Mass Spectral Correlations (1963 Edition)

ACS Library Executive Secretary's Office Publication Date: January 1, 1963 | doi: 10.1021/ba-1963-0040.fw001 Mass S...

Author: Fred McLafferty

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ACS Library

Executive

Secretary's

Office

Publication Date: January 1, 1963 | doi: 10.1021/ba-1963-0040.fw001

Mass Spectral Correlations

Fred W. McLafferty Eastern Research Laboratory Dow Chemical Co. Framingham, Mass.

ADVANCES IN CHEMISTRY SERIES 40

AMERICAN CHEMICAL SOCIETY WASHINGTON, D. C. 1963

In Mass Spectral Correlations; McLafferty, F.; Advances in Chemistry; American Chemical Society: Washington, DC, 1963.


Copyright © 1963 American Chemical Society A l l Rights Reserved

Library of Congress Catalog Card 63-17704 PRINTED IN THE UNITED STATES OF AMERICA

American Chemical Society Library 1155 16th St. N. W. In Mass Spectral Correlations; McLafferty, F.; Washington, D. C. 20036

Advances in Chemistry; American Chemical Society: Washington, DC, 1963.

Advances in Chemistry Series Robert F. Gould, Editor


Advisory Board Raymond F. Boyer John H. Fletcher Jack Halpern Wayne W. Hilty George W. Irving Walter C. Saeman Calvin L. Stevens Calvin A. Vanderwerf George A. Watt

AMERICAN CHEMICAL SOCIETY APPLIED PUBLICATIONS


Publication Date: January 1, 1963 | doi: 10.1021/ba-1963-0040.pr001

INTRODUCTION For a number of years, the mass spectrometer has been applied to the elucidation of problems in molecular structure. Correlations of mass spectra with structure have now been made for almost all of the common types of organic compounds (2, 8). Most of these correlations by necessity, emphasize the type of spectral pattern or decomposition paths to be expected for a particular type of molecular structure. However, in determining the structure of an unknown compound, the reverse situation is presented — i. e., the prominentions in the mass spectrum are known, from which one wishes to determine the most probable molecular structure or structures. When the reference mass spectrum of the unknown has been run previously, this can be located from the prominent peaks, using a number of filing systems previously described (5, 6, 9, 11, 14, 15). However, it obviously is highly desirable to have an identification system not dependent on the availability of the standard spectrum of the unknown. This similar problem in other fields of spectroscopy has led to charts or tables indicating the prominent functional groups or other structural features which are found at particular wave lengths. Perhaps such tabulations have been most widely used in infrared spectroscopy — e.g., "the Colthup chart" (4). Aprevious suggestion for such a system for mass spectrometry (9) has led to the accompanying tabulation of mass spectral correlations. GENERAL DESCRIPTION In designing this table, the purpose was to provide,where possible, the empirical and structural formulas of ions that might be found at a particular m/e in a mass spectrum, plus an indication of how each such ion might have arisen. A further purpose was to give an indication of the probability of each such classification of ions occurring. Thus, the table should indicate possible ion structures and precursor molecules for each of the prominent ions in the mass spectrum of an unknown compound, with afurther indication of the general probability of their occurrence. The mass spectral data used in this tabulation were available in a card file (9) containing a card for each of the 10 most prominent peaks in the 4000 referenced mass spectra. These cards were filed serially by nominal mass number with separation within each m/e by order of abundance in the particular mass spectrum. Thus, at m/e 123 in this file there appeared a card for each compound in which m/e 123 was one of the 10 most abundant ions in the mass spectrum. Cards for all compounds in which m/e 123 was the largest peak in the spectrum appeared l



2

A D V A N C E S I N CHEMISTRY SERIES

first, followed by those in which m/e 123 wasthe second largest, etc., through the 10th most abundant. To prepare the tabular correlation, each of the cards filed under a particular mass number was examined to ascertain the relationship of this peak in the spectrum to the structure of the compound. Where possible, the empirical and structural formulas and the mechanism of formation of the ion were assigned, plus the general structural type or functional group of the particular compound which gave rise to this ion. The number of cards under each such classification under the particular m/e were recordedfor each magnitude (second most abundant, etc.). Such data were accumulated for the three most abundant ions in all mass numbers filed (m/e 1-500), with less abundant ions being included for those mass numbers containing fewer cards in the three highest peaks. All 10 of the highest peaks in the spectra were included above m/e 218. Some ions were not included in the classifications because it was felt that they were not sufficiently representative of types of compound structures or functional groups. These are listed as the" P. I. D. ions," representing the "Parent" or molecular ions, ions due to isotopic species of smaller or artificial abundance — e.g., carbon -13 or deuterium — and doubly charged (or multiply charged) ions or other ions of fractional mass, as metastable ions. "Other unclassified" ions are those for which it was felt there was insufficient evidence of their structural significance for classification. PRESENTATION OF DATA m/e. The mass-to-charge ratio in the first column of the table is calculated from the assumed empiricalformula,using the atomic weight scale based on carbon = 12.000000. Almost all of the spectra used in this study, however, were run on instruments of insufficient resolving power to determine such fractional masses, so that it had to be assumed that eachpeak represented only one empirical formula. Thus, the significant figures shown are as calculated, not as determined. The correlations should still prove useful, however, where it is possible to determine the m/e of the unknown peak in question to millmass unit accuracies. As has been shown extensively by Beynon and coworkers (1,2), this will then make possible the assignment of the empirical formula within each of the unit mass classifications, and thus simplify the identification problem. There is a definite possibility that even the nominal mass number is in error, because of the very large number of spectra examined and the "uncertified" nature of these. This is especially true, naturally, at higher mass numbers, where resolution is decreased and mass markers become less reliable. However, many of these errors were eliminated because of the correlative nature of this study, and in doubtful cases, the peak was put in the "unclassified" section. The author welcomes correspondence on any errors which are found by readers, and hopes that such helpful criticism, as well as the increased availability of high resolution spectra — e.g., (3) — will largely eliminate such errors in later editions of this table. Empirical Formula. Only the ion of m/e of the most abundant combination of isotopes is classified. If there are multiple possibilities In Mass Spectral Correlations; McLafferty, F.; Advances in Chemistry; American Chemical Society: Washington, DC, 1963.

INTRODUCTION

3

because of the presence of natural or artificial isotopes, the remainder are classified under P.I.D. Thus in a particular spectrum if the C H5 ion is the most abundant, the C C H15 ion could well be the fifth most abundant. It is not classified, as its significance is usually fairly obvious from the presence of the larger C H peak. In the case of elements with more highly abundant natural isotopes, however, this leads to some possibly unexpected classifications. Thus, the most abundant CHBr2 ion is not that containing two atoms of the most abundant of the isotopes, Br . Because the Br abundance is nearly that of the Br , CHBr2 gives ions of m/e 171, 173, and 175 in a ratio of 1:2:1. Thus, a spectrum giving rise to the CHBr2 ion would be referenced only under CHBr Br , m/e 173, and the corresponding isotopic ions at m/e 171 and 175 would be tabulated under P.I.D. This should cause no difficulty in the identification of CHBr2 from an unknown spectrum, as the largest peak should be used first to identify the ion. Structural Significance. Where possible, the types of ions causing the empirical formula shown are postulated, and the abundant compound types found are tabulated separately. The justifications for many such structural classifications are due to careful correlations of spectra that have been published by a variety of authors. No attempt has been made to give proper credit or reference to this vital previous work. Such an attempt would seriously complicate the table, and it was also impossible to give proper credit in every case. The author found most helpful a number of unpublished correlations which had been prepared informally by coworkers in the Dow laboratories. In addition, a sizable number of interesting structure-spectralrelations were found which are reported for the first time in this table. The theoretical implications of these new correlations will be discussed in separate publications. The author has had the temerity to make structural classifications andpostulate correlations in many cases without rigorous proof. This is partially based on experience and intuition, but it is presumed that a number of such postulations will in time be shown to be incorrect. It is hoped that in most cases these will serve a useful purpose, even if only to stimulate the reader to point out such errors. Where the assignment is in considerable doubt, a question mark has been inserted and, of course, the most dubious cases have been listed under Unclassified. If there appear to be two ways in which the particular ion in the spectrum could have arisen, it is usually classified under the most probable. If this isuncertain or if it is felt the ion would be considerably less abundant if only one such structural influence were active, it is listed as Unclassified. However, at most mass numbers there are few cases of this. At m/e 57 a further breakdown of overlapping mechanisms was attempted because of the very large number of C H ions found. Thus, a second number is listed following that indicating the number of tabulations under the most abundant, etc., peaks to indicate those compounds in which a second structural feature influenced the formation of this peak. For example, in fer^butyl ethers the high abundance of t h e C H ion is caused by the ready cleavage both at the branched fer£-butyl group and at the alpha bond of the ether. +

23

21

+

20

21

15

+

79

79


+

81

+

79

81

+

+

4

+

4

9


9


4

A D V A N C E S I N CHEMISTRY

SERIES

A homologous series of compounds will be expected to show similarities in structural correlations. Thus, when the classifications for a particular empirical formula were found to be parallel to a lower member of the homologous series, reference has often been made to this lower ion instead of making a complete listing of the possibilities. Since the higher member of the series is usually not represented by as many compound examples in the mass spectral file, it may be that one or more of the structural types indicated for the lower member were not actually found at the higher mass. At m/e 200 and above, individual compounds are often listed with the inference that by checking lower members of the homologous series analogous possible structures will be indicated. For the individual compound the postulated mechanism of formation of the particular ion is usually indicated, followed by "etc." where it is thought that the other classifications foundfor lower members of the homologous series will apply here also. For example, at m/e 223, the structure "Cl(H C ) PhCH(CH )-, etc." is listed. Indications of other possible structures can thusbe found at m/e 189 (which refers to m/e 133) and m/e 209 (which refer s to m/e 125) which list molecules in which CI- and CH -, respectively, are replaced by H - . Thus through these cross references one can infer that at m/e 223 such structures as CI ( H C )PhC (CH ) - and CI (CH ) (C H ) PhCH (CH )- are also probable. A number of ion types are placed under P.I.D. (Parent, /sotopic, Doubly charged) instead of being classified separately. It is felt that the parent (molecular) ion is not representative of a structural type, but only of a single compound or group of isomeric compounds. Thus, the usefulness of the molecular ion for structure determination lies more in the indication of empirical formula for the parent molecule and in indicating the structural groups of the molecule through the difference in mass between the parent ion and other prominent peaks in the mass spectrum. The peak at highest m/e represents the molecule ion when the molecular has sufficient chemical stability - e.g., unsaturated or cyclic structures. As a further check, the parent will be an "odd-electron" ion with an m/e of even number unless the ion contains an odd number of nitrogen atoms (2, 8). An ion containing a less abundant combination of isotopes, also included under P.I.D., is not classified separately because identification is usually more simple from the more abundant isotopic combination. The mass number and relative abundance of isotopic ions can be calculated from the accompanying table. It might be argued that classification of these could be useful where the more abundant isotopic combination is obscured by another ion of nominally identical mass. This, however, will be an unusual circumstance and can be overcome by careful use of the table or by the use of exact empirical structure determination through high resolution techniques. Multiply charged ions, a third classification under P.I.D., are rarely of sufficient abundance to be included. Those that were found usually offered little apparent structural significance in addition to the corresponding singly charged ion and were much less abundant, although further work in this field may show helpful correlations. The most common doubly charged ions of sufficient abundance were 7

3

2

3

3

n

3

2

2

5

2

5

3


3

2

INTRODUCTION

5


NATURAL ABUNDANCES OF COMMON ISOTOPES Element

Isotope and Natural Abundance (Most Abundant = 100%)

Hydrogen

i , 100%; 2, 0. 0156%

Boron

10, 23. 2% [25.0%, (12)]; 11, 100%

Carbon

12, 100%; 13, 1.120%

Nitrogen

14, 100%; 15, 0. 36%

Oxygen

16, 100%; 17, 0.04%; 18, 0.20%

Fluorine

19, 100%

Silicon

28, 100%; 29, 5. 07%; 30, 3.31%

Phosphorus

31, 100%

Sulfur

32, 100%; 55, 0. 78%; 34, 4. 39%

Chlorine

35, 100%; 57, 32. 7%

Gallium

69, 100%; 7i, 66. 7%

Germanium

70, 56.0%; 72, 75.0%; 75, 21.2%; 74, 100%; 76, 21.3%

Arsenic

75, 100%

Selenium

74, 1.92%; 75, 18. 2%; 77, 15.0%; 75, 47.4% S0, 100%; 82, 17.7%

Bromine

79, 100%; 81, 97. 5%

Tin

3.07%; 114, 2.08%; JI5, 1.07%; 116, 43.6%; iI7, 23.4%; 115, 72. 8%; 119, 26.5%; 120, 100%; 14.5%; 124, 18.3%

Antimony

i £ 2 , 100%; 123, 74. 7%

Iodine

127, 100%

Mercury

i96, 0. 54%; 198, 33.6%; 199, 56. 9%; 200, 77.7%; 201, 44. 5%; 202, 100%; 204, 23.0%

Lead

204, 2. 66%; 206, 50.9%; 207, 40. 4%; 208, 100%

Most instruments show some mass discrimination which tends to lower the observed abundance of the heavier isotope a few per cent. In Mass Spectral Correlations; McLafferty, F.; Advances in Chemistry; American Chemical Society: Washington, DC, 1963.

6

ADVANCES

I N CHEMISTRY SERIES

found in the spectra of fused ring aromatic hydrocarbons and generally arose from loss of one or more hydrogens from the parent ion. No metastable ions were found of significant abundance, but most of the spectra from the author s laboratory were recorded using a metastable suppressor to eliminate such ions. No attempt has been made to give the true structure of the ion, if it is actually other than that indicated by the nominal bond cleavages. For example, Meyer son and his coworkers (12) have shown that cleavage of the benzylic bond in aromatic hydrocarbons does not give the benzyl ion, C H C H , but the rearranged tropylium ion. Thus, the entry PhCH •£ R under m/e 91 indicates only the benzylic bond cleavage and not the rearrangement. Relative Probability of Ions. The final columns of the tabulation, headed 1, 2, 3, and possibly up through 10, show the number of compounds giving peaks of each relative magnitude under each structural classification. Thus, of the 212 compounds studied in which m/e 91 is one of the three highest peaks in the spectrum, 48 were found to be formed as the most abundant through the benzylic cleavage loss of an alkoxyl, alkyl, halogen, carbonyl, etc., group. Further, such a cleavage was found to produce the second and third highest peaks in the spectra of 18 and five compounds, respectively. Thus, one can draw the inference in attempting to identify a base (highest) m/e 91 peak in an unknown spectrum that one should first check for the possibility of the benzylic structure in the molecule. By similar reasoning a C H ion having a reduced intensity in an unknown spectrum would probably not arise from the C H C H - group, but from a more complex structure through a more drastic cleavage or rearrangement. The usefulness of this probability concept is admittedly in doubt, because the 4000 spectra cataloged, although a large number on the basis of known collections of mass spectra, are still only a small percentage of the total number of organic compounds in the literature. The distribution of structural types naturally depends somewhat on the interests of the originating laboratory and company. Thus, the large number of C H 0 C 1 ions tabulated atra/e 196 resulted from the study of a sizable group of trichlorophenoxy ester derivatives. However, the compounds of this file generally represent abroad range of chemistry, and a real attempt has been made to include also all classes of compounds whose spectra have been reported in the literature — e.g., steroids and hydrocarbons of high molecular weight. In general, the statistical data are probably meaningfulfor the" simpler" organic compounds, but of little value for more complex or specialized classes of organic compounds, such as plant pigments, perfluoroaromatic compounds, sugars, etc. Thus, the distribution of relative abundances should be given weight in structure indications generally only where quite a number of compounds of that type were available. For example, as cited above, the data for C H ions indicate that structures containing the benzyl ion have a high probability of giving this m/e as the highest peak in the spectrum. However, the absence of a large number of entries for C H S at m/e 123 does not indicate that the corresponding thiobenzyl(HSC H CH -) compounds could not give a very abundant m/e 123 peak. 1

+

6

5

2


2

+

7

6

5

2

+

6

3

3

+

7

7

+

7

7

6

4

2


7

INTRODUCTION

7

When several structural types are listed for the same formula on one line, they are generally in decreasing order of importance. SYMBOLS † indicates that this bond is cleaved to form the ion. The group or groups lost, if indicated, are usually designated by general symbols such as R (alkyl) or Y (functional group). Ph †R †H indicates the loss of the R group with rearrangement of one of its hydrogens to the resulting ion (here Ph-H ). This should be followed by "(rearr.)." Theβ-hydrogenatom is usually the one rearranged (7), so that the lack of aβ-hydrogenin the compound should greatly reduce the probability of the rearrangement. A double cleavage such as CH COO † R † H indicates the rearrangement of two hydrogen atoms, although in this case the second hydrogen atom need not come from the carbon atom beta to the bond cleaved (10). † indicates two bonds are cleaved (usually not the cleavage of a double bond). RC (R')(R") † indicates that the bond broken is to the carbon atom and not to R' or R". (ABC) † Y means that Y might be substituted on A, B, or C. "Base" means the highest peak in the spectrum — i. e., the most abundant ion. A semicolon signifies that the classifications following it are significantly less abundant than the preceding ones. Above m/e 218 in the table the semicolon means that the classifications following it were only found as less intense than the fifth most abundant peak. ΣR indicates a summation of the alkyl groups — i. e., if R = C H , R'=C H , and R"=H, then ΣR = C H . (C F ). Parentheses around a formula indicate a significant ion (especially for exact mass determination) which was not in the card file, and is therefore not included in the numerical tabulation.


+

3

2

3

2

6

5

3

9

8

ABBREVIATIONS aliph. aliphatic arom. aromatic cleav. cleavage corre sp. corre sponding cpd. compound dvts. derivatives esp. especially gp. group h.c. hydrocarbon mult. multiple Ph phenyl group P.I.D. Ions parent, isotopic, or doubly charged ions R hydrocarbon moiety (generally aliphatic, but can be a hydrogen atom) R* hydrocarbon moiety containing an electronegative group as X, - N 0 , -CN, -COOR, -COR, etc. (see Y* below) 2


8


rearr, rearrangement(usually of a H atom. If none is indicated, the location of the rearranged H atom is not definite), satd. saturated substd. substituted unsatd. unsaturated X any halogen atom Y a functional group Y one or more Y groups Y* an electronegative functional group, asX, - N O , -CN, -COOR, -COR, -S0 X, -C=CH, R*, -NCS, -COX, etc. Z another functional group or combination of several Y groups. n

z


2

CONCLUSIONS Despite the fact that this file cannot possibly contain a representative number of all possible types of organic molecules, the prevalence of certain entries is of interest. A total of 15,746 peaks from the spectra of 4036 compounds were examined, and an assignment of structure and mechanism was attempted for each of these. The most entries are found at m/e 43, 41, 57, and 55, representing 5.8, 5.5, 3. 5, and 2. 6%, respectively, of the total entries for the three most abundant ions. Similarly, the most abundant empirical formulas found were C H 5 , C H 7 , C H 9 , C H 7 , C H O , andC H7+, representing 5.3,4.0,3.0, 2.4, 1.5, and 1.5%, respectively, of the total number of entries for the three most abundant ions. Figures A, B, and C represent the number of entries which were found for the first, second, and third most abundant ions, respectively, at each nominal mass number. The number of peaks to which no appreciable structural significance could be assigned ("other unclassified") was gratifyingly low. Separation between peaks classified as P.I.D. and "other unclassified" ions was not made for all m/ebelow m/e 103, but these types together represented only 11% of the total, so that the "unclassified" alone should be under 5%. At the higher mass numbers the "other unclassified" ions were 9% of the total. The fact that such a high percentage of the major ions in this wide variety of mass spectra are explainable indicates the potential of the method for molecular structure determination, and the significant progress that has been made within the last decade on the fundamentals of ion decomposition paths. Space has been left in the table, especially at the higher m/e, for the addition of correlations found subsequently by the reader. This, of course, will increase the usefulness of the tabulation in the areas of the reader's particular chemical interests. The author would appreciate it if any such additional correlations could be forwarded for inclusion in a possible future edition of the table. To reiterate, it would be very helpful to hear of alternative explanations of mechanisms for the data shown or of any errors found. Often the neutral fragment lost is of as much structural significance as the ion formed. Thus it should be possible to construct a similar tabulation using the mass of the difference between the abundant ion +

3

+

3

+

4

+

4

+

2

3

7


INTRODUCTION

9


NUMBER OF SPECTRA FOUND

40 h 20 0 0

20

40

60

80

100

120

140

160

180

200

220

240

Mil. 260

280

Figure 1. Number of spectra in which ions of a particular m/e were the most abundant


10


360

-

340

-


NUMBER OF SPECTRA FOUND

60 40

-

20

-

0 0

20

40

60

80

100

120

140

160

180

200

220

240

260

280

Figure 2. Number of spectra in which ions of a particular m/e were second most abundant


INTRODUCTION

11

NUMBER OF SPECTRA FOUND -


360

0

20

40

60

80

100

120

140

160

180

200

220

240

260

260

Figure 3. Number of spectra in which ions of a particular m /e were third most abundant



12

ADVANCES

I N CHEMISTRY

SERIES

found and the molecular ion. With such a table, functional groups which ordinarily do not retain the positive charge on cleavage of the molecular ion, such as the methyl group, halogen atoms, etc., could be classified and more easily identified. Such correlations fail, of course, when the abundant ion is formed from a fragment ion instead of the molecular ion, but the incidence of such cases would be of interest. Preparing such tabulations with the file cards used in the present study should be simplified because degradation paths have already been assigned. However, the preparation of such a correlation should await an assessment of the usefulness of the present tabulation. In the past few years, the markedly increased use of mass spectrometry in the solution of complex problems in molecular structure has been most gratifying. It is hoped that this tabulation will encourage this use by directly aiding both the neophyte and expert in structure identification. Possibly of greater importance, however, isthedemonstration of the high percentage of the abundant ions in mass spectra to which meaningful structure assignments can be made, demonstrating the maturity of the method and the unique usefulness of its molecular structure information. ACKNOWLEDGMENT This paper embodies efforts and ideas of such a large number of personnel of the Mass Spectrometry Section of the Chemical Physics Research Laboratory of The Dow Chemical Co. That it should be called the "Dow Table" of prominent ions in mass spectra. The structure and principles of this table evolved from invaluable discussions with R. S. Gohlke over a period of several years. Among others whose contributions are gratefully acknowledged are Jo Ann Gilpin, Joanne M. Rupprecht, Marjorie A. Eash, William T. Shelburg, and Eugene O. Camehl. The author is also happy to thank Norman Wright and Victor J. Caldecourt for inspiration and counsel, Priscilla A. Turner for stenographic assistance, and Charlotte M. Cripps for tabulations.


13

INTRODUCTION

LITERATURE CITED


(1) Beynon, J. H., "Advances gamon Press, London, 1959.

in Mass

Spectrometry,"

p. 328,

Per-

(2) Beynon, J. H., "Mass Spectrometry and Its Applications to Organic Chemistry," Elsevier, Amsterdam, 1960. (3) Beynon, J. H., Saunders, R. A., Williams, A. E., Anal. Chem., 33, 221 (1961). (4) Colthup, N. B., J. Opt. Soc. Am., 40, 397 (1950). (5) Doederer, G. C., Olsen, R. S., Appl. Spectroscopy, 16, 25 (1962). (6) Kuentzel, L. E., Anal. Chem., 23, 1413 (1951). (7) McLafferty, F. W., Ibid., 31, 82 (1959). (8) McLafferty, F. W., "Mass Spectrometry," in "Determination of Organic Structures by Physical Methods," F. C. Nachod and W. D. Phillips, eds., Academic Press, New York, 1962. (9) McLafferty, F. W., Gohlke, R. S., Anal. Chem., 31, 1160 (1959). (10) McLafferty, F. W., Hamming, M. C., Chem. and Ind. (London) 1958, 1366. (11) Mass Spectral Data File, Committee E-14, American Society for Testing Materials, 1916 Race St., Philadelphia, Pa. (12) Rylander, P. N., Meyerson, Seymour, Grubb, Henry, J. Am. Chem. Soc., 79, 8482 (1957). (13) Shapiro, I., Ditter, J. F., J. Chem. Phys., 26, 798 (1957). (14) Von Hoehne, J., Users' Clinic, Consolidated Electrodynamics Corp., New Orleans, June 1958. (15) Zemany, P. D., Anal. Chem., 22, 920 (1950).


Correlations of M a s s Spectral D a t a

Publication Date: January 1, 1963 | doi: 10.1021/ba-1963-0040.ch001

, — I. 0078

H

2.0156

H

Structural Significance*

Relative Probability It ~ 3 3 If" 6 Total 1

2

1

P.I.D.-2

1

2 1

3.

4 0

4.

P.I.D.-l

1

5.

0

6.

0

7.

0

8.

0

9.

0

10.

0

II. 0093

B

12.0000

C

Small molecules

13.0018

CH

Small molecules

2

1

4

4

2

3

1

1

5

16 5

* For meaning of symbols, see page 7 of text; for abbrevations, see page. 7. t Number of spectra in which the most abundant ion has this m/e. 15



16

Structural Significance

Formula

14.0031 14.0156

1

N CH„ Unclassified Total

15.0235

CH

3

3

4

5

2 1

1 1

2 3

3

2

1 3 1 5

17.0027 17.0265

4 5 1 29

2 10 8 3 66

3

1 3

2

3

4

18.0106 18.0344

l I

P . I . D . and i Total

l l

1 3

2

P . I . D . and \ Total

l l l 3

4

2

19 19

26 26

21 21

HO H N 3

H 0 H N 2

4

(Data not meaningful, as no rigorous effort to remove H 0 from most samples. H 0 also from hydrates, thermal decomp.) Total

9 15 3 2T

5 2 2 24

1

2

3 7 2 5 12

2

3 6 4

1

O H N

7 Total

1 5 13 14 5 5

2

15.9949 16.0187

6

1 2 10 4 2

1 1 5

Hydrocarbons R4- Y (Y=-COOR) (Y= -COR) (Y= -OR) (Y= -NRa) 1 (Y= X , - N 0 ) (Y=-HgR, 2 -N=NR) 1 (Y= -OCOR*) Other compounds P. I. D. and unclassified Total T 1


2

4 1 5

3 3 1 7

8 7 2 17

1

5 8 2 15

1

2

2

18.9984 19.0184

F H 0 3

P . I . D . and unclassified Total 20.

P . I . D . and unclassified 1 1

21.

P . I . D . and unclassified

22.

66 66

P . I . D . and unclassified

1

1

1

1 2

2 _

1 4 1 2

1 1

1 1 2 3 5 _ _ 9 5 1

1


2

Mass

Spectral

m/e

23.0264

Data

m/e

14-28

17


Formula

1

Relative Probability 2 3 4 5 6

B H 2

24.0000 24.0343

1

Highly unsatd. h. c. Total


25.0078 25.0421

26.0031 26.0156 26.0499

27.0235

C H B H 2

2

3

CN

1

2

3

P . I . D . and unclassified Total

1

1 3

R-j-CN, RCHN i "

2 1

5 2

1 P . I . D . and unclassified 1 Total 2

~3

~7

8 9 1 _3 21

2 2

5

2 7

CH =CH-j-R Other h. c. C H = C H f COR, CH = CH + COOR C H = C H f X , CH = CH -f COOR X-j-CH CH=l=HY (Y= -COOR', X , etc.) Other compounds C H B H - , higher boron alky Is 2

2

1

5

6

1

2

3

2 1

8 16

5

P . I. D. and unclassified 2

3 2 3

1

8 2 6

1

43

13

63

4

2

1

2

2

2

27.0577

4

4

B H 2

5

3

Total 27.9949

CO

5

2

2

CH B

1

4 -1

1

2

C H

1

1

Highly unsatd. h. c.

2

27.0406

7 Total

Lactones (could be C HJ Other (also possible from action of 0 on electron filament) (N gas impurity is possible, although eliminated where recognizable) Ethylenimines 2 Alkyl amines, esp. (CH ) N2 Satd. h. c. 2 Dialkylaromatic h. c. Other compounds Unclassified ( C H , CO > or C H N 20 P . I . D . and unclassified 3 29 Total 2

2

10 19

2

28.0061

N

2

2

28.0187 C H N (or C H ) 2

2

4

3

28.0313

C.H,

2

2

2

1 8 20 1 3 1 2 5

30 3 4 7

20 33 3 6 43 69

73 12 141

4


18

m /e

ADVANCES

Formula

29.0027

CHO

29.0391

C H 2

I N CHEMISTRY

Relative ^Probability^


4 R - f CHO (R < C ) ROfCHO Epoxides Mixed ROR, ROH 1 C H + Y (Y= -CHRR', - C R R ' K ' ) (Y= -CH PhR) (Y= -COOR) 1 (Y= -CONR ) 1 (Y= -COR) (Y= -SR or -SSR) 3 (Y= -OR) 5 (Y= -OCOR*) 15 (Y= X) (Y= -ONO, - C X , , -ONO -HgR, -CNS, -N0 ,etc.) 5 Satd. h. c. 1 7 Cpds. with satd. h. c. moieties P. I. D. and unclassified 2 45 Total 5

5

2

5

2

4 2 2 5 2

2 2 3 23 5 2 5 1 4 1 5 3 1

8 6 4 32 6 3 16 1 9 6 12 23 3

2 1 5 9 59

3 2 32 10 104

10 4 44 21 208

4 1 1 7 10 5 5

3 2 1 2 6 1 5

1 7 4 4 35 19 6 10

2 2 2 39

3 2 7 32

5 8 15 114

4

17

21

14

16

48

6

5

17

1

9 6 2

2 4 1 8 1 1 10


2

2

29.9826 29.9980

H Si NO 2

H SifR Aliph. and arom. nitro cpds. R N + NO (nitrosamines) RONO, R O N 0 , etc. R-j-CH NH R f C H N H f R ' -f-H (rearr.) Combination of above RfCH N=j= (R' -j-H) (rearr.) R C H ( C H ) N H cpds. (m/e 44 is base peak) RCO -f- N H C H -f R (rearr.) P. I. D. and unclassified Total 2

2

2

2

30.0344

CH N 4

2

2

2

SERIES

1 1 2 26 3

2

2

3

2

f

2

30.9984 31. 0184

CF CH 0 3

4 6 43

R + C H O H (many of these cpds. have other possible sources of m/e 31) 18 R + C H 0 -f R f H (rearr.) (mainly ethoxides; dioxanes, etc.) 6 O Y - M - j - O C H 4 R ' (rearr. )(M= C, S, P, A s ; Y= RO-, R N H - , R C O - , R - P h - , etc.) 3 HCO 4- O C H 4 R (rearr.) (formates) 5 CH3O + OR, C H 0 - j - C O N H Cpds. having more abundant C H 0 peak (mainly m/e 59) 2

T

2

2

6

2

3

n

2

4

17

21

7

4

9

20

39

43

53

135

2 n + 1


2


Mass

Spectral

m/e

31.9721 31.9898

Data

m/e

29-37

19


Formula

Relative Probability 1 2 3 4 5 6 Total

S

o

( 0 gas impurity common, removed where recognized) 2

2

32.0262 CHF, CH N(?), P H P. I. D. and unclassified 6


9

5

9 6 25

4

5

2

1

2 1

6

2

1

1

1 2

3

2

6

8

"7

5 28

R - j - C S - N H (R = aromatic); C H SH P . I . D. and unclassified 2 2 Total

1 1

1 1 2

1 1 2

1 1

1 3 6 1 9

1

3

1 2

1 4

1 1

2 1 1 4

4 10 1 1 5 5 16

5

4 1 5

7 2 9

1

2 2 4

R-j- C H F Other (rearr.) HOCH -j-CH OR={=H (rearr.), HOCH + CHRR'4=H (rearr.)? 2

33.0340

4

2

Total 33.0140

5 4

2

2

4

3 12 1 6

1

1

2

2

2

H P (PH ), HS (H S) 2

3

2

P. I. D. and unclassified Total 33.9877

1

34.9689

CI

34.9955

H S

5

Small molecule, CI mainly on - C O - , S, P , - C N , - C X - , etc. CH SCH P. I. D. and unclassified Total 2

37.0078

2

2

2

35.9767

5

3

HC1

C«H

3

3

Cpds. with "active" CI (and chlorides, etc.).May be HC1 from thermal de4 comp. P. I. D. and unclassified 1 Total Highly unsatd. or halogenated small molecules (h. c., furans, etc.) P . I . D . and unclassified Total

1

1

1

1

20 3 23

5 ~5


7 14 4 ~7 18


20

T?nr.m la jormuia 38.0031 38.0156


39.0109 39.0235

C N C H2

Relative Probability 1 1 3 4 5 Total

RR'C^R^-CN Highly unsatd., halogenated, etc. small molecules (h. c . , furans,etc.) P . I . D . and unclassified Total

2

3

C HN C H 2

3


3

2 _1 4

C H C N (C,H ?) HC=C-CH f Y (Y = X , -H) 3 Dienes 2 Cyclic olefins, acetylenic h. c. Olefins 6 H *C H -j-COR C H Y, C H Y , R C H Y ( Y = X , O, S) 2 Furans Other heterocyclics (pyridines (C HN?), etc.) Aromatics (mainly d i - to tetra-subst.) Others 13 Total 3

5

2

3

3

3

5

3

3

4

C H N 2

2

R - j - C H C N , R-j-CH=CHN=tR (cyclic), etc. Dienes, acetylenes, cyclic olefins, etc. R C H Y (Y=-C1, -COR, S; R=H, - C H )

C H 3

4

6

3 4 13

5 1 1

10 11 8

15 12 15

14 2

10 8

24 12

1

15

16

1 31

8 4 83

8 5 127

1

3

3

2

f

40.0313

3

2

2

41.0027 41.0265

C HO C H N 2

3

41.0391

C H

1

5

OCBH, Q O ( C O ) 3

z


3 7

Nitriles, RCN Pyrroles Cyclopropyl -j- Y (Y=R, -COR) CH =CH-CH 4 R CH = C(CH )4R CH -CH=CH-fR Other h.c. Cpds. with h. c. moieties

4

1

2

2

3

1

10

4

8

16

1

3

5 2

2 3

3

4

1 11

1 13

5 38

1 4

1 11 2

1 4 1 12 5 2 3 3 1 3 2 9 27 38 95 24 105 237

6 19 7 14 160 366

2

3

5

4

3

Also:

12 _7 22

2

4

2

40.0187

6 _3 10

1 5

3

2

4 _3 8

3 2


Mass

_

Spectral

/

m/e

Data

m/e

21

38-43

Relative Probability 1 2 \


i T o ^ i i o

Formula

C H -j- Y (Y= -COR; -CN) (Y= -OR, -SR, -NR ) (Y= -OCOR*, -NRCOR*) (Y=X) ( C H ) B - , higher boranes P . I . D . and unclassified Total 3

5


2

41.0562

Co H B

42.0106 42.0343 42.0469

C H N C H

R

3

2

H | - C H C O f Br Ethylenimines, CH CH=N-{C H = C H C H f R f H ; cyclopropyl -|- R 4- H (rearrs.) Other h. c. Other compounds 2

2

4

3

6

3

2

Total

10

9

7

26

11

1

3

15

4 1 3 5 13 2 1 366 117 173

8 5 13 3 656

1 4

1 3

1

2 1 3

5 4 5

1 5 1

8 10 9

17

19

34

70

_2 29

24

41

_2 104

4 30 36 2 4

4 7 5 11

1 14 11 17 4

5 48 54 24 19

15 3 2

27 5 3 1 2 3 37

2

C H„ C H 0 , or C H N Unclassified P . I . D . and other unclass ified Total 3

2

2

2

43.0058

4

CHNO

CONH-fH,

R-O-f

R N -{- CONH 4- H ( ?) CH CO + R C H C O + OR CH CO + NR Cyclic ethers Other satd. ROH, ROR, mixed CH =CHOf R Other CH N=N-f C H Cyclic amines Other 2

43.0184

C H 0 2

3

3

3

3

2

5

2

43.0296 43.0421

CH N C H N

43.0547

C H

3

2

a

2

5

7

3

3

( 3^2 f W 2W+l CH

CH

C

H

Other ( C H j J o C H 4 R, (CH ) CHf RY C H C H C H 4- CHRR , -f-CRR R" (branched) C H C H C H f R (R= -C-C=C, -C-Ph) Other C H C H C H - | ^-WH Cpds. with large satd. h. c. groups 1

3

2

7 2 1 1

2 3 29

8

31

20

20

71

9

3

1

13

2

1

1

4

43

33

20

96

26

82

80

188

1

3

2

2

f

3

2

2

3

2W+3

2

2


22

A D V A N C E S IN CHEMISTRY SERIES

m/e

43.0547

Formula

C H 3

Relative Probability 1 2 3


(Cont'd.) C H - Y (Y= -COOR) (Y= -CONR ) (Y= -COR) (Y= -NR.) (Y= -SR or -SSR) (Y= -OR) (Y= -OCOR*) (Y=X) (Y= - N 0 ) P . I . D . and unclassified Total

7

3

9

7

2

5


44.0136 44.0262

CO

2

a

CH NO C H 0 2

2

4

Decomposition, as C O ; salts 2 3 R * - { - C O O H (or + R ' ) ? 8 H N C O f R, H NCO f OR 4 O C H - C H 4 R 4 H (rearr.) 1 CH =CH0 4 R f ( -) 2 Oxiranes, dioxalanes Other 10 H NCH(CH )4R R 4 CH(CH ) NH f R + H (rearr.) 3 5 CH NHCH 4 R R - j - C H N (CH ) -j-R f H (rearr.) 1 17 (CH ) N4CR Ph 2 (CH,) N + COR Cpds. having a more abundant n *i+i P 6 Other 6 P . I. D. and unclassified 70 Total 2

2

2

H

r e a r r

2

44.0499

CjjHeN

2

3

f

3

3

3

c

CH0 CHj. Si C ^ F C ^ O 2

2

2

7

9 1 6 31

16 7 15 141

7 1 5 7 10

10 11 3 1 2 5 2

15 11 12 2 8 22 34

4 11 9

2 4

3 5

4 16 18

3

3

1

7

7

4

2

13

a

H

N

e a k

1 Thiacycloalkane or R - S - R ' Y Thiophene dvts. 2 HOOC 4 R* CH SIR, - ? (by rearr.) 1 C H2 F 4 X , C H F 4 HOCH CH 4Y(Y=-OR, - N R , - S I 10 22 CH CH(OH)4R 3

2

2

2

2

2

2

3

CH CH (OH) 4 COOR, CHgOCEL-j-COOR

3 40

4

3

C H , O C H « 4- k

R 4 C H (CH3) O 4 R + T

R4CH

H

(rearr.)

(CH3)O4COCHY4H

(rearr.) (Y= H or R*) RO 4 C ^ CItj O 4 COR* (rearr.), PhO 4 Ctt, CEj O 4 C -CHR* 4 H (rearr.) etc.

4 11 16 7 3 5 8 11 4 5 8 18 3

4

3

A

44.9976 45.0060 45.0140 45.0340

2 4 1 1 1

13 2 6 1 8 16 12 5 2 27 692

3 1 1

1

CHS

4 7 2 1 3 6 1 1

2

2

44.9799

1

1 4 4 4 2 10 4 5 3 5 2 13 9 5 279 210 203

2

43.9898

4 1 1

Total


Mass

Spectral

. mje 45.0340

Data

m/e

„ , Formula C H O 2

B

23

44-48

Structural significance


C H N 2

7

45.9877

CH S

45.9929 46.0296 46.0418

OaN QJHJF C H«0

3

2

2

OP CC1 H OSi CH S

47.0132

CH 0

3

3

3

2

C H4F 2

7 8

6 5

13 19

10 86

14 5 81

3 1 60

17 16 227

3 3

2

7

2 8

H B 3

4

C HgSi(CH ) OH (rearr.) HSCH 4R HgCS 4 R R-CHaS-R' (rearr.) etc. R4CH(0 4CH CH ) (rearr.)? ( C H 0 ? ) CzH+F + R; CF CHClCF CH OH (rearr.) C H O C H 4CHROH, HOCH CHROH (mult, rearrs.) B H f H , B H -f B H P . I . D . and unclassified Total 4

3

2

2

2

3

2

3

2

2

3

4

7

4

3

SO , SOX^, etc.

48.0000 48.0034

C CH S

HC=CC=CH HSCHRCHJJCHO, R 4 SCHg - j - R ,

4

2 3

1 1 8 12 1 4 16 2 9 5 17

4 1 1

4

1

2

2

2 2 6

1

2

6

1

1

5

1 10

1 14

1 1 16

2 3 1 2 1 4 26 76

3 1 1

1 1

3

2

OS CHC1 H OSi 4

4 6

7

47.9670 47.9767 47.9931

4

2 1 2 4 3

1

2

1

2

47.0607

1 1 6

8 4 1 1 2 1 10 2 25

4

1

POClg

3

C H 0

5 Total

1

2

47.0496

6

2

46.9687 46.9689 46.9853 46.9955

4

2


47.0296

3

f

Cpds. having a more abundant C H ^ O peak Others ( H C ) N 4 C H P h (Y)-OH (rearr.) (m/e 44 i s larger) P . I . D . and unclassified Total

Mainly cyclic sulfides

2

2

(Cont d.) W

45.0578

1

8

10

w

PhOSi(CH ) 3

1 (rearr.)

3

1 5 4 7 1 1

1

3

1

5

2

5 1 1 3 6 23

F

H S C R j f CH OH (mult. rearrs.) B ^ ^ H g P . I . D . and unclassified Total 2

48.0685

H B 4

4

1 1 3

_2 7



Formula

CH C1 2


Relative Probability 1 ~i ST" 4 Total

C1CIL, 4 R Cl-fCHCl-j-R-f-H, 4CC1 + R 4 H (rearrs.) BF H C = C O H , HC=CCH=CH 2

BF C H «sB


4


CH C1 3

C H C l f C O O + H, C H C l f C O f H (rearrs.) F Y C Y (Y or Y = - X , - C N , - C X , -COR) N C - C ^ C - f - H , NC(-C=C-)Y (Y= - X , -CN) Unsatd. alkynes, Ph-Y* Pyridine-Y dvts. (Y= H, Y*) (C N?)

21

3

1

1

5 1 2 1 2 32

1 1 4

12

1

2

2

1

2

1

3

C N 3

2

4 1

2

CHF -j-R C X F 4 - R , C F = C R Y (rearrs.) NC-C R4:HCN 2

2

2

C HN 3

C H 4

3

2

_2 4

5 1 2

Alkyne dvts. Ph-Y*

Pyridine-Y* dvts. ( C H N ? ) 3

P . I. D. and unclassified Total

C H N C H 3

2

4

N C - C H = C H 4 R , etc. Alkynes, P h - Y , pyridine-Y (C H N?) P . I . D . and unclassified Total 3

C H N 3

3

2

NC-C H 2

4

J. 9

2

4

2

8

2 1

2

3 1 1 _2 10

1 24 6 _2 35

10

1

3 13

3

3

21

_2 35

7 4 2 4 25 7 _5 54

1 1

1 2 _2 _1 5 4

4

3 _2 6

_1 2

1 7 _6 17

AHCN,

3

2 NCC2H 4(H)OROH Alkynes, dienes C H 5 ^ H X , furans, etc. _1 P . I . D . and unclassified Total In Mass Spectral Correlations; McLafferty, F.;3 3

C Hg

12

4


CHF

7 1

3

3

1*6 B

4

1 10

2

2

2

4

7

1 1

2

4

C H

2

3

2

CF

7

2

1 5 4 _ 10

6 2 _ 8


3 11 6 _1 21

Mass

Spectral

Data

m/e

54.0469

C ON NC-CO-j-CHj 1 C H2 O Maleic anhydride C 3 H 4 N N C C H C H f Y (Y=-OR, - C H X , 4 -SR, X , H, -RCN) C H Alkynes, cyclohexenes, C 4 H 6 AS0 2 , 3 H N (H) ={=C H=j= (H) CHOH 3 P . I . D . ana unclassified Total 11 2

2

4

2

2

C3H3O

55.0421 55.0547

C H N C H 3

5

4

7

4

6

H C=CHCO-f R 4-R-cyclohexanones, others, etc. Imidazolines H C=CHCH(CH ) f R , H C=C(C H )|R CH CH=CHCH -{-R, 2

2

5

15

2 2 10

1 7

5 6 28

2

5

3

2

C H5CH=CH4R 2

Other alkenes Cycloalkanes Cpds. with h. c. moieties C H f OR C H f COR C H +HX C.^BfCH,)P . I . D . and unclassified Total 4

7

4

7

4

C H B 3

8

7

2

CH0 3

C

4

H

3 e C H 4

8

4 1

15 6 2

2

3

11

10 7 4 7 26 28 37 58 2 3 2 3 3 1 1 None 111 107

7 6 19 48 1 2 1

24 17 73 143 6 5 6 2

92

310

3 1

1 1

4 5

11 5 1

1

6

3

2

56.0262 56.0500 56.0626

6

6

55.0184

55.0719

Total 1 1

1

3

2




Formula

53.9980 54.0106 54.0343

25

49-56

3

N

CH - (C H )|R4H(rearr.) (m/e 41 is also large) 3 Other olefinic h. c. (m/e 41 is also large) 2 Methylcyclopentyl h. c. 7 Cyclohexanes, other cycloalkanes 4 H + C H C ( C H ) -fR (m/e 57 usually larger) 1 H - j - C H C H ( C H ) - { - R (m/e 57 large) 1 H - j r C H -j-Y (Y= -OR, -SR) 2 (Y= -OCOR, -OCOR*) 4 2 (Y=X) R - j - C H - j - Y (R = C H , C H ; Y= -SR, -OR, X , -OCOH) 9 Cyclohexylamine cpds. 4 Others 4 C H , C H Oor C H N unclassified 7 P . I. D. and other unclassified 1 In MassTotal Spectral Correlations; McLafferty, F.; 50 3

3

4

2

2

4

8

3

4

4

8

4

8

1

4

3 2 2

5 1

10 10 6

16

4

21

2 4 10

1 2 8 1

4 8 22 3

2

4 1 1

15 5 5

15 3 64

22 2 55

44 6 169

2

3

2

3

4

3

5

3

7

6


26


m/e

57.0340

CgÔ



Formula

CaHgCO + R CzHsCO-j-OR CgHsCO + NRa

4 14

3 2

8

Total

2 1

7 18 1

2

2

12

3 * 19+4

1 3+0

4

2 8 26

12+13 4+1

7+1 3+2

8+2 0+2

43 12

0+4 32

2+4 11

18 70

15

61

HOC3H4 4 R>

R-j-C H -0 + R | H (rearr.), C 3 H 5 O 4 C O R t

4

3

6 C H 6 H C H -fx Mixed ROR, ROH (CH ) CfC H Other ( C H ) C 4 CgHgCH (CH ) 4 w H n i Other C H C H ( C H ) + other HC4 4 C „ H Other cpds. with satd. h. c. moieties C H 4 Y (Y= -CHRR , -CRR R ) (Y= -C-C=C) (Y= -C-Ph) (Y= -COOR)

57.0704

C4H

2

2

2

3

3

w

2 W + 1

3

3


c

3

2

+

2

5

2+6 27

3

2 W + 1

37

9

16+5 2

8+2 1

1

4

9

!

M

1+1 1 1+1 0+1 0+5 13+6 8 4+5

(Y= -CONR2) (Y= (Y= (Y= (Y=

-COR) -NR,) -SR or -SSR) -OR) (Y= -OCOR*) (Y=X) (Y= - N 0 ,

-CNS, -OSO R, - B 0 R ) Cycloalkyl-OH,-NH (C H ?) P . I. D. and unclassified

1+3 1+1 0+1 2+1 1 0+1

36 3 1 3 1 7 3 6 25 15 10

1 2 4

5 12 10

3+2 1 0+1

1

2+1 5+1

2

z

3

2

4

2

9

2 8 4 193+49

Total

242

58.0293

C H NO

HCONHCH

58.0418

C H 0

CH COCH

2

3

4

6

2

1+1 2 2 84+13

61+17 4 1 7 78

97

4 R,

HON=C(CH,)4R 3

2

4R4H,

H 4 R + C H C O C H 4 R 4 H, 2

HCOCH

2

(CH )4R4H 3

(rearrs.) Other Added figure - e. g . , +4 - indicates number of com pounds in which an additional functional group could be aiding structural feature indicated as causing abundant C H - e.g., ( C H ) C } O R . +

4

9

3

3


2 12

9 21

Mass

Spectral

Data

m/e

57-60

C H N 3

Relative Probability 1 2 3 Total


Formula

58.0656

27

H N C H ( C H ) - f R, H N C ( C H ) f R, R 4 C (C )NH 4 R' 4 H (rearr.) H CNHCH ( C H ) 4 R , R + C H (CH )N(CH ) 4 R 4 H 3 (rearr.) 10 (CH ) NCH 4 R 2 C H NCH 4 R 5 R 4 - C H N ( C H ) 4 R ' 4 H (Rearr.) 2 RC04N(C H )CH 4 R Cpds. having a more abundant C H N peak Others P . I . D . and unclassified 34 Total

8

2

2

5

2

3

2

2

3

3

f

3

3

2

2

3

2

5

2

2

2

4

5

T


2

M

58.9829 58.9955 59.0133 59.0297 59.0371

CNHS C H S C H O C H F C H NO

59.0496

C H 0

2

3

2

3

3

4

2

z

5

2

7 1

12 6 8

35

29

98

1 2 3 1

1 3 2

1 3 13 5

2 1

10 17 6

2 W + 2

SCN 4 C H 4 H (rearr.) Cyclic S cpds. CH OC0 4 R * 2

4

7 2

3

H NCOCH 4 R 4 H ; 10 HON=CHCH 4 R 4 H (rearrs.) 13 HOC(CH ) 4 R 5 HOCHfC,^) 4 R R4C(CH ) O 4 R 4 H , R 4 C H ( C H ) 0 4 R 4 H (rearrs.) 3 CH OCH(CH ) 4 R 7 C H OCH 4 R 5 3 C H O C H C H 4 OR 6 HOCH CH ( C H ) 4 0 R HOCH(CH )CH 40R Cpds. having a more abundant C H Opeak Others 1 CH NHN(CH )1 B B H , etc. P . I . D . and unclassified 12 75

2

2

2

7

3

5

3 10 2 15 3

3

2

2

!

3

a

f

5

2

3

2

5

2

3

2

2

3

2

2

3

w

59.0609 59.0778

C H N B H 2

T

5

4

2

2 W + 1

3

3

60.0211

R4CC1=CH4X Cyclic sulfides, H4(SC H )40R, etc. C H 0 H O O C C H 4 R 4 H (rearr.) H -j-R4CH COO 4 R ' 4 H (rearr.) R +OCH CH 0 4 R ? C H N O H O C H C H N H 4 COR, H NCH CH (OH)4R In Mass Spectral Correlations; McLafferty, F.; 2

4

2

4

2

2

2

2

2

2

60.0449

2

3 1

3 3 1

1

6

2

2

3

7 7 16 5 7 4

_9

1 1 _4

4 4 2 2 25

40

23

138

2

3

1 2 1

5 16 3 3

3

3

5

C HC1 C H S 2

8 1 1 1

1 0

4

Total

59.9767 60.0033

4

3

1

4

4 8 2

6 3

2

2



28

m/e

60.0857

Formula



4 Total

i 0

H B + H6B B , etc. B H P . I . D . and unclassified 5

5

4

5

U

Total


SERIES

60.9845

C H C1

61.0009

CH OSi

2

1 _2

_5

_6

1 13

18

14

15

47

CaHjjClfYjjR, C H , C l 4 - Y (Y=X, N 0 2 ) H C + S i ( C H ) O f (CH ) (Y)=J=H (Y = R, -CH COR) (rearr.) ? CHgSCH -|-R HSCH(CH )-R, R + CH(CH )s4R fH (rearr.) HSCHgCHg + O R R - S - R ( R > C or subst. C ) , (rearr.) etc. C H C O O f R + H (rearr.) Other a

2

5

3

3

3

11

2

2

61.0112

C H S 2

5

2

3

f

3

3

2

61.0289

C H 02

61.0453 61.0935

C H F B H +B B H , etc. 5 P . I . D . and unclassified Total

2

3

5

3

6

5

6

9 2

2

i q

4

62.0156 62.0190 62.0242 62.0367 62.1013

P C H C1

_4 27

P Y -j-(C H Cl)-j-Y' (Y= mainly ci, r=x, - O H , -COR, -CXRH) 4 C H Ph-Y (Y= I, - N 0 , - C O O C H , -NHR) CaHeS C H S + R + H (rearr.)? CH4 0 N HaNCOO + C H3 =f= H2 (rearr.) C He0 C H 0 0 - f C H , f H (rearr.) B H +B B H , etc. B H , B H P . I . D . and unclassified _2 Total 6 2

2

2

2

1 _5 60

16

1

2

2

5

2

2

5

3

3

15

3

2 1 2

5

2

2

1

3

3

2

1 _1 17

4

3

5

7 7 4 3

7

B

61.9475 61.9923

1 4 3 2

1

2

1 3 3 1 1 1

1 0

5

7

4

8

5

9

5

U

JL 10

1 _1 6


1 8

2 __4 30

Mass

Spectral

m/e

Data

C1-J-S1C1 + ( C H )

62.9358 62.9638

SiCl COC1

62.9705 62.9904 63.0001

CFS CH SO C H4C1

3

2

-j- Y (Y= X , -OR, - R X , etc.)

3

C HF s°3

3

3

2

2

23

3

1 1 1

3 2 1

_6

_6

18

45

6 _7 14

2 _1 10

9 14 39

3 2 1 3 4

2 1 3 2

7 4 2 6 6

_1 14

18 _4 30

18 _6 49

2

H + R 4 0 C O O + R=f H

C H

7 1 1

2

CH -SOfCH 1 C I C 2 H 4 + Y , (Y= X , - R X , -COB, -OCOR, P , S, etc.) 14 C l - { - C H C l + R + H, etc. (rearr.) 1 C HF +X 2


4 Total

C1CO

2

2



Formula

63.0046 63.0082 63.0234

29

6046

2

(rearr.)

Y - P h - Z (Y= -OH, Z= - X , - N 0 , -OH), w =1-3 _ w

2

Total

63.9619

so

64.0079 64.0124

C H C1 C H F

64.0313

2

18

R + SO2+X, R + SOz+R', inorg. (S also possible) C H C H C l 4 - C O O + H (rearr.)? X + C H F f Y (Y=R, X , -RX) Y - P h - Z (Y= -OR, -NHR; Z= X , -COR, - C N ; or YZ = fused heterocyclic ring, as in benzoxazole) 1 P . I . D . and unclassified _6 13 Total 2

2

5

2

2

C H

4

5

65.0202 65.0391

2

H F H 3

5

2

3

2

2

2

4 C H cpds. Subst. vinyl furans PhCH Y O NPhY (Y= -OH, -CH ,-CHO) Y - P h - Z (Y = -OR, NHR, -SR; Z=X, H) _1 P . I . D . and unclassified 5 Total 5

6

2

3

z

65.9598 65.9673 66.0469

HS2 CC1F CsH 2

6

1

H + R + SS + R + H (rearr.)?

2

1 3

1

4 4

4 1

2 1 1 1 9

3 3 1 2 10

9 5 3 9 34

1 Y - P h - Z (Y= -OR, -NHR, -SR; Z= mainly H, C H ) Methyl pyridines 1 Other highly unsatd. h. c. P . I . D . and unclassified 5 7 Total 3

1 8



SOF

CHC1F

FS0 4 (sulfuryl fluorides) FC1HC 4 R> also rearr. Alkynes, alkadienes, cycloalkenes, bicyclic h. c. R 4 Y (R= cyclopentyl, cyclohexyl, decalinyl, etc.; Y= R , -OR') P . I . D . and unclassified Total


T

CgHaON C H N C He 4

6

5

CF,

Relative


Formula

NCCH C0 40R NCC H 4 R Cyclopentane dvts. Cyclohexene dvts. Cyclohexanols, others P . I . D. and unclassified Total

1

2

3

3

2

3 4

3 9

23

12

6

41

4 _1 31

7 _4 25

21 _1 35

32 _6 91

2 2 2 1 6 _5 18

1 1 6 2 _2 12

3 3 12 5 8 13 44

4 6 6

2 4 2

2

3

6

4 4 _6 14

F C 4 C = C Y (vinylic) Other C F 4 C F by rearr. CH CH=CHC0 4 0 R , C H = C(CH )C0 4 0 R , cyclopropyl-CO 4 R> 2- or 3 -R-cyclohexanone H O C H 4 R (pentynols) C=C-C ( C ) 4 R , C H CH (CH )4R C -C=C-CH 4 R Cyclopentyl 4 R Other C H f R Other h. c. or cpds. with h. c. moieties q 3

3

26

3

C H 0 4

5

2

3

5

3

2

2

5

ON

4

Q,H N C H a

5

ir

9

C H 4 Y (Y=X, -SR, -CR) (C H ) B4R P . I. D. and unclassified Total 5

3

9 38 15

2

25 3

3

4

cH

3 3 7

3

2

C4H10B

4 Total

9

2

5

2

C H C (CN) (OH)R 4 C H N H C H 4=HOH; pyrrolidines (CH ) -cyclopentyl h. c. Terminally branched-C H , e.g., C H C ( C H ) (m/e 71 also large) 3

2

3

3

5

5

9

2 3 2 5

9 10 6 1

1 2 2

1 2

11 14 11 10

15

18

17

12

62

2

7 1 21 227

5 _3 78

1 _5 75

_6 36

_7 38

1

1

5

2

2

14 3

3

3 4

1

5

4 9

2

3

5

10

X 1

r


Mass

Spectral

m/e

Data

m/e

Formula

67-72

31

Structural Significance 1

70.0782

C H 5

1 0

(Cont'd.) Other h.c. H + C H 4-Y 5

(Y= -OR, -SR, -ONO) (Y= -OCOR, -OCOR*) (Y=X)

10

?

Others C H , C H ON, C H N Publication Date: January 1, 1963 | doi: 10.1021/ba-1963-0040.ch001

5

70.0871

71.0497

1 0

3

4

4

Probability 2 3 1 3

4

2

1

3

3 3 3

7 2 1 1 5 5

12 5 13

7

3

10

_6 38

1 _3 24

1 _9 81

unclassified

8

1 0

B B H , etc. B H P . I . D . and other unclassified Total 5

5

C HTO 4

6

1 0

19

W-C H CO + R 3

2 5 2 1 4

1 4

4 2

3 10 2 6 4 8 11

2 3 12

7 24 13

1 7 10

10 34 35

3

4 3 1

4

8 7 3

7

w-C H CO+OR

4

7

3

( C H ) C H C O + OR 3

71.0860

C H B

U

2

Tetrahydrofuryl -{- R Methylcyclohexanols Mixed ROR, R O H C H C (CH ) -C H C H CH(CH )-j-R, (C H )2CH-{-R Other satd. h.c. Cpds. with satd. h. c. moieties C H - ^ Y (Y= - C H R R ' , -CRR R ) (Y= -COR, -COOR) (Y= -OR; -ONO) O (Y= -OCR*) (Y=X) 2

3

5

7

3

2 W + 1

5

M

5

6

2

5

6

3

5

SCNCIL, -j- R. N C S C H 4 R (CH ) NCOfR H N C O C H C H + R , where R large, (m/e 59 is base) OCHCH(C H ) -|-R + H (rearr.) C H C O C H f R + H (rearr.), others 2

3

2

72.0575

C H O 4

s

5 11

3 4

2 4

3

2

2

1

2

7

_1 29

_3 45

J. 63

_5 37

10 174

3 4

2

1

6 4

4

2

6 2

2

5

9

3


3

2

3

3

4

CglijNS C H NO

1

1 0

B B H , C H B (OCH )-, CH CO-CO-, C H S, C HgN, C H N O 3

71.9908 72.0449

1

U

T

Also:

5 4 2 1

1 1

3

2

5

W

4 Total

2

2

2

2

5

5

1 1

2

2



32

m/e

72.0813

C^H^N

Relative Probability 3


Formula

4 Total

CH NHCH ( C H ) + R , C H NHCH (CH )4R, C H NHCH2 4 R , R 4 QHgN ( C H ) 4 R 4 H (rearr.) C H N H 4 COR Cpds. having more abundant C H Npeak 3

2

2

5

3

7

5

3

v

S

4

9

M


2 W + 2

etc. I P . I . D and unclassified Total

72.1028

73.0289

CHgCOOCR, 4 R (?) HOOCC H 4 R (rearr. ?) (base forR>C*) l,3-Dioxolanes4(2-R) C H Si (CH3) Si4R C H 0 B ( C H 0 ) B f Y (Y= R, -OR, X) C H O N (CH ) NCO 4 OPhR 4 H (rearr.) ? (m/e 72 is base) C HQO HOCH (C K,) 4 R , HOC(CH )(C H )4R CÔCI^-fR CH OC (CH ) 4 R , CH OCH(C H )4R, C H O C H (CHg)4R CHaOCHjjCH (01^)4 OR, HOCI^C ( C H ) 4 OR Others C H N (C H ) N 4 C H P h R 4 H (rearr.)? (m/e 58, 30 larger) P . I . D . and unclassified Total

C H 0 3

5

73.0653

3

9

2

6

3

3

2

3

7

2

3

4

1 4

5

5 7 6 3

5

3 1

13 7 7 3

1 2

3

3

2

3

2

5

2

n

C H S C H O 3

6

3

6

2

5

2

2

3 4

6 6

3

1

6

2

2 6

3 _5 29

3 20 87

1 1

2

1 3

2

HSCaHgiSHj,, cyclic sulfides HOOCCH (CH ) 4 R 4 H, CH OOCCH2 + R 4 H (rearrs.) CHgCOOCR, 4 R Y - J - H (Y= -OH, -OR ) (rearr.) Others HOC H N H C H 4 R> HOCH C (NH ) ( C H ) 4 R , R 4 C H N (C H OH) 4 R' 4 H (rearr./, C H N H C H C H ( O H ) 4 R , etc. P . I . D . and unclassified Total

10 28

_5 23

1 2

3

1

z

3

3

11

1

C HgNO 3

2

5

5

3

4

1 2

2

3

74.0605

1 15 58

_8 18

2

3

74.0190 74.0367

1 _5 25

4

3

73.0891

_2 15

2

2

73.0373 73.0461 73.0527

7

2

4

1

13 2 1 2

3 3

2

2

2

2

3

1 1

2

3

4

4 _3 18

2 _5 9

_4 8


1 1 8 _2 14 9 44

M a s s Spectral

Data

m/e

4

3

C1(C=C-C)+Y -OCOR)

(Y= -OR, - N R

C H C1^HXY

(Y=X, -COR,

3

75.0046 75.0166

C HF C H OSi 3

2

2

7

4


C H C H7 S

75.0445

C3H7O.

6

3

3

2

2

3

2

3

C2H ON 7

2

1

11 3

1

1 5

1 15 1

3 21 5

1 1

2 1

1

5 6

4

2 1

2 2

8 3

1 4 23

2 25

1 8 91

1

5 3

2 5 5

2 3

2

3

8 3

1 6 13

4 4 11

11 3 25

16 16 55

2

5

2

2

2

2

4 1

2

2

S

3

1 2

2

2

75.0558

2

5 -OCOR), C g H ^ l ^ X g CnHpK^ (q>p) HOSi ( C H ) + R , C H + S i (CH ) 0 +R-j-H 1 (rearr.)? P h f HY * C H 3 S C H - j - R ; HSC(CH ) 4-R 4 CHaSCH (CHs)+R, 2 HSCH ( C H ) + R 3 (CH 0) CHfR HOC H*OCH +R, H O C H C H ( O H ) f R, etc. C H C O O f R4=H (rearr.) R 4" CH (NHCH OH) N H 4 - N H C H 0 + H (rearr.) 1 P . I . D . and unclassified 30 Total 3

75.0235 75.0268

Relative Probability 1 2 3 4 Total

C H4CI -f- R

C H C1 3

33


Formula

75.0001

72-77

4

5

2

2

2

75.9441

CS

75.9999 76.0034 76.0080

C NF CH O N C H C1

2

2

2

2

3

s

5

Thiols, sulfides, etc., prob. from cracking on M . S. filament. N C C F 4-X O N O C H f R (nitrates) C H C1=£HX 2

z

3

5

3

C H 6

1

(Y= H, CI,

5

etc.; T= -COR, -OR, -OCOR, -R) 1 Ph + HY* Y 4- P h 4- Y (Y, Y = variety of substs. or Y - Y = fused arom. ring) 3 P . I . D . and unclassified 6 Total

4

1

2

Y +C H Cl4.r 76.0313

1

1 13

1

1

t

76.9794

C H O C l C1CH C0 4-Y (Y= X , -OR, R); CCl CH OH 4 C H C1 C H C1 -f Y (Y= X , -COR, R, -OR) 7 2

2

2

3

77.0158 77.0203

3

6

C H F 3

3

3

2

2

C H F + X , C H F f HYX (Y= X , -RX) 3

3

7

4

13

6

3

2

3

3

2

2

2

1 4


7


34

77. 0265 77. 0391

C.H3N

Relative Probability "~2 4 Total


Formula

Pyridyl =f=HY* Ph Y (Y= variety of subst.) o-Y-Ph-Y (rearr.) (m/e 7 7 » 7 6 ) m-, />-Y-Ph-Y (rearr.) (m/e 77 > 76) Others (unsatd. h . c , indoles, etc.) P . I . D . and unclassified Total

13

2 33

66

2 112

2

8

8

18

3

13

16

2 6 _4 7 55 111

8 11 194

1


T

78.0344

C H4 N

78.0469

CgHe

5

28

Pyridyl -j- Y (Y= -COR, - X , -CH=CHR, -NHR, -R, etc.) Ph-f-Y.+ H (Y= metal-R, -NHNH ; unsatd. as -C=N-, -C=C-; -OR, -SR) (rearr.) YCH fPhfY (Y=-OH, - H or fused to Y ; Y* = -OH, - 0 - , -CO-, - N 0 , etc.) (rearr.) Cycloalkadienes, substd. cycloalkenes P . I . D . and unclassified _7

12

2

13

T

2

1

2

Total

78.9671 78.9676 78.9751 78.9949

17

(C1CH ) SI(CH ) CH3SS + Y (Y=CH , -SCH ) C HClF-{-Cl C HC1F C H 0 P OPH(OCH ) + O C H , C H O f PO(CH )0+CH (rearr.) C H O C l CICHgOCHg -j-R? CH SiCl CH S 4

3

2

2

3

2

3

1

12 _6

12

14

1

1

18

3 21 61

1

3

1

2

4

3

2

3

3

78.9950

2

2

1

2

3

3

2

4

CIC4OC H CI4R|H 2

79.0422

C Hg N 5

3

(rearr.) Pyridyl-Y + H (rearr.) (Y= -COR, -CH=CH-) Pyridyl- (CH ) Cycloalkadienes, alkenynes Cyclohexenyl -j- Y, cyclopentenyl-f Y (Y= -COR, - C ^ O H , -CH=CHR, - C N , -R); polycycloalkenes, -anes Ph -f CH (OH) Y (rearr.) (m/e 79 > m/e 77, m/e 107 usually> mje 79); PhCH (NH )Y(rearr.) 3

79.0547

C H 6

7

1

1

1

2 1

1 5

4

5

3

12

1

7

1

9

W

2

5


Mass

Spectral

, rnje 79.0547

Data

m/e

77-81

_ . Formula C H 6

35


1

Relative Probability 2 3 4 5 Total

(Cont'd.) Y - P h - Y (Y= H , Y = -OCOR, -OR; Y = C H ,

7

1

t

3

Y

, =

- X , -CH2X; T

Y= - C H O H , Y =X) (rearr.) P . I . D . and unclassified 2


Total

79.9754 80.0027 80.0262 80.0500

CH S CH 0 P C H 0? C H N

80.0626

C

80.9907 81.0340

4

2

5

2

5

4

5

6

H

6 8

CH3SS + R + H (rearr.) C H . O O P H - f OCH, (rearr.) Methy lhydroxybenzene s Alkylpyrroles, subst. pyridines and anilines Subst. cyclohexenes Cyclohexyl-YT, - Y T Y " (Y=X, OH, *-bu, etc.) Satd. multiple fused ring cpds. P . I . D . and unclassified Total

_3

3 _5

7 10

10 18

16

27

29

72

2 8 1

4 2

1

1

1

1 3 7

1 7 18

4 13

C H C1F C H C l F - f Y 3 C H 0 Furan-CH fR 5 HOPhY (Y= -OR, - N H ) C H N P y r r o l e - C H -f R + H (rearr.); R-pyridineNH 1 C HQ Alkyl hexynes; hexadienes 2 Cyclohexenyl -f Y , polyisoprenes 7 2

3

2

5

5

5

7

1

1 1

2 9

1

17 5

2

5

3 1 8

5 17 55

3 7 5

2 5

2

2

2

81.0704

4 2

3

2

81.0578

1

2 1 3

6

C y c l o h e x y l ^ H Y Z (mainly Y= -OH, Z= R, or YZ= fused ring) 10 Cyclohexyl-Y, - Y T Y " , etc. 4 Also: H O C H C F - , C H O C F - , B C 1 , C H F C O + OR + H (rearr.) 2

2

2

3

2

5

1 4

1 1

4 12

2

3

1

13

16

9

6

41

4

6

1

15

1

5

2

2


1

3

1

_1

_2

_5

_6

14

36

31

35

17

119



36

m/e 81.9377 82.0656 82.0782

Relative Probability 1 2 3 4 5 Total


Formula

SERIES

CC1 4=XY (Y= - C H [ O R ] , 3 2 2 2 -CHO, - C N , X , etc.) N C C H C H C H C H -f R 1 1 C y c l o h e x y l ^ H Y (Y= R, substd, 8 8 19 7 R; -OR, X , etc.) C y c l o h e x y l ^ Y Z (mainly Y=-OH 4 3 2 Z= R) etc. P . I. D. and unclassified _4 _6 _5 J8 16 29 18 22 Total

CCL,

2

2

2

C

6^L0

2

2

9 2

2

42


;

82.9455

9 23 85

4 4 12 3 CHCL 4 - Y Cl-j- C C 1 - j - C O - R f H (rearr.),> 4 3 2 (impurity?) 2 F S 0 \Y (Y= X , -OR) 4 1 1 1 1 1 Thiophene+Y (Y= X , -COR) CjjKjFg 4-Y 1 4 2 F - P h - Y (Y= -OH, -OR, R, 4 1 3 -NH,) Dihydropyrans, alkenones, 2 alkynols, etc. 3 1 20 18 7 14 9 7 3 5 5 2 4 4 A l k y l - Y , - Y Y (Y= -OH, X) _3 _2 _4 _3 P . I. D. and unclassified 59 43 35 36 Total

CHCla

23

2

82.9603 82.9955 83.0108 83.0297

11 6 3 7

2

C H S 4

3

C ^F 5

83.0497 83.0860

8 6 59 24 15 12 174

1

84.0034 84.0375

C H S Cs^F

84.0813

C H N

4

5

Thiophene + C Hjj -f H (rearr.) F - P h - Y (Y= -NH2, -OR) (m/e 83 large) Piperidines, methyl pyrrolidines, imidazolines 6 (rearr.) Alkanes (m/e 85 large) C H + H Y (Y=X, -OCOR, -SH,etc), C H +(OH) 3 (-CHjjOH) 2 Others 2 P . I . D . and unclassified 13 Total

1 0

84.0938

6

SiF POF CC1F C H5 0

1 2

2

1

1 2

1 1 6 12

2

CC1F

2

2

3 1 2

4 1 3 9 12 16 24

1

3

4

1

1

2

8 7

1 2

6

84.9621 84.9655 84.9657 85.0289

1

2

4

2

(rearr.)

19 1

1 5 2

13


9 7 11 40 16 81 1

1 1 37 3

Mass

Spectral

m/e

Data

m/e

Formula

85.0653 85.0765 85.0891 85.1017

C^HeCO + R, C H C O + OR Cyclopentanols, others Piperazine 4-R 4

C H N C H N 4

f l

5

2



9

1 1

U

0 3 ^ 0 ( ^ 3 ) 2

5 Total

3 1 1 1

-j-R,

CH C(C H ) -fR 4 C H CH(CH ) +R, 6 C , H , C H ( C H ) -j-R 1 Other satd. h. c . , etc. 2 C H 4-Y (Y= -COR, -COOR) 2 (Y= -OCOR*) 2 (Y= -OR) 4 (Y=X) 16 6 P . I . D . and unclassified Total 25 51 32 S

4

2

5

9

2

3

a


37

82-87

6

86.0731

C H 5

1 0

O

1 3

CH3 COC (CH ) o+R+H, CgHyCOCHj + + (rearrs.) RO + C H O f H, etc. 3 (C H ) NCIt +R, C H NHCH (CH )+R, C H NHCIfe -j-R, etc. 14 R + CHaN ( C H ) + Y (Y= RCO-, P h C H - ) (rearr.) 3 Others 1 P . I . D . and unclassified 5 26 14 Total 3

R

5

86.0969

C H N 5

1 2

9 4 2 3 4 4 22 108

B

2

5

H

2 14

1 0

2

3

7

4

9

3

4

1

2

87.0001

C H C1

C H C1 + X , C H C 1 1 HX, ,

C H S C H Q2

C H C1 +H X Thiacycloalkanes CaHsCOO + R + Ha (rearr.) CH OOCC « +Y,

4

4

4

4

4

87.0268 87.0446

4

7

7

4

4

4

2

3

2

18

f l

_3 6

8

3 3 25 11 65

4

3

1 3 3

4

C H 3OOC -cyclohexyl-Y

(rearr.)

3

C H 3 C O O C H (CH )-j-R

87.0530 87.0616

C H Si

87.0809

QJHJUO

4

u

Other esters and acids Methyl dioxolanes, etc. C H ( C H ) Si + R 2

5

3

8 3

3

3 4

1

2

3 1 2 1

15 5 6 8 2

C J H Q O J J B C-HÔBt+OR) -O-f-R + H

(rearr.) ROCR'R" 4 Y

2 (SR= C H 4

Y= R, -OR) HOCRR' f Y (SR= C H 4

1 0

u

)

,

6 2


14 8

ADVANCES

38


Formula

2

5

2

3

4

5

1 3 16 9 19 40 25

9 19

2 5 16

3 42 119

1

1

1

6

1

1

2

5

1

1

2 2

4 1 8

1 2 7

13 11 39

1

(C H ) NCH -j-R + H (rearr., 86 is larger) P . I. D. and unclassified Total

87.1047


2

6 Total

2

C H 3 O O C C H (NH )-,

88.0398

2

CH OOCCH(NHf COR) 4 R' + H (rearr.) C H OCOCH + Y + H (rearr.) (Y= R, -OR, -COOR) HOOCCH (C H )-j-R + H (rearr.) Others Z fCYNY'Y", Z - f CYN (Y ) + Z + H (rearr.) (2Y= CgHjOH, Z= -R, -CRÔH, etc.) P . I . D . and unclassified


3

88.0524

2

5

2

88.0762

C ^ C l C ^ C l +X C H OOSiR SiR , C , H O S i -RCH ROCH SiR 22

C H 7

(

5

2

4 2

2 2

8

8

2

3

2 4 8

5

3

2

89.0391

1

l

Total

Q

2

5

t

89.0158 89.0322

1

2

(rearrs.)

3

Z

=

8

,

1

1

1

3

6

N H

( ^ X ? " "' - C H - ) , PhCHYY , YPhCH Y , PhCH Y, Y P h C H , Y -(Ph-C) (Y=X, - C N , - N 0 , etc.) C H SCH fR ( C H 0 ) C (CH ) + Y (Y= -OR, R), T

2

T

2

2

3

3

2

89.0425 89.0602

C H S C H 0 4

4

9

9

3

2

7

2

3

2

2

1 1

3

3

1 2 2

7

7

22 1

40 4

3

HOC3 H O C H -j-R, 6

2

HOC H O C H -j- OR, etc. C H C 0 0 4-R + H (rearr.) P . I . D . ions Other unclassified _2 Total 6 2

3

7

4

2

4

2

5 4 2 15 2 1 5 3 5 7 1 18 J _2 J . J 7 12 10 22 24 26 100


Mass

Spectral

z m/e

90.0344

Data

_ , Formula


C H N 6

39

37-92

m/e

Relative Probability 1 2 3 4 5 6 7 8 Total

YPhNCO, YPhNHCONH , YPhNHR (Y= - N 0 , X) PhCH Y*, CH PhY*, benzo cpds., etc.

4

2

3 1 1 1 1

2

90.0469

C H 7

6

2

Also: C H C l 4 = H X , C H C H O 4

4

7

4

1 0

4 6 3 4 4 5 8


C H C1 C H N C H 4

8

6

5

1 1 1 1

7

7

1 3 1 3 1 2 1 1 1 1 1 1 10 10 9 8 8 6 10

C 1 C H + R; C 1 C H + O R 7 1 PhN=fHY; Y + PhNH + Y ' 3 3 3 P h C H + Y (Y=-OR, R, X , - R X , -COR etc.) 48 18 5 C H P h f Y * , C H P h + C H 13 1111 PhCH + YY* -j-H, 4

8

4

8

3

3

P h C ^ Y =f=H (rearrs.) (Y=R; X , -OR) Combinations of above (rearr.), etc. 3

2

P . I . D . ions Other unclassified Total

CeBÔ

92. 0500

C H N 6

6

13 3 62

8 9 71 35

2

ClCHjjCILjCO-hOR, (N0 ) -j-PhOfR 2

92.0262

4

2

3

Also:

34

S,

1 0

2


91.0314 91.0422 91.0547

1 8

3

18 9 7

34

2 7 27

36

1 1 3

5

6 _2 _5 _1 94 54 64

HOPhY ( Y = - N 0 , -COOR, large R, X , -OH, etc.) 3 2 4 PhNH + Y (Y= -COR,-NH ), U N P h f Y ( Y = X , -COR, -COOR) 2 4 5 CHg -pyridyl -f Y (Y= - C H , -COR, H), pyridyl-CH -{-R 12 5 PhCH -fR4H, PhCH„-j-RY 4 H (rearrs.) 12 7 5 4 PhCH +(OR-j-H PhCH fNRYfH, P h C H + S R f H (rearrs.) 1 5 4 9 PhCH=CHCH OR, (rearr.), ^-pinene, etc. 12 1 P . I . D . ions 4 1 1 4

6 8 212

2

9

2

11

3

2

92.0626

C H3 7

8

2

2

28

;

2

2

19

2


4 10

40


m/e

92.0626

92.9340 92.9952 93.0107

Formula

C H 7

8


(Cont'd.) Other unclassified Total

CH Br


J. 19

B r C H + Y (Y= X , R, - R X , etc.) C F Halocarbons and dvts. 5 C H O C l C 1 ( C H ) C (OH)-j-R, C1C H4 0 C H + R 3 C HsO HOPh-f Y ( Y = - N R , -COR, - N 0 , X) C H N P y r i d y l - C H -f R f H; Y f p y r i d y l - C H -j-R (rearrs.) 2 PhN(-j-R) -j-Y, P h N H - f Y (rearrs.) (Y=-COR, -N=CR, -NHR, R), N-Ph-dihydrobenzoxazines 5 C H Terpenes ( C H ) ; cyclohexenyl-Y , - Y ; sesquiterpenes 12 2

3

3

3

6

2

_ _7 18 39

_12 101

7 5

10 18

3 8

5

2

6

1

4

2

2

93.0578

_4 25

Total

2

2

93.0340

Relative Probability 1 2 3 4

6

7

1

5

3

9

2

2

93.0704

7

9

1 0

C3H3CIF,

5

3

3

5

16

4

1

1

18

1 6

2

Also:

1 2

3

C H 0 C1, 2

2

2

RPO (OR) OCH3 (rearr.),

C1(CH3) S i f R 2


93.9419

CH Br

94.0418

C H 0

2

2

2

6

4 _1 19

1 2 _1 22 27

35

B r C H f Y + H, R - f B r C H f Y [Y= -COOH, - C O H , - P h (X) N 0 ] (rearrs.) 5 PhO-j-Y-j-H (Y= R, -COR, - R T ) (rearr.) 15 Y * + PhO-j-Y, HOPh + Y , benzopyrans (rearrs.)

3

2

8

2

5

2

6

6

Also:

13 2 103

C H SS -f R -j- H (rearr.), HOOCCHC1 + R 4 H (rearr.), C H P O (OCH ) 4 OR f H (rearr.) C H , C HF , C1 C=C4 2

5

1

27

5

5

1

13

5

3

7

6

3

1 0

3

3

2


6 5 31

3

3

1 _2 _2 12

8


6 _4 9

60

Mass

Spectral

m/e

Data

m/e

Formula

95.0133

C5H 0

95.0497

C H 0

3

41

92*97

Irrelative Probability 1 2 3 4 5


Furyl-CO-j-Y (Y=-OR, R); furyl-CH(OCOR) 7 PhOH ? [ from PhOC(CH ) , (CH ) CPhOH, Ph(OCH ) , ROPhYY (Y=X, -CHO)] Methylfurans, cyclohexenones, etc. Dienes, cycloalkenes, dicycloalkanes, etc. 9

2

2

6

7

2

3

3

3

3

C H 7

U


Also:

2

3

3

C H 7

2

33

3

2

4

4

3

3

19

1 2 3 9 7 _1 1 _2 23 22 16 24 21

23 4 106

5

4

1 0

3

2

C H C1

97.0112 97.1017

CsHgS C H

2

3

2

1 3

5

2

1

22

5

2

4

18

4 10 4 3 7 1 _1 1 1 _2 11 20 10 13 12 8

29 _5 74

3

C H C l 2 f Y (Y= X , - R X , - N 0 , - R , -COOR) Thiophene-CH^j- R CHgCeHxn f Y , alkenes, 0 ? H =pHY 2

3

2

7

5

2


96.9612

6

5

C H C 1 , furyl-CHO=|=Yr, C H C N , F P h f R f H (rearr.), C H F 3 2

1 2 7

6

5

9

5

1

2

2

7

Dicycloalkanes, cycloalkyl=f=HY (Y= -OH, R) etc. 3

1 2

Also:

3

3

3


96.0938

2

5

2

2

2

12

2

C H F , C H C1F, FPh-fY*, -HSeCH -,CH OS02 f OR, C HC1 -, CH -pyrazole-CH 3

1

3

1

95.0860

4

6 Total

13

Also: C, H 0 , 9

2

CF CO3


2

4 3

6 2

18 13

12 11

4

7

34

6 8

1

2

1 2 _3 _5

2 _8

27 14 14 22

77


42

m/e

98,0969


Formula

C H 6

1 2

N

Also:



3

C H O (cyclohexanols,etc.), furfuryl alkanoates, C HC1F , C H , thiophene-CH + R + H (rearr.), piperazine ^= R 6

1 0

2

1 4

2

2

1

2

2 _2

P . I . D . ions Other unclassified


98.9813 98.9846

C H C1F

99.0082 99.0446

C4H303

2

1

2

7

3

2

C H O 6

3

3

15

4 10 3 12 1 _3 _4

31 10

9 20

64

2

2

2

4

3

99.0809

2

H =f=R4-OPO (04R + H) (rearr.) Maleates, fumarates CH COC H CO-j-R, CH COOC H +R 1,1-cyclohexyl = ( O C H ) , C H -tetrahydropyran \ OR, C H CO -f R, C H C O + OR RR R"CfC H (R, R ' , R " not = H, 2 R = C H ) Other satd. h. c. C H f Y (Y=X, -COOR) 2

5

6

10 10 15

Total

C H 0

6 Total

C H -piperidyl -J- , etc.

7

2

SERIES

3

4

2

u

2

3

u

99.1173

C H 7

5

n

?

1 5

w

2

+ 1 6

7

Also:

1 5

1EL

Imidazolone-CH -, C H N , C H C 1 ( C l P h X N H , CIPhXOH), C l S i H + R, C H N (methylpiperazines), S C1, 2

5

6

4

1 3

2

2

5

n

2

2

7

3

21

P . I . D . and other unclassified _1 _6 _6 _6 _6 _4 Total 8 16 15 13 9 12

29 78

so ci 2

99.9936 100.0080 100.0762

C F 2

C C

5 5

100.0888

C

6

100.1126

C

6

Perfluoroalkenes, -cycloalkanes Others H C1 C l - P h - Y (Y=-OR, -SR) H N O ( C H ) NCO-f R 4-R-morpholines H O Cyclohexyl-0 f R f H (rearr.), R O f C H O f H, etc. H N RR'NCR^R™ f , where LR=C H Other amines, mainly (w-C H ) -NCH CHROH

3

2

4

1 1 2

2 1

5

1 0

2

5

2

2

1

2

1

4

1 2

6

1 2

1

1 4

5

4

1 4

9

2

2

1

5 2

1 1


8 10 4 3 6

Mass

Spectral

7

m/e 100.1126

Data

m/e

43

98-102

„ , Formula


Relative Probability 1 2 3 4 5 6" 7 Total

!

C H N (Cont d.) RCO-j-N (CsHu ) C H | R (rearr.) 2 Unclassified A A A A A A Total 10 11 9 9 13 16 6

1 4

2

100.9361 101.0391

CC1 F C H

101.0425

CgHgS

101.0602

C H 0

16 S t y r e n e ^ H Y (Y= X , -N0 ) Thiacyclohexanes, methy lthiacyclopentane s, etc. 4 R O C R ' R " 4- Y (2R= C4H 0),etc. 2 CzHgCOOC.H, f ,

2

8

5

1

3


9

2

9

CgHgOCOCgHi f ,

101.0966

C H 0 6

etc.

5

13

PC1 , PSF , CHgSi^Hg-, C HF , C H OB (C H )0-, (C H 0) B-, C HeCl, CF S, andC H N 2

4

2

2

5

5

2

2

5

1

8

1 3

2

1 1

6

2

2

6

2

1

6

1 3

1 1

6

3

2

5

1 4

10

A A A A ™ 32 17 13 13 17

Quinolines (loss of RCN), etc.; P h C H 4 = Y Y , Y Y «f P h C H f HY, etc. (Y= X , - N 0 , - C N , H, R) Ester, etc., rearrs. (see m/e 74, 88)

6

1

5

B

Unclassified Total

C H

28

2

2

102.0469

3

R O C R ' R " -|Y, HOCRR'-fY (XR=C H )

1 3

Also:

5

2

2

5

3

2 20 68

28 92

t

2

1

2

3

2

102.0680

C H O 5

1 0

Also:

2

C F C O N ( C H ) -|- R f H (rearr.), R-j-PhCN, C (CN) 3

2

2

5

2

4

1

2

7

2

6

22 4

2

1

3

Unclassified Total

2

A 1

1

1

A A A 7 7 7

3

4

8

1 _ 6


11 40


44

m/e

103.0394 103.0479

Formula

Strucutral Significance

5 Total

C ^ O g CH COOCH CH CH (OH) f R C H O S i (CH ) S i C H 0 + R, ( C H ) S i (OC H )-j-OR? C H P h C H + Y (Y=-C0 R,-COR, X , R); highly unsat. h. c . ; 3

4

n

8

7

2

3

3

2

2

2

3

103.0547

ProbabUity 2 3 4

2

2

2

5

2

2

(^Cjl

PhCHCH(-j-Y)-j-6,

(Z=NH, O, =C=0), PhCjjH^HYT, Y+PhC H 2

1

6

5

1

9

22

4 5 1 1

11

9 2

29 4

3


f

103.0581 103.0758

C H S C H 0 5

n

5

n

xfHY (Y = X , -OR, R), etc. C H S C H ( C H ) - f R , etc. HOC H OCH(CH ) f R, (C H 0 ) C H -j- OR etc. P . I . D . ions Other unclassified Total 3

2

7

3

3

6

2

104.0262

Y + PhCO f Y (Y= -COR, - N 0 , H; Y = -OR, R, X) P h - N(CH =j=) -f , p y r i d y l - C H - , CPhN Tetralins, indanes, Ph-cycloalkenes, -anes, PhCHYCHgY ( Y o r Y = X , -OH, -OCOR, Ph, R, H), etc.

4

f

2

104.0500

C H N 7

6

104.0626

C H

8

2

8

2

1

Also:

1

6 17

2

38

4 1 3 20

3

5

5

2

2 1 13 3 3 25 1 1 5 20 26 106

1

C H 0 7

3

5

C H C1, C H OS 5

9

4

8

P . I . D . ions Total

Subtotal, m/e 1-104,

1 1 3

4 2

17 1 8

,

11

8

1

1

13

4

5

A A A A A 19 21 24 10 14

41 2 20 88

2335 2312 2503 732 313 120 17 10 8342


Mass

Spectral

Data

„ *°

105.0340

m/e

,

45


r m u i a

C H 0 7

703-706

1

Relative Probability 2 3 4 5 6 7 8 Total

PhCO-fY (Y= R, -OR, -OCOR, X , etc.) 34 2 Y^PhCO-Y (rearr.), PhCH 0-Y, Y - P h O H , etc. 1 9 PhCH(CH )-j-Y, CH PhCH + Y (Y= R, X , -OR, etc.), C - P h + Y (Y= X , C H ) 4 5 PhCh=CH-fCH OR4=H (rearr.), others 8 15

5

36

1

2

5

15

6

15

13

36

1

9

1 1 4 37 29

6 9 126

w

105.0704

C H 8

9

3

3

2

2

3


2

2

Also:

C H N, C H Br, C H 0 C1 7

7

3

2

2

2

4

2


106.0418

C H 0 7

6

HO(CH )

5 4 60

4

Ph(4H)

3

HOPh(-f-H)CH fY (Y = OH, - C O N H , Ph) H N P h C H -j- Y , etc. 6 PhNHCH -j-Y; H4R4NHPhCH + Y (rearr.) 10 YCO -fNHPhCHg-f- R (Y= R, -RZ) (rearr.) 13 CH -pyridylC H 4 R , etc. 3 PhCH NH-, PhCH (NH ) + , H N (CH )Ph + X , PhN ( C H ) f COR, Ph-lactams, etc. 7 2

2

106.0656

C H N 7

8

2

3

2

5

3

1

10

2

2

2

2

12

3

3

19

9

1

13

3

2

2

2

2

3

3

3


10

ADVANCES

46

m/e

Relative Probabilit


Formula


"5 106.0782

Co Hi

CH PhCH-j- Y - j - H , PhC (cyclo-R)-j-Y-j-H PhCH (CH ) + Y -j- H (rearrs.) 1 3

6

6

13

3

2

6

6 3 3 _4 _2 _1 48 40 19

12 7 107

3

Also:

C H Br=j=XY, Pyridvl-CO2

C H Br^Hy,

3

2

3

1



107.0497

5 Total

C7H7O

HOPhCH -j-Y (Y=R, -COR); 2

H O P h C ^ R , HOPhCH=|=R (rearrs.) 4 HOPh(CH )+Y* Y4-OPh(CH )4Y* (Y= R, -RY) (rearr.); CH PhO + RY (108 is larger) 2 Y-j-OPhCH f T (Y=R, -COR, X) (rearr.); PhOCH -f Y (Y= -COR, - R X ; 94 is large) 5 PhCH (OH) 4-RY; P h C H O f RY, Y-fOCHaPh-j-Y (rearr.), XfPhCH OH 9 3

2

19

3

3

15

3

2

2

14

2

1

21

2

C H Br, C H 0 C1, C H N, HSC H O C H j-OR, linolenic acid, C l C H S i ( C H ) + R , C H N

Also:

2

4

3

2

4

4

2

2

7

2

6

7

3

2

C H ON 6

6

7

20

4 2 12 _2 _3 _1 38 42 33

18 6 113

4

2


108.0449

9

4

H NPhOf C H , RCO f NHPhO f R (rearr.), pyridyl-CHOHf C H P h O - f Y - f H (Y=R, -COR, -RY*) (rearr.) P h C H O -{-Y-J-H (Y= -COR, - C H C H ) (rearr.), P h O C H + R O H (rearr.), C -quinones 2

2

9

5

!

108.0575

C H 0 7

8

3

z

2

2

3

2

2


Mass

Spectral

m/e

108.0575

Data

m/e

Formula

1 0 6 - 7 70

47



C H 0 (Cont'd.) Also: C H S (benzothiazoles, HSPh f Y), B r C H . f COOR (rearr.), C H S S f R + H (rearr.), R-pyrroles 7

6

7 Total

8

6

4

2

3

7


C H C1 3

3

C H Cl -j-HX , C H Cl -j-X HOPhO-|-R, C H - f OPhO + R + H (rearr.), C H - f u r y l - C O H NPhO -j- Y -f H, HOPhNH -f Y -f H (Y= R, -COR) (rearrs.) SeeC H (m/e 95)

2

3

3

2

3

109.0289

C H 0 6

5

2

2

2

1 26 _8 64

9 5 3 4 5 JL_2J._J._3 18 17 8 10 11


108.9612

3

2

3

2

6

1 1

1

4

8

3

3

109.0449

C H ON

109.1016

C H

6

8

7

1 3

7

Also:

C C1F , P h S f , FPhCH f , R f PO (OC H ) -O f R + H (rearr.), ClPh=£ H X , C H 0 7 3

2

2

7


110.1094

C H

6

8

6

1 4

Also:

9

6

n

2

7

6

4 4 _2 25 18 13

HOPhO-f-R-j-H, HOPh(fY)-0+R (rearrs.) C H C H ( f H) -f-OR, etc.

2

5 8

5

2

C H 0

7

1 1 3 4 1 3

n

2

110.0367

2

2

3

20 2 2 6

10 _4 62

1 1 1

6

3

2

2

1

1

1

2

3

3

2

2

10

T

C H O , ClPh=j=YY , C H S e f R f H (rearr.) C H C1 , CBrF 7

1 0

2

3

5

4

2


5 8 4 2 5 1 4 JL 2 _2 _3 2 12 12 11 9 11 1 8

American Chemical Society Library 1155 16thCorrelations; St., N.W. In Mass Spectral McLafferty, F.; Advances in Chemistry; American D Chemical Society: Washington, DC, 1963. Washington. C 20036

9 29 10 64


48

m/e

Formula

111.0001

C H4C1

111.0268 111.0446

C H S C H 0


CIPh-f Y * , C l P h ( f Y ) + CHROH (rearr.) 2 9 CH -thiophene-CH -j-R Adipates (RO-j-COC H CO={= (H)OR?), 2 etc.

6

6

7

6

3

7

2

1 5

3

5

3


7

2

2

C H4 0

112.1126

C H 7

1 4

112.1251

C H

1 6

5

3

N

U

3

2

3

3

4

113.0014 113.0238

C HF C H 0

3

3

5

C H S i C l - , H-j-R-fCH SiCl -f (rearr.)

2

3

2

2

11

5

7

12

35

1

2

25

14

1 1 _5 _2 26 24

5 _7 89

1 3

4

2

2 1 3

C H C H 7

8

1 3

3

2

1

12

6

7

7

8

14

13

2 __1 7

12

12

30 1 58

4 2

1 1

2

7 3

2

0

6

1 7

Also:

7

1

3

3

113.0966 113.1329

3

5

Furyl-COO-fR4=H (rearr.), CH OOCCH=CHCOCyclic ethers, C H C O C H -f X

3

4

2

4

5

6

4

8


CH SiCl

1

1 6

FPhO-j-R + H (rearr.), C l P h - | - Y * - | - H (rearr.), C F , - C O C H C O - , etc.

112.9281

2

2

8

Also:

1

2

2

8

23 13

2

Furan-COO-J-Rf H (rearr.) (m/e 95 is base), etc. CH -piperidine-CH -}-R, cyclohexyl-N ( f R f H ) CH 4-R,etc. H f C H f Y (Y= -OCOR, -OH;R)

3

5 3

2


112.0160

10 1

7

C H , C H C 1 , (CH ) -boroxinf R, C H C 1 F , C H B r F , C H O, OP (OCH ) + R f H , thiophene-CO -f 8

5 Total

6

2

4

Also:

Protebility 2 3 4

8

1 7

(CH ) -piperazine-, C H B r F , F Ph-, C H F, CF S-, C C1F 0, C H C1 0 3

2

2

2

1 4 1 2 1 1 2

1

1 3

2

2

2

2

3

3

2

1

1

3

2


1

8

Mass

Spectral

/ m/e

113.1329

114.0918

m/e

Data

, Formula

C H 8

1 7

, ... Structural Significance


115.0547


(Cont'd.) P . I . D . ions Other unclassified Total

6 Total

3

_5 _1 12 5

C H ON HO-RN(CH f)C H R 4:HOH (2R=C H ) C H N S e e C H N (m/e 100) 3 P . I . D . ions 1 Other unclassified Total 4

4 2 5 _6 9 13 13

9 17 52

T

6

1 2

2

3

114.1282

49

1 7 7-7 76

7

C H

1 6

6

2

2

7

1 4

Indenes, (CH =CH-) Ph Naphthyl-Y (Y=-OR, - N R , R) P h C ^ Y , PhC H YY , indanyl-Y, Y P h C H Y (Y= X , -OCOR, - N 0 , Ph, R, etc.) 4 P h - P h - Y (Y= -OR, - N 0 , -OCOR), P h - R - Z , etc. C H 0 Aliphatic esters, etc. (see C H 0 ^ 1 C H O N C H N C O C H -j-R-j-H (rearr.) 2 C H 0 ROC (R'R") f Y , HOCRR -f-Y ( S R = C H ) 1 9

7

2

2

2

2 4 1 1 1 _3 6 6

1 3

4

4

4

2 6

1 3

2

3 17

5 18 13

4

44

6 12

19

6

2 2 1 5

2 10 12 __5 29

n

3

3

f

3

4

2

2

115.0758

6

u

6

1 3

7

1 5

5

115.0996 115.1122

1

2

4

9

2

1 0

1

6

Also:

C H C1 F, 2

2

1

2

4

1

1

4

1

1

3

2

2

15

CgH^N

1 1

2

P . I . D . and other unclassified __ _6 _6 _5 _3 Total 9 21 31 34 22

115.9641 116.0500

C C1F Q H N 2

6

3

Y + C H P h C N , P h C H ( C N ) f Y, Y + PhCH CN, PhCYY'CN (rearr.) (Y= R, X) P h C H 4 H Y , PhC H 4: YY (Y=X, R, - N 0 , - N H ) , etc.

1

1

2

4

1 1 2

I

l

l

21 117

1 3

2

2

116.0626

C H 9

10

T

8

3

3

3

2

3

2

6


5 14

50



Formula

116.0626

C H

8

116.1075

C H

1 4

116.9066 117.0704

CC1 C H

9

6

9


Probability "5 5 4 5

6 Total

(Cont'd.) Naphthyl-Y (Y= -NHR, -OR); quinaldines 1 3 2 2 8 NO Amino alcohols, ethers 2 1 3 P . I . D . and other unclassified _5 _2 _5 _3 _4 _3 22 Total 9 7 9 9 14 12 60

11 C H (PhC=C)-j-Y, C H PhCK +Y, PhCH=CHCH -f Y, indanyl-j-Y (Y= R, X , -COOH, etc.) 17 ( P h - C ) 4 * H Y r ; (PhC )=fcH Y (Y=X, R, -OR, etc.) 1 S e e C H 0 (m/e 103)

3

9

5

6

1

23

6

30

5

11 4

1

6

2 2 1 _1 _3 35 16 19 18

9 5 88

3

2

3

2

2

3

117.0915

C H 6

1 3

0

Also:

2

3

5

n

2

2

5

3

5

C H 9

1 1 3 5

P h C H =f=HY (Y= OR; R, fused ring), PhC H =j=YY (Y= R, X ) ; Y + CH PhC H4 4 Y 2

1 0

3

5

3

5

1

2

Also:

6

5

1 2

8

C F C H 0 2

8

5

7

1 6

1 4

16

6

14

8 1 2 5 2 1 _4 _2 _2 11 10 14 6 13 10

25 9 64

8

2


118.9920 119.0497

2

2

C H 0 (misc.), C H N (misc.); C H 0 N 8

3 4

3

4


118.0782

2

2

POCl , C HC1F , C F , C H 0 (maleate) 4

7

2

(m/e 69 usually base peak) CH PhCO-j- Y ; dihydrobenzofuranfY Others

2

3

1

7

2

8

1

9

2 4

2 3

9 7

3

5


Mass

Spectral

m/e

119.0860

Data

m/e

Formula

C H 9

51

116-121


RPhC(R')+Y (2R=C H ), Ph (CH ) Others (multiple cleav., rearr.) (see C Hg)

n

2

3

C H4Br, C H O N , CH C1 , C H 0 3

7

7

3

5

2


C H4 0

120.0449

C H ON

7

7

6

7

34

1

5

11

5

1

1 21 8 106

1 13 1 2 34 42 30

Y-j-OPhCO-f-Z (Y= H, -COR, R; Z= -OR, H); dihydrocoumarins H NPhCO-fR, Y-j-PhNHCO-j-R, (rearr.), o - H 4 C H P h N O + 0, H NPhCOfY P h C O C H -f R + H (rearr.), PhC-(C-OH) + YH, HOPh (cyclo-R) -f Y , PhOC 4=HY See C H N (m/e 106) C P h +Y-j-H, CPhC (CH ) + Y + H(rearrs.)

2

21

3

2


120.0211

Total

7

4

8

Also:


9

3

2

14

3

1

1

2

7

16

2 7

6 4

1

8 28

2

1

3

1

1

6

2 7 7 4 _1 _2 _2 35 21 16 19

20 _5 91

2

2

2

120.0575

C H 0

120.0813 120.0938

C H C H

8

8

2

2

8

1 0

9

1 2

N

7

8

2

3

Also:

C H O B r (CH BrCOOR), PhSi(CH )=j=RR\ C H Br, CH ClCOOCH (CH )2

2

3

3

2

5

3


120.9289 121.0289

C H O B r B r C H C O f Y (Y=-OR, R) C H 0 HOPhCO + Y (Y= R, Ph, H, -OR); 0 N f PhCOO + R (rearr.), OHCPhO + R C H 0 See C H 0 (m/e 107) 2

7

2

5

2

3

2

1

4

6

6 4 7 8 10 15

17 33

6

16

2

2

121.0653

8

9

Also:

7

7

C H N , C H Br, C H (some monoterpenes, dvts.), (CH 0) Si-, C 1 C H 0 C H - , ferrocene In Mass Spectral Correlations; McLafferty, F.; 8

n

3

3

3

6

9

3

6

1 3

2

4

7

3


52


m/e


121.0653

Formula

C H 0 8


9

122.0367

C H 02

122.0731

C H

7

8

O

7

6 Total

7 9 6 2 1 2 31 25 33

PhCOO + R-j-H; R'CKDC+PhCOO-j-Rfrearrs.) See C H 0 ; HOPhCH(CH )fRfH (rearr.)

6

1 0



SERIES

2

22 5 99

1 2

5

8

3

Also:

7

8

2

3

C H 0 7

9

n

Also:

4

5

2

9

5

3

1 6

5

5

9

4 2 7

8 37 _5 63

2

10 7

5

1

16

2 2 3 _3 9 9

14 _7 54

3

2

1 2

2

7

4

5 5 _1 8 15 13

, CH PhCl4=Y , C H O , C H 0 , H NPhCl+HY P . I . D . ions Other unclassified Total 8

4 3 2 1 1 1 1 2

2


9

2

1

2

3

C H

2

C H C1 , C H , , C H0C1 , C H O P h N H \ (rearr.), C H B r F , O a N P h f Y f H (Y= -COOH, -OCH ) (rearr.), PhCH S + 5 3

124.

1

2

3

C H O 8

1

2

2

123.0809

1

6 11 9 2 _1 14 16 12

PhCOO + R + H (rearr.); (HO) PhCH -j-R, CH OPh(OH)+Y Sesquiterpenones, etc.

2

8

2


7

1 1 1 1

C H O N , 0 N P h f CHO, R-pyrroles, C H SS -j- R (rearr.), C H OBr 4 4

123.0446

4

8

1

z

2

3 2 1 4 3 1 1 1 8 6 2

2 5

2 4

7

6


3 3 1 7

13 19 _4 36

Mass

Spectral

m/e

125.0158

Data

m/e

53

C H C1

C l P h C H 4-Y (Y= R, X ) , CI (CH ) P h f Y (Y=X, -NO ), PhCHCl + R, etc. 16

6

z

(CH ) -thiophenyl-CH -j- etc., C H C1 , C C1 F, C H C1 C03

4

2

7

3

2

2

3

7

2


2

2

6

2

7

5

6

127.0359 127.0547

7

2

2

8 17 10 35

10 _2 12

6

3

12

2

1 1

7 3

2

7

Also:

C H OCOC H CO-, SF , CIPhO-j-R, C H C 1 0 , H-j-R-j-OPO (OC H ) 0 + R=|=H (rearr.) 2

5

2

2

3

2

2

5


C H 8

1 8

11

5

3

128.

3 10 55

_5 13

5

I Iodo compounds C H NC1 CIPhNH + COY + H (rearr.) (see C H N ) PhCF +R, C H F P h + R C H F Naphthyl f Y (Y= X , -COOH, Cin H -COOR) 6

17

6

3 _4 _1 27 15

ClPhCH + R - j - H , C H -thiopheneC H + R + H, C l P h C H + R + H (rearrs.), naphthyl =f= HY (Y= X , -COOH) 2 P . I . D . ions 3 Other unclassified _2 Total 7 2

126.9049 127.0188

25

2

2


126.

5 Total

2

3

Also:



Formula

7

727-728

2

1

9

4 6 6 _6 _1 _1 _5 14 22 19 16

16 13 71

2

4

2

N (seeC H N ) , C H O C l [ C l P h O f R | H , HOPh(Cl)-j-Y (rearrs.)], C H , C H N (quinolines) 1 4

6

1 0

8

5

9

6


23


54

m/e

128.

Formula

C H _ N (Cont'd.) P . I . D . ions Other unclassified Total


2

2

6

129.0704 C H 1 0

9

3

1 3

C3HCIF3+Y

3

4

9

7

C H B r ^ C l - f Y , (Y= X , R) C B r F + Y (Y= X , R)

2

1 7

Also:

R), etc.

7

2

7

16 _3 42

2

1 5 9

1 2

1 1 1 1

2

5

2

2

2

1

6 4

1 2

2

1 6

5 8

1

1

1 5 3

1

1 6

C ^ N , -CH 0S0 C1, C C 1 , (C H 0) B-; 3

5 3 1 _2 6 12 12

8

9

5

C H 0 8

(Y=X,

R O f COC H COO-j-R f H (rearr.) (adipates) 5 Indenes, R - P h - R (R= unsatd., cyclic) etc. Indanes, tetrahydronaphthalenes Esters, acids, etc. (seeC H Q2) H O C R R ' + Y (ZR = C H ) 1

3

129.0915 C H i 0

12

2

C3HCIF3

129.0551 C H 0

129.1279

6

6 Total

8

128.8931 C H B r ^ C l 128.9152 C _ r F 128.9719

1



3

3

2

1 6

P . I . D . and other unclassified _6 _5 _2 _5 _3 _5 Total 22 8 16 9 7 16

130.0656 C H N 9

Indole-CH -{-, methylindole-f-Y, C H C(Ph)(CN)fR 5 3 1 Ph-butenes, CH -indanes, cyclohexyl-Ph-, etc. 1 1 3 Amino alcohols 1 1

8

2

2

130.0782 C H 1 0

1 0

1 6

Also:

C HC1 , C H C1F 2

3

3

2

3


130.9920 C F 131.0497 C H 0 3

9

5

7

1

5

10

3

130.1231 C H N O 7

26 78

Ar

1 1

2

9 2 1 3

7 9 2 6 4 _1 _1 _3 _3 _1 _3 17 15 9 5 8 10

5 PhCH=CHCO + Y (Y=R, -OR); (PhO)C H 10 3

2

28 12 64

4

4

4

17

2

1

2

15


M a s s Spectral

m/e

131.0860

m/e

Data

Formula

C

10

H

55

728-733

Relative Probabililty "3 4


Tetrahydronaphthyl-, methylindanes, (CH ) (PhC=C) + Y (Y= R, X , etc.); (PhC )4HY

n

3

4

Also:

2

2

C H C1 , C H Br, C H 0 S i , C H Si , C H 0 2

2

5

1 5

3

4

2

4

7

5

1 5

n


C H 0 9

132.0938

C H 9

C

1 0

1 0

H

C=C-CPh (OH) =fe Y Y -COOR, R, H) (C=CPhCNH ) -}-Y,

N

1 2

3

1

2

6

13

_ 27

_7 17

_5 20

_5 23

17 87

1 3

1

1

1

7

8

6

5

7

2

1

1

7

2

2

8

8

t

4

6

2

1 4

1 1 3

7

2

6

2

2

1

2

2

4

3

12

_7 14

15 23

_4 9

_2 11

_5 9

33 66

C -PhCO -f Y ; 2,3-dihydrobenzopyran -f Y , etc. 5 P h O C H - j - Y , cyclohexylPh0 4-Y, C H P h O | Y , etc. 8 RPhC(R R )-|-Y (SR=C H ) 12 Others (mult, cleav., rearr.) (seeC H ) 2

T

1 3

8 8 5 3

7

5

tT

3

C C C C

1 1

4

8

Also:

1

(Y= X ,

C H NO, C C l F , C H 0 N , C H 0NC1, C H 0 , C H C 1

9

H

3

(CPhN-C-^) -j-Y, (NPhCC=C) 4-Y etc. (Y= X , -COR, R) 3 (CH ) PhCHCH 4=HOH, Tetralins, etc. 2

3

1 0

3

2

C H 0

C

25

yy

3

133.1017

6

C) ^ Y Y ,


9

9

0O+'*

Also:

133.0653

1

1

(PhC-

8

H8CH

132.0813

9

2

2


132.0575

5 Total

9

9

H ON (acetanilides), H 0 (phthalides, etc.), H 0 Si, C H Br, CF S , H F , C H N, C HC1 F

8 6

4 2

20 20

5

1

6

7

1

15

7

5

2

1 3 2

2

5

4

9

6

u

3

2

2

2

2

7



56

m/e 133.1017


134.0064 134.0605



Formula

C^H,


7

15 _5 88

2 10 3 _1 _1 _3 35 38 15

C H N S Benzothiazole f CI C H O N o - H 4 C H P h N O -j-O, PhN (CH ) CO -f R, CHgCONHPh -\ Y C H O, C H 0 , H - f OPh (CH ) CO -f OR, H + (PhCH 0) C H -j- OCOR, etc. 2 3 1 6 2 5 C H N SeeC H N P . I . D . ions 4 17 14 8 Other unclassified 2 8 1 13 22 26 16 Total

6 Total

4

8

8

2

4

3

134.0731

9

1 0

8

6

3

2

2

134.0969

134.9810

9

7

1 2

C H Br 4

8

2

3

8

B r C H f R (R>CH ), BrC H^fX 4

8

3

C H O 8

7

z

3

1

13

3

1

10

7

4

11

3

7

23

4 9 5 _1 _3 40 28 19

18 _4 87

9

4

135.0446

5

7 15 45 11 82

CH OPhCfY, HOPh(-CHO) C H + Y , HOOCPhCH + , etc. 6 PhN (COCH ) -j- R 4- H (rearr.), PhN (COCHz + R) + R (rearr.) [ PhN (CHR +• R ) -JC O R larger] See C H 0 ; PhOC ( C H ) f , P h C H O C H (CH ) + 13 3

2

2

135.0683

C H9 0 N 8

3

1

1

n

135.0809

C H O 9

n

7

7

2

2

Also:

6

3

PhSi ( C H ) -f , C l S i - j - , C C 1 F , 5 [(CH ) N] PO + NR 3

3

2

2

2

3

2

2


4

3


Mass

Spectral

m/e

136.0080

Data

m/e

lunula


C H C1 8

57

134-139

Cl-(PhC^)-j.Z (Z= Y , H Y C H , Y , HY; Y= X , -N0 ) Decahydronaphthyl- (137 is large), etc.

5

probSSy 1 1 3 V 5

4

2

3

2

1

2

136.1251

C

10

6 Total

Hi«

4

2

1

2

1

1

1

1

7

5

4

1

2

6

2

20


3 11

5

2

4

9 17

8

4 1 5 16

29 _1 64

Decahydronaphthyl-; etc.

7

1

2

10

3

6

13

_2 15 _7 J> 11 17 11 11

27 50

(see m/e 122) C H O , C ^ O N , 9

C

8

H

C

8 ° 2 ,

8

H

1 2

S

i a

i

>

C

H

5

1 2

S

2 »


CsHgOBr

C H 0 , Ph(Cl) (C=C)-, BrC H40CH -, C5H C1 , C H ON 8

9

2

2

8

2

7

2

2

n


138.

2

HOOCCHBr-j-R-j-H, HOPhCOO-j-R-j-H (rearrs.), C H P h C C l 4 : X , etc. 1 7 P . I . D . ions 2 4 1 Other unclassified _2 _1 _1 Total 4 6 9 3

138.9950 139.0314

2

C H C 1 0 CIPhCO 4 Y (Y= R, H, -OR) C H C 1 See C H C 1 7

4

8

8

Also:

7

6

C H , C H -thiophene-CH -, C H BrF, C H C0CC1 4X U

3

9

7

5

3

7

2 4 6

4 5 1 8

12 16 _5 33

8 13

1

1 5

9 19

4

2

2

8

1 2 1 _1 _2 _1 27 7 10

4 _4 44

2

2

5


2



58

m/e

140.0267

Formula


ProbabUit 7 2 3 A

5 Total

5

1

2

1

10

1

1

2

3

7


16 _1 7 19

7

3

6

9

6

10

33 1 51

Naphthyl-CH - f R, etc. PhOPhY (Y= H, X ) , PhPhOY (Y= H, R, -COR), 0=C(OPh) (rearrs. - loss of CO?)

7

5

1

13

3

10

13

3

5

3

11

2 _2 14

17 _2 32

7 _2 23

26 _6 69

C H N C 1 C l P h N H C H - f R, ClPhNUCOR)-CH 4-R (rearr.) 7

7

2

2

1

Also:

GyHgOCl [CHgOPhCl + HX, HOPh(Cl)CH4=R ] , C H N R , CHI 2

6

u

2


1

1

2

C H 0C1 (seeC H 0), CH I; PhS0 -, C H C l B r , ( C ^ J . A l 7

6

7

2

2

7

142.0185 142. 1595

142.9222 142.9920 143.0860

C

Naphthyl-CH f R f H (rearr.); PhOPh etc. (rearrs.) (see C H ) C H O C l S e e C H 0 (m/e 108) 3 CgHjjoN See C H N (m/e 100) 6 P . I . D . ions 7 Other unclassified Total 16

4

1 8 _3 10 15

C H C1 C F CuHj,

1 2 1

3 2

1

4 8 1 4

2

2

11

u

H

2

2

3


142.0078

1

1 0

2

1 4

2

U

7

7

7

6

3

2

4

5

Also:

1 4

C ^ C ^ + X, C H C1 -j-HX C F -f X , C F •{- OR See C H (m/e 129)

3

3

4

5

4

1 0

2

3

5

2

3 2

9

C H BrF , C H C1F , C H B r C l , CH OOC(CH ) -fR, naphthyl-Of 4 In Mass Spectral Correlations; McLafferty, F.; 2

2

2

1

8

4

3

3

2 4

7 4 9 22 3 45

3

8 1

2

3

3

2

6

1

2


Mass

Spectral

m/e

143.0860

144.

Data

m/e


Formula

C H u

59

140-146


n

4 2 7 2 _2 _1 _2 _2 _2 15 6 6 16 8

3


5 Total 15 _9 51

Naphthyl-0 + Y f H (rearr.) (Y= R, salicyl); C H - i n d o l e - C H -f, C H N O (amino alcohol), 8

2

18

Cl Ph+(N0 ) , 2

2

2

C3OCIF3,

6 1 1 2 1 11 2 1 2 7 6 18 _ _ _ _1 J . _2 8 2 3 10 8 31

PhC (CN) ( C H ) + P . I . D . ions Other unclassified Total 2

144.9612

C H C1

145.1017

C H

6

n

3

5

C l P h f Y (Y=-N0 , X, -COR) See C H , m/e 131

2

2

1 3

2

1 0

n

PhC(CN) ( C H ) 4 R + H (rearr.) C H C1 , CF Ph4x, C H C O O C H C H (OOCCH ) -

Also:

2

3

4

1 0

3

+ C - P h C O - j - Y (Y= OH, -CHC1R, etc.)

1 0

Also:

10 9

1

13

3 _4 11 16

13 11 56

1 1

5

2 1

1

4

1

7

3

2


C H O

8

7

5

3

3

146.0731

Relative Probability 1 ~I 5 4

1 6 _3 _4 15 14

3

3

C H . (145 or 147 larger), 0 N + P h C l + R = f H (rearr.) n

2

3

4

2

2


3

2

8 7 1 2 12 12

6 1 10

1 1

1

3 _1 3 5


7 25 5 42

60

m/e

146.9625 147.0461

147.0809 147.1173


Formula

Relative Probability S 3 %


C C1F C H Si 0 (CH ) SiOSi (CH ) - (often formed in inlet from other trimethylsilanes) (148, 66, 73 often large) C H O See C H 0 (m/e 133) C H See C H (m/e 133) 3

5

4

15

10

n

U

1 5

2

3

3

3

9

6

1

1

2

10

4 1 13

2 3

6 1

3

4 12 17

4

1

10

2 2 1 _1 _ J . J . 30 8 15 8

5 _3 61

2

9

1 0

5 Total

l 3

Also: Benzothiophene -CH + , CH COPhCO-, CBr* C1F, C F -CO+ 2

3


2

5

5

P.I.D. ions Other unclassified Total

148.0524

CgHgOa

PhCH=CHCOO + R + H (rearr.) (133 is base peak)

Also: C H N, C. H O, CHjjsCHPhCNO^-, C C 1 F l0

14

0

12

2

3

8

P.I.D. ions Other unclassified Total

149.0238

C Hj 0

149.0966

C H O

8

10

13

Also:

3

3 19 10 1 J. 4 24 13

Phthalates; terephthalates [ROf COPhCOO + R + H (rearr.)]; HOOCPhCO + Y (See C H 0, m/e 107) 7

5 43 1 4 8 10 59

11

7

C 9 H 9 O 2 (see m/e 135), Cl^PhSi (CH ) -, HaNPhN (CaHjCK,-, C H ON (see m/e 135), R + CH OSi(OC H ) 4OR(rearr0, FSO CF -, C H OBr 3

8

14 7

2

10

12

2

2

s

B

a

2

4

13

fl

P.I.D. Ions Other unclassified Total

21 18


16 _4 54

Mass

Spectral

,

Data

„

m/e

,


mlS. 22™** 150.0191 C H N0 , C H NO 7

4

8

Relative Probability 1 ~2 5 T 5 6 7 8

0 NPhCO + Y (seeC H 0); 0 NPhCH (CH ) + 9

3

8

147-152

2

a

7

8

2

3

1

Also: NCS-PhO-j-CH

3


2 P.I.D. ions Other unclassified 11 Total

12 17

11 _3 15

10 10

Subtotal, m/e 1-150 3217 3114 3167 1135 538 197 25 10

150.9329

C C1 F 2

8

3

8

4

151. 0758 C O , (HOjjPhC (CH ) -, CH0 (CH 0) PhC\-, CH O(HO)PhCO-, CH OOCPhO-, etc. 4 9

8

a

7

3

2

8 2

8

8

2

s

a

Also: IOC-, CH =CH(CH )PhCl + Cl, monoterpenones, C H 2

12

1 3

7

P.I.D. ions Other unclassified

C H

2

Ph * Y [ Y= X , (OH) , 0=C + , R, -OR], PhCHRPh

8

1

8

12

152.0626

3

2

3

3 3

1

3

4

2

1

2 1

2

2

Also: CH 0-C H 0 (see C H O ), O N(HO) PhCHj,-, CH =CHCON-(cyclohexyl)-, Cl-benzoxazolyl 3

7

7

e

B

5

2

a

a

2

2

P.I.D. ions 3 5 8 2 Other unclassified 2 In Mass Spectral Correlations; McLafferty, F.; 2 Advances in Chemistry; American Chemical Society: Washington, DC, 1963.


62

me

153.0471 153.0704

Relative Probability 1 "1 3 4


Formula

C ^ C l Cl2 9

5 Total

See C H C 1 PhPh + Y ,(Y= - N 0 , X , R); (naphthyl-C=C) + R + H (rearr.) 7

H

6

2

2

Also:

B r C H C O O - f R + H (rearr.), TiCl , (CHsOkPhOf, CH OPhCOO + R + H , thiophene-COCH CO + 2

4

?

3

3

2

2

16 4



154.

HCONHPhCl-, P h S i C l , (rearr.), CF CON(C H ) CH -, C H O C l (seeC H OCl) P . I . D . ions 2

2

3

2

8

155.

5

2

7

7

3 1

5

C H O C l (see C H 0 ) , B r P h -j- Y (see P h f Y), C H 0 C 1 ( s e e C H 0 ) , (P.H.O), POO + C H + H , H + R + O- (C H O-) POO+R=f=H , etc. (rearrs.), C H B r C l , Q F , C H B r F , PhPO(OCH )-, naphthyl-CO-, C H P h S 0 - , H C O O C C H C O - , (pyridyl) -, C H -naphthyl-CH -, C u H f CH NH 11 P . I . D . ions 8

8

7

9 20

7

7

4

2

7

2

4

3

5

2

2

9

2

8 1

3

5

3

2

3

2

3

3

9

4

2

2

2

3

2

2 3

156.

2

2

2

C H N ( C H ) C H , - , etc., C H -quinoline-C H -, etc., Br-pyridyl-j-X, (HgC ) NCO-j-R P . I . D . ions Other unclassified 8

1 7

34 15

11 4

3

3

2

4

2

1 7

1 1 3 7 3


3

4 2

6 24 2

Mass

Spectral

m/e

Data

m/e

63

753-767


Formula

1


5 Total

156.9244 C ^ B r ^ C l 156.9465 CaH^BrFa H -f ROOCCH 4 C (COOC H ) C H C 0 40R=|=H ( r e a r r . ) ? , ( C H ) S i 4 S i R , 1-Ph-(CH ) pyrazole 4 X

Also:

2

4

9

2

7

3

3

3

:

3


P . I . D . ions

158.0969 158.1095

C

C

iiH 1 2

H

1 2

5

2

2

1 2

H

1 5

3

3

, C HgBr-, CHFI6

C B r F , CH 0-indole-CH 2

3

3

11

2

4 4 2

2

3 1

11 8

4, 2 3


C

12

H

See C

1 7

Also:

1 0

H

1 3

1 3

3

2

3

5

1 1

3 20 3

12

{m/e 133)

C H 0 , CH -benzothiopheneC H + , BrC H 1 0 4 , C H C O N (Ph) 4 R 4 H (rearr.) 1 1

3 17 6

10

C14Cl2Ph04H

161.1329

23

8

1 3 3


160.

4

2

2

C

8

4

C l P h C H 4, P h C C l 4 X ; Cl PhC (CH )

2

Also:

3

3

2

2

7

2

(CH •indole-CH h) -cyclohexyl 4 OR H4 (R= - C H O H , H) P . I . D . ions Other unclassified

N

1 4

158.9768 C H C 1

1

2



64

m/e

Formula

161.1329 C H 1 2

161.9639

4

C l P h O + Y + H (rearr.) (Y=R, -COR, C H S 0 - )

2

Also:

4

9

1 5

0

u

2

9

7

1 2

1 9

4

2

4

3

2

4

5

1 0

3

3 6

3

1

20 10

6

9

13 1

16

1

11 7 1 2

3 41 3

7

4

1

12

5

2

3

10

3

1 3

C H - C H 4 H 0 H , C Hg (CH O) P h O + R f H (rearr.), OHC (CH 0) PhO+R •f-H (rearr.), H+fluorenef CN P . I . D . ions Other unclassified u

15 1

3


6

2

7

C H , C B r " C l , (C H 0) Si-, C H C1F , C 0C1F , C H ON 4

164.

4 Total

1

3

C CI F C H d, C. H O , C H 0 (see m/e 149) Also:

3

2


u

2

9

2

PhN(C H )-CH 4-, PhN (COCH ) C H C H + 3

162.9329 163.1122

1

2

3


Probability

(Cont'd.) P . I . D . ions Other unclassified

1 7

C H OCl f l


3

4

3

4

1 3

4 4 1 3

11 4

13 1 8

s

3

165.0704

C

1 3

H

2 7 3

19

1 2 5 9 4 39 2 1 6

1

Y-PhCHZPh-Y , ar-Ph-Z-CH benzofurans, Y P h - P h ( Y ) - C H (Y=Y=X, - O R X , -OH; if Y= R, 167, 166, or 168 larger) (Z= R, X)

9

3

,

3

165.0915 C H O CgHgOg 1 0

l s

4

15

2

See m/e 151


5 24

Mass

Spectral

m/e

165.0915

Data

m/e

Formula

162-168

65


PrôbabUilty 2 3 4

C H O (Cont'd.) Also: C H B r C O O C H C H +, ClPhCH=CHCO-j-, Cl-benzo furan-CH -j-, ( H C 0 ) O P C H + , C C1 2 1 0

1 3

2

2

3

2

5

5

2

2

2

4

3



166.0782

C H 1 3

5 Total

(Ph C)YY' R)

1 0

1

2

5

3

12

6

7

3 2

17 2

2

2

2

7

(Y= X , OH, Ph,

2

1

37

Also:

C C1 C1 , (C H PhOCl)fX , carbazole+, 0 N (HO) P h C O + , P h ( C 0 0 4-R-|-H) (rearr.), CIPhN ( C H ) + C O R 2

8

3

5

2

2

2

3

5


166.9034 167.0860

C C1 F C H 2

3

1 3

U

Also:

2

2

2

4

1

2

11

5 1

6

3

7 4 1 3

25 5

1 1 2

P h C H -j- R, PhPhCH 4 R, acenaphthenes

7

5

CIPhN (CH CH=CH ) -j-COR-f H (rearr.), C H CI, CI (HO) P h C r f i c H , H 4-R f OOCPhCOO-f R f H (rearr.), C H C 1 C 1

4

1 2

2 2

2

2

6

2

2

12

2

3

4

3

7

2

3,?

2

S


168.

(Ph O) =j=Y (Y=C1 , CO, C O R + X , etc.), (Ph N) + Y (Y= R, -COR). CgHgOCl (see C H O C l ) , 0 N P h f NO-j-0 (rearr.), C H 0 (seeC H O ) 4 P . I . D . ions 8 Other unclassified z

2

9

3

1 2 5 3

8 10

5 6

4 6 2

15 27 2

2

2

7

2

B

8

7

e

a

8

4

2 7



66

m/e

168.9653 169.0420 169.0653

C H B r See C H C H OClSee C H 0 C H 0 PhPh04; PhOPhf-Y, H O P h 4 Y ( Y = X , -OPh, etc.) 7

6

7

7

ff

10

7

7

1 2

9

2

3

6

2

19

5

3

3

7

2

3

3

4

8

2

9

12

X0

1 0

n

5

2

2

15

2

2

8

16 3

3 1

P h P h O - j - Y - f H (Y=R, -COR) 10 (rearr.) (H C ) N C H f , B r P h N H -j-COR, (pyridyl) N - , C H . (CI) P h O f R O f H (rearr.) P . I . D . ions Other unclassified

C H O

C H.C1

20

3


170.9768

11 6

2

3

1 2

7

P h N + C O R 4 H (rearr.), CIPhSi ( C H ) - , naphthyl-Cs-, C l C H C O O C H (CH )-, H C O O C C H C O - , Cl-terpenols, C F ; C1CH C0N (Ph) f R + H (rearr.), etc. (see C H O N ) , C H25, B r (HO) P h ^ X 5 2

170.0731

4 4

5 Total

2

Also:




Formula

3

6 28 2

Cl PhC *HX , C l P h (C=C)-f X PI - f'Y"- j -' H P h - "P h - O (Y=-R-OH, - C O C H ; R) (rearr.) 2

2

2

2

171.0809

C „ H O0 tu 1

1 2

2

3

Also:

RO 4 C O C H C O O 4 R 4 (rearr.), F P h P h 4 H , C C 1 F , CH OPhS0 + X H

7

14

5

3

4

2


171.9524

C H O B r BrPhO 4 Y 4 H (rearr.) (Y= R; -COCH ) 5 C H C 1 C l P h C H 4=X 1 P . I . D . ions 7 unclassified InOther Mass Spectral Correlations; McLafferty, F.; 6

5

8

6

3

171.9846

2

2

2

3

23 5

14 1

2

3 1 3

1 1 1 2 4 3


7

7 4 24 4

M a s s Spectral

m/e

172.9924

Data

m/e

67

169-776



Formula

C^KyC^

5 Total

C H (Cl ) P h C H - , Cl PhCH (CH )-; Cl PhCH CH |X 3

2

2

2

3

2

2

10

2

81

Also:

Cl PhCO-, C H , CHBrBr C H C O O C H C H (OCOC H )2

1 3

2

5

1 7

2

2

5

10 10



174.

C H = C H - C H N (COCH ) Ph + C l , H B r B r C - | - C O O C H -f H (rearr.) ? P . I . D . ions Other unclassified 2

2

3

81

2

174.9717 C H O C l ?

5

4

7 1

Cl PhCHOHf, Cl (HO)PhCH f, Cl (HO)(CH )Ph+X ClPhOCH -fCOOR, etc. 6 See C H (m/e 133), also perhydropyrene 6 2

2

2

2

1 0

Also:

2

2

1 2

2

H O l e

2

4

12

1 3

12

1 3

3

2

2

2

4

1

1 5


176.1201

2 30 6

2

C C 1 F , PhSiCl -, H C=CClCH OCOC H CO-, C H 0 4

3 1

3

2

175.1486

1 1 11 1

Cyclohexyl-PhO f R f H (rearr.), etc. P . I . D . ions Other unclassified

5

15

18 4

2 2 10 10 1 1

4 29 3


ADVANCES

68

m/e

177.1279

Formula


C H 0 i a

2

6

1

4

1 1 3


2

3 2

Dihydroethanoanthracene, etc.; P h C ^ X ; 179 larger

2

1 2

4

9

9

s

CjjHaBr C l , C H O C O P h C O - , CgHÔBr, C F I 2

2


1 0

2

2

4

11

8

4

C3CI3CI ,

Also:

HOPhN(C Hg JCHj, PhCHfCHaMCÔHjCIij-f-

6 2

9 4 1

13 7

2

7

3 7

4

2


178.9034 179.0860

5 Total

2

2

1 4

4

81

Also:

C H

3

3

4

178.0782

SERIES

Probability 1

C H (HO) PhCH (CH ) 4-, C H (CH O) P h C H 4 , etc. (see m/e 107)

1 7

I N CHEMISTRY

C C1 F C H 3

3

1 4

U

2

P h C H + Y (Y= X , H ; H X J , (CH ) PhOPO (OPhCH ) OR (rearr.), etc. 2

2

7 2

1

22 3

5

2

1

8

1 3

3

1

8

3

3

3

9

3

3

3

C B r F , CH OCOC H Br f , C H B r s i C l F , C HC1 C1 , C H 0 , Cl Phf X 2

10 1

4

2

3

Also:

4

2

4

3

3

5

37

2

u

2

1 5

2

3

3

3


180.0660 180.0938

2 1

C H N O 0 N (HO) PhC ( C H ) C H (CH PhCH -) , (H C Ph-) , 9

1 4

10

1 2

8

2

3

3

2

2

2

5

2

3

2

1

2

15 2

2

2

(CH Ph-) CHR,(PhCH)24x P . I . D . ions Other unclassified

7

2

2

6

5

5

3 1


5

2 19 1 1 2

Mass

Spectral

m/e

Data

m/e

Formula

177-184

69

Structural Significance 1

180.9888

C F 4

PhPhCH (CH ) 4 > CI ( C H ) PhCH (CH ) - j - , PhPhNOfO 3

3

7

3



Ph NCH - h (0 N) PhNH-fCOR, P hhCH C H PhNH-fPhNHf P . I . D . ions Other unclassified 2

2

2

2

1 1

1 1

8

2

2 11 1

1

2 1

C H 4 B r O BrPhCO-{4 C H B r See C H 3 C H O PhOPhCH 4-, C H O P h P h - | - X , PhCH PhO + , PhPhOCH 4-, 7

8

8

1 3

8

9

n

2

14 4

1 2 4 4

5 22 2

1 1 1 4 1 2

7 10

3

2

etc.

184.

3 3

3

2

Also:

4

2

22

182.9446 182.9810 183.0809

5 Total

7

Also:

182.


5

Ph SiH-, C F S S C F P . I . D . ions Other unclassified 2

3

2

1 4 1

PhCH PhOf R f H (rearr.),C H^N (see m/e 170), (0 N) PhO+R+H (rearr.), H N P h B r f X , O f O N P h C O C H f Br P . I . D . ions Other unclassified 2

2

3

13

1

1 6

2 11 3

2 6

7 30 1

1 1

1 2

2

8

2

2

3 4

2 10

10 1



70

m/e

185.

Formula

Relative Probabilil 1 5"


SERIES

5 Total

3 7

C H O O C C H CO 4- OR, C C 1 C 1 F , X 4- ClPhOCH COO f R + H,(rearr.) C C1F , CaHBrBr , B r (HO) (CH ) Ph-j-X 2 P . I . D . ions 1 Other unclassified 4

g

4

fl

2

3

2

81

3

6


3

186.

2 7 3

P h O P h O f R-j-H (rearr.), C H O O C C H C O f OR f H (rearr. ) , C H B r B r =j=Br ClPhPh=j=Cl P . I . D . ions 4

9

4

8 14 5

3 3

8

8 1

2

2

2

2

187.

C H 1 4

1 9

( s e e C H ), C l P h C ( C H ) - , C H BrBr* P . I . D . ions Other unclassified 1 0

2

188.

2

3

4 1 3

In 10 highest peaks, only ion classified was ( n - C . H ^ B O C H g 4 + (rearr.) (10th highest in spectrum) P . I . D . ions Other unclassified

C^Ha Also:

See C H 1 0

1 3

4 22

2

3

R

189.1642

5

8 11 6

H

21 1

(m/e 133)

CglLjOClj, (see C H 0 C 1 ) , C H 0 , CH =CHCH OCOPhCO7

1 3

1 7

5

2

2

2



11 3

Mass

Spectral

m/e 190.

191.0860

Data

m/e

185-194

_ . Formula


Relative Probability 1 2 3 4 5 6 7

CI (OaN) Ph + C l , 2-cyanof luorene {• H P . I . D . ions Other unclassified

C H , C ^ H j g : Anthracene-CH -f, phenanthrene-CH - j - ; tetradecahydroanthracene-f etc. C H 0 See m/e 177 1 5

2 2

1 7

5

7 1

6 3

3 3

3

1

8

2

2

2

U


2

2

191.1435

1 3

1 9

Also:

C C C C C

4

C1 F , C H C10SiCl -, B r F , C B r B r F, HC1 C1 , C g H ^ r C l , C 1 F S , B r CIPh-f-X, H F I , C H OCOPhCO-|3

2

3

6

2

8 1

3

4

37

4

8 1

3

2

m

4

4

2

2

2

3

7

P . I . D . ions

192.

CH OPhN (C H ) C H - j - , Cl PhCC14=Cl P . I . D . ions Other unclassified 3

4

g

2

2

193.

C H 1 5

1 3

1 5

2

(see m/e 179), ( C l a P h q -) (see m/e 159), (C H 0 ) S i O C H + , C H 0 (see m/e 151), S b C l , C H OCOC H Bri P . I . D . ions Other unclassified 2

5

3

2

1 2

1 7

2 1

1 6 3

1 7

1

4 1

2

2

2

194.

5

3

5

7

C C1 F , C H OCOPhCOOf R f H (rearr.), C l P h (OH) 4=HC1 2 4

2

4

2

3 2 6 3 1

2

1 1 2

3 1

1

1

5

3


1

72

/ m/e w

194.

195.

A D V A N C E S I N CHEMISTRY SERIES rv^„i„


Formula

C C1 F (Cont'd.) P.I.D. ions Other unclassified 4

2

C HIB 1 5

4

1 3 4 5 4 3 3 23 1 1 1 3

(see C i H u ) , Cl PhO-, Ci H O [PhCOPh(CH )-, etc.], (CHj^hOPOfOPhCiyOR, C H Cl(see C H C1), CF PhCF -, PhBrC H 7 4 2 P.I.D. ions 15 3 Other unclassified 4 11 3

3

4

u

3

12

16

3


Relative Probability 1 2 5 4 S 6 7 Total

7

6

2

3

3

195.9249 CeHsOCls See C H OCl (m/e 162) 17 fl

4

a

6

Also: PhCH N (Ph) CH -, CgHgBr 0seeC Hj,(O N) Ph HCH a

1

1 2 21 1 11 1 7

25

2

9

2

2

1 1 3

a

P.I.D. ions Other unclassified

197.

1

2 3 1

7 3 3 6 1 1 2

5 1

20 4

3 4 11 2

22 8 2

9

3 49 1

81

C H Br(see CgH^CaBr C1F , HOPhCOPh-, HO (O N) PhCH -, q H 0(see C HuO), C C1F , H C (CI) PhOCH -, BrCOCaHgBr -, Ph Si(CH )-, C H 8 P.I.D. ions Other unclassified 9

10

3

a

a

4

4

6

fl

a

l3

18

4

a

81

2

3

198.

1B

17

7 15

(H C ) NCH -, HO (O N) PhCH -, (CH ) NCONHPhCl + X 1 1 1 P.I.D. ions 2 26 12 Other unclassified 1 18

fl

a

a

a

a

a

8 a


Mass

Spectral

*»U m/e 199.

Data

m/e

195-203


IT™™,!*

Formula

Relative Probability 1 2 3 4 5 6 7

81

C H B r B r , Br (HO PhCO -j- R, Cl2-benzafuran-CH C HC1 F P.I.D. ions Other unclassified

2 2 1 4 5 3 3 2

ClPhC(Ph)+HCl (?) RCO0 4- 3H4Br +H P.I.D. ions Other unclassified

1 1 4 3 13 9 6 1 2 2

3

3

2

3

200.

3

3


C

2

201.

8 1

81

C H BrBr , C HOBrBr , ClPhCH Ph4-X, C C1 F , CjjCl^Cl , (C H ) (CH ) Si H-, C H . P.I.D. ions Other unclassified 3

B

2

a

3

2

5

37

4

202.

9

a

3

a

2

4 2 1 1 2 1 1 3 3 3 2 2 1 1 1 1

M

Hg, Hgf(CF ) , (CIPhOPh) ^ C l , Cl (CH 0) Ph-6HCH7fS H 2 1 1 1 P.I.D. ions 5 4 3 4 3

2

2

2

3

4

203.0030 C H9 0C1 See C H 0C1 203.0263 C H 0C1 CIPhOPhfX, CIPhPh (OH) +X, CI (PhPh) O-f COR 203.1799 C H See^C H^jm/e 133) 9

2

12

7

B

8

2

4 1

1

1

1

1 1 1

2

11

8

1 5

a 3

10

,

2 3

fcpST 2

(?)

'P.I.D. ions Other unclassified

2 1

5 2 3

2 2 2


74

/ m/e 204.


, Formula

Structural ance

Relative Probability 1 2 3 4 s / 7 Total

S i g n i f i C

Phenanthrene = ( C H ) 4= ( C H C H ) , C H Br Cl P . I . D . ions 5 Other unclassified 2

2

2

2

8 1

4

205.

5

2

1 1 6 5

4 2 1

2 1 27 1 1 3

4

C ^ H ^ O f s e e m/e 177), sesquiterpenones, C H B r C l , C H OCOPhCO+, C F , C H O C H B r f X , BrPhCF -f, 8 1

7

4

2


5

9

6

5

6

7

9

2

Br-naphthyl4x,

7 1 1


206.

C H ( C H 0 ) P h O + R - j - H (rearr.), C PhCl 4=Cl P . I . D . ions Other unclassified 4

9

3

1 1

3 3

3

3

1 13

3

3

14 4

5

2

207.

1

3

2

7

1 1 2 9 6 2 1 1

3

4 27 2

C H O , C H O (see m/e 151), C l P h C \ (see m/e 173), methylsiloxanes, C B r B r CI, C H 8 P . I . D . ions 1 Other unclassified 1

4 4 1

1 1

16 14 3

Pb

3

7

10

1

1

9 2

8 1

1 3

1 9

z

1 2

3

1 5

s

2

8 1

1 6

207.9766

Also:

1 5

R Pb 4

OCNPhCH Ph f , PhPhOC H ^=C HPh

1 3

2 6

2

3

3

3


7

4


28 3

Mass

Spectral

, mje

209.

Data

m/e

204-212

„ , Formula

75


Relative Probability 1 2 3 4 5 6 7 Total

C H C 1 (see C.H.C1), C H C 1 0 , C C1 C1 *F, ^ H ^ O , C H (PhCOPh) C H -f- (see m/e 195), C H C 1 0 (see C H 0), C Br8iClF , B i ^ R , H C OOCPhCOO-j-R-j-H (rearr.) 7 P . I . D . ions Other unclassified 1 3

1 8

12

14

3

4

3

2

7

7

7


211.1122

3

3

3

210.

4

3

7

3

0 NPhCH=CClC0 4P . I . D . ions Other unclassified

4 5

3 4

6

8

1 4 1

7

1

2

C H O 1 5

HOPhPhC ( C H ) + , PhOPhC ( C H ) -f, etc.

l s

3

3

Also:

1 1 3 2 1

3 1

6

2

5

18 14 3

1 31 1

2

2

8

HO ( 0 N) PhCH (CH ) f , C H B r F , ( H C 0)2 OPO-j-R-|-H (rearr.), C HBr Cl , C HC1 F , PhPhSi(CH ) -j-, 2

2

3

3

5

9

4

2 8 1

2

3

3

4

3

3

2

H„ C -naphthyl-CH 4. 5

2

P . I . D . ions

212.

Hg C ( B r ) P h O f C O R - f H (rearr.), PhOPhC H -fR-!-H (rearr.) P . I . D . ions Other unclassified

8

6

1

5

2 2 1

1 4 1

5

1 4

1

4

2

15 22

3

3

6

7

8

1 6

3


4 30 2


76

me 213.

Relative Probability 2 S 4 S16 H J 9 10 Total


Formula

C C1 F! 4

2

HO" . H C OOCC H CO-f, etc. P . I . D . ions Other unclassified Publication Date: January 1, 1963 | doi: 10.1021/ba-1963-0040.ch001

1 3

214.

6

4

8

P . I . D . ions

3 10 5 3 2 3 4

30

(Y=OH, -OCOR), corresp. olefin

12

3 2

12

1

1

4

2 2 2 2

1

9

2 8 1

12

23 1

C H BrBr , (H C ) Cl PhCH + , Cl Cl Phf, CH benzanthracene 4

2

2 8 1

2

3

2

3

P . I . D . ions


216.

l e

3 1

7

5

C H,

20 16 1

8 1

Also:

217.1955

SERIES

l

2

7 3

(?)

2 2 1

1


6

Mass

Spectral

yyj/p m/e 217.1955

Data

m/e

„i„ Formula

273-227

77


Relative Probability 1 S 3 4 S 6 7 8 9 10 Total

C ^ H J S (Cont'd.) Also: Other C ^ H ^ (see C H ) , CILO(Cl ) PhC(CH,) +, C l ( C H . O ) PhPh+Cl, CI^Hgf, (PhO) Pf, 1 0

1 3

2

a

2

C C1 F 3

3

4 11

4


P . I . D . ions

2 12

218.

HOPhl+Ij,, ( H C ) N C H P h + P . I . D . Ions

219.

C BrBr Cl, C F , ClfCl PhOCH COOfR+H (rearr.), B r P h S O - ; CeH^r^CUsee C H ) P . I . D . ions

9

4

1

7

2 1

8

1 1 5 3 7 3 4 1 2

2

2 25

8 1

2

4

9

2

2

z

8

220.

ClPhOPh04R+H (rearr.), (CH ) N C O P h ( C H ) + C l ; H C (C H )-cyclohexyl=l=HOH 11 1 P . I . D . ions 3 3 4 3 2 5 2 1 1 Other unclassified 1 1 1 3

9

221.

2 1 1 1 2 2 1 1 3 2 1 2 1

9

4

4

6

9

n

C H 0 Si , Ph -C H f R , Cl Ph f,(H COOC) Phco+, c 0 ^ , 0 , ( 0 1 , 0 ) , PhOf, Cl (H C )PhCH 4, PhCOCH=C (Ph) OIL f , O C f NPhCH(-NCO)+(?), Cl -2,3-dihydrobenzofuryl+; C l P h O C H C O O 4.R+H,C H BrBr Cl 3 3 4 3 1 P . I . D . ions 1 1 1 5 5 Other unclassified 2 11 6

1 7

3

3

2

9 11

2

5

2

3 24 3

7

3

2

4

3

5

2

2

3

2

2

2 8 1

2

1 1 1 1 18 1 1 2 1 18 1 1 6


78


y

m/e

_ , Formula


222.

C BrF ; C C1 F P . I . D . ions Other unclassified

1 1 4 2 7 3 3 2 6 5 4 1 2

223.0001

CH Pb

3 5 1

4

5

5

3

3

CHgPb^RR'R"

3

Also:

C H Ph CH(CH )i-, Cl(H C ) PhCH(CH )f, etc., H C ( O N ) P h f , H C OOCPhCOO-j-R4=H (rearr.), C C 1 F S , H*RfPh (C H )CH(CH )f (rearr.), CI P h O C H (CH^+COOR; H C -cyclohexyl-f3 3

7

2

7


Relative Probability 1 2 3 4 5 6 U 910 Total

9

3

3

2

9

9

2 37 2

3

4

z

2

4

2

4

2

4

3

2

7

3

3

21


224.

H +

4 1 1 1

10

2 2 4 1 1 1

H^C^HUCBJCH+R,

H C OPhPhfHCl,(C F ) P . I . D . ions 3 6 Other unclassified 9

225.

4

6

8

4

3

11 2 5 17 1 2

1 1 2 4 6 2 1 3 1 26 11 2

CI ( H C ) (HO)PhC(CH ) +, etc. C C 1 C 1 , C Br Cl F , H C naphthyl-CH(CH )f, HO(0 N) PhC(CH ) f, Br(H C )PhCH(CH )f, PhOOCPhCO f OR, PhOPhC H f ;C C1 F , H 3 1 ^ 1 5 ( H C ) CH-j-R 6 12 1 P . I . D . ions 2 1 Other unclassified 1 1 1 1 9

1

2

3 7

4

4

s !

3

2

2

U

B

3

2

7

2

3

3

B

3

4

8

n

5

2

5

5

2

1 2 13 2 1 4 12 1 1 6


Mass

, m/e 226.

Spectral

Data

m/e

_ , Formula

222-230

79


Relative Probability 1 3 8 4 5 6 7 8 9 10 Total

( H C ) N C H f , etc., C H + (H)R, P h P h O C H (OH) 4 H O H ; 1 3 3 2 1 3 1 P . I . D . ions 3 6 2 2 4 4 2 3 1 2 Other unclassified 1 1 5

7

2

2

1 8

1 0

3

4


?

227.

C H f . R , H C (HO)PhBr4-X P . I . D . ions Other unclassified

228.

C H = t (H) R etc.; C H B r B r 4=HBr P . I . D . ions

1 8

u

18

9

4

1 11 2 9 3 1 2 1 2 4 2 2 1 1

1 6 26 2

2 11 4 3 3 2 4 1 2 1 1 1

4 22

12

8 1

5

229.

14 29 1 2

C1 C1 3

8

3 7

(H C) P h f X , etc., C H B r B r -j-X, C HBr ClF , B r H C = C B r C (OH)(CH ) 4"?) CjiHigSig, C^PhOf C H C l f C l (rearr.), C H C 1 C 1 F , C C l s F , P h P h P h f R; F CCC1FC (CF )(OCH )4- OR 9 P . I . D . ions 13 Other unclassified 3

8 1

5

9

8 1

3

4

81

3

3 7

2

3 7

4

4

3

230.

3

3

H C C O N (Ph) C 4 - X P . I . D . ions Other unclassified 1 3

6

2

4

3

3

1 24 1

2 2 2 1 1 1 2 12 11 2 1

2 2 1 1 3 1


20 11 1

1 16 1


80

_ , jormuia

231.



(HgCjaPhC ( C H ) f , etc., ClH C OPh (Cl)C(CH ) f, H^CioCHPhf, perhydrobenzanthracene -j-R, ClH C OOCC H C O O C H - j - X , H C Hg-f-R, C F ;CH ICHPhfOH, Cl Cl (HO)Ph f X 2 1 3 2 4 1 2 1 1 P . I . D . ions 1 4 2 3 2 1 Other unclassified 1 1 1 3

4

4

3

3

2

3

5

2

2

4

4

9

2

5

2

2

37


3

232.

233.

P . I . D . ions

C KO le

6 1 1 2 1 2 2 1

[ C H 2 (see m/e 215) + H 0 ] , Cl -benzofuran-CH 4 > (C H C10) P0C H +C1, BrPhPhfX; C C1F , (PhO) POfOPh P . I . D . ions Other unclassified

x

16

17 13 3

3

19

2 1 1 3 1 2 1 4

7 14 1

3

2

3

2

2

4

7

2

2

6

4

2

234.

B r B r a i Ph4=Br P . I . D . ions Other unclassified

235.

(ClPh) CHJ-Y (Y= X , R), C C1 C1 F , Br Ph-fY*. C H C10SiCl -

2

1 2

2 1 1

1 1 4 4 1 4 3 4 11

1 21 2

2

3 7

3

3

3

3

6

2

2

( C H CH CHo) CHfR; (C H ) Cl Ph+Cl P . I . D . ions Other unclassified 6

n

2

5

2

2

3

2

5 1 2 2 1 1 3 4 2 3 1 3 1 1 1


1 20 112 1

M a s s Spectral

Data

Formula

236.

237-240

81


Relative Probability 1 2 3 4 B 6 1 S 9 10 Total

m/e

HO(0 N)Ph(C H )f. PhOPhCl fCl CH =CHSPh(Cl )+Cl . CMCaHjPhO+COR+H (rearr.); Hg C ^12 ^ 2 3 4 = (H) R, B r (H C) (HO) Ph4=Br , (C F ) P . I . D . ions Other unclassified 2

7

14

2

2 >

2

3

2

5

2

3


7

237.

2

H C Pb + R. ,, H C -thiophene - * C ( C H ) + , C 1 ( H C ) (CH )P h C H ( C H ) - f , etc., P h O P h C l + CI P . I . D . ions Other unclassified 2

5

7 26 5

8

33

1 7

8

3

7

3

2

2

3

3

2

238.

239.

(CH ) Pb=j=R P . I . D . ions Other unclassified 3

2

1 1 15 3 2 2 1 2 3 1 2 1 3 1 3 2 2 2 4 21 14 6 1

2

7 5 5 4

Br"Cl PhCH -f, H C naphthyl-C H 4-, PhSiH PhSi ( C H ) f , C H „ (m/e 241 larger), K^C -f COOR, C H Br"Cl f; PhOPhC H + , C^H^COf 1 2 P . I . D . ions 2 Other unclassified 1 3

2

n

3

2 2 5 1 1 3 4 35 1 2

5

6

2

3

2

1 9

17

4

5

3

5

240.

10

1 1 1 13 1 1 2 2 11 2

3 7

C C1 C1 F , C H (m/e 239 larger); Cl PhOCH CH 0+ R + H (rearr.) P . I . D . ions B

3

2

3

1 9

1 2

2

2

2 1 1 1 2 1 5 2 5 7 1 1 3 1


7 26


82

, F

241.

o

r

m

u

l


a

Relative Probability 1 2 3 4 5 6 7 ft 9 10 Total

BrBr^-cyclohexyl-j-, C B r F , C C1 F , ClC H OC H OPhC(CH ) 4-, C H (benzophenanthrene-CH -{-, etc.); B r * C l ( H O ) P h f X , HgC.OOCCeH^COf, C HC1 C137F , CHBr=CBrC (OH)(C H )-f 4 4 1 1 1 2 P . I . D . ions 3 1 2 2 2 4

5

3

2

4

3

6

4

2

4

2

1 9

1 3

2

2

5

3


2

242.

2

5

3 ,

Ph=(C Cl Cl 0+Cl , 2

3

etc

2

1

P . I . D . ions

243.

4

5

2

3

3 16 12

2 2 1 3 2 3 2 3 6 4 1

C l ( H C ) P h C H f , etc., H C l C P h C C l C l f , etc., P h C f , Cl PhS0 -j-; C F 4 1 1 1 P . I . D . ions 3 2 1 1 Other unclassified 1 2 2

2

6 28

2

3 7

2

3

6

3

2

9

2 2 1 12 7 1 4

244.

P h N P h 4 - H (245 base) P . I . D . ions Other unclassified

1 3 3 2 4 3 2 1 1 1

245.

Tetrahydronaphthacene-CH -f, perhydr onaphthacene + R, ( C F C H 0 ) P O + OR;H 0 O(H C ) Ph-f CI 2 1 P . I . D . ions 1 1 4 2 4 1 1 2 Other unclassified 1

2

1 19 1 2

2

3

5

2

3

2

9

4

2


1

4 16 1

Mass

, m/e

Spectral

Data

m/e

„ , Formula


246.

247.

83

247-250

Relative Probability 1 2 S 4 5 6 1 6 9 10 Total


Cl CI

3 7

3

(HO) PhO f C H , C C1F , C C1 C1 F P . I . D . ions Other unclassified

4 4 2 1 4 2 4 3 2

3

3 7


5

248.

8

4

3

1

3

2

4

3

2

5

1 1 1 4 2 2 1

4 12 2

1 2 1 4

2 17

3

2

2

2

2

2

249.

2 2 1

(H C ) - c y c l o - S i 0 4= (C H ) (?), P h C l C + C1 P . I . D . ions 5

1 1 1 3 3

2

C l ( H C ) P h C H - f , etc., BrBr PhCH f, etc., (C H C10) SiCl + , C ^ C l ^ P h - f , other, C e C l . C l , C HC1 C1 , (ClH C 0) POOC H + C1, C C 1 F ; (OCNPh) CH+ 4 12 6 13 P . I . D . ions 1 1 2 3

24 2

5

2

2

2

8 1

2

3

6

2

3 7

3 7

3

4

2

5

2

7

2

2

4

5

2

250.

8 1

BrBr (H N)Ph+Br P . I . D . ions Other unclassified

11 19 1 1 1 1 8

1

2

53

53 2

1 2 2


1 21 1 3


84

251.

8

CBr Br i, 2

CI ( H C ) P h C H (CH ){-, PhPhC ( C H ) C H j C (CH ) f, C ^ C P ' F , ; B r B r (HO) P h - f B r , C H C H C H (C H )-jP . I . D . ions Other unclassified 9

4

2

3

a

3

6


Relative Probabilil 1 a 3 4 5 6 7 8 9 10 Total


Formula

252.

253.

a

2 8 1

n

2

1 0

a


H

(CH ) Pb, 3

J A T B J *

,

3

H

3

3

3

3 2 1

3

1 4

4

4

3

2

2 1

1

2

7 25 1

27 2

(?).

(Y= - O H , -COOR), corresp. olefins (^19^25)' 8 1

C l P h C H B r -j-Br P . I . D . ions Other unclassified 2

254.

2

3

1 - f CHI, I 4 - C H (rearrs.) P . I . D . ions Other unclassified 2

2

2

6

3

13 7

1

2

1 1 4 3 5 2 1 1


2 16 3

Mass

/ m/e

255.

Spectral

Data

m/e

251-260

n «^ i Formula


Relative Probability 1 2 3 4 5 6 1 ft %10

81

CgHBrBr C l , C H ( C H less one Y g p . ) , C F ; CHg-benzanthracene-CH 4P . I . D . ions 2

1 9

7

1 9

2 7

2 5

9

2


256.

C C1 F 6

2

C

1 9

H

2 9

3

1 2 2

3 1 1 3

(C less 2 Y gps.), C 1 C 1 M H C ) PhCH -}- 4 1 P . I . D . ions 4 Other unclassified 1

1 1

1 2 1

19

3

3

258.

259.

2 1

6


257.

1

5

2

1 1 2

2


4 3

1

1 1 1 1 3 3 1 1

3 7

C H Cl5Cl -j-Cl, C C1 C1 F , ^HgBr C1 F , ( C H ) P h C H (CnHa) + , etc., C H C 1 0 P h ( C l ) C (CH ) + 3 1 1 1 P . I . D . ions 3 Other unclassified 1 6

5

3 7

5

3

3

8 1

2

3

4

3

260.

C C1 C1 4

S

2

8

2

3 7

5

P . I . D . ions

1 11

1 2 2 1 4 2 1 2



86

, m/e

261.


262.

263.

. Formula



C C1 F S, C HC1 F P . I . D . ions Other unclassified 4

3

4

5

3

SERIES

1 1 13 3

5

1 1 2

1 3 13 1

11 1

8 1

H -f (BrBr ) PhCO f OH, (C F ) P . L D . ions

C1 C1

37

4

4 1

PhCH + , B r B r PhCH (CH ) + , C.Br.Br P . I . D . ions

1 1 1 19

5 2 2 2 2

2

8 1

3

8 1

264.

2

9 8

1

2

n

2 3

2

3 2 5

2 1 1

1

2 15

4

1 6 16

8 1

C H Br Br , ( H C ) P h P h C H (CH ) -je t c . , H C C 0 4-, H C CH (C H ) 4 1 1 1 P . I . D . ions 1 1 2 14 2

2

2

7

3

2

3

3 3

1 3

7

1 7

n

C1 C1 4

37

P h O | R 4 H (rearr.), (F C) -triazine-CF f ; I C + H P . I . D . ions 3

2

2

2

2 3

T

266.

13 2 1 1 2

8 1

C H B r B r , H-j- cyclohexyl(CH )-CH (C H ) 4 R P . I . D . ions 3

265.

3 12

2 1

2

2

1 1 2 1 1 1 5 3 12


1 3 16

Mass

Spectral

m/e

Data

267-273


Formula

Relative Probability 2 3 4 6 6 7 8 9

l 267.

(Hg C ) PhOPhC (CH + , C H C10Ph ( C H ) C (CH ) + , . I ^ C , (H C) Pb-j-, I CH-j-,H C CO-j-; C C 1 F , (naphthyl),CH+ 3 P . I . D . ions 11 Other unclassified 4

3

6

3

4

3

2

2

17

4


9

2/

3

6

268.

(H C ) NCO-j-, (C F ) P . I . D . ions Other unclassified

269.

C H B r F , C^KÔ (m/e 251 steroid + HOH), BrBr CIPhfX; C i s H 2 i S i , C5 F n P . I . D . ions Other unclassified

17

6

8

2

4

8

9

1 1 1 1 3 2 13 1 1

1 2 2 4 1 1 3 1 2 1

6

8 1

2

3

1 1 1

2

1 1

270.

271.

C H 0 (m/e 255 steroid + =0), C F H g f ; CF PhPhCF +, Cl (PhOPh) - f X 1 9

2 7

3

3

2

3

3 7

x

272.

C C1 C1

273.

C ^ H ^ O (m/e 255 steroid + HOH), B r ( F C ) PhCF +; CgHBrBr F

5

5

=f= 2

1 1

3

2

81

4

1 1



88

m/e

°* ~ -a


Relative Probability ~ g •§ 1 2 3 4 5 6 7 8 9 10 pJ__P 13 1 14

274.

(C F )

275.

C C 1 C 1 F , H C -phenanthrene-C ( C H ) - k C Br*Cl F (CF CH 0) POOCH +; HgÔOCCHgOPhCl fCl 2 1

7

1 0

3 7

5

4

2

9

4

3

4

a

3

2

4 >

2

2

2


2

276.

277.

2

Cl Cl

3 7

2

4

1 1 8

2

37

Cl PhC Cl =j=Cl

1

;

C P h C C l f , etc., ( H C ) -cyclotrisiloxane -j- R, PhI^C C(Ph)(CH )f; B r B r -dihydrobenzofuran ^-, B r B r P h C (CH ), + , dibenzanthracene +fc 5

14

12 1 15

2

5

2

5

3

3

8 1

a

3

278.

H-j-C H -CH(C H ) f R

279.

C a H ^ B r j j B r , naphthylCH ( C H ) f , C HCl3Cl F

6

1 0

1 3

2 1

1

2 7

8 2 19

1 14 2 18

81

1 0

1 9 3 7

5

280.

1

H C a

1 0

4

C H ( C H ) =j= (H) R 9

1 8

1

1 1 2

9 1 15

1


13

14

Mass

Spectral

Data

m/e

274-290

89

°' - -a m/e

281.


Relative Probability h O 1 2 3 4 5 6 7 8 9 10 D_ H_

(H,, C ) Si 0< -j-R, H , C (H C )„Pb + , (H C,) (PhPh)4, C H F 0; H C PhOPhC H 4, 7

4

5

7

9

5

l s

2

s

8

6

2

4

H J ^ C J Q C H (CnHjg) -j 9 -

3 7

Cl Cl PhSf, C F 4

6

U

2

11

1 1 1 3 10


282.

13 3 16

283.

BrBr*PhCHCl|

284.

CeClgCl

285.

20

1

37

3

TetrahydronaphthylCH (CioH*) { , C H F 0 8

2

9

286.

PhBi=j=R ,

287.

H^C^CHPh-j-

2

8

1

1

(C F ) 8

3 2 6

3

1

10

1

11

5

10 1 12

13

5

288.

6

6

289.

1 1 2

290.

5 In Mass Spectral Correlations; McLafferty, F.; Advances in Chemistry; American Chemical Society: Washington, DC, 1963.

5

A D V A N C E S IN CHEMISTRY

90

Q

m/e

291.


292.

293.

Structural Significance »

1

8 1

. - -a

Relative Probability ~ g -g j j 4 (J $ f ft* 9 io p, i d h

CgHBr^ClFe, decahydronaphthyl C H ^ H * ) -j-

BrBr

SERIES

1

13

Efe C PhO -f COR -f H (rearr.)

16

3

1

10

1 12

1 1 1 1

4

1 11

8

10

2 4

12

BrBr^HOjPhCfCH^f

C He B r Br* , C7F11; (naphthyl) 4

2

2

C=CHCH f, (ClHgCaO^SiClOCgHi-f- 1 1 2

294.

BrBr

8 1

H C PhO +COR + H (rearr.), H + ( H C ) CH ( C „ H ) + R 5

3

a D

l 0

1

a

295.

37

Cl PhOPSCl f, H C PhOPhC H f, (H C ) Pb+ etc.; ( H a C ^ C H f , etc. 3

1 3

6

5

3

2

6

3

2 1

1

11

296.

297.

7

C C1 C1 5

3

37

F

1

5

3

298.

299.

17

4

3 1 4

H C -pyrene-C ( C H ) f 9

4

3

2

1


2

3

M a s s Spectra/ Data

m/e

297-370

91

^

m/e

Structural Significance *

l

300.


301.

73

-

Relative Probability ~ o 2 i 3 4 5 6 7 « 9 l O j * £_ §_ 3 1 4

C HBrBrfCl

1

1

2

302.

1 2 3

303.

1 1 2

304.

None

305.

C F 8

1

1

U

4

306.

307.

[H C(H C )Ph-] CHf 3

9

4

5

1

1

6

1 1 1 4

308.

309.

310.

4

etc.,

2

C C1 C13T

5

H^C^CH^HJ-}-,

2

etc.

3

3 4 2 12

5


16

5

92


. , Significance ~. ... Structural

m/g


311.

C l C P h (CI) CC1C1

312.

(C F )

313.

Br Br

37

3

7

R g -g 73 i-s

Relative Probability 1

2

3

4

5

6

7

8

9

10 P J S H

- { - 2

1 3

6

1 2

8 1

2

3 7

4

1

4

314.

315.

C g H g B r B r f CI

1

5

3

4

2 2 4 (C F ) 9

n

318.

319.

13

5 1 6

316. 317.

17

Ph-j-X,

C C1 C1 F 5

SERIES

3 7

C C1 C1 , (C F ) 6

6

6

1 3

1

1

2

2

1

1

320.

1

1

321.

1

1



to

CO CO

o

o a

O M -J

8 td CO w to

CO CO CO

a

o

CO CO

o

CO CO

-a

a

~4~ o

CO CO

00

to

CO

CO CO

o o a~

^7

a «

^ o

CJ1

CO CO


a

*4

a

to

s a

CO CO

CO CO CO

CO CO CO

IS |P.I.D. J Unci. I Total

I

o

f

105

|C0

iro

•

CO

o

2

CO

to

CO CO

o Q

Q


94


m/e


J 73

^

Relative Probability iJ g -§ 1 2 3 4 5 6 7 6 9 10 pi

333.

1

1

334.

2

2

1

1

335.

None

336.

(C F )

337.

H ^ C * CH (C H ) f

9

1 2

2

1

5

1

338.

2

2

339.

2

2

340.

2 1 3

341.

BrgBr

8 1

PhCH (CH ) \ 3

1

342.

343.

BrjjBr C F 8

81

1 3

1

2

8

8

(HO) (H C) Ph + B r ; 3

1

1


3

5

Mass

Spectral

Data

m/e

333-354

95

R j 73 m/e —


344.

C Br Brf

2

4 1 7

345.

CjjHBrjjBrf

2

2

4

346.

8

8

347.

3

3

2

2

349.

1

1

350.

2 1 3

351.

1 1

2

2

^=X

2

348.

2

4-X,

I (HO)PhfX Publication Date: January 1, 1963 | doi: 10.1021/ba-1963-0040.ch001

Relative Probability g -g 1 2 ^ 4 5 6 7 8 9 10ft_^H_

(C F ) 1 0

1 2

352.

353.

2

2

1

1

None

354.


96


R ~ 73 m/e


355.


Relative Probability 1 2 3 4 5 6 7 8 9 10

Silicones, ( C F )

§ S

2

2

356.

2

2

357.

1

1

358.

4

4

9

81

359.

CgHgBrgBr -

360.

None

1 3

1

361.

1

1

1

364.

2

13

365.

2 1 3

362.

(C F )

363.

None

8

1 4


Mass

Spectral

Data

m/e

97

355-376

Q


m/e


366.

None

367.

(C

368.

Cholestene^ (H) OY (Y= -OH, -OCOR)

. ^ 73

Relative Probability ^ e © 1 2 3 4 5 6 7 8 9 10ft

F )

10

1 3

369.

(C F )

370.

Cholestane 4= (H) OY (Y= -OH, -OCOR)

7

11

2 4

1 5

371.

None

372.

None

373.

None

374.

(C F )

375.

None

376.

None

9

1

2

1

1 4


1

5


98


m/e


377.

None

378.

None

379.

(C F )

380.

None

381.

C F

382.

None

n

8

^ ^ -a Relative Probability ~ g -g 1 2 3 4 5 6 7 8 9 10 p i & H

1 1

1 3

1

1 5

1

2

1 1

383.

384.

None

385.

None

386.

(C F )

387.

None

1 0

1 4


Mass

Spectral

Data

m/e

99

377-398

J

D

m/e


Relative Probability 1 2 3 4 5 6 7 8 9 10 ^

1 1

388.

389.

None

2

2

1

1

394.

3

3

395.

1

1

396.

1

1

1

1

390. Publication Date: January 1, 1963 | doi: 10.1021/ba-1963-0040.ch001

-a

g -g H_

391.

None

392.

393.

397.

(C F ) 9

1 5

None

398.


100


6 399.

7

8

. c 9 10 ft 13

SERIES

1o H

None

4036 3926 3864 1728 883 387 184 119 107 112 349 51 15, 746


Grand Total


Mass

Spectral

Data

m/e

m/e

399-417

Ion

400. * 401.

8 1

C B r B r F (6th peak) 4

2

6

402. 403.


404. 405.

C

1 0

F

1 5

406. 407. 408. 409. 410. 411. 412.

C F 9

1 6

413. 414. 415. 416. 417.

CnFxs

* Above m/e 400 there are only 20 P . I . D . and unclassified entries in the Dow punched card file. In Mass Spectral Correlations; McLafferty, F.; Advances in Chemistry; American Chemical Society: Washington, DC, 1963.


102

Ion

m/e 418. 419. 420.


421. 422. 423. 424.

C

F

1 0

16

425. 426. 427. 428. 429.

Silicones

430. 431.

C

9

F

1 7

432. 433. 434. 435. 436.

C

l l

F

1 6


SERIES

Mass

Spectral

Data

m/e

m/e

418-455

Ion

437. 438. 439. 440.


441. 442. 443.

C

1 0

F

1 7

444. 445. 446. 447.

C Br Brf

448.

C

4

1 2

3

F

(1st peak)

1 6

449. 450. 451. 452. 453. 454. 455.

C„ F

1 7


103

ADVANCES

104

m/e


Ion

456. 457. 458.


459. 460. 461. 462.

C F 1 0

1 8

463. 464. 465. 466. 467.

C

F

1 2

1 7

468. 469.

C F 9

1 9

470. 471. 472. 473. 474.

C F U

1 8


Mass

Spectral

Data

m/e

456-493

Ion

m/e 475. 476. 477.


478. 479. 480. 481.

C

F

1 0

1 9

482. 483. 484. 485. 486.

C

F

1 2

1 8

487. 488. 489. 490. 491. 492. 493.

C

u

F

1 9



106

Ion

m/e 494. 495. 496.


497. 498. 499. 500. 501. 502. 503. 504. 505.

C

1 2

F

1 9

506. 507. 508. 509. 510. 511. 512.

Ctt F

2


SERIES

Mass

Spectral

Data

m/e

494-531

Ion

m/e

513. 514. 515. 516.


517.

C

13

F

19

518. 519. 520. 521. 522. 523. 524.

C

12

F

20

525. 526. 527. 528. 529. 530. 531.

C

l l

F

21


107

108

ADVANCES IN CHEMISTRY SERIES

m/e

Ion

532. 533. 534.


535. 536.

C^F»

537. 538. 539. 540. 541. 542. 543.

C

1 2

F

a

544. 545. 546. 547. 548. 549. 550. In Mass Spectral Correlations; McLafferty, F.; Advances in Chemistry; American Chemical Society: Washington, DC, 1963.

Mass

Spectral

Data

m/e

Ion

551. 552. 553.


554. 555.

F

2i

556. 557. 558. 559. 560. 561. 562.

C

1 2

F

2 2

563. 564. 565. 566. 567.

C

1 4

F

a

568. 569. In Mass Spectral Correlations; McLafferty, F.; Advances in Chemistry; American Chemical Society: Washington, DC, 1963.


110

Ion 570. 571. 572. 573.


574.

C

13

F

2

575. 576. 577. 578. 579. 580. 581.

^12

^23

582. 583. 584. 585. 586. 587. 588. In Mass Spectral Correlations; McLafferty, F.; Advances in Chemistry; American Chemical Society: Washington, DC, 1963.

Mass Spectral

Data

m/e

570-617

Ion

m/e 589. 590. 591. 592.


593.

C

F

1 3

2

594. 595. 596. 597. 598. 599. 600.

605.

C F l 4

2:

610.

615. 617.

C

1 5

F

2 3


111

112


Ion

m/e 620.

625.


630. 631.

Cl3 25 F

635.

640. 643.

C

1 4

F

2

645.

650.

655.

660.

665.

670.

675. In Mass Spectral Correlations; McLafferty, F.; Advances in Chemistry; American Chemical Society: Washington, DC, 1963.

Mass

m/e

Spectral

Data

m/e

620-735

Ion

680.

685.


690.

695.

700.

705.

710.

715.

720.

725.

730.


114

m/e

ADVANCES

IN CHEMISTRY

Ion

740.

745.


750.

755.

760.

765.

770.

775.

780.

785.

790.


SERIES

Mass

Spectral

m/e

Data

m/e

740-1075

Ion

800.

825.


850.

875.

900.

925.

950.

975.

1000.

1025.

1050.


115

116

m/e

ADVANCES

IN CHEMISTRY

Ion

1100.

1125.


1150.

1175.

1200.

1250.

1300.

1350.

1400.

1450.

1500.


SERIES

Mass

Spectral

m/e

Data

m/e

7100-2000

Ion

1700.

1800.


1900.

2000.


Mass Spectral Correlations (1963 Edition)

Mass Spectral Correlations

A beginner's guide to mass spectral interpretation

Resebua Correlations

Oral Pathology: Clinical Pathologic Correlations, 6th Edition

Clinical Chemistry: Techniques, Principles, Correlations, 6th Edition

Mass Media and the Shaping of American Feminism, 1963-1975

Spectral

Spectral

Clinical Chemistry: Techniques, Principles, Correlations, 6th Edition

Фантастика-1963

Planar Ising Correlations

Correlations and SOC PhysicaA

Notes on Spectral Theory - Second Edition

Chebyshev and Fourier Spectral Methods, Second Edition

Processes with Long-Range Correlations

Epilepsy: Animal and Human Correlations

Correlations in Rosenzweig and Levinas

Planar Ising Correlations

Correlations of Soil Properties

Каталог 1933—1963

Искатель. 1963. Выпуск №5

Том 3. 1961-1963

Сверхвысокий вакуум. (Ultrahochvakuum, 1963)

Искатель. 1963. Выпуск №3

22 11 1963

Spectral Theory

Spectral Theory

Spectral Theory

Imaging of Brain Tumors with Histological Correlations, Second Edition

Искатель. 1963. Выпуск №1

Mass Spectral Correlations (1963 Edition)