926 8.011

7 975.5 8 142.7 11 407 9 600 8 204 7 500

2 2

900– 1070 337– 415

12.993 9.78

13 579.8 3 857

2 2 2 1 2

130– 270 130– 270 275– 309

[See Table 5.3] 10.094 10.094 8.409 8.521 51 266– 360 8.115

c liq

1 1

liq

3

55.1– 76.8

2 liq liq liq

2 2 2

c liq c liq

1 1 1 1 1 1

liq

B

7.065 16 6.084 44

4 168.0 4 118.34 3 187.1 3 110.96 3 278.5 110.61 78.380

0.010 23

1 191.1

2– 40

7.780

1 556.5

210– 254

8.92 8.37 8.439

3 850 2 827 2 824

7.345 12 6.494 57 7.363 96 6.494 14 6.956 6.779 66 [See Table 5.5]

322.222 255.680 323.17 255.535 1 190 501.913

C

269.8 264.45

168.0

272.00 270.550 ⫺2.582 5

269.980 266.550 269.88 266.451 221 257.79

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TABLE 5.8 Vapor Pressures of Various Inorganic Compounds (Continued) Substance Nitrogen (continued) N2H4 NO natural N2O N2O4 equilibrium mixture N2O5 NOCl N2O3 NOF NO2Cl NO2F Osmium OsF5 OsF6 OsF8 OsO4 OsO3F2 Oxygen O2 O3 OF2 O2F2 O3F2 Palladium PdCl2 Phosphorus P red, V white P4 black, o-rh PBr3 PBr5 PBrF2 PBr2F PCl3 PCl5 PClF2 PCl2F P(OCN)3 PF3 PF5 PH3 P2H4 P4O6 P4O10

POBr3

State

liq c liq c liq c liq c c liq liq liq liq

Eq.

1 1 1 1 1 1 1 1 1 1 2 1 1 1 2 2 2 2 2

liq liq liq liq

subl c subl c liq liq liq liq liq c liq liq liq liq liq liq c liq liq liq c III cI liq liq

Range, ⬚C

⫺25 to 0

75– 180 34– 48 38– 47 ⫺38 to 40 59– 105

1 1 1 1 2

79– 114

2

680– 857

1 1 1 1 1 1 1 1 1 1 1 1 2 1 1 1 1 1 1 1 1 1 1

⫺40 to 173 to 104 ⫺133 to ⫺16 ⫺115 to 78 ⫺92 to 76 to 160 ⫺165 to ⫺47 ⫺144 to 14 ⫺2 to 169 ⫺152 to ⫺101 ⫺93.8 to ⫺84.5

24– 175

51– 192

A

B

7.801 9 9.628 26 8.743 00 9.437 00 7.003 94 10.736 31 8.917 12 11.644 5 8.540 8 7.361 54 10.30 6.443 5 5.372 3 6.833 4

1 679.07 758.736 682.938 1 174.020 654.260 2 075.53 1 798.54 2 510 1 397.3 1 094.73 2 057.9 556.13 395.40 654.55

9.75 7.470 7.650 10.710 0 7.994

3 429 1 473 1 525 2 951.00 1 911

6.691 44 6.837 7.236 19 6.779 02 6.134 3 6.32 11.060 6.936 9 12.405 6.915 5 6.948 6.904 2 6.858 0 6.826 7 10.206 8 7.033 6.639 6 6.796 56 8.745 5 6.860 4 6.914 4 7.482 35 6.715 59 6.862 8 6.716 37 9.707 0 10.843 2 6.935 2 7.007 8

top of rh base of rh

319.013 552.5 545.05 756.39 675.57

C

227.7 266.00 268.27 268.22 247.16 252.80 276.80 253.0 261.0 249.70 216.0 174.0 238.0

266.697 251.0 269.91 250.16

5 032 5 323 1 907.6 6 671 1 590.5 1 320 885.12 1 210.3 1 196 2 903.1 1 490 780.88 982.332 2 595 620.22 647.21 794.496 645.512 1 137 1 412.8 3 822 6 424 3 069 1 609.2

220 190.0 247 221.0 214 236.0 226.0 227.0 237.0 200.0 255.0 237.00 257.0 245.0 265.20 256.066 227.0 193.0 201.0 213 152 198.0

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TABLE 5.8 Vapor Pressures of Various Inorganic Compounds (Continued) Substance Phosphorus (continued) POBrCl2 POBrClF POBrF2 POBr2F POCl3 POClF2 POCl2F POF3 PO(OCN)3 PO(SCN)3 P4S10 PSBr3 PS(OCN)3 Platinum Pt PtF6 Polonium Po PoCl4 Potassium K KBr KCl KF KOH KI Protactinium Radon Rn Rhenium ReF5 ReF6 ReF7 ReO2 ReO3 Re2O7 ReOF4 ReOF5 ReS2 Re2S7 Rubidium Rb RbCl RbF

State

liq liq liq liq liq liq liq c liq

c liq

Eq.

Range, ⬚C

1 1 1 1 1 1 1 1 1 2 2 2 2 2 2

31– 165 ⫺85 to 32 ⫺117 to 110 1.2– 105 ⫺96 to 3 ⫺80 to 53

5– 193 14– 300

liq

2 1

1425– 1765 61.3– 81.7

liq liq

1 1

liq

2 2 2 2 2 2 2

c liq

1 1

c c liq c liq c liq c liq liq liq liq c c

2 3 3 3 3 2 2 2 2 2 2 2 2 2

⫺3.45 to 18.5 18.5– 48 ⫺14.5 to 48.3 48.3– 74.6 650– 785 480– 660 325– 420 300– 480 230– 360 108– 172 41– 73 500– 700 260– 410

2 2 2

250– 370 1142– 1395 1142– 1400

A

6.924 6.914 7.101 9 6.721 2 6.865 8 6.926 6 7.084 65 10.930 5 7.115 5 9.168 2 8.533 0 9.17 10.105 8.338 3 10.032 7.786 89.15 7.041 4 7.554

260– 760 1095– 1375 1116– 1418 1278– 1500 1170– 1327 1063– 1333

7.183 7.936 8.130 9.000 7.330 7.949 17.27

B

1 411 1 214 1 118.9 1 328.9 1 297.2 946.96 1 201.86 1 783 810.1 2 931 3 240 4 940 3 196.2 2 641.9 3 492 25 384 5 686 5 017.6 2 360

213 222 233.0 236.0 220.0 231.0 233.00 261.0 231.0

27.49 241.0 115

4 434.33 8 555.3 8 863.4 10 838 7 103.3 8 132.2 7 377

7.495 5 6.701 5

884.41 718.25

9.024 9.123 0 18.208 1 13.043 2 ⫺21.583 5 11.65 5.345 15.16 7.745 8.98 10.09 7.727 3.214 8.86

3 037 1 765.4 1 956.7 2 205.8 244.28 14 437 4 742 10 882 4 966 3 868 3 206 1 679 4 976 4 800

6.976 9.111 8.570

C

3 969.5 10 373 9 568.4

255.0 250.0

0.1790 3.599 1.470 3 ⫺9.908 3

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.37

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.8 Vapor Pressures of Various Inorganic Compounds (Continued) Substance Ruthenium RuOF4 Selenium Se SeCl4 SeF4 SeF6 SeO2 SeOCl2 SeOF2 Silicon SiCl4 SiH4 Si2H6 Si3H8 Silver AgCl Sodium Na NaCl NaCI NaCN NaF NaI NaOH Strontium Sr Sulfur S equilibrium S2Br2 SCl2 S2Cl2 S2F2 SF4 SF6 S2F10 SO2 SO3 “icelike” “woollike”

SOBr2 SOCl2 SOClF SOF2 SOF4 S2O2F10 S2O5Cl2 S2O5ClF S2O5F2 S2O5F4

State

liq c liq c liq liq liq

liq liq liq liq liq liq c liq c liq c III c II cI liq liq liq liq liq liq liq liq liq liq liq

Eq.

Range, ⬚C

A

2

120– 160

8.60

1 1 1 1 1 1 1

C

2 616 4 213.0 3 068.8 1 603.0 1 121.4 1 879.81 970.87 1 380

202.0 225.0 215.0 250.0 179.0 112.0 178

6.857 26 6.881 7.258 7.676

1 138.92 645.9 1 133.4 1 559.1

228.88

9 688.7

0– 53 ⫺160 to ⫺112 ⫺115 to ⫺14.6 ⫺70 to 52

2

1255– 1442

8.179

2 2 2 2 2 2 2

180– 883 976– 1155 1156– 1430 800– 1360 1562– 1701 1063– 1307 1010– 1402

7.553 8.329 7 8.548 7.472 8.640 8.371 7.030

2

940– 1140

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

B

7.631 6 10.250 9 7.888 7 8.385 4 6.577 81 6.257 3 7.420

1 2 2 2

16.056 6.843 59 7.177 8.454 6.783 6 6.684 6.839 5 8.416 0 7.067 6 9.754 3 7.282 28 10.565 7 11.590 1 14.255 9 9.050 85 7.056 7.287 45 7.173 1 6.959 06 7.071 8 6.874 7.019 7.015 6 6.881 6.885

top of rh base of rh

5 395.4 9 417.07 9 704.3 8 122.81 11 396.6 8 623.2 6 894 18 802.8 2 500.12 1 660 1 594 1 341 628 823.4 1 096.5 1 100.6 1 553.8 999.900 2 273.8 2 665.6 3 692.1 1 735.31 1 445 1 446.7 1 100.1 775.48 840.3 1 110 1 460 1 257.4 1 120 1 140

186.30 185 227 206.0 256 248.0 262.0 234.0 225.0 237.190 255.0 264.0 273.0 236.50 206 252.7 244.00 234.00 249.0 229 202 204.0 229 227

short standard long

DEAN #37261

LEFT

(McGHP)

5.38

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.8 Vapor Pressures of Various Inorganic Compounds (Continued) Substance Sulfur (continued) SO2BrF SO2Cl2 SO2ClF SO2F2 Tantalum TaBr5 TaCl5 TaF5 TaI5 Technetium TcF6 TcO3F Tc2O7 Tellurium Te TeCl4 TeF6 Te2F10 TeO2 Thallium Tl TlF Thorium ThF4 ThH2 Tin SnCl4 SnH4 Titanium TiCl2 TiCl3 TiCl4 TiI4 Tungsten W Uranium UF6 UH3 dissociation U2H3 (UD3) U3H3 (UT3) Vanadium VBr2 VBr3 VCl2 VCl3 VCl4 VF3 VF5

State

Eq.

liq liq liq liq

1 1 1 1

liq liq liq liq

2 2 2 2

liq liq c liq

3 2 2 2

liq liq liq liq

1 1 1 1 2

Range, ⬚C

A

B

7.142 8 7.001 7 6.521 5 6.907 0

1 155 1 209 793.73 784.3

8.11 8.68 8.524 7.67

3 260 2 970 2 834 3 950

24.808 7 8.417 18.279 8.999

2 405 2 065 7 205 3 571

450– 733

7.301 0 7.558 6 6.748 8 6.901 8 12.328 4

5 370.6 2 355 807.0 1 150 13 222

2 2

950– 1200 282– 298

6.1240 12.52

6 268 5 484

2 2

up to 883

10.821 9.50

15 270 7 650

2 2

⫺52 to ⫺38 ⫺148 to ⫺49

9.824 7.400

2 2 2 2

455– 550 ⫺23 to 136 160– 360

9.30 10.401 7.683 7.577

8 500 8 296 1 964 3 054

2

2230– 2770

9.920

46 850

liq liq

1 1 2 2 2

64– 116 116– 230 200– 430

c subl c

2 2 2 2 2 2 2 2 2

541– 716 800– 905 314– 427 910– 1100 352– 567 30– 153 650– 920 ⫺20 to 19.5 19.5– 45.5

liq

subl c subl c liq liq

subl c liq subl c subl c liq

220– 240

37.4– 51.7 18.3– 51.8

6.994 64 7.690 69 9.39 9.43 9.46 9.08 5.9 11.12 5.725 11.20 7.62 12.357 8.168 7.549

C

231.0 224.0 210.70 250

5.803 6

221 115 247.0 227.0

2 441.23 999.68

1 126.288 1 683.165 4 590 4 500 4 471 10 460 9 830 7 470 9 721 9 777 2 020 15 603 2 608 2 423

221.963 302.148

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.39

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.8 Vapor Pressures of Various Inorganic Compounds (Continued) Substance Vanadium (continued) VI2 VOCl3 Xenon Xe XeF2 XeF4 Zinc Zn

State

Eq.

Range, ⬚C

A

subl c liq

2 2

850– 1016 15.4– 125

2.56 7.69

c liq subl c subl c

1 1 1 1

c

2

B

C

5 600 1 920

7.484 5 6.642 89 10.019 47 10.913 87 250– 419

top of rh base of rh

9.200

714.896 566.282 2 683.96 3 095.06

264.0 258.660 261.68 269.56

6 946.6

TABLE 5.9 Vapor Pressures of Various Organic Compounds Substance Acenaphthene Acetaldehyde Acetic acid Acetic anhydride Acetone Acetonitrile Acetophenone Acetyl bromide Acetyl chloride Acetylene Acetyl iodide Acrylic acid Acrylonitrile Allyl isothiocyanate m-Aminobenzotrifluoride p-Aminophenol Aniline Anthracene 9,10-Anthracenedione Benzene Benzenethiol Benzoic acid Benzonitrile Benzophenone Benzotrifluoride Benzoyl chloride Benzyl acetate Benzyl alcohol

Eq.

Range, ⬚C

1 2 1 1 1 1 1 2 1 1 1 1 1 1 1 1 1

147– 187 147– 288 liq liq liq liq liq 30– 100 liq liq ⫺130 to ⫺83 ⫺82 to ⫺72 liq 20– 70 ⫺20 to 140 10– 50 0– 96 96– 300 130– 185 102– 185 100– 160 176– 380 224– 286 285– 370 ⫺12 to 3 8– 103 52– 198 60– 110 liq 48– 202 200– 306 ⫺20 to 180 140– 200 46– 156 122– 205

1 1 2 1 2 2 1 1 1 2 1 1 1 1 2 1 1

A 7.728 8.033 8.005 7.387 7.149 7.117 7.119 9.135 5.197 6.948 9.140 7.099 4.181 8.538 7.038 5.126 7.651 7.170 ⫺3.357 7.320 8.91 7.674 12.305 8.002 9.106 6.905 6.990 9.033 6.746 7.349 7.162 7.007 7.924 8.457 7.198

B 19 52 82 48 14 88 2 02 87 2 9 44 67 55 58 86 30 50 10 01

4 65 19 31 66 94 08 5 05 17

2 2 1 1 1 1 1 2

534.234 834.99 600.017 533.313 444.718 210.595 314.4 878.8 545.784 1 115.954 1 232.6 711.0 355.452 2305.843 1 232.53 791.434 1 940.6 1 650.21 699.157 1 731.515 3 761 2 819.63 5 747.9 3 341.94 1 885.9 1 211.033 1 529.454 3 333.3 1 436.72 2 331.4 2 051.855 1 331.30 2 372.1 2 623.206 1 632.593

C 245.576 291.809 222.309 199.817 229.664 230 150.396 223.554 280.9 253.4 108.160 266.547 222.47 154.019 218.0 193.58 ⫺331.343 206.049 247.02

244.2 220.790 203.048 181.0 195.0 173.074 220.58 259.067 172.790

short standard long

DEAN #37261

LEFT

(McGHP)

5.40

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance Biphenyl 2-(2-Biphenylyloxy)ethanol Bromobenzene 2-Bromobenzyl cyanide 1-Bromobutane Bromochloromethane Bromochlorodifluoromethane 2-Bromo-2-chloro-1,1,1-trifluoroethane Bromocyclohexane p-Bromodiphenyl ether Bromoethane Bromoethene 2-Bromoethylbenzene 4-Bromoethylbenzene 2-Bromo-2-methylpropane 1-Bromonaphthalene o-Bromostyrene p-Bromostyrene 4-Bromotoluene 2-Bromovinylbenzene 4-Bromovinylbenzene 1,2-Butadiene 1,3-Butadiene n-Butane 1-Butanethiol 2-Butanethiol 1-Butanol 2-Butanol 2-Butanone 1-Butene 2-Butene cis trans Butyl acetate n-Butylamine trimethylboron n-Butylbenzene sec-Butylbenzene t-Butylbenzene n-Butyl borate n-Butyl-t-butyl ether Butyl carbitol Butyl cellosolve sec-Butyl chloroacetate n-Butylcyclohexane sec-Butylcyclohexane t-Butylcyclohexane n-Butylcyclopentane n-Butyl formate sec-Butyl formate n-Butyl-␣-hydroxyisobutyrate

Eq.

Range, ⬚C

A

1 1 1 1 1 1 1 1

69– 271 240– 300 56– 154 85– 152 ⫺78 to 23 16– 68 ⫺95 to 10 ⫺51 to 55

7.245 8.005 6.860 5.044 5.281 6.496 6.839 6.945

41 87 64 59 38 06 98 02

1 998.725 2 776.761 1 438.817 734.821 685.001 942.267 935.632 1 127.856

6.979 7.009 6.681 6.988 6.997 7.800 6.982 7.395 7.003 6.910 7.228 7.007 0.564 12.504 7.398 6.993 7.035 6.849 6.808 6.927 6.886 7.476 7.474 7.063 6.792 6.884 6.883 7.127 8.465 6.983 6.942 6.922 7.406 6.955 7.741 6.956 7.933 6.910 6.890 6.856 6.899 7.693 6.493 8.421

80 3 43 6 4

1 1 1 1 1 2 1 1 1 1 1 1

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

68– 260 25– 190 190– 400 28– 75 ⫺88 to 16 127– 217 liq 0– 72.8 liq liq 85– 280 110– 129 119– 147 ⫺69 to ⫺34 ⫺26 to 30 ⫺80 to ⫺62 ⫺58 to 15 ⫺77 to 19 ⫺2 to 123 ⫺13 to 110 15– 131 25– 120 43– 88 ⫺82 to 13 ⫺73 to 23 ⫺76 to 20 60– 126 0– 99 62– 213 87– 174 84– 170 117– 218 83– 124 50– 153 93– 170 30– 172 60– 211 91– 180 84– 173 41– 185 29– 112 30– 100 112– 185

B

09 9 50 38 38 62 97 2 22 83 55 99 96 54 98 80 31 56 90 68 37 12 21 17 19 55 87 56 14 59 38 30 96 80 35 6 7

7 1 1

1 1 1 1 1

1 1 1 1 1 1 1 2 1 2 1 1 1 1 1 2

572.19 902.7 683.84 121.9 009.9 235.4 632.60 512.7 927.05 631.2 743.67 612.35 82.913 349.00 219.877 041.117 998.106 930.546 935.86 281.018 229.904 362.39 314.19 261.34 908.80 967.32 967.50 430.418 980.98 577.965 533.95 505.987 905.035 348.702 056.904 399.903 103.30 538.518 530.70 501.724 457.08 698.7 972.9 617.32

C 202.733 206.914 205.441 59.273 160.880 192.587 240.330 227.341 217.38 153.3 132.90 234.7 251.6 238.7 193 262.2 186.0 195 218.0 206.36 ⫺191.71 559.02 259.776 242.274 245.233 238.854 238.73 218.100 222.021 178.77 186.55 221.97 238.54 237.87 240.84 210.745 193.60 201.378 204.39 203.490 186.134 206.303 195.655 172.154 249.29 200.833 202.373 206.108 205.99 247.4 176.0 287.09

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.41

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance 1-n-Butylnaphthalene 2-n-Butylnaphthalene n-Butyl nitrate 1-Butyl pentafluoropropionate 2-sec-Butylphenol 2-t-Butylphenol 4-t-Butylphenol Butyl phenyl ether n-Butyl propionate n-Butyl trifluoroacetate 1-Butyl trimethylsilyl ether 1-Butyne 2-Butyne n-Butyraldehyde Butyric acid Camphor Capric acid Caproic acid Capronitrile Caprylic acid Carbazole Carbitol Chloroacetic acid 4-Chloroacetophenone Chloroacetyl chloride N-Chloroaniline 2-Chloroaniline 3-Chloroaniline o-Chloroanisole Chlorobenzene o-Chlorobenzotrichloride 1-Chloro-4-bromobenzene 1-Chlorobutane 2-Chlorobutane 1-Chlorodecane 1-Chlorododecane Chloroethane 2-Chloroethylbenzene 3-Chloroethylbenzene 4-Chloroethylbenzene Chloroethylene Chloroform 1-Chloroheptane 1-Chlorohexadecane 1-Chlorohexane Chlorohexylisocyanate

Eq.

Range, ⬚C

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2 1 1 1 1 1 1 1 1 1 1 1 1 1 1

25– 170 170– 345 25– 170 170– 345 0– 70 82– 116 179– 240 135– 225 198– 252 119– 210 32– 93 71– 104 71– 124 ⫺68 to 27 ⫺51 to ⫺34 ⫺31 to 47 31– 74 90– 163 0– 180 178– 232 153– 187 98– 179 92– 164 130– 206 253– 358 40– 151 104– 190 122– 212 28– 107 61– 125 20– 108 108– 300 15– 125 125– 310 115– 186 62– 131.7 30– 150 150– 350 23– 63 ⫺17 to 78.6 0– 40 86– 225.9 116– 246 ⫺56 to 12.2

⫺65 to ⫺13 ⫺35 to 61 34– 160 166– 327 15– 136 90– 180

A 7.434 7.081 7.438 7.084 8.054 6.651 6.951 7.217 7.000 7.299 9.484 8.567 7.763 6.981 7.037 7.073 6.385 7.739 8.799 6.106 6.255 6.924 7.123 7.770 7.086 7.640 7.550 7.084 7.149 3.037 7.562 7.192 7.559 7.236 7.121 6.978 7.504 7.117 11.629 6.836 6.799 6.939 6.834 6.986 6.981 6.990 6.983 6.891 6.493 6.916 7.282 7.051 7.740

top of rh base of rh

B 47 4 08 8 27 00 93 56 38 7 89 94 00 98 91 38 44 9

3 9 1 64 3 81 16 57 77 67 65 40 39 03 36 08 30 94 94 23 86 08 47 69 82 09 17 4 70 03 36 95

2 1 2 1 1 1 1 1 1 1 2 2 1

1 1 2 1 1 1 1 1 2 1 1 1 1 1 1 2 1 1 1 2 1 3 1 1 1 1 1 1 1 1

1 2 1 2

227.7 971.5 242.2 984.3 992.83 108.02 593.74 822.81 627.51 882.70 852.58 305.22 884.68 988.75 896.91 101.71 913.59 764.7 797.39 043.6 106.3 340.8 597.2 933.05 179.4 801.31 723.365 693.63 340.79 171.35 998.6 762.74 073.75 857.75 655.80 431.05 228.07 951.37 643.30 173.79 149.12 639.06 654.82 030.01 556.0 577.3 577.0 905.01 929.44 453.96 152.61 461.72 340.50

C 202.2 180 202.3 180 254.30 177.04 163.79 196.23 155.24 215.82 296.98 301.06 261.31 233.01 199.06 235.81 185.48 199.9 116.4 57.96 126.6 212.8 159.36 163.5 183.97 179.98 190.95 208.70 ⫺14.99 220.0 200.0 215 196.64 188.77 217.55 220.0 196.27 218.13 224.68 177.94 155.09 238.61 201.0 200 200 239.48 196.03 199.83 162.73 215.57 241.90

short standard long

DEAN #37261

LEFT

(McGHP)

5.42

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance Chloromethane Chloromethoxytrichlorosilane 2-Chloro-2-methylpropane 1-Chlorononane 1-Chlorooctane Chloropentafluorobenzene p-Chlorophenetole 2-Chlorophenol ␤-Chloro-␤-phenylethyl alcohol 1-Chlorophenylisocyanate m-Chlorophenylisocyanate Chloroprene 1-Chloropropane 2-Chloropropane 3-Chloro-1-propene 2-Chloropropionitrile

␥-Chloropropyltrichlorosilane 1-Chlorotetradecane o-Chlorotoluene 1-Chloro-2,4,6-trinitrobenzene 1-Chloroundecane o-Chlorovinylbenzene p-Chlorovinylbenzene 2-Chlorovinyldichloroarsine cis trans 3-Chlorovinyldichloroarsine o-Cresol m-Cresol p-Cresol Cyanic acid Cyclobutane Cyclobutanone Cyclobutene Cycloheptane 1,3,5-Cycloheptatriene Cyclohexane Cyclohexanethiol Cyclohexanol Cyclohexene Cyclohexyl acetate Cyclohexylamine 1-Cyclohexylamino-2-propanol Cyclohexylpentafluoropropionate Cyclohexyltrifluoroacetate Cyclohexyltrimethylsilyl ether Cyclooctane 1,3,5,7-Cyclooctatetraene Cyclopentane Cyclopentanethiol Cyclopentanone Cyclopentene

Eq.

Range, ⬚C

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

⫺75 to ⫺5 0– 50 22– 47 69– 205 54– 184 36– 140 122– 212 80– 200 166– 259 50– 160 71– 158 20– 60 ⫺25 to 47 0– 30 13– 44 0– 84 84– 240 87– 179 142– 296.8 0– 65 65– 220 200– 270 101– 245 98– 155 100– 127 68– 109 50– 150 66– 110 120– 191 150– 201 128– 202 ⫺76 to ⫺6 ⫺60 to 12 ⫺24 to 25 ⫺77 to 2 68– 159 0– 65 20– 81 84– 203 94– 161 95– 172 61– 128 150– 238 82– 155 72– 147 91– 168 97– 194 0– 75 ⫺40 to 72 81– 173 0– 26

A 7.093 7.312 4.896 7.046 7.051 7.068 7.084 6.877 6.917 12.265 6.797 6.161 6.926 7.771 5.297 7.329 7.200 7.156 7.200 7.367 6.947 3.080 6.967 6.956 9.969 5.487 6.814 2.810 6.911 7.508 7.035 7.568 6.916 6.116 7.305 6.853 6.974 6.841 6.886 6.255 6.886 7.975 6.689 7.011 7.725 7.802 8.090 6.861 7.006 6.886 6.914 2.902 6.920

49 92 54 52 83 57 31 33 9 29 50 48 16 73 85 4 7 97 63 9 6 6 1 9 0 5 7 0 08 59 31 68 7 95 33 30 73 3 17 86 54 56 5 35 52 87 69 76 97 47 66

B

C

948.58 1 545.71 334.99 1 655.57 1 600.24 1 389.19 1 693.63 1 471.61 1 635.63 6 532.55 1 512.43 783.45 1 110.19 1 582 418.375 1 732.55 1 657.25 1 679.07 2 018.9 1 735.8 1 497.2 184.93 1 709.4 1 602.2 4 093.5 785.09 1 465.07 97.17 1 435.50 1 856.36 1 511.08 1 251.86 1 054.54 933.95 1 166.0 1 331.57 1 376.84 1 201.53 1 476.70 912.87 1 229.973 2 167.99 1 229.42 1 655.02 1 844.73 1 954.66 2 276.62 1 437.79 1 472.11 1 124.162 1 388.63 162.90 1 121.818

249.34 226.10 114.0 192.26 200.28 213.75 190.95 193.17 145.87 499.59 180.90 179.7 227.94 288 128.168 211.79 205.3 210.38 170.6 230.0 209.0 ⫺117.9 172.9 204.5 392.4 115.61 178.53 ⫺27.51 165.16 199.07 161.85 243.79 241.37 183.19 261.06 216.35 220.75 222.65 209.83 109.13 224.10 252.30 188.80 162.59 224.89 249.33 267.94 210.02 215.84 231.36 212.05 63.22 223.45

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.43

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance Cyclopentyl-1-thiaethane Cyclopropane o-Cymene m-Cymene p-Cymene Decahydronaphthalene cis trans Decane 1-Decanethiol 1-Decanol 1-Decene Decylbenzene Decylcyclohexane Decylcyclopentane Deuterodiborane Diacetone alcohol 1,3-Diacetylbenzene 1,4-Diacetylbenzene Diacetylene Diallyl sulfide 4,4⬘-Diaminodiphenylmethane Diamyl ether Dibenzyl ketone 1,2-Dibromobenzene Dibromodichloroethane Dibromodifluoromethane 1,2-Dibromoethane 1,2-Dibromoethylene cis trans 1,2-Dibromopropane 1,3-Dibromopropane Di-n-butyl ether Di-t-butyl ether Di-n-butyl phthalate Di-n-butyl sebacate Di-n-butyl sulfide 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene Dichlorobenzotrichloride Dichlorobenzyl chloride 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene 1,2-Dichloroethylene cis trans 2,2⬘-Dichloroethyl sulfide

Eq.

Range, ⬚C

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

83– 199 ⫺90 to ⫺32 81– 180 79– 176 107– 178 68– 228 61– 219 58– 203 109– 271 25– 52 103– 230 54– 199 203– 298 197– 298 182– 279 ⫺155 to ⫺94 28– 115 50– 145 116– 157 ⫺78 to 0 10– 40 198– 272 105– 187 285– 325 20– 117 117– 300 25– 130 ⫺26 to 23 52– 131 26– 78 4– 71 0– 50 50– 250 0– 71 71– 275 89– 140 4– 109 126– 202 128– 208 10– 40 131– 181 91– 173 95– 174 20– 167 167– 340 20– 138 138– 350 ⫺39 to 18 ⫺31 to 99 ⫺28 to 32 0– 84 ⫺38 to 85 15– 76

A 6.940 6.887 7.266 7.123 7.050 6.875 6.856 6.943 6.998 11.560 6.922 6.934 7.035 7.019 6.999 6.480 8.502 0.056 2.803 4.990 4.829 3.172 7.067 8.257 7.501 7.102 5.197 7.152 6.721 7.038 4.581 7.303 6.891 7.549 7.198 6.796 6.932 6.639 7.587 6.769 7.143 7.040 7.020 7.439 6.985 7.504 7.147 6.977 7.025 6.972 7.022 6.965 8.587

top of rh base of rh

83 88 10 74 74 29 81 65 1 44 77 96 37 12 83 42 24 71 79 30 31 10 28 65 53 22 48 74 11 98 05 84 74 3 9 80 66 3 78 1 8 54 24 57 35 0 3 2 3 1 41

B

C

1 480.70 856.01 1 768.45 1 644.95 1 608.91 1 594.460 1 564.683 1 495.17 1 713.6 4 055 1 472.01 1 484.98 1 903.98 1 899.33 1 822.05 545.20 2 400.56 64.188 177.25 356.36 643.18 210.49 1 604.77 3 244.42 2 093.7 1 825.77 763.44 1 181.612 1 280.82 1 349.84 393.641 1 644.4 1 419.60 1 890.56 1 678.26 1 297.29 1 348.53 1 744.20 2 364.89 1 208.80 1 704.49 1 607.05 1 590.9 2 190.0 1 868.91 2 125.9 1 881.38 1 174.02 1 271.3 1 099.4 1 205.4 1 141.9 2 588.23

208.47 246.50 224.95 212.76 208.72 203.39 206.26 193.86 177.0 273.2 133.98 195.707 160.33 161.35 163.05 244.73 263.79 ⫺196.97 ⫺46.43 143.22 142.34 ⫺137.41 196.58 230 207.0 110.81 253.85 201.75 209.26 103.56 232.0 212.0 240.0 222.0 191.03 233.79 113.69 147.54 217.51 219.42 213.38 210.2 200 172.00 213.8 192.93 229.06 222.9 237.2 230.6 231.9 246.06

short standard long

DEAN #37261

LEFT

(McGHP)

5.44

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance 1,2-Dichloroethyltrichlorosilane Dichloromethane 2-(2,4-Dichlorophenoxy)-ethanol 3,4-Dichlorophenylisocyanate 1,2-Dichloropropane 3,4-Dichlorotoluene Diethanolamine 1,1-Diethoxyethane Diethoxymethane Diethylaluminum chloride Diethylamine N,N-Diethylaniline 1,2-Diethylbenzene 1,3-Diethylbenzene 1,4-Diethylbenzene Diethyldichlorosilane Diethyl disulfide Diethylene glycol Diethyl ether Diethyl ethylphosphate N,N-Diethylformamide Diethyl ketone 3,3-Diethylpentane 3,5-Diethylphenol Diethylpropylphosphonate Diethyl sulfide 1,2-bis-Difluoroamino-4-methylpentane Difluoromethane 1,2-Dihydroxybenzene 1,3-Dihydroxybenzene 1,2-Diiodoethylene cis trans Diisoamyl sulfide p-Diisopropylbenzene Diisopropyl ether 2,4-Diisopropylphenol 1,2-Dimethoxyethane N,N-Dimethylacetamide Dimethylamine bis-Dimethylaminoborane N-Dimethylaminodiborane bis-Dimethylaminodifluorosilane N,N-Dimethylaniline Dimethyl beryllium 1,4-Dimethyl-bicyclo(2,2,1)heptane 2,3-Dimethyl-bicyclo(2,2,1)heptane trans 2,3-Dimethyl-1,3-butadiene 2,2-Dimethylbutane

Eq.

Range, ⬚C

A

102– 181 ⫺40 to 40 212– 286 60– 190 45– 96 0– 105 105– 330 194– 241 0– 70 0– 75 44– 125 31– 61 50– 218 liq liq liq 48– 128 15– 61 61– 230 130– 243 ⫺61 to 20 76– 134 30– 90

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

⫺82 to ⫺32 118– 246 151– 276 29– 152 77– 130 10– 80 120– 211 23– 67 122– 255 0– 60 30– 90 ⫺72 to 6.9 ⫺25 to 62.5 ⫺38 to 14 24– 88 71– 197 100– 180 56– 119

1

72– 138

6.868 15

1 420.32

212.94

1 1

0– 68.5 ⫺42 to 73

7.119 7 6.754 83

1 299.69 1 081.176

238.09 229.34

7.138 7.577 7.889 5.522 6.093 ⫺1.959 6.993 6.849 6.714 6.718 9.720 7.082 5.584 8.340 5.952 7.367 19.089 6.761

2 09 3 7 94 25 8 63 41 70 6 0 80 60 20 9 89 07 7 32 6 4 91 03 3 1 36 11 9

1 8 3 5 9 9 12 52 1 7 9 96

2 1 2 3 1 1 1 2 1 1 2

C

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

63– 147 114– 248 87– 134 0– 150 ⫺20 to 20

7.826 7.409 7.240 8.679 6.980 7.343 6.979 8.138 6.757 6.908 8.229 5.801 7.466 6.987 7.003 6.998 6.862 7.349 6.975 7.636 6.920 4.101 6.395 6.857 6.896 7.651 4.558 6.928 8.009

B 144.9 325.9 004.31 312.3 308.1 882.5 655.44 327.9 191.60 229.52 484.53 583.30 993.57 576.940 575.310 588.310 346.3 695.00 485.970 939.4 064.07 315.17 203.8 216.3 453.48 228 446.50 257.83 944.92

253.1 252.6 157.25 333.9 222.8 215.0 195.0 174.4 203.12 217.01 255.45 144.1 218.5 200.51 200.96 201.97 207.7 227.29 208.96 162.7 228.80 15.50 165.6 204 215.83 218.5 26.17 218.66 245.44

821.7 2 054 2 231 797.8 1 197.0 390.61 1 663.88 1 139.34 1 506 1 050.5 3 273.8 960.242 774.371 1 917.35 748.7 1 857.08 11 535.45 1 342.66

244.7 187 169 106.4 172.3 ⫺219.33 194.41 218.7 138 209.2 334.5 221.67 170.64 302.73 146.9 220.36 496.64 213.53

1 1 1 1 1 1 1 1 1 1 1 1 2 1 1

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.45

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance 2,3-Dimethylbutane 2,3-Dimethyl-2-butanethiol 2,3-Dimethyl-1-butene 2,3-Dimethyl-2-butene 3,3-Dimethyl-1-butene Dimethyl cadmium 1,1-Dimethylcyclohexane 1,2-Dimethylcyclohexane cis trans 1,3-Dimethylcyclohexane cis trans 1,4-Dimethylcyclohexane cis trans 1,1-Dimethylcyclopentane 1,2-Dimethylcyclopentane cis trans 1,3-Dimethylcyclopentane cis trans Dimethyldichlorosilane 1,2-Dimethyldisilane Dimethyl ether N,N-Dimethylformamide 2,2-Dimethylhexane 2,3-Dimethylhexane 2,4-Dimethylhexane 2,5-Dimethylhexane 3,3-Dimethylhexane 3,4-Dimethylhexane 1,1-Dimethylhydrazine 1,2-Dimethylhydrazine N,N-Dimethylhydroxylamine O,N-Dimethylhydroxylamine Dimethylmalononitrile 1,3-Dimethylnaphthalene 1,4-Dimethylnaphthalene (same for 1,6- and 1,7-) 1,8-Dimethylnaphthalene 2,3-Dimethylnaphthalene 2,6-Dimethylnaphthalene 2,7-Dimethylnaphthalene 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane 2,4-Dimethyl-3-pentanone Dimethyl-o-phthalate 2,2-Dimethylpropane 2,2-Dimethyl-1-propanol

Eq.

Range, ⬚C

A

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

⫺35 to 81 56– 167 ⫺36 to 78 ⫺21 to 97 ⫺47 to 64 ⫺2 to 23 10– 147 18– 158 13– 151 11– 147 15– 152 15– 152 10– 147 ⫺12 to 113 ⫺3 to 125 ⫺9 to 117 ⫺10– 116 ⫺9 to 117 28– 72 ⫺46 to 0 ⫺71 to ⫺25 30– 90

6.809 6.839 6.862 6.950 6.677 6.490 6.798 6.837 6.833 6.838 6.834 6.832 6.817 6.817 6.850 6.844 6.837 6.838 7.062 4.024 6.976 6.928 6.837 6.870 6.853 6.859 6.851 6.879 7.408 5.611 7.565 7.405 7.035 7.634 7.269 7.634 7.269 7.407 7.056 7.403 7.052 7.396 7.046 7.398 7.047 6.814 6.853 6.826 6.826 6.968 4.522 6.604 7.875

⫺35 to 20 1– 25 17– 90 ⫺45 to 42.2 49– 140 20– 148 148– 310 20– 148 148– 310 25– 150 150– 320 20– 155 155– 315 20– 150 150– 310 25– 150 150– 310 ⫺19 to 103 ⫺10 to 115 ⫺17 to 105 ⫺14 to 112 48– 125 82– 151 ⫺14 to 29 55– 115

top of rh base of rh

B 83 56 36 58 51 55 21 46 08 83 55 87 73 24 08 22 15 17 1 3 03 0 15 04 05 84 21 86 13 9 8 4 5 7 8 7 8 89 4 96 7 8 0 75 8 80 82 21 67 53 32 27 3

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

1 1 1 1 1 1 1 1 1 1 1 2 2 2 2 2 1 2 1 2 1 2 1 1 1 1 1 1

1

127.187 354.24 134.675 215.428 010.516 126.36 321.705 367.311 353.881 338.473 343.687 345.613 330.437 219.474 269.140 242.748 237.456 240.023 280.29 255.4 889.264 400.87 273.59 315.50 287.88 287.27 307.88 330.04 305.91 633.59 415.96 245.58 546.99 295.4 076.0 345.8 076.0 123.2 879 111.9 869 080.3 841 085.9 846 190.033 238.017 192.04 228.663 382.84 700.31 883.42 604.7

C 228.90 215.96 229.37 225.44 224.91 201.07 217.85 215.84 219.13 218.07 215.39 216.15 218.58 221.95 220.21 221.69 222.01 221.62 235.65 129.2 241.96 196.43 215.07 214.16 214.79 214.41 217.44 214.86 225.53 143.17 201.93 233.06 202.00 232.4 210 232.6 210 201.2 180 201.1 180 200.8 180 200.9 180 223.30 221.82 225.32 225.32 213.06 51.42 227.78 208.2

short standard long

DEAN #37261

LEFT

(McGHP)

5.46

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance 2,5-Dimethylpyrrole 2,4-Dimethylquinoline 2,6-Dimethylquinoline Dimethyl sulfide 3,3-Dimethyl-2-thiabutane 2,2-Dimethyl-3-thiapentane 2,4-Dimethyl-3-thiapentane 2,3-Dimethylthiophene 2,4-Dimethylthiophene 2,5-Dimethylthiophene 3,4-Dimethylthiophene 1,3-Dinitrobenzene 2,4-Dinitrotoluene 2,6-Dinitrotoluene 3,5-Dinitrotoluene 1,4-Dioxane Dipentene 2,2⬘-Diphenol Diphenyldichlorosilane Diphenyl ether Diphenylmethane Di-n-propyl ether Disilanyl chloride 2,3-Dithiabutane 5,6-Dithiadecane 3,4-Dithiahexane 4,5-Dithiaoctane Dodecane 1-Dodecanethiol Dodecanoic acid 1-Dodecanol 1-Dodecene Durenol Eicosane 1-Eicosanethiol 1-Eicosene Ethane Ethanethiol Ethanol Ethanolamine Ethyl acetate m-Ethylacetophenone p-Ethylacetophenone Ethylamine N-Ethylaniline Ethylbenzene 2-Ethyl-1-butene Ethyl butyl ether Ethyl chloroacetate p-Ethylchlorobenzene Ethylcyclohexane Ethylcyclopentane Ethylene

Eq. 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

Range, ⬚C 100– 199 185– 269 188– 267 ⫺22 to 20 liq liq liq 50– 205 50– 205 47– 200 54– 205 252– 292 200– 299 150– 260 220– 270 20– 105 21– 170 171– 325 192– 281 204– 271 217– 282 26– 89 ⫺46 to 18 6– 135 101– 263 40– 182 72– 226 91– 247 106– 176 138– 214 89– 244 108– 249 198– 379 liq ⫺142 to ⫺75 ⫺49 to 56 ⫺2 to 100 65– 171 15– 76 19– 143 21– 94 ⫺20 to 90 50– 207 26– 164 ⫺28 to 88 38– 92 25– 146 109– 184 20– 160 ⫺0.1 to 129 ⫺153 to ⫺91

A 7.203 7.025 6.931 7.150 6.847 6.850 6.871 6.924 6.993 6.961 6.996 4.337 5.798 4.372 1.556 7.431 7.111 8.193 6.999 7.011 6.291 6.947 7.104 6.977 6.963 6.975 6.975 6.997 7.024 7.860 7.539 6.976 7.758 7.152 7.114 7.135 6.829 6.952 8.321 7.456 7.101 3.767 4.274 7.054 7.422 6.957 6.997 6.944 6.967 6.951 6.867 6.887 6.744

B 06 4 12 9 09 86 18 9 9 1 1

1 1 1 1 1 1 1 1 1 1 1 1

55 6 5 03 04 6 8 92 8 07 29 95 4 8 86 07 2 1 15 06 09 8 79 2 6 13 8 19 12 4 1 28 09 19

1 1 3 1 1 1 1 1 1 1 1 1 1 1 2 2 1 2 2 2 2 1 1 1 1

1 1 1 1 1 1 1 1

509.60 830.29 748.73 195.58 259.648 323.24 327.12 430.0 450.7 427.7 467.1 229.2 118 380 30.59 554.68 613.42 067.6 918.20 799.71 261 256.5 211.8 346.342 684.1 485.970 603.793 639.27 817.8 159.1 003.29 621.11 432 032.7 125 043.0 663.72 084.531 718.10 577.67 244.95 708.05 629.34 987.31 903.4 424.255 218.352 256.4 355.9 557.1 382.466 298.599 594.99

C 181.76 174.44 166.37 242.68 218.69 212.89 212.55 212 212.0 213.2 211.5 ⫺137 61.8 ⫺43.6 ⫺302 240.34 207.8 253.1 161.41 177.74 105 219.0 245.2 218.86 181.3 208.96 195.85 181.84 164.1 143.2 168.13 182.45 250 132.1 119 137.9 256.68 231.39 237.52 173.37 217.88 182.6 120.9 220.0 214.3 213.21 231.30 216.9 188.2 198.1 214.99 220.68 256.16

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.47

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance

Eq.

Ethylene glycol Ethylene glycol monoethyl ether Ethylene glycol monomethyl ether Ethylene oxide Ethyl formate 3-Ethylhexane 2-Ethyl-1-hexanol 2-Ethyl-2-hexenal Ethyl iodoacetate Ethyl isothiocyanate Ethyl methyl ether Ethyl methyl ketone 3-Ethyl-5-methylphenol 2-Ethyl-4-methyl-1-pentanol Ethyl nitrate 3-Ethylpentane 2-Ethylphenol 3-Ethylphenol 4-Ethylphenol Ethyl phenyl ether Ethyl n-propanoate Ethyl n-propyl ether Ethyl n-propyl ketone m-Ethylstyrene p-Ethylstyrene Ethyl trichloroacetate Ethyl trichlorosilane Ethyl triexthoxysilane Ethyl vinyldichlorosilane Fenchyl alcohol Fluoranthene Fluorene Fluorobenzene m-Fluorobenzotrifluoride bis-(Fluorocarbonyl)-peroxide p-Fluorotoluene Formaldehyde Formic acid Formyl fluoride Furan 2-Furfuraldehyde Glycerol Glyceryl-1,3-diacetate Guaiacol Hemellitenol Heptadecane 1-Heptadecene Heptane 1-Heptanethiol Heptanoic acid 1-Heptanol 1-Heptene Hexadecane

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

Range, ⬚C 50– 200 63– 134 56– 124 ⫺49 to 12 4– 54 74– 184 54– 175 29– 89 10– 50 5– 7.7 195– 247 70– 176 0– 60 ⫺7 to 119 86– 208 97– 218 101– 218 117– 181 34– 98 20– 63 75– 133

44– 95 28– 96 64– 153 45– 122 59– 200 197– 384 161– 300 ⫺18 to 84 40– 137 ⫺47 to ⫺7 68– 155 ⫺109 to ⫺22 37– 101 ⫺95 to ⫺61 2– 61 56– 161 183– 260 100– 190 82– 205 123– 248 161– 337 ⫺2 to 124 58– 206 112– 150 60– 176 ⫺6 to 118 149– 321

A 8.090 8 7.874 6 7.849 8 7.128 43 7.009 0 6.890 98 6.914 7 6.861 3 4.073 7 7.106 0 5.518 6.974 21 7.040 83 6.582 6 7.163 7 6.875 64 7.800 3 7.468 8.291 7.021 38 6.994 9 6.985 1 7.000 82 7.039 28 6.900 71 7.725 4 6.606 6.886 8 6.859 5.693 6.373 7.761 8 7.187 0 7.006 59 9.608 4 6.994 26 7.195 8 7.581 8 5.270 6.975 27 6.575 9 6.165 6.407 3 6.161 6.972 7.014 3 7.008 67 6.896 77 6.952 49 5.287 4 6.647 67 6.901 87 7.028 67

top of rh base of rh

B 2 1 1 1 1 1 1 1 1 1 1 1 1 1 2 1 2 1 1 1 1 1 1 1 1 1 1 1 2 1 1 2 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

088.9 843.5 793.9 054.54 123.94 327.88 339.7 457.4 374.64 567.5 434.5 209.6 615.44 134.6 338.8 251.827 140.4 856 423 508.39 260.6 188.5 365.79 614.0 570.9 927.0 118 377.9 331 797.6 756 637.1 381.8 304.35 247.64 374.055 970.6 699.2 362 060.87 198.7 036 092.0 051 563 865.1 868.9 264.90 525.311 665.54 140.64 258.345 830.51

C 203.5 234.2 236.9 237.76 218.2 212.60 147.8 190.6 54.8 234.2 158 216 152.6 129.2 224.9 219.89 227 187 229 194.49 207.4 226.4 208.01 198 198 233.7 201 183.0 210.8 84.6 118 243.2 235.6 215.67 319.83 217.40 244.1 260.7 175 227.74 162.8 28 119.3 116 134 149.20 152.50 216.54 197.70 42.07 126.56 219.30 154.45

short standard long

DEAN #37261

LEFT

(McGHP)

5.48

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance 1-Hexadecanethiol 1-Hexadecanol 1-Hexadecene 1,5-Hexadiene Hexafluoroacetone Hexafluorobenzene Hexafluorodisiloxane Hexafluoroethane Hexahydroindane cis trans Hexamethyldisiloxane Hexane 1-Hexanethiol 1-Hexanol 2-Hexanol 3-Hexanol 1-Hexene 3-Hexyne Hydroquinone 3-Hydroxy-3-methyl-2-butanone Iodobenzene Iodoethane Isoamyl acetate Isobutylbenzene Isobutyl borate Isobutyl cellosolve Isobutylcyclohexane Isobutyl nitrate Isobutyraldehyde Isobutyric acid Isocaproic acid Isopropylbenzene Isopropyl borate o-Isopropylbromobenzene Isopropyl caprate Isopropyl caprylate Isopropyl cellosolve Isopropyl chloroacetate Isopropylcyclohexane Isopropylcyclopentane Isopropyl laurate Isopropyl myristate Isopropyl nitrate Isopropyl palmitate o-Isopropylphenol p-Isopropylphenol Isopropyl phenyl ether Isopropyl stearate Isopseudocumenol Isoquinoline Isovaleric acid Ketene

Eq. 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

Range, ⬚C

50– 103 145– 190 0– 59 ⫺79 to ⫺27 5– 114 ⫺39 to ⫺23 ⫺93 to ⫺78 77– 168 71– 161 36– 138 ⫺25 to 92 40– 181 35– 157 25– 142 25– 138 16– 64 ⫺20 to 24 159– 286 45– 146 20– 188 30– 60 41– 95 86– 174 99– 200 71– 159 85– 172 0– 70 13– 63 58– 152 96– 133 39– 181 65– 139 132– 210 90– 178 65– 146 67– 140 35– 153 71– 155 47– 127 117– 196 140– 193 0– 70 160– 197 97– 215 108– 228 72– 175 182– 207 106– 233 167– 244 86– 104 ⫺88 to ⫺49

A 7.075 7.281 6.158 7.040 6.574 6.650 7.032 7.471 6.793 6.868 6.861 6.773 6.876 6.946 7.860 7.261 7.689 6.857 5.895 8.137 7.340 7.011 6.959 7.436 6.935 7.197 7.694 6.867 8.164 6.735 4.894 6.258 6.936 8.070 6.717 9.959 8.032 7.500 8.382 6.873 6.887 8.532 10.418 7.266 10.916 8.167 8.666 6.517 0.079 5.602 6.912 3.946 7.615

B

7 6 11 1 2 95 2 35 22 19 79 01 64 45 0 70

9 9

56 8 97 3 1

66 8 2 0 14 36 6 0 6 4

6 3 2 55

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2 1 1 1 1 1 1 1 1 2 1 1 1 2 1 4 2 1 2 1 1 2 4 1 5 2 2 1

1 1

990 909.7 380.0 840.52 013.5 725.90 227.98 169.3 657.06 497.33 475.70 202.03 171.17 454.004 761.26 371.7 670.0 148.62 863.3 461 653.6 640.1 232 606.6 530.05 745.8 825.9 493.10 022.7 053.2 382.6 038.6 460.793 120 462.7 013.9 213.6 639.2 328 453.20 380.12 951.6 866.48 434.4 572.0 343 810 238.0 10.41 768 723.4 255.41 036

C 140 128.1 91 157.57 214.8 219.9 215.49 278.1 246.2 207.67 209.66 208.25 224.41 204.95 196.66 173.2 211.8 225.35 194 183 227.5 208.8 229 216 204.59 193 219.6 203.16 262.4 209.1 38 130 207.78 269 170.9 326.5 220.9 213.3 275 209.44 218.05 240.7 314.17 255.2 364.8 229 258 163.0 ⫺221 49 184.3 11.3 269

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.49

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance Lauric acid Lepidine 2,3-Lutidine 2,4-Lutidine 2,5-Lutidine 2,6-Lutidine 3,4-Lutidine 3,5-Lutidine Mesitol Mesityl oxide Methacrylonitrile Methane c liq Methanol Methoxybenzene N-Methylacetamide Methyl acetate Methylal Methylamine N-Methylaniline Methyl benzoate Methyl borate Methyl boric anhydride 2-Methyl-1,3-butadiene 3-Methyl-1,2-butadiene 2-Methylbutane 2-Methyl-1-butanethiol 3-Methyl-1-butanethiol 2-Methyl-2-butanethiol 2-Methyl-1-butanol 3-Methyl-1-butanol 2-Methyl-2-butanol 3-Methyl-2-butanol 2-Methyl-1-butene 3-Methyl-1-butene 2-Methyl-2-butene Methyl butyl ether 3-Methyl-1-butyne 2-Methyl-3-butyn-2-ol Methyl n-butyrate Methyl caprate Methyl caproate Methyl caprylate Methyl carbitol Methyl cellosolve acetate Methyl chloroacetate Methylcyclohexane Methylcyclopentane Methyldichlorosilane 1-Methyl-2-ethylbenzene

Eq.

Range, ⬚C

A

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

106– 176 199– 266 155– 162 150– 160 85– 157 79– 144 172– 180 163– 173 94– 221 14– 130

7.860 7.271 7.447 7.339 7.081 7.056 7.362 7.333 6.659 6.635 6.980 7.193 6.695 7.897 7.973 7.052 2.631 7.065 6.872 7.336 7.081 7.273 7.646 8.004 7.011 6.885 7.151 6.943 6.833 6.913 6.914 6.828 7.067 7.258 6.519 6.942 6.846 6.824 6.966 6.887 6.884 6.657 6.972 7.190 7.409 6.916 7.424 7.125 7.004 6.823 6.862 7.027 7.003

⫺195 to ⫺183 ⫺181 to ⫺152 ⫺14 to 65 64– 110 110– 164 40– 90 1– 56 0– 35 ⫺83 to ⫺6 50– 200 111– 199 31– 68 0– 55 ⫺52 to ⫺24 ⫺19 to 55 ⫺45 to ⫺20 ⫺20 to 62 ⫺57 to 49 liq liq liq 34– 129 25– 153 25– 102 25– 111 ⫺53 to 52 ⫺63 to 41 ⫺48 to 60 23– 69 ⫺55 to 47 21– 106 107– 188 44– 105 100– 146 112– 193 70– 144 45– 130 ⫺3 to 127 ⫺24 to 96 1– 41 48– 194

top of rh base of rh

B 8 2 8 0 0 7 0 1 8 2 09 61 50 28 69 1 2 2 9 9 0 1 87 64 95 50 15 85 91 37 30 21 3 1 37 55 59 1 80 5 11 0 3 5 1 4 00 83 8 14

2 1 1 1 1 1 1 1 1 1 1

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

159.1 946.14 832.6 733.4 539.6 470.2 840.1 783.6 392 186.1 274.96 451.64 405.42 474.08 515.14 489.99 121.7 157.63 049.2 011.5 631.3 847 491.5 726.1 126.159 071.578 194.537 103.901 040.73 347.317 342.509 254.885 195.26 314.36 863.4 090.9 039.69 012.37 124.33 162.1 014.81 976.5 272.73 783.8 672.74 496.3 751 447.0 306.3 270.763 186.059 167.8 535.374

C 143.2 177.64 240.1 230.4 209.6 208.0 231.5 228.7 148 186.0 220.7 268.49 267.78 229.13 232.85 203.57 ⫺9.3 219.73 220.6 233.3 192.4 221 245.5 257.9 238.88 233.51 239.47 230.89 235.45 215.07 214.45 218.76 156.83 169.36 135.3 157.2 236.65 236.65 236.63 219.9 227.11 154.1 208.5 181.6 218.98 176.5 192 196.1 187.3 221.42 226.04 240.7 207.30

short standard long

DEAN #37261

LEFT

(McGHP)

5.50

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance

Eq.

Range, ⬚C

1-Methyl-3-ethylbenzene 1-Methyl-4-ethylbenzene 1-Methyl-1-ethylcyclopentane 1-Methyl-2-ethylcyclopentane cis 2-Methyl-3-ethylpentane 3-Methyl-3-ethylpentane 3-Methyl-5-ethylphenol 2-Methyl-5-ethylpyridine N-Methylformamide Methyl formate 2-Methylheptane 3-Methylheptane 4-Methylheptane 2-Methylhexane 3-Methylhexane Methylhydrazine N-Methylhydroxylamine O-Methylhydroxylamine Methyl isobutyl ketone 1-Methyl-2-isopropylbenzene 1-Methyl-3-isopropylbenzene 1-Methyl-4-isopropylbenzene 3-Methylisoquinoline Methyl isothiocyanate Methyl laurate Methyl linolate Methyl methacrylate Methyl myristate 1-Methylnaphthalene 2-Methylnaphthalene Methyl oleate Methyl palmitate 2-Methylpentane 3-Methylpentane 2-Methyl-2-pentanethiol 2-Methyl-1-pentanol 2-Methyl-4-pentanol 2-Methyl-1-pentene 3-Methyl-1-pentene 4-Methyl-1-pentene 2-Methyl-2-pentene 3-Methyl-2-pentene cis trans 4-Methyl-2-pentene cis trans Methyl phenyl ether 2-Methylpiperidine 2-Methylpropane 2-Methyl-1-propanethiol 2-Methyl-2-propanethiol 2-Methyl-1-propanol 2-Methyl-2-propanol 2-Methylpropene

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

46– 190 46– 191 43– 122 49– 129

111– 233 52– 177 96– 200 21– 32 42– 119 43– 120 ⫺9 to 115 ⫺8 to 117 2– 25 40– 65 ⫺63 to 48 22– 116 liq liq liq 176– 225 10– 50 158– 212 166– 206 39– 89 166– 238 108– 278 105– 274 166– 205 148– 202 ⫺32 to 83 ⫺30 to 87 56– 165 25– 150 25– 133 ⫺30 to 85 ⫺38 to 77 ⫺38 to 77 ⫺26 to 90 ⫺26 to 91 ⫺23 to 94 ⫺35 to 79 ⫺33 to 81 110– 164 51– 158 ⫺87 to 7 ⫺10 to 113 1– 88 20– 115 26– 83 ⫺82 to 12

A 7.015 6.998 6.859 6.905 6.867 6.867 7.958 5.050 7.497 3.027 6.917 6.899 6.900 6.873 6.867 6.576 7.045 7.363 6.672 6.940 6.940 6.923 6.969 2.896 6.767 6.111 8.409 7.622 7.035 7.068 7.544 9.594 6.839 6.848 6.858 7.520 8.467 6.850 6.755 6.835 6.923 6.910 6.926 6.841 6.880 7.052 6.818 6.910 6.887 6.787 7.327 9.170 6.684

B 82 02 20 88 31 31

1 1 1 1 1 1 2

4

1

35 44 65 18 64 2 6 9 7 4 5 7 2 8 1 1 2 3 92 50 1 4 10 87 5 1 1 30 23 29 67 73 34 29 30 69 59 48 46 81 05 6 66

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2 2 1 1 2 4 1 1 1 1 2 1 1 1 1 1 1 1 1 1 1 1 1 1 2

529.184 527.113 347.602 388.412 318.12 347 236 517 849.4 3.02 337.47 331.53 327.66 236.026 240.196 007.5 223.3 225.3 168.4 548.05 539.05 537.06 717.3 103.6 589.72 660.1 050.5 283.93 826.948 840.268 656.9 146.43 135.410 152.368 343.79 564.7 174.9 138.516 086.316 121.302 183.837 186.402 194.527 120.707 142.874 489.99 274.61 946.35 237.282 115.565 248.48 206.4 866.25

C 208.51 208.92 217.21 216.89 215.31 219.68 208 59 201.1 ⫺11.9 213.69 212.41 212.57 219.55 219.22 181.4 172.1 225.2 191.9 203.15 203.93 203.05 166.9 45.4 140.5 118.8 274.4 184.8 195.00 198.40 200.7 297.76 226.57 227.13 212.8 189.2 257.8 224.70 226.20 229.687 225.51 226.70 224.83 226.59 227.14 203.57 205.40 246.68 220.31 221.31 172.92 267.9 234.64

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.51

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance N-Methylpropionamide Methyl propionate 2-Methyl-2-propylamine Methyl propyl ether 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 1-Methylpyrrole 6-Methylquinoline 7-Methylquinoline Methyl salicylate Methyl stearate o-Methylstyrene m-Methylstyrene p-Methylstyrene ␣-Methylstyrene ␤-Methylstyrene Methyl sulfoxide 3-Methyl-2-thiabutane 2-Methylthiacyclopentane 3-Methylthiacyclopentane 2-Methyl-3-thiapentane Methyl-2-thiazole 2-Methylthiophene 3-Methylthiophene Methyl trichlorosilane 2-Methyl-5-vinylpyridine Morpholine Naphthalene

c liq

1-Naphthol 2-Naphthol Nicotine o-Nitroaniline m-Nitroaniline p-Nitroaniline Nitrobenzene m-Nitrobenzotrifluoride Nitromethane 1-Nitropropane o-Nitrotoluene p-Nitrotoluene Nonadecane 1-Nonadecene Nonafluorocyclopentane Nonane 1-Nonanethiol Nonanoic acid 1-Nonanol

Eq.

Range, ⬚C

A

B

C

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2 2 2 1 1 1 1 1 1 1 1 1 1 1 1 1 1

30– 90 21– 79 19– 75 0– 39 80– 168 74– 185 75– 186 49– 149 187– 266 238– 258 79– 220 204– 240 32– 112 75– 255 10– 72 72– 250 68– 170

⫺0.9103 6.942 4 6.783 2 6.118 6 7.032 4 7.050 21 7.041 77 7.085 0 6.927 2 7.597 7 7.083 3 2.357 0 7.212 9 6.884 61 7.275 34 6.879 28 7.011 2 6.923 66 6.923 39 7.763 7 6.901 96 6.944 12 6.949 1 6.891 30 7.042 1 6.938 97 6.986 11 7.088 2 6.156 7.718 13 7.160 30 7.010 65 6.818 1 7.284 21 7.347 14 6.789 8.868 4 8.818 8 9.559 5 7.115 6 7.653 15 7.180 25 7.281 66 7.114 6 5.851 6.994 8 7.015 3 7.115 1 6.945 3 6.938 93 6.983 9 3.235 9 7.827 8

119.4 1 170.2 993.33 708.69 1 415.73 1 481.78 1 480.68 1 368.66 1 746.08 2 229.4 1 712.8 68.92 1 664.08 1 485.41 1 695.4 1 471.44 1 535.1 1 486.88 1 499.80 2 048.7 1 232.170 1 409.503 1 431.8 1 293.05 1 407.05 1 326.48 1 363.83 1 289.2 1 023 1 745.8 1 447.70 1 733.71 1 585.86 2 077.56 2 135.00 1 650 3 336.50 3 440.9 4 039.73 1 746.6 2 006.1 1 710.60 1 446.94 1 467.45 946 1 720.39 1 932.8 1 997.4 1 051.7 1 431.82 1 655.6 143.97 1 953.8

⫺148.0 208.8 210.50 179.9 211.63 211.25 210.50 212.80 166.46 214.9 187.1 ⫺156.5 214.59 200.0 220.0 200.0 200.7 202.4 201.0 231.6 221.67 214.41 213.6 215.04 209.33 214.31 216.78 239.9 129 235.0 210.0 201.86 184.82 184.0 183.0 176

20– 50 ⫺13 to 109 liq 67– 179 liq 80– 128 9– 138 11– 141 13– 64 69– 183 0– 44 44– 170 86– 250 125– 218 141– 282 144– 288 134– 246 150– 260 170– 260 190– 260 134– 211 10– 105 104– 280 56– 136 59– 131 129– 222 148– 233 184– 366 liq 17– 75 39– 179 93– 251 137– 177 94– 214

top of rh base of rh

201.8 220.0 195.12 227.60 215.23 96 184.9 137.6 142.7 220.1 202.01 183.7 ⫺75.6 181.9

short standard long

DEAN #37261

LEFT

(McGHP)

5.52

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance 1-Nonene Octadecane 1-Octadecanethiol 1-Octadecanol 1-Octadecene Octane 1-Octanethiol 1-Octanol 2-Octanol 3-Octanol 4-Octanol 1-Octene 5-Oxyhydrindene Pentachloroethane Pentadecane 1-Pentadecene 1,2-Pentadiene 1,3-Pentadiene cis trans 1,4-Pentadiene 2,3-Pentadiene Pentafluorobenzene Pentafluorochloroacetone Pentafluorochlorethane Pentafluorophenol 2,2,3,3,3-Pentafluoropropanol Pentafluorotoluene bis-Pentamethyldisilanoxydisilane bis-Pentamethyldisilanyl ether Pentane Pentanenitrile 1-Pentanethiol Pentanoic acid 1-Pentanol 2-Pentanol 3-Pentanol 2-Pentanone 3-Pentanone 1-Pentene 2-Pentene cis trans 1-Pentyne 2-Pentyne Perdeuterobenzene Perdeuterocyclohexane Perfluorobutane Perfluorobutene

Eq.

Range, ⬚C

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

35– 175 172– 352 liq 120– 218 19– 152 76– 229 0– 80 70– 195 72– 180 76– 176 71– 176 15– 147 120– 251 25– 162 136– 304 ⫺42 to ⫺26 ⫺21 to 67 ⫺43 to ⫺22 ⫺18 to 66 ⫺45 to ⫺20 ⫺18 to 64 ⫺57 to ⫺37 ⫺33 to 47 ⫺39 to ⫺18 ⫺14 to 70 49– 94 ⫺40 to 32 ⫺95 to ⫺39 105– 155 0– 23 39– 138 169– 201 88– 183 ⫺50 to 58 69– 141 19– 153 72– 174 37– 138 25– 120 21– 116 56– 111 56– 111 ⫺55 to 51 ⫺49 to 58 ⫺49 to 58 ⫺44 to 61 ⫺33 to 78 10– 82 10– 80 ⫺39 to ⫺4 ⫺28 to 20

A 6.954 7.002 7.096 6.461 7.060 6.918 6.969 12.070 6.837 6.388 5.221 5.739 6.934 9.213 6.740 7.023 7.022 7.259 6.918 7.193 6.910 7.102 6.913 7.174 6.835 7.202 6.962 7.036 6.848 6.833 7.066 6.308 7.084 8.556 8.161 6.852 7.104 6.933 5.412 7.177 7.275 7.414 7.021 7.025 6.844 6.843 6.899 6.967 7.046 6.892 6.837 7.035 9.222

B 30 2 6 65 68 09 1 90 8 5 6 95 7 59 91 90 20 87 89 12 17 01 43 53 16 65 4 34 0 7 78 64 44 96 9 11 58 75 93 93 29 24 08 83 34 14 35 86 1

1 1 2 1 1 1 1 4 1 1

1 3 1 1 1 1 1 1 1 1 1 1 1 1 1 1

1 1 3 2 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2

436.20 894.3 061 599 997.4 351.99 593.0 506.8 310.62 060.4 560.3 760.5 355.46 665.8 378 789.95 788.58 250.293 104.991 223.602 101.923 185.389 103.840 155.378 017.995 231.768 126.837 254.07 925.3 802.97 379.15 830.56 392.20 051.316 575.250 064.84 519.4 369.479 591 314.56 271.92 354.42 313.85 310.28 044.01 052.44 080.76 092.52 189.87 198.39 190.38 990.27 401.6

C 205.69 143.30 129 90 147.50 209.15 190.61 319.9 136.05 122.5 64.7 89.5 213.05 326.4 197 161.38 163.347 241.96 228.85 240.62 229.37 239.41 231.72 244.30 231.46 237.56 227.84 216.02 225.4 242.27 183.91 153.8 213.67 258.85 273.32 233.01 218.4 211.31 60 168.11 170.37 183.41 215.01 214.19 233.50 228.69 232.57 227.18 229.60 219.43 222.40 240.4 382

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.53

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance Perfluorocyclobutane Perfluorocyclohexane Perfluorocyclopentane Perfluoroheptane Perfluorohexane Perfluoromethylcyclohexane Perfluorooctane Perfluoropentane Perfluoropiperidine Perfluoropropane Perfluoropropene Phenanthrene Phenol ␤-Phenylethyl acetate ␣-Phenylethyl alcohol o-Phenylethylphenol p-Phenylethylphenol Phenylisocyanate 4-Phenylphenol Phosgene Phthalic anhydride ␣-Pinene ␤-Pinene Piperidine Propadiene Propane 1-Propanethiol 2-Propanethiol 1-Propanol 2-Propanol 2-Propen-1-ol Propionic acid Propionic anhydride Propionitrile Propiophenone Propyl acetate 1-Propylamine 2-Propylamine n-Propylbenzene n-Propyl borate n-Propyl caprate n-Propyl caproate n-Propyl caprylate n-Propyl cellosolve n-Propylcyclohexane n-Propylcyclopentane Propylene 1,2-Propylene oxide n-Propyl formate n-Propyl laurate n-Propyl myristate n-Propyl nitrate n-Propyl palmitate

Eq.

Range, ⬚C

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

⫺32 to 0 19– 65 17– 56 ⫺2 to 106 30– 57 33– 111 37– 105 9– 65 29– 81 ⫺79 to ⫺36 ⫺41 to 20 176– 379 107– 182 149– 233 82– 190 169– 250 174– 251 10– 80 177– 308 ⫺68 to 68 160– 285 19– 156 19– 166 42– 144 ⫺99 to ⫺16 ⫺108 to ⫺25 ⫺25 to 91 ⫺37 to 75 2– 120 0– 101 21– 97 56– 139.5 67– 167 ⫺84 to 22 132– 201 39– 101 23– 77 4– 61 43– 188 85– 179 97– 186 43– 120 70– 153 77– 149 40– 186 21– 158 ⫺112 to ⫺32 ⫺35 to 130 26– 82 124– 205 147– 200 0– 70 166– 204

A 6.815 6.04 7.039 6.937 6.875 6.824 5.902 7.017 6.853 6.919 7.355 7.260 7.133 6.834 1.508 4.506 4.304 ⫺0.708 8.657 6.842 8.022 6.852 6.898 6.855 5.713 6.803 6.928 6.877 7.847 8.117 11.187 6.403 5.819 5.278 7.370 7.016 6.926 6.890 6.951 7.399 8.701 8.667 8.516 7.146 6.886 6.903 6.778 7.064 6.848 8.068 9.216 6.954 14.129

top of rh base of rh

29 6 72 2 06 5 9 4 4 82 0 3 0 1 0 5 97 5 4 69 7 38 46 34 67 78 0 5 2 15 51 25 42 8 22 1 7 4 46 92 11 92 9 8 9 2

B

C

862.49 597 1 069.3 1 181.14 1 080.8 1 133.76 1 225.93 1 072.9 1 059.95 825.8 1 012.1 2 379.04 1 516.79 1 555.2 91 516.8 459.3 106.4 3 022.8 941.25 2 868.5 1 446.4 1 511.7 1 238.80 458.06 804.00 1 183.307 1 113.895 1 499.21 1 580.92 4 068.5 950.2 810.3 665.52 1 894 1 282.28 1 044.05 985.69 1 491.297 1 741 2 945.99 2 556.0 2 599.5 1 440.6 1 460.800 1 384.386 770.85 1 113.6 1 127 2 692.4 3 744.68 1 294.4 9 759.2

225.19 136 234.6 208.66 213.4 211.22 198.99 230.0 217.2 241.2 257 203.76 174.95 160.8 ⫺263 ⫺32.1 ⫺52.4 ⫺146.6 216.1 230 208.0 210.2 205.43 196.07 247.04 224.62 226.16 204.64 219.61 392.7 130.3 108.7 159.10 205 208.60 210.84 214.07 207.14 206 253.63 262.9 246.2 187.7 207.94 213.16 245.51 232 203 222.5 272.87 206.7 539.7

short standard long

DEAN #37261

LEFT

(McGHP)

5.54

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance o-(n-Propyl)phenol p-(n-Propyl)phenol n-Propyl phenyl ether Propyne Pseudocumenol Pyrene Pyridine Pyrogallol Pyrrole Quinaldine Quinoline Spiropentane Styrene Terpenyl acetate ␣-Terpineol Terpinolene Tetrabutyl tin 1,1,2,2-Tetrachloro-1,2-difluoroethane 1,1,1,2-Tetrachloroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetrachloromethane Tetradecane 1-Tetradecanethiol 1-Tetradecanol 1-Tetradecene 1,2,3,4-Tetrafluorobenzene 1,2,3,5-Tetrafluorobenzene Tetrafluoroethylene Tetrafluoromethane Tetrahydrofuran Tetraiodothiophene Tetralin 1,2,3,4-Tetramethylbenzene 1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene 2,2,3,3-Tetramethylbutane Tetramethyl lead 2,2,3,3-Tetramethylpentane 2,2,3,4-Tetramethylpentane 2,2,4,4-Tetramethylpentane Tetramethylsilane 2-Thiabutane Thiacyclobutane Thiacyclohexane Thiacyclopentane Thiacyclopropane 3-Thiaheptane 4-Thiaheptane 2-Thiahexane 3-Thiahexane

Eq.

Range, ⬚C

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

104– 222 0– 234 101– 190 ⫺90 to ⫺6 107– 232 200– 395 67– 153 177– 309 66– 166 178– 248 164– 238 3– 71 32– 82 37– 150 84– 217 40– 179 100– 300 10– 91.5

9.215 8.329 7.734 6.784 6.915 5.618 7.041 6.092 7.294 7.179 6.817 6.917 7.140 6.443 8.141 7.169 6.545 10.995

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

59– 130 25– 130 37– 120

6.898 6.631 6.976 6.879 7.013 7.048 6.674 7.030 7.084 6.986 6.896 6.972 6.995 5.585 7.070 7.059 7.077 7.080 6.876 6.937 6.830 6.834 6.796 6.822 6.938 7.016 6.905 6.995 7.037 6.941 6.935 6.945 6.933

122– 286 130– 264 119– 283 6– 50 6– 50 ⫺131 to ⫺65 23– 100 ⫺65 to 24 94– 206 80– 217 75– 228 74– 227 0– 65 0– 60 57– 141 52– 134 43– 123 ⫺64 to 21 ⫺26 to 90 ⫺5 to 120 29– 170 14– 148 ⫺35 to 77 33– 172 32– 170 17– 150 14– 144

A

B

6 3 85 4 15 70 00 59 00 16 46 2

75 7 83 26 00 5 1 65 6 17 59 31 15 44 55 4 9 0 65 7 60 18 20 39 49 67 18 40 25 02 77 83 80

C

3 254 2 661 2 146.2 803.73 1 547 1 122.0 1 373.80 1 031 1 501.56 1 857.84 1 668.73 1 090.08 1 574.51 1 377.27 2 479.4 1 706 1 649 4 437.1

292 254 252.3 229.08 152 15.2 214.98 12 210.42 184.50 186.26 231.10 224.09 143.85 253.7 211 148 455.2

1 1 1 1 1 1 1 1 1 1

209.74 179.9 217.53 226.41 167.72 151.9 54.0 171.52 223.49 218.35 245.93 260.10 226.25 175.59 208.26 199.48 201.14 201.43 226.36 219.1 213.84 214.94 216.02 235.62 224.78 224.51 211.72 219.61 232.42 205.81 205.73 212.07 212.51

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

365.88 228.1 386.92 212.021 740.88 909.2 204.5 754.09 339.23 245.20 683.84 540.50 202.29 871.25 741.30 690.54 675.43 672.43 329.93 335.3 398.67 375.59 324.59 033.72 182.562 321.331 422.47 401.939 194.37 421.32 413.44 363.808 341.57

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.55

PHYSICAL PROPERTIES

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance

Eq.

Range, ⬚C

A

2-Thiapentane 3-Thiapentane 2-Thiapropane Thiazole Thiophene Toluene o-Toluidine m-Toluidine p-Toluidine m-Tolyl pentafluoropropionate p-Tolyl pentafluoropropionate m-Tolyl trifluoroacetate p-Tolyl trifluoroacetate Tribromomethane 1,2,3-Tribromopropane Trichloroacetic acid Trichloroacetonitrile Trichloroacetyl chloride 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane Trichlorosilane bis-Trichlorosilylethane 1,1,1-Trichloro-2,2,2-trifluoroethane 1,1,2-Trichloro-1,2,2-trifluoroethane Tridecane 1-Tridecene Triethanolamine Triethyl aluminum Triethylamine Triethyl borate Triethylsilanol Trifluoroacetic acid Trifluoroacetic anhydride Trifluoroacetonitrile 1,3,5-Trifluorobenzene Trifluorochloroethylene 1,1,1-Trifluoroethane 2,2,2-Trifluoroethanol Trifluoromethane bis-(Trifluoromethyl)-acetoxyphosphine 2,2,2-Trifluoro-1-methylbenzene bis-(Trifluoromethyl)-chlorophosphine Trifluoromethylhypofluorite bis-(Trifluoromethyl)-iodophosphine Triisobutylene

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

⫺4 to 120 ⫺13 to 109 ⫺47 to 58 63– 118 ⫺12 to 108 6– 137 118– 200 122– 203

6.955 6.928 6.948 7.142 6.959 6.954 7.082 7.093 7.260 7.427 8.078 7.681 7.913 6.821 7.037 7.273 7.183 6.990 8.643 6.951 6.518 6.884 6.773 7.835 4.437

1

⫺25 to 83

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

107– 267 105– 264 252– 305 57– 126 50– 95 29– 109 24– 140 12– 72 ⫺2 to 39 ⫺132 to ⫺68 6– 50 ⫺67 to ⫺11 ⫺110 to ⫺48 ⫺0.5 to 25 ⫺128 to ⫺82 0– 40

1 1

55– 139 ⫺80 to 0

1 1 1

98– 174 99– 176 91– 166 92– 169 30– 101 128– 205 112– 198 17– 83 32– 119 ⫺6 to 17 50– 114 18– 86 2– 32 91– 160 14– 36

B 45 36 79 01 26 64 03 67 22 20 6 0 8 8 2 0 5 75 4 85 3 28 9 11 3

6.880 3

1 1 1 1 1 1 1 1 1 1 2 1 2 1 1 1 1 1 2 1 1 1 1 2

284.32 257.833 090.755 425.35 246.02 344.800 627.72 631.43 758.55 707.59 223.8 874.84 055.41 376.7 735.32 594.3 368.3 390.47 136.6 314.41 018.6 043.004 009.0 241.769 204.1

C 219.66 218.66 230.80 216.26 221.35 219.48 187.13 183.91 201.0 201.70 252.1 223.48 238.99 201.0 195.42 165.4 232.5 220.11 302.8 209.20 192.7 236.88 227.2 249.84 83.9

1 099.9

227.5

1 1 4 4

690.67 672.00 542.78 466.59 695.7 641.7 756.1 895 026.1 773.82 197.13 848.33 788.20 978.13 705.33 426.254

174.22 174.95 297.76 322.87 144.8 236.3 202.4 273 202.0 249.9 219.12 293.64 243.23 173.06 249.78 220.37

6.970 45 7.661 06

1 306.35 1 386.652

217.38 267.14

145– 189 0– 47

6.950 6 6.901 39

650.1 1 180.723

⫺18.4 222.95

56– 179

7.002 1

1 613.47

212.5

7.007 6.981 10.067 11.646 5.858 7.511 7.793 8.389 6.135 7.127 6.919 6.896 6.903 6.788 7.088 7.391

top of rh base of rh

56 02 5 1 8 1 7 8 6 8 16 78 2 6 31

1 1 1 1 1

1

short standard long

DEAN #37261

LEFT

(McGHP)

5.56

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.9 Vapor Pressures of Various Organic Compounds (Continued) Substance Trimethyl aluminum Trimethylamine 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene 2,2,3-Trimethylbutane Trimethylchlorosilane 1,1,3-Trimethylcyclohexane 1,1,2-Trimethylcyclopentane 1,1,3-Trimethylcyclopentane 1,2,4-Trimethylcyclopentane cis, cis, trans cis, trans, cis 1,3,5-Trimethyl-2-ethylbenzene 1,4,5-Trimethyl-2-ethylbenzene 2,2,5-Trimethylhexane 2,4,4-Trimethylhexane Trimethylhydrazine O,N,N-Trimethylhydroxylamine 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane 2,3,4-Trimethylpentane 2,4,4-Trimethyl-1-pentene 2,4,4-Trimethyl-2-pentene 2,3,5-Trimethylphenol Trimethylsilanol 2,4,5-Trimethylstyrene 2,4,6-Trimethylstyrene 1,2,4-Trinitrobenzene 1,3,5-Trinitrobenzene 2,4,6-Trinitrobenzene 2,4,6-Trinitrotoluene ␣-Trioxane Trivinylarsine Trivinyl bismuth Trivinylphosphine Trivinylstibine Undecane 1-Undecanethiol 1-Undecene Urethane Vinyl acetate o-Xylene m-Xylene p-Xylene 2,3-Xylenol 2,4-Xylenol 2,5-Xylenol 2,6-Xylenol 3,4-Xylenol 3,5-Xylenol

Eq.

Range, ⬚C

A

1 1 1 1 1 1 1 1 1 1

64– 127 ⫺80 to 3 57– 205 52– 198 49– 193 ⫺19 to 106 2– 55 55– 137 36– 115 29– 106

7.570 6.857 7.040 7.043 7.074 6.792 7.055 6.839 6.822 6.809

1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1

39– 118 33– 110 88– 210 87– 132 46– 125 51– 131 ⫺16 to 14 ⫺79 to 23

6.857 6.851 6.790 3.029 6.837 6.856 7.106 6.765 6.825 6.811 6.843 6.853 6.834 6.859 7.080 8.126 7.331 7.089 3.194 5.534 9.621 7.671 7.818 7.894 7.237 7.928 8.322 6.972 7.012 6.966 7.421 7.210 6.998 7.009 6.990 7.053 7.055 7.051 7.070 7.079 7.130

24– 100 36– 114 ⫺3 to 128 2– 131 186– 247 18– 85 79– 216 90– 208 250– 300 202– 312 249– 342 230– 250 56– 114 22– 66 20– 74 16– 61 20– 70 75– 226 72– 222 22– 72 32– 172 28– 166 27– 166 149– 218 144– 212 144– 212 145– 204 172– 229 155– 223

B

C

29 55 82 83 36 30 8 51 38 31

1 734.72 955.94 1 593.958 1 573.257 1 569.622 1 200.563 1 245.5 1 394.88 1 309.81 1 275.92

242.78 237.52 207.08 208.56 209.58 226.05 240.7 215.73 218.58 219.89

38 3 8 3 75 54 80 8 46 89 53 96 57 22 12 6 5 1

1 335.69 1 307.10 1 505.8 116.4 1 325.54 1 371.81 1 189.88 979.55 1 294.88 1 257.84 1 328.05 1 315.08 1 273.416 1 272.717 1 685.90 1 657.6 1 880.7 1 702.61 87 993.6 4 987.9 2 669.4 1 783.3 2 115.6 1 667.0 2 102.0 2 446.3 1 569.57 1 767.4 1 563.21 1 758.21 1 296.13 1 474.679 1 462.266 1 453.430 1 617.57 1 587.46 1 592.70 1 628.32 1 621.45 1 639.86

219.16 219.92 174.7 ⫺34.6 210.91 214.40 222.06 222.2 218.42 220.74 220.38 217.53 220.62 214.99 166.14 219.2 205.7 195.93 ⫺199 11.2 329.9 205.6 247.1 293.9 215.1 301.3 303.8 187.70 170.4 189.87 205.0 226.66 213.69 215.11 215.31 170.74 169.34 170.74 187.60 159.26 164.16

5 1 52 6 1 2 4 1 20 2 77 64 1 91 08 52 97 39 56 70 19 76

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DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.57

PHYSICAL PROPERTIES

5.3

top of rh base of rh cap height base of text

BOILING POINTS

TABLE 5.10 Boiling Points of Water A. Barometric Pressures at Various Temperatures Temp. ⬚C.

0.0⬚

0.2⬚

0.4⬚

0.6⬚

0.8⬚

80 81 82 83 84

mm of Hg 355.40 370.03 385.16 400.81 416.99

mm of Hg 358.28 373.01 388.25 404.00 420.29

mm of Hg 361.19 376.02 391.36 407.22 423.61

mm of Hg 364.11 379.05 394.49 410.45 426.95

mm of Hg 367.06 382.09 397.64 413.71 430.32

85 86 87 88 89

433.71 450.99 468.84 487.28 506.32

437.12 454.51 472.48 491.04 510.20

440.55 458.06 476.14 494.82 514.11

444.01 461.63 479.83 498.63 518.04

447.49 465.22 483.54 502.46 521.99

90 91 92 93 94

525.97 546.26 567.20 588.80 611.08

529.98 550.40 571.47 593.20 615.62

534.01 554.56 575.76 597.63 620.19

538.07 558.75 580.08 602.09 624.79

542.15 562.96 584.43 606.57 629.41

95 96 97 98 99 100

634.06 657.75 682.18 707.35 733.28 760.00

638.74 662.58 687.15 712.47 738.56 765.44

643.45 667.43 692.15 717.63 743.87 770.91

648.19 672.32 697.19 722.81 749.22 776.42

652.96 677.23 702.25 728.03 754.59 781.95

B. Boiling Points of Water at Various Pressures Pressure, atm.

Boiling Point, ⬚C.

Pressure, atm.

Boiling Point, ⬚C.

Pressure, atm.

Boiling Point, ⬚C.

Pressure, atm.

Boiling Point, ⬚C.

0.5 1 2 3 4

80.9 100.0 119.6 132.9 142.9

7 8 9 10 11

164.2 169.6 174.5 179.0 183.2

14 15 16 17 18

194.1 197.4 200.4 203.4 206.1

21 22 23 24 25

213.9 216.2 218.5 220.8 222.9

5 6

151.1 158.1

12 13

187.1 190.7

19 20

208.8 211.4

26 27

225.0 227.0

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DEAN #37261

LEFT

(McGHP)

5.58

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SECTION 5

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TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures An azeotrope is a mixture that cannot be separated by distillation. A. Binary azeotropes containing water Composition, wt %

System

BP of azeotrope, ⬚C

Water

Other component

52.5 79.78 64.4 43

47.5 20.22 35.6 57

32.6 28.4

67.4 71.6

22.6

77.4

82.3 79 81.6 89 81.6 71 97.8

17.7 21 18.4 11 18.4 29 2.2

4 27.7 71.7 12.6 42.5 26.8 11.7 54.4 36.5 36.0 27.5 67.2 90 58 83 90.8 87.5 98.75 91

96 72.3 28.3 87.4 57.5 73.2 88.3 45.6 63.5 64.0 72.5 32.8 10 42 17 9.2 12.5 1.25 9

80

20

Inorganic acids Hydrogen bromide Hydrogen chloride Hydrogen fluoride Hydrogen iodide Hydrogen peroxide Nitric acid Perchloric acid

126 108.58 111.35 127 zeotrope 120.7 203 Organic acids

Formic acid Acetic acid Propionic acid Isobutyric acid Butyric acid Pentanoic acid Isopentanoic acid Perfluorobutyric acid Crotonic acid

107.2 zeotrope 99.9 99.3 99.4 99.8 99.5 97 99.9 Alcohols

Ethanol Allyl alcohol 1-Propanol 2-Propanol 1-Butanol 2-Butanol 2-Methyl-2-propanol 1-Pentanol 2-Pentanol 3-Pentanol 2,2-Dimethyl-2-propanol 1-Hexanol 1-Octanol Cyclopentanol 1-Heptanol Phenol 2-Methoxyphenol 1-Phenylphenol Benzyl alcohol 2,3-Dimethyl-2,3-butanediol Furfuryl alcohol

78.17 88.9 71.7 80.3 92.7 87.0 79.9 95.8 91.7 91.7 87.35 97.8 99.4 96.25 98.7 99.52 99.5 99.95 99.9 zeotrope 98.5

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.59

PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Water

Other component

2 6 19 28.5 65

98 94 81 71.5 35

15 74 35 41.3 48 60 62.8 51.8 50.5 92.8 38 79.7 80.8 83.9 97.5

85 26 65 58.7 52 40 37.2 48.2 49.5 7.2 62 20.3 19.2 16.1 2.5

2.8 2.8 17 17.2 8.3 2.2 12 28.4

97.2 97.2 83 82.8 91.7 97.8 88 71.6

5 3 2.3 7.8 14.5 21 28.4 80 8.47 14.7

95 97 97.7 92.2 85.5 79 71.6 20 91.53 85.3

Aldehydes Propionaldehyde Butyraldehyde Pentanal Paraldehyde Furaldehyde

47.5 68 83 90 97.5 Amines

N-Methylbutylamine Furfurylamine Piperidine Pyridine 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 2,6-Dimethylpyridine Dibutylamine Dihexylamine Triallylamine Tributylamine Aniline N-Ethylaniline 1-Methyl-2-(2-pyridyl)pyrrolidine

82.7 99 92.8 93.6 93.5 97 97.35 96.02 97 99.8 95 99.65 98.6 99.2 99.85 Halogenated hydrocarbons

Chloroform Carbon tetrachloride Trichloroethylene Tetrachloroethylene 1,2-Dichloroethane 1-Chloropropane 1,2-Dichloropropane Chlorobenzene

56.1 42.6 73.4 88.5 72 44 78 90.2 Esters

Ethyl formate Isopropyl formate Propyl formate Isobutyl formate Butyl formate Isopentyl formate Pentyl formate Benzyl formate Ethyl acetate Allyl acetate

52.6 65.0 71.6 80.4 83.8 90.2 91.6 99.2 70.38 83

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DEAN #37261

LEFT

(McGHP)

5.60

INTERACTIVE

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TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Water

Other component

10.6 14 16.5 28.7 36.3 41 61 75.1 87.5 3.9 10 19.9 23 52.2 48.5 11.5 21.5 36.4 46 53 63.5 6.8 15.2 30.8 39.4 56.0 19.2 30.2 45.2 55.8 74.1 40 54 79.2 84.0 90.9 94 95.6 91.3 95.5 97.5 98.0 45.1 75.5 7.2 74 38 80

89.4 86 83.5 71.3 63.7 59 39 24.9 12.5 96.1 90 80.1 77 47.8 51.5 88.5 78.5 63.6 54 47 36.5 93.2 84.8 69.2 60.6 44.0 80.8 69.8 54.8 44.2 25.9 60 46 20.8 16.0 9.1 6 4.4 8.7 4.5 2.5 2.0 54.9 24.5 92.8 26 62 20

Esters (continued) Isopropyl acetate Propyl acetate Isobutyl acetate Butyl acetate Isopentyl acetate Pentyl acetate Hexyl acetate Phenyl acetate Benzyl acetate Methyl propionate Ethyl propionate Isopropyl propionate Propyl propionate Isobutyl propionate Isopentyl propionate Methyl butyrate Ethyl butyrate Propyl butyrate Isobutyl butyrate Butyl butyrate Isopentyl butyrate Methyl isobutyrate Ethyl isobutyrate Propyl isobutyrate Isobutyl isobutyrate Isopentyl isobutyrate Methyl isopentanoate Ethyl isopentanoate Propyl isopentanoate Isobutyl isopentanoate Isopentyl isopentanoate Ethyl pentanoate Ethyl hexanoate Methyl benzoate Ethyl benzoate Propyl benzoate Butyl benzoate Isopentyl benzoate Ethyl phenylacetate Methyl cinnamate Methyl phthalate Diethyl o-phthalate Ethyl chloroacetate Butyl chloroacetate Methyl acrylate Isobutyl carbonate Ethyl crotonate Methyl lactate

76.6 82.4 87.4 90.2 93.8 95.2 97.4 98.9 99.6 71.4 81.2 85.2 88.9 92.75 96.55 82.7 87.9 94.1 96.3 97.2 98.05 77.7 85.2 92.2 95.5 97.4 87.2 92.2 96.2 97.4 98.8 94.5 97.2 99.08 99.4 99.7 99.9 99.9 99.7 99.9 99.95 99.98 95.2 98.12 71 98.6 93.5 99

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.61

PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Water

Other component

84.6 22 20 25 73

15.4 78 80 75 27

1.5 1.3 4 4.5 11.9 23 33 54 14.5 96.75 40.5

98.5 98.7 96 95.5 88.1 77 67 46 85.5 3.25 59.5

1.4 5.6 12.9 11.1 82 96.0 98 2.6 8.93 8.4 28.7 8.83 13.5 33.0 35.8 43.8 84

98.6 94.4 87.1 88.9 18 4.0 2 97.4 91.07 91.6 71.3 91.17 86.5 67.0 64.2 56.2 16

11 19.5 42.4 24.3

89 80.5 57.6 75.7

Esters (continued) 1,2-Ethanediol diacetate Ethyl nitrate Propyl nitrate Isobutyl nitrate Methyl sulfate

99.7 74.35 84.8 89.0 98.6 Ethers

Ethyl vinyl ether Diethyl ether Ethyl propyl ether Diisopropyl ether Butyl ethyl ether Diisobutyl ether Dibutyl ether Diisopentyl ether 1,1-Diethoxyethane Diphenyl ether Methoxybenzene

34.6 34.2 59.5 62.2 76.6 88.6 92.9 97.4 82.6 99.33 95.5 Hydrocarbons

Pentane Hexane Heptane 2,2,4-Trimethylpentane Nonane Undecane Dodecane Acrolein Cyclohexene Cyclohexane 1-Octene Benzene Toluene Ethylbenzene m-Xylene Isopropylbenzene Naphthalene

34.6 61.6 79.2 78.8 94.8 98.85 99.45 52.4 70.8 69.5 88.0 69.25 84.1 92.0 92 95 98.8 Ketones

Acetone 2-Butanone 2-Pentanone Cyclopentanone 4-Methyl-2-pentanone

zeotrope 73.5 83.3 94.6 87.9

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DEAN #37261

LEFT

(McGHP)

5.62

INTERACTIVE

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SECTION 5

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TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt % BP of azeotrope, ⬚C

System

Water

Other component

48 42.2 40.5 87.3 34.8

52 57.8 59.5 12.7 65.2

16.3 23 32.5 14.3

83.7 l77 67.5 85.7

32.3

67.7

23.6 28.5 11.7 30 2.8

76.4 71.5 88.3 70 97.2

Ketones (continued) 2-Heptanone 3-Heptanone 4-Heptanone 4-Hydroxy-4-methyl-2-pentanone 4-Methyl-3-penten-2-one

95 94.6 94.3 98.8 91.8 Nitriles

Acetonitrile Isobutyronitrile Butyronitrile Acrylonitrile

76.5 82.5 88.7 70.6 Miscellaneous

Hydrazine Acetamide Nitromethane Nitroethane 2,5-Dimethylfuran Trioxane Carbon disulfide

120 zeotrope 83.59 87.22 77.0 91.4 42.6 B. Binary azeotropes containing organic acids

Composition, wt %

System

BP of azeotrope, ⬚C

Acid

Other component

4 20 28 29 70 46.5 56.5 63 31 50 74 71.8 73

96 80 72 71 30 53.5 43.5 37 69 50 26 28.2 27

Formic acid 2-Methylbutane Pentane Hexane Methylcyclopentane Cyclohexane Methylcyclohexane Heptane Octane Benzene Toluene o-Xylene m-Xylene Styrene

27.2 34.2 60.6 63.3 70.7 80.2 78.2 90.5 71.05 85.8 95.5 92.8 97.8

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.63

PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Acid

Other component

6 15 18.5 25 50 3 51.5 14 27 14 8 1.5 19 68 59 27 83 61.4 25 32 33 45.5 35 62 83 17

94 85 81.5 75 50 97 48.5 86 73 86 92 98.5 81 32 41 73 17 38.6 75 68 67 54.5 65 38 17 83

6.0 23 53.7 69 79.5 95 9.6 31 2.0 28.1 78 72.5 72 66 85.7 84 67 96

94.0 67 46.3 31 20.5 5 90.4 69 98.0 71.9 22 27.5 28 34 14.3 16 33 4

Formic acid (continued) Iodomethane Chloroform Carbon tetrachloride Trichloroethylene Tetrachloroethylene Bromoethane 1,2-Dibromoethane 1,2-Dichloroethane 1-Bromopropane 2-Bromopropane 1-Chloropropane 2-Chloropropane 1-Chloro-2-methylpropane Bromobenzene Chlorobenzene Fluorobenzene o-Chlorotoluene Pyridine 2-Methylpyridine 2-Pentanone 3-Pentanone Nitromethane Diethyl sulfide Diisopropyl sulfide Dipropyl sulfide Carbon disulfide

42.1 59.15 66.65 74.1 88.2 38.2 94.7 77.4 64.7 56.0 45.6 34.7 63.0 98.1 93.7 73.0 100.2 127.43 158.0 105.3 105.4 97.07 82.2 93.5 98.0 42.55 Acetic acid

Hexane Heptane Octane Nonane Decane Undecane Cyclohexane Methylcyclohexane Benzene Toluene o-Xylene m-Xylene p-Xylene Ethylbenzene Styrene Isopropylbenzene Triethylamine Nitromethane

68.3 91.7 105.7 112.9 116.75 117.9 78.8 96.3 80.05 100.6 116.6 115.35 115.25 114.65 116.8 116.0 163 101.2

short standard long

DEAN #37261

LEFT

(McGHP)

5.64

INTERACTIVE

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SECTION 5

cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Acid

Other component

30 51.1 40.4 30.4 30.3 22.9 98.46 96.2 61.5 55 9 18 12 58.5 80.5 77 48

70 48.9 59.6 69.6 69.7 77.1 1.54 3.8 38.5 45 91 82 88 41.5 19.5 23 52

2 21.5 54.0 80.5 43 34 77 65 75 65 58.5 96 67.2 55.0 17.5 9 18 45

98 78.5 46.0 19.5 57 66 23 35 25 35 41.5 4 32.8 45.0 82.5 91 82 55

84.4 10 6 5.5 4

15.5 90 94 94.5 96

Acetic acid (continued) Nitroethane Pyridine 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 2,6-Dimethylpyridine Carbon tetrachloride Trichloroethylene Tetrachloroethylene 1,2-Dibromoethane 2-Iodopropane 1-Bromobutane 1-Bromo-2-methylpropane Chlorobenzene Trichloronitromethane 1,4-Dioxane Diisopropyl sulfide

112.4 138.1 144.1 152.5 154.3 148.1 76 86.5 107.4 114.4 88.3 97.6 90.2 114.7 107.65 119.5 111.5 Propionic acid

Heptane Octane Nonane Decane o-Xylene p-Xylene 1,3,5-Trimethylbenzene Isopropylbenzene Propylbenzene Camphene ␣-Pinene Methoxybenzene Pyridine 2-Methylpyridine 1,2-Dibromoethane 1-Iodo-2-methylpropane Chlorobenzene Dipropyl sulfide

97.8 120.9 134.3 139.8 135.4 132.5 139.3 139.0 139.5 138.0 136.4 140.8 148.6 154.5 127.8 119.5 128.9 136.5 Butyric acid

Undecane o-Xylene m-Xylene p-Xylene Ethylbenzene

162.4 143.0 138.5 137.8 135.8

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

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PHYSICAL PROPERTIES

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TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Acid

Other component

Butyric acid (continued) Styrene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Isopropylbenzene Propylbenzene Butylbenzene Naphthalene Indene Camphene Methoxybenzene Pyridine 2-Furaldehyde 1,2-Dibromoethane 1-Iodobutane Chlorobenzene 1,4-Dichlorobenzene o-Bromotoluene m-Bromotoluene p-Bromotoluene ␣-Chlorotoluene Ethyl bromoacetate Propyl chloroacetate

143.5 159.5 158.0 149.5 154.5 162.5 zeotrope 163.7 152.3 152.9 163.2 159.4 131.1 129.8 131.75 162.0 163.0 163.6 161.5 160.8 157.4 160.5

15 45 38 20 28 75

85 55 62 80 72 25

84 2.8 12 92.0 42.5 3.5 2.5 2.8 57 72 79.5 75 65 84 40

16 97.2 88 8.0 57.5 96.5 97.5 97.2 43 28 20.5 25 35 16 60

48 22 15 13 27 63 35 49 45 78 42 40 60 6.5 7 35 35 8 85 80 93 40

52 78 85 87 73 37 65 51 55 22 58 60 40 93.5 93 65 65 92 15 20 7 60

Isobutyric acid 2,7-Dimethyloctane o-Xylene m-Xylene p-Xylene Styrene 1,2,4-Trimethylbenzene Isopropylbenzene Propylbenzene Camphene D-Limonene Methoxybenzene Ethyl bromoacetate Ethyl 2-oxopropionate 1,2-Dibromoethane 1-Iodobutane 1-Bromohexane Bromobenzene Chlorobenzene o-Bromotoluene ␣-Chlorotoluene Diisopentyl ether Ethyl bromoacetate

148.6 141.0 139.9 136.4 142.0 152.3 146.8 149.3 148.1 152.5 149.0 153.0 153.0 130.5 128.8 148.0 148.6 131.5 153.9 153.5 154.2 153.0

short standard long

DEAN #37261

LEFT

(McGHP)

5.66

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) C. Binary azeotropes containing alcohol Composition, wt %

System

BP of azeotrope, ⬚C

Alcohol

Other component

7 14 36.4 54 51.5 67.5 83.4 39.1 32 72.5 99.55 95.5 60 87.4 79.44 5.3 32 38 21 15.0 9.5 6 38 27 95 19 54 73 12.1

93 86 63.6 46 48.5 32.5 16.6 60.9 68 27.5 0.45 4.5 40 12.6 20.56 94.7 68 62 79 85.0 90.5 94 62 73 5 81 46 27 87.9

72 14.3 62 71 16.4 9.1

28 85.7 38 29 83.6 90.9

5 7.5 21 29.2 49

95 92.5 79 70.8 51

Methanol Pentane Cyclopentane Cyclohexane Methylcyclohexane Heptane Octane Nonane Benzene Fluorobenzene Toluene Bromomethane Iodomethane Bromodichloromethane Chloroform Carbon tetrachloride Bromoethane 1,2-Dichloroethane Trichloroethylene 1-Bromopropane 2-Bromopropane 1-Chloropropane 2-Chloropropane 2-Iodopropane 1-Chlorobutane Isobutyl formate Methyl acetate Methyl acrylate Methyl nitrate Acetone 1,4-Dioxane Dipropyl ether Methyl tert-butyl ether Diethyl sulfide Carbon disulfide Thiophene Nitromethane

30.9 38.8 53.9 59.2 59.1 62.8 64.1 57.5 59.7 63.5 3.55 37.8 63.8 53.4 55.7 34.9 61.0 59.3 54.5 48.6 40.5 33.4 61.0 57.0 64.6 53.5 62.5 52.5 55.5 zeotrope 63.8 51.3 61.2 39.8 59.7 64.4 Ethanol

Pentane Cyclopentane Hexane Cyclohexane Heptane

34.3 44.7 58.7 64.8 70.9

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.67

PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Alcohol

Other component

78 31.7 75 68 72 96.8 93 34 84.2 37 5 20.5 10.5 6 2.8 44 27 43 20.3 40 76 44 44 41 29 91 56

22 68.3 25 32 28 3.2 7 66 15.8 63 95 79.5 89.5 94 97.2 56 73 57 79.7 60 24 56 56 59 71 9 44

4 18.5 34.7 34.7 70 16.9 51.2

96 81.5 65.3 65.3 30 83.1 48.8

94 92.2 8 3 64 51 48 49 30

6 7.8 92 97 36 49 52 51 70

Ethanol (continued) Octane Benzene Fluorobenzene Toluene Bromodichloromethane Iodomethane Chloroform Trichloronitromethane Carbon tetrachloride 1,2-Dichloroethane 3-Chloro-1-propene 1-Bromopropane 2-Bromopropane 1-Chloropropane 2-Chloropropane 1-Iodopropane 2-Iodopropane 1-Bromobutane 1-Chlorobutane 2-Butanone 1,1-Diethoxyethane Dipropyl ether Acetronitrile Acrylonitrile Nitromethane Carbon disulfide Diethyl sulfide

77.0 67.9 70.0 76.7 75.5 41.2 59.3 77.5 65.0 70.5 44 62.8 55.6 45.0 35.6 75.4 71.5 75.0 65.7 74.8 78.0 74.5 72.5 70.8 76.1 42.6 72.6 1-Propanol

Hexane Cyclohexane Methylcyclohexane Heptane Octane Benzene Toluene o-Xylene m-Xylene p-Xylene Styrene Propyl formate Butyl formate Propyl acetate Ethyl propionate Methyl butyrate Dipropyl ether

65.7 74.7 87.0 84.6 93.9 77.1 92.5 zeotrope 97.1 96.9 97.0 80.7 95.5 94.7 93.4 94.4 85.7

short standard long

DEAN #37261

LEFT

(McGHP)

5.68

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Alcohol

Other component

1-Propanol (continued) 1,1-Diethoxyethane 1,4-Dioxane Chloroform Carbon tetrachloride Trichloronitromethane Iodethane 1,2-Dichloroethane Tetrachloroethylene 1-Bromopropane 1-Chlorobutane Chlorobenzene Fluorobenzene Nitromethane 1-Nitropropane Carbon disulfide

92.4 95.3 zeotrope 73.4 94.1 70 80.7 94.0 69.7 74.8 96.5 80.2 89.1 97.0 45.7

37 55

63 45

92.1 58.5 93 19 52 9 18 80 18 48.4 8.8 94.5

7.9 41.5 7 81 48 91 82 20 82 51.6 91.2 5.5

6 23 32 50.5 84 33.7 30 69 4.2 35 18 43.5 15 20 2.8 20.5 12 42 32 23 25 60 37 56 60 32 63 10 14.1

94 77 68 49.5 16 66.3 70 31 95.8 65 82 56.5 85 80 97.2 79.5 88 58 68 77 75 40 63 44 40 68 37 90 85.9

2-Propanol Pentane Hexane Cyclohexane Heptane Octane Benzene Fluorobenzene Toluene Chloroform Trichloronitromethane Carbon tetrachloride 1,2-Dichloroethane Iodoethane 3-Bromo-1-propene 1-Chloropropane 1-Bromopropane 2-Bromopropane 1-Iodopropane 2-Iodopropane 1-Chlorobutane Ethyl acetate Isopropyl acetate Methyl propionate Acrylonitrile Butylamine 2-Butanone 1,1-Diethoxyethane Ethyl propyl ether Diisopropyl ether

35.5 62.7 69.4 76.4 81.6 71.7 74.5 80.6 60.8 81.9 69.0 74.7 67.1 66.5 46.4 66.8 57.8 79.8 76.0 70.8 75.3 81.3 76.4 71.7 74.7 77.5 81.3 62.0 66.2

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.69

PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Alcohol

Other component

9.5 5 3.2 20 18 45.2 71.5 27.8 75 71.5 68 65.1 23.6 69 47 50 64 17 40 52 63 45 82.5 48 13 97.6 68 7 30 56 52 77.1 35.7 69 32.2 50 45

90.5 95 96.8 80 82 54.8 28.5 72.2 25 28.5 32 34.9 76.4 31 53 50 36 83 60 48 37 55 17.5 52 87 2.4 32 93 70 44 48 22.9 64.3 31 67.8 50 55

14.2 14 5 2.5 32 27 42 56 27 7.4 63 9

85.8 86 95 97.5 68 73 58 44 73 92.6 37 91

1-Butanol Cyclohexane Cyclohexene Hexane Methylcyclohexane Heptane Octane Nonane Toluene o-Xylene m-Xylene p-Xylene Ethylbenzene Butyl formate Isopentyl formate Butyl acetate Isobutyl acetate Ethyl butyrate Ethyl isobutyrate Methyl isopentanoate Ethyl borate Ethyl carbonate Isobutyl nitrate Dibutyl ether Diisobutyl ether 1,1-Diethoxyethane Carbon tetrachloride Tetrachloroethylene 2-Bromo-2-methylpropane 2-Iodo-2-methylpropane Chlorobenzene Paraldehyde Hexaldehyde Ethylenediamine Pyridine 1-Nitropropane Butyronitrile Diisopropyl sulfide

79.8 82.0 68.2 95.3 93.9 108.5 115.9 105.5 116.8 116.5 115.7 115.9 105.8 115.9 117.2 114.5 115.7 109.2 113.5 113.0 116.5 112.8 117.8 113.5 101.0 76.6 110.0 90.2 110.5 115.3 115.8 116.8 124.7 118.6 115.3 113.0 112.0 2-Methyl-2-propanol

Cyclohexene Cyclohexane Methylcyclopentane Hexane Methylcyclohexane Heptane 2,5-Dimethylhexane 1,3-Dimethylcyclohexane 2,2,4-Trimethylpentane Benzene Chlorobenzene Fluorobenzene

80.5 78.3 71.0 68.3 92.6 90.8 98.7 102.2 92.0 79.3 107.1 84.0

short standard long

DEAN #37261

LEFT

(McGHP)

5.70

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Alcohol

Other component

45 80 88.6 40 12 17 92 25 52 12 10 6.2 20 19 20 6.5 21 4 12 36 15.2 36 73

55 20 11.4 60 88 83 8 75 48 88 90 93.8 80 81 80 93.5 79 96 88 64 84.8 64 27

7 30 10 49 94 24 85 14.0 16.5 22.0 65

93 70 90 51 6 76 15 86.0 83.5 78.0 35

14 5 40 75 41 92

86 95 60 25 59 8

2-Methyl-2-propanol (continued) Toluene Ethylbenzene p-Xylene Butyl formate Isobutyl formate Propyl acetate Isobutyl acetate Methyl butyrate Ethyl isobutyrate Methyl chloroacetate Dipropyl ether Isobutyl vinyl ether 1,1-Diethoxyethane 2-Pentanone 3-Pentanone 1,2-Dichloroethane 1-Bromobutane 1-Chlorobutane 2-Bromo-2-methylpropane 2-Iodo-2-methylpropane 1-Nitropropane Isobutyl nitrate Diisopropyl sulfide

101.2 107.2 107.1 103.0 97.4 101.0 107.6 101.3 105.5 107.6 89.5 82.7 98.2 101.8 101.7 83.5 95.0 77.7 88.8 104.0 105.3 105.6 105.8 3-Methyl-1-butanol

Heptane Octane Toluene Ethylbenzene Isopropylbenzene Camphene Bromobenzene o-Fluorotoluene Butyl acetate Paraldehyde Dibutyl ether

97.7 117.0 109.7 125.7 131.6 130.9 131.7 112.1 125.9 123.5 129.8 Cyclohexanol

o-Xylene m-Xylene Propylbenzene Indene Camphene Cineole

143.0 138.9 153.8 160.0 151.9 160.6

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.71

PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Alcohol

Other component

42 4.5 58 50 68 17.36 50 53 55 18 28 85 45

58 95.5 42 50 32 82.64 50 47 45 82 72 15 55

6 35 83.1 46 25 21 47 22 51.0 13 50 78 15 75.4 71.2 67.5 57.0 72.5 52.3 41.9 39.2 53

94 65 16.9 54 75 79 53 78 49.0 87 50 22 85 24.6 29.8 32.5 43.0 27.5 47.7 58.1 60.8 47

60 11 57

40 89 43

61

39

Allyl alcohol Methylcyclohexane Hexane Cyclohexane 2,5-Dimethylhexane Octane Benzene Toluene Propyl acetate Methyl butyrate 1,2-Dichloroethane 3-Iodo-1-propene Chlorobenzene Diethyl sulfide

85.0 65.5 74.0 89.3 93.4 76.75 92.4 94.2 93.8 79.9 89.4 96.2 85.1 Phenol

2,7-Dimethyloctane Decane Tridecane Butylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Indene Camphene Benzaldehyde 1-Octanol 2-Octanol Dipentyl ether Diisopentyl ether 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 2,4-Dimethylpyridine 2,6-Dimethylpyridine 2,4,6-Trimethylpyridine Aniline Ethylene diacetate Iodobenzene

159.5 168.0 180.6 175.0 166.0 163.5 177.8 156.1 175.6 195.4 184.5 180.2 172.2 185.5 188.9 190.0 193.4 185.5 195.2 185.8 195.5 177.7 Benzyl alcohol

Naphthalene D-Limonene 1,3,5-Triethylbenzene o-Cresol m-Cresol

204.1 176.4 203.2 zeotrope 207.1

short standard long

DEAN #37261

LEFT

(McGHP)

5.72

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Alcohol

Other component

62 30 6.5 50 72 12 58 7 85.8

38 70 93.5 50 28 88 42 93 14.2

15 14 38 10.8 48 50 55 80 67 65 72

85 86 62 89.2 52 50 45 20 33 35 28

53 32 73.4 30 15 52 58.5 91 42

47 68 26.6 70 85 48 41.5 9 58

3 23 55 2.3 16.5 87 6.55 6.4 13 19

97 77 45 97.7 83.5 13 93.45 93.6 87 81

Benzyl alcohol (continued) p-Cresol N-Methylaniline N,N-Dimethylaniline N-Ethylaniline N,N-Diethylaniline Iodobenzene Nitrobenzene o-Bromotoluene Borneol

206.8 195.8 193.9 202.8 204.2 187.8 204.0 181.3 205.1 2-Ethoxyethanol

Methylcyclohexane Heptane Octane Toluene Ethylbenzene p-Xylene Styrene Propylbenzene Isopropylbenzene Camphene Propyl butyrate

98.6 96.5 116.0 110.2 127.8 128.6 130.0 134.6 133.2 131.0 133.5 2-Butoxyethanol

Dipentene 1,3,5-Trimethylbenzene Butylbenzene Camphene o-Cresol Phenetole Cineole Benzaldehyde Diisobutyl sulfide

164.0 162.0 169.6 154.5 191.6 167.1 168.9 171.0 163.8 1,2-Ethanediol

Heptane Decane Tridecane Toluene Styrene Stilbene m-Xylene p-Xylene 1,3,5-Trimethylbenzene Propylbenzene

97.9 161.0 188.0 110.1 139.5 196.8 135.1 134.5 156 152

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.73

PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Alcohol

Other component

18 51 60.0 57.2 98.3 26 74.2 82 20 40 66.5 68.5 56 69 27 60 89 51.5 46.5 25 6.4 10.5 60 87 52 47 33.5 42 9.7 79.5 94 4 94.4 30 59 48.5

82 49 40.0 42.8 1.7 74 25.8 18 80 60 33.5 31.5 44 31 73 40 11 48.5 53.5 75 93.6 89.5 40 13 48 53 66.5 58 90.3 20.5 6 96 5.6 70 41 51.5

20 71 65 51 31 33 42 28 32

80 29 35 49 69 67 58 72 68

1,2-Ethanediol (continued) Isopropylbenzene Naphthalene 1-Methylnaphthalene 2-Methylnaphthalene Anthracene Indene Acenaphthene Fluorene Camphene Camphor Biphenyl Diphenylmethane Benzyl alcohol 2-Phenylethanol o-Cresol m-Cresol 3,4-Dimethylphenol Menthol Ethyl benzoate o-Bromotoluene Dibutyl ether Methoxybenzene Diphenyl ether Benzyl phenyl ether Acetophenone 2,4-Dimethylaniline N,N-Dimethylaniline m-Toluidine 2,4,6-Trimethylpyridine Quinoline Tetrachloroethylene 1,2-Dibromoethane Chlorobenzene ␣-Chlorotoluene Nitrobenzene o-Nitrotoluene

147.0 183.9 190.3 189.1 197 168.4 194.65 196.0 152.5 186.2 192.3 193.3 193.1 194.4 189.6 195.2 197.2 188.6 186.1 166.8 139.5 150.5 193.1 195.5 185.7 188.6 175.9 188.6 170.5 196.4 119.1 129.8 130.1 167.0 185.9 188.5 1,2-Ethanediol monoacetate

Indene 1-Octanol Phenol o-Cresol m-Cresol p-Cresol Dipentyl ether Diisopentyl ether m-Bromotoluene

180.0 189.5 197.5 199.5 206.5 206.0 180.8 170.2 182.0

short standard long

DEAN #37261

LEFT

(McGHP)

5.74

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) D. Binary azeotropes containing ketones Composition, wt %

System

BP of azeotrope, ⬚C

Ketone

Other component

36 20 67.5 59 89.5 38.2 48.3 61 78.1 11.5 67 57

64 80 32.5 41 10.5 61.8 51.7 39 21.9 88.5 33 43

40 28.6 70 95 44 69 35 11.8 60 30 38 75

60 71.4 30 5 56 31 65 88.2 40 70 62 25

Acetone Cyclopentane Pentane Cyclohexane Hexane Heptane Diethylamine Methyl acetate Diisopropyl ether Chloroform Carbon tetrachloride Carbon disulfide Ethylene sulfide

41.0 32.5 53.0 49.8 55.9 51.4 55.8 54.2 64.4 56.1 39.3 51.5 2-Butanone

Cyclohexane Hexane Heptane 2,5-Dimethylhexane Benzene 2-Methyl-2-propanol Butylamine Ethyl acetate Methyl propionate Butyl nitrite 1-Chlorobutane Fluorobenzene

71.8 64.2 77.0 79.0 78.33 78.7 74.0 77.1 79.0 76.7 77.0 79.3 E. Miscellaneous binary azeotropes

Composition, wt %

System

BP of azeotrope, ⬚C

Solvent

Other component

18 50.5 56.5 68 11

82 49.5 43.5 32 89

Solvent: acetamide Dipentene Biphenyl Diphenylmethane 1,2-Diphenylethane o-Xylene

169.2 213.0 215.2 218.2 142.6

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.75

PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Solvent

Other component

10 8 12 19 27 43.8 40 17.5 64.2 12 23 6.5 96 88 14 18 24 52 32 97.4

90 92 88 81 73 56.2 60 82.5 35.8 88 77 93.5 4 12 86 82 76 48 68 2.6

13.5 36 57.5 71.5 86.2 95.2 46 13.5 12.0 41.5 83 8 55 28 66

86.5 64 42.5 28.5 13.8 4.8 54 86.5 88.0 58.5 17 92 45 72 34

25.3 56.1 89.9 22.2 13.1 8

74.7 43.9 10.1 77.8 86.9 92

Solvent: acetamide (continued) m-Xylene p-Xylene Styrene 4-Isopropyl-1-methylbenzene Naphthalene 1-Methylnaphthalene 2-Methylnaphthalene Indene Acenaphthene Camphene Camphor Benzaldehyde 3,4-Dimethylphenol 2-Methoxy-4-(2-propenyl)phenol N-Methylaniline N-Ethylaniline N,N-Diethylaniline Diphenyl ether Safrole Tetrachloroethylene

138.4 137.8 144 170.5 199.6 209.8 208.3 177.2 217.1 155.5 199.8 178.6 221.1 220.8 193.8 199.0 198.1 214.6 208.8 120.5 Solvent: aniline

Nonane Decane Undecane Dodecane Tridecane Tetradecane Butylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Indene 1-Octanol o-Cresol Dipentyl ether Diisopentyl ether Hexachloroethane

149.2 167.3 175.3 180.4 182.9 183.9 177.8 168.6 164.3 179.8 183.9 191.3 177.5 169.3 176.8 Solvent: pyridine

Heptane Octane Nonane Toluene Phenol Piperidine

95.6 109.5 115.1 110.1 183.1 106.1

short standard long

DEAN #37261

LEFT

(McGHP)

5.76

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.11 Binary Azeotropic (Constant-Boiling) Mixtures (Continued) Composition, wt % BP of azeotrope, ⬚C

System

Solvent

Other component

14 41.2 11.2 83.2 64 42.7

86 58.8 88.8 16.8 36 57.3

16 64.7 51.9 4.7 99.3 46.3 78.8 48.3 97.7

84 35.3 48.1 95.3 0.7 53.7 21.2 51.7 2.3

48 52 22 22 45 39 62 80 7 18 10 96.3 15 13 46 33 46 80 10 25 10.5 29 13

52 48 78 78 55 61 38 20 93 82 90 3.7 85 87 54 67 54 20 90 75 89.5 71 87

Solvent: thiophene Methylcyclopentane Cyclohexane Hexane Heptane 2,3-Dimethylpentane 2,4-Dimethylpentane

71.5 77.9 68.5 83.1 80.9 76.6 Solvent: benzene

Methylcyclopentane Cyclohexene Cyclohexane Hexane Heptane 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 2,2,4-Trimethylpentane

71.7 78.9 77.6 68.5 80.1 75.9 79.4 75.2 80.1 Solvent: bis(2-hydroxyethyl) ether

Biphenyl Diphenylmethane 1,3,5-Trimethylbenzene Naphthalene 1-Methylnaphthalene 2-Methylnaphthalene Acenaphthene Fluorene Benzyl acetate Bornyl acetate Ethyl fumarate Dimethyl o-phthalate Methyl salicylate 2-Hydroxy-1-isopropyl-4-methylbenzene 1,2-Dihydroxybenzene Safrole Isosafrole Benzyl phenyl ether Nitrobenzene m-Nitrotoluene o-Nitrophenol Quinoline p-Dibromobenzene

232.7 236.0 210.0 212.6 277.0 225.5 239.6 243.0 214.9 223.0 217.1 245.4 220.6 232.3 259.5 225.5 233.5 241.5 210.0 224.2 216.0 233.6 212.9

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.77

PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.12 Ternary Azeotropic Mixtures A. Ternary azeotropes containing water and alcohols Composition, wt %

System

BP of azeotrope, ⬚C

Alcohol

Other component

1.3 0.6 6.3

8.2 5.4 81.2

90.5 94.0 13.5

1 8.7 7.4 7.5 6.3 1.6 4.5 2.3 4.8 4.8 5 11.4 12.1 9.0 6.1 3 12 5.5 9

55 20.3 18.5 42.5 8.6 5.0 10.0 3.5 87.9 19.7 17 27.6 18.4 8.4 33.0 12 37 16.1 13

44 71.0 74.1 50.0 85.1 93.4 85.5 94.2 7.3 75.5 78 61.0 69.5 82.6 60.9 85 51 78.4 78

10.1 11 10.0 51.6 44.8 20.2 20 10.0 5 20.7

82.3 84 81.5 21.0 47.2 68.1 60 73.0 82 66.8

18.7 40.5

73.8 47.0

Water Methanol

Chloroform 2-Methyl-1,3-butadiene Methyl chloroacetate

52.3 30.2 67.9 Ethanol

Acetonitrile Acrylonitrile Benzene Butylamine Butyl methyl ether Carbon disulfide Carbon tetrachloride Chloroform Crotonaldehyde Cyclohexane 1,2-Dichloroethane 1,1-Diethoxyethane Diethoxymethane Ethyl acetate Heptane Hexane Toluene Trichloroethylene Triethylamine

72.9 69.5 64.9 81.8 62 41.3 62 55.3 78.0 62.6 66.7 77.8 73.2 70.2 68.8 56.0 74.4 67.0 74.7

1-Propanol Benzene Carbon tetrachloride Cyclohexane 1,1-Dipropoxyethane Dipropoxymethane Dipropyl ether 3-Pentanone Propyl acetate Propyl formate Tetrachloroethylene

67 65.4 66.6 87.6 86.4 74.8 81.2 82.5 70.8 81.2

7.6 5 8.5 27.4 8.0 11.7 20 17.0 13 12.5 2-Propanol

Benzene Butylamine

66.5 83

7.5 12.5

short standard long

DEAN #37261

LEFT

(McGHP)

5.78

INTERACTIVE

top of rh base of rh

SECTION 5

cap height base of text

TABLE 5.12 Ternary Azeotropic Mixtures (Continued) Composition, wt %

System

BP of azeotrope, ⬚C

Water

Alcohol

Other component

18.5 38.2 20

74.0 48.7 73

27.4 10.0 34.6 7.6 2.9 18.3 14.6

35.3 68.7 35.5 51.0 77.9 11.8 25.4

4.95 10.8 19

91.00 80.3 72

23.1 6.7 16.4

46.5 76.0 65.7

21.4 11.9 21

70.5 85.0 71

31.2 19.6

24.0 48.0

9.2 11 11 5.1

82.2 84 81 86.4

2-Propanol (continued) Cyclohexane Toluene Trichloroethylene

64.3 76.3 69.4

7.5 13.1 7 1-Butanol

Butyl acetate Butyl formate Dibutyl ether Heptane Hexane Nonane Octane

89.4 83.6 90.6 78.1 61.5 90.0 86.1

37.3 21.3 29.9 41.4 19.2 69.9 60.0 2-Butanol

Carbon tetrachloride Cyclohexane Isooctane

65 69.7 76.3

4.05 8.9 9 2-Methyl-1-propanol

Isobutyl acetate Isobutyl formate Toluene

86.8 80.2 81.3

30.4 17.3 17.9 2-Methyl-2-propanol

Benzene Carbon tetrachloride Cyclohexane

67.3 64.7 65.0

8.1 3.1 8 3-Methyl-1-butanol

Isopentyl acetate Isopentyl formate

93.6 89.8

44.8 32.4 Allyl alcohol

Benzene Carbon tetrachloride Cyclohexane Hexane

68.2 65.2 66.2 59.7

8.6 5 8 8.5

short standard long

B. Other ternary azeotropes Composition, wt %

BP of azeotrope, ⬚C

Composition, wt %

Water Acetone 2-Methyl-1,3-butadiene

32.5

0.4 7.6 92.0

Water Nitromethane Heptane

71.4

7.9 29.7 62.4

Water Acetonitrile Benzene

66

8.2 23.3 68.5

Water Nitromethane Nonane

80.7

17.4 58.3 24.3

Water Acetonitrile Trichloroethylene

67

6.4 20.5 73.1

Water Nitromethane Octane

77.4

12.4 44.3 43.3

Water Acetonitrile Triethylamine

68.6

3.5 9.6 86.9

Water Nitromethane Pentane

33.1

2.1 6.5 91.4

Water 2-Butanone Cyclohexane

63.6

5 35 60

Water Nitromethane Undecane

82.8

20.6 73.3 6.1

Water Butyraldehyde Hexane

55.0

4 21 75

Water Pyridine Dodecane

93.5

40.5 54.5 5.0

System

21.3 76.3 2.4

Water Pyridine Undecane

93.1

38.5 51.0 10.5

Water Formic acid Isobutyric acid

107.0

15.5 66.8 17.7

Water Pyridine Decane

92.3

35.5 45.5 19.0

5.79

INTERACTIVE

107.6

RIGHT

Water Formic acid Isopentanoic acid

(McGHP)

BP of azeotrope, ⬚C

System

DEAN #37261

TABLE 5.12 Ternary Azeotropic Mixtures (Continued)

top of page

short standard

base of DF

Composition, wt %

BP of azeotrope, ⬚C

Composition, wt %

Water Formic acid Butyric acid

107.6

19.5 75.9 4.6

Water Pyridine Nonane

90.5

30.5 37.0 32.5

Water Formic acid Propionic acid

107.2

18.6 71.9 9.5

Water Pyridine Octane

86.7

22.4 25.5 52.0

Water Hydrogen bromide Chlorobenzene

105

11.0 10.4 78.6

Water Pyridine Heptane

78.6

14.0 15.5 70.5

System

96.9

20.2 5.3 74.5

Acetic acid Pyridine Acetic anhydride

134.4

23 55 22

Water Hydrogen chloride Phenol

107.3

64.8 15.8 19.4

Acetic acid Pyridine Decane

134.1

31.4 38.2 30.4

Water Hydrogen fluoride Fluorosilic acid

116.1

54 10 36

Acetic acid Pyridine Ethylbenzene

129.1

13.5 25.2 61.3

75.1

11.5 75.1 64.0

Acetic acid Pyridine Heptane

98.5

3.4 10.6 86.0

Water Nitroethane Hexane

59.5

8.4 9.3 82.3

Acetic acid Pyridine Nonane

128.0

20.7 29.4 49.9

Water Nitromethane Decane

82.4

19.1 68.1 12.8

Acetic acid Pyridine Octane

115.7

10.4 20.1 69.5

INTERACTIVE

Water Nitroethane Heptane

LEFT

Water Hydrogen chloride Chlorobenzene

(McGHP)

BP of azeotrope, ⬚C

System

DEAN #37261

TABLE 5.12 Ternary Azeotropic Mixtures (Continued)

5.80

top of page

short standard

base of DF

TABLE 5.12 Ternary Azeotropic Mixtures (Continued) BP of azeotrope, ⬚C

Composition, wt %

83.1

21.5 75.3 3.2

Acetic acid Pyridine o-Xylene

132.2

17.7 30.5 51.8

Acetic acid Pyridine p-Xylene

129.2

10.2 22.5 67.3

Methanol Methyl acetate Hexane

47.4

14.6 36.8 48.6

Acetic acid 2,6-Dimethylpyridine Undecane

163.0

75.0 13.8 11.2

Ethanol Acetone Chloroform

63.2

10.4 24.3 65.3

Acetic acid 2,6-Dimethylpyridine Decane

147.0

12.6 74.3 13.1

Ethanol Acetonitrile Triethylamine

70.1

8 34 58

Acetic acid 2-Methylpyridine Decane

141.3

19.9 46.8 33.3

Ethanol Benzene Cyclohexane

64.7

29.6 12.8 57.6

Acetic acid 2-Methylpyridine Nonane

135.0

12.8 38.4 48.8

Ethanol Chloroform Hexane

57.3

9.5 56.1 34.4

Acetic acid 2-Methylpyridine Octane

121.3

3.6 24.8 71.6

1-Propanol Benzene Cyclohexane

73.8

15.5 30.4 54.2

77.2

7.6 34.4 58.0

2-Propanol Benzene Cyclohexane

69.1

31.1 15.0 53.9

77.4

4 48 48

Water Nitromethane Dodecane

132

15 54 31

1-Butanol Benzene Cyclohexane

Propionic acid 2-Methylpyridine Decane

149.3

29.5 32.0 38.5

1-Butanol Pyridine Toluene

108.7

INTERACTIVE

Acetic acid 2-Methyl-1-butanol Isopentyl acetate

RIGHT

Acetic acid Benzene Cyclohexane

System

(McGHP)

Composition, wt %

DEAN #37261

BP of azeotrope, ⬚C

System

11.9 20.7 76.4

5.81

top of page

short standard

base of DF

Composition, wt %

BP of azeotrope, ⬚C

Composition, wt %

Propionic acid 2-Methylpyridine Nonane

140.1

16.5 21.5 42.0

1,2-Ethanediol Phenol 2,6-Dimethylpyridine

185.0

8.7 74.6 16.7

Propionic acid 2-Methylpyridine Octane

123.7

4.5 10.5 85.0

1,2-Ethanediol Phenol 2-Methylpyridine

185.1

5.9 79.1 15.0

Propionic acid 2-Methylpyridine Undecane

153.4

43.0 40.0 17.0

1,2,-Ethanediol Phenol 3-Methylpyridine

186.4

15.9 67.7 16.4

Propionic acid Pyridine Undecane

147.1

55.5 26.4 18.1

1,2-Ethanediol Phenol 2,4,6-Trimethylpyridine

188.6

29.5 54.8 15.7

System

57.5

23 30 47

Acetone Chloroform Hexane

60.8

3.6 68.8 27.6

Methanol Acetone Hexane

47

14.6 30.8 59.6

Acetone Methyl acetate Hexane

49.7

51.1 5.6 43.3

Methanol Acetone Methyl acetate

53.7

17.4 5.8 76.8

Chloroform Ethyl formate 2-Bromopropane

62.0

79.7 5.3 15.7

Methanol Methyl acetate Cyclohexane

50.8

17.8 48.6 33.6

1,4-Dioxane 2-Methyl-1-propanol Toluene

101.8

44.3 26.7 29.0

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FREEZING MIXTURES

TABLE 5.13 Compositions of Aqueous Antifreeze Solutions Freezing point of ethyl alcohol-water mixtures* Freezing point Specific gravity 20⬚/4⬚C. (68⬚F.)

% alcohol by weight

% alcohol by volume

⬚C.

⬚F.

0.99363 0.98971 0.98658 0.98006 0.97670 0.97336 0.97194 0.97024 0.96823 0.96578 0.96283 0.95914 0.95400 0.94715 0.93720 0.92193 0.90008 0.86311

2.5 4.8 6.8 11.3 13.8 16.4 17.5 18.8 20.3 22.1 24.2 26.7 29.9 33.8 39.0 46.3 56.1 71.9

3.13 6.00 8.47 14.0 17.0 20.2 21.5 23.1 24.8 27.0 29.5 32.4 36.1 40.5 46.3 53.8 63.6 78.2

⫺1.0 ⫺2.0 ⫺3.0 ⫺5.0 ⫺6.1 ⫺7.5 ⫺8.7 ⫺9.4 ⫺10.6 ⫺12.2 ⫺14.0 ⫺16.0 ⫺18.9 ⫺23.6 ⫺28.7 ⫺33.9 ⫺41.0 ⫺51.3

30.2 28.4 26.6 23.0 21.0 18.5 16.3 15.1 12.9 10.0 6.8 3.2 ⫺2.0 ⫺10.5 ⫺19.7 ⫺29.0 ⫺41.8 ⫺60.3

Freezing point of methyl (wood) alcohol-water mixtures* Freezing point Specific gravity 15.6⬚C. (60⬚F.)

% alcohol by weight

% alcohol by volume

⬚C.

⬚F.

0.993 0.986 0.980 0.974 0.968 0.963 0.956 0.949 0.942

3.9 8.1 12.2 16.4 20.6 24.9 29.2 33.6 38.0

5 10 15 20 25 30 35 40 45

⫺2.2 ⫺5.0 ⫺8.3 ⫺11.7 ⫺15.6 ⫺20.0 ⫺25.0 ⫺30.0 ⫺35.6

28 23 17 11 4 ⫺4 ⫺13 ⫺22 ⫺32

* Values are for pure alcohol. Since some commercial antifreezes contain small amounts of water, slightly higher volume concentrations than those given in the table may be required. Antifreezes also contain corrosion inhibitors and other additives to make them function properly as cooling liquids. These affect freezing point slightly and specific gravity to a greater degree. If a protection table is furnished by the manufacturer it should be used in preference to the values given above for the pure substance.

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TABLE 5.13 Compositions of Aqueous Antifreeze Solutions (Continued) Freezing point of Prestone-water mixtures† % Prestone

Specific gravity

Freezing point

By weight

By volume

15⬚/15C. (59⬚F.)

⬚C.

⬚F.

10 15 20 25 30 40 50 60

9.2 13.8 18.3 23.0 28.0 37.8 47.8 58.1

1.013 1.019 1.026 1.033 1.040 1.053 1.067 1.079

⫺3.6 ⫺5.6 ⫺7.9 ⫺10.7 ⫺14.0 ⫺22.3 ⫺33.8 ⫺49.3

25.6 22.0 17.8 12.8 6.8 ⫺8.2 ⫺28.8 ⫺56.7

Freezing point of ethyl alcohol-water mixtures Freezing point Specific gravity 15.6⬚C. (60⬚F.)

% alcohol by volume

⬚C.

⬚F.

0.990 0.984 0.978 0.972 0.964 0.955 0.945 0.933 0.922 0.910 0.899 0.887 0.875 0.864 0.852 0.840

5 10 15 20 25 30 35 40 45 50 55 60 65 70 75 80

⫺1.7 ⫺3.3 ⫺6.1 ⫺8.3 ⫺11.1 ⫺14.4 ⫺17.8 ⫺18.3 ⫺18.9 ⫺20.0 ⫺21.7 ⫺23.3 ⫺24.4 ⫺26.7 ⫺32.2 ⫺41.7

29 26 21 17 12 6 0 ⫺1 ⫺2 ⫺4 ⫺7 ⫺10 ⫺12 ⫺16 ⫺26 ⫺43

† Eveready Prestone marketed for antifreeze purposes, is 97% ethylene glycol containing fractional percentages of soluble and insoluble ingredients to prevent foaming, creepage and water corrosion in automobile cooling systems.

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TABLE 5.13 Compositions of Aqueous Antifreeze Solutions (Continued) Freezing point of propylene glycol-water mixtures* Freezing point Specific gravity 15.6⬚C. (60⬚F.)

% glycol by volume

⬚C.

⬚F.

1.004 1.006 1.012 1.017 1.020 1.024 1.028 1.032 1.037 1.040

5 10 15 20 25 30 35 40 45 50

⫺1.1 ⫺2.2 ⫺3.9 ⫺6.7 ⫺8.9 ⫺12.8 ⫺16.1 ⫺20.6 ⫺26.7 ⫺33.3

30 28 25 20 16 9 3 ⫺5 ⫺16 ⫺28

Freezing point of glycerol-water mixtures† Freezing point % Glycerol by weight

Specific gravity 15⬚/15⬚C. (59⬚F.)

Specific gravity 20⬚/20⬚C. (68⬚F.)

⬚C.

⬚F.

10 20 30 40 50 60 70 80 90 100

1.02415 1.04935 1.07560 1.10255 1.12985 1.15770 1.18540 1.21290 1.23950 1.26557

1.02395 1.04880 1.07470 1.10135 1.12845 1.15605 1.18355 1.21090 1.23755 1.26362

⫺1.6 ⫺4.8 ⫺9.5 ⫺15.5 ⫺22.0 ⫺33.6 ⫺37.8 ⫺19.2 ⫺1.6 17.0

29.1 23.4 14.9 4.3 ⫺7.4 ⫺28.5 ⫺36.0 ⫺2.3 29.1 62.6

* Values are for pure alcohol. Since some commercial antifreezes contain small amounts of water, slightly higher volume concentrations than those given in the table may be required. Antifreezes also contain corrosion inhibitors and other additives to make them function properly as cooling liquids. These affect freezing point slightly and specific gravity to a greater degree. If a protection table is furnished by the manufacturer it should be used in preference to the values given above for the pure substance. † The values are those reported by Bosart and Snoddy (Jour. Ind. Eng. Chem., 19, 506 (1927)), and Lane (Jour. Ind. Eng. Chem., 17, 924 (1925)) but modified by adding 2⬚F to all temperatures below 0⬚F in accordance with the suggestion of the Procter and Gamble Co.

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TABLE 5.13 Compositions of Aqueous Antifreeze Solutions (Continued) Freezing point of magnesium chloride brines Freezing point % MgCl2 by weight

Spec. grav. 15.6⬚C. (60⬚F.)

⬚C.

5 6 7 8 9 10 11 12 13 14 15 16 17

1.043 1.051 1.060 1.069 1.078 1.086 1.096 1.105 1.114 1.123 1.132 1.142 1.151

⫺3.11 ⫺3.89 ⫺4.72 ⫺5.67 ⫺6.67 ⫺7.83 ⫺9.05 ⫺10.5 ⫺12.1 ⫺13.7 ⫺15.6 ⫺17.6 ⫺19.7

Freezing point

⬚F.

% MgCl2 by weight

Spec. grav. 15.6⬚C. (60⬚F.)

⬚C.

⬚F.

26.4 25.0 23.5 21.8 20.0 17.9 15.7 13.1 10.3 7.3 4.0 0.4 ⫺3.5

18 19 20 21 22 23 24 25 26 27 28 29 30

1.161 1.170 1.180 1.190 1.200 1.210 1.220 1.230 1.241 1.251 1.262 1.273 1.283

⫺22.1 ⫺25.6 ⫺27.4 ⫺30.6 ⫺32.8 ⫺28.9 ⫺25.6 ⫺23.3 ⫺21.1 ⫺19.4 ⫺18.3 ⫺17.2 ⫺16.7

⫺7.7 ⫺12.2 ⫺17.3 ⫺23.0 ⫺27.0 ⫺20.0 ⫺14.0 ⫺10.0 ⫺6.0 ⫺3.0 ⫺1.0 ⫹1.0 2.0

Freezing point of sodium chloride brines Compiled in collaboration with C. D. Looker, Ph.D., International Salt Co., Inc. Freezing point % NaCl by weight

Spec. grav. 15⬚C. (59⬚F.)

⬚C.

⬚F.

0 1 2 3 4 5 6 7 8 9 10 11 12 13 14

1.000 1.007 1.014 1.021 1.028 1.036 1.043 1.051 1.059 1.067 1.074 1.082 1.089 1.097 1.104

0.00 ⫺0.58 ⫺1.13 ⫺1.72 ⫺2.35 ⫺2.97 ⫺3.63 ⫺4.32 ⫺5.03 ⫺5.77 ⫺6.54 ⫺7.34 ⫺8.17 ⫺9.03 ⫺9.94

32.0 31.0 30.0 28.9 27.8 26.7 25.5 24.2 22.9 21.6 20.2 18.8 17.3 15.7 14.1

Freezing point % NaCl by weight 15 16 17 18 19 20 21 22 23 23.3 (E) 24 25 26 26.3

Spec. grav. 15⬚C. (59⬚F.)

⬚C.

⬚F.

1.112 1.119 1.127 1.135 1.143 1.152 1.159 1.168 1.176 1.179 1.184 1.193 1.201 1.203

⫺10.88 ⫺11.90 ⫺12.93 ⫺14.03 ⫺15.21 ⫺16.46 ⫺17.78 ⫺19.19 ⫺20.69 ⫺21.13 ⫺17.0* ⫺10.4* ⫺2.3* 0.0*

12.4 10.6 8.7 6.7 4.6 2.4 ⫹0.0 ⫺2.5 ⫺5.2 ⫺6.0 ⫹1.4* 13.3* 27.9* 32.0*

* Saturation temperatures of sodium chloride dihydrate; at these temperatures NaCl · 2H2O separates leaving the brine of the eutectic composition (E).

5.4.1

Propylene Glycol– Glycerol

Propylene glycol, a satisfactory antifreeze with the advantage of being nontoxic, can be combined with glycerol, also an efficient nontoxic antifreeze, to give a mixture that can be tested for freezing point with an ethylene glycol (Prestone) hydrometer. A mixture of 70% propylene glycol and 30% glycerol (% by weight of water-free materials), when diluted, can be tested on the standard instrument used for ethylene glycol solutions.

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DENSITY AND SPECIFIC GRAVITY

TABLE 5.14 Density of Mercury and Water The density of mercury and pure air-free water under a pressure of 101 325 Pa(1 atm) is given in units of grams per cubic centimeter (g · cm⫺3). For mercury, the values are based on the density at 20⬚C being 13.545 884 g · cm⫺3. Water attains its maximum density of 0.999 973 g · cm⫺3 at 3.98⬚C. For water, the temperature (tm, ⬚C) of maximum density at different pressures (p) in atmospheres is given by tm ⫽ 3.98 ⫺ 0.0225(p ⫺ 1) Density of water

0.999 0.999 0.999 0.999 0.999 0.999 0.999 0.999 0.998 0.998 0.998 0.997 0.997 0.996 0.996 0.995 0.995 0.994 0.993 0.992 0.992 0.991 0.990 0.989 0.988 0.988

84 94 97 94 85 70 50 24 94 60 20 77 30 78 23 65 03 37 69 97 22 44 63 79 93 04

Temp., ⬚C

Density of mercury

Density of water

⫺20 ⫺18 ⫺16 ⫺14 ⫺12 ⫺10 ⫺8 ⫺6 ⫺4 ⫺2 0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40 42 44 46 48 50

13.644 59 13.639 62 13.634 66 13.629 70 13.624 75 13.619 79 13.614 85 13.609 90 13.604 96 13.600 02 13.595 08 13.590 15 13.585 22 13.580 29 13.575 36 13.570 44 13.565 52 13.560 60 13.555 70 13.550 79 13.545 88 13.540 97 13.536 06 13.531 17 13.526 26 13.521 37 13.516 47 13.511 58 13.506 70 13.501 82 13.496 93 13.492 07 13.487 18 13.482 29 13.477 42 13.472 56

0.987 0.986 0.985 0.984 0.983 0.982 0.981 0.980 0.978 0.977 0.976 0.975 0.974 0.973 0.971 0.970 0.969 0.967 0.966 0.965 0.963 0.962 0.961 0.959 0.958

12 18 21 22 20 16 09 01 90 77 61 44 24 03 79 53 26 96 65 31 96 59 20 79 36

Temp., ⬚C

Density of mercury

52 54 56 58 60 62 64 66 68 70 72 74 76 78 80 82 84 86 88 90 92 94 96 98 100 120 140 160 180 200 220 240 260 280 300

13.467 68 13.462 82 13.457 96 13.453 09 13.448 23 13.443 37 13.438 52 13.433 67 13.428 82 13.423 97 13.419 13 13.414 28 13.409 43 13.404 60 13.399 77 13.394 92 13.390 09 13.385 26 13.380 42 13.375 60 13.370 77 13.365 94 13.361 12 13.356 30 13.351 48 13.303 4 13.255 4 13.207 6 13.159 8 13.112 0 13.064 5 13.016 9 12.969 2 12.921 5 12.873 7

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TABLE 5.15 Specific Gravity of Air at Various Temperatures The table below gives the weight in grams ⫻ 104 of 1 mL of air at 760 mm of mercury pressure and at the temperature indicated. Density in grams per milliliter is the same as the specific gravity referred to water at 4⬚C as unity. To convert to density referred to air at 70⬚F as unity, divide the values below by 12.00. t⬚C.

Sp.Gr. ⫻ 104

t⬚C.

Sp.Gr. ⫻ 104

t⬚C.

Sp.Gr. ⫻ 104

t⬚C.

Sp.Gr. ⫻ 104

⫺25 ⫺24 ⫺23 ⫺22 ⫺21

14.240 14.182 14.125 14.069 14.013

15 16 17 18 19

12.255 12.213 12.170 12.129 12.087

60 62 64 66 68

10.596 10.532 10.470 10.408 10.347

140 142 144 146 148

8.541 8.500 8.459 8.419 8.379

⫺20 ⫺19 ⫺18 ⫺17 ⫺16

13.957 13.902 13.847 13.793 13.739

20 21 22 23 24

12.046 12.004 11.964 11.923 11.883

70 72 74 76 78

10.286 10.227 10.168 10.109 10.052

150 155 160 165 170

8.339 8.242 8.147 8.054 7.963

⫺15 ⫺14 ⫺13 ⫺12 ⫺11

13.685 13.632 13.580 13.527 13.476

25 26 27 28 29

11.843 11.803 11.764 11.725 11.686

80 82 84 86 88

9.995 9.938 9.882 9.828 9.773

175 180 185 190 195

7.874 7.787 7.702 7.619 7.537

⫺10 ⫺9 ⫺8 ⫺7 ⫺6

13.424 13.373 13.322 13.272 13.222

30 31 32 33 34

11.647 11.609 11.570 11.533 11.495

90 92 94 96 98

9.719 9.666 9.613 9.561 9.509

200 205 210 215 220

7.457 7.379 7.303 7.228 7.155

⫺5 ⫺4 ⫺3 ⫺2 ⫺1

13.173 13.124 13.075 13.026 12.978

35 36 37 38 39

11.458 11.420 11.383 11.347 11.310

100 102 104 106 108

9.458 9.408 9.358 9.308 9.259

230 240 250 260 270

7.013 6.881 6.753 6.624 6.504

0 ⫹1 2 3 4

12.931 12.883 12.836 12.790 12.743

40 41 42 43 44

11.274 11.238 11.202 11.167 11.132

110 112 114 116 118

9.211 9.163 9.116 9.069 9.022

280 290 300 310 320

6.389 6.277 6.166 6.062 5.942

5 6 7 8 9

12.697 12.652 12.606 12.561 12.517

45 46 47 48 49

11.097 11.062 11.027 10.993 10.958

120 122 124 126 128

8.976 8.931 8.886 8.841 8.797

330 340 350 360 370

5.847 5.755 5.664 5.578 5.493

10 11 12 13 14

12.472 12.428 12.385 12.341 12.298

50 52 54 56 58

10.924 10.857 10.791 10.725 10.660

130 132 134 136 138

8.753 8.710 8.667 8.625 8.583

380 400 420 440 460

5.407 5.248 5.101 4.952 4.812

5.5.1

Density of Moist Air

The density of moist air depends upon the temperature, the humidity, and the barometric pressure. It is expressed by the equation

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d t ⫽ Dt ⫻

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P ⫺ 0.3783e 760

where d t is the density of the moist air at the temperature t; Dt is the density of dry air at the temperature t (see Table 5.15, Specific Gravity of Air at Various Temperatures); P is the height of the barometer after correction and reduction to standard conditions, and is expressed in millimeters of mercury (see Sec. 2.1.3, Barometry and Barometric Corrections); e is the vapor pressure of water at the temperature of the dew point and is expressed in millimeters of mercury (see Table 5.6, Vapor Pressure of Water). Example. To find the density of moist air at a temperature of 20⬚C, with a dew point of 10⬚C, and a corrected barometric pressure of 750 mm. Reference to Table 5.15 shows that D at 20⬚C is equal to 0.001 204 6 g/mL. Reference to Table 5.6 shows that at 10⬚C (the temperature of the dew point) e is equal to 9.209 mm. Therefore, d ⫽ 0.001 204 6 ⫻

750 ⫺ (0.3783 ⫻ 9.209) 760

⫽ 0.001 183 2 g/mL ⫽ 1.1832 g/L 5.5.2 5.5.2.1

Specific Gravity Corrections for the Buoyant Effect of Air Determinations Made with a Pyknometer

冉 冊 冉 冊

Dvac ⫽

W2 W2d d ⫺ 0.0012 ⫺1 W1 W1

Svac ⫽

W2 W2 ⫺ 0.0012 ⫺1 W1 W1

where Dvac ⫽ density of the liquid in grams per milliliter at t⬚C corrected for the buoyant effect of air W1 ⫽ weight in air of the water required to fill the pyknometer at t⬚C W2 ⫽ weight in air of the liquid required to fill the pyknometer at t⬚C d ⫽ density of water in grams per milliliter at t⬚C Svac ⫽ specific gravity of the liquid at t⬚C referred to water at t⬚C corrected for the buoyant effect of air When the weight of the water is determined at a temperature of t⬚C, and that of the liquid at a different temperature t⬘, the equations above are modified as follows:

冉

冊

Dvac ⫽

W2 W2 d ⫺ 0.0012 d⫺1 W1 W1

Svac ⫽

W2 W2 ⫺ 0.0012 ⫺1 W1 W1

冉

冊

冉 冊 冉 冊

⫹ 0.000 026 (t⬘ ⫺ t⬚)

⫹ 0.000 026 (t⬘ ⫺ t⬚)

W2 d W1

W2 d W1

5.5.2.2 Determinations Made with a Plummet or Sinker. The equations above may also be used when the density is determined with plummet or sinker, but in this case W1 ⫽ weight of the plummet in air minus its weight in water W2 ⫽ weight of the plummet in air minus its weight in the liquid

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VISCOSITY, SURFACE TENSION, DIELECTRIC CONSTANT, DIPOLE MOMENT, AND REFRACTIVE INDEX

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances For the majority of substances the dependence of the surface tension ␥ on the temperature can be given as:

␥ ⫽ a ⫺ bt where a and b are constants and t is the temperature in degrees Celsius. In the SI system the surface tensions are expressed in mN · m⫺1 (⫽ dyn · cm⫺1). A compilation of some 2200 liquid compounds has been prepared by J. J. Jasper, J. Phys. Chem. Reference Data 1:841 (1972). The SI unit of viscosity is pascal-second (Pa · s) or newton-second per meter squared (N · s · m⫺2). Values tabulated are mN · s · m⫺2 (⫽ centipoise, cP). The temperature in degrees Celsius at which the viscosity of a substance was measured is shown in parentheses after the value. Surface tension, mN · m⫺1 Substance

a

b

Acetaldehyde Acetaldoxime

23.90 34.23

0.1360 0.1134

Acetamide Acetanilide Acetic acid Acetic anhydride Acetone Acetonitrile Acetophenone Acetyl chloride Acrylic acid Acrylonitrile Allyl acetate Allyl alcohol Allylamine Allyl isothiocyanate 2-Aminoethanol Aniline Benzaldehyde Benzamide Benzene Benzenesulfonyl chloride Benzenethiol Benzonitrile Benzophenone Benzoyl bromide Benzoyl chloride Benzyl alcohol Benzylamine Benzyl benzoate Benzyl chloride

47.66 46.21 29.58 35.52 26.26 29.58 41.92 26.7(15) 28.1(30) 29.58 28.73 27.53 27.49 36.76 51.11 44.83 40.72 47.26 28.88(20) 45.48 41.41 41.69 46.31 45.85 41.34 38.25 42.33 48.07 39.92

0.1021 0.0912 0.0994 0.1436 0.112 0.1178 0.1154

0.1178 0.1186 0.0902 0.1287 0.1074 0.1117 0.1085 0.1090 0.0705 27.56(30) 0.1117 0.1202 0.1159 0.1128 0.1397 0.1084 0.1381 0.1213 0.1065 0.1227

Liquid range, ⬚C ⫺123 to 21 12(␤) or 46.5(␣) to 114.5 81 to 222 114 to 304 16.7 to 118 ⫺73 to 139 ⫺94 to 56 ⫺44 to 81.6 20 to 202 ⫺113 to 51 14 to 141 ⫺83.5 to 77.3 up to 104 ⫺129 to 97 ⫺88 to 55 ⫺80 to 152 10.3 to 171 ⫺6 to 186 ⫺26 to 179 129 to 290 5.5 to 80 14.5 to 251 ⫺14.9 to 169 ⫺12.7 to 191 48 to 305 ⫺24 to 219 ⫺1 to 197 ⫺15.2 to 205 10 to 180 21 to 323 ⫺43 to 179

Viscosity, mN · s · m⫺2 0.2797(0), 0.2557(10), 0.22(20)

1.63(94), 1.32(105), 1.06(120) 2.22(120), 1.90(130) 1.056(25), 0.786(50), 0.424(110) 1.241(0), 0.907(20), 0.699(40) 0.395(0), 0.306(25), 0.256(50) 0.397(10), 0.329(30), 0.2753(50) 1.511(30), 1.192(45), 0.634(100) 0.368(25), 0.294(50)

1.218(25), 0.759(50), 0.553(70)

3.847(25), 2.029(50), 1.247(75)

0.649(20), 0.566(30), 0.395(60)

1.447(15), 1.111(30), 0.883(50)

5.474(25), 2.760(50), 1.618(75) 1.624(25), 1.080(50), 0.769(75) 8.454(25)

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TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

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Surface tension, mN · m⫺1 Substance Benzyl ethyl ether Biphenyl Bis(2-ethoxyethyl) ether Bis(2-hydroxyethyl) ether Bis(2-methoxyethyl) ether Bromobenzene 1-Bromobutane (⫾)-2-Bromobutane Bromochloromethane Bromocyclohexane 1-Bromodecane Bromodichloromethane 1-Bromododecane Bromoethane Bromoform 1-Bromoheptane 1-Bromohexadecane 1-Bromohexane Bromomethane 1-Bromo-3-methylbutane 1-Bromo-2-methylpropane 1-Bromonaphthalene 1-Bromononane 1-Bromooctane 1-Bromopentane p-Bromophenol 1-Bromopropane 2-Bromopropane 3-Bromopropene 1-Bromotetradecane o-Bromotoluene p-Bromotoluene 1-Bromoundecane Butanal Butane 1,3-Butanediol 2,3-Butanediol Butanenitrile Butanesulfonyl chloride 1-Butanethiol Butanoic acid Butanoic anhydride 1-Butanol (⫾)-2-Butanol 2-Butanone 1-Butene 2-Butene 3-Butenenitrile 2-Butoxyethanol

a

b

Liquid range, ⬚C

32.82(20) 41.52 29.74 46.97 32.47 38.14 28.71 27.48 33.32(20) 36.13 31.26 35.11 32.58 26.52 48.14 30.74 33.37 29.81 26.52 28.10 26.96 46.44 31.36 31.00 29.51 48.88 28.30 26.21 29.45 32.93 36.62 36.40 31.94 26.67 14.87 37.8(25) 36(25)

29.97(40) 0.0931 0.1176 0.0880 0.1164 0.1160 0.1126 0.1107

up to 186 69 to 256 ⫺45 to 188 ⫺10.4 to 246 ⫺68 to 162 ⫺30.6 to 156 ⫺112.4 to 101.6 ⫺112.7 to 91.4 ⫺88 to 68 up to 165.8 ⫺30 to 240 ⫺55 to 87 ⫺11 to bp ⫺119 to 38.2 8 to 149 ⫺58 to 180 17.8 to 336 ⫺85 to 158 ⫺94 to 3.56 ⫺112 to 119.7 ⫺119 to 91.5 ⫺1.8 to 281 ca. ⫺55 to 201 ⫺55 to 201 ⫺88 to 129.6 64 to 238 ⫺110.1 to 71 ⫺89 to 59.5 ⫺119 to 70 6 to ⬎178 ⫺26 to 181 28.5 to 184 ⫺9 to ⬎138 ⫺99 to 74.8 ⫺138.3 to ⫺0.5 ⬍⫺50 to 207.5 25 to 182 ⫺112 to 117.6

37.33 28.07 28.35 28.93(20) 27.18 23.47(20) 26.77 15.19 16.11 31.40 28.18

0.1117 0.0856 0.1294 0.0882 0.1159 0.1308 0.0982 0.0861 0.0967 0.1159 0.0996 0.1059 0.1018 0.0894 0.0928 0.1049 0.1070 0.1218 0.1183 0.1257 0.0878 0.0998 0.0997 0.0861 0.0925 0.1206

0.0977 0.1142 0.0920 28.44(25) 0.0898 22.62(30) 0.1122 0.1323 0.1289 0.1085 0.0816

⫺116 to 98.5 ⫺6 to 163.5 ⫺66 to 199.5 ⫺89.5 to 117.7 ⫺114.7 to 99.5 ⫺86.7 to 79.6 ⫺185 to ⫺6.5 ⫺106 to 0.9 ⫺87 to 119 ⫺75 to 168

Viscosity, mN · s · m⫺2

1.196(15), 0.985(30), 0.385(1423) 0.633(20), 0.606(25), 0.471(50)

0.477(10), 0.374(25)

0.539(15), 0.459(30), 0.338(70) 0.536(15), 0.437(30), 0.359(50) 0.620(0), 0.471(25), 0.373(50)

0.553(25), 0.418(50), 0.330(75)

1.540(20), 0.980(40), 0.323(60) 5.185(0), 2.948(20), 1.782(40) 3.907(20), 1.332(50), 0.698(75) 0.428(20), 0.349(40), 0.249(75)

short standard long

DEAN #37261

LEFT

(McGHP)

5.92

INTERACTIVE

top of rh base of rh

SECTION 5

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

cap height base of text

Surface tension, mN · m⫺1 Substance 2-(2-Butoxyethoxy)ethanol Butyl acetate (⫾)-sec-Butyl acetate tert-Butyl acetate Butylamine sec-Butylamine tert-Butylamine Butylbenzene sec-Butylbenzene tert-Butylbenzene Butyl butanoate Butyl ethyl ether Butyl formate Butyl methyl ether Butyl nitrate Butyl propanoate 4-tert-Butylpyridine Butyl stearate Butyl vinyl ether Carbon disulfide Carbon tetrachloride D-(⫹)-Carvone Chloroacetic acid o-Chloroaniline p-Chloroaniline Chlorobenzene 1-Chlorobutane 2-Chlorobutane Chlorocyclohexane 1-Chlorododecane 1-Chloro-2,3-epoxypropane Chloroethane 2-Chloroethanol Chloroform 1-Chloroheptane 1-Chlorohexane 1-Chloro-3-methylbutane 1-Chloro-2-methylpropane 2-Chloro-2-methylpropane 1-Chloronaphthalene o-Chloronitrobenzene m-Chloronitrobenzene p-Chloronitrobenzene 1-Chlorooctane 1-Chloropentane o-Chlorophenol m-Chlorophenol p-Chlorophenol 1-Chloropropane

a 30.0(25) 27.55 23.33(22) 24.69 26.24 23.75 19.44 31.28 30.48 30.10 27.65 22.75 27.08 22.17 30.35 27.37 35.48 33.0(25) 21.99(20) 35.29 29.49 36.54 43.27 43.41 48.69 35.97 25.97 24.40 33.90 31.56 39.76 21.18(5) 38.9(20) 29.91 28.94 28.32 25.51 24.40 20.06(15) 44.12 48.10 49.71 45.84 29.64 27.09 42.5 43.7 46.0 24.41

b

0.1068 21.24(42) 0.1102 0.1122 0.1057 0.1028 0.1025 0.0979 0.0985 0.0965 0.1049 0.1026 0.1057 0.1126 0.0993 0.0951 32.7(30) 0.1484 0.1224 0.0920 0.1117 0.0904 0.1099 0.1191 0.1117 0.1118 0.1101 0.0904 0.1360 20.58(10) 0.1295 0.0961 0.1038 0.1076 0.1099 18.35(30) 0.1035 0.1171 0.1417 0.1046 0.0961 0.1076 0.1122 0.1009 0.1049 0.1246

Liquid range, ⬚C ⫺68.1 to 230.4 ⫺77 to 126 ⫺99 to 112 up to 98 ⫺50 to 77 ⫺104 to 63 ⫺66 to 44 ⫺88 to 183 ⫺82.7 to 173 ⫺58.1 to 168.5 ⫺91.5 to 166 ⫺124 to 92 ⫺91.5 to 106 ⫺115.5 to 70 up to 133 ⫺89 to 146.8 ca. ⫺44 to 197 26 to 343 ⫺92 to 94.2 ⫺111.6 to 46.5 ⫺23 to 76.7 ⬍15 to 230 61 to 189 ⫺14 to 208.8 72.5 to 232 ⫺45.3 to 131.7 ⫺123.1 to 78.4 ⫺131.3 to 68.2 ⫺44 to 142 ⫺9 to 116 ⫺57.2 to 116.1 ⫺139 to 12.3 ⫺67.5 to 128.6 ⫺63.6 to 61.1 ⫺69 to 161 ⫺104 to 99 ⫺130.3 to 68.9 ⫺26 to 50.8 ⫺2.3 to 259 33 to 246 44 to 236 84 to 242 ⫺58 to 182 ⫺99 to 108 9.8 to 175 33 to 214 43 to 220 ⫺122.8 to 47

Viscosity, mN · s · m⫺2

0.734(20), 0.688(25), 0.500(50) 0.676(25), 0.493(50), 0.370(75) 0.830(0), 0.574(25), 0.409(50) 0.770(0), 0.571(25), 0.367(50) 1.035(20), 0.683(50), 0.515(75)

0.940(0), 0.691(20), 0.472(50)

0.429(0), 0.363(20), 0.352(25) 1.321(0), 0.908(25), 0.656(50) 3.15(50), 1.92(75) 3.316(25), 1.913(50), 1.248(75) 0.799(20), 0.631(40), 0.512(60) 0.556(0), 0.422(25), 0.329(50) 0.439(15)

1.03(25) 0.416(⫺25), 0.319(0), 0.279(10) 3.913(15) 0.706(0), 0.596(15), 0.514(30)

0.462(20), 0.373(40) 0.543(15) 2.940(25)

0.580(20) 3.589(25), 1.835(50), 1.131(75) 11.55(25), 4.725(45), 4.041(50) 4.99(50) 0.436(0), 0.372(15), 0.318(30)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.93

PHYSICAL PROPERTIES

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

top of rh base of rh cap height base of text

Surface tension, mN · m⫺1 Substance 2-Chloropropane 3-Chloro-1-propene o-Chlorotoluene m-Chlorotoluene p-Chlorotoluene Chlorotrimethylsilane o-Cresol m-Cresol p-Cresol Cycloheptanol Cyclohexane Cyclohexanol Cyclohexanone Cyclohexene Cyclohexylamine Cyclooctane Cyclopentane Cyclopentanol Cyclopentanone Cyclopentene cis-Decahydronaphthalene trans-Decahydronaphthalene Decamethylcyclopentasiloxane Decamethyltetrasiloxane Decane 1-Decanol 1-Decene Dibenzylamine Dibenzyl ether p-Dibromobenzene 1,4-Dibromobutane 1,2-Dibromoethane 1,2-Dibromopropane Dibromotetrafluoroethane Dibutylamine Dibutyl decanedioate Dibutyl ether Dibutyl maleate Dibutyl o-phthalate Dichloroacetic acid o-Dichlorobenzene m-Dichlorobenzene p-Dichlorobenzene 1,4-Dichlorobutane 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene 2,2⬘-Dichloroethyl ether

a

b

21.37 25.50

0.0883 0.0946

34.93 19.51 39.43 38.00 38.58 35.02 27.62 35.33 37.67 29.23 34.19 32.02 25.53 35.04 35.55 25.94 32.18(20) 29.89(20) 19.56 86.20(25) 25.67 30.34 25.84 43.27 38.2(35) 41.84 48.24 42.85 36.81 18.9(20) 26.50

0.1082 0.0875 0.1011 0.0924 0.0962 0.0923 0.1188 0.0966 0.1242 0.1223 0.1188 0.1090 0.1462 0.1011 0.1100 0.1495 31.01(30) 28.87(30) 0.0565

24.78 32.46 33.40(20) 37.8 35.55(30) 38.30 34.66 37.79 27.03 35.43

0.0934 0.0865

0.1147 0.0879 0.1174 0.1186 0.1428

28(20) 25(20) 40.57

0.1306

0.0920 0.0732 0.0919 0.1086 0.1007 0.1190 0.1320 0.1155 18.1(25) 0.0952

0.0927

Liquid range, ⬚C ⫺117 to 36 ⫺134.5 to 45 ⫺35.6 to 159 ⫺47.8 to 161.8 7.5 to 162.4 ⫺40 to 57 30 to 191 12 to 202 34.8 to 202 2 to 185 6.6 to 80.7 25.4 to 161 ⫺31 to 155.7 ⫺103.5 to 83 ⫺18 to 134 14.8 to 151.1 ⫺94 to 50 ⫺19 to 140 ⫺51 to 130.6 ⫺135.1 to 44.2 ⫺43 to 195.8 ⫺30.4 to 187.3 ⫺38 to ⬎101 ⫺68 to 194 ⫺29.7 to 174.1 6.9 to 232 ⫺66 to 170.6 ⫺26 to 300 2 to 298 87.3 to 220 ⫺20 to 198 10 to 131.7 ⫺55.5 to 142 ⫺110.5 to 47 ⫺62 to 159.6 ⫺10 to 345 ⫺95 to 140 ⬍ ⫺80 to 281 ⫺35 to 340 9 to 194 ⫺17 to 180.4 ⫺24.8 to 173.1 53 to 174.1 ⫺38 to 163 ⫺97 to 57.3 ⫺35.7 to 83.5 ⫺122.6 to 31.6 ⫺80.1 to 60 ⫺49.8 to 48.7 up to 178.5

Viscosity, mN · s · m⫺2 0.401(0), 0.335(15), 0.299(30) 0.347(15) 1.267(25), 0.883(50), 0.662(75) 0.964(25), 0.710(50), 0.547(75) 0.837(25), 0.621(50), 0.483(75) 3.035(50), 1.562(75), 0.961(100) 12.9(25), 4.417(50), 2.093(75) 5.607(45) 0.980(20), 0.912(25), 0.650(50) 57.5(25), 41.07(30), 12.3(50) 2.453(15), 1.803(30), 1.321(50) 0.882(0), 0.625(25), 0.467(50) 1.079(25), 0.692(50), 0.485(75) 0.555(0), 0.413(25), 0.321(50) 0.439(20)

3.042(25), 1.875(50), 1.271(75) 1.948(25), 1.289(50), 0.917(75) 1.28(20) 1.277(0), 0.838(25), 0.598(50) 10.9(25), 4.590(50) 0.805(20) 3.711(25)

1.721(20), 1.286(40), 0.648(100) 1.5(25) 0.72(25) 0.918(25), 0.619(50), 0.449(75) 9.03(25) 0.637(25), 0.466(50), 0.356(75) 5.62(20), 4.76(25) 19.91(20), 11.17(35), 7.85(45) 3.23(50), 1.92(75) 1.324(25), 0.962(50), 0.739(75) 1.044(25), 0.783(50), 0.628(75) 0.839(55), 0.668(79) 0.505(15), 0.464(25), 0.362(50) 1.125(0), 0.779(25), 0.576(50) 0.442(0), 0.358(20) 0.785(⫺25), 0.575(0), 0.444(25) 0.522(⫺25), 0.398(0), 0.317(25) 2.41(20), 2.065(25)

short standard long

DEAN #37261

LEFT

(McGHP)

5.94

INTERACTIVE

top of rh base of rh

SECTION 5

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

cap height base of text

Surface tension, mN · m⫺1 Substance Dichloromethane 2,4-Dichlorophenol 1,2-Dichloropropane 1,3-Dichloropropane 2,2-Dichloropropane ␣,␣-Dichlorotoluene Diethanolamine 1,1-Diethoxyethane 1,2-Diethoxyethane Dimethoxymethane Diethylamine N,N-Diethylaniline Diethyl carbonate Diethyl decanedioate Diethyl ether Diethyl ethyl phosphonate Di(2-ethylhexyl) o-phthalate Diethyl maleate Diethyl 1,3-propanedioate (malonate) Diethyl oxalate Diethyl o-phthalate Diethyl succinate Diethyl sulfate Diethyl sulfide 1,2-Dihydroxybenzene 1,3-Dihydroxybenzene Diiodomethane Diisobutylamine Diisopentyl ether Diisopropylamine Diisopropyl ether 1,2-Dimethoxybenzene 1,1-Dimethoxyethane 1,2-Dimethoxyethane Dimethoxymethane N,N-Dimethylacetamide Dimethylamine N,N-Dimethylaniline 2,4-Dimethylaniline 2,2-Dimethylbutane 2,3-Dimethylbutane 2,3-Dimethyl-1-butanol Dimethyl carbonate 1,1-Dimethylcyclopentane Dimethyl ether N,N-Dimethylformamide 2,4-Dimethylheptane 2,5-Dimethylheptane

a

b

Liquid range, ⬚C

30.41 46.59 31.42 36.40 23.60(20) 41.26

0.1284 0.1221 0.1240 0.1233 22.53(30) 0.1035

368(30), 109.5(50), 28.7(75)

23.46

0.1030

23.87 22.71 36.59 28.62 34.68 18.92 30.63

0.1291 0.1143 0.1040 0.1100 0.0959 0.0908 0.0975

⫺95 to 40 42 to 210 ⫺100 to 96 ⫺99.5 to 122 ⫺35 to 69 ⫺16 to 205 28 to 269 ⫺100 to 102.2 ⫺74 to 121.4 up to 88 ⫺50 to 55.5 ⫺38 to 217 ⫺43 to 126

34.67 33.91

0.1039 0.1042

⫺116 to 34.6 up to 198 ⫺50 to 384 ⫺8.8 to 225.3 ⫺49.9 to 199.3

0.283(0), 0.224(25) 1.627(15), 0.969(45), 0.743(65) 33.67(35), 21.40(45) 3.57(20), 3.14(25) 2.15(20), 1.94(25)

34.32 38.47 33.97 35.47 27.33 47.6 54.8 70.21 24.00 24.76 21.03 19.89 34.4 23.90 48.0(25) 23.59 32.40(30) 29.50 38.14 39.34 18.29 19.38 26.22 31.94 23.78 14.97 36.76(20) 23.21 23.21

0.1119 0.0963 0.1041 0.0976 0.1106 0.0849 0.0717 0.1613 0.0912 0.0871 0.1077 0.1048 0.0642 0.1159 0.1199 29.50(50) 0.1265 0.1049 0.0996 0.0990 0.1000 0.0992 0.1343 0.1016 0.1478 34.40(40) 0.0929 0.0929

⫺40.6 to 185.4 ⫺40 to 295 ⫺21 to 217.7 ⫺25 to 208 ⫺104 to 92.1 104 to 245.5 110 to 276 6 to 181 ⫺77 to 139 up to 172.5 ⫺61 to 83.5 ⫺87 to 68 22.5 to 206 ⫺113 to 64.5 ⫺68 to 85 ⫺104.8 to 42 ⫺20 to 165.5 ⫺92 to 6.9 2.5 to 194 ⫺14 to 214 ⫺100 to 49.7 ⫺128 to 58 ⫺14 to 118 0.5 to 91 ⫺70 to 87.5 ⫺141 to ⫺24.9 ⫺60 to 153 ⬍ ⫺100 to 133 ⬍ ⫺100 to 136

Viscosity, mN · s · m⫺2 0.533(0), 0.449(15), 0.393(30) 0.865(20), 0.700(25) 0.769(15), 0.619(30)

0.65(20)

3.838(0), 1.15(50), 0.750(75) 0.868(15), 0.748(25)

2.311(15), 1.618(30) 9.18(35), 6.41(45)

0.558(0), 0.422(25)

1.40(11), 1.012(20) 0.393(25), 0.300(50), 0.237(75) 0.379(25) 3.281(25), 2.184(40) 0.670(⫺10), 0.530(10), 0.455(25) 0.340(15), 0.325(20) 1.956(25), 1.279(50), 0.896(75) 0.300(⫺25), 0.232(0) 1.300(25), 0.911(50), 0.675(75) 0.351(25), 0.330(30) 0.361(25), 0.342(30)

1.176(0), 0.794(25), 0.624(50)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.95

PHYSICAL PROPERTIES

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

top of rh base of rh cap height base of text

Surface tension, mN · m⫺1 Substance 2,6-Dimethylheptane Dimethyl hexanedioate Dimethyl maleate Dimethyl malonate 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane 2,4-Dimethylphenol 2,5-Dimethylphenol 3,4-Dimethylphenol 3,5-Dimethylphenol Dimethyl o-phthalate 2,2-Dimethylpropane Dimethyl succinate Dimethyl sulfate Dimethyl sulfide Dimethyl sulfite Dimethyl sulfoxide 1,4-Dioxane Dipentyl ether Dipentyl o-phthalate Dipentyl sulfide Dipentylamine Diphenyl ether 1,2-Dipropoxyethane Dipropoxymethane Dipropylamine Dipropyl carbonate Dipropylene glycol butyl ether Dipropylene glycol ethyl ether Dipropylene glycol isopropyl ether Dipropylene glycol methyl ether Dipropyl ether Dodecane 1-Dodecanol Epichlorohydrin 1,2-Epoxybutane 1,2-Ethanediamine 1,2-Ethanediol Ethanesulfonic acid Ethanesulfonyl chloride Ethanethiol Ethanol Ethanolamine Ethoxybenzene (phenetol) 2-Ethoxyethanol Ethyl acetate

a

b

22.17 38.26 40.73 39.72 19.94 21.96 20.09 21.59 34.57 36.72 35.75 34.09

0.0887 0.1138 0.1220 0.1208 0.0957 0.0995 0.0972 0.0996 0.0869 0.0850 0.0910 0.0807

12.05(20) 39.00 41.26 26.07 36.48 43.54(20) 36.23 26.66 32.56 29.55 45.36 28.70 25.03 25.17 24.86 28.94 28.2(25) 27.7(25) 25.9(25)

10.98(30) 0.1191 0.1163 0.0805 0.1253 42.41(30) 0.1391 0.0925 0.0739 0.0876 0.1017 0.0780 0.0972 0.0953 0.1022 0.1015

⫺103 to 135 8 to ⬎112 ⫺19 to 202 ⫺62 to 181 ⫺124 to 79 up to 90 ⫺120 to 80.4 ⫺135 to 86 24.5 to 211 74.5 to 211.5 61 to 227 64 to 222 5.5 to 284 ⫺16.6 to 9.5 19 to 196.4 ⫺31.8 to 188 ⫺98 to 37 up to 127 18.5 to 189 11.8 to 101.2 ⫺69 to 190

0.1047 0.0884 0.0748 0.1360 0.1398 0.0890 0.0824 0.1177 0.0793 0.0832 0.1117 0.1104 0.0897 0.1161

Viscosity, mN · s · m⫺2

14(20) 3.54(20), 3.21(25)

0.406(20) 0.361(20)

1.55(80) 3.00(80) 2.42(80) 14.4(25), 5.309(50), 2.824(75) 0.328(0), 0.303(5)

0.356(0), 0.289(20), 0.265(36) 0.715(30), 0.436(80) 2.47(20), 1.192(55), 0.849(80) 1.439(15), 1.087(30), 0.787(50) 1.188(15), 0.922(30) 17.03(35), 11.51(45)

53 to 302 27 to 258

4.66 (55), 1.04(130) 2.130(50), 1.407(75), 1.023(100)

⫺63 to 109 up to 168 up to ⬎103

0.517(25), 0.377(50), 0.288(75)

up to 80

28.8(25) 22.60 27.12 31.25 39.76 23.9(20) 44.77 50.21 45.74 43.43 25.06 24.05 51.11 35.17 30.59 26.29

Liquid range, ⬚C

4.23(25) 3.11(25) 386(25)

⫺117 to 188

3.1(25)

⫺126 to 89.6 ⫺10 to 216 24 to 259 ⫺26 to 117 ⫺150 to 63 11 to 117.3 ⫺12.6 to 197.3 ⫺17 to ⬎123 up to 177 ⫺148 to 35 ⫺114 to 78 10.5 to 171 ⫺29.5 to 170 ⫺70 to 135 ⫺84 to 77

0.542(0), 0.396(25), 0.304(50) 2.277(0), 1.378(25), 0.930(50) 1.20(25) 0.419(15), 0.358(30) 1.54(20), 1.226(30) 26.09(15), 13.55(30)

0.364(0), 0.287(25) 1.786(0), 1.074(25), 0.694(50) 21.1(25), 8.560(50), 3.935(75) 1.364(15), 1.197(25), 0.817(50) 2.04(20), 1.85(25) 0.578(0), 0.423(25), 0.325(50)

short standard long

DEAN #37261

LEFT

(McGHP)

5.96

INTERACTIVE

top of rh base of rh

SECTION 5

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

cap height base of text

Surface tension, mN · m⫺1 Substance Ethyl acetoacetate Ethylamine N-Ethylaniline Ethylbenzene Ethyl benzoate Ethyl butanoate 2-Ethylbutanoic acid 2-Ethyl-1-butanol Ethyl carbamate Ethyl chloroacetate Ethyl chloroformate Ethyl trans-cinnamate Ethyl crotonate Ethyl cyanoacetate Ethylcyclohexane Ethyl dichloroacetate Ethyl dodecanoate Ethylene carbonate Ethylenediamine Ethylene glycol Ethyleneimine Ethylene oxide Ethyl formate Ethyl fumarate Ethylhexadecanoate Ethyl hexanoate 2-Ethyl-1-hexanol Ethyl isobutanoate Ethyl isothiocyanate Ethyl lactate Ethyl 3-methylbutanoate Ethyl methyl ether Ethyl methyl sulfide Ethyl nitrate 3-Ethylpentane Ethyl pentanoate Ethyl propanoate Ethyl propyl ether Ethyl salicylate Ethyl thiocyanate o-Ethyltoluene p-Ethyltoluene Ethyl trichloroacetate Fluorobenzene 1-Fluorohexane 1-Fluoropentane o-Fluorotoluene m-Fluorotoluene p-Fluorotoluene

a

b

34.42 22.63 39.00 31.48 37.16 26.55 26.3(20) 25.06(15)

0.1015 0.1372 0.1070 0.1094 0.1059 0.1045 24.32(25)

34.18 28.90 39.99 29.31 38.80 27.78 34.89 30.05

0.1177 0.1084 0.1045 0.1066 0.1092 0.1054 0.1158 0.0863

44.77 50.21 7.9(20) 27.66 26.47 33.90 32.86 27.73 30.0(22) 25.33 38.69 30.72 25.79 18.56 27.63 30.81 22.52 27.15 26.72 21.92 31.00 37.28 32.33 30.98 32.97 29.67 23.41 22.81

0.1398 0.0890

0.1046 0.1326 0.0983 0.1006 0.1317 0.1286 0.1345 0.1032 0.0999 0.1168 0.1054 0.1091 0.1226 0.1060 0.1075 0.1073 0.1204 0.1001 0.1315

32.31 30.44

0.1257 0.1109

0.1664 0.1315 0.1056 0.0859 0.0960

Liquid range, ⬚C ⫺45 to 181 ⫺81 to 16.6 ⫺63.5 to 203 ⫺95 to 136 ⫺35 to 212 ⫺98 to 121 ⫺14 to 194 ⬍ ⫺15 to 146 50 to 184 ⫺21 to 144 ⫺81 to 93 10 to 271 up to 138 ⫺22 to 206 ⫺111 to 132 up to 155 ⫺10 to 271 36 to 248 11 to 117 up to 198 ⫺78 to 56 ⫺111 to 10.6 ⫺80 to 54 68 to ⬎148 22 to ⬎191 up to 168 ⫺70 to 185 ⫺88 to 110 ⫺6 to 132 ⫺26 to 155 ⫺99 to 135 ⫺113 to 7.4 ⫺106 to 67 ⫺95 to 88 ⫺119 to 93.5 ⫺91 to 145 ⫺74 to 99 ⫺79 to 63 2 to 234 up to 145 ⫺81 to 165 ⫺62 to 162 up to 168 ⫺42 to 85 ⫺103 to 93 ⫺120 to 63 ⫺62 to 115 ⫺87 to 115 ⫺56 to 117

Viscosity, mN · s · m⫺2 1.419(20), 1.508(25) 2.047(25), 1.231(50), 0.825(75) 1360.631(25), 0.482(50), 0.380(75) 2.407(15), 1.751(30) 0.771(15), 0.613(25) 3.3(20) 8.021(15), 5.892(25) 0.916(105), 0.715(120)

8.7(20) 3.256(15), 2.148(30) 1.139(0), 0.784(25), 0.579(50)

1.85(40) 1.540(18) 26.09(15), 13.35(30), 6.554(50) 0.418(25) 0.3(0) 0.419(15), 0.358(30), 0.300(50)

6.271(25), 2.631(50), 1.360(75)

2.44(25)

0.373(20), 0.354(25)

0.847(20) 0.564(15), 0.473(30), 0.380(50) 0.401(0), 0.323(20), 0.225(60) 1.772(45)

0.620(15), 0.517(30), 0.423(50)

0.680(20), 0.601(30) 0.608(20), 0.534(30) 0.622(20), 0.522(30)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.97

PHYSICAL PROPERTIES

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

top of rh base of rh cap height base of text

Surface tension, mN · m⫺1 Substance Formamide Formanilide Formic acid Furan 2-Furancarboxaldehyde 2-Furanmethanol Glycerol Glycerol tris(acetate) Glycerol tris(nitrate) Glycerol tris(oleate) Glycerol tris(palmitate) Glycerol tris(sterate) Heptanal Heptane Heptanoic acid 1-Heptanol 2-Heptanol 3-Heptanol 4-Heptanol 2-Heptanone 4-Heptanone 1-Heptene Heptylamine Hexadecane 1,5-Hexadiene Hexafluorobenzene Hexamethyldisiloxane Hexamethylphosphoramide Hexane Hexanenitrile Hexanoic acid 1-Hexanol 2-Hexanone 1-Hexene Hexyl acetate 4-Hydroxy-4-methyl-2pentanone Iodobenzene 1-Iodobutane 2-Iodobutane Iodoethane 1-Iodoheptane 1-Iodohexadecane 1-Iodohexane Iodomethane 1-Iodo-2-methylpropane 1-Iodooctane 1-Iodopentane 1-Iodopropane

a

b

Liquid range, ⬚C

59.13 44.30 39.87 24.10(20) 46.41 ca. 38(20) 63.14(17) 37.88 55.74 36.03 32.26 32.73 28.64 22.10 29.88

0.0842 0.0875 0.1098 23.38(25) 0.1327

2.6 to 220 47 to 271 8 to 101 ⫺86 to 31 ⫺36.5 to 162 ⫺31 to 171

28.76 28.11 22.28 25.96 29.18 20.93 22.6(20) 17.01 33.8(20) 20.44 29.64 28.05(20) 27.81 28.18 20.47 28.44 31.0(20)

0.1056 0.1060 0.0991 0.0783 0.0854 0.1028

41.52 30.82 30.32 31.67 32.18 34.49 31.63 33.42 30.26 32.51 31.41 31.64

62.5(25) 0.081 0.2504 0.0699 0.0672 0.0685 0.0920 0.0980 0.0848

0.0763 0.1022 0.0907 27.55(25) 0.0801 0.1092 0.1027 0.0970

0.1123 0.1031 0.1056 0.1286 0.0887 0.0880 0.0845 0.1234 0.1072 0.0915 0.1014 0.1136

18 to 290 13 to ⬎160 ⫺5 to ⬎233 65 to 320 ⫺43 to 153 ⫺91 to 98 ⫺8 to 222 ⫺34 to 176 up to 159 ⫺70 to 157 ⫺35 to 151 ⫺32 to 143.7 ⫺120 to 93.6 ⫺23 to 156 18.2 to 286.8 ⫺140.7 to 59.5 5.1 to 80.3 ⫺67 to 101 7 to 232 ⫺95.4 to 68.7 ⫺80 to 163.6 ⫺3 to 205 ⫺44.6 to 157.5 ⫺55.5 to 127.6 ⫺140 to 63.5 ⫺81 to 171 ⫺44 to 168 ⫺31 to 188 ⫺103.5 to 131 ⫺104 to 120 ⫺111 to 72.4 ⫺48 to 204 23 to ⬎207 up to 180 ⫺66.5 to 42.5 ⫺93.5 to 121 ⫺46 to 226 ⫺85 to 155 ⫺101 to 102.6

Viscosity, mN · s · m⫺2 4.320(15), 2.296(30), 1.833(50) 1.65(120) 1.966(15), 1.607(25), 1.030(50) 0.380(20), 0.361(25) 2.501(0), 1.587(25), 1.143(50) 4.62(25) 934(25), 152(50), 39.8(75) 36.0(20), 13.6(40)

0.977(15) 0.523(0), 0.416(20), 0.341(40) 3.84(25), 2.282(50), 1.488(75) 8.53(15), 5.810(25), 2.603(50) 3.955(25), 1.799(50), 0.987(75) 1.957(50), 0.976(75), 0.584(100) 4.207(25), 1.695(50), 0.882(75) 0.854(15), 0.686(30), 0.407(50) 0.736(20) 0.441(0), 0.340(25), 0.273(50) 1.314(25), 0.865(50), 0.600(75) 3.032(25), 1.879(50), 1.260(75) 0.275(20), 0.244(36) 2.789(25), 1.730(50), 1.151(75) 3.47(20) 0.405(0), 0.313(20), 0.271(40) 1.041(15), 0.830(30), 0.650(50) 3.525(15), 2.511(30) 6.203(15), 3.872(30), 2.271(50) 0.584(25), 0.429(50), 0.329(75) 0.326(0), 0.252(25), 0.202(50) 6.621(0), 2.798(25), 1.829(50) 1.554(25), 1.117(50), 0.854(75)

0.617(15), 0.540(30), 0.444(50)

0.594(0), 0.500(20), 0.424(40) 0.875(20), 0.697(40)

0.837(15), 0.670(30), 0.541(50)

short standard long

DEAN #37261

LEFT

(McGHP)

5.98

INTERACTIVE

top of rh base of rh

SECTION 5

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

cap height base of text

Surface tension, mN · m⫺1 Substance 2-Iodopropane p-Iodotoluene ␣-Ionone ␤-Ionone Isobutanenitrile Isobutyl acetate Isobutylamine Isobutylbenzene Isobutyl formate Isobutyl propanoate Isopentyl acetate Isophorone Isopropyl acetate Isopropylamine Isopropylbenzene Isopropyl formate Lactonitrile D-Limonene (⫾)-Mandelonitrile Methacrylic acid Methacrylonitrile Methanesulfonic acid Methanethiol Methanol o-Methoxybenzaldehyde p-Methoxybenzaldehyde Methoxybenzene 2-Methoxyethanol 2-(2-Methoxyethoxy)ethanol 1-Methoxy-2-nitrobenzene o-Methoxyphenol p-Methoxytoluene N-Methylacetamide Methyl acetate Methyl acetoacetate Methyl acrylate Methylamine N-Methylaniline o-Methylaniline m-Methylaniline Methyl benzoate 2-Methyl-1,2-butadiene 2-Methylbutane Methyl butanoate 3-Methylbutanoic acid 2-Methyl-1-butanol 2-Methyl-2-butanol 3-Methyl-1-butanol 3-Methyl-2-butanol

a

b

Liquid range, ⬚C

29.35 39.23 34.10 35.36 24.93(20) 25.59 24.48 29.39 26.14 30.92 26.75

0.1107 0.0965 0.0949 0.0950 23.84(30) 0.1013 0.1092 0.0961 0.1122 0.1270 0.0989

24.44 19.91 30.32 24.56 38.31 29.50 45.90 26.5(25) 24.4(20) 52.28 28.09 24.00 45.34 44.69 38.11 33.30 34.8(25) 48.62 41.2 36.20 33.67(30) 27.95 34.98

0.1072 0.0972 0.1054 0.1147 0.0960 0.0929 0.0988

⫺90 to 89.5 up to 211 ⬎124 ⬎128 ⫺71.5 to 104 ⫺99 to 116.5 ⫺86.6 to 68 ⫺51.5 to 172.8 ⫺95.5 to 98.4 ⫺71 to 137 ⫺78.5 to 142 ⫺8.1 to 215.2 ⫺73 to 89 ⫺95 to 31.7 ⫺96 to 154

0.0893 0.1696 0.0773 0.1105 0.1047 0.1204 0.0984 29.9(75) 0.1185 0.0943 0.1071 30.62(50) 0.1289 0.0944

22.87 39.32

0.1488 0.0970

⫺40 to ⬎103 ⫺96.5 to 178 ⫺10 to 170 16 to 163 ⫺35.8 to 90.3 20 to ⬎167 ⫺123 to 6.0 ⫺97.7 to 64.7 37 to 238 ⫺1 to 248 ⫺37.5 to 153.8 ⫺85.1 to 124 ⫺50 to 194 10.5 to 277 28 to 205 up to 174 30.6 to 206 ⫺98 to 57 27.5 to 171.7 ⫺76.5 to 80.2 ⫺93.5 to ⫺6.3 ⫺57 to 196

40.10

0.1171

⫺15 to 199.5

17.20 27.48 27.28 21.5(25) 24.18 25.76 23.0(25)

0.1103 0.1145 0.0886

up to 30 ⫺85.8 to 103 ⫺29.3 to 176.5 ⬍ ⫺70 to 128 ⫺9.0 to 102.0 ⫺117 to 131 up to 112.9

0.0748 0.0820

Viscosity, mN · s · m⫺2 0.732(15), 0.620(30), 0.506(50)

0.551(15), 0.456(30) 0.676(25), 0.493(50), 0.370(75) 0.770(0), 0.571(25), 0.367(50) 0.680(20) 0.872(20), 0.790(25) 4.201(0), 2.329(25), 1.415(50) 0.559(20) 0.454(0), 0.325(25) 1.075(0), 0.737(25), 0.547(50) 0.512(20) 2.01(30)

1.32(20) 0.392(20)

0.793(0), 0.676(10), 0.544(25)

1.152(15), 1.056(25), 0.747(50) 1.71(20), 1.60(25) 3.48(25), 1.61(60)

3.88(30), 2.54(45) 0.477(0), 0.364(25), 0.284(50) 1.398(20) 0.319(⫺25) 2.042(25), 1.222(50), 0.825(75) 3.823(25), 1.936(50), 1.198(75) 3.306(25), 1.679(50), 1.014(75) 2.298(15), 0.206(20), 1.673(30) 0.266(0.3), 0.233(20) 0.376(⫺25), 0.277(0), 0.214(25) 0.580(20), 0.459(40), 0.406(50) 2.731(15), 2.411(20) 5.50(20), 4.453(25), 1.963(50) 5.48(15), 2.81(30) 4.81(15), 2.96(30), 1.842(50) 3.51(25)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.99

PHYSICAL PROPERTIES

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

top of rh base of rh cap height base of text

Surface tension, mN · m⫺1 Substance

a

b

Liquid range, ⬚C ⫺137.6 to 31 ⫺133.8 to 38.6 ⫺168 to 20 ⫺99 to 117 ⫺101 to 129 ⫺32 to 130 ⫺22.5 to 201 ⫺126.6 to 100.9 7 to 165

2-Methyl-1-butene 2-Methyl-2-butene 3-Methyl-1-butene 2-Methylbutyl acetate 3-Methylbutyronitrile Methyl chloroacetate Methyl cyanoacetate Methylcyclohexane cis-2-Methylcyclohexanol

18.81 19.70 16.42 26.75 27.58 37.90 41.32 26.11 32.45

0.1148 0.1271 0.1031 0.0989 0.0827 0.1304 0.1074 0.1130 0.0770 (mixed isomers)

trans-2-Methylcyclohexanol cis-3-Methylcyclohexanol

29.08

0.0629 (mixed isomers)

trans-3-Methylcyclohexanol cis-4-Methylcyclohexanol

28.80(30) 29.07

2-Methylcyclohexanone 3-Methylcyclohexanone 4-Methylcyclohexanone Methylcyclopentane Methyl decanoate Methyl dichloroacetate Methyl dodecanoate N-Methylformamide Methyl formate Methyl heptanoate 4-Methyl-3-heptanol 5-Methyl-3-heptanol Methyl hexadecanoate (palmitate) 2-Methylhexane 3-Methylhexane Methyl hexanoate Methyl isobutanoate 1-Methyl-4-isopropylbenzene ( p-cymene) Methyl methacrylate

34.06 33.06 32.83 24.63 30.33 37.00 31.37 37.96(30) 28.29 28.95

1-Methylnaphthalene Methyl octadecanoate 2-Methyloctane 4-Methyloctane Methyl octanoate Methyl oleate 2-Methylpentane 3-Methylpentane

0.0690 (mixed isomers) 0.1027 0.0925 0.0935 0.1163 0.0912 0.1219 0.0893 35.02(50) 0.1572 0.0987

31.50

0.0775

21.22 21.73 28.47 25.99 28.83

0.0966 0.0970 0.1045 0.1131 0.0877

2829(30) 39.96 32.20 23.76 24.22 29.93 31.3(25) 19.37 20.26

⫺2 to 167.5 ⫺6 to 168 ⫺0.5 to 167 ⫺9.2 to 173

up to 162 up to 169 up to 171 ⫺142.2 to 71.8 ⫺18 to 223 ⫺52 to 143 4.8 to 262 ⫺4 to 199.5 ⫺99 to 31.7 ⫺55.8 to 173.5 ⫺123 to 170 ⫺91 to 172 32 to ⬎196 ⫺118 to 90 ⫺119 to 92 ⫺71 to 151 ⫺84.7 to 92.5 ⫺48 to 100

0.0934 0.0775 0.0940 0.0940 0.1002 25.4(100) 0.0997 0.1060

⫺30.4 to 245 38 to ⬎215 ⫺80.3 to 143.2 ⫺113 to 142 ⫺40 to 192.9 ⫺19.9 to ⬎218 ⫺154 to 60.3 ⫺163 to 63

Viscosity, mN · s · m⫺2

0.872(20)

3.824(50), 3.398(55), 2.687(65) 0.679(25), 0.501(50), 0.390(75) 18.08(25), 13.60(30)

37.13(25), 25.14(30) 19.7(25), 17.23(30)

25.62(16), 15.60(30)

0.653(0), 0.478(25), 0.364(50)

1.678(25), 1.155(50), 0.824(75) 0.424(0), 0.360(15), 0.325(25) 1.085(25), 0.702(50), 0.497(75) 1.178(25), 0.762(50), 0.536(75)

0.378(20) 0.372(20), 0.350(25) 0.672(0), 0.523(20), 0.419(40) 3.402(20) 0.632(20)

4.88(20) 0.372(0), 0.286(25), 0.226(50) 0.395(0), 0.307(25), 0.292(30)

short standard long

DEAN #37261

LEFT

(McGHP)

5.100

INTERACTIVE

top of rh base of rh

SECTION 5

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

cap height base of text

Surface tension, mN · m⫺1 Substance 4-Methylpentanenitrile Methyl pentanoate 2-Methyl-1-pentanol 3-Methyl-1-pentanol 4-Methyl-1-pentanol 2-Methyl-2-pentanol 3-Methyl-2-pentanol 4-Methyl-2-pentanol 2-Methyl-3-pentanol 3-Methyl-3-pentanol 4-Methyl-2-pentanone Methyl phenyl sulfide N-Methyl propanamide 2-Methylpropanenitrile Methyl propanoate 2-Methylpropanoic acid 2-Methyl-1-propanol 2-Methyl-2-propanol 2-Methylpropene 1-Methylpropyl acetate 2-Methyl-1-propylamine 2-Methylpropyl formate 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine N-Methyl-2-pyrrolidinone Methyl salicylate Methyl tetradecanoate 2-Methyltetrahydrofuran Methyl thiocyanate Morpholine Naphthalene p-Nitroaniline Nitrobenzene Nitroethane Nitromethane 1-Nitro-2-methoxybenzene o-Nitrophenol 1-Nitropropane 2-Nitropropane o-Nitrotoluene m-Nitrotoluene p-Nitrotoluene Nonane Nonanoic acid 1-Nonanol 5-Nonanone 1-Nonene Octadecane

a

b

28.89 27.85 26.98 26.92 25.93 25.07 27.14 24.67 26.43 25.48 23.64(20) 42.81 31.29(20)

0.0917 0.1044 0.0819 0.0789 0.0743 0.0861 0.0919 0.0821 0.0914 0.0888 19.62(60) 0.1238 29.12(50)

27.58 25.55(20) 24.53 20.02(15) 14.84 25.72 24.48 26.14 36.11 37.35 37.71

0.1258 25.13(25) 0.0795 19.10(30) 0.1319 0.1054 0.1092 0.1122 0.1243 0.1153 0.1141

42.15 31.00

0.1174 0.0800

40.66 37.63(20)

0.1305 36.24(30)

60.62 48.62 35.27 40.72 48.62 47.35 32.62 32.18 44.10 43.54 42.26 24.72

0.0923 0.1185 0.1255 0.1678 0.1185 0.1174 0.1009 0.1158 0.1174 0.1118 0.0974 0.0935

29.79 28.72 24.90 29.98

0.0789 0.0975 0.0938 0.0843

Liquid range, ⬚C ⫺51.1 to 156.5 up to 128 up to 148 up to 153 up to 152 ⫺103 to 121 up to 134 ⫺90 to 122 up to 126 ⫺23.6 to 123 ⫺84 to 116.5 ⫺15 to 188 ⫺43 to ⬎146 ⫺72 to 108 ⫺88 to 80 ⫺47 to 154 ⫺108 to 108 25.8 to 82.4 ⫺140 to ⫺6.9 ⫺87 to 68 ⫺96 to 98 ⫺66.7 to 129 ⫺18.3 to 144 3.8 to 145 ⫺24.4 to 202 ⫺8 to 223 18.4 to 323 ⬍ ⫺75 to 78 ⫺5 to 133 ⫺4.9 to 128 80 to 217.7 147 to 332 5.8 to 210.8 ⫺90 to 114 ⫺28.4 to 101.2 95 to 273 45 to 216 ⫺108 to 131.1 ⫺91.3 to 120.3 ⫺10 to 222 15.5 to 231.9 52 to 238 ⫺53.5 to 150.8 12.5 to 254.5 ⫺5.5 to 215 ⫺50 to 187 ⫺81 to 146 28.1 to 316.3

Viscosity, mN · s · m⫺2 0.980(20), 0.843(30) 0.713(20)

4.074(25)

0.585(20), 0.522(30), 0.406(50) 6.06(20), 4.58(30), 3.56(40) 0.551(15), 0.456(30) 0.581(0), 0.431(25), 0.333(50) 1.857(0), 1.226(25), 0.863(50) 4.70(15), 2.876(30) 1.421(50), 0.678(75)

21.7(25) 0.680(20) 0.805(20), 0.710(30)

1.666(25) 1.102(75), 0.815(100) 0.777(⫺20), 0.601(0), 0.536(10) 64.3(0) 2.53(15), 1.79(30), 1.247(50) 0.967(80), 0.780(100) 2.165(15), 1.863(25), 1.262(50) 0.940(0), 0.688(25), 0.526(50) 0.692(15), 0.596(30), 0.481(50) 2.343(45) 0.798(25), 0.589(50), 0.460(75) 0.750(25) 2.37(20), 1.63(40) 0.233(20), 1.60(40) 1.20(60) 0.964(0), 0.666(25), 0.488(50) 7.011(25), 3.712(50), 2.234(75) 14.3(20), 9.123(25), 4.032(50) 1.199(25), 0.834(50), 0.619(75) 0.620(20), 0.586(25) 2.487(50), 1.609(75), 1.132(100)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

5.101

PHYSICAL PROPERTIES

TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

top of rh base of rh cap height base of text

Surface tension, mN · m⫺1 Substance

a

b

Liquid range, ⬚C

Octamethylcyclotetrasiloxane Octane Octanenitrile Octanoic acid 1-Octanol 2-Octanol 1-Octene Oleic acid 4-Oxopentanoic acid Paraldehyde Parathion Pentachloroethane Pentadecane Pentanal Pentane 1,5-Pentanediol 2,4-Pentanedione Pentanenitrile Pentanoic acid 1-Pentanol 2-Pentanol 3-Pentanol 2-Pentanone 3-Pentanone 1-Pentene cis-2-Pentene trans-2-Pentene Pentyl acetate Pentylamine Phenol 2-Phenylacetamide Phenyl acetate Phenylacetonitrile 1-Phenylethanol Phenylhydrazine Phenyl isothiocyanate Phenyl salicylate (⫾)-␣-Pinene L-␤-Pinene Piperidine 1,2-Propanediol (see propylene glycol) 1,3-Propanediol Propanenitrile (propionitrile) 1-Propanethiol 2-Propanethiol Propanoic acid Propanoic anhydride 1-Propanol

20.19 23.52 29.61 29.21(20) 29.09 27.96 23.68 32.80(20) 41.69 28.28 39.2(25) 37.09 28.78 27.96 18.25 43.2(20) 33.28 27.44(20) 28.90 27.54 25.96 24.60(20) 24.89 27.36 18.20 19.71 18.90 27.66 24.4(13) 43.54 46.26

0.0811 0.0951 0.0802 28.7(25) 0.0795 0.0820 0.0958 27.94(90) 0.0763 0.1062

2.20(20) 0.546(20), 0.433(40), 0.355(60) 1.811(15), 1.356(30) 5.020(25), 2.656(50), 1.654(75) 10.64(15), 6.125(30), 3.232(50)

44.57 42.88 48.14 42.73 45.20 28.35 28.26 31.79

0.1155 0.1038 0.1292 0.1086 0.0976 0.0944 0.0934 0.1153

17 to 176 ⫺56.8 to 125.7 ⫺45.6 to 205 16.6 to 239 ⫺15.5 to 195 ⫺31.6 to 180 ⫺102 to 121 13.4 to 360 33 to 246 12.6 to 124 6 to 375 ⫺29.9 to 160 9.9 to 270 ⫺92 to 103 ⫺129.7 to 36.0 ⫺18 to 239 ⫺23.1 to 138 ⫺92 to 141.3 ⫺33.7 to 186 ⫺79 to 137.5 ⫺73 to 119.3 ⫺69 to 116 ⫺76.8 to 102 ⫺39.0 to 102 ⫺165 to 30.1 ⫺151 to 37.0 ⫺140 to 36.3 ⫺70.8 to 149.2 ⫺55 to 104 41 to 182 157 to bp ⬍45 to 196 ⫺23.8 to 233.5 20 to 204 19.5 to 243 ⫺30 to 163 44 to ⬎173 ⫺64 to 156 ⫺61 to 166 ⫺11 to 106

47.43 29.63 27.38 24.26 28.68 30.30(20) 25.26

0.0903 0.1153 0.1272 0.1174 0.0993 29.70(25) 0.0777

⫺27 to 214 ⫺92.8 to 97.2 ⫺113 to 68 ⫺131 to 52.6 ⫺20.5 to 141.1 ⫺45 to 170 ⫺127 to 97.2

56.0(20), 18.0(40) 0.294(25), 0.240(50), 0.202(75) 0.503(0), 0.385(25) 0.477(0), 0.357(25), 0.280(50) 1.030(25), 0.749(50), 0.569(75) 1.144(20), 1.061(25) 2.522(15), 1.722(30), 1.107(50)

0.1178 0.0857 0.1010 0.1121 0.1144 26.33(30) 0.0887 0.0874 0.1004 23.76(30) 0.0655 0.1047 0.1099 0.1172 0.0997 0.0994 0.1069 0.0788

Viscosity, mN · s · m⫺2

0.470(20), 0.447(25) 38.80(20), 27.64(25) 1.079(25), 0.692(50), 0.485(75) 15.30(25) 2.741(15), 2.070(30), 1.491(50) 2.814(22) 0.351(⫺25), 0.274(0), 0.224(25) 128(20) 0.6(20) 0.779(15), 0.637(30) 2.359(15), 1.774(30), 0.979(70) 4.650(15), 3.619(25), 1.820(50) 5.130(15), 2.780(30), 1.447(50) 7.337(15), 3.306(30), 1.473(50) 0.641(0), 0.473(25), 0.362(50) 0.592(0), 0.444(25), 0.345(50) 0.313(⫺25), 0.241(0), 0.195(25)

0.924(20), 0.862(25) 1.030(0), 0.702(25), 0.493(50) 3.437(50), 1.784(75), 1.099(100) 1.799(45) 1.93(25) 13.0(25), 4.553(50), 1.850(75)

1.61(25) 1.70(20), 1.41(25) 1.573(25), 0.958(50), 0.649(75)

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TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

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Surface tension, mN · m⫺1 Substance 2-Propanol 2-Propen-1-ol (allyl alcohol) Propionaldehyde (propanal) Propionamide Propyl acetate Propylamine Propylbenzene Propyl benzoate Propyl butanoate 1,2-Propylene glycol Propyleneimine 1,2-Propylene oxide Propyl formate Propyl isobutanoate Propyl nitrate Propyl pentanoate Propyl propanoate Propyne 2-Propyn-1-ol Pyridazine Pyridine Pyrimidine Pyrrole Pyrrolidine 2-Pyrrolidone Quinoline Salicylaldehyde Squalane Squalene Stearic acid Styrene Succinonitrile 1,1,2,2-Tetrabromoethane 1,1,2,2-Tetrachlorodifluoroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetradecane Tetradecanoic acid 1-Tetradecanol Tetraethylene glycol Tetraethyl lead Tetraethylsilane Tetraethyl silicate Tetrahydrofuran 2,5-Tetrahydrofurandimethanol Tetrahydro-2-furanmethanol 1,2,3,4-Tetrahydronaphthalene Tetrahydropyran

a

b

22.90 27.53

0.0789 0.0902

39.05 26.60 24.86 31.13 36.55 27.06

0.0909 0.1120 0.1243 0.1075 0.1069 0.1000

26.77 25.83 29.67 27.72 26.85 14.51 38.59 50.55 39.82 32.85 39.81 31.48

0.1119 0.1015 0.1237 0.0984 0.1059 0.1482 0.1270 0.1036 0.1306 0.1010 0.1100 0.0900

45.25 45.38

0.1063 0.1242

32.0(20) 53.26 52.37 26.13

30.98(30) 0.1079 0.1463 0.1133

38.75 32.86(15) 28.30 33.90 32.72 45(25) 30.50 25.22 23.63 26.5(25)

0.1268 31.27(30) 0.0869 0.0932 0.0703

39.96 35.55

0.1008 0.0954

0.0969 0.1079 0.0979

Liquid range, ⬚C ⫺89.5 to 82.4 ⫺129 to 98 ⫺81 to 48 79 to 222.2 ⫺93 to 101.6 ⫺83 to 42.2 ⫺99.2 to 159.2 ⫺51.6 to 98 ⫺95 to 143 ⫺60 to 188 up to 66 ⫺112 to 34 ⫺92.9 to 80.9 up to 135 ⫺100 to 110.1 ⫺75.9 to 122.5 ⫺76 to 122.5 ⫺102.8 to ⫺23.2 ⫺51.8 to 114 ⫺8 to 208 ⫺41.6 to 115.2 22 to 124 ⫺23.4 to 130 ⫺58 to 86.5 25 to 251 ⫺15 to 237 ⫺7 to 197 ⫺38 to 350 ⫺75 to ⬎285 67 to ⬎184 ⫺31 to 145 54.5 to 266 0 to 243.5 26.0 to 92.8 ⫺70.2 to 130.5 ⫺22 to 121 5.5 to 253.6 54 to ⬎250 39.5 to 289 ⫺6 to 328 ⫺136 to ⬎85 ⫺82 to 154.7 ⫺82.5 to 169 ⫺108.5 to 65 ⬍ ⫺50 to 265 ⬍ ⫺80 to 178 ⫺35.8 to 207.6 ⫺45 to 88

Viscosity, mN · s · m⫺2 2.859(15), 1.765(30), 1.028(50) 1.363(20), 0.914(40) 0.357(15), 0.321(25) 0.768(0), 0.544(25), 0.406(50) 0.376(25)

0.831(20) 40.4(0), 11.3(25), 4.770(50) 0.491(25) 0.327(20), 0.28(25) 0.669(0), 0.574(20), 0.417(40) 0.831(20) 1.053(20) 0.673(20) 1.68(20) 1.361(0), 0.879(25), 0.637(50) 2.085(0), 1.225(25), 0.828(50) 1.071(0), 0.704(25), 0.512(50) 13.3(25) 3.337(25), 1.892(50), 1.201(75) 2.90(20), 1.71(30), 1.669(45) 6.08(20) 12(25) 11.6(70) 1.050(0), 0.696(25), 0.507(50) 2.591(60), 2.008(75) 13.50(11), 9.797(20) 1.21(25), 1.208(30) 1.844(15), 1.456(30) 1.932(15), 0.798(30), 0.654(53) 2.128(25), 1.376(50), 0.953(75)

44.9(25)

0.605(0), 0.460(25), 0.359(50) 225(25) 6.24(20) 2.202(20), 2.003(25) 0.826(20), 0.764(25)

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TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

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Surface tension, mN · m⫺1 Substance

a

Tetrahydropyran-2-methanol Tetrahydrothiophene-1,1-dioxide (sulfolane) Tetrahydrothiophene oxide Thiacyclohexane Thiacyclopentane 2,2⬘-Thiodiethanol Thiophene Thymol Toluene p-Toluenesulfonyl chloride o-Toluidine m-Toluidine p-Toluidine m-Tolunitrile p-Tolunitrile Tribenzylamine Tribromomethane 1,2,3-Tribromopropane Tributylamine Tributyl borate Tributyl phosphite Tributyl phosphate Trichloroacetaldehyde Trichloroacetic acid 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane 2,4,6-Trichlorophenol 1,2,3-Trichloropropane Trichlorosilane ␣,␣,␣-Trichlorotoluene 1,1,2-Trichloro-1,2,2-trifluoroethane Tridecane 1-Tridecene Triethanolamine Triethylamine Triethylene glycol Triethyl phosphate Triethyl phosphite Trifluoroacetic acid 2,2,2-Trifluoroethanol Trimethylamine 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene 2,2,3-Trimethylbutane

34.1(25) 35.5(30)

b

Liquid range, ⬚C ⫺70 to 187 27.6 to 287.3

Viscosity, mN · s · m⫺2 11.0(20) 9.87(30), 6.280(50), 3.818(75) 52(30), 19(80)

36.06(20) 38.44 53.8(20) 34.00 33.95 30.90 42.41 42.87 40.33 39.58 38.85 39.79 42.41 48.14 47.99 26.47 26.2(20) 27.57 28.71 27.66 35.4 28.28 37.40 29.5(20) 18(25) 43.13 37.8(20) 20.43

33.74(40) 0.1342 0.1328 0.0821 0.1189 0.0903 0.1094 0.0979 0.0957 0.1013 0.1100 0.0953 0.1308 0.1267 0.0831 25.8(25) 0.0865 0.0666 0.1197 0.0895 0.1242 0.1351 28.8(25) 0.0955 37.05(25) 0.1076

17.75(20)

16.56(30)

27.73 28.01

0.0872 0.0884

22.70 47.33 31.81 25.73 15.64 20.6(33) 16.24 30.91 31.76 29.79 20.70

0.0992 0.0880 0.0928 0.0878 0.1844 0.1133 0.1040 0.1025 0.0897 0.0973

⫺10.2 to 282 ⫺39.4 to 84 49 to 232 ⫺94.9 to 110.6 67 to ⬎134 ⫺16.5 to 200 ⫺31 to 203 43.8 to 200 ⫺23 to 210 29.5 to 85 91-94 to bp 8.1 to 149.6 16.5 to 220 ⫺70 to 216 ⬍ ⫺70 to 234 up to ⬎125 ⫺79 to 289 ⫺57.5 to 97.8 57.5 to 196.5 ⫺30.4 to 74 ⫺37 to 114 ⫺84.8 to 87 ⫺111 to 23.8 69 to 246 ⫺14.7 to 157 ⫺127 to 32 ⫺5 to 223 ⫺35 to 47.7 ⫺5 to 235 ⫺13 to 232.8 20.5 to 335.4 ⫺114.7 to 88.8 ⫺7 to 285 ⫺56 to 215 up to 156 ⫺15.3 to 73 ⫺43.5 to 74 ⫺117 to 2.9 ⫺25.4 to 176.1 ⫺43.9 to 169 ⫺44.7 to 165 ⫺24.9 to 80.9

1.042(20), 0.971(25) 65.2(20) 0.871(0), 0.662(20), 0.353(82) 0.623(15), 0.523(30), 0.424(50) 5.195(15), 4.39(20) 4.418(15), 2.741(30) 1.945(45), 1.557(60)

2.152(15), 1.741(30), 1.367(50) 1.35(25) 1.776(20), 1.601(25) 1.9(25) 11.1(15), 3.39(25)

0.903(15), 0.725(30), 0.578(50) 0.119(20), 0.110(25) 0.703(0), 0.545(25), 0.444(50) 0.740(⫺25), 0.539(0)

0.332(20), 0.316(25) 3.07(10), 2.55(17) 0.711(20), 0.627(30) 2.909(0), 1.724(25), 1.129(50) 609(25), 114(50), 31.5(75) 0.455(0), 0.347(25), 0.273(50) 49.0(20), 8.5(60) 1.684(40), 1.376(55) 0.72(25) 0.926(20), 0.808(25), 0.571(50) 1.996(20) 0.321(⫺33.5) 0.894(15), 0.730(30) 1.154(20) 0.579(20)

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TABLE 5.16 Viscosity and Surface Tension of Various Organic Substances (Continued)

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Surface tension, mN · m⫺1 Substance cis,cis-1,3,5-Trimethylcyclohexane trans-1,3,5-Trimethylcyclohexane Trimethylene sulfide 3,5,5-Trimethyl-1-hexanol 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane Trimethyl phosphite 2,4,6-Trimethylpyridine Triphenylamine Triphenyl phosphite Tripropylamine Tripropylene glycol Tripropylene glycol butyl ether Tripropylene glycol ethyl ether Tripropylene glycol isopropyl ether Tripropylene glycol methyl ether Tris(m-tolyl) phosphite Tris( p-tolyl) phosphite Tri-o-tolyl phosphate Undecane Vinyl acetate o-Xylene m-Xylene p-Xylene

a

b

Liquid range, ⬚C

Viscosity, mN · s · m⫺2 0.632(20), 0.558(30)

36.3(20)

35.0(30)

22.46 20.55 27.18(20)

0.0895 0.0888 24.88(40)

46.2

0.0955

24.58 34(25) 28.8(25)

0.0878

⫺107.4 to 140.5

0.714(20), 0.624(30)

⫺73.2 to 95 ⬍ ⫺70 to 194 ⫺112.3 to 110 ⫺107.4 to 99.2 ⫺78 to 112 ⫺46 to 171 125 to 348 22 to 360 ⫺93.5 to 158 up to 273 up to 276

0.638(20), 0.607(25) 11.06(25) 0.598(20) 0.502(20) 0.61(20) 1.498(20)

28.2(25) 27.4(25)

56.1(25) 6.58(25) 5.17(25) 7.7(25)

⫺42 to 242.4

30.0(25)

40.9(20) 26.26 23.95(20) 32.51 31.23 30.69

6.95(45)

0.0901 22.54(30) 0.1101 0.1104 0.1074

11 to 410 ⫺25.6 to 196 ⫺93 to 73 ⫺25.2 to 145 ⫺47.9 to 139 13 to 138

5.96(25) 37.55(15), 9.132(45), 5.075(65) 35.52(15), 8.794(45), 5.017(65) 38.8(35), 16.8(55) 1.707(0), 1.098(25), 0.761(50) 0.421(20) 1.084(0), 0.760(25), 0.561(50) 0.795(0), 0.581(25), 0.445(50) 0.603(25), 0.457(50), 0.359(75)

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances

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The temperature in degrees Celsius at which the dielectric constant and dipole moment were measured is shown in this table in parentheses after the value. In some cases, the dipole moment was determined with the substance dissolved in a solvent, and the solvent used is also shown in parentheses after the temperature. The dielectric constant (permittivity) tabulated is the relative dielectric constant, which is the ratio of the actual electric displacement to the electric field strength when an external field is applied to the substance, which is the ratio of the actual dielectric constant to the dielectric constant of a vacuum. The table gives the static dielectric constant ⑀, measured in static fields or at relatively low frequencies where no relaxation effects occur. The dipole moment is given in debye units D. The conversion factor to SI units is 1 D ⫽ 3.33564 ⫻ 10⫺30 C · m. Alternative names for entries are listed in Table 1.15 at the bottom of each double page. List of Abbreviations B, benzene g, gas C, CCl4 Hx, hexane cHex, cyclohexane lq, liquid D, 1,4-dioxane Substance Acetaldehyde Acetaldehyde oxime Acetamide Acetanilide Acetic acid Acetic anhydride Acetone Acetonitrile Acetophenone (⫾)-erythro-2-Acetoxy-2-bromobutane (⫾)-threo-2-Acetoxy-2-bromobutane Acetyl bromide Acetyl chloride Acetylene Acrylonitrile Allene Allylamine Allyl alcohol Allyl isocyanate Allyl isothiocyanate Allyl nitrite 2-Aminoethanol 2-(2-Aminoethylamino)ethanol N-(2-Aminoethyl)-1,2-ethanediamine Aniline Benzaldehyde Benzaldehyde oxime (mp 30) (mp 128) Benzamide Benzene Benzeneacetonitrile Benzenesulfonyl chloride Benzenethiol Benzonitrile Benzophenone

Dielectric constant, ⑀ 21.8 (10), 21.0 (18) 4.70 (25) 67.6 (91) 6.20 (20) 23.3 (0), 22.45 (20) 21.0 (20), 20.7 (25), 17.6 (56) 36.64 (20), 26.6 (82) 17.44 (25), 8.64 (202) 7.268 (25) 7.414 (25) 16.2 (20) 16.9 (2), 15.8 (22) 2.484 (⫺77) 33.0 (20) 2.025 (⫺4) 19.7 (20) 15.15 (15) 17.2 (18) 9.12 (25) 31.94 (20), 37.72 (25) 21.81 (20) 12.62 (20) 7.06 (20), 5.93 (70) 19.7 (0), 17.85 (20) 3.8 (20)

2.292(15), 2.283 (20), 2.274 (25) 17.87 (26) 28.90 (50) 4.38 (25), 4.26 (30) 25.9 (20), 24.0 (40) 14.60 (18), 11.4 (50)

Dipole moment, D 2.75 0.830 (20, lq), 0.90 (25, B) 3.76 3.65 (25, B) 1.70 2.8 2.88 3.924 3.02

2.43 (20, B) 2.72 3.87 1.2 1.61 3.2 (20, B) 2.59 (25, D) 1.9 1.13 3.0 1.2 (25, B) 1.5 (25, B) 3.42 (25, B) 0 3.5 4.50 (20, B) 1.13 (25, lq), 1.19 (20, B) 4.18 3.09 (50, lq), 2.98 (25, B)

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Benzoyl bromide Benzoyl chloride Benzoyl fluoride Benzyl acetate Benzyl alcohol Benzylamine Benzyl benzoate Benzyl chloride Benzylethylamine Benzyl ethyl ether Benzyl formate N-Benzylmethylamine Biphenyl Bis(2-aminoethyl)amine Bis(2-chloroethyl) ether Bis(3-chloropropyl) ether Bis(2-ethoxyethyl) ether Bis(2-hydroxyethyl) ether Bis(2-hydroxyethyl)sulfide Bis(2-hydroxypropyl) ether Bis(2-methoxyethyl) ether (⫾)-Bornyl acetate 3-Bromoaniline 4-Bromoaniline 2-Bromoanisole 4-Bromoanisole Bromobenzene 1-Bromobutane (⫾)-2-Bromobutane 2-Bromobutanoic acid cis-2-Bromo-2-butene trans-2-Bromo-2-butene 1-Bromo-2-chlorobenzene 1-Bromo-3-chlorobenzene 1-Bromo-4-chlorobenzene 1-Bromo-2-chloroethane cis-1-Bromo-2-chloroethene trans-1-Bromo-2-chloroethene Bromochlorodifluoromethane Bromochloromethane 3-Bromo-1-chloro-2-methylpropane Bromocyclohexane 1-Bromodecane Bromodichloromethane 1-Bromododecane Bromoethane 1-Bromo-2-ethoxypentane 2-Bromo-3-ethoxypentane 3-Bromo-2-ethoxypentane 1-Bromo-2-ethylbenzene 1-Bromo-3-ethylbenzene 1-Bromo-4-ethylbenzene

Dielectric constant, ⑀ 21.33 (20), 20.74 (25) 29.0 (0), 23 (23) 22.7 (20) 5.1 (21), 5.34 (930) 13.0 (20), 11.92 (30), 9.5 (70) 5.5 (1), 5.18 (20) 5.26 (30) 7.0 (13), 6.85 (25) 4.3 (20) 3.90 (25) 6.34 (30) 4.4 (19) 2.53 (75) 12.62 (20) 21.20 (20) 10.10 (20) 31.69 (20) 28.61 (20) 20.38 (20) 7.23 (25) 4.6 (21) 13.0 (20) 7.06 (30) 8.96 (30) 7.40 (30) 5.45 (20), 5.40 (25) 7.88 (⫺10), 7.32 (10), 7.07 (20) 8.64 (25) 7.2 (20) 5.38 (20) 6.76 (20) 6.80 (20) 4.58 (20) 7.41 (10) 7.31 (17) 2.50 (17) 3.92 (⫺150) 7.79 8.90 (30) 11 (⫺65), 8.003(30) 4.75 (1), 4.44 (25) 4.07 (25) 13.6 (⫺60), 9.39 (20), 9.01 (25) 6.45 (25) 6.40 (25) 8.24 (25) 5.55 (25) 5.56 (25) 5.42 (25)

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Dipole moment, D 3.40 (20, B) 3.16 (25, B) 1.80 (25, B) 1.71 1.15 (20, lq), 1.38 (25, B) 2.06 (30, B) 1.83 (20, B)

0 2.6 1.92 (25, B) 2.31 (20, B)

1.89 (22) 2.67 (20, B) 2.88 (25, B)

1.70 2.08 2.23

2.15 (20, B) 1.52 (22, B) 0.1 (25, B) 1.09

1.66 (25, B) 1.08 (25, lq), 2.3 (25, B) 2.08 (20, lq), 1.90 (25, lq) 1.31 (25, B) 2.01 (25, lq), 1.89 (25, B) 2.03 (g), 2.04 (20, lq) 2.32 (25, B) 2.07 (25, B) 2.15 (25, B)

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Bromoethylene 1-Bromo-2-fluorobenzene 1-Bromo-3-fluorobenzene 1-Bromo-4-fluorobenzene Bromoform 1-Bromoheptane 2-Bromoheptane 3-Bromoheptane 4-Bromoheptane 1-Bromohexadecane 1-Bromohexane Bromomethane (Bromomethyl)benzene 1-Bromo-3-methylbutane 2-Bromo-2-methylbutane 2-Bromo-3-methylbutanoic acid 1-Bromo-2-methylpropane 2-Bromo-2-methylpropane 1-Bromonaphthalene 3-Bromonitrobenzene 1-Bromononane 1-Bromooctane 1-Bromopentadecane 1-Bromopentane 3-Bromopentane 1-Bromopropane 2-Bromopropane 2-Bromopropanoic acid 3-Bromopropene 2-Bromopyridine 1-Bromotetradecane o-Bromotoluene m-Bromotoluene p-Bromotoluene Bromotrichloromethane Bromotrifluoromethane 1-Bromoundecane 1,3-Butadiene Butanal Butane 1,2-Butanediol 1,3-Butanediol 1,4-Butanediol 1,3-Butanediol dinitrate 2,3-Butanediol dinitrate 1,3-Butanedione Butanenitrile Butanesulfonyl chloride 1,2,3,4-Butanetetrol 1-Butanethiol 2-Butanethiol Butanoic acid

Dielectric constant, ⑀ 5.63 (5), 4.78 (25) 4.72 (25) 4.85 (25) 2.60 (25) 4.39 (20) 5.33 (25), 4.48 (90) 6.46 (22) 6.93 (22) 6.81 (22) 3.71 (25) 6.30 (1), 5.82 (25) 9.82 (0), 9.71 (3), 1.0068 (100, g) 6.658 (20) 8.04 (⫺56), 6.33 (18) 9.21 (25) 6.5 (20) 10.98 (20), 7.2 (25) 10.98 (20) 5.83 (25), 5.12 (20) 20.2 (55) 5.42 (⫺20), 4.74 (25) 6.35 (⫺50) 3.9 (20) 9.9 (⫺90), 6.32 (25) 8.37 (25) 8.09 (20) 9.46 (20) 11.0 (21) 7.0 (20) 23.18 (25) 3.84 (25) 4.64 (20), 4.28 (58) 5.566 (20), 5.36 (58) 5.503 (20), 5.49 (58) 2.40 (20) 3.73 (⫺150) 4.73 (⫺9) 2.050 (⫺8) 13.45 (25) 1.7697 (22) 22.4 (25) 28.8 (25) 33 (15), 31.9 (25), 30 (38) 18.85 (20) 28.85 (20) 4.04 (25) 24.83 (20) 28.2 (120) 5.20 (15), 5.07 (25), 4.59 (50) 5.645 (15) 2.97 (20)

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Dipole moment, D 1.42

1.00, 0.92 (25, lq) 2.17, 2.02 (20, lq) 2.08 (20, B) 2.06 (20, B) 2.06 (20, B) 1.98 (20, lq), 1.96 (25, C) 2.06 (20, lq) 1.82 1.95 (20, B)

1.92 (25, lq), 1.99 (20, B) 1.29 (25, lq) 1.95 (25, lq) 1.99 (20, lq), 1.88 (25, lq) 2.20 2.18 2.21 1.9 1.92 (20, lq), 1.83 (25, lq) 1.45 (20, B) 1.77 (20, B) 1.95 (20, B) 0.65 0.403 2.72 0

4.07

4.07 3.94 (25, D) 1.54 (25, lq or B) 1.65 (30, B)

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Butanoic anhydride 1-Butanol (⫾)-2-Butanol 2-Butanone 2-Butanone oxime trans-2-Butenal 1-Butene cis-2-Butene trans-2-Butene 3-Butenenitrile 2-Butoxyethanol Butoxyethyne N-Butylacetamide N-sec-Butylacetamide Butyl acetate sec-Butyl acetate tert-Butyl acetate tert-Butylacetic acid Butyl acrylate Butylamine sec-Butylamine tert-Butylamine Butylbenzene sec-Butylbenzene tert-Butylbenzene Butyl butanoate Butyl ethyl ether Butyl formate Butyl isocyanate Butyl methyl ether 2-tert-Butyl-4-methylphenol Butyl nitrate tert-Butyl nitrite Butyl oleate N-Butylpropanamide Butyl propanoate 4-tert-Butylpyridine Butylsilane Butyl stearate Butyl trichloroacetate Butyl vinyl ether 4-Butyrolactone Camphor Carbon disulfide Carbon tetrachloride Carbon tetrafluoride D-(⫹)-Carvone Chloroacetic acid o-Chloroaniline m-Chloroaniline p-Chloroaniline Chlorobenzene

Dielectric constant, ⑀ 12.8 (20) 17.84 (20), 8.2 (118) 17.26 (20), 16.6 (25) 18.56 (20), 15.3 (60) 3.4 (20) 2.2195 (⫺53), 1.0032 (20, g) 1.960 (23) 28.1 (20) 9.43 (25) 6.62 (25) 104.0 (20) 100.0 (100) 6.85 (⫺73), 5.07 (20) 5.135 (20) 5.672 (20) 2.85 (23) 5.25 (28) 4.71 (20) 4.4 (21) 2.36 (20) 2.36 (20) 2.36 (20) 4.39 (25) 6.10 (30), 2.43 (80) 12.29 (20)

13.10 (20) 11.47 (25) 4.00 (25) 100.6 (25) 4.838 (20) 2.537 (20) 3.11 (30) 7.480 (20) 39.0 (20) 11.35 (20) 3.0 (⫺112), 2.64 (20) 2.24 (20), 2.228 (25) 1.0006 (25, g) 11 (22) 20 (20), 12.35 (65) 13.40 (20) 13.3 (20) 5.69 (20), 4.2 (120)

cap height base of text

Dipole moment, D

1.66 1.66 (30, B) 2.78 3.67 0.438 0.253 0 4.53 2.08 (25, B) 2.05 (25, lq)

1.86 (22, B) 1.9 1.91 (25, B)

1.00 1.28 (25, B) 1.29 (25, B) 0 0 0.83 1.24 2.08 (26, lq), 2.03 (25, B) 1.25 (25, B) 1.31 (20, B) 2.99 (20, B)

1.79 (23, B) 2.87 (25, C) 1.88 (24, B) 1.25 (25, Hx) 4.27 2.91 (20, B), 3.10 (25, B) 0 0 0 2.8 (15, B) 2.31 (30, B) 1.78 (20, B) 2.68 (20, B) 2.99 (25, B) 1.69

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PHYSICAL PROPERTIES

TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance 2-Chloro-1,3-butadiene 1-Chlorobutane 2-Chlorobutane Chlorocyclohexane Chlorodifluoromethane 2-Chloro-N,N-dimethylacetamide 1-Chlorododecane 1-Chloro-2,3-epoxypropane Chloroethane 2-Chloroethanol (2-Chloro)ethylbenzene (3-Chloro)ethylbenzene (4-Chloro)ethylbenzene 2-Chlorofluorobenzene 3-Chlorofluorobenzene 4-Chlorofluorobenzene Chloroform 1-Chloroheptane 2-Chloroheptane 3-Chloroheptane 4-Chloroheptane 1-Chlorohexane 6-Chloro-1-hexanol 1-Chloro-2-isocyanatoethane Chloromethane 1-Chloro-3-methylbutane 2-Chloro-2-methylbutane 4-Chloromethyl-1,3-dioxolan-2-one Chloromethyl methyl ether (Chloromethyl)oxirane 1-Chloro-2-methylpropane 2-Chloro-2-methylpropane 1-Chloronaphthalene o-Chloronitrobenzene m-Chloronitrobenzene p-Chloronitrobenzene 2-Chloro-2-nitropropane 4-Chloro-3-nitrotoluene 1-Chlorooctane Chloropentafluoroethane 1-Chloropentane o-Chlorophenol m-Chlorophenol p-Chlorophenol 1-Chloropropane 2-Chloropropane 3-Chloro-1,2-propanediol 3-Chloro-1,2-propanediol dinitrate 3-Chloro-1-propanol 1-Chloro-2-propanol 1-Chloro-2-propanone 2-Chloro-1-propene

Dielectric constant, ⑀ 4.914 (20) 9.07 (⫺30), 7.276 (20) 8.564 (20), 7.09 (30) 10.9 (⫺47), 7.951 (30) 6.11 (24) 39.2 (25) 4.2 (20) 25.6 (1), 22.6 (22) 1.013 (19, g), 9.45 (20) 25.80 (20), 13 (132) 4.36 (25) 5.18 (25) 5.16 (25) 6.10 (25) 4.96 (25) 3.34 (25) 4.807 (25), 4.31 (50) 5.52 (20) 6.52 (22) 6.70 (22) 6.54 (22) 6.104 (20) 21.6 (⫺31) 29.1 (15) 1.0069 (g), 12.6 (⫺20), 10.0 (22) 7.63 (⫺70), 6.05 (20) 12.31 (⫺50) 97.5 (40) 22.6 (20) 7.87 (⫺38), 7.027 (20) 10.95 (0), 9.66 (20) 5.04 (25) 37.7 (50), 32 (80) 20.9 (50), 18 (80) 8.09 (120) 31.9 (⫺23) 28.07 (28) 5.05 (25) 6.654 (20) 7.40 (21), 6.31 (25) 6.255 (20) 11.18 (41) 8.59 (20) 9.82 (20) 31.0 (20) 17.50 (20) 36.0 (⫺58) 59.0 (⫺120) 30 (19) 8.92 (26)

top of rh base of rh cap height base of text

Dipole moment, D

2.05 (g), 2.0 (20, B) 2.04 (g), 2.1 (20, B) 2.2 (25, B) 1.42 (g) 2.11 (25, lq), 1.94 (20, B) 1.8 (25, C) 2.05 1.78

1.04 1.86 (22, B) 2.05 (22, B) 2.06 (22, B) 2.06 (22, B) 1.94 (20, B)

1.892 1.94 (20, B)

1.88 (C) 1.8 2.00 2.13 1.33 (25, lq), 1.52 (25, B) 4.64 3.73 2.83

2.14 (25, lq) 0.52 2.16 2.19 2.19 (25, B) 2.11 2.05 2.17

2.22 (g), 2.37 (20, Hx) 1.647

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance 3-Chloro-1-propene 2-Chloropyridine 4-Chlorothiophenol o-Chlorotoluene m-Chlorotoluene p-Chlorotoluene Chlorotrifluoromethane 2-Chloro-1-trifluoromethyl-5nitrobenzene 4-Chloro-1-trifluoromethyl-3nitrobenzene 3-Chloro-1,1,1-trifluoropropane Chlorotrimethylsilane Cineole Cinnamaldehyde o-Cresol m-Cresol p-Cresol Crotonic acid Cyanoacetic acid Cyanoacetylene 2-Cyanopyridine 3-Cyanopyridine 4-Cyanopyridine Cyclobutanone Cycloheptane Cycloheptanone 1,3-Cyclohexadiene 1,4-Cyclohexadiene Cyclohexane Cyclohexanecarboxylic acid 1,4-Cyclohexanedione Cyclohexanethiol Cyclohexanol Cyclohexanone Cyclohexanone oxime Cyclohexene Cyclohexylamine Cyclohexylbenzene Cyclohexylmethanol Cyclohexyl nitrite o-Cyclohexylphenol p-Cyclohexylphenol Cyclooctane cis-Cyclooctene Cyclopentane Cyclopentanecarbonitrile Cyclopentanol Cyclopentanone Cyclopentene p-Cymene cis-Decahydronaphthalene

Dielectric constant, ⑀ 8.2 (20) 27.32 (20) 3.59 (65) 4.72 (20), 4.2 (55) 5.76 (20), 5.0 (60) 6.25 (20), 5.6 (55) 1.0013 (29, g), 3.01 (⫺150) 9.8 (30)

cap height base of text

Dipole moment, D 1.94

1.56 1.77 (20, lq), 1.8 (22, B) 2.21 0.50

12.8 (30) 7.32 (22) 2.09 (20, B) 4.57 (25) 17 (20), 16.9 (24) 6.76 (25) 12.44 (25) 13.05 (25) 33.4 (4) 72.3 (19) 93.77 (30) 20.54 (50) 5.23 (80) 14.27 (25) 2.078 (30) 13.16 (25) 2.68 (⫺89) 2.211 (23) 2.05 (15), 2.02 (25) 2.6 (31) 15.0 (25), 4.40 (78) 5.420 (25) 16.40 (20), 15.0 (25), 7.24 (100) 20 (⫺40), 16.1 (20) 3.04 (89) 2.6 (⫺105), 2.218 (20) 4.55 (20) 9.7 (60), 8.1 (80) 9.33 (25) 3.97 (55) 4.42 (131) 2.116 (22) 2.306 (23) 1.9687 (20) 22.68 (20) 25 (⫺20), 18.5 (10) 16 (⫺51), 13.58 (25) 2.083 (22) 2.243 (20), 2.23 (25) 2.22 (20)

3.74 1.45 (25, B) 1.61 (25, B) 1.54 (20, B) 2.13 (30, B) 3.724

2.89

0.38 (20, B) 0 1.41 1.86 (25, C) 2.87 0.83 (25, B) 0.332 1.22 (20, lq), 1.26 (20, B) 0 1.68 (20, B)

0 0 1.72 (25, C) 3.30 0.20 0 0

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance trans-Decahydronaphthalene Decamethylcyclopentasiloxane Decamethyltetrasiloxane Decane 1-Decanol 1-Decene meso-2,3-Diacetoxybutane Diallyl sulfide Dibenzofuran Dibenzylamine Dibenzyl decanedioate Dibenzyl ether o-Dibromobenzene m-Dibromobenzene p-Dibromobenzene 1,2-Dibromobutane 1,3-Dibromobutane 1,4-Dibromobutane 2,3-Dibromobutane meso-2,3-Dibromobutane (⫾)-2,3-Dibromobutane 1,2-Dibromodichloromethane 1,2-Dibromodifluoromethane 1,2-Dibromoethane cis-1,2-Dibromoethylene trans-1,2-Dibromoethylene Dibromomethane cis-1,2-Dibromoethylene trans-1,2-Dibromoethylene 1,2-Dibromoheptane 2,3-Dibromoheptane 3,4-Dibromoheptane meso-3,4-Dibromohexane (⫾)-3,4-Dibromohexane 1,6-Dibromohexane Dibromomethane 1,2-Dibromo-2-methylpropane 1,2-Dibromopentane (⫾)-erythro-2,3-Dibromopentane (⫾)-threo-2,3-Dibromopentane 1,4-Dibromopentane 1,5-Dibromopentane 1,2-Dibromopropane 1,3-Dibromopropane Dibromotetrafluoroethane Dibutylamine Dibutyl decanedioate Dibutyl ether Dibutyl maleate Dibutyl o-phthalate Dibutyl sulfide Dichloroacetic acid

Dielectric constant, ⑀ 2.18 (20) 2.5 (20) 2.4 (20) 1.991 (20), 1.844 (130) 8.1 (20) 2.14 (20) 6.644 (25) 4.9 (20) 3.0 (100) 3.6 (20) 4.6 (25) 3.82 (20) 7.86 (20) 4.21 (20) 2.57 (95) 4.74 (20) 9.14 (20) 8.68 (30) 6.36 (20), 5.75 (25) 6.245 (25) 5.758 (25) 2.54 (25) 2.94 (0) 4.96 (20), 4.78 (25), 4.09 (131) 7.08 (25) 2.88 (25) 7.77 (10) 7.7 (0), 7.08 (25) 2.9 (0), 2.88 (25) 3.8 (25) 5.1 (25) 4.7 (25) 4.67 (25) 6.732 (25) 8.52 (25) 7.77 (10), 6.7 (40) 4.1 (20) 4.39 (25) 5.43 (25) 6.507 (25) 9.05 (20) 9.14 (30) 4.60 (10), 4.3 (20) 9.48 (20) 2.34 (25) 2.78 (20) 4.54 (20) 3.08 (20) 6.58 (20), 6.436 (30), 5.99 (45) 4.29 (25) 8.33 (20), 7.8 (61)

top of rh base of rh cap height base of text

Dipole moment, D 0 0.79 (25, lq) 0 1.71 (20, B), 1.62 (25, B) 0 1.33 (25, B) 0.88 (25, B) 0.97 (20, lq), 1.02 (20, B) 1.39 (21, B) 2.13 (20, B) 1.5 (20, B) 0

2.16 (20, lq), 2.06 (20, B) 2.20

0.66 1.11

1.43 1.35 (B) 0 1.78 (25, D) 2.15 (25, B) 2.15 (25, B)

1.43

1.13

1.06 (20, lq), 1.05 (20, B) 2.64 (25, B) 1.18 2.70 (25, B) 2.97 (20, lq), 2.85 (30, B) 1.6

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Dichloroacetic anhydride 1,1,-Dichloroacetone o-Dichlorobenzene m-Dichlorobenzene p-Dichlorobenzene 1,2-Dichlorobutane 1,4-Dichlorobutane Dichlorodifluoromethane 4-Chloro-1,3-dioxalan-2-one 4,5-Dichloro-1,3-dioxalan-2-one 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene 2,2⬘-Dichloroethyl ether Dichlorofluoromethane 1,6-Dichlorohexane Dichloromethane 1,3-Dichloroisopropyl nitrate (Dichloromethyl)benzene Dichloromethyl isocyanate 1,2-Dichloro-2-methylpropane 2,4-Dichloro-1-nitrobenzene 1,1-Dichloro-1-nitroethane 1,2-Dichloropentane 1,5-Dichloropentane 2,4-Dichlorophenol 1,2-Dichloropropane 1,3-Dichloropropane 2,2-Dichloropropane 1,1-Dichloro-2-propanone 1,2-Dichlorotetrafluoroethane 2,4-Dichlorotoluene 2,6-Dichlorotoluene 3,4-Dichlorotoluene Diethanolamine 1,1-Diethoxyethane 1,2-Diethoxyethane Diethoxymethane N,N-Diethylacetamide N,N-Diethylacetoacetamide Diethylamine N,N-Diethylaniline Diethyl carbonate N,N-Diethyl-N⬘,N⬘-dimethylurea Diethyl decanedioate Diethylene glycol Diethylene glycol diethyl ether Diethyl ether Diethyl ethyl phosphonate N,N-Diethylformamide

Dielectric constant, ⑀ 15.8 (25) 14.6 (20) 10.12 (20), 9.93 (25), 7.10 (90) 5.02 (20), 5.04 (25), 4.22 (90) 2.394 (55) 7.74 (25) 9.30 (35) 3.50 (⫺150), 2.13 (29) 62.0 (40) 31.8 (40) 10.10 (20) 12.7 (⫺10), 10.42 (20) 4.60 (20), 4.60 (25) 9.20 (25) 2.14 (20) 21.2 (20) 5.34 (28) 8.60 (35) 9.14 (20), 8.93 (25), 1.0065 (100, g) 13.28 (20) 6.9 (20) 7.36 (15) 7.15 (23) 13.06 (28) 16.3 (30) 6.89 (20) 9.92 (25) 8.37 (20), 8.93 (26), 7.90 (35) 10.27 (30) 11.37 (20) 14 (20) 2.48 (0), 2.26 (25) 5.68 (28) 3.36 (28) 9.39 (28) 25.75 (20) 3.80 (25) 3.90 (20) 2.527 (20) 32.1 (20) 40.8 (25) 3.680 (20) 5.5 (19) 2.82 (24) 17.89 (25) 5.0 (30) 3.182 (20) 5.70 4.267 (20), 3.97 (40) 11.00 (15), 9.86 (45) 29.6 (20)

cap height base of text

Dipole moment, D

2.50 1.72 0 2.22 0.51

2.06 1.48 1.34 1.90 0 2.61 (20, B) 1.29 (g) 1.60 2.1

1.60 (25, B) 1.87 (25, B) 2.08 2.62 0.53 1.7 3.0 2.84 (25, B) 1.08 1.99 (20, B), 1.65 (25, B)

0.92 1.40 (20, lq), 1.80 (20, B) 1.10 2.38 (20, lq), 2.52 (20, B) 2.3 1.15 2.95 (32, lq), 2.91 (20, C)

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PHYSICAL PROPERTIES

TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Diethyl fumarate Diethyl glutarate Diethyl glycol Di(2-ethylhexyl) o-phthalate Diethyl maleate Diethyl methanephosphate Diethyl 1,3-propanedioate (malonate) Diethyl nonanedioate Diethyl oxalate Diethyl o-phthalate Diethylsilane Diethyl succinate Diethyl sulfate Diethyl sulfide Diethyl sulfite Diethylzinc o-Difluorobenzene m-Difluorobenzene 1,1-Difluoroethane Difluoromethane 2,3-Dihydropyran 1,2-Dihydroxybenzene 1,3-Dihydroxybenzene 1,4-Dihydroxybenzene 1,2-Diiodobenzene 1,3-Diiodobenzene 1,4-Diodobenzene cis-1,2-Diiodoethylene trans-1,2-Diiodoethylene Diiodomethane Diisobutylamine 1,6-Diisocyanatohexane Diisopentylamine Diisopentyl ether Diisopropylamine Diisopropyl ether 1,2-Dimethoxybenzene Dimethoxydimethylsilane 1,2-Dimethoxyethane Dimethoxymethane N,N-Dimethylacetamide 2-Dimethylamino-2-methyl-1propanol Dimethylamine N,N-Dimethylaniline 2,4-Dimethylaniline 2,3-Dimethyl-1,3-butadiene N,N-Dimethylbutanamide 2,2-Dimethylbutane 2,3-Dimethylbutane 3,3-Dimethyl-2-butanone

Dielectric constant, ⑀ 6.56 (23) 6.7 (30) 31.82 (20) 5.3 (20), 4.91 (35), 4.77 (45) 8.58 (23), 7.56 (25) 13.405 (40) 8.03 (25), 7.55 (31) 5.13 (30) 8.266 (20) 7.34 (35), 7.13 (45) 2.544 (20) 6.098 (20) 29.2 (20) 5.72 (25), 5.24 (50) 15.6 (20), 14 (50) 2.55 (20) 13.38 (28) 5.01 (28) 53.74 (⫺121) 5.136 (35) 17.57 (115) 13.55 (120) 5.7 (20), 5.41 (50) 4.3 (25), 4.11 (50) 2.88 (120) 4.46 (72) 3.19 (77) 5.316 (25) 2.7 (22) 14.41 (15) 2.5 (18) 2.82 (20) 3.88 (25), 3.805 (30) 4.45 (20), 4.09 (25) 3.663 (25) 7.60 (10), 7.30 (23.5) 2.644 (20) 38.85 (21), 37.78 (25) 12.36 (25) 6.32 (0), 5.26 (25) 4.90 (25), 4.4 (70) 4.9 (20) 2.102 (20) 29.7 (20) 1.869 (20) 1.889 (20) 12.73 (20)

top of rh base of rh cap height base of text

Dipole moment, D 2.40 (20, B) 2.46 (30, lq) 2.8 2.56 (25, B) 2.49 (20, lq), 2.54 (25, B)

2.49 (20, D) 2.8 (25, B) 2.3 4.46 (25, D) 1.54 0.62 (25, B) 2.46 1.51 2.27 1.978 2.60 (25, B) 2.09 (44, B) 1.4 (44, B) 1.70 (20, B) 1.22 (20, B) 0.19 (20, B) 0.71 (B) 0 1.08 (25, B) 1.10 (25, B) 1.48 (30, B) 0.98 (20, lq), 1.23 (25, B) 1.26 (25, B) 1.13 1.32 (25, B) 1.71 (25, B) 0.74 3.80

1.01 1.68 1.40 (25, B)

0 0

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance 2,2-Dimethyl-1-butanol Dimethyl carbonate cis-1,2-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane 1,1-Dimethylcyclopentane Dimethyl disulfide Dimethyl ether N,N-Dimethylformamide 2,4-Dimethylheptane 2,5-Dimethylheptane 2,6-Dimethylheptane 2,6-Dimethyl-4-heptanone 2,2-Dimethylhexane 2,5-Dimethylhexane 3,3-Dimethylhexane 3,4-Dimethylhexane Dimethyl hexanedioate 1,3-Dimethylimidazolidin-2-one Dimethyl maleate Dimethyl malonate Dimethyl methanephosphate N,N-Dimethyl methanesulfonamide 1,2-Dimethylnaphthalene 1,6-Dimethylnaphthalene 4,4-Dimethyloxazolidine-2-one N,N-Dimethylpentanamide 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane Dimethyl pentanedioate 2,4-Dimethyl-3-pentanone 2,3-Dimethylphenol 2,4-Dimethylphenol 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol 3,5-Dimethylphenol Dimethyl o-phthalate 2,2-Dimethylpropanal N,N-Dimethylpropanamide 2,2-Dimethylpropanamide 2,2-Dimethylpropane 2,2-Dimethylpropane nitrile N,N-Dimethylpropanamide 2,2-Dimethyl-1-propanol 2,5-Dimethylpyrazine 2,6-Dimethylpyrazine 2,4-Dimethylpyridine 2,6-Dimethylpyridine 2,6-Dimethylpyridine-1-oxide 2,3-Dimethylquinoxaline

Dielectric constant, ⑀ 10.5 (20) 3.087 (25) 2.06 (25) 2.04 (25) 9.6 (25) 6.18 (⫺15), 5.02 (25), 2.97 (110) 38.25 (20), 36.71 (25) 1.9 (20) 1.9 (20) 2 (20) 9.91 (20) 1.95 (20) 1.96 (21) 1.96 (20) 1.98 (19) 6.84 (20) 37.60 (25) 9.82 (20) 22.3 (20) 80.4 (50) 2.61 (25) 2.73 (20) 39.2 (60) 26.4 (20) 1.915 (20) 1.929 (20) 1.902 (20) 1.942 (20) 7.87 (20)

cap height base of text

Dipole moment, D

0.90 0 0 0 1.8 1.30 3.82 (25, B) 0 0 0 2.66 (25, C) 0 0 0 0 2.28 (20, B) 2.48 (25, C) 2.41 (20, B)

0 0

0 0 0 0 2.7

4.81 (70) 5.06 (30) 5.36 (65) 4.90 (40) 9.02 (60) 9.06 (50) 8.66 (20), 8.25 (25), 8.11 (45) 9.051 (20) 34.6 (20) 20.13 (25) 1.769 (23), 1.678 (98) 21.1 (20) 33.1 8.35 (60) 2.436 (20) 2.653 (35) 9.60 (20) 7.33 (20) 46.11 (25) 2.3 (25)

1.48 (20, B), 1.98 (60, B) 1.43 (20, B), 1.52 (60, B) 1.4 1.77 (20, B) 1.76 (20, B) 2.8 (25, B) 2.66

0 3.95

0 2.3 1.7 0

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PHYSICAL PROPERTIES

TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Dimethyl succinate Dimethyl sulfate Dimethyl sulfide Dimethyl sulfite Dimethyl sulfone Dimethyl sulfoxide cis-2,5-Dimethyltetrahydrofuran N,N-Dimethylthioformamide N,N-Dimethyl-o-toluidine N,N-Dimethyl-p-toluidine m-Dinitrobenzene 2,2-Dinitropropane Dinonyl hexanedioate Dinonyl o-phthalate Dioctyl decanedioate Dioctyl o-phthalate 1,4-Dioxane 1,3-Dioxolane 1,3-Dioxolan-2-one Dipentene Dipentyl ether Dipentyl o-phthalate Dipentyl sulfide Dipentylamine 1,2-Diphenylethane Diphenyl ether Diphenylmethane Dipropylamine Dipropyl ether N,N-Dipropylformamaide Dipropyl sulfone Dipropyl sulfoxide Divinyl ether Dodecamethylcyclohexasiloxane Dodecamethylpentasiloxane Dodecane 1-Dodecanol 1-Dodecene 6-Dodecyne 1,2-Epoxybutane Erythritol Ethane 1,2-Ethanediamine 1,2-Ethanediol 1,2-Ethanediol diacetate 1,2-Ethanediol dinitrate 1,2-Ethanediol monoacetate 1,2-Ethanedithiol Ethanesulfonyl chloride Ethanethiol Ethanol Ethanolamine

Dielectric constant, ⑀ 7.19 (20) 55.0 (25) 6.70 (21) 22.5 (23) 47.39 (110) 47.24 (20), 41.9 (55) 5.03 (23) 47.5 (25) 3.4 (20) 3.9(20) 22.9 (92) 42.4 (52)

top of rh base of rh cap height base of text

Dipole moment, D 2.09 (20, B) 4.31 (25, D) 1.554 2.93 (20, B) 3.96 (25, B)

0.88 (25, B) 1.29 (25, B)

2.53 (25, B) 4.65 (35), 4.52 (45) 4.0 (27) 5.1 (25) 2.219 (20), 2.21 (25) 89.78 (40) 2.38 (25) 2.80 (25) 5.79 (35), 5.62 (45) 3.83 (25) 3.3 (52) 2.4 (110) 3.73 (10), 3.63 (30) 2.7 (18), 2.57 (26) 2.923 (20) 3.38 (24) 23.5 (20) 32.62 (30) 30.37 (30) 3.94 (15) 2.6 (20) 2.5 (20) 2.05 (⫺10), 2.01 (20) 5.15 (20), 6.5 (25) 2.15 (20) 2.17 (25)

3.06 (25, C) 0 1.19

0.98 (20, lq), 1.24 (25, B) 2.71 (20, lq) 1.59 (25, B) 1.31 (20, C), 1.01 (25, B) 0 (110, lq), 0.45 (25, B) 1.3 0.26 (30, lq), 0.3 (25, B) 1.01 (20, lq), 1.03 (20, B) 1.21

0.78

0 1.52 (20, B) 0 2.01 (20, B)

28 (128) 1.936 (⫺178), 1.0015 (0) 16.8 (18), 13.82 (20) 41.4 (20), 37.7 (25) 7.7 (17) 28.26 (20) 12.95 (30) 7.26 (20) 6.9 (15), 6.667 (25) 25.3 (20), 20.21 (55) 31.94 (20)

0 1.96 2.28 2.34 (30, B)

3.89 (25, B) 1.58 1.69

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance

Dielectric constant, ⑀

Ethoxyacetylene 4-Ethoxyaniline Ethoxybenzene (phenetol) 2-Ethoxyethanol 2-Ethoxyethyl acetate 1-Ethoxy-2-methylbutane 1-Ethoxynaphthalene 1-Ethoxypentane ␣-Ethoxytoluene Ethoxytrimethylsilane N-Ethylacetamide Ethyl acetate Ethyl acetoacetate

8.05 (25) 7.43 (25) 4.216 (20) 13.38 (25) 7.567 (30) 3.96 (20) 3.3 (19) 3.6 (23) 3.9 (20) 3.013 (25) 135.0 (20) 6.081 (20), 5.30 (77) 14.0 (20)

Ethyl acrylate Ethylamine N-Ethylaniline 4-Ethylaniline Ethylbenzene Ethyl benzoate Ethyl 2-bromoacetate Ethyl ␣-bromobutanoate Ethyl 2-bromo-2-methylpropanoate Ethyl 2-bromopropanoate N-Ethylbutanamide Ethyl butanoate 2-Ethylbutanoic acid 2-Ethyl-1-butanol Ethyl tert-butyl ether Ethyl carbamate Ethyl chloroacetate Ethyl chlorocarbonate Ethyl cis-3-chlorocrotonate Ethyl trans-3-chlorocrotonate Ethyl chloroformate Ethyl 2-chloropropanoate Ethyl 3-chloropropanoate Ethyl trans-cinnamate Ethyl crotonate Ethyl cyanoacetate Ethylcyclobutane Ethylcyclohexane Ethylcyclopropane Ethyl dichloroacetate Ethyl dodecanoate Ethylene Ethylene carbonate Ethylenediamine Ethylene dinitrate 2,2⬘-(Ethylenedioxy)diethanol Ethylene glycol Ethylene glycol diacetate

6.05 (30) 8.7 (0), 6.94 (10) 5.87 (20) 4.84 (25) 2.446 (20) 6.20 (20) 8.75 (30) 8 (20) 8.55 (30) 9.4 (20), 8.57 (30) 107.0 (25) 5.18 (28) 2.72 (23) 6.19 (90) 7.07 (25) 14.2 (50), 14.14 (55) 11.4 (21) 9.736 (36) 7.67 (76) 4.70 (54) 11 (20) 11.95 (30) 10.19 (30) 6.1 (18), 5.83 (20) 5.4 (20) 31.62 (⫺10), 26.9 (20) 1.965 (20) 2.054 (20) 1.933 (20) 12 (2), 10 (22) 3.4 (20), 2.7 (143) 1.001 44 (0, g), 1.483 (⫺3) 89.78 (40), 69.4 (91) 13.82 (20) 28.3 (20) 23.69 (20) 41.4 (20), 37.7 (25) 7.7 (17)

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Dipole moment, D

1.45 2.24 (30, B) 2.25 (30, B)

1.78 3.22 (18, B, keto form) 2.04 (⫺80, CS2, enol form) 2.0 1.22

0.59 2.00 2.40 (25, B)

1.74 (22, B)

2.59 (30, D) 2.65 (25, B)

2.56 (35, B)

1.86 (20, B) 1.95 (24, B) 2.2 0 2.63 (25, B) 1.3 (20, lq) 0 4.87 (25, B) 1.98 3.58 (25, B) 5.58 (lq) 2.28

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Ethyleneimine Ethylene oxide Ethylene sulfite N-Ethylformamide Ethyl formate Ethyl fumarate Ethyl furan-2-carboxylate Ethylhexadecanoate 3-Ethylhexane 2-Ethyl-1,2-hexanediol Ethyl hexanoate 2-Ethyl-1-hexanol 2-Ethylhexyl acetate Ethyl 2-iodopropanoate Ethyl isocyanate Ethyl isopentyl ether Ethyl isothiocyanate Ethyl lactate Ethyl maleate Ethyl methacrylate Ethyl 3-methylbutanoate Ethyl-N-methyl carbamate Ethyl methyl carbonate Ethyl methyl ether 3-Ethyl-2-methylpentane Ethyl nitrate Ethyl 9-octadecanoate 3-Ethyloxazolidine-2-one 4-Ethyloxazolidine-2-one Ethyl 4-oxopentanoate 3-Ethylpentane Ethyl pentanoate 3-Ethyl-3-pentanol Ethyl pentyl ether Ethyl phenylacetate Ethyl phenyl sulfide N-Ethyl propanamide Ethyl propanoate Ethyl propyl ether 2-Ethylpyridine 4-Ethylpyridine Ethyl salicylate Ethyl stearate Ethyl thiocyanate p-Ethyltoluene Ethyl trichloroacetate Ethyltrimethylsilazine Ethyl vinyl ether Fluorobenzene 4-Fluorobenzene sulfonylchloride 2-Fluoroiodobenzene 3-Fluoroiodobenzene

Dielectric constant, ⑀ 18.3 (25) 14 (⫺1), 12.42 (20) 39.6 (25) 102.7 (25) 8.57 (15), 7.16 (25) 6.5 (23) 9.02 (20) 3.2 (20), 2.71 (104) 1.96 (20) 18.73 (20) 4.45 (20) 7.58 (25), 4.41 (90) 8.6 (20) 19.7 (20) 3.96 (20) 19.6 (20) 15.4 (30) 8.6 (23) 5.68 (30) 4.71 (20) 21.10 (25) 2.985 (20) 1.99 (18) 19.7 (20) 3.2 (25) 66.8 (25) 42.6 (25) 12 (21) 1.942 (20) 4.71 (18) 3.158 (20) 3.6 (23) 5.3 (21) 126.8 (25) 5.76 (20) 8.33 (20) 10.98 (20) 7.99 (30) 2.98 (40), 2.69 (100) 29.3 (21) 2.24 (25) 8.428 (20) 2.275 (30) 5.465 (20), 5.42 (25), 4.7 (60) 12.65 (40) 8.22 (25) 4.62 (25)

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Dipole moment, D 1.90 1.89

1.94

1.2 (lq) 0 1.80 (20, B) 1.74 (25, B) 1.8

3.67 (20, B) 2.4 (20, B)

1.17 0 2.93 (20, B) 1.83 (20, lq)

0 1.76 (28, B) 1.2 (20, B) 1.82 (30) 4.08 (25, B) 1.75 (22, B) 1.16 (25, B)

2.85 (25, B) 1.65 (40, lq) 3.33 (20, B) 0 2.56 (25, B) 1.26 (20, B) 1.60

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance 4-Fluoroiodobenzene Fluoromethane 2-Fluoro-2-methylbutane 1-Fluoropentane o-Fluorotoluene m-Fluorotoluene p-Fluorotoluene Formamide Formanilide Formic acid 2-Furaldehyde Furan 2-Furfuryl acetate Furfuryl alcohol Glycerol Glycerol tris(acetate) Glycerol tris(nitrate) Glycerol tris(oleate) Glycerol tris(palmitate) Glycerol tris(sterate) 1,6-Heptadiene Heptacosafluorotributylamine 2,2,3,3,4,4,4-Heptafluoro-1-butanol Heptanal Heptane 1-Heptanethiol Heptanoic acid 1-Heptanol (⫾)-2-Heptanol (⫾)-3-Heptanol 4-Heptanol 2-Heptanone 3-Heptanone 4-Heptanone 1-Heptene Heptylamine Hexachloroacetone Hexachloro-1,3-butadiene Hexadecamethylcyclooctasiloxane Hexadecane 1-Hexadecanol 1,5-Hexadiene 2,4-Hexadiene cis,cis-2,4-Hexadiene trans,trans-2,4-Hexadiene Hexafluoroacetone Hexafluorobenzene 1,1,1,3,3,3-Hexafluoro-2-propanol Hexamethyldisiloxane Hexamethylphosphorotriamide Hexane Hexanedinitrile

Dielectric constant, ⑀ 3.12 (25) 51.0 (⫺142) 5.89 (20) 3.93 (20) 4.23 (25), 4.22 (30), 3.9 (60) 5.41 (25), 4.9 (60) 5.88 (25), 5.86 (30), 5.3 (60) 111.0 (20), 103.5 (40) 58.5 (15), 57.0 (21), 51.1 (25) 42.1 (20), 34.9 (50) 2.88 (4) 5.85 (20) 16.85 (25) 46.5 (20), 42.5 (25) 7.2 (20) 19.25 (20) 3.2 (26) 2.9 (65) 2.8 (70) 2.161 (20) 2.15 (20) 14.4 (25) 9.1 (20) 1.921 (20), 1.85 (70) 4.194 (20) 3.04 (15), 2.6 (71) 11.75 (20) 9.72 (21) 7.07 (23) 6.18 (23) 11.95 (20), 8.27 (100) 12.7 (20) 12.60 (20), 9.46 (80) 2.09 (20) 3.81 (20) 3.93 (19) 2.55 (20) 2.7 (20) 2.046 (30) 3.8 (50) 2.125 (26) 2.207 (25) 2.163 (24) 2.123 (24) 2.104 (⫺71) 2.029 (25) 16.70 (20) 2.2 (20) 31.3 (20) 1.904 (15), 1.890 (20) 32.45 (25)

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Dipole moment, D

1.858 1.92 (25, B) 1.85 (25, B) 1.37 1.82 2.00 3.73 3.37 (25, C) 1.41 3.63 (25, B) 0.66 1.92 (25, lq) 2.68 (25, D) 2.73 (25, B) 3.38 (25, B) 3.11 (23, B) 2.80 (23, B) 2.86 (23, B)

2.26 (40, lq), 2.58 (22, B) 0

1.73 (20, B) 1.73 (20, B) 1.73 (20, B) 1.72 (20, B) 2.61 (22, B) 2.81 (22, B) 2.74 (20, B) 0

0 1.67 (25, B) 0.31 (25, B)

0 0.37 (25, lq) 5.5, 4.31 (25, lq) 0 3.8 (25, B)

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Hexanenitrile 1-Hexanethiol 1,2,6-Hexanetriol Hexanoic acid 1-Hexanol (⫾)-2-Hexanol 3-Hexanol 2-Hexanone 1-Hexene cis-2-Hexene trans-2-Hexene cis-3-Hexene trans-3-Hexene Hexyl acetate Hexylamine 1-Hexyne 2-Hydroxyacetophenone 2-Hydroxybutanoic acid 3-Hydroxybutanoic acid N-(2-Hydroxyethyl)acetamide 4-Hydroxy-4-methyl-2-pentanone 3-Hydroxypropanoic acid Iodobenzene 1-Iodobutane 2-Iodobutane 1-Iodododecane Iodoethane 1-Iodoheptane 3-Iodoheptane 1-Iodohexadecane 1-Iodohexane Iodomethane 1-Iodo-3-methylbutane 2-Iodo-2-methylbutane 1-Iodo-2-methylpropane 2-Iodo-2-methylpropane 1-Iodooctane 2-Iodooctane 1-Iodopentane 3-Iodopentane 1-Iodopropane 2-Iodopropane 3-Iodopropene p-Iodotoluene ␣-Ionone ␤-Ionone Iron pentacarbonyl Isobutanenitrile Isobutene N-Isobutylacetamide Isobutyl acetate Isobutylamine

Dielectric constant, ⑀ 17.26 (25) 4.436 (20) 31.5 (12) 2.600 (25) 13.03 (20), 8.5 (75) 11.06 (25) 9.66 (25) 14.6 (15), 14.56 (20) 2.051 (20) 1.978 (22) 2.069 (23) 1.954 (20) 4.42 (20) 4.08 (20) 2.621 (23) 21.33 (25) 37.7 (23) 31.5 (23) 96.6 (25) 18.2 (25) 30.0 (23) 4.59 (20) 6.27 (20), 4.52 (130) 7.873 (20) 3.9 (20) 10.2 (⫺50), 7.82 (20) 4.92 (22) 6.39 (22) 3.5 (20) 5.37 (20) 6.97 (20) 5.6 (19) 8.19 (20) 6.47 (20) 6.65 (10) 4.6 (25) 5.8 (20) 5.78 (20) 7.432 (20) 7.07 (20) 8.19 (25) 6.1 (19) 4.4 (35) 11 (18) 12 (20) 2.602 (20) 20.4 (24) 2.1225 (15) 111.0 (20) 5.068 (20) 4.43 (21)

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Dipole moment, D

1.13 (25, lq) 1.55 (20, B)

2.68 (22, B) 0 0 0 0 0

0.83

3.24 (20, B) 1.70 2.10 2.12 1.87 (20, C) 1.91 1.86 (22, B) 1.95 (22, B) 1.94 (20, C) 1.62 1.85 (20, B) 2.20 (20, B) 1.89 (20, B) 1.80 (25, lq), 1.90 (20, C) 2.07 (20, C) 1.90 (20, B) 2.03 2.01 (20, B) 1.72 (22, B)

3.61 (25, B) 0.503 1.87 (22, B) 1.27 (25, B)

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Isobutylbenzene Isobutyl butanoate Isobutyl chlorocarbonate Isobutyl formate Isobutyl isocyanate Isobutyl nitrate Isobutyl pentanoate Isobutylsilane Isobutyl trichloroacetate Isobutyl vinyl ether Isobutyronitrile Isopentyl acetate Isopentyl butanoate Isopentyl pentanoate Isopentyl propanoate Isopropyl acetate Isopropylamine Isopropylbenzene Isopropyl carborane N-Isopropylformamide 1-Isopropyl-4-methylbenzene Isopropyl nitrite Isoquinoline Lactic acid Lactonitrile D-Limonene (⫾)-Limonene Maleic anhydride (⫾)-Mandelonitrile D-Mannitol Menthol Methacrylic acid Methacrylonitrile Methane Methanesulfonyl chloride Methanethiol Methanol 2-Methoxyaniline 3-Methoxyaniline 4-Methoxyaniline o-Methoxybenzaldehyde p-Methoxybenzaldehyde Methoxybenzene 2-Methoxyethanol N-(2-Methoxyethyl)acetamide 2-Methoxyethyl acetate 1-Methoxy-2-nitrobenzene o-Methoxyphenol m-Methoxyphenol p-Methoxyphenol 2-Methoxy-4-(2-propenyl)phenol o-Methoxytoluene

Dielectric constant, ⑀ 2.319 (20), 2.298 (30) 4.1 (20) 9.1 (20) 6.41 (20) 11.64 (20) 2.7 (20) 3.8 (19) 2.497 (20) 7.667 (20) 3.34 (20) 20.4 (24) 4.72 (20), 4.63 (30) 4.0 (20) 3.6 (19) 4.2 (20) 5.627 (20) 2.38 (20) 45.0 (20) 65.7 (25) 2.24 (20) 13.92 (⫺13) 11.0 (25) 22 (17) 38 (20) 2.4 (20), 2.37 (25) 2.3 (20) 52.75 (53) 17.8 (23) 24.6 (170)

1.676 (⫺182), 1.000 94 (0) 34.0 (20) 41.8 (⫺20), 33.0 (20) 5.230 (30) 8.76 (25) 7.85 (60) 22.3 (22), 22.0 (30), 10.4 (248) 4.30 (21), 3.9 (70) 17.2 (25), 16.0 (30) 80.7 (25) 8.25 (20) 45.75 (20) 11.95 (25) 11.59 (25) 11.05 (60)

Dipole moment, D 0.31 (20, lq) 1.9 1.89 (20, B)

3.61 (25, B) 1.84 (22, B), 1.76 (30, lq) 1.8 (28, B) 1.86 (22, B) 1.19 0.79

0 2.73

1.57 (25, B) 0.63 (25, B)

1.55 (20, B) 1.65 3.69 0 1.52 (g) 1.70

4.34 (20, B) 3.26 (35, B) 1.38 2.36 2.13 (30, B) 4.83

2.46 (25, B) 3.5 (20)

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance m-Methoxytoluene p-Methoxytoluene Methoxytrimethylsilane N-Methylacetamide Methyl acetate Methyl acrylate Methylamine Methyl 2-aminobenzoate N-Methylaniline 2-Methylaniline 3-Methylaniline 4-Methylaniline N-Methylbenzenesulfonamide Methyl benzoate 2-Methyl-1,2-butadiene 2-Methyl-1,3-butadiene 2-Methylbutane 2-Methyl-2-butanethiol Methyl butanoate 3-Methylbutanoic acid 2-Methyl-1-butanol 2-Methyl-2-butanol 3-Methyl-1-butanol 3-Methyl-2-butanol 3-Methyl-2-butanone 2-Methyl-1-butene 2-Methyl-2-butene 3-Methyl-1-butene 2-Methyl-1-butene-2-one 2-Methylbutyl acetate 3-Methylbutyl 3-methylbutanoate 3-Methylbutyronitrile Methyl carbamate Methyl chloroacetate N-Methyl-2-chloroacetamide Methyl 4-chlorobutanoate Methyl crotonate Methyl cyanoacetate Methylcyclohexane 2-Methylcyclohexanol cis-3-Methylcyclohexanol trans-3-Methylcyclohexanol 4-Methylcyclohexanol 2-Methylcyclohexanone 3-Methylcyclohexanone 4-Methylcyclohexanone Methylcyclopentane 1-Methylcyclopentanol Methyl decanoate Methyl dodecanoate N-Methylformamide Methyl formate

Dielectric constant, ⑀ 3.5 (20) 4.0 (20) 3.248 (25) 178.9 (30), 138.6 (60) 7.07 (15), 7.03 (20), 6.68 (25) 7.03 (30) 16.7 (⫺58), 11.4 (⫺10), 10.0 (18) 21.9 (25) 5.96 (20) 6.138 (25) 5.816 (25) 5.058 (25) 67.1 (30) 6.64 (30) 2.1 (25) 2.098 (20) 1.871 (0), 1.845 (20) 5.083 (20) 5.6 (20), 5.48 (29) 2.64 (20) 15.63 (25) 5.78 (25) 15.63 (20), 14.7 (25), 5.82 (130) 12.1 (25) 10.37 (20) 2.180 (20) 1.979 (23) 1.0028 (100, g) 10.39 (30) 4.63 (30) 4.39 (15) 18 (220) 18.48 (55) 12.0 (20) 92.3 (50) 9.51 (30) 6.664 (20) 29.3 (20), 19.23 (50), 17.57 (65) 2.024 (20) 16.05 (20) 8.05 (20) 16 (⫺15), 14.0 (20) 18 (⫺80), 12.4 (20) 15 (⫺41), 12.35 (20) 1.985 (20) 7.11 (37)

200.1 (15), 189.0 (20), 182.4 (25) 9.20 (15), 8.5 (20)

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Dipole moment, D

4.39 (20, D) 1.72 1.77 (25, B) 1.31 1.67 (25, B)

1.86 (25, B) 0.15 0.25 0.13 1.72 (22, B) 0.63 (25) 1.9 1.72 (20, B) 1.82 (25, B)

0.52 (20, lq) 0.11 (25, lq), 0.34 (25, B) 0.320 1.82 (22) 3.62 (25, C)

0 1.95 (25, B) 1.91 1.75 1.9 (25, B) 2.98 (25, B) 3.06 (25, B) 3.07 (25, B) 0 1.65 (20, Hx) 1.70 (20, Hx) 3.83 1.77

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance 2-Methylfuran Methyl furan-2-carboxylate (mono)Methyl glutarate 2-Methylheptane 2-Methyl-2-heptanol 2-Methyl-3-heptanol 2-Methyl-4-heptanol 3-Methyl-3-heptanol 3-Methyl-4-heptanol 4-Methyl-3-heptanol 4-Methyl-4-heptanol 2-Methylhexane 3-Methylhexane Methyl hexanoate 2-Methyl-2-hexanol 3-Methyl-2-hexanol 3-Methyl-3-hexanol 5-Methyl-2-hexanone Methyl isobutanoate Methylisocyanate Methyl methacrylate N-Methyl methanesulfonamide Methyl o-methoxybenzene Methyl p-methoxybenzoate N-Methyl-2-methylbutanamide N-Methyl-3-methylbutanamide Methyl 3-(methylthio)propanoate 1-Methylnaphthalene Methyl nitrate Methyl nitrite Methyl o-nitrobenzoate 2-Methyloctane 3-Methyloctane 4-Methyloctane Methyl oleate 2-Methyl-1,3-pentadiene 3-Methyl-1,3-pentadiene 4-Methyl-1,3-pentadiene N-Methylpentanamide 2-Methylpentane 3-Methylpentane 2-Methyl-2,4-pentanediol 4-Methylpentanenitrile Methyl pentanoate 3-Methyl-1-pentanol 3-Methyl-3-pentanol 4-Methyl-2-pentanone 4-Methylpentenenitrile 4-Methyl-3-penten-2-one 1-Methyl-1-phenylhydrazine Methyl phenyl sulfide Methyl phenyl sulfone

Dielectric constant, ⑀ 2.76 (20) 11.01 (20) 8.37 (20) 1.95 (20) 3.38 (⫺7), 2.46 (25) 3.37 (20), 3.75 (60) 3.30 (20), 3.65 (60) 3.74 (20), 2.89 (60) 9.1 (⫺20), 7.4 (20) 5.25 (20), 4.62 (55) 2.87 (20), 3.27 (60) 1.922 (20) 1.920 (20) 4.615 (20) 3.257 (24) 4.990 (24) 3.248 (25) 13.53 (20) 21.75 (16) 6.32 (30) 104.4 (25) 7.7 (21) 4.3 (33) 123.0 (34) 114.0 (26) 8.66 (30) 2.92 (20) 23.9 (20) 20.77 (⫺73) 28 (25) 1.97 (20) 1.97 (20) 3.211 (20) 2.422 (25) 2.426 (25) 2.599 (20) 131.0 (13) 1.886 (20) 1.886 (20) 23.4 (20) 17.5 (22) 4.992 (20) 15.2 (25) 4.322 (20) 15.6 (0), 15.1 (20), 11.78 (40) 17.5 (22) 15.6 (0) 7.3 (19) 37.9 (100)

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Dipole moment, D 0.65

0 1.63 (20, B)

0 0 1.70 (20, Hx)

1.98 (20, B) 2.8 1.68 (25, B)

0

3.67 (30, B) 0 0 0

0 0 2.9 3.53 (25, B) 1.62 (22, B)

3.5 2.8 1.84 (15, B) 1.38 (20, B)

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance 2-Methylpropanal N-Methylpropanamide 2-Methyl-1-propanamine 2-Methylpropane 2-Methylpropanenitrile 2-Methyl-1-propanethiol 2-Methyl-2-propanethiol Methyl propanoate 2-Methylpropanoic acid 2-Methylpropanoic anhydride 2-Methyl-1-propanol 2-Methyl-2-propanol 2-Methylpropene 2-Methyl-2-propenenitrile 2-Methylpropenoic acid 2-Methylpropyl acetate 2-Methyl-1-propylamine (2-Methylpropyl)benzene 2-Methylpropyl formate 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 2-Methylpyridine-1-oxide 3-Methylpyridine-1-oxide N-Methylpyrrolidine N-Methyl-2-pyrrolidinone Methyl salicylate 3-Methyl sulfolane Methyl tetradecanoate 2-Methyltetrahydrofuran Methyl tetrahydrothiophene-2carboxylate Methyl thiocyanate 2-Methylthiophene 3-Methylthiophene Methyl thiophene-2-carboxylate Methyl trifluoromethyl sulfone Morpholine ␤-Myrcene Naphthalene 1-Naphthonitrile 2-Naphthonitrile o-Nitroaniline m-Nitroaniline p-Nitroaniline o-Nitroanisole m-Nitroanisole p-Nitroanisole Nitrobenzene m-Nitrobenzyl alcohol 2-Nitrobiphenyl Nitroethane

Dielectric constant, ⑀

170.0 (20), 151 (40) 4.43 (21) 1.752 (25) 24.42 (20) 4.961 (25) 5.475 (20) 6.200 (20) 2.58 (20) 13.6 (19) 26 (⫺34), 17.93 (20) 12.47 (25), 10.9 (30), 8.49 (50)

5.07 (20) 4.43 (21) 2.32 (20) 6.41 (20) 10.18 (20) 11.10 (30) 12.2 (20) 36.4 (50) 28.26 (45) 32.2 (25) 32.55 (20), 32.2 (25) 9.41 (30), 8.80 (41) 29.4 (25)

top of rh base of rh cap height base of text

Dipole moment, D 2.6 3.59 1.3 0.132 4.29 1.66 1.70 (22, B) 1.08 (25, lq) 1.64 1.67 (22, B) 0.50 3.69 1.6 1.87 (22, B) 1.27 (27) 0 1.88 (22) 1.85 2.41 (25, B) 2.70

4.09 (30, B) 2.47 (25, B) 1.62 (25, B)

6.97 (25) 7.30 (20) 4.3 (19)

8.81 (20) 32.0 (20) 7.42 (25) 2.3 (25) 2.54 (90) 16 (70) 17 (70) 47.3 (80), 34.5 (90) 35.6 (125) 78.5 (155), 56.3 (160) 45.75 (20) 25.7 (45) 26.95 (65) 35.6 (20), 34.82 (25), 24.9 (90) 22 (20) 29.11 (15), 28.06 (30), 27.4 (35)

3.34 (20, B) 0.674 0.95

1.55 0

4.28 (20, B) 6.3 (25, B) 4.83

4.22 3.83 (20, B) 3.23

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance 2-Nitro-ethylbenzene Nitromethane 1-Nitro-2-methoxybenzene o-Nitrophenol m-Nitrophenol p-Nitrophenol 1-Nitropropane 2-Nitropropane N-Nitrosodimethylamine o-Nitrotoluene m-Nitrotoluene p-Nitrotoluene Nonane Nonanoic acid 1-Nonanol 1-Nonene (trans, trans)-9,12-Octadecadienoic acid Octamethylcyclotetrasiloxane Octamethyltrisiloxane Octane Octanenitrile Octanoic acid 1-Octanol 2-Octanol 2-Octanone 1-Octene cis-2-Octene trans-2-Octene Oleic acid Oxalyl chloride Palmitic acid Paraldehyde Parathion Pentachloroethane 2,3,4,5,6-Pentachlorotoluene Pentadecane cis-1,3-Pentadiene 1,4-Pentadiene Pentanal Pentane 1,2-Pentanediol 1,4-Pentanediol 1,5-Pentanediol 2,3-Pentanediol 2,4-Pentanediol 2,4-Pentanedione Pentanenitrile 1-Pentanethiol Pentanoic acid 1-Pentanol 2-Pentanol

Dielectric constant, ⑀ 21.9 (0) 37.27 (20), 35.87 (30), 35.1 (35) 16.50 (50) 35.45 (100) 42.20 (120) 24.70 (15), 23.24 (30), 22.7 (35) 26.74 (15), 25.52 (30) 53 (20) 26.36 (20), 22.0 (58) 24.95 (30), 22 (58) 22.2 (58) 1.972 (20), 1.85 (110) 2.48 (22) 2.18 (20) 2.70 (70), 2.60 (120) 2.4 (20) 2.3 (20) 1.948 (20), 1.83 (110) 13.90 (20) 2.85 (15), 2.45 (20) 11.3 (10), 10.30 (20) 8.13 (20), 6.52 (40) 9.51 (20), 7.42 (100) 2.113 (20) 2.06 (25) 2.00 (25) 2.34 (20) 3.470 (21) 2.3 (70) 13.9 (25) 3.73 (20), 3.716 (25) 4.8 (20) 2.32 (25) 2.054 (24) 10.1 (17), 10.00 (20) 2.011 (⫺90), 1.837 (20) 17.31 (24) 26.74 (23) 26.2 (20) 17.37 (24) 24.69 (21) 26.52 (30) 20.04 (20) 4.85 (20), 4.55 (25), 4.23 (50) 2.66 (21) 16.9 (20), 15.13 (25) 13.71 (25)

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Dipole moment, D

3.46 4.83 3.14 (25, B)

3.66 3.73 4.01 (20, B) 3.72 (20, B) 4.20 (20, B) 4.47 (25, B) 0 0.8 1.72 (20, B) 0 1.40 (18, Hx) 0.42 (25, lq), 0.67 (25, B) 0.64 (25, lq) 0 1.15 (25, lq) 1.72 (20, B) 1.65 (20, B) 2.72 (15, B) 0 0 0 1.2 0.93 (20, B) 1.43 4.98 (25, B) 0.92 0 0.50 (25, B) 2.59 (20, B) 0

2.45 (20, D)

3.03 4.12, 3.57 (25, B) 1.54 (25, lq) 1.61 (20, D) 1.71 (20, B) 1.66 (22, B)

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance 3-Pentanol 2-Pentanone 3-Pentanone 2-Pentanone oxime 1-Pentene cis-2-Pentene trans-2-Pentene Pentyl acetate Pentylamine Pentyl formate Pentyl nitrate Pentyl nitrite tert-Pentyl nitrite Phenanthrene Phenol Phenoxyacetylene Phenyl acetate Phenylacetic acid Phenylacetonitrile Phenylacetylene 1-Phenylethanol 2-Phenylethanol Phenylhydrazine Phenyl isocyanate Phenyl isothiocyanate 1-Phenylpropene 2-Phenylpropene 3-Phenylpropene Phenyl salicylate Phosgene Phthalide (⫾)-␣-Pinene L-␤-Pinene Piperidine Propanal Propane 1,2-Propanediamine 1,3-Propanediamine 1,2-Propanediol 1,3-Propanediol 1,2-Propanediol dinitrate 1,3-Propanediol dinitrate 1,2-Propanedithiol 1,3-Propanedithiol Propanenitrile 1-Propanethiol 2-Propanethiol 1,2,3-Propanetriol 1-acetate Propanoic acid Propanoic anhydride 1-Propanol 2-Propanol

Dielectric constant, ⑀ 13.35 (25) 15.45 (20), 11.73 (80) 19.4 (⫺20), 17.00 (20) 3.3 (25) 2.011 (20)

4.79 (20) 4.27 (20) 5.7 (19) 9.0 (18) 7.21 (25) 10.88 (25) 2.8 (20) 12.40 (30), 9.78 (60) 4.76 (25) 5.40 (25) 3.47 (80) 17.87 (26), 8.5 (234) 2.98 (20) 8.77 (20), 7.6 (90) 12.31 (20) 7.15 (20) 8.94 (20) 10 (20) 2.7 (20) 2.3 (20) 2.6 (20) 6.3 (50) 4.7 (0), 4.3 (22) 36 (75) 2.64 (25), 2.26 (30) 2.76 (20) 4.33 (20) 18.5 (17) 1.668 (20) 10.2 9.55 32.0 (20), 27.5 (30) 35.1 (20) 26.80 (20) 18.97 (20) 7.24 (20) 8.11 (30) 29.7 (20) 5.94 (15), 1.55 (25) 5.95 (25) 38.57 (⫺31), 7.11 (20) 3.30 (10), 3.44 (25) 18.30 (20) 20.8 (20), 20.33 (25) 20.18 (20), 18.3 (25), 16.2 (40)

top of rh base of rh cap height base of text

Dipole moment, D 1.64 (22, B) 2.72 (22, B) 2.72 (20, B) 0.5 0 0 1.75 1.55 (30, B) 1.90

0 1.224 1.42 (25, lq) 1.54 (22, B) 3.47 (27, B) 0.72 (20, B) 1.51 (20, B) 1.67 (25, B)

0.60 (25, B) 1.19 (25, B) 2.52 0.084 1.96 (25, B) 2.27 (25, D) 2.52 (25, D)

4.05 1.68 1.61 1.76 1.55 1.58

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance 2-Propenal Propene Propenenitrile 2-Propen-1-ol Propionaldehyde (propanal) Propionamide Propyl acetate N-Propylacetamide Propylamine Propylbenzene tPropyl benzoate Propyl butanoate Propyl carbamate Propylene carbonate Propyleneimine 1,2-Propylene oxide Propyl formate Propyl nitrate Propyl nitrite Propyl pentanoate N-Propylpropanamide Propyl propanoate Propyl trichloroacetate Propyne 2-Propyn-1-ol Pulegone Pyridazine Pyrazine Pyridine Pyridine-1-oxide Pyrimidine 1H-Pyrrole Pyrrolidine 2-Pyrrolidone Quinoline Safrole Salicylaldehyde D-Sorbitol Squalane Squalene Stearic acid Styrene Succinonitrile ␣-Terpinene Terpinolene 1,1,2,2-Tetrabromoethane 1,1,2,2-Tetrachlorodifluoroethane 1,1,1,2-Tetrachloroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene 1,1,3,4-Tetrachlorohexafluorobutane

Dielectric constant, ⑀

2.137 (⫺53), 1.88 (20), 1.44 (90) 33.0 (20) 21.6 (15), 19.7 (20) 18.5 (17) 5.62 (20) 117.8 (25) 5.31 (20), 5.08 (26) 2.37 (20), 2.351 (30) 5.78 (30) 4.3 (20) 12.06 (65) 66.14 (20)

7.72 (19), 6.92 (30) 14 (18) 12.35 (⫺23) 4 (19) 118.1 (25) 5.25 (20) 8.32 (25) 3.218 (⫺27) 20.8 (20) 9.5 (20) 2.80 (50) 13.26 (20), 12.3 (25), 9.4 (116) 35.94 (70) 8.00 (20), 8.13 (25) 8.30 (20) 9.16 (20), 9.00 (25) 3.1 (21) 18.35 (20) 35.5 (80) 1.911 (100) 2.29 (70), 2.26 (100) 2.47 (20), 2.43 (25), 2.32 (75) 62.6 (25), 56.5 (57), 54 (68) 2.45 (25) 2.29 (25) 8.6 (3), 7.0 (22), 6.72 (30) 2.52 (35) 9.22 (⫺66) 8.50 (20) 2.30 (25), 2.268 (30) 2.86 (20)

cap height base of text

Dipole moment, D 3.12 0.366 3.87 1.60 2.75 3.4 (30, B) 1.86 (25, B) 1.17 0

4.9 1.77 (cis), 1.60 (trans) 2.00 1.91 (22, B) 3.01 (20, B)

1.79 (22, B) 0.784 1.13 2.00 (25, B) 4.22 0 2.215 2.33 1.74 1.58 (20, B) 3.55 (25, B) 2.29 2.86 (20, B) 0 0.68 (25, B) 1.76 (25, D) 0.13 (25, lq) 3.68 (30, toluene)

1.41

1.32 0

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Tetradecafluorohexane Tetradecamethylhexasiloxane Tetradecane Tetradecanoic acid 1-Tetradecanol Tetraethylene glycol Tetraethyl lead Tetraethylsilane Tetraethyl silicate Tetrafluoromethane 2,2,3,3-Tetrafluoro-1-propanol Tetrahydrofuran Tetrahydro-2-furanmethanol 2-Tetrahydrofurfuryl acetate 1,2,3,4-Tetrahydronaphthalene 1,2,3,4-Tetrahydro-2-naphthol Tetrahydropyran Tetrahydrothiophene Tetrahydrothiophene-1,1-dioxide (sulfolane) Tetrahydrothiophene-S-oxide Tetrakis(methylthio)methane Tetramethoxymethane Tetramethyl germanium 1,1,3,3-Tetramethylguanidine Tetramethylsilane Tetramethyl silicate 1,1,2,2-Tetramethylurea Tetranitromethane Tetrathiomethylmethane Thiacyclopentane Thioacetic acid Thiophene Thymol Toluene o-Toluidine m-Toluidine p-Toluidine m-Tolunitrile p-Tolunitrile Tribenzylamine 2,2,2-Tribromoacetaldehyde Tribromochloromethane Tribromofluoromethane Tribromomethane Tribromonitromethane 1,2,3-Tribromopropane Tributylamine Tributyl borate Tributyl phosphate Tributyl phosphite Trichloroacetaldehyde

Dielectric constant, ⑀ 1.76 (25) 2.5 (20)

4.72 (38), 4.40 (48) 20.44 (20) 2.09 (20) 4.1 (20) 1.685 (⫺147) 21.03 (25) 11.6 (⫺70), 7.52 (22) 13.61 (23), 13.48 (30) 9.65 (20) 2.77 (25) 11.7 (20), 6.7 (90) 5.66 (20), 5.61 (25) 43.26 (30) 42.96 (25), 42.5 (30) 2.818 (70) 2.40 (20) 1.817 (24) 11.5 (25) 1.921 (20) 6.0 (20) 23.10 (20) 2.317 (25) 2.82 (70)

top of rh base of rh cap height base of text

Dipole moment, D

1.58 (20, lq) 0 0.76 (25, B) 1.69 (25, C) 5.84 (20, lq) 0.3 (20, B) 0 1.72 (32, B)

1.75 (25, B) 2.12 (35, lq) 0 1.74 1.9 4.81 (25, B)

0 3.47 (25, B) 0 1.90 (25, B)

14.30 (25) 2.74 (20), 2.57 (25) 2.385 (20), 2.364 (30) 6.34 (18), 6.14 (25), 5.71 (58) 5.95 (18), 5.82 (25), 5.45 (58) 5.06 (60)

7.6 (20) 2.60 (60) 3.00 (20) 4.404 (10), 4.39 (20) 9.03 (25) 6.45 (20), 6.00 (30) 2.34 (20) 2.23 (20) 8.34 (20), 7.96 (30) 7.6 (⫺40), 6.9 (20), 6.8 (25)

0.55 1.55 (25, B) 0.375 1.60 (25, B) 1.45 (25, B) 1.52 (25, B) 4.21 (22, B) 4.47 (20, B) 0.65 (20, B) 1.70 (20, C)

0.99 1.59 (25, B) 0.78 (25, B) 0.78 (25, C) 3.07 (25, B) 1.92 (20, C) 1.96 (25, B)

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance Trichloroacetic acid Trichloroacetic anhydride Trichloroacetonitrile 4,4,4-Trichlorobutanal 1,2,2-Trichloro-1,1-difluoroethane 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene Trichloroethylsilane Trichlorofluoromethane (Trichloromethyl)benzene Trichloromethylsilane Trichloronitromethane 2,4,6-Trichlorophenol 1,2,3-Trichloropropane Trichlorosilane ␣,␣,␣-Trichlorotoluene 1,1,2-Trichloro-1,2,2-trifluoroethane Tridecane 1-Tridecene Triethanolamine Triethoxymethane Triethylaluminum Triethylamine Triethylborane Triethylene glycol Triethylenetetramine Triethyl orthovanadate Triethyl phosphate Triethylphosphine oxide Triethylphosphine sulfide Triethyl phosphite Trifluoroacetic acid Trifluoroacetic anhydride 1,1,1-Trifluoroethane 2,2,2-Trifluoroethanol Trifluoromethane (Trifluoromethyl)benzene 1-Trifluoromethyl-3-nitrobenzene ␣,␣,␣-Trifluorotoluene Trimethoxymethylsilane Trimethylamine 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Trimethyl borate 2,2,3-Trimethylbutane Trimethylchlorosilane Trimethylene sulfide 2,2,5-Trimethylhexane 2,3,5-Trimethylhexane 2,2,3-Trimethylpentane

Dielectric constant, ⑀ 4.34 (60) 5.0 (25) 7.85 (19) 10.0 (18) 4.01 (30) 7.1 (7), 7.24 (20) 7.19 (25) 3.42 (16), 3.39 (28) 3.00 (25), 2.28 (29) 6.9 (21)

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Dipole moment, D 1.1 (25, B, dimer) 1.93 (19, lq)

1.755 1.45 0.77 (30, lq), 0.95 (30, B) 2.0 0.45 2.0 1.87 (25, B)

7.32 (25) 7.5 (20) 6.9 (21) 2.41 (25) 2.02 (20) 2.14 (20) 29.36 (25) 4.779 (20) 2.9 (20) 2.418 (20) 1.874 (20) 23.69 (20) 10.76 (20) 3.333 (25) 13.43 (15), 13.20 (25), 10.93 (65) 35.5 (50) 39.0 (98) 5.0 8.42 (20), 5.76 (50) 2.7 (25) 27.68 (20) 5.2 (26) 9.22 (25) 17.0 (30) 9.2 (30), 8.1 (60) 4.9 (25) 2.44 (25) 2.66 (20), 2.609 (30) 2.38 (20), 2.36 (30) 2.28 (20) 2.276 (20) 1.930 (20) 10.21 (0)

1.962 (20)

1.88 (25, D) 1.61 0.86 2.17 (20, B) 0 0 3.57 (25, B)

0.66 5.58 (20, lq)

3.08 (25, B)

1.82 (25, D) 2.28 2.347 2.03 (25, cHex) 1.651 2.86

0.612 0 0 0 0.82 (25, C) 0 1.85 0 0 0

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TABLE 5.17 Dielectric Constant (Permittivity) and Dipole Moment of Various Organic Substances (Continued) Substance 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane 2,3,4-Trimethylpentane Trimethyl phosphate Trimethylphosphine sulfide Trimethyl phosphite 2,4,6-Trimethylpyridine 2,4,6-Trinitrophenol 1,3,5-Trioxane Triphenyl phosphite Tris(4-ethylphenyl) phosphite Tris(2-methylphenyl) phosphate Tris(3-methylphenyl) phosphate Tris(4-methylphenyl) phosphate Tris(m-tolyl) phosphite Tris(p-tolyl) phosphite Tri-o-tolyl phosphate Undecane 2-Undecanone 1-Undecene Urea Vinyl acetate Vinyl chloride Vinyl isocyanate 2-Vinylpyridine 4-Vinylpyridine o-Xylene m-Xylene p-Xylene Xylitol

Dielectric constant, ⑀ 1.940 (20) 1.98 (20) 1.97 (20) 20.6 (20)

7.807 (25) 4.0 (21) 15.55 (65) 3.67 (45), 3.57 (65) 3.74 (15), 3.61 (45) 6.7 (25)

3.67 (15), 3.53 (45) 3.88 (15), 3.74 (45) 6.92 (40) 2.00 (20), 1.84 (150) 2.14 (20)

6.26 (17) 10.62 (25) 9.126 (20) 10.50 (20) 2.562 (20), 2.54 (30) 2.359 (20), 2.35 (30) 2.273 (20), 2.22 (50) 40.0 (20)

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Dipole moment, D 0 0 0 3.2 71.6 (20) 1.83 (20, C) 1.95 (25, B) 2.08 2.04 (25, B) 2.08 (25, B) 2.9 3.0 3.2 1.62 (25, B) 1.77 (25, B) 2.84 (40, C) 0 2.71 (15, B) 0 4.59 (25, D) 1.79 (25, B) 1.45

0.62 0.33 (20, lq), 0.37 (20, B) 0

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TABLE 5.18 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances

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For the majority of compounds the dependence of the surface tension ␥ on the temperature can be given as:

␥ ⫽ a ⫺ bt where a and b are constants and t is the temperature in degrees Celsius. The values of the dipole moment are for the gas phase. Surface tension, mN · m⫺1 Substance Air AlBr3 Ar (g)

Viscosity, mN · s · m⫺2 0.018220, 0.0231127

0.023320, 0.0288127

B2H6 (diborane) B4H10 B5H9 B6H10 B3H6N3 Br2 (g) (lq) BrF3 BrF5 Cl2 (g) (lq) ClF3 ClF5 ClO3F CO (g) (lq) CO2 (g) (lq) COCl2 COF2 COS COSe CS

0.017127, 0.0217127 1.872⫺92.5 21.125

0.4812

0.017520, 0.0221127 0.014720, 0.0197127 0.07120

a

b

0

34.28

0.2493

1.61 1.59 0.20 0 0 0

54.41 41.67

0.1043 0.097 81

31.90

0.1280

⫺2.92

0.2030

⫺3.13

0.1783

0

45.5

0.1820

1.1 1.51 0

38.30 25.24

0.0999 0.1098

19.87

0.1897

0.554

26.9

0.1660

0.023 0.112

12.24

0.1576

⫺30.20

0.2073

5.2

1.000 517 2 1.538⫺191, 1.325⫺132 8.8335 12.620 2.40⫺72, 2.0520 2.580

1.2520, 1.0316, 0.74425 2.2220 0.6224 0.013220

Dipole moment, D

1.000 536 4 3.38100

(lq) AsBr3 AsCl3 AsH3 (arsine) BBr3 BCl3 BF3

Dielectric constant, ⑀

1.012820 3.148425 106.825 7.9124.5 2.147⫺65, 1.9114 4.39420, 4.2925 4.28⫺80 2.194⫺123 1.000 700

1.000 922 1.600⬚C, 50 atm, 1.44923 4.3422 4.47⫺88 3.4710

0 0.486 2.13 2.50 0

0 6.14⫺10 1.17 0.95 0.712 0.73 1.98

2.6710

22.59

0.1456

12.12

0.1779

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TABLE 5.18 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances (Continued)

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Surface tension, mN · m⫺1 Substance CS2 (g) (lq) CrO2Cl2 D2 (deuterium) DH D2O

Viscosity, mN · s · m⫺2

0.4290, 0.37520, 0.35225 0.012627, 0.0154127 0.011125 (g), 1.09825 (lq)

F2 GaCl3 GeBr4 GeBr4 GeCl4 GeClH3 H2 (g) t (lq) HBr (g) (lq) He (g) (lq) (II) (III) (IV) HCl (g) (lq) HClO HCN HCNO (isocyanate) HCNS HF HFO HI (g) (lq) HN3 (azide) H2O (see Table 5.19) H2O2 HNO3 H2S (g) (lq) H2Se

Dielectric constant, ⑀

Dipole moment, D

1.00290 2.63220

0

2.620 1.290⫺255, 1.277⫺253 1.26916.78 K 79.7520, 78.2525 1.491⫺220, 1.54⫺202

0.47

1.87

0.008820, 0.109127

0.83⫺67 0.019627, 0.024427

1.000 253 8 1.27913.5 K, 1.22820.4 K 1.003 130 8.23⫺86, 3.8225 1.000 065 0

0 2.13 0

1.00460

0.2350, 0.20618, 0.18325

114.920

35.29

0.1484

6.537 71.7220

35.0 35.5130 35.5130 22.4430

2.80⫺258

0.1883 68.3840 0.1646 0.1000 33.7050 33.7050

2.12⫺254

0.827 13.10

0.2079

0

1.05552.055 K

0.014627, 0.0197127 0.51⫺95

b

⫺16.10 0.85

2.95526 2.4630, 2.43025

a

0.3510.50 K 0.1513.61 K 0.3720.50 K

0.3172.00 K 0.1311.13 K 0.3541.40 K

1.109

14.3⫺114, 4.6028 1.3 2.98

19.4510

18.3320

1.6

0.2560

83.60 1.002 340 3.87⫺53, 2.9022

1.7 1.826 2.23 0.448

10.41

0.078 67

78.97

0.1549

48.95 22.32

0.1758 0.1482

1.70

1.2520

84.20, 74.617

0.4120

1.00400 5.9310

1.573 2.17 0.97 0.24

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TABLE 5.18 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances (Continued)

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Surface tension, mN · m⫺1 Substance HSO3Cl HSO3F H2SO4 H2Te Hg I2 IBr IF IF5 IF7 IOF5 Kr (g) (lq) Mn2O7 Ne (g) (lq) N2 (g)

Viscosity, mN · s · m⫺2 2.4320 1.5625 24.5425 1.55220, 1.52625, 1.40250 1.98116

N2H4 (hydrazine) Ni(CO)4 NO N2O (g) (lq) NO2 N2O4 N2O3 NOBr NOCl NO2Cl NOF NO2F NO3 O2 (g) (lq) O3

⬍0.2 0 11.1118

0.017620, 0.0222127

0.254⫺33.5 0.9720, 0.87625, 0.62850 0.019227, 0.0238127 0.014620, 0.0194127

0 0.726 1.95 2.18

1.644⫺153.4 3.2820 1.000 063 920

0

1.1907⫺247.1 1.000 548 020

0

1.468⫺210, 1.454⫺203 1.00720 22.4⫺33.5, 16.6120 52.920, 51.725

b

29.03 490.6

0.2619 0.2049

33.16

0.1318

40.576 (in K)

0.2890 (in K)

26.42 (in K)

0.2265 (in K)

1.471 37.91⫺50 1.75

0.159 1.001 130

2.5625, 2.4420 13.415 18.212

31.13⫺70 1.000 494 720 1.568⫺218.7, 1.507⫺193 4.75⫺183

35.38⫺40

72.41

0.2407

18.11 ⫺67.48

0.1117 0.5853

5.09

0.2032

29.49

0.1493

14.00 8.26

0.1165 0.1854

⫺33.72

0.2561

0.161

1.5215 0.5320, 0.40225

0.020420, 0.0261127

a

⬍0.05

0.025020, 0.0331127

0.030320, 0.0389127

Dipole moment, D

6060 ca. 12025 10025

37.1320 1.9723 1.7525

(lq) NH3 (g) (lq)

Dielectric constant, ⑀

0.316 0.5 2.122 1.8 1.9 0.53 1.73 0.47 0

0.534

38.1⫺183

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TABLE 5.18 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances (Continued)

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Surface tension, mN · m⫺1 Substance OF2 O2F2 (FOOF) OsO4 P (lq) PBr3 PCl3 PCl5 PCl2F3 PCl3F2 PCl4F PF3 PF5 PH3 PI3 PO3 POCl3 POF3 PSCl3 PSF3 PbCl4 ReO2Cl3 ReO3Cl S SCl2 S2Cl2 dimer S2F2 FSSF isomer S⫽SF2 isomer SF4 SF6 S2F10 SO2 (g) (lq) SO3 SOBr2 SOCl2 SOF2 SO2Cl2 SO2F2 SbCl3 SbCl5 SbF5 SbH3 Se (lq) SeF4

Viscosity, mN · s · m⫺2

Dielectric constant, ⑀

Dipole moment, D

a

b

45.34 31.14

0.1283 0.1266

61.66 40.44 35.22

0.067 71 0.1158 0.1275

37.00

0.1272

57.00 54.05

0.2485 0.1979

0.297 1.44 0

0.6620, 0.52925, 0.43950

4.09634 3.920 3.4325, 3.5017 2.85160, 2.7165 2.813⫺45 2.375⫺5 2.650.5

2.915 4.1265 1.06525

13.725 5.822

0.56 0.78 0.9

1.03 0 0.574 0 2.54 1.868 1.42 0.64

2.7820

0.015327, 0.0198127 0.012927, 0.0175127

3.499134 2.91525 4.7915

0.36 1.0

46.23

0.1464

1.81⫺50

1.45 1.03 0.632 0

12.87 5.66

0.1734 0.1190

2.02020 1.00930

0 1.63 26.58

0.1948

46.28 36.10

0.0750 0.1416

32.10

0.1328

47.87

0.1238

49.07

0.1937

38.61

0.1274

16.325 3.1118 9.0620 9.2520, 8.67525 9.1520 33.275 3.2220

0 9.11 1.45 1.63 1.81 1.12 3.93 0 0.12

5.44237.5 1.78

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TABLE 5.18 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances (Continued)

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Surface tension, mN · m⫺1 Substance SeF6 SeOCl2 SeO2 SiCl4 SiF4 SiH4 SiHCl3 SiH3Cl SnBr4 SnCl4 TeF6 TiCl4 UF6 (g) (lq) VCl4 VOBr3 VOCl3 Xe (g)

Viscosity, mN · s · m⫺2

Dielectric constant, ⑀ 46.220

99.425, 96.250

2.2480

0.4150, 0.32625 3.16930 3.0140, 2.8920

0.022820, 0.030127

2.84314, 2.8020 1.002 9267 2.1865 3.0525 3.625 3.425 1.001 23 1.880⫺111.9 4.10125

(lq, II) XeF6

Dipole moment, D 0 2.64 2.62 0 0 0 0.86 1.31 0 0 0 0 0

a

b

20.78

0.099 62

20.43

0.1076

29.92

0.1134

33.5420 25.5

31.0640 0.1240

0 0.3 0

36.3620

0.3451.00 K

33.6040

0.3172.00 K

TABLE 5.19 Refractive Index, Viscosity, Dielectric Constant, and Surface Tension of Water at Various Temperatures

Temp., ⬚C

Refractive index, nD

Viscosity, mN · s · m⫺2

Dielectric constant, ⑀

Surface tension, mN · s · m⫺2

0 5 10 15 20 25 30 35 40 50 60 70 80 90 100

1.333 95 1.333 88 1.333 69 1.333 39 1.333 00 1.332 50 1.331 94 1.331 31 1.330 61 1.329 04 1.327 25 1.325 11

1.793 1.521 1.307 1.135 1.002 0.890 3 0.797 7 0.719 0 0.653 2 0.547 0 0.466 5 0.404 0 0.354 4 0.314 5 0.281 8

87.90 85.84 83.96 82.00 80.20 78.35 76.60 74.83 73.17 69.58 66.73 63.73 60.86 58.12 55.51

75.83 75.09 74.36 73.62 72.88 72.14 71.40 70.66 69.92 68.45 66.97 65.49 64.01 62.54 61.07

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5.6.1

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Refractive Index

The refractive index n is the ratio of the velocity of light in a particular substance to the velocity of light in vacuum. Values reported refer to the ratio of the velocity in air to that in the substance saturated with air. Usually the yellow sodium doublet lines are used; they have a weighted mean of 589.26 nm and are symbolized by D. When only a single refractive index is available, approximate values over a small temperature range may be calculated using a mean value of 0.000 45 per degree for dn/dt, and remembering that nD decreases with an increase in temperature. If a transition point lies within the temperature range, extrapolation is not reliable. The specific refraction rD is given by the Lorentz and Lorenz equation, RD ⫽

n 2D ⫺ 1 1 · n 2D ⫹ 2 ␳

where ␳ is the density at the same temperature as the refractive index, and is independent of temperature and pressure. The molar refraction is equal to the specific refraction multiplied by the molecular weight. It is a more or less additive property of the groups or elements comprising the compound. A set of atomic refractions is given in Table 5.19; an extensive discussion will be found in Bauer, Fajans, and Lewin, in Physical Methods of Organic Chemistry, 3d ed., A. Weissberger (ed.), vol. 1, part II, chap. 28, Wiley-Interscience, New York, 1960. The empirical Eykman equation n 2D ⫺ 1 1 · ⫽ constant n D ⫹ 0.4 ␳ offers a more accurate means for checking the accuracy of experimental densities and refractive indices, and for calculating one from the other, than does the Lorentz and Lorenz equation. The refractive index of moist air can be calculated from the expression (n ⫺ 1) ⫻ 106 ⫽

103.49 177.4 86.26 p1 ⫹ p2 ⫹ T T T

冉

1⫹

5748 T

冊

p3

where p1 is the partial pressure of dry air (in mmHg), p2 is the partial pressure of carbon dioxide (in mmHg), p3 is the partial pressure of water vapor (in mmHg), and T is the temperature (in kelvins). Example: 1-Propynyl acetate has nD ⫽ 1.4187 and density ⫽ 0.9982 at 20⬚C; the molecular weight is 98.102. From the Lorentz and Lorenz equation, rD ⫽

(1.4187)2 ⫹ 1 1 · ⫽ 0.2528 (1.4187)2 ⫹ 2 0.9982

The molar refraction is MrD ⫽ (98.102)(0.2528) ⫽ 24.80 From the atomic and group refractions in Table 5.19, the molar refraction is computed as follows: 6H 5C 1 C# C 1 O(ether) 1 O(carbonyl)

6.600 12.090 2.398 1.643 2.211 MrD ⫽ 24.942

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TABLE 5.20 Atomic and Group Refractions Group

MrD

Group

MrD

H C Double bond (C " C) Triple bond (C # C) Phenyl (C6 H 5 ) Naphthyl (C10 H 7 ) O (carbonyl) (C " O) O (hydroxyl) (O 9 H) O (ether, ester) (C 9 O 9 ) F (one fluoride) (polyfluorides) Cl Br I S (thiocarbonyl) (C " S) S (thiol) (S 9 H) S (dithia) ( 9 S 9 S 9 ) Se (alkyl selenides) 3-membered ring 4-membered ring

1.100 2.418 1.733 2.398 25.463 43.00 2.211 1.525 1.643 0.95 1.1 5.967 8.865 13.900 7.97 7.69 8.11 11.17 0.71 0.48

N (primary aliphatic amine) N (sec-aliphatic amine) N (tert-aliphatic amine) N (primary aromatic amine) N (sec-aromatic amine) N (tert-aromatic amine) N (primary amide) N (sec amide) N (tert amide) N (imidine) N (oximido) N (carbimido) N (hydrazone) N (hydroxylamine) N (hydrazine) N (aliphatic cyanide) (C # N) N (aromatic cyanide) N (aliphatic oxime) NO (nitroso) NO (nitrosoamine) NO2 (alkyl nitrate) (alkyl nitrite) (aliphatic nitro) (aromatic nitro) (nitramine)

2.322 2.499 2.840 3.21 3.59 4.36 2.65 2.27 2.71 3.776 3.901 4.10 3.46 2.48 2.47 3.05 3.79 3.93 5.91 5.37 7.59 7.44 6.72 7.30 7.51

5.6.2

Surface Tension

The surface tension of a liquid, ␥, is the force per unit length on the surface that opposes the expansion of the surface area. In the literature the surface tensions are expressed in dyn · cm⫺1; 1 dyn · cm⫺1 ⫽ 1 mN · m⫺1 in the SI system. For the large majority of compounds the dependence of the surface tension on the temperature can be given as

␥ ⫽ a ⫺ bt where a and b are constants and t is the temperature in degrees Celsius. The values of a and b given in Tables 5.16 and 5.18 can be used to calculate the values of surface tension for the particular compound within its liquid range. For example, the least-squares constants for acetic anhydride (liquid from ⫺73 to 140⬚C) are 35.52 and 0.1436, respectively. At 20⬚C, ␥ ⫽ 35.52 ⫺ 0.1436(20) ⫽ 32.64 dyn · cm⫺1. A compilation of data of some 2200 pure liquid compounds has been prepared by Jasper, J. Phys. Chem. Reference Data 1:841 (1972).

5.6.3

Dipole Moments

The permanent dipole moment of an isolated molecule depends on the magnitude of the charge and on the distance separating the positive and negative charges. It is defined as

␮⫽

冉冘 冊 qi ri

i

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where the summation extends over all charges (electrons and nuclei) in the molecule. The numerical values of the dipole moment, expressed in the c.g.s. system of units, are in debye units, D, where 1 D ⫽ 10⫺18 esu of charge ⫻ centimeters. The conversion factor to SI units is 1 D ⫽ 3.335 64 ⫻ 10⫺30 C · m

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[coulomb-meter]

Tables 5.17 and 5.18 contain a selected group of compounds for which the dipole moment is given. An extensive collection of dipole moments (approximately 7000 entries) is contained in A. L. McClellan, Tables of Experimental Dipole Moments, W. H. Freeman, San Francisco, 1963. A critical survey of 500 compounds in the gas phase is given by Nelson, Lide, and Maryott, NSRDSNBS 10, Washington, D.C., 1967.

5.6.4

Dielectric Constants

If two oppositely charged plates exist in a vacuum, there is a certain force of attraction between them, as stated by Coulomb’s law: F⫽

1 q1q2 · 4␲␧0 ␧r 2

where F is the force, in newtons, acting on each of the charges q1 and q2 , r is the distance between the charges, ␧ is the dielectric constant of the medium between the plates, and ␧0 is the permittivity of free space. q1 , q2 are expressed in coulombs and r in meters. If another substance, such as a solvent, is in the space separating these charges (or ions in a solution), their attraction for each other is less. The dielectric constant is a measure of the relative effect a solvent has on the force with which two oppositely charged plates attract each other. The dielectric constant is a unitless number. Dielectric constants for a selected group of inorganic and organic compounds are included in Tables 5.17 and 5.18. An extensive list has been compiled by Maryott and Smith, National Bureau Standards Circular 514, Washington, D.C., 1951. For gases the values of the dielectric constant can be adjusted to somewhat different conditions of temperature and pressure by means of the equation (␧ ⫺ 1)t,p (␧ ⫺ 1)20⬚,1

atm

⫽

p 760[1 ⫹ 0.003 411(t ⫺ 20)]

where p is the pressure (in mmHg) and t is the temperature (in ⬚C). The errors associated with this equation probably do not exceed 0.02% for gases between 10 and 30⬚C and for pressures between 700 and 800 mm. The dielectric constants of selected gases will be found in Table. 5.18.

5.6.5

Viscosity

The dynamic viscosity, or coefficient of viscosity, ␩ of a Newtonian fluid is defined as the force per unit area necessary to maintain a unit velocity gradient at right angles to the direction of flow between two parallel planes a unit distance apart. The SI unit is pascal-second or newton-second per meter squared [N · s · m⫺2]. The c.g.s. unit of viscosity is the poise [P]; 1 cP ⬅ 1 mN · s · m⫺2. The dynamic viscosity decreases with the temperature approximately according to the equation: log ␩ ⫽ A ⫹ B/T. Values of A and B for a large number of liquids are given by Barrer, Trans. Faraday Soc. 39:48 (1943).

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TABLE 5.21 Aqueous Glycerol Solutions Viscosity, mN · s · m⫺2

% Weight glycerol

Grams per liter

Relative density 25⬚/25⬚C

20⬚C

25⬚C

30⬚C

100 99 98 97 96 95 80 50 25 10

1261 1246 1231 1216 1201 1186 966.8 563.2 265.0 102.2

1.262 01 1.259 45 1.256 85 1.254 25 1.251 65 1.249 10 1.209 25 1.127 20 1.061 15 1.023 70

1 495 1 194 971 802 659 543.5 61.8 6.032 2.089 1.307

942 772 627 521 434 365 45.72 5.024 1.805 1.149

622 509 423 353 296 248 34.81 4.233 1.586 1.021

Kinematic viscosity v is the ratio of the dynamic viscosity to the density of a fluid. The SI unit is meter squared per second [m2 · s⫺1]. The c.g.s. units are called stokes [cm2 · s⫺1]; poises ⫽ stokes ⫻ density. Fluidity ␾ is the reciprocal of the dynamic viscosity. The primary reference liquid for viscosity measurements is water. The absolute viscosity of water at 20⬚C is 1.0019 (⫾0.0003) mN · s · m⫺2 (or centipoise), as determined by Swindells, Coe, and Godfrey, J. Research Natl. Bur. Standards 48:1 (1952). The relative viscosity of water, ␩/␩20⬚ , is 0.8885 at 25⬚C, 0.7960 at 30⬚C, and 0.6518 at 40⬚C. Values at temperatures between 15 and 60⬚C are best represented by Cragoe’s equation: log

␩ 1.2348(20 ⫺ t) ⫺ 0.001 467(t ⫺ 20)2 ⫽ ␩20⬚ t ⫹ 96

The Reynolds number for flow in a tube is defined by dv␳/␩, where d is the diameter of the tube, v is the average velocity of the fluid along the tube, ␳ is the density of the fluid, and ␩ is its dynamic viscosity. At flow velocities corresponding with values of the Reynolds number of greater than 2000, turbulence is encountered.

TABLE 5.22 Aqueous Sucrose Solutions Viscosity, mN · s · m⫺2

% Weight sucrose

Grams per liter

Relative density 20⬚/4⬚C

15⬚C

20⬚C

25⬚C

75 70 65 60 50 40 30

1034 943.0 855.6 771.9 614.8 470.6 338.1

1.379 0 1.347 2 1.316 3 1.286 5 1.299 6 1.176 4 1.127 0

4 039 746.9 211.3 79.49 19.53 7.463 3.757

2 328 481.6 147.2 58.49 15.43 6.167 3.187

1 405 321.6 105.4 40.03 12.40 5.164 2.735

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COMBUSTIBLE MIXTURES

TABLE 5.23 Properties of Combustible Mixtures in Air The autoignition temperature is the minimum temperature required for self-sustained combustion in the absence of an external ignition source. The value depends on specified test conditions. The flammable (explosive) limits specify the range of concentration of the vapor in air (in percent by volume) for which a flame can propagate. Below the lower flammable limit, the gas mixture is too lean to burn; above the flammable limit, the mixture is too rich. Additional compounds can be found in National Fire Protection Association, National Fire Protection Handbook, 14th ed., 1991. For alternative nomenclature, see Table 1.15. Flammable (explosive) limits, percent by volume of fuel (25⬚C, 760 mm) Substance Acetaldehyde Acetanilide Acetic acid, glacial Acetic anhydride Acetone Acetonitrile Acetophenone Acetylacetone Acetylene Acetyl chloride Acrolein Acrylic acid (2-propenoic acid) Acrylonitrile Adiponitrile Allyl acetate Allyl alcohol Allylamine Ammonia, anhydrous Aniline Asphalt Benzaldehyde Benzene Benzoyl peroxide Benzyl acetate Benzyl alcohol Benzyl benzoate Benzyl chloride Bis(2-aminoethyl)amine Bis(2-chloroethyl) ether Biscyclohexyl Bis(2-hydroethyl) ether Bromobenzene 1-Bromobutane Bromoethane Bromomethane 1-Bromopropane

Autoignition temperature, ⬚C 175 540 463 316 465 524 570 340 305 390 220 438 481 550 374 378 374 651 615 485 192 498 80 460 436 480 585 399 369 245 229 565 265 511 537 490

Lower

Upper

4.0

60

4.0 2.7 2.5 3.0

19.9 10.3 12.8 16.0

3.0

65

2.8 2.4 3.0 2

31.0 8.0 17.0 5

2.5 2.2 16 1.3

18.0 22 25 11

1.2

7.8

1.1 2.7 0.7

5.1

2.6 6.8 10

6.6 8.0 16.0

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TABLE 5.23 Properties of Combustible Mixtures in Air (Continued) Flammable (explosive) limits, percent by volume of fuel (25⬚C, 760 mm) Substance 3-Bromopropene 1,3-Butadiene Butanal (butyraldehyde) Butane 1,3-Butanediol 2,3-Butanediol Butanenitrile Butanoic acid (butyric acid) Butanoic anhydride (butyric anhydride) 1-Butanol 2-Butanol 2-Butanone trans-2-Butenal (crotonaldehyde) 1-Butene cis-2-Butene trans-2-Butene 1-Butene oxide 3-Buten-1-ol 2-Butoxyethanol 2-(2-Butoxyethoxy)ethyl acetate Butyl acetate sec-Butyl acetate Butylamine tert-Butylamine Butylbenzene sec-Butylbenzene tert-Butylbenzene Butyl formate Butyl methyl ketone Butyl 2-methyl-2-propenoate Butyl propanoate Butyl stearate Butyl vinyl ether 2-Butyne Camphor Carbon disulfide Carbon monoxide Carbonyl sulfide Chlorobenzene 1-Chloro-1,3-butadiene 1-Chlorobutane 2-Chloro-2-butene 1-Chloro-2,3-epoxypropane 1-Chloro-1,1-difluoroethane 1-Chloro-2,4-dinitrobenzene 1-Chloro-2,3-epoxypropane Chloroethane 2-Chloroethanol Chloromethane 1-Chloro-3-methylbutane 1-Chloro-2-methylpropane

Autoignition temperature, ⬚C 295 420 218 287 395 402 501 443 279 343 415 404 232 384 324 324 238 299 425 312 380 410 418 450 322 423 294 427 355 255 466 90 609 593 240 411 411 519 425 632

Lower

Upper

4.4 2.0 1.9 1.9

7.3 11.5 12.5 8.5

1.65 2.0 0.9 1.4 1.7 1.4 2.1 1.6 1.7 1.8 1.5 4.7 4

10.0 5.8 11.2 11 11.4 15.9 9.3 9.7 18.3 34 13

1.7 1.7 1.7 1.7 0.8 0.8 0.7 1.7 1 2

7.6 9.8 9.8 8.9 5.8 6.9 5.7 8.2 8 8

1.4 0.6 1.3 12.5 12 1.3 4.0 1.8 2.3 4 6.2 2.0 3.8 3.8 4.9 8.1 1.5 2.0

3.5 50.0 74.2 28.5 9.6 20.0 10.1 9.3 21 17.9 22 21 15.4 15.9 17.4 7.4 8.8

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TABLE 5.23 Properties of Combustible Mixtures in Air (Continued) Flammable (explosive) limits, percent by volume of fuel (25⬚C, 760 mm) Substance 3-Chloro-2-methyl-1-propene 1-Chloronaphthalene 1-Chloropentane 1-Chloropropane 2-Chloropropane 1-Chloro-1-propene 2-Chloro-1-propene 3-Chloro-1-propene Chlorotrifluoroethylene m-Cresol o-Cresol p-Cresol Cumene Cyanogen Cyclobutane Cyclohexane Cyclohexanol Cyclohexanone Cyclohexene Cyclohexyl acetate Cyclohexylamine Cyclopentane Cyclopentene Cyclopropane p-Cymene trans-Decahydronaphthalene Decane Decene Diborane(6) Dibutylamine Dibutyl decanedioate (dibutyl sebacate) Dibutyl ether Dibutyl o-phthalate 1,2-Dichlorobenzene 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene Dichloromethane 1,2-Dichloropropane Diethanolamine [2,2⬘-iminobis(ethanol)] 1,1-Diethoxyethane (acetal) Diethylamine Diethylene glycol [bis(2-hydroxyethyl) ether] Diethylene glycol dibutyl ether Diethylene glycol monoethyl ether acetate Diethylene glycol monomethyl ether Diethylenetriamine Diethyl ether 3,3-Diethylpentane

Autoignition temperature, ⬚C ⬎588 260 520 593 485 558 599 558 424 245 300 420 244 334 293 361 395 500 436 255 210 235 38 to 52 365 194 402 648 458 413 570 460 460 556 557 662 230 312 224 310 425 240 358 180 290

Lower

Upper

2.3

9.3

1.6 2.6 2.8 4.5 4.5 2.9 24 1.1 1.4 1.1 0.9 6.6 1.8 1.3 1 1.1 1.2

8.6 11.1 10.7 16 16 11.1 40.3

1 1.5

9

2.4 0.7 0.7 0.8

10.4 5.6 5.4 5.4

6.5 32 8 9 9.4

0.8 1.1 0.44 1.5 0.5 2.2 5.4 6.2 6.5 3 6 13 3.4 2 1.6 1.8 2

88 6

9.2 11.4 16 15.5 15 13 23 14.5 13 10.4 10.1 17

1.4 2 1.9 0.7

22.7 6.7 36.0 5.7

7.6

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TABLE 5.23 Properties of Combustible Mixtures in Air (Continued) Flammable (explosive) limits, percent by volume of fuel (25⬚C, 760 mm) Substance Diethyl peroxide Diethyl sulfate 1,1-Difluoroethylene 1,3-Dihydroxybenzene (resorcinol) 1,4-Dihydroxybenzene Diisopropylamine Diisopropyl ether Dimethoxymethane N,N-Dimethylacetamide Dimethylamine (anhydrous) N,N-Dimethylaniline 2,3-Dimethylaniline 2,2-Dimethylbutane 2,3-Dimethylbutane 3,3-Dimethyl-2-butanone cis-1,2-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane Dimethyl ether N,N-Dimethylformamide 2,6-Dimethyl-4-heptanol 2,6-Dimethyl-4-heptanone 2,3-Dimethylhexane 1,1-Dimethylhydrazine 2,3-Dimethylpentane Dimethyl 1,2-phthalate 2,2-Dimethylpropane Dimethyl sulfate Dimethyl sulfide Dimethyl sulfoxide 1,4-Dioxane Dipentene Dipentyl ether Diphenylamine Diphenyl ether Dipropylamine Dipropyl ether Divinyl ether Dodecane 1-Dodecanol 1,2-Epoxybutane Ethane 1,2-Ethanediamine 1,2-Ethanediol Ethanethiol Ethanol Ethanolamine 2-Ethoxyethanol 2-Ethoxyethyl acetate 1-Ethoxypropane Ethyl acetate Ethyl acetoacetate

Autoignition temperature, ⬚C

Lower

Upper

2.3

15.9

5.5

21.3

1.1 1.4 2.2 2.0 2.8

7.1 7.9 13.8 11.5 14.4

1.0 1.2 1.2 1

7.0 7.0 8

3.4 2.2 0.8 0.8

27.0 15.2 6.1 6.2

2 1.1 0.9 1.4

95 6.7

2.2 2.6 2.0

19.7 42 22

0.8

1.5

1.3 1.7 0.6

7.0 27.0

1.7 3.0 2.5 3.2 2.8 3.3 3.0 3 2 1.7 2 1.4

19 12.5 12.0 22 18.2 19 23.5 18 8 9.0 11.5 9.5

436 664 516 316 443 237 490 400 371 405 405 423 304 304 350 445 396 438 249 335 490 450 188 206 215 180 237 170 634 618 299 188 360 203 275 439 515 385 398 299 363 410 235 379 426 295

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TABLE 5.23 Properties of Combustible Mixtures in Air (Continued) Flammable (explosive) limits, percent by volume of fuel (25⬚C, 760 mm) Substance Ethyl acrylate Ethylamine Ethylbenzene Ethyl benzoate Ethyl butanoate 2-Ethylbutanoic acid Ethyl chloroformate Ethylcyclobutane Ethylcyclohexane Ethylene Ethylene glycol diacetate Ethylene glycol dimethyl ether Ethylene glycol ethyl ether acetate Ethylene glycol monobutyl ether Ethylene glycol methyl ether acetate Ethylene glycol monoethyl ether Ethyleneimine Ethylene oxide Ethyl formate 2-Ethylhexanal 2-Ethyl-1,3-hexanediol 2-Ethyl-1-hexanol 2-Ethylhexyl acetate Ethyl lactate Ethyl methyl ether 3-Ethyl-2-methylpentane Ethyl nitrate Ethyl nitrite Ethyl propanoate Ethyl vinyl ether Formaldehyde Formic acid, 90% 2-Furaldehyde (furfural) Furan Furfuryl alcohol Gasoline, 50-100 octane Glycerol Heptane 2-Heptanone (methyl pentyl ketone) 4-Heptanone (diisobutyl ketone) 1-Heptene 1,1,2,3,4,4-Hexachlorobutadiene Hexane 1,6-Hexanedioic acid Hexanoic acid 2-Hexanone 1-Hexene Hydrazine Hydrogen Hydrogen cyanide, 96% Hydrogen sulfide

Autoignition temperature, ⬚C 372 385 432 490 463 463 500 210 238 490 482 202 379 238 392 235 320 429 455 197 360 231 268 400 460 85 explodes 90 explodes 440 202 430 434 316 491 280 to 456 370 204 393 396 260 610 225 420 380 423 253 23 to 270 400 538 260

Lower

Upper

1.4 3.5 0.8

14 14.0 6.7

1.2 0.9 2.7 1.6

7.7 6.6 36.0 8.4

2 4 2 3 3.3 3.0 2.8

8 13 12 18 54.8 100 16.0

0.88 0.76 1.5 2.0

10.0

3.8 3.0 1.9 1.7 7.0 18 2.1 2.3 1.8 1.4 3 1.05 1.1 0.8

50.0 11 28 73.0 57 19.3 14.3 16.3 7.6 19 6.7 7.9 7.1

1.1

7.5

1

8

4.7 4.1 5.6 4

9.7 8.14

100 74.2 40.0 46

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TABLE 5.23 Properties of Combustible Mixtures in Air (Continued) Flammable (explosive) limits, percent by volume of fuel (25⬚C, 760 mm) Substance N-Hydroxyethyl-1,2-ethanediamine 1-Hydroxy-2-methylbenzene 1-Hydroxy-3-methylbenzene 1-Hydroxy-4-methylbenzene (see p-cresol) 4-Hydroxy-4-methyl-2-pentanone Isobutanal Isobutyl acetate Isobutylamine Isobutylbenzene Isobutyl isobutyrate Isopentane Isopentyl acetate Isoprene Isopropyl acetate Isopropyl alcohol Isopropylamine Isopropylbenzene (cumene) Isopropyl formate 4-Isopropyl-1-methylbenzene Kerosene Maleic anhydride Methacrylic acid Methacrylonitrile Methane Methanethiol Methanol Methoxybenzene (anisole) 2-Methoxyethanol 2-Methoxyethyl acetate Methyl acetate Methyl acetoacetate Methyl acetylacetate Methyl acrylate Methylamine 2-Methylbutane 2-Methyl-1-butanol 2-Methyl-2-butanol 3-Methyl-1-butanol 3-Methylbutyl acetate 2-Methyl-2-butene 3-Methyl-1-butene 2-Methyl-1-buten-3-one Methyl chloroformate Methylcyclohexane cis-2-Methylcyclohexanol trans-2-Methylcyclohexanol cis-4-Methylcyclohexanol trans-4-Methylcyclohexanol Methylcyclopentane Methyl formate 2-Methylhexane

Autoignition temperature, ⬚C 368 599 559 643 196 421 378 427 432 420 360 220 460 399 402 424 485 436 210 477 68 650 464 475 285 392 454 280 280 468 430 385 437 350 360 275 365 504 250 296 296 295 295 258 449 280

Lower

Upper

1.4 1.1 1.8 1.6 1 2 0.8 0.96 1.4 1.0 2 1.8 2.5 2.3 0.8

6.9 10.6 10.5 12 6.0 7.59 7.6 7.5 9 8 12.7 10.4 6.5

0.7 1.4 1.6 2 5.3 3.9 6.0

5.0 7.1 8.8 6.8 15.0 21.8 36

1.8 1.5 3.1

14 12.3 16

2.8 4.9 1.4 1.4 1.2 1.2 1.0 1.6 1.5 1.8

25 20.7 7.6 9.0 9.0 9.0 7.5 8.7 9.1 9.0

1.2

6.7

1.0 4.5 1.0

8.35 23 6.0

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PHYSICAL PROPERTIES

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TABLE 5.23 Properties of Combustible Mixtures in Air (Continued) Flammable (explosive) limits, percent by volume of fuel (25⬚C, 760 mm) Substance 3-Methylhexane 5-Methyl-2-hexanone Methylhydrazine Methyl isobutyl ketone (MIBK) 2-Methyllactonitrile Methyl methacrylate 1-Methyl-4-(1-methylethenyl)-cyclohexene (dipentene) 1-Methylnaphthalene 2-Methylpentane 3-Methylpentane 2-Methyl-2,4-pentanediol 2-Methyl-1-pentanol 4-Methyl-2-pentanol 4-Methyl-2-pentanone 4-Methyl-3-penten-2-one 2-Methylpropanal 2-Methyl-1-propanamine 2-Methylpropane 2-Methylpropanenitrile Methyl propanoate 2-Methylpropanoic acid 2-Methyl-1-propanol 2-Methyl-2-propanol (t-butyl alcohol) 2-Methyl-1-propene 2-Methylpropyl acetate 2-Methylpropyl formate 2-Methylpyridine N-Methyl-2-pyrrolidone Methyl salicylate ␣-Methylstyrene Methyl vinyl ether Morpholine Naphtha, coal tar Naphthalene Neoprene Nicotine Nitrobenzene 2-Nitrobiphenyl Nitroethane Nitroglycerine Nitromethane 1-Nitropropane 2-Nitropropane Nonane Octadecanoic acid (stearic acid) cis-9-Octadecenoic acid (oleic acid) Octane 1-Octene Paraldehyde Pentaborane(9) Pentanamine

Autoignition temperature, ⬚C 280 191 196 448 688 237 529 264 278 306 310 452 344 223 378 460 482 469 481 415 478 465 421 320 538 346 454 574 290 277 526 244 482 179 414 270 418 421 428 205 395 362 206 230 238

Lower

Upper

1.0 2.5 1

8.2 97.⫾2 8

1.7

8.2

1.0 1.2 1 1.1 1.0 2 1.4 1.6 2 1.8

7.0 7.0 9 9.65 5.5 8.0 7.2 10.6 12 8.4

2.5 2.0 1.7 2.4 1.8 1.3 1.7

13 9.2 10.6 8.0 9.6 10.5 8

1

10

1.9 2.6 1

6.1 39 11

0.9 4.0 0.75 1.8

5.9 20 4.0 9

3.4

17

7.3 2.2 2.6 0.8

22 11 2.9

1.0

6.5

1.3 0.42 2.2

22

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TABLE 5.23 Properties of Combustible Mixtures in Air (Continued) Flammable (explosive) limits, percent by volume of fuel (25⬚C, 760 mm) Substance Pentane 1,5-Pentanediol Pentanoic acid 1-Pentanol 2-Pentanol 3-Pentanol 2-Pentanone (methyl propyl ketone) 3-Pentanone (diethyl ketone) 1-Pentene Pentyl acetate Pentylamine Petroleum ether (solvent naphtha) Phenol Phosphorus, red Phosphorus, white Phosphorus pentasulfide o-Phthalic anhydride Picric acid ␣-Pinene ␤-Pinene Piperidine 1-Propanal 1-Propanamine (propylamine) Propane 1,2-Propanediol 1,3-Propanediol Propanenitrile 1,2,3-Propanetriol (glycerol) 1,2,3-Propanetriol triacetate (triacetin) Propanoic acid Propanoic anhydride 1-Propanol 2-Propanol Propene Propyl acetate Propylbenzene Propyl formate Propyl nitrate Propyne Pyridine Quinoline Sodium Styrene Sulfur (di-) dichloride 1,1,2,2-Tetrabromoethane Tetrabromoethylene 1,1,1,2-Tetrachloroethane

Autoignition temperature, ⬚C 260 335 400 300 343 435 452 450 275 360 288 715 260 30 142 570 300 (explodes) 275 275 207 318 450 371 400 512 370 433 465 285 412 399 460 450 450 455 175 482 480 115 (dry air) 490 233 335 335

Lower

Upper

1.5

7.8

1.2

10.0

1.2 1.5 1.6 1.5 1.1 2.2 1.1 1.8

9.0 8.2 8.7 7.5 22 5.9 8.6

1.7

10.4

1 2.6 2.0 2.1 2.6

10 17 10.4 9.5 12.5

3.1 3 1.0 2.9 1.3 2.2 2.0 2.4 1.7 0.8

14 19

2 1.7 1.8

100

0.9

5

12.1 9.5 13.7 12.7 10.1 8 6.0

12.4

6.8

12

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PHYSICAL PROPERTIES

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TABLE 5.23 Properties of Combustible Mixtures in Air (Continued) Flammable (explosive) limits, percent by volume of fuel (25⬚C, 760 mm) Substance 1,1,2,2-Tetrachloroethane Tetrahydrofuran Tetrahydrofurfuryl alcohol 1,2,3,4-Tetrahydronaphthalene 2,2,3,3-Tetramethylpentane 2,2-Thiodiethanol Titanium, powder Toluene Toluene diisocyanate o-Toluidine (also p-) Tributylamine 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene (Trichloromethyl)benzene Trichloromethylsilane 1,2,3-Trichloropropane Trichlorosilane 1,1,2-Trichloro-1,2,2-trifluoroethane (Freon 113) Tri-o-cresyl phosphate Triethanolamine Triethylamine Triethylene glycol Triethyl phosphate Trimethylamine 1,2,3-Trimethylbenzene (hemimellitene) 1,2,4-Trimethylbenzene (pseudocumene) 1,3,5-Trimethylbenzene 2,2,3-Trimethylbutane 1,1,3-Trimethyl-3-cyclohexen-5-one 3,5,5-Trimethylcyclohex-2-ene-1-one 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane Trioxane Tri-o-tolyl phosphate Turpentine Vinyl acetate Vinyl bromide Vinyl butanoate Vinyl chloride 4-Vinyl-1-cyclohexene Vinyl fluoride Vinylidene m-Xylene o-Xylene p-Xylene

Autoignition temperature, ⬚C

321 282 385 430 298 250 480

Lower

Upper

20 2 1.5 0.8 0.8

54 11.8 9.7 5.0 4.9

1.1 0.9

7.1 9.5

1 7.5 6 8

5 12.5 28 10.5

7.6 3.2

⬎20 12.6

1 1.2 0.9

10 8.0 9.2

2.0 0.8 0.9 1

11.6 6.6 6.4 5

0.8 0.8

3.8 3.8

1.1

6.0

3.6

28.7

0.8 2.6 9 1.4 3.6

13.4 15 8.8 33.0

2.6 5.6 1.1 0.9 1.1

21.7 16.0 7.0 6.7 7.0

482 537 460 420 211 ⬎404 104 680 385 249 371 454 190 470 500 559 412 462 460 346 418 425 414 385 402 530 472 269 573 527 463 528

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THERMAL CONDUCTIVITY

TABLE 5.24 Thermal Conductivities of Gases as a Function of Temperature

(McGHP)

The coefficient k, expressed in J · sec⫺1 · cm⫺1 · K⫺1, is the quantity of heat in joules, transmitted per second through a sample one centimeter in thickness and one square centimeter in area when the temperature difference between the two sides is one degree kelvin (or Celsius). The tabulated values are in microjoules. To convert to microcalories, divide values by 4.184. To convert to mW · m⫺1 · K⫺1, divide values by 10. Temperature, ⬚C Substance

⫺20 80

118⫺75 164⫺60

72 103

20

40

60

80

100

120

95

107 109

124 126 224 270 259 186

173 176 137 290 311 321 211 165

207

205 256 238 176

156 159 124 269 299 301 206 146

190 195 151

184 242 218 166

140 142 112 248 284 280 196 126

324

336

342149

184

205 241

226

42

186 45

50 82

54 94

59 104

174 176 85 262 70 93 122 120 75 117 120

193 192

213 207

117 176110 233 215

278 75 100

80

86

134 84 130 141 192

151 91 142 163 218

167 99 155 184 243

1356.5 135 144 67 228 59 79 110 90

154 160 76 245 64 85 116 105

84 77

105 99

140

160

166

109184

186 107

204 116

206 270

230

INTERACTIVE

64

0

LEFT

Acetone Acetaldehyde Acetonitrile Acetylene Air Ammonia Argon Benzene Boron trifluoride Bromine Bromomethane 1-Butanamine Butane Carbon dioxide Carbon disulfide Carbon monoxide Carbon tetrachloride Chlorine Chlorodifluorimethane Chloroethane Chloroform Chloromethane Cyclohexane Cyclopropane

⫺40

256

5.148

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Temperature, ⬚C Substance

1150

⫺20 1222

0

20

40

60

1297

1372

1448

1523

80

100

120

140

358220

263 74110 81

91

92 81

100 93

94 93

97

100

105

117

138 129 127 161

99

137

137

159

158

230 1343

1494 64 107

1607 70 117 99 116

135

157

182 126

204 141

136 178

153 220

228 155 23049 115 169 241

79

100

247 1423 100 109 1724 77 128 110 129 46 85 307 67 122 141

179 178

199 200

257

288

133 206 262

151 282

121

142

164

264 1481 115

278 1540 130

294 1598

309 1661

1828 84 138 121 143 53

1925 90 148 132 156 60 95 361

2025 97

178

334

156

176

211227

153 243 244 187 344

268 269 207

351213

170

191

211

234

193 186 159 325 1720 174 201

256 206 178

279 226 197

218 222 167 316 209

1778 224

247

104 240227

191 143 169 68 387 174 15070 196

271

75 416 197

82 110 445 221 177 215 23393

89

241 195 271

263 215

284 237 421227

INTERACTIVE

257

79 280

118 113

RIGHT

212 1276

194200 144 140

(McGHP)

84 69

160

DEAN #37261

Deuterium Deuterium oxide Dibromomethane Dichlorodifluoromethane 1,1-Dichloroethane 1,2-Dichloroethane Dichlorofluoromethane Dichloromethane 1,2-Dichlorotetrafluoroethane Diethylamine Diethyl ether 1,4-Dioxane Ethane Ethanol Ethene Ethyl acetate Ethylamine Ethylene Ethylene oxide Ethyl formate Ethyl nitrate Fluorine Helium Heptane Hexane Hydrogen Hydrogen bromide Hydrogen chloride Hydrogen cyanide Hydrogen sulfide Iodomethane Krypton Methane Methanol Methyl acetate 2-Methylbutane 2-Methylpropane

⫺40

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DEAN #37261

TABLE 5.24 Thermal Conductivities of Gases as a Function of Temperature (Continued) Temperature, ⬚C Substance

⫺20

0

20

40

60

80

100

410 205 211

433 221 226

454 238 241

476 254 256

497 269 270

518 285 282

537 301 295

225 556 317 307

121

137

152

184

211

228

278

294

311

116

132

245 130 151

168 120 261 171 15131

192

215

238

83

120

140

160

333 155

385227

330

353 250127

379

201 235

275227

338327

320 139

(McGHP)

190

163

328 218 262 106

126 235 152110 87 142 36⫺73

159

175 54

191

207

224

195 241

133 216 257 72

239 89227

104327

LEFT

2-Methyl-2-propanol Neon Nitric oxide Nitrogen Nitromethane Nitrous oxide Octafluorocyclobutane Oxygen Pentane Propane 2-Propanol Sulfur dioxide Sulfur hexafluoride Tetrafluoromethane Thiophene 1,1,2-Trichlorotrifluoroethane Triethylamine Water Xenon

⫺40

INTERACTIVE

5.150

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RIGHT

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PHYSICAL PROPERTIES

top of rh base of rh cap height base of text

TABLE 5.25 Liquid Thermal Conductivity of Various Substances All values of thermal conductivity, k, are in millijoules cm⫺1 · s⫺1 · K⫺1. To convert to mJ · cm⫺1 · s⫺1 · K⫺1 into mW · m⫺1 · K⫺1, divide by 10. Thermal conductivity in mJ · cm⫺1 · s⫺1 · K⫺1 Substance Acetaldehyde Acetic acid Acetic anhydride Acetone Acetonitrile Allyl alcohol Aniline Argon Benzaldehyde Benzene Bromobenzene Bromoethane 1-Bromo-2-methylpropane 1-Bromopentane Bromopropane Butanoic acid 1-Butanol 2-Butanone Butyl acetate 2-Butyne Carbon disulfide Carbon tetrachloride Chlorobenzene Chloroethane Chloroform (Chloromethyl)oxirane 1-Chloro-2-methylpropane 1-Chloropentane Chloropropane 4-Chlorotoluene m-Cresol Cyclohexane Cyclohexene Cyclohexanol Cyclopentane Cyclopentene Decane 1-Decanol Dibromomethane Dibutyl phthalate 1,2-Dichloroethane Dichlorofluoromethane Dichloromethane Diethyl ether Diisopropyl ether 2,3-Dimethylbutane N,N-Dimethylformamide Dimethyl phthalate

⫺25⬚C

0⬚C

20⬚C

25⬚C

50⬚C

75⬚C

1.58

1.53

1.49

1.5140 1.78

1.68

1.51 1.411

1.41 1.329

1.31 1.247

1.54 1.45

1.49 1.39

1.33

0.974 1.22 1.06 1.12 1.25

1.17 0.93 1.07 1.19

100⬚C

1.900

1.987⫺80 2.08

1.69 1.98

2.209 1.61 1.88 1.8030

1.44

1.7717 1.259⫺189 1.21

1.113 1.029 1.16312 0.983

1.58

1.07512 1.50612 1.538 1.51 1.368

1.37 1.100⫺20 1.36 1.45 1.27 1.42

1.29 1.54 1.071 1.31 1.32 1.22 1.37 1.16312 1.18412 1.18412

1.21 1.49 1.029 1.27 1.19 1.17 1.31

1.297 1.498 1.243 1.42

1.36

1.40 1.43 1.44

1.33 1.36 1.38

1.20 1.44

1.14 1.40 1.264

0.134 1.590⫺20 1.50

1.564 1.40

1.17 1.24 1.31

1.12 1.02 1.14

1.45280 1.11 1.18

1.23 1.30 1.34 1.26 1.29 1.32 1.62 1.08 1.36

1.26 1.56 1.03 1.33

1.19 1.50 0.97 1.29

1.25

1.30

1.20

1.10

1.00

1.03832 1.84 1.473

0.996 1.78 1.443

1.71 1.409

1.65 1.373

1.13 1.45

1.477 1.096

1.501

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TABLE 5.25 Liquid Thermal Conductivity of Various Substances (Continued) Thermal conductivity in mJ · cm⫺1 · s⫺1 · K⫺1 Substance 1,4-Dioxane Diphenyl ether Dodecane 1-Dodecanol Ethanol Ethanolamine Ethoxybenzene Ethyl acetate Ethylbenzene Ethylene glycol Ethyl formate Furan Glycerol Heptane 1-Heptanol Hexadecane Hexane 1-Hexanol 2-Hexanone 1-Hexene Hydrochloric acid, 38% Hydrogen Iodobenzene Iodoethane 1-Iodo-2-methylpropane 1-Iodopentane Iodopropane Isopentyl acetate Isopropylbenzene Mercury Methanol Methoxybenzene Methyl acetate Methyl butanoate 3-Methylbutanoic acid 3-Methyl-1-butanol Methylcyclohexane Methylcyclopentane N-Methylformamide 1-Methyl-4-isopropylbenzene 2-Methylpentane Methyl pentanoate 4-Methylpentanoic acid 4-Methyl-3-pentene-2-one 2-Methyl-1-propanol 2-Methyl-2-propanol Nitrobenzene Nitromethane Nonane

⫺25⬚C

0⬚C

20⬚C

1.57 1.76

25⬚C

50⬚C

75⬚C

100⬚C

1.59 1.52 1.46 1.69 2.99

1.47 1.39 1.46 1.42 1.62 2.86

1.35 1.35 1.40 1.39

1.23 1.31 1.35 1.35

2.74

2.61

1.44 1.30 2.56

1.35 1.24 2.56

1.26 1.18 2.56

1.12 2.56

1.26 2.92 1.228 1.59 1.40 1.20 1.50 1.39 1.21

2.95 1.152 1.53 1.35 1.11 1.45 1.33 1.13

2.97 1.077 1.47 1.30 1.92 1.41 1.27

1.497 1.62

1.53

1.42

2.56 1.58112 1.34

1.378

1.37 1.59 1.51 1.37

1.303 1.66

1.259

1.28 1.54 1.45 1.29

1.218

3.00 1.41 1.25 0.93 1.37 1.21

4.40232 1.180⫺253 1.063⫺20

0.93780

1.276 1.10930 0.87012 0.84912 0.92012 1.297

72.5 2.14 1.70 1.74

77.7 2.07 1.63 1.64

2.021

1.28 82.5 2.00 1.56 1.53

1.20 86.8 1.93 1.50 1.43

1.12 90.7

1.07 94.3

1.43 1.33

1.36 1.22

1.402 1.305

1.32

1.70

1.27 1.31812 1.42712 1.63 1.42312

1.47730 1.27630 1.209 2.03 1.22 1.08432

1.15138 2.01 1.17 1.033

1.99 1.12

1.96 1.07

1.56

1.49

1.42

1.34

1.15938

1.06777

1.510 1.44

1.38

2.15130 1.31

1.24

1.15180

1.11

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PHYSICAL PROPERTIES

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TABLE 5.25 Liquid Thermal Conductivity of Various Substances (Continued) Thermal conductivity in mJ · cm⫺1 · s⫺1 · K⫺1 Substance 1-Nonanol Octadecane Octane 1-Octanol Palmitic acid Pentachloroethane Pentane Pentanoic acid 1-Pentanol 1-Pentene Pentyl acetate Phenol Phenylhydrazine 1,2-Propanediol Propanoic acid 1-Propanol 2-Propanol 1,2-Propylene glycol Propyl formate Pyridine Silicon tetrachloride Sodium Sodium chloride (aq, satd) Stearic acid Styrene Sulfuric acid, 90% 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetrachloromethane Tetradecane 1-Tetradecanol Tetrahydrofuran Thiophene Toluene 1,1,1-Trichloroethane Trichloroethylene Trichloromethane Tridecane Triethylamine Trimethylamine 1,3,5-Trimethylbenzene 2,2,4-Trimethylpentane Undecane Water m-Xylene o-Xylene p-Xylene

⫺25⬚C

0⬚C

20⬚C

1.66 1.43

1.32

1.31

1.35 1.68

1.22 1.36012 1.57 1.24

25⬚C

50⬚C

1.61

75⬚C

100⬚C

1.49 1.42 1.13 1.47 1.598

1.43 1.37 1.06 1.41

0.87

1.657

1.28 1.61

1.55 1.46 1.20 1.54

1.251 1.138

1.13

1.03

0.95

1.53 1.16

1.49

1.45

1.289

1.62 1.46

2.02 1.72812 1.58 1.41 2.008 1.49412 1.69

1.56

1.53

1.51

1.724 2.00

1.99

1.98

1.97

1.54 1.35

1.49 1.29

1.45 1.24

1.41 1.18

1.65 0.99

1.61 0.96

1.58 753.1300

5.732 1.48

1.42

1.37 3.54032

1.31

1.04 0.93 1.36

0.97 0.88 1.31 1.67 1.14 1.95 1.236

1.598 1.26

1.20

1.26 1.62

1.21 1.57

1.91 1.161

1.86

1.138 1.17 1.04

1.10 0.99

1.32

1.26

1.590⫺80 1.06 1.359⫺60 1.27

1.386

1.464⫺80 1.43 1.47

1.347 1.01

1.24 1.22

1.20 1.99 1.311 0.96 1.160 1.17 1.37

1.209 1.33 1.41

5.610

5.983

1.36 0.96638 1.40 6.071 1.30 1.31 1.30

1.08 1.12 1.32 1.11344

1.00 1.07 1.27

1.30

1.24 0.84177 1.29 6.668 1.18 1.20 1.18

1.35 6.435 1.24 1.26 1.24

1.22

1.18 1.23 6.791 1.13 1.14 1.12

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TABLE 5.26 Thermal Conductivity of Various Solids All values of thermal conductivity, k, are in millijoules cm⫺1 · s⫺1 · K⫺1. To convert to mW · m⫺1 · K⫺1m, divide values by 10. For values in millicalories, divide by 4.184. Substance Asphalt Basalt Bauxite Boiler scale Brick, common Blotting paper Cardboard Cement, Portland Chalk Chemical elements, see Table 4.1 Coal Concrete Cork, sp. grav. ⫽ 0.2 Cork meal Cotton, sp. grav. ⫽ 0.081 Diatomaceous earth Ebonite Eiderdown Feathers (with air) Feldspar Felt (dark gray) Fire brick Flannel Flint Glass, crown flint Jena quartz soda Granite Graphite, sp. grav. ⫽ 1.58 Graphite powder, sp. grav. ⫽ 0.7 Gypsum Horse hair, sp. grav. ⫽ 0.172 Ice Leather, cowhide Linen Magnesia brick Marble, white Mica Naphthalene Paper Paraffin Plaster of Paris Porcelain Quartz, parallel to axis

t, ⬚C

k

20 20 600 66 20 20 20 90 20

7.447 21.76 5.56 13.1 6.3 0.628 2.1 2.97 9.2

0 20 30 100 0 20 0 20 9 20 40 20 60 20 12.5 12.5 22 0 100 20 100 20 50 40 0 20 84 20 20 1130 41 0 20 0 20 95 0 100

1.69 9.2 0.54 0.556 0.569 0.54 1.58 0.046 0.238 23.4 0.623 4.6 0.148 10.0 6.82 5.98 9.50 13.89 19.12 7.1 7.5 34.2 441.4 11.92 13.0 0.510 23.8 1.76 0.879 11.3 30.1 32.6 3.60 3.77 1.3 2.88 2.93 10.38 136.0 90.0

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TABLE 5.26 Thermal Conductivity of Various Solids (Continued) Substance Quartz, perpendicular to axis Plastics, see Section 10 Roofing paper Rubber, natural and synthetic, see Section 10 Sand, dry Sandstone, sp. grav. ⫽ 2.259 Silk, sp. grav. ⫽ 0.101 Slate Soil, dry Wax, bees Wood, maple, parallel to face perpendicular to face Wood, oak, parallel to face perpendicular to face Wood, pine, parallel to face perpendicular to face

5.9

top of rh base of rh

t, ⬚C

k

0 100

72.43 55.77

0

1.90

20 40 0 20 20 20 20 50 15 15 20 15

3.89 18.37 0.510 19.66 1.38 0.866 4.25 1.82 3.49 2.09 3.49 1.51

MISCELLANY

TABLE 5.27 Compressibility of Water In the table below are given the relative volumes of water at various temperatures and pressures. The volume at 0⬚C and one normal atmosphere (760 mm of Hg) is taken as unity. P, atm

⫺10⬚C.

0⬚C.

10⬚C.

20⬚C.

40⬚C.

60⬚C.

80⬚C.

1 500 1000 1500 2000 2500 3000 3500 4000 4500 5000 6000 7000 8000 9000 10000 11000 12000

1.0017 0.9788 0.9581 0.9399 0.9223 0.9083 0.8962 0.8852 0.8751 0.8658 0.8573 ...... ...... ...... ...... ...... ...... ......

1.0000 0.9767 0.9566 0.9394 0.9241 0.9112 0.8993 0.8884 0.8783 0.8692 0.8606 0.8452 ...... ...... ...... ...... ...... ......

1.0001 0.9778 0.9591 0.9424 0.9277 0.9147 0.9028 0.8919 0.8818 0.8725 0.8639 0.8481 0.8340 ...... ...... ...... ...... ......

1.0016 0.9804 0.9619 0.9456 0.9312 0.9183 0.9065 0.8956 0.8855 0.8762 0.8675 0.8517 0.8374 0.8244 0.8128 0.8027 ...... ......

1.0076 0.9867 0.9689 0.9529 0.9386 0.9257 0.9139 0.9030 0.8931 0.8838 0.8752 0.8595 0.8456 0.8330 0.8219 0.8119 0.8023 0.7931

1.0168 0.9967 0.9780 0.9617 0.9472 0.9343 0.9225 0.9115 0.9012 0.8919 0.8832 0.8674 0.8534 0.8408 0.8297 0.8196 0.8101 0.8009

1.0287 1.0071 0.9884 0.9717 0.9568 0.9437 0.9315 0.9203 0.9097 0.9001 0.8913 0.8752 0.8610 0.8483 0.8371 0.8268 0.8172 0.8080

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TABLE 5.28 Mass of Water Vapor in Saturated Air The values in the table are grams of water contained in a cubic meter (m3) of saturated air at a total pressure 101 325 Pa (1 atm). ⬚C

g · m⫺3

⬚C

g · m⫺3

⬚C

g · m⫺3

⫺30 ⫺29 ⫺28 ⫺27 ⫺26 ⫺25 ⫺24 ⫺23 ⫺22 ⫺21 ⫺20 ⫺19 ⫺18 ⫺17 ⫺16 ⫺15 ⫺14 ⫺13 ⫺12 ⫺11 ⫺10 ⫺9 ⫺8 ⫺7 ⫺6 ⫺5 ⫺4 ⫺3 ⫺2 ⫺1 0 1 2 3 4 5 6 7 8 9 10 11

0.341 0.375 0.413 0.456 0.504 0.554 0.607 0.667 0.733 0.804 0.883 0.968 1.063 1.164 1.273 1.375 1.510 1.650 1.800 1.965 2.140 2.331 2.539 2.761 3.003 3.250 3.512 3.810 4.131 4.473 4.849 5.199 5.569 5.947 6.35 6.80 7.25 7.75 8.25 8.80 9.40 10.00

12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52

10.65 11.35 12.05 12.80 13.60 14.45 15.35 16.30 17.30 18.35 19.40 20.55 21.75 23.05 24.35 25.75 27.20 28.75 30.35 32.05 33.80 35.60 37.55 39.55 41.65 43.90 46.20 48.60 51.21 53.86 56.61 59.51 62.53 65.52 68.61 72.00 75.56 79.24 83.05 87.04 91.22

53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93

95.56 100.0 104.5 109.1 114.1 119.2 124.7 130.2 136.0 142.1 148.4 154.9 161.3 167.9 175.1 182.6 190.3 198.2 206.5 215.1 223.7 233.0 242.0 251.2 261.1 271.6 282.3 293.4 304.8 316.6 328.7 341.2 353.6 366.2 379.9 394.1 408.6 423.5 439.0 454.8 471.2

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TABLE 5.29 Van der Waals’ Constants for Gases The van der Waals’ equation of state for a real gas is:

冉

P⫹

n 2a V2

冊

(V ⫺ nb) ⫽ nRT

for n moles

where P is the pressure, V the volume (in liters per mole ⫽ 0.001 m3 per mole in the SI system), T the temperature (in degrees Kelvin), n the amount of substance (in moles), and R the gas constant. To use the values of a and b in the table, P must be expressed in the same units as in the gas constant. Thus, the pressure of a standard atmosphere may be expressed in the SI system as follows: 1 atm ⫽ 101,325 N · m⫺2 ⫽ 101,325 Pa ⫽ 1.01325 bar The appropriate value for the gas constant is: 0.083 144 1 L · bar · K⫺1 · mol⫺1

or

0.082 056 L · atm · K⫺1 · mol⫺1

The van der Waals’ constants are related to the critical temperature and pressure, tc and Pc , in Table 6.5 by: a⫽

27 R 2 T c2 64 Pc

Substance Acetaldehyde Acetic acid Acetic anhydride Acetone Acetonitrile Acetyl chloride Acetylene Acrylic acid Acrylonitrile Allene Allyl alcohol Aluminum trichloride 2-Aminoethanol Ammonia Ammonium chloride Aniline Antimony tribromide Argon Arsenic trichloride Arsine Benzaldehyde Benzene Benzonitrile Benzyl alcohol Biphenyl Bismuth trichloride Boron trichloride Boron trifluoride Bromine (Br2) Bromobenzene Bromochlorodifluoromethane Bromoethane Bromomethane Bromotrifluoromethane

and

b⫽

RTc 8 Pc

a, L2 · bar · mol⫺2

b, L · mol⫺1

11.37 17.71 26.8 16.02 17.89 12.80 4.516 19.45 18.37 8.235 15.17 42.63 7.616 4.225 2.380 29.14 42.08 1.355 17.23 6.327 30.30 18.82 33.89 34.7 47.16 33.89 15.60 3.98 9.75 28.96 12.79 11.89 6.753 8.502

0.08695 0.1065 0.157 0.1124 0.1169 0.08979 0.05218 0.1127 0.1222 0.07467 0.1036 0.2450 0.0431 0.03713 0.00734 0.1486 0.1658 0.03201 0.1039 0.06048 0.1553 0.1193 0.1727 0.173 0.2130 0.1025 0.1222 0.05443 0.0591 0.1541 0.1055 0.08406 0.05390 0.0891

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance

a, L2 · bar · mol⫺2

b, L · mol⫺1

1,2-Butadiene 1,3-Butadiene Butanal Butane Butanenitrile Butanoic acid 1-Butanol 2-Butanol 2-Butanone 1-Butene cis-2-Butene trans-2-Butene 3-Butenenitrile Butyl acetate 1-Butylamine sec-Butylamine tert-Butylamine Butylbenzene sec-Butylbenzene tert-Butylbenzene Butyl benzoate Butylcyclohexane sec-Butylcyclohexane tert-Butylcyclohexane Butyl ethyl ether 2-Butylhexadecafluorotetrahydrofuran 1-Butyne 2-Butyne Carbon dioxide Carbon disulfide Carbon monoxide Carbon oxysulfide (COS) Carbon tetrachloride Carbon tetrafluoride Carbonyl chloride Carbonyl sulfide Chlorine Chlorine pentafluoride Chlorobenzene 1-Chlorobutane 2-Chlorobutane 1-Chloro-1,1-difluoroethane 2-Chloro-1,1-difluoroethylene Chloroethane Chloroform Chloromethane 2-Chloro-2-methylpropane Chloropentafluoroacetone Chloropentafluorobenzene Chloropentafluoroethane 1-Chloropropane 2-Chloropropane Chlorotrifluoromethane

12.76 12.17 19.48 13.93 25.76 28.18 20.90 20.94 19.97 12.76 12.58 12.58 25.76 31.22 19.41 18.37 17.78 44.071 43.74 42.77 57.97 41.19 48.89 48.34 27.05 45.41 13.31 13.68 3.658 11.25 1.472 6.975 20.01 4.029 10.65 3.933 6.343 9.581 25.80 23.22 20.01 11.91 10.49 11.7 15.34 7.566 18.98 17.08 29.53 11.27 16.11 14.53 6.873

0.1025 0.1020 0.1292 0.1168 0.1568 0.1609 0.1323 0.1326 0.1326 0.1084 0.1066 0.1066 0.1568 0.1919 0.1301 0.1273 0.1310 0.2378 0.2347 0.2310 0.2857 0.2201 0.2604 0.2614 0.1815 0.3235 0.1023 0.0998 0.04284 0.07262 0.03948 0.06628 0.1281 0.06319 0.08340 0.05817 0.05422 0.08214 0.1454 0.1527 0.1370 0.1035 0.09335 0.090 0.1019 0.06477 0.1334 0.1482 0.1843 0.1137 0.1141 0.1068 0.08110

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance Chlorotrifluorosilane Chlorotrimethylsilane m-Cresol o-Cresol p-Cresol Cyanogen Cyclobutane Cycloheptane Cyclohexane Cyclohexanol Cyclohexanone Cyclohexene Cyclopentane Cyclopentanone Cyclopentene Cyclopropane p-Cymene Decane Decanenitrile 1-Decanol 1-Decene Deuterium (normal) Deuterium oxide Diborane (B2H6) Dibromodifluoromethane 1,2-Dibromoethane 1,2-Dibromotetrafluoroethane Dibutylamine Dibutyl ether Dibutyl sulfide 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene Dichlorodifluoromethane Dichlorodifluorosilane 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene trans-1,2-Dichloroethylene Dichlorofluoromethane Dichloromethane 1,2-Dichloropropane Dichlorosilane 1,1-Dichlorotetrafluoroethane 1,2-Dichlorotetrafluoroethane Dideuterium oxide Diethanolamine Diethylamine 1,4-Diethylbenzene Diethylene glycol Diethyl ether 3,3-Diethylhexane 3,4-Diethylhexane

top of rh base of rh

a, L2 · bar · mol⫺2

b, L · mol⫺1

7.994 22.58 31.86 28.33 28.11 7.803 12.39 27.20 21.95 28.93 31.1 75.04 16.94 75.84 15.61 8.293 43.65 52.88 34.71 57.45 49.96 0.2583 5.584 6.048 15.69 13.98 20.45 34.61 33.06 49.3 34.59 35.44 34.64 10.45 11.34 15.73 17.0 13.74 13.63 11.48 12.44 21.62 12.59 15.49 15.72 5.535 45.61 19.40 45.03 29.02 17.46 47.69 47.93

0.09240 0.1617 0.1609 0.1447 0.1422 0.06952 0.0960 0.1645 0.1413 0.1586 0.170 0.1339 0.1180 0.1211 0.1097 0.07420 0.2386 0.3051 0.1988 0.2971 0.2888 0.02397 0.03090 0.07437 0.1186 0.08664 0.1494 0.2030 0.2017 0.2702 0.1767 0.1846 0.1802 0.09672 0.1095 0.1072 0.108 0.09893 0.09573 0.09060 0.08689 0.1335 0.09992 0.1318 0.1338 0.03062 0.2273 0.1383 0.2439 0.1519 0.1333 0.2707 0.2760

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance 3,3-Diethyl-2-methylpentane 3,3-Diethylpentane Diethyl sulfide Difluoroamine cis-Difluorodiazine trans-Difluorodiazine 1,1-Difluoroethane 1,1-Difluoroethylene Difluoromethane Dihexyl ether Dihydrogen disulfide Diisopropyl ether Dimethoxyethane Dimethoxymethane N,N-Dimethoxyacetamide Dimethylamine N,N-Dimethylaniline 2,2-Dimethylbutane 2,3-Dimethylbutane 2,3-Dimethyl-1-butene 3,3-Dimethyl-1-butene 2,3-Dimethyl-2-butene 1,1-Dimethylcyclohexane cis-1,2-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane cis-1,3-Dimethylcyclohexane trans-1,3-Dimethylcyclohexane cis-1,4-Dimethylcyclohexane trans-1,4-Dimethylcyclohexane 1,1-Dimethylcyclopentane cis-1,2-Dimethylcyclopentane trans-1,2-Dimethylcyclopentane Dimethyl ether N,N-Dimethylformamide 2,2-Dimethylheptane 2,2-Dimethylhexane 2,3-Dimethylhexane 2,4-Dimethylhexane 2,5-Dimethylhexane 3,3-Dimethylhexane 3,4-Dimethylhexane 1,1-Dimethylhydrazine 2,4-Dimethyl-3-isopentane Dimethyl oxalate 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane 2,3-Dimethylphenol 2,4-Dimethylphenol 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol

a, L2 · bar · mol⫺2

b, L · mol⫺1

47.20 40.64 22.85 5.028 3.043 3.539 9.691 6.000 6.184 69.17 16.15 25.26 21.65 17.28 30.19 10.44 37.92 22.55 23.29 22.59 21.55 23.83 34.30 36.44 34.89 34.30 35.11 35.47 34.54 25.37 27.04 25.67 8.690 23.57 41.29 34.87 35.24 34.97 35.49 34.72 35.06 14.69 47.05 28.97 28.49 28.96 28.79 28.48 31.35 33.49 29.99 33.64 31.32

0.2629 0.2374 0.1462 0.04446 0.03987 0.04851 0.08931 0.07058 0.06268 0.3752 0.1006 0.1836 0.1439 0.1195 0.1689 0.08510 0.1967 0.1644 0.1660 0.2566 0.1567 0.1621 0.2068 0.2143 0.2086 0.2068 0.2093 0.2114 0.2086 0.1653 0.1706 0.1663 0.07742 0.1293 0.2551 0.2260 0.2228 0.2251 0.2299 0.2201 0.2196 0.1001 0.2729 0.1644 0.1951 0.1921 0.1974 0.1892 0.1545 0.1687 0.1512 0.1710 0.1529

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance 3,5-Dimethylphenol 2,2-Dimethylpropane 2,3-Dimethylpropane 2,2-Dimethyl-1-propanol Dimethyl sulfide N,N-Dimethyl-1,2-toluidine 1,4-Dioxane Diphenyl ether Diphenylmethane Dipropylamine Dipropyl ether Dodecafluorocyclohexane Dodecafluoropentane Dodecane 1-Dodecanol 1-Dodecene Ethane 1,2-Ethanediamine Ethanethiol Ethanol Ethoxybenzene Ethyl acetate Ethyl acrylate Ethylamine Ethylbenzene Ethyl benzoate Ethyl butanoate Ethylcyclohexane Ethylcyclopentane 3-Ethyl-2,2-dimethylhexane 4-Ethyl-2,2-dimethylhexane 3-Ethyl-2,3-dimethylhexane 4-Ethyl-2,3-dimethylhexane 3-Ethyl-2,4-dimethylhexane 4-Ethyl-2,4-dimethylhexane 3-Ethyl-2,5-dimethylhexane 3-Ethyl-3,4-dimethylhexane Ethylene Ethylene glycol dimethyl ether Ethylene glycol ethyl ether acetate Ethylene oxide Ethyl formate 3-Ethylhexane Ethyl mercaptan 2-Ethyl-1-methylbenzene 3-Ethyl-1-methylbenzene 4-Ethyl-1-methylbenzene 1-Ethyl-1-methylcyclopentane Ethyl methyl ether 3-Ethyl-2-methylheptane Ethyl methyl ketone 3-Ethyl-2-methylpentane 3-Ethyl-2-methylpentane

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a, L2 · bar · mol⫺2

b, L · mol⫺1

40.92 17.17 23.13 22.25 13.34 41.71 19.29 54.61 60.46 24.82 27.12 25.09 25.58 69.14 72.69 68.17 5.570 16.30 13.23 12.56 35.70 20.57 23.70 10.79 30.86 43.73 30.53 35.70 27.90 47.24 46.45 47.35 47.49 47.31 45.52 47.42 47.00 4.612 21.65 33.97 8.922 15.91 35.76 11.24 40.66 41.67 40.63 34.18 12.70 48.81 20.13 34.74 34.53

0.2037 0.1410 0.1669 0.1444 0.09453 0.2225 0.1171 0.2538 0.2798 0.1591 0.1821 0.1955 0.2161 0.3741 0.3598 0.3694 0.06499 0.09796 0.09447 0.08710 0.1996 0.1401 0.1530 0.08433 0.1782 0.2236 0.1922 0.2089 0.1746 0.2752 0.2784 0.2692 0.2742 0.2736 0.2613 0.2800 0.2682 0.05821 0.1439 0.05594 0.06779 0.1115 0.2253 0.08098 0.2226 0.2331 0.2262 0.2058 0.1034 0.2847 0.1340 0.2183 0.2134

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance Ethyl 2-methylpropanoate Ethyl methyl sulfide 3-Ethylpentane Ethyl phenyl ether Ethyl propanoate Ethyl propyl ether m-Ethyltoluene o-Ethyltoluene p-Ethyltoluene Ethyl vinyl ether Fluorine Fluorobenzene Fluoroethane Fluoroethylene Fluoromethane Formaldehyde Furan 2-Furaldehyde (furfural) Germanium tetrachloride Germanium tetrahydride Glycerol Hafnium tetrachloride Helium (equilibrium) Heptane 1-Heptanol 2-Heptanol 2-Heptanone 1-Heptene Hexadecafluoroheptane 1,5-Hexadiene Hexafluoraoacetone Hexafluorobenzene Hexane Hexanenitrile Hexanoic acid 1-Hexanol 2-Hexanol 3-Hexanol 2-Hexanone 3-Hexanone 1-Hexene cis-2-Hexene trans-2-Hexene cis-3-Hexene trans-3-Hexene Hexylcyclopentane Hydrazine Hydrogen (normal) Hydrogen bromide Hydrogen chloride Hydrogen cyanide Hydrogen deuteride Hydrogen fluoride

a, L2 · bar · mol⫺2

b, L · mol⫺1

29.05 19.45 29.49 35.16 25.86 22.45 41.73 40.67 40.63 16.17 1.171 20.10 8.170 5.984 5.009 7.356 12.74 22.23 23.12 5.743 22.98 26.01 0.0346 30.89 37.22 35.72 31.78 28.82 40.58 21.79 12.66 26.63 24.97 35.50 39.94 31.35 30.25 29.44 30.27 29.84 23.12 23.86 23.75 23.77 24.25 59.38 8.46 0.2484 4.500 3.700 11.29 0.2527 9.565

0.1872 0.1300 0.1944 0.1963 0.1688 0.1600 0.2334 0.2226 0.2262 0.1213 0.02896 0.1279 0.07758 0.06504 0.05617 0.06425 0.0926 0.1182 0.1489 0.06555 0.07037 0.1282 0.02356 0.2038 0.2097 0.2093 0.1850 0.09400 0.3046 0.1532 0.1264 0.1641 0.1753 0.1996 0.2150 0.1829 0.1840 0.1803 0.1837 0.1824 0.1634 0.1641 0.1640 0.1638 0.1663 0.3206 0.0462 0.02651 0.04415 0.04061 0.08806 0.02516 0.0739

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance Hydrogen iodide Hydrogen selenide Hydrogen sulfide Indane Iodobenzene Iodomethane Isobutyl acetate Isobutylamine Isobutylbenzene Isobutylcyclohexane Isobutyl formate Isopropylamine Isopropylbenzene Isopropylcyclohexane Isopropylcyclopentane 4-Isopropylheptane 2-Isopropyl-1-methylbenzene 3-Isopropyl-1-methylbenzene 4-Isopropyl-1-methylbenzene 3-Isopropyl-2-methylhexane Ketene Krypton Mercury Methane Methanethiol Methanol Methoxybenzoate Methyl acetate Methyl acrylate Methylamine 2-Methyl-1,3-butadiene 3-Methyl-1,3-butadiene 2-Methylbutane Methyl butanoate 3-Methylbutanoic acid 2-Methyl-1-butanol 3-Methyl-1-butanol 2-Methyl-2-butanol 3-Methyl-2-butanol 3-Methyl-2-butanone 2-Methyl-1-butene 3-Methyl-1-butene 2-Methyl-2-butene Methylcyclohexane Methylcyclopentane N-Methylethylamine Methyl formate 2-Methylfuran 2-Methylheptane 3-Methylheptane 4-Methylheptane 2-Methylhexane 3-Methylhexane

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a, L2 · bar · mol⫺2

b, L · mol⫺1

6.309 5.523 4.544 34.63 33.54 12.34 29.05 19.30 40.40 40.39 22.82 14.30 36.20 42.06 35.11 48.28 45.14 44.00 43.94 50.93 19.1 2.325 5.193 2.300 8.911 9.472 28.60 15.75 19.67 7.106 17.74 17.46 18.29 25.83 33.94 24.51 24.72 23.24 23.30 23.20 16.9 18.08 17.26 27.51 21.87 19.39 11.54 14.67 36.78 36.40 36.21 30.01 29.70

0.05303 0.0479 0.04339 0.1802 0.1658 0.08327 0.1845 0.1325 0.2215 0.2195 0.1476 0.1080 0.2044 0.2342 0.2082 0.2832 0.2401 0.2354 0.2398 0.2870 0.1044 0.0396 0.01057 0.04301 0.06756 0.06584 0.1579 0.1108 0.1308 0.05879 0.1307 0.1245 0.1415 0.1661 0.1923 0.1518 0.1526 0.1523 0.1493 0.1494 0.129 0.1405 0.1279 0.1713 0.1463 0.1391 0.08406 0.1160 0.2342 0.2301 0.2297 0.2016 0.1977

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance Methylhydrazine Methyl isobutanoate Methyl isocyanate 1-Methyl-2-isopropylbenzene 1-Methyl-4-isopropylbenzene Methyl 2-methylpropanoate 2-Methyloctane 2-Methylpentane 3-Methylpentane 2-Methyl-2,4-pentanediol Methyl pentanoate 2-Methyl-3-pentanol 3-Methyl-3-pentanol 4-Methyl-2-pentanol 4-Methyl-2-pentanone 2-Methyl-2-pentene cis-3-Methyl-2-pentene trans-3-Methyl-2-pentene cis-4-Methyl-2-pentene trans-4-Methyl-2-pentene 2-Methylpropanal 2-Methyl-1-propanamine 2-Methylpropane (isobutane) Methyl propanoate 2-Methylpropanoic acid 2-Methyl-1-propanol 2-Methyl-2-propanol 2-Methylpropene 2-Methylpropyl acetate 2-Methylpropyl formate 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 1-Methylstyrene 2-Methyltetrahydrofuran 2-Methylthiophene 3-Methylthiophene Methyl vinyl ether Morpholine Naphthalene Neon Niobium pentafluoride Nitric oxide (NO) Nitroethane Nitrogen-14 Nitrogen chloride difluoride Nitrogen dioxide (NO2) Nitrogen trifluoride Nitrous oxide (N2O) Nitromethane Nitrosyl chloride Nonane 1-Nonanol

a, L2 · bar · mol⫺2

b, L · mol⫺1

11.67 24.87 12.6 42.7 45.27 24.50 43.50 23.83 23.75 39.05 29.39 27.96 27.45 22.38 29.08 23.86 23.86 24.60 23.03 23.32 18.49 19.30 13.36 20.51 28.9 20.35 18.81 12.73 29.05 22.54 24.45 27.08 25.89 36.69 22.37 22.10 21.98 11.65 20.36 40.32 0.208 25.22 1.46 24.13 15.18 6.447 5.36 3.58 3.852 17.18 6.191 45.11 50.00

0.07334 0.1639 0.09161 0.234 0.2478 0.163 7 0.2641 0.1707 0.1677 0.2054 0.1847 0.1730 0.1699 0.1388 0.1815 0.1641 0.1641 0.1656 0.1675 0.1685 0.1285 0.1325 0.1168 0.1377 0.170 0.1324 0.1324 0.1086 0.1845 0.1476 0.1403 0.1496 0.1428 0.1999 0.1484 0.1299 0.1282 0.09520 0.1174 0.1920 0.01709 0.1220 0.0289 0.1544 0.1288 0.06089 0.0443 0.05364 0.04435 0.1041 0.05014 0.2702 0.2634

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance 1-Nonene Octadecafluorooctane Octafluorocyclobutane Octafluoropropane Octamethylcyclotetrasiloxane Octane 1-Octanol 2-Octanol 1-Octene cis-2-Octene Osmium tetraoxide Oxygen Oxygen difluoride Ozone Pentadecane 1-Pentadecene 1,2-Pentadiene cis-1,3-Pentadiene 1,4-Pentadiene Pentafluorobenzene 2,2,3,3,4-Pentamethylpentane 2,2,3,4,4-Pentamethylpentane Pentanal Pentane Pentanenitrile Pentanoic acid 1-Pentanol 2-Pentanol 2-Pentanone 3-Pentanone 1-Pentene cis-2-Pentene trans-2-Pentene Pentylbenzene Pentyl formate 1-Pentyne Perchloryl fluoride (ClO3F) Phenol Phosgene Phosphine Phosphonium chloride Phosphorus Phosphorus chloride difluoride Phosphorus dichloride fluoride Phosphorus trifluoride Phosphoryl chloride difluoride Phosphoryl trifluoride Piperidine Propadiene Propanal Propane 1,2-Propanediol 1,3-Propanediol

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a, L2 · bar · mol⫺2

b, L · mol⫺1

43.68 44.27 15.81 12.96 75.30 37.86 44.71 41.98 35.01 35.42 2.79 1.382 2.726 3.570 95.91 99.00 18.13 17.98 17.58 23.45 46.85 47.82 25.21 19.13 34.16 33.68 25.81 24.89 24.85 24.65 17.86 17.83 18.30 51.85 27.97 17.53 7.371 22.93 10.65 4.693 4.111 53.6 8.47 12.50 4.954 11.90 8.26 20.84 8.23 14.08 9.385 18.74 21.11

0.2629 0.3143 0.1450 0.1338 0.4579 0.2370 0.2371 0.2376 0.2227 0.2176 0.2447 0.03186 0.04516 0.04977 0.4834 0.5011 0.1284 0.1292 0.1311 0.1571 0.2593 0.2716 0.1622 0.1449 0.1772 0.1867 0.1572 0.1585 0.1578 0.1565 0.1370 0.1338 0.1391 0.2718 0.1730 0.1266 0.07130 0.1177 0.08340 0.05155 0.04545 0.157 0.0833 0.0962 0.06510 0.1001 0.0849 0.1250 0.0747 0.0995 0.09044 0.1068 0.1143

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance Propanenitrile Propanoic acid 1-Propanol 2-Propanol 2-Propenal Propene Propyl acetate Propylamine Propylbenzene Propylcyclopentane Propylcyclohexane Propylene oxide Propyl formate Propyne Pyridine Pyrrole Pyrrolidine Quinoline Radon Selenium Silicon chloride trifluoride Silicon tetrachloride Silicon tetrafluoride Silicon tetrahydride (silane) Styrene Sulfur (S) Sulfur dioxide Sulfur hexafluoride (SF6) Sulfur trioxide 1,1,2,2-Tetrachlorodifluoroethane Tetrachloroethylene Tetrachloromethane Tetradecafluorohexane Tetradecafluoromethylcyclohexane 1-Tetradecanol Tetraethylsilane Tetrafluoroethylene Tetrafluorohydrazine (N2F4) Tetrafluoromethane Tetrahydrofuran Tetrahydropyran 1,2,4,5-Tetramethylbenzene 2,2,3,3-Tetramethylbutane 2,2,3,3-Tetramethylhexane 2,2,3,4-Tetramethylhexane 2,2,3,5-Tetramethylhexane 2,2,4,4-Tetramethylhexane 2,2,4,5-Tetramethylhexane 2,2,5,5-Tetramethylhexane 2,3,3,4-Tetramethylhexane 2,3,3,5-Tetramethylhexane 2,3,4,4-Tetramethylhexane 2,3,4,5-Tetramethylhexane

a, L2 · bar · mol⫺2

b, L · mol⫺1

21.57 23.49 16.26 15.82 14.44 8.411 26.23 15.26 37.14 38.80 38.59 13.78 20.79 8.40 19.77 18.82 16.84 36.70 6.601 33.4 7.95 20.96 5.259 4.30 32.15 24.3 6.714 7.857 8.57 25.74 24.98 20.01 30.75 29.66 89.91 40.85 6.954 7.426 4.040 16.39 20.02 45.8 32.76 45.11 47.36 46.45 48.26 47.05 45.03 47.13 46.79 47.32 46.86

0.1369 0.1386 0.1080 0.1109 0.1017 0.08211 0.1700 0.1095 0.2073 0.2189 0.2255 0.1019 0.1377 0.0744 0.1136 0.1049 0.1056 0.1672 0.06239 0.0675 0.0921 0.1470 0.072361 0.0579 0.1799 0.0660 0.05636 0.08786 0.0622 0.1665 0.1435 0.1281 0.2448 0.2171 0.4289 0.2411 0.08085 0.08564 0.06325 0.1082 0.1247 0.2422 0.2056 0.2580 0.2721 0.2753 0.2819 0.2802 0.2760 0.2653 0.2733 0.2691 0.2723

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance 3,3,4,4-Tetramethylhexane 2,2,3,3-Tetramethylpentane 2,2,3,4-Tetramethylpentane 2,2,4,4-Tetramethylpentane 2,3,3,4-Tetramethylpentane Tetramethylsilane Thiophene Tin(IV) chloride Titanium(IV) chloride Toluene 1,2-Toluidine 1,3-Toluidine 1,4-Toluidine Tributoxyborane Tributylamine 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane Trichlorofluorosilane Trichloromethane Trichloromethylsilane 1,2,3-Trichloropropane 1,1,2-Trichlorotrifluoroethane 1,2,2-Trichlorotrifluoroethane Tridecane 1-Tridecanol 1-Tridecene Tridecylcyclopentane Triethanolamine Triethylamine Trifluoroacetic acid 1,1,1-Trifluoroethane Trifluoromethane Trimethylamine 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene 2,2,3-Trimethylbutane 2,2,3-Trimethyl-1-butene 1,1,2-Trimethylcyclopentane 1,1,3-Trimethylcyclopentane 2,2,3-Trimethylheptane 2,2,4-Trimethylheptane 2,3,4-Trimethylheptane 3,3,4-Trimethylheptane 2,2,3-Trimethylhexane 2,2,4-Trimethylhexane 2,2,5-Trimethylhexane 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane 2,3,4-Trimethylpentane

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a, L2 · bar · mol⫺2

b, L · mol⫺1

47.46 39.29 39.37 38.76 39.65 20.81 17.21 27.25 25.47 24.89 33.36 34.06 31.74 81.34 65.31 20.14 25.47 17.21 14.68 15.67 15.34 23.77 31.29 20.25 20.25 79.09 81.20 77.93 139.6 32.14 27.59 21.61 9.302 5.378 13.37 37.28 38.03 37.87 27.86 28.57 33.31 33.42 48.07 47.49 47.96 47.68 40.5 40.50 40.38 33.92 33.61 34.03 34.28

0.2615 0.2304 0.2367 0.2403 0.2325 0.1653 0.1058 0.1641 0.1423 0.1499 0.1681 0.1717 0.1602 0.3891 0.3645 0.1317 0.1508 0.1127 0.1111 0.1277 0.1019 0.1638 0.1713 0.1481 0.1481 0.4176 0.3942 0.4121 0.6536 0.3340 0.1836 0.1567 0.09572 0.06403 0.1101 0.1999 0.2088 0.2118 0.1869 0.1910 0.2048 0.2091 0.2801 0.2847 0.2785 0.2730 0.2452 0.2516 0.2533 0.2145 0.2202 0.2114 0.2157

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TABLE 5.29 Van der Waals’ Constants for Gases (Continued) Substance 2,2,4-Trimethyl-1,3-pentanediol Tungsten(VI) fluoride (WF6) Undecane 1-Undecene Uranium(VI) fluoride (UF6) Vinyl acetate Vinyl chloride Vinyl fluoride Vinyl formate Xenon Xenon difluoride Xenon tetrafluoride m-Xylene o-Xylene p-Xylene Water Zirconium(IV) chloride

a, L2 · bar · mol⫺2

b, L · mol⫺1

19.96 13.25 60.88 59.17 16.01 32.31 9.62 5.98 11.38 4.192 12.46 15.52 31.41 31.06 31.54 5.537 30.59

0.2692 0.1063 0.3396 0.3310 0.1128 0.2296 0.07975 0.06502 0.08541 0.05156 0.7037 0.09035 0.1814 0.1756 0.1824 0.03052 0.1401

TABLE 5.30 Triple Points of Various Materials Substance

Triple point, K

Ammonia Argon Boron tribromide Bromine Carbon dioxide Cyclopropane Deuterium oxide 1-Hexene Hydrogen, normal Hydrogen, para Hydrogen bromide Hydrogen chloride Iodine heptafluoride Krypton Methane Methane-d1 Methane-d2 Methane-d3 Methane-d4 Molybdenum oxide tetrafluoride Molybdenum pentafluoride Neon Neptunium hexafluoride Niobium pentabromide Niobium pentachloride Nitrogen 1-Octene Oxygen

195.46 83.78 226.67 280.4 216.65 145.59 276.97 133.39 13.95 13.81 186.1 158.8 279.6 115.95 90.67 90.40 90.14 89.94 89.79 370.3 340 24.55 328.25 540.6 476.5 63.15 171.45 54.34

Pressure, mmHg 45.58 516 44.1

54 ⬃232

548 87.60 84.52 81.80 80.12 79.13

324 758.0

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TABLE 5.30 Triple Points of Various Materials (Continued) Substance

Triple point, K

Phosphorus, white Plutonium hexafluoride Propene Radon Rhenium dioxide trifluoride Rhenium heptafluoride Rhenium oxide pentafluoride Rhenium pentafluoride Succinonitrile (NIST standard) Sulfur dioxide Tantalum pentabromide Tantalum pentachloride Tungsten oxide tetrafluoride Uranium hexafluoride Water Xenon

5.9.1

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Pressure, mmHg

863 324.74 103.95 202 363 321.4 313.9 321 331.23 197.68 553 489.0 377.8 337.20 273.16 161.37

32 760 533.0 ⬃500

1.256

1 139.6 612

Some Physical Chemistry Equations for Gases

A number of physical chemistry relationships, not enumerated in other sections (see Index), will be discussed in this section. Boyle’s law states that the volume of a given quantity of a gas varies inversely as the pressure, the temperature remaining constant. That is, V⫽

constant P

or

PV ⫽ constant

A convenient form of the law, true strictly for ideal gases, is P1V1 ⫽ P2V2 Charles’ law, also known as Gay-Lussac’s law, states that the volume of a given mass of gas varies directly as the absolute temperature if the pressure remains constant, that is, V ⫽ constant T Combining the laws of Boyle and Charles into one expression gives P1V1 P2V2 ⫽ T1 T2 In terms of moles, Avogadro’s hypothesis can be stated: The same volume is occupied by one mole of any gas at a given temperature and pressure. The number of molecules in one mole is known as the Avogadro number constant NA . The behavior of all gases that obey the laws of Boyle and Charles, and Avogadro’s hypothesis, can be expressed by the ideal gas equation: PV ⫽ nRT

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where R is called the gas constant and n is the number of moles of gas. If pressure is written as force per unit area and the volume as area times length, then R has the dimensions of energy per degree per mole— 8.314 J · K⫺1 · mol⫺1 or 1.987 cal · K⫺1 · mol⫺1. Dalton’s law of partial pressures states that the total pressure exerted by a mixture of gases is equal to the sum of the pressures which each component would exert if placed separately into the container:

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Ptotal ⫽ p1 ⫹ p2 ⫹ p3 ⫹ · · · There are two ways to express the fraction which one gaseous component contributes to the total mixture: (1) the pressure fraction, pi /Ptotal , and (2) the mole fraction, ni /n total . 5.9.1.1

Equations of State (PVT Relations for Real Gases)

1. Virial equation represents the experimental compressibility of a gas by an empirical equation of state: PV ⫽ Ap ⫹ Bp P ⫹ Cp P2 ⫹ · · · or Cv ⫹ ··· V2

PV ⫽ Av ⫹ BvV ⫹

where A, B, C, . . . are called the virial coefficients and are a function of the nature of the gas and the temperature. 2. Van der Waals’ equation:

冉

P⫹

an 2 V2

冊

(V ⫺ nb) ⫽ nRT

where the term an 2/V 2 is the correction for intermolecular attraction among the gas molecules and the nb term is the correction for the volume occupied by the gas molecules. The constants a and b must be fitted for each gas from experimental data (Table 5.28); consequently the equation is semiempirical. The constants are related to the critical-point constants (Table 6.5) as follows: a ⫽ 3PcV 2 b⫽

Vc 3

R⫽

8PcVc 3Tc

Substitution into van der Waals’ equation and rearrangement leads to only the terms P/Pc , V/Vc , and T/Tc , which are called the reduced variables PR , VR , and TR . For 1 mole of gas,

冉

PR ⫹

3 V R2

冊冉

VR ⫺

1 3

冊

⫽

8 T 3 R

3. Berthelot’s equation of state, used by many thermodynamicists, is PV ⫽ nRT

冋

1⫹

9 PTc 128 Pc T

冉

1⫺6

T 2c T2

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This equation requires only knowledge of the critical temperature and pressure for its use and gives accurate results in the vicinity of room temperature for unassociated substances at moderate pressures.

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5.9.1.2 Properties of Gas Molecules Vapor Density. Substitution of the Antoine vapor-pressure equation for its equivalent log P in the ideal gas equation gives log ␳vap ⫽ log M ⫺ log R ⫺ log (t ⫹ 273.15) ⫹ A ⫺

B t⫹C

where ␳vap is the vapor density in g· mL⫺1 at t⬚C, M is the molecular weight, R is the gas constant, and A, B, and C are the constants of the Antoine equation for vapor pressure. Since this equation is based on the ideal gas law, it is accurate only at temperatures at which the vapor of any specific compound follows this law. This condition prevails at reduced temperatures (TR) of about 0.5 K. Velocities of Molecules. The mean square velocity of gas molecules is given by u2 ⫽

3kT 3RT ⫽ m M

where k is Boltzmann’s constant and m is the mass of the molecule. The mean velocity is given by u⫽

冉 冊 8u2 3␲

1/2

Viscosity. On the assumption that molecules interact like hard spheres, the viscosity of a gas is

␩⫽

冉 冊冉 冊 5 16␴2

mkT ␲

1/2

where ␴ is the molecular diameter. Mean Free Path. The mean free path of a gas molecule l and the mean time between collisions ␶ are given by l⫽

␶⫽

m

␲␳␴2p 2 1 4␩ ⫽ u 5P

Graham’s Law of Diffusion. The rates at which gases diffuse under the same conditions of temperature and pressure are inversely proportional to the square roots of their densities: r1 ⫽ r2

冉冊 ␳2 ␳1

1/2

Since ␳ ⫽ MP/RT for an ideal gas, it follows that r1 ⫽ r2

冉 冊 M2 M1

1/2

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Henry’s Law. The solubility of a gas is directly proportional to the partial pressure exerted by the gas:

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pi ⫽ kxi Joule-Thompson Coefficient for Real Gases. This expresses the change in temperature with respect to change in pressure at constant enthalpy:

␮␲ ⫽

冉 冊 ⭸T ⭸P

H

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SECTION 6

THERMODYNAMIC PROPERTIES 6.1

ENTHALPIES AND GIBBS ENERGIES OF FORMATION, ENTROPIES, AND HEAT CAPACITIES 6.1.1 Some Thermodynamic Relations Table 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds Table 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds Table 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds Table 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds 6.2 CRITICAL PHENOMENA Table 6.5 Critical Properties

6.1

6.1 6.2 6.5 6.51 6.81 6.124 6.142 6.143

ENTHALPIES AND GIBBS ENERGIES OF FORMATION, ENTROPIES, AND HEAT CAPACITIES

The tables in this section contain values of the enthalpy and Gibbs energy of formation, entropy, and heat capacity at 298.15 K (25⬚C). No values are given in these tables for metal alloys or other solid solutions, for fused salts, or for substances of undefined chemical composition. The physical state of each substance is indicated in the column headed “State” as crystalline solid (c), liquid (lq), or gaseous (g). Solutions in water are listed as aqueous (aq). The values of the thermodynamic properties of the pure substances given in these tables are, for the substances in their standard states, defined as follows: For a pure solid or liquid, the standard state is the substance in the condensed phase under a pressure of 1 atm (101 325 Pa). For a gas, the standard state is the hypothetical ideal gas at unit fugacity, in which state the enthalpy is that of the real gas at the same temperature and at zero pressure. The values of ⌬f H⬚ and ⌬f G⬚ that are given in the tables represent the change in the appropriate thermodynamic quantity when one mole of the substance in its standard state is formed, isothermally at the indicated temperature, from the elements, each in its appropriate standard reference state. The standard reference state at 25⬚C for each element has been chosen to be the standard state that is thermodynamically stable at 25⬚C and 1 atm pressure. The standard reference states are indicated in the tables by the fact that the values of ⌬f H⬚ and ⌬f G⬚ are exactly zero. The values of S⬚ represent the virtual or “thermal” entropy of the substance in the standard state at 298.15 K (25⬚C), omitting contributions from nuclear spins. Isotope mixing effects are also excluded except in the case of the 1H 9 2H system. Solutions in water are designated as aqueous, and the concentration of the solution is expressed in terms of the number of moles of solvent associated with 1 mol of the solute. If no concentration is indicated, the solution is assumed to be dilute. The standard state for a solute in aqueous solution is taken as the hypothetical ideal solution of unit molality (indicated as std. state or ss). In this state 6.1

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the partial molal enthalpy and the heat capacity of the solute are the same as in the infinitely dilute real solution. For some tables the uncertainty of entries is indicated within parentheses immediately following the value; viz., an entry 34.5(4) implies 34.5⫾0.4 and an entry 34.5(12) implies 34.5⫾1.2. References: D. D. Wagman, et al., The NBS Tables of Chemical Thermodynamic Properties, in J. Phys. Chem. Ref. Data, 11: 2, l982; M. W. Chase, et al., JANAF Thermochemical Tables, 3rd ed., American Chemical Society and the American Institute of Physics, 1986 (supplements to JANAF appear in J. Phys. Chem. Ref. Data); Thermodynamic Research Center, TRC Thermodynamic Tables, Texas A&M University, College Station, Texas; I. Barin and O. Knacke, Thermochemical Properties of Inorganic Substances, Springer-Verlag, Berlin, 1973; J. B. Pedley, R. D. Naylor, and S. P. Kirby, Thermochemical Data of Organic Compounds, 2nd ed., Chapman and Hall, London, 1986; V. Majer and V. Svoboda, Enthalpies of Vaporization of Organic Compounds, International Union of Pure and Applied Chemistry, Chemical Data Series No. 32, Blackwell, Oxford, 1985.

6.1.1

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Some Thermodynamic Relations

6.1.1.1 Enthalpy of Formation. Once standard enthalpies are assigned to the elements, it is possible to determine standard enthalpies for compounds. For the reaction: C(graphite) ⫹ O2(g) : CO2(g)

⌬H⬚ ⫽ ⫺393.51 kJ

(6.1)

Since the elements are in their standard states, the enthalpy change for the reaction is equal to the standard enthalpy of CO2 less the standard enthalpies of C and O2, which are zero in each instance. Thus, ⌬f H⬚ ⫽ ⫺393.51 ⫺ 0 ⫺ 0 ⫽ ⫺393.51 kJ

(6.2)

Tables of enthalpies, such as Tables 6.1 and 6.3, can be used to determine the enthalpy for any reaction at 1 atm and 298.15 K involving the elements and any of the compounds appearing in the tables. The solution of 1 mole of HCl gas in a large amount of water (infinitely dilute real solution) is represented by: HCl(g) ⫹ inf H2O : H⫹(aq) ⫹ Cl⫺(aq)

(6.3)

The heat evolved in the reaction is ⌬H⬚ ⫽ ⫺74.84 kJ. With the value of ⌬f H⬚ from Table 6.3, one has for the reaction: ⌬f H⬚ ⫽ ⌬f H⬚[H⫹(aq)] ⫹ ⌬f H⬚[Cl⫺(aq)] ⫺ ⌬f H⬚[HCl(g)]

(6.4)

for the standard enthalpy of formation of the pair of ions H⫹ and Cl⫺ in aqueous solution (standard state, m ⫽ 1). To obtain the ⌬f H⬚ values for individual ions, the enthalpy of formation of H⫹(aq) is arbitrarily assigned the value zero at 298.15 K. Thus, from Eq. (6.4): ⌬f H⬚[Cl⫺(aq)] ⫽ ⫺74.84 ⫹ (⫺92.31) ⫽ ⫺167.15 kJ With similar data from Tables 6.1 and 6.3, the enthalpies of formation of other ions can be determined. Thus, from the ⌬f H⬚[KCl(aq, std. state, m ⫽ 1 or aq, ss)] of ⫺419.53 kJ and the foregoing value for ⌬f H⬚[Cl⫺(aq, ss)]: ⌬f H⬚[K⫹(aq, ss)] ⫽ ⌬f H⬚[KCl(aq, ss)] ⫺ ⌬f H⬚[Cl⫺(aq, ss)] ⫽ ⫺419.53 ⫺(⫺167.15) ⫽ ⫺252.38 kJ

(6.5)

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6.1.1.2 Enthalpy of Vaporization (or Sublimation) When the pressure of the vapor in equilibrium with a liquid reaches 1 atm, the liquid boils and is completely converted to vapor on absorption of the enthalpy of vaporization ⌬Hv at the normal boiling point Tb . A rough empirical relationship between the normal boiling point and the enthalpy of vaporization (Trouton’s rule) is: ⌬Hv ⫽ 88 J · mol⫺1 · K⫺1 Tb

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(6.6)

It is best applied to nonpolar liquids which form unassociated vapors. To a first approximation, the enthalpy of sublimation ⌬Hs at constant temperature is: ⌬Hs ⫽ ⌬Hm ⫹ ⌬Hv

(6.7)

where ⌬Hm is the enthalpy of melting. The Clapeyron equation expresses the dynamic equilibrium existing between the vapor and the condensed phase of a pure substance: dP ⌬Hv ⫽ dT T⌬V

(6.8)

where ⌬V is the volume increment between the vapor phase and the condensed phase. If the condensed phase is solid, the enthalpy increment is that of sublimation. Substitution of V ⫽ RT/P into the foregoing equation and rearranging gives the Clausius-Clapeyron equation, dP ⌬Hv ⫽ P dT RT 2

(6.9)

or ⌬Hv ⫽ ⫺R

d(ln P) 1/T

(6.10)

which may be used for calculating the enthalpy of vaporization of any compound provided its boiling point at any pressure is known. If an Antoine equation is available (such as Eq. (5.1), page 5.30), differentiation and insertion into the foregoing equation gives: ⌬Hv ⫽

4.5757T 2B (T ⫹ C ⫺ 273.15)2

(6.11)

Inclusion of a compressibility factor into the foregoing equation, as suggested by the Haggenmacher equation improves the estimate of ⌬Hv: ⌬Hv ⫽

RT 2 P

冉 冊冉 dP dT

1⫺

T c3 P T 3Pc

冊

1/2

(6.12)

where Tc and Pc are critical constants (Table 6.5). Although critical constants may be unknown, the compressibility factor is very nearly constant for all compounds belonging to the same family, and an estimate can be deduced from a related compound whose critical constants are available. 6.1.1.3 Heat Capacity (or Specific Heat) The temperature dependence of the heat capacity is complex. If the temperature range is restricted, the heat capacity of any phase may be represented adequately by an expression such as: Cp ⫽ a ⫹ bT ⫹ cT 2

(6.13)

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THERMODYNAMIC PROPERTIES

in which a, b, and c are empirical constants. These constants may be evaluated by taking three pieces of data: (T1, Cp,1), (T2, Cp,2), and (T3, Cp,1), and substituting in the following expressions: Cp,1 (T1 ⫺ T2 )(T1 ⫺ T3 )

⫹

Cp,2 (T2 ⫺ T1 )(T2 ⫺ T3 )

Cp,1 ⫺ Cp,2 T1 ⫺ T2

⫹

Cp,3 (T3 ⫺ T2 )(T3 ⫺ T1 )

⫽c

⫺ [(T1 ⫹ T2 )c] ⫽ b

(Cp,1 ⫺ bT1 ) ⫺ cT 21 ⫽ a

cap height base of text

(6.14)

(6.15) (6.16)

Smoothed data presented at rounded temperatures, such as are available in Tables 6.2 and 6.4, plus the Cp⬚ values at 298 K listed in Table 6.1 and 6.3, are especially suitable for substitution in the foregoing parabolic equations. The use of such a parabolic fit is appropriate for interpolation, but data extrapolated outside the original temperature range should not be sought. 6.1.1.4 Enthalpy of a System The enthalpy increment of a system over the interval of temperature from T1 to T2 , under the constraint of constant pressure, is given by the expression: H2 ⫺ H1 ⫽

冕

T2

T1

Cp dT

(6.17)

The enthalpy over a temperature range that includes phase transitions, melting, and vaporization, is represented by: H2 ⫺ H1 ⫽

冕

T2

T1

⫹

Cp(c,II) dT ⫹ ⌬Ht ⫹

冕

Tb

Tm

冕 冕

Cp(1q) dT ⫹ ⌬Hv ⫹

Tm

T1

Cp(c,I) dT ⫹ ⌬Hm

T2

Tb

Cp(g) dT

(6.18)

Integration of heat capacities, as expressed by Eq. (6.13), leads to: ⌬H ⫽ a(T2 ⫺ T1) ⫹ 6.1.1.5

b(T22 ⫺ T21) c(T32 ⫺ T31) ⫹ 2 3

(6.19)

Entropy In the physical change of state, ⌬Sm ⫽

⌬Hm Tm

(6.20)

⌬Sv ⫽

⌬Hv Tb

(6.21)

⌬Ss ⫽

⌬Hs Ts

(6.22)

is the entropy of melting (or fusion),

is the entropy of vaporization, and

is the entropy of sublimation.

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THERMODYNAMIC PROPERTIES

cap height base of text

A general expression for the entropy of a system, involving any phase transitions, is S2 ⫺ S1 ⫽

冕

Tt

Cp(c,II) dT T

T1

⫹

冕

Tb

⫹

Cp(1q) dT

Tm

T

⌬Ht ⫹ T ⫹

冕

Tm

Cp(c,I) dT T

Tb

⌬Hv ⫹ T

冕

Tm

⫹

⌬Hm T

Cp(g) dT

Tb

top of rh base of rh

(6.23)

T

If Cp is independent of temperature, ⌬S ⫽ Cp(ln T2 ⫺ ln T1 ) ⫽ 2.303 Cp log

T2 T1

(6.24)

If the heat capacities change with temperature, an empirical equation like Eq. (6.13) may be inserted in Eq. (6.23) before integration. Usually the integration is performed graphically from a plot of either Cp /T versus T or Cp versus ln T. TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds

Substance Acenaphthene Acenaphthylene Acetaldehyde Acetaldoxime Acetamide Acetamidoguanidine nitrate 1-Acetamido-2-nitroguanidine 5-Acetamidotetrazole Acetanilide Acetic acid ionized; std. state, m ⫽ 1 Acetic anhydride Acetone Acetonitrile Acetophenone Acetyl bromide Acetyl chloride Acetylene Acetylene-d2 Acetylenedicarboxylic acid Acetyl fluoride 1-Acetylimidazole Acetyl iodide Acridine Adamantane

Physical State c c lq g c lq c c c c c lq g aq lq lq g lq g lq lq lq g g g c g c lq c c

⌬f H⬚ kJ · mol⫺1 70.34 186.7 ⫺192.2 ⫺166.1 ⫺77.9 ⫺81.6 ⫺317.0 ⫺494.0 ⫺193.6 ⫺5.0 ⫺210.6 ⫺484.4 ⫺432.2 ⫺486.34 ⫺624.4 ⫺248.4 ⫺217.1 31.4 74.0 ⫺142.5 ⫺223.5 ⫺272.9 ⫺242.8 227.4 221.5 ⫺578.2 ⫺442.1 ⫺574.0 ⫺163.5 179.4 ⫺194.1

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1 188.9

Cp⬚ J · deg⫺1 · mol⫺1

160.4 263.8

190.4 166.4 89.0 55.3

115.0

91.3

⫺390.2 ⫺374.2 ⫺369.65 ⫺489.14 ⫺152.7 ⫺152.7 86.5 91.9 ⫺17.0

159.9 283.5 86.7 268.8 198.8 295.3 149.7 243.4 249.6

123.6 63.4 ⫺6.3 168.230 126.3 74.5 91.5 52.2 204.6

⫺208.2 ⫺205.8 209.0 205.9

201.0 295.1 201.0 208.9

117.0 67.8 44.1 49.3

⫺127.6 ⫺133.0

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(McGHP)

6.6

INTERACTIVE

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SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Adenine (⫹)-Alanine (⫺)-Alanine (⫾)-Alanine ␤-Alanine (⫾)-N-Alanylglycine (⫺)-Alanylglycine Allene Alloxan monohydrate Allylamine Allyl tert-butyl sulfide Allyl ethyl sulfone Allyl methyl sulfone Allyl trichloroacetate Allyl (see Propene) Aminetrimethylboron 3-Aminoacetophenone 4-Aminoacetophenone 2-Aminoacridine 9-Aminoacridine 2-Aminobenzoic acid 3-Aminobenzoic acid 4-Aminobenzoic acid 2-Aminobiphenyl 4-Aminobiphenyl 4-Aminobutanoic acid 2-Aminoethanesulfonic acid ionized; std. state, m ⫽ 1 2-Aminoethanol 2-Aminohexanoic acid (norleucine) 4-Aminohexanoic acid 5-Aminohexanoic acid 6-Aminohexanoic acid (⫺)-2-Amino-3-hydroxybutanoic acid 2-Amino-2-(hydroxymethyl)1,1-propanediol 3-Aminonitroguanidine 5-Aminopentanoic acid 5-Aminotetrazole 3-Amino-1,2,4-triazole Aniline Anthracene 9,10-Anthraquinone D-(⫺)-Arabinose [also (⫹)-] (⫹)-Arginine L-(⫹)-Ascorbic acid L-(⫹)-Asparagine L-(⫹)-Aspartic acid

Physical State

⌬f H⬚ kJ · mol⫺1

c c c c c c c g c lq lq lq lq lq

96.0 ⫺561.2 ⫺604.0 ⫺563.6 ⫺558.0 ⫺777.8 ⫺827.0 190.5 ⫺1000.7 ⫺10.0 ⫺91.0 ⫺406.0 ⫺385.1 ⫺395.3

c c c c c c c c c c c c aq lq c

⫺284.1 ⫺173.3 ⫺182.1 166.4 159.2 ⫺400.9 ⫺411.6 ⫺412.9 112.2 81.2 ⫺581.0 ⫺785.9 ⫺719.8

c c c c

⫺646.2 ⫺643.3 ⫺639.1 ⫺759.5

c

717.8

c c c c lq g c c c c c c c

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

299.6 ⫺369.4 ⫺370.5 ⫺372.3

151.1 132.3 129.3 132.3

⫺489.9 ⫺533.0

213.5 195.2

⫺762.3

186.7

⫺79.3

218.0

⫺562.3 ⫺509.8

154.1 200.1

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 147.0

140.7 195.5

⫺639.1

22.1 ⫺604.1 ⫺207.8 76.8 31.3 87.5 129.2 ⫺207.5 ⫺1057.9 ⫺623.5 ⫺1164.6 ⫺789.4 ⫺973.3

149.2 ⫺7.0 286.0

191.4 317.9 207.6

191.9 107.9 210.5

⫺240.5

250.8

232.0

⫺530.6 ⫺730.7

174.6 170.2

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(McGHP)

RIGHT

INTERACTIVE

6.7

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance cis-Azobenzene trans-Azobenzene Azoisopropane Azomethane Azomethane-d6 Azopropane Azulene Barbituric acid Benzaldehyde Benzamide Benzanilide 1,2-Benzanthracene 2,3-Benzanthracene 1,2-Benzanthracene9,10-dione Benzene Benzeneboronic acid 1,2-Benzenediamine 1,3-Benzenediamine 1,4-Benzenediamine 1,3-Benzenedicarboxylic acid 1,4-Benzenedicarboxylic acid 1,2,4,5-Benzenetetracarboxylic acid Benzenethiol (thiophenol) 1,2,3-Benzenetricarboxylic acid 1,2,4-Benzenetricarboxylic acid 1,3,5-Benzenetricarboxylic acid 1,2,3-Benzenetriol 1,2,4-Benzenetriol 1,3,5-Benzenetriol p-Benzidine Benzil Benzoic acid Benzoic anhydride Benzonitrile Benzo[def]phenanthrene Benzophenone Benzo[f]quinoline Benzo[h]quinoline 1,4-Benzoquinone Benzo[b]thiophene 1,2,3-Benzotriazole Benzotrifluoride Benzoyl bromide Benzoyl chloride Benzoylformic acid N-Benzoylglycine

Physical State

⌬f H⬚ kJ · mol⫺1

c c g g g g g c lq c c c c c

310.2 365.2 35.8 148.8 119.3 51.5 289.1 ⫺637.2 ⫺87.0 ⫺202.6 ⫺93.4 170.9 160.4 ⫺231.9

lq g c c c c c c c lq g c c c c c c c c c c lq g c c c c c c c lq lq lq c c

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1

239.7 218.3

289.9 305.7

78.0 90.6

353.4

338.1

128.5

9.4

top of rh base of rh cap height base of text

172.0

359.2

215.5

49.0 82.6 ⫺720.1 ⫺0.3 ⫺7.8 3.1 803.0 816.1 1571.0

124.4 129.7

173.4 269.2

136.0 82.4

63.7 111.3 ⫺1160.0 ⫺1179.0 ⫺1190.0 ⫺551.1 ⫺563.8 ⫺584.6 70.7 ⫺153.9 ⫺385.2 ⫺415.4 163.2 215.8 125.5 ⫺34.5 150.6 149.7 ⫺185.7 100.6 250.0 ⫺636.7 ⫺107.3 ⫺158.0 ⫺482.4 ⫺609.8

134.0 147.6

222.8 336.9

173.2 104.9

⫺245.3

167.6

146.8

260.8 269.5 140.2

209.1 321.0 224.8 245.2

165.2 109.1 236.0 224.8

⫺83.6

162.8

129.0

⫺369.57

239.3

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(McGHP)

6.8

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Benzoyl iodide 3,4-Benzphenanthrene Benzylamine Benzyl alcohol Benzyl bromide Benzyl chloride N-Benzyldiphenylamine Benzyl ethyl sulfide Benzyl iodide Benzyl methyl ketone Benzyl methyl sulfide Bicyclo[1.1.0]butane Bicyclo[2.2.1]hepta2,5-dione Bicyclo[2.2.1]heptane Bicyclo[4.1.0]heptane Bicyclo[2.2.1]heptene Bicyclo[3.1.0]hexane Bicyclohexyl Bicyclo[2.2.2]octane Bicyclo[4.2.0]octane Bicyclo[5.1.0]octane Bicyclo[2.2.2]oct-2-ene Bicyclopropyl Biphenyl 2-Biphenylcarboxylic acid (1,1⬘-Biphenyl)-4,4⬘diamine Biphenylene Bis(2-chloroethyl) ether Bis(dimethylthiocarbonyl) disulfide Bis(2-hydroxyethyl) ether Bromoacetone Bromoacetylene Bromobenzene 4-Bromobenzoic acid 1-Bromobutane 2-Bromobutane Bromochlorodifluoromethane 1-Bromo-2-chloroethane Bromochlorofluoromethane Bromochloromethane 1-Bromo-2-chloro-1,1,2trifluoroethane 2-Bromo-2-chloro-1,1,1trifluoroethane 1-Bromodecane

Physical State

⌬f H⬚ kJ · mol⫺1

lq c lq lq lq lq c lq lq lq lq g lq

⫺53.5 184.9 34.2 ⫺160.7 16.0 ⫺32.6 184.7 ⫺4.9 57.3 ⫺151.9 26.2 217.1 213.0

c lq lq g lq c g g g g c c c

⫺95.1 ⫺36.7 90.0 38.6 ⫺273.7 ⫺146.9 ⫺26.2 ⫺16.6 ⫺23.3 129.3 99.4 ⫺349.0 70.7

c lq c

334.0

lq g g g lq c lq lq g g lq g lq g g

⫺1621.0 ⫺571.1 ⫺181.0

g

⫺690.4

lq

⫺344.7

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺27.5

216.7

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

218.0 182.4

203.9

254.2

130.0

209.4

198.4

220.9 41.6

126.0

441.0

135.1

253.7 219.2

55.7 154.3

60.9 ⫺378.3 ⫺143.8 ⫺154.8 ⫺120.3 ⫺471.5

⫺12.9 ⫺19.25 ⫺25.8 ⫺448.4

369.8

109.3

370.3 318.5

⫺295.0

⫺278.6

304.3

110.8 74.6 130.127 63.2 52.7

⫺50.2 ⫺644.8

⫺39.3

287.6

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(McGHP)

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INTERACTIVE

6.9

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Bromodichlorofluoromethane Bromodichloromethane Bromodifluoromethane Bromoethane Bromoethylene (vinyl bromide) Bromofluoromethane 1-Bromoheptane 1-Bromohexane Bromoiodomethane Bromomethane 2-Bromo-2-methylpropane 1-Bromooctane Bromopentafluoroethane 1-Bromopentane 1-Bromopropane 2-Bromopropane cis-1-Bromopropene 3-Bromopropene N-Bromosuccinimide ␣-Bromotoluene Bromotrichloromethane Bromotrifluoroethane Bromotrifluoromethane Bromotrimethylsilane Bromotrinitromethane Brucine 1,2-Butadiene 1,3-Butadiene 1,3-Butadiyne Butanal Butanamide Butane 1,2-Butanediamine (⫾)-1,2-Butanediol 1,3-Butanediol 1,4-Butanediol 2,3-Butanediol Butanedinitrile 2,3-Butanedione 1,4-Butanedithiol

Physical State g g g lq g lq g g lq lq g lq g lq g lq g lq g lq g lq g g g c lq g g g lq g c g lq g g lq g lq lq g lq lq lq lq lq c lq lq lq

⌬f H⬚ kJ · mol⫺1

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1

⫺269.5 ⫺58.6 ⫺424.9 ⫺90.5 ⫺61.9

⫺246.8 ⫺42.5 ⫺447.3 ⫺25.8 ⫺23.9

330.6 316.4 295.1 198.7 286.7

79.2 ⫺252.7 ⫺218.4 ⫺194.2 50.2

81.7 ⫺241.5

275.8 276.3

80.0 67.4 58.7 100.8 64.5 107.715 55.4 49.2

39.2

453.0 307.5

⫺35.4 ⫺163.8 ⫺132.4 ⫺245.1 ⫺1064.4 ⫺170.2 ⫺129.0 ⫺121.8 ⫺87.0 ⫺130.5 ⫺99.4 40.8 45.2 ⫺335.9 23.4 ⫺41.1 ⫺694.5 ⫺648.3 ⫺325.9 80.3 ⫺496.2 162.3 88.5 110.0 472.8 ⫺239.2 ⫺204.9 ⫺346.9

⫺26.3

246.4

⫺28.2

332.0

⫺5.7

408.8

⫺22.5

330.9

⫺27.2

316.2

132.2 89.4

⫺12.4

332.8

85.3

297.8(5)

69.3

⫺125.6 ⫺120.2 ⫺523.6 ⫺501.0 ⫺503.3 ⫺541.5 139.7

top of rh base of rh cap height base of text

203.5 78.77 42.5 151.0 116.5

132.2 86.4

⫺622.6

199.5 150.7 444.0

293.0 199.0 278.7 250.0

⫺114.8

243.7

80.1 123.6 79.5 73.6 163.7 103.4

⫺17.2

310.1

104.5⫺0.5 97.5

223.4

227.230 200.1 213.0 160.562

⫺365.8 ⫺105.7

short standard long

DEAN #37261

LEFT

(McGHP)

6.10

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Butanenitrile 1-Butanethiol 2-Butanethiol Butanoic acid Butanoic anhydride 1-Butanol (⫾)-2-Butanol 2-Butanone Butanophenone trans-2-Butenal cis-Butenedinitrile 1-Butene cis-2-Butene trans-2-Butene cis-2-Butenenitrile trans-2-Butenenitrile 3-Butenenitrile cis-2-Butenoic acid trans-2-Butenoic acid cis-2-Butenedioic acid trans-2-Butenedioic acid 1-Buten-3-yne 2-Butoxyethanol N-Butylacetamide Butyl acetate Butylamine sec-Butylamine tert-Butylamine Butylbenzene sec-Butylbenzene tert-Butylbenzene sec-Butyl butanoate Butyl chloroacetate Butyl 2-chlorobutanoate Butyl 3-chlorobutanoate Butyl 4-chlorobutanoate Butyl 2-chloropropanoate Butyl 3-chloropropanoate Butyl crotonate Butylcyclohexane

Physical State lq g lq lq lq lq lq g lq g lq g lq lq c lq g lq g g lq lq g lq c c c g lq lq lq lq g lq g g g lq g lq lq lq lq lq lq lq lq lq lq lq g

⌬f H⬚ kJ · mol⫺1 ⫺5.8 33.6 ⫺124.7 ⫺131.0 ⫺533.8 ⫺327.3 ⫺275.0 ⫺342.6 ⫺292.9 ⫺273.3 ⫺238.5 ⫺188.9 ⫺138.7 268.2 ⫺20.8 0.1 ⫺29.8 ⫺7.1 ⫺11.4 95.1 95.1 159.7 ⫺347.0 ⫺430.5 ⫺788.7 ⫺811.1 304.6 ⫺380.8 ⫺529.2 ⫺127.7 ⫺92.0 ⫺137.5 ⫺104.6 ⫺150.6 ⫺121.0 63.2 ⫺13.1 ⫺66.4 ⫺70.7 ⫺492.6 ⫺538.4 ⫺655.2 ⫺610.9 ⫺618.0 ⫺572.0 ⫺558.2 ⫺467.8 ⫺263.1 ⫺213.4

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

108.7 4.1 ⫺0.17 ⫺377.7

325.4 276.0 271.4 222.2

⫺162.5 ⫺150.8 ⫺177.0 ⫺167.6 ⫺151.4

225.8 362.8 214.9 359.5 239.1 339.9

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 15967 97.0 171.2 178.6 283.7 177.0 122.6 196.9 113.3 158.9 101.7 95.4

65.9 63.0

227.0 305.6 219.9 300.8 296.5

118.0 85.7 127.0 78.9 87.8

193.4

298.4

82.1

306.0

279.4

73.2 281.0

71.3

49.2

363.3

40.7

351.3

28.9

337.9

144.7

439.5

227.8 179.2 118.6 117.2 192.1 120.0 243.4 416.3 238.0

56.4

345.0 458.5

271.0 207.1

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.11

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Butylcyclopentane Butyl dichloroacetate Butyl ethyl ether Butyl ethyl sulfide (3-thiaheptane) tert-Butyl ethyl sulfide Butyl formate tert-Butyl hydroperoxide Butyllithium Butyl methyl ether tert-Butyl methyl ether Butyl methyl sulfide (2-thiahexane) tert-Butyl methyl sulfide Butyl methyl sulfone tert-Butyl methyl sulfone cis-Butyl 9-octadecanoate tert-Butyl peroxide Butyl trichloroacetate Butylurea Butyl vinyl ether 1-Butyne 2-Butyne 2-Butynedinitrile 2-Butynedioic acid 3-Butynoic acid ␥-Butyrolactone (⫹)-Camphor ⑀-Caprolactam 9H-Carbazole Carbonyl bromide Carbonyl chloride Carbonyl chloride fluoride Carbonyl fluoride Chloroacetamide Chloroacetic acid Chloroacetyl chloride Chloroacetylene 2-Chlorobenzaldehyde 3-Chlorobenzaldehyde 4-Chlorobenzaldehyde Chlorobenzene 2-Chlorobenzoic acid 3-Chlorobenzoic acid 4-Chlorobenzoic acid Chloro-1,4-benzoquinone 1-Chlorobutane (⫾)-2-Chlorobutane 2-Chlorobutanoic acid

Physical State

⌬f H⬚ kJ · mol⫺1

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

g lq lq g

⫺168.3 ⫺550.2

61.4

456.2

177.5

⫺125.2

32.0

453.0

159.0 162.0

lq lq lq lq lq lq lq

⫺187.3

lq lq c lq lq lq c lq g g g c c lq c c c g g g g c c lq g lq lq c lq c c c c lq g lq g lq

top of rh base of rh

200.2 ⫺293.6 ⫺132.2 ⫺290.6 ⫺313.6 ⫺142.8 ⫺156.9 ⫺535.8 ⫺556.0 ⫺816.9 ⫺380.9 ⫺545.8 ⫺419.5 ⫺218.8 165.2 145.7 529.2 ⫺577.4 ⫺241.8 ⫺420.9 ⫺319.4 ⫺329.4 101.7 ⫺96.2 ⫺219.1

17.1

202.1 185.4

295.3 265.3 307.5

192.7 187.5 200.9

276.1

199.9

290.8 283.3

232.0 81.4 78.0

141.4 271.2 ⫺110.9 ⫺204.9

309.1 283.5 276.7

61.8 57.7 52.4 46.8

242.0

54.3

209.2

150.2

⫺639.8 ⫺338.5 ⫺510.5 ⫺283.7 ⫺118.4 ⫺126.0 ⫺146.4 11.0 ⫺404.5 ⫺423.3 ⫺428.9 ⫺220.6 ⫺188.1 ⫺154.6 ⫺192.8 ⫺161.2 ⫺575.5

89.2

163.2 ⫺38.8

358.1

175.0 107.6

⫺53.5

359.6

108.5

short standard long

DEAN #37261

LEFT

(McGHP)

6.12

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 3-Chlorobutanoic acid 4-Chlorobutanoic acid Chlorocyclohexane 1-Chloro-1,1-difluoroethane 1-Chloro-2,2-difluoroethylene 2-Chloro-1,1-difluoroethylene Chlorodifluoromethane 2-Chloro-1,4-dihydroxybenzene Chlorodimethylsilane 1-Chloro-2,3-epoxypropane 1-Chloroethane 2-Chloroethanol 1-Chloro-2-ethylbenzene 1-Chloro-4-ethylbenzene Chloroethylene (vinyl chloride) 2-Chloroethyl ethyl ether 2-Chloroethyl vinyl ether Chloroethyne 1-Chloro-1-fluoroethane 2-Chlorohexane Chlorofluoromethane Chlorohydroquinone Chloroiodomethane Chloromethane 1-Chloro-3-methylbutane 2-Chloro-2-methylbutane 2-Chloro-3-methylbutane 1-Chloro-2-methylpropane 2-Chloro-2-methylpropane 1-Chloronaphthalene 2-Chloronaphthalene 1-Chlorooctane Chloropentafluoroacetone Chloropentafluoroethane 1-Chloropentane 3-Chlorophenol 4-Chlorophenol 1-Chloropropane 2-Chloropropane

Physical State lq lq lq lq g g g lq g c lq lq lq g lq lq lq lq g g g g g lq g c g lq g lq g g g lq g lq g lq c lq g lq g lq g c c lq g lq g

⌬f H⬚ kJ · mol⫺1

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺315.5 ⫺331.4

⫺289.1 ⫺305.0

307.2 303.0 302.4

⫺482.6 ⫺382.81 ⫺79.8 ⫺148.5 ⫺136.8 ⫺112.1 ⫺295.4 ⫺54.1 ⫺51.7

⫺450.0

281.0

⫺59.3 ⫺60.5

190.8 275.8

125.1 104.3 62.6

53.6

263.9

89.4 53.7

197.0

241.9

54.3

⫺265.5

264.3

47.0

15.4

296.1

⫺58.5

234.6

⫺49.7

355.0

⫺64.1

322.2

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

⫺556.3 ⫺566.3 ⫺207.2

37.3 ⫺301.3 ⫺170.1 213.0 ⫺313.4 ⫺246.1 ⫺290.8 ⫺382.8 12.6 ⫺81.9 ⫺216.0 ⫺179.7 ⫺202.2 ⫺185.1 ⫺191.1 ⫺159.4 ⫺211.2 ⫺182.2 54.6 55.2 ⫺291.3 ⫺1121.0

130.521 82.5 72.1 93.0⫺41 55.9

75.6⫺24 40.8 175.1

158.6 108.5 172.8 114.2 212.6 198.5 184.2

⫺1188.8 ⫺213.2 ⫺175.0 ⫺206.4 ⫺197.9 ⫺160.6 ⫺131.9 ⫺172.1 ⫺144.9

⫺37.4

397.0

130.5

⫺50.7

319.1

132.2 84.6

⫺62.5

304.2

87.3

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.13

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 2-Chloro-1,3-propanediol 3-Chloro-1,2-propanediol 2-Chloropropanoic acid 3-Chloropropanoic acid 2-Chloro-1-propene 3-Chloro-1-propene (allyl chloride) N-Chlorosuccinimide ␣-Chlorotoluene o-Chlorotoluene 2-Chloro-1,1,1-trifluoroethane Chlorotrifluoroethylene Chlorotrifluoromethane Chlorotrimethylsilane Chlorotrinitromethane Chrysene (⫺)-Cinchonidine Cinchonine cis-Cinnamic acid trans-Cinnamic acid Cinnamic anhydride Citric acid Codeine monohydrate Creatine o-Cresol

m-Cresol p-Cresol

Cuban Cyanamide Cyanide (CN) Cyanogen Cyanogen bromide Cyanogen chloride Cyanogen fluoride Cyanogen iodide Cyclobutane Cyclobutanecarbonitrile Cyclobutene Cyclobutylamine Cyclododecane 1,3-Cycloheptadiene Cycloheptane

Physical State

⌬f H⬚ kJ · mol⫺1

lq lq lq c g lq

⫺517.5 ⫺525.3 ⫺522.5 ⫺549.3 ⫺21.0

g c lq lq g

⫺0.63 ⫺358.1 ⫺32.6

g g lq lq g c c c c c c c c c c lq g lq g c lq g c c g g g g g c g g lq g g c g lq

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

131.6

125.1

⫺505.5 ⫺707.8 ⫺384.1 ⫺27.1 18.4 145.3 29.7 31.0 ⫺315.0 ⫺338.5 ⫺347.7 ⫺1543.9 ⫺632.6 ⫺537.2 ⫺204.6 ⫺128.6 ⫺194.0 ⫺132.3 ⫺199.3 ⫺125.4 541.3 58.8 437.6 306.7 140.5 138.0 ⫺639.8 166.2 205.5 27.7 103.0 156.7 41.2 ⫺306.6 94.3 ⫺156.6

43.6

306.7

75.4

326.4

166.8 154.6

⫺523.8 ⫺667.4

322.1 285.4

83.9 66.9

⫺1236.4

166.2

165.4 37.1 ⫺40.5 ⫺30.9

407.5 297.2 165.3 131.0

357.6 212.6 356.8 167.3 347.6

154.6 233.640 130.3 224.9 122.5 150.2 221.040 124.5

29.2 56.9 46.9 45.0 41.8

185.0 196.6 110.0

202.6 241.9 248.3 236.2 224.7 96.2 256.8 265.4

174.7

263.5

67.1

54.1

242.6

123.1

48.3 72.2

short standard long

DEAN #37261

LEFT

(McGHP)

6.14

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Cycloheptanone 1,3,5-Cycloheptatriene Cycloheptene Cyclohexane cis-Cyclohexane-1,2dicarboxylic acid trans-Cyclohexane-1,2dicarboxylic acid Cyclohexanethiol Cyclohexanol Cyclohexanone Cyclohexene 1-Cyclohexenylmethanol Cyclohexylamine Cyclohexylbenzene Cyclohexylcyclohexane Cyclooctane Cyclooctanone 1,3,5,7-Cyclooctatetraene Cyclooctene 1,3-Cyclopentadiene Cyclopentane cis-1,2-Cyclopentanediol trans-1,2-Cyclopentanediol Cyclopentanethiol Cyclopentanol Cyclopentanone Cyclopentene 1-Cyclopentenylmethanol Cyclopentylamine Cyclopropane Cyclopropanecarbonitrile Cyclopropene Cyclopropylamine Cyclopropylbenzene (⫺)-Cysteine (⫺)-Cystine Cytosine Decafluorobutane cis-Decahydronaphthalene trans-Decahydronaphthalene Decanal Decane Decanedioic acid 1,10-Decanediol

Physical State

⌬f H⬚ kJ · mol⫺1

lq lq g lq g c

⫺299.4 142.2 ⫺9.2 ⫺156.4 ⫺123.4 ⫺961.1

c

⫺970.7

lq g lq lq g lq lq lq lq lq lq lq lq lq g lq g c c lq lq lq lq g lq lq g g g lq g lq c c c lq lq lq g lq c c

⫺140.7 ⫺96.1 ⫺348.1 ⫺271.2 ⫺226.1 ⫺38.5 ⫺382.4 ⫺147.7 ⫺76.6 ⫺329.3 ⫺167.7 ⫺326.0 254.5 ⫺74.0 134.3 ⫺105.1 ⫺76.4 ⫺484.9 ⫺489.9 ⫺89.5 ⫺300.1 ⫺235.7 4.4 34.0 34.3 ⫺95.1 53.3 182.8 277.1 45.8 77.0 100.3 ⫺534.1 ⫺1032.7 ⫺221.3 ⫺219.4 ⫺230.6 ⫺330.9 ⫺300.9 ⫺1082.8 ⫺693.5

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1

243.1

214.6

162.8

26.7 31.8

204.4 298.3

154.9 106.3

255.6

192.6

199.6 255.6 322.2 214.6

208.2 182.2 109.7 148.3

⫺133.3 ⫺90.8 101.6

cap height base of text

261.3

358.6

220.3

184.0

179.3 36.4 38.6

267.8 204.3 292.9

128.9 83.0

46.8 ⫺127.8

256.9 206.3

108.5 110.8

201.3 291.8

165.2 184.1 154.5 122.4 75.1

104.4

241.0 237.4

181.2 55.6

223.3 187.7

147.1

286.3

132.6 68.9 57.7 ⫺66.5 17.5

265.0 265.0 578.6 425.5

127.220 232.0 228.5 239.7 314.4

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.15

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 1-Decanenitrile 1-Decanethiol Decanoic acid 1-Decanol 1-Decene 1-Decyne Deoxybenzoin Diacetamide Diacetyl peroxide 1,2-Diallyl phthalate 2,2⬘-Diaminodiethylamine 2,6-Diaminopyridine Diazomethane Dibenz[de,kl]anthracene 1,2-Dibenzoylethane trans-1,2-Dibenzoylethylene Dibenzoylmethane Dibenzoyl peroxide Dibenzyl Dibenzyl sulfide Dibenzyl sulfone 1,2-Dibromobutane 1,3-Dibromobutane 1,4-Dibromobutane 2,3-Dibromobutane Dibromochlorofluoromethane Dibromochloromethane 1,2-Dibromo-1-chloro-1,2,2trifluoroethane 1,2-Dibromocycloheptane 1,2-Dibromocyclohexane 1,2-Dibromocyclooctane Dibromodifluoroethane Dibromodichloromethane Dibromodifluoromethane 1,1-Dibromoethane 1,2-Dibromoethane cis-1,2-Dibromoethylene trans-1,2-Dibromoethylene Dibromofluoromethane Dibromomethane 1,3-Dibromo-2-methylpropane 1,3-Dibromotetrafluoroethane 1,2-Dibromopropane 1,2-Dibromotetrafluoroethane

Physical State lq lq g c lq lq g c c lq lq lq c g c c c c c c c c g lq g g g g lq g lq lq lq g g g lq lq g g g g lq g g lq g lq g lq

⌬f H⬚ kJ · mol⫺1 ⫺158.4 ⫺276.5 ⫺211.5 ⫺713.7 ⫺478.1 ⫺173.8 41.2 ⫺71.0 ⫺489.0 ⫺535.3 ⫺550.6

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

61.4

476.1 610.1

350.4 255.6

⫺132.2 105.0 252.2

430.5 425.0 524.5

370.6 300.8 219.7

25440 ⫺6.5 192.5 182.8 ⫺255.6 ⫺114.7 ⫺223.5 ⫺369.6 44.1 99.0 ⫺282.6 ⫺91.5 ⫺148.0 ⫺87.8 ⫺102.0 ⫺231.8 ⫺20.9 ⫺691.7

217.8

242.8

109.8

319.2

260.0

269.4

255.2

⫺13.1

408.8

127.1

⫺223.4 ⫺18.8

342.8 327.7

82.4 69.2

⫺19.5 ⫺419.1

327.7 347.8 325.3

80.8 87.1 77.0

⫺20.9

223.3

136.0

⫺223.4

⫺221.1

313.3 313.5 316.8

⫺14.8 ⫺137.6 ⫺817.7 ⫺789.1

⫺16.2

293.2

68.8 70.3 65.1 105.3 54.7

⫺71.5

⫺17.7

376.1

⫺656.6 ⫺157.6 ⫺162.8 ⫺173.3 ⫺36.9 ⫺29.3 ⫺429.7 ⫺66.2 ⫺79.2 ⫺37.5

52.5

160.0 102.8 180.3

short standard long

DEAN #37261

LEFT

(McGHP)

6.16

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Dibutoxymethane Dibutylamine Dibutyl disulfide Di-tert-butyl disulfide Dibutyl ether Di-sec-butyl ether Di-tert-butyl ether Dibutylmercury Dibutyl peroxide Dibutyl 1,2-phthalate Dibutyl sulfate Dibutyl sulfide Di-tert-butyl sulfide Dibutyl sulfite Dibutyl sulfone Dichloroacetic acid ionized Dichloroacetyl chloride 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene

Dichlorodifluoromethane 1,3-Dichlorobutane 1,4-Dichlorobutane Dichlorodimethylsilane Dichlorodiphenylsilane 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene Dichlorofluoromethane 1,1-Dichloro-1-fluoroethane 1,1-Dichlorofluoroethylene 1,1-Dichlorofluoromethane Dichloromethane Dichloropentadienyliron 1,2-Dichloropropane

Physical State lq lq g lq lq g lq g lq g lq lq c lq lq lq lq c lq aq lq lq g lq g c lq g lq g g g g lq lq g lq g lq g g lq g g g g lq lq g c lq

⌬f H⬚ kJ · mol⫺1 ⫺549.4 ⫺206.0 ⫺160.6 ⫺255.2 ⫺377.9 ⫺332.8 ⫺401.5 ⫺360.9 ⫺399.6 ⫺362.0 ⫺97.9 ⫺380.7 ⫺842.6 ⫺904.6 ⫺220.7 ⫺232.4 ⫺693.1 ⫺610.2 ⫺496.3 ⫺507.1 ⫺280.4 ⫺17.5 30.2 ⫺20.7 25.7 ⫺42.3

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1

53.9

572.8

292.9 231.1

⫺88.5

500.4

278.2 204.0

276.1

498.0 32.2

405.1

82.7

341.5

78.6

343.5

22.5

77.2

175.4 336.7

⫺477.4 ⫺195.0 ⫺183.4 ⫺461.1 ⫺278.2 ⫺158.4 ⫺127.7 ⫺167.4 ⫺126.4 ⫺23.9 2.8 4.6 ⫺23.1 5.0 ⫺283.0

⫺439.4

300.8

147.8 113.9 117.2 72.3

335.4

101.1

⫺124.2 ⫺95.4 141.0 ⫺198.8

cap height base of text

⫺73.8

305.1

⫺73.9

308.4

25.4 24.4

289.1 289.5

28.6 ⫺253.0

289.9 293.1 320.2 313.9

⫺68.9

177.8 270.3

284.3

162.4 113.5 171 113.8

126.3 76.2 128.4 78.7 111.3 67.0 65.1 116.8 66.7 6l.0 88.7 76.5 112.6 101.2 51.0

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.17

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 1,3-Dichloropropane 2,2-Dichloropropane 1,3-Dichloro-2-propanol 2,3-Dichloro-1-propanol 2,3-Dichloropropene 1,2-Dichlorotetrafluoromethane 2,2-Dichlorotetrafluoroethane 2,2-Dichloro-1,1,1-trifluoroethane Dicyanoacetylene Dicyanobenzene 1,4-Dicyanobutane 1,4-Dicyano-2-butyne Dicyanodiamide Dicyclopentadiene Diethanolamine 1,1-Diethoxyethane 1,2-Diethoxyethane Diethoxymethane 1,3-Diethoxypropane 2,2-Diethoxypropane Diethylamine Diethylamine hydrochloride Diethylbarbituric acid (veronal) 1,2-Diethylbenzene 1,3-Diethylbenzene 1,4-Diethylbenzene Diethyl carbonate cis-1,2-Diethylcyclopropane trans-1,2-Diethylcyclopropane Diethyl disulfide Diethylenediamine Diethylene glycol Diethylene glycol dibutyl ether Diethylene glycol diethyl ether Diethylene glycol dimethyl ether Diethylene glycol monoethyl ether Diethylene glycol monomethyl ether Diethyl ether

Physical State

⌬f H⬚ kJ · mol⫺1

g g g lq lq lq lq g lq g

⫺162.8 ⫺159.2 ⫺173.2 ⫺385.4 ⫺381.3 ⫺73.3

lq c lq c c c c lq lq lq lq lq lq lq g c c

500.4 275.4 85.1 366.5 22.6 116.7 ⫺493.8

g g g lq lq lq lq g c lq g lq lq

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺83.1 ⫺82.6 ⫺84.6

354.8 367.2 326.0

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 98.2 99.6 105.9

164.2 ⫺916.3 ⫺960.2 352.8

⫺491.4 ⫺451.4 ⫺450.4 ⫺482.1 ⫺538.5 ⫺103.7 ⫺72.2 ⫺358.6 ⫺747.7 ⫺19.0 ⫺21.8 ⫺22.3 ⫺681.5 ⫺79.9 83.3 ⫺120.0 ⫺79.4 ⫺13.4 ⫺628.5 ⫺571.1

111.7 102.5

128.7 179.5

129.3

118.8

233.530 238.0 259.4

169.2 115.7

72.1

352.2

141.1 136.7 137.9

434.3 439.3 434.0

182.6 176.9 176.2 212.4

9.5 22.3 240.2

269.3 414.5 85.8

171.4 141.3

441.0

244.8 135.1 45220 341.415

lq

274.1

lq

301.0

lq

271.1

lq g

top of rh base of rh

⫺279.5 ⫺252.1

⫺116.7 ⫺122.3

172.4 342.7

172.6 119.5

short standard long

DEAN #37261

LEFT

(McGHP)

6.18

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Di-2-ethylhexyl phthalate Diethyl malonate Diethylmercury Diethyl oxalate 3,3-Diethylpentane Diethyl peroxide Diethyl 1,2-phthalate Diethyl selenide Diethyl sulfate Diethyl sulfide Diethyl sulfite Diethyl sulfone Diethyl sulfoxide N,N-Diethylurea Diethylzinc 1,2-Difluorobenzene 1,3-Difluorobenzene 1,4-Difluorobenzene 2,2⬘-Difluorobiphenyl 4,4⬘-Difluorobiphenyl 1,1-Difluoroethane 1,1-Difluoroethylene Difluoromethane 9,10-Dihydroanthracene 1,2-Dihydronaphthalene 1,4-Dihydronaphthalene Dihydro-2H-pyran 5,12-Dihydrotetracene 2,3-Dihydrothiophene 2,5-Dihydrothiophene 2,5-Dihydrothiophene-1,1dioxide 2⬘,4-Dihydroxyacetophenone 1,2-Dihydroxybenzene (pyrocatechol) 1,3-Dihydroxybenzene 1,4-Dihydroxybenzene (p-hydroquinone) Dihydroxymalonic acid 2,4-Dihydroxy-5-methylpyrimidine 2,4-Dihydroxy-6-methylpyrimidine Diiodoacetylene 1,2-Diiodobenzene

Physical State lq lq lq lq lq lq lq lq lq lq g lq c lq c lq lq g lq g lq g c c lq g g g c lq lq lq c lq g g c

⌬f H⬚ kJ · mol⫺1 ⫺805.5 30.1 ⫺805.5 ⫺275.4 ⫺223.3 ⫺776.6 ⫺96.2 ⫺813.2 ⫺119.4 ⫺83.6 ⫺600.7 ⫺515.5 ⫺268.0 ⫺372.2 16.7 ⫺330.0 ⫺293.8 ⫺343.9 ⫺309.2 ⫺342.3 ⫺306.7 ⫺295.9 ⫺296.5 ⫺497.0 ⫺335.0 ⫺452.2 66.4 71.5 84.2 ⫺157.4 106.4 52.9 90.7 86.9 318.9

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 704.7 260.7 182.8 278.2

425.1

366.1

269.3 368.0

171.4 117.0

⫺257.0

222.6 321.9 223.8 320.4

⫺252.8

315.6

159.0 106.5 159.1 106.3 157.5 106.9

⫺443.0 ⫺321.5 ⫺425.4

282.4 266.2 246.6

118.4 67.8 60.1 42.9

133.5 131.6

303.5 297.1

79.8 83.3

17.8

⫺242.0

c c

⫺573.6 ⫺354.1

⫺210.0

150.2

132.2

c c

⫺368.0 ⫺364.5

⫺209.2 ⫺207.0

147.7 140.2

131.0 136.0

c c

⫺1216.3 ⫺468.2

c

⫺456.9

g c

313.1

70.3

172.4

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.19

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 1,3-Diiodobenzene 1,4-Diiodobenzene 1,2-Diiodoethane Diiodomethane 1,2-Diiodopropane 1,3-Diiodopropane Diisobutylamine Diisopentyl ether Diisopropylamine Diisopropyl ether Diisopropylmercury Diisopropyl sulfide Diketene 1,2-Dimethoxybenzene 1,1-Dimethoxybutane 2,2-Dimethoxybutane 1,1-Dimethoxyethane 1,2-Dimethoxyethane Dimethoxymethane 1,1-Dimethoxypentane 2,2-Dimethoxypentane 1,1-Dimethoxypropane 2,2-Dimethoxypropane 1,1-Dimethoxy-2-methylpropane N,N-Dimethylacetamide Dimethylamine 4-(Dimethylamino)benzaldehyde Dimethylaminomethanol N,N-Dimethylaminotrimethylsilane N,N-Dimethylaniline 2,6-Dimethylaniline 2,3-Dimethylbenzoic acid 2,4-Dimethylbenzoic acid 2,5-Dimethylbenzoic acid 2,6-Dimethylbenzoic acid 3,4-Dimethylbenzoic acid 3,5-Dimethylbenzoic acid 3,3⬘-Dimethylbiphenyl 2,2-Dimethylbutane 2,3-Dimethylbutane 3,3-Dimethyl-2-butanone

Physical State

⌬f H⬚ kJ · mol⫺1

c lq c g lq g g lq lq lq lq lq g lq lq g lq lq lq lq lq lq lq lq lq lq lq lq

187.0 ⫺30.0 160.7 75.0 66.9 119.5 35.6 ⫺9.0 ⫺218.5 ⫺178.5 ⫺351.5 ⫺319.2 ⫺13.0 ⫺181.6 ⫺142.1 ⫺233.1 ⫺290.4 ⫺468.1 ⫺485.1 ⫺420.2 ⫺376.7 ⫺377.8 ⫺494.6 ⫺509.2 ⫺443.3 ⫺459.0 ⫺476.2

lq lq g c

⫺278.3 ⫺43.9 ⫺18.5 ⫺137.6

lq lq

⫺253.6 ⫺279.5

lq lq c c c c c c lq lq g lq g lq

47.7

⌬f G⬚ kJ · mol⫺1

78.5 90.4 95.8

S⬚ J · deg⫺1 · mol⫺1

348.5 174.1 309.7

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

82.3 134.0 57.7

379100

⫺450.4 ⫺458.5 ⫺456.1 ⫺440.7 ⫺468.8 ⫺466.4 20.0 ⫺213.8 ⫺186.1 ⫺207.4 ⫺178.3 ⫺328.6

⫺121.9

390.2

216.8 158.3

27.1

313.0 415.5

232.0 169.2

244.0

193.3 161.3

182.3 273.0

175.6 137.7 70.7

70.0 68.5

214.629 238.9

⫺9.2 ⫺4.1

272.5 358.2 287.8 365.8

191.9 141.9 189.7 140.5

short standard long

DEAN #37261

LEFT

(McGHP)

6.20

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 2,3-Dimethyl-1-butene 2,3-Dimethyl-2-butene 3,3-Dimethyl-1-butene 2,3-Dimethyl-2-butenoic acid Dimethylcadmium 1,1-Dimethylcyclohexane cis-1,2-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane cis-1,3-Dimethylcyclohexane trans-1,3-Dimethylcyclohexane cis-1,4-Dimethylcyclohexane trans-1,4-Dimethylcyclohexane 1,1-Dimethylcyclopentane cis-1,2-Dimethylcyclopentane trans-1,2-Dimethylcyclopentane cis-1,3-Dimethylcyclopentane trans-1,3-Dimethylcyclopentane 1,1-Dimethylcyclopropane cis-1,2-Dimethylcyclopropane trans-1,2-Dimethylcyclopropane cis-2,4-Dimethyl-1,3-dioxane 4,5-Dimethyl-1,3-dioxane 5,5-Dimethyl-1,3-dioxane 4,4⬘-Dimethyldiphenylamine Dimethyl disulfide Dimethyl ether N,N-Dimethylformamide Dimethyl fumarate Dimethylglyoxime 2,2-Dimethylheptane 2,6-Dimethyl-4-heptanone 2,2-Dimethylhexane 2,3-Dimethylhexane 2,4-Dimethylhexane 2,5-Dimethylhexane 3,3-Dimethylhexane 3,4-Dimethylhexane Dimethyl hexanedioate cis-2,2-Dimethyl-3-hexene trans-2,2-Dimethyl-3-hexene cis-2,5-Dimethyl-3-hexene trans-2,5-Dimethyl-3-hexene

Physical State

⌬f H⬚ kJ · mol⫺1

⌬f G⬚ kJ · mol⫺1

⫺62.6 ⫺101.4 ⫺68.2 ⫺60.5 ⫺455.6 63.6 ⫺218.7 ⫺180.9 ⫺211.8 ⫺172.1 ⫺218.2 ⫺180.0 ⫺222.9 ⫺184.6 ⫺215.7 ⫺176.5 ⫺215.6 ⫺176.6 ⫺222.4 ⫺184.5 ⫺138.2 ⫺165.3 ⫺129.5 ⫺136.6 ⫺135.9 ⫺133.6 ⫺33.3 ⫺26.3 ⫺30.7 ⫺465.2 ⫺451.6 ⫺461.3 ⫺11.72 ⫺62.6 ⫺184.1 ⫺239.3 ⫺729.3 ⫺199.7 ⫺288.2 ⫺408.5 ⫺261.9 ⫺252.6 ⫺257.0 ⫺260.4 ⫺257.5 ⫺251.8 ⫺886.6 ⫺126.4 ⫺144.9 ⫺151.0 ⫺159.2

79.0

lq g g c lq lq g lq g lq g lq g lq g lq g lq g g lq g g g g lq lq lq lq lq lq c lq g lq lq c lq lq lq lq lq lq lq lq lq lq lq lq lq

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1

365.6 270.2 364.6 343.8

143.5 174.7 123.6 126.5 132.0 209.2 154.4 210.2 165.5 209.4 159.0 209.4 157.3 212.8 157.3 212.1 157.3 210.2 157.7 133.3

45.7 38.4 39.2 41.5

201.9 267.2 365.0 274.1 374.5 273.2 370.9 272.6 370.5 276.3 376.2 271.1 370.5 268.0 364.8 359.3 269.2 366.1 366.8 366.8 366.8

7.0 ⫺112.6

235.4 266.4

146.1 64.4 150.6

3.0 9.1 3.7 2.5 5.2 8.5

331.9 342.7 345.7 338.7 339.4 347.2

76.1 98.2 139.3 26.5 35.2 41.2 34.5 29.8 36.3 38.0 31.7 39.0

cap height base of text

134.14 134.5 134.5 134.5

297.3

249.2 246.6

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.21

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 5,5-Dimethylhydantoin 1,1-Dimethylhydrazine 1,2-Dimethylhydrazine 3,5-Dimethylisoxazole Dimethyl maleate Dimethylmaleic anhydride Dimethyl malonate Dimethylmercury 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane Dimethyl oxalate 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane Dimethyl pentanedioate 2,4-Dimethyl-3-pentanone 2,4-Dimethyl-1-pentene 4,4-Dimethyl-1-pentene 2,4-Dimethyl-2-pentene cis-4,4-Dimethyl-2-pentene trans-4,4-Dimethyl-2-pentene 2,7-Dimethylphenanthrene 4,5-Dimethylphenanthrene 9,10-Dimethylphenanthrene 2,3-Dimethylphenol 2,4-Dimethylphenol 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol 3,5-Dimethylphenol Dimethyl 1,2-phthalate Dimethyl 1,3-phthalate Dimethyl 1,4-phthalate 2,2-Dimethylpropane 2,2-Dimethylpropanenitrile 2,2-Dimethyl-1,3-propanediol 2,2-Dimethylpropanoic acid 2,2-Dimethylpropanoic anhydride 2,2-Dimethyl-1-propanol 2,3-Dimethylpyridine 2,4-Dimethylpyridine 2,5-Dimethylpyridine

Physical State

⌬f H⬚ kJ · mol⫺1

c lq lq lq lq c lq lq g lq

⫺533.3 48.9 52.7 ⫺63.2 ⫺703.8 ⫺581.6 ⫺795.8 59.8 94.4 ⫺7.7

lq lq g lq g lq g lq g lq lq g g g g g g c c c c lq c c c c lq c c lq g lq c lq lq

⫺756.3 ⫺238.3 ⫺205.9 ⫺233.1 ⫺198.9 ⫺234.6 ⫺201.7 ⫺234.2 ⫺201.2 ⫺205.9 ⫺352.9 ⫺311.5 ⫺83.8 ⫺81.6 ⫺88.7 ⫺72.6 ⫺88.8 36.4 89.0 47.7 ⫺241.2 ⫺228.7 ⫺246.6 ⫺237.4 ⫺242.3 ⫺244.4 ⫺678 ⫺730.0 ⫺732.6 ⫺168.0 ⫺39.8 ⫺551.2 ⫺564.4 ⫺779.9

lq lq lq lq

⫺399.4 19.4 16.2 18.7

⌬f G⬚ kJ · mol⫺1 206.7 212.6

S⬚ J · deg⫺1 · mol⫺1 198.0 199.2

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 164.1 171.0 263.2

140.3 146.1

209.0 306.0

0.1

300.3 392.9

83.3

3.1

414.0 303.2 396.6

221.1 166.0 218.3 166.0 224.2 166.0

2.6

399.7

166.0

318.0

233.7

0.7

206.9

303.1

⫺1.5

306.4 232.0

261.1 163.96 121.6 179.4

243.7 248.5 248.8

189.5 184.8 184.7

short standard long

DEAN #37261

LEFT

(McGHP)

6.22

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 2,6-Dimethylpyridine 3,4-Dimethylpyridine 3,5-Dimethylpyridine Dimethyl succinate 2,2-Dimethylsuccinic acid meso-2,3-Dimethylsuccinic acid Dimethyl sulfate Dimethyl sulfide Dimethyl sulfite Dimethyl sulfone

Dimethyl sulfoxide 1,5-Dimethyltetrazole 2,2-Dimethylthiacyclopropane 5,5-Dimethyl-4-thia-1-hexene N,N-Dimethylurea N,N’-Dimethylurea Dimethylzinc 2,3-Dinitroaniline 2,4-Dinitroaniline 2,5-Dinitroaniline 2,6-Dinitroaniline 3,4-Dinitroaniline 3,5-Dinitroaniline 2,4-Dinitroanisole 2,6-Dinitroanisole 1,2-Dinitrobenzene 1,3-Dinitrobenzene 1,4-Dinitrobenzene 1,1-Dinitroethane 1,2-Dinitroethane Dinitromethane 1,5-Dinitronaphthalene 2,4-Dinitro-1-naphthol 2,4-Dinitrophenol 2,6-Dinitrophenol 1,1-Dinitropropane 1,3-Dinitropropane 2,2-Dinitropropane 2,4-Dinitroresorcinol 2,4-Dinitrotoluene 2,6-Dinitrotoluene 1,3-Dioxane 1,4-Dioxane 1,3-Dioxolane

Physical State

⌬f H⬚ kJ · mol⫺1

lq lq lq lq c c

12.7 18.3 22.5 ⫺835.1 ⫺987.8 ⫺977.5

lq lq g lq c lq g lq c lq lq c c lq c c c c c c c c c c c lq lq lq g c c c c lq lq lq c c c lq lq g lq g

⫺735.5 ⫺65.4 ⫺37.5 ⫺523.6 ⫺450.1 ⫺373.1 ⫺204.2 188.7 ⫺24.2 ⫺90.7 ⫺319.1 ⫺312.1 23.4 ⫺11.7 ⫺67.8 ⫺44.4 ⫺50.6 ⫺32.6 ⫺38.9 ⫺186.6 ⫺189.1 ⫺1.8 ⫺27.4 ⫺38.7 ⫺148.2 ⫺165.2 ⫺104.9 ⫺58.9 30.5 ⫺181.4 ⫺232.6 ⫺210.0 ⫺163.2 ⫺207.1 ⫺181.2 ⫺415.5 ⫺71.6 ⫺51.0 ⫺379.7 ⫺353.9 ⫺315.8 ⫺333.5 ⫺298.0

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1

249.2 240.7 241.7

185.2 191.8 184.5

7.0

285.9

118.1 74.1

⫺302.5 ⫺272

142.0

⫺99.2

310.6 188.3

100.0 153.0

201.6

129.2

211.5 184.6

216.3 220.9

⫺188.1 ⫺180.8

270.2 299.8

cap height base of text

143.9 153.6 94.1 118.0

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.23

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 1,3-Dioxolan-2-one 1,3-Dioxol-2-one Dipentene Dipentyl ether N,N-Diphenylacetamide Diphenylacetylene Diphenylamine Diphenylboron bromide cis,cis-1,4-Diphenylbutadiene trans,trans-1,4-Diphenylbutadiene Diphenylbutadiyne 1,4-Diphenylbutane 1,4-Diphenyl-1,4-butanedione 1,4-Diphenyl-2-butene-1,4-dione Diphenyl carbonate Diphenyl disulfide Diphenyl disulfone Diphenyleneimine 1,1-Diphenylethane 1,2-Diphenylethane Diphenylethanedione Diphenyl ether 1,1-Diphenylethylene Diphenylethyne 6,6-Diphenylfulvene 1,2-Diphenylhydrazine Diphenylmercury Diphenylmethane 1,3-Diphenyl-2-propanone Diphenyl sulfide Diphenyl sulfone Diphenyl sulfoxide 1,3-Diphenylurea Dipropylamine Dipropyl disulfide Dipropyl ether Dipropylmercury Dipropyl sulfate Dipropyl sulfide Dipropyl sulfite Dipropyl sulfone Dipropyl sulfoxide 2,2’-Dipyridyl ketone 1,3-Dithiane 1,2-Dithiolane 1,3-Dithiolane

Physical State

⌬f H⬚ kJ · mol⫺1

c lq lq lq c c c lq c c

⫺581.6 ⫺459.9 ⫺50.8

c c c c c c c c lq lq c c lq lq c c c c c lq c lq c c c lq lq lq g lq lq lq g lq lq lq c g g g

518.4 ⫺9.9 ⫺256.2 ⫺114.7 ⫺401.2 ⫺148.5 ⫺643.2 126.8 48.7 51.5 ⫺154.0 ⫺32.1 ⫺14.9 172.4 312.4 197.4 221.3 279.5 71.7 89.7 ⫺84.0 163.4 ⫺225.0 9.7 ⫺122.6 ⫺156.1 ⫺171.3 ⫺328.8 ⫺292.9 ⫺20.9 ⫺859.0 ⫺171.5 ⫺125.3 ⫺646.8 ⫺548.2 ⫺329.4 ⫺19.7 ⫺10.0 0.0 10.0

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 133.950 249.4 250

⫺43.1 312.4 130.6 ⫺16.1 198.8 178.8

225.9

7.8 111.5 ⫺175.9

324.7 319.2 278.4

245.1 67.2

335.9 270.3

144.2

233.9 291.3

216.6 268.6

239.3 276.9

233.1

253.075 19.1 ⫺105.6

373.6 323.9 422.5

221.6 158.3

33.2

448.4

161.2

72.4 47.7 54.7

333.5 313.5 323.3

110.4 86.5 84.7

short standard long

DEAN #37261

LEFT

(McGHP)

6.24

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Divinyl ether Divinyl sulfone Docosanoic acid cis-13-Docosenic acid trans-13-Docosenic acid Dodecane Dodecanedioic acid Dodecanoic acid 1-Dodecanol 1-Dodecene 1-Dodecyne Dulcitol 1,2-Epoxybutane Ergosterol Ethane Ethane-d6 1,2-Ethanediamine 1,2-Ethanediol Ethanedithioamide Ethanedioyl dichloride 1,2-Ethanedithiol Ethanethiol Ethanol Ethene (see Ethylene) Ethoxybenzene 2-Ethoxyethyl acetate 2-Ethoxyethanol Ethyl acetate Ethylamine Ethyl 4-aminobenzoate N-Ethylaniline Ethylbenzene Ethyl benzoate 2-Ethylbenzoic acid 3-Ethylbenzoic acid 4-Ethylbenzoic acid 2-Ethyl-1-butene Ethyl trans-2-butenoate (ethyl crotonate) Ethyl carbamate Ethyl 4-chlorobutanoate

Physical State

⌬f H⬚ kJ · mol⫺1

lq g lq c c c lq g c c lq lq lq g g c lq c g g lq lq g c lq lq lq g lq g

⫺39.8 ⫺13.6 ⫺207.4 ⫺983.0 ⫺866.0 ⫺960.7 ⫺350.9 ⫺289.7 ⫺1130.0 ⫺774.6 ⫺737.9 ⫺528.5 ⫺226.2 ⫺165.4 ⫺0.04 ⫺1346.8 ⫺168.9 ⫺789.9 ⫺84.0 ⫺107.4 ⫺63.0 ⫺455.3 ⫺392.2 ⫺20.8 ⫺367.6 ⫺54.4 ⫺73.6 ⫺46.1 ⫺277.6 ⫺234.8

lq lq lq lq g lq g c lq lq g lq c c c g lq

⫺152.6

c lq

⫺520.5 ⫺566.5

⌬f G⬚ kJ · mol⫺1

28.1 50.0

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1

490.6 622.5

376.0 280.3

484.8 618.3 602.4

404.3 438.1 360.7 269.6 265.4

230.9

147.0

⫺323.2 ⫺304.5

229.1 244.5 209.2 163.2 303.8

52.5 64.6 172.6 149.3 82.7

⫺5.5 ⫺4.8 ⫺174.8 ⫺167.9

207.0 296.1 161.0 281.6

117.9 72.7 112.3 65.6

137.9 268.6

⫺32.0 ⫺47.3

⫺479.3 ⫺443.6

⫺332.7 ⫺327.4

257.7 362.8

⫺47.4 ⫺418.0 4.0 ⫺12.3 29.9

36.3

283.8

188.7

239.3

130.6

360.5

cap height base of text

228.5 376.0 210.8 170.7 113.6 130.0 71.5

183.2 246.0

⫺441.3 ⫺445.8 ⫺460.7 ⫺56.0 ⫺420.1

80.0

376.6

133.6 228.0

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.25

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Ethyl chloroformate Ethylcyclobutane Ethylcyclohexane 1-Ethylcyclohexene Ethylcyclopentane 1-Ethylcyclopentene Ethylcyclopropane Ethyl diethylcarbamate Ethyl 2,2-dimethylpropanoate Ethylene Ethylene-d4 Ethylene carbonate Ethylenediaminetetraacetic acid Ethylenediammonium chloride 2,2⬘-(Ethylenedioxy)bisethanol Ethylene glycol dibutyl ether Ethylene glycol diethyl ether Ethylene glycol dimethyl ether Ethyleneimine Ethylene oxide Ethyl formate 2-Ethylhexanal 3-Ethylhexane 2-Ethyl-1-hexanol Ethyl hydroperoxide Ethylidenecyclohexane Ethylidenecyclopentane Ethyl isocyanide Ethyl isopropyl sulfide Ethyl lactate Ethyllithium Ethylmercury bromide Ethylmercury chloride Ethylmercury iodide 1-Ethyl-2-methylbenzene 2-Ethyl-3-methyl-1-butene Ethyl 2-methylbutanoate Ethyl 3-methylbutanoate Ethyl methyl ether 3-Ethyl-2-methylpentane 3-Ethyl-3-methylpentane 3-Ethyl-2-methyl-1-pentene

Physical State

⌬f H⬚ kJ · mol⫺1

lq g lq g lq lq g lq lq lq g g g c c

⫺505.1 ⫺27.5 ⫺211.9 ⫺171.7 ⫺106.7 ⫺163.4 ⫺19.7 ⫺24.8 ⫺592.3 ⫺577.2 ⫺536.0 52.5 38.2 ⫺581.5 ⫺1759.4

c lq

⫺513.4 ⫺804.2

lq lq lq lq g lq g lq lq lq g lq g lq lq lq lq lq c c c c g g lq lq g lq g lq g g

⫺451.4 ⫺376.6 91.9 126.5(9) ⫺78.0 ⫺52.6(6)

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

29.1 39.3

280.9 382.6

211.8 158.8

37.3

279.9

185.8

68.4 59.2

219.3 230.5

42.9 51.9 133.9

35020 259.4 193.3 178.0 ⫺11.8 ⫺13.1

⫺342.5 ⫺250.4 ⫺210.7 ⫺432.8 198.9 ⫺103.5 ⫺56.7 108.4 ⫺156.1

250.6 153.9 242.4

52.6 88.0 47.9 149.3

347.0

317.5

254 ⫺58.6 ⫺107.5 ⫺141.1 ⫺65.7 1.3 ⫺79.5 ⫺566.8 ⫺570.9 ⫺216.4 ⫺249.6 ⫺211.0 ⫺252.8 ⫺214.8 ⫺100.3

131.1

399.2

157.9

⫺117.7

309.2

93.3

21.3 19.9

441.1 433.0

short standard long

DEAN #37261

LEFT

(McGHP)

6.26

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Ethyl methyl sulfide Ethyl nitrate Ethyl nitrite 1-Ethyl-2-nitrobenzene 1-Ethyl-4-nitrobenzene Ethyl 3-oxobutanoate 3-Ethylpentane Ethyl pentanoate 2-Ethylphenol 3-Ethylphenol 4-Ethylphenol Ethylphosphonic acid Ethylphosphonic dichloride Ethyl propanoate Ethyl propyl ether Ethyl propyl sulfide 2-Ethylpyridine S-Ethyl thioacetate 2-Ethyltoluene 3-Ethyltoluene 4-Ethyltoluene N-Ethylurea Ethyl ␤-vinylacrylate Ethyl vinyl ether Ethynylbenzene Ethynylsilane Fluoranthene Fluoroacetamide Fluoroacetic acid Fluoroacetylene Fluorobenzene 2-Fluorobenzoic acid 3-Fluorobenzoic acid 4-Fluorobenzoic acid Fluoroethane 2-Fluoroethanol Fluoroethylene Fluoromethane 1-Fluoropropane 2-Fluoropropane Fluorosyltrifluoromethane 4-Fluorotoluene Fluorotribromomethane Fluorotrinitromethane Formaldehyde

Physical State lq g g g lq lq lq lq g lq lq lq c c lq lq g g lq g lq lq g g g c lq lq g g g c c c g lq g c c c g lq g g g g g lq g lq g

⌬f H⬚ kJ · mol⫺1 ⫺91.6 ⫺59.6 ⫺154.1 ⫺104.2 ⫺48.7 ⫺55.4 ⫺224.9 ⫺189.6 ⫺553.0 ⫺214.3 ⫺224.4 ⫺1051.4 ⫺613.4 ⫺502.7 ⫺463.3 ⫺272.2 ⫺144.8 ⫺104.7 7.4 ⫺268.2 1.3 ⫺1.8 ⫺3.2 ⫺357.8 ⫺338.1 ⫺167.4 ⫺140.8 327.3 189.9 ⫺496.6 ⫺688.3 ⫺150.6 ⫺116.0 ⫺567.6 ⫺582.0 ⫺585.7 ⫺263.2 ⫺465.7 ⫺138.8 ⫺237.8 ⫺285.9 ⫺293.5 ⫺766.0 ⫺186.9 ⫺190.4 ⫺220.9 ⫺108.6

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

11.4 ⫺36.9

239.1 333.1 348.3 103.5

144.6 95.1 97.4 99.2

314.5 411.5

248.0 219.6 166.0

11.0

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

⫺208.8 206.9

196.1 ⫺323.7

23.6

295.0 309.5 414.1

197.2 198.4 139.3

131.1 126.4 85.3

399.2 404.2 398.9

157.9 152.2 151.5

361.8 345.6

321.7 269.4 230.5

114.9 72.6 230.2

⫺69.0

269.4 205.9 302.6

72.6 146.4 94.4

⫺211.0

264.5

58.6

⫺213.8 ⫺200.3 ⫺204.2 ⫺707.0 ⫺79.8 ⫺193.1

222.8 304.2 292.1 322.4 237.1 345.8

37.5 82.6 82.0 79.4 171.2

⫺102.5

218.8

35.4

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.27

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Formamide Formanilide Formic acid Formyl fluoride D-(⫺)-Fructose D-(⫹)-Fucose Fullerene-C60 Fumaric acid Fumaronitrile Furan

2-Furancarboxaldehyde 2-Furancarboxylic acid 2-Furanmethanol Furfuryl alcohol Furylacrylic acid Furylethylene D-(⫹)-Galactose D-Gluconic acid D-(⫹)-Glucose D-(⫺)-Glutamic acid L-(⫹)-Glutamic acid L-Glutamine Glutaric acid Glyceraldehyde Glycerol Glyceryl 1-acetate Glyceryl 1-benzoate Glyceryl 2-benzoate Glyceryl 1,3-diacetate Glyceryl 1-dodecanoate Glyceryl 2-dodecanoate Glyceryl 1-hexadecanoate Glyceryl 1-hexanoate Glyceryl 2-hexanoate Glyceryl 1-octadecanoate Glyceryl 1-tetradecanoate Glyceryl triacetate Glyceryl trinitrate Glyceryl tris(dodecanoate) Glyceryl tris(tetradecanoate) Glycine ionized; std. state ⫹ H3NCH2COOH; std. state Glycylglycine Glyoxal Glyoxime Glyoxylic acid Guanidine

Physical State lq g c lq g g c c c c c lq g lq c lq lq c lq c c c c c c c lq lq lq c c lq c c c c c c c lq lq c c c aq aq c g c c c

⌬f H⬚ kJ · mol⫺1 ⫺254.0 ⫺193.9 ⫺151.5 ⫺424.7 ⫺378.7 ⫺376.6 ⫺1265.6 ⫺1099.1 2327.0 ⫺811.7 268.2 ⫺62.3 ⫺34.9 ⫺201.6 ⫺498.4 ⫺276.2 ⫺276.2 ⫺459.0 ⫺10.5 ⫺1286.3 ⫺1587.0 ⫺1273.3 ⫺1009.7 ⫺1005.2 ⫺826.4 ⫺960.0 ⫺598.0 ⫺668.5 ⫺909.1 ⫺777.3 ⫺772.8 ⫺1120.7 ⫺1160.9 ⫺1152.6 ⫺1281.5 ⫺1109.0 ⫺1095.8 ⫺1324.8 ⫺1222.6 ⫺1330.8 ⫺370.9 ⫺2046.0 ⫺2176.0 ⫺528.5 ⫺469.8 ⫺517.9 ⫺747.7 ⫺212.0 ⫺90.5 ⫺835.5 ⫺56.0

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺141.0

248.6

⫺361.4 ⫺351.0 ⫺368.1

129.0 248.7 246.5(8)

2302.0 ⫺655.6

426.0 168.0

520.0 142.0

0.88

177.0 267.2

114.8 65.4 163.2

⫺154.2

215.5

204.0 204.0

⫺918.8

205.4

⫺910.4 ⫺727.5 ⫺731.3

212.1 191.2 188.2

⫺477.0

206.3

218.9

⫺368.6 ⫺315.0 ⫺384.2 ⫺490.6

103.5 111.0 190.2 190.0

99.2

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 107.6 45.4 99.5 45.2 40.0

short standard long

DEAN #37261

LEFT

(McGHP)

6.28

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Guanidine carbonate Guanidine nitrate Guanidine sulfate Guanine Guanylurea nitrate L-Gulonic acid-␥-lactone Heptadecane Heptadecanoic acid 1-Heptadecene Heptanal Heptane Heptanedioic acid Heptanenitrile 1-Heptanethiol Heptanoic acid 1-Heptanol 2-Heptanone 1-Heptene cis-2-Heptene trans-2-Heptene cis-3-Heptene trans-3-Heptene 1-Heptyne Hexabromoethane Hexachlorobenzene Hexachloroethane Hexadecafluoroethylcyclohexane Hexadecafluoroheptane Hexadecane Hexadecanoic acid 1-Hexadecanol 1-Hexadecene 1,5-Hexadiene 2,4-Hexadienoic acid 1,5-Hexadiyne Hexafluoroacetone Hexafluoroacetylacetone Hexafluorobenzene Hexafluoroethane cis-Hexahydroindane

Physical State

⌬f H⬚ kJ · mol⫺1 ⫺971.9 ⫺387.0 ⫺1205.0 ⫺183.9 ⫺427.2 ⫺1219.6 ⫺393.9 ⫺924.4 ⫺268.4 ⫺311.5 ⫺264.0 ⫺224.2 ⫺187.7 ⫺1009.4 ⫺82.8 ⫺150.0 ⫺610.2 ⫺403.3 ⫺336.4

c c c c c c g c g lq g lq g c lq g lq lq g lq lq g lq lq lq lq g g c g c g lq

⫺127.6 ⫺35.5 ⫺202.8 ⫺143.6 ⫺3420.0

lq lq g c c lq lq g lq c lq g c lq g g g

⫺3420.8 ⫺456.1 ⫺374.8 ⫺891.5 ⫺686.7 ⫺635.4 ⫺328.7 ⫺248.5 54.1 ⫺390.8 384.2 ⫺1249.3 ⫺2286.7 ⫺991.3 ⫺955.4 ⫺1344.2 ⫺127.2

⫺97.9 ⫺62.3 ⫺105.1 ⫺109.5 ⫺104.3 ⫺109.3 103.0

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺557.4

295.4

47.4

160.3

82.1

817.3

179.9 ⫺100.6 ⫺86.7

813.1 335.4 461.7

8.0

427.9

36.2

493.3

⫺142.3 ⫺120.9

320.1 480.3

95.8

327.6 423.6

186.9 265.4 272.1 178.7 232.6 211.8 155.2

⫺54.9

407.7 441.9 260.2 441.2 237.3 398.7

151.1 139.3 201.3 173.2 198.2 136.7

⫺3093.0

561.8

83.7 ⫺316.1 ⫺98.7 ⫺96.6 171.5

778.3 452.4 451.9 606.7 587.9 774.1

419.0 501.6 371.8 460.7 422.0

⫺79.4 ⫺1255.8

280.8 383.2 332.3

226.7 1.1 44.2

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 258.9

394.7 475.7 383.9 230.1 224.9 166.0

488.9 361.0

156.6 106.7

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.29

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance trans-Hexahydroindane Hexamethylbenzene 1,1,1,3,3,3-Hexamethyldisilazane Hexamethyldisiloxane Hexamethylenetetramine Hexamethylphosphoric triamide Hexanal Hexanamide Hexane 1,6-Hexanedioic acid 1,2-Hexandediol 1,6-Hexanediol Hexanedinitrile 1-Hexanethiol Hexanoic acid 1-Hexanol 2-Hexanol 3-Hexanol 2-Hexanone 3-Hexanone 1-Hexene cis-2-Hexene trans-2-Hexene cis-3-Hexene trans-3-Hexene Hexyl acetate 1-Hexyne (⫺)-Histidine Hydantoin Hydrazine Hydrazinecarbothioamide Hydrazobenzene Hydroxyacetic acid 2⬘-Hydroxyacetophenone 3⬘-Hydroxyacetophenone 4⬘-Hydroxyacetophenone 2-Hydroxybenzaldehyde 2-Hydroxybenzaldoxime 2-Hydroxybenzoic acid 3-Hydroxybenzoic acid 4-Hydroxybenzoic acid

Physical State

⌬f H⬚ kJ · mol⫺1

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

g c lq

⫺131.4 ⫺162.4 ⫺518.0

117.4

306.3

245.6

lq g c lq g c lq lq g lq lq c lq g lq lq g lq lq lq lq lq g lq g lq g lq g lq lq g g c c lq c c c c c c lq c c c c

⫺814.6 ⫺777.7 125.5

⫺541.8 ⫺534.5 434.8

433.8 535.0 163.4

311.4 238.5

⫺248.4 ⫺423.0 ⫺397.0 ⫺198.8 ⫺167.1(8) ⫺985.4 ⫺577.1 ⫺569.9 85.1 ⫺129.9 ⫺583.9 ⫺377.5 ⫺317.6 ⫺392.9 ⫺392.4 ⫺322.0 ⫺320.2 ⫺74.1 ⫺43.5 ⫺83.9 ⫺52.3 ⫺85.5 ⫺53.9 ⫺79.0 ⫺47.6 ⫺86.1

⫺100.1

422.9

⫺3.8 ⫺0.25 ⫺207.3

296.1 388.4

⫺54.4 123.6 ⫺466.7 ⫺448.5 50.6 24.7 221.3 ⫺663.6 ⫺357.7 370.7 ⫺364.4 ⫺279.9 ⫺183.7 ⫺589.9 ⫺584.9 ⫺584.5

top of rh base of rh

321 148.2

195.6 143.1 232.2

27.8

454.3

⫺152.3 ⫺135.6

287.4 441.4

128.7 164.1 225.0 240.4 155.6

83.6 84.45

305.3 295.1 384.6

286.2 213.3 216.9 183.3 132.3

76.2

386.5

125.7

76.4

380.6

132.4

83.0

379.6

123.6

77.6 218.6

374.8 368.7

282.8 132.8 128.2

149.2

121.2

98.9

⫺421.3 ⫺417.3 ⫺416.5

178.2 177.0 175.7

159.1 157.3 155.1

short standard long

DEAN #37261

LEFT

(McGHP)

6.30

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance (⫾)-2-Hydroxybutanoic acid 2-Hydroxy-2,4,6-cycloheptatrienone 2-Hydroxyisobutanoic acid 2-Hydroxy-1-isopropyl-4methylbenzene 3-Hydroxy-4-methoxybenzaldehyde 4-Hydroxy-4-methyl-2pentanone 2-Hydroxymethyl-1,3-propanediol 3-Hydroxy-2-naphthalenecarboxylic acid 5-Hydroxy-1-pentanal trans-(⫺)-4-Hydroxyproline (S)-2-Hydroxypropanoic acid 2-Hydroxypropanonitrile 2-Hydroxypyridine 3-Hydroxypyridine 4-Hydroxypyridine 8-Hydroxyquinoline (⫺)-2-Hydroxysuccinic acid (⫾)-2-Hydroxysuccinic acid Hypoxanthene Icosane Icosanoic acid Icosene Imidazole Iminodiacetic acid Indane 1H-Indazole Indene 1H-Indole Indole-2,3-dione Iodoacetone Iodobenzene 2-Iodobenzoic acid 3-Iodobenzoic acid 4-Iodobenzoic acid Iodocyclohexane Iodoethane Iodoethylene Iodomethane 2-Iodo-2-methylpropane 1-Iodonaphthalene 2-Iodonaphthalene 2-Iodophenol 3-Iodophenol

Physical State

⌬f H⬚ kJ · mol⫺1

lq c

⫺679.1 ⫺239.2

c c

⫺744.3 ⫺309.6

c

⫺453.6

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

lq

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

221.3

c

⫺744.6

c

⫺547.7

lq c c lq c c c c c c c g c g c c lq c lq c c g lq g c c c lq lq g g g lq g lq c c c

⫺479.9 ⫺661.1 ⫺694.0 ⫺138.9 ⫺166.3 ⫺132.0 ⫺144.6 ⫺81.2 ⫺1103.7 ⫺1105.7 ⫺110.8 ⫺455.8 ⫺1011.9 ⫺330.2 49.8 ⫺932.6 11.5 151.9 110.6 86.7 ⫺268.2 ⫺130.5 117.1 164.9 ⫺302.3 ⫺316.9 ⫺316.1 ⫺97.2 ⫺40.0 ⫺8.1 14.4 ⫺107.5 ⫺72.0 161.5 144.3 ⫺95.8 ⫺94.5

34.3

⫺884.7 76.9 117.3

145.6 934.1

205.1

929.9

134.5 463.3 545.1 452.5

150.8

56.0

190.3

217.6

215.3

186.9

187.8

205.4 334.1

158.7 100.8

15.6

211.7 306.0 285.0 254.1

23.6

342.2

115.1 66.9 57.9 44.1 162.3 118.3

14.7 l9.2

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.31

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 4-Iodophenol 1-Iodopropane 2-Iodopropane 3-Iodopropanoic acid 3-Iodo-1-propene ␣-Iodotoluene 3-Iodotoluene 4-Iodotoluene Isobutanenitrile Isobutylamine Isobutylbenzene Isobutyl trichloroacetate Isocyanomethane (⫺)-Isoleucine (⫾)-Isoleucine Isoxazole Isopropenyl acetate Isopropyl acetate Isopropylamine Isopropylbenzene 1-Isopropyl-2-methylbenzene 1-Isopropyl-3-methylbenzene 1-Isopropyl-4-methylbenzene Isopropyl methyl ether 2-Isopropyl-5-methylphenol Isopropyl methyl sulfide Isopropyl nitrate 2-Isopropylphenol 3-Isopropylphenol 4-Isopropylphenol Isopropyl thioacetate Isopropyl trichloroacetate Isoquinoline Ketene (⫹)-Lactic acid (⫾)-Lactic acid ␤-Lactose (⫹)-Leucine (⫺)-Leucine (⫹)-Limonene (⫾)-Lysine Malic acid Maleic anhydride (R)-Malic acid (S)-Malic acid

Physical State c lq g lq g c g lq lq lq g lq lq lq g c c g lq lq lq g lq g lq lq lq lq g c lq g g lq lq lq lq lq c lq g c lq c c c lq c c c c c

⌬f H⬚ kJ · mol⫺1 ⫺95.4 ⫺66.0 ⫺30.0 ⫺74.8 ⫺40.3 ⫺460.0 91.5 57.7 79.1 67.4 25.4 ⫺132.6 ⫺69.8 ⫺553.4 163.5 ⫺637.9 ⫺635.3 78.6 ⫺386.4 ⫺518.9 ⫺112.3 ⫺83.7 ⫺41.1 4.0 ⫺73.3 ⫺78.6 ⫺78.0 ⫺278.8 ⫺252.0 ⫺309.7 ⫺105.7 ⫺90.5 ⫺191.0 ⫺233.7 ⫺252.5 ⫺265.9 ⫺298.2 ⫺536.0 144.5 ⫺47.5 ⫺694.1 ⫺674.5 ⫺2236.7 ⫺637.3 ⫺637.4 ⫺54.5 ⫺678.6 ⫺789.4 ⫺469.8 ⫺1105.7 ⫺1103.6

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 126.8 91.0 90.1

20.1

324.5

103.6

313.3

96.4 183.2

165.7 ⫺347.2

246.9 208.0

52.9 188.3

32.2 124.3 137.0

218.3 312.2 279.8 388.6

199.4 163.8 97.5 210.7 151.7

⫺120.9

306.6 253.8 332.3

161.9 111.1

13.4 ⫺40.7

263.1 359.3 373.2

172.4 117.2 120.7

⫺48.3 ⫺522.9 ⫺518.2 ⫺1567.0 ⫺347.2 ⫺346.3

247.6 142.3 192.1 386.2 208.0 211.8

⫺625.1

160.8

119.1

196.8 51.8

201.0 249.0 137.0

short standard long

DEAN #37261

LEFT

(McGHP)

6.32

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Malonamide Malonic acid Malonodiamide Malononitrile D-(⫹)-Maltose (⫾)-Mandelic acid (⫹)-Mannitol D-(⫹)-Mannose 2-Mercaptopropanoic acid Methane Methane-d4 Methanethiol Methanol (⫺)-Methionine 2-Methoxybenzaldehyde 3-Methoxybenzaldehyde 4-Methoxybenzaldehyde Methoxybenzene 2-Methoxybenzoic acid 3-Methoxybenzoic acid 4-Methoxybenzoic acid 2-Methoxyethanol 2-Methyoxyethyl acetate 2-Methoxytetrahydropyran 5-Methoxytetrazole 1-Methoxy-2,4,6-trinitrobenzene Methyl (CH3) Methyl acetate Methyl acrylate Methylamine N-Methylaniline o-Methylaniline m-Methylaniline p-Methylaniline Methyl benzoate 2-Methylbenzoic acid 3-Methylbenzoic acid 4-Methylbenzoic acid

Physical State

⌬f H⬚ kJ · mol⫺1

c c c c c c c c lq g g lq g lq g c c lq lq lq g c c c lq lq lq c c

⫺546.0 ⫺891.0 ⫺546.1 186.6 ⫺2220.9 ⫺579.4 ⫺1337.1 ⫺1263.0 ⫺468.2 ⫺74.6 ⫺88.2 ⫺46.7 ⫺22.9 ⫺239.1 ⫺201.0 ⫺577.5 ⫺266.5 ⫺276.1 ⫺267.2 ⫺114.8 ⫺67.9 ⫺538.5 ⫺553.5 ⫺561.7

g lq g lq g lq g lq lq g lq g lq g lq c lq c lq c lq

145.7 ⫺445.8 ⫺413.3 ⫺362.2 ⫺333.0 ⫺47.2 ⫺22.5 32.2 ⫺6.3 56.4 ⫺8.1 54.6 ⫺23.5 55.3 ⫺343.5 ⫺416.5

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

⫺1726.3 ⫺942.2

238.5

⫺343.9 ⫺50.5 ⫺59.5 ⫺7.7 ⫺9.9 ⫺166.6 ⫺162.3 ⫺505.8

228.9 186.3 198.9 169.2 255.1 126.8 239.9 231.5

35.7 40.3 90.5 50.3 81.2 44.1

199.0

171.1 310.0 ⫺442.3 69.1 ⫺157.5 147.9 ⫺243.2 ⫺237.6 35.7 32.7

194.2 324.4 239.5 150.2 242.9

167.6

351.0

165.4

352.5

167.7

347.0

38.7 141.9 86.0 158.8 102.1 50.1 207.1 209.6 130.2 227.0 125.5 126.2 221.3 174.9

⫺426.1 163.6 ⫺429.2 169.0

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.33

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 2-Methylbenzoic anhydride 4-Methylbenzoic anhydride 1-Methylbicyclo[4.1.0]heptane 1-Methylbicyclo[3.1.0]hexane 2-Methylbiphenyl 3-Methylbiphenyl 4-Methylbiphenyl 2-Methyl-1,3-butadiene 3-Methyl-1,2-butadiene 2-Methylbutane 2-Methyl-2-butanethiol 3-Methyl-1-butanethiol 3-Methyl-2-butanethiol 2-Methylbutanoic acid 3-Methylbutanoic acid 2-Methyl-1-butanol 3-Methyl-1-butanol 2-Methyl-2-butanol (⫾)-3-Methyl-2-butanol 3-Methyl-2-butanone 2-Methyl-1-butene 3-Methyl-1-butene 2-Methyl-2-butene trans-2-Methyl-2-butenedioic acid [also cis] cis-2-Methyl-2-butenoic acid trans-2-Methyl-2-butenoic acid 3-Methylbutyl acetate 3-Methyl-1-butyne Methyl trans-2-butenoate Methylcyclobutane Methylcyclobutanecarboxylic acid Methylcyclohexane cis-2-Methylcyclohexanol trans-2-Methylcyclohexanol cis-3-Methylcyclohexanol trans-3-Methylcyclohexanol cis-4-Methylcyclohexanol trans-4-Methylcyclohexanol 2-Methylcyclohexene Methylcyclopentane

Physical State

⌬f H⬚ kJ · mol⫺1

c c lq lq lq lq c lq g g lq g lq g g lq lq lq lq lq lq lq lq g lq g lq g lq g c

⫺533.5 ⫺520.9 ⫺59.9 ⫺33.2 108.0 85.4 55.2 48.2 75.5 129.7 ⫺178.4 ⫺154.0 ⫺162.8 ⫺127.1 ⫺114.9 ⫺158.8 ⫺554.4 ⫺561.6 ⫺356.6 ⫺356.4 ⫺379.5 ⫺366.6 ⫺299.5 ⫺262.5 ⫺61.1 ⫺35.3 ⫺51.5 ⫺27.6 ⫺68.6 ⫺41.8 ⫺824.4

c c lq g lq lq lq

⫺455.6 ⫺490.8

lq g lq lq lq lq lq lq lq lq g

⌬f G⬚ kJ · mol⫺1

145.9 198.6 ⫺14.8 9.2

S⬚ J · deg⫺1 · mol⫺1

229.3 315.6 319.7 260.4 343.6 290.1 386.9

152.6 104.6 105.4 164.8 118.8 198.1 143.5

268.5

59.7

254.0 339.5 253.3 333.5 251.0 338.6

157.2 110.0 156.1 118.6 152.8 105.0

136.4 ⫺382.8 ⫺44.5 ⫺395.0

205.5

319.0

248.5 104.7

⫺190.1 ⫺154.7 ⫺390.2 ⫺415.8 ⫺416.1 ⫺394.4 ⫺413.2 ⫺433.3 ⫺81.2 ⫺138.0 ⫺106.2

20.3 27.3

247.9 343.3

184.9 135.0 20017 20017 29217 20217 20217 20217

31.5 35.8

247.9 339.9

158.7 109.8

65.6 74.8

229.3

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

197.1 220.1 210.0 247.1 232.2 179.9

⫺175.3

top of rh base of rh

short standard long

DEAN #37261

LEFT

(McGHP)

6.34

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 1-Methylcyclopentanol 2-Methylcyclopentanone 1-Methylcyclopentene 3-Methylcyclopentene 4-Methylcyclopentene 1-Methylcyclopropene Methylenecyclobutane Methylenebutanedioic acid Methylenecyclohexane Methylenecyclohexene Methylenecyclopropane Methyl decanoate Methyl 2,2-dimethylpropanoate 2-Methyl-1,3-dioxane 4-Methyl-1,3-dioxane N-Methyldiphenylamine 4-Methyldiphenylamine Methyl dodecanoate Methylene (CH2) Methylenebutanedioic acid Methylenecyclohexane 2-Methylenecyclohexanol 3-Methylenecyclohexene 2-Methylenecyclopentanol Methylenecyclopropane Methylenesuccinic acid Methylene sulfate N-Methylformamide Methyl formate Methyl 2-furancarboxylate 2-Methyl-2,5-furandione ␣-Methyl-(⫹)-glucoside N-Methylglycine Methylglyoxal Methylglyoxime 2-Methylheptane 3-Methylheptane 4-Methylheptane Methyl heptanoate 2-Methylhexane 3-Methylhexane Methyl hexanoate 5-Methyl-1-hexene cis-3-Methyl-3-hexene

Physical State lq lq g g g lq g g c lq lq g lq lq lq c lq c lq g c lq lq lq lq g c c lq lq g lq lq c c g c lq g lq g lq g lq lq g lq g lq g g

⌬f H⬚ kJ · mol⫺1 ⫺343.3 ⫺265.3 ⫺3.8 7.4 14.6 1.7 243.6 121.6 ⫺841.1 ⫺61.3 ⫺12.7 200.5 ⫺640.4 ⫺530.0 ⫺436.4 416.1 120.5 49.0 ⫺693.0 390.4 ⫺841.1 ⫺61.3 ⫺277.6 ⫺12.7 46.9 200.5 ⫺841.2 ⫺688.7 ⫺386.1 ⫺357.4 ⫺450.0 ⫺504.5 ⫺1233.4 ⫺513.3 ⫺27.1 ⫺126.8 ⫺255.0 ⫺215.4 ⫺252.3 ⫺212.5 ⫺251.6 ⫺212.0 ⫺567.1 ⫺229.5 ⫺194.6 ⫺226.4 ⫺192.3 ⫺540.2 ⫺65.7 ⫺79.4

⌬f G⬚ kJ · mol⫺1

102.1 115.0 121.6

S⬚ J · deg⫺1 · mol⫺1

326.4 330.5 328.9

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

100.8 100.0 100.0

257.9

372.9

⫺297.2

194.9

33.8

285.3

123.8 119.1 64.4

13.7

356.4 452.5 362.6 461.6

16.7

453.3

3.2

323.3 420.0

4.6

424.1

12.8

252.0 250.2 251.1 285.1 222.9 166.0 214.2 166.0

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.35

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance trans-3-Methyl-3-hexene Methylhydrazine 2-Methyl-1H-indole 3-Methyl-1H-indole Methyl isocyanate Methyl isocyanide 1-Methyl-4-isopropylbenzene Methyl isopropyl sulfide Methyl isothiocyanate 5-Methylisoxazole Methylmercury bromide Methylmercury chloride Methylmercury iodide Methyl 2-methylbutanoate Methyl 3-methylbutanoate 7-Methyl-3-methylene-1,6octadiene (R)-1-Methyl-4-(1-methylethenyl)cyclohexene 1-Methylnaphthalene 2-Methylnaphthalene Methyl nitrate Methyl nitrite Methyl nitroacetate 2-Methyl-5-nitroaniline 4-Methyl-3-nitroaniline 1-Methyl-2-nitrobenzene 1-Methyl-3-nitrobenzene 1-Methyl-4-nitrobenzene 2-Methyl-2-nitropropane 2-Methyl-2-nitro-1,3propanediol 2-Methyl-2-nitro-1-propanol 2-Methylnonane 5-Methylnonane Methyl phenylcarbamate Methyl cis-9-octadecanoate Methyl octanoate 2-Methyl-2-oxazoline 2-Methylpentane 3-Methylpentane 2-Methyl-2,4-pentanediol Methyl pentanoate 2-Methyl-1-pentanol 2-Methyl-3-pentanol

Physical State

⌬f H⬚ kJ · mol⫺1

g lq g c c lq g lq g c g lq c c c lq lq lq

⫺76.8 54.2 94.7 60.7 68.2 ⫺92.0 163.5 ⫺78.0 ⫺90.4 79.4 131.0 ⫺5.6 ⫺86.2 ⫺116.3 ⫺43.5 ⫺534.3 ⫺538.9 14.5

lq

⫺54.5

lq c g lq g g lq c c lq lq c c c

56.3 44.9 106.7 ⫺156.3 ⫺124.4 ⫺66.1 ⫺464.0 ⫺91.3 ⫺71.7 ⫺9.7 ⫺31.5 ⫺48.1 ⫺229.8 ⫺575.3

c lq lq c lq lq g lq g lq g lq lq lq lq

⫺410.0 ⫺309.8 ⫺307.9 ⫺186.7 ⫺734.5 ⫺590.3 ⫺130.5 ⫺204.6 ⫺174.8 ⫺202.4 ⫺172.1 ⫺514.2 ⫺396.4

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

179.9 186.9

165.9 278.7

134.9 71.1

165.7

246.8

13.4

359.3

52.9 236.4 117.2

144.4

252.3

65.5

24920 189.4 192.6 216.2 ⫺43.5 ⫺39.3 1.0

⫺5.0 2.1

254.8 220.0 380.0 217.2 318.5 284.3

224.4 196.0 159.8 157.3 76.5 63.2

420.1 423.8

313.3 314.4

290.6 380.5 292.5 379.8

193.7 144.2 190.7 143.1 236.0 229.3 248.0

short standard long

DEAN #37261

LEFT

(McGHP)

6.36

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 3-Methyl-2-pentanol 3-Methyl-3-pentanol 4-Methyl-2-pentanol 2-Methyl-3-pentanone 4-Methyl-2-pentanone 2-Methyl-1-pentene 2-Methyl-2-pentene 3-Methyl-1-pentene cis-3-Methyl-2-pentene trans-3-Methyl-2-pentene 4-Methyl-1-pentene cis-4-Methyl-2-pentene trans-4-Methyl-2-pentene Methyl 2-methylpropenoate 4-Methyl-3-penten-2-one Methyl pentyl sulfide 3-Methyl-1-phenyl-1-butanone Methyl phenyl sulfide Methyl phenyl sulfone Methylphosphonic acid (⫾)-2-Methylpiperidine 2-Methylpropanal N-Methylpropanamide 2-Methylpropanamine 2-Methylpropane 2-Methyl-1,2-propanediamine 2-Methyl-1,2-propanediol 2-Methylpropanenitrile 2-Methyl-1-propanethiol 2-Methyl-2-propanethiol 2-Methylpropanoic acid 2-Methyl-1-propanol 2-Methyl-2-propanol 2-Methylpropene 2-Methylpropenoic acid 1-Methyl-2-propylbenzene 1-Methyl-3-propylbenzene 1-Methyl-4-propylbenzene (2-Methylpropyl)benzene Methyl propyl ether Methyl propyl sulfide 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 1-Methyl-1H-pyrrole

Physical State lq lq lq lq lq g g g g g g g g lq lq g lq lq c c lq lq g lq lq g lq lq lq g g lq lq g lq g g lq lq lq lq lq lq g g lq g lq g lq lq

⌬f H⬚ kJ · mol⫺1

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1 275.9 293.4 273.0

⫺394.7 ⫺325.9 ⫺59.4 ⫺66.9 ⫺49.5 ⫺62.3 ⫺63.1 ⫺51.3 ⫺57.5 ⫺61.5

77.6 71.2 86.4 73.2 71.3 90.0 82.1 79.6

382.2 378.4 376.8 378.4 381.8 367.7 373.3 368.3

122.9 ⫺220.2 43.0 ⫺345.4 ⫺1054 ⫺124.9 ⫺247.4 ⫺215.8

35.1

450.7

213.3 135.6 126.6 142.4 126.6 126.6 126.5 133.6 141.4 191.2 212.5 163.7

⫺20.9

294.6

179 183.2 130.5⫺12

5.6 0.7

362.9 338.0

⫺132.6 ⫺134.2 ⫺133.9 ⫺539.7 ⫺13.8 ⫺97.3 ⫺109.6 ⫺334.7 ⫺283.9 ⫺359.2 ⫺312.5 ⫺16.9 ⫺72.5 ⫺76.2 ⫺75.1 ⫺69.8 ⫺266.0 ⫺238.2 ⫺82.3 56.7 99.2 61.9 106.4 59.2 62.4

cap height base of text

⫺167.35 ⫺177.7 58.1

⫺109.9 18.4 166.5 177.1 214.0 184.3

214.7 359.0 193.3 326.7 293.6

262.9 349.5 371.7 217.9 325.0 216.3 325.0 209.1

118.3 121.0 173 181.2 111.3 219.8 113.6 89.1 161.1

240.6 165.4 112.5 117.4 158.4 100.0 158.7 99.6 159.0

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.37

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 2-Methyl-1H-pyrrole 3-Methyl-1H-pyrrole N-Methylpyrrolidone 2-Methylquinoline Methyl salicylate Methylsilane ␣-Methylstyrene cis-(␤)-Methylstyrene trans-(␤)-Methylstyrene Methylsuccinic acid Methylsuccinic anhydride Methyl tetradecanoate 2-Methylthiacyclopentane 4-Methylthiazole Methylthiirane 2-Methylthiophene 3-Methylthiophene Methyl p-tolyl sulfone 5-Methyluracil Methylurea Morphine monohydrate Morpholine Murexide Naphthalene 1-Naphthaleneacetic acid 2-Naphthaleneacetic acid 1-Naphthoic acid 2-Naphthoic acid 1-Naphthol 2-Naphthol 1,4-Naphthoquinone 1-Naphthyl acetate 2-Naphthyl acetate 1-Naphthylamine 2-Naphthylamine Nicotine Nitrilotriacetic acid Nitroacetone 2-Nitroaniline 3-Nitroaniline 4-Nitroaniline Nitrobenzene 2-Nitrobenzoic acid 3-Nitrobenzoic acid 4-Nitrobenzoic acid 3-Nitrobiphenyl 4-Nitrobiphenyl 1-Nitrobutane

Physical State lq lq lq c lq g g g g c lq lq g lq g lq g lq g c c c c lq c c g c c c c c lq c c c c c lq c lq c c c lq c c c c c g

⌬f H⬚ kJ · mol⫺1

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

23.3 20.5 ⫺262.2 164.4 ⫺531.8 113.0 121.3 117.2 ⫺958.2 ⫺617.6 ⫺743.9 ⫺63.3 68.0 45.8 44.6 83.5 43.1 82.6 ⫺372.8 ⫺462.8 ⫺332.8 ⫺711.7

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

307.8

208.5 216.9 213.7

256.5 383.7 383.7 380.3

249.0 65.9 145.2 145.2 146.0

122.9

320.6

149.8 95.4

121.8

321.3

94.9

164.8 ⫺1212.1 77.9 150.6 ⫺359.2 ⫺371.9 333.5 ⫺346.1 ⫺121.0 ⫺124.2 ⫺183.4 ⫺288.2 ⫺304.3 67.8 59.7 39.3 ⫺1311.9 ⫺278.6 ⫺26.1 ⫺38.3 ⫺42.0 12.5 ⫺378.5 ⫺394.7 ⫺392.2 65.1 40.5 ⫺143.9

201.6 224.1

167.4 333.1

165.7 131.9

166.9

⫺1307.5 178.2 174.1 151.0 146.2 ⫺196.4 ⫺220.5 ⫺222.0

176.2 176.2 176.2 224.3 208.4 205.0 210.0

166.0 158.8 167.0 185.8

10.1

394.5

124.9

181.2

short standard long

DEAN #37261

LEFT

(McGHP)

6.38

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 2-Nitrobutane 3-Nitro-2-butanol N-Nitrodiethylamine 2-Nitrodiphenylamine Nitroethane 2-Nitroethanol 2-Nitrofuran 5-Nitrofurancarboxylic acid 1-Nitroguanidine Nitromethane (Nitromethyl)benzene 1-Nitronaphthalene 1-Nitroso-2-naphthol 2-Nitroso-1-naphthol 4-Nitroso-1-naphthol 1-Nitropropane 2-Nitropropane 1-Nitro-2-propanone 4-Nitrosodiphenylamine ␤-Nitrostyrene 4-Nitrotoluene Nonadecane 1-Nonadecene 1-Nonanal Nonane 1-Nonanethiol Nonanoic acid 1-Nonanol 2-Nonanone 5-Nonanone 1-Nonene Norleucine Octadecane Octadecanoic acid 1,8-Octadecanoic acid 1-Octadecene cis-9-Octadecenoic acid trans-9-Octadecenoic acid 1,7-Octadiyne Octafluorocyclobutane Octafluoropropane Octafluorotoluene 1-Octanal Octanamide

Physical State g lq lq c lq g lq c c c lq g lq c c c c lq g lq g c c c c g g g lq g g lq g lq lq g c c g c c g lq c lq lq g g lq g c

⌬f H⬚ kJ · mol⫺1 ⫺163.6 ⫺390.0 ⫺106.2 64.4 ⫺143.9 ⫺102.3 ⫺350.7 ⫺104.1 ⫺516.8 ⫺92.4 ⫺113.1 ⫺74.3 ⫺22.8 42.6 ⫺50.5 ⫺61.8 ⫺107.8 ⫺167.2 ⫺123.8 ⫺180.3 ⫺139.0 ⫺294.7 213.0 30.5 ⫺48.1 ⫺435.1 ⫺309.6 ⫺310.3 ⫺274.7 ⫺228.2 ⫺190.8 ⫺659.7 ⫺376.3 ⫺397.2 ⫺398.2 ⫺103.5 ⫺639.1 ⫺567.4 ⫺414.6 ⫺947.7 ⫺1038.1 ⫺289.0 ⫺743.5 ⫺910.9 334.4 ⫺1542.6 ⫺1783.1 ⫺1311.1 ⫺289.6 ⫺473.2

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

⫺6.2

383.3

123.5

⫺4.9

315.4

134.4 78.2

⫺14.4 ⫺6.8

171.8 275.0

106.6 57.3

175.3 170.3

108.9 196.7 ⫺74.9

895.2 891.0 539.6

24.8 53.0

505.7 571.2

⫺110.5

558.6

172.3 440.4 429.7 216.8 284.4 211.7 232.7 362.4 224.3

112.7

401.4 501.5

303.6 201.0

100.5

480.2 856.2

485.6 417.6 501.5

188.3

852.0

406.8 577.050

⫺1398.8

400.4

209.8⫺6 156.2

⫺83.3

355.5 500.7

262.3 194.0

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.39

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Octane 1-Octanenitrile 1-Octanethiol Octanoic acid 1-Octanol 2-Octanol 2-Octanone 1-Octene cis-2-Octene trans-2-Octene 1-Octyne (⫾)-Ornithine Oxalic acid Oxalic acid dihydrate Oxaloyl dichloride Oxaloyl dihydrazide Oxamic acid Oxamide Oxazole 2-Oxetanone Oxindole 2-Oxohexamethyleneimine Oxomethyl (HCO) 2-Oxo-1,5-pentanedioic acid 4-Oxopentanoic acid 2-Oxopropanoic acid 8-Oxypurine Papaverine Paraformaldehyde Paraldehyde Pentachloroethane Pentachlorofluoroethane Pentachlorophenol Pentacyclo[4.2.0.02,5.03,8.04,7]octane Pentadecane Pentadecanoic acid 1-Pentadecene 1-Pentadecyne 1,2-Pentadiene cis-1,3-Pentadiene trans-1,3-Pentadiene 1,4-Pentadiene 2,3-Pentadiene Pentaerythritol Pentaerythritol tetranitrate Pentafluorobenzoic acid Pentafluoroethane

Physical State

⌬f H⬚ kJ · mol⫺1 ⫺250.1 ⫺208.6 ⫺107.3 ⫺44.9 ⫺636.0 ⫺426.5

lq g lq g lq lq lq lq lq g lq lq g c c c lq c c c g lq c c g c c lq c c c lq lq g g c c

⫺384.5 ⫺121.8 ⫺81.4 ⫺135.7 ⫺135.7 82.4 ⫺652.7 ⫺821.7 ⫺1492.0 ⫺367.6 ⫺295.2 ⫺661.2 ⫺504.4 ⫺5.5 ⫺329.9 ⫺172.4 ⫺329.4 43.1 ⫺1026.2 ⫺697.1 ⫺584.5 ⫺64.4 ⫺502.3 ⫺177.6 ⫺687.0 ⫺187.6 ⫺142.0 ⫺317.2 ⫺292.4 541.8

g c g g g g g g g c c c g

⫺352.8 ⫺861.7 ⫺227.2 ⫺61.8 140.7 81.5 76.5 105.7 133.1 ⫺920.6 ⫺538.6 ⫺1239.6 ⫺1104.6

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

254.6 188.9

466.7

44.6

582.2

⫺143.1

377.4

⫺140.3

373.8

104.2

462.5

235.4

496.6

209.8 297.9 305.1 330.1 273.3 241.0 178.1 239.0 239.0 174.0

⫺697.9

109.8

91.0

⫺342.7

118.0 175.3

122.1

⫺95.1 28.0

168.6 224.7

156.8 34.6

⫺463.4

179.5

⫺70.3 ⫺234.0 ⫺144.1

381.5 391.8 251.9

75.2

739.4

⫺1029.3

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

16.4

163.1 293.9 210.4 145.8 146.73 170.3 205.9 ⫺613.8

top of rh base of rh

173.8 118.1 202.0

735.2 719.3 333.5 324.3 319.7 333.5 324.7 198.1

349.0 443.3 338.2 33.41 105.4 94.6 103.3 105.0 101.3 190.4

333.7

95.7

short standard long

DEAN #37261

LEFT

(McGHP)

6.40

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Pentafluorophenol 2,3,4,5,6-Pentafluorotoluene Pentamethylbenzene Pentamethylbenzoic acid Pentanal Pentanamide 1-Pentanamine Pentane 1,5-Pentanediol 2,4-Pentanedione 1,5-Pentanedithiol Pentanenitrile 1-Pentanethiol Pentanoic acid 1-Pentanol 2-Pentanol 3-Pentanol 2-Pentanone 3-Pentanone 1-Pentene cis-2-Pentene trans-2-Pentene cis-2-Pentenenitrile trans-2-Pentenenitrile trans-3-Pentenenitrile 2-Pentenoic acid 3-Pentenoic acid 4-Pentenoic acid cis-3-Penten-1-yne trans-3-Penten-1-yne Pentyl acetate 1-Pentyne 2-Pentyne Perfluoropiperidine Perylene ␣-Phellandrene Phenanthrene 9,10-Phenanthrenedione Phenazine Phenol

Physical State c lq c g c g c lq lq g lq lq g g lq lq lq g lq g lq g lq g lq g lq lq g lq g lq g lq lq lq lq lq lq lq lq lq g g lq c lq c c c c

⌬f H⬚ kJ · mol⫺1 ⫺1024.1 ⫺883.8 ⫺133.6 ⫺74.5 ⫺536.1 ⫺228.5 ⫺379.5 ⫺173.5 ⫺146.9 ⫺531.5 ⫺423.8 ⫺380.6 ⫺71.0 ⫺33.1 ⫺151.3 ⫺559.4 ⫺491.9 ⫺351.6 ⫺294.7 ⫺365.2 ⫺311.0 ⫺368.9 ⫺311.4 ⫺297.3 ⫺259.0 ⫺296.5 ⫺46.0 ⫺21.2 ⫺53.7 ⫺27.6 ⫺58.2 ⫺31.9 71.8 74.9 80.9 ⫺446.4 ⫺434.8 ⫺430.6 226.5 228.2 144.4 128.9 ⫺2020.5 182.8 41.3 116.2 ⫺154.7 237.0 ⫺165.1

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1

306.4

225.8

123.3

443.9

216.5

⫺108.3

383.0

125.4

⫺9.3 ⫺8.4

262.7 349.0

397.9

cap height base of text

218.0 167.2 120.2 321.3 208.2 120.1 180

⫺357.2

259.8 439.8

210.3

⫺146.0

402.5

⫺158.2

382.0

⫺137.1

69.9

376.2 266.0 262.6 345.8 258.6 346.3 256.5 340.4

184.1 121.0 190.9 154.0 109.6 151.7 101.8 157.0 108.5

210.3 194.2 ⫺1768.5

329.8 331.8 393.4

261.0 106.7 98.7 296.8

268.3

215.1

220.6

⫺50.4

144.0

127.4

208.1 133.1

239.7

79.1 71.8

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.41

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance

Phenoxyacetic acid Phenyl acetate Phenylacetic acid Phenylacetylene (⫾)-3-Phenyl-2-alanine Phenyl benzoate Phenylboron dichloride 1-Phenylcyclohexene Phenylcyclopropane N-Phenyldiacetimide 1,3-Phenylenediamine Phenyl formate N-Phenylglycine (⫾)-2-Phenylglycine Phenylhydrazine Phenyl 2-hydroxybenzoate Phenylmethanethiol Phenylmethyl acetate N-Phenyl-2-naphthylamine 1-Phenyl-1-propanone 1-Phenyl-2-propanone 1-Phenylpyrrole 2-Phenylpyrrole Phenylsuccinic acid S-Phenyl thioacetate Phenyl vinyl ether Phosgene Phthalamide l,2-Phthalic acid l,3-Phthalic acid 1,4-Phthalic acid Phthalic anhydride Phthalonitrile Picric acid ␣-Pinene ␤-Pinene Piperazine 2,5-Piperazinedione Piperidine 2-Piperidone L-Proline Propadiene Propanal Propanamide Propane Propanediamide (⫾)-1,2-Propanediamine

Physical State lq g c lq c g c c lq lq lq c c lq c c lq c lq lq c lq lq c c c lq lq g c c c c c c c lq lq c c lq c c g lq g c lq g c lq

⌬f H⬚ kJ · mol⫺1 ⫺96.4 ⫺513.8 ⫺334.9 ⫺398.7 327.3 ⫺466.9 ⫺241.0 ⫺299.4 ⫺16.8 100.3 ⫺362.5 ⫺7.8 ⫺268.7 ⫺402.5 ⫺431.8 141.0 ⫺436.6 43.5

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1

⫺32.9

315.6

199.841 103.6

363.5 ⫺211.7

321.7 213.6

114.9 203.0

154.5

159.6

top of rh base of rh cap height base of text

217.0

148.5 159.8 ⫺167.2 ⫺151.9 154.3 139.2 ⫺841.0 ⫺122.0 ⫺26.2 ⫺220.9 ⫺433.1 ⫺782.0 ⫺803.0 ⫺816.1 ⫺460.1 280.6 ⫺214.4 ⫺16.4 ⫺7.7 ⫺45.6 ⫺446.5 ⫺86.4 ⫺306.6 515.2 190.5 ⫺215.3 ⫺185.6 ⫺338.2 ⫺103.8 ⫺546.1 ⫺97.8

⫺206.8

283.8

57.7

⫺591.6

207.9

188.3

⫺331.0

180.0

160.0

240.2

85.8

⫺112.1

210.0 164.9

202.4

243.9

⫺130.5

304.5

⫺23.4

270.2

179.9 (lq 307.8) 59.0 137.2 80.7 98.3⫺43 73.6

short standard long

DEAN #37261

LEFT

(McGHP)

6.42

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 1,2-Propanediol 1,3-Propanediol 1,2-Propanedione Propanedinitrile 1,2-Propanedithiol 1,3-Propanedithiol Propanenitrile 1-Propanethiol 2-Propanethiol 1,2,3-Propanetriol tris(acetate) Propanoic acid Propanoic anhydride 1-Propanol 2-Propanol 2-Propenal Propene trans-1-Propene-1,2dicarboxylic acid 2-Propenenitrile cis-1,2,3-Propenetricarboxylic acid trans-1,2,3-Propenetricarboxylic acid 2-Propenoic acid 2-Propen-1-ol 2-Propenyl acetate cis-1-Propenylbenzene trans-1-Propenylbenzene 2-Propenylbenzene Propyl acetate Propylamine Propylbenzene Propylcarbamate Propylchloroacetate Propylchlorocarbonate Propylcyclohexane Propylcyclopentane Propylene carbonate Propylene oxide

Physical State

⌬f H⬚ kJ · mol⫺1

lq lq lq lq lq lq lq lq g lq g lq lq lq lq g lq g g g c

⫺485.7 ⫺464.9 ⫺309.1 186.4 ⫺79.4 ⫺79.4 15.5 ⫺99.9 ⫺67.9 ⫺105.0 ⫺76.2 ⫺1330.8 ⫺510.7 ⫺679.1 ⫺302.6 ⫺255.1 ⫺318.1 ⫺272.6 ⫺85.8 20.0 ⫺824.4

lq g c

147.1 180.6 ⫺1224.7

c

⫺1233.0

lq g lq g lq g g lq lq lq g lq g c lq g lq g lq g lq lq g

⫺383.8 ⫺336.5 ⫺171.8 ⫺124.5 ⫺386.2 121.3 117.2 88.0 ⫺101.5 ⫺70.2 ⫺38.3 7.9 ⫺552.6 ⫺515.6 ⫺492.7 ⫺237.4 ⫺192.5 ⫺188.8 ⫺147.1 ⫺613.2 ⫺123.0 ⫺94.7

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 190.8

89.2

193.6 322.7 181.1 309.2

119.3 144.6 94.8 145.3 96.0 384.7 152.8 235.0 143.7 85.6 155.0 89.3

266.6

64.3

195.4

274.1

108.8 63.8

⫺286.3

315.2

⫺71.3

307.6

216.9 213.7

383.7 380.3

145.7 77.8 138.9 76.0 184.1 145.2 146.0

325.1 287.8 400.7

196.2 162.5 91.2 214.7 152.3

2.2 ⫺2.6 ⫺383.5 ⫺475.6 ⫺170.6 ⫺161.8 ⫺180.3 ⫺173.4 ⫺64.6 62.8

39.8 137.2

189.3 242.5 336.4 233.5 324.3 458.3 191.0

52.6

311.9 419.5 310.8 417.3

⫺25.8

196.5 286.9

47.3

242.0 184.2 216.8 154.6 218.6 120.4 72.6

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.43

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Propyl formate Propyl nitrate S-Propyl thioacetate Propyl trichloroacetate Propyl vinyl ether 2-Propynyl-1-amine Propyne 2-Propynoic acid 1H-Purine Pyrazine 1H-Pyrazole Pyrene Pyridazine Pyridine 3-Pyridinecarbonitrile 3-Pyridinecarboxylic acid Pyrimidine 1H-Pyrrole Pyrrole-2-carboxaldehyde Pyrrole-2-carboldoxime Pyrrolidine (⫾)-2-Pyrrolidinecarboxylic acid 2-Pyrrolidone Quinhydrone Quinidine Quinine Quinoline Raffinose L-(⫹)-Rhamnose D-(⫺)-Ribose Salicylaldehyde Salicylaldoxime Salicylic acid Semicarbazide std. state (⫺)-Serine (⫾)-Serine L-(⫺)-Sorbose 5,5⬘-Spirobis(1,3-dioxane) Spiro[2.2]pentane cis-Stilbene trans-Stilbene (⫺)-Strychnine Styrene Succinic acid Succinic acid monoamide

Physical State

⌬f H⬚ kJ · mol⫺1

lq g lq lq lq lq g lq c c c lq c lq lq g c c lq lq c c lq g c

⫺500.3 ⫺173.9 ⫺294.1 ⫺513.0 ⫺190.9 205.7 184.9 ⫺193.2 169.4 139.8 116.0 105.4 125.5 224.8 100.2 140.4 193.4 ⫺344.9 145.9 63.1 ⫺106.4 12.1 ⫺41.0 ⫺3.6 ⫺524.2

c c c c lq c c c lq c c aq c c c c lq g lq c c lq g c c

⫺286.2 ⫺82.8 ⫺160.3 ⫺155.2 141.2 ⫺3184 ⫺1073.2 ⫺1047.2 ⫺279.9 ⫺183.7 ⫺589.5 ⫺166.9 ⫺732.7 ⫺739.0 ⫺1271.5 ⫺702.1 157.5 185.2 183.3 136.9 ⫺171.5 103.8 147.9 ⫺940.5 ⫺581.2

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺27.3

385.4

171.4 121.3

194.4

248.1

60.7

224.9

229.7

177.9 282.8

132.7 78.1

156.4

127.7

114.7

204.1 309.5

156.6 81.1

⫺323.0

325.9

164.4 277.0

275.7

217.2

194.9

181.3 190.2

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

22218 ⫺418.1 ⫺40.6

178.2 297.9

⫺908.4

220.9

265.3

193.7 282.2

317.6

251.0

202.4 213.8 ⫺747.4

237.6 345.1 167.3

134.5 88.1

182.0 122.1 153.1

short standard long

DEAN #37261

LEFT

(McGHP)

6.44

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Succinic anhydride Succinimide Succinonitrile (⫹)-Sucrose (⫾)-Tartaric acid (⫺)-Tartaric acid meso-Tartaric acid ␣-Terpinene 1,1,2,2,-Tetrabromoethane Tetrabromoethylene Tetrabromomethane Tetrabutyltin Tetracene Tetrachloro-1,4-benzoquinone 1,1,2,2,-Tetrachloro-1,2difluoroethane 1,1,1,2-Tetrachloroethane 1,1,2,2,-Tetrachloroethane Tetrachloroethylene Tetrachloromethane 1,1,1,3-Tetrachloropropane 1,2,2,3-Tetrachloropropane 1,1,2,2-Tetracyanocyclopropane Tetracyanoethylene Tetracyanomethane Tetradecane Tetradecanoic acid 1-Tetradecanol 1-Tetradecene Tetraethylene glycol Tetraethylgermanium Tetraethyllead Tetraethylsilane Tetraethyltin 1,1,1,2-Tetrafluoroethane Tetrafluoroethylene Tetrafluoromethane 2,2,3,3-Tetrafluoro-1-propanol Tetrahydrofuran Tetrahydro-2-furanmethanol 1,2,3,4-Tetrahydronaphthalene 5,6,7,8-Tetrahydro-1-naphthol

Physical State c c lq c c c c g lq g c g lq c c

⌬f H⬚ kJ · mol⫺1 ⫺608.6 ⫺459.0 139.7 ⫺2226.1 ⫺1290.8 ⫺1282.4 ⫺1279.9 ⫺20.5

29.4 83.9 ⫺304.6 158.8 ⫺288.7

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺1544.7

191.6 360.2

47.7 67.0

387.1 212.5 358.1

lq

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

145.6

165.7 102.7 144.3 91.2

178.6

g lq g lq g lq g lq g lq lq c

⫺489.9

⫺407.1

382.8

⫺149.4 ⫺195.0 ⫺149.2 ⫺50.6 ⫺10.9 ⫺128.2 ⫺95.7 ⫺207.8 ⫺251.8 590

⫺80.3 ⫺95.0 ⫺85.6

355.9 246.9 362.7

3.0 ⫺62.6 ⫺53.6

266.9 216.2 309.9

c c g c c g lq lq lq lq lq g g g g lq g lq lq c

623.8 611.6 ⫺332.1 ⫺833.5 ⫺629.6 ⫺206.5 ⫺981.6 ⫺210.5 52.7

66.9

700.4

154.8

696.2

336.4

464.6

307.4 298.1

⫺826.2 ⫺623.7 ⫺888.3

316.2 300.0 261.6

86.3 80.5 61.0

204.3 302.4

124.0 76.3 181.2 217

⫺95.8 ⫺895.8 ⫺658.9 ⫺933.6 ⫺1061.3 ⫺216.2 ⫺184.2 ⫺435.6 ⫺29.2 ⫺285.3

123.4 153.8 102.7 162.3 100.8 143.4 130.7 83.4

326.1 432.0 388.0 315.3 428.8

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.45

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Tetrahydro-2H-pyran Tetrahydro-2H-pyran-2-one 1,2,3,6-Tetrahydropyridine Tetrahydrothiophene Tetrahydrothiophene-1,1dioxide Tetraiodoethylene Tetraiodomethane Tetramethylammonium bromide Tetramethylammonium chloride Tetramethylammonium iodide 1,2,3,4-Tetramethylbenzene 1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene 2,3,5,6-Tetramethylbenzoic acid 2,2,3,3-Tetramethylbutane 1,1,2,2-Tetramethylcyclopropane Tetramethyllead 2,2,3,3-Tetramethylpentane 2,2,3,4-Tetramethylpentane 2,2,4,4-Tetramethylpentane 2,3,3,4-Tetramethylpentane Tetramethylsilane Tetramethylsuccinic acid Tetramethylthiacyclopropane Tetramethyltin Tetranitromethane 1,1,1,2-Tetraphenylethane 1,1,2,2-Tetraphenylethane Tetraphenylethylene Tetraphenylhydrazine Tetraphenylmethane Tetraphenyltin Tetrapropylgermanium Tetrapropyltin 1,2,3,4-(1H)-Tetrazole Theobromine 2-Thiaadamantane Thiacyclobutane Thiacycloheptane Thiacyclohexane Thiacyclopentane Thiacyclopropane Thianthrene Thiirane

Physical State

⌬f H⬚ kJ · mol⫺1

lq lq lq lq g lq

⫺258.3 ⫺436.7 33.5 ⫺72.9 ⫺34.1

c g c c c lq lq c c c g lq

305.0 474.0 ⫺251.0 ⫺276.4 ⫺203.4 ⫺90.2 ⫺96.4 ⫺119.9 ⫺506.1 ⫺269.0 ⫺225.6 ⫺119.7

lq g lq lq lq lq lq g c c g lq c c c c c c g lq c c c g g lq g g g c g

97.9 135.9 ⫺278.3 ⫺277.7 ⫺280.0 ⫺277.9 ⫺264.0 ⫺239.1 ⫺1012.5 ⫺83.0 ⫺18.8 38.4 223.0 216.0 311.5 457.9 247.1 412.1 ⫺229.7 ⫺211.3 237.0 ⫺361.5 ⫺143.5 60.6 ⫺61.3 ⫺106.3 ⫺63.5 ⫺33.8 82.2 ⫺182.5 82.0

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 156.5

⫺45.8

309.6

92.5 18020

217.1

391.9

95.9

106.7 98.7 101.3

290.6 416.5 245.6

240.7 215.1

22.0

273.7 389.4

239.2 192.5

262.8 270.7

320.1 420.5

144.0 271.5 266.3

359.1

204.1 143.9

53.1 46.0 96.9

285.0 361.9 218.2 323.0 309.4 255.3

68.3 124.6 163.3 109.7 90.9 53.7

96.8

255.2

53.3

⫺100.0

574.0

107.1 84.1

short standard long

DEAN #37261

LEFT

(McGHP)

6.46

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Thiirene Thioacetamide Thioacetic acid 1,2-Thiocresol Thiohydantoic acid Thiohydantoin 2-Thiolactic acid Thiophene Thiophenol Thiosemicarbazide Thiourea (⫺)-Threonine (⫾)-Threonine Thymine Thymol Toluene 1H-1,2,4-Triazol-3-amine 2,4,6-Triamino-1,3,5-triazine 2-Triazoethanol Tribenzylamine Tribromoacetaldehyde Tribromochloromethane Tribromofluoromethane Tribromomethane Tributoxyborane Tributylamine Tributyl phosphate Tributylphosphine oxide Trichloroacetaldehyde 2,2,2-Trichloroacetamide Trichloroacetic acid ionized Trichloroacetonitrile Trichloroacetyl chloride Trichlorobenzoquinone 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane Trichloromethane

Physical State g c lq g lq c c lq lq g lq g c c g c c c c lq g c c lq c lq g g lq g lq lq lq c lq c c aq g lq c lq g lq g lq g lq g lq g

⌬f H⬚ kJ · mol⫺1 300.0 ⫺71.7 ⫺216.9 ⫺175.1 44.2 ⫺554.8 ⫺249.0 ⫺468.4 80.2 115.0 64.1 111.6 25.1 ⫺89.1 22.9 ⫺807.2 ⫺758.8 ⫺462.8 ⫺309.7 12.4 50.4 76.8 ⫺72.4 94.6 140.6 ⫺130.3 12.6 ⫺190.0 ⫺28.5 23.8 ⫺1199.6 ⫺281.6 ⫺1456 ⫺460 ⫺234.5 ⫺358.2 ⫺503.3 ⫺517.6 ⫺280.8 ⫺269.9 ⫺177.4 ⫺144.6 ⫺191.5 ⫺151.2 ⫺43.6 ⫺9.0 ⫺301.3 ⫺268.3 ⫺134.5 ⫺102.7

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

Cp⬚ J · deg⫺1 · mol⫺1

255.3

54.7

313.2

80.9

121.2 126.8 134.0 147.6

181.2 278.9 222.8 336.9

123.8 72.9 173.2 104.9

21.8

115.9

275.8 ⫺154.0

cap height base of text

150.8 113.8 122.0

221.0 320.7

184.5

149.1

9.1 ⫺193.1 8.0 ⫺5.0

357.8 345.9 220.9 330.9

157.0 103.6

89.4 84.4 130.7 71.2

151.0

336.6

96.1

⫺77.5

227.4 323.1 232.6 337.1

19.9 ⫺236.8 ⫺249.3 73.7 ⫺76.0

324.8 255.4 309.7 201.7 295.7

144.3 93.3 150.9 89.0 124.4 80.3 121.6 78.0 114.2 65.7

⫺76.2

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.47

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 1,2,2-Trichloropropane 1,2,3-Trichloropropane 1,2,3-Trichloropropene 1,1,2-Trichlorotrifluoroethane 1,1,1-Tricyanoethane Tricyanoethylene Tridecane Tridecanoic acid 1-Tridecene Triethanolamine Triethoxyborane Triethoxymethane Triethylaluminum Triethylamine Triethylaminoborane Triethyl arsenite Triethylarsine Triethylbismuthine Triethylborane Triethylenediamine Triethylene glycol Triethyl phosphate Triethylphosphine Triethyl phosphite Triethylstibine Triethylsuccinic acid Triethyl thiophosphate Trifluoroacetic acid Trifluoroacetonitrile 1,1,1-Trifluoroethane 1,1,2-Trifluoroethane 2,2,2-Trifluoroethanol Trifluoroethylene Trifluoroiodoethane Trifluoroiodomethane Trifluoromethane (Trifluoromethyl)benzene 1,1,1-Trifluoro-2,4-pentanedione 3,3,3-Trifluoropropene Trihexylamine (⫾)-Trihydroxyglutaric acid 2,4,6-Trihydroxypryimidine Triiodomethane Triisopropyl phosphite Trimethoxyborane Trimethoxyethane Trimethoxymethane

Physical State

⌬f H⬚ kJ · mol⫺1

g lq g lq lq c c g c g c lq lq lq lq g lq lq lq lq lq g c lq lq lq lq lq c lq lq g g g lq g g g g g lq

⫺185.8 ⫺230.6 ⫺182.9 ⫺101.8 ⫺805.8 351.0 439.3 ⫺311.5 ⫺806.6 ⫺186.0 ⫺664.2 ⫺1047.4 ⫺687.3 ⫺236.8 ⫺127.7 ⫺92.8 ⫺198.6 ⫺706.7 13.0 169.9 ⫺194.6 ⫺157.7 ⫺14.2 ⫺804.2 ⫺1243 ⫺89.1 ⫺861.5 5.0 ⫺1066.5 ⫺972.8 ⫺1069.9 ⫺497.9 ⫺744.6 ⫺730.7 ⫺932.4 ⫺490.4 ⫺644.5 ⫺587.8 ⫺695.4 ⫺599.1 ⫺1040.2

g lq c c g lq g lq lq

⫺614.2 ⫺433.0 ⫺1490 ⫺634.7 251.0 ⫺980.3 ⫺899.1 ⫺612.0 ⫺570.0

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺97.8

382.9

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1 112.2 183.6

170.1

58.5

661.5

303.2

146.3

657.3

292.4 389.0

110.3

405.4

9.4 16.1 239.7

336.7 437.8 157.6

241.2

⫺461.9 ⫺678.3

298.1 279.9

77.9 78.2

⫺469.5

292.6

69.2

⫺572.0 ⫺658.9 ⫺511.3

307.5 259.6 372.6

70.9 51.1 130.4

178.0

356.2

75.1

219.9 160.9

short standard long

DEAN #37261

LEFT

(McGHP)

6.48

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Trimethylacetic acid Trimethylacetic anhydride 2⬘,4⬘,5⬘-Trimethylacetophenone 2⬘,4⬘,6⬘-Trimethylacetophenone Trimethylaluminum Trimethylamine std. state Trimethylamine-aluminum chloride adduct Trimethylamine-borane Trimethylammonium ion, std. state Trimethyl arsenite Trimethylarsine 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene 2,3,4-Trimethylbenzoic acid 2,3,5-Trimethylbenzoic acid 2,3,6-Trimethylbenzoic acid 2,4,5-Trimethylbenzoic acid 2,4,6-Trimethylbenzoic acid 3,4,5-Trimethylbenzoic acid 2,6,6-Trimethylbicyclo-[3.1.1]2-heptene Trimethylbismuthine Trimethylborane 2,2,3-Trimethylbutane 2,2,3-Trimethylbutane 2,3,3-Trimethyl-1-butene Trimethylchlorosilane cis,cis-1,3,5-Trimethylcyclohexane 1,1,2-Trimethylcyclopropane Trimethylene oxide (Oxetane) Trimethylgallium 2,3,5-Trimethylhexane Trimethylindium 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane 2,3,4-Trimethylpentane 2,2,4-Trimethyl-3-pentanone 2,4,4-Trimethyl-1-pentene

Physical State

⌬f H⬚ kJ · mol⫺1

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

lq lq lq lq

⫺564.4 ⫺779.9 ⫺252.3 ⫺267.4

lq lq g aq c

⫺136.4 ⫺45.7 ⫺23.7 ⫺76.0 ⫺879.1

⫺9.9 98.9 93.0

209.4 208.5 287.1 133.5

c

⫺142.5

70.7

187.0

aq lq g lq lq lq c c c c c c lq

⫺112.9 ⫺590.8 11.7 ⫺58.5 ⫺61.8 ⫺63.4 ⫺486.6 ⫺488.7 ⫺475.7 ⫺495.7 ⫺477.9 ⫺500.9 16.4

37.2

196.7

107.5 102.3 103.9

267.8 284.2 273.6

216.4 215.0 209.3

g g g lq lq lq g g

192.9 ⫺124.3 ⫺204.5 ⫺236.5 ⫺117.7 ⫺382.8 ⫺352.8 ⫺215.4

⫺35.9 4.3

314.7 383.3 292.2

88.5 164.6 213.5

⫺246.4 ⫺243.5 33.9

278.2 369.1 390.4

179.6

lq lq g g lq g lq g lq g lq g lq lq lq

⫺96.2 ⫺110.8 ⫺80.5 ⫺46.9 ⫺284.0 170.7 ⫺256.9 ⫺220.0 ⫺259.2 ⫺224.0 ⫺253.5 ⫺216.3 ⫺255.0 ⫺381.6 ⫺145.9

⫺9.8

273.9

9.3 17.1 6.9 13.7 10.6 18.9 10.7

327.6 425.2 328.0 423.2 334.4 431.5 329.3

86.4

306.3

155.6 137.9 91.8

188.9 239.1 245.6 247.3

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.49

THERMODYNAMIC PROPERTIES

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance 2,4,4-Trimethyl-2-pentene Trimethylphosphine Trimethylphosphine oxide Trimethyl phosphite Trimethylsilane Trimethylsilanol Trimethylstibine Trimethylsuccinic acid Trimethylsuccinic anhydride Trimethylthiacyclopropane Trimethyltin bromide Trimethyltin chloride Trimethylurea Trinitroacetonitrile 2,4,6-Trinitroanisole 1,3,5-Trinitrobenzene 1,1,1-Trinitroethane Trinitroglycerol Trinitromethane 2,4,6-Trinitrophenetole 2,4,6-Trinitrophenol 2,4,6-Trinitrophenylhydrazine 2,4,6-Trinitrotoluene 2,4,6-Trinitro-1,3-xylene Trioctylamine 1,3,6-Trioxacyclooctane 1,3,5-Trioxane Triphenylamine Triphenylarsine Triphenylbismuthine Triphenylborane Triphenylene 1,1,1-Triphenylethane 1,1,2-Triphenylethane Triphenylethylene 2,4,6-Triphenylimidazole Triphenylmethane Triphenylmethanol Triphenyl phosphate Triphenylphosphine Triphenylphosphine oxide Triphenylstibine Tripropoxyborane Tripropylamine Tripropynylamine Tris(acetylacetonato)chromium Tris(diethylamino)phosphine 1,1,1-Tris(hydroxymethyl)ethane

Physical State

⌬f H⬚ kJ · mol⫺1 ⫺142.4 ⫺122.2 ⫺477.8 ⫺741.0

lq lq c lq g lq g c c lq lq lq c lq c c lq lq lq g c c c c c lq lq c c c c c c c c c c c c c c c c lq lq lq c

⫺545.0 32.2 ⫺1000.8 ⫺688.3 ⫺60.5 ⫺185.4 ⫺213.0 ⫺330.5 183.7 ⫺157.3 ⫺37.2 ⫺96.9 ⫺370.9 ⫺32.8 ⫺0.2 ⫺204.6 ⫺214.3 36.8 ⫺65.5 ⫺102.5 ⫺584.9 ⫺515.9 ⫺522.5 234.7 310.0 469.0 48.5 151.8 157.2 130.2 233.5 272 171.2 ⫺3.4 ⫺757 232.2 ⫺60.3 329.3 ⫺1127.2 ⫺207.2 814.2 ⫺1533.0

lq c

⫺289.5 ⫺744.6

⌬f G⬚ kJ · mol⫺1 88.0

S⬚ J · deg⫺1 · mol⫺1

top of rh base of rh cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

311.7

331.0

117.9

133.0

114.4

504.2

329.2

254.7

514.6 412.5 272.8

312.1 329.3

295.0

short standard long

DEAN #37261

LEFT

(McGHP)

6.50

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.1 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (Continued)

Substance Tris(hydroxymethyl)nitromethane Tris(isopropoxy)borane Tris(trimethylsilyl)amine (⫺)-Tryptophane (⫺)-Tyrosine Undecane Undecanoic acid 1-Undecanol 1-Undecene 10-Undecenoic acid Uracil Urea Urea nitrate Urea oxalate 5-Ureidohydantoin Uric acid (⫾)-Valine Valylphenylalanine Vinyl acetate Vinylbenzene Vinylcyclohexane 4-Vinylcyclohexene Vinylcyclopentane Vinylcyclopropane 2-Vinylpyridine Xanthine Xanthone 1,2-Xylene 1,3-Xylene 1,4-Xylene Xylitol D-(⫹)-Xylose

Physical State

⌬f H⬚ kJ · mol⫺1

c

⫺735.6

lq c c c lq c lq g c c c g c c c c c c g lq lq lq lq lq lq c c lq g lq g lq g c c

⫺293.3 ⫺725.1 ⫺415.3 ⫺685.1 ⫺327.2 ⫺735.9 ⫺504.8 ⫺144.8 ⫺577 ⫺429.4 ⫺333.1 ⫺245.8 ⫺564.0 ⫺1528.4 ⫺718.0 ⫺618.8 ⫺628.9 ⫺767.8 ⫺314.4 103.8 ⫺88.7 26.8 ⫺34.8 122.5 157.1 ⫺379.6 ⫺191.5 ⫺24.4 19.1 ⫺25.4 17.3 ⫺24.4 18.0 ⫺1118.5 ⫺1057.8

⌬f G⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺119.4 ⫺385.7 22.8

251.0 214.0 458.1

238.2 216.4 344.9

129.5

579.4

246.7

⫺196.8

104.6

120.5 93.1

⫺434.0 ⫺358.8 ⫺359.0

195.1 173.2 178.9

166.1 168.8

⫺165.9

161.1

151.3

110.3 122.1 107.7 118.9 110.1 121.1

246.5 352.8 252.2 357.7 247.4 352.4

186.1 133.3 183.3 127.6 181.5 126.9

cap height base of text

Cp⬚ J · deg⫺1 · mol⫺1

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.51

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds

top of rh base of rh cap height base of text

Abbreviations Used in the Table ⌬Hm, enthalpy of melting (at the melting point) in kJ · mol⫺1 ⌬Hv, enthalpy of vaporization (at the boiling point) in kJ · mol⫺1 ⌬Hs, enthalpy of sublimation (or vaporization at 298 K) in kJ · mol⫺1 Cp, specific heat (at temperature specified on the Kelvin scale) for the physical state in existence (or specified: c, lq, g) at that temperature in J · K⫺1 · mol⫺1 ⌬Ht, enthalpy of transition (at temperature specified, superscript, measured in degrees Celsius) in kJ · mol⫺1 Cp Substance Acenaphthene Acenaphthylene Acetaldehyde Acetamide Acetanilide Acetic acid Acetic anhydride Acetone Acetonitrile, ⌬Ht ⫽ 0.22⫺56 Acetophenone Acetyl bromide Acetyl chloride Acetylene Acetylene-d2 Acetylenedicarbonitrile Acetyl fluoride Acetyl iodide Acrylic acid Acrylonitrile Adamantane Adenine ␣-Alanine Allyl tert-butyl sulfide Allyl ethyl sulfone Allyl ethyl sulfoxide Allyl methyl sulfone Allyl trichloroacetate 3-Aminoacetophenone 4-Aminoacetophenone 2-Aminobenzoic acid 3-Aminobenzoic acid 4-Aminobenzoic acid 2-Aminoethanol Aniline Anthracene 9,10-Anthraquinone cis-Azobenzene trans-Azobenzene Azobutane Azomethane Azomethane-d6

⌬Hm

⌬Hv

⌬Hs

21.54

54.73

3.24 15.71

25.8 56.1 64.7 23.7 38.2 29.1 29.8 38.8

86.2 73.0 25.5 78.7 80.8 23.4 48.3 31.0 32.9 55.9 33.1 30.1 21.3

11.54 10.5 5.69 8.17

3.8

11.16 6.23

12.1 15.9 20.5 21.8 20.9 20.5 10.56 28.83 22.04 22.6

17.0

44.1 32.6

28.8 25.1 38.5 54.3 33.5 59.7 108.8 138.1 44.4 83.7 71.6 79.5 52.3

400 K

600 K

800 K

1000 K

66.3(g)

85.9

101.3

112.5

79.7 129.1 92.1 61.2

106.2 174.1 122.8 76.8

125.5 204.6 144.9 89.0

139.3 226.4 162.0 98.3

78.9 50.1 54.8 94.8

97.0 58.1 61.9 106.2

110.0 63.5 67.4 114.1

119.7 68.0 71.8 119.8

96.0 76.8

123.4 96.7

142.0 110.6

155.3 120.8

143.0

192.8

225.1

230.9

93.9 110.7

123.1 142.8

145.7 165.2

162.6 180.6

104.9 128.0 116.1 50.9 42.4 56.5 88.5

55.8 101.5 112.1 92.9

93.8 49.3

short standard long

DEAN #37261

LEFT

(McGHP)

6.52

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance Azoisopropane Azopropane trans-Azoxybenzene Azulene Benzaldehyde Benzamide 1,2-Benzanthracene 2,3-Benzanthracene 1,2-Benzanthracene-9,10-dione Benzene Benzeneacetic acid 1,3-Benzenedicarboxylic acid 1,4-Benzenedicarboxylic acid Benzenethiol Benzil Benzoic acid Benzoic anhydride Benzonitrile Benzo[def]phenanthrene Benzophenone 1,4-Benzoquinone Benzo[f]quinoline Benzo[h]quinoline Benzo[b]thiophene, ⌬Ht ⫽ 3.0⫺11.6 Benzotrifluoride Benzoyl bromide Benzoyl chloride Benzoyl iodide 4-Benzphenanthrene Benzyl acetate Benzyl alcohol Benzylamine Benzyl benzoate Benzyl bromide Benzyl chloride Benzyl ethyl sulfide Benzyl iodide Benzyl mercaptan Benzyl methyl ketone Benzyl methyl sulfide Bicyclo[1.1.0]butane Bicyclo[2.2.1]hepta-2,5-dione Bicyclo[2.2.1]heptane Bicyclo[4.1.0]heptane Bicyclo[2.2.1]-2-heptene Bicyclo[3.1.0]hexane Bicyclohexyl Bicyclo[2.2.2]octane Bicyclo[4.2.0]octane Bicyclo[5.1.0]octane

⌬Hm

⌬Hv

⌬Hs

400 K

600 K

800 K

1000 K

176.4

248.2

295.4

327.4

113.5(g)

160.1

190.5

211.4

138.4

196.7

234.9

260.7

140.8

187.4

217.9

238.8

36.0 39.9 17.93 12.1 9.32 18.49

9.95 14.49

11.48 23.54 18.06 17.2 10.88 17.1 18.19 18.53

55.5 42.5

76.8 49.8

30.7

123.0 126 82.8 33.8

39.9

106.7 98.3 47.6

50.6 45.9

91.1 96.4 52.5 100.2 94.1 62.8 83.1 80.8

11.8 37.6 58.6 54.8 61.9 106.3 8.97

49.4 50.5 53.6

60.3 60.2 77.8 47.3 51.5 56.9 47.3 56.6 49.0 53.6 23.4

32.9 40.2 38.0 38.8 32.8 58.0 48.0 42.0 43.5

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.53

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance Bicyclo[2.2.2]-2-octene Bicyclopropyl Biphenyl Biphenylene Bis(2-butoxyethyl) ether Bis(2-chloroethyl) ether Bis(2-ethoxyethyl) ether Bis(2-ethoxymethyl) ether Bis(2-hydroxyethyl) ether Bis(2-methoxyethyl) ether Bromobenzene 4-Bromobenzoic acid 1-Bromobutane (⫾)-2-Bromobutane 1-Bromo-2-chloroethane Bromochloromethane 1-Bromo-3-chloropropane 1-Bromo-2-chloro-1,1,2-trifluoroethane Bromochloro-2,2,2-trifluoroethane 1-Bromododecane Bromoethane Bromoethylene 1-Bromoheptane 1-Bromohexadecane 1-Bromohexane Bromomethane, ⌬Ht ⫽ 0.47⫺99.4 1-Bromo-2-methylpropane 2-Bromo-2-methylpropane ⌬Ht ⫽ 5.7⫺64.5 ⌬Ht ⫽ 1.0⫺41.6 1-Bromonaphthalene 1-Bromooctane 1-Bromopentane 1-Bromopropane 2-Bromopropane 3-Bromopropene Bromotrichloromethane Bromotrifluoromethane Bromotrimethylsilane 1,2-Butadiene 1,3-Butadiene 1,3-Butadiyne Butanal Butanamide Butane, ⌬Ht ⫽ 2.1⫺165.6 1,2-Butanediamine Butanedinitrile 1,3-Butanediol 1,4-Butanediol 2,3-Butanediol

⌬Hm

18.6

8.66

10.62 6.69 6.89

5.86 5.12

5.98

⌬Hv

45.6 55.9 45.2 49.0 36.2 52.3 43.1 37.9 32.5 30.8 33.7 30.0 37.6 28.3 28.1 74.8 27.0 23.4

⌬Hs 43.8 33.5 81.8 84.3

400 K

600 K

800 K

1000 K

221.0

307.7

363.7

401.7

127.4

171.5

199.9

219.2

136.6 138.1

180.0 214.7

211.2 238.2

234.4

79.2 66.6

102.8 83.0

119.6 94.1 74.8

132.2 102.3

50.0

62.7

72.2

79.5

146.1

190.7

220.3

241.6

165.6 107.5 110.2

219.0 140.8 144.0

257.5 164.9 167.7

286.0 182.8 185.2

79.3

91.3

97.5

100.9

98.4 101.2 84.4 126.4

128.5 154.1 96.8 165.7

150.7 169.5 105.1 195.0

167.4

123.9

168.6

201.8

226.9

44.7 57.3 44.5 87.9 36.7 34.4 38.2 32.8 44.1 30.1 29.8 28.0 18.2 50.6 94.4 45.9 22.8 34.8 31.8

1.97

23.9 31.3 29.2

15.16

39.3

11.46 6.53

35.0 29.8 28.3 30.2

52.5 55.8 41.3 32.0 30.2 32.7

7.0 7.98

24.0 22.5

32.6 23.2 20.9

11.09 17.6 4.66

31.5

3.7

48.5 58.5

2.54

22.4

34.5 85.9 21.0 46.3 70.0 67.8 76.6 59.2

111.3 216.3

short standard long

DEAN #37261

LEFT

(McGHP)

6.54

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance 2,3-Butanedione 1,4-Butanedithiol Butanenitrile meso-1,2,3,4-Butanetetrol 1,4-Butanedithiol 1-Butanethiol 2-Butanethiol 1,2,4-Butanetriol Butanoic acid Butanoic anhydride 1-Butanol 2-Butanol 2-Butanone trans-2-Butenal 1-Butene cis-2-Butene trans-2-Butene cis-2-Butenedinitrile cis-2-Butenedioic acid trans-2-Butenedioic acid cis-2-Butene-1,4-diol trans-2-Butene-1,4-diol cis-2-Butenenitrile trans-2-Butenenitrile 3-Butenenitrile cis-2-Butenoic acid trans-2-Butenoic acid cis-2-Buten-1-ol 1-Buten-3-yne 2-Butoxyethanol 1-tert-Butoxy-2-ethoxyethane 2-(2-Butoxyethoxy)ethanol 2-Butoxyethyl acetate 1-tert-Butoxy-2-methoxyethane N-Butylacetamide Butyl acetate tert-Butyl acetate Butylamine sec-Butylamine tert-Butylamine Butylbenzene sec-Butylbenzene tert-Butylbenzene sec-Butyl butanoate Butyl chloroacetate Butyl 2-chlorobutanoate Butyl 3-chlorobutanoate Butyl 4-chlorobutanoate Butyl 2-chloropropanoate Butyl 3-chlorobutanoate

⌬Hm

⌬Hv

5.02

33.7

10.46 6.5

8.44

32.2 30.6 58.6 41.8 50.0 43.3 40.8 31.3

3.9 7.58 9.8

22.1 23.3 22.7

11.08 9.28

⌬Hs 38.7 55.1 39.3 135.1 49.7 36.6 34.0

400 K

600 K

800 K

1000 K

118.8

155.1

181.9

201.8

146.2 148.0

194.7 194.2

233.0 227.2

263.4 251.1

137.2 141.0 124.7

183.7 187.1 163.6

218.0 220.4 192.8

243.8 245.3 214.8

109.0 101.8 108.9

147.1 141.4 145.6

174.9 171.0 184.9

195.9 193.1 194.9

89.0

111.6

127.2

138.7

148.3 148.1 152.6 229.1

197.9 199.0 204.5 314.6

234.4 236.1 240.5 373.9

261.7 261.7 266.9 416.3

40.5 52.3 49.7 34.8 34.5 20.2 22.2 21.4 72.0 110.0 136.3

66.1 69.0 38.9 40.0 40.0 12.57 12.98 46.4 56.6 50.9 28.0 38.5

0.88 11.22 9.83 8.39

36.3 33.1 31.8 29.9 28.3 38.9 38.0 37.6

59.5 47.8 76.1 43.9 38.0 35.7 32.8 29.6 51.4 48.0 47.7 47.3 51.0 52.7 53.1 54.4 54.4 55.4

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.55

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance Butyl crotonate sec-Butyl crotonate Butylcyclohexane Butylcyclopentane N-Butyldiacetimide Butyl dichloroacetate Butylethylamine Butyl ethyl ether Butyl ethyl sulfide tert-Butyl ethyl sulfide Butyl formate tert-Butyl hydroperoxide Butylisopropylamine Butyllithium Butyl methyl ether sec-Butyl methyl ether tert-Butyl methyl ether Butyl methyl sulfide tert-Butyl methyl sulfide Butyl methyl sulfone tert-Butyl methyl sulfone Butyl octadecanoate tert-Butyl peroxide Butyl propyl ether Butyl thiolacetate Butyl trichloroacetate Butyl vinyl ether 1-Butyne 2-Butyne 2-Butynedinitrile 4-Butyrolactone Butyrophenone (⫹)-Camphor 9H-Carbazole Chloroacetic acid Chloroacetyl chloride 2-Chloroaniline 2-Chlorobenzaldehyde Chlorobenzene 2-Chlorobenzoic acid 3-Chlorobenzoic acid 4-Chlorobenzoic acid Chloro-1,4-benzoquinone 1-Chlorobutane 2-Chlorobutane Chlorocyclohexane 1-Chloro-1,1-difluoroethane Chlorodifluoromethane 2-Chloro-1,4-dihydroxybenzene Chlorodimethylsilane

⌬Hm

14.16 11.3

12.4 7.1

⌬Hv

38.5 36.2

34.0 31.6 37.0 33.5 36.6 34.5

12.5 8.4

29.6 28.1 27.9 34.5 31.5

⌬Hs 51.9 49.4 49.4 45.9 64.4 52.3 40.2 36.3 44.5 39.3 41.1 47.7 42.1 107.1 32.4 30.2 29.8 40.5 35.8 76.2 82.4

400 K

600 K

800 K

1000 K

276.1 241.7

289.5 336.3

469.9 407.3

525.9 480.3

202.4

271.8

325.3

367.2

174.6

233.0

278.4

314.1

99.9 94.6

129.0 124.2

150.4 147.0

166.7 164.4

128.1

172.2

200.4

219.6

135.1 136.1

179.0 180.7

210.5 212.7

234.0 236.8

65.4

78.9

87.2

92.4

56.90 33.7

6.0 9.23

31.6 24.5 26.5

9.57

52.2

6.84 26.9 12.28

59.5

11.88

44.4

9.61 25.73

35.2

31.8 40.2 48.1 53.6 36.2 23.3 26.6 28.8 60.7

30.4 29.2 2.69 4.12

84.5 75.3 38.9 56.8 53.1 41.0 79.5 82.0 87.9 69.0 33.5 31.5 43.5

22.4 20.2 69.0 26.2

short standard long

DEAN #37261

LEFT

(McGHP)

6.56

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance Chlorodiphenylsilane 1-Chloro-2,3-epoxypropane Chloroethane 2-Chloroethanol 1-Chloro-2-ethylbenzene 1-Chloro-4-ethylbenzene Chloroethylene 2-Chloroethyl vinyl ether Chloroethyne 1-Chloroheptane 1-Chlorohexane Chlorohydroquinone Chloromethane 1-Chloro-2-methylbenzene 1-Chloro-3-methylbenzene 1-Chloro-4-methylbenzene 1-Chloro-3-methylbutane 1-Chloro-2-methylpropane 2-Chloro-2-methylpropane ⌬Ht ⫽ 1.7⫺90.1 ⌬Ht ⫽ 5.8⫺53.6 1-Chloronaphthalene 2-Chloronaphthalene 1-Chloro-3-nitrobenzene 1-Chloro-4-nitrobenzene 1-Chlorooctane Chloropentafluoroacetone Chloropentafluorobenzene Chloropentafluoroethane 1-Chloropentane 2-Chloropentane 2-Chlorophenol 3-Chlorophenol 4-Chlorophenol 1-Chloropropane 2-Chloropropane 3-Chloro-1-propene Chlorotrifluoroethylene Chlorotrifluoromethane Chlorotrimethylsilane Chlorotrinitromethane Chrysene Coronene 1,2-Cresol 1,3-Cresol 1,4-Cresol Cubane Cyanamide Cyanogen Cyclobutane, ⌬Ht ⫽ 5.8⫺126.8

⌬Hm

⌬Hv

4.45

33.1 24.7 41.4

⌬Hs

400 K

600 K

800 K

1000 K

77.6

101.6

118.8

131.7

65.0

82.1

93.5

101.9

69.5 40.6

47.3 48.1 4.75

20.8 38.2

35.7 6.43 8.37 10.46

21.4 37.5

2.09

38.7 32.0 29.2 27.6

12.90

52.1

60.2

66.8

71.0

74.3

47.7 42.8 69.0 18.9

48.2

61.3

71.3

78.9

36.2 31.7 29.0

136.1 142.3

180.7 184.9

212.7 215.5

236.8 238.5

164.2

218.0

256.8

285.6

106.1 108.7 92.6

139.9 143.1 111.0

164.2 167.1 137.8

182.4 184.8 151.9

77.5

90.3

96.9

100.5

76.0 61.7 73.9 80.3

166.3 162.1 161.7

220.8 218.7 218.0

257.5 256.4 255.7

287.9 286.6 286.5

19.7 23.5

61.9(g) 100.0

68.2 145.4

72.9 177.5

76.4 200.7

65.3 82.0

19.37 20.77

1.88

12.52 14.91 14.07 5.54 7.39 5.6

34.8 19.4 33.2 31.8

27.2 26.3 29.0 20.8 15.8 27.6

26.15 19.2 13.94 9.41 11.89

45.2 47.4 47.5

8.76 8.1 1.1

68.6 23.3 24.2

52.4 25.3 41.1 38.2 36.0 53.1 51.9 28.4 26.9 28.2

30.1 45.4 124.5

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.57

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance Cyclobutanecarbonitrile Cyclobutanenitrile Cyclobutene Cyclobutylamine Cyclododecane Cycloheptane ⌬Ht ⫽ 5.0⫺138.4 ⌬Ht ⫽ 0.3⫺75.0 ⌬Ht ⫽ 0.5⫺60.8 Cycloheptanone 1,3,5-Cycloheptatriene ⌬Ht ⫽ 2.4⫺119.2 Cyclohexane ⌬Ht ⫽ 6.7⫺87 Cyclohexanecarbonitrile Cyclohexanethiol Cyclohexanol ⌬Ht ⫽ 8.2⫺9.7 Cyclohexanone Cyclohexene ⌬Ht ⫽ 4.3⫺134.4 1-Cyclohexenecarbonitrile Cyclohexylamine Cyclohexylbenzene Cyclohexylcyclohexane cis, cis-1,5-Cyclooctadiene Cyclooctane ⌬Ht ⫽ 6.3⫺106.7 ⌬Ht ⫽ 0.5⫺89.4 Cyclooctanone 1,3,5,7-Cyclooctatetraene Cyclooctene Cyclopentadiene Cyclopentane ⌬Ht ⫽ 4.8⫺150.8 ⌬Ht ⫽ 0.3⫺135.1 Cyclopentanecarbonitrile 1-Cyclopentenecarbonitrile Cyclopentanethiol Cyclopentanol Cyclopentanone Cyclopentene ⌬Ht ⫽ 0.5⫺186.1 Cyclopentylamine Cyclopropane Cyclopropanecarbonitrile Cyclopropylamine Cyclopropylbenzene Cyclopropyl methyl ketone Decafluorobutane

⌬Hm

⌬Hv

⌬Hs

36.9

44.3 40.0 35.6 76.4 38.5

400 K

600 K

800 K

1000 K

90.3

126.8

151.7

169.6

175.0

261.2

322.3

365.7

155.4

209.5

245.1

270.2

1.88

33.2

1.2

38.7

2.63

30.0

33.0

149.9

225.2

279.3

317.2

1.76

37.1 45.5

51.9 44.6 62.0

172.1

248.1

302.0

339.5

3.29

40.3 30.5

45.1 33.5

150.6 144.9

221.3 206.9

272.0 248.9

305.4 278.7

53.5 43.7 59.9 58.0 43.4 43.3

200.1

297.1

365.3

414.3

160.9

220.8

260.4

288.2

118.7

178.1

220.1

250.4

144.5

203.6

245.2

275.5

104.9

155.6

191.5

217.3

76.6

109.4

140.5

148.1

51.9

36.1 15.30 51.9 2.41

11.3

0.61

7.8

35.9

36.4

27.3

35.3 36.4

3.36 8.31 5.44

20.1 35.6

13.18 34.1 22.9

54.4 43.1 47.0 28.4 28.5

43.4 45.0 41.4 57.6 42.7 28.1 40.2 16.9 41.9 31.3 50.2 38.4

short standard long

DEAN #37261

LEFT

(McGHP)

6.58

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance

⌬Hm

⌬Hv

⌬Hs

cis-Decahydronaphthalene ⌬Ht ⫽ 2.1⫺57.1 trans-Decahydronaphthalene Decanal Decane Decanedioic acid Decanenitrile 1-Decanethiol Decanoic acid 1-Decanol 1-Decene ⌬Ht ⫽ 8.0⫺74.8 1-Decyne Deoxybenzoin Dibenz[de,kl]anthracene Dibenzoyl peroxide Dibenzyl ether Dibenzyl sulfide Dibenzyl sulfone 1,2-Dibromobutane 1,4-Dibromobutane 2,3-Dibromobutane 1,2-Dibromo-1-chloro-1,1,2-trifluoroethane 1,2-Dibromocycloheptane 1,2-Dibromocyclohexane 1,2-Dibromocyclooctane 1,2-Dibromoethane 1,2-Dibromoheptane Dibromomethane 1,2-Dibromopropane 1,3-Dibromopropane 1,2-Dibromotetrafluoroethane 1,2-Dibutoxyethane Dibutoxymethane Dibutylamine N,N-Dibutyl-1-butanamine Dibutyl decanedioate Dibutyl disulfide Di-tert-butyl disulfide Dibutyl ether Di-sec-butyl ether Di-tert-butyl ether Dibutylmercury Di-tert-butyl peroxide Dibutyl 1,2-phthalate Dibutyl sulfate Dibutyl sulfide Di-tert-butyl sulfide Dibutyl sulfite Dibutyl sulfone

9.49

41.0

50.2

14.41

40.2

43.5

28.78 40.8

38.8

31.0 28.02 37.7 21.10

46.4

51.4 160.7 66.8 65.5 118.8 81.5 50.4

49.8 38.7

400 K

600 K

800 K

1000 K

237.0

352.0

432.5

489.5

237.6 300.4 298.1

352.3 400.4 403.2

432.6 472.8 480.8

489.2 525.9 536.4

320.6

429.4

510.9

573.1

187.2 283.6

418.2 381.9

495.9 453.0

553.3 505.9

274.6

363.8

428.5

476.6

153.9

195.4

224.3

244.8

99.7

122.3

137.8

149.8

63.0 124.4

74.8 157.4

82.5 179.5

88.0 195.6

286.1

376.5

442.8

493.1

254.3

340.1

403.8

451.3

259.8

348.6

420.8

475.8

93.3 125.5 102.5

31.4 20.2

31.2

10.84

8.94 13.6 7.04

34.8 32.9 35.6 27.0 47.8 38.4 46.9 92.9 46.9 36.5 34.1 32.2

79.2 19.4

41.3 33.3

93.3 125.5 50.3 53.1 37.7 35.0 52.0 50.5 54.6 41.7 54.4 37.0 41.7 47.5 28.4 58.8 48.1 49.5

64.5 54.3 45.0 40.8 37.6 63.5 31.8 91.6 75.9 53.0 43.8 67.8 100.4

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.59

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance Dichloroacetyl chloride 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene 2,6-Dichlorobenzoquinone 2,2⬘-Dichlorobiphenyl 4,4⬘-Dichlorobiphenyl 1,2-Dichlorobutane 1,4-Dichlorobutane Dichlorodifluoromethane Dichlorodimethylsilane Dichlorodiphenylsilane 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene 2,2-Dichloroethyl ether Dichlorofluoromethane 1,2-Dichlorohexafluoropropane 1,2-Dichlorohexane Dichloromethane 1,2-Dichloro-4-methylbenzene 1,2-Dichloropentane 1,5-Dichloropentane (⫾)-1,2-Dichloropropane 1,3-Dichloropropane 2,2-Dichloropropane 1,3-Dichloro-2-propanol 1,2-Dichlorotetrafluoroethane Dicyanoacetylene Dicyclopentadienyliron Dicyclopropyl ketone Diethanolamine 1,1-Diethoxyethane 1,2-Diethoxyethane Diethoxymethane 1,3-Diethoxypropane 2,2-Diethoxypropane Diethylamine 1,2-Diethylbenzene 1,3-Diethylbenzene 1,4-Diethylbenzene Diethyl carbonate Diethyl disulfide Diethylene glycol diethyl ether Diethylene glycol dimethyl ether Diethylene glycol monoethyl ether Diethylene glycol monomethyl ether Diethyl ether

⌬Hm

⌬Hv

12.93 12.64 17.15

39.7 38.6 38.8

33.9 4.14

8.84 8.83 6.51 7.20 11.98

6.00 10.68

⌬Hs 39.3 50.2 48.6 49.0 69.9 96.2 103.8 39.6 46.4

20.1

28.9 32.0 26.1 30.2 28.9 38.4 25.2 26.3 28.1 36.5

6.40

31.8 35.2 29.3

6.32

23.3

34.3 69.5 30.6 35.2 26.5 31.0 29.3

26.9 48.2 28.8 43.9 50.7 36.0 40.8 32.6 66.9

400 K

600 K

800 K

1000 K

142.8 143.0 143.3

184.4 184.5 184.8

210.4 210.4 210.7

227.7 227.7 227.9

82.4

93.6

99.1

100.0

91.4 92.1 78.7 77.0 77.7

113.7 112.6 93.9 93.0 93.2

128.8 127.2 103.4 102.9 102.9

139.8 138.1 110.0 109.8 109.8

70.2

82.4

89.6

94.2

59.6

72.4

80.8

86.8

119.7 120.0 127.9

152.6 151.5 159.2

175.6 173.9 179.9

192.8 190.4 194.8

143.9 234.4 230.2 228.8

197.2 316.6 314.6 313.1

235.0 374.6 379.7 372.5

263.2 416.3 415.8 414.9

171.1

218.6

251.8

276.0

138.1

183.8

218.7

244.8

28.8 73.6 53.7 25.10

16.8 11.0 10.6 9.4 13.60

7.27

65.2 36.3 36.3 31.3 37.2 29.1 39.4 39.4 39.4 36.2 37.6 49.0 36.2 47.5 46.6 26.5

43.2 43.2 35.7 45.9 31.8 31.3 52.8 52.5 52.5 43.6 45.2 58.4 44.7

27.1

short standard long

DEAN #37261

LEFT

(McGHP)

6.60

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance Diethyl malonate Diethyl oxalate Diethyl peroxide 3,3-Diethylpentane Diethyl 1,2-phthalate Diethyl sulfide Diethyl sulfite Diethyl sulfone Diethyl sulfoxide Diethylzinc 1,2-Difluorobenzene 1,3-Difluorobenzene 1,4-Difluorobenzene 2,2⬘-Difluorobiphenyl 4,4⬘-Difluorobiphenyl 1,1-Difluoroethane 1,1-Difluoroethylene Difluoromethane 9,10-Dihydroanthracene Dihydro-2H-pyran 5,12-Dihydrotetracene 2,3-Dihydrothiophene 2,5-Dihydrothiophene 2,4-Dihydrothiophene-1,1-dioxide 1,4-Dihydroxybenzene 1,2-Diiodobenzene 1,2-Diiodoethane Diiodomethane Diisobutylamine Diisobutyl ether Diisobutyl sulfide Diisopropylamine Diisopropyl ether Diisopropylmercury Diisopropyl sulfide Diketene 1,2-Dimethoxybenzene 1,1-Dimethoxyethane 1,2-Dimethoxyethane Dimethoxymethane 2,2-Dimethoxypropane N,N-Dimethylacetamide Dimethylamine Dimethylaminomethanol N,N-Dimethylaminotrimethylsilane N,N-Dimethylaniline 1,4-Dimethylbicyclo[2.2.1]heptane 2,3-Dimethylbicyclo[2.2.1]-2-heptene 2,2-Dimethylbutane

⌬Hm

⌬Hv 54.8 42.0

10.09

34.6

11.90

31.8

11.1 8.58

32.2 31.1 31.8

21.6

33.2 34.8 27.11

44.80

42.5 34.0

11.03 10.4 16.04

30.4 29.1 33.8 36.8 48.2

12.60 8.33

32.4

10.42 5.94

43.4 26.4

0.58

33.3 34.9 26.3

⌬Hs 63.5 30.5 42.0 88.3 35.8 48.5 86.2 62.3 40.2 36.2 34.6 35.5 95.0 91.2 19.1

93.3 32.2 115.9 37.7 40.0 62.8 99.2 64.9 65.7 51.0 39.3 40.9 48.7 34.6 32.1 53.6 39.6 42.9 66.9 30.5 36.4 35.1 29.4 50.2 25.0 50.2 31.8 52.8 38.9 42.2 27.7

400 K

600 K

800 K

1000 K

145.0

192.9

229.7

258.5

137.1 137.0 137.4

181.3 180.5 180.1

209.7 207.8 207.8

229.0 225.6 225.7

83.4 71.8 51.1

107.5 89.2 65.8

124.3 100.2 76.2

136.3 107.7 83.7

96.0 65.9

116.8 76.9

131.3 83.9

141.6 89.1

196.2

262.0

311.3

348.0

211.9

277.1

322.7

356.6

87.4

118.9

142.0

159.8

182.8

251.0

298.7

333.5

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.61

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance ⌬Ht ⫽ 5.4 ⌬Ht ⫽ 0.3⫺132.3 2,3-Dimethylbutane ⌬Ht ⫽ 6.5⫺137.1 2,2-Dimethyl-1-butanol 2,3-Dimethyl-1-butanol 3,3-Dimethyl-1-butanol 2,3-Dimethyl-2-butanol (⫾)-3,3-Dimethyl-2-butanol 3,3-Dimethyl-2-butanone 2,3-Dimethyl-1-butene 3.3-Dimethyl-1-butene ⌬Ht ⫽ 4.3⫺148.3 2,3-Dimethyl-2-butene ⌬Ht ⫽ 3.5⫺76.3 Di(3-methylbutyl) ether Dimethylcadmium 1,1-Dimethylcyclohexane ⌬Ht ⫽ 6.0⫺120.0 cis-1,2-Dimethylcyclohexane ⌬Ht ⫽ 8.3⫺100.6 trans-1,2-Dimethylcyclohexane cis-1,3-Dimethylcyclohexane trans-1,3-Dimethylcyclohexane cis-1,4-Dimethylcyclohexane trans-1,4-Dimethylcyclohexane 1,1-Dimethylcyclopentane ⌬Ht ⫽ 6.5⫺126.4 cis-1,2-Dimethylcyclopentane ⌬Ht ⫽ 6.7⫺131.7 trans-1,2-Dimethylcyclopentane cis-1,3-Dimethylcyclopentane trans-1,3-Dimethylcyclopentane cis-2,4-Dimethyl-1,3-dioxane 4,5-Dimethyl-1,3-dioxane 5,5-Dimethyl-1,3-dioxane Dimethyl disulfide Dimethyl ether N,N-Dimethylformamide Dimethylglyoxime 2,2-Dimethylheptane 2,6-Dimethyl-4-heptanone 2,2-Dimethylhexane 2,3-Dimethylhexane 2,4-Dimethylhexane 2,5-Dimethylhexane 3,3-Dimethylhexane 3,4-Dimethylhexane cis-2,2-Dimethyl-3-hexene

⌬Hm

⌬Hv

⌬Hs

0.80

27.4

29.1 56.1

1.1

42.6 47.3 46.4 40.4 43.9 33.4 27.4 25.7

5.46

29.6

400 K

600 K

800 K

1000 K

181.2

247.7

314.6

331.0

37.9 29.2 27.1

178.2 162.8

231.8 223.4

272.0 266.1

302.1 297.1

32.5

156.8

216.7

262.7

297.7

⫺147.3

51.0

35.2 2.06

32.5

38.0 37.9

212.1

310.0

379.5

427.6

1.64

33.5

39.7

213.8

309.6

377.0

424.3

10.49 10.82 9.86 9.31 12.33 1.1

33.0 32.9 33.4 33.3 32.6 30.3

38.4 38.3 39.2 39.0 37.9 33.8

217.2 214.2 213.8 213.8 215.9 182.2

312.1 310.5 308.8 308.8 312.1 262.6

378.7 378.7 375.7 375.7 378.9 318.7

425.5 426.8 423.0 423.0 425.7 359.1

1.7

31.7

35.7

182.7

262.4

317.9

358.0

7.2 7.4 7.3

30.9 30.4 30.8

182.9 182.9 182.9

262.2 262.2 262.2

317.3 317.3 317.3

357.4 357.4 357.4

9.19 4.94 16.15

33.8 21.5 38.4

34.6 34.2 34.5 39.9 42.5 41.3 37.9 18.5 46.9 97.1

110.3 79.6

137.4 105.3

157.6 125.7

172.8 141.4

8.90 6.78

12.95 6.98

39.9 32.1 33.2 32.5 32.5 32.3 33.2

50.9 37.3 38.8 37.8 37.9 37.5 39.0 37.2

short standard long

DEAN #37261

LEFT

(McGHP)

6.62

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance trans-2,2-Dimethyl-3-hexene 1,1-Dimethylhydrazine 1,2-Dimethylhydrazine 3,5-Dimethylisoxazole Dimethyl maleate Dimethylmercury 6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane 2,4-Dimethyloctane Dimethyl oxalate 3,3-Dimethyloxetane 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane 2,2-Dimethyl-3-pentanone 2,4-Dimethyl-3-pentanone 2,4-Dimethyl-1-pentene 4,4-Dimethyl-1-pentene 2,4-Dimethyl-2-pentene cis-4,4-Dimethyl-2-pentene trans-4,4-Dimethyl-2-pentene 2,7-Dimethylphenanthrene 4,5-Dimethylphenanthrene 9,10-Dimethylphenanthrene 2,3-Dimethylphenol 2,4-Dimethylphenol 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol 3,5-Dimethylphenol Dimethyl 1,2-phthalate 2,2-Dimethylpropane ⌬Ht ⫽ 2.6⫺133.1 2,2-Dimethylpropanenitrile 2,2-Dimethyl-1-propanol 2,3-Dimethylpyridine 2,4-Dimethylpyridine 2,5-Dimethylpyridine 2,6-Dimethylpyridine 3,4-Dimethylpyridine 3,5-Dimethylpyridine Dimethyl sulfate Dimethyl sulfide Dimethyl sulfite Dimethyl sulfone Dimethyl sulfoxide 2,2-Dimethylthiacyclopropane Dimethylzinc Dinitromethane

⌬Hm

⌬Hv

10.1

32.6 35.2

14.7 40.2 36.5

6.69 7.07 11.18

47.1 46.9 44.5 49.7 49.3 22.7

21.8

32.4 9.6 39.1 38.5

37.3

30.9 29.2 30.5 29.6 29.6 36.1 34.6

21.02 23.38 18.90 18.13 18.00 162.7 3.10

10.04

37.5 40.0 39.5

7.99

27.0

14.37

43.1

400 K

600 K

800 K

1000 K

211.0 211.0 211.0 211.0

285.9 285.9 285.9 285.9

340.7 340.7 340.7 340.7

381.6 381.6 381.6 381.6

157.1

218.5

254.3

283.7

88.4

113.0

132.2

147.2

37.3 35.0 39.3 45.2 44.3 34.6 46.4 47.1 47.4 33.9 32.4 34.3 32.9 33.0 42.3 41.5 33.2 29.0 34.4 32.7 32.7 106.7 104.6 119.5 84.0 65.0 85.0 75.3 85.0 82.0

21.07 5.86

⌬Hs

47.7 47.5 47.8 45.4 50.5 49.5 48.5 27.7 40.2 77.0 52.9 35.8 29.5 46.0

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.63

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance 2,4-Dinitrophenol 2,6-Dinitrophenol 1,1-Dinitropropane 1,3-Dioxane 1,4-Dioxane ⌬Ht ⫽ 2.4⫺0.3 1,3-Dioxolane Diphenylamine Diphenyl carbonate Diphenyl disulfide Diphenyl disulfone Diphenylenimine 1,2-Diphenylethane 1,1-Diphenylethylene Diphenyl ether 6,6-Diphenylfulvene Diphenylmercury Diphenylmethane 1,3-Diphenyl-2-propanone Diphenyl sulfide Diphenyl sulfone Diphenyl sulfoxide 1,2-Dipropoxyethane Dipropylamine Dipropyl disulfide Dipropyl ether Dipropylmercury Dipropyl sulfate Dipropyl sulfide Dipropyl sulfite Dipropyl sulfone Dipropyl sulfoxide Divinyl ether Divinyl sulfone Dodecane Dodecanedioic acid Dodecanenitrile Dodecanoic acid Dodecanol 1-Dodecene ⌬Ht ⫽ 4.6⫺60.2 1,2-Epoxybutane 1,2-Epoxypropane Ergosterol Ethane Ethane-d6 1,2-Ethanediamine 1,2-Ethanediol 1,2-Ethanediol diacetate 1,2-Ethanedithiol

⌬Hm

12.85

⌬Hv

⌬Hs

34.4 34.2

104.6 112.1 62.5 39.1 38.6

27.48 17.86 23.4

51.5 17.22

48.2

18.2

13.8 8.83

33.5 41.9 31.3

12.1

36.6

36.55

44.5

36.64 31.4 17.42

63.5 44.0

35.6 89.1 90.0 95.0 161.9 84.5 91.4 73.2 67.0 104.6 112.8 67.5 89.1 67.8 106.3 97.1 50.6 40.0 54.1 35.7 55.2 66.9 44.2 58.6 79.9 74.5 26.2 56.5 61.5 153.1 76.1 132.6 92.0 60.8

400 K

600 K

800 K

1000 K

126.5

181.8

218.2

243.3

186.2 196.2

298.3 262.0

350.2 311.3

390.0 348.0

201.7

272.5

328.2

372.6

356.2

481.3

572.2

656.5

341.8

460.0

545.6

608.8

65.5 81.7

89.3 108.5

108.0 127.4

122.6 140.5

113.2

136.9

166.9

30.3 21.6 2.86

14.7

118.4 5.2

22.58 11.23

38.0 50.5 45.5 37.9

45.0 67.8 61.4 44.7

short standard long

DEAN #37261

LEFT

(McGHP)

6.64

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance Ethanethiol Ethanol Ethanolamine Ethoxybenzene 2-Ethoxyethanol 2-(2-Ethoxyethoxy)ethanol 2-(2-Ethoxyethoxy)ethyl acetate 2-Ethoxyethyl acetate 1-Ethoxy-2-methoxyethane N-Ethylacetamide Ethyl acetate Ethyl acrylate Ethylamine N-Ethylaniline Ethylbenzene 2-Ethylbenzoic acid 3-Ethylbenzoic acid 4-Ethylbenzoic acid 2-Ethyl-1-butanol Ethyl butanoate 2-Ethylbutanoic acid 2-Ethyl-1-butene Ethyl trans-2-butenoate Ethyl chloroacetate Ethyl 4-chlorobutanoate Ethyl chloroformate Ethyl trans-cinnamate Ethyl crotonate Ethyl cyanoacetate Ethylcyclobutane Ethylcyclohexane 1-Ethylcyclohexene Ethylcyclopentane 1-Ethylcyclopentene Ethyl dichloroacetate Ethyl 2,2-dimethylpropanoate Ethylene Ethylene-d4 Ethylene carbonate 2,2⬘-(Ethylenedioxy)bis(ethanol) Ethylene glycol (see 1,2-Ethanediol) Ethylene glycol diacetate Ethylene oxide Ethylenimine N-Ethylformamide Ethyl formate 2-Ethylhexanal 2-Ethylhexane Ethyl hexanoate 2-Ethylhexanoic acid

⌬Hm

⌬Hv

⌬Hs

400 K

600 K

800 K

1000 K

4.98 5.02 20.50

26.8 38.6 49.8 40.7 39.2 47.5 91.2

27.3 42.3

88.2 81.2

113.9 107.7

133.2 127.2

148.0 141.9

137.4

182.6

213.4

234.5

90.6

119.6

141.8

158.5

170.5

236.1

281.0

312.8

170.3

228.0

269.5

300.8

215.9

310.0

377.0

423.8

183.6

258.2

314.7

356.3

53.1 63.9

70.7 82.3

83.8 95.6

93.9 104.9

62.6 70.4

86.3 98.6

102.9 117.7

114.9 131.6

34.3 10.48

9.18

31.9 34.7 28.0 35.6

43.2 35.5 51.2 28.8 40.4

51.0 48.2

52.7 39.8 64.9 35.6 26.6 52.3 42.2 100.7 99.1 97.5 63.2 42.7 31.1 44.4 49.5 52.7 42.3

58.6 44.3

8.33 6.9

3.35

64.4 28.7 34.0 32.0 38.5 34.5 13.5

13.19

50.1 71.4

5.2

25.5 30.3

9.20

29.9 33.6 56.0

31.2 40.6 43.3 36.4 50.6 41.2

73.2 79.1 61.4 24.8 34.6 58.4 32.0 49.0 39.6 51.7 75.6

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.65

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance 2-Ethyl-1-hexanol 2-Ethylhexyl acetate 2-Ethyl hydroperoxide Ethylidenecyclohexane Ethylidenecyclopentane Ethyl isocyanide Ethyl isopentanoate Ethyl isopentyl ether Ethylisopropylamine Ethyl isopropyl ether Ethyl isopropyl sulfide Ethyl lactate Ethyllithium Ethylmercury bromide Ethylmercury chloride Ethylmercury iodide 1-Ethyl-2-methylbenzene 1-Ethyl-3-methylbenzene 1-Ethyl-4-methylbenzene Ethyl 2-methylbutanoate Ethyl 3-methylbutanoate 2-Ethyl-3-methyl-1-butene 1-Ethyl-1-methylcyclopentane Ethyl methyl ether 3-Ethyl-2-methylpentane 3-Ethyl-3-methylpentane 3-Ethyl-2-methyl-1-pentene Ethyl 2-methylpropanoate Ethyl methyl sulfide Ethyl nitrate 1-Ethyl-2-nitrobenzene 1-Ethyl-4-nitrobenzene 3-Ethylpentane Ethyl pentanoate Ethyl pentyl ether 2-Ethylphenol 3-Ethylphenol 4-Ethylphenol Ethylphosphonic acid Ethylphosphonic dichloride Ethyl propanoate Ethyl propyl ether Ethyl propyl sulfide Ethyl trichloroacetate S-Ethyl thiolacetate Ethyl 2-vinylacrylate Ethyl vinyl ether Fluoranthrene 9H-Fluorene Fluorobenzene

⌬Hm

⌬Hv 45.2 43.5

⌬Hs

400 K

600 K

800 K

1000 K

202.9 198.7 197.5

275.3 273.6 272.0

326.8 325.5 324.7

363.6 363.2 362.2

109.1

144.7

172.3

193.2

116.4 120.2

152.3 155.1

179.6 178.7

200.6 195.4

211.0

285.9

340.7

381.6

173.3

232.7

279.0

315.6

125.5

171.0

200.1

220.0

48.1 43.1 42.0

18.1 33.5 8.7

8.7

10.0 7.6 13.4

43.9 33.0 29.9 28.2 32.7 46.4

38.9 38.5 38.4 37.0

11.34 10.84

33.2 26.7 32.9 32.8

9.8 8.5

33.7 29.5 33.1

9.55

31.1 37.0 34.4

10.6

33.9 28.9 34.2

34.4

40.0

18.87 19.58 11.31

39.0 33.1 30.1 37.8 49.4 116.7 76.6 76.1 79.5 47.7 46.9 46.6 44.4 43.9 34.5 38.9 38.5 38.0 37.5 39.8 31.9 36.3 59.8 62.8 35.2 47.0 41.0 63.6 68.2 80.3 50.6 42.7 39.2 31.4 40.0 51.0

26.2

48.5 26.6 99.2

31.2

34.6

short standard long

DEAN #37261

LEFT

(McGHP)

6.66

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance 4-Fluorobenzoic acid Fluoroethane Fluoromethane 1-Fluorooctane 1-Fluoropropane 2-Fluoropropane 2-Fluorotoluene 4-Fluorotoluene Fluorotrichloromethane Fluorotrinitromethane Formaldehyde Formamide Formic acid Formyl fluoride Fumaric acid Fumaronitrile Furan, ⌬Ht ⫽ 2.1⫺123.2 2-Furancarboxaldehyde 2-Furancarboxylic acid Furanmethanol Glutaric acid Glycerol Glyceryl triacetate Glyceryl tributanoate Glyceryl trinitrate Heptadecane, ⌬Ht ⫽ 11.011.1 Heptadecanoic acid 1-Heptadecene 1-Heptanal Heptane 1-Heptanenitrile 1-Heptanethiol Heptanoic acid 1-Heptanol 2-Heptanol 3-Heptanol 2-Heptanone 4-Heptanone 1-Heptene, ⌬Ht ⫽ 0.3⫺136 trans-2-Heptene Heptylamine Heptyl methyl ether Hexachlorobenzene Hexachloroethane, ⌬Ht ⫽ 8.071.3 Hexadecafluoroethylcyclohexane Hexadecafluoroheptane Hexadecane Hexadecanoic acid 1-Hexadecanol, ⌬Ht ⫽ 16.634 1-Hexadecene

⌬Hm

⌬Hv

⌬Hs

400 K

600 K

800 K

1000 K

74.1 44.2

98.6 57.9

116.4 68.8

129.7 77.2

102.7 103.5

137.3 138.7

162.7 163.8

181.5 182.2

152.4

207.9

245.2

271.3

39.2(g)

48.2

55.9

62.0

53.8 46.4

67.0 56.2

76.8 63.1

83.5 67.9

88.7

122.6

164.9

158.5

501.4

676.8

803.7

897.9

486.9 213.4 211.0

655.5 283.3 285.9

777.1 333.9 340.7

866.9 371.1 381.6

233.5

312.1

372.0

418.4

224.4

300.9

357.0

392.5

196.5

264.6

314.1

351.0

201.2 151.5

233.4 166.6

250.9 173.6

260.8 177.3

472.3

687.7

757.4

846.0

485.7 457.9

652.7 616.4

773.6 731.82

863.2 815.0

91.2 16.7 40.4

9.4

35.4 34.1 25.0

49.7

39.4 34.7

23.3 6.69 12.7

22.7 21.7

3.80 14.35

27.1 43.2

13.13 20.9 18.28

53.6

21.87 40.5 58.8 31.4 23.6 14.16

61.0

52.9 51.8 31.8

25.4

39.8

13.2

48.1 49.8 42.5 38.3 36.2 31.1

12.66 11.72

23.85 9.8

51.8 42.04 34.29 30.2

45.9

51.2

50.4

60.2 20.1 136.0 72.0 27.5 50.6 108.5 64.4 85.8 85.7 107.1 100.0 86.0 85.0 47.7 36.6 51.9 50.6 74.0 66.8

47.2 35.5 50.0 46.9 92.6 59.0 38.5 36.4 81.4 154.4 169.5 80.3

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.67

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance Hexadienoic acid Hexafluoroacetone Hexafluoroacetylacetone Hexafluorobenzene Hexafluoroethane, ⌬Ht ⫽ 3.7⫺169.2 cis-Hexahydroindane trans-Hexahydroindane Hexamethylbenzene ⌬Ht ⫽ 1.1⫺156.7 ⌬Ht ⫽ 1.8110.7 1,1,1,3,3,3-Hexamethyldisilazane Hexamethyldisiloxane Hexamethylphosphoric triamide Hexanal Hexanamide Hexane 1,6-Hexanedioic acid 1,6-Hexanediol Hexanenitrile 1-Hexanethiol Hexanoic acid 1-Hexanol 2-Hexanol 3-Hexanol 2-Hexanone 3-Hexanone 1-Hexene cis-2-Hexene trans-2-Hexene cis-3-Hexene trans-3-Hexene Hexylamine Hexyl methyl ether 1-Hexyne Hydrazine 2-Hydroxybenzaldehyde 2-Hydroxybenzoic acid 2-Hydroxy-2,4,6-cycloheptatrienone 2-Hydroxy-1-isopropyl-4-methylbenzene 4-Hydroxy-4-methyl-2-pentanone 3-Hydroxypropanonitrile 2-Hydroxypyridine 3-Hydroxypyridine 4-Hydroxypyridine 8-Hydroxyquinoline Icosane Icosanoic acid 1-Icosene Indane Indene

⌬Hm

⌬Hv

⌬Hs

19.8 27.1 31.7 16.2

21.3 30.6 35.7

400 K

600 K

800 K

1000 K

183.6 125.6

219.9 149.0

241.1 160.7

253.7 166.8

310.4

406.4

474.9

525.3

184.2

243.9

287.4

319.7

181.9

246.8

294.4

330.1

204.5

273.1

325.1

366.7

195.3

261.8

310.7

346.9

167.5 161.5 166.1 161.1 168.2

225.5 221.8 223.4 222.6 225.5

267.9 165.3 266.1 265.7 267.4

299.3 297.9 297.9 297.9 298.7

158.5

207.5

243.3

270.1

588.5

794.0

942.6

1052.7

574.0

772.7

916.0

1021.7

13.6

11.58 2.7

20.6

48.2

57.5 56.1 74.7

41.4 37.2 14.28 25.1 13.08 34.85 25.5 18.0(1) 15.40 15.40 44.3 14.90 13.49 9.35 8.86 8.26 8.25 11.08

12.7

28.9

38.0 37.2 71.1 44.5 41.0 46.0 36.4 35.4 28.3 29.1 28.9 28.7 28.9 36.5 34.9

43.1 42.5 30.6 32.2 31.6 31.4 31.7 45.1 42.1

45.3 38.2

28.5 56.1

69.88 72.0 34.3

98.7 31.6 129.3 83.3 47.9 45.8 72.2 61.6 58.5

57.5 55.9 39.6

95.1 83.7 91.2 47.7 86.6 88.3 103.8 108.8 100.8 199.6 99.8 48.8 52.9

short standard long

DEAN #37261

LEFT

(McGHP)

6.68

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance Indole Iodobenzene Iodobenzoic acid 1-Iodobutane 2-Iodobutane Iodocyclohexane Iodoethane 1-Iodohexane Iodomethane 1-Iodo-2-methylpropane 2-Iodo-2-methylpropane 1-Iodonaphthalene 2-Iodonaphthalene 1-Iodopentane 1-Iodopropane 2-Iodopropane 3-Iodo-1-propene 2-Iodotoluene (also 3-, 4-) Isobutanonitrile Isobutyl acetate Isobutylamine Isobutylbenzene Isobutylcyclohexane Isobutyl dichloroacetate Isobutyl formate Isobutyl isobutanoate Isobutyl isopropyl ether Isobutyl methyl ether Isobutyl propyl ether Isobutyl trichloroacetate Isobutyl vinyl ether 2-Isopropoxyethanol Isopropyl acetate Isopropylamine Isopropylbenzene Isopropylcyclohexane Isopropylcyclopentane Isopropylmethylamine 1-Isopropyl-2-methylbenzene 1-Isopropyl-3-methylbenzene 1-Isopropyl-4-methylbenzene Isopropyl methyl ether 2-Isopropyl-5-methylphenol Isopropyl methyl sulfide Isopropyl nitrate Isopropylpropylamine Isopropyl propyl sulfide Isopropyl trichloroacetate Isoquinoline Ketene

⌬Hm

⌬Hv

9.76

39.5 34.7 33.3 29.4

14.5

27.3 33.5 31.4

32.1 30.7

12.51

32.4 35.9 30.6 37.8

33.6 38.2 31.6 28.0 28.3

7.33 7.79

10.0 13.7 9.7

30.7 40.4 32.9 27.8 37.5 33.6 28.7 38.4 38.1 38.2 26.1

9.4

30.7 34.9 32.1 35.1

7.45

49.0

⌬Hs 69.9 47.7 87.9 40.6 38.5 47.3 31.9 49.8 28.0 38.8 35.4 72.4 90.8 45.3 36.2 34.1 38.1 54.4 37.2

400 K

600 K

800 K

1000 K

130.1

173.3

201.1

220.1

80.3

103.1

119.9

132.4

51.6

63.9

73.1

80.2

148.8

191.7

221.1

242.3

109.9 111.2

142.7 144.7

166.5 168.2

184.2 185.5

119.5

156.4

183.0

202.5

200.8

277.0

328.9

365.3

138.0

184.8

220.4

247.2

145.1 150.5

192.5 195.9

229.9 226.5

260.6 247.9

59.5

70.7

78.7

86.4

33.9 47.9 47.6 52.3 46.4 36.6 30.1 30.3 53.1 34.6 50.1 37.2 28.4 45.1 44.0 39.4 30.9 50.6 50.0 50.2 26.4 91.2 34.2 38.8 37.2 41.8 51.9 60.3 20.4

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.69

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance (⫺)-Leucine (⫹)-Limonene Maleic acid Maleic anhydride Malononitrile D-Mannitol Methacrylonitrile Methane Methane-d4 Methanethiol, ⌬Ht ⫽ 0.22⫺135.6 Methanol, ⌬Ht ⫽ 0.6⫺115.8 4-Methoxybenzaldehyde Methoxybenzene 2-Methoxybenzoic acid 3-Methoxybenzoic acid 4-Methoxybenzoic acid 3-Methoxy-1-butanol 2-Methoxyethanol 2-(2-Methoxyethoxy)ethanol 2-Methoxyethyl acetate 2-Methoxy-1-propoxyethane 2-Methoxytetrahydropyran 1-Methoxy-2,4,6-trinitrobenzene N-Methylacetamide Methyl acetate Methyl acetoacetate Methyl acrylate Methylamine 4-Methylaniline Methyl benzoate 2-Methylbenzoic acid 3-Methylbenzoic acid 4-Methylbenzoic acid 1-Methylbicyclo[4.1.0]heptane 1-Methylbicyclo[3.1.0]hexane 2-Methyl-1,3-butadiene 3-Methyl-1,3-butadiene 2-Methylbutane 3-Methylbutanenitrile 2-Methylbutanethiol 3-Methyl-1-butanethiol 2-Methyl-2-butanethiol ⌬Ht ⫽ 8.0⫺114.0 Methyl butanoate 2-Methylbutanoic acid 3-Methylbutanoic acid 2-Methyl-1-butanol 3-Methyl-1-butanol 2-Methyl-2-butanol, ⌬Ht ⫽ 2.0⫺127.2 3-Methyl-2-butanol

⌬Hm

⌬Hv

⌬Hs

400 K

600 K

800 K

1000 K

40.5 48.6 58.7 51.4

52.2 63.4 73.5 67.0

62.9 74.8 85.0 79.7

71.8 83.0 94.1 89.5

60.2

78.9

93.9

105.7

133.1 129.7 152.7

173.2 168.6 208.7

200.8 197.5 249.8

221.3 219.2 280.8

179.0

236.7

279.4

308.8

150.6 48.1 110.0 71.5 79.1 22.6 0.94 5.91 3.18

31.8 8.2 24.6 35.2 56.8 39.0

50.8 37.5 46.6 43.9 36.3

9.72

6.13 18.22 9.74 20.17 15.72 22.73

4.79 5.15

7.5 0.6

4.45

45.2 50.3 43.7 42.7 133.1

59.4 30.3 36.0 33.1 25.6

29.2 24.4

43.2

55.6

31.1 25.9 27.2 24.7 35.1 33.8 31.4 33.8

7.32

23.8 37.4 64.5 46.9 104.7 107.4 109.8

43.2 45.2 44.1 39.0 41.8

32.3

39.2 34.8 26.8 28.0 24.9 41.7 39.5 39.4 35.7 39.3 46.9 57.5 55.2 55.6 50.1 53.0

short standard long

DEAN #37261

LEFT

(McGHP)

6.70

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance 3-Methyl-2-butanone 2-Methyl-1-butene 3-Methyl-1-butene 2-Methyl-2-butene Methyl 2-butenoate 3-Methyl-1-butyne 2-Methylbutyl acetate Methyl chloroacetate Methyl cyanoacetate Methyl cyclobutanecarboxylate Methylcyclohexane 1-Methylcyclohexanol cis-2-Methylcyclohexanol trans-2-Methylcyclohexanol cis-3-Methylcyclohexanol trans-3-Methylcyclohexanol cis-4-Methylcyclohexanol trans-4-Methylcyclohexanol 1-Methylcyclohexene Methylcyclopentane 1-Methyl-1-cyclopentene 3-Methyl-1-cyclopentene 4-Methyl-1-cyclopentene Methyl cyclopropanecarboxylate 2-Methyldecane 4-Methyldecane Methyl decanoate Methyl dichloroacetate Methyldichlorosilane Methyl 2,2-dimethylpropanoate 2-Methyl-1,3-dioxane 4-Methyl-1,3-dioxane 4-Methyl-1,3-dioxolan-2-one Methyl dodecanoate N-Methylethanediamine 1-Methylethyl acetate 1-Methylethyl thiolacetate N-Methylformamide Methyl formate Methyl 2-furancarboxylate Methylglyoxal 2-Methylheptane 3-Methylheptane 4-Methylheptane Methyl heptanoate 2-Methylhexane 3-Methylhexane Methyl hexanoate 5-Methyl-1-hexene cis-3-Methyl-3-hexene

⌬Hm

⌬Hv

⌬Hs

7.9 5.4 7.6

32.4 25.5 24.1 26.3

36.8 25.9 23.8 27.1 41.0 25.8

6.75

6.93

26.2 37.5 39.2 48.2 37.1 31.3 79.0 48.5 53.0

29.1

35.3 40.3 40.7 39.3 33.4

46.7 61.7 44.7 35.4 80 63.2 63.2 65.3 65.3 65.7 66.1 37.9 31.6 32.6 31.0 32.2 41.3 54.3 53.8 66.7 47.7 28.0 38.8 38.6 39.2

400 K

600 K

800 K

1000 K

138.9 147.5 133.6

187.1 192.1 181.7

222.4 225.3 217.8

248.7 250.3 245.0

130.1

169.9

198.3

219.2

185.6

269.7

329.5

371.5

151.1 136.0 136.4 136.4

219.4 195.8 197.1 196.7

267.8 238.5 239.3 238.4

303.1 269.0 269.9 269.5

81.6

105.4

121.8

133.9

211.0 212.0

285.9 285.9

340.7 340.7

381.6 381.6

9.62 37.6 32.9 35.7 7.45

27.9

11.88 11.38 10.84

33.3 33.7 33.4

8.87

30.6 30.9 38.6

77.2 45.2 37.3 42.3 56.2 28.4 45.2 38.1 39.7 39.8 39.7 51.6 34.9 35.1 48.0 34.3 36.5

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.71

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance trans-3-Methyl-3-hexene Methylhydrazine Methyl isobutanoate Methyl isocyanide 1-Methyl-4-isopropylbenzene 3-Methylisoxazole 5-Methylisoxazole Methylmercury bromide Methylmercury chloride Methylmercury iodide Methyl methacrylate Methyl 2-methylbutanoate Methyl-3-methylbutanoate 1-Methylnaphthalene ⌬Ht ⫽ 5.0⫺32.4 2-Methylnaphthalene ⌬Ht ⫽ 5.615.4 Methyl nitrate Methyl nitrite 1-Methyl-4-nitrobenzene 2-Methylnonane 3-Methylnonane 5-Methylnonane 2-Methyloctane Methyl octanoate Methyl oxirane 2-Methylpentane 3-Methylpentane 2-Methyl-2,4-pentanediol 3-Methylpentanenitrile Methyl pentanoate 2-Methylpentanoic acid 2-Methyl-1-pentanol 2-Methyl-2-pentanol 2-Methyl-3-pentanol 3-Methyl-1-pentanol 3-Methyl-2-pentanol 4-Methyl-1-pentanol 4-Methyl-2-pentanol 3-Methyl-3-pentanol 2-Methyl-3-pentanone 3-Methyl-2-pentanone 4-Methyl-2-pentanone 2-Methyl-1-pentene 3-Methyl-1-pentene 4-Methyl-1-pentene 2-Methyl-2-pentene cis-3-Methyl-2-pentene trans-3-Methyl-2-pentene cis-4-Methyl-2-pentene

⌬Hm

⌬Hv

⌬Hs

10.4

36.1 32.6

35.9 40.4 37.3 30.8

9.60

400 K

600 K

800 K

1000 K

212.3

292.0

345.1

381.6

38.2

36.0

41.0 41.0 67.8 64.4 65.3 60.7 41.8 41.0

6.94

45.5

11.97

46.0

61.7

211.2

290.0

343.2

381.2

8.2

31.6 20.9

32.1 22.6 79.1 49.6 49.7 49.3

91.5 76.3

115.2 97.7

131.7 112.8

143.1 123.5

184.1 181.9

211.7 246.9

296.2 294.6

331.4 330.1

170.7 177.8 162.8 163.2 163.2 163.2 167.6

227.6 232.6 221.3 222.6 222.6 222.6 226.4

269.5 272.8 264.0 245.2 265.3 265.3 267.8

300.4 302.5 296.2 297.5 297.5 297.5 299.2

38.2 38.3 38.1 18.00

6.27 5.30

27.4 27.8 28.1 57.3 35.1 35.4 52.1 50.2 39.6 41.8 46.3 43.4 44.5 44.2 41.8 33.8 34.2 34.5 28.1 26.9 27.1 29.0 28.8 29.3 27.6

56.4 27.9 29.9 30.3 41.6 43.1 57.5 55.7 54.8 54.4 62.3 56.9 60.5 50.6 39.8 40.5 40.6 30.5 28.7 28.7 31.6 31.2 31.5 29.5

short standard long

DEAN #37261

LEFT

(McGHP)

6.72

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance trans-4-Methyl-2-pentene 4-Methyl-3-penten-2-one Methyl pentyl ether Methyl pentyl sulfide 3-Methyl-1-phenyl-1-butanone 2-Methyl-1-phenylpropane Methyl phenyl sulfide Methyl phenyl sulfone Methylphosphonic acid 2-Methylpiperidine 2-Methylpropanal 2-Methylpropane 2-Methylpropanenitrile 2-Methyl-1-propanethiol 2-Methyl-2-propanethiol ⌬Ht ⫽ 4.1⫺121.6 ⌬Ht ⫽ 0.7⫺116.2 ⌬Ht ⫽ 1.0⫺73.8 Methyl propanoate 2-Methylpropanoic acid 2-Methyl-1-propanol 2-Methyl-2-propanol ⌬Ht ⫽ 0.813 2-Methylpropene Methyl propyl ether Methyl propyl sulfide 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 1-Methyl-1H-pyrrole Methyl salicylate ␣-Methylstyrene cis-␤-Methylstyrene trans-␤-Methylstyrene Methyl tetradecanoate 2-Methylthiacyclopentane 4-Methylthiazole 2-Methylthiophene 3-Methylthiophene Methyl trichloroacetate Methyl tridecanoate Methyl undecanoate 5-Methyluracil Morpholine Naphthalene 1-Naphthalenecarboxylic acid 2-Naphthalenecarboxylic acid 1-Naphthol 2-Naphthol 1,4-Naphthoquinone

⌬Hm

12.5

4.66 5.0 2.5

⌬Hv

⌬Hs

28.0 36.1 32.0 37.4

30.0

37.8

21.3 32.4 31.0 28.5

32.2 5.02 6.32 6.79 5.93 9.9 9.72 14.18 11.57

41.8 39.1 22.1 26.8 32.1 36.2 37.4 37.5

400 K

600 K

800 K

1000 K

171.1 214.0

229.3

269.9

300.4

203.6

272.2

324.6

366.0

36.9 45.2 59.5 49.5 54.3 92.0 48.1 40.5 31.5 19.3 37.1 34.6 30.8

124.6

169.5

202.9

227.6

147.7 151.2

193.6 199.2

225.0 232.3

247.6 256.2

35.9 35.3 50.8 46.7

142.9

189.8

222.9

247.5

111.2 138.1 144.9 133.6 133.1

147.7 183.8 191.9 186.4 186.1

175.1 218.7 227.8 222.6 222.3

196.0 244.8 255.8 243.3 247.8

187.4 187.4 189.1

254.0 254.0 256.1

300.4 300.4 301.3

333.9 333.9 334.7

123.1 122.9

165.6 164.6

194.3 192.3

214.6 211.7

180.1(g)

251.5

297.3

329.2

20.6 27.6 36.2 42.5 44.4 44.6 40.8

46.7

9.20 10.53

36.4 37.6 33.9 34.2

18.98

37.1 43.2

23.33 17.51

37.0 41.8 43.8 38.9 39.4 48.3 82.7 71.4 134.1 44.0 72.6 110.4 113.6 91.2 94.2 72.4

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.73

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance 1-Naphthylamine 2-Naphthylamine 2-Nitroaniline 3-Nitroaniline 4-Nitroaniline Nitrobenzene 1-Nitrobutane 2-Nitrobutane Nitroethane Nitromethane (Nitromethyl)benzene 2-Nitrophenol 3-Nitrophenol 4-Nitrophenol 1-Nitronaphthalene 1-Nitropropane 2-Nitropropane 2-Nitroso-1-naphthol 4-Nitroso-1-naphthol 1-Nitroso-2-naphthol 2-Nitrotoluene 3-Nitrotoluene 4-Nitrotoluene Nonadecane, ⌬Ht ⫽ 13.822.8 1-Nonadecene 1-Nonal Nonane, ⌬Ht ⫽ 6.3⫺56.0 1-Nonanethiol Nonanoic acid 1-Nonanol 2-Nonanone 5-Nonanone 1-Nonene cis-Octadecafluorodecahydronaphthalene trans-Octadecafluorodecahydronaphthalene Octadecafluoropropylcyclohexane Octadecafluorooctane Octadecane Octadecanedioic acid Octadecanoic acid Octadecanol 1-Octadecene cis-9-Octadecenoic acid Octafluorocyclobutane Octafluorotoluene Octamethylcyclotetrasiloxane Octanal Octanamide Octane 1,8-Octanedioic acid

⌬Hm

16.11 23.68 21.1 11.59

9.85 9.70

⌬Hv

40.8 38.9 36.8 38.0 34.0

⌬Hs 90.0 88.3 90.0 96.7 109 55.0 48.6 43.8 41.6 38.3 53.6

400 K

600 K

800 K

1000 K

157.5 157.4 99.0 70.3

210.1 211.1 131.6 91.7

247.0 248.7 154.0 106.9

273.6 276.0 170.2 117.9

128.5 129.2

171.0 172.3

200.7 201.8

222.0 222.8

559.4 545.0 271.1 269.0 291.6

754.9 733.7 361.5 364.1 390.3

896.3 869.7 426.4 433.3 464.6

1000.8 969.9 474.5 484.9 521.5

282.4

379.1

449.6

501.7

17.44 19.2 18.25 38.5 36.8

16.81 45.82 33.5 15.47 33.5 20.28

16.5 15.0 15.5 56.0 54.6 36.9 44.4 54.4

24.93 18.08

61.39 56.6 56.59 32.6 2.77 11.58

36.3 35.6 35.8 24.5 33.4 54.5

53.3 64.7 23.2

107.1 43.4 41.3 56.5 87.4 86.6 47.2 49.9 50.2 95.8 94.9 72.3 46.4 82.4 76.9 56.4 53.3 45.5 45.2 45.4 43.1 41.1 152.8

254.6

342.8

406.8

454.0

530.4

715.8

850.0

949.4

166.5 113.4 90.0

516.0

694.5

823.4

918.4

186.1

225.3

245.4

257.3

242.3

322.2

380.3

422.6

240.0

325.0

387.0

433.5

45.6

20.65

34.4

110.5 41.5 143.1

short standard long

DEAN #37261

LEFT

(McGHP)

6.74

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance Octanenitrile 1-Octanethiol Octanoic acid 1-Octanol (⫾)-2-Octanol (⫾)-3-Octanol 4-Octanol 2-Octanone 1-Octene 1-Octyne 2-Octyne 3-Octyne 4-Octyne Oxalic acid Oxaloyl chloride Oxamide Oxetane 2-Oxetanone 2-Oxohexamethyleneimine 4-Oxopentanoic acid 1,1⬘-Oxybis(2-ethoxy)ethane 2,2⬘-Oxybis(ethanol) Paraldehyde Pentachloroethane Pentachlorofluoroethane Pentachlorophenol Pentacyclo[4.2.0.02,5.03,8.04,7]octane Pentadecane, ⌬Ht ⫽ 9.2⫺2.25 Pentadecanoic acid 1-Pentadecene 1,2-Pentadiene cis-1,3-Pentadiene trans-1,3-Pentadiene 1,4-Pentadiene 2,3-Pentadiene Pentaerythritol Pentaerythritol tetranitrate Pentafluorobenzene Pentafluorobenzoic acid Pentafluoroethane Pentafluorophenol 2,3,4,5,6-Pentafluorotoluene Pentamethylbenzene ⌬Ht ⫽ 2.023.7 2,2,4,6,6-Pentamethylheptane Pentanal Pentanamide Pentane 1,5-Pentanediol

⌬Hm 24.3 21.36 42.30

24.42 15.57

⌬Hv

⌬Hs

41.3 42.3 58.5 46.9 44.4 36.5 40.5

56.8

34.1 35.8 37.3 36.9 36.0

40.4 42.3 44.5 43.9 42.7 98.0 31.8 113.0 29.9 47.0 83.3

28.7 16.2 9.22

54.8

52.3 11.34 1.9

36.9

81.7 71.0

58.4 57.3 41.4 45.6

400 K

600 K

800 K

1000 K

262.6

351.3

418.3

469.9

253.4

340.0

403.3

450.1

225.6 216.5

303.7 285.7

360.5 336.0

402.5 410.9

133.7

152.1

162.0

168.1

443.3

598.6

711.1

794.5

428.9 131.4 123.4 130.5 131.0 125.1

577.3 170.7 166.9 171.1 170.2 164.9

684.5 199.6 196.7 199.6 220.5 195.0

763.6 220.9 218.4 220.1

113.8

137.8

151.1

158.9

272.0

360.2

423.8

470.0

155.2

205.0

241.4

267.8

152.8

207.7

248.1

278.5

67.4

34.8 50.2 28.9

6.14

10.85

12.85 12.99 12.3

8.42

49.5 48.7 27.6 27.6 27.0 25.2 28.2 92 32.2

34.8 45.1

25.8 60.7

80.3 76.1 162.7 75.1 28.7 28.3 27.8 25.7 29.5 143.9 151.9 36.3 91.6 67.4 41.1 60.8 49.0 38.8 89.3 26.4

217.6

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.75

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance 1,5-Pentanedithiol 2,4-Pentanedione Pentanenitrile 1-Pentanethiol Pentanoic acid 1-Pentanol 2-Pentanol 3-Pentanol 2-Pentanone 3-Pentanone 1-Pentene cis-2-Pentene trans-2-Pentene cis-2-Pentenenitrile trans-2-Pentenenitrile trans-3-Pentenenitrile Pentyl acetate Pentylamine Pentylcyclohexane Pentyl propyl ether 1-Pentyne 2-Pentyne Perylene ␣-Phellandrene Phenanthrene 9,10-Phenanthrenedione Phenazine Phenol Phenyl acetate Phenylacetonitrile Phenylacetylene (⫺)-3-Phenyl-1-alanine ␣-Phenylbenzeneacetic acid Phenyl benzoate Phenylboron dichloride Phenylcyclopropane N-Phenyldiacetimide Phenyl formate Phenylhydrazine 1-Phenyl-1-propanone 1-Phenyl-2-propanone Phenyl salicylate Phenyl vinyl ether Phthalamide 1,3-Phthalic acid 1,4-Phthalic acid Phthalic anhydride Phthalonitrile Piperidine Propadiene

⌬Hm

4.73 17.5 14.16 9.83

10.63 11.59 5.81 7.12 8.36

⌬Hv 34.3 36.1 34.9 44.1 44.4 41.4 43.5 33.4 33.5 25.2 26.1 26.1 36.4 37.8 37.1 41.0 34.0 35.0 27.7 29.3

⌬Hs 59.3 41.8 43.6 41.2 62.4 57.0 54.2 54.0 38.4 38.5 25.5 26.9 26.8 43.2 44.9 44.8 40.1 53.9 42.8 28.4 30.8

400 K

600 K

800 K

1000 K

175.4

234.0

279.4

315.1

166.3

222.8

264.4

295.4

152.4

202.2

239.0

266.1

138.5 132.1 136.7

186.4 182.5 184.2

221.5 218.8 219.5

247.7 245.9 246.1

130.1 122.2

169.0 161.9

197.1 192.1

218.4 215.1

135.8

182.2

211.8

232.2

150.4

200.9

233.4

255.9

72.0

92.1

106.4

117.2

31.75 16.46

55.7

11.29

45.7

50.6 75.5 91.6 99.9 57.8 54.8

52.9 41.8 155.2 31.27

16.43

14.85

31.7 18.6

99.0 33.9 50.2 90.0 52.9 61.7 58.5 49.0 92.1 49.9 57.3 106.7 98.3 88.7 86.9 39.3

short standard long

DEAN #37261

LEFT

(McGHP)

6.76

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance Propanal Propanamide Propane 1,2-Propanediamine 1,3-Propanediamine Propanedinitrile 1,2-Propanediol 1,3-Propanediol 1,2-Propanedione 1,2-Propanedithiol Propanenitrile, ⌬Ht ⫽ 1.7⫺96.2 1-Propanethiol, ⌬Ht ⫽ 4.0⫺131.1 2-Propanethiol 1,2,3-Propanetriol triacetate 1,2,3-Propanetriol trinitrate Propanoic acid Propanoic anhydride 1-Propanol 2-Propanol Propanolactone 2-Propenal Propene 2-Propenenitrile Propenoic acid 2-Propen-1-ol cis-1-Propenylbenzene 2-Propoxyethanol Propyl acetate 1-Propylamine Propylbenzene Propyl benzoate Propyl carbamate Propyl chloroacetate Propylcyclohexane Propylcyclopentane Propylene oxide Propyl formate Propyl nitrate Propyl propanoate Propyl trichloroacetate Propyl vinyl ether Propyne 2-Propyn-1-ol Pyrazine Pyrene Pyridazine Pyridine Pyrimidine 1H-Pyrrole Pyrrolidine, ⌬Ht ⫽ 0.5⫺66

⌬Hm 17.6 3.53

⌬Hv

⌬Hs

400 K

600 K

800 K

1000 K

28.3

29.6 85.9 14.8 44.2 50.2 79.1 58.0 37.1 38.1 49.7 36.0 31.9 29.5 85.7

96.6

126.4

148.3

164.0

94.0

128.7

154.8

174.6

88.6 116.6 118.6

114.7 153.6 154.9

134.5 182.4 181.0

149.4 205.1 200.5

108.2 112.0

144.6 149.6

171.7 176.3

192.2 195.9

80.5

108.0

128.7

144.4

95.4 187.4

126.0 254.0

147.6 300.4

163.4 333.9

119.3 200.1

159.0 275.6

188.0 327.6

210.1 364.7

247.3 212.7 92.7

350.6 297.2 125.8

423.4 361.0 149.3

474.5 407.9 166.5

149.8

194.5

225.4

247.2

72.5

91.2

105.2

115.9

106.4

149.5

177.8

197.4

114.4

168.7

206.5

233.6

19.0 40.9 54.1 57.9

5.05 5.5 5.7 21.9 10.66 5.20 5.37

3.00 6.23 11.16

10.97 9.27

10.37 10.0 6.5

31.8 29.5 27.9 57.8 32.3 41.7 41.4 39.9 28.3 18.4

32.1 52.6 47.4 45.4 47.0 31.3 14.2

40.0

47.3

41.4 33.9 29.6 38.2 49.8

52.1 39.7 31.3 46.2 51.9 81.2 48.5 45.1 41.1 28.3 37.5 40.6 43.5 53.1 29.3

36.1 34.7 27.4 33.6 35.9 35.5

22.1 42.1 56.3 17.11 8.28 7.91 8.58

35.1 49.8 38.8 33.0

53.5 40.2 50.0 45.1 37.6

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.77

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance Quinoline Salicylic acid 5,5⬘-Spirobis(1,3-dioxane) Spiro[2.2]pentane cis-Stilbene trans-Stilbene Styrene Succinic acid Succinic anhydride Succinonitrile p-Terphenyl 1,1,2,2-Tetrabromoethane Tetrabromomethane Tetrabutyltin Tetracene Tetrachloro-1,4-benzoquinone 1,1,2,2-Tetrachloro-1,2-difluoroethane 1,1,1,2-Tetrachloro-2,2-fluorooctane 1,1,1,2-Tetrachloroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetrachloromethane ⌬Ht ⫽ 4.6⫺47.9 Tetracyanoethylene Tetracyanomethane Tetradecane Tetradecanenitrile Tetradecanoic acid 1-Tetradecanol 1-Tetradecene Tetraethylene glycol Tetraethylgermanium Tetraethyllead Tetraethylsilane Tetraethyltin 1,1,1,2-Tetrafluoroethane Tetrafluoroethylene Tetrafluoromethane ⌬Ht ⫽ 1.5⫺196.9 Tetrahydrofuran Tetrahydrofuran-2,5-dimethanol Tetrahydrofuran-2-methanol 1,2,3,4-Tetrahydronaphthalene Tetrahydropyran Tetrahydropyran-2-methanol Tetrahydrothiophene Tetrahydrothiophene-1,1-dioxide Tetraiodomethane Tetramethoxysilane 1,2,3,4-Tetramethylbenzene

⌬Hm

⌬Hv

⌬Hs

10.66

49.7

5.8

26.8

53.9 95.1 72.8 27.5 69.0 99.2 43.9 117.5

27.4 11.0 32.95 20.41 3.92 35.5

38.7

48.7 45.1

3.70 3.99

10.56 3.28

45.6 45.38 49.0 27.6

70.0 110 19.8 125.5 98.7

400 K

600 K

800 K

1000 K

119.5

167.8

200.5

223.9

160.3

218.2

256.9

284.2

97.1

102.6

106.7

105.9

118.7 116.7 105.0 91.7

139.2 137.7 116.6 99.7

151.6 150.0 122.6 103.1

159.7 158.0 125.8 104.8

414.3

559.5

664.8

743.1

399.8

538.2

638.2

712.1

104.2 91.9 72.4

128.7 106.8 86.8

143.1 115.5 94.5

152.1 120.8 98.8

100.4

104.4

105.9

106.7

237.7

316.7

374.1

416.2

35.0

37.6 34.7 29.8

47.6

46.9 62.6

45.7 39.7 32.4 81.2 61.1 71.3 85.3 139.8 102.2 70.2 98.7 44.8 56.9

13.01 51.0 7.7 0.7

16.8 12.6

8.54

29.8 63.6 45.2 43.9 31.2 44.4 34.7

12.45

32.0 51.6 55.2 34.6 39.4

1.43

11.2

194.6 45.0

57.2

short standard long

DEAN #37261

LEFT

(McGHP)

6.78

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance 1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene 2,2,3,3-Tetramethylbutane ⌬Ht ⫽ 2.0⫺120.7 Tetramethylene sulfone Tetramethyllead 2,2,3,3-Tetramethylpentane 2,2,3,4-Tetramethylpentane 2,2,4,4-Tetramethylpentane 2,3,3,4-Tetramethylpentane Tetramethylsilane Tetramethyltin 1,1,3,3-Tetramethylurea Tetranitromethane Tetraphenylmethane Tetraphenyltin Tetrapropylgermanium Tetrapropyltin 1,2,3,4-(1H)-Tetrazole Thiacyclobutane Thiacycloheptane Thiacyclohexane ⌬Ht ⫽ 1.1⫺71.8 ⌬Ht ⫽ 7.8⫺33.1 Thiacyclopentane Thiacyclopropane Thioacetamide Thioacetic acid 1,2-Thiocresol 2,2⬘-Thiodiethanol Thiophene, ⌬Ht ⫽ 0.6⫺101.6 Thiophenol Thymol Toluene o-Toluidine m-Toluidine p-Toluidine Triacetamide 2,4,6-Triamino-1,3,5-triazine Tribromomethane Tributoxyborane Tributyl phosphate Trichloroacetic acid Trichloroacetonitrile Trichloroacetyl chloride 1,3,5-Trichlorobenzene Trichlorobenzoquinone 1,1,1-Trichloroethane ⌬Ht ⫽ 7.5⫺49.0 1,1,2-Trichloroethane

⌬Hm

⌬Hv

⌬Hs

10.7 21.0 7.54

43.8 45.5 31.4

53.7 53.4 42.9

1.4

61.5

400 K

600 K

800 K

1000 K

233.3 232.2

313.0 311.2

371.5 369.9

414.3 413.0

175.7 149.4

272.0 219.1

330.5 267.8

368.2 302.7

39.5 30.3 83.3 37.2 51.5

121.1 69.2

167.5 92.0

199.4 107.2

222.3 118.0

93.1

111.8

127.2

136.5

34.7 47.6

96.3 137.1

129.5 184.6

150.7 215.9

165.4 237.6

38.0 56.7 57.3

140.1

197.5

236.9

264.9

78.7

88.0

93.3

96.7

38.1 2.33 0.50 9.75 9.00 6.88

32.5

38.5

33.1 14.10

45.6 40.7

32.3 2.5

36.0

7.4

34.7 29.2

5.09 11.5 17.27 6.85 3.89 18.22

66.8 31.5 39.9 33.2 44.6 44.9 44.3

39.7 56.1 61.4

49.9 150.6 66.3 61.5 66.9 97.5 36.0 47.3 42.6

60.4 124.3 46.1 52.3 72.0

5.88 34.1 41.0 18.2 2.73

29.9

88.7 32.5

107.6

128.4

141.1

149.8

11.54

34.8

40.2

104.7

126.1

139.2

148.2

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.79

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance Trichloroethylene Trichloromethane Trichloromethylsilane 1,2,3-Trichloropropane 1,1,1-Trichlorotrifluoroethane 1,1,2-Trichlorotrifluoroethane 1,1,1-Trichloro-3,3,3-trifluoropropane Tricyanoethylene Tridecane, ⌬Ht ⫽ 7.7⫺18.2 Tridecanenitrile Tridecanoic acid 1-Tridecene Triethanolamine Triethoxyborane Triethoxymethane Triethylaluminum Triethylamine Triethylaminoborane Triethylarsine Triethyl arsenite Triethylbismuthine Triethylborane Triethylenediamine ⌬Ht ⫽ 9.679.8 Triethylene glycol Triethylphosphine Triethyl phosphate Triethyl phosphite Triethylstibine Trifluoroacetic acid ⌬H(dimer dissoc) ⫽ 58.8100 Trifluoroacetonitrile 1,1,1-Trifluoro-2-bromo-2-chloroethane 1,1,1-Trifluoroethane 2,2,2-Trifluoroethanol Trifluoroethylene Trifluoromethane (Trifluoromethyl)benzene Triiodomethane Triisopropylborane Triisopropyl phosphite Trimethoxyborane 1,1,1-Trimethoxyethane Trimethoxymethane 2⬘,4⬘,5⬘-Trimethylacetophenone 2⬘,4⬘,6⬘-Trimethylacetophenone Trimethylaluminum Trimethylamine Trimethyl arsenite Trimethylarsine

⌬Hm 8.8 8.94 8.9 2.47

⌬Hv

⌬Hs

400 K

600 K

800 K

1000 K

31.4 29.2

34.5 31.3

91.2 74.3

104.9 85.3

112.7 91.5

117.8 95.5

31.7

38.9

43.8

47.3

385.2

520.4

618.5

691.2

370.8

499.1

592.0

660.2

203.8

276.6

328.7

367.4

95.2

118.7

133.8

144.1

81.1 61.1 169.8 82.0

97.5 76.0 226.8 90.0

107.5 85.1 262.6 94.7

113.9 91.0 286.4 97.8

117.5

160.4

190.9

213.3

37.1 26.9 27.0 32.2

28.50

45.7

43.1 22.83 27.2

45.0 67.5

31.0

6.1 71.4

33.3

28.1 28.4 36.8 81.2 66.4 85.3 146.4 65.3 43.9 46.0 73.2 34.8 60.7 43.1 50.6 46.0 36.8 61.9 79.1 39.8 57.3 41.8 43.5 38.5

5.0 6.19

28.1 19.2 40.0

4.1 13.46 16.3

16.7 32.6

6.55

22.9

29.6

37.6 69.9 41.8 46.0 34.7 39.2 38.1 63.2 62.3 63.2 21.7 42.3 28.9

short standard long

DEAN #37261

LEFT

(McGHP)

6.80

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

cap height base of text

Cp Substance 1,2,3-Trimethylbenzene ⌬Ht ⫽ 0.7⫺54.5 ⌬Ht ⫽ 1.3⫺42.9 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene 2,6,6-Trimethylbicyclo[3.1.1]-2-heptene Trimethylbismuthine Trimethylborane 2,2,3-Trimethylbutane ⌬Ht ⫽ 2.5⫺151.8 2,3,3-Trimethyl-1-butene cis,cis-1,3,5-Trimethylcyclohexane Trimethylene oxide Trimethylene sulfide ⌬Ht ⫽ 0.7⫺96.5 Trimethylgallium 2,2,5-Trimethylhexane 2,3,5-Trimethylhexane Trimethylindium 2,4,7-Trimethyloctane 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane ⌬Ht ⫽ 7.7⫺109.0 2,3,4-Trimethylpentane 2,2,4-Trimethyl-1,3-pentanediol 2,2,4-Trimethyl-3-pentanone 2,4,4-Trimethyl-1-pentene 2,4,4-Trimethyl-2-pentene Trimethylphosphine Trimethylphosphine oxide Trimethyl phosphate 2,3,6-Trimethylpyridine 2,4,6-Trimethylpyridine Trimethylsilanol Trimethylstibine Trimethylsuccinic anhydride Trimethylthiacyclopropane Trimethyltin bromide 2,4,6-Trinitroanisole 1,3,5-Trinitrobenzene Trinitromethane 2,4,6-Trinitrophenetole 2,4,6-Trinitrotoluene 1,3,6-Trioxacycloactane 1,3,5-Trioxane Triphenylarsine Triphenylbismuthine Triphenylborane Triphenylene

⌬Hm

⌬Hv

⌬Hs

8.37

40.0

49.1

9.51

39.3 39.0

2.20

28.9

47.9 47.5 44.8 34.7 20.2 32.0

400 K

600 K

800 K

1000 K

196.2

267.8

320.9

359.4

196.5 194.2

269.0 268.1

321.9 321.5

360.2 360.1

212.7

291.3

346.1

386.3

242.9

351.2

427.6

482.0

91.6

127.4

152.3

170.2

32.2

8.3

28.7 32.3

6.2 10.00

33.7 34.4

8.62 9.04 0.86

38.2 31.9 30.8 32.1

9.27 8.6

9.53

32.4 55.7 35.6 31.4 32.6

40.0 39.9

16.7 32.6

15.11

29.9 36.0 38.1 40.2 41.4 48.5 49.9 36.9 35.1 37.3 37.7 43.3 35.8 37.5 28.0 50.2 36.8 50.6 50.3 45.6 31.4 74.1 39.3 47.3 133.1 99.6 46.7 120.5 104.7 48.8 56.6 99.3 110.9 81.6 118.0

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.81

THERMODYNAMIC PROPERTIES

TABLE 6.2 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of Organic Compounds (Continued)

top of rh base of rh cap height base of text

Cp ⌬Hm

Substance Triphenylmethane Triphenylphosphine Triphenylstibine Tripropoxyborane Tris(diethylamino)phosphine Tris(trimethylsilyl)amine Tropolone Undecane ⌬Ht ⫽ 6.9⫺36.6 Undecanenitrile Undecanoic acid 1-Undecene, ⌬Ht ⫽ 9.2⫺55.8 Uracil Urea (⫺)-Valine Vinyl acetate Vinyl benzene Vinylcyclohexane 4-Vinyl-1-cyclohexene 1,2-Xylene 1,3-Xylene 1,4-Xylene

22.32

⌬Hv

⌬Hs

41.5

100.0 96 106.3 49.4 60.7 54.4 83.7 56.4

25.9 16.99

40.9

15.1

87.9 34.4

13.61 11.55 16.81

33.5 36.2 35.7 35.7

71.1 121.3 55.4 126.5 162.8 34.8 39.6 39.7 38.3 43.4 42.7 42.4

400 K

600 K

800 K

1000 K

327.1

442.7

525.9

588.3

312.7

421.1

499.3

557.3

171.7 167.5 166.1

234.2 232.2 230.8

278.8 277.9 276.7

311.1 310.6 309.7

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds

Substance Actinium Ac Aluminum Al Al3⫹ std. state Al6BeO10 Al(BH4)3 AlBr3 std. state Al4C3 Al(CH3)3 Al(OAc)3 AlCl3 std. state AlCl3 · 6H2O AlF3 std. state

Physical State

⌬fH⬚ kJ · mol⫺1

c

0

c g aq c lq c aq c lq c c aq c c aq

0 330.0(40) ⫺538.4(15) ⫺5624 ⫺16.3 ⫺527.2 ⫺895 ⫺216 136.4 ⫺1892.4 ⫺704.2 ⫺1033 ⫺2692 ⫺1510.4(13) ⫺1531.0

⌬fG⬚ kJ · mol⫺1

0

S⬚ J · deg⫺1 · mol⫺1

56.5

0 289.4 ⫺485.3 ⫺5317 145.0 ⫺488.5 ⫺799 ⫺203 ⫺10.0

28.30(10) 164.554(4) ⫺325.(10) 175.6 289.1 180.2 ⫺74.5 89 209.4

⫺628.8 ⫺878 ⫺2269 ⫺1431.1 ⫺1322

109.29 ⫺152.3 377 66.5(5) ⫺363.2

C⬚p J · deg⫺1 · mol⫺1

27.2 24.4 21.4 265.19 194.6 100.58

155.6 91.13

75.13

short standard long

DEAN #37261

LEFT

(McGHP)

6.82

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance AlF3 · H2O AlH3 AlI3 std. state AlK(SO4)2 · 12H2O AlN Al(NO3)3 std. state Al(NO3)3 · 6H2O Al(NO3)3 · 9H2O AlO⫺2 std. state Al2O3 corundum Al(OH)3 Al(OH)⫺4 std. state AlP AlPO4 berlinite Al2S3 Al2Se3 Al2SiO5 andalusite Al2(SO4)3 std. state Al2Te3 Americium Am Am3⫹ Am4⫹ Am2O3 AmO2 Ammonium NH3 undissoc; std. state ND3 NH⫹4 std. state NH4OH undissoc; std. state ionized; std. state NH4OAc std. state NH4Al(SO4)2 std. state NH4AsO2 std. state NH4H2AsO3 std. state NH4H2AsO4 std. state (NH4)2HAsO4 std. state (NH4)3AsO4 std. state NH4Br std. state NH4BrO3 NH4 carbamate NH4Cl std. state NH4ClO3 std. state

Physical State

⌬fH⬚ kJ · mol⫺1

c c c aq c c aq c c aq c c aq c c c c c c aq c

⫺2297 ⫺46.0 ⫺313.8 ⫺699 ⫺6061.8 ⫺318.1 ⫺1155 ⫺2850.5 ⫺3757.1 ⫺930.9 ⫺1675.7(13) ⫺1284 ⫺1502.5 ⫺166.5 ⫺1733.8 ⫺724.0 ⫺565 ⫺2592.0 ⫺3435 ⫺3790 ⫺326

c aq aq c c

0 ⫺682.8 ⫺511.7 ⫺1757 ⫺1005.0

g aq g aq aq aq c aq c aq aq c c aq aq aq c aq aq c c aq aq

⫺45.94(35) ⫺80.29 ⫺58.6 ⫺133.26(25) ⫺361.2 ⫺362.50 ⫺616.14 ⫺618.52 ⫺2352.2 ⫺2481 ⫺561.54 ⫺847.30 ⫺1059.8 ⫺1042.07 ⫺1171.1 ⫺1286.7 ⫺271.8 ⫺254.05 ⫺199.58 ⫺657.60 ⫺314.5 ⫺299.66 ⫺236.48

⌬fG⬚ kJ · mol⫺1 ⫺2052 ⫺300.8 ⫺640 ⫺5141.7 ⫺287.0 ⫺820 ⫺2203.9 ⫺2929.6 ⫺830.9 ⫺1582.3 ⫺1306 ⫺1305.3 ⫺1618.0 ⫺640

S⬚ J · deg⫺1 · mol⫺1 209 30.0 159.0 12.1 687.4 20.14 117.6 467.8 569 ⫺36.8 50.92(10) 71 102.9 90.79 116.85

⫺2444.8 ⫺3507 ⫺3205

93.2 239.3 ⫺583.3

0 ⫺671.5 ⫺461.1 ⫺1678 950.2

62.7 ⫺159.0 ⫺372 154.7 96.2

⫺16.4 ⫺26.57 ⫺26.0 ⫺79.37 ⫺254.0

192.776(5) 111.3 203.9 111.17(40) 165.5

⫺236.65

102.5

⫺448.78 ⫺2038.4 ⫺2054 ⫺429.41 ⫺666.60 ⫺833.0 ⫺832.66 ⫺873.20 ⫺886.63 ⫺175.2 ⫺183.34 ⫺60.84 ⫺448.07 ⫺202.9 ⫺210.62 ⫺87.40

200.0 216.3 ⫺168.2 154.8 223.8 172.05 230.5 225.1 177.4 113.0 194.97 275.10 133.5 94.6 169.9 275.7

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

40.2 98.7 651.0 30.10 433.0

79.15 93.1

93.18 105.06 122.76 259.4

35.65 38.23 79.9

⫺68.6 73.6 226.44

151.17

96.0 ⫺61.9

84.1 ⫺56.5

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.83

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance NH4ClO4 std. state NH4CN std. state NH4CNO cyanate std. state (NH4)2CO3 std. state (NH4)2C2O4 oxalate (NH4)2CrO4 std. state (NH4)2Cr2O7 NH4 dithiocarbonate NH4F std. state NH4 formate std. state NH4HCO3 NH4I std. state NH4IO3 std. state NH4N3 azide NH4NO2 NH4NO3 std. state NH4H2PO4 std. state (NH4)2HPO4 std. state NH4H3P2O7 NH4HS NH4HSO3 NH4HSO4 std. state (NH4)3PO4 std. state (NH4)4P2O7 std. state (NH4)2PtCl6 NH4ReO4 (NH4)2S NH4SCN NH4HSeO4 std. state (NH4)2SeO4 (NH4)2SiF6 (NH4)2SO3 (NH4)2SO4 std. state (NH4)2S2O8 std. state NH4VO3

Physical State

⌬fH⬚ kJ · mol⫺1

c aq c aq aq

⫺295.3 ⫺261.84 0.4 18.0 ⫺278.7

aq c c aq aq c c aq aq c aq c aq c aq c aq aq c aq c aq c aq aq c aq aq c aq c aq aq c c aq aq aq aq c aq c aq c aq c

⫺942.15 ⫺1123.0 ⫺1167.3 ⫺1144.3 ⫺1755.2 ⫺126.8 ⫺463.96 ⫺465.14 ⫺558.06 ⫺849.4 ⫺824.5 ⫺201.4 ⫺187.69 ⫺385.8 ⫺354.0 115.5 142.7 ⫺237.2 ⫺365.56 ⫺339.87 ⫺1145.07 ⫺1428.79 ⫺1556.91 ⫺1557.16 ⫺2409.1 ⫺156.9 ⫺150.2 ⫺758.7 ⫺1026.96 ⫺1019.85 ⫺1671.9 ⫺1674.9 ⫺2801.2 ⫺803.3 ⫺945.6 ⫺231.8 ⫺56.1 ⫺714.2 ⫺864.0 ⫺2681.69 ⫺900.4 ⫺1180.9 ⫺1174.28 ⫺1648.08 ⫺1610.0 ⫺1053.1

⌬fG⬚ kJ · mol⫺1 ⫺88.8 ⫺87.99

S⬚ J · deg⫺1 · mol⫺1 186.2 295.4

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1 128.1 134.0

92.9 ⫺177.0

207.5 220.1

⫺686.64

169.9 226.0

⫺886.59 ⫺1459.5

277.0 488.7

⫺348.78 ⫺358.19 ⫺430.5 ⫺665.9 ⫺666.1 ⫺112.5 ⫺130.96

71.97 99.6 205.0 120.9 204.6 117.0 224.7

⫺207.5 274.1 268.6 ⫺111.6 ⫺184.01 ⫺190.71 ⫺1210.56 ⫺1209.76 ⫺1248.00 ⫺2102.6 ⫺50.6 ⫺67.2 ⫺607.0

231.8 112.6 221.3 236.4 151.08 259.8 151.96 203.8 188.0 193.3 326.0 97.5 176.1 253.1

⫺835.38

245.2

⫺1256.9 ⫺2236.8

117 335

⫺774.9 ⫺72.8 13.4 ⫺531.6 ⫺599.8 ⫺2365.3 ⫺645.0 ⫺901.70 ⫺903.37

232.6 212.1 257.7 262.8 280.7 280.24 197.5 220.1 246.9

⫺1273.6 ⫺888.3

471.1 140.6

65.27 ⫺26.8 ⫺7.9

81.8 ⫺62.3

⫺17.6 139.3 ⫺6.7 142.26

⫺3.8

237.7

39.7

228.11 187.49 ⫺133.1

129.33

short standard long

DEAN #37261

LEFT

(McGHP)

6.84

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Antimony Sb SbBr3 SbCl3 SbCl5 SbF3 SbH3 SbI3 Sb2O3 Sb2O5 Sb2S3 Sb2Te3 Argon Ar Arsenic As gray AsBr3 AsCl3 AsF3 AsH3 AsI3 AsO⫺2 AsO34⫺ As2O5 As4O6 octahedral As2S3 Astatine At Barium Ba Ba2⫹ std. state Ba(OAc)2 acetate std. state BaBr2 std. state BaBr2 · 2H2O Ba(BrO3)2 BaC2O4 oxalate BaCl2 BaCl2 · 2H2O Ba(ClO3)2 Ba(ClO3)2 · H2O BaCO3 witherite BaCrO4 BaF2 std. state Ba(HCO3)2 std. state

Physical State

c g c g c lq c g c c c c c g c g lq g lq g g c aq aq c c c c c aq c aq c aq c c c c c c c c c c aq aq

⌬fH⬚ kJ · mol⫺1

0 262.3 ⫺259.4 ⫺194.6 ⫺382.0 ⫺440.16 ⫺915.5 145.11 ⫺100.4 ⫺708.8 ⫺971.9 ⫺174.9 ⫺56.5 0 0 ⫺130.0 ⫺305.0 ⫺261.5 ⫺821.3 ⫺785.8 66.44 ⫺58.2 ⫺429.0 ⫺888.1 ⫺924.87 ⫺1313.94 ⫺169.0 0 0 ⫺537.64 ⫺1484.5 ⫺1509.67 ⫺757.3 ⫺780.73 ⫺1366.1 ⫺752.66 ⫺1368.6 ⫺855.0 ⫺1456.9 ⫺762.7 ⫺1691.6 ⫺1213.0 ⫺1446.0 ⫺1207.1 ⫺1202.90 ⫺1921.63

⌬fG⬚ kJ · mol⫺1

0 222.1 ⫺239.3 ⫺223.9 ⫺323.7 ⫺350.2 147.74

⫺829.2 ⫺55.2 0 0 ⫺159.0 ⫺259.4 ⫺248.9 ⫺774.2 ⫺770.8 68.91 ⫺59.4 ⫺350.0 ⫺648.4 ⫺782.3 ⫺1152.52 ⫺168.6 0 0 ⫺560.74

S⬚ J · deg⫺1 · mol⫺1

45.7 180.3 207.1 372.9 184.1 301 232.8 215.5 123.01 125.1 182.0 234 154.846(3) 35.1 363.9 216.3 327.06 181.2 289.1 222.8 213.05 40.6 ⫺162.8 105.4 214.2 163.6

C⬚p J · deg⫺1 · mol⫺1

25.2 20.8 80.2 107.9

41.05 97.57 101.25 117.61 117.74

20.79 24.64 79.16 133.5 75.73 126.2 65.6 38.07 105.77

116.5 191.29 116.3

121.3 62.48 9.6

⫺1299.55 ⫺736.8 ⫺768.68 ⫺1230.5 ⫺577.4

182.8 146.0 174.5 226 243

⫺806.7 ⫺1293.2

123.67 202.9

⫺1270.7 ⫺1134.4 ⫺1345.3 ⫺1156.8 ⫺1118.38 ⫺1734.4

cap height base of text

393 112.1 158.6 96.4 ⫺17.0 192.1

28.10

77.0

75.14 161.96

86.0 71.20

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.85

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Ba(H2PO2)2 BaI2 std. state Ba(IO3)2 std. state BaMnO4 BaMoO4 Ba(NO2)2 Ba(NO3)2 std. state BaO BaO2 Ba(OH)2 Ba(OH)2 · H2O BaS BaSe BaSeO3 BaSiF6 BaSO3 BaSO4 BaTiO3 Beryllium Be Be2⫹ std. state BeAl2O4 chrysoberyl BeBr2 Be2C BeCl2 ␤ form BeCO3 BeF2 ␣ form BeI2 Be3N2 cubic BeO ␣ form BeO22⫺ 3BeO · B2O3 Be(OH)2 ␤ form BeS BeSeO4 std. state Be2SiO4 BeSO4 std. state BeSO4 · H2O BeWO4 Bismuth Bi BiBr3 BiCl3 BiH3

Physical State

⌬fH⬚ kJ · mol⫺1

c c aq c aq c c c c aq c c c c c c c c c c c

⫺1762.3 ⫺602.1 ⫺648.02 ⫺1027.2 ⫺980.3 ⫺1548 ⫺1507.5 ⫺768.2 ⫺988.0 ⫺952.36 ⫺548.0 ⫺634.3 ⫺944.7 ⫺3342.2 ⫺460.0 ⫺372 ⫺1040.6 ⫺1952.2 ⫺1179.5 ⫺1473.19 ⫺1659.8

c g aq c c c c c c c c c aq c c c c aq c c aq c c

0 324.(5) ⫺382.8 ⫺2301.0 ⫺353.5 91 ⫺490.4 1025.0 ⫺1026.8 ⫺192.5 ⫺588.3 ⫺609.4(25) ⫺790.8 ⫺3105 ⫺902.5 ⫺234.3 ⫺1205.2 ⫺982.0 ⫺2117 ⫺1200.8 ⫺1290.0 ⫺2423.75 ⫺1513

c g c c g

0 207.1 264 ⫺379.1 277.8

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

165.1 232.2 249.4 246.4 138 144.3

⫺792.6 ⫺783.41 ⫺520.4

213.8 302.5 72.07

151.38

⫺859.5 ⫺2793.2 ⫺456.0

107 427 78.2

101.6

⫺968.2 ⫺2794.1

167 163

⫺1362.2 ⫺1572.4

132.2 108.0

⫺379.7 ⫺2178.5 ⫺337 ⫺88 ⫺445.6 ⫺979.4 ⫺187 ⫺532.9 ⫺580.1 ⫺640.1 ⫺2939 ⫺815.0 ⫺233.0 ⫺1093.8 ⫺820.9 ⫺2003 ⫺1089.4 ⫺1124.3 ⫺2080.66 ⫺1405 0 168.2 234 ⫺315.1

9.50(8) 136.275(3) ⫺129.7 66.29 108.0 16.3 75.81 52.0 53.35 121.0 34.13 13.77(4) ⫺159.0 100 45.5 34.0 77.9 ⫺75.7 64.19 77.97 ⫺109.6 232.97 88.4 56.7 187.0 226 177.0

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

⫺601.4 ⫺663.92 ⫺864.8 ⫺816.7 ⫺1439.7 ⫺1439.7

0

top of rh base of rh

77.49 187.4 140.6 114.7

47.28

49.37

101.75 102.47 16.38

105.38 69.4 43.2 62.43 65.0 51.82 71.1 64.36 25.56 139.7 62.1 34.0 85.7 95.6 85.70 216.61 97.3 25.5 20.8 109 105.0

short standard long

DEAN #37261

LEFT

(McGHP)

6.86

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance BiI3 Bi2O3 BiOCl Bi2S3 Bi2(SO4)3 Bi2Te3 Boron B BBr3 B4C BCl3 BF3 BF⫺4 std. state BH3 BH⫺4 std. state B2H6 diborane(6) B5H9 pentaborane(9) B10H14 decaborane(14) BN B3N3H6 borazine BO2⫺ std. state B2O3 B(OH)⫺4 std. state B3O3H3 boroxin B2S3 Bromine Br atomic Br⫺ std. state Br2 Br⫺3 std. state BrCl BrF BrF3 BrF5 BrO⫺ std. state BrO⫺3 std. state BrO4⫺ Cadmium Cd Cd2⫹ CdBr2 std. state CdCl2 std. state CdCl2 · 5/2H2O

Physical State

⌬fH⬚ kJ · mol⫺1

c c c c c c

⫺100.4 ⫺574.0 ⫺366.9 ⫺143.1 ⫺2544.3 ⫺78.24

c g lq c g g aq g aq g lq c c lq g aq c aq c c

0 565.(5) ⫺239.7 ⫺62.7 ⫺403.8 ⫺1136.0(8) ⫺1574.9 100.0 48.16 35.6 42.7 ⫺29.83 ⫺254.4 ⫺541.0 ⫺510 ⫺772.37 ⫺1273.5(14) ⫺1344.03 ⫺1262 ⫺240.6

g aq lq g aq g g lq g lq g aq aq aq

111.87(12) ⫺121.41(15) 0 30.91(11) ⫺130.42 14.6 ⫺93.8 ⫺300.8 ⫺255.6 ⫺458.6 ⫺428.9 ⫺94.1 ⫺67.07 13.0

c g aq c aq c aq c

0 111.80(20) ⫺75.92(60) ⫺316.18 ⫺318.99 ⫺391.6 ⫺410.20 ⫺1131.94

⌬fG⬚ kJ · mol⫺1 ⫺175.3 ⫺493.7 ⫺322.2 ⫺140.6

0 ⫺238.5 ⫺62.1 ⫺388.7 ⫺1119.4 ⫺1487.0 111 114.27 86.7 171.8 212.9 ⫺228.4 ⫺392.7 ⫺389 ⫺678.94 ⫺1194.3 ⫺1153.32 ⫺11.56

82.4 ⫺103.97 0 ⫺107.07 ⫺0.96 ⫺109.2 ⫺240.5 229.4 ⫺351.9 ⫺351.6 ⫺33.5 18.6 118.1 0

⫺296.31 ⫺285.52 ⫺343.9 ⫺340.12 ⫺944.08

S⬚ J · deg⫺1 · mol⫺1

C⬚p J · deg⫺1 · mol⫺1

151.5 120.5 200.4

113.5

260.91

152.21

5.90(8) 153.436(15) 229.7 27.18 290.1 254.42(20) 179.9 187.9 110.5 232.1 184.2 234.9 14.80 199.6 288.61 ⫺37.24 53.97(30) 102.5 167 100.0 175.018(4) 82.55(20) 152.21(30) 245.468(5) 215.5 239.91 229.0 178.2 292.5 225.1 323.2 42.0 161.71 199.6 51.80(15) 167.749(4) ⫺72.8(15) 137.2 91.6 115.3 39.8 227.2

cap height base of text

122.2

11.1 128.03 53.76 62.7 50.45 36.22 56.9 151.13 221.2 19.72 96.94 62.8 98.3 111.7 20.8 ⫺141.8 75.67

34.98 32.97 124.6 66.6 99.6

25.9 20.8 76.7 74.7

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.87

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Cd(CN)2 std. state CdCO3 Cd(OAc)2 std. state CdF2 std. state CdI2 std. state CdI⫺4 std. state Cd(NH3)42⫹ std. state Cd(NO3)2 std. state CdO Cd(OH)2 CdS CdSO4 std. state CdSO4 · 8/3H2O CdSeO4 std. state CdTe Calcium Ca Ca2⫹ std. state Ca(OAc)2 std. state Ca3(AsO4)2 Ca(BO2)2 CaB4O7 CaBr2 std. state CaC2 CaCl2 std. state CaCl2 · 2H2O CaCN2 cyanamide Ca(CN)2 CaCO3 calcite aragonite CaC2O4 CaC2O4 · H2O CaCrO4 CaF2 Ca(formate)2 CaH2 CaHPO4 · 2H2O Ca(H2PO2)2 hypophosphite Ca(H2PO4)2 std. state

Physical State

⌬fH⬚ kJ · mol⫺1

c aq c aq c aq c aq aq aq c aq c c c c aq c c aq c

162.3 225.5 ⫺750.6 ⫺1047.9 ⫺700.4 ⫺741.15 ⫺203.3 ⫺186.3 ⫺341.8 ⫺450.2 ⫺456.3 ⫺490.6 ⫺258.35(40) ⫺560.7 ⫺161.9 ⫺933.4 ⫺985.2 ⫺1729.30(80) ⫺633.0 ⫺674.9 ⫺92.5

c g aq c aq c c c c aq c c aq c c c c c aq c c c c aq c c c c aq

0 177.8(8) ⫺543.0(10) ⫺1479.5 ⫺1514.73 ⫺3298.7 ⫺2030.9 ⫺3360.3 ⫺682.8 ⫺785.9 ⫺59.8 ⫺795.4 ⫺877.13 ⫺1402.9 ⫺350.6 ⫺184.5 ⫺1207.6 ⫺1207.8 ⫺1220.0 ⫺1360.6 ⫺1674.9 ⫺1379.1 ⫺1228.0 ⫺1208.1 1386.6 ⫺181.5 ⫺2403.58 ⫺1752.7 ⫺3135.41

⌬fG⬚ kJ · mol⫺1

267.4 ⫺669.4 ⫺816.4 ⫺647.7 ⫺635.21 ⫺201.4 ⫺180.8 ⫺315.9 ⫺226.4 ⫺300.2 ⫺228.7 ⫺473.6 ⫺156.5 ⫺822.7 ⫺822.2 ⫺1465.3 ⫺531.8 ⫺518.8 ⫺92.0 0 ⫺553.54 ⫺1292.35 ⫺3063.1 ⫺1924.1 ⫺3167.1 ⫺663.6 ⫺761.5 ⫺64.9 ⫺748.8 ⫺816.05

S⬚ J · deg⫺1 · mol⫺1

115.1 92.5 100 77.4 ⫺100.8 161.1 149.4 326 336.4 219.7 54.8(15) 96.0 64.9 123.0 ⫺53.1 229.65(40) 164.4 ⫺19.3 100.0 41.59(40) 154.887(4) ⫺56.2(10) 120.1 226 104.85 134.7 130.0 111.7 69.96 108.4 59.8

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1

80.0

43.4 55.5 99.6 213.3

25.9

103.98 157.9 75.04 62.72 72.9 738

⫺1129.1 ⫺1128.2 ⫺1081.4

91.7 88.0 ⫺110.0

83.5 82.3

⫺1514.0 ⫺1277.4 ⫺1175.6 ⫺1111.2

156.5 134 68.6 ⫺80.8

152.8

⫺142.5 ⫺2154.75

41.4 189.45

⫺2814.33

127.6

67.0

41.0 197.07

short standard long

DEAN #37261

LEFT

(McGHP)

6.88

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Ca(H2PO4)2 · H2O CaI2 std. state Ca(IO3)2 Ca[Mg(CO3)2] dolomite CaMoO4 Ca3N2 Ca(NO2)2 Ca(NO3)2 std. state CaO Ca(OH)2 Ca3P2 Ca3(PO4)2 Ca2P2O7 Ca10(PO4)6F2 fluoroapatite CaS CaSe CaSiO3 Ca2SiO4 3CaO · SiO2 CaSO3 · 2H2O CaSO4 CaSO4 · 1⁄2H2O CaSO4 · 2H2O Ca(VO3)2 CaWO4 Carbon C graphite diamond CN⫺ (CN)2 cyanogen CNBr CNCl CNF CNI CNN3 cyanogen azide OCN⫺ CO CO2 undissoc; std. state CO23⫺ C3O2 suboxide COBr2 COCl2 phosgene COClF COF2

Physical State

⌬fH⬚ kJ · mol⫺1

⌬fG⬚ kJ · mol⫺1

c c aq c c c c c c aq c c c c c c

⫺3409.67 ⫺533.5 ⫺653.2 ⫺1002.5 ⫺2326.3 ⫺1541.4 ⫺439.3 ⫺741.4 ⫺938.2 ⫺957.55 ⫺634.92(90) ⫺985.2 ⫺506 ⫺4120.8 ⫺3338.8 ⫺13,744

⫺3058.42 ⫺528.9 ⫺656.7 ⫺839.3 ⫺2163.6 ⫺1434.7

c c c c c c c aq c c c c c g c aq g g g g c g c aq g g aq aq g g g g g

⫺482.4 ⫺368.2 ⫺1634.9 ⫺2307.5 ⫺2929.2 ⫺1752.7 ⫺1425.2 ⫺1451.1 ⫺1576.7 ⫺2022.6 ⫺2329.3 ⫺1645.15 0 716.68(45) 1.897 150.6 306.7 186.2 137.95

⫺742.8 ⫺776.22 ⫺603.3 ⫺897.5 ⫺3884.8 ⫺3132.1 ⫺12,983 ⫺477.4 ⫺363.2 ⫺1549.7 ⫺2192.8 ⫺2784.0 ⫺1555.2 ⫺1309.1 ⫺1298.1 ⫺1436.8 ⫺1797.5 ⫺2169.7 ⫺1538.50 0 2.900 172.4 297.2 165.3 131.02

166.2 225.5 387.4 ⫺146.0 ⫺110.53(17) ⫺393.51(13) ⫺413.26(20) ⫺675.23(25) ⫺93.7 ⫺96.2 ⫺219.1

185.0 196.6 ⫺97.4 ⫺137.16 394.39 ⫺386.0 ⫺527.9 ⫺109.8 ⫺110.9 ⫺204.9

⫺639.8

⫺623.33

S⬚ J · deg⫺1 · mol⫺1

C⬚p J · deg⫺1 · mol⫺1

259.8 142.0 169.5 230 155.18 122.6 105.0

258.82 77.16

193.3 239.7 38.1(4) 83.4

149.37

236.0 189.24 775.7

227.8 187.8 751.9

56.5 67 81.92 127.7 168.6 184 108.4 ⫺33.1 130.5 194.1 179.1 126.40

47.4

5.74(10) 158.100(3) 2.377 94.1 241.9 248.36 236.2 224.7 96.2 256.8 106.7 197.660(4) 213.785(10) 119.36(60) ⫺50.0(10) 276.4 309.1 283.50 276.7 258.89

cap height base of text

157.53 114.3 113.0

42.0 87.5

85.27 128.8 171.9 178.7 99.0 119.4 186.0 166.8 114.14 8.517 6.116 56.9 46.9 45.0 41.8 48.3

29.14 37.13

67.0 61.8 57.70 52.4 46.8

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.89

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance COS carbonyl sulfide CS2 CTe2 Cerium Ce ␥, fcc Ce3⫹ std. state Ce4⫹ std. state CeCl3 std. state CeF3 CeI3 Ce(NO3)3 CeO2 Ce2O3 CeS Ce2(SO4)3 std. state Ce2(SO4)3 · 8H2O Cesium Cs

Cs⫹ std. state Cs acetate CsBO2 CsBr std. state CsCl std. state CsClO4 Cs2CO3 std. state CsF std. state Cs formate CsHCO3 CsHF CsHSO4 CsI std. state CsIO3 CsNO3 std. state Cs2O CsOH std. state Cs2PtCl6 std. state Cs2S Cs2Se

Physical State

⌬fH⬚ kJ · mol⫺1

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

g lq g lq

⫺142.0 89.0 117.7 164.8

⫺166.9 67.1

237.8

c aq aq c aq c c c c c c c aq c

0 ⫺696.2 ⫺537.2 ⫺1060.5 ⫺1197.5 ⫺1635.9 ⫺669.3 ⫺1225.9 ⫺1088.7 ⫺1796.2 ⫺459.4 ⫺3954.3 ⫺4176.9 ⫺5522.9

0 ⫺672.0 ⫺503.8 ⫺984.8 ⫺1065.7 ⫺1556 ⫺674

72.0 ⫺205.0 ⫺301.0 151.0 ⫺38.0 115.1 209

c lq g aq aq c c aq c aq c c aq c aq aq c c c aq c aq c c aq c c aq aq aq aq

0 2.087 76.5(10) ⫺258.00(50) ⫺744.3 ⫺972.0 ⫺405.8 ⫺379.8 ⫺442.8 ⫺425.4 ⫺443.1 ⫺1139.7 ⫺1193.7 ⫺553.5 ⫺590.9 ⫺683.8 ⫺966.1 ⫺923.8 ⫺1158.1 ⫺1145.6 ⫺346.6 ⫺313.5 ⫺525.9 ⫺506.0 ⫺465.6 ⫺345.8 ⫺417.2 ⫺488.3 ⫺1184.9 ⫺483.7

⫺1024.7 ⫺1706.2 ⫺451.5 ⫺3652.6 ⫺5607.4 0 0.025 ⫺292.0 ⫺661.3 ⫺915.0 ⫺391.4 ⫺396.0 414.4 ⫺423.3 ⫺314.3 ⫺1054.4 ⫺1111.9 ⫺525.5 ⫺570.8 ⫺643.0

231.56

62.30 150.6 78.2

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1 41.50 74.6 45.4

26.9

87.4 99.3

61.63 114.6 50.0

⫺318

85.23(40) 92.1 175.601(3) 132.1(5) 219.7 104.4 113.05 215.5 101.18 189.4 175.1 204.5 209.2 92.8 119.2 226.0

⫺858.9

135.2

⫺1047.9 ⫺340.6 ⫺343.6 ⫺433.9 ⫺406.6 ⫺403.3 ⫺308.2 370.7 ⫺449.3 ⫺1066.9 ⫺498.3 454.8

264.8 123.1 244.4 155.2 279.5 146.9 98.7 122.3 485.8 251.0

32.20 32.4 ⫺10.5 80.6 52.93 52.44 ⫺146.9 108.3 123.9 51.1

87.3

52.8 ⫺152.7 167 ⫺99.2 76.0 67.9

short standard long

DEAN #37261

LEFT

(McGHP)

6.90

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Cs2SO4 std. state Chlorine Cl atomic Cl⫺ std. state Cl2 ClF ClF3 ClF5 ClO ClO⫺ std. state ClO2 ClO⫺2 std. state ClO⫺3 std. state ClO3F perchloryl fluoride ClO⫺4 std. state Cl2O Cl2O7 Chromium Cr Cr2⫹ std. state CrBr2 CrCl2 CrCl3 Cr(CO)6 hexacarbonyl CrF2 CrF3 Cr2FeO4 CrI2 CrI3 CrN CrO2 Cr2O3 Cr3O4 CrO2Cl2 CrO24⫺ std. state HCrO⫺4 std. state Cr2O72⫺ std. state Cr2(SO4)3 Cobalt Co Co2⫹ std. state Co3⫹ std. state CoBr2 std. state CoCl2 std. state CoCO3 CoF2 CoF3

Physical State c aq g aq g g g g g aq g aq aq g aq g lq g

⌬fH⬚ kJ · mol⫺1 ⫺1443.0 ⫺1425.8 121.301(8) ⫺167.08(10) 0 ⫺50.3 ⫺163.2 ⫺239 101.8 ⫺107.1 102.5 ⫺66.5 ⫺104.0 ⫺23.8 ⫺128.10(40) 80.3 238.1 1138

c aq c c c c c c c c c c c c c g aq aq aq c

0 ⫺143.5 ⫺302.1 ⫺395.4 ⫺556.5 ⫺1077.8 ⫺778.0 ⫺1159 ⫺1444.7 ⫺156.9 ⫺205.0 ⫺117 ⫺598.0 ⫺1140 ⫺1131.0 ⫺538.1 ⫺881.15 ⫺878.22 ⫺1490.3 ⫺609.6

c aq aq c aq c aq c c c

0 ⫺58.2 92 ⫺220.9 ⫺301.3 ⫺312.5 ⫺392.5 ⫺713.0 ⫺692 ⫺790

⌬fG⬚ kJ · mol⫺1 ⫺1323.6 ⫺1328.6

⫺131.3 0 ⫺51.84 ⫺123.0 ⫺147 98.1 ⫺36.8 120.5 17.2 ⫺8.0 48.2 ⫺8.62 97.9

0

S⬚ J · deg⫺1 · mol⫺1 211.9 286.2 165.190(4) 56.60(20) 233.08(10) 217.9 281.6 310.74 226.6 41.8 256.8 101.3 162.3 279.0 184.0(15) 266.2

C⬚p J · deg⫺1 · mol⫺1 134.9

⫺136.4 33.95 32.08 63.85 97.17 31.5 42.00

64.9 45.4

23.8

23.43

⫺356.0 ⫺486.1

115.3 123.0 293.01

71.2 91.8 226.23

⫺1088 ⫺1343.8

93.9 146.0

78.7 133.6

38

52.7

⫺93

cap height base of text

⫺1058.1

81.2

118.7

⫺501.6 ⫺727.85 ⫺764.84 ⫺1301.2

329.8 50.21 184.1 261.9 269.9

84.5

302.6

0 ⫺54.4 134

30.0 ⫺113 ⫺305

24.8

⫺262.3 ⫺269.8 ⫺316.7

50 109.2 0

78.49

82.4 95

68.9 92

79.5

⫺647 ⫺719

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.91

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance CoI2 Co(NH3)62⫹ std. state Co(NH3)63⫹ std. state Co(NO3)2 std. state CoO Co3O4 Co(OH)2 CoS Co2S3 CoSO4 std. state CoSO4 · 7H2O Copper Cu Cu⫹ std. state Cu2⫹ std. state Cu(OAc)2 acetate std. state Cu3(AsO4)2 std. state CuBr CuBr2 CuCl CuCl2 Cu(ClO4)2 std. state CuCN CuCNS std. state Cu(CNS)2 std. state CuF CuF2 Cu(formate)2 CuI Cu(NH3)42⫹ std. state Cu(NO3)2 std. state CuO Cu2O Cu(OH)2 CuS Cu2S CuSe Cu2Se CuSO4 std. state CuSO4 · 5H2O CuWO4 Dysprosium Dy Dy3⫹ std. state

Physical State

⌬fH⬚ kJ · mol⫺1 ⫺88.7 ⫺168.6 ⫺584.9

c aq aq aq c aq c c c c c c aq c

⫺420.5 ⫺472.8 ⫺237.7 ⫺891 ⫺539.7 ⫺82.8 ⫺147.3 ⫺888.3 ⫺967.3 ⫺2979.93

c g aq aq c aq aq c c c c aq c aq aq c c aq c aq c aq c c c c c c c c aq c c

0 337.4(12) 71.67 64.9(10) ⫺893.3 ⫺907.25 ⫺1581.97 ⫺104.6 ⫺141.84 ⫺137.2 ⫺220.1 ⫺193.89 95.0 138.11 217.65 ⫺280 ⫺542.7 ⫺786.34 67.8 ⫺348.5 ⫺302.9 ⫺349.95 ⫺157.3 ⫺168.6 ⫺450 ⫺53.1 ⫺79.5 ⫺39.5 ⫺59.4 ⫺771.4(12) ⫺844.50 ⫺2279.65 ⫺1105.0

c aq

0 ⫺699.0

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺157.7 ⫺157.3 ⫺189.5

109.0 146

⫺277.0 ⫺214.0 ⫺774 ⫺454.4

180 53.0 102.5 79.0

⫺782.4 ⫺799.1 ⫺2473.83

118.0 ⫺92.0 406.06

0 50.00 65.52 ⫺673.29 ⫺1100.48 ⫺100.8

33.15(8) 166.398(4) 40.6 ⫺98.(4) 73.6 ⫺804.2 96.2

⫺119.9 ⫺175.7 48.28 108.4 142.67 250.87 ⫺260 ⫺492 ⫺636.4 ⫺69.5 ⫺111.3

86.2 108.09 264.4 90.00 184.93 189.1 64.9 77.45 84 96.7 273.6

⫺157.15 ⫺129.7 ⫺149.0 ⫺373 ⫺53.7 ⫺86.2

193.3 42.6 93.1 108.4 66.5 120.9

⫺662.2 ⫺679.11 ⫺1880.04

0 ⫺665.0

157.3 109.2(4) ⫺79.5 300.4

75.6 ⫺231.0

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1

55.3 123.4

103 390.49 24.44

54.7 48.5 71.88 61.04

51.9 65.55 54.1

42.2 63.6 95.19 47.8 76.3 88.70 98.87 280

27.7 21.0

short standard long

DEAN #37261

LEFT

(McGHP)

6.92

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance DyCl3 DyF3 Dy2O3 Erbium Er Er3⫹ std. state ErCl3 Er2O3 Europium Eu Eu2⫹ std. state Eu3⫹ EuCl2 EuCl3 EuF3 Eu2O3 monoclinic Eu3O4 Eu(OH)3 Fluorine F atomic F⫺ F2 FNO3 FO F2O F2O2 Francium Fr FrCl Fr2O Gadolinium Gd Gd3⫹ std. state GdCl3 std. state GdF3 Gd2O3 monoclinic Gallium Ga

Ga3⫹ GaAs GaBr3 GaCl3 GaF3 GaI3 Ga2O3 rhombic

Physical State

⌬fH⬚ kJ · mol⫺1

c aq c c

⫺1000 ⫺1197.0 ⫺1711.0 ⫺1863.1

c aq c aq c

0 ⫺705.4 ⫺998.7 ⫺1207.1 ⫺1897.9

c aq aq aq c aq c c c c

0 ⫺527.0 ⫺605.0 ⫺862.0 ⫺936.0 ⫺1106.2 ⫺1571 ⫺1651.4 ⫺2272.0 ⫺1332

g aq g g g g g

79.38(30) ⫺335.35(65) 0 10.5 109.0 24.7 18.0

c c c

0 ⫺439 ⫺338

c aq c aq lq c

0 ⫺686.0 ⫺1008.0 ⫺1188.0 ⫺1297 ⫺1819.6

c lq g aq c c c c c c

0 5.6 272.0 ⫺211.7 ⫺71.0 ⫺386.6 ⫺524.7 ⫺1163.0 ⫺238.9 ⫺1089.1

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺1059.0

⫺61.9

⫺1771.5

149.8

0 ⫺669.1

73.18 ⫺244.3

⫺1062.7 ⫺1808.7

⫺75.3 155.6

0 540.2 ⫺574.0

77.78 ⫺8.0 ⫺222.0

⫺856 ⫺967.7

144.1 ⫺54.0

⫺1556.9 ⫺2142.0 ⫺1195

146 205.0 119.9

62.3 ⫺278.8 0 73.7 105.0 41.9

0

158.751(4) ⫺13.8(8) 202.791(5) 292.9 216.8 247.4

C⬚p J · deg⫺1 · mol⫺1 100.0 ⫺389.0 116.27 28.12 21.0 100.0 ⫺389.0 108.49 27.66 8.0

⫺402.0 122.2

22.7 ⫺106.7 31.30 65.22 30.5 43.3

31.80 53.56

299.2

95.40 113.0 156.9

0 ⫺661.0 ⫺933 ⫺1059.0

68.07 ⫺205.9 151.4 ⫺36.8

37.03

⫺1730

150.6

0

40.8

233.7 ⫺159.0 ⫺67.8 ⫺359.8 ⫺454.8 ⫺1085.3 ⫺998.3

169.0 ⫺331.0 64.2 180.0 142.0 84 205.0 84.98

cap height base of text

88.0 ⫺410.0 106.7 26.06 25.3 46.2

100 92.1

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.93

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Ga(OH)3 GaSb Germanium Ge GeBr4 GeCl4 GeF4 GeH4 GeI4 GeO2 tetragonal GeP GeS Gold Au AuBr AuBr3 AuCl AuCl3 AuCl⫺4 std. state Au(CN)⫺2 std. state AuF3 AuSb2 AuSn Hafnium Hf hexagonal HfC HfCl4 HfF4 monoclinic HfO2 Helium He Holmium Ho Ho3⫹ std. state HoCl3 std. state HoF3 Ho2O3 Hydrogen H atomic H⫹ std. state H2 H2H 2 H2 (D2) deuterium HAsO⫺2 undissoc; std. state

Physical State c c c g lq g lq g g g c g c c c c c c c c aq aq c c c c c c c c g c aq c aq c c g aq g g g aq

⌬fH⬚ kJ · mol⫺1 ⫺964.4 ⫺41.8 0 372.0(30) ⫺347.7 ⫺300.0 ⫺531.8 ⫺495.8 ⫺1190.20(50) 90.8 ⫺141.8 ⫺56.9 ⫺580.0(10) ⫺21.0 ⫺69.0 0 ⫺14.0 ⫺53.3 ⫺34.7 ⫺117.6 ⫺322.2 242.3 ⫺363.6 ⫺19.46 ⫺30.5 0 ⫺230.1 ⫺990.4 ⫺1930.5 ⫺1144.7 0 0 ⫺705.0 ⫺1005.4 ⫺1206.7 ⫺1707.0 ⫺1880.7 217.998(6) 0 0 0.321 0 ⫺456.5

⌬fG⬚ kJ · mol⫺1 ⫺831.3 ⫺38.9 0 331.2 ⫺331.4 ⫺318.0 ⫺462.8 ⫺457.3 ⫺1150.0 113.4 ⫺144.4 ⫺106.3 ⫺521.4 ⫺17.0 ⫺71.6 0

⫺237.32 285.8

0 ⫺901.3 ⫺1830.5 ⫺1088.2 0

S⬚ J · deg⫺1 · mol⫺1 100.0 76.07 31.09(15) 167.904(5) 280.8 396.2 245.6 347.7 301.9(10) 217.02 271.1 428.9 39.71(15) 63.0 71

48.53 23.3 30.7 101.8 96.1 81.84 45.02 104.1 52.1

25.36

92.9 148.1 266.9 172 114.2 119.2 93.7

48.74 94.81

43.56 41.21 190.8 113 59.3

25.69 34.43 120.46

91.29 77.40 49.41

60.25 20.786

0 ⫺673.7

75.3 226.8

⫺1067.3

⫺57.7

27.15 17.0 88 ⫺393.0

⫺1791.2

158.2

115.0

203.3 0 0 ⫺1.463 0 ⫺402.71

114.717(2) 0 130.680(3) 143.80 144.96 125.9

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

47.4

126.153(2)

top of rh base of rh

20.8 0 28.84 29.20 29.19

short standard long

DEAN #37261

LEFT

(McGHP)

6.94

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance H2AsO⫺3 undissoc; std. state H3AsO3 undissoc; std. state HAsO24⫺ undissoc; std. state H2AsO⫺4 undissoc; std. state H3AsO3 undissoc; std. state HBO2 H3BO3 undissoc HBr std. state HBrO undissoc; std. state HBrO3 std. state HCl std. state 2 HCl deuterium chloride HClO undissoc; std. state HClO2 undissoc; std. state HClO3 std. state HClO4 std. state HClO4 · H2O HClO4 · 2H2O HCN ionized; std. state undissoc; std. state HCNO ionized; std. state undissoc; std. state HCNS ionized; std. state HCOO⫺ formate CH3COO⫺ acetate HCO⫺3 std. state H2CO3 std. state HC2O⫺4 H2C2O4 C2O24⫺ H2CS3 trithiocarbonic acid HF undissoc; std. state F⫺ 2 HF HF⫺2 std. state H2F2 dimer H2Fe(CN) 26⫺ std. state

Physical State

⌬fH⬚ kJ · mol⫺1

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

aq

⫺714.79

⫺587.22

110.5

aq

⫺742.2

⫺639.90

195.0

aq aq

⫺906.34 ⫺909.56

⫺714.70 ⫺753.29

⫺1.7 117

⫺766.1 ⫺723.4 ⫺968.9

184 38 89.95(60) 162.4(6) 198.700(4) 82.4 142 161.71 186.902(5) 56.5 192.63 236.7 142 188.3 162.3

c aq c c aq g aq aq aq g aq g g aq aq aq lq aq c lq lq g aq aq aq aq aq aq aq aq aq aq c aq lq

⫺906.30 ⫺902.5 ⫺794.3 ⫺1094.8(8) ⫺1072.8(8) ⫺36.29(16) ⫺121.55 ⫺113.0 ⫺67.07 ⫺92.31(10) ⫺167.15 ⫺93.35 ⫺78.7 ⫺120.9 ⫺51.9 ⫺103.97 ⫺40.58 ⫺129.33 ⫺302.21 ⫺677.98 108.87 135.1 150.6 107.11 ⫺146.0 ⫺154.39 76.44 ⫺425.6 ⫺486.0 ⫺689.93(20) ⫺699.65 ⫺818.4 ⫺821.7 ⫺825.1 25.1

g lq aq aq g aq g aq

⫺273.30(70) ⫺299.78 ⫺320.08 ⫺332.63 ⫺275.5 ⫺649.94 ⫺572.66 455.6

⫺53.4 ⫺103.97 ⫺82.4 18.54 ⫺95.30 ⫺131.25 ⫺95.94 ⫺66.1 ⫺79.9 5.9 ⫺8.03 ⫺8.62

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

54.4 86.1 29.1 ⫺141.8

29.12 ⫺136.4 29.17 37.15

182.0

124.93 124.7 172.4 119.66 ⫺97.5 ⫺117.2 92.68 ⫺351.0 ⫺369.3 ⫺586.85 ⫺623.16 ⫺698.3 ⫺723.7 ⫺673.9 27.82

112.84 201.81 94.1 124.7 106.7 144.8 144.4 92.0 86.6 98.4(5) 187.4 149.4 109.8 45.6 233.0

⫺275.4 75.40 ⫺296.86 ⫺278.8 ⫺277.27 ⫺578.15 ⫺544.51 658.44

173.779(3) 51.67 88.7 ⫺13.8 179.70 92.5 238 218

70.63 35.86

⫺40.2 ⫺87.9 ⫺6.3

91.0 149.8 29.14

⫺106.7 29.14 44.89

short standard long

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(McGHP)

RIGHT

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6.95

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance HFO HI std. state HIO undissoc; std. state HIO3 H2MoO4 HN HN3 H2N 2 H2N2 cis-diazine HNCO isocyanic acid HNCS isothiocyanic acid HNO2 HNO3 std. state H2N2O2 hyponitrous acid HO hydroxyl HO⫺ HO2 HO⫺2 std. state H2O

1

H2HO H2O deuterium oxide H2O2 hydrogen peroxide 2

undissoc; std. state HOCN undissoc; std. state OCN⫺ cyanate std. state HPO3 HPO42⫺ std. state H2PO⫺4 std. state HPH2O2 hypophosphorous acid H3PO3 H3PO4 ionized; std. state undissoc; std. state HP2O73⫺ H2P272⫺ H4P2O7 undissoc; std. state HReO4 HS HS⫺ std. state H2S undissoc; std. state

Physical State

⌬fH⬚ kJ · mol⫺1

g g aq aq c c g lq g g g g g g lq g aq aq g aq g aq c lq g g g lq g aq aq aq c aq aq

98 26.50(10) ⫺55.19 ⫺138.1 ⫺230.1 ⫺1046.0 351.5 264.0 294.1 184.9 207 ⫺116.73 127.61 ⫺79.5 ⫺174.1 ⫺133.9 ⫺207.36 ⫺57.3 39.0 ⫺230.015 10.5 ⫺160.33 ⫺292.72 ⫺285.830(40) ⫺241.826(40) ⫺245.37 ⫺249.20 ⫺187.78 ⫺136.3 ⫺191.17 ⫺154.39 ⫺146.02 ⫺948.51 ⫺1299.0(15) ⫺1302.6(15)

c c c lq aq aq aq aq c aq c g aq g aq

⫺604.6 ⫺964.4 ⫺1284.4 ⫺1271.7 ⫺1277.4 ⫺1288.34 ⫺2274.8 ⫺2278.6 ⫺2241.0 ⫺2268.6 ⫺762.3 142.7 ⫺16.3(15) ⫺20.6(5) ⫺38.6(15)

⌬fG⬚ kJ · mol⫺1 ⫺86 1.7 ⫺51.59 ⫺99.2

345.6 327.2 328.1 194.6 241 ⫺107.36 112.88 ⫺46.0 ⫺80.7 ⫺73.54 ⫺111.34 36.0 34.2 ⫺157.28 22.6 67.4 ⫺237.14 ⫺228.61 ⫺233.18 ⫺234.54 ⫺120.42 ⫺105.6 ⫺134.10 ⫺117.2 ⫺97.5 ⫺1089.26 ⫺1130.39

S⬚ J · deg⫺1 · mol⫺1 226.8 206.590(4) 111.3 95.4

181.2 140.6 239.0 195.0 224.09 238.11 248.03 254.1 155.60 266.9 146.4 218 183.64 ⫺10.90 229.0 23.9 69.95(3) 188.835(10) 199.51 198.33 109.6 232.7 143.9 144.8 106.7

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1 35.93 29.16 ⫺142.3

29.2 43.7 33.9 39.02 44.85 46.40 45.5 109.9 54.1 ⫺86.6 30.00 ⫺148.5 34.9 37.11 75.35 33.60 33.79 34.25 89.1 43.14

⫺33.5(15) 92.5(15)

⫺1124.3 ⫺1123.6 ⫺1018.8 ⫺1142.65 ⫺1972.2 ⫺2010.2

110.5 150.8 222 158.2 46.0 163.0

⫺2032.2 ⫺656.4 113.3 12.05 ⫺33.4 ⫺27.87

268 158.2 195.7 67.(5) 205.81(5) 126.(5)

106.1 145.06

32.3 34.19

short standard long

DEAN #37261

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(McGHP)

6.96

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance 2H S 2 H2S2 HSbO2 undissoc; std. state HSCN undissoc; std. state SCN⫺ std. state HSe⫺ std. state H2Se HSeO⫺3 std. state H2SeO3 undissoc; std. state HSeO⫺4 std. state H2SeO4 H2SiO3 undissoc; std. state H4SiO4 undissoc; std. state HSO⫺3 std. state HSO⫺4 HSO3Cl HSO3F

H2SO3 undissoc; std. state H2SO4 std. state H2SO4 · H2O H2SO4 · 2H2O H2SO4 · 3H2O H2SO4 · 4H2O H2S2O7 H2Te H2WO4 Indium In In3⫹ InAs InBr3 InCl3 InF InH InI InI3 InOH2⫹ In(OH)⫹2 In2O3 InP InS In2S3 In2Se3 InSb Iodine I atomic

Physical State

⌬fH⬚ kJ · mol⫺1

g g aq aq aq aq g aq c aq aq c c aq c aq aq aq lq lq g aq lq aq lq lq lq lq c g c

⫺23.9 15.5 ⫺487.9 76.4 76.44 15.9 29.7 ⫺514.55 ⫺524.46 ⫺507.48 ⫺581.6 ⫺530.1 ⫺1188.67 ⫺1182.8 ⫺1481.1 ⫺1468.6 ⫺626.22 ⫺886.9(10) ⫺601.2 ⫺795.0 ⫺753 ⫺608.81 ⫺814.0 ⫺909.27 ⫺1127.6 ⫺1427.1 ⫺1720.4 ⫺2011.2 ⫺1273.6 99.6 ⫺1131.8

c aq c c c g g c c aq aq c c c c c c g

0 ⫺105.0 ⫺58.6 ⫺428.9 ⫺537.2 ⫺203.4 215.5 ⫺116.3 ⫺238.0 ⫺370.3 ⫺619.0 ⫺925.27 ⫺88.7 ⫺138.1 ⫺427 ⫺343 ⫺30.5 106.76(4)

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺35.3

215.3

⫺407.5 97.7 92.68 43.9 15.9 ⫺411.54

46.6 144.3 144.5 79.0 219.0 135.1

⫺426.22 ⫺452.3

207.9 149.4

C⬚p J · deg⫺1 · mol⫺1 35.76 51.5 ⫺40.2 ⫺40.2 34.7

⫺1092.4 ⫺1079.5 ⫺1333.0 ⫺1316.7 ⫺527.8 ⫺755.9

134.0 109 192 180 139.8 131.7(30)

⫺691 ⫺537.90 ⫺689.9 ⫺744.63 ⫺950.3 ⫺1199.6 ⫺1443.9 ⫺1685.8

297 232.2 156.90 20.1 211.5 276.4 345.4 414.5

138.9 293 214.3 261.5 319.1 386.4

⫺1003.9

228.9 145

35.56 113

0 ⫺98.0 ⫺53.6

57.8 ⫺151.0 75.7

26.7

190.3 ⫺120.5 ⫺313.0 ⫺525.0 ⫺830.73 ⫺77.0 ⫺131.8 ⫺412.5 ⫺25.5 70.2

207.53 130.0

⫺84.0

75.24

47.78

29.58

⫺88.0 25.0 104.2 59.8 67 163.6

118.0

86.2

49.5

180.787(4)

cap height base of text

92 45.44

20.8

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.97

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance I⫺ std. state I2 std. state I⫺3 std. state IBr ICl

ICl3 IF IF5 IF7 IO IO⫺ std. state IO⫺3 std. state IO⫺4 std. state I2O5 Iridium Ir IrCl3 IrF6 IrO2 IrS2 Iron Fe alpha Fe2⫹ std. state Fe3⫹ std. state FeBr2 std. state FeBr3 Fe3C ␣-cementite FeCl2 FeCl3 std. state Fe(CN)36⫺ std. state Fe(CN)46⫺ std. state FeCNS2⫹ std. state FeCO3 Fe(CO)5 FeCr2O4 FeF2 std. state FeF3 FeI2 std. state

Physical State

⌬fH⬚ kJ · mol⫺1

⌬fG⬚ kJ · mol⫺1

aq c g aq aq c g c lq g c g lq g g g aq aq aq c

⫺56.78(5) 0 62.42(8) 22.6 ⫺51.5 ⫺10.5 40.8 ⫺35.4 ⫺23.93 17.8 ⫺89.5 ⫺95.7 ⫺864.8 ⫺822.5 ⫺961.1 175.1 ⫺107.5 ⫺221.3 ⫺151.5 ⫺158.07

⫺51.59 0 19.37 16.40 ⫺51.5

c c c c c

0 ⫺245.6 ⫺579.65 ⫺274.1 ⫺138.0

c aq aq c aq c aq c c aq c aq aq aq aq c lq c c aq c aq c aq

0 ⫺89.1 ⫺48.5 ⫺249.8 ⫺332.2 ⫺286.2 ⫺413.4 25.1 ⫺341.8 ⫺423.4 ⫺399.4 ⫺550.2 561.9 455.6 23.4 ⫺740.6 ⫺774.0 ⫺1446.0 ⫺711.3 ⫺754.4 ⫺1042 ⫺1046.4 ⫺113.0 ⫺199.6

S⬚ J · deg⫺1 · mol⫺1 106.45(30) 116.14(30) 260.687(5) 137.2 239.3

⫺142.3 54.44 36.86

258.8 97.93 135.1 247.6 167.4 236.3

⫺751.5 ⫺835.8 149.8 ⫺38.5 ⫺128.0 ⫺58.6

327.7 347.7 245.5 ⫺5.4 118.4 222

0 180 ⫺461.66

35.48 113 247.7 57.3

25.06

27.32 ⫺137.7 ⫺315.9 140.7 27.2

25.09

⫺316.7 20.1 ⫺302.3 ⫺341.3 ⫺333.9 ⫺398.3 729.3 694.9 71.1 ⫺666.7 ⫺705.3 ⫺1343.9 ⫺668.6 ⫺636.5 ⫺972 ⫺840.9 ⫺111.7 ⫺182.1

⫺68.6 104.6 118.0 ⫺24.7 142.34 ⫺146.4 270.3 95.0 ⫺130 92.9 338.1 146.2 86.99 ⫺165.3 98 ⫺357.3 167.4 84.9

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

3.7 ⫺14.05 ⫺13.6 ⫺5.5 ⫺22.34 ⫺118.5

0 ⫺78.87 ⫺4.7 ⫺238.1 ⫺286.81

top of rh base of rh

36.4 55.23 35.6 33.4 99.2 134.5 32.9

57.32

80.2

105.9 76.7 96.65

82.1 240.6 133.8 68.12 91.0 83.7

short standard long

DEAN #37261

LEFT

(McGHP)

6.98

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance FeI3 FeMoO4 Fe2N Fe(NO3)3 std. state FeO Fe2O3 hematite Fe3O4 magnetite FeOH⫹ std. state Fe(OH)2⫹ std. state Fe(OH)2 Fe(OH)3 FeS FeS2 marcasite FeS2 pyrite FeSiO3 Fe2SiO4 FeSO4 std. state Fe2(SO4)3 std. state FeTiO3 FeWO4 Krypton Kr Lanthanum La La3⫹ LaCl3 std. state LaCl3 · 7H2O LaI3 La(NO3)3 std. state La2O3 La2(SO4)3 La2Te3 Lead Pb Pb2⫹ Pb(OAc)2 Pb(BO2)2 PbB4O7 PbBr2 Pb(CH3)4 Pb(C2H5)4 PbCl2 PbCl4 PbClF

Physical State aq c c aq c c c aq aq c c c c c c c c aq c aq c c g

⌬fH⬚ kJ · mol⫺1 ⫺214.2 ⫺1075.0 ⫺3.8 ⫺670.7 ⫺272.0 ⫺824.2 ⫺1118.4 ⫺324.7 ⫺290.8 ⫺574.0 ⫺833 ⫺100.0 ⫺167.4 ⫺178.2 ⫺1155 ⫺1479.9 ⫺928.4 ⫺998.3 ⫺2583.0 ⫺2825.0 ⫺1246.4 ⫺1155.0 0

c aq c aq c c c aq c c c

0 ⫺707.1 ⫺1072.2 ⫺1208.8 ⫺3178.6 ⫺668.9 ⫺1254.4 ⫺1329.3 ⫺1793.7 ⫺3941.3 ⫺724

c g aq c c c c aq lq lq c aq lq c

0 195.2(8) 0.92(25) ⫺964.4 ⫺1556 ⫺2858 ⫺278.7 ⫺244.8 97.9 52.7 ⫺359.4 ⫺336.0 ⫺329.3 ⫺534.7

⌬fG⬚ kJ · mol⫺1 ⫺159.4 ⫺975.0 ⫺338.5 ⫺251.4 ⫺742.2 ⫺1015.4 ⫺277.4 ⫺229.4 ⫺490.0 ⫺705 ⫺100.4 ⫺156.1 ⫺166.9 ⫺1379.0 ⫺820.8 ⫺823.4 ⫺2262.7 ⫺2243.0 ⫺1054.0 0 0 683.7 ⫺1077.4 ⫺2713.3

⫺1705.8 ⫺714.6 0 162.2 ⫺24.4

S⬚ J · deg⫺1 · mol⫺1 18.0 129.3 101.3 123.4 60.75 87.40 145.27 ⫺29 ⫺142 87.9 104.6 60.32 53.87 52.92 87.5 145.18 107.5 ⫺117.6 307.5 ⫺571.5 105.9 131.8 164.085(3) 56.9 ⫺217.6 144.4 ⫺50.0 462.8

127.32 280 231.63 64.80(30) 175.375(5) 18.5(10)

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

118.5 70.0 49.91 103.9 143.4

97.1 101.7 50.52 62.39 62.12 89.4 132.9 100.6 264.8 99.5 114.4 20.786 27.11 ⫺13.0 108.8 ⫺423.0 431.0

108.78 132.13 26.84 20.8

⫺1450 ⫺2667 ⫺261.9 ⫺232.3

131 167 161.5 175.3

107.1 168 80.1

⫺314.1 ⫺286.9

464.6 136 123.4

307.4 77.1

⫺488.3

121.8

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.99

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance PbCO3 PbC2O4 PbCrO4 PbF2 PbF4 PbI2 PbMoO4 Pb(N3)2 monoclinic Pb(NO3)2 PbO litharge PbO2 Pb3O4 Pb3(PO4)2 PbS PbSe PbSeO4 PbSiO3 PbSiO4 Pb2SiO4 PbSO3 PbSO4 PbSO4 · PbO PbTe Lithium Li Li⫹ std. state Li3AlF6 cryolite LiAlH4 LiAlO2 LiBeF3 LiBH4 LiBH4 · tetrahydrofuran Li2BeF4 LiBO2 Li2B4O7 LiBr std. state LiBrO3 std. state LiCl LiClO4 std. state Li2CO3 LiF std. state

Physical State

⌬fH⬚ kJ · mol⫺1

⌬fG⬚ kJ · mol⫺1

c c c c aq c c aq c c c aq c c c c c c c c c c c c c c

⫺699.2 ⫺851.4 ⫺930.9 ⫺664 ⫺666.9 ⫺941.8 ⫺175.5 ⫺112.1 ⫺1051.9 478.2 ⫺451.9 ⫺416.3 ⫺219.0 ⫺277.4 ⫺718.4 ⫺2595.3 ⫺100.4 ⫺102.9 ⫺609.2 ⫺1145.7 ⫺2023.8 ⫺1363.1 ⫺669.9 ⫺919.97(40) ⫺1182.0 ⫺70.7

⫺625.5 ⫺750.2

131.0 146.0

87.40 105.4

⫺617.1 ⫺582.0

110.5 ⫺17.2

72.3

⫺173.58 ⫺127.6 ⫺951.4 624.7

174.9 233.0 166.1 148.1

77.4

c g aq c c c c c c c c c c aq c aq c aq c aq c aq c aq

0 159.3(10) ⫺278.47(8) ⫺3317 ⫺116.3 ⫺1188.7 ⫺1651.8 ⫺190.8 ⫺415.5 ⫺2274 ⫺1032.2 ⫺3362 ⫺351.2 ⫺400.03 ⫺346.98 ⫺345.56 ⫺408.6 ⫺445.6 ⫺381.0 ⫺407.81 ⫺1215.9 ⫺1234.1 ⫺616.0 ⫺611.12

⫺246.9 ⫺188.9 ⫺217.3 ⫺601.2 ⫺2432.6 ⫺98.7 ⫺101.7 505.0 ⫺1062.1 ⫺1909.6 ⫺1252.6 ⫺813.0 ⫺69.5 0 ⫺293.30 ⫺3152 ⫺44.7 ⫺1126.3 ⫺1576.3 ⫺125.0 ⫺220.5 ⫺2171 ⫺976.1 ⫺3170 ⫺342.00 ⫺397.27 ⫺274.89 ⫺384.4 ⫺424.6 ⫺254 ⫺302.1 ⫺1132.12 ⫺1114.6 ⫺587.7 ⫺571.9

S⬚ J · deg⫺1 · mol⫺1

303.3 66.5 68.60 211.3 353.1 91.3 102.5 167.8 109.6 84.01 186.6

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

119.70

45.8 64.6 146.9 256.3 49.4 50.2 90.04 98.66 137.2

148.50(60) 225.06 110.0

103.2 150.16 50.5

29.12(20) 138.782(10) 12.24(15) 238.5 78.7 53.3 89.2 75.9 289 130.6 51.5 156 74.27 95.81

24.8

174.9 59.3 69.9 126 195.4 90.4 ⫺29.7 35.66 ⫺0.4

top of rh base of rh

68.6 215.7 83.2 67.78 91.8 82.6 135.3 59.8 183.0 48.91 ⫺73.2

48.03 ⫺67.8 105 ⫺7.5 99.1 41.6 ⫺38.1

short standard long

DEAN #37261

LEFT

(McGHP)

6.100

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance LiH LiI std. state LiIO3 std. state Li3N LiNO2 LiNO3 std. state Li2O Li2O2 LiOH std. state Li3PO4 Li2SiO3 Li2Si2O5 Li2SO4 std. state Li2TiO3 Lutetium Lu Lu3⫹ LuCl3 std. state LuI3 Lu2O3 Magnesium Mg Mg2⫹ std. state MgAl2O4 MgBr2 std. state MgBr2 · 6H2O MgCl2 std. state MgCl2 · 6H2O Mg(ClO4)2 std. state Mg(ClO4)2 · 6H2O MgCO3 MgC2O4 std. state MgF2 Mg2Ge MgH2 MgI2 std. state Mg3N2 MgNH4PO4 · 6H2O Mg(NO3)2 std. state

Physical State

⌬fH⬚ kJ · mol⫺1

c c aq c aq c c c aq c c c aq c c c c aq c

⫺90.5 ⫺270.4 ⫺333.67 ⫺503.38 ⫺499.82 ⫺164.6 ⫺372.4 ⫺483.1 ⫺485.9 ⫺597.9 ⫺634.3 ⫺484.9 ⫺508.40 ⫺2095.8 ⫺1648.1 ⫺2561 ⫺1436.4 ⫺1466.2 ⫺1670.7

c aq c aq c c

0 ⫺665.0 ⫺945.6 ⫺1167.0 ⫺548.0 ⫺1878.2

c g aq c c aq c c aq c c aq c c c aq c c c c aq c c c aq

0 147.1(8) ⫺467.0(6) ⫺2299 ⫺524.3 ⫺709.94 ⫺2410.0 ⫺641.3 ⫺801.15 ⫺2499.0 ⫺568.90 ⫺725.51 ⫺2445.6 ⫺1095.8 ⫺1269.0 ⫺1292.0 ⫺1124.2(12) ⫺108.8 ⫺75.3 ⫺364.0 ⫺577.22 ⫺461.1 ⫺3681.9 ⫺790.65 ⫺881.6

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

C⬚p J · deg⫺1 · mol⫺1

⫺68.45 ⫺270.3 ⫺344.8

20.04 86.8 124.7

27.96 51.0 ⫺73.6

⫺421.33 ⫺128.6 ⫺302.0 ⫺381.1 ⫺404.5 ⫺561.2 ⫺578.9 ⫺439 ⫺451.9

131.4 62.59 96.0 90.0 160.2 37.6 56.5 42.82 7.1

⫺55.2 75.27

⫺18.0

⫺1557.2 ⫺2417 ⫺1321.7 ⫺1331.2 ⫺1579.8

79.8 125.5 115.1 7.3 91.8

99.1 138.1 117.6 ⫺155.6 109.9

0 ⫺628.0

50.96 ⫺264.0

⫺1021.0

⫺96.0

⫺1789.1 0 ⫺454.8 ⫺2177 ⫺503.8 ⫺662.8 ⫺2056.0 ⫺591.8 ⫺717.1 ⫺2115.0 ⫺472.0 ⫺1863.1 ⫺1012.1 ⫺1128.8 1071.1 ⫺105.9 ⫺35.9 ⫺358.2 ⫺558.1 ⫺400.9 ⫺589.5 ⫺677.4

109.96 32.67(10) 148.648(3) ⫺137.(4) 89.0 117.2 26.8 397 89.63 ⫺25.1 315.1 225.4 520.1 65.7 ⫺92.5 57.2(5) 86.48 31.1 129.7 84.5 87.9 164.0 154.8

cap height base of text

70.6 49.7

26.86 25.0 ⫺385.0 101.75 24.87

116.20 73.16

71.38

75.51

61.5 69.54 35.4 74.8 104.5 141.9

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.101

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Mg(NO3)2 · 6H2O MgO microcrystal Mg(OH)2 std. state Mg3(PO4)2 MgS MgSeO4 std. state Mg2Si MgSiO3 clinoenstatite Mg2SiO4 forsterite Mg3Si4O10(OH)2 talc MgSO3 · 3H2O MgSO3 · 6H2O MgSO4 std. state MgSO4 · H2O kieserite MgSO4 · 7H2O epsomite MgTiO3 Mg2TiO4 MgTi2O5 Mg2V2O7 triclinic MgWO4 Manganese Mn Mn2⫹ std. state MnBr2 std. state Mn3C MnCl2 std. state MnCO3 Mn2(CO)10 MnF2 MnI2 Mn(NO3)2 std. state MnO MnO2 Mn2O3 MnO⫺4 MnO24⫺ Mn3O4 Mn3(PO4)2 MnS MnSe MnSiO3 MnSiO4 MnSO4 std. state MnTiO3

Physical State

⌬fH⬚ kJ · mol⫺1

c c c aq c c c aq c c c c c c c aq c c c c c c c

⫺2613.3 ⫺601.6(3) ⫺924.7 ⫺926.8 ⫺3780.7 ⫺346.0 ⫺968.51 ⫺1066.1 ⫺77.8 ⫺1548.9 ⫺2174.0 ⫺5922.5 ⫺1931.8 ⫺2817.5 ⫺1284.9 ⫺1376.1 ⫺1602.1 ⫺3388.71 ⫺1497.6 ⫺2164.0 ⫺2509 ⫺2835.9 ⫺1516

c aq c aq c c aq c c c c aq c aq c c c aq aq c c c c c c c aq c

0 ⫺220.75 ⫺384.9 ⫺464.0 ⫺4.6 ⫺481.3 ⫺555.05 ⫺894.1 ⫺1677.4 ⫺795.0 ⫺242.7 ⫺331.0 ⫺576.26 ⫺635.6 ⫺385.2 ⫺520.1 ⫺959.0 ⫺541.4 ⫺653.0 ⫺1387.8 ⫺3116.7 ⫺214.2 ⫺106.7 ⫺1320.9 ⫺1730.5 ⫺1065.3 ⫺1130.1 ⫺1355.6

⌬fG⬚ kJ · mol⫺1 ⫺2080.7 ⫺569.3 ⫺833.7 ⫺769.4 ⫺3538.8 ⫺341.8

S⬚ J · deg⫺1 · mol⫺1 452 26.95(15) 63.24 ⫺149.0 189.20 50.3

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1

37.2 77.25 213.47 45.6

⫺896.2 ⫺77.1 ⫺1462.0 ⫺2055.1 ⫺5543.0

⫺84.1 81.6 67.8 95.1 260.7

⫺1170.6 ⫺1199.5 ⫺1428.8 ⫺2871.9 ⫺1420.1 ⫺2048 ⫺2369 ⫺2645.29 ⫺1404

91.6 ⫺118.01 126.4 372 111.08 115.0 135.6 200.4 101.2

91.88 129 146.9 203.47 109.1

0 ⫺228.1 ⫺372 ⫺409.2 5.4 ⫺440.5 ⫺490.8 ⫺816.7

32.01 ⫺73.6 138.1

26.30 50 75.31

98.7 118.20 38.9 85.8

93.51 72.9 ⫺222 81.5

⫺749

92.26 150.6

67.99 75.35

⫺451.0 ⫺362.9 ⫺465.2 ⫺881.2 ⫺447.3 ⫺500.8 ⫺1283.2

218.0 59.8 53.1 110.5 191.2 59 155.6

⫺121.0 45.4 54.1 107.7 ⫺82.0

⫺218.4 ⫺111.7 ⫺1240.6 ⫺1632.1 ⫺957.42 ⫺972.8

78.2 90.8 89.1 163.2 112.1 ⫺53.6 105.9

50.0 51.0 86.4 129.9 100.4 ⫺243 99.8

67.9 81.9 118.5 321.8

96.5

139.7

short standard long

DEAN #37261

LEFT

(McGHP)

6.102

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Mercury Hg Hg2⫹ Hg⫹ HgBr2 Hg2Br2 Hg(CH3)2 Hg(C2H5)2 HgCl2 Hg2Cl2 Hg(CN)2 Hg2CO3 HgC2O4 HgF2 Hg2F2 HgI2 Hg2I2 Hg2(N3)2 HgO HgS HgSO4 Hg2SO4 HgTe Molybdenum Mo MoBr3 MoCl4 MoCl5 MoCl6 Mo(CO)6 MoF6 MoO2 MoO3 MoO24⫺ std. state MoS2 Mo2S3 Neodymium Nd Nd3⫹ std. state NdCl3 std. state NdF3 Nd(NO3)3 Nd2O3 Neon Ne Neptunium Np NpF6 NpO2

Physical State

⌬fH⬚ kJ · mol⫺1

⌬fG⬚ kJ · mol⫺1

lq g aq aq c c lq lq c c c c c c c c c c c c c c c

0 61.38(4) 170.21(20) 166.87(50) ⫺170.7 ⫺206.9 59.8 30.1 ⫺224.3 ⫺265.37(40) 263.6 ⫺553.5 ⫺678.2 ⫺405 ⫺485 ⫺105.4 ⫺121.3 594.1 ⫺90.79(12) ⫺58.2 ⫺707.5 ⫺743.09(40) ⫺42.0

c c c c c c lq c c aq c c

0 ⫺284 ⫺477 ⫺527 ⫺523 ⫺982.8 ⫺1585.66 ⫺588.9 ⫺745.2 ⫺997.9 ⫺235.1 ⫺270.3

0 ⫺259 ⫺402 ⫺423 ⫺391 ⫺877.8 ⫺1473.17 ⫺533.0 ⫺668.1 ⫺836.4 ⫺225.9 ⫺278.6

c aq c aq c c c

0 ⫺696.2 ⫺1041.0 ⫺1197.9 ⫺1657.0 ⫺1230.9 ⫺1807.9

0 ⫺671.5

71.6 ⫺206.7

⫺1065.7

⫺37.7

27.5 ⫺21 113 ⫺431

⫺1720.9

158.6

111.3

0 31.8

S⬚ J · deg⫺1 · mol⫺1

C⬚p J · deg⫺1 · mol⫺1

⫺153.1 ⫺181.1 140.2

75.90(12) 174.971(5) ⫺36.19(80) 65.74(80) 172.0 218.0 209

⫺178.6 ⫺210.7

146.0 191.6(8)

⫺468.1

180.0

⫺362 ⫺469 ⫺101.7 ⫺111.1 746.4 ⫺58.49 ⫺50.6 ⫺594 ⫺625.8

134.3 161 180.0 233.5 205 70.25(30) 82.4

74.86 100.4 77.75 105.9

200.70(20)

131.96

28.71 175 224 238 255 325.9 259.69 46.3 77.8 27.2 62.57 181.2

24.13 105.4 128 155.6 175 242.3 169.8 56.0 75.0

g

0

0

c c c

0 ⫺1937 ⫺1029

0 ⫺979

146.328(3)

cap height base of text

28.00 20.8

75.3 104.6

73.9 102.0

44.06 48.4

63.56 109.3

20.786 29.46

80.3

66.1

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.103

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Nickel Ni Ni2⫹ std. state Ni(OAc)2 std. state NiBr2 NiCl2 std. state Ni(CN)24⫺ std. state Ni(CO)4 NiC2O4 NiF2 NiI2 Ni(NO3)2 std. state NiO Ni2O3 NiOH⫹ Ni(OH)2 NiS Ni3S2 NiS2 NiSO4 std. state NiSO4 · 7H2O NiWO4 Niobium Nb NbBr5 NbC NbCl5 NbF5 NbI5 NbN NbO NbO2 Nb2O5 NbOCl3 Nitrogen N atomic N2 N⫺3 NCl3 NF2 NF3 H2NOH N2F2 cis trans

Physical State

⌬fH⬚ kJ · mol⫺1

c aq aq c aq c aq aq lq g c c aq c aq c aq c c aq c c c c c aq c c

0 ⫺54.0 ⫺1025.9 ⫺212.1 ⫺297.1 ⫺305.3 ⫺388.3 367.8 ⫺633.0 ⫺602.9 ⫺856.9 ⫺651.5 ⫺719.2 ⫺78.8 ⫺164.4 ⫺415.1 ⫺468.6 ⫺240.6 ⫺489.5 ⫺287.9 ⫺529.7 ⫺82.0 ⫺216.0 ⫺131.4 ⫺872.9 ⫺963.2 ⫺2976.3 ⫺1128.4

c c c c c c c c c c c

0 ⫺556 ⫺138.9 ⫺797.5 ⫺1813.8 ⫺268.6 ⫺236.4 ⫺405.8 ⫺796.2 ⫺1899.5 ⫺879.5

g g aq lq g g c g g

472.68(40) 0 275.1 230.0 43.1 ⫺132.1 ⫺114.2 69.5 82.0

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

29.87 ⫺128.9 44.4

⫺253.6 ⫺259.0 ⫺307.9 472.0 ⫺588.2 ⫺587.2

36.0 97.7 ⫺15.1 218 313 410.6

⫺604.2 ⫺603.3

73.6 ⫺156.5

⫺149.0

93.7

⫺268.6 ⫺211.7

164.0 38.00

44.31

⫺227.6 ⫺447.3 ⫺79.5 ⫺210 ⫺124.7 ⫺759.8 ⫺790.3 ⫺2462.2

⫺71.0 88.0 53.0 133.9 72 92.0 ⫺108.8 378.94 118.0

47.1 117.7 70.6 138.0 327.9 364.59 136.0

0 ⫺508 ⫺136.8 ⫺683.3 ⫺1699.0

36.4 258.8 34.98 210.5 160.3 343 34.5 48.1 54.5 137.3 159

24.67 147.9 36.23 148.1 134.7 155.6 39.0 41.3 57.45 132.0 120.0

26.1

71.66

404.6 145.2 64.1

153.301(3) 191.609(4) 107.9

29.124

57.8 ⫺90.6

249.9 260.8

41.0 53.37

109 120.5

259.8 262.6

49.96 53.47

0 348.2

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

0 ⫺45.6 ⫺784.5

⫺205.9 ⫺392.6 ⫺740.5 ⫺1765.8 ⫺782

top of rh base of rh

short standard long

DEAN #37261

LEFT

(McGHP)

6.104

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance N2F4 N2H4 hydrazine N22H4 hydrazine-d4 N2H5⫹ std. state N2H5Br std. state N2H5Cl std. state N2H5Cl · HCl N2H5OH undissoc; std. state N2H5NO3 std. state (N2H5)2SO4 std. state NO NOBr NOCl NOF NOF3 NO2 NO⫺2 NO2Cl NO2F NO3 NO⫺3 N2O N2O2 N2O22⫺ hyponitrite N2O3 N2O4 N2O5 NSF Osmium Os OsCl3 OsCl4 OsF6 OsO4 Oxygen O atomic O2 O3 OF2 O2F2 OH⫺ Palladium Pd Pd2⫹ std. state

Physical State

⌬fH⬚ kJ · mol⫺1

g lq g aq c aq c aq c lq aq c aq c aq g g g g g g aq g g g aq g g aq g lq g g g

⫺8.4 50.6 81.6 ⫺7.5 ⫺155.6 ⫺128.9 ⫺197.1 ⫺174.9 ⫺367.4 ⫺242.7 ⫺251.50 ⫺251.58 ⫺215.10 ⫺959.0 ⫺924.7 91.29 82.23 51.71 ⫺66.5 ⫺163 33.1 ⫺104.6 12.6 ⫺109 69.41 ⫺206.85(40) 81.6 170.37 ⫺17.2 86.6 ⫺19.5 11.1 11.3

c c c g c g g g g g g aq c aq

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1 301.2 121.2 248.86 151

⫺21.8

233.1

⫺71.6

⫺49.0

207.1

⫺66.1

⫺109.2

207.9

73.2

322 210.76 273.7 261.68 248.02 278.40 240.1 123.0 272.19 260.2 252.5 146.70(40) 220.0 287.52 27.6 314.7 209.20 304.38 355.7 259.8

0 ⫺190.4 ⫺254.8

0 ⫺121 ⫺159

⫺394.1 ⫺337.2

⫺305.0 ⫺292.8

32.6 130 155 358.1 143.9 293.8

24.5 18.0 ⫺230.015(40) 0 149.0

231.7 0 142.7 41.8 61.42 ⫺157.28 0 176.6

79.2 98.84 55.52 70.3

297

⫺579.9 87.60 82.42 66.10 ⫺51.0 ⫺96 51.3 ⫺32.2 54.4 ⫺66 114.35 ⫺111.3 103.7 202.88 138.9 142.4 97.5 99.8 117.1

249.18(10) 0

C⬚p J · deg⫺1 · mol⫺1

79.9 149.3 150.9 82.4

⫺28.91

cap height base of text

161.059(3) 205.152(5) 163.2 247.5 268.11 ⫺10.90(20) 37.61 ⫺184.0

⫺151 29.85 45.48 44.7 41.3 67.86 37.2 ⫺97.5 53.19 49.8 46.9 ⫺86.6 38.62 63.51 72.72 142.71 79.2 95.30 44.1 24.7

120.8 74.1 21.9 29.4 238.92 57.11 54.06 ⫺148.5 25.94

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.105

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance PdBr2 PdBr24⫺ std. state PdCl2 PdCl42⫺ std. state Pd2H PdO PdS PdS2 Phosphorus P white red, V P2 P4 PBr3 PBr5 PCl3 PCl5 PF3 PF5 PH3 std. state PH4Br PH4Cl PH4I PH4OH undissoc; std. state PI3 PO2 PO⫺3 PO34⫺ std. state P2O74⫺ std. state (P2O3)2 dimer P4O10 POBr3 POCl3 POClF2 POCl2F POF3 PSCl3 PSF3 P4S3 Platinum Pt PtBr2 PtBr3 PtBr4

Physical State c aq c aq c c c c c g c g g lq g c lq g c g g g g aq c c c aq c g aq aq aq c c c g lq g g g g g g c c c c c

⌬fH⬚ kJ · mol⫺1 ⫺104.2 ⫺384.9 ⫺171.5 ⫺550.2 ⫺19.7 ⫺85.4 ⫺75 ⫺81.2 0 316.5(10) ⫺17.46 144.0(20) 58.9(3) ⫺184.5 ⫺139.3 ⫺269.9 ⫺319.7 ⫺227.1 ⫺443.5 ⫺374.9 ⫺958 ⫺1594.4 5.4 ⫺9.50 ⫺127.6 ⫺145.2 ⫺69.9 ⫺295.35 ⫺45.6 ⫺279.9 ⫺977.0 ⫺1277.4 ⫺2271.1 ⫺1640.1 ⫺3009.9 ⫺458.6 ⫺389.11 ⫺597.1 ⫺558.5 ⫺970.7 ⫺765.7 ⫺1254.0 ⫺363.2 ⫺1009 ⫺155 0 ⫺82.0 ⫺120.9 ⫺156.5

⌬fG⬚ kJ · mol⫺1

⫺318.0 ⫺125.1 ⫺416.7 ⫺5.0 ⫺67 ⫺74.5 0 280.1 ⫺12.46

S⬚ J · deg⫺1 · mol⫺1

247 105 167 91.6 56.1 46 80

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

31.5

24.4 ⫺175.5 ⫺162.8

41.09(25) 163.1199(3) 22.85 218.123(4) 280.01(50) 240.2 348.15

⫺272.4 ⫺267.8

217.2 311.8

⫺305.0 ⫺937 ⫺1520.7 13.4 25.31 ⫺47.7

364.6 273.1 300.8 210.24 120.1 110.0

112.8 58.69 84.8 37.10

0.8 ⫺211.88

123.0 190.0

109.6

⫺281.6

252.1

39.5

⫺1018.8 ⫺1919.2

⫺220.5 ⫺117.0

⫺2723.3

top of rh base of rh

23.83 20.8 21.19 67.16 76.02

71.8

228.78

211.71

⫺390.91 ⫺520.9 ⫺512.9 ⫺924.1 ⫺721.6 ⫺1206 ⫺347.7 ⫺985 ⫺159

⫺359.84 222.46 325.5 301.68 320.38 285.4 337.23 298.1 201

89.87 138.82 84.94 68.83 79.32 68.82 89.83 74.55 146

41.63

25.87

short standard long

DEAN #37261

LEFT

(McGHP)

6.106

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance PtCl2 PtCl3 PtCl4 PtCl42⫺ PtCl24⫺ std. state PtCl26⫺ std. state PtF6 PtI4 PtS PtS2 Plutonium Pu Pu3⫹ Pu4⫹ PuBr3 PuCl3 PuCl4 PuF3 PuF4 PuF6 PuH2 PuH3 PuI3 PuO PuO2 Pu2O3 beta Pu(SO4)2 PuS Pu2S3 Polonium Po PoO2 Potassium K

K⫹ std. state KOAc acetate KAg(CN)2 KAgCl2 K2AgI3 KAlCl4 K3AlCl6 K3AlF6 KAl(SO4)2 K3AsO4 std. state KBF4 std. state KBH4 std. state

Physical State

⌬fH⬚ kJ · mol⫺1

c c c c aq aq g c c c

⫺123.4 ⫺182.0 ⫺3218 ⫺231.8 ⫺499.2 ⫺668.2

c aq aq c c c c c c c c c c c c c c c

0 ⫺579.9 ⫺579.9 ⫺831.8 ⫺961.5 ⫺1381 ⫺1552 ⫺1732 25.48 ⫺139.3 ⫺138 ⫺648.5 ⫺565 ⫺1058.1 ⫺1715.4 ⫺2200.8 ⫺439.3 ⫺989.5

c c c lq g aq c aq aq aq aq c c c c aq c aq c aq

⫺72.8 ⫺81.6 ⫺108.8

0 ⫺251 0 2.284 89.0(8) ⫺252.14(8) ⫺723.0 ⫺738.39 18.0 ⫺497.4 ⫺686.6 97 ⫺2092.0 ⫺3358.1 ⫺2470.2 ⫺1645.27 ⫺1887 ⫺1827.2 ⫺227.4 ⫺204.22

⌬fG⬚ kJ · mol⫺1

⫺134 ⫺172 ⫺361.5 ⫺482.8

⫺76.2 ⫺99.6 0 ⫺587.9 ⫺1490 ⫺804.6 ⫺892.7

S⬚ J · deg⫺1 · mol⫺1

C⬚p J · deg⫺1 · mol⫺1

117 151 176 155 220.1 348.3 55.06 74.68 51.5 ⫺163

122.8 43.39 65.90 35.5

192.88 159.00

107.86 102.84

⫺1478.8 ⫺1644.7 27.2 ⫺101.7 ⫺82.4 ⫺643.9 ⫺538.9 ⫺1005.8 ⫺1632.3 ⫺1969.5 ⫺436.7 ⫺985.5

112.97 161.9 222.59 59.8 64.9 214.2 70.7 82.4 152.3 163.18 78.24 192.46

96.82 120.8 167.36 39.0 43.2 111.8 51.3 68.6 131.0 181.96 53.97 129.66

0 ⫺197

62.8 71

26.4 61.5

0 0.264 ⫺283.26 ⫺652.66 22.2 ⫺498.7 ⫺720.5 ⫺1094 ⫺1938 ⫺2240.1 ⫺1498.29 ⫺1785 ⫺1770.3 ⫺160.2 ⫺168.99

cap height base of text

64.68(20) 71.46 160.341(3) 101.20(20)

29.60 32.72

189.1 297 333.9 458.1 197 377 284.5 204.47 144.8 133.9 285 106.31 212.97

15.5

21.8

156.4 248.9 221.1 192.92 114.48 96.57

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.107

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance KBO2 std. state K2B4O7 KBr std. state KBrO3 KBrO4 KCl std. state KClO std. state KClO2 std. state KClO3 std. state KClO4 std. state KCN std. state K2CO3 std. state K2C2O4 K2CrO4 std. state K2Cr2O7 K2CuCl4 · 2H2O KF std. state K3Fe(CN)6 std. state K4Fe(CN)6 std. state K formate std. state K glycinate KH K2HAsO4 std. state KH2AsO4 std. state KHCrO4 std. state KHCO3 std. state KHC2O4 std. state KHF2 KHgBr3 std. state K2HgBr4 std. state KHgCl3 std. state

Physical State c aq c c aq c aq c c aq aq aq c aq c aq c aq c aq c aq c aq c c c aq c aq c aq c aq aq c aq c aq aq c aq aq c aq c aq c aq c aq

⌬fH⬚ kJ · mol⫺1 ⫺981.6 ⫺1024.75 ⫺3334.2 ⫺393.8 ⫺373.92 ⫺360.2 ⫺319.45 ⫺287.86 ⫺436.5 ⫺419.53 ⫺359.4 ⫺318.8 ⫺397.73 ⫺356.35 ⫺432.8 ⫺381.71 ⫺113.1 ⫺101.7 ⫺1151.0 ⫺1181.90 ⫺1346.0 ⫺1329.72 ⫺1403.7 ⫺1385.91 ⫺2061.5 ⫺1707.1 ⫺567.2 ⫺585.01 ⫺249.8 ⫺139.4 ⫺594.1 ⫺554.0 ⫺679.73 ⫺677.93 ⫺722.16 ⫺57.72 ⫺1411.10 ⫺1180.7 ⫺1161.94 ⫺1130.5 ⫺963.2 ⫺944.33 ⫺1070.7 ⫺927.7 ⫺902.32 ⫺550.20 ⫺545.6 ⫺963.6 ⫺935.5 ⫺671.1 ⫺641.0

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺923.4 ⫺962.19 ⫺3136.8 ⫺380.7 ⫺387.23 ⫺271.2 ⫺264.72 ⫺174.47 ⫺408.5 ⫺414.51 ⫺320.1 ⫺266.1 ⫺296.31 ⫺291.29 ⫺303.1 ⫺291.88 ⫺101.9 ⫺110.9 ⫺1063.5 ⫺1094.41

79.98 65.3 208 95.9 184.9 149.2 264.22 170.01 82.55 159.0 146 203.8 143.1 264.9 151.0 284.5 128.52 196.7 155.5 148.1

⫺1295.8 ⫺1294.36 ⫺1882.0 ⫺1492.9 ⫺537.8 ⫺562.08 ⫺129.7 ⫺120.5 ⫺453.1 ⫺438.11

200.12 255.2 291.2 355.43 66.5 88.7 426.06 577.8 418.8 505.0

⫺634.3 ⫺598.23 ⫺53.01 ⫺1281.22 ⫺1036.0 ⫺1036.54 ⫺1048.1 ⫺863.6 ⫺870.10 ⫺981.7 ⫺859.7 ⫺861.40

192 221.8 50.21 203.3 155.02 218 286.6 115.5 193.7 251.9 104.3 195.0

⫺542.7

360

⫺937.6

515

⫺592.5

314

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1 66.7 170.5 52.3 ⫺120.1 105.2 120.2 51.29 ⫺114.6

100.3 112.41 66.3 114.44

145.98 219.2 253.22 48.98 ⫺84.9

322.2

⫺66.1 37.91 126.73

76.94

short standard long

DEAN #37261

LEFT

(McGHP)

6.108

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance K2Hg(CN)4 std. state K2HgI4 std. state KH2PO4 std. state K2HPO4 std. state K2H2P2O7 K3HP2O7 KHS std. state KHSO3 KHSO4 std. state KI KIO3 KIO4 KMnO4 K2MoO4 std. state KNH2 amide KNO2 std. state KNO3 std. state K2Ni(CN)4 std. state K2O KO2 K2O2 KOCN cyanate std. state KOH std. state K2PdBr4 std. state K3PO4 std. state K4P2O7 K2PtBr4 std. state K2PtBr6 std. state K2PtCl4 std. state K2PtCl6 std. state K2ReCl6 std. state

Physical State c aq c aq c aq aq c aq aq c aq aq c aq c aq c aq c aq c c aq c c aq c aq aq c c c c aq c aq c aq c aq aq c aq c aq c aq c aq c aq

⌬fH⬚ kJ · mol⫺1 ⫺32.2 21.8 ⫺775.0 ⫺739.7 ⫺1568.33 ⫺1548.67 ⫺1796.90 ⫺2815.8 ⫺2783.2 ⫺3032.1 ⫺265.10 ⫺269.9 ⫺878.60 ⫺1160.6 ⫺1139.72 ⫺327.9 ⫺307.57 ⫺510.43 ⫺473.6 ⫺467.23 ⫺403.8 ⫺837.2 ⫺1498.71 ⫺1502.5 ⫺128.9 ⫺369.82 ⫺356.9 ⫺494.63 ⫺459.74 ⫺136.8 ⫺361.5 ⫺284.9 ⫺494.1 ⫺418.65 ⫺398.3 ⫺424.7 ⫺482.37 ⫺938.1 ⫺889.5 ⫺1950.2 ⫺2034.7 ⫺3280.7 ⫺915.0 ⫺872.8 ⫺1021.3 ⫺975.3 ⫺1054.4 ⫺1003.7 ⫺1229.3 ⫺1171.8 ⫺1310.4 ⫺1266.92

⌬fG⬚ kJ · mol⫺1

51.9

S⬚ J · deg⫺1 · mol⫺1

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

510

⫺778.2 ⫺1415.95 ⫺1622.85 ⫺1655.78

565 134.85 192.9 171.5

⫺2576.9 ⫺2822.1

368 351

⫺271.21 ⫺811.07 ⫺1131.4 ⫺1039.26 ⫺324.9 ⫺334.85 ⫺418.4 ⫺411.3 ⫺361.41 ⫺341.8 ⫺737.6

165.3 242.3 138.1 234.3 106.3 213.8 151.46 220.9 175.7 322 171.71

⫺1402.9

232.2

116.57

75.3

⫺306.60 ⫺315.5 ⫺394.93 ⫺394.59 ⫺94.6 ⫺322.1 ⫺239.4 ⫺425.1

152.09 225.5 133.05 249.0 423 94.1 122.5 102.0

⫺380.7 ⫺378.7 ⫺440.53

209.2 78.9 91.6

⫺884.5

452

⫺1868.6 ⫺3052.2

87.9 293

⫺828.4

326.4

⫺898.7

368

⫺63.0 52.9 ⫺120.5 106.48

117.6

107.40 96.4 ⫺64.9 83.7 77.53 110

64.9 ⫺126.8

180.2 ⫺928.0 ⫺1078.6 ⫺1049.4 ⫺1172.8 ⫺1156.0

360 333.9 424.7 371.71 460

205.60 214.68

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.109

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance KReO4 std. state K2S std. state K2S2 KSCN std. state K2SeO3 std. state K2SeO4 std. state K2SiF6 std. state K2SiO3 K2SnBr6 K2SnCl6 K2SO3 std. state K2SO4 K2SO6 std. state K2S2O3 std. state K2S2O4 K2S2O7 K2S2O8 std. state K2S4O6 std. state KSO3F K2UO4 KVO4 std. state K2Zn(CN)4 std. state Praseodymium Pr Pr3⫹ std. state Pr(OAc)3 std. state PrCl3 std. state Pr(NO3)3 Pr2O3 Promethium PmCl3 Protactinium Pa Pa4⫹ PaBr4 PaBr5

Physical State

⌬fH⬚ kJ · mol⫺1

c aq c aq c aq c aq c aq c aq c aq c c c c aq c aq c aq c aq aq c c aq c aq c c c aq c aq

⫺1097.0 ⫺1039.7 ⫺380.7 ⫺471.5 ⫺432.2 ⫺474.5 ⫺200.16 ⫺175.94 ⫺979.5 ⫺1013.8 ⫺1110.02 ⫺1103.7 ⫺2956.0 ⫺2893.7 ⫺1548.1 ⫺1218.0 ⫺1477.0 ⫺1125.5 ⫺1140.1 ⫺1437.8 ⫺1414.0 ⫺1437.7 ⫺1414.02 ⫺1173.6 ⫺1156.9 ⫺1258.1 ⫺1986.6 ⫺1916.10 ⫺1849.3 ⫺1780.7 ⫺1728.8 ⫺1159.0 ⫺1921.3 ⫺1154.8 ⫺1140.6 ⫺100.0 ⫺162.3

c aq aq c aq c c

0 ⫺704.6 ⫺2147.52 ⫺1056.9 ⫺1206.3 ⫺1229.3 ⫺1809.6

c

⫺1054.0

c aq c c

0 ⫺619.2 ⫺824.0 ⫺862

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1 167.82 303.8 105.0 190.4

⫺487.0 ⫺178.32 ⫺190.58

233.5 124.26 246.9

88.53 ⫺18.4

⫺936.4 ⫺1002.9 ⫺1007.9 ⫺2798.7 ⫺2766.0 ⫺1455.7 ⫺1160.2 ⫺1333.0

218.0 222 259.0 225.9 327.2 146.1 443.1 366.5

118.4 246.0 246.0

⫺1053.1 ⫺1321.4 ⫺1311.1 ⫺1319.6 ⫺1311.14

176 175.6 225.1 175.5 225.1

131.5 ⫺251.0 131.3 ⫺251

⫺1089.1 ⫺1166.9 ⫺1791.6 ⫺1697.41 ⫺1681.6 ⫺1613.43 ⫺1607.1

272 297 255 278.7 449.4 309.66 462.3

⫺1066.9

155

⫺119.7

431

0 ⫺679.1 ⫺1805.56

73.2 ⫺209.0 164.9 ⫺42.0

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

⫺994.5 ⫺977.8 ⫺364.0 ⫺480.7

⫺1072.8

top of rh base of rh

122.55 8.4 74.7

213.2 230.79 ⫺24.3

27.20 ⫺29.0 100.0 ⫺439.0 117.40

0 ⫺787.9 ⫺820

51.8 234.0 289

short standard long

DEAN #37261

LEFT

(McGHP)

6.110

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance PaCl4 PaCl5 Radium Ra Ra2⫹ RaCl2 std. state Ra(NO3)2 std. state RaSO4 std. state Radon Rn Rhenium Re Re⫺ std. state ReBr3 ReCl3 ReCl26⫺ std. state ReO2 ReO3 Re2O7 Rhodium Rh RhCl3 Rh2O3 Rubidium Rb Rb⫹ std. state Rb acetate RbBO2 RbBr std. state RbBrO3 Rb2CO3 std. state RbCl std. state RbClO3 std. state RbClO4 std. state RbF std. state Rb formate RbHCO3 std. state RbHF2 std. state

Physical State

⌬fH⬚ kJ · mol⫺1

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

c c

⫺1043.1 ⫺1144.7

⫺953.0 ⫺1034.3

192.0 238.0

c aq aq c aq c aq

0 ⫺527.6 ⫺861.9 ⫺992 ⫺942.2 ⫺1471.1 ⫺1436.8

0 ⫺561.5 ⫺823.8 ⫺796.2 ⫺784.1 ⫺1365.7 ⫺1306.2

71 54.0 167.0 222 347.0 138 75.0

g

0

c g aq c c aq c c c g

0 769.9 46.0 ⫺167.0 ⫺264 ⫺761 ⫺423 ⫺605.0 ⫺1240.1 ⫺1100.0

c c c

0 ⫺299.2 ⫺343.0

c g aq aq c c aq c c aq c aq c aq c aq c aq aq c aq c aq

0 80.9(8) ⫺251.12(10) ⫺737.2 ⫺971.0 ⫺394.59 ⫺372.71 ⫺367.27 ⫺1136.0 ⫺1179.5 ⫺435.35 ⫺418.32 ⫺402.9 ⫺355.14 ⫺437.19 ⫺380.49 ⫺557.7 ⫺583.79 ⫺676.7 ⫺963.2 ⫺943.16 ⫺922.6 ⫺901.11

0

C⬚p J · deg⫺1 · mol⫺1

176.235

20.79

0 724.6 10.1

36.9 188.9 230.0

25.5 20.8

⫺188 ⫺590 ⫺368 ⫺531 ⫺1066.1 ⫺994.0

123.9 251 172 257.3 207.1 452.0

92.4

0

31.51 110.9

0 53.1 ⫺283.97 ⫺653.3 ⫺913.0 ⫺381.79 ⫺387.94 ⫺278.11 ⫺1051.0 ⫺1095.8 ⫺407.81 ⫺415.22 ⫺300.4 ⫺291.9 ⫺306.9 ⫺292.59 ⫺562.79 ⫺635.1 ⫺863.6 ⫺870.82 ⫺855.6 ⫺862.11

76.78(30) 170.094(3) 121.75(25) 207.9 94.3 109.96 203.93 161.1 181.33 186.2 95.90 178.0 151.9 283.68 161.1 303.3 75.3 107.53 213.0 121.3 212.71 120.08 213.8

cap height base of text

166.1

24.98 104.0 31.06 20.8

74.1 52.84

117.61 52.41 103.2

50.5

79.37

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.111

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance RbHSO4 std. state RbI std. state RbNO2 RbNO3 std. state Rb2O Rb2O2 RbOH std. state Rb2PtCl6 std. state RbReO4 std. state Rb2S Rb2SeO4 std. state Rb2SO4 std. state Ruthenium Ru RuBr3 RuCl3 RuI3 RuO2 RuO4 Samarium Sm Sm3⫹ std. state SmCl2 SmCl3 std. state SmF3 SmF3 · 1⁄2H2O SmI3 Sm(IO3)3 Sm(NO3)2 Sm2O3 Sm2(SO4)3 Scandium Sc Sc3⫹ std. state ScBr3 ScCl3 ScF3 ScOH2⫹ Sc2O3

Physical State

⌬fH⬚ kJ · mol⫺1

c aq c aq c c aq c c c aq c aq c aq aq c aq c aq

⫺1159.0 ⫺1138.51 ⫺333.8 ⫺306.35 ⫺367.4 ⫺495.05 ⫺458.52 ⫺339 ⫺472.0 ⫺418.19 ⫺481.16 ⫺1245.6 ⫺1170.7 ⫺1102.9 ⫺1038.5 ⫺469.4 ⫺1114.2 ⫺1101.7 ⫺1435.61 ⫺1411.60

c c c c c c lq

0 ⫺138.0 ⫺205.0 ⫺65.7 ⫺305.0 ⫺239.3 ⫺228.5

c aq c c aq c c

0 ⫺691.6 ⫺815.5 ⫺1025.9 ⫺1193.3 ⫺1778.0 ⫺1825.1

c c c c c

⫺620.1 ⫺1381 ⫺1212.1 ⫺1823.0 ⫺3899.1

c aq c c c aq c

0 ⫺614.2 ⫺743.1 ⫺925.1 ⫺1629.2 ⫺861.5 ⫺1908.8

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

⫺1039.98 ⫺328.9 ⫺335.56 ⫺306.2 ⫺395.85 ⫺395.30

253.1 118.4 232.6 172.0 147.3 267.8

⫺441.24 ⫺1109.6 ⫺1056.6 ⫺996.2 ⫺978.6 ⫺482.0

110.75 406 464 167 322.6 228.4

⫺1009.2 ⫺1316.96 ⫺1312.56

297.1 197.44 263.2

134.06

28.53

24.1

0

top of rh base of rh

53.18

102.1

⫺152.3 ⫺152.3

146.4 183.3

0 ⫺666.5

69.58 ⫺211.7

⫺1060.2

⫺42.7

⫺1734.7

151.0

0 ⫺586.6

34.64 ⫺255.0

25.52

121.3 92 ⫺134.0 76.99

93.64

⫺1555.6 ⫺801.2 ⫺1819.41

29.54 ⫺21

⫺431

114.5

94.2

short standard long

DEAN #37261

LEFT

(McGHP)

6.112

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Selenium Se SeBr2 SeCl4 SeF6 SeO SeO2 SeO3 SeO23⫺ std. state SeO24⫺ Silicon Si SiBr4 SiBrCl3 SiC alpha beta SiCl4 SiClBr3 SiClF3 SiF4 SiH4 SiHBr3 SiHCl3 SiHF3 SiH2Cl2 SiH3Cl SiH3F Si2H6 SiI4 Si3N4 SiO SiO2 quartz high cristobalite SiOF2 SiS2 Silver Ag Ag⫹ std. state Ag2⫹ in 4M HClO4 AgAt AgBr AgBrO3 AgCl AgClO2

Physical State

c g g c g g c c aq aq c g lq g g c c lq g g g g g g lq g g g g g g c lq c g c c g c c g aq aq c c c c c

⌬fH⬚ kJ · mol⫺1

0 227.1 ⫺21.0 ⫺188.3 ⫺1117.0 53.4 ⫺225.4 ⫺166.9 ⫺509.2 ⫺599.2

⌬fG⬚ kJ · mol⫺1

41.97 174.8

24.98 22.1

⫺1017.0 26.8

313.8 234.0

110.5 31.3

⫺369.9 ⫺441.4

13 54.0

⫺433.9 ⫺431.8

⫺62.8 ⫺65.3 ⫺686.93 ⫺657.0

⫺60.2 ⫺62.8 ⫺620.0 ⫺617.0

⫺1318 ⫺1615.0(8) 34.3 ⫺317.6 ⫺539.3 ⫺513.0

⫺1280 ⫺1572.7 56.8 ⫺328.5 ⫺482.5 ⫺482.0

0 284.9(8) 105.79(8) 268.6 ⫺45.2 ⫺100.37 ⫺10.5 ⫺127.01(5) 8.79

C⬚p J · deg⫺1 · mol⫺1

0 187.0

0 450.(8) ⫺457.3 ⫺415.5

⫺320.5 ⫺142 ⫺377 80.3 ⫺189.5 ⫺174.60 ⫺743.5 ⫺99.6 ⫺910.7(10) ⫺905.5 ⫺967 ⫺213.4

S⬚ J · deg⫺1 · mol⫺1

0

⫺295.0 ⫺119 ⫺353 127.2 ⫺191.6 ⫺187.49 ⫺642.1 ⫺126.4 ⫺856.4 ⫺853.6 ⫺951 ⫺212.6 0 77.12 269.0 ⫺96.90 71.3 ⫺109.8 75.7

18.81(8) 167.981(4) 277.5 377.9 350.1 16.49 16.61 239.7 330.7 377.1 309 282.76(50) 204.65 348.6 227.6 313.7 271.9 285.7 250.8 238.4 272.7 258.1 294.30 101.3 211.6 41.46(20) 50.05 271.3 80.3 42.55(20) 172.997(4) 73.45(40) ⫺88 133.1 107.11 151.9 96.25(20) 134.56

cap height base of text

20.00 146.4 97.1 90.9 26.76 26.9 145.3 90.26 95.3 79.4 73.62 42.83 80.8 75.8 60.5 60.5 51.10 47.20 80.79 108.0 159.79 99.5 29.9 44.4 26.58 53.69 77.5 25.4 21.8 55.7 52.38 50.79 87.32

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.113

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance AgClO3 AgClO4 std. state AgCN Ag(CN)⫺2 std. state Ag2CrO4 Ag2CO3 Ag2C2O4 AgF AgF2 AgI AgIO3 AgN3 Ag(NH3)2⫹ std. state AgNO3 std. state AgO Ag2O Ag2O3 Ag2S argentite Ag3Sb AgSCN Ag2Se Ag2SO4 std. state Ag2Te Sodium Na Na⫹ std. state NaAg(CN)2 std. state NaOAc std. state NaAlCl4 Na3AlCl6 NaAlF4 Na3AlF6 NaAlH4 NaAlO2 NaAl(SO4)2 std. state NaAlSiO4 NaAsO2 std. state Na3AsO4 std. state NaAu(CN)2 NaBF4 std. state NaBH4 std. state

Physical State c c aq c aq c c c c c c c c aq c aq c c c c c c c c aq c c g aq aq c aq c c g c c c aq c c aq c aq aq c aq c aq

⌬fH⬚ kJ · mol⫺1 ⫺30.3 ⫺31.13 ⫺23.77 146.0 270.3 ⫺731.74 ⫺505.9 ⫺673.2 ⫺204.6 ⫺360.0 ⫺61.84 ⫺171.1 308.8 ⫺111.29 ⫺124.4 ⫺101.80 ⫺12.15 ⫺31.1 33.9 ⫺32.59 ⫺23.0 87.9 ⫺38 ⫺715.9 ⫺698.10 ⫺37.2 0 107.5(7) ⫺240.34(6) 30.12 ⫺708.81 ⫺726.13 ⫺1142.0 ⫺1979.0 ⫺1869.0 ⫺3361.2 ⫺115.5 ⫺1137.3 ⫺2590 ⫺2092.8 ⫺660.53 ⫺669.15 ⫺1540 ⫺1608.50 2.1 ⫺1844.7 ⫺1812.1 ⫺188.6 ⫺199.60

⌬fG⬚ kJ · mol⫺1 64.5 68.49 156.9 305.4 ⫺641.83 ⫺436.8 ⫺584.1

⫺66.19 ⫺93.7 376.1 ⫺17.24 ⫺33.47 ⫺34.23 13.83 ⫺11.21 121.4 ⫺40.67 101.38 ⫺44.4 ⫺618.4 ⫺590.36 ⫺43.1 0 ⫺261.88 43.5 ⫺607.27 ⫺631.28 ⫺996.4 ⫺1829 ⫺1827.5 ⫺3136.7 ⫺1069.2 ⫺2238 ⫺1978.2

S⬚ J · deg⫺1 · mol⫺1 142.0 162.3 254.8 107.19 192 217.6 167.4 209 83.7 115.5 149.4 104.2 245.2 140.92 219.2 58.5 121.3 100.0 143.9 171.5 131.0 150.71 200.4 165.7 154.8 51.30(20) 153.718(3) 58.45(15) 251 123.0 145.6 188.3 347.0 345.7 239.5 70.40 ⫺222.6 124.3

⫺611.91

99.6

⫺1434.19 23.9 ⫺1750.1 ⫺1748.9 ⫺123.9 ⫺147.61

14.2 230 145.31 243 101.3 169.5

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1

66.73 142.26 112.26 51.92 56.82 102.93

93.05 ⫺64.9 44.0 65.86 76.53 101.7 63 81.76 131.4 ⫺251 87.5 28.15 46.4 79.9 40.2 154.98 244.1 105.9 215.89 73.64

120.3 86.8

short standard long

DEAN #37261

LEFT

(McGHP)

6.114

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance NaBO2 std. state NaBO3 · 4H2O Na2B4O7 std. state Na2B4O7 · 10H2O NaBr std. state NaBr3 std. state NaBrO std. state NaBrO3 std. state NaBrO4 std. state Na2[Cd(CN)4] NaCl std. state NaClO std. state NaClO2 std. state NaClO3 std. state NaClO4 std. state NaCN std. state Na3[Co(NO2)6] Na2CO3 Na2CO3 · H2O Na2CO3 · 10H2O Na2C2O4 std. state Na2CrO4 std. state Na2Cr2O7 std. state Na ethoxide NaF std. state Na3[Fe(CN)6] std. state Na4[Fe(CN)6] std. state Na formate std. state NaH Na2HAsO4 std. state NaH2AsO4 std. state NaHCO3 std. state NaHCrO4 std. state NaHF2 std. state

Physical State c aq c c aq c c aq aq aq c aq aq aq c aq aq c aq c aq c aq c aq c c aq c c c aq c aq c aq c c aq aq aq c aq c aq aq c aq aq c aq

⌬fH⬚ kJ · mol⫺1 ⫺977.0 ⫺1012.49 ⫺2114.2 ⫺3291.1 ⫺3271.1 ⫺6298.6 ⫺361.08 ⫺361.66 ⫺370.54 ⫺384.3 ⫺334.09 ⫺307.19 ⫺227.19 ⫺52.3 ⫺411.2 ⫺407.27 ⫺347.3 ⫺307.02 ⫺306.7 ⫺365.77 ⫺344.09 ⫺383.3 ⫺369.45 ⫺87.5 ⫺89.5 ⫺1423.0 ⫺1130.7 ⫺1157.4 ⫺1431.26 ⫺4081.32 ⫺1318.0 ⫺1305.4 ⫺1342.2 ⫺1361.39 ⫺1978.6 ⫺1970.7 ⫺413.80 ⫺576.6 ⫺572.75 ⫺158.6 ⫺505.0 ⫺666.5 ⫺666.67 ⫺56.34 ⫺1386.58 ⫺1149.68 ⫺950.81 ⫺932.11 ⫺1118.4 ⫺920.27 ⫺890.06

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

⫺920.7 ⫺940.81

73.54 21.8

⫺3096.0 ⫺3076.9 ⫺5516.6 ⫺349.00 ⫺365.85 ⫺368.95 ⫺295.4 ⫺242.6 ⫺243.34 ⫺143.93 ⫺16.3 ⫺384.1 ⫺393.17 ⫺298.7 ⫺244.8 ⫺262.34 ⫺269.91 ⫺254.9 ⫺270.50 ⫺76.4 ⫺89.5

189.0 192.9 586 86.82 141.4 274.5 100 128.9 220.9 ⫺258.57 439 72.1 115.5 100 115.9 160.3 123.4 221.3 142.3 241.0 115.6 153.1

⫺1044.4 ⫺1051.6 ⫺1285.41 ⫺3428.20

135.0 61.6 168.11 564.0

⫺1197.9 ⫺1235.0 ⫺1251.64

163.6 176.61 168.2

⫺1825.1

379.9

⫺546.3 ⫺540.70 ⫺56.5 ⫺352.63 ⫺600.00 ⫺613.0 ⫺33.55 ⫺1238.51 ⫺1015.16 ⫺851.0 ⫺848.72 ⫺1026.8 ⫺852.20 ⫺840.02

51.11 45.2 447.3 231.0 103.76 151 40.02 116.3 176 101.7 150.2 243.1 90.92 151.5

cap height base of text

C⬚p J · deg⫺1 · mol⫺1 65.94

186.8 614.5 51.38 ⫺95.4

50.51 ⫺90.0

111.3 70.4

112.3 145.60 550.32 142 142.13

46.85 ⫺60.3

82.68 ⫺41.4 36.39

87.61

75.02

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.115

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Na2H2[Fe(CN)6] NaH2PO4 std. state Na2HPO4 std. state Na2H2P2O7 NaHS std. state NaHSeO3 std. state NaHSeO4 std. state NaHSO4 std. state NaI std. state NaI3 NaIO3 std. state NaIO4 std. state Na methoxide std. state NaMnO4 std. state Na2MnO4 std. state Na2MoO4 std. state Na2Mo2O7 NaN3 std. state NaNH2 NaNbO3 std. state NaNO2 std. state NaNO3 std. state Na2[Ni(CN)4] NaO2 Na2O Na2O2 NaOCN cyanate std. state NaOH std. state Na3PO4 std. state Na4P2O7 std. state

Physical State aq c aq c aq c c aq c aq c aq c aq c aq aq c aq c aq c aq aq c aq c aq c c aq c c aq c aq c aq aq c c c c aq c aq c aq c aq

⌬fH⬚ kJ · mol⫺1 ⫺24.7 ⫺1536.8 ⫺1536.4 ⫺1748.1 ⫺1772.38 ⫺2764.8 ⫺237.23 ⫺257.73 ⫺759.23 ⫺754.67 ⫺821.40 ⫺821.74 ⫺1125.5 ⫺1127.46 ⫺287.9 ⫺295.31 ⫺291.6 ⫺481.79 ⫺461.50 ⫺429.28 ⫺391.62 ⫺367.8 ⫺433.59 ⫺781.6 ⫺1156.0 ⫺1134 ⫺1468.12 ⫺1478.2 ⫺2245.05 21.71 35.02 ⫺123.9 ⫺1315.9 ⫺1265.7 ⫺358.65 ⫺344.8 ⫺467.85 ⫺447.48 ⫺112.6 ⫺260.2 ⫺414.2 ⫺510.9 ⫺405.39 ⫺386.2 ⫺425.6 ⫺469.15 ⫺1917.40 ⫺1997.9 ⫺3188 ⫺3231.7

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

134.64 ⫺1386.2 ⫺1392.27 ⫺1608.3 ⫺1613.06 ⫺2522.5

335 127.49 149.4 150.50 84.5 220.20

⫺249.83

121.8

⫺673.41

194.1

⫺714.2 ⫺992.9 ⫺1017.88 ⫺286.1 ⫺313.47 ⫺313.4 ⫺389.95 ⫺323.09 ⫺320.49 ⫺294.80 ⫺332.46 ⫺709.2

208.4 113.0 190.8 98.50 170.3 298.3 135.1 177.4 163.0 280 110.58 17.6 250.2

⫺1024.7 ⫺1354.30 ⫺1360.2 ⫺2058.19 93.76 86.2 ⫺64.0 1233.0 ⫺1194.1 ⫺284.60 ⫺294.1 ⫺367.06 ⫺373.21 ⫺51.9 ⫺218.4 ⫺375.5 ⫺449.6 ⫺358.2 ⫺359.4 ⫺379.4 ⫺419.20 ⫺1788.87 ⫺1804.6 ⫺2969.4 ⫺2966.9

176 159.70 145.2 250.6 96.86 166.9 76.90 117 155 103.8 182.0 116.52 205.4 335 115.9 75.04 94.8 96.7 165.7 64.4 48.1 173.80 ⫺46 270.29 117

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1

116.86 135.31 198.15

⫺38 52.1 ⫺95.8 92.1

69.45

141.71 217.15 76.61 66.15

⫺51.0 92.88 ⫺40.2 72.14 69.10 89.3 86.6 59.5 ⫺102.1 153.47 241.12

short standard long

DEAN #37261

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(McGHP)

6.116

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SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance NaReO4 std. state Na2S std. state Na2S2 std. state NaSCN std. state Na2Se Na2SeO3 std. state Na2SeO4 Na2SiF6 Na2SiO3 Na2Si2O5 NaSnBr3 NaSnCl3 Na2SO3 std. state Na2SO4 std. state Na2SO4 · 10H2O Na2S2O3 std. state Na2S2O3 · 5H2O Na2S2O4 dithionate std. state Na2S2O7 Na2S2O8 Na2Te Na2TeO4 Na2TiO3 Na2UO4 beta Na3UO4 NaVO3 std. state Na3VO4 Na2V2O7 Na2WO4 Na2[Zn(CN)4] Strontium Sr Sr2⫹ std. state Sr(OAc)2 Sr3(AsO4)2 SrBr2 SrCl2 std. state Sr(ClO4)2 std. state

Physical State

⌬fH⬚ kJ · mol⫺1

c aq c aq c aq c aq c c aq c c c c aq aq c aq c aq c c aq c c aq c aq c c c c c c aq c c c aq

⫺1057.09 ⫺1027.6 ⫺364.8 ⫺443.3 ⫺397.0 ⫺450.2 ⫺170.50 ⫺163.68 ⫺341.4 ⫺958.6 ⫺989.5 ⫺1069.0 ⫺2909.6 ⫺1554.9 ⫺2470.1 ⫺615.1 ⫺727.2 ⫺1100.8 ⫺1115.87 ⫺1387.1 ⫺1389.51 ⫺4327.26 ⫺1123.0 ⫺1132.40 ⫺2607.93 ⫺1232.2 ⫺1233.9 ⫺1925.1 ⫺1825.1 ⫺349.4 ⫺1270.7 ⫺1591.2 ⫺1893.3 ⫺2025.1 ⫺1145.79 ⫺1128.4 ⫺1757.87 ⫺2918.84 ⫺1544.7 ⫺138.1

c aq c c c aq c aq c aq

0 ⫺545.8 ⫺1487.4 ⫺3317.1 ⫺717.6 ⫺788.89 ⫺828.9 ⫺880.10 ⫺762.69 ⫺804.46

⌬fG⬚ kJ · mol⫺1 ⫺953.74 ⫺956.5 ⫺349.8 ⫺438.1 ⫺392 ⫺444.3

S⬚ J · deg⫺1 · mol⫺1

C⬚p J · deg⫺1 · mol⫺1

151.5 260.2 83.7 103.3 151 146.4

133.89

⫺169.20

203.84

6.3

⫺893.7

130

⫺2754.2 ⫺1462.8 ⫺2324.1 ⫺608.8 ⫺692.0 ⫺1012.5 ⫺1010.44 ⫺1270.2 ⫺1268.40 ⫺3647.40 ⫺1028.0 ⫺1046.0 ⫺2230.1

207.1 113.8 164.1 310 318 145.94 87.9 149.6 138.1 592.0 155 184.1

⫺1124.2 ⫺1722.1 ⫺1638.9

209.2 202.1 362.3

⫺1496.2 ⫺1777.78 ⫺1901.2 ⫺1064.12 ⫺1045.6 ⫺1637.83 ⫺2712.52 ⫺1429.8 ⫺77.0

121.67 166.02 198.20 113.68 109 190.0 318.4 160.3 343

0 ⫺559.44

55.0 ⫺32.6

⫺3080.3 ⫺697.1 ⫺767.39 ⫺781.1 ⫺821.95

255 135.1 132.2 114.9 80.3

⫺576.68

331.4

cap height base of text

82.8

187.1 111.9 157.0

120.25 128.2 ⫺201

125.65 146.65 173.01 97.57 164.85 269.74 139.8

26.79

75.3 75.59

short standard long

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(McGHP)

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INTERACTIVE

6.117

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance SrCO3 SrC2O4 SrF2 Sr formate SrHPO4 Sr(H2PO4)2 SrI2 std. state Sr(IO3)2 SrMoO4 Sr(NO2)2 Sr(NO3)2 std. state SrO SrO2 Sr(OH)2 Sr3(PO4)2 SrS SrSe SrSeO3 SrSeO4 SrSiO3 Sr2SiO4 SrSO3 SrSO4 Sr2TiO4 Sulfur S rhombic monoclinic S22⫺ S2 S8 S2Br2 SCl2 SClF5 S2Cl2 SCN⫺ SF4 SF6 S2F10 SO SO2 SO3 SOCl2 SOF2 SO2Cl2 SO2ClF SO2F2

Physical State

⌬fH⬚ kJ · mol⫺1

c aq c c c c c c aq c c c c aq c c c c c c c c c c c c aq c

⫺1220.1 ⫺1222.9 ⫺1370.7 ⫺1216.3 ⫺1393.3 ⫺1821.7 ⫺3134.7 ⫺558.1 ⫺656.18 ⫺1019.2 ⫺1561.1 ⫺762.3 ⫺978.22 ⫺960.52 ⫺592.0 ⫺654.4 ⫺959 ⫺4122.9 ⫺472.4 ⫺385.8 ⫺1047.7 ⫺1142.7 ⫺1633.9 ⫺2304.6 ⫺1177.0 ⫺1453.1 ⫺1455.1 ⫺2287.4

c c g aq g g lq lq lq lq aq g g g g g g g g g g g

0 0.360 277.17(15) 33.1 128.60(30) 101.25 ⫺13.0 ⫺50.0 ⫺1065.7 ⫺59.4 76.4 ⫺763.2 ⫺1220.5 ⫺2064 6.3 ⫺296.81(20) ⫺395.7 ⫺212.50 ⫺544 ⫺364.0 ⫺556 ⫺759

⌬fG⬚ kJ · mol⫺1 ⫺1140.1 ⫺1087.3 ⫺1164 ⫺1688.7 ⫺557.7 ⫺662.62 ⫺855.2

⫺780.0 ⫺782.12 ⫺561.9

S⬚ J · deg⫺1 · mol⫺1 97.1 ⫺89.5 82.1

81.42

70.0

121 159.1 190.0 234 128.9

77.95

117.07 149.87

⫺881 ⫺467

68.2

48.7

⫺1549.8 ⫺2191.2

96.7 153.1

88.53 134.26

⫺1341.0 ⫺1304.0 ⫺2178.6

117.0 ⫺12.6 159.0

107.78

85.8 49.16 ⫺28.5 ⫺39 92.7 ⫺722.0 ⫺1116.5 ⫺1861 ⫺19.9 ⫺300.13 ⫺371.02 ⫺198.3 ⫺502 ⫺320.0 ⫺513 ⫺712

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

194.56 260.2 54.4 54 97

0 ⫺0.070

top of rh base of rh

32.054(50) 33.03 167.829(6) ⫺14.6 228.167(10) 430.20 184 224 144.3 299.6 291.5 397 222.0 248.223(50) 256.77 309.8 278.7 311.9 303 284.0

45.0 79.45 74.9

143.68 22.60 23.23

156.06 91.0 124.3 ⫺40.2 77.60 96.96 176.7 30.2 39.88 50.66 66.5 56.81 77.01 71.6 66.0

short standard long

DEAN #37261

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(McGHP)

6.118

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SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance SO32⫺ SO24⫺ S2O32⫺ S2O42⫺ S2O82⫺ Tantalum Ta TaB2 TaBr5 TaC Ta2C TaCl5 TaF5 Ta2H TaI5 TaN TaO2 Ta2O5 TaOCl3 Technetium Tc Tc2O7 Tellurium Te TeBr4 TeCl4 TeF6 TeO2 Te(OH)⫹3 Terbium Tb Tb3⫹ std. state TbCl3 std. state TbO2 Tb2O3 Tb2(SO4)3 std. state Thallium Tl Tl⫹ std. state Tl3⫹ std. state TlBr std. state TlBr3 TlBrO3 std. state TlCl std. state TlCl3 std. state TlClO3

Physical State

⌬fH⬚ kJ · mol⫺1

⌬fG⬚ kJ · mol⫺1

aq aq aq aq aq

⫺635.5 ⫺909.34(40) ⫺652.3 ⫺753.5 ⫺1344.7

⫺486.5 ⫺744.5 ⫺522.5 ⫺600.3 ⫺1114.9

c c c c c c c c c c g c g

0 ⫺209.2 ⫺598.3 ⫺144.1 ⫺197.5 ⫺859.0 ⫺1903.6 ⫺32.6 ⫺490 ⫺251 ⫺201 ⫺2046 ⫺780.7

c c

0 ⫺1113

c c c g c aq

0 ⫺190.4 ⫺326.4 ⫺1318.0 ⫺322.6 ⫺322.6

c aq c aq c c aq

0 ⫺682.8 ⫺997.1 ⫺1184.1 ⫺971.5 ⫺1865.2 ⫺4131.7

c aq aq c aq aq c aq c aq c aq aq

0 5.36 196.6 ⫺173.2 ⫺116.19 ⫺168.2 ⫺136.4 ⫺78.2 ⫺204.10 ⫺161.80 ⫺315.1 ⫺305.0 ⫺93.7

0

S⬚ J · deg⫺1 · mol⫺1 ⫺29.0 18.50(40) 67.0 92.0 244.3

C⬚p J · deg⫺1 · mol⫺1

⫺293.0

41.47 44.4 305.4 42.37 83.7 222 195.0 79.1 343 50.6 280 143.1 361.5

25.40 48.12 155.73 36.79 60.96 148 130.46 90.8 155.6 42.1 44.0 135.0 98.53

0

33.47

24.27

0

49.70

25.70

⫺270.3 ⫺496.1

209 335.77 79.5 111.7

138.5 116.90 63.89

0 ⫺651.9

73.22 ⫺226.0

28.91 17.0

⫺1045.6

⫺59.0

⫺142.7 ⫺746 ⫺69.0

⫺209 ⫺1911.0

cap height base of text

⫺393.0 115.9

⫺3597.4 0 ⫺32.38 214.6 ⫺167.36 ⫺136.36 ⫺97.1 ⫺53.14 ⫺30.5 ⫺184.93 ⫺163.64

64.18 125.5 ⫺192.0 120.5 207.9 54.0 168.6 288.7 111.30 182.00

⫺179.1 ⫺35.6

⫺23.0 287.9

26.32

50.50

50.92

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.119

THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Tl2CO3 TlF std. state TlI std. state TlNO3 Tl2O TlOH std. state Tl2S Tl2Se Tl2SO4 std. state Thorium Th Th4⫹ std. state ThBr4 ThC1.94 ThCl4 ThF3 ThF4 undissoc; std. state ThH2 ThI4 ThN Th3N4 Th(NO3)4 ThO2 ThOCl2 ThOF2 Th(OH)3⫹ Th(OH)22⫹ Th3P4 ThS2 Th2S3 Th(SO4)2 Thullium Tm Tm3⫹ std. state TmCl3 std. state Tm2O3 Tin Sn white gray Sn2⫹ in aqueous HCl Sn4⫹ in aqueous HCl SnBr2

Physical State c c aq c aq c aq c c aq c c c aq

⌬fH⬚ kJ · mol⫺1 ⫺700 ⫺324.6 ⫺327.27 ⫺123.9 ⫺49.83 ⫺243.93 ⫺202.0 ⫺178.7 ⫺238.9 ⫺224.64 ⫺97.1 ⫺59.0 ⫺931.8 ⫺898.56

c g aq c c c g c aq c c c c c c c c aq aq c c c c

0 602.(6) ⫺769.0 ⫺965.3 ⫺146 ⫺1186.2 ⫺1166.1 ⫺2097.8 ⫺2115.0 ⫺139.8 ⫺664.8 ⫺391.2 ⫺1315.0 ⫺1441.4 ⫺1226.4(35) ⫺1232.2 ⫺1665.2 ⫺1030.1 ⫺1282.4 ⫺1140.2 ⫺626.3 ⫺1083.7 ⫺2542.6

c aq c aq c

0 ⫺697.9 ⫺986.6 ⫺1199.1 ⫺1888.7

c aq c aq aq c

0 301.2(15) ⫺2.09 ⫺8.9(10) 30.5 ⫺243.5

⌬fG⬚ kJ · mol⫺1 ⫺614.6 ⫺311.21 ⫺125.39 ⫺83.97 ⫺152.46 ⫺143.7 ⫺147.3 ⫺195.8 ⫺189.66 ⫺93.7 ⫺59.0 ⫺830.48 ⫺809.40 0

S⬚ J · deg⫺1 · mol⫺1 155.2 83.3 111.7 127.6 236.8 160.7 272.0 126 88 114.6 151.0 172.0 230.5 271.1

⫺705.1 ⫺927.2 ⫺147.7 ⫺1094.1 ⫺1160.6 ⫺2003.4 ⫺1947.2 ⫺100.0 ⫺655.2 ⫺363.6 ⫺1212.9

51.8(5) 190.17(5) ⫺422.6 230 68.49 190.4 339.2 142.05 ⫺105 50.71 255 56.07 201

⫺1169.20 ⫺1156.0 ⫺1589.5 ⫺920.5 ⫺1140.9 ⫺1112.9 ⫺620.1 ⫺1077.0 ⫺2310.4

65.23(20) 123.4 105 ⫺343.0 ⫺218.0 221.8 96.2 180 159.0

0 ⫺661.9

74.01 ⫺243.0

⫺1055.6 ⫺1794.5

⫺75.0 139.8

0 0.13 ⫺27.2 2.5

51.08(8) 168.492(4) 44.14 ⫺16.7(40) ⫺117

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1

54.77 52.51 99.50

27.32

56.69 120.3 73.3 110.7 36.69 45.2 155.90 61.76 91.25

173.47 27.03 25.0 ⫺385.0 116.7 26.99 25.77

short standard long

DEAN #37261

LEFT

(McGHP)

6.120

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance SnBr4 SnCl2 std. state SnCl4 SnH4 SnI2 SnI4 SnO tetragonal SnO2 tetragonal Sn(OH)⫹ Sn(OH)2 SnS SnS2 Titanium Ti TiB TiB2 TiBr2 TiBr3 TiBr4 TiC TiCl2 TiCl3 TiCl4 TiF3 TiF4 TiH2 TiI4 TiN TiO TiO2 Ti2O3 Ti3O5 Tungsten W WBr5 WBr6 W(CO)6 WCl4 WCl5 WCl6 WF6 WO2 WO3 WO24⫺ WOCl4

Physical State c g c aq lq g g c g c c aq c c c

⌬fH⬚ kJ · mol⫺1

⌬fG⬚ kJ · mol⫺1

⫺377.4 ⫺314.6 ⫺325.1 ⫺329.7 ⫺511.3 ⫺471.5 162.8 ⫺143.5

⫺350.2 ⫺331.4

⫺280.71(20) ⫺577.63(20) ⫺286.2 ⫺561.1 ⫺100 ⫺167.4

⫺251.9 ⫺515.8 ⫺254.8 ⫺491.6 ⫺98.3

c g c c c c c c c c lq g c c c c c c c c c

0 473.(3) ⫺160 ⫺280 ⫺402 ⫺548.5 ⫺616.7 ⫺184 ⫺513.8 ⫺720.9 ⫺804.2 ⫺763.2(30) ⫺1435 ⫺1649 ⫺144 ⫺375 ⫺265.8 ⫺519.7 ⫺944.0(8) ⫺1520.9 ⫺2459.4

c c c c c c c lq g c c aq c

0 ⫺312 ⫺348.5 ⫺953.5 ⫺443 ⫺515 ⫺602.5 ⫺1747.7 ⫺1721.7 ⫺589.9 ⫺842.9 ⫺1075.7 ⫺671

⫺299.6 ⫺440.2 ⫺432.2 188.3

0 ⫺160 ⫺275 ⫺383 ⫺523.8 ⫺589.5 ⫺180 ⫺464.4 ⫺653.5 ⫺737.2 ⫺726.3 ⫺1362 ⫺1559 ⫺105.1 ⫺371.5 ⫺243.8 ⫺495.0 ⫺888.8 ⫺1434.2 ⫺2317.4 0 ⫺270 ⫺290.8 ⫺360 ⫺402 ⫺456 ⫺1631.4 ⫺1631.4 ⫺533.86 ⫺764.1 ⫺549

S⬚ J · deg⫺1 · mol⫺1

cap height base of text

C⬚p J · deg⫺1 · mol⫺1

264.4 411.9 130 172 258.6 365.8 227.7

136.44 103.4 79.33

446.1 57.17(30) 49.04(10) 50.0 155.0 77.0 87.4

105.4 44.31 52.59

30.72(10) 180.298(10) 35 28.5 108 176.6 243.5 24.2 87.4 139.7 252.3 353.2(40) 88 133.96 29.71 249.4 52.73 50.0 50.62(30) 78.8 129.3

25.0

165.3 98.3 48.95

49.25 70.12

29.7 44.3 78.7 101.7 131.5 33.81 69.8 97.2 145.2 95.4 92 114.27 30.09 125.6 37.08 39.9 55.0 97.4 154.8

32.6 272 314 331.8 198.3 217.6 238.5 251.5 341.1 50.5 75.9

24.3 155 181.4 242.5 129.7 155.6 175.4

173

146

119.0 56.1 73.8

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THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance WOF4 WO2Cl2 Uranium U U3⫹ U4⫹ UB2 UBr3 UBr4 UBr5 UC UCl3 UCl4 UCl5 UCl6 UF3 UF4 UF5 UF6 UH3 UI3 UI4 UN UO2 UO22⫹ std. state UO3 gamma U3O7 U3O8 U4O9 UOBr2 UOCl2 UOF2 UO2(OAc)2 UO2Br2 UO2Cl2 std. state UO2CO3 std. state UO2C2O4 UO2F2 std. state UO2(NO3)2 std. state UO2(OH)2 std. state UO2SO4 std. state US2 US3

Physical State

⌬fH⬚ kJ · mol⫺1

c c

⫺1407 ⫺780

c g aq aq c c c c c c c aq c c c c c c c c c c c aq c c c c c c c c c c aq c aq c c aq c aq aq c aq c c

0 533.(8) ⫺489.1 ⫺591.2 ⫺161.6 ⫺699.2 ⫺802.5 ⫺810.9 ⫺98.3 ⫺866.5 ⫺1019.2 ⫺1259.8 ⫺1058 ⫺1092 ⫺1502.1 ⫺1921.2 ⫺2075.3 ⫺2197.0 ⫺127.2 ⫺460.7 ⫺512.1 ⫺290.8 ⫺1085.0(10) ⫺1019.0(15) ⫺1223.8(12) ⫺3427.1 ⫺3574.8(25) ⫺4510.4 ⫺973.6 ⫺1066.9 ⫺1499.1 ⫺1963.55 ⫺1137.6 ⫺1243.9 ⫺1353.9 ⫺1691.2 ⫺1696.6 ⫺1796.94 ⫺1653.5 ⫺1684.0 ⫺1349.3 ⫺1434.3 ⫺1479.5 ⫺1845.1 ⫺1928.8 ⫺527 ⫺549.4

⌬fG⬚ kJ · mol⫺1 ⫺1298 ⫺703 0

S⬚ J · deg⫺1 · mol⫺1 176.0 200.8

⫺476.2 ⫺531.9 ⫺159.4 ⫺673.6 ⫺767.8 ⫺769.9 ⫺99.2 ⫺799.1 ⫺930.1 ⫺1056.8 ⫺950 ⫺962 ⫺1433.4 ⫺1823.3 ⫺1958.6 ⫺2068.6 ⫺72.8 ⫺459.8 ⫺506.7 ⫺265.7 ⫺1031.8 ⫺953.5 ⫺1145.7 ⫺3242.9 ⫺3369.8 ⫺4275.1 ⫺929.7 ⫺996.2 ⫺1428.8

50.20(20) 199.79(10) ⫺188.0 ⫺410.0 55.52 192 238.0 293 59.20 159.0 197.1 ⫺184.0 242.7 285.8 123.43 151.67 199.6 227.6 63.68 222 264 62.43 77.03(20) ⫺98.2(30) 96.11(40) 250.5 282.55(50) 334.1 158.00 138.32 119.2

⫺1066.5 ⫺1146.4 ⫺1215.9 ⫺1562.7 ⫺1481.6

169.5 150.5 15.5 138 ⫺154.4

⫺1557.4 ⫺1551.3 ⫺1105.0 ⫺1176.1 ⫺1267.8 ⫺1683.6 ⫺1698.3 ⫺526.4 ⫺547.3

135.56 ⫺125.1 243 195.4 ⫺118.8 154.8 ⫺77.4 110.42 138.49

top of rh base of rh cap height base of text

C⬚p J · deg⫺1 · mol⫺1 133.6 104.4 27.66

55.77 108.8 128.0 160.7 50.12 102.5 122.0 144.6 175.7 95.10 116.02 132.3 166.8 49.29 112.1 134.3 47.57 63.60 81.67 215.5 238.36 293.3 98.00 95.06

107.86

103.22

145.2 74.64 95.60

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SECTION 6

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance Vanadium V VBr4 VCl2 VCl3 VCl4 VF5 VN VO VO2 VO2⫹ std. state VO22⫹ std. state VO⫺3 std. state V2O3 V2O4 V2O5 V3O5 VOCl3 VOSO4 Xenon Xe XeF2 XeF4 XeF6 XeO3 XeOF4 Ytterbium Yb Yb2⫹ std. state Yb3⫹ std. state Yb(OAc)3 undissoc; std. state YbCl2 YbCl3 std. state Yb(NO3)3 std. state Yb2O3 Yttrium Y Y3⫹ std. state YCl3 YF3 Y2O3 Y(OH)3 Zinc Zn Zn2⫹ std. state

Physical State

⌬fH⬚ kJ · mol⫺1

c g c c lq lq g c c c aq aq aq c c c c lq g c

0 ⫺336.8 ⫺452 ⫺580.7 ⫺569.4 ⫺1480.3 ⫺1433.9 ⫺217.15 ⫺431.8 ⫺717.6 ⫺649.8 ⫺486.6 ⫺888.3 ⫺1218.8 ⫺1427 ⫺1550 ⫺1933 ⫺734.7 ⫺695.6 ⫺1309.2

g c c c g c lq

0 ⫺164.0 ⫺261.5 ⫺360 ⫺297 402 146

c aq aq aq

⫺674.5 ⫺2105.0

c c aq aq c

⫺799.6 ⫺959.8 ⫺1176.1 ⫺1296.6 ⫺1814.6

c aq c c c c

0 ⫺723.4 ⫺1000 ⫺1718.8 ⫺1905.31 ⫺1435

c g aq

0

0 130.40(40) ⫺153.39(20)

⌬fG⬚ kJ · mol⫺1

0 ⫺406 ⫺511.3 ⫺503.8 ⫺1373.2 ⫺1369.8 ⫺191.08 ⫺404.2 ⫺587.0 ⫺446.4 ⫺783.7 ⫺1139.3 ⫺1318.4 ⫺1419.3 ⫺1803 ⫺668.6 ⫺659.3 ⫺1169.9 0

S⬚ J · deg⫺1 · mol⫺1

C⬚p J · deg⫺1 · mol⫺1

28.94

24.90

97.1 131.0 255.0 175.7 320.9 37.28 39.0 51.5 ⫺42.3 ⫺133.9 50.2 98.3 103 130 163 244.4 344.4 108.8

72.22 93.18 161.7

169.685(3)

cap height base of text

98.58 38.00 45.5 62.59

103.2 115.4 130.6 150.62 89.9

20.786

⫺123.0

0 ⫺527.0 ⫺643.9 ⫺1772.84

238.0 183.3

25.0

⫺1037.6

⫺71.0

⫺385.0

⫺1726.7

133.1

115.35

0 ⫺693.7

44.4 ⫺251.0 136.8 100 99.08 99.2

26.51

⫺1644.7 ⫺1816.65 ⫺1291 0 ⫺147.1

59.87

41.63(15) 160.990(4) ⫺109.8(5)

26.74

75.0 102.51

25.40 46.0

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THERMODYNAMIC PROPERTIES

TABLE 6.3 Enthalpies and Gibbs Energies of Formation, Entropies, and Heat Capacities of the Elements and Inorganic Compounds (Continued)

Substance ZnBr2 std. state ZnCl2 std. state Zn(CN)24⫺ std. state ZnCO3 ZnF2 std. state ZnI2 Zn(NO3)2 ZnO Zn(OH)2 std. state ZnS sphalerite wurtzite ZnSe ZnSO4 Zn2SiO4 Zirconium Zr ZrB ZrBr2 ZrBr4 ZrC ZrCl2 ZrCl3 ZrCl4 ZrF2 ZrF4 ZnH2 ZrI2 ZrI3 ZrI4 ZrN ZrO2 ZrSiO4 ZrSO4

Physical State

⌬fH⬚ kJ · mol⫺1

c aq c aq aq c c aq c aq c aq c c aq c c c c aq c

⫺328.65 ⫺396.98 ⫺415.05 ⫺488.19 342.3 ⫺812.78 ⫺764.4 ⫺819.14 ⫺208.03 ⫺264.3 ⫺483.7 ⫺568.6 ⫺350.46(27) ⫺641.91 ⫺613.88 ⫺205.98 ⫺192.6 ⫺163 ⫺982.84 ⫺1063.2 ⫺1636.7

c c c c c c c c c c c c c c c c c c

0 ⫺322 ⫺405 ⫺760.7 197 ⫺502.0 ⫺714 ⫺981 ⫺962 ⫺1911.3 ⫺169.0 ⫺259 ⫺397.5 ⫺488 ⫺365 ⫺1100.6 ⫺2033.4 ⫺2217.1

⌬fG⬚ kJ · mol⫺1

S⬚ J · deg⫺1 · mol⫺1

C⬚p J · deg⫺1 · mol⫺1

⫺312.13 ⫺354.97 ⫺369.45 ⫺409.53 446.9 ⫺731.57 ⫺713.3 ⫺704.67 ⫺208.95 ⫺250.2

138.5 52.72 111.46 0.84 226 82.4 73.68 ⫺139.8 161.1 110.5

65.7 ⫺238.0 71.34 ⫺226.0

⫺369.6 ⫺320.52 ⫺553.59 ⫺461.62 ⫺201.29

180.7 43.65(40) 81.2 ⫺133.5 57.7

⫺163 ⫺871.5 ⫺891.6 ⫺1523.2

84.0 110.5 ⫺92.0 131.42

0 ⫺318.2 ⫺382 ⫺725.3 ⫺193 ⫺386 ⫺646 ⫺890 ⫺913 ⫺1810.0 ⫺128.8 ⫺258 ⫺394.9 ⫺485.4 ⫺336.7 ⫺1042.8 ⫺1919.1

39.0 35.94 116 224 33.32 110 146 181.4 75 104.7 35.0 150.2 204.6 260 38.86 50.36 84.1

top of rh base of rh cap height base of text

79.71 65.7 ⫺167.0 65.69 ⫺238.0 ⫺126.0 40.25 ⫺251 46.02

99.2 ⫺247.0 123.3 25.40 48.24 86.7 124.8 37.90 72.6 96 119.8 66 103.6 31.0 94.1 103.8 127.8 40.44 56.19 98.7 172.0

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SECTION 6

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds

cap height base of text

Abbreviations Used in the Table ⌬Hm, enthalpy of melting (at the melting point) in kJ · mol⫺1 ⌬Hv, enthalpy of vaporization (at the boiling point) in kJ · mol⫺1 ⌬Hs, enthalpy of sublimation (or vaporization at 298 K) in kJ · mol⫺1 Cp, specific heat (at temperature specified on the Kelvin scale) for the physical state in existence (or specified: c, lq, g) at that temperature in J · K⫺1 · mol⫺1 ⌬Ht, enthalpy of transition (at temperature specified, superscript, measured in degrees Celsius) in kJ · mol⫺1 Cp Substance Aluminum Al Al(BH4)3 Al6BeO10 AlBr3 Al4C3 AlCl3 AlF3 , ⌬Ht ⫽ 0.56455 AlI3 AlN Al2O3 corundum AlOCl Al2SiO5 andalusite kyanite sillimanite Al6Si2O13 mullite Al2S3 Al2TiO5 Americium Am Ammonium NH3 ND3 ammonia-d3 NH4Br, ⌬Ht ⫽ 3.22138 NH4Cl, ⌬Ht ⫽ 1.046⫺30.6 ⌬Ht ⫽ 3.950184.6 NH4ClO4 NH4I, ⌬Ht ⫽ 2.93⫺13 NH4NO3 Antimony Sb SbBr3 SbCl3 SbCl5 SbH3 SbI3 Sb2O3, ⌬Ht ⫽ 7.1573 Sb2S3 Argon Ar

⌬Hm 10.7l 402 11.25 35.4 98 15.9

⌬Hv 294.0 30

⌬Hs 326.4

23.5 116 32.2

112

111.4

55

400 K

600 K

800 K

1000 K

25.8

27.9

30.6

34.9(lq)

324.3 125.0 138.5 100.1 86.3 108.5 36.7 96.1 64.3 149.6 148.3 147.5 390.7 115.0 162.0

380.6 125.0 159.2 117.7 97.3 121.3 43.5 112.5 72.6 174.5 176.2 173.0 459.8 124.1 182.8

407.8 125.0 169.7 135.2 98.5

425.2 125.0 176.1 152.8 100.8

46.8 120.1 76.9 186.1 188.3 185.0 494.1 129.7 192.9

48.5 124.8 79.3 194.0 196.2 193.5 513.4 134.0 200.0

38.7 42.9

45.3 51.5

51.1 58.6

56.2 64.3

103.3

117.7

14.39 5.66

23.35

19.86

103

168.5525

20.9 6.40 19.87 14.6 12.7 10.0 22.8 54.4

1.12

193.43 59 45.2 48.4 21.3 68.6 74.6

6.43

148.7 89.0

25.9 125.5(lq) 123.4(lq)

106.6(lq) 108.5 123.3 20.8

27.7 81.6(g) 81.6(g)

29.5 82.2 82.2

143.5(lq) 82.2(g) 122.8 137.1 134.4 145.4 20.8

20.8

31.4 82.5 82.5

82.5(g) 150.6

20.8

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THERMODYNAMIC PROPERTIES

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance Arsenic As AsBr3 AsCl3 AsF3 AsF5 AsH3 AsI3 As2O3 Barium Ba BaBr2 BaCl2, ⌬Ht ⫽ 16.9925 BaCO3, ⌬Ht ⫽ 18.8806 BaF2, ⌬Ht ⫽ 2.671207 BaH2 BaI2 BaMoO4 BaO Ba(OH)2 BaS BaSO4 BaTiO3, ⌬Ht ⫽ 0.06775 Beryllium Be BeAl2O4, chrysoberyl BeBr2 Be2C BeCl2, ⌬Ht ⫽ 6.8403 BeF2, ⌬Ht ⫽ 0.92227 BeI2 Be3N2 BeO, ⌬Ht ⫽ 6.72100 BeS Be2SiO4 BeSO4, ⌬Ht ⫽ 1.113590 ⌬Ht ⫽ 19.55635 BeWO4 Bismuth Bi BiBr3 BiCl3 BiI3 Bi2O3, ⌬Ht ⫽ 116.7717 Bi2S3 Bi2Te3 Boron B BBr3 B4C

⌬Hm 24.44 11.7 10.1 10.4

⌬Hv

⌬Hs

25.6 41.8 35.0 29.7 20.8 16.7 59.3

133.5(lq)

45.4

18.4 140.3

46 16 63 40

246.4 285.4

405.1

43.9

302.5

330.6

424.3

297

291

100.0

515

105 199.4 70.5

136.0 125

6

11.30 21.7 10.9

151 75.4 72.6 20.9

27.5

29.3

88.3(g)

88.3

53.2

58.8

1000 K

63.9

33.9(c) 83.5 80.4 113.0 80.3

87.9 84.3 124.2 84.9

79.5 129.5 49.9 112.6

83.5 143.5 53.2 122.7(c)

87.5(c) 113.0(lq) 152.2 159.3 55.4 57.1 141.0(lq)

119.4 111.5

131.6 121.8

135.9 126.1

20.0 130.3 70.6 47.6 68.7 62.5 76.9 84.4 33.8 120.8 103.9 103.9

23.3 155.0 77.6(c) 51.9 75.8(c) 67.5 84.2 106.5 42.4 149.2 126.8 126.8

25.5 27.3 166.8 174.2 113.0(lq) 113.0 64.7 73.2 121.4(lq) 121.4 74.1(c) 85.6(lq) 117.6 46.7 166.0 149.8 149.8

123.6 49.3 174.1 174.4 174.4

113.0

131.3

142.9

153.0

31.8

31.8

123.6 136.2 179.7

130.3 141.3 192.3

137.0 146.4

20.8 77.6 98.4

23.4 79.8 107.7

25.0 81.1 114.3

116.9 131.1 164.3

120.5

105

800 K

33.2 79.2 77.3 99.0 75.9

27.0(c)

28.5

50.2

600 K

116.4

7.12 32.2 15.85 40 17.8 25 26.5

7.895 170.0 18 75.3 8.66 4.77 18 129.3 86

400 K

480 30.5

552

15.7 72.6(g) 76.4

31.8(lq)

39.1(lq) 92.2 89.5 134.6 94.6

137.9 128.7

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SECTION 6

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

cap height base of text

Cp Substance

⌬Hm

BCl3 BF3 F2B-BF2 BH3 B2H6 B4H9 B4H10 B5H11 B10H14 BI3 BN B3N3H6 borazine B2O3 B3O3H3 boroxin Bromine Br2 BrCl BrF BrF3 BrF5 Cadmium Cd CdBr2 CdCl2 CdF2 CdI2 Cd(NO3)2 · 4H2O CdO CdS CdSO4 Calcium Ca, ⌬Ht ⫽ 0.934 Ca(BO2)2 CaB4O7 CaBr2 CaC2 carbide CaCl2 CaCN2 cyanamide CaCO3 CaF2, ⌬Ht ⫽ 4.81151 CaH2 CaI2 Ca[Mg(CO3)2] dolomite CaMoO4 Ca3N2 Ca(NO3)2 CaO Ca(OH)2, ⌬Hdec ⫽ 99.2 Ca3(PO4)2, ⌬Ht ⫽ 15.51100 CaS

2.10 4.20

23.8 19.3 28

4.44 6.13

14.3 28.4 27.1 31.8 48.5 40.5

32.5

⌬Hv

81 24.56

⌬Hs

400 K

23.1 57.5

76.7 728

32.1 390.4 44.8

10.57 10.4 12.05 5.67 6.19 20.9 48.58 22.6 15.3 32.6

29.96 34.7 25.1 47.6 30.6

30.9

99.9 115 124.3 214 115

21.4 79.5

70

154.7

200

800 K

1000 K

68.4(g) 67.1

75.0 72.6

78.2 75.8

79.8

38.9 74.3 130.2(g)

45.4 101.3 187.6

52.3 121.7 227.4

58.4 136.4 254.4

250.0(lq)

351.6(g)

417.2

460.4

26.3 126.9 77.9 120.1

35.2 169.4 98.1(c) 162.8

40.5 44.3 197.2 216.6 129.7(lq) 129.7 194.6 214.2

36.7(g)

72.6 113.0

225.1 209.6

8.54 74.1 113.4 29.1 32 28.05 0.432 36 29.3 6.7 41.8

600 K

298.3

235

37.3

37.6

37.8

78.0 123.2

80.1 127.3

81.2 129.3

27.1(c)

29.7(lq)

29.7

29.7

79.8

86.3

92.7

104.6

43.8 55.5 108.3

45.6 56.2 123.8

47.3 57.0 139.2

49.1 57.7 154.7

26.9 125.0 202.0 78.0

30.0 144.9 243.0 80.5

33.8 157.2 267.7 83.5

39.7 176.2 287.8 88.6

75.6

78.2

80.9

85.8

308.9

441

73.9

78.5

83.9

90.1

179.4

243

79.2 143.3 131.3 122.2 173.7 46.6 98.4 255.1 49.2

83.1 163.3 144.9 140.8 210.5 50.5 107.4 295.6 51.5

87.1 176.8 153.5 159.2 243.4 52.4

91.0 188.3 150.6

331.3 53.0

365.7 54.1

53.7

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THERMODYNAMIC PROPERTIES

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

top of rh base of rh cap height base of text

Cp ⌬Hm

Substance CaSiO3, ⌬Ht ⫽ 7.1 Ca2SiO4, ⌬Ht ⫽ 4.44675 ⌬Ht ⫽ 3.261420 3CaO · SiO2 CaSO4 CaSO4 · 1⁄2H2O CaSO4 · 2H2O CaTiO3, ⌬Ht ⫽ 2.301257 Ca(VO2)2 CaWO4 Carbon C graphite (CN)2 cyanogen CNBr CNCl CNI CO, ⌬Ht ⫽ 0.632⫺211.6 CO2 C2O3 COCl2 COF2 COS CS2 Cerium Ce, ⌬Ht ⫽ 3.01730 CeCl3 CeI3 CeO2 Cesium Cs CsBr CsCl, ⌬Ht ⫽ 3.77470 CsF CsI CsIO3 CsOH, ⌬Ht ⫽ 1.30137 ⌬Ht ⫽ 6.1220 Cs2SO4, ⌬Ht ⫽ 4.3667 Chlorine Cl2 ClF ClF3 ClF5 ClO ClO2 ClO3F Cl2O Cl2O7 Chromium Cr, ⌬Ht ⫽ 0.000838.5 1190

⌬Hv

⌬Hs

56.1

28.0

117 8.1

23.3

19.7 45.4

11.4 59.4 0.837 9.02 5.40 5.74 7.73 4.40 5.46 54.4 51.9

2.09 23.6 15.9 21.7 23.9 13.0 4.56

6.04 15.8 26.943.5 24.4 16.1 18.6 26.7 398 170.1

63.9 151 115.1 115.5 150.2

7.61

3.83

21.0

27.5 419 326

76.6

120

35.7 6.406

25.2

20.41 24 27.5 22.9

600 K

800 K

1000 K

100.4 146.4

113.0 162.8

119.2 179.2

123.8 184.0

196.4 109.7 147.4 260.7 112.3 182.9 127.6

218.4 129.5 167.2 280.3 123.1 206.7 140.2

230.8 149.2 186.9 300.0 127.7 230.5 147.3

240.4 169.0 206.7 319.8 130.4 254.4 152.8

12.0 61.9(g) 50.19(g) 48.7 50.8 29.3 41.3 75.0 63.9 54.8 45.9 49.7

16.6 68.2 53.7 52.8 53.7 30.4 47.3 85.5 71.1 64.9 51.3 54.6

19.7 72.9 56.2 55.7 55.8 31.9 51.4 92.7 75.0 70.8 54.7 57.4

21.7 76.4 58.1 57.7 57.4 33.2 54.3 97.7 77.4 74.4 57.0 59.3

30.6

30.8

32.1

33.8

66.9

69.0

71.1

73.2

31.5 52.9 54.7 53.8 51.9

31.0 55.0 59.1 57.4 57.8(c)

30.9(lq) 57.2(c) 63.7(c) 60.9(c) 65.5(lq)

20.8(g) 77.4(lq) 77.4(lq) 74.1(lq) 67.8

74.4(c)

81.6(lq)

81.6

81.6

76.5

112.1

132.2

163.2

194.2

17.65

35.3 33.8 70.6(g) 110.0 33.2 46.1 75.9 51.4

36.6 35.6 76.8 121.6 35.3 51.4 89.2 54.7

37.1 36.5 79.4 126.3 36.3 54.2 96.1 56.2

37.4 37.0 80.7 128.6 36.9 55.8 100.0 56.9

27.7

29.4

31.9

30 19.33 25.9 34.69 339.5

400 K

397

25.2

short standard long

DEAN #37261

LEFT

(McGHP)

6.128

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

cap height base of text

Cp Substance CrCl2 CrCl3 Cr(CO)6 CrN, ⌬Hdec ⫽ 112 CrO2Cl2 CrO2F2 CrO3 Cr2O3 Cr2(SO4)3 Cobalt Co, ⌬Ht ⫽ 0.452427 CoCl2 CoF2 CoF3 CoO Co3O4 CoSO4, ⌬Ht ⫽ 2.1691 Copper Cu CuBr, ⌬Ht ⫽ 5.86380 ⌬Ht ⫽ 2.9465 CuCl CuCl2, ⌬Ht ⫽ 0.700402 ⌬Ht ⫽ 15.001598 CuCN CuF CuF2 CuI CuO Cu2O CuS Cu2S, ⌬Ht ⫽ 3.85103 ⌬Ht ⫽ 0.84350 Cu2Se, ⌬Ht ⫽ 4.85110 CuSO4 Dysprosium Dy Erbium Er Europium Eu Fluorine F2, ⌬Ht ⫽ 0.728⫺227.6 FNO3 Gadolinium Gd Gd2O3 Gallium Ga GaBr3

⌬Hm 32.2

⌬Hv

⌬Hs

196.7 237.7 72.0 49.1

23.4 15.77 129.7

400 K

600 K

800 K

1000 K

72.6 93.1 233.9 50.4

77.0 99.0

81.5 104.9

85.9 110.7

51.7

53.0

63.9 112.7 316.9

72.5 120.5 345.2

76.7 124.3 373.5

78.8 127.0 401.8

26.5 81.7 75.7 97 52.9 143 119

29.7 84.6 80.8 100 54.3 163 141

32.4 86.8 82.9 102 54.8 185 152

37.0 88.2 84.2 104 56.0 210 158

35.1 34.3

16.2 45 59

377 146 202

424 219 315

13.26 9.6

300.4

337.7

25.3 56.5

26.5 59.8(c)

27.4 66.9(lq)

10.2 20.4

54

241.8

56.9 76.3

61.5(c) 80.2(c)

66.9(lq) 66.9 82.4(lq) 100.0 78.0

55.5 72.4 55.4 46.8 67.6 48.8 97.3

66.7 59.6 81.9 57.8 50.8 73.3 51.0 97.3

73.1

268 261

87.0 60.2 53.2 77.6 53.2 85.0

90.4 66.9 55.0 81.5 55.4 85.0

90.9 114.9

91.7 136.3

92.5 147.7

93.4 153.8

33.0 75.1

35.2 87.8

36.3 94.8

37.1 98.9

36.6 113.4

35.5 120.1

34.5 124.4

33.5 127.9

26.7

26.6

26.6

12 55 10.9 11.8 64.8

156

10.9

11.06

280

290.4

19.90

280

317.2

9.21

176

178

0.510

6.62

10.05

301.3

5.59 12.1

254 38.9

27.1(lq)

28.7 66.9

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.129

THERMODYNAMIC PROPERTIES

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance GaCl3 GaI3 Ga2O3 GaSb Germanium Ge, ⌬Ht ⫽ 37.03938.3 GeBr4 GeCl4 GeH4 Ge2H6 Ge3H8 GeO2 Gold Au AuSn Hafnium Hf, ⌬Ht ⫽ 5.91750 HfCl4 HfO2, ⌬Ht ⫽ 10.51700 Helium He Holmium Ho Hydrogen H2 1 2 HH 2 H2 HBO2 H3BO3 HBr HCl, ⌬Ht ⫽ 1.188⫺174.77 2 HCl HClO HCN HF 2 HF H2F2 dimer HFO HI HNCO isocyanic acid HNCS isothiocyanic acid HNO2 cis trans HNO3 HN3 H2O 1 2 H HO 2 H2O H2O2 2 H2O2

⌬Hm

⌬Hv

11.13 12.9 100 25.1

23.9 56.5

36.94

334 41.4 27.9 14.1 25.1 32.2

⌬Hs

43.9 12.55 25.6 27.2 75 104.6 0.0138 16.8 0.117

14.3 22.3 2.406 1.992

324

571

618.4 99.6

0.0829

242.1 12.7 9.1

8.406 4.58

25.22

2.87

19.77

17.4

10.47

39.46 30.5 40.66

39.1

6.009

12.50 12.68

44.0

51.63 52.4

800 K

1000 K

112.5

133.5

24.3

25.4

26.2

26.9

100.7

104.6

106.1

106.8

61.39

69.1

72.4

75.0

25.8 54.1

26.8 63.3(c)

27.8 60.6(lq)

28.8

26.7 125.4 67.7

280

0.904

600 K

91.4

20.79

71

17.61 16.14

400 K

28.6 105.8 73.9 20.79

30.3 106.7 77.3

31.9 107.1 79.9

20.79

20.79

317

29.2 29.2 29.2 61.5(c)

29.3 29.4 29.6

29.6 29.9 30.5

30.2 30.7 31.6

29.2 19.2 29.4 40.0 39.4 29.1 29.2 49.7 38.6 29.3 50.6 53.2 51.4 52.1 63.1

29.8 29.2 30.6 44.0 44.2 29.2 29.5 56.5 42.8 30.3 58.3 61.0 59.9 60.3 76.8

31.1 29.6 32.1 46.6 47.9 29.5 30.5 61.0 45.7 31.8 63.5 65.9 65.4 65.6 85.0

32.3 31.6 33.5 48.5 51.0 30.2 31.6 64.4 47.9 33.1 67.5 69.3 69.2 69.3 90.4

34.3(g) 34.8 35.6 48.5

36.4 37.5 38.8 55.7

38.8 40.4 42.2 59.8

41.4 43.3 45.4 66.7

short standard long

DEAN #37261

LEFT

(McGHP)

6.130

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

cap height base of text

Cp Substance HPH2O2 H3PO3 H3PO4 H2S, ⌬Ht ⫽ 1.531⫺169.61 H2S2 H2Se HSO3F H2SO4 H2SO4 · H2O H2SO4 · 2H2O H2SO4 · 3H2O H2SO4 · 4H2O H2Te Indium In InBr InBr3 InCl InCl3 InF3 InI InI3 In2O3 InSb Iodine I2 ICl IF IF5 IF7 Iridium Ir IrF6 IrO2 Iron Fe, ⌬Ht ⫽ 0.90911 ⌬Ht ⫽ 0.8371392 FeBr2 FeBr3, ⌬Ht ⫽ 0.418377 Fe2C, ⌬Ht ⫽ 0.75190 FeCl2 FeCl3 FeCO3 Fe(CO)5 FeCr2O4 FeF2 FeF3 FeI2, ⌬Ht ⫽ 0.8377 Fe3N FeO

⌬Hm 9.67 12.84 13.4 23.8

10.71 19.46 18.24 24.0 30.64

⌬Hv

⌬Hs

18.67 33.8 19.7

14.1

50.2

400 K

600 K

800 K

175.7 38.9

236.0 42.5

296.2 45.8

87.5 158.2 228.5 294.6 347.8 410.3

102.6 111.0 197.0(lq) 125.9(g)

1000 K

365.5

116.3 132.7

19.2 3.28 15 26 21.3 27 64 17.3 18.5 105 25.5

231.8 92

150.66 11.60

41.6

243.1

28.5(c)

13.81

231.8 36

340

50.2 50.2 51.5 43.01 43.1

26.3 43.76

13.23

33.72

62.4 52.9

79.6(lq) 98.3(lq) 35.1 476.1(g) 152.0(g)

243.1

415.5

207.5

51.9

224.4

45

104.6

24.06

30.1

30.1

37.6(g) 90.0 36.6 516.7 167.6

37.9 81.6 37.3 533.0 173.9

38.1 73.2 37.7 541.4 177.0

28.5(c)

30.1(lq)

30.1

30.1

63.8

76.5

89.2

102.0

27.4

32.1

38.0

54.4

90.8

41.3

41.12 8.40

30.1(lq)

316 274 192

83.0 115.7 79.7 106.7(c) 93.5 189.0 152.0 72.0 96.4 83.9 72.6 51.8

87.0 114.7 83.1 133.9(lq) 115.9 209.8 167.7 77.1 96.8 84.4 77.7 54.9

91.4 117.2 85.5 82.3(g) 138.3 223.1 175.9 80.3 99.3 110.9 82.8 57.3

95.9 119.8 101.2 81.5 232.2 182.2 82.1 101.8 113.0(lq) 87.9 59.4

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.131

THERMODYNAMIC PROPERTIES

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

top of rh base of rh cap height base of text

Cp ⌬Hm

Substance Fe2O3, ⌬Ht ⫽ 0.67 Fe3O4 Fe(OH)2 Fe(OH)3 FeS, ⌬Ht ⫽ 0.40138 ⌬Ht ⫽ 0.095325 FeS2 marcasite pyrite FeSiO3 Fe2SiO4 FeSO4 Fe2(SO4)3 FeTiO3 ilminite Krypton Kr Lanthanum La, ⌬Ht ⫽ 2.85868 LaCl3 La2O3 Lead Pb Pb(BO2)2 PbB4O7 PbBr2 Pb(CH3)4 Pb(C2H5)4 PbCl2 PbCO3 PbF2, ⌬Ht ⫽ 1.46310 PbI2 PbMoO4 PbO, ⌬Ht ⫽ 0.17488 PbO2 Pb3O4 PbS PbSiO3 Pb2SiO4 PbSO4, ⌬Ht ⫽ 17.2866 PbSO4 · PbO Lithium Li Li2AlF6, ⌬Ht ⫽ 9.5562 LiAlO2 LiBH4 LiBeF3 Li2BeF4 LiBO2 Li2B4O7 LiBr LiCl

⌬Hv

⌬Hs

677

138.1 243.5 31.5

92

90.8 1.37

111.4

122.0

402.1 192.1

4.77

179.5

195.2

16.44 10.86 8.80 21.9

133

173

127

185.3

14.7 23.4

157 104

172

25.5

207

18.8 26.0 51.0 40.2

230

27.2 44.0 33.8 121 17.6 19.9

600 K

800 K

1000 K

120.1 171.1 102.1 118.0 89.2

141.2 212.5 111.3 140.6 62.0

158.2 252.9 118.9 154.8 58.6

150.6

69.2 68.9 100.8 150.9 116.7 307.0 128.1

74.6 74.3 114.3 168.5 138.0 363.3 132.8

78.7 78.3 124.5 179.7 149.4 393.3

82.8 82.5 133.9 189.1

28.5 105.8 117.3

29.8 110.1 124.7

31.2 114.3 128.9

32.5 118.7 132.3

27.7 129.7 207 81.3

29.4 162.3 265 88.8

30.0

29.4

305 330 112.1(lq) 112.1

80.1 99.7 76.1 78.9 135.3 50.4 67.6 173.1 50.5 101.5 152.0 108.7 157.3

85.9 123.6 82.5 83.7(c) 148.9 55.4

111.5(lq) 111.5 147.6 89.1 95.6 108.6(lq) 108.6 159.0 168.2 55.0 57.8

190.8 52.4 113.5 173.3 128.6 182.5

199.2 54.3 125.6 184.2 152.4 211.7

56.2 138.4 189.1 177.3 242.0

29.5(lq) 28.9 262.8 290.8 92.7 98.2

28.8 318.6 102.0

129.7(c) 180.2(c) 85.1 241.1 56.1 55.6

159.0 232.1 108.3 300.2 65.3(lq)

123.4 164.9 59.0

409.2

9.08

6.20 43.1

3.00 110.5 87

400 K

147.1

265 107.1

159.3

27.6(c) 236.4 81.5 91.0 104.6 150.5 81.1 197.6 51.3 51.0

159.0(lq) 232.1(lq) 96.9 274.4 64.5(c) 65.8

short standard long

DEAN #37261

LEFT

(McGHP)

6.132

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

cap height base of text

Cp Substance LiClO4 Li2CO3, ⌬Ht ⫽ 0.561350 ⌬Ht ⫽ 2.238410 LiF LiH LiI LiIO3, ⌬Ht ⫽ 2.22260 Li3N LiNO3 Li2O Li2O2 LiOH Li2SiO3 Li2Si2O5, ⌬Ht ⫽ 0.941936 Li2SO4, ⌬Ht ⫽ 28.5575 Li2TiO3, ⌬Ht ⫽ 11.511212 Lutetium Lu Magnesium Mg MgAl2O4 MgBr2 MgCl2 MgCO3 MgF2 MgH2 MgI2 Mg3N2, ⌬Ht ⫽ 0.46550 ⌬Ht ⫽ 0.92788 Mg(NO3)2 MgO Mg(OH)2 Mg3(PO4)2 MgS Mg2Si MgSiO3, ⌬Ht ⫽ 0.67630 ⌬Ht ⫽ 1.63985 Mg2SiO4 MgSO4 MgTiO3 Mg2TiO4 MgWO4 Manganese Mn, ⌬Ht ⫽ 2.23727 ⌬Ht ⫽ 2.121101 ⌬Ht ⫽ 1.881137 MnBr2 Mn3C, ⌬Ht ⫽ 14.941037 MnCl2 Mn2(CO)10

⌬Hm

⌬Hv

⌬Hs

29 41 27.09 22.6 14.6

400 K 130.0(c) 112.2

146.8

276.1 231.3

24.9 58.6 250.6

600 K

800 K

161.0(lq) 161 149.4 159.0

1000 K 161

46.5 34.8

51.6 46.4

55.7 57.3

59.6

87.1

106.4

124.4

141.0

64.0 82.7(c) 58.0 118.8 174.9 139.2 127.4

73.8 80.2(g) 68.2(c) 134.3 205.7 168.5 141.5

80.6 81.4 87.1(lq) 144.4 222.6 196.1 149.0

86.2 82.1 87.1 152.3 235.4 223.4 153.9

28.2 157.9 81.4 79.9 109.0 75.3

30.5 169.5 84.5 82.5 122.3 78.6 96.3(c) 123.8

20.88 28.0 53.8 7.50 110.7

187.9

(22)

414

8.48 192 39.3 43.1 59 58.5 14 26

128

147

149 156.2

222 249.2

274.1

399.5

26.1 138.0 77.3 75.7 89.9 68.5

206 107.6

78.4 113.8

83.0 119.9

168.5 42.6 91.7 240.2

225.5 47.4

49.7

51.2

282.2

320.6

351.5

73.8 94.2

79.8 107.0

83.9 115.8

87.4 120.3

137.6 110.0 105.2 146 123.4

156.4 127.6 118.5 164 137.0

167.1 140.5 125.4 175 146.1

174.6 151.7 129.9 184 154.8 37.5

77 121 63 85.8 71

14.6

12.9

221

28.5

31.9

34.9

33

113

30.7

149.0

77.8 104.4 77.2

82.8 115.0 81.8

87.7 121.7 85.1

62.8

178.7

131.8 80.5 100.4(lq)

127.4 96.2(lq)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.133

THERMODYNAMIC PROPERTIES

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance MnF2 MnI2 MnO MnO2 Mn2O3 Mn3O4, ⌬Ht ⫽ 20.791172 MnS MnSiO3 MnSO4 MnTiO3 Mercury Hg HgBr2 Hg2Br2 HgCl2 Hg2Cl2 HgF2 Hg2F2 HgI2, ⌬Ht ⫽ 2.52129 Hg2I2 HgO HgS, ⌬Ht ⫽ 4.2386 Molybdenum Mo MoBr3 MoCl4 MoCl5 Mo(CO)6 MoF6, ⌬Ht ⫽ 8.17⫺9.65 MoO2 MoO3 MoS2 Mo2S3 Neodymium Nd, ⌬Ht ⫽ 2.98862 Nd2O3 Neon Ne Neptunium Np, ⌬Ht ⫽ 8.37280 Nickel Ni NiCl2 Ni(CO)4 NiF2 NiO NiS, ⌬Ht ⫽ 6.4379 Ni3S2, ⌬Ht ⫽ 56.2556 NiS2 NiSO4

⌬Hm

⌬Hv

⌬Hs

23.0 42 54.4

26.4 66.9

2.29 17.9

59.1 58.9

19.41

58.9

23.0

92

18.9 27.8

59.2

37.48 17 18.8 4.33 48

617 61.5 62.8 72.5 27.2

61.4

664

69.9 28.0

138

130 7.14

0.335 3.20 17.48 71.2 13.8

30.1 19.7 65.7

289

400 K

600 K

800 K 80.7 89.0 52.4 75.1 129.4 179.7 53.7 119.5 147.7 125.7

1000 K

70.6 78.1 47.5 63.4 109.0 157.3 50.7 100.9 119.0 111.7

75.7 83.6 50.3 71.1 120.8 169.5 52.2 113.1 136.7 121.2

85.9 108.8 54.2

27.4 78.3 109.6 77.0(c) 106.0 77.0 104.7 82.0(c) 110.4(c) 48.3 48.0

27.1(lq) 20.8(g) 102.1(lq) 102.1 115.6 102.9(lq) 112.1 81.2 85.4(c) 111.7 116.9 84.1(lq) 62.2(g) 136.4(lq) 54.1 51.0 54.1

25.1 106.9 135.0(c) 167.4(c)

26.5 27.4 109.8 112.7 146.4(lq) 175.7(lq) 175.7

175.7

133.1 63.5 83.1 68.9 117.5

145.3 71.2 91.8 73.6 127.4

150.4 76.5 100.0 76.2 135.2

153.0 81.4 109.0 78.2 142.3

28.2 120.3

32.1 130.0

36.9 137.7

42.0 144.4

30.0 79.9 173.2 78.5 51.8 13.2 139.9 70.0 150.8

31.0 80.9 182.1 82.6 53.6 13.7 150.7 81.0 159.2

32.2

137.2 189.3 55.2 124.2 128.8 20.8 102.1

102.9(lq) 62.2

28.4

1.71 336

34.8

377.5 231.0 29.3

28.5 76.3 160.4(g) 76.4 52.2 12.1 127.1 72.8 142.6

188.6 55.2 15.1 188.6 85.2 167.4

short standard long

DEAN #37261

LEFT

(McGHP)

6.134

INTERACTIVE

top of rh base of rh

SECTION 6

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

cap height base of text

Cp Substance NiWO4 Niobium Nb NbBr5 NbCl5 NbF5 NbI5 NbN, ⌬Ht ⫽ 4.21370 NbO NbO2, ⌬Ht ⫽ 3.42817 Nb2O5 Nitrogen N2, ⌬Ht ⫽ 0.230⫺237.53 NF3 N2F2 cis trans N2F4 NH3 (see Ammonium) N2H4 NO NOCl NOF NOF3 NO2 NO2Cl NO2F NO3 N2O N2O4 N2O5 NSF Osmium Os OsF6 OsO4 Oxygen O2, ⌬Ht ⫽ 0.092⫺249.49 ⌬Ht ⫽ 0.745⫺229.38 O3 OF2 O2F2 Palladium Pd PdCl2 PdO Phosphorus P P4, ⌬Ht ⫽ 0.521⫺77.8 PBr3 PClF2

⌬Hm

30 24.0 38.3 12.2 37.7 46.0 85 92 104.3 0.720 15.4 14.2

12.66 2.30

⌬Hv

689.9 50.2 52.7 52.3 58.6

⌬Hs

726 112.5

618 598.0

5.577 11.6 91.6 87.9 13.3 41.8 13.83 25.8 19.3

44.7

16.53 38.12 62.3

600 K

800 K

1000 K

138.9

144.6

150.3

155.9

25.4 147.9(c) 170.7(c) 43.5(lq) 182.0(c) 45.4 44.0 63.5 145.0

26.3 27.2 147.9(lq) 127.9(g) 129.8

28.0 130.7

49.9 47.2 71.7 160.7

51.6 49.5 70.5 170.0

53.2 51.5 87.5 175.5

30.1 71.4 68.3 68.9

31.4 76.0 73.6 73.8

32.7 78.4 76.6 76.7

77.6 31.2 50.7 48.9 90.9 46.4 68.1 66.4 67.4 48.4 104.0 128.4

88.2 32.8 53.2 51.7 97.0 50.4 73.1 71.9 73.3 52.2 113.4 137.0

96.4 34.0 54.9 53.5 100.5 53.0 76.1 75.3 76.5 54.9 119.2 141.4

25.1

25.9

26.7

27.4

30.11

32.09

33.74

34.88

43.74 64.3

49.86 72.4

53.15 76.4

55.02 78.6

26.5

27.7

28.8

30.0

37.6

49.5

61.3

14.2 73.3(g) 78.9

78.4 81.2

80.4 82.0

29.2 61.9 58.2 60.2

25.7 18.0 6.54 14.65

400 K

61.7(g) 29.9 47.1 44.6 78.7 40.5 59.6 57.0 55.9 42.7 88.5 110.9

22.2 57.85 9.8 0.444

738 28.62 39.54 6.820

8.204

10.84 11.09 19.1 16.74 40.1

0.659

362

0.66 56.5 38.8 17.6

12.4 58.9

81.4 82.4

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.135

THERMODYNAMIC PROPERTIES

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

top of rh base of rh cap height base of text

Cp Substance PClF3 PCl2F PCl3 PCl5 PF3 PF5 PH3 P2H4 PI3 P4O6 P4O10 POBr3 POCl3 POClF2 POCl2F POF3 PSCl3 PSF3 P4S3 Platinum Pt PtS PtS2 Plutonium Pu, ⌬Ht ⫽ 13.4122 ⌬Ht ⫽ 2.9206 ⌬Ht ⫽ 3.3319 ⌬Ht ⫽ 66.9480 PuBr3 PuCl3 PuF3 PuF4 PuF6 PuI3 PuO2 Polonium Po Potassium K KAlCl4 K3AlCl6 K3AlF6 KBF4, ⌬Ht ⫽ 14.06283 KBH4 KBO2 K2B4O7 KBr KCl KClO4, ⌬Ht ⫽ 13.77299.6 KCN, ⌬Ht ⫽ 1.167⫺104.9

⌬Hm

7.10

1.130

14.06 27.2 38 13.1

⌬Hv 17.6 24.9 30.5

9.2

19.58 59.8

55.2 63.6 59.8 65.3 17.6 50.2

32.1 64.9

76.0(g) 120.1(g) 66.3(g) 99.2(g) 41.8

79.7 126.8 74.0 114.7 50.9

81.2 129.5 77.6 121.9 58.5

81.9 130.7 79.5 125.6 64.3

172.1 260.3

200.8 336.0(c)

213.5

220.0

92.0(g) 79.3 87.7 79.1 96.5 84.5 184.1

99.1 91.6 96.6 91.2 102.4 95.3 184.1(lq)

102.5 97.7 100.9 97.4 104.8 100.3 155.0(g)

108.5 101.1 103.2 100.9 105.9 102.9 155.0

106.0

15.06

2.82

400 K

16.5 17.2 14.60 28.8 43.9 43.43

34.3 25.4 30.96 23.22

22.17

⌬Hs

469

38.6

21.1

545

333.5

236.4 241.0

29.9

600 K

800 K

1000 K

26.4 51.4 69.9

27.5 53.8 75.9

28.5 56.2 8l.9

29.6 58.6 87.9

39.5

46.9

40.6

40.6

30.1 183.2 279.5 269.4 142.1 106.0 89.8 250.5 56.4 55.9 165.3 66.4

29.8 196.6 295.8 286.8 150.9 118.4 98.5 271.1 60.4 59.2

30.7 202.1

292.5 304.6 374.9 299.6 48.5

559.8 102.91 2.321

76.90

17.7 31 104 25.5 26.53

238.9 149.2 124.3

14.6

157.1

88.8

31.5(lq) 165.5 259.2 244.5 130.8 100.9 76.7 206.3 53.8 53.0 138.5 66.3

66.5(c)

302.0 167.2

283.3 68.0 64.0 66.5(lq)

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SECTION 6

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

cap height base of text

Cp Substance K2CO3 K2CrO4 K2Cr2O7 KF KH KHF2, ⌬Ht ⫽ 11.22196.7 KI KNO3, ⌬Ht ⫽ 5.10128 K2O, ⌬Ht ⫽ 6.20372 KO2, ⌬Ht ⫽ 0.302⫺79.7 ⌬Ht ⫽ 0.157⫺42.3 K2O2 KOH, ⌬Ht ⫽ 6.4243 KPO3 K3PO4 K2P2O7 KReO4 K2S K2SiO3 K2SO4, ⌬Ht ⫽ 8.45584 K2WO4 K2ZrCl6 Praseodymium Pr Promethium Pm Protactinium Pa PaCl3 Radium Ra Radon Rn Rhenium Re ReF5 ReF6 ReF7 ReO2 ReO3 Re2O7 ReOCl4 ReOF4 ReOF5 Rhodium Rh Rh2O3 Rubidium Rb RbBr

⌬Hm 27.6 29.0 36.7 27.2 6.62 24.0 10.1

8.60 8.8 37.2 58.6 85.4 16.15 50 34.39 19.5 23.0

⌬Hv

⌬Hs

141.8

231.8

190.9

202.4

142.7

77.3

192

82.5

6.89

331

356

7.13

289

328

12.34 92.9 8.5 3.247 60.43 4.6 7.5 21.8 64.2 13.5

400 K

600 K

800 K 170.0

1000 K

128.1

150.7

51.0 44.1 86.1(c) 53.9 108.4 79.1 83.9

54.3 57.4 51.9 104.6(lq) 57.3 62.6(c) 120.5 100.0 100.0 90.2

107 72.5

121 79.0(c)

87.7 135.6 147.6

157.7 172.5

170.7 199.6

179.1 226.1

26.0

26.9

28.0

29.1

26.0 109.9

28.0 121.4

30.0 133.0

32.0 144.5

31.7 52.8

30.9 54.9

83.0(lq)

189.0

61.2

72.4(lq) 100.0

83.0

481 61.3 113 18.10 704 58.1 28.7 38.3

779

274.6 208.4 74.1 45.6 61.0 32.0

26.59

494

2.19 15.5

75.77 154.8

37.4 556

30.7 57.1(c)

66.9(lq)

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THERMODYNAMIC PROPERTIES

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

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Cp Substance RbCl RbClO4, ⌬Ht ⫽ 12.59284 RbF RbI RbNO3 RbOH Ruthenium Run, ⌬Ht ⫽ 0.131035 ⌬Ht ⫽ 0.961500 Samarium Sm, ⌬Ht ⫽ 3.11917 Sm2O3, ⌬Ht ⫽ 1.05922 Scandium Sc ScCl3 Sc2O3 Selenium Se, ⌬Ht ⫽ 0.75150 SeF4 SeF6 SeO2 SeOCl2 Silicon Si SiBr4 SiC beta SiCl4 SiClF3 SiCl2F2 SiF4 SiH4 Si2H6 Si3H8 SiH3Br SiH2Br2 SiHBr3 SiH3Cl SiH2Cl2 SiHCl3 SiH3F SiH2F2 SiHF3 SiI4 Si3N4 SiO2 cristobalite SiO2 quartz ⌬Ht ⫽ 0.73574 ⌬Ht ⫽ 2.0806 SiOF2 SiS2

⌬Hm

⌬Hv

⌬Hs

400 K

600 K

800 K

1000 K

18.4

165.7

52.3

54.3

56.4(c)

64.0(lq)

17.3 12.5 5.61 6.78

177.8 150.6

51.9

57.9 55.1

64.9 57.3(c)

72.3 66.9(lq)

38.59

591.6

24.5

25.7

27.0

28.2

33.3 125.2

39.1 135.3

44.3 141.4

49.3 146.3

96.7 106.4

102.7 111.1

108.7 115.8

114.6 120.5

8.62

14.1

6.69

165

207

332.7

376

95.48 47.2

8.4 4.23

28.1(c) 26.8

359 37.9

7.60

28.7 18.7 21.2

0.67

12.1 21.2 28.5 24.4 31 34.8 21 25.2 26.6 18.8 16.3 16.2 56.9

450

29.7

25.7

8.51 7.7

20.9

35.1

127.9

141.3

147.1

150.7

22.3 146.4(lq) 34.1 96.9(g) 88.3

24.5 104.9(g) 41.8 102.6 97.5

25.7 106.2 45.9 104.8 101.7

26.5 106.2 48.4 106.0 103.8

94.5 42.7

50.21

19.7

35.2(lq)

24.2 25.7

79

600

83.1 51.5

94.1 65.9

99.4 76.7

102.3 84.5

60.7 71.5 83.7 57.2

74.0 82.9 92.5 71.8

83.1 90.0 97.2 81.7

89.4 94.6 100.2 88.3

106.9 145.8

107.3 158.2

164.0(lq) 110.7

106.0(g) 129.7

53.5

64.4

76.2

68.94

61.3 78.6

70.4 81.7

75.0 83.4

77.6 85.4

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SECTION 6

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

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Cp Substance Silver Ag AgBr AgCl Ag2CO3 AgF AgI, ⌬Ht ⫽ 6.15147 AgNO3, ⌬Ht ⫽ 2.5160 Ag2O Ag2S, ⌬Ht ⫽ 5.86176 ⌬Ht ⫽ 5.86586 Sodium Na NaAlCl4 Na3AlCl6 Na3AlF6, ⌬Ht ⫽ 8.37565 ⌬Ht ⫽ 0.42880 NaAlO2, ⌬Ht ⫽ 1.297467 NaBH4, ⌬Ht ⫽ 0.999⫺83.3 NaBO2 Na2B4O7 NaBr NaBrO3 NaCl NaClO3 NaClO4, ⌬Ht ⫽ 13.98308 NaCN Na2CO3, ⌬Ht ⫽ 0.690450 NaF NaH NaI NaIO3, ⌬Ht ⫽ 35.1422 NaNO3 NaO2, ⌬Ht ⫽ 1.464⫺76.7 ⌬Ht ⫽ 1.548⫺49.9 Na2O, ⌬Ht ⫽ 1.76750.1 ⌬Ht ⫽ 11.92970.1 Na2O2, ⌬Ht ⫽ 5.73512 NaOH, ⌬Ht ⫽ 72299.6 Na2S Na2S2 Na2SiO3 Na2Si2O5, ⌬Ht ⫽ 0.42678 Na2SO4, ⌬Ht ⫽ 10.91241 Na2TiO3 Na2WO4, ⌬Ht ⫽ 30.85587.7 ⌬Ht ⫽ 4.113588.9 Strontium Sr, ⌬Ht ⫽ 0.84547 SrBr2, ⌬Ht ⫽ 12.2645

⌬Hm

⌬Hv

11.95 9.12 13.2

258 198 199

16.7 9.41 11.5

179.1 143.9

⌬Hs

25.7 59.0 56.9 54.1(c) 64.7 112.5 73.0 86.6

14.1

2.60

97.42

107.5

107.28

36.2 76.9 26.11 28.11 28.16 22.1 8.79 29.64 33.35

400 K

239.7

322.2

160.7

217.5

148.1

172.8

176.1

284.9

23.60

600 K

800 K

1000 K

26.8 71.8(c) 54.4 122.6 58.4 56.5 128.0

28.4 62.3(lq) 54.4

30.0 62.3 54.4

56.5

58.6(lq)

90.5

90.5

90.5

31.5(lq) 164.8(c) 254.4 234.6

29.3

29.9

29.0

273.0 261.8

196.8

282.8

83.4 94.6 75.4 221.7 53.5

94.3 108.6 88.6 268.6 56.1

98.7

102.3

52.3

55.5

59.3

72.5

68.8 163.3 52.7 50.7 56.2

69.0 153.3 55.7

179.8 59.5

76.3

84.5

92.6

75.8

85.7

91.3

136.0(c) 68.7 125.1 49.6 42.5 53.8

97.2 103.2 444.9(lq) 58.6 61.1

58.5(c)

64.9(lq)

15

47.7

6.60 19.3

175.3

228.2

51.8 35.6 23.6 70.3 23.80

7.43 10.1

136.9 194.1

164.0 310

97.7 64.9(c) 20.1 104.3 127.8 183.4 145.1

108.4 86.1(lq) 20.9 115.4(c) 147.1 217.6 175.3

113.6 84.9 21.5 124.7(lq) 159.7 235.2 187.3

155.3

178.2

198.7

27.8 79.0

29.8 82.7

31.9 87.6(c)

94.9

83.7 22.0 124.7 169.4 292.9 200.3

34.1 116.4(lq)

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TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

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Cp ⌬Hm

Substance SrCl2, ⌬Ht ⫽ 6.0 SrCO3, ⌬Ht ⫽ 19.7924 SrF2, ⌬Ht ⫽ 0.041148 ⌬Ht ⫽ 0.041211 SrI2 SrH2 SrMoO4 SrO SrO2 Sr(OH)2 SrS SrSO4 Sulfur S monoclinic ⌬Ht ⫽ 0.40095.2 S8 SCl2 S2Cl2 SF4 SF6 S2F10 SO2 SO3 SOCl2 SOF2 SO2Cl2 SO2ClF SO2F2 Tantalum Ta TaB2 TaBr5 TaC Ta2C TaCl5 TaF5 TaI5 TaN TaO2 Ta2O5 Technetium Tc TcF6 TcO3F Tellurium Te TeCl4 TeF4 TeF6 Te2F10 727

⌬Hv

⌬Hs

17.5 40 28.5

248.1

356

320

19.67 23

189.7

451.0

83.7 107.1 79.8

286.6

80.7

86.3

131.5 48.5 81.3 88.5 50.2 113.5

23 63 36 1.727

45

5.02

32.4 36.0 26.4 17.1 24.94 40.7 31.7 21.8 31.38

62.2

9.0 22.92 43.14 31 30.1

20.0 36.57 83.7 45.6 105

732.8

41.6 18.8 41.8 67

54.8 56.9 64.9

778

62.3

94.1

120 33.29 4.72 22.5

585.2 31.1 39.5

17.49 18.8

114.1 77 34.3

23.2 167.1 53.6 124.3(lq) 87.5 116.4 211.4 43.43 57.7 71.3 64.3 85.2 81.1 76.5 25.8 57.6 168.2 41.7 66.7 148.(c) 182.0(lq) 164.6 45.4 47.7 147.5 25.1

28.2 39.5

600 K

78.9 95.1 74.7

81

7.40 8.60

400 K

145.4 52.0 85.0 115.0(c) 53.2 124.6 23.3(lq) 177.9 56.0 80.8(g) 97.3 136.1 246.4 48.9 67.3 76.4 72.4 94.5 92.1 89.3

800 K 90.8 116.1 81.0 91.8(c) 154.0 54.3

1000 K 105.8 124.0 85.8 110.0(lq) 161.2 56.1

157.8(lq) 157.8 54.9 56.2 135.7 146.9 21.8(g)

21.5

186.7 56.9 82.6 101.7 144.8 261.8 52.3 72.8 78.9 76.4 99.4 97.9 96.1

193.6 57.4 83.5 103.8 149.3 269.2 54.3 76.0 80.3 78.6 102.1 101.1 99.9

26.8 66.6

27.5 72.2

27.9 83.3

46.5 72.4 129.(g)

49.1 76.2 131

51.1 79.5 132

182.0(c) 51.9 52.3 164.4

120.0(g) 58.5 54.6 175.2

120.6 65.0 55.7 182.8

26.8

28.5

30.1

28.0 138.9(c)

32.3(c) 37.7(lq) 37.7 222.6(lq) 108.8(g) 108.8

132.2

143.8

148.7

151.7

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SECTION 6

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

cap height base of text

Cp Substance TeH2 TeO2 Terbium Tb Thallium Tl, ⌬Ht ⫽ 0.38234 TlBr TlCl Tl2CO3 TlF TlI TlNO3 Tl2O Tl2O3 Tl2S Tl2SO4 Thorium Th, ⌬Ht ⫽ 2.731360 ThBr4 ThCl4, ⌬Ht ⫽ 5.0406 ThF4 ThI4 Th3N4 ThO2 ThOCl2 Th(SO4)2 Thullium Tm Tin Sn white, ⌬Ht ⫽ 2.0913 SnBr2 SnBr4 SnCl2 SnCl4 SnH4 SnI2 SnO SnO2, ⌬Ht ⫽ 1.88410 ⌬Ht ⫽ 1.26540 SnS, ⌬Ht ⫽ 0.67602 SnS2 Titanium Ti, ⌬Ht ⫽ 4.2893 TiB TiB2 TiBr2 TiBr3 TiBr4 TiC TiCl2

⌬Hm

⌬Hv

⌬Hs

400 K

600 K

800 K

1000 K

67.9

72.5

76.1

79.2

27.5(c) 53.5 53.6

30.1(lq) 59.5(c) 55.2(c)

30.1 75.5(lq) 59.4(lq)

30.1 67.8 59.4

53.9

66.8(lq) 60.6(c)

67.3 72.0(lq)

72.0

28.4

30.5

32.7

34.4

126.7

132.7

136.4

139.6

169.5 67.4 97.0 197.0

196.5 72.4 102.5 243.2

222.7 75.3 105.9 289.4

77.7 108.6

23.9 29.1 10.15 4.14 16.4 15.56 18.4 13.87 14.73 9.56 30.3 53 12 23.0 13.81 66.9 40.2 44.0 61.4

293

389

165 99.6 102.2

181

115.9 104.7

154

514 146.4 258 56.9

1218.0

16.84 7.03 7.2 11.9 12.8 9.20

14.15

247

232.2

296.1 102 43.5 86.8 34.9 19.1 105

425

28.9 158.0(lq) 83.3(c)

469

100.4 206.2 138.8 12.9 71

44.4 232

212

28.9(c)

28.7(lq)

106.8(g) 107.3 92.1(lq) 92.1

28.7 107.5 92.1

45.8 64.4

48.7 73.9

51.7 78.5

54.6 81.8

50.5 71.9

55.5 75.4

61.3 79.0

82.5

29.5 50.9 72.1 84.4 147.3 106.9 49.9 82.2

32.1 51.9 76.9 86.7 156.7 107.3 51.2 85.9

26.9 40.3 54.9 79.9 105.8 151.9(lq) 40.7 73.4

28.6 48.6 66.2 82.1 125.5 106.1(g) 47.7 78.4

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THERMODYNAMIC PROPERTIES

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

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Cp Substance TiCl3 TiCl4 TiF3 TiF4 TiH2 TiI2 TiI3 TiI4, ⌬Ht ⫽ 9.9106 TiN TiO, ⌬Ht ⫽ 4.2992 TiO2 rutile Ti2O3, ⌬Ht ⫽ 1.138197 Tungsten W WBr5 WBr6 WCl4 WCl5 WCl6, ⌬Ht ⫽ 4.1177 W(CO)6 WF6, ⌬Ht ⫽ 2.067⫺8.5 WO2 WO3, ⌬Ht ⫽ 1.49777 WOCl4 WOF4 WO2Cl2 Uranium U, ⌬Ht ⫽ 2.93672 ⌬Ht ⫽ 4.791772 UBr3 UBr4 UC UCl3 UCl4 UCl5 UCl6 UF3 UF4 UF5 UF6 UH3 UI4 UN UO2 UO3 U3O8 UOCl2 UO2Cl2 UO2F2

⌬Hm 9.97

⌬Hv 124 36.2

⌬Hs 166.3 222 97.9 217

19.8 66.9 41.8 58.0 105

58.4

673

52.31 17.1

806.7 81.5

20.5 6.60

68.1 52.7

4.10

27.05

73.4 45 5.0

9.14

76.6 67.8 56

417.1

43.9 55.2

119.2

46.4 44.8 35.6 20.9

193.0 141.4 75.3 50.2

42.7 33.5 19.19

221.8

70.7

130.6

28.90

851

100 79.2 72.0 26.65 666.3 550.2

525

48.20

400 K

600 K

800 K

1000 K

98.6 146.2(lq) 93 126.7(c) 39.3 87.0 117.5 148.1(c) 43.8 45.0 63.6 117.5

102.0 104.4(g) 98 100.2(g) 53.8 88.4 119.0 156.6(lq) 48.7 50.8 70.9 136.4

104.4 106.0 103 103.3 63.1 89.9 120.4(c) 25.7(g) 50.6 55.2 73.9 143.0

106.7 106.7 109 104.9 68.5 91.3 20.6(g) 27.8 52.1 59.1 75.3 146.4

24.9 166.(c) 192.5(c) 135.3 167.4(c) 192.5(c)

25.9 182.(lq) 156.3(g) 146.2(c) 129.5(g) 200.8(lq)

26.7 132.2(g) 157.0 106.7(g) 131.0 155.8(g)

27.6 132.5 157.4 107.2 131.8 156.6

132.4(g) 63.4 82.2 157.(c) 107.8 115.1

145.0 71.3 93.1 123.2(g) 119.8 135.6(c)

150.3 75.5 98.2 127.0 125.0

153.0 78.2 101.7 129.1 127.8

41.6

41.8

29.0

131.4 64.6 102.8 126.1 150.9 182.8 99.0 119.1 136.4 140.5(g) 50.9 140.6 52.2 72.7 88.9 266.0 101.9 118.1 113.9

34.8

140.1(c) 58.3 107.7 134.4 159.8(c) 214.0 104.9 125.0 143.1(c) 148.7 57.4 149.5(c) 56.3 79.8 95.3 290.7 109.6 126.2 122.5

163.2(lq) 60.3 113.6 142.0 186.7(lq) 158.8 111.0 130.9 166.6(lq) 152.2 66.1 165.7(lq) 58.3 83.2 99.0 304.2 115.1 130.0 126.7

163.2 62.2 119.9 162.5 134.5(g) 168.0 117.2 136.8 154.4 165.7 59.8 85.5

129.5

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SECTION 6

TABLE 6.4 Heats of Fusion, Vaporization, and Sublimation and Specific Heat at Various Temperatures of the Elements and Inorganic Compounds (Continued)

cap height base of text

Cp Substance Vanadium V VCl4 VF5 VN, ⌬Hdec ⫽ 227.62346 VO VO2, ⌬Ht ⫽ 4.2172 V2O3, ⌬Ht ⫽ 1.623⫺104.3 V2O4, ⌬Ht ⫽ 9.067 V2O5 VOCl3 Xenon Xe Ytterbium Yb Yttrium Y, ⌬Ht ⫽ 4.971485 Y2O3, ⌬Ht ⫽ 1.301057 Zinc Zn ZnBr2 ZnCl2 ZnF2 ZnO, ⌬Ht ⫽ 13.41020 Zn2SiO4 ZnSO4, ⌬Ht ⫽ 20.3740 Zirconium Zr, ⌬Ht ⫽ 4.02862 ZrB2 ZrBr2 ZrBr4 ZrC ZrCl2 ZrCl3 ZrCl4 ZrF2 ZrF4 ZrI2 ZrI3 ZrI4 ZrN ZrO2, ⌬Ht ⫽ 5.021205 ZrSiO4

6.2

⌬Hm 21.5 2.30 50.0 63 56.9 117.2 112.1 64.5

1.81

⌬Hv 459 41.4 44.5

400 K

600 K

516 42.5

26.2 161.7(lq)

27.5 100.1(g)

28.7 102.6

30.1 104.7

741

43.3 49.6 67.2 117.5 135.3 151.0

48.2 53.5 74.3 127.3 148.4 168.3

51.2 57.1 77.8 132.6 155.5 177.3

53.7 60.5 80.2 138.0 160.7 183.7

263.6 36.8 12.64

7.66

159

11.42 105

365

7.32 16.7 10.25

⌬Hs

20.79(g)

425

123.6 118 126 190.1

52.3

21.00 104.6 63 79.5 27 50 33 64.2 25.1

573

610.0

131.5

230

45.0

289

190 110.5 404 237.7

113 176 126.4

67.4 87.0

624

20.79

800 K

20.79

1000 K

20.79

27.3 113.3

28.5 121.3

29.9 124.7

31.5 126.9

26.3 70.1(c) 69.9(c) 66.9 49.4 129.4 116.0

28.6(c) 78.8(lq) 100.8(lq) 69.1 52.4 141.4 137.4

31.4(lq) 31.4 113.8 61.5(g) 100.8 100.8 71.4 73.7 54.1 55.5 153.4 165.4 139.7 142.0

25.9 57.5 87.9 129.3 43.6 76.0 101 125.4 70 113.5 95.0 105.9 131.0 44.8 63.9 114.6

27.3 65.8 90.2 133.3(c) 49.4 80.0 106 131.1(c) 76 124.0 96.6 106.7 134.6(c) 48.7 70.2 133.7

29.0 69.7 92.5 107.2(g) 52.3 83.1 109 106.5(g) 81 129.4 106.1 107.1(c) 107.6(g) 50.9 73.5 142.7

31.1 72.1 94.8 107.6 53.4 85.9 112 107.1 84 134.1 123.6 82.9(g) 107.6 52.7 75.7 147.3

CRITICAL PHENOMENA

The critical temperature, Tc , of a gas is the temperature above which the gas cannot be liquefied no matter how high the pressure.

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The critical pressure, Pc , is the lowest pressure which will liquefy the gas at its critical temperature. The critical volume, Vc , is the volume of 1 mol at the critical temperature and the critical pressure. It can be computed from the critical density, ␳c , as follows:

top of rh base of rh cap height base of text

Molecular weight (in g · mol⫺1 ) ⫽ Vc (in cm3 · mol⫺1) ␳c (in g · cm⫺3) The critical pressure, critical molar volume, and critical temperature are the values of the pressure, molar volume, and thermodynamic temperature at which the densities of coexisting liquid and gaseous phases just become identical. At this critical point, the critical compressibility factor, Zc , is: Zc ⫽

PcVc RTc

TABLE 6.5 Critical Properties Substance Acetaldehyde Acetic acid Acetic anhydride Acetone Acetonitrile Acetophenone Acetyl chloride Acetylene Acrylic acid Acrylonitrile Air Allene Allyl alcohol Aluminum tribromide Aluminum trichloride 2-Aminoethanol Ammonia Aniline Anthracene Antimony tribromide Antimony trichloride Argon Arsenic Arsenic trichloride Arsine Arsine-d3 Benzaldehyde Benzene Benzoic acid Benzonitrile Benzyl alcohol Biphenyl Bismuth tribromide Bismuth trichloride Boron pentafluoride Boron tribromide Boron trichloride

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

193 319.56 333 235.0 272.4 436.4 235 35.2 342 263 ⫺140.6 120 272.0 490 356 341 132.4 426 610 631.4 521 ⫺122.3 1400 318 99.9 98.9 422 288.90 479 426.3 422 516 946 906 205 308 178.8

55 57.1 39.5 46.4 47.7 38 58 60.6 56 45 37.2 54.0 56.4 28.5 26 44 111.3 49.5 28.6 56

5.57 5.786 4.0 4.700 4.85 3.85 5.88 6.14 5.67 4.56 3.77 5.47 5.71 2.89 2.63 4.46 11.28 4.89 2.90 5.67

154 171.3 290 209 173 386 204 113 210 210 92.7 162 203 310 261 196 72.5 287 554

0.286 0.351 0.352 0.278 0.237 0.311 0.325 0.231 0.343 0.253 0.313 0.247 0.286 0.860 0.510 0.312 0.235 0.324 0.322

48.1

4.87

270 74.6

0.84 0.536

58.4 63.3

5.91 6.41

252 133

0.720 0.588

45.9 48.31 41.55 41.55 42.4 38.0

4.65 4.895 4.21 4.21 4.3 3.85 11.96

324 255 341 339 334 502 301 261

0.327 0.306 0.358 0.304 0.324 0.307 1.49 1.21

4.87 3.87

272 266

0.921 0.441

118 48.1 38.2

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TABLE 6.5 Critical Properties (Continued) Substance Boron trifluoride Bromine Bromobenzene Bromochlorodifluoromethane Bromoethane Bromomethane Bromopentafluorobenzene 1-Bromopropane 2-Bromopropane Bromotrifluoromethane 1,2-Butadiene 1,3-Butadiene Butanal Butane Butanenitrile Butanoic acid 1-Butanol 2-Butanol 2-Butanone 1-Butene cis-2-Butene trans-2-Butene 3-Butenenitrile 1-Buten-3-yne Butyl acetate 1-Butylamine sec-Butylamine tert-Butylamine Butylbenzene sec-Butylbenzene tert-Butylbenzene Butyl benzoate Butyl butanoate Butylcyclohexane sec-Butylcyclohexane tert-Butylcyclohexane Butylcyclopentane Butyl ethyl ether 2-Butylhexadecafluorotetrahydrofuran Butylisopropylamine tert-Butyl methyl sulfide 1-Butyne 2-Butyne 4-Butyrolactone Carbon dioxide Carbon disulfide Carbon monoxide Carbon tetrachloride Carbon tetrafluoride Carbonyl chloride Carbonyl sulfide Cesium

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

⫺12.3 315 397 158.8 230.8 173.4 397 ⫺1.8 ⫺14.2 67.1 170.6 152 264.1 151.97 312.3 351 289.9 263.1 263.63 146.5 147.5 147.5 312.3 182 306.7 258.8 241.2 210.8 387.4 391 387 450 338 394 396 385.9 357.9 257.9 227.1

49.2 102 44.6 41.98 61.5 85 44.6

4.98 10.3 4.52 4.254 6.23 8.61 4.52

124 135 324 246 215 156

0.549 1.184 0.485 0.672 0.507 0.609

290.5 296.7 190.6 215.5 436 31.1 279 ⫺140.2 283.3 ⫺45.7 182 102 1806

39.2 44.4 42.7 42.6 37.34 38.3 39.8 43.56 41.47 41.52 39.7 40.5 40.5 38.3 49 31 41.9 41.4 37.9 28.5 29.1 29.3 26

3.97 4.50 4.33 4.32 3.784 3.88 4.03 4.414 4.202 4.207 4.02 4.10 4.10 3.88 4.96 3.14 4.25 4.20 3.84 2.89 2.94 2.97 2.63

200 219 221 258 255 285 290 275 269 267 240 238 238 265 202 400 277 278 292 497 510 490 561

31.1 26.4 26.3

3.15 2.67 2.66

534

0.462 0.462 0.76 0.247 0.245 0.279 0.228 0.242 0.304 0.270 0.276 0.270 0.234 0.240 0.236 0.253 0.258 0.290 0.264 0.263 0.250 0.270 0.263 0.273 0.318 0.292 0.63

30 15.86

3.04 1.607

390 588

0.262 0.707

46.5 50.2

4.71 5.09

220 221

0.246 0.246

72.8 78.0 34.5 45.0 36.9 56 58

7.38 7.90 3.50 4.56 3.74 5.67 5.88

94.0 173 93.1 276 140 190 140 300

0.468 0.41 0.301 0.558 0.629 0.52 0.44 0.44

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TABLE 6.5 Critical Properties (Continued) Substance Chlorine Chlorine pentafluoride Chlorine trifluoride Chlorobenzene 1-Chlorobutane 2-Chlorobutane 1-Chloro-1,1-difluoroethane 2-Chloro-1,1-difluoroethylene Chlorodifluoromethane 1-Chloro-2,3-epoxypropane Chloroethane Chloroform 1-Chlorohexane Chloromethane 2-Chloro-2-methylpropane Chloropentafluoroacetone Chloropentafluorobenzene Chloropentafluoroethane 1-Chloropentane 1-Chloropropane 2-Chloropropane 3-Chloropropene Chlorotrifluoromethane Chlorotrifluorosilane Chlorotrimethylsilane 1,2-Cresol 1,3-Cresol 1,4-Cresol Cyanogen Cyclobutane Cycloheptane Cyclohexane trans-Cyclohexanedimethanol Cyclohexanethiol Cyclohexanol Cyclohexanone Cyclohexene Cyclohexylamine Cyclopentane Cyclopentanethiol Cyclopentanone Cyclopentene 1-Cyclopentylheptane 1-Cyclopentylpentadecane Cyclopropane p-Cymene Decafluorobutane cis-Decahydronaphthalene trans-Decahydronaphthalene Decane Decanenitrile 1-Decanol 1-Decene

top of rh base of rh

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

143.8 142.6 153.5 359.3 268.9 247.5 137.1 127.5 96.1 351 187.3 263.3 321.5 143.1 234 137.6 297.9 80.1 295.4 230 212 241 29 35.4 224.7 424.5 432.7 431.5 126.7 186.8 316 280.4 451 390.9 376.9 379.9 287.33 341.5 238.6 360.4 353 232.9 406 506.9 124.7 379 113.3 429.2 414.0 344.6 348.8 413.9 343.3

76.1 51.9

7.71 5.26

124 230.9

0.573 0.565

44.6 36.4 39 40.7 44.0 49.1

4.52 3.69 3.95 4.12 4.46 4.98

308 312 305 231 197 165

0.365 0.297 0.303 0.435 0.499 0.525

52.0 54.0

5.27 5.47

199 239

0.324 0.504

65.9 39 28.4 31.8 31.9

6.679 3.95 2.88 3.22 3.229

139 295

0.353 0.314

252

0.613

45.2 46.6 47 38.98 34.2 31.6 49.4 45.0 50.8 62.2 49.2 36.7 40.2 34.85

4.58 4.72 4.76 3.946 3.47 3.20 5.01 4.56 5.15 6.30 4.99 3.72 4.07 3.531

254 230 234 180

0.309 0.341 0.336 0.579

282 309 277 145 210 390 308

0.384 0.346 0.391 0.360 0.267 0.252 0.273

42.0 39.5 42.9

4.26 4.0 4.35

327 312 292

0.306 0.315 0.281

44.49

4.508

260

0.27

53

5.37

268

0.314

19.2 10.1 54.2 2.80 22.93 31.6 31 20.8 32.1 22 21.89

1.94 1.02 5.49 2.84 2.323 3.20 3.14 2.11 3.25 2.23 2.218

649 1096 170 492 378 480 480 624

0.260 0.256 0.248 0.273 0.629 0.288 0.288 0.228

600 585

0.264 0.240

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TABLE 6.5 Critical Properties (Continued) Substance Decylcyclohexane Decylcyclopentane Deuterium (equilibrium) Deuterium (normal) Deuterium bromide Deuterium chloride Deuterium hydride (DH) Deuterium iodide Deuterium oxide Diallyl sulfide Diborane 1,2-Dibromo-2-chlorotrifluoroethane Dibromodifluoromethane 1,2-Dibromoethane Dibromomethane 1,2-Dibromotetrafluoroethane Dibutylamine Dibutyl ether Dibutyl sulfide 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene Dichlorodifluoromethane 1,1-Dichloroethane Dichlorodifluorosilane 1,2-Dichloroethane 1,1-Dichloroethylene cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene Dichlorofluoromethane 1,2-Dichlorohexafluoropropane Dichloromethane 1,2-Dichloropropane Dichlorosilane 1,1-Dichlorotetrafluoroethane 1,2-Dichlorotetrafluoroethane Dideuterium oxide (D2O) Diethanolamine 1,1-Diethoxyethane (Acetal) Diethylamine 1,4-Diethylbenzene Diethyl disulfide Diethylene glycol Diethyl ether 3,3-Diethylhexane 3,4-Diethylhexane 3,3-Diethyl-2-methylpentane 3,3-Diethylpentane Diethyl sulfide Difluoroamine (HNF2) 1,2-Difluorobenzene cis-Difluorodiazine

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

477 450 ⫺234.8 ⫺234.7 88.8 50.3 ⫺237.3 148.6 370.9 380 166 287.6

13.4 15.0 16.28 16.43

1.36 1.52 1.650 1.665

60.4 60.3

0.0668 0.0669

14.64

1.483

62.8

0.0481

213.8

21.66

55.6

0.360

39.5

4.00

40.8 71.1 71 33.49 30.7 29.7 24.7 40.5 38 39 40.82 50.0 34.5 53 51.3

4.13 7.2 7.19 3.393 3.11 3.01 2.50 4.10 3.85 3.95 4.136 5.07 3.50 5.4 5.20

54.4 51.1

5.51 5.18

60.2 44 46.1 32.6 32.1 215.7 32.3

6.10 4.49 4.67 3.30 3.252 21.86 3.27

37.3 27.7

198.3 309.9 310 214.7 334.4 311.0 377 424.2 411 412 111.80 250 95.8 288 222 271.1 234.4 178.43 172.9 237 304 176 145.5 145.63 371.0 442.0 254 226.84 384.8 368.9 408 193.59 354.7 345.7 366.8 337 284 130 284.2 ⫺1

Vc , cm3 · mol⫺1

249 242

0.843 0.776

329 517 500 537 360 359 372 217 236

0.790 0.250 0.260 0.272 0.408 0.408 0.395 0.558 0.419

225 218 224 224 196

0.440 0.445 0.433 0.433 0.522

193 226

0.440 0.500

294 297 349

0.582 0.582 0.363 0.301

3.758 2.81

301 480

0.243 0.280

46 35.9 23.8 23.0 25.0 26.4 39.1 93

4.66 3.638 2.41 2.33 2.53 2.67 3.96 9.42

316 280 510 519 501

0.336 0.265 0.279 0.274 0.284

318

0.284

300

0.381

70

7.09

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TABLE 6.5 Critical Properties (Continued) Substance trans-Difluorodiazine 1,1-Difluoroethane 1,1-Difluoroethylene Dihexyl ether Dihydrogen disulfide Dihydrogen heptasulfide Dihydrogen hexasulfide Dihydrogen octasulfide Dihydrogen pentasulfide Dihydrogen tetrasulfide Dihydrogen trisulfide Diisopentyl sulfide Diisopropyl ether 1,2-Dimethoxyethane Dimethoxymethane N,N-Dimethylacetamide Dimethylamine N,N-Dimethylaniline 2,2-Dimethylbutane 2,3-Dimethylbutane 3,3-Dimethyl-2-butanone 2,3-Dimethyl-1-butene 3,3-Dimethyl-1-butene 2,3-Dimethyl-2-butene 1,1-Dimethylcyclohexane cis-1,2-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane cis-1,3-Dimethylcyclohexane trans-1,3-Dimethylcyclohexane cis-1,4-Dimethylcyclohexane trans-1,4-Dimethylcyclohexane 1,1-Dimethylcyclopentane cis-1,2-Dimethylcyclopentane trans-1,2-Dimethylcyclopentane cis-1,3-Dimethylcyclopentane Dimethyl disulfide Dimethyl ether N,N-Dimethylformamide 2,2-Dimethylheptane 2,2-Dimethylhexane 2,3-Dimethylhexane 2,4-Dimethylhexane 2,5-Dimethylhexane 3,3-Dimethylhexane 3,4-Dimethylhexane 1,1-Dimethylhydrazine 2,4-Dimethyl-3-isopentane 2,3-Dimethyloctane 2,4-Dimethyloctane 2,5-Dimethyloctane 2,6-Dimethyloctane 2,7-Dimethyloctane

Tc , ⬚C

Pc , atm

Pc , MPa

⫺13 113.6 29.8 384 299 742 707 767 657 582 465 391 227.17 263 242.1 364 164.07 414 215.7 499.9 289.8 228 217 250.9 318 333.0 323.0 317.9 325 325.0 317.0 274 291.7 277.2 318.9 59.5 126.9 376.5 303.7 276.8 290.4 280.5 277.0 289.0 295.8 250 341.3

55 44.4 44.0 18 58.3 33 36 32 38.4 43.1 50.6

5.57 4.50 4.46 1.82 5.91 3.34 3.65 3.24 3.89 4.37 5.13

27.9 38.2 44.2 38.7 52.7 35.8 30.49 30.90

2.832 3.87 4.48 3.92 5.340 3.63 3.090 3.131

32.0 32.1 33.2 29.3 29.0 29.3 29.3 29.3 29.0 29.0 34.0 34.0 34.0

340.1 326.3 330 330 329.8

top of rh base of rh

Vc , cm3 · mol⫺1

␳c , g · cm⫺3

181 154 720

0.365 0.417 0.259

386 271

0.265 0.333

187

0.241

359 358

0.240 0.241

3.24 3.25 3.36 2.97 2.94 2.97 2.97 2.97 2.94 2.94 3.44 3.44 3.44

343 340 351 416 460 460 450 460 460 459 360 368 362

0.245 0.248 0.240 0.378 0.244 0.244 0.249 0.244 0.244 0.249 0.273 0.267 0.271

53.0 51.5 23.19 25.0 25.94 25.22 24.54 26.19 26.57 53.6 23.1

5.37 5.22 2.350 2.529 2.628 2.556 2.487 2.654 2.692 5.43 2.34

190 262 519 478 468 472 482 443 466 230 521

0.242 0.279 0.247 0.239 0.244 0.242 0.237 0.258 0.245 0.261 0.273

21.6 21.1 21.2 21.1 20.7

2.19 2.14 2.15 2.15 2.10

567 566 569 576 590

0.251 0.251 0.250 0.247 0.241

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TABLE 6.5 Critical Properties (Continued) Substance 3,3-Dimethyloctane 3,4-Dimethyloctane 3,5-Dimethyloctane 3,6-Dimethyloctane 4,5-Dimethyloctane 4,5-Dimethyloctane Dimethyl oxalate 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane 2,3-Dimethylphenol 2,4-Dimethylphenol 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol 3,5-Dimethylphenol 2,2-Dimethylpropane 2,2-Dimethyl-1-propanol 2,3-Dimethylpyridine 2,4-Dimethylpyridine 2,5-Dimethylpyridine 2,6-Dimethylpyridine 3,4-Dimethylpyridine 3,5-Dimethylpyridine Dimethyl sulfide N,N-Dimethyl-1,2-toluidine 1,4-Dioxane Diphenyl ether Diphenylmethane Dipropylamine Dipropyl ether Docosafluorodecane Dodecafluorocyclohexane Dodecafluorocyclohexene Dodecafluoro-1-hexene Dodecafluoropentane Dodecane 1-Dodecanol 1-Dodecene Dodecylbenzene Dodecylcyclopentane Ethane 1,2-Ethanediamine 1,2-Ethanediol Ethanethiol Ethanol Ethoxybenzene Ethyl acetate Ethyl acetoacetate Ethyl acrylate Ethylamine Ethylbenzene

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

339 341 333.2 335.2 333.8 339.1 355 247.4 264.3 246.7 263.3 449.7 434.5 433.8 427.9 456.7 442.5 160.7 276 382.3 373.9 371 350.7 410.7 394.1 229.9 395 314 493.7 494 282.7 257.5 269 184.1 188.7 181.3 149 385 405.9 384.5 501 477 32.3 319.8 445 225.5 240.9 374.0 250.2 400 279 183 344.00

21.9 22.1 21.6 21.6 21.8 22.1 39.2 27.4 28.70 27.01 29.07 48 43 48 42 49 36 31.55 39

2.22 2.24 2.19 2.19 2.21 2.24 3.97 2.773 2.908 2.737 2.946 4.86 4.36 4.86 4.26 4.96 3.65 3.197 3.95

557 551 555 562 548 546

0.255 0.258 0.256 0.253 0.260 0.261

416 393 418 414 470 509 470 509 552 611 307 319

0.241 0.255 0.240 0.242 0.26 0.24 0.26 0.24 0.27 0.25 0.238

316

0.339

201

0.309

238

0.370

407

0.249

754 718

0.226 0.260

1000

0.246

148 206 186 207 167

0.203 0.292 0.334 0.300 0.276

286

0.308

320 182 374

0.313 0.248 0.284

54.6 30.8 51.5 31 29.4 35.8 29.91 14.3 24

5.53 3.12 5.21 3.14 2.98 3.63 3.028 1.45 2.43

20.1 18.0 19 18.3 15.6 12.8 48.2 62.1 76 54.2 60.57 33.8 38.31

2.03 1.82 1.92 1.85 1.58 1.30 4.90 6.29 7.7 5.49 6.137 3.42 3.882

37.0 55.5 35.61

3.75 5.62 3.609

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TABLE 6.5 Critical Properties (Continued) Substance Ethyl benzoate Ethylbutanoate 2-Ethyl-1-butanol Ethyl crotonate Ethylcyclohexane Ethylcyclopentane 3-Ethyl-2,2-dimethylhexane 4-Ethyl-2,2-dimethylhexane 3-Ethyl-2,3-dimethylhexane 4-Ethyl-2,3-dimethylhexane 3-Ethyl-2,4-dimethylhexane 4-Ethyl-2,4-dimethylhexane 3-Ethyl-2,5-dimethylhexane 3-Ethyl-3,4-dimethylhexane Ethylene Ethylene glycol dimethyl ether Ethylene glycol ethyl ether acetate Ethylene glycol monobutyl ether Ethylene oxide Ethyl formate 3-Ethylhexane 2-Ethyl-1-hexanol Ethyl isopentanoate Ethyl isopropyl ether 2-Ethyl-1-methylbenzene 3-Ethyl-1-methylbenzene 4-Ethyl-1-methylbenzene Ethyl 3-methylbutanoate 1-Ethyl-1-methylcyclopentane Ethyl methyl ether 3-Ethyl-2-methylheptane 4-Ethyl-2-methylheptane 5-Ethyl-2-methylheptane 3-Ethyl-3-methylheptane 4-Ethyl-3-methylheptane 5-Ethyl-3-methylheptane 3-Ethyl-4-methylheptane 4-Ethyl-4-methylheptane Ethyl methyl ketone 3-Ethyl-2-methylpentane 3-Ethyl-3-methylpentane Ethyl 2-methylpropanoate Ethyl methyl sulfide 2-Ethylnaphthalene Ethyl nonanoate 3-Ethyloctane 4-Ethyloctane Ethyl octanoate 3-Ethylpentane 1,2-Ethylphenol 1,3-Ethylphenol

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

424 293 145.7 326 336 296.4 338.6 321.5 353.7 344.2 343.0 347.8 330.4 351.4 9.3 263 334.2

32 30.2

3.24 3.06

451 421

0.111 0.28

29.9 33.5 22.8 21.9 23.9 23.1 23.1 24.4 22.1 23.9 49.7 38.2 31.25

3.03 3.39 2.31 2.22 2.42 2.34 2.34 2.47 2.24 2.42 5.036 3.87 3.166

450 375 526 539 516 524 522 524 537 511 129 271 443

0.249 0.262 0.271 0.264 0.276 0.271 0.273 0.271 0.265 0.278 0.218 0.333 0.298

424

0.279

360.8 196 235.4 292.4 367.5 315 217.2 378 364 367 314.9 319 164.8 337.8 328.7 333.6 347.0 341.2 333.5 342.4 342.4 262.4 294.0 303.5 280 260 502 401 340 337 386 267.6 429.9 443.3

top of rh base of rh

71.0 46.8 25.74 27.2

7.275 4.74 2.608 2.76

140 229 455 494

0.314 0.323 0.251 0.264

30.0 28.0 29.0

3.04 2.84 2.94

460 490 470

0.26 0.24 0.26

29.5 43.4 22.0 21.6 21.6 22.8 22.5 22.0 22.5 22.8 41.0 26.65 27.71 30 42 31.0

2.99 4.40 2.23 2.19 2.19 2.31 2.28 2.23 2.28 2.31 4.154 2.700 2.808 3.04 4.26 3.14

221 544 545 555 532 530 541 533 525 267 443 455 410

0.272 0.262 0.261 0.256 0.267 0.269 0.263 0.267 0.271 0.270 0.258 0.351 0.28

521

0.300

21.6 21.5

2.19 2.18

561 552

0.241 0.258

28.53

2.891

416

0.241

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SECTION 6

cap height base of text

TABLE 6.5 Critical Properties (Continued) Substance 1,4-Ethylphenol Ethyl propanoate Ethyl propyl ether m-Ethyltoluene o-Ethyltoluene p-Ethyltoluene 3-Ethyl-2,2,3-trimethylpentane 3-Ethyl-2,2,4-trimethylpentane 3-Ethyl-2,3,4-trimethylpentane Ethyl vinyl ether Fluorine Fluorobenzene Fluoroethane Fluoromethane 4-Fluorotoluene Formaldehyde Formic acid 2-Furaldehyde Furan Germanium tetrachloride Glycerol Hafnium tetrabromide Hafnium tetrachloride Hafnium tetraiodide Helium (equilibrium) Helium-3 Helium-4 Heptadecane 1-Heptadecanol Heptane 1-Heptanol 2-Heptanol 3-Heptanol 2-Heptanone 1-Heptene Heptylcyclopentane Hexadecafluoroheptane Hexadecane 1-Hexadecene Hexadecylcyclopentane 1,5-Hexadiene Hexafluoroacetone Hexafluorobenzene Hexafluoroethane Hexamethylbenzene Hexane Hexanenitrile Hexanoic acid 1-Hexanol 2-Hexanol

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

443.3 272.9 227.1 364.0 378.0 367 372.9

33.18 32.1 28.1 30.1 29.0 25.4

3.362 3.25 2.837 3.04 2.94 2.57

345 244 490 460 479 503

0.296 0.361 0.245 0.261 0.256 0.283

342.2

23.4

2.37

518

0.275

369.2

25.1

2.54

506

0.281

202 ⫺129.0 286.94 102.2 44.7 316.4 135 315 397 217.1 276.9 453 473 450 643 ⫺267.96 ⫺269.85 ⫺267.96 460 736 267.1 359.5 335.2 332.3 338.4 264.2 406 201.7 444 444 518 234 84.1 243.6 19.7 494 234.5 360.7 389 337.2 312.8

40.17 51.47 44.91 49.6 58.0

4.07 5.215 4.551 5.03 5.88

260 66.2 357 169 124

0.277 0.574 0.269 0.284 0.274

65

6.6

105

0.286

58.1 54.3 38 66

5.89 5.50 3.85 6.69

57.0

5.86

218 330 255 415 304 528

2.261 1.13 2.24 13.0 14.0 27.0 30.18 29.81

0.2289 0.1182 0.227 1.32 1.42 2.74 3.058 3.021

0.312 0.650 0.361 1.20 1.05 1.30 0.06930 0.0414 0.0698 0.140 0.267 0.232 0.267 0.269

33.91 28.83 19.2 16.0 14 13.2 9.6 34 29.0 32.30

3.436 2.921 1.945 1.62 1.42 1.34 0.97 3.44 2.94 3.273

29.85 32.57 31.6 33.72 32.67

3.025 3.30 3.20 3.417 3.310

72.5 57.3 1006 960 428 435 432 421 402

0.271 0.246

664 930 933

0.584 0.243 0.241

328 329 335 224 600 368

0.250 0.505 0.505 0.617 0.271 0.233

381

0.268

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.151

THERMODYNAMIC PROPERTIES

cap height base of text

TABLE 6.5 Critical Properties (Continued) Substance 3-Hexanol 2-Hexanone 3-Hexanone 1-Hexene cis-2-Hexene trans-2-Hexene cis-3-Hexene trans-3-Hexene Hexylcyclopentane Hydrazine Hydrogen (equilibrium) Hydrogen (normal) Hydrogen bromide Hydrogen chloride Hydrogen cyanide Hydrogen deuteride Hydrogen fluoride Hydrogen iodide Hydrogen selenide Hydrogen sulfide Icosafluorononane Icosane 1-Icosanol Indane Iodine Iodobenzene Iodoethane Iodomethane 1-Iodopropane Isobutyl acetate Isobutylamine Isobutylbenzene Isobutyl bromide Isobutyl butanoate Isobutylcyclohexane Isobutyl formate Isobutyl isobutanoate Isobutyl 3-methylbutanoate Isobutyl propanoate Isopentyl acetate Isopentyl butanoate Isopentyl propanoate Isopropyl acetate Isopropylamine Isopropylbenzene Isopropylcycloheptane Isopropylcyclohexane Isopropylcyclopentane 4-Isopropylheptane Isopropylmethylamine 2-Isopropyl-1-methylbenzene 3-Isopropyl-1-methylbenzene 4-Isopropyl-1-methylbenzene

top of rh base of rh

Tc , ⬚C

Pc , atm

Pc , MPa

309.3 313.9 309.7 231.0 245 243 244 246.8 387.0 380 ⫺240.17 ⫺239.91 89.8 51.40 183.5 ⫺237.25 188 150.7 137 100.4 251 494 497 411.8 546 448 281.0 255 323 288 246 377 294.1 338 386 278 329 348 319 326 346 338 258 198.7 357.9 334.5 367 328 334.5 217.6 397 393 380

33.2 32.8 32.76 31.64 32.4 32.3 32.4 32.1 21.1 14.5 12.77 12.8 84.4 82.0 53.2 14.64 64 82.0 88 88.2 15.4 10.3 12.0 39.0 115 44.6

3.36 3.32 3.320 3.206 3.28 3.27 3.28 3.25 2.14 1.47 1.294 1.297 8.55 8.31 5.39 1.483 6.5 8.31 8.9 8.94 1.56 1.04 1.22 3.95 11.7 4.52

Vc , cm3 · mol⫺1

␳c , g · cm⫺3

348 351 351 350 350

0.242 0.240 0.240 0.240 0.240

96.1 65.4 65.0 100.0 81.0 139 62.8 69 131

0.333 0.0308 0.0310 0.809 0.45 0.195 0.048 0.29 0.976

98.5

0.31

1190

0.237

381 155 351

0.310 0.164 0.581

65

6.59

190

0.75

31.2 40.2 30.1

3.16 4.07 3.05

414 284 480

0.281 0.258 0.280

30.8 38.3

3.12 3.88

350

0.29

44.8 31.67

4.54 3.209

221 429

0.267 0.281

28 29.6 22.0

2.84 3.00 2.23

537

0.265

28.6 29.0 27.9

2.90 2.94 2.83

short standard long

DEAN #37261

LEFT

(McGHP)

6.152

INTERACTIVE

top of rh base of rh

SECTION 6

cap height base of text

TABLE 6.5 Critical Properties (Continued) Substance 3-Isopropyl-2-methylhexane Isopropyl methyl sulfide Isoquinoline Isoxazole Ketene Krypton Mercury Mercury(II) bromide Mercury(II) chloride Mercury(II) iodide Methane Methanethiol Methanol Methoxybenzene Methyl acetamide Methyl acetate Methyl acrylate Methylamine N-Methylaniline Methyl benzoate 2-Methyl-1,3-butadiene 3-Methyl-1,3-butadiene 2-Methylbutane 2-Methyl-1-butanethiol 2-Methyl-2-butanethiol Methyl butanoate 3-Methylbutanoic acid 2-Methyl-1-butanol 3-Methyl-1-butanol 2-Methyl-2-butanol 3-Methyl-2-butanol 3-Methyl-2-butanone 2-Methyl-1-butene 3-Methyl-1-butene 2-Methyl-2-butene Methylcyclohexane Methylcyclopentane Methyl dodecanoate N-Methylethylamine Methyl formate 2-Methylfuran 2-Methylheptane 3-Methylheptane 4-Methylheptane 2-Methylhexane 3-Methylhexane Methylhydrazine Methyl 2-hydroxybenzoate Methyl isobutanoate Methyl isocyanate 1-Methylnaphthalene 2-Methylnaphthalene 2-Methyloctane

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

359.3 276.4 530 278.9 380 ⫺63.75 1477 789 700 799 ⫺82.60 196.8 239.4 372.5 417 233.40 263 157.6 428 438 211 223 187.3 318.8 297.0 281.3 356 302.3 304.1 270.6 283.0 280.3 196.9 191.6 207.9 299.1 259.58 439 223.5 214.1 254 286.6 290.6 288.7 257.3 262.2 294 436 267.7 218 499 488 313.9

22.6

2.29

529

0.269

50.3

5.10

374

0.345

64 54.3 1587

6.5 5.50 160.8

145 91.2

0.290 0.9085

45.44 71.4 79.78 41.9

4.604 7.23 8.084 4.25

99.0 145 118

0.162 0.332 0.272 0.321

46.9 42 75.14 51.3 36 38.0 40.6 33.4

4.75 4.26 7.614 5.20 3.65 3.85 4.11 3.38

228 265 140 373 396 276 267 306

0.325 0.325 0.222 0.287 0.344 0.247 0.255 0.236

34.3 33.6 38.9 38.8 36.6 38.2 38.0 34.0 34.7 34.0 34.26 37.35

3.475 3.40 3.94 3.93 3.71 3.87 3.85 3.445 3.52 3.445 3.471 3.784

340

0.300

322 329 319

0.274 0.268 0.276

36.6 59.20 46.6 24.52 25.13 25.09 26.98 27.77 79.3

3.71 5.998 4.72 2.484 2.546 2.542 2.734 2.814 8.035

310 294 300 318 368 319 758 243 172 247 488 464 476 421 404 271

0.278 0.239 0.234 0.221 0.267 0.264 0.283 0.243 0.349 0.333 0.234 0.246 0.240 0.238 0.248 0.170

33.9 55 35.5 34.6 22.80

3.43 5.57 3.60 3.51 2.310

339

0.301

445 462

0.320 0.308

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.153

THERMODYNAMIC PROPERTIES

cap height base of text

TABLE 6.5 Critical Properties (Continued) Substance 2-Methylpentane 3-Methylpentane 2-Methyl-2,4-pentanediol Methyl pentanoate 2-Methyl-2-pentanol 2-Methyl-3-pentanol 3-Methyl-3-pentanol 4-Methyl-1-pentanol 4-Methyl-2-pentanol 3-Methyl-2-pentanone 4-Methyl-2-pentanone 2-Methyl-2-pentene cis-3-Methyl-2-pentene trans-3-Methyl-2-pentene cis-4-Methyl-2-pentene trans-4-Methyl-2-pentene 2-Methylpropanal 2-Methyl-1-propanamine N-Methylpropanamide 2-Methylpropane 2-Methyl-1-propanethiol 2-Methyl-2-propanethiol Methyl propanoate 2-Methylpropanoic acid 2-Methyl-1-propanol 2-Methyl-2-propanol 2-Methylpropene 2-Methylpropyl acetate Methyl propyl ether Methyl propyl sulfide 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 1-Methyl-2-pyrrolidinone 1-Methylstyrene 2-Methyltetrahydrofuran 2-Methylthiophene 3-Methylthiophene Methyl vinyl ether Morpholine Naphthalene Neon Niobium pentabromide Niobium pentachloride Niobium pentafluoride Nitric oxide Nitrobenzene Nitroethane Nitrogen-14 Nitrogen-15 Nitrogen chloride difluoride Nitrogen dioxide (equilibrium) Nitrogen trideuteride (ND3)

top of rh base of rh

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

224.6 231.4 405 294 286.4 302.9 302.5 330.4 301.3 298.8 298 245 245 248 217 220 240 246 412 134.70 286.4 257.0 257.5 332 274.6 233.1 144.73 288 203.2 301.0 347.9 371.9 373 448.7 381 264 333.1 337.7 163 345 475.3 ⫺228.71 737 534 464 ⫺92.9 459 284 146.94 146.8 64.3 158.2 132.4

29.91 30.85 33.9

3.031 3.126 3.43

367 367

0.235 0.235

34.1 34.7

3.46 3.52

42.4

4.30

380

0.269

32.3 32.4 32.4 32.3 30 30 41 40.2

3.27 3.28 3.28 3.27 3.04 3.04 4.15 4.07

371 351 351 350 360 360 274 278

0.270 0.240 0.240 0.240 0.234 0.234 0.263 0.263

35.83

3.630

263

0.221

39.5 36.5 42.39 39.20 39.48 31.2

4.00 3.7 4.295 3.972 4.000 3.16

282 292 273 275 239 414

0.312 0.302 0.272 0.270 0.235 0.281

45.4 44.2 46.4

4.60 4.48 4.70

33.6 37.1 47.9 48.9 47 54 39.98 27.2

3.40 3.76 4.85 4.95 4.76 54.7 4.051 2.77

62 64.6

6.28 6.55

292 288 292 311 397 267 275 275 205 253 407 41.7 469 400 155 58

0.319 0.323 0.319 0.319 0.298 0.322 0.356 0.356 0.283 0.344 0.31 0.4835 1.05 0.68 1.21 0.52

37 33.5 33.5 50.8 100

3.75 3.39 3.39 5.15 10.1

89.5 90.4

0.313 0.332

170

0.557

short standard long

DEAN #37261

LEFT

(McGHP)

6.154

INTERACTIVE

top of rh base of rh

SECTION 6

cap height base of text

TABLE 6.5 Critical Properties (Continued) Substance Nitrogen trifluoride Nitromethane 1-Nitropropane 2-Nitropropane Nitrous oxide Nitrosyl chloride Nitryl fluoride Nonadecane Nonane Nonanoic acid 1-Nonanol 1-Nonene Nonylbenzene Nonylcyclopentane Octadecafluorooctane Octadecane 1-Octadecanol 1-Octadecene Octafluorocyclobutane Octafluoronaphthalene Octafluoropropane Octamethylcyclotetrasiloxane Octane Octanenitrile Octanoic acid 1-Octanol 2-Octanol 1-Octene cis-2-Octene Octylcyclopentane Osmium tetroxide Oxygen Oxygen difluoride Ozone Pentachloroethane Pentadecane 1-Pentadecene Pentadecylcyclopentane 1,2-Pentadiene cis-1,3-Pentadiene 1,4-Pentadiene Pentafluorobenzene 2,3,4,5,6-Pentafluorotoluene 2,2,3,3,4-Pentamethylpentane 2,2,3,4,4-Pentamethylpentane Pentanal Pentane Pentanenitrile Pentanethiol Pentanoic acid 1-Pentanol 2-Pentanol

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

⫺39.3 315 402.0 344.8 36.434 167 76.3 483 321.5 438 404 319 468 437.4 229 472.3 474 466 115.31 399.9 72.7 313 295.6 401.3 422 379.4 356.5 293.6 307 421 132 ⫺118.56 ⫺58.0 ⫺12.10 373.0 433.9 431 507 230 223 205 258.9 275.5 370.7

44.7 57.9

4.53 5.87

173

0.352

71.596 90

7.2545 9.12

97.4 139

0.4525 0.471

11.0 22.6 23.7

1.12 2.29 2.40

23.1 18.7 16.3 16.4 12.73 14 11.2 27.48

2.34 1.89 1.65 1.66 1.29 1.42 1.13 2.784

26.5 13.2 24.6 28.1 26.1 27.41 27.18 26.40 27.3 17.7 170 49.77 48.9 53.8

1130 555

0.238 0.231

546 580 790

0.264 0.218 0.259

1070

0.238

325

0.616

2.69 1.33 2.49 2.85 2.64 2.777 2.754 2.675 2.77 1.79 17.2 5.043 4.95 5.45

299 970 492

0.628 0.306 0.232

490 494 464

0.266 0.278 0.242

15 14.4 10.1 40.2 39.4 37.4 34.7

1.52 1.46 1.02 4.07 3.99 3.79 3.52

880

0.241

276 275 276

0.248 0.248 0.248

25.5

2.58

508

0.280

354.2

23.7

2.40

521

0.273

281 196.6 337.2 324.6 370 315.0 287.3

35 33.26 35.3

3.55 3.370 3.58

333 311

0.259 0.237

35.3 38.38 36.27

3.58 3.889 3.675

340 326

0.300 0.270

73.4 97.7 88.9

0.436 0.553 0.540

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.155

THERMODYNAMIC PROPERTIES

cap height base of text

TABLE 6.5 Critical Properties (Continued) Substance 3-Pentanol 2-Pentanone 3-Pentanone 1-Pentene cis-2-Pentene trans-2-Pentene Pentyl acetate Pentylbenzene Pentyl formate 1-Pentyne Perchloryl fluoride Phenanthrene Phenol 1-Phenylhexadecane 1-Phenylpentadecane 1-Phenyltetradecane Phosgene Phosphine Phosphine-d3 Phosphonium chloride Phosphorus Phosphorus bromide difluoride Phosphorus chloride difluoride Phosphorus dibromide fluoride Phosphorus dichloride fluoride Phosphorus pentachloride Phosphorus trichloride Phosphorus trifluoride Phosphoryl chloride difluoride Phosphoryl trichloride Phosphoryl trifluoride Phthalic anhydride Piperidine Propadiene Propanal Propane 1,2-Propanediol 1,3-Propanediol Propanenitrile 1-Propanethiol 2-Propanethiol Propanoic acid 1-Propanol 2-Propanol 2-Propenal Propene 2-Propen-1-ol Propyl acetate Propylamine Propylbenzene Propyl butanoate Propylcyclopentane Propylcyclohexane Propylene oxide

Tc , ⬚C 286.5 287.93 288.31 191.63 202 198 332 406.8 303 220.3 95.3 596 421.1 535 526.9 519 182 51.3 50.4 49.1 721 113 89.2 254 189.9 372 290 ⫺1.9 150.7 329 73.4 537 321.0 120 231.3 96.68 352 385 288.2 262.5 244.2 331 263.7 235.2 233 91.9 272.0 276.6 223.9 365.20 327 358.7 336.7 209.1

top of rh base of rh

␳c , g · cm⫺3

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

36.46 36.9 34.81 36.4 34.7

3.694 3.729 3.527 3.69 3.52

301 336 293

0.286 0.256 0.239

304

0.231

25.7

2.60

550

0.269

40 53.0

4.05 5.37

60.5 12.7 13.3 14.0 56 64.5

6.13 1.29 1.35 1.42 5.67 6.54

278 161 554 229 1200 1140 1110 190

0.245 0.637 0.322 0.41 0.252 0.253 0.247 0.52

72.7

7.37

44.6

4.52

49.3

5.00 260

0.528

42.7 43.4

4.33 4.40

41.8 47 48.8 54.0 52.0 41.92 60 59 42.0

4.24 4.76 4.94 5.47 5.27 4.248 6.08 5.98 4.26

368 288 162 204 200 237 241 230

0.402 0.296 0.247 0.285 0.217 0.321 0.316 0.240

44.7 51.01 47.02 51 45.6

4.53 5.169 4.764 5.17 4.62

33.2 46.6 31.58

3.36 4.72 3.200

222 218.5 220 197 181 208 345 233 440

0.32 0.275 0.273 0.285 0.233 0.279 0.296 0.254 0.273

29.6 27.7 48.6

3.00 2.81 4.92

425

0.264

186

0.312

short standard long

DEAN #37261

LEFT

(McGHP)

6.156

INTERACTIVE

top of rh base of rh

SECTION 6

cap height base of text

TABLE 6.5 Critical Properties (Continued) Substance Propyl formate Propyl 2-methylpropanoate Propyl 3-methylpropanoate Propyl propanoate Propyne Pyridine Pyrrole Pyrrolidine Quinoline Radon Rhenium(VII) oxide Rhenium(VI) oxide tetrachloride Rubidium Selenium Silane Silicon chloride trifluoride Silicon tetrabromide Silicon tetrachloride Silicon tetrafluoride Silicon trichloride fluoride Spiro[2.2]pentane Styrene Sulfur Sulfur dioxide Sulfur hexafluoride Sulfur tetrafluoride Sulfur trioxide Tantalum pentabromide Tantalum pentachloride 1,2-Terphenyl 1,3-Terphenyl 1,4-Terphenyl 1,1,2,2-Tetrachlorodifluoroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetrachloromethane Tetradecafluoro-1-heptene Tetradecafluorohexane Tetradecafluoromethylcyclohexane Tetradecane 1-Tetradecene Tetradecylcyclopentane Tetraethylsilane Tetrafluoroethylene Tetrafluorohydrazine Tetrafluoromethane Tetrahydrofuran 1,2,3,4-Tetrahydronaphthalene Tetrahydropyran Tetrahydrothiophene 1,2,4,5-Tetramethylbenzene 2,2,3,3-Tetramethylbutane 2,2,3,3-Tetramethylhexane

Tc , ⬚C 264.9 316 336 305 129.3 346.9 366.6 295.1 509 104 669 508 1832 1493 ⫺3.5 34.5 390 234 ⫺14.0 165.4 233.3 363.8 1041 157.7 45.6 91.7 217.9 701 494 617.9 651.7 652.9 278 388.00 347.1 283.5 205.1 174.5 213.7 420.9 416 499 330.6 33.4 33.3 ⫺45.5 267.0 447 299.1 358.9 402 294.7 350.0

␳c , g · cm⫺3

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

40.1

4.06

285

0.309

55.5 55.96 62.6 55.2 48.0 62

5.62 5.67 6.34 5.59 4.86 6.28

164 243 200 238 437 139 334 161 250

0.245 0.325 0.335 0.300 0.300 1.6 0.95 0.34

47.8 34.2

4.84 3.47

37 36.7 35.3

3.75 3.72 3.57

326

0.521

36.3 116 77.8 37.1

3.68 11.7 7.88 3.76

347

0.300

122 198

0.5240 0.734

81

8.2

38.5 34.6 32.8 34

3.90 3.51 3.32 3.44

130 461 400 755 768 762 371

0.633 1.26 0.89 0.305 0.300 0.302 0.549

44.3 44.57

4.49 4.516

290 276

0.572 0.557

18.8 23 16 15.4 11.1 25.68 38.9 37 36.9 51.22 36.0 47.1

1.90 2.33 1.62 1.56 1.12 2.602 3.91 3.75 3.74 5.19 3.65 4.77

830

0.239

175

0.58

140 224 408 263

0.629 0.322 0.324 0.328

29 28.3 24.8

2.94 2.87 2.51

480 461 573

0.280 0.248 0.248

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

6.157

THERMODYNAMIC PROPERTIES

cap height base of text

TABLE 6.5 Critical Properties (Continued) Substance 2,2,3,4-Tetramethylhexane 2,2,3,5-Tetramethylhexane 2,2,4,4-Tetramethylhexane 2,2,4,5-Tetramethylhexane 2,2,5,5-Tetramethylhexane 2,3,3,4-Tetramethylhexane 2,3,3,5-Tetramethylhexane 2,3,4,4-Tetramethylhexane 2,3,4,5-Tetramethylhexane 3,3,4,4-Tetramethylhexane 2,2,3,3-Tetramethylpentane 2,2,3,4-Tetramethylpentane 2,2,4,4-Tetramethylpentane 2,3,3,4-Tetramethylpentane Tetramethylsilane Thiacyclopentane 2-Thiapropane Thiophene Thiophenol Thymol Tin(IV) chloride Titanium tetrachloride Toluene 1,2-Toluidine 1,3-Toluidine 1,4-Toluidine Toluonitrile Tributoxyborane Tributylamine 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane Trichlorofluorosilane Trichloromethane Trichloromethylsilane 1,2,3-Trichloropropane 1,2,2-Trichlorotrifluoroethane Tridecane 1-Tridecene Tridecylcyclopentane Triethanolamine Triethylamine Trifluoroacetic acid Trifluoroamine oxide (NOF3) 1,1,1-Trifluoroethane Trifluoromethane (Trifluoromethyl)benzene Trimethylamine 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene 2,2,3-Trimethylbutane 2,2,3-Trimethyl-1-butene

top of rh base of rh

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

Vc , cm3 · mol⫺1

347.3 328.2 337.1 325.4 308.4 360.0 337.0 353.5 340.1 373.6 334.6 319.6 301.6 334.6 175.49 358.8 230.0 306.3 416.4 425 318.7 365 318.60 434 434 433 450 472 365.3 272 329 271.1 198.1 165.4 263.3 244 378 214.2 402 401 488 514.3 262.5 218.2 29.5 73.2 25.8 286.8 159.64 391.4 376.0 364.2 258.1 260

23.4 22.4 22.2 21.9 21.6 24.5 22.9 23.9 23.1 25.4 27.05 25.68 24.52 26.80 27.84

2.37 2.27 2.25 2.22 2.19 2.48 2.32 2.42 2.34 2.57 2.741 2.602 2.485 2.716 2.821

525 540 535 544 573 514 531 518 530 506

0.271 0.263 0.266 0.262 0.248 0.277 0.268 0.275 0.269 0.281

362

0.244

54.6 56.16

5.53 5.69

201 219

0.309 0.385

37.0 46 40.54 43.1 42.2 45.2

3.75 4.66 4.108 4.37 4.28 4.58

351 340 316 343 343

0.742 0.558 0.292 0.312 0.312

19.6 18 42.4 41 49.5 43.5 35.3 54.0 32.4 39 33.7 16.6 16.8 11.9 24.2 29.92 32.15

1.99 1.82 4.30 4.15 5.02 4.41 3.57 5.47 3.28 3.95 3.42 1.68 1.70 1.21 2.45 3.032 3.258

863

0.267

294 256 248

0.454 0.513 0.554

239 348 348 325 780

0.500 0.430 0.424 0.576 0.236

37.1 47.7

3.76 4.83

389 204 169 194 133

0.26 0.559 0.593 0.434 0.525

40.34 34.09 31.90 30.86 29.15 28.6

4.087 3.454 3.232 3.127 2.954 2.90

254 430 430 433 398 400

0.233 0.280 0.280 0.278 0.252 0.245

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TABLE 6.5 Critical Properties (Continued) Substance 1,1,2-Trimethylcyclopentane 1,1,3-Trimethylcyclopentane cis,trans,cis-1,2,4-Trimethylcyclopentane cis,cis,trans-1,2,4-Trimethylcyclopentane 2,2,3-Trimethylheptane 2,2,4-Trimethylheptane 2,2,5-Trimethylheptane 2,2,6-Trimethylheptane 2,3,3-Trimethylheptane 2,3,4-Trimethylheptane 2,3,5-Trimethylheptane 2,3,6-Trimethylheptane 2,4,4-Trimethylheptane 2,4,5-Trimethylheptane 2,4,6-Trimethylheptane 2,5,5-Trimethylheptane 3,3,4-Trimethylheptane 3,3,5-Trimethylheptane 3,4,4-Trimethylheptane 3,4,5-Trimethylheptane 2,2,3-Trimethylhexane 2,2,4-Trimethylhexane 2,2,5-Trimethylhexane 2,4,7-Trimethyloctane 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane 2,3,4-Trimethylpentane 2,2,4-Trimethyl-1,3-pentanediol 2,3,6-Trimethylpyridine 2,4,6-Trimethylpyridine 2,4,6-Trimethyl-1,3,5-trioxane Tungsten(VI) oxide tetrachloride 1H-Undecafluoropentane Undecane 1-Undecene Uranium hexafluoride Vinyl acetate Vinyl chloride Vinyl fluoride Vinyl formate Water Xenon 1,2-Xylene 1,3-Xylene 1,4-Xylene Zirconium tetrabromide Zirconium tetrachloride Zirconium tetraiodide

␳c , g · cm⫺3

Tc , ⬚C

Pc , atm

Pc , MPa

306.4 296.4 298

29.0 27.9 27.7

2.94 2.83 2.81

306

28.4

2.88

338.6 321.4 325.0 320.3 344.4 340.6 339.7 331.0 327.2 333.8 317.2 329.8 349.4 336.5 347.8 339.7 315 300.6 295 335.7 290.4 270.9 300.5 293.4 398 381.4 379.9 290 509

22.4 21.4 21.4 21.0 22.9 22.6 22.1 21.6 21.9 22.1 21.2 21.9 23.4 22.9 23.4 22.1 24.6 23.4 23.0

2.27 2.17 2.17 2.13 2.32 2.29 2.24 2.19 2.22 2.24 2.15 2.22 2.37 2.32 2.37 2.24 2.49 2.37 2.33

546 552 559 573 538 538 547 560 541 544 560 550 526 579 524 547

0.261 0.258 0.256 0.248 0.265 0.265 0.260 0.254 0.263 0.262 0.254 0.259 0.271 0.246 0.271 0.261

519

0.247

26.94 25.34 27.83 26.94 25.6

2.730 2.568 2.820 2.730 2.59

436 468 455 461 364.6

0.262 0.244 0.251 0.248 0.4010

338

1.01

657

0.238 0.240 1.41 0.325 0.370 0.320 0.343 0.325 1.105 0.288 0.282 0.280 0.99 0.730 1.13

170.8 365.7 364 232.7 228.4 156.6 54.7 202 374.2 16.583 357.2 343.9 343.1 532 505 687

19.4 19.7 45.5 22.4 55.3 51.7 57 217.6 57.64 36.83 34.95 34.65

1.97 2.00 4.61 2.27 5.60 5.24 5.78 22.04 5.84 3.732 3.541 3.511

56.9

5.77

Vc , cm3 · mol⫺1

250 265 169 114 210 56.0 118 370 375 379 415 319 528

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SECTION 7

SPECTROSCOPY 7.1

X-RAY METHODS Table 7.1 Wavelengths of X-Ray Emission Spectra in Angstroms Table 7.2 Wavelengths of Absorption Edges in Angstroms Table 7.3 Critical X-Ray Absorption Energies in keV Table 7.4 X-Ray Emission Energies in keV Table 7.5 ␤ Filters for Common Target Elements Table 7.6 Interplanar Spacings for K␣1 Radiation, d versus 2␪ Table 7.7 Analyzing Crystals for X-Ray Spectroscopy Table 7.8 Mass Absorption Coefficients for K␣1 Lines and W L␣1 Line 7.2 ULTRAVIOLET-VISIBLE SPECTROSCOPY Table 7.9 Electronic Absorption Bands for Representative Chromophores Table 7.10 Ultraviolet Cutoffs of Spectrograde Solvents Table 7.11 Absorption Wavelength of Dienes Table 7.12 Absorption Wavelength of Enones and Dienones Table 7.13 Solvent Correction for Ultraviolet-Visible Spectroscopy Table 7.14 Primary Bands of Substituted Benzene and Heteroaromatics Table 7.15 Wavelength Calculation of the Principal Band of Substituted Benzene Derivatives 7.3 FLUORESCENCE Table 7.16 Fluorescence Spectroscopy of Some Organic Compounds Table 7.17 Fluorescence Quantum Yield Values 7.4 FLAME ATOMIC EMISSION, FLAME ATOMIC ABSORPTION, ELECTROTHERMAL (FURNACE) ATOMIC ABSORPTION, ARGON INDUCTION COUPLED PLASMA, AND PLASMA ATOMIC FLUORESCENCE Table 7.18 Detection Limits in ng/mL Table 7.19 Sensitive Lines of the Elements 7.4.1 Some Common Spectroscopic Relationships 7.5 INFRARED SPECTROSCOPY Table 7.20 Absorption Frequencies of Single Bonds to Hydrogen Table 7.21 Absorption Frequencies of Triple Bonds Table 7.22 Absorption Frequencies of Cumulated Double Bonds Table 7.23 Absorption Frequencies of Carbonyl Bands 7.5.1 Intensities of Carbonyl Bands 7.5.2 Position of Carbonyl Absorption Table 7.24 Absorption Frequencies of Other Double Bonds Table 7.25 Absorption Frequencies of Aromatic Bands Table 7.26 Absorption Frequencies of Miscellaneous Bands Table 7.27 Absorption Frequencies in the Near Infrared Table 7.28 Infrared Transmitting Materials Table 7.29 Infrared Transmission Characteristics of Selected Solvents 7.6 RAMAN SPECTROSCOPY Table 7.30 Raman Frequencies of Single Bonds to Hydrogen and Carbon Table 7.31 Raman Frequencies of Triple Bonds Table 7.32 Raman Frequencies of Cumulated Double Bonds Table 7.33 Raman Frequencies of Carbonyl Bands Table 7.34 Raman Frequencies of Other Double Bonds Table 7.35 Raman Frequencies of Aromatic Compounds Table 7.36 Raman Frequencies of Sulfur Compounds Table 7.37 Raman Frequencies of Ethers 7.1

7.2 7.3 7.5 7.8 7.10 7.14 7.14 7.15 7.16 7.18 7.19 7.20 7.21 7.22 7.23 7.23 7.24 7.25 7.25 7.28

7.28 7.29 7.34 7.38 7.41 7.41 7.47 7.49 7.50 7.53 7.53 7.54 7.57 7.58 7.64 7.67 7.68 7.71 7.71 7.76 7.77 7.78 7.79 7.82 7.84 7.85

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Table 7.38 Table 7.39 Table 7.40 7.7 NUCLEAR Table 7.41 Table 7.42 Table 7.43

Raman Frequencies of Halogen Compounds Raman Frequencies of Miscellaneous Compounds Principal Argon-Ion Laser Plasma Lines MAGNETIC RESONANCE Nuclear Properties of the Elements Proton Chemical Shifts Estimation of Chemical Shift for Protons of 9 CH2 9 and Methine Groups Table 7.44 Estimation of Chemical Shift of Proton Attached to a Double Bond Table 7.45 Chemical Shifts in Monosubstituted Benzene Table 7.46 Proton Spin Coupling Constants Table 7.47 Proton Chemical Shifts of Reference Compounds Table 7.48 Solvent Positions of Residual Protons in Incompletely Deuterated Solvents Table 7.49 Carbon-13 Chemical Shifts Table 7.50 Estimation of Chemical Shifts of Alkane Carbons Table 7.51 Effect of Substituent Groups on Alkyl Chemical Shifts Table 7.52 Estimation of Chemical Shifts of Carbon Attached to a Double Bond Table 7.53 Carbon-13 Chemical Shifts in Substituted Benzenes Table 7.54 Carbon-13 Chemical Shifts in Substituted Pyridines Table 7.55 Carbon-13 Chemical Shifts of Carbonyl Group Table 7.56 One-Bond Carbon-Hydrogen Spin Coupling Constants Table 7.57 Two-Bond Carbon-Hydrogen Spin Coupling Constants Table 7.58 Carbon-Carbon Spin Coupling Constants Table 7.59 Carbon-Fluorine Spin Coupling Constants Table 7.60 Carbon-13 Chemical Shifts of Deuterated Solvents Table 7.61 Carbon-13 Coupling Constants with Various Nuclei Table 7.62 Boron-11 Chemical Shifts Table 7.63 Nitrogen-15 (or Nitrogen-14) Chemical Shifts Table 7.64 Nitrogen-15 Chemical Shifts in Monosubstituted Pyridine Table 7.65 Nitrogen-15 Chemical Shifts for Standards Table 7.66 Nitrogen-15 to Hydrogen-1 Spin Coupling Constants Table 7.67 Nitrogen-15 to Carbon-13 Spin Coupling Constants Table 7.68 Nitrogen-15 to Fluorine-19 Spin Coupling Constants Table 7.69 Fluorine-19 Chemical Shifts Table 7.70 Fluorine-19 Chemical Shifts for Standards Table 7.71 Fluorine-19 to Fluorine-19 Spin Coupling Constants Table 7.72 Silicon-29 Chemical Shifts Table 7.73 Phosphorus-31 Chemical Shifts Table 7.74 Phosphorus-31 Spin Coupling Constants 7.8 MASS SPECTROMETRY 7.8.1 Correlation of Mass Spectra with Molecular Structure Table 7.75 Isotopic Abundances and Masses of Selected Elements 7.8.2 Mass Spectra and Structure Table 7.76 Condensed Table of Mass Spectra

7.1

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7.86 7,87 7.88 7.89 7.89 7.92

cap height base of text

7.94 7.95 7.96 7.97 7.98 7.98 7.99 7.102 7.102 7.103 7.104 7.105 7.106 7.107 7.108 7.108 7.109 7.110 7.110 7,111 7.112 7.115 7.115 7.115 7.116 7.116 7.117 7.118 7.118 7.118 7.119 7.122 7.123 7.123 7.124 7.126 7.128

X-RAY METHODS

An X-ray tube operating at a voltage V (in keV) emits a continuous X-ray spectrum, the minimum wavelength of which is given by ␭min ⫽ 12.398/V with the wavelength expressed in angstroms. For expressing the wavelength in kX units, divide by the factor 1.00202. Tables 7.1 and 7.2 are based

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TABLE 7.1 Wavelengths of X-Ray Emission Spectra in Angstroms Atomic No.

Element

K␣2

K␣1

3 4 5

Li Be B

6 7 8 9 10

C N O F Ne

44 31.60 23.71 18.31 14.616

11 12 13 14 15

Na Mg Al Si P

11.909 9.889

16 17 18 19 20

top of rh base of rh

K␤1

L␣1

L␤1

240 113 67

14.464

8.3392 7.1277

8.3367 7.1253 6.1549

11.617 9.558 7.981 6.7681 5.8038

407.6 251.0 169.8 123

S Cl Ar K Ca

5.3747 4.7305 4.1946 3.7446 3.3616

5.3720 4.7276 4.1916 3.7412 3.3583

5.0317 4.4031 3.8848 3.4538 3.0896

42.7 36.32

35.95

21 22 23 24 25

Sc Ti V Cr Mn

3.0345 2.75207 2.5073 2.29351 2.1057

3.0311 2.7484 2.5035 2.28962 2.1018

2.7795 2.5138 2.2843 2.08480 1.9102

31.33 27.39 24.26 21.67 19.45

31.01 27.02 23.85 21.28 19.12

26 27 28 29 30

Fe Co Ni Cu Zn

1.93991 1.79278 1.66169 1.54433 1.4389

1.93597 1.78892 1.65784 1.54051 1.4351

1.75653 1.62075 1.50010 1.39217 1.2952

17.567 15.968 14.566 13.330 12.257

17.255 15.667 14.279 13.053 11.985

31 32 33 34 35

Ga Ge As Se Br

1.3439 1.2580 1.1798 1.1088 1.0438

1.3400 1.2540 1.1758 1.1047 1.0397

1.20784 1.1289 1.0573 0.9921 0.9327

11.290 10.435 9.671 8.990 8.375

11.023 10.174 9.414 8.736 8.125

36 37 38 39 40

Kr Rb Sr Y Zr

0.9841 0.9296 0.8794 0.8330 0.7901

0.9801 0.9255 0.8752 0.8279 0.7859

0.8785 0.8286 0.7829 0.7407 0.7017

7.822 7.3181 6.8625 6.4485 6.0702

7.574 7.076 6.6237 6.2117 5.8358

41 42 43 44 45

Nb Mo Tc Ru Rh

0.7504 0.713543 0.6793 0.6474 0.6176

0.7462 0.70926 0.6749 0.6430 0.6132

0.6657 0.632253 0.6014 0.5725 0.5456

5.7240 5.4063 5.1126 4.8455 4.5973

5.4921 5.1768 4.8782 4.6204 4.3739

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TABLE 7.1 Wavelengths of X-Ray Emission Spectra in Angstroms (Continued) Atomic No.

Element

K␣2

K␣1

K␤1

46 47 48 49 50

Pd Ag Cd In Sn

0.5898 0.563775 0.5394 0.5165 0.4950

0.5854 0.559363 0.5350 0.5121 0.4906

0.5205 0.49701 0.4751 0.4545 0.4352

4.3676 4.1541 3.9563 3.7719 3.5999

4.1460 3.9344 3.7381 3.5552 3.3848

51 52 53 54 55

Sb Te I Xe Cs

0.4748 0.4558 0.4378 0.4204 0.4048

0.4703 0.4513 0.4333 0.4160 0.4003

0.4171 0.4000 0.3839 0.3685 0.3543

3.4392 3.2891 3.1485 3.016 2.9016

3.2256 3.0767 2.9373 2.807 2.8920

56 57 58 59 60

Ba La Ce Pr Nd

0.3896 0.3753 0.3617 0.3487 0.3565

0.3851 0.3707 0.3571 0.3441 0.3318

0.3408 0.3280 0.3158 0.3042 0.2933

2.7752 2.6651 2.5612 2.4627 2.3701

2.5674 2.4583 2.3558 2.2584 2.1666

61 62 63 64 65

Pm Sm Eu Gd Tb

0.3249 0.3137 0.3133 0.2932 0.2834

0.3207 0.3190 0.2985 0.2884 0.2788

0.2821 0.2731 0.2636 0.2544 0.2460

2.282 2.1994 2.1206 2.0460 1.9755

2.0796 1.9976 1.9202 1.8462 1.7763

66 67 68 69 70

Dy Ho Er Tm Yb

0.2743 0.2655 0.2572 0.2491 0.2415

0.2696 0.2608 0.2525 0.2444 0.2368

0.2376 0.2302 0.2226 0.2153 0.2088

1.9088 1.8447 1.7843 1.7263 1.6719

1.7100 1.6468 1.5873 1.5299 1.4756

71 72 73 74 75

Lu Hf Ta W Re

0.2341 0.2270 0.2203 0.213813 0.2076

0.2293 0.2222 0.2155 0.208992 0.2028

0.2021 0.1955 0.1901 0.184363 0.1789

1.6194 1.5696 1.5219 1.4764 1.4329

1.4235 1.3740 1.3270 1.2818 1.2385

76 77 78 79 80

Os Ir Pt Au Hg

0.2016 0.1959 0.1904 0.1851 0.1799

0.1968 0.1910 0.1855 0.1802 0.1750

0.1736 0.1685 0.1637 0.1590 0.1544

1.3911 1.3513 1.3130 1.2764 1.2411

1.1972 1.1578 1.1198 1.0836 1.0486

81 82 83 84 85

Tl Pb Bi Po At

0.1750 0.1703 0.1657 0.1608 0.1570

0.1701 0.1654 0.1608 0.1559 0.1521

0.1501 0.1460 0.1419 0.1382 0.1343

1.2074 1.1750 1.1439 1.1138 1.0850

1.0152 0.9822 0.9520 0.9222 0.8936

86 87 88 89 90

Rn Fr Ra Ac Th

0.1529 0.1489 0.1450 0.1414 0.1378

0.1479 0.1440 0.1401 0.1364 0.1328

0.1307 0.1272 0.1237 0.1205 0.1174

1.0572 1.030 1.0047 0.9799 0.9560

0.8659 0.840 0.8137 0.7890 0.7652

L␣1

L␤1

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TABLE 7.1 Wavelengths of X-Ray Emission Spectra in Angstroms (Continued) Atomic No.

Element

91 92 93 94 95 96 97 98 99 100

K␤1

top of rh base of rh

K␣2

K␣1

L␣1

L␤1

Pa U Np Pu Am

0.1344 0.1310 0.1278 0.1246 0.1215

0.1294 0.1259 0.1226 0.1195 0.1165

0.1143 0.1114 0.1085 0.1058 0.1031

0.9328 0.9105 0.8893 0.8682 0.8481

0.7422 0.7200 0.6984 0.6777 0.6576

Cm Bk Cf Es Fm

0.1186 0.1157 0.1130 0.1103 0.1077

0.1135 0.1107 0.1079 0.1052 0.1026

0.1005 0.0980 0.0956 0.0933 0.0910

0.8287 0.8098 0.7917 0.7740 0.7570

0.6388 0.6203 0.6023 0.5850 0.5682

TABLE 7.2 Wavelengths of Absorption Edges in Angstroms Atomic No.

Element

K

LI

L II

L III

3 4 5

Li Be B

226.5 110.68 66.289

6 7 8 9 10

C N O F Ne

43.68 30.99 23.32 17.913 14.183

11 12 13 14 15

Na Mg Al Si P

11.478 9.512 7.951 6.745 5.787

16 17 18 19 20

S Cl Ar K Ca

5.018 4.397 3.871 3.436 3.070

64.23 52.08 43.19 36.35 31.07

61.37 50.39 42.02 35.20

62.93 50.60 42.17 35.49

21 22 23 24 25

Sc Ti V Cr Mn

2.757 2.497 2.269 2.07012 1.896

26.83 23.39 20.52 16.7 16.27

30.16 26.83 23.70 17.9 18.90

30.53 27.37 24.26 20.7 19.40

26 27 28 29 30

Fe Co Ni Cu Zn

1.74334 1.60811 1.48802 1.38043 1.283

14.60 13.34 12.27 11.27 10.33

17.17 15.53 14.13 13.01 11.86

17.53 15.93 14.58 13.29 12.13

400 247.92 170 126.48 96.84

197.4 142.5 105.1 81.0

76.05

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TABLE 7.2 Wavelengths of Absorption Edges in Angstroms (Continued) Atomic No.

Element

K

LI

L II

L III

31 32 33 34 35

Ga Ge As Se Br

1.195 1.116 1.044 0.9800 0.9199

9.54 8.73 8.108 7.505 6.925

10.61 9.97 9.124 8.417 7.752

11.15 10.23 9.367 8.646 7.989

36 37 38 39 40

Kr Rb Sr Y Zr

0.8655 0.8155 0.7697 0.7276 0.6888

6.456 5.997 5.582 5.233 4.867

7.165 6.643 6.172 5.756 5.378

7.395 6.863 6.387 5.962 5.583

41 42 43 44 45

Nb Mo Tc Ru Rh

0.6529 0.61977 0.5888 0.5605 0.5338

4.581 4.299 4.064 3.841 3.626

5.025 4.719 4.427 4.179 3.942

5.223 4.912 4.629 4.369 4.130

46 47 48 49 50

Pd Ag Cd In Sn

0.5092 0.48582 0.4641 0.4439 0.4247

3.428 3.254 3.084 2.926 2.778

3.724 3.514 3.326 3.147 2.982

3.908 3.698 3.504 3.324 3.156

51 52 53 54 55

Sb Te I Xe Cs

0.4066 0.3897 0.3738 0.3585 0.3447

2.639 2.510 2.390 2.274 2.167

2.830 2.687 2.553 2.429 2.314

3.000 2.855 2.719 2.592 2.474

56 57 58 59 60

Ba La Ce Pr Nd

0.3314 0.3184 0.3065 0.2952 0.2845

2.068 1.973 1.891 1.811 1.735

2.204 2.103 2.009 1.924 1.843

2.363 2.258 2.164 2.077 1.995

61 62 63 64 65

Pm Sm Eu Gd Tb

0.2743 0.2646 0.2555 0.2468 0.2384

1.668 1.598 1.536 1.477 1.421

1.766 1.702 1.626 1.561 1.501

1.918 1.845 1.775 1.709 1.649

66 67 68 69 70

Dy Ho Er Tm Yb

0.2305 0.2229 0.2157 0.2089 0.2022

1.365 1.319 1.269 1.222 1.181

1.438 1.390 1.339 1.288 1.243

1.579 1.535 1.483 1.433 1.386

71 72 73

Lu Hf Ta

0.1958 0.1898 0.1839

1.140 1.099 1.061

1.198 1.154 1.113

1.341 1.297 1.255

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TABLE 7.2 Wavelengths of Absorption Edges in Angstroms (Continued) Atomic No.

Element

74 75

W Re

0.17837 0.1731

76 77 78 79 80

Os Ir Pt Au Hg

81 82 83 84 85

K

LI

top of rh base of rh

L II

L III

1.025 0.9901

1.074 1.036

1.215 1.177

0.1678 0.1629 0.1582 0.1534 0.1492

0.9557 0.9243 0.8914 0.8638 0.8353

1.001 0.9670 0.9348 0.9028 0.8779

1.140 1.106 1.072 1.040 1.009

Tl Pb Bi Po At

0.1447 0.1408 0.1371 0.1332 0.1295

0.8079 0.7815 0.7565 0.7322 0.7092

0.8436 0.8155 0.7891 0.7638 0.7387

0.9793 0.9503 0.9234 0.8970 0.8720

86 87 88 89 90

Rn Fr Ra Ac Th

0.1260 0.1225 0.1192 0.1161 0.1129

0.6868 0.6654 0.6446 0.6248 0.6061

0.7153 0.6929 0.6711 0.6500 0.6301

0.8479 0.8248 0.8027 0.7813 0.7606

91 92 93 94 95

Pa U Np Pu Am

0.1101 0.1068 0.1045 0.1018 0.0992

0.5875 0.5697 0.5531 0.5366 0.5208

0.6106 0.5919 0.5742 0.5571 0.5404

0.7411 0.7233 0.7042 0.6867 0.6700

96 97 98 99 100

Cm Bk Cf Es Fm

0.0967 0.0943 0.0920 0.0897 0.0875

0.5060 0.4913 0.4771 0.4636 0.4506

0.5246 0.5093 0.4945 0.4801 0.4665

0.6532 0.6375 0.6223 0.6076 0.5935

on the K and L wavelength values as published by Y. Cauchois and H. Hulubei (Tables de Constantes et Donne´es Nume´riques, I. Longueurs d’Onde des E´missions X et des Discontinuite´s d’Absorption X, Hermann, Paris, 1947) and by the International Union of Crystallography (International Tables for X-Ray Crystallography, Kynoch Press, Birmingham, England, 1962). Wavelength accuracy is only to about 1 in 25 000 except for the lines employed in X-ray diffraction work. Use of energy-proportional detectors for X-rays creates a need for energy values of K and L absorption edges (Table 7.3) and emission series (Table 7.4). These values were obtained by a conversion to keV of tabulated experimental wavelength values and smoothed by a fit to Moseley’s law. Although values are listed to 1 eV, chemical form may shift absorption edges and emission lines as much as 10 to 20 eV. S. Fine and C. F. Hendee [Nucelonics, 13(3):36 (1955)] also give values for K␤2 , L␥1 , and L␤2 lines. The relative intensities of X-ray emission lines from targets varies for different elements. However, one can assume a ratio of K␣1/K␣2 ⫽ 2 for the commonly used targets. The ratio of K␣2/K␤1 from these targets varies from 6 to 3.5. The intensities of K␤2 radiations amount to about 1 percent

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TABLE 7.3 Critical X-Ray Absorption Energies in keV Atomic No.

Element

K

LI

L II

L III

1 2 3 4 5

H He Li Be B

0.0136 0.0246 0.0547 0.112 0.187

6 7 8 9 10

C N O F Ne

0.284 0.400 0.532 0.692 0.874

0.048

0.022

11 12 13 14 15

Na Mg Al Si P

1.08 1.30 1.559 1.838 2.142

0.055 0.0628 0.0870 0.118 0.153

0.034 0.0502 0.0720 0.0977 0.128

16 17 18 19 20

S Cl Ar K Ca

2.469 2.822 3.200 3.606 4.038

0.193 0.238 0.287 0.341 0.399

0.163 0.202 0.246 0.295 0.350

0.162 0.201 0.244 0.292 0.346

21 22 23 24 25

Sc Ti V Cr Mn

4.496 4.966 5.467 5.988 6.542

0.462 0.530 0.604 0.679 0.762

0.411 0.462 0.523 0.584 0.656

0.407 0.456 0.515 0.574 0.644

26 27 28 29 30

Fe Co Ni Cu Zn

7.113 7.713 8.337 8.982 9.662

0.849 0.929 1.02 1.10 1.20

0.722 0.798 0.877 0.954 1.05

0.709 0.783 0.858 0.935 1.02

31 32 33 34 35

Ga Ge As Se Br

10.39 11.10 11.87 12.65 13.48

1.30 1.42 1.529 1.66 1.791

1.17 1.24 1.358 1.472 1.599

1.14 1.21 1.32 1.431 1.552

36 37 38 39 40

Kr Rb Sr Y Zr

14.32 15.197 16.101 17.053 17.998

1.92 2.064 2.212 2.387 2.533

1.729 1.863 2.004 2.171 2.308

1.674 1.803 1.937 2.096 2.224

41 42 43

Nb Mo Tc

18.986 20.003 21.050

2.700 2.869 3.045

2.467 2.630 2.796

2.372 2.525 2.680

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TABLE 7.3 Critical X-Ray Absorption Energies in keV (Continued) Atomic No.

Element

K

LI

L II

L III

44 45

Ru Rh

22.117 23.210

3.227 3.404

2.968 3.139

2.839 2.995

46 47 48 49 50

Pd Ag Cd In Sn

24.356 25.535 26.712 27.929 29.182

3.614 3.828 4.019 4.226 4.445

3.338 3.547 3.731 3.929 4.139

3.181 3.375 3.541 3.732 3.911

51 52 53 54 55

Sb Te I Xe Cs

30.497 31.817 33.164 34.551 35.974

4.708 4.953 5.187 5.448 5.706

4.391 4.621 4.855 5.103 5.360

4.137 4.347 4.559 4.783 5.014

56 57 58 59 60

Ba La Ce Pr Nd

37.432 38.923 40.43 41.99 43.57

5.995 6.264 6.556 6.837 7.134

5.629 5.902 6.169 6.446 6.728

5.250 5.490 5.728 5.968 6.215

61 62 63 64 65

Pm Sm Eu Gd Tb

45.19 46.85 48.51 50.23 52.00

7.431 7.742 8.059 8.383 8.713

7.022 7.316 7.624 7.942 8.258

6.462 6.720 6.984 7.251 7.520

66 67 68 69 70

Dy Ho Er Tm Yb

53.77 55.61 57.47 59.38 61.31

9.053 9.395 9.754 10.12 10.49

8.587 8.918 9.270 9.622 9.985

7.795 8.074 8.362 8.656 8.949

71 72 73 74 75

Lu Hf Ta W Re

63.32 65.37 67.46 69.51 71.67

10.87 11.28 11.68 12.09 12.52

10.35 10.75 11.14 11.54 11.96

9.248 9.567 9.883 10.20 10.53

76 77 78 79 80

Os Ir Pt Au Hg

73.87 76.11 78.35 80.67 83.08

12.97 13.41 13.865 14.351 14.838

12.38 12.82 13.26 13.731 14.205

10.86 11.21 11.55 11.92 12.278

81 82 83 84 85

Tl Pb Bi Po At

85.52 87.95 90.54 93.16 95.73

15.344 15.861 16.386 16.925 17.481

14.695 15.200 15.709 16.233 16.777

12.65 13.03 13.42 13.81 14.21

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TABLE 7.3 Critical X-Ray Absorption Energies in keV (Continued) Atomic No.

Element

86 87 88 89 90

Rn Fa Ra Ac Th

91 92 93 94 95 96 97 98 99 100

K

LI

L II

L III

98.45 101.1 103.9 107.7 109.8

18.054 18.628 19.228 19.829 20.452

17.331 17.893 18.473 19.071 19.673

14.61 15.02 15.44 15.86 16.278

Pa U Np Pu Am

112.4 115.0 118.2 121.2 124.3

21.096 21.757 22.411 23.117 23.795

20.295 20.944 21.585 22.250 22.935

16.720 17.163 17.606 18.062 18.524

Cm Bk Cf Es Fm

127.2 131.3 133.6 138.1 141.5

24.502 25.231 26.010 26.729 27.503

23.629 24.344 25.070 25.824 26.584

18.992 19.466 19.954 20.422 20.912

K␣1

L ␤1

L ␣1

TABLE 7.4 X-Ray Emission Energies in keV Atomic No.

Element

K␤1

3 4 5

Li Be B

0.052 0.110 0.185

6 7 8 9 10

C N O F Ne

0.282 0.392 0.523 0.677 0.851

11 12 13 14 15

Na Mg Al Si P

1.067 1.297 1.553 1.832 2.136

1.041 1.254 1.487 1.740 2.015

16 17 18 19 20

S Cl Ar K Ca

2.464 2.815 3.192 3.589 4.012

2.308 2.622 2.957 3.313 3.691

0.344

0.341

21 22 23

Sc Ti V

4.460 4.931 5.427

4.090 4.510 4.952

0.399 0.458 0.519

0.395 0.452 0.512

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TABLE 7.4 X-Ray Emission Energies in keV (Continued) Atomic No.

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Element

K␤1

K␣1

L ␤1

L ␣1

24 25

Cr Mn

5.946 6.490

5.414 5.898

0.581 0.647

0.571 0.636

26 27 28 29 30

Fe Co Ni Cu Zn

7.057 7.649 8.264 8.904 9.571

6.403 6.930 7.477 8.047 8.638

0.717 0.790 0.866 0.948 1.032

0.704 0.775 0.849 0.928 1.009

31 32 33 34 35

Ga Ge As Se Br

10.263 10.981 11.725 12.495 13.290

9.251 9.885 10.543 11.221 11.923

1.122 1.216 1.317 1.419 1.526

1.096 1.186 1.282 1.379 1.480

36 37 38 39 40

Kr Rb Sr Y Zr

14.112 14.960 15.834 16.736 17.666

12.649 13.394 14.164 14.957 15.774

1.638 1.752 1.872 1.996 2.124

1.587 1.694 1.806 1.922 2.042

41 42 43 44 45

Nb Mo Tc Ru Rh

18.621 19.607 20.612 21.655 22.721

16.614 17.478 18.370 19.278 20.214

2.257 2.395 2.538 2.683 2.834

2.166 2.293 2.424 2.558 2.696

46 47 48 49 50

Pd Ag Cd In Sn

23.816 24.942 26.093 27.274 28.483

21.175 22.162 23.172 24.207 25.270

2.990 3.151 3.316 3.487 3.662

2.838 2.984 3.133 3.287 3.444

51 52 53 54 55

Sb Te I Xe Cs

29.723 30.993 32.292 33.644 34.984

26.357 27.471 28.610 29.779 30.970

3.843 4.029 4.220 4.422 4.620

3.605 3.769 3.937 4.111 4.286

56 57 58 59 60

Ba La Ce Pr Nd

36.376 37.799 39.255 40.746 42.269

32.191 33.440 34.717 36.023 37.359

4.828 5.043 5.262 5.489 5.722

4.467 4.651 4.840 5.034 5.230

61 62 63 64 65

Pm Sm Eu Gd Tb

43.811 45.400 47.027 48.718 50.391

38.726 40.124 41.529 42.983 44.470

5.956 6.206 6.456 6.714 6.979

5.431 5.636 5.846 6.059 6.275

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TABLE 7.4 X-Ray Emission Energies in keV (Continued) Atomic No.

Element

K␤1

K␣1

L ␤1

L ␣1

66 67 68 69 70

Dy Ho Er Tm Yb

52.178 53.934 55.690 57.487 59.352

45.985 47.528 49.099 50.730 52.360

7.249 7.528 7.810 8.103 8.401

6.495 6.720 6.948 7.181 7.414

71 72 73 74 75

Lu Hf Ta W Re

61.282 63.209 65.210 67.233 69.298

54.063 55.757 57.524 59.310 61.131

8.708 9.021 9.341 9.670 10.008

7.654 7.898 8.145 8.396 8.651

76 77 78 79 80

Os Ir Pt Au Hg

71.404 73.549 75.736 77.968 80.258

62.991 64.886 66.820 68.794 70.821

10.354 10.706 11.069 11.439 11.823

8.910 9.173 9.441 9.711 9.987

81 82 83 84 85

Tl Pb Bi Po At

82.558 84.922 87.335 89.809 92.319

72.860 74.957 77.097 79.296 81.525

12.210 12.611 13.021 13.441 13.873

10.266 10.549 10.836 11.128 11.424

86 87 88 89 90

Rn Fr Ra Ac Th

94.877 97.483 100.136 102.846 105.592

83.800 86.119 88.485 90.894 93.334

14.316 14.770 15.233 15.712 16.200

11.724 12.029 12.338 12.650 12.966

91 92 93 94 95

Pa U Np Pu Am

108.408 111.289 114.181 117.146 120.163

95.851 98.428 101.005 103.653 106.351

16.700 17.218 17.740 18.278 18.829

13.291 13.613 13.945 14.279 14.618

96 97 98 99 100

Cm Bk Cf Es Fm

123.235 126.362 129.544 132.781 136.075

109.098 111.896 114.745 117.646 120.598

19.393 19.971 20.562 21.166 21.785

14.961 15.309 15.661 16.018 16.379

of that of the corresponding K␣1 radiation. In practical applications these ratios have to be corrected for differential absorption in the window of the tube and air path, the ratio of scattering factors for and differential absorption in the crystal, and for sensitivity characteristics of the detector. Generalizing, the intensities of radiations from the K and L series are as follows:

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Emission line

K␣1

K␣2

K␤1

K␤2

L␣1

L␣2

L␤1

L␤2

L␥1

Relative intensity

500

250

80– 150

5

100

10

30

60

40

For angles at which the K␣1 , K␣2 doublet is not resolved, a mean wavelength [K␣¯ ⫽ (2K␣1 ⫹ K␣2)/3] can be used. Filters. The K spectra of the light metals, often used as target material in the production of Xrays for diffraction studies, contain three strong lines, ␣1 , ␣2 and ␤1 , of which the ␣ lines form a doublet with a narrow wavelength separation. The K␤ radiation can be eliminated by using a thin foil filter, usually of the element of next lower atomic number to that of the target element: the K␣ lines are transmitted with a relatively small loss of intensity. Table 7.5, restricted to the K wavelengths of target elements in common use, lists the calculated thicknesses of ␤ filters required to reduce the K␤1/K␣1 integrated intensity ratio to 1⁄100. Interplanar Spacings. Diffractometer alignment procedures require the use of a well-prepared polycrystalline specimen. Two standard samples found to be suitable are silicon and ␣-quartz (including Novaculite). The 2␪ values of several of the most intense reflections for these materials are listed in Table 7.6 (Tables of Interplanar Spacings d vs. Diffraction Angle 2␪ for Selected Targets, Picker Nuclear, White Plains, N.Y., 1966). To convert to d for K␣¯ or to d for K␣2 , multiply the tabulated d value (Table 7.6) for K␣1 by the factor given below:

Element

K␣¯

K␣2

W Ag Mo Cu Ni Co Fe Cr

1.007 69 1.002 63 1.002 02 1.000 82 1.000 77 1.000 72 1.000 67 1.000 57

1.023 07 1.007 89 1.006 04 1.002 48 1.002 32 1.002 16 1.002 04 1.001 70

Analyzing Crystals. The range of wavelengths usable with various analyzing crystals are governed by the d spacings of the crystal planes and by the geometric limits to which the goniometer can be rotated. The d value should be small enough to make the angle 2␪ greater than approximately 10 or 15 deg, even at the shortest wavelength used: otherwise excessively long analyzing crystals would be needed to prevent the direct fluorescent beam from entering the detector. A small d value is also favorable for producing a large dispersion of the spectrum to give good separation of adjacent lines. On the other hand, a small d value imposes an upper limit to the range of wavelengths that can be analyzed. Actually the goniometer is limited mechanically to about 150 deg for a 2␪ value. A final requirement is the reflection efficiency and minimization of higher-order reflections. Table 7.7 gives a list of crystals commonly used for X-ray spectroscopy.

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TABLE 7.5 ␤ Filters for Common Target Elements K␤1 K␣1 ⫽ 1⁄100 Target Element

˚ K␣¯ , A

Excitation Voltage, keV

Ag Mo Cu Ni Co Fe

0.560834 0.71069 1.54178 1.65912 1.79021 1.93728

25.52 20.00 8.981 8.331 7.709 7.111

Cr

2.29092

5.989

Absorber

Thickness, mm

g/cm2

% Loss K␣1

Pd Zr Ni Co Fe Mn MnO2 V V2O5

0.062 0.081 0.015 0.013 0.012 0.011 0.026 0.011 0.036

0.074 0.053 0.013 0.011 0.009 0.008 0.013 0.007 0.012

60 57 45 42 39 38 45 37 48

L ␣1 W

% Loss L ␣1

L ␤1 L ␣1 ⫽ 1⁄100

1.4763

10.200

Cu

0.035

77

TABLE 7.6 Interplanar Spacings for K␣1 Radiation, d versus 2␪

␣-quartz (Including Novaculite) hkl ˚) d(A W K␣1: Ag K␣1: Mo K␣1: Cu K␣1: Ni K␣1: Co K␣1: Fe K␣1: Cr K␣1:

2␪ 2␪ 2␪ 2␪ 2␪ 2␪ 2␪ 2␪

100 4.260

101 3.343

110 2.458

102 2.282

200 2.128

112 1.817

202 1.672

211 1.541

203 1.375

301 1.372

2.81 7.53 9.55 20.83 22.44 24.24 26.27 31.18

3.58 9.60 12.18 26.64 28.71 31.04 33.66 40.05

4.87 13.07 16.59 36.52 39.42 42.68 46.38 55.52

5.25 14.08 17.88 39.45 42.60 46.15 50.20 60.22

5.63 15.10 19.19 42.44 45.85 49.71 54.11 65.09

6.59 17.71 22.51 50.16 54.28 58.98 64.38 78.11

7.17 19.26 24.49 54.86 59.44 64.68 70.75 86.42

7.78 20.91 26.61 59.98 65.08 70.96 77.83 95.96

8.72 23.47 29.89 68.14 74.15 81.16 89.50 112.73

8.74 23.52 29.96 68.31 74.34 81.38 89.74 113.11

Silicon hkl ˚) d(A W K␣1: Ag K␣1: Mo K␣1: Cu K␣1: Ni K␣1: Co K␣1: Fe K␣1: Cr K␣1:

111 220 311 400 331 422 511,333 440 531 620 3.1353 1.91997 1.63736 1.357630 1.24584 1.1085 1.0451 0.959986 0.917922 0.858637 2␪ 2␪ 2␪ 2␪ 2␪ 2␪ 2␪ 2␪

3.82 10.24 12.99 28.44 30.66 33.15 35.97 42.83

6.24 16.75 21.29 47.30 51.16 55.53 60.55 73.21

7.32 19.67 25.02 56.12 60.83 66.22 72.48 88.72

8.83 23.78 30.28 69.13 75.26 82.42 90.96 114.97

9.62 10.82 11.48 25.95 29.23 31.04 33.08 37.32 39.67 76.38 88.03 94.96 83.42 96.80 104.96 91.77 107.59 117.71 101.97 121.67 135.70 133.53

12.50 33.88 43.36 106.71 119.42 137.42

13.07 35.48 45.45 114.10 129.12 154.04

13.98 38.02 48.79 127.55 149.76

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TABLE 7.7 Analyzing Crystals for X-Ray Spectroscopy

Crystal Quartz Aluminum Topaz Quartz Lithium fluoride Silicon Quartz Lithium fluoride Sodium chloride Calcium fluoride Quartz Quartz Pentaerythritol (PET) Ethylenediamine tartrate (EDT) Ammonium dihydrogen phosphate (ADP) Gypsum Mica Potassium hydrogen phthalate (KAP) Lead palmitate Strontium behenate Lead stearate

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Reflecting Plane

2d Spacing, ˚ A

5052 111 303 2023 220 111 112 200 200 111 1011 1010 002 020 110 020 002 1011

1.624 2.338 2.712 2.750 2.848 3.135 3.636 4.028 5.639 6.32 6.686 8.50 8.742 8.808 10.648 15.185 19.92 26.4 45.6 61.3 100.4

Reflectivity Low High Medium Low High High Medium High High High High Medium High Medium Low Medium Low Medium

Medium

The long-wavelength analyzers are prepared by dipping an optical flat into the film of the metal fatty acid about 50 times to produce a layer 180 molecules in thickness. ˚ . Pentaerythritol (PET) Lithium fluoride is the optimum crystal for all wavelengths less than 3 A and potassium hydrogen phthalate (KAP) are usually the crystals of choice for wavelengths from 3 ˚ . Two crystals suppress even-ordered reflections: silicon (111) and calcium fluoride (111). to 20 A Mass Absorption Coefficients. Radiation traversing a layer of substance is diminished in intensity by a constant fraction per centimeter thickness x of material. The emergent radiant power P, in terms of incident radiant power P0 , is given by P ⫽ P0 exp (⫺ ␮x) which defines the total linear absorption coefficient ␮. Since the reduction of intensity is determined by the quantity of matter traversed by the primary beam, the absorber thickness is best expressed on a mass basis, in g/cm2. The mass absorption coefficient ␮/␳, expressed in units cm2/g, where ␳ is the density of the material, is approximately independent of the physical state of the material and, to a good approximation, is additive with respect to the elements composing a substance. Table 7.8 contains values of ␮/␳ for the common target elements employed in X-ray work. A more extensive set of mass absorption coefficients for K, L, and M emission lines within the wave˚ is contained in Heinrich’s paper in T. D. McKinley, K. F. J. Heinrich, length range from 0.7 to 12 A and D. B. Wittry (eds.), The Electron Microprobe, Wiley, New York, 1966, pp. 351–377. This article should be consulted to ascertain the probable accuracy of the values and for a compilation of coefficients and exponents employed in the computations.

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TABLE 7.8 Mass Absorption Coefficients for K␣1 Lines and W L␣1 Line Emitter ˚ wavelength, A

Ag K␣1 0.559

Mo K␣1 0.709

Cu K␣1 1.541

0.43 0.37 0.50 1.2 2.5

Ni K␣1 1.658

Co K␣1 1.789

Fe K␣1 1.936

Cr K␣1 2.290

W L␣1 1.476

Absorber 1 2 3 4 5

H He Li Be B

0.37 0.16 0.18 0.22 0.30

0.38 0.18 0.22 0.30 0.45

0.4 0.4 0.6 1.5 3.1

0.4 0.4 0.7 1.9 3.9

0.5 0.5 0.9 2.3 4.9

0.5 0.7 1.5 3.7 7.9

0.4 0.3 0.4 1.1 2.2

6 7 8 9 10

C N O F Ne

0.42 0.60 0.80 1.00 1.41

0.50 0.83 1.45 1.9 2.6

4.6 7.5 12.9 16.5 22.8

5.7 9.3 15.8 20.3 27.9

7.1 11.5 19.5 25.2 34.6

8.8 14.4 24.5 31.4 43.1

14.2 23.1 39.4 50.3 69.0

4.1 6.7 11.4 14.6 20.1

11 12 13 14 15

Na Mg Al Si P

1.75 2.27 2.74 3.44 4.20

3.5 4.6 5.8 7.3 8.8

30.3 39.5 49.6 61.4 74.7

37.2 48.4 60.7 75.2 91.4

45.9 59.8 75.0 92.8 112.9

57.2 74.6 93.4 115.5 140.5

91.4 119.1 149.0 183.8 223.6

26.8 34.9 43.9 54.4 66.2

16 17 18 19 20

S Cl Ar K Ca

5.15 5.86 6.40 8.0 9.7

10.6 12.4 14.5 16.7 18.9

89.2 104.8 121.4 139.8 158.6

109.2 128.2 148.5 171 194

134.7 158.1 183.0 211 239

167.4 196.6 227.3 262 296

266.1 312.4 360.7 415 469

79.1 92.8 107.6 124 141

21 22 23 24 25

Sc Ti V Cr Mn

10.5 11.8 13.3 15.7 17.4

21.8 25.3 27.7 31.0 34.5

180.5 203 228 254 282

221 247 278 311 344

272 304 342 382 423

337 378 424 474 63.5

534 597 77 88 101

160 180 202 226 250

26 27 28 29 30

Fe Co Ni Cu Zn

19.9 21.8 25.0 26.4 28.2

38.1 42.1 46.4 50.7 55.4

311 341 48.3 53.7 59.5

380 52.8 58.9 65.5 72.7

57.6 64.9 72.5 80.6 89.4

71.4 80.6 90.0 100.0 110.9

113 127 142 158 175

276 303 333 K 47.6 52.8

31 32 33 34 35

Ga Ge As Se Br

30.8 33.5 36.5 38.5 42.3

60.1 65.2 70.5 76.0 82.5

65.9 72.3 79.1 86.1 93.9

80.5 88.2 96.6 105.1 114.7

99.0 108.6 118.9 129.4 141.2

122.8 134.7 147 161 175

194 213 233 254 277

58.5 64.1 70.2 76.4 83.4

36 Kr 37 Rb 38 Sr

45.0 48 52

88.3 95 102

101.9 84 90

124.5 103 110

153.2 127 137

190 158 170

300 252 271

90.5 98 106

K

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TABLE 7.8 Mass Absorption Coefficients for K␣1 Lines and W L␣1 Line (Continued) Emitter ˚ wavelength, A

Ag K␣1 0.559

Mo K␣1 0.709

Cu K␣1 1.541

Ni K␣1 1.658

Co K␣1 1.789

Fe K␣1 1.936

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Cr K␣1 2.290

W L␣1 1.476

Absorber 39 Y 40 Zr

56 61

109 17

97 104

119 128

147 158

183 197

292 314

114 122

41 42 43 44 45

Nb Mo Tc Ru Rh

66 71 76 K 12 13

18 19 20 22 23

112 119 128 137 146

138 146 157 168 179

170 180 194 207 221

212 225 241 258 275

338 358 384 410 438

132 140 150 160 171

46 47 48 49 50

Pd Ag Cd In Sn

14 15 15 16 17

24 26 28 30 32

155 165 174 185 195

190 202 213 227 239

235 249 263 280 295

292 310 327 347 367

466 493 520 553 583

182 193 204 217 229

51 52 53 54 55

Sb Te I Xe Cs

19 19 21 22 24

34 36 37 39 42

206 216 230 239 332

252 265 281 293 404

310 326 346 361 495

386 405 431 448 612

612 644 684 710 822

241 253 269 280 295

56 57 58 59 60

Ba La Ce Pr Nd

25 26 28 29 31

44 46 48 51 54

349 365 383 401 420

425 444 466 487 510

522 545 571 597 534

645 673 603 453 473

622 647 216 229 241

311 325 341 356 373

61 62 63 64 65

Pm Sm Eu Gd Tb

32 33 35 36 38

56 59 61 64 67

440 456 405 424 LII 316

535 473 354 370 135

417 148 156 164

164 173 182 191 201

254 268 282 296 311

392 406 423

66 67 68 69 70

Dy Ho Er Tm Yb

39 41 43 45 46

70 72 75 79 82

329 123 129 135 141

141 148 156 163 171

172 181 189 199 208

211 222 233 244 256

327 343 360 377 395

L 293 II 304 316 L 120 III 126

71 72 73 74 75

Lu Hf Ta W Re

48 51 52 55 57

84 88 91 95 98

148 155 162 169 176

179 187 196 204 213

218 228 238 249 260

267 280 293 306 319

414 433 453 473 494

132 138 144 151 157

76 Os 77 Ir 78 Pt

59 61 64

102 106 109

184 192 200

223 232 242

271 283 295

333 347 362

515 538 560

164 171 179

LI

LIII

393

LI

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TABLE 7.8 Mass Absorption Coefficients for K␣1 Lines and W L␣1 Line (Continued) Emitter ˚ wavelength, A

Ag K␣1 0.559

Mo K␣1 0.709

Cu K␣1 1.541

Ni K␣1 1.658

Co K␣1 1.789

Fe K␣1 1.936

Cr K␣1 2.290

W L␣1 1.476

Absorber 79 Au 80 Hg

67 69

113 117

209 218

252 263

307 321

377 394

584 609

186 194

81 82 83 84 85

Tl Pb Bi Po At

72 74 78

121 125 129 131

227 236 247 258 269

275 286 298 311 325

334 348 363 380 397

411 428 446 466 487

635 662 690 721 753

203 211 220 230 240

86 87 88 89 90

Rn Fr Ra Ac Th

85

281 294 307 322 337

340 356 372 389 408

414 433 453 474 497

509 532 556 582 610

787 823 861 900 944

251 262 274 287 301

91 92 93 94

Pa U Np Pu

353 372 392 418

427 450 474 505

520 548 578 615

639 673 709 755

988 898 945 835

315 332 350 373

7.2

89 91 97

104 54

ULTRAVIOLET-VISIBLE SPECTROSCOPY

Molecules with two or more isolated chromophores (absorbing groups) absorb light of nearly the same wavelength as does a molecule containing only a single chromophore of a particular type. The intensity of the absorption is proportional to the number of that type of chromophore present in the molecule. Representative chromophores are given in Table 7.9. The solvent chosen must dissolve the sample, yet be relatively transparent in the spectral region of interest. In order to avoid poor resolution and difficulties in spectrum interpretation, a solvent should not be employed for measurements that are near the wavelength of or are shorter than the wavelength of its ultraviolet cutoff, that is, the wavelength at which absorbance for the solvent alone approaches one absorbance unit. Ultraviolet cutoffs for solvents commonly used are given in Table 7.10. Appreciable interaction between chromophores does not occur unless they are linked directly to each other, or forced into close proximity as a result of molecular stereochemical configuration. Interposition of a single methylene group, or meta orientation about an aromatic ring, is sufficient to insulate chromophores almost completely from each other. Certain combinations of functional groups afford chromophoric systems which give rise to characteristic absorption bands. Sets of empirical rules, often referred to as Woodward’s rules or the Woodward-Fieser rules, enable the absorption maxima of dienes (Table 7.11) and enones and dienones (Table 7.12) to be predicted. To the respective base values (absorption wavelength of parent compound) are added the increments for the structural features or substituent groups present. When necessary, a solvent correction is also applied (Table 7.13).

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TABLE 7.9 Electronic Absorption Bands for Representative Chromophores Chromophore

System

Acetylide Aldehyde

9C#C9 9 CHO

Amine Azido Azo Bromide Carbonyl

9 NH2 C"N9 9N"N9 9 Br C"O

Carboxyl Disulfide

9 COOH 9S9S9

Ester Ether Ethylene Iodide Nitrate Nitrile Nitrite

9 COOR 9O9 9C"C9 9I 9 ONO2 9C#N 9 ONO

Nitro Nitroso Oxime Sulfone Sulfoxide Thiocarbonyl Thioether

9 NO2 9 NO 9 NOH 9 SO2 9 S"O C"S 9S9

Thiol

9 SH 9 (C " C)2 9 (acyclic) 9 (C " C)3 9 9 (C " C)4 9 9 (C " C)5 9 9 (C " C)2 9 (alicyclic) C"C9C#C C"C9C"N C"C9C"O C " C 9 NO2

Benzene

Diphenyl Naphthalene

Anthracene Phenanthrene Naphthacene

␭max 175– 180 210 280– 300 195 190 285– 400 208 195 270– 285 200– 210 194 255 205 185 190 260 270 (shoulder) 160 220– 230 300– 400 210 302 190 180 210 205 194 215 195 210– 230 260 300 330 230– 260 219 220 210– 250 300– 350 229 184 204 255 246 222 275 312 252 375 251 292 272 473

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⑀max 6 000 strong 11– 18 2 800 5 000 3– 25 300 1 000 18– 30 50– 70 5 500 400 50 1 000 8 000 400 12 1 000– 2 000 10 strong 100 5 000 1 500 strong 4 600 1 600 1 400 21 000 35 000 52 000 118 000 3 000– 8 000 6 500 23 000 10 000– 20 000 weak 9 500 46 700 6 900 170 20 000 112 000 5 600 175 199 000 7 900 66 000 14 000 180 000 12 500

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TABLE 7.9 Electronic Absorption Bands for Representative Chromophores (Continued) Chromophore

System

Pentacene

␭max 310 585 174 195 257 227 270 314 218 266 317

Pyridine

Quinoline

Isoquinoline

⑀max 300 12 80 6 1 37 3 2 80 4 3

000 000 000 000 700 000 600 750 000 000 500

TABLE 7.10 Ultraviolet Cutoffs of Spectrograde Solvents Absorbance of 1.00 in a 10.0 mm cell vs. distilled water.

Solvent Acetic acid Acetone Acetonitrile Benzene 1-Butanol 2-Butanol Butyl acetate Carbon disulfide Carbon tetrachloride 1-Chlorobutane Chloroform (stabilized with ethanol) Cyclohexane 1,2-Dichloroethane Diethyl ether 1,2-Dimethoxyethane N,N-Dimethylacetamide N,N-Dimethylformamide Dimethylsulfoxide 1,4-Dioxane Ethanol 2-Ethoxyethanol Ethyl acetate Ethylene chloride Glycerol Heptane

Wavelength, nm 260 330 190 280 210 260 254 380 265 220 245 210 226 218 240 268 270 265 215 210 210 255 228 207 197

Solvent Hexadecane Hexane Isobutyl alcohol Methanol 2-Methoxyethanol Methylcyclohexane Methylene chloride Methyl ethyl ketone Methyl isobutyl ketone 2-Methyl-1-propanol N-Methylpyrrolidone Nitromethane Pentane Pentyl acetate 1-Propanol 2-Propanol Pyridine Tetrachloroethylene (stabilized with thymol) Tetrahydrofuran Toluene 1,1,2-Trichloro-1,2,2trifluoroethane 2,2,4-Trimethylpentane o-Xylene Water

Wavelength, nm 200 210 230 210 210 210 235 330 335 230 285 380 210 212 210 210 330 290 220 286 231 215 290 191

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TABLE 7.11 Absorption Wavelength of Dienes Heteroannular and acyclic dienes usually display molar absorptivities in the 8000 to 20 000 range, whereas homoannular dienes are in the 5000 to 8000 range. Poor correlations are obtained for cross-conjugated polyene systems such as

The correlations presented here are sometimes referred to as Woodward’s rules or the Woodward-Fieser rules. Base value for heteroannular or open chain diene, nm Base value for homoannular diene, nm Increment (in nm) for double bond extending conjugation Alkyl substituent or ring residue Exocyclic double bond Polar groupings: -O-acyl -O-alkyl -S-alkyl -Cl, -Br -N (alkyl)2 Solvent correction (see Table 7.13)

214 253 30 5 5 0 6 30 5 60 Calculated wavelength ⫽

total

Ring substitution on the benzene ring affords shifts to longer wavelengths (Table 7.14) and intensification of the spectrum. With electron-withdrawing substituents, practically no change in the maximum position is observed. The spectra of heteroaromatics are related to their isocyclic analogs, but only in the crudest way. As with benzene, the magnitude of substituent shifts can be estimated, but tautomeric possibilities may invalidate the empirical method. When electronically complementary groups are situated para to each other in disubstituted benzenes, there is a more pronounced shift to a longer wavelength than would be expected from the additive effect due to the extension of the chromophore from the electron-donating group through the ring to the electron-withdrawing group. When the para groups are not complementary, or when the groups are situated ortho or meta to each other, disubstituted benzenes show a more or less additive effect of the two substituents on the wavelength maximum. Calculation of the principal band of selected substituted benzenes is illustrated in Table 7.15.

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TABLE 7.12 Absorption Wavelength of Enones and Dienones

Base values, nm Acyclic ␣,␤-unsaturated ketones Acyclic ␣,␤-unsaturated aldehyde Six-membered cyclic ␣,␤-unsaturated ketones Five-membered cyclic ␣,␤-unsaturated ketones ␣,␤-Unsaturated carboxylic acids and esters Increments (in nm) for Double bond extending conjugation: Heteroannular Homoannular Alkyl group or ring residue: ␣ ␤ ␥, ␦ Polar groups: 9 OH ␣ ␤ ␥ 9 O 9 CO 9 CH3 and 9 O 9 CO 9 C6H5: ␣, ␤, ␥, ␦ 9 OCH3 ␣ ␤ ␥ ␦ 9 S 9 alkyl, ␤ 9 Cl ␣ ␤ 9 Br ␣ ␤ 9 N(alkyl)2, ␤ Exocyclic double bond Solvent correction (see Table 7.13) Calculated wavelength ⫽

215 210 215 214 195

30 69 10 12 18

35 30 50 6 35 30 17 31 85 15 12 25 30 95 5 total

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TABLE 7.13 Solvent Correction for UltravioletVisible Spectroscopy Solvent

Correction, nm

Chloroform Cyclohexane Diethyl ether 1,4-Dioxane Ethanol Hexane Methanol Water

⫹1

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⫹11 ⫹5 0 ⫹11 0 ⫺8

TABLE 7.14 Primary Bands of Substituted Benzene and Heteroaromatics In methanol. Base value: 203.5 nm.

Substituent 9 CH3 9 CH " CH2 9 C # CH 9 C6H5 9F 9 Cl 9 Br 9I 9 OH 9 O⫺ 9 OCH3 9 OC6H5 9 CHO 9 CO 9 CH3 9 CO 9 C6H5

Heteroaromatic Furan Pyrazine Pyrazole Pyridazine

Wavelength shift, nm 3.0 44.5 44 48 0 6.0 6.5 3.5 7.0 31.5 13.5 51.5 46.0 42.0 48

Base value, nm 200 257 214 ca 240

Substituent 9 COOH 9 COO⫺ 9 CN 9 NH2 9 NH ⫹3 9 N(CH3)2 9 NH 9 CO 9 CH3 9 NO2 9 SH 9 SO 9 C6H5 9 SO2CH3 9 SO2NH2 9 CH " CH 9 C6H5 cis trans 9 CH " CH 9 COOH, trans

Heteroaromatic Pyridine Pyrimidine Pyrrole Thiophene

Wavelength shift, nm 25.5 20.5 20.5 26.5 ⫺0.5 47.0 38.5 57 32 28 13 14.0 79 92.0 69.5 Base value, nm 257 ca 235 209 231

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TABLE 7.15 Wavelength Calculation of the Principal Band of Substituted Benzene Derivatives

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In ethanol. Base value of parent chromophore, nm C6H5COOH or C6H5COO 9 alkyl C6H5 9 CO 9 alkyl (or aryl) C6H5CHO Increment (in nm) for each substituent on phenyl ring 9 Alkyl or ring residue o-, mp9 OH and 9 O 9 alkyl o-, mp9 O⫺ omp9 Cl o-, mp9 Br o-, mp9 NH2 o-, mp9 NHCO 9 CH3 o-, mp9 NHCH3 p9 N(CH3)2 o-, mp-

230 246 250

3 10 7 25 11 20 78* 0 10 2 15 13 58 20 45 73 20 85

* Value may be decreased markedly by steric hindrance to coplanarity.

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FLUORESCENCE

TABLE 7.16 Fluorescence Spectroscopy of Some Organic Compounds

Compound Acenaphthene Acridine Adenine Adenosine Adenosine triphosphate Adrenalin p-Aminobenzoic acid Aminopterin 1-Aminopyrene p-Aminosalicyclic acid Amobarbital Anilines Anthracene Anthranilic acid Azaindoles Benz[c]acridine Benz[a]anthracene 1,2-Benzanthracene Benzanthrone Benzo[b]chrysene 11-H-Benzo[a]fluorene Benzoic acid 3,4-Benzopyrene Benzo[e]pyrene Benzoquinoline Benzoxanthane Bromolysergic acid diethyl amide Brucine Carbazole Chlortetracycline Chrysene

Solvent Pentane CF3COOH Water Water Water Water Water CF3COOH Water Water Water Pentane Water Water CF3COOH Pentane

pH

1 1 1 8 7 11 14 7 7 10

CF3COOH Pentane Pentane 70% H2SO4 Benzene Pentane CF3COOH Pentane Water Water N,N-Dimethyl formamide

1 7

Pentane

Cinchonine Coumarin Dibenzo[a,c]anthracene Dibenzo[b,k]chrysene Dibenzo[a,e]pyrene 3,4,8,9-Dibenzopyrene

Water Ethanol Pentane Pentane Pentane

5,12-Dihydronaphthacene 1,4-Diphenylbutadiene Epinephrine Ethacridine Fluoranthrene Fluorene Fluorescein

Pentane Pentane Water Water Pentane Pentane Water

1

7 2

7– 11

Excitation wavelength, nm

Emission wavelength, nm

291 358 280 285 285 295 295 280, 370 330, 342 300 265 280, 291 420 300 290, 299 295, 380 284 280, 340 370, 420 283 317 285 365 329 280 363

341 475 375 395 395 335 345 460 415 405 410 344, 361 430 405 310, 347 480 382 390, 410 550 398 340 385 390, 480 389 425 418

315 305 291

460 500 359

355 250, 300, 310 320 280 280 308 370 370, 335, 390, 410 282 328 295 370, 425 354 300 490

445 260, 380 420 352 381 428 401 480, 510 340 370 335 515 464 321 515

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TABLE 7.16 Fluorescence Spectroscopy of Some Organic Compounds (Continued)

Compound

Solvent

pH

Folic acid Gentisic acid Griseofulvin Guanine Harmine Hippuric acid Homovanillic acid m-Hydroxybenzoic acid p-Hydroxycinnamic acid 7-Hydroxycoumarin 5-Hydroxyindole 5-Hydroxyindoleacetic acid 3-Hydroxykynurenine p-Hydroxymandelic acid p-Hydroxyphenylacetic acid p-Hydroxyphenylpyruvic acid p-Hydroxyphenylserine 5-Hydroxytryptophan Imipramine Indoleacetic acid Indoles Indomethacin Kynurenic acid

Water Water Water Water Water 70% H2SO4 Water Water Water Ethanol Water Water Water Water Water Water Water Water Water Water Water Water Water

7 7 7 1 1

Lysergic acid diethylamide Menadione 9-Methylanthracene 3-Methylcholanthrene 7-Methyldibenzopyrene 2-Methylphenanthrene 3-Methylphenanthrene 1-Methylpyrene 4-Methylpyrene Naphthacene 1-Naphthol

Water Ethanol Pentane Pentane Pentane Pentane Pentane Pentane Pentane

2-Naphthol Oxytetracycline Phenanthrene Phenylalanine o-Phenylenepyrene Phenylephrine Picene Procaine Pyrene Pyridoxal Quinacrine Quinidine Quinine Reserpine

7 12 7 1 7 11 7 7 7 1 7 14 8 7 13 7 11 1

0.1 M NaOH 20% ethanol 0.1 M NaOH 20% ethanol Pentane Water Pentane Pentane Water Pentane Water Water Water Water Water

11 12 11 1 1 1

Excitation wavelength, nm

Emission wavelength, nm

365 315 295, 335 285 300, 365 270 270 314 350 325 290 300 365 300 280 290 290 295 295 285 269, 315 300 325 325 325 335 382 297 460 257 292 336 338 290, 310 365

450 440 450 365 400 370 315 430 440 441 355 355 460 380 310 345 320 340 415 360 355 410 405 440 445 480 410 392 467 357 368 394 386 480, 515 480

365

426

390 252 215, 260 360 270 281 275 330 310 285 350 250, 350 300

520 362 282 506 305 398 345 382 365 420 450 450 375

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TABLE 7.16 Fluorescence Spectroscopy of Some Organic Compounds (Continued)

Compound

Solvent

Resorcinol Riboflavin

Water Water

Rutin Salicyclic acid Scoparone Scopoletin Serotonin Skatole Streptomycin p-Terphenyl Thiopental Thymol Tocopherol Tribenzo[a,e,i]pyrene Triphenylene Tryptamine Tryptophan Tyramine Tyrosine Uric acid Vitamin A Vitamin B12 Warfarin Xanthine 2,6-Xylenol 3,4-Xylenol Yohimbine Zoxazolamine

Water Water Water Water 3M HCl Water Water Pentane

pH

7 1 11 10 10

13

Water Hexane-ethanol Pentane Pentane Water Water Water Water Water 1-Butanol Water Methanol Water

7

7 11 1 7 1

Water Water

1 11

7 1

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Excitation wavelength, nm

Emission wavelength, nm

265 270, 370, 445 430 310 350, 365 365, 390 295 290 366 284 315 265 295 384 288 290 285 275 275 325 340 275 290, 342 315 275 280 270 280

315 520 520 435 430 460 550 370 445 338 530 300 340 448 357 360 365 310 310 370 490 305 385 435 305 310 360 320

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TABLE 7.17 Fluorescence Quantum Yield Values

Compound

Solvent

QF value vs. QF standard

QF standard 9-Aminoacridine Anthracene POPOP* Quinine sulfate dihydrate

Water Ethanol Toluene 1N H2SO4

0.99 0.30 0.85 0.55

Secondary standards Acridine orange hydrochloride

Ethanol

1,8-ANS† (free acid)

Ethanol

1,8-ANS (magnesium salt)

Ethanol

Fluorescein

0.1N NaOH

Fluorescein, ethyl ester

0.1N NaOH

Rhodamine B

Ethanol

2,6-TNS‡ (potassium salt)

Ethanol

0.54 0.58 0.38 0.39 0.29 0.31 0.91 0.94 0.99 0.99 0.69 0.70 0.48 0.51

Quinine sulfate Anthracene Anthracene POPOP Anthracene POPOP Quinine sulfate POPOP Quinine sulfate POPOP Quinine sulfate Anthracene Anthracene POPOP

* POPOP p-bis[2-(5-phenyloxazoyl)]benzene. † ANS, anilino-8-naphthalene sulfonic acid. ‡ TNS, 2-p-toluidinylnaphthalene-6-sulfonate.

7.4

FLAME ATOMIC EMISSION, FLAME ATOMIC ABSORPTION, ELECTROTHERMAL (FURNACE) ATOMIC ABSORPTION, ARGON INDUCTION COUPLED PLASMA, AND PLASMA ATOMIC FLUORESCENCE

The tables of atomic emission and atomic absorption lines are presented in two parts. In Table 7.18 the data are arranged in alphabetic order by name of the element, whereas in Table 7.19 the sensitive lines of the elements are arranged in order of decreasing wavelengths. For additional lines and their relative intensities consult W. F. Meggers, C. H. Corliss, and B. F. Scribner, Tables of Spectral-Line Intensities, Part I, National Bureau of Standards Monograph 32, U.S. Government Printing Office, Washington, D.C., 1961. The detection limits in the table correspond generally to the concentration of an element required to give a net signal equal to three times the standard deviation of the noise (background) in accordance with IUPAC recommendations. Detection limits can be confusing when steady-state techniques such as flame atomic emission or absorption, and plasma atomic emission or fluorescence, which

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TABLE 7.18 Detection Limits in ng/mL The detection limits in the table correspond generally to the concentration of analyte required to give a net signal equal to three times the standard deviation of the background in accordance with IUPAC recommendations.

Element Aluminum

Antimony

Arsenic

Barium

Beryllium

Bismuth

Boron (as BO2) (as BO2) Bromine Cadmium

Calcium

Carbon Cerium

Cesium Chlorine Chromium

Wavelength, nm 308.22 309.28 394.40 396.15 206.83 217.58 231.15 259.81 189.04 193.76 197.20 228.81 234.90 455.36 493.41 553.55 234.86 313.04 313.11 223.06 227.66 306.77 182.59 249.77 518.0 547.6 154.07 214.44 226.50 228.80 326.11 315.89 393.37 396.85 422.67 193.09 247.86 413.38 418.66 569.92 852.11 894.35 134.72 267.72 283.58 284.98 357.87 359.35

Flame emission

3.6 7.5

Flame atomic absorption 40 20 45 30

Electrothermal atomic absorption

0.05 0.01

30 70 200

10 11 36 20 50 50 30

0.08 160 120 240

455 250 3 4 1.5

Argon ICP

1

Plasma atomic fluorescence

4 5

10 0.1

35 50

10 0.9 1 9 1 2

0.04 0.05 0.003

18

0.35 2 0.5

100

60 700

15

2 0.4 1 1 30 30 8 3

0.2

2 60

50 50

6 3

1 0.5

0.008 0.014

50 1.0 0.6 228 0.001 20 0.6 1.2

1.5

1

0.3

0.08 44 1000 30 30

150 0.02 0.04

8 130

0.04 50 3 20 30

6 7

2

0.05

0.4

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TABLE 7.18 Detection Limits in ng/mL (Continued)

Element Chromium (cont.)

Cobalt

Copper Dysprosium

Erbium

Europium

Gadolinium

Gallium

Germanium

Gold Hafnium

Holmium

Indium

Iodine Iridium

Wavelength, nm 360.53 425.44 427.48 428.97 228.62 238.89 240.73 345.35 324.75 327.40 353.17 340.78 404.60 418.68 421.17 323.06 349.81 400.80 408.77 381.97 412.97 459.40 335.05 368.41 440.19 287.42 294.36 404.30 417.21 209.43 219.87 265.12 242.80 267.60 263.87 277.34 307.29 339.90 345.60 405.39 410.38 230.61 303.94 325.61 410.18 451.13 178.38 183.0 208.88 212.68 224.27

Flame emission 13 3 4 5

5 30 1.5 3

30

Flame atomic absorption

Electrothermal atomic absorption

Argon ICP

6

66

8

0.01

3 28 7

1 2

0.01 0.02

2 4 3 6

50 60 60

Plasma atomic fluorescence

0.4 0.2

300

15 10 30

40 40

0.3

500 2 3

0.45

20

0.5

20 10

72

5 3

400 500

4000 1000 70 20 50 30

40 10 8

8

800 30

1

7.5 0.5 0.5

40 50 100

0.9

50 5 10 10 10

0.3

2000 3 8 15

40 30

0.7

100 22 14 0.7

7 8 20 22

0.01

100 40

400

500

2 20

0.2

3 0.5 20 20

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TABLE 7.18 Detection Limits in ng/mL (Continued)

Element Iron

Lanthanum

(as LaO) (as LaO) Lead

Lithium

Lutetium Magnesium

Manganese

Mercury Molybdenum

Neodymium

Nickel

Niobium

Wavelength, nm 238.20 248.33 259.94 302.06 371.99 385.99 379.48 392.76 408.67 550.13 579.13 441.82 560.25 217.10 220.35 283.31 368.35 405.78 460.29 610.36 670.78 261.54 307.76 279.08 279.55 285.21 256.37 257.61 259.37 260.57 279.48 293.30 294.92 403.08 194.23 253.65 202.03 203.84 281.62 313.26 390.30 292.45 401.23 430.36 492.45 231.60 232.00 341.48 352.45 316.34 405.89

Flame emission

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Flame atomic absorption

Electrothermal atomic absorption

3

0.01

Argon ICP

Plasma atomic fluorescence

4 3 18 15 12

5 10 21

0.3 15

8000 2 20 5 100 300

2000

0.5

20

0.4

10

1

20 60 30 20 0.06 0.001 0.003

4.5

30

50

0.3

1.5

0.1

0.018

60 1

1

5

5 1 6 30 1.5 3.6 2.7 0.5 3 6

0.05

0.4

0.4

0.4 24 24

1.5 150

220 75 200

30 0.001

30 50

6

30 50 5 8 1.2

0.06

5

12

10 30 150 8 15 8

600 4 2 2

2000 0.5

6 10 2 20

250

1000

1000

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TABLE 7.18 Detection Limits in ng/mL (Continued)

Element Osmium

Palladium

Phosphorus (as HPO) Platinum Potassium

Praseodymium

Rhenium

Rhodium Rubidium Ruthenium Samarium Scandium

Selenium Silicon Silver Sodium

Strontium

Sulfur (as S2)

Wavelength, nm 225.58 228.23 263.71 290.91 244.8 340.46 363.47 178.28 213.62 524.9 214.42 265.95 404.41 404.72 766.49 769.90 390.84 414.31 493.97 197.31 345.19 346.05 346.47 343.49 369.24 780.02 794.76 240.27 349.89 442.43 476.03 255.24 357.24 361.38 391.18 402.04 402.34 196.03 251.61 283.16 328.07 338.29 330.23 330.30 589.00 589.59 407.78 421.55 460.73 180.73 394.0

Flame emission

Flame atomic absorption

Electrothermal atomic absorption

Argon ICP

Plasma atomic fluorescence

20 40 2000 20 25 50

80 110 20 80

0.5

40 40 60 50 50

100 2000 1.3 2.6 0.15 0.3

100 100 1 2

0.2

0.004

20 40

200

300

0.6

20 30 300

1000 8

690 200 275 10 20 0.0065 0.013

200 2

10 0.1

0.3

80

70

30

500

21 30 30

20

6

90 80

2.5 0.5

2 4 125 250 0.01 0.02

0.9

0.2

10

20 30 500 50 150 10 100 21 1 1.5 120

0.7

6 10 15 4.5 3 15

0.004

20

0.001

100 3

500

10

10 50 0.1

0.2

1 0.5 0.1 1600

2 10

0.01

0.3 70

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TABLE 7.18 Detection Limits in ng/mL (Continued)

Element Tantalum Tellurium Terbium

Thallium

Thorium Thulium

Tin

Titanium

Tungsten

Uranium

Vanadium

Ytterbium

Yttrium

Zinc Zirconium

Wavelength, nm 240.06 271.47 214.27 238.58 350.92 384.87 431.89 190.86 276.78 351.92 377.57 535.0 283.73 401.91 313.13 371.79 384.80 189.99 224.60 284.00 286.33 334.19 334.94 337.28 364.27 365.35 399.86 207.91 209.48 400.87 358.49 385.96 409.01 292.40 310.23 318.34 318.54 437.92 328.94 369.42 398.80 360.07 362.09 371.03 410.24 202.55 213.86 339.20 343.82 349.62 360.12

Flame emission

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Flame atomic absorption

Electrothermal atomic absorption

Argon ICP

Plasma atomic fluorescence

20 150

800 15

0.5

2 60 10 40

150

600

500 50

9

0.15 150

3 1.5

0.5

4 30 30 3

4

100

10

110 200 160

100

1

7 15 30 10

1.5

400 6 8 210 180 150

60

2.5

30

30 50 450 100

1000

2000 30 70 140 7.8 10

18 25 15

50

1

30 1 2

0.45

5

0.1

10 3

40

50

10

50 1

30 1000

1000

50 0.8

350

0.005

4 2 5 7 45

0.0003

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TABLE 7.19 Sensitive Lines of the Elements In this table the sensitive lines of the elements are arranged in order of decreasing wavelengths. A Roman numeral II following an element designation indicates a line classified as being emitted by the singly ionized atom. In the column headed Sensitivity, the most sensitive line of the non-ionized atom is indicated by U1, and other lines by U2, U3, and so on, in order of decreasing sensitivity. For the singly ionized atom the corresponding designations are V1, V2, V3, and so on. Wavelength, nm 894.35 852.11 819.48 818.33 811.53 794.76 780.02 769.90 766.49 750.04 706.72 696.53 690.24 685.60 670.78 656.28 649.69 624.99 614.17 610.36 593.06 589.59 589.00 587.76 587.09 579.13 569.92 567.96 567.60 566.66 557.02 553.55 550.13 546.55 546.07 545.52 535.84 535.05 521.82 520.91 520.84 520.60 515.32 498.18 496.23 493.97 493.41

Element Cs Cs Na Na Ar Rb Rb K K Ar Ar Ar F F Li H Ba La Ba Li La Na Na He Kr La Ce N N N Kr Ba La Ag Hg La Hg Tl Cu Ag Cr Cr Cu Ti Sr Pr Ba

II II

II II II

II

Sensitivity

Wavelength, nm

U2 U1 U4 U3 U2 U2 U1 U2 U1 U4 U3 U3 U3 U2 U1 U2 V4 U3 V3 U2 U4 U2 U1 U3 U2 U1 U1 V2 V4 V3 U3 U1 U2 U4 U2 U3 U3 U1 U3 U3 U8 U7 U4 U1 U2 U1 V2

492.45 488.91 487.25 483.21 482.59 481.95 481.67 481.05 481.01 479.45 478.55 476.03 470.09 467.12 462.43 460.73 460.29 459.40 459.32 455.54 455.40 451.13 450.10 445.48 442.43 440.85 440.19 439.00 437.49 437.92 435.84 431.89 430.36 430.21 429.67 428.97 427.48 425.43 422.67 421.56 421.55 421.17 420.19 418.68 418.66 417.21 414.31

Element Nd Re Sr Sr Ra Cl Br Zn Cl Cl Br Sm Br Xe Xe Sr Li Eu Cs Cs Ba In Xe Ca Sm V Gd V Y V Hg Tb Nd W Sm Cr Cr Cr Ca Rb Sr Dy Rb Dy Ce Ga Pr

II II II II II II

II

II

II

II

II

II II

Sensitivity U1 U4 U3 U2 U1 V4 V3 U3 V3 V2 V2 U1 V1 U2 U3 U1 U4 U1 U4 U3 V1 U1 U4 U2 V4 U4 U1 U3 V4 U1 U3 U1 V2 U1 U1 U3 U2 U1 U1 U4 V1 U2 U3 U2 V1 U1 V2

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TABLE 7.19 Sensitive Lines of the Elements (Continued) Wavelength, nm 414.29 413.38 413.07 412.97 412.83 412.38 412.32 411.00 410.38 410.24 410.18 410.09 409.99 409.01 408.77 408.67 407.97 407.77 407.74 407.74 407.43 405.89 405.78 405.39 404.72 404.66 404.60 404.41 403.45 403.31 403.30 403.08 402.37 402.04 401.91 401.23 400.87 400.80 399.86 399.86 398.80 396.85 396.15 394.91 394.40 393.37 391.18 390.84 390.75 390.30 389.18 388.86 388.63

Element Y Ce Ba Eu Y Nb La N Ho Y In Nb N U Er La Nb Sr Y La W Nb Pb Ho K Hg Dy K Mn Mn Ga Mn Sc Sc Th Nd W Er Cr Ti Yb Ca Al La Al Ca Sc Pr Sc Mo Ba He Fe

II II II

II

II II II II

II II

II II II II

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Sensitivity

Wavelength, nm

U4 V1 V5 V2 U3 U4 V4 U2 U1 U1 U2 U3 U3 V2 U1 V1 U2 V2 U2 V2 U2 U1 U1 U2 U4 U5 U1 U3 U3 U2 U2 U1 U3 U3 V1 V1 U1 U1 U1 U1 U1 V2 U1 V2 U2 V1 U1 V1 U2 U1 V4 U2 U5

386.41 385.99 385.96 384.87 384.80 383.83 383.82 382.23 382.94 381.97 379.94 379.63 379.48 379.08 377.57 377.43 374.83 373.49 372.80 371.99 371.79 371.03 369.42 369.24 368.41 368.35 365.48 365.35 365.01 364.28 364.27 363.47 363.07 362.09 361.38 360.96 360.12 360.07 360.05 359.62 359.34 359.26 358.49 357.87 357.25 357.24 356.83 355.31 354.77 353.17 352.98 352.94 352.69

Element Mo Fe U Tb Tm Mg Mo Mg Mg Eu Ru Mo La La Tl Y Fe Fe Ru Fe Tm Y Yb Rh Gd Pb Hg Ti Hg Sc Sn Pd Sc Y Sc Pd Zr Y Cr Ru Cr Sm U Cr Zr Sc Sn Pd Zr Dy Co Tl Co

II II II

II

II II II

II II

II

II II

II

II

II II II

II

Sensitivity U2 U2 V1 V2 V2 U2 U2 U3 U4 V1 U3 U1 V2 V3 U3 V3 U4 U2 U1 U1 U1 V1 V2 U2 U2 U2 U4 U2 U3 V3 U3 U2 V2 U2 V1 U2 U1 V2 U6 U3 U5 V1 V1 U4 V4 V1 V1 U3 U3 V1 U3 U4 U4

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TABLE 7.19 Sensitive Lines of the Elements (Continued) Wavelength, nm 352.45 351.96 351.92 351.69 351.36 350.92 350.63 350.23 349.89 349.62 349.41 348.11 347.40 346.47 346.05 345.60 345.58 345.19 345.14 344.36 344.06 343.82 343.67 343.49 342.83 342.12 341.48 341.23 340.78 340.51 340.46 339.90 339.20 338.29 337.28 336.12 335.05 334.94 334.50 334.19 332.11 331.12 330.03 330.26 330.23 328.94 328.23 328.07 327.40 326.95 326.23 326.11 325.61

Element Ni Zr Tl Pd Ir Tb Co Co Ru Zr Er Pd Ni Re Re Ho Co Re B Co Fe Zr Ru Rh Ru Pd Ni Co Dy Co Pd Ho Zr Ag Ti Ti Gd Ti Zn Ti Be Ta Na Zn Na Yb Zn Ag Cu Ge Sn Cd In

II

II II

II

II

II

II

II II II II II II

II

Sensitivity

Wavelength, nm

U2 U3 U2 U3 U2 V1 U3 U2 U2 V3 V1 U5 U3 U2 U1 V2 U5 U3 V2 U2 U2 V2 U2 U1 U4 U3 U3 U4 V2 U2 U2 V1 V1 U2 V3 V2 V1 V1 U2 U4 U3 U3 U6 U3 U5 V1 U5 U1 U2 U3 U3 U1 U3

324.75 324.27 323.45 323.26 323.06 322.08 318.54 318.40 317.93 316.34 315.89 313.26 313.13 313.11 313.04 311.84 311.07 310.23 309.42 309.31 309.27 308.22 307.76 307.29 306.77 306.47 303.94 303.90 303.41 302.06 300.91 294.91 294.44 294.36 294.02 293.30 292.98 292.45 292.40 290.91 289.80 289.10 288.16 287.42 287.15 286.33 286.04 285.21 284.82 284.00 283.73 283.58 283.31

Element Cu Pd Cr Li Er Ir V V Ca Nb Ca Mo Tm Be Be V V V Nb V Al Al Lu Hf Bi Pt In Ge Sn Fe Sn Mn W Ga Ta Mn Pt Nd V Os Bi Mo Si Ga Mo Sn As Mg Mo Sn Th Cr Pb

II

II II II II

II II II II II

II

II

II

II

II

II

II II II

Sensitivity U1 U4 V3 U3 V2 U1 U3 U2 V3 V1 V4 U2 V1 U1 U2 V4 V3 V2 V1 V1 U3 U4 V2 U1 U3 U1 U4 U2 U3 U3 U4 V4 U5 U3 U3 V4 U3 U2 V1 U2 U2 V4 U1 U4 V3 U2 U2 U1 V2 U1 V1 V2 U3

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TABLE 7.19 Sensitive Lines of the Elements (Continued) Wavelength, nm 283.16 283.03 281.62 281.61 280.27 280.20 279.83 279.55 279.48 279.08 278.02 277.34 276.78 272.44 271.90 271.47 270.65 267.72 267.60 266.92 265.95 265.12 265.05 264.75 263.87 263.71 260.57 259.94 259.81 259.37 257.61 256.37 255.33 255.24 253.65 253.57 252.85 252.29 251.61 250.69 250.20 249.77 249.68 248.33 247.86 245.65 243.78 242.80 241.05 240.73 240.49 240.27 240.06

Element Si Pt Al Mo Mg Pb Mn Mg Mn Mg As Hf Tl W Fe Ta Sn Cr Au Al Pt Ge Ba Ta Hf Os Mn Fe Sb Mn Mn Mn P Sc Hg P Si Fe Si Si Zn B B Fe C As Ag Au Fe Co Fe Ru Ta

II II II II

II II II

II II

II II II

II II II

II

II II

II

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Wavelength, nm

V1 U3 V2 V1 V2 U4 U3 V1 U3 V2 U1 V1 U4 U4 U5 U1 U4 V1 U2 V1 U1 U1 U2 U2 V1 U1 V3 V1 U2 U2 V1 V2 U3 V3 U1 U1 U2 U3 U3 U4 V4 U1 U2 U3 U2 U4 V2 U1 V4 U1 V3 V1 V1

239.56 238.89 238.58 238.32 238.20 234.90 234.86 232.00 231.60 231.15 230.61 228.81 228.80 228.71 228.62 228.23 227.66 227.02 226.50 226.45 225.58 225.39 224.70 224.64 224.60 224.27 223.06 220.35 219.87 219.23 217.58 217.00 214.44 214.42 214.27 213.86 213.62 213.60 212.68 209.48 209.43 208.88 207.91 207.48 206.83 206.28 206.19 203.99 203.84 202.55 202.03 197.31 197.20

Element Fe Co Te Te Fe As Be Ni Ni Sb In As Cd Ni Co Os Bi Ni Cd Ni Os Ni Cu Ag Sn Ir Bi Pb Ge Cu Sb Pb Cd Pt Te Zn P Cu Ir W Ge Ir W Se Sb Se Zn Se Mo Zn Mo Re As

II II

II

II II

II II II II II II II II II II II II II II II II II

II II II II II

II II II II II

Sensitivity V2 V2 U2 U3 V1 U4 U1 U2 V1 U1 V1 U5 U2 V1 V1 V2 U3 V2 V2 V3 V1 V4 V3 V3 U1 V1 U1 V1 V2 V2 U2 V1 V1 V1 U1 U1 U1 V1 V1 V2 V1 U1 V1 U4 U1 U3 V2 U1 V3 V1 V2 V1 U3

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TABLE 7.19 Sensitive Lines of the Elements (Continued) Wavelength, nm

Element

Sensitivity

Wavelength, nm

196.03 194.23 193.76 193.09 190.86 189.99 189.04

Se Hg II As C Tl II Sn II As

U2 V1 U1 U1 V1 V1 U2

183.00 182.59 180.73 178.38 178.28 154.07 134.72

Element I B S I P Br Cl

II

II II

Sensitivity U2 V2 U1 U1 U1 V4 V1

are steady-state techniques, are compared with the electrothermal or furnace technique which uses the entire sample and detects an absolute amount of the analyte element. To compare the several methods on the basis of concentration, the furnace detection limits assume a 20-␮L sample. Data for the several flame methods assume an acetylene–nitrous oxide flame residing on a 5- or 10-cm slot burner. The sample is nebulized into a spray chamber placed immediately ahead of the burner. Detection limits are quite dependent on instrument and operating variables, particularly the detector, the fuel and oxidant gases, the slit width, and the method used for background correction and data smoothing.

7.4.1

Some Common Spectroscopic Relationships

7.4.1.1 Electromagnetic Radiation. Electromagnetic radiation travels in straight lines in a uniform medium, has a velocity of 299 792 500 m · s⫺1 in a vacuum, and possesses properties of both a wave motion and a particle (photon). Wavelength ␭ is the distance from crest to crest; frequency v is the number of waves passing a fixed point in a unit length of time. Wavelength and frequency are related by the relation c ⫽ ␭v where c is the velocity of light (in a vacuum). In any material medium the speed of propagation is smaller than this and is given by the product nc, where n is the refractive index of the medium. Radiation is absorbed or emitted only in discrete packets called photons and quanta: E ⫽ hv where E is the energy of the quantum and h is Planck’s constant. The relation between energy and mass is given by the Einstein equation: ⌬E ⫽ ⌬mc2 where ⌬E is the energy release and ⌬m is the loss of mass. Strictly, the mass of a particle depends on its velocity, but here the masses are equated to their rest masses (at zero velocity). The Wien displacement law states that the wavelength of maximum emission, ␭m , of a blackbody varies inversely with absolute temperature; the product ␭mT remains constant. When ␭m is expressed in micrometers, the law becomes

␭mT ⫽ 2898

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In terms of ␴m , the wavenumber of maximum emission:

␴m ⫽ 3.48T Another useful version is hvm ⫽ 5kT, where k is the Boltzmann constant. Stefan’s law states that the total energy J radiated by a blackbody per unit time and area (power per unit area) varies as the fourth power of the absolute temperature: J ⫽ aT⫺4 where a is a constant whose value is 5.67 ⫻ 10⫺8 W · m⫺2 · K⫺4. The relationship between the voltage of an X-ray tube (or other energy source), in volts, and the wavelength is given by the Duane-Hunt equation:

␭⫽

hc 12 398 ⫽ eV V

where the wavelength is expressed in angstrom units. 7.4.1.2 Laws of Photometry. The time rate at which energy is transported in a beam of radiant energy is denoted by the symbol P0 for the incident beam, and by P for the quantity remaining unabsorbed after passage through a sample or container. The ratio of radiant power transmitted by the sample to the radiant power incident on the sample is the transmittance T: T⫽

P P0

The logarithm (base 10) of the reciprocal of the transmittance is the absorbance A:

冉冊 1 T

A ⫽ ⫺log T ⫽ log

When a beam of monochromatic light, previously rendered plane parallel, enters an absorbing medium at right angles to the plane-parallel surfaces of the medium, the rate of decrease in radiant power with the length of light path (cuvette interior) b, or with the concentration of absorbing material C (in grams per liter) will follow the exponential progression, often referred to as Beer’s law: T ⫽ 10⫺abC

or

A ⫽ abC

where a is the absorptivity of the component of interest in the solution. When C is expressed in moles per liter, T ⫽ 10⫺⑀bC

or

A ⫽ ⑀bC

where ⑀ is the molar absorptivity. The total fluorescence (or phosphorescence) intensity is proportional to the quanta of light absorbed, P0 ⫺ P, and to the efficiency ␾, which is the ratio of quanta absorbed to quanta emitted: F ⫽ (P0 ⫺ P)␾ ⫽ P0␾ (1 ⫺ e⫺⑀bC ) When the terms ⑀bC is not greater than 0.05 (or 0.01 in phosphorescence), F ⫽ k␾P0⑀bC

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where the term k has been introduced to handle instrumental artifacts and the geometry factor because fluorescence (and phosphorescence) is emitted in all directions but is viewed only through a limited aperture. The thickness of a transparent film or the path length of infrared absorption cells b, in centimeters, is given by b⫽

1 2nD

冉

n v¯ 1 ⫺ v¯ 2

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冊

where n is the number of fringes (peaks or troughs) between two wavenumbers v¯ 1 and v¯ 2 , and nD is the refractive index of the sample material (unity for the air path of an empty cuvette). If measurements are made in wavelength, as micrometers, the expression is b⫽

1 2nD

冉

n␭1␭2 ␭2 ⫺ ␭1

冊

7.4.1.3 Grating Equation. The light incident on each groove is diffracted or spread out over a range of angles, and in certain directions reinforcement or constructive interference occurs, as stated in the grating formula: m␭ ⫽ b(sin i ⫾ sin r) where b is the distance between adjacent grooves, i is the angle of incidence, r is the angle of reflection (both angles relative to the grating normal), and m is the order number. A positive sign applies where incoming and emergent beams are on the same side of the grating normal. The blaze wavelength is that wavelength for which the angle of reflectance from the groove face and the angle of reflection (usually the angle of incidence) from the grating are identical. The Bragg equation m␭ ⫽ 2d sin ␪ states the condition for reinforcement of reflection from a crystal lattice, where d is the distance between each set of atomic planes and ␪ is the angle of reflection. 7.4.1.4 Ionization of Metals in a Plasma. A loss in spectrochemical sensitivity results when a free metal atom is split into a positive ion and an electron: M ⫽ M⫹ ⫹ e⫺ The degree of ionization, ␣i , is defined as

␣i ⫽

[M⫹] [M ] ⫹ [M] ⫹

At equilibrium, when the ionization and recombination rates are balanced, the ionization constant Ki (in atm) is given by Ki ⫽

[M⫹][e⫺] ⫽ [M]

冉

␣ 2i 1 ⫺ ␣ 2i

冊

p⌺M

where p⌺M (in atm) is the total atom concentration of metal in all forms in the plasma.

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The ionization constant can be calculated from the Saha equation: log Ki ⫽ ⫺5040

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Ei 5 gM⫹ge⫺ ⫹ log T ⫺ 6.49 ⫹ log T 2 gM

where Ei is the ionization potential of the metal in eV (Table 4.2), T is the absolute temperature of the plasma (in kelvins), and the g terms are the statistical weights of the ionized atom, the electron, and the neutral atom. For the alkali metals the final term is zero; for the alkaline earth metals, it is 0.6. To suppress the ionization of a metal, another easily ionized metal (denoted a deionizer or radiation buffer) is added to the sample. To ensure that ionization is suppressed for the test element, the product (Ki)MpM of the deionizer must exceed the similar product for the test element one hundred-fold (for 1 percent residual ionization of the test element).

7.5

INFRARED SPECTROSCOPY

TABLE 7.20 Absorption Frequencies of Single Bonds to Hydrogen Abbreviations Used in the Table m, moderately strong var, of variable strength m– s, moderate to strong w, weak s, strong w– m, weak to moderately strong Group

Band, cm⫺1

Remarks

Saturated C 9 H H

2975– 2950 2885– 2865

(s) (w)

1450– 1260

(m)

9C9H H

ca 2930 (s) 2870– 2840 (w)

H 9C9

acyclic

H

1480– 1440 (m) ca 720 (w)

Two or three bands usually; asymmetrical and symmetrical CH stretching, respectively. In presence of double bond adjacent to CH 3 group symmetrical band splits into two. Sensitive to adjacent negative substituents Frequency increased in strained systems. Symmetrical band splits into two bands when double bond adjacent. Scissoring mode Rocking mode

Alkane residues attached to carbon Cyclopropane

Cyclobutanes Cyclopentanes

ca 3050 (w) 540– 500 470– 460 (s)

CH stretching

580– 490 595– 490

Alkyl derivatives: 550– 530 cm⫺1 Alkyl derivatives: 585– 530 cm⫺1

(s) (s)

Aliphatic cyclopropanes

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TABLE 7.20 Absorption Frequencies of Single Bonds to Hydrogen (Continued) Band, cm⫺1

Group

Remarks

Alkane residues attached to carbon (continued) C(CH3)2

ca 1380 (m) 1175– 1165 (m) 1150– 1130 (m)

A roughly symmetrical doublet If no H on central carbon, then one band at ca 1190 cm⫺1

9 C(CH 3 )3

1395– 1385 1365 (s)

Split into two bands

Aryl-CH 3 Aryl-C2 H 5 Aryl-C3 H 7 (or C4H 9)

390– 260 565– 540 585– 565

(m) (m– s) (m)

9 (CH 2 )n 9 n⫽1 n⫽2 n⫽3 nⱖ4

785– 770 745– 735 735– 725 725– 720

(w– m) (w– m) (w– m) (w– m)

(m)

Two bands

Rocking vibrations

Alkane residues attached to miscellaneous atoms Epoxide C 9 H

ca ca

NH C

3050 3050

(m– s) (m– s)

CH2

9 CH 2 9 halogen

ca 3050 (m– s) 1435– 1385 (m) 1300– 1240 (s)

9 CHO

2900– 2800 (w) 2775– 2700 (w) 1420– 1370 (m)

9 CO 9 CH 3

3100– 2900 1450– 1400 1360– 1355

9 O 9 CH 3 ethers

2835– 2810 (s) 1470– 1430 (m– s) ca 1030 (w– m)

(w) (s) (s)

9 O 9 C(CH 3 )3

1200– 1155

(s)

9 O 9 CH 2 9 O 9

2790– 2770

(m)

9 O 9 CH 2 9

1475– 1460 (m– s) 1470– 1435 (m– s)

esters

Halogens except fluorine

Two bands

Acyclic esters. Frequency increased ca 30 cm⫺1 for cyclic and small ring systems.

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TABLE 7.20 Absorption Frequencies of Single Bonds to Hydrogen (Continued) Band, cm⫺1

Group

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Remarks

Alkane residues attached to miscellaneous atoms (continued) 9 O 9 CO 9 CH 3

1450– 1400 1385– 1365 1360– 1355

(s) (s) (s)

9 CH2 9 C " C

1445– 1430

(m)

9 CH 2 9 SO2 9

ca

P 9 CH 3 Se 9 CH 3 B 9 CH 3

1320– 1280 (s) ca 1280 (m) 1460– 1405 (m) 1320– 1280 (m) 1265– 1250 (m– s) 1200– 1180 (m) 1170– 1155 (m) 1265– 1240 (m) 1240– 1230 (m) 1215– 1195 (m) 1165– 1145 (m) 1430– 1415 (m)

Si 9 CH 3 Sn 9 CH 3 Pb 9 CH 3 As 9 CH 3 Ge 9 CH 3 Sb 9 CH 3 Bi 9 CH 3 9 CH 2 9 (Cd, Hg, Zn, Sn) N 9 CH3 and N 9 CH 2 9 N 9 CH 2 9 CH 2 9 N N 9 CH 3 Amine · HCl Amino acid · HCl Amides N 9 CH 2 9 amides

1250

Acetate esters The high intensity of these bands often dominates this region of the spectrum.

(m)

2820– 2780 (s) 1440– 1390 (m) 1480– 1450 (s)

Ethylenediamine complexes Ethylenediamine complexes

1475– 1395 (m) 1490– 1480 (m) 1420– 1405 (s) ca 1440 (m)

S 9 CH 3

2990– 2955 (m– s) 2900– 2865 (m– s) 1440– 1415 (m) 1325– 1290 (m) 1030– 960 (m) 710– 685 (w– m)

S 9 CH 2 9

2950– 2930 2880– 2845 1440– 1415 1270– 1220

9 C # CH

ca 3300 700– 600

(m) (m) (m) (s) (s)

Sharp Bending

H C"C

3040– 3010

(m)

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TABLE 7.20 Absorption Frequencies of Single Bonds to Hydrogen (Continued) Band, cm⫺1

Group

Remarks

Alkane residues attached to miscellaneous atoms (continued) 3095– 3075 2985– 2970

H C"C

(m) (m)

H R

H C"C

H

H

995– 980 (s) 940– 900 (s) ca 635 (s) 485– 445 (m– s) 895– 885 560– 530 470– 435

(s) (s) (m)

980– 955 455– 370

(s) (m– s)

730– 655 670– 455

(m) (s)

850– 790 570– 515 525– 470

(m) (s) (s)

9 O 9 CH " CH 2

965– 960 945– 940 820– 810

(s) (m) (s)

9 S 9 CH " CH 2

ca ca

(s) (s)

9 CO 9 CH " CH 2

995– 980 (s) 965– 955 (m) 950– 935 (s) 870– 850 (s) ca 930 (s) 880– 865 940– 920 (s) ca 990 (s)

R

H C"C

R

H

R

H C"C

H

R

H

H C"C

R

R

R

H C"C

R

CH stretching sometimes obscured by much stronger bands of saturated CH groups

R

9 CO 9 OCH " CH 2 9 CO 9 C " CH 2 9 CO 9 OC " CH 2 9 O 9 CH " CH 9 trans 9 CO 9 CH " CH 9 trans

965 860

Hydroxyl group O 9 H compounds Primary aliphatic alcohols

3640– 3630

(s)

1350– 1260 1085– 1030

(s) (s)

Only in very dilute solutions in nonpolar solvents OH bending Also broad band at 700– 600 cm⫺1

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TABLE 7.20 Absorption Frequencies of Single Bonds to Hydrogen (Continued) Band, cm⫺1

Group

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Remarks

Hydroxyl group O 9 H compounds (continued) Secondary aliphatic alcohols

Tertiary aliphatic alcohols

Aryl 9 OH

3625– 3620

(s)

1350– 1260 1125– 1085

(s) (s)

3620– 3610

(s)

1410– 1310 1205– 1125

(s) (s)

ca

3610

(s)

1410– 1310 1260– 1180 1085– 1030

(s) (s) (s)

See comments under primary aliphatic alcohols Also for ␣-unsaturated and cyclic tertiary aliphatic alcohols See comments under primary aliphatic alcohols

See comments under primary aliphatic alcohols Also for unsaturated secondary aliphatic alcohols

Carboxylic acids

3300– 2500 (w– m) 995– 915 (s)

Broad Broad diffuse band

Enol form of ␤-diketones

2700– 2500

(var)

Broad

Free oximes

3600– 3570

(w– m)

Shoulder

Free hydroperoxides

3560– 3530

(m)

Peroxy acids

ca

Phosphorus acids

2700– 2560

Water in solution Intermolecular H bond Dimeric

Polymeric Intramolecular H bond Polyvalent alcohols Chelation

Water of crystallation (solid state spectra)

3280

(m) (m)

3710

Broad When solution is damp

3600– 3500

Rather sharp. Absorptions arising from H bond with polar solvents also appear in this region. Broad

3400– 3200

(s)

3600– 3500 3200– 2500

(s)

Sharper than dimeric band above Broad and occasionally weak; the lower the frequency, the stronger the intramolecular bond

3600– 3100

(w)

Usually a weak band at 1640– 1615 cm⫺1 also. Water in trace amounts in KBr disks shows a broad band at 3450 cm⫺1.

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TABLE 7.20 Absorption Frequencies of Single Bonds to Hydrogen (Continued) Band, cm⫺1

Group

Remarks

Amine, imine, ammonium, and amide N 9 H Primary amines Aliphatic

Aromatic Amino acids

Amino salts

Secondary amines

Salts

Tertiary amines R 1 R 2 R 3 NH⫹

3550– 3300 1650– 1560 1090– 1020 850– 810 495– 445 ca 290 1350– 1260 445– 345 3100– 3030

(m) (m) (w– m) (w– m) (m– s) (s) (s) (m)

2800– 2400 (m) 1625– 1560 (m) 1550– 1550 (m) 3550– 3100 (m) ca 3380 ca 3280 3550– 3400

(w)

1580– 1490 1190– 1170 1145– 1130 455– 405 ca 2500 ca 2400 1620– 1560

(w) (m) (m) (w– m)

Two bands in this range With ␣-carbon branching at 795 cm⫺1 and strong Broad Broad Also for secondary aryl amines Values for solid states; broad bands also (but not always) near 2500 and 200 cm⫺1 Number of sharp bands; dilute solution

Values for solid state Dilute solutions

Only one band, whereas primary amines show two bands Often too weak to be noticed

Sharp; broad values for solid state Sharp; broad values for solid state (m– s)

2700– 2250

Group of relatively sharp bands; broad bands in solid state

Ammonium ion

3300– 3030 (s) 1430– 1390 (s)

Group of bands

Imines " N " H

3350– 3310 (w) 3490 (s) 3490 (s)

Aliphatic Aryl Pyrroles, indoles; band sharp

Imine salts

2700– 2330 (m– s) 2200– 1800 (m)

Dilute solutions One or more bands; useful to distinguish from protonated tertiary amines

Primary amide 9 CONH 2

ca ca

Lowered ca 150 cm⫺1 in the solid state and on H bonding; often several bands 3200– 3050 cm⫺1

Secondary amide 9 CONH 9

3460– 3400

(m)

3100– 3070

(w)

3500 3400

(m) (m)

Two bands; lowered on H bonding and in solid state. Only one band with lactams Extra band with bonded and solid-state samples

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TABLE 7.20 Absorption Frequencies of Single Bonds to Hydrogen (Continued) Band, cm⫺1

Group

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Remarks

Miscellaneous R 9 H 9S9H

2600– 2550

(w)

P9H O P OH R9D

2440– 2350

(m)

Weaker than OH and less affected by H bonding Sharp

2700– 2560

(m)

Associated OH

100/137 times the corresponding RH frequency

Useful when assigning RH bands; deuteration leads to a known shift to lower frequency

TABLE 7.21 Absorption Frequencies of Triple Bonds Abbreviations Used in the Table m, moderately strong var, of variable strength m– s, moderate to strong w– m, weak to moderately strong s, strong Group Alkynes Terminal

Nonterminal

R1 9 C # C 9 R2

Aryl 9 C # C 9

9 C # C 9 halogen (Cl, Br, I)

Band, cm⫺1

3300 (s) 2140– 2100 (w– m)* 1375– 1225 (w– m) 695– 575 (m– s) ca 630 (s) 2260– 2150 (var)*

540– 465 (m)

Remarks

CH stretching C # C stretching Two bands if molecule has axial symmetry Alkyl monosubstituted Symmetrical or nearly symmetrical substitution makes the C # C stretching frequency inactive. When more than one C # C linkage is present, and sometimes when there is only one, there are frequently more absorption bands in this region than there are triple bonds to account for them. The longer the chain, the lower the frequency

ca 550 (m) ca 350 (var) 185– 160 (var)

* Conjugation with olefinic or acetylenic groups lowers the frequency and raises the intensity. Conjugation with carbonyl groups usually has little effect on the position of absorption.

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TABLE 7.21 Absorption Frequencies of Triple Bonds (Continued) Band, cm⫺1

Group Nitriles

9C#N

2260– 2200 (var)

Aliphatic

Remarks Stronger and toward the lower end of the range when conjugated; occasionally very weak or absent

580– 555 (m– s) 560– 525 (m– s) 390– 350 (s) 580– 540 (s) 430– 380 (m)

Aromatic ⫹

⫺

Isonitriles R 9 N # C or R 9 N " C:

Cyanamides N9C#N L Thiocyanates R9S9C#N

2175– 2150 (s) 2150– 2115 (s) 1595 ⫹

⫺

N9C"N

2225– 2210 (s)

2175– 2140 (s) 404– 400 (s) ca 600 (m– s)

Nitrile N-oxides 9 C # N:O

Diazonium salts ⫹ R9N#N Selenocyanates R 9 Se 9 C # N

Very sensitive to changes in substituents Not found for nitriles

2305– 2285 (s) 1395– 1365 (s)

Aryl thiocyanates at the upper end of the range, alkyl at the lower end Aliphatic derivatives

Aryl derivatives

2300– 2230 (m– s)

ca 2160 (m– s) 545– 520 ca 390 ca 350

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TABLE 7.22 Absorption Frequencies of Cumulated Double Bonds Abbreviations Used in the Table m– s, moderate to strong s, strong Group Carbon dioxide O"C"O

Isocyanates 9N"C"O Isoselenocyanates 9 N " C " Se

Azides ⫹ ⫺ 9 N3 or 9 N " N " N

9N"C"N9

Isothiocyanates 9N"C"S

Band, cm⫺1

Remarks

2349 (s)

Appears in many spectra as a result of inequalities in path length

2275– 2250 (vs)

Position unaffected by conjugation

2200– 2000 (s) 675– 605

Broad; usually two bands

2140– 2030 (s) 1340– 1180 (w)

Split into unsymmetrical doublet by conjugation with aryl groups: 2145– 2125 (vs) and 2115– 2105 (vs)

2140– 1990 (vs) 649– 600 (m– s) 565– 510 (m– s) 470– 440 (m– s)

Broad; usually a doublet

ca 2150 (s)

Ketenimines C"C"N9

2050– 2000 (s)

Allenes C"C"C

2000– 1915 (m– s)

Diazoalkanes ⫹ ⫺ R2C " N " N⫺ ⫹ 9 CH " N " N Diazoketones ⫹ ⫺ 9 CO 9 CH " N " N

Not observed for ionic azides

2155– 2130 (s)

Ketenes C"C"O

Thionylamines 9N"S"O

vs, very strong w, weak

Two bands when terminal allene or when bonded to electron-attracting groups

1300– 1230 (s) 1180– 1110 (s)

2030– 2000 (s) 2050– 2035 (s)

2100– 2080 2075– 2050

Monosubstituted Disubstituted

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TABLE 7.23 Absorption Frequencies of Carbonyl Bands All bands quoted are strong. Groups Acid anhydrides 9 CO 9 O 9 CO 9 Saturated

Aryl and ␣,␤-unsaturated Saturated five-ring All classes Acid chlorides 9 COCl Saturated Aryl and ␣,␤-unsaturated Acid peroxide CO 9 O 9 O 9 CO 9 Saturated Aryl and ␣,␤-unsaturated Esters and lactones 9 CO 9 O 9 Saturated Aryl and ␣,␤-unsaturated Aryl and vinyl esters C " C 9 O 9 CO 9 alkyl Esters with electronegative ␣ substituents; e.g., CCl 9 CO 9 O 9 ␣-Keto esters Six-ring and larger lactones

Five-ring lactone ␣,␤-Unsaturated five-ring lactone

␤,␥-Unsaturated five-ring lactone, vinyl ester type Four-ring lactone ␤-Keto ester in H bonding enol form

All classes

Band, cm⫺1

1850– 1800 1790– 1740

1830– 1780 1790– 1710 1870– 1820 1800– 1750 1300– 1050 1815– 1790

Remarks

Two bands usually separated by about 60 cm⫺1. The higher-frequency band is more intense in acyclic anhydrides, and the lower-frequency band is more intense in cyclic anhydrides.

One or two strong bands due to CO stretching Acid fluorides higher, bromides and iodides lower

1790– 1750

1820– 1810 1800– 1780 1805– 1780 1785– 1755

1750– 1735 1730– 1715 1800– 1750

The C " C stretching band also shifts to higher frequency.

1770– 1745 1755– 1740 Similar values to the corresponding open-chain esters 1780– 1760 1770– 1740

When ␣-CH is present, there are two bands, the relative intensity depending on the solvent.

ca 1800 ca 1820 ca 1650

1300– 1050

Keto from normal; chelate-type H bond causes shift to lower frequency than the normal ester. The C " C band is strong and is usually near 1630 cm⫺1. Usually two strong bands due to CO stretching

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TABLE 7.23 Absorption Frequencies of Carbonyl Bands (Continued) Groups Aldehydes 9 CHO (See also Table 7.49 for C 9 H.) All values given below are lowered in liquid-film or solid-state spectra by about 10– 20 cm⫺1. Vapor-phase spectra have values raised about 20 cm⫺1. Saturated Aryl

␣,␤-Unsaturated ␣,␤,␥,␦-Unsaturated ␤-Ketoaldehyde in enol form Ketones C O All values given below are lowered in liquid-film or solid-state spectra by about 10– 20 cm⫺1. Vapor-phase spectra have values raised about 20 cm⫺1. Saturated Aryl ␣,␤-Unsaturated ␣,␤,␣⬘,␤⬘-Unsaturated and diaryl Cyclopropyl Six-ring ketones and larger

Band, cm⫺1

1740– 1720 1715– 1695

Remarks

o-Hydroxy or amino groups shift this value to 1655– 1625 cm⫺1 because of intramolecular H bonding.

1705– 1680 1680– 1660 1670– 1645

Lowering caused by chelate-type H bonding

1725– 1705 1700– 1680 1685– 1665

Five-ring ketones

1670– 1660 1705– 1685 Similar values to the corresponding open-chain ketones 1750– 1740

Four-ring ketones ␣-Halo ketones

ca 1780 1745– 1725

␣,␣⬘-Dihalo ketones 1,2-Diketones, syn-transopen chains

1765– 1745

syn-cis-1,2-Diketones, sixring syn-cis-1,2-Diketones, five ring

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1730– 1710

␣,␤ Unsaturation, ␣,␤,␣⬘,␤⬘ unsaturation, etc., have a similar effect on these values as on those of open-chain ketones. Affected by conformation; highest values are obtained when both halogens are in the same plane as the C " O.

Antisymmetrical stretching frequency of both C " O’s. The symmetrical stretching is inactive in the infrared but active in the Raman.

1760 and 1730 1775 and 1760

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TABLE 7.23 Absorption Frequencies of Carbonyl Bands (Continued) Groups Ketones C O (continued) o-Amino-aryl or o-hydroxyaryl ketones

Band, cm⫺1

1655– 1635

Quinones

1690– 1660

Extended quinones Tropone

1655– 1635 1650

Carboxylic acids 9 CO2H All types Saturated

␣,␤-Unsaturated Aryl ␣-HaloCarboxylate ions 9 COⴚ2 Most types Amides CO N (See also Table 7.49 for NH stretching and bending.) Primary 9 CONH2 In solution Solid state In solution Solid state

3000– 2500 1725– 1700

1610– 1550 1420– 1300

ca 1690 ca 1650 ca 1600 ca 1640

1700– 1670 1680– 1630 1550– 1510 1570– 1515

Tertiary

1670– 1630

C " C 9 CO 9 N

Low because of intramolecular H bonding. Other substituents and steric hindrance affect the position of the band. C " C band is strong and is usually near 1600 cm⫺1. Near 1600 cm⫺1 when lowered by H bonding as in tropolones OH stretching; a characteristic group of small bands due to combination bands The monomer is near 1760 cm⫺1, but is rarely observed. Occasionally both bands, the free monomer, and the H-bonded dimer can be seen in solution spectra. Ether solvents give one band near 1730 cm⫺1.

1715– 1690 1700– 1680 1740– 1720

Secondary 9 CONH 9 In solution Solid state In solution Solid state

Lactams Six-ring and larger rings Five-ring Four-ring R 9 CO 9 N 9 C " C

Remarks

ca 1670 ca 1700 ca 1745

Antisymmetrical and symmetrical stretching, respectively

Amide I; C " O stretching Amide II: mostly NH bending Amide I is generally more intense than amide II. (In the solid state, amides I and II may overlap.) Amide I Amide II; found in open-chain amides only Amide I is generally more intense than amide II. Since H bonding is absent, solid and solution spectra are much the same. Shifted to higher frequency when the N atom is in a bridged system Shifted ⫹15 cm⫺1 by the additional double bond Shifted by up to ⫹15 cm⫺1 by the additional double bond. This is an unusual effect by ␣,␤ unsaturation. It is said to be due to the inductive effect of the C " C on the wellconjugated CO 9 N system, the usual conjugation effect being less important in such a system.

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TABLE 7.23 Absorption Frequencies of Carbonyl Bands (Continued) Groups Imides 9 CO 9 N 9 CO 9 Cyclic six-ring Cyclic five-ring Ureas N 9 CO 9 N RNHCONHR Six-ring Five-ring Urethanes R 9 O 9 CO 9 N Thioesters and Acids RCO 9 S 9 R⬘ RCOSH RCOS 9 alkyl RCOS 9 aryl

7.5.1

Band, cm⫺1

ca 1710 and ca 1700 ca 1770 and ca 1700 ca 1660 ca 1640 ca 1720 1740– 1690

ca 1720

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Remarks

Shift of ⫹15 cm⫺1 with ␣,␤ unsaturation

Also shows amide II band when nonsubstituted on N

␣,␤-Unsaturated or aryl acid or ester shifted about ⫺25 cm⫺1

ca 1690 ca 1710

Intensities of Carbonyl Bands

Acids generally absorb more strongly than esters, and esters more strongly than ketones or aldehydes. Amide absorption is usually similar in intensity to that of ketones but is subject to much greater variations.

7.5.2

Position of Carbonyl Absorption

The general trends of structural variation on the position of C"O stretching frequencies may be summarized as follows: 1. The more electronegative the group X in the system R9CO9X 9 , the higher is the frequency. 2. ␣, ␤ Unsaturation causes a lowering of frequency of 15 to 40 cm⫺1, except in amides, where little shift is observed and that usually to higher frequency. 3. Further conjugation has relatively little effect. 4. Ring strain in cyclic compounds causes a relatively large shift to higher frequency. This phenomenon provides a remarkably reliable test of ring size, distinguishing clearly between four-, five-, and larger-membered-ring ketones, lactones, and lactams. Six-ring and larger ketones, lactones, and lactams show the normal frequency found for the open-chain compounds. 5. Hydrogen bonding to a carbonyl group causes a shift to lower frequency of 40 to 60 cm⫺1. Acids, amides, enolized ␤-keto carbonyl systems, and o-hydroxyphenol and o-aminophenyl carbonyl compounds show this effect. All carbonyl compounds tend to give slightly lower values for the carbonyl stretching frequency in the solid state compared with the value for dilute solutions. 6. Where more than one of the structural influences on a particular carbonyl group is operating, the net effect is usually close to additive.

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TABLE 7.24 Absorption Frequencies of Other Double Bonds Abbreviations Used in the Table m, moderately strong vs, very strong m– s, moderate to strong w, weak var, of variable strength Band, cm⫺1

Group

Alkenes

Remarks

C"C

Nonconjugated

1680– 1620 (w– m)

May be very weak if symmetrically substituted

Conjugated with aromatic ring

1640– 1610 (m)

More intense than with unconjugated double bonds

Internal (ring)

3060– 2995 (m)

Highest frequencies for smallest ring

Carbons: n ⫽ 3 n⫽4 n⫽5

ca 1665 (w– m) ca 1565 (w– m) ca 1610 (w– m) 1370– 1340 (s) 1650– 1645 (w– m)

nⱖ6 Exocyclic

C" C(CH2)n n ⫽ 2 n⫽3 nⱖ4

Fulvene

Characteristic

1780– 1730 (m) ca 1680 (m) 1655– 1650 (m) 1645– 1630 (m) 1370– 1340 (s) 790– 765 (s)

Dienes, trienes, etc.

1650 (s) and 1600 (s)

␣,␤-Unsaturated carbonyl compounds

1640– 1590 (m)

Enol esters, enol ethers, and enamines

1700– 1650 (s) Imines, oximes, and amidines

Imines and oximes Aliphatic ␣,␤-Unsaturated and aromatic Conjugated cyclic systems Imino ethers 9 O 9 C " N 9

Lower-frequency band usually more intense and may hide or overlap the higher-frequency band Usually much weaker than the C " O band

C"N9

1690– 1640 (w) 1650– 1620 (m) 1660– 1480 (var) 960– 930 (s)

NO stretching of oximes

1690– 1640 (var)

Usually a strong doublet

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TABLE 7.24 Absorption Frequencies of Other Double Bonds (Continued) Band, cm⫺1

Group

Imines, oximes, and amidines Imino thioethers 9 S 9 C " N " ⫹

Imine oxides Amidines

⫺

C"N9O N9C"N9

Benzamidines Guanidine

Aryl 9 C " N 9 N N9C"N9

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Remarks

C " N 9 (continued)

1640– 1605 (var) 1620– 1550 (s) 1685– 1580 (var) 1630– 1590 1725– 1625 (s)

N Azines

C"N9N"C

Hydrazoketones 9 CO 9 C " N 9 N

1670– 1600

1600– 1530 (vs) Azo compounds 9 N " N 9

Azo 9 N " N 9 Aliphatic Aromatic cis trans Azoxy

ca 1575 (var)

Very weak or inactive

ca 1510 (w) 1440– 1410 (w)

⫹

9N"N9 O⫺

Aliphatic

1590– 1495 (m– s) 1345– 1285 (m– s) 1480– 1450 (m– s) 1340– 1315 (m– s)

Aromatic

⫹

⫺

Azothio 9 N " N 9 S 9

1465– 1445 (w) 1070– 1055 (w) Nitro compounds N " O

Nitro C 9 NO2 Aliphatic

ca 1560 (s) 1385– 1350 (s)

The two bands are due to asymmetrical and symmetrical stretching of the N " O bond. Electronwithdrawing substituents adjacent to nitro group increase the frequency of the asymmetrical band and decrease that of the symmetrical frequency.

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TABLE 7.24 Absorption Frequencies of Other Double Bonds (Continued) Group

Band, cm⫺1

Remarks

Nitro compounds N " O (continued) Nitro C 9 NO2 (continued) Aromatic

1570– 1485 (s) 1380– 1320 (s)

865– 835 (s)

␣,␤-Unsaturated Nitroalkenes Nitrates 9 O 9 NO2

N 9 NO2

Nitramines

Nitrates 9 O 9 N " O

Thionitrites 9 S 9 N " O C9N"O

Nitroso ⫹

See above remark; also bulky orthosubstituents shift band to higher frequencies. Strong H bonding shifts frequency to lower end of range. Strong and sometimes at ca 750 cm⫺1

580– 520 (var) 1530– 1510 (s) 1360– 1335 (s) 1650– 1625 (vs) 1285– 1275 (vs) 870– 855 (vs) 760– 755 (w– m) 710– 695 (w– m) 1630– 1550 (s) 1300– 1250 (s) 1680– 1610 (vs) 815– 750 (s) 850– 810 (s) 690– 615 (s)

Two bands Trans form Cis form

730– 685 (m– s) 1600– 1500 (s)

⫺

N9N"O Aliphatic Aromatic

Nitrogen oxides Pyridine Pyrazine

1530– 1495 (m– s) 1480– 1450 (m– s) 1335– 1315 (m– s) N:O 1320– 1230 (m– s) 1190– 1150 (m– s) 1380– 1280 (m– s) 1040– 990 (m– s) ca 850 (m)

Affected by ring substituents

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TABLE 7.25 Absorption Frequencies of Aromatic Bands Abbreviations Used in the Table m, moderately strong m– s, moderate to strong s, strong Group Aromatic rings

Five adjacent H

Band, cm⫺1

Remarks

ca 1600 (m) ca 1580 (m) ca 1470 (m) ca 1510 (m)

Stronger when ring is further conjugated When substituent on ring is electron acceptor When substituent on ring is electron donor

900– 860 (w– m) 770– 730 (s) 720– 680 (s) 625– 605 (w– m) ca 550 (w– m)

1,2-Substitution

770– 735 (s) 555– 495 (w– m) 470– 415 (m– s)

1,3-Substitution

810– 750 (s) 560– 505 (m) 460– 415 (m– s)

1,4-Substitution

var, of variable strength w– m, weak to moderately strong

860– 800 (s) 650– 615 (w– m) 520– 440 (m– s)

1,2,3-Trisubstitution

800– 760 (s) 720– 685 (s) 570– 535 (s) ca 485

1,2,4-Trisubstitution

900– 885 (m) 780– 760 (s) 475– 425 (m– s)

1,3,5-Trisubstitution

950– 925 (var) 865– 810 (s) 730– 680 (m– s) 535– 495 (s) 470– 450 (w– m)

Pentasubstitution

900– 860 (m– s) 580– 535 (s)

Hexasubstitution

415– 385 (m– s)

Substituents: C " C, C # C, C # N

490– 460 cm⫺1 when substituents are electron-accepting groups

520– 490 cm⫺1 when substituents are electron-donating groups

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TABLE 7.26 Absorption Frequencies of Miscellaneous Bands Abbreviations Used in the Table m, moderately strong vs, very strong m– s, moderate to strong w, weak s, strong w– m, weak to moderately strong var, of variable strength Group

Band, cm⫺1

Remarks

Ethers Saturated aliphatic C9O9C

1150– 1060 (vs)

1140– 900 (s)

Two peaks may be observed for branched chain, usually 1140– 1110 cm⫺1. Usually 930– 900 cm⫺1; may be absent for symmetric ethers

Alkyl– aryl "C9O9C

Vinyl Diaryl "C9O9C"

Cyclic Epoxides C C O

Ketals and acetals

Phthalanes Aromatic methylenedioxy

1270– 1230 (vs) 1120– 1020 (s)

"CO stretching CO stretching

1225– 1200 (s)

Usually about 1205 cm⫺1

1200– 1120 (s) 1100– 1050 (s) 1270– 1030 (s)

1260– 1240 (m– s) 880– 805 (m) 950– 860 (var) 865– 785 (m) 770– 750 (m)

Monosubstituted Trans form Cis form Trisubstituted

1190– 1140 (s) 1195– 1125 (s) 1100– 1000 (s) 1060– 1035 (s)

Strongest band Sometimes obscured

915– 895 (s) 1265– 1235 (s) Peroxides

9O9O9

900– 830 (w) 1150– 1030 (m– s) ca 1000 (m)

Alkyl Aryl

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TABLE 7.26 Absorption Frequencies of Miscellaneous Bands (Continued) Group

Band, cm⫺1

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Remarks

Sulfur compounds Thiols 9S9H 9 CO 9 SH 9 CS 9 SH

2600– 2450 (w) 840– 830 (m) ca 860 (s)

Thiocarbonyl C"S

1200– 1050 (s)

N9C"S

Broad

Behaves generally in manner similar to carbonyl band

1570– 1395 1420– 1260 1140– 940 ca 580 (s)

9S9C"S

Sulfoxides S" O

1075– 1040 (vs)

Halogen or oxygen atom bonded to sulfur increases the frequency.

730– 690 (var) 395– 360 (var) Sulfones SO2

1360– 1290 (vs)

Halogen or oxygen atom bonded to sulfur increases the frequency.

1170– 1120 (vs) 610– 545 (m– s) 525– 495 (m– s) Sulfonamides 9SO29 N

Sulfonates 9 SO2 9 O 9

Thiosulfonates 9 SO2 9 S 9 Sulfates 9 O 9 SO2 9 O 9 Primary alkyl salts Secondary alkyl salts

1380– 1330 (vs) 1170– 1140 (vs) 950– 860 (m) 715– 700 (w– m)

1420– 1330 (s) 1200– 1145 (s)

May appear as doublet

ca 1340 (vs) 1415– 1380 (s) 1200– 1185 (s) 1315– 1220 (s) 1140– 1075 (m) 1270– 1210 (vs) 1075– 1050 (s)

Electronegative substituents increase frequencies. Strongly influenced by metal ion Doublet; both bands strongly influenced by metal ion

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TABLE 7.26 Absorption Frequencies of Miscellaneous Bands (Continued) Group

Band, cm⫺1

Remarks

Sulfur compounds (continued) Stretching frequencies of C 9 S and S 9 S bonds 9 S 9 CH 3 9 S 9 CH 2 9 9S 9 CH 9S 9 C 9 S 9 aryl R9S9S9R Aryl 9 S 9 S 9 aryl Polysulfides CH 2 9 S 9 CH 2 9 (R 9 S)2C " O 9 CO 9 S 9 9 CS 9 S S9 "C S9

710– 685 (w– m) 660– 630 (w– m) 630– 600 (w– m) 600– 570 (w– m) 1110– 1070 (m) 710– 685 (w– m) 705– 570 (w) 520– 500 (w) 500– 430 (w– m) 500– 470 (w– m) 695– 655 (w– m) 880– 825 (s) 570– 560 (var) 1035– 935 (s) ca 580 (s) 1050– 900 (m– s) 980– 850 (m– s) 900– 800 (m– s)

CSC stretching

Monoionic Ionic 1,1-dithiolates

Phosphorus compounds P9H

2455– 2265 (m)

Sharp. Phosphines lie in the region 2285– 2265 cm⫺1.

1150– 965 (w– m) 9 PH 2

P 9 alkyl

1100– 1085 (m) 1065– 1040 (w– m) 940– 910 (m) 795– 650 (m– s)

P 9 aryl

1130– 1090 (s) 750– 680 (s)

P 9 O 9 alkyl

1050– 970 (s)

P 9 O 9 aryl

1240– 1190 (s)

P9O9P P"O O P OH

970– 910

Broad

Broad

1350– 1150 (s)

May appear as doublet

2725– 2520 (w– m) 2350– 2080 (w– m) 1740– 1600 (w– m) 1335 (s) 1090– 910 (s) 540– 450 (w– m)

H-bonded; broad Broad; may be doublet for aryl acids P " O stretching

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TABLE 7.26 Absorption Frequencies of Miscellaneous Bands (Continued) Group

Band, cm⫺1

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Remarks

Phosphorus compounds (continued) P"S S P OH

865– 655 (m– s) 595– 530 (var) 3100– 3000 (w) 2360– 2200 (w) 935– 910 (s) 810– 750 (m– s) 655585 (var)

PO stretching P " S stretching P " S stretching

Silicon compounds Si 9 H

Si 9 C

2250– 2100 (s) 985– 800 860– 760

Accompanied by CH 2 rocking

Si 9 C

1280– 1250 (s)

Si 9 C2 H 5

1250– 1220 (m) 1020– 1000 (m) 970– 945 (m)

Si 9 Aryl

1125– 1090 (vs)

Si 9 OH Si 9 O 9 Si

SiH 3 has two bands.

870– 820

Sharp

Splits into two bands when two aryl groups are attached to one silicon atom, but has only one band when three aryl groups attached OH deformation band

1100– 1000

Si 9 N 9 Si

940– 870 (s)

Si 9 Cl

550– 470 (s) 250– 150

SiCl2

595– 535 (s) 540– 460 (m)

9 SiCl 3

625– 570 (s) 535– 450 (m) Boron compounds

Boranes BH or 9 BH2

2640– 2450 2640– 2570 2535– 2485 2380– 2315 2285– 2265 2140– 2080 2580– 2450

(m– s) (m– s) (m– s) (s) (s) (w– m) (m)

Free H in BH Free H in BH 2 plus second band In complexes; second band for BH 2 Bridged H Borazoles and borazines

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TABLE 7.26 Absorption Frequencies of Miscellaneous Bands (Continued) Group

Band, cm⫺1

Remarks

Boron compounds (continued) BH⫺4

2310– 2195 (s)

Two bands

B9N

1550– 1330 750– 635

Borazines and borazoles

B9O

1390– 1310 (s) 1280– 1200

BO stretching Metal orthoborates

B 9 Cl B 9 Br

1090– 890 (s)

Plus other bands at lower frequencies for BX2 and BX3

B9F

1500– 840 (var)

Isotope splitting present

XBF2

1500– 1410 (s) 1300– 1200 (s)

X 2 BF

1360– 1300 (s)

BF3 complexes

1260– 1125 (s)

Band splitting may be added to isotopic splittings.

1030– 800 (s) BF⫺4

ca 1030 (vs) Halogen compounds

C9F Aliphatic, mono-F Aliphatic, di-F Aliphatic, poly-F Aromatic

9 CF3 Aliphatic

Aromatic

C 9 Cl Primary alkanes

1110– 1000 (vs) 780– 680 (s) 1250– 1050 (vs) 1360– 1090 (vs) 1270– 1100 (m) 680– 520 (m– s) 420– 375 (var) 340– 240 (s)

Two bands Number of bands

1350– 1120 (vs) 780– 680 (s) 680– 590 (s) 600– 540 (s) 555– 505 (s) 1330– 1310 (m– s) 600– 580 (s)

730– 720 (s) 685– 680 (s) 660– 650 (s)

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TABLE 7.26 Absorption Frequencies of Miscellaneous Bands (Continued) Group

Band, cm⫺1

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Remarks

Halogen compounds (continued) C 9 Cl (continued) Secondary alkanes

Tertiary alkanes Poly-Cl Aryl: 1,21,31,4-

ca 760 (m) 675– 655 (m– s) 615– 605 (s) 635– 610 (m– s) 580– 560 (m– s) 800– 700 (vs) 1060– 1035 (m) 1080– 1075 (m) 1100– 1090 (m)

Chloroformates

ca 690 (s) 485– 470 (s)

Axial Cl Equatorial Cl

730– 580 (s) 780– 740 (s)

C 9 Br Primary alkanes

Secondary alkanes

Tertiary alkanes Axial Equatorial Aryl: 1,21,3-; 1,4Other bands

C9I Primary alkanes Secondary alkanes

Tertiary alkanes

Aromatic

Axial Equatorial

645– 635 (s) 565– 555 (s) 440– 430 (var) 620– 605 (s) 590– 575 (m– w) 540– 530 (s) 600– 595 (m– s) 525– 505 (s) 690– 550 (s) 750– 685 (s) 1045– 1025 (m) 1075– 1065 (m) 400– 260 (s) 325– 175 (m– s) 290– 225 (m– s)

600– 585 (s) 515– 500 (s) ca 575 (s) 550– 520 (s) 490– 480 (s) 580– 560 (s) 510– 485 (m) 485– 465 (s) 1060– 1055 (m– s) 310– 160 (s) 265– 185 ca 640 (s) ca 655 (s)

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TABLE 7.26 Absorption Frequencies of Miscellaneous Bands (Continued) Group

Band, cm⫺1

Remarks

Inorganic ions Ammonium

3300– 3030

Cyanate

2220– 2130 (s)

Cyanide

2200– 2000

Carbonate

1450– 1410

Hydrogen sulfate

1190– 1160 (s) 1180– 1000 (s) 880– 840 (m)

Nitrate

1410– 1350 (vs) 860– 800 (m)

Nitrite

1275– 1230 (s) 835– 800 (m)

Phosphate

1100– 1000

Sulfate

1130– 1080 (s)

Thiocyanate

Several bands, all strong

Shoulder

ca 2050 (s)

TABLE 7.27 Absorption Frequencies in the Near Infrared Values in parentheses are molar absorptivity. Class Acetylenes

Band, cm⫺1

Remarks

9800– 9430 6580– 6400 (1.0)

Overtone of # CH stretching

Alcohols (nonhydrogen-bonded)

7140– 7010 (2.0)

Overtone of OH stretching

Aldehydes Aliphatic

4640– 4520 (0.5)

Combination of C " O and CH stretchings

Aromatic

Formate

ca 8000 ca 4525 ca 4445 4775– 4630 (1.0)

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TABLE 7.27 Absorption Frequencies in the Near Infrared (Continued) Class Alkanes 9 CH 3

9 CH 2 9

CH Cyclopropane

Band, cm⫺1

9000– 8350 (0.02) 5850– 5660 (0.1) 4510– 4280 (0.3) 9170– 8475 (0.02) 5830– 6640 (0.1) 4420– 4070 (0.25) 8550– 8130 7000– 6800 5650– 5560 6160– 6060 4500– 4400

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Remarks

All bands very weak

Alkenes C"C

6850– 6370 (1.0)

H C " CH2 and 9 CH " CH2

H

7580– 7300 (0.02) 6140– 5980 (0.2) 4760– 4700 (1.2)

H C"C

9 O 9 CH " CH 2 9 CO 9 CH " CH 2

Amides Primary

Secondary

Amines, aliphatic Primary

Secondary

Amines, aromatic Primary

Secondary

4760– 4660 (0.15) 6250– 6040 7580– 7410 6190– 5990 4820– 4750

Trans isomers have no unique bands.

(0.3) (0.02) (0.3) (0.2– 0.5)

7400– 6540 (0.7) 5160– 5060 (3.0) 5040– 4990 (0.5) 4960– 4880 (0.5) 7330– 7140 (0.5) 5050– 4960 (0.4)

Two bands; overtone of NH stretch Second overtone of C " O stretch; second overtone of NH deformation; combination of C " O and NH Overtone of NH stretch Combination of NH stretch and NH bending

9710– 9350 6670– 6450 (0.5) 5075– 4900 (0.7)

Second overtone of NH stretch Two bands; overtone of NH stretch Two bands; combination of NH stretch and NH bending Second overtone of NH stretch Overtone of NH stretch

9800– 9350 6580– 6410 (0.5)

9950– 9520 7040– 6850 6760– 6580 5140– 5040 10 000– 9710 6800– 6580

(0.4) (0.2) (1.4) (1.5) (0.5)

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TABLE 7.27 Absorption Frequencies in the Near Infrared (Continued) Class Aryl-H

Band, cm⫺1 7660– 7330 (0.1) 6170– 5880 (0.1)

Carbonyl

5200– 5100

Carboxylic acids

7000– 6800

Epoxide (terminal)

6135– 5960 (0.2) 4665– 4520 (1.2)

Glycols Hydroperoxides Aliphatic Aromatic

6940– 6750 (2.0) 4960– 4880 (0.8) 7040– 6760 (1.0) 4950– 4850 (1.3) 9900– 9620 6540– 6370

Nitriles

5350– 5200 (0.1)

Oximes

7140– 7050

Phosphines

5350– 5260 (0.2)

Intramolecularly bonded Thiols

Overtone of CH stretch

Cyclopropane bands in same region

7140– 7040

Imides

Phenols Nonbonded

Remarks

Two bands

7140– 6800 (3.0) 5000– 4950 7000– 6700 5100– 4950 (0.05)

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TABLE 7.28 Infrared Transmitting Materials

Material NaCl, rock salt KBr, potassium bromide KCl, potassium chloride AgCl, silver chloride* AgBr, silver bromide* CaF2 , calcium fluoride (Irtran-3) BaF2 , barium fluoride MgO, magnesium oxide (Irtran-5) CsBr, cesium bromide CsI, cesium iodide TlBr-TlI, thallium bromide-iodide (KRS-5)* ZnS, zinc sulfide (Irtran-2) ZnSe, zinc selenide* (vacuum deposited) (Irtran-4) CdTe, cadmium telluride (Irtran-6) Al 2O3 , sapphire* SiO2 , fused quartz Ge, germanium* Si, silicon* Polyethylene

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Wavelength range, ␮m

Wavenumber range, cm⫺1

Refractive index at 2 ␮m

0.25– 17 0.25– 25 0.30– 20 0.40– 23 0.50– 35 0.15– 9 0.20– 11.5 0.39– 9.4 1– 37 1– 50 0.50– 35

40 000– 590 40 000– 400 33 000– 500 25 000– 435 20 000– 286 66 700– 1 110 50 000– 870 25 600– 1 060 10 000– 270 10 000– 200 20 000– 286

1.52 1.53 1.5 2.0 2.2 1.40 1.46 1.71 1.67 1.74 2.37

0.57– 14.7 1– 18

17 500– 680 10 000– 556

2.26 2.45

2– 28 0.20– 6.5 0.16– 3.7 0.50– 16.7 0.20– 6.2 16– 300

5 000– 360 50 000– 1538 62 500– 2 700 20 000– 600 50 000– 1 613 625– 33

2.67 1.76 4.0 3.5 1.54

* Useful for internal reflection work.

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TABLE 7.29 Infrared Transmission Characteristics of Selected Solvents Transmission below 80%, obtained with a 0.10-mm cell path, is shown as shaded area.

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TABLE 7.29 Infrared Transmission Characteristics of Selected Solvents (Continued)

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RAMAN SPECTROSCOPY

TABLE 7.30 Raman Frequencies of Single Bonds to Hydrogen and Carbon Abbreviations Used in the Table m, moderately strong vw, very weak m– s, moderate to strong w, weak m– vs, moderate to very strong w– m, weak to moderately strong s, strong w– vs, weak to very strong vs, very strong Group

Band, cm⫺1

Remarks

Saturated C 9 H and C 9 C 9 CH 3

9 CH 2 9

9 CH(CH 3 )2

9 C(CH 3 )3

Internal tertiary carbon atom

Internal quaternary carbon atom

2969– 2967 (s) 2884– 2883 (s) ca 1205 (s) 1150– 1135 1060– 1056 975– 835 (s) 280– 220 2949– 2912 (s) 2861– 2849 (s) 1473– 1443 (m– vs) 1305– 1295 (s) 1140– 1070 (m) 888– 837 (w) 425– 150 500– 490 1350– 1330 (m) 835– 750 (s)

1265– 1240 (m) 1220– 1200 (m) 760– 685 (vs)

In aryl compounds In unbranched alkyls In unbranched alkyls Terminal rocking of methyl group CH 2 9 CH 3 torsion

Intensity proportional to number of CH 2 groups Often two bands; see above

Substituent on aromatic ring

If attached to C " C bond, 870– 800 cm⫺1. If attached to aryl ring, 740 cm⫺1 Not seen in tert-butyl bromide Not seen in tert-butyl bromide If attached to C " C or aromatic ring, 760– 720 cm⫺1

855– 805 (w) 455– 410

710– 680 (vs) 490– 470

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TABLE 7.30 Raman Frequencies of Single Bonds to Hydrogen and Carbon (Continued) Band, cm⫺1

Group

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Remarks

Saturated C 9 H and C 9 C (continued) Two adjacent tertiary carbon atoms

Dialkyl substitution at ␣-carbon atom

Cyclopropane

730– 920 770– 725

800– 700 (m– s) 680– 650 (vs) 605– 550 3101– 3090 3038– 3019 1210– 1180 (s)

Cyclobutane

1001– 960 (vs)

Cyclopentane

900– 800 (s)

Cyclohexane

825– 815 (vs) 810– 795 (vs)

Cycloheptane

ca 733

Cyclooctane

ca 703

CH3 H C"C H

CH3 CH3

CH3 C"C H

Shifts to 1200 cm⫺1 for monoalkyl or 1,2-dialkyl substitution and to 1320 cm⫺1 for gem-1,1dialkyl substitution Shifts to 933 cm⫺1 for monoalkyl, to 887 cm⫺1 for cis-1,3-dialkyl, and to 891 cm⫺1 plus 855 cm⫺1 (doublet) for trans-1,3,-dialkyl substitution

Boat configuration Chair configuration

1392– 1377 450– 400 (vw) 270– 250 (m)

CH3 "C

CH3

Often a band at 530– 524 cm⫺1 indicates presence of adjacent tertiary and quaternary carbon atoms.

H

1380– 1379 492– 455 (vw) 220– 200 (m)

1372– 1368 970– 952 (m) 592– 545 (vw) 420– 400 (m) 310– 290 (m)

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TABLE 7.30 Raman Frequencies of Single Bonds to Hydrogen and Carbon (Continued) Group

Band, cm⫺1

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Remarks

Saturated C 9 H and C 9 C (continued) CH3

CH3 C"C CH3

H

CH3

CH3 C"C

CH3

CH3

C9C9C O C9C9

1385– 1375 522– 488 (w)

1392– 1386 690– 678 (m– s) 510– 485 (m) 424– 388 (w) 1170– 1100 (w– m) 600– 580 (m– s) 1120– 1090 (m– vs)

O

Tertiary or quaternary carbon adjacent to carbonyl group lowers the frequency 300 cm⫺1.

600– 510 (w– m) 9 CH 2 9 CO 9

1420– 1410 (s)

9 CHO

2850– 2810 (m) 2720– 2695 (vs)

Often appears as a shoulder

Unsaturated C 9 H 9C#C9H

3340– 3270 (w– m)

Alkyl substituents at higher frequencies; unsaturated or aryl substituents at lower frequencies

H 3040– 2995 (m)

C"C

H C"C H H

R C"C

H

Asymmetric " CH 2 stretch Symmetric " CH 2 stretch

1419– 1415 (m) 1309– 1288 (m)

Plus " CH and " CH stretching bands

1413– 1399 (m) 909– 885 (m) 711– 684 (w)

Plus " CH 2 stretching bands

H

H

R1 C"C

H

3095– 3050 (m) 2990– 2983 (s)

R2

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cap height base of text TABLE 7.30 Raman Frequencies of Single Bonds to Hydrogen and Carbon (Continued) Group

Band, cm⫺1

Remarks

Unsaturated C 9 H (continued) R1

R2 C"C

1270– 1251 (m)

Plus " CH stretching band

1314– 1290 (m)

Plus " CH stretching band

1360– 1322 (w) 830– 800 (vw)

Plus " CH stretching band

H

H R1

H C"C

H

R2 R3

R1 C"C R2

H Hydroxy O 9 H

Free 9 OH Intermolecularly bonded Aromatic 9 OH

3650– 3250 (w) 3400– 3300 (w) ca 3160 (s)

9 OH

1460– 1320 (w) 1276– 1205 (w– m) 1260 (w– m)

Common to all OH substituents Primary Secondary

C 9 C 9 OH primary

1070– 1050 (m– s) 1030– 960 (m– s) 480– 430 (w– m)

CCO stretching

C 9 C 9 OH Secondary

Tertiary

9 CO 9 O 9 H

CCO deformation

1135– 1120 (m– s) 825– 815 (vs) 500– 490 (w– m) 1210– 1200 (m– s) 755– 730 (vs) 360– 350 (w– m) 1305– 1270

CO stretching

N 9 H and C 9 N bonds Amine N9H Associated Nonbonded Salts 9 NH 2

3400– 3250 (s) 3550– 3250 (s) 2986– 2974 1650– 1590 (w– vs)

Primary amines show two bands. Often obscured by intense CH stretching bands Bending

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TABLE 7.30 Raman Frequencies of Single Bonds to Hydrogen and Carbon (Continued) Group

Band, cm⫺1

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Remarks

N 9 H and C 9 N Bonds (continued) Amides Primary

Secondary

3540– 3500 (w) 3400– 3380 (w) 1310– 1250 (s)

1150– 1095 (m) 3491– 3404 (m– s)

Both bands lowered ca 150 cm⫺1 in solid state and H bonding Interaction of NH bending and CN stretching; lowered 50 cm⫺1 in nonbonded state Rocking of NH 2 Two bands; lowered in frequency on H bonding and in solid state

1190– 1130 (m) 931– 865 (m– s) 430– 395 (w– m) 607– 555 (m)

C9N9C

1070– 1045 (m)

Stretching

Primary carbon Secondary ␣ carbon

1090– 1060 (m) 1140– 1035 (m)

Tertiary ␣ carbon

1240– 1020 (m)

CN stretching Two bands but often obscured. Strong band at 800 cm⫺1 Two bands. Strong band also at 745 cm⫺1

9

9 CO 9 N

O " CN bending

C C9N

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TABLE 7.31 Raman Frequencies of Triple Bonds Abbreviations Used in the Table m, moderately strong s– vs, strong to very strong m– s, moderate to strong vs, very strong s, strong Group

Band, cm⫺1

Remarks

R 9 C # CH

2160– 2100 (vs) 650– 600 (m) 356– 335 (s)

Monoalkyl substituted; C # C stretch C # CH deformation C # C 9 C bending of monoalkyls

R1 9 C # C 9 R2

2300– 2190 (vs)

C # C stretching of disubstituted alkyls; sometimes two bands

9C#C9C#C9

2264– 2251 (vs)

9C#N

2260– 2240 (vs) 2234– 2200 (vs) 840– 800 (s– vs) 385– 350 (m– s) 200– 160 (vs)

H9C#N Azides ⫺ ⫹ 9N9N#N

Diazonium salts ⫹ R9N#N Isonitriles ⫹ ⫺ 9N#C

Thiocyanates 9S9C#N

Unsaturated nonaryl substituents lower the frequency and enhance the intensity. Lowered ca 30 cm⫺1 with aryl and conjugated aliphatics CCCN symmetrical stretching Aliphatic nitriles

2094 (vs)

2170– 2080 (s) 1258– 1206 (s)

Asymmetric NNN stretching Symmetric NNN stretching; HN3 at 1300 cm⫺1

2300– 2240 (s)

2146– 2134 2124– 2109

Stretching of aliphatics Stretching of aromatics

2260– 2240 (vs) 650– 600 (s)

Stretching of C # N Stretching of SC

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TABLE 7.32 Raman Frequencies of Cumulated Double Bonds Abbreviations Used in the Table s, strong vs, very strong Group Allenes C"C"C

Carbodiimides (cyanamides) 9N"C"N9

Cumulenes (trienes) C"C"C"C

Isocyanates 9N"C"O

Isothiocyanates 9N"C"S

Ketenes C"C"O

Sulfinylamines R9N"S"O

vw, very weak w, weak

Band, cm⫺1

Remarks

2000– 1960 (s) 1080– 1060 (vs) 356

Pseudo-asymmetric stretching Symmetric stretching C " C " C bending

2140– 2125 (s) 2150– 2100 (vs) 1460 1150– 1140 (vs)

Asymmetric stretching of aliphatics Asymmetric stretching of aromatics; two bands Symmetrical stretching of aliphatics Symmetric stretching of aryls

2080– 2030 (vs) 878

2300– 2250 (vw) 1450– 1400 (s)

Asymmetric stretching Symmetric stretching

2220– 2100 690– 650

Two bands Alkyl derivatives

2060– 2040 (vs) 1130 (s) 1374 (s) 1120 (s)

Pseudo-asymmetric stretching Pseudo-symmetric stretching Alkyl derivatives Aryl derivatives

1306– 1214 (w) 1155– 989 (s)

Asymmetric stretching Symmetric stretching

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TABLE 7.33 Raman Frequencies of Carbonyl Bands Abbreviations Used in the Table m, moderately strong s– vs, strong to very strong m– s, moderate to strong vs, very strong s, strong w, weak Group Acid anhydrides 9 CO 9 O 9 CO 9 Saturated Conjugated, noncyclic

Acid fluorides 9 CO 9 F Alkyl Aryl Acid chlorides 9 CO 9 Cl Alkyl Aryl

Acid bromides 9 CO 9 Br Alkyl Aryl Acid iodides 9 CO 9 I Alkyl Aryl

Band, cm⫺1

1850– 1780 (m) 1771– 1770 (m) 1775 1720

1840– 1835 1812– 1800

1810– 1770 (s) 1774 1731

1812– 1788 1775– 1754

ca 1806 ca 1752

Lactones

1850– 1730 (s)

Esters Saturated

1741– 1725

Aryl and ␣,␤-unsaturated Diesters Oxalates Phthalates C # C 9 CO 9 O 9 Carbamates Aldehydes Ketones Saturated Aryl Alicyclic n⫽4 n⫽5 nⱖ6

Remarks

Alkyl branching on carbon adjacent to C " O lowers frequency by 5– 15 cm⫺1.

1727– 1714 1763– 1761 1738– 1728 1716– 1708 1694– 1688 1740– 1720 (s– vs)

1725– 1700 (vs) 1700– 1650 (m) 1782 (m) 1744 (m) 1725– 1699 (m)

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TABLE 7.33 Raman Frequencies of Carbonyl Bands (Continued) Band, cm⫺1

Group Carboxylic acids Mono-

Carboxylate ions

1690– 1550 (w) 1440– 1340 (vs) 1743– 1729 1600– 1570 (w)

Amino acid anion

Amides (see also Table 7.30) Primary Associated

Secondary Associated

Nonbonded Tertiary Lactams

These ␣-substituents increase the frequency: F, Cl, Br, OH. Solid state; often two bands In solution; very broad band

1782– 1645 1750– 1710 1743– 1729

Amino acids

Nonbonded

Remarks

1686– 1625 (s)

Poly-

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Often masked by water deformation band near 1630 cm⫺1

1686– 1576 (m– s) 1650– 1620 (m) 1715– 1675 (m) 1620– 1585 (m) 1680– 1630 (w) 1570– 1510 (w) 1490– 1440 1700– 1650 1550– 1500 1670– 1630 (m) 1750– 1700 (m)

Both cis and trans forms Trans form Cis form Both cis and trans forms Trans form (no cis band)

TABLE 7.34 Raman Frequencies of Other Double Bonds Abbreviations Used in the Table m, moderately strong vs, very strong m– s, moderate to strong w, weak s, strong s– vs, strong to very strong w– m, weak to moderately strong Group

Band, cm⫺1 Alkenes

C"C H

C"C

1680– 1576 (m– s)

General range

1648– 1638 (vs)

C " C stretching

R1 C"C

H

H

H

R1 C"C

H

Remarks

R2

ca 1650 (vs) 270– 252 (w)

C " C stretching C " C 9 C skeletal deformation

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TABLE 7.34 Raman Frequencies of Other Double Bonds (Continued) Band, cm⫺1

Group Alkenes R1

R2

(continued)

ca 1660 (vs) 970– 952 (w)

C"C H

C"C

Remarks

H

C " C stretching Asymmetric CC stretching

H

R1 C"C H

1676– 1665 (s)

C 9 C stretching

1678– 1664 (vs) 522– 488 (w)

C " C stretching C " C 9 C skeletal deformation

1680– 1665 (s) 690– 678 (m– s) 510– 485 (m) 424– 388 (w)

C " C stretching Symmetrical CC stretching Skeletal deformation Skeletal deformation

R2

R1

R3 C"C

R2

H

R1

R3 C"C

R2

R4

Haloalkene

X ⫽ fluorine

X ⫽ chlorine C"C

H 2C " CHX HXC " CHX cis trans H 2C " CX2 X2C " CHX X2C " CX2 Group

X ⫽ bromine

X-iodine

stretch of haloalkanes

1654

1603– 1601

1596– 1593

1581

1712 1694 1728 1792 1872

1590– 1587 1578– 1576 1616– 1611 1589– 1582 1577– 1571

1587– 1583 1582– 1581 1593 1552 1547

1543 1537

Band, cm⫺1

1465 (solid) Remarks

C " N 9 bonds Aldimines (azomethines) H C " N 9 R2 R1 Aldoximines and Ketoximes C " N 9 OH

Azines C"N9N"C

1673– 1639 1405– 1400 (s)

Dialkyl substituents at higher frequency; diaryl substituents at lower end of range

1680– 1617 (vs) 1335– 1330 (w)

1625– 1608 (s)

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TABLE 7.34 Raman Frequencies of Other Double Bonds (Continued) Band, cm⫺1

Group

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Remarks

C " N 9 bonds (continued) Hydrazones H H C"N9N R2 R1

1660– 1610 (s– vs)

Imido ethers O C " NH

1658– 1648

NH stretching at 3360– 3327 cm⫺1

Semicarbazones and thiosemicarbazones H NH2 C"N9N C

1665– 1642 (vs)

Aliphatic. Thiosemicarbazones fall in lower end of range. Aromatic derivatives

1620– 1610 (vs)

O (or S) Azo compounds 9 N " N 9 9N"N9

1580– 1570 (vs) 1442– 1380 (vs) 1060– 1030 (vs)

Nonconjugated Conjugated to aromatic ring CN stretching in aryl compounds

Nitro compounds N " O Alkyl nitrites

1660– 1620 (s)

N " O stretching

Alkyl nitrates

1635– 1622 (w– m) 1285– 1260 (vs) 610– 562 (m)

Asymmetric NO2 stretching Symmetric NO2 stretching NO2 deformation

Nitroalkanes Primary

1560– 1548 (m– s) 1395– 1370 (s) 915– 898 894– 873 618– 609 640– 615 494– 472

Secondary

(m– s) (m– s) (w) (w) (w– m)

1553– 1547 (m) 1375– 1360 (s) 908– 868 (m) 863– 847 (s) 625– 613 (m) 560– 516 (s)

Sensitive to substituents attached to CNO2 group

Shoulder Broad; useful to distinguish from secondary nitroalkanes

Sharp band

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TABLE 7.34 Raman Frequencies of Other Double Bonds (Continued) Band, cm⫺1

Group

Remarks

Nitro compounds N " O (continued) Nitroalkanes (continued) Tertiary

1543– 1533 (m) 1355– 1345 (s)

Nitrogen oxides ⫹

⫺

1612– 1602 (s) 1252 (m) 1049– 1017 (s) 835 (s) 541 (w) 469 (w)

N:O

TABLE 7.35 Raman Frequencies of Aromatic Compounds Abbreviations Used in the Table m, moderately strong var, of variable strength m– s, moderate to strong vs, very strong m– vs, moderate to very strong w, weak s, strong w– m, weak to moderately strong s– vs, strong to very strong Group

Band, cm⫺1

Remarks

Common features Aromatic compounds

3070– 3020 (s) 1630– 1570 (m– s)

CH stretching C 9 C stretching

Substitution patterns of the benzene ring Monosubstituted

1180– 1170 (w– m) 1035– 1015 (s) 1010– 990 (vs)

Characteristic feature; found also with 1,3- and 1,3,5-substitutions

630– 605 (w) 1,2-Disubstituted

1230– 1215 (m) 1060– 1020 (s) 740– 715 (m)

Characteristic feature Lowered 60 cm⫺1 for halogen substituents

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TABLE 7.35 Raman Frequencies of Aromatic Compounds (Continued) Group

Band, cm⫺1

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Remarks

Substitution patterns of the benzene ring (continued) 1,3-Disubstituted

1010– 990 (vs) 750– 640 (s)

1,4-Disubstituted

1230– 1200 (s– vs) 1180– 1150 (m) 830– 750 (vs) 650– 630 (m– w)

Isolated hydrogen

1,2,3-Trisubstituted

1379 (s– vs) 1290– 1200 (s) 745– 670 (m– vs) 580– 480 (s) 1100– 1050 (m) 670– 500 (vs)

Characteristic feature

Lower frequency with Cl substituents

Characteristic feature

The lighter the mass of the substituent, the higher the frequency.

490– 430 (w) 1,2,4-Trisubstituted

1,3,5-Trisubstituted Completely substituted

750– 650 (vs) 580– 540 (var) 500– 450 (var)

Lighter mass at higher frequencies

1010– 990 (vs) 1296 (s) 550 (vs) 450 (m) 361 (m) Other aromatic compounds

Naphthalenes

Disubstituted naphalenes

Anthracenes

1390– 1370 1026– 1012 767– 762 535– 512 519– 512 773– 737 (s) 726– 705 (s) 690– 634 (s) 608 575– 569 544– 537 1415– 1385

Ring breathing ␣ or ␤ substituents ␤ substituents ␣ substituents ␤ substituents 1,2-; 1,3-; 2,3-; 2,6-; 2,71,3-; 1,4-(two bands); 1,6-; 1,7-(two bands) 1,2-; 1,4-(two bands); 1,5-; 1,8-(two bands) 1,31,2-; 1,3-; 1,61,2-; 1,7-; 1,8Ring breathing

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TABLE 7.36 Raman Frequencies of Sulfur Compounds Abbreviations Used in the Table m, moderately strong s– vs, strong to very strong m– s, moderate to strong vs, very strong s, strong w– m, weak to moderately strong Group 9S9H C"S

S"O In (RO2 )2SO In (R2 N)2SO In R2SO SOF2 SOCl2 SOBr2

Band, cm⫺1

Remarks

2590– 2560 (s)

SH stretching for both aliphatic and aromatic

1065– 1050 (m) 735– 690 (vs)

Solid state

1209– 1198 1108 1070– 1010 (w– m) 1308 1233 1121

One or two bands Broad

9 SO2 9

1330– 1260 (m– s) 1155– 1110 (s) 610– 540 (m) 512– 485 (m)

Asymmetric SO2 stretching Symmetric SO2 stretching Scissoring mode of aryls Scissoring mode of alkyls

9 SO2 9 N

ca 1322 (m) 1163– 1138 (s) 524– 510 (s)

Asymmetric SO2 stretching Symmetric SO2 stretching Scissoring mode

9 SO2 9 O

1363– 1338 (w– m)

SO2 stretching. Aryl substituents occur at higher range.

1192– 1165 (vs) 589– 517 (w– m)

9 SO2 9 S 9

1334– 1305 (m– s) 1128– 1126 (s) 559– 553 (m– s)

X 9 SO2 9 X

1412– 1361 (w– m) (F) (Cl) 1263– 1168 (s) (F) (Cl) 596– 531 (s)

9 O 9 SO2 9 O 9

1388– 1372 (s) 1196– 1188 (vs)

9O9C9S9

Scissoring (two bands). Aryl substituents occur at higher range of frequencies.

670– 620 (vs) 480– 450 (vs)

C " S stretching CS stretching

920 (m) 850– 820 (m)

C 9 SH deformation of aryls

S C 9 SH

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TABLE 7.36 Raman Frequencies of Sulfur Compounds (Continued) Group C9S9

Band, cm⫺1 752 (vs), 731 (vs) 742– 722 (m– s) 698 (w), 678 (s) 693– 639 (s) 651– 610 (s– vs) 589– 585 (vs)

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Remarks With vinyl group attached With CH 3 attached With allyl group attached Ethyl or longer alkyl chain Isopropyl group attached tert-Butyl group attached

(CH2)n S n⫽2 n⫽4 n⫽5

1112 688 659

C 9 (S 9S)n 9 C Didi-n-alkyl disulfides Di-tert-butyl disulfide Trisulfides

715– 620 (vs) 525– 510 (vs) 576 (s) 543 (m) 510– 480 (s)

Two bands; CS stretching Two bands; SS stretching CS stretching SS stretching SS stretching

TABLE 7.37 Raman Frequencies of Ethers Abbreviations Used in the Table m, moderately strong var, of variable strength s, strong vs, very strong Group C9O9C Aliphatic

Aromatic

C9O9C9O9C

Band, cm⫺1

Remarks

1200– 1070 (m)

Asymmetrical COC stretching. Symmetrical substitution gives higher frequencies Symmetrical COC stretching Braching at ␣ carbon gives higher frequencies.

930– 830 (s) 800– 700 (s) 550– 400 1310– 1210 (m) 1050– 1010 (m)

1145– 1129 (m) 900– 800 (vs) 537– 370 (s) 396– 295

C

C

1280– 1240 (s)

Ring breathing

O 9O9O9

800– 770 (var)

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TABLE 7.37 Raman Frequencies of Ethers (Continued) Band, cm⫺1

Group

Remarks

(CH2)n O n⫽3 n⫽4 n⫽5

1040– 1010 (s) 920– 900 (s) 820– 800 (s)

TABLE 7.38 Raman Frequencies of Halogen Compounds Abbreviations Used in the Table m– s, moderate to strong var, of variable strength s, strong vs, very strong Group C9F

Band, cm⫺1 1400– 870

C 9 Cl Primary Secondary Tertiary

350– 290 (s) 660– 650 (vs) 760– 605 (s) 620– 540 (var)

" C 9 Cl

844– 564 438– 396 381– 170

" CCl2

601– 441 300– 235

C 9 Br

690– 490 (s)

Remarks Correlations of limited applicability because of vibrational coupling with stretching CCCl bending; general May be one to four bands May be one to three bands

Often several bands; primary at higher range of frequencies. Tertiary has very strong band at ca 520 cm⫺1.

305– 258 (m– s) " C 9 Br

745– 565 356– 318 240– 115

" CBr2

467– 265 185– 145

C9I

663– 595 309 154– 85

"C9I

ca 180

Solid state

" CI 2

ca 265 ca 105

Solid state Solid state

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TABLE 7.39 Raman Frequencies of Miscellaneous Compounds Abbreviations Used in the Table m, moderately strong s, strong Group C 9 As C 9 Pb C 9 Hg C 9 Si C 9 Sn P9H

vs, very strong vvs, very very strong

Band, cm⫺1

Remarks

570– 550 (vs) 240– 220 (vs) 480– 420 (s) 570– 510 (vvs) 1300– 1200 (s) 600– 450 (s) 2350– 2240 (m)

CAs stretching CAsC deformation CPb stretching CHg stretching CSi stretching CSn stretching PH stretching

Heterocyclic rings Trimethylene oxide Trimethylene imine Tetrahydrofuran Pyrrolidine 1,3-Dioxolane 1,4-Dioxane Piperidine Tetrahydropyran Morpholine Piperazine Furan Pyrazole Pyrrole Thiophene

Pyridine

1029 1026 914 899 939 834 815 818 832 836 1515– 1460 1140 1040– 990 1420– 1360 (vs) 1144 1410 (s) 1365 (s) 1085 (vs) 1035 (s) 832 (vs) 610 (s) 1030 (vs) 990 (vs)

2-Substituted

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TABLE 7.40 Principal Argon-Ion Laser Plasma Lines

Wavelength, nm 487.9860 488.9033 490.4753 493.3206 496.5073 497.2157 500.9334 501.7160 506.2036 514.1790 514.5319 516.5774 517.6233 521.6816 528.6895 539.7522 545.4307 555.8703 560.6734 565.0705 565.4450 569.1650 577.2326 581.2746 598.5920 610.3546 611.4929 612.3368 613.8660 617.2290 624.3125 639.9215 641.6308

Wavenumber, cm⫺1 20 20 20 20 20 20 19 19 19 19 19 19 19 19 18 18 18 17 17 17 17 17 17 17 16 16 16 16 16 16 16 15 15

486.67 448.23 382.70 265.13 135.07 106.39 957.16 926.03 749.39 443.06 429.73 352.79 313.69 163.44 909.43 521.87 329.04 984.81 830.75 692.00 680.28 564.73 319.24 198.80 701.24 379.38 348.90 326.36 285.69 196.96 013.19 622.60 580.98

Relative intensity

Shift relative to 488.0 nm, cm⫺1

Shift relative to 514.5 nm, cm⫺1

5000 200 130 970 960 330 1500 620 1400 360 1000 38 41 20 150 18 19 30 48 29 27 27 69 49 23 91 1750 100 97 1400 590 160 50

0 38.4 104.0 221.5 351.6 380.3 529.5 560.6 737.3 1043.6 1056.9 1133.9 1173.0 1323.2 1577.2 1964.8 2157.6 2501.9 2655.9 2794.7 2806.4 2921.9 3167.4 3287.9 3785.4 4107.3 4137.8 4160.3 4201.0 4289.7 4473.5 4864.1 4905.7

0 76.9 116.0 266.3 520.3 907.9 1100.7 1444.9 1599.0 1737.7 1749.4 1865.0 2110.5 2230.9 2728.5 3050.4 3080.8 3103.4 3144.0 3232.8 3416.5 3807.1 3848.8

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NUCLEAR MAGNETIC RESONANCE

TABLE 7.41 Nuclear Properties of the Elements In the following table the magnetic moment ␮ is in multiples of the nuclear magneton ␮N(eh/4␲Mc) with diamagnetic correction. The spin I is in multiples of h/2␲, and the electric quadrupole moment Q is in multiples of 10⫺28 square meters. Nuclei with spin 1⁄2 have no quadrupole moment. Sensitivity is for equal numbers of nuclei at constant field. NMR frequency at any magnetic field is the entry for column 5 multiplied by the value of the magnetic field in kilogauss. For example, in a magnetic field of 23.490 kG, protons will process at 4.2576 ⫻ 23.490 kG ⫽ 100.0 MHz. Radionuclides are denoted with an asterisk. The data were extracted from M. Lederer and V. S. Shirley, Table of Isotopes, 7th ed., Wiley-Interscience, New York, 1978; A. H. Wapstra and G. Audi, “The 1983 Atomic Mass Evaluation,” Nucl. Phys. A432:1– 54 (1985); V. S. Shirley, ed., Table of Radioactive Isotopes, 8th ed., Wiley-Interscience, New York, 1986; and P. Raghavan, “Table of Nuclear Moments,” At. Data Nucl. Data Tables, 42:189 (1989).

Nuclide 1

n H 2 H 3 H 3 He 6 Li 7 Li 9 Be 10 B 11 B 13 C 14 N 15 N 17 O 19 F 21 Ne 22 Na 23 Na 25 Mg 27 Al 29 Si 31 P 33 S 35 S 35 Cl 36 Cl 37 Cl 37 Ar 39 K 40 K 41 K 43 Ca 45 Sc 47 Ti 49 Ti 50 V 1

Natural abundance, % * 99.985 0.015 * 0.0001 7.5 92.5 100 19.9 80.1 1.10 99.634 0.366 0.038 100 0.27 * 100 10.00 100 4.67 100 0.75 * 75.77 * 24.23 * 93.258 0.0117 6.730 0.135 100 7.3 5.5 0.250

Spin I ⁄ ⁄ 1 1⁄2 1⁄2 1 3⁄2 3⁄2 3 3⁄2 1⁄2 1 1⁄2 5⁄2 1⁄2 3⁄2 3 3⁄2 5⁄2 5⁄2 1⁄2 1⁄2 3⁄2 3⁄2 3⁄2 2 3⁄2 3⁄2 3⁄2 4 3⁄2 7⁄2 7⁄2 5⁄2 7⁄2 6 12 12

Sensitivity at constant field relative to 1 H 0.321 39 1.000 00 0.009 65 1.213 54 0.442 12 0.008 50 0.293 55 0.013 89 0.019 85 0.165 22 0.015 91 0.001 01 0.001 04 0.029 10 0.834 00 0.002 46 0.018 1 0.092 70 0.002 68 0.206 89 0.007 86 0.066 52 0.002 27 0.008 50 0.004 72 0.012 1 0.002 72 0.012 76 0.000 51 0.005 23 0.000 084 0.006 42 0.302 44 0.002 10 0.003 78 0.055 71

NMR frequency for a 1-kG field, MHz

Magnetic moment ␮ /␮N, J · T⫺1

2.916 39 4.257 64 0.653 57 4.541 37 3.243 52 0.626 60 1.654 78 0.598 6 0.457 51 1.366 26 1.070 81 0.307 76 0.431 72 0.577 41 4.007 65 0.336 30 0.443 4 1.126 86 0.260 82 1.110 28 0.846 53 1.725 10 0.327 16 0.508 0.417 64 0.489 3 0.347 64 0.581 8 0.198 93 0.247 37 0.109 19 0.286 88 1.035 88 0.240 40 0.240 47 0.425 04

⫺1.913 043 2.792 847 0.857 438 2.978 963 ⫺2.127 624 0.822 047 3.256 427 ⫺1.177 9 1.800 645 2.688 649 0.702 412 0.403 761 ⫺0.283 189 ⫺1.893 80 2.628 867 ⫺0.661 797 1.745 2.217 522 ⫺0.855 46 3.641 504 ⫺0.555 29 1.131 60 0.643 821 1.00 0.821 874 1.283 8 0.684 124 1.145 0.391 466 ⫺1.298 099 0.214 870 ⫺1.317 26 4.756 483 ⫺0.788 48 ⫺1.104 17 3.345 689

Electric quadrupole moment Q, 10⫺28 m2

0.002 860

0.000 82 ⫺0.040 1 0.052 88 0.084 59 0.040 59 0.020 2 ⫺0.025 58 0.101 55 0.108 9 0.199 4 0.140 3 ⫺0.067 8 0.045 ⫺0.081 65 ⫺0.016 8 ⫺0.064 35 0.060 1 ⫺0.074 9 0.073 3 ⫺0.0408 ⫺0.22 0.29 0.24 0.21

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TABLE 7.41 Nuclear Properties of the Elements (Continued)

Nuclide 51

V Cr 55Mn 57Fe 59 Co 61 Ni 63 Cu 65 Cu 67 Zn 69 Ga 71 Ga 73 Ge 75 As 77 Se 79 Br 81 Br 83 Kr 85 Rb 87 Rb 87 Sr 89 Y 91 Zr 93 Nb 95 Mo 97 Mo 99 Tc 99 Ru 101 Ru 103 Rh 105 Pd 107 Ag 109 Ag 111 Cd 113 Cd 113 In 115 In 115 Sn 117 Sn 119 Sn 121 Sb 123 Sb 123 Te 125 Te 127 I 129 Xe 131 Xe 133 Cs 135 Ba 137 Ba 138 La 53

Natural abundance, % 99.750 9.501 100 2.1 100 1.140 69.17 30.83 4.1 60.108 39.892 7.73 100 7.63 50.69 49.31 11.5 72.165 27.835 7.00 100 11.22 100 15.92 9.55 * 12.7 17.0 100 22.33 51.839 48.161 12.80 12.22 4.3 95.7 0.34 7.68 8.59 57.36 42.64 0.908 7.139 100 26.4 21.2 100 6.592 11.23 * 0.0902

Spin I

Sensitivity at constant field relative to 1H

NMR frequency for a 1-kG field, MHz

Magnetic moment ␮ /␮N, J · T⫺1

⁄ ⁄ 5⁄2 1⁄2 7⁄2 3⁄2 3⁄2 3⁄2 5⁄2 3⁄2 3⁄2 9⁄2 3⁄2 1⁄2 3⁄2 3⁄2 9⁄2 5⁄2 3⁄2 9⁄2 1⁄2 5⁄2 9⁄2 5⁄2 5⁄2 9⁄2 5⁄2 5⁄2 1⁄2 5⁄2 1⁄2 1⁄2 1⁄2 1⁄2 9⁄2 9⁄2 1⁄2 1⁄2 1⁄2 5⁄2 7⁄2 1⁄2 1⁄2 5⁄2 1⁄2 3⁄2 7⁄2 3⁄2 3⁄2 5

0.383 60 0.000 91 0.178 81 0.000 03 0.278 41 0.003 59 0.093 42 0.114 84 0.002 87 0.069 71 0.143 00 0.001 41 0.025 36 0.007 03 0.079 45 0.099 51 0.001 90 0.010 61 0.177 03 0.002 72 0.000 12 0.009 49 0.488 21 0.003 27 0.003 49 0.381 74 0.001 13 0.001 59 0.000 03 0.001 13 0.000 066 9 0.000 101 0.009 66 0.011 06 0.351 21 0.353 48 0.035 61 0.046 05 0.052 73 0.163 02 0.046 59 0.018 37 0.032 20 0.095 40 0.021 62 0.002 82 0.048 38 0.005 00 0.006 97 0.094 04

1.121 30 0.241 14 1.057 60 0.138 15 1.007 7 0.381 13 1.129 79 1.210 27 0.266 93 1.024 75 1.302 04 0.148 97 0.731 48 0.815 66 1.070 39 1.153 81 0.164 42 0.412 53 1.398 07 0.185 24 0.209 49 0.397 47 1.045 20 0.278 74 0.284 62 0.963 0.195 53 0.219 2 0.134 76 0.195 7 0.173 30 0.199 24 0.906 89 0.948 68 0.936 52 0.938 54 1.400 74 1.526 06 1.596 56 1.025 49 0.555 30 1.123 46 1.354 51 0.857 76 1.186 01 0.351 58 0.562 32 0.425 81 0.476 33 0.566 14

5.148 706 ⫺0.474 54 3.468 72 0.090 623 4.627 ⫺0.750 02 2.223 29 2.381 67 0.875 479 2.016 59 2.562 27 ⫺0.879 468 1.439 475 0.535 042 2.106 399 2.270 562 ⫺0.970 669 1.353 03 2.751 24 ⫺1.093 603 ⫺0.137 415 ⫺1.303 62 6.170 5 ⫺0.914 2 ⫺0.933 5 5.684 7 ⫺0.641 3 ⫺0.718 8 ⫺0.088 40 ⫺0.642 ⫺0.113 680 ⫺0.130 691 ⫺0.594 886 ⫺0.622 301 5.528 9 5.540 8 ⫺9.18 84 ⫺1.001 05 ⫺1.047 28 3.363 4 2.549 8 ⫺0.736 948 ⫺0.888 505 2.813 327 ⫺0.777 976 0.691 862 2.582 025 0.837 943 0.937 365 3.713 646

72 32

Electric quadrupole moment Q, 10⫺28 m2 ⫺0.052 ⫺0.15 0.33 0.42 0.162 ⫺0.220 ⫺0.204 0.150 0.170 0.100 ⫺0.173 0.314 0.331 0.276 0.253 0.274 0.132 0.335 ⫺0.206 ⫺0.32 ⫺0.022 ⫺0.255 ⫺0.129 0.079 0.457 0.660

0.799 0.81

⫺0.36 ⫺0.49 ⫺0.789 ⫺0.12 ⫺0.003 7 0.160 0.245 0.45

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TABLE 7.41 Nuclear Properties of the Elements (Continued)

Nuclide 139

La Ce 139Ce 141Ce 141 Pr 143 Nd 145 Nd 143 Pm 147 Pm 147 Sm 149 Sm 151 Eu 153 Eu 155 Gd 157 Gd 159 Tb 161 Dy 163 Dy 165 Ho 167 Er 169 Tm 171 Yb 173 Yb 175 Lu 176 Lu 177 Hf 179 Hf 180 Ta 181 Ta 183 W 185 Re 187 Re 187 Os 189 Os 191 Ir 193 Ir 195 Pt 197 Au 199 Hg 201 Hg 203 Tl 205 Tl 207 Pb 209 Bi 229 Th 231 Pa 235 U 237 Np 239 Pu 243 Am 137

Natural abundance, % 99.9098 * * * 100 12.18 8.30 * * 15.0 13.8 47.8 52.2 14.80 15.65 100 18.9 24.9 100 22.95 100 14.3 16.12 97.41 * 2.59 18.606 13.629 0.012 99.988 14.3 37.40 * 62.60 1.6 16.1 37.3 62.7 33.8 100 16.87 13.18 29.524 70.476 22.1 100 * * * 0.7200 * * *

Spin I ⁄ ⁄ 3⁄2 7⁄2 5⁄2 7⁄2 7⁄2 5⁄2 7⁄2 7⁄2 7⁄2 5⁄2 5⁄2 3⁄2 3⁄2 3⁄2 5⁄2 5⁄2 7⁄2 7⁄2 1⁄2 1⁄2 5⁄2 7⁄2 7 7⁄2 9⁄2 9 7⁄2 1⁄2 5⁄2 5⁄2 1⁄2 3⁄2 3⁄2 3⁄2 1⁄2 3⁄2 1⁄2 3⁄2 1⁄2 1⁄2 1⁄2 9⁄2 5⁄2 3⁄2 7⁄2 5⁄2 1⁄2 5⁄2 72 32

Sensitivity at constant field relative to 1H 0.060 58 0.006 41 0.006 41 0.003 64 0.334 83 0.003 39 0.000 79 0.235 10 0.049 40 0.001 52 0.000 85 0.179 29 0.015 44 0.000 15 0.000 33 0.069 45 0.000 48 0.001 30 0.204 23 0.000 507 0.000 566 0.005 52 0.001 35 0.031 28 0.039 75 0.001 40 0.000 55 0.102 51 0.037 44 0.000 08 0.138 70 0.143 00 0.000 01 0.002 44 0.000 03 0.000 04 0.010 39 0.000 03 0.005 94 0.001 49 0.195 981 0.201 82 0.009 55 0.144 33 0.000 42 0.069 03 0.000 15 0.132 64 0.000 38 0.017 88

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NMR frequency for a 1-kG field, MHz

Magnetic moment ␮ /␮N, J · T⫺1

0.606 10 0.462 0.462 0.237 1.303 55 0.231 9 0.142 9 1.16 0.57 0.177 47 0.146 31 1.058 54 0.467 44 0.131 7 0.1727 1.023 1.465 3 0.205 07 0.908 81 0.122 81 3.531 0.752 59 0.207 301 0.486 24 0.345 1 0.172 81 0.108 56 0.404 0.516 25 0.179 56 0.971 7 0.981 7 0.098 56 0.335 35 0.076 6 0.0832 0.929 20 0.074 06 0.771 21 0.284 68 2.473 10 2.497 42 0.903 38 0.696 28 0.140 1.02 0.083 0.957 0.309 0.491

2.783 045 0.91 0.91 1.09 4.275 4 ⫺1.065 ⫺0.656 3.8 2.6 ⫺0.814 9 ⫺0.671 8 3.471 8 1.533 1 ⫺0.259 1 ⫺0.339 9 2.014 ⫺0.480 6 0.672 6 4.173 ⫺0.563 9 ⫺0.231 6 0.493 67 ⫺0.679 89 2.232 7 3.169 0.793 5 ⫺0.640 9 4.77 2.3705 0.117 785 3.1871 3.219 7 0.064 652 0.659 933 0.150 7 0.163 7 0.609 52 0.145 746 0.505 885 ⫺0.560 226 1.622 258 1.638 215 0.592 58 4.110 6 0.46 2.01 ⫺0.38 3.14 0.203 1.61

Electric quadrupole moment Q, 10⫺28 m2 0.20

⫺0.059 ⫺0.63 ⫺0.33 0.70 ⫺0.26 0.094 0.903 2.41 1.27 1.35 1.432 2.47 2.65 3.58 3.57

2.80 3.49 4.97 3.36 3.79 3.17 2.18 2.07 0.856 0.816 0.751 0.547 0.386

⫺0.50 4.30 ⫺1.72 4.936 3.886 4.21

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TABLE 7.42 Proton Chemical Shifts Values are given on the officially approved ␦ scale; ␶ ⫽ 10.00 ⫺ ␦. Abbreviations Used in the Table R, alkyl group Ar, aryl group Substituent group

Methyl protons

Methylene protons

Methine proton

HC 9 C 9 CH 2 HC 9 C 9 NR 2 HC 9 C 9 C " C HC 9 C 9 C " O HC 9 C 9 NRAr HC 9 C 9 H(C " O)R HC 9 C 9 (C " O)NR 2 HC 9 C 9 (C " O)Ar HC 9 C 9 (C " O)OR HC 9 C 9 Ar HC 9 C 9 OH HC 9 C 9 OR HC 9 C 9 C # CR HC 9 C 9 C # N HC 9 C 9 SR HC 9 C 9 OAr HC 9 C 9 O(C " O)R HC 9 C 9 SH HC 9 C 9 (S " O)R and HC 9 C 9 SO2 R HC 9 C 9 NR 3⫹ HC 9 C 9 O 9 N " O HC 9 C 9 O(C " O)CF3 HC 9 C 9 CL HC 9 C 9 F HC 9 C 9 NO2 HC 9 C 9 O(C " O)Ar HC 9 C 9 I HC 9 C 9 Br

0.95 1.05 1.00 1.05 1.10 1.10 1.10 1.15 1.15 1.15 1.20 1.20 1.20 1.25 1.25 1.30 1.30 1.30 1.35

1.20 1.45 1.35 1.55 1.50 1.50 1.50 1.55 1.70 1.55 1.50 1.50 1.50 1.65 1.60 1.55 1.60 1.60 1.70

1.55 1.70 1.70 1.95 1.80 1.90 1.80 1.90 1.90 1.80 1.75 1.75 1.80 2.00 1.90 2.00 1.80 1.65

1.40 1.40 1.40 1.55 1.55 1.60 1.65 1.75 1.80

1.75

2.05

1.65 1.80 1.85 2.05 1.75 1.80 1.85

1.95 2.15 2.50 1.85 2.10 1.90

HC 9 CH 2 HC 9 C " C HC 9 C # C HC 9 (C " O)OR HC 9 (C " O)NR 2 HC 9 SR HC 9 O 9 O HC 9 (C " O)R HC 9 C # N HC 9 I HC 9 CHO HC 9 Ar HC 9 NR 2 HC 9 SSR HC 9 (C " O)Ar HC 9 SAr HC 9 NRAr HC 9 SO2 R and HC 9 (SO)R HC 9 Br HC 9 NR 3⫹

0.90 1.60 1.70 2.00 2.00 2.05 2.10 2.10 2.15 2.15 2.20 2.25 2.25 2.35 2.40 2.40 2.60 2.60 2.70 2.95

1.30 2.05 2.20 2.25 2.25 2.55 2.30 2.35 2.45 3.15 2.40 2.45 2.40 2.70 2.70 3.10 3.05 3.40 3.10

1.50 2.80 2.50 2.40 3.00 2.55 2.65 2.90 4.25 2.85 2.80 3.40 3.60 4.10 3.60

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TABLE 7.42 Proton Chemical Shifts (Continued) Substituent group HC 9 NH(C " O)R HC 9 SO3 R HC 9 Cl HC 9 OH and HC 9 OR HC 9 PAr3 HC 9 NH 2 HC 9 O(C " O)R HC 9 OAr HC 9 O(C " O)Ar HC 9 O(C " O)CF1 HC 9 F HC 9 NO2

Methyl protons

Methylene protons

Methine proton

2.95 2.95 3.05 3.20 3.20 3.50 3.65 3.80 3.80 3.95 4.25 4.30

3.35

3.85

3.45 3.40 3.40 3.75 4.10 4.00 4.20 4.30 4.50 4.35

4.05 3.60

0.20 2.45 1.65 1.50 1.25

0.40

Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane

Substituent group HC # CH HC # CAr HC # C 9 C " C HAr HCO 9 O HCO 9 R HCO 9 Ar HO 9 N " C (oxime)

Proton shift 2.35 2.90 2.75 7.20 8.1 9.4– 10.0 9.7– 10.5 9– 12

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Substituent group HO 9 C " O HO 9 SO2 HO 9 Ar HO 9 R HS 9 Ar HS 9 R HN 9 Ar HN 9 R

4.05 4.95 4.60 5.05 4.80 4.60

1.80

Proton shift 10– 12 11– 12 4.5– 6.5 0.5– 4.5 2.8– 3.6 1– 2 3– 6 0.5– 5

Saturated heterocyclic ring systems

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TABLE 7.42 Proton Chemical Shifts (Continued) Unsaturated cyclic systems

TABLE 7.43 Estimation of Chemical Shift for Protons of 9 CH 2 9 and Methine Groups

␦CH2 ⫽ 0.23 ⫹ C1 ⫹ C2

␦CH ⫽ 0.23 ⫹ C1 ⫹ C2 ⫹ C3

X*

C

X*

C

X*

C

9 CH 3 9 CF3 C"C 9C#C9R 9 COOR 9 NR 2 9 CONR 2

0.5 1.1 1.3 1.4 1.5 1.6 1.6

9 SR 9 C # C 9 Ar 9 CN 9 CO 9 R 9I 9 Ph 9 Br

1.6 1.7 1.7 1.7 1.8 1.8 2.3

9 OR 9 Cl 9 OH 9N"C"S 9 OCOR 9 OPh

2.4 2.5 2.6 2.9 3.1 3.2

* R, alkyl group; Ar, aryl group; Ph, phenyl group.

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TABLE 7.44 Estimation of Chemical Shift for Proton Attached to a Double Bond Positive Z values indicate a downfield shift, and an arrow indicates the point of attachment of the substituent group to the double bond. Rcis ⫽ 5.25 ⫺ Zgem ⫹ Zcis ⫹ Ztrans

dC " C

Rtrans

H

H C"C Tgem

R

Zgem , ppm

Zcis , ppm

Ztrans , ppm

:H :alkyl :alkyl 9 ring (5- or 6-member) :CH 2O 9 :CH 2S 9 :CH 2 X (X: F, Cl, Br) CH2N

0 0.45 0.69 0.64 0.71 0.70 0.58

0 ⫺0.22 ⫺0.25 ⫺0.01 ⫺0.13 0.11 ⫺0.10

0 ⫺0.28 ⫺0.28 ⫺0.02 ⫺0.22 ⫺0.04 ⫺0.08

C " C (isolated)

1.00

⫺0.09

⫺0.23

C " C (conjugated)

1.24

0.02

⫺0.05

0.27 0.47

0.75 0.38

0.55 0.12

C " O (isolated)

1.10

1.12

0.87

C " O (conjugated)

1.06

0.91

0.74

:COOH (isolated) :COOH (conjugated) :COOR (isolated) :COOR (conjugated) H

0.97 0.80 0.80 0.78

1.41 0.98 1.18 1.01

0.71 0.32 0.55 0.46

1.02

0.95

1.17

1.37

0.98

0.46

1.11 1.22 1.21 2.11

1.46 ⫺1.07 ⫺0.60 ⫺0.35

1.01 ⫺1.21 ⫺1.00 ⫺0.64

0.69 1.05 1.54 1.08 1.07 1.14 0.80

⫺0.08 ⫺0.29 ⫺0.40 0.18 0.45 0.81 ⫺1.26

⫺0.06 ⫺0.32 ⫺1.02 0.13 0.55 0.88 ⫺1.21

1.17

⫺0.53

⫺0.99

:C # N :C # C 9

C"O N C"O Cl C"O :OR (R: aliphatic) :OR (R: conjugated) :OCOR CH2 9 C " O;

CH2 9 C # N

:CH 2 9 aromatic ring :F :Cl :Br :I :N 9 R (R: aliphatic) N 9 R (R: conjugated)

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TABLE 7.44 Estimation of Chemical Shift for Proton Attached to a Double Bond (Continued) R

Zgem , ppm

Zcis , ppm

Ztrans , ppm

2.08 1.38 0.66 1.65 1.11 1.55

⫺0.57 0.36 0.61 0.19 ⫺0.29 1.16

⫺0.72 ⫺0.07 0.32 0.09 ⫺0.13 0.93

N9C"O :aromatic :CF3 :aromatic (o-substituted) :SR :SO2

TABLE 7.45 Chemical Shifts in Monosubstituted Benzene

␦ ⫽ 7.27 ⫹ ⌬ i Substituent

⌬ ortho

⌬ meta

⌬ para

NO2 CHO COOH COOCH 3 COCl CCl 3 COCH 3 CN CONH 2 ⫹ NH 3 CH 2 X* CH 3 CH 2CH 3 CH(CH 3 )2 C(CH 3 )2 F Cl Br I NH 2 OCH 3 OH OCOR NHCH 3 N(CH 3 )2

0.94 0.58 0.80 0.71 0.82 0.8 0.62 0.26 0.65 0.4 0.0– 0.1 ⫺0.16 ⫺0.15 ⫺0.14 ⫺0.09 ⫺0.30 0.01 0.19 0.39 ⫺0.76 ⫺0.46 ⫺0.49 ⫺0.2 ⫺0.8 ⫺0.60

0.18 0.20 0.16 0.08 0.21 0.2 0.10 0.18 0.20 0.2 0.0– 0.1 ⫺0.09 ⫺0.06 ⫺0.09 0.05 ⫺0.02 ⫺0.06 ⫺0.12 ⫺0.25 ⫺0.25 ⫺0.10 ⫺0.13 0.1 ⫺0.3 ⫺0.10

0.39 0.26 0.25 0.20 0.35 0.2 0.25 0.30 0.22 0.2 0.0– 0.1 ⫺0.17 ⫺0.18 ⫺0.18 ⫺0.23 ⫺0.23 ⫺0.08 ⫺0.05 ⫺0.02 ⫺0.63 ⫺0.41 ⫺0.2 ⫺0.2 ⫺0.6 ⫺0.62

* X ⫽ Cl, alkyl, OH, or NH2 .

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TABLE 7.46 Proton Spin Coupling Constants Structure

J, Hz

H

Structure

12– 15

H (free rotation)

CH 9 CH CH 9 OH CH 9 NH

(no exchange)

5

S

6– 8 5 4– 8

H CH 9 C " O

H

1– 3 H

H 9N"C

8– 16 H

Ht

Hg gem cis C"C H

Hc Hc

CH C"C

trans cis trans

Hg gem C " CH 9 CH " C " CH 9 C " O Ht

0– 3 6– 14 11– 18 0.5– 3 0.5– 3 4– 10 10– 13 6

H Cyclopentane cis trans Cyclobutane cis trans Cyclopropane cis trans gem o H m p H 2 3

CH 9 C # CH H H 3-member 4-member C"C 5-member (ring) 6-member 7-member cis O trans gem cis S trans gem H cis N trans gem 2– 3 4 3 3– 4 5 2 2– 4 O 2– 5

0– 3 0– 3 0– 2 2– 4 5– 7 6– 9 10– 13 4– 5 3 5– 6 0 7 6 2 6 4 1.8 3.5 0– 1 1– 2

a– a a– e e– e

8– 10 2– 3 2– 3 4– 6 4– 6 8 8 9– 11 6– 8 4– 6 6– 10 1– 3 0– 1

1

H 9 CH2 9 C # C 9 CH

5– 6 3.5– 5.0 1.5 3.4 6– 12 4– 8 1.5– 2.5 2.5 1.5 0

3

6– 8

CH 9 SH

J, Hz

2– 3 3– 4 2 2– 4 2– 5 o F m p H o CH3 m p F H

4

C

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4 5

3

6

2

N

4

3

5

2

N H

1– 2 2– 3

8– 9 6

2– 3 3– 4 2– 4 3– 5 2– 5 2– 6

5– 6 7– 9 1– 2 1– 2 0– 1 0– 1

1– 2 1– 3 2– 3 3– 4 2– 4 2– 5

2– 3 2– 3 2– 3 3– 4 1– 2 1– 3

H C

45– 52 F gauche trans Hg gem cis C"C F trans

CH 9 CF Ht Hc

0– 12 10– 45 72– 90 ⫺3 to 20 12– 40

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TABLE 7.46 Proton Spin Coupling Constants (Continued) Structure

J, Hz

Structure

J, Hz

HC # CF C"C F

21 Fa

2– 4 CH3

Fe

CF C"C

冎

He

0– 6 Ha

H

a– a a– e e– e e– e

34 12 ⬍5– 8

TABLE 7.47 Proton Chemical Shifts of Reference Compounds Relative to tetramethylsilane. Compound

␦, ppm

Solvent(s)

Sodium acetate 1,2-Dibromoethane 1,1,2,2-Tetrachloroethane 1,4-Benzoquinone 1,4-Dichlorobenzene 1,3,5-Trinitrobenzene

1.90 3.63 5.95 6.78 7.23 9.21 9.55

D2O CDCl 3 CDCl 3 ; CCl 4 CDCl 3 ; CCl 4 CCl 4 DMSO-d6* CHCl 3

* DMSO, dimethyl sulfoxide.

TABLE 7.48 Solvent Positions of Residual Protons in Incompletely Deuterated Solvents Relative to tetramethylsilane. Solvent Acetic-d3 acid-d1 Acetone-d6 Acetonitrile-d3 Benzene-d6 tert-Butanol-d1 (CH 3 )3COD Chloroform-d1 Cyclohexane-d12 Deuterium oxide Dimethyl-d6-formamide-d1 Dimethyl-d6 sulfoxide 1,4-Dioxane-d8 Hexamethyl-d18-phosphoramide Methanol-d4 Dichloromethane-d2

Group

␦, ppm

Methyl Hydroxyl Methyl Methyl Methine Methyl Methine Methylene Hydroxyl Methyl Formyl Methyl Absorbed water Methylene Methyl Methyl Hydroxyl Methylene

2.05 11.5* 2.057 1.95 6.78 1.28 7.25 1.40 4.7* 2.75; 2.95 8.05 2.51 3.3* 3.55 2.60 3.35 4.8* 5.35

* These values may vary greatly, depending upon the solute and its concentration.

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TABLE 7.48 Solvent Positions of Residual Protons in Incompletely Deuterated Solvents (Continued) Solvent

Group

Pyridine-d5

C-2 Methine C-3 Methine C-4 Methine Methyl Methine Hydroxyl

Toluene-d8 Trifluoroacetic acid-d1

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␦, ppm 8.5 7.0 7.35 2.3 7.2 11.3*

* These values may vary greatly, depending upon the solute and its concentration.

TABLE 7.49 Carbon-13 Chemical Shifts Values given in ppm on the ␦ scale, relative to tetramethylsilane.

Substituent group

Primary carbon

Secondary carbon

Tertiary carbon

Quaternary carbon

Alkanes C9C C9O C9N C9S C 9 halide (I to Cl)

5– 30 45– 60 13– 45 10– 30 3– 25

25– 45 42– 71 44– 58 22– 42 3– 40

23– 58 62– 78 50– 70 55– 67 34– 58

28– 50 73– 86 60– 75 53– 62 35– 75

Substituent group Cyclopropane Cycloalkane C4 – C10 Mercaptanes Amines: R2N 9 C Aryl 9 N Sulfoxides, sulfones Alcohols R 9 OH Ethers R 9 O 9 R Nitro R 9 NO2 Alkynes: HC # CR RC # CR Acetals, ketals Thiocyanates R 9 SCN Alkenes: H 2C " R 2C " Heteroaromatics: C"N C␣ Cyanates R 9 OCN Isocyanates R 9 NCO Isothiocyanates R 9 NCS Nitriles, cyanides

␦, ppm

Substituent group

⫺5– 5 5– 25 5– 70

Aromatics: Aryl-C Aryl-P Aryl-N Aryl-O Azomethines Carbonates Ureas Anhydrides Amides Oximes Esters: Saturated ␣,␤-Unsaturated Isocyanides R 9 NC Carboxylic acids: Nonconjugated Conjugated Salts (anion) Ketones: ␣-Halo Nonconjugated ␣,␤-Unsaturated Imides Acyl chlorides R 9 CO 9 Cl

20– 70 128– 138 35– 55 45– 87 57– 87 60– 78 63– 73 72– 95 88– 112 96– 118 100– 122 110– 150 100– 152 142– 160 105– 120 115– 135 115– 142 117– 124

␦, ppm

125– 145 119– 128 128– 138 133– 152 145– 162 159– 162 150– 170 150– 175 154– 178 155– 165 158– 165 165– 176 162– 175 162– 165 165– 184 175– 195 160– 200 192– 202 202– 220 165– 180 165– 183

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TABLE 7.49 Carbon-13 Chemical Shifts (Continued) Substituent group Thioureas Aldehydes: ␣-Halo Nonconjugated Conjugated

␦, ppm 165– 185 170– 190 182– 192 192– 208

Substituent group Thioketones R 9 CS 9 R Carbonyl M(CO)n Allenes " C "

␦, ppm 190– 202 190– 218 197– 205

Saturated heterocyclic ring systems

Unsaturated cyclic systems

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TABLE 7.49 Carbon-13 Chemical Shifts (Continued)

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Unsaturated cyclic systems (continued)

Saturated alicyclic ring systems

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TABLE 7.50 Estimation of Chemical Shifts of Alkane Carbons Relative to tetramethylsilane. Positive terms indicate a downfield shift.

␦C ⫽ ⫺2.6 ⫹ 9.1n␣ ⫹ 9.4n␤ ⫺ 2.5n␥ ⫹ 0.3n␦ ⫹ 0.1n⑀

(plus any correction factors)

where n␣ is the number of carbons bonded directly to the ith carbon atom and n␤ , n␥ , n␦ , and n⑀ are the number of carbon atoms two, three, four, and five bonds removed. The constant is the chemical shift for methane. Chain branching*

Correction factor

Chain branching*

Correction factor

1⬚(3⬚) 1⬚(4⬚) 2⬚(3⬚) 3⬚(2⬚)

⫺1.1 ⫺3.4 ⫺2.5 ⫺3.7

4⬚(1⬚) 2⬚(4⬚) 3⬚(3⬚) 4⬚(2⬚)

⫺1.5 ⫺7.2 ⫺9.5 ⫺8.4

* 1⬚ signifies a CH3 9 group; 2⬚, a 9CH 2 9 group; 3⬚, a CH 9 group; and 4⬚, a group bound to a CH 9 group, and so on. Examples: For 3-methylpentane, CH 3 9CH 2 9CH(CH 3 )9CH 2 9CH 3 ,

C

group. 1⬚ (3⬚) signifies a methyl

␦C⫽2 ⫽ ⫺2.6 ⫹ 9.1(2) ⫹ 9.4(2) ⫺ 2.5 ⫺ 1(1)[2⬚(3⬚)] ⫽ 29.4 ␦C⫽3 ⫽ ⫺2.6 ⫹ 9.1(3) ⫹ 9.4(2) ⫹ (2)[3⬚(2⬚)] ⫽ 36.2

TABLE 7.51 Effect of Substituent Groups on Alkyl Chemical Shifts These increments are added to the shift value of the appropriate carbon atom as calculated from Table 7.50. Y Straight:

Y 9 CH2 9 CH2 9 CH3 a

Branched:

b

9 CH2 9 CH2 9 CH 9 CH2 9 CH2 9 g

b

␣ carbon Substituent group Y*

a

b

g

␤ carbon

Straight

Branched

Straight

Branched

␥ carbon

20.9 24.4 20.5 33 22 31 30 48.3 58 51 51 53 68 31.2 20.0

16 20 17 28 2.5

2.5 4.1 2.5

2 3 2 2

⫺2.2 ⫺1.6 ⫺2

9 CO 9 OH 9 COO⫺ (anion) 9 CO 9 OR 9 CO 9 Cl 9 CO 9 NH 2 9 CHO 9 CO 9 R 9 OH 9 OR 9 O 9 CO 9 NH 2 9 O 9 CO 9 R 9 C 9 CO 9 Ar 9F 9 Cl 9 Br * R, alkyl group; Ar, aryl group.

45

0 1 10.2 8 8 6

63 32 25

9 10.5 10.6

24 40.8 51

1 7.7 5

⫺0.5 ⫺2 ⫺2 ⫺5.8 ⫺4

5

⫺3

6 10 10

⫺4 ⫺4.6 ⫺3.1

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TABLE 7.51 Effect of Substituent Groups on Alkyl Chemical Shifts (Continued)

␣ carbon Substituent group Y* 9I 9 NH 2 9 NH3⫹ 9 NHR 9 NR2 9 NR3⫹ 9 NO2 9 CN 9 SH 9 SR 9 CH " CH 2 9 C6 H 5 9 C # CH

Straight ⫺8 29.3 26 36.9 42 31 63 4 11 20 20 23 4.5

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␤ carbon

Branched

Straight

4 24 24 31

Branched

11.3 11.3 8 8.3 6 5 4 3 12 7 6 9 5.5

57 1 11

17

12 10 6 6

4 3 11

7

␥ carbon ⫺1.0 ⫺4.6 ⫺5 ⫺3.5 ⫺3 ⫺7 ⫺3 ⫺6 ⫺3 ⫺0.5 ⫺2 ⫺3.5

* R, alkyl group; Ar, aryl group.

TABLE 7.52 Estimation of Chemical Shifts of Carbon Attached to a Double Bond The olefinic carbon chemical shift is calculated from the equation

␦C ⫽ 123.3 ⫹ 10.6n␣ ⫹ 7.2n␤ ⫺ 7.9n␣ ⫺ 1.8n␤

(plus any steric correction terms)

where n is the number of carbon atoms at the particular position, namely,

␤ ␣ ␣⬘ ␤⬘ C9C"C9C Substituents on both sides of the double bond are considered separately. Additional vinyl carbons are treated as if they were alkyl carbons. The method is applicable to alicyclic alkenes; in small rings carbons are counted twice, i.e., from both sides of the double bond where applicable. The constant in the equation is the chemical shift for ethylene. The effect of other substituent groups is tabulated below. Substituent group

␤

␣

␣⬘

␤⬘

9 OR 9 OH 9 O 9 CO 9 CH 3 9 CO 9 CH 3 9 CHO 9 CO 9 OH 9 CO 9 OR 9 CN 9F 9 Cl 9 Br 9I 9 C6 H 5

2 6 ⫺3

29

⫺39

⫺1 ⫺1 4

⫺1 0

18 15 13.6 5.2 6 ⫺15.4 24.9 3.3 ⫺7.2 ⫺37.4 12

⫺27 6 13.2 9.1 7 14.3 ⫺34.3 ⫺5.4 ⫺0.7 7.7 ⫺11

2 2

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TABLE 7.52 Estimation of Chemical Shifts of Carbon Attached to a Double Bond (Continued) Steric correction term

Substituent pair

␣,␣⬘ ␣,␣⬘ ␣,␣ ␣⬘,␣⬘ ␤,␤

trans cis gem

0 ⫺1.1 ⫺4.8 ⫹2.5 ⫹2.3

TABLE 7.53 Carbon-13 Chemical Shifts in Substituted Benzenes

␦C ⫽ 128.5 ⫹ ⌬ Substituent group

⌬C ⫺ 1

⌬ortho

⌬meta

⌬para

9 CH 3 9 CH 2CH 3 9 CH(CH 3 )2 9 C(CH 3 )3 9 CH 2O 9 CO 9 CH 3 9 C6 H 5 9 CH " CH 2 9 C # CH 9 CH 2OH 9 CO 9 OH 9 COO⫺ (anion) 9 CO 9 OCH 3 9 CO 9 CH 3 9 CHO 9 CO 9 Cl 9 CO 9 CF3 9 CO 9 C6 H 5 9 CN 9 OH 9 OCH 3 9 OC6 H 5 9 O 9 CO 9 CH 3 9 NH 2 9 N(CH 3 )2 9 N(C6 H 5 )2 9 NHC6 H 5 9 NH 9 CO 9 CH 3 9 NO2 9F 9 Cl 9 Br 9I 9 CF3 9 NCO 9 SH 9 SCH 3 9 SO2 9 NH 2 9 Si(CH 3 )3

9.3 15.6 20.2 22.4 7.7 13.1 9.5 ⫺6.1 12.3 2.1 8 2.1 9.1 8.6 4.6 ⫺5.6 9.4 ⫺15.4 26.9 31.4 29.2 23.0 18.0 22.4 19 14.6 11.1 20.0 34.8 6.2 ⫺5.5 ⫺32.2 ⫺9.0 5.7 2.3 10.2 15.3 13.4

0.8 ⫺0.4 ⫺2.5 ⫺3.1 0 ⫺1.1 ⫺2.0 3.8 ⫺1.4 1.5 1 1.1 0.1 1.3 2.4 1.8 1.7 3.6 ⫺12.7 ⫺14.0 ⫺9.4 ⫺6.4 ⫺13.3 ⫺15.7 ⫺4 ⫺10.7 ⫺9.9 ⫺4.8 ⫺12.9 0.4 3.4 9.9 ⫺2.2 ⫺3.6 1.1 ⫺1.8 ⫺2.9 4.4

⫺0.1 0 0.1 ⫺0.1 0 0.4 0.2 0.4 ⫺1.4 0 0 0.1 0 0.6 1 0.7 ⫺0.2 0.6 1.4 1.0 1.6 1.3 0.9 0.8 1 0.7 0.2 0.9 1.4 1.3 1.7 2.6 0.3 1.2 1.1 0.4 0.4 ⫺1.1

⫺2.9 ⫺2.6 ⫺2.4 ⫺2.9 0 ⫺1.2 ⫺0.5 ⫺0.2 ⫺1.4 5.1 3 4.5 4.2 5.5 6.2 6.7 3.6 3.9 ⫺7.3 ⫺7.7 ⫺5.1 ⫺2.3 ⫺9.8 ⫺11.5 ⫺6 ⫺7.7 ⫺5.6 5.8 ⫺4.5 ⫺1.9 ⫺1.6 ⫺1.4 3.2 ⫺2.8 ⫺3.1 ⫺3.6 3.3 ⫺1.1

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TABLE 7.54 Carbon-13 Chemical Shifts in Substituted Pyridines*

␦C (k) ⫽ Ck ⫹ ⌬i

Substituent group

C2 ⫽ C6 ⫽ 149.6 ⌬C ⫺ 2 or ⌬C ⫺ 6

⌬23

⌬24

⌬25

⌬26

9.1 14.0 4.3 3.5 14.9 15.3 11.3 8.0 ⫺15.8 14.4 2.3 ⫺6.7

⫺1.0 ⫺2.1 ⫺2.8 ⫺2.6 ⫺17.2 ⫺13.1 ⫺14.7 ⫺5.1 ⫺5.0 ⫺14.7 0.7 4.8

⫺0.1 0.1 0.7 1.3 0.4 2.1 2.3 5.5 ⫺1.7 5.1 3.3 3.3

⫺3.4 ⫺3.1 3.0 4.1 ⫺3.1 ⫺7.5 10.6 6.6 3.6 ⫺2.7 ⫺1.2 ⫺0.5

⫺0.1 0.2 ⫺0.2 0.7 ⫺6.8 ⫺2.2 ⫺0.9 0.4 1.9 ⫺1.7 0.6 1.4

9 CH 3 9 CH 2CH 3 9 CO 9 CH 3 9 CHO 9 OH 9 OCH 3 9 NH 2 9 NO2 9 CN 9F 9 Cl 9 Br

Substituent group 9 CH 3 9 CH 2CH 3 9 CO 9 CH 3 9 CHO 9 OH 9 NH 2 9 CN 9 Cl 9 Br 9I

Substituent group 9 CH3 9 CH 2CH 3 9 CH " CH 2 9 CO 9 CH 3 9 CHO 9 NH 2 9 CN 9 Br

⌬32

C3 ⫽ C5 ⫽ 124.2 ⌬C ⫺ 3 or ⌬C ⫺ 5

⌬34

⌬35

1.3 0.3 0.5 2.4 ⫺10.7 ⫺11.9 3.6 ⫺0.3 2.1 7.1

9.0 15.0 ⫺0.3 7.9 31.4 21.5 ⫺13.7 8.2 ⫺2.6 ⫺28.4

0.2 ⫺1.5 ⫺3.7 0 ⫺12.2 ⫺14.2 4.4 ⫺0.2 2.9 9.1

⫺0.8 ⫺0.3 ⫺2.7 0.6 1.3 0.9 0.6 0.7 1.2 2.4

⫺2.3 ⫺1.8 4.2 5.4 ⫺8.6 ⫺10.8 4.2 ⫺1.4 ⫺0.9 0.3

⌬42 ⫽ ⌬46

⌬43 ⫽ ⌬45

C4 ⫽ 136.2 ⌬C ⫺ 4

0.5 0 0.3 1.6 1.7 0.9 2.1 3.0

0.8 ⫺0.3 ⫺2.9 ⫺2.6 ⫺0.6 ⫺13.8 2.2 3.4

10.8 15.9 8.6 6.8 5.5 19.6 ⫺15.7 ⫺3.0

* May be used for disubstituted, polyheterocyclic, and polynuclear systems if deviations due to steric and mesomeric effects are allowed for.

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TABLE 7.55 Carbon-13 Chemical Shifts of Carbonyl Group

X

Y

␦C

X

Y

␦C

CH 3 9 CH 3 9 CH 3 9

9 CH " CH 2 9 C6 H 5 9 CH 2 9 CO 9 CH 3

CH 3 9 CH 3 9

9 CH 2CHO 9 C6 H 5 9 CH 3

CH 3 9 CH 3 9 CH 3 9 CH 3 9 CH 3 9 CH 3 9 CH 3 9 CH 3 9 CH 3 9 CH 3 9 CH 3 9 CH 3 9 CH 3 9

9 2,6-(CH 3 )2C6 H 5 9 OH 9 O⫺ (anion) 9 OCH 3 9 O 9 CH " CH 2 9 O 9 CH(CH 3 )2 9 O 9 CO 9 CH 3 9 NH 2 9 NHCH 3 9 N(CH 3 )2 9 Cl 9 Br 9I

196.9 197.6 201.9 (keto) 191.4 (enol) 167.7 196 (m, p) 199 (o) 206 178 181.5 170.7 167.7 170.3 167.3 172.7 172 169.5 169.6 165.6 158.9

H9 H9 H9

9 CH 3 9 CCl 3 9 NH 2

199.7 175.3 165.5

H9

9 N(CH 3 )2

162.4

H9 H9 H9 (CH 3 )2CH 9 C6H 5 9 CF3 9 CCl 3 9 CH 3CH(NH 2 ) 9 CF3 9 H2N 9 2-Furyl (CH 3 )2 N 9 CH 2 " CHCH 2O 9 CO 9 CH 3CH 2 9 CH 3 9 CH 2 9 CH 3 9 CH 3 9

2-Furyl 2-Pyrrolyl 2-Thienyl 9 OH 9 OH 9 OH 9 OH 9 OH 9 OCH 2CH 3 9 OCH 2CH 3 9 OCH 3 9 C6 H 5 9 OCH 2CH " CH 2 9 CH 2CH 3 9 O 9 CO 9 CH 2CH 3 9 CH 3 9 CH 2CH 3

153.3 134.0 143.3 184.8 172.6 163.0 168.0 176.5 158.1 157.8 159.1 170.8 157.6 211.4 170.3 205.8 207

n

␦C

3 4 5 6 7

207.9 218.2 211.3 211.4 216.0

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TABLE 7.56 One-Bond Carbon-Hydrogen Spin Coupling Constants Structure

JCH , Hz

Structure

JCH , Hz

H 9 CH 3 H 9 CH 2CH 3 CH 3 9 CH 2 9 CH 3 H 9 C(CH 3 )2 H 9 CH 2CH 2OH H 9 CH 2CH " CH 2 H 9 CH 2C6 H 5 H 9 CH 2C # CH H 9 CH 2CN H 9 CH(CN)2 H 9 CH 2 9 halogen H 9 CHF2 H 9 CHCl 2 H 9 CH 2NH 2 H 9 CH 2NH 3⫹ H 9 CH 2OH (or H 9 CH 2OR) H 9 CH(OR)2 H 9 C(OR)3 H 9 C(OH)R 2 H 9 CH 2NO2 H 9 CH(NO2 )2 H 9 CH 2COOH H 9 CH(COOH)2 H 9 CH " CH 2 H 9 C(CH 3 ) " C(CH 3 )2 H 9 CH " C(tert-C4 H 9 )2 H 9 C(tert-C4 H 9 ) " C(tert-C4 H 9 )2 Methylenecycloalkane C4 – C7 H 9 CH " C " CH 2 H 9 C(C6 H 5 ) " CH(C6 H 5 ) cis trans Cyclopropene Ht Hg gem C"C cis Hc F trans

125.0 124.9 119.2 114.2 126.9 122.4 129.4 132.0 136.1 145.2 149– 152 184.5 178.0 133.0 145.0 140– 141 161– 162 186 143 146.0 169.4 130.0 132.0 156.2 148.4 152 143

H 9 CH " O; CH 3 9 CH " O H 2N 9 CH " O (CH 3 )2N 9 CH " O H 9 COOH H 9 COO⫺ (anion) H 9 CO 9 OCH 3 H 9 CO 9 F CH 3CH2 9 O 9 CHO Cl 3 9 CHO H 9 C # CH H 9 C # CCH 3 H 9 C # CC6 H 5 H 9 C # CCH 2OH H 9 CN Cyclopropane Cyclobutane Cyclopentane Cyclohexane Tetrahydrofuran 2,5 3,4 1,4-Dioxane Benzene Fluorobenzene 2,6 3,5 4 Bromobenzene 2,6 3,5 4 Benzonitrile 2,6 3,6 4 Nitrobenzene 2,6 3,5 4 Mesitylene 2,6 3,5 4 N

172 188.3 191 222 195 226 267 225.6 207 249 248 251 241 269 161 136 131 123 149 133 145 159 155 163 161 171 164 161 173 166 163 171 167 163 154 170 163 152

2,4,6-Trimethylpyridine

158

Ht

153– 155 168 155 151 220 200 159 162

Hc

Hg gem cis Cl trans

195 163 161

Ht

Hg

162 157 162

N H

Hc

gem cis C"C CHO trans

Ht

Hg

177 163 165

O

163 177

S

C"C

C"C Hc

CN

H C"N CH3

gem cis trans

OH cis trans

N N H

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2,5 3,4

183 170

2,5 3,4

201 175

2,5 3,4

185 167

3,5 4

190 178

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TABLE 7.56 One-Bond Carbon-Hydrogen Spin Coupling Constants (Continued) Structure

JCH , Hz

N

Structure N

2 4

N H

208 199

JCH , Hz

N N

216

N H

N N

205

N H

TABLE 7.57 Two-Bond Carbon-Hydrogen Spin Coupling Constants Structure

2

JCH , Hz ⫺4.5 5.9 ⫺3.4 1.2 26.7 ⫺2.4 5.5 26.9 26.9 6.0 20.0 1.0

CH 3 9 CH 2 9 H CCl 3 9 CH 2 9 H ClCH 2 9 CH 2Cl Cl 2CH 9 CHCl 2 CH 3 9 CHO CH 2 " CH 2 (CH3 )2C " O CH 2 " CH 9 CH " O (C2 H 5 )CH 9 CHO H 2 NCH " CH 9 CHO H 2 NCH 9 CH 9 CHO C6 H 6

2

Structure

JCH , Hz

n⫽4 (CH2)n C " CH2 n ⫽ 5 n⫽6 H H cis C"C trans Cl Cl HC # CH C6H 5O 9 C # CH HC # C 9 CHO ClCH 2 9 CHO Cl 2CH 9 CHO Cl 3C 9 CHO C6 H 5 9 C # C # CH 3

4.2 5.2 5.5 16.0 0.8 49.3 61.0 33.2 32.5 35.3 46.3 10.8

TABLE 7.58 Carbon-Carbon Spin Coupling Constants Structure* H3C 9 CH 3 H 3C 9 CHR 2 H 3C 9 CH 2Ar H 3C 9 CH 2CN H 3C 9 CH 2 9 CH 2OH C-1, C-2 C-2, C-3 H 3C 9 CH 2NH 2 C9C"O C9C9C"O C 9 C 9 Ar C 9 CO 9 O⫺ (anion) C 9 CO 9 N C 9 CO 9 OH * R, alkyl group; Ar, aryl group.

JCC , Hz

Structure

JCC , Hz

35 37 34 33

C 9 CO 9 OR C 9 CN C 9 C # C 2JCC ⫽ 11.8 H 2C " CH 2 C " C 9 CO 9 OH C " C 9 CN C " C 9 Ar C6 H 6 C3 H 5 NO2 1-2 2-3, 3-4 3 J2-5

59 52– 57 67 68 70– 71 71 67– 70

38 34 37 38– 40 36 43 52 52 57

57 55 56 7.6

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TABLE 7.58 Carbon-Carbon Spin Coupling Constants (Continued) Structure* C6H 5 I 1-2 2-3 3-4 3J 2-5 C6H 5 9 OCH 3 2-3 3-4 C6H 5NH 2 1-2 2-3 3-4 3 J2-5 C6 H 5CH 3

JCC , Hz

60 53 58 8.6 58 56 61 58 57 7.9 44

Structure Pyridine 2-3 3-4 3J 2-5 Furan Pyrrole Thiophene H 2C " C " C(CH 3 )2 9C#C9 Structure CH 3 9 CO " CH 3 CH 3 9 C # CH CH 3CH 2 9 CN

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JCC , Hz

54 56 14 69 69 64 100 170– 176 2

JCC , Hz 16 11.8 33

* R, alkyl group; Ar, aryl group.

TABLE 7.59 Carbon-Fluorine Spin Coupling Constants Structure* F

H ⫺158

C H

H

F

H ⫺235

C F

H

F

F C

F

H

F

F C

F

F

F

F

Structure* p-F 9 C6 H 4 9 CF3 p-F 9 C6 H 4 9 CO 9 CH 3 p-F 9 C6 H 4 9 NO2 F 9 C6 H 5 2 JCF ⫽ 21.0 3 JCF ⫽ 7.7 4 JCF ⫽ 3.4 F

⫺274

C " CH2

F

CH3

F

H C

F ⫺259

* Ar, aryl group; R, alkyl group.

⫺252 ⫺253 ⫺257 ⫺244

⫺287

C"O

⫺308

C"O

⫺353

C"O

⫺369

F F R F ⫺165 H

Ar

F 9 CH 2CH 2 9 or F 9 CR 3 p-F 9 C6 H 4 9 OR p-F 9 C6 H 4 9 R

JCF , Hz

F

⫺271

C

H

JCF , Hz

⫺167 ⫺237 ⫺241

F

H ⫺241

C F

CH2OH

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TABLE 7.59 Carbon-Fluorine Spin Coupling Constants (Continued) Structure* F

JCF , Hz

Structure*

F

F ⫺278

C F F

F ⫺289

C

CH2OH F

F

CO 9 CH3

⫺265

C F

JCF , Hz

OCF3 * Ar, aryl group; R, alkyl group.

TABLE 7.60 Carbon-13 Chemical Shifts of Deuterated Solvents Relative to tetramethylsilane. Solvent Acetic-d3 acid-d1 Acetone-d6 Acetonitrile-d3 Benzene-d6 Carbon disulfide Carbon tetrachloride Chloroform-d1 Cyclohexane-d12 Dimethyl sulfoxide-d6 1,4-Dioxane-d6 Formic-d1 acid-d1 Methanol-d4 Methylene chloride-d2 Nitromethane-d3 Pyridine-d5

Group

␦, ppm

Methyl Carbonyl Methyl Carbonyl Methyl Carbonyl

20.0 205.8 28.1 178.4 1.3 117.7 128.5 193 97 77 25.2 39.5 67 165.5 47– 49 53.8 57.3 123.5 135.5 149.9

Carbonyl

C3 , C5 C4 C2 , C6

TABLE 7.61 Carbon-13 Spin Coupling Constants with Various Nuclei Nuclei 2

H

Structure CDCl3 CD3 9 CO 9 CD3 (CD3 )2 SO C6 D6

1

J, Hz 32 20 22 26

2

J, Hz

3

J, Hz

4

J, Hz

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TABLE 7.61 Carbon-13 Spin Coupling Constants with Various Nuclei (Continued) Nuclei 7

Li

CH3 Li

15

(C6 H5 )4 B⫺

49

N

(CH3 )4 N⫹ CH3 NC

10 8

Si

(CH3 ) 4Si

52

14

29

31

P

(CH3 )3 P (C4 H9 )3 P (C6 H5 )3 P (CH3 )4 P ⫹ (C4 H9 )4 P ⫹ (C6 H5 )4 P ⫹ R(RO)2 P " O (C4 H9 O)3 P " O

Se

2

J, Hz

B

11

77

1

Structure

J, Hz

4

J, Hz

3

14 11 12 56 48 88 142

(CH3 )2 Se (CH3 )3 Se ⫹

3

J, Hz

12 20

5 7

0

4 11 5– 7 6

15 13

3

37

47

11

7

62 50

113

Cd

(CH3 )2 Cd

119

Sn

(CH3 )4 Sn (CH3 )3 SnC6 H5

340 474

125

Te

(CH3 )2Te

162

Hg

(CH3 )2 Hg (C6 H5 )2 Hg

687 1186

88

102

18

(CH3 )2 Pb (C6 H5 )4 Pb

250 481

68

81

20

199

207

Pb

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513, 537

TABLE 7.62 Boron-11 Chemical Shifts Values given in ppm on the
scale, relative to B(OCH3 )3. Structure R3 B Ar3 B BF3 BCl3 BBr3 BI3 B(OH)3 B(OR)3 B(NR 2 )3 C6 H5 BCl2 C6 H5 B(OH)2 C6 H5 B(OR)2 M(BH4 ) B(BF4 )


, ppm ⫺67 to ⫺68 ⫺43 24 ⫺12 ⫺6 41 36 0– 1 ⫺13 ⫺36 ⫺14 ⫺10 55– 61 19– 20

Structure


, ppm

NH 9 BH HB

NH

⫺12

NH 9 BH H

H B

37 H

N R2

H H

H

NR2 B

H

H B

B NR2

15

H

(CH3 )2N 9 B(CH3 )2

62

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TABLE 7.62 Boron-11 Chemical Shifts (Continued) Structure


, ppm

Addition complexes R2 O · BH3 R3 N · BH3 R2 NH · BH3

18– 19 25 33

N BH3 R2 O(or ROH) · BF3 R2 O(or ROH) · BCl3 R2 O(or ROH) · BBr3 R2 O(or ROH) · BI3 N BBr3

Structure


, ppm

Boranes B2 H6 B4 H10 (BH2 ) (BH)

1 25 60

31 Base 17– 19 ⫺7 to ⫺8 23– 24 74– 82

B5 H9 B5 H11 B10 H14

Apex

31 ⫺16 7

70 50 54

24

TABLE 7.63 Nitrogen-15 (or Nitrogen-14) Chemical Shifts Values given in ppm on the
scale, relative to NH3 liquid. Substituent group Aliphatic amines Primary Secondary Tertiary Cyclo, primary Aryl amines Aryl hydrazines Piperidines, decahydroquinolines Amine cations Primary Secondary Tertiary Quaternary Enamines, tertiary type Alkyl Cycloalkyl Aminophosphines Amine N-oxides Ureas Aliphatic Aryl Sulfonamides Amides HCO 9 NHR R ⫽ primary R ⫽ secondary R ⫽ tertiary


, ppm

1– 59 7– 81 14– 44 29– 44 40– 100 40– 100 30– 82

19– 59 40– 74 30– 67 43– 70 29– 82 55– 104 59– 100 95– 122 63– 84 105– 108 79– 164

100– 115 104– 148 96– 133

Substituent group Amides (continued) HCO 9 NH 9 Aryl RCO 9 NHR or RCO 9 NR2 RCO 9 NH 9 Aryl Aryl 9 CO 9 H 9 Aryl Guanidines Amino Imino Thioureas Thioamides Cyanamides R2 N 9 9 CN Carbodiimides Isocyanates Alkyl, primary Alkyl, secondary and tertiary Aryl Isothiocyanates Azides

Lactams Hydrazones Amino Imino Cyanates Nitrile N-oxides, fulminates


, ppm

138– 141 103– 130 131– 136 ca 126 30– 60 166– 207 85– 111 135– 154 ⫺12 to ⫺38 175– 200 95– 120 14– 32 54– 57 ca 46 90– 107 52– 80 108– 122 240– 260 113– 122 141– 167 319– 327 155– 182 195– 225

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TABLE 7.63 Nitrogen-15 (or Nitrogen-14) Chemical Shifts (Continued) Substituent group Isonitriles Alkyl, primary Alkyl, secondary Aryl Nitriles Alkyl Aryl Thiocyanates Diazonium Internal Terminal Diazo Internal Terminal Nitrilium ions Azinium ions Azine N-oxides Nitrones Imides Imines


, ppm

162– 178 191– 199 ca 180 235– 241 258– 268 265– 280 222– 230 315– 322 226– 303 315– 440 123– 150 185– 220 230– 300 270– 285 170– 178 310– 359

Substituent group Oximes Nitramines Amine 9 NO2 Nitrates gem-Polynitroalkanes Nitro Aryl Alkyl Hetero, unsaturated Azoxy Azo Nitrosamines Nitrites Thionitrites Nitroso Aliphatic amines, NO Aryl

top of rh base of rh


, ppm 340– 380 252– 280 328– 355 310– 353 310– 353 350– 382 372– 410 354– 367 330– 356 504– 570 222– 250 525– 550 555– 582 720– 790 535– 560 804– 913

Saturated cyclic systems

n n n n

⫽2 ⫽3 ⫽4 ⫽5

7.5 (in C6H6) 18.0 (in H2O)

⫺8.5 25.3 36.7 37.7

32.1

cis trans

42.4 52.9

35.5

Unsaturated cyclic systems

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TABLE 7.63 Nitrogen-15 (or Nitrogen-14) Chemical Shifts (Continued) Unsaturated cyclic systems (continued)

X


, ppm

O S Se

517 331 373

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TABLE 7.64 Nitrogen-15 Chemical Shifts in Monosubstituted Pyridine


⫽ 317.3 ⫹ i Substituent

 C-2

9 CH3 9 CH2 CH3 9 CH(CH3 )2 9 C(CH3 )3 9 CN 9 CHO 9 CO 9 CH3 9 CO 9 OCH2 CH3 9 OCH3 9 OH 9 NO2 9 NH2 9F 9 Cl 9 Br

⫺0.4 ⫺1.8 ⫺5.1 ⫺2.5 ⫺0.9 10 ⫺9 11.8 ⫺49 ⫺126 ⫺23 ⫺45 ⫺42 ⫺4 2

 C-3 0.3

⫺0.8 11 15 0 ⫺2 1 10 ⫺18 4 8

 C-4 ⫺8.0 ⫺6.6 ⫺5.9 ⫺5.8 10.6 29 11 ⫺5 ⫺23 ⫺118 22 ⫺46 ⫺6 7

TABLE 7.65 Nitrogen-15 Chemical Shifts for Standards Values given in ppm, relative to NH3 liquid at 23⬚C.


, ppm

Substance Nitromethane (neat)

380.2

Potassium (or sodium) nitrate (saturated aqueous solution) C(NO2 )4 (CH3 )2 9 CHO (neat) (C2 H5 )4 N⫹Cl⫺ (CH3 )4 N⫹Cl⫺ NH4Cl NH4 NO3 NH3

376.5 331 103.8 64.4 43.5 27.3 20.7 0.0 ⫺15.9

Conditions For organic solvents and acidic aqueous solutions For neutral and basic aqueous solutions For nitro compounds For organic solvents and aqueous solutions Saturated aqueous solution Saturated aqueous solution Saturated aqueous solution Saturated aqueous solution Liquid, 25⬚C Vapor, 5 atm

TABLE 7.66 Nitrogen-15 to Hydrogen-1 Spin Coupling Constants Structure

J, Hz

R 9 NH2 and R2 NH Aryl 9 NH2 p-CH3O 9 aryl 9 NH2 p-O2N 9 aryl 9 NH2 Amine salts (alkyl and aryl) Aryl 9 NHOH Aryl 9 NHCH3 Aryl 9 NHCH2F

61– 67 78 79 90– 93 73– 76 79 87 90

Structure Aryl 9 NHNH2 p-O2N 9 aryl 9 NHNH2 Aryl 9 SO2 9 NH2 Aryl 9 SO2 9 NHR O Hsyn (to 9 CO 9) C9N H Hanti

J, Hz 90 99 81 86 88 92– 93

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TABLE 7.66 Nitrogen-15 to Hydrogen-1 Spin Coupling Constants (Continued) Structure O

J, Hz

H C9N

88– 92

R R Pyrrole HC # NH⫹ P 9 NH2

97 133– 136 82– 90

Structure (R3 Si)2NH CF3 9 S 9 NH2 (CF3 9 S)2NH Pyridinium ion Quinolinium ion

J, Hz 67 81 99 90 96

TABLE 7.67 Nitrogen-15 to Carbon-13 Spin Coupling Constants Structure

J, Hz

Alkyl amines Cyclic alkyl amines Alkyl amines protonated Aryl amines Aryl amines protonated CH3CO 9 NH2 H2N 9 CO 9 NH2 Aryl 9 NO2

4– 4.5 2– 2.5 4– 5 10– 14 9 14– 15 20 15

Structure Alkyl 9 NO2 R 9 CN⫹ ⫺ CH3 9 N # C H3C 9 N 9N#C Diaryl azoxy anti syn

J, Hz 11 18 10 9 18 13

TABLE 7.68 Nitrogen-15 to Fluorine-19 Spin Coupling Constants Structure

J, Hz

NF3 F4N2 FNO2 F3NO F3C 9 O 9 NF2 FCO 9 NF2 (NF4)⫹SbF6⫺ (NF4)⫹AsF6⫺ (N2F)⫹AsF6⫺ F3C 9 NO2 F N"N (2J  10) F

155 164 158 190 164– 176 221 323 328 459 215

F

F N"N

(2J  52)

190

203

Structure Pyridine 2-F 3-F 2,6-di-F Pyridinium ion 2-F 3-F Quinoline, 8-F Aniline 2-F 3-F 4-F Anilinium ion 2-F 3-F 4-F

J, Hz

52 4 37 23 3 3 0 0 1.5 1.4 0.2 0

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TABLE 7.69 Fluorine-19 Chemical Shifts Values given in ppm on the
scale, relative to CCl3 F. Substituent group 9 SO2 9 F 9 CO 9 F N 9 CO 9 F Aryl 9 CF2Cl 9 CF2I 9 CF2Br R 9 CF2Cl C 9 CF3 and aryl 9 CF3 9 CS 9 CF3 CF 9 CF3 9 S 9 CF3 9 S 9 CF2 9 S 9 P 9 CF3 N 9 CF3 N 9 CF2 9 C 9 O 9 CF2 9 R 9 O 9 CF2 9 CF3 9 CH2 9 CF3 HO 9 CO 9 CF3 9 CHF 9 CF3 9 CF2 9 CF3 9 CS 9 F CF3 9 C 9 N 9 CO 9 CF2 9 CF3 9 CF2 9 9 CF2Br 9 C 9 CF2 9 S 9 9 CF " 9 CF2 9 CF3 9 CO 9 CF2 9 9 C(halide) 9 CF2 9 9 CF2 9 CF3 9 CF2 9 CF2 9 9 CF2 9 CH2 9 9 CF2 9 CHF2 9 CF2H F2


, ppm ⫺67 to ⫺42 (aryl)(alkyl) ⫺29 to ⫺20 ⫺5 49 56 63 61– 71 56– 73 70 71– 73 41 39 46– 66 40– 58 85– 127 70– 91 70– 91 76– 77 77 81 78– 88 81 84– 96 83 86– 126 91 91– 98 180– 192 111 116– 131 119– 128 121– 125 121– 129 122– 133 128– 132 136– 143 151– 156

F2

147

F2

96– 133

F

159

Substituent group Cyclohexane-F

Perfluorocycloalkane CF 9 CF3 CF(CF3)2 9 CFH 9 9 CFH2 F2C " CF2 Fc CF2 9 CF2H C"C Fg Ft cis trans gem F2 F3 C"C H H C"C F1 F-1 F-2 F-3 ClFC " CH 9 CF3 Cycloalkenes " CF 9 CF2 9 C(CF3 or H) 9 9 CF2 9 CF2 9 C(CF3 or CH3 ) " 9 CF2 9 CF2 9 CH " 9 CF2 9 CF2 9 CF " Aryl 9 F C10 H7 9 F F-1 F-2 C6 H5 9 C6 H4 9 F F-2 F-3 F-4 C6 F6


, ppm 210 (axial) to 240 (equatorial) 131– 138 163– 198 180– 191 198– 231 235– 244 133

108 92 192

H

126 155 162 61

101– 113 110– 114 113– 116 119– 122 113 127 114 117 113 109 163

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TABLE 7.70 Fluorine-19 Chemical Shifts for Standards Substance

Formula


, ppm

Trichlorofluoromethane ,,-Trifluorotoluene Trifluoroacetic acid Carbon tetrafluoride Fluorobenzene Perfluorocyclobutane

CFCl3 C6 H5CF3 CF3COOH CF4 C6 H5 F C4F8

0.0 63.8 76.5 76.7 113.1 138.0

TABLE 7.71 Fluorine-19 to Fluorine-19 Spin Coupling Constants Structure F2C

JFF , Hz

cycloalkane

gem Unsaturated compounds C"C gem trans cis Aromatic compounds, monocyclic ortho meta para Alkanes CFCl2 9 CF2 9 CFCl2 CFCl2 9 CF2 9 CCl3 CF2Cl 9 CF2 9 CF2Cl CF3 9 CF2 9 CF2Cl (or 9 CF3 ) CF3 9 CF2 9 CF2Cl CF3 9 CF2 9 CF2Cl CF3 9 CF2 9 CF3

212– 260 30– 90 115– 130 9– 58 18– 22 0– 7 12– 15 6 5 1 ⬍1 2 9 7

TABLE 7.72 Silicon-29 Chemical Shifts Values given in ppm on the
scale relative to tetramethylsilane. n Substituent group X in (CH3 )4 – n SiXn 9F 9 Cl 9 Br 9I 9H 9 C2 H5 9 C6 H5 9 CH " CH2 9 Oalkyl 9 Oaryl 9 O 9 CO 9 alkyl 9 N(CH3 )2

1

2

3

4

35 30 26 9 ⫺19 2 ⫺5 ⫺7 14– 17 17 22 6

9 32 20 ⫺34 ⫺42 5 ⫺9 ⫺14 ⫺3 to ⫺6 ⫺6 4 ⫺2

⫺52 13 ⫺18 ⫺18 ⫺65 7 ⫺12 ⫺21 ⫺41 to ⫺45 ⫺54 ⫺43 ⫺18

⫺109 ⫺19 ⫺94 ⫺346 ⫺93 8 ⫺23 ⫺79 to ⫺83 ⫺101 ⫺75 ⫺28

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TABLE 7.72 Silicon-29 Chemical Shifts (Continued)


, ppm

Structure Hydrides H3 Si 9 9 H2Si 9 HSi Silicates Orthosilicate anions Silicon in end position Silicon in middle Branching silicons Cross-linked silicons Methyl siloxanes (CH3)2Si 9 O 9 (end position) O9 (CH3)2Si (middle) O9 O9 CH3Si(H) (middle) O9

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, ppm

Structure O9

⫺39 to ⫺60 ⫺5 to ⫺37 ⫺2 to ⫺39 ⫺69 to ⫺72 ⫺77 to ⫺81 ⫺85 to ⫺89 ⫺93 to ⫺97 ⫺107 to ⫺120 6– 8 ⫺18 to ⫺23

CH3Si 9 O 9

(branching)

⫺65 to ⫺66

O9 O9 9 O 9 Si 9 O 9

(cross-linked)

O9 Polysilanes F3Si 9 SiF3 Cl3Si 9 SiCl3 (CH3O)3Si 9 Si(OCH3)3 (CH3)3Si 9 Si(CH3)3 (CH3)2Si[Si(CH3)3]2 HSi[Si(CH3)3]3 Si[Si(CH3)3]4

⫺105 to ⫺110

⫺74 ⫺8 ⫺53 ⫺20 ⫺48 ⫺117 ⫺135

⫺35 to ⫺36

TABLE 7.73 Phosphorus-31 Chemical Shifts Values given in ppm on the
scale, relative to 85% H3PO4 .

Structure P4 PR3 PHR2 PH2R PH3 PF3 PRF2 PCl3 PRCl2 PR2Cl PBr3 PRBr2 PR2Br PI3 P(CN)3 P(SiR3 )3 P(OR)3 P(OR)2Cl P(OR)Cl2 P(SR)3 P(SR)2Cl P(SR)Cl2 P(SR)2Br

Identical atoms attached directly to phosphorus

Non-identically substituted phosphorus R ⫽ CH3

R ⫽ C2 H5

R ⫽ C6 H5

461 62 99 164

20 56 128

6 41 122

⫺168

⫺207

⫺192 ⫺94

⫺196 ⫺119

⫺162 ⫺81

⫺184 ⫺91

⫺194 ⫺116

⫺152 ⫺71

251 ⫺141 ⫺169 ⫺114 ⫺125 ⫺188 ⫺206

⫺139 ⫺165 ⫺177 ⫺115 ⫺186 ⫺211

⫺127 ⫺157 ⫺173 ⫺132 ⫺183 ⫺204 ⫺184

241 ⫺97 ⫺220 ⫺227 ⫺178 136

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TABLE 7.73 Phosphorus-31 Chemical Shifts (Continued)

Structure P(SR)Br2 P(NR2 )3 P(NR2 )Cl2 PR(NR2 )2 PR2(NR2 ) F2P 9 PF2 Cl2P 9 PCl2 I2P 9 PI2 PH2⫺K⫹ P(CF3 )3 P4O6

Structure P(NCO)3 P(NCO)2 X P(NCO)X2 P(NCS)3 P(NCS)2 X P(NCS)X2

Structure O " PR3 O " PHR2 O " PF3 O " PRF2 O " PCl3 O " PRCl2 O " PR2Cl O " P(OR)3 O " P(OR)2Cl O " P(OR)Cl2 O " PH(OR)2 O " PR2 (OC2 H5 ) O " PR(OC2 H5 )2 O " P(NR2 )3 O " PR2 (NR 2 ) O " P(OR)2NH2 O " P(OR)2(NCS) O " P(SR)3 O " PBr3 O " P(NCO)3 O " P(NCS)3 O " P(NH2 )3

Identical atoms attached directly to phosphorus

⫺226 ⫺155 ⫺170 255 3 ⫺113 Identical atoms attached directly to phosphorus ⫺97 ⫺86

Identical atoms attached directly to phosphorus

Non-identically substituted phosphorus R ⫽ CH3

R ⫽ C2 H5

R ⫽ C6 H5

⫺204 ⫺123 ⫺166 ⫺86 ⫺39

⫺118 ⫺162 ⫺100 ⫺62

⫺151 ⫺100

Non-identically substituted phosphorus X⫽F

X ⫽ Cl

X ⫽ Br

⫺128 ⫺131

⫺128 ⫺166

⫺127

⫺114 ⫺155

⫺112 ⫺153

Non-identically substituted phosphorus R ⫽ CH3

R ⫽ C2 H5

R ⫽ C6 H5

⫺36 ⫺63

⫺48

⫺25 ⫺23

⫺27

⫺29

⫺11

⫺45 ⫺65 ⫺1 ⫺6 ⫺6 ⫺19 ⫺50 ⫺30 ⫺23 ⫺44 ⫺15

⫺53 ⫺77 1 ⫺3 ⫺6 ⫺15 ⫺52 ⫺33 ⫺24

⫺34 ⫺43 18 6 ⫺2

36 ⫺2

⫺66 103 41 62 ⫺22

⫺12 19 ⫺61

⫺31 ⫺17 ⫺2 ⫺26 ⫺3 29 ⫺55

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TABLE 7.73 Phosphorus-31 Chemical Shifts (Continued)

Structure PF5 PF6⫺H⫹ PBr5 P(OC2 H5 )5 PO43⫺ O " P[OSi(CH3 )3]3 H4P2O7 Phosphonates Phosphonium cations Alkyl Aryl (O3P 9 PO3 )4⫺ Polyphosphates O"P9O9 (OR)2 (end group)

Structure S " PR3 S " PCl3 S " PRCl2 S " PR2Cl S " PBr3 S " PRBr2 S " PR2Br S " P(OR)3 S " P(OR)Cl2 S " P(OR)2Cl S " PH(OR)2 S " P(SR)3 S " P(NH2 )3 S " P(NR2 )3 Se " P(OR)3 Se " P(SR)3 P(OR)5 PRF4 PR2 F3

Identical atoms attached directly to phosphorus 35 144 101 71 ⫺6 33 11 ⫺24 to ⫺2

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Identical atoms attached directly to phosphorus

Structure O 9O9P9O9 OR (middle group) O

ca 18

9O9P9O9 O

⫺43 to ⫺32 ⫺35 to ⫺18 ⫺9

P (etc.) (branch group)

ca 30

ca 6 Identical atoms attached directly to phosphorus

⫺29

Non-identically substituted phosphorus R ⫽ CH3

R ⫽ C2 H5

R ⫽ C6 H5

⫺59

⫺55

⫺43

⫺80 ⫺87

⫺94 ⫺109

⫺75 ⫺80

⫺21 ⫺64 ⫺73 ⫺59 ⫺73 ⫺74 ⫺98

⫺42 ⫺98 ⫺68 ⫺56 ⫺68 ⫺69 ⫺92

⫺20

⫺82 ⫺78 ⫺82

⫺78 ⫺71 ⫺76 71 30 ⫺6

112

⫺60

30 ⫺9

⫺53 ⫺54 ⫺59 ⫺59 ⫺92 ⫺58 86 42

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TABLE 7.74 Phosphorus-31 Spin Coupling Constants Substituent group PH 9 PH2⫺ RPH2 P 9 CH3 P 9 CH2 9 Ha Hb C"C P Hg

␣ ␤ ␥ (Halogen)2P 9 CH P 9 NH P 9 O 9 CH3 P 9 O 9 CH2 9 R P 9 O 9 CHR2 P 9 SCH P 9 N 9 CH P 9 C 9 CH

JPH , Hz 180– 225 134 160– 210 1– 6 14

Substituent group P9F

JPP , Hz 1320– 1420 (1F) (3F) 1140– 1290 1020– 1110 920– 985 (alkyl) (aryl)

RPF2 R2PF RP(N)F 9O PF

1225– 1305

9O 12– 22 30– 40 14– 20 16– 20 10– 28 11– 15 6– 10 3– 7 5– 20 8– 25 0– 4

1310

(OCN)PF N9P

1100– 1200 F

P 9 CF P

60– 90 F

ortho meta para

0– 60 1– 7 0– 3

P ortho meta O " PHR2 O 9 PH(S)R O2 PHR O2PH(N) O2PH(S or Se) O3PH

7– 10 2– 4 210– 500 490– 540 500– 575 560– 630 630– 655 630– 760

S(or Se) " P 9 H

490– 650

S(or Se) " PHR2

420– 454

O " P 9 CH3

7– 15

O " P 9 CH " C

15– 30

O " P 9 CH 9 Aryl(or C " O)

15– 30

(Halogen)2P 9 N 9 CH S " P 9 CH P 9 CH⫹3 P 9 H⫹

9– 18 11– 15 12– 17 490– 600

Substituent group 9P F

axial equatorial

JPF , Hz 600– 860 800– 1000

O " P 9 CF

110– 113

O"P9F

980– 1190

P9O9P9F Substituent group

H 3B 9 P 9 N

Substituent group P9P

2 JPB , Hz

80

JPP , Hz 220– 400

O"P9P"O

330– 500

S"P9P"S

15– 500

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TABLE 7.74 Phosphorus-31 Spin Coupling Constants (Continued) Substituent group

JPP , Hz

P9C9P P9O9P

20– 40

P9S9P

86– 90

O"P9O9P"O

7.8 7.8.1

Substituent group

ca 70

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JPP , Hz

O"P9N9P"O H P9N

8– 30

N

5– 66

P P9N P"N9P"N9

15– 25

5– 65

MASS SPECTROMETRY Correlation of Mass Spectra with Molecular Structure

7.8.1.1 Molecular Identification. In the identification of a compound, the most important information is the molecular weight. The mass spectrometer is able to provide this information, often to four decimal places. One assumes that no ions heavier than the molecular ion form when using electron-impact ionization. The chemical ionization spectrum will often show a cluster around the nominal molecular weight. Several relationships aid in deducing the empirical formula of the parent ion (and also molecular fragments). From the empirical formula hypothetical molecular structures can be proposed, using the entries in the formula indices of Beilstein and Chemical Abstracts. 7.8.1.2 Natural Isotopic Abundances. The relative abundances of natural isotopes produce peaks one or more mass units larger than the parent ion (Table 7.75a). For a compound CwHxOzNy , a formula allows one to calculate the percent of the heavy isotope contributions from a monoisotopic peak, PM , to the PM ⫹ 1 peak: 100

PM ⫹ 1 ⫽ 0.015x ⫹ 1.11w ⫹ 0.37y ⫹ 0.037z PM

Tables of abundance factors have been calculated for all combinations of C, H, N, and O up to mass 500 (J. H. Beynon and A. E. Williams, Mass and Abundance Tables for Use in Mass Spectrometry, Elsevier, Amsterdam, 1963). Compounds that contain chlorine, bromine, sulfur, or silicon are usually apparent from prominent peaks at masses 2, 4, 6, and so on, units larger than the nominal mass of the parent or fragment ion. For example, when one chlorine atom is present, the P ⫹ 2 mass peak will be about one-third the intensity of the parent peak. When one bromine atom is present, the P ⫹ 2 mass peak will be about the same intensity as the parent peak. The abundance of heavy isotopes is treated in terms of the binomial expansion (a ⫹ b)m, where a is the relative abundance of the light isotope, b is the relative abundance of the heavy isotope, and m is the number of atoms of the particular element present in the molecule. If two bromine atoms are present, the binomial expansion is (a ⫹ b) ⫽ a ⫹ 2ab ⫹ b 2

2

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TABLE 7.75 Isotopic Abundances and Masses of Selected Elements (a) Element 1

H H 12C 13C 14 N 15 N 2

Abundance 99.985 0.015 98.892 1.108 99.63 0.37

Abundances of some polyisotopic elements, % Element 16

O O 18O 28Si 29 Si 30 Si 17

(b) Element 1

H C 14 N 16 O 19 F 28 Si 12

Abundance 99.76 0.037 0.204 92.18 4.71 3.12

Element

Abundance

33

S S 35Cl 37Cl 79 Br 81 Br 34

0.76 4.22 75.53 24.47 50.52 49.48

Selected isotope masses

Mass

Element

Mass

1.0078 12.0000 14.0031 15.9949 18.9984 27.9769

31

30.9738 31.9721 34.9689 55.9349 78.9184 126.9047

P S 35 Cl 56 Fe 79 Br 127 I 32

Now substituting the percent abundance of each isotope (79Br and 81Br) into the expansion, (0.505)2 ⫹ 2(0.505)(0.495) ⫹ (0.495)2 gives

0.255 ⫹ 0.500 ⫹ 0.250

which are the proportions of P : (P ⫹ 2) : (P ⫹ 4), a triplet that is slightly distorted from a 1 : 2 : 1 pattern. When two elements with heavy isotopes are present, the binomial expansion (a ⫹ b)m(c ⫹ d)n is used. Sulfur-34 enhances the P ⫹ 2 peak by 4.2%; silicon-29 enhances the P ⫹ 1 peak by 4.7% and the P ⫹ 2 peak by 3.1%. 7.8.1.3 Exact Mass Differences. If the exact mass of the parent or fragment ions are ascertained with a high-resolution mass spectrometer, this relationship is often useful for combinations of C, H, N, and O (Table 7.75b): Exact mass difference from nearest integral mass ⫹ 0.0051z ⫺ 0.0031y ⫽ number of hydrogens 0.0078 One substitutes integral numbers (guesses) for z (oxygen) and y (nitrogen) until the divisor becomes an integral multiple of the numerator within 0.0002 mass unit. For example, if the exact mass is 177.0426 for a compound containing only C, H, O, and N (note the odd mass which indicates an odd number of nitrogen atoms), then 0.0426 ⫹ 0.0051z ⫺ 0.0031y ⫽ 7 hydrogen atoms 0.0078

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when z ⫽ 3 and y ⫽ 1. The empirical formula is C9H7NO3 since

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177 ⫺ 7(1) ⫺ 1(14) ⫺ 3(16) ⫽ 9 carbon atoms 12 7.8.1.4 Number of Rings and Double Bonds. The total number of rings and double bonds can be determined from the empirical formula (CwHxOzNy) by the relationship 1 2(2w ⫺ x ⫹ y ⫹ z) when covalent bonds comprise the molecular structure. Remember the total number for a benzene ring is four (one ring and three double bonds); a triple bond has two. 7.8.1.5

General Rules

1. If the nominal molecular weight of a compound containing only C, H, O, and N is even, so is the number of hydrogen atoms it contains. 2. If the nominal molecular weight is divisible by four, the number of hydrogen atoms is also divisible by four. 3. When the nominal molecular weight of a compound containing only C, H, O, and N is odd, the number of nitrogen atoms must be odd. 7.8.1.6 Metastable Peaks. If the mass spectrometer has a field-free region between the exit of the ion source and the entrance to the mass analyzer, metastable peaks m* may appear as a weak, diffuse (often humped-shape) peak, usually at a nonintegral mass. The one-step decomposition process takes the general form: Original ion : daughter ion ⫹ neutral fragment The relationship between the original ion and daughter ion is given by m* ⫽

(mass of daughter ion)2 mass of original ion

For example, a metastable peak appeared at 147.9 mass units in a mass spectrum with prominent peaks at 65, 91, 92, 107, 108, 155, 172, and 200 mass units. Try all possible combinations in the above expression. The fit is given by 147.9 ⫽

(172)2 200

which provides this information: 200⫹ : 172⫹ ⫹ 28 The probable neutral fragment lost is either CH2 "CH2 or CO.

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Mass Spectra and Structure

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The mass spectrum is a fingerprint for each compound because no two molecules are fragmented and ionized in exactly the same manner on electron-impact ionization. In reporting mass spectra the data are normalized by assigning the most intense peak (denoted as base peak) a value of 100. Other peaks are reported as percentages of the base peak. A very good general survey for interpreting mass spectral data is given by R. M. Silverstein, G. C. Bassler, and T. C. Morrill, Spectrometric Identification of Organic Compounds, 4th ed., Wiley, New York, 1981. 7.8.2.1

Initial Steps in Elucidation of a Mass Spectrum

1. Tabulate the prominent ion peaks, starting with the highest mass. 2. Usually only one bond is cleaved. In succeeding fragmentations a new bond is formed for each additional bond that is broken. 3. When fragmentation is accompanied by the formation of a new bond as well as by the breaking of an existing bond, a rearrangement process is involved. These will be even mass peaks when only C, H, and O are involved. The migrating atom is almost exclusively hydrogen; six-membered cyclic transition states are most important. 4. Tabulate the probable groups that (a) give rise to the prominent charged ion peaks and (b) list the neutral fragments. 7.8.2.2

General Rules for Fragmentation Patterns

1. Bond cleavage is more probable at branched carbon atoms: tertiary ⬎ secondary ⬎ primary. The positive charge tends to remain with the branched carbon. 2. Double bonds favor cleavage beta to the carbon (but see rule 6). 3. A strong parent peak often indicates a ring. 4. Saturated ring systems lose side chains at the alpha carbon. Upon fragmentation, two ring atoms are usually lost. 5. A heteroatom induces cleavage at the bond beta to it. 6. Compounds that contain a carbonyl group tend to break at this group; the positive charge remains with the carbonyl portion. 7. For linear alkanes, the initial fragment lost is an ethyl group (never a methyl group), followed by propyl, butyl, and so on. An intense peak at mass 43 suggests a chain longer than butane. 8. The presence of Cl, Br, S, and Si can be deduced from the unusual isotopic abundance patterns of these elements. These elements can be traced through the positively charged fragments until the pattern disappears or changes due to the loss of one of these atoms to a neutral fragment. 9. When unusual mass differences occur between some fragments ions, the presence of F (mass difference 19), I (mass difference 127), or P (mass difference 31) should be suspected. 7.8.2.3

Characteristic Low-Mass Fragment Ions Mass 30 ⫽ Primary amines

Masses 31, 45, 59 ⫽ Alcohol or ether

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Masses 19 and 31 ⫽ Alcohol Mass 66 ⫽ Monobasic carboxylic acid Masses 77 and 91 ⫽ Benzene ring 7.8.2.4

Characteristic Low-Mass Neutral Fragments from the Molecular Ion Mass 18 (H2O) ⫽ From alcohols, aldehydes, ketones

Mass 19 (F) and 20 (HF) ⫽ Fluorides Mass 27 (HCN) ⫽ Aromatic nitriles or nitrogen heterocycles Mass 29 ⫽ Indicates either CHO or C2H5 Mass 30 ⫽ Indicates either CH2O or NO Mass 33 (HS) and 34 (H2S) ⫽ Thiols Mass 42 ⫽ CH2CO via rearrangement from a methyl ketone or an aromatic acetate or an aryl-NHCOCH3 group Mass 43 ⫽ C3H7 or CH3CO Mass 45 ⫽ COOH or OC2H5 Table 7.76 is condensed, with permission, from the Catalog of Mass Spectral Data of the American Petroleum Institute Research Project 44. These, and other tables, should be consulted for further and more detailed information. Included in the table are all compounds for which information was available through the C7 compounds. The mass number for the five most important peaks for each compound are listed, followed in each case by the relative intensity in parentheses. The intensities in all cases are normalized to the n-butane 43 peak taken as 100. Another method for expressing relative intensities is to assign the base peak a value of 100 and express the relative intensities of the other peaks as a ratio to the base peak. Taking ethyl nitrate as an example, the tabulated values would be Ethyl nitrate

91(0.01)(P)

46(100)

29(44.2)

30(30.5)

76(24.2)

The compounds are arranged in the table according to their molecular formulas. Each formula is arranged alphabetically, except that C is first if carbon occurs in the molecules, followed by H if it occurs. The formulas are then arranged alphabetically and according to increasing number of atoms of each kind, all C4 compounds being listed before any C5 compounds, and so on. Nearly all these spectra have been recorded using 70-V electrons to bombard the sample molecules.

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TABLE 7.76 Condensed Table of Mass Spectra Mass numbers (and intensities) of: Molecular formula B2H 6 B3 H 6 N3 B5 H 9 CBrClF2 CBr2F2 CCl2F2 CCl3 F CCl4 CF3I CF4 CHBrClF CHBrF2 CHCl3 CHF3 CHN CH2ClF CH 2Cl2 CH 2F2 CH 2O CH 2O2 CH 3Cl CH 3F CH 3I CH 3NO2 CH 4 CH 4O CH 4S CH 5N CO COS CO2 CS2 C 2F4 C 2F6 C 2F6Hg C 2H 2 C 2H 2ClN C 2H 2Cl 2 C 2H 2Cl 2 C 2H 2Cl 4 C 2H 2F2 C 2H 3Cl 3 C 2H 3Cl3 C 2H 3F3 C 2H 3N C 2H 4 C 2H 4BrCl C 2H 4Br2 C 2H 4Cl 2

Name Diborane Triborine triamine Pentaborane Difluorochlorobromomethane Difluorodibromomethane Difluorodichloromethane Fluorotrichloromethane Tetrachloromethane Trifluoroiodomethane Tetrafluoromethane Fluorochlorobromomethane Difluorobromomethane Trichloromethane Trifluoromethane Hydrogen cyanide Fluorochloromethane Dichloromethane Difluoromethane Methanal (formaldehyde) Methanoic acid (formic) Chloromethane Monofluoromethane Indomethane Nitromethane Methane Methanol Methanethiol Aminomethane (methylamine) Carbon monoxide Carbonyl sulfide Carbon dioxide Carbon disulfide Tetrafluoroethene Hexafluoroethane Hexafluorodimethylmercury Ethyne Chloroethanenitrile cis-1,2-Dichloroethene trans-1,2,-Dichloroethene 1,1,2,2-Tetrachloroethane 1,1-Difluoroethene 1,1,1-Trichloroethane 1,1,2-Trichloroethane 1,1,1-Trifluoroethane Ethanenitrile Ethene (ethylene) 1-Chloro-2-bromoethane 1,2-Dibromoethane 1,1-Dichloroethane

Parent peak

Base peak

28(0.13) 81(21) 64(15) 164(0.23) 208(1.7) 120(0.07) 136(0.04) 152(0.0) 196(51) 88(0.0) 148(5.5) 130(13) 118(1.3) 70(0.25) 27(92) 68(48) 84(41) 52(2.7) 30(19) 46(72) 50(66) 34(29) 142(78) 61(35) 16(67) 32(26) 48(49) 31(30) 28(78) 60(83) 44(76) 76(184) 100(20) 138(0.14) 340(0.83) 26(102) 75(51) 96(53) 96(49) 166(5.9) 64(32) 132(0.0) 132(3.9) 84(0.94) 41(89) 28(66) 142(7.9) 186(1.6) 98(5.7)

26(54) 80(58) 59(30) 85(86) 129(70) 85(33) 101(54) 117(39) 196(51) 69(57) 67(120) 51(83) 83(69) 69(20) 27(92) 68(48) 49(71) 33(26) 29(21) 29(118) 50(66) 15(31) 142(78) 30(65) 16(67) 31(38) 47(65) 30(53) 28(78) 60(83) 44(76) 76(184) 31(47) 69(95) 69(111) 26(102) 75(51) 61(72) 61(73) 83(95) 64(32) 97(37) 97(43) 69(81) 41(89) 28(66) 63(93) 27(93) 63(89)

Three next most intense peaks 27(52) 79(37) 60(30) 87(27) 131(68) 87(11) 103(35) 119(37) 127(49) 50(6.8) 69(38) 31(18) 85(44) 51(18) 26(15) 33(25) 86(26) 51(25) 28(6.6) 45(56) 15(54) 33(28) 127(29) 15(34) 15(58) 29(25) 45(40) 28(47) 12(3.7) 32(48) 28(5.0) 32(40) 81(34) 119(39) 202(26) 25(20) 48(46) 98(34) 98(32) 85(60) 45(21) 99(24) 83(41) 65(31) 40(46) 27(43) 27(82) 107(72) 27(64)

24(48) 53(29) 62(24) 129(17) 79(18) 50(3.9) 66(7.0) 35(16) 69(40) 19(3.9) 31(13) 132(13) 47(24) 31(9.9) 12(3.8) 70(15) 51(21) 31(7.3) 14(0.94) 28(20) 52(21) 14(5.3) 141(11) 46(23) 14(11) 28(2.4) 46(9.5) 29(8.7) 16(1.3) 28(6.9) 16(4.7) 44(33) 50(14) 31(17) 271(22) 24(5.7) 40(23) 63(23) 26(25) 95(11) 31(16) 61(19) 99(27) 15(13) 39(17) 26(41) 65(30) 109(67) 65(28)

25(30) 52(22) 61(21) 131(16) 31(18) 101(2.8) 35(5.8) 47(16) 177(16) 31(2.8) 111(11) 79(13) 35(13) 50(2.9) 28(1.6) 49(11) 47(13) 32(2.9) 13(0.92) 17(20) 49(6.6) 31(3.2) 15(10) 29(5.3) 13(5.5) 18(0.7) 15(8.9) 27(8.6) 29(0.9) 12(5.0) 12(1.9) 78(16) 12(3.6) 50(9.6) 200(21) 13(5.7) 77(16) 26(22) 63(23) 87(9.7) 33(13) 117(7.1) 85(26) 45(10) 38(10) 25(7.8) 26(24) 26(23) 26(21)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

7.129

SPECTROSCOPY

top of rh base of rh cap height base of text

TABLE 7.76 Condensed Table of Mass Spectra (Continued) Mass numbers (and intensities) of: Molecular formula C 2H 4Cl2 C 2H 4N2 C 2H 4O C 2H 4O C 2H 4O2 C 2H 4O2 C 2H 5Br C 2H 5Cl C 2H 5F C 2H 5N C 2H 5NO2 C 2H 5NO3 C 2H 6 C 2H 6O C 2H 6O C 2H 6O2 C 2H 6S C 2H 6S C 2H 6S 2 C 2H 6S 3 C 2H 7N C 2H 7N C 2H 8N2 C 3F 6 C 3F 8 C 3H 3N C 3H 4 C 3H 4 C 3H 4ClN C 3H 4O C 3H 5Cl C 3H 5ClO C 3H 5ClO2 C 3H 5Cl 3 C 3H 5N C 3H 6 C 3H 6 C 3H 6Cl 2 C 3H 6Cl 2 C 3H 6O C 3H 6O C 3H 6O C 3H 6O C 3H 6O2 C 3H 6O2 C 3H 6O2 C 3H 6O2 C 3H 6O3 C 3H 7Br

Name 1,2-Dichloroethane Diazoethane Ethanal (acetaldehyde) Ethylene oxide Ethanoic acid (acetic) Methyl formate Bromoethane Chloroethane Fluoroethane Ethylenimine Nitroethane Ethyl nitrate Ethane Ethanol Dimethyl ether Dimethyl peroxide 2-Thiapropane Ethanethiol 2,3-Dithiabutane 2,3,4-Trithiapentane Aminoethane (ethylamine) N-Methylaminomethane 1,2-Diaminoethane Hexafluoropropene Octafluoropropane Propenenitrile Propadiene Propyne (methylacetylene) 3-Chloropropanenitrile Propenal (acrolein) 1-Chloro-1-propene 3-Chloro-1,2-epoxypropane Methyl chloroacetate 1,2,3-Trichloropropane Propanenitrile Cyclopropane Propene 1,1-Dichloropropane 1,2-Dichloropropane 1-Propen-3-ol (allyl alc.) Propanal Propanone (acetone) 1,2-Epoxypropane 1,3-Dioxolane Propanoic acid Ethyl formate Methyl acetate Methyl carbonate 1-Bromopropane

Parent peak

Base peak

98(1.7) 56(16) 44(30) 44(30) 60(19) 60(27) 108(35) 64(36) 48(2.4) 43(31) 75(0.0) 91(0.01) 30(26) 46(9.7) 46(32) 62(28) 62(56) 62(44) 94(95) 126(54) 45(18) 45(36) 60(2.7) 150(16) 188(0.0) 53(55) 40(72) 40(79) 89(12) 56(16) 76(30) 92(0.19) 109(0.23) 146(0.71) 55(8.3) 42(64) 42(39) 112(0.0) 112(2.6) 58(12) 58(25) 58(24) 58(19) 74(3.1) 74(27) 74(5.8) 74(22) 90(3.3) 122(14)

62(12) 28(27) 29(66) 29(46) 43(37) 31(96) 29(54) 64(36) 47(24) 42(56) 29(85) 46(95) 28(99) 31(63) 45(71) 29(47) 47(69) 62(44) 94(95) 126(54) 30(96) 44(71) 30(111) 31(56) 69(171) 26(55) 40(72) 40(79) 49(68) 27(25) 41(70) 57(55) 59(56) 75(61) 28(83) 42(64) 41(58) 63(27) 63(51) 57(43) 29(66) 43(85) 28(44) 73(52) 28(34) 31(82) 43(148) 15(93) 43(94)

Three next most intense peaks 27(11) 27(25) 43(18) 15(30) 45(33) 29(60) 27(48) 28(32) 27(8.9) 28(44) 27(74) 29(42) 27(33) 45(22) 29(56) 31(45) 45(42) 29(43) 45(59) 45(32) 28(28) 28(48) 18(14) 69(44) 31(49) 52(41) 39(69) 39(73) 54(54) 26(15) 39(43) 27(53) 49(44) 110(22) 54(51) 41(58) 39(41) 41(25) 62(36) 29(34) 28(46) 15(26) 29(30) 43(36) 29(28) 28(60) 29(16) 45(54) 27(55)

49(4.9) 26(21) 42(6.1) 14(12) 15(21) 32(33) 110(33) 29(30) 33(8.2) 15(20) 30(19) 30(29) 26(23) 29(14) 15(41) 15(16) 46(29) 47(36) 79(56) 79(27) 44(19) 15(14) 42(6.9) 131(41) 169(42) 51(18) 38(29) 38(29) 51(29) 28(13) 40(10) 29(40) 15(43) 77(19) 26(17) 39(44) 27(22) 77(22) 27(29) 31(26) 27(38) 27(5.9) 27(28) 44(30) 27(21) 29(54) 42(15) 29(43) 41(47)

64(3.9) 41(5.2) 26(6.1) 43(7.1) 14(8.0) 28(6.8) 26(16) 27(27) 26(3.0) 41(11) 26(11) 76(23) 29(21) 27(14) 14(8.9) 30(12) 35(24) 27(35) 46(34) 47(19) 27(13) 42(13) 43(5.9) 100(20) 50(16) 27(10) 37(23) 37(22) 26(20) 55(11) 78(9.6) 31(21) 29(37) 61(18) 27(15) 27(23) 40(17) 62(19) 41(25) 27(19) 26(14) 42(5.9) 26(18) 29(30) 45(19) 27(36) 59(8.4) 31(34) 39(22)

short standard long

DEAN #37261

LEFT

(McGHP)

7.130

INTERACTIVE

top of rh base of rh

SECTION 7

cap height base of text

TABLE 7.76 Condensed Table of Mass Spectra (Continued) Mass numbers (and intensities) of: Molecular formula C 3H 7Br C 3H 7Cl C 3H 7Cl C 3H 7F C 3H 7N C 3H 7N C 3H 7NO C 3H 7NO2 C 3H 7NO2 C 3H 8 C 3H 8O C 3H 8O C 3H 8O C 3H 8O2 C 3H 8O2 C 3H 8S C 3H 8S C 3H 8S C 3H 9N C 3H 9N C 3H 12B3N3 C 4F6 C 4F6 C 4F6 C 4F8 C 4F8 C 4F8 C 4F10 C4 HF7O2 C4 H 2 C4 H 4 C4 H 4O C4 H 4S C4 H 4S2 C4 H 5N C4 H 5N C4 H 6 C4 H 6 C4 H 6 C4 H 6 C4 H 6Cl 2O2 C4 H 6O2 C4 H 6O2 C4 H 7BrO2 C4 H 7Cl C4 H 7ClO2 C4 H 7ClO2 C4 H 7N C4 H 7N

Name 2-Bromopropane 1-Chloropropane 2-Chloropropane 2-Fluoropropane 2-Methylethylenimine N-Methylethylenimine N,N-Dimethylformamide 1-Nitropropane 2-Nitropropane Propane 1-Propanol 2-Propanol Methyl ethyl ether Dimethoxymethane 2-Methoxy-1-ethanol 2-Thiabutane 1-Propanethiol 2-Propanethiol 1-Aminopropane Trimethylamine B,B⬘,B⬙-Trimethylborazole Hexafluorocyclobutene Hexafluoro-1,3-butadiene Hexafluoro-2-butyne Octafluorocyclobutane Octafluoromethylpropene Octafluoro-1-butene Decafluorobutane Heptafluorobutanoic acid 1,3-Butadiyne 1-Buten-3-yne Furan Thiophene 2-Thiophenethiol 3-Butenenitrile Pyrrole 1,2-Butadiene 1,3-Butadiene 1-Butyne 2-Butyne Ethyl dichloroacetate 2,3-Butanedione Methyl 2-propenoate 2-Bromoethyl acetate 2-Chloro-2-butene 2-Chloroethyl acetate Ethyl chloroacetate 2-Methylpropanenitrile n-Butanenitrile

Parent peak

Base peak

122(11) 78(3.6) 78(14) 62(1.0) 57(22) 57(31) 73(54) 89(0.0) 89(0.0) 44(25) 60(7.2) 60(0.45) 60(24) 76(1.6) 76(7.3) 76(47) 76(30) 76(41) 59(1.5) 59(37) 123(30) 162(21) 162(27) 162(18) 200(0.12) 200(14) 200(11) 238(0.0) 214(0.0) 50(133) 52(55) 68(36) 84(93) 116(68) 67(27) 67(67) 54(65) 54(46) 54(64) 54(93) 156(0.12) 86(13) 86(2.0) 166(0.03) 90(27) 122(0.0) 122(0.96) 69(1.7) 69(0.15)

43(100) 42(60) 43(58) 47(84) 28(76) 42(94) 44(63) 43(68) 43(75) 29(85) 31(115) 45(112) 45(94) 45(117) 45(122) 61(73) 47(43) 43(65) 30(20) 58(95) 108(102) 93(80) 93(90) 93(47) 100(97) 69(74) 131(122) 69(178) 45(26) 50(133) 52(55) 39(58) 84(93) 116(68) 41(80) 67(67) 54(65) 39(53) 54(64) 54(93) 29(192) 43(118) 55(98) 43(158) 55(68) 43(162) 29(130) 42(79) 41(112)

Three next most intense peaks 27(50) 29(27) 27(20) 46(24) 56(34) 15(46) 42(29) 27(67) 41(55) 28(50) 27(18) 43(19) 29(46) 29(51) 29(44) 48(40) 43(34) 41(44) 28(2.5) 42(44) 107(77) 31(51) 31(45) 143(38) 131(84) 181(54) 31(86) 119(33) 69(24) 49(57) 51(28) 38(9.7) 58(56) 71(64) 39(36) 39(46) 27(35) 27(36) 39(49) 27(42) 27(58) 15(40) 27(66) 27(35) 27(21) 73(43) 27(41) 68(38) 29(70)

41(47) 27(22) 63(15) 61(12) 30(24) 28(25) 28(25) 41(58) 27(53) 27(33) 29(17) 27(18) 15(23) 75(51) 15(38) 47(30) 27(34) 27(41) 27(1.3) 15(32) 67(38) 143(15) 74(10) 31(25) 31(53) 31(44) 69(44) 31(22) 119(17) 48(14) 50(23) 29(9.3) 45(49) 45(31) 27(30) 41(42) 53(29) 53(31) 53(27) 53(41) 83(23) 14(12) 15(27) 106(31) 39(21) 15(36) 77(37) 28(26) 27(38)

39(24) 41(14) 41(13) 27(7.6) 29(19) 27(17) 15(24) 39(24) 39(23) 43(19) 59(10) 29(11) 27(19) 15(48) 31(32) 27(27) 41(32) 61(26) 41(1.0) 30(17) 66(34) 74(6.9) 112(10) 69(20) 69(24) 93(22) 93(16) 100(15) 100(14) 25(12) 49(7.2) 40(6.7) 39(24) 39(11) 40(20) 40(36) 39(28) 28(24) 27(26) 39(24) 28(19) 42(8.6) 26(22) 108(30) 29(18) 27(29) 49(29) 54(19) 28(11)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

7.131

SPECTROSCOPY

top of rh base of rh cap height base of text

TABLE 7.76 Condensed Table of Mass Spectra (Continued) Mass numbers (and intensities) of: Molecular formula C4 H 8 C4 H 8 C4 H 8 C4 H 8 C4 H 8 C4 H 8Cl 2 C4 H 8Cl 2 C4 H 8Cl 2 C4 H 8Cl 2 C4 H 8N2 C4 H 8O C4 H 8O C4 H 8O C4 H 8O C4 H 8O C4 H 8O C4 H 8O2 C4 H 8O2 C4 H 8O2 C4 H 8O2 C4 H 8O2 C4 H 8O2 C4 H 8O2 C4 H 8S C4 H 8S C4 H 9Br C4 H 9Br C4 H 9N C4 H 9NO2 C4 H 10 C4 H 10 C4 H 10 Hg C4 H 10 O C4 H 10 O C4 H 10 O C4 H 10 O C4 H 10 O C4 H 10 O C4 H 10 O2 C4 H 10 O2 C4 H 10 O2 C4 H 10 O2 C4 H 10 S C4 H 10 S C4 H 10 S C4 H 10 S C4 H 10 S C4 H 10 S C4 H 10 S

Name Cyclobutane 2-Methylpropene 1-Butene cis-2-Butene trans-2-Butene 1,2-Dichlorobutane 1,4-Dichlorobutane dl-2,3-Dichlorobutane meso-2,3-Dichlorobutane Acetaldazine Butanal 2-Butanone Ethyl ethenyl ether cis-2,3-Epoxybutane trans-2,3-Epoxybutane Tetrahydrofuran 2-Methyl-1,3-dioxacyclopentane 1,4-Dioxane 2-Methylpropanoic acid n-Butanoic acid n-Propyl formate Ethyl acetate Methyl propanoate 3-Methylthiacyclobutane Thiacyclopentane 1-Bromobutane 2-Bromobutane Pyrrolidine n-Butyl nitrite 2-Methylpropane n-Butane Diethylmercury 2-Methyl-1-propanol 2-Methyl-2-propanol 1-Butanol 2-Butanol Diethyl ether Methyl isopropyl ether 1,1-Dimethoxyethane 1,2-Dimethoxyethane 2-Ethoxyethanol Diethyl peroxide 3-Methyl-2-thiabutane 2-Thiapentane 3-Thiapentane 2-Methyl-1-propanethiol 2-Methyl-2-propanethiol 1-Butanethiol 2-Butanethiol

Parent peak

Base peak

56(41) 56(36) 56(32) 56(36) 56(37) 126(0.30) 126(0.03) 126(0.95) 126(0.95) 84(23) 72(19) 72(17) 72(27) 72(3.6) 72(3.5) 72(22) 88(0.33) 88(42) 88(8.1) 88(1.0) 88(0.41) 88(7.1) 88(23) 88(42) 88(44) 136(7.0) 136(0.72) 71(24) 103(0.0) 58(3.2) 58(12) 260(12) 74(7.5) 74(0.0) 74(0.37) 74(0.30) 74(22) 74(8.3) 90(0.06) 90(12) 90(0.49) 90(20) 90(41) 90(58) 90(41) 90(35) 90(34) 90(40) 90(34)

28(65) 41(85) 41(87) 41(76) 41(80) 41(39) 55(87) 63(63) 63(64) 42(92) 27(41) 43(97) 44(64) 43(67) 43(69) 42(76) 73(67) 28(138) 43(77) 60(40) 31(123) 43(181) 29(110) 46(101) 60(82) 57(86) 57(108) 43(102) 27(55) 43(117) 43(100) 29(188) 43(84) 59(92) 31(52) 45(116) 31(73) 59(126) 59(93) 45(177) 31(112) 29(116) 41(49) 61(126) 75(59) 41(60) 41(68) 56(74) 41(56)

Three next most intense peaks 41(58) 39(37) 39(30) 39(27) 27(27) 77(35) 41(29) 62(58) 27(57) 15(47) 29(38) 29(24) 43(56) 44(39) 44(35) 41(39) 43(48) 29(51) 41(33) 73(12) 42(89) 29(46) 57(83) 45(31) 45(29) 41(63) 41(65) 28(38) 43(54) 41(45) 29(44) 27(54) 31(56) 31(31) 56(44) 31(23) 59(34) 29(42) 29(52) 29(53) 29(57) 15(42) 75(47) 48(50) 47(51) 43(46) 57(61) 41(65) 57(50)

27(27) 28(18) 27(26) 27(25) 39(26) 27(20) 27(24) 27(57) 62(54) 28(46) 44(34) 27(15) 29(49) 27(35) 29(32) 27(25) 45(44) 58(33) 27(26) 27(9.6) 29(38) 45(24) 27(40) 39(24) 46(29) 29(50) 29(61) 70(33) 41(50) 42(39) 27(37) 28(21) 42(48) 41(19) 41(31) 59(22) 29(29) 43(37) 15(37) 15(50) 59(56) 45(34) 43(41) 41(43) 27(39) 56(34) 29(44) 27(42) 61(46)

26(15) 27(17) 28(26) 28(24) 28(26) 76(16) 90(23) 55(29) 55(31) 69(38) 43(32) 57(6.0) 27(43) 29(33) 27(31) 71(20) 29(34) 31(24) 73(19) 41(9.1) 27(36) 27(24) 59(27) 47(21) 47(22) 27(46) 27(36) 42(20) 30(47) 27(33) 28(33) 231(15) 41(47) 43(14) 43(30) 27(20) 45(28) 15(32) 31(37) 60(16) 27(31) 62(30) 48(38) 27(43) 61(33) 47(29) 39(21) 47(31) 29(46)

short standard long

DEAN #37261

LEFT

(McGHP)

7.132

INTERACTIVE

top of rh base of rh

SECTION 7

cap height base of text

TABLE 7.76 Condensed Table of Mass Spectra (Continued) Mass numbers (and intensities) of: Molecular formula C4 H 10 S2 C4 H 10 S2 C4 H 10 SO3 C4 H 11 N C4 H 11 N C4 H 11 N C4 H 11 N C4 H 11 N C4 H 12Pb C 5F10 C 5F12 C 5F12 C 5 HF9 C 5 H5 N C 5 H6 C 5 H6 C 5 H6N2 C 5 H6O2 C 5 H 6S C 5 H 6S C 5 H8 C 5 H8 C 5 H8 C 5 H8 C 5 H8 C 5 H8 C 5 H8 C 5 H8 C 5 H8 C 5 H8 C 5 H8 C 5 H8 C 5 H8 C 5 H8N2 C 5 H8O2 C 5 H8O2 C 5 H8O2 C 5 H9ClO2 C 5 H10 C 5 H10 C 5 H10 C 5 H10 C 5 H10 C 5 H10 C 5 H10 C 5 H10 C 5 H10 C 5 H10 C 5 H10O

Name 2,3-Dithiahexane 3,4-Dithiahexane Ethyl sulfite N-Ethylaminoethane 1-Amino-2-methylpropane 2-Amino-2-methylpropane 1-Aminobutane 2-Aminobutane Tetramethyllead Decafluorocyclopentane Dodecafluoro-2-methylbutane Dodecafluoropentane Nonafluorocyclopentane Pyridine Cyclopentadiene trans-2-Penten-4-yne 2-Methylpyrazine Furfuryl alcohol 2-Methylthiophene 3-Methylthiophene Methylenecyclobutane Spiropentane Cyclopentene 3-Methyl-1,2-butadiene 2-Methyl-1,3-butadiene 1,2-Pentadiene cis-1,3-Pentadiene trans-1,3-Pentadiene 1,4-Pentadiene 2,3-Pentadiene 3-Methyl-1-butyne 1-Pentyne 2-Pentyne 3,5-Dimethylpyrazole 2,4-Pentanedione 2-Propenyl acetate Methyl methacrylate Ethyl 3-chloropropanoate cis-1,2-Dimethylcyclopropane trans-1,2-Dimethylcyclopropane Ethylcyclopropane Cyclopentane 2-Methyl-1-butene 3-Methyl-1-butene 2-Methyl-2-butene 1-Pentene cis-2-Pentene trans-2-Pentene 3-Methyl-1-butanal

Parent peak

Base peak

122(37) 122(73) 138(3.3) 73(17) 73(1.0) 73(0.25) 73(12) 73(1.2) 268(0.14) 250(0.62) 288(0.0) 288(0.08) 232(0.07) 79(135) 66(95) 66(77) 94(81) 98(3.4) 98(68) 98(74) 68(38) 68(8.9) 68(41) 68(53) 68(40) 68(39) 68(40) 68(41) 68(40) 68(62) 68(8.5) 68(8.7) 68(67) 96(47) 100(22) 100(0.16) 100(26) 136(0.70) 70(39) 70(42) 70(26) 70(44) 70(30) 70(26) 70(31) 70(27) 70(30) 70(31) 86(3.0)

80(53) 29(82) 29(131) 58(83) 30(22) 58(127) 30(200) 44(170) 253(69) 131(173) 69(277) 69(259) 131(61) 79(135) 66(95) 66(77) 94(81) 98(3.4) 97(125) 97(138) 40(67) 67(58) 67(99) 68(53) 67(48) 68(39) 67(53) 67(52) 39(47) 68(62) 53(74) 67(50) 68(67) 96(47) 43(120) 43(177) 41(78) 27(65) 55(77) 55(79) 42(93) 42(148) 55(97) 55(102) 55(88) 42(89) 55(89) 55(93) 41(30)

Three next most intense peaks 43(36) 66(81) 31(59) 30(81) 28(2.0) 41(26) 28(23) 18(25) 223(59) 100(41) 119(45) 119(76) 113(49) 52(95) 65(40) 39(54) 67(48) 41(3.3) 45(26) 45(35) 67(48) 40(56) 39(36) 53(40) 53(41) 53(38) 39(43) 39(43) 67(35) 53(42) 67(45) 40(44) 53(61) 95(37) 85(33) 41(30) 69(52) 29(62) 42(35) 42(34) 55(47) 55(43) 42(36) 27(31) 41(31) 55(53) 42(41) 42(41) 43(26)

41(27) 27(57) 45(42) 28(30) 41(1.2) 42(20) 27(16) 41(18) 208(46) 31(40) 131(23) 169(25) 69(34) 51(48) 39(35) 65(38) 26(33) 39(3.3) 39(17) 39(14) 39(47) 39(52) 53(23) 39(28) 39(34) 39(37) 53(38) 53(39) 53(33) 39(36) 27(35) 39(42) 39(32) 39(16) 15(23) 39(29) 39(31) 91(42) 39(32) 41(33) 41(39) 41(43) 39(34) 42(28) 39(28) 41(39) 39(30) 39(30) 58(20)

27(25) 94(53) 27(39) 27(24) 27(1.1) 15(18) 18(12) 58(18) 251(36) 69(28) 31(18) 31(24) 31(19) 50(35) 40(30) 40(35) 39(30) 42(2.6) 53(11) 27(11) 53(21) 53(23) 41(19) 41(26) 27(23) 27(31) 41(25) 41(26) 41(30) 41(31) 39(21) 27(34) 27(27) 54(12) 27(11) 15(28) 15(16) 63(37) 41(32) 39(30) 39(35) 39(31) 41(28) 29(27) 42(27) 39(31) 29(26) 41(28) 29(20)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

7.133

SPECTROSCOPY

top of rh base of rh cap height base of text

TABLE 7.76 Condensed Table of Mass Spectra (Continued) Mass numbers (and intensities) of: Molecular formula C 5 H10O C 5 H10O C 5 H10O C 5 H10O C 5 H10O C 5 H10O2 C 5 H10O2 C 5 H10O2 C 5 H10O2 C 5 H10O2 C 5 H10O2 C 5 H10O2 C 5 H10O2 C 5 H10O2 C 5 H10O2 C 5 H10O2 C 5 H10O2 C 5 H10O3 C 5 H10S C 5 H10S C 5 H10S C 5 H10S C 5 H11N C 5 H11NO C 5 H11NO2 C 5 H12 C 5 H12 C 5 H12 C 5 H12O C 5 H12O C 5 H12O C 5 H12O C 5 H12O C 5 H12O C 5 H12O C 5 H12O C 5 H12O C 5 H12O2 C 5 H12O2 C 5 H12S C 5 H12S C 5 H12S C 5 H12S C 5 H12S C 5 H12S C 5 H12S C 5 H12S C 5 H12S C 5 H12S

Name 2-Pentanone 3-Pentanone Ethyl-2-propenyl ether Ethyl isopropyl ether 2-Methyltetrahydrofuran Tetrahydrofurfuryl alcohol 2-Methoxyethyl ethenyl ether 2,2-Dimethylpropanoic acid 2-Methylbutanoic acid n-Butyl formate Isobutyl formate sec-Butyl formate n-Propyl acetate Isopropyl acetate Ethyl propanoate Methyl 2-methylpropanoate Methyl butanoate Ethyl carbonate 2-Methylthiacyclopentane 3-Methylthiacyclopentane Thiacyclohexane Cyclopentanethiol Piperidine N-Methylmorpholine 3-Methylbutyl nitrite 2,2-Dimethylpropane 2-Methylbutane n-Pentane 2-Methyl-1-butanol 3-Methyl-1-butanol 2-Methyl-2-butanol 1-Pentanol Methyl n-butyl ether Methyl isobutyl ether Methyl sec-butyl ether Methyl tert-butyl ether Ethyl isopropyl ether Diethoxymethane 1,1-Dimethoxypropane 3,3-Dimethyl-2-thiabutane 4-Methyl-2-thiapentane 2-Methyl-3-thiapentane 2-Thiahexane 3-Thiahexane 2,2-Dimethyl-1-propanethiol 2-Methyl-1-butanethiol 2-Methyl-2-butanethiol 3-Methyl-2-butanethiol 1-Pentanethiol

Parent peak

Base peak

86(16) 86(15) 86(6.2) 86(21) 86(8.9) 102(0.02) 102(3.0) 102(2.0) 102(0.32) 102(0.27) 102(0.27) 102(0.17) 102(0.07) 102(0.17) 102(10) 102(8.9) 102(1.0) 118(0.30) 102(37) 102(40) 102(43) 102(19) 85(22) 101(4.4) 117(0.0) 72(0.01) 72(4.7) 72(10) 88(0.18) 88(0.02) 88(0.0) 88(0.0) 88(3.1) 88(12) 88(2.0) 88(0.02) 88(2.6) 104(2.1) 104(0.05) 104(30) 104(37) 104(82) 104(38) 104(30) 104(31) 104(28) 104(18) 104(23) 104(35)

43(106) 57(87) 41(52) 43(87) 71(57) 71(8.9) 29(69) 57(83) 74(54) 56(80) 43(58) 45(99) 43(176) 43(155) 29(151) 43(69) 43(53) 29(114) 87(88) 60(45) 87(44) 41(48) 84(43) 43(18) 29(75) 57(126) 43(74) 43(114) 57(57) 55(47) 59(43) 42(41) 45(211) 45(186) 52(142) 73(119) 45(143) 31(104) 75(84) 57(83) 41(46) 89(119) 61(77) 75(72) 57(100) 41(65) 43(88) 61(73) 42(91)

Three next most intense peaks 29(23) 29(87) 29(48) 44(69) 43(55) 43(6.8) 45(58) 41(38) 57(34) 41(48) 56(48) 29(49) 61(34) 45(50) 57(97) 71(23) 74(37) 45(80) 41(30) 41(31) 68(33) 69(47) 57(22) 42(8.6) 41(68) 41(52) 42(64) 42(66) 29(55) 42(42) 55(37) 55(30) 56(36) 41(30) 29(50) 41(33) 43(46) 59(99) 73(62) 41(62) 56(38) 62(79) 56(50) 27(53) 41(55) 29(44) 71(54) 43(55) 55(44)

27(23) 27(32) 58(44) 41(46) 41(40) 41(4.8) 15(48) 29(27) 29(33) 31(47) 41(46) 27(32) 31(31) 27(22) 27(52) 41(19) 71(29) 31(60) 45(29) 45(25) 61(32) 39(26) 56(22) 15(3.4) 57(43) 29(49) 41(49) 41(45) 41(53) 43(39) 45(25) 41(25) 29(36) 29(30) 27(27) 43(32) 73(40) 29(62) 29(43) 29(42) 27(29) 43(63) 41(39) 47(50) 55(48) 57(40) 41(46) 27(33) 41(39)

57(20) 28(9.4) 57(42) 27(45) 27(27) 27(3.8) 58(45) 39(12) 41(28) 29(42) 31(38) 41(31) 27(26) 61(18) 28(24) 59(17) 27(23) 27(46) 59(18) 74(23) 41(28) 67(18) 44(17) 71(2.9) 30(42) 27(20) 57(40) 27(39) 56(50) 41(38) 73(22) 70(23) 27(28) 15(27) 41(25) 57(32) 27(24) 103(39) 45(37) 39(16) 39(23) 61(58) 27(33) 62(33) 29(42) 70(40) 55(34) 55(28) 70(39)

short standard long

DEAN #37261

LEFT

(McGHP)

7.134

INTERACTIVE

top of rh base of rh

SECTION 7

cap height base of text

TABLE 7.76 Condensed Table of Mass Spectra (Continued) Mass numbers (and intensities) of: Molecular formula C 5 H12S C 5 H12S C 5 H12S2 C 5 H12S2 C 5 H14Pb C6 F6 C6 F12 C6 F14 C6 F14 C 6 H5 Br C 6 H5 Cl C 6 H5 NO2 C6H6 C6H6 C6H6 C 6 H 6S C 6 H 7N C 6 H 7N C 6 H 7NO C6H8 C6H8 C 6 H 8O C 6 H 8S C 6 H 8S C 6 H 8S C 6 H 8S C 6 H 8S C 6 H 9N C 6 H 10 C 6 H 10 C 6 H 10 C 6 H 10 C 6 H 10 C 6 H 10 C 6 H 10 C 6 H 10 C 6 H 10 C 6 H 10 C 6 H 10 C 6 H 10O C 6 H 10O C 6 H 10O2 C 6 H 10O3 C 6 H 10O3 C 6 H 11N C 6 H 11N C 6 H 12 C 6 H 12 C 6 H 12

Name 2-Pentanethiol 3-Pentanethiol 4,4-Dimethyl-2,3-dithiapentane 2-Methyl-3,4-dithiahexane Trimethylethyllead Hexafluorobenzene Dodecafluorocyclohexane Tetradecafluoro-2-methylpentane Tetradecafluorohexane Bromobenzene Chlorobenzene Nitrobenzene Benzene 1,5-Hexadiyne 2,4-Hexadiyne Benzenethiol Aminobenzene (aniline) 2-Methylpyridine 1-Methyl-2-pyridone Methylcyclopentadiene 1,3-Cyclohexadiene 2.5-Dimethylfuran 2,3-Dimethylthiophene 2,4-Dimethylthiophene 2,5-Dimethylthiophene 2-Ethylthiophene 3-Ethylthiophene 2,5-Dimethylpyrrole Isopropenylcyclopropane 1-Methylcyclopentene Cyclohexene 2,3-Dimethyl-1,3-butadiene 2-Methyl-1,3-pentadiene 1,5-Hexadiene 3,3-Dimethyl-1-butyne 4-Methyl-1-pentyne 1-Hexyne 2-Hexyne 3-Hexyne Cyclohexanone 4-Methyl-3-penten-2-one 2,5-Hexanedione Propanoic anhydride Ethyl acetoacetate 4-Methylpentanenitrile Hexanenitrile 1,1,2-Trimethylcyclopropane 1-Methyl-1-ethylcyclopropane Isopropylcyclopropane

Parent peak

Base peak

104(28) 104(23) 136(12) 136(20) 282(0.64) 186(95) 300(0.96) 338(0.0) 338(0.13) 156(75) 112(102) 123(39) 78(113) 78(58) 78(108) 110(68) 93(19) 93(86) 109(71) 80(53) 80(53) 96(57) 112(44) 112(27) 112(67) 112(27) 112(54) 95(73) 82(20) 82(26) 82(33) 82(41) 82(23) 82(1.3) 82(0.57) 82(2.3) 82(1.0) 82(56) 82(55) 98(32) 98(40) 114(4.0) 130(0.0) 130(8.3) 97(0.13) 97(0.54) 84(38) 84(25) 84(2.0)

43(72) 43(56) 57(74) 94(49) 223(61) 186(95) 131(138) 69(317) 69(268) 77(98) 112(102) 77(93) 78(113) 39(65) 78(108) 110(68) 93(19) 93(86) 109(71) 79(87) 79(92) 43(65) 97(53) 111(36) 111(95) 97(68) 97(147) 94(127) 67(92) 67(98) 67(83) 67(60) 67(48) 41(98) 67(101) 67(82) 67(131) 67(58) 67(59) 55(102) 55(82) 43(148) 57(190) 43(150) 55(98) 41(73) 41(132) 41(78) 56(114)

Three next most intense peaks 61(52) 41(48) 41(38) 27(46) 253(52) 117(59) 69(97) 131(41) 119(74) 158(74) 77(49) 51(55) 52(22) 52(38) 51(55) 66(26) 66(6.5) 66(36) 81(49) 77(29) 77(35) 95(48) 111(44) 97(18) 97(59) 45(16) 45(38) 26(52) 41(47) 39(21) 54(64) 39(55) 39(30) 67(80) 41(57) 41(74) 41(88) 53(50) 41(55) 42(86) 83(82) 15(25) 29(119) 29(52) 41(51) 54(49) 69(81) 55(58) 41(84)

27(39) 75(29) 29(36) 43(39) 208(51) 31(58) 100(40) 119(36) 169(51) 51(41) 114(33) 50(23) 77(20) 51(32) 52(38) 109(17) 65(3.6) 39(28) 39(34) 39(19) 39(21) 53(37) 45(16) 45(9.4) 59(23) 39(8.9) 39(20) 80(22) 39(46) 81(16) 41(31) 41(44) 41(26) 39(60) 39(31) 43(64) 27(85) 27(39) 39(37) 41(35) 43(64) 99(22) 27(62) 27(32) 43(45) 27(43) 39(34) 69(53) 39(30)

55(38) 47(23) 80(13) 66(37) 221(33) 93(23) 31(30) 169(29) 131(37) 50(36) 51(17) 30(15) 51(18) 50(26) 50(31) 51(15) 39(3.5) 51(16) 80(29) 51(11) 27(18) 81(24) 27(9.4) 39(7.0) 45(19) 27(5.4) 27(12) 42(19) 27(22) 41(16) 39(30) 54(22) 27(13) 54(52) 27(11) 39(55) 43(67) 41(36) 53(20) 27(34) 29(38) 14(14) 28(26) 15(27) 27(39) 55(40) 27(24) 27(33) 43(28)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

7.135

SPECTROSCOPY

top of rh base of rh cap height base of text

TABLE 7.76 Condensed Table of Mass Spectra (Continued) Mass numbers (and intensities) of: Molecular formula C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12 C 6 H 12N2 C 6 H 12O C 6 H 12O C 6 H 12O C 6 H 12O C 6 H 12O2 C 6 H 12O2 C 6 H 12O2 C 6 H 12O2 C 6 H 12O2 C 6 H 12O2 C 6 H 12O3 C 6 H 12S C 6 H 12S C 6 H 12S C 6 H 12S C 6 H 12S C 6 H 12S C 6 H 12S C 6 H 12S C 6 H 12S C 6 H 12S C 6 H 12S C 6 H 13N C 6 H 13N C 6 H 13NO C 6 H 14 C 6 H 14

Name Ethylcyclobutane Methylcyclopentane Cyclohexane 2,3-Dimethyl-1-butene 3,3-Dimethyl-1-butene 2-Ethyl-1-butene 2,3-Dimethyl-2-butene 2-Methyl-1-pentene 3-Methyl-1-pentene 4-Methyl-1-pentene 2-Methyl-2-pentene 3-Methyl-cis-2-pentene 3-Methyl-trans-2-pentene 4-Methyl-cis-2-pentene 4-Methyl-trans-2-pentene 1-Hexene cis-2-Hexene trans-2-Hexene cis-3-Hexene trans-3-Hexene Acetone azine (ketazine) Cyclopentylmethanol 4-Methyl-2-pentanone Ethenyl n-butyl ether Ethenyl isobutyl ether 4-Hydroxy-4-methyl-2-pentanone n-Butyl acetate n-Propyl propanoate Isopropyl proponoate Methyl 2,2-dimethylpropanoate Ethyl butanoate 2,4,6-Trimethyl-1,3,5-trioxacyclohexane 1-Cyclopentyl-1-thiaethane cis-2,5-Dimethylthiacyclopentane trans-2.5-Dimethylthiacyclopentane 2-Methylthiacyclohexane 3-Methylthiacyclohexane 4-Methylthiacyclohexane Thiacycloheptane 1-Methylcyclopentanethiol cis-2-Methylcyclopentanethiol trans-2-Methylcyclopentanethiol Cyclohexanethiol Cyclohexylamine 3-Methylpiperidine N-Ethylmorpholine 2,2-Dimethylbutane 2,3-Dimethylbutane

Parent peak

Base peak

84(3.8) 84(18) 84(58) 84(27) 84(23) 84(30) 84(32) 84(29) 84(25) 84(12) 84(36) 84(37) 84(38) 84(35) 84(34) 84(20) 84(27) 84(32) 84(28) 84(32) 112(31) 100(0.02) 100(12) 100(5.7) 100(5.8) 116(0.0) 116(0.03) 116(0.03) 116(0.26) 116(3.2) 116(2.2)

56(138) 56(116) 56(75) 41(117) 41(112) 41(74) 41(108) 56(91) 55(85) 43(110) 41(120) 41(104) 41(102) 41(122) 41(123) 41(70) 55(91) 55(112) 55(81) 55(89) 56(99) 41(35) 43(115) 29(80) 29(73) 43(149) 43(172) 57(147) 57(116) 57(85) 43(50)

41(89) 41(74) 41(44) 69(96) 69(107) 69(66) 69(88) 41(73) 41(67) 41(80) 69(111) 69(82) 69(81) 69(114) 69(112) 56(60) 42(51) 42(54) 41(62) 41(72) 15(31) 68(32) 58(37) 41(59) 41(65) 15(45) 56(58) 29(84) 43(88) 41(32) 71(45)

27(35) 69(37) 55(25) 39(36) 39(28) 55(56) 39(35) 55(39) 69(60) 56(47) 39(35) 55(46) 55(47) 39(35) 39(34) 42(52) 41(45) 41(46) 42(54) 42(62) 97(31) 69(31) 41(22) 56(45) 57(58) 58(32) 41(30) 27(57) 29(54) 29(24) 29(43)

55(34) 42(33) 42(21) 27(24) 27(26) 27(38) 27(20) 39(36) 27(43) 27(37) 27(28) 27(36) 27(35) 27(26) 27(26) 27(48) 27(45) 27(41) 27(32) 27(35) 39(26) 67(24) 57(22) 57(35) 56(40) 27(14) 27(27) 75(47) 27(46) 56(21) 27(31)

132(0.12) 116(31) 116(32) 116(32) 116(42) 116(41) 116(46) 116(60) 116(20) 116(32) 116(28) 116(21) 99(8.9) 99(23) 115(2.0) 86(0.04) 86(5.3)

45(196) 68(72) 101(85) 101(85) 101(81) 101(55) 116(46) 87(75) 83(76) 55(55) 67(48) 55(56) 56(92) 44(49) 42(9.8) 43(85) 43(157)

43(107) 41(64) 59(34) 59(34) 41(37) 41(47) 101(44) 41(66) 55(58) 83(54) 55(46) 41(45) 43(25) 30(34) 57(7.0) 57(82) 42(136)

29(35) 39(37) 41(26) 74(25) 27(32) 39(33) 41(40) 67(48) 41(39) 60(48) 41(42) 67(35) 28(13) 28(27) 100(5.2) 71(61) 41(49)

89(23) 67(37) 74(24) 41(25) 67(30) 45(28) 27(39) 47(46) 67(33) 41(47) 83(40) 83(32) 30(13) 57(26) 28(4.3) 41(51) 27(40)

Three next most intense peaks

short standard long

DEAN #37261

LEFT

(McGHP)

7.136

INTERACTIVE

top of rh base of rh

SECTION 7

cap height base of text

TABLE 7.76 Condensed Table of Mass Spectra (Continued) Mass numbers (and intensities) of: Molecular formula C 6 H 14 C 6 H 14 C 6 H 14 C 6 H 14N2 C 6 H 14O C 6 H 14O C 6 H 14O C 6 H 14O C 6 H 14O C 6 H 14O C 6 H 14O C 6 H 14O C 6 H 14O C 6 H 14O2 C 6 H 14O2 C 6 H 14O3 C 6 H 14S C 6 H 14S C 6 H 14S C 6 H 14S C 6 H 14S C 6 H 14S C 6 H 14S C 6 H 14S C 6 H 14S C 6 H 14S C 6 H 14S C 6 H 14S C 6 H 14S2 C 6 H 14S2 C 6 H 14S2 C 6 H 14S2 C 6 H 15N C 6 H 15N C 6 H 15N C 6 H 16Pb C 7 F14 C 7 F16 C 7H 5 N C 7H 7 Br C 7H 7 Br C 7H 7 Cl C 7H 7 Cl C 7H 7 Cl C 7H 7 F C 7H 7 F C 7H 8 C 7H 8S C 7H 9N

Name

Parent peak

Base peak

2-Methylpentane 3-Methylpentane n-Hexane cis-2,5-Dimethylpiperazine 2-Ethyl-1-butanol 2-Methyl-1-pentanol 3-Methyl-1-pentanol 4-Methyl-2-pentanol 1-Hexanol Ethyl n-butyl ether Ethyl sec-butyl ether Ethyl isobutyl ether Diisopropyl ether 1,1-Diethoxyethane 1,2-Diethoxyethane bis-(2-Methoxyethyl) ether 2,2-Dimethyl-3-thiapentane 2,4-Dimethyl-3-thiapentne 2-Methyl-3-thiahexane 4-Methyl-3-thiahexane 5-Methyl-3-thiahexane 3-Thiaheptane 4-Thiaheptane 2-Methyl-1-pentanethiol 4-Methyl-1-pentanethiol 4-Methyl-2-pentanethiol 2-Methyl-3-pentanethiol 1-Hexanethiol 2,5-Dimethyl-3,4-dithiahexane 5-Methyl-3,4-dithiaheptane 6-Methyl-3,4-dithiaheptane 4,5-Dithiaoctane Triethylamine Di-n-propylamine Diisopropylamine Dimethyldiethyllead Tetradecafluoromethylcyclohexane Hexadecafluoroheptane Benzonitrile 1-Methyl-2-bromobenzene 1-Methyl-4-bromobenzene 1-Methyl-2-chlorobenzene 1-Methyl-3-chlorobenzene 1-Methyl-4-chlorobenzene 1-Methyl-3-fluorobenzene 1-Methyl-4-fluorobenzene Methylbenzene (toluene) 1-Phenyl-1-thiaethane 2,4-Dimethylpyridine

86(4.4) 86(3.2) 86(12) 114(0.38) 102(0.0) 102(0.0) 102(0.0) 102(0.08) 102(0.0) 102(3.8) 102(1.5) 102(8.7) 102(1.4) 118(0.0) 118(1.2) 134(0.0) 118(33) 118(33) 118(206) 118(195) 118(171) 118(35) 118(47) 118((19) 118(30) 118(6.3) 118(20) 118(16) 150(31) 150(14) 150(4.9) 150(44) 101(21) 101(7.1) 101(5.0) 296(0.98) 350(0.0) 388(0.0) 103(246) 170(48) 170(46) 126(44) 126(51) 126(44) 110(79) 110(73) 92(82) 124(76) 107(76)

43(147) 57(105) 57(87) 58(10) 43(114) 42(110) 56(26) 45(111) 56(63) 59(108) 45(150) 59(124) 45(125) 45(132) 31(124) 59(140) 57(147) 43(94) 43(540) 89(585) 75(520) 75(55) 43(86) 43(96) 56(142) 43(68) 41(64) 56(66) 43(152) 29(86) 29(42) 43(167) 86(134) 30(89) 44(171) 267(89) 69(244) 69(330) 103(246) 91(97) 91(97) 91(121) 91(120) 91(120) 109(129) 109(122) 91(108) 124(76) 107(76)

Three next most intense peaks 42(78) 56(80) 43(71) 28(7.7) 70(40) 41(40) 41(20) 43(34) 43(52) 31(87) 73(76) 31(95) 43(66) 73(69) 59(88) 29(74) 41(70) 61(85) 41(317) 29(343) 41(230) 29(33) 89(74) 41(51) 41(57) 69(61) 43(63) 41(41) 108(41) 94(66) 66(40) 27(65) 30(46) 72(70) 86(52) 223(83) 131(107) 119(89) 76(80) 172(46) 172(45) 63(20) 63(19) 125(19) 83(17) 83(16) 39(20) 109(34) 106(29)

41(47) 41(67) 41(64) 30(4.7) 29(39) 29(34) 29(19) 41(17) 41(37) 29(61) 29(51) 29(53) 87(23) 29(36) 29(72) 58(57) 29(54) 41(48) 42(301) 27(296) 47(224) 27(33) 41(57) 56(32) 43(57) 41(56) 75(50) 27(40) 41(36) 66(57) 122(30) 41(64) 27(36) 44(36) 58(24) 208(79) 181(48) 169(68) 50(42) 39(21) 39(20) 39(19) 39(18) 63(18) 57(12) 57(12) 65(14) 78(25) 79(16)

27(40) 29(64) 29(55) 44(4.2) 27(38) 27(33) 55(18) 27(14) 55(36) 27(42) 27(39) 27(38) 27(19) 27(27) 45(53) 15(56) 27(40) 103(44) 27(287) 41(279) 56(217) 62(28) 27(55) 27(31) 27(32) 84(42) 27(28) 43(38) 27(30) 27(41) 94(29) 108(35) 58(35) 43(28) 42(22) 221(44) 100(38) 131(44) 51(24) 63(20) 65(19) 89(18) 128(16) 39(17) 39(12) 39(9.3) 51(10) 91(19) 92(13)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

7.137

SPECTROSCOPY

top of rh base of rh cap height base of text

TABLE 7.76 Condensed Table of Mass Spectra (Continued) Mass numbers (and intensities) of: Molecular formula C 7H 10S C 7H 12 C 7H 12 C 7H 12 C 7H 12 C 7H 12 C 7H 12 C 7H 12 C 7H 12 C 7H 12 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14 C 7H 14O

Name 2,3,4-Trimethylthiophene Ethenylcyclopentane Ethylidenecyclopentane Bicyclo[2.2.1]heptane 3-Ethylcyclopentene 1-Methylcyclohexene 4-Methylcyclohexene 4-Methyl-2-hexyne 5-Methyl-2-hexyne 1-Heptyne 1,1,2,2,-Tetramethylcyclopropane cis-1,2-Dimethylcyclopentane trans-1,2-Dimethylcyclopentane cis-1,3-Dimethylcyclopentane trans-1,3-Dimethylcyclopentane 1,1-Dimethylcyclopentane Ethylcyclopentane Methylcyclohexane Cycloheptane 2,3,3-Trimethyl-1-butene 3-Methyl-2-ethyl-1-butene 2,3-Dimethyl-1-pentene 2,4-Dimethyl-1-pentene 3,3-Dimethyl-1-pentene 3,4-Dimethyl-1-pentene 4,4-Dimethyl-1-pentene 3-Ethyl-1-pentene 2,3-Dimethyl-2-pentene 2,4-Dimethyl-2-pentene 3,4-Dimethyl-cis-2-pentene 3,4-Dimethyl-trans-2-pentene 4,4-Dimethyl-cis-2-pentene 4,4-Dimethyl-trans-2-pentene 3-Ethyl-2-pentene 2-Methyl-1-hexene 3-Methyl-1-hexene 4-Methyl-1-hexene 5-Methyl-1-hexene 2-Methyl-2-hexene 3-Methyl-cis-2-hexene 4-Methyl-trans-2-hexene 5-Methyl-2-hexene 2-Methyl-trans-3-hexene 3-Methyl-cis-3-hexene 3-Methyl-trans-3-hexene 1-Heptene trans-2-Heptene trans-3-Heptene 2,4-Dimethyl-3-pentanone

Parent peak

Base peak

126(50) 96(13) 96(40) 96(12) 96(29) 96(32) 96(28) 96(13) 96(42) 96(0.44) 98(21) 98(19) 98(25) 98(12) 98(13) 98(6.7) 98(14) 98(41) 98(37) 98(20) 98(22) 98(13) 98(9.1) 98(9.4) 98(0.61) 98(2.6) 98(19) 98(31) 98(26) 98(30) 98(31) 98(27) 98(28) 98(33) 98(4.6) 98(7.7) 98(4.9) 98(1.6) 98(28) 98(30) 98(23) 98(13) 98(24) 98(28) 98(28) 98(15) 98(27) 98(27) 114(13)

111(81) 67(118) 67(180) 67(64) 67(193) 81(83) 81(84) 81(71) 43(49) 41(75) 55(92) 56(85) 56(93) 56(81) 56(81) 56(81) 69(83) 83(94) 41(57) 83(101) 41(71) 41(92) 56(117) 69(104) 56(75) 57(161) 41(116) 83(80) 83(97) 83(87) 83(89) 83(96) 83(105) 41(86) 56(105) 55(76) 41(98) 56(91) 69(113) 41(95) 69(118) 56(90) 69(86) 69(98) 69(97) 41(91) 55(64) 41(98) 43(226)

Three next most intense peaks 125(47) 39(44) 39(44) 68(50) 39(36) 68(38) 54(50) 67(52) 81(43) 81(70) 83(90) 70(77) 41(63) 70(78) 70(68) 55(63) 41(78) 55(78) 55(54) 55(83) 69(71) 69(86) 43(68) 41(85) 55(62) 41(86) 69(91) 55(75) 55(71) 55(82) 55(83) 55(92) 55(89) 69(80) 41(54) 41(60) 57(94) 41(75) 41(99) 69(90) 41(106) 55(74) 41(74) 41(82) 41(86) 56(79) 56(59) 56(65) 71(62)

45(22) 68(38) 41(30) 81(44) 41(35) 67(37) 39(44) 41(48) 27(39) 29(65) 41(69) 41(65) 55(61) 41(64) 41(63) 69(56) 68(60) 41(55) 56(50) 41(61) 55(62) 55(40) 41(61) 55(42) 43(55) 29(52) 27(43) 41(63) 41(52) 41(52) 41(52) 41(62) 41(58) 55(74) 27(30) 69(57) 56(80) 55(47) 27(36) 55(42) 55(40) 43(71) 55(62) 39(33) 55(63) 29(64) 41(50) 69(55) 27(49)

39(18) 54(35) 27(30) 54(30) 27(26) 39(33) 55(34) 39(35) 39(38) 27(47) 39(41) 55(65) 70(54) 55(59) 55(58) 41(55) 55(46) 42(34) 42(49) 39(33) 27(38) 39(35) 39(39) 27(36) 41(54) 55(49) 39(37) 39(34) 39(34) 27(32) 27(34) 39(35) 39(31) 27(33) 39(27) 56(48) 29(70) 27(42) 39(33) 27(36) 39(35) 41(57) 56(37) 27(33) 39(35) 55(54) 27(35) 55(47) 41(42)

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TABLE 7.76 Condensed Table of Mass Spectra (Continued) Mass numbers (and intensities) of: Molecular formula C 7H 14O2 C 7H 14O2 C 7H 14O2 C 7H 14O3 C 7H 14S C 7H 15N C 7H 16 C 7H 16 C 7H 16 C 7H 16 C 7H 16 C 7H 16 C 7H 16 C 7H 16 C 7H 16 C 7H 16O C 7H 16O C 7H 16O C 7H 16O C 7H 16O2 C 7H 16O2 C 7H 16O2 C 7H 16S C 7H 16S C 7H 16S C 7H 16S C 7H 18Pb C 7H 18Pb C 7H 18Pb C 7H 18Pb C 8H 10 C 8H 10 C 8H 10 C 8H 10 F3N HCl H 2S H 3P H 3N H 4N2 NO NO2 N2 N2O O2 O2S

Name n-Butyl propanoate Isobutyl propanoate n-Propyl n-butanoate n-Propyl carbonate cis-2-Methylcyclohexanethiol 2,6-Dimethylpiperidine 2,2,3-Trimethylbutane 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane 3-Ethylpentane 2-Methylhexane 3-Methylhexane n-Heptane 2-Heptanol 3-Heptanol 4-Heptanol n-Propyl n-butyl ether Di-n-propoxymethane Diisopropoxymethane 1,1-Diethoxypropane 2,2,4-Trimethyl-3-thiapentane 2,4-Dimethyl-3-thiahexane 2-Thiaoctane 1-Heptanethiol Methyltriethyllead n-Butyltrimethyllead sec-Butyltrimethyllead tert-Butyltrimethyllead 1,2-Dimethylbenzene 1,3-Dimethylbenzene 1,4-Dimethylbenzene Ethylbenzene Nitrogen trifluoride Hydrogen chloride Hydrogen sulfide Ammonia Phosphine Hydrazine Nitric oxide Nitrogen dioxide Nitrogen Nitrous oxide Oxygen Sulfur dioxide

Parent peak

Base peak

130(0.03) 130(0.07) 130(0.05) 146(0.02) 130(28) 113(5.3) 100(0.03) 100(0.06) 100(2.1) 100(1.6) 100(0.03) 100(3.1) 100(5.9) 100(4.0) 100(17) 116(0.01) 116(0.01) 116(0.02) 116(3.7) 132(0.58) 132(0.16) 132(0.0) 132(30) 132(30) 132(34) 132(14) 310(0.84) 310(0.14) 310(1.8) 310(0.09) 106(52) 106(58) 106(52) 106(45) 71(10) 36(54) 34(75) 17(32) 34(59) 32(48) 30(76) 46(6.6) 28(65) 44(60) 32(54) 64(47)

57(152) 57(187) 43(96) 43(171) 55(138) 98(73) 57(110) 57(130) 43(94) 43(139) 43(166) 43(175) 43(154) 43(110) 43(126) 45(131) 59(61) 55(102) 43(120) 43(194) 43(133) 59(138) 57(149) 61(94) 61(73) 41(48) 281(86) 253(76) 253(94) 252(95) 91(91) 91(93) 91(85) 91(146) 52(33) 36(54) 34(75) 17(32) 34(59) 32(48) 30(76) 30(18) 28(65) 44(60) 32(54) 64(47)

Three next most intense peaks 29(98) 29(87) 71(90) 27(61) 97(70) 44(43) 43(84) 43(95) 56(93) 57(93) 71(103) 70(77) 42(59) 57(52) 41(65) 43(29) 69(41) 73(72) 57(102) 73(114) 45(84) 47(88) 41(74) 103(60) 56(53) 27(40) 208(76) 223(75) 223(85) 223(82) 105(22) 105(26) 105(25) 51(19) 33(13) 38(17) 32(33) 16(26) 33(20) 31(23) 14(5.7) 16(4.0) 14(3.3) 30(19) 16(2.7) 48(23)

56(54) 56(27) 27(54) 63(55) 81(44) 42(34) 56(67) 41(59) 57(67) 41(59) 27(38) 70(77) 41(57) 71(52) 57(60) 27(25) 41(29) 43(45) 41(51) 27(45) 73(71) 87(84) 29(35) 41(51) 27(46) 56(39) 223(66) 208(68) 208(74) 208(65) 39(15) 39(17) 51(13) 39(14) 14(3.0) 35(9.2) 33(32) 15(2.4) 31(19) 29(19) 15(1.8) 14(1.7) 29(0.47) 14(7.8) 28(1.7) 32(4.9)

27(52) 27(47) 89(48) 41(49) 41(44) 28(26) 41(64) 56(52) 41(64) 56(50) 41(36) 29(45) 85(49) 41(50) 29(58) 29(23) 31(25) 27(32) 29(49) 41(34) 27(28) 29(74) 43(32) 43(46) 41(44) 70(38) 237(60) 295(52) 251(45) 250(46) 51(14) 51(14) 39(13) 65(12) 19(2.7) 37(2.9) 1(4.1) 14(0.7) 32(7.5) 30(15) 16(1.1) 47(0.02) ... 28(6.5) 34(0.22) 16(2.4)

Source: L. Meites, ed., Handbook of Analytical Chemistry, McGraw-Hill, New York, 1963. J. A. Dean, ed., Analytical Chemistry Handbook, McGraw-Hill, New York, 1995.

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ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM 8.1

ACTIVITY Table 8.1 Table 8.2 Table 8.3 Table 8.4

COEFFICIENTS Individual Activity Coefficients of Ions in Water at 25ⴗC Approximate Effective Ionic Radii in Aqueous Solutions at 25ⴗC Constants of the Debye-Hu¨ckel Equation from 0 to 100ⴗC Individual Ionic Activity Coefficients at Higher Ionic Strengths at 25ⴗC 8.2 EQUILIBRIUM CONSTANTS Table 8.5 Ionic Product Constant of Water Table 8.6 Solubility Product Constants 8.2.1 Proton-Transfer Reactions Table 8.7 Proton Transfer Reactions of Inorganic Materials in Water at 25ⴗC Table 8.8 pK a Values of Organic Materials in Water at 25ⴗC Table 8.9 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures Table 8.10 Properties of Common Acid-Base Solvents Table 8.11 pK a Values for Proton-Transfer Reactions in Nonaqueous Solvents 8.2.2 Formation Constants of Metal Complexes Table 8.12 Cumulative Formation Constants for Metal Complexes with Inorganic Ligands Table 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands 8.3 BUFFER SOLUTIONS 8.3.1 Standard Reference pH Buffer Solutions Table 8.14 National Bureau of Standards (U.S.) Reference pH Buffer Solutions Table 8.15 Compositions of Standard pH Buffer Solutions [National Bureau of Standards (U.S.)] 8.3.2 Standards for pH Measurement of Blood and Biological Media Table 8.16 Composition and pH Values of Buffer Solutions Table 8.17 Standard Reference Values pH* s for the Measurement of Acidity in 50 Weight Percent Methanol-Water Table 8.18 pH* Values for Buffer Solutions in Alcohol-Water Solvents at 25ⴗC 8.3.3 Buffer Solutions Other Than Standards Table 8.19 pH Values of Biological and Other Buffers for Control Purposes 8.4 REFERENCE ELECTRODES Table 8.20 Potentials of Reference Electrodes in Volts as a Function of Temperature Table 8.21 Potentials of Reference Electrodes (in Volts) at 25ⴗC for Water– Organic Solvent Mixtures 8.4.1 Electrometric Measurement of pH Table 8.22 Values of 2.3026RT/F at Several Temperatures 8.5 INDICATORS Table 8.23 Indicators for Aqueous Acid-Base Titrations Table 8.24 Mixed Indicators 8.1

8.2 8.3 8.4 8.5 8.5 8.6 8.6 8.6 8.17 8.18 8.24 8.73 8.80 8.81 8.82 8.83 8.88 8.104 8.104 8.105 8.106 8.106 8.107 8.109 8.109 8.110 8.110 8.113 8.113 8.114 8.115 8.115 8.116 8.116 8.118

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Table 8.25 Fluorescent Indicators Table 8.26 Selected List of Oxidation-Reduction Indicators 8.6 ELECTRODE POTENTIALS Table 8.27 Potentials of the Elements and Their Compounds at 25ⴗC Table 8.28 Potentials of Selected Half-Reactions at 25ⴗC Table 8.29 Overpotentials for Common Electrode Reactions at 25ⴗC Table 8.30 Half-Wave Potentials of Inorganic Materials Table 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25ⴗC 8.7 CONDUCTANCE Table 8.32 Limiting Equivalent Ionic Conductances in Aqueous Solutions Table 8.33 Standard Solutions for Calibrating Conductivity Vessels Table 8.34 Electrical Conductivity of Various Pure Liquids Table 8.35 Equivalent Conductivities of Electrolytes in Aqueous Solutions at 18ⴗC Table 8.36 Conductivity of Very Pure Water at Various Temperatures and the Equivalent Conductances of Hydrogen and Hydroxyl Ions 8.7.1 Common Conductance Relations

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8.120 8.122 8.124 8.124 8.137 8.140 8.141

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8.146 8.157 8.157 8.160 8.161 8.163 8.168 8.168

ACTIVITY COEFFICIENTS

Although it is not possible to measure an individual ionic activity coefficient, fi , it may be estimated from the following equation of the Debye-Hu¨ckel theory: ⫺log fi ⫽

Az 2i p I

1 ⫹ Ba˚p I

where I is the ionic strength of the medium, and a˚ is the ion-size parameter— the effective ionic radius (Table 8.2). The values of A and B vary with the temperature and dielectric constant of the solvent; values from 0 to 100⬚C for aqueous medium (a˚ in angstrom units) are listed in Table 8.3. Corresponding values of A and B for unit weight of solvent (when employing molality) can be obtained by multiplying the corresponding values for unit volume (molarity units) by the square root of the density of water at the appropriate temperature. The ionic strength can be estimated from the summation of the product molarity times ionic charge squared for all the ionic species present in the solution, i.e., I ⫽ 0.5(c1 z 21 ⫹ c2 z 22 ⫹ · · · ⫹ ci z 2i ). Values for the activity coefficients of ions in water at 25⬚C are given in Table 8.1 in terms of their effective ionic radii. At moderate ionic strengths a considerable improvement is effected by subtracting a term bI from the Debye-Hu¨ckel expression; b is an adjustable parameter which is 0.2 for water at 25⬚C. Table 8.4 ˚. gives the values of the ionic activity coefficients (for zi from 1 to 6) with a˚ taken to be 4.6A In general, the mean ionic activity coefficient is given by f⫾ ⫽ (x⫹y) p f ⫹x f ⫺y

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TABLE 8.1 Individual Activity Coefficients of Ions in Water at 25⬚C ƒi at Ionic Strength of Effective Ionic Radii ˚) a˚ (in A Univalent Ions 9 8 7 6 5 4 3.5 3 2.5 Divalent Ions 8 7 6 5 4.5 4 Trivalent Ions 6 5 4 Tetravalent Ions 11 5 Pentavalent Ions 9

0.001

0.005

0.01

0.05

0.1

0.967 0.966 0.965 0.965 0.964 0.964 0.964 0.964 0.964

0.933 0.931 0.930 0.929 0.928 0.928 0.926 0.925 0.924

0.914 0.912 0.909 0.907 0.904 0.902 0.900 0.899 0.898

0.86 0.85 0.845 0.835 0.83 0.82 0.81 0.805 0.80

0.83 0.82 0.81 0.80 0.79 0.775 0.76 0.755 0.75

0.872 0.872 0.870 0.868 0.868 0.867

0.755 0.755 0.749 0.744 0.741 0.740

0.69 0.685 0.675 0.67 0.663 0.660

0.52 0.50 0.485 0.465 0.45 0.445

0.45 0.425 0.405 0.38 0.36 0.355

0.731 0.728 0.725

0.52 0.51 0.505

0.415 0.405 0.395

0.195 0.18 0.16

0.13 0.115 0.095

0.588 0.57

0.35 0.31

0.255 0.20

0.10 0.048

0.065 0.021

0.43

0.18

0.105

0.020

0.009

where f⫹ , f⫺ are the individual ionic activity coefficients, and x,y are the charge numbers (z⫹ , z⫺ ) of the respective ions. In binary electrolyte solution. f⫾ ⫽ p f⫹ f⫺ In ternary electrolytes, e.g., BaCl2 or K2SO4 , 3 f⫾ ⫽ p f⫹ f ⫺2

or

3 2 f⫾ ⫽ p f ⫹ f⫺

In quaternary electrolytes, e.g., LaCl3 or K3[Fe(CN)6 ], 4 f⫾ ⫽ p f⫹ f ⫺3

or

4 3 f⫾ ⫽ p f ⫹ f⫺

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TABLE 8.2 Approximate Effective Ionic Radii in Aqueous Solutions at 25⬚C Inorganic Ions

2.5. . . . . . . . . . . . . . . . . . . 3. . . . . . . . . . . . . . . . . . . . . 3.5. . . . . . . . . . . . . . . . . . . 4. . . . . . . . . . . . . . . . . . . . .

Rb⫹, Cs⫹, NH⫹4 , Tl⫹, Ag ⫹ K ⫹, Cl⫺, Br ⫺, I ⫺, CN ⫺, NO⫺2 , NO3⫺ OH ⫺, F ⫺, SCN ⫺, OCN ⫺, HS⫺, ClO⫺3 , ClO4⫺ , BrO3⫺ , IO⫺4 , MnO⫺4 Na⫹, CdCl⫹, Hg 22⫹ , ClO2⫺ , IO3⫺ , HCO3⫺ , H2 PO4⫺ , HSO3 ⫺ , H 2 AsO⫺4 , SO24⫺, S 2O32⫺, S2 O82⫺ , SeO24⫺ , CrO24⫺ , HPO24⫺ , S 2O26⫺ , PO34⫺, Fe(CN)63⫺, Cr(NH 3 )36⫹, Co(NH 3 )63⫹ , Co(NH 3 )5 H 2O3⫹ Pb2⫹, CO23⫺, SO32⫺, MoO24⫺, Co(NH 3 )5Cl2⫹, Fe(CN)5NO2⫺ Sr 2⫹, Ba2⫹, Ra2⫹, Cd2⫹, Hg 2⫹, S2⫺, S2O24⫺, WO24⫺, Fe(CN)4⫺6 Li⫹, Ca2⫹, Cu2⫹, Zn2⫹, Sn2⫹, Mn2⫹, Fe 2⫹, Ni2⫹, Co 2⫹, Co(en)33⫹, Co(S2O3 )(CN)45⫺ Mg 2⫹, Be 2⫹ H ⫹, Al3⫹, Fe3⫹, Cr 3⫹, Sc 3⫹, Y 3⫹, La3⫹, In3⫹, Ce 3⫹, Pr 3⫹, Nd3⫹, Sm3⫹, Co(SO3)2(CN)54⫺ Th4⫹, Zr 4⫹, Ce 4⫹, Sn4⫹

4.5. . . . . . . . . . . . . . . . . . . 5. . . . . . . . . . . . . . . . . . . . . 6. . . . . . . . . . . . . . . . . . . . . 8. . . . . . . . . . . . . . . . . . . . . 9. . . . . . . . . . . . . . . . . . . . . 11 . . . . . . . . . . . . . . . . . . .

˚) a˚ (in A

Organic Ions

3.5. . . . . . . . . . . . . . . . . . . HCOO⫺, H 2Cit ⫺, CH3 NH3⫹, (CH 3)2 NH2⫹ 4. . . . . . . . . . . . . . . . . . . . . H 3 N ⫹CH 2COOH, (CH 3 )3 NH ⫹, C2 H5 NH⫹3 4.5. . . . . . . . . . . . . . . . . . . CH 3COO⫺, ClCH 2COO⫺, (CH 3 )4 N⫹, (C2 H5 )2 NH⫹2 , H 2 NCH 2COO⫺, oxalate 2⫺, HCit 2⫺ 5. . . . . . . . . . . . . . . . . . . . . Cl 2CHCOO⫺, Cl 3COO⫺, (C2 H 5 )3 NH ⫹, C3 H7 NH⫹3 , Cit 3⫺, succinate 2⫺, malonate 2⫺, tartrate2⫺ 6. . . . . . . . . . . . . . . . . . . . . benzoate ⫺, hydroxybenzoate ⫺, chlorobenzoate ⫺, phenylacetate ⫺, vinylacetate ⫺, (CH 3 )2C " CHCOO⫺, (C2 H 5 )4N ⫹, ⫹ 2⫺ 2⫺ 2⫺ (C3 H 7 )2 NH 2 , phthalate , glutarate , adipate 7. . . . . . . . . . . . . . . . . . . . . trinitrophenolate ⫺, (C3 H 7 )3 NH ⫹, methoxybenzoate⫺, pimelate2⫺, suberate2⫺, Congo red anion2⫺ 8. . . . . . . . . . . . . . . . . . . . . (C6 H 5 )2CHCOO⫺, (C3 H 7 )4 N ⫹

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TABLE 8.3 Constants of the Debye-Hu¨ckel Equation from 0 to 100⬚C ⫺log ƒi ⫽

Az 2i p I

1 ⫹ Ba˚p I Unit Volume of Solvent

Unit Volume of Solvent Temp., ⬚C

A

B

0 5 10 15 20 25 30 35 40 45 50

0.4918 0.4952 0.4989 0.5028 0.5070 0.5115 0.5161 0.5211 0.5262 0.5317 0.5373

0.3248 0.3256 0.3264 0.3273 0.3282 0.3291 0.3301 0.3312 0.3323 0.3334 0.3346

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A

B

55 60 65 70 75 80 85 90 95 100

0.5432 0.5494 0.5558 0.5625 0.5695 0.5767 0.5842 0.5920 0.6001 0.6086

0.3358 0.3371 0.3384 0.3397 0.3411 0.3426 0.3440 0.3456 0.3471 0.3488

The values for unit weight of solvent (molality scale) can be obtained by multiplying the corresponding values for unit volume by the square root of the density of water at the appropriate temperature.

TABLE 8.4 Individual Ionic Activity Coefficients at Higher Ionic Strengths at 25⬚C The values were calculated from the modified Debye-Hu¨ckel equation utilizing the modifications proposed by Robinson and by Guggenheim and Bates: ⫺

log ƒi 0.511I ⫽ ⫺ 0.2I z 2i 1 ⫹ 1.5I

˚. where I is the ionic strength and a˚ is assumed to be 4.6 A

I

0.05 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0

⫺

log10 ƒi z 2i

0.0756 0.0896 0.0968 0.0936 0.0858 0.0753 0.0631 0.0496 0.0352 0.0201 0.0044

ƒi for z i ⫽ 1

2

3

4

5

6

0.840 0.814 0.800 0.806 0.821 0.841 0.865 0.892 0.922 0.955 0.900

0.498 0.438 0.410 0.422 0.454 0.500 0.559 0.633 0.723 0.831 0.960

0.209 0.156 0.138 0.144 0.169 0.210 0.2705 0.358 0.482 0.659 0.913

0.0617 0.0369 0.0283 0.0318 0.0424 0.0624 0.0978 0.161 0.273 0.477 0.850

0.0129 0.00576 0.00380 0.00457 0.00716 0.0131 0.0265 0.05755 0.132 0.314 0.776

0.00190 0.000595 0.000328 0.000427 0.000815 0.00195 0.00535 0.0164 0.0541 0.189 0.694

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EQUILIBRIUM CONSTANTS

TABLE 8.5 Ionic Product Constant of Water This table gives values of pKw on a molal scale, where Kw is the ionic activity product constant of water. Values are from W. L. Marshall and E. U. Franck, J. Phys. Chem. Ref. Data, 10:295 (1981). Temp., ⬚C

pKw

Temp., ⬚C

pKw

Temp., ⬚C

pKw

0 5 10 15 18 20 25 30 35 40

14.938 14.727 14.528 14.340 14.233 14.163 13.995 13.836 13.685 13.542

45 50 55 60 65 70 75 80 85 90

13.405 13.275 13.152 13.034 12.921 12.814 12.711 12.613 12.520 12.431

95 100 125 150 175 200 225 250 275 300

12.345 12.264 11.911 11.637 11.431 11.288 11.207 11.192 11.251 11.406

TABLE 8.6 Solubility Product Constants The data refer to various temperatures between 18 and 25⬚C, and were compiled from values cited by Bjerrum, Schwarzenbach, and Sillen, Stability Constants of Metal Complexes, part II, Chemical Society, London, 1958, and values taken from publications of the IUPAC Solubility Data Project: Solubility Data Series, International Union of Pure and Applied Chemistry, Pergamon Press, Oxford, 1979– 1992; H. L. Clever, and F. J. Johnston, J. Phys. Chem. Ref. Data, 9:751 (1980); Y. Marcus, Ibid. 9:1307 (1980); H. L. Clever, S. A. Johnson, and M. E. Derrick, Ibid. 14:631 (1985), and 21:941 (1992). In the table, “L” is the abbreviation of the organic ligand. Compound Actinium hydroxide Aluminum arsonate cupferrate hydroxide phosphate 8-quinolinolate selenide sulfide Americium (III) hydroxide (IV) hydroxide Ammonium uranyl arsenate Arsenic (III) sulfide

Formula

pKsp

Ksp 1 ⫻ 10⫺15

Ac(OH)3

15

AlAsO4 AlL 3 Al(OH)3 AlPO4 AlL 3 Al 2Se 3 Al 2S3

15.80 18.64 32.89 20.01 29.00 24.4 6.7

Am(OH)3 Am(OH)4

19.57 56

2.7 ⫻ 10⫺20 1 ⫻ 10⫺56

NH 4UO2 AsO4

23.77

1.7 ⫻ 10⫺24

As 2S3

21.68

2.1 ⫻ 10⫺22

1.6 2.3 1.3 9.84 1.00 4 2

⫻ 10⫺16 ⫻ 10⫺19 ⫻ 10⫺33 ⫻ 10⫺21 ⫻ 10⫺29 ⫻ 10⫺25 ⫻ 10⫺7

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TABLE 8.6 Solubility Product Constants (Continued) Compound Barium arsenate bromate carbonate chromate ferricyanide 6-hydrate fluoride hexafluorosilicate hydrogen phosphate hydroxide 8-hydrate iodate hydrate molybdate niobate nitrate oxalate oxalate hydrate permanganate perrhenate phosphate pyrophosphate 8-quinolinolate selenate sulfate sulfite thiosulfate Beryllium carbonate 4-hydrate hydroxide (amorphous) molybdate niobate Bismuth arsenate cupferrate hydroxide iodide oxide bromide oxide chloride oxide hydroxide oxide nitrate oxide nitrite oxide thiocyanate phosphate sulfide Cadmium anthranilate arsenate benzoate 2-hydrate borate, meta carbonate cyanide ferrocyanide fluoride

Formula

top of rh base of rh

pKsp

Ksp

Ba 3(AsO4 )2 Ba(BrO3 )2 BaCO3 BaCrO4 Ba 2 [Fe(CN)6 ] · 6H 2O BaF2 BaSiF6 BaHPO4 Ba(OH)2 · 8H 2O Ba(IO3 )2 · H 2O BaMoO4 Ba(NbO3 )2 Ba(NO3 )2 BaC 2O4 BaC 2O4 · H 2O Ba(MnO4 )2 Ba(ReO4 )2 Ba 3(PO4 )2 Ba 2 P2O7 BaL 2 BaSeO4 BaSO4 BaSO3 BaS2O3

50.11 5.50 8.59 9.93 7.49 6.74 6 6.49 3.59 8.40 7.45 16.50 2.33 6.79 7.64 9.61 1.28 22.47 10.50 8.30 7.47 9.97 9.30 4.79

8.0 2.43 2.58 1.17 3.2 1.84 1 3.2 2.55 4.01 3.54 3.2 4.64 1.6 2.3 2.5 5.2 3.4 3.2 5.0 3.40 1.08 5.0 1.6

⫻ 10⫺51 ⫻ 10⫺4 ⫻ 10⫺9 ⫻ 10⫺10 ⫻ 10⫺8 ⫻ 10⫺7 ⫻ 10⫺6 ⫻ 10⫺7 ⫻ 10⫺4 ⫻ 10⫺9 ⫻ 10⫺8 ⫻ 10⫺17 ⫻ 10⫺3 ⫻ 10⫺7 ⫻ 10⫺8 ⫻ 10⫺10 ⫻ 10⫺2 ⫻ 10⫺23 ⫻ 10⫺11 ⫻ 10⫺9 ⫻ 10⫺8 ⫻ 10⫺10 ⫻ 10⫺10 ⫻ 10⫺5

BeCO3 · 4H 2O Be(OH)2 BeMoO4 Be(NbO3 )2

3 21.16 1.49 15.92

1 6.92 3.2 1.2

⫻ 10⫺3 ⫻ 10⫺22 ⫻ 10⫺2 ⫻ 10⫺16

BiAsO4 BiL 3 Bi(OH)3 BiI 3 BiOBr BiOCl BiO(OH) BiO(NO3 ) BiO(NO2 ) BiO(SCN) BiPO4 Bi 2S3

9.35 27.22 30.4 18.11 6.52 30.75 9.4 2.55 6.31 6.80 22.89 97

4.43 6.0 6.0 7.71 3.0 1.8 4 2.82 4.9 1.6 1.3 1

⫻ 10⫺10 ⫻ 10⫺28 ⫻ 10⫺31 ⫻ 10⫺19 ⫻ 10⫺7 ⫻ 10⫺31 ⫻ 10⫺10 ⫻ 10⫺3 ⫻ 10⫺7 ⫻ 10⫺7 ⫻ 10⫺23 ⫻ 10⫺97

CdL 2 Cd 3(AsO4 )2 CdL 2 · 2H 2O Cd(BO2 )2 CdCO3 Cd(CN)2 Cd 2 [Fe(CN)6 ] CdF2

8.27 32.66 2.7 8.64 12.0 8.0 16.49 2.19

5.4 2.2 2 2.3 1.0 1.0 3.2 6.44

⫻ 10⫺9 ⫻ 10⫺33 ⫻ 10⫺3 ⫻ 10⫺9 ⫻ 10⫺12 ⫻ 10⫺8 ⫻ 10⫺17 ⫻ 10⫺3

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TABLE 8.6 Solubility Product Constants (Continued) Compound hydroxide iodate oxalate 3-water phosphate quinaldate sulfide tungstate Calcium acetate 3-water arsenate benzoate 3-water carbonate carbonate (calcite) carbonate (aragonite) carbonatomagnesium chromate fluoride hexafluorosilicate hydrogen phosphate hydroxide iodate 6-water molybdate niobate oxalate hydrate phosphate 8-quinolinolate selenate selenite silicate, meta sulfate sulfate dihydrate sulfite sulfite 0.5-water tartrate dihydrate tungstate Cerium (III) fluoride (III) hydroxide (IV) hydroxide (III) iodate (IV) iodate (III) oxalate 9-water (III) phosphate (III) selenite (III) sulfide (III) tartrate Cesium bromate chlorate cobaltihexanitrite hexachloroplatinate(IV) hexafluoroplatinate(IV) hexafluorosilicate

Formula

pKsp

Ksp

Cd(OH)2 fresh Cd(IO3 )2 CdC 2O4 · 3H 2O Cd 3(PO4 )2 CdL 2 CdS CdWO4

14.14 7.60 7.85 32.60 12.30 26.10 5.7

7.2 2.5 1.42 2.53 5.0 8.0 2

⫻ 10⫺15 ⫻ 10⫺8 ⫻ 10⫺8 ⫻ 10⫺33 ⫻ 10⫺13 ⫻ 10⫺27 ⫻ 10⫺6

Ca(OAc)2 · 3H 2O Ca 3(AsO4 )2 CaL 2 · 3H 2O CaCO3 CaCO3 CaCO3 Ca[Mg(CO3 )2 ] dolomite CaCrO4 CaF2 Ca[SiF6 ] CaHPO4 Ca(OH)2 Ca(IO3 )2 · 6H 2O CaMoO4 Ca(NbO3 )2 CaC 2O4 · H 2O Ca 3(PO4 )2 CaL 2 CaSeO4 CaSeO3 CaSiO3 CaSO4 CaSO4 · 2H 2O CaSO3 CaSO3 · 0.5H 2O CaL · 2H 2O CaWO4

2.4 18.17 2.4 8.54 8.47 8.22 11 3.15 8.28 3.09 7.0 5.26 6.15 7.84 17.06 8.63 28.68 11.12 3.09 5.53 7.60 4.31 4.50 7.17 6.51 6.11 8.06

4 6.8 4 2.8 3.36 6.0 1 7.1 5.3 8.1 1.0 5.5 7.10 1.46 8.7 2.32 2.07 7.6 8.1 8.0 2.5 4.93 3.14 6.8 3.1 7.7 8.7

⫻ 10⫺3 ⫻ 10⫺19 ⫻ 10⫺3 ⫻ 10⫺9 ⫻ 10⫺9 ⫻ 10⫺9 ⫻ 10⫺11 ⫻ 10⫺4 ⫻ 10⫺9 ⫻ 10⫺4 ⫻ 10⫺7 ⫻ 10⫺6 ⫻ 10⫺7 ⫻ 10⫺8 ⫻ 10⫺18 ⫻ 10⫺9 ⫻ 10⫺29 ⫻ 10⫺12 ⫻ 10⫺4 ⫻ 10⫺6 ⫻ 10⫺8 ⫻ 10⫺5 ⫻ 10⫺5 ⫻ 10⫺8 ⫻ 10⫺7 ⫻ 10⫺7 ⫻ 10⫺9

CeF3 Ce(OH)3 Ce(OH)4 Ce(IO3 )3 Ce(IO3 )4 Ce 2(C 2O4 )3 · 9H 2O CePO4 Ce 2(SeO3 )3 Ce 2S3 Ce 2 L 3

15.1 19.80 47.7 9.50 16.3 25.50 23 24.43 10.22 19.0

8 1.6 2 3.2 5 3.2 1 3.7 6.0 1.0

⫻ 10⫺16 ⫻ 10⫺20 ⫻ 10⫺48 ⫻ 10⫺10 ⫻ 10⫺17 ⫻ 10⫺26 ⫻ 10⫺23 ⫻ 10⫺25 ⫻ 10⫺11 ⫻ 10⫺19

CsBrO3 CsClO3 Cs 3 [Co(NO2 )6 ] Cs 2 [PtCl 6 ] Cs 2 [PtF6 ] Cs 2 [SiF6 ]

1.7 1.4 15.24 7.50 5.62 4.90

5 4 5.7 3.2 2.4 1.3

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TABLE 8.6 Solubility Product Constants (Continued) Compound perchlorate periodate permanganate perrhanate tetrafluoroborate Chromium(II) hydroxide Chromium(III) arsenate fluoride hydroxide phosphate 4-water Cobalt anthranilate arsenate carbonate ferrocyanide hydrogen phosphate (II) hydroxide (III) hydroxide iodate phosphate selenite quinaldate 8-quinolinolate sulfide Copper(I) azide bromide chloride cyanide hydroxide iodide sulfide tetraphenylborate thiocyanate Copper(II) anthranilate arsenate azide carbonate chromate dithiooxamide ferrocyanide hydroxide iodate oxalate phosphate pyrophosphate quinaldate 8-quinolinolate

Formula CsClO4 CsIO4 CsMnO4 CsReO4 Cs[BF4 ]

top of rh base of rh

pKsp 2.40 5.29 4.08 3.40 4.7

Ksp 3.95 5.16 8.2 4.0 5

⫻ 10⫺3 ⫻ 10⫺6 ⫻ 10⫺5 ⫻ 10⫺4 ⫻ 10⫺5

2 ⫻ 10⫺16

Cr(OH)2

15.7

CrAsO4 CrF3 Cr(OH)3 CrPO4 · 4H 2O green violet

20.11 10.18 30.20 22.62 17.00

7.7 6.6 6.3 2.4 1.0

⫻ 10⫺21 ⫻ 10⫺11 ⫻ 10⫺31 ⫻ 10⫺23 ⫻ 10⫺17

CoL 2 Co3(AsO4 )2 CoCO3 Co2 [Fe(CN)6 ] CoHPO4 Co(OH)2 fresh Co(OH)3 Co(IO3 )2 Co3 (PO4 )2 CoSeO3 CoL 2 CoL 2 ␣-CoS ␤-CoS

9.68 28.17 12.84 14.74 6.7 14.23 43.80 4.0 34.69 6.80 10.80 24.80 20.40 24.70

2.1 6.80 1.4 1.8 2 5.92 1.6 1.0 2.05 1.6 1.6 1.6 4.0 2.0

⫻ 10⫺10 ⫻ 10⫺29 ⫻ 10⫺13 ⫻ 10⫺15 ⫻ 10⫺7 ⫻ 10⫺15 ⫻ 10⫺44 ⫻ 10⫺4 ⫻ 10⫺35 ⫻ 10⫺7 ⫻ 10⫺11 ⫻ 10⫺25 ⫻ 10⫺21 ⫻ 10⫺25

CuN 3 CuBr CuCl CuCN CuOH CuI Cu2S CuL CuSCN

8.31 8.20 6.76 19.46 14 11.90 47.60 8.0 12.75

4.9 6.27 1.72 3.47 1 1.27 2.5 1.0 1.77

⫻ 10⫺9 ⫻ 10⫺9 ⫻ 10⫺7 ⫻ 10⫺20 ⫻ 10⫺14 ⫻ 10⫺12 ⫻ 10⫺48 ⫻ 10⫺8 ⫻ 10⫺13

CuL 2 Cu 3 (AsO4 )2 Cu(N3 )2 CuCO3 CuCrO4 CuL Cu 2 [Fe(CN)6 ] Cu(OH)2 Cu(IO3 )2 CuC 2O4 Cu 3 (PO4 )2 Cu 2 P2O7 CuL 2 CuL 2

13.22 35.10 9.20 9.86 5.44 15.12 15.89 19.66 7.16 9.35 36.85 15.08 16.80 29.70

6.0 7.95 6.3 1.4 3.6 7.67 1.3 2.2 6.94 4.43 1.40 8.3 1.6 2.0

⫻ 10⫺14 ⫻ 10⫺36 ⫻ 10⫺10 ⫻ 10⫺10 ⫻ 10⫺6 ⫻ 10⫺16 ⫻ 10⫺16 ⫻ 10⫺20 ⫻ 10⫺8 ⫻ 10⫺10 ⫻ 10⫺37 ⫻ 10⫺16 ⫻ 10⫺17 ⫻ 10⫺30

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TABLE 8.6 Solubility Product Constants (Continued) Compound selenite sulfide Dysprosium chromate 10-water hydroxide Erbium hydroxide Europium hydroxide Gadolinium hydrogen carbonate hydroxide Gallium ferrocyanide hydroxide 8-quinolinolate Germanium oxide Gold(I) chloride iodide Gold(III) chloride hydroxide iodide oxalate Hafnium hydroxide Holmium hydroxide Indium ferrocyanide hydroxide quinolinolate selenite sulfide Iron(II) carbonate fluoride hydroxide oxalate dihydrate sulfide Iron(III) arsenate ferrocyanide hydroxide phosphate dihydrate quinaldate selenite Lanthanum bromate 9-water fluoride

Formula

pKsp

Ksp

CuSeO3 CuS

7.68 35.20

2.1 ⫻ 10⫺8 6.3 ⫻ 10⫺36

Dy2 (CrO4 )3 · 10H 2O Dy(OH)3

8 21.85

1 ⫻ 10⫺8 1.4 ⫻ 10⫺22

Er(OH)3

23.39

4.1 ⫻ 10⫺24

Eu(OH)3

23.03

9.38 ⫻ 10⫺24

Gd(HCO3 )3 Gd(OH)3

1.7 22.74

2 ⫻ 10⫺2 1.8 ⫻ 10⫺23

Ga 4 [Fe(CN)6 ]3 Ga(OH)3 GaL 3

33.82 35.14 40.80

1.5 ⫻ 10⫺34 7.28 ⫻ 10⫺36 1.6 ⫻ 10⫺41

GeO2

57.0

1.0 ⫻ 10⫺57

AuCl AuI

12.70 22.80

2.0 ⫻ 10⫺13 1.6 ⫻ 10⫺23

AuCl 3 Au(OH)3 AuI 3 Au 2 (C 2O4 )3

24.50 45.26 46 10

3.2 5.5 1 1

Hf(OH)3

25.40

4.0 ⫻ 10⫺26

Ho(OH)3

22.3

5.0 ⫻ 10⫺23

In 4 [Fe(CN)6 ]3 In(OH)3 InL 3 In 2 (SeO3 )3 In 2S3

43.72 33.2 31.34 32.60 73.24

1.9 6.3 4.6 4.0 5.7

⫻ 10⫺44 ⫻ 10⫺34 ⫻ 10⫺32 ⫻ 10⫺33 ⫻ 10⫺74

FeCO3 FeF2 Fe(OH)2 FeC 2O4 · 2H 2O FeS

10.50 5.63 16.31 6.50 17.20

3.13 2.36 4.87 3.2 6.3

⫻ 10⫺11 ⫻ 10⫺6 ⫻ 10⫺17 ⫻ 10⫺7 ⫻ 10⫺18

FeAsO4 Fe 4 [Fe(CN)6 ]3 Fe(OH)3 FePO4 · 2H 2O FeL 3 Fe 2 (SeO3 )3

20.24 40.52 38.55 15.00 16.89 30.70

5.7 3.3 2.79 9.91 1.3 2.0

⫻ 10⫺21 ⫻ 10⫺41 ⫻ 10⫺39 ⫻ 10⫺16 ⫻ 10⫺17 ⫻ 10⫺31

La(BrO3 )3 · 9H 2O LaF3

2.50 16.2

⫻ 10⫺25 ⫻ 10⫺46 ⫻ 10⫺46 ⫻ 10⫺10

3.2 ⫻ 10⫺3 7 ⫻ 10⫺17

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TABLE 8.6 Solubility Product Constants (Continued) Compound hydroxide iodate molybdate oxalate 9-water phosphate sulfide tungstate trihydrate Lead acetate anthranilate arsenate azide borate, meta bromate bromide carbonate chloride chloride fluoride chlorite chromate ferrocyanide fluoride fluoride iodide hydrogen phosphate hydrogen phosphite hydroxide hydroxide bromide hydroxide chloride hydroxide nitrate iodate iodide molybdate niobate oxalate phosphate quinaldate selenate selenite sulfate sulfide thiocyanate thiosulfate tungstate Lead(IV) hydroxide Lithium carbonate fluoride phosphate uranylarsenate Lutetium hydroxide

Formula

top of rh base of rh

pKsp

Ksp

La(OH)3 La(IO3 )3 La 2 (MoO4 )3 La 2 (C 2O4 )3 LaPO4 La 2S3 La 2 (WO4 )3 · 3H 2O

18.70 11.12 20.4 26.60 22.43 12.70 3.90

2.0 7.50 4 2.5 3.7 2.0 1.3

⫻ 10⫺19 ⫻ 10⫺12 ⫻ 10⫺21 ⫻ 10⫺27 ⫻ 10⫺23 ⫻ 10⫺13 ⫻ 10⫺4

Pb(OAc)2 PbL 2 Pb3 (AsO4 )3 Pb(N 3 )2 Pb(BO2 )3 Pb(BrO3 )2 PbBr2 PbCO3 PbCl 2 PbClF Pb(ClO2 )2 PbCrO4 Pb2 [Fe(CN)6 ] PbF2 PbFI PbHPO4 PbHPO3 Pb(OH)2 PbOHBr PbOHCl PbOHNO3 Pb(IO3 )2 PbI 2 PbMoO4 Pb(NbO3 )2 PbC 2O4 Pb3 (PO4 )2 PbL 2 PbSeO4 PbSeO3 PbSO4 PbS Pb(SCN)2 PbS2O3 PbWO4

2.75 9.81 35.39 8.59 10.78 1.70 6.82 13.13 4.77 8.62 8.4 12.55 14.46 7.48 8.07 9.90 6.24 14.84 14.70 13.7 3.55 12.43 8.01 13.00 16.62 9.32 42.10 10.60 6.84 11.50 7.60 27.10 4.70 6.40 6.35

1.8 1.6 4.0 2.5 1.6 2.0 6.60 7.4 1.70 2.4 4 2.8 3.5 3.3 8.5 1.3 5.8 1.43 2.0 2 2.8 3.69 9.8 1.0 2.4 4.8 8.0 2.5 1.37 3.2 2.53 8.0 2.0 4.0 4.5

⫻ 10⫺3 ⫻ 10⫺10 ⫻ 10⫺36 ⫻ 10⫺9 ⫻ 10⫺11 ⫻ 10⫺2 ⫻ 10⫺6 ⫻ 10⫺14 ⫻ 10⫺5 ⫻ 10⫺9 ⫻ 10⫺9 ⫻ 10⫺13 ⫻ 10⫺15 ⫻ 10⫺8 ⫻ 10⫺9 ⫻ 10⫺10 ⫻ 10⫺7 ⫻ 10⫺15 ⫻ 10⫺15 ⫻ 10⫺14 ⫻ 10⫺4 ⫻ 10⫺13 ⫻ 10⫺9 ⫻ 10⫺13 ⫻ 10⫺17 ⫻ 10⫺10 ⫻ 10⫺43 ⫻ 10⫺11 ⫻ 10⫺7 ⫻ 10⫺12 ⫻ 10⫺8 ⫻ 10⫺28 ⫻ 10⫺5 ⫻ 10⫺7 ⫻ 10⫺7

Pb(OH)4

65.50

Li 2CO3 LiF Li 3 PO4 LiUO2 AsO4

1.60 2.74 10.63 18.82

Lu(OH)3

23.72

3.2 ⫻ 10⫺66 2.5 1.84 2.37 1.5

⫻ 10⫺2 ⫻ 10⫺3 ⫻ 10⫺11 ⫻ 10⫺19

1.9 ⫻ 10⫺24

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TABLE 8.6 Solubility Product Constants (Continued) Compound Magnesium ammonium phosphate arsenate carbonate carbonate trihydrate fluoride hydroxide iodate 4-water niobate oxalate dihydrate phosphate 8-quinolinolate selenite sulfite Manganese anthranilate arsenate carbonate ferrocyanide iodate hydroxide oxalate dihydrate 8-quinolinolate selenite sulfide Mercury(I) azide bromide carbonate chloride cyanide chromate ferricyanide fluoride hydrogen phosphate hydroxide iodate iodide oxalate quinaldate selenite sulfate sulfite sulfide thiocyanate tungstate Mercury(II) bromide hydroxide iodate iodide 1,10-phenanthroline

Formula

pKsp

Ksp

MgNH 4 PO4 Mg3(AsO4 )2 MgCO3 MgCO3 · 3H 2O MgF2 Mg(OH)2 Mg(IO3 )2 · 4H 2O Mg(NbO3 )2 MgC 2O4 · 2H 2O Mg3 (PO4 )2 MgL 2 MgSeO3 MgSO3

12.60 19.68 5.17 5.62 10.29 11.25 2.50 16.64 5.32 23.98 15.40 4.89 2.50

2.5 2.1 6.82 2.38 5.16 5.61 3.2 2.3 4.83 1.04 4.0 1.3 3.2

⫻ 10⫺13 ⫻ 10⫺20 ⫻ 10⫺6 ⫻ 10⫺6 ⫻ 10⫺11 ⫻ 10⫺12 ⫻ 10⫺3 ⫻ 10⫺17 ⫻ 10⫺6 ⫻ 10⫺24 ⫻ 10⫺16 ⫻ 10⫺5 ⫻ 10⫺3

MnL 2 Mn 3 (AsO4 )2 MnCO3 Mn 2 [Fe(CN)6 ] Mn(IO3 )2 Mn(OH)2 MnC 2O4 · 2H 2O MnL 2 MnSeO3 MnS amorphous MnS crystalline

6.75 28.72 10.63 12.10 6.36 12.72 6.77 21.70 6.90 9.60 12.60

1.8 1.9 2.34 8.0 4.37 1.9 1.70 2.0 1.3 2.5 2.5

⫻ 10⫺3 ⫻ 10⫺29 ⫻ 10⫺11 ⫻ 10⫺13 ⫻ 10⫺7 ⫻ 10⫺13 ⫻ 10⫺7 ⫻ 10⫺22 ⫻ 10⫺7 ⫻ 10⫺10 ⫻ 10⫺13

Hg2 (N 3 )2 Hg2 Br2 Hg2CO3 Hg2Cl 2 Hg2 (CN)2 Hg2CrO4 (Hg2 )3 [Fe(CN)6 ]2 Hg2 F2 Hg2 HPO4 Hg2 (OH)2 Hg2 (IO3 )2 Hg2 I 2 Hg2C2O4 Hg2 L 2 Hg2SeO3 Hg2SO4 Hg2SO3 Hg 2S Hg2 (SCN)2 Hg2WO4

9.15 22.19 16.44 17.84 39.3 8.70 20.07 5.51 12.40 23.70 13.71 28.72 12.76 17.90 14.20 6.19 27.0 47.0 19.49 16.96

7.1 6.40 3.6 1.43 5 2.0 8.5 3.10 4.0 2.0 2.0 5.2 1.75 1.3 8.4 6.5 1.0 1.0 3.2 1.1

⫻ 10⫺10 ⫻ 10⫺23 ⫻ 10⫺17 ⫻ 10⫺18 ⫻ 10⫺40 ⫻ 10⫺9 ⫻ 10⫺21 ⫻ 10⫺6 ⫻ 10⫺13 ⫻ 10⫺24 ⫻ 10⫺14 ⫻ 10⫺29 ⫻ 10⫺13 ⫻ 10⫺18 ⫻ 10⫺15 ⫻ 10⫺7 ⫻ 10⫺27 ⫻ 10⫺47 ⫻ 10⫺20 ⫻ 10⫺17

HgBr2 Hg(OH)2 Hg(IO3 )2 HgI 2 HgL 2

19.21 25.52 12.49 28.54 24.70

6.2 3.2 3.2 2.9 2.0

⫻ 10⫺20 ⫻ 10⫺26 ⫻ 10⫺13 ⫻ 10⫺29 ⫻ 10⫺25

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TABLE 8.6 Solubility Product Constants (Continued) Compound quinaldate selenite sulfide Neodymium carbonate hydroxide Neptunyl(VI) hydroxide Nickel ammine perrhenate anthranilate arsenate carbonate ferrocyanide hydrazine sulfate hydroxide iodate oxalate phosphate pyrophosphate quinaldate 8-quinolinolate selenite ␣-sulfide ␤-sulfide ␥-sulfide Palladium (II) hydroxide (IV) hydroxide quinaldate thiocyanate Platinum (IV) bromide (II) hydroxide Plutonium (III) fluoride (IV) fluoride (IV) hydrogen phosphate (III) hydroxide (IV) hydroxide (IV) iodate (VI) carbonate (V) hydroxide (VI) hydroxide Polonium sulfide Potassium hexabromoplatinate hexachloropalladinate hexachloroplatinate hexafluoroplatinate

Formula

pKsp

Ksp

16.80 13.82 52.4 51.80

Nd 2 (CO3 )3 Nd(OH)3

32.97 21.49

1.08 ⫻ 10⫺33 3.2 ⫻ 10⫺22

NpO2 (OH)2

21.60

2.5 ⫻ 10⫺22

[Ni(NH 3 )6 ][ReO4 ]2 NiL 2 Ni 3 (AsO4 )2 NiCO3 Ni 2 [Fe(CN)6 ] [Ni(N 2 H 4 )3 ]SO4 Ni(OH)2 fresh Ni(IO3 )2 NiC 2O4 Ni 3 (PO4 )2 Ni 2 P2O7 NiL 2 NiL 2 NiSeO3 ␣-NiS ␤-NiS ␥-NiS

3.29 9.09 25.51 6.85 14.89 13.15 15.26 4.33 9.4 31.32 12.77 10.1 26.1 5.0 18.50 24.0 25.70

5.1 8.1 3.1 1.42 1.3 7.1 5.48 4.71 4 4.74 1.7 8 8 1.0 3.2 1.0 2.0

⫻ 10⫺4 ⫻ 10⫺10 ⫻ 10⫺26 ⫻ 10⫺7 ⫻ 10⫺15 ⫻ 10⫺15 ⫻ 10⫺16 ⫻ 10⫺5 ⫻ 10⫺10 ⫻ 10⫺32 ⫻ 10⫺13 ⫻ 10⫺11 ⫻ 10⫺27 ⫻ 10⫺5 ⫻ 10⫺19 ⫻ 10⫺24 ⫻ 10⫺26

Pd(OH)2 Pd(OH)4 PdL 2 Pd(SCN)2

31.0 70.20 12.90 22.36

1.0 6.3 1.3 4.39

⫻ 10⫺31 ⫻ 10⫺71 ⫻ 10⫺13 ⫻ 10⫺23

PtBr4 Pt(OH)2

40.50 35

3.2 ⫻ 10⫺41 1 ⫻ 10⫺35

PuF3 PuF4 Pu(HPO4 )2 · xH 2O Pu(OH)3 Pu(OH)4 Pu(IO3 )4 PuO2CO3 PuO2 (OH) PuO2 (OH)2

15.60 19.20 27.7 19.70 55 12.3 12.77 9.3 24.7

2.5 6.3 2 2.0 1 5 1.7 5 2

PoS

28.26

5.6 ⫻ 10⫺29

4.20 5.22 5.13 4.54

1.6 1.5 4 1.6

⫻ 10⫺17 ⫻ 10⫺14 ⫻ 10⫺53 ⫻ 10⫺52

HgL 2 HgSeO3 HgS red HgS black

K 2 [PtBr6 ] K 2 [PdCl 6 ] K 2 [PtCl 6 ] K 2 [PtF6 ]

top of rh base of rh

6.3 6.0 7.48 2.9

⫻ 10⫺16 ⫻ 10⫺20 ⫻ 10⫺28 ⫻ 10⫺20 ⫻ 10⫺55 ⫻ 10⫺13 ⫻ 10⫺13 ⫻ 10⫺10 ⫻ 10⫺25

⫻ 10⫺5 ⫻ 10⫺6 ⫻ 10⫺6 ⫻ 10⫺5

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8.14

INTERACTIVE

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SECTION 8

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TABLE 8.6 Solubility Product Constants (Continued) Compound hexafluorosilicate hexafluorozirconate iodate perchlorate sodium cobaltinitrite hydrate tetraphenylborate uranyl arsenate uranyl carbonate Praseodymium hydroxide Promethium hydroxide Radium iodate sulfate Rhodium hydroxide Rubidium cobaltinitrite hexachloroplatinate hexafluoroplatinate hexafluorosilicate perchlorate periodate Ruthenium hydroxide Samarium hydroxide Scandium fluoride hydroxide Silver acetate arsenate azide bromate bromide carbonate chloride chlorite chromate cobaltinitrite cyanamide cyanate cyanide dichromate dicyanimide ferrocyanide hydroxide hyponitrite iodate

Formula

pKsp

Ksp 8.7 5 3.74 1.05 2.2

⫻ 10⫺7 ⫻ 10⫺4 ⫻ 10⫺4 ⫻ 10⫺2 ⫻ 10⫺11

K 2 [SiF6 ] K 2 [ZrF6 ] KIO4 KClO4 K 2 Na[Co(NO2 )6] · H 2O

6.06 3.3 3.43 1.98 10.66

K[B(C 6 H 5 )4 ] K[UO2 AsO4 ] K 4 [UO2(CO3 )3 ]

7.66 22.60 4.20

2.2 ⫻ 10⫺8 2.5 ⫻ 10⫺23 6.3 ⫻ 10⫺5

Pr(OH)3

23.45

3.39 ⫻ 10⫺24

Pm(OH)3

21

Ra(IO3 )2 RaSO4

8.94 10.44

Rh(OH)3

23

Rb3 [Co(NO2 )6 ] Rb2 [PtCl 6 ] Rb2 [PtF6 ] Rb2 [SiF6 ] RbClO4 RbIO4

14.83 7.20 6.12 6.30 2.52 3.26

Ru(OH)3

36

Sm(OH)3

22.08

8.3 ⫻ 10⫺23

ScF3 Sc(OH)3

23.24 30.65

5.81 ⫻ 10⫺24 2.22 ⫻ 10⫺31

AgOAc Ag3 AsO4 AgN 3 AgBrO3 AgBr Ag2CO3 AgCl AgClO2 Ag2CrO4 Ag3 [Co(NO2 )6 ] Ag2CN 2 AgOCN AgCN Ag2Cr2O7 AgN(CN)2 Ag4 [Fe(CN)6 ] AgOH Ag2 N 2O2 AgIO3

2.71 21.99 8.54 4.27 12.27 11.07 9.75 3.70 11.95 20.07 10.14 6.64 16.22 6.70 8.85 40.81 7.71 18.89 7.50

1.94 1.03 2.8 5.38 5.35 8.46 1.77 2.0 1.12 8.5 7.2 2.3 5.97 2.0 1.4 1.6 2.0 1.3 3.17

1 ⫻ 10⫺21 1.16 ⫻ 10⫺9 3.66 ⫻ 10⫺11 1 ⫻ 10⫺23 1.5 6.3 7.7 5.0 3.0 5.5

⫻ 10⫺15 ⫻ 10⫺8 ⫻ 10⫺7 ⫻ 10⫺7 ⫻ 10⫺3 ⫻ 10⫺4

1 ⫻ 10⫺36

⫻ 10⫺3 ⫻ 10⫺22 ⫻ 10⫺9 ⫻ 10⫺5 ⫻ 10⫺13 ⫻ 10⫺12 ⫻ 10⫺10 ⫻ 10⫺4 ⫻ 10⫺12 ⫻ 10⫺21 ⫻ 10⫺11 ⫻ 10⫺7 ⫻ 10⫺17 ⫻ 10⫺7 ⫻ 10⫺9 ⫻ 10⫺41 ⫻ 10⫺8 ⫻ 10⫺19 ⫻ 10⫺8

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INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.15

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TABLE 8.6 Solubility Product Constants (Continued) Compound iodide molybdate nitrite oxalate phosphate quinaldate perrhenate selenate selenite selenocyanate sulfate sulfite sulfide thiocyanate vanadate tungstate Sodium ammonium cobaltinitrite antimonate hexafluoroaluminate uranyl arsenate Strontium arsenate carbonate chromate fluoride iodate iodate hydrate molybdate niobate oxalate hydrate phosphate 8-quinolinolate selenate selenite sulfate sulfite tungstate Terbium hydroxide Tellurium hydroxide Thallium(I) azide bromate bromide chloride chromate ferrocyanide dihydrate hexachloroplatinate iodate iodide

Formula

top of rh base of rh

pKsp

Ksp

AgI Ag2MoO4 AgNO2 Ag2C 2O4 Ag3 PO4 AgL AgReO4 Ag2SeO4 Ag2SeO3 AgSeCN Ag2SO4 Ag2SO3 Ag2S AgSCN AgVO3 Ag2WO4

16.07 11.55 3.22 11.27 16.05 16.89 4.10 7.25 15.00 15.40 4.92 13.82 49.20 11.99 6.3 11.26

8.52 2.8 6.0 5.40 8.89 1.3 8.0 5.7 1.0 4.0 1.20 1.50 6.3 1.03 5 5.5

⫻ 10⫺17 ⫻ 10⫺12 ⫻ 10⫺4 ⫻ 10⫺12 ⫻ 10⫺17 ⫻ 10⫺17 ⫻ 10⫺5 ⫻ 10⫺8 ⫻ 10⫺15 ⫻ 10⫺16 ⫻ 10⫺5 ⫻ 10⫺14 ⫻ 10⫺50 ⫻ 10⫺12 ⫻ 10⫺7 ⫻ 10⫺12

Na(NH4 )2 [Co(NO2 )6 ] Na[Sb(OH)6 ] Na 2 [AlF6 ] NaUO2 AsO4

10.66 7.4 9.39 21.87

2.2 4 4.0 1.3

⫻ 10⫺11 ⫻ 10⫺8 ⫻ 10⫺10 ⫻ 10⫺22

Sr3 (AsO4 )2 SrCO3 SrCrO4 SrF2 Sr(IO3 )2 Sr(IO3 )2 · H 2O SrMoO4 Sr(NbO3 )2 SrC 2O4 · H 2O Sr3 (PO4 )2 SrL 2 SrSeO4 SrSeO3 SrSO4 SrSO3 SrWO4

18.37 9.25 4.65 8.36 6.94 6.42 6.7 17.38 6.80 27.39 9.3 3.09 5.74 6.46 7.4 9.77

4.29 5.60 2.2 4.33 1.14 3.77 2 4.2 1.6 4.0 5 8.1 1.8 3.44 4 1.7

⫻ 10⫺19 ⫻ 10⫺10 ⫻ 10⫺5 ⫻ 10⫺9 ⫻ 10⫺7 ⫻ 10⫺7 ⫻ 10⫺7 ⫻ 10⫺18 ⫻ 10⫺7 ⫻ 10⫺28 ⫻ 10⫺10 ⫻ 10⫺4 ⫻ 10⫺6 ⫻ 10⫺7 ⫻ 10⫺8 ⫻ 10⫺10

Tb(OH)3

21.70

2.0 ⫻ 10⫺22

Te(OH)4

53.52

3.0 ⫻ 10⫺54

TlN 3 TlBrO3 TlBr TlCl Tl 2CrO4 Tl 4 [Fe(CN)6 ] · 2H 2O Tl 2 [PtCl 6 ] TlIO3 TlI

3.66 4.96 5.43 3.73 12.06 9.3 11.40 5.51 7.26

2.2 1.10 3.71 1.86 8.67 5 4.0 3.12 5.54

⫻ 10⫺4 ⫻ 10⫺5 ⫻ 10⫺6 ⫻ 10⫺4 ⫻ 10⫺13 ⫻ 10⫺10 ⫻ 10⫺12 ⫻ 10⫺6 ⫻ 10⫺8

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8.16

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SECTION 8

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TABLE 8.6 Solubility Product Constants (Continued) Compound oxalate selenate selenite sulfide thiocyanate Thallium(III) hydroxide 8-quinolinolate Thorium hydrogen phosphate hydroxide iodate oxalate phosphate Thullium hydroxide Tin (II) hydroxide (IV) hydroxide (II) sulfide Titanium (III) hydroxide (IV) oxide hydroxide Uranium(IV) fluoride 2.5-water Uranyl(VI)(2⫹) carbonate ferrocyanide hydrogen arsenate hydrogen phosphate hydroxide iodate hydrate oxalate trihydrate phosphate sulfite thiocyanate Vanadium (IV) hydroxide (III) phosphate Ytterbium hydroxide Yttrium carbonate fluoride hydroxide iodate oxalate Zinc anthranilate arsenate borate hydrate carbonate ferrocyanide

Formula

pKsp

Ksp ⫻ 10⫺4 ⫻ 10⫺4 ⫻ 10⫺39 ⫻ 10⫺21 ⫻ 10⫺4

Tl 2C 2O4 Tl 2SeO4 Tl 2SeO3 Tl 2S TlSCN

3.7 4.00 38.7 20.30 3.80

2 1.0 2 5.0 1.57

Tl(OH)3 TlL 3

43.77 32.40

1.68 ⫻ 10⫺44 4.0 ⫻ 10⫺33

Th(HPO4 )2 Th(OH)4 Th(IO3 )4 Th(C 2O4 )2 Th 3 (PO4 )4

20 44.40 14.60 22 78.60

1 4.0 2.5 1 2.5

Tm(OH)3

23.48

3.3 ⫻ 10⫺24

Sn(OH)2 Sn(OH)4 SnS

27.26 56 25.00

5.45 ⫻ 10⫺28 1 ⫻ 10⫺56 1.0 ⫻ 10⫺25

Ti(OH)3 TiO(OH)2

40 29

UF4 · 2.5H 2O

21.24

5.7 ⫻ 10⫺22

UO2CO3 UO2 [Fe(CN)6 ] UO2 HAsO4 UO2 HPO4 UO2 (OH)2 UO2 (IO3 )2 · H 2O UO2C 2O4 · 3H 2O (UO2 )3 (PO4 )2 UO2SO3 (UO2 )(SCN)2

11.73 13.15 10.50 10.67 21.95 7.50 3.7 46.7 8.58 3.4

1.8 7.1 3.2 2.1 1.1 3.2 2 2 2.6 4

VO(OH)2 (VO2 )3 PO4

22.13 24.1

5.9 ⫻ 10⫺23 8 ⫻ 10⫺25

Yt(OH)3

23.60

2.5 ⫻ 10⫺24

Y2 (CO3 )3 YF3 Y(OH)3 Y(IO3 )3 Y2 (C2O4 )3

2.99 20.06 22.00 9.95 28.28

1.03 8.62 1.00 1.12 5.3

⫻ 10⫺3 ⫻ 10⫺21 ⫻ 10⫺22 ⫻ 10⫺10 ⫻ 10⫺29

ZnL 2 Zn 3 (AsO4 )2 Zn(BO2 )2 · H 2O ZnCO3 Zn 2 [Fe(CN)6 ]

9.23 27.55 10.18 9.94 15.40

5.9 2.8 6.6 1.46 4.0

⫻ 10⫺10 ⫻ 10⫺28 ⫻ 10⫺11 ⫻ 10⫺10 ⫻ 10⫺15

⫻ 10⫺20 ⫻ 10⫺45 ⫻ 10⫺15 ⫻ 10⫺22 ⫻ 10⫺79

1 ⫻ 10⫺40 1 ⫻ 10⫺29

⫻ 10⫺12 ⫻ 10⫺14 ⫻ 10⫺11 ⫻ 10⫺11 ⫻ 10⫺22 ⫻ 10⫺8 ⫻ 10⫺4 ⫻ 10⫺47 ⫻ 10⫺9 ⫻ 10⫺4

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RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.17

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TABLE 8.6 Solubility Product Constants (Continued) Compound

Formula

pKsp

fluoride hydroxide iodate dihydrate oxalate dihydrate phosphate quinaldate 8-quinolinolate selenide selenite hydrate sulfide

ZnF2 Zn(OH)2 Zn(IO3 )2 · 2H 2O ZnC 2O4 · 2H 2O Zn 3 (PO4 )2 ZnL 2 ZnL 2 ZnSe ZnSeO3 · H 2O ␣-ZnS ␤-ZnS

1.52 16.5 5.37 8.86 32.04 13.80 24.30 25.44 6.80 23.80 21.60

Zirconium oxide hydroxide phosphate

8.2.1

top of rh base of rh

ZrO(OH)2 Zr3 (PO4 )4

48.20 132

Ksp 3.04 3 4.1 1.38 9.0 1.6 5.0 3.6 1.57 1.6 2.5

⫻ 10⫺2 ⫻ 10⫺17 ⫻ 10⫺6 ⫻ 10⫺9 ⫻ 10⫺33 ⫻ 10⫺14 ⫻ 10⫺25 ⫻ 10⫺26 ⫻ 10⫺7 ⫻ 10⫺24 ⫻ 10⫺22

6.3 ⫻ 10⫺49 1 ⫻ 10⫺132

Proton-Transfer Reactions

The pKa values listed in Tables 8.7 and 8.8 are the negative (decadic) logarithms of the acidic dissociation constant, i.e., ⫺log10 Ka ⫽ pKa . For the general proton-transfer reaction HB ⫽ H⫹ ⫹ B the acidic dissociation constant is formulated as follows: Ka ⫽

[H⫹ ][B] [HB]

The most common charge types for the acid HB and its conjugate base B are CH3COOH ⫽ H⫹ ⫹ CH3COO⫺ (acetic acid, acetate ion) HSO⫺4 ⫽ H⫹ ⫹ SO24⫺ (hydrogen sulfate ion, sulfate ion) NH⫹4 ⫽ H⫹ ⫹ NH3 (ammonium ion, ammonia) Acids which have more than one acidic hydrogen ionize in steps, as shown for phosphoric acid: H3PO4 ⫽ H⫹ ⫹ H2PO4⫺

pK1 ⫽ 2.148

K1 ⫽ 7.11 ⫻ 10⫺3

H2PO4⫺ ⫽ H⫹ ⫹ HPO42⫺

pK2 ⫽ 7.198

K2 ⫽ 6.34 ⫻ 10⫺8

HPO42⫺ ⫽ H⫹ ⫹ PO34⫺

pK3 ⫽ 11.90

K3 ⫽ 1.26 ⫻ 10⫺12

If the basic dissociation constant Kb for the equilibrium such as NH3 ⫹ H2O ⫽ NH4⫹ ⫹ OH⫺ is required, pKb may be calculated from the relationship pKb ⫽ pKw ⫺ pKa

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DEAN #37261

TABLE 8.7 Proton Transfer Reactions of Inorganic Materials in Water at 25⬚C Substance

H 3 AuO3 Hf 4⫹ hydrolysis ␮ ⫽ 1 N 3 P3(NH 2 )6 Ho3⫹ hydrolysis ␮ ⫽ 0.3

9

10.329 10.93 0.82

INTERACTIVE

Gold(III) hydroxide Hafnium(IV) ion Hexaminotriphosphazene Holmium(III) ion

11.2 4.98(4) 5.92 9.246(2) 9.757 2.55 1.42 0.64 5.66 6.5 1.58 4 7.92 9.2(1) 12.67(3) 5.62 6.352(1) 6.77 ca. 9.3 ⫺1.15 3.95 8.9 1.75 7.34 6.00(5) 14.956(1) 8.10 9.0 8.03 3.8 8.27 2.92 pK3 4.75 ⬍11.7 ⫺0.12 ⬍3.2 8.04

pK2

LEFT

Cerium(III) ion Cerium(IV) ion Chromium(III) ion Cobalt(II) ion Cobalt(III) ion Copper(II) ion Curium(III) ion Deuterium oxide Dysprosium(III) ion Erbium(III) ion Europium(III) ion Fermium(III) ion Gadolinium(III) ion Gallium(III) ion

H 3 AlO3 Al3⫹ (aquo) Am3⫹ (aquo) ␮ ⫽ 0.1 NH ⫹4 ND3 H ⫹ HSb(OH)6 ⫽ Sb(OH)6⫺ ⫹ H ⫹ ␮ ⫽ 0.5 SbO⫹ ⫹ H 2O ⫽ Sb(OH)3 ⫹ H ⫹ ␮ ⫽ 1.0 pKb of Ba(OH)⫹ ␮ ⫽ 0.1 pK for hydrolysis of Bk3⫹ ␮ ⫽ 0.1 Be 2⫹ (aquo) ⫽ BeOH⫹ ⫹ H ⫹ ␮ ⫽ 1.0 Bi3⫹ ⫽ BiOH2⫹ ⫹ H ⫹ ␮ ⫽ 3.0 H 2 B4O7 Br2 ⫹ H 2O ⫽ HBrO ⫹ H ⫹ ⫹ Br⫺ Cd2⫹ (aquo) hydrolysis Ca2⫹ (aquo) hydrolysis Cf 3⫹ (aquo) hydrolysis ␮ ⫽ 0.1 CO2 (aquo) CO2 in D2O Ce 3⫹ (aquo) hydrolysis Hydrolysis to Ce(OH)3⫹ and Ce(OH)22⫹ Cr 3⫹ (aquo) hydrolysis Co2⫹ (aquo) hydrolysis Co3⫹ (aquo) hydrolysis m ⫽ 1 Cu2⫹ (aquo) hydrolysis Cm3⫹ (aquo) hydrolysis m ⫽ 0.1 D2O (molal scale) Dy 3⫹ (aquo) hydrolysis Er 3⫹ (aquo) hydrolysis ␮ ⫽ 3 Eu3⫹ (aquo) hydrolysis Fm3⫹ hydrolysis ␮ ⫽ 0.1 Gd3⫹ hydrolysis Ga3⫹ (successive values for hydrolysis)

pK1

(McGHP)

Aluminic acid Aluminum ion (aquo) Americium(III) ion Ammonium ion Ammonium-d3 Antimonic acid Antimony(III) ion Barium ion Berkelium(III) ion Beryllium(II) ion Bismuth(III) ion Boric acid, tetraBromine Cadmium ion Calcium ion Californium(III) ion Carbon dioxide

Formula or remarks

3.77 13.36 0.23 7.68(3)

8.18

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TABLE 8.7 Proton Transfer Reactions of Inorganic Materials in Water at 25⬚C (Continued) Substance

Formula or remarks

Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen

H 2S2O7 (theoretical prediction) H 2S2O6 H 2S2O4 H 2 F2 H 2GeO4 H 2SiF6 H 2S2O4 HBrO HClO HIO H 2 N 2O2 HIO3

disulfate dithionate dithionite fluoride germanate hexafluorosilicate hydrosulfite hypobromite hypochlorite hypoiodite hyponitrite iodate

0.35 8.55 7.537 10.5(5) 7.21 0.804

8.102 6.760

6.488

4.889 4.3 ⬃2 pK4 6.61 2.10 pK4 9.35 ⫺8 ⫺0.2 2.45 12.30 1.92 2.50

INTERACTIVE

H 4 P 2O 7

7.94(3)

RIGHT

Hydrogen diphosphate

0.27 pK3 8.50 2.739 2.223 2.596 9.28(10) 4.62 5.115 9.236 1.02 ⫺8.72(15) ⫺2.7 ⫺6.2(1) 3.58 1.94 0.74 3.46 9.21 8.97 1.279(⫹1) 2.0(⫹1) ⬃1 pK3 3.03 pK5 9.84 0.91 pK3 6.70 ⫺12 ⫺3.4 0.35 3.20(4) 9.01

(McGHP)

⫹ H 3 N 9 NH3⫹ HNSO(OH)2 H 2 NPO(OH)2 (26⬚C) H 3AsO4 D3 AsO4 HAsO2 HN 3 DN 3 (in D2O) H 3 BO3 HBrO3 (in formamide) HBr HClO3 (theoretical prediction) HCl DCl (in dimethylformamide) HClO2 H 2CrO4 HOCN HCN DCN (in D2O) ␮ ⫽ 0.11 (NH 2 )PO(OH) (30⬚C) (NH 2 )PO(SH) (20⬚C) (HO)2 PO(NH)PO(OH)(NH)PO(OH)2 ␮ ⫽ 0.1

pK2

DEAN #37261

Hydrazinium(2⫹) ion Hydrogen amidodisulfonate Hydrogen amidophosphate Hydrogen arsenate Hydrogen-d3 arsenate Hydrogen arsenite Hydrogen azide Hydrogen-d azide Hydrogen borate (3⫺) Hydrogen bromate Hydrogen bromide Hydrogen chlorate Hydrogen chloride Hydrogen-d chloride Hydrogen chlorite Hydrogen chromate Hydrogen cyanate Hydrogen cyanide Hydrogen-d cyanide Hydrogen diamidophosphate Hydrogen diamidothiophosphate Hydrogen diimidotriphosphate

pK1

11.45(10)

Source: J. J. Christensen, L. D. Hansen, and R. M. Izatt, Handbook of Proton Ionization Heats and Related Thermodynamic Quantities, Wiley-Interscience, New York, 1976; D. D. Perrin, Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution, 2d ed., Pergamon Press, 1982.

8.19

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DEAN #37261

TABLE 8.7 Proton Transfer Reactions of Inorganic Materials in Water at 25⬚C (Continued) Substance

Formula or remarks DIO3 (in D2O) HI H 2 MnO4 (35⬚C) ␮ ⫽ 0.1 HNO3 HNO2 HClO4 HIO4 H 2O2 H 3PO5 ␮ ⫽ 0.2

Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen

H 2SO5 HReO4 HTcO4 H 2CS4 H 4 XeO6 H 3 PO4

peroxosulfate perrhenate pertechnetate perthiocarbonate perxenate phosphate(3⫺)

⫺1.37(7) 3.14(1) ⫺1.6 1.64 11.64(2) 1.1 pK3 12.8 1.0 ⫺1.25 0.3 3.54 pK3 10.5 2.148(20) pK3 12.32(6) 7.780 1.23 1.43 3.89 2.62 9.60(10) 0.99 6.97 1.89 7.65(5) 2.64 6.27 0.5 4.69 7.16 1.99 pK3 6.62

10.15

5.5 9.86 7.24 7.198(10)

6.68(14) 1.66 11.0 8.30(15) 11.8(1) 1.99(1) 12.90 7.205 11.00(5) 11– 12 8.43

INTERACTIVE

D2 PO4 (in D2O) H 2 PHO2 H 2 PHO3 H 2SeO4 H 2Se ␮ ⫽ 0.03 H 2SeO3 H 4SiO4 H 2 NSO3 H H 2SO4 H 2S SO2 ⫹ H 2O ⫽ HSO⫺3 ⫽ H⫹ H 6TeO6 H 2Te (18⬚C) H 2TeO3 (20⬚C) HBF4 H 2Ni(CN)4 H 3CrO8 (30⬚C) ␮ ⫽ 3 H 4 P4O13 ␮ ⫽ 0.034

1.15 ⫺8.56

LEFT

Hydrogen-d2 phosphate Hydrogen phosphinate Hydrogen phosphonate Hydrogen selenate Hydrogen selenide Hydrogen selenite Hydrogen silicate(4⫺) Hydrogen sulfamate Hydrogen sulfate Hydrogen sulfide Hydrogen sulfite Hydrogen tellurate Hydrogen telluride Hydrogen tellurite Hydrogen tetrafluoroborate Hydrogen tetracyanonickelate Hydrogen tetraperoxochromate Hydrogen tetrapolyphosphate

pK2

(McGHP)

Hydrogen-d iodate Hydrogen iodide Hydrogen manganate(VI) Hydrogen nitrate Hydrogen nitrite Hydrogen perchlorate Hydrogen periodate Hydrogen peroxide Hydrogen peroxophosphate

pK1

6.59 2.64 pK4 8.2

8.20

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TABLE 8.7 Proton Transfer Reactions of Inorganic Materials in Water at 25⬚C (Continued) Substance

Formula or remarks

Hydrogen thiosulfate Hydrogen tripolyphosphate

H 2S2O3 H 3P3O9

Hydrogen triselenocarbonate Hydrogen trithiocarbonate Hydrogen tungstate Hydrogen vanadate(⫺1) Hydrogen vanadate(3⫺) Hydroxylamine-N,N-disulfonic acid Hydroxylamine O-sulfonate Imidodiphosphoric acid

H 2CSe3 H 2CS3 (20⬚C) H 2WO4 HVO3 H 3VO4 HON(SO3 H)2 ␮ ⫽ 1.6 ⫹ H 3 NOSO3⫺ ␮ ⫽ 1 (HO)2 PO(NH)PO(OH)2 ␮ ⫽ 0.2

Indium(III) ion Iridium(III) ion Iron(II) ion Iron(III) ion Lanthanum(III) ion Lead(II) ion Lead(IV) ion Lithium(I) ion Lutetium(III) ion Magnesium(II) ion Manganese(II) ion Manganese(III) ion Mercury(I) ion Mercury(II) ion Neodymium(III) ion Neptunium(III) ion Neptunium(IV) ion Neptunium(V) ion Nickel(II) ion Osmium tetroxide Palladium(II) ion Pentacyanoaquoferrate(II) ion

In3⫹ hydrolysis Ir 3⫹ hydrolysis ␮ ⫽ 1 Fe 2⫹ hydrolysis ␮ ⫽ 1 Fe 3⫹ hydrolysis La3⫹ hydrolysis Pb2⫹ hydrolysis ␮ ⫽ 0.3 Pb4⫹ hydrolysis Li⫹ Lu3⫹ hydrolysis Mg 2⫹ hydrolysis Mn2⫹ hydrolysis Mn3⫹ hydrolysis Hg22⫹ hydrolysis ␮ ⫽ 0.5 Hg2⫹ hydrolysis ␮ ⫽ 0.5 Nd3⫹ hydrolysis ␮ ⫽ 3 Np3⫹ hydrolysis ␮ ⫽ 0.3 Np4⫹ hydrolysis ␮ ⫽ 2 NpO⫹2 hydrolysis Ni2⫹ hydrolysis OsO4 hydrolysis ␮ ⫽ 1 Pd2⫹ (stepwise pKb values) Fe(CN)5(H 2O)3⫺ ␮ ⫽ 0.1

5.427 1.74 1.7

7.70 8.18 3.70 7.78(4) 2.85 pK4 9.72 4.28 5.20

3.2

2.65

INTERACTIVE

HSCN ␮ ⫽ 3 H 3 PO3S

3.5

RIGHT

Hydrogen thiocyanate Hydrogen thiophosphate

1.5 pK3 6.6 ⫺1.8 1.788 pK3 10.08 0.6 ⬃1 pK3 2.00(10) pK4 5.83(7) pK5 8.51(6) 1.16 2.68 2.20 3.80 3.78 pK3 11.85 1.48 ⬃2 pK3 7.08 3.54 4.37 6.8 2.19 9.06 7.8 1.8 13.8 7.94 11.41 10.59 0.4 5.0 3.70 9.0(5) 7.43 2.30 8.90(2) 9.86 12.1 13.0 2.63

(McGHP)

H 3PS4

pK2

DEAN #37261

Hydrogen tetrathiophosphate

pK1

12.8

8.21

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short standard

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DEAN #37261

TABLE 8.7 Proton Transfer Reactions of Inorganic Materials in Water at 25⬚C (Continued) Substance

Formula or remarks

Pr 3⫹ hydrolysis ␮ ⫽ 0.3 Pa4⫹ hydrolysis ␮ ⫽ 3 Pa5⫹ hydrolysis ␮ ⫽ 3 Sc3⫹ hydrolysis ␮ ⫽ 0.05 Ag ⫹ hydrolysis Na⫹ (aquo) Sr 2⫹ (aquo) Tb3⫹ hydrolysis ␮ ⫽ 0.3 Tl⫹ Tl3⫹ hydrolysis ␮ ⫽ 3 Th4⫹ hydrolysis ␮ ⫽ 0.5 Sn2⫹ hydrolysis ␮ ⫽ 3 Ti3⫹ hydrolysis ␮ ⫽ 3 ⫹ TiO2⫹ ⫹ H 2O ⫽ TiO(OH)⫹ ⫹ H pKw for T2O ⫽ T ⫹ ⫹ OH ⫺ U 4⫹ hydrolysis UO22⫹ ␮ ⫽ 0.035 V2⫹ hydrolysis V3⫹ hydrolysis VO2⫹ hydrolysis VO⫹2 (20⬚C) ␮ ⫽ 0.1 XeO3 ⫹ H 2O ⫽ HXeO⫺4 ⫹ H ⫹ Yb3⫹ hydrolysis Y 3⫹ hydrolysis ␮ ⫽ 0.3 Zn2⫹ hydrolysis Zr 4⫹ hydrolysis ␮ ⫽ 1

4.05 2.74 0.38

4.20

3.5

INTERACTIVE

Praseodymium(III) ion Protoactinium(IV) ion Protoactinium(V) ion Scandium(III) ion Silver(I) ion Sodium ion Strontium ion Terbium(III) ion Thallium(I) ion Thallium(III) ion Thorium(IV) ion Tin(II) ion Titanium(III) Titanium(IV) Tritium oxide Uranium(IV) ion Uranyl(VI) ion Vanadium(II) ion Vanadium(III) ion Vanadyl(IV) ion Vanadyl(V) ion Xenon trioxide Ytterbium(III) ion Yttrium(III) ion Zinc ion Zirconium(IV) ion

7.2(2) 1.26 9.7 3.33 0.48 pK3 5.58 8.55 0.14 1.05 4.58(3) ⬎11.1 14.67(10) 13.18 8.16 13.36(15) 1.14 3.89 3.81(10) 2.55 1.3 15.21 0.68 5.82 6.85 2.92 6.86(10) 1.83 10.5 7.99(6) 8.34 8.96 ⫺0.32 pK3 0.35

LEFT

Pu3⫹ hydrolysis ␮ ⫽ 0.07 Pu4⫹ hydrolysis ␮ ⫽ 2 PuO⫹2 hydrolysis ␮ ⫽ 0.003 PuO22⫹ hydrolysis Po4⫹ hydrolysis

pK2

(McGHP)

Plutonium(III) ion Plutonium(IV) ion Plutonium(V) ion Plutonium(VI) ion Polonium(IV) ion

pK1

0.06

8.22

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.23

If a desired organic acid is not entered in Table 8.8, a useful estimate of its pKa value can sometimes be obtained by making a comparison with recognizably similar compounds for which pKa values are known: (1) alkyl chains, alicyclic rings, or saturated carbocyclic rings fused to aromatic or heterocyclic rings can be replaced by methyl or ethyl groups; (2) acid-strengthening inductive and mesomeric effects of a nitro group attached to an aromatic ring are very similar to those of a nitrogen atom located at the same position in a heteroaromatic ring (e.g., 3-hydroxypyridine and 3-nitrophenol). Hammett and Taft substituent constants and, in particular, Tables 9.1 through 9.4 may also prove useful for estimating pKa values.

8.2.1.1

top of rh base of rh cap height base of text

Calculation of the Approximate pH Value of Solutions

Strong acid:

pH ⫽ ⫺log [acid]

Strong base:

pH ⫽ 14.00 ⫹ log [base]

Weak acid:

pH ⫽ 1⁄2pKa ⫺ 1⁄2 log [acid]

Weak base:

pH ⫽ 14.00 ⫺ 1⁄2pKb ⫹ 1⁄2 log [base]

Salt formed by a weak acid and a strong base: pH ⫽ 7.00 ⫹ 1⁄2pKa ⫹ 1⁄2 log [salt] Acid salts of a dibasic acid: pH ⫽ 1⁄2pK1 ⫹ 1⁄2pK2 ⫺ 1⁄2 log [salt] ⫹ 1⁄2 log (K1 ⫹ [salt]) Buffer solution consisting of a mixture of a weak acid and its salt: pH ⫽ pKa ⫹ log

8.2.1.2

冉

冊

[salt] ⫹ [H3O⫹ ] ⫺ [OH⫺] [acid] ⫺ [H3O⫹] ⫹ [OH⫺]

Calculation of Concentrations of Species Present at a Given pH

␣0 ⫽ ␣1 ⫽ ␣2 ⫽

[H⫹]n [H A] ⫽ n [H⫹]n ⫹ K1[H⫹]n ⫺ 1 ⫹ K1 K2[H⫹]n ⫺ 2 ⫹ · · · ⫹ K1 K2 · · · Kn Cacid [H ] ⫹ K1[H ]

K1[H⫹]n ⫺ 1 [Hn ⫺ 1A⫺] ⫽ ⫹ n⫺2 ⫹ K1 K2[H ] ⫹ · · · ⫹ K1 K2 · · · Kn Cacid

[H ] ⫹ K1[H ]

K1K2[H⫹]n ⫺ 2 [H A2⫺] ⫽ n⫺2 ⫹ n⫺2 ⫹ K1 K2[H ] ⫹ · · · ⫹ K1 K2 · · · Kn Cacid

⫹ n

⫹ n

⫹ n⫺1

⫹ n⫺1

⯗

␣n ⫽

[H ] ⫹ K1[H ] ⫹ n

⫹ n⫺1

K1 K2 · · · Kn [An ⫺ ] ⫽ ⫹ n⫺2 ⫹ K1 K2[H ] ⫹ · · · ⫹ K1 K2 · · · Kn Cacid short standard long

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C Ionic strength ␮ is zero unless otherwise indicated. Protonated cations are designated by (⫹1), (⫹ 2), etc., after the pKa value; neutral species by (0), if not obvious; and negatively charged acids by (⫺1), (⫺2), etc. Substance Abietic acid Acetamide Acetamidine N-(2-Acetamido)-2-aminoethanesulfonic acid (20⬚C) 2-Acetamidobenzoic acid 3-Acetamidobenzoic acid 4-Acetamidobenzoic acid 2-(Acetamido)butanoic acid N-(2-Acetamido)iminodiacetic acid (20⬚C) 3-Acetamidopyridine Acetanilide Acetic acid Acetic acid-d (in D2O) Acetoacetic acid (18⬚C) Acetohydrazine Acetone oxime 2-Acetoxybenzoic acid (acetylsalicyclic acid) 3-Acetoxybenzoic acid 4-Acetoxybenzoic acid Acetylacetic acid (18⬚C) N-Acetyl-␣-alanine N-Acetyl-␤-alanine 2-Acetylaminobutanoic acid 3-Acetylaminopropionic acid 2-Acetylbenzoic acid 3-Acetylbenzoic acid 4-Acetylbenzoic acid 2-Acetylcyclohexanone N-Acetylcysteine (30⬚C) Acetylenedicarboxylic acid N-Acetylglycine N-Acetylguanidine N-␣-Acetyl-L-histidine Acetylhydroxamic acid (20⬚C) N-Acetyl-2-mercaptoethylamine 4-Acetyl-␤-mercaptoisoleucine (30⬚C) 2-Acetyl-1-naphthol (30⬚C) N-Acetylpenicillamine (30⬚C) 2-Acetylphenol 4-Acetylphenol 2-Acetylpyridine 3-Acetylpyridine 4-Acetylpyridine Aconitine Acridine Acrylic acid Adenine

pK1

pK2

pK3

pK4

7.62 ⫺0.37(⫹1) 1.60(⫹1) 6.88 3.63 4.07 4.28 3.716 6.62 4.37(⫹1) 0.4(⫹1) 4.756 5.32 3.58 3.24(⫹1) 12.2 3.48 4.00 4.38 3.58 3.715 4.455 3.72 4.445 4.13 3.83 3.70 14.1 9.52 1.75 3.670 8.23(⫹1) 7.08 9.40 9.92(SH) 10.30 13.40 9.90 9.19 8.05 2.643(⫹1) 3.256(⫹1) 3.505(⫹1) 8.11(⫹1) 5.60(⫹1) 4.26 4.17(⫹1)

13.39(0)40⬚C

4.40

9.75(0)

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

Adeninedeoxyriboside-5⬘-phosphoric acid Adenine-N-oxide Adenosine Adenosine-5⬘-diphosphoric acid Adenosine-2⬘-phosphoric acid Adenosine-3⬘-phosphoric acid Adenosine-5⬘-phosphoric acid Adenosine-5⬘-triphosphoric acid Adipamic acid (adipic acid monoamide) Adipic acid ␣-Alanine ␤-Alanine ␣-Alanine, methyl ester (␮ ⫽ 0.10) ␤-Alanine, methyl ester (␮ ⫽ 0.10) N-D-Alanyl-␣-D-alanine (␮ ⫽ 0.1) N-L-Alanyl-␣-L-alanine (␮ ⫽ 0.1) N-L-Alanyl-␣-D-alanine N-␣-Alanylglycine Alanylglycylglycine ␤-Alanylhistidine Albumin (bovine serum (␮ ⫽ 0.15) 2-Aldoxime pyridine Alizarin Black SN Alizarin-3-sulfonic acid Allantoin Allothreonine Alloxanic acid Allylacetic acid Allylamine 5-Allylbarbituric acid 5-Allyl-5-(-methylbutyl)barbituric acid 2-Allylphenol 1-Allylpiperidine 2-Allylpropionic acid 3-Amidotetrazoline 2-Aminoacetamide Aminoacetonitrile 9-Aminoacridine (20⬚C) 4-Aminoantipyrine 2-Aminobenzenesulfonic acid 3-Aminobenzenesulfonic acid 4-Aminobenzenesulfonic acid 2-Aminobenzoic acid 3-Aminobenzoic acid 4-Aminobenzoic acid 2-Aminobenzoic acid, methyl ester 3-Aminobenzoic acid, methyl ester 4-Aminobenzoic acid, methyl ester 3-Aminobenzonitrile 4-Aminobenzonitrile

—

pK2 4.4

2.69(⫹1) 3.5(⫹1) — 3.81(⫹1) 3.65(0) 3.74(0) — 4.629

8.49(0) 12.34(0) 4.2(⫺1) 6.17(0) 5.88(⫺1) 6.05(⫺1) 4.00(⫺1)

4.418 2.34(⫹1) 3.55(⫹1) 7.743(⫹1) 9.170(⫹1) 3.32(⫹1) 3.32(⫹1) 3.12(⫹1) 3.11(⫹1) 3.190(⫹1) 2.64 10– 10.3

5.412 9.69(0) 10.238(0)

3.42(⫹1) 5.79 5.54 8.96 2.108(⫹1) 6.64 4.68 9.69(⫹1) 4.78(⫹1) 8.08

10.22(0) 12.8 11.01

10.28 9.65(⫹1) 4.72 3.95(⫹1) 7.95(⫹1) 5.34(⫹1) 9.95(⫹1) 4.94(⫹1) 2.459(0) 3.738(0) 3.227(0) 2.09(⫹1) 3.07(⫹1) 2.41(⫹1) 2.36(⫹1) 3.58(⫹1) 2.45(⫹1) 2.75(⫹1) 1.74(⫹1)

8.13(0) 8.13(0) 8.30(0) 8.11(0) 8.15(0) 6.86

top of rh base of rh

pK3

pK4

6.4

7.20(⫺2)

13.06(⫺2) 6.48(⫺2)

9.40

9.096(0)

4.79(0) 4.79(0) 4.85(0)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

4-Aminobenzophenone 2-Aminobenzothiazole (20⬚C) 2-Aminobenzoylhydrazide 2-Aminobiphenyl 3-Aminobiphenyl 4-Aminobiphenyl 4-Amino-3-bromomethylpyridine 4-Amino-3-bromopyridine (20⬚C) 2-Aminobutanoic acid 3-Aminobutanoic acid 4-Aminobutanoic acid 2-Aminobutanoic acid, methyl ester (␮ ⫽ 0.1) 4-Aminobutanoic acid, methyl ester (␮ ⫽ 0.1) D-(⫹)-2-Amino-1-butanol 3-Amino-N-butyl-3-methyl-2butanone oxime 4-Aminobutylphosphonic acid 2-Amino-N-carbamoylbutanoic acid 4-Amino-N-carbamoylbutanoic acid 2-Amino-N-carbamoyl-2-methylpropanoic acid 1-Amino-1-cycloheptanecarboxylic acid 1-Amino-1-cyclohexanecarboxylic acid 2-Amino-1-cyclohexanecarboxylic acid 1-Aminocyclopentane 1-Aminocyclopropane 10-Aminodecylphosphonic acid 10-Aminodecylsulfonic acid 1-Amino-2-di(aminomethyl)butane 2-Amino-N,N-dihydroxyethyl-2hydroxyl-1,3-propanediol 2-Amino-N,N-dimethylbenzoic acid 4-Amino-2,5-dimethylphenol 4-Amino-3,5-dimethylpyridine (20⬚C) 12-Aminododecanoic acid 2-Aminoethane-1-phosphoric acid 1-Aminoethanesulfonic acid 2-Aminoethanesulfonic acid 2-Aminoethanethiol (cysteamine) (␮ ⫽ 0.01) 2-Aminoethanol (ethanolamine) 2-[2-(2-Aminoethyl)aminoethyl]pyridine 2-Amino-2-ethyl-1-butanol 3-(2-Aminoethyl)indole

2.15(⫹1) 4.48(⫹1) 1.85 3.78(⫹1) 4.18(⫹1) 4.27(⫹1) 7.47(⫹1) 7.04(⫹1) 2.286(⫹1) — 4.031(⫹1) 7.640(⫹1)

pK2

3.47

pK3

pK4

12.80

9.830(0) 10.14(0) 10.556(0)

9.838(⫹1) 9.52(⫹1) 9.09(⫹1) 2.55 3.886(⫹1)

7.55

10.9

4.683(⫹1) 4.463 2.59(⫹1)

10.46(0)

2.65(⫹1)

10.03(0)

3.56(⫹1)

10.21(0)

10.65(⫹1) 9.10(⫹1) — 2.65(⫹1) 3.58(⫹3) 6.484(⫹1) 1.63(⫹1) 5.28(⫹1) 9.54(⫹1) 4.648(⫹1) 5.838 ⫺0.33 1.5 8.23(⫹1) 9.50(⫹1) 3.50 9.82(⫹1) —

8.0 8.59(⫹2)

11.25 9.66(⫹1)

8.42(0) 10.40(0)

10.64 9.06 9.061

6.59

10.2

9.51

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8.27

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

3-Amino-N-ethyl-3-methyl-2-butanone oxime N-(2-Aminoethyl)morpholine p-(2-Aminoethyl)phenol 2-Aminoethylphosphonic acid N-(2-Aminoethyl)piperidine (30⬚C) 2-(2-Aminoethyl)pyridine (␮ ⫽ 0.5) 4-Amino-3-ethylpyridine (20⬚C) N-(2-Aminoethyl)pyrrolidine (30⬚C) 2-Aminofluorine 2-Amino-D-␤-glucose (␮ ⫽ 0.05) 2-Amino-N-glycylbutanoic acid 7-Aminoheptanoic acid 2-Aminohexanoic acid 6-Aminohexanoic acid C-Amino-C-hydrazinocarbonylmethane 2-Amino-3-hydroxybenzoic acid L-2-Amino-3-hydroxybutanoic acid (threonine) DL-2-Amino-4-hydroxybutanoic acid (␮ ⫽ 0.1) DL-4-Amino-3-hydroxybutanoic acid (␮ ⫽ 0.1) 2-Amino-2⬘-hydroxydiethyl sulfide 4-Amino-2-hydroxypyrimidine (cytosine) 3-Amino-N-isopropyl-3-methyl-2butanone oxime 4-Amino-3-isopropylpyridine (20⬚C) 1-Aminoisoquinoline (20⬚C, ␮ ⫽ 0.01) 3-Aminoisoquinoline (20⬚C, ␮ ⫽ 0.005) 4-Aminoisoxazolidine-3-one Aminomalonic acid DL-2-Amino-4-mercaptobutanoic acid 2-Amino-3-mercapto3-Methylbutanoic acid 2-Amino-6-methoxybenzothiazole 3-Amino-4-methylbenzenesulfonic acid 4-Amino-3-methylbenzenesulfonic acid 2-Amino-4-methylbenzothiazole 1-Amino-3-methylbutane 3-Amino-3-methyl-2-butanone oxime 3-Amino-N-methyl-3-methyl-2-butanone oxime

9.23(⫹1) 4.06(⫹2) 9.3 2.45(⫹1) 6.38 4.24(⫹2) 9.51(⫹1) 6.56(⫹2)

pK2

9.15(⫹1) 10.9 7.0(0) 9.89 9.78(⫹1)

pK3

pK4

10.8(⫺1)

9.74(⫹1)

10.34(⫹1) 2.20(⫹1) 3.155(⫹1) 4.502 2.335(⫹1) 4.373(⫹1) 2.38(⫹2)

9.834(0) 10.804(0) 7.69(⫹1)

2.5(⫹1) 2.088(⫹1)

5.192(0) 9.100(0)

2.265(⫹1)

9.257(0)

3.834(⫹1)

9.487(0)

9.27(⫹1) 4.58(⫹1)

top of rh base of rh

9.08(0) 8.331(0)

10.118(OH)

12.15(0)

9.09(⫹1) 9.54(⫹1) 7.62(⫹1) 5.05(⫹1) 7.4(⫹1) 3.32(⫹1) 2.22(⫹1)

9.83(0) 8.87(0)

10.86(SH)

1.8(⫹1)

7.9(0)

10.5(SH)

4.50(⫹1) 3.633 3.125 4.7(⫹1) 10.64(⫹1) 9.09(⫹1) 9.23(⫹1)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

pK2

2-Amino-3-methylpentanoic acid 3-Aminomethyl-6-methylpyridine (30⬚C) Aminomethylphosphonic acid 2-Amino-2-methyl-1,3-propanediol 2-Amino-2-methyl-1-propanol 2-Amino-2-methylpropanoic acid (2-Aminomethyl(pyridine (␮ ⫽ 0.5) 2-Amino-3-methylpyridine 4-Amino-3-methylpyridine 2-Amino-4-methylpyridine 2-Amino-5-methylpyridine 2-Amino-6-methylpyridine 2-Amino-4-methylpyrimidine (20⬚C) Aminomethylsulfonic acid N-Aminomorpholine 4-Amino-1-naphthalenesulfonic acid 1-Amino-2-naphthalenesulfonic acid 1-Amino-3-naphthalenesulfonic acid 1-Amino-5-naphthalenesulfonic acid 1-Amino-6-naphthalenesulfonic acid 1-Amino-7-naphthalenesulfonic acid 1-Amino-8-naphthalenesulfonic acid 2-Amino-1-naphthalenesulfonic acid 2-Amino-4-naphthalenesulfonic acid 2-Amino-6-naphthalenesulfonic acid 2-Amino-8-naphthalenesulfonic acid 3-Amino-1-naphthoic acid 4-Amino-2-naphthoic acid 8-Amino-2-naphthol DL-2-Aminopentanoic acid (DLnorvaline) 3-Aminopentanoic acid 4-Aminopentanoic acid 5-Aminopentanoic acid 5-Aminopentanoic acid, ethyl ester 2-Aminophenol 3-Aminophenol 4-Aminophenol 4-Aminophenylacetic acid (20⬚C) 2-Aminophenylarsonic acid

2.320(⫹1) 8.70(⫹1)

9.758(0)

2.35 8.801 9.694(⫹1) 2.357(⫹1) 2.31(⫹2)

5.9

pK3

pK4

10.8

10.205(0) 8.79(⫹1)

7.24(⫹1) 9.43(⫹1) 7.48(⫹1) 7.22(⫹1) 7.41(⫹1) 4.11(⫹1) 5.57(⫹1) 4.19(⫹1) 2.81 1.71 3.20 3.69 3.80 3.66 5.03 2.35 3.79 3.79

8.94

3.89 2.61 2.89 4.20(⫹1) 2.318(⫹1) 4.02(⫹1) 3.97(⫹1) 4.20(⫹1) 10.151 9.28 9.83 8.50 3.60 ca 2

4.39 4.46 9.808 10.399(0) 10.46(0) 9.758(0) 9.72 9.87 10.30 5.26 3.77

8.66

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8.29

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 3-Aminophenylarsonic acid 4-Aminophenylarsonic acid 3-Aminophenylboric acid 4-Aminophenylboric acid 4-Aminophenyl (4-chlorophenyl) sulfone 2-Aminophenylphosphonic acid 3-Aminophenylphosphonic acid 4-Aminophenylphosphonic acid 1-Amino-1,2,3-propanetricarboxylic acid (␮ ⫽ 2.2) 3-Aminopropanoic acid 1-Amino-1-propanol DL-2-Amino-1-propanol 3-Amino-1-propanol 3-Aminopropene 3-Amino-N-propyl-3-methyl-2-butanone oxime 2-Aminopropylsulfonic acid 2-Aminopyridine 3-Aminopyridine 4-Aminopyridine 2-Aminopyridine-1-oxide 3-Aminopyridine-1-oxide 4-Aminopyridine-1-oxide 8-Aminoquinaldine 2-Aminoquinoline (20⬚C, ␮ ⫽ 0.01) 3-Aminoquinoline (20⬚C, ␮ ⫽ 0.01) 4-Aminoquinoline (20⬚C, ␮ ⫽ 0.01) 5-Aminoquinoline (20⬚C, ␮ ⫽ 0.01) 6-Aminoquinoline (20⬚C, ␮ ⫽ 0.01) 8-Aminoquinoline (20⬚C, ␮ ⫽ 0.01) 4-Aminosalicyclic acid 5-Aminosalicyclic acid 2-Amino-3-sulfopropanoic acid 4-Amino-2,3,5,6-tetramethylpyridine (20⬚C) 5-Amino-1,2,3,4-tetrazole (20⬚C) 2-Aminothiazole (20⬚C) 1-Amino-3-thiobutane (30⬚C) 5-Amino-3-thio-1-pentanol (30⬚C) 2-Aminothiophenol 2-Amino-4,4,4-trifluorobutanoic acid 3-Amino-4,4,4-trifluorobutanoic acid 3-Amino-2,4,6-trinitroluene Angiotensin II

pK1

pK2

pK3

ca 2 ca 2 4.46 3.71 1.38

4.02 4.02 8.81 9.17

8.92 8.62

— — — 2.10(⫹1)

4.10 — — 3.60(0)

7.29 7.16 7.53 4.60(⫺1)

3.551(⫹1) 9.96(⫹1) 9.469(⫹1) 9.96(⫹1) 9.691(⫹1) 9.09(⫹1)

10.235(0)

— 6.71(⫹1) 6.03(⫹1) 9.114(⫹1) 2.58(⫹1) 1.47(⫹1) 3.54(⫹1) 4.86(⫹1) 7.34(⫹1)

top of rh base of rh

pK4

9.82(⫺2)

9.15

4.95(⫹1) 9.17(⫹1) 5.46(⫹1) 5.63(⫹1) 3.99(⫹1) 1.991(⫹1) 2.74(⫹1) 1.89(⫹1) 10.58(⫹1) 1.76 5.36(⫹1) 9.18(⫹1) 9.12(⫹1) ⬍2(⫹1)

3.917(0) 5.84(0) 8.70(0)

13.74

6.07

7.90(0) 8.171(0) 5.831(0) 9.5(⫹1)

10.37

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

Anhydroplatynecine Aniline 2-Anilinoethylsulfonic acid 3-Anilinoethylsulfonic acid Anthracene-1-carboxylic acid Anthracene-2-carboxylic acid Anthracene-9-carboxylic acid Anthraquinone-1-carboxylic acid (20⬚C) Anthraquinone-2-carboxylic acid (20⬚C) 9,10-Anthraquinone monoxime 9,10-Anthraquinone-1-sulfonic acid 9,10-Anthraquinone-2-sulfonic acid Antipyrine Apomorphine (15⬚C) D-(⫺)-Arabinose L-(⫹)-Arginine Arsenazo III [pK 5 10.5(⫺4); pK 6 12.0(⫺5)] Arsenoacetic acid Arsenoacrylic acid Arsenobutanoic acid 2-Arsenocrotonic acid 3-Arsenocrotonic acid Arsenopentanoic acid L-(⫹)-Ascorbic acid (vitamin C) L-(⫹)-Asparagine L-Asparaginylglycine D-Aspartic acid Aspartic diamide (␮ ⫽ 0.2) Aspartylaspartic acid ␣-Aspartylhistidine (38⬚C, ␮ ⫽ 0.1) ␤-Aspartylhistidine (38⬚C, ␮ ⫽ 0.1) N-Aspartyl-p-tyrosine (␮ ⫽ 0.01) Aspidospermine Atropine (17⬚C) 1-Azacycloheptane 1-Azacyclooctane Azetidine Aziridine

9.40 4.60(⫹1) 3.80(⫹1) 4.85(⫹1) 3.68 4.18 3.65 3.37

Barbituric acid m-Benzbetaine p-Benzbetaine Benzenearsonic acid (22⬚C) Benzene-1-arsonic acid-4-carboxylic acid Benzeneboronic acid Benzene-1-carboxylic acid-2-phosphoric acid Benzene-1-carboxylic acid-3-phosphoric acid

pK2

pK3

pK4

3.42 9.78 0.27 0.38 1.45(⫹1) 8.92 12.34 2.17

4.17 2.01(0) 1.89(0) 7.00

9.04(⫹1) 1.2 4.67 4.23 4.92 4.61 4.03 4.89 11.57 8.80(⫹1) 4.53 3.65 3.40 3.02 2.95 3.57

12.47(⫺1) 2.7

7.9(⫺3)

7.68 8.60 7.64 8.75 8.81 7.75

9.07 9.60 4.70 6.82 6.93 8.92

8.26 7.98 8.72 10.23(OH)

7.65 4.35(⫹1) 11.11(⫹1) 11.1(⫹1) 11.29(⫹1) 8.04(⫹1) 8.372(0) 3.217(⫹1) 3.245(⫹1) 8.48(⫺1) 4.22 (COOH)

5.59

3.78

9.17

4.03

7.03

13.7

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance Benzene-1-carboxylic acid-4-phosphoric acid Benzenediazine 1,3-Benzenedicarboxylic acid (isophthalic acid) 1,4-Benzenedicarboxylic acid (terephthalic acid) 1,3-Benzenedicarboxylic acid mononitrile 1,4-Benzenedicarboxylic acid mononitrile Benzenehexacarboxylic acid (pK 5 6.32; pK 6 7.49) Benzenepentacarboxylic acid (pK 5 6.46) Benzenesulfinic acid Benzenesulfonic acid 1,2,3,4-Benzenetetracarboxylic acid 1,2,3,5-Benzenetetracarboxylic acid 1,2,4,5-Benzenetetracarboxylic acid 1,2,3-Benzenetricarboxylic acid 1,2,4-Benzenetricarboxylic acid 1,3,5-Benzenetricarboxylic acid Benzil-␣-dioxime Benzilic acid Benzimidazole Benzohydroxamic acid (20⬚C) Benzoic acid 5,6-Benzoquinoline (20⬚C) 7,8-Benzoquinoline (20⬚C) 1,4-Benzoquinone monoxime Benzosulfonic acid 1,2,3-Benzotriazole 1-Benzoylacetone Benzoylamine 2-Benzoylbenzoic acid Benzoylglutamic acid N-Benzoyglycine (hippuric acid) Benzoylhydrazine Benzoylpyruvic acid 3-Benzoyl-1,1,1-trifluoroacetone Benzylamine Benzylamine-4-carboxylic acid 2-Benzyl-2-phenylsuccinic acid (20⬚C) 2-Benzylpyridine 4-Benzylpyridine-1-oxide 1-Benzylpyrrolidine 2-Benzylpyrrolidine Benzylsuccinic acid (20⬚C) 3-(Benzylthio)propanoic acid Berberine (18⬚C) Betaine

pK1 1.50

pK2 3.95

11.08(⫹1) 3.62(0)

4.60(⫺1)

3.54(0)

4.46(⫺1)

top of rh base of rh

pK3

pK4

6.89

3.60(0) 3.55(0) 0.68

2.21

3.52

5.09

1.80

2.73

3.96

5.25

3.25 3.51 2.87 4.75 3.84 4.10

4.73 4.44 4.49 7.13 5.20 5.18

6.21 5.81 5.63

1.50 2.554 2.05 2.38 1.92 2.88 2.52 2.12 12.0 3.09 5.53(⫹1) 8.89(0) 4.204 5.00(⫹1) 4.15(⫹1) 6.20 0.70 8.38(⫹1) 8.23 9.34(⫹1) 3.54 3.49 3.65 3.03(⫹2) 6.40 6.35 9.35(⫹1) 3.59 3.69 5.13(⫹1) ⫺1.018(⫹1) 9.51(⫹1) 10.31(⫹1) 4.11 4.463 11.73(⫹1) 1.832(⫹1)

12.3(0)

4.99 12.45(⫹1) 12.10

9.64 6.47

5.65

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

Biguanide 2,2⬘-Biimidazolyl (␮ ⫽ 0.3) 2-Biphenylcarboxylic acid (1,1⬘-Biphenyl)-4,4⬘-diamine Bis(2-aminoethyl) ether (30⬚C) N,N⬘-Bis(2-aminoethyl)-ethylenediamine (20⬚C) N,N-Bis(2-hydroxyethyl)-2-aminoethane sulfonic acid (BES) (20⬚C) N,N-Bis(2-hydroxyethyl)glycine (bicine) (20⬚C) Bis(2-hydroxyethyl)iminotris (hydroxymethyl)methane (bis-tris) 1,3-Bis[tris(hydroxymethyl)methylamino]propane (20⬚C) Bromoacetic acid 2-Bromoaniline 3-Bromoaniline 4-Bromoaniline 2-Bromobenzoic acid 3-Bromobenzoic acid 4-Bromobenzoic acid 2-Bromobutanoic acid (35⬚C) erythro-2-Bromo-3-chlorosuccinic acid (19⬚C, ␮ ⫽ 0.1) threo-2-Bromo-chlorosuccinic acid (19⬚C, ␮ ⫽ 0.1) trans-2-Bromocinnamic acid 3-Bromo-4-(dimethylamino)pyridine (20⬚C) 2-Bromo-4,6-dinitroaniline 3-Bromo-2-hydroxymethylbenzoic acid (20⬚C) 6-Bromo-2-hydroxymethylbenzoic acid (20⬚C) 7-Bromo-8-hydroxyquinoline-5sulfonic acid 3-Bromomandelic acid 3-Bromo-4-methylaminopyridine (20⬚C) (2-Bromomethyl)butanoic acid Bromomethylphosphonic acid 2-Bromo-6-nitrobenzoic acid 2-Bromophenol 3-Bromophenol 4-Bromophenol 2-(2⬘-Bromophenoxy)acetic acid 2-(3⬘-Bromophenoxy)acetic acid 2-(4⬘-Bromophenoxy)acetic acid 2-Bromo-2-phenylacetic acid 2-(Bromophenyl) acetic acid 4-(Bromophenyl)acetic acid

2.96(⫹2) 5.01(⫹1) 3.46 3.63(⫹2) 8.62(⫹2) 3.32(⫹4)

pK2

pK3

pK4

11.51(⫹1)

4.70(⫹1) 9.59(⫹1) 6.67(⫹3)

9.20(⫹2)

9.92(⫹1)

7.15

8.35 6.46(⫹1) 6.80(⫹1) 2.902 2.53(⫹1) 3.53(⫹1) 3.88(⫹1) 2.85 3.810 3.99 2.939 1.4

2.6

1.5

2.8

4.41 6.52(⫹1) ⫺6.94(⫹1) 3.28 2.25 2.51

6.70

3.13 7.49(⫹1) 3.92 1.14 1.37 8.452 9.031 9.34 3.12 3.09 3.13 2.21 4.054 4.188

6.52

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 4-Bromophenylarsonic acid 4-Bromophenylphosphinic acid (17⬚C) 2-Bromophenylphosphonic acid 3-Bromophenylphosphonic acid 4-Bromophenylphosphonic acid 3-Bromophenylselenic acid 4-Bromophenylselenic acid 2-Bromopropanoic acid 3-Bromopropanoic acid Bromopropynoic acid 2-Bromopyridine 3-Bromopyridine 4-Bromopyridine 3-Bromoquinoline Bromosuccinic acid 2-Bromo-p-tolylphosphonic acid Brucine (15⬚C) 2-Butanamine (sec-butylamine) 1,2-Butanediamine 1,4-Butanediamine 2,3-Butanediamine 1,2,3,4-Butanetetracarboxylic acid cis-2-Butenoic acid (isocrotonic acid) trans-2-Butenoic acid (trans-crotonic acid) (35⬚C) 3-Butenoic acid (vinylacetic acid) 3-Butoxybenzoic acid (20⬚C) Butylamine tert-Butylamine 4-tert-Butylaniline N-tert-Butylaniline Butylarsonic acid (18⬚C) 2-tert-Butylbenzoic acid 3-tert-Butylbenzoic acid 4-tert-Butylbenzoic acid N-Butylethylenediamine N-Butylglycine tert-Butylhydroperoxide 1-(tert-Butyl)-2-hydroxybenzene 1-(tert-Butyl)-3-hydroxybenzene 1-(tert-Butyl)-4-hydroxybenzene Butylmethylamine 2-Butyl-1-methyl-2-pyrroline 4-tert-Butylphenylactic acid Butylphosphinic acid tert-Butylphosphinic acid tert-Butylphosphonic acid 1-Butylpiperidine (␮ ⫽ 0.02) 2-tert-Butylpyridine 3-tert-Butylpyridine 4-tert-Butylpyridine

pK1 3.25 2.1 1.64 1.45 1.60 4.43 4.50 2.971 3.992 1.855 0.71(⫹1) 2.85(⫹1) 3.71(⫹1) 2.69(⫹1) 2.55 1.81 2.50(⫹2) 10.56(⫹1) 6.399(⫹2) 9.35(⫹2) 6.91(⫹2) 3.43 4.44

top of rh base of rh

pK2

pK3

pK4

8.19

7.00 6.69 6.83

4.41 7.15 8.16(⫹1) 9.388(⫹1) 10.82(⫹1) 10.00(⫹1) 4.58

5.85

7.16

4.676 4.68 4.25 10.64(⫹1) 10.685(⫹1) 3.78(⫹1) 7.10(⫹1) 4.23 3.57 4.199 4.389 7.53(⫹2) 2.35(⫹1) 12.80 10.62 10.119 10.23 10.90(⫹1) 11.84(⫹1) 4.417 3.41 4.24 2.79 10.43(⫹1) 5.76(⫹1) 5.82(⫹1) 5.99(⫹1)

8.91

10.30(⫹1) 10.25(0)

8.88

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 2-tert-Butylthiazole (␮ ⫽ 0.1) 4-tert-Butylthiazole (␮ ⫽ 0.1) 2-Butyn-1,4-dioic acid 2-Butynoic acid (tetrolic acid) Butyric acid 4-Butyrobetaine (20⬚C) Caffeine (40⬚C) Calcein (pK 5 ⬎12) Calmagite D-Camphoric acid Canaline Canavanine N-Carbamoylacetic acid N-Carbamoyl-␣-D-alanine N-Carbamoyl-␤-alanine DL-N-Carbamoylalanine N-Carbamoylglycine 2-Carbamoylpyridine (20⬚C) 3-Carbamoylpyridine 4-Carbamoylpyridine (20⬚C) ␤-Carboxymethylaminopropanoic acid Chloroacetic acid N-(2⬘-Chloroacetyl)glycine cis-3-Chloroacrylic acid (18⬚C, ␮ ⫽ 0.1) trans-3-chloroacrylic acid (18⬚C, ␮ ⫽ 0.1) 2-Chloroaniline 3-Chloroaniline 4-Chloroaniline 2-Chlorobenzoic acid 3-Chlorobenzoic acid 4-Chlorobenzoic acid 2-Chlorobutanoic acid 3-Chlorobutanoic acid 4-Chlorobutanoic acid 2-Chloro-3-butenoic acid 3-Chlorobutylarsonic acid (18⬚C) trans-2⬘-Chlorocinnamic acid trans-3⬘-Chlorocinnamic acid trans-4⬘-Chlorocinnamic acid 2-Chlorocrotonic acid 3-Chlorocrotonic acid Chlorodifluoroacetic acid 1-Chloro-1,2-dihydroxybenzene 1-Chloro-2,6-dimethyl-4-hydroxybenzene 4-Chloro-2,6-dinitrophenol 2-Chloroethylarsonic acid 3-Chlorohexyl-1-arsonic acid (18⬚C) 2-Chloro-3-hydroxybutanoic acid

pK1 3.00(⫹1) 3.04(⫹1) 1.75 2.620 4.817 3.94(⫹1) 10.4 ⬍4 8.14 4.57 2.40 2.50(⫹2) 3.64 3.89(⫹1) 4.99(⫹1) 3.892(⫹1) 3.876 2.10(⫹1) 3.328(⫹1) 3.61(⫹1) 3.61(⫹1)

pK2

pK3

pK4

4.40

5.4 12.35 5.10 3.70 6.60(⫹1)

9.0

10.5

9.20 9.25(0)

9.46(0)

2.867 3.38(0) 3.32 3.65 2.64(⫹1) 3.52(⫹1) 3.99(⫹1) 2.877 3.83 3.986 2.86 4.05 4.50 2.54 3.95 4.234 4.294 4.413 3.14 3.84 0.46 8.522 9.549 2.97 3.68 3.51 2.59

8.85

8.37 8.31

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8.35

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 3-Chloro-2-(hydroxymethyl)benzoic acid (20⬚C) 6-Chloro-2-(hydroxymethyl)benzoic acid (20⬚C) 7-Chloro-8-hydroxyquinoline-5sulfonic acid 2-Chloroisocrotonic acid 3-Chloroisocrotonic acid 3-Chlorolactic acid 3-Chloromandelic acid 3-Chloro-4-methoxyphenyl-phosphonic acid 3-Chloro-4-methylaniline 4-Chloro-N-methylaniline 4-Chloro-3-methylphenol Chloromethylphosphonic acid 2-Chloro-2-methylpropanoic acid 2-Chloro-6-nitroaniline 4-Chloro-2-nitroaniline 2-Chloro-3-nitrobenzoic acid 2-Chloro-4-nitrobenzoic acid 2-Chloro-5-nitrobenzoic acid 2-Chloro-6-nitrobenzoic acid 4-Chloro-2-nitrophenol 2-Chlorophenol 3-Chlorophenol 4-Chlorophenol (4-Chloro-3-nitrophenoxy)acetic acid 2-Chloro-4-nitrophenylphosphonic acid 3-Chloropentyl-1-arsonic acid (18⬚C) 2-Chlorophenoxyacetic acid 3-Chlorophenoxyacetic acid 4-Chlorophenoxyacetic acid 4-Chlorophenoxy-2-methylacetic acid 2-Chlorophenylacetic acid 3-Chlorophenylacetic acid 4-Chlorophenylacetic acid 2-Chlorophenylalanine 3-Chlorophenylalanine DL-4-Chlorophenylalanine 4-Chlorophenylarsonic acid 2-Chlorophenylphosphonic acid 3-Chlorophenylphosphonic acid 4-Chlorophenylphosphonic acid 3-(2⬘-Chlorophenyl)propanoic acid 3-(3⬘-Chlorophenyl)propanoic acid 3-(4⬘-Chlorophenyl)propanoic acid 3-Chlorophenylselenic acid 4-Chlorophenylselenic acid 4-Chloro-1,2-phthalic acid

pK1

pK2

top of rh base of rh

pK3

pK4

3.27 2.26 2.92

6.80

2.80 4.02 3.12 3.237 2.25

6.7

4.05(⫹1) 3.9(⫹1) 9.549 1.40 2.975 ⫺2.41(⫹1) ⫺1.10(⫹1) 2.02 1.96 2.17 1.342 6.48 8.55 9.10 9.43 2.959

6.30

1.12

6.14

3.71

8.77

3.05 3.07 3.10 3.26 4.066 4.140 4.190 2.23(⫹1) 2.17(⫹1) 2.08(⫹1) 3.33 1.63 1.55 1.66 4.577 4.585 4.607 4.47 4.48 1.60

8.94(0) 8.91(0) 8.96(0) 8.25 6.98 6.65 6.75

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

2-Chloropropanoic acid 3-Chloropropanoic acid 2-Chloropropylarsonic acid (18⬚C) 3-Chloropropylarsonic acid (18⬚C) Chloropropynoic acid 2-Chloropyridine 3-Chloropyridine 4-Chloropyridine 7-Chlorotetracycline 4-Chloro-2-(2⬘-thiazolylazo)phenol 4-Chlorothiophenol N-Chloro-p-toluenesulfonamide 3-Chloro-o-toluidine 4-Chloro-o-toluidine 5-Chloro-o-toluidine 6-Chloro-o-toludine Chrome Azurol S Chrome Dark Blue Cinchonine cis-Cinnamic acid trans-Cinnamic acid Citraconic acid Citric acid L-(⫹)-Citrulline Cocaine Codeine Colchicine Coniine (␮ ⫽ 0.5) Creatine (40⬚C) Creatinine o-Cresol m-Cresol p-Cresol Cumene hydroperoxide Cupreine Cyanamide Cyanoacetic acid Cyanoacetohydrazide 2-Cyanobenzoic acid 3-Cyanobenzoic acid 4-Cyanobenzoic acid 4-Cyanobutanoic acid trans-1-Cyanocyclohexane-2-carboxylic acid 4-Cyano-2,6-dimethylphenol 4-Cyano-3,5-dimethylphenol 2-Cyanoethylamine N-(2-Cyano)ethylnorcodeine Cyanomethylamine 2-Cyano-2-methyl-2-phenylacetic acid 1-Cyanomethylpiperidine 2-Cyano-2-methylpropanoic acid

2.84 3.992 3.76 3.63 1.854 0.49(⫹1) 2.84(⫹1) 3.83(⫹1) 3.30(⫹1) 7.09 5.9 4.54(⫹1) 2.49(⫹1) 3.385(⫹1) 3.85(⫹1) 3.62(⫹1) 2.45 7.56 5.85(⫹2) 3.879 4.438 2.29(0) 3.128 2.43(⫹1) 8.41(⫹1) 7.95(⫹1) 1.65(⫹1) 11.24(⫹1) 3.28(⫹1) 3.57(⫹1) 10.26 10.00 10.26 12.60 7.63(⫹1) 10.27 2.460 2.34(⫹2) 3.14 3.60 3.55 4.44 3.865

pK2

pK3

pK4

8.39 8.53

7.44

4.86 9.3 9.92(⫹1)

6.15(⫺1) 4.761 9.41(0)

9.27

11.47 12.4

6.396

11.17(⫹1)

8.27 8.21 7.7(⫹1) 5.68(⫹1) 5.34(⫹1) 2.290 4.55(⫹1) 2.422

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8.37

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 3-Cyanophenol o-Cyanophenoxyacetic acid m-Cyanophenoxyacetic acid p-Cyanophenoxyacetic acid 2-Cyanopropanoic acid 3-Cyanopropanoic acid 2-Cyanopyridine 3-Cyanopyridine 4-Cyanopyridine Cyanuric acid Cyclobutanecarboxylic acid 1,1-Cyclobutanedicarboxylic acid cis-1,2-Cyclobutanedicarboxylic acid trans-1,2-Cyclobutanedicarboxylic acid cis-1,3-Cyclobutanedicarboxylic acid trans-1,3-Cyclobutanedicarboxylic acid Cyclohexanecarboxylic acid 1,1-Cyclohexanediacetic acid cis-1,2-Cyclohexanediacetic acid (20⬚C) trans-1,2-Cyclohexanediacetic acid (20⬚C) cis-1,2-Cyclohexanediamine trans-1,2-Cyclohexanediamine 1,1-Cyclohexanedicarboxylic acid cis-1,2-Cyclohexanedicarboxylic acid (20⬚C) trans-1,2-Cyclohexanedicarboxylic acid (20⬚C) cis-1,3-Cyclohexanedicarboxylic acid (16⬚C) trans-1,3-Cyclohexanedicarboxylic acid (19⬚C) trans-1,4-Cyclohexanedicarboxylic acid (16⬚C) 1,3-Cyclohexanedione cis,cis-1,3,5-Cyclohexanetriamine Cyclohexanonimine cis-4-Cyclohexene-1,2-dicarboxylic acid (20⬚C) trans-4-Cyclohexene-1,2-dicarboxylic acid (20⬚C) Cyclohexylacetic acid Cyclohexylamine 2-(Cyclohexylamino)ethanesulfonic acid (CHES) (20⬚C) 3-Cyclohexylamino-1-propanesulfonic acid (CAPS) (20⬚C) 4-Cyclohexylbutanoic acid

pK1 8.61 2.98 3.03 2.93 2.37 3.99 ⫺0.26(⫹1) 1.45(⫹1) 1.90(⫹1) 6.78 4.785 3.13 3.90

pK2

top of rh base of rh

pK3

pK4

5.88 5.89

3.79

5.61

4.04

5.31

3.81

5.28

4.90 3.49 4.42

6.96 5.45

4.38

5.42

6.43(⫹2) 6.34(⫹2) 3.45 4.34

9.93(⫹1) 9.74(⫹1) 4.11 6.76

4.18

5.93

4.10

5.46

4.31

5.73

4.18

5.42

5.26 6.9(⫹3) 9.15 3.89

6.79

3.95

5.81

8.7(⫹2)

10.4(⫹1)

4.51 10.64(⫹1) 9.55 10.40 4.95

short standard long

DEAN #37261

LEFT

(McGHP)

8.38

INTERACTIVE

top of rh base of rh

SECTION 8

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance Cyclohexylcyanoacetic acid 1,2-Cyclohexylenedinitriloacetic acid (␮ ⫽ 0.1) 3-Cyclohexylpropanoic acid 2-Cyclohexylpyrrolidine 2-Cyclohexyl-2-pyrroline Cyclohexylthioacetic acid Cyclopentanecarboxylic acid cis-Cyclopentane-1-carboxylic acid-2-acetic acid trans-Cyclopentane-1-carboxylic acid-2-acetic acid Cyclopentane-1,2-diamine-N,N⬘,N⬘tetraacetic acid (␮ ⫽ 0.1) Cyclopentane-1,1-dicarboxylic acid cis-Cyclopentane-1,2-dicarboxylic acid trans-Cyclopentane-1,2-dicarboxylic acid cis-Cyclopentane-1,3-dicarboxylic acid trans-Cyclopentane-1,3-dicarboxylic acid Cyclopentylamine 1,1-Cyclopentyldiacetic acid cis-Cyclopentyl-1,2-diacetic acid trans-Cyclopentyl-1,2-diacetic acid Cyclopropanecarboxylic acid Cyclopropane-1,1-dicarboxylic acid cis-Cyclopropane-1,2-dicarboxylic acid trans-Cyclopropane-1,2-dicarboxylic acid Cyclopropylamine 5-Cyclopropyl-1,2,3,4-tetrazole L-Cysteic acid (3-sulfo-L-alanine) L-(⫹)-Cysteine L-(⫹)-Cysteine, ethyl ester

pK1 2.367 2.4 4.91 10.76(⫹1) 7.91(⫹1) 3.488 4.905 4.40 4.39 —

5.51

4.32

5.42

4.59 3.21 3.8(⫹1)

L-Cystine

—

4.26

Decanedioic acid (sebacic acid) Dehydroascorbic acid (20⬚C) 2⬘-Deoxyadenosine (␮ ⫽ 0.1)

L-Cysteinyl-L-asparagine

12.35

5.67

5.85

3.65

pK4

5.79

3.96

10.65(⫹1) 3.80 4.42 4.43 4.827 1.82 3.33

pK3

6.16

4.08 6.67

(35⬚C) Cystinylglycylglycine (35⬚C) Cytidine Cytidine-2⬘-phosphoric acid Cytidine-3⬘-phosphoric acid Cytidine-5⬘-phosphoric acid Cytosine

methyl ester

3.5

3.23 4.43

9.10(⫹1) 4.90(⫹1) 1.89(⫹1) 1.96 6.69 (NH 3⫹) 6.56 (NH 3⫹) 2.97 1.6(⫹2) 3.12 4.08(⫹1) 0.8(⫹1) 0.80(⫹1) — 4.58(⫹1)

L-(⫹)-Cysteine,

pK2

—

10.20

6.77 5.42 5.43 5.43 6.47 5.13

8.7(0) 8.18 9.17(SH)

10.29(SH)

8.99(SH) 7.09 2.1(⫹1) 3.21 12.24(0) 4.36(0) 4.31(0) 4.39(0) 12.15(0) 5.59 7.92

8.47 8.02(0) 6.01 6.17(⫺1) 6.04(⫺1) 6.62(⫺1)

10.3

8.71(⫺1) 6.87

13.2(sugar)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.39

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance Deoxycholic acid 2-Deoxyglucose 2-Deoxyguanosine (␮ ⫽ 0.1) 5-Desoxypyridoxal (␮ ⫽ 0) 1,1-Diacetic acid semicarbazide (30⬚C, ␮ ⫽ 0.1) Diacetylacetone Diallylamine (␮ ⫽ 0.02) 5,5-Diallybarbituric acid 1,3-Diamino-2-aminomethylpropane 3,5-Diaminobenzoic acid 1,3-Diamino-N,N⬘-bis-(2-aminoethyl)propane (␮ ⫽ 0.5) 2,4-Diaminobutanoic acid (20⬚C) 2,2⬘-Diaminodiethyl sulfide (30⬚C) 1,8-Diamino-3,6-dithiooctane (30⬚C) 2,7-Diaminooctanedioic acid (20⬚C, ␮ ⫽ 0.1) 1,8-Diamino-3,6-octanedione (30⬚C) 1,8-Diamino-3-oxa-6-thiooctane 2,3-Diaminopropanoic acid (␮ ⫽ 0.1) 2,3-Diaminopropanoic acid, methyl ester (␮ ⫽ 0.1) 1,3-Diamino-2-propanol (20⬚C) 2,5-Diaminopyridine (20⬚C) 1,4-Diazabicyclo[2.2.2]octane Dibenzylamine Dibenzylsuccinic acid (20⬚C) Dibromoacetic acid 3,5-Dibromoaniline 3,5-Dibromophenol 2,2-Dibromopropanoic acid 2,3-Dibromopropanoic acid rac-2,3-Dibromosuccinic acid (20⬚C) meso-2,3-Dibromosuccinic acid (20⬚C) 3,5-Dibromo-p-L-tyrosine Dibutylamine Di-sec-butylamine 2,6-Di-tert-butylpyridine rac-2,3-Di-tert-butylsuccinic acid (␮ ⫽ 0.1) 1,12-Dicarboxydodecaborane Dichloroacetic acid Dichloroacetylacetic acid 3,5-Dichloroaniline 1,3-Dichloro-2,5-dihydroxybenzene (␮ ⫽ 0.65)

pK1

pK2

pK3

6.58 12.52 2.5(⫹1) 4.17(⫹1) 2.96

8.14(OH) 4.04

7.42 9.29(⫹1) 7.78(0) 6.44(⫹3)

8.56(⫹2)

10.38(⫹1)

5.30 6.01(⫹4)

7.26(⫹3)

9.49(⫹2)

1.85(⫹2) 8.84(⫹2) 8.43(⫹2)

8.24(⫹1) 9.64(⫹1) 9.31(⫹1)

10.40(0)

1.84(⫹2)

2.64(⫹1)

9.23(0)

8.60(⫹2)

9.57(⫹1)

8.54(⫹2) 1.33(⫹2)

9.46(⫹1) 6.674(⫹1)

4.412(⫹1)

8.250(0)

7.93(⫹2) 2.13(⫹2) 2.90(⫹2) 8.52(⫹1) 3.96 1.39 2.35(⫹1) 8.056 1.48 2.33 1.43

9.69(⫹1) 6.48(⫹1) 8.60(⫹1)

1.51 2.17(⫹1) 11.25(⫹1) 10.91(⫹1) 3.58(⫹1) 3.58 9.07 1.26 2.11 2.37(⫹1) 7.30

top of rh base of rh

pK4

10.23(⫹1)

9.89(⫺1)

9.623(0)

6.66

2.24 2.71 6.45(0)

7.60(⫺1)

10.2 10.23

9.99

short standard long

DEAN #37261

LEFT

(McGHP)

8.40

INTERACTIVE

top of rh base of rh

SECTION 8

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 2,5-Dichloro-3,6-dihydroxy-p-benzoquinone Dichloromethylphosphonic acid 2,4-Dichloro-6-nitroaniline 2,5-Dichloro-4-nitroaniline 2,6-Dichloro-4-nitroaniline 2,3-Dichlorophenol 2,4-Dichlorophenol 2,6-Dichlorophenol 3,4-Dichlorophenol 3,5-Dichlorophenol 2,4-Dichlorophenoxyacetic acid (2,4-D) 4,6-Dichlorophenoxy-2-methylacetic acid 3,6-Dichlorophthalic acid 2,2-Dichloropropanoic acid 2,3-Dichloropropanoic acid rac-2,3-Dichlorosuccinic acid (20⬚C) meso-2,3-Dichlorosuccinic acid 3,5-Dichloro-p-tyrosine 2-Dicyanoethylamine 2,2-Dicyanopropanoic acid Dicyclohexylamine Dicyclopentylamine Didodecylamine Diethanolamine Di(ethoxyethyl)amine 3,5-Diethoxyphenol 3-(Diethoxyphosphinyl)benzoic acid 4-(Diethoxyphosphinyl)benzoic acid 3-(Diethoxyphosphinyl)phenol 4-(Diethoxyphosphinyl)phenol Diethylamine 2-(Diethylamino)ethyl-4-aminobenzoate ␣-(Diethylamino)toluene N,N-Diethylaniline 5,5-Diethylbarbituric acid (veronal) N,N-Diethylbenzylamine Diethylbiguanide (30⬚C) Diethylenetriamine Diethylenetriaminepentaacetic acid (pK 5 , 10.58) N,N-Diethylethylenediamine 2,2-Diethylglutaric acid N,N-Diethylglycine Diethylglycolic acid (18⬚C) Diethylmalonic acid Diethylmethylamine rac-2,3-Diethylsuccinic acid

pK1 1.09 1.14 ⫺3.00(⫹1) ⫺1.74(⫹1) ⫺3.31(⫹1) 7.44 7.85 6.78 8.630 8.179 2.64

pK2

pK3

pK4

2.42 5.61

3.13 1.46 2.06 2.85 1.43 1.49 2.12 5.14(⫹1) ⫺2.8 11.25(⫹1) 10.93(⫹1) 10.99(⫹1) 8.88(⫹1) 8.47(⫹1) 9.370 3.65

2.81 2.97 6.47

7.62

3.60 8.66 8.28 10.8(⫹1) 8.85(⫹1) 9.44(⫹1) 6.56(⫹1) 8.020(0) 9.48(⫹1) 2.53(⫹1) 4.42(⫹3) 1.80(0) 7.70(⫹2) 3.62 2.04(⫹1) 3.804 2.151 10.43(⫹1) 3.63

11.68(0) 9.21(⫹2) 2.55(⫺1)

10.02(⫹1) 4.33(⫺2)

8.60(⫺3)

10.46(⫹1) 7.12 10.47(0) 7.417 6.46

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.41

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance meso-2,3-Diethylsuccinic acid N,N-Diethyl-o-toluidine Difluoroacetic acid 3,3-Difluoroacrylic acid Diglycolic acid Diguanidine Dihexylamine Dihydroarecaidine Dihydroarecaidine, methyl ester Dihydrocodeine Dihydroergonovine ␣-Dihydrolysergic acid ␥-Dihydrolysergic acid ␣-Dihydrolysergol ␤-Dihydrolysergol Dihydromorphine 3,4-Dihydroxyalanine 1,2-Dihydroxyanthraquinone-3-sulfonic acid (alizarin-3-sulfonic acid) 3,4-Dihydroxybenzaldehyde 1,2-Dihydroxybenzene (pyrocatechol) (␮ ⫽ 0.1) 1,3-Dihydroxybenzene (resorcinol) 1,4-Dihydroxybenzene (hydroquinone) 4,5-Dihydroxybenzene-1,3-disulfonic acid 2,3-Dihydroxybenzoic acid (30⬚C) 2,4-Dihydroxybenzoic acid (␤-resorcyclic acid) 2,5-Dihydroxybenzoic acid 2,6-Dihydroxybenzoic acid 3,4-Dihydroxybenzoic acid 3,5-Dihydroxybenzoic acid 2,5-Dihydroxy-p-benzoquinone 3,4-Dihydroxy-3-cyclobutene-1,2dione 2,3-Dihydroxy-2-cyclopenten-1one (20⬚C) 1,4-Dihydroxy-2,6-dinitrobenzene Di(2,2⬘-hydroxyethyl)amine N,N-Di(2-hydroxyethyl)glycine Dihydroxymaleic acid Dihydroxymalic acid 1,3-Dihydroxy-2-methylbenzene (␮ ⫽ 0.65) 2,2-Di(hydroxymethyl)-3-hydroxypropanoic acid 2,4-Dihydroxy-5-methylpyrimidine 2,4-Dihydroxy-6-methylpyrimidine 1,4-Dihydroxynaphthalene (26⬚C, ␮ ⫽ 0.65) 1,2-Dihydroxy-3-nitrobenzene

pK1 3.54 7.18(⫹1) 1.33 3.17 2.96 12.8 11.0(⫹1) 9.70 8.39 8.75(⫹1) 7.38(⫹1) 3.57 3.60 8.30 8.23 9.35 2.32(⫹1) —

top of rh base of rh

pK2

pK3

pK4

6.59

8.45 8.71

8.68(0) 5.54(⫺1)

7.55 9.356(0)

12.98(⫺1)

9.44(0) 9.91(0)

12.32(⫺1) 12.04(⫺1)

—

—

2.98 3.29

10.14 8.98

2.97 1.30 4.48 4.04 2.71 0.541

10.50 8.67

9.87(⫺1) 11.01(⫺2)

7.66(⫺2)

12.6(⫺3)

11.74

5.18 3.480

4.72 4.42 8.8(⫹1) 8.333 1.10 1.92 10.05

9.14

11.64

4.460 9.90 9.52 9.37 6.68

10.93

short standard long

DEAN #37261

LEFT

(McGHP)

8.42

INTERACTIVE

top of rh base of rh

SECTION 8

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 1,2-Dihydroxy-4-nitrobenzene (␮ ⫽ 0.1) 2,4-Dihydroxy-1-phenylazobenzene (␮ ⫽ 0.1) 2,4-Dihydroxyoxazolidine 2,4-Dihydroxypteridine 2,6-Dihydroxypurine 2,4-Dihydroxypyridine (20⬚C) Dihydroxytartaric acid 1,4-Dihydroxy-2,3,5,6-tetramethylbenzene (␮ ⫽ 0.65) 3,5-Diiodoaniline 2,5-Diiodohistamine 2,5-Diiodohistidine (␮ ⫽ 0.1) 3,5-Diiodophenol 3,5-Diiodotyrosine Diisopropylmalonic acid Dilactic acid threo-1,4-Dimercapto-2,3-butanediol meso-2,3-Dimercaptosuccinic acid 3,5-Dimethoxyaniline 2,6-Dimethoxybenzoic acid 1,10-Dimethoxy-3,8-dimethyl-4,7phenanthroline Di(2-methoxyethyl)amine 3,5-Dimethoxyphenol (3,4-Dimethoxy)phenylacetic acid Dimethylamine 4-Dimethylaminobenzaldehyde N,N-Dimethylaminocyclohexane 4-Dimethylamino-2,3-dimethyl-1phenyl-3-pyrazolin-5-one 4-Dimethylamino-3,5-dimethylpyridine (20⬚C) 2-(Dimethylamino)ethanol 2-[2-(Dimethylamino)ethyl]pyridine 3-(Dimethylaminoethyl)pyridine 4-(Dimethylaminoethyl)pyridine 4-(Dimethylamino)-3-ethylpyridine (20⬚C) 4-(Dimethylamino)-3-isopropylpyridine (20⬚C) 2-(Dimethylaminomethyl)pyridine 3-(Dimethylaminomethyl)pyridine 4-(Dimethylaminomethyl)pyridine 4-(Dimethylamino)-3-methylpyridine (20⬚C) 4-(Dimethylaminophenyl)phosphonic acid 3-(Dimethylamino)propanoic acid 4-(Dimethylamino)pyridine (20⬚C)

pK1

pK2

pK3

pK4

6.701 11.98 6.11(⫹1) ⬍1.3 7.53(0) 1.37(⫹1) 1.95 11.25 2.37(⫹1) 2.31(⫹2) 2.72 8.103 2.117(⫹1) 2.124 2.955 8.9 2.71 3.86(⫹1) 3.44 7.21

7.92 11.84(⫺1) 6.45(0) 4.00 12.70

13(⫺1)

8.20(⫹1) 8.18

10.11(0) 9.76

6.479(0) 8.848

7.821(⫺1)

3.48

8.89(SH)

10.79(SH)

9.51(⫹1) 9.345 4.333 10.77(⫹1) 1.647(⫹1) 10.72(⫹1) 4.18(⫹1) 8.15(⫹1) 9.26(⫹1) 3.46(⫹2) 4.30(⫹2) 4.66(⫹2) 8.66(⫹1)

8.75(⫹1) 8.86(⫹1) 8.70(⫹1)

8.27(⫹1) 2.58(⫹2) 3.17(⫹2) 3.39(⫹2) 8.68(⫹1)

8.12(⫹1) 8.00(⫹1) 7.66(⫹1)

2.0(⫹1)

4.2

9.85(⫹1) 6.09(⫹1)

7.35

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.43

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

N,N-Dimethylaniline 2,3-Dimethylaniline 2,4-Dimethylaniline 2,5-Dimethylaniline 2,6-Dimethylaniline 3,4-Dimethylaniline 3,5-Dimethylaniline N,N-Dimethylaniline-4-phosphonic acid (17⬚C) Dimethylarsinic acid (cacodylic acid) 1,3-Dimethylbarbituric acid 2,3-Dimethylbenzoic acid 2,4-Dimethylbenzoic acid 2,5-Dimethylbenzoic acid 2,6-Dimethylbenzoic acid 3,4-Dimethylbenzoic 3,5-Dimethylbenzoic acid N,N-Dimethylbenzylamine Dimethylbiguanide 2,2-Dimethylbutanoic acid (18⬚C) Dimethylchlorotetracycline (␮ ⫽ 0.01) 2,6-Dimethyl-4-cyanophenol 3,5-Dimethyl-4-cyanophenol 5,5-Dimethyl-1,3-cyclohexanedione cis-3,3-Dimethyl-1,2-cyclopropanedicarboxylic acid trans-3,3-Dimethyl-1,2-cyclopropanedicarboxylic acid 3,5-Dimethyl-4-(dimethylamino)pyridine (20⬚C) 2,2-Dimethyl-1,3-dioxane-4,6dione 1,1-Dimethylethanethiol (␮ ⫽ 0.1) N,N-DimethylethylenediamineN,N-diacetic acid N,N⬘-DimethylethylenediamineN,N⬘-diacetic acid N,N-DimethylethylenediamineN,N⬘-diacetic acid N,N-Dimethylglycine Dimethylglycolic acid (18⬚C) N,N-Dimethylglycylglycine Dimethylglyoxime 5,5-Dimethyl-2,4-hexanedione 5,5-Dimethylhydantoin 2,4-Dimethyl-8-hydroxyquinoline 3,4-Dimethyl-8-hydroxyquinoline 2,4-Dimethyl-8-hydroxyquinoline7-sulfonic acid Dimethylhydroxytetracycline 2,4-Dimethylimidazole

5.15(⫹1) 4.70(⫹1) 4.89(⫹1) 4.53(⫹1) 3.95(⫹1) 5.17(⫹1) 4.765(⫹1) 2.0(⫹1)

4.2

1.67

6.273

4.68(⫹1) 3.771 4.217 3.990 3.362 4.41 4.302 9.02(⫹1) 2.77(⫹1) 5.03 3.30(⫹1)

top of rh base of rh

pK2

pK3

pK4

7.39

11.52

8.27 8.21 5.15 2.34

8.31

3.92

5.32

8.12(⫹1) 5.1 11.22 6.63

9.53

7.40

10.16

5.99

9.97

2.146(⫹1) 4.04 3.11(⫹1) 10.60 10.01 9.19 6.20(⫹1) 5.80(⫹1) 3.20 (NH ⫹) 7.5 8.38(⫹1)

9.940(0) 8.09(0)

10.60(0) 10.05(0) 10.14(OH) 9.4

short standard long

DEAN #37261

LEFT

(McGHP)

8.44

INTERACTIVE

top of rh base of rh

SECTION 8

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

Dimethylmalic acid 2,2-Dimethylmalonic acid 3,5-Dimethyl-4-(methylamino) pyridine (20⬚C) 2,3-Dimethylnaphthalene-1-carboxylic acid 2,6-Dimethyl-4-nitrophenol 3,5-Dimethyl-4-nitrophenol ␣,␣-Dimethyloxaloacetic acid 3,3-Dimethylpentanedioic acid 2,2-Dimethylpentanoic acid 4,4-Dimethylpentanoic acid (18⬚C) 2,3-Dimethylphenol 2,4-Dimethylphenol 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol 3,5-Dimethylphenol 2,6-Dimethylphenoxyacetic acid Dimethylphenylsilylacetic acid N,N⬘-Dimethylpiperazine 1,2-Dimethylpiperidine cis-2,6-Dimethylpiperidine 2,2-Dimethylpropanoic acid (pivalic acid) 2,2⬘-Dimethylpropylphosphonic acid 2,4-Dimethylpyridine (2,4-lutidine) 2,5-Dimethylpyridine (2,5-lutidine) 2,6-Dimethylpyridine (2,6-lutidine) 3,4-Dimethylpyridine (3,4-lutidine) 3,5-Dimethylpyridine (3,5-lutidine) 2,4-Dimethylpyridine-1-oxide 2,5-Dimethylpyridine-1-oxide 2,6-Dimethylpyridine-1-oxide 3,4-Dimethylpyridine-1-oxide 3,5-Dimethylpyridine-1-oxide 2,3-Dimethylquinoline 2,6-Dimethylquinoline meso-2,2-Dimethylsuccinic acid rac-2,2-Dimethylsuccinic acid D-2,3-Dimethylsuccinic acid meso-2,3-Dimethylsuccinic acid rac-2,3-Dimethylsuccinic acid 2,4-Dimethylthiazole (␮ ⫽ 0.1) 2,5-Dimethylthiazole (␮ ⫽ 0.1) 4,5-Dimethylthiazole (␮ ⫽ 0.1) N,N-Dimethyl-o-toluidine N,N-Dimethyl-p-toluidine 2,4-Dinitroaniline 2,6-Dinitroaniline 3,5-Dinitroaniline 2,3-Dinitrobenzoic acid

3.17 3.17 9.96(⫹1)

pK2

pK3

pK4

6.06 6.06

3.33 7.190 8.245 1.77 3.70 4.969 4.79 10.50 10.58 10.22 10.59 10.32 10.15 3.356 5.27 4.630(⫹2) 10.22 11.07(⫹1) 5.031 2.84 6.74(⫹1) 6.43(⫹1) 6.71(⫹1) 6.47(⫹1) 6.09(⫹1) 1.627(⫹1) 1.208(⫹1) 1.366(⫹1) 1.493(⫹1) 1.181(⫹1) 4.94(⫹1) 5.46(⫹1) 3.77 3.93 3.82 3.67 3.94 3.98 3.91 3.73 5.86(⫹1) 7.24(⫹1) ⫺4.25(⫹1) ⫺5.23(⫹1) 0.229(⫹1) 1.85

4.62 6.34

8.539(⫹1)

8.65

5.936 6.20 5.93 5.30 6.20

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 2,4-Dinitrobenzoic acid 2,5-Dinitrobenzoic acid 2,6-Dinitrobenzoic acid 3,4-Dinitrobenzoic acid 3,5-Dinitrobenzoic acid 1,1-Dinitrobutane (20⬚C) 1,1-Dinitrodecane 1,1-Dinitroethane (20⬚C) Dinitromethane (20⬚C) 1,1-Dinitropentane 2,4-Dinitrophenol 2,5-Dinitrophenol 2,6-Dinitrophenol 3,4-Dinitrophenol 3,5-Dinitrophenol 2,4-Dinitrophenylacetic acid 1,1-Dinitropropane (20⬚C) 2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid (orotic acid) Diphenylacetic acid Diphenylamine 2,2-Diphenylglutaric acid (20⬚C) 1,3-Diphenylguanidine 2,2-Diphenylheptanedioic acid (20⬚C) 2,2-Diphenylhexanedioic acid (20⬚C) 3,3-Diphenylhexanedioic acid Diphenylhydroxyacetic acid (35⬚C) Diphenylketimine 2,2-Diphenylnonanedioic acid (20⬚C) meso-2,2-Diphenylsuccinic acid rac-2,2-Diphenylsuccinic acid 2,2-Diphenylsuccinic acid, 1methyl ester (20⬚C) 2,2-Diphenylsuccinic acid, 4methyl ester (20⬚C) Diphenylthiocarbazone Dipropylamine Dipropylenetriamine 2,2-Dipropylglutaric acid Dipropylmalonic acid 2,2⬘-Dipyridyl 2,3⬘-Dipyridyl (20⬚C) 2,4⬘-Dipyridyl (20⬚C) 3,3⬘-Dipyridyl (20⬚C, ␮ ⫽ 0.2) 3.4⬘-Dipyridyl (20⬚C, ␮ ⫽ 0.2) 4,4⬘-Dipyridyl Dithiodiacetic acid (18⬚C) 1,4-Dithioerythritol

pK1 1.43 1.62 1.14 2.82 2.85 5.90 3.60 5.21 3.60 5.337 4.08 5.216 3.713 5.424 6.732 3.50 5.5 1.8(⫹1)

3.939 0.9(⫹1) 3.91 10.12 4.28

pK2

pK3

pK4

9.55(0)

5.38 5.39

4.17

5.40

4.22 3.05

5.19

6.82 4.33

top of rh base of rh

5.38

3.48 3.58 4.47 3.900 4.50 10.91(⫹1) 7.72(⫹3) 3.688 2.04 ⫺0.52(⫹2) 1.52(⫹2) 1.19(⫹2) 3.0(⫹2) 3.0(⫹2) 3.17(⫹2) 3.075 9.5

15 9.56(⫹2) 7.31 7.51 4.352(⫹1) 4.42(⫹1) 4.77(⫹1) 4.60(⫹1) 4.85(⫹1) 4.82(⫹1) 4.201

10.65(⫹1)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

Dithiooxamide (rubeanic acid) Dulcitol

10.89 13.46

Ecgonine Emetine Epinephrine enantiomorph Epinephrine, pseudo Ergometrinine Ergonovine Eriochrome Black T 1,2-Ethanediamine Ethane-1,2-diamino-N,N⬘-dimethylN,N⬘-diacetic acid (20⬚C) 1,2-Ethanedithiol Ethanethiol (␮ ⫽ 0.015) Ethoxyacetic acid (18⬚C) 2-Ethoxyaniline (o-phenetidine) 3-Ethoxyaniline 4-Ethoxyaniline 2-Ethoxybenzoic acid (20⬚C) 3-Ethoxybenzoic acid (20⬚C) 4-Ethoxybenzoic acid (20⬚C) Ethoxycarbonylethylamine 2-Ethoxyethanethiol 2-Ethoxyethylamine 2-Ethoxyphenol 3-Ethoxyphenol (4-Ethoxyphenyl)phosphonic acid 4-Ethoxypyridine Ethyl acetoacetate 3-Ethylacrylic acid N-Ethylalanine Ethylamine (3-Ethylamino)phenylphosphonic acid N-Ethylaniline 2-Ethylaniline 3-Ethylaniline 4-Ethylaniline Ethylarsonic acid (18⬚C) Ethylbarbituric acid 2-Ethylbenzimidazole (␮ ⫽ 0.16) 2-Ethylbenzoic acid 4-Ethylbenzoic acid Ethylbiguanide 2-Ethylbutanoic acid (20⬚C) S-Ethyl-L-cysteine (␮ ⫽ 0.1) Ethylenebiguanide (30⬚C) Ethylenebis(thioacetic acid) (18⬚C) Ethylenediamine-N,N⬘-diacetic acid Ethylenediamine-N,N-dimethylN⬘,N⬘-diacetic acid Ethylenediamine-N,N-dipropanoic acid (30⬚C)

10.91 7.36(⫹1) 9.39(⫹1) 9.53(⫹1) 7.32(⫹1) 6.73(⫹1) 6.3 6.85(⫹2) 6.047(0) 8.96 10.61 3.65 4.47(⫹1) 4.17(⫹1) 5.25(⫹1) 4.21 4.17 4.80 9.13(⫹1) 9.38 6.26(⫹1) 10.109 9.655 2.06 6.67(⫹1) 10.68 4.695 2.22(⫹1) 10.63(⫹1) 1.1(⫹1) 5.11(⫹1) 4.42(⫹1) 4.70(⫹1) 5.00(⫹1) 3.89 3.69(⫹1) 6.27(⫹1) 3.79 4.35 2.09(⫹1) 4.710 2.03(⫹1) 1.74 3.382(0) 6.42 6.047 6.87

pK2

pK3

pK4

8.23(0)

11.55 9.92(⫹1) 10.068(⫺1) 10.54

7.28

10.22(0) 4.90(0)

7.24(⫺1)

8.35

11.47(0) 8.60(0) 2.88 4.352(⫺1) 9.46 10.068 9.60

11.34

11.76

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance Ethylenediamine-N,N,N⬘,N⬘-tetraacetic acid (␮ ⫽ 0.1) Ethylenediamine-N,N,N⬘,N⬘-tetrapropanoic acid (30⬚C) Ethylene glycol Ethyleneimine cis-Ethylene oxide dicarboxylic acid trans-Ethylene oxide dicarboxylic acid N-Ethylethylenediamine N-Ethylglycine (␮ ⫽ 0.1) 3-Ethylglutaric acid Ethyl hydroperoxide Ethyl hydrogen malonate 3-Ethyl-2-hydroxypyridine Ethylmalonic acid N-Ethyl mercaptoacetamide Ethyl 2-mercaptoacetate Ethyl 3-mercaptopropanoate 3-Ethyl-4-(methylamino)pyridine (20⬚C) 5-Ethyl-5-(1-methylbutyl)barbituric acid Ethyl methyl ketoxime Ethylmethylmalonic acid 1-Ethyl-2-methylpiperidine 3-Ethyl-6-methylpyridine (20⬚C) 3-Ethyl-4-methylpyridine-1-oxide 5-Ethyl-2-methylpyridine-1-oxide 1-Ethyl-2-methyl-2-pyrroline Ethylmorphine (15⬚C) Ethyl nitroacetate 3-Ethylpentane-2,4-dione 2-Ethylpentanoic acid (18⬚C) 5-Ethyl-5-pentylbarbituric acid 2-Ethylphenol 3-Ethylphenol 4-Ethylphenol 4-Ethylphenylacetic acid 5-Ethyl-5-phenylbarbituric acid Ethylphosphinic acid Ethylphosphonic acid 1-Ethylpiperidine (␮ ⫽ 0.01) 2,2-Ethylpropylglutaric acid Ethylpropylmalonic acid 2-Ethylpyridine 3-Ethylpyridine (20⬚C) 4-Ethylpyridine Ethyl 3-pyridinecarboxylate Ethyl 4-pyridinecarboxylate 2-Ethylpyridine-1-oxide 3-Ethylpyridine-1-oxide Ethylpyrrolidine

pK1

pK2

pK3

pK4

1.99

2.67

6.16

10.26

3.00

3.43

6.77

9.60

14.22 8.04(⫹1) 1.93 1.93 7.63(⫹2) 2.34(⫹1) 4.28 11.80 3.55 5.00(⫹1) 2.90(0) 8.14(SH) 7.95(SH) 9.48(SH) 9.90(⫹1)

top of rh base of rh

3.92 3.25 10.56(⫹1) 10.23(0) 5.33

5.55(⫺1)

8.11(0) 12.45 2.86(0) 10.66(⫹1) 6.51(⫹1) ⫺1.534(⫹1) ⫺1.288(⫹1) 11.84(⫹1) 8.08 5.85 11.34 4.71 7.960 10.2 10.07 10.0 4.373 7.445 3.29 2.43 10.45(⫹1) 3.511 3.14 5.89(⫹1) 5.80(⫹1) 5.87(⫹1) 3.35(⫹1) 3.45(⫹1) ⫺1.19(⫹1) ⫺0.965(⫹1) 10.43(⫹1)

6.41(⫺1)

8.05

7.43

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 2-Ethyl-2-pyrroline Ethylsuccinic acid S-Ethylthioacetic acid N-Ethyl-o-toluidine N-Ethylveratramine ␤-Eucaine Fluoroacetic acid 2-Fluoroacrylic acid 2-Fluoroaniline 3-Fluoroaniline 4-Fluoroaniline 2-Fluorobenzoic acid 3-Fluorobenzoic acid 4-Fluorobenzoic acid Fluoromandelic acid 2-Fluorophenol 3-Fluorophenol 4-Fluorophenol 2-Fluorophenoxyacetic acid 3-Fluorophenoxyacetic acid 4-Fluorophenoxyacetic acid 4-Fluorophenylacetic acid 2⬘-Fluorophenylalanine 3⬘-Fluorophenylalanine 4-Fluorophenylalanine 2-Fluorophenylphosphonic acid 3-Fluorophenylselenic acid 4-Fluorophenylselenic acid 2-Fluoropyridine 3-Fluoropyridine 5-Fluorouracil Folic acid (pteroylglutamic acid) Formic acid N-Formylglycine 2-Formyl-3-hydroxypyridine (20⬚C) 4-Formyl-3-hydroxypyridine 2-Formyl-3-methoxypyridine (20⬚C) Formyl-3-methoxypyridine (20⬚C) D-(⫺)-Fructose Fumaric acid 2-Furancarboxylic acid (2-furoic acid) D-(⫹)-Galactose

Galactose-1-phosphoric acid Glucoascorbic acid D-Gluconic acid ␣-D-(⫹)-Glucose ␣-D-Glucose-1-phosphate trans-Glutaconic acid D-(⫺)-Glutamic acid L-Glutamic acid

pK1

pK2

pK3

pK4

7.87(⫹1) 4.08(0) 5.06 4.92(⫹1) 7.40(⫹1) 9.35(⫹1) 2.586 2.55 3.20(⫹1) 3.58(⫹1) 4.65(⫹1) 3.27 3.865 4.14 4.244 8.73 9.29 9.89 3.08 3.08 3.13 4.25 2.14(⫹1) 2.10(⫹1) 2.13(⫹1) 1.64 4.34 4.50 ⫺0.44(⫹1) 2.97(⫹1) 8.00(0) 8.26 3.751 3.43 3.40(⫹1) 4.05(⫹1) 3.89(⫹1) 4.45(⫹1) 12.03 3.10 3.164 12.35 1.00 4.26 3.86 12.28 1.11(0) 3.77 2.162(⫹1) 2.19(⫹1)

9.01(0) 8.98(0) 9.05(0) 6.80

ca 13(⫺1)

6.95(OH) 6.77(OH) 12.95 11.7 4.60

6.17 11.58

6.504(⫺1) 5.08 4.272(0) 4.25(0)

9.358(⫺1) 9.67(⫺1)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

Glutamic acid, 1-ethyl ester Glutamic acid, 5-ethyl ester L-Glutamine (␮ ⫽ 0.2) Glutaric acid Glutaric acid monoamide Glutarimide Glutathione DL-Glyceric acid Glycerol Glyceryl-1-phosphoric acid Glyceryl-2-phosphoric acid Glycine Glycine amide Glycine, ethyl ester Glycine hydroxamic acid Glycine, methyl ester Glycine-O-phenylphosphorylserine Glycolic acid N-Glycl-␣-alanine Glycylalanylalanine N-Glycylasparagine Glycyclaspartic acid Glycyl-DL-glutamine (18⬚C) N-Glycylglycine Glycylglycylcysteine (35⬚C) Glycylglycylglycine Glycyl-L-histidine (␮ ⫽ 0.16) Glycylisoleucine N-Glycyl-L-leucine Glycyl-O-phosphorylserine L-Glycylproline (␮ ⫽ 0.1) N-Glycylsarcosine (␮ ⫽ 0.1) N-Glycylserine Glycylserylglycine Glycyltyrosine Glycylvaline Glyoxaline Glyoxylic acid Guanidineacetic acid Guanine Guanine deoxyriboside-3⬘-phosphoric acid Guanosine Guanosine-5⬘-diphosphoric acid (␮ ⫽ 0.1; pK 5 9.6) Guanosine-3⬘-phosphoric acid Guanosine-5⬘-phosphoric acid (␮ ⫽ 0.1) Guanosine-5⬘-triphosphoric acid [␮ ⫽ 0.1; pK 5 7.10(⫺3); pK 6 9.3(⫺4)] Guanylurea Harmine (20⬚C) Heptafluorobutanoic acid

3.85(⫹1) 2.15(⫹1) 2.17(⫹1) 3.77 4.600(0) 11.43 2.12(⫹1) 3.64 14.15 — 1.335(0) 2.341(⫹1) 8.03(⫹1) 7.66(⫹1) 7.10 7.59(⫹1) 2.96 3.831 3.15(⫹1) 3.38(⫹1) 2.942 2.81(⫹1) 2.88(⫹1) 3.126(⫹1) 2.71 3.225(⫹1) 6.79 8.00 3.180(⫹1) 2.90 2.81(⫹1) 2.98(⫹1) 2.98(+1) 3.32 2.93 3.15 7.03(⫹1) 3.30(0) 2.82(⫹1) 3.3(⫹1) —

pK2

pK3

pK4

7.84(0) 9.19(0) 9.13(0) 6.08

3.53(0)

8.66

9.12

6.656(⫺1) 6.650(⫺1) 9.60(0)

9.10 8.07 8.33(0) 8.10(0) 4.45(0) 8.33(0) 8.252(0) 2.71 8.090(0) 8.20 8.327(0) 6.02 8.65(0) 8.55(0) 8.38(0) 7.99 8.45 8.18

8.60(⫺1)

7.94

7.94

8.43

10.49

9.2 2.9

12.3 6.4

9.7

1.9(⫹1) —

9.25(0) —

12.33(OH) 2.9

6.3

0.7 —

2.3 2.4

—

1.80 7.61(⫹1) 0.17

top of rh base of rh

5.92 6.1 —

8.20

—

9.38 9.4 3.0(⫺2)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 4,4,5,5,6,6,6-Heptafluorohexanoic acid 4,4,5,5,6,6,6-Heptafluoro-2-hexenoic acid Heptanedioic acid (pimelic acid) 2,4-Heptanedione Heptanoic acid Heroin 2,4-Hexadienoic acid (sorbic acid) 1,1,1,3,3,3-Hexafluoro-2,2-propanediol 1,1,1,3,3,3-Hexafluoro-2-propanol Hexahydroazepine Hexamethyldisilazine 1,2,3,8,9,10-Hexamethyl-4,7-phenanthroline (20⬚C) 1,6-Hexanediamine 1,6-Hexanedioic acid 2,4-Hexanedione 2,2⬘,4,4⬘,6,6⬘-Hexanitrodiphenylamine Hexanoic acid (20⬚C) trans-2-Hexenoic acid trans-3-Hexenoic acid 3-Hexen-4-oic acid 4-Hexen-5-oic acid Hexylamine Hexylarsonic acid Hexylphosphonic acid DL-Histidine Histidine amide (␮ ⫽ 0.2) Histidine, methyl ester (␮ ⫽ 0.1) Histidylglycine Histidylhistidine (␮ ⫽ 0.16) DI-Homatropine DI-Homocysteine Homocysteine (␮ ⫽ 0.1) Hydantoin Hydrastine Hydrazine-N,N-diacetic acid Hydrazine-N⬘-N⬘-diacetic acid 4-Hydrazinocarbonylpyridine (20⬚C) N-Hydroxyacetamide 2⬘-Hydroxyacetophenone 3⬘-Hydroxyacetophenone 4⬘-Hydroxyacetophenone 1-Hydroxyacridine (15⬚C) 2-Hydroxyacridine (15⬚C) 3-Hydroxyacridine (15⬚C)

pK1

pK2

pK3

pK4

4.18 3.23 4.484 8.43(keto); 9.15(enol) 4.893 7.6(⫹1) 4.77 8.801

5.424

9.42 11.07 7.55 7.26 9.830(⫹2) 4.418 8.49 (enol); 9.32 (keto) 5.42(⫹1) 4.849 4.74 4.72 4.58 4.74 10.64(⫹1) 4.16 2.6 1.82(⫹2) 5.78(⫹2) 5.01(⫹2) 2.40(⫹2) 5.40(⫹2) 9.7(⫹1) 2.222(⫹1) 1.593(⫹2) 9.12 6.23(⫹1) ⬍0.1 2.40 1.82 9.40 9.90 9.19 8.05 5.72 5.62 5.30

10.930(⫹1) 5.412

9.19 7.9 6.00(⫹1) 7.64(⫹1) 7.23(⫹1) 5.80(⫹1) 6.80(⫹1)

7.82(0) 7.95(0)

8.87 2.523(⫹1)

10.86 8.676(0)

2.8 3.12 3.52

3.8 7.32 10.79

9.16(0)

9.413(⫺1)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

␣-Hydroxyasparagine ␤-Hydroxyasparagine Hydroxyaspartic acid 2-Hydroxybenzaldehyde (salicylaldehyde) 3-Hydroxybenzaldehyde 4-Hydroxybenzaldehyde 2-Hydroxybenzaldehyde oxime 2-Hydroxybenzamide 2-Hydroxybenzenemethanol (2-hydroxybenzyl alcohol) 3-Hydroxybenzenemethanol 4-Hydroxybenzenemethanol 4-Hydroxybenzenesulfonic acid 2-Hydroxybenzohydroxamic acid 2-Hydroxybenzoic acid (salicyclic acid) 3-Hydroxybenzoic acid 4-Hydroxybenzoic acid 4-Hydroxybenzonitrile 2-Hydroxy-5-bromobenzoic acid 2-Hydroxybutanoic acid (30⬚C) L-3-Hydroxybutanoic acid (30⬚C) 4-Hydroxybutanoic acid (30⬚C) 2-Hydroxy-5-chlorobenzoic acid trans-2⬘-Hydroxycinnamic acid trans-3⬘-Hydroxycinnamic acid 10-Hydroxycodeine cis-2-Hydroxycyclohexane-1-carboxylic acid trans-2-Hydroxycyclohexane-1carboxylic acid cis-3-Hydroxycyclohexane-1-carboxylic acid trans-3-Hydroxycyclohexane-1carboxylic acid cis-4-Hydroxycyclohexane-1-carboxylic acid trans-4-Hydroxycyclohexane-1carboxylic acid 1-Hydroxy-2,4-dihydroxymethylbenzene N-(Hydroxyethyl)biguanide N-(2-Hydroxyethyl)ethylenediamine N⬘-(2-Hydroxyethyl)ethylenediamine-N,N,N⬘-triacetic acid N-(2-Hydroxyethyl)iminodiacetic acid (␮ ⫽ 0.1) N-(2-Hydroxyethyl)piperazine-N⬘ethansulfonic acid (20⬚C) 4⬘-(2-Hydroxyethyl)-1⬘-piperazinepropanesulfonic acid (20⬚C)

2.28(⫹1) 2.09(⫹1) 1.91(⫹1) 8.34

pK2 7.20(0) 8.29(0) 3.51(0)

9.00 7.620 1.37(⫹1) 8.36 9.92

9.18

9.83 9.82 — 5.19 2.98

9.055(⫺1)

4.076 4.582 7.95 2.61 3.65 4.41 4.71 2.63 4.614 4.40 7.12 4.796

top of rh base of rh

pK3

pK4

9.11(⫺1)

12.11

12.38 9.85 9.23

4.682 4.602 4.815 4.836 4.687 9.79 2.8(⫹2) 7.21(⫹2)

11.53(⫹1) 10.12(⫹1)

2.39

5.37

2.2

8.65

9.93

7.55 8.00

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

2-Hydroxyethyltrimethylamine L-␤-Hydroxyglutamic acid 1-Hydroxy-4-hydroxymethylbenzene 5-Hydroxy-2-(hydroxymethyl)-4Hpyran-4-one 3-Hydroxy-2-hydroxymethylpyridine (20⬚C, ␮ ⫽ 0.2) 3-Hydroxy-4-hydroxymethylpyridine (20⬚C, ␮ ⫽ 0.2) 8-Hydroxy-7-iodoquinoline-5-sulfonic acid Hydroxylysine (38⬚C, ␮ ⫽ 0.1) 2-Hydroxy-3-methoxybenzaldehyde 3-Hydroxy-4-methoxybenzaldehyde (isovanillin) 4-Hydroxy-3-methoxybenzaldehyde (vanillin) 4-Hydroxy-3-methoxybenzoic acid 1-Hydroxy-2-methoxybenzylamine 2-Hydroxy-1-methoxybenzylamine 3-Hydroxy-2-methoxybenzylamine 2-Hydroxymethyl-2-benzeneacetic acid (2-Hydroxy-5-methylbenzene)methanol 2-Hydroxy-3-methylbenzoic acid 2-Hydroxy-4-methylbenzoic acid 2-Hydroxy-5-methylbenzoic acid 2-Hydroxy-6-methylbenzoic acid 2-Hydroxy-2-methylbutanoic acid (18⬚C) 3-Hydroxy-2-methylbutanoic acid (18⬚C) 4-Hydroxy-4-methylpentanoic acid (18⬚C) 1-Hydroxymethylphenol Hydroxymethylphosphoric acid 2-Hydroxy-2-methylpropanoic acid (␮ ⫽ 0.1) 2-Hydroxy-4-methylpyridine 8-Hydroxy-2-methylquinoline 8-Hydroxy-4-methylquinoline 8-Hydroxy-2-methylquinoline-5sulfonic acid 8-Hydroxy-4-methylquinoline-7sulfonic acid 8-Hydroxy-6-methylquinoline-5sulfonic acid 2-Hydroxy-1-naphthoic acid (20⬚C) 2-Hydroxy-2-nitrobenzoic acid 2-Hydroxy-3-nitrobenzoic acid

8.94(⫹1) 2.09 9.84

pK2

4.18

7.90

8.03

5.00(⫹1)

9.07(OH)

5.00(⫹1)

8.95(OH)

2.51(0)

7.417(⫺1)

2.13(⫹2) 7.912

8.62(⫹1)

pK3

pK4

9.20

9.67(0)

8.889 7.396 4.355 8.70(⫹1) 8.89(⫹1) 8.94(⫹1) 4.12

10.52(0) 10.52(0) 10.42(0)

10.15 2.99 3.17 4.08 3.32 3.991 4.648 4.873 9.95 1.91 3.717

7.15

4.529(⫹1) 5.55(⫹1) 5.56(⫹1) 4.80(0)

10.31(0) 10.00(0) 9.30(⫺1)

4.78(0)

10.01(⫺1)

4.20(0)

8.7(⫺1)

3.29 2.23 1.87

9.68

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

pK2

2-Hydroxy-5-nitrobenzoic acid 2-Hydroxy-6-nitrobenzoic acid 2-Hydroxy-4-nitrophenylphosphonic acid 8-Hydroxy-7-nitroquinoline-5-sulfonic acid 3-Hydroxy-4-nitrotoluene (␮ ⫽ 0.1) 4-Hydroxypentanoic acid (18⬚C) 4-Hydroxy-3-pentenoic acid 3-Hydroxyphenazine (15⬚C) 4-Hydroxyphenylarsonic acid

2.12 2.24 1.22

5.39

1.94(0)

5.750(⫺1)

3-Hydroxyphenylboric acid 2-Hydroxy-2-phenylpropanoic acid 2-(2-Hydroxyphenyl)pyridine (20⬚C) trans-4-Hydroxyproline Hydroxypropanedioic acid (tartronic acid) 2-Hydroxypropanoic acid 1-Hydroxy-2-propylbenzene 4-Hydroxypteridine 2-Hydroxypyridine 3-Hydroxypyridine 4-Hydroxypyridine 2-Hydroxypyridine-N-oxide 2-Hydroxypyrimidine 4-Hydroxypyrimidine 8-Hydroxyquinazoline 2-Hydroxyquinoline (20⬚C) 3-Hydroxyquinoline (20⬚C) 4-Hydroxyquinoline (20⬚C) 5-Hydroxyquinoline (20⬚C) 6-Hydroxyquinoline (20⬚C) 7-Hydroxyquinoline (20⬚C) 8-Hydroxyquinoline (20⬚C) 8-Hydroxyquinoline-5-sulfonic acid DL-Hydroxysuccinic acid (malic acid) L-Hydroxysuccinic acid Hydroxytetracycline 5-Hydroxy-1,2,3,4-tetrazole 4-Hydroxy-3-(2⬘-thiazolyazo)toluene 2-Hydroxytoluene 3-Hydroxytoluene 4-Hydroxytoluene 4-Hydroxy-␣,␣,␣-trifluorotoluene 1-Hydroxy-2,4,6-trihydroxymethylbenzene Hydroxyuracil

8.55 3.532 4.19(⫹1)

top of rh base of rh

pK3

pK4

7.41 4.686 4.30 2.67 3.89

8.37 (phenol) 10.84

10.05

10.64

1.818(⫹1) 2.37

9.662(0) 4.74

3.858 10.50 1.3(⫹1) 1.25(⫹1) 4.80(⫹1) 3.23(⫹1) ⫺0.62(⫹1) 2.24(⫹1) 1.85(⫹1) 3.41(⫹1) ⫺0.31(⫹1) 4.30(⫹1) 2.27(⫹1) 5.20(⫹1) 5.17(⫹1) 5.48(⫹1) 4.91(⫹1) 4.092(⫹1)

7.89(0) 11.62(0) 8.72(0) 11.09(0) 5.97(0) 9.17(0) 8.59(0) 8.65(0) 11.74 8.06(0) 11.25(0) 8.54(0) 8.88(0) 8.85(0) 9.81(0) 8.776(0)

3.458

5.097

3.40 3.27(⫹1) 3.32 8.36

5.05 7.32(0)

9.11(⫺1)

10.33 10.10 10.276 8.675 9.56 8.64

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

pK2

pK3

Hydroxyvaline Hyoscyamine Hypoxanthene Hypoxanthine

2.55(⫹1) 9.68(⫹1) 1.79(⫹1) 5.3

9.77(0)

Imidazole Imidazolidinetrione (parabanic acid) 4-(4-Imidazolyl)butanoic acid (␮ ⫽ 0.1) 2-(4-Imidazolyl)ethylamine 3-(4-Imidazolyl)propanoic acid (␮ ⫽ 0.16) 3,3⬘-Iminobispropanoic acid 3,3⬘-Iminobispropylamine (30⬚C) 2,2⬘-Iminodiacetic acid (diglycine) (30⬚C, ␮ ⫽ 0.1) 4-Indanol Indole-3-acetic acid Inosine Inosine-5⬘-phosphoric acid Inosine-5⬘-triphosphoric acid [pK 5 7.68(⫺4)] Iodoacetic acid 2-Iodoaniline 3-Iodoaniline 4-Iodoaniline 2-Iodobenzoic acid 3-Iodobenzoic acid 4-Iodobenzoic acid 5-Iodohistamine

6.993(⫹1) 6.10

10.58(0)

4.26(⫹1)

7.26(0)

5.784(⫹2) 3.96(⫹1)

9.756(⫹1) 7.57(0)

4.11(0) 8.02(⫹2) 2.54(0)

9.61(⫺1) 9.70(⫹1) 9.12(⫺1)

10.32 4.75 ca 1.5(⫹1) 1.54(0) —

8.96(0) 6.66(⫺1) —

12.36

9.20(⫹1) (NH⫹3 ) 7.417

11.88(0) (imino)

7-Iodo-8-hydroxyquinoline-5-sulfonic acid Iodomandelic acid Iodomethylphosphoric acid 2-Iodophenol 3-Iodophenol 4-Iodophenol 2-Iodophenoxyacetic acid 3-Iodophenoxyacetic acid 4-Iodophenoxyacetic acid 2-Iodophenylacetic acid 3-Iodophenylacetic acid 4-Iodophenylacetic acid 2-Iodophenylphosphoric acid 2-Iodopropanoic acid 3-Iodopropanoic acid 2-Iodopyridine 3-Iodopyridine 4-Iodopyridine (20⬚C) Isoasparagine

3.175 2.54(⫹1) 3.58(⫹1) 3.82(⫹1) 2.86 3.86 4.00 4.06(⫹1) (imidazole) 2.514 3.264 1.30 8.464 8.879 9.200 3.17 3.13 3.16 4.038 4.159 4.178 1.74 3.11 4.08 1.82(⫹1) 3.25(⫹1) 4.02(⫹1) 2.97(⫹1)

8.91(0)

pK4

12.07(⫺1)

10.70(0)

2.2(⫺2)

6.92(⫺3)

6.72

7.06

8.02(0)

short standard long

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(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.55

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

Isobutylacetic acid (18⬚C) Isobutylamine Isochlorotetracycline Isocreatine Isogluatamine Isohistamine (␮ ⫽ 0.1) L-Isoleucine Isolysergic acid Isopilocarpine (15⬚C) 2-(Isopropoxy)benzoic acid (20⬚C) 3-(Isopropoxy)benzoic acid (20⬚C) 4-(Isopropoxy)benzoic acid (20⬚C) Isopropylamine N-Isopropylaniline 5-Isopropylbarbituric acid 2-Isopropylbenzene acid 4-Isopropylbenzene acid N-Isopropylglycine (␮ ⫽ 0.1) Isopropylmalonic acid Isopropylmalonic acid mononitrile 3-Isopropyl-4-(methylamino)pyridine (20⬚C) 3-Isopropylpentanedioic acid 4-Isopropylphenylacetic acid Isopropylphosphinic acid Isopropylphosphonic acid 2-Isopropylpyridine 3-Isopropylpyridine (20⬚C) 4-Isopropylpyridine DL-Isoproterenol Isoquinoline Isoretronecanol L-Isoserine (␮ ⫽ 0.16) Isothiocyanatoacetic acid

4.79 10.41(⫹1) 3.1(⫹1) 2.84(⫹1) 3.81(⫹1) 6.036(⫹2) 2.35(⫹1) 3.33(0) 7.18(⫹1) 4.24 4.15 4.68 10.64(⫹1) 5.50(⫹1) 4.907(⫹1) 3.64 4.36 2.36(⫹1) 2.94 2.401 9.96(⫹1)

L-(⫹)-Lactic

acid

L-Leucine

Leucine amide Leucine, ethyl ester (␮ ⫽ 0.1) L-Leucyl-L-asparagine L-Leucyl-L-glutamine DL-Leucylglycine Leucylisoserine (20⬚C) D-Leucyl-L-tyrosine L-Leucyl-L-tyrosine Lysergic acid L-(⫹)-Lysine Lysine, methyl ester (␮ ⫽ 0.1) L-Lysyl-L-alanine L-Lysyl-D-alanine Lysylglutamic acid L-Lysyl-L-lysine (␮ ⫽ 0.1)

4.30 4.391 3.56 2.66 5.83(⫹1) 5.72(⫹1) 6.02(⫹1) 8.64(⫹1) 5.40(⫹1) 10.83 2.72(⫹1) 6.62 3.858 2.33(⫹1) 7.80(⫹1) 7.57(⫹1) 3.00(⫹1) 2.99(⫹1) 3.25(⫹1) 3.188(⫹1) 3.12(⫹1) 3.46(⫹1) 3.44(⫹1) 2.18(⫹2) 6.965(⫹1) 3.22(⫹1) 3.00(⫹1) 2.93(⫹2) 3.01(⫹2)

pK2

6.7(0)

top of rh base of rh

pK3

pK4

8.3(⫺1)

7.88(0) 9.274(⫹1) 9.68(0) 8.46(NH)

10.06(0) 5.88

5.51

8.44

9.25(0)

9.60(0)

8.12(0) 8.11(0) 8.28(0) 8.207(0) 8.38(0) 7.84(0) 7.68(0) 8.94(⫹1) 10.251(0) 7.62(0) 7.74(0) 4.47(⫹1) 7.53(⫹1)

10.35(⫺1) 10.09(⫺1) 10.53(0) 10.70(⫺1) 10.63(⫺1) 7.75(0) 10.05(0)

10.50(⫹1) 10.01(⫺1)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

pK2

(␮ ⫽ 0.1) (␮ ⫽ 0.1) L-Lysyl-D-lysyl-L-lysine (␮ ⫽ 0.1) L-Lysyl-D-lysyl-lysine (␮ ⫽ 0.1) ␣-D-Lyxose

2.85(⫹2) 3.08(⫹2) 2.91(⫹2) 2.94(⫹2) 12.11

7.53(⫹1) 7.34(⫹1) 7.29(⫹1) 7.15(⫹1)

Maleic acid Malonamic acid Malonic acid Malonitrile (cyanoacetic acid) Mandelic acid D-(⫹)-Mannose Mercaptoacetic acid (thioglycolic acid) 2-Mercaptobenzoic acid (20⬚C) 2-Mercaptobutanoic acid Mercaptodiacetic acid 2-Mercaptoethanesulfonic acid (20⬚C) 2-Mercaptoethanol 2-Mercaptoethylamine 2-Mercaptohistidine Mercapto-S-phenylacetic acid (␮ ⫽ 0.1) 2-Mercaptopropane (␮ ⫽ 0.1) 3-Mercapto-1,2-propanediol (␮ ⫽ 0.5) 2-Mercaptopropanoic acid 3-Mercaptopropanoic acid 2-Mercaptopyridine (20⬚C) 3-Mercaptopyridine (20⬚C) 4-Mercaptopyridine (20⬚C) 2-Mercaptoquinoline (20⬚C) 3-Mercaptoquinoline (20⬚C) 4-Mercaptoquinoline (20⬚C) Mercaptosuccinic acid Mesitylenic acid Mesoxaldialdehyde Methacrylic acid Methanethiol DL-Methionine 2-(N-Methoxyacetamido)pyridine 3-(N-Methoxyacetamido)pyridine 4-(N-Methoxyacetamido)pyridine Methoxyacetic acid 3-Methoxy-D-␣-alanine 2-Methoxyaniline 3-Methoxyaniline 4-Methoxyaniline 2-Methoxybenzoic acid 3-Methoxybenzoic acid 4-Methoxybenzoic acid N,N-Methoxybenzylamine

1.910 3.641(0) 2.826 2.460 3.411 12.08 3.60(0)

6.33

L-Lysyl-D-lysine

L-Lysyl-L-lysyl-L-lysine

4.05(0) 3.53(0) 3.32

9.88 8.27(⫹1) 1.84(⫹1) 3.9

pK3 9.92(0) 9.80(0) 9.79(0) 9.60(0)

pK4 10.89(⫺1) 10.54(⫺1) 10.54(⫺1) 10.38(⫺1)

5.696

10.56(SH)

4.29 9.5(⫺1)

10.53(0) 8.47(0)

11.4(SH)

10.20(SH) 10.84(SH) 10.00(0) 7.03(0) 8.86(0) 10.21(0) 6.13(0) 8.83(0) 4.94(⫺1)

10.94(SH)

10.86 9.43 4.32(0) — ⫺1.07(⫹1) 2.26(⫹1) 1.43(⫹1) ⫺1.44(⫹1) 2.33(⫹1) 0.77(⫹1) 3.30(0) 4.32 3.60 4.66 10.70 2.28(⫹1) 2.01(⫹1) 3.52(⫹1) 4.62(⫹1) 3.570 2.037(⫹1) 4.53(⫹1) 4.20(⫹1) 5.36(⫹1) 4.09 4.08 4.49 9.68(⫹1)

9.21(0)

9.176(0)

short standard long

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

2-Methoxycarbonylaniline 3-Methoxycarbonylaniline 4-Methoxycarbonylaniline Methoxycarbonylmethylamine 2-Methoxycarbonylpyridine 3-Methoxycarbonylpyridine 4-Methoxycarbonylpyridine trans-2-Methoxycinnamic acid trans-3-Methoxycinnamic acid trans-4-Methoxycinnamic acid 2-Methoxyethylamine 2-Methoxy-4-nitrophenylphosphonic acid 2-Methoxyphenol 3-Methoxyphenol 4-Methoxyphenol (2⬘-Methoxy)phenoxyacetic acid (3⬘-Methoxy)phenoxyacetic acid (4⬘-Methoxy)phenoxyacetic acid 4⬘-Methoxyphenylacetic acid (4-Methoxyphenyl)phosphinic acid (17⬚C) (2-Methoxyphenyl)phosphonic acid (4-Methoxyphenyl)phosphonic acid (17⬚C) 3-(2⬘-Methoxyphenyl)propanoic acid 3-(3⬘-Methoxyphenyl)propanoic acid 3-(4⬘-Methoxyphenyl)propanoic acid 3-Methoxyphenylselenic acid 4-Methoxyphenylselenic acid 2-Methoxy-4-(2-propenyl)phenol 2-Methoxypyridine 3-Methoxypyridine 4-Methoxypyridine 4-Methoxy-2-(2⬘-thiazoylazo)phenol 2-Methylacrylic acid (18⬚C) N-Methylalanine O-Methylallothreonine (␮ ⫽ 0.1) Methylamine 2-(N-Methylamino)benzoic acid 3-(N-Methylamino)benzoic acid 4-(N-Methylamino)benzoic acid Methylaminodiacetic acid (20⬚C) 2-(Methylamino)ethanol 2-(2-Methylaminoethyl)pyridine (30⬚C) 2-(Methylaminomethyl)6-methylpyridine (␮ ⫽ 0.5) 2-(Methylaminomethyl)pyridine (30⬚C)

2.23(⫹1) 3.64(⫹1) 2.38(⫹1) 7.66(⫹1) 2.21(⫹1) 3.13(⫹1) 3.26(⫹1) 4.462 4.376 4.539 9.45(+1) 1.53

pK2

top of rh base of rh

pK3

pK4

6.96

9.99 9.652 10.20 3.231 3.141 3.213 4.358 2.35 2.16 2.4

7.77 7.15

4.804 4.654 4.689 4.65 5.05 10.0 3.06(⫹1) 4.91(⫹1) 6.47(⫹1) 7.83 4.66 2.22(⫹1) 1.92(+1) 10.62(⫹1) 1.93(⫹1) — — 2.146 9.88(⫹1) 3.58(⫹2)

10.19(0) 8.90(0) 5.34(0) 5.10(0) 5.05 10.088 9.65(⫹1)

3.03(⫹2)

9.15(⫹1)

2.92(⫹2)

8.82(⫹1)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

4-Methylamino-3-methylpyridine (20⬚C) (3-Methylamino)phenylphosphonic acid (4-Methylamino)phenylphosphonic acid 3-(Methylamino)pyridine (30⬚C) 4-(Methylamino)pyridine (20⬚C) 4-(Methylamino)-2,3,5,6-tetramethylpyridine (20⬚C) N-Methylaniline Methylarsonic acid (18⬚C) 1-Methylbarbituric acid 5-Methylbarbituric acid 2-(N-Methylbenzamido)pyridine 3-(N-Methylbenzamido)pyridine 4-(N-Methylbenzamido)pyridine 2-Methylbenzimidazole (␮ ⫽ 0.16) 2-Methylbenzoic acid (o-toluic acid) 3-Methylbenzoic acid 4-Methylbenzoic acid N-Methyl-1-benzoylecgonine Methylbiguanidine 2-Methyl-2-butanethiol 2-Methylbutanoic acid 3-Methylbutanoic acid (20⬚C) (E)-2-Methyl-2-butendioic acid (mesaconic acid) 3-Methyl-2-butenoic acid (E)-2-Methyl-2-butenoic acid (tiglic acid) (Z)-2-Methyl-2-butenoic acid (angelic acid) 4-Methylcarboxylphenol (E)-2-Methylcinnamic acid (E)-3-Methylcinnamic acid (E)-4-Methylcinnamic acid 1-Methylcyclohexane-1-carboxylic acid cis-2-Methylcyclohexane-1-carboxylic acid trans-2-Methylcyclohexane-1-carboxylic acid cis-3-Methylcyclohexane-1-carboxylic acid trans-3-Methylcyclohexane-1-carboxylic acid cis-4-Methylcyclohexane-1-carboxylic acid trans-4-Methylcyclohexane-1-carboxylic acid 2-Methylcyclohexyl-1,1-diacetic acid

9.83(⫹1)

pK2

pK3

1.1(⫹1)

4.72(⫹1)

7.30(⫺1)

—

—

7.85(⫺1)

pK4

8.70(⫹1) 9.65(⫹1) 10.06(⫹1) 4.85(⫹1) 3.41 4.35(⫹1) 3.386(⫹1) 1.44(⫹1) 3.66(⫹1) 4.68(⫹1) 6.29(⫹1) 3.90 4.269 4.362 8.65 3.00(⫹2) 11.35 4.761 4.767 3.09

8.18

11.44(⫹1)

4.75

5.12 4.96 4.30 8.47 4.500 4.442 4.564 5.13 5.03 5.73 4.88 5.02 5.04 4.89 3.53

6.89

short standard long

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(McGHP)

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.59

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 3-Methylcyclohexyl-1,1-diacetic acid 4-Methylcyclohexyl-1,1,1-diacetic acid 3-Methylcyclopentyl-1,1-diacetic acid S-Methyl-L-cysteine N-Methylcytidine 5-Methylcytidine N-Methyl-2⬘-deoxycytidine 5-Methyl-2⬘-deoxycytidine 2-Methyl-3,5-dinitrobenzoic acid 5-Methyldipropylenetriamine (30⬚C) 2,2⬘-Methylenebis(4-chlorophenol) 2,2⬘-Methylenebis(4,6-dichlorophenol) Methylenebis(thioacetic acid (18⬚C) 3,3⬘-(Methylenedithio)dialanine Methylenesuccinic acid N-Methylethylamine N-Methylethylenediamine ␣-Methylglucoside 3-Methylglutaric acid N-Methylglycine (sarcosine) 5-Methyl-2,4-heptanedione 5-Methyl-2,4-hexanedione 5-Methyl-4-hexenoic acid 3-Methylhistamine 1-Methylhistidine 2-Methylhistidine (18⬚C) 2-Methyl-8-hydroxyquinoline (␮ ⫽ 0.005) 4-Methyl-8-hydroxyquinoline 1-Methylimidazole 4-Methylimidazole N-Methyliminodiacetic acid S-Methylisothiourea O-Methylisourea Methylmalonic acid 2-(N-Methylmethanesulfonamido)pyridine 3-(N-Methylmethanesulfonamido)pyridine 4-(N-Methylmethanesulfonamido)pyridine 2-Methyl-6-methylaminopyridine (20⬚C) 3-Methyl-4-methylaminopyridine (20⬚C)

pK1

pK2

3.49

6.08

3.49

6.10

3.79

6.74

8.97 3.88 4.21 3.97 4.33 2.97 6.32(⫹3)

9.19(⫹2)

7.6 5.6 3.310 2.200(⫹1) 3.85 4.23(⫹1) 6.86(⫹1) 13.71 4.24 2.12(⫹1) 8.52(enol); 9.10(keto) 8.66(enol); 9.31(keto) 4.80 5.80(⫹1) 1.69 1.7 4.58(⫹1) 4.67(⫹1) 7.06(⫹1) 7.55(⫹1) 2.15 9.83(⫹1) 9.72(⫹1) 3.07 1.73(⫹1)

top of rh base of rh

pK3

pK4

10.33(⫹1)

11.5 10.56 4.345 8.16(0) 5.45 10.15(⫹1) 5.41 10.20(0)

9.90(0) 6.48 7.2 11.71(0)

8.85 9.5

11.62(0)

10.09

5.87

3.94(⫹1) 5.14(⫹1) 3.17(⫹1)

8.84(0)

—

9.84(0)

short standard long

DEAN #37261

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(McGHP)

8.60

INTERACTIVE

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SECTION 8

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

4-Methyl-2,2⬘-(4-methylpyridyl)pyridine N-Methylmorpholine 2-Methyl-1-naphthoic acid N-Methyl-1-naphthylamine 2-Methyl-4-nitrobenzoic acid 2-Methyl-6-nitrobenzoic acid 1-Methyl-2-nitroterephthalic acid 4-Methyl-2-nitroterephthalic acid 3-Methylpentanedioic acid 3-Methylpentane-2,4-dione 2-Methylpentanoic acid 3-Methylpentanoic acid 4-Methylpentanoic acid cis-3-Methyl-2-pentenoic acid trans-3-Methyl-2-pentenoic acid 4-Methyl-2-pentenoic acid 4-Methyl-3-pentenoic acid 6-Methyl-1,10-phenanthroline (2-Methylphenoxy)acetic acid (3-Methylphenoxy)acetic acid (4-Methylphenoxy)acetic acid (2-Methylphenyl)acetic acid (18⬚C) (4-Methylphenyl)acetic acid 5-Methyl-5-phenylbarbituric acid 3-(2-Methylphenyl)propanoic acid 3-(3-Methylphenyl)propanoic acid 3-(4-Methylphenyl)propanoic acid 1-Methyl-2-phenylpyrrolidine 5-Methyl-1-phenyl-1,2,3-triazole-4carboxylic acid Methylphosphinic acid Methylphosphonic acid 3-Methyl-o-phthalic acid 4-Methyl-o-phthalic acid N-Methylpiperazine (␮ ⫽ 0.1) 2-Methylpiperazine N-Methylpiperidine 2-Methylpiperidine 3-Methylpiperidine 4-Methylpiperidine (␮ ⫽ 0.5) 2-Methyl-1,2-propanediamine 2-Methyl-2-propanethiol 2-Methylpropanoic acid 2-Methyl-2-propylamine 2-Methyl-2-propylglutaric acid 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine Methyl 4-pyridinecarboxylate 6-Methylpyridine-2-carboxylic acid 2-Methylpyridine-1-oxide 3-Methylpyridine-1-oxide

5.32(⫹1) 7.13(⫹1) 3.11 3.70(⫹1) 1.86 1.87 3.11 1.82 4.25 10.87 4.782 4.766 4.845 5.15 5.13 4.70 4.60 5.11(⫹1) 3.227 3.203 3.215 4.35 4.370 8.011(0) 4.66 4.677 4.684 8.80 3.73 3.08 2.38 3.18 3.89 4.94(⫹2) 5.62(⫹2) 10.19(⫹1) 10.95(⫹1) 11.07(⫹1) 11.23(⫹1) 6.178(⫹2) 11.2 4.853 10.682(⫹1) 3.626 5.96(⫹1) 5.68(⫹1) 6.00(⫹1) 3.26(⫹1) 5.83 1.029(⫹1) 10.921(⫹1)

pK2

pK3

pK4

5.41

7.74

9.09(⫹1) 9.60(⫹1)

9.420(⫹1)

short standard long

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(McGHP)

RIGHT

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.61

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

4-Methylpyridine-1-oxide O-Methylpyridoxal (␮ ⫽ 0.16) Methyl-2-pyridyl ketoxime 1-Methyl-2-(3-pyridyl)pyrrolidine 1-Methylpyrrolidine 1-Methyl-3-pyrroline 5-Methylquinoline Methylsuccinic acid Methylsulfonylacetic acid 3-Methylsulfonylaniline 4-Methylsulfonylaniline 3-Methylsulfonylbenzoic acid 4-Methylsulfonylbenzoic acid 4-Methylsulfonyl-3,5-dimethylphenol 3-Methylsulfonylphenol 4-Methylsulfonylphenol 1-Methyl-1,2,3,4-tetrahydro-3-pyridinecarboxylic acid (arecaidine; isoguvacine) 5-Methyl-1,2,3,4-tetrazole 2-Methylthiazole (␮ ⫽ 0.1) 4-Methylthiazole (␮ ⫽ 0.1) 5-Methylthiazole (␮ ⫽ 0.1) Methylthioacetic acid 4-Methylthioaniline 2-Methylthioethylamine (30⬚C) Methylthioglycolic acid 3-(S-Methylthio)phenol 4-(S-Methylthio)phenol 2-Methylthiopyridine (20⬚C) 3-Methylthiopyridine (20⬚C) 4-Methylthiopyridine (20⬚C) 5-Methylthio-1,2,3,4-tetrazole O-Methylthreonine O-Methyltyrosine 1-Methylxanthine 3-Methylxanthine 7-Methylxanthine 9-Methylxanthine Morphine (20⬚C) Morpholine 2-(N-Morpholino)ethanesulfonic acid (MES) (20⬚C) 3-(N-Morpholino)-2-hydroxypropanesulfonic acid (37⬚C) 3-(N-Morpholino)propanesulfonic acid (20⬚C) Murexide Myosmine

1.258(⫹1) 4.74 9.97 3.41 10.46(⫹1) 9.88(⫹1) 4.62(⫹1) 4.13 2.36 2.68(⫹1) 1.48(⫹1) 3.52 3.64 8.13

1-Naphthalenecarboxylic acid (1-naphthoic acid)

pK2

top of rh base of rh

pK3

pK4

7.94

5.64

9.33 7.83 9.07

3.32 3.40(⫹1) 3.16(⫹1) 3.03(⫹1) 3.72 4.40(⫹1) 9.18(⫹1) 7.68 9.53 9.53 3.59(⫹1) 4.42(⫹1) 5.94(⫹1) 4.00(⫹1) 2.02(⫹1) 2.21(⫹1) 7.70 8.10 8.33 6.25 7.87(⫹1) 8.492(⫹1) 6.15

9.00(0) 9.35(0) 12.0 11.3 ca 13 9.85(0)

6.75 7.20 0.0 5.26 3.695

9.20

10.50

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 2-Naphthalenecarboxylic acid 1-Naphthol (20⬚C) 2-Naphthol (20⬚C) Naphthoquinone monoxime 1-Naphthylacetic acid 2-Naphthylacetic acid 1-Naphthylamine 2-Naphthylamine 1-Naphthylarsonic acid 1-Naphthysulfonic acid Narceine (15⬚C) Narcotine Nicotine Nicotyrine Nitrilotriacetic acid (NTA) (20⬚C) Nitroacetic acid 2-Nitroaniline 3-Nitroaniline 4-Nitroaniline 2-Nitrobenzene-1,4-dicarboxylic acid 3-Nitrobenzene-1,2-dicarboxylic acid 4-Nitrobenzene-1,2-dicarboxylic acid 2-Nitrobenzoic acid 3-Nitrobenzoic acid 4-Nitrobenzoic acid trans-2-Nitrocinnamic acid trans-3-Nitrocinnamic acid trans-4-Nitrocinnamic acid Nitroethane 2-Nitrohydroquinone N-Nitroiminodiacetic acid 3-Nitromesitol Nitromethane 1-Nitro-6,7-phenanthroline (␮ ⫽ 0.2) 5-Nitro-1,10-phenanthroline 6-Nitro-1,10-phenanthroline 2-Nitrophenol 3-Nitrophenol 4-Nitrophenol (2-Nitrophenoxy)acetic acid (3-Nitrophenoxy)acetic acid (4-Nitrophenoxy)acetic acid 2-Nitrophenylacetic acid 3-Nitrophenylacetic acid 4-Nitrophenylacetic acid 2-Nitrophenylarsonic acid 3-Nitrophenylarsonic acid 4-Nitrophenylarsonic acid 7-(4-Nitrophenylazo)-8-hydroxy-5quinolinesulfonic acid

pK1 4.161 9.30 9.57 8.01 4.236 4.256 3.92(⫹1) 4.11(⫹1) 3.66 0.57 3.5(⫹1) 6.18(⫹1) 3.15(⫹1) 4.76(⫹1) 1.65 1.68 ⫺0.28(⫹1) 2.46(⫹1) 1.01(⫹1) 1.73

pK2

pK3

pK4

8.66 9.3 7.87(0) 2.94

10.33

1.88 2.11 2.18 3.46 3.441 4.15 4.12 4.05 8.57 7.63 2.21 8.984 10.12 3.23(⫹1) 3.232(⫹1) 3.23(⫹1) 7.222 8.360 7.150 2.896 2.951 2.893 4.00 3.97 3.85 3.37 3.41 2.90 3.14(0)

10.06 3.33

8.54 7.80 7.80 7.495(⫺1)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 3-Nitrophenylphosphonic acid 4-Nitrophenylphosphonic acid 3-(2⬘-Nitrophenyl)propanoic acid 3-(4⬘-Nitrophenyl)propanoic acid 3-Nitrophenylselenic acid 4-Nitrophenylselenic acid 1-Nitropropane 2-Nitropropane 2-Nitropropanoic acid 2-Nitropyridine (␮ ⫽ 0.02) 3-Nitropyridine (␮ ⫽ 0.02) 4-Nitropyridine (␮ ⫽ 0.02) N-Nitrosoiminodiacetic acid 4-Nitrosophenol Nitrourea 1,9-Nonanedioic acid (azelaic acid) Nonanoic acid (pelargonic acid) DL-Norleucine Novocaine 2,2,3,3,4,4,5,5-Octafluoropentanoic acid 1,8-Octanedioic acid (suberic acid) Octanoic acid (caprylic acid) Octopine-DD Octopine-LD Octylamine L-(⫹)-Ornithine Oxalic acid 3,6-Oxaoctanedioic acid (␮ ⫽ 1.0) Oxoacetic acid 2-Oxabutanedioic acid (oxaloacetic acid) 2-Oxobutanoic acid 5-Oxohexanoic acid (5-ketohexanoic acid) (18⬚C) 3-Oxo-1,5-pentanedioic acid 4-Oxopentanoic acid (levulinic acid) 2-Oxopropanoic acid (pyruvic acid) Oxytetracycline Papaverine Pentamethylenebis(thioacetic acid) (18⬚C) 3,3-Pentamethylenepentanedioic acid 1,5-Pentanediamine 2,4-Pentanedione 1-Pentanoic acid (valeric acid) 2-Pentenoic acid 3-Pentenoic acid

pK1 1.30 1.24 4.504 4.473 4.07 4.00 8.98 7.675 3.79 ⫺2.06(⫹1) 0.79(⫹1) 1.23(⫹1) 2.28 6.48 4.15(⫹1) 4.53 4.95 2.335(⫹1) 8.85(⫹1)

top of rh base of rh

pK2

pK3

pK4

6.27 6.23

3.38

5.40 9.834(0)

2.65 4.512 4.895 1.35 1.40 10.65(⫹1) 1.94(⫹2) 1.271 3.055 3.46 2.56

5.404 2.30 2.30 8.65(⫹1) 4.272 3.676

8.68 8.72

11.25 11.34

10.76(0)

4.37

2.50 4.662 3.10 4.59 2.49 3.10(⫹1)

7.26

5.90(⫹1) 3.485

4.413

3.49

6.96

10.05(⫹2) 8.24(enol); 8.95(keto) 4.842 4.70 4.52

9.11

10.916(⫹1)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

4-Pentenoic acid Pentylarsonic acid N-Pentylveratramine Perhydrodiphenic acid (20⬚C) Perlolidine (18⬚C) Peroxyacetic acid 1,7-Phenanthroline 1,10-Phenanthroline 6,7-Phenanthroline Phenazine Phenethylthioacetic acid Phenol Phenol-3-phosphoric acid Phenol-4-phosphoric acid Phenolphthalein 3-Phenolsulfonic acid Phenosulsulfonephthalein Phenoxyactic acid 2-Phenoxybenzoic acid 3-Phenoxybenzoic acid 4-Phenoxybenzoic acid 5-Phenoxy-1,2,3,4-tetrazole Phenylacetic acid L-3-Phenyl-␣-alanine 3-Phenyl-␣-alanine, methyl ester Phenylalanylarginine (␮ ⫽ 0.01) Phenylalanylglycine (␮ ⫽ 0.01) 7-Phenylazo-8-hydroxy-5-quinolinesulfonic acid 5-Phenylbarbituric acid 2-Phenyl-2-benzylsuccinic acid 1-Phenylbiguanide 4-Phenylbutanoic acid Phenylbutazone 2-Phenylenediamine 3-Phenylenediamine 4-Phenylenediamine 2-Phenylethylamine ␤-Phenylethylboronic acid DL-␣-Phenylglycine Phenylguanidine Phenylhydrazine 2-Phenyl-3-hydroxypropanoic acid 3-Phenyl-3-hydroxypropanoic acid Phenyliminodiacetic acid (20⬚C) Phenylmalonic acid Phenylmethanethiol 2-Phenyl-2-phenethylsuccinic acid (20⬚C) 2-Phenylphenol 3-Phenylphenol 4-Phenylphenol Phenylphosphinic acid (17⬚C)

4.677 4.14 7.28(⫹1) 4.96 4.01 8.20 4.30(⫹1) 4.857(⫹1) 4.857(⫹1) 1.2(⫹1) 3.795 9.99 1.78 1.99 9.4 — 7.9 3.171 3.53 3.95 4.52 3.49(⫹1) 4.312 1.83(⫹1) 7.05(⫹1) 2.66(⫹1) 3.10(⫹1) 3.41(0) 2.544(⫹1) 3.69 2.13(⫹2) 4.757 4.5(⫹1) ⬍2(⫹2) 2.65(⫹2) 3.29(⫹2) 9.83(⫹1) 10.0 1.83(⫹1) 10.77(⫹1) 5.20(⫹1) 3.53 4.40 2.40 2.58 10.70 3.74 9.55 9.63 9.55 2.1

pK2

pK3

pK4

9.07 6.68 11.39

7.03 7.25

10.2 9.9

9.05(⫺1)

9.12(0) 7.57(0) 7.71(0) 7.850(⫺1)

12.40(⫺1)

6.47 10.76(⫹1)

4.47(⫹1) 4.88(⫹1) 6.08(⫹1)

4.39(0)

4.98 5.03 6.52

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

Phenylphosphonic acid O-Phenylphosphorylserine O-Phenylphosphorylserylglycine O-Phenylphosphoryl-L-seryl-L-leucine N-Phenylpiperazine (␮ ⫽ 0.1) 2-Phenylpropanoic acid 3-Phenylpropanoic acid (35⬚C) 3-Phenyl-1-propylamine Phenylpropynoic acid (35⬚C) Phenylselenic acid Phenylselenoacetic acid (␮ ⫽ 0.1) ␤-Phenylserine (␮ ⫽ 0.16) Phenylsuccinic acid (20⬚C) Phenylsulfenylacetic acid Phenylsulfonylacetic acid 5-Phenyl-1,2,3,4-tetrazole 1-Phenyl-1,2,3-triazole-4-carboxylic acid 1-Phenyl-1,2,3-triazole-4,5-dicarboxylic acid Phosphoramidic acid O-Phosphorylethanolamine O-Phosphorylserylglycine O-Phosphoryl-L-seryl-L-leucine Phosphoserine Phthalamide Phthalazine o-Phthalic acid Phthalimide Physostigmine Picric acid (2,4,6-trinitrophenol) (18⬚C) Pilocarpine Piperazine 1,4-Piperazinebis(ethanesulfonic acid) (20⬚C) Piperazine-2-carboxylic acid Piperdine 2-Piperidinecarboxylic acid 3-Piperidinecarboxylic acid 4-Piperidinecarboxylic acid 1-(2-Piperidinyl)-2-propanone (15⬚C) Piperine (15⬚C) Proline 1,2-Propanediamine 1,3-Propanediamine 1-Propanethiol 1,2,3-Propanetriamine 1,2,3-Propanetricarboxylic acid Propanoic acid Propenoic acid

1.83 2.13(⫹1) 3.18(⫹1) 3.16(⫹1) 8.71(⫹1) 4.38 4.664 10.39(⫹1) 2.269 4.79 3.75 8.79(0) 3.78 2.66 2.44 4.38(⫹1) 2.88 2.13 3.08 5.838(⫹1) 3.13 3.11 2.08 3.79(0) 3.47(⫹1) 2.950 9.90(0) 1.76(⫹1) 0.419 1.3(⫹1) 5.333(⫹2) 6.80 1.5 11.123(⫹1) 2.12(⫹1) 3.35(⫹1) 3.73(⫹1) 9.45 1.98(⫹1) 1.99(⫹1) 6.607(⫹2) 8.49(⫹2) 10.86 3.72(⫹3) 3.67 4.874 4.247

top of rh base of rh

pK2

pK3

pK4

7.07 8.79 6.95(0) 7.12(0)

5.55

4.93 8.63 10.638(0) 5.41 5.47 5.65

8.01 8.26 9.74

5.408 7.88(0)

6.85(0) 9.781(⫹1)

5.41

9.53

10.75(0) 10.64(0) 10.72(0)

10.96(0) 9.702(⫹1) 10.47(⫹1) 7.95(⫹2) 4.87

9.59(⫹1) 6.38

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance N-Propionyglycine 2-Propoxybenzoic acid (20⬚C) 3-Propoxybenzoic acid (20⬚C) 4-Propoxybenzoic acid (20⬚C) N-Propylalanine Propylamine Propylarsonic acid (18⬚C) Propylenimine N-Propylglycine (␮ ⫽ 0.1) L-Propylglycine Propylmalonic acid Propylphosphinic acid Propylphosphonic acid 2-Propylpyridine N-Propylveratramine 2-Propynoic acid Pseudoecgonine Pseudoisocyanine (␮ ⫽ 0.2) Pseudotropine Pteroylglutamic acid Purine Pyrazine Pyrazinecarboxamide Pyrazole Pyridazine Pyridine Pyridine-d5 2-Pyridinealdoxime 3-Pyridinealdoxime 4-Pyridinealdoxime 2-Pyridinecarbaldehyde 3-Pyridinecarbaldehyde 4-Pyridinecarbaldehyde 3-Pyridinecarbamide (nicotinamide) 3-Pyridinecarbonitrile Pyridine-2-carboxylic acid (picolinic acid) Pyridine-3-carboxylic acid (nicotinic acid) Pyridine-4-carboxylic acid (isonicotinic acid) Pyridine-2,3-dicarboxylic acid Pyridine-2,4-dicarboxylic acid Pyridine-2,6-dicarboxylic acid Pyridine-1-oxide Pyridoxal Pyridoxal-5-phosphate (␮ ⫽ 0.15) Pyridoxamine (␮ ⫽ 0.1) Pyridoxamine-5-phosphate (␮ ⫽ 0.15; pK 5 10.92)

pK1 3.718(0) 4.24 4.20 4.78 2.21(⫹1) 10.568(⫹1) 4.21 8.18(⫹1) 2.38(⫹1) 3.19(⫹1) 2.97 3.46 2.49 6.30(⫹1) 7.20(⫹1) 1.887 9.70 4.59(⫹2) 9.86(⫹1) 8.26 2.52(⫹1) 0.6(⫹1) 0.5(⫹1) 2.61(⫹1) 2.33(⫹1) 5.17(⫹1) 5.83(⫹1) 3.56(⫹1) 4.07(⫹1) 4.73(⫹1) 3.84(⫹1) 3.80(⫹1) 4.74(⫹1) 3.33(⫹1)

pK2

9.09 10.03(0) 8.97(0) 5.84 8.18

8.92(0)

10.17(0) 10.39(0) 10.03(0)

5.29(0)

2.07(⫹1)

4.75(0)

1.84(⫹1)

4.86(0)

2.36(⫹1) 2.23(⫹1) 2.16(⫹1) 0.688(⫹1) 4.20(⫹1)

7.08(0) 7.02(0) 6.92(0)

2.5

pK4

10.19(0)

1.35(⫹1) 1.01(⫹1)

⬍2.5 3.37(⫹2)

pK3

8.66(ring OH) 4.14 8.01(⫹1) 3.69

6.20 10.13(ring OH) 5.76

8.69

8.61

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

Pyridoxine (vitamin B6 ) (18⬚C)

5.00(⫹1)

3-(2⬘-Pyridyl)alanine 3-(3⬘-Pyridyl)alanine 2-(2⬘-Pyridyl)benzimidazole (␮ ⫽ 0.16) 2-(2⬘-Pyridyl)imidazole (␮ ⫽ 0.005) 4-(2⬘-Pyridyl)imidazole (␮ ⫽ 0.1) Pyrimidine 2,4(1H,3H)-Pyrimidinedione (uracil) 2,4,5,6(1H,3H)-Pyrimidinetetrone5-oxime Pyrocatecholsulfonephthaleine Pyroxilidine Pyrrole-1-carboxylic acid Pyrrole-2-carboxylic acid Pyrrole-3-carboxylic acid Pyrrolidine Pyrrolidine-2-carboxylic acid (proline) 2-[2-(N-Pyrrolidinyl)ethyl]pyridine 3-[2-(N-Pyrrolidinyl)ethyl]pyridine 4-[2-(N-Pyrrolidinyl)ethyl]pyridine 2-(1-Pyrrolidinylmethyl)pyridine 3-(1-Pyrrolidinylmethyl)pyridine 4-(1-Pyrrolidinylmethyl)pyridine 3-Pyrroline

1.37(⫹2) 1.77(⫹2) 5.58(⫹1)

5.49(⫹1) 1.30(⫹1) 0.6(⫹1)

7.82 11.11(⫹1) 4.45 4.45 4.453 11.305(⫹1) 1.952(⫹1) 3.60(⫹2) 4.28(⫹2) 4.65(⫹2) 2.54(⫹1) 3.14(⫹2) 3.38(⫹2) ⫺0.27(⫹1)

D-Raffinose

12.74 ca ⫺0.2 12.11 —

acid Saccharin (o-benzoic sulfimide) Sarcosine Sarcosine amide Sarcosine dimethylamide Sarcosine methylamide Sarcosylglycine (␮ ⫽ 0.16) Sarcosylleucine Sarcosylsarcosine Sarcosylserine 3-Selenosemicarbazide (␮ ⫽ 0.1) Semicarbazide (␮ ⫽ 0.1) L-Serine

pK4

9.22(0) 9.10(0)

9.46(0)

4.57(0)

4.0(⫹1) 4.11(⫹1) 4.80(⫹1) 0.72(⫹1)

D-Saccharic

pK3

8.98(⫹1)

Quinidine Quinine Quinoline Quinoxaline Riboflavin (vitamin B2) (␮ ⫽ 0.01) ␣-D-Ribofuranose D-Ribose-5⬘-phosphonic acid

pK2 8.96(ring OH) 4.02(⫹1) 4.64(⫹1)

top of rh base of rh

5.00(0) 2.32 2.12(⫹1) 8.35(⫹1) 8.86(⫹1) 8.28(⫹1) 3.15(⫹1) 3.15(⫹1) 2.92(⫹1) 3.17(⫹1) 0.8(⫹1) 3.53(⫹1) 2.21(⫹1)

9.76

11.73

10.640(0) 9.39(⫹1) 9.28(⫹1) 9.27(⫹1) 8.56(⫹1) 8.36(⫹1) 8.16(⫹1)

8.54(0) 8.52(0)

9.69 6.70(⫺1)

13.05(⫺2)

10.20(0)

8.56(0) 8.67(0) 9.15(0) 8.63(0)

9.15(0)

13.6

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance Serine, methyl ester (␮ ⫽ 0.1) Serylglycine (␮ ⫽ 0.15) L-Seryl-L-leucine Solanine D-Sorbitol (17.5⬚C) L-(⫺)-Sorbose (18⬚C) Sparteine Spinaceamine (␮ ⫽ 0.1) Spinacine L-Strychnine (15⬚C) Succinamic acid (succinic acid monoamide) Succinic acid DL-Succinimide ␤-(4⬘-Sulfaminophenyl)alanine 3-Sulfamylbenzoic acid 4-Sulfamylbenzoic acid 4-Sulfamylphenylphosphoric acid Sulfanilamide Sulfoacetic acid 3-Sulfobenzoic acid 4-Sulfobenzoic acid 3-Sulfophenol 4-Sulfophenol 2-Sulfopropanoic acid 5-Sulfosalicyclic acid Sylvic acid D-Tartaric

acid meso-Tartaric acid Tetracycline (␮ ⫽ 0.005) Tetradehydroyohimbine Tetraethylenepentamine [␮ ⫽ 0.1; pK 5 9.67(⫹1)] 1,4,5,6-Tetrahydro-1,2-dimethylpyridine 1,4,5,6-Tetrahydro-2-methylpyridine cis-Tetrahydronaphthalene-2,3-dicarboxylic acid (20⬚C) trans-Tetrahydronaphthalene-2,3dicarboxylic acid (20⬚C) 5,6,7,8-Tetrahydro-1-naphthol 5,6,7,8-Tetrahydro-2-naphthol Tetrahydroserpentine 2,3,5,6-Tetramethylbenzoic acid Tetramethylenebis(thioacetic acid) (18⬚C) Tetramethylenediamine N,N,N⬘,N⬘-Tetramethylethylenediamine 2,3,5,6-Tetramethyl-4-methylaminopyridine

pK1 7.03(⫹1) 2.10(⫹1) 3.08(⫹1) 7.34(⫹1) 13.60 11.55 4.49(⫹1) 4.895(⫹2) 1.649(⫹2) 2.50 4.39(0) 4.207 9.623 1.99(⫹1) 3.54 3.47 1.42 10.43(⫹1) — — — 0.39 0.58 1.99 2.49 7.62 3.036 3.22 3.30(⫹1) 10.59(⫹1) 2.98(⫹5)

pK2

pK3

pK4

7.33(0) 7.45(0)

11.76(0) 8.90(⫹1) 4.936(⫹1) 8.20

8.663(0)

5.635 8.64(0)

10.26(⫺1)

6.38

10.0

4.0 3.78 3.72 9.07 8.70 12.00

4.366 4.81 7.68

9.69

4.72(⫹4)

8.08(⫹3)

9.10(⫹2)

11.38(⫹1) 9.53(⫹1) 3.98

6.47

4.00

5.70

10.28 10.48 10.55(⫹1) 3.415 3.463 9.22(⫹2) 2.20(⫹2) 0.07(⫹1)

4.423 10.75(⫹1) 6.35(⫹1)

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TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

2,2,6,6-Tetramethylpiperidine (␮ ⫽ 0.5) 2,3,5,6-Tetramethylpyridine (20⬚C) Tetramethylsuccinic acid 1,2,3,4-Tetrazole Thebaine 2-Thenoyltriflluoroacetone Theobromine Theophylline Thiazoline Thioacetic acid o-Thiocresol m-Thiocresol p-Thiocresol Thiocyanatoacetic acid 2,2⬘-Thiodiacetic acid 4,4⬘-Thiodibutanoic acid (18⬚C) 3,3⬘-Thiodipropanoic acid (18⬚C) 3-Thio-S-methylcarbazide (␮ ⫽ 0.1) 1-Thionylcarboxylic acid 2-Thionylcarboxylic acid 2-Thiophenecarboxylic acid (30⬚C) 3-Thiophenecarboxylic acid (3thenoic acid) Thiophenol 3-Thiosemicarbazide (␮ ⫽ 0.1) 3-Thiosemicarbazide-1,1-diacetic acid (30⬚C) Thiourea Thorin Thymidine p-Toluenesulfinic acid Toluhydroquinone o-Toluidine m-Toluidine p-Toluidine o-Tolylacetic acid (18⬚C) p-Tolylacetic acid (18⬚C) o-Tolylarsonic acid m-Tolylarsonic acid p-Tolylarsonic acid o-Tolylphosphonic acid m-Tolylphosphonic acid p-Tolylphosphonic acid 3-Tolylselenic acid 4-Tolylselenic acid Triacetylmethane Triallylamine 1,3,5-Triazine-2,4,6-triol 1H-1,2,3-Triazole 1H-1,2,4-Triazole 1,2,3-Triazole-4-carboxylic acid

1.24(⫹1) 7.90(⫹1) 3.50 4.90 7.95(⫹1) 5.70(0) 0.68(⫹1) ⬍1(⫹1) 2.53(⫹1) 3.33 6.64 6.58 6.52 2.58 3.32 4.351 4.085 7.563(⫹1)

pK2

top of rh base of rh

pK3

pK4

7.28

7.89 8.80

4.29 5.275 5.075

3.53 4.10 3.529 4.10 6.50 1.5(⫹1) 2.94 2.03(⫹1) 3.7 9.79 1.7 10.03 4.45(⫹1) 4.71(⫹1) 5.08(⫹1) 4.36 4.36 3.82 3.82 3.70 2.10 1.88 1.84 4.80 4.88 5.81 8.31(⫹1) 7.20 — 2.386(⫹1) 3.22

4.07

8.3 12.85

11.8

11.62

8.85 8.60 8.68 7.68 7.44 7.33

11.10 9.26 9.972 8.73

short standard long

DEAN #37261

LEFT

(McGHP)

8.70

INTERACTIVE

top of rh base of rh

SECTION 8

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance 1,2,3-Triazole-4,5-dicarboxylic acid 1,2,4-Triazolidine-3,5-dione (urazole) Tribomoacetic acid 2,4,6-Tribromobenzoic acid Trichloroacetic acid Trichloroacrylic acid 3,3,3-Trichlorolactic acid Trichloromethylphosphonic acid 2,4,5-Trichlorophenol 3,4,5-Trichlorophenol Tricine (20⬚C) Triethanolamine Triethylamine Triethylenediamine Triethylenetetramine (20⬚C) Triethylsuccinic acid Trifluoroacetic acid Trifluoroacrylic acid 4,4,4-Trifluoro-2-aminobutanoic acid 4,4,4-Trifluoro-3-aminobutanoic acid 4,4,4-Trifluorobutanoic acid ␣,␣,␣-Trifluoro-m-cresol 4,4,4-Trifluorocrotonic acid 5,5,5-Trifluoroleucine 3-(Trifluoromethyl)aniline 4-(Trifluoromethyl)aniline 3-Trifluoromethylphenol 5-Trifluoromethyl-1,2,3,4-tetrazole 6,6,6-Trifluoronorleucine 5,5,5-Trifluoronorvaline 5,5,5-Trifluoropentanoic acid 3,3,3-Trifluoropropanoic acid 4,4,4-Trifluorothreonine 4,4,4-Trifluorovaline 1,2,3-Trihydroxybenzene (pyrogallol) 1,3,5-Trihydroxybenzene (phloroglucinol) 2,4,6-Trihydroxybenzoic acid 3,4,5-Trihydroxybenzoic acid 3,4,5-Trihydroxycyclohex-1-ene-1carboxylic acid [D-(⫺)-shikimic acid] 2,4,6-Tri(hydroxymethyl)phenol Triisobutylamine Trimethylamine 3-(Trimethylamino)phenol 4-(Trimethylamino)phenol

pK1 1.86

pK2 5.90

pK3

pK4

9.30

5.80 ⫺0.147 1.41 0.52 1.15 2.34 1.63 7.37 7.839 8.15 7.76(⫹1) 10.72(⫹1) 4.18(⫹2) 3.32(⫹4) 2.74 0.50 1.79 1.600(⫹1) 2.756(⫹1) 4.16 8.950 3.15 2.045(⫹1) 3.5(⫹1) 2.6(⫹1) 8.950 1.70 2.164(⫹1) 2.042(⫹1) 4.50 3.06 1.554(⫹1) 1.537(⫹1) 9.03(0)

4.81

8.19(⫹1) 6.67(⫹3)

9.92(⫹1)

8.169(0) 5.822(0)

8.942(0)

9.463(0) 8.916(0)

7.822(0) 8.098(0) 11.63(⫺1)

8.45(0)

8.88(⫺1)

1.68(0) 4.19(0) 4.15

8.85(⫺1)

9.56 10.42(⫹1) 9.80(⫹1) 8.06 8.35

9.20(⫹2)

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.71

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance

pK1

2,4,6-Trimethylaniline 2,4,6-Trimethylbenzoic acid Trimethylenebis(thioacetic acid) (18⬚C) 2,3,4-Trimethylphenol 2,4,5-Trimethylphenol 2,4,6-Trimethylphenol 3,4,5-Trimethylphenol 2,3,6-Trimethylpyridine (␮ ⫽ 0.5) 2,4,6-Trimethylpyridine 2,4,6-Trimethylpyridine-1-oxide 3-(Trimethylsilyl)benzoic acid 4-(Trimethylsilyl)benzoic acid 2,4,5-Trimethylthiazole (␮ ⫽ 0.1) 2,4,6-Trinitroaniline (picramide) 2,4,6-Trinitrobenzene acid 2,2,2-Trinitroethanol Trinitromethane (20⬚C) Triphenylacetic acid Tripropylamine Tris(2-hydroxyethyl)amine Tri(hydroxymethyl)aminomethane (TRIS) 2-[Tris(hydroxymethyl)methyl amino]-1-ethanesulfonic acid (TES) 3-[Tris(hydroxymethyl)methyl amino]-1-propanesulfonic acid (TAPS) (20⬚C) N-[Tris(hydroxymethyl)methyl]glycine (tricine) Tris(trimethylsilyl)amine Trithiocarbonic acid (20⬚C) Tropacocaine (15⬚C) 3-Tropanol (tropine) Trypsin (␮ ⫽ 0.1) L-Tryptophan DL-Tyrosine Tyrosine amide Tyrosine, ethyl ester Tyrosylarginine (␮ ⫽ 0.01) Tyrosyltyrosine

4.38(⫹1) 3.448 3.435

␣-Ureidobutanoic acid ␥-Ureidobutanoic acid ␤-Ureidopropanoic acid Uric acid Uridine Uridine-5⬘-diphosphoric acid Uridine-5⬘-phosphoric acid (5⬘-uridylic acid) Uridine-5⬘-triphosphoric acid

pK2

top of rh base of rh

pK3

pK4

5.383

10.59 10.57 10.88 10.25 7.60(⫹1) 7.43(⫹1) 1.990(⫹1) 4.089 4.192 4.55 ⫺10.23(⫹1) 0.654 2.36 0.17 3.96 10.66(⫹1) 7.762(⫹1) 8.08(⫹1) 7.50

8.4

2.023(⫹1) 4.70(⫹1) 2.64 9.88(⫹1) 10.33(⫹1) 6.25 2.38(⫹1) 2.18(⫹1) 7.48 7.33 2.65(⫹1) 3.52(⫹1) 3.886(0) 4.683(0) 4.487(0) 5.40 9.30 7.16 6.63 7.58

8.135

9.39(0) 9.11(0) 9.89 9.80 7.39(0) 7.68(0)

10.6(OH)

9.36(⫺1) 9.80(⫺1)

11.62(⫺2) 10.26(⫺2)

5.53

short standard long

DEAN #37261

LEFT

(McGHP)

8.72

INTERACTIVE

top of rh base of rh

SECTION 8

cap height base of text

TABLE 8.8 pKa Values of Organic Materials in Water at 25⬚C (Continued) Substance DL-Valine L-Valine

Valine amide (␮ ⫽ 0.2) L-Valine, methyl ester L-Valylglycine Vetramine Veratrine Vinylmethylamine 2-Vinylpyridine 4-Vinylpyridine Vitamin B12 Xanthine (40⬚C) Xanthosine Xylenol Orange [pK 5 10.46(⫺4); pK 6 12.28(⫺5)] D-(⫹)-Xylose Zincon

pK1 2.32(⫹1) 2.296(⫹1) 8.00 7.49(⫹1) 3.23(⫹1) 7.49(⫹1) 8.85(⫹1) 9.69(⫹1) 4.98(⫹1) 5.62(⫹1) 7.64(⫹1) 0.68(⫹1) ⬍2.5(⫹1) —

pK2

pK3

pK4

9.61(0) 9.79(0)

8.00(0)

5.67(0) 2.58(⫺1)

12.00(⫺1) 3.23(⫺2)

6.37(⫺3)

12.15(0) —

4

7.85

15

short standard long

DEAN #37261

TABLE 8.9 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures Abbreviations Used in the Table (⫺2), doubly ionized anion pKauto , negative logarithm (base 10) of autoprotolysis constant pKsp , negative logarithm (base 10) of solubility product

(McGHP)

(⫹1), protonated cation (0), neutral molecule (⫺1), singly ionized anion

Temperature, ⬚C

Acetic acid (0) DL-N-Acetylalanine (⫹1) ␤-Acetylaminopropionic (⫹1) N-Acetylglycine (⫹1) ␣-Alanine (⫹1) (0) 2-Aminobenzenesulfonic acid (0), pK 2 3-Aminobenzenesulfonic acid (0), pK 2 4-Aminobenzenesulfonic acid (0), pK 2 3-Aminobenzoic acid (0) 4-Aminobenzoic acid (0) 2-Aminobutyric acid (⫹1) (0) 4-Aminobutyric acid (⫹1) (0) 2-Aminoethylsulfonic acid (0)

4.780

5 4.770 3.699 4.479 3.682

2.42 10.59

10

15

4.762 3.699 4.465 3.676

4.758 3.703 4.465 3.673

2.39 10.29

20

25

30

4.757 3.708 4.449 3.667

4.756 3.715 4.445 3.670

4.757 3.725 4.444 3.673

2.34 9.87

2.35 10.01

35

40

50

4.762 3.733 4.443 3.678

4.769 3.745 4.445 3.685

4.787 3.774 4.457 3.706

2.33 9.74

2.33 9.62

2.33 9.49

2.33 9.26

2.633

2.591

2.556

2.521

2.448

2.459

2.431

2.404

2.380

2.338

4.075

4.002

3.932

3.865

3.799

3.738

3.679

3.622

3.567

3.464

3.521

3.457

3.398

3.338

3.283 4.90 4.95

3.227 4.79 4.85

3.176 4.75 4.90

3.126

3.079 4.68 4.95

2.989 4.60 5.10

2.334 10.530 4.057 11.026 9.452

2.28937.5⬚C 9.51837.5⬚C

2.286 9.380 4.046 10.867 9.316

4.038 10.706 9.186

4.031 10.556 9.061

4.027 10.409 8.940

4.025 10.269 8.824

INTERACTIVE

0

RIGHT

Substance

2.297 9.234 4.027 10.114 8.712

4.032 9.874 9.499

8.73

top of page

short standard

base of DF

DEAN #37261

TABLE 8.9 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures (Continued) Temperature, ⬚C 5

2.3651⬚C 10.4601⬚C 9.612

15

20

2.33812.5⬚C 10.10012.5⬚C 9.433

2.4191⬚C 10.9601⬚C

9.266

9.104

8.951

2.347 10.15412.5⬚C

3.656 11.000 9.873 10.081

3.627 10.830 9.704 9.904

1.914 9.718

1.885 9.563

9.549 9.731

3.583 10.526 9.398 9.564

1.870 9.407

4.220 9.380

1.786

30

8.801

35

2.31737.5⬚C 9.43937.5⬚C 8.659

8.519

2.357 10.205

2.35137.5⬚C 9.87237.5⬚C

2.318 9.808

9.49037.5⬚C

9.252 9.400

3.551 10.235 9.114 9.245

1.849 9.270

1.837 9.123

3.969 8.493 4.215 9.327 2.875 3.818 4.011 1.814

3.980 8.435 4.206 9.280 2.887 3.813 4.005 1.839

40

50

2.332 9.157 8.385

8.132 2.356 9.561

2.309

2.313 9.198

8.978 9.093

3.524 9.963 8.846 8.947

3.517 9.842 8.717 8.805

8.477 8.539

1.823 8.994

1.814 8.859

1.801 8.739

1.800 8.614

1.787 8.385

4.02 8.372 4.204 9.236 2.902 3.810 3.99 1.855

4.00 8.302 4.203 9.197 2.918 3.808 4.001 1.879

4.008 8.227 4.207 9.161 2.936 3.810 4.001 1.900

4.017 8.147 4.219 9.132

4.032 7.974 4.223 9.080

INTERACTIVE

4.231 9.439

25

2.320 9.758

2.38012.5⬚C 10.58012.5⬚C

2.3761⬚C 10.5081⬚C

9.508

10

LEFT

2-Amino-3-methylpentanoic acid (⫹1) (0) 2-Amino-2-methyl1,3-propanediol 2-Amino-2-methylpropionic acid (⫹1) (0) 2-Aminopentanoic acid (⫹1) (0) 3-Aminopropionic acid (⫹1) (0) 4-Aminopyridine (⫹1) Ammonium ion (⫹1) Arginine (⫹1) (0) Barbituric acid (⫹1) (0) Benzoic acid (0) Boric acid (0) Bromoacetic acid (0) 3-Bromobenzoic acid (0) 4-Bromobenzoic acid (0) Bromopropynoic acid (0)

0

(McGHP)

Substance

3.813 4.003 1.919

8.74

top of page

short standard

base of DF

4.231 4.425 2.611 4.810 3.890 3.879

4.199 4.389 2.620 4.817 3.892 3.876

4.170 4.354 2.618 4.827 3.896 3.874

4.143 4.320 2.621 4.840 3.902 3.873

4.119 4.287 2.631 4.854 3.908 3.875

4.885 3.931 3.888

6.382 10.377 2.856 3.831 3.991 1.820

6.352 10.329 2.867 3.83 3.986 1.845

6.327 10.290 2.883 3.825 3.981 1.864

6.309 10.250 2.900 3.826 3.980 1.879

6.296 10.220

6.285 10.172

1.766

6.429 10.431 2.845 3.838 4.000 1.796

3.200 4.813 6.386 2.445

3.176 4.797 6.383 2.447

3.160 4.782 6.384 2.452

3.142 4.769 6.388 2.460

3.128 4.761 6.396 2.460

3.116 4.755 6.406 2.482

3.109 4.751 6.423 2.496

3.099 4.750 6.439 2.511

2.342 8.30

2.360 8.22

2.379 8.169

2.400 8.094

2.422 8.020

2.446 7.948

2.471 7.877

2.498 7.808

2.129 7.400

2.136 7.401 3.663 4.154 3.911 3.234 4.292

2.144 7.408 3.687 4.187 3.954 3.304 4.299

2.151 7.417 3.771 4.217 3.990 3.362 4.302

2.160 7.428 3.726 4.244 4.020 3.409 4.304

2.172 7.441 3.762 4.268 4.045 3.445 4.306

2.187 7.457 3.788 4.290 4.065 3.472 4.306

4.806

4.804 3.898 3.911

2.618 4.803 3.894 3.900

6.577 10.627

6.517 10.558

6.465 10.499

3.220 4.837 6.393

8.40

10.34

6.047 10.068 10.14

2.60

5.926 9.882 9.94

2.73

7.673

INTERACTIVE

6.169 10.268

3.095 4.757 6.484

RIGHT

6.294 10.446

3.829 3.981 1.893

5.803 9.684 9.76

2.85

2.96

(McGHP)

4.266 4.463 2.626 4.805 3.891 3.889

DEAN #37261

3-tert-Butylbenzoic acid (0) 4-tert-Butylbenzoic acid (0) 2-Butynoic acid (0) Butyric acid (0) DL-N-Carbamoylalanine (⫹1) N-Carbamoylglycine (⫹1) Carbon dioxide ⫹ water (0) (⫺1) Chloroacetic acid (0) 3-Chlorobenzoic acid (0) 4-Chlorobenzoic acid (0) Chloropropynoic acid (0) Citric acid (0) (⫺1) (⫺2) Cyanoacetic acid (0) 2-Cyano-2-methylpropionic acid (0) 5,5-Diethylbarbituric acid (0) Diethylmalonic acid (0) (⫺1) 2,3-Dimethylbenzoic acid (0) 2,4-Dimethylbenzoic acid (0) 2,5-Dimethylbenzoic acid (0) 2,6-Dimethylbenzoic acid (0) 3,5-Dimethylbenzoic acid (0) N,N⬘-DimethylethyleneamineN,N⬘-diacetic acid (0) (⫺1) N,N-Dimethylglycine (0) 3,5-Dinitrobenzoic acid (0)

3.07

8.75

top of page

short standard

base of DF

DEAN #37261

TABLE 8.9 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures (Continued) Temperature, ⬚C

4.623

Hexanoic acid (0) Hydrogen cyanide (0) Hydrogen peroxide (0) Hydrogen sulfide (0) (⫺1) 4-Hydroxybenzoic acid (0) Hydroxylamine (0) 2-Hydroxy-1-naphthoic acid (0) (⫺1)

4.840

3.786

10

15

4.664

20

25

30

35

4.710 7.517 2.571 3.753

4.758 7.377 2.604 3.752 3.200 6.510 6.666

7.311 2.624 3.758 3.216 6.519 6.679

40

50

4.812 7.248

4.869 7.130

3.766 3.239 6.531 6.695

3.782 6.561 6.733

3.772

3.762

7.592 2.555 3.757

6.506 6.642

6.500 6.641

6.499 6.643

6.500 6.648

4.751 7.445 2.586 3.751 3.164 6.504 6.656

1.223 6.657

1.245 6.650

1.271 6.646

1.301 6.646

1.335 6.650

1.372 6.657

1.413 6.666

1.457 6.679

1.554 6.712

2.380 10.044

2.36 9.91

2.34 9.65

2.943

2.33 9.53 3.83337.5⬚C 2.944

2.327 9.412

2.952

2.351 9.780 3.831 2.942 3.126 8.252

2.32 9.19 3.849 2.959 3.159 7.668 4.920

10.34 3.875 2.968

2.397 10.193 3.84412.5⬚C 2.958

3.201 8.59412.5⬚C 4.839 9.63

12.23 7.33 13.5

7.24

9.49 11.86 7.13 13.2 4.596 6.186

4.849 9.36 11.75 7.05 4.586 6.063 3.29 9.68

9.21 11.65 6.97 12.90 4.582 5.948

2.942

2.947

7.94837.5⬚C 4.865 9.11 11.55 6.90 12.75 4.577

3.24 9.65

8.99 11.45 6.82 12.6 4.576 5.730

4.890 8.88

11.21 6.79

6.69

INTERACTIVE

2-Ethylbutyric acid (0) 5-Ethyl-5-phenylbarbituric acid (0) Fluoroacetic acid (0) Formic acid (0) 2-Furancarboxylic acid (0) Glucose-1-phosphate (0) Glycerol-1-phosphoric acid (⫺1) Glycerol-2-phosphoric acid (0) (⫺1) Glycine (⫹1) (0) Glycolic acid (0) Glycylasparagine (⫹1) N-Glycylglycine (⫹1)

5

LEFT

0

(McGHP)

Substance

4.578

3.19 9.61

3.26 9.58

8.76

top of page

short standard

base of DF

3.873

1.85012.5⬚C 9.95812.5⬚C 3.868

3.537 5.119

3.520 5.108

3.494 5.098

7.82 7.581

7.75 7.467

7.69 7.334

2.3831⬚C 10.4581⬚C 5.670

3.857

3.482 5.096 8.83 7.63 7.216 3.143

3.472 5.096 7.58 7.103 3.158

2.33812.5⬚C 10.10012.5⬚C

2.365 10.460

3.880 8.01

3.861

2.299 3.873

5.665

2.320 3.868

2.34812.5⬚C 10.0951.5⬚C 5.667 12.45 18.65

17.12

2.343 3.862 7.87

5.673 18.48 16.84

2.365 3.857

5.683 18.27

3.452 5.099 7.50 6.887 3.193

2.138 10.474

2.142 10.287

2.146 10.088 4.285 4.376 4.767 4.837

4.303 4.390

2.328 9.744 5.696 12.08 17.88 16.71 10.62

4.269 4.362

3.446 5.104 8.47 7.46 6.784 3.213

3.873 3.444 5.117 8.3745⬚C 6.685

2.31737.5⬚C 9.43937.5⬚C 2.427 3.861

5.710

16.65 10.466 2.150 9.920 4.256 4.349 4.794 4.853

2.452 3.867 7.73 2.32737.5⬚C 9.43437.5⬚C 5.730

1.796 9.138 3.895 3.445 5.149 7.05 6.497

2.332 9.157 2.481 3.873

5.753 11.81

3.895 7.63 2.333 9.142 5.803

16.79 16.53

4.244 4.336

10.161

9.876

2.154 9.763 4.235 4.322 4.831 4.879

4.871 4.908

8.77

INTERACTIVE

10.787

2.401 3.858 7.80

1.79837.5⬚C 9.39437.5⬚C 3.867

RIGHT

11.130

4.742 4.827

3.458 5.097 8.60 7.54 6.993 3.175

3.861

2.318 9.758

11.496

4.726 4.827

1.818 9.662 3.858

(McGHP)

1.9001⬚C 10.2741⬚C 3.880

DEAN #37261

4-Hydroxyproline (⫹1) (0) 2-Hydroxypropionic acid (0) DL-2-Hydroxysuccinic acid (0) (⫺1) Hypobromous acid (0) Hypochlorous acid (0) Imidazole (⫹1) Iodoacetic acid (0) DL-Isoleucine (⫹1) (0) Isopropylmalonic acid, mononitrile (0) Lactic acid (0) Lead sulfate, pKsp DL-Leucine (⫹1) (0) Malonic acid (⫺1) Mannose (0) Mercury(I) chloride, pKsp Methanol (solvent), pKauto Methylamine (⫹1) Methylaminodiacetic acid (0) (⫺1) 3-Methylbenzoic acid (0) 4-Methylbenzoic acid (0) 3-Methylbutyric acid (0) 4-Methylpentanoic acid (0)

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DEAN #37261

TABLE 8.9 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures (Continued) Temperature, ⬚C 5

10

15

8.104 4.825 11.439

4.827 11.240

11.048

20

8.057 4.840 10.862

⫺1.65 1.69 2.95 10.59

1.65 2.95 10.45 3.448 3.244

4.216

2.056 7.313 2.925 5.432 11.963 2.011 11.296

2.35612.5⬚C 10.19012.5⬚C 4.227

8.011 4.853 10.682 ⫺1.38

3.441 3.138

2.073 7.282

4.763 9.75 2.088 7.254

2.107 7.231

2.127 7.213

2.335 9.834 4.272 8.95 4.842 9.31 2.148 7.198

2.927 5.418 11.786

2.931 5.410 11.613

2.937 5.405 11.443

2.943 5.405 11.280

2.950 5.408 11.123

4.250

1.952 10.640 4.247

4.240

4.254 4.835

1.96412.5⬚C 10.97212.5⬚C 4.267

30

7.966 4.886 10.511

35

7.922

40

50

7.879 4.918

7.797 4.955

10.341 ⫺1.20

1.66 2.96 10.23 3.441

4.295

1.67 2.98 3.442 3.100 2.32437.5⬚C 9.51337.5⬚C 4.318

2.958 5.416 10.974

4.249

2.328 9.224 4.409

2.196 7.185

4.349 8.90 4.861 8.96 2.224 7.181

2.277 7.183

2.967 5.427 10.818

2.978 5.442 10.670

3.001 5.485 10.384

4.851 2.171 7.189

3.445

1.95037.5⬚C 10.34237.5⬚C 4.267

4.906

INTERACTIVE

2.394 10.564 4.210 9.07 4.823

1.65 2.94 10.33 3.444 3.177

25

LEFT

5-Methyl-5-phenylbarbituric acid (0) 2-Methylpropionic acid (0) 2-Methyl-2-propylamine (⫹1) Nitric acid (0) Nitrilotriacetic acid (0) (⫺1) (⫺2) 4-Nitrobenzoic acid (0) Nitrous acid (0) DL-Norleucine (⫹1) (0) Oxalic acid (⫺1) 2,4-Pentanedione (0) Pentanoic acid (0) Phenylalanine (0) Phosphoric acid (0) (⫺1) o-Phthalic acid (0) (⫺1) Piperidine (⫹1) Proline (⫹1) (0) Propenoic acid (0)

0

(McGHP)

Substance

1.958 10.064 4.301

8.78

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short standard

base of DF

3.728 12.17

11.98

2.2961⬚C 9.8801⬚C

3.723 1.791 11.81

4.263 5.660 1.8124.3⬚C

3.118 4.426

3.095 4.407

12.83 10.152 4.245 5.649

12.57

2.2001⬚C 9.7481⬚C

4.514

4.505

3.750 11.56

11.61 9.21

2.132 8.628 11.19 8.88

4.207 5.635 1.987 1.89

4.198 6.541 2.05

4.191 5.647 2.095 1.98

4.188 5.654 2.17

4.186 5.680 2.246 2.12

3.057 4.381 3.310

3.044 4.372 3.367

3.036 4.366 3.415

3.025 4.365 3.453

3.019 4.367 3.483

3.018 4.372 3.505

3.021 4.391

4.58

4.495

2.088 9.100 4.45

4.345

2.07037.5⬚C 8.81237.5⬚C 4.28

4.20

2.451 10.205

2.418 10.083 4.19 7.861 3.391 4.116 4.230 4.490

2.327 9.768 4.30 7.666 3.498 4.060 4.155 4.486

7.570 3.541 4.029 4.119 4.486

4.38 7.477 3.577 3.996 4.084 4.488

7.963 3.325 4.142 4.270 4.497

2.386 9.972 7.762 3.448 4.089 4.192 4.487 2.296 9.719

2.29237.5⬚C 9.40537.5⬚C

2.055 8.548

4.53 7.299

4.500

INTERACTIVE

2.29712.5⬚C 10.06412.5⬚C

2.15437.5⬚C 8.90437.5⬚C 11.83 9.381

3.731 1.963 10.84

RIGHT

8.067

12.07

3.725 1.932 10.99

4.218 5.639

2.13212.5⬚C 9.42012.5⬚C

8.173

2.186 9.208 12.30 9.749

3.721 1.940 11.15

4.232 5.642 1.894

1.74 3.075 4.391

3.718 1.887 11.30

(McGHP)

4.285 5.674 1.778 1.63

2.320 10.413

3.716 1.867 11.43

2.23212.5⬚C 9.54212.5⬚C 13.33 10.595

8.290

3.718 1.829 11.63

DEAN #37261

N-Propionylglycine (⫹1) Propynoic acid (0) Pyrrolidine (⫹1) Serine (⫹1) (0) Silver bromide, pKsp Silver chloride, pKsp Succinic acid (0) (⫺1) Sulfuric acid (⫺1) Sulfurous acid (0) D-Tartaric acid (0) (⫺1) 2,3,5,6-Tetramethylbenzoic acid (0) Threonine (⫹1) (0) o-Toluidine (0) 1,2,4-Triazole (⫹1) (0) 3,4,5-Trihydroxybenzoic acid (0) Tris(2-hydroxyethyl)amine (⫹1) 2,4,6-Trimethylbenzoic (0) 3-Trimethylsilylbenzoic acid (0) 4-Trimethylsilylbenzoic acid (0) ␤-Ureidopropionic acid (0) DL-Valine (⫹1) (0)

2.310 9.124

8.79

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DEAN #37261

LEFT

(McGHP)

8.80

INTERACTIVE

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SECTION 8

cap height base of text

FIGURE 8.1 Approximate potential ranges in nonaqueous solvents.

TABLE 8.10 Properties of Common Acid-Base Solvents

Solvent Acetic acid Acetic anhydride Acetone Acetonitrile Ammonia (at ⫺50⬚C) n-Butanol n-Butylamine Chlorobenzene N,N-Dimethylformamide Dimethylsulfoxide Ethanol Ethanolamine Ethyl acetate Ethylenediamine Formic acid Methanol 4-Methyl-2-pentanone (methyl isobutyl ketone) Nitromethane 2-Propanol Pyridine Sulfuric acid Water

Potential Span, mV 400 800 1600 1600 900 500 1500 1300 800 1500 500 200 800 1600 1000 900 1000 800

⫺log Ks 14.5 14.5 26.5 33

18.0 17.3 19.1 5.1 15.3 6.2 16.7 25.0

3.85 14.0

Dielectric Constant, 25⬚C 6.1(20⬚) 20.7(20⬚) 20.7 37.5(20⬚) 22(⫺33⬚) 17.1 4.88(20⬚) 5.62 36.71 46.6 24.55 37.7 6.02 14.2(20⬚) 58.5 32.7 13.1(20⬚) 35.8(30⬚) 19.92 12.3 101 78.3

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

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TABLE 8.11 pKa Values for Proton-Transfer Reactions in Nonaqueous Solvents Acid

Methanol

Ethanol

Acetic acid p-Aminobenzoic acid Ammonium ion Anilinium ion Benzoic acid Bromocresol purple Bromocresol green Bromophenol blue Bromothymol blue Di-n-butylammonium ion o-Chloroanilinium ion Cyanoacetic acid 2,5-Dichloroanilinium ion Dimethylaminoazobenzene N,N⬘-Dimethylanilinium ion Formic acid Hydrobromic acid Hydrochloric acid Methyl orange Methyl red (acid range) (alkaline range) Methyl yellow Neutral red o-Nitrobenzoic acid m-Nitrobenzoic acid p-Nitrobenzoic acid Perchloric acid Phenol Phenol red Phthalic acid, pK2 Picric acid Pyridinium ion Salicylic acid Stearic acid Succinic acid, pK2 Sulfuric acid, pK1 Tartaric acid, pK2 Thymol blue (alkaline range) (acid range) Thymolbenzein (acid range) (alkaline range) p-Toluenesulfonic acid p-Toluidinium ion Tribenzylammonium ion Tropeoline 00 Urea (protonated cation) Veronal

9.52 10.25 10.7 6.0

10.32

a

Dimethylsulfoxide.

b

11.3 9.8 8.9 12.4

top of rh base of rh

Other Solvents 11.4a, 9.75d 6.40b

5.70 10.72 11.5 10.65 9.5 13.2

10.0a

10.3a 3.4 7.49 9.48b 6.32b

5.2 4.37 9.15

5.5c 8.55b, 8.9c 3.8 4.1 9.2 3.4 8.2 7.6 8.3 8.4

3.4 3.55 10.45 3.55 8.2

4.87b 14.0 12.8 11.65 3.8 8.7 10.0 11.4

13.4 3.8

11.5d, 6.10d(pK1 ) 8.9c 6.1b

7.9

7.24b,c 9.9 14.0 4.7 3.5 13.1

15.2 5.35

8.44b 6.24 5.40b 2.2 6.96b 12.6

Glacial acetic acid. cAcetonitrile. dAcetone ⫹ 10% water.

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8.82

8.2.2

LEFT

(McGHP)

INTERACTIVE

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SECTION 8

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Formation Constants of Metal Complexes

Each value listed in Tables 8.12 and 8.13 is the logarithm of the overall formation constant for the cumulative binding of a ligand L to the central metal cation M, viz.:

Cumulative formation constant M ⫹ L ⫽ ML M ⫹ 2L ⫽ ML 2 ................. M ⫹ nL ⫽ MLn

Stepwise stability constants

K1 K2

k1 k1 k2

Kn

k1 k2 · · · kn

As an example, the entries in Table 8.12 for the zinc ammine complexes represent these equilibria: Zn2⫹ ⫹ NH3 ⫽ Zn(NH3 )2⫹

K1 ⫽

[Zn(NH3 )2⫹] [Zn2⫹][NH3 ]

Zn2⫹ ⫹ 2NH3 ⫽ Zn(NH3 )22⫹

K2 ⫽

[Zn(NH3 )22⫹] [Zn2⫹][NH3 ]2

Zn2⫹ ⫹ 3NH3 ⫽ Zn(NH3 )32⫹

K3 ⫽

[Zn(NH3 )32⫹] [Zn2⫹][NH3 ]3

Zn2⫹ ⫹ 4NH3 ⫽ Zn(NH3 )42⫹

K4 ⫽

[Zn(NH3 )42⫹] [Zn2⫹][NH3 ]4

If the stepwise stability or formation constants of the reactions are desired, for the first step log K1 ⫽ log k1 ⫽ 2.37. For the second and succeeding steps the equilibria and corresponding constants are as follows: Zn(NH3 )2⫹ ⫹ NH3 ⫽ Zn(NH3 )22⫹

log k2 ⫽ log K2 ⫺ log K1 ⫽ 2.44

Zn(NH3 )22⫹ ⫹ NH3 ⫽ Zn(NH3 )23⫹

log k3 ⫽ log K3 ⫺ log K2 ⫽ 3.50

Zn(NH3 )23⫹ ⫹ NH3 ⫽ Zn(NH3 )24⫹

log k4 ⫽ log K4 ⫺ log K3 ⫽ 2.15

The reverse of the association or formation reactions would represent the dissociation or instability constant for the systems, i.e., ⫺log Kf ⫽ log Kinstab . The data in the tables generally refer to temperatures of about 20 to 25⬚C. Most of the values in Table 8.12 refer to zero ionic strength, but those in Table 8.13 often refer to a finite ionic strength.

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

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TABLE 8.12 Cumulative Formation Constants for Metal Complexes with Inorganic Ligands

Ammonia Cadmium Cobalt(II) Cobalt(III) Copper(I) Copper(II) Iron(II) Manganese(II) Mercury(II) Nickel Platinum(II) Silver(I) Zinc Bromide Astatine Bismuth(III) Bromine Cadmium Cerium(III) Copper(I) Copper(II) Gold(I) Indium Iodine Iron(III) Lead Mercury(II) Palladium(II) Platinum(II) Rhodium(III) Scandium Silver(I) Thallium(I) Thallium(III) Tin(II) Uranium(IV) Yttrium Chloride Americium(III) Antimony(III) Bismuth(III) Cadmium Cerium(III) Copper(I) Copper(II) Curium(III) Gold(III) Indium Iron(II) Iron(III) Lead Manganese(II) Mercury(II)

log K1

log K2

log K3

log K4

log K5

log K6

2.65 2.11 6.7 5.93 4.31 1.4 0.8 8.8 2.80

4.75 3.74 14.0 10.86 7.98 2.2 1.3 17.5 5.04

6.19 4.79 20.1

7.12 5.55 25.7

6.80 5.73 30.8

5.14 5.11 35.2

11.02

13.32

12.86

18.5 6.77

19.28 7.96

8.71

3.24 2.37

7.05 4.81

7.31

9.46

5.89

7.82

3.32

3.70

2.51 [AtBr] 4.30 5.55 1.24 [Br ⫺3 ] 1.75 2.34 0.42 5.89 0.30 12.46 1.30 1.88 2.64 [IBr] ⫺0.30 ⫺0.50 1.2 1.9 9.05 17.32

2.08 4.38 0.93 9.7 1.11 0.18 1.32 1.17 2.26 2.44 1.95 0.48 0.1 1.17 1.42 0.36 1.48 1.62 0.96 6.74

8.74 35.3

9.70

2.48

19.74

14.3 3.08 7.33

16.3

16.6 1.81

21.2 1.46

3.49 4.7 2.50

4.18 5.0 2.60

5.5 ⫺0.6

top of rh base of rh

8.00

1.1 21.00 13.1 20.5 17.6

18.4

17.2

29.2

31.6

8.73 23.9

4.72 5.6 2.80

5.7

9.8 2.23

3.23

2.13 2.44

1.99 1.70

0.01 1.60

13.22

14.07

15.07

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(McGHP)

8.84

INTERACTIVE

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SECTION 8

TABLE 8.12 Cumulative Formation Constants for Metal Complexes with Inorganic Ligands (Continued)

Palladium(II) Platinum(II) Plutonium(III) Silver(I) Thallium(I) Thallium(III) Thorium Tin(II) Tin(IV) Uranium(IV) Uranium(VI) Zinc Zirconium Cyanide Cadmium Copper(I) Gold(I) Iron(II) Iron(III) Mercury(II) Nickel Silver(I) Zinc Fluoride Aluminum Beryllium Cerium(III) Chromium(III) Gadolinium Gallium Indium Iron(III) Lanthanum Magnesium Manganese(II) Plutonium(III) Scandium Thallium(I) Thallium(III) [TlO⫹ ] Thorium Titanium(IV) [TiO2⫹ ] Uranium(VI) Yttrium Zirconium Hydroxide Aluminum Antimony(III) Arsenic [as AsO⫹ ] Beryllium Bismuth(III) Cadmium Cerium(III) Cerium(IV)

log K1

log K2

6.1

10.7 11.5

1.17 3.04 0.52 8.14 1.38 1.51

log K3

log K4

13.1 14.5

15.7 16.0

5.04 13.60 0.38 2.24

log K5

cap height base of text

log K6

5.30 15.78

18.00

2.03

1.48 4

0.8 0.22 0.43 0.9 5.48

0.61 1.3

0.53 1.5

0.20 1.2

10.60 24.0 38.3

15.23 28.59

18.78 30.30 35 42

6.10 5.1 3.20 4.41 3.46 5.08 3.70 5.28 2.77 1.30 5.48 6.77

21.1

21.7

11.15 8.8

15.00 12.6

7.81

10.29

6.25 9.30

8.60 12.06

41.4 31.3 20.6 16.7 17.75

19.37

19.84

9.70

17.3 0.1 6.44 7.65 5.4 4.59 4.81 8.80

13.46 9.8 7.93 8.54 16.12

17.97 13.7 10.47 12.14 21.94

24.3 18.73 14.0 15.8 8.33

36.7 20.60 15.2

9.27 14.33 9.7 12.7 4.17 14.6 13.28

26.46

9.02

18.0 11.84

33.03 38.3 21.20 35.2 8.62

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.85

TABLE 8.12 Cumulative Formation Constants for Metal Complexes with Inorganic Ligands (Continued)

Chromium(III) Copper(II) Dysprosium Erbium(III) Gadolinium Gallium Indium Iodine Iron(II) Iron(III) Lanthanum Lead(II) Lutetium Magnesium Manganese(II) Neodymium Nickel Praseodymium Plutonium(III) Plutonium(IV) Plutonium [as PuO 22⫹ ] Samarium(III) Scandium Tellurium(IV) Thallium(III) Titanium(III) Uranium(IV) Uranium(VI) [as UO 22⫹ ] Vanadium(III) Vanadium(IV) [as VO 2⫹ ] Vanadium(V) [as VO 3⫹ ] Yttrium Zinc Zirconium Iodide Bismuth Cadmium Copper(I) Indium Iodine Iron(III) Lead Mercury(II) Silver Thallium(I) Thallium(III) Iodate Barium Calcium Magnesium Strontium Thorium

log K1

log K2

log K3

log K4

10.1 7.0 5.2 5.4 4.6 11.0 9.9 9.49 5.56 11.87 3.3 7.82 6.6 2.58 3.90 5.5 4.97 4.30 7.0 12.39 8.3 4.8 8.9

17.8 13.68

17.00

29.9 18.5

21.7 19.8 11.24 9.77 21.17

34.3 28.7 9.67 29.67

10.85

14.58

8.55

16.6

40.3

8.58

61.0

11.33

20.9

53.0

64.8

72.0

41.2 22.80 21.6

32.4 [25.8 for V2O4(OH)⫺ ] 46.2

11.30 28.3

14.14 41.9

17.66 55.3

4.49

14.95 5.41

1.00 2.89 1.88 2.00 12.87 6.58 0.72 11.41

3.43 8.85 2.26 5.79 3.15 23.82 11.74 0.90 20.88

3.92 27.60 13.68 1.08 27.60

1.05 0.89 0.72 1.00 2.88

4.79

7.15

3.63 2.10

38.0

25.37

25.2 5.0 4.40 14.3

log K6

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8.3

41.6 12.86 12.71 13.3 9.5 11.1 8.6

log K5

top of rh base of rh

58.5

16.80

18.80

4.47 29.83

31.82

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TABLE 8.12 Cumulative Formation Constants for Metal Complexes with Inorganic Ligands (Continued) log K1 Nitrate Barium Beryllium Bismuth(III) Cadmium Calcium Cerium(III) Curium(III) Hafnium Iron(III) Lanthanum Lead Mercury(II) Neodymium Neptunium(IV) Plutonium(III) Plutonium(IV) Strontium Thallium(I) Thallium(III) Thorium Uranium(IV) Uranium(VI) Ytterbium Zirconium [as ZrO 2⫹ ] Pyrophosphate Barium Calcium Cadmium Copper(II) Lead Magnesium Nickel Strontium Yttrium Zirconium Sulfate Cerium(III) Erbium Gadolinium Holmium Indium Iron(III) Lanthanum Neodymium Nickel Plutonium(IV) Praseodymium Samarium Thorium Uranium(IV) Uranium(VI)

0.92 1.62 1.26 0.40 0.28 1.04 0.57 0.92 1.0 0.26 1.18 0.35 0.52 0.38 0.77 0.54 0.82 0.33 0.92 0.78 0.20 0.34 0.45

4.6 4.6 5.6 6.7 5.7 5.8 4.7

log K2

log K3

log K4

log K5

log K6

2.43

4.32

6.40

8.48

10.29

0.69

1.27

cap height base of text

2.55

1.18 1.93

3.09

1.89 0.37 0.45 1.30 1.91

2.89

3.63

2.42 3.54

9.0 5.3 7.4 9.7 6.5

3.40 3.58 3.66 3.58 1.78 2.03 3.64 3.64 2.4 3.66 3.62 3.66 3.32 3.24 1.70

1.88 2.98

5.50 5.42 2.45

2.36

3.30

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.87

TABLE 8.12 Cumulative Formation Constants for Metal Complexes with Inorganic Ligands (Continued)

Yttrium Ytterbium Zirconium Sulfite Copper(I) Mercury(II) Silver Thiocyanate Bismuth Cadmium Chromium(III) Cobalt(II) Copper(I) Gold(I) Indium Iron(III) Mercury(II) Nickel Ruthenium(III) Silver Thallium(I) Uranium(IV) Uranium(VI) Vanadium(III) Vanadium(IV) Zinc Thiosulfate Cadmium Copper(I) Iron(III) Lead Mercury(II) Silver

log K1

log K2

3.47 3.58 3.79

6.64

7.77

8.5 22.66 7.35

9.2

2.26 1.98 2.98 ⫺0.70 5.18 23 3.00 3.36 17.47 1.64

3.41 2.58

4.23 3.6

0

3.00

7.57

9.08

2.11 0.74

1.18

6.44 12.22

13.84

7.5 5.30 1.15 1.39 1.87 ⫺0.04 12.11 2.58 2.95 1.18 1.78 0.80 1.49 0.76 2.0 0.92 1.62 3.92 10.27 2.10

8.82

5.13 29.44 13.46

log K3

log K4

log K5

top of rh base of rh cap height base of text

log K6

42 4.63 21.23 1.81

6.35 31.90

10.08

33.24

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TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands Temperature is 25⬚C and ionic strengths are approaching zero unless indicated otherwise: (a) At 20⬚C, (b) at 30⬚C, (c) 0.1 M uni-univalent salt, (d) 1.0 M uni-univalent salt, (e) 2.0 M uni-univalent salt present.

Acetate Ag(I) Ba(II) Ca(II) Cd(II) Ce(III) Co(II) Cr(III) Cu(II) a Fe(II) c Fe(III) a,d In(III) Hg(II) La(III) a,e Mg(II) Mn(II) Ni(II) Pb(II) Rare earths a,e Sr(II) Tl(III) UO2(II) a,e Y(III) a,e Zn(II) Acetylacetone Al(III) b Be(II) Cd(II) Ce(III) Cr(II) Co(II) Cu(II) Dy(III) b Er(III) b Eu(III) b Fe(II) Fe(III) Ga(III) Gd(III) b Hf(IV) Ho(III) In(III) La(III) b Lu(III) b Mg(II) Mn(II) Mn(III) Nd(III) Ni(II) a

log K1

log K2

0.73 0.41 0.6 1.5 1.68 1.5 1.80 2.16 3.2 3.2 3.50

0.64

log K3

log K4

2.3 2.69 1.9 4.72 3.20 6.1

2.4 3.13

5.95 8.43 2.48

7.90

9.08

2.98

2.95

2.06 1.81 4.0 2.8– 3.0

6.4 3.3– 3.7

8.5

2.38 1.53 1.5

4.36 2.65

6.34 3.38

8.6 7.8 3.84 5.30 5.9 5.40 8.27 6.03 5.99 5.87 5.07 11.4 9.5 5.90 8.7 6.05 8.0 5.1 6.23 3.65 4.24

15.5 14.5 6.66 9.27 11.7 9.54 16.34 10.70 10.67 10.35 8.67 22.1 17.9 10.38 15.4 10.73 15.1 8.90 11.00 6.27 7.35

5.6 6.06

9.9 10.77

1.56 0.8 9.84 1.12 2.52 1.6– 1.9 0.44

3.18

8.3

15.4

12.65

14.04 14.09 13.64 26.7 23.6 13.79 21.8 14.13

28.1

11.90 13.63

3.86 13.1 13.09

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(McGHP)

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INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.89

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1 Pd(II) b Pr(III) b Pu(IV) c Sc(III) b Sm(III) b Tb(III) b Th(IV) Tm(IV) b U(IV) a,c UO2(II) b VO(II) V(II) Y(III) b Yb(III) b Zn(II) b Zr(IV) Alizarin red Cr(VI) Cu(II) Hf(IV) Mo(VI) Pb(II) Th(IV) UO2(II) V(V) W(VI) Arsenazo Hf(IV) Zr(IV) Aurintricarboxylic acid Be(II) Cu(II) Fe(III) Th(IV) UO2(II) Benzoylacetone (75% dioxane) Ba(II) Be(II) Cd(II) Ce(III) Co(II) Cu(II) La(III) Mg(II) Mn(II) Ni(II) Pb(II) Pr(III) UO2(II) Y(III) Zn(II)

16.2 5.4 10.5 8.0 5.9 6.02 8.8 6.09 8.6 7.74 8.68 5.4 6.4 6.18 4.98 8.4

log K2 27.1 9.5 19.7 15.2 10.4 10.63 16.2 10.85 17.0 14.19 15.79 10.2 11.1 11.04 8.81 16.0

log K3

12.5 28.1

14.04 22.5 14.33 23.4

top of rh base of rh cap height base of text

log K4

34.1

26.7 29.5

14.7 13.9 13.64 23.2

30.1

4.7 4.1 10.4 9.6 6.0 8.24 4.22 8.6 7.8 10.07 12.95 4.54 4.1 4.68 5.04 4.77

12.59 7.79 10.09 9.42 12.05 6.33 7.69 8.66 9.58 8.84 7.02 12.15 8.24 9.62

8.81

9.4 24.01 14.36 19.42 17.83 23.01 11.66 14.09 15.78 18.00 16.35 13.62 23.27 14.98 17.90

27.04

16.78

18.74 20.57

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LEFT

(McGHP)

8.90

INTERACTIVE

top of rh base of rh

SECTION 8

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1 Calmagite Ca Mg

log K2

log K4

6.05 8.05 Complex of HL2⫺ Anion log K1

Citric acid Ag Al Ba Be Ca Cd Ce(III) Co(II) Cu(II) Eu(III) Fe(II) Fe(III) La Mg Mn(II) Nd(III) Ni Pb Pr Ra Sr Tl(I) UO2 Y Yb Zn

log K3

cap height base of text

Complex of L3⫺ Anion

log K2

log K1

7.1 7.0 2.98 4.52 4.68 3.98

Complex of H 2 L⫺

log K2

log K3

9.65

3.2

20.0

11.3 6.18

4.8 4.35

12.5 14.2 6.46

9.80

3.08 12.5

15.5 25.0 6.97

9.45

6.22

3.29 3.67 6.32

9.70

5.11 6.50

14.3 3.4

2.36 2.8 1.04 8.5

10.8 3.6 8

4.71 log K1

11.4 log K2

1,2-Diaminocyclohexane-N,N,N⬘,N⬘-tetraacetic acid Al c 17.63 Ba c 8.64 Ca c 12.3 Cd c 19.88 Ce(III) c 16.76 Co(II) c 19.57 Cu(II) c 21.95 Dy(III) c 19.69 Er(III) c 20.20 Eu(III) c 18.77 Fe(III) c 27.48 Ga c 22.91

log K3

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(McGHP)

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.91

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1 Gd c 18.80 Hg(II) c 24.4 Ho c 19.89 La c 16.35 Lu c 21.51 Mg c 10.41 Mn(II) c 17.43 Nd c 17.69 Ni c 19.4 Pb c 20.33 Pr c 17.23 Sm(III) c 18.63 Sr c 8.92 Tb c 19.30 Tm c 20.46 VO(II) c 19.40 Y c 19.41 Yb c 20.80 Zn c 18.6 Dibenzoylmethane (75% dioxane) Ba 6.10 Be 13.62 Ca 7.17 Cd 8.67 Ce(III) 10.99 Co(II) 10.35 Cu(II) 12.98 Cs 3.42 Fe(II) 11.15 K 3.67 Li 5.95 Mg 8.54 Mn(II) 9.32 Na 4.18 Ni 10.83 Pb 9.75 Rb 3.52 Sr 6.40 Zn 10.23 log K1 4,5-Dihydroxybenzene-1,3-disulfonic acid (Tiron) Al 19.02 Ba 4.10 Ca 5.80 Cd d 7.69 Ce(III) Co(II) d 8.19 Cu(II) d 12.76

log K2

11.50 26.03 13.55 16.63 21.53 20.05 24.98

log K3

top of rh base of rh cap height base of text

log K4

30.38

21.50

16.21 17.79 20.72 18.79 12.10 19.65 log K2

log K3

31.10

33.5

log Kf [MHL]

14.6 14.8 13.29 3.75 14.41 23.73

15.7 18.1

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LEFT

(McGHP)

8.92

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SECTION 8

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued)

Fe(III) a,c La Mg a,c Mn(II) c Ni a,c Pb d Sr c UO2(II) c VO(II) Zn d

log K1

log K2

log K3

log Kf [MHL]

20.7 12.9 6.86 8.6 8.56 11.95 4.55 15.90 15.88 9.00

35.9

46.9

22.6 18.6 [La(OH)L] 14.6

14.90 18.28

15.6

16.91

15.9

log K1

log K2

2,3-Dimercaptopropan-1-of (BAL) Fe(II) 15.8 Fe(III) 30.6 [Fe(OH)L] Mn(II) 5.23 Ni Zn 13.48 log K1 Dimethylglyoxime (50% dioxane) Cd 5.7 Co(II) 9.80 Cu(II) 12.00 Fe(II) La 6.6 Ni 11.16 Pb 7.3 Zn 7.7 2,2⬘-Dipyridyl Ag 3.65 Cd 4.26 Co(II) 5.73 Cr(II) 4.5 Cu(I) Cu(II) 8.0 Fe(II) 4.36 Hg(II) 9.64 Mg 0.5 Mn(II) d 4.06 Ni 6.80 Pb 3.0 Ti(III) V(II) 4.9 Zn 5.30 Eriochrome Black T Ca 5.4 Mg 7.0 Zn 13.5

cap height base of text

log Kf [M2L3]

28 10.43 22.78 23.3 log K2

40.6 log K3

log K4

10.7 18.94 33.44 7.25 12.5

13.9 7.15 7.81 11.57 10.5 14.2 13.60 8.0 16.74

10.47 17.59 14.0 17.08 17.45 19.54

7.84 13.26

11.47 18.46

9.6 9.83

25.28 13.1 13.63

20.6

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(McGHP)

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.93

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1 Ethanolamine Ag 3.29 Cu(II) Hg(II) 8.51 Ethylenediamine Ag 4.70 Cd a 5.47 Co(II) 5.91 Co(III) 18.7 Cr(II) 5.15 Cu(I) Cu(II) 10.67 Fe(II) 4.34 Hg(II) 14.3 Mg 0.37 Mn(II) 2.73 Ni 7.52 Pd(II) V(II) 4.6 Zn 5.77 Ethylenediamine-N, N, N⬘, N⬘-tetraacetic acid Ag 7.32 Al 16.11 Am(III) 18.18 Ba 7.78 Be 9.3 Bi 22.8 Ca 11.0 Cd 16.4 Ce(III) 16.80 Cf(III) 19.09 Cm(III) 18.45 Co(II) 16.31 Co(III) 36 Cr(II) 13.6 Cr(III) 23 Cu(II) 18.7 Dy 18.0 Er 18.15 Eu(III) 17.99 Fe(II) 14.33 Fe(III) 24.23 Ga 20.25 Gd 17.2 Hg(II) 21.80 Ho 18.1 In 24.95 La 16.34 Li 2.79 Lu 19.83 Mg 8.64 Mn(II) 13.8 Mo(V) 6.36

log K2

log K3

6.92 6.68 17.32 7.70 10.09 10.64 34.9 9.19 10.8 20.00 7.65 23.3 4.79 13.84 26.90 7.5 10.83

top of rh base of rh cap height base of text

log K4

16.48

12.09 13.94 48.69

21.0 9.70

5.67 18.33 8.8 14.11

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(McGHP)

8.94

INTERACTIVE

top of rh base of rh

SECTION 8

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1 Na Nd Ni Pb Pd(II) Pm(III) Pr Pu(III) Pu(IV) Pu(VI) Ra Sc Sm Sn(II) Sr Tb Th Ti(III) TiO(II) Tl(III) Tm U(IV) V(II) V(III) VO(II) V(V) Y Yb Zn Zr Glycine Ag Ba Be Ca Cd Co(II) Cu(II) Dy Er Fe(II) a Fe(III) a,d Gd Hg(II) La Mg Mn(II) Ni Pb Pd(II) Pr Sm

log K2

log K3

cap height base of text

log K4

1.66 16.6 18.56 18.3 18.5 17.45 16.55 18.12 17.66 17.66 7.4 23.1 16.43 22.1 8.80 17.6 23.2 21.3 17.3 22.5 19.49 17.50 12.70 25.9 18.0 18.05 18.32 18.70 16.4 19.40 3.41 0.77

6.89 4.95

1.38 4.74 5.23 8.60

4.3 10.0 10.3 3.44 3.6 6.18 5.47 9.12

8.60 9.25 15.54 12.2 12.7 7.8 11.9 19.2 11.2 6.46 6.6 11.14 8.92 17.55 11.5 11.7

10.76 16.27

15

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(McGHP)

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INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.95

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1

log K2

Sr 0.91 Y 12.5 Yb 13.0 Zn 5.52 9.96 N⬘-(2-Hydroxyethyl)ethylenediamine-N,N,N⬘-triacetic acid Ba c 5.54 Ca c 8.43 Cd c 13.0 Ce(III) c 14.11 Co(II) c 14.4 Cu(II) c 17.40 Dy c 15.30 Er c 15.42 Eu(III) c 15.35 Fe(II) c 11.6 Fe(III) c 19.8 Gd c 15.22 Hg(II) c 20.1 Ho c 15.32 La c 13.46 Lu c 15.88 Mg c 5.78 Mn(II) c 10.7 Nd c 14.86 Ni c 17.0 Pb c 15.5 Pr c 14.61 Sm c 15.28 Sr c 6.92 Tb c 15.32 Th c 18.5 Tm c 15.59 Y c 14.65 Yb c 15.88 Zn c 14.5 8-Hydroxy-2-methylquinoline (50% dioxane) Cd 9.00 9.00 Ce(III) 7.71 Co(II) 9.63 18.50 Cu(II) 12.48 24.00 Fe(II) 8.75 17.10 Mg 5.24 9.64 Mn(II) 7.44 13.99 Ni 9.41 17.76 Pb 10.30 18.50 UO2(II) 9.4 17 Zn 9.82 18.72 8-Hydroxyquinoline-5-sulfonic acid Ba 2.31 Ca 3.52 Cd 7.70 14.20 Ce(III) 6.05 11.05

log K3

top of rh base of rh cap height base of text

log K4

16.60

14.95

short standard long

DEAN #37261

LEFT

(McGHP)

8.96

INTERACTIVE

top of rh base of rh

SECTION 8

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued)

Co(II) Cu(II) Er Fe(II) Fe(III) Gd La Mg Mn(II) Nd Ni Pb Pr Sm Sr Th UO2(II) Zn Lactic acid Ba Ca Cd Ce(III) a,c Co(II) Cu(II) Er Eu(III) Fe(III) Gd Ho La a,c Li Mg Mn(II) Nd Ni Pb Pr a,c Rare earths a,c Sm Sr Tb Y Yb Zn Nitrilotriacetic acid Al Ba a Ca Cd c Ce(III) c

log K1

log K2

log K3

8.11 11.92 7.16 8.4 11.6 6.64 5.63 4.79 5.67 6.3 9.57 8.53 6.17 6.58 2.75 9.56 8.52 8.65

15.05 21.87 13.34 15.7 22.8 12.37 10.13 8.19 10.72 11.6 18.27 16.13 11.37 12.28

20.41

18.29 15.67 16.15

25.92

4.73

5.96

4.85 5.11 4.60

6.70 5.88

4.63 4.97 4.34

5.91 6.55 5.64

4.37

5.60

3.80 4.90 4.9– 5.4 4.58

6.10 6.1– 7.8 5.90

0.64 1.42 1.70 2.76 1.90 3.02 2.77 2.53 7.1 2.53 2.71 2.60 0.20 1.37 1.43 2.47 2.22 2.40 2.85 2.8– 3.0 2.56 0.98 2.61 2.53 2.85 2.20 ⬎10 5.88 7.60 9.80 10.83

4.73 4.70 5.27 3.75

cap height base of text

log K4

18.56 21.75 35.65 17.27 13.83

16.0 22.9 15.67 17.04 32.04

6.01 6.12 7.96

11.61 15.2 18.67

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(McGHP)

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INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.97

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1 Co(II) c 10.38 Cr(III) ⬎10 Cu(II) c 13.10 Dy c 11.74 Er c 12.03 Eu(III) c 11.52 Fe(II) c 8.84 Fe(III) c 15.87 Gd c 11.54 Hg(II) 12.7 Ho c 11.90 In 15 La c 10.36 Li a 3.28 Lu c 12.49 Mg c 5.36 Mn(II) 8.60 Na 2.15 Nd c 11.26 Ni 11.26 Pb a,c 11.8 Pr c 11.07 Sm(III) c 11.53 Sr 6.73 Tb c 11.59 Tl(I) 3.44 Th c 12.4 Tm c 12.22 Y c 11.48 Yb c 12.40 Zn c 10.45 Zr c 20.8 1-Nitroso-2-naphthol (75% dioxane) Ag 7.74 Cd 6.18 Co(II) 10.67 Cu(II) 12.52 Mg 6.2 Nd 9.5 Ni 10.75 Pb 9.73 Pr 9.04 Th c 8.50 Y 9.02 Zn 9.32 Zr 3.6 Oxalate Ag 2.41 Al 7.26 Am(III) Ba 2.31

log K2

log K3

top of rh base of rh cap height base of text

log K4

14.5

21.15 21.29 20.70 24.32 20.80 21.25 17.60 21.91 10.2 11.1 19.73 16.0 19.25 20.53 20.97

21.45 20.43 21.69 13.45

11.38 22.81 23.37 10.60 17.7 21.29 17.31 17.06 16.13 17.74 17.02

13.0 9.8

25.6 28.09 23.85 24.03 25.04

30.29

16.3 [Am(HL)⫺4 11.0]

short standard long

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(McGHP)

8.98

INTERACTIVE

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SECTION 8

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued)

Be Ca Cd Ce(III) Co(II) Co(III) Cu(II) Er Fe(II) Fe(III) Gd Hg(II) Mg Mn(II) Mn(III) e Mo(III) Mo(VI) Nd Ni NpO2(II) Pb Pu(III) Pu(IV) PuO2(II) Sr Th TiO(II) Tl(I) UO2(II) VO(II) V(II) Y Yb Zn Zr 1,10-Phenanthroline Ag Ca Cd Co(II) Cu(II) Fe(II) Fe(III) Hg(II) Mg Mn(II) Ni Pb VO(II) Zn

log K1

log K2

4.90 3.0 3.52 6.52 4.79

5.77 10.5 6.7

6.16 4.82 2.9 9.4 7.04 3.43 3.97 9.98 3.38 7.21 5.3 3.30 9.31 8.74

log K3

log K4

11.3 9.7 ⬃20

8.5 8.21 4.52 16.2

10.03 5.22 20.2

6.98 4.38 5.80 16.57

19.42

11.5 7.64 7.07 6.54 18.70 16.91 11.4

cap height base of text

⬎14 ⬃8.5

28 23.39

[MoO3(L)2⫺ 13.0]

27.50

2.54 24.48 2.67 2.03 10.57 9.80 ⬃2.7 6.52 7.30 4.89 9.80 5.02 0.7 5.93 7.25 9.08 5.85 6.5 1.2 3.88 8.80 4.65 5.47 6.55

10.10 11.7 7.60 17.14

11.47 ⬎14 8.15 20.86

21.15

12.07 10.53 13.95 15.76 11.45 11.4 19.65

14.31 19.90 20.94 21.3 23.5 23.35

7.04 17.10 7.5 9.69 12.35

10.11 24.80 9 17.55

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(McGHP)

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.99

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1 Phthalic acid Ba Ca Cd Co(II) Cu(II) La Ni Pb d UO2(II) Zn Piperidine Ag Hg(II) Pt(II) Propylene-1,2-diamine Cd b,c Co(II) d Cu(II) c Hg(II) c Ni d Zn b,c Pyridine Ag Cd Co(II) Cu(I) Cu(II) Fe(II) Hg(II) Mn(II) VO(II) Zn Pyridine-2,6-dicarboxylic acid Ba a,d Ca a,d Cd a,d Ce(III) a,d Co(II) a,d Cu(II) a,d Dy a,d Er a,d Eu(III) a,d Fe(II) a,d Fe(III) a,d Gd a,d Ho a,d La a,d Lu a,d

2.33 2.43 2.5 1.81 3.46

log K2

log K3

log K4

log K5 5.7

log K6 8.2

top of rh base of rh cap height base of text

4.51 4.83 7.74

2.14 3.4 4.38 2.2 3.30 8.70

5.42 6.41 10.78 7.43 5.89 1.97 1.40 1.14

2.59 0.71 5.1 1.92 ⫺1.70 1.41 3.46 4.6 5.7 8.34 7.0 9.14 8.69 8.77 8.84 5.71 10.91 8.74 8.72 7.98 9.03

6.48 17.44

9.97 11.47 20.06 23.53 13.62 10.87 4.35 1.95 1.54 3.34

12.12 14.72 23.25 17.89 12.57

2.27 4.51

2.50 5.44 log K6 6.89 6.54 log K6 10.2

4.33

5.93 log K5 7.00

10.0 2.77

10.4 3.37

3.50

1.11

1.61

1.93

7.2 10.0 14.42 12.5 16.52 16.19 16.39 15.98 10.36 17.13 16.06 16.23 13.79 16.80

18.80

22.14 22.14 21.00

21.83 22.08 18.06 21.48

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(McGHP)

8.100

INTERACTIVE

top of rh base of rh

SECTION 8

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1

log K2

Hg(II) a,d 20.28 Mg a,d 2.7 Mn(II) a,d 5.01 Nd a,d 8.78 Ni a,d 6.95 Pb a,d 8.70 Pr a,d 8.63 Sm a,d 8.86 Sr a,d 3.89 Tb a,d 8.68 Tm a,d 8.83 Y a,d 8.46 Yb a,d 8.85 Zn a,d 6.35 1-(2-Pyridylazo)-2-naphthol (PAN) Co(II) ⬎12 Cu(II) 16 Mn(II) 8.5 Ni 12.7 Tl(III) 2.29 Zn 11.2

8.49 15.60 13.50 10.60 15.10 15.88 16.11 16.54 15.73 16.61 11.88

log K4

20.66

19.94 21.23 22.03 22.04 21.34 21.83

16.4 25.3 21.7 log Kf [ML]

4-(2-Pyridylazo)resorcinal (PAR) Co(II) Cu(II) Mn(II) Ni Sc Tl(III) Zn

log K3

cap height base of text

log Kf [MHL]

log Kf [M(HL)2 ]

⬎12 10.3 9.7 13.2

18.9 26.0

12.4

23.5

log Kf [M2L]

log Kf [MHL]

4.8 4.23

log Kf [ML] Pyrocatechol-3,5-disulfonate (Pyrocatechol Violet) Al 19.13 Bi 27.07 Cd 8.13 Co(II) 9.01 Cu(II) 16.47 Ga 22.18 In 18.10 Mg 4.42 Mn(II) 7.13 Ni 9.35 Pb 13.25 Th 23.36 Zn 10.41 Zr 27.40

4.95 5.25 5.86 6.53 11.18 4.65 4.81 4.6 4.38 4.42 6.21 4.18

3.66 5.36 6.85 10.19 7.21

short standard long

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(McGHP)

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.101

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1 8-Quinolinol Ba Be Ca (75% dioxane) Cd Ce(III) (50% dioxane) Co(II) Cu(II) Fe(II) Fe(III) La Mg (50% dioxane) Mn(II) (50% dioxane) Ni (50% dioxane) Pb (50% dioxane) Sm Sr Th UO2(II) (50% dioxane) V(II) VO(II) Y Zn (50% dioxane)

2.07 3.36 7.3 7.2 9.15 9.1 12.2 8.58 12.3 5.85 6.38 8.28 11.44 10.61 6.84 2.89 10.45 11.25 12.8 10.97 8.15 9.96

Salicylaldoxime Ba Be Ca Cd Co(II) Cu(II) Mg Ni Sr Zn

log K3

13.2 13.4 17.13 17.2 23.4 16.93 23.6 16.95 11.81 15.45 21.38 18.70

22.23 33.9

cap height base of text

log K4

19.50 6.08 20.40 20.89 23.6 20.19 14.90 18.86

29.85

38.80

20.25

log Kf [MHL⫹ ]

log Kf [M(HL)2 ]

0.53 ⬍7 0.92 ⬍4.4

3.72 3.72 8.13 8.13 4.10 3.77 3.77

0.64 ⬍5.2 log K1

Salicylic acid Al Be Cd Ce(III) Co(II) Cr(II) Cu(II) Fe(II) Fe(III) a,c La

log K2

top of rh base of rh

14.11 17.4 5.55 2.66 6.72 8.4 10.60 6.55 16.48 2.64

log K2

log K3

11.42 15.3 18.45 11.25 28.12

36.80

log K4

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DEAN #37261

LEFT

(McGHP)

8.102

INTERACTIVE

top of rh base of rh

SECTION 8

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1 Mg (75% dioxane) Mn(II) Nd Ni Pr Th TiO(II) UO2(II) V(II) Zn Succinic acid Ba Be Ca Cd Co(II) Cu(II) Fe(III) Hg(II) La Mg Mn(II) Nd Ni Pb Ra Sr Zn 5-Sulfosalicylic acid Al c Be c Cd c Co(II) c Cr(II) c Cr(III) c Cu(II) c Fe(II) c Fe(III) c La c Mn(II) c NbO(III) c Ni c UO2(II) c Zn c Tartaric acid Ba Bi Ca Cd Co(II) Cu(II)

4.7 5.90 2.70 6.95 2.68 4.25 6.09 13.4 6.3 6.85

log K2

log K3

log K4

10.05

11.60

cap height base of text

9.80 11.75 7.60

2.08 3.08 2.0 2.2 2.22 3.33 7.49 7.28 3.96 1.20 2.26 8.1 2.36 2.8 1.0 1.06 1.6 13.20 11.71 16.68 6.13 7.1 9.56 9.52 5.90 14.64 9.11 5.24 4.0 6.42 11.14 6.05

22.83 20.81 29.08 9.82 12.9

28.89

16.45 25.18

32.12

8.24 7.7 10.24 19.20 10.65 1.62 8.30

2.98 2.8 2.1 3.2

9.01

5.11

4.78

6.51 log Kf 19.14 [Cu(OH)2L2⫺ ]

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DEAN #37261

(McGHP)

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.103

TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued)

Eu(III) Fe(III) La Mg Nd Pb Ra Sr Zn Thioglycolic acid Ce(III) a,c Co(II) Fe(II) Hg(II) La a,c Mn(II) Pb Ni Rare earths a,c Y a,c Zn Thiourea Ag Bi Cd Cu(I) Hg(II) Pb Ru(III) Thoron Th Triethanolamine Ag Co(II) Cu(II) Hg(II) Ni Zn Triethylenetetramine (Trien) Ag Cd Co(II) Cu(II) Fe(II) Fe(III) Hg(II) Mn(II) Ni Pb Zn

log K1

log K2

4.98 7.49 3.06

8.11

log K3

log K4

4.7

log Kf 14.1 [Pb(OH)2L2⫺ ]

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1.36 9.0 3.78 1.24 1.60 2.68 1.99 5.84

8.32 3.03 12.15 10.92 43.82 2.98 7.56

1.98 4.38 8.5 6.98 1.9– 2.1 1.91 7.86

13.53 3.0– 3.3 3.19 15.04

7.4

13.1

0.6

1.6

1.4 1.21

22.1 3.1

2.6 13 24.7 4.7 0.72

log K6 11.9 4.6 15.4 26.8 8.3

10.15 2.30 1.73 4.30 6.90 2.7 2.00 7.7 10.75 11.0 20.4 7.8 21.9 25.26 4.9 14.0 10.4 11.9

3.64

13.08

13.9

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TABLE 8.13 Cumulative Formation Constants for Metal Complexes with Organic Ligands (Continued) log K1

log K2

1,1,1-Trifluoro-3-2⬘-Thenoylacetone (TTA) Ba Cu(II) 6.55 Fe(III) 6.9 Ni 10.0 Pr 9.53 Pu(III) 9.53 Pu(IV) 8.0 Th 8.1 U(IV) 7.2 Zr 3.03 [as ZrL3⫹ ] Xylenol orange Bi 5.52 Fe(III) 5.70 Hf 6.50 Tl(III) 4.90 Zn 6.15 Zr 7.60 Zincon Zn 13.1

8.3 8.3.1

log K3

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log K4

10.6 13.0

BUFFER SOLUTIONS Standard Reference pH Buffer Solutions

The assigned values of pHs , according to the Bates-Guggenheim convention [Pure Applied Chem. 1:163 (1960)], for the primary standard solutions prepared from salts issued by the National Institute for Science and Technology (NIST, US) (U.S.) are given in Table 8.14. These are smoothed values. The ionic strength of these reference solutions is 0.1 or less. Strictly speaking the NIST scale uses a molality concentration system; however, values are given in molarity units for convenience. As a result of a variable liquid-junction potential, the measured pH may be expected to differ seriously from the paH determined from cells without a liquid junction in solutions of high acidity or high alkalinity. Merely to affirm the proper functioning of the glass electrode at the extreme ends of the pH scale, two secondary standards are included in Table 8.14. In addition, values for a 0.1 m solution of HCl are given to extend the pH scale up to 275⬚C [see R. S. Greeley, Anal. Chem. 32:1717 (1960)]: t, ⬚C: pH:

25 1.10

60 1.11

90 1.12

125 1.13

150 1.14

175 1.15

200 1.16

225– 275 1.2

Uncertainties in the values are ⫾0.03 pH unit from 25 to 90⬚C, ⫾0.05 pH unit from 125 to 200⬚C, and ⫾0.1 pH unit from 225 to 275⬚C.

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0 5 10 15 20

1.666 1.668 1.638 1.642 1.644

25 30 35 38 40

1.646 1.648

45 50 55 60

Dilution value ⌬pH1/2

3.557 3.552 3.549 3.548 3.547

1.660

3.547 3.549 3.554 3.560

1.671 1.689 1.72 1.73

3.580 3.609 3.650 3.674

⫹0.186

⫹0.049

1.653

0.05 M KH phthalate

0.025 M KH2PO4, 0.025 M Na2HPO4

0.0087 M KH2PO4, 0.0302 M Na2HPO4

0.01 M Na2B4O7

0.025 M NaHCO3, 0.025 M Na2CO3

Secondary standard Ca(OH)2 (saturated at 25⬚C)

3.860 3.840 3.820 3.802 3.788

4.003 3.999 3.997 3.998 4.002

6.984 6.951 6.923 6.900 6.881

7.534 7.500 7.472 7.448 7.429

9.464 9.395 9.332 9.276 9.225

10.317 10.245 10.179 10.118 10.062

13.423 13.207 13.003 12.810 12.627

3.776 3.766 3.759 3.756 3.753

4.005 4.011 4.018 4.030 4.035

6.865 6.853 6.844 6.840 6.838

7.413 7.400 7.389 7.384 7.380

9.180 9.139 9.102 9.088 9.068

10.012 9.966 9.925 9.910 9.889

12.454 12.289 12.133 12.043 11.984

4.047 4.050 4.075 4.081

6.834 6.833 6.834 6.836

7.373 7.367

9.038 9.011 8.985 8.962

4.116 4.164 4.205 4.227

6.845 6.859 6.877 6.886

⫹0.052

⫹0.080

3.749

0.024

9.828

11.841 11.705 11.574 11.449

8.921 8.885 8.850 8.833 ⫹0.070

⫹0.01

RIGHT

70 80 90 95

1.649 1.650

KH tartrate (saturated at 25⬚C)

0.05 M KH2 citrate

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Temperature ⬚C

Secondary standard 0.05 M K tetraoxalate

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TABLE 8.14 National Bureau of Standards (U.S.) Reference pH Buffer Solutions

0.079

⫺0.28

INTERACTIVE

Source: R. G. Bates, J. Res. Natl. Bur. Stand. (U.S.), 66A:179 (1962) and B. R. Staples and R. G. Bates, J. Res. Natl. Bur. Stand. (U.S.), 73A:37 (1969). Note: The uncertainty is ⫾0.003 in pH in the range 0–50⬚C, rising to ⫾0.02 above 70⬚C.

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TABLE 8.15 Compositions of Standard pH Buffer Solutions [National Bureau of Standards (U.S.)] Air weight of material per liter of buffer solution. Standard

Weight, g

KH3(C2O4)2 · 2H2O, 0.05M Potassium hydrogen tartrate, about 0.034M Potassium hydrogen phthalate, 0.05M Phosphate: KH2PO4, 0.025M Na2HPO4, 0.025M Phosphate: KH2PO4, 0.008665M Na2HPO4, 0.03032M Na2B4O7 · 10H2O, 0.01M Carbonate: NaHCO3, 0.025M Na2CO3, 0.025M Ca(OH)2, about 0.0203M

12.61 Saturated at 25⬚C 10.12 3.39 3.53 1.179 4.30 3.80 2.10 2.65 Saturated at 25⬚C

The buffer values for the NBS reference pH buffer solutions are given below:

Buffer solution

KH tartrate

0.05 M KH2 citrate

Buffer value ␤

0.027

0.034

0.05 M KH phthalate

0.025 M KH2PO4 , 0.25 M Na2HPO4

0.0087 M KH2PO4 , 0.0302 M Na2HPO4

0.01 M Na2B4O7

0.025 M NaHCO3 , 0.025 M Na2CO3

0.016

0.029

0.016

0.020

0.029

For the secondary pH reference standards, the buffer value is 0.070 for potassium tetroxalate and 0.09 for calcium hydroxide. To prepare the standard pH buffer solutions recommended by the National Bureau of Standards (U.S.), the indicated weights of the pure materials in Table 8.15 should be dissolved in water of specific conductivity not greater than 5 micromhos. The tartrate, phthalate, and phosphates can be dried for 2 h at 100⬚C before use. Potassium tetroxalate and calcium hydroxide need not be dried. Fresh-looking crystals of borax should be used. Before use, excess solid potassium hydrogen tartrate and calcium hydroxide must be removed. Buffer solutions pH 6 or above should be stored in plastic containers and should be protected from carbon doxide with soda-lime traps. The solutions should be replaced within 2 to 3 weeks, or sooner if formation of mold is noticed. A crystal of thymol may be added as a preservative. 8.3.2

Standards for pH Measurement of Blood and Biological Media

Blood is a well-buffered medium. In addition to the NBS phosphate standard of 0.025 M (pHs ⫽ 6.480 at 38⬚C), another reference solution containing the same salts, but in the molal ratio 1 : 4, has an ionic strength of 0.13. It is prepared by dissolving 1.360 g of KH2PO4 and 5.677 g of Na2HPO4 (air weights) in carbon dioxide-free water to make 1 liter of solution. The pHs is 7.416 ⫾ 0.004 at 37.5 and 38⬚C. The compositions and pHs values of tris(hydroxymethyl)aminomethane, covering the pH range 7.0 to 8.9, are listed in Table 8.16.

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TABLE 8.16 Composition and pH Values of Buffer Solutions Values based on the conventional activity pH scale as defined by the National Bureau of Standards (U.S.) and pertain to a temperature of 25⬚C [Ref: Bower and Bates, J. Research Natl. Bur. Standards (U.S.), 55:197 (1955) and Bates and Bower, Anal. Chem., 28:1322 (1956)]. Buffer value is denoted by column headed ␤. 25 ml 0.2M KCl ⫹ x ml 0.2M HCl, Diluted to 100 ml

50 ml 0.1M KH Phthalate ⫹ x ml 0.1M HCl, Diluted to 100 ml

50 ml 0.1M KH Phthalate ⫹ x ml 0.1M NaOH, Diluted to 100 ml

pH

x

␤

pH

x

␤

pH

x

␤

1.00 1.20 1.40 1.60 1.80 2.00 2.20

67.0 42.5 26.6 16.2 10.2 6.5 3.9

0.31 0.34 0.19 0.077 0.049 0.030 0.022

2.20 2.40 2.60 2.80 3.00 3.20 3.40 3.60 3.80

49.5 42.2 35.4 28.9 22.3 15.7 10.4 6.3 2.9

0.036 0.033 0.032 0.030 0.026 0.023 0.018 0.015

4.20 4.40 4.60 4.80 5.00 5.20 5.40 5.60 5.80

3.0 6.6 11.1 16.5 22.6 28.8 34.1 38.8 42.3

0.017 0.020 0.025 0.029 0.031 0.030 0.025 0.020 0.015

50 ml 0.1M Tris(hydroxymethyl)aminomethane ⫹ x ml 0.1M HCl, Diluted to 100 ml ⌬pH/⌬t ⯝ ⫺0.028 I ⫽ 0.001x

50 ml 0.1M KH2PO4 ⫹ x ml 0.1M NaOH, Diluted to 100 ml pH

x

␤

pH

x

␤

5.80 6.00 6.20 6.40 6.60 6.80 7.00 7.20 7.40 7.60 7.80 8.00

3.6 5.6 8.1 11.6 16.4 22.4 29.1 34.7 39.1 42.4 44.5 46.1

0.010 0.015 0.021 0.027 0.033 0.031 0.025 0.020 0.013 0.009

7.00 7.20 7.40 7.60 7.80 8.00 8.20 8.40 8.60 8.80 9.00

46.6 44.7 42.0 38.5 34.5 29.2 22.9 17.2 12.4 8.5 5.7

0.012 0.015 0.018 0.023 0.029 0.031 0.026 0.022 0.016

50 ml 0.025M Borax ⫹ x ml 0.1M HCl, Diluted to 100 ml ⌬pH/⌬t ⯝ ⫺0.008 I ⫽ 0.025

50 ml 0.025M Borax ⫹ x ml 0.1M NaOH, Diluted to 100 ml ⌬pH/⌬t ⯝ ⫺0.008 I ⫽ 0.001(25 ⫹ x)

50 ml of a Mixture 0.1M with Respect to Both KCl and H3BO3 ⫹ x ml 0.1M NaOH, Diluted to 100 ml pH

x

␤

8.00 8.20 8.40 8.60 8.80 9.00 9.20 9.40 9.60 9.80 10.00 10.20

3.9 6.0 8.6 11.8 15.8 20.8 26.4 32.1 36.9 40.6 43.7 46.2

0.011 0.015 0.018 0.022 0.027 0.029 0.027 0.022 0.016 0.014

50 ml 0.05M NaHCO3 ⫹ x ml 0.1M NaOH, Diluted to 100 ml ⌬pH/⌬t ⯝ ⫺0.009 I ⫽ 0.001(25 ⫹ 2x)

pH

x

␤

pH

x

␤

pH

x

␤

8.00 8.20 8.40 8.60 8.80

20.5 19.7 16.6 13.5 9.4

0.010 0.012 0.018 0.023

9.20 9.40 9.60 9.80 10.00

0.9 3.6 11.1 15.0 18.3

0.026 0.022 0.018 0.014

9.60 9.80 10.00 10.20 10.40

5.0 6.2 10.7 13.8 16.5

0.014 0.016 0.015 0.013

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TABLE 8.16 Composition and pH Values of Buffer Solutions (Continued) 50 ml 0.025M Borax ⫹ x ml 0.1M HCl, Diluted to 100 ml ⌬pH/⌬t ⯝ ⫺0.008 I ⫽ 0.025

50 ml 0.025M Borax ⫹ x ml 0.1M NaOH, Diluted to 100 ml ⌬pH/⌬t ⯝ ⫺0.008 I ⫽ 0.001(25 ⫹ x)

50 ml 0.05M NaHCO3 ⫹ x ml 0.1M NaOH, Diluted to 100 ml ⌬pH/⌬t ⯝ ⫺0.009 I ⫽ 0.001(25 ⫹ 2x)

pH

x

␤

pH

x

␤

pH

x

␤

9.00 9.10

4.6 2.0

0.026

10.20 10.40 10.60

20.5 22.1 23.3

0.009 0.007 0.005

10.60 10.80 11.00

19.1 21.2 22.7

0.012 0.009

25 ml 0.2M KCl ⫹ x ml 0.2M NaOH, Diluted to 100 ml ⌬pH/⌬t ⯝ ⫺0.033 I ⫽ 0.001(50 ⫹ 2x)

50 ml 0.05M Na2HPO4 ⫹ x ml 0.1M NaOH, Diluted to 100 ml ⌬pH/⌬t ⯝ ⫺0.025 I ⫽ 0.001(77 ⫹ 2x) pH

x

␤

pH

x

␤

11.00 11.20 11.40 11.60 11.80 11.90

4.1 6.3 9.1 13.5 19.4 23.0

0.009 0.012 0.017 0.026 0.034 0.037

12.00 12.20 12.40 12.60 12.80 13.00

6.0 10.2 16.2 25.6 41.2 66.0

0.028 0.048 0.076 0.12 0.21 0.30

The phosphate-succinate system gives the values of pHs shown below:

Molality Molality ⫽ KH2PO4 Na2HC6H5 O7

pHs

⌬(pHs /⌬t)

0.005 0.010 0.015 0.020 0.025

6.251 6.197 6.162 6.131 6.109

⫺0.000 86 deg⫺1 ⫺0.000 71 ⫺0.000 4

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TABLE 8.17 Standard Reference Values pH*s for the Measurement of Acidity in 50 Weight Percent Methanol-Water

Temperature, ⬚C

0.02m HOAc, 0.02m NaOAc, 0.02m NaCl

0.02m NaHSuc, 0.02m NaCl

0.02m KH2PO4 , 0.02m Na2HPO4 , 0.02m NaCl

10 15 20 25 30 35 40

5.560 5.549 5.543 5.540 5.540 5.543 5.550

5.806 5.786 5.770 5.757 5.748 5.743 5.741

7.937 7.916 7.898 7.884 7.872 7.863 7.858

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OAc ⫽ acetate Suc ⫽ succinate Reference: R. G. Bates, Anal Chem., 40(6):35A (1968).

TABLE 8.18 pH* Values for Buffer Solutions in Alcohol-Water Solvents at 25⬚C Liquid-junction potential not included. Solvent Composition (weight per cent alcohol)

0.01M H2C2O4 , 0.01M NH4HC2O4

0.01M H2Suc, 0.01M LiHSuc

0.01M HSal, 0.01M NaSal

Methanol-Water Solvents 0 10 20 30 40 50 60 70 80 90 92 94 96 98 99 100

2.15 2.19 2.25 2.30 2.38 2.47 2.58 2.76 3.13 3.73 3.90 4.10 4.39 4.84 5.20 5.79

4.12 4.30 4.48 4.67 4.87 5.07 5.30 5.57 6.01 6.73 6.92 7.13 7.43 7.89 8.23 8.75

7.53

Ethanol-Water Solvents 0 30 50 71.9 100

2.15 2.32 2.51 2.98

4.12 4.70 5.07 5.71 8.32

Suc ⫽ succinate

Sal ⫽ salicylate

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8.3.3

Buffer Solutions Other Than Standards

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The range of the buffering effect of a single weak acid group is approximately one pH unit on either side of the pKa . The ranges of some useful buffer systems are collected in Table 8.19. After all the components have been brought together, the pH of the resulting solution should be determined at the temperature to be employed with reference to standard reference solutions. Buffer components should be compatible with other components in the system under study; this is particularly significant for buffers employed in biological studies. Check tables of formation constants to ascertain whether metal-binding character exists.

TABLE 8.19 pH Values of Biological and Other Buffers for Control Purposes Materials p-Toluenesulfonate and p-toluenesulfonic acid Glycine and HCl Citrate and HCl Formate and HCl Succinate and borax Phenyl acetate and HCl Acetate and acetic acid Succinate and succinic acid 2-(N-Morpholino)ethanesulfonic acid Bis(2-hydroxyethyl)iminotris(hydroxymethyl)methane KH2PO4 and borax N-(2-Acetamido)-2-iminodiacetic acid 2-[(2-Amino-2-oxoethyl)amino]ethanesulfonic acid Piperazine-N,N⬘-bis(2-ethanesulfonic acid) 3-(N-Morpholino)-2-hydroxypropanesulfonic acid 1,3-Bis[tris(hydroxymethyl)methylamino]propane KH2PO4 and Na2HPO4 N,N-Bis(2-hydroxyethyl)-2-aminoethanesulfonic acid 3-(N-Morpholino)propanesulfonic acid N-(2-Hydroxyethyl)piperazine-N⬘-(2-ethanesulfonic acid) N-Tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid 3-[N,N-Bis(2-hydroxyethyl)amino]-2-hydroxypropanesulfonic acid 3-[N-tris(hydroxymethyl)methylamino]-2-hydroxypropanesulfonic acid 5,5-Diethylbarbiturate (veronal) and HCl Tris(hydroxymethyl)aminoethane N-(2-hydroxyethyl)piperazine-N⬘-(2-hydroxypropanesulfonic acid) Piperazine-N,N⬘-bis(2-hydroxypropanesulfonic acid) Triethanolamine N-Tris(hydroxymethyl)methylglycine Borax and HCl N,N-Bis(2-hydroxyethyl)glycine N-Tris(hydroxymethyl)methyl-3-aminopropanesulfonic acid 3-[(1,1-Dimethyl-2-hydroxyethyl)-2-hydroxypropanesulfonic acid Ammonia (aqueous) and NH4Cl 2-(N-Cyclohexylamino)-2-hydroxy-1-propanesulfonic acid

Acronym

pKa

pH range

1.7 2.35 3.13 3.71 4.21, 5.64 4.31 4.76 4.21, 5.64 6.1 6.5 2.2, 7.2; 9 6.6 6.8 6.8 6.9 6.8, 9.0

1.1– 3.3 1.0– 3.7 1.3– 4.7 2.8– 4.6 3.0– 5.8 3.5– 5.0 3.7– 5.6 4.8– 6.3 5.5– 6.7 5.8– 7.2 5.8– 9.2 6.0– 7.2 6.1– 7.5 6.1– 7.5 6.2– 7.6 6.3– 9.5

BES MOPS HEPES TES DIPSO TAPSO

7.2 7.1 7.2 7.5 7.5 7.6 7.6

6.1– 7.5 6.4– 7.8 6.5– 7.9 6.8– 8.2 6.8– 8.2 7.0– 8.2 7.0– 8.2

TRIZMA HEPPSO POPSO TEA TRICINE

8.0 8.1 7.8 7.8 7.8 8.1

7.0– 8.5 7.0– 9.1 7.1– 8.5 7.2– 8.5 6.9– 8.5 7.4– 8.8 7.6– 8.9 7.6– 9.0 7.7– 9.1 8.3– 9.7 8.3– 9.2 8.6– 10.0

MES BIS-TRIS ADA ACES PIPES MOPSO BIS-TRIS PROPANE

BICINE TAPS AMPSO CHES

8.3 8.4 9.0 9.2 9.3

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TABLE 8.19 pH Values of Biological and Other Buffers for Control Purposes (Continued) Materials

Acronym

Glycine and NaOH Ethanolamine (2-aminoethanol) and HCl 3-(Cyclohexylamino)-2-hydroxy-1-propanesulfonic acid 2-Amino-2-methyl-1-propanol Carbonate and hydrogen carbonate Borax and NaOH 3-(Cyclohexylamino)-1-propanesulfonic acid Na2HPO4 and NaOH x mL of 0.2M Sodium Acetate (27.199 g NaOAc · 3H2O per liter) plus y mL of 0.2M Acetic Acid

pH

NaOAc, mL

Acetic Acid, mL

3.60 3.80 4.00 4.20 4.40 4.60 4.80 5.00 5.20 5.40 5.60

7.5 12.0 18.0 26.5 37.0 49.0 60.0 70.5 79.0 85.5 90.5

92.5 88.0 82.0 73.5 63.0 51.0 40.0 29.5 21.0 14.5 9.5

x mL of Veronal (20.6 g Na Diethylbarbiturate per Liter) plus y mL of 0.1M HCl

pKa 9.7 9.5 9.6 9.7 10.3

CAPSO AMP

CAPS

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pH range 8.2– 10.1 8.6– 10.4 8.9– 10.3 9.0– 10.5 9.2– 11.0 9.4– 11.1 9.7– 11.1 11.0– 12.0

10.4 11.9

x mL of 0.1M KH2PO4 (13.617 g · L⫺1) plus y mL of 0.05M Borax Solution (19.404 g Na2B4O7 · 10H2O per Liter)

pH

KH2PO4 , mL

Borax, mL

pH

KH2PO4 , mL

Borax, mL

5.80 6.00 6.200 6.40 6.60 6.80 7.00 7.20 7.40

92.1 87.7 83.0 77.8 72.2 66.7 62.3 58.1 55.0

7.9 12.3 17.0 22.2 27.8 33.3 37.7 41.9 45.0

7.60 7.80 8.00 8.20 8.40 8.60 8.80 9.00 9.20

51.7 49.2 46.5 43.0 38.7 34.0 27.6 17.5 5.0

48.3 50.8 53.5 57.0 61.3 66.0 72.4 82.5 95.0

x mL of 0.2M Aqueous NH3 Solution plus y mL of 0.2M NH4Cl (10.699 g · L⫺1)

pH

Veronal, mL

HCl, mL

pH

Aq NH3 , mL

NH4Cl, mL

7.00 7.20 7.40 7.60 7.80 8.00 8.20 8.40 8.60 8.80 9.00

53.6 55.4 58.1 61.5 66.2 71.6 76.9 82.3 87.1 90.8 93.6

46.4 44.6 41.9 38.5 33.8 28.4 23.1 17.7 12.9 9.2 6.4

8.00 8.20 8.40 8.60 8.80 9.00 9.25 9.40 9.60 9.80 10.00

5.5 8.5 12.5 18.5 26.0 36.0 50.0 58.5 69.0 78.0 85.0

94.5 91.5 87.5 81.5 74.0 64.0 50.0 41.5 31.0 22.0 15.0

x mL of 0.1M Citrate (21.0 g Citric Acid Monohydrate ⫹ 200 mL 1M NaOH per Liter) plus y mL of 0.1M NaOH

pH

Citrate, mL

NaOH, mL

5.10 5.30 5.50 5.70 5.90

90.0 80.0 71.0 67.0 62.0

10.0 20.0 29.0 33.0 38.0

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TABLE 8.19 pH Values of Biological and Other Buffers for Control Purposes (Continued) x mL of 0.2M NaOH Added to 100 mL of Stock Solution (0.04M Acetic Acid, 0.04M H3PO4 , and 0.04M Boric Acid) pH

NaOH, mL

pH

NaOH, mL

pH

NaOH, mL

pH

NaOH, mL

1.81 1.89 1.98 2.09 2.21 2.36 2.56 2.87 3.29 3.78

0.0 2.5 5.0 7.5 10.0 12.5 15.0 17.5 20.0 22.5

4.10 4.35 4.56 4.78 5.02 5.33 5.72 6.09 6.37 6.59

25.0 27.5 30.0 32.5 35.0 37.5 40.0 42.5 45.0 47.5

6.80 7.00 7.24 7.54 7.96 8.36 8.69 8.95 9.15 9.37

50.0 52.5 55.0 57.5 60.0 62.5 65.0 67.5 70.0 72.5

9.62 9.91 10.38 10.88 11.20 11.40 11.58 11.70 11.82 11.92

75.0 77.5 80.0 82.5 85.0 87.5 90.0 92.5 95.0 97.5

x mL of 0.1M HCl plus y mL of 0.1M Glycine (7.505 g Glycine ⫹ 5.85 g NaCl per Liter)

pH

HCl, mL

Glycine, mL

1.20 1.40 1.60 1.80 2.00 2.20 2.40 2.60 2.80 3.00 3.30 3.60

84.0 71.0 61.8 55.2 49.1 42.7 36.5 30.3 24.0 17.8 10.8 6.0

16.0 29.0 38.2 44.8 50.9 57.3 63.5 69.7 76.0 82.2 89.2 94.0

x mL of 0.1M HCl plus y mL of 0.1M Citrate (21.008 g Citric Acid Monohydrate ⫹ 200 ml 1M NaOH per Liter)

pH

HCl, mL

Citrate, mL

3.50 3.60 3.80 4.00 4.20 4.40 4.60 4.80

52.8 51.3 48.6 43.8 38.6 34.6 24.3 11.0

47.2 48.7 51.4 56.2 61.4 65.4 75.7 89.0

x mL of 0.05M Succinic Acid (5.90 g · L⫺1) plus y mL of Borax Solution (19.404 g Na2B4O7 · 10H2O per Liter)

pH

Succinic Acid, mL

Borax, mL

3.60 3.80 4.00 4.20 4.40 4.60 4.80 5.00 5.20 5.40 5.60 5.80

90.5 86.3 82.2 77.8 73.8 70.0 66.5 63.2 60.5 57.9 55.7 54.0

9.5 13.7 17.8 22.2 26.2 30.0 33.5 36.8 39.5 42.1 44.3 46.0

x mL of 0.2M Na2HPO4 · 2H2O (35.599 g · L⫺1) plus y mL of 0.1M Citric Acid (19.213 g · L⫺1)

pH

Na2HPO4 , mL

Citric Acid, mL

pH

Na2HPO4 , mL

Citric Acid, mL

pH

Na2HPO4 , mL

Citric Acid, mL

2.20 2.40 2.60 2.80 3.00 3.20 3.40 3.60 3.80 4.00

2.00 6.20 10.90 15.85 20.55 24.70 28.50 32.20 35.50 38.55

98.00 93.80 89.10 84.15 79.45 75.30 71.50 67.80 64.50 61.45

4.20 4.40 4.60 4.80 5.00 5.20 5.40 5.60 5.80 6.00

41.40 44.10 46.75 49.30 51.50 53.60 55.75 58.00 60.45 63.15

58.60 55.90 53.25 50.70 48.50 46.40 44.25 42.00 39.55 36.85

6.20 6.40 6.60 6.80 7.00 7.20 7.40 7.60 7.80 8.00

66.10 69.25 72.75 77.25 82.35 86.95 90.85 93.65 95.75 97.25

33.90 30.75 27.25 22.75 17.65 13.05 9.15 6.35 4.25 2.75

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When there are two or more acid groups per molecule, or a mixture is composed of several overlapping acids, the useful range is larger. Universal buffer solutions consist of a mixture of acid groups which overlap such that successive pKa values differ by 2 pH units or less. The PrideauxWard mixture comprises phosphate, phenyl acetate, and borate plus HCl and covers the range from 2 to 12 pH units. The McIlvaine buffer is a mixture of citric acid and Na2HPO4 that covers the range from pH 2.2 to 8.0. The Britton-Robinson system consists of acetic acid, phosphoric acid, and boric acid plus NaOH and covers the range from pH 4.0 to 11.5. A mixture composed of Na2CO3 , NaH2PO4 , citric acid, and 2-amino-2-methyl-1,3-propanediol covers the range from pH 2.2 to 11.0. General directions for the preparation of buffer solutions of varying pH but fixed ionic strength are given by Bates.* Preparation of McIlvaine buffered solutions at ionic strengths of 0.5 and 1.0 and Britton-Robinson solutions of constant ionic strength have been described by Elving et al.† and Frugoni,‡ respectively.

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* Bates, Determination of pH, Theory and Practice, Wiley, New York, 1964, pp. 121–122. † Elving, Markowitz, and Rosenthal, Anal. Chem., 28:1179 (1956). ‡ Frugoni, Gazz. Chim. Ital., 87:L403 (1957).

8.4

REFERENCE ELECTRODES

TABLE 8.20 Potentials of Reference Electrodes in Volts as a Function of Temperature Liquid-junction potential included. Temp., ⬚C

0.1M KCl Calomel*

1.0M KCl Calomel*

0 5 10 15

0.3367

0.2883

0.3362 0.3361

0.2868

0.2556

20 25 30 35

0.3358 0.3356 0.3354 0.3351

0.2844 0.2830 0.2815

38 40 45 50

0.3350 0.3345

0.2782

0.3315

0.2745

0.22737

0.3248

0.2702

0.2235

55 60 70 80 90

3.5M KCl Calomel*

Satd. KCl Calomel*

1.0M KCl Ag/AgCl†

1.0M KBr Ag/AgBr‡

1.0M KI Ag/AgI§

0.25918 0.25387 0.2511

0.23655 0.23413 0.23142 0.22857

0.08128 0.07961 0.07773 0.07572

⫺0.14637 ⫺0.14719 ⫺0.14822 ⫺0.14942

0.2520 0.2501 0.2481

0.24775 0.24453 0.24118 0.2376

0.22557 0.22234 0.21904 0.21565

0.07349 0.07106 0.06856 0.06585

⫺0.15081 ⫺0.15244 ⫺0.15405 ⫺0.15590

0.2448 0.2439

0.2355 0.23449

0.21208 0.20835 0.20449

0.06310 0.06012 0.05704

⫺0.15788 ⫺0.15998 ⫺0.16219

0.20056 0.19649 0.18782 0.1787 0.1695

0.0251

0.2083

* Bates et al., J. Research Natl. Bur. Standards, 45, 418 (1950). † Bates and Bower, J. Research Natl. Bur. Standards, 53, 283 (1954). ‡ Hetzer, Robinson and Bates, J. Phys. Chem., 66, 1423 (1962). § Hetzer, Robinson and Bates, J. Phys. Chem., 68, 1929 (1964).

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TABLE 8.20 Potentials of Reference Electrodes in Volts as a Function of Temperature (Continued) Temp., ⬚C

125

150

175

200

1.0M KCl Ag/AgCl*

0.1330

0.1032

0.0708

0.0348

1.0M KBr Ag/AgBr†

⫺0.0048

⫺0.0312

⫺0.0612

⫺0.0951

225

250

275

⫺0.0051

⫺0.054

⫺0.090

* Greeley et al., J. Phys. Chem., 64, 652 (1960). † Towns et al., J. Phys. Chem., 64, 1861 (1960).

The values of several additional reference electrodes at 25⬚C are listed: Ag/AgCl, satd. KCl

0.198

Ag/AgCl, 01M KCl

0.288

Hg/HgO, 1.0M NaOH

0.140

Hg/HgO, 0.1M NaOH

0.165

Hg/Hg2SO4 , satd. K2SO4 (22⬚C)

0.658

Hg/Hg2SO4 , satd. KCl

0.655

TABLE 8.21 Potentials of Reference Electrodes (in Volts) at 25⬚C for Water– Organic Solvent Mixtures Electrolyte solution of 1M HCl.

Solvent, wt % 5 10 20 30 40 45 50 60 70 80 82 90 94.2 98 99 100

Methanol, Ag/AgCl

Ethanol, Ag/AgCl

0.2153 0.2090

0.2146 0.2075 0.2003 0.1945

0.1968

2-Propanol, Ag/AgCl 0.2180 0.2138 0.2063

Acetone, Ag/AgCl 0.2190 0.2156 0.2079

Dioxane, Ag/AgCl

0.2031

0.1859

Ethylene glycol, Ag/AgCl 0.2190 0.2160 0.2101 0.2036 0.1972

Methanol, calomel

0.255

0.1818 0.1492 0.1135 0.0841

0.096

0.2501

0.243

0.1635 0.1859 0.173 0.158 0.136

Dioxane, calomel

0.2104

0.158 0.1807 0.0659 ⫺0.034

0.216

⫺0.0614

0.1126 ⫺0.0014

0.0215 0.103 ⫺0.0099

⫺0.0081

⫺0.53

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Electrometric Measurement of pH

The pH value is defined for an aqueous solution in an operational (arbitrary but reproducible) manner according to the Bates-Guggenheim convention: pHx ⫽ pHs ⫹

Ex ⫺ Es 2.3026RT/F

where R is the gas constant per mole, T is the temperature on the absolute scale, and F is the faraday. The pHx of the unknown medium is calculated from that of an accepted standard (pHs ) and the measured difference in the emf (E) of the electrode combination when the standard solution is removed from the cell and replaced by the unknown. The double vertical line marks a liquid junction. Electrodes as fabricated exhibit variations in the reproducibility of the reference electrode, in the liquid-junction potential, and, with glass electrodes, in the asymmetry potential. These differences are all eliminated in the standardizing procedure with standard reference pH buffers. (See R. G. Bates, Determination of pH, Theory and Practice, Wiley, New York, 1964.) Electrode reversible to hydrogen ions

冨

Standard reference buffer or unknown solution

冩

Salt bridge (KCl. 3.5M or saturated)

冨

Reference electrode

An electrometric pH-measurement system consists of (1) pH-responsive electrode, (2) reference electrode, and (3) potential-measuring device— some form of high-impedance electronic voltmeter for glass-electrode combinations and this or a potentiometer arrangement for other pH-responsive electrodes. Electronic pH meters are simply voltmeters with scale divisions in pH units which are equivalent to the values of 2.3026RT/F (in mV) per pH unit. Values of this function at several temperatures are given in Table 8.22. There is no compensation incorporated in the meter for the changes in pH of the test solution as a function of temperature. Reliability of an indicator–reference electrode combination must be ascertained by standardization of the pH meter with one standard buffer and checking the pH response by immersing the combination in a second and different reference buffer. The temperature compensator on a pH meter varies the instrument definition of a pH unit from 54.20 mV at 0⬚C to perhaps 66.10 mV at 60⬚C. This permits one to measure the pH of the sample (and reference buffer standard) at its actual temperature and thus avoid error due to dissociation equilibria and to junction potentials which have significant temperature coefficients.

TABLE 8.22 Values of 2.3026RT/F at Several Temperatures In millivolts. t ⬚C

Value

t ⬚C

Value

t ⬚C

Value

t ⬚C

Value

0 5 10 15 18 20

54.197 55.189 56.181 57.173 57.767 58.165

25 30 35 38 40 45

59.157 60.149 61.141 61.737 62.133 63.126

50 55 60 65 70 75

64.118 65.110 66.102 67.094 68.086 69.078

80 85 90 95 100

70.070 71.062 72.054 73.046 74.038

Report of the National Academy of Sciences: National Research Council Committee of Fundamental Constants, 1963.

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INDICATORS

TABLE 8.23 Indicators for Aqueous Acid-Base Titrations This table lists some selected indicators. The pH range or transition interval given in the third column may vary appreciably from one observer to another, and, in addition, it is affected by ionic strength, temperature, and illumination; consequently only approximate values can be given. They should be considered to refer to solutions having low ionic strengths and a temperature of about 25⬚C. In the fourth column the pKa (⫺log Ka) of the indicator as determined spectrophotometrically is listed. In the fifth column the wavelength of maximum absorption is given first for the acidic and then for the basic form of the indicator, and the same order is followed in giving the colors in the sixth column. The abbreviations used to describe the colors of the two forms of the indicator are as follows: B, blue V, violet Y, yellow O, orange C, colorless

Indicator Cresol red (acid range) Cresol purple (acid range) Thymol blue (acid range) Tropeolin OO 2,6-Dinitrophenol 2,4-Dinitrophenol Methyl yellow Methyl orange Bromophenol blue Bromocresol green Methyl red Chlorophenol red Bromocresol purple Bromophenol red p-Nitrophenol Bromothymol blue Neutral red Phenol red m-Nitrophenol

Chemical name

G, green P, purple R, red O-Br, orange-brown

pH range

pKa

␭max , nm

Color change

o-Cresolsulfonephthalein

0.2– 1.8

R-Y

m-Cresolsulfonephthalein

1.2– 2.8

1.51

533, —

R-Y

Thymolsulfonephthalein

1.2– 2.8

1.65

544, 430

R-Y

Diphenylamino-p-benzene sodium sulfonate 2,6-Dinitrophenol 2,4-Dinitrophenol Dimethylaminoazobenzene Dimethylaminoazobenzene sodium sulfonate Tetrabromophenolsulfonephthalein Tetrabromo-m-cresolsulfonephthalein o-Carboxybenzeneazodimethylaniline Dichlorophenolsulfonephthalein Dibromo-o-cresolsulfonephthalein Dibromophenolsulfonephthalein p-Nitrophenol Dibromothymolsulfonephthalein Aminodimethylaminotoluphenazonium chloride Phenolsulfonephthalein m-Nitrophenol

1.3– 3.2

2.0

527, —

R-Y

2.4– 4.0 2.5– 4.3 2.9– 4.0 3.1– 4.4

3.69 3.90 3.3 3.40

508, — 522, 464

C-Y C-Y R-Y R-O

3.0– 4.6

3.85

436, 592

Y-BV

4.0– 5.6

4.68

444, 617

Y-B

4.4– 6.2

4.95

530, 427

R-Y

5.4– 6.8

6.0

— , 573

Y-R

5.2– 6.8

6.3

433, 591

Y-P

— , 574

Y-R

320, 405 433, 617

C-Y Y-B

5.2– 6.8 5.3– 7.6 6.2– 7.6

7.15 7.1

6.8– 8.0

7.4

6.4– 8.0 6.4– 8.8

7.9 8.3

R-Y 433, 558 — , 570

Y-R C-Y

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TABLE 8.23 Indicators for Aqueous Acid-Base Titrations (Continued)

Indicator

Chemical name

Cresol red m-Cresol purple Thymol blue Phenolphthalein ␣-Naphtholbenzein Thymolphthalein Alizarin Yellow R

o-Cresolsulfonephthalein m-Cresolsulfonephthalein Thymolsulfonephthalein Phenolphthalein ␣-Naphtholbenzein Thymolphthalein 5-(p-Nitrophenylazo)salicyclic acid, Na salt p-Sulfobenzenazoresorcinol 2,4,6-Trinitrophenylmethylnitroamine

Tropeolin O Nitramine

pH range 7.2– 8.8 7.6– 9.2 8.0– 9.6 8.0– 10.0 9.0– 11.0 9.4– 10.6 10.0– 12.0

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pKa

␭max , nm

8.2 8.32 8.9 9.4

434, 572 — , 580 430, 596 — , 553

10.0 11.16

— , 598

Color change Y-R Y-P Y-B C-R Y-B C-B Y-V

11.0– 13.0

Y-O-Br

10.8– 13.0

C-O-Br

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TABLE 8.24 Mixed Indicators Mixed indicators give sharp color changes and are especially useful in titrating to a given titration exponent (pI). The information given in this table is from the two-volume work Volumetric Analysis by Kolthoff and Stenger, published by Interscience Publishers, Inc., New York, 1942 and 1947, and reproduced with their permission.

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Color Composition of Indicator Solution

pI

1 part 0.1% methyl yellow in alc. 1 part 0.1% methylene blue in alc.

*

1 part 0.14% xylene cyanol FF in alc. 1 part 0.1% methyl orange in aq.

*

1 part 0.1% methyl orange in aq. 1 part 0.25% indigo carmine in aq.

*

Notes

Blue-violet

Green

Still green at pH 3.4, blue-violet at 3.2†

3.8

Violet

Green

Color is gray at pH 3.8

4.1

Violet

Green

Good indicator, especially in artificial light

4.3

Violet

Green

Orange

Blue-green

Yellow at pH 3.5, greenish yellow at 4.0, weakly green at 4.3

Wine-red

Green

Very sharp color change†

Red-violet

Green

Color is red-violet at pH 5.2, a dirty blue at 5.4, and a dirty green at 5.6

Green

Violet

Pale violet at pH 5.8

Yellow-green

Blue-violet

Blue-green at pH 5.4, blue at 5.8, blue with a touch of violet at 6.0, blue-violet at 6.2

Yellow

Violet-blue

Yellow-violet at pH 6.2, violet at 6.6, blue-violet at 6.8

Violet

Blue

4.3

3 parts 0.1% bromcresol green in alc. 1 part 0.2% methyl red in alc.

5.1 * 5.4 5.8 6.1

1 part 0.1% bromcresol purple sodium salt in aq. 1 part 0.1% bromthymol blue sodium salt in aq.

6.7

2 parts 0.1% bromthymol blue sodium salt in aq. 1 part 0.1% azolitmin in aq.

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1 part 0.1% bromcresol green sodium salt in aq. 1 part 0.1% chlorphenol red sodium salt in aq.

LEFT

1 part 0.1% bromcresol green sodium salt in aq. 1 part 0.02% methyl orange in aq.

1 part 0.1% chlorphenol red sodium salt in aq. 1 part 0.1% aniline blue in water

Alkaline

3.25

1 part 0.1% methyl orange in aq. 1 part 0.1% aniline blue in aq.

1 part 0.2% methyl red in alc. 1 part 0.1% methylene blue in alc.

Acid

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*

Green

Violet blue at pH 7.0†

Rose

Green

Dirty green at pH 7.4, pale rose at 7.2, clear rose at 7.0

Yellow

Violet

Orange at pH 7.2, beautiful violet at 7.4, color fades on standing

Yellow

Violet

Dirty green at pH 7.2, pale violet at 7.4, strong violet at 7.6†

Yellow

Violet

Rose at pH 8.2, distinctly violet at 8.4†

Pale rose

Violet

Pale violet at pH 8.2, strong violet at 8.4

Pale rose

Violet

Pale green at pH 8.6, violet at 9.0

Green

Violet

Pale blue at pH 8.8, violet at 9.0

Yellow

Violet

From yellow thru green to violet†

Colorless

Violet

Rose at pH 9.6, violet at 10; sharp color change

7.0 7.2

2 parts 0.1% cyanine in 50% alc. 1 part 0.1% phenol red in 50% alc.

7.3

1 part 0.1% bromthymol blue sodium salt in aq. 1 part 0.1% phenol red sodium salt in aq.

7.5

1 part 0.1% cresol red sodium salt in aq. 3 parts 0.1% thymol blue sodium salt in aq.

8.3

2 parts 0.1% ␣-naphtholphthalein in alc. 1 part 0.1% cresol red in alc.

8.3

1 part 0.1% ␣-naphtholphthalein in alc. 3 parts 0.1% phenolphthalein in alc.

8.9 * 8.9 9.0

1 part 0.1% phenolphthalein in alc. 1 part 0.1% thymolphthalein in alc.

9.9

1 part 0.1% phenolphthalein in alc. 2 parts 0.2% Nile blue in alc.

10.0

Blue

Red

Violet at pH 10†

2 parts 0.1% thymolphthalein in alc. 1 part 0.1% alizarin yellow in alc.

10.2

Yellow

Violet

Sharp color change

2 parts 0.2% Nile blue in aq. 1 part 0.1% alizarin yellow in alc.

Green

Red-brown

10.8

RIGHT

1 part 0.1% thymol blue in 50% alc. 3 parts 0.1% phenolphthalein in 50% alc.

INTERACTIVE

* Keep in a dark bottle.

(McGHP)

1 part 0.1% neutral red in alc. 1 part 0.1% bromthymol blue in alc.

1 part 0.1% phenolphthalein in alc. 2 parts 0.1% methyl green in alc.

Violet-blue

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1 part 0.1% neutral red in alc. 1 part 0.1% methylene blue in alc.

† Excellent indicator.

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TABLE 8.25 Fluorescent Indicators

Name Benzoflavine 3,6-Dihydroxyphthalimide Eosin (tetrabromofluorescein) 4-Ethoxyacridone 3,6-Tetramethyldiaminoxanthone Esculin Anthranilic acid

3-Amino-1-naphthoic acid

1-Naphthylamino-6-sulfonamide (also the 1-, 7-) 2-Naphthylamino-6-sulfonamide (also the 2-, 8-) 1-Naphthylamino-5-sulfonamide 1-Naphthoic acid Salicylic acid Phloxin BA extra (tetrachlorotetrabromofluorescein) Erythrosin B (tetraiodofluorescein) 2-Naphthylamine Magdala red p-Aminophenylbenzenesulfonamide 2-Hydroxy-3-naphthoic acid Chromotropic acid 1-Naphthionic acid 1-Naphthylamine 5-Aminosalicylic acid Quinine o-Methoxybenzaldehyde o-Phenylenediamine p-Phenylenediamine Morin (2⬘,4⬘,3,5,7-pentahydroxyflavone) Thioflavine S Fluorescein Dichlorofluorescein ␤-Methylesculetin Quininic acid ␤-Naphthoquinoline Resorufin (7-oxyphenoxazone)

pH Range

Color Change Acid to Base

⫺0.3 to 1.7 0 to 2.4 6.0 to 8.0 0 to 3.0 1.2 to 3.2 1.2 to 3.4 1.5 to 2.0 1.5 to 3.0 4.5 to 6.0 12.5 to 14 1.5 to 3.0 4.0 to 6.0 11.6 to 13.0 1.9 to 3.9 9.6 to 13.0 1.9 to 3.9 9.6 to 13.0 2.0 to 4.0 9.5 to 13.0 2.5 to 3.5 2.5 to 4.0 2.5 to 4.0

Yellow to green Blue to green Green to yellow/green Non-fl to green Green to blue Green to blue Weak blue to strong blue Non-fl to light blue Light blue to dark blue Dark blue to non-fl Non-fl to green Green to blue Blue to non-fl Non-fl to green Green to non-fl Non-fl to dark blue Dark blue to non-fl Non-fl to yellow/orange Yellow/orange to non-fl Non-fl to blue Non-fl to dark blue Non-fl to dark blue

2.5 to 4.0 2.8 to 4.4 3.0 to 4.0 3.0 to 4.0 3.0 to 6.8 3.1 to 4.4 3 to 4 10 to 12 3.4 to 4.8 3.1 to 4.4 3.0 to 5.0 9.5 to 10.0 3.1 to 4.4 3.1 to 4.4 3.1 to 4.4 3.1 to 4.4 8 to 9.8 3.1 to 4.4 4.0 to 4.5 4.0 to 6.6 4.0 to 6.2 9.0 to 10.0 4.0 to 5.0 4.4 to 6.3 4.4 to 6.4

Non-fl to light green Non-fl to violet Non-fl to purple Non-fl to light blue Blue to green Non-fl to light blue Non-fl to blue Blue to yellow-green Non-fl to blue Non-fl to light green Blue to weak violet Weak violet to non-fl Non-fl to green Green to non-fl Non-fl to orange/yellow Non-fl to green Green to yellow/green Dark blue to light blue Pink/green to green Blue green to green Non-fl to blue Blue to light green Yellow to blue Blue to non-fl Yellow to orange

Indicator Solution 1 1 4, 1% 1 1 2 (50% ethanol)

2 (as sulfate in 50% ethanol) 3 3 3 4 4 (0.5%) 2 4 (0.2%) 1 3 4 (0.1%) 4 (5%) 4 1 1 (0.2% fresh) 1 (0.1%) 4 (0.2%) 5 5 6 (0.2%) 6 (0.2%) 4 (1%) 1 1 6 (satd) 3

Indicator solutions: 1, 1% solution in ethanol; 2, 0.1% solution in ethanol; 3, 0.05% solution in 90% ethanol; 4, sodium or potassium salt in distilled water; 5, 0.2% solution in 70% ethanol; 6, distilled water. Reference: G.F. Kirkbright, “Fluorescent Indicators,” Chap. 9 in Indicators, E. Bishop (ed.), Pergamon Press, Oxford, 1972.

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TABLE 8.25 Fluorescent Indicators (Continued)

Name Acridine 3,6-Dihydroxyxanthone 5,7-Dihydroxy-4-methylcoumarin 3,6-Dihydroxyphthalic acid dinitrile 1,4-Dihydroxybenzenedisulfonic acid Luminol 2-Naphthol-6-sulfonic acid Quinoline 1-Naphthol-5-sulfonic acid Umbelliferone Magnesium-8-hydroxyquinolinate

pH Range

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Color Change Acid to Base

5.2 to 6.6 5.4 to 7.6 5.5 to 5.8 5.8 to 8.2 6 to 7 6 to 7 5– 7 to 8– 9 6.2 to 7.2 6.5 to 7.5 6.5 to 8.0 6.5 to 7.5

Green to violet Non-fl to blue/violet Light blue to dark blue Blue to green Non-fl to light blue Non-fl to blue Non-fl to blue Blue to non-fl Non-fl to green Non-fl to blue Non-fl to yellow

Orcinaurine Diazo brilliant yellow Coumaric acid ␤-Methylumbelliferone Harmine 2-Naphthol-6,8-disulfonic acid Salicylaldehyde semicarbazone 1-Naphthol-2-sulfonic acid Salicylaldehyde acetylhydrazone Salicylaldehyde thiosemicarbazone 1-Naphthol-4-sulfonic acid Naphthol AS 2-Naphthol Acridine orange Orcinsulfonephthalein 2-Naphthol-3,6-disulfonic acid Ethoxyphenylnaphthostilbazonium chloride o-Hydroxyphenylbenzothiazole o-Hydroxyphenylbenzoxazole o-Hydroxyphenylbenzimidazole Coumarin 6,7-Dimethoxyisoquinoline-1-carboxylic acid

6.5 to 8.0 6.5 to 7.5 7.2 to 9.0 ⬎7.0 7.2 to 8.9 7.5 to 9.1 7.6 to 8.0 8.0 to 9.0 8.3 8.4 8.2 8.2 to 10.3 8.5 to 9.5 8.4 to 10.4 8.6 to 10.0 9.0 to 9.5 9 to 11 9.3 9.3 9.9 9.5 to 10.5 9.5 to 11.0

Non-fl to green Non-fl to blue Non-fl to green Non-fl to blue Blue to yellow Blue to light blue Yellow to blue Dark blue to light blue Non-fl to green/blue Non-fl to blue/green Dark blue to light blue Non-fl to yellow/green Non-fl to blue Non-fl to yellow/green Non-fl to yellow Dark blue to light blue Green to non-fl Non-fl to blue green Non-fl to blue/violet Non-fl to blue/violet Non-fl to light green Yellow to blue

1-Naphthylamino-4-sulfonamide

9.5 to 13.0

Dark blue to white/blue

Indicator Solution 2 1 1 4 (0.1%) 4 6 (satd) 6 (satd) 6 (0.1% in 0.01 M HCl) 6 (0.03%) 1 2 (0.3%) 4 2 4 2 2 4 4 2 1 4 1 2 2 2 0.1% in glycerine/ ethanol/water in 2 : 2 : 18 ratio 3

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TABLE 8.26 Selected List of Oxidation-Reduction Indicators

Name Bis(5-bromo-1,10-phenanthroline) ruthenium(II) dinitrate Tris(5-nitro-1,10-phenanthroline) iron(II) sulfate Iron(II)-2,2⬘,2⬙-tripyridine sulfate Tris(4,7-diphenyl-1,10-phenanthroline) iron(II) disulfate o,m⬘-Diphenylaminedicarboxylic acid Setopaline p-Nitrodiphenylamine Tris(1,10-phenanthroline)-iron(II) sulfate

pH ⫽ 7

Suitable pH Range

Color Change Upon Oxidation

1.41*

Red to faint blue

1.25*

Red to faint blue

1.25* 1.13 (4.6 M H2SO4 )* 0.87 (1.0 M H2SO4 )* 1.12 1.06 (trans)† 1.06 1.06 (1.00 M H2SO4 )* 1.00 (3.0 M H2SO4 )* 0.89 (6.0 M H2SO4 )* 1.01 (trans)† 1.00 (trans)† 1.00 (trans)† 0.99 (trans)† 0.97*

Pink to faint blue Red to faint blue

Yellow-green to yellow-red Yellow-green to pink Green-yellow to bluish red Green-yellow to orange Red to faint blue

0.94

Colorless to pink

0.92 0.87 0.859 (0.1 M H2SO4 )

Colorless to blue Colorless to blue Green to pink

0.85

Colorless to violet

Colorless to blue-violet Yellow to orange Colorless to violet Red to faint blue

LEFT INTERACTIVE

Setoglaucine O Xylene cyanole FF Erioglaucine A Eriogreen Tris(2,2⬘-bipyridine)-iron(II) hydrochloride 2-Carboxydiphenylamine [N-phenylanthranilic acid] Benzidine dihydrochloride o-Toluidine Bis(1,10-phenanthroline)-osmium(II) perchlorate Diphenylamine-4-sulfonate (Na salt)

pH ⫽ 0

(McGHP)

Reduction Potential (30⬚C) in Volts at

8.122

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Colorless to red

0.81 0.76 0.76 0.76 0.76 0.712‡ 0.70 0.680‡ 0.668‡ 0.668‡ 0.583

Yellow to violet Red to pale yellow Colorless to violet Colorless to violet Colorless to red Colorless to blue Colorless to red

0.59 0.563‡ 0.54

0.310

1.5– 6.3

0.224 0.217 0.216 0.047

2– 9.5 6.3– 11.4 7.0– 12.3 0– 11

0.064

1– 13

Colorless to blue Colorless to blue Colorless to blue Red to faint blue Colorless to violet Colorless to blue Colorless to violet-blue Colorless to blue Colorless to blue

1– 13 1.4– 12.3

0.365‡

⫺0.046

⬍9

Colorless to blue

0.332‡ 0.291‡ 0.280‡ 0.262‡ 0.24‡ 0.155 0.047‡

⫺0.081 ⫺0.125 ⫺0.252 ⫺0.157 ⫺0.289

⬍9 ⬍9 1– 11 ⬍9 1– 12 6– 10 3– 8.6 2– 11

Colorless to blue Colorless to blue Colorless to violet-blue Colorless to blue Colorless to violet-blue Red to colorless Colorless to red Colorless to red-violet

INTERACTIVE

0.021 0.011 ⫺0.119

RIGHT

0.532‡ 0.406‡

⫺0.299 ⫺0.323

(McGHP)

0.85

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3,3⬘-Dimethoxybenzidine dihydrochloride [o-dianisidine] Ferrocyphen 4⬘-Ethoxy-2,4-diaminoazobenzene N,N-Diphenylbenzidine Diphenylamine N,N-Dimethyl-p-phenylenediamine Variamine blue B hydrochloride N-Phenyl-1,2,4-benzenetriamine Bindschedler’s green 2,6-Dichloroindophenol (Na salt) 2,6-Dibromophenolindophenol Brilliant cresyl blue [3-amino-9-dimethylamino-10-methylphenoxyazine chloride] Iron(II)-tetrapyridine chloride Thionine [Lauth’s violet] Starch (soluble potato, I⫺3 present) Gallocyanine (25⬚C) Methylene blue Nile blue A [aminonaphthodiethylaminophenoxazine sulfate] Indigo-5,5⬘,7,7⬘-tetrasulfonic acid (Na salt) Indigo-5,5⬘,7-trisulfonic acid (Na salt) Indigo-5,5⬘-disulfonic acid (Na salt) Phenosafranine Indigo-5-monosulfonic acid (Na salt) Safranine T Bis(dimethylglyoximato)-iron(II) chloride Induline scarlet Neutral red

* Transition point is at higher potential than the tabulated formal potential because the molar absorptivity of the reduced form is very much greater than that of the oxidized form. † Trans ⫽ first noticeable color transition; often 60 mV less than E⬚ ‡ Values of E⬚ are obtained by extrapolation from measurements in weakly acid or weakly alkaline systems.

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SECTION 8

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ELECTRODE POTENTIALS

TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C Standard potentials are tabulated except when a solution composition is stated; the latter are formal potentials and the concentrations are in mol/liter.

Half-reaction

Standard or formal potential

Actinium Ac3⫹ ⫹ 3e⫺ ⫽ Ac

⫺2.13

Aluminum Al3⫹ ⫹ 3e⫺ ⫽ Al AlF 36⫺ ⫹ 3e⫺ ⫽ Al ⫹ 6F⫺ Al(OH)⫺4 ⫹ 3e⫺ ⫽ Al ⫹ 4OH⫺

⫺1.676 ⫺2.07 ⫺2.310

Americium AmO22⫹ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Am4⫹ ⫹ 2H2O AmO22⫹ ⫹ e⫺ ⫽ AmO2⫹ AmO⫹2 ⫹ 4H⫹ ⫹ e⫺ ⫽ Am4⫹ ⫹ 2H2O AmO⫹2 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Am3⫹ ⫹ 2H2O Am4⫹ ⫹ e⫺ ⫽ Am3⫹ Am4⫹ ⫹ 4e⫺ ⫽ Am Am3⫹ ⫹ 3e⫺ ⫽ Am

1.20 1.59 0.82 1.72 2.62 ⫺0.90 ⫺2.07

Antimony Sb(OH)⫺4 ⫹ 2e⫺ ⫽ SbO2⫺ ⫹ 2OH⫺ ⫹ 2H2O SbO⫺2 ⫹ 2H2O ⫹ 3e⫺ ⫽ Sb ⫹ 4OH⫺ Sb ⫹ 3H2O ⫹ 3e⫺ ⫽ SbH3 ⫹ 3OH⫺ Sb2O5 ⫹ 6H⫹ ⫹ 4e⫺ ⫽ 2SbO⫹ ⫹ 3H2O Sb2O5 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Sb2O3 ⫹ 2H2O Sb2O5 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ Sb2O4 ⫹ H2O Sb2O4 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ Sb2O3 ⫹ H2 SbO⫹ ⫹ 2H⫹ ⫹ 3e⫺ ⫽ Sb ⫹ H2O Sb ⫹ 3H⫹ ⫹ 3e⫺ ⫽ SbH3

⫺0.465 0.639 ⫺1.338 0.605 0.699 1.055 0.342 0.204 ⫺0.510

Arsenic H3AsO4 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ HAsO2 ⫹ 2H2O HAsO2 ⫹ 3H⫹ ⫹ 3e⫺ ⫽ As ⫹ 2H2O As ⫹ 3H⫹ ⫹ 3e⫺ ⫽ AsH3 AsO34⫺ ⫹ 2H⫹ ⫹ 2e⫺ ⫽ AsO2⫺ ⫹ 4OH⫺ AsO⫺2 ⫹ 2H2O ⫹ 3e⫺ ⫽ As ⫹ 4OH⫺ As ⫹ 3H2O ⫹ 3e⫺ ⫽ AsH3 ⫹ 3OH⫺

0.560 0.240 ⫺0.225 ⫺0.67 ⫺0.68 ⫺1.37

Astatine HAtO3 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ HAtO ⫹ 2H2 2HAtO ⫹ 2H⫹ ⫹ 2e⫺ ⫽ At2 ⫹ 2H2O At2 ⫹ 2e⫺ ⫽ 2At⫺ Barium BaO2 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Ba2⫹ ⫹ 2H2O Ba2⫹ ⫹ 2e⫺ ⫽ Ba

Solution composition

1 NaOH 1 NaOH 1 NaOH

ca. 1.4 ca. 0.7 0.20 2.365 ⫺2.92

Source: A. J. Bard, R. Parsons, and J. Jordan (eds.), Standard Potentials in Aqueous Solution (prepared under the auspices of the International Union of Pure and Applied Chemistry), Marcel Dekker, New York, 1985; G. Charlot et al., Selected Constants: Oxidation-Reduction Potentials of Inorganic Substances in Aqueous Solution, Butterworths, London, 1971.

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TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction

Standard or formal potential

Berkelium Bk 4⫹ ⫹ 4e⫺ ⫽ Bk Bk 4⫹ ⫹ e⫺ ⫽ Bk3⫹ Bk 3⫹ ⫹ 3e⫺ ⫽ Bk

⫺1.05 1.67 ⫺2.01

Beryllium Be 2⫹ ⫹ 2e ⫺ ⫽ Be

⫺1.99

Bismuth Bi 2O4 (bismuthate) ⫹ 4H⫹ ⫹ 2e⫺ ⫽ 2BiO⫹ ⫹ 2H2O Bi 3⫹ ⫹ 3e ⫺ ⫽ Bi Bi ⫹ 3H⫹ ⫹ 3e ⫺ ⫽ BiH3 BiCl⫺4 ⫹ 3e ⫺ ⫽ Bi ⫹ 4Cl ⫺ BiBr ⫺4 ⫹ 3e ⫺ ⫽ Bi ⫹ 4Br ⫺ BiOCl ⫹ 2H⫹ ⫹ 3e ⫺ ⫽ Bi ⫹ H2O ⫹ Cl ⫺

1.59 0.317 ⫺0.97 0.199 0.168 0.170

Boron B(OH)3 ⫹ 3H⫹ ⫹ 3e ⫺ ⫽ B ⫹ 3H2O BO⫺2 ⫹ 6H2O ⫹ 8e ⫺ ⫽ BH 3⫺ ⫹ 8OH ⫺ B(OH)⫺4 ⫹ 3e ⫺ ⫽ B ⫹ 4OH⫺

⫺0.890 ⫺1.241 ⫺1.811

Bromine BrO⫺4 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ BrO3⫺ ⫹ H2O BrO⫺3 ⫹ 6H⫹ ⫹ 6e ⫺ ⫽ Br ⫺ ⫹ 3H2O BrO⫺3 ⫹ 5H⫹ ⫹ 4e ⫺ ⫽ HBrO ⫹ 2H2O 2BrO⫺3 ⫹ 12H⫹ ⫹ 10e ⫺ ⫽ Br2 ⫹ 6H2O 2HBrO ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ Br2 ⫹ 2H2O HBrO ⫹ H⫹ ⫹ 2e ⫺ ⫽ Br ⫺ ⫹ H2O BrO⫺ ⫹ H2O ⫹ 2e ⫺ ⫽ Br ⫺ ⫹ 2OH ⫺ Br ⫺3 ⫹ 2e ⫺ ⫽ 3Br ⫺ Br2(aq) ⫹ 2e ⫺ ⫽ 2Br ⫺

1.853 1.478 1.444 1.5 1.604 1.341 0.76 1.050 1.087

Cadmium Cd 2⫹ ⫹ 2e ⫺ ⫽ Cd Cd 2⫹ ⫹ Hg ⫹ 2e ⫺ ⫽ Cd(Hg) CdCl 24⫺ ⫹ 2e ⫺ ⫽ Cd ⫹ 4Cl ⫺ Cd(CN)24⫺ ⫹ 2e ⫺ ⫽ Cd ⫹ 4CN⫺ Cd(NH3)42⫹ ⫹ 2e ⫺ ⫽ Cd ⫹ 4NH3 Cd(OH)24⫺ ⫹ 2e ⫺ ⫽ Cd ⫹ 4OH ⫺

⫺0.403 ⫺0.352 ⫺0.453 ⫺0.943 ⫺0.622 ⫺0.670

Calcium CaO2 ⫹ 4H⫹ ⫹ 2e ⫺ ⫽ Ca2⫹ ⫹ H2O Ca2⫹ ⫹ 2e ⫺ ⫽ Ca Ca ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ CaH2

2.224 ⫺2.84 0.776

Californium Cf 3⫹ ⫹ 3e ⫺ ⫽ Cf Cf 3⫹ ⫹ e ⫺ ⫽ Cf 2⫹ Cf 2⫹ ⫹ 2e ⫺ ⫽ Cf

⫺1.93 ⫺1.6 ⫺2.1

Carbon CO2 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ CO ⫹ H2O CO2 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ HCOOH 2CO2 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ H2C2O4 C2O24⫺ ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ 2HCOO⫺ HCOOH ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ HCHO ⫹ H2O

⫺0.106 ⫺0.20 ⫺0.481 0.145 0.034

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Solution composition

1 NaOH

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TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction C2N2 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ 2HCN HCNO ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ CO ⫹ H2O HCHO ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ CH3OH CNO⫺ ⫹ H2O ⫹ 2e ⫺ ⫽ CN⫺ ⫹ 2OH⫺ Cerium Ce(IV) ⫹ e ⫺ ⫽ Ce(III)

Ce3⫹ ⫹ 3e ⫺ ⫽ Ce Cesium Cs⫹ ⫹ e ⫺ ⫽ Cs Cs⫹ ⫹ Hg ⫹ e ⫺ ⫽ Cs(Hg) Chlorine ClO⫺4 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ ClO3⫺ ⫹ H2O 2ClO⫺4 ⫹ 16H⫹ ⫹ 14e ⫺ ⫽ Cl2 ⫹ 8H2O ClO⫺4 ⫹ 8H⫹ ⫹ 8e ⫺ ⫽ Cl⫺ ⫹ 4H2O ClO⫺3 ⫹ 2H⫹ ⫹ e ⫺ ⫽ ClO2(g) ⫹ H2O ClO⫺3 ⫹ 3H⫹ ⫹ 2e ⫺ ⫽ HClO2 ⫹ H2O 2ClO⫺3 ⫹ 12H⫹ ⫹ 10e ⫺ ⫽ Cl2 ⫹ 6H2O ClO⫺3 ⫹ 6H⫹ ⫹ 6e ⫺ ⫽ Cl ⫺ ⫹ 3H2O ClO2(g) ⫹ H⫹ ⫹ e ⫺ ⫽ HClO2 HClO2 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ HClO ⫹ H2O HClO2 ⫹ 3H⫹ ⫹ 4e ⫺ ⫽ Cl⫺ ⫹ 2H2O 2HClO2 ⫹ 6H⫹ ⫹ 6e ⫺ ⫽ Cl2(g) ⫹ 4H2O 2ClO⫺ ⫹ 2H2O ⫹ 2e ⫺ ⫽ Cl2(g) ⫹ 4OH⫺ ClO⫺ ⫹ H2O ⫹ 2e ⫺ ⫽ Cl⫺ ⫹ 2OH⫺ Cl⫺3 ⫹ 2e ⫺ ⫽ 3Cl⫺ Cl2(aq) ⫹ 2e ⫺ ⫽ 2Cl⫺ Chromium Cr2O27⫺ ⫹ 14H⫹ ⫹ 6e ⫺ ⫽ 2Cr 3⫹ ⫹ 7H2O CrO24⫺ ⫹ 4H2O ⫹ 3e ⫺ ⫽ Cr(OH)4⫺ ⫹ 4OH⫺ Cr 3⫹ ⫹ e ⫺ ⫽ Cr 2⫹ Cr 3⫹ ⫹ 3e ⫺ ⫽ Cr Cr 2⫹ ⫹ 2e ⫺ ⫽ Cr Cobalt CoO2 ⫹ 4H⫹ ⫹ e ⫺ ⫽ Co3⫹ ⫹ 2H2O Co(H2O)36⫹ ⫹ e ⫺ ⫽ Co(H2O)62⫹ Co(NH3)36⫹ ⫹ e ⫺ ⫽ Co(NH3)62⫹ Co(OH)3 ⫹ e ⫺ ⫽ Co(OH)2 ⫹ OH⫺ Co(en)33⫹ ⫹ e ⫺ ⫽ Co(en)32⫹ [en ⫽ ethylenediamine] Co(CN)36⫺ ⫹ e ⫺ ⫽ Co(CN)52⫺ ⫹ CN⫺ Co2⫹ ⫹ 2e ⫺ ⫽ Co Co(NH3)62⫹ ⫹ 2e ⫺ ⫽ Co ⫹ 6NH3 [Co(CO)4]2 ⫹ 2e ⫺ ⫽ 2Co(CO)⫺4

Standard or formal potential

Solution composition

0.373 0.330 0.2323 ⫺0.97 1.70 1.61 1.44 1.28 ⫺2.34

1 HClO4 1 HNO3 0.5 H2SO4 1 HCl

⫺2.923 ⫺1.78 1.201 1.392 1.388 1.175 1.181 1.468 1.45 1.188 1.64 1.584 1.659 0.421 0.890 1.415 1.396 1.36 1.15 1.03 ⫺0.13 ⫺0.424 ⫺0.74 0.90 1.416 1.92 0.058 0.17 ⫺0.2 ⫺0.8 ⫺0.277 ⫺0.422 ⫺0.40

1 NaOH 1 NaOH

0.1 H2SO4 1 HClO4 1 NaOH

7 NH3 0.1 en 0.8 KOH

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TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction

Standard or formal potential

Copper Cu2⫹ ⫹ 2e ⫺ ⫽ Cu Cu2⫹ ⫹ e ⫺ ⫽ Cu⫹ Cu⫹ ⫹ e ⫺ ⫽ Cu Cu2⫹ ⫹ Cl⫺ ⫹ e ⫺ ⫽ CuCl Cu2⫹ ⫹ 2Br ⫺ ⫹ e ⫺ ⫽ CuBr ⫺2 Cu2⫹ ⫹ I⫺ ⫹ e ⫺ ⫹ CuI Cu2⫹ ⫹ 2CN⫺ ⫹ e ⫺ ⫽ Cu(CN)⫺2 Cu(NH3)42⫹ ⫹ e ⫺ ⫽ Cu(NH3)2⫹ ⫹ 2NH3 Cu(en)22⫹ ⫹ e ⫺ ⫽ Cu(en)⫹ ⫹ en Cu(CN)⫺2 ⫹ e ⫺ ⫽ Cu ⫹ 2CN⫺ CuCl23⫺ ⫹ e ⫺ ⫽ Cu ⫹ 3Cl⫺ Cu(NH3)⫹2 ⫹ e ⫺ ⫽ Cu ⫹ 2NH3

0.340 0.159 0.520 0.559 0.52 0.86 1.12 0.10 ⫺0.35 ⫺0.44 0.178 ⫺0.100

Curium Cm4⫹ ⫹ e ⫺ ⫽ Cm3⫹ Cm3⫹ ⫹ 3e ⫺ ⫽ Cm

3.2 ⫺2.06

Dysprosium Dy3⫹ ⫹ 3e ⫺ ⫽ Dy Dy3⫹ ⫹ e ⫺ ⫽ Dy2⫹ Dy2⫹ ⫹ 2e ⫺ ⫽ Dy

⫺2.29 ⫺2.5 ⫺2.2

Einsteinium Es3⫹ ⫹ 3e ⫺ ⫽ Es Es3⫹ ⫹ e ⫺ ⫽ Es2⫹ Es2⫹ ⫹ 2e ⫺ ⫽ Es

⫺2.0 ⫺1.5 ⫺2.2

Erbium Er3⫹ ⫹ 3e ⫺ ⫽ Er

⫺2.32

Europium Eu3⫹ ⫹ 3e ⫺ ⫽ Eu Eu3⫹ ⫹ e ⫺ ⫽ Eu2⫹ Eu2⫹ ⫹ 2e ⫺ ⫽ Eu

⫺1.99 ⫺0.35 ⫺2.80

Fermium Fm3⫹ ⫹ 3e ⫺ ⫽ Fm Fm3⫹ ⫹ e ⫺ ⫽ Fm2⫹ Fm2⫹ ⫹ 2e ⫺ ⫽ Fm

⫺1.96 ⫺1.15 ⫺2.37

Fluorine F2 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ 2HF F2 ⫹ H⫹ ⫹ 2e ⫺ ⫽ HF⫺2 F2 ⫹ 2e ⫺ ⫽ 2F⫺ OF2 ⫹ 3H⫹ ⫹ 4e ⫺ ⫽ HF⫺2 ⫹ H2O Francium Fr ⫹ ⫹ e ⫺ ⫽ Fr

top of rh base of rh

Solution composition

1 KBr

1 NH3

1 HCl

1 HClO4

3.053 2.979 2.87 2.209 ca. ⫺2.9

Gadolinium Gd3⫹ ⫹ 3e ⫺ ⫽ Gd

⫺2.28

Gallium Ga3⫹ ⫹ 3e ⫺ ⫽ Ga Ga3⫹ ⫹ e ⫺ ⫽ Ga2⫹ Ga2⫹ ⫹ 2e ⫺ ⫽ Ga

⫺0.529 ⫺0.65 ⫺0.45

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TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction

Standard or formal potential

Germanium GeO2(tetr) ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ GeO(yellow) ⫹ H2O GeO2(tetr) ⫹ 4H⫹ ⫹ 2e ⫺ ⫽ Ge2⫹ ⫹ 2H2O GeO2(hex) ⫹ 4H⫹ ⫹ 2e ⫺ ⫽ Ge2⫹ ⫹ 2H2O H2GeO3 ⫹ 4H⫹ ⫹ 4e ⫺ ⫽ Ge ⫹ 3H2O Ge4⫹ ⫹ 2e ⫺ ⫽ Ge2⫹ Ge2⫹ ⫹ 2e ⫺ ⫽ Ge GeO ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ Ge ⫹ H2O Ge ⫹ 4H⫹ ⫹ 4e ⫺ ⫽ GeH4

⫺0.255 ⫺0.210 ⫺0.132 0.012 0.0 0.247 ⫺0.255 ⫺0.29

Gold Au3⫹ ⫹ 3e ⫺ ⫽ Au Au3⫹ ⫹ 2e ⫺ ⫽ Au⫹ Au⫹ ⫹ e ⫺ ⫽ Au AuCl⫺4 ⫹ 2e ⫺ ⫽ AuCl2⫺ ⫹ 2Cl⫺ AuBr ⫺4 ⫹ 2e ⫺ ⫽ AuBr2⫺ ⫹ 2Br ⫺ Au(SCN)⫺4 ⫹ 2e ⫺ ⫽ Au(SCN)2⫺ ⫹ 2SCN⫺ AuBr ⫺4 ⫹ 3e ⫺ ⫽ Au ⫹ 4Br ⫺ AuCl⫺4 ⫹ 3e ⫺ ⫽ Au ⫹ 4Cl⫺ Au(SCN)⫺4 ⫹ 3e ⫺ ⫽ Au ⫹ 4SCN⫺ Au(OH)3 ⫹ 3H⫹ ⫹ 3e ⫺ ⫽ Au ⫹ 3H2O AuBr ⫺2 ⫹ e ⫺ ⫽ Au ⫹ 2Br ⫺ AuCl⫺2 ⫹ e ⫺ ⫽ Au ⫹ 2Cl⫺ AuI⫺2 ⫹ e ⫺ ⫽ Au ⫹ 2I⫺ Au(CN)⫺2 ⫹ e ⫺ ⫽ Au ⫹ 2CN⫺ Au(SCN)2 ⫹ e ⫺ ⫽ Au ⫹ 2SCN⫺

1.52 1.36 1.83 0.926 0.802 0.623 0.854 1.002 0.662 1.45 0.960 1.15 0.576 ⫺0.596 0.69

Hafnium Hf 4⫹ ⫹ 4e ⫺ ⫽ Hf HfO2 ⫹ 4H⫹ ⫹ 4e ⫺ ⫽ Hf ⫹ 2H2O

⫺1.70 ⫺1.57

Holmium Ho3⫹ ⫹ 3e ⫺ ⫽ Ho

⫺2.23

Hydrogen 2H⫹ ⫹ 2e ⫺ ⫽ H2 2D⫹ ⫹ 2e ⫺ ⫽ D2 2H2O ⫹ 2e ⫺ ⫽ H2 ⫹ 2OH⫺

0.0000 0.029 ⫺0.828

Indium In3⫹ ⫹ 3e ⫺ ⫽ In In3⫹ ⫹ 2e ⫺ ⫽ In⫹ In⫹ ⫹ e ⫺ ⫽ In

⫺0.338 ⫺0.444 ⫺0.126

Iodine H5IO6 ⫹ H⫹ ⫹ 2e ⫺ ⫽ IO⫺3 ⫹ 3H2O IO⫺3 ⫹ 5H⫹ ⫹ 4e ⫺ ⫽ HIO ⫹ 2H2O HIO3 ⫹ 5H⫹ ⫹ 2Cl⫺ ⫹ 4e ⫺ ⫽ ICl⫺2 ⫹ 3H2O 2IO⫺3 ⫹ 12H⫹ ⫹ 10e ⫺ ⫽ I2(c) ⫹ 3H2O IO⫺3 ⫹ 3H2O ⫹ 6e ⫺ ⫽ I⫺ ⫹ 6OH⫺ 2IBr ⫺2 ⫹ 2e ⫺ ⫽ I2Br ⫺ ⫹ 3Br ⫺ 2IBr ⫺2 ⫹ 2e ⫺ ⫽ I2 (c) ⫹ 4Br ⫺ 2IBr ⫹ 2e ⫺ ⫽ I2Br ⫺ ⫹ Br ⫺ 2IBr ⫹ 2e ⫺ ⫽ I2 ⫹ 2Br ⫺ 2ICl ⫹ 2e ⫺ ⫽ I2(c) ⫹ 2Cl⫺

1.603 1.14 1.214 1.195 0.257 0.821 0.874 0.973 1.02 1.20

Solution composition

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.129

cap height base of text

TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction 2ICl⫺2 ⫹ 2e ⫺ ⫽ I2(c) ⫹ 4Cl⫺ 2ICN ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ I2(c) ⫹ 2HCN 2ICN ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ I2(aq) ⫹ 2HCN 2HIO ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ I2 ⫹ 2H2O HIO ⫹ H⫹ ⫹ 2e ⫺ ⫽ I⫺ ⫹ H2O I⫺3 ⫹ 2e ⫺ ⫽ 3I⫺ I2(aq) ⫹ 2e ⫺ ⫽ 2I⫺ I2(c) ⫹ 2e ⫺ ⫽ 2I⫺ Iridium IrBr26⫺ ⫹ e ⫺ ⫽ IrBr63⫺ IrCl26⫺ ⫹ e ⫺ ⫽ IrCl63⫺ IrI26⫺ ⫹ e ⫺ ⫽ IrI63⫺ IrO2 ⫹ 4H⫹ ⫹ e ⫺ ⫽ Ir 3⫹ ⫹ 2H2O IrO2 ⫹ 4H⫹ ⫹ 4e ⫺ ⫽ Ir ⫹ 2H2O Ir 3⫹ ⫹ 3e ⫺ ⫽ Ir IrCl26⫺ ⫹ 4e ⫺ ⫽ Ir ⫹ 6Cl⫺ IrCl36⫺ ⫹ 3e ⫺ ⫽ Ir ⫹ 6Cl⫺ Iron FeO24⫺ ⫹ 8H⫹ ⫹ 3e ⫺ ⫽ Fe3⫹ ⫹ 4H2O FeO24⫺ ⫹ 2H2O ⫹ 3e ⫺ ⫽ FeO2⫺ ⫹ 4OH⫺ Fe3⫹ ⫹ e ⫺ ⫽ Fe2⫹

Fe(CN)36⫺ ⫹ e⫺ ⫽ Fe(CN)64⫺ Fe(EDTA)⫺ ⫹ e⫺ ⫽ Fe(EDTA)2⫺ Fe(OH)⫺4 ⫹ e⫺ ⫽ Fe(OH)42⫺ Fe2⫹ ⫹ 2e⫺ ⫽ Fe [Fe(CO)4]3 ⫹ 6e⫺ ⫽ 3Fe(CO)24⫺

Standard or formal potential

top of rh base of rh

Solution composition

1.07 0.695 0.609 1.45 0.985 0.536 0.621 0.5355 0.805 0.867 0.49 0.223 0.935 1.156 0.835 0.77 2.2 0.55 0.771 0.70 0.67 0.44 0.361 0.71 0.12 ⫺0.73 ⫺0.44 ⫺0.70

Lanthanum La3⫹ ⫹ 3e⫺ ⫽ La

⫺2.38

Lawrencium Lr3⫹ ⫹ 3e⫺ ⫽ Lr

⫺2.0

Lead Pb4⫹ ⫹ 2e⫺ ⫽ Pb2⫹ PbO2(alpha) ⫹ SO24⫺ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ PbSO4 ⫹ 2H2O PbO2 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Pb2⫹ ⫹ 2H2O PbO2 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ PbO ⫹ H2O PbO2⫺ ⫹ H2O ⫹ 2e⫺ ⫽ HPbO⫺2 ⫹ 3OH⫺ Pb2⫹ ⫹ 2e⫺ ⫽ Pb HPbO⫺2 ⫹ H2O ⫹ 2e⫺ ⫽ Pb ⫹ 3OH⫺ PbHPO4 ⫹ 2e⫺ ⫽ Pb ⫹ HPO24⫺ PbSO4 ⫹ 2e⫺ ⫽ Pb ⫹ SO24⫺ PbF2 ⫹ 2e⫺ ⫽ Pb ⫹ 2F⫺ PbCl2 ⫹ 2e⫺ ⫽ Pb ⫹ 2Cl⫺ PbBr2 ⫹ 2e⫺ ⫽ Pb ⫹ 2Br⫺ PbI2 ⫹ 2e⫺ ⫽ Pb ⫹ 2I⫺ Pb ⫹ 2H⫹ ⫹ 2e⫺ ⫽ PbH2

1.65 1.690 1.46 0.28 0.3 ⫺0.126 ⫺0.54 ⫺0.465 ⫺0.356 ⫺0.344 ⫺0.268 ⫺0.280 ⫺0.365 ⫺1.507

1 H2SO4

10 NaOH 1 HCl 0.5 H2SO4 0.3 H3PO4 1 HCl 0.1 EDTA, pH 4– 6 1 NaOH

2 NaOH

short standard long

DEAN #37261

LEFT

(McGHP)

8.130

INTERACTIVE

top of rh base of rh

SECTION 8

cap height base of text

TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction

Standard or formal potential

Lithium Li⫹ ⫹ e⫺ ⫽ Li Li⫹ ⫹ Hg ⫹ e⫺ ⫽ Li(Hg)

⫺3.040 ⫺2.00

Lutetium Lu3⫹ ⫹ 3e⫺ ⫽ Lu

⫺2.30

Magnesium Mg2⫹ ⫹ 2e⫺ ⫽ Mg Mg(OH)2 ⫹ 2e⫺ ⫽ Mg ⫹ 2OH⫺

⫺2.356 ⫺2.687

Manganese MnO⫺4 ⫹ e⫺ ⫽ MnO42⫺ MnO⫺4 ⫹ 4H⫹ ⫹ 3e⫺ ⫽ MnO2(beta) ⫹ 2H2O MnO⫺4 ⫹ 2H2O ⫹ 3e⫺ ⫽ MnO2 ⫹ 4OH⫺ MnO⫺4 ⫹ 8H⫹ ⫹ 5e⫺ ⫽ Mn2⫹ ⫹ 4H2O MnO24⫺ ⫹ e⫺ ⫽ MnO43⫺ MnO24⫺ ⫹ 2H2O ⫹ 2e⫺ ⫽ MnO2 ⫹ 4OH⫺ MnO34⫺ ⫹ 2H2O ⫹ e⫺ ⫽ MnO2 ⫹ 4OH⫺ MnO2 ⫹ 4H⫹ ⫹ e⫺ ⫽ Mn3⫹ ⫹ 2H2O MnO2(beta) ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Mn2⫹ ⫹ 2H2O Mn3⫹ ⫹ e⫺ ⫽ Mn2⫹ Mn(H2P2O7)33⫺ ⫹ 2H⫹ ⫹ e⫺ ⫽ Mn(H2P2O7)22⫺ ⫹ H4P2O7 Mn(CN)36⫺ ⫹ e⫺ ⫽ Mn(CN)64⫺ Mn2⫹ ⫹ 2e⫺ ⫽ Mn

0.56 1.70 0.60 1.51 0.27 0.62 0.96 0.95 1.23 1.5 1.15 ⫺0.24 ⫺1.17

Mendelevium Md3⫹ ⫹ 3e⫺ ⫽ Md Md3⫹ ⫹ e⫺ ⫽ Md2⫹ Md2⫹ ⫹ 2e⫺ ⫽ Md

⫺1.7 ⫺0.15 ⫺2.4

Mercury 2Hg2⫹ ⫹ 2e⫺ ⫽ Hg22⫹ 2HgCl2 ⫹ 2e⫺ ⫽ Hg2Cl2 ⫹ 2Cl⫺ Hg2⫹ ⫹ 2e⫺ ⫽ Hg(lq) HgO(c,red) ⫹ 2H⫹ ⫹ 2e⫺ ⫽ Hg ⫹ H2O Hg22⫹ ⫹ 2e⫺ ⫽ 2Hg Hg2F2 ⫹ 2e⫺ ⫽ 2Hg ⫹ 2F⫺ Hg2Cl2 ⫹ 2e⫺ ⫽ 2Hg ⫹ 2Cl⫺ Hg2Br2 ⫹ 2e⫺ ⫽ 2Hg ⫹ 2Br⫺ Hg2I2 ⫹ 2e⫺ ⫽ 2Hg ⫹ 2I⫺ Hg2SO4 ⫹ 2e⫺ ⫽ 2Hg ⫹ SO24⫺

0.911 0.63 0.8535 0.926 0.7960 0.656 0.2682 0.1392 ⫺0.0405 0.614

Molybdenum MoO24⫺ ⫹ 4H2O ⫹ 6e⫺ ⫽ Mo ⫹ 8OH⫺ H2MoO4 ⫹ 6H⫹ ⫹ 6e⫺ ⫽ Mo ⫹ 4H2O H2MoO4 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ MoO2 ⫹ 2H2O MoO2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Mo ⫹ 2H2O H2MoO4 ⫹ 6H⫹ ⫹ 3e⫺ ⫽ Mo3⫹ ⫹ 4H2O Mo(CN)38⫺ ⫹ e⫺ ⫽ Mo(CN)84⫺ Mo3⫹ ⫹ 3e⫺ ⫽ Mo

⫺0.913 0.114 0.646 ⫺0.152 0.428 0.725 ⫺0.2

Neodynium Nd3⫹ ⫹ 3e⫺ ⫽ Nd Nd3⫹ ⫹ e⫺ ⫽ Nd2⫹ Nd2⫹ ⫹ 2e⫺ ⫽ Nd

⫺2.32 ⫺2.6 ⫺2.2

Solution composition

0.4 H2P2O27⫺ 1.5 NaCN

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.131

cap height base of text

TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction

Standard or formal potential

Neptunium NpO⫹3 ⫹ 2H⫹ ⫹ e⫺ ⫽ NpO22⫹ ⫹ H2O NpO22⫹ ⫹ e⫺ ⫽ NpO2⫹ NpO22⫹ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Np4⫹ ⫹ 2H2O Np4⫹ ⫹ e⫺ ⫽ Np3⫹ Np4⫹ ⫹ 4e⫺ ⫽ Np Np3⫹ ⫹ 3e⫺ ⫽ Np

2.04 1.34 0.95 0.18 ⫺1.30 ⫺1.79

Nickel NiO24⫺ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ NiO2 ⫹ 2H2O NiO2 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Ni2⫹ ⫹ 2H2O NiO2 ⫹ 2H2O ⫹ 2e⫺ ⫽ Ni(OH)2 ⫹ 2OH⫺ Ni(CN)24⫺ ⫹ e⫺ ⫽ Ni(CN)32⫺ ⫹ CN⫺ Ni2⫹ ⫹ 2e⫺ ⫽ Ni Ni(OH)2 ⫹ 2e⫺ ⫽ Ni ⫹ 2OH⫺ Ni(NH3)62⫹ ⫹ 2e⫺ ⫽ Ni ⫹ 6NH3

1.8 1.593 0.490 ⫺0.401 ⫺0.257 ⫺0.72 ⫺0.49

Niobium Nb2O5 ⫹ 10H⫹ ⫹ 4e⫺ ⫽ 2Nb3⫹ ⫹ 5H2O Nb2O5 ⫹ 10H⫹ ⫹ 10e⫺ ⫽ 2Nb ⫹ 5H2O Nb3⫹ ⫹ 3e⫺ ⫽ Nb

⫺0.1 ⫺0.65 ⫺1.1

Nitrogen 2NO⫺3 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ N2O4 ⫹ 2H2O NO⫺3 ⫹ 3H⫹ ⫹ 2e⫺ ⫽ HNO2 ⫹ H2O N2O4 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2HNO2 HNO2 ⫹ H⫹ ⫹ e⫺ ⫽ NO ⫹ H2O 2HNO2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ N2O(g) ⫹ 3H2O 2HNO2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ H2N2O2 ⫹ 2H2O 2NO ⫹ 2H⫹ ⫹ 2e⫺ ⫽ H2N2O2 2NO ⫹ 2H⫹ ⫹ 2e⫺ ⫽ N2O ⫹ H2O H2N2O2 ⫹ 6H⫹ ⫹ 4e⫺ ⫽ 2HONH⫹3 N2O ⫹ 2H⫹ ⫹ 2e⫺ ⫽ N2 ⫹ H2O N2O ⫹ 6H⫹ ⫹ H2O ⫹ 4e⫺ ⫽ 2HONH⫹3 N2 ⫹ 2H2O ⫹ 4H⫹ ⫹ 2e⫺ ⫽ 2HONH⫹3 N2 ⫹ 5H⫹ ⫹ 4e⫺ ⫽ N2H⫹5 HONH⫹3 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ NH4⫹ ⫹ H2O 2HONH⫹3 ⫹ H⫹ ⫹ 2e⫺ ⫽ N2H5⫹ ⫹ 2H2O N2H⫹5 ⫹ 3H⫹ ⫹ 2e⫺ ⫽ 2NH4⫹ 3N2 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2HN3

0.803 0.94 1.07 0.996 1.297 0.86 0.71 1.59 0.496 1.77 ⫺0.05 ⫺1.87 ⫺0.23 1.35 1.41 1.275 ⫺3.40

Nobelium No3⫹ ⫹ 3e⫺ ⫽ No No3⫹ ⫹ e⫺ ⫽ No2⫹ No2⫹ ⫹ 2e⫺ ⫽ No

⫺1.2 1.4 ⫺2.5

Osmium OsO4(aq) ⫹ 4H⫹ ⫹ 4e⫺ ⫽ OsO2 · 2H2O ⫹ 2H2O OsO4(c, yellow) ⫹ 8H⫹ ⫹ 8e⫺ ⫽ Os ⫹ 4H2O OsO2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Os ⫹ 2H2O OsCl26⫺ ⫹ e⫺ ⫽ OsCl63⫺ OsBr26⫺ ⫹ e⫺ ⫽ OsBr63⫺

0.964 0.85 0.687 0.45 0.35

Oxygen O3 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ O2 ⫹ H2O O3 ⫹ H2O ⫹ 2e⫺ ⫽ O2 ⫹ 2OH⫺

2.075 1.240

top of rh base of rh

Solution composition

1 NaOH

short standard long

DEAN #37261

LEFT

(McGHP)

8.132

INTERACTIVE

top of rh base of rh

SECTION 8

cap height base of text

TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction

Standard or formal potential

O2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ 2H2O O2 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ H2O O2 ⫹ H2O ⫹ 2e⫺ ⫽ HO⫺2 ⫹ OH⫺ H2O2 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2H2O HO⫺2 ⫹ H2O ⫹ 2e⫺ ⫽ 3OH⫺ O2 ⫹ 2H2O ⫹ 4e⫺ ⫽ 4OH⫺

1.229 0.695 ⫺0.076 1.763 0.867 0.401

Palladium PdO3 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ PdO2 ⫹ H2O PdCl26⫺ ⫹ 2e⫺ ⫽ PdCl42⫺ ⫹ 2Cl⫺ PdBr26⫺ ⫹ 2e⫺ ⫽ PdBr42⫺ ⫹ 2Br⫺ PdI26⫺ ⫹ 2e⫺ ⫽ PdI42⫺ ⫹ 2I⫺ Pd2⫹ ⫹ 2e⫺ ⫽ Pd PdCl24⫺ ⫹ 2e⫺ ⫽ Pd ⫹ 4Cl⫺ PdBr24⫺ ⫹ 2e⫺ ⫽ Pd ⫹ 4Br⫺ Pd(NH3)42⫹ ⫹ 2e⫺ ⫽ Pd ⫹ 4NH3 Pd(CN)24⫺ ⫹ 2e⫺ ⫽ Pd ⫹ 4CN⫺

2.030 1.470 0.99 0.48 0.915 0.62 0.49 0.0 ⫺1.35

Phosphorus H3PO4 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ H3PO3 ⫹ H2O 2H3PO4 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ H4P2O6 ⫹ 2H2O H4P2O6 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2H3PO3 H3PO3 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ HPH2O2 ⫹ H2O HPH2O2 ⫹ H⫹ ⫹ e⫺ ⫽ P ⫹ 2H2O H3PO3 ⫹ 3H⫹ ⫹ 3e⫺ ⫽ P ⫹ 3H2O 2P(white) ⫹ 4H⫹ ⫹ 4e⫺ ⫽ P2H4 P2H4 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2PH3 P(white) ⫹ 3H⫹ ⫹ 3e⫺ ⫽ PH3

⫺0.276 ⫺0.933 0.380 ⫺0.499 ⫺0.365 ⫺0.502 ⫺0.100 ⫺0.006 ⫺0.063

Platinum PtO3 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ PtO2 ⫹ H2O PtO2 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ PtO ⫹ H2O PtCl26⫺ ⫹ 2e⫺ ⫽ PtCl42⫺ ⫹ 2Cl⫺ PtBr26⫺ ⫹ 2e⫺ ⫽ PtBr42⫺ ⫹ 2Br⫺ PtI26⫺ ⫹ 2e⫺ ⫽ PtI42⫺ ⫹ 2I⫺ Pt2⫹ ⫹ 2e⫺ ⫽ Pt PtCl24⫺ ⫹ 2e⫺ ⫽ Pt ⫹ 4Cl⫺ PtBr24⫺ ⫹ 2e⫺ ⫽ Pt ⫹ 4Br⫺ Plutonium PuO22⫹ ⫹ e⫺ ⫽ PuO2⫹ PuO22⫹ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Pu4⫹ ⫹ 2H2O Pu4⫹ ⫹ e⫺ ⫽ Pu3⫹ Pu4⫹ ⫹ 4e⫺ ⫽ Pu Pu3⫹ ⫹ 3e⫺ ⫽ Pu Polonium PoO2 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Po2⫹ ⫹ 2H2O Po4⫹ ⫹ 4e⫺ ⫽ Po Po2⫹ ⫹ 2e⫺ ⫽ Po Po ⫹ 2H⫹ ⫹ 2e⫺ ⫽ H2Po

2.0 1.045 0.726 0.613 0.321 1.188 0.758 0.698 1.02 1.04 1.01 0.80 0.50 ⫺1.25 ⫺2.00 1.1 0.73 0.37 ca. ⫺1.0

Solution composition

1 NaOH

1 HCl 1 NH3 1 KCN

1 KBr 1 KI

1 H3PO4 1 HF

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.133

cap height base of text

TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction Potassium K⫹ ⫹ e⫺ ⫽ K K⫹ ⫹ Hg ⫹ e⫺ ⫽ K(Hg)

Standard or formal potential

3.2 ⫺2.35

Promethium Pm3⫹ ⫹ 3e⫺ ⫽ Pm

⫺2.42

Protoactinium PaOOH2⫹ ⫹ 3H⫹ ⫹ e⫺ ⫽ Pa4⫹ ⫹ 2H2O PaOOH2⫹ ⫹ 3H⫹ ⫹ 5e⫺ ⫽ Pa ⫹ 2H2O Pa4⫹ ⫹ 4e⫺ ⫽ Pa

⫺0.10 ⫺1.19 ⫺1.46

Radium Ra2⫹ ⫹ 2e⫺ ⫽ Ra

⫺2.916

Rhenium ReO⫺4 ⫹ 2H⫹ ⫹ e⫺ ⫽ ReO3 ⫹ H2O ReO⫺4 ⫹ 4H⫹ ⫹ 3e⫺ ⫽ ReO2 ⫹ 2H2O ReO⫺4 ⫹ 2H2O ⫹ 3e⫺ ⫽ ReO2 ⫹ 4OH⫺ ReO⫺4 ⫹ 6Cl⫺ ⫹ 8H⫹ ⫹ 3e⫺ ⫽ ReCl62⫺ ⫹ 4H2O 2ReO⫺4 ⫹ 10H⫹ ⫹ 8e⫺ ⫽ Re2O3 ⫹ 5H2O ReO3 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ ReO2 ⫹ H2O ReO2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Re ⫹ 2H2O ReCl26⫺ ⫹ 4e⫺ ⫽ Re ⫹ 6Cl⫺ Re ⫹ e⫺ ⫽ Re⫺

0.768 0.51 ⫺0.594 0.12 ⫺0.808 0.63 0.22 0.51 ⫺0.10

Rubidium Rb⫹ ⫹ e⫺ ⫽ Rb Rb⫹ ⫹ Hg ⫹ e⫺ ⫽ Rb(Hg) Ruthenium RuO4 ⫹ e⫺ ⫽ RuO⫺4 RuO4 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ RuO2 ⫹ 2H2O RuO4 ⫹ 8H⫹ ⫹ 8e⫺ ⫽ Ru ⫹ 4H2O RuO⫺4 ⫹ e⫺ ⫽ RuO42⫺ RuO24⫺ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ RuO2 ⫹ 2H2O RuO2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Ru ⫹ 2H2O Ru(H2O)36⫹ ⫹ e⫺ ⫽ Ru(H2O)62⫹ Ru(NH3)36⫹ ⫹ e⫺ ⫽ Ru(NH3)62⫹ Ru(CN)36⫺ ⫹ e⫺ ⫽ Ru(CN)64⫺ Ru3⫹ ⫹ e⫺ ⫽ Ru2⫹

Solution composition

⫺2.924 ca. ⫺1.9

Praseodymium Pr4⫹ ⫹ e⫺ ⫽ Pr3⫹ Pr3⫹ ⫹ e⫺ ⫽ Pr

Rhodium RhO2 ⫹ 4H⫹ ⫹ e⫺ ⫽ Rh3⫹ ⫹ 2H2O Rh3⫹ ⫹ 3e⫺ ⫽ Rh RhCl36⫺ ⫹ 3e⫺ ⫽ Rh ⫹ 6Cl⫺

top of rh base of rh

1.881 0.76 0.5 ⫺2.924 ⫺1.81 0.89 1.4 1.04 0.593 2.0 0.68 0.249 0.10 0.86 0.249

Samarium Sm3⫹ ⫹ 3e⫺ ⫽ Sm Sm3⫹ ⫹ e⫺ ⫽ Sm2⫹ Sm2⫹ ⫹ 2e⫺ ⫽ Sm

⫺2.30 ⫺1.55 ⫺2.67

Scandium Sc3⫹ ⫹ 3e⫺ ⫽ Sc

⫺2.03

short standard long

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TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction

Standard or formal potential

Selenium SeO24⫺ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ H2SeO3 ⫹ H2O H2SeO3 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Se ⫹ 3H2O Se(c) ⫹ 2H⫹ ⫹ 2e⫺ ⫽ H2Se(aq) Se ⫹ H⫹ ⫹ 2e⫺ ⫽ HSe⫺ Se ⫹ 2e⫺ ⫽ Se2⫺

1.151 0.74 ⫺0.115 ⫺0.227 ⫺0.670

Silicon SiO2(quartz) ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Si ⫹ 2H2O SiO2 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ SiO ⫹ H2O SiO2 ⫹ 8H⫹ ⫹ 8e⫺ ⫽ SiH4 ⫹ 2H2O SiF26⫺ ⫹ 4e⫺ ⫽ Si ⫹ 6F⫺ SiO ⫹ 2H⫹ ⫹ 2e⫺ ⫽ Si ⫹ H2O Si ⫹ 4H⫹ ⫹ 4e⫺ ⫽ SiH4(g)

⫺0.909 ⫺0.967 ⫺0.516 ⫺1.37 ⫺0.808 ⫺0.143

Silver AgO⫹ ⫹ 2H⫹ ⫹ e⫺ ⫽ Ag2⫹ ⫹ H2O Ag2O3 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2AgO ⫹ H2O Ag2O3 ⫹ H2O ⫹ 2e⫺ ⫽ 2AgO ⫹ 2OH⫺ Ag2O3 ⫹ 6H⫹ ⫹ 4e⫺ ⫽ 2Ag⫹ ⫹ 3H2O Ag2⫹ ⫹ e⫺ ⫽ Ag⫹ AgO ⫹ 2H⫹ ⫹ e⫺ ⫽ Ag⫹ ⫹ H2O Ag⫹ ⫹ e⫺ ⫽ Ag Ag2SO4 ⫹ 2e⫺ ⫽ 2Ag ⫹ SO24⫺ Ag2C2O4 ⫹ 2e⫺ ⫽ 2Ag ⫹ C2O24⫺ Ag2CrO4 ⫹ 2e⫺ ⫽ 2Ag ⫹ CrO24⫺ Ag(NH3)⫹2 ⫹ e⫺ ⫽ Ag ⫹ 2NH3 AgCl ⫹ e⫺ ⫽ Ag ⫹ Cl⫺ AgBr ⫹ e⫺ ⫽ Ag ⫹ Br⫺ AgCN ⫹ e⫺ ⫽ Ag ⫹ CN⫺ AgI ⫹ e⫺ ⫽ Ag ⫹ I⫺ Ag(CN) ⫹ e⫺ ⫽ Ag ⫹ 2CN⫺ AgSCN ⫹ e⫺ ⫽ Ag ⫹ SCN⫺ Ag2S ⫹ 2e⫺ ⫽ 2Ag ⫹ S2⫺

1.360 1.569 0.739 1.670 1.980 1.772 0.7991 0.653 0.47 0.447 0.373 0.2223 0.071 ⫺0.017 ⫺0.152 ⫺0.31 0.09 ⫺0.71

Sodium Na⫹ ⫹ e⫺ ⫽ Na Na⫹ ⫹ Hg ⫹ e⫺ ⫽ Na(Hg)

⫺2.713 ⫺1.84

Strontium SrO2 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Sr2⫹ Sr2⫹ ⫹ 2e⫺ ⫽ Sr

2.33 ⫺2.89

Sulfur S2O28⫺ ⫹ 2e⫺ ⫽ 2SO42⫺ S2O28⫺ ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2HSO4⫺ 2SO24⫺ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ S2O62⫺ ⫹ 2H2O SO24⫺ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ SO2(aq) ⫹ H2O SO24⫺ ⫹ H2O ⫹ 2e⫺ ⫽ SO32⫺ ⫹ 2OH⫺ S2O62⫺ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ 2H2SO3 S2O26⫺ ⫹ 2e⫺ ⫽ 2SO32⫺ 2HSO⫺3 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ S2O42⫺ ⫹ 2H2O 2SO23⫺ ⫹ 2H2O ⫹ 2e⫺ ⫽ S2O42⫺ ⫹ 4OH⫺ 4H2SO3 ⫹ 4H⫹ ⫹ 6e⫺ ⫽ S4O26⫺ ⫹ 6H2O

1.96 2.08 ⫺0.25 0.158 ⫺0.936 0.569 0.037 0.099 ⫺1.13 0.507

Solution composition

1 NaOH

1 NaOH

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.135

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TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction 4HSO⫺3 ⫹ 8H⫹ ⫹ 6e⫺ ⫽ S4O62⫺ ⫹ 6H2O 2SO2(aq) ⫹ 2H⫹ ⫹ 4e⫺ ⫽ S2O23⫺ ⫹ H2O 2SO23⫺ ⫹ 3H2O ⫹ 4e⫺ ⫽ S2O32⫺ ⫹ 6OH⫺ SO23⫺ ⫹ 3H2O ⫹ 4e⫺ ⫽ S ⫹ 6OH⫺ S4O26⫺ ⫹ 2e⫺ ⫽ 2S2O32⫺ S2O23⫺ ⫹ 6H⫹ ⫹ 4e⫺ ⫽ 2S ⫹ 3H2O SF4(g) ⫹ 4e⫺ ⫽ S ⫹ 4F⫺ S2Cl2(g) ⫹ 2e⫺ ⫽ 2S ⫹ 2Cl⫺ S ⫹ H⫹ ⫹ 2e⫺ ⫽ HS⫺ S ⫹ 2H⫹ ⫹ 2e⫺ ⫽ H2S(aq) S ⫹ 2H⫹ ⫹ 2e⫺ ⫽ H2S(g) S ⫹ 2e⫺ ⫽ S2⫺ Tantalum Ta2O5 ⫹ 10H⫹ ⫹ 10e⫺ ⫽ 2Ta ⫹ 5H2O TaF27⫺ ⫹ 5e⫺ ⫽ Ta ⫹ 7F⫺ Technetium TcO⫺4 ⫹ 4H⫹ ⫹ 3e⫺ ⫽ TcO2 ⫹ 2H2O TcO⫺4 ⫹ 2H⫹ ⫹ e⫺ ⫽ TcO3 ⫹ H2O TcO⫺4 ⫹ e⫺ ⫽ TcO42⫺ TcO⫺4 ⫹ 8H⫹ ⫹ 7e⫺ ⫽ Tc ⫹ 4H2O TcO24⫺ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ TcO2 ⫹ 2H2O TcO2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Tc ⫹ 2H2O Tc ⫹ e⫺ ⫽ Tc⫺

Standard or formal potential 0.577 0.400 ⫺0.576 ⫺0.59 0.080 0.5 0.97 1.19 0.287 0.144 0.174 ⫺0.407

Terbium Tb3⫹ ⫹ 3e⫺ ⫽ Tb

⫺2.31

Thorium Th4⫹ ⫹ 4e⫺ ⫽ Th

1 NaOH 1 NaOH

0.738 0.700 0.569 0.472 1.39 0.272 ca. ⫺0.5 0.929 1.02 0.897 0.559 0.589 0.827 ⫺0.415 0.521 ⫺0.740 ⫺0.817 ⫺0.794

Tl3⫹ ⫹ 3e⫺ ⫽ Tl Tl⫹ ⫹ e⫺ ⫽ Tl TlCl ⫹ e⫺ ⫽ Tl ⫹ Cl⫺ TlBr ⫹ e⫺ ⫽ Tl ⫹ Br⫺ TlI ⫹ e⫺ ⫽ Tl ⫹ I⫺

Solution composition

⫺0.81 ⫺0.45

Tellurium H2TeO4 ⫹ 6H ⫹ ⫹ 2e⫺ ⫽ Te4 ⫹ ⫹ 4H2O H2TeO4 ⫹ 2H ⫹ ⫹ 2e⫺ ⫽ TeO2(c) ⫹ 2H2O TeO24⫺ ⫹ 2H⫹ ⫹ 2e⫺ ⫽ TeO32⫺ ⫹ H2O TeOOH⫹ ⫹ 3H⫹ ⫹ 4e⫺ ⫽ Te ⫹ 2H2O H2TeO3 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Te ⫹ 3H2O TeO23⫺ ⫹ 6H⫹ ⫹ 4e⫺ ⫽ Te ⫹ 3H2O TeO23⫺ ⫹ 3H2O ⫹ 4e⫺ ⫽ Te ⫹ 6OH⫺ TeO2(c) ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Te ⫹ 2H2O Te ⫹ 2H⫹ ⫹ 2e⫺ ⫽ H2Te(aq) Te ⫹ H⫹ ⫹ 2e⫺ ⫽ HTe⫺ Te2⫺ ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2HTe⫺

Thallium Tl3⫹ ⫹ 2e⫺ ⫽ Tl⫹

top of rh base of rh

1.25 0.77 0.72 ⫺0.336 ⫺0.557 ⫺0.658 ⫺0.752 ⫺1.83

1 HClO4 1 HCl

short standard long

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(McGHP)

8.136

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TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued)

Half-reaction

Standard or formal potential

Thullium Tm3⫹ ⫹ 3e⫺ ⫽ Tm

⫺2.32

Tin Sn4⫹ ⫹ 2e⫺ ⫽ Sn2⫹ SnCl26⫺ ⫹ 2e⫺ ⫽ SnCl42⫺ ⫹ 2Cl⫺ SnO23⫺ ⫹ 6H⫹ ⫹ 2e⫺ ⫽ Sn2⫹ ⫹ 3H2O SnF26⫺ ⫹ 4e⫺ ⫽ Sn ⫹ 6F⫺ Sn2⫹ ⫹ 2e⫺ ⫽ Sn SnCl24⫺ ⫹ 2e⫺ ⫽ Sn ⫹ 4Cl⫺ HSnO⫺2 ⫹ H2O ⫹ 2e⫺ ⫽ Sn ⫹ 3OH⫺ Sn ⫹ 4H⫹ ⫹ 4e⫺ ⫽ SnH4

0.154 0.14 0.849 ⫺0.200 ⫺0.1375 ⫺0.19 ⫺0.91 ⫺1.07

Titanium TiO2⫹ ⫹ 2H⫹ ⫹ e⫺ ⫽ Ti3⫹ ⫹ H2O TiO2⫹ ⫹ 2H⫹ ⫹ 4e⫺ ⫽ Ti ⫹ H2O Ti3⫹ ⫹ e⫺ ⫽ Ti2⫹ Ti3⫹ ⫹ 3e⫺ ⫽ Ti Ti2⫹ ⫹ 2e⫺ ⫽ Ti

⫺0.10 ⫺0.86 ⫺0.37 ⫺1.21 ⫺1.63

Tungsten 2WO3 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ W2O5 ⫹ H2O WO3 ⫹ 6H⫹ ⫹ 6e⫺ ⫽ W ⫹ 3H2O WO24⫺ ⫹ 4H2O ⫹ 6e⫺ ⫽ W ⫹ 8OH⫺ WO24⫺ ⫹ 2H2O ⫹ 2e⫺ ⫽ WO2 ⫹ 4OH⫺ W2O5 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2WO2 ⫹ H2O W(CN)38⫺ ⫹ e⫺ ⫽ W(CN)84⫺ WO2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ W ⫹ 2H2O WO2 ⫹ 2H2O ⫹ 4e⫺ ⫽ W ⫹ 4OH⫺

⫺0.029 ⫺0.090 ⫺1.074 ⫺1.259 ⫺0.031 0.457 ⫺0.119 ⫺0.982

Uranium UO22⫹ ⫹ e⫺ ⫽ UO2⫹ UO22⫹ ⫹ 4H⫹ ⫹ 2e⫺ ⫽ U4⫹ ⫹ 2H2O UO⫹2 ⫹ 4H⫹ ⫹ e⫺ ⫽ U4⫹ ⫹ 2H2O U4⫹ ⫹ e⫺ ⫽ U3⫹ U4⫹ ⫹ 4e⫺ ⫽ U U3⫹ ⫹ 3e⫺ ⫽ U

0.16 0.27 0.38 ⫺0.52 ⫺1.38 ⫺1.66

Vanadium VO⫹2 ⫹ 2H⫹ ⫹ e⫺ ⫽ VO2⫹ ⫹ H2O VO⫹2 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ V3⫹ ⫹ 2H2O VO⫹2 ⫹ 4H⫹ ⫹ 3e⫺ ⫽ V2⫹ ⫹ 2H2O VO⫹2 ⫹ 4H⫹ ⫹ 5e⫺ ⫽ V ⫹ 4H2O VO2⫹ ⫹ 2H⫹ ⫹ e⫺ ⫽ V3⫹ ⫹ H2O V3⫹ ⫹ e⫺ ⫽ V2⫹ V2⫹ ⫹ 2e⫺ ⫽ V

1.000 0.668 0.361 ⫺0.236 0.337 ⫺0.255 ⫺1.13

Xenon H4XeO6 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ XeO3 ⫹ 3H2O HXeO36⫺ ⫹ 2H2O ⫹ e⫺ ⫽ HXeO4 ⫹ 4OH⫺ XeO3 ⫹ 6H⫹ ⫹ 2F⫺ ⫹ 4e⫺ ⫽ XeF2 ⫹ 3H2O XeO3 ⫹ 6H⫹ ⫹ 6e⫺ ⫽ Xe(g) ⫹ 3H2O XeF2 ⫹ e⫺ ⫽ XeF ⫹ F⫺ XeF2 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ Xe(g) ⫹ 2HF XeF ⫹ e⫺ ⫽ Xe(g) ⫹ F⫺

2.42 0.9 1.6 2.10 0.9 2.64 3.4

Solution composition

1 HCl

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.137

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TABLE 8.27 Potentials of the Elements and Their Compounds at 25⬚C (Continued) Standard or formal potential

Half-reaction Ytterbium Yb3⫹ ⫹ e⫺ ⫽ Yb2⫹ Yb2⫹ ⫹ 2e⫺ ⫽ Yb Yb3⫹ ⫹ 3e⫺ ⫽ Yb

⫺1.05 ⫺2.8 ⫺2.22

Yttrium Y3⫹ ⫹ 3e⫺ ⫽ Y

⫺2.37

Zinc Zn2⫹ ⫹ 2e⫺ ⫽ Zn Zn(NH3)42⫹ ⫹ 2e⫺ ⫽ Zn ⫹ 4NH3 Zn(CN)24⫺ ⫹ 2e⫺ ⫽ Zn ⫹ 4CN⫺ Zn(tartrate)64⫺ ⫹ 2e⫺ ⫽ Zn ⫹ 4(tartrate)2⫺ Zn(OH)24⫺ ⫹ 2e⫺ ⫽ Zn ⫹ 4OH⫺

⫺0.7626 ⫺1.04 ⫺1.34 ⫺1.15 ⫺1.285

Zirconium Zr4⫹ ⫹ 4e⫺ ⫽ Zr ZrO2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Zr ⫹ 2H2O

⫺1.55 ⫺1.45

top of rh base of rh

Solution composition

TABLE 8.28 Potentials of Selected Half-Reactions at 25⬚C A summary of oxidation-reduction half-reactions arranged in order of decreasing oxidation strength and useful for selecting reagent systems. Half-reaction F2(g) ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2HF O3 ⫹ H2O ⫹ 2e⫺ ⫽ O2 ⫹ 2OH⫺ O3 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ O2 ⫹ H2O Ag2⫹ ⫹ e⫺ ⫽ Ag⫹ S2O28⫺ ⫹ 2e⫺ ⫽ 2SO42⫺ HN3 ⫹ 3H⫹ ⫹ 2e⫺ ⫽ NH⫹4 ⫹ N2 H2O2 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2H2O Ce4⫹ ⫹ e⫺ ⫽ Ce3⫹ MnO⫺4 ⫹ 4H⫹ ⫹ 3e⫺ ⫽ MnO2(c) ⫹ 2H2O 2HClO ⫹ 2H⫹ ⫹ 2e⫺ ⫽ Cl2 ⫹ H2O 2HBrO ⫹ 2H⫹ ⫹ 2e⫺ ⫽ Br2 ⫹ H2O H5IO6 ⫹ H⫹ ⫹ 2e⫺ ⫽ IO3⫺ ⫹ 3H2O NiO2 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Ni2⫹ ⫹ 2H2O Bi2O4(bismuthate) ⫹ 4H⫹ ⫹ 2e⫺ ⫽ 2BiO⫹ ⫹ 2H2O MnO⫺4 ⫹ 8H⫹ ⫹ 5e⫺ ⫽ Mn2⫹ ⫹ 4H2O 2BrO⫺3 ⫹ 12H⫹ ⫹ 10e⫺ ⫽ Br2 ⫹ 6H2O PbO2 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Pb2⫹ ⫹ 2H2O Cr2O27⫺ ⫹ 14H⫹ ⫹ 6e⫺ ⫽ 2Cr3⫹ ⫹ 7H2O Cl2 ⫹ 2e⫺ ⫽ 2Cl⫺ 2HNO2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ N2O ⫹ 3H2O N2H⫹5 ⫹ 3H⫹ ⫹ 2e⫺ ⫽ 2NH4⫹ MnO2 ⫹ 4H⫹ ⫹ 2e⫺ ⫽ Mn2⫹ ⫹ 2H2O O2 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ 2H2O ClO⫺4 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ ClO3⫺ ⫹ H2O

E⬚, volts 3.053 1.246 2.075 1.980 1.96 1.96 1.763 1.72 1.70 1.630 1.604 1.603 1.593 1.59 1.51 1.478 1.468 1.36 1.3583 1.297 1.275 1.23 1.229 1.201

short standard long

DEAN #37261

8.138

LEFT

(McGHP)

INTERACTIVE

top of rh base of rh

SECTION 8

cap height base of text

TABLE 8.28 Potentials of Selected Half-Reactions at 25⬚C (Continued) Half-reaction 2IO⫺3 ⫹ 12H⫹ ⫹ 10e⫺ ⫽ I2 ⫹ 3H2O N2O4 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ 2HNO3 2ICl⫺2 ⫹ 2e⫺ ⫽ 4Cl⫺ ⫹ I2 Br2(1q) ⫹ 2e⫺ ⫽ 2Br⫺ N2O4 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ 2NO ⫹ 2H2O HNO2 ⫹ H⫹ ⫹ e⫺ ⫽ NO ⫹ H2O NO⫺3 ⫹ 4H⫹ ⫹ 3e⫺ ⫽ NO ⫹ 2H2O NO⫺3 ⫹ 3H⫹ ⫹ 2e⫺ ⫽ HNO2 ⫹ H2O 2Hg2⫹ ⫹ 2e⫺ ⫽ Hg22⫹ Cu2⫹ ⫹ I⫺ ⫹ e⫺ ⫽ CuI OsO4(c) ⫹ 8H⫹ ⫹ 8e⫺ ⫽ Os ⫹ 4H2O Ag⫹ ⫹ e⫺ ⫽ Ag Hg22⫹ ⫹ 2e⫺ ⫽ 2Hg Fe3⫹ ⫹ e⫺ ⫽ Fe2⫹ H2SeO3 ⫹ 4H⫹ ⫹ 4e⫺ ⫽ Se ⫹ 3H2O HN3 ⫹ 11H⫹ ⫹ 8e⫺ ⫽ 2NH4⫹ O2 ⫹ 2H⫹ ⫹ 2e⫺ ⫽ H2O2 Ag2SO4 ⫹ 2e⫺ ⫽ 2Ag ⫹ SO42⫺ Cu2⫹ ⫹ Br⫺ ⫹ e⫺ ⫽ CuBr(c) Au(SCN)⫺4 ⫹ 3e⫺ ⫽ Au ⫹ 4SCN⫺ 2HgCl2 ⫹ 2e ⫺ ⫽ Hg2Cl2 (c) ⫹ 2Cl⫺ Sb2O5 ⫹ 6H ⫹ ⫹ 4e ⫺ ⫽ 2SbO⫹ ⫹ 3H2O H3AsO4 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ HAsO2 ⫹ 2H2O TeOOH⫹ ⫹ 3H⫹ ⫹ 4e ⫺ ⫽ Te ⫹ 2H2O Cu 2⫹ ⫹ Cl ⫺ ⫹ e ⫺ ⫽ CuCl(c) I ⫺3 ⫹ 2e ⫺ ⫽ 3I ⫺ I2 ⫹ 2e ⫺ ⫽ 2I⫺ Cu⫹ ⫹ e ⫺ ⫽ Cu 4H2SO3 ⫹ 4H⫹ ⫹ 6e ⫺ ⫽ S4O26⫺ ⫹ 6H2O Ag2 CrO4 ⫹ 2e ⫺ ⫽ 2Ag ⫹ CrO24⫺ 2H2SO3 ⫹ 2H⫹ ⫹ 4e ⫺ ⫽ S2O23⫺ ⫹ 3H2O UO ⫹2 ⫹ 4H⫹ ⫹ e ⫺ ⫽ U4⫹ ⫹ 2H2O Fe(CN) 36⫺ ⫹ e ⫺ ⫽ Fe(CN) 64⫺ Cu2⫹ ⫹ 2e ⫺ ⫽ Cu VO2⫹ ⫹ 2H⫹ ⫹ e⫺ ⫽ V3⫹ ⫹ H2O BiO⫹ ⫹ 2H⫹ ⫹ 3e ⫺ ⫽ Bi ⫹ H2O UO 22⫹ ⫹ 4H⫹ ⫹ 2e ⫺ ⫽ U4⫹ ⫹ 2H2O Hg2Cl2(c) ⫹ 2e ⫺ ⫽ 2Hg ⫹ 2Cl⫺ AgCl ⫹ e ⫺ ⫽ Ag ⫹ Cl⫺ SbO⫹ ⫹ 2H⫹ ⫹ 3e ⫺ ⫽ Sb ⫹ H2O CuCl 23⫺ ⫹ e ⫺ ⫽ Cu ⫹ 3Cl⫺ SO 24⫺ ⫹ 4H⫹ ⫹ 2e ⫺ ⫽ H2SO3 ⫹ H2O Sn4⫹ ⫹ 2e ⫺ ⫽ Sn2⫹ S ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ H2S Hg2Br2(c) ⫹ 2e⫺ ⫽ 2Hg ⫹ 2Br⫺ CuCl ⫹ e ⫺ ⫽ Cu ⫹ Cl⫺ TiO 2⫹ ⫹ 2H⫹ ⫹ e ⫺ ⫽ Ti3⫹ ⫹ H2O S4O 26⫺ ⫹ 2e ⫺ ⫽ 2S2 O32⫺ AgBr ⫹ e ⫺ ⫽ Ag ⫹ Br ⫺ HCOOH ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ HCHO ⫹ H2O CuBr ⫹ e ⫺ ⫽ Cu ⫹ Br⫺ 2H⫹ ⫹ 2e ⫺ ⫽ H2 Hg2 I2 ⫹ 2e ⫺ ⫽ 2Hg ⫹ 2I ⫺

E⬚, volts 1.195 1.07 1.07 1.065 1.039 0.996 0.957 0.94 0.911 0.861 0.84 0.7991 0.7960 0.771 0.739 0.695 0.695 0.654 0.654 0.636 0.63 0.605 0.560 0.559 0.559 0.536 0.536 0.53 0.507 0.449 0.400 0.38 0.361 0.340 0.337 0.32 0.27 0.2676 0.2223 0.212 0.178 0.158 0.15 0.144 0.1392 0.121 0.100 0.08 0.0711 0.056 0.033 0.0000 ⫺0.0405

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.139

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TABLE 8.28 Potentials of Selected Half-Reactions at 25⬚C (Continued) Half-reaction Pb 2⫹ ⫹ 2e ⫺ ⫽ Pb Sn 2⫹ ⫹ 2e ⫺ ⫽ Sn AgI ⫹ e ⫺ ⫽ Ag ⫹ I ⫺ N2 ⫹ 5H⫹ ⫹ 4e ⫺ ⫽ N2H⫹5 V 3⫹ ⫹ e ⫺ ⫽ V 2⫹ Ni2⫹ ⫹ 2e ⫺ ⫽ Ni Co2⫹ ⫹ 2e ⫺ ⫽ Co Ag(CN) ⫺2 ⫹ e ⫺ ⫽ Ag ⫹ 2CN⫺ PbSO4 ⫹ 2e ⫺ ⫽ Pb ⫹ SO 24⫺ Cd 2⫹ ⫹ 2e ⫺ ⫽ Cd Cr 3⫹ ⫹ e ⫺ ⫽ Cr 2⫹ Fe 2⫹ ⫹ 2e ⫺ ⫽ Fe H3 PO3 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ HPH2O2 ⫹ H2O 2CO2 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ H2C2O4 U4⫹ ⫹ e ⫺ ⫽ U 3⫹ Zn 2⫹ ⫹ 2e ⫺ ⫽ Zn Mn2⫹ ⫹ 2e ⫺ ⫽ Mn Al3⫹ ⫹ 3e ⫺ ⫽ Al Mg2⫹ ⫹ 2e ⫺ ⫽ Mg Na⫹ ⫹ e ⫺ ⫽ Na K⫹ ⫹ e⫺ ⫽ K Li⫹ ⫹ e⫺ ⫽ Li 3N2 ⫹ 2H⫹ ⫹ 2e ⫺ ⫽ 2HN3

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E⬚, volts ⫺0.125 ⫺0.136 ⫺0.1522 ⫺0.225 ⫺0.255 ⫺0.257 ⫺0.277 ⫺0.31 ⫺0.3505 ⫺0.4025 ⫺0.424 ⫺0.44 ⫺0.499 ⫺0.49 ⫺0.52 ⫺0.7626 ⫺1.18 ⫺1.67 ⫺2.356 ⫺2.714 ⫺2.925 ⫺3.045 ⫺3.10

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TABLE 8.29 Overpotentials for Common Electrode Reactions at 25⬚C The overpotential is defined as the difference between the actual potential of an electrode at a given current density and the reversible electrode potential for the reaction. Current Density, A/cm2 Electrode

0.001

0.01

0.1

0.5

1.0

5.0

0.69

1.22

0.48 1.29 0.24 0.78 1.25

0.35 0.82 0.32 1.03

0.48 1.29 0.60 1.07

0.55

Overpotential, volts Liberation of H2 from 1M H2SO4 Ag 0.097 Al 0.3 Au 0.017 Bi 0.39 Cd Co Cr Cu Fe Graphite 0.002 Hg 0.8 Ir 0.0026 Ni 0.14 Pb 0.40 Pd 0 Pt (smooth) 0.0000 Pt (platinized) 0.0000 Sb Sn Ta Zn 0.48

0.93 0.2 0.3 0.4 0.04 0.16 0.030 0.4 0.5 0.39 0.75

Liberation of O2 from 1M KOH Ag 0.58 Au 0.67 Cu 0.42 Graphite 0.53 Ni 0.35 Pt (smooth) 0.72 Pt (platinized) 0.40

0.73 0.96 0.58 0.90 0.52 0.85 0.52

0.13 0.83 0.4 1.13 0.2 0.4 0.56

0.3 1.00 0.1

0.33 0.98

0.73

0.56 0.52

0.71 1.06

0.29 0.041

0.68 0.048

0.051

1.2 0.4 1.06

1.23

0.98 1.24 0.66 1.09 0.73 1.28 0.64

1.13 1.63 0.79 1.24 0.85 1.49 0.77

Liberation of Cl2 from saturated NaCl solution Graphite Platinized Pt 0.006 Smooth Pt 0.008 0.03

0.25 0.026 0.054

0.42 0.05 0.161

0.236

Liberation of Br2 from saturated NaBr solution Graphite 0.002 Platinized Pt 0.002 Smooth Pt 0.002

0.027 0.012 0.006*

0.16 0.069 0.26

0.33 0.21 0.38†

Liberation of I2 from saturated Nal solution Graphite 0.002 0.014 Platinized Pt 0.006 Smooth Pt 0.003

0.097 0.032 0.03

0.12

0.196 0.22

0.53

* At 0.23 A/cm2. † At 0.72 A/cm2. The overpotential required for the evolution of O2 from dilute solutions of HClO4 , HNO3 , H3PO4 or H2SO4 onto smooth platinum electrodes is approximately 0.5 V.

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TABLE 8.30 Half-Wave Potentials of Inorganic Materials All values are in volts vs. the saturated calomel electrode. Element Aluminum 3⫹

E1/2 , volts

Solvent system

⫺0.5

0.2M acetate, pH 4.5– 4.7, plus 0.07% azo dye Pontochrome Violet SW; reduction wave of complexed dye is 0.2 V more negative than that of the free dye.

5⫹

⫺0.15 ⫺0.31(1) ⫺0.8 ⫺1.0; ⫺1.2 ⫺1.26 ⫺1.32 0.0; ⫺0.257

5⫹ to 0

⫺0.35

1M HCl 1M HNO3 (or 0.5M H2SO4 ) 0.5M tartrate, pH 4.5 0.5M tartrate, pH 9 (waves not distinct) 1M NaOH; also anodic wave (3⫹ to 5⫹) at ⫺0.45 0.5M tartrate plus 0.1M NaOH 6M HCl. First wave (5⫹ to 3⫹) starts at the oxidation potential of Hg; second wave is 3⫹ to 0. 1M HCl plus 4M KBr

⫺0.26 ⫺0.8; ⫺1.0 ⫺0.7; ⫺1.0

0.5M KOH (anodic wave); only suitable wave 0.1M HCl; ill-defined waves 0.5M H2SO4 (or 1M HNO3 )

⫺1.94

0.1M (C2 H5 )4 NI

⫺0.025(15) ⫺0.09 ⫺0.29 ⫺0.7 ⫺1.0

1M HNO3 (or 0.5M H2SO4 ) 1M HCl 0.5M tartrate, pH 4.5 0.5M tartrate (pH 9), wave not well-developed 0.5M tartrate plus 0.1M NaOH, poor wave

⫺1.75 0.13 0.0 0.1

0.1M alkali chlorides (or 0.1M NaOH) 0.05M H2SO4 Wave (anodic) starts at zero; Hg2Br2 forms Oxidation of Hg to form mercury(I) bromide

⫺0.60 ⫺0.64 ⫺0.81

0.1M KCl, or 0.5M H2SO4 , or 1M HNO3 0.5M tartrate at pH 4.5 or 9 1M NH4Cl plus 1M NH3

⫺2.22 ⫺2.13

0.1M (C2H5 )4NCl 0.1M (C2 H5 )4 NCl in 80% ethanol

Cerium 3⫹ to 0

⫺1.97

0.02M alkali sulfate

Cesium 1⫹ to 0

⫺2.05

0.1M (C2 H5 )4NOH in 50% ethanol

Antimony 3⫹ to 0

Arsenic 3⫹ to 5⫹ 3⫹ Barium 2⫹ to 0 Bismuth 3⫹ to 0

Bromine 5⫹ to 1⫺ 0 to 1⫺ Br⫺ Cadmium 2⫹ to 0

Calcium 2⫹ to 0

Chlorine Cl⫺ Chromium 6⫹ to 3⫹ 3⫹ to 0 3⫹ to 2⫹

0.25 ⫺0.85 ⫺0.35; ⫺1.70 ⫺0.95

Oxidation of Hg to form Hg2Cl2 CrO 24⫺ to CrO 2⫺ in 0.1 to 1M NaOH 1M NH4Cl 9 NH3 buffer (pH 8– 9); 3⫹ to 2⫹ to 0 0.1M pyridine– 0.1M pyridinium chloride

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TABLE 8.30 Half-Wave Potentials of Inorganic Materials (Continued) Element 2⫹ to 0 2⫹ to 3⫹ Cobalt 3⫹ to 0 2⫹ to 0

3⫹ to 2⫹ Copper 2⫹ to 0

2⫹

E1/2 , volts

Solvent system

⫺1.54 ⫺0.40

1M KCl 1M KCl (anodic wave)

⫺0.5; ⫺1.3 ⫺1.07 ⫺1.03 ⫺1.4 0.0

1M NH4Cl plus 1M NH3 ; 3⫹ to 2⫹ to 0 0.1M pyridine plus pyridinium chloride Neutral 1M potassium thiocyanate Co(H2O) 62⫹ in noncomplexing systems 1M sodium oxalate in acetate buffer (pH 5); diffusion current measured between 0 and ⫺0.1 V

0.04 ⫺0.085 ⫺0.09 ⫺0.20 ⫺0.22 ⫺0.4 ⫺0.568 0.04; ⫺0.22 ⫺0.02; ⫺0.39 0.05; ⫺0.25

0.1M KNO3 , 0.1M NH4ClO4 , or 1M Na2SO4 0.1M Na4P2O7 plus 0.2M Na acetate, pH 4.5 0.5M Na tartrate, pH 4.5 0.1M potassium oxalate, pH 5.7 to 10 0.5M potassium citrate, pH 7.5 0.5M Na tartrate plus 0.1M NaOH (pH 12) 0.1M KNO3 plus 1M ethylenediamine 1M KCl; consecutive waves: 2⫹ to 1⫹ to 0 0.1M KSCN; consecutive waves: 2⫹ to 1⫹ to 0 0.1M pyridine plus 0.1M pyridinium chloride; consecutive waves: 2⫹ to 1⫹ to 0 1M NH4Cl plus 1M NH3 ; consecutive waves

⫺0.24; ⫺0.50 Gallium 3⫹ to 0

⫺1.1

Not more than 0.001M HCl or wave masked by hydrogen wave which immediately follows

Germanium 2⫹ to 0

⫺0.45

6M HCl; prior reduction with HPH2O2 to 2⫹

Gold 3⫹ to 1⫹ 1⫹ to 0

0 ⫺1.4

1M KCN; wave starts at 0 V Au(CN) ⫺2 wave best for analytical purposes

Indium 3⫹ to 0

⫺0.60

1M KCl In Na acetate, pH 3.9 to 4.2

Iodine IO ⫺4 IO ⫺3

⫺0.075 ⫺0.305 ⫺0.500 ⫺0.650 ⫺1.050 ⫺1.20

0 to 1⫺ 1⫺

0.0 ⫺0.1

First wave at pH 0 (shifts to ⫺0.08 at pH 12); second wave corresponds to iodate reduction 0.2M KNO3 (shifts ⫺0.13 V/pH unit increase) 0.1M hydrogen phthalate, pH 3.2 0.1M acetate plus 0.1M KCl, pH 4.9 0.1M citrate, pH 5.95 0.2M phosphate, pH 7.10 0.05M borax ⫹ 0.1M KCl, pH 9.2; or NaOH plus 0.1M KCl, pH 13.0 Wave starts from zero in acid media; Hg2I2 formed Oxidation of Hg to form Hg2I2

⫺0.44; ⫺1.52 ⫺0.17; ⫺1.50 ⫺0.9; ⫺1.5

1M (NH4 )2CO3 ; two waves; 3⫹ to 2⫹ to 0 0.5M Na tartrate, pH 5.8; two waves; 3⫹ to 2⫹ to 0 0.1 to 5M KOH plus 8% mannitol; 3⫹ to 2⫹ to 0

Iron 3⫹

0.36

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TABLE 8.30 Half-Wave Potentials of Inorganic Materials (Continued) Element

E1/2 , volts

0.1M EDTA plus 2M Na acetate, pH 6– 7 0.2M Na oxalate, pH 7.9 or less 0.5M Na citrate, pH 6.5 1M NH4ClO4 0.1M KHF2 , pH 4 or less 0.5M Na citrate, pH 6.5 0.2M Na oxalate, pH 7.9 or less 0.5M Na tartrate, pH 5.8 0.1M KHF2 , pH 4 or less

⫺0.405 ⫺0.435 ⫺0.49(1) ⫺0.72 ⫺0.75

1M HNO3 1M KCl (or HCl) 0.5M Na tartrate, pH 4.5 or 9 1M KCN 1M KOH or 0.5M Na tartrate plus 0.1M NaOH

Lithium 1⫹ to 0

⫺2.31

0.1M (C2H5)4 NOH in 50% ethanol

Magnesium 2⫹ to 0

⫺2.2

0.1M (C2H5)4NCl (poorly defined wave)

⫺1.65 ⫺1.55 ⫺1.33

1M NH4Cl plus 1M NH3 1M KCNS 1.5M KCN

⫺0.26; ⫺0.63

0.3M HCl, two waves: 6⫹ to 5⫹ to 3⫹

⫺0.70 ⫺0.78 ⫺1.09 ⫺1.1 ⫺1.36

1M KSCN 1M KCl plus 0.5M pyridine 1M NH4Cl plus 1M NH3 Ni(H2O)62⫹ in NH4ClO4 or KNO3 Ni(CN)24⫺ in 1M KCN (alkaline media)

Niobium 5⫹ to 3⫹

⫺0.80(4)

1M HNO3

Nitrogen Nitrate HNO2 C2N2 Oxamic acid Cyanide Thiocyanate

⫺1.45 ⫺0.77 ⫺1.2; ⫺1.55 ⫺1.55 ⫺0.45 0.18

0.017M LaCl3 (reduced to hydroxylamine) 0.1M HCl 0.1M Na acetate, two waves 0.1M Na acetate 0.1M NaOH; anodic wave starts at ⫺0.45 Anodic wave; neutral or weakly alkaline medium

0.0; ⫺0.41; ⫺1.16

Sat’d Ca(OH)2 . Three waves: first starts at 0; second wave is OsO24⫺ to Os(V); and third wave is Os(V) to Os(III)

⫺0.05; ⫺0.9

Buffer solutions of pH 1 to 10. Two waves: O2 to H2O2 , and H2O2 to H2O. Second wave extends from ⫺0.5 to ⫺1.3 Very extended wave (see above); sharper in presence of Aerosol OT

2⫹ to 3⫹

Lead 2⫹ to 0

Manganese 2⫹ to 0

Molybdenum 6⫹ Nickel 2⫹ to 0

Osmium OsO4 Oxygen O2

H2O2

⫺0.9

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Solvent system

⫺0.13 ⫺0.27 ⫺0.28 ⫺1.46(2) ⫺1.36 ⫺0.28 ⫺0.27 ⫺0.17 ⫺1.36

3⫹ to 2⫹

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TABLE 8.30 Half-Wave Potentials of Inorganic Materials (Continued) Element Palladium 2⫹ to 0

E1/2 , volts

Solvent system

⫺0.31 ⫺0.64 ⫺0.72

1M pyridine plus 1M KCl 0.1M ethylenediamine plus 1M KCl 1M NH4Cl plus 1M NH3

Potassium 1⫹ to 0

⫺2.10

0.1M (C2H5)4NOH in 50% ethanol

Rhenium 7⫹ to 4⫹ 4⫹ to 3⫹

⫺0.44 ⫺0.51

2M HCl or (better) 4M HClO4 ReCl26⫺ ion in 1M HCl

Rhodium 3⫹ to 2⫹

⫺0.41

1M pyridine plus 1M KCl

Rubidium 1⫹ to 0

⫺1.99

0.1M (C2H5)4NOH in 50% ethanol

Scandium 3⫹ to 0

⫺1.80

0.1M LiCl, KCl, or BaCl2

⫺1.44 ⫺1.54 ⫺0.49 ⫺0.94

1M NH4Cl plus NH3 , pH 8.0 Same system adjusted to pH 9.5 Anodic wave at pH 0 due to HgSe Anodic wave at pH 12 (0.01M NaOH)

Silver 1⫹ to 0 1⫹ to 0

⫺0.3

Wave starts at oxidation potential of Hg 0.0014M KAg(CN)2 without excess cyanide

Sodium 1⫹ to 0

⫺2.07

0.1M (C2H5)4NOH in 50% ethanol

Strontium 2⫹ to 0

⫺2.11

0.1M (C2H5)4NI, water or 80% ethanol

Sulfur SO2 S2O24⫺ S2O23⫺ 0 to 2⫺ HS⫺

⫺0.38 ⫺0.43 ⫺0.15 ⫺0.50 ⫺0.76

1M HNO3 (or other strong acid); 4⫹ to 2⫹ 0.5M (NH4)2HPO4 plus 1M NH3 (anodic wave) 1M strong acid; anodic mercury wave 90% methanol, 9.5% pyridine, 0.5% HCl (pH 6) 0.1M NaOH (anodic mercury wave)

⫺0.4 ⫺0.63 ⫺1.22 ⫺0.72 ⫺0.08

Citrate buffer, pH 1.6 (second of two waves) Ammoniacal buffer, pH 9.4 0.1M NaOH 1M HCl (true anodic reversible wave) 1M NaOH (same as above; intermediate values at pH 1 to 13)

⫺0.48

1M KCl, KNO3 , K2SO4 , KOH, or NH3

⫺0.25; ⫺0.52 ⫺0.59 ⫺1.22 ⫺0.28 ⫺0.73

4M NH4Cl ⫹ 1M HCl; two waves: 4⫹ to 2⫹ to 0 0.5M tartrate, pH 4.3 1M NaOH (stannite ion to tin) 0.5M Na tartrate, pH 4.3 (anodic wave) 1M NaOH (stannite ion to stannate ion)

Selenium 4⫹ to 2⫺ 2⫺

Tellurium 4⫹ to 0 4⫹ to 2⫺ 2⫺ to 0

Thallium 3⫹ to 0 Tin 4⫹ to 2⫹ 2⫹ to 0 2⫹ to 4⫹

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TABLE 8.30 Half-Wave Potentials of Inorganic Materials (Continued) Element Titanium 4⫹ to 3⫹

E1/2 , volts ⫺0.173 ⫺1.22

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Solvent system

0.1M K2C2O4 plus 1M H2SO4 0.4M tartrate, pH 6.5

Tungsten 6⫹

0.0; ⫺0.64

Uranium 6⫹

⫺0.180; ⫺0.92

UO22⫹ to UO2⫹, then U3⫹ in 0.02M HCL

Vanadium 5⫹ to 4⫹ to 2⫹ 4⫹ to 2⫹ 3⫹ to 2⫹ 4⫹ to 5⫹ 4⫹ to 5⫹ 2⫹ to 3⫹

⫺0.97; ⫺1.26 ⫺0.98 ⫺0.55 ⫺0.32 0.76 ⫺0.55

1M NH4Cl plus 1M NH3 and 0.08M Na2SO3 0.05M H2SO4 0.5M H2SO4 1M NH4Cl, 1M NH3 , and 0.08M Na2SO3 0.05M H2SO4 ; anodic wave starting from zero 0.5M H2SO4 ; anodic wave

⫺0.995 ⫺1.01 ⫺1.15 ⫺1.23 ⫺1.33 ⫺1.53

0.1M KCl 0.1M KSCN 0.5M tartrate, pH 9 0.5M tartrate, pH 4.5 1M NH4Cl plus 1M NH3 1M NaOH

Zinc 2⫹ to 0

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6M HCl; two waves: first wave starts at zero and is W(VI) to W(V), the second wave is W(V) to W(III)

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TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C

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The solvent systems in this table are listed below: A, acetonitrile and a perchlorate salt such as LiClO4 or a tetraalkyl ammonium salt B, acetic acid and an alkali acetate, often plus a tetraalkyl ammonium iodide C, 0.05 to 0.175M tetraalkyl ammonium halide and 75% 1,4-dioxane D, buffer plus 50% ethanol (EtOH) Abbreviations Used in the Table Bu, butyl Me, methyl Et, ethyl MeOH, methanol EtOH, ethanol PrOH, propanol M, molar Compound

Solvent system

E1/2

Unsaturated aliphatic hydrocarbons Acrylonitrile Allene

C but 30% EtOH C

⫺1.94 ⫺2.29

1,3-Butadiene

A C C C

⫺2.03 ⫺2.59 ⫺1.89 ⫺2.40

1,4-Cyclohexadiene Cyclohexene 1,3,5,7-Cyclooctatetraene

A A B C

⫺1.6 ⫺1.89 ⫺1.42 ⫺1.51

Diethyl fumarate Diethyl maleate 2,3-Dimethyl-1,3-butadiene Dimethylfulvene Diphenylacetylene 1,1-Diphenylethylene

B, pH 4.0 B, pH 4.0 A C C B C

⫺0.84 ⫺0.95 ⫺1.83 ⫺1.89 ⫺2.20 ⫺1.52 ⫺2.19

Ethyl methacrylate

0.1 N LiCl⫹25% EtOH

⫺1.9

2-Methyl-1,3-butadiene 2-Methyl-1-butene

A A

⫺1.84 ⫺1.97

1-Piperidino-4-cyano-4-phenyl-1,3-butadiene

LiClO4 in dimethylformamide

⫺0.16

trans-Stilbene

B

⫺1.51

Tetrakis(dimethylamino)ethylene

A

⫺0.75

1,3-Butadiyne 1-Buten-2-yne

Aromatic hydrocarbons Acenaphthene

Anthracene

Azulene

A B C A B C A C

⫺0.95 ⫺1.36 ⫺2.58 ⫺0.84 ⫺1.20 ⫺1.94 ⫺0.71 ⫺1.66, ⫺2.26, ⫺2.56

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TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C (Continued) Compound

Solvent system

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E1/2

Aromatic hydrocarbons (continued) 1,2-Benzanthracene 2,3-Benzanthracene Benzene 1,2-Benzo[a]pyrene Biphenyl

C A A A A B C

⫺2.03, ⫺2.54 ⫺0.54, ⫺1.20 ⫺2.08 ⫺0.76 ⫺1.48 ⫺1.91 ⫺2.70

Chrysene

A

⫺1.22

1,2,5,6-Dibenzanthracene 1,2-Dihydronaphthalene 9,10-Dimethylanthracene 2,3-Dimethylnaphthalene 9,10-Diphenylanthracene

A C A A A

⫺1.00, ⫺1.26 ⫺2.57 ⫺0.65 ⫺1.08, ⫺1.34 ⫺0.92

Fluorene

A B C

⫺1.25 ⫺1.65 ⫺2.65

Hexamethylbenzene

A B

⫺1.16 ⫺1.52

Indan Indene

A A C

⫺1.59, ⫺2.02 ⫺1.23 ⫺2.81

1-Methylnaphthalene

A B C A B C

⫺1.24 ⫺1.53 ⫺2.46 ⫺1.22 ⫺1.55 ⫺2.46

Naphthalene

A B

⫺1.34 ⫺1.72

Pentamethylbenzene

A B A B C C A

⫺1.28 ⫺1.62 ⫺1.23 ⫺1.68 ⫺2.46, ⫺2.71 ⫺2.37 ⫺1.06, ⫺1.24

Styrene

B C C

⫺1.51 ⫺2.26 ⫺2.35

1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene Tetraphenylethylene 1,4,5,8-Tetraphenylnaphthalene Toluene 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene

A A C A A A A

⫺1.50, ⫺1.99 ⫺1.29 ⫺2.05 ⫺1.39 ⫺1.98 ⫺1.58 ⫺1.41

2-Methylnaphthalene

Phenanthrene

Phenylacetylene Pyrene trans-Stilbene

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TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C (Continued) Compound

Solvent system

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E1/2

Aromatic hydrocarbons (continued)

Triphenylene Triphenylmethane

A B A C

⫺1.50 ⫺1.90 ⫺1.46, ⫺1.55 ⫺1.01, ⫺1.68, ⫺1.96

o-Xylene m-Xylene p-Xylene

A A A

⫺1.58, ⫺2.04 ⫺1.58 ⫺1.56

1,3,5-Trimethylbenzene

Aldehydes ⫺1.89

Acetaldehyde

B, pH 6.8– 13

Benzaldehyde Bromoacetaldehyde

McIlvaine buffer, pH 2.2 pH 8.5 pH 9.8

⫺0.96, ⫺1.32 ⫺0.40 ⫺1.58, ⫺1.82

Chloroacetaldehyde Cinnamaldehyde Crotonaldehyde

Ammonia buffer, pH 8.4 Buffer ⫹ EtOH, pH 6.0 B, pH 1.3– 2.0 Ammonia buffer, pH 8.0

⫺1.06, ⫺1.66 ⫺0.9, ⫺1.5, ⫺1.7 ⫺0.92 ⫺1.30

Dichloroacetaldehyde 3,7-Dimethyl-2,6-octadienal

Ammonia buffer, pH 8.4 0.1 M Et4NI

⫺1.03, ⫺1.67 ⫺1.56, ⫺2.22

Formaldehyde

0.05 M KOH⫹0.1 M KCl, pH 12.7 pH 1– 8 pH 10

2-Furaldehyde

⫺1.59 ⫺0.86– 0.07 pH ⫺1.43

Phosphate buffer, pH 7 Britton-Robinson buffer, pH 5.0 Britton-Robinson buffer, pH 8.0 0.1 M KOH, pH 13 B, pH 3.4

⫺1.55 ⫺1.47 ⫺1.55 ⫺1.70 ⫺1.41

Britton-Robinson buffer, pH 1.8 Britton-Robinson buffer, pH 6.8 McIlvaine buffer, pH 2.2 McIlvaine buffer, pH 5.0 McIlvaine buffer, pH 8.0

⫺1.16 ⫺1.45 ⫺1.05 ⫺1.16, ⫺1.36 ⫺1.47

Methyl glyoxal

Britton-Robinson buffer, pH 1.8 Britton-Robinson buffer, pH 6.8 Britton-Robinson buffer, pH 1.8 Britton-Robinson buffer, pH 6.8 A, pH 4.5

⫺1.02 ⫺1.49 ⫺1.17 ⫺1.48 ⫺0.83

m-Nitrobenzaldehyde

Buffer⫹10% EtOH, pH 2.0

⫺0.28, ⫺1.20

Phthalaldehyde

Buffer, pH 3.1 Buffer, pH 7.3 pH 4.5 pH 9.0 0.1 M LiOH, pH 13 0.1 M HCl⫹50% EtOH

⫺0.64, ⫺1.07 ⫺0.89, ⫺1.29 ⫺1.36 ⫺1.1 ⫺1.93 ⫺1.25

Glucose Glyceraldehyde Glycolaldehyde Glyoxal 4-Hydroxybenzaldehyde 4-Hydroxy-2-methoxybenzaldehyde

o-Methoxybenzaldehyde p-Methoxybenzaldehyde

2-Propenal (acrolein) Propionaldehyde Pyrrole-2-carbaldehyde

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.149

TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C (Continued) Compound

Solvent system

top of rh base of rh cap height base of text

E1/2

Aldehydes (continued) Salicylaldehyde

McIlvaine buffer, pH 2.2 McIlvaine buffer, pH 5.0 McIlvaine buffer, pH 8.0

⫺0.99, ⫺1.23 ⫺1.20, ⫺1.30 ⫺1.32

Trichloroacetaldehyde

Ammonia buffer, pH 8.4 0.1 M KCl⫹50% EtOH

⫺1.35, ⫺1.66 ⫺1.55

Ketones Acetone Acetophenone

7H-Benz[de]anthracen-7-one Benzil Benzoin Benzophenone Benzoylacetone Bromoacetone 2,3-Butanedione 3-Buten-2-one Butyrophenone D-Carvone

Chloroacetone Coumarin Cyclohexanone cis-Dibenzoylethylene trans-Dibenzoylethylene Dibenzoylmethane 9,10-Dihydro-9-oxoanthracene 1,5-Diphenyl-1,5-pentanedione 1,5-Diphenylthiocarbazone Flavanone

Fluorescein Fructose

B, pH 9.3 C D⫹McIlvaine buffer, pH 4.9 D⫹McIlvaine buffer, pH 7.2 D⫹McIlvaine buffer, pH 1.3

⫺1.52 ⫺2.46 ⫺1.33 ⫺1.58 ⫺1.08

0.1 N H2SO4⫹75% MeOH D⫹McIlvaine buffer, pH 1.3 D⫹McIlvaine buffer, pH 4.9 D⫹McIlvaine buffer, pH 1.3 D⫹McIlvaine buffer, pH 8.6 D⫹McIlvaine buffer, pH 1.3 D⫹McIlvaine buffer, pH 8.6 Buffer, pH 2.6 Buffer, pH 5.3 and pH 7.6 Buffer, pH 9.7 0.1 M LiCl 0.1 M HCl 0.1 M KCl 0.1 M NH4Cl⫹50% EtOH

⫺0.96 ⫺0.27 ⫺0.50 ⫺0.90 ⫺1.49 ⫺0.94 ⫺1.36 ⫺1.60 ⫺1.68 ⫺1.72 ⫺0.29 ⫺0.84 ⫺1.42 ⫺1.55

0.1 M Et4NI⫹80% EtOH 0.1 M LiCl McIlvaine buffer, pH 2.0 McIlvaine buffer, pH 5.0 C D, pH 1 D, pH 11 D, pH 1 D, pH 11 D, pH 1.3 D, pH 11.3 D, pH 2.0 A D, pH 7.0 Acetate buffer⫹Me4NOH⫹50% 2-PrOH, pH 6.1 Acetate buffer⫹Me4NOH⫹50% 2-PrOH, pH 9.6 Acetate buffer, pH 2.0 Phthalate buffer, pH 5.0 Borate buffer, pH 10.1 0.02 M LiCl

⫺1.71 ⫺1.18 ⫺0.95 ⫺1.11, ⫺1.44 ⫺2.45 ⫺0.30 ⫺0.62, ⫺1.65 ⫺0.12 ⫺0.57, ⫺1.52 ⫺0.59 ⫺1.30, ⫺1.62 ⫺0.93 ⫺2.10 ⫺0.6 ⫺1.30 ⫺1.51 ⫺0.50 ⫺0.65 ⫺1.18, ⫺1.44 ⫺1.76

short standard long

DEAN #37261

LEFT

(McGHP)

8.150

INTERACTIVE

top of rh base of rh

SECTION 8

TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C (Continued) Compound

Solvent system

cap height base of text

E1/2

Ketones (continued) Girard derivatives of aliphatic ketones

pH 8.2

⫺1.52

o-Hydroxyacetophenone p-Hydroxyacetophenone

D, pH 5 D, pH 5

⫺1.36 ⫺1.46

1,2,3-Indantrione (ninhydrin)

Britton-Robinson buffer, pH 2.5 Britton-Robinson buffer, pH 4.5 Britton-Robinson buffer, pH 6.8 Britton-Robinson buffer, pH 9.2 C Phosphate buffer⫹citrate buffer, pH 2.9 Phosphate buffer⫹citrate buffer, pH 4.3 Phosphate buffer⫹citrate buffer, pH 5.4

␣-Ionone Isatin

⫺0.67, ⫺0.83 ⫺0.73, ⫺1.01 ⫺0.10, ⫺0.90, ⫺1.20 ⫺1.35 ⫺1.59, ⫺2.08 ⫺0.3, ⫺0.5 ⫺0.3, ⫺0.5, ⫺0.8 ⫺0.8 ⫺0.64 ⫺1.28 ⫺1.01 ⫺1.60

4-Methyl-3,5-heptadien-2-one 4-Methyl-2,6-heptanedione 4-Methyl-3-penten-2-one

A A D⫹McIlvaine buffer, pH 1.3 D⫹McIlvaine buffer, pH 11.3

4-Phenyl-3-buten-2-one

D, pH 1.3 D, pH 8.6 0.1 M Bu4NI⫹50% dioxane pH 4.2 pH 9.7 C

⫺0.72 ⫺1.27 ⫺0.20 ⫺1.1, ⫺1.5 ⫺1.2, ⫺1.4 ⫺1.74

Quinalizarin

Phosphate buffer⫹1% EtOH, pH 8.0

⫺0.56

Testosterone

D⫹Britton-Robinson buffer, pH 2.6 D⫹Britton-Robinson buffer, pH 5.8 D⫹Britton-Robinson buffer, pH 8.8

⫺1.20

Phthalide Phthalimide Pulegone

⫺1.40 ⫺1.53, ⫺1.79

Quinones Acetate buffer⫹40% dioxane, pH 5.6 Phosphate buffer⫹40% dioxane, pH 7.9

⫺0.51

o-Benzoquinone

Britton-Robinson buffer, pH 7.0 Britton-Robinson buffer, pH 9.0

⫹0.20 ⫹0.08

2,3-Dimethylnaphthoquinone

D, pH 5.4

⫺0.22

1,2-Naphthoquinone

Phosphate buffer, pH 5.0 Phosphate buffer, pH 7.0 Britton-Robinson buffer, pH 7.0 Britton-Robinson buffer, pH 9.0

⫺0.03 ⫺0.13 ⫺0.07 ⫺0.19

Anthraquinone

1,4-Naphthoquinone

⫺0.71

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.151

TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C (Continued) Compound

Solvent system

E1/2

Acetic acid Acrylic acid Adenosine-5⬘-phosphoric acid 4-Aminobenzenesulfonic acid 3-Aminobenzoic acid Anthranilic acid Ascorbic acid

A pH 5.6 HClO4⫹KClO4 , pH 2.2 0.05 M Me4NI pH 5.6 pH 5.6 Britton-Robinson buffer, pH 3.4 Britton-Robinson buffer, pH 7.0

⫺2.3 ⫺0.85 ⫺1.13 ⫺1.58 ⫺0.67 ⫺0.67 ⫹0.17 ⫺0.06

Barbituric acid Benzoic acid Benzoylformic acid

Borate buffer, pH 9.3 A Britton-Robinson buffer, pH 2.2 Britton-Robinson buffer, pH 5.5 Britton-Robinson buffer, pH 7.2 Britton-Robinson buffer, pH 9.2 pH 1.1 pH 2.0

⫺0.04 ⫺2.1 ⫺0.48 ⫺0.85, ⫺1.26 ⫺0.98, ⫺1.25 ⫺1.25 ⫺0.54 ⫺0.39

top of rh base of rh cap height base of text

Acids

Bromoacetic acid 2-Bromopropionic acid

⫺1.94

Crotonic acid

C

Dibromoacetic acid Dichloroacetic acid 5,5-Diethylbarbituric acid

pH 1.1 pH 8.2 Borate buffer, pH 9.3

Flavanol

D, pH 5.6 D, pH 7.7

⫺1.25 ⫺1.40

Folic acid Formic acid Fumaric acid

Britton-Robinson buffer, pH 4.6 0.1 M KCl HCl⫹KCl, pH 2.6 Acetate buffer, pH 4.0 Acetate buffer, pH 5.9

⫺0.73 ⫺1.66 ⫺0.83 ⫺0.93 ⫺1.20

2,4-Hexadienedioic acid

Acetate buffer, pH 4.5

⫺0.97

Iodoacetic acid

pH 1

⫺0.16

Maleic acid

Britton-Robinson buffer, pH 2.0 Britton-Robinson buffer, pH 4.0 Britton-Robinson buffer, pH 6.0 Britton-Robinson buffer, pH 10.0

Mercaptoacetic acid Methacrylic acid

B, pH 6.8 D⫹0.1 M LiCl

Nitrobenzoic acids

Buffer⫹10% EtOH, pH 2.0

Oxalic acid 2-Oxo-1,5-pentanedioic acid

B, pH 5.4– 6.1 HCl⫹KCl, pH 1.8 Ammonia buffer, pH 8.2 Britton-Robinson buffer, pH 5.6 Britton-Robinson buffer, pH 6.8 Britton-Robinson buffer, pH 9.7

2-Oxopropionic acid

Phenolphthalein

Picric acid

Phthalate buffer, pH 2.5 Phthalate buffer, pH 4.7 D, pH 9.6 pH 4.2 pH 11.7

⫺0.03, ⫺0.59 ⫺1.57 0.00

⫺0.70 ⫺0.97 ⫺1.11, ⫺1.30 ⫺1.51 ⫺0.38 ⫺1.69 ⫺0.2, ⫺0.7 ⫺1.80 ⫺0.59 ⫺1.30 ⫺1.17 ⫺1.22, ⫺1.53 ⫺1.51 ⫺0.67 ⫺0.80 ⫺0.98, ⫺1.35 ⫺0.34 ⫺0.36, ⫺0.56, ⫺0.96

short standard long

DEAN #37261

LEFT

(McGHP)

8.152

INTERACTIVE

top of rh base of rh

SECTION 8

TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C (Continued) Compound

Solvent system

cap height base of text

E1/2

Acids (continued) 1,2,3-Propenetricarboxylic acid Trichloroacetic acid 3,4,5-Trihydroxybenzoic acid p-Aminophenol

pH 7.0 Ammonia buffer, pH 8.2 Phosphate buffer, pH 10.4 Phosphate buffer, pH 2.9 Phosphate buffer, pH 8.8 Britton-Robinson buffer, pH 6.3 Britton-Robinson buffer, pH 8.6 Britton-Robinson buffer, pH 12.0

⫺2.1 ⫺0.84, ⫺1.57 ⫺0.9, ⫺1.6 ⫹0.50 ⫹0.1 ⫹0.14 ⫺0.04 ⫺0.16

o-Chlorophenol m-Chlorophenol p-Chlorophenol o-Cresol m-Cresol p-Cresol

pH 5.6 pH 5.6 pH 5.6 pH 5.6 pH 5.6 pH 5.6

⫺0.63 ⫺0.73 ⫺0.65 ⫺0.56 ⫺0.61 ⫺0.54

1,2-Dihydroxybenzene 1,3-Dihydroxybenzene 1,4-Dihydroxybenzene

pH 5.6 pH 5.6 pH 5.6

⫺0.35 ⫺0.61 ⫺0.23

o-Methoxyphenol m-Methoxyphenol p-Methoxyphenol

pH 5.6 pH 5.6 pH 5.6

⫺0.46 ⫺0.62 ⫺0.41

1-Naphthol 2-Naphthol

A A

⫺0.74 ⫺0.82

1,2,3-Trihydroxybenzene

Britton-Robinson buffer, pH 3.1 Britton-Robinson buffer, pH 6.5 Britton-Robinson buffer, pH 9.5

⫹0.35 ⫹0.10 ⫺0.10

Halogen compounds

1-Bromobutane Bromoethane Bromomethane 1-Bromonaphthalene (also 2-bromonaphthalene) 3-Bromo-1-propene p-Bromotoluene

A C C C C A

⫺1.98 ⫺2.32 ⫺2.27 ⫺2.08 ⫺1.63 ⫺1.55, ⫺1.60

C A

⫺1.29 ⫺1.72

Carbon tetrachloride Chlorobenzene Chloroform Chloromethane 3-Chloro-1-propene ␣-Chlorotoluene p-Chlorotoluene N-Chloro-p-toluenesulfonamide

C A C C C C A 0.5 M K2SO4

⫺0.78, ⫺1.71 ⫺2.07 ⫺1.63 ⫺2.23 ⫺1.91 ⫺1.81 ⫺1.76 ⫺0.13

9,10-Dibromoanthracene p-Dibromobenzene 1,2-Dibromobutane

A C D⫹1% Na2SO3

⫺1.15, ⫺1.47 ⫺2.10 ⫺1.45

Bromobenzene

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.153

TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C (Continued) Compound

Solvent system

top of rh base of rh cap height base of text

E1/2

Halogen compounds (continued) ⫺1.48 ⫺0.23, ⫺0.89 ⫺2.5 ⫺1.60 ⫺1.12, ⫺1.53

Dibromoethane meso-2,3-Dibromosuccinic acid Dichlorobenzenes Dichloromethane Diiodomethane

C Acetate buffer, pH 4.0 C C C

Hexabromobenzene Hexachlorobenzene

C C

⫺0.8, ⫺1.5 ⫺1.4, ⫺1.7

Iodobenzene Iodoethane Iodomethane

A C A C

⫺1.72 ⫺1.67 ⫺2.12 ⫺1.63

Tetrabromomethane Tetraidomethane Tribromomethane ␣,␣,␣-Trichlorotoluene

C C C C

⫺0.3, ⫺0.75, ⫺1.49 ⫺0.45, ⫺1.05, ⫺1.46 ⫺0.64, ⫺1.47 ⫺0.68, ⫺1.65, ⫺2.00

Nitro and nitroso compounds 1,2-Dinitrobenzene 1,3-Dinitrobenzene 1,4-Dinitrobenzene

Phthalate buffer, pH 2.5 Borate buffer, pH 9.2 Phthalate buffer, pH 2.5 Borate buffer, pH 9.2 Phthalate buffer, pH 2.5 Borate buffer, pH 9.2

Methyl nitrobenzoates

Buffer⫹10% EtOH, pH 2.0

p-Nitroacetophenone

Britton-Robinson buffer, pH 2.2 Britton-Robinson buffer, pH 10.0 0.03 M LiCl⫹0.02 M benzoic acid in EtOH Britton-Robinson buffer, pH 4.3 Britton-Robinson buffer, pH 7.2 Britton-Robinson buffer, pH 9.2 pH 2.0 Acetate buffer, pH 4.6 Buffer⫹10% EtOH, pH 2.0 Buffer⫹10% EtOH, pH 2.0 Britton-Robinson buffer, pH 7.0 HCl⫹KCl⫹8% EtOH, pH 0.5 Phthalate buffer, pH 2.5 Borate buffer, pH 9.2 Britton-Robinson buffer, pH 2.2 Britton-Robinson buffer, pH 4.5 Britton-Robinson buffer, pH 8.0 Britton-Robinson buffer⫹30% MeOH, pH 1.8 Britton-Robinson buffer⫹30% MeOH, pH 4.6

o-Nitroaniline m-Nitroaniline

p-Nitroaniline o-Nitroanisole p-Nitroanisole 1-Nitroanthraquinone Nitrobenzene

Nitrocresols

Nitroethane

⫺0.12, ⫺0.32, ⫺1.26 ⫺0.38, ⫺0.74 ⫺0.17, ⫺0.29 ⫺0.46, ⫺0.68 ⫺0.12, ⫺0.33 ⫺0.35, ⫺0.80 ⫺0.20 to ⫺0.25 ⫺0.68 to ⫺0.74 ⫺0.16, ⫺0.61, ⫺1.09 ⫺0.51, ⫺1.40, ⫺1.73 ⫺0.88 ⫺0.3, ⫺0.8 ⫺0.5 ⫺0.7 ⫺0.36 ⫺0.5 ⫺0.29, ⫺0.58 ⫺0.35, ⫺0.64 ⫺0.16 ⫺0.16, ⫺0.76 ⫺0.30 ⫺0.70 ⫺0.2 to ⫺0.3 ⫺0.4 to ⫺0.5 ⫺0.6 ⫺0.7 ⫺0.8

short standard long

DEAN #37261

LEFT

(McGHP)

8.154

INTERACTIVE

top of rh base of rh

SECTION 8

TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C (Continued) Compound

Solvent system

cap height base of text

E1/2

Nitro and nitroso compounds (continued) 2-Nitrohydroquinone

Nitromethane

o-Nitrophenol

m-Nitrophenol

p-Nitrophenol

1-Nitropropane

2-Nitropropane Nitrosobenzene 1-Nitroso-2-naphthol

N-Nitrosophenylhydroxylamine o-Nitrotoluene

Phosphate buffer⫹citrate buffer, pH 2.1 Phosphate buffer⫹citrate buffer, pH 5.2 Phosphate buffer⫹citrate buffer, pH 8.0 Britton-Robinson buffer⫹30% MeOH, pH 1.8 Britton-Robinson buffer⫹30% MeOH, pH 4.6 Britton-Robinson buffer⫹10% EtOH, pH 2.0 Britton-Robinson buffer⫹10% EtOH, pH 4.0 Britton-Robinson buffer⫹10% EtOH, pH 8.0 Britton-Robinson buffer⫹10% EtOH, pH 10.0 Britton-Robinson buffer⫹10% EtOH, pH 2.0 Britton-Robinson buffer⫹10% EtOH, pH 4.0 Britton-Robinson buffer⫹10% EtOH, pH 8.0 Britton-Robinson buffer⫹10% EtOH, pH 10.0 Britton-Robinson buffer⫹10% EtOH, pH 2.0 Britton-Robinson buffer⫹10% EtOH, pH 4.0 Britton-Robinson buffer⫹10% EtOH, pH 8.0 Britton-Robinson buffer⫹30% MeOH, pH 1.8 Britton-Robinson buffer⫹30% MeOH, pH 8.6 Britton-Robinson buffer⫹30% MeOH, pH 8.0 McIlvaine buffer, pH 2.1 McIlvaine buffer, pH 5.1 McIlvaine buffer, pH 6.0 McIlvaine buffer, pH 8.0 D⫹buffer, pH 4.0 D⫹buffer, pH 7.0 D⫹buffer, pH 9.0 pH 2.0 Phthalate buffer, pH 2.5 Phthalate buffer, pH 7.4

⫺0.2 ⫺0.4 ⫺0.5 ⫺0.8 ⫺0.85 ⫺0.23 ⫺0.4 ⫺0.65 ⫺0.80 ⫺0.37 ⫺0.40 ⫺0.64 ⫺0.76 ⫺0.35 ⫺0.50 ⫺0.82 ⫺0.73 ⫺0.88 ⫺0.95 ⫺0.53 ⫺0.81 ⫺0.03 ⫺0.14 ⫹0.02 ⫺0.20 ⫺0.31 ⫺0.84 ⫺0.35, ⫺0.66 ⫺0.60, ⫺1.06

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.155

TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C (Continued) Compound

Solvent system

top of rh base of rh cap height base of text

E1/2

Nitro and nitroso compounds (continued) m-Nitrotoluene (also p-nitrotoluene)

Phthalate buffer, pH 2.5 Phthalate buffer, pH 7.4

⫺0.30, ⫺0.53 ⫺0.58, ⫺1.06

Tetranitromethane 1,3,5-Trinitrobenzene

pH 12.0 Phthalate buffer, pH 4.1 Borate buffer, pH 9.2

⫺0.41 ⫺0.20, ⫺0.29, ⫺0.34 ⫺0.34, ⫺0.48, ⫺0.65

Heterocyclic compounds containing nitrogen Acridine

D, pH 8.3

⫺0.80, ⫺1.45 ⫺0.90

Cinchonine

B, pH 3

2-Furanmethanol

Britton-Robinson buffer, pH 2.0 Britton-Robinson buffer, pH 5.8

⫺0.96 ⫺1.38, ⫺1.70

2-Hydroxyphenazine 8-Hydroxyquinoline

Britton-Robinson buffer, pH 4.0 B, pH 5.0 Phosphate buffer, pH 8.0

⫺0.24 ⫺1.12 ⫺1.18, ⫺1.71

3-Methylpyridine 4-Methylpyridine

D⫹0.1 M LiCl D⫹0.1 M LiCl

⫺1.76 ⫺1.87

Phenazine

Phosphate buffer⫹citrate buffer, pH 7.0 Phosphate buffer⫹citrate buffer, pH 7.0 B, pH 4.1 B, pH 9.3 0.1 M HCl Britton-Robinson buffer, pH 6.1 pH 9.0 Citrate buffer, pH 3.6 Ammonia buffer, pH 9.2

⫺0.36

Pyridine Pyridine-2-carboxylic acid Pyridine-3-carboxylic acid Pyridine-4-carboxylic acid Pyrimidine Quinoline-8-carboxylic acid Quinoxaline

pH 9 Phosphate buffer⫹citrate buffer, pH 7.0

⫺1.75 ⫺1.10 ⫺1.48, ⫺1.94 ⫺1.08 ⫺1.14 ⫺1.39, ⫺1.68 ⫺0.92, ⫺1.24 ⫺1.54 ⫺1.11 ⫺0.66, ⫺1.52

Azo, hydrazine, hydroxylamine, and oxime compounds D, pH 4.0 D, pH 7.0 Buffer⫹20% EtOH, pH 6.3

⫺0.20 ⫺0.50 ⫺0.30

Benzoylhydrazine

Buffer, pH 2.0 Buffer, pH 5.6 Buffer, pH 8.2 0.13 M NaOH, pH 13.0

⫺0.88 ⫺1.08 ⫺1.67 ⫺0.30

Dimethylglyoxime

Ammonia buffer, pH 9.6

⫺1.63

Hydrazine Hydroxylamine

Britton-Robinson buffer, pH 9.3 Britton-Robinson buffer, pH 4.6 Britton-Robinson buffer, pH 9.2

⫺0.09 ⫺1.42 ⫺1.65

Azobenzene Azoxybenzene Benzoin 1-oxime

short standard long

DEAN #37261

LEFT

(McGHP)

8.156

INTERACTIVE

top of rh base of rh

SECTION 8

TABLE 8.31 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25⬚C (Continued) Compound

Solvent system

cap height base of text

E1/2

Azo, hydrazine, hydroxylamine, and oxime compounds (continued) Oxamide

Acetate buffer

⫺1.55

Phenylhydrazine

McIlvaine buffer, pH 2 0.13 M NaOH, pH 13.0 McIlvaine buffer⫹10% EtOH, pH 2 McIlvaine buffer⫹10 EtOH, pH 4– 10

⫹0.19 ⫺0.36 ⫺0.68 ⫺0.33 0.061 pH

Salicylaldoxime

Phosphate buffer, pH 5.4

⫺1.02

Thiosemicarbazide Thiourea

Borate buffer, pH 9.3 0.1 M sulfuric acid

⫺0.26 ⫹0.02

Phenylhydroxylamine

Indicators and dyestuffs Brilliant Green Indigo carmine Indigo disulfonate

HCl⫹KCl, pH 2.0 pH 2.5 pH 7.0

⫺0.2, ⫺0.5 ⫺0.24 ⫺0.37

Malachite Green G Metanil yellow

HCl⫹KCl, pH 2.0 Phosphate buffer⫹1% EtOH, pH 7.0 Britton-Robinson buffer, pH 4.9 Britton-Robinson buffer, pH 9.2 Phosphate buffer⫹1% EtOH, pH 7.0 Phosphate buffer⫹1% EtOH, pH 7.0 D, pH 7.6

⫺0.2, ⫺0.5 ⫺0.51

Britton-Robinson buffer, pH 2.0 Britton-Robinson buffer, pH 7.0

⫺0.21 ⫺0.57

Methylene blue Methylene green Methyl orange Morin Neutral red

⫺0.15 ⫺0.30 ⫺0.12 ⫺0.51 ⫺1.7

Peroxide Ethyl peroxide

0.02 M HCl

⫺0.2

short standard long

DEAN #37261

8.7

(McGHP)

RIGHT

INTERACTIVE

ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.157

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CONDUCTANCE

TABLE 8.32 Limiting Equivalent Ionic Conductances in Aqueous Solutions In 10⫺4 m 2 · S · equiv⫺1 or mho · cm2 · equiv⫺1. Temperature, ⬚C Ion Inorganic cations Ag⫹ Al 3⫹ Ba2⫹ Be2⫹ Ca2⫹ Cd2⫹ Ce3⫹ Co2⫹ Co(NH3 ) 63⫹ Co(ethylenediamine) 33⫹ Cr3⫹ Cs⫹ Cu2⫹ D⫹ (deuterium) Dy3⫹ Er3⫹ Eu3⫹ Fe2⫹ Fe3⫹ Gd3⫹ H⫹ Hg 22⫹ Hg2⫹ Ho3⫹ K⫹ La3⫹ Li⫹ Mg2⫹ Mn2⫹ NH ⫹4 N2 H 5⫹ (hydrazinium 1⫹) Na⫹ Nd3⫹ Ni2⫹ Pb2⫹ Pr3⫹ Ra2⫹ Rb⫹ Sc3⫹ Sm3⫹ Sr2⫹ Tl⫹ Tm3⫹ UO 22⫹ Y 3⫹ Yb 3⫹ Zn2⫹

0

18

33 29 33.6

54.5

30.8 28

51 45.1

28

45

44 28

68 45.3 213.7

54.3

28

45.3

224.1

315.8

40.3 35.0 19.1 28.5 27 40.3

64.6 59.2 33.4 46 44.5 64

25.85

43.5

28 37.5

45 60.5

33 43.5

56.6 67.5

31 43.3

51 66

28

45.0

25

61.9 61 63.9 45 59.5 54 70 53 100 74.7 67 77.3 56.6 65.7 66.0 67.9 53.5 69 67.4 350.1 68.7 63.6 66.3 73.5 69.6 38.69 53.06 53.5 73.7 59 50.11 69.6 50 71 69.6 66.8 77.8 64.7 68.5 59.46 74.9 65.5 32 62 65.2 52.8

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TABLE 8.32 Limiting Equivalent Ionic Conductances in Aqueous Solutions (Continued) Temperature, ⬚C Ion Inorganic anions Au(CN) ⫺2 Au(CN) ⫺4 B(C6 H5 )4⫺ Br ⫺ Br ⫺3 BrO ⫺3 Cl⫺ ClO ⫺2 ClO ⫺3 ClO ⫺4 CN⫺ CO 23⫹ Co(CN) 36⫺ CrO 24⫺ F⫺ Fe(CN)46⫺ Fe(CN) 36⫺ H2AsO4⫺ HCO⫺3 HF ⫺2 HPO 24⫺ H2PO4⫺ HS⫺ HSO⫺3 HSO ⫺4 H2SbO⫺4 I⫺ IO⫺3 IO⫺4 MnO⫺4 MoO24⫺ N⫺3 N(CN)⫺2 NO⫺2 NO⫺3 NH2 SO3⫺ (sulfamate) OCN⫺ (cyanate) OH⫺ PF⫺6 PO3F 2⫺ PO34⫺ P2O47⫺ P3O 93⫺ 5⫺ P3O 10 ReO⫺4 SCN⫺ (thiocyanate) SeCN⫺ SeO24⫺ SO23⫺

0

18

43.1

67.6

31.0 41.4

49.0 65.5

36 37.3

55.0 59.1

36

60.5

42

72 46.6

40 27

42.0 21.0

28 57

36

66.5 33.9 49 53

44 40.2

59 61.7

117.8

54.8 175.8

41.7

46.5 56.6 65

25

50 36 21 78.1 43 55.7 76.31 52 64.6 67.3 78 69.3 98.9 85 55.4 110.4 100.9 34 44.5 75 33 33 65 50 50 31 76.9 40.5 54.5 61.3 74.5 69.5 54.5 71.8 71.42 48.6 64.6 198 56.9 63.3 69.0 96 83.6 109 54.9 66.5 64.7 75.7 79.9

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TABLE 8.32 Limiting Equivalent Ionic Conductances in Aqueous Solutions (Continued) Temperature, ⬚C Ion SO24⫺ S2O23⫺ S2O24⫺ S2O26⫺ S2O 82⫺ WO24⫺

0 41

18 68.3

34

35

59

Organic cations Decylpyridinium⫹ Diethylammonium⫹ Dimethylammonium⫹ Dipropylammonium⫹ Dodecylammonium⫹ Ethylammonium⫹ Ethyltrimethylammonium⫹ Isobutylammonium⫹ Methylammonium⫹ Piperidinium⫹ Propylammonium⫹ Tetrabutylammonium⫹ Tetraethylammonium⫹ Tetramethylammonium⫹ Tetrapropylammonium⫹ Triethylsulfonium⫹ Trimethylammonium⫹ Trimethylsulfonium⫹ Tripropylammonium⫹ Organic anions Acetate⫺ Benzoate⫺ Bromoacetate⫺ Bromobenzoate⫺ Butanoate⫺ Chloroacetate⫺ m-Chlorobenzoate⫺ o-Chlorobenzoate⫺ Citrate(3⫺) Crotonate⫺ Cyanoacetate⫺ Cyclohexanecarboxylate⫺ Cyclopropane-1,3-dicarboxylate2⫺ Decylsulfonate⫺ Dichloroacetate⫺ Diethylbarbiturate(2⫺) Dihydrogencitrate⫺ Dimethylmalonate(2⫺) 3,5-Dinitrobenzoate⫺ Dodecylsulfonate⫺ Ethylmalonate⫺ Ethylsulfonate⫺

25 80.0 85.0 66.5 93 86 69.4 29.5 42.0 51.5 30.1 23.8 47.2 40.5 38.0 58.3 37.2 40.8 19.5 32.6 44.9 23.5 36.1 47.2 51.4 26.1

20

34

41 32.4 39.2 30 32.6 42.2 31 30.5 70.2 33.2 43.4 28.7 53.4 26 38.3 26.3 30 49.4 28.3 24 49.3 39.6

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TABLE 8.32 Limiting Equivalent Ionic Conductances in Aqueous Solutions (Continued) Temperature, ⬚C Ion

0

18

Fluoroacetate⫺ Fluorobenzoate⫺ Formate⫺ Fumarate(2⫺) Glutarate(2⫺) Hydrogenoxalate (1⫺) Iodoacetate⫺ Lactate(1⫺) Malate(2⫺) Malonate(1⫺) 3-Methylbutanoate⫺ Methylsulfonate⫺ Naphthylacetate⫺ 1,8-Octanedioate(2⫺) Octylsulfonate⫺ Oxalate(2⫺) Phenylacetate⫺ m-Phthalate(2⫺) o-Phthalate(2⫺) Picrate⫺ Propanoate⫺ Propylsulfonate⫺ Salicylate⫺ Succinate(2⫺) Tartrate(2⫺) Trichloroacetate⫺ Trimethylacetate⫺

47

55

25 44.4 33 54.6 61.8 52.6 40.2 40.6 38.8 58.8 63.5 32.7 48.8 28.4 36 29 74.11 30.6 54.7 52.3 30.37 35.8 37.1 36 58.8 59.6 36.6 31.9

TABLE 8.33 Standard Solutions for Calibrating Conductivity Vessels The values of conductivity ␬ are corrected for the conductivity of the water used. The cell constant ␪ of a conductivity cell can be obtained from the equation

␪⫽

␬RRsolv Rsolv ⫺ R

where R is the resistance measured when the cell is filled with a solution of the composition stated in the table below, and Rsolv is the resistance when the cell is filled with solvent at the same temperature. Conductivity in ohm⫺1 · cm⫺1 at Grams KCl per Kilogram Solution (in vacuo)

0⬚C

18⬚C

25⬚C

71.135 2 7.419 13 0.745 263*

0.065 144 0.007 1344 0.000 773 26

0.097 790 0.011 1612 0.001 219 92

0.111 287 0.012 8497 0.001 408 08

* Virtually 0.0100 M. From the data of Jones and Bradshaw, J. Am. Chem. Soc., 55, 1780 (1933). The original data have been converted from (int. ohm)⫺1 cm⫺1.

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TABLE 8.34 Electrical Conductivity of Various Pure Liquids

Liquid Acetaldehyde Acetamide Acetic acid Acetic anhydride Acetone Acetonitrile Acetophenone Acetyl bromide Acetyl chloride Alizarin Allyl alcohol Ammonia Aniline Anthracene Arsenic tribromide Arsenic trichloride Benzaldehyde Benzene Benzoic acid Benzonitrile Benzyl alcohol Benzylamine Benzyl benzoate Bromine Bromobenzene Bromoform iso-Butyl alcohol

Temp. ⬚C 15 100 0 25 0 25 18 25 20 25 25 25 233 25 ⫺79 25 230 35 25 25 ··· 125 25 25 25 25 17.2 25 25 25

Capronitrile Carbon disulfide Carbon tetrachloride Chlorine Chloroacetic acid m-Chloroaniline Chloroform Chlorohydrin m-Cresol Cyanogen Cymene

25 1 18 ⫺70 60 25 25 25 25 ··· 25

Dichloroacetic acid Dichlorohydrin Diethylamine Diethyl carbonate Diethyl oxalate Diethyl sulfate Dimethyl sulfate

25 25 ⫺33.5 25 25 25 0

mhos/cm or ohm⫺1 · cm⫺1 1.7 ⫻ 10⫺6 ⬍4.3 ⫻ 10⫺5 5 ⫻ 10⫺9 1.12 ⫻ 10⫺8 1 ⫻ 10⫺6 4.8 ⫻ 10⫺7 2 ⫻ 10⫺8 6 ⫻ 10⫺8 7 ⫻ 10⫺6 6 ⫻ 10⫺9 2.4 ⫻ 10⫺6 4 ⫻ 10⫺7 1.45 ⫻ 10⫺6 (?) 7 ⫻ 10⫺6 1.3 ⫻ 10⫺7 2.4 ⫻ 10⫺8 3 ⫻ 10⫺10 1.5 ⫻ 10⫺6 1.2 ⫻ 10⫺6 1.5 ⫻ 10⫺7 7.6 ⫻ 10⫺8 3 ⫻ 10⫺9 5 ⫻ 10⫺8 1.8 ⫻ 10⫺6 ⬍1.7 ⫻ 10⫺8 ⬍1 ⫻ 10⫺9 1.3 ⫻ 10⫺13 ⬍2 ⫻ 10⫺11 ⬍2 ⫻ 10⫺8 8 ⫻ 10⫺8 3.7 ⫻ 10⫺6 7.8 ⫻ 10⫺18 4 ⫻ 10⫺18 ⬍1 ⫻ 10⫺16 1.4 ⫻ 10⫺6 5 ⫻ 10⫺8 ⬍2 ⫻ 10⫺8 5 ⫻ 10⫺7 ⬍1.7 ⫻ 10⫺8 ⬍7 ⫻ 10⫺9 ⬍2 ⫻ 10⫺8 7 1.2 2.2 1.7 7.6 2.6 1.6

⫻ 10⫺8 ⫻ 10⫺5 ⫻ 10⫺9 ⫻ 10⫺8 ⫻ 10⫺7 ⫻ 10⫺7 ⫻ 10⫺7

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Liquid

Temp. ⬚C

mhos/cm or ohm⫺1 · cm⫺1 3.4 ⫻ 10⫺8 ⬍1 ⫻ 10⫺9 4 ⫻ 10⫺8 1.35 ⫻ 10⫺9 4 ⫻ 10⫺7 ⬍1 ⫻ 10⫺9 ⬍2 ⫻ 10⫺8 ⬍2 ⫻ 10⫺10 3 ⫻ 10⫺8 ⬍4 ⫻ 10⫺13 ⬍1.7 ⫻ 10⫺8 ⬍2 ⫻ 10⫺8 1.26 ⫻ 10⫺7 5.3 ⫻ 10⫺7 1.2 ⫻ 10⫺6 ⬍1.7 ⫻ 10⫺8

Epichlorohydrin Ethyl acetate Ethyl acetoacetate Ethyl alcohol Ethylamine Ethyl benzoate Ethyl bromide Ethylene bromide Ethylene chloride Ethyl ether Ethylidene chloride Ethyl iodide Ethyl isothiocyanate Ethyl nitrate Ethyl thiocyanate Eugenol

25 25 25 25 0 25 25 19 25 25 25 25 25 25 25 25

Formamide Formic acid Furfural

25 18 25 25

4 5.6 6.4 1.5

Gallium Glycerol Glycol Guaiacol

30 25 25 25

36,800 6.4 ⫻ 10⫺8 3 ⫻ 10⫺7 2.8 ⫻ 10⫺7

··· 18 ⫺80 ⫺96 0 B.P. B.P.

⬍1 ⫻ 10⫺13 ⬍1 ⫻ 10⫺18 8 ⫻ 10⫺9 1 ⫻ 10⫺8 3.3 ⫻ 10⫺6 2 ⫻ 10⫺7 1 ⫻ 10⫺11

110

1.3 ⫻ 10⫺10

Kerosene

25

⬍1.7 ⫻ 10⫺8

Mercury Methyl acetate Methyl alcohol Methyl ethyl ketone Methyl iodide Methyl nitrate Methyl thiocyanate

0 25 18 25 25 25 25

10,629.6 3.4 ⫻ 10⫺6 4.4 ⫻ 10⫺7 1 ⫻ 10⫺7 ⬍2 ⫻ 10⫺8 4.5 ⫻ 10⫺6 1.5 ⫻ 10⫺6

Naphthalene Nitrobenzene Nitromethane o- or m-Nitrotoluene Nonane

82 0 18 25 25

4 ⫻ 10⫺10 5 ⫻ 10⫺9 6 ⫻ 10⫺7 ⬍2 ⫻ 10⫺7 ⬍1.7 ⫻ 10⫺8

Heptane Hexane Hydrogen Hydrogen Hydrogen Hydrogen Hydrogen

bromide chloride cyanide iodide sulfide

Iodine

⫻ 10⫺6 ⫻ 10⫺5 ⫻ 10⫺5 ⫻ 10⫺6

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TABLE 8.34 Electrical Conductivity of Various Pure Liquids (Continued)

Liquid

Temp. ⬚C

Oleic acid

15

Pentane Petroleum Phenetole Phenol Phenyl isothiocyanate Phosgene Phosphorus Phosphorus oxychloride Pinene Piperidine Propionaldehyde Propionic acid Propionitrile n-Propyl alcohol iso-Propyl alcohol n-Propyl bromide Pyridine

19.5 ··· 25 25 25 25 25 25 23 25 25 25 25 18 25 25 25 18

Quinoline

25

mhos/cm or ohm⫺1 · cm⫺1 ⬍2 ⫻ 10⫺10 ⬍2 ⫻ 10⫺10 3 ⫻ 10⫺13 ⬍1.7 ⫻ 10⫺8 ⬍1.7 ⫻ 10⫺8 1.4 ⫻ 10⫺6 7 ⫻ 10⫺9 4 ⫻ 10⫺7 2.2 ⫻ 10⫺6 ⬍2 ⫻ 10⫺10 ⬍2 ⫻ 10⫺7 8.5 ⫻ 10⫺7 ⬍1 ⫻ 10⫺9 ⬍1 ⫻ 10⫺7 5 ⫻ 10⫺8 2 ⫻ 10⫺8 3.5 ⫻ 10⫺6 ⬍2 ⫻ 10⫺8 5.3 ⫻ 10⫺8 2.2 ⫻ 10⫺8

Liquid

Temp. ⬚C

mhos/cm or ohm⫺1 · cm⫺1

25 80 25

1.6 ⫻ 10⫺7 ⬍4 ⫻ 10⫺13 2 ⫻ 10⫺6

115 130 440 35 25 25

1 ⫻ 10⫺12 5 ⫻ 10⫺12 1.2 ⫻ 10⫺7 1.5 ⫻ 10⫺8 1 ⫻ 10⫺2 3 ⫻ 10⫺8

··· 25 100 25 ⫺33.5 ···

⬍1 ⫻ 10⫺14 ⬍2 ⫻ 10⫺6 6.2 ⫻ 10⫺8 3 ⫻ 10⫺9 2.2 ⫻ 10⫺10 2 ⫻ 10⫺13

iso-Valeric acid

80

⬍4 ⫻ 10⫺13

Water

18

4 ⫻ 10⫺8

Xylene

···

⬍1 ⫻ 10⫺15

Salicylaldehyde Stearic acid Sulfonyl chloride, SOCl2 Sulfur

Sulfur dioxide Sulfuric acid Sulfuryl chloride, SO2Cl2 Toluene o-Toluidine p-Toluidine Trichloroacetic acid Trimethylamine Turpentine

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TABLE 8.35 Equivalent Conductivities of Electrolytes in Aqueous Solutions at 18⬚C The unit of ⌳ in the table is ⍀ ⫺1 · cm⫺2 · equiv⫺1. The entities to which the equivalent relates are given in the first column. Concentration, N 0.005

0.01

20.0 110.0 108.4 124 105.0 124 115 76.8 80.4 106.8 112.3 105.3 213

14.3 107.8 102.9 119 93.8 119 110 60.6 77.1 102.7 106.7 101.0 207

79.6 112.0 108.5

75.0 106.7 103.0 233 86.3 86.5 91 76.7 100 79.7

104.3

97.7 137.4 85.5 88.4

54 54 99.3

0.1

0.5

1.0

2.0

3.0

4.0

5.0

6.48 99.5

4.60 94.3

2.01 77.8

1.32 67.8

56.0

0.54 48.2

42.1

0.29 37.2

65.0

56.2

44.2

34.7

27.2

60.3

52.3 29.8

23.4

103 108 94

97 88

65.7

60.2

43.8

34.3

96.0 86.8 191

90.8 78.9 180

77.3 56.6

70.1 48.4

71.9 103.4 99.5 226 77.4 76.3 83 65.6 96 70.3 122.1 45.8

60.3 93.3 88.4

54.0 88.2 82.5

1.66 36.3 74.9 65.7

0.98 26.3 67.5 55.9

58.3 43.5

49.7 35.5

42.4 26.0

35.6 21.5

53.2 59 40.1 86.4 49.6

44.6 50 31.0 80.8 42.2 99.0

25.3 30.8 18.3 63.9 28.7

18.3 22.4 15.4 54.5 23.6

12.5 14.4 12.3 41.0 17.7

9.1 9.9 9.7 31.4 14.0

6.8 7.1 8.0 23.7 11.0

5.3 5.4 17.6 8.35

20.2 7.3 51.5 68.6

13.6 5.4 45.3 56.8

5.6

4.2

3.3

22.0 82.3

42.9 16.1 75.0

8.1

42.5 95.6

40.3 44.8

35.4 35.2

30.5

26.4

0.46

0.26

0.18

0.11

29

INTERACTIVE

41 113.2 116.3 132 121.1 131 123 107.2 85.0 113.6 115.6 111.7 216

0.05

RIGHT

Acetic acid AgNO3 1⁄2 Ag SO 2 4 1⁄3 AlBr (25⬚) 3 1⁄3 AlCl 3 1⁄3 AlI (25⬚) 3 1⁄3 Al(NO ) (25⬚) 3 3 1⁄6 Al (SO ) (25⬚) 2 4 3 1⁄2 Ba(OAc) 2 1⁄2 Ba(BrO ) (25⬚) 3 2 1⁄2 BaCl 2 1⁄2 Ba(NO ) 3 2 1⁄2 Ba(OH) 2 Butyric acid 1⁄2 Ca(OAc) 2 1⁄2 CaCl 2 1⁄2 Ca(NO ) 3 2 1⁄2 Ca(OH) 2 1⁄2 CaSO 4 1⁄2 CdBr 2 1⁄2 CdCl 2 1⁄2CdI 2 1⁄2Cd(NO ) 3 2 1⁄2CdSO 4 1⁄3 CeCl (25⬚) 3 1⁄6 Ce (C O ) (25⬚) 2 2 4 3 Chloroacetic acid (25⬚) Citric acid 1⁄2CoCl 2 1⁄3CrCl 3

0.001

(McGHP)

Electrolyte

8.163

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DEAN #37261

TABLE 8.35 Equivalent Conductivities of Electrolytes in Aqueous Solutions at 18⬚C (Continued) Concentration, N Electrolyte

0.005

0.01

201 130.7 55.7

195 127.5 50.6

193 125.2 47.2

107.9 98.5

97.1 81.0

93.7 71.7

131 82 125.6 308.2 13.5 401 377 413

0.05 191 34.9

0.5

1.0

2.0

3.0

186 113.5 28.4

104.3

100.3

95.7

85.1

67.5 30.5 119

56.8 25.6 82

41.2 45.4 19.7 44.6

66.5 30.8

52.9 25.8 5.18

37.6 19.5 3.68

125

120

103

78.2 43.8 207.5 93

75

70

54

44.5

230.0

187.0

103.4

80.4

387 373

373 370

272 360

406 90

402 60 323.9 368 255 390 308

98.3 129.4 109.9

95.7 126.4 106.9 109.9

94.0 124.4 104.7 103

357 377 253 1.85 87.7 117.8 97.3 87.8

370 225 1.23 53.9 83.8 114.2 93.0 80.8

5.0

31.5 35.3 16.5 26.5

24.5 27.8

19.1 21.4

16.3

9.6

28.1 15.37 2.93

20.5

15.9

306

282

243

214

327 317 358 27.0 322 175 324

301 292

247

215 207

205

198

37.0 71.6 105.4

28.7 63.4 102.5

25.7 297 141 310 66

255 106

24.2 215 87 220 53.1

2.39

179 152.2

24.0 179 71 156 51.3

166.8 19.8 50.0 98.0

14.4 40.7 93.3

1.92

135.0 10.1 31.4 87.9

INTERACTIVE

332.8 371 279 394 330

392 35.9

356 156 351 343 386 31.3 347 253 350

4.0

LEFT

343.3 375 318 399 361

83.7 53.6

0.1

(McGHP)

⁄ CrO3(H2CrO 4 ) (25⬚) CsCl 1⁄2Cu(OAc) (25⬚) 2 1⁄2CuCl 2 1⁄2Cu(NO ) (15⬚) 3 2 1⁄2CuSO 4 Dichloroacetic acid (25⬚) 1⁄2FeCl (25⬚) 2 1⁄3FeCl 3 1⁄2FeSO 4 Formic acid H3 AsO4 (1 M) (25⬚) H3BO3 HBr HBrO3 (25⬚) HCl HClO3 HClO4 (25⬚) HF HI HIO3 HNO3 H3PO4 (1 M) HSCN (25⬚) 1⁄2 H SO 2 4 1⁄2 HgCl 2 1⁄3 InBr 3 KOAc KBr KBrO3 1⁄3 K citrate 3 12

0.001

24.5

8.164

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base of DF

127.3 116.9 137.9

124.4 113.6 134.2

122.4 111.6 131.5

115.8 103.7 121.6

112.0 99.2 115.2

133.0 122.4

121.6 116.7

115.5 112.5

100.7 100.8

106.2 150.7 146.1 112.2 103.7

97.7

134.8 110.1 99.9

107.7

97.9

89.3

83.8

120.5 230 121.3

98.0 123.4 91.2 118.5 126.5 118.2 228 118.5

118.6 126.9 137.0

115.8 120.3 127.5

113.9 115.8 121.8

53.5

39

90.7 117.3 84.1 106.7 109.9 219 106.4 107.7 101.9 106.2 86.1 25.7 18.1

93.9 100.6

92.1 98.6

65.3

62.9

61.2

55.3

104.3 94.9 99.1 72.1 21.5 13.2 51.3 84.4 82.4 88.6 59.1 51.5

88.9

104.2 77.8 80.4 86.4 85.4 82.6

99.7 70.7 73.7 79.5

65.0

55.6

72.0

59.9

76.0

63.4

56.5

86.5

78.9

92.5 21.0 60.018 106.2

91.7 18.4 45.818 103.6

86.4 15.2

80.7

101.3

96.4

89.2 197

80.5 184

69.4

61.3 140.6

135.6 91.6 71.6

119.7 86.8

108.3 74.6

97.2

95.7 78.5 65.4

54.0

39.1

28.5

19.9

37.7 73.9 70.7

28.9 67.2 63.4

18.2 57.7 53.1

11.9 45.3

75.3 39.0

69.2 31.2

61.0 21.4

14.6

49.2

42.9

51.7

46.5

69.3

89.0

81.2

105.8 86.1

7.2 44.2

INTERACTIVE

96.5 103.4

87.9 86.1 92.2 64.2

85.6 114.0 79.7 98.1 113 104.8 213 97.4

92.0

RIGHT

107.1 128.2 96.0 124.9 133.3 123.6 234 125.1

108.9

100.8 125.3 93.2 121.2

104.3

98.3

(McGHP)

108.9 163.1 167.2 115.3 119.3

94.1 94.9 100.5 98.2 94.0

102.4 85.3

DEAN #37261

KCl KClO3 KClO4 (25⬚) KCN (15⬚) 1⁄2 K CO 2 3 1⁄2 K C O 2 2 4 1⁄2 K CrO 2 4 1⁄2 K Cr O 2 2 7 KF 1⁄3 K [Fe(CN) ] 3 6 1⁄4 K [Fe(CN) ] 4 6 KHCO3 (25⬚) KH phthalate KHS KHSO4 KH2 PO4 (1 M) (25⬚) KI KIO3 KIO4 (25⬚) KMnO4 (25⬚) KNO3 KOH KReO4 (25⬚) 1⁄2 K S 2 KSCN 1⁄2K SO 2 4 1⁄2 LaCl (25⬚) 3 1⁄3 La(NO ) 3 3 1⁄6 La (SO ) 2 4 3 Lactic acid LiOAc LiBr LiCl LiClO4 (25⬚) 1⁄2 Li CO 2 3 LiI LiIO3

33.3

8.165

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DEAN #37261

TABLE 8.35 Equivalent Conductivities of Electrolytes in Aqueous Solutions at 18⬚C (Continued) Concentration, N Electrolyte

0.005

0.01

0.05

0.1

0.5

1.0

92.9

90.3

88.6

82.7

79.2

96.4 106.4 102.6 99.8

101.3 97.7 84.5

86.9 98.1 94.7 76.2

74.7 88.5 85.3 56.9

68.2 83.4 80.5 49.7 86.0

13.2 92.9 124.3

9.6 91.4 122.1

4.6 84.9 115.2

3.3

118.0

118.0 110.0

68.0 149.0 50.5 69.6 67.0 35.4 68.5 27.6 1.35 60.5 101.4 74.5 106.0 94.5 94.0 79.5 49.4 84.6 61.8

60.8 134.5 41.3 61.5 59.0 28.9 61.0 24.4 0.89 54.7 97.0 65.7 103.1 88.8 89.9 73.0 41.2 78.1 54.5

42.9 92.1 55.3 100.0 85.1 84.7 65.0 29.8 69.1 44.1

80.9 71.7 54.5 66.4

74.3 65.0 45.5 57.7

64.8 55.1 34.5 46.6

56.5 46.0 27.2 38.3

49.4 38.8

60.0

51.9

61.4

53.7

43.1

34.8

28.2

33.5

28.0

25.4 97.5

89.9

78.6

69.9

62.2

28.0 127.3 124.5 75.2

87.8

77.6 103.8 111.725 102.5

75.8 102.0 109.625 96.2

103 85.2 129.6 90.5 65.8 39.4 121.2

83.5 120.0 88.4 54.0 64.4 38.2 119.2

64.2 99.1 69.3 95.7 102.425 80.3 98.3 77.0 97.0 80.6 57.8 34.6 112.8

65.3 92.0 98.425 72.9 82.5 94.9 73.1 88.2 76.0 44.0 54.1 32.5 108.8

4.0

34.9 95.7 23.3 43.3 39.8 17.3 38.8 14.0 0.36 34.0 88.2 47.9

27.3

79.2 21.5

5.0

18.1 35.0

13.9 28.0

12.9 30.2 10.5

9.3 23.0 7.3 0.20

26.5 85.0 42.2 91.4 71.9 74.0 55.2 15.3 53.0

80.7 84.5 47.6 10.5

42.7

31.1

INTERACTIVE

88.6 93.5 58.4 67.9 41.1 124.2

116.5 70.2

50.3 113.5 30.7 52.3 47.0 23.0 48.5 18.3

3.0

LEFT

80.3 106.5 114.925 112

120.0 72.4

110.7 90.1 115.0 106.6 104.3 89.0 61.1 96.0

2.0

(McGHP)

LiNO3 LiOH 1⁄2 Li SO 2 4 1⁄2 MgCl 2 1⁄2 Mg(NO ) 3 2 1⁄2 MgSO 4 1⁄2 MnCl 2 1⁄2 MnSO 4 NH3(aq) NH4OAc NH4Cl NH4F NH4I NH4NO3 NH4SCN 1⁄2 (NH ) SO 4 2 4 NaOAc NaBr NaBrO3 Na n-butyrate (25⬚) NaCl NaClO4 1⁄2 Na CO 2 3 1⁄2 Na CrO 2 4 1⁄2 Na Cr O (25⬚) 2 2 7 NaF 1⁄4 Na [Fe(CN) ] (25⬚) 4 6 Na formate NaHCO3 (25⬚) 1⁄3 Na HPO 2 4 NaH2 PO4 1⁄4 Na H P O 2 2 2 7 NaI

0.001

8.166

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short standard

base of DF

72.6 113 113.8

70.9 110 110.5

102.9 208 78.6 125 83.5

100.1 203 75.7 122 80.9

98.2 200 73.7 119 79.1

144 106.7 120 116.1 96.3 180.7 116.1

139 100.8 81.5 109.2 79.5

130.3

64.4

60.5

101.3

95.7

91.4 190 66.3 91

87.2 183 61.8

108.6

136 96.8 74.8 104.8 70.8 158.2 103.5

124 83.9 64.3 92.2 51.0 132.9 86.3

116 78.4 60.4 85.8 43.8 116.9 77.3

127.4

125.3

117.8

113.9 220.6

105.4 99.0

94.4 87.3

128.2 113.3 124.7 127.4

123.7 108.2 121.1 118.4

120.2 105.4 118.4 112.3

97.4 107.9 92.7

26.10 106.5 129 83 107 120 98.4

12.31 63.2 122 77 101 114 82.1

9.17 49.2 118 73 98 111 73.2

5.43 27.6 109 58 87 100 53.0

90.2 80.9

92.6 101.2 83.1 4.74 22.2

117.0 74.3 88 59.7

104.3 68.9 72 50.8

85.0 59.8 51 40.0

71.0 50.9 38 33.5

19.3

15.1

61.0

25.1 59.4 42.0 1.00 101.9 192.0 121.7 68.5 52.1 7.03 54.0

31.0 0.54 97.1 170.0 66.9 58.7 38.0 4.58 44.3

92.7 148.3 47.9 49.9 29.3 3.32 36.3

78.8

71.5

62.7

273 3.75 14.4

207 3.22 11.6

30.4 75.9 53.2 1.57 204.8 216.8 75.7 62.7

127

53.6 46.0 108.0

39.7 39.0 69.0

59.0 43.7 27

47.2 19

0.20 87.2 32.7 42.2 29.3 2.48 29.8

16.4 1.83

79

44

19

INTERACTIVE

108.9 102.7

63.1 54.5

RIGHT

114.5 108.3

74.1 172

68.0 75.9 65.9 160

(McGHP)

75.2 120.8 117.1

DEAN #37261

NaIO3 1⁄2 Na MoO 2 4 NaN3 (25⬚) NaNO2 (25⬚) NaNO3 NaOH Na picrate (25⬚) 1⁄3 Na PO 3 4 Na propionate (25⬚) 1⁄2 Na S 2 NaSCN 1⁄2 Na SiO 2 3 1⁄2 Na SO 2 4 (mono) Na tartrate 1⁄2 Na WO (25⬚) 2 4 1⁄2 NiSO 4 1⁄2 Oxalic acid 1⁄2 Pb(NO ) 3 2 Propionic acid RbCl RbOH 1⁄4 SnCl 4 1⁄2 SrCl 2 1⁄2 Sr(NO ) 3 2 Tartaric acid (15⬚) 1⁄4 ThCl 4 TlCl TlF TlNO3 1⁄2 Tl SO 2 4 Trichloroacetic acid (25⬚) 1⁄2 UO F (25⬚) 2 2 1⁄2 UO SO (25⬚) 2 4 1⁄3YCl (25⬚) 3 1⁄2 Zn(OAc) (25⬚) 2 1⁄2 ZnCl 2 1⁄2 Zn(NO ) 3 2 1⁄2 ZnSO 4

2.7

49 82

65

55

39.6

29.6

23.2

18.5

45.6

32.3

26.6

20.0

15.9

12.0

9.0

8.167

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8.168

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SECTION 8

TABLE 8.36 Conductivity of Very Pure Water at Various Temperatures and the Equivalent Conductances of Hydrogen and Hydroxyl Ions

cap height base of text

Equivalent conductance, cm2 · ohm⫺1 · equivalent⫺1 Temp., ⬚C

Conductivity, ␮S · cm⫺1

Resistivity, M⍀ · cm

␭0, H⫹

␭0, OH⫺

0 5 10 15 18 20 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100 150 200 250 300

0.011 61 0.016 61 0.023 15 0.031 53 0.037 54 0.042 05 0.055 08 0.070 96 0.090 05 0.112 7 0.139 3 0.170 2 0.205 5 0.245 7 0.291 2 0.341 6 0.397 8 0.459 3 0.525 8 0.597 7 0.675 3 0.756 9 1.84 2.99 3.31 2.42

86.14 60.21 43.21 31.71 26.64 23.78 18.15 14.09 11.10 8.88 7.18 5.88 4.86 4.06 3.43 2.93 2.51 2.18 1.90 1.67 1.48 1.32 0.543 0.334 0.302 0.413

224.1 250.0 275.6 300.9 315.8 325.7 350.1 374.0 397.4 420.0 442.0 463.3 483.8 503.4 522.0 539.7 556.4 572.0 586.4 599.6 611.6 622.2

117.8 133.6 149.6 165.9 491.6 182.5 199.2 216.1 233.0 267.2 267.2 284.3 301.4 318.5 335.4 352.2 368.8 385.2 401.4 417.3 432.8 448.1

824

701

894

821

Source: Data from T. S. Light and S. L. Licht, Anal. Chem., 59:2327–2330 (1987).

8.7.1

Common Conductance Relations*

Conductivity. The standard unit of conductance is electrolytic conductivity (formerly called specific conductance) ␬ , which is defined as the reciprocal of the resistance [⍀⫺1 ] of a 1-m cube of liquid at a specified temperature [⍀⫺1 · m⫺1 ]. See Table 8.33 and the definition of the cell constant. In accurate work at low concentrations it is necessary to subtract the conductivity of the pure solvent (Table 8.34) from that of the solution to obtain the conductivity due to the electrolyte. Resistivity (Specific Resistance)

␳⫽

* SI units are in brackets.

1 ␬

[⍀ · m]

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ELECTROLYTES, EMF, AND CHEMICAL EQUILIBRIUM

8.169

top of rh base of rh cap height base of text

Conductance of an Electrolyte Solution 1 S ⫽␬ R d

[⍀⫺1 ]

where S is the surface area of the electrode, or the mean cross-sectional area of the solution [m2 ], and d is the mean distance between the electrodes [m]. Equivalent Conductivity ⌳⫽

␬ C

[⍀⫺1 · m2 · equiv⫺1 ]

In the older literature, C is the concentration in equivalents per liter. The volume of the solution in cubic centimeters per equivalent is equal to 1000/C, and ⌳ ⫽ 1000 ␬/C, the units employed in Table 8.32 [⍀⫺1 · cm2 · equiv⫺1 ]. The formula unit used in expressing the concentration must be specified; for example, NaCl, 1⁄2 K2SO4 , 1⁄3 LaCl3 . The equivalent conductivity of an electrolyte is the sum of contributions of the individual ions. At infinite dilution: ⌳⬚ ⫽ ␭⬚c ⫹ ␭⬚a , where ␭⬚c and ␭⬚a are the ionic conductances of cations and anions, respectively, at infinite dilution (Table 8.35). Ionic Mobility and Ionic Equivalent Conductivity

␭ c ⫽ Fuc

␭ a ⫽ Fua

and

[⍀⫺1 · m2 · equiv⫺1 ]

where F is the Faraday constant, and uc , ua are the ionic mobilities [m2 · s⫺1 · V⫺1 ]. ⌳ ⫽ ␣ F(uc ⫹ ua ) ⫽ ␣(␭ c ⫹ ␭ a ) where ␣ is the degree of electrolytic dissociation, ⌳/⌳⬚. The electric mobility u of a species is the magnitude of the velocity in an electric field [m · s⫺1 ] divided by the magnitude of the strength of the electric field E[V · m⫺1 ]. Ostwald Dilution Law

␣ 2C 1⫺␣

Kd ⫽

where Kd is the dissociation constant of the weak electrolyte. In general for an electrolyte which yields n ions: Kd ⫽

C (n ⫺ 1)⌳n ⌳⬚ (⌳⬚ ⫺ ⌳) (n ⫺ 1)

Transference Numbers or Hittorf Transport Numbers Tc ⫽

␭c ␭c ⫹ ␭a

Ta ⫽

␭a ␭c ⫹ ␭a

Tc ⫹ Ta ⫽ 1

Tc uc ␭ c ⫽ ⫽ Ta ua ␭ a

␭ c ⫽ Tc ⌳

␭ a ⫽ Ta ⌳ short standard long

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SECTION 9

PHYSICOCHEMICAL RELATIONSHIPS 9.1

LINEAR FREE ENERGY RELATIONSHIPS Table 9.1 Hammett and Taft Substituent Constants Table 9.2 pKⴗa and Rho Values for Hammett Equation Table 9.3 pKⴗa and Rho Values for Taft Equation Table 9.4 Special Hammett Sigma Constants

9.2 9.2 9.6 9.7 9.8

short standard 9.1

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9.2

9.1

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(McGHP)

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SECTION 9

cap height base of text

LINEAR FREE ENERGY RELATIONSHIPS

Many equilibrium and rate processes can be systematized when the influence of each substituent on the reactivity of substrates is assigned a characteristic constant ␴ and the reaction parameter ␳ is known or can be calculated. The Hammett equation log

K ⫽ ␴␳ K⬚

describes the behavior of many meta- and para-substituted aromatic species. In this equation K⬚ is the acid dissociation constant of the reference in aqueous solution at 25⬚C and K is the corresponding constant for the substituted acid. Separate sigma values are defined by this reaction for meta and para substituents and provide a measure of the total electronic influence (polar, inductive, and resonance effects) in the absence of conjugation effects. Sigma constants are not valid of substituents ortho to the reaction center because of anomalous (mainly steric) effects. The inductive effect is transmitted about equally to the meta and para positions. Consequently, ␴m is an approximate measure of the size of the inductive effect of a given substituent and ␴p ⫺ ␴m is an approximate measure of a substituent’s resonance effect. Values of Hammett sigma constants are listed in Table 9.1. Taft sigma values ␴ * perform a similar function with respect to aliphatic and alicyclic systems. Values of ␴ * are listed in Table 9.1. The reaction parameter ␳ depends upon the reaction series but not upon the substituents employed. Values of the reaction parameter for some aromatic and aliphatic systems are given in Tables 9.2 and 9.3. Since substituent effects in aliphatic systems and in meta positions in aromatic systems are essentially inductive in character, ␴ * and ␴m values are often related by the expression ␴m ⫽ 0.217␴ * ⫺ 0.106. Substituent effects fall off with increasing distance from the reaction center; generally a factor of 0.36 corresponds to the interposition of a 9CH2 9 group, which enables ␴ * values to be estimated for R9CH2 9 groups not otherwise available.

TABLE 9.1 Hammett and Taft Substituent Constants Hammett constants Substituent 9 AsO3H⫺ 9 B(OH)2 9 Br 9 CH2Br m-BrC6H4 9 p-BrC6H4 9 9 CH3 9 CH2CH3 9 CH2CH2CH3 9 CH(CH3 )2 9 CH2CH2CH2CH3 9 CH2CH(CH3 )2 9 CH(CH3 )CH2CH3 9 C(CH3 )3 9 CH2CH2CH2CH2CH3 9 CH2CH2CH(CH3 )2

␴m

␴p

⫺0.09 0.01 0.39

⫺0.02 0.45 0.23

⫺0.07 ⫺0.07 ⫺0.05 ⫺0.07 ⫺0.07 ⫺0.07

0.09 0.08 ⫺0.17 ⫺0.15 ⫺0.15 ⫺0.15 ⫺0.16 ⫺0.12 ⫺0.12 ⫺0.20

⫺0.10

Taft constant ␴* 0.06 2.84 1.00

0.0 ⫺0.10 ⫺0.12 ⫺0.19 ⫺0.13 ⫺0.13 ⫺0.19 ⫺0.30 ⫺0.25 ⫺0.17

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9.3

PHYSICOCHEMICAL RELATIONSHIPS

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TABLE 9.1 Hammett and Taft Substituent Constants (Continued) Hammett constants Substituent 9 CH2C(CH3 )3 9 CH2CH2CH2CH2CH2CH2CH3 Cyclopropyl 9 Cyclohexyl 9 9 3,4-(CH2 )2 (fused) 9 3,4-(CH2 )3 9 (fused ring) 9 3,4-(CH)4 9 (fused ring) 9 CH " CH2 9 CH " C(CH3 )2 9 CH " CHCH3 , trans 9 CH2 9 CH " CH2 9 CH " CHC6H5 9 C # CH 9 C # CC6H5 9 CH2 9 C # CH 9 C6H5 p-CH3C6H4 9 Naphthyl 9 (both 1- and 2-) 9 CH2C6H5 9 CH2CH2 9 C6H5 9 CH(CH3 )C6H5 9 CH(C6H5 )2 9 CH2 9 C10H7 2-Furoyl 9 3-Indolyl 9 2-Thienyl 9 2-Thienylmethylene 9 9 CHO 9 COCH3 9 COCH2CH2 9 COCH(CH3 )2 9 COC(CH3 )3 9 COCF3 9 COC6H5 9 CONH2 9 CONHC6H5 9 CH2COCH3 9 CH2CONH2 9 CH2CH2CONH2 9 CH2CH2CH2CONH2 9 CH2CONHC6H5 9 COO⫺ 9 COOH 9 CO 9 OCH3 9 CO 9 OCH2CH3 9 CH2CO 9 OCH3 9 CH2CO 9 OCH2CH3 9 CH2COO 9 CH2CH2COOH 9 Cl 9 CCl3 9 CHCl2

␴m

␴p ⫺0.23

⫺0.07

0.06 0.02

⫺0.21 ⫺0.26 ⫺0.48 0.04

0.14 0.21 0.14

⫺0.05 0.23 0.16

0.06

⫺0.01 ⫺0.5 0.46

0.36 0.38

0.22 0.50 0.48 0.47 0.32

0.65 0.34 0.28

0.46 0.36

⫺0.1 0.36 0.32 0.37

0.0 0.43 0.39 0.45

⫺0.03 0.37 0.47

⫺0.07 0.23

top of rh base of rh

Taft constant ␴* ⫺0.12 ⫺0.37 ⫺0.15

0.56 0.19 0.36 0.0 0.41 2.18 1.35 0.81 0.60 0.75 0.22 ⫺0.06 0.37 0.41 0.44 0.25 ⫺0.06 1.31 0.31 1.65

3.7 2.2 1.68 1.56 0.60 0.31 0.19 0.12 0.0 ⫺1.06 2.08 2.00 2.12 1.06 0.82 ⫺0.06 2.96 2.65 1.94

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9.4

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SECTION 9

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TABLE 9.1 Hammett and Taft Substituent Constants (Continued) Hammett constants Substituent 9 CH2Cl 9 CH2CH2Cl 9 CH2CCl3 9 CH2CH2CCl3 9 CH " CCl2 9 CH2CH " CCl2 p-ClC6H4 9 9F 9 CF3 9 CHF2 9 CH2F 9 CH2CF3 9 CH2CF2CF2CF3 9 C6F5 9 Ge(CH3 )3 9 Ge(CH2CH3 )3 9H 9I 9 CH2I 9 IO2 9 N⫹2 9 N3 (azide) 9 NH2 9 NH⫹3 9 CH2 9 NH2 9 CH2 9 NH⫹3 9 NH 9 CH3 9 NH 9 C2H5 9 NH 9 C4H9 9 NH(CH3 )⫹2 9 NH2 9 CH3⫹ 9 NH2 9 C2H⫹5 9 N(CH3 )⫹3 9 N(CH3 )2 9 CH2 9 N(CH3 )3⫹ 9 N(CF3 )2 p-H2N 9 C6H5 9 9 NH 9 CO 9 CH3 9 NH 9 CO 9 C2H5 9 NH 9 CO 9 C6H5 9 NH 9 CHO 9 NH 9 CO 9 NH2 9 NH 9 OH 9 NH 9 CO 9 OC2H5 9 CH2 9 NH 9 CO 9 CH3 9 NH 9 SO2 9 C6H5 9 NH 9 NH2 9 CN 9 CH2 9 CN 9 NO 9 NO2 9 CH2 9 NO2

␴m

␴p

0.12

0.18

0.34 0.43

0.08 0.06 0.54

⫺0.12

0.00 0.35

⫺0.03 0.0 0.0 0.00 0.28

0.70 1.76 0.33 ⫺0.16 1.13

0.76 1.91 0.08 ⫺0.66 1.70

⫺0.30 ⫺0.24 ⫺0.34

⫺0.84 ⫺0.61 ⫺0.51

0.96 0.96 0.88 ⫺0.2 0.45 0.21 0.22 0.25 0.18 ⫺0.04 0.33 ⫺0.02 0.56 0.17 0.71

0.82 ⫺0.83 0.53 ⫺0.30 0.00 0.08

Taft constant ␴* 1.05 0.38 0.75 0.25 1.00 0.19 3.21 2.61 2.05 1.10 0.90 0.87

0.49 2.46 0.85

2.62 0.62 3.76 0.50 2.24

4.36 3.74 3.74 4.55 0.32 1.90

1.40 1.56 1.68 1.62 1.31

⫺0.34 1.99 0.43 1.99 ⫺0.55 0.66 0.01 0.12 0.78

3.30 1.30 4.0 1.40

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PHYSICOCHEMICAL RELATIONSHIPS

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TABLE 9.1 Hammett and Taft Substituent Constants (Continued) Hammett constants Substituent 9 CH2 9 CH2 9 NO2 9 CH " CHNO2 m-O2N 9 C6H4 p-O2N 9 C6H4 (NO2 )3C6H2 9 (picryl) 9 N(CO 9 CH3 )(CO 9 C6H5 ) 9 N(CO 9 CH3 )(naphthyl) 9 O⫺ 9 OH 9 O 9 CH3 9 O 9 C2H5 9 O 9 C3H7 9 O 9 CH(CH3 )2 9 O 9 C4H9 9 O 9 cyclopentyl 9 O 9 cyclohexyl 9 O 9 CH2 9 cyclohexyl 9 O 9 C6H5 9 O 9 CH2 9 C6H5 9 OCF3 3,4-O 9 CH2 9 O 9 3,4-O 9 (CH2 9 )2O 9 9 O 9 CO 9 CH3 9 ONO2 9 O 9 N " C(CH3 )2 9 ONH⫹3 9 CH2 9 O⫺ 9 CH2 9 OH 9 CH2 9 O 9 CH3 9 CH(OH) 9 CH3 9 CH(OH) 9 C6H5 p-HO 9 C6H4 9 p-CH3O 9 C6H4 9 9 CH2 9 CH(OH) 9 CH3 9 CH2 9 C(OH)(CH3 )2 9 P(CH3 )2 9 P(CH3)3⫹ 9 P(CF3 )2 9 PO3H⫺ 9 PO(OC2H5)2 9 SH 9 SCH3 9 S(CH3 )⫹2 9 SCH2CH3 9 SCH2CH2CH3 9 SCH2CH2CH2CH3 9 S 9 cyclohexyl 9 SC6H5 9 SC(C6H5)3 9 SCH2C6H5 9 SCH2CH2C6H5 9 CH2SH

␴m

␴p

0.33

0.26 0.18 0.24 0.41

top of rh base of rh

Taft constant ␴* 0.50

0.43

1.37 1.65 ⫺0.71 0.12 0.12 0.10 0.00 0.05 ⫺0.05 0.29 0.18 0.25 0.40

0.39

0.08

⫺0.52 ⫺0.37 ⫺0.27 ⫺0.24 ⫺0.25 ⫺0.45 ⫺0.32

⫺0.32 ⫺0.42 0.35 ⫺0.27 ⫺0.12 0.31

0.08

⫺0.24 ⫺0.10

0.1 0.8 0.6 0.2 0.55 0.25 0.15 1.0 0.23

0.30

0.03

0.05 0.9 0.7 0.26 0.60 0.15 0.00 0.9 0.03

1.34 1.81 1.68 1.68 1.62 1.68 1.62 1.81 1.31 2.43

3.86 1.81 2.92 0.27 0.31 0.52 0.12 0.50 ⫺0.06 ⫺0.25

1.68 1.56 1.56 1.49 1.44 1.93 1.87 0.69 1.56 1.44 0.62

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SECTION 9

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TABLE 9.1 Hammett and Taft Substituent Constants (Continued) Taft constant ␴*

Hammett constants Substituent 9 CH2SCH2C6H5 9 SCF3 9 SCN 9 S 9 CO 9 CH3 9 S 9 CONH2 9 SO 9 CH3 9 SO 9 C6H5 9 CH2 9 SO 9 CH3 9 SO2 9 CH3 9 SO2 9 CH2CH3 9 SO2 9 CH2CH2CH3 9 SO2 9 C6H5 9 SO2 9 CF3 9 SO2 9 NH2 9 CH2 9 SO2 9 CH3 9 SO⫺3 9 SO3H 9 SeCH3 9 Se 9 cyclohexyl 9 SeCN 9 Si(CH3 )3 9 Si(CH2CH3 )3 9 Si(CH3 )2C6H5 9 Si(CH3)2 9 O 9 Si(CH3 )3 9 CH2Si(CH3 )3 9 CH2CH2Si(CH3 )3 9 Sn(CH3 )3 9 Sn(CH2CH3)3

␴m

␴p

0.40 0.63 0.39 0.34 0.52

0.50 0.52 0.44

0.37

2.07 0.49

0.60

0.68

0.67 0.79 0.46

0.93 0.57

0.05 0.1 0.67 ⫺0.04

⫺0.16

3.43

3.24 1.33 3.68 3.74 3.68 3.55

1.38 0.81

0.09 0.50 0.0

2.37 3.61 ⫺0.81

0.66 ⫺0.07 0.0

⫺0.87 ⫺0.81 ⫺0.25 ⫺0.25

⫺0.22 0.0 0.0

TABLE 9.2 pK⬚a and Rho Values for Hammett Equation Acid Arenearsonic acids pK1 pK2 Areneboronic acids (in aqueous 25% ethanol) Arenephosphonic acids pK1 pK2 ␣-Aryladoximes Benzeneseleninic acids Benzenesulfonamides (20⬚C) Benzenesulfonanilides (20⬚C) X 9 C6H4 9 SO2 9 NH 9 C6H5 C6H5 9 SO2 9 NH 9 C6H4 9 X Benzoic acids Cinnamic acids Phenols

pK⬚a

␳

3.54 8.49 9.70

1.05 0.87 2.15

1.84 6.97 10.70 4.78 10.00

0.76 0.95 0.86 1.03 1.06

8.31 8.31 4.21 4.45 9.92

1.16 1.74 1.00 0.47 2.23

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9.7

PHYSICOCHEMICAL RELATIONSHIPS

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TABLE 9.2 pK⬚a and Rho Values for Hammett Equation (Continued) Acid

␳

pK⬚a

Phenylacetic acids Phenylpropiolic acids (in aqueous 35% dioxane) Phenylpropionic acids Phenyltrifluoromethylcarbinols Pyridine-1-oxides 2-Pyridones 4-Pyridones Pyrroles 5-Substituted pyrrole-2-carboxylic acids Thiobenzoic acids Thiophenols Trifluoroacetophenone hydrates 5-Substituted topolones Protonated cations of Acetophenones Anilines C-Aryl-N-dibutylamidines (in aqueous 50% ethanol) N,N-Dimethylanilines Isoquinolines 1-Naphthylamines 2-Naphthylamines Pyridines Quinolines

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4.30 3.24 4.45 11.90 0.94 11.65 11.12 17.00 2.82 2.61 6.50 10.00 6.42

0.49 0.81 0.21 1.01 2.09 4.28 4.28 4.28 1.40 1.0 2.2 1.11 3.10

⫺6.0 4.60 11.14 5.07 5.32 3.85 4.29 5.18 4.88

2.6 2.90 1.41 3.46 5.90 2.81 2.81 5.90 5.90

TABLE 9.3 pK⬚a and Rho Values for Taft Equation Acid RCOOH RCH2COOH RC # C 9 COOH H2C " C(R) 9 COOH (CH3 )2C " C(R) 9 COOH cis-C6H5 9 CH " C(R) 9 COOH trans-C6H5 9 CH " C(R) 9 COOH R 9 CO 9 CH2 9 COOH HON " C(R) 9 COOH RCH2OH RCH(OH)2 R1CO 9 NHR2 CH3CO 9 C(R) " C(OH)CH3 CH3CO 9 CH(R) 9 CO 9 OC2H5 R 9 CO 9 NHOH R1R2C " NOH (R1 , R2 not acyl groups) (R)(CH3CO)C " NOH RC(NO2)2H RSH RCH2SH R 9 CO 9 SH

pK⬚a 4.66 4.76 2.39 4.39 4.65 3.77 4.61 4.12 4.84 15.9 14.4 22.0 9.25 12.59 9.48 12.35 9.00 5.24 10.22 10.54 3.52

␳ 1.62 0.67 1.89 0.64 0.47 0.63 0.47 0.43 0.34 1.42 1.42 3.1* 1.78 3.44 0.98 1.18 0.94 3.60 3.50 1.47 1.62

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TABLE 9.3 pK⬚a and Rho Values for Taft Equation (Continued) Acid

␳

pK⬚a

Protonated cations of RNH2 R1R2NH R1R2R3N R1R2PH R1R2R3P

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10.15 10.59 9.61 3.59 7.85

3.14 3.23 3.30 2.61 2.67

* ␴ * for R 1CO and R 2 .

Two modified sigma constants have been formulated for situations in which the substituent enters into resonance with the reaction center in an electron-demanding transition state (␴ ⫹ ) or for an electron-rich transition state (␴ ⫺ ). ␴ ⫺ constants give better correlations in reactions involving phenols, anilines, and pyridines and in nucleophilic substitutions. Values of some modified sigma constants are given in Table 9.4.

TABLE 9.4 Special Hammett Sigma Constants Substituent

␴ ⫹m

␴ ⫹p

␴ ⫺p

9 CH3 9 C(CH3 )3 9 C6H5 9 CF3 9F 9 Cl 9 Br 9I 9 CN 9 CHO 9 CONH2 9 COCH3 9 COOH 9 CO 9 OCH3 9 CO 9 OCH2CH3 9 N2⫹ 9 NH2 9 N(CH3 )2 9 N(CH3 )3⫹ 9 NH 9 CO 9 CH3 9 NO2 9 OH 9 O⫺ 9 OCH3 9 SF5 9 SCF3 9 SO2CH3 9 SO2CF3

⫺0.07 ⫺0.06 0.11 0.52 0.35 0.40 0.41 0.36 0.56

⫺0.31 ⫺0.26 ⫺0.18 0.61 ⫺0.07 0.11 0.15 0.14 0.66

⫺0.17

0.32 0.37 0.37

0.42 0.49 0.48

0.16

⫺1.3 ⫺1.7 0.41 ⫺0.60 0.79 ⫺0.92

0.36 0.67

0.05

⫺0.78

0.74 0.02 0.23 0.26 0.88 1.13 0.63 0.85 0.73 0.66 0.68 3.2 ⫺0.66

1.25 ⫺0.81 ⫺0.27 0.70 0.57 1.05 1.36

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POLYMERS, RUBBERS, FATS, OILS, AND WAXES 10.1 POLYMERS 10.2 ADDITIVES TO POLYMERS 10.2.1 Antioxidants 10.2.2 Antistatic Agents 10.2.3 Chain-Transfer Agents 10.2.4 Coupling Agents 10.2.5 Flame Retardants 10.2.6 Foaming Agents (Chemical Blowing Agents) 10.2.7 Inhibitors 10.2.8 Lubricants Table 10.1 Plastic Families 10.2.9 Plasticizers 10.2.10 Ultraviolet Stabilizers 10.2.11 Vulcanization and Curing 10.3 FORMULAS AND KEY PROPERTIES OF PLASTIC MATERIALS 10.3.1 Acetals 10.3.2 Acrylics 10.3.3 Alkyds 10.3.4 Alloys 10.3.5 Allyls 10.3.6 Cellulosics 10.3.7 Epoxy 10.3.8 Fluorocarbon 10.3.9 Nitrile Resins 10.3.10 Melamine Formaldehyde 10.3.11 Phenolics 10.3.12 Polyamides 10.3.13 Poly(amide-imide) 10.3.14 Polycarbonate 10.3.15 Polyester 10.3.16 Poly(methylpentene) 10.3.17 Polyolefins 10.3.18 Poly(phenylene Sulfide) 10.3.19 Polyurethane 10.3.20 Silicones 10.3.21 Styrenics 10.3.22 Sulfones 10.3.23 Thermoplastic Elastomers 10.3.24 Vinyl 10.3.25 Urea Formaldehyde Table 10.2 Properties of Commercial Plastics 10.4 FORMULAS AND ADVANTAGES OF RUBBERS 10.4.1 Gutta Percha 10.4.2 Natural Rubber 10.4.3 Chlorosulfonated Polyethylene 10.4.4 Epichlorohydrin 10.4.5 Nitrile Rubber (NBR, GRN, Buna N) 10.1

10.2 10.4 10.4 10.4 10.4 10.4 10.5 10.5 10.6 10.6 10.6 10.7 10.7 10.7 10.8 10.8 10.8 10.9 10.10 10.10 10.10 10.11 10.12 10.13 10.13 10.14 10.14 10.15 10.15 10.15 10.16 10.16 10.17 10.18 10.18 10.19 10.20 10.20 10.20 10.21 10.22 10.58 10.58 10.58 10.58 10.59 10.59

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10.4.6 Polyacrylate 10.4.7 cis-Polybutadiene Rubber (BR) 10.4.8 Polychloroprene (Neoprene) 10.4.9 Ethylene-Propylene-Diene Rubber (EPDM) 10.4.10 Polyisobutylene (Butyl Rubber) 10.4.11 (Z)-Polyisoprene (Synthetic Natural Rubber) 10.4.12 Polysulfide Rubbers 10.4.13 Poly(vinyl Chloride) (PVC) 10.4.14 Silicone Rubbers 10.4.15 Styrene-Butadiene Rubber (GRS, SBR, Buna S) 10.4.16 Urethane Table 10.3 Properties of Natural and Synthetic Rubbers 10.5 CHEMICAL RESISTANCE Table 10.4 Resistance of Selected Polymers and Rubbers to Various Chemicals at 20ⴗC 10.6 GAS PERMEABILITY Table 10.5 Gas Permeability Constants (1010 P ) at 25ⴗC for Polymers and Rubbers Table 10.6 Vapor Permeability Constants (1010 P) at 35ⴗC for Polymers 10.7 FATS, OILS, AND WAXES Table 10.7 Constants of Fats and Oils Table 10.8 Constants of Waxes

10.1

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10.59 10.59 10.60 10.60 10.60 10.60 10.61 10.61 10.61 10.61 10.62 10.63 10.64

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10.64 10.66 10.66 10.69 10.69 10.69 10.72

POLYMERS

Polymers are mixtures of macromolecules with similar structures and molecular weights that exhibit some average characteristic properties. In some polymers long segments of linear polymer chains are oriented in a regular manner with respect to one another. Such polymers have many of the physical characteristics of crystals and are said to be crystalline. Polymers that have polar functional groups show a considerable tendency to be crystalline. Orientation is aided by alignment of dipoles on different chains. Van der Waals’ interactions between long hydrocarbon chains may provide sufficient total attractive energy to account for a high degree of regularity within the polymers. Irregularities such as branch points, comonomer units, and cross-links lead to amorphous polymers. They do not have true melting points but instead have glass transition temperatures at which the rigid and glasslike material becomes a viscous liquid as the temperature is raised. Elastomers. Elastomers is a generic name for polymers that exhibit rubberlike elasticity. Elastomers are soft yet sufficiently elastic that they can be stretched several hundred percent under tension. When the stretching force is removed, they retract rapidly and recover their original dimensions. Polymers that soften or melt and then solidify and regain their original properties on cooling are called thermoplastic. A thermoplastic polymer is usually a single strand of linear polymer with few if any cross-links. Thermosetting Polymers. Polymers that soften or melt on warming and then become infusible solids are called thermosetting. The term implies that thermal decomposition has not taken place. Thermosetting plastics contain a cross-linked polymer network that extends through the finished article, making it stable to heat and insoluble in organic solvents. Many molded plastics are shaped while molten and are then heated further to become rigid solids of desired shapes.

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Synthetic Rubbers. Synthetic rubbers are polymers with rubberlike characteristics that are prepared from dienes or olefins. Rubbers with special properties can also be prepared from other polymers, such as polyacrylates, fluorinated hydrocarbons, and polyurethanes. Structural Differences. Polymers exhibit structural differences. A linear polymer consists of long segments of single strands that are oriented in a regular manner with respect to one another. Branched polymers have substituents attached to the repeating units that extend the polymer laterally. When these units participate in chain propagation and link together chains, a cross-linked polymer is formed. A ladder polymer results when repeating units have a tetravalent structure such that a polymer consists of two backbone chains regularly cross-linked at short intervals. Generally polymers involve bonding of the most substituted carbon of one monomeric unit to the least substituted carbon atom of the adjacent unit in a head-to-tail arrangement. Substituents appear on alternate carbon atoms. Tacticity refers to the configuration of substituents relative to the backbone axis. In an isotactic arrangement, substituents are on the same plane of the backbone axis; that is, the configuration at each chiral center is identical.

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In a syndiotactic arrangement, the substituents are in an ordered alternating sequence, appearing alternately on one side and then on the other side of the chain, thus

In an atactic arrangement, substituents are in an unordered sequence along the polymer chains. Copolymerization. Copolymerization occurs when a mixture of two or more monomer types polymerizes so that each kind of monomer enters the polymer chain. The fundamental structure resulting from copolymerization depends on the nature of the monomers and the relative rates of monomer reactions with the growing polymer chain. A tendency toward alternation of monomer units is common. 9X9Y 9 X 9 Y 9X 9Y 9 Random copolymerization is rather unusual. Sometimes a monomer which does not easily form a homopolymer will readily add to a reactive group at the end of a growing polymer chain. In turn, that monomer tends to make the other monomer much more reactive. In graft copolymers the chain backbone is composed of one kind of monomer and the branches are made up of another kind of monomer.

The structure of a block copolymer consists of a homopolymer attached to chains of another homopolymer. 9XXXX9YYY 9 XXXX 9YYY 9 Configurations around any double bond give rise to cis and trans stereoisomerism.

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ADDITIVES TO POLYMERS

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Antioxidants

Antioxidants markedly retard the rate of autoxidation throughout the useful life of the polymer. Chain-terminating antioxidants have a reactive 9NH or 9 OH functional group and include compounds such as secondary aryl amines or hindered phenols. They function by transfer of hydrogen to free radicals, principally to peroxy radicals. Butylated hydroxytoluene is a widely used example. Peroxide-decomposing antioxidants destroy hydroperoxides, the sources of free radicals in polymers. Phosphites and thioesters such as tris(nonylphenyl) phosphite, distearyl pentaerythritol diphosphite, and dialkyl thiodipropionates are examples of peroxide-decomposing antioxidants.

10.2.2

Antistatic Agents

External antistatic agents are usually quaternary ammonium salts of fatty acids and ethoxylated glycerol esters of fatty acids that are applied to the plastic surface. Internal antistatic agents are compounded into plastics during processing. Carbon blacks provide a conductive path through the bulk of the plastic. Other types of internal agents must bloom to the surface after compounding in order to be active. These latter materials are ethoxylated fatty amines and ethoxylated glycerol esters of fatty acids, which often must be individually selected to match chemically each plastic type. Antistatic agents require ambient moisture to function. Consequently their effectiveness is dependent on the relative humidity. They provide a broad range of protection at 50% relative humidity. Much below 20% relative humidity, only materials which provide a conductive path through the bulk of the plastic to ground (such as carbon black) will reduce electrostatic charging.

10.2.3

Chain-Transfer Agents

Chain-transfer agents are used to regulate the molecular weight of polymers. These agents react with the developing polymer and interrupt the growth of a particular chain. The products, however, are free radicals that are capable of adding to monomers and initiating the formation of new chains. The overall effect is to reduce the average molecular weight of the polymer without reducing the rate of polymerization. Branching may occur as a result of chain transfer between a growing but rather short chain with another and longer polymer chain. Branching may also occur if the radical end of a growing chain abstracts a hydrogen from a carbon atom four or five carbons removed from the end. Thiols are commonly used as chain-transfer agents.

10.2.4

Coupling Agents

Coupling agents are molecular bridges between the interface of an inorganic surface (or filler) and an organic polymer matrix. Titanium-derived coupling agents interact with the free protons at the inorganic interface to form organic monomolecular layers on the inorganic surface. The titanatecoupling-agent molecule has six functions:

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where

Type

m

n

Monoalkoxy Coordinate Chelate

1 4 1

3 2 2

Function 1 is the attachment of the hydrolyzable portion of the molecule to the surface of the inorganic (or proton-bearing) species. Function 2 is the ability of the titanate molecule to transesterify. Function 3 affects performance as determined by the chemistry of alkylate, carboxyl, sulfonyl, phenolic, phosphate, pyrophosphate, and phosphite groups. Function 4 provides van der Waals’ entanglement via long carbon chains. Function 5 provides thermoset reactivity via functional groups such as methacrylates and amines. Function 6 permits the presence of two or three pendent organic groups. This allows all functionality to be controlled to the first-, second-, or third-degree levels. Silane coupling agents are represented by the formula Z9R 9SiY3 where Y represents a hydrolyzable group (typically alkoxy); Z is a functional organic group, such as amino, methacryloxy, epoxy; and R typically is a small aliphatic linkage that serves to attach the functional organic group to silicon in a stable fashion. Bonding to surface hydroxy groups of inorganic compounds is accomplished by the 9 SiY3 portion, either by direct bonding of this group or more commonly via its hydrolysis product 9Si(OH)3 . Subsequent reaction of the functional organic group with the organic matrix completes the coupling reaction and establishes a covalent chemical bond from the organic phase through the silane coupling agent to the inorganic phase. 10.2.5

Flame Retardants

Flame retardants are thought to function via several mechanisms, dependent upon the class of flame retardant used. Halogenated flame retardants are thought to function principally in the vapor phase either as a diluent and heat sink or as a free-radical trap that stops or slows flame propagation. Phosphorus compounds are thought to function in the solid phase by forming a glaze or coating over the substrate that prevents the heat and mass transfer necessary for sustained combustion. With some additives, as the temperature is increased, the flame retardant acts as a solvent for the polymer, causing it to melt at lower temperatures and flow away from the ignition source. Mineral hydrates, such as alumina trihydrate and magnesium sulfate heptahydrate, are used in highly filled thermoset resins. 10.2.6

Foaming Agents (Chemical Blowing Agents)

Foaming agents are added to polymers during processing to form minute gas cells throughout the product. Physical foaming agents include liquids and gases. Compressed nitrogen is often used in

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injection molding. Common liquid foaming agents are short-chain aliphatic hydrocarbons in the C5 to C7 range and their chlorinated or fluorinated analogs. The chemical foaming agent used varies with the temperature employed during processing. At relatively low temperatures (15 to 200⬚C), the foaming agent is often 4,4⬘-oxybis(benzenesulfonylhydrazide) or p-toluenesulfonylhydrazide. In the midrange (160 to 232⬚C), either sodium hydrogen carbonate or 1,1⬘azobisformamide is used. For the high range (200 to 285⬚C), there are p-toluenesulfonyl semicarbazide, 5-phenyltetrazole and analogs, and trihydrazinotriazine.

10.2.7

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Inhibitors

Inhibitors slow or stop polymerization by reacting with the initiator or the growing polymer chain. The free radical formed from an inhibitor must be sufficiently unreactive that it does not function as a chain-transfer agent and begin another growing chain. Benzoquinone is a typical free-radical chain inhibitor. The resonance-stabilized free radical usually dimerizes or disproportionates to produce inert products and end the chain process.

10.2.8

Lubricants

Materials such as fatty acids are added to reduce the surface tension and improve the handling qualities of plastic films.

TABLE 10.1 Plastic Families Acetals Acrylics Poly(methyl methacrylate) (PMMA) Poly(acrylonitrile) Alkyds Alloys Acrylic-poly(vinyl chloride) alloy Acrylonitrile-butadiene-styrene-poly(vinyl chloride) alloy (ABS-PVC) Acrylonitrile-butadiene-styrene-polycarbonate alloy (ABS-PC) Allyls Allyl-diglycol-carbonate polymer Diallyl phthalate (DAP) polymer Cellulosics Cellulose acetate resin Cellulose-acetate-propionate resin Cellulose-acetate-butyrate resin Cellulose nitrate resin Ethyl cellulose resin Rayon Chlorinated polyether Epoxy Fluorocarbons Poly(tetrafluoroethylene) (PTFE) Poly(chlorotrifluoroethylene) (PCTFE) Perfluoroalkoxy (PFA) resin Fluorinated ethylene-propylene (FEP) resin

Fluorocarbons (continued) Poly(vinylidene fluoride) (PVDF) Ethylene-chlorotrifluoroethylene copolymer Ethylene-tetrafluoroethylene copolymer Poly(vinyl fluoride) (PVF) Melamine formaldehyde Melamine phenolic Nitrile resins Phenolics Polyamides Nylon 6 Nylon 6/6 Nylon 6/9 Nylon 6/12 Nylon 11 Nylon 12 Aromatic nylons Poly(amide-imide) Poly(aryl ether) Polycarbonate (PC) Polyesters Poly(butylene terephthalate) (PBT) [also called polytetramethylene terephthalate (PTMT)] Poly(ethylene terephthalate) (PET) Unsaturated polyesters (SMC, BMC) Butadiene-maleic acid copolymer (BMC) Styrene-maleic acid copolymer (SMC) Polyimide

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TABLE 10.1 Plastic Families (Continued) Poly(methylpentene) Polyolefins (PO) Low-density polyethylene (LDPE) High-density polyethylene (HDPE) Ultrahigh-molecular-weight polyethylene (UHMWPE) Polypropylene (PP) Polybutylene (PB) Polyallomers Poly(phenylene oxide) Poly(phenylene sulfide) (PPS) Polyurethanes Silicones Styrenics Polystyrene (PS) Acrylonitrile-butadiene-styrene (ABS) copolymer Styrene-acrylonitrile (SAN) copolymer Styrene-butadiene copolymer Sulfones Polysulfone (PSF)

10.2.9

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Sulfones (continued) Poly(ether sulfone) Poly(phenyl sulfone) Thermoplastic elastomers Polyolefin Polyester Block copolymers Styrene-butadiene block copolymer Styrene-isoprene block copolymer Styrene-ethylene block copolymer Styrene-butylene block copolymer Urea formaldehyde Vinyls Poly(vinyl chloride) (PVC) Poly(vinyl acetate) (PVAC) Poly(vinylidene chloride) Poly(vinyl butyrate) (PVB) Poly(vinyl formal) Poly(vinyl alcohol) (PVAL)

Plasticizers

Plasticizers are relatively nonvolatile liquids which are blended with polymers to alter their properties by intrusion between polymer chains. Diisooctyl phthalate is a common plasticizer. A plasticizer must be compatible with the polymer to avoid bleeding out over long periods of time. Products containing plasticizers tend to be more flexible and workable.

10.2.10

Ultraviolet Stabilizers

2-Hydroxybenzophenones represent the largest and most versatile class of ultraviolet stabilizers that are used to protect materials from the degradative effects of ultraviolet radiation. They function by absorbing ultraviolet radiation and by quenching electronically excited states. Hindered amines, such as 4-(2,2,6,6-tetramethylpiperidinyl) decanedioate, serve as radical scavengers and will protect thin films under conditions in which ultraviolet absorbers are ineffective. Metal salts of nickel, such as dibutyldithiocarbamate, are used in polyolefins to quench singlet oxygen or electronically excited states of other species in the polymer. Zinc salts function as peroxide decomposers.

10.2.11

Vulcanization and Curing

Originally, vulcanization implied heating natural rubber with sulfur, but the term is now also employed for curing polymers. When sulfur is employed, sulfide and disulfide cross-links form between polymer chains. This provides sufficient rigidity to prevent plastic flow. Plastic flow is a process in which coiled polymers slip past each other under an external deforming force; when the force is released, the polymer chains do not completely return to their original positions. Organic peroxides are used extensively for the curing of unsaturated polyester resins and the polymerization of monomers having vinyl unsaturation. The 9O 9O 9 bond is split into free radicals which can initiate polymerization or cross-linking of various monomers or polymers.

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FORMULAS AND KEY PROPERTIES OF PLASTIC MATERIALS

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Acetals

10.3.1.1 Homopolymer. Acetal homopolymers are prepared from formaldehyde and consist of high-molecular-weight linear polymers of formaldehyde.

The good mechanical properties of this homopolymer result from the ability of the oxymethylene chains to pack together into a highly ordered crystalline configuration as the polymers change from the molten to the solid state. Key properties include high melt point, strength and rigidity, good frictional properties, and resistance to fatigue. Higher molecular weight increases toughness but reduces melt flow. 10.3.1.2 Copolymer. Acetal copolymers are prepared by copolymerization of 1,3,5-trioxane with small amounts of a comonomer. Carbon-carbon bonds are distributed randomly in the polymer chain. These carbon-carbon bonds help to stabilize the polymer against thermal, oxidative, and acidic attack.

10.3.2

Acrylics

10.3.2.1 Poly(methyl Methacrylate). The monomer used for poly(methyl methacrylate), 2-hydroxy-2-methylpropanenitrile, is prepared by the following reaction:

2-Hydroxy-2-methylpropanenitrile is then reacted with methanol (or other alcohol) to yield methacrylate ester. Free-radical polymerization is initiated by peroxide or azo catalysts and produce poly(methyl methacrylate) resins having the following formula:

Key properties are improved resistance to heat, light, and weathering. This polymer is unaffected by most detergents, cleaning agents, and solutions of inorganic acids, alkalies, and aliphatic hydrocarbons. Poly(methyl methacrylate) has light transmittance of 92% with a haze of 1 to 3% and its clarity is equal to glass.

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10.3.2.2 Poly(methyl Acrylate). The monomer used for preparing poly(methyl acrylate) is produced by the oxidation of propylene. The resin is made by free-radical polymerization initiated by peroxide or azo catalysts and has the following formula:

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Resins vary from soft, elastic, film-forming materials to hard plastics. 10.3.2.3 Poly(acrylic Acid) and Poly(methacrylic Acid). Glacial acrylic acid and glacial methacrylic acid can be polymerized to produce water-soluble polymers having the following structures:

These monomers provide a means for introducing carboxyl groups into copolymers. In copolymers these acids can improve adhesion properties, improve freeze-thaw and mechanical stability of polymer dispersions, provide stability in alkalies (including ammonia), increase resistance to attack by oils, and provide reactive centers for cross-linking by divalent metal ions, diamines, or epoxides. 10.3.2.4 Functional Group Methacrylate Monomers. Hydroxyethyl methacrylate and dimethylaminoethyl methacrylate produce polymers having the following formulas:

The use of hydroxyethyl (also hydroxypropyl) methacrylate as a monomer permits the introduction of reactive hydroxyl groups into the copolymers. This offers the possibility for subsequent crosslinking with an HO-reactive difunctional agent (diisocyanate, diepoxide, or melamine-formaldehyde resin). Hydroxyl groups promote adhesion to polar substrates. Use of dimethylaminoethyl (also tert-butylaminoethyl) methacrylate as a monomer permits the introduction of pendent amino groups which can serve as sites for secondary cross-linking, provide a way to make the copolymer acid-soluble, and provide anchoring sites for dyes and pigments. 10.3.2.5 Poly(acrylonitrile). Poly(acrylonitrile) polymers have the following formula:

10.3.3

Alkyds

Alkyds are formulated from polyester resins, cross-linking monomers, and fillers of mineral or glass. The unsaturated polyester resins used for thermosetting alkyds are the reaction products of polyfunctional organic alcohols (glycols) and dibasic organic acids.

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Key properties of alkyds are dimensional stability, colorability, and arc track resistance. Chemical resistance is generally poor.

10.3.4

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Alloys

Polymer alloys are physical mixtures of structurally different homopolymers or copolymers. The mixture is held together by secondary intermolecular forces such as dipole interaction, hydrogen bonding, or van der Waals’ forces. Homogeneous alloys have a single glass transition temperature which is determined by the ratio of the components. The physical properties of these alloys are averages based on the composition of the alloy. Heterogeneous alloys can be formed when graft or block copolymers are combined with a compatible polymer. Alloys of incompatible polymers can be formed if an interfacial agent can be found.

10.3.5 10.3.5.1

Allyls Diallyl Phthalate (and Diallyl 1,3-Phthalate). These allyl polymers are prepared from

These resulting polymers are solid, linear, internally cyclized, thermoplastic structures containing unreacted allylic groups spaced at regular intervals along the polymer chain. Molding compounds with mineral, glass, or synthetic fiber filling exhibit good electrical properties under high humidity and high temperature conditions, stable low-loss factors, high surface and volume resistivity, and high arc and track resistance.

10.3.6 10.3.6.1 tion:

Cellulosics Cellulose Triacetate.

Cellulose triacetate is prepared according to the following reac-

Because cellulose triacetate has a high softening temperature, it must be processed in solution. A mixture of dichloromethane and methanol is a common solvent. Cellulose triacetate sheeting and film have good gauge uniformity and good optical clarity. Cellulose triacetate products have good dimensional stability and resistance to water and have good folding endurance and burst strength. It is highly resistant to solvents such as acetone. Cellulose triacetate products have good heat resistance and a high dielectric constant. 10.3.6.2 Cellulose Acetate, Propionate, and Butyrate. Cellulose acetate is prepared by hydrolyzing the triester to remove some of the acetyl groups; the plastic-grade resin contains 38 to 40%

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acetyl. The propionate and butyrate esters are made by substituting propionic acid and its anhydride (or butyric acid and its anhydride) for some of the acetic acid and acetic anhydride. Plastic grades of cellulose-acetate-propionate resin contain 39 to 47% propionyl and 2 to 9% acetyl; celluloseacetate-butyrate resins contain 26 to 39% butyryl and 12 to 15% acetyl. These cellulose esters form tough, strong, stiff, hard plastics with almost unlimited color possibilities. Articles made from these plastics have a high gloss and are suitable for use in contact with food. 10.3.6.3

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Cellulose Nitrate. Cellulose nitrate is prepared according to the following reaction: C6H10O5 ⫹ HNO3 : [ 9C6H7O2(OH)(ONO2 )2 9 ]n

The nitrogen content for plastics is usually about 11%, for lacquers and cement base it is 12%, and for explosives it is 13%. The standard plasticizer added is camphor. Key properties of cellulose nitrate are good dimensional stability, low water absorption, and toughness. Its disadvantages are its flammability and lack of stability to heat and sunlight. 10.3.6.4 Ethyl Cellulose. Ethyl cellulose is prepared by reacting cellulose with caustic to form caustic cellulose, which is then reacted with chloroethane to form ethyl cellulose. Plastic-grade material contains 44 to 48% ethoxyl. Although not as resistant as cellulose esters to acids, it is much more resistant to bases. An outstanding feature is its toughness at low temperatures. 10.3.6.5 Rayon. Viscose rayon is obtained by reacting the hydroxy groups of cellulose with carbon disulfide in the presence of alkali to give xanthates. When this solution is poured (spun) into an acid medium, the reaction is reversed and the cellulose is regenerated (coagulated).

10.3.7

Epoxy

Epoxy resin is prepared by the following condensation reaction:

The condensation leaves epoxy end groups that are then reacted in a separate step with nucleophilic compounds (alcohols, acids, or amines). For use as an adhesive, the epoxy resin and the curing resin (usually an aliphatic polyamine) are packaged separately and mixed together immediately before use. Epoxy novolac resins are produced by glycidation of the low-molecular-weight reaction products of phenol (or cresol) with formaldehyde. Highly cross-linked systems are formed that have superior performance at elevated temperatures.

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Fluorocarbon

10.3.8.1 Poly(tetrafluoroethylene). Poly(tetrafluoroethylene) is prepared from tetrafluoroethylene and consists of repeating units in a predominantly linear chain: F2C"CF2 : [ 9CF2 9 CF2 9]n Tetrafluoroethylene polymer has the lowest coefficient of friction of any solid. It has remarkable chemical resistance and a very low brittleness temperature (⫺100⬚C). Its dielectric constant and loss factor are low and stable across a broad temperature and frequency range. Its impact strength is high. 10.3.8.2 Fluorinated Ethylene-Propylene Resin. Polymer molecules of fluorinated ethylenepropylene consist of predominantly linear chains with this structure:

Key properties are its flexibility, translucency, and resistance to all known chemicals except molten alkali metals, elemental fluorine and fluorine precursors at elevated temperatures, and concentrated perchloric acid. It withstands temperatures from ⫺270⬚ to 250⬚C and may be sterilized repeatedly by all known chemical and thermal methods. 10.3.8.3

Perfluoroalkoxy Resin. Perfluoroalkoxy resin has the following formula:

It resembles polytetrafluoroethylene and fluorinated ethylene propylene in its chemical resistance, electrical properties, and coefficient of friction. Its strength, hardness, and wear resistance are about equal to the former plastic and superior to that of the latter at temperatures above 150⬚C. 10.3.8.4 Poly(vinylidene Fluoride). Poly(vinylidene fluoride) consists of linear chains in which the predominant repeating unit is [9 CH2 9CF2 9]n It has good weathering resistance and does not support combustion. It is resistant to most chemicals and solvents and has greater strength, wear resistance, and creep resistance than the preceding three fluorocarbon resins. 10.3.8.5 Poly(1-Chloro-1,2,2-Trifluoroethylene). Poly(1-chloro-1,2,2-trifluoroethylene consists of linear chains in which the predominant repeating unit is

It possesses outstanding barrier properties to gases, especially water vapor. It is surpassed only by the fully fluorinated polymers in chemical resistance. A few solvents dissolve it at temperatures

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above 100⬚C, and it is swollen by a number of solvents, especially chlorinated solvents. It is harder and stronger than perfluorinated polymers, and its impact strength is lower.

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10.3.8.6 Ethylene-Chlorotrifluoroethylene Copolymer. Ethylene-chlorotrifluoroethylene copolymer consists of linear chains in which the predominant 1 : 1 alternating copolymer is

This copolymer has useful properties from cryogenic temperatures to 180⬚C. Its dielectric constant is low and stable over a broad temperature and frequency range. 10.3.8.7 Ethylene-Tetrafluoroethylene Copolymer. Ethylene-tetrafluoroethylene copolymer consists of linear chains in which the repeating unit is [9CH2 9CH2 9CF2 9CF2 9 ]n Its properties resemble those of ethylene-chlorotrifluoroethylene copolymer. 10.3.8.8 Poly(vinyl Fluoride). Poly(vinyl fluoride) consists of linear chains in which the repeating unit is [9 CH2 9 CHF 9]n It is used only as a film, and it has good resistance to abrasion and resists staining. It also has outstanding weathering resistance and maintains useful properties from ⫺100 to 150⬚C. 10.3.9

Nitrile Resins

The principal monomer of nitrile resins is acrylonitrile (see “Polyacrylonitrile”), which constitutes about 70% by weight of the polymer and provides the polymer with good gas barrier and chemical resistance properties. The remainder of the polymer is 20 to 30% methylacrylate (or styrene), with 0 to 10% butadiene to serve as an impact-modifying termonomer.

10.3.10

Melamine Formaldehyde

The monomer used for preparing melamine formaldehyde is formed as follows:

Hexamethylolmelamine can further condense in the presence of an acid catalyst; ether linkages can also form (see “Urea Formaldehyde”). A wide variety of resins can be obtained by careful selection of pH, reaction temperature, reactant ratio, amino monomer, and extent of condensation. Liquid coating resins are prepared by reacting methanol or butanol with the initial methylolated products. These can be used to produce hard, solvent-resistant coatings by heating with a variety of hydroxy, carboxyl, and amide functional polymers to produce a cross-linked film.

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10.3.11 10.3.11.1

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Phenolics Phenol-Formaldehyde Resin. Phenol-formaldehyde resin is prepared as follows: C6H5OH ⫹ H2C"O : [ 9C6H2(OH)CH2 9]n

One-Stage Resins. The ratio of formaldehyde to phenol is high enough to allow the thermosetting process to take place without the addition of other sources of cross-links. Two-Stage Resins. The ratio of formaldehyde to phenol is low enough to prevent the thermosetting reaction from occurring during manufacture of the resin. At this point the resin is termed novolac resin. Subsequently, hexamethylenetetramine is incorporated into the material to act as a source of chemical cross-links during the molding operation (and conversion to the thermoset or cured state).

10.3.12

Polyamides

10.3.12.1 Nylon 6, 11, and 12. This class of polymers is polymerized by addition reactions of ring compounds that contain both acid and amine groups on the monomer.

Nylon 6 is polymerized from 2-oxohexamethyleneimine (6 carbons); nylon 11 and 12 are made this way from 11- and 12-carbon rings, respectively. 10.3.12.2 Nylon 6/6, 6/9, and 6/12. As illustrated below, nylon 6/6 is polymerized from 1,6hexanedioic acid (six carbons) and 1,6-hexanediamine (six carbons).

Other nylons are made this way from direct combinations of monomers to produce types 6/9, 6/10, and 6/12. Nylon 6 and 6/6 possess the maximum stiffness, strength, and heat resistance of all the types of nylon. Type 6/6 has a higher melt temperature, whereas type 6 has a higher impact resistance and better processibility. At a sacrifice in stiffness and heat resistance, the higher analogs of nylon are useful primarily for improved chemical resistance in certain environments (acids, bases, and zinc chloride solutions) and for lower moisture absorption. Aromatic nylons, [9NH 9 C6H4 9CO9 ]n (also called aramids), have specialty uses because of their improved clarity.

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Poly(amide-imide)

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Poly(amide-imide) is the condensation polymer of 1,2,4-benzenetricarboxylic anhydride and various aromatic diamines and has the general structure:

It is characterized by high strength and good impact resistance, and retains its physical properties at temperatures up to 260⬚C. Its radiation (gamma) resistance is good.

10.3.14

Polycarbonate

Polycarbonate is a polyester in which dihydric (or polyhydric) phenols are joined through carbonate linkages. The general-purpose type of polycarbonate is based on 2,2-bis(4⬘-hydroxybenzene)propane (bisphenol A) and has the general structure:

Polycarbonates are the toughest of all thermoplastics. They are window-clear, amazingly strong and rigid, autoclavable, and nontoxic. They have a brittleness temperature of ⫺135⬚C.

10.3.15

Polyester

10.3.15.1 Poly(butylene Terephthalate). Poly(butylene terephthalate) is prepared in a condensation reaction between dimethyl terephthalate and 1,4-butanediol and its repeating unit has the general structure

This thermoplastic shows good tensile strength, toughness, low water absorption, and good frictional properties, plus good chemical resistance and electrical properties. 10.3.15.2 Poly(ethylene Terephthalate). Poly(ethylene terephthalate) is prepared by the reaction of either terephthalic acid or dimethyl terephthalate with ethylene glycol, and its repeating unit has the general structure.

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The resin has the ability to be oriented by a drawing process and crystallized to yield a highstrength product. 10.3.15.3 Unsaturated Polyesters. Unsaturated polyesters are produced by reaction between two types of dibasic acids, one of which is unsaturated, and an alcohol to produce an ester. Double bonds in the body of the unsaturated dibasic acid are obtained by using maleic anhydride or fumaric acid. 10.3.15.4 PCTA Copolyester. Poly(1,4-cyclohexanedimethylene terephthalic acid) (PCTA) copolyester is a polymer of cyclohexanedimethanol and terephthalic acid, with another acid substituted for a portion of the terephthalic acid otherwise required. It has the following formula:

10.3.15.5

Polyimides.

Polyimides have the following formula:

They are used as high-temperature structural adhesives since they become rubbery rather than melt at about 300⬚C.

10.3.16

Poly(methylpentene)

Poly(methylpentene) is obtained by a Ziegler-type catalytic polymerization of 4-methyl-1-pentene. Its key properties are its excellent transparency, rigidity, and chemical resistance, plus its resistance to impact and to high temperatures. It withstands repeated autoclaving, even at 150⬚C.

10.3.17

Polyolefins

10.3.17.1 Polyethylene. Polymerization of ethylene results in an essentially straight-chain highmolecular-weight hydrocarbon. CH2 "CH2 : [9 CH2 9 CH2 9]n Branching occurs to some extent and can be controlled. Minimum branching results in a “highdensity” polyethylene because of its closely packed molecular chains. More branching gives a less compact solid known as “low-density” polyethylene.

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A key property is its chemical inertness. Strong oxidizing agents eventually cause some oxidation, and some solvents cause softening or swelling, but there is no known solvent for polyethylene at room temperature. The brittleness temperature is ⫺100⬚C for both types. Polyethylene has good low-temperature toughness, low water absorption, and good flexibility at subzero temperatures.

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10.3.17.2 Polypropylene. The polymerization of propylene results in a polymer with the following structure:

The desired form in homopolymers is the isotactic arrangement (at least 93% is required to give the desired properties). Copolymers have a random arrangement. In block copolymers a secondary reactor is used where active polymer chains can further polymerize to produce segments that use ethylene monomer. Polypropylene is translucent and autoclavable and has no known solvent at room temperature. It is slightly more susceptible to strong oxidizing agents than polyethylene. 10.3.17.3 Polybutylene. Polybutylene is composed of linear chains having an isotactic arrangement of ethyl side groups along the chain backbone.

It has a helical conformation in the stable crystalline form. Polybutylene exhibits high tear, impact, and puncture resistance. It also has low creep, excellent chemical resistance, and abrasion resistance with coilability. 10.3.17.4 Ionomer. Ionomer is the generic name for polymers based on sodium or zinc salts of ethylene-methacrylic acid copolymers in which interchain ionic bonding, occurring randomly between the long-chain polymer molecules, produces solid-state properties. The abrasion resistance of ionomers is outstanding, and ionomer films exhibit optical clarity. In composite structures ionomers serve as a heat-seal layer.

10.3.18

Poly(phenylene Sulfide)

Poly(phenylene sulfide) has the following formula:

The recurring para-substituted benzene rings and sulfur atoms form a symmetrical rigid backbone. The high degree of crystallization and the thermal stability of the bond between the benzene ring and sulfur are the two properties responsible for the polymer’s high melting point, thermal stability, inherent flame retardance, and good chemical resistance. There are no known solvents of poly(phenylene sulfide) that can function below 205⬚C.

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10.3.19 10.3.19.1 cyanates.

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Polyurethane

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Foams. Polyurethane foams are prepared by the polymerization of polyols with iso-

Commonly used isocyanates are toluene diisocyanate, methylene diphenyl isocyanate, and polymeric isocyanates. Polyols used are macroglycols based on either polyester or polyether. The former [poly(ethylene phthalate) or poly(ethylene 1,6-hexanedioate)] have hydroxyl groups that are free to react with the isocyanate. Most flexible foam is made from 80/20 toluene diisocyanate (which refers to the ratio of 2,4-toluene diisocyanate to 2,6-toluene diisocyanate). High-resilience foam contains about 80% 80/20 toluene diisocyanate and 20% poly(methylene diphenyl isocyanate), while semiflexible foam is almost always 100% poly(methylene diphenyl isocyanate). Much of the latter reacts by trimerization to form isocyanurate rings. Flexible foams are used in mattresses, cushions, and safety applications. Rigid and semiflexible foams are used in structural applications and to encapsulate sensitive components to protect them against shock, vibration, and moisture. Foam coatings are tough, hard, flexible, and chemically resistant. 10.3.19.2 Elastomeric Fiber. Elastomeric fibers are prepared by the polymerization of polymeric polyols with diisocyanates.

The structure of elastomeric fibers is similar to that illustrated for polyurethane foams.

10.3.20

Silicones

Silicones are formed in the following multistage reaction:

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The silanols formed above are unstable and under dehydration. On polycondensation, they give polysiloxanes (or silicones) which are characterized by their three-dimensional branched-chain structure. Various organic groups introduced within the polysiloxane chain impart certain characteristics and properties to these resins.

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Methyl groups impart water repellency, surface hardness, and noncombustibility. Phenyl groups impart resistance to temperature variations, flexibility under heat, resistance to abrasion, and compatibility with organic products. Vinyl groups strengthen the rigidity of the molecular structure by creating easier cross-linkage of molecules. Methoxy and alkoxy groups facilitate cross-linking at low temperatures. Oils and gums are nonhighly branched- or straight-chain polymers whose viscosity increases with the degree of polycondensation.

10.3.21 10.3.21.1

Styrenics Polystyrene. Polystyrene has the following formula:

Polystyrene is rigid with excellent dimensional stability, has good chemical resistance to aqueous solutions, and is an extremely clear material. Impact polystyrene contains polybutadiene added to reduce brittleness. The polybutadiene is usually dispersed as a discrete phase in a continuous polystyrene matrix. Polystyrene can be grafted onto rubber particles, which assures good adhesion between the phases. 10.3.21.2 Acrylonitrile-Butadiene-Styrene (ABS) Copolymers. This basic three-monomer system can be tailored to yield resins with a variety of properties. Acrylonitrile contributes heat resistance, high strength, and chemical resistance. Butadiene contributes impact strength, toughness, and retention of low-temperature properties. Styrene contributes gloss, processibility, and rigidity. ABS polymers are composed of discrete polybutadiene particles grafted with the styrene-acrylonitrile copolymer; these are dispersed in the continuous matrix of the copolymer. 10.3.21.3 Styrene-Acrylonitrile (SAN) Copolymers. SAN resins are random, amorphous copolymers whose properties vary with molecular weight and copolymer composition. An increase in molecular weight or in acrylonitrile content generally enhances the physical properties of the copolymer but at some loss in ease of processing and with a slight increase in polymer color. SAN resins are rigid, hard, transparent thermoplastics which process easily and have good dimensional stability— a combination of properties unique in transparent polymers.

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Sulfones

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Below are the fomulas for three polysulfones.

The isopropylidene linkage imparts chemical resistance, the ether linkage imparts temperature resistance, and the sulfone linkage imparts impact strength. The brittleness temperature of polysulfones is ⫺100⬚C. Polysulfones are clear, strong, nontoxic, and virtually unbreakable. They do not hydrolyze during autoclaving and are resistant to acids, bases, aqueous solutions, aliphatic hydrocarbons, and alcohols. 10.3.23

Thermoplastic Elastomers

10.3.23.1 Polyolefins. In these thermoplastic elastomers the hard component is a crystalline polyolefin, such as polyethylene or polypropylene, and the soft portion is composed of ethylene-propylene rubber. Attractive forces between the rubber and resin phases serve as labile cross-links. Some contain a chemically cross-linked rubber phase that imparts a higher degree of elasticity. 10.3.23.2 Styrene-Butadiene-Styrene Block Copolymers. Styrene blocks associate into domains that form hard regions. The midblock, which is normally butadiene, ethylene-butene, or isoprene blocks, forms the soft domains. Polystyrene domains serve as cross-links. 10.3.23.3 Polyurethanes. The hard portion of polyurethane consists of a chain extender and polyisocyanate. The soft component is composed of polyol segments. 10.3.23.4 Polyesters. The hard portion consists of copolyester, and the soft portion is composed of polyol segments. 10.3.24

Vinyl

10.3.24.1 Poly(vinyl Chloride) (PVC). Polymerization of vinyl chloride results in the formation of a polymer with the following formula:

When blended with phthalate ester plasticizers, PVC becomes soft and pliable. Its key properties are good resistance to oils and a very low permeability to most gases.

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10.21

Poly(vinyl Acetate). Poly(vinyl acetate) has the following formula:

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Poly(vinyl acetate) is used in latex water paints because of its weathering, quick-drying, recoatability, and self-priming properties. It is also used in hot-melt and solution adhesives. 10.3.24.3

Poly(vinyl Alcohol). Poly(vinyl alcohol) has the following formula:

It is used in adhesives, paper coating and sizing, and textile warp size and finishing applications. 10.3.24.4 tion:

Poly(vinyl Butyral). Poly(vinyl butyral) is prepared according to the following reac-

Its key characteristics are its excellent optical and adhesive properties. It is used as the interlayer film for safety glass. 10.3.24.5 Poly(vinylidene Chloride). Poly(vinylidene chloride) is prepared according to the following reaction: CH2 " CCl2 ⫹ CH2 "CHCl : [ 9CH2 9CCl2 9CH2 9 CHCl9]n Random copolymer

10.3.25

Urea Formaldehyde

The reaction of urea with formaldehyde yields the following products, which are used as monomers in the preparation of urea formaldehyde resin. H2N9CO9NH2 ⫹ H2CO : H2N9CO9NH9CH2OH ⫹ HOCH2 9NH9 CO9 NH9CH2OH The reaction conditions can be varied so that only one of those monomers is formed. 1-Hydroxymethylurea and 1,3-bis(hydroxymethyl)urea condense in the presence of an acid catalyst to produce urea formaldehyde resins. A wide variety of resins can be obtained by careful selection of the pH, reaction temperature, reactant ratio, amino monomer, and degree of polymerization. If the reaction is carried far enough, an infusible polymer network is produced. Liquid coating resins are prepared by reacting methanol or butanol with the initial hydroxymethylureas. Ether exchange reactions between the amino resin and the reactive sites on the polymer produce a cross-linked film.

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TABLE 10.2 Properties of Commercial Plastics Acetal

Properties

175

175

181

175

181

1.42 0.25– 0.40 19.7

1.41 0.22 19.7

1.56 0.25 19.3

1.61 0.29 22.8

1.54 0.20 15.7

1015 3.7 3.7

1015 3.7 3.7

5 ⫻ 1014 3.9 3.9

3 ⫻ 1016 3.1 3.1

0.005

0.005

0.005

0.005

670

450

10.22

INTERACTIVE

Mechanical Compressive modulus, 103 lb · in⫺2

21% poly(tetrafluoroethylene)filled homopolymer

ROTATED

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz)

Copolymer

25% glassreinforced copolymer

LEFT

Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, KV · mm⫺1

Homopolymer

20% glassreinforced homopolymer

TABLE 10.2 Properties of Commercial Plastics (Continued) Acetal

Compressive strength, rupture or 1% yield, 103 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

21% poly(tetrafluoroethylene)filled homopolymer

5.29 25– 75

16 (10% yield) 40– 75

18 (10% yield) 7

17 (10% yield) 3

13 (10% yield) 15– 22

380– 430

375

730

1100

340– 350

14 M94

13 M78

15 M90

28 M79

M78

69– 123 520

53– 80 410

43 1000

96 1250

37– 64

10

10

8.5

18.5

7.6

9.5– 12

8.5

Homopolymer

6.9– 7.6

27.9 100

85

36– 81

124

110

157

84 0.35 0.23

0.23

75 163

100

RIGHT

Thermal Burning rate, mm · min⫺1 Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K⫺1

Copolymer

25% glassreinforced copolymer

DEAN 37261 (McGHP)

Properties

20% glassreinforced homopolymer

ROTATED

10.23

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DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Alloy Acrylic

Properties

Heatresistant

90– 105

90– 105

80– 100

100– 125

1.17– 1.20 0.1– 0.4 15.7– 19.9

1.18– 1.20 0.2– 0.4 17.7– 21.7

1.11– 1.18 0.2– 0.8 15.0– 19.9

1.16– 1.19 0.2– 0.3 15.7– 19.9

⬎1014 3.3– 4.5

⬎1014 3.5– 4.5 3.0– 3.5 0.04– 0.06 0.02– 0.03

370– 460

390– 475

Alkyd, molded

Acrylic poly(vinyl chloride) alloy

105 2.22– 2.24 0.06 ⬎15.7

3.8– 5.0 3.6– 4.7 0.012– 0.026 0.01– 0.016

240– 370

350– 460

19.7

330– 400

INTERACTIVE

Mechanical Compressive modulus, 10 4 lb · in⫺2

Impactmodified

ROTATED

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

Cast sheet

LEFT

Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, KV · mm⫺1

Poly(methyl methacrylate)

Acrylonitrilebutadienestyrenepoly(vinyl chloride) alloy

10.24

TABLE 10.2 Properties of Commercial Plastics (Continued) Alloy Acrylic

Properties

Impactmodified

Heatresistant

12– 18 2– 10

11– 19 2– 7

4– 14 20– 70

17 3– 5

420– 460

390– 475

200– 380

460– 500

13– 19 M85– M105

12– 17 M80– M100

7– 13 R105– R120

12– 16 M95– M105

16– 27 380– 450

16– 21 350– 450

43– 133 200– 400

16– 21 350– 460

7– 11

8– 11

5– 9

10

Thermal Burning rate, mm · min⫺1

0.5– 2.2

Alkyd, molded 16– 20

Acrylic poly(vinyl chloride) alloy 8.4 100 330– 400

340

10.7 R99– R105

9.6 R100

27– 240

800 330– 335

560 330

4.5– 6.5 10– 13

6.5

5.8

E76

Selfextinguishing

50– 90

50– 90

50– 80

50– 60

40– 55

74– 99

71– 102

74– 95

88– 104

177– 204

0.36

60– 71 0.35

0.17– 0.25

0.17– 0.25

46 71

220

0.17– 0.21

0.19

RIGHT

Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1, K ⫺1

Cast sheet

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Poly(methyl methacrylate)

Acrylonitrilebutadienestyrenepoly(vinyl chloride) alloy

ROTATED

10.25

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Allyl

Alloy

Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

150 1.12– 1.20 0.21– 0.24 17.7

Allyl-diglycolcarbonate polymer

Mineral-filled

Thermoset

Thermoset

Thermoset

230

230

140

1.3– 1.4 0.2 15.0

1.7– 2.0 0.12– 0.35 15.7– 17.7

1.65– 1.85 0.2– 0.5 15.7– 17.7

1.27– 1.34 2– 7 11– 24

1.29– 1.34 1.7– 6.5 9– 24

1.15– 1.22 0.9– 2.2 9– 18

1010 – 1013 3.4– 7.4 3.2– 7.0

1010 – 1013 3.5– 7.5 3.2– 7.0

1010 – 1012 3.7– 4.3 3.3– 3.8

0.01– 0.06 0.01– 0.06

0.01– 0.06 0.01– 0.10

0.01– 0.04 0.01– 0.04

Molding

Sheet

10.26

INTERACTIVE

300

Sheet

ROTATED

Glass-filled

Electrical Volume (dc) resistivity, ohmcm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz) Mechanical Compressive modulus, 10 3 lb · in⫺2

Cellulose acetate

Diallyl phthalate molding

Celluloseacetatebutyrate resin

LEFT

Properties

Polycarbonate acrylonitrilebutadienestyrene alloy

Cellulosic

TABLE 10.2 Properties of Commercial Plastics (Continued) Alloy

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

11 10– 15

21– 23

300– 400

Diallyl phthalate molding Glass-filled

Mineral-filled

Cellulose acetate Sheet

25– 36 6– 40

Sheet

25– 35 3– 5

20– 32 3– 5

250– 330

1200– 1500

1000– 1400

13.0– 13.7 R117

6– 13 M95– M100

9– 20 E80– E87

8.5– 11 E61

6– 10 R85– R120

2– 16 R100– R123

4– 9 R50– R95

560 370– 380

11– 21 300

21– 800 1400– 2200

16– 43 1200– 2200

107– 454

53– 214

133– 288 200– 250

7.0– 7.3

5– 6

6– 11

5– 8

4.5– 8.0

1.9– 9.0

2.6– 6.9

2.2– 7.4

4.1– 7.6

8.5

22– 33 17– 40

Molding

50– 100 740– 1300

1.3– 3.8

1.3– 3.8

63– 67

5.4– 9.6

0.68– 2.4

2.8

100– 150

80– 180

110– 170

104– 116

60– 88

165– 288⫹

160– 288

44– 91

51– 98

49– 58

0.3– 0.4

0.3– 0.42

0.3– 0.4

0.17– 0.34

0.17– 0.34

0.17– 0.34

0.25– 0.38

0.20– 0.21

0.21– 0.63

0.30– 1.04

RIGHT

Thermal Burning rate, mm · min⫺1 Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K⫺1

Allyl-diglycolcarbonate polymer

Celluloseacetatebutyrate resin

DEAN 37261 (McGHP)

Properties

Polycarbonate acrylonitrilebutadienestyrene alloy

Cellulosic

Allyl

ROTATED

10.27

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Epoxy

Cellulosic

Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

Bisphenol Ethyl cellulose

140

190

135

1.15– 1.22 0.9– 2.2 9– 13

1.17– 1.24 1.2– 2.8 12– 17.7

1.09– 1.17 0.8– 1.8 13.8– 19.7

1010 – 1012 3.5– 6.4 3.2– 6.2

3.01

Cellulose nitrate

1.35– 1.40

Chlorinated polyether

Glass-fiberreinforced

Mineralfilled

125

Thermoset

Thermoset

1.4

1.6– 2.0 0.04– 0.20 9.8– 15.7

1.6– 2.1 0.03– 0.20 9.8– 15.7

1010 7.0– 7.5 6.6

0.01– 0.04 0.01– 0.04

3000

ROTATED

Mechanical Compressive modulus, 10 3 lb · in⫺2

Celluloseacetate propionate resin, molding

LEFT

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

Celluloseacetate butyrate resin, molding

INTERACTIVE

10.28

TABLE 10.2 Properties of Commercial Plastics (Continued) Epoxy

Cellulosic

Properties

Thermal Burning rate, mm · min⫺1

Bisphenol Ethyl cellulose

Cellulose nitrate

Glass-fiberreinforced

Mineralfilled

18,000– 40,000 4

18,000– 40,000

2.1– 7.5 40– 88

2.4– 7.0 29– 100

90– 300

120– 350

1.8– 9.3 R31– R116

2.9– 11.4 R10– R122

4– 12 R50– R115

9– 11 R95– R115

5 R100

8– 30 M100– M112

6– 18 M100– M112

53– 582 50– 200

27 to no break 60– 215

21

267– 374 190– 220

21

16– 533 3

16– 22

2.6– 6.9

2.0– 7.8

2– 8

7– 8

1.5– 1.8

5– 20

4– 10

5– 40

2.1– 8.0 40– 45

Chlorinated polyether

600– 800

2– 4.5

1.3– 3.8

Selfextinguishing

110– 170

110– 170

100– 200

80– 120

6.6

11– 50

20– 60

44– 94

44– 109

45– 88

60– 71

185

107– 260

107– 260

0.17– 0.42

0.17– 1.48

255 0.3– 0.4 0.17– 0.30

0.31– 0.41 0.17– 0.30

0.16– 0.30

0.23

RIGHT

Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

Celluloseacetate propionate resin, molding

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Celluloseacetate butyrate resin, molding

ROTATED

10.29

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Epoxy Casting resin Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

Poly(chlorotrifluoroethylene)

Flexible

Mineral-filled

Thermoset

Thermoset

Thermoset

327

327

220

310

1.11– 1.40 0.08– 0.15 11.8– 19.7

1.05– 1.35 0.27– 0.50 9.3– 15.8

1.7– 2.1 0.05– 0.2 11.8– 13.8

2.14– 2.20 0.01 18.9

2.2– 2.3

2.1– 2.2 0.03 19.7– 23

2.12– 2.17

1012 – 1017 3.5– 5.0 3.5– 5.0

Granular

Glass-fiberreinforced

12.6

1018 2.1 2.1

1018 2.3– 2.7 2.3– 2.5

0.0002 0.0002

0.001 0.005

60

Perfluoroalkoxy

19.7

ROTATED

Mechanical Compressive modulus, 10 3 lb · in⫺2

Poly(tetrafluoroethylene)

Novolac resin

LEFT

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

Unfilled

Fluorocarbon

INTERACTIVE

10.30

TABLE 10.2 Properties of Commercial Plastics (Continued) Epoxy Casting resin

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10⫺3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Unfilled 15– 25 3– 6

Flexible 1– 14 20– 70

Novolac resin Mineral-filled

Granular

Glass-fiberreinforced

Poly(chlorotrifluoroethylene)

30 2– 4

1.7 200– 400

200– 300

4.6– 7.4 80– 250

2000

80

235

120

(D50– D55)

2 (D60– D70)

7.4– 9.3 R75– R95

16– 20

Perfluoroalkoxy

300

13– 21 M80– M110

1– 13

10.7– 53 350

187– 267 1– 350

21

160 58– 80

144

133– 160 150– 300

No break

4– 13

2– 10

6– 12

2– 5

2– 2.7

4.5– 6

4– 4.3

Selfextinguishing

Selfextinguishing

Selfextinguishing

77– 100

70

(D64)

30

Thermal Burning rate, mm · min⫺1

45– 65

20– 100

22– 30

100

46– 288

23– 121

149– 260

121 (66 lb · in⫺2 )

126 (66 lb · in⫺2 )

260 0.25

200 0.22

0.17– 0.21

0.25

0.34– 0.40

0.19– 0.22

74 (66 lb · in⫺2 )

0.25

RIGHT

Coefficient of linear thermal expansion, 10⫺6⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K⫺1

Poly(tetrafluoroethylene)

DEAN 37261 (McGHP)

Properties

Fluorocarbon

ROTATED

10.31

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Fluorocarbon

Melamine formaldehyde

Ethylene-tetrafluoroethylene copolymer Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

Unfilled

Glass-fiberreinforced

Cellulosefilled

Glass-fiberreinforced

275

156

270

270

245

Thermoset

Thermoset

2.14– 2.17 ⬍0.01 20– 24

1.75– 1.78 0.04– 0.06 10

1.7 0.03 16

1.8 0.02 17

1.68 0.01 19

1.47– 1.52 0.1– 0.8 11– 16

1.5– 2.0 0.09– 1.3 5– 15

2.1 2.1

8– 9 8– 9

2.6 2.6

2.6 2.6

ROTATED

Mechanical Compressive modulus, 10 3 lb · in⫺2

Poly(vinylidene fluoride)

Ethylenechlorotrifluoroethylene copolymer

LEFT

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

Fluorinated ethylenepropylene resin

High High

120

120

1200

240

INTERACTIVE

10.32

TABLE 10.2 Properties of Commercial Plastics (Continued) Fluorocarbon

Melamine formaldehyde

Ethylene-tetrafluoroethylene copolymer Properties

Thermal Burning rate, mm · min⫺1

Unfilled

Glass-fiberreinforced

Cellulosefilled

Glass-fiberreinforced

2.2 250– 330

8.7– 10 25– 500

7.1 100– 400

10 8

200– 300

33– 45 0.6– 1.0

80– 95

200

200

950

240

1100

(D60– D65)

8.6– 11 (D80)

5.5 R50 (D75)

10.7 R74

7 R95

9– 16 M115– M125

14– 23 M115

No break 50

192– 214 120

No break 120

480 1200

No break 240

11– 21 1.1– 1.4

32– 961 1.6– 2.4

2.7– 3.1

5.5– 7.4

6.5

12

7

5– 13

5– 10.5

Not combustible

Not combustible

Selfextinguishing

Selfextinguishing

Not combustible

Not combustible

Not combustible

20– 35 0.6

83– 105

85

59

10– 32

80

40– 45

15– 28

70 (66 lb · in⫺2 )

80– 90

71

210

77

177– 199

190– 204

205 0.28

150

0.25

0.19– 0.24

210

0.24

0.16

0.27– 0.41

0.41– 0.49

RIGHT

Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K⫺1

Poly(vinylidene fluoride)

Ethylenechlorotrifluoroethylene copolymer

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Fluorinated ethylenepropylene resin

ROTATED

10.33

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued)

Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

Mechanical Compressive modulus, 10 3 lb · in⫺2

Nitrile

Thermoset 1.5– 1.7 0.3– 0.65 8.7– 12.8

95 1.15 0.28 8.7– 9.5

1.9 ⫻ 1015

Unfilled

Woodflourfilled

Glass-fiberreinforced

Cellulosefilled

Mineralfilled

Thermoset

Thermoset

Thermoset

Thermoset

Thermoset

1.24– 1.32 0.1– 0.36 9.8– 15.8

1.37– 1.46 0.3– 1.2 10.2– 15.8

1.69– 2.0 0.03– 1.2 5.5– 15.8

1.38– 1.42 0.5– 0.9 11.8– 15

1.42– 1.84 0.1– 0.3 7.9– 13.8

1 ⫻ 1012 to 7 ⫻ 1012 6.5– 7.5 4.0– 5.5 0.10– 0.15 0.04– 0.05

ROTATED

Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

Phenolic

LEFT

Electrical Volume (dc) resistivity, ohm-cm

Melamine phenolic, woodflour- and cellulosefilled

INTERACTIVE

10.34

TABLE 10.2 Properties of Commercial Plastics (Continued)

Properties

Phenolic

Nitrile

Woodflourfilled

Glass-fiberreinforced

Cellulosefilled

Mineralfilled

26– 30 0.4– 0.8

12 3– 4

18– 32 1.5– 2.0

25– 31 0.4– 0.8

26– 70 0.2

22– 31 1– 2

22.5– 34.6 0.1– 0.5

1000– 2000

500– 590

700– 1500

1000– 1200

2000– 33,000

900– 1300

1000– 2000

8– 10 E95– E100

14 M72– M76

11– 17 M93– M120

7– 14 M100– M115

15– 60 E54– E101

5.5– 11 M95– 115

11– 14 E88

11– 21 800– 1700

80– 256 510– 580

13– 21 700– 1500

11– 32 800– 1700

27– 960 1900– 3300

21– 59

14– 19 2400

6– 8

9

6– 9

5– 9

7– 18

3.5– 6.5

6– 9.7

12– 15

Thermal Burning rate, mm · min⫺1

Selfextinguishing 10– 40

66

68

30– 45

8– 21

20– 31

19– 26

140– 154

73

74– 80

149– 188

177– 316

149– 177

320– 246

0.17– 0.30

0.26

0.15

0.17– 0.34

0.34– 0.59

0.25– 0.38

0.42– 0.57

RIGHT

Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K⫺1

Unfilled

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Melamine phenolic, woodflour- and cellulosefilled

ROTATED

10.35

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Polyamide Nylon 6

Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

High-impact copolymer

Molding

33% glassfiberreinforced

Molybdenum disulfidefilled

Nylon 6/6nylon 6 copolymer

216

216

216

265

265

265

240

1.12– 1.14 2.9 15.8

1.35– 1.42 1.2 15.8

1.08– 1.17 1.3– 1.5 22

1.13– 1.15 1.0– 1.3 24

1.38 1.0

1.15– 1.17 0.8– 1.1 14

1.08– 1.14 1.5– 2.0 15.8

1012 9.8 3.7

1012 – 1015 4.0 3.6

1010 16 4

0.14 0.12

0.01– 0.02 0.02– 0.03

0.4 0.1

ROTATED

Mechanical Compressive modulus, 10 3 lb · in⫺2

30– 35% glass-fiberreinforced

LEFT

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

Molding and extrusion

Nylon 6/6

250

INTERACTIVE

10.36

TABLE 10.2 Properties of Commercial Plastics (Continued) Polyamide Nylon 6

Properties

Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2 Thermal Burning rate, mm · min⫺1

High-impact copolymer

Molding

33% glassfiberreinforced

Molybdenum disulfidefilled

Nylon 6/6nylon 6 copolymer

13– 16 30– 100

19 3– 6

150– 270

15 (yield) 60

24.9 3

12.5 15

40

390

1500

110– 320

420

1300

450

150– 410

14 R119

33 M101

5– 12 R81– R110

17 R120

41 M100

17 R119

R119

32– 53

160

96 to no break

43– 53

117

240

37

380

1450

550

150– 410

11.8

25

28

13.7

7.4– 12.4

Selfextinguishing

7.5– 11

8

12 8

Selfextinguishing

Selfextinguishing

Selfextinguishing

Selfextinguishing

Selfextinguishing

Selfextinguishing

80– 90

20– 30

30– 40

80

15– 20

54

68– 85

210

45– 54

75

249

127

107 0.4 0.24

135 0.4 0.24

0.24

0.22

77

RIGHT

Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

30– 35% glass-fiberreinforced

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1

Molding and extrusion

Nylon 6/6

ROTATED

10.37

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Polyamide Nylon 6/12

Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

Nylon 11, molding and extrusion

Nylon 12, molding and extrusion

Aromatic nylon (aramid), molded and unfilled

Poly(amideimide), unfilled

205

217

217

194

179

275

1.08– 1.10 0.5 24

1.06– 1.08 0.4 16

1.31– 1.38 0.2 21

1.03– 1.05 0.3 17

1.01– 1.02 0.25 18

1.30 0.6 31

275 1.40 0.28 24

290

413

1015 4.0 3.5

1014 3.8 3.0

0.02 0.02

0.07 0.04

180

ROTATED

Mechanical Compressive modulus, 10 3 lb · in⫺2

Molding

30– 35% glass-fiberreinforced

LEFT

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

Nylon 6/9, molding and extrusion

INTERACTIVE

10.38

TABLE 10.2 Properties of Commercial Plastics (Continued) Polyamide Nylon 6/12

Properties

Molding

30– 35% glass-fiberreinforced

Nylon 11, molding and extrusion

Nylon 12, molding and extrusion

Poly(amideimide), unfilled

1125

2.4 150

4

300

7.5 300

30 5

40 12– 18

290

290

1120

150

165

640

664

R111

R114

E40– E50

R108

1.5 R106– R109

25.8 E90

30 E78

59 275

53 290

139 1200

96 185

107– 300 180

75

133 730

8.5

8.8

24

8

8– 9

17.5

26.9

55– 100

67– 100

40

36

54

54

260

274

8.8

Thermal Burning rate, mm · min⫺1

Selfextinguishing 90

57– 60

82

93– 218

0.4

100– 120 0.58

0.22

0.34

260

0.22

0.22

0.25

RIGHT

Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K⫺1

Aromatic nylon (aramid), molded and unfilled

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Nylon 6/9, molding and extrusion

ROTATED

10.39

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Polycarbonate

Thermoplastic polyester Poly(butylene terephthalate)

Properties

Poly(aryl ether), unfilled

Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

160 1.14 0.25 17

150 1.4 0.14 19

2 ⫻ 1016 3.17 2.96

⬎1016 3.35 3.31

0.0009 0.010

0.011 0.007

350

1300

30% glass-fiberreinforced

Unfilled

30% glass-fiberreinforced

232– 267

232– 267

245

245

1.31– 1.38 0.08– 0.09 16– 22

1.52 0.06– 0.08 18– 22

1.34– 1.39 0.1– 0.2

1.27 0.05 22

1016

1016 3.25

ROTATED

Mechanical Compressive modulus, 10 3 lb · in⫺2

140 1.2 0.15 15

Unfilled

Poly(ethylene terephthalate)

LEFT

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

Low viscosity

30% glassfiber reinforced

INTERACTIVE

10.40

TABLE 10.2 Properties of Commercial Plastics (Continued) Polycarbonate

Thermoplastic polyester Poly(butylene terephthalate)

Properties

Unfilled

30% glass-fiberreinforced

Poly(ethylene terephthalate)

Unfilled

30% glass-fiberreinforced

80

12.5 110

18 3– 5

8.6– 14.5 50– 300

18– 23.5 2– 4

11– 15 50– 300

25 3

300

340

1100

330– 400

1100– 1200

35– 450

1440

11 R117

13.5 M70

23 M92

12– 16.7 M68– M78

26– 29 M90

14– 18 M94– M101

33.5 M100

427 320

14 345

107 1250

43– 53 280

69– 85 1300

13– 32 400– 600

101 1440

7.5

9.5

19

8.2

17– 19

8.5– 10.5

23

9.0

Thermal Burning rate, mm · min⫺1

Selfextinguishing

Selfextinguishing

65

68

22

60– 95

25

65

29

149

138– 145

146

50– 85

220

38– 41

224

143 0.3 0.30

0.20

0.27 0.22

0.18– 0.30

0.30

0.15

RIGHT

Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

Low viscosity

30% glassfiber reinforced

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Poly(aryl ether), unfilled

ROTATED

10.41

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Thermosetting and alkyd polyester

Thermoplastic polyester Aromatic polyester

Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

Extrusiontransparent

Injection molding

Unsaturated polyester

Alkyd molding compounds

Styrene-maleic acid copolymer, low-shrink

Butadienemaleic acid copolymer

Putty, mineral-filled

Glass-fiberreinforced

Thermoset

Thermoset

Thermoset

Thermoset

81

310– 365 1.36– 1.43 0.24 22

1.39 0.01 14

⬎1016

LEFT

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

3– 4

ROTATED

Mechanical Compressive modulus, 10 3 lb · in⫺2

Polyimide, unfilled

2000– 3000

INTERACTIVE

10.42

TABLE 10.2 Properties of Commercial Plastics (Continued) Thermoplastic polyester

Thermosetting and alkyd polyester

Aromatic polyester

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Styrene-maleic acid copolymer, low-shrink

225

10 7– 10

15– 30 3– 5

290

700

1000– 2500

10.6 R105

12

9– 35 40– 70 (Barcol)

300 11

101

6

Butadienemaleic acid copolymer 14– 30

Putty, mineral-filled

Glass-fiberreinforced

12– 38

15– 36

30– 40 8– 10

2000

2000

450– 500

16– 24 50– 60 (Barcol)

6– 17 E98

8.5– 26 E95

19– 28.8 E52– E99

133– 800 1000– 2500

214– 694 1500– 2500

16– 27 500– 3000

27– 854

80 300

4.5– 20

5– 10

3– 9

4– 9.5

10.5– 17.1

7

63

Polyimide, unfilled

12.5

29

6– 30

282

190– 260

160– 177

20– 50

15– 33

45– 56

177– 260

204– 260

277– 360

0.27 0.29

0.76– 0.93

0.51– 0.89

0.6– 0.89

0.10– 0.11

RIGHT

Thermal Burning rate, mm · min⫺1 Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

Injection molding

Alkyd molding compounds

DEAN 37261 (McGHP)

Properties

Extrusiontransparent

Unsaturated polyester

ROTATED

10.43

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Polyolefin Polyethylene

Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

Poly(methyl pentene), unfilled

Medium-density

High-density

95– 130 0.910– 0.925 ⬍0.01 18– 39

120– 140 0.926– 0.94 ⬍0.01 18– 39

120– 140 0.941– 0.965 ⬍0.01 18– 39

125– 135 0.94 ⬍0.01 28

⬎1015 2.3 2.3

⬎1015 2.3 2.3

⬍1015 2.3 2.3

⬍0.0005 ⬍0.0005

⬍0.0005 ⬍0.0005

⬍0.0005 ⬍0.0005

Glass-fiberreinforced, high-density

120– 140 1.28 0.02 20

230– 240 0.84 0.01

65– 90 0.92– 0.95 0.05– 0.13 24– 30

ROTATED

114– 171

Ethylenevinyl acetate copolymer

LEFT

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz) Mechanical Compressive modulus, 10 3 lb · in⫺2

Low-density

Ultra highmolecularweight

INTERACTIVE

10.44

TABLE 10.2 Properties of Commercial Plastics (Continued) Polyolefin Polyethylene

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield, strength, 10 3 lb · in⫺2

Medium-density

High-density

Glass-fiberreinforced, high-density

Ethylenevinyl acetate copolymer

5– 6.6 10– 50

90– 800

50– 600

2.7– 3.6 20– 130

450– 525

7 1.5

550– 900

110– 260

8– 60

60– 115

100– 260

130– 140

800

1– 20

4– 6.5 L67– L74

(D40– D51)

(D50– D60)

R30– R50

R50

11 R75

16– 64 160– 280

No break 14– 38

27– 854 25– 55

27– 1068 60– 180

No break

59

No break 20– 120

3.5– 4

0.6– 2.3

1.2– 3.5

3.1– 5.5

5.6

9

1.4– 2.8

0.8– 1.2

1.0– 2.2

3– 4

3.1– 4.0

1.0

1.0

1.0

117

100– 200

140– 160

110– 130

130

48

160– 200

41

32– 41

41– 49

43– 54

43– 49

121

34

175

70 0.55

93 0.55

200 0.46– 0.55

0.17

0.34

0.34– 0.42

0.46– 0.51

0.46

RIGHT

Thermal Burning rate, mm · min⫺1 Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

Low-density

Ultra highmolecularweight

DEAN 37261 (McGHP)

Properties

Poly(methyl pentene), unfilled

ROTATED

10.45

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Polyolefin

Poly(phenylene sulfide)

Polypropylene

Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h),% Dielectric strength, kV · mm⫺1

168

160– 168

0.91– 0.925 0.01– 0.02 18

0.90– 0.91 0.01– 0.03 24

0.89– 0.905 0.03 24

0.90 ⬍0.03 24

1017 2.2– 2.6 2.2– 2.6

1017 2.3 2.3

1017 2.3

⬍0.0005 0.0005– 0.002

0.0001– 0.0005 0.0001– 0.0002

0.0003

31

150– 300

Polyallomer

40% glass-fiberreinforced

120– 135

290

290

0.90 ⬍0.01 31

1.3 ⬍0.02 15

1.6 0.05 18

ROTATED

126

Copolymer

Injection molding

LEFT

Homopolymer

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz) Mechanical Compressive modulus, 10 3 lb · in⫺2

Impact copolymer

Polybutylene extrusion

INTERACTIVE

10.46

TABLE 10.2 Properties of Commercial Plastics (Continued) Polyolefin

Poly(phenylene sulfide)

Polypropylene

Properties

Thermal Burning rate, mm · min⫺1 Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C

Copolymer

Polyallomer

Injection molding

40% glass-fiberreinforced

300– 380

5.5– 8.0 100– 600

3.5– 8.0 200– 700

8– 20

400– 500

16 1– 2

21 1

45– 50

170– 250

130– 200

130– 190

70– 110

550

1700

2– 2.3

6– 8 R80– R102

5– 7 R50– R96

R40– R90

R50– R85

14 R123

29 R123

No break 30– 40

21– 53 165– 225

53– 1068 100– 170

80– 900

91– 203

⬍27 480

75 1100

3.8– 4.4

4.5– 6

4– 5.5

3– 3.8

9.5

19.5

1.7– 2.5

4.5– 5.4

3.5– 4.3

2.5– 3.1

3– 3.4

128– 150

81– 100

68– 95

60– 90

83– 100

49

22

54– 60

48– 57

45– 57

90– 105 (66 lb · in⫺2 )

51– 56

135

249

160 0.44– 0.46

240 0.45– 0.50

140– 160 0.45– 0.50

0.12

0.15– 0.17

0.12– 0.17

0.09– 0.17

0.29

0.29

0.22

RIGHT

Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

Homopolymer

Impact copolymer

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Polybutylene extrusion

ROTATED

10.47

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Polyurethane

Silicone Epoxy molding and encapsulating compound

Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

Thermoset

Thermoset

1.1– 1.5 0.02– 1.5 12– 20

1.05 0.1– 0.2

120– 160 1.05– 1.25 0.7– 0.9 13– 25

Thermoset

Thermoset

Thermoset

0.99– 1.5

1.8– 1.94

1.84

22

8– 15

10

Crystal

85– 105 1.04– 1.05 0.03– 0.10 24 ⬎1016

1011 – 1015 4.0– 7.5

1011 – 1013 5.4– 7.6

1014 – 1015 2.7– 4.2 2.5

10– 100

4– 9

10.48

INTERACTIVE

Mechanical Compressive modulus, 10 3 lb · in⫺2

Unsaturated

ROTATED

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

Liquid

Polystyrene

LEFT

Cast resin, flexible

Mineraland/or glass-filled

Casting resin Thermoplastic elastomer

Styrenic

TABLE 10.2 Properties of Commercial Plastics (Continued) Polyurethane

Silicone

Casting resin Properties

Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

100– 700

20 100– 1000

3– 6

20 100– 1100

10– 100

610

10– 350

0.7– 4.5

19

0.7– 9 (A65– D80)

1334 to flexible 10– 100

21

0.175– 10

10– 11

10– 16

28

1000– 2500

(A15– A65)

No break

Crystal 11.5– 16 1– 2 380– 450

9– 14 M80– M90

17

8– 14 M60– M75

13– 427

16

13– 21

10– 350 1.5– 8.4

Polystyrene

350– 485 0.35– 1.0

4– 6.5

6– 8

5.3– 7.9

20– 50

30

70– 80

260

74– 100

0– 78 100– 200 Varies over wide range

100– 200

87– 93

300– 800

Varies over wide range

371 0.43

0.43

0.21

0.07– 0.31

0.15– 0.31

0.30

93 0.3 0.68

0.09– 0.13

RIGHT

Thermal Burning rate, mm · min⫺1 Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

Unsaturated

Cast resin, flexible

Epoxy molding and encapsulating compound

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1

Liquid

Thermoplastic elastomer

Mineraland/or glass-filled

Styrenic

ROTATED

10.49

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Styrenic Polystyrene

Acrylonitrile-butadiene-styrene copolymer Molding

Heatresistant

Extrusion

Heatresistant

Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

110– 125 1.05– 1.09 0.03– 0.12 20

88– 120 1.02– 1.06 0.20– 0.45 14– 20

110– 125 1.05– 1.08 0.20– 0.45 14– 20

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

100– 110 1.01– 1.04 0.20– 0.45 14– 20

Flameretarded

110– 125 1.16– 1.21 0.2– 0.6 14– 20

2.4– 5.0 2.4– 3.8 0.003– 0.008 0.007– 0.015

190– 440

140– 300

20% glassreinforced

100– 110 1.06– 1.07

1.22

16– 22

18

130– 310

10.50

INTERACTIVE

150– 390

Platable

ROTATED

Mechanical Compressive modulus, 10 3 lb · in⫺2

High-impact

LEFT

Properties

TABLE 10.2 Properties of Commercial Plastics (Continued) Styrenic Acrylonitrile-butadiene-styrene copolymer

Polystyrene

Molding

Properties

Thermal Burning rate, mm · min⫺1 Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2 ), ⬚C

Heatresistant

High-impact

Flameretarded

Platable

20% glassreinforced

11.5– 16 2– 60

5.2– 10 20– 100

7.2– 10 3– 20

4.5– 8 5– 70

6.5– 7.5 5– 25

340– 470

130– 420

300– 400

250– 350

300– 400

340– 390

710

8.9– 14 L80– L108

4– 14 R75– R115

10– 13 R100– R115

8– 11 R85– R105

9– 14 R100– R120

10.5– 11.5 R103– R109

15.5 M85

21– 181 320– 460

133– 640 130– 380

107– 347 300– 350

347– 400 230– 330

160– 640 320– 400

267– 283 330– 380

64 740

5– 7.8

2.5– 8.0

6– 7.5

4.8– 6.3

5– 8

6– 6.4

11

5.5– 7

4– 5.5

4– 6

1.3

14

1.3

60– 70

60– 130

60– 93

95– 110

65– 95

47– 53

21

93– 120

77– 104 annealed

104– 116 annealed

96– 102 annealed

90– 107 annealed

96– 102 annealed

99

110 0.3– 0.4 0.19– 0.34

RIGHT

Maximum recommended service temperature, ⬚C Specific heat, cal g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

Extrusion

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Heatresistant

ROTATED

10.51

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Styrenic

Sulfone

Styrene-acrylonitrile copolymer

Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

Unfilled

20% glass-fiberreinforced

115– 125 1.07– 1.08 0.2– 0.3

115– 125 1.22 0.15– 0.20

90– 110 1.03– 1.06 0.05– 0.10

200 1.24 0.22

200 1.46 0.23

230 1.37 0.43

16– 20

20

18

17

17

17

1015 3.14 3.26

3.7 3.7

0.004 0.008

0.002 0.009

Poly(ether sulfone)

Poly(phenyl sulfone)

220 1.29 1.1– 1.3 (saturated) 16

ROTATED

530

Unfilled

20% glass-fiberreinforced

LEFT

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz) Mechanical Compressive modulus, 10 3 lb · in⫺2

Polysulfone Styrenebutadiene copolymer, high-impact

370

INTERACTIVE

10.52

TABLE 10.2 Properties of Commercial Plastics (Continued) Styrenic

Sulfone

Styrene-acrylonitrile copolymer

Compressive strength, rupture of 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

14– 17 1– 4

19 1– 2

4– 9 13– 50

13.9 50– 100

22 2

30– 80

60

550

100– 1100

280– 450

390

1000

375

330

14– 17 M80– M90

20 R122

5.3– 9.4 M10– M68

15.4 M69, R120

23 M123

18.7 M88

12.4

19– 27 400– 560

53 1150– 1200

32– 192 280– 465

64 360

59 1200

85 350

640 310

9– 12

15.8– 18

3.2– 4.9

12.2

10.4

Unfilled

Unfilled

20% glass-fiberreinforced

Poly(ether sulfone)

Poly(phenyl sulfone)

17

2.9– 4.9

10.2

36– 38

38– 40

70– 101

52– 56

25

55

31

88– 104

99

74– 93

174

182

203

204

0.38

0.14– 0.19

149

0.12

0.26– 0.28

0.12– 0.21

0.12

RIGHT

Thermal Burning rate, mm · min⫺1 Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

20% glass-fiberreinforced

DEAN 37261 (McGHP)

Properties

Polysulfone Styrenebutadiene copolymer, high-impact

ROTATED

10.53

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Thermoplastic elastomers

Properties Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm⫺1

Polyolefin

Polyester

Block copolymers of styrene and butadiene or styrene and isoprene

Block copolymers of styrene and ethylene or styrene and butylene

168– 206 0.88– 0.90 0.01 24– 26

1.17– 1.25

Urea formaldehyde, alpha-cellulose filled

Poly(vinyl chloride) and poly(vinyl acetate)

Rigid

Flexible and unfilled

Thermoset 0.9– 1.2 0.19– 0.39 16– 21

0.9– 1.2

75– 105 1.30– 1.58 0.04– 0.4 14– 20

75– 105 1.16– 1.35 0.15– 0.75 12– 16

0.5– 5.0 7.7– 9.5 6.7– 8.0

1012 – 1015 3.2– 4.0 3.0– 4.0

1011 – 1014 5.0– 9.0 3.0– 4.0

0.036– 0.043 0.025– 0.035

0.01– 0.02 0.006– 0.02

0.03– 0.05 0.06– 0.1

ROTATED

1.47– 1.52 0.4– 0.8 12– 16

LEFT

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz) Mechanical Compressive modulus, 10 3 lb · in⫺2

Vinyl

3.6– 120

INTERACTIVE

10.54

TABLE 10.2 Properties of Commercial Plastics (Continued) Thermoplastic elastomers

Properties

Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Polyester

Block copolymers of styrene and butadiene or styrene and isoprene

Block copolymers of styrene and ethylene or styrene and butylene

Urea formaldehyde, alpha-cellulose filled

Rigid

Flexible and unfilled

150– 300

350– 450

500– 1350

600– 800

25– 45 ⬍1

8– 13 40– 80

1.5– 2.0

7– 75

4– 150

4– 100

1300– 1600

300– 500

(A65– A92)

(D40– D72)

(A40– A90)

(A50– A90)

10– 18 M110– M120

10– 16 (D65– D95)

No break

208 to no break

No break

No break

13– 21

21– 1068

1.1– 2.5

0.8– 50

1000– 1500

350– 600

3.7– 5.7

0.6– 3.0

5.5– 13

6– 75

1.5– 3.5

Selfextinguishing

Slow to selfextinguishing 70– 250

0.65– 2.0

Thermal Burning rate, mm · min⫺1

1– 3

Selfextinguishing 130– 170

0.19– 0.21

0.9– 1.7 200– 450

(A50– A100) Varies over wide range

130– 137

22– 36

50– 100

⬍0– 49

127– 143

60– 77

77 0.6

70– 74 0.2– 0.28

80– 105 0.36– 0.5

0.30– 0.42

0.15– 0.21

0.13– 0.17

0.15

RIGHT

Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

Poly(vinyl chloride) and poly(vinyl acetate)

DEAN 37261 (McGHP)

Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1

Polyolefin

Vinyl

ROTATED

10.55

INTERACTIVE

DEAN 37261 (McGHP)

TABLE 10.2 Properties of Commercial Plastics (Continued) Vinyl Poly(vinyl chloride) and poly(vinyl acetate)

Properties

Chlorinated poly(vinyl chloride)

Poly(vinyl butyral), flexible

210 1.65– 1.72 0.1 16– 24

105 1.2– 1.4 0.5– 3.0 19

110 1.49– 1.56 0.02– 0.15

1014 – 1016 4.5– 6.0

49 1.05 1.0– 2.0 14

335– 600

10.56

INTERACTIVE

Mechanical Compressive modulus, 10 3 lb · in⫺2

75– 105 1.54 0.01 24– 31

Poly(vinyl formal)

ROTATED

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (10 6 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (10 6 Hz)

75– 105 1.3– 1.7 0.5– 1.0 9.8– 12

Poly(vinylidene chloride)

LEFT

Physical Melting temperature, ⬚C Crystalline Amorphous Specific gravity Water absorption (24 h),% Dielectric strength, kV · mm⫺1

Flexible and filled

Poly(vinyl chloride), 15% glass-fiberreinforced

TABLE 10.2 Properties of Commercial Plastics (Continued) Vinyl Poly(vinyl chloride) and poly(vinyl acetate)

Poly(vinylidene chloride)

Poly(vinyl formal)

Chlorinated poly(vinyl chloride)

1.0– 1.8 200– 400

9 2– 3

2– 2.7 50– 250

5– 20

9– 22 4– 65

750

(A50– A100) Varies over wide range

1– 3.5

4.2– 6.2 M50– M65

17– 18 M85

14.5– 17 R117– R122

53 870

16– 53 50– 80

43– 75 350– 600

53– 299 360– 475

9.5

3– 5

10– 12

7.5– 9

Selfextinguishing

68

190

64

68– 78

54– 71

71– 77

94– 112

0.16

0.14

0.13

0.5– 3.0

Slow

100 0.32 0.13– 0.17

A10– A100 Varies over wide range

RIGHT

Coefficient of linear thermal expansion, 10⫺6 ⬚C Deflection temperature under flexural load (264 lb · in⫺2), ⬚C Maximum recommended service temperature, ⬚C Specific heat, cal · g⫺1 Thermal conductivity, W · m⫺1 · K ⫺1

150– 450

380– 450

13.5 R118

Thermal Burning rate, mm · min⫺1

Poly(vinyl butyral), flexible

DEAN 37261 (McGHP)

Properties Compressive strength, rupture or 1% yield, 10 3 lb · in⫺2 Elongation at break, % Flexural modulus at 23⬚C, 10 3 lb · in⫺2 Flexural strength, rupture or yield, 10 3 lb · in⫺2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23⬚C, J · m⫺1 Tensile modulus, 10 3 lb · in⫺2 Tensile strength at break, 10 3 lb · in⫺2 Tensile yield strength, 10 3 lb · in⫺2

Flexible and filled

Poly(vinyl chloride), 15% glass-fiberreinforced

ROTATED

10.57

INTERACTIVE

DEAN #37261

10.58

10.4 10.4.1

LEFT

(McGHP)

INTERACTIVE

SECTION 10

FORMULAS AND ADVANTAGES OF RUBBERS

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Gutta Percha

Gutta percha is a natural polymer of isoprene (3-methyl-1,3-butadiene) in which the configuration around each double bond is trans. It is hard and horny and has the following formula:

10.4.2

Natural Rubber

Natural rubber is a polymer of isoprene in which the configuration around each double bond is cis (or Z):

Its principal advantages are high resilience and good abrasion resistance.

10.4.3

Chlorosulfonated Polyethylene

Chlorosulfonated polyethylene is prepared as follows:

Cross-linking, which can occur as a result of side reactions, causes an appreciable gel content in the final product. The polymer can be vulcanized to give a rubber with very good chemical (solvent) resistance, excellent resistance to aging and weathering, and good color retention in sunlight.

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DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

10.4.4

10.59

Epichlorohydrin

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Epichlorohydrin is a product of covulcanization of epichlorohydrin (epoxy) polymers with rubbers, especially cis-polybutadiene. Its advantages include impermeability to air, excellent adhesion to metal, and good resistance to oils, weathering, and low temperature.

10.4.5

Nitrile Rubber (NBR, GRN, Buna N)

Nitrile rubber can be prepared as follows:

Nitrile rubber is also known as nitrile-butadiene rubber (NBR), government rubber nitrile (GRN), and Buna N. It possesses resistance to oils up to 120⬚C and excellent abrasion resistance and adhesion to metal.

10.4.6

Polyacrylate

Polyacrylate has the following formula:

It possesses oil and heat resistance to 175⬚C and excellent resistance to ozone.

10.4.7 cis-Polybutadiene Rubber (BR) cis-Polybutadiene is prepared by polymerization of butadiene by mostly 1,4-addition. CH2 " CH9CH"CH2 : [ 9CH2 9CH"CH9CH2 9]n The polybutadiene produced is in the Z (or cis) configuration. cis-Polybutadiene has good abrasion resistance, is useful at low temperature, and has excellent adhesion to metal.

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DEAN #37261

10.60

10.4.8

LEFT

(McGHP)

INTERACTIVE

SECTION 10

Polychloroprene (Neoprene)

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Polychloroprene is prepared as follows:

It has very good weathering characteristics, is resistant to ozne and to oil, and is heat-resistant to 100⬚C.

10.4.9

Ethylene-Propylene-Diene Rubber (EPDM)

Ethylene-propylene-diene rubber is polymerized from 60 parts ethylene, 40 parts propylene, and a small amount of nonconjugated diene. The nonconjugated diene permits sulfur vulcanization of the polymer instead of using peroxide. It is a very lightweight rubber and has very good weathering and electrical properties, excellent adhesion, and excellent ozone resistance.

10.4.10

Polyisobutylene (Butyl Rubber)

Polyisobutylene is prepared as follows:

It possesses excellent ozone resistance, very good weathering and electrical properties, and good heat resistance.

10.4.11

(Z)-Polyisoprene (Synthetic Natural Rubber)

Polymerization of isoprene by 1,4-addition produces polyisoprene that has a cis (or Z) configuration.

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DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

10.4.12

10.61

Polysulfide Rubbers

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Polysulfide rubbers are prepared as follows: Cl9 R9 Cl ⫹ Na 9 S9S9S9S9Na : HS[ 9R9S9S9S9 S9 ]n R9 SH where R can be 9 CH2CH2 9 , 9CH2CH2 9O 9 CH2CH2 9, or

9CH2CH2 9O 9CH2 9O9CH2CH2 9 .

Polysulfide rubbers possess excellent resistance to weathering and oils and have very good electrical properties.

10.4.13

Poly(vinyl Chloride) (PVC)

Poly(vinyl chloride) as previously discussed in Sec. 10.3, Formulas and Key Properties of Plastic Materials, has the following structures:

PVC polymer plus special plasticizers are used to produce flexible tubing which has good chemical resistance.

10.4.14

Silicone Rubbers

Silicone rubbers are prepared as follows:

Other groups may replace the methyl groups. Silicone rubbers have excellent ozone and weathering resistance, good electrical properties, and good adhesion to metal.

10.4.15

Styrene-Butadiene Rubber (GRS, SBR, Buna S)

Styrene-butadiene rubber is prepared from the free-radical copolymerization of one part by weight of styrene and three parts by weight of 1,3-butadiene. The butadiene is incorporated by both 1,4addition (80%) and 1,2-addition (20%). The configuration around the double bond of the 1,4-adduct is about 80% trans. The product is a random copolymer with these general features:

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DEAN #37261

LEFT

(McGHP)

10.62

INTERACTIVE

SECTION 10

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Styrene-butadiene rubber (SBR) is also known as government rubber styrene (GRS) and Buna S.

10.4.16

Urethane

See Table 10.3.

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DEAN #37261

TABLE 10.3 Properties of Natural and Synthetic Rubbers

Tensile strength, lb · in⫺2 (23⬚C)

Minimum

Maximum

1.2– 1.95 0.93 1.10 1.27 1.4– 1.95

(65– 95) 20– 100 50– 95 60– 90 60– 90

3– 8 750– 850 100– 500 100– 400 100– 350

4000– 10,000 3000– 4500 500– 3000 1000– 2500 2000– 3000

⫺56 ⫺54 ⫺46 ⫺40

104 82 121 121 232

0.91

(40– 70)

750– 950

2300– 3000

1.00 1.10 0.93 1.23 0.85 0.92 0.94 1.34 1.32

30– 100 40– 100 30– 100 20– 90 30– 100 30– 100 20– 100 20– 80 (80– 90)

100– 600 100– 400 100– 700 800– 1000 100– 300 100– 700 100– 750 100– 400

0.98 0.94 0.85

20– 95 40– 100 62– 95

50– 800 400– 600 100– 700

500– 4000 1000– 2200 2500– 3000 2000– 3500 1000– 3000 1000– 3000 2000– 3000 700– 1250 2400– 3000 700– 800 500– 1500 1600– 3700 1000– 8000

121 ⫺54 ⫺18 ⫺62 ⫺54 ⫺40 ⫺54 ⫺54 ⫺54

INTERACTIVE

⫺84 ⫺60 ⫺54

121 149 79– 100 121 149 100 79– 82 82– 100 71 316 232 107 100

RIGHT

Gutta percha (hard rubber) Natural rubber (NR) Chlorosulfonated polyethylene Epichlorohydrin Fluoroelastomers Isobutene-isoprene rubber (IIR) [also known as government rubber I(GR-I)] Nitrile rubber (butadiene-acrylonitrile rubber) (also known as Buna N and NBR) Polyacrylate Polybutadiene rubber (BR) Polychloroprene (neoprene) Poly(ethylene-propylene-diene) (EPDM) Polyisobutylene (butyl rubber) Polyisoprene Polysulfide (Thiokol ST) Poly(vinyl chloride) (Koroseal) Silicone, high-temperature Silicone Styrene-butadiene rubber (SBR) (also known as Buna S) Urethane

Specific gravity

Ultimate elongation % (23⬚C)

(McGHP)

Rubber

Service temperature, ⬚C

Durometer hardness (or Shore)

10.63

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DEAN #37261

10.5

CHEMICAL RESISTANCE

TABLE 10.4 Resistance of Selected Polymers and Rubbers to Various Chemicals at 20⬚C

(McGHP)

The information in this table is intended to be used only as a general guide. The chemical resistance classifications are E ⫽ excellent (30 days of exposure causes no damage), G ⫽ good (some damage after 30 days), F ⫽ fair (exposure may cause crazing, softening, swelling, or loss of strength), N ⫽ not recommended (immediate damage may occur).

Esters

Ethers

Glycols

Hydrocarbons, aliphatic

Hydrocarbons, aromatic

Hydrocarbons, halogenated

Ketones

Oxidizing agents, strong

N — — N

N N N N

N N — N

N E — N

G E — G

N G E F

N N G N

N N G N

N N N N

N N — —

E N G G E E E G

E N N G E E E F

E G G N G E E E

E E F — G G E —

E E N N E E E —

E G N N G G G —

E — N F N N N —

E G G G E E E —

E G N G F F G —

E F N F G F G E

E F N F N N N E

E G N N F G G E

E N N F F F F —

Aldehydes

F E — N

Alcohols, aliphatic

N N — N

Acids, strong and concentrated

F G G F

Acids, dilute or weak

Alkalies, concentrated

Chemical

Polymers

LEFT

10.64

INTERACTIVE

Acetals Acrylics: poly(methyl methacrylate) Allyls: diallyl phthalate Cellulosics: cellulose-acetate-butyrate and celluloseacetate-propionate polymers Fluorocarbons Polyamides Polycarbonates Polyesters Poly(methyl pentene) Low-density polyethylene High-density polyethylene Polybutadiene

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DEAN #37261

Hydrocarbons, halogenated

Oxidizing agents, strong

Hydrocarbons, aromatic

G N N F F G

F N — N N N

N N — N N N

G N — N N N

F N — — G G

— — — — — —

N N N F E N

N G F F E N

E E E E E E

N E F N E N

N N N N F N

N N N N N N

N N N N N N

— — — — — —

Ketones

Hydrocarbons, aliphatic

E E F — G F

Glycols

N — — — F F

Ethers

G N — N N N

Esters

E N N G E G

Alkalies, concentrated

Aldehydes

Alcohols, aliphatic

Acids, strong and concentrated

Acids, dilute or weak

(McGHP)

Chemical

Polymers Polypropylene and polyallomer Polystyrene Styrene-acrylonitrile copolymers Styrene-acrylonitrile-butadiene copolymers Sulfones: polysulfone Vinyls: poly(vinyl chloride)

E N — — G E

E N — N N G

E E N G F E

E — — — F G

RIGHT

Rubbers — — — — — —

— — — — — —

E E E E E E

— — — — — —

10.65

INTERACTIVE

Natural rubber Nitrile rubber Polychloroprene Polyisobutylene Polysulfide rubbers: Thiokol Styrene-butadiene rubber

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10.6

GAS PERMEABILITY

TABLE 10.5 Gas Permeability Constants (1010 P) at 25⬚C for Polymers and Rubbers The gas permeability constant P is defined as

(McGHP)

P⫽

amount of permeant (area) ⫻ (time) ⫻ (driving forced across the film)

The gas permeability constant is the amount of gas expressed in cubic centimeters passed in 1 s through a 1-cm2 area of film when the pressure across a film thickness of 1 cm is 1 cmHg and the temperature is 25⬚C. All tabulated values are multiplied by 1010 and are in units of seconds⫺1 (centimeters of Hg)⫺1. Other temperatures are indicated by exponents and are expressed in degrees Celsius. Gas Polymer or rubber Cellulose (cellophane) Cellulose acetate Cellulose nitrate Ethyl cellulose

He

N2

0.00520 13.620

0.003 2 0.2830

6.9 40030

0.5320

Nylon 11

1.9530

Poly(acrylonitrile)

0.002 1 0.7830

CO2 0.004 7 22.730

0.12 8.430

2.020 8720

1.95 26.530

2.12 41.030

2.17 9.43

14.4 52.0

6.16 23.3

35.4 15.3

0.009 530

0.03830 1.7830

0.1030

H2O 1 900 5 500 6 290 12 00020 510 2 290

177

1.0040 0.000 2

0.000 8

Other 0.00645 (H2S); 0.001 7 (SO2 ) 3.530 (H2S); 170 (ethylene oxide); 6.860 (bromomethane) 57.1 (NH3 ); 1.76 (SO2 ) 705 (NH3 ); 204 (SO2 ); 4200 (ethylene oxide) 15.7 (CO); 30.1 (CH4 ); 1.68 (C3H8 ); 98.9 (C2H2 ); 550 (CH3C # CH); 3.59 (SF6 ) 0.3330 (H2S); 1.220 (NH3 ); 0.8460 (CH3Br) 0.34430 (Ne); 0.18940 (Ar); 13.650 (propyne)

INTERACTIVE

Nylon 6

0.006 5 3.520

O2

LEFT

Gutta percha Natural rubber

H2

300

10.66

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DEAN #37261

TABLE 10.5 Gas Permeability Constants (1010 P) at 25⬚C for Polymers and Rubbers (Continued)

Polymer or rubber Acrylonitrile-styrene copolymer (66 : 34) Poly(1,3-butadiene) Poly (cis-1,4-butadiene) Butadiene-acrylonitrile copolymer (80 : 20) Butadiene-styrene copolymer (80 : 20) Butadiene-styrene copolymer (92 : 8) Polychloroprene Polyethylene, low-density

He

N2

H2

41.9

32.6

6.42 19.2

0.048 19.0

CO2

H2O

0.21 138.0

2 000 5 070

Other

19.2 (Ne); 41.0 (Ar) 30.8

13.6 12.030

4.0 2.88

25.8 12.6

Polyethylene, high-density

1.14

0.143

3.020

0.403

0.36

Poly(ethylene terephthalate) Crystalline Amorphous Poly(ethyl methacrylate)

1.32 3.28 6.82

0.006 5 0.013 0.220

3.7020

0.035 0.059 1.15

0.17 0.30 5.00

8.38

0.324

7.20

1.30

5.16

7.77

0.181

7.41

0.852

4.32

90

12.0

130 3 200

11038

24.8 (C2H2 ); 7.7 (propyne) 5.01 (Ne); 4.49 (Ar) 9.70 (Ne); 12.7 (Ar) 3.79 (Ar); 3.27 (CH4 ) 2.88 (CH4 ); 6.81 (C2H6 ); 9.43 (C3H8 ); 1.48 CO); 490 (ethylene oxide); 14.4 (propene); 42.2 (propyne); 0.170 (SF6 ); 47260 (CH3Br) 0.388 (CH4 ); 0.590 (C2H6 ); 0.537 (C3H8 ); 0.008 3 (SF6 ); 1.69 (Ar); 4.01 (propene) 0.003 2 (CH4 ); 0.0860 (CH3Br) 0.009 (CH4 ) 2.98 (Ne); 0.565 (Ar); 0.370 (Kr); 3.83 (H2S); 0.000 001 65 (SF6 )

INTERACTIVE

3.85

RIGHT

15.9

4.9

1.06 1.71 5.11 1.2 0.969

Isobutene-isoprene copolymer (98 : 2) Isoprene-acrylonitrile copolymer (76 : 24)

12.2 13.4 22.9

O2

(McGHP)

Gas

13.650 (C3H8 )

10.67

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DEAN #37261

TABLE 10.5 Gas Permeability Constants (1010 P) at 25⬚C for Polymers and Rubbers (Continued) Gas Polymer or rubber

H2

O2

0.596

13.6

2.34

14.1

101 3820 2330

7.83 0.4430 2270

136 4120 4640

0.004 8 32.0 2.330 4890

0.014 92.6 9.230 3 240

Polystyrene Poly(tetrafluoroethylene) Poly(trifluoroethylene)

18.7

0.788 1.4 0.003

Poly(vinyl acetate)

12.630

6.820

⬍0.00114

0.00130

Poly(vinyl chloride)

2.05

0.011 8

Poly(vinylidene chloride)

0.3134

0.000 9430

2.63 4.2 0.02540

8930

0.5030

10.5 11.7 0.04840

0.009

0.008 9

0.00123

1.70

0.045 3

0.157

0.005 330

0.0330

H2O

Other

600 51 43 00035

0.3320 (H2S); 9.220 (NH3 ) 1910 (Ne); 5500 (Ar); 1 0200 (Kr); 2 5500 (Xe); 19 0000 (butane)

1 200 0.29

275 0.5

15.7 (NO2 ); 37.5 (N2O4 ) 1.20 (ethylene oxide); 4.660 (CH3Br) 2.6430 (Ne); 0.1930 (Ar); 0.07830 (Kr); 0.05030 (CH4 ) 0.007 (H2S); 0.0020 (ethylene oxide) 3.92 (Ne); 0.011 5 (Ar); 0.028 6 (CH4 ) 0.0330 (H2S); 0.00860 (CH3Br)

LEFT

Poly(vinyl alcohol)

23.3 9.8 0.9420

CO2

(McGHP)

N2

Isoprene-methacrylonitrile copolymer (76 : 24) Methacrylonitrile-styrenebutadiene copolymer (88 : 7 : 5) Poly(methylpentene) Polypropylene Silicone rubber, 10% filler

He

INTERACTIVE

10.68

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DEAN #37261

TABLE 10.6 Vapor Permeability Constants (1010 P) at 35⬚C for Polymers All tabulated values are multiplied by 1010 and are in units of seconds⫺1 (centimeters of Hg)⫺1.

Polymer

Benzene

Hexane

Cellulose Cellulose acetate Poly(acrylonitrile) Polyethylene, low-density Polystyrene Poly(vinyl alcohol)

1.4 512 2.61 5 300 10 600 3.58

0.912 2.80 1.59 2 910

10.7

2.34

Carbon tetrachloride

Ethanol

Ethyl acetate

0.836 3.74 1.47 3 810 6 820 1.61

85.8 2 980 0 55.9 0 32.7

13.4 3 595 1.34 513 soluble 2.53

(McGHP)

Vapor

FATS, OILS, AND WAXES RIGHT

TABLE 10.7 Constants of Fats and Oils Specific gravity (15⬚C/15⬚C)

Refractive index

Acid value

Saponification value

Iodine value

0.5– 35 1.2 5.6 0.8– 5.3

210– 230 193– 205 171– 189 195– 200

26– 38 66– 72 137– 166 26– 36

INTERACTIVE

Fat or oil

Solidification point, ⬚C

Animal origin Butterfat Chicken fat Cod-liver oil Deer fat

20– 23 21– 27 ⫺3

⬚C 0.9140 15⬚C 0.924 0.92– 0.93 0.96– 0.97

1.4540⬚C 1.48125⬚C

10.69

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Fat or oil

Solidification point, ⬚C

Specific gravity (15⬚C/15⬚C)

Refractive index

Acid value

Saponification value

2– 12

203 (body); 290 (jaw) 233– 236 191– 193 170– 194 195– 200 193– 200 193– 198 195– 203 189– 193 193– 199 203 199– 203 188– 196 188– 196 157– 164 120– 137 196– 200 195– 196 160– 202

DEAN #37261

TABLE 10.7 Constants of Fats and Oils (Continued)

Iodine value

Animal origin (continued)

22– 24 20– 45 15 ⫺2 to ⫹4 27– 30 ⫺5 ⫺2 to ⫹10 ⫺16 17– 23 20– 22 3 15.5 31– 38 32– 41 ⫺2 to 0

0.91– 0.93 ⬚C 0.91– 0.9438 38⬚C 0.92– 0.93 0.92– 0.94 0.92– 0.93 0.903 0.913– 0.915 0.93– 0.94 0.92– 0.93 0.91– 0.92 0.926 0.93– 0.94 0.92– 0.93 0.915– 0.926 0.916– 0.919 0.878– 0.884 0.895 0.937– 0.953 0.917– 0.924

1.461060⬚C 1.460 1.462 1.462 1.46560⬚C 1.46425⬚C

1.46660⬚C

1.45740⬚C 1.46060⬚C

0.6 1.8– 44 0– 2.4 0.1– 2.5 0.5– 0.8 3– 12 0.1– 0.6 1.2 1.4– 7.2 4– 25 1.9– 40 13 0.25 2– 14 1.9

127 (body); 33 (jaw) 25– 37 58– 67 102– 149 75– 86 57– 73 63– 79 47– 67 148– 185 58– 75 127 70– 100 130– 152 130– 152 115– 139 80– 84 35– 42 48– 61 90– 146

LEFT

Goat butter Goose fat Herring oil Horse fat Human fat Lard oil Lard oil, fatty tissue Menhaden oil Neat’s-foot oil Porpoise, body oil Rabbit fat Sardine oil Seal Shark Sperm oil Tallow, beef Tallow, mutton Whale oil

⫺3 to ⫹5

(McGHP)

Dolphin

Plant origin ⫺10 ⫺20 to ⫺15 22– 26 ⫺17

0.916 0.914– 0.921 0.89360⬚C 0.922

0.5– 3.5 1.44360⬚C

199 183– 208 247 191– 196

100 93– 103 16 97– 111

10.70

INTERACTIVE

Acorn Almond Babassu oil Beechnut oil

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Fat or oil

Solidification point, ⬚C

Specific gravity (15⬚C/15⬚C)

Refractive index

Acid value

Saponification value

Iodine value

1.477

0.1– 0.8

1.45740⬚C 1.44940⬚C 1.47340⬚C 1.47440⬚C

2.4 1.1– 1.9 2.5– 10 1.4– 2.0 0.6– 0.9

175– 183 196– 213 179– 206 193– 195 153– 262 187– 193 194– 196 191– 197 190– 195 188– 195 173– 175 195 190

84 98– 110 23– 41 33– 42 6– 10 111– 128 103– 111 87 145– 162 175– 202 99– 110 71 129 140– 180 79– 88 49– 59 26– 32 88– 98 185– 206 83– 87 128– 141 121– 130 94– 105 122– 141 103– 117 122– 134 129– 136 163– 171 94– 98 125

DEAN #37261

TABLE 10.7 Constants of Fats and Oils (Continued)

Plant origin (continued) ⫺18 to ⫺17 ⬍⫺25 24– 34 21.5– 23 14– 22 ⫺20 to ⫺10 ⫺13 to ⫹12 ⫺18 to ⫺17 ⫺28 to ⫺15 ⫺27 to ⫺19 16 ⫺3

0.45 1– 3.5 5.7– 7.3

1.46840⬚C 1.45840⬚C 1.45740⬚C 1.46940⬚C 1.48125⬚C

0.3– 1.0 10 0.3– 0.6 0.8

1.46940⬚C

2.5

1.47140⬚C 1.46260⬚C 1.46540⬚C 1.47340⬚C 1.46940⬚C 1.51725⬚C

0.36– 1.0 0.6 9.8 0.3– 1.8 11.2 2 5.4

185– 196 200– 205 220– 231 186– 194 188– 194 191 193– 195 188– 193 168– 179 188– 203 188– 193 189– 194 188– 193 190– 197 171– 174

INTERACTIVE

⫺10 to ⫺5 ⫺18 to ⫺16 ⫺15 ⫺10 ⫺18 to ⫺13 ⫺6 to ⫺4 ⫺16 to ⫺10 ⫺17 ⫺2.5 ⫺16 to ⫺8

1.47825⬚C 1.47540⬚C 1.46240⬚C 1.47140⬚C

RIGHT

⫺6 35– 42 24 3

0.960– 0.967 0.95025⬚C 0.918– 0.922 0.964– 0.974 0.926 0.921– 0.928 ⬚C 0.91825 25⬚C 0.917 0.928– 0.934 0.930– 0.938 0.918– 0.921 0.917 0.925 0.97425⬚C 0.914– 0.918 0.915 0.918– 0.925 0.917– 0.926 0.930– 0.937 0.913– 0.919 0.924– 0.926 0.923– 0.925 0.913– 0.917 0.925– 0.928 ⬚C 0.91925 25⬚C 0.924– 0.927 0.924– 0.926 0.94– 0.95 0.912– 0.916

(McGHP)

Castor oil Chaulmoogra oil, USP Chinese vegetable tallow Cocoa butter Coconut oil Corn (maize) oil Cottonseed oil Hazelnut oil Hemp-seed oil Linseed oil Mustard, black, oil Neem oil Niger-seed oil Oiticica oil Olive oil Palm oil Palm kernel oil Peanut oil Perilla oil Pistachio-nut oil Poppy-seed oil Pumpkin-seed oil Rapeseed oil Safflower oil Sesame oil Soybean oil Sunflower-seed oil Tung oil White-mustard-seed oil Wheat-germ oil 10.71

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TABLE 10.8 Constants of Waxes

Bamboo leaf Bayberry (myrtle) Beeswax, ordinary Beeswax, East Indian Beeswax, white, USP Candelilla Cape berry Caranda Carnauba, No. 1 yellow Carnauba, No. 3, crude Carnauba, No. 3, refined Castor oil, hydrogenated Chinese insect Cotton Cranberry Esparto Flax Japan Jojoba

79– 80 47– 49 62– 66 61– 67 61– 69 73– 77 40– 45 80– 85 86– 88 86– 90 86– 89 83– 88 80– 85 68– 71 207– 218 75– 79 61– 70 49– 56 11– 12

0.96125⬚C 0.99 0.95– 0.97 0.95– 0.97 0.95– 0.98 0.98– 0.99 1.01 0.99– 1.00 0.99– 1.00 0.99– 1.01 0.96– 0.97 0.98– 0.9920⬚C 0.95– 0.97 0.96 0.97– 0.98 0.985– 0.995 0.91– 0– 0.99 0.97– 1.00 0.86– 0.9025⬚C

Refractive index 1.43680⬚C 1.44– 1.4840⬚C 1.4440⬚C 1.45– 1.4765⬚C 1.45– 1.4685⬚C 1.4545⬚C

1.4740⬚C 1.4640⬚C

1.46525⬚C

Acid value

Saponification value

Iodine value

14– 15 3– 4 17– 21 5– 10.5 17– 24 19– 24 2.5– 4.0 5.0– 9.5 1.5– 2.5 3.0– 8.5 3.0– 5.0 1.0– 5.0 2– 9 32 42– 59 22– 27 17– 48 4– 15 0.2– 0.6

43– 44 205– 212 88– 100 87– 117 90– 96 55– 64 211– 215 64– 79 75– 86 75– 89 76– 85 177– 181 78– 93 71 131– 134 58– 73 37– 102 210– 235 92– 95

7.8 4– 9.5 8– 11 4– 10.5 7– 11 14– 20 0.5– 2.5 8– 9

7– 13.5 2.5– 8.5 1.0– 2.5 25 44– 53 7– 15 22– 29 4– 15 82– 88

LEFT

Specific gravity (15⬚C/15⬚C)

(McGHP)

Wax

Melting point, ⬚C

INTERACTIVE

10.72

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TABLE 10.8 Constants of Waxes (Continued) Specific gravity (15⬚C/15⬚C)

Microcrystalline, amber Microcrystalline, white Montan, crude Montan, refined Ouricury Ozokerite Palm Paraffin, American Shellac Sisal hemp Spermaceti Sugarcane, refined Wool

64– 91 71– 89 76– 86 77– 84 86– 89 56– 82 74– 86 49– 63 79– 82 74– 81 41– 49 76– 82 38– 40

0.91– 0.94 0.93– 0.94 1.01– 1.0225⬚C 1.02– 1.04 0.99– 1.01 0.90– 1.00 0.99– 1.05 0.896– 0.925 0.97– 0.98 1.007– 1.010 0.905– 0.960 0.96– 0.98 0.97

Refractive index

Acid value

Saponification value

1.42– 1.45 80⬚C 1.44180⬚C

0 0 22– 31 23– 45 12– 19 0 5– 11 0 12– 24 16– 19 0.5– 3.0 8– 23 6– 22

0 0 59– 92 72– 115 88– 96 0 64– 104 0 64– 83 56– 58 121– 135 55– 70 82– 130

1.44– 1.4880⬚C

1.5125⬚C 1.4840⬚C

Iodine value 0 0 14– 18 10– 14 6.9– 7.8 4– 8 9– 17 0 6– 9 28– 29 2.5– 8.5 13– 29 15– 47

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Wax

Melting point, ⬚C

INTERACTIVE

10.73

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SECTION 11

PRACTICAL LABORATORY INFORMATION 11.1

COOLING Table 11.1 Cooling Mixtures Table 11.2 Molecular Lowering of the Melting or Freezing Point 11.2 DRYING AND HUMIDIFICATION Table 11.3 Drying Agents Table 11.4 Solutions for Maintaining Constant Humidity Table 11.5 Concentration of Solutions of H2SO4, NaOH, and CaCl2 Giving Specified Vapor Pressures and Percent Humidities at 25ⴗC Table 11.6 Relative Humidity from Wet and Dry Bulb Thermometer Readings Table 11.7 Relative Humidity from Dew Point Readings 11.3 BOILING POINTS AND HEATING BATHS Table 11.8 Organic Solvents Arranged by Boiling Points Table 11.9 Molecular Elevation of the Boiling Point Table 11.10 Substances Which Can Be Used for Heating Baths 11.4 SEPARATION METHODS Table 11.11 Solvents of Chromatographic Interest Table 11.12 Solvents Having the Same Refractive Index and the Same Density at 25ⴗC Table 11.13 McReynolds’ Constants for Stationary Phases in Gas Chromatography 11.4.1 McReynolds’ Constants Table 11.14 Characteristics of Selected Supercritical Fluids 11.4.2 Chromatographic Behavior of Solutes Table 11.15 Typical Performances in HPLC for Various Conditions 11.4.3 Ion-Exchange (Normal Pressure, Columnar) Table 11.16 Guide to Ion-Exchange Resins Table 11.17 Relative Selectivity of Various Counter Cations Table 11.18 Relative Selectivity of Various Counter Anions 11.5 GRAVIMETRIC ANALYSIS Table 11.19 Gravimetric Factors Table 11.20 Elements Precipitated by General Analytical Reagents Table 11.21 Cleaning Solutions for Fritted Glassware Table 11.22 Common Fluxes Table 11.23 Membrane Filters Table 11.24 Porosities of Fritted Glassware Table 11.25 Tolerances for Analytical Weights Table 11.26 Heating Temperatures, Composition of Weighing Forms, and Gravimetric Factors 11.6 VOLUMETRIC ANALYSIS 11.6.1 Acid-Base Titrations in Aqueous Media Table 11.27 Primary Standards for Aqueous Acid-Base Titrations Table 11.28 Titrimetric (Volumetric) Factors 11.6.2 Titrimetric (Volumetric) Factors for Acid-Base Titrations 11.6.3 Standard Volumetric (Titrimetric) Redox Solutions 11.6.4 Indicators for Redox Titrations Table 11.29 Equations for the Redox Determinations of the Elements with Equivalent Weights 11.1

11.3 11.3 11.4 11.5 11.5 11.6 11.7 11.8 11.9 11.10 11.10 11.13 11.15 11.16 11.16 11.18 11.21 11.26 11.26 11.27 11.31 11.32 11.33 11.37 11.38 11.41 11.41 11.67 11.69 11.70 11.70 11.71 11.71 11.72 11.74 11.74 11.74 11.76 11.82 11.82 11.83 11.84

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SECTION 11

11.6.5 Precipitation Titrations 11.6.6 Complexometric Titrations 11.6.7 Masking Agents 11.6.8 Demasking Table 11.30 Standard Solutions for Precipitation Titrations Table 11.31 Indicators for Precipitation Titrations Table 11.32 Properties and Applications of Selected Metal Ion Indicators Table 11.33 Variation of ␣4 with pH Table 11.34 Formation Constants of EDTA Complexes at 25ⴗC, Ionic Strength Approaching Zero Table 11.35 Cumulative Formation Constants of Ammine Complexes at 20ⴗC, Ionic Strength 0.1 Table 11.36 Masking Agents for Various Elements Table 11.37 Masking Agents for Anions and Neutral Molecules Table 11.38 Common Demasking Agents Table 11.39 Amino Acids pI and pKa Values Table 11.40 Tolerances of Volumetric Flasks Table 11.41 Pipet Capacity Tolerances Table 11.42 Tolerances of Micropipets (Eppendorf) Table 11.43 Buret Accuracy Tolerances Table 11.44 Factors for Simplified Computation of Volume Table 11.45 Cubical Coefficients of Thermal Expansion Table 11.46 General Solubility Rules for Inorganic Compounds 11.7 LABORATORY SOLUTIONS Table 11.47 Concentration of Commonly Used Acids and Bases Table 11.48 Standard Stock Solutions 11.7.1 General Reagents, Indicators, and Special Solutions Table 11.49 TLV Concentration Limits for Gases and Vapors Table 11.50 Some Common Reactive and Incompatible Chemicals Table 11.51 Chemicals Recommended for Refrigerated Storage Table 11.52 Chemicals Which Polymerize or Decompose on Extended Refrigeration 11.8 SIEVES AND SCREENS Table 11.53 U.S. Standard Sieve Series 11.9 THERMOMETRY 11.9.1 Temperature and Its Measurement Table 11.54 Fixed Points in the ITS-90 11.10 THERMOCOUPLES Table 11.55 Thermoelectric Values in Millivolts at Fixed Points for Various Thermocouples Table 11.56 Type B Thermocouples: Platinum– 30% Rhodium Alloy vs. Platinum– 6% Rhodium Alloy Table 11.57 Type E Thermocouples: Nickel-Chromium Alloy vs. Copper-Nickel Alloy Table 11.58 Type J Thermocouples: Iron vs. Copper-Nickel Alloy Table 11.59 Type K Thermocouples: Nickel-Chromium Alloy vs. NickelAluminum Alloy Table 11.60 Type N Thermocouples: Nickel– 14.2% Chromium– 1.4% Silicon Alloy vs. Nickel– 4.4% Silicon– 0.1% Magnesium Alloy Table 11.61 Type R Thermocouples: Platinum– 13% Rhodium Alloy vs. Platinum Table 11.62 Type S Thermocouples: Platinum– 10% Rhodium Alloy vs. Platinum Table 11.63 Type T Thermocouples: Copper vs. Copper-Nickel Alloy 11.11 CORRECTION FOR EMERGENT STEM OF THERMOMETERS Table 11.64 Values of K for Stem Correction of Thermometers

11.89 11.89 11.92 11.93 11.94 11.95 11.96 11.97

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11.97 11.97 11.98 11.100 11.100 11.102 11.102 11.103 11.103 11.103 11.104 11.105 11.105 11.106 11.106 11.107 11.109 11.121 11.130 11.136 11.136 11.137 11.137 11.137 11.137 11.138 11.138 11.140 11.142 11.143 11.144 11.145 11.146 11.147 11.148 11.149 11.150 11.150

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PRACTICAL LABORATORY INFORMATION

11.1

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COOLING

TABLE 11.1 Cooling Mixtures The table below gives the lowest temperature that can be obtained from a mixture of the inorganic salt with finely shaved dry ice. With the organic substances, dry ice (⫺78⬚C) in small lumps can be added to the solvent until a slight excess of dry ice remains or liquid nitrogen (⫺196⬚C) can be poured into the solvent until a slush is formed that consists of the solid-liquid mixture at its melting point.

Substance

Quantity of substance, g

Quantity of water, mL

Temperature, ⬚C

100 75 110 36 50 66 85 100 100

94 100 100 100 100 100 100 81 70

⫺4.0 ⫺5.3 ⫺8.0 ⫺10.0 ⫺17.8 ⫺28 ⫺34 ⫺40.3 ⫺55

Ammonium nitrate Sodium nitrate Sodium thiosulfate 5-water Sodium chloride Sodium nitrate Sodium bromide Magnesium chloride Calcium chloride 6-water

Substance

Temperature, ⬚C

Substance

Ethylene glycol 1,2-Dichlorobenzene Carbon tetrachloride Bromobenzene Methoxybenzene Bis(2-ethoxyethyl) ether Chlorobenzene N-Methylaniline p-Cymene

⫺13 ⫺17 ⫺22.9 ⫺31 ⫺37 ⫺44 ⫺45 ⫺57 ⫺68

Acetone Ethyl acetate 2-Butanone Hexane Methanol Carbon disulfide Bromoethane Pentane 2-Methylbutane

Temperature, ⬚C ⫺77 ⫺84 ⫺87 ⫺95 ⫺98 ⫺112 ⫺119 ⫺130 ⫺160

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TABLE 11.2 Molecular Lowering of the Melting or Freezing Point Cryoscopic constants. The cryoscopic constant K ƒ gives the depression of the melting point ⌬T (in degrees Celsius) produced when 1 mol of solute is dissolved in 1000 g of a solvent. It is applicable only to dilute solutions for which the number of moles of solute is negligible in comparison with the number of moles of solvent. It is often used for molecular weight determinations. M2 ⫽

1000w2 Kƒ w1 ⌬T

where w1 is the weight of the solvent and w2 is the weight of the solute whose molecular weight is M2 . Compound Acetamide Acetic acid Acetone Ammonia Aniline Antimony(III) chloride Benzene Benzonitrile Benzophenone Bicyclohexane Biphenyl Borneol Bornylamine Butanedinitrile Camphene Camphoquinone D-(⫹)-Camphor Carbon tetrachloride o-Cresol p-Cresol Cyclohexane Cyclohexanol Cyclohexylcyclohexane Cyclopentadecanone cis-Decahydronaphthalene trans-Decahydronaphthalene Dibenz[de,kl]anthracene Dibenzyl ether 1,2-Dibromoethane Diethyl ether 1,2-Dimethoxybenzene N,N-Dimethylacetamide 2,2-Dimethyl-1-propanol Dimethyl sulfoxide 1,4-Dioxane

Kƒ 4.04 3.90 2.40 0.957 5.87 17.95 5.12 5.34 9.8 14.52 8.0 35.8 40.6 18.26 31.08 45.7 39.7 29.8 5.60 6.96 20.0 39.3 14.52 21.3 19.47 20.81 25.7 6.27 12.5 1.79 6.38 4.46 11.0 4.07 4.63

Compound Diphenylamine Diphenyl ether 1,2-Ethanediamine Ethoxybenzene Formamide Formic acid Glycerol Hexamethylphosphoramide N-Methylacetamide 2-Methyl-2-butanol Methylcyclohexane Methyl cis-9-octadecenoate 2-Methyl-2-propanol Naphthalene Nitrobenzene Octadecanoic acid 2-Oxohexamethyleneimine Phenol Pyridine Quinoline Succinonitrile Sulfuric acid 1,1,2,2-Tetrabromoethane 1,1,2,2-Tetrachloro1,2-difluoroethane Tetramethylene sulfone p-Toluidine Tribromomethane 1,3,3-Trimethyl-2-oxabicyclo[2.2.2.]octane Triphenylmethane Water p-Xylene

Kƒ 8.60 7.88 2.43 7.15 3.85 2.77 3.3 to 3.7 6.93 6.65 10.4 14.13 3.4 8.37 6.94 6.852 4.50 7.30 7.40 4.75 1.95 18.26 1.86 21.7 37.7 64.1 5.372 14.4 6.7 12.45 1.86 4.3

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DRYING AND HUMIDIFICATION

TABLE 11.3 Drying Agents

Most useful for

CaH 2d CaO CaSO4 Dow Desiccant 812e K 2CO3 KOH LiAlH4f Mg(ClO4 )2a MgO MgSO4 Molecular sieves: 4X 5X 9.5% Na-Pb alloyd Na2SO4 P2O5

Hydrocarbons, ethers, amines, esters, higher alcohols Ethers, esters, alcohols, amines Most organic substances Most materials Most materials except acids and phenols Amines Hydrocarbons Gas streams All but acidic compounds Most organic compounds ˚ Molecules with effective diameter ⬎4A ˚ Molecules with effective diameter ⬎5A Hydrocarbons, ethers Ketones, acids, alkyl and aryl halides Gas streams; not suitable for alcohols, amines, ketones, or amines Most organic amines Air and inert gas streams

Silica gel Sulfuric acid

d

a b May form explosive mixtures when contacting organic material. Explosive C2 H 2 formed. e f H 2 formed. Used as column drying of organic liquids. Strong reductant.

0.002–0.005 0.6–0.8 0.0007–0.003

0.2 0.17 0.12 0.56 0.15 (1 H2O) 0.30 (2 H2O) 0.85 0.31 0.07

0.1–0.2

c

1 ⫻ 10⫺5 0.01–0.003 0.005–0.07 (5–200 ppm)

175 (24 h) 140 1000 Impossible 250

0.0005–0.002 0.008 1–12 0.001 0.001 (For solvents only) 12 2 ⫻ 10⫺5

1.9 0.24 0.45 0.15–0.75 0.18 0.18 0.08 1.25 0.5

Impossible Difficult, 1000 225 No 158 Impossible Impossible 250 (high vacuum) 800 Not feasible 250 250 Impossible 150 Not feasible

0.002–0.07 0.003–0.008

0.2 Indefinite

200–350 Not feasible

0.16 0.01–0.9

Slow in drying action.

11.5

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Hydrocarbons Inert gas streams Basic gases: hydrocarbons, aldehydes, alcohols Ethers Inert organics

Regeneration, ⬚C

RIGHT

Al 2O3 Ba(ClO4 )2a BaO CaC2b CaCl2c

Grams water removed per gram of desiccant

(McGHP)

Drying agent

Residual water, mg H 2O per liter of dry air (25⬚C)

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SECTION 11

A saturated aqueous solution in contact with an excess of a definite solid phase at a given temperature will maintain constant humidity in an enclosed space. Table 11.4 gives a number of salts suitable for this purpose. The aqueous tension (vapor pressure, in millimeters of Hg) of a solution at a given temperature is found by multiplying the decimal fraction of the humidity by the aqueous tension at 100 percent humidity for the specific temperature. For example, the aqueous tension of a saturated solution of NaCl at 20⬚C is 0.757 ⫻ 17.54 ⫽ 13.28 mmHg and at 80⬚C it is 0.764 ⫻ 355.1 ⫽ 271.3 mmHg.

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TABLE 11.4 Solutions for Maintaining Constant Humidity % Humidity at Specified Temperatures (⬚C) Solid Phase K 2Cr2O7 K 2SO4 KNO3 KCl KBr NaCl NaNO3 NaNO2 NaBr · 2H 2O Na2Cr2O7 · 2H 2O Mg(NO3 )2 · 6H 2O K 2CO3 · 2H 2O MgCl 2 · 6H 2O KF · 2H 2O KC2 H 3O2 · 1.5H 2O LiCl · H 2O KOH 100% Humidity: Aqueous Tension (mm Hg)

10

20

25

30

76

97 93 85.0 84 75.7

58 57 47 34

66 57.9 55 55 44 33

98.0 97 92.5 84.3 80.7 75.3 73.8 65 57.7 54 52.9 42.8 33.0

24 13 13

23 12 9

22.5 10.2 8

33 27.4 22 12 7

9.21

17.54

23.76

31.82

98 95 88

96 91 84 74.9 72.8 63.0

52

40

60

96 88 81.7 79.6 74.7 71.5 61.5 52.4 53.6 49 42 32 22.8 20 11 6

96 82 80.7 79.0 74.9 67.5 59.3 49.9 55.2 43

55.32

149.4

30 21.0

80

79.5 79.3 76.4 65.5 58.9 50.0 56.0

22.8

11 5

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PRACTICAL LABORATORY INFORMATION

TABLE 11.5 Concentrations of Solutions of H 2SO4 , NaOH, and CaCl 2 Giving Specified Vapor Pressures and Percent Humidities at 25⬚C H 2SO4

Percent humidity

Aqueous tension, mmHg

Molality

Weight %

Molality

Weight %

Molality

Weight %

100 95 90 85 80 75 70 65 60 55 50 45 40 35 30 25 20 15 10 5

23.76 22.57 21.38 20.19 19.00 17.82 16.63 15.44 14.25 13.07 11.88 10.69 9.50 8.31 7.13 5.94 4.75 3.56 2.38 1.19

0.00 1.263 2.224 3.025 3.730 4.398 5.042 5.686 6.341 7.013 7.722 8.482 9.304 10.21 11.25 12.47 13.94 15.81 18.48 23.17

0.00 11.02 17.91 22.88 26.79 30.14 33.09 35.80 38.35 40.75 43.10 45.41 47.71 50.04 52.45 55.01 57.76 60.80 64.45 69.44

0.00 1.465 2.726 3.840 4.798 5.710 6.565 7.384 8.183 8.974 9.792 10.64 11.54 12.53 13.63 14.96 16.67 19.10 23.05

0.00 5.54 9.83 13.32 16.10 18.60 20.80 22.80 24.66 26.42 28.15 29.86 31.58 33.38 35.29 37.45 40.00 43.32 47.97

0.00 0.927 1.584 2.118 2.579 2.995 3.400 3.796 4.188 4.581 4.990 5.431 5.912 6.478 7.183

0.00 9.33 14.95 19.03 22.25 24.95 27.40 29.64 31.73 33.71 35.64 37.61 39.62 41.83 44.36

NaOH

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CaCl 2

Concentrations are expressed in percentage of anhydrous solute by weight. Source: Stokes and Robinson, Ind. Eng. Chem. 41:2013 (1949).

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TABLE 11.6 Relative Humidity from Wet and Dry Bulb Thermometer Readings Wet bulb depression, ⬚C Dry bulb temperature, ⬚C ⫺10 ⫺5 0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 35 40

0.5

1.0

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

6.0

21 29 36 41 46 50 53 56 58 61 63 64 66 67 69 70 72 74

13 22 29 35 40 44 48 51 54 57 59 61 62 64 65 67 69 72

5 14 22 29 35 39 43 47 50 53 55 57 59 61 62 64 67 69

7 16 24 29 34 39 42 46 49 51 54 56 58 59 61 64 67

12.0

13.0

14.0

15.0

7 12 17 20 24 27 30 32 35 37 39 40

6 11 15 19 22 25 28 30 33 35 36

6 10 14 18 21 24 26 29 31 33

5 10 13 17 20 23 25 27 29

Relative humidity, % 83 88 91 91 92 93 93 94 94 95 95 95 96 96 96 96 96 96 97 97

67 76 81 84 85 86 87 88 89 90 90 91 91 92 92 92 93 93 94 94

51 64 72 76 78 79 81 82 83 85 85 86 87 87 88 88 89 89 90 91

35 52 64 68 71 73 75 77 78 79 81 82 83 83 84 85 85 86 87 88

19 41 55 60 63 66 69 71 73 75 76 77 78 80 80 81 82 83 84 85

29 46 52 57 60 63 66 68 70 71 73 74 76 77 78 78 79 81 82

18 38 44 49 54 57 60 63 65 67 69 70 72 73 74 75 76 78 80

7 29 37 43 48 51 55 58 60 63 65 66 68 69 71 72 73 75 77

Wet bulb depression, ⬚C Dry bulb temperature, ⬚C

6.5

4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40

9 17 24 29 34 38 42 45 48 50 53 54 56 58 60 61 62 63 64

7.0

7.5

8.0

8.5

9.0

10.0

11.0

Relative humidity, %

11 19 24 29 34 38 41 44 47 49 51 53 55 57 58 59 61 62

5 14 20 25 30 34 38 41 44 46 49 51 52 54 56 57 58 59

8 15 21 26 30 34 37 40 43 46 48 50 51 53 54 56 57

10 16 22 26 30 34 37 40 43 45 47 49 51 52 54 54

6 12 18 23 27 31 34 37 40 42 44 46 48 50 51 53

5 10 15 20 24 28 31 34 37 39 41 43 45 47 48

8 14 18 22 26 29 32 35 37 39 41 43 44

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TABLE 11.7 Relative Humidity from Dew Point Readings Dew point reading, ⬚C Depression of dew point, ⬚C

⫺10

0.5 1.0 1.5 2.0 3.0 4.0 5.0 6.0 7.0 8.0 9.0 10.0 11.0 12.0 13.0 14.0 15.0 16.0 18.0 20.0 22.0 24.0 26.0 28.0 30.0

96 92 89 86 79 73 68 63 59 54 51 47 44 41 38 35 33 31 27 24 21 18 16 14 12

0

10

20

30

96 94 91 88 83 78 74 70 66 62 58 55 52 49 46 44 42 39 35 32

97 94 92 89 84 80 75 71 68 64 61 57

Relative humidity, % 96 93 89 87 81 75 70 66 61 57 53 50 47 44 41 38 36 34 30 26 23 21 18 16 14

96 94 90 88 82 77 72 68 63 60 56 53 49 47 44 41 39 37 33 29 26 23 21 19 17

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BOILING POINTS AND HEATING BATHS

TABLE 11.8 Organic Solvents Arranged by Boiling Points Name

BP, ⬚C

Name

Ethylene oxide Chloroethane Furan Methyl formate Diethyl ether Propylene oxide Pentane Bromoethane Dichloromethane Dimethoxymethane Carbon disulfide 1-Isopropoxy-2-propanol Ethyl formate Acetone Methyl acetate 1,1-Dichloroethane Dichloroethylene Chloroform Methanol Tetrahydrofuran Diisopropyl ether Hexane 1-Chloro-2-methylpropane 1,1,1-Trichloroethane 1,3-Dioxolane Carbon tetrachloride Ethyl acetate 1-Chlorobutane Ethanol 2-Butanone 2-Methyltetrahydrofuran Benzene Cyclohexane Propyl formate Acetonitrile 2-Propanol 1,1,-Dimethylethanol Cyclohexene Diisopropylamine 1,2-Dichloroethane Thiophene Trichloroethylene Isopropyl acetate 1-Bromo-2-methylpropane 2,5-Dimethylfuran Ethyl chloroformate Allyl alcohol 1,2-Dichloropropane

10.6 12.3 31.4 31.5 34.6 34.5 36.1 38.4 39.8 42.3 46.3 47.9 54.2 56.2 56.3 57.3 60.6 61.2 64.7 66.0 68.0 68.7 68.9 74.0 74– 75 76.7 77.1 77.9 78.3 79.6 80.0 80.1 80.7 80.9 81.6 82.4 82.4 83.0 83.5 83.7 84.2 87.2 88.2 91.5 93– 94 94 96.6 96.8

1-Propanol Heptane 1-Chloro-3-methylbutane Ethyl propionate 2-Butanol Formic acid Methylcyclohexane 1,4-Dioxane Nitromethane Propyl acetate 2-Pentanone 3-Pentanone 2-Methyl-2-butanol 1,1-Diethoxyethane Butyl formate 2-Methyl-1-propanol Toluene sec-Butyl acetate 1,1,2-Trichloroethane Nitroethane Pyridine 3-Pentanol 4-Methyl-2-pentanone 1-Chloro-2,3-epoxypropane 1-Butanol Acetic acid Isobutyl acetate 2-Pentanol 1-Bromo-3-methylbutane 1-Methoxy-2-propanol 2-Nitropropane Tetrachloroethylene Ethyl butyrate 3-Hexanone 2,4-Dimethyl-3-pentanone 2-Methoxyethanol Octane Butyl acetate Diethyl carbonate 2-Hexanone 1-Chloro-2-propanol 2-Chloroethanol 3-Methyl-1-penten-2-one 1-Nitropropane Chlorobenzene 1,2-Dibromoethane 4-Methyl-2-pentanol

BP, ⬚C 97.2 98.4 99 99.1 99.6 100.8 100.9 101.2 101.2 101.5 101.7 102.0 102.0 102.7 106.6 107.9 110.6 112.3 113.5 114.1 115.2 115.6 115.7 116.1 117.7 117.9 118.0 119.3 119.7 120.1 120.3 121.1 121.6 123 124 124.6 125.7 126.1 126.8 127.2 127.4 128.6 129.5 131.2 131.7 131.7 131.7

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11.11

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TABLE 11.8 Organic Solvents Arranged by Boiling Points (Continued) Name 3-Methyl-1-butanol Cyclohexylamine 2-Ethoxyethanol Ethylbenzene 1-Pentanol p-Xylene m-Xylene Acetic anhydride 2,4-Pentanedione Isopentyl acetate Dibutyl ether 4-Heptanone o-Xylene 2-Methoxyethyl acetate 1,1,2,2-Tetrachloroethane 3-Heptanone Tribromomethane Nonane 2-Heptanone Isopropylbenzene N,N-Dimethylformamide Methoxybenzene Ethyl lactate Cyclohexanone Bromobenzene 1,2,3-Trichloropropane 1-Hexanol Propylbenzene Cyclohexanol Bis(2-methoxyethyl)ether Isopentyl propionate 2-Heptanol Pentachloroethane 2-Furaldehyde 2,6-Dimethyl-4-heptanone 4-Hydroxy-4-methyl2-pentanone 2-Furanmethanol Ethoxybenzene 2-Butoxyethanol Diisopentyl ether Decane 1,3-Dichloro-2-propanol Cyclohexyl acetate 1-Heptanol Furfuryl acetate 1,3,3-Trimethyl2-oxabicyclo[2.2.2]octane 4-Isopropyl1-methylbenzene Isopentyl butyrate Bis(2-chloroethyl) ether

BP, ⬚C 132.0 134.8 134.8 136.2 138 138.4 139.1 140.0 140.6 142 142.4 143.7 144.4 144.5 146.3 147.8 149.6 150.8 151 152.4 153.0 153.8 154.5 155.7 156.2 156.9 157.5 159.2 161.1 160 160.2 160.4 160.5 161.8 168.1 169.2 170.0 170 170.2 173.4 174.2 174.3 174– 175 175.8 175– 177 177.4

177.1 178.6 178.8

Name 2-Octanol 1,2-Dichlorobenzene Ethyl acetoacetate Phenol 2-Ethyl-1-hexanol Aniline Benzyl ethyl ether Diethyl oxalate 1,2-Propanediol Bis(2-ethoxyethyl) ether Dimethyl sulfoxide 1,2-Ethanediol diacetate Benzonitrile 2,5-Hexanedione 2-(2-Methoxyethoxy)ethanol N,N-Dimethylaniline 1-Octanol 1,2-Ethanediol Diethyl malonate Methyl benzoate o-Toluidine p-Toluidine 2-(2-Ethoxyethoxy)ethanol Acetophenone 1,2-Dibutoxyethane 1-Phenylethanol m-Toluidine Benzyl alcohol Camphor 1,3-Butanediol 1,2,3,4-Tetrahydronaphthalene ␥-Valerolactone o-Chloroaniline Nitrobenzene Ethyl benzoate 3,5,5-Trimethylcyclohex-2-en-1-one Naphthalene 2-(2-Ethoxyethoxy)ethyl acetate Acetamide Methyl salicylate Diethyl maleate 1,4-Butanediol Propyl benzoate 1-Decanol Phenylacetonitrile Quinoline Tributyl borate Propylene carbonate

top of rh base of rh

BP, ⬚C 179 180.4 180.8 181.8 184.3 184.4 185.0 185.4 188 188.4 189.0 190.2 191.0 191.4 194.1 194.2 195.2 197.3 199.3 199.5 200.4 200.6 202 202.1 203.6 203.9 203.4 205.5 207 207.5 207.6 207– 208 208.8 210.8 212.4 215.2 217.7 218.5 221.2 223.0 225.3 230 231.2 230.2 233.5 237 238.5 240

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DEAN #37261

LEFT

(McGHP)

11.12

INTERACTIVE

top of rh base of rh

SECTION 11

cap height base of text

TABLE 11.8 Organic Solvents Arranged by Boiling Points (Continued) Name

BP, ⬚C

2-Phenoxyethanol Bis(2-hydroxyethyl) ether Dibutyl oxalate Butyl benzoate 1,2,3-Propanetriol triacetate 1-Chloronaphthalene Isopentyl benzoate trans-Ethyl cinnamate Bis[2-(methoxyethoxy)ethyl]ether 1-Methoxy-2-nitrobenzene

240 245 245.5 250 258– 259 259.3 262 271.0 275.3

Name Isopentyl salicylate 1-Bromonaphthalene Dimethyl o-phthalate 2,2⬘-(Ethylenedioxy)bisethanol Glycerol Diethyl o-phthalate Benzyl benzoate Dibutyl o-phthalate Dibutyl decanedioate

BP, ⬚C 277– 278 281.1 283.7 285 290 295 323.5 340.0 344– 345

277

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

11.13

PRACTICAL LABORATORY INFORMATION

top of rh base of rh cap height base of text

TABLE 11.9 Molecular Elevation of the Boiling Point Ebullioscopic constants. Molecular weights can be determined with the relation: M ⫽ Eb

1000 w2 w1 ⌬Tb

where ⌬Tb is the elevation of the boiling point brought about by the addition of w2 grams of solute to w1 grams of solvent and Eb is the ebullioscopic constant. In the column headed “Barometric correction” is the number of degrees for each millimeter of difference between the barometric reading and 760 mmHg to be subtracted from Eb if the pressure is lower, or added if higher, than 760 mm. In general, the effect is within experimental error if the pressure is within 10 mm of 760 mm. The ebullioscopic constant, a characteristic property of the solvent, may be calculated from the relation: Eb ⫽

RT 2b M ⌬vap H

where R is the molar gas constant, M is the molar mass of the solvent, and ⌬vap H the molar enthalpy (heat) of vaporization of the solvent.

Compound Acetic acid Acetic anhydride Acetone Acetonitrile Acetophenone Aniline Benzaldehyde Benzene Benzonitrile Bromobenzene Bromoethane 1-Butanol 2-Butanone cis-2-Butene-1,4-diol D-(⫹)-Camphor Carbon disulfide Carbon tetrachloride Chlorobenzene 1-Chlorobutane Chloroethane Chloroform Cyclohexane Cyclohexanol Decane 1,2-Dibromomethane 1,1-Dichloroethane 1,2-Dichloroethane Dichloromethane Diethyl ether Diethyl sulfide Dimethoxymethane N,N-Dimethylacetamide Dimethyl sulfide Dimethyl sulfoxide

Barometric correction

Eb , ⬚C kg · mol⫺1

0.0008

3.22 3.79 1.80 1.44 5.81 3.82 4.24 2.64 4.02 6.35 1.73 2.17 2.28 2.73 4.91 2.42 5.26 4.36 3.13 1.77 3.80 2.92 3.5 6.10 6.01 3.13 3.27 2.42 2.20 3.14 2.12 3.22 1.85 3.22

0.0004

0.0009 0.0007 0.0016

0.0015 0.0006 0.0013 0.0011

0.0009 0.0007

0.0016

0.0005

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DEAN #37261

LEFT

(McGHP)

11.14

INTERACTIVE

top of rh base of rh

SECTION 11

cap height base of text

TABLE 11.9 Molecular Elevation of the Boiling Point (Continued)

Compound 1,4-Dioxane Ethanol Ethoxybenzene Ethyl acetate Ethylene glycol Formic acid Glycerol Heptane Hexane 2-Hydroxybenzaldehyde Iodoethane Iodomethane 4-Isopropyl-1-methylbenzene Methanol Methoxybenzene Methyl acetate N-Methylaniline 2-Methyl-2-butanol 3-Methyl-1-butanol 3-Methylbutyl acetate N-Methylformamide Methyl formate 2-Methyl-1-propanol 2-Methyl-2-propanol Naphthalene Nitrobenzene Nitroethane Nitromethane Octane 1-Octanol Pentyl acetate Phenol Piperidine Propanoic acid 1-Propanol 2-Propanol Propionitrile Pyridine Pyrrole Pyrrolidine Quinoline Tetrachloroethylene Tetrachloromethane 1,2,3,4-Tetrahydronaphthalene Toluene p-Toluidine Trichloroethylene Trichloromethane 1,1,2-Trichloro-1,2,2-trifluoroethane Triethylamine Water o-Xylene

Barometric correction

0.0003 0.0007

0.0008

0.0002 0.0005

0.0014

0.0009

0.0008

0.0009

0.0001

Eb , ⬚C kg · mol⫺1 3.00 1.22 4.90 2.82 2.26 2.36 6.52 3.62 2.90 5.87 5.27 4.31 5.92 0.86 4.20 2.21 4.3 2.64 2.88 4.83 2.2 1.66 2.14 1.99 5.94 5.24 2.46 2.09 4.39 5.06 4.71 3.54 3.21 3.27 1.66 1.58 1.97 2.83 2.33 2.32 5.62 6.18 5.26 5.58 3.40 4.51 4.52 3.80 5.93 3.57 0.512 4.25

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

11.15

PRACTICAL LABORATORY INFORMATION

cap height base of text

TABLE 11.10 Substances Which Can Be Used for Heating Baths Melting point, ⬚C

Boiling point, ⬚C

Useful range, ⬚C

Flash point, ⬚C

Water Silicone oil

0 ⫺50

100 —

0– 100 30– 250

None 315

Triethylene glycol Glycerol Paraffin Dibutyl o-phthalate

⫺7 18 50 ⫺35

285 290 — 340

0– 250 ⫺20 to 260 60– 300 150– 320

165 160 199 171

Medium

top of rh base of rh

Comments Ideal Somewhat viscous at low temperature Noncorrosive Water-soluble, nontoxic Flammable Generally used

short standard long

DEAN #37261

11.4

SEPARATION METHODS

(McGHP)

TABLE 11.11 Solvents of Chromatographic Interest

36 69 99 174 81 49 101 30 46 77 78 98 144 68 35 111 47 132 80 38

e⬚ (SiO2 )

0.0 0.0 ⫺0.05

0.14 0.14

0.25

e⬚ (Al 2O3 ) ⫺0.25 0.0 0.0 0.01 0.04 0.04 0.05 0.06 0.08 0.15 0.18 0.26 0.26 0.26 0.28 0.29 0.29 0.30 0.40 0.32 0.37

Viscosity, mN · s · m⫺2 (20⬚C)

0.2415⬚C 0.31 0.50 0.93 0.98 0.44 0.240⬚C 0.36 0.97 0.43 0.58 0.81 0.3825⬚C 0.33 0.59 0.35 0.80 0.65 0.40

Refractive index (20⬚C) 1.25 1.358 1.375 1.392 1.412 1.426 1.407 1.411 1.371 1.626 1.466 1.402 1.412 1.505 1.369 1.378 1.497 1.389 1.525 1.501 1.424

UV cutoff, nm

210 210 215 210 210 210

380 265 220 225 290 220 225 286 225

INTERACTIVE

Fluoroalkanes Pentane Hexane 2,2,4-Trimethylpentane Decane Cyclohexane Cyclopentane Diisobutylene 1-Pentene Carbon disulfide Carbon tetrachloride 1-Chlorobutane 1-Chloropentane o-Xylene Diisopropyl ether 2-Chloropropane Toluene 1-Chloropropane Chlorobenzene Benzene Bromoethane

Solvent strength parameter

LEFT

Solvent

Boiling point, ⬚C

280

11.16

top of page

short standard

base of DF

e⬚ (SiO2 ) 0.38 0.26

0.47 0.49 0.38

0.50

e⬚ (Al 2O3 )

Viscosity, mN · s · m⫺2 (20⬚C)

Refractive index (20⬚C)

0.38 0.38 0.40 0.42 0.43 0.45 0.49 0.51 0.53 0.56 0.56 0.58 0.60 0.61 0.62 0.62 0.63 0.64 0.65 0.71 0.74 0.82 0.82 0.88 0.95 1.11 large large

0.25 0.45 0.57 0.44 0.4215⬚C 0.55 0.80 0.4215⬚C 0.8025⬚C 0.32 1.4415⬚C 0.45 0.4815⬚C 4.1 2.47 4.40 0.33 0.67 0.37 0.97 3.1525⬚C 2.25 2.50 1.20 0.59 21.8 1.23 1.00

1.353 1.443 1.443 1.425 1.396 1.407 1.445 1.379 1.402 1.359 1.420 1.372 1.362 1.410 1.478 1.586 1.386 1.394 1.344 1.510 1.420 1.386 1.377 1.361 1.328 1.432 1.372 1.333

UV cutoff, nm 218 290 245 235 335 220 228 330 380 330 215 255 260 210 265 275 380 190 330 220 210 210 210 210 210 260 191

11.17

INTERACTIVE

35 92 62 41 116 66 84 80 131 56 101 77 56 138 189 184 56 101 82 115 170 97 82 78 65 198 118 100

Solvent strength parameter

RIGHT

Diethyl ether Diethyl sulfide Chloroform Dichloromethane 4-Methyl-2-pentanone Tetrahydrofuran 1,2-Dichloroethane 2-Butanone 1-Nitropropane Acetone 1,4-Dioxane Ethyl acetate Methyl acetate 1-Pentanol Dimethyl sulfoxide Aniline Diethylamine Nitromethane Acetonitrile Pyridine 2-Butoxyethanol 1-Propanol 2-Propanol Ethanol Methanol Ethylene glycol Acetic acid Water

Continued

(McGHP)

Solvent

Boiling point, ⬚C

DEAN #37261

TABLE 11.11 Solvents of Chromatographic Interest

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base of DF

DEAN #37261

LEFT

(McGHP)

11.18

INTERACTIVE

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SECTION 11

cap height base of text

TABLE 11.12 Solvents Having the Same Refractive Index and the Same Density at 25⬚C Refractive index

Density, g/mL

Solvent 1

Solvent 2

1

2

1

2

Acetone Ethyl formate Ethanol 2,2-Dimethylbutane 2-Methylpentane Isopropyl acetate 3-Butanone Butyraldehyde Dipropyl ether Propyl acetate Propyl acetate Butyronitrile Ethyl propionate 1-Propanol Isobutyl formate 1-Chloropropane Butyl formate Methyl butyrate Butyl acetate 4-Methyl-2-pentanone 4-Methyl-2-pentanone 2-Methyl-1-propanol 2-Methyl-1-propanol 2-Butanol 2-Hexanone Pentanonitrile 2-Chlorobutane Butyric acid 1-Butanol 1-Chloro-2-methylpropane 1-Chloro-2-methylpropane Methyl methacrylate Triethylamine Butylamine Isobutyl butyrate 1-Nitropropane Pentyl acetate Pentyl acetate Dodecane 1-Chlorobutane Isopentanoic acid Dipropylamine 2-Pentanol 3-Methyl-1-butanol 3-Methyl-1-butanol Hexanonitrile Hexanonitrile Hexanonitrile 4-Heptanone

Ethanol Methyl acetate Propionitrile 2-Methylpentane Hexane 2-Chloropropane Butyraldehyde Butyronitrile Butyl ethyl ether Ethyl propionate 1-Chloropropane 2-Methyl-2-propanol 1-Chloropropane 2-Pentanone 1-Chloropropane Butyl formate Methyl butyrate 2-Chlorobutane 2-Chlorobutane Pentanonitrile 1-Butanol Pentanonitrile 2-Hexanone 2,4-Dimethyl-3-pentanone 1-Butanol 2,4-Dimethyl-3-pentanone Isobutyl butyrate 2-Methoxyethanol 3-Methyl-2-pentanone Isobutyl butyrate Pentyl acetate 3-Methyl-2-pentanone 2,2,3-Trimethylpentane Dodecane 1-Chlorobutane Propionic anhydride 1-Chlorobutane Tetrahydrofuran Dipropylamine Tetrahydrofuran 2-Ethoxyethanol Cyclopentane 4-Heptanone Hexanonitrile 4-Heptanone 4-Heptanone 1-Pentanol 2-Methyl-1-butanol 1-Pentanol

1.357 1.358 1.359 1.366 1.369 1.375 1.377 1.378 1.379 1.382 1.382 1.382 1.382 1.383 1.383 1.386 1.387 1.392 1.392 1.394 1.394 1.394 1.394 1.395 1.395 1.395 1.395 1.396 1.397 1.397 1.397 1.398 1.399 1.399 1.399 1.399 1.400 1.400 1.400 1.401 1.402 1.403 1.404 1.404 1.404 1.405 1.405 1.405 1.405

1.359 1.360 1.363 1.369 1.372 1.376 1.378 1.382 1.380 1.382 1.386 1.385 1.386 1.387 1.386 1.387 1.391 1.395 1.395 1.395 1.397 1.395 1.395 1.399 1.397 1.399 1.399 1.400 1.398 1.399 1.400 1.398 1.401 1.400 1.401 1.400 1.400 1.404 1.400 1.404 1.405 1.404 1.405 1.405 1.405 1.405 1.408 1.409 1.408

0.788 0.916 0.786 0.644 0.649 0.868 0.801 0.799 0.753 0.883 0.883 0.786 0.888 0.806 0.881 0.890 0.888 0.875 0.877 0.797 0.797 0.798 0.798 0.803 0.810 0.795 0.868 0.955 0.812 0.872 0.872 0.795 0.723 0.736 0.860 0.995 0.871 0.871 0.746 0.871 0.923 0.736 0.804 0.805 0.805 0.801 0.801 0.801 0.813

0.786 0.935 0.777 0.649 0.655 0.865 0.799 0.786 0.746 0.888 0.890 0.781 0.890 0.804 0.890 0.888 0.875 0.868 0.868 0.795 0.812 0.795 0.810 0.805 0.812 0.805 0.860 0.960 0.808 0.860 0.871 0.808 0.712 0.746 0.875 1.007 0.881 0.885 0.736 0.885 0.926 0.740 0.813 0.801 0.813 0.813 0.810 0.815 0.810

short standard long

DEAN #37261

(McGHP)

RIGHT

INTERACTIVE

11.19

PRACTICAL LABORATORY INFORMATION

cap height base of text

TABLE 11.12 Solvents Having the Same Refractive Index and the Same Density at 25⬚C (Continued) Refractive index Solvent 1 2-Ethoxyethanol 2-Heptanone 2-Heptanone 2-Heptanone 2-Pentanol 1-Pentanol 2-Methyl-1-butanol Isopentyl isopentanoate Dipentyl ether 2,4-Dimethyldioxane 2,4-Dimethyldioxane Diethyl malonate 3-Chloropentene 2-Octanone 2-Octanone 3-Octanone 3-Methyl-2-heptanone 3-Methyl-2-heptanone 1-Hexanol Dibutylamine Allylamine Butyrolactone Butyrolactone 2-Chloromethyl-2propanol N-Methylmorpholine 1,3-Propanediol Methyl salicylate Methyl salicylate 1-Chlorodecane Diethylene glycol Diethylene glycol Formamide 2-Methylmorpholine 2-Methylmorpholine Dipropylene glycol monoethyl ether 1-Amino-2-methyl-2pentanol 2-Propylcyclohexanone Carbon tetrachloride N-Butyldiethanolamine D-␣-Pinene Propylbenzene Propylbenzene

Solvent 2

top of rh base of rh

Density, g/mL

1

2

1

2

Pentanoic acid 1-Pentanol 2-Methyl-1-butanol Dipentyl ether 3-Isopropyl-2-pentanone Dipentyl ether Dipentyl ether Allyl alcohol 2-Octanone 3-Chloropentene Hexanoic acid Ethyl cyanoacetate Octanoic acid 1-Hexanol Octanonitrile 3-Methyl-2-heptanone 1-Hexanol Octanonitrile Octanonitrile Allylamine Methylcyclohexane 1,3-Propanediol Diethyl maleate Diethyl maleate

1.405 1.406 1.406 1.406 1.407 1.408 1.409 1.410 1.410 1.412 1.412 1.412 1.413 1.414 1.414 1.414 1.415 1.415 1.416 1.416 1.419 1.434 1.434 1.436

1.406 1.408 1.409 1.410 1.409 1.410 1.410 1.411 1.414 1.413 1.415 1.415 1.415 1.416 1.418 1.416 1.416 1.418 1.418 1.419 1.421 1.438 1.438 1.438

0.926 0.811 0.811 0.811 0.804 0.810 0.815 0.853 0.799 0.935 0.935 1.051 0.932 0.814 0.814 0.830 0.818 0.818 0.814 0.756 0.758 1.051 1.051 1.059

0.936 0.810 0.815 0.799 0.808 0.799 0.799 0.847 0.814 0.932 0.923 1.056 0.923 0.814 0.810 0.818 0.814 0.810 0.810 0.758 0.765 1.049 1.064 1.064

Dibutyl decanedioate Diethyl maleate Diethyl sulfide 1-Butanethiol Mesityl oxide Formamide Ethylene glycol diglycidyl ether Ethylene glycol diglycidyl ether Cyclohexanone 1-Amino-2-propanol Tetrahydrofurfuryl alcohol

1.436 1.438 1.438 1.438 1.441 1.445 1.445

1.440 1.438 1.442 1.442 1.442 1.446 1.447

0.924 1.049 0.836 0.836 0.862 1.128 1.128

0.932 1.064 0.831 0.837 0.850 1.129 1.134

1.446

1.447

1.129

1.134

1.446 1.446 1.446

1.448 1.448 1.450

0.951 0.951 1.043

0.943 0.961 1.050

2-Butylcyclohexanone

1.449

1.453

0.904

0.901

4-Methylcyclohexanol 4,5-Dichloro-1,3dioxolane-2-one Cyclohexanol trans-Decahydronaphthalene p-Xylene Toluene

1.452 1.459

1.454 1.461

0.923 1.584

0.908 1.591

1.461 1.464

1.465 1.468

0.965 0.855

0.968 0.867

1.490 1.490

1.493 1.494

0.858 0.858

0.857 0.860

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DEAN #37261

LEFT

(McGHP)

11.20

INTERACTIVE

top of rh base of rh

SECTION 11

cap height base of text

TABLE 11.12 Solvents Having the Same Refractive Index and the Same Density at 25⬚C (Continued) Refractive index Solvent 1 Phenyl 1-hydroxyphenyl ether Phenetole 2-Furanmethanol m-Cresol

Solvent 2 1,3-Dimorpholyl-2propanol Pyridine Thiophene Benzaldehyde

Density, g/mL

1

2

1

2

1.491

1.493

1.081

1.094

1.505 1.524 1.542

1.507 1.526 1.544

0.961 1.057 1.037

0.978 1.059 1.041

short standard long

Temp., ⬚C Stationary phase

Chemical type

Similar stationary phases

Min

Max

McReynolds’ constants x’

y’

z’

u’

s’

USP code

(McGHP)

⌺

Boiling-point separation of broad molecular weight range of compounds; nonpolar phases Squalane

2,6,10,15,19,23-Hexamethyltetracosane

20

150

0 9

5

2

6

11

33

50

300

32

22

15

32

42

143

⫺60

320

4

58

43

56

38

199

0

350

17

57

45

67

43

229

Paraffin oil Apiezon威 L SPB-1

Poly(dimethylsiloxane)

SA-1, DB-1

SP娃-2100

Poly(dimethylsiloxane)

DC-200, SE 30, UC W98, DC 200

0

0

0

0

0

G9

100

350

16

55

44

65

42

227

G2

Methylsiloxane fluid

20

350

17

57

45

67

43

234

G1

SPB-5

1% Vinyl, 5% phenyl methyl polysiloxane

SA-5, DB-5

⫺60

320

19

74

64

93

62

312

SE-54

1% Vinyl, 5% phenyl methyl polysiloxane

PTE-5

50

300

19

74

64

93

62

312

G 36

SE-52

5% Phenyl methyl polysiloxane

50

300

32

72

65

98

67

334

G 27

OV-73

5.5% Phenyl methyl polysiloxane

0

325

40

86

76

114

85

401

G 27

OV-3

Poly(dimethyldiphenylsiloxane); 90%:10%

0

350

44

86

81

124

88

423

Dexsil威 300

Carborane 9 methyl silicone

50

450

47

80

103

148

96

474

Dexsil威 400

Carborane 9 methylphenyl silicone

50

400

72

108

118

166

123

587

G 33

11.21

INTERACTIVE

Methylsiloxane gum

OV-101

RIGHT

OV-1

SP-400

DEAN #37261

TABLE 11.13 McReynolds’ Constants for Stationary Phases in Gas Chromatography

top of page

short standard

base of DF

Temp., ⬚C Stationary phase

Similar stationary phases

Chemical type

Min

Max

McReynolds’ constants x’

y’

z’

u’

s’

⌺

USP code

OV-7

20% Phenyl methyl polysiloxane

DC 550

SPB-20

20% Phenyl methyl polysiloxane

SPB-35, SPB-1701, DB-1301

Di-(2-ethylhexyl)sebacate DC 550

25% Phenyl methyl polysiloxane

(McGHP)

Boiling-point separation of broad molecular weight range of compounds; nonpolar phases (continued)

DEAN #37261

TABLE 11.13 McReynolds’ Constants for Stationary Phases in Gas Chromatography (Continued)

0

350

69

113

111

171

128

592

⬍20

300

67

116

117

174

131

605

⫺20

125

72

168

108

180

125

653

G 11

20

225

81

124

124

189

145

663

G 28

G 24

Unsaturated hydrocarbons and other compounds of intermediate polarity Diisodecyl phthalate

20

150

84

173

137

218

155

767

0

350

102

142

145

219

178

786

67

170

152

228

171

789

35% Phenyl methyl polysiloxane

OV-1701

Vinyl methyl polysiloxane

SPB-1701, SA-1701, DB-1701

0

250 275

115

194

122

204

202

837

G 37

SP-2250

Poly(phenylmethylsiloxane); 50% phenyl

OV-17, DB-17

0

375

119

158

162

243

202

884

G3

Dexsil威 410

Carborane— methylcyano ethyl silicone

50

400

72

286

174

249

171

952

UCON威 LB-550-X

Polyalkylene glycol

20

UCON LB-1880-X

Polyalkylene glycol

Poly-I 110

200

118

271

158

243

206

996

200

123

275

161

249

212

1020

G 18

275

115

331

144

263

214

1072

G 10

INTERACTIVE

Poly-A 103

LEFT

OV-11

11.22

top of page

short standard

base of DF

TABLE 11.13 McReynolds’ Constants for Stationary Phases in Gas Chromatography (Continued) Temp., ⬚C Stationary phase

Chemical type

Similar stationary phases

Min

Max

McReynolds’ constants x’

y’

Unsaturated hydrocarbons and other compounds of intermediate polarity Poly(diphenyldimethylsiloxane); 65%:35%

0

Di(2-ethylhexyl) phthalate OV-25

Poly(diphenyldimethylsiloxane); 75%:25%

0

u’

s’

⌺

USP code

(continued)

350

160

188

191

283

253

1075

150

135

254

213

320

235

1157

G 22

350

178

204

208

305

280

1175

G 17

(McGHP)

Moderately polar compounds DC QF-1

0

250

144

233

355

463

305

1500

0

275

146

238

358

468

310

1520

Poly(trifluoropropylmethylsiloxane)

0

275

149

240

363

478

315

1545

UCON-50-HB2000

Polyalkylene glycol

0

200

202

394

253

392

341

1582

Triton威 X-100

Octylphenoxy polyethoxy ethanol

0

190

203

399

268

402

362

1634

UCON 50-HB5100

Polyglycol

0

200

214

418

278

421

375

1706

XE-60

Poly(cyanoethylphenylmethylsiloxane)

0

250

204

381

340

493

367

1785

G 26

OV-225

25% Cyanopropyl 25% phenyl methyl polysiloxane

0

265

228

369

338

492

386

1813

G 19

Ipegal CO-880

Nonylphenoxypoly(ethyleneoxy)ethanol

100

200

259

461

311

482

426

1939

G 31

Triton威 X-305

Octylphenoxy polyethoxy ethanol

200

250

262

467

314

488

430

1961

OV-210

50% Trifluoropropylmethylpolysiloxane

OV-215

SP-2401, DB-210

G6

RIGHT

DB-225, DB-23

DEAN #37261

OV-22

z’

INTERACTIVE

11.23

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TABLE 11.13 McReynolds’ Constants for Stationary Phases in Gas Chromatography (Continued)

Stationary phase

Chemical type

Min

McReynolds’ constants

Max

x’

y’

z’

u’

s’

⌺

USP code

Polar compounds Neopentylglycol succinate

50

230

272

469

366

539

474

2120

G 21

Carbowax 20MTPA

Polyethyleneglycol ⫹ terephthalic acid

60

250

321

367

368

573

520

2149

G 25

Supelcowax娃 10

Polyethyleneglycol ⫹ terephthalic acid

50

280

305

551

360

562

484

2262

SP-1000

Polyethyleneglycol ⫹ terephthalic acid

60

220

304

552

359

549

498

2262

Carbowax 20M

Polyethyleneglycol

25

275

322

536

368

572

510

2308

311

572

374

572

520

2349

DB-WAX, SA-WAX

SP-2300 SP-1000, FFAP, OV-351

Carbowax 3350

Formerly Carbowax 4000

60

200

325

551

375

582

520

2353

SP-1000

50

270

335

552

382

583

540

2392

25

275

316

495

446

637

530

2424

0

250

319

495

446

637

531

2428

OV-351

Polyethyleneglycol ⫹ nitroterephthalic acid

SP-2300

36% Cyanopropyl

Silar 5 CP

50% Cyanopropyl phenyl silicone

SP-2300

G 16

G 15

G7

LEFT

Nukol娃

(McGHP)

Hi-EFF-3BP

DEAN #37261

Temp., ⬚C Similar stationary phases

INTERACTIVE

11.24

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DEAN #37261

TABLE 11.13 McReynolds’ Constants for Stationary Phases in Gas Chromatography (Continued) Temp., ⬚C Stationary phase

Chemical type

Similar stationary phases

McReynolds’ constants x’

y’

z’

u’

s’

⌺

USP code

50

250

340

580

397

602

627

2546

G 35

20

230

386

555

472

674

656

2744

G 21

50

175

371

639

453

666

641

2770

G 14

402

629

520

744

623

2918

(McGHP)

Max

Min Polar compounds

FFAP Hi-EFF-10BP

Phenyldiethanolamine succinate

Carbowax 1450

Formerly 1540

SP-2380 SP-2310

55% Cyanopropyl

Silar 7 CP

25

275

440

637

605

840

670

3192

SP-2330

68% Cyanopropyl

SP-2331, SH-60

25

275

490

725

630

913

778

3536

Silar 9 CP

90% Cyanopropyl phenyl

50

250

489

725

631

913

778

3536

G8

Hi-EFF-1BP

Diethyleneglycol succinate

20

200

499

751

593

840

860

3543

G4

SP-2340

75% Cyanopropyl phenyl

OV-275, SH-80

⬍25

275

520

757

659

942

800

3678

Silar 10 CP

100% Cyanopropyl silicone

SP-2340

25

275

523

757

659

942

801

3682

THEED

Amino alcohol

OV-275

Dicyanoallylsilicone

125

463

942

626

801

893

3725

250

629

872

763

110

849

4219

653

590

627

652

RIGHT

Absolute index values on squalane for reference compounds:

0 25

G5

699

INTERACTIVE

Note: USP code is the United States Pharmacopeia designation.

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SECTION 11

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McReynolds’ Constants

The Kovats retention indices (R.I.) indicate where compounds will appear on a chromatogram with respect to unbranched alkanes injected with the sample. By definition, the R.I. for pentane is 500, for hexane is 600, for heptane is 700, and so on, regardless of the column used or the operating conditions, although the exact conditions and column must be specified, such as liquid loading, particular support used, and any pretreatment. For example, suppose that on a 20% squalane column at 100⬚C, the retention times for hexane, benzene, and octane are found to be 15, 16, and 25 min, respectively. On a graph of ln t⬘R (naperian logarithm of the adjusted retention time) of the alkanes versus their retention indices, a R.I. of 653 for benzene is read off the graph. The number 653 for benzene (see last line of Table 11.13 in the column headed “1” under “Reference compounds”) means that it elutes halfway between hexane and heptane on a logarithmic time scale. If the experiment is repeated with a dinonyl phthalate column, the R.I for benzene is found to be 736 (lying between heptane and octane), which implies that dinonyl phthalate will retard benzene slightly more than squalane will; that is, dinonyl phthalate is slightly more polar than squalane by ⌬I ⫽ 83 units (the entry in Table 11.13 for dinonyl phthalate in the column headed “1” under “Reference compounds”). The difference gives a measure of solute-solvent interaction due to all intermolecular forces other than London dispersion forces. The latter are the principal solute-solvent effects with squalane. TABLE 11.14 Characteristics of Selected Supercritical Fluids

Fluid

Critical temperature, K (⬚C)

Critical pressure, atm (psi)

Ammonia Argon Benzene Butane Carbon dioxide Carbon disulfide Chlorotrifluoromethane 2,2-Dimethylpropane Ethane Fluoromethane Heptane Hexane Hydrogen sulfide Krypton Methane Methanol 2-Methylpropane Nitrogen Nitrogen(I) oxide Pentane Propane Sulfur dioxide Sulfur hexafluoride Trichloromethane Trifluoromethane Water Xenon

406 (133) 151 (⫺122) 562 (289) 425 (125) 304 (31) 552 (279) 379 (106) 434 (161) 305 (32) 318 (45) 540 (267) 507 (234) 373 (100) 209 (⫺64) 191 (⫺82) 513 (240) 408 (65) 126 (⫺147) 310 (37) 470 (197) 470 (197) 431 (158) 319 (46) 536 (263) 299 (26) 647 (374) 290 (17)

111.3 (1636) 48.1 (707) 48.3 (710) 37.5 (551) 72.8 (1070) 78.0 (1147) 40 (588) 31.6 (464) 48.2 (706) 58.0 (853) 27.0 (397) 29.3 (431) 88.2 (1296) 54.3 (798) 45.4 (667) 79.9 (1175) 36.0 (529) 33.5 (492) 71.5 (1051) 33.3 (490) 41.9 (616) 77.8 (1144) 37.1 (545) 54.9 (807) 47.7 (701) 217.6 (3199) 57.6 (847)

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PRACTICAL LABORATORY INFORMATION

INTERACTIVE

11.27

Now the overall effects due to hydrogen bonding, dipole moment, acid-base properties, and molecular configuration can be expressed as

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冘 ⌬I ⫽ ax⬘ ⫹ by⬘ ⫹ cz⬘ ⫹ du⬘ ⫹ es⬘ where x⬘ ⫽ ⌬I for benzene (the column headed “1” in Table 11.13, intermolecular forces typical of aromatics and olefins), y⬘ ⫽ ⌬I for 1-butanol (the column headed “2” in Table 11.13, electron attraction typical of alcohols, nitriles, acids, and nitro and alkyl monochlorides, dichlorides and trichlorides), z⬘ ⫽ ⌬I for 2-pentanone (the column headed “3” in Table 11.13, electron repulsion typical of ketones, ethers, aldehydes, esters, epoxides, and dimethylamino derivatives), u⬘ ⫽ ⌬I for 1-nitropropane (the column headed “4” in Table 11.13, typical of nitro and nitrile derivatives), and s⬘ ⫽ ⌬I for pyridine (or dioxane) (the column headed “5” in Table 11.13).

11.4.2

Chromatographic Behavior of Solutes

11.4.2.1 Retention Behavior. On a chromatogram the distance on the time axis from the point of sample injection to the peak of an eluted component is called the uncorrected retention time tR . The corresponding retention volume is the product of retention time and flow rate, expressed as volume of mobile phase per unit time: VR ⫽ tRFc The average linear velocity u of the mobile phase in terms of the column length L and the average linear velocity of eluent tM (which is measured by the transit time of a nonretained solute) is u⫽

L tM

The adjusted retention time t⬘R is given by t⬘R ⫽ tR ⫺ tM When the mobile phase is a gas, a compressibility factor j must be applied to the adjusted retention volume to give the net retention volume: VN ⫽ jV ⬘R The compressibility factor is expressed by j⫽

3[(Pi /Po)2 ⫺ 1] 2[(Pi /Po)3 ⫺ 1]

where Pi is the carrier gas pressure at the column inlet and Po that at the outlet.

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SECTION 11

11.4.2.2 Partition Ratio. The partition ratio is the additional time a solute band takes to elute, as compared with an unretained solute (for which k⬘ ⫽ 0), divided by the elution time of an unretained band: k⬘ ⫽

cap height base of text

tR ⫺ tM VR ⫺ VM ⫽ tM VM

Retention time may be expressed as tR ⫽ tM(1 ⫹ k⬘) ⫽

L (1 ⫹ k⬘) u

11.4.2.3 Relative Retention. The relative retention ␣ of two solutes, where solute 1 elutes before solute 2, is given variously by

␣⫽

k⬘2 V⬘R,2 t⬘R,2 ⫽ ⫽ k⬘1 V⬘R,1 t⬘R,1

The relative retention is dependent on (1) the nature of the stationary and mobile phases and (2) the column operating temperature. 11.4.2.4 Column Efficiency. Under ideal conditions the profile of a solute band resembles that given by a Gaussian distribution curve (Fig. 11.1). The efficiency of a chromatographic system is expressed by the effective plate number Neff , defined from the chromatogram of a single band, Neff ⫽

L ⫽ 16 H

冉 冊 t⬘R Wb

2

冉 冊 t⬘R W1/2

⫽ 5.54

2

where L is the column length, H is the plate height, t⬘R is the adjusted time for elution of the band center, Wb is the width at the base of the peak (Wb ⫽ 4␴) as determined from the intersections of tangents to the inflection points with the baseline, and W1/2 is the width at half the peak height. Column efficiency, when expressed as the number of theoretical plates Ntheor uses the uncorrected retention time in the foregoing expression. The two column efficiencies are related by Neff ⫽ Ntheor

冉

k⬘ k⬘ ⫹ 1

冊

2

11.4.2.5 Band Asymmetry. The peak asymmetry factor AF is often defined as the ratio of peak half-widths at 10% of peak height, that is, the ratio b/a, as shown in Fig. 11.2. When the asymmetry ratio lies outside the range 0.95–1.15 for a peak of k⬘ ⫽ 2, the effective plate number should be calculated from the expression N⫽

41.7(t⬘/W R 0.1) (a/b) ⫹ 1.25

11.4.2.6 Resolution. The degree of separation or resolution, Rs, of two adjacent peaks is defined as the distance between band peaks (or centers) divided by the average bandwidth using Wb , as shown in Fig. 11.3. Rs ⫽

tR,2 ⫺ tR,1 0.5(W2 ⫹ W1)

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RIGHT

11.29

INTERACTIVE

FIGURE 11.1 Profile of a solute band.

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11.30

INTERACTIVE

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SECTION 11

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FIGURE 11.2 Band asymmetry.

For reasonable quantitative accuracy, peak maxima must be at least 4␴ apart. If so, then Rs ⫽ 1.0, which corresponds approximately to a 3% overlap of peak areas. A value of Rs ⫽ 1.5 (for 6␴) represents essentially complete resolution with only 0.2% overlap of peak areas. These criteria pertain to roughly equal solute concentrations. The fundamental resolution equation incorporates the terms involving the thermodynamics and kinetics of the chromatographic system: Rs ⫽

冉 冊冉

1 ␣⫺1 4 ␣

k⬘ 1 ⫹ k⬘

冊冉 冊 L H

1/2

Three separate factors affect resolution: (1) a column selectivity factor that varies with ␣, (2) a capacity factor that varies with k⬘ (taken usually as k2), and (3) an efficiency factor that depends on the theoretical plate number.

FIGURE 11.3 Definition of resolution.

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PRACTICAL LABORATORY INFORMATION

11.4.2.7

INTERACTIVE

Time of Analysis. The retention time required to perform a separation is given by tR ⫽ 16Rs2

冉 冊冋 ␣ ␣⫺1

2

(1 ⫹ k⬘)3 (k⬘)2

top of rh base of rh cap height base of text

册冉 冊 H u

Now tR is a minimum when k⬘ ⫽ 2, that is, when tR ⫽ 3tM . There is little increase in analysis time when k⬘ lies between 1 and 10. A twofold increase in the mobile-phase velocity roughly halves the analysis time (actually it is the ratio H/u which influences the analysis time). The ratio H/u can be obtained from the experimental plate height/velocity graph. 11.4.2.8 High-Performance Liquid Chromatography. Typical performances for various experimental conditions are given in Table 11.15. The data assume these reduced parameters: h ⫽ 3, v ⫽ 4.5. The reduced plate height is h⫽

H L ⫽ dp Ndp

The reduced velocity of the eluent is v⫽

udp Ldp ⫽ DM tMDM

In these expressions, dp is the particle diameter of the stationary phase that constitutes one plate height. DM is the diffusion coefficient of the solute in the mobile phase.

TABLE 11.15 Typical Performances in HPLC for Various Conditions Performances

Column parameters

N

tM, s

L, cm

d p , ␮m

2 500 2 500 2 500

30 30 30

2.3 3.7 7.5

3 5 10

18.4 (270) 18.4 (270) 18.4 (270)

5 000 5 000 5 000

30 30 30

4.5 7.5 15.0

3 5 10

74 (1088) 74 (1088) 74 (1088)

10 000 10 000 10 000

30 30 30

9.0 15.0 30.0

3 5 10

300 (4410) 300 (4410) 300 (4410)

10 000 10 000 10 000

30 60 90

9.0 9.0 9.0

3 3 3

300 (4410) 150 (2200) 100 (1470)

15 000 15 000

90 120

2.3 2.3

3 3

223 (3275) 167 (2459)

11 100 11 100 11 100

30 37 101

10.0 10.0 10.0

3 3 3

369 (5420) 300 (4410) 100 (1470)

27 800

231

25.0

3

300 (4410)

P, atm (psi)

Assumed reduced parameters: h ⫽ 3 , v ⫽ 4.5. These are optimum values from a graph of reduced plate height versus reduced linear velocity of the mobile phase.

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SECTION 11

Ion-Exchange (Normal Pressure, Columnar)

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Ion-exchange methods are based essentially on a reversible exchange of ions between an external liquid phase and an ionic solid phase. The solid phase consists of a polymeric matrix, insoluble, but permeable, which contains fixed charge groups and mobile counter ions of opposite charge. These counter ions can be exchanged for other ions in the external liquid phase. Enrichment of one or several of the components is obtained if selective exchange forces are operative. The method is limited to substances at least partially in ionized form. 11.4.3.1 Chemical Structure of Ion-Exchange Resins. An ion-exchange resin usually consists of polystyrene copolymerized with divinylbenzene to build up an inert three-dimensional, crosslinked matrix of hydrocarbon chains. Protruding from the polymer chains are the ion-exchange sites distributed statistically throughout the entire resin particle. The ionic sites are balanced by an equivalent number of mobile counter ions. The type and strength of the exchanger is determined by these active groups. Ion-exchangers are designated anionic or cationic, according to whether they have an affinity for negative or positive counter ions. Each main group is further subdivided into strongly or weakly ionized groups. A selection of commercially available ion-exchange resins is given in Table 11.16. The cross-linking of a polystyrene resin is expressed as the proportion by weight percent of divinylbenzene in the reaction mixture; for example, “⫻8” for 8 percent cross-linking. As the percentage is increased, the ionic groups come into effectively closer proximity, resulting in increased selectivity. Intermediate cross-linking, in the range of 4 to 8 percent, is usually used. An increase in cross-linking decreases the diffusion rate in the resin particles; the diffusion rate is the ratecontrolling step in column operations. Decreasing the particle size reduces the time required for attaining equilibrium, but at the same time decreases the flow rate until it is prohibitively slow unless pressure is applied. In most inorganic chromatography, resins of 100 to 200 mesh size are suitable; difficult separations may require 200 to 400 mesh resins. A flow rate of 1 mL · cm⫺2 · min⫺1 is often satisfactory. With HPLC columns, the flow rate in long columns of fine adsorbent can be increased by applying pressure. 11.4.3.1.1 Macroreticular Resins. Macroreticular resins are an agglomerate of randomly packed microspheres which extend through the agglomerate in a continuous non-gel pore structure. The channels throughout the rigid pore structure render the bead centers accessible even in nonaqueous solvents, in which microreticular resins do not swell sufficiently. Because of their high porosity and large pore diameters, these resins can handle large organic molecules. 11.4.3.1.2 Microreticular Resins. Microreticular resins, by contrast, are elastic gels that, in the dry state, avidly absorb water and other polar solvents in which they are immersed. While taking up solvent, the gel structure expands until the retractile stresses of the distended polymer network balance the osmotic effect. In nonpolar solvents, little or no swelling occurs and diffusion is impaired. 11.4.3.1.3 Ion-Exchange Membranes. Ion-exchange membranes are extremely flexible, strong membranes, composed of analytical grade ion-exchange resin beads (90%) permanently enmeshed in a poly(tetrafluoroethylene) membrane (10%). The membranes offer an alternative to column and batch methods, and can be used in many of the same applications as traditional ion exchange resins. Three ion-exchange resin types have been incorporated into membranes: AG 1-X8, AG 50W-X8, and Chelex 100. 11.4.3.2

Functional Groups

Sulfonate exchangers contain the group 9SO⫺3 , which is strongly acidic and completely dissociated whether in the H form or the cation form. These exchangers are used for cation exchange.

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PRACTICAL LABORATORY INFORMATION

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TABLE 11.16 Guide to Ion-Exchange Resins Dowex is the trade name of Dow resins; X (followed by a numeral) is percent cross-linked. Mesh size (dry) are available in the range 50 to 100, 100 to 200, 200 to 400, and sometimes minus 400. S-DVB is the acronym for styrene-divinylbenzene. MP is the acronym for macroporous resin. Mesh size (dry) is available in the range 20 to 50, 100 to 200, and 200 to 400. Bio-Rex is the trade name for certain resins sold by Bio-Rad Laboratories. Amberlite and Duolite are trade names of Rohm & Haas resins. Resin type and nominal percent cross-linkage

Minimum wet capacity, mequiv · mL⫺1

Density (nominal), g · mL⫺1

Comments

Anion exchange resins 9 gel type 9 strongly basic 9 quaternary ammonium functionality Dowex 1-X2

0.6

0.65

Strongly basic anion exchanger with S-DVB matrix for separation of small peptides, nucleotides, and large metal complexes. Molecular weight exclusion is ⬍2700.

Dowex 1-X4

1.0

0.70

Strongly basic anion exchanger with S-DVB matrix for separation of organic acids, nucleotides, phosphoinositides, and other anions. Molecular weight exclusion is ⬍1400.

Dowex 1-X8

1.2

0.75

Strongly basic anion exchanger with S-DVB matrix for separation of inorganic and organic anions with molecular weight exclusion ⬍1000. 100– 200 mesh is standard for analytical separations.

Dowex 2-X8

1.2

0.75

Strongly basic (but less basic than Dowex 1 type) anion exchanger with S-DVB matrix for deionization of carbohydrates and separation of sugars, sugar alcohols, and glycosides.

Amberlite IRA-400

1.4

1.11

8% cross-linkage. Used for systems essentially free of organic materials.

Amberlite IRA-402

1.3

1.07

Lower cross-linkage than IRA-400; better diffusion rate with large organic molecules.

Amberlite IRA-410

1.4

1.12

Dimethylethanolamine functionality and slightly lower basicity than IRA-400.

Amberlite IRA-458

1.2

1.08

Has an acrylic structure rather than S-DVB; hence more hydrophilic and resistant to organic fouling.

Anion exchange resin– gel type 9 intermediate basicity Bio-Rex 5

2.8

0.70

Intermediate basic anion exchanger with primarily tertiary amines on a polyalkyleneamine matrix for separation of organic acids.

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SECTION 11

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TABLE 11.16 Guide to Ion-Exchange Resins (Continued) Resin type and nominal percent cross-linkage

Minimum wet capacity, mequiv · mL⫺1

Density (nominal), g · mL⫺1

Comments

Anion exchange resins 9 gel type 9 weakly basic 9 polyamine functionality Dowex 4-X4

1.6

0.70

Weakly basic anion exchanger with tertiary amines on an acrylic matrix for the deionization of carbohydrates. Use at pH ⬍7.

Amberlite IRA-68

1.6

1.06

Acrylic-DVB with unusually high capacity for large organic molecules.

Cation exchange resins 9 gel type 9 strongly acidic 9 sulfonic acid functionality Dowex 50W-X2

0.6

0.70

Strongly acidic cation exchanger with SDVB matrix for separation of peptides, nucleotides, and cations. Molecular weight exclusion ⬍2700.

Dowex 50W-X4

1.1

0.80

Strongly acidic cation exchanger with SDVB matrix for separation of amino acids, nucleosides and cations. Molecular weight exclusion is ⬍1400.

Dowex 50W-X8

1.7

0.80

Strongly acidic cation exchanger with SDVB matrix for separation of amino acids, metal cations, and cations. Molecular weight exclusion is ⬍1000. 100– 200 mesh is standard for analytical applications.

Dowex 50W-X12

2.1

0.85

Strongly acidic cation exchanger with SDVB matrix used primarily for metal separations.

Dowex 50W-X16

2.4

0.85

Strongly acidic cation exchanger with SDVB matrix and high cross linkage.

Amberlite IR-120

1.9

1.26

8% styrene-DVB type; high physical stability.

Amberlite IR-122

2.1

1.32

10% styrene-DVB type; high physical stability and high capacity.

Weakly acidic cation exchangers 9 gel type 9 carboxylic acid functionality Duolite C-433

4.5

1.19

Acrylic-DVB type; very high capacity. Used for metals removal and neutralization of alkaline solutions.

Bio-Rex 70

2.4

0.70

Weakly acidic cation exchanger with carboxylate groups on a macroreticular acrylic matrix for separation and fractionation of proteins, peptides, enzymes, and amines, particularly high molecular weight solutes. Does not denature proteins as do styrene-based resins.

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PRACTICAL LABORATORY INFORMATION

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TABLE 11.16 Guide to Ion-Exchange Resins (Continued) Resin type and nominal percent cross-linkage

Minimum wet capacity, mequiv · mL⫺1

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Density (nominal), g · mL⫺1

Comments

Selective ion exchange resins Duolite GT-73

1.3

1.30

Removal of Ag, Cd, Cu, Hg, and Pb.

Amberlite IRA743A

0.6

1.05

Boron specific ion exchange resin.

Amberlite IRC-718

1.0

1.14

Removal of transition metals.

Chelex威 100

0.4

0.65

Weakly acidic chelating resin with S-DVB matrix for heavy metal concentration.

Anion exchanger 9 macroreticular type 9 strongly basic 9 quaternary ammonium functionality Amberlite IRA-910

1.1

1.09

Dimethylethanolamine styrene-DVB type which offers slightly less silica removal than Amberlite IRA resin, but offers improved regeneration efficiency.

Amberlite IRA-938

0.5

1.20

Pore size distribution between 2500 and 23 000 nm; suitable for removal of high molecular weight organic materials.

Amberlite IRA-958

0.8

AG MP-1

1.0

Acrylic-DVB; resistant to organic fouling. 0.70

Strongly basic macroporous anion exchanger with S-DVB matrix for separation of some enzymes, radioactive anions, and other applications.

Cation exchange resin 9 macroreticular type 9 sulfonic acid functionality Amberlite 200

1.7

1.26

Styrene-DVB with 20% DVB by weight; superior physical stability and greater resistance to oxidation by factor of three over comparable gel type resin.

AG MP-50

1.5

0.80

Strongly acidic macroporous cation exchanger with S-DVB matrix for separation of radioactive cations and other applications.

Weak cation exchanger 9 macroreticular type 9 carboxylic acid or phenolic functionality Amberlite DP-1

2.5

1.17

Methacrylic acid-DVB; high resin capacity. Use pH ⬎5.

Amberlite IRC-50

3.5

1.25

Methacrylic acid-DVB. Selectivity adsorbs organic gases such as antibiotics, alkaloids, peptides, and amino acids. Use pH ⬎5.

Duolite C-464

3.0

1.13

Polyacrylic resin with high capacity and outstanding resistance to osmotic shock.

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TABLE 11.16 Guide to Ion-Exchange Resins (Continued) Resin type and nominal percent cross-linkage

Minimum wet capacity, mequiv · mL⫺1

Density (nominal), g · mL⫺1

Comments

Weak cation exchanger 9 macroreticular type 9 carboxylic acid or phenolic functionality (continued) Duolite A-7

2.2

1.12

Duolite A-368

1.7

1.04

Amberlite IRA-35

1.1

Amberlite IRA-93

1.3

Phenolic type resin. High porosity and hydrophilic matrix. pH range is 0 to 6. Styrene-DVB; pH range is 0 to 9. Acrylic-DVB; pH range is 0 to 9.

1.04

Styrene-DVB; pH range is 0 to 9. Excellent resistance to oxidation and organic fouling.

Liquid amines Amberlite LA-1

A secondary amine containing two highly branched aliphatic chains of M.W. 351 to 393. Solubility is 15 to 20 mg/mL in water. Used as 5 to 40% solutions in hydrocarbons.

Amberlite LA-2

A secondary amine of M.W. 353 to 395. Insoluble in water. Microcrystalline exchanger

AMP-1

4.0

Microcrystalline ammonium molybdophosphate with cation exchange capacity of 1.2 mequiv/g. Selectively adsorbs larger alkali metal ions from smaller alkali metal ions, particularly cesium. Ion retardation resin

AG 11 A8

0.70

Ion retardation resin containing paired anion (COO⫺) and cation (CH3)3N⫹ sites. Selectively retards ionic substances.

Source: J. A. Dean, ed., Analytical Chemistry Handbook, McGraw-Hill, New York, 1995.

Carboxylate exchangers contain 9COOH groups which have weak acidic properties and will only function as cation exchangers when the pH is sufficiently high (pH ⬎ 6) to permit complete dissociation of the 9COOH site. Outside this range the ion exchanger can be used only at the cost of reduced capacity. Quaternary ammonium exchangers contain 9R4N⫹ groups which are strongly basic and completely dissociated in the OH form and the anion form. Tertiary amine exchangers possess 9 R3NH2 groups which have exchanging properties only in an acidic medium when a proton is bound to the nitrogen atom. Aminodiacetate exchangers have the 9N(CH2COOH)2 group which has an unusually high preference for copper, iron, and other heavy metal cations and, to a lesser extent, for alkaline earth

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cations. The resin selectivity for divalent over monovalent ions is approximately 5000 to 1. The resin functions as a chelating resin at pH 4 and above. At very low pH, the resin acts as an anion exchanger. This exchanger is the column packing often used for ligand exchange.

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11.4.3.3 Ion-Exchange Equilibrium. Retention differences among cations with an anion exchanger, or among anions with a cation exchanger, are governed by the physical properties of the solvated ions. The stationary phase will show these preferences: 1. The ion of higher charge. 2. The ion with the smaller solvated radius. Energy is needed to strip away the solvation shell surrounding ions with large hydrated radii, even though their crystallographic ionic radii may be less than the average pore opening in the resin matrix. 3. The ion that has the greater polarizability (which determines the Van der Waals’ attraction). To accomplish any separation of two cations (or two anions) of the same net charge, the stationary phase must show a preference for one more than the other. No variation in the eluant concentration will improve the separation. However, if the exchange involves ions of different net charges, the separation factor does depend on the eluant concentration. The more dilute the counterion concentration in the eluant, the more selective the exchange becomes for polyvalent ions. In the case of an ionized resin, initially in the H-form and in contact with a solution containing K⫹ ions, an equilibrium exists: resin, H⫹ ⫹ K⫹ N resin, K⫹ ⫹ H⫹ which is characterized by the selectivity coefficient, kK/H: kK/H ⫽

[K⫹]r [H⫹] [H⫹]r [K⫹]

where the subscript r refers to the resin phase. Table 11.17 contains selectivity coefficients for cations and Table 11.18 for anions. Relative selectivities are of limited use for the prediction of the columnar

TABLE 11.17 Relative Selectivity of Various Counter Cations

Counterion

Relative selectivity for AG 50W-X8 resin

H⫹ Li⫹ Na⫹ NH⫹4 K⫹ Rb⫹ Cs⫹ Cu⫹ Ag⫹ Tl⫹ Mn2⫹ Mg2⫹ Fe2⫹

1.0 0.86 1.5 1.95 2.5 2.6 2.7 5.3 7.6 10.7 2.35 2.5 2.55

Counterion

Relative selectivity for AG 50W-X8 resin

Zn2⫹ Co2⫹ Cu2⫹ Cd2⫹ Ni2⫹ Ca2⫹ Sr2⫹ Hg2⫹ Pb2⫹ Ba2⫹ Ce3⫹ La3⫹

2.7 2.8 2.9 2.95 3.0 3.9 4.95 7.2 7.5 8.7 22 22

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TABLE 11.18 Relative Selectivity of Various Counter Anions

Counterion

Relative selectivity for Dowex 1-X8 resin

Relative selectivity for Dowex 2-X8 resin

OH⫺ Benzenesulfonate⫺ Salicylate⫺ Citrate I⫺ Phenate⫺ HSO⫺4 ClO⫺3 NO⫺3 Br⫺ CN⫺ HSO⫺3 BrO⫺3 NO⫺2 Cl⫺ ClO⫺4 SCN⫺ HCO⫺3 IO⫺3 H2PO4⫺ Formate⫺ Acetate⫺ Propanoate⫺ F⫺

1.0 500 450 220 175 110 85 74 65 50 28 27 27 24 22 20 8.0 6.0 5.5 5.0 4.6 3.2 2.6 1.6

1.0 75 65 23 17 27 15 12 8 6 3 3 3 3 2.3

1.2 0.5 0.5 0.5 0.5 0.3 0.3

exchange behavior of a cation because they do not take account of the influence of the aqueous phase. More specific information about the behavior to be expected from a cation in a column elution experiment is given by the equilibrium distribution coefficient Kd. The partitioning of the potassium ion between the resin and solution phases is described by the concentration distribution ratio, Dc: (Dc )K ⫽

[K⫹]r [K⫹]

Combining the equations for the selectivity coefficient and for Dc : (Dc )K ⫽ kK/H

[H⫹]r [H⫹]

The foregoing equation reveals that essentially the concentration distribution ratio for trace concentrations of an exchanging ion is independent of the respective solution of that ion and that the uptake of each trace ion by the resin is directly proportional to its solution concentration. However, the

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concentration distribution ratios are inversely proportional to the solution concentration of the resin counterion. To accomplish any separation of two cations (or two anions), one of these ions must be taken up by the resin in distinct preference to the other. This preference is expressed by the separation factor (or relative retention), ␣K/Na, using K⫹ and Na⫹ as the example:

␣K/Na ⫽

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(Dc )K k ⫽ K/H ⫽ KK/Na (Dc )Na kNa/H

The more ␣ deviates from unity for a given pair of ions, the easier it will be to separate them. If the selectivity coefficient is unfavorable for the separation of two ions of the same charge, no variation in the concentration of H⫹ (the eluant) will improve the separation. The situation is entirely different if the exchange involves ions of different net charges. Now the separation factor does depend on the eluant concentration. For example, the more dilute the counterion concentration in the eluant, the more selective the exchange becomes for the ion of higher charge. In practice, it is more convenient to predict the behavior of an ion, for any chosen set of conditions, by employing a much simpler distribution coefficient, Dg, which is defined as the concentration of a solute in the resin phase divided by its concentration in the liquid phase, or: Dg ⫽

Dg ⫽

concentration of solute, resin phase concentration of solute, liquid phase

% solute within exchanger volume of solution ⫻ % solute within solution mass of exchanger

Dg remains constant over a wide range of resin to liquid ratios. In a relatively short time, by simple equilibration of small known amounts of resin and solution followed by analysis of the phases, the distribution of solutes may be followed under many different sets of experimental conditions. Variables requiring investigation include the capacity and percent cross-linkage of resin, the type of resin itself, the temperature, and the concentration and pH of electrolyte in the equilibrating solution. By comparing the ratio of the distribution coefficients for a pair of ions, a separation factor (or relative retention) is obtained for a specific experimental condition. Instead of using Dg , separation data may be expressed in terms of a volume distribution coefficient Dv , which is defined as the amount of solution in the exchanger per cubic centimeter of resin bed divided by the amount per cubic centimeter in the liquid phase. The relation between Dg and Dv is given by: Dv ⫽ Dg ␳ where ␳ is the bed density of a column expressed in the units of mass of dry resin per cubic centimeter of column. The bed density can be determined by adding a known weight of dry resin to a graduated cylinder containing the eluting solution. After the resin has swelled to its maximum, a direct reading of the settled volume of resin is recorded. Intelligent inspection of the relevant distribution coefficients will show whether a separation is feasible and what the most favorable eluant concentration is likely to be. In the columnar mode, an ion, even if not eluted, may move down the column a considerable distance and with the next eluant may appear in the eluate much earlier than indicated by the coefficient in the first eluant alone. A

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distribution coefficient value of 12 or lower is required to elute an ion completely from a column containing about 10 g of dry resin using 250 to 300 mL of eluant. A larger volume of eluant is required only when exceptionally strong tailing occurs. Ions may be eluted completely by 300 to 400 mL of eluant from a column of 10 g of dry resin at Dg values of around 20. The first traces of an element will appear in the eluate at around 300 mL when its Dg value is about 50 to 60. Example Shaking 50 mL of 0.001 M cesium salt solution with 1.0 g of a strong cation exchanger in the H-form (with a capacity of 3.0 mequiv · g⫺1) removes the following amount of cesium. The selectivity coefficient, kCs/H , is 2.56, thus:

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[Cs⫹]r[H⫹] ⫽ 2.56 [Cs⫹][H⫹]r The maximum amount of cesium which can enter the resin is 50 mL ⫻ 0.001 M ⫽ 0.050 equiv. The minimum value of [H⫹]r ⫽ 3.00 ⫺ 0.05 ⫽ 2.95 mequiv, and the maximum value, assuming complete exchange of cesium ion for hydrogen ion, is 0.001 M. The minimum value of the distribution ratio is: (Dc )Cs ⫽

[Cs⫹]r (2.56)(2.95) ⫽ ⫽ 7550 [Cs⫹] 0.001

Amount of Cs, resin phase (7550)(1.0 g) ⫽ ⫽ 151 Amount of Cs, solution phase 50 mL Thus, at equilibrium the 1.0 g of resin removed is: 100% ⫺ x ⫽ 151 x with all but 0.66% of cesium ions from solution. If the amount of resin were increased to 2.0 g, the amount of cesium remaining in solution would decrease to 0.33%, half the former value. However, if the depleted solution were decanted and placed in contact with 1 g of fresh resin, the amount of cesium remaining in solution would decrease to 0.004%. Two batch equilibrations would effectively remove the cesium from the solution.

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GRAVIMETRIC ANALYSIS

TABLE 11.19 Gravimetric Factors In the following table the elements are arranged in alphabetical order. Example: To convert a given weight of Al2O3 to its equivalent of Al, multiply by the factor at the right, 0.52926; similarly to convert Al to Al2O3 , multiply by the factor at the left, 1.8894. Factor

Factor ALUMINUM Al ⴝ 26.9815

0.74971 0.058728 0.65829 1.8894 1.4165 0.38233 0.41804 0.29800 0.15300 0.10746 0.11246 4.5197 1.3946 0.58196

Al 4 Al4C3 Al 4 Al(C9H6ON)3 (oxinate) Al 4 AlN Al2O3 4 Al Al2O3 4 Al4C3 Al2O3 4 AlCl3 Al2O3 4 AlPO4 Al2O3 4 Al2(SO4 )3 Al2O3 4 Al2(SO4 )3 · 18H2O Al2O3 4 K2SO4 · Al2(SO4 )3 · 24H2O Al2O3 4 (NH4 )2SO4 · Al2(SO4 )3 · 24H2O AlPO4 4 Al CaF2 4 AlF3 P2O5 4 AlPO4

1.3341 17.027 1.5191 0.52926 0.70596 2.6155 2.3921 3.3557 6.5361 9.3055 8.8922 0.22125 0.71704 1.7183

AMMONIUM NH4 ⴝ 18.03858 1.1013 2.0166 0.74424 1.9171 2.6792 1.6198 1.7663 0.81583 1.9654 0.66277 0.68162 0.87553 14.410 13.604 9.4249 0.82244 0.77648 0.26185 0.17499 0.53793 0.21200 0.94412 0.35449 0.21543 0.21277

Ag 4 NH4Br Ag 4 NH4Cl Ag 4 NH4I AgBr 4 NH4Br AgCl 4 NH4Cl AgI 4 NH4I BaSO4 4 (NH4 )2SO4 Br 4 NH4Br Cl 4 NH4 Cl 4 NH4Cl HCl 4 NH4Cl I 4 NH4I MgNH4PO4 · 6H2O 4 NH3 MgNH4PO4 · 6H2O 4 NH4 MgNH4PO4 · 6H2O 4 (NH4)2O N 4 NH3 N 4 NH4 N 4 NH4Cl N 4 NH4NO3 N 4 (NH4 )2O N 4 (NH4 )2SO4 NH3 4 NH4 NH3 4 (NH4 )2CO3 NH3 4 NH4HCO3 NH3 4 NH4NO3

0.90802 0.49590 1.3437 0.52161 0.37323 0.61737 0.56615 1.2257 0.50881 1.5088 1.4671 1.1422 0.069398 0.073506 0.10610 1.2159 1.2879 3.8189 5.7145 1.8590 4.7169 1.0592 2.8210 4.6419 4.6998

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor AMMONIUM (continued) NH4 ⴝ 18.03858

0.65407 0.48596 0.25777 3.1409 2.9654 2.0543 1.5263 2.5020 1.9428 13.032 12.303 4.1490 2.7728 8.5235 6.3328 3.3592 1.3473 3.1710 0.67470 2.0740 5.7275 5.4074 1.8235 1.2187 3.7462 2.7833 1.4764 2.3505 0.60589

NH3 4 (NH4 )2O NH3 4 NH4OH NH3 4 (NH4 )2SO4 NH4Cl 4 NH3 NH4Cl 4 NH4 NH4Cl 4 (NH4 )2O NH4Cl 4 NH4OH NH4OH 4 N NH4OH 4 NH4 (NH4 )2PtCl6 4 NH3 (NH4 )2PtCl6 4 NH4 (NH4 )2PtCl6 4 NH4Cl (NH4 )2PtCl6 4 NH4NO3 (NH4 )2PtCl6 4 (NH4 )2O (NH4 )2PtCl6 4 NH4OH (NH4 )2PtCl6 4 (NH4 )2SO4 (NH4 )2SO4 4 H2SO4 N2O5 4 NH3 N2O5 4 NH4NO3 N2O5 4 (NH4 )2O Pt 4 NH3 Pt 4 NH4 Pt 4 NH4Cl Pt 4 NH4NO3 Pt 4 (NH4 )2O Pt 4 NH4OH Pt 4 (NH4 )2SO4 SO3 4 NH3 SO3 4 (NH4 )2SO4

1.5289 2.0578 3.8794 0.31838 0.33723 0.48677 0.65516 0.39967 0.51472 0.076737 0.081279 0.24102 0.36065 0.11732 0.15791 0.29769 0.74223 0.31536 1.4821 0.48215 0.17460 0.18493 0.54838 0.82058 0.26694 0.35928 0.67733 0.42545 1.6505

ANTIMONY Sb ⴝ 121.760 0.36460 0.83535 0.75271 0.43646 0.90106 0.72184 0.46042 1.2628 1.0549 0.95053 0.90523 0.76147 0.80110 0.50862 1.3950 1.1653 1.0500 1.6584

Sb 4 KSbO · C4H4O6 · 1⁄2 H2O Sb 4 Sb2O4 Sb 4 Sb2O5 Sb2O3 4 KSbO · C4H4O6 · 1⁄2 H2O Sb2O3 4 Sb2O5 Sb2O3 4 Sb2S5 Sb2O4 4 KSbO · C4H4O6 · 1⁄2 H2O Sb2O4 4 Sb Sb2O4 4 Sb2O3 Sb2O4 4 Sb2O5 Sb2O4 4 Sb2S3 Sb2O4 4 Sb2S5 Sb2O5 4 Sb2S5 Sb2S3 4 KSbO · C4H4O6 · 1⁄2 H2O Sb2S3 4 Sb Sb2S3 4 Sb2O3 Sb2S3 4 Sb2O5 Sb2S5 4 Sb

2.7428 1.1971 1.3285 2.2912 1.1098 1.3853 2.1719 0.79188 0.94796 1.0520 1.1047 1.3133 1.2483 1.9661 0.71683 0.85812 0.95234 0.60299

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TABLE 11.19 Gravimetric Factors (Continued) Factor

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Factor ARSENIC As ⴝ 74.9216

1.3203 0.86079 1.5339 1.6420 1.2436 1.0705 0.79324 2.0699 1.5678 1.3495 4.6729 3.5392 3.0465 2.8482 2.5202 2.0719 1.5692 1.3509 1.2629 1.1174 1.2619 2.5397 1.9235 1.6558 1.5480 1.3697

As2O3 4 As As2O3 4 As2O5 As2O5 4 As As2S3 4 As As2S3 4 As2O3 As2S3 4 As2O5 As2S3 4 As2S5 As2S5 4 As As2S5 4 As2O3 As2S5 4 As2O5 BaSO4 4 As BaSO4 4 As2O3 BaSO4 4 As2O6 BaSO4 4 AsO3 BaSO4 4 AsO4 Mg2As2O7 4 As Mg2As2O7 4 As2O3 Mg2As2O7 4 As2O5 Mg2As2O7 4 AsO2 Mg2As2O7 4 AsO4 Mg2As2O7 4 As2S3 MgNH4AsO4 · 1⁄2 H2O 4 As MgNH4AsO4 · 1⁄2 H2O 4 As2O3 MgNH4AsO4 · 1⁄2 H2O 4 As2O5 MgNH4AsO4 · 1⁄2 H2O 4 AsO3 MgNH4AsO4 · 1⁄2 H2O 4 AsO4

0.75738 1.1617 0.65195 0.60903 0.80413 0.93418 1.2606 0.48311 0.63787 0.74103 0.21400 0.28255 0.32825 0.35110 0.39680 0.48265 0.63726 0.74032 0.79186 0.89493 0.79249 0.39374 0.51988 0.60395 0.64600 0.73008

BARIUM Ba ⴝ 137.34 1.4369 0.94766 0.76088 1.2871 1.8446 1.2165 1.2838 1.6521 2.0345 1.5936 1.8222 1.6994 1.1208 0.95546 1.1827 0.89308 1.5221 1.3783 1.3778 0.28701 0.22300

BaCO3 4 Ba BaCO3 4 BaCl2 BaCO3 4 Ba(HCO3 )2 BaCO3 4 BaO BaCrO4 4 Ba BaCrO4 4 BaCl2 BaCrO4 4 BaCO3 BaCrO4 4 BaO BaSiF6 4 Ba BaSiF6 4 BaF2 BaSiF6 4 BaO BaSO4 4 Ba BaSO4 4 BaCl2 BaSO4 4 BaCl2 · 2H2O BaSO4 4 BaCO3 BaSO4 4 Ba(NO3 )2 BaSO4 4 BaO BaSO4 4 BaO2 BaSO4 4 BaS CO2 4 BaO CO2 4 BaCO3

0.69592 1.0552 1.3143 0.77699 0.54214 0.82205 0.77902 0.60530 0.49152 0.62751 0.54878 0.58843 0.89224 1.0466 0.84554 1.1197 0.65698 0.72554 0.72579 3.4842 4.4842

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor BERYLLIUM Be ⴝ 9.0122

8.8678 2.7753 0.31296 0.14119

BeCl2 4 Be BeO 4 Be BeO 4 BeCl2 BeO 4 BeSO4 · 4H2O

0.11277 0.36033 3.1953 7.0825

BISMUTH Bi ⴝ 208.980 0.89699 1.6648 1.4933 0.48030 0.81183 1.2462 0.53689 1.1178 0.90748 1.2301 1.1034

Bi 4 Bi2O3 BiAsO4 4 Bi BiAsO4 4 Bi2O4 Bi2O3 4 Bi(NO3 )3 · 5H2O Bi2O3 4 BiONO3 BiOCl 4 Bi BiOCl 4 Bi(NO3 )3 · 5H2O BiOCl 4 Bi2O3 BiOCl 4 BiONO3 Bi2S3 4 Bi Bi2S3 4 Bi2O3

1.1148 0.60069 0.66968 2.0820 1.2318 0.80244 1.8626 0.89460 1.1019 0.81291 0.90627

BORON B ⴝ 10.81 3.2199 0.81317 0.59193 0.89693 0.56298 0.36510 6.4005 11.646 3.6171 2.0363 1.3206

B2O3 4 B B2O3 4 BO2 B2O3 4 BO3 B2O3 4 B4O7 B2O3 4 H3BO3 B2O3 4 Na2B4O7 · 10H2O B6C 4 C KBF4 4 B KBF4 4 B2O3 KBF4 4 H3BO3 KBF4 4 Na2B4O7 · 10H2O

0.31057 1.2298 1.6894 1.1149 1.7763 2.7389 0.15624 0.085863 0.27647 0.49108 0.75723

BROMINE Br ⴝ 79.90 1.3499 0.84333 1.3331 2.3499 1.4681 2.3206 0.55756 9.9892 1.1858

Ag 4 Br Ag 4 BrO3 Ag 4 HBr AgBr 4 Br AgBr 4 BrO3 AgBr 4 HBr Br 4 AgCl Br 4 O BrO3 4 Ag

0.74079 1.1858 0.75013 0.42555 0.68117 0.43091 1.7935 0.10010 0.84333

CADMIUM Cd ⴝ 112.40 0.61317 0.47545 1.1423

Cd 4 CdCl2 Cd 4 Cd(NO3 )2 CdO 4 Cd

1.6309 2.1033 0.87539

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TABLE 11.19 Gravimetric Factors (Continued) Factor

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Factor CADMIUM (continued) Cd ⴝ 112.40

0.70045 0.54312 1.2852 0.78806 0.61106 1.1251 0.69298 1.8546 1.1372 0.88177 1.6235

CdO 4 CdCl2 CdO 4 Cd(NO3 )2 CdS 4 Cd CdS 4 CdCl2 CdS 4 Cd(NO3 )2 CdS 4 CdO CdS 4 CdSO4 CdSO4 4 Cd CdSO4 4 CdCl2 CdSO4 4 Cd(NO3 )2 CdSO4 4 CdO

1.4276 1.8412 0.77807 1.2689 1.6365 0.88883 1.4430 0.53919 0.87935 1.1341 0.61595

CALCIUM Ca ⴝ 40.08 3.2352 1.7144 1.3556 0.36111 0.51334 0.71471 2.4973 0.90179 0.61742 1.7848 0.73520 0.58134 1.3726 0.50526 0.71825 0.34593 0.75685 0.41192 0.32572 2.5797 1.8437 0.75946 3.3967 1.2266 1.3602 1.7437 2.4276 1.7691 0.63885 1.2644 0.78479 0.43970 0.77989 0.71883 0.71755 12.098

BaSO4 4 CaS BaSO4 4 CaSO4 BaSO4 4 CaSO4 · 2H2O Ca 4 CaCl2 Ca 4 CaF2 Ca 4 CaO CaCO3 4 Ca CaCO3 4 CaCl2 CaCO3 4 Ca(HCO3 )2 CaCO 4 CaO CaCO3 4 CaSO4 CaCO3 4 CaSO4 · 2H2O CaCO3 4 HCl CaO 4 CaCl2 CaO 4 CaF2 CaO 4 Ca(HCO3 )2 CaO 4 Ca(OH)2 CaO 4 CaSO4 CaO 4 CaSO4 · 2H2O Ca3(PO4 )2 4 Ca Ca3(PO4 )2 4 CaO Ca3(PO4 )2 4 CaSO4 CaSO4 4 Ca CaSO4 4 CaCl2 CaSO4 4 CaCO3 CaSO4 4 CaF2 CaSO4 4 CaO Cl 4 Ca Cl 4 CaCl2 Cl 4 CaO CO2 4 CaO CO2 4 CaCO3 Mg2As2O7 4 Ca3(AsO4 )2 MgO 4 CaO Mg2P2O7 4 Ca3(PO4 )2 (NH4 )3PO4 · 12MoO3 4 Ca3(PO4 )2

0.30910 0.58329 0.73766 2.7692 1.9480 1.3992 0.40044 1.1089 1.6196 0.56029 1.3602 1.7202 0.72856 1.9792 1.3923 2.8907 1.3213 2.4276 3.0701 0.38765 0.54239 1.3167 0.29440 0.81526 0.73520 0.57351 0.41192 0.56526 1.5653 0.79089 1.2742 2.2743 1.2822 1.3912 1.3936 0.082657

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor CALCIUM (continued) Ca ⴝ 40.08

0.65824 0.45761 1.4277 0.58809 0.46502 0.80523

N2O5 4 Ca(NO3)2 P2O3 4 Ca3(PO4)2 SO3 4 CaO SO3 4 CaSO4 SO3 4 CaSO4 · 2H2O WO3 4 CaWO4

1.5192 2.1853 0.70044 1.7004 2.1505 1.2419

CARBON C ⴝ 12.011 3.9913 1.6565 4.9541 2.0561 16.431 4.4842 3.2887 3.4842 1.7421 0.19432 0.24120 0.35000 0.47757 0.24885 1.2742 0.63712 0.33936 3.6641 0.43970 0.54297 0.73341 0.13507 0.22695 0.37986 0.49483 0.31843 0.43957 0.46718 0.59564 0.64762 1.4730 0.52193 0.60143 1.0918 0.38286 0.49737 0.62041 0.41523 0.52388 0.71008 0.45802

Ag 4 HCN Ag 4 KCN AgCN 4 HCN AgCN 4 KCN BaCO3 4 C BaCO3 4 CO2 BaCO3 4 CO3 BaO 4 CO2 BaO 4 CO2 , bicarbonate CN 4 AgCN CN 4 Ag SCN 4 AgSCN SCN 4 CuSCN SCN 4 BaSO4 CaO 4 CO2 CaO 4 CO2 , bicarbonate CO2 4 Ba(HCO3 )2 CO2 4 C CO2 4 CaCO3 CO2 4 Ca(HCO3 )2 CO2 4 CO3 CO2 4 Cs2CO3 CO2 4 CsHCO3 CO2 4 FeCO3 CO2 4 Fe(HCO3 )2 CO2 4 K2CO3 CO2 4 KHCO3 CO2 4 K2O CO2 4 Li2CO3 CO2 4 LiHCO3 CO2 4 Li2O CO2 4 MgCO3 CO2 4 Mg(HCO3 )2 CO2 4 MgO CO2 4 MnCO3 CO2 4 Mn(HCO3 )2 CO2 4 MnO CO2 4 Na2CO3 CO2 4 NaHCO3 CO2 4 Na2O CO2 4 (NH4 )2CO3

0.25054 0.60369 0.20185 0.48637 0.060861 0.22301 0.30407 0.28701 0.57402 5.1461 4.1460 2.8572 2.0939 4.0185 0.78479 1.5696 2.9467 0.27291 2.2743 1.8417 1.3635 7.4033 4.4063 2.6326 2.0209 3.1404 2.2749 2.1405 1.6789 1.5441 0.67887 1.9159 1.6627 0.91595 2.6119 2.0106 1.6118 2.4083 1.9088 1.4083 2.1833

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TABLE 11.19 Gravimetric Factors (Continued) Factor

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Factor CARBON (continued) C ⴝ 12.011

0.55669 0.16471 0.19055 0.30043 0.23542 0.29811 0.41984 0.42474

CO2 4 NH4HCO3 CO2 4 PbCO3 CO2 4 Rb2CO3 CO2 4 RbHCO3 CO2 4 Rb2O CO2 4 SrCO3 CO2 4 Sr(HCO3 )2 CO2 4 SrO

1.7963 6.0713 5.2477 3.3286 4.2477 3.3545 2.3818 2.3545

CERIUM Ce ⴝ 140.12 0.36100 0.24746 0.81408 0.85377 0.49302 1.0527 2.1351 0.44345 0.30397 0.42284 0.28984 0.95352 0.57746

Ce 4 Ce(NO3 )4 Ce 4 Ce(NO3 )4 · 2NH4NO3 · H2O Ce 4 CeO2 Ce 4 Ce2O3 Ce 4 Ce2(SO4 )3 Ce2(C2O4 )3 · 3H2O 4 Ce2(SO4 )3 Ce2(C2O4 )3 · 3H2O 4 Ce CeO2 4 Ce(NO3 )4 CeO2 4 Ce(NO3 )4 · 2NH4NO3 · H2O Ce2O3 4 Ce(NO3 )4 Ce2O3 4 Ce(NO3 )4 · 2NH4NO3 · H2O Ce2O3 4 CeO2 Ce2O3 4 Ce2(SO4 )3

2.7701 4.0411 1.2284 1.1713 2.0283 0.94998 0.46835 2.2551 3.2898 2.3650 3.4502 1.0487 1.7317

CESIUM Cs ⴝ 137.905 0.85127 0.26675 0.21058 0.78944 0.57200 0.81585 0.94326 0.83693 0.77876 2.5341 2.0005 2.0675 2.3903 1.3613 1.0747 1.1106 0.28410

AgCl 4 CsCl Cl 4 Cs Cl 4 CsCl Cs 4 CsCl Cs 4 CsClO4 Cs 4 Cs2CO3 Cs 4 Cs2O Cs2O 4 CsCl Cs2O 4 Cs2SO4 Cs2PtCl6 4 Cs Cs2PtCl6 4 CsCl Cs2PtCl6 4 Cs2CO3 Cs2PtCl6 4 Cs2O Cs2SO4 4 Cs Cs2SO4 4 CsCl Cs2SO4 4 Cs2CO3 SO3 4 Cs2O

1.1747 3.7489 4.7488 1.2667 1.7483 1.2257 1.0602 1.1948 1.2841 0.39461 0.49987 0.48369 0.41835 0.73457 0.93050 0.90038 3.5199

CHLORINE Cl ⴝ 35.453 3.0426 2.9585 4.0425

Ag 4 Cl Ag 4 HCl AgCl 4 Cl

0.32866 0.33801 0.24737

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor CHLORINE (continued) Cl ⴝ 35.453

3.9308 3.5728 0.56526 0.97235 0.58227 1.1193 1.4279 0.69391 1.3339 1.7017 1.1029 2.1029 0.19572 0.34288 1.3429 1.2261 0.64846 1.6485 0.50881 1.4671 1.8121 4.5580

AgCl 4 HCl BaCrO4 4 Cl Ca 4 Cl Cl 4 HCl ClO3 4 AgCl ClO3 4 KCl ClO3 4 NaCl ClO4 4 AgCl ClO4 4 KCl ClO4 4 NaCl K 4 Cl KCl 4 Cl Li 4 Cl Mg 4 Cl MgCl2 4 Cl MnO2 4 Cl Na 4 Cl NaCl 4 Cl NH4 4 Cl NH4Cl 4 HCl (NH4 )2SO4 4 HCl PbCrO4 4 Cl

0.25440 0.27990 1.7691 1.0284 1.7174 0.89340 0.70033 1.4411 0.74967 0.58766 0.90668 0.47553 5.1092 2.9165 0.74467 0.81560 1.5421 0.60663 1.9654 0.68162 0.55185 0.21939

CHROMIUM Cr ⴝ 51.996 4.8721 3.3335 2.5335 2.1841 0.70718 7.4935 1.9231 1.4616 0.76000 0.65519 3.7349 1.9421 1.4710 6.2155 4.2527 3.2320 2.7863 0.90217 1.6642 2.1971

BaCrO4 4 Cr BaCrO4 4 Cr2O3 BaCrO4 4 CrO3 BaCrO4 4 CrO4 BaCrO4 4 Cr2(SO4 )3 · 18H2O Cr3C2 4 C CrO3 4 Cr Cr2O3 4 Cr Cr2O3 4 CrO3 Cr2O3 4 CrO4 K2CrO4 4 Cr K2CrO4 4 CrO3 K2Cr2O7 4 CrO3 PbCrO4 4 Cr PbCrO4 4 Cr2O3 PbCrO4 4 CrO3 PbCrO4 4 CrO4 PbCrO4 4 Cr2(SO4 )3 · 18H2O PbCrO4 4 K2CrO4 PbCrO4 4 K2Cr2O7

0.20525 0.29998 0.39472 0.45786 1.4141 0.13345 0.51999 0.68420 1.3158 1.5263 0.26774 0.51490 0.67979 0.16089 0.23515 0.30941 0.35890 1.1084 0.60090 0.45515

COBALT Co ⴝ 58.9332 0.20249 0.78648

Co 4 Co(NO3 )2 · 6H2O Co 4 CoO

4.9385 1.2715

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TABLE 11.19 Gravimetric Factors (Continued) Factor

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Factor COBALT (continued) Co ⴝ 58.9332

0.20965 7.6743 6.0357 1.3620 1.0712 2.4758 1.9471 3.2233 2.5351 2.6299 2.0684 3.7514 7.0656 5.5569

Co 4 CoSO4 · 7H2O K3[Co(NO2 )6 ] 4 Co K3[Co(NO2 )6 ] 4 CoO Co3O4 4 Co Co3O4 4 CoO Co2P2O7 4 Co Co2P2O7 4 CoO CoNH4PO4 · H2O 4 Co CoNH4PO4 · H2O 4 CoO CoSO4 4 Co CoSO4 4 CoO CoSO4 · 7H2O 4 CoO (CoSO4 )2 · (K2SO4 )3 4 Co (CoSO4 )2 · (K2SO4 )3 4 CoO

4.7698 0.13030 0.16568 0.73422 0.93355 0.40391 0.51357 0.31024 0.39447 0.38024 0.48347 0.26657 0.14153 0.17996

COPPER Cu ⴝ 63.544 0.25071 0.79885 0.25449 1.9141 1.5291 0.31856 1.1259 1.2523 1.0004 1.1122 0.31869 0.91872

Cu 4 Cu2C2H3O2 · (AsO2 )3 Cu 4 CuO Cu 4 CuSO4 · 5H2O CuSCN 4 Cu CuSCN 4 CuO CuO 4 CuSO4 · 5H2O Cu2O 4 Cu Cu2S 4 Cu Cu2S 4 CuO Cu2S 4 Cu2O Cu2S 4 CuSO4 · 5H2O Mg2As2O7 4 Cu2C2H3O2(AsO2 )3

3.9887 1.2518 3.9295 0.52245 0.65400 3.1391 0.88817 0.79854 0.99961 0.89908 3.1379 1.0885

ERBIUM Er ⴝ 167.26 1.1435

Er2O3 4 Er

0.87452

FLUORINE F ⴝ 18.9984 1.5936 2.4513 2.3277 1.9392 2.6847 1.9666 1.6256 1.6486 3.5829 2.4024 0.48666 0.51248 1.2641 3.6011

BaSiF6 4 BaF2 BaSiF6 4 F BaSiF6 4 6HF BaSiF6 4 H2SiF6 BaSiF6 4 SiF4 BaSiF6 4 SiF6 CaF2 4 H2SiF6 CaF2 4 SiF6 CaSO4 4 F CaSO4 4 HF F 4 CaF2 HF 4 CaF2 H2SiF6 4 F H2SiF6 4 2HF

0.62751 0.40795 0.42960 0.51568 0.37249 0.50848 0.61516 0.60658 0.27910 0.29391 2.0548 1.9513 0.79109 0.27769

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor FLUORINE (continued) F ⴝ 18.9984

1.2004 1.3844 1.0141 2.0556 1.9520 0.67218 0.41489 1.9325 1.8351 1.5288 1.8957 1.5504 1.9495 1.5013 1.4256 0.49090 0.30300 1.5629 1.4841 1.2364 2.4050 1.2539 2.2101 1.6498 1.5666 1.3052 2.2394 1.3236

H2SiF6 4 6HF H2SiF6 4 SiF4 H2SiF6 4 SiF6 KF · HF 4 2F KF · HF 4 2HF KF · HF 4 2KF KF · HF 4 2(KF · 2H2O) K2SiF6 4 F K2SiF6 4 6HF K2SiF6 4 H2SiF6 K2SiF6 4 2KF K2SiF6 4 SiF6 NH4F 4 F NH4F · HF 4 2F NH4F · HF 4 2HF NH4F · HF 4 2KF NH4F · HF 4 2(KF · 2H2O) (NH4 )2SiF6 4 F (NH4 )2SiF6 4 6HF (NH4 )2SiF6 4 H2SiF6 (NH4 )2SiF6 4 2NH4F (NH4 )2SiF6 4 SiF6 NaF 4 F Na2SiF6 4 F Na2SiF6 4 6HF Na3SiF6 4 H2SiF6 Na2SiF6 4 2NaF Na2SiF6 4 SiF6

0.83308 0.72233 0.98605 0.48647 0.51228 1.4877 2.4103 0.51748 0.54494 0.65412 0.52751 0.64500 0.51295 0.66611 0.70145 2.0371 3.3003 0.63985 0.67381 0.80881 0.41580 0.79753 0.45246 0.60614 0.63831 0.76619 0.44654 0.75550

GALLIUM Ga ⴝ 69.72 1.3442 1.6898

Ga2O3 4 Ga Ga2S3 4 Ga

0.74392 0.59178

GERMANIUM Ge ⴝ 72.59 1.4408 3.6476

GeO2 4 Ge K2GeF6 4 Ge

0.69404 0.27415

GOLD Au ⴝ 196.967 0.64936 0.47826 0.54995

Au 4 AuCl3 Au 4 HAuCl4 · 4H2O Au 4 KAu(CN)4 · H2O

1.5400 2.0909 1.8183

HYDROGEN H ⴝ 1.0079 8.9365 7.9364 0.35607

H2O 4 H O4H HSCN 4 AgSCN

0.11190 0.12600 2.8084

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TABLE 11.19 Gravimetric Factors (Continued) Factor

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Factor HYDROGEN (continued) H ⴝ 1.0079

0.48586 0.25317

HSCN 4 CuSCN HSCN 4 BaSO4

2.0582 3.9499

INDIUM In ⴝ 114.82 1.2090 1.4189

In2O3 4 In In2S3 4 In

0.82711 0.70476

IODINE I ⴝ 126.904 0.84333 0.85004 1.1294 1.8354 1.8500 1.3423 1.2298 1.4066 1.2836 0.41592 0.41921 1.4081 1.4192 1.0297 0.94343 1.0791 0.98472 2.5899 2.6105 1.8941 1.7353 1.9848 1.8112

Ag 4 HI Ag 4 I AgCl 4 I AgI 4 HI AgI 4 I AgI 4 IO3 AgI 4 IO4 AgI 4 I2O5 AgI 4 I2O7 Pd 4 HI Pd 4 I PdI2 4 HI PdI2 4 I PdI2 4 IO3 PdI2 4 IO4 PdI2 4 I2O5 PdI2 4 I2O7 TlI 4 HI TlI 4 I TlI 4 IO3 TlI 4 IO4 TlI 4 I2O5 TlI 4 I2O7

1.1858 1.1764 0.88543 0.54483 0.54053 0.74498 0.81314 0.71091 0.77904 2.4043 2.3854 0.71020 0.70462 0.97113 1.0600 0.92671 1.0155 0.38612 0.38307 0.52797 0.57627 0.50383 0.55211

IRON Fe ⴝ 55.845 2.2598 0.54503 0.61256 0.37986 0.49483 0.31396 0.44061 0.77730 0.69943 0.72359 0.36763 0.20087 0.14242 0.62011

Ag 4 Fe7(CN)18 (Prussian blue) CN 4 Fe7(CN)18 CO2 4 FeO CO2 4 FeCO3 CO2 4 Fe(HCO3 )2 Fe 4 Fe(HCO3 )2 Fe 4 FeCl2 Fe 4 FeO Fe 4 Fe2O3 Fe 4 Fe3O4 Fe 4 FeSO4 Fe 4 FeSO4 · 7H2O Fe 4 FeSO4 · (NH4 )2SO4 · 6H2O FeO 4 FeCO3

0.44252 1.8347 1.6325 2.6326 2.0209 3.1851 2.2696 1.2865 1.4297 1.3820 2.7201 4.9782 7.0217 1.6126

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor IRON (continued) Fe ⴝ 55.845

0.40390 0.89982 0.49223 0.68915 0.44887 0.33422 1.1113 1.0345 0.52941 0.52561 0.28719 0.20361 0.39934 2.7006 2.0992 1.5741 1.2236 1.1010 0.79699 1.1144 0.52704

FeO 4 Fe(HCO3 )2 FeO 4 Fe2O3 Fe2O3 4 FeCl2 Fe2O3 4 FeCO3 Fe2O3 4 Fe(HCO3 )2 Fe2O3 4 Fe(HCO3 )3 Fe2O3 4 FeO Fe2O3 4 Fe3O4 Fe2O3 4 FePO4 Fe2O3 4 FeSO4 Fe2O3 4 FeSO4 · 7H2O Fe2O3 4 FeSO4 · (NH4 )2SO4 · 6H2O Fe2O3 4 Fe2(SO4 )3 FePO4 4 Fe FePO4 4 FeO FeS 4 Fe FeS 4 FeO FeS 4 Fe2O3 Mg2As2O7 4 FeAsO4 SO3 4 FeO SO3 4 FeSO4

2.4759 1.1113 2.0316 1.4511 2.2278 2.9920 0.89982 0.96662 1.8889 1.9026 3.4820 4.9113 2.5041 0.37029 0.47637 0.63527 0.81726 0.90825 1.2547 0.89738 1.8974

LANTHANUM La ⴝ 138.91 1.1728

La2O3 4 La

0.85268

LEAD Pb ⴝ 207.2 0.77541 0.80141 0.85901 0.92831 1.3422 1.2460 1.5598 0.85198 1.2501 1.4480 1.4142 1.0657 0.83529 0.67388 0.93311 1.1544 0.72219 1.1547 1.0720 0.78895 1.2993 1.4636

Pb 4 PbCO3 Pb 4 (PbCO3 )2 · Pb(OH)2 Pb 4 Pb(OH)2 Pb 4 PbO PbCl2 4 Pb PbCl2 4 PbO PbCrO4 4 Pb PbCrO4 4 Pb(C2H3O2 )2 · 3H2O PbCrO4 4 (PbCO3 )2 · Pb(OH)2 PbCrO4 4 PbO PbCrO4 4 Pb3O4 PbCrO4 4 PbSO4 PbO 4 PbCO3 PbO 4 Pb(NO3 )2 PbO 4 PbO2 PbO2 4 Pb PbO2 4 Pb(NO3 )2 PbS 4 Pb PbS 4 PbO PbS 4 PbSO4 PbSO4 4 BaSO4 PbSO4 4 Pb

1.2896 1.2478 1.1641 1.0772 0.74502 0.80255 0.64110 1.1737 0.79997 0.69061 0.70711 0.93833 1.1972 1.4839 1.0717 0.86622 1.3847 0.86600 0.93287 1.2675 0.76966 0.68323

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TABLE 11.19 Gravimetric Factors (Continued) Factor

top of rh base of rh

Factor LEAD (continued) Pb ⴝ 207.2

0.79944 1.1349 1.1730 0.91561 1.3587 1.2678 1.3270

PbSO4 4 Pb(C2H3O2 )2 · 3H2O PbSO4 4 PbCO3 PbSO4 4 (PbCO3 )2 · Pb(OH)2 PbSO4 4 Pb(NO3 )2 PbSO4 4 PbO PbSO4 4 PbO2 PbSO4 4 Pb3O4

1.2509 0.88112 0.85254 1.0922 0.73599 0.78875 0.75358

LITHIUM Li ⴝ 6.941 0.59562 0.64759 1.4729 6.1086 2.8378 5.3228 0.87147 0.54364 2.4730 4.5491 3.7371 2.1525 0.27176 5.5609 0.91047 1.0447 0.56797 2.5837 0.70214 0.60331 7.9153 1.2967 2.6797 0.72823

CO2 4 Li2CO3 CO2 4 LiHCO3 CO2 4 Li2O LiCl 4 Li LiCl 4 Li2O Li2CO3 4 Li Li2CO3 4 LiCl Li2CO3 4 LiHCO3 Li2CO3 4 Li2O LiHCO3 4 Li2O LiF 4 Li Li2O 4 Li Li2O 4 Li2SO4 Li2PO4 4 Li Li3PO4 4 LiCl Li3PO4 4 Li2CO3 Li3PO4 4 LiHCO3 Li3PO4 4 Li2O Li3PO4 4 Li2SO4 Li3PO4 4 Li2SO4 · H2O Li2SO4 4 Li Li2SO4 4 LiCl SO3 4 Li2O SO3 4 Li2SO4

1.6789 1.5442 0.67894 0.16369 0.35239 0.18787 1.1475 1.8395 0.40436 0.21983 0.26759 0.46457 3.6798 0.17983 1.0983 0.95717 1.7607 0.38704 1.4242 1.6575 0.12634 0.77118 0.37317 1.3732

MAGNESIUM Mg ⴝ 24.305 1.9390 0.94693 6.5755 0.86800 0.54691 2.9173 0.74472 0.25533 0.28883 10.4427 0.91261 0.34876 0.52193

BaSO4 4 MgSO4 BaSO4 4 MgSO4 · 7H2O Br 4 Mg Br 4 MgBr2 Br 4 MgBr2 · 6H2O Cl 4 Mg Cl 4 MgCl2 Mg 4 MgCl2 Mg 4 MgCO3 I 4 Mg I 4 MgI2 Cl 4 MgCl2 · 6H2O CO2 4 MgCO3

0.51572 1.0560 0.15208 1.1521 1.8285 0.34278 1.3429 3.9165 3.4683 0.095761 1.09576 2.8673 1.9160

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor MAGNESIUM (continued) Mg ⴝ 24.305

1.0918 0.57616 10.094 6.0879 1.6581 0.47807 0.27544 0.33489 4.5784 1.1687 0.54737 0.40049 1.3198 0.76040 2.7607 0.92452 0.45150 4.9523 1.9864 0.6651 0.38482

CO2 4 MgO MgCO3 4 Mg(HCO3 )2 MgNH4PO4 · 6H2O 4 Mg MgNH4PO4 · 6H2O 4 MgO MgO 4 Mg MgO 4 MgCO3 MgO 4 Mg(HCO3 )2 MgO 4 MgSO4 Mg2P2O7 4 Mg Mg2P2O7 4 MgCl2 Mg2P2O7 4 MgCl2 · 6H2O Mg2P2O7 4 MgCl2 · KCl · 6H2O Mg2P2O7 4 MgCO3 Mg2P2O7 4 Mg(HCO3 )2 Mg2P2O7 4 MgO Mg2P2O7 4 MgSO4 Mg2P2O7 4 MgSO4 · 7H2O MgSO4 4 Mg SO3 4 MgO SO3 4 MgSO4 SO3 4 MgSO4 · 7H2O

0.91595 1.7356 0.099067 0.16426 0.60311 2.0918 3.6305 2.9860 0.21841 0.85562 1.8269 2.4969 0.75770 1.3151 0.36223 1.0816 2.2149 0.20193 0.50343 1.5034 3.0786

MANGANESE Mn ⴝ 54.9380 1.5457 0.38286 0.62041 0.47793 0.77446 0.63193 0.69599 0.76126 1.5395 0.61711 0.40084 0.89868 0.46978 1.3883 0.66351 0.43098 1.0752 0.96625 0.87731 0.50510 2.5831 1.2345 2.0005 1.6324 0.93980 1.5836

BaSO4 4 MnSO4 CO2 4 MnCO3 CO2 4 MnO Mn 4 MnCO3 Mn 4 MnO Mn 4 MnO2 Mn 4 Mn2O3 MnCO3 4 MnSO4 Mn(HCO3 )2 4 MnCO3 MnO 4 MnCO3 MnO 4 Mn(HCO3 )2 MnO 4 Mn2O3 MnO 4 MnSO4 Mn3O4 4 Mn Mn3O4 4 MnCO3 Mn3O4 4 Mn(HCO3 )2 Mn3O4 4 MnO Mn3O4 4 Mn2O3 Mn3O4 4 MnO2 Mn3O4 4 MnSO4 Mn2P2O7 4 Mn Mn2P2O7 4 MnCO3 Mn2P2O7 4 MnO Mn2P2O7 4 MnO2 Mn2P2O7 4 MnSO4 MnS 4 Mn

0.64696 2.6119 1.6118 2.0924 1.2912 1.5825 1.4368 1.3136 0.64955 1.6205 2.4947 1.1127 2.1286 0.72031 1.5071 2.3203 0.93008 1.0349 1.1399 1.9798 0.38713 0.81002 0.49987 0.61261 1.0641 0.63146

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TABLE 11.19 Gravimetric Factors (Continued) Factor

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Factor MANGANESE (continued) Mn ⴝ 54.9380

0.75687 1.2265 0.57617 2.7486 1.1286 0.53021

MnS 4 MnCO3 MnS 4 MnO MnS 4 MnSO4 MnSO4 4 Mn SO3 4 MnO SO3 4 MnSO4

1.3212 0.81535 1.7356 0.36383 0.88603 1.8860

MERCURY Hg ⴝ 200.59 0.73882 0.92613 0.86220 1.1767 0.86939 0.89889 1.1316 1.0898 1.0146 0.98564 0.85691 0.92091 0.88598 0.71673 0.67903 1.1153 1.0741 0.78426

Hg 4 HgCl2 Hg 4 HgO Hg 4 HgS HgCl 4 Hg HgCl 4 HgCl2 HgCl 4 HgNO3 HgCl 4 Hg2O HgCl 4 HgO HgCl 4 HgS HgS 4 HgCl HgS 4 HgCl2 HgS 4 Hg(CN)2 HgS 4 HgNO3 HgS 4 Hg(NO3 )2 HgS 4 Hg(NO3 )2 · H2O HgS 4 Hg2O HgS 4 HgO HgS 4 HgSO4

1.3535 1.0798 1.1598 0.84981 1.1502 1.1125 0.88371 0.91760 0.98564 1.0146 1.1670 1.0859 1.1287 1.3952 1.4727 0.89658 0.93097 1.2751

MOLYBDENUM Mo ⴝ 95.94 8.9876 1.5003 0.73436 2.0026 1.3348 0.98021 1.0863 0.79771 3.8267 2.5506 1.8730

MoC 4 C MoO3 4 Mo MoO3 4 (NH4 )2MoO4 MoS3 4 Mo MoS4 4 MoO3 MoS3 4 (NH4 )2MoO4 (NH4 )3PO4 · 12MoO3 4 MoO3 (NH4 )3PO4 · 12MoO3 4 (NH4 )2MoO4 PbMoO4 4 Mo PbMoO4 4 MoO3 PbMoO4 4 (NH4 )2MoO4

0.11126 0.66653 1.3617 0.49935 0.74918 1.0202 0.92058 1.2536 0.26132 0.39207 0.53390

NEODYMIUM Nd ⴝ 144.24 1.1664

Nd2O3 4 Nd

0.85735

NICKEL Ni ⴝ 58.71 0.20319 0.20188

Ni 4 Ni dimethylglyoxime Ni 4 Ni(NO3 )2 · 6H2O

4.9215 4.9533

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor NICKEL (continued) Ni ⴝ 58.71

0.78585 0.20902 3.8675 0.25690 0.26598 2.6362 0.53220 2.0716 0.55102

Ni 4 NiO Ni 4 NiSO4 · 7H2O Ni dimethylglyoxime 4 NiO NiO 4 Ni(NO3 )2 · 6H2O NiO 4 NiSO4 · 7H2O NiSO4 4 Ni NiSO4 4 Ni(NO3 )2 · 6H2O NiSO4 4 NiO NiSO4 4 NiSO4 · 7H2O

1.2725 4.7842 0.25856 3.8926 3.7597 0.37934 1.8790 0.48271 1.8148

NIOBIUM Nb ⴝ 92.906 7.7351 8.7353 11.065 1.4305

Nb 4 C NbC 4 C Nb2O5 4 2C Nb2O5 4 Nb

0.12928 0.11448 0.090373 0.69904

NITROGEN N ⴝ 14.0067 3.2731 4.0488 1.8722 0.22229 0.30446 0.36855 0.22590 0.25936 6.0680 1.5738 0.47619 0.65222 0.78951 0.48393 0.55561 0.27028 1.2159 0.31536 0.27467 0.84890 0.86270 0.99050 3.8189 3.5221 15.845 4.1096 3.5794 4.7169 1.2234 1.5480 6.9640

AgNO2 4 HNO2 AgNO2 4 N2O3 KNO3 4 N2O5 N 4 HNO3 N 4 NO2 N 4 N2O3 N 4 NO3 N 4 N2O5 NaNO3 4 N NaNO3 4 N2O5 NO 4 HNO3 NO 4 NO2 NO 4 N2O3 NO 4 NO3 NO 4 N2O5 NH3 4 HNO3 NH3 4 N NH3 4 N2O5 NH3 4 NO3 NH4Cl 4 HNO3 NH4Cl 4 NO3 NH4Cl 4 N2O5 NH4Cl 4 N (NH4)2PtCl6 4 HNO3 (NH4)2PtCl6 4 N (NH4)2PtCl6 4 N2O6 (NH4)2PtCl6 4 NO3 (NH4)2SO4 4 N (NH4)2SO4 4 N2O5 Pt 4 HNO3 Pt 4 N

0.30552 0.24698 053412 4.4987 3.2845 2.7134 4.4268 3.8556 0.16480 0.63539 2.1000 1.5332 1.2666 2.0664 1.7998 3.6999 0.82244 3.1710 3.6407 1.1780 1.1591 1.0096 0.26185 0.28393 0.063112 0.24333 0.27938 0.21200 0.81739 0.64599 0.14360

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TABLE 11.19 Gravimetric Factors (Continued) Factor

top of rh base of rh

Factor NITROGEN (continued) N ⴝ 14.0067

1.5732 1.8062 0.63528 2.8579 0.74125

Pt 4 NO3 Pt 4 N2O5 SO3 4 HNO3 SO3 4 N SO3 4 N2O5

0.63566 0.55364 1.5741 0.34990 1.3491

OSMIUM Os ⴝ 190.2 1.3365

OsO4 4 Os

0.74823

PALLADIUM Pd ⴝ 106.4 0.49873 0.46179 3.3854 3.7342 1.8624

Pd 4 PdCl2 · 2H2O Pd 4 Pd(NO3)2 PdI2 4 Pd K2PdCl6 4 Pd K2PdCl6 4 PdCl2 · 2H2O

2.0051 2.1655 0.29538 0.26779 0.53695

PHOSPHORUS P ⴝ 30.9738 13.514 4.4075 5.8980 9.7730 3.1874 4.2653 0.71833 1.2841 1.7183 2.1853 1.5881 2.1251 0.78392 0.31073 0.53229 3.5929 1.1718 1.5681 60.577 19.757 26.438 0.63773 0.49993 0.19816 0.33946 2.2913 58.057 18.935 25.338 11.526

Ag3PO4 4 P Ag3PO4 4 PO4 Ag3PO4 4 P2O5 Ag4P2O7 4 P Ag4P2O7 4 PO4 Ag4P2O7 4 P2O5 Al2O3 4 P2O5 AlPO4 4 PO4 AlPO4 4 P2O5 Ca3(PO4)2 4 P2O5 FePO4 4 PO4 FePO4 4 P2O5 Mg2P2O7 4 Na2HPO4 Mg2P2O7 4 Na2HPO4 · 12H2O Mg2P2O7 4 NaNH4HPO4 · 4H2O Mg2P2O7 4 P Mg2P2O7 4 PO4 Mg2P2O7 4 P2O5 (NH4)3PO4 · 12MoO3 4 P (NH4)3PO4 · 12MoO3 4 PO4 (NH4)3PO4 · 12MoO3 4 P2O5 P2O5 4 Mg2P2O7 P2O5 4 Na2HPO4 P2O5 4 Na2HPO4 · 12H2O P2O5 4 NaNH4HPO4 · 4H2O P2O5 4 P P2O5 · 24MoO3 4 P P2O5 · 24MoO3 4 PO4 P2O5 · 24MoO3 4 P2O5 U2P2O11 4 P

0.073998 0.22689 0.16955 0.10232 0.31374 0.23445 1.3921 0.77877 0.58196 0.45761 0.62970 0.47056 1.2756 3.2182 1.8787 0.27833 0.85340 0.63773 0.016508 0.050616 0.037824 1.5681 2.0003 5.0464 2.9459 0.43644 0.017225 0.052813 0.039466 0.086762

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SECTION 11

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor PHOSPHORUS (continued) P ⴝ 30.9738

3.7590 5.0303

U2P2O11 4 PO4 U2P2O11 4 P2O5

0.26603 0.19880

PLATINUM Pt ⴝ 195.09 0.93839 2.4912 1.4426 1.1383 2.2753 1.3176 1.0885 0.37668 0.57907 0.45691

K2PtCl6 4 H2PtCl6 · 6H2O K2PtCl6 4 Pt K2PtCl6 4 PtCl4 K2PtCl6 4 PtCl4 · 5H2O (NH4)2PtCl6 4 Pt (NH4)2PtCl6 4 PtCl4 (NH4)2PtCl6 4 PtCl6 Pt 4 H2PtCl6 · 6H2O Pt 4 PtCl4 Pt 4 PtCl4 · 5H2O

1.0657 0.40141 0.69320 0.87854 0.43950 0.75897 0.91872 2.6548 1.7269 2.1886

POTASSIUM K ⴝ 39.098 0.90639 1.4469 0.88021 0.77856 1.6565 0.64978 1.5779 1.1244 1.9223 1.1695 1.0344 2.0561 1.4142 1.0971 1.3045 1.7222 1.7140 2.1166 1.3393 2.0436 0.67145 0.41473 0.72315 0.90668 0.47553 0.28929 0.25589 0.75269 0.46718 0.31843 0.76441 0.59299

Ag 4 KBr Ag 4 KCl Ag 4 KClO3 Ag 4 KClO4 Ag 4 KCN Ag 4 Kl AgBr 4 KBr AgBr 4 KBrO3 AgCl 4 KCl AgCl 4 KClO3 AgCl 4 KClO4 AgCN 4 KCN AgI 4 Kl AgI 4 KlO3 BaCrO4 4 K2CrO4 BaCrO4 4 K2Cr2O7 BaSO4 4 KHSO4 BaSO4 4 K2S BaSO4 4 K2SO4 Br 4 K Br 4 KBr CaF2 4 KF · 2H2O CaSO4 4 KF · 2H2O Cl 4 K Cl 4 KCl Cl 4 KClO3 Cl 4 KClO4 Cl 4 K2O CO2 4 K2O CO2 4 K2CO3 I 4 Kl I 4 KlO3

1.1033 0.69116 1.1361 1.2844 0.60369 1.5390 0.63377 0.88939 0.52020 0.85508 0.96672 0.48637 0.70712 0.91153 0.76659 0.58065 0.58342 0.47245 0.74666 0.48933 1.4893 2.4112 1.3828 1.1029 2.1029 3.4567 3.9080 1.3286 2.1405 3.1404 1.3082 1.6864

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TABLE 11.19 Gravimetric Factors (Continued) Factor

top of rh base of rh

Factor POTASSIUM (continued) K ⴝ 39.098

0.31907 0.83016 0.38673 3.0436 2.5267 1.9067 1.0789 0.50685 0.74466 0.73737 1.5829 0.85563 1.6437 3.5433 1.8584 2.9415 4.2456 3.5245 0.38435 0.68159 0.32021 0.47045 0.46584 0.81194 1.1912 6.2146 3.5165 3.2594 2.4271 2.4034 5.1592 2.7888 0.51224 0.48659 1.2609 0.87031 0.63990 1.0238 0.86179 2.2285 1.8499 1.5804 0.60582 0.71164 0.40040 0.49946 0.44132 0.55051 0.13853 0.16844

K 4 KClO3 K 4 K2O K 4 KNO3 KBr 4 K KBr 4 K2O KCl 4 K KCl 4 K2CO3 KCl 4 K2Cr2O7 KCl 4 KHCO3 KCl 4 KNO3 KCl 4 K2O KCl 4 K2SO4 KClO3 4 KCl KClO4 4 K KClO4 4 KCl KClO4 4 K2O Kl 4 K Kl 4 K2O K2O 4 KClO3 K2O 4 K2CO3 K2O 4 K2Cr2O7 K2O 4 KHCO3 K2O 4 KNO3 KOH 4 K2CO3 KOH 4 K2O K2PtCl6 4 K K2PtCl6 4 K2CO3 K2PtCl6 4 KCl K2PtCl6 4 KHCO3 K2PtCl6 4 KNO3 K2PtCl6 4 K2O K2PtCl6 4 K2SO4 K2PtCl6 4 K2SO4 · Al2(SO4)3 · 24H2O K2PtCl6 4 K2SO4 · Cr2(SO4)3 · 24H2O K2SO4 4 K2CO3 K2SO4 4 KHCO3 K2SO4 4 KHSO4 K2SO4 4 KNO2 K2SO4 4 KNO3 K2SO4 4 K K2SO4 4 K2O K2SO4 4 K2S Mg2As2O7 4 K3AsO4 Mg2As2O7 4 K2HAsO4 Mn2O3 4 K2MnO4 Mn2O3 4 KMnO4 MnS 4 K2MnO4 MnS 4 KMnO4 N 4 KNO3 NH3 4 KNO3

3.1341 1.2046 2.5858 0.32856 0.39578 0.52447 0.92690 1.9730 1.3429 1.3562 0.63177 1.1687 0.60836 0.28222 0.53811 0.33996 0.23554 0.28373 2.6018 1.4672 3.1229 2.1256 2.1466 1.2316 0.83946 0.16091 0.28438 0.30680 0.41201 0.41608 0.19383 0.35857 1.9522 2.0551 0.79308 1.1490 1.5627 0.97674 1.1604 0.44875 0.54056 0.63275 1.6506 1.4052 2.4975 2.0022 2.2659 1.8165 7.2185 5.9368

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor POTASSIUM (continued) K ⴝ 39.098

0.29677 0.44656 1.1466 0.53412 2.4946 1.3084 2.0710 0.38943 0.45941

NO 4 KNO3 N2O3 4 KNO2 N2O5 4 K2O N2O5 4 KNO3 Pt 4 K Pt 4 KCl Pt 4 K2O SiO2 4 K2SiO3 SO3 4 K2SO4

3.3697 2.2393 0.87217 1.8722 0.40086 0.76431 0.48287 2.5679 2.1767

PRASEODYMIUM Pr ⴝ 140.908 1.1703

Pr2O3 4 Pr

0.85449

RHODIUM Rh ⴝ 102.905 0.26758 0.49178

Rh 4 Na3RhCl6 Rh 4 RhCl3

3.7372 2.0334

RUBIDIUM Rb ⴝ 85.468 1.6768 1.1852 0.41480 0.29319 0.70683 0.74016 0.91441 0.64023 1.0472 0.90577 2.1636 0.78828 0.77299 0.70015 3.3857 2.3931 2.5060 1.9754 3.0959 1.1561 0.91133

AgCl 4 Rb AgCl 4 RbCl Cl 4 Rb Cl 4 RbCl Rb 4 RbCl Rb 4 Rb2CO3 Rb 4 Rb2O Rb 4 Rb2SO4 RbCl 4 Rb2CO3 RbCl 4 Rb2SO4 RbClO4 4 Rb Rb2CO3 4 RbHCO3 Rb2O 4 RbCl Rb2O 4 Rb2SO4 Rb2PtCl6 4 Rb Rb2PtCl6 4 RbCl Rb2PtCl6 4 Rb2CO3 Rb2PtCl6 4 RbHCO3 Rb2PtCl6 4 Rb2O Rb2SO4 4 Rb2CO3 Rb2SO4 4 RbHCO3

0.59636 0.84371 2.4108 3.4107 1.4148 1.3511 1.0936 1.5620 0.95497 1.1040 0.46220 1.2686 1.2937 1.4283 0.29536 0.41787 0.39905 0.50623 0.32301 0.86498 1.0973

SELENIUM Se ⴝ 78.96 0.61224 0.54466 0.71161 0.62193

Se 4 H2SeO3 Se 4 H2SeO4 Se 4 SeO2 Se 4 SeO3

1.6334 1.8360 1.4053 1.6079

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TABLE 11.19 Gravimetric Factors (Continued) Factor

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Factor SILICON Si ⴝ 28.086

2.6847 4.6504 2.1163 3.6661 3.3384 0.91111 0.76933 2.1393 0.57730 0.78972 0.65250 1.6651 0.62514

BaSiF6 4 SiF4 BaSiF6 4 SiO2 K2SiF6 4 SiF4 K2SiF6 4 SiO2 SiC 4 C SiC 4 CO2 SiO2 4 H2SiO3 SiO2 4 Si SiO2 4 SiF4 SiO2 4 SiO3 SiO2 4 SiO4 SiO2 4 Si2O SiO2 4 Si(OH)4

0.37249 0.21503 0.47249 0.27277 0.29954 1.0976 1.2998 0.46744 1.7322 1.2663 1.5326 0.60057 1.5997

SILVER Ag ⴝ 107.868 0.63501 0.93096 1.7408 1.3286 0.84371 1.2369 1.7935 1.2412 2.1764 1.2935 1.4031 0.74079 0.42555 0.32866 0.24737 1.1764 0.54053

Ag 4 AgNO3 Ag 4 Ag2O AgBr 4 Ag AgCl 4 Ag AgCl 4 AgNO3 AgCl 4 Ag2O AgCl 4 Br AgCN 4 Ag Agl 4 Ag Ag3PO4 4 Ag Ag4P2O7 4 Ag Br 4 Ag Br 4 AgBr Cl 4 Ag Cl 4 AgCl I 4 Ag I 4 Agl

1.5748 1.0742 0.57445 0.75265 1.1852 0.80847 0.55756 0.80566 0.45947 0.77311 0.71269 1.3499 2.3499 3.0426 4.0425 0.85004 1.8500

SODIUM Na ⴝ 22.9898 1.0483 1.8457 0.71966 1.8249 2.4523 1.5663 1.9440 1.6905 2.9906 1.8518 0.92564 1.6432 0.72442

Ag 4 NaBr Ag 4 NaCl Ag 4 Nal AgBr 4 NaBr AgCl 4 NaCl Agl 4 Nal BaSO4 4 NaHSO4 BaSO4 4 NaHSO4 · H2O BaSO4 4 Na2S BaSO4 4 Na2SO3 BaSO4 4 Na2SO3 · 7H2O BaSO4 4 Na2SO4 BaSO4 4 Na2SO4 · 10H2O

0.95393 0.54179 1.3895 0.54798 0.40778 0.63845 0.51440 0.59156 0.33438 0.54002 1.0803 0.60857 1.3804

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor SODIUM (continued) Na ⴝ 22.9898

0.69198 0.36510 3.4758 0.77657 2.5786 0.94956 0.94433 0.92975 0.52910 1.2845 1.5421 0.60663 1.1442 0.41520 0.71008 1.2292 0.64853 5.5198 0.84662 4.0949 2.5029 1.3206 0.91360 0.83497 0.81462 0.67882 0.78392 0.31073 0.53229 0.49897 4.4759 3.3205 65.502 14.635 28.416 25.768 17.926 10.047 37.650 48.594 21.204 66.894 14.946 29.020 26.315 18.307 10.260 38.451 49.626 21.654

B2O3 4 Na2B4O7 B2O3 4 Na2B4O7 · 10H2O Br 4 Na Br 4 NaBr Br 4 Na2O CaCl2 4 NaCl CaCO3 4 Na2CO3 CaF2 4 NaF CaO 4 Na2CO3 CaSO4 4 Na2CO3 Cl 4 Na Cl 4 NaCl Cl 4 Na2O CO2 4 Na2CO3 CO2 4 Na2O H3BO3 4 Na2B4O7 H3BO3 4 Na2B4O7 · 10H2O I 4 Na I 4 Nal I 4 Na2O KBF4 4 Na2B4O7 KBF4 4 Na2B4O7 · 10H2O Mg2As2O7 4 Na2HAsO3 Mg2As2O7 4 Na2HAsO4 MgCl2 4 NaCl Mg2P2O7 4 Na3PO4 Mg2P2O7 4 Na2HPO4 Mg2P2O7 4 NaHPO4 · 12H2O Mg2P2O7 4 NaNH4 · HPO4 · 4H2O Mg2P2O7 4 Na4P2O7 · 10H2O NaBr 4 Na NaBr 4 Na2O NaOAc · Mg(OAc)2 · UO2(OAc)2 · 61⁄2 H2O 4 Na Triple MgOAc 4 NaBr Triple MgOAc 4 Na2CO3 Triple MgOAc 4 NaCl Triple MgOAc 4 NaHCO3 Triple MgOAc 4 Nal Triple MgOAc 4 NaOH Triple MgOAc 4 Na2O Triple MgOAc 4 Na2SO4 NaOAc · Zn(OAc)2 · UO2(OAc)2 · 6H2O 4 Na Triple ZnOAc 4 NaBr Triple ZnOAc 4 Na2CO3 Triple ZnOAc 4 NaCl Triple ZnOAc 4 NaHCO3 Triple ZnOAc 4 Nal Triple ZnOAc 4 NaOH Triple ZnOAc 4 Na2O Triple ZnOAc 4 Na2SO4

1.4451 2.7389 0.28770 1.2877 0.38781 1.0531 1.0590 1.0756 1.8900 0.77854 0.64846 1.6485 0.87410 2.4083 1.4083 0.81357 1.5419 0.18117 1.1812 0.24420 0.39954 0.75724 1.0946 1.1976 1.2276 1.4731 1.2757 3.2182 1.8787 2.0041 0.22342 0.30116 0.015267 0.066331 0.035192 0.038809 0.055785 0.099535 0.026560 0.020579 0.047161 0.014949 0.066909 0.034459 0.038002 0.054624 0.097464 0.026008 0.020151 0.046180

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TABLE 11.19 Gravimetric Factors (Continued) Factor

top of rh base of rh

Factor SODIUM (continued) Na ⴝ 22.9898

2.5421 1.1028 0.69569 0.82337 1.8859 0.82291 0.74267 1.8213 0.85432 2.0950 2.3051 0.63084 1.7101 1.3250 3.6541 2.7108 6.5198 4.8368 1.3480 0.43659 0.36460 0.77480 0.93653 0.37122 3.0892 1.3401 0.49640 2.2917 0.16480 0.20038 0.081461 0.35303 0.63539 1.7427 0.49993 0.19816 0.33946 0.61564 0.50828 0.25407 1.2918 0.56366

NaCl 4 Na NaCl 4 Na2CO3 NaCl 4 NaHCO3 NaCl 4 Na2HPO4 NaCl 4 Na2O NaCl 4 Na2SO4 NaClO3 4 AgCl NaClO3 4 NaCl NaClO4 4 AgCl NaClO4 4 NaCl Na2CO3 4 Na Na2CO3 4 NaHCO3 Na2CO3 4 Na2O Na2CO3 4 NaOH NaHCO3 4 Na NaHCO3 4 Na2O Nal 4 Na Nal 4 Na2O Na2O 4 Na Na2O 4 Na2HPO4 Na2O 4 NaNO3 Na2O 4 NaOH Na4P2O7 4 Na2HPO4 Na4P2O7 4 Na2HPO4 · 12H2O Na2SO4 4 Na Na2SO4 4 Na2CO3 Na2SO4 4 Na2CO3 · 10H2O Na2SO4 4 Na2O N 4 NaNO3 NH3 4 NaNO3 NH3 4 NaNH4HPO4 · 4H2O NO 4 NaNO3 N2O5 4 NaNO3 N2O5 4 Na2O P2O5 4 Na2HPO4 P2O5 4 Na2HPO4 · 12H2O P2O5 4 NaNH4HPO4 · H2O SO2 4 NaHSO3 SO2 4 Na2SO3 SO2 4 Na2SO3 · 7H2O SO2 4 Na2O SO2 4 Na2SO4

0.39337 0.90678 1.4374 1.2145 0.53025 1.2152 1.3465 0.54907 1.1705 0.47732 0.43381 1.5852 0.58476 0.75473 0.27367 0.36889 0.15338 0.20675 0.74186 2.2905 2.7427 1.2907 1.0678 2.6938 0.32371 0.74620 2.0145 0.43635 6.0680 4.9906 12.276 2.8326 1.5738 0.57383 2.0003 5.0464 2.9459 1.6243 1.9674 3.9360 0.77414 1.7741

STRONTIUM Sr ⴝ 87.62 0.29811 0.77265 0.43588 0.41402 1.6849

CO2 4 SrCO8 SO3 4 SrO SO3 4 SrSO4 Sr 4 Sr(NO3 )2 SrCO3 4 Sr

3.3545 1.2942 2.2942 2.4153 0.59351

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor STRONTIUM (continued) Sr ⴝ 87.62

0.93124 0.70424 0.69759 1.1826 0.65363 0.70189 0.49430 0.48963 2.0963 1.1586 1.2442 0.86793 1.7726

SrCO3 4 SrCl2 SrCO3 4 Sr(HCO3 )2 SrCO3 4 Sr(NO3 )2 SrO 4 Sr SrO 4 SrCl2 SrO 4 SrCO3 SrO 4 Sr(HCO3 )2 SrO 4 Sr(NO3 )2 SrSO4 4 Sr SrSO4 4 SrCl2 SrSO4 4 SrCO3 SrSO4 4 Sr(NO3 )2 SrSO4 4 SrO

1.0738 1.4200 1.4335 0.84559 1.5299 1.4247 2.0231 2.0424 0.47703 0.86308 0.80373 1.1522 0.56413

SULFUR S ⴝ 32.06 2.4064 2.5577 3.8906 6.8486 2.8436 2.3797 7.2792 3.6433 2.9152 2.4297 4.2388 4.5054 1.2250 1.6505 1.3473 2.3492

As2S3 4 H2S As2S3 4 S BaSO4 4 FeS2 BaSO4 4 H2S BaSO4 4 H2SO3 BaSO4 4 H2SO4 BaSO4 4 S BaSO4 4 SO2 BaSO4 4 SO3 BaSO4 4 SO4 CdS 4 H2S CdS 4 S H2SO4 4 SO3 (NH4 )2SO4 4 SO3 (NH4 )2SO4 4 H2SO4 SO3 4 H2S

0.41556 0.39097 0.25703 0.14602 0.35166 0.42022 0.13738 0.27448 0.34302 0.41158 0.23591 0.22196 0.81631 0.60589 0.74223 0.42567

TANTALUM Ta ⴝ 180.948 0.81898 0.50515 16.065 1.0664 0.61680 1.0376

Ta 4 Ta2O5 Ta 4 TaCl5 TaC 4 C TaC 4 Ta Ta2O5 4 TaCl5 Ta2O5 4 Ta2O4

1.2210 1.9796 0.062246 0.93776 1.6213 0.96379

TELLURIUM Te ⴝ 127.60 0.65906 0.55565 0.79950 0.72665 1.5645

Te 4 H2TeO4 Te 4 H2TeO4 · 2H2O Te 4 TeO2 Te 4 TeO3 (TeO2 )2SO3 4 Te

1.5173 1.7997 1.2508 1.3762 0.63918

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TABLE 11.19 Gravimetric Factors (Continued) Factor

top of rh base of rh

Factor THALLIUM Tl ⴝ 204.37

0.87198 0.85218 0.61693 0.76724 0.96232 1.2838 1.4750 1.9977 1.7024 1.7420 1.2325 1.5327 1.9225 1.6176 1.2350

Tl 4 Tl2CO3 Tl 4 TlCl Tl 4 Tll Tl 4 TlNO3 Tl 4 Tl2O Tl2CrO4 4 Tl TlHSO4 4 Tl Tl2PtCl6 4 Tl Tl2PtCl6 4 TlCl Tl2PtCl6 4 Tl2CO3 Tl2PtCl6 4 TlI Tl2PtCl6 4 TlNO3 Tl2PtCl6 4 Tl2O Tl2PtCl6 4 Tl2SO4 Tl2SO4 4 Tl

1.1468 1.1735 1.6209 1.3034 1.0391 0.77895 0.67798 0.50057 0.58740 0.57406 0.81139 0.65243 0.52017 0.61821 0.80971

THORIUM Th ⴝ 232.038 1.1379 0.70627 0.44893

ThO2 4 Th ThO2 4 ThCl4 ThO2 4 Th(NO3 )4 · 6H2O

0.87881 1.4159 2.2275

TIN Sn ⴝ 118.69 0.62600 0.52604 0.45562 0.32297 0.88121 0.78764 0.79478 0.66786 0.57846 0.41005 1.1188

Sn 4 SnCl2 Sn 4 SnCl2 · 2H2O Sn 4 SnCl4 Sn 4 SnCl4 · (NH4Cl)2 Sn 4 SnO Sn 4 SnO2 SnO2 4 SnCl2 SnO2 4 SnCl2 · 2H2O SnO2 4 SnCl4 SnO2 4 SnCl4 · (NH4Cl)2 SnO2 4 SnO

1.5974 1.9010 2.1948 3.0962 1.1348 1.2696 1.2582 1.4973 1.7287 2.4387 0.89382

TITANIUM Ti ⴝ 47.867 2.1059 3.0699 2.0660 1.2752 5.0150 3.0057 3.9853 4.9853 1.2509 1.6299 1.6685

K2TiF6 4 F K2TiF6 4 K K2TiF6 4 2KF K2TiF6 4 2(KF · 2H2O) K2TiF6 4 Ti K2TiF6 4 TiO2 Ti 4 C TiC 4 C TiC 4 Ti TiF4 4 F TiO2 4 Ti

0.47485 0.32574 0.48403 0.78421 0.19940 0.33270 0.25092 0.20059 0.79940 0.61354 0.59934

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor TUNGSTEN W ⴝ 183.85

3.9348 1.3099 6.7515 1.1739 4.2684 1.3060 2.0387 2.4751 1.9626 15.307 0.96837 0.93868 31.614 16.307 1.1741 4.1515 1.2611

FeWO4 4 Fe3O4 FeWO4 4 WO3 MgWO4 4 MgO MgWO4 4 WO3 MnWO4 4 MnO MnWO4 4 WO3 PbWO4 4 PbO PbWO4 4 W PbWO4 4 WO3 W4C W 4 W2C W 4 WC W2C 4 C WC 4 C WO2 4 W WO3 4 Fe WO3 4 W

0.25414 0.76344 0.14812 0.85189 0.23428 0.76571 0.49051 0.40403 0.50952 0.065330 1.0327 1.0653 0.031632 0.061324 0.85175 0.24088 0.79297

URANIUM U ⴝ 238.03 1.1344 1.1792 1.0395 0.55901 1.4998 1.3221

UO2 4 U U3O8 4 U U3O8 4 UO2 U3O8 4 UO2(NO3 )2 · 6H2O U2P2O11 4 U U2P2O11 4 UO2

0.88149 0.84800 0.96200 1.7889 0.66675 0.75639

VANADIUM V ⴝ 50.941 5.2413 1.7852 0.79120

VC 4 C V2O5 4 V V2O5 4 VO4

0.19079 0.56017 1.2639

YTTERBIUM Yb ⴝ 173.04 1.1387

Yb2O3 4 Yb

0.87820

ZINC Zn ⴝ 65.38 2.3955 0.81171 0.80338 2.7288 2.1922 0.59707 0.64898 0.28298 2.3304 1.8722 1.4905 1.1974 0.33885

BaSO4 4 ZnS BaSO4 4 ZnSO4 · 7H2O Zn 4 ZnO ZnNH4PO4 4 Zn ZnNH4PO4 4 ZnO ZnO 4 ZnCl2 ZnO 4 ZnCO3 ZnO 4 ZnSO4 · 7H2O Zn2P2O7 4 Zn Zn2P2O7 4 ZnO ZnS 4 Zn ZnS 4 ZnO ZnS 4 ZnSO4 · 7H2O

0.41745 1.2320 1.2447 0.36646 0.45616 1.6748 1.5409 3.5338 0.42911 0.53413 0.67091 0.83512 2.9511

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TABLE 11.19 Gravimetric Factors (Continued) Factor

Factor ZIRCONIUM Zr ⴝ 91.22 K2ZrF6 4 F K2ZrF6 4 2KF K2ZrF6 4 2(KF · 2H2O) K2ZrF6 4 Zr K2ZrF6 4 ZrO2 ZrC 4 C ZrF4 4 F ZrO2 4 Zr ZrO2 4 ZrP2O7

2.4864 2.4390 1.5054 3.1069 2.3000 8.5946 2.2004 1.3508 0.46470

0.40219 0.41001 0.66427 0.32187 0.43478 0.11635 0.45447 0.74030 2.1519

TABLE 11.20 Elements Precipitated by General Analytical Reagents This table includes the more common reagents used in gravimetric determinations. The lists of elements precipitated are not in all cases exhaustive. The usual solvent for a precipitating agent is indicated in parentheses after its name or formula. When the symbol of an element or radical is italicized, the element may be quantitatively determined by the use of the reagent in question. Reagent

Conditions

Ammonia, NH3 (aqueous)

After removal of acid sulfide group.

Ammonium polysulfide, (NH4)2Sx (aqueous) Anthranilic acid, NH2C6H4COOH (aqueous)

After removal of acid sulfide and (NH4)2S groups. 1% aqueous solution (pH 6); Cu separated from others at pH 2.9. (a) Strongly acid medium.

␣-Benzoin oxime, C6H5CHOHC( " NOH)C6H5 (1– 2% alcohol) Benzidine, H2NC6H4C6H4NH2 (alcohol), 0.1M HCl N-Benzoylphenylhydroxylamine, C6H5CO(C6H5)NOH (aqueous)

Cinchonine, C19H21N2OH, 6M HCl Cupferron, C6H5N(NO)ONH4 (aqueous)

1,2-Cyclohexanedionedioxime

(b) Ammoniacal tartrate medium.

Similar to cupferron (q.v.). Cu, Fe(III), and Al complexes can be weighed as such; Ti compound must be ignited to the oxide.

Substances precipitated Al, Au, Be, Co, Cr, Cu, Fe, Ga, In, Ir, La, Nb, Ni, Os, P, Pb, rare earths, Sc, Si, Sn, Ta, Th, Ti, U, V, Y, Zn, Zr Co, Mn, Ni, Si, Tl, V, W, Zn Ag, Cd, Co, Cu, Fe, Hg, Mn, Ni, Pb, Zn (a) Cr(VI), Mo(VI), Nb, Pd(II), Ta(V), V(V), W(VI) (b) Above list Cd, Fe(III), IO⫺3 , PO43⫺, SO42⫺, W(VI) See Cupferron

Ir, Mo, Pt, W Group precipitant for several higher-charged metal ions from strongly acid solution. Precipitate ignited to metal oxide. More water soluble than dimethylglyoxime; less subject to coprecipitation with metal chelate.

Al, Bi, Cu, Fe, Ga, La, Mo, Nb, Pd, rare earths, Sb, Sn, Ta, Th, Ti, Tl, U, V, W, Zr

See Dimethylglyoxime

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TABLE 11.20 Elements Precipitated by General Analytical Reagents (Continued) Reagent

Conditions

Diammonium hydrogen phosphate, (NH4)2HPO4 (aqueous)

(a) Acid medium. (b) Ammoniacal medium containing citrate or tartrate.

Dimethylglyoxime, [CH3C(NOH)]2 (alcohol)

(a) Dilute HCl or H2SO4 medium. (b) Ammoniacal tartrate medium about pH 8. Weighed as such.

Hydrazine, N2H4 (aqueous) Hydrogen sulfide, H2S

4-Hydroxyphenylarsonic acid, C6H4(OH)AsO(OH)2 (aqueous) 8-Hydroxyquinoline (oxine), C9H6NOH, (alcohol)

(a) 0.2– 0.5M H⫹.

(b) Ammoniacal solution after removal of acid sulfide group. Dilute acid solution. (a) HOAc– OAc⫺ buffer.

(b) Ammoniacal solution.

2-Mercaptobenzothiazole, C6H4(SCN)SH (acetic acid solution) Nitron (diphenylenedianilohydrotriazole), C20H16N4 , (5% acetic acid) 1-Nitroso-2-naphthol, C10H6(NO)OH (very dilute alkali) Oxalic acid, H2C2O4, (aqueous) Phenylarsonic acid, C6H5AsO(OH)2 , (aqueous) Phenylthiohydantoic acid, C6H5N " C(NH2)SCH2COOH (aqueous or alcohol) Picrolonic acid, C10H7O5N4H (aqueous) Propylarsonic acid, C3H9AsO(OH)2 (aqueous) Pyridine plus thiocyanate Quinaldic acid, C9B6NCOOH (aqueous) Salicylaldoxime, C7H5(OH)NOH (alcohol) Silver nitrate, AgNO3 (aqueous)

Ammoniacal solution, except for Cu, when a dilute acid solution is used. Dilute H2SO4 medium.

Substances precipitated (a) Bi, Co, Hf, In, Ti, Zn, Zr (b) Au, Ba, Be, Ca, Hg, In, La, Mg, Mn, Pb, rare earths, Sr, Th, U, Zr (a) Au, Pd, Se (b) Ni (and Co, Fe if present in large amounts) Ag, Au, Cu, Hg, Ir, Os, Pd, Pt, Rh, Ru, Se, Te (a) Ag, As, Au, Bi, Cd, Cu, Ge, Hg, In, Ir, Mo, Os, Pb, Pd, Pt, Re, Rh, Ru, Sb, Se, Sn, Te, Tl, V, W, Zn (b) Co, Fe, Ga, In, Mn, Ni, Tl, U, V, Zn Ce, Fe, Sn, Th, Ti, Zr (a) Ag, Al, Bi, Cd, Co, Cr, Cu, Fe, Ga, Hg, In, La, Mn, Mo, Nb, Ni, Pb, Pd, rare earths, Sb, Ta, Th, Ti, V, W, Zn, Zr (b) Same as in (a) except for Ag; in addition, Ba, Be, Ca, Mg, Sn, Sr Ag, Au, Bi, Cd, Cu, Hg, Ir, Pb, Pt, Rh, Tl B, ClO⫺3 , ClO4⫺, NO3⫺, ReO4⫺ , W

Selective for Co; acid solution. Precipitate ignited to Co3O4 .

Ag, Au, B, Co, Cr, Cu, Fe, Mo, Pd, Ti, V, W, Zr

Dilute acid solution.

Ag, Au, Cu, Hg, La, Ni, Pb, rare earths, Sc, Th, U(IV), W, Zr Bi, Ce(IV), Fe, Hf, Mg, Sn, Ta, Th, Ti, U(IV), W, Zr

Selective precipitants for quadrivalent metals in acid solution. Metals weighed as dioxides.

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Bi, Cd, Co, Cu, Fe, Hg, Ni, Pb, Sb Neutral solution. Preferred for W; see Phenylarsonic acid. Dilute acid solution. Dilute acid solution. Dilute acid solution. (a) Dilute HNO3 solution. (b) Acetate buffer, pH 5– 7.

Ca, Mg, Pb, Th

Ag, Cd, Cu, Mn, Ni Ag, Cd, Co, Cu, Fe, Hg, Mo, Ni, Pb, Pd, Pt(II), U, W, Zn Ag, Bi, Cd, Co, Cu, Fe, Hg, Mg, Mn, Ni, Pb, Pd, V, Zn (a) Br⫺, Cl⫺, I⫺, SCN⫺ (b) As(V), CN⫺, OCN⫺, IO⫺3 , Mo(VI), N⫺3 , S 2⫺, V(V)

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TABLE 11.20 Elements Precipitated by General Analytical Reagents (Continued) Reagent

Conditions

Sodium tetraphenylborate, NaB(C6H5)4 (aqueous)

Tannic acid (tannin), C14H10O9 (aqueous)

Tartaric acid, HOOC(CHOH)2COOH (aqueous) Tetraphenylarsonium chloride, (C6H5)4AsCl (aqueous) Thioglycolic-␤-aminonaphthalide, thionalide, C10H7NHCOCH2SH (alcohol)

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Substances precipitated

Specific for K group of alkali metals from dilute HNO3 or HOAc solution (pH 2), or pH 6.5 in presence of EDTA. Acts as negative colloid that is a flocculent for positively charged hydrous oxide sols. Noteworthy for W in acid solution, and for Ta (from Nb in acidic oxalate medium).

Cs, K, NH⫹4 , Rb

Al, Be, Cr, Ga, Ge, Nb, Sb, Sn, Ta, Th, Ti, U, V, W, Zr

Ca, K, Mg, Sc, Sr, Ta

(C6H5)4AsTlCl4 and (C6H5)4AsReO4 weighed as such. (a) Acid solution. (b) Carbonate medium containing tartrate. (c) Carbonate medium containing tartrate and cyanide. (d) Strongly alkaline medium containing tartrate and cyanide.

Re, Tl

(a) Ag, As, Au, Bi, Cu, Hg, Os, Pb, Pd, Rh, Ru, Sb, Sn, Tl (b) Au, Cd, Cu, Hg(II), Tl(I) (c) Au, Bi, Pb, Sb, Sn, Tl (d) Tl

Source: J. A. Dean, ed., Analytical Chemistry Handbook, McGraw-Hill, New York, 1995.

TABLE 11.21 Cleaning Solutions for Fritted Glassware Material

Cleaning solution

Fatty materials

Carbon tetrachloride.

Organic matter

Hot concentrated sulfuric acid plus a few drops of sodium or potassium nitrate solution.

Albumen

Hot aqueous ammonia or hot hydrochloric acid.

Glucose

Hot mixed acid (sulfuric plus nitric acids).

Copper or iron oxides

Hot hydrochloric acid plus potassium chlorate.

Mercury residue

Not nitric acid.

Silver chloride

Aqueous ammonia or sodium thiosulfate.

Aluminous and siliceous residues

A 2% hydrofluoric acid solution followed by concentrated sulfuric acid; rinse immediately with distilled water followed by a few milliliters of acetone. Repeat rinsing until all trace of acid is removed.

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TABLE 11.22 Common Fluxes

Flux Na2CO3

Melting point, ⬚C 851

Na2CO3 plus an oxidizing agent such as KNO3 , KClO3 , or Na2O2

Types of crucible used for fusion

Type of substances decomposed

Pt

For silicates, and silica-containing samples; alumina-containing samples; insoluble phosphates and sulfates

Pt (do not use with Na2O2 ) or Ni

For samples needing an oxidizing agent

NaOH or KOH

320– 380

Au, Ag, Ni

For silicates, silicon carbide, certain minerals

Na2O2

Decomposes

Fe, Ni

For sulfides, acid-insoluble alloys of Fe, Ni, Cr, Mo, W, and Li; Pt alloys; Cr, Sn, Zn minerals

K2S2O7

300

Pt or porcelain

Acid flux for insoluble oxides and oxidecontaining samples

B2O3

577

Pt

For silicates and oxides when alkalis are to be determined

Ni

For decomposing silicates in the determination of alkali element

CaCO3 plus NH4Cl

TABLE 11.23 Membrane Filters Filter pore size, ␮m

Maximum rigid particle to penetrate, ␮m

Filter pore size, ␮m

Maximum rigid particle to penetrate, ␮m

14 10 8 7 5 3 2 1.2 1.0 0.8

17 12 9.4 9.0 6.2 3.9 2.5 1.5 1.1 0.95

0.65 0.60 0.45 0.30 0.22 0.20 0.10 0.05 0.025

0.68 0.65 0.47 0.32 0.24 0.25 0.108 0.053 0.028

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TABLE 11.24 Porosities of Fritted Glassware

Porosity

Nominal maximum pore size, ␮m

Extra coarse

170– 220

Principal uses Filtration of very coarse materials. Gas dispersion, gas washing, and extractor beds. Support of other filter materials.

Coarse

40– 60

Filtration of coarse materials. Gas dispersion, gas washing, gas absorption. Mercury filtration. For extraction apparatus.

Medium

10– 15

Filtration of crystalline precipitates. Removal of “floaters” from distilled water.

4– 5.5

Filtration of fine precipitates. As a mercury valve. In extraction apparatus.

Fine Very fine

2– 2.5

General bacteria filtrations.

Ultra fine

0.9– 1.4

General bacteria filtrations.

TABLE 11.25 Tolerances for Analytical Weights By Alan D. Westland with Fred E. Beamish. This table gives the individual and group tolerances established by the National Bureau of Standards (Washington, D.C.) for classes M, S, S-1, and P weights. Individual tolerances are “acceptance tolerances” for new weights. Group tolerances are defined by the National Bureau of Standards as follows: “The corrections of individual weights shall be such that no combination of weights that is intended to be used in a weighing shall differ from the sum of the nominal values by more than the amount listed under the group tolerances.” For class S-1 weights, two-thirds of the weights in a set must be within one-half of the individual tolerances given below. No group tolerances have been specified for class P weights. See Natl. Bur. Standards Circ. 547, sec. 1 (1954). Class M

Denomination

Individual tolerance, mg

100 g 50 g 30 g 20 g 10 g

0.50 0.25 0.15 0.10 0.050

5 3 2 1

g g g g

0.034 0.034 0.034 0.034

mg mg mg mg

0.0054 0.0054 0.0054 0.0054

50 mg 30 mg 20 mg

0.0054 0.0054 0.0054

500 300 200 100

Class S

Group tolerance, mg

None specified

0.065

0.0105

0.0105

Individual tolerance, mg

Group tolerance, mg

0.25 0.12 0.074 0.074 0.074

None specified

0.054 0.054 0.054 0.054 0.025 0.025 0.025 0.025 0.014 0.014 0.014

0.154

0.105

0.055

0.034

Class S-1, individual tolerance, mg

Class P, individual tolerance, mg

1.0 0.60 0.45 0.35 0.25

2.0 1.2 0.90 0.70 0.50

0.18 0.15 0.13 0.10

0.36 0.14 0.26 0.20

0.080 0.070 0.060 0.050

0.16 0.14 0.12 0.10

0.042 0.038 0.035

0.085 0.076 0.070

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TABLE 11.25 Tolerances for Analytical Weights (Continued) Class M

Denomination

Individual tolerance, mg

10 mg 5 mg 3 mg 2 mg 1 mg 1⁄2 mg

0.0054 0.0054 0.0054 0.0054 0.0054 0.0054

Class S

Group tolerance, mg

0.0105

Individual tolerance, mg 0.014 0.014 0.014 0.014 0.014 0.014

Group tolerance, mg

0.034

Class S-1, individual tolerance, mg

Class P, individual tolerance, mg

0.030 0.028 0.026 0.025 0.025 0.025

0.060 0.055 0.052 0.050 0.050 ...........

TABLE 11.26 Heating Temperatures, Composition of Weighing Forms, and Gravimetric Factors The minimum temperature required for heating a pure precipitate to constant weight is frequently lower than that commonly recommended in gravimetric procedures. However, the higher temperature is very often still to be preferred in order to ensure that contaminating substances are expelled. The thermal stability ranges of various precipitates as deduced from thermograms are also tabulated. Where a stronger ignition is advisable, the safe upper limit can be ascertained. Gravimetric factors are based on the 1993 International Atomic Weights. The factor Ag: 0.7526 given in the first line of the table indicates that the weight of precipitate obtained (AgCl) is to be multiplied by 0.7526 to calculate the corresponding weight of silver.

Element Ag Al

As

Au Ba Be Bi

Br Ca

Thermal stability range, ⬚C 70– 600 ⬎475 ⬎743 102– 220 200– 275

20– 957 780– 1100 ⬍60 ⬎900

379– 961 70– 946 478– 635 838– 1025

Cd

Ce Cl

218– 420 ⬎360 70– 600

Final heating temperature, ⬚C 130– 150 1200 ⬎743 110 105– 110 850 vacuum at 25 1060 780 ⬍60 1000 100 100 800 130– 150 475– 525 950– 1000 air-dried ⬎320 125 500– 600 130– 150

Composition of weighing form AgCl Al2O3 AlPO4 Al(C9H6NO)3 Al2S3 Mg2As2O7 MgNH4AsO4 · 6H2O Au BaSO4 BaCrO4 BeO BiOCl Bi(C12H10NOS)3 BiPO4 AgBr CaCO3 CaO Ca(picrolonate)2 · 8H2O CdSO4 Cd(C10H6NO2)2 CdS CeO2 AgCl

Gravimetric factors Ag: 0.7526 Al: 0.5293 Al: 0.2212; Al2O3 : 0.4180 Al: 0.0587; Al2O3 : 0.1110 As: 0.6090; As2O3 : 0.8041 As: 0.4827; As2O3 : 0.6373 As: 0.2589 Ba: 0.5884; BaO: 0.6570 Ba: 0.5421; BaO: 0.6053 Be: 0.3603 Bi: 0.8024; Bi2O3 : 0.8946 Bi: 0.2387 Bi: 0.6875; Bi2O3 : 0.7665 Br: 0.4256 Ca: 0.4004; CaO: 0.5601 Ca: 0.7147 Ca: 0.05642 Cd: 0.5392; CdO: 0.6159 Cd: 0.2462 Cd: 0.7781; CdO: 0.8888 Ce: 0.8141 Cl: 0.2474

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TABLE 11.26 Heating Temperatures, Composition of Weighing Forms, and Gravimetric Factors (Continued)

Element Co

Thermal stability range, ⬚C 285– 946

Cr Cu ⬍115

F Fe Ga Hg I In Ir K

66– 538 470– 946 408– 946 60– 900 345– 1200 73– 653

Li Mg Mn

88– 300 ⬎946

Mo N (as NO⫺3 ) Na

20– 242 360– 674

Nb Ni Os P

650– 950 79– 172

Pb

160– 415 271– 959

271– 959 Pd Rb Re

45– 171 70– 674

S Sb SCN⫺ Se Si

358– 946

Final heating temperature, ⬚C 750– 850 130 450– 500 120 105– 120 100– 105 105– 115 110– 115 105 130– 140 900 900 105 130– 150 1200 ⬍653 ⬍270 120 200 1050– 1100 155– 160 1000 1000 ⬎505 500– 525 105 125 900 110– 120 800 (in H2) ⬎477 110 500– 600 600 120 600– 800 105 110 ⬍674 130 110 ⬎780 100 130 110– 120 120– 130 ⬎358

Composition of weighing form Co3O4 Co(C10H6NO2)3 · 2H2O CoSO4 PbCrO4 CuSCN Cu(C7H5NO2)2 Cu(C13H11NO2) Cu(C10H6NO2) · H2O Cu(C12H10NOS)2 · H2O PbClF Fe2O3 Ga2O3 Hg(C12H10NOS)2 AgI In2O3 IrO2 KClO4 K2PtCl6 KIO4 KB(C6H5)4 Li2SO4 Mg2P2O7 Mg(C9H6NO)2 Mn3O4 Mn2P2O7 PbMoO4 MoO3 Nitron nitrate NaMg(UO2)3(C2H3O2)9 · 6.5 H2O Nb2O3 Ni(C4H7N2O2)2 Os metal Mg2P2O7 (NH4)3[P(Mo3O10)4] PbSO4 PbMoO4 PbCrO4 PbSO4 Pb(C12H10NOS)2 Pd(C4H7N2O2)2 Rb2PtCl6 (C6H5)4AsReO4 Nitron perrhenate BaSO4 Sb(C12H10NOS)3 AgSCN CuSCN Se metal SiO2

Gravimetric factors Co: 0.7342 Co: 0.09639; CoO: 0.1226 Co: 0.3802 Cr: 0.1609 Cu: 0.5225; CuO: 0.6540 Cu: 0.1891 Cu: 0.2201 Cu: 0.1494 Cu: 0.1237 F: 0.07261 Fe: 0.6994 Ga: 0.7439 Hg: 0.3169 I: 0.5405 In: 0.8271 Ir: 0.8573 K: 0.2822; K2O: 0.3399 K: 0.1609; K2O: 0.1938 K: 0.1700 K: 0.1091 Li: 0.1263; Li2O: 0.2718 Mg: 0.2184; MgO: 0.3622 Mg: 0.07775; MgO: 0.1289 Mn: 0.7203 Mn: 0.3871; MnO: 0.4998 Mo: 0.2613; MoO3 : 0.3291 Mo: 0.6666 N: 0.3732; NO3 : 0.1652 Na: 0.01527; Na 2O: 0.02058 Nb: 0.6990 Ni: 0.2032; NiO: 0.2586 P: 0.2783; PO4 : 0.8536 P: 0.0165; P2O5 : 0.0378 Pb: 0.6832; PbO: 0.7359 Pb: 0.5643; PbO: 0.6078 Pb: 0.6411 Pb: 0.6832; PbO: 0.7359 Pb: 0.3240 Pd: 0.3162 Rb: 0.2954; Rb2O: 0.3230 Re: 0.2939 Re: 0.3306 S: 0.1374; SO3 : 0.3430; SO4 : 0.4116 Sb: 0.1581 SCN: 0.3500 SCN: 0.4775 SeO2 : 1.4052 Si: 0.4675

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TABLE 11.26 Heating Temperatures, Composition of Weighing Forms, and Gravimetric Factors (Continued)

Element

Thermal stability range, ⬚C

Final heating temperature, ⬚C

⬎834

Sn Sr

900 130– 140 100– 300 105 700– 800 900 900 100 1000 700– 800 800– 900 950– 1000 1000 125 ⬎850 1200

100– 300 Te Th

610– 946

Ti Tl(III) U V W Zn

350– 946

581– 946 ⬎674 ⬎1000

Zr

Composition of weighing form SnO2 Sr(NO3)2 SrSO4 Te metal ThO2 ThP2O7 TiO2 Tl(C12H10NOS) U3O8 V2O5 WO3 ZnO Zn2P2O7 Zn(C10H6NO2)2 · H2O ZrP2O7 ZrO2

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Gravimetric factors Sn: 0.7877 Sr: 0.4140 Sr: 0.4770; SrO: 0.5641 Th: 0.8788 Th: 0.5863 Ti: 0.5992 Tl: 0.4860 U: 0.8480; UO2 : 0.9620 V: 0.5602 W: 0.7930 Zn: 0.8034 Zn: 0.4292; ZnO: 0.5342 Zn: 0.1529 Zr: 0.3440; ZrO2 : 0.4647 Zr: 0.7403

Source: J. A. Dean, ed., Analytical Chemistry Handbook, McGraw-Hill, New York, 1995.

11.6 11.6.1

VOLUMETRIC ANALYSIS Acid-Base Titrations in Aqueous Media

TABLE 11.27 Primary Standards for Aqueous Acid-Base Titrations

Standard

Formula weight

Preparation

Basic substances for standardizing acidic solutions (HOCH3)3CNHH2

121.137

HgO

216.59

Na2B4O7 · 10H2O

381.372

Tris(hydroxymethyl)aminomethane is available commercially as a primary standard. Dry at 100– 103⬚C (⬍110⬚C). In titrations with a strong acid the equivalence point is at about pH 4.5– 5. Equivalent weight is the formula weight. [J. H. Fossum, P. C. Markunas, and J. A. Riddick, Anal. Chem., 23:491 (1951).] Dissolve 100 g pure HgCl2 in 1 L H2O, and add with stirring to 650 mL 1.5 M NaOH. Filter and wash with H2O until washings are neutral to phenolphthalein. Dry to constant weight at or below 40⬚C, and store in a dark bottle. To 0.4 g HgO (⬅ 40 mL 0.1N acid) add 10– 15 g KBr plus 20– 25 mL H2O. Stir, excluding CO2 , until solution is complete. Titrate with acid to pH 5– 8. Equivalent weight is one-half formula weight. Recrystallize reagent-grade salt twice from water at temperatures below 55⬚C. Wash the crystals with H2O, twice with ethanol, and twice with diethyl ether. Let stand in a hygrostat oversaturated NaBr · 2H2O or saturated NaCl-sucrose solution. Use methyl red indicator. Equivalent weight is one-half the formula weight.

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TABLE 11.27 Primary Standards for Aqueous Acid-Base Titrations (Continued) Formula weight

Standard

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Preparation

Basic substances for standardizing acidic solutions (continued) Na2CO3

NaCl

105.989

58.45

Heat reagent-grade material for 1 hr at 255– 265⬚C. Cool in an efficient desiccator. Titrate sample with acid to pH 4– 5 (first green tint of bromocresol green), boil the solution to eliminate the carbon dioxide, cool, and again titrate to pH 4– 5. Equivalent weight is one-half the formula weight. Accurately weigh about 6 g NaCl and dissolve in distilled water. Pass the solution through a well-rinsed cation exchange column (Dowex 50W) in the hydrogen form. The equivalent amount of HCl is washed from the column (in 10 column volumes) into a volumetric flask and made up to volume. Equivalent weight is the formula weight.

Acidic substances for standardizing basic solutions C6H5COOH

122.125

o-C6H4(COOK)(COOH)

204.22

KH(IO3)2

389.915

NH2SO3H

97.09

Pure benzoic acid is available from NIST (National Institute for Science and Technology). Dissolve 0.5 g in 20 mL of neutral ethanol (run a blank), excluding CO2 , add 20– 50 mL, and titrate using phenolphthalein as indicator. Potassium hydrogen o-phthalate is available commercially as primary standard, also from NIST. Dry at ⬍135⬚C. Dissolve in water, excluding CO2 , and titrate with phenolphthalein as indicator. For Ba(OH)2 solution, perform the titration at an elevated temperature to prevent precipitation of Ba phthalate. Potassium hydrogen bis(iodate) is available commercially in a primary standard grade. Dry at 110⬚C. Dissolve a weighed amount of the salt in water, excluding CO2 , and titrate to pH 5– 8. [I. M. Kolthoff and L. H. van Berk, J. Am. Chem. Soc., 48:2800 (1926)]. Hydrogen amidosulfate (sulfamic acid) acts as a strong acid. Primary standard grade is available commercially. Since it does undergo slow hydrolysis, an acid end point (pH 4 to 6.5) should be chosen unless fresh reagent is available, then the end point can be in the range pH 4 to 9. [W. F. Wagner, J. A. Wuellner, and C. E. Feiler, Anal. Chem., 24:1491 (1952). M. J. Butler, G. F. Smith, and L. F. Audrieth, Ind. Eng. Chem., Anal. Ed., 10:690 (1938)].

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TABLE 11.28 Titrimetric (Volumetric) Factors Acids The following factors are the equivalent of 1 mL of normal acid. Where the normality of the solution being used is other than normal, multiply the factors given in the table below by the normality of the solution employed. The equivalents of the esters are based on the results of saponification. The indicators methyl orange and phenolphthalein are indicated by the abbreviations MO and pH, respectively. Substance Ammonia Ammonium Ammonium chloride Ammonium hydroxide Ammonium oleate Ammonium oxide Amyl acetate Barium carbonate (MO) Barium hydroxide Barium oxide Bornyl acetate Calcium carbonate (MO) Calcium hydroxide Calcium oleate Calcium oxide Calcium stearate Casein (N 6.38) Ethyl acetate Glue (N 5.60) Hydrochloric acid Magnesium carbonate (MO) Magnesium oxide Menthyl acetate Methyl acetate Nicotine Nitrogen Potassium carbonate (MO) Potassium carbonate, acid (MO) Potassium nitrate Potassium oleate Potassium oxide Potassium stearate Protein (N 5.70) Protein (N 6.25) Sodium acetate Sodium acetate Sodium borate, tetra- (MO) Sodium borate, tetra- (MO) Sodium carbonate (MO) Sodium carbonate (MO) Sodium carbonate (MO) Sodium carbonate, acid (MO) Sodium hydroxide Sodium oleate

Formula

Grams

NH3 NH4 NH4Cl NH4OH C17H33CO2NH4 (NH4)2O CH3CO2C5H11 BaCO3 Ba(OH)2 BaO CH3CO2C10H17 CaCO3 Ca(OH)2 (C17H33CO2)2Ca CaO (C17H35CO2)2Ca .............................. CH3CO2C2H5 .............................. HCl MgCO3 MgO CH3CO2C10H19 CH3CO2CH3 C10H14N2 N K2CO3 KHCO3 KNO3 C17H33CO2K K2O C17K35CO2K .............................. .............................. CH3CO2Na CH3CO2Na · 3H2O Na2B4O7 Na2B4O7 · 10H2O Na2CO3 Na2CO3 · H2O Na2CO3 · 10H2O NaHCO3 NaOH C17H33CO2Na

0.017031 0.018039 0.053492 0.035046 0.29950 0.026038 0.13019 0.09867 0.085677 0.07667 0.19629 0.05004 0.037047 0.30150 0.02804 0.30352 0.089371 0.088107 0.078445 0.036461 0.04216 0.02016 0.19831 0.074080 0.16224 0.014007 0.06911 0.10012 0.10111 0.32057 0.04710 0.32258 0.079846 0.087550 0.082035 0.13608 0.10061 0.19069 0.052994 0.062002 0.14307 0.084007 0.39997 0.30445

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TABLE 11.28 Titrimetric (Volumetric) Factors (Continued) Acids (continued) Substance Sodium oxalate Sodium oxide Sodium phosphate (MO) Sodium phosphate (MO) Sodium phosphate (MO) Sodium phosphate (PH) Sodium silicate Sodium stearate Sodium sulfide (MO)

Formula

Grams

Na2C2O4 Na2O Na2HPO4 Na2PHO4 · 12H2O Na3PO4 Na3PO4 Na2Si4O9 C17H35CO2Na Na2S

0.067000 0.030990 0.14196 0.35814 0.081970 0.16394 0.15111 0.30647 0.039022

Alkali The following factors are the equivalent of the milliliter of normal alkali. Where the normality of the solution being used is other than normal, multiply the factors given in the table below by the normality of the solution employed. The equivalents of the esters are based on the results of saponification. The indicators methyl orange and phenolphthalein are indicated by the abbreviations MO and PH, respectively. Substance Abietic acid (PH) Acetic acid (PH) Acetic anhydride (PH) Aluminum sulfate Amyl acetate Benzoic acid (PH) Borate tetra- (PH) Boric acid (PH) Boric anhydride (PH) Bornyl acetate Butyric acid (PH) Calcium acetate Calcium oleate Calcium stearate Carbon dioxide (PH) Chlorine Citric acid (PH) Ethyl acetate Formaldehyde Formic acid (PH) Glycerol (sap. of acetyl) Hydriodic acid Hydrobromic acid Hydrochloric acid Lactic acid (PH) Lead acetate Maleic acid (PH) Malic acid (PH) Menthol (sap. of acetyl)

Formula HC20H29O2 CH3CO2H (CH3CO)2O Al2(SO4)3 CH3CO2C5H11 C6H5CO2H B4O7 H3BO3 B2O3 CH3CO2C10H17 C3H7CO2H (CH3CO2)2Ca (C17H33CO2)2Ca (C17H35CO2)2Ca CO2 Cl H3C6H5O7 · H2O CH3CO2C2H5 HCHO HCO2H C3H5(OH)3 HI HBr HCl HC3H5O3 (CH3CO2)2Pb · 3H2O (CHCO2H)2 H2C4H4O5 C10H19OH

Grams 0.30246 0.06005 0.051045 0.05702 0.13019 0.12212 0.03881 0.061833 0.03486 0.19629 0.088107 0.079085 0.30150 0.30352 0.022005 0.035453 0.070047 0.088107 0.030026 0.046026 0.030698 0.12791 0.080917 0.036461 0.090079 0.18966 0.058037 0.067045 0.15627

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TABLE 11.28 Titrimetric (Volumetric) Factors (Continued) Alkali (continued) Substance

Formula

Menthyl acetate Methyl acetate Nitrate Nitric acid Nitrogen Nitrogen pentoxide Oleic acid (PH) Oxalic acid (PH) Oxalic acid (PH) Phosphoric acid (MO) Phosphoric acid (PH) Potassium carbonate, acid (MO) Potassium oleate Potassium oxalate, acid (PH) Potassium phthalate, acid (PH) Potassium stearate Sodium benzoate Sodium borate, tetra- (PH) Sodium borate, tetra- (PH) Sodium carbonate, acid (MO) Sodium oleate Sodium salicylate Stearic acid (PH) Succinic acid (PH) Sulfate Sulfur dioxide (PH) Sulfur trioxide Sulfuric acid Sulfurous acid (PH) Tartaric acid (PH) Tartaric acid (PH)

CH3CO2C10H19 CH3CO2CH3 NO3 HNO3 N N2O5 C17H33CO2H (CO2H)2 (CO2H)2 · 2H2O H3PO4 H3PO4 KHCO3 C17K33CO2K KHC2O4 HC8H4O4K C17H35CO2K C6H5CO2Na Na2B4O7 Na2B4O7 · 10H2O NaHCO3 C17H33CO2Na C6H5OCO2Na C17H35CO2H (CH2CO2H)2 SO4 SO2 SO3 H2SO4 H2SO3 H2C4H4O6 H2C4H4O6 · H2O

Grams 0.19831 0.074080 0.062005 0.063013 0.014007 0.054005 0.28247 0.045018 0.063033 0.097995 0.048998 0.10012 0.32056 0.12813 0.20423 0.32258 0.14411 0.050305 0.095343 0.084007 0.30445 0.16011 0.28449 0.059045 0.048031 0.032031 0.040031 0.049039 0.041039 0.075044 0.084052

Iodine The following factors are the equivalent of 1 mL of normal iodine. Where the normality of the solution being used is other than normal, multiply the factors given in the table below by the normality of the solution employed. Substance Acetone Ammonium chromate Antimony Antimony trioxide Arsenic Arsenic pentoxide Arsenic trioxide Arsenite Bleaching powder Bromine Chlorine Chromic oxide

Formula (CH3)2CO (NH4)2CrO4 Sb Sb2O3 As As2O5 As2O3 AsO3 CaOCl2 Br Cl Cr2O3

Grams 0.0096801 0.050690 0.06088 0.07287 0.037461 0.057460 0.049460 0.061460 0.063493 0.079909 0.035453 0.02533

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TABLE 11.28 Titrimetric (Volumetric) Factors (Continued) Iodine (continued) Substance Chromium trioxide Copper Copper oxide Copper sulfate Copper sulfate Ferric iron Ferric oxide Hydrogen sulfide Iodine Lead chromate Lead dioxide Nitrous acid Oxygen Potassium chlorate Potassium chromate Potassium dichromate Potassium nitrite Potassium permanganate Red lead Sodium chromate Sodium dichromate Sodium dichromate Sodium nitrite Sodium sulfide Sodium sulfide Sodium sulfite Sodium sulfite Sodium thiosulfate Sulfur Sulfur dioxide Sulfurous acid Tin

Formula CrO3 Cu CuO CuSO4 CuSO4 · 5H2O Fe3⫹ Fe2O3 H2S I PbCrO4 PbO2 HNO2 O KClO3 K2CrO4 K2Cr2O7 KNO2 KMnO4 Pb3O4 Na2CrO4 Na2Cr2O7 Na2Cr2O7 · 2H2O NaNO2 Na2S Na2S · 9H2O Na2SO3 Na2SO3 · 7H2O Na2S2O3 S SO2 H2SO3 Sn

Grams 0.033331 0.06354 0.07954 0.15960 0.24968 0.05585 0.07985 0.017040 0.126904 0.10773 0.11959 0.023507 0.0079997 0.020426 0.064733 0.049032 0.042554 0.031608 0.34278 0.053991 0.043661 0.049666 0.034498 0.039022 0.12009 0.063021 0.12607 0.15811 0.016032 0.032031 0.041039 0.059345

Potassium dichromate The following factors are the equivalent of 1 mL of normal potassium dichromate. Where the normality of the solution being used is other than normal, multiply the factors given in the table below by the normality of the solution employed. Substance Chromic oxide Chromium trioxide Ferrous iron Ferrous oxide Ferroso-ferric oxide Ferrous sulfate Ferrous sulfate Glycerol Lead chromate Zinc

Formula Cr2O3 CrO3 Fe2⫹ FeO Fe3O4 FeSO4 FeSO4 · 7H2O C3H5(OH)3 PbCrO4 Zn

Grams 0.025332 0.033331 0.055847 0.071846 0.077180 0.15191 0.27802 0.0065782 0.10773 0.032685

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TABLE 11.28 Titrimetric (Volumetric) Factors (Continued) Potassium permanganate The following factors are the equivalent of 1 mL of normal potassium permanganate. Where the normality of the solution being used is other than normal, multiply the factors given in the table below by the normality of the solution employed. Substance Ammonium oxalate Ammonium oxalate Ammonium peroxydisulfate Antimony Barium peroxide Barium peroxide Calcium carbonate Calcium oxide Calcium peroxide Calcium sulfate Calcium sulfate Ferric oxide Ferroso-ferric oxide Ferrous ammonium sulfate Ferrous oxide Ferrous sulfate Ferrous sulfate Formic acid Hydrogen peroxide Iodine Iron Manganese Manganese dioxide Manganous oxide (Volhard) Molybdenum trioxide titration from yellow ppt. after reduction Oxalic acid Oxalic acid Phosphorus titration from yellow ppt. after reduction Phosphorus pentoxide to titration from yellow ppt. after reduction Potassium dichromate Potassium nitrite Potassium persulfate Sodium nitrite Sodium oxalate Sodium persulfate Tin

Formula

Grams

(NH4)2C2O4 (NH4)2C2O4 · H2O (NH4)2S2O8 Sb BaO2 BaO2 · 8H2O CaCO3 CaO CaO2 CaSO4 CaSO4 · 2H2O Fe2O3 Fe3O4 Fe(NH4)2(SO4)2 · 6H2O FeO FeSO4 FeSO4 · 7H2O HCO2H H2O2 I Fe Mn MnO2 MnO MoO3

0.062049 0.071056 0.11410 0.060875 0.084669 0.15673 0.050045 0.02804 0.036039 0.068071 0.086086 0.079846 0.077180 0.39214 0.071846 0.15191 0.27802 0.023013 0.017007 0.126904 0.055847 0.010988 0.043468 0.035469 0.047979

(CO2H)2 (CO2H)2 · 2H2O P

0.045018 0.063033 0.0008604

P2O5

0.0019715

K2Cr2O7 KNO2 K2S2O8 NaNO2 Na2C2O4 Na2S2O8 Sn

0.049032 0.042552 0.13516 0.034498 0.067000 0.11905 0.059345

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TABLE 11.28 Titrimetric (Volumetric) Factors (Continued) Silver nitrate The following factors are the equivalent of 1 mL of normal silver nitrate. Where the normality of the solution being used is other than normal, multiply the factors given in the table below by the normality of the solution employed. Substance Ammonium bromide Ammonium chloride Ammonium iodide Ammonium thiocyanate Barium chloride Barium chloride Bromine Cadmium chloride Cadmium iodide Calcium chloride Chlorine Ferric chloride Ferrous chloride Hydriodic acid Hydrobromic acid Hydrochloric acid Iodine Lithium chloride Lead chloride Magnesium chloride Magnesium chloride Potassium bromide Potassium chloride Potassium iodide Potassium oxide Potassium thiocyanate Silver Silver iodide Silver nitrate Sodium bromide Sodium bromide Sodium chloride Sodium iodide Sodium iodide Sodium oxide Strontium chloride Strontium chloride Zinc chloride

Formula NH4Br NH4Cl NH4I NH4SCN BaCl2 BaCl2 · 2H2O Br CdCl2 CdI2 CaCl2 Cl FeCl3 FeCl2 HI HBr HCl I LiCl PbCl2 MgCl2 MgCl2 · 6H2O KBr KCl KI K2O KSCN Ag AgI AgNO3 NaBr NaBr · 2H2O NaCl NaI NaI · 2H2O Na2O SrCl2 SrCl2 · 6H2O ZnCl2

Grams 0.097948 0.053492 0.14494 0.076120 0.10412 0.12214 0.079909 0.091653 0.18310 0.055493 0.035453 0.054069 0.063377 0.12791 0.080917 0.036461 0.126904 0.042392 0.13905 0.047609 0.10166 0.11901 0.074555 0.16601 0.047102 0.097184 0.10787 0.23477 0.16987 0.10290 0.13893 0.058443 0.14989 0.18592 0.030990 0.079263 0.13331 0.068138

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TABLE 11.28 Titrimetric (Volumetric) Factors (Continued) Sodium thiosulfate The following factors are the equivalent of 1 mL of normal sodium thiosulfate. Where the normality of the solution being used is other than normal, multiply the factors given in the table below by the normality of the solution employed. Substance Acetone Ammonium chromate Antimony Antimony trioxide Bleaching powder Bromine Chlorine Chromic oxide Chromium trioxide Copper Copper oxide Copper sulfate Copper sulfate Iodine Lead chromate Lead dioxide Nitrous acid Potassium chromate Potassium dichromate Red lead Sodium chromate Sodium dichromate Sodium dichromate Sodium nitrite Sodium thiosulfate Sodium thiosulfate Sulfur Sulfur dioxide Tin

11.6.2

Formula (CH3)2CO (NH4)2CrO4 Sb Sb2O3 CaOCl2 Br Cl Cr2O3 CrO3 Cu CuO CuSO4 CuSO4 · 5H2O I PbCrO4 PbO2 HNO2 K2CrO4 K2Cr2O7 Pb3O4 Na2CrO4 Na2Cr2O7 Na2Cr2O7 · 2H2O NaNO2 Na2S2O3 Na2S2O3 · 5H2O S SO2 Sn

Grams 0.0096801 0.050690 0.06088 0.07287 0.063493 0.079909 0.035453 0.02533 0.033331 0.06354 0.07954 0.15960 0.24968 0.126904 0.10773 0.11959 0.023507 0.064733 0.049032 0.34278 0.053991 0.043661 0.049666 0.034498 0.15811 0.24818 0.016032 0.032031 0.059345

Titrimetric (Volumetric) Factors for Acid-Base Titrations

Titrimetric (volumetric) factors for acids and bases are given in Table 11.28. Suitable indicators for acid-base titrations may be found in Tables 8.23 and 8.24. 11.6.3

Standard Volumetric (Titrimetric) Redox Solutions

Alkaline arsenite, 0.1N As(III) to As(V). Dissolve 4.9460 g of primary standard grade As2O3 in 40 mL of 30% NaOH solution. Dilute with 200 mL of water. Acidify the solution with 6N HCl to the acid color of methyl red indicator. Add to this solution 40 g of NaHCO3 and dilute to 1 L. Ceric sulfate, 0.1N Ce(IV) to Ce(III). Dissolve 63.26 g of cerium(IV) ammonium sulfate dihydrate in 500 mL of 2N sulfuric acid. Dilute the solution to 1 L and standardize against the

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alkaline arsenite solution as follows: measure, accurately, 30 to 40 mL of arsenite solution into an Erlenmeyer flask and dilute to 150 mL. Add slowly, to prevent excessive frothing, 20 mL of 4N sulfuric acid, 2 drops of 0.01M osmium tetraoxide solution, and 4 drops of 1,10-phenanthroline iron(II) complex indicator. Titrate with the ceric sulfate solution to a faint blue endpoint. Compute the normality of the ceric solution from the normality of the arsenite solution.

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Iron(II) ammonium sulfate hexahydrate, 0.1N Fe(II) to Fe(III). Dissolve 39.2139 g of FeSO4 · 2(NH4)2 SO4 · 6H2 O in 500 mL of 1N sulfuric acid and dilute to 1 L. If desired, check against standard dichromate or permanganate solution. Iodine, 0.1N (0 to 1⫺). Dissolve 12.690 g of resublimed iodine in 25 mL of a solution containing 15 g of KI which is free from iodate. After all the solid has dissolved, dilute to 1 L. If desired, check against a standard arsenite or standard thiosulfate solution. Potassium bromate, 0.1N (5⫹ to 1⫺). Weigh out 2.7833 g of KBrO3 , dissolve in water, and dilute to 1 L. Potassium dichromate, 0.1N Cr(VI) to Cr(III). Weigh out 4.9030 g of K2Cr2O7 that has been dried at 120⬚C, dissolve in water, and dilute to 1 L. Potassium iodate, 0.1N (5⫹ to 1⫺). Weigh out exactly 3.5667 g of KIO3 (free from iodide), dried at 120⬚C, and dissolve in water containing about 15 g of KI, and dilute to 1 L. Potassium permanganate, 0.1N (7⫹ to 2⫹). Dissolve about 3.3 g in a liter of distilled water. Allow this to stand for 2 or 3 days, then siphon it carefully through clean glass tubes or filter it through a Gooch crucible into the glass container in which it is to be kept, discarding the first 25 mL and allowing the last inch of liquid to remain in the bottle. In this way any dust or reducing substance in the water is oxidized, and the MnO2 formed is removed. Permanganate solutions should never be allowed to come into contact with rubber, filter paper, or any other organic matter, and should be stored away from light. To standardize the KMnO4 , weigh accurately samples of about 0.3 g of primary standard grade Na2C2O4 into Erlenmeyer flasks, add 150 mL of distilled water and 4 mL of concentrated H2SO4 , and heat to 70⬚C and maintain at this temperature throughout the titration with the permanganate solution. The end point is a faint, permanent pink color throughout the solution. Equivalent weight of Na2C2O4 /2 is 67.000 g. Sodium thiosulfate, 0.1N. Weigh 24.818 g of fresh crystals of Na2S2O3 · 5H2O, dissolve in distilled water. Add 0.5 g of Na2CO3 and 0.5 mL of chloroform as preservative. Dilute to 1 L. Equations for the principal methods for the redox determinations of the elements are given in Table 11.29. Volumetric factors in redox titrations for the common titrants are given in Table 11.28. 11.6.4

Indicators for Redox Titrations

A selected list of redox indicators will be found in Table 8.26. A redox indicator should be selected so that its E 0 is approximately equal to the electrode potential at the equivalent point, or so that the color change will occur at an appropriate part of the titration curve. If n is the number of electrons involved in the transition from the reduced to the oxidized form of the indicator, the range in which the color change occurs is approximately given by E 0 ⫾ 0.06/n volt (V) for a two-color indicator whose forms are equally intensely colored. Since hydrogen ions are involved in the redox equilibria of many indicators, it must be recognized that the color change interval of such an indicator will vary with pH. In Table 8.26, E 0 represents the redox potential at which the color change of the indicator would normally be perceived in a solution containing approximately 1M H⫹. For a one-color indicator this is the potential at which the concentration of the colored form is just large enough to impart a visible color to the solution and depends on the total concentration of indicator added to the solution. If it is the reduced form of the indicator that is colorless, the potential at which the first visible color

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appears becomes less positive as the total concentration of indicator increases. For a two-color indicator, the potential at which the middle tint appears is independent of the total indicator concentration, but may differ from the potentiometrically determined formal potential of the indicator in either direction, depending on which of the two forms is more intensely colored. If the reduced form is the more intense color, the middle tint will appear at a potential more positive than the potentiometrically measured formal potential, which is the potential at which the two forms are present at equal concentrations. In addition to those indicators listed in Table 8.26, there are indicators for bromometric and iodometric titrations:

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Specific reagents for titrations with bromine or bromate Methyl orange or methyl red

Use acid-base indicator solutions. Oxidation causes bleaching of indicator to colorless

Bordeaux acid red 17

Dissolve 2 g dye in 1 L water. The red solution is oxidized to pale yellowish green or colorless.

Naphthol blue black

Dissolve 2 g dye in 1 L water. The blue solution is oxidized to pale red.

Specific reagents for iodometric titrations Organic solvents such as CCl4 , CHCl3

Up to 5 mL solvent is usually added per titration. Near the end point the mixture is shaken vigorously after each addition of titrant, and the appearance or disappearance of the I2 color in the organic layer is observed.

Starch

Suspend 5 g of soluble starch in 50 mL of saturated NaCl solution, and stir slowly into 500 mL of boiling saturated NaCl solution. Cool and bottle. Free iodine produces a blueblack color.

TABLE 11.29 Equations for the Redox Determinations of the Elements with Equivalent Weights Al

Al(C9H6NO)3 ⫹ 3 HCl ⫽ AlCl3 ⫹ 3 C9H7NO (8-hydroxyquinoline) 3 C9H7NO ⫹ 6 Br2 ⫽ 3 C9H5Br2NO ⫹ 6 HBr Al/12 ⫽ 2.2485; Al2O3/24 ⫽ 4.2483

As0

As ⫹ 5 Ce(IV) ⫹ 4 H2O ⫽ H3AsO4 ⫹ 5 Ce(III) ⫹ 5 H⫹ As/5 ⫽ 14.9843

As(III)

5 H3AsO3 ⫹ 2 KMnO4 ⫹ 6 HCl ⫽ 5 H3AsO4 ⫹ 2 MnCl2 ⫹ 3 H2O H3AsO3 ⫹ 2 Ce(SO4)2 ⫹ H2O ⫽ H3AsO4 ⫹ Ce2(SO4)3 ⫹ H2SO4 As/2 ⫽ 37.4608; As2O3/4 ⫽ 49.460 3 H3AsO3 ⫹ KBrO3 (⫹ HCl) ⫽ 3 H3AsO4 ⫹ KBr H3AsO3 ⫹ I2 ⫹ 2 H2O ⫽ H3AsO4 ⫹ 2 I⫺ ⫹ 2 H⫹ As/2 ⫽ 37.4608; As2O3/4 ⫽ 49.460

As(V)

H3AsO4 ⫹ 2 KI (excess) ⫹ 2 HCl ⫽ H3AsO3 ⫹ I2 ⫹ 2 KCl ⫹ H2O I2 ⫹ 2 Na2S2O3 ⫽ 2 NaI ⫹ Na2S4O6 As/2 ⫽ 37.4608; As2O3/4 ⫽ 49.460

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TABLE 11.29 Equations for the Redox Determinations of the Elements with Equivalent Weights (Continued)

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BaCrO4 ⫹ 6 KI (excess) ⫹ 16 HCl ⫽ 2 BaCl2 ⫹ 3 I2 ⫹ 6 KCl ⫹ 2 CrCl3 ⫹ 8 H2O I2 ⫹ 2 Na2S2O3 ⫽ 2 NaI ⫹ Na2S4O6 Ba/3 ⫽ 45.78

Ba

BaCrO4 ⫹ 3 Fe2⫹ (excess) ⫹ 8 H⫹ ⫽ Ba2⫹ ⫹ Cr3⫹ ⫹ 3 Fe3⫹ ⫹ 4 H2O Titrate excess Fe2⫹ with permanganate or dichromate; Ba/3 ⫽ 45.78 Br2

Br2 ⫹ 2 KI (excess) ⫽ 2 KBr ⫹ I2 I2 ⫹ 2 Na2S2O3 : 2 NaI ⫽ Na2S4O6

Br⫺

Br⫺ ⫹ 3 HClO ⫽ BrO⫺3 ⫹ 3 Cl⫺ ⫹ 3 H⫹ Br/6 ⫽ 13.317

BrO⫺3

BrO⫺3 ⫹ 6 I⫺ (excess) ⫹ 6 H⫹ ⫽ Br⫺ ⫹ 3 I2 ⫹ 3H2O I2 ⫹ 2 Na2S2O3 ⫽ 2 NaI ⫹ Na2S4O6 KBrO3/6 ⫽ 27.835

CO

5 CO ⫹ I2O5 ⫽ 5 CO2 ⫹ I2 (at 125⬚C; adsorbed and measured colorimetrically) 5/2 CO ⫽ 70.02

C2O24⫺

Titrate as for CaC2O4

C2O62⫺

Acidify and titrate as for H2O2 ; C2O62⫺ ⫹ 2 H⫹ ⫽ H2O2 ⫹ CO2 K2C2O6/2 ⫽ 99.11

Ca

5 CaC2O4 ⫹ 2 KMnO4 ⫹ 8 H2SO4 ⫽ 5 CaSO4 ⫹ 10 CO2 ⫹ K2SO4 ⫹ 2 MnSO4 ⫹ 8 H2O Ca/2 ⫽ 20.039; CaO/2 ⫽ 28.04

Cd

Cd(anthranilate)2 ⫹ 4 Br2 ⫽ 2 NH2C6H2Br2COOH ⫹ 4 Br⫺ Titrate with KBrO3 9 KBr until color of indigo changes to yellow. Add KI and back-titrate iodine liberated with thiosulfate. Cd/8 ⫽ 14.05

Ce

Oxidize Ce(III) to Ce(IV) with (NH4)2S2O8 plus Ag⫹; destroy excess by boiling. 2 Ce(SO4)2 ⫹ 2 FeSO4 ⫽ Ce2(SO4)3 ⫹ Fe2(SO4)3 Ce/1 ⫽ 140.12; Ce2O3/2 ⫽ 164.12

Br2/2 ⫽ 79.904

Same as for Br2 ; Cl2/2 ⫽ 35.453

Cl2 ⫺

ClO

ClO⫺ ⫹ 2 I⫺ ⫹ 2 H ⫽ Cl⫺ ⫹ I2 ⫹ H2O Titrate liberated I2 with thiosulfate; HClO/2 ⫽ 26.230

ClO⫺2

ClO⫺2 ⫹ 4 I⫺ ⫹ 4 H⫹ ⫽ Cl⫺ ⫹ 2 I2 ⫹ 2 H2O Titrate liberated I2 with thiosulfate; HClO/2 ⫽ 26.230

ClO⫺3

ClO⫺3 ⫹ 6 I⫺ ⫹ 6 H2O ⫽ Cl⫺ ⫹ 3 I2 ⫹ 3 H2O Titrated liberated I2 with thiosulfate; HClO2/4 ⫽ 17.115 ClO⫺3 ⫹ 3 H3AsO3 (excess; boil with strong HCl) ⫽ Cl⫺ ⫹ 3 H3AsO4 Titrate excess H3AsO3 with bromate; HClO3/6 ⫽ 14.077

Co

Co(NH3)62⫹ ⫹ Fe(CN)63 ⫺ [Citrate-NH3 buffer] ⫽ Co(NH3 )63⫹ ⫹ Fe(CN)64 ⫺ Co/1 ⫽ 58.9332 Precipitate Co anthranilate and treat as for cadmium; Co/8 ⫽ 7.3667

Cr

Cr2O27 ⫺ ⫹ 6 Fe2⫹ ⫹ 14 H⫹ ⫽ 2 Cr3⫹ ⫹ 6 Fe3⫹ ⫹ 7 H2O Cr/3 ⫽ 17.332; Cr2O3/6 ⫽ 25.337

Cu

2 Cu2⫹ ⫹ 2 I⫺ ⫹ 2SCN⫺ ⫽ 2CuSCN ⫹ I2 Titrate the liberated iodine with thiosulfate; Cu/1 ⫽ 63.546 4 CuSCN ⫹ 7 IO3 ⫺ ⫹ 14 H⫹ ⫹ 7 Cl ⫺ ⫽ 4 Cu2⫹ ⫹ 4 SO24 ⫺ ⫹ 7 ICl ⫹ 4 HCN ⫹ 5 H2O Precipitate and wash CuSCN. Titrate with standard KIO3 solution with 5 mL CHCl3 until a definite I2 color appears in the organic layer. Back-titrate the excess I2 with standard thiosulfate solution. Cu/7 ⫽ 9.078; KIO3/4 ⫽ 53.505

Fe(II)

5 Fe2⫹ ⫹ MnO4⫺ ⫹ 8 H⫹ ⫽ 5 Fe3⫹ ⫹ Mn2⫹ ⫹ 4 H2O Fe2⫹ ⫹ Ce(IV) ⫽ Fe3⫹ ⫹ Ce(III); use 1,10-phenanthroline iron(II) indicator. 6 Fe2⫹ ⫹ Cr2O72 ⫺ ⫹ 14 H⫹ ⫽ 6 Fe3⫹ ⫹ 2 Cr3⫹ ⫹ 7 H2O; use diphenylamine sulfonate indicator. Fe/1 ⫽ 55.847; Fe2O3/2 ⫽ 79.845

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TABLE 11.29 Equations for the Redox Determinations of the Elements with Equivalent Weights (Continued) Fe(III)

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Fe3⫹ ⫹ 4 SCN ⫺ ⫽ Fe(SCN)4⫺ ; Fe(SCN)4⫺ ⫹ Ti(III) ⫽ Fe2⫹ ⫹ Ti(IV) ⫹ 4 SCN ⫺ Fe/1 ⫽ 55.847; Fe2O3/2 ⫽ 79.845 2 Fe3⫹ ⫹ Zn ⫽ 2 Fe2⫹ ⫹ Zn2⫹; then proceed by a method under Fe(II). Fe3⫹ ⫹ Ag ⫹ Cl ⫺ ⫽ Fe2⫹ ⫹ AgCl; then proceed by a method under Fe(II). 2 Fe3⫹ ⫹ SnCl2(slight excess) ⫹ 4 Cl ⫺ ⫽ 2 Fe2⫹ ⫹ SnCl26 ⫺ 2 HgCl2 ⫹ SnCl2 ⫹ 2 Cl⫺ ⫽ Hg2Cl2 ⫹ SnCl26 ⫺ Pour above mixture into an H3PO4 plus MnSO4 solution and titrate with KMnO4 as under Fe(II). Fe/1 ⫽ 55.847; Fe2O3/2 ⫽ 79.845 2 Fe3⫹ ⫹ 2 I ⫺ ⫽ Fe2⫹ ⫹ I2 Titrate liberated iodine with thiosulfate; Fe/1 ⫽ 55.847; Fe2O3/2 ⫽ 79.845

I2

I2 ⫹ 2 S2O23⫺ ⫽ 2 I ⫺ ⫹ S4O62 ⫺ [titrate solution (pH ⴰ 7.0) with thiosulfate until color is pale yellow. Add KI and starch and continue titration to disappearance of blue color. I2/2 ⫽ 126.9045 I2 ⫹ H3AsO3 ⫹ H2O ⫽ 2 I ⫺ ⫹ H3AsO4 ⫹ 2 H⫹; use starch and KI as indicator. I2/2 ⫽ 126.9045

I⫺

2 I ⫺ ⫹ Br2(excess) ⫽ I2 ⫹ 2Br ⫺ Remove excess Br2 formic acid and titrate I2 with thiosulfate. I2/2 ⫽ 126.9045

IO3⫺

IO3⫺ ⫹ 5 I ⫺ (excess) ⫹ 6 H⫹ ⫽ 3 I2 ⫹ 3 H2O; titrate I2 with thiosulfate. KIO3/6 ⫽ 35.67

IO4

IO4⫺ ⫹ 7 I ⫺ (excess) ⫹ 8 H⫹ ⫽ 4 I2 ⫹ 4 H2O; use a neutral buffered solution. Titrate I2 with thiosulfate. KIO4/2 ⫽ 115.00

K

K2Na[Co(NO2)6]; dissolve in H2SO4 and titrate with either KMnO4 or Ce(IV). ca. K/5.5 but use an empirical factor.

Mg

Mg(oxine)2 ; dissolve precipitate and use procedure for Al(8-hydroxyquinoline)3 . Mg/8 ⫽ 3.0381

Mn(II)

2 Mn2⫹ ⫹ 5 BiO⫺3 ⫹ 14 H⫹ ⫽ 2 MnO4⫺ ⫹ 5 Bi3⫹ ⫹ 7 H2O 2 MnO⫺4 ⫹ 5 AsO33⫺ ⫹ 6 H⫹ ⫽ 2 Mn2⫹ ⫹ 5 AsO43 ⫺ ⫹ 3 H2O; Mn/5 ⫽ 10.9876

⫺

2 Mn2⫹ ⫹ 5 S2O28⫺ ⫹ 8 H2O (Ag⫹ catalyst) ⫽ 2 MnO4⫺ ⫹ 10 SO42 ⫺ ⫹ 16 H⫹ Titrate the permanganate formed with iron(II) as under iron(II); Mn/5 ⫽ 10.9876 2 Mn2⫹ ⫹ 5 IO4⫺ ⫹ 3 H2O ⫽ 2 MnO4⫺ ⫹ 5 IO3⫺ ⫹ 6 H⫹ Slowly precipitate excess KIO4 with Hg(NO3)2 . Filter, add excess Fe2⫹ and titrate excess with standard KMnO4 solution; Mn/5 ⫽ 10.9876 MnO4⫺ ⫹ 4 Mn2⫹ ⫹ 15 H2P2O72 ⫺ [pH range 4 to 7] ⫽ 5 Mn(H2P2 O7 )33 ⫺ ⫹ 4 H2O Use Pt 9 SCE indicator system; Mn/1 ⫽ 54.9380 Mn(IV)

MnO2 ⫹ 2 Fe2⫹(excesss standard) ⫹ 4 H⫹ ⫽ Mn2⫹ ⫹ 2 Fe3⫹ ⫹ 2 H2O (use CO2 atmosphere) MnO2 ⫹ H2C2O4(excess standard) ⫹ 2 H⫹ ⫽ Mn2⫹ ⫹ 2 CO2 ⫹ 2 H2O (use CO2 atmosphere) In either of the above, titrate excess with KMnO4 . Mn/2 ⫽ 27.469; MnO2/2 ⫽ 43.47

Mn(VI)

MnO24 ⫺ ⫹ 2H2C2O4 ⫹ 4 H⫹ ⫽ Mn2⫹ ⫹ 4 CO2 ⫹ 4 H2O Add excess oxalate and back-titrate with permanganate. Mn/4 ⫽ 13.7345

Mn(VII)

2 MnO4⫺ ⫹ 5H2C2O4 6 H⫹ ⫽ 2 Mn2⫹ ⫹ 10 CO2 ⫹ 3 H2O; Mn/5 ⫽ 10.9876

Mo

Mo(VI) ⫹ Zn ⫽ Mo(III) ⫹ Zn2⫹; catch eluate in excess Fe2(SO4)3 solution Mo(III) ⫹ 3 Fe3⫹ ⫹ 4 H2O ⫽ MoO42⫹ ⫹ 3 Fe2⫹ 8 H⫹; titrate Fe(II) with KMnO4 Mo/3 ⫽ 31.98 Mo(VI) ⫹ Ag ⫹ Cl ⫺ ⫽ Mo(V) ⫹ AgCl; pass through Ag reductor at 60– 80⬚C. Mo(V) ⫹ Ce(IV) ⫽ Mo(VI) ⫹ Ce(III); Mo/l ⫽ 95.94

N2H4

3 N2H4 ⫹ 2 BrO3⫺ (excess) ⫽ 3 N2 ⫹ 2 Br ⫺ ⫹ 6 H2O; add excess KI and titrate I2 with thiosulfate. N2H4/4 ⫽ 8.01

NH2OH

NH2OH ⫹ BrO3⫺ ⫽ NO3⫺ ⫹ Br ⫺ ⫹ H⫹ ⫹ H2O; proceed as above for N2H4 . NH2OH/6 ⫽ 5.505

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TABLE 11.29 Equations for the Redox Determinations of the Elements with Equivalent Weights (Continued) HN3

2 HN3 ⫹ 2 Ce(IV)(excess) ⫽ 3 N2 ⫹ 2 Ce(III) ⫹ 2 H⫹; done under inert atmosphere. Add excess KI and titrate with thiosulfate. HN3/1 ⫽ 43.03

NO2⫺

5 NO2⫺ ⫹ 2 MnO4⫺ (excess) ⫹ 6 H⫹ ⫽ 5 NO3⫺ ⫹ 2 Mn2⫹ ⫹ 3 H2O; determine excess KMnO4 standard Na2C2O4 solution. NaNO2/1 ⫽ 69.00

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NO2⫺ ⫹ 2 Ce(IV)(excess) ⫹ H2O ⫽ NO3⫺ ⫹ 2 Ce(III) ⫹ 2 H⫹; warmed to 50⬚C. Add excess standard Fe(II) solution and back-titrate with standard Ce(IV) using erioglaucine indicator. NaNO2/1 ⫽ 69.00 NO3⫺

NO3⫺ ⫹ excess Fe2⫹ (Mo catalyst) ⫹ 4H⫹ ⫽ NO ⫹ Fe3⫹. Add H3PO4 and back-titrate excess Fe(II) with K2Cr2O7 . NaNO3/3 ⫽ 28.34

Nb(V)

Nb(V) ⫹ Zn ⫽ Nb(III) ⫹ Zn2⫹; catch reduced solution under excess Fe(III). Nb(III) ⫹ 2 Fe3⫹ ⫽ Nb(V) ⫹ 2 Fe2⫹; titrate Fe(II) with MnO4 solution using 1,10-phenanthroline as indicator. Nb/2 ⫽ 46.453; Nb2O5 ⫽ 66.455

Ni

Precipitate Ni(anthranilate)2 and proceed as under Cd. Ni/8 ⫽ 7.336

O2

O2 ⫹ 2 Mn2⫹ ⫹ 2 OH ⫺ ⫽ 2 MnO2 ⫹ 2 H⫹; stoppered flask plus KI MnO2 ⫹ 2 I ⫺ ⫹ 4 H⫹ ⫽ Mn2⫹ ⫹ I2 2H2O; titrate I2 released with thiosulfate. O2/4 ⫽ 7.007

O3

O3 ⫹ 2 I ⫺ ⫹ H2O ⫽ O2 ⫹ I2 ⫹ 2 OH ⫺ ; acidify and titrate with thiosulfate. O3/2 ⫽ 24.00

H2O2

5 H2O2 ⫹ 2 MnO4⫺ ⫹ 6 H⫹ ⫽ 5 O2 ⫹ 2 Mn2⫹ ⫹ 8 H2O; H2O2/2 ⫽ 17.01 H2O2 ⫹ 2 Ce(IV) ⫹ 2 H⫹ ⫽ 2 Ce(III) ⫹ 2 H2O; use 1,10-phenanthroline indicator H2O2/1 ⫽ 34.02 H2O2 ⫹ 2 I ⫺ ⫹ 2 H⫹ ⫽ I2 ⫹ 2 H2O; titrate I2 with thiosulfate. H2O2/2 ⫽ 17.01 H2O2 ⫹ 2 Ti(III) ⫹ 2H⫹ ⫽ 2 Ti(IV) ⫹ 2H2O; end point is disappearance of the yellow color of peroxotitanic acid. H2O2/2 ⫽ 17.01

P

The yellow precipitate of (NH4)3[P(Mo3O10)4] is dissolved in NH4OH, then solution is strongly acidified with H2SO4 . See molybdenum; 12 moles Mo per P. P/36 ⫽ 0.86038

HPH2O2

HPH2O2 ⫹ 2 I2(excess) ⫹ 2 H2O ⫽ H3PO4 ⫹ 4 I ⫺ ⫹ 4 H⫹ (let stand 10 h) Make solution alkaline with NaHCO3 and titrate excess I2 with standard arsenite solution. HPH2O2/4 ⫽ 16.499

H3PO3

H3PO3 ⫹ I2(excess) ⫹ H2O ⫽ H3PO4 ⫹ 2 I ⫺ ⫹ 2 H⫹ (use CO2/NaHCO3 buffer; let stand 40– 60 min in stoppered flask). Titrate excess I2 with standard arsenite solution. H3PO3/2 ⫽ 41.00

Pb

Isolate Pb as PbSO4 , dissolve it in NaOAc and precipitate with K2Cr2O7 . Dissolve K2CrO4 in NaCl 9 HCl solution, add KI, and titrate I2 with thiosulfate solution. Pb/3 ⫽ 69.1; PbO/3 ⫽ 2 PbCrO4 ⫹ 6 I ⫺ ⫹ 16 H⫹ ⫽ 2 Pb2⫹ ⫹ 2 Cr3⫹ ⫹ 3 I2 ⫹ 8 H2O 74.4

S2 ⫺

H2S ⫹ I2(excess) ⫽ S ⫹ 2 I ⫺ ⫹ 2 H⫹ Back-titrate excess I2 with standard thiosulfate solution. S/2 ⫽ 16.03; H2S/2 ⫽ 17.04 H2S ⫹ 4 Br2 ⫹ 4 H2O ⫽ SO42 ⫺ ⫹ 8 Br ⫺ ⫹ 10 H⫹ Use excess KBr and standard KBrO3 solution. Let stand until clear, add excess KI, and titrate with standard thiosulfate solution. H2S/8 ⫽ 4.260; SO2/2 ⫽ 32.03; SCN/6 ⫽ 9.681

SO2 , SO23 ⫺

SO2 ⫹ I2 ⫹ 2 H2O ⫽ SO24 ⫺ ⫹ 2 I ⫺ ⫹ 4 H⫹ (Titrate excess I2 with standard thiosulfate) SO2/2 ⫽ 32.03 SO2 ⫹ 4 Br2 ⫹ 2 H2O ⫽ SO24 ⫺ ⫹ 2 Br ⫺ ⫹ 4 H⫹ (Titrate with standard KBrO3 9 KBr solution until methyl orange is bleached.) SO2/2 ⫽ 32.03

S2O23 ⫺

2 S2O32 ⫺ ⫹ I2 ⫽ S4O62 ⫺ ⫹ 2 I ⫺ (Use starch indicator)

H2SO5

SO25 ⫺ ⫹ H3AsO3 ⫽ SO42 ⫺ ⫹ H3AsO4

S2O82 ⫺

S2O28 ⫺ ⫹ H3AsO3 ⫹ H2O ⫽ 2 SO42 ⫺ ⫹ H3AsO4 ⫹ 2 H⫹ S2O28 ⫺ ⫹ 2 Fe2⫹ ⫽ 2 SO42 ⫺ ⫹ 2 Fe3⫹

Na2S2O3/1 ⫽ 158.11

H2SO5/2 ⫽ 57.04 H2S2O8/2 ⫽ 97.07

H2S2O8/2 ⫽ 97.07

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SECTION 11

TABLE 11.29 Equations for the Redox Determinations of the Elements with Equivalent Weights (Continued) Sb

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5 Sb(III) ⫹ 2 MnO4⫺ ⫹ 16 H⫹ ⫽ 5 Sb(V) ⫹ 2 Mn2⫹ ⫹ 8 H2O 3 Sb(III) ⫹ BrO3⫺ ⫹ 6 H⫹ ⫽ 3 Sb(V) ⫹ Br ⫺ ⫹ 3 H2O Sb(III) ⫹ I2 [tartrate buffer, pH ⬎7] ⫽ Sb(V) ⫹ 2 I ⫺ Sb(III) ⫹ 2 Ce(IV) ⫽ Sb(V) ⫹ 2 Ce(III) For all four methods: Sb/2 ⫽ 60.88; Sb2O3/4 ⫽ 72.88

SeO23 ⫺

5 H2SeO3 ⫹ 2 MnO4⫺ ⫹ 6 H⫹ ⫽ 5 H2SeO4 ⫹ 2 Mn2⫹ ⫹ 3 H2O

Na2SeO3/2 ⫽ 86.47

H2SeO3 ⫹ 4 I ⫺ ⫹ 4 H⫹ ⫽ Se ⫹ 2 I2 ⫹ 3 H2O (titrate I2 with standard thiosulfate solution) Na2SeO3/2 ⫽ 86.47 H2SeO3 ⫹ 4 S2O23 ⫺ ⫹ 4 H⫹ ⫽ SeS4O26 ⫺ ⫹ S4 O26 ⫺ ⫹ 3 H2O (add small excess of thiosulfate and back-titrate with standard iodine solution) Na2SeO3/4 ⫽ 47.23 SeO24 ⫺

SeO24 ⫺ ⫹ 2 H⫹ ⫹ 2 Cl ⫺ ⫽ SeO32 ⫺ ⫹ Cl2 ⫹ H2O (absorb Cl2 in KI solution) Cl2 ⫹ 2 I ⫺ ⫽ 2 Cl ⫺ ⫹ I2 (titrate I2 with standard thiosulfate) Na2SeO4/2 ⫽ 94.47

Sn(IV)

SnCl26 ⫺ ⫹ Pb ⫽ Sn2⫹ ⫹ Pb2⫹ ⫹ 6 Cl ⫺ (in CO2 atmosphere boil 40 min) Sn2⫹ ⫹ I2 ⫹ 6 Cl ⫺ ⫽ SnCl26 ⫺ ⫹ 2 I ⫺ (at 0– 3⬚C) Sn/2 ⫽ 59.35; SnO2/2 ⫽ 67.35

Sn(II)

Sn(II) ⫹ 2 Ce(IV) ⫽ Sn(IV) ⫹ 2 Ce(III)

Te(IV)

3 H2TeO3 ⫹ Cr2O27 ⫺ ⫹ 8 H⫹ ⫽ 3 H2TeO4 ⫹ 2 Cr3⫹ ⫹ 4 H2O

Te(VI)

H2TeO4 ⫹ 2 Cl ⫹ 2 H ⫽ H2TeO3 ⫹ Cl2 ⫹ H2O (see SeO )

Ti

2 Ti(IV) ⫹ Zn(reductor) ⫽ 2Ti(III) ⫹ Zn(II) Ti(III) ⫹ Fe3⫹ ⫽ Ti(IV) ⫹ Fe2⫹ (in CO2 atmosphere; use KSCN as indicator) 47.88 or Ti(III) ⫹ Methylene blue ⫽ Ti(IV) ⫹ colorless leuco base (in CO2 atmosphere) 47.88

Tl

⫺

Sn/2 ⫽ 59.35

⫹

2 Tl⫹ ⫹ MnO4⫺ ⫹ 8 H⫹ ⫽ 2 Tl3⫹ ⫹ Mn2⫹ ⫹ 4 H2O

Te/2 ⫽ 63.80

2⫺ 4

Te/2 ⫽ 63.80 Ti/1 ⫽ Ti/1 ⫽

Tl/2 ⫽ 102.19

Tl⫹ ⫹ 2 Ce3⫹ ⫽ Tl3⫹ ⫹ 2 Ce3⫹ (to a yellow color or use 1,10-phenanthroline) 102.19

Tl/2 ⫽

U

U(VI) ⫹ Zn ⫽ U(III) ⫹ U(IV) ⫹ Zn(II) [pass air through solution to oxidize U(III) to U(IV)] 5 U4⫹ ⫹ 2 MnO4⫺ ⫹ 2 H2O ⫽ 5 UO22⫹ ⫹ 2 Mn2⫹ ⫹ 4 H⫹ U/2 ⫽ 119.01; U3O8/6 ⫽ 140.35

V

Oxidize V(IV) to V(V) with permanganate. Destroy excess with sodium azide and boiling. VO⫹2 ⫹ Fe2⫹ ⫹ 2 H⫹ ⫽ VO2⫹ ⫹ Fe3⫹ ⫹ H2O (diphenyaminesulfonic acid indicator) V/1 ⫽ 50.94 Reduce V(V) with SO2 and bubble CO2 through boiling solution to remove excess SO2. 5 VO2⫹ ⫹ MnO4⫺ ⫹ H2O ⫽ 5 VO2⫹ ⫹ Mn2⫹ ⫹ 2 H⫹ V/1 ⫽ 50.94 Reduce V(V) to V(II) with Zn; catch eluate in excess Fe3⫹. V2⫹ ⫹ 2 Fe3⫹ ⫹ H2O ⫽ VO2⫹ ⫹ 2 Fe2⫹ ⫹ 2 H⫹ Titrate VO2⫹ 9 Fe2⫹ mixture with permanganate to VO2⫹ 9 Fe3⫹ 30.32

Zn

V/3 ⫽ 16.98; V2O5/6 ⫽

Dissolve precipitate of Zn[Hg(SCN)4] in 4M HCl in stoppered flask, add CHCl3 . Zn/24 ⫽ 2.725 2 SCN ⫺ ⫹ 3 IO3⫺ ⫹ 2 H⫹ ⫹ CN ⫺ ⫽ 2 SO42 ⫺ ⫹ 3 ICN ⫹ H2O 2 Fe(CN)63 ⫺ ⫹ 2 I ⫺ ⫹ 3 Zn2⫹ ⫹ 2 K2⫹ ⫽ K2Zn3[Fe(CN)6]2 ⫹ I2 Remove I2 as formed by standard thiosulfate solution. 3Zn/2 ⫽ 98.07 but empirical value of 99.07 is recommended. Precipitate Zn(anthranilate)2 ; proceed as with Cd.

Zn/8 ⫽ 8.174

Note: Additional procedural information plus interferences and general remarks will be found in J. A. Dean, ed., Analytical Chemistry Handbook, McGraw-Hill, New York, 1995.

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Precipitation Titrations

Many precipitation reactions that are useful as separation techniques for gravimetric analysis fail to meet one or both of two requirements for titrimetry: 1. The reaction rate must be sufficiently rapid, particularly in the titration of dilute solutions and in the immediate vicinity of the end point. To increase the precipitation rate, it is sometimes beneficial to change solvents or to raise the temperature. By adding an excess of reagent and backtitrating, it may be possible to take advantage of a more rapid precipitation in the reverse direction. By choosing an end-point detection method that does not require equilibrium to be reached in the immediate vicinity of the end point, advantage may be taken of a faster reaction rate at points removed from the end point. Examples are: amperometric titrations, conductometric titrations, and photometric titrations. 2. The stoichiometry must be exact. Coprecipitation by solid-solution formation, foreign ion entrapment, and adsorption are possible sources of error. Table 11.30 lists standard solutions for precipitation titrations and Table 11.31 lists specific reagents as indicators, adsorption indicators, and protective colloids for precipitation titrations.

11.6.6

Complexometric Titrations

A complexometric titration is based on the essentially stoichiometric reaction of a complexing agent (chelon) with another species to form a complex species (chelonate) that is only slightly dissociated and is soluble in the titration medium. In such a titration, either the chelon or the chelonate may serve as the limiting reagent (that is, as the titrant). The end point is detected by measuring or observing some property that reflects the change, in the vicinity of the equivalence point, in the concentration of the chelon or the chelonate. Examples of the application of metal-ion indicators are listed in Table 11.32. For a metal indicator to be useful, a proper sequence of effective stabilities must be met. On the one hand, the metal-indicator complex must be sufficiently stable to maintain itself in extremely dilute solution; otherwise the end-point color change will be spread over a broad interval of the titration, owing to the extended dissociation. On the other hand, the metal-indicator complex must be less stable than the metal chelonate; otherwise a sluggish end point, a late end point, or no end point at all will be obtained. Furthermore, the metal-indicator complex must react rapidly with the chelon. Only a limited number of the numerous chromogenic agents for metals allow this sequence and have useful indicator properties in chelometric titrations. Among the complexing agents that find use as titrating agents, ethylenediamine-N,N,N⬘,N⬘-tetraacetic acid (acronym EDTA, and equation abbreviation, H4Y) is by far the more important, and it is used in the vast majority of complexometric titrations. The successive acid pKa values of H4Y are pK1 ⫽ 2.0, pK2 ⫽ 2.67, pK3 ⫽ 6.16, pK4 ⫽ 10.26 at 20⬚C and an ionic strength of 0.1. The fraction ␣4 present as the tetravalent anion is of particular importance in equilibrium calculations. Its magnitude at various pH values is given in Table 11.33. The formation constants of EDTA complexes are gathered in Table 11.34. Based on their stability, the EDTA complexes of the most common metal ions may be roughly divided into three groups: log K ⬎ 20

Tri- and tetravalent cations including Bi, Fe(III), Ga, Hg(II), In, Sc, Th, U(IV), V(III), and Zr

log K ⫽ 15 to 18

Divalent transition metals, rare earths, and Al

log K ⫽ 8 to 11

Alkaline earths and Mg

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The more stable the metal complex, the lower the pH at which it can be quantitatively formed. Elements in the first group may be titrated with EDTA at pH 1 to 3 without interference from cations of the last two groups, while cations of the second group may be titrated at pH 4 to 5 without interference from the alkaline earths. In practice, an auxiliary complexing (masking) agent is usually added during EDTA titrations to prevent the precipitation of heavy metals as hydroxides or basic salts. The concentration of auxiliary complexing agents is generally high compared with the metal-ion concentration, and the solution is sufficiently well buffered so that the hydrogen ions produced during complexing of a metal ion by H4Y do not cause an appreciable change in pH. Many EDTA titrations are carried out in ammonia– ammonium chloride buffers, which serve also to provide ammonia as an auxiliary complexing agent. The cumulative formation constants of ammine complexes are listed in Table 11.35. 11.6.6.1 Types of Chelometric Titrations. Chelometric titrations may be classified according to their manner of performance: direct titrations, back titrations, substitution titrations, redox titrations, or indirect methods. 11.6.6.1.1 Direct Titrations. The most convenient and simplest manner is the measured addition of a standard chelon solution to the sample solution (brought to the proper conditions of pH, buffer, etc.) until the metal ion is stoichiometrically chelated. Auxiliary complexing agents such as citrate, tartrate, or triethanolamine are added, if necessary, to prevent the precipitation of metal hydroxides or basic salts at the optimum pH for titration. For example, tartrate is added in the direct titration of lead. If a pH range of 9 to 10 is suitable, a buffer of ammonia and ammonium chloride is often added in relatively concentrated form, both to adjust the pH and to supply ammonia as an auxiliary complexing agent for those metal ions which form ammine complexes. A few metals, notably iron(III), bismuth, and thorium, are titrated in acid solution. Direct titrations are commonly carried out using disodium dihydrogen ethylenediaminetetraacetate, Na2H2Y, which is available in pure form. The reaction of the chelon with the indicator must be rapid for a practical, direct titration. Where it is slow, heating of the titration medium is often expedient, or another indicator is employed. 11.6.6.1.2 Back Titrations. In the performance of a back titration, a known, but excess quantity of EDTA or other chelon is added, the pH is now properly adjusted, and the excess of the chelon is titrated with a suitable standard metal salt solution. Back titration procedures are especially useful when the metal ion to be determined cannot be kept in solution under the titration conditions or where the reaction of the metal ion with the chelon occurs too slowly to permit a direct titration, as in the titration of chromium(III) with EDTA. Back titration procedures sometimes permit a metal ion to be determined by the use of a metal indicator that is blocked by that ion in a direct titration. For example, nickel, cobalt, or aluminum form such stable complexes with Eriochrome Black T that the direct titration would fail. However, if an excess of EDTA is added before the indicator, no blocking occurs in the back titration with a magnesium or zinc salt solution. These metal ion titrants are chosen because they form EDTA complexes of relatively low stability, thereby avoiding the possible titration of EDTA bound by the sample metal ion. In a back titration, a slight excess of the metal salt solution must sometimes be added to yield the color of the metal-indicator complex. Where metal ions are easily hydrolyzed, the complexing agent is best added at a suitable, low pH and only when the metal is fully complexed is the pH adjusted upward to the value required for the back titration. In back titrations, solutions of the following metal ions are commonly employed: Cu(II), Mg, Mn(II), Pb(II), Th(IV), and Zn. These solutions are usually prepared in the approximate strength desired from their nitrate salts (or the solution of the metal or its oxide or carbonate in nitric acid), and a minimum amount of acid is added to repress hydrolysis of the metal ion. The solutions are then standardized against an EDTA solution (or other chelon solution) of known strength.

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11.6.6.1.3 Substitution Titrations. Upon the introduction of a substantial or equivalent amount of the chelonate of a metal that is less stable than that of the metal being determined, a substitution occurs, and the metal ion displaced can be titrated by the chelon in the same solution. This is a direct titration with regard to its performance, but in terms of the mechanism it can be considered as a substitution titration (or replacement titration). In principle any ion can be used if it forms a weaker EDTA complex than the metal ion being determined. Still weaker metal-EDTA complexes would not interfere. Exchange reactions are also possible with other metal complexes to permit application of the chelometric titration to non-titrable cations and anions. The exchange reagent can be added and the titration performed in the sample solution without prior removal of the excess reagent. A most important example is the exchange of silver ion with an excess of the tetracyanonickelate ion according to the equation:

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2 Ag⫹ ⫹ Ni(CN)24⫺ N 2 Ag(CN)⫺2 ⫹ Ni2⫹ The nickel ion freed may then be determined by an EDTA titration. Note that two moles of silver are equivalent to one mole of nickel and thus to one mole of EDTA. 11.6.6.1.4 Redox Titrations. Redox titrations can be carried out in the presence of excess EDTA. Here EDTA acts to change the oxidation potential by forming a more stable complex with one oxidation state than with the other. Generally the oxidized form of the metal forms a more stable complex than the reduced form, and the couple becomes a stronger reducing agent in the presence of excess EDTA. For example, the Co(III)–Co(II) couple is shifted about 1.2 volts, so that Co(II) can be titrated with Ce(IV). Alternatively, Co(III) can be titrated to Co(II), with Cr(II) as a reducing agent. Manganese(II) can be titrated directly to Mn(III) using hexacyanoferrate(III) as the oxidant. Alternatively, Mn(III), prepared by oxidation of the Mn(II)–EDTA complex with lead dioxide, can be determined by titration with standard iron(II) sulfate. 11.6.6.1.5 Indirect Procedures. Numerous inorganic anions that do not form complexes with a complexing agent are accessible to a chelatometric titration by indirect procedures. Frequently the anion can be precipitated as a compound containing a stoichiometric amount of a titrable cation. Another indirect approach employing replacement mechanism is the reduction of a species with the liquid amalgam of a metal that can be determined by a chelometric titration after removal of excess amalgam. For example: 2 Ag⫹ ⫹ Cd(Hg) ⫽ Cd2⫹ ⫹ 2 Ag(Hg) The equivalent amount of cadmium ion exchanged for the silver ion can readily be determined by EDTA titration procedures. 11.6.6.2 Preparation of Standard Solutions 11.6.6.2.1 Standard EDTA Solutions. Disodium dihydrogen ethylenediaminetetraacetate dihydrate is available commercially of analytical reagent purity. After drying at 80⬚C for at least 24 hr, its composition agrees exactly with the dihydrate formula (molecular weight 372.25). It may be weighed directly. If an additional check on the concentration is required, it may be standardized by titration with nearly neutralized zinc chloride or zinc sulfate solution. 11.6.6.2.2 Standard Magnesium Solution. Dissolve 24.647 g of magnesium sulfate heptahydrate in water and dilute to 1 L for 0.1M solution. 11.6.6.2.3 Standard Manganese(II) Solution. Dissolve exactly 16.901 g ACS reagent grade manganese(II) sulfate hydrate in water and dilute to 1 L. 11.6.6.2.4 Standard Zinc Solution. Dissolve exactly 13.629 g of zinc chloride, ACS reagent grade, or 28.754 g of zinc sulfate heptahydrate, and dilute to 1 L for 0.1000M solution.

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11.6.6.2.5 Buffer Solution, pH 10. Add 142 mL of concentrated ammonia solution (sp. grav. 0.88– 0.90) to 17.5 g of analytical reagent ammonium chloride, and dilute to 250 mL. 11.6.6.2.6 Water. Distilled water must be (a) redistilled in an all-Pyrex glass apparatus or (b) purified by passage through a column of cation exchange resin in the sodium form. For storage, polyethylene bottles are most satisfactory, particularly for very dilute (0.001M) EDTA solutions. 11.6.6.2.7 Murexide Indicator. Suspend 0.5 g of powdered murexide in water, shake thoroughly, and allow the undissolved solid to settle. Use 5–6 drops of the supernatant liquid for each titration. Decant the old supernatant liquid daily and treat the residue with water to provide a fresh solution of the indicator. Alternatively, grind 0.1 g of murexide with 10 g of ACS reagent grade sodium chloride; use about 50 mg of the mixture for each titration. 11.6.6.2.8 Pyrocatechol Violet Indicator Solution. Dissolve 0.1 g of the solid dyestuff in 100 mL of water.

11.6.7

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Masking Agents

Masking (and demasking) techniques are widely used in analytical chemistry because they frequently provide convenient and elegant methods by which to avoid the effects of unwanted components of a system without having to resort to physical separation. The best molecules or ligands to use as masking agents are those that are chemically stable and nontoxic and react rapidly to form strong, colorless complexes with the ions to be masked, but form only relatively weak complexes with other ions that are present. Tables 11.36 and 11.37 are intended as qualitative guides to the types of masking agents likely to be suitable for particular analytical problems. Masking must not be identified solely with complex formation. There are numerous complex compounds in which solutions show no masking effects. On the other hand, examples can be cited in which the product of soluble principal valence compounds may lead to masking. This latter category includes the annulment of the base action of NH2 9 groups in carboxylic acids by the addition of formaldehyde, the masking of the iodometric oxidation of sulfites by formaldehyde, as well as the masking of almost all reactions of molybdenum(VI), tungsten(VI), and vanadium(V) by hydrogen peroxide or fluoride ion. Sometimes the masking agent changes the valence state of the metal ion. Examples include the reduction of Fe(III) to Fe(II) with hydrazine, hydroxylamine hydrochloride, or tin(II) chloride. Hydroxylamine also reduces Ce(IV) to Ce(III), Cu(II) to Cu(I), and Hg(II) to free Hg. Ascorbic acid reduces Cu(II) to Cu(I) in the presence of the chloride ion. The reaction of the hydrogen sulfite ion in an alkaline solution with ketones and aldehydes is: H2C" O ⫹ HSO⫺3 N H2C(OH)SO⫺3 The carbon-oxygen double bond of the carbonyl group is opened, and the hydrogen sulfite radical is added. An increase in temperature reverses the reaction more easily for ketones than for aldehydes. Certain organic substances have no charge at any pH but form complexes with substances that do have a charge. The sugars and polyalcohols form such complexes in the pH range between 9 and 10 with a number of anions; including borate, molybdate, and arsenite. Elegant ion exchange methods have been devised for the sugars. Probably the most extensively applied masking agent is cyanide ion. In alkaline solution, cyanide forms strong cyano complexes with the following ions and masks their action toward EDTA: Ag, Cd, Co(II), Cu(II), Fe(II), Hg(II), Ni, Pd(II), Pt(II), Tl(III), and Zn. The alkaline earths, Mn(II), Pb, and the rare earths are virtually unaffected; hence, these latter ions may be titrated with EDTA with the former ions masked by cyanide. Iron(III) is also masked by cyanide. However, as the hexacyanoferrate(III) ion oxidizes many indicators, ascorbic acid is added to form hexacyanoferrate(II) ion. Moreover, since the addition of cyanide to an acidic solution results in the formation of deadly

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hydrogen cyanide, the solution must first be made alkaline, with hydrous oxide formation prevented by the addition of tartrate. Zinc and cadmium may be demasked from their cyanide complexes by the action of formaldehyde. Masking by oxidation or reduction of a metal ion to a state which does not react with EDTA is occasionally of value. For example, Fe(III) (log KMY ⫽ 24.23) in acidic media may be reduced to Fe(II) (log KMY ⫽ 14.33) by ascorbic acid; in this state iron does not interfere in the titration of some trivalent and tetravalent ions in strong acidic medium (pH 0 to 2). Similarly, Hg(II) can be reduced to the metal. In favorable conditions, Cr(III) may be oxidized by alkaline peroxide to chromate which does not complex with EDTA. In resolving complex metal-ion mixtures, more than one masking or demasking process may be utilized with various aliquots of the sample solution, or applied simultaneously or stepwise with a single aliquot. In favorable cases, even four or five metals can be determined in a mixture by the application of direct and indirect masking processes. Of course, not all components of the mixture need be determined by chelometric titrations. For example, redox titrimetry may be applied to the determination of one or more of the metals present.

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Demasking

For the major part, masking reactions that occur in solutions and lead to soluble compounds are equilibrium reactions. They usually require the use of an excess of the masking agent and can be reversed again by removal of the masking agent. The freeing of previously masked ionic or molecular species has been called demasking. This merits consideration in regard to its use in analysis. Masking never completely removes certain ionic or molecular species, but only reduces their concentrations. The extent of this lowering determines which color or precipitation reactions can be prevented. A system masked against a certain reagent is not necessarily masked against another but more aggressive reagent. It is therefore easy to see that masked reaction systems can also function as reagents at times (e.g., Fehling’s solution, Nessler’s reagent). The methods used in demasking are varied. One approach is to change drastically the hydrogen ion concentration of the solution. The conditional stability constants of most metal complexes depend greatly on pH, so that simply raising or lowering the pH is frequently sufficient for selective demasking. In most cases a strong mineral acid is added, and the ligand is removed from the coordination sphere of the complex through the formation of a slightly ionized acid, as with the polyprotic (citric, tartaric, EDTA, and nitriloacetic) acids. Another type of demasking involves formation of new complexes or other compounds that are more stable than the masked species. For example, boric acid is used to demask fluoride complexes of tin(IV) and molybdenum(VI). Formaldehyde is often used to remove the masking action of cyanide ions by converting the masking agent to a nonreacting species through the reaction: CN⫺ ⫹ HCHO N OCH2CN which forms glycollic nitrile. Pertinent instances are the demasking of Ni(CN)24⫺ ions to Ni2⫹ ions by formaldehyde and the demasking of dimethylglyoxime (dmg) from Pd(dmg)22⫺ ions by cyanide. Selectivity is evident in that Zn(CN)24⫺ is demasked whereas Cu(CN)23⫺ is not. Destruction of the masking ligand by chemical reaction may be possible, as in the oxidation of EDTA in acid solutions by permanganate or another strong oxidizing agent. Hydrogen peroxide and Cu(II) ion destroy the tartrate complex of aluminum. Demasking methods for a number of masking agents are enumerated in Table 11.38. short standard long

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TABLE 11.30 Standard Solutions for Precipitation Titrations The list given below includes the substances that are most used and most useful for the standardization of solutions for precipitation titrations. Primary standard solutions are denoted by the letter (P) in Column 1.

Standard

Formula weight

AgNO3 (P)

169.89

BaCl2 · 2H2O

244.28

Hg(NO3)2 · H2O

342.62

KBr

119.01

K4[Fe(CN)]6 · 3H2O

422.41

KSCN

97.18

K2SO4 (P)

174.26

NaCl (P)

58.44

NaF (P)

41.99

Na2SO4 (P)

142.04

Th(NO3)4 · 4H2O

552.12

Preparation Weigh the desired amount of ACS reagent grade* AgNO3 , dried at 105⬚C for 2 hr, and dissolve in double distilled water. Store in amber container and away from light. Check against NaCl. Dissolve clear crystals of the salt in distilled water. Standardize against K2SO4 or Na2SO4 . Dissolve the reagent grade salt in distilled water and dilute to desired volume. Standardize against NaCl. The commercial reagent (ACS) may contain 0.2% chloride. Prepare an aqueous solution of approximately the desired concentration and standardize it against AgNO3 . Dissolve the high-purity commercial salt in distilled water containing 0.2 g/L of Na2CO3 . Kept in an amber container and away from direct sunlight, solutions are stable for a month or more. Standardize against zinc metal. Prepare aqueous solutions having the concentration desired. Standardize against AgNO3 solution. Protect from direct sunlight. Dissolve about 17.43 g, previously dried at 150⬚C and accurately weighed, in distilled water and dilute exactly to 1 L. Dry at 130– 150⬚C and weigh accurately, from a closed container, 5.844 g, dissolve in water, and dilute exactly to 1 L. Dry at 110⬚C and weigh the appropriate amount of ACS reagent. Dissolve in water and dilute exactly to 1 L. Weigh accurately 14.204 g, dried at 150⬚C, and dissolve in distilled water. Dilute to exactly 1 L. Weigh the appropriate amount of crystals and dissolve in water. Standardize against NaF.

* Meets standards of purity (and impurity) set by the American Chemical Society.

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TABLE 11.31 Indicators for Precipitation Titrations Indicator

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Preparation and use Specific reagents

NH4Fe(SO4)2 · 12H2O

K2CrO4

Tetrahydroxy-1,4-benzoquinone (THQ)

Use reagent (ACS)* grade salt, low in chloride. Dissolve 175 g in 100 mL 6 M HNO3 which has been gently boiled for 10 min to expel nitrogen oxides. Dilute with 500 mL water. Use 2 mL per 100 mL of end-point volume. Use reagent (ACS)* grade salt, low in chloride. Prepare 0.1M aqueous solution (19.421 g/L). Use 2.5 mL per 100 mL of endpoint volume. Prepare fresh as required by dissolving 15 mg in 5 mL of water. Use 10 drops for each titration. Adsorption indicators

Bromophenol blue 2⬘,7⬘-Dichlorofluorescein Eosin, tetrabromofluorescein Fluorescein Potassium rhodizonate, C4O4(OK)2 Rhodamine 6G Sodium 3-alizarinsulfonate Thorin

Dissolve 0.1 g of the acid in 200 mL 95% ethanol. Dissolve 0.1 g of the acid in 100 mL 70% ethanol. Use 1 mL for 100 mL of initial solution. See Dichlorofluorescein. Dissolve 0.4 g of the acid in 200 mL 70% ethanol. Use 10 drops. Prepare fresh as required by dissolving 15 mg in 5 mL of water. Use 10 drops for each titration. Dissolve 0.1 g in 200 mL 70% ethanol. Prepare a 0.2% aqueous solution. Use 5 drops per 120 mL endpoint volume. Prepare a 0.025% aqueous solution. Use 5 drops. Protective colloids

Dextrin Polyethylene glycol 400

Use 5 mL of 2% aqueous solution of chloride-free dextrin per 25 mL of 0.1M halide solution. Prepare a 50% (v/v) aqueous solution of the surfactant. Use 5 drops per 100 mL end-point volume.

*Meets standards as set forth in Reagent Chemicals, American Chemical Society, Washington, D.C.; revised periodically.

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Chemical name

Calmagite 0.05 g/100 mL water; stable 1 year Eriochrome Black T 0.1 g/100 mL water; prepare fresh daily

1-(6-Hydroxy-m-tolylazo)2-naphthol-4-sulfonic acid

Murexide Suspend 0.5 g in water; use fresh supernatent liquid each day PAN

1-(2-Hydroxy-1-naphthylazo)-6-nitro-2-naphthol4-sulfonic acid

5-[(Hexahydro-2,4,6-trioxo5-pyrimidinyl)imino]2,4,6(1H,3H,5H)-pyrimidinetrione monoammonium salt 1-(2-Pyridylazo)-2-naphthol

Salicylic acid

2-Hydroxybenzoic acid

Xylenol orange

3,3’-Bis[N,N-di(carboxyethyl)aminomethyl]-ocresolsulfonephthalein

Wine-red

H4In ⫺ (red-violet); pK2 ⫽ 9.2 H3In2 ⫺ (violet); pK3 ⫽ 10.9 H2In3 ⫺ (blue)

Red with Ca2⫹ Yellow with Co2⫹, Ni2⫹, and Cu2⫹

HIn (orange-red); pK1 ⫽ 12.3 In ⫺ (pink)

Red

H4In (red); pK1 ⫽ 0.2 H3In ⫺ (yellow): pK2 ⫽ 7.8 H2In2 ⫺ (violet); pK3 ⫽ 9.8 HIn3 ⫺ (red-purple); pK4 ⫽ 11.7 H2In; pK1 ⫽ 2.98 HIn ⫺ ; pK2 ⫽ 12.38 9 COOH groups: pK3 ⫽ 0.76; pK4 ⫽ 1.15; pK5 ⫽ 2.58; pK6 ⫽ 3.23

Wine-red

Blue, except red with Th(IV) FeSCN2⫹ at pH 3 is reddishbrown

Titrations performed with Eriochrome Black T as indicator may be carried out equally well with Calmagite Direct titration: Ba, Ca, Cd, In, Mg, Mn, Pb, Sc, Sr, Tl, Zn, and lanthanides Back titration: Al, Ba, Bi, Ca, Co, Cr, Fe, Ga, Hg, Mn, Ni, Pb, Pd, Sc, Tl, V Substitution titration: Au, Ba, Ca, Cu, Hg, Pb, Pd, Sr Direct titration: Ca, Co, Cu, Ni Back titration: Ca, Cr, Ga Substitution titration: Ag, Au, Pd

Direct titration: Cd, Cu, In, Sc, Tl, Zn Back titration: Cu, Fe, Ga, Ni, Pb, Sc, Sn, Zn Substitution titration: Al, Ca, Co, Fe, Ga, Hg, In, Mg, Mn, Ni, Pb, V, Zn Direct titration: Al, Bi, Cd, Co, Fe, Ga, Mg, Mn, Ni, Pb, Th, Zn Back titration: Al, Bi, Fe, Ga, In, Ni, Pd, Sn, Th, Ti Typical uses: Fe(III) titrated with EDTA to colorless iron-EDTA complex Typical uses: Bi, Pb, Th

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Pyrocatecholsulfonephthalein

H2In ⫺ (red); pK2 ⫽ 8.1 HIn2 ⫺ (blue); pK3 ⫽ 12.4 In3 ⫺ (orange) H2In ⫺ (red); pK2 ⫽ 6.3 HIn2 ⫺ (blue); pK3 ⫽ 11.5 In3⫺ (yellow-orange)

Applications

LEFT

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Colors of metal-indicator complexes

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Indicator

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TABLE 11.32 Properties and Applications of Selected Metal Ion Indicators

Source: J. A. Dean, ed., Analytical Chemistry Handbook, McGraw-Hill, New York, 1995.

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TABLE 11.33 Variation of ␣4 with pH pH

⫺log ␣4

pH

⫺log ␣4

2.0 2.5 3.0 4.0 5.0 6.0

13.44 11.86 10.60 8.48 6.45 4.66

7.0 8.0 9.0 10.0 11.0 12.0

3.33 2.29 1.29 0.46 0.07 0.00

TABLE 11.34 Formation Constants of EDTA Complexes at 25⬚C, Ionic Strength Approaching Zero Metal ion

log KMY

Metal ion

log KMY

Co(III) V(III) In Fe(III) Th Sc Cr(III) Bi Tl(III) Sn(II) Ti(III) Hg(II) Ga Zr Cu(II) Ni Pd(II) Pb(II) V(V)

36 25.9 24.95 24.23 23.2 23.1 23 22.8 22.5 22.1 21.3 21.80 20.25 19.40 18.7 18.56 18.5 18.3 18.05

V(IV) U(IV) Ti(IV) Ce(III) Zn Cd Co(II) Al La Fe(II) Mn(II) Cr(II) V(II) Ca Be Mg Sr Ba Ag

18.0 17.5 17.3 16.80 16.4 16.4 16.31 16.13 16.34 14.33 13.8 13.6 12.7 11.0 9.3 8.64 8.80 7.78 7.32

TABLE 11.35 Cumulative Formation Constants of Ammine Complexes at 20⬚C, Ionic Strength 0.1 Cation

log K1

log K2

log K3

log K4

log K5

log K6

Cadmium Cobalt(II) Cobalt(III) Copper(I) Copper(II) Iron(II) Manganese(II) Mercury(II) Nickel Platinum(II) Silver(I) Zinc

2.65 2.11 6.7 5.93 4.31 1.4 0.8 8.8 2.80

4.75 3.74 14.0 10.86 7.98 2.2 1.3 17.5 5.04

6.19 4.79 20.1

7.12 5.55 25.7

6.80 5.73 30.8

5.14 5.11 35.2

11.02

13.32

12.66

18.5 6.77

19.28 7.96

8.71

3.24 2.37

7.05 4.81

7.31

9.46

8.74 35.3

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TABLE 11.36 Masking Agents for Various Elements Element Ag Al

As Au Ba Be Bi Ca Cd Ce Co

Cr

Cu

Fe

Ga Ge Hf Hg In Ir La Mg Mn

Mo

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Masking agent Br⫺, citrate, Cl⫺, CN⫺, I⫺, NH3 , SCN⫺, S2O23⫺, thiourea, thioglycolic acid, diethyldithiocarbamate, thiosemicarbazide, bis(2-hydroxyethyl)dithiocarbamate Acetate, acetylacetone, BF⫺4 , citrate, C2O42⫺, EDTA, F⫺, formate, 8-hydroxyquinoline-5-sulfonic acid, mannitol, 2,3-mercaptopropanol, OH⫺, salicylate, sulfosalicylate, tartrate, triethanolamine, tiron Citrate, 2,3-dimercaptopropanol, NH2OH · HCl, OH⫺, S22⫺, S2O32⫺, tartrate Br⫺, CN⫺, NH3 , SCN⫺, S2O23⫺, thiourea Citrate, cyclohexanediaminetetraacetic acid, N,N-dihydroxyethylglycine, EDTA, F⫺, SO24⫺, tartrate Acetylacetone, citrate, EDTA, F⫺, sulfosalicylate, tartrate Br⫺, citrate, Cl⫺, 2,3-dimercaptopropanol, dithizone, EDTA, I⫺, OH⫺, Na5P3O10 , SCN⫺, tartrate, thiosulfate, thiourea, triethanolamine BF⫺4 , citrate, N,N-dihydroxyethylglycine, EDTA, F⫺, polyphosphates, tartrate Citrate, CN⫺, 2,3-dimercaptopropanol, dimercaptosuccinic acid, dithizone, EDTA, glycine, I⫺, malonate, NH3 , 1,10-phenanthroline, SCN⫺, S2O23⫺, tartrate Citrate, N,N-dihydroxyethylglycine, EDTA, F⫺, PO34⫺, reducing agents (ascorbic acid), tartrate, tiron Citrate, CN⫺, diethyldithiocarbamate, 2,3-dimercaptopropanol, dimethylglyoxime, ethylenediamine, EDTA, F⫺, glycine, H2O2 , NH3 , NO⫺2 , 1,10-phenanthroline, Na5P3O10 , SCN⫺, S2O23⫺, tartrate Acetate, (reduction with) ascorbic acid ⫹ KI, citrate, N,N-dihydroxyethylglycine, EDTA, F⫺, formate, NaOH ⫹ H2O2 , oxidation to CrO24⫺, Na5P3O10 , sulfosalicylate, tartrate, triethylamine, tiron Ascorbic acid ⫹ KI, citrate, CN⫺, diethyldithiocarbamate, 2,3-dimercaptopropanol, ethylenediamine, EDTA, glycine, hexacyanocobalt(III)(3⫺), hydrazine, I⫺, NaH2PO2 , NH2OH · HCl, NH3 , NO2⫺ , 1,10-phenanthroline, S2⫺, SCN⫺ ⫹ SO32⫺, S2 O32⫺, sulfosalicylate, tartrate, thioglycolic acid, thiosemicarbazide, thiocarbohydrazide, thiourea Acetylacetone, (reduction with) ascorbic acid, C2O24⫺, citrate, CN⫺, 2,3-dimercaptopropanol, EDTA, F⫺, NH3 , NH2OH · HCl, OH⫺, oxine, 1,10-phenanthroline, 2,2’-bipyridyl, PO34⫺, P2O74⫺, S2⫺, SCN⫺, SnCl2 , S2O32⫺, sulfamic acid, sulfosalicylate, tartrate, thioglycolic acid, thiourea, tiron, triethanolamine, trithiocarbonate Citrate, Cl⫺, EDTA, OH⫺, oxalate, sulfosalicylate, tartrate F⫺, oxalate, tartrate See Zr Acetone, (reduction with) ascorbic acid, citrate, Cl⫺, CN⫺, 2,3-dimercaptopropan-1-ol, EDTA, formate, I⫺, SCN⫺, SO23⫺, tartrate, thiosemicarbazide, thiourea, triethanolamine Cl⫺, EDTA, F⫺, SCN⫺, tartrate, thiourea, triethanolamine Citrate, CN⫺, SCN⫺, tartrate, thiourea Citrate, EDTA, F⫺, oxalate, tartrate, tiron Citrate, C2O24⫺, cyclohexane-1,2-diaminetetraacetic acid, N,N-dihydroxyethylglycine, EDTA, F⫺, glycol, hexametaphosphate, OH⫺, P2O47⫺, triethanolamine Citrate, CN⫺, C2O24⫺, 2,3-dimercaptopropanol, EDTA, F⫺, Na5P3O10 , oxidation to MnO4⫺ , P2O47⫺, reduction to Mn(II) with NH2OH · HCl or hydrazine, sulfosalicylate, tartrate, triethanolamine, triphosphate, tiron Acetylacetone, ascorbic acid, citrate, C2O24⫺, EDTA, F⫺, H2O2 , hydrazine, mannitol, Na5P3O10 , NH2OH · HCl, oxidation to molybdate, SCN⫺, tartrate, tiron, triphosphate

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TABLE 11.36 Masking Agents for Various Elements (Continued) Element Nb Nd NH4⫹ Ni

Np Os Pa Pb Pd Pt Pu Rare earths Re Rh Ru Sb Sc Se Sn Sr Ta Te Th Ti Tl U V W Y Zn

Zr

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Masking agent Citrate, C2O42⫺, F⫺, H2O2 , OH⫺, tartrate EDTA HCHO Citrate, CN⫺, N,N-dihydroxyethylglycine, dimethylglyoxime, EDTA, F⫺, glycine, malonate, Na5P3O10 , NH3 , 1,10-phenanthroline, SCN⫺, sulfosalicylate, thioglycolic acid, triethanolamine, tartrate F⫺ CN⫺, SCN⫺, thiourea H2O2 Acetate, (C6H5)4AsCl, citrate, 2,3-dimercaptopropanol, EDTA, I⫺, Na5P3O10 , SO24⫺, S2O32⫺, tartrate, tiron, tetraphenylarsonium chloride, triethanolamine, thioglycolic acid Acetylacetone, citrate, CN⫺, EDTA, I⫺, NH3 , NO⫺2 , SCN⫺, S2O32⫺, tartrate, triethanol amine Citrate, CN⫺, EDTA, I⫺, NH3 , NO⫺2 , SCN⫺, S2O32⫺, tartrate, urea Reduction to Pu(IV) with sulfamic acid C2O24⫺, citrate, EDTA, F⫺, tartrate Oxidation to perrhenate Citrate, tartrate, thiourea CN⫺, thiourea Citrate, 2,3-dimercaptopropanol, EDTA, F⫺, I⫺, OH⫺, oxalate, S2⫺, S22⫺, S2O32⫺, tartrate, triethanolamine Cyclohexane-1,2-diaminetetraacetic acid, F⫺, tartrate Citrate, F⫺, I⫺, reducing agents, S2⫺, SO23⫺, tartrate Citrate, C2O32⫺, 2,3-dimercaptopropanol, EDTA, F⫺, I⫺, OH⫺, oxidation with bromine water, phosphate(3⫺), tartrate, triethanolamine, thioglycolic acid Citrate, N,N-dihydroxyethylglycine, EDTA, F⫺, SO24⫺, tartrate Citrate, F⫺, H2O2 , OH⫺, oxalate, tartrate Citrate, F⫺, I⫺, reducing agents, S2⫺, sulfite, tartrate Acetate, acetylacetone, citrate, EDTA, F⫺, SO24⫺, 4-sulfobenzenearsonic acid, sulfosalicylic acid, tartrate, triethanolamine Ascorbic acid, citrate, F⫺, gluconate, H2O2 , mannitol, Na5P3O10 , OH⫺, SO24⫺, sulfosalicylic acid, tartrate, triethanolamine, tiron Citrate, Cl⫺, CN⫺, EDTA, HCHO, hydrazine, NH2OH · HCl, oxalate, tartrate, triethanolamine Citrate, (NH4)2CO3 , C2O24⫺, EDTA, F⫺, H2O2 , hydrazine ⫹ triethanolamine, phosphate(3⫺), tartrate (Reduction with) ascorbic acid, hydrazine, or NH2OH · HCl, CN⫺, EDTA, F⫺, H2O2 , mannitol, oxidation to vanadate, triethanolamine, tiron Citrate, F⫺, H2O2 , hydrazine, Na5P3O10 , NH2OH · HCl, oxalate, SCN⫺, tartrate, tiron, triphosphate, oxidation to tungstate(VI) Cyclohexane-1,2-diaminetetraacetic acid, F⫺ Citrate, CN⫺, N,N-dihydroxyethylglycine, 2,3-dimercaptopropanol, dithizone, EDTA, F⫺, glycerol, glycol, hexacyanoferrate(II)(4⫺), Na5P3O10 , NH3 , OH⫺, SCN⫺, tartrate, triethanolamine Arsenazo, carbonate, citrate, C2O24⫺, cyclohexane-1,2-diaminetetraacetic acid, EDTA, F⫺, H2O2 , PO34⫺, P2O74⫺, pyrogallol, quinalizarinesulfonic acid, salicylate, SO42⫺ ⫹ H2O2 , sulfosalicylate, tartrate, triethanolamine

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TABLE 11.37 Masking Agents for Anions and Neutral Molecules Anion or neutral molecule Boric acid Br⫺ Br2 BrO⫺3 Chromate(VI) Citrate Cl⫺ Cl2 ClO⫺3 ClO⫺4 CN⫺ EDTA F⫺ Fe(CN)36⫺ Germanic acid I⫺ I2 IO⫺3 IO⫺4 MnO⫺4 MoO24⫺ NO⫺2 Oxalate Phosphate S S2⫺ Sulfate Sulfite SO25⫺ Se and its anions Te Tungstate Vanadate

Masking agent F⫺, glycol, mannitol, tartrate, and other hydroxy acids Hg(II) Phenol, sulfosalicylic acid Reduction with arsenate(III), hydrazine, sulfite, or thiosulfate Reduction with arsenate(III), ascorbic acid, hydrazine, hydroxylamine, sulfite, or thiosulfate Ca(II) Hg(II), Sb(III) Sulfite Thiosulfate Hydrazine, sulfite HCHO, Hg(II), transition metal ions Cu(II) Al(III), Be(II), boric acid, Fe(III), Th(IV), Ti(IV), Zr(IV) Arsenate(III), ascorbic acid, hydrazine, hydroxylamine, thiosulfate Glucose, glycerol, mannitol Hg(II) Thiosulfate Hydrazine, sulfite, thiosulfate Arsenate(III), hydrazine, molybdate(VI), sulfite, thiosulfate Reduction with arsenate(III), ascorbic acid, azide, hydrazine, hydroxylamine, oxalic acid, sulfite, or thiosulfate Citrate, F⫺, H2O2 , oxalate, thiocyanate ⫹ Sn(II) Co(II), sulfamic acid, sulfanilic acid, urea Molybdate(VI), permanganate Fe(III), tartrate CN⫺, S2⫺, sulfite Permanganate ⫹ sulfuric acid, sulfur Cr(III) ⫹ heat HCHO, Hg(II), permanganate ⫹ sulfuric acid Ascorbic acid, hydroxylamine, thiosulfate Diaminobenzidine, sulfide, sulfite I⫺ Citrate, tartrate Tartrate

TABLE 11.38 Common Demasking Agents Abbreviations: DPC, diphenylcarbazide; HDMG, dimethylglyoxime; PAN, 1-(2-pyridylazo)-2-naphthol. Complexing agent CN⫺

Ion demasked

Demasking agent

Ag⫹ Cd2⫹

H⫹ H⫹ HCHO ⫹ OH⫺

Cu⫹ Cu2⫹ Fe2⫹ Fe3⫹

H⫹ HgO Hg2⫹ HgO

Application Precipitation of Ag Free Cd2⫹ Detection of Cd (with DPC) in presence of Cu Precipitation of Cu Determination of Cu Free Fe2⫹ Determination of Fe

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TABLE 11.38 Common Demasking Agents (Continued) Complexing agent CN⫺ (continued)

Ion demasked HDMG Hg2⫹ Ni2⫹

Demasking agent Pd2⫹ Pd2⫹ HCHO H⫹ HgO Ag⫹

CO23⫺ C2O24⫺ Cl⫺ (concentrated) Ethylenediamine

Cu2⫹ Al3⫹ Ag⫹ Ag⫹

Ag⫹, Hg2⫹, Pb2⫹ H⫹ HgO Cl3CCHO · H2O H⫹ H⫹ OH⫺ H2O SiO2 (amorphous)

EDTA

Al3⫹ Ba2⫹ Co2⫹

F⫺ H⫹ Ca2⫹

Mg2⫹ Th(IV) Ti(IV) Zn2⫹ Many ions Al(III)

F⫺ SO24⫺ Mg2⫹ CN⫺ KMO⫺4 Be(II)

Fe(III) Hf(IV) Mo(VI) Sn(IV) U(VI)

OH⫺ OH⫺ Al(III) or Be(II) H3BO3 H3BO3 Al(III)

Pd2⫹ Zn2⫹

F⫺

Zr(IV) H2O2 NH3

Hf(IV), Ti(IV), or Zr Ag⫹

Al(III) or Be(II) Ca(II) OH⫺ Fe(III) Br⫺ H⫹ I⫺ SiO2 (amorphous)

NO⫺2 PO34⫺

Co(III) Fe(III) UO22⫺

H⫹ OH⫺ Al(III)

SCN⫺ SO24⫺ (conc. H2SO4) S2O32⫺

Fe(III) Ba2⫹ Ag⫹ Cu2⫹ Al(III)

OH⫺ H2O H⫹ OH⫺ H2O2 ⫹ Cu2⫹

Tartrate

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Application Detection of CN⫺ (with Ni2⫹) Detection of Pd (with DPC) Detection of Ni (with HDMG) Free Ni2⫹ Determination of Ni Detection and determination of Ni (with HDMG) in presence of Co Detection of Ag, Hg, Pb (with HDMG) Precipitation of Pd Determination of Pd Titration of Zn with EDTA Free Zn Free Cu2⫹ Precipitation of Al(OH)3 Precipitation of AgCl Differentiation of crystalline and amorphous SiO2 (with CrO24⫺) Titration of Al Precipitation of BaSO4 (with SO24⫺) Detection of Co (with diethyldithiocarbamate) Titration of Mg, Mn Titration of Th Precipitation of Ti (with NH3) Titration of Mg, Mn, Zn Free ions Precipitation of Al (with 8-hydroxylquinoline) Precipitation of Al(OH)3 Precipitation of Fe(OH)3 Detection of Hg (with xylenol orange) Free molybdate Precipitation of Sn (with H2S) Detection of U (with dibenzoylmethane) Detection of Zr (with xylenol orange) Detection of Ca (with alizarin S) Precipitation of Zr(OH)4 Free ions Detection of Br⫺ Detection of Ag Detection of I and Br Differentiation of crystalline and amorphous SiO2 (with CrO24⫺) Free Co Precipitation of FePO4 Detection of U (with dibenzoylmethane) Precipitation of Fe(OH)3 Precipitation of BaSO4 Free Ag⫹ Detection of Cu (with PAN) Precipitation of Al(OH)3

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TABLE 11.39 Amino Acids pI and pKa Values This table lists the pKa and pI (pH at the isoelectric point) values of ␣-amino acids commonly found in proteins along with their abbreviations. The dissociation constants refer to aqueous solutions at 25⬚C. Abbreviations

pKa values

Name

3 Letter

1 Letter

9 COOH

9 NH⫹3

Alanine Arginine Asparagine Aspartic acid Cysteine Glutamine Glutamic acid Glycine Histidine Isoleucine Leucine Lysine Methionine Phenylalanine Proline Serine Threonine Tryptophan Tyrosine Valine

Ala Arg Asn Asp Cys Gln Glu Gly His Ile Leu Lys Met Phe Pro Ser Thr Trp Tyr Val

A R N D C Q E G H I L K M F P S T W Y V

2.34 2.17 2.01 1.89 1.96 2.17 2.19 2.34 1.82 2.36 2.36 2.18 2.28 1.83 1.99 2.21 2.09 2.83 2.20 2.32

9.69 9.04 8.80 9.60 10.28 9.13 9.67 9.60 9.17 9.60 9.60 8.98 9.21 9.13 10.60 9.15 9.10 9.39 9.11 9.62

Other groups

12.48 3.65 8.18 4.25 6.00 5.98 10.53

10.07

pI values 6.00 10.76 5.41 2.77 5.07 5.65 3.22 5.97 7.59 6.02 9.74 5.74 5.48 6.30 5.68 5.60 5.89 5.66 5.96

Source: E. L. Smith, et al., Principles of Biochemistry, 7th ed., McGraw-Hill, New York, 1983; H. J. Hinz, ed., Thermodynamic Data for Biochemistry and Biotechnology, Springer-Verlag, Heidelberg, 1986.

TABLE 11.40 Tolerances of Volumetric Flasks Tolerances,* ⫾mL

Tolerances,* ⫾mL

Capacity, mL

Class A

Class B

Capacity, mL

Class A

Class B

5 10 25 50 100

0.02 0.02 0.03 0.05 0.08

0.04 0.04 0.06 0.10 0.16

200 250 500 1000 2000

0.10 0.12 0.20 0.30 0.50

0.20 0.24 0.40 0.60 1.00

*Accuracy tolerances for volumetric flasks at 20⬚C are given by ASTM standard E288.

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TABLE 11.41 Pipet Capacity Tolerances Volumetric transfer pipets

Measuring and serological pipets Tolerances,† ⫾mL

Tolerances,* ⫾mL Capacity, mL

Class A

Class B

Capacity, mL

Class B

0.5 1 2 3 4 5 10 15 20 25 50 100

0.006 0.006 0.006 0.01 0.01 0.01 0.02 0.03 0.03 0.03 0.05 0.08

0.012 0.012 0.012 0.02 0.02 0.02 0.04 0.06 0.06 0.06 0.10 0.16

0.1 0.2 0.25 0.5 0.6 1 2 5 10 25

0.005 0.008 0.008 0.01 0.01 0.02 0.02 0.04 0.06 0.10

* Accuracy tolerances for volumetric transfer pipets are given by ASTM standard E969 and Federal Specification NNN-P395. † Accuracy tolerances for measuring pipets are given by Federal Specification NNN-P-350 and for serological pipets by Federal Specification NNN-P-375.

TABLE 11.42 Tolerances of Micropipets (Eppendorf) Capacity, ␮L

Accuracy, %

Precision, %

Capacity, ␮L

Accuracy, %

Precision, %

10 40 50 60 70 80

1.2 0.6 0.5 0.5 0.5 0.5

0.4 0.2 0.2 0.2 0.2 0.2

100 250 500 600 900 1000

0.5 0.5 0.5 0.5 0.5 0.5

0.2 0.15 0.15 0.15 0.15 0.15

TABLE 11.43 Buret Accuracy Tolerances Accuracy, ⫾mL

Capacity, mL

Subdivision, mL

Class A* and precision grade

Class B and standard grade

10 25 50 100

0.05 0.10 0.10 0.20

0.02 0.03 0.05 0.10

0.04 0.06 0.10 0.20

* Class A conforms to specifications in ASTM E694 for standard taper stopcocks and to ASTM E287 for Teflon or polytetrafluoroethylene stopcock plugs. The 10-mL size meets the requirements for ASTM D664.

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TABLE 11.44 Factors for Simplified Computation of Volume The volume is determined by weighing the water, having a temperature of t⬚C, contained or delivered by the apparatus at the same temperature. The weight of water, w grams, is obtained with brass weights in air having a density of 1.20 mg/mL. For apparatus made of soft glass, the volume contained or delivered at 20⬚C is given by

␯20 ⫽ wƒ20 mL where ␯20 is the volume at 20⬚ and ƒ20 is the factor (apparent specific volume) obtained from the table below for the temperature t at which the calibration is performed. The volume at any other temperature t⬘ may then be obtained from

␯⬘ ⫽ ␯20[1 ⫹ 0.00002(t⬘ ⫺ 20)] mL For apparatus made of any other material, the volume contained or delivered at the temperature t is

␯t ⫽ wft mL where w is again the weight in air obtained with brass weights (in grams), and ft is the factor given in the third column of the table for the temperature t. The volume at any temperature t⬘ may then be obtained from

␯t⬘ ⫽ ␯t[1 ⫹ ␤(t⬘ ⫺ t)] mL where ␤ is the cubical coefficient of thermal expansion of the material from which the apparatus is made. Approximate values of ␤ for some frequently encountered materials are given in Table 11.45. t, ⬚C

ƒ20

ƒt

t, ⬚C

ƒ20

ƒt

0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19

1.001 62 54 48 43 41 1.001 39 40 42 45 50 1.001 56 63 72 82 93 1.002 06 20 35 51 68

1.001 22 16 12 09 09 1.001 09 12 16 21 28 1.001 36 45 56 68 81 1.001 96 1.002 12 29 47 66

20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40

1.002 86 1.003 05 26 47 69 1.003 93 1.004 17 42 68 95 1.005 23 1.005 52 1.005 82 1.006 13 1.006 44 1.006 77 1.007 10 1.007 44 1.007 79 1.008 15 1.008 52

1.002 86 1.003 07 30 53 77 1.004 03 29 56 84 1.005 13 1.005 43 1.005 74 1.006 06 1.006 39 1.006 72 1.007 07 1.007 42 1.007 78 1.008 15 1.008 53 1.008 91

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TABLE 11.45 Cubical Coefficients of Thermal Expansion This table lists values of ␤, the cubical coefficient of thermal expansion, taken from “Essentials of Quantitative Analysis,” by Benedetti-Pichler, and from various other sources. The value of ␤ represents the relative increases in volume for a change in temperature of 1⬚C at temperatures in the vicinity of 25⬚C, and is equal to 3␣, where ␣ is the linear coefficient of thermal expansion. Data are given for the types of glass from which volumetic apparatus is most commonly made, and also for some other materials which have been or may be used in the fabrication of apparatus employed in analytical work.

␤

Material Glasses Alkali-resistant, Corning 728 Gerateglas, Schott G20 Kimble KG-33 (borosilicate) N-51A (“Resistant”) R-6 (soft) Pyrex, Corning 744 Vitreous silica Vycor, Corning 790 Metals Brass Copper Gold Monel metal Platinum Silver Stainless steel Tantalum Tungsten Plastics and other materials Hard rubber Polyethylene Polystyrene Porcelain Teflon (polytetrafluoroethylene)

1.90 ⫻ 10⫺5 1.47 0.96 1.47 2.79 0.96 0.15 0.24 ca. 5.5 5.0 4.3 4.0 2.7 5.7 ca. 5.3 ca. 2.0 1.3 24 ⫻ 10⫺5 45– 90 18– 24 ca. 1.2 16.5

TABLE 11.46 General Solubility Rules for Inorganic Compounds Nitrates Acetates Chlorides Sulfates Hydrogen sulfates Carbonates, phosphates, chromates, silicates Hydroxides Sulfides Sodium, potassium, ammonium Silver

All nitrates are soluble. All acetates are soluble; silver acetate is moderately soluble. All chlorides are soluble except AgCl, PbCl2 , and Hg2Cl2 . PbCl2 is soluble in hot water, slightly soluble in cold water. All sulfates are soluble except barium and lead. Silver, mercury(I), and calcium are only slightly soluble. The hydrogen sulfates are more soluble than the sulfates. All carbonates, phosphates, chromates, and silicates are insoluble, except those of sodium, potassium, and ammonium. An exception is MgCrO4 which is soluble. All hydroxides (except lithium, sodium, potassium, cesium, rubidium, and ammonia) are insoluble; Ba(OH)2 is moderately soluble; Ca(OH)2 and Sr(OH)2 are slightly soluble. All sulfides (except alkali metals, ammonium, magnesium, calcium, and barium) are insoluble. Aluminum and chromium sulfides are hydrolyzed and precipitate as hydroxides. All sodium, potassium, and ammonium salts are soluble. Exceptions: Na4Sb2O7 , K2NaCo(NO2)6 , K2PtCl6 , (NH4)2PtCl6 , and (NH4)2NaCo(NO2)6 . All silver salts are insoluble. Exceptions: AgNO3 and AgClO4 ; AgC2H3O2 and Ag2SO4 are moderately soluble.

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TABLE 11.47 Concentrations of Commonly Used Acids and Bases Freshly opened bottles of these reagents are generally of the concentrations indicated in the table. This may not be true of bottles long opened and this is especially true of ammonium hydroxide, which rapidly loses its strength. In preparing volumetric solutions, it is well to be on the safe side and take a little more than the calculated volume of the concentrated reagent, since it is much easier to dilute a concentrated solution than to strengthen one that is too weak. A concentrated C.P. reagent usually comes to the laboratory in a bottle having a label which states its molecular weight w, its density (or its specific gravity) d, and its percentage assay p. When such a reagent is used to prepare an aqueous solution of desired molarity M, a convenient formula to employ is V⫽

100 wM pd

where V is the number of milliliters of concentrated reagent required for 1 liter of the dilute solution. Example: Sulfuric acid has the molecular weight 98.08. If the concentrated acid assays 95.5% and has the specific gravity 1.84, the volume required for 1 liter of a 0.1 molar solution is V⫽

100 ⫻ 98.08 ⫻ 0.1 ⫽ 5.58 mL 95.5 ⫻ 1.84

Reagent

Formula Weight

Density, g · mL⫺1 (20⬚C)

Weight % (approx)

Acetic acid Ammonium hydroxide (as NH3 ) Ethylenediamine Formic acid Hydrazine Hydriodic acid Hydrobromic acid Hydrochloric acid Hydrofluoric acid Nitric acid Perchloric acid Phosphoric acid Pyridine Potassium hydroxide (soln) Sodium hydroxide (soln) Sulfuric acid Triethanolamine

60.05 35.05 17.03 60.10 46.03 32.05 127.91 80.92 36.46 20.0 63.01 100.47 97.10 79.10 56.11 40.00 98.08 149.19

1.05 0.90

99.8 56.6 28.0 100 90.5 95 57 48 37.2 49.0 70.4 70.5 85.5 100 45 50.5 96.0 100

0.899 1.20 1.011 1.70 1.49 1.19 1.18 1.42 1.67 1.70 0.982 1.46 1.54 1.84 1.124

Molarity

V, mL*

17.45 14.53

57.3 60.0

15.0 23.6 30.0 7.6 8.84 12.1 28.9 15.9 11.7 14.8 12.4 11.7 19.4 18.0 7.53

66.7 42.5 33.3 132 113 82.5 34.5 63.0 85.5 67.5 80.6 85.5 51.5 55.8 132.7

* V, mL ⫽ volume in milliliters needed to prepare 1 liter of 1 molar solution.

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TABLE 11.48 Standard Stock Solutions* Element Aluminum Antimony

Arsenic

Barium

Beryllium Bismuth Boron Bromine Cadmium Calcium Cerium

Cesium

Chlorine Chromium Cobalt Copper

Dysprosium Erbium Europium Fluorine Gadolinium Gallium Germanium

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Procedure Dissolve 1.000 g Al wire in minimum amount of 2 M HCl; dilute to volume. Dissolve 1.000 g Sb in (1) 10 ml HNO3 plus 5 ml HCl, and dilute to volume when dissolution is complete; or (2) 18 ml HBr plus 2 ml liquid Br2 ; when dissolution is complete add 10 ml HClO4 , heat in a well-ventilated hood while swirling until white fumes appear and continue for several minutes to expel all HBr, then cool and dilute to volume. Dissolve 1.3203 g of As2O3 in 3 ml 8 M HCl and dilute to volume; or treat the oxide with 2 g NaOH and 20 ml water; after dissolution dilute to 200 ml, neutralize with HCl (pH meter), and dilute to volume. (1) Dissolve 1.7787 g BaCl2 · 2H2O (fresh crystals) in water and dilute to volume. (2) Dissolve 1.516 g BaCl2 (dried at 250⬚C for 2 hr) in water and dilute to volume. (3) Treat 1.4367 g BaCO3 with 300 ml water, slowly add 10 ml of HCl and, after the CO2 is released by swirling, dilute to volume. (1) Dissolve 19.655 g BeSO4 · 4H2O in water, add 5 ml HCl (or HNO3 ), and dilute to volume. (2) Dissolve 1.000 g Be in 25 ml 2 M HCl, then dilute to volume. Dissolve 1.000 g Bi in 8 ml of 10 M HNO3 , boil gently to expel brown fumes, and dilute to volume. Dissolve 5.720 g fresh crystals of H3BO3 and dilute to volume. Dissolve 1.489 g KBr (or 1.288 g NaBr) in water and dilute to volume. (1) Dissolve 1.000 g Cd in 10 ml of 2 M HCl; dilute to volume. (2) Dissolve 2.282 g 3CdSO4 · 8H2O in water; dilute to volume. Place 2.4973 g CaCO3 in volumetric flask with 300 ml water, carefully add 10 ml HCl; after CO2 is released by swirling, dilute to volume. (1) Dissolve 4.515 g (NH4 )4Ce(SO4 )4 · 2H2O in 500 ml water to which 30 ml H2SO4 had been added, cool, and dilute to volume. Advisable to standardize against As2O3 . (2) Dissolve 3.913 g (NH4 )2Ce(NO3 )6 in 10 ml H2SO4 , stir 2 min, cautiously introduce 15 ml water and again stir 2 min. Repeat addition of water and stirring until all the salt has dissolved, then dilute to volume. Dissolve 1.267 g CsCl and dilute to volume. Standardize: Pipette 25 ml of final solution to Pt dish, add 1 drop H2SO4 , evaporate to dryness, and heat to constant weight at ⬎ 800⬚C. Cs (in ␮g/ml) ⫽ (40)(0.734)(wt of residue) Dissolve 1.648 g NaCl and dilute to volume. (1) Dissolve 2.829 g K2Cr2O7 in water and dilute to volume. (2) Dissolve 1.000 g Cr in 10 ml HCl, and dilute to volume. Dissolve 1.000 g Co in 10 ml of 2 M HCl, and dilute to volume. (1) Dissolve 3.929 g fresh crystals of CuSO4 · 5H2O, and dilute to volume. (2) Dissolve 1.000 g Cu in 10 ml HCl plus 5 ml water to which HNO3 (or 30%H2O2 ) is added dropwise until dissolution is complete. Boil to expel oxides of nitrogen and chlorine, then dilute to volume. Dissolve 1.1477 g Dy2O3 in 50 ml of 2 M HCl; dilute to volume. Dissolve 1.1436 g Er2O3 in 50 ml of 2 M HCl; dilute to volume. Dissolve 1.1579 g Eu2O3 in 50 ml of 2 M HCl; dilute to volume. Dissolve 2.210 g NaF in water and dilute to volume. Dissolve 1.152 g Gd2O3 in 50 ml of 2 M HCl; dilute to volume. Dissolve 1.000 g Ga in 50 ml of 2 M HCl; dilute to volume. Dissolve 1.4408 g GeO2 with 50 g oxalic acid in 100 ml of water; dilute to volume.

* 1000 ␮g/mL as the element in a final volume of 1 liter unless stated otherwise. From J. A. Dean and T. C. Rains, “Standard Solutions for Flame Spectrometry,” in Flame Emission and Atomic Absorption Spectrometry, J. A. Dean and T. C. Rains (Eds.), Vol. 2, Chap. 13, Marcel Dekker, New York, 1971.

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TABLE 11.48 Standard Stock Solutions (Continued) Element Gold

Hafnium Holmium Indium Iodine Iridium

Iron Lanthanum Lead Lithium Lutetium Magnesium Manganese

Mercury Molybdenum Neodymium Nickel Niobium

Osmium

Palladium Phosphorus Platinum Potassium Praseodymium Rhenium Rhodium Rubidium Ruthenium Samarium Scandium

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Procedure Dissolve 1.000 g Au in 10 ml of hot HNO3 by dropwise addition of HCl, boil to expel oxides of nitrogen and chlorine, and dilute to volume. Store in amber container away from light. Transfer 1.000 g Hf to Pt dish, add 10 ml of 9 M H2SO4 , and then slowly add HF dropwise until dissolution is complete. Dilute to volume with 10% H2SO4 . Dissolve 1.1455 g Ho2O3 in 50 ml of 2 M HCl; dilute to volume. Dissolve 1.000 g In in 50 ml of 2 M HCl; dilute to volume. Dissolve 1.308 g Kl in water and dilute to volume. (1) Dissolve 2.465 g Na3IrCl6 in water and dilute to volume. (2) Transfer 1.000 g Ir sponge to a glass tube, add 20 ml of HCl and 1 ml of HClO4 . Seal the tube and place in an oven at 300⬚C for 24 hr. Cool, break open the tube, transfer the solution to a volumetric flask, and dilute to volume. Observe all safety precautions in opening the glass tube. Dissolve 1.000 g Fe wire in 20 ml of 5 M HCl; dilute to volume. Dissolve 1.1717 g La2O3 (dried at 110⬚C) in 50 ml of 5 M HCl, and dilute to volume. (1) Dissolve 1.5985 g Pb(NO3 )2 in water plus 10 ml HNO3 , and dilute to volume. (2) Dissolve 1.000 g Pb in 10 ml HNO3 , and dilute to volume. Dissolve a slurry of 5.3228 g Li2CO3 in 300 ml of water by addition of 15 ml HCl; after release of CO2 by swirling, dilute to volume. Dissolve 1.6079 g LuCl3 in water and dilute to volume. Dissolve 1.000 g Mg in 50 ml of 1 M HCl and dilute to volume. (1) Dissolve 1.000 g Mn in 10 ml HCl plus 1 ml HNO3 , and dilute to volume. (2) Dissolve 3.0764 g MnSO4 · H2O (dried at 105⬚C for 4 hr) in water and dilute to volume. (3) Dissolve 1.5824 g MnO2 in 10 HCl in a good hood, evaporate to gentle dryness, dissolve residue in water and dilute to volume. Dissolve 1.000 g Hg in 10 ml of 5 M HNO3 and dilute to volume. (1) Dissolve 2.0425 g (NH4 )2MoO4 in water and dilute to volume. (2) Dissolve 1.5003 g MoO3 in 100 ml of 2 M ammonia, and dilute to volume. Dissolve 1.7373 g NdCl3 in 100 ml 1 M HCl and dilute to volume. Dissolve 1.000 g Ni in 10 ml hot HNO3 , cool, and dilute to volume. Transfer 1.000 g Nb (or 1.4305 g Nb2O5 ) to Pt dish, add 20 ml HF, and heat gently to complete dissolution. Cool, add 40 ml H2SO4 , and evaporate to fumes of SO3 . Cool and dilute to volume with 8 M H2SO4 . Dissolve 1.3360 g OsO4 in water and dilute to 100 ml. Prepare only as needed as solution loses strength on standing unless Os is reduced by SO2 and water is replaced by 100 ml 0.1 M HCl. Dissolve 1.000 g Pd in 10 ml of HNO3 by dropwise addition of HCl to hot solution; dilute to volume. Dissolve 4.260 g (NH4 )2HPO4 in water and dilute to volume. Dissolve 1.000 g Pt in 40 ml of hot aqua regia, evaporate to incipient dryness, add 10 ml HCl and again evaporate to moist residue. Add 10 ml HCl and dilute to volume. Dissolve 1.9067 g KCl (or 2.8415 g KNO3 ) in water and dilute to volume. Dissolve 1.1703 g Pr2O3 in 50 ml of 2 M HCl; dilute to volume. Dissolve 1.000 g Re in 10 ml of 8 M HNO3 in an ice bath until initial reaction subsides, then dilute to volume. Dissolve 1.000 g Rh by the sealed-tube method described under iridium. Dissolve 1.4148 g RbCl in water. Standardize as described under cesium. Rb (in ␮g/ml) ⫽ (40)(0.320)(wt of residue). Dissolve 1.317 g RuO2 in 15 ml of HCl; dilute to volume. Dissolve 1.1596 g Sm2O3 in 50 ml of 2 M HCl; dilute to volume. Dissolve 1.5338 g Sc2O3 in 50 ml of 2 M HCl; dilute to volume.

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TABLE 11.48 Standard Stock Solutions (Continued) Element Selenium Silicon

Silver Sodium Strontium Sulfur Tantalum

Tellurium Terbium Thallium Thorium Thulium Tin Titanium Tungsten Uranium Vanadium Ytterbium Yttrium Zinc Zirconium

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Procedure Dissolve 1.4050 g SeO2 in water and dilute to volume or dissolve 1.000 g Se in 5 ml of HNO3 , then dilute to volume. Fuse 2.1393 g SiO2 with 4.60 g Na2CO3 , maintaining melt for 15 min in Pt crucible. Cool, dissolve in warm water, and dilute to volume. Solution contains also 2000 ␮g/ ml sodium. (1) Dissolve 1.5748 g AgNO3 in water and dilute to volume. (2) Dissolve 1.000 g Ag in 10 ml of HNO3 ; dilute to volume. Store in amber glass container away from light. Dissolve 2.5421 g NaCl in water and dilute to volume. Dissolve a slurry of 1.6849 g SrCO3 in 300 ml of water by careful addition of 10 ml of HCl; after release of CO2 by swirling, dilute to volume. Dissolve 4.122 g (NH4 )2SO4 in water and dilute to volume. Transfer 1.000 g Ta (or 1.2210 g Ta2O5 ) to Pt dish, add 20 ml of HF, and heat gently to complete the dissolution. Cool, add 40 ml of H2SO4 and evaporate to heavy fumes of SO3 . Cool and dilute to volume with 50% H2SO4 . (1) Dissolve 1.2508 g TeO2 in 10 ml of HCl; dilute to volume. (2) Dissolve 1.000 g Te in 10 ml of warm HCl with dropwise addition of HNO3 , then dilute to volume. Dissolve 1.6692 g of TbCl3 in water, add 1 ml of HCl, and dilute to volume. Dissolve 1.3034 g TlNO3 in water and dilute to volume. Dissolve 2.3794 g Th(NO3 )4 · 4H2O in water, add 5 ml HNO3 , and dilute to volume. Dissolve 1.142 g Tm2O3 in 50 ml of 2 M HCl; dilute to volume. Dissolve 1.000 g Sn in 15 ml of warm HCl; dilute to volume. Dissolve 1.000 g Ti in 10 ml of H2SO4 with dropwise addition of HNO3 ; dilute to volume with 5% H2SO4 . Dissolve 1.7941 g of Na2WO4 · 2H2O in water and dilute to volume. Dissolve 2.1095 g UO2(NO3 )2 · 6H2O (or 1.7734 g uranyl acetate dihydrate) in water and dilute to volume. Dissolve 2.2963 g NH4VO3 in 100 ml of water plus 10 ml of HNO3 ; dilute to volume. Dissolve 1.6147 g YbCl3 in water and dilute to volume. Dissolve 1.2692 g Y2O3 in 50 ml of 2 M HCl and dilute to volume. Dissolve 1.000 g Zn in 10 ml of HCl; dilute to volume. Dissolve 3.533 g ZrOCl2 · 8H2O in 50 ml of 2 M HCl, and dilute to volume. Solution should be standardized.

General Reagents, Indicators, and Special Solutions

Unless otherwise stated, the term g per liter signifies grams of the formula indicated dissolved in water and made up to a liter of solution. Acetic acid, HC2H3O2 96N: 350 mL glacial acetic acid per liter. Alcohol, amyl, C5H11OH: use as purchased. Alcohol, ethyl, C2H5OH; 95% alcohol, as purchased. Alizarin, dihydroxyanthraquinone (indicator): dissolve 0.1 g in 100 mL alcohol; pH range yellow 5.5– 6.8 red. Alizarin yellow R, sodium p-nitrobenzeneazosalicylate (indicator): dissolve 0.1 g in 100 mL water; pH range yellow 10.1– violet 12.1.

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Alizarin yellow GG, salicyl yellow, sodium m-nitrobenzeneazosalicylate (indicator): dissolve 0.1 g in 100 mL 50% alcohol; pH range yellow 10.0–12.0 lilac.

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Alizarin S, alizarin carmine, sodium alizarin sulfonate (indicator): dissolve 0.1 g in 100 mL water; pH range yellow 3.7– 5.2 violet. Aluminon (qualitative test for aluminum). The reagent consists of 0.1% solution of the ammonium salt of aurin tricarboxylic acid. A bright red precipitate, persisting in alkaline solution, indicates aluminum. Aluminum chloride, AlCl3 90.5N: 22 g per liter. Aluminum nitrate, Al(NO3)3 · 7.5H2O90.5N: 58 g per liter. Aluminum sulfate, Al2(SO4)3 · 18H2O9 0.5N: 55 g per liter. Ammonium acetate, NH4C2H3O2 93N: 231 g per liter. Ammonium carbonate, (NH4)2CO3 · H2O9 3N: 171 g per liter; for the anhydrous salt: 144 g per liter. Ammonium chloride, NH4Cl93N: 161 g per liter. Ammonium hydroxide, NH4OH9 15N: the concentrated solution which contains 28% NH3 ; for 6N: 400 mL per liter. Ammonium molybdate, (NH4)2MoO4 9 N: dissolve 88.3 g of solid (NH4)6Mo7O24 · 4H2O in 100 mL 6N NH4OH. Add 240 g of solid NH4NO3 and dilute to 1 liter. Another method is to take 72 g of MoO3 , add 130 mL of water and 75 mL of 15N NH4OH; stir mechanically until nearly all has dissolved, then add it to a solution of 240 mL concentrated HNO3 and 500 mL of water; stir continuously while solutions are being mixed; allow to stand 3 days, filter, and use the clear filtrate. Ammonium nitrate, NH4NO3 9N: 80 g per liter. Ammonium oxalate, (NH4)2C2O4 · H2O9 0.5N: 40 g per liter. Ammonium polysulfide (yellow ammonium sulfide), (NH4)2Sx : allow the colorless (NH4)2S to stand, or add sulfur. Ammonium sulfate, (NH4)2SO4 90.5N: 33 g per liter; saturated: dissolve 780 g of (NH4)2SO4 in water and make up to a liter. Ammonium sulfide (colorless), (NH4)2S9saturated: pass H2S through 200 mL of concentrated NH4OH in the cold until no more gas is dissolved, add 200 mL NH4OH and dilute with water to a liter; the addition of 15 g of sulfur is sufficient to make the polysulfide. Antimony pentachloride, SbCl5 90.5N: 39 g per liter. Antimony trichloride, SbCl3 90.5N: 38 g per liter. Aqua regia: mix 3 parts of concentrated HCl and 1 part of concentrated HNO3 just before ready to use. Arsenic acid, H3AsO4 · 0.5H2O90.5N (⫽ 1⁄2H3AsO4 ⫼ 5): 15 g per liter. Arsenous oxide, As2O3 90.25N: 8 g per liter for saturation. Aurichloric acid, HAuCl4 · 3H2O: dissolve in ten parts of water. Aurin, see rosolic acid. Azolitmin solution (indicator); make up a 1% solution of azolitmin by boiling in water for 5 minutes; it may be necessary to add a small amount of NaOH to make the solution neutral; pH range red 4.5– 8.3 blue.

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Bang’s reagent (for glucose estimation): dissolve 100 g of K2CO3 , 66 g of KCl, and 160 of KHCO3 in the order given in about 700 mL of water at 30⬚C. Add 4.4 g of copper sulfate and dilute to 1 liter after the CO2 is evolved. This solution should be shaken only in such a manner as not to allow the entry of air. After 24 hours 300 mL diluted to a liter with saturated KCl solution, shaken gently and used after 24 hours; 50 mL # 10 mg glucose.

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Barfoed’s reagent (test for glucose): dissolve 66 g of cupric acetate and 10 mL of glacial acetic acid in water and dilute to 1 liter. Barium chloride, BaCl2 · 2H2O9 0.5N: 61 g per liter. Barium hydroxide, Ba(OH)2 · 8H2O90.2N: 32 g per liter for saturation. Barium nitrate, Ba(NO3)2 90.5N: 65 g per liter. Baudisch’s reagent: see cupferron. Benedict’s qualitative reagent (for glucose): dissolve 173 g of sodium citrate and 100 g of anhydrous sodium carbonate in about 600 mL of water, and dilute to 850 mL; dissolve 17.3 g of CuSO4 · 5H2O in 100 mL of water and dilute to 150 mL; this solution is added to the citratecarbonate solution with constant stirring. See also the quantitative reagent below. Benedict’s quantitative reagent (sugar in urine): This solution contains 18 g copper sulfate, 100 g of anhydrous sodium carbonate, 200 g of potassium citrate, 125 g of potassium thiocyanate, and 0.25 g of potassium ferrocyanide per liter; 1 mL of this solution # 0.002 g sugar. Benzidine hydrochloride solution (for sulfate determination): mix 6.7 g of benzidine [C12H8(NH2)2] or 8.0 g of the hydrochloride [C12H8(NH2)2 · 2HCl] into a paste with 20 mL of water; add 20 mL of HCl (sp. gr. 1.12) and dilute the mixture to 1 liter with water; each mL of this solution is equivalent to 0.00357 g H2SO4 . Benzopurpurine 4B (indicator): dissolve 0.1 g in 100 mL water; pH range blue-violet 1.3–4.0 red. Benzoyl auramine (indicator): dissolve 0.25 g in 100 mL methyl alcohol; pH range violet 5.0– 5.6 pale yellow. Since this compound is not stable in aqueous solution, hydrolyzing slowly in neutral medium, more rapidly in alkaline, and still more rapidly in acid solution, the indicator should not be added until one is ready to titrate. The acid quinoid form of the compound is dichroic, showing a red-violet in thick layers and blue in thin. At a pH of 5.4 the indicator appears a neutral gray color by daylight or a pale red under tungsten light. The change to yellow is easily recognized in either case. Cf. Scanlan and Reid, Ind. Eng. Chem., Anal. Ed. 7:125 (1935). Bertrand’s reagents (glucose estimation): (a) 40 g of copper sulfate diluted to 1 liter; (b) rochelle salt 200 g, NaOH 150 g, and sufficient water to make 1 liter; (c) ferric sulfate 50 g, H2SO4 200 g, and sufficient water to make 1 liter; (d) KMnO4 5 g and sufficient water to make 1 liter. Bial’s reagent (for pentoses): dissolve 1 g of orcinol in 500 mL of 30% HCl to which 30 drops of a 10% ferric chloride solution have been added. Bismuth chloride, BiCl3 90.5N: 52 g per liter, using 1 : 5 HCl in place of water. Bismuth nitrate, Bi(N2O3)3 · 5H2O90.25N: 40 g per liter, using 1 : 5 HNO3 in place of water. Bismuth standard solution (quantitative color test for Bi): dissolve 1 g of bismuth in a mixture of 3 mL of concentrated HNO3 and 2.8 mL of H2O and make up to 100 mL with glycerol. Also dissolve 5 g of KI in 5 mL of water and make up to 100 mL with glycerol. The two solutions are used together in the colorimetric estimation of Bi. Boutron-Boudet solution: see soap solution.

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Bromchlorophenol blue, dibromodichlorophenol-sulfonphthalein (indicator): dissolve 0.1 g in 8.6 mL 0.02 N NaOH and dilute with water to 250 mL; pH range yellow 3.2–4.8 blue.

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Bromcresol green, tetrabromo-m-cresol-sulfonphthalein (indicator): dissolve 0.1 g in 7.15 mL 0.02 N NaOH and dilute with water to 250 mL; or, 0.1 g in 100 mL 20% alcohol; pH range yellow 4.0– 5.6 blue. Bromcresol purple, dibromo-o-cresol-sulfonphthalein (indicator): dissolve 0.1 g in 9.5 mL 0.02 N NaOH and dilute with water to 250 mL; or, 0.1 g in 100 mL 20% alcohol; pH range yellow 5.2– 6.8 purple. Bromine water, saturated solution: to 400 mL water add 20 mL of bromine; use a glass stopper coated with petrolatum. Bromphenol blue, tetrabromophenol-sulfonphthalein (indicator): dissolve 0.1 g in 7.45 mL 0.02 N NaOH and dilute with water to 250 mL; or, 0.1 g in 100 mL 20% alcohol; pH range yellow 3.6– 4.6 violet-blue. Bromphenol red, dibromophenol-sulfonphthalein (indicator): dissolve 0.1 g in 9.75 mL 0.02 N NaOH and dilute with water to 250 mL; pH range yellow 5.2–7.0 red. Bromthymol blue, dibromothymol-sulfonphthalein (indicator): dissolve 0.1 g in 8.0 mL 0.02 N NaOH and dilute with water to 250 mL; or, 0.1 g in 100 mL of 20% alcohol; pH range yellow 6.0– 7.6 blue. Brucke’s reagent (protein precipitant): dissolve 50 g of KI in 500 mL of water, saturate with HgI2 (about 120 g), and dilute to 1 liter. Cadmium chloride, CdCl2 90.5N: 46 g per liter. Cadmium nitrate, Cd(NO3)2 · 4H2O9 0.5N: 77 g per liter. Cadmium sulfate, CdSO4 · 4H2O9 0.5N: 70 g per liter. Calcium chloride, CaCl2 · 6H2O9 0.5N: 55 g per liter. Calcium hydroxide, Ca(OH)2 90.04N: 10 g per liter for saturation. Calcium nitrate, Ca(NO3)2 · 4H2O90.5N: 59 g per liter. Calcium sulfate, CaSO4 · 2H2O90.03N: mechanically stir 10 g in a liter of water for 3 hours; decant and use the clear liquid. Carbon disulfide, CS2 : commercial grade which is colorless. Chloride reagent: dissolve 1.7 g of AgNO3 and 25 g KNO3 in water, add 17 mL of concentrated NH4OH and make up to 1 liter with water. Chlorine water, saturated solution: pass chlorine gas into small amounts of water as needed; solutions deteriorate on standing. Chloroform, CHCl3 : commercial grade. Chloroplatinic acid, H2PtCl6 · 6H2O910% solution: dissolve 1 g in 9 mL of water; keep in a dropping bottle. Chlorphenol red, dichlorophenol-sulfonphthalein (indicator): dissolve 0.1 g in 11.8 mL 0.02 N NaOH and dilute with water to 250 mL; or, 0.1 g in 100 mL 20% alcohol; pH range yellow 5.2– 6.6 red. Chromic chloride, CrCl3 90.5N: 26 g per liter. Chromic nitrate, Cr(NO3)3 90.5N: 40 g per liter. Chromic sulfate, Cr2(SO4)3 · 18H2O9 0.5N: 60 g per liter. Cobaltous nitrate, Co(NO3)2 · 6H2O9 0.5N: 73 g per liter.

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Cobaltous sulfate, CoSO4 · 7H2O9 0.5N: 70 g per liter.

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Cochineal (indicator): triturate 1 g with 75 mL alcohol and 75 mL water, let stand for two days and filter; pH range red 4.8– 6.2 violet. Congo red, sodium tetrazodiphenyl-naphthionate (indicator): dissolve 0.1 g in 100 mL water; pH range blue 3.0– 5.2 red. Corallin (indicator): see rosolic acid. Cresol red, o-cresol-sulfonphthalein (indicator): dissolve 0.1 g in 13.1 mL 0.02N NaOH and dilute with water to 250 mL; or, 0.1 g in 100 mL 20% alcohol; pH range yellow 7.2–8.8 red. o-Cresolphthalein (indicator): dissolve 0.1 g in 250 mL alcohol; pH range colorless 8.2–10.4 red. Cupferron (iron analysis): dissolve 6 g of ammonium nitrosophenyl-hydroxylamine (cupferron) in water and dilute to 100 mL. This solution is stable for about one week if protected from light. Cupric chloride, CuCl2 · 2H2O9 0.5N: 43 g per liter. Cupric nitrate, Cu(NO3)2 · 6H2O90.5N: 74 g per liter. Cupric sulfate, CuSO4 · 5H2O90.5N: 62 g per liter. Cuprous chloride, CuCl9 0.5N: 50 g per liter, using 1 : 5 HCl in place of water. Cuprous chloride, acid (for gas analysis, absorption of CO): cover the bottom of a 2-liter bottle with a layer of copper oxide 3⁄8 inch deep, and place a bundle of copper wire an inch thick in the bottle so that it extends from the top to the bottom. Fill the bottle with HCl (sp. gr. 1.10). The bottle is shaken occasionally, and when the solution is colorless or nearly so, it is poured into half-liter bottles containing copper wire. The large bottle may be filled with hydrochloric acid, and by adding the oxide or wire when either is exhausted, a constant supply of the reagent is available. Cuprous chloride, ammoniacal: this solution is used for the same purpose and is made in the same manner as the acid cuprous chloride above, except that the acid solution is treated with ammonia until a faint odor of ammonia is perceptible. Copper wire should be kept with the solution as in the acid reagent. Curcumin (indicator): prepare a saturated aqueous solution; pH range yellow 6.0–8.0 brownish red. Dibromophenol-tetrabromophenol-sulfonphthalein (indicator): dissolve 0.1 g in 1.21 mL 0.1N NaOH and dilute with water to 250 mL; pH range yellow 5.6–7.2 purple. Dimethyl glyoxime, (CH3CNOH)2 90.01N: 6 g in 500 mL of 95% alcohol. 2,4-Dinitrophenol (indicator): dissolve 0.1 g in a few mL alcohol, then dilute with water to 100 mL; pH range colorless 2.6– 4.0 yellow. 2,5-Dinitrophenol (indicator): dissolve 0.1 g in 20 mL alcohol, then dilute with water to 100 mL; pH range colorless 4– 5.8 yellow. 2,6-Dinitrophenol (indicator): dissolve 0.1 g in a few mL alcohol, then dilute with water to 100 mL; pH range colorless 2.4– 4.0 yellow. Esbach’s reagent (estimation of proteins): dissolve 10 g of picric acid and 20 g of citric acid in water and dilute to 1 liter. Eschka’s mixture (sulfur in coal): mix 2 parts of porous calcined MgO with 1 part of anhydrous Na2CO3 ; not a solution but a dry mixture. Ether, (C2H5)2O9use commercial grade.

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p-Ethoxychrysoidine, p-ethoxybenzeneazo-m-phenylenediamine (indicator): dissolve 0.1 g of the base in 100 mL 90% alcohol; or, 0.1 g of the hydrochloride salt in 100 mL water; pH range red 3.5– 5.5 yellow.

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Ethyl bis-(2,4-dinitrophenyl) acetate (indicator): the stock solution is prepared by saturating a solution containing equal volumes of alcohol and acetone with the indicator; pH range colorless 7.4– 9.1 deep blue. This compound is available commercially. The preparation of this compound is described by Fehnel and Amstutz, Ind. Eng. Chem., Anal. Ed. 16:53 (1944), and by von Richter, Ber. 21:2470 (1888), who recommended it for the titration of orange- and red-colored solutions or dark oils in which the endpoint of phenol-phthalein is not easily visible. The indicator is an orange solid which after crystallization from benzene gives pale yellow crystals melting at 150– 153.5⬚C, uncorrected. Fehling’s solution (sugar detection and estimation): (a) Copper sulfate solution: dissolve 34.639 g of CuSO4 · 5H2O in water and dilute to 500 mL. (b) Alkaline tartrate solution: dissolve 173 g of rochelle salts (KNaC4O6 · 4H2 O) and 125 g of KOH in water and dilute to 500 mL. Equal volumes of the two solutions are mixed just prior to use. The Methods of the Assoc. of Official Agricultural Chemists give 50 g of NaOH in place of the 125 g KOH. Ferric chloride, FeCl3 90.5N: 27 g per liter. Ferric nitrate, Fe(NO3)3 · 9H2O9 0.5N: 67 g per liter. Ferrous ammonium sulfate, Mohr’s salt, FeSO4 · (NH4)2SO4 · 6H2O9 0.5N: 196 g per liter. Ferrous sulfate, FeSO4 · 7H2O90.5N: 80 g per liter; add a few drops of H2SO4 . Folin’s mixture (for uric acid): dissolve 500 g of ammonium sulfate, 5 g of uranium acetate, and 6 mL of glacial acetic acid, in 650 mL of water. The volume is about a liter. Formal or Formalin: use the commercial 40% solution of formaldehyde. Froehde’s reagent (gives characteristic colorations with certain alkaloids and glycosides): dissolve 0.01 g of sodium molybdate in 1 mL of concentrated H2SO4 ; use only a freshly prepared solution. Gallein (indicator): dissolve 0.1 g in 100 mL alcohol; pH range light brown-yellow 3.8–6.6 rose. Glyoxylic acid solution (protein detection): cover 10 g of magnesium powder with water and slowly add 250 mL of a saturated oxalic solution, keeping the mixture cool; filter off the magnesium oxalate, acidify the filtrate with acetic acid and make up to a liter with water. Guaiacum tincture: dissolve 1 g of guaiacum in 100 mL of alcohol. Gunzberg’s reagent (detection of HCl in gastric juice): dissolve 4 g of phloroglucinol and 2 g of vanillin in 100 mL of absolute alcohol; use only a freshly prepared solution. Hager’s reagent (for alkaloids): this reagent is a saturated solution of picric acid in water. Hanus solution (for determination of iodine number): dissolve 13.2 g of iodine in a liter of glacial acetic acid that will not reduce chromic acid; add sufficient bromine to double the halogen content determined by titration (3 mL is about the right amount). The iodine may be dissolved with the aid of heat, but the solution must be cold when the bromine is added. Hematoxylin (indicator): dissolve 0.5 g in 100 mL alcohol; pH range yellow 5.0–6.0. Heptamethoxy red, 2,4,6,2⬘,4⬘,2⬙,4⬙-heptamethoxytriphenyl carbinol (indicator): dissolve 0.1 g in 100 mL alcohol; pH range red 5.0–7.0 colorless. Hydriodic acid, HI90.5N: 64 g per liter. Hydrobromic acid, HBr9 0.5N: 40 g per liter. Hydrochloric acid, HCl9 5N: 182 g per liter; sp. gr. 1.084.

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Hydrofluoric acid, H2F2 948% solution: use as purchased, and keep in the special container.

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Hydrogen peroxide, H2O2 93% solution: use as purchased. Hydrogen sulfide, H2S: prepare a saturated aqueous solution. Indicator solutions: a number of indicator solutions are listed in this section under the names of the indicators; e.g., alizarin, aurin, azolitmin, et al., which follow alphabetically. See also various index entries. Indigo carmine, sodium indigodisulfonate (indicator): dissolve 0.25 g in 100 mL 50% alcohol; pH range blue 11.6– 14.0 yellow. Indo-oxine, 5,8-quinolinequinone-8-hydroxy-5-quinoyl-5-imide (indicator): dissolve 0.05 g in 100 mL alcohol; pH range red 6.0– 8.0 blue. Cf. Berg and Becker, Z. Anal. Chem. 119:81 (1940). Iodeosin, tetraiodofluorescein (indicator): dissolve 0.1 g in 100 mL ether saturated with water; pH range yellow 0– about 4 rose-red; see also under methyl orange. Iodic acid, HIO3 90.5N (HIO3/12): 15 g per liter. Iodine: see tincture of iodine. Lacmoid (indicator): dissolve 0.5 g in 100 mL alcohol; pH range red 4.4–6.2 blue. Lead acetate, Pb(C2H3O2)2 · 3H2O9 0.5N: 95 g per liter. Lead chloride, PbCl2 9saturated solution is 1/7N. Lead nitrate, Pb(NO3)2 9 0.5N: 83 g per liter. Lime water: see calcium hydroxide. Litmus (indicator): powder the litmus and make up a 2% solution in water by boiling for 5 minutes; pH range red 4.5– 8.3 blue. Magnesia mixture: 100 g of MgSO4 , 200 g of NH4Cl, 400 mL of NH4Cl, 800 mL of water; each mL # 0.01 g phosphorus (P). Magnesium chloride, MgCl2 · 6H2O90.5N: 50 g per liter. Magnesium nitrate, Mg(NO3)2 · 6H2O9 0.5N: 64 g per liter. Magnesium sulfate, epsom salts, MgSO4 · 7H2O9 0.5N: 62 g per liter; saturated solution dissolve 600 g of the salt in water and dilute to 1 liter. Manganous chloride, MnCl2 · 4H2O90.5N: 50 g per liter. Manganous nitrate, Mn(NO3)2 · 6H2O9 0.5N: 72 g per liter. Manganous sulfate, MnSO4 · 7H2O90.5N: 69 g per liter. Marme’s reagent (gives yellowish-white precipitate with salts of alkaloids): saturate a boiling solution of 4 parts of KI in 12 parts of water with CdI2 ; then add an equal volume of cold saturated KI solution. Marquis reagent (gives a purple-red coloration, then violet, then blue with morphine, codeine, dionine, and heroine): mix 3 mL of concentrated H2SO4 with 3 drops of a 35% formaldehyde solution. Mayer’s reagent (gives white precipitate with most alkaloids in a slightly acid solution): dissolve 13.55 g of HgCl2 and 50 g of KI in a liter of water. Mercuric chloride, HgCl2 90.5N: 68 g per liter. Mercuric nitrate, Hg(NO3)2 9 0.5N: 81 g per liter. Mercuric sulfate, HgSO4 9 0.5N: 74 g per liter.

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Mercurous nitrate, HgNO3 : mix 1 part of HgNO3 , 20 parts of H2O, and 1 part of HNO3 .

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Metacresol purple, m-cresol-sulfonphthalein (indicator): dissolve 0.1 g in 13.6 mL 0.02N NaOH and dilute with water to 250 mL; acid pH range red 0.5–2.5 yellow, alkaline pH range yellow 7.4– 9.0 purple. Metanil yellow, diphenylaminoazo-m-benzene sulfonic acid (indicator): dissolve 0.25 g in 100 mL alcohol; pH range red 1.2–2.3 yellow. Methyl green, hexamethylpararosaniline hydroxymethylate (component of mixed indicator): dissolve 0.1 g in 100 mL alcohol; when used with equal parts of hexamethoxytriphenyl carbinol gives color change from violet to green at a titration exponent (pI) of 4.0. Methyl orange, orange III, tropeolin D, sodium p-dimethylaminoazobenzenesulfonate (indicator): dissolve 0.1 g in 100 mL water; pH range red 3.0–4.4 orange-yellow. If during a titration where methyl yellow is being used a precipitate forms which tends to remove the indicator from the aqueous phase, methyl orange will be found to be a more suitable indicator. This occurs, for example, in titrations of soaps with acids. The fatty acids, liberated by the titration, extract the methyl yellow so that the endpoint cannot be perceived. Likewise methyl orange is more suitable for titrations in the presence of immiscible organic solvents such as carbon tetrachloride or ether used in the extraction of alkaloids for analysis. Iodeosin (q.v.) has also been proposed as an indicator for such cases. Cf. Mylius and Foerster, Ber. 24:1482 (1891); Z. Anal. Chem. 31:240 (1892). Methyl red, p-dimethylaminoazobenzene-o⬘-carboxylic acid (indicator): dissolve 0.1 g in 18.6 mL of 0.02N NaOH and dilute with water to 250 mL; or, 0.1 g in 60% alcohol; pH range red 4.4– 6.2 yellow. Methyl violet (indicator): dissolve 0.25 g in 100 mL water, pH range blue 1.5–3.2 violet. Methyl yellow, p-dimethylaminoazobenzene, benzeneazodimethylaniline (indicator): dissolve 0.1 g in 200 mL alcohol; pH range red 2.9–4.0 yellow. The color change from yellow to orange can be perceived somewhat more sharply than the change of methyl orange from orange to rose, so that methyl yellow seems to deserve preference in many cases. See also under methyl orange. Methylene blue, N,N,N⬘,N⬘-tetramethylthionine (component of mixed indicator): dissolve 0.1 g in 100 mL alcohol; when used with equal part of methyl yellow gives color change from blue-violet to green at a titration exponent (pI) of 3.25; when used with equal part of 0.2% methyl red in alcohol gives color change from red-violet to green at a titration exponent (pI) of 5.4; when used with an equal part of neutral red gives color change from violet-blue to green at a titration exponent (pI) of 7.0. Millon’s reagent (gives a red precipitate with certain proteins and with various phenols): dissolve 1 part of mercury in 1 part of HNO3 (sp. gr. 1.40) with gentle heating, then add 2 parts of water; a few crystals of KNO3 help to maintain the strength of the reagent. Mohr’s salt: see ferrous ammonium sulfate.

␣-Naphthol solution: dissolve 144 g of ␣-naphthol in enough alcohol to make a liter of solution. ␣-Naphtholbenzein (indicator): dissolve 0.1 g in 100 mL 70% alcohol; pH range colorless 9.0– 11.0 blue. ␣-Naphtholphthalein (indicator): dissolve 0.1 g in 50 mL alcohol and dilute with water to 100 mL; pH range pale yellow-red 7.3–8.7 green. Nessler’s reagent (for free ammonia): dissolve 50 g of KI in the least possible amount of cold water; add a saturated solution of HgCl2 until a very slight excess is indicated; add 400 mL of a 50% solution of KOH; allow to settle, make up to a liter with water, and decant.

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Neutral red, toluylene red, dimethyldiaminophenazine chloride, aminodimethylaminotoluphenazine hydrochloride (indicator): dissolve 0.1 g in 60 mL alcohol and dilute with water to 100 mL; pH range red 6.8– 8.0 yellow-orange.

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Nickel chloride, NiCl2 · 6H2O90.5N: 59 g per liter. Nickel nitrate, Ni(NO3)2 · 6H2O90.5N: 73 g per liter. Nickel sulfate, NiSO4 · 6H2O90.5N: 66 g per liter. Nitramine, picrylmethylnitramine, 2,4,6-trinitrophenylmethyl nitramine (indicator): dissolve 0.1 g in 60 mL alcohol and dilute with water to 100 mL; pH range colorless 10.8–13.0 redbrown; the solution should be kept in the dark as nitramine is unstable; on boiling with alkali it decomposes quickly. Fresh solutions should be prepared every few months. Nitric acid, HNO3 9 5N: 315 g per liter; sp. gr. 1.165. Nitrohydrochloric acid: see aqua regia. p-Nitrophenol (indicator): dissolve 0.2 g in 100 mL water; pH range colorless at about 5–7 yellow. Nitroso-␤-naphthol, HOC10H6NO9saturated solution: saturate 100 mL of 50% acetic acid with the solid. Nylander’s solution (detection of glucose): dissolve 40 g of rochelle salt and 20 g of bismuth subnitrate in 1000 mL of an 8% NaOH solution. Obermayer’s reagent (detection of indoxyl in urine): dissolve 4 g of FeCl3 in a liter of concentrated HCl. Orange III (indicator): see under methyl orange. Oxalic acid, H2C2O4 · 2H2O: dissolve in ten parts of water. Pavy’s solution (estimation of glucose): mix 120 mL of Fehling’s solution and 300 mL of ammonium hydroxide (sp. gr. 0.88), and dilute to a liter with water. Perchloric acid, HClO4 960%: use as purchased. Phenol red, phenol-sulfonphthalein (indicator): dissolve 0.1 g in 14.20 mL 0.02N NaOH and dilute with water to 250 mL; or, 0.1 g in 100 mL 20% alcohol; pH range yellow 6.8–8.0 red. Phenol solution: dissolve 20 g of phenol (carbolic acid) in a liter of water. Phenol sulfonic acid (determination of nitrogen as nitrate; water analysis for nitrate): dissolve 25 g pure, white phenol in 150 mL of pure concentrated H2SO4 , add 75 mL of fuming H2SO4 (15% SO3), stir well and heat for two hours at 100⬚C. Phenolphthalein (indicator): dissolve 1 g in 60 mL of alcohol and dilute with water to 100 mL; pH range colorless 8.2– 10.0 red. Phosphoric acid, ortho, H3PO4 90.5N: 16 g per liter. Poirrer blue C4B (indicator): dissolve 0.2 g in 100 mL water; pH range blue 11.0–13.0 red. Potassium acid antimonate, KH2SbO4 9 0.1N: boil 23 g of the salt with 950 mL of water for 5 minutes, cool rapidly and add 35 mL of 6N KOH; allow to stand for one day, filter dilute filtrate to a liter. Potassium arsenate, K3AsO4 90.5N (K3AsO4/10): 26 g per liter. Potassium arsenite, KAsO2 90.5N (KAsO2/6): 24 g per liter. Potassium bromate, KBrO3 90.5N (KBrO3/12): 14 g per liter. Potassium bromide, KBr9 0.5N: 60 g per liter.

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Potassium carbonate, K2CO3 93N: 207 g per liter.

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Potassium chloride, KCl9 0.5N: 37 g per liter. Potassium chromate, K2CrO4 90.5N: 49 g per liter. Potassium cyanide, KCN9 0.5N: 33 g per liter. Potassium dichromate, K2Cr2O7 9 0.5N (K2Cr2O7/8): 38 g per liter. Potassium ferricyanide, K3Fe(CN)6 90.5N: 55 g per liter. Potassium ferrocyanide, K4Fe(CN)6 · 3H2O 90.5N: 53 g per liter. Potassium hydroxide, KOH95N: 312 g per liter. Potassium iodate, KIO3 90.5N (KIO3/12): 18 g per liter. Potassium iodide, KI90.5N: 83 g per liter. Potassium nitrate, KNO3 9 0.5N: 50 g per liter. Potassium nitrate, KNO2 9 6N: 510 g per liter. Potassium permanganate, KMnO4 90.5N (KMnO4/10): 16 g per liter. Potassium pyrogallate (oxygen in gas analysis): weigh out 5 g of pyrogallol (pyrogallic acid), and pour upon it 100 mL of a KOH solution. If the gas contains less than 28% of oxygen, the KOH solution should be 500 g KOH in a liter of water; if there is more than 28% of oxygen in the gas, the KOH solution should be 120 g of KOH in 100 mL of water. Potassium sulfate, K2SO4 9 0.5N: 44 g per liter. Potassium thiocyanate, KCNS 9 0.5N: 49 g per liter. Precipitating reagent (for group II, anions): dissolve 61 g of BaCl2 · 2H2O and 52 g of CaCl2 · 6H2O in water and dilute to 1 liter. If the solution becomes turbid, filter and use filtrate. Quinaldine red (indicator): dissolve 0.1 g in 100 mL alcohol; pH range colorless 1.4–3.2 red. Quinoline blue, cyanin (indicator): dissolve 1 g in 100 mL alcohol; pH range colorless 6.6–8.6 blue. Rosolic acid, aurin, corallin, corallinphthalein, 4,4⬘-dihydroxy-fuchsone, 4,4⬘-dihydroxy-3methyl-fuchsone (indicator): dissolve 0.5 g in 50 mL alcohol and dilute with water to 100 mL. Salicyl yellow (indicator): see alizarin yellow GG. Scheibler’s reagent (precipitates alkaloids, albumoses and peptones): dissolve sodium tungstate in boiling water containing half its weight of phosphoric acid (sp. gr. 1.13); on evaporation of this solution, crystals of phosphotungstic acid are obtained. A 10% solution of phosphotungstic acid in water constitutes the reagent. Schweitzer’s reagent (dissolves cotton, linen, and silk, but not wool); add NH4Cl and NaOH to a solution of copper sulfate. The blue precipitate is filtered off, washed, pressed, and dissolved in ammonia (sp. gr. 0.92). Silver nitrate, AgNO3 90.25N: 43 g per liter. Silver sulfate, Ag2SO4 9N/13 (saturated solution): stir mechanically 10 g of the salt in a liter of water for 3 hours; decant and use the clear liquid. Soap solution (for hardness in water): (a) Clark’s or A.P.H.A. Stand. Methods— prepare stock solution of 100 g of pure powdered castile soap in a liter of 80% ethyl alcohol; allow to stand over night and decant. Titrate against CaCl2 solution (0.5 g CaCO3 dissolved in a concentrated HCl, neutralized with NH4OH to slight alkalinity using litmus as the indicator, make up to 500 mL; 1 mL of this solution is equivalent to 1 mg CaCO3) and dilute with 80% alcohol until 1 mL of the resulting solution is equivalent to 1 mL of the standard CaCl2 making due allowance

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for the lather factor (the lather factor is that amount of standard soap solution required to produce a permanent lather in a 50-mL portion of distilled water). One milliliter of this solution after subtracting the lather factor is equivalent to 1 mg of CaCO3 . (b) Boutron-Boudet— dissolve 100 g of pure castile soap in about 2500 mL of 56% ethyl alcohol and adjust so that 2.4 mL will give a permanent lather with 40 mL of a solution containing 0.59 g Ba(NO3)2 per liter of water; 2.4 mL of this solution is equivalent to 22 French degrees or 220 parts per million of hardness (as CaCO3) on a 40-mL sample of water.

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Sodium acetate, NaC2H3O2 · 3H2O: dissolve 1 part of the salt in 10 parts of water. Sodium acetate, acid: dissolve 100 g of sodium acetate and 30 mL of glacial acetic acid in water and dilute to 1 liter. Sodium bismuthate (oxidation of manganese): heat 20 parts of NaOH nearly to redness in an iron or nickel crucible, and add slowly 10 parts of basic bismuth nitrate which has been previously dried. Add 2 parts of sodium peroxide, and pour the brownish-yellow fused mass on an iron plate to cool. When cold break up in a mortar, extract with water, and collect on an asbestos filter. Sodium carbonate, Na2CO3 93N: 159 g per liter; one part Na2CO3 , or 2.7 parts of the crystalline Na2CO3 · 10H2O in 5 parts of water. Sodium chloride, NaCl90.5N: 29 g per liter. Sodium chloroplatinite, Na2PtCl4 : dissolve 1 part of the salt in 12 parts of water. Sodium cobaltinitrite, Na2Co(NO2)6 90.3N: dissolve 230 g of NaNO2 in 500 mL of water, add 160 mL of 6N acetic acid and 35 g of Co(NO3)2 · 6H2 O. Allow to stand one day, filter, and dilute the filtrate to a liter. Sodium hydrogen phosphate, Na2HPO4 · 12H2O90.5N: 60 g liter. Sodium hydroxide, NaOH9 5N: 220 g per liter. Sodium hydroxide, alcoholic: dissolve 20 g of NaOH in alcohol and dilute to 1 liter with alcohol. Sodium hypobromite: dissolve 100 g of NaOH in 250 mL of water and add 25 mL of bromine. Sodium nitrate, NaNO3 90.5N: 43 g per liter. Sodium nitroprusside (for sulfur detection): dissolve about 1 g of sodium nitroprusside in 10 mL of water; as the solution deteriorates on standing, only freshly prepared solutions should be used. This compound is also called sodium nitroferricyanide and has the formula Na2Fe(NO)(CN)5 · 2H2 O. Sodium polysulfide, Na2Sx : dissolve 480 g of Na2S · 9H2O in 500 mL of water, add 40 g of NaOH and 18 g of sulfur, stir mechanically and dilute to 1 liter with water. Sodium sulfate, Na2SO4 90.5N: 35 g per liter. Sodium sulfide, Na2S: saturate NaOH solution with H2S, then add as much NaOH as was used in the original solution. Sodium sulfite, Na2SO3 · 7H2O90.5N: 63 g per liter. Sodium sulfite, acid (saturated): dissolve 600 g of NaHSO3 in water and dilute to 1 liter; for the preparation of addition compounds with aldehydes and ketones: prepare a saturated solution of sodium carbonate in water and saturate with sulfur dioxide. Sodium tartrate, acid, NaHC4H4O6 : dissolve 1 part of the salt in 10 parts of water. Sodium thiosulfate, Na2S2O3 · 5H2O: one part of the salt in 40 parts of water. Sonnenschein’s reagent (alkaloid detection): a nitric acid solution of ammonium molybdate is treated with phosphoric acid. The precipitate so produced is washed and boiled with aqua regia

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until the ammonium salt is decomposed. The solution is evaporated to dryness and the residue is dissolved in 10% HNO3 .

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Stannic chloride, SnCl4 9 0.5N: 33 g per liter. Stannous chloride, SnCl2 · 2H2O90.5N: 56 g per liter. The water should be acid with HCl and some metallic tin should be kept in the bottle. Starch solution (iodine indicator): dissolve 5 g of soluble starch in cold water, pour the solution into 2 liters of water and boil for a few minutes. Keep in a glass-stoppered bottle. Starch solution (other than soluble): make a thin paste of the starch with cold water, then stir in 200 times its weight of boiling water and boil for a few minutes. A few drops of chloroform added to the solution acts as a preservative. Stoke’s reagent: dissolve 30 g of ferrous sulfate and 20 g of tartaric acid in water and dilute to 1 liter. When required for use, add strong ammonia until the precipitate first formed is dissolved. Strontium chloride, SrCl2 · 6H2O90.5N: 67 g per liter. Strontium nitrate, Sr(NO3)2 9 0.5N: 53 g per liter. Strontium sulfate, SrSO4 : prepare a saturated solution. Sulfanilic acid (for detection of nitrites): dissolve 8 g of sulfanilic acid in 1 liter of acetic acid (sp. gr. 1.04). Sulfuric acid, H2SO4 95N: 245 g per liter, sp. gr. 1.153. Sulfurous acid, H2SO3 : saturate water with sulfur dioxide. Tannic acid: dissolve 1 g tannic acid in 1 mL alcohol and make up to 10 mL with water. Tartaric acid, H2C4H4O6 : dissolve one part of the acid in 3 parts of water; for a saturated solution dissolve 750 g of tartaric acid in water and dilute to 1 liter. Tetrabromophenol blue, tetrabromophenol-tetrabromosulfonphthalein (indicator): dissolve 0.1 g in 5 mL 0.02N NaOH and dilute with water to 250 mL; pH range yellow 3.0–4.6 blue. Thymol blue, thymol-sulfonphthalein (indicator): dissolve 0.1 g in 10.75 mL 0.02N NaOH and dilute with water to 250 mL; or dissolve 0.1 g in 20 mL warm alcohol and dilute with water to 100 mL; pH range (acid) red 1.2–2.8 yellow, and (alkaline) yellow 8.0–9.6 blue. Thymolphthalein (indicator): dissolve 0.1 g in 100 mL alcohol; pH range colorless 9.3–10.5 blue. Tincture of iodine (antiseptic): add 70 g of iodine and 50 g of KI to 50 mL of water; make up to 1 liter with alcohol. o-Tolidine solution (for residual chlorine in water analysis): dissolve 1 g of pulverized o-tolidine, m.p. 129⬚C., in 1 liter of dilute hydrochloric acid (100 mL conc. HCl diluted to 1 liter). Toluylene red (indicator): see neutral red. Trichloroacetic acid: dissolve 100 g of the acid in water and dilute to 1 liter. Trinitrobenzene, 1,3,5-trinitrobenzene (indicator): dissolve 0.1 g in 100 mL alcohol; pH range colorless 11.5– 14.0 orange. Trinitrobenzoic acid, 2,4,6-trinitrobenzoic acid (indicator): dissolve 0.1 g in 100 mL water; pH range colorless 12.0– 13.4 orange-red. Tropeolin D (indicator): see methyl orange. Tropeolin O, sodium 2,4-dihydroxyazobenzene-4-sulfonate (indicator): dissolve 0.1 g in 100 mL water; pH range yellow 11.0–13.0 orange-brown.

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Tropeolin OO, orange IV, sodium p-diphenylamino-azobenzene sulfonate, sodium 4⬘-anilinoazobenzene-4-sulfonate (indicator): dissolve 0.1 g in 100 mL water; pH range red 1.3–3.2 yellow.

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Tropeolin OOO, sodium ␣-naphtholazobenzene sulfonate (indicator): dissolve 0.1 g in 100 mL water; pH range yellow 7.6– 8.9 red. Turmeric paper (gives a rose-brown coloration with boric acid): wash the ground root of turmeric with water and discard the washings. Digest with alcohol and filter, using the clear filtrate to impregnate white, unsized paper, which is then dried. Uffelmann’s reagent (gives a yellow coloration in the presence of lactic acid): add a ferric chloride solution to a 2% phenol solution until the solution becomes violet in color. Wagner’s solution (phosphate rock analysis): dissolve 25 g citric acid and 1 g salicylic acid in water, and make up to 1 liter. Twenty-five to fifty milliliters of this reagent prevents precipitation of iron and aluminum. Wijs solution (for iodine number): dissolve 13 g resublimed iodine in 1 liter of glacial acetic acid (99.5%), and pass in washed and dried (over or through H2SO4) chlorine gas until the original thio titration of the solution is not quite doubled. There should be only a slight excess of iodine and no excess of chlorine. Preserve the solution in amber colored bottles sealed with paraffin. Do not use the solution after it has been prepared for more than 30 days. Xylene cyanole-methyl orange indicator, Schoepfle modification (for partially color blind operators): dissolve 0.75 g xylene cyanole FF (Eastman No. T 1579) and 1.50 g methyl orange in 1 liter of water. p-Xylenol blue, 1,4-dimethyl-5-hydroxybenzene-sulfonphthalein (indicator): dissolve 0.1 g in 250 mL alcohol; pH range (acid) red 1.2–2.8 yellow, and (alkaline) yellow 8.0–9.6 blue. Zinc chloride, ZnCl2 9 0.5N: 34 g per liter. Zinc nitrate, Zn(NO3)2 · 6H2O9 0.5N: 74 g per liter. Zinc sulfate, ZnSO4 · 7H2O9 0.5N: 72 g per liter.

TABLE 11.49 TLV Concentration Limits for Gases and Vapors Exposure limits (threshold limit value or TLV) are those set by the Occupational Safety and Health Administration and represent conditions to which most workers can be exposed without adverse effects. The TLV value is expressed as a time weighted average airborne concentration over a normal 8-hour workday and 40-hour workweek. Maximum allowable exposure Substance Acetaldehyde Acetic acid Acetic anhydride Acetone Acetonitrile Acetophenone Acetylene Acrolein

ppm 25 10 5 750 40 10

mg · m⫺3 45 25 21 1780 67 49

Toxicity carcinogen

slightly narcotic 0.1

0.23

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TABLE 11.49 TLV Concentration Limits for Gases and Vapors (Continued) Maximum allowable exposure Substance Acrylic acid Acrylonitrile Acrylonitrile Allyl alcohol Allyl chloride Allyl glycidyl ether Ammonia Aniline Arsine Benzene Benzenethiol p-Benzoquinone Benzoyl chloride Benzoyl peroxide Benzyl acetate Benzyl chloride Biphenyl Bis(2-aminoethyl)amine Bis(2-chloroethyl) ether Bis(2-chloromethyl) ether Bis(2-ethylhexyl) phthalate Boron tribromide Boron trichloride Boron trifluoride Bromine Bromine pentafluoride Bromine trifluoride Bromochloromethane (Halon 1011) Bromoethane Bromoethylene Bromoform Bromomethane 1,3-Butadiene Butane 1-Butanethiol 1-Butanol 2-Butanol 2-Butanone 2-Butoxyethanol Butyl acetate sec-Butyl acetate tert-Butyl acetate Butyl acrylate tert-Butyl alcohol Butylamine tert-Butyl chromate (as CrO3) Butyl glycidyl ether

ppm

mg · m⫺3

2 2 20 2 1 5 25 2 0.05 10 0.5 0.1 0.5

5.9 4.3 45 4.8 3 22 18 7.6 0.2 32 2.3

Toxicity

toxic carcinogen highly toxic carcinogen

5 10 1 0.2 1 5 0.001

carcinogen

29 carcinogen 5

1 1 0.1 0.1 200 5 5 0.5 5

3 0.7

highly toxic highly toxic 1060 22 22 5 19

2 800 0.5 50 100 200 25 150 200 200 10 100 5 50

toxic highly toxic

1900 1.8 152 303 590 121 710 950 950 300 15 0.1 270

carcinogen slightly toxic highly toxic, carcinogen slightly anesthetic, carcinogen slightly anesthetic

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TABLE 11.49 TLV Concentration Limits for Gases and Vapors (Continued) Maximum allowable exposure Substance Butyl mercaptan p-tert-Butyltoluene (⫹)-Camphor Caprolactam Carbon dioxide Carbon disulfide Carbon monoxide Carbon tetrachloride Carbonyl chloride Carbonyl fluoride Chlordane Chlorine Chlorine dioxide Chlorine trifluoride Chloroacetaldehyde ␣-Chloroacetophenone Chloroacetyl chloride Chlorobenzene 2-Chloro-1,3-butadiene Chlorodifluoromethane (CFC 22) Chloroethane 2-Chloroethanol Chloroethylene (vinyl chloride) Chloroform (trichloromethane) Chloromethane 1-Chloro-1-nitropropane Chloropentafluoroethane (CFC 115) 3-Chloro-1-propene (allyl chloride) o-Chlorotoluene Chlorotrifluoroethylene Chromyl chloride (CrO2Cl2) o-Cresol (also m-, p-) trans-Crotonaldehyde Cyanogen Cyanogen chloride Cyclohexane Cyclohexanol Cyclohexanone Cyclohexene Cyclohexylamine 1,3-Cyclopentadiene Cyclopentane Cyclopropane 2,4-D DDT Decaborane Diacetone alcohol 2,2’-Diaminodiethylamine Diazomethane

ppm 0.5 10 2 5 5000 10 25 10 0.1 2 0.5 0.1 0.1 1 0.05 0.05 10 10 1000 100 1 5 10 50 20 1000 1 50 0.025 5 2 10 0.3 300 50 25 300 10 75 600

mg · m⫺3

Toxicity

1.5 12 9000 31 28 65

toxic

toxic 0.5 1.5 0.3 0.4 3 0.3

highly toxic highly toxic

46 carcinogen 3540 264 3.3 13 49 103 100 6320 3 259

low toxicity toxic, carcinogen toxic, carcinogen

carcinogen toxic carcinogen

22 5.7 20

highly toxic

1030 206 100 1015 41 1720 anesthetic

0.05 50 1 0.2

10 1 0.3 238 4.2 carcinogen

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TABLE 11.49 TLV Concentration Limits for Gases and Vapors (Continued) Maximum allowable exposure Substance

ppm

mg · m⫺3

Diborane Dibromodifluoromethane 1,2-Dibromoethane Dibutyl phthalate Dichloroacetylene o-Dichlorobenzene p-Dichlorobenzene Dichlorodifluoromethane (Freon 12) 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene Dichlorofluoromethane (Freon 21) Dichloromethane 1,1-Dichloro-1-nitroethane 1,2-Dichloropropane 1,3-Dichloropropene Dichlorosilane 1,2-Dichlorotetrafluoroethane (Freon 114) Dieldrin Diethanolamine Diethylamine Diethyl ether Diglycidyl ether Diisobutyl ketone Diisopropylamine Diiopropyl ether Dimethoxymethane N,N-Dimethylacetamide Dimethylamine N,N-Dimethylaniline Dimethyl 1,2-dibromo-2,2-dichloroethylphosphate Dimethyl ether

0.1 100

0.1 860

1-(1,1-Dimethylethyl)-4-methylbenzene N,N-Dimethylformamide 2,6-Dimethyl-4-heptanone 1,1-Dimethylhydrazine Dimethyl phthalate 2,2-Dimethylpropane Dimethyl sulfate Dinitrobenzene Dinitro-o-cresol Dinitrotoluene 1,4-Dioxane Diphenyl Diphenyl ether Dipropylene glycol methyl ether— skin

Toxicity

carcinogen 5 0.1 25 10 1000 100 10 5 200 200 10 50 10 75 1 1000 0.46 5 400 0.5 25 5 250 1000 10 5 5

150 60 4950 405 40 20 793 793 42 174 60 347

carcinogen

carcinogen carcinogen

carcinogen carcinogen carcinogen highly toxic

7000 0.25 15 1210 2.8 150 20 1040 3110 35 9.2 25 3

highly toxic

slightly toxic, anesthetic 1 10 25 0.5

0.1 0.15

25 0.2 1 100

6.1 30 1 5 0.5 1 0.2 1.5 90 1 7 600

carcinogen probably anesthetic carcinogen

carcinogen

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TABLE 11.49 TLV Concentration Limits for Gases and Vapors (Continued) Maximum allowable exposure Substance Endrin— skin Epichlorohydrin 2,3-Epoxy-1-propanol (glycidol) 1,2-Ethanediamine Ethanethiol Ethanol Ethanolamine 2-Ethoxyethanol (Cellosolve) 2-Ethoxyethyl acetate Ethyl acetate Ethyl acrylate Ethylamine Ethylbenzene Ethylene Ethylene glycol Ethylene glycol dinitrate Ethyleneimine Ethylene oxide Ethyl formate Ethyl mercaptan Ethyl silicate Fluorine Fluorotrichloromethane (Freon 11) Formaldehyde Formamide Formic acid 2-Furancarboxaldehyde (furfural) 2-Furanmethanol Glycerol Heptachlor Heptane 2-Heptanone 3-Heptanone Hexachloro-1,3-butadiene Hexachlorocyclohexane (lindane) Hexachloroethane Hexachloronaphthalene Hexamethylphosphoric triamide Hexane 2-Hexanone sec-Hexyl acetate Hexylene glycol Hydrazine Hydrogen bromide Hydrogen chloride Hydrogen cyanide Hydrogen fluoride Hydrogen iodide Hydrogen peroxide (90%)

ppm

2 50 10 0.5 1000 3 5 5 400 5 5 100

mg · m⫺3 0.1 7.6 150 25 1880 7.5 18 27 1400 20 9.2 435

Toxicity

carcinogen

highly toxic anesthetic

39 0.2 0.05 1 100 0.1 100 1 1000 0.3 10 5 2 10

400 50 50 0.02

carcinogen toxic, carcinogen 300 1 850 2 5600

highly toxic carcinogen

18 9.4 7.9 40 10 0.5 1640 233 234 carcinogen 0.5

1

carcinogen 0.2 carcinogen

50 5 50 25 0.01 3 5 4.7 3 1

176 20 300 0.1 10 7 2 1.4

carcinogen highly toxic highly toxic highly toxic highly toxic highly toxic

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TABLE 11.49 TLV Concentration Limits for Gases and Vapors (Continued) Maximum allowable exposure Substance Hydrogen selenide Hydrogen sulfide 4-Hydroxy-4-methyl-2-pentanone Indene Iodine Iodine pentafluoride Iodomethane Isobutyl acetate Isobutyl alcohol Isopentyl acetate Isopentyl alcohol Isophorone Isopropyl acetate Isopropylamine Isopropylbenzene (cumene) Isopropyl glycidyl ether Ketene Lindane Liquified petroleum gas Malathion Maleic anhydride Malononitrile Mesityl oxide Methacrylic acid Methanethiol Methanol 2-Methoxyaniline (also 4-) 2-Methoxyethanol 2-Methoxyethyl acetate Methyl acetate Methyl acetylene-propadiene (MAPP) Methyl acrylate Methylacrylonitrile Methylamine o-Methylaniline (also p-) m-Methylaniline N-Methylaniline 3-Methyl-1-butanol Methyl tert-butyl ether Methylcyclohexane 1-Methylcyclohexanol cis-2-Methylcyclohexanol trans-2-Methylcyclohexanol cis-3-Methylcyclohexanol trans-3-Methylcyclohexanol cis-4-Methylcyclohexanol trans-4-Methylcyclohexanol Methyl formate 5-Methyl-2-hexanone

ppm

mg · m⫺3

0.05 10 50 10 0.1

0.2 15 238

Toxicity highly toxic highly toxic

1 highly toxic

2 150 50 100 100 5 250 5 50 50 0.5 1000 0.25 0.05 15 20 0.5 200 0.1 5 5 200 1000 10 1 5 2 2 0.5 100 40 400 50 50 50 50 50 50 50 100 50

12 700 150 525 360 28 1040 12 246 240 0.9 0.5 1800 10 1 0.4 60 70 262 carcinogen 16 24 610 1800 35 6.4

highly toxic carcinogen

2.2 361 1600 234 234 234 234 234 234 234 250 234

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TABLE 11.49 TLV Concentration Limits for Gases and Vapors (Continued) Maximum allowable exposure Substance Methyl hydrazine Methyl isocyanate Methyl mercaptan Methyl methacrylate Methyl oxirane 4-Methyl-2-pentanol 4-Methyl-2-pentanone 2-Methyl-2,4-pentanediol 2-Methyl-1-propanol 2-Methyl-2-propanol 2-Methyl-2-propenenitrile o-Methylstyrene (also m-, p-) Morpholine Naphthalene Nickel carbonyl [Ni(CO)4] Nicotine Nitric acid Nitric oxide Nitrobenzene p-Nitrochlorobenzene Nitroethane Nitrogen dioxide Nitrogen trifluoride Nitrogen trioxide Nitroglycerine Nitromethane 1-Nitropropane 2-Nitropropane Nitrosyl chloride o-Nitrotoluene (also m-, p-) Nonane Octachloronaphthalene Octane Oxalic acid 2-Oxetanone Oxygen difluoride Ozone Parathion Pentaborane Pentachloronaphthalene Pentachlorophenol Pentanal Pentane 2-Pentanone 3-Pentanone Pentyl acetate Perchloroethylene Perchloromethyl mercaptan Perchloryl fluoride

ppm 0.01 0.02 0.5 100 20 25 50 25 50 100 1 50 20 10 0.05 2 25 1 100 3 10 10 0.2 100 25 10

mg · m⫺3

0.05 1 410

Toxicity

highly toxic carcinogen

104 205 121 152 303 2.7 70 50 0.35 0.5 5 30 5 1 310

carcinogen

highly toxic

highly toxic 29 2 250 90 36

highly toxic

highly toxic 2 200 300 0.05 0.05 0.1 0.005

50 600 200 200 100 100 0.1 3

1050 0.1 1450 1 carcinogen 0.1 0.2 0.1 0.01 0.5 0.5 1770 700 700 530 670 0.8 14

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TABLE 11.49 TLV Concentration Limits for Gases and Vapors (Continued) Maximum allowable exposure Substance Perfluoroacetone Phenol p-Phenylenediamine Phenylhydrazine Phosgene Phosphine Phosphoric acid Phosphorus pentachloride Phosphorus pentafluoride Phosphorus pentasulfide Phosphorus trichloride Phosphoryl chloride Phthalic anhydride Picric acid— skin Propane Propanoic acid 1-Propanol 2-Propanol Propenal Propenenitrile Propenoic acid Propyl acetate Propyleneimine Propylene oxide Propyl nitrate Propyne 2-Propyn-1-ol Pyridine Quinone Selenium compounds (as Se) Selenium hexafluoride Silane Silicon tetrafluoride Stibine Stoddard solvent Strychnine Styrene Sulfur dioxide Sulfur hexafluoride Sulfuric acid Sulfur monochloride Sulfur pentafluoride Sulfur tetrafluoride Sulfuryl fluoride Tellurium hexafluoride Terphenyls 1,1,2,2-Tetrabromoethane

ppm 0.1 5 0.1 0.1 0.3

mg · m⫺3

Toxicity

19 0.1 0.4 0.4 1 1

carcinogen highly toxic highly toxic

highly toxic 0.5 0.1 1 1000 10 200 400 0.1 2 2 200 2 100 25 1000 1 5 0.1 0.05 5 0.1 100 50 2 1000 1 0.01 0.1 5 0.02 1 1

1 3 6 0.1 1800 30 500 980

low toxicity

carcinogen 835 5 240 110 1650 2.3 15 0.4 0.2 0.4 7

575 0.15 213 6000 1 6 0.4 20 0.2 9 14

carcinogen toxic

highly toxic highly toxic

carcinogen highly toxic low toxicity

highly toxic

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TABLE 11.49 TLV Concentration Limits for Gases and Vapors (Continued) Maximum allowable exposure Substance Tetrabromomethane 1,1,1,2-Tetrachloro-2,2-difluoroethane 1,1,2,2-Tetrachloro-1,2-difluoroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetrachloromethane 1,2,3,4-Tetrachloronaphthalene Tetraethyllead (as Pb) Tetrafluoromethane Tetrahydrofuran Tetramethyllead (as Pb) Tetramethylsuccinonitrile Tetranitromethane Thionyl chloride Thiram Toluene Toluene-2,4-diisocyanate o-Toluidine (also m-, p-) Tribromomethane Tributyl phosphate 1,2,4-Trichlorobenzene 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane Trichloromethane 1,2,3-Trichloropropane 1,1,2-Trichlorotrifluoroethane Tri-o-cresol phosphate (also m-, p-) Triethanolamine Triethylamine Trifluorobromomethane (Freon 13B1) 1,1,2-Trifluorotrichloroethane Triiodomethane Trimethylamine 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene (pseudocumene) 1,3,5-Trimethylbenzene (mesitylene) Trinitrotoluene (TNT) Triphenyl phosphate Turpentine Vinyl acetate Vinyl methyl ether Warfarin o-Xylene (also m-, p-) 2,3-Xylidine (also 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)

ppm 0.1 500 500 1 25 5

mg · m⫺3

4170 4170 6.9 170 31 2 0.100

Toxicity

carcinogen carcinogen carcinogen

low toxicity 200 0.5 1 1 50 0.02 2 0.5 0.2 5 350 10 50 1000 10 10 1000

590 0.150 3 8 5 188 0.14 8.8 5.2 2.2 1910 55 270 5600 49 60

carcinogen carcinogen carcinogen

0.1 0.5 1 1000 1000 0.6 5 25 25 25

6100 7600

100 10

12 123 123 123 1.5 3 560 35

100 0.5

0.1 434 2.5

highly toxic

carcinogen probably anesthetic

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TABLE 11.50 Some Common Reactive and Incompatible Chemicals Chemical Acetic acid

Acetylene Alkali metals

Aluminum Ammonia, anhydrous

Ammonium nitrate Ammonium perchlorate Aniline Benzoyl peroxide

Bromine Calcium carbide Carbon, activated Chlorates

Chlorine

Chlorine dioxide Chlorites Chloroform Chlorosulfonic acid

Chromic(VI) acid

Cobalt Copper

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Keep out of contact with Chromium(VI) oxide, chlorosulfonic acid, ethylene glycol, ethyleneimine, hydroxyl compounds, nitric acid, oleum, perchloric acid, peroxides, permanganates, potasssium tert-butoxide, PCl3 Bromine, chlorine, brass, copper and copper salts, fluorine, mercury and mercury salts, nitric acid, silver and silver salts, alkali hydrides, potassium metal Moisture, acetylene, metal halides, ammonium salts, oxygen and oxidizing agents, halogens, carbon tetrachloride, carbon, carbon dioxide, carbon disulfide, chloroform, chlorinated hydrocarbons, ethylene oxide, boric acid, sulfur, tellurium Chlorinated hydrocarbons, halogens, steam Mercury, halogens, hypochlorites, chlorites, chlorine(I) oxide, hydrofluoric acid (anhydrous), hydrogen peroxide, chromium(VI) oxide, nitrogen dioxide, chromyl(VI) chloride, sulfinyl chloride, magnesium perchlorate, peroxodisulfates, phosphorus pentoxide, acetaldehyde, ethylene oxide, acrolein, gold(III) chloride Acids, metal powders, flammable liquids, chlorates, nitrites, sulfur, finely divided organic or combustible materials, perchlorates, urea Hot copper tubing, sugar, finely divided organic or combustible materials, potassium periodate and permanganate, powdered metals, carbon, sulfur Nitric acid, peroxides, oxidizing materials, acetic anhydride, chlorosulfonic acid, oleum, ozone Direct sunlight, sparks and open flames, shock and friction, acids, alcohols, amines, ethers, reducing agents, polymerization catalysts, metallic naphthenates Ammonia, carbides, dimethylformamide, fluorine, ozone, olefins, reducing materials including many metals, phosphine, silver azide Moisture, selenium, silver nitrate, sodium peroxide, tin(II) chloride, potassium hydroxide plus chlorine, HCl gas, magnesium Calcium hypochlorite, all oxidizing agents, unsaturated oils Ammonium salts, acids, metal powders, sulfur, finely divided organic or combustible materials, cyanides, metal sulfides, manganese dioxide, sulfur dioxide, organic acids Ammonia, acetylene, alcohols, alkanes, benzene, butadiene, carbon disulfide, dibutyl phthalate, ethers, fluorine, glycerol, hydrocarbons, hydrogen, sodium carbide, finely divided metals, metal acetylides and carbides, nitrogen compounds, nonmetals, nonmetal hydrides, phosphorus compounds, polychlorobiphenyl, silicones, steel, sulfides, synthetic rubber, turpentine Ammonia, carbon monoxide, hydrogen, hydrogen sulfide, methane, mercury, nonmetals, phosphine, phosphorus pentachloride Ammonia, organic matter, metals Aluminum, magnesium, potassium, sodium, aluminum chloride, ethylene, powerful oxidants Saturated and unsaturated acids, acid anhydrides, nitriles, acrolein, alcohols, ammonia, esters, HCl, HF, ketones, hydrogen peroxide, metal powders, nitric acid, organic materials, water Acetic acid, acetic anhydride, acetone, alcohols, alkali metals, ammonia, dimethylformamide, camphor, glycerol, hydrogen sulfide, phosphorus, pyridine, selenium, sulfur, turpentine, flammable liquids in general Acetylene, hydrazinium nitrate, oxidants Acetylene and alkynes, ammonium nitrate, azides, bromates, chlorates, iodates, chlorine, ethylene oxide, fluorine, peroxides, hydrogen sulfide, hydrazinium nitrate

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TABLE 11.50 Some Common Reactive and Incompatible Chemicals (Continued) Chemical Copper(II) sulfate Cumene hydroperoxide Cyanides Cyclohexanol Cyclohexanone Decaborane-14 Diazomethane 1,1-Dichloroethylene Dimethylformamide 1,1-Dimethylhydrazine Dimethylsulfoxide

Dinitrobenzenes Dinitrotoluenes 1,4-Dioxane Esters Ethylamine Ethers Ethylene Ethylene oxide

Ethyl ether Ethyl sulfate Flammable liquids Fluorine Formamide Freon 113 Glycerol Hydrazine

Hydrides Hydrocarbons Hydrogen Hydrogen bromide Hydrogen chloride

Hydrogen fluoride

Hydrogen iodide Hydrogen peroxide Hydrogen selenide Hydrogen sulfide

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Keep out of contact with Hydroxylamine, magnesium Acids (inorganic or organic) Acids, water or steam, fluorine, magnesium, nitric acid and nitrates, nitrites Oxidants Hydrogen peroxide, nitric acid Dimethyl sulfoxide, ethers, halocarbons Alkali metals, calcium sulfate Air, chlorotrifluoroethylene, ozone, perchloryl fluoride Halocarbons, inorganic and organic nitrates, bromine, chromium(VI) oxide, aluminum trimethyl, phosphorus trioxide Air, hydrogen peroxide, nitric acid, nitrous oxide Acyl and aryl halides, boron compounds, bromomethane, nitrogen dioxide, magnesium perchlorate, periodic acid, silver difluoride, sodium hydride, sulfur trioxide Nitric acid Nitric acid Silver perchlorate Nitrates Cellulose, oxidizers Oxidizing materials, boron triiodide Aluminum trichloride, carbon tetrachloride, chlorine, nitrogen oxides, tetrafluoroethylene Acids and bases, alcohols, air, 1,3-nitroaniline, aluminum chloride, aluminum oxide, ammonia, copper, iron chlorides and oxides, magnesium perchlorate, mercaptans, potassium, tin chlorides, alkane thiols Liquid air, chlorine, chromium(VI) oxide, lithium aluminum hydride, ozone, perchloric acid, peroxides Oxidizing materials, water Ammonium nitrate, chromic acid, the halogens, hydrogen peroxide, nitric acid Isolate from everything; only lead and nickel resist prolonged attack Iodine, pyridine, sulfur trioxide Aluminum, barium, lithium, samarium, NaK alloy, titanium Acetic anhydride, hypochlorites, chromium(VI) oxide, perchlorates, alkali peroxides, sodium hydride Alkali metals, ammonia, chlorine, chromates and dichromates, copper salts, fluorine, hydrogen peroxide, metallic oxides, nickel, nitric acid, liquid oxygen, zinc diethyl Powerful oxidizing agents, moisture Halogens, chromium(VI) oxide, peroxides Halogens, lithium, oxidants, lead trifluoride Fluorine, iron(III) oxide, ammonia, ozone Acetic anhydride, aluminum, 2-aminoethanol, ammonia, chlorosulfonic acid, ethylenediamine, fluorine, metal acetylides and carbides, oleum, perchloric acid, potassium permanganate, sodium, sulfuric acid Acetic anhydride, 2-aminoethanol, ammonia, arsenic trioxide, chlorosulfonic acid, ethylenediamine, ethyleneimine, fluorine, HgO, oleum, phosphorus trioxide, propylene oxide, sodium, sulfuric acid, vinyl acetate Fluorine, nitric acid, ozone, metals Copper, chromium, iron, most metals or their salts, alcohols, acetone, organic materials, flammable liquids, combustible materials Hydrogen peroxide, nitric acid Fuming nitric acid, oxidizing gases, peroxides

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TABLE 11.50 Some Common Reactive and Incompatible Chemicals (Continued) Chemical Hydroquinone Hydroxylamine

Hypochlorites, salts of Indium Iodine

Iodine monochloride Iodoform Iodomethane Iron disulfide Isothiourea Ketones Lactonitrile Lead Lead(II) azide Lead chromate Lead dioxide

Lead(II) oxide Lead(II,IV) oxide Lithium hydride Magnesium

Maleic anhydride Manganese dioxide Mercaptans Mercury Mercury(II) cyanide Mercury(I) nitrate Mercury(II) nitrate Mercury(II) oxide Mesityl oxide Methanol Methylamine N-Methylformamide Methyl isobutyl ketone

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Keep out of contact with Sodium hydroxide Barium oxide and peroxide, carbonyls, chlorine, copper(II) sulfate, dichromates, lead dioxide, phosphorus trichloride and pentachloride, permanganates, pyridine, sodium, zinc Urea, amines, anthracene, carbon, carbon tetrachloride, ethanol, glycerol, mercaptans, organic sulfides, sulfur, thiols Acetonitrile, nitrogen dioxide, mercury(II) bromide, sulfur Acetaldehyde, acetylene, aluminum, ammonia (aqueous or anhydrous), antimony, bromine pentafluoride, carbides, cesium oxide, chlorine, ethanol, fluorine, formamide, lithium, magnesium, phosphorus, pyridine, silver azide, sulfur trioxide Aluminum foil, organic matter, metal sulfides, phosphorus, potassium, rubber, sodium Acetone, lithium, mercury(II) oxide, mercury(I) chloride, silver nitrate Silver chlorite, sodium Water, powdered pyrites Acrylaldehyde, hydrogen peroxide, nitric acid Aldehydes, nitric acid, perchloric acid Oxidizing materials Ammonium nitrate, chlorine trifluoride, hydrogen peroxide, sodium azide and carbide, zirconium, oxidants Calcium stearate, copper, zinc, brass, carbon disulfide Iron hexacyanoferrate(4– ) Aluminum carbide, hydrogen peroxide, hydrogen sulfide, hydroxylamine, nitroalkanes, nitrogen compounds, nonmetal halides, peroxoformic acid, phosphorus, phosphorus trichloride, potassium, sulfur, sulfur dioxide, sulfides, tungsten, zirconium Chlorinated rubber, chlorine, ethylene, fluorine, glycerol, metal acetylides, perchloric acid Same as for lead dioxide Nitrous oxide, oxygen Air, beryllium fluoride, ethylene oxide, halogens, halocarbons, HI, metal cyanides, metal oxides, metal oxosalts, methanol, oxidants, peroxides, sulfur, tellurium Alkali metals, amines, KOH, NaOH, pyridine Aluminum, hydrogen sulfide, oxidants, potassium azide, hydrogen peroxide, peroxosulfuric acid, sodium peroxide Powerful oxidizers Acetylenic compounds, chlorine, fulminic acid, ammonia, ethylene oxide, metals, methyl azide, oxidants, tetracarbonylnickel Fluorine, hydrogen cyanide, magnesium, sodium nitrite Phosphorus Acetylene, aromatics, ethanol, hypophosphoric acid, phosphine, unsaturated organic compounds Chlorine, hydrazine hydrate, hydrogen peroxide, hypophosphorous acid, magnesium, phosphorus, sulfur, butadiene, hydrocarbons, methanethiol 2-Aminoethanol, chlorosulfonic acid, nitric acid, ethylenediamine, sulfuric acid Beryllium dihydride, chloroform, oxidants, potassium tert-butoxide Nitromethane Benzenesulfonyl chloride Potassium tert-butoxide

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TABLE 11.50 Some Common Reactive and Incompatible Chemicals (Continued) Chemical Methyl methacrylate 4-Methylnitrobenzene 2-Methylpyridine Methylsodium Molybdenum trioxide Naphthalene 2-Naphthol Neodymium Nickel Nickel carbonyl Niobium Nitrates Nitric acid, fuming

Nitric oxide

Nitrites Nitrobenzene Nitroethane Nitrogen trichloride Nitrogen dioxide Nitrogen triiodide ␣-Nitroguanidine Nitromethane 1-Nitropropane Nitrosyl fluoride Nitrosyl perchlorate Nitrourea Nitrous acid Nitryl chloride Oxalic acid Oxygen

Ozone Palladium Paraformaldehyde Paraldehyde Pentaborane-9 Pentacarbonyliron

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Keep out of contact with Air, benzoyl peroxide Sulfuric acid, tetranitromethane Hydrogen peroxide, iron(II) sulfate, sulfuric acid 4-Chloronitrobenzene Chlorine trifluoride, interhalogens, metals Chromium trioxide, dinitrogen pentaoxide Antipyrine, camphor, phenol, iron(III) salts, menthol, oxidizing materials, permanganates, urethane Phosphorus Aluminum, aluminum(III) chloride, ethylene, 1,4-dioxan, hydrogen, methanol, nonmetals, oxidants, sulfur compounds Air, bromine, oxidizing materials Bromine trifluoride, chlorine, fluorine Aluminum, BP, cyanides, esters, phosphorus, tin(II) chloride, sodium hypophosphite, thiocyanates Organic matter, nonmetals, most metals, ammonia, chlorosulfonic acid, chromium trioxide, cyanides, dichromates, hydrazines, hydrides, HCN, HI, hydrogen sulfide, sulfur dioxide, sulfur halides, sulfuric acid, flammable liquids and gases Aluminum, BaO, boron, carbon disulfide, chromium, many chlorinated hydrocarbons, fluorine, hydrocarbons, ozone, phosphine, phosphorus, hydrazine, acetic anhydride, ammonia, chloroform, Fe, K, Mg, Mn, Na, sulfur Organic nitrites in contact with ammonium salts, cyanides Nitric acid, nitrous oxide, silver perchlorate Hydroxides, hydrocarbons, metal oxides Ammonia, As, hydrogen sulfide, nitrogen dioxide, organic matter, ozone, phosphine, phosphorus, KCN, KOH, Se, dibutyl ether Cyclohexane, fluorine, formaldehyde, alcohols, nitrobenzene, petroleum, toluene Acids, bromine, chlorine, hydrogen sulfide, ozone Complex salts of mercury and silver Acids, alkylmetal halides, hydroxides, hydrocarbons, organic amines, formaldehyde, nitric acid, perchlorates See under Nitromethane; chlorosulfonic acid, oleum Haloalkenes, metals, nonmetals Acetones, amines, diethyl ether, metal salts, organic materials Mercury(II) and silver salts Phosphine, phosphorus trichloride, silver nitrate, semicarbazone Ammonia, sulfur trioxide, tin(IV) bromide and iodide Furfuryl alcohol, silver, mercury, sodium chlorate, sodium chlorite, sodium hypochlorite Acetaldehyde, acetone, alcohols, alkali metals, alkaline earth metals, Al-Ti alloys, ether, carbon disulfide, halocarbons, hydrocarbons, metal hydrides, 1,3,5-trioxane Alkenes, aromatic compounds, bromine, diethyl ether, ethylene, HBr, HI, nitric oxide, nitrogen dioxide, rubber, stibine Arsenic, carbon, ozonides, sulfur, sodium tetrahydridoborate Liquid oxygen Alkalies, HCN, iodides, nitric acid, oxidizers Dimethylsulfoxide Acetic acid, nitric oxide, transition metal halides, water, zinc

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TABLE 11.50 Some Common Reactive and Incompatible Chemicals (Continued) Chemical 2-Pentanone 3-Pentanone Perchlorates Perchloric acid

Permanganates Peroxides Peroxoacetic acid Peroxobenzoic acid Peroxoformic acid Peroxosulfuric acid Phenol Phenylhydrazine Phosgene Phosphine Phosphorus pentachloride Phosphorus pentafluoride Phosphorus pentasulfide Phosphorus pentoxide Phosphorus, red Phosphorus tribromide Phosphorus trichloride

Phosphorus, white Phosphoryl chloride Phthalic acid Piperazine Platinum Potassium Potassium tert-butoxide Potassium hydride Potassium perchlorate Potassium permanganate Potassium sodium alloy 2-Propyn-1-ol Pyridine Pyrrolidine

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Keep out of contact with Bromine trifluoride Hydrogen peroxide, nitric acid Carbonaceous materials, finely divided metals particularly magnesium and aluminum, sulfur, benzene, olefins, ethanol, sulfur, sulfuric acid Acetic acid, acetic anhydride, alcohols, antimony compounds, azo pigments, bismuth and its alloys, methanol, carbonaceous materials, carbon tetrachloride, cellulose, dehydrating agents, diethyl ether, glycols and glycolethers, HCl, HI, hypophosphites, ketones, nitric acid, pyridine, steel, sulfoxides, sulfuric acid All reducing agents, organic materials Reducing agents, organic materials, thiocyanates Acetic anhydride, olefins, organic matter Olefins, reducing materials Metals and nonmetals, organic materials Acetone, alcohols, aromatic compounds, catalysts Butadiene, peroxodisulfuric acid, peroxosulfuric acid, aluminum chloride plus nitrobenzene Lead dioxide, oxidizers Aluminum, alkali metals, 2-propanol Air, boron trichloride, bromine, chlorine, nitric acid, nitrogen oxides, nitrous acid, oxygen, silver nitrate Aluminum, chlorine, chlorine dioxide, chlorine trioxide, fluorine, magnesium oxide, nitrobenzene, diphosphorus trioxide, potassium, sodium, urea, water Water or steam Air, alcohols, water Formic acid, HF, inorganic bases, metals, oxidants, water Organic materials Potassium, ruthenium tetroxide, sodium, water Acetic acid, aluminum, chromyl dichloride, dimethylsulfoxide, hydroxylamine, lead dioxide, nitric acid, nitrous acid, organic matter, potassium, sodium water Air, oxidants of all types, halogens, metals Carbon disulfide, N,N-dimethylformamide, 2,5-dimethylpyrrole, 2,6-dimethylpyridine 1-oxide, dimethylsulfoxide, water, zinc Nitric acid, sodium nitrite Oxidizers Acetone, arsenic, hydrazine, lithium, proxosulfuric acid, phosphorus, selenium, tellurium See under Alkali metals Organic compounds, sulfuric acid Air, chlorine, acetic acid, acrolein, acrylonitrile, maleic anhydride, nitroparaffins, N-nitrosomethylurea, tetrahydrofuran, water Aluminum plus magnesium, carbon, nickel plus titanium, reducing agents, sulfur, sulfuric acid Organic or readily oxidizable materials Air, carbon dioxide, carbon disulfide, halocarbons, metal oxides Alkali metals, mercury(II) sulfate, oxidizing materials, phosphorus pentoxide, sulfuric acid Chlorosulfonic acid, chromium trioxide, formamide, maleic anhydride, nitric acid, oleum, perchromates, silver perchlorate, sulfuric acid Oxidizing materials

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TABLE 11.50 Some Common Reactive and Incompatible Chemicals (Continued) Chemical Quinoline Salicylic acid Silicon Silver Sodium Sodium peroxide

Sulfides Sulfur Sulfur dioxide Sulfuric acid Sulfuryl dichloride Tellurium Tetrahydrofuran Tetranitroaniline Tetranitromethane Thiocyanates Thionyl chloride Thiophene Thymol Tin(II) chloride Tin(IV) chloride Titanium

Toluene Toluidines 2,4,6-Trinitrotoluene 1,3,5-Trioxane Urea Vinylidene chloride

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Keep out of contact with Dinitrogen tetroxide, linseed oil, maleic anhydride, thionyl chloride Iodine, iron salts, lead acetate Alkali carbonates, calcium, chlorine, cobalt(II) fluoride, manganese trifluoride, oxidants, silver fluoride, sodium-potassium alloy Acetylene, ammonium compounds, ethyleneimine, hydrogen peroxide, oxalic acid, sulfuric acid, tartaric acid See under Alkali metals Glacial acetic acid, acetic anhydride, aniline, benzene, benzaldehyde, carbon disulfide, diethyl ether, ethanol or methanol, ethylene glycol, ethyl acetate, furfural, glycerol, metals, methyl acetate, organic matter Acids, powerful oxidizers, moisture Oxidizing materials, halogens Halogens, metal oxides, polymeric tubing, potassium chlorate, sodium hydride Chlorates, metals, HCl, organic materials, perchlorates, permanganates, water Alkalis, diethyl ether, dimethylsulfoxide, dinitrogen tetroxide, lead dioxide, phosphorus Halogens, metals Tetrahydridoaluminates, KOH, NaOH Reducing materials Aluminum, cotton, aromatic nitro compounds, hydrocarbons, cotton, toluene Chlorates, nitric acid, peroxides Ammonia, dimethylsulfoxide, linseed oil, quinoline, sodium Nitric acid Acetanilide, antipyrine, camphor, chlorohydrate, menthol, quinine sulfate, urethene Boron trifluoride, ethylene oxide, hydrazine hydrate, nitrates, Na, K, hydrogen peroxide Alkyl nitrates, ethylene oxide, K, Na turpentine Aluminum, boron trifluoride, carbon dioxide, CuO, halocarbons, halogens, PbO, nitric acid, potassium chlorate, potassium nitrate, potassium permanganate, steam at high temperatures, water Sulfuric plus nitric acids, nitrogen dioxide, silver perchlorate, uranium hexafluoride Nitric acid Sodium dichromate, sulfuric acid Oxidizing materials, acids Sodium nitrite, phosphorus pentachloride Chlorosulfonic acid, nitric acid, oleum

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TABLE 11.51 Chemicals Recommended for Refrigerated Storage A. Due to chemical decomposition or polymerization Acetaldehyde Acrolein Adenosinetriphosphoric acid Bromacetaldehyde, diethyl acetal Bromosuccinimide 3-Buten-2-one tert-Butyl hydroperoxide 2-Chlorocyclohexanone Cupferron 1,3-Cyclohexadiene 1,3-Dihydroxy-2-propanone Divinylbenzene Ethyl methacrylate, monomer Glutathione Glycidol Histamine, base Hydrocinnamaldehyde

Isoprene Lecithin Mercaptoacetic acid Methyl acrylate 2-Methyl-1-butene Methylenedi-1,4-phenylene diisocyanate 4-Methyl-1-pentene ␣-Methylstyrene 1-Naphthyl isocyanate 1-Pentene Isopentyl acetate Pyruvic acid Styrene, stabilized Tetramethylsilane Thioacetamide Veratraldehyde Vitamin E (and the acetate)

B. Due to flammability and high volatility Acetaldehyde Bromoethane tert-Butylamine Carbon disulfide 1-Chloropropane 3-Chloropropane Cyclopentane Diethyl ether 2,2-Dimethylbutane Dimethyl sulfide Furan

Iodomethane Isoprene Isopropylamine Methylal 2-Methylbutane 2-Methyl-2-butene Methyl formate Pentane Propylamine Propylene oxide Trichlorosilane

TABLE 11.52 Chemicals Which Polymerize or Decompose on Extended Refrigeration Formaldehyde Hydrogen peroxide Sodium chlorite [sodium chlorate (IV)] Sodium chromate(VI) Sodium dithionite Sodium ethoxide

Sodium methoxide Sodium nitrate Sodium peroxide Strontium nitrate Urea

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SIEVES AND SCREENS

TABLE 11.53 U.S. Standard Sieve Series Sieve opening

Sieve opening

Sieve no.

mm

inch

Sieve no.

mm

inch

3.5 4 5 6 7 8

125 106 90 75 63 53 45 37.5 31.5 26.5 22.4 19.0 16.0 13.2 11.2 9.5 8.0 6.7 5.60 4.75 4.00 3.35 2.80 2.36

5.00 4.24 3.50 3.00 2.50 2.12 1.75 1.50 1.25 1.06 0.875 0.75 0.625 0.530 0.438 0.375 0.312 0.265 0.223 0.187 0.157 0.132 0.111 0.0937

10 12 14 16 18 20 25 30 35 40 45 50 60 70 80 100 120 140 170 200 230 270 325 400

2.00 1.70 1.40 1.18 1.00 0.850 0.710 0.600 0.500 0.425 0.355 0.300 0.250 0.212 0.180 0.150 0.125 0.106 0.090 0.075 0.063 0.053 0.045 0.038

0.0787 0.0661 0.0555 0.0469 0.0394 0.0331 0.0278 0.0234 0.0197 0.0165 0.0139 0.0117 0.0098 0.0083 0.0070 0.0059 0.0049 0.0041 0.0035 0.0029 0.0025 0.0021 0.0017 0.0015

Specifications are from ASTM E.11-81/ISO 565. The sieve numbers are the approximate number of openings per linear inch.

11.9 11.9.1

THERMOMETRY Temperature and Its Measurement

The new international temperature scale, known as ITS-90, was adopted in September 1989. However, neither the definition of thermodynamic temperature nor the definition of the kelvin or the Celsius temperature scales has changed; it is the way in which we are to realize these definitions that has changed. The changes concern the recommended thermometers to be used in different regions of the temperature scale and the list of secondary standard fixed points. The changes in temperature determined using ITS-90 from the previous IPTS-68 are always less than 0.4 K, and almost always less than 0.2 K, over the range 0–1300 K. The ultimate definition of thermodynamic temperature is in terms of pV (pressure ⫻ volume) in a gas thermometer extrapolated to low pressure. The kelvin (K), the unit of thermodynamic temperature, is defined by specifying the temperature of one fixed point on the scale— the triple point

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of water which is defined to be 273.16 K. The Celsius temperature scale (⬚C) is defined by the equation

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⬚C ⫽ K ⫺ 273.15 where the freezing point of water at 1 atm is 273.15 K. The fixed points in the ITS-90 are given in Table 11.39. Platinum resistance thermometers are recommended for use between 14 K and 1235 K (the freezing point of silver), calibrated against the fixed points. Below 14 K either the vapor pressure of helium or a constant-volume gas thermometer is to be used. Above 1235 K radiometry is to be used in conjunction with the Planck radiation law, L␭ ⫽ c1␭⫺5 (ec2/␭T ⫺ 1)⫺1 where L␭ is the spectral radiance at wavelength ␭. The first radiation constant, c1 , is 3.741 83 ⫻ 10⫺16 W · m2 and the second radiation constant, c2 , has a value of 0.014 388 m · K.

TABLE 11.54 Fixed Points in the ITS-90 T, K

t, ⬚C

Triple point of hydrogen Boiling point of hydrogen at 33 321.3 Pa Boiling point of hydrogen at 101 292 Pa Triple point of neon Triple point of oxygen Triple point of argon Triple point of mercury Triple point of water Melting point of gallium Freezing point of indium Freezing point of tin Freezing point of zinc Freezing point of aluminum Freezing point of silver Freezing point of gold Freezing point of copper

13.8033 17.035 20.27 24.5561 54.3584 83.8058 234.3156 273.16 302.9146 429.7458 505.078 692.677 933.473 1234.93 1337.33 1357.77

⫺259.3467 ⫺256.115 ⫺252.88 ⫺248.5939 ⫺218.7916 ⫺189.3442 ⫺38.8344 0.01 29.7646 156.5985 231.928 419.527 660.323 961.78 1064.18 1084.62

Secondary reference points to extend the scale (IPTS-68): Freezing point of platinum Freezing point of rhodium Freezing point of iridium Melting point of tungsten

2042 2236 2720 3660

Fixed points

11.10

1769 1963 2447 3387

THERMOCOUPLES

The thermocouple reference data in Tables 11.55 to 11.63 give the thermoelectric voltage in millivolts with the reference junction at 0⬚C. Note that the temperature for a given entry is obtained by adding the corresponding temperature in the top row to that in the left-hand column, regardless of whether the latter is positive or negative.

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The noble metal thermocouples, Types B, R, and S, are all platinum or platinum-rhodium thermocouples and hence share many of the same characteristics. Metallic vapor diffusion at high temperatures can readily change the platinum wire calibration, hence platinum wires should only be used inside a nonmetallic sheath such as high-purity alumina. Type B thermocouples (Table 11.56) offer distinct advantages of improved stability, increased mechanical strength, and higher possible operating temperatures. They have the unique advantage that the reference junction potential is almost immaterial, as long as it is between 0⬚C and 40⬚C. Type B is virtually useless below 50⬚C because it exhibits a double-value ambiguity from 0⬚C to 42⬚C. Type E thermoelements (Table 11.57) are very useful down to about liquid hydrogen temperatures and may even be used down to liquid helium temperatures. They are the most useful of the commercially standardized thermocouple combinations for subzero temperature measurements because of their high Seebeck coefficient (58 ␮V/⬚C), low thermal conductivity, and corrosion resistance. They also have the largest Seebeck coefficient (voltage response per degree Celsius) above 0⬚C of any of the standardized thermocouples which makes them useful for detecting small temperature changes. They are recommended for use in the temperature range from ⫺250 to 871⬚C in oxidizing or inert atmospheres. They should not be used in sulfurous, reducing, or alternately reducing and oxidizing atmospheres unless suitably protected with tubes. They should not be used in vacuum at high temperatures for extended periods of time. Type J thermocouples (Table 11.58) are one of the most common types of industrial thermocouples because of the relatively high Seebeck coefficient and low cost. They are recommended for use in the temperature range from 0 to 760⬚C (but never above 760⬚C due to an abrupt magnetic transformation that can cause decalibration even when returned to lower temperatures). Use is permitted in vacuum and in oxidizing, reducing, or inert atmospheres, with the exception of sulfurous atmospheres above 500⬚C. For extended use above 500⬚C, heavy-gauge wires are recommended. They are not recommended for subzero temperatures. These thermocouples are subject to poor conformance characteristics because of impurities in the iron. The Type K thermocouple (Table 11.59) is more resistant to oxidation at elevated temperatures than the Type E, J, or T thermocouple, and consequently finds wide application at temperatures above 500⬚C. It is recommended for continuous use at temperatures within the range ⫺250 to 1260⬚C in inert or oxidizing atmospheres. It should not be used in sulfurous or reducing atmospheres, or in vacuum at high temperatures for extended times. The Type N thermocouple (Table 11.60) is similar to Type K but it has been designed to minimize some of the instabilities in the conventional Chromel-Alumel combination. Changes in the alloy content have improved the order/disorder transformations occurring at 500⬚C and a higher silicon content of the positive element improves the oxidation resistance at elevated temperatures. The Type R thermocouple (Table 11.61) was developed primarily to match a previous platinum– 10% rhodium British wire which was later found to have 0.34% iron impurity in the rhodium. Comments on Type S also apply to Type R. The Type S thermocouple (Table 11.62) is so stable that it remains the standard for determining temperatures between the antimony point (630.74⬚C) and the gold point (1064.43⬚C). The other fixed point used is that of silver. The Type S thermocouple can be used from ⫺50⬚C continuously up to about 1400⬚C, and intermittently at temperatures up to the freezing point of platinum (1769⬚C). The thermocouple is most reliable when used in a clean oxidizing atmosphere, but may also be used in inert gaseous atmospheres or in a vacuum for short periods of time. It should not be used in reducing atmospheres, nor in those containing metallic vapor (such as lead or zinc), nonmetallic vapors (such as arsenic, phosphorus, or sulfur), or easily reduced oxides, unless suitably protected with nonmetallic protecting tubes. The Type T thermocouple (Table 11.63) is popular for the temperature region below 0⬚C (but see under Type E). It can be used in vacuum, or in oxidizing, reducing, or inert atmospheres.

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TABLE 11.55 Thermoelectric Values in Millivolts at Fixed Points for Various Thermocouples

Fixed point

⬚C

Helium NPB Hydrogen TP Hydrogen NBP Neon TP Neon NBP Oxygen TP Nitrogen TP Nitrogen NBP Oxygen NBP Carbon dioxide SP Mercury TP Ice point Diphenyl ether TP Water BP

⫺268.934 ⫺259.347* ⫺252.88* ⫺248.594* ⫺246.048 ⫺218.792* ⫺210.001 ⫺195.802 ⫺182.962 ⫺78.474 ⫺38.834* 0.000 26.87 100.00

Type B

Type E

⫺0.000 ⫺0.0024 0.0332

⫺9.8331 ⫺9.7927 ⫺9.7447 ⫺9.7046 ⫺9.6776 ⫺9.2499 ⫺9.0629 ⫺8.7168 ⫺8.3608 ⫺4.2275 ⫺2.1930 0.000 1.6091 6.3171

Type J

⫺8.0957 ⫺7.7963 ⫺7.4807 ⫺3.7187 ⫺1.4849 0.000 1.3739 5.2677

Type K

Type N

⫺6.4569 ⫺6.4393 ⫺6.4167 ⫺6.3966 ⫺6.3827 ⫺6.1446 ⫺6.0346 ⫺5.8257 ⫺5.6051 ⫺2.8696

⫺4.345 ⫺4.334 ⫺4.321 ⫺4.271 ⫺4.300 ⫺4.153 ⫺4.083 ⫺3.947 ⫺3.802 ⫺1.939 ⫺0.985 0.000 0.698 2.774

0.000 1.076 4.0953

Type R

⫺0.1830 0.000 0.1517 0.6472

Type S

Type T

⫺0.1895 0.000 0.1537 0.6453

⫺6.2563 ⫺6.2292 ⫺6.1977 ⫺6.1714 ⫺6.1536 ⫺5.8730 ⫺5.7533 ⫺5.5356 ⫺5.3147 ⫺2.7407 ⫺1.4349 0.000 1.0679 4.2773

(McGHP)

Abbreviations Used in the Table FP, freezing point BP, boiling point NBP, normal boiling point TP, triple point

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TABLE 11.55 Thermoelectric Values in Millivolts at Fixed Points for Various Thermocouples (Continued) Abbreviations Used in the Table FP, freezing point BP, boiling point NBP, normal boiling point TP, triple point ⬚C

Type B

Type E

Type J

Type K

Type N

Type R

Type S

Type T

Benzoic acid TP Indium FP Tin FP Bismuth FP Cadmium FP Lead FP Mercury BP Zinc FP Cu-Al eutectic FP Antimony FP Aluminum FP Silver FP Gold FP Copper FP Nickel FP Cobalt FP Palladium FP Platinum FP

122.37 156.598* 231.928* 271.442 321.108 327.502 356.66 419.527* 548.23 630.74 660.37 961.93* 1064.43* 1084.5 1455 1494 1554 1772

0.0561 0.1019 0.2474 0.3477 0.4971 0.5182 0.6197 0.8678 1.4951 1.9784 2.1668 4.4908 5.4336 5.6263 9.5766 10.025 10.721 13.262

7.8468 10.260 15.809 18.821 22.684 23.186 25.489 30.513 40.901 47.561 49.941 73.495

6.4886 8.3743 12.552 14.743 17.493 17.846 19.456 22.926 30.109 34.911 36.693 55.669 61.716 62.880

5.0160 6.0404 9.4201 11.029 13.085 13.351 14.571 17.223 22.696 26.207 27.461 39.779 43.755 44.520

3.446 4.508 6.980 8.336 10.092 10.322

0.8186 1.0956 1.7561 2.1250 2.6072 2.6706 2.9630 3.6113 5.0009 5.9331 6.2759 10.003 11.364 11.635 16.811 17.360 18.212 21.103

0.8129 1.0818 1.7146 2.0640 2.5167 2.5759 2.8483 3.4479 4.7140 5.5521 5.8591 9.1482 10.334 10.570 15.034 15.504 16.224 18.694

5.3414 7.0364 11.013 13.219 16.095 16.473 18.218

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* Defining fixed points of the International Temperature Scale of 1990 (ITS-90). Except for the triple points, the assigned values of temperature are for equilibrium states at a pressure of one standard atmosphere (101 325 Pa).

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TABLE 11.56 Type B Thermocouples: Platinum– 30% Rhodium Alloy vs. Platinum– 6% Rhodium Alloy

(McGHP)

Thermoelectric voltage in millivolts; reference junction at 0⬚C. 0

10

20

30

40

50

60

70

80

90

0 100 200 300 400 500 600 700 800 900 1000 1100 1200 1300 1400 1500 1600 1700 1800

0.00 0.0332 0.1782 0.4305 0.7864 1.2415 1.7912 2.4305 3.1540 3.9565 4.8326 5.7769 6.7833 7.8446 8.9519 10.0940 11.2574 12.4263 13.5845

⫺0.0019 0.0427 0.1987 0.4615 0.8275 1.2923 1.8512 2.4991 3.2308 4.0409 4.9241 5.8749 6.8871 7.9534 9.0648 10.2097 11.3743 12.5429 13.6991

⫺0.0026 0.0534 0.2202 0.4935 0.8696 1.3440 1.9120 2.5686 3.3084 4.1260 5.0162 5.9734 6.9914 8.0627 9.1780 10.3255 11.4913 12.6594 13.8135

⫺0.0021 0.0652 0.2428 0.5266 0.9127 1.3967 1.9738 2.6390 3.3867 4.2119 5.1090 6.0726 7.0963 8.1724 9.2915 10.4415 11.6082 12.7757

⫺0.0005 0.0780 0.2665 0.5607 0.9567 1.4503 2.0365 2.7101 3.4658 4.2984 5.2025 6.1724 7.2017 8.2826 9.4053 10.5577 11.7252 12.8918

0.0023 0.0920 0.2912 0.5958 1.0018 1.5048 2.1000 2.7821 3.5457 4.3857 5.2966 6.2728 7.3076 8.3932 9.5194 10.6740 11.8422 13.0078

0.0062 0.1071 0.3170 0.6319 1.0478 1.5603 2.1644 2.8548 3.6264 4.4737 5.3914 6.3737 7.4140 8.5041 9.6338 10.7905 11.9591 13.1236

0.0112 0.1232 0.3438 0.6690 1.0948 1.6166 2.2296 2.9284 3.7078 4.5624 5.4868 6.4753 7.5210 8.6155 9.7485 10.9071 12.0761 13.2391

0.0174 0.1405 0.3717 0.7071 1.1427 1.6739 2.2957 3.0028 3.7899 4.6518 5.5829 6.5774 7.6284 8.7273 9.8634 11.0237 12.1929 13.3545

0.0248 0.1588 0.4006 0.7462 1.1916 1.7321 2.3627 3.0780 3.8729 4.7419 5.6796 6.6801 7.7363 8.8394 9.9786 11.1405 12.3100 13.4696

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TABLE 11.57 Type E Thermocouples: Nickel-Chromium Alloy vs. Copper-Nickel Alloy Thermoelectric voltage in millivolts; reference junction at 0⬚C. 0

10

20

30

40

50

60

70

80

90

⫺200 ⫺100 ⫺0 0 100 200 300 400 500 600 700 800 900 1000

⫺8.824 ⫺5.237 0.000 0.000 6.317 13.419 21.033 28.943 36.999 45.085 53.110 61.022 68.783 76.358

⫺9.063 ⫺5.680 ⫺0.581 0.591 6.996 14.161 21.814 29.744 37.808 45.891 53.907 61.806 69.549

⫺9.274 ⫺6.107 ⫺1.151 1.192 7.683 14.909 22.597 30.546 38.617 46.697 54.703 62.588 70.313

⫺9.455 ⫺6.516 ⫺1.709 1.801 8.377 15.661 23.383 31.350 39.426 47.502 55.498 63.368 71.075

⫺9.604 ⫺6.907 ⫺2.254 2.419 9.078 16.417 24.171 32.155 40.236 48.306 56.291 64.147 71.835

⫺9.719 ⫺7.279 ⫺2.787 3.047 9.787 17.178 24.961 32.960 41.045 49.109 57.083 64.924 72.593

⫺9.797 ⫺7.631 ⫺3.306 3.683 10.501 17.942 25.754 33.767 41.853 49.911 57.873 65.700 73.350

⫺9.835 ⫺7.963 ⫺3.811 4.394 11.222 18.710 26.549 34.574 42.662 50.713 58.663 66.473 74.104

⫺8.273 ⫺4.301 4.983 11.949 19.481 27.345 35.382 43.470 51.513 59.451 67.245 74.857

⫺8.561 ⫺4.777 5.646 12.681 20.256 28.143 36.190 44.278 52.312 60.237 68.015 75.608

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TABLE 11.58 Type J Thermocouples: Iron vs. Copper-Nickel Alloy Thermoelectric voltage in millivolts; reference junction at 0⬚C. 0

10

20

30

40

50

60

70

80

90

⫺200 ⫺100 ⫺0 0 100 200 300 400 500 600 700

⫺7.890 ⫺4.632 0.000 0.000 5.268 10.777 16.325 21.846 27.388 33.096 39.130

⫺8.096 ⫺5.036 ⫺0.501 0.507 5.812 11.332 16.879 22.397 27.949 33.683 39.754

⫺5.426 ⫺0.995 1.019 6.359 11.887 17.432 22.949 28.511 34.273 40.482

⫺5.801 ⫺1.481 1.536 6.907 12.442 17.984 23.501 29.075 34.867 41.013

⫺6.159 ⫺1.960 2.058 7.457 12.998 18.537 24.054 29.642 35.464 41.647

⫺6.499 ⫺2.431 2.585 8.008 13.553 19.089 24.607 30.210 36.066 42.283

⫺6.821 ⫺2.892 3.115 8.560 14.108 19.640 25.161 30.782 36.671 42.922

⫺7.122 ⫺3.344 3.649 9.113 14.663 20.192 25.716 31.356 37.280

⫺7.402 ⫺3.785 4.186 9.667 15.217 20.743 26.272 31.933 37.893

⫺7.659 ⫺4.215 4.725 10.222 15.771 21.295 26.829 32.513 38.510

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TABLE 11.59 Type K Thermocouples: Nickel-Chromium Alloy vs. Nickel-Aluminum Alloy Thermoelectric voltage in millivolts; reference junction at 0⬚C. 0

10

20

30

40

50

60

70

80

90

⫺200 ⫺100 ⫺0 0 100 200 300 400 500 600 700 800 900 1000 1100 1200 1300

⫺5.891 ⫺3.553 0.000 0.000 4.095 8.137 12.207 16.395 20.640 24.902 29.128 33.277 37.325 41.269 45.108 48.828 52.398

⫺6.035 ⫺3.852 ⫺0.392 0.397 4.508 8.537 12.623 16.818 21.066 25.327 29.547 33.686 37.724 41.657 45.486 49.129 52.747

⫺6.158 ⫺4.138 ⫺0.777 0.798 4.919 8.938 13.039 17.241 21.493 25.751 29.965 34.095 38.122 42.045 45.863 49.555 53.093

⫺6.262 ⫺4.410 ⫺1.156 1.203 5.327 9.341 13.456 17.664 21.919 26.176 30.383 34.502 38.519 42.432 46.238 49.916 53.439

⫺6.344 ⫺4.669 ⫺1.517 1.611 5.733 9.745 13.874 18.088 22.346 26.599 30.799 34.909 38.915 42.817 46.612 50.276 53.782

⫺6.404 ⫺4.912 ⫺1.889 2.022 6.137 10.151 14.292 18.513 22.772 27.022 31.214 35.314 39.310 43.202 46.985 50.633 54.125

⫺6.441 ⫺5.141 ⫺2.243 2.436 6.539 10.560 14.712 18.839 23.198 27.445 31.629 35.718 39.703 43.585 47.356 50.990 54.466

⫺6.458 ⫺5.354 ⫺2.586 2.850 6.939 10.969 15.132 19.363 23.624 27.867 32.042 36.121 40.096 43.968 47.726 51.344 54.807

⫺5.550 ⫺2.920 3.266 7.338 11.381 15.552 19.788 24.050 28.288 32.455 36.524 40.488 44.349 48.095 51.697

⫺5.730 ⫺3.242 3.681 7.737 11.793 15.974 20.214 24.476 28.709 32.866 36.925 40.879 44.729 48.462 52.049

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TABLE 11.60 Type N Thermocouples: Nickel– 14.2% Chromium– 1.4% Silicon Alloy vs. Nickel– 4.4% Silicon– 0.1% Magnesium Alloy Thermoelectric voltage in millivolts; reference junction at 0⬚C. 0

10

20

30

40

50

60

70

80

90

⫺200 ⫺100 ⫺0 0 100 200 300 400 500 600 700 800 900 1000 1100 1200 1300

⫺3.990 ⫺2.407 0.000 0.000 2.774 5.912 9.340 12.972 16.744 20.609 24.526 28.456 32.370 36.248 40.076 43.836 47.502

⫺4.083 ⫺2.612 ⫺0.260 0.261 3.072 6.243 9.695 13.344 17.127 20.999 24.919 28.849 32.760 36.633 40.456 44.207

⫺4.162 ⫺2.807 ⫺0.518 0.525 3.374 6.577 10.053 13.717 17.511 21.390 25.312 29.241 33.149 37.018 40.835 44.577

⫺4.227 ⫺2.994 ⫺0.772 0.793 3.679 6.914 10.412 14.091 17.896 21.781 25.705 29.633 33.538 37.402 41.213 44.947

⫺4.277 ⫺3.170 ⫺1.023 1.064 3.988 7.254 10.772 14.467 18.282 22.172 26.098 30.025 33.926 37.786 41.590 45.315

⫺4.313 ⫺3.336 ⫺1.268 1.339 4.301 7.596 11.135 14.844 18.668 22.564 26.491 30.417 34.315 38.169 41.966 45.682

⫺4.336 ⫺3.491 ⫺1.509 1.619 4.617 7.940 11.499 15.222 19.055 22.956 26.885 30.808 34.702 38.552 42.342 46.048

⫺4.345 ⫺3.634 ⫺1.744 1.902 4.936 8.287 11.865 15.601 19.443 23.348 27.278 31.199 35.089 38.934 42.717 46.413

⫺3.766 ⫺1.972 2.188 5.258 8.636 12.233 15.981 19.831 23.740 27.671 31.590 35.476 39.315 43.091 46.777

⫺3.884 ⫺2.193 2.479 5.584 8.987 12.602 16.362 20.220 24.133 28.063 31.980 35.862 39.696 43.464 47.140

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TABLE 11.61 Type R Thermocouples: Platinum– 13% Rhodium Alloy vs. Platinum Thermoelectric voltage in millivolts; reference junction at 0⬚C. 0

10

20

30

40

50

60

70

80

90

(Below zero) 0 100 200 300 400 500 600 700 800 900 1000 1100 1200 1300 1400 1500 1600 1700

0.0000 0.6472 1.4681 2.4000 3.4072 4.4706 5.5823 6.7412 7.9488 9.2034 10.5032 11.8463 13.2239 14.6239 16.0347 17.4447 18.8424 20.2151

⫺0.0515 0.0543 0.7228 1.5571 2.4978 3.5112 4.5796 5.6960 6.8598 8.0722 9.3313 10.6356 11.9827 13.3631 14.7647 16.1759 17.5852 18.9810 20.3497

⫺0.100 0.1112 0.8000 1.6471 2.5963 3.6157 4.6892 5.8101 6.9789 8.1960 9.4597 10.7684 12.1194 13.5025 14.9056 16.3172 17.7256 19.1194 20.4834

⫺0.1455 0.1706 0.8788 1.7381 2.6954 3.7208 4.7992 5.9246 7.0984 8.3203 9.5886 10.9017 12.2565 13.6421 15.0465 16.4583 17.8659 19.2575 20.6161

⫺0.1877 0.2324 0.9591 1.8300 2.7953 3.8264 4.9097 6.0398 7.2185 8.4451 9.7179 11.0354 12.3939 13.7818 15.1876 16.5995 18.0059 19.3953 20.7475

⫺0.2264 0.2965 1.0407 1.9229 2.8957 3.9325 5.0206 6.1554 7.3390 8.5703 9.8477 11.1695 12.5315 13.9218 15.3287 16.7405 18.1458 19.5329 20.8777

0.3627 1.1237 2.0167 2.9968 4.0391 5.1320 6.2716 7.4600 8.6960 9.9779 11.3041 12.6695 14.0619 15.4699 16.8816 18.2855 19.6702 21.0064

0.4310 1.2080 2.1113 3.0985 4.1463 5.2439 6.3883 7.5815 8.8222 10.1086 11.4391 12.8077 14.2022 15.6110 17.0225 18.4251 19.8071

0.5012 1.2936 2.2068 3.2009 4.2539 5.3562 6.5054 7.7035 8.9488 10.2397 11.5745 12.9462 14.3426 15.7522 17.1634 18.5644 19.9437

0.5733 1.3803 2.3030 3.3037 4.3620 5.4690 6.6230 7.8259 9.0758 10.3712 11.7102 13.0849 14.4832 15.8935 17.3041 18.7035 20.0797

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TABLE 11.62 Type S Thermocouples: Platinum– 10% Rhodium Alloy vs. Platinum

(McGHP)

Thermoelectric voltage in millivolts; reference junction at 0⬚C. 0

10

20

30

40

50

60

70

80

90

(Below zero) 0 100 200 300 400 500 600 700 800 900 1000 1100 1200 1300 1400 1500 1600 1700

0.0000 0.6453 1.4400 2.3227 3.2597 4.2336 5.2373 6.2743 7.3449 8.4483 9.5847 10.7536 11.9471 13.1550 14.3680 15.5765 16.7712 17.9417

⫺0.0527 0.0552 0.7194 1.5250 2.4143 3.3557 4.3327 5.3394 6.3799 7.4537 8.5605 9.7002 10.8720 12.0674 13.2762 14.4892 15.6967 16.8895 18.0562

⫺0.1028 0.1128 0.7948 1.6109 2.5065 3.4519 4.4320 5.4417 6.4858 7.5629 8.6730 9.8159 10.9907 12.1878 13.3975 14.6103 15.8168 17.0076 18.1698

⫺0.1501 0.1727 0.8714 1.6975 2.5991 3.5485 4.5316 5.5445 6.5920 7.6724 8.7858 9.9320 11.1095 12.3084 13.5188 14.7314 15.9368 17.1255 18.2823

⫺0.1944 0.2347 0.9495 1.7849 2.6922 3.6455 4.6316 5.6477 6.6986 7.7823 8.8989 10.0485 11.2286 12.4290 13.6401 14.8524 16.0566 17.2431 18.3937

⫺0.2357 0.2986 1.0287 1.8729 2.7858 3.7427 4.7318 5.7513 6.8055 7.8925 9.0124 10.1652 11.3479 12.5498 13.7614 14.9734 16.1762 17.3604 18.5038

0.3646 1.1089 1.9617 2.8798 3.8403 4.8323 5.8553 6.9127 8.0030 9.1262 10.2823 11.4674 12.6707 13.8828 15.9042 16.2956 17.4474 18.6124

0.4323 1.1902 2.0510 2.9742 3.9382 4.9331 5.9595 7.0202 8.1138 9.2403 10.3997 11.5871 12.7917 14.0041 15.2150 16.4148 17.5942

0.5017 1.2726 2.1410 3.0690 4.0364 5.0342 6.0641 7.1281 8.2250 9.3548 10.5174 11.7069 12.9127 14.1254 15.3356 16.5338 17.7105

0.5728 1.3558 2.2316 3.1642 4.1348 5.1356 6.1690 7.2363 8.3365 9.4696 10.6354 11.8269 13.0338 14.2467 15.4561 16.6526 17.8264

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TABLE 11.63 Type T Thermocouples: Copper vs. Copper-Nickel Alloy Thermoelectric voltage in millivolts; reference junction at 0⬚C. 0

10

20

30

40

50

60

70

80

90

⫺200 ⫺100 ⫺0 0 100 200 300 400

⫺5.603 ⫺3.378 0.000 0.000 4.277 9.286 14.860 20.869

⫺5.753 ⫺3.656 ⫺0.383 0.391 4.749 9.820 15.443

⫺5.889 ⫺3.923 ⫺0.757 0.789 5.227 10.360 16.030

⫺6.007 ⫺4.177 ⫺1.121 1.196 5.712 10.905 16.621

⫺6.105 ⫺4.419 ⫺1.475 1.611 6.204 11.456 17.217

⫺6.181 ⫺4.648 ⫺1.819 2.035 6.702 12.011 17.816

⫺6.232 ⫺4.865 ⫺2.152 2.467 7.207 12.572 18.420

⫺6.258 ⫺5.069 ⫺2.475 2.908 7.718 13.137 19.027

⫺5.261 ⫺2.788 3.357 8.235 13.707 19.638

⫺5.439 ⫺3.089 3.813 8.757 14.281 20.252

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CORRECTION FOR EMERGENT STEM OF THERMOMETERS

When a thermometer which has been standardized for total immersion is used with a part of the liquid column at a temperature below that of the bulb, the reading is low and a correction must be applied. The stem correction, in degrees Celsius, is given by KL(to ⫺ tm) ⫽ degrees Celsius where K ⫽ constant, characteristic of the particular kind of glass and temperature (see Table 11.49) L ⫽ length of exposed thermometer, ⬚C (that is, the length not in contact with vapor or liquid being measured) to ⫽ observed temperature on thermometer tm ⫽ mean temperature of exposed column (obtained by placing an auxiliary thermometer alongside with its bulb midpoint) For thermometers containing organic liquids, it is sufficient to use the approximate value, K ⫽ 0.001. In such thermometers the value of K is practically independent of the kind of glass.

TABLE 11.64 Values of K for Stem Correction of Thermometers Temperature, ⬚C

Soft glass

Heat-resistant glass

0– 150 200 250 300 350 400 450

0.000 158 0.000 159 0.000 161 0.000 164

0.000 165 0.000 167 0.000 170 0.000 174 0.000 178 0.000 183 0.000 188

short standard long

1 Index Terms Abbreviations: of amino acids, 3 letter and 1 letter of ligand names mathematical of SI units of states of aggregation of words ABS copolymers properties of Absolute configuration Absorbance: defined to percent absorption, table to transmittance, table Absorption bands, electronic, for chromophores Absorption cross section of nuclides Absorption edges, X-ray, wavelengths of Absorption indicators Absorption energies, X-ray, critical Absorption lines, atomic, of elements Absorption maxima, wavelengths, of acid-base indicators Absorption, percent, conversion to absorbance, table Absorptivity, defined Abundance, natural: of isotopes of nuclides Accuracy Acetal copolymers Acetal homopolymers Acetal polymers, properties of Acetals: nomenclature of as plastic materials, formulas and properties of Acetamide, binary azeotropes with Acetate, formation constants with Acetic acid: binary azeotropes with pKa values of ternary azeotropes with Acetone, binary azeotropes with pKa values in Acetonitrile: formation constances with pKa values in Acetylacetone, formation constants with Acetylene, solubility in water at various temperatures Acid anhydrides: infrared frequencies of nomenclature of Raman frequencies of

Links 11.102 3.11 2.23 2.3 2.6 2.26 10.20 10.50 1.49 7.39 2.96 2.98 7.19 4.58 7.8 11.95 7.7 7.29 8.116 2.96 7.38 4.81 4.59 7.89 2.118 10.8 10.22 10.8 10.22 10.22 1.23 10.8 10.22 5.74 8.88 5.63 8.81 5.80 5.74 8.81 8.88 8.81 8.88 5.3 7.50 1.23 7.78

2 Index Terms Acid-base indicators Acid-base titrations: indicators for primary standards for volumetric (titrimetric) factors for Acid chlorides, infrared frequencies of Acid dissociation constants: Harnmett and Taft equations for estimation of of indicators of inorganic materials of organic materials at various temperatures Acid halides: infrared frequencies of Raman frequencies of Acid halogenides Acid peroxides, infrared frequencies of Acid titrants, volumetric factors for Acid value: of fats and oils of waxes Acids: concentrations of commonly used functional derivatives of inorganic, nomenclature of inorganic, nomenclature of organic, nomenclature of standardization of basic solutions trivial names for inorganic (table) Acrylic poly(vinyl chloride) alloy, properties of Acrylic polymers: description of properties of Acrylonitrile-butadiene-styrene (ABS) copolymers AcryIonitrile- butadiene-styrene-poly ( vinyl chloride ) alloy, properties of Activity coefficients at high ionic strengths Acyclic conformation isomers Acyl halides, nomenclature of Acylals, nomenclature of Addition compounds, nomenclature of Additives to polymers Adjusted retention time Adsorption indicators Affinities, electron: of atoms of molecules of radicals Affixes, multiplying

Links 8.115 8.116 11.74 11.76 7.50

9.2 8.116 8.18 8.24 8.73 7.50 7.78 3.8 7.50 11.76 10.69 10.72 11.106 3.8 3.8 1.29 11.75 3.8

1.38

10.24 10.8 10.8 10.24 10.19 10.24 8.2 8.5 1.39 1.24 1.23 3.112 10.4 11.27 11.95 4.24 4.25 4.27 1.21

3 Index Terms

Links

Aggregation, states of, abbreviations for Air: autoignition temperatures of combustible mixtures buoyancy reduction factor for weighings flammable limits of combustible mixtures in moist, density of refractive index of saturated, mass of water vapor in at various temperatures solubility in water at various temperatures specific gravity at various temperatures Alcoholometer Alcohols: binary azeotropes with nomenclature of retained trivial names of ternary azeotropes with Aldehydes: binary azeotropes with infrared frequencies of nomenclature of Raman frequencies of Alicyclic ring systems, carbon-13 chemical shifts Aliphatic hydrocarbons, monocyclic, nomenclature of Alizarin red, formation constants with Alkali titrants, volumetric factors for Alkane carbon-hydrogen and carbon-carbon bonds Raman frequencies of Alkane carbons, estimation of carbon-13 chemical shifts Alkane residues, infrared frequencies of Alkanes: carbon-13 chemical shifts nomenclature of proton chemical shifts Raman frequencies of Alkenes: carbon-13 chemical shifts infrared frequencies of nomenclature of proton chemical shifts Raman frequencies of Alkyd molding polymers, properties of Alkyd polyester thermosetting polymers, properties of Alkyd polymers Alkyl carbon-13 chemical shifts, effect of substituents upon Alkyl groups, effects of substituent groups on carbon-13 chemical shifts

2.7

5.139 2.83 5.139 5.88 5.135 5.156 5.3 5.88 2.66 5.57 1.24 1.24 5.81

5.66

5.59 7.51 1.26 7.78 7.101 1.5 8.89 11.77

7.71 7.102 7.41 7.102 1.1 7.92 7.71 7.103 7.54 1.4 7.92 7.79 10.24 10.42 10.42 10.9 7.102 7.102

4 Index Terms

Links

Alkynes, nomenclature of Allotropes Alloy polymers: description of properties of Allyl alcohol: binary azeotropes with ternary azeotropes with Allyl polymers: description of properties of Allyl-diglycol-carbonate polymer, properties of Alphabet, Greek Alternate names of organic compounds Alternative hypothesis Altitude-gravity correction in barometry Altitude-temperature factor in barometry Alumina, solvent strength parameters Aluminum: bond dissociation energies gravimetric factors Amides: infrared frequencies of inorganic nomenclature of Amidines, infrared frequencies of Amines: binary azeotropes with infrared frequencies of nomenclature of Amino acids, pI and pKa values Ammonia: formation constants with liquid, vapor pressure of solubility in water at various temperatures Ammoniameter Ammonium compounds: gravimetric factors nomenclature of Ammonium ion, infrared frequencies of Amorphous polymers Amount of substance Ampere, definition of Analytical reagents for gravimetry Analytical weights, tolerances for Analyzing crystals, for X-ray spectroscopy Angle, trigonometric functions of Angles in unit cells Anhydrides, of inorganic acids Aniline, binary azeotropes with Animal fats and oils, properties of Anion-exchange resins, guide to (table)

1.4 3.5 10.10 10.24 5.71 5.78 10.10 10.26 10.26 2.25 1.74 2.126 2.77 2.78 11.16

1.76

4.41 11.41 7.52 3.9 1.27 7.54 5.59 7.41 1.27 11.102 8.83 5.27 5.3 2.66 11.41 1.28 7.46 10.2 2.3 2.3 11.67 11.71 7.13 2.113 2.115 4.58 3.9 5.75 10.69 11.33

5 Index Terms Anions, inorganic: nomenclature of selectivity coefficients in ion exchange Anomalous electron moment correction Antifreeze solutions, aqueous Antimony: bond dissociation energies gravimetric factors Antioxidants for polymers Antistatic agents for polymers Antoine equation Aqueous tension of solutions Aramid polymer, properties of Areas: between abscissa values of normal distribution curve by approximation of surfaces Argon, solubility in water at various temperatures Argon ICP, detection limits of elements (table) Argon-ion laser plasma lines Arithmetic means of set of numbers Arithmetic mean Aromatic bands, infrared frequencies of Aromatic compounds: carbon-13 chemical shifts monocyclic, nomenclature of proton chemical shifts Raman frequencies of Aromatic nylon polymer, properties of Aromatic polyester polymers, properties of Arsenazo, formation constants with Arsenic: bond dissociation energies gravimetric factors Astatine bond dissociation energy Atmospheres, conversion to other pressure units Atom radius of an element Atomic absorption: electrothermal, detection limits of elements to flame, detection limits of elements Atomic and group refractions (table) Atomic fluorescence, plasma, detection limits of elements Atomic mass constant Atomic number of elements Atomic quantities, symbols, SI units and definitions Atomic refractions Atoms, electron affinities of

Links 3.6 11.38 2.4 5.83

3.10

4.41 11.42 10.4 10.4 5.29 11.6 10.38

2.122 2.111 2.109 5.8 7.29 7.88 2.118 2.118 7.57 7.104 7.105 1.5 7.96 7.82 10.38 10.42 8.89 4.41 11.43 4.41 2.87 4.29

7.29 7.29 5.136 7.29 2.4 4.2 2.6 5.135 4.24

6 Index Terms Aurintricarboxylic acid, formation constants with Autoignition temperature of combustible mixtures in air Average linear velocity of mobile phase Avogadro number constant Axes in unit cells Azeotropic mixtures: binary ternary Azo compounds: infrared frequencies of nomenclature of Raman frequencies of Azoxy compounds: infrared frequencies of nomenclature of Balling hydrometer Band asymmetry Barium: bond dissociation energies gravimetric factors Barkometer (barktrometer) Barometric corrections: for capillarity for latitude-gravity reduction to sea level for temperature Barometry Base width of chromatographic peak Bases: concentration of commonly used primary standards for aqueous acidic solutions Bates brewers' saccharometer Bates-Guggenheirn convention for pH Baume degrees, conversion to density Baume hydrometers Beck's hydrometer Beer's law Beilstein's Handbuch references for organic compounds Benzene: absorption bands (ultraviolet) of binary azeotropes with carbon-13 chemical shifts in substituted proton chemical shifts in monosubstituted Raman frequencies of substitution patterns vapor permeability of polymers Benzene ring, substitution patterns, Raman frequencies

Links 8.89 5.139 11.27 2.4 5.169 4.58 5.58 5.77 7.55 1.28 7.81 7.55 1.28 2.68 11.28 4.41 11.43 2.66 2.71 2.75 2.78 2.72 2.7 11.29

2.75

11.106 11.74 2.68 8.115 2.85 2.67 2.67 7.39 1.74 7.23 5.76 7.104 7.96 7.82 10.69 7.83

1.76

7 Index Terms Benzoylacetone, formation constants with Benzyl alcohol, binary azeotropic mixtures Berthelot's equation of state Beryllium: bond dissociation energies gravimetric factors Best-fit line errors in slope and intercept Binary azeotropes containing alcohols containing ketones containing organic acids containing water Binary compounds between nonmetals Biological buffers, pH range Biological materials, pH measurement of Bis(2-hydroxyethyl) ether, binary azeotropes with Bismuth: bond dissociation energies gravimetric factors Bisphenol epoxy resin, properties of Bivalent sulfur, nomenclature of Blackbody radiation Blaze wavelength Block copolymers of styrene, properties of Blood, pH measurement of Body-centered cubic structure Bohr magneton Bohr radius Boiling point: of chromatographic solvents of inorganic compounds molecular elevation of of organic compounds organic solvents arranged by of water at various pressures Boiling point temperature, calculation of Boltzmann constant Bond dipole moments Bond dissociation energies Bond lengths and strengths (See also entries for specific elements) Bonds, spatial orientation of Borate, reference pH buffer solution at various temperatures Boron: bond dissociation energies bond lengths with other elements gravimetric factors Boron compounds: infrared frequencies of nomenclature of

Links 8.89 5.71 5.170 4.41 11.44 2.133 2.135 5.58 5.66 5.74 5.62 5.58 3.2 8.110 8.106 5.76 4.42 11.44 10.28 1.37 7.38 7.40 10.3 10.54 8.106 4.57 2.4 2.4 11.16 3.14 11.13 1.76 11.10 5.56 5.30 2.4 4.53 4.41 4.29 4.56 8.105 4.42 4.39 11.44 7.61 1.29

7.39

8 Index Terms Boron-11 chemical shifts Boyle's law Branched polymers BR rubber Bragg equation Bridged hydrocarbons, nomenclature of Briggsian system of logarithms Brix hydrometer Bromide, formation constants with Bromine: bond dissociation energies gravimetric factors overpotential of solubility in water at various temperatures Buffer solutions: for control purposes standard reference Buna N rubber Buna S rubber Buoyancy effect when weighing in air Burets, tolerances for Burning rate of polymers Butadiene-maleic acid copolymer, properties of 1-Butanol: binary azeotropes with ternary azeotropes with 2-Butanol, ternary azeotropes with 2-Butanone, binary azeotropes with 2-Butoxyethanol, binary azeotropes with Butyl rubber Butyric acid, binary azeotropes with Cadmium: bond dissociation energies gravimetric factors Calcium: bond dissociation energies gravimetric factors Calcium chloride solutions, percent humidity of Calcium hydroxide reference pH buffer solution at various temperatures Calibration of conductivity vessels Calmagite, formation constants with Calomel reference electrodes, EMF as function of temperature Candela, definition of Capacity factor (see Partition ratio) Capillarity correction for barometer Carbon: attached to double bond, estimation of chemical shifts of bond dissociation energies gravimetric factors

Links 7.111 5.169 10.3 10.59 7.40 1.10 2.102 2.67 8.84 4.42 11.44 8.140 5.3 8.110 8.104 10.59 10.61 2.83 11.103 10.22 10.42 5.69 5.78 5.78 5.74 5.72 10.60 5.64

4.42 11.44 4.42 11.45 11.7 8.105 8.160 8.90 8.113 2.3 2.75

7.103 4.42 11.46

2.68

9 Index Terms Carbon-carbon: bond lengths single bonds, Raman frequencies of spin coupling constants Carbon dioxide: gas permeability of polymers and rubbers solubility in water at various temperatures Carbon-fluorine spin coupling constants Carbon-halogen bond lengths Carbon-hydrogen: bond lengths infrared absorption frequencies Raman frequencies spin coupling constants Carbon-metals bond lengths Carbon monoxide solubility in water at various temperatures Carbon-nitrogen, bond lengths Carbon-nitrogen bonds, Raman frequencies of Carbon-nitrogen double bonds, Raman frequencies of Carbon-nitrogen spin coupling constants Carbon-oxygen bond lengths Carbon-selenium bond lengths Carbon-silicon bond lengths Carbon-sulfur bond lengths Carbon tetrachloride vapor permeability for polymers Carbon-13: alkanes, estimation of chemical shifts of attached to double bond, estimation of chemical shifts chemical shifts of carbonyl groups in substituted benzenes in substituted pyridines Carbon-13 spin coupling constants Carbonate reference pH buffer solution at various temperatures Carbonyl groups: carbon-13 chemical shifts infrared frequencies of Raman frequencies of Carboxylate ions, Raman frequencies of Carboxylic acids: infrared frequencies of nomenclature of Raman frequencies of Carter's hydrometer Cations exchange resins for (guide) inorganic, nomenclature of relative selectivity in ion exchange

Links

4.36 7.75 7.108 10.66 5.4 7.109 4.36 4.37 7.41 7.71 7.107 4.38 5.4 4.37 7.74 7.77 7.116 4.37 4.38 4.38 4.38 10.69 7.102 7.103 7.99 7.106 7.104 7.105 7.107 8.105 7.106 7.5 7.78 7.79 7.52 1.29 7.79 2.67 11.34 3.6 11.37

7.80

10 Index Terms Cellulose acetate polymers: description of properties of Cellulose-acetate-butyrate polymer: description of properties of Cellulose-acetate-propionate polymer: description of properties of Cellulose nitrate polymer: description of properties of Cellulose triacetate Cellulosic polymers: description of properties of Celsius to Fahrenheit conversion factors Centered period, use of Centistokes, conversion factors Cerium: bond dissociation energies equations and equivalents for gravimetric factors Cesium: bond dissociation energies gravimetric factors Chain compounds, formulas for Chain-transfer agents for polymers Characteristic of a common logarithm Characteristic low-mass neutral fragments from the molecular ion Charge numbers in inorganic formulas Charge-to-mass ratio for electron Charles' law Chemical Abstracts indexing system Chemical blowing agents for polymers Chemical nomenclature: inorganic organic Chemical reactions, symbols, SI units and definitions Chemical resistance: or polymers of rubbers Chemical shifts: of boron-11 of carbon-13 attached to a double bond in carbonyl groups in substituted benzenes in substituted pyridines of fluorine-19 of nitrogen-15 of phosphorus-31

Links 10.10 10.26 10.11 10.26 10.11 10.28 10.11 10.28 10.10 10.10 10.26 2.54 3.2 2.82 4.43 11.66 11.47 4.44 11.47 3.2 10.4 2.102 7.127 3.4 2.4 5.169 1.49 10.6 3.1 1.2 2.7 10.64 10.65 7.111 7.99 7.103 7.106 7.104 7.105 7.117 7.112 7.119

11 Index Terms Chemical shifts: (Cont.) of protons in methine and methylene groups, estimation of of protons, in monosubstituted benzene of residual protons in incompletely deuterated solvents of silicon-29 Chemical structures: of crystals of ion-exchange resins of polymers of rubbers Chemical symbols and definitions Chemicals: common reactive and incompatible flammable recommended for refrigerated storage which polymerize or decompose on extended refrigeration Chi square distribution percentiles of Chiral compounds, sequence rules for Chirality and optical activity Chloride, formation constants with Chlorinated polyester polymer, properties of Chlorinated poly(vinyl chloride), properties of Chlorine: bond dissociation energies gravimetric factors overpotential of solubility in water at various temperatures Chlorosulfonated polyethylene Chromatographic behavior of solutes Chromatographic solvents Chromatography, symbols and definitions for Chromium: bond dissociation energies gravimetric factors Chromophores, electronic absorption bands for Circle, properties of Citrate reference pH buffer solution at various temperatures Citric acid, formation constants with Clapeyron equation Clausius-Clapeyron equation Cleaning solutions for fritted glassware Cobalt: bond dissociation energies gravimetric factors Coefficient of linear expansion, of polymers Coefficient of variation, in statistics Coefficient of viscosity

Links

7.94 7.96 7.98 7.118 4.58 11.32 10.8 10.58 10.58 2.6 11.130 11.136 11.136 11.136 2.128 2.129 1.44 1.45 8.83 10.28 10.56 4.44 11.47 8.140 5.4 10.58 11.27 11.16 2.8 4.44 11.47 7.19 2.110 8.105 8.90 6.3 6.3 11.69 4.33 11.48 10.22 2.114 5.137

12 Index Terms

Links

Collective inorganic names Colloid chemistry, symbols, SI units, and definitions for Colloids, protective Column efficiency Column selectivity factor (see Relative retention) Combustible mixtures in air Commercial plastics, properties of Common logarithms Complexometric titrations indicators for Compressibility factor, in gas chromatography critical Compressibility of water Compressive modulus of polymers Compressive strength, rupture, of polymers Compton wavelength of electron, neutron, and proton Conductance of electrolyte solution, defined relations in Conductivities, equivalent, of electrolytes in aqueous solutions Conductivity: defined equivalent electrical, of various pure liquids of standard potassium chloride solutions of water at various temperatures Conductivity, thermal: of elements of gases at various temperatures of liquids at various temperatures of solids Cone, volume and area of Confidence level and limits Configuration, electronic, of elements Conformational isomers Conjunctive nomenclature Constants, fundamental Control charts Conversion factors temperature Cooling mixtures Coordination bonds, dipole moments Coordination compounds, inorganic nomenclature of Copolymerization Copper: bond dissociation energies gravimetric factors Copper vs. copper-nickel alloy thermocouple

3.4 2.10 11.95 11.27

5.139 10.22 2.102 11.89 11.96 11.26 6.134 5.156 10.22 10.22 2.4 8.157 8.169 8.168 8.163 8.168 8.169 8.161 8.160 8.168 4.2 5.148 5.151 5.154 2.112 2.124 4.2 1.39 1.21 2.117 2.137 2.35 2.54 11.3 4.54 3.10 10.3 4.44 11.49 11.140 11.149

13 Index Terms Correction for solvents in ultraviolet-visible region Coupling agents for polymers Covalent radii of elements Critical compressibility factor, defined Critical density Critical phenomena Critical pressure of elements and compounds Critical temperature, of elements and compounds Critical volume, of elements and compounds Critical X-ray absorption energies Cross-linked polymer, defined Cross section, thermal neutron absorption, of nuclides Crucibles used for fusions Cryoscopic constants Crystal lattice types Crystalline polymers Crystal structures, in inorganic nomenclature Crystals, analyzing, for X-ray spectroscopy Cube, area and volume of Cubic crystal lattices Cubical coefficients of thermal expansion Cumulated double bonds: infrared frequencies of Raman frequencies of Curium, bond dissociation energy Curve fitting Cyanato type compounds, nomenclature of Cyanide, formation constants with Cyclic compounds, conformations of Cyclic hydrocarbons with side chains, nomenclature of Cyclic ring systems: carbon-13 chemical shifts in nitrogen-15 chemical shifts in proton chemical shifts in Cyclohexanol, binary azeotropes with Cylinder, volume and area of Dalton's law of partial pressures Dative bonds, dipole moments Debye-Hückel equation Decay of radionuclides Definitions of physical and chemical quantities Deflection temperature of polymers under flexural load Degree Celsius (see Celsius to Fahrenheit conversion factors)

Links 7.23 10.4 4.35 6.143 6.143 6.142 6.142 6.142 6.141 6.142 7.8 10.3 4.59 11.70 11.4 4.57 10.2 3.10 7.15 2.112 4.57 11.105 7.49 7.77 4.44 2.133 1.36 8.84 1.41 1.11 7.100 7.113 7.93 5.70 2.112 5.170 4.54 8.2 4.59 2.6 10.22

8.5

14 Index Terms Degree Fahrenheit (see Fahrenheit to Celsius conversion factors) Degree kelvin Degree of ionic character of bonds Degrees of freedom, in statistics Deionizer, in flame photometry Demasking Demasking agents (table) Density: of aqueous glycerol solutions conversion to degrees Baumé and Twaddell critical determined, with pyknometer with plummet or sinker of elements hydrometers and relation between scales of inorganic compounds of mercury of moist air of organic compounds of solvents and specific gravity of sucrose solutions of water Derivatives and differentiation Desiccants Detection limits, atomic absorption and atomic emission Determinative errors Deuterated solvents, chemical shifts: of carbon-13 of residual protons Deuterium oxide, vapor pressure of Dew point readings and relative humidity Diallyl phthalate molding polymers, properties of Diallyl phthalate polymers Diamagnetic shielding factor, spherical water molecule 1,2-Diarninocyclohexane-N,N,N',N'-tetraacetic acid formation constants with Diastereomers Diatomic molecules: binding energies of bond lengths Dibenzoylmethane, formation constants with Dichromate, volumetric factors for Dielectric constant: discussion of of inorganic compounds of organic compounds of water at various temperatures of polymers

Links

2.3 4.29 2.123 7.41 11.93 11.100 5.138 2.85 6.143 5.89 5.89 3.12 2.66 3.12 5.87 5.88 1.76 11.18 2.66 5.138 5.85 2.104 11.5 7.29 2.118 7.110 7.98 5.30 11.9 10.26 10.10 2.4 8.90 1.39 4.41 4.29 8.91 11.79 5.137 5.130 5.105 5.134 10.22

5.87

15 Index Terms

Links

Dielectric strength of polymers Dienes, absorption maxima of Dienones, absorption wavelength of Differentiation, rules for 4,5-Dihydroxybenzene-1,3-disulfonic acid, formation constants with Dimensionless quantities, symbols and definitions 2,3-Dimercaptopropan-1-of, formation constants with Dimethylglyoxime, formation constants with Dimethylsulfoxide, pKa values in Dipole moments discussion of of inorganic compounds of organic compounds 2,2-Dipyridyl, formation constants with Dispersion of data, measures of Dissipation (power) factor of polymers Dissociation energy of diatomic molecules Distribution coefficient in ion exchange Distribution curve, normal Distribution of measurements Distribution ratio, symbols and definitions for Double bonds: cumulated: infrared frequencies of Raman frequencies of estimation of chemical shift of protons attached infrared red frequencies of protons attached, estimation of chemical shift Raman frequencies of Double-bond radii, of elements Drying agents Drying and humidification Duane-Hunt equation Durometer hardness of rubbers Dynamic viscosity Dysprosium, bond dissociation energies

10.22 7.19 7.22 2.104

Ebullioscopic constants ED PM rubber EDTA complex, formation constants of EDTA, values of α4 at various pH values Effective ionic radii in aqueous solutions Effective plate number Einstein equation Elastomeric fibers Elastomers, defined Electric quadrupole moment of elements Electrical conductivity of pure liquids Electrical properties of polymers

11.13 10.60 11.97 11.97 8.4 11.28 7.38 10.18 10.2 7.89 8.161 10.22

8.91 2.22 8.92 8.92 8.81 4.53 5.136 5.130 5.105 8.92 2.121 10.22 4.41 11.39 2.119 2.118 2.8

7.49 7.77 7.95 7.49 7.95 7.79 4.35 11.5 11.5 7.39 10.63 5.137 4.44

16 Index Terms Electrical resistivity of elements Electric current Electricity, symbols, SI units, and definitions Electrochemistry, symbols, SI units, and definitions Electrode potentials Electrodes, reference, potential of Electrolytes, equivalent conductivities in aqueous solutions Electromagnetic radiation symbols, SI units, and definitions for Electrometric measurement of pH Electron affinities, of elements, molecules, and radicals Electron magnetic moment Electron radius, classical Electron rest mass Electronegative constituents, in inorganic formulas Electronegativity of elements (table) Electronic absorption bands for chromophores Electronic configuration of elements Electrothermal atomic absorption, detection limits of elements Elementary charge Elements: abundance of naturally occurring isotopes atom radius of atomic number of density of effective ionic radii electrical resistivity of electron affinities of electronegativities of electronic configuration and properties ionization energy isotopes of naturally occurring linear thermal expansion of magnetic moment of names and symbols for nuclear properties of potentials of quadrupole moment of sensitive emission limes of standard stock solutions symbols of thermal conductivity of work functions of X-ray filters for Ellipse, area of Ellipsoid, area and volume of Elongation, at break of polymers ultimate, of rubbers

Links 4.2 2.3 2.11 2.12 8.124 8.113 8.163 7.38 2.13 8.115 4.24 2.4 2.4 2.4 3.3 4.28 4.29 7.19 4.2 7.29 2.4 4.81 4.29 4.2 3.12 4.30 4.2 4.24 4.29 4.1 4.6 4.81 4.2 7.89 3.3 4.42 8.124 7.89 7.34 11.107 4.2 4.2 4.80 7.14 2.111 2.113 10.22 10.60

7.89

17 Index Terms Emergent stem correction of thermometers Emission energies, X-ray Emission limits of elements Emission spectra, X-ray Emission wavelengths, of fluorescent compounds Empirical formula index of organic compounds Enantiomers Enclosing marks, use in inorganic formulas Energy equivalents Energy of ionization of molecular and radical species Engler degrees Enones, absorption wavelength of Enthalpies: of inorganic compounds of organic compounds Enthalpy: of formation of ions of melting: of inorganic compounds of organic compounds of sublimation of inorganic compounds of organic compounds of a system of vaporization of inorganic compounds of organic compounds Enthalpy change of bonds (see Bond dissociation energies) Entropies: of inorganic compounds of melting of organic compounds of sublimation of vaporization Entropy of a system Epichlorohydrin rubber Epoxy casting resins, properties of Epoxy polymers Epoxy resins, properties of Epoxy silicone polymers, properties of Equations of state for real gases Equivalent conductances: of hydrogen ion at various temperatures of hydroxyl ion at various temperatures Equivalent conductivity: defined of electrolytes in aqueous solutions Equivalent ionic conductances, limiting

Links 11.150 7.10 7.29 7.3 7.25 1.58 1.46 3.2 2.4 4.8 2.82 7.22 6.81 6.5 6.2 4.8 6.124 6.51 6.3 6.124 6.51 6.4 6.3 6.124 6.51

6.81 6.4 6.5 6.4 6.4 6.5 10.59 10.30 10.11 10.28 10.48 5.170 8.168 8.168 8.169 8.163 8.157

6.51

18 Index Terms Equivalent weights for redox determinations (See also Titrimetric factors) Erbium, bond dissociation energies gravimetric factors Eriochrome Black T, formation constants with Error curve Error probability, in statistics Errors in quantitative analysis Esters: binary azeotropes with infrared frequencies of of inorganic acids nomenclature of Raman frequencies of Ethane, solubility in water at various temperatures 1,2-Ethanediol, binary azeotropes with 1,2-Ethanediol monoacetate, binary azeotropes with Ethanol: binary azeotrop es with pKa values in ternary azeotropes with vapor permeability for polymers Ethanolamine, formation constants with Ethanol-water mixtures, freezing point of Ethers: binary azeotropes with infrared frequencies of Raman frequencies of 2-Ethoxyethanol, binary azeotropes with Ethyl acetate, vapor permeability for polymers Ethyl cellulose polymer: description of properties of Ethylene, solubility in water at various temperatures Ethylene-chlorotrifluoroethylene copolymer: description of properties of Ethylene glycol-water mixtures, freezing point of Ethylene-propylene-diene rubber Ethylene-tetrafluoroethylene copolymer Ethylene-vinyl acetate copolymer, properties of Ethylenediamine, formation constants with Ethylenediamine-N,N,N',N'-tetraacetic acid, formation constants with Ethylenediaminetetraacetic acid, values of α4 at various pH Europium, bond dissociation energies

Links 11.84 4.45 11.49 8.92 2.119 2.123 2.118 5.59 7.50 3.9 1.36 7.78 5.4 5.72 5.73 5.66 8.81 5.77 10.69 8.93 5.83 5.61 7.58 7.85 5.72 10.69 10.11 10.28 5.4 10.13 10.32 5.84 10.60 10.13 10.44 8.93 8.93 11.91 4.45

19 Index Terms Excitation wavelengths of fluorescent compounds Expansion in series Explosive limits of combustible mixtures in air Exponential series Eykrnan equation F statistic (tables) F test for equality of variances Face-centered lattices Fahrenheit to Celsius conversion factors Faraday constant Fats, properties of Fatty oil hy drometer Fehling's solution Filters, membrane for X-rays Fine structure constant First radiation constant Flame atomic absorption, detection limits of elements Flame emission, detection limits of elements Flame retardants for polymers Flammable chemicals Flammable limits of combustible mixtures in air Flash point of organic compounds Flasks, volumetric, tolerances for Flexural modulus of polymers Flexural strength, rupture, of polymers Fluidity, definition of Fluorescence laws of plasma atomic, detection limits of elements quantum yield values standards Fluorescent compounds, excitation and emission wavelengths Fluorescent indicators for acid-base titrations Fluoride, formation constants with Fluorinated ethylene-propylene resin: description of properties of Fluorine: bond dissociation energies equations and equivalents for gravimetric factors Fluorine-carbon spin coupling constants Fluorine-19 to fluorine-19 spin coupling constants Fluorine-19 chemical shifts

Links 7.25 2.115 5.139 2.115 5.135 2.131 2.130 4.57 2.54 2.5 10.69 2.67 11.114 11.70 7.132 2.5 2.5 7.29 7.29 10.5 11.115 5.139 1.76 11.102 10.22 10.22 5.133 7.25 7.38 7.29 7.28 7 .28 7.25 8.120 8.84 10.12 10.32 4.45 11.68 11.49 7.109 7.118 7.117

20 Index Terms Fluorocarbon polymers: description of properties of Fluxes for sample decomposition Foaming agents for polymers Foams, polyurethane Formation, enthalpy of Formation constants of metal complexes with inorganic ligands with organic ligands Formic acid, binary azeotropes with Formula weights: of inorganic compounds of organic compounds Formulas: of inorganic compounds of organic compounds of plastic materials writing, of inorganic compounds (See also Nomenclature) Fortin barometer Fourier's series Fragmentation patterns in mass spectrometry Free radicals, writing formula for Freedom, degrees of, in statistics Freezing mixtures Freezing point, molecular lowering of Frequency, defined Fritted glassware: cleaning solutions for pore sizes of Functional class names in radicofunctional nomenclature Functional groups, in ion-exchange resins nomenclature of Functional organic compounds, nomenclature of Fundamental physical constants Fused polycyclic hydrocarbons, nomenclature of Fusion, heats of (see Heats of melting) g factor (Landé) for free electron Gadolinium, bond dissociation energies gravimetric factors Gallium, bond dissociation energies Gas (ideal), molar equivalent at various pressures and temperatures Gas chromatography: McReynolds' constants stationary phases Gas constant

Links 10.12 10.30 11.70 10.5 10.18 6.2 8.82 8.83 8.88 5.62 3.14 1.76 3.14 1.76 10.8 10.58 3.1 2.70 2.116 7.126 3.2 2.123 5.83 11.4 7.38 11.69 11.71 1.22 11.32 1.23 1.17 2.3 1.6

2.5 4.45 11.50 4.27 2.88 11.21 11.21 2.5

11.3

21 Index Terms Gases: equations of state for permeability constants of polymers and rubbers physical chemistry equations for reduction to standard temperature and pressure solubility in water at various temperatures thermal conductivities at various temperatures Van der Waals' constants velocity of Gaussian distribution curve Geometric mean of set of numbers Geometrical isomerism Geometrical isomers, sequences rules for Geometry, molecular Germanium, bond dissociation energies gravimetric factors Gibbs energies of formation: of inorganic compounds of organic compounds Glycerol-water mixtures: density and viscosity of freezing point of Glycine, formation constants with Gold, bond dissociation energies gravimetric factors Graft copolymers Graham's law of diffusion, of gases Grating equation Gravimetric analysis, reagents for Gravimetric factors Gravitational constant Gravity-latitude corrections for barometer Greek alphabet GRN rubber Group dipole moments Group refractions Gutta percha Hafnium, bond dissociation energies Haggenmacher equation Half-lives, of nuclides Half-wave potentials, voltarnmetric: of inorganic materials of organic materials Haloalkanes, Raman frequencies of Halogen compounds: infrared frequencies of Raman frequencies of Halogen-carbon bond lengths Halogen derivatives (organic), nomenclature of

Links 5.170 10.66 5.169 2.91 5.3 5.148 5.157 5.171 2.119 2.118 2.119 1.43 1.44 4.56 4.45 11.50 6.81 6.5 5.138 5.85 8.94 4.45 11.50 10.3 5.171 7.40 11.67 11.41 2.4 2.75 2.25 10.59 4.54 5.136 10.58 4.45 6.3 4.59 8.141 8.146 7.80 7.62 7.86 4.36 1.31

22 Index Terms Halogenated hydrocarbons, binary azeotropes with Hammett equation Hammett substituent constants Hardness: of polymers of rubbers Hartree energy Heat capacities: of inorganic compounds of organic compounds Heat capacity of any phase Heating baths Heating temperatures of precipitates Heats of fusion (see Heats of melting) Heats of melting: of inorganic compounds of organic compounds Heats of sublimation: of inorganic compounds of organic compounds Heats of vaporization: of inorganic compounds of organic compounds Helium: gas permeability of polymers and rubbers solubility in water at various temperatures Henry's law for gases Heteroaromatics, primary absorption bands of Heteroatomic inorganic anions, nomenclature of Heterocyclic rings: carbon-13 chemical shifts proton chemical shifts, in saturated in unsaturated Raman frequencies of Heterocyclic systems, nomenclature of Hexagonal crystal lattice Hexane, vapor permeability for polymers High-density polyethylene, properties of High performance liquid chromatography Hittorf transport numbers HPLC, typical performances Humidity, relative: from dew points from wet and dry bulb thermometer readings Humidity, solutions for maintaining constant Hybrid bonds Hydrocarbon ring assemblies, nomenclature of Hydrocarbons: binary azeotropes with halogenated, binary azeotropes with

Links 5.59 9.2 9.2 10.22 10.63 2.5 6.81 6.124 6.5 6.51 6.3 11.15 11.72

6.124 6.51 6.124 6.51 6.124 6.51 10.66 5.8 5.172 7.23 3.5 7.100 7.101 7.93 7.94 7.87 1.11 4.57 4.58 10.69 10.44 11.30 8.169 11.31 11.9 11.8 11.6 4.56 1.10 5.61 5.59

11.7

23 Index Terms Hydrogen: binary inorganic compounds, nomenclature of bond dissociation energies bond lengths with other elements gas permeability of polymers and rubbers gravimetric factors infrared frequencies of single bonded overpotential of solubility in water at various temperatures Hydrogen-carbon: bond lengths single bonds, infrared frequencies of Raman frequencies of spin coupling constants Hydrogen bromide, solubility in water at various temperatures Hydrogen chloride, solubility in water at various temperatures Hydrogen ion, equivalent conductance at various temperatures (See also pH) Hydrogen-nitrogen, infrared absorption frequencies spin coupling constants Raman frequencies Hydrogen overpotential Hydrogen sulfide, solubility in water at various temperatures Hydrometer conversion table Hydrometers Hydroxide, formation constants with N-(2-Hydroxyethyl)ethylenediarnineN,N,N'-triacetic acid, formation constants with 6-Hydroxy -2-methylquinoline, formation constants with Hydroxyl group: infrared frequencies of Raman frequencies of Hydroxyl ion, equivalent conductance at various temperatures Hydroxylarnines, nomenclature of 8-Hydroxyquinoline-5-sulfonic acid, formation constants with Hypotheses about means Ice, vapor pressure of ICP, detection limits of elements Ignition temperature, (see Autoignition) Imides, infrared frequencies of Imines: infrared frequencies of nomenclature of

Links

3.5 4.46 4.39 10.66 11.50 7.42 8.140 5.4 4.37 7.41 7.71 7.107 7.108 5.8 5.8 8.168

7.46 7.122 7.74 8.140 5.6 2.85 2.66 8.84 8.95 8.95 7.44 7.74 8.168 1.31 8.95 2.126 5.26 7.29 7.53 7.46 1.32

7.54

24 Index Terms Impact strength (Izod) of polymers Inches mercury, conversion to other pressure units Inches water, conversion to other pressure units Incompatible and reactive chemicals Indeterminate errors Indicators: for acid-base titrations for complexometric titrations for oxidation-reduction titrations preparation of Indium, bond dissociation energies gravimetric factors Induction coupled plasma, detection limits of elements Inductive effect of a substituent Infrared spectroscopy Infrared transmission characteristics of solvents Infrared transmitting materials Inhibitors for polymers Inorganic acids, binary azeotropes with Inorganic compounds: nomenclature of physical constants of physical properties of proton-transfer reactions of solubilities in water at various temperatures solubility rules for synonyms and mineral names thermodynamic properties of vapor pressures of Inorganic ions: infrared frequencies of limiting equivalent conductances Integrals Intercept of best-fit line, errors in International temperature scale, fixed points in International Union of Pure and Applied Chemistry, nomenclature: of inorganic compounds of organic compounds Interplanar spacings for Kα1 radiation, of α-quartz for Kα1 radiation, of silicon Interplanar spacings, standards for Iodate, formation constants with Iodide, formation constants with

Links 10.22 2.87 2.87 11.130 2.118 8.116 11.96 8.122 11.109 4.47 11.51 7.29 9.2 7.41 7.68 7.67 10.6 5.58 3.1 3.12 5.130 8.18 5.9 11.105 3.62 6.81 5.31 7.64 8.157 2.105 2.35 11.138

3.1 1.1 7.13 7.14 7.14 7.13 8.85 8.85

25 Index Terms Iodine: bond dissociation energies gravimetric factors overpotential of titrimetric factors Iodine titrant, volumetric factors for Iodine value: of fats and oils of waxes lon-exchange lon-exchange resins, guide to Ion product constant of water at various temperatures Ionic character of a bond Ionic conductances, limiting equivalent Ionic crystal lattices Ionic equivalent conductivity, defined Ionic mobility, defined Ionic radii in aqueous solutions of elements Ionic strength Ionization energy: of elements of molecular species of radical species Ionization of metals in a plasma Ionized emission lines of elements lonomer polymers Ions: activity coefficients in water enthalpy of formation limiting equivalent conductances Indium, bond dissociation energies Iron: bond dissociation energies gravimetric factors Iron vs. copper-nickel alloy thermocouple Isobutyric acid, binary azeotropes with Isopolyanions, inorganic, nomenclature of Isotactic arrangement Isotopic abundances: naturally occurring elements of selected elements Isotopically labeled compounds, nomenclature of ITS-90, fixed points in IUPAC (see International Union of Pure and Applied Chemistry) Izod impact strength of polymers Josephson frequency-voltage ratio Joule-Thompson coefficient for real gases

Links 4.47 11.51 8.140 11.78 11.78 10.69 10.72 11.37 11.32 8.6 4.29 8.157 4.57 8.169 8.169 4.34 8.4 4.29 8.2

8.5

4.6 4.8 4.8 7.40 7.34 10.17 8.3 6.2 8.157 4.47 4.47 11.51 11.139 11.140 11.144 5.65 3.7 10.3 4.81 7.123 7.124 3.4 11.137 11.138

10.22 2.5 5.172

26 Index Terms Kα1 lines, mass absorption coefficients for Kelvin, definition of Kelvin scale, conversion to other thermometer scales Ketenes, nomenclature of Ketones: binary azeotropes with infrared frequencies of nomenclature of Raman frequencies of Kilogram, definition of Kinematic viscosity Kinetics, symbols, SI units, and definitions for Kovats retention indices Krypton: bond dissociation energies solubility in water at various temperatures Laboratory solutions Lactarns, nomenclature of Lactic acid, formation constants with Lactides, nomenclature of Lactims, nomenclature of Lactometers Lactones: infrared frequencies of nomenclature of Ladder polymer, defined Lanthanum, bond dissociation energies Laser lines of argon-ion plasma Latitude-gravity corrections for barometry Lattice types of crystal structures Laws of photometry Lead: bond dissociation energies gravimetric factors Least squares or best-fit line Length Level of significance, in statistics Ligand names, abbreviations for Ligands: abbreviations for names attachment points of inorganic, nomenclature of Limiting equivalent ionic conductances Linear free energy relationships Linear polymers, defined Linear thermal expansion of elements Liquids: electrical conductivity of pure thermal conductivities of

Links 7.16 2.3 2.66 1.32 5.61 7.51 1.32 7.78 2.3 5.138

5.74

2.14 11.26 4.47 5.8 11.106 1.34 8.96 1.34 1.34 2.67 7.50 1.34 10.3 4.47 7.89 2.75 4.57 7.38 4.47 11.52 2.133 2.3 2.124 3.11 3.11 3.10 3.10 8.157 9.2 10.3 4.2 8.161 5.150

3.4

27 Index Terms Lithium: bond dissociation energies gravimetric factors Logarithmic series Logarithms Lorentz and Lorenz equation Low-density polyethylene, properties of Lubricants for polymers Luminous intensity Lutetium, bond dissociation energies Magnesium: bond dissociation energies gravimetric factors Magnesium chloride brines, freezing point of Magnetic flux quantum Magnetic moment: of elements of protons in water Magnetism, symbols, SI units, and definitions for Manganese: bond dissociation energies gravimetric factors Mantissa of a common logarithm Masking agents (table) Mass Mass absorption coefficients for Kα1 and W Lα1 lines Mass differences, exact Mass spectra, correlation with molecular structure Mathematical symbols and abbreviations Maximum allowable exposure limits for gases and vapors Maximum recommended service temperature of polymers McReynold's constants in gas chromatography Mean free path of gases Mean ionic activity coefficient Mean of set of numbers Measurements, distribution of Measures of dispersion of data Mechanical properties of polymers Mechanics, symbols, SI units, and definitions for Median of set of numbers Medium-density polyethylene, properties of Melamine formaldehyde polymer: description of properties of

Links 4.47 11.53 2.115 2.102 5.135 10.44 10.6 2.3 4.48

4.48 11.53 5.86 2.5 7.89 2.5 2.10 4.48 11.54 2.102 11.92 11.98 2.3 7.15 7.124 7.123 2.23 11.121 10.22 11.21 5.171 8.2 2.111 2.111 2.114 10.22 2.15 2.118

10.44 10.13 10.32

28 Index Terms

Links

Melmine phenolic, woodflour-cellulose, filled plastic properties of 10.34 M elting, enthalpy of 6.4 of inorganic compounds 6.112 of organic compounds 6.51 Melting point: of inorganic compounds 3.14 molecular lowering of 11.4 of organic compounds 1.76 of waxes 10.72 Melting temperature of polymers 10.22 Membrane filters 11.70 Mercury: bond dissociation energies 4.48 density at various temperatures 5.87 gravimetric factors 11.55 vapor pressure of 5.24 Metal-carbon bond lengths 4.38 Metal complexes, formation constants of 8.83 Metal salts of organic acids, solubilities in water at various temperatures 5.9 Metastable peaks, use in mass spectrometry 7.125 Meter, definition of 2.3 Methacrylate monomers 10.10 Methane, solubility in water at various temperatures 5.6 Methanol: binary azeotropes with 5.66 pKa values in 8.81 ternary azeotropes with 5.77 Methanol-water mixtures, freezing point of 5.83 Methine protons: chemical shift of 7.92 estimation of chemical shift for 7.94 3-Methyl-l-butanol: binary azeotropes with 5.70 ternary azeotropes with 5.78 2-Methyl-l-propanol, ternary azeotropes with 5.78 2-Methyl-2-propanol: binary azeotropes with 5.69 ternary azeotropes with 5.78 Methyl protons, chemical shift of 7.92 Methylene protons: chemical shift of 7.92 estimation of chemical shift for 7.94 Micropipets, tolerances for 11.103 Millimeters mercury, conversion to other pressure units 2.87 Millimeters water, conversion to other pressure units 2.87 Mineral names of inorganic compounds 3.61 Minimum radius ratio of hybrid bonds 4.56 Mixed acid-base indicators 8.118

5.82

29 Index Terms Mode for set of numbers Moist air: density of refractive index of Molal values from molar values Molar absorptivity, defined Molar equivalent of 1 liter of gas at various pressures and temperatures Molar refraction Molar values, conversion to molal Molar volume, ideal gas Mole, definition of Molecular formula: of inorganic compounds of organic compounds Molecular geometry Molecular lowering of the melting point Molecular structure, determination from mass spectra Molecular weight: determined by lowering of melting point determined by molecular elevation of boiling point Molecules: electron affinities of ionization energy of symbols, SI units and definitions Molybdenum: bond dissociation energies gravimetric factors Monoclinic crystal lattices Monocyclic aliphatic and aromatic hydrocarbons, nomenclature of Multiplicative prefixes in inorganic nomenclature Multiplying affixes Must hydrometer Naperian base (e) Naphthalenes, Raman frequencies of Natural abundance: of elements of nuclides Natural rubber: description of properties of synthetic Naturally occurring isotopes, relative abundance of NBR rubber NBS (see NIST, National Institute for Science and Technology) Near infrared region, absorption frequencies in Neodymium, bond dissociation energies

Links 2.118 5.88 5.135 2.88 7.39 2.88 5.135 2.88 2.5 2.3 3.2 1.76 4.56 11.4

3.14

7.123 11.4 11.13 4.25 4.8 2.6 4.48 11.55 4.57

4.58

1.5 3.10 1.21 2.68 2.117 7.82 7.89 4.59 10.58 10.63 10.60 4.81 10.59

7.64 4.48

7.89

30 Index Terms Neon-neon bond dissociation energy Neon, solubility in water at various temperatures Neoprene Neptunium-oxygen bond dissociation energy Neutral inorganic radicals, nomenclature of Neutron rest mass New York Board of Health lactometer Newtons per square meter, conversion to other pressure units Nickel: bond dissociation energies gravimetric factors Nickel-chromium: vs. copper-nickel alloys thermocouple vs. nickel-aluminum alloys thermocouple Niobium, gravimetric factors Niobium-oxygen bond dissociation energy NIST pH buffer solution Nitrate, formation constants with Nitric oxide, solubility in water at various temperarores Nitrile polymers: description of properties of Nitrile rubber Nitriles: binary azeotropes with nomenclature of Nitrilotriactic acid, formation constants with Nitro compounds: infrared frequencies of Raman frequencies of Nitrogen: bond dissociation energies gas permeability of polymers and rubbers gravimetric factors solubility in water at various temperatures Nitrogen-carbon: bond lengths spin coupling constants Nitrogen-15: chemical shifts chemical shifts for standards chemical shifts in monosubstituted pyridine Nitrogen-14 NMR data (see Nitrogen-15) Nitrogen-fluorine spin coupling constants Nitrogen-hydrogen bonds: infrared frequencies Raman frequencies of Nitrogen-hydrogen spin coupling constants Nitrogen-nitrogen double bonds, Raman frequencies of Nitrogen-other elements bond lengths

Links 4.48 5.8 10.60 4.48 3.5 2.4 2.67 2.87 4.48 11.55 11.139 11.140 11.143 11.139 11.140 11.145 11.56 4.48 8.105 8.106 8.86 5.6 10.13 10.34 10.59 5.62 1.35 8.96 7.55 7.81 4.48 10.66 11.56 5.6 4.37 7.116 7.112 7.115 7.115 7.116 7.46 7.75 7.115 7.81 4.39

31 Index Terms Nitrogen-oxygen double bonds, Raman frequencies of 1-Nitroso-2-naphthol, formation constants with Nitrous oxide, solubility in water at various temperatures NMR frequency of elements for 1-kG field NMR sensitivity at constant field of elements NMR spectroscopy Nomenclature: of inorganic compounds of organic compounds Nonaqueous solvents: pKa values in potential ranges in Nonfunctional organic compounds, nomenclature of Normal distribution curve in statistics Novolac resin, properties of Nuclear magnetic resonance Nuclear magneton Nuclear properties of elements Nuclear reactions, symbols for Nuclear spin of elements Nuclides: capture cross section, thermal natural abundance of properties of radiation emitted Numbering of organic compounds Numerical prefixes Nylon II polymers: description of properties of Nylon 6 polymers: description of properties of Nylon 6/9 polymers: description of properties of Nylon 6/6-nylon 6 copolymer, properties of Nylon 6/6 polymers: description of properties of Nylon 6/12 polymers: description of properties of Nylon 12 polymer: description of properties of Octahedral covalent radii of elements Oils, properties of Oleometer

Links 7.85 8.97 5.8 7.89 7.89 7.92 3.1 1.1 8.81 8.80 1.1 2.119 10.11 10.30 7.89 2.5 4.58 7.89 2.8 7.89 4.59 4.59 4.58 4.59 1.20 2.25 10.14 10.38 10.14 10.36 10.14 10.38 10.36 10.14 10.36 10.14 10.38 10.14 10.38 4.36 10.69 2.68

7.89

32 Index Terms

Links

One-tailed test, in statistics Optical rotation Orbitals, hybridized Ordinates and areas of normal distribution curve Organic acids: binary azeotropes with salts of, solubilities at various temperatures Organic compounds: dielectric constants dipole moments empirical formula index of half-wave potentials physical properties of proton-transfer reactions of surface tensions thermodynamic properties of vapor pressures of viscosity of Organic ions, limiting equivalent conductances Organic radicals, names and formulas of Organic solvents arranged by boiling points Organosulfur halides, nomenclature of Orientation, spatial, of common hybrid bonds Orthorhomic crystal lattices Osmium-oxygen bond dissociation energy Ostwald dilution law Overpotentials of electrode reactions Oxalate, formation constants with Oxidation numbers, in inorganic formulas Oxidation-reduction indicators Oxidation-reduction titrants Oxidation-reduction titrations, equations for Oximes, infrared frequencies of Oxygen: bond dissociation energies gas permeability of polymers and rubbers overpotential solubility in water at various temperatures Oxygen-carbon bond lengths Oxygen-hydrogen bonds, infrared frequencies Oxygen-other elements bond lengths Ozone, solubility in water at various temperatures

2.125 1.46 4.56

Palladium, gravimetric factors -oxygen bond dissociation energy Parabola, properties of Parallelogram, area of Particles, symbols for Partition ratio Pascals, conversion to other pressure units Path length, of cuvettes PCTA copolyester

11.57 4.49 2.111 2.109 2.8 11.28 2.87 7.40 10.16

2.119 5.58 5.9

5.62

5.105 5.105 1.58 8.146 1.76 5.90 8.24 5.90 6.5 6.51 5.39 5.90 8.157 1.51 11.10 1.38 4.56 4.57 4.58 4.49 8.169 8.140 8.97 3.4 8.122 11.83 11.82 11.84 7.54 4.49 10.66 8.140 5.6 4.37 7.44 4.29 5.8

33 Index Terms Peak asymmetry factor Percent absorption to absorbance, table Percent humidity: of calcium chloride solutions of sodium hydroxide solutions of sulfuric acid solutions at various temperatures for various solutions Perfluoroalkoxy polymer: description of properties of Permanganate, volumetric factors for Permeability of vacuum Peroxides: infrared frequencies of nomenclature of pH buffer solutions, standard reference pH measurement: of blood and biological materials electrometric in 50 weight percent methanol-water pH range: of acid-base indicators of fluorescent indicators pH values: for buffer solutions in alcohol-water solvents of solutions, calculation of approximate 1,10-Phenanthroline, formation constants with Phenol, binary azeotropes with Phenol-formaldehyde resin Phenolic polymers: description of properties of Phenols: nomenclature of retained trivial names of Phosphate reference pH buffer solutions at various temperatures Phosphate-succinate reference pH buffer solution Phosphorus: bond dissociation energies gravimetric factors other elements bond lengths Phosphorus compounds: infrared frequencies of nomenclature of Phosphorus-31: chemical shifts spin coupling constants Photometry, laws of Phthalate reference pH buffer solution at various temperatures Phthalic acid, formation constants with

Links 11.28 11.29 2.96 11.7 11.7 11.7 11.6 10.12 10.30 11.86 2.5 7.58 1.35 8.104 8.106 8.115 8.109 8.116 8.120 8.109 8.17 9.98 5.71 10.14 10.14 10.34 1.24 1.25 8.105 8.108 4.49 11.57 4.40 7.60 1.36 7.119 7.122 7.38 8.105 9.99

8.23

34 Index Terms Physical chemistry equations for gases Physical constants, fundamental Physical properties: of inorganic compounds of organic compounds of polymers Physical symbols and definitions pi (π), value of Piperidine, formation constants with Pipet capacity tolerances pKa values at various temperatures pKa values: of acid-base indicators of inorganic materials in nonaqueous solvents of organic materials pKoa values: for Hammett equation for Taft equation Planck constant Planck radiation law Plane angle Plant fats and oils, properties of Plastic families (table) Plasticizers for polymers Plastics, commercial: formulas and key properties of properties of commercial Plate height Plate number Platinum: bond dissociation energies gravimetric factors Platinum-10% rhodium alloy vs. platinum thermocouple Platinum-13% rhodium alloy vs. platinum thermocouple Platinum-30% rhodium vs. platinum-6% rhodium alloys Polyacrylate rubbers Poly(acrylic acid) and poly(methacrylic acid) copolymer Poly(acrylonitrile) polymers Polyallomer polyolefin polymer, properties of Polyamide polymers: description of properties of Poly(amide-imide) polymers: description of properties of Poly(aryl ether) polymer, properties of Polyatomic inorganic anions, nomenclature of Polybutadiene rubber

Links 5.169 2.3 3.12 1.76 10.22 2.6 2.117 8.99 11.103 8.73 8.116 8.18 8.81 8.24

8.73

9.7 9.8 2.5 11.138 2.3 10.70 10.6 10.7 10.8 10.22 11.28 11.28 4.44 11.58 11.139 11.140 11.148 11.139 11.140 11.147 11.139 10.59 10.9 10.10 10.46 10.14 10.36 10.15 10.38 10.40 3.7 10.59

35 Index Terms Polybutylene polymers Polybutylene extrusion polymer, properties of Poly(butylene terephthalate) polymers: description of properties of Polycarbonate polymer: description of properties of Polycarbonate-acrylonitrile-butadiene-styrene alloy Polychloroprene rubber Poly(chlorotrifluoroethylene) polymer: description of properties of Polycyclic hydrocarbons, fused, nomenclature of Poly(1,4-cyclohexanedimethylene terephthalic acid) polymer Polyester polymers Polyester thermoplastic elastomers, properties of Polyesters Poly(ether sulfone) polymer, properties of Polyethylene polymers: description of properties of Poly(ethylene terephthalate) polymers: description of properties of Polygon, area and properties of Polyhedra, area of surface and volume Polyimide polymers: description of properties of Polyisobutylene rubber Polyisoprene rubber Polymers: additives to gas permeability of properties of commercial resistance to chemicals structural differences vapor permeability constants for Poly(methyl acrylate) Poly(methyl methacrylate) polymer: description of properties of Poly(methylpentene) polymer: description of properties of Polyolefin polymers in elastomers properties of

Links 10.17 10.46 10.15 10.40 10.15 10.40 10.26 10.60 10.12 10.30 1.6 10.16 10.15 10.20 10.54 10.15 10.20 10.52 10.16 10.44 10.15 10.40 2.110 2.112 10.16 10.42 10.60 10.60 10.2 10.4 10.66 10.22 10.64 10.3 10.69 10.9 10.9 10.24 10.16 10.44 10.16 10.20 10.44

36 Index Terms Polyolefin thermoplastic elastomers, properties of Poly(phenyl sulfone) polymer, properties of Poly(phenylene sulfide) polymer: description of properties of Polypropylene polymers: description of properties of Polysiloxanes Polystyrene polymers: description of properties of Polysulfide rubbers Polysulfone polymers: description of properties of Poly(tetrafluoroethylene) polymer: description of properties of Poly(vinyl acetate) polymer Poly(vinyl alcohol) polymer Poly(vinyl butyral) polymer: description of properties of Poly(vinyl chloride): description of properties of Poly(vinyl chloride) and poly(vinyl acetate) polymers, properties of Poly(vinyl fluoride) polymer Poly(vinyl formal) polymer, properties of Poly(vinylidene chloride) polymer: description of properties of Poly(vinylidene fluoride) polymer: description of properties of Polyurethane polymers: description of properties of Pore sizes: of fritted glassware of membrane filters Potassium: bond dissociation energies gravimetric factors Potassium dichromate, volumetric factors for Potassium permanganate, volumetric factors for Potentials of elements and their compounds Pounds per square inch, conversion to other units Praseodymium, bond dissociation energies

Links 10.54 10.52 10.17 10.46 10.17 10.46 10.19 10.19 10.48 10.61 10.20 10.52 10.12 10.30 10.21 10.21 10.21 10.56 10.20 10.56 10.54 10.13 10.56 10.21 10.58 10.56 10.13 10.32 10.18 10.48 11.60 11.60 4.32 11.58 11.79 11.80 8.124 2.87 4.49

37 Index Terms Precipitates, heating temperatures, composition of weighing forms, and gravimetric factors Precipitation titrations indicators for standard solutions for Prefixes: numerical (multiplying) SI use in inorganic formulas Pressure, altitude variation of Pressure conversion chart Pressure, critical Prestone-water mixtures, freezing point of Primary standards: for acid-base titrations for precipitation titrations for redox titrations Prismoid, volume of Probability curve Promethium, bond dissociation energies 1-Propanol, binary azeotropes with 1-Propanol, ternary azeotropic mixtures 2-Propanol, binary azeotropes with 2-Propanol, ternary azeotropic mixtures Properties of plastic materials Propionic acid: binary azeotropes with ternary azeotropic mixtures Propylene glycol-water mixtures, freezing point of Propylene-1,2-diamine, formation constants with Protective colloids Proton chemical shifts: attached to a double bond in monosubstituted benzene of reference compounds Proton magnetic moment Proton magnetogyric ratio Proton resonance frequency per field in water Proton rest mass Proton spin coupling constants Proton-transfer reactions of inorganic materials in nonaqueous solvents of organic materials at various temperatures Protonated inorganic anions, nomenclature of Protons attached to double bond, estimation of chemical shift of Psi, conversion to other pressure units Pyknometer, determinations with

Links

11.72 11.89 11.94 11.95 2.25 2.25 3.2 2.78 2.87 6.143 5.84 11.74 11.94 11.82 2.112 2.119 4.50 5.67 5.77 5.68 5.77 10.8 5.64 5.82 5.85 8.99 11.95 7.92 7.95 7.95 7.98 2.5 2.5 2.5 2.5 7.97 8.17 8.18 8.81 8.24 8.73 3.6 7.95 2.87 5.89

8.73

38 Index Terms Pyridine: binary azeotropes with carbon-13 chemical shifts in substituted fonnation constants with nitrogen-l5 chemical shifts in monosubstituted Pyridine-2,6-dicarboxylic acid, formation constants with 1-(2-Pyridylazo)-2-naphthol, formation constants with 4-(2-Pyridylazo)resorcinol, formation constants with Pyrocatechol-3,5-disulfonate, formation constants with Pyrophosphate, formation constants with Quadratic mean of set of numbers Quadrupole moment of elements Quantum of circulation Quantum-charge ratio Quantum yield values, fluorescence Quartz, int erplanar spacings with Kα 1 radiation Quevenne lactometer δ-Quinolinol, formation constants with Radian, definition of Radiation buffer Radiation: electromagnetic, symbols, SI units, and definitions for emitted by radionuclides Radical species, ionization energy of Radicals: electron affinities of from ring systems, nomenclature of Radicofunctional nomenclature Radioactivity from nuclides Radium-chlorine bond dissociation energy Radius ratio, minimum Radon, solubility in water at various temperatures Raman frequencies: of aromatic compounds of carbonyl bands of cumulated double bonds of double bonds of ethers of halogen compounds of heterocyclic rings of single bonds to hydrogen and carbon of sulfur compounds of triple bonds Raman spectroscopy Random errors

Links 5.75 7.115 8.99 7.115 8.99 8.100 8.100 8.99 8.86 2.119 7.89 2.5 2.5 7.28 7.14 2.67 8.101 2.3 7.41

2.12 4.59 4.8 4.27 1.10 1.22 4.59 4.50 4.56 5.8 7.82 7.78 7.76 7.79 7.85 7.86 7.87 7.71 7.84 7.76 7.71 2.118

39 Index Terms Rankine scale, conversion of Ratio, electron-to-proton magnetic moments Rayon Reaction parameters in Harnmett equation Reactive and incompatible chemicals Reagents, preparation of Reaumur scale, conversion of Rectangle, area of Reduced plate height Reduced velocity Redwood seconds at several temperatures Reference compounds in NMR: proton chemical shifts of for nitrogen-15 chemical shifts Reference electrodes Refractions, atomic and group (table) molar Refractive index: of chromatographic solvents discussion of of fats and oils of moist air of organic compounds of solvents of water at various temperatures of waxes Refrigerated storage, chemical recommended for Relative abundance of naturally occurring isotopes Relative humidity: from dew point readings from wet and dry bulb thermometer readings Relative retention Replacement nomenclature Residual protons (NMR) in incompletely deuterated solvents Resistance, chemical: of polymers of rubbers Resistivity: defined electrical, of elements (see also Conductivity) Resolution Resonance effect of a substituent Retention behavior of solutes in chromatography Retention time (or volume) Reversing a series Reynolds number

Links 2.66 2.5 10.11 9.2 11.130 11.109 2.66 2.109 11.31 11.31 2.82

9.7

7.98 7.115 8.113 5.135 5.135 11.16 5.135 10.69 5.135 1.76 11.18 5.134 10.72 11.136 4.81 11.9 11.8 11.28 1.22 7.98 10.64 10.65 8.168 4.2 11.28 11.29 9.2 11.27 11.27 2.116 5.138

40 Index Terms Rho values: for Hammett equation in nucleophilic substitutions for special reaction centers Rhodium: bond dissociation energies gravimetric factors Rhombohedral crystal lattice Ring assemblies of hydrocarbons, nomenclature of Ring systems, radicals from, nomenclature of Rockwell hardness of polymers Root mean square RT/nF values at several temperatures Rubbers: gas permeability of properties of natural and synthetic resistance to chemicals Rubidium: bond dissociation energies gravimetric factors Ruthenium, bond dissociation energies Rydberg constant Saccharometers Saha equation Salicylaldoxime, formation constants with Salicylic acid, formation constants with Salinometer Salts: of inorganic acids, nomenclature of of organic acids, nomenclature of Samarium, bond dissociation energies Sample decomposition, fluxes for Sample variance SAN copolymers: description of properties of Saponification value: of fats and oils of waxes Saturated air, mass of water vapor in, at various temperatures Saturated heterocyclic ring systems, proton NMR signal Saybolt universal viscosity at several temperatures Scandium, bond dissociation energies Screens, see sieves Sea level, reduction of barometer readings to Second, definition of Second radiation constant

Links 9.7 9.8 9.8 4.50 11.60 4.57 1.10 1.10 10.22 2.119 8.115 10.58 10.66 10.63 10.64 4.50 11.60 4.51 2.5 2.68 7.41 8.101 8.101 2.68 3.10 1.36 4.50 11.61 2.118 10.20 10.52 10.69 10.72 5.156 7.93 2.82 4.50 2.79 2.3 2.5

4.58

41 Index Terms Selection rules: for parent heterocyclic system for principal alicyclic chain for principal ring system Selectivity coefficients for ion-exchange resins Selenium: bond dissociation energies gravimetric factors Selellium-carboll bond lengths Self-ignitioll temperatures of combustible mixture in air Sensitivity of elements at constant field (NMR) Separation methods Sequence rules, geometrical isomers and chiral compounds Service temperature: of commercial plastics of rubbers of commercial plastics Shore hardness: of polymers of natural and synthetic rubbers SI prefixes SI units: base definition of derived supplementary Sieve openings Sieve sizes, U.S. standard Silica, solvent strength parameters Silicon: bond dissociation energies gravimetric factors interplanar spacings with Kα1 , radiation Silicon compounds: infrared frequencies of nomenclature of Silicon-carboll bond lengths Silicone polymers, properties of Silicone rubbers Silicones Silicon-other elements bond lengths Silicon-29 chemical shifts Silver: bond dissociation energies gravimetric factors Silver nitrate, volumetric factors for Silver/silver bromide reference electrode, EMF as function of temperature Silver/silver chloride reference electrode, EMF as function of temperature Silver/silver iodide reference electrode, EMF as function of temperature

Links 1.15 1.18 1.18 11.37 4.50 11.60 4.38 5.139 7.89 11.16 1.44 10.23 10.63 10.22 10.63 2.24 2.3 2.3 2.4 2.3 11.137 11.137 11.16 4.50 11.61 7.14 7.61 1.37 4.38 10.48 10.61 10.18 4.40 7.119 4.50 11.61 11.81 8.113 8.113 8.113

42 Index Terms Single-bond radii, of elements Single bonds between hydrogen and carbon: infrared frequencies of Raman frequencies of Single bonds between hydrogen and oxygen, infrared frequencies Single bonds between hydrogen and nitrogen Single-bond radii, of elements Slope of best-fit line, errors in Sodium: bond dissociation energies gravimetric factors Sodium chloride brines, freezing point of Sodium hydroxide solutions, percent humidity of Sodium thiosulfate solution, volumetric factors for Solid angle Solid state, symbols, SI units, and definitions for Solidification point, of fats and oils Solids, thermal conductivities Solid state, symbols, SI units, and definitions for Solubility: of gases in water at various temperatures of inorganic compounds in water at various temperatures of organic compounds Solubility products: at various temperatures Solubility rules for inorganic compounds Solute band profile Solutes, chromatographic behavior of Solutions for analytical use, preparation of Solvent strength parameter Solvents: acid-base, properties of arranged by boiling points of chromatographic interest correction for in ultraviolet-visible region having the same refractive index and same density infrared transmission characteristics positions of residual protons (NMR) in incompletely deuterated ultraviolet cutoffs of Soxhlet lactometer Space, symbols, SI units, and definitions for Spatial orientation of common hybrid bonds Specialist nomenclature for heterocyclic systems

Links 4.35 7.41 7.71 7.44 7.46 4.35 2.135 4.51 11.61 5.86 11.7 11.82 2.3 2.16 10.69 5.154 2.16 5.3 3.14 5.9 1.76 8.6 8.73 11.105 11.29 11.27 11.109 11.16 8.90 11.10 11.16 7.23 11.18 7.68 7.98 7.20 2.67 2.17 4.56 1.11

43 Index Terms Specific gravity: conversion to density corrections for buoyant effect of air of fats and oils of polymers of rubbers of waxes Specific heat: of any phase of polymers (see also Heat capacities) Specific refraction Specific resistance Specific rotation Spectrophotometry, laws of Spectroscopic relationships Spectroscopy, symbols, SI units, and definitions for Speed of light in vacuum Sphere, area and volume of Spin coupling constants: carbon-carbon carbon-fluorine of carbon-hydrogen of carbon with nuclei other than hydrogen fluorine-fluorine nitrogen-fluorine nitrogen-hydrogen of phosphorus of protons Spin, nuclear, of elements Sprayometer Stability constants (see Formation constants) Standard acceleration of free fall Standard atmosphere Standard deviation: of chromatographic band in statistics Standard enthalpies for compounds Standardized variable Standard letter symbols Standard stock solutions for elements Standards: for acid-base titrations for fluorescence for precipitation titrations for redox titrations States of aggregation, abbreviations for Stationary phases in gas chromatography Statistical tables Stefan's law Stefan-Boltzmann constant Steradian, definition of Stereochemistry

Links 5.87 2.66 5.89 10.69 10.22 10.63 10.72 6.4 10.23 5.135 8.168 1.47 7.39 7.38 2.16 2.5 2.112 7.108 7.109 7.107 7.110 7.118 7.116 7.115 7.122 7.97 7.89 2.68 2.5 2.5 11.29 2.120 6.2 2.120 2.26 11.107 11.74 7.28 11.94 11.82 2.7 11.21 2.117 7.39 2.5 2.3 1.39

44 Index Terms Stereoisomers Stoichiometric proportions, in inorganic nomenclature Straight-chain alkanes, names of Strontium: bond dissociation energies gravimetric factors Structural formulas (see Formulas) Student t values (table) Student's distribution Styrene-acrylonitrile copolymers: description of properties of Styrene-butadiene copolymer, properties of Styrene-butadiene rubber Styrene-butadiene-styrene block copolymers Styrene-maleic acid copolymer, properties of Styrenic polymers: description of properties of Sublimation, enthalpy of: of inorganic compounds of organic compounds Sublimation, entropy of Substitution pattern of benzene ring: infrared frequencies Raman frequencies Substitutive nomenclature Succinic acid, formation constants with Sucrose-water solutions, density and viscosity of Suffixes for specialist nomenclature of Heterocyclic systems Sulfate, formation constants with Sulfite, formation constants with Sulfone polymers: description of properties of Sulfones, nomenclature of Sulfonium compounds, nomenclature of 5-Sulfosalicylic acid, formation constants with Sulfoxides, nomenclature of Sulfur acids, nomenclature of Sulfur: bond dissociation energies -carbon bond lengths gravimetric factors -other elements bond lengths Sulfur compounds: infrared frequencies of nomenclature of Raman frequencies of Sulfur dioxide, solubility in water at various temperatures

Links 1.39 3.3 1.2 4.51 11.63 2.124 2.123 10.19 10.52 10.52 10.61 10.20 10.42 10.19 10.48 6.3 6.124 6.51 6.4 7.57 7.82 1.17 8.102 5.138 1.12 8.86 8.87 10.20 10.52 1.38 1.38 8.102 1.38 1.38 4.51 4.38 11.64 4.40 7.59 1.37 7.84 5.6

45 Index Terms Sulfuric acid solutions: percent humidity of specific vapor pressures of Sultams, nomenclature of Sultones, nomenclature of Supercritical fluids, table Suppression of ionization in a plasma Surface areas and volumes Surface chemistry, symbols, SI units, and definitions for Surface tension: discussion of of inorganic compounds of organic compounds of water at various temperatures Symbols: of elements mathematical physical and chemical standard letter Symmetry in crystal structures Syndiotactic arrangement Synonyms of inorganic compounds Synthetic rubbers: defined natural properties of Systematic errors t, values of t test Tacticity, defined Taft sigma values Taft substituent constants Tantalum: bond dissociation energies gravimetric factors Tartaric acid, formation constants with Tartrate reference pH buffer solution at various temperatures Tellurium: bond dissociation energies gravimetric factors Temperature correction, for barometric readings Temperature conversion between Celsius and Fahrenheit scales critical measurement of Tensile modulus of polymers Tensile yield strength: at break of polymers of natural and synthetic rubbers

Links 11.7 11.7 1.39 1.39 11.26 7.41 2.109 2.10 5.136 5.130 5.90 5.134 4.2 2.23 2.6 2.26 4.58 10.3 3.61 10.3 10.60 10.63 2.118 2.124 2.123 10.3 9.2 9.2 4.51 11.64 8.102 8.105 4.51 11.64 2.72 2.3 2.54 6.141 11.138 10.22 10.22 10.63

46 Index Terms Tension, aqueous (see Vapor pressure) Terbium, bond dissociation energies Ternary azeotropic mixtures containing water and alcohols Tests of significance, in statistics Tetragonal crystal lattices Tetraoxalate reference pH buffer solution at various temperatures Thallium: bond dissociation energies gravimetric factors Theoretical plates Thermal conductivity: of elements of gases at various temperatures of liquids at various temperatures of polymers of solids Thermal expansion: cubical coefficients of linear, coefficient of, elements Thermal neutron absorption cross section of nuclides Thermal properties of polymers Thermocouples Type B Type E Type I Type K Type N Type R Type S Type T Thermodynamtic properties Thermodynamtics, symbols, SI units, and definitions for Thermoelastic elastomers Thermometer scales, conversion between Thermometers, correction for emergent stem Thermometry Thermoplastic elastomers: defined properties of Thermoplastic polyester polymers Thermoplastic polyurethane elastomer, properties of Thermosetting alkyd polyesters, properties of Thermosetting polymers, defined Thiocyanate, formation constants with Thioesters and thioacids, infrared frequencies of Thioglycolic acid, formation constants with Thiophene, binary azeotropes with

Links 4.51 5.77 5.77 2.126 4.53

4.57

8.105 4.51 11.65 11.28 5.148 4.2 5.148 5.151 10.23 5.154 11.105 4.2 4.59 10.22 11.138 11.139 11.139 11.139 11.139 11.139 11.139 11.139 11.139 6.1

11.140 11.140 11.140 11.140 11.140 11.140 11.140

2.19 10.20 2.59 11.150 11.137 10.2 10.20 10.54 10.40 10.48 10.42 10.2 8.87 7.53 8.103 5.76

11.143 11.144 11.145 11.146 11.147 11.148 11.149

47 Index Terms Thiosulfate: formation constants with volumetric factors for Thiourea, formation constants with Thomson cross section Thorium: bond dissociation energies gravimetric factors Thoron, formation constant with Threshold limit value (TLV) for gases and vapors Thullium, bond dissociation energies Time: of analysis in chromatography defined symbols, SI units, and definitions for Tin: bond dissociation energies gravimetric factors Tiron, formation constants with Titanium: bond dissociation energies gravimetric factors Titrimetric factors: acids bases iodine potassium dichromate potassium permanganate silver nitrate sodium thiosulfate Titrimetric solutions, standard: for acid-base titrations for elements for precipitation titrations for redox titrations Tolerances: for analytical weights for burets for pipets for volumetric flasks Torsional asymmetry Torus, area and volume of Tralle hydrometer Transference numbers Transmittance: to absorbance (table) defined Transport properties, symbols, SI units, and definitions for Trapezoid, area of Triangle, area of Triclinic crystal lattice Triethanolamine, formation constants with

Links 8.87 11.88 8.103 2.5 4.51 11.65 8.103 11.121 4.51 11.31 2.3 2.17 4.51 11.65 8.91 4.52 11.65 11.76 11.77 11.78 11.79 11.80 11.81 11.82 11.84 11.107 11.94 11.82 11.71 11.103 11.103 11.102 1.47 2.113 2.68 8.169 2.98 7.39 2.21 2.109 2.109 4.57 8.103

48 Index Terms Triethylenetetrarnine, formation constants with 1,1,1-Trifluoro-3,2'-thenoylacetone, formation constants with Trigonometric functions: of an angle functions, series for Triple-bond radii, of elements Triple bonds: infrared frequencies of Raman frequencies of Triple points of various materials Trivial names of heterocyclic systems for use in fusion names Trouton's rule Tungsten: bond dissociation energies gravimetric factors Tungsten Lα1 line, mass absorption coefficients for Twaddell degrees: conversion to degrees Baume conversion to density Twaddell hydrometer Two-tailed test, in statistics Ultraviolet-visible spectroscopy Ultraviolet cutoff: of chromatographic solvents of spectrograde solvents Ultraviolet stabilizers for polymers Unit cells in crystal structures Unsaturated carbon-hydrogen bond, Raman frequencies Unsaturated polyester polymers Unsaturated cyclic ring systems, carbon-13 chemical shifts Unsaturated heterocyclic ring systems, proton chemical shifts in Uranium: bond dissociation energies gravimetric factors Urea formaldehyde resin description of properties of Ureas, infrared frequencies of Van der Waals' constants for gases Van der Waals' equation of state for gases Vanadium: bond dissociation energies gravimetric factors Vapor density, of gases

Links 8.103 8.104 2.113 2.116 4.35 7.47 7.76 5.168 1.13 6.3 4.52 11.66 7.16 2.85 2.85 2.68 2.125 7.19 11.16 7.20 10.7 4.59 7.73 10.16 7.101 7.94 4.52 11.66 10.21 10.58 10.54 7.53 5.157 5.157 5.170 4.52 11.66 5.171

49 Index Terms Vaporization: enthalpy of of inorganic compounds of organic compounds entropy of Vapor permeability constants for polymers Vapor-pressure equations Vapor pressure: of ammonia (liquid) of deuterium oxide of ice of inorganic compounds of mercury of water of organic compounds of solutions Variance in statistics Velocities of gas molecules Vinyl polymers: description of properties of Virial equation of state for gases Viscosity: of aqueous glycol solutions of chromatographic solvents conversions discussion of of inorganic compounds of organic compounds of sucrose solutions of water at various temperatures Voltammetric half-wave potentials: of inorganic materials of organic materials Volume: critical factors for simplified computation of of geometric objects Volume resistivity (dc) of polymers Volumetric analysis Volumetric factors Volumetric flasks, tolerances for Volumetric primary standards: acid-base titrations complexometric titrations precipitation titrations for redox titrations Vulcanization and curing Water: absorption by polymers binary azeotropes with boiling points of compressibility of

Links 6.3 6.124 6.51 6.4 10.69 5.29 5.27 5.30 5.26 5.31 5.24 5.28 5.39 11.6 2.114 5.171 10.20 10.54 5.170 5.138 11.16 2.82 5.137 5.130 5.90 5.138 5.134 8.141 8.146 6.143 11.104 2.109 10.22 11.74 11.76 11.102 11.74 11.91 11.94 11.82 10.7

10.22 5.58 5.57 5.150

50 Index Terms

Links

Water (Cont.) conductivity of pure, at various temperatures density at various temperatures dielectric constant, refractive index, surface tension, viscosity ion product constant of, at various temperatures ternary azeotropes with vapor pressure of Water vapor: gas permeability of polymers and rubbers mass of in saturated air Wavelength: defined maxima of acid-base indicators to wavenumber conversion, table and X-ray tube voltage relationship Wavenumber to wavelength conversion, table Waxes, properties of Weighings in air to weighings in vacuo, conversion of Weights, analytical, tolerances for Wet and dry bulb thermometer readings and relative humidity Wien displacement constant Wien displacement law Wijs solution for iodine number Wine and must hydrometer Woodward-Fieser rules Work functions of elements Writing formulas of inorganic compounds

11.8 2.5 7.38 11.121 2.68 7.19 4.80 3.1

Xenon: bond dissociation energies solubility in water at various temperatures X-ray absorption edges, wavelengths of X-ray absorption energies, critical X-ray emission energies X-ray emission spectra X-ray filters X-ray lines, mass absorption coefficients for X-ray methods X-ray spectroscopy, analyzing crystals for X-ray tube voltage and wavelength relationship Xylenol orange, formation constants with

4.52 5.8 7.5 7.8 7.10 7.3 7.14 7.16 7.2 7.15 7.39 8.104

Ytterbium, bond dissociation energies Yttrium, bond dissociation energies Zeeman splitting constant Zinc: bond dissociation energies gravimetric factors

8.168 5.87 5.134 8.6 5.79 5.28 10.66 5.156 7.38 8.116 2.101 7.39 2.101 10.72 2.83 11.71

4.52 4.52 2.4 4.52 11.66

51 Index Terms Zincon, formation constant with Zirconium: bond dissociation energies gravimetric factors z statistics

Links 8.104 4.53 11.67 2.120