Comprehensive Handbook of Chemical Bond Energies

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Dedication

Dr. Sidney W. Benson

who introduced me to the field of thermochemical kinetics during my postdoctoral work at the University of Southern California

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Preface Since the Handbook of Bond Dissociation Energies in Organic Compounds (CRC Press 2002) was published, users and colleagues have urged me to continue to update the experimental information and to extend the scope of BDE (bond dissociation energy or enthalpy) data to include not only organics but also other species such as inorganics, organometallics, biochemicals, radicals, ions, clusters, supramolecules, hydrogen-bonded species, surface-bonded, and van der Waals complexes. I believe that a new and complete version of the BDE database should be valuable for the following reasons: 1. Based on Chemical Abstracts, Web of Science, and Google Scholar, the measurement of BDEs is still one of the most active research topics. A great number of new experimental data are reported monthly. BDE data are continuing to be revised and updated. For example, the BDE values in even the simplest molecules such as H2O and NH3 have been revised recently and are now more reliable and accurate. 2. A large number of experimental BDE data of organometallic compounds are available, but they have not been collated. 3. The experimental BDEs in ions, clusters, hydrogen-bonded species, surfacebonded, and van der Waals complexes are essential data for catalysis, high-tech, nano-materials, bioengineering, environmental, and space science; however, these valuable data are dispersed throughout a variety of publications. Since the 1980s, the total number of experimental BDE data available has continued to sharply increase. We have collected the experimental BDE data of more than 19,600 bonds of 102 elements from 5,500 publications where the BDE data of about 2,000 bonds in organic species have been either updated or added. All of the new information is published in this series of volumes. I have introduced the BDE data of about 3,470 bonds in the CRC Handbook of Chemistry and Physics that is regularly updated. This enables the readers to cross-reference and find new details. The updated and enlarged version of this book will be an electronic publication in several years. The plan is to gather both measurements and predictions and to use a different font or color to distinguish between resources of the BDE values. I greatly appreciate the discussions and encouragement of the following individuals: Professors S. W. Benson (University of Southern California), J. L. Beauchamp (Cal Tech), P. B. Armentrout (University of Utah), R. H. Byrne (University of South Florida), G. B. Ellison (University of Colorado), W. E. Acree, Jr. (University of North Texas), D. M. Golden (Stanford University), T. Baer (University of North Carolina), J. F. Liebman (University of Maryland), P. W. Wenthold (Purdue University), S. E. Stein, M. Meot-Ner and D. R. Lide

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(National Institute of Standards and Technology), D. L. Hildenbrand (SRI International), B. M. Ruscic (Argonne National Laboratory), P. D. Pacey (Dalhousie University), J. L. Holmes (University of Ottawa), P. Kebarle (University of Alberta), J. A. Kerr (University of Birmingham), W. A. Brown (University College, London), J. P. Cheng (Nankai University), S. Q. Yu and Q. X. Guo (University of Science and Technology of China), H. L. Chen (Nanjing University), H. Schwarz (Technical University, Berlin), L. Schweikhard (Ernst Moritz Arndt University), S. P. Verevkin (University of Rostock, Germany), many scientists, engineers, and users. Comments and suggestions are welcome; please contact me by e-mail at [email protected].

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Preface to the primary version Three of the most fundamental concepts in organic chemistry are structure, energetics, and reactivity and their inter-relationships. Sometimes, attempting to discover reliable data on bond dissociation energies (BDEs) or the strengths of chemical bonds may be a frustrating exercise. I began to collect experimental and theoretical values for BDEs in 1990. Four years later, Dr. S. E. Stein of the National Institute of Standards and Technology (NIST) encouraged me to continue in this task that is essential for chemical kinetics, free radical chemistry, organic thermochemistry, and physical organic chemistry. A variety of methods exist for determining BDE values, but almost none are accurate to better than chemical accuracy (G1 kcal/mol, 1 calorie Z4.184 J). The BDE values of many important compounds have been measured many times; for example, the C–H BDE in methane has been determined about 50 times since the 1930s. BDE values continue to be a source of lively controversy among scientists. The data presented in this book are from experiments only, although theoretical calculations are very interesting. Collecting experimental BDE data has been like taking a class in the history of chemistry with many prominent scientists, including E. W. R. Steacie, L. Pauling, M. Szwarc, N. N. Semenov, and S. W. Benson, having made significant contributions to the problems surrounding the BDEs. I am very happy to acknowledge the great help, encouragement, and discussions of the following scientists in preparing this manuscript: Professors S. W. Benson, F. W. Bordwell, Y. T. Lee, R. H. Byrne, A. M. Dean, J. F. Liebman, V. D. Parker, and I. R. Slagle (United States); P. D. Pacey, J. L. Holmes, D. A. Armstrong, and E. Tschuikow-Roux (Canada); J. A. Kerr, R. Walsh, and M. J. Pilling (United Kingdom); C. Ru¨chardt (Germany); K. D. King (Australia); X. Z. Zhao and J. P. Cheng (China); A. J. Colussi (Argentina); J. A. M. Simo˜es (Portugal); J. A. Seetula (Finland); Drs. S. E. Stein and W. Tsang (NIST); T. J. Wallington (Ford Motor Company); M. Tirtowidjojo (Dow Chemical Company); K. U. Ingold and D. D. M. Wayner (NRC, Canada); and E. T. Denisov (Russia). I also would like to thank the reviewers for their suggestions and comments.

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Author Yu-Ran Luo, Ph.D., graduated from the University of Science and Technology of China and taught at the same university. He earned his doctoral degree from Dalhousie University in 1991. He has worked at the University of Ottawa, the University of Southern California, and NIST. Currently, he is a faculty member at the University of South Florida and is responsible for updating the BDE (bond dissociation energy) tables in the CRC Handbook of Chemistry and Physics. Since 1990, he has collected, assessed, and organized experimental BDE data. This handbook results from his industrious efforts of about seventeen years.

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List of notations and abbreviations AE AES AFM AOP AP BDE BIRD CERMS CID CL CPD CRDS CS MS DC DEA DELFINE detect. DH0 DLTS DROPS DSC DT EA ECD EELS EI EID EI-HP MS electrochem. EM ENDOR EPR ES ESDIAD

appearance energy measurements Auger electron spectroscopy atomic force microscopy acidity-oxidation potential measurements appearance potentials bond dissociation energy (or enthalpy) blackbody infrared radiative dissociation collision energy-resolved mass spectra collision-induced dissociation chemiluminescence concentration dependent diffusion cavity ring-down spectroscopy charge-stripping mass spectrometry diffusion coefficient dissociative electron attachment detection of laser fluorecence and ionization detection i.e., BDE, where H emphasizes the BDE is an enthalpy change of thermochemistry deep level transient spectroscopy double-resonance overtone photofragment spectroscopy differential scanning calorimetry drift tube experiments electron affinity electron capture detection electron energy loss spectroscopy electron impact ionization electron-induced decomposition elctrospray ionization-high pressure mass spectrometry electrochemical technique electron microscopy electron nuclear double resonance technique electron paramagnetic resonance spectrometry emission spectroscopy electron stimulated desorption ion angular distribution

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ESI ES MS ESR FA MS FA TQ FAB FDMS FDS FEM FIM FP FSEP FT-CR FT-ICR FT-MS FT-MW FT-IR FTR GC GDMS GIB MS GPA GPB G-S CG HAS HEED HPLC HP MS HR-EELS ICP ICR IMS IE (IP) IR IRAS IR MPD IR PD ISS KERD KIM MS LEED LEEM LEIS LF LI LID LIF LIPAC LITD LLD LMR

electrospray ionization electrospray mass spectrometry electron spin resonance spectrometry flowing afterglow mass spectrometry flowing afterglow-triple quadrupole technique fast atom bombardment flash decomposition mass spectroscopy flash decomposition spectroscopy field emission microscopy field ion microscopy flash photolysis femtosecond stimulated emission pumping Fourier transform cyclotron resonance spectrometry Fourier transform ion cyclotron resonance spectrometry Fourier transform mass spectrometry Fourier transform microwave spectrometry Fourier transform infrared spectrometry flow-tube reactor gas chromatographic analysis glow discharge mass spectrometry guided-ion beam mass spectrometry gas-phase acidity gas-phase basicity gas-solid chromatography helium atom scattering high-energy electron diffraction high performance liquid chromatography high-pressure mass spectrometry high-resolution electron energy loss spectroscopy inductively coupled-plasma mass spectrometry ion cyclotron resonance spectrometry ion mobility spectrometry ionization energy (potential) infrared spectrometry infrared reflection absorption spectroscopy infrared multiphoton dissociation infrared (multiphoton) photodissociation ion scattering spectroscopy kinetic energy release distribution kinetic ion mobility MS low energy electron diffraction low energy electron microscopy low energy ion scattering laser flash photolysis laser ionization laser-induced desorption laser-induced fluorescence laser-induced photoacoustic calorimetry laser-induced thermal desorption linear laser diffraction laser magnetic resonance spectroscopy

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LOD LP MALDI MATI MBE MBR MF MIKE MPI MRHEED MS MV ND NICI MS NMR OODR PA PAC PACS PACT PD PDS PE PED PEDt PEEM PFI-PEPICO PFI-PE PES PF PHOFEX photobromin. photochlorin. photodetach. photodissocn photoelectr. PI PIE PIMS PIPECO POSTS PPC PSD PST PTS PVT QP MS RAIRS RBS re-anal. re-cal.

linear optical diffraction laser photolysis matrix-assisted laser desorption ionization mass-analyzed threshold ionization spectra molecular beam epitaxy molecular beam relaxation spectroscopy metastable fractions mass analyzed ion kinetic energy spectrometry multi-photo ionization microprobe reflection high-energy electron diffraction mass spectrometry microwave neutron diffraction negative ion chemical ionization MS nuclear magnetic resonance spectrometry optical–optical double resonance proton affinity photoacoustic calorimetry perturbed angular correlation spectroscopy perturbed g–g angular correlation technique photodissociation photodissociation spectroscopy photoemission photoelectron diffraction photoelectron detachment photoemission electron microscopy pulsed field ionization photoelectron-photoion coincidence technique pulsed field ionization photoelectron technique photoelectron spectrometry photofragmentation photofragmentation excitation photobromination photochlorination photodetachment photodissociation photoelectron photoionization photoionization efficiency photoionization mass spectrometry photoion–photoelectron coincidence spectra position sensitive translational spectroscopy photoelectron–photofragment coincidence spectra photosensitized dissociation pulse shock tube photofragment translational spectrometry pressure–volume–temperature data analysis quadrupole mass spectrometer reflection adsorption infrared spectroscopy Rutherford backscattering spectrometry re-analysis of experimental data, i.e., revised re-calculated BDEs from experimental data, i.e., revised

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recommend. REM REMPI REPD RET RF RHEED RST R2PI SAMS SCAC SEI SEM SEP SHD SHG SID SIE SIFT SIMS S.P. spectrom. SPST STM TA TC TCT TD TDS TEAS TEM TFD TG TIPPS TOF-MS TPD TPEPICO TPR TPRS TP-ZEKE TQ MS TR-EELS TR-LIF TR-IR TR-PAC TR-PD VLPP VLPR VTAFM VUV UPS

recommended value reflection electron microscopy resonance enhanced multiphoton ionization resonance enhanced photodissociation spectroscopy reactive energy thresholds resonance fluorescence reflection high-energy electron diffraction reflected shock tube resonant 2-photo photoionization stationary afterglow-mass spectrometry single crystal adsorption calorimetry secondary electron imaging scanning electron microscopy stimulated emission pumping-resonant second harmonic diffraction second harmonic generation surface-induced dissociation secondary ion emission selected ion flow tube secondary ion mass spectrometry surface potentials spectrometry single-pulse shock tube technique scanning tunneling microscopy thermal analysis thermal conductivity toluene carrier technique thermal desorption (flash desorption) thermal desorption spectroscopy thermal energy atom scattering transmission electron microscopy thermal flash desorption thermal gravimetry threshold ion-pair production spectroscopy time-of-flight mass spectrometry thermal programmed desorption spectra threshold photoelectron photoion coincidence spectroscopy temperature programmed reaction temperature programmed reaction spectroscopy two-phototon zero-kinetic-energy (photoelectron spectra) triple-quadrupole mass spectrometer time-resolved electron energy loss spectroscopy time-resolved laser-induced fluorescence time-resolved infrared spectrometry time-resolved photoacoustic calorimetry time-resolved photodissociation very low pressure pyrolysis technique very low pressure reactor method variable-temperature atomic force microscopy vacuum ultraviolet ultraviolet photoelectron spectroscopy

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UV/VIS XPS ZEKE-PEI 2PPE

ultra-violet and visible spectrometry x-ray photoelectron spectroscopy zero kinetic energy pulsed field ionization photoelectron spectroscopy two-photon photoemission

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Contents Chapter one Introduction ........................................................................................................1 1.1 Comprehensive database of the BDEs ............................................................................1 1.2 What is the BDE? ................................................................................................................1 1.3 Why are reliable BDEs needed? .......................................................................................3 1.4 Scope of this book ...............................................................................................................3 1.5 On energy units ...................................................................................................................5 1.6 How to search for BDEs in this book ..............................................................................6 1.7 How to use the BDE data tables .......................................................................................7 Chapter two Experimental methods for measuring BDEs ...............................................13 2.1 A summary of main experimental methods ................................................................13 2.2 The conversion between D0, De, and DH0 ....................................................................16 2.2.1 Diatomic molecules .............................................................................................17 2.2.2 Polyatomic molecules .........................................................................................18 Chapter three BDEs of C–H bonds ......................................................................................19 3.1 Chain saturated hydrocarbons .......................................................................................19 3.2 Chain unsaturated hydrocarbons ...................................................................................24 3.3 Cyclic hydrocarbons .........................................................................................................31 3.4 Aromatic hydrocarbons ...................................................................................................40 3.5 Halogenated hydrocarbons .............................................................................................61 3.6 Organic compounds containing heteroatom(s) ............................................................70 3.6.1 C–H BDEs with a-OH, -OR, -C(O), -C(O)OH, -C(O)OR, -OC(O)R and -OOR ..............................................................................................................70 3.6.1.1 C–H BDEs with a-OH .......................................................................70 3.6.1.2 C–H BDEs with a-OR ........................................................................73 3.6.1.3 C–H BDEs with a-C(O) .....................................................................83 3.6.1.4 C–H BDEs with a-C(O)OH ..............................................................93 3.6.1.5 C–H BDEs with a-C(O)OR, -OC(O)R and -OOR ..........................96 3.6.2 C–H BDEs with a-N, -CN, -NC, -NO, -NO2, -NN and in heterocyclic species ...........................................................................................102 3.6.2.1 C–H BDEs with a-N ........................................................................102 3.6.2.2 C–H BDEs with a-CN and -NC .....................................................106 3.6.2.3 C–H BDEs with a-NO, -NO2, and -NN .......................................109 3.6.2.4 C–H BDEs in heterocyclic species .................................................112 3.6.3 C–H BDEs with a-O, -N and their groups ....................................................118

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3.7

3.6.4 C–H BDEs with a-C(S), -S, -SO, and -SO2 .....................................................125 3.6.5 C–H BDEs with other heteroatoms at a-position .........................................132 C–H BDEs in radicals .....................................................................................................134

Chapter four BDEs of C–C bonds ......................................................................................147 4.1 Saturated hydrocarbons .................................................................................................147 4.2 Chain unsaturated hydrocarbons .................................................................................154 4.3 Aromatic hydrocarbons .................................................................................................161 4.4 Halogenated hydrocarbons ...........................................................................................166 4.5 Organic compounds containing heteroatoms ............................................................178 4.5.1 Organic compounds containing oxygen atoms ............................................178 4.5.2 Organic compounds containing nitrogen atoms ..........................................191 4.5.3 Organic compounds containing sulfur atoms ..............................................203 4.6 C–C BDEs in radicals .....................................................................................................205 Chapter five BDEs of C–halogen bonds ............................................................................211 5.1 C–F bonds .........................................................................................................................211 5.2 C–Cl bonds .......................................................................................................................218 5.3 C–Br bonds .......................................................................................................................233 5.4 C–I bonds .........................................................................................................................243 Chapter six BDEs of O–X bonds .........................................................................................255 6.1 O–H bonds .......................................................................................................................255 6.1.1 O–H bonds in non-phenols ..............................................................................255 6.1.1.1 O–H bonds in ROH .........................................................................255 6.1.1.2 O–H bonds in RC(O)OH ................................................................262 6.1.1.3 O–H bonds in ROOH ......................................................................266 6.1.2 O–H bonds in oximes and hydrolamines ......................................................272 6.1.3 O–H bonds in phenols ......................................................................................285 6.1.4 O–H bonds in sterically hindered phenols ...................................................298 6.1.5 O–H bonds in metal-containing species ........................................................306 6.1.6 O–H bonds in radicals ......................................................................................308 6.2 O–O bonds .......................................................................................................................309 6.3 O–C bonds ........................................................................................................................321 6.3.1 O–C bonds in alcohols ......................................................................................321 6.3.2 O–C bonds in ethers ..........................................................................................325 6.3.3 O–C bonds in acids, esters and anhydrides ..................................................333 6.3.4 O–C bonds in peroxides and peroxys ............................................................337 6.3.5 O–C bonds in other species .............................................................................342 6.3.6 O–C bonds in radicals .......................................................................................346 6.4 O–N bonds .......................................................................................................................347 6.5 O–S bonds ........................................................................................................................360 6.6 O–halogen bonds ............................................................................................................365 Chapter seven BDEs of N–X bonds ...................................................................................369 7.1 N–H bonds .......................................................................................................................369 7.1.1 N–H bonds in non-anilines ..............................................................................369 7.1.2 N–H bonds in anilines ......................................................................................378 7.1.3 N–H bonds in cyclic compounds ....................................................................387 7.2 N–N bonds .......................................................................................................................395

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7.3 7.4 7.5 7.6

N–C bonds ........................................................................................................................403 N–S bonds .........................................................................................................................420 N–halogen bonds .............................................................................................................422 N–B, N–Al, N–Ga, and N–In bonds .............................................................................424

Chapter eight BDEs of S–, Se–, Te–, Po–X bonds .............................................................425 8.1 S–H bonds ........................................................................................................................425 8.2 S–S bonds .........................................................................................................................431 8.3 S–C bonds .........................................................................................................................436 8.4 S–halogen bonds .............................................................................................................445 8.5 S–P, S–As, and S–Sb bonds ............................................................................................449 8.6 Se–X bonds .......................................................................................................................451 8.7 Te–X bonds .......................................................................................................................453 8.8 Po–X bonds ......................................................................................................................454 Chapter nine BDEs of Si–, Ge–, Sn–, and Pb–X bonds ...................................................455 9.1 Si–X BDEs .........................................................................................................................455 9.2 Ge–X bonds ......................................................................................................................467 9.3 Sn–X bonds ......................................................................................................................473 9.4 Pb–X bonds ......................................................................................................................478 Chapter ten BDEs of P–, As–, Sb–, Bi–X bonds ...............................................................481 10.1 P–X bonds ......................................................................................................................481 10.2 As–X bonds ....................................................................................................................487 10.3 Sb–X bonds .....................................................................................................................489 10.4 Bi–X bonds .....................................................................................................................490 BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X bonds ..............................................................................493 C H–, H –, and HK–X bonds .........................................................................................493 Li– and LiG–X bonds ....................................................................................................496 11.2.1 Li–X bonds ......................................................................................................496 11.2.2 LiG–X bonds ...................................................................................................500 Na–, NaCK, and NaK–X bonds .................................................................................516 11.3.1 Na–X bonds ....................................................................................................516 11.3.2 NaC–X bonds .................................................................................................522 11.3.3 NaK–X bonds .................................................................................................541 K–, KC–, and K––X bonds ...........................................................................................541 11.4.1 K–X bonds .......................................................................................................541 11.4.2 KC–X bonds ....................................................................................................544 11.4.3 KK–X bonds ....................................................................................................557 Rb–, RbC–, and RbK–X bonds ....................................................................................557 11.5.1 Rb–X bonds .....................................................................................................557 11.5.2 RbC–X bonds ..................................................................................................559 11.5.3 RbK–X bonds ..................................................................................................562 Cs–, CsC–, and CsK–X bonds .....................................................................................563 11.6.1 Cs–X bonds .....................................................................................................563 11.6.2 CsC–X bonds ..................................................................................................565 11.6.3 CsK–X bonds ..................................................................................................569

Chapter eleven 11.1 11.2 11.3

11.4

11.5

11.6

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BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X bonds ........................................................................................571 Be– and BeC–X bonds ..................................................................................................571 12.1.1 Be–X bonds .....................................................................................................571 12.1.2 BeC–X bonds ..................................................................................................573 Mg– and MgC–X bonds ...............................................................................................574 12.2.1 Mg–X bonds ...................................................................................................574 12.2.2 MgC–X bonds ................................................................................................579 Ca– and CaC–X bonds .................................................................................................584 12.3.1 Ca–X bonds .....................................................................................................584 12.3.2 CaC–X bonds ..................................................................................................587 Sr– and SrC–X bonds ...................................................................................................591 12.4.1 Sr–X bonds ......................................................................................................591 12.4.2 SrC–X bonds ...................................................................................................593 Ba– and BaC–X bonds ..................................................................................................596 12.5.1 Ba–X bonds .....................................................................................................596 12.5.2 BaC–X bonds ..................................................................................................598 Ra–X bonds ....................................................................................................................599

Chapter twelve 12.1 12.2 12.3 12.4 12.5 12.6

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X bonds ...........................................................................601 C Sc– and Sc –X bonds ...................................................................................................601 13.1.1 Sc–X bonds ......................................................................................................601 13.1.2 ScC–X bonds ...................................................................................................603 Y– and YC–X bonds ......................................................................................................607 13.2.1 Y– bonds ..........................................................................................................607 13.2.2 YC–X bonds ....................................................................................................610 La– and LaC–X bonds ..................................................................................................612 Ac– and AcC–X bonds .................................................................................................643

Chapter thirteen 13.1 13.2 13.3 13.4

Chapter fourteen BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X bonds ........................667 14.1 Ti–, TiC–, and TiK–X bonds ........................................................................................667 14.1.1 Ti–X bonds ......................................................................................................667 14.1.2 TiC– and TiK–X bonds .................................................................................673 14.2 Zr– and ZrC–X bonds ..................................................................................................679 14.2.1 Zr–X bonds .....................................................................................................679 14.2.2 ZrC–X bonds ..................................................................................................683 14.3 Hf– and HfC–X bonds .................................................................................................685 Chapter fifteen BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds ...........................689 15.1 V–, VC–, and VK–X bonds ..........................................................................................689 15.1.1 V–X bonds .......................................................................................................689 15.1.2 VC–X bonds ....................................................................................................692 15.1.3 VK–X bonds ....................................................................................................699 15.2 Nb– and NbC–X bonds ................................................................................................700 15.2.1 Nb–X bonds ....................................................................................................700 15.2.2 NbC–X bonds .................................................................................................704 15.3 Ta– and TaC–X bonds ..................................................................................................708 15.3.1 Ta–X bonds .....................................................................................................708 15.3.2 TaC–X bonds ..................................................................................................711

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Chapter sixteen BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X bonds ......................713 16.1 Cr–, CrC–, and CrK–X bonds .....................................................................................713 16.1.1 Cr–X bonds .....................................................................................................713 16.1.2 CrC–X bonds ..................................................................................................723 16.1.3 CrK–X bonds ..................................................................................................733 16.2 Mo–, MoCK, and MoK–X bonds ...............................................................................734 16.2.1 Mo–X bonds ...................................................................................................734 16.2.2 MoC–X bonds ................................................................................................746 16.2.3 MoK–X bonds ................................................................................................751 16.3 W–, WC–, and WK–X bonds .......................................................................................751 16.3.1 W–X bonds ......................................................................................................751 16.3.2 WC–X bonds ..................................................................................................778 16.3.3 WK–X bonds ..................................................................................................780 Chapter seventeen BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X bonds ...................781 17.1 Mn–, MnC–, and MnK–X bonds .................................................................................781 17.1.1 Mn–X bonds ....................................................................................................781 17.1.2 MnC–X bonds .................................................................................................787 17.1.3 MnK–X bonds .................................................................................................793 17.2 Tc–X and TcC–X bonds .................................................................................................795 17.2.1 Tc–X bonds ......................................................................................................795 17.2.2 TcC–X bonds ...................................................................................................795 17.3 Re–, ReC–, and ReK–X bonds .....................................................................................796 17.3.1 Re–X bonds .....................................................................................................796 17.3.2 ReC–X bonds ..................................................................................................799 17.3.3 ReK–X bonds ..................................................................................................801 Chapter eighteen BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X bonds ....................803 18.1 Fe–, FeC–, and FeK–X bonds ......................................................................................803 18.1.1 Fe–X bonds .....................................................................................................803 18.1.2 FeC–X bonds ..................................................................................................815 18.1.3 FeK–X bonds ..................................................................................................838 18.2 Ru– and RuC–X bonds .................................................................................................840 18.2.1 Ru–X bonds ....................................................................................................840 18.2.2 RuC–X bonds .................................................................................................849 18.3 Os– and OsC–X bonds .................................................................................................851 18.3.1 Os–X bonds .....................................................................................................851 18.3.2 OsC–X bonds ..................................................................................................853 Chapter nineteen BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X bonds ......................855 19.1 Co–, CoC– and CoK–X bonds .....................................................................................855 19.1.1 Co–X bonds ....................................................................................................855 19.1.2 CoC–X bonds .................................................................................................868 19.1.3 CoK–X bonds .................................................................................................881 19.2 Rh– and RhC–X bonds .................................................................................................882 19.2.1 Rh–X bonds ....................................................................................................882 19.2.2 RhC–X bonds .................................................................................................892 19.3 Ir– and IrC–X bonds .....................................................................................................895 19.3.1 Ir–X bonds .......................................................................................................895 19.3.2 IrC–X bonds ...................................................................................................901

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Chapter twenty BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X bonds .........................903 20.1 Ni–, NiC–, and NiK–X bonds .....................................................................................903 20.1.1 Ni–X bonds .....................................................................................................903 20.1.2 NiC– and NiK–X bonds ...............................................................................921 20.1.3 NiK–X bonds ..................................................................................................931 20.2 Pd–, PdC–, and PdK–X bonds ....................................................................................932 20.2.1 Pd–X bonds .....................................................................................................932 20.2.2 PdC–X bonds ..................................................................................................939 20.2.3 PdK–X bonds ..................................................................................................941 20.3 Pt–, PtC–, and PtK–X bonds .......................................................................................941 20.3.1 Pt–X bonds ......................................................................................................941 20.3.2 PtC–X bonds ...................................................................................................963 20.3.3 PtK–X bonds ...................................................................................................965 Chapter twenty-one BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X bonds ...........967 21.1 Cu–, CuC–, and CuK–X bonds ...................................................................................967 21.1.1 Cu–X bonds ....................................................................................................967 21.1.2 CuC–X bonds .................................................................................................982 21.1.3 CuK–X bonds .................................................................................................989 21.2 Ag–, AgC–, and AgK–X bonds ...................................................................................990 21.2.1 Ag–X bonds ....................................................................................................990 21.2.2 AgC–X bonds .................................................................................................999 21.2.3 AgK–X bonds ...............................................................................................1009 21.3 Au–, AuC–, and AuK–X bonds ................................................................................1009 21.3.1 Au–X bonds ..................................................................................................1009 21.3.2 AuC–X bonds ...............................................................................................1021 21.3.3 AuK–X bonds ...............................................................................................1025 Chapter twenty-two BDEs of Zn(ZnC)–, Cd(CdC)–, and Hg(HgC)–X bonds .........1027 22.1 Zn– and ZnC–X bonds ...............................................................................................1027 22.1.1 Zn–X bonds ..................................................................................................1027 22.1.2 ZnC–X bonds ...............................................................................................1031 22.2 Cd– and CdC–X bonds ..............................................................................................1033 22.2.1 Cd–X bonds ..................................................................................................1033 22.2.2 CdC–X bonds ...............................................................................................1035 22.3 Hg– and HgC–X bonds ..............................................................................................1036 22.3.1 Hg–X bonds ..................................................................................................1036 22.3.2 HgC–X bonds ...............................................................................................1039 BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X bonds ...........................................................................1041 C K B–, B –, and B –X bonds .........................................................................................1041 23.1.1 B–X bonds .....................................................................................................1041 23.1.2 BC–X bonds ..................................................................................................1049 23.1.3 BK–X bonds ..................................................................................................1051 Al–, and AlG–X bonds ...............................................................................................1052 23.2.1 Al–X bonds ...................................................................................................1052 23.2.2 AlC– and AlK–X bonds ..............................................................................1062

Chapter twenty-three 23.1

23.2

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23.3

23.4 23.5

Ga–, GaC–, and GaK–X bonds .................................................................................1068 23.3.1 Ga–X bonds ..................................................................................................1068 23.3.2 GaC–X bonds ...............................................................................................1074 23.3.3 GaK–X bonds ...............................................................................................1075 In– and InG–X bonds .................................................................................................1075 23.4.1 In–X bonds ....................................................................................................1075 23.4.2 InC– and InK–X bonds ...............................................................................1083 Tl– and TlG–X bonds .................................................................................................1084 23.5.1 Tl–X bonds ....................................................................................................1084 23.5.2 TlC– and TlK–X bonds ...............................................................................1086

Chapter twenty-four 24.1

24.2 24.3 24.4 24.5

BDEs in the C-, Si-, Ge-, Sn-, Pb-clusters and complexes ...............................................................................1087 Carbon and the ion clusters/complexes .................................................................1087 24.1.1 Carbon clusters/complexes .......................................................................1087 24.1.2 Positive carbon-ion clusters/complexes ..................................................1099 24.1.3 Negative carbon-ion clusters/complexes ................................................1136 Silicon and the ion clusters/complexes ..................................................................1140 24.2.1 Silicon clusters/complexes ........................................................................1140 24.2.2 Silicon-ion clusters/complexes .................................................................1147 Germanium clusters/complexes ..............................................................................1153 24.3.1 Germanium clusters/complexes ...............................................................1153 24.3.2 Germanium-ion clusters/complexes ........................................................1155 Tin clusters/complexes ..............................................................................................1156 24.4.1 Tin clusters/complexes ..............................................................................1156 24.4.2 Tin-ion clusters/complexes .......................................................................1157 Lead clusters/complexes ...........................................................................................1159

Chapter twenty-five 25.1

25.2 25.3 25.4 25.5

BDEs in the N-, P-, As-, Sb-, Bi-clusters and complexes ................................................................................1163 Nitrogen and the ion clusters/complexes ..............................................................1163 25.1.1 Nitrogen clusters/complexes ....................................................................1163 25.1.2 Positive nitrogen-ion clusters/complexes ...............................................1171 25.1.3 Negative nitrogen-ion clusters/complexes .............................................1219 Phosphorus clusters/complexes ..............................................................................1235 25.2.1 Phosphorus-cation clusters/complexes ...................................................1235 25.2.2 Phosphorus-anion clusters/complexes ....................................................1236 Arsenic clusters/complexes ......................................................................................1238 Antimony clusters/complexes ..................................................................................1239 Bismuth-ion clusters/complexes ..............................................................................1240

Chapter twenty-six BDEs in the O-, S-, Se-, Te-clusters and complexes ...................1243 26.1 Oxygen and the ion clusters/complexes ................................................................1243 26.1.1 Oxygen clusters/complexes ......................................................................1243 26.1.2 Positive oxygen-ion clusters/complexes .................................................1259 26.1.3 Negative oxygen-ion clusters/complexes ...............................................1300 26.2 Sulfur and the ion clusters/complexes ...................................................................1323 26.2.1 Sulfur clusters/complexes .........................................................................1323 26.2.2 Positive sulfur-ion clusters/complexes ...................................................1325 26.2.3 Negative sulfur-ion clusters/complexes .................................................1331

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26.3 26.4

Selenium clusters/complexes ...................................................................................1341 Tellurium clusters/complexes ..................................................................................1346

Chapter twenty-seven 27.1

27.2

27.3

27.4

27.5

BDEs in the halogenated molecules, clusters and complexes .............................................................................1351 F–, FC–, and FK–X bonds ..........................................................................................1351 27.1.1 F–X bonds ......................................................................................................1351 27.1.2 FC–X bonds ...................................................................................................1355 27.1.3 FK–X bonds ...................................................................................................1355 Cl–, ClC–, and ClK–X bonds .....................................................................................1374 27.2.1 Cl–X bonds ....................................................................................................1374 27.2.2 ClC–X bonds .................................................................................................1377 27.2.3 ClK–X bonds .................................................................................................1379 Br–, BrC–, and BrK–X bonds .....................................................................................1399 27.3.1 Br–X bonds ....................................................................................................1399 27.3.2 BrC–X bonds .................................................................................................1401 27.3.3 BrK–X bonds .................................................................................................1402 I–, IC–, and IK–X bonds .............................................................................................1414 27.4.1 I–X bonds ......................................................................................................1414 27.4.2 IC–X bonds ...................................................................................................1416 27.4.3 IK–X bonds ...................................................................................................1417 At–X bonds ...................................................................................................................1427

Chapter twenty-eight BDEs in rare gas atom/ion clusters ..........................................1429 28.1 Rare gas atom clusters ...............................................................................................1429 28.1.1 Diatomic clusters .........................................................................................1429 28.1.2 Polyatomic clusters .....................................................................................1436 28.2 Rare gas ion clusters ...................................................................................................1446 Chapter twenty-nine Heats of formation of atoms, radicals, and ions ......................1453 29.1 Gaseous atoms .............................................................................................................1453 29.2 Small inorganic radicals in the gas-phase ..............................................................1455 29.2.1 Metallic radicals ...........................................................................................1455 29.2.2 Non-metallic radicals ..................................................................................1459 29.3 Organic radicals in the gas-phase ............................................................................1461 29.3.1 C-centered radicals ......................................................................................1461 29.3.2 O-centered radicals .....................................................................................1471 29.3.3 N-centered radicals .....................................................................................1474 29.3.4 S-centered radicals ......................................................................................1475 29.3.5 Si, Ge-, Sn-, and Pb-centered radicals ......................................................1476 29.4 Group additivity values for organic radicals .........................................................1478 29.5 Enthalpy of formation of monoatomic cations ......................................................1481 29.6 Enthalpy of formation of monoatomic anions .......................................................1484 References .................................................................................................................................1487 1946–1964 ..................................................................................................................................1487 1965–1969 ..................................................................................................................................1489 1970–1974 ..................................................................................................................................1494 1975–1979 ..................................................................................................................................1502 1980–1984 ..................................................................................................................................1511

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1985–1989 1990–1994 1995–1999 2000–2004 2005–2006

..................................................................................................................................1524 ..................................................................................................................................1540 ..................................................................................................................................1564 ..................................................................................................................................1591 ..................................................................................................................................1614

Index of compound classes ....................................................................................................1621 Index of compound names ....................................................................................................1633

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chapter one

Introduction 1.1

Comprehensive database of the BDEs

Chemistry and biochemistry are based upon the concept of chemical bonds. Because most chemical reactions involve the breaking and making of chemical bonds, chemists, biochemists, and chemical engineers need a complete database of the experimental data of bond dissociation energies (BDEs). This book collects, classifies, reorganizes, assembles, compares, and recommends the experimental BDE data of more than 19,600 bonds of 102 elements from over 5,500 publications. It is the most comprehensive book on the BDE data in all various reactants: biatomic molecules;

polyatomic molecules;

organic compounds;

inorganic compound;

organometallics;

biochemicals;

radicals;

ions;

clusters;

supramolecules;

hydrogen-bonded species;

surface-bonded species;

van der Waals complexes;

the isotopic species.

These detailed arrangements can help end-users performing a quick search for experimental BDE data.

1.2

What is the BDE?

The homolytic BDE is defined as the enthalpy change in the following fission: R

X/ R C X:

(1.1)

The BDE, DH0(RKX), of a RKX bond is derived in the usual way from the heats of formation of the species involved in the above reaction: DH0 ðR

XÞ Z Df H0 ðRÞ C Df H0 ðXÞKDf H0 ðRXÞ:

(1.2)

In this case, DfH0 represents the heats of formation of the respective species in the ideal gas state at standard pressure and at a reference temperature of 298.15 K. 1

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2

Comprehensive Handbook of Chemical Bond Energies

Therefore, the BDE is also called the bond dissociation enthalpy. Here, species RX represent molecules, radicals, ions, and complexes, as well as clusters. The BDEs are commonly referred to as bond energies, bond strengths, binding energies, or bond disruption energies (enthalpies). The BE or D are other simplified abbreviation of the BDE in the literature. The terms bond strength or binding energy are also widely used in scientific literature. For example, bond strength is frequently used to describe dentins, glasses, ceramics, resins, adhesives, and coatings; whereas, binding energy is used to describe selected electronic levels in atoms. Clearly, the binding energy or bond strength in these cases is not equivalent to the bond dissociation energy (enthalpy) in this volume. In this volume, varied processes of the bond dissociation are included, such as: Bond Dissociation Processes RKX/RCX (neutrals) RCKX/RCCX (cations) RKKX/RKCX (anions)

Examples CH4/CH3CH; Fe(CO)5/Fe(CO)4CCO (H3O)C(H2O)5/(H3O)C(H2O)4CH2O; FeC(CO)5/ FeC(CO)4CCO (NO2)K(CO2)5/(NO2)K(CO2)4CCO2; FeK(CO)4/ FeK(CO)3CCO

The BDEs in cations and anions can be derived based on the BDEs in naturals, ionization energy (IE), and electron affinity (EA): DH0 ðRCKXÞ Z Df H0 ðRCÞ C Df H0 ðXÞKDf H0 ðRCXÞ Z DH0 ðRKXÞ C IEðRÞKIEðRXÞ

(1.3)

DH0 ðRKKXÞ Z Df H0 ðRKÞ C Df H0 ðXÞKDf H0 ðRKXÞ Z DH0 ðRKXÞKEAðRÞ C EAðRXÞ:

(1.4)

Currently, heats of formation, DfH0(RX), of more than 7,000 compounds are known. Most of them are available in the following publications: 1996GUR/VEY, 1994FRE/KAB, 1994PED, 1991GUR/VEY, 1989COX/WAG, 1988LIA/BAR, 1986PED/NAY, and two websites (1996NIST, 2003YUN). Additionally, two websites, 2001IUPAC and 2003NASA/JPL, provide critical evaluated data. The experimental uncertainty in compounds’ heats of formation is generally within chemical accuracy (i.e., G1 kcal/mol, 1 calorieZ4.184 J). From Equation 1.2, measurements of BDEs are equivalent to measurements of heats of formation of free radical or ions, and vice versa. Experimental BDEs can be derived directly from Equation 1.2. For example, we may derive the BDE values of CH3–X, C2H5–X, where XZH, F, Cl, Br, I, OH, SH, NH2, CN, NO, NO2, CH3, and C2H5, if DfH0(CH3) and DfH0(C2H5) are known. From that point, we can derive more data of DH0(RCKX) and DH0(RKKX) by using Equation 1.3 and Equation 1.4. The number of confirmed compounds is close to thirty million (2006CAS). We must estimate the heats of formation of compounds and BDEs using ab initio MO theory, density functional theory (DFT), semi-empirical methods (such as PM3 and AM1), molecular mechanics, group additivity, and others. Burcat’s e-publication (2001BUR) and

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Introduction

3

NIST website (2002NIST/COM) provide more information about calculated BDEs, respectively. Although theoretical calculations are interesting and important, calculated BDEs are not included in this book.

1.3

Why are reliable BDEs needed?

The earlier experimental BDE data were collected by the previous publications: 1946STE, 1950SZW, 1958COT, 1958SEM, 1962MOR, 1966VED/GUR, 1968GAY, 1970DAR, 1974GUR/KAR, and 1979HUB/HER. Since the 1980s, almost all the BDE data have been updated. For example, the H–C BDE value in benzene increases to 111.2G 0.8 kcal/mol (1994BER/ELL) from 102 (1966VED/GUR) and 109.3 kcal/mol (1974GUR/KAR). The C–C BDE value in ethane increases to 90.2G0.2 kcal/mol (see Table 4.1) from 86G2 (1966VED/GUR) and 88.3G2.0 kcal/mol (1974GUR/KAR). The recommended value of the H–OH BDE in water is also updated to 118.81G 0.07 kcal/mol (2002RUS/WAG) from 119.2G0.2 (1970DAR) and 119.30G0.05 kcal/mol (1994BER/ELL). The equilibrium constant Keq is very sensitive to any error in the BDEs. An error of 1, 2, or 3 kcal leads to an error of a factor of 5.4, 29.2, or 158, respectively, in the equilibrium constant Keq at 298 K. The current experimental uncertainty of absolute majority of BDE data is within 1–2 kcal/mol; therefore, the uncertainty is greater than chemical accuracy (G1 kcal/mol). Experimental BDE values will continue to be a source of lively controversy among scientists now and in the foreseeable future. The current experimental uncertainty for H–H, H–D, and D–D BDEs is G0.0001 kcal/mol (see 2004ZHA/CHE, or Table 11.1 in chapter 11). DH0 ðH–HÞ Z 104:1539 G 0:0001 kcal=mol or 435:7799 G 0:0001 kJ=mol DH0 ðH–DÞ Z 104:9767 G 0:0001 kcal=mol or 439:2223 G 0:0002 kJ=mol DH0 ðD–DÞ Z 105:9560 G 0:0001 kcal=mol or 443:3197 G 0:0003 kJ=mol Several senior reviewers have made efforts to update known BDEs rapidly, such as 1966KER, 1969GOL/BEN, 1970ONE/BEN, 1978BEN, 1982MCM/GOL, 1986KEE/CAS, 1988COL, 1990SIM/BEA, 1994BER/ELL, 1994NOL, 1996CER, 1996FRE, 1996TSA, 1999COH, 2003BLA/ELL, and 2003OPE/RAB. However, the number of experimental BDEs is increasing sharply. We now have collected experimental data on over 19,600 bonds of 102 elements. A new publication that completely compiles all available BDEs will be of benefit to chemists, biochemists, and chemical engineers.

1.4

Scope of this book

The experimental BDEs of many important compounds have been measured many times. A typical example is C–H BDE in methane. It has been reported as many as fifty times since the 1930s, and the value spans from an early 98 kcal/mol to the current 105.0G0.1 kcal/mol. Although we have collected experimental data, it is not necessary to include all of the data in this book because most users are concerned with reliable experimental values only.

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Comprehensive Handbook of Chemical Bond Energies

This book will present recent experimental data for the given bonds, up to a maximum of five values for each bond. It is hard to state definitively the most reliable data for the BDEs. Recent measurements tend to be more generally reliable. Readers may search more experimental data using the references listed. The BDEs have been tabulated based on the center atom in the radicals, ions, clusters and complexes. This volume collects the experimental BDEs in all varied reactants. The scope is shown as:

Does This Book Include Them?

Species and Energetics

Other Database

BDEs in diatomic molecules and ions BDEs in organic compounds (including C–, O–, N–, S–, Si–, Ge–, Sn–, Pb–, P–, As–, Sb–, Bi–, Se–, and Te–X bonds)

Neutral

BDEs in inorganic compounds

Neutral Ions Neutral Ions Neutral Ions Metallic Non-metallic

BDEs in organometallic species

BDEs in clusters

Ions Yes

Supramolecules Hydrogen-bonded species Surface-bonded complexes Van der Waals complexes Proton affinities (PA) of species Electron affinities (EA) of species Ionization energies (IE) of species

No

(1) 1998HUN/LIA (2) 1988LIA/BAR (3) 1996NIST

The enthalpy change of the following processes is beyond the scope of this book. The readers may use relative databases for searching these data. In fact, the enthalpy change for these processes is related to the BDE:

Dissociation Processes RH/RKCHC RX/RCCXK RH/RCCHK

Examples and the Relations to BDEs Gas-phase acidity, GPAZDacidH(RKH)ZDH0(RKKHC)ZDH0(RKH)KEA(R)CIE(H) Heterolytic DH0(RCKXK)ZDH0(RKX)KEA(X)CIE(R) Hydride affinity, HAZDH0(RC–HK)ZDH0(RKH)KEA(H)CIE(R)

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Introduction

RHC/RCHC R/R%CCeK RK/ RCeK

5

Proton affinity (Gas-phase basicity), PAZGPBZDH0(RKH)CIE(H)KIE(RH) Ionization energy, IE(R) Electron affinity, EA(R)

This book is divided four sections: 1. Chapter 1 and Chapter 2 are the Introductions. Chapter 3 through Chapter 28 are the main body of this book. 2. Chapter 3 through Chapter 10 present C–, O–, N–, S–, Si–, Ge–, Sn–, Pb–, P–, As–, Sb–, Bi–, Se–, and Te–X BDEs in the molecules and radicals. 3. Chapter 11 through Chapter 24 deliver experimental BDEs in inorganics, organometallics, ions, clusters, supramolecules, hydrogen- and surface-bonded species, van der Waals complexes, and isotopic species.

The BDEs in C–, Si–, Sn–, Pb–, N–, P–, As–, Sb–, Bi–, O, S–, Se–, Te–, and halogen-clusters or complexes are presented in Chapter 25 through Chapter 28, respectively. The arrangements of BDE data in these neutral, cations, anions, clusters, and complexes are shown in the following Periodic Table. Here the numbers represent chapters of the BDE data for these bonds. 4. Chapter 29 summarizes the heats of formation of atoms, inorganic and organic radicals, and monoatomic cations or anions in the gas-phase.

1.5

On energy units

The SI unit of energy is joule (1 calorieZ4.184 joules). There are three options for energy units: joule only, calories only, and both units. Using both units is a better choice.

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Comprehensive Handbook of Chemical Bond Energies

Why? There are three reasons: (1) most heats of formation of radicals, ions and BDEs used to be measured in kcal/mol, and (2) the range of the BDE values for common organic K K species is from about 20 (as NaC–H2O, NHC 4 –NH3 , (HO4S) –H2O, NO2 –SO2 ) to 110 (as H–C6H5, H–C2H3) kcal/mol. As you know, a lower number is easy to remember in our everyday life, it is also the same in science. For example, we may easily remember 105.0 kcal/mol of H–CH3 BDE rather than 439.3 kJ/mol. (3) Most users prefer both units. Traditional energy units (e.g., cmK1, eV, au, K, kcal/mol) are still used in many publications for measurements and calculations of BDEs. Therefore, the energy conversion between non-SI (traditional) and SI units frequently needs to be made. The table of the energy conversion is shown in Table 1.1.

Table 1.1 Energy Conversion Factors between Non-SI (Traditional) and SI Units for the BDEs cmK1

eV

au

K

(wave number) (electron volt) (atomic unit) (Kelvin) 1 cmK1Z(for

1

1.239842(K4)

4.556335(K6) 1.438769

kcal/mol

kJ/mol

2.85914(K3)

1.196266(K2)

spectroscopy)

1 eVZ(for mass

8.06554(C3)

1

3.674931(K2) 1.16045(C4) 2.30605(C1)

9.64853(C1)

spectrometry)

1 hartree (au)Z(for

2.194746(C5)

2.72114(C1)

1

3.15773(C5) 6.27510(C2)

2.62550(C3)

theoretical calculations)

1 KZ(for theoretical 6.95039(K1)

8.61738(K5)

3.16683(K6)

1

1.98722(K3)

3.49755(C2)

4.33641(K2)

1.59360(K3)

8.35935(C1)

1.036427(K2)

3.808798(K4) 1.20272(C2) 2.39006(K1)

8.31451(K3)

physics)

1 kcal/molZ(for

5.03217(C2)

1

4.184

calorimetry)

1 kJ/molZ(SI unit)

1

Numbers in parentheses denote powers of 10 by which the entry is to be multiplied. More details are available in 2002CRC.

1.6

How to search for BDEs in this book

In creating this handbook, the authors encountered a large number of experimental BDEs from several thousand publications. The data are like goods in a large department store; they should be organized in different locations for research’s purposes. In this book,

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Introduction

7

these data are managed in various categories. The chemical bonds with most similar structural environmentals are assembled in tables. There are 225 separated tables for BDE data in this book. All tabulated values of the BDEs are systematized by the following eight orders:

1. Bond class such as C–H, C–C, C–O, C–N, C–S, C–F, C–Cl, C–Br, C–I, and so on. 2. Hetoroatom(s) and functional group(s) at a-position (relative to the broken bond) such as O, CO, C(O)O, N, CN, NO, NO2, NN, S, SO, SO2, and more. The heteroatom(s) and function group(s) have significant influence on the BDEs. Organic chemistry is usually organized by the concept of functional groups. Therefore, users must first figure out heteroatom(s) and functional group(s) before searching the data. For example, † The primary C–H BDE in C6H5CH2–H is listed in Table 3.4. In this book, the boldface emphasizes the dissociated atom or group. † The secondary C–H BDE in PhCH2COCH3 is listed in Table 3.6.1. There is a CO group at the a-position of the C–H bond. † The secondary C–H BDE in PhCOCH2NMe2 is listed in Table 3.6.3. There are a CO group and an N atom at the a-position of the C–H bond. † The secondary C–H BDE in PhCOCH2SO2Ph is listed in Table 3.6.4. There are a CO group and a SO2 group at the a-position of the C–H bond. 3. Bond order (triple, double, and single) and the bond degree (primary, secondary, or tertiary). The compounds with triple bond and primary BDEs are listed first. 4. Saturated or unsaturated compounds. Saturated ones are listed first. 5. Molecular size. The BDEs of smaller molecules are arranged first. 6. Molecular shape (chain or cyclic). The BDEs of chain molecules are arranged first. 7. While substituent(s)-containing, please first search the bonds in the parent molecules. For example, the C–H BDEs in substituted toluene are listed under C6H5CH2–H. 8. The BDEs in free radicals, ions, clusters, and complexes are collected in this volume. The listed order is as follows: the BDEs in neutrals (including free radicals), the BDEs in cations, and the BDEs in anions. For example, K Fe(CO)x–CO bonds are first; FeðCOÞC x –CO, second; then FeðCOÞx –CO bond. C NH 3 –NH 3 bond is first; (NH 3)H (NH 3) x –NH 3 bonds, second; then (NH2)K(NH3)x–NH3 bonds. CC(C)x–C bonds are first, then CK(C)x–C bonds, there xZ0, 1, 2, 3, etc. The book’s contents and the two indexes (species classes and compound names) may provide a method for quicker searching.

1.7

How to use the BDE data tables

All BDE data are filed into 225 separated tables. The C–H BDE in methane provides an example of how to find the BDEs.

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Comprehensive Handbook of Chemical Bond Energies

BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated

references in parentheses)

atom) DfH0 (R), kcal/mol (kJ/mol)

kcal/mol

Methane CH3–H

kJ/mol

Methods (references in parentheses)

References

(1) 105.0G0.1

439.3G0.4

(1) VLPP

(1) 1987DOB/BEN

(2) 105.3G0.7

440.6G2.9

(2) PIMS detection

(2) 1988RUS/SEE(b)

(3) 104.8G0.2

438.5G0.8

(3) Spectrometric

(3) 1990SEE/RUS

detection DfH0(R)Z35.06G0.1

(4) 105.3G0.6

440.6G2.5

(146.7G0.3)

(4) Resonance

(4) 1991NIC/DIJ

fluorescence detection (5) 104.99G0.03

439.28G0.13

(5) AE, revised

(5) 1999RUS/LIT

The first column in this table shows the broken bonds. The boldface emphasizes the dissociated atom or group; here, the H is boldfaced. For example, CH3CH2CH2CH3 shows a secondary C–H bond in n-butane is broken; (CH3CH2)3N shows a secondary C–H bond in triethylamine is broken. All expressions are similar. The heat of formation of free radicals is shown in this cell. Chapter 29 includes tables of all DfH0(R). The second column shows the experimental values of BDEs for the given bond. The numbers (1), (2), (3), (4), and (5) show five different resources or references. The recommended value is emphasized by boldface. The third column shows various experimental methods for the relevant BDE value. For an explanation of terms, see the Notations and Abbreviations list in this book. The fourth column shows the references for the given experimental methods and for the relevant BDE value. A maximum of five values are provided. This is sufficient for most users. Readers can search for more references while using the references here. The following provide three more examples:

BDEs (boldfaceZ recommended data; The broken bonds (boldfaceZdissociated group) Methoxybenzene or anisole

references in parentheses) kcal/mol

kJ/mol

Methods (references in parentheses)

References

(1) 64.8

271.1

(1) VLPP

(1) 1989SUR/KAF

(2) 65.2

272.8

(2) Tubular flow

(2) 1993ARE/LOU

reactor CH3–OC6H5

(3) 65.3

273.2

(3) VLPP

(3) 2001PRA/HEE

(4) 64.2G1.7

268.6G7.1

(4) Der. from

(4) 1986PED/NAY

DfH0 in ref.

a-Tocopherol

(1) 78.9

330.1

(1) EPR

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(1) 1992JAC/HOS

Introduction H

9

(2) 78.9

330.1

(2) EPR

(2) 1994LUC/PED

(3) 80.9G1, in

338.5G4.2

(3) AOP

(3) 1996BOR/LIU

(4) 79.3, in sol.

331.8

(4) PAC

(4) 1996WAY/LUS

(4) 77.3, in gas

323.4

(5) 78.23G0.25

327.31G1.05

(5) EPR

(5) 2003VAL/BRI

d-Tocopherol

(4) 82.2, in sol.

343.9

R5ZR7ZH

(4) 80.2, in gas

335.6

(6) 81.9

342.8

(6) Correlation

(6) 2000DEN/DEN

(6) 80.2

335.6

(6) 80.1

335.1

(1) 88.1

368.6

(1) AOP

(1) 1993BOR/ZHA

(2) 87.0

364.2

(2) Correlation

(2) 2000DEN/DEN

(1) 84.2

352.3

(2) 83.3

348.6

(4) 81.8

342.2

(2) 85.4

357.5

(3) 86.3, in sol.

361.1

(3) PAC

(3) 1997MAC/WAY

(3) 86.2, in gas

360.7

(4) 83.3

348.5

(4) EPR

(4) 2002PRA/DIL

p-tBu

(2) 85.8

358.8

p-N(CH3)2

(4) 79.5

332.6

R5

O

R7

CH2

O CH3

CH3

R

sol.

R = (CH2CH2CHCH2)3 H CH3 R5ZR7ZCH3 (Vitamin E)

b-Tocopherol R5ZCH3, R7ZH g-Tocopherol R5ZH, R7ZCH3

Diphenylamine, substituted

H N

Y YZp-Br p-MeO

p-Me

Y

1. The C–O BDE in methoxybenzen or anisole. The experimental data of BDE(C–O) are from four different methods. The first three values are contributed from independent measurements of different research groups. The last one is derived by Equation 1.2 where heats of formation of the parent molecules are taken from the given reference, and heats of formation of atoms and radicals are taken from Chapter 29. 2. The weakest H–O BDEs in four tocopherols (vitamin E). They emphasize the differences between experimental H–O BDEs in gas phase and liquid phase. 3. The H–N BDEs in substituted diphenylamine. They show the effects of various remote substitutes Y on the H–N BDEs.

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Comprehensive Handbook of Chemical Bond Energies

Similar arrangements are also for the BDEs in radicals, ions, and clusters from Chapter 11 through Chapter 28. Three examples are provided below: 1. The H-bond energies in water clusters. They are dimer, trimer, tetramer, pentamer, hexamer, heptamer, and octamer if xZ0, 1, 2, 3, 4, 5, 6, respectively. These show the H-bond energies significantly depend on the size of the clusters. 2. The FeC–C BDEs. Here L is the ligand and represents varied C-centered radicals, e.g., C, CH, CH2, CH3, and CF2. The FeC–C BDEs vary with the ligands. 3. The Co–C BDE in vitamin B12 family. The table presents five experimental values. 4. The BDEs of van der Waals complexes H2O(ice, surface)–X in the atmosphere; there X represents CO, HCl, O3, or CH4.

BDEs The broken bonds (boldfaceZdissociated fragment)

(boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(H3O)C(H2O)x–H2O xZ0

1

2

3

4

5

(1) 35.0G1.5

146G6

(1) HP MS

(1) 1986HIR/TAK

(2) 33.5

140.2

(2) Review

(2) 1992MEO

(3) 37.4G1.8

157G8

(3) GIM MS

(3) 1993HON/SUN

(4) 36.0

150.6

(4) HP MS

(4) 1997KEB/SEA

(5) 31.5G1.7

132G7

(5) GIB MS

(5) 2004HON/ARM

(6) MS

(6) 2003FRO/LOV(b)

(1) 20.2G1.5

85G6

(2) 20.8

87.0

(3) 22.2G0.8

93G3

(4) 22.3

93.3

(6) 20.9

87.4

(2) 17.4

72.8

(3) 17.9G0.5

74.9G2.1

(4) 17.0

71.1

(7) 17.9

74.9

(7) Review

(7) 1994HIR/YAM

(8) 17.4

72.8

(8) FT-ICR

(8) 1994THO/TON

(2) 12.3

51.5

(4) 15.3

64.0

(6) 12.8

53.6

(7) 12.7

53.1

(8) 13.9

58.2

(1) 11.8

49.4

(4) 13.0

54.4

(6) 12.2

51.0

(7) 11.6

48.5

(9) 10.5G0.6

43.9G2.5

(9) MS

(9) 2003WAN/TSA

(1) 10.7

44.8

(4) 11.7

49.0

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Introduction

6

11

(6) 10.6

44.4

(9) 9.4G0.9

39.3G3.8

(10) 12.0

50.3

(4) 10.3

43.1

(10) TOF MS

(10) 1993SHI/FOR

(6) 10.0

41.8

(9) 9.5G0.5

39.7G2.1

(10) 9.8

40.9

(11) 6.7

28.0

(11) CID

(11) 1991MAG/DAV

N

(12) w10.5

w44.0

(12) Extrapolate

(12) This volume

FeC–CH

(1) 101G7

423G29

(1) PD

(1) 1986HET/FRE

(1) 82G7

343G29

–CH2

–CH3

(2) 82.6G1.5

346G6

(2) GIB MS

(2) 1992SCH/ARM(b)

(3) 81.5G1

341G4

(3) Review

(3) 1996ARM/KIC

(1) 65G5

272G21

(3) 54.7G1.2

229G5

(4) !69

!289

(4) Ion reactions

(4) 1979ALL/RID

(5) 69G5

289G21

(5) Ion reactions

(5) 1984JAC/FRE(b)

(6) 57.1G2.3

239G10

(6) GIB MS

(6) 1989FIS/SCH

Co–C bonds

(1) 26G2

108.8G8.4

(1) Kinetics

(1) 1984HAL/KIM

B12-Ado; AdoZ5 0 -

(2) 30G2

125.5G8.4

(2) Kinetics

(2) 1986HAY/FIN

deoxyadenosyl,

(3) 34.5G1.8

144.3G7.5

(3) Kinetics

(3) 1987HAY/FIN

B12Zcobinamide

(4) 29.6G1.5

123.8G6.3

(4) Kinetics

(4) 1997CHE/YAN

(5) 31.3G2.9

131G12

(5) PAC

(5) 1998LI/LUO

(1) w2.4

w10

(1) FT-IR

(1) 1998ALL/VER

(2) 2.5G0.05

10.4G0.2

(2) IR

(2) 2000MAN/ROU

(3) R8.3

R34.7

(3) Mol. beam

(3) 2000AND/NAG

(4) 5.7G0.5

24G2

(4) Mol. beam

(4) 2005LOH/DAY

–O3

(5) 4.8

20

(5) FT-IR

(5) 2001BOR/CHI

–CO2

(6) 6.2

25.9

(6) Review

(6) 1991ELL/TUR

(7) 5.1G0.5

21.2G1.9

(7) TR mol. beam

(7) 2004AND/NAG

(1) 11.2

46.9

(1) NMR

(1) 1987MIZ/HAN

(2) 13.9G0.2

58.2G0.8

(2) TPD

(2) 2003SMI/LIV

(3) 12.0G1.4

50.2G5.9

(3) Kinetics

(3) 2006PRA/BER

–H18 2 O

(2) 13.8G0.2

57.7G0.8

–D2O

(2) 14.8G0.4

61.9G1.7

H2O(ice, surf.)–CO –HCl

H2O(ice, surf.)–H2O

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chapter two

Experimental methods for measuring BDEs 2.1

A summary of main experimental methods

The object of most end-users is to find reliable data. However, it is very helpful if the users know experimental BDE data’s sources. A very concise description of experimental methods is summarized in Table 2.1. It provides main methods, measured quantities, applications, and references. This description should aid the reader’s interpretation of the BDE data tables found throughout this handbook. Table 2.1 A Summary of Main Experimental Methods for Measuring BDEs Experimental Methods

Measured Quantities

Applications

Spectrometry

Spacing of vibrational energy levels

Diatomic molecules in gas phase

Pyrolysis kinetics, including † Toluene carrier tech † Very low pressure pyrolysis (VLPP)

Concentration of atoms, free radicals Species in gas and molecules vs. time at different and solution temperatures, using various phase detecting techniques, such as GC, HPLC, MS, FT–IR, UV/VIS, EPR, NMR, resonance fluorescence, chemiluminescence, and so on

References (1) 1968GAY (2) 1970DAR (3) 1979HUB/HER

1950SZW

(1) 1973GOL/SPO (2) 1979ROS/KIN (3) 1982MCM/GOL

† Shock tubes

(1) 1992DOU/MAC (2) 1997KIE/ZHA

†

Single-pulse shock tubes (SPST)

(1) 1981TSA (2) 1999TSA

†

Laser-powered pyrolysis

(1) 1982MCM/LEW (2) 1984LEW/GOL

(continued)

13

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Comprehensive Handbook of Chemical Bond Energies

Table 2.1 (continued) A Summary of Main Experimental Methods for Measuring BDEs Experimental Methods

Measured Quantities

Applications

References

Chemical equilibrium & kinetics

Concentration of atoms, free radicals Species in gas and solution and molecules at one or several phase temperatures, using various detecting methods

(1) 1966KER (2) 1977KER (3) 1982CAS/GRI (4) 1982MCM/GOL (5) 1984PAC/WIL (6) 1990KOE/SCO (7) 1990HAL (8) 1992WAL (9) 1994BER/ELL

Photolysis, including

Correlation between BDEs and rate constants or activation energies

(1) 1966KER (2) 1978KAT/RAJ (3) 2000DEN/DEN

† UV

Concentration at one or several temperatures, using various analytical methods

Species in gas phase

(1) 1971LAU/OKA (2) 1995BOY/NOZ

† Radiolysis

(1) 1990LIN/SHE (2) 2001DAS

† Laser

(1) 1987CHU/FOL (2) 1988PEN/CAO (3) 1997BEC/CAR

† Photosensitized

1967LOU/LAI

† Time-resolved photodissociation (TRPD)

1996DUN

Mass spectrometry (MS), including

† Electron impact (EI)

Measure the given quantities and describe their correlation with BDEs

Species in gas phase

Ion intensities vs. electron energy

(1) 2001ERV (2) 2001GRO (3) 2002SAB/FUJ (4) 2003OPE/RAB (1) 1979BER (2) 1984HOL/LOS (3) 1992HOL

† Guided ion beam (GIB) Ion intensities vs. ion kinetic energy

(1) 1995ARM (2) 1998DET/ERV (3) 2003ARM(b)

† High pressure (HPMS)

(1) 1994BUS/KEM (2) 1994BOW (3) 1999MCM

Ion intensities vs. temperature

† Ion cyclotron resonance Ion intensities, vs. time, vs. electron, (ICR) or photon energy

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(1) 1980DEF/MCI (2) 2000BOR/ING (3) 1999ABB/NOT

Experimental Methods for Measuring BDEs

† High temperature

15

Ion intensities vs. temperature

1984MAR

† Photoionization (PIMS) Ion intensities vs. photon energy

(1) 1994BER/ELL (2) 1994BAR

† Pulsed high pressure

Ion intensities at one or several temperatures

(1) 1989MEO (2) 1993SHA/KEB

† Kinetic method

Ion intensities

1994COO/PAT

† Kinetic energy release distributions

Ion intensities vs. product kinetic energy

1992BEA

† Threshold ionization

Ion intensities below a selected ionization threshold

(1) 2002BRA/MEH (2) 2002BRA/NEU

Photospectrometry, including Measure the given quantities and describe their correlation with BDEs

Species in gas phase

(1) 1999WEN/LIN (2) 2000NG (3) 2001ERV

† Photoelectron (PES)

Electron count vs. electron kinetic energy

(1) 1984MEA (2) 1994BER/ELL

† Electron photodetachment

Ion intensities vs. photon energy

(1) 1987WET/BRA (2) 1989CHE/ALB

† Flowing afterglow (FA) Ion intensities, vs. time, or vs. ion kinetic energy

(1) 1992SQU (2) 1994BER/ELL

† Collision-induced dissociation (CID)

Collision energy vs. cross section

(1) 1994WEN/SQU (2) 2001HAM/WEN (3) 2003ARM(B)

† Photoionization MS (PIMS)

Ions are detected by MS

1994BER/ELL

† TPEPICO

Threshold photoelectron photoion coincidence

2005LAR/KER

Electrochemical, including †

Acidity, reversible redox potentials

Species in solution

(1) 1993BOR/ZHA (2) 1993WAY/PAR (3) 1993ARN/FLO (4) 1995BOR/SAT

Amplitude of photoacoustic signal and solution transmittance

Species in solution

(1) 1989KAM/GIL (2) 1994PET (3) 1999LAA/MUL (4) 1999SAN/LAG (5) 2002SAN/MUR (6) 2003GIT/JIA

Acidities and oxidation potentials (AOP)

Photoacoustic calorimetry (PAC)

† Time-resolved PAC † Laser-induced photoacoustic calorimetry (LIPAC) † Laser-induced timeresolved photoacoustic calorimetry

(7) 2003CHE/LI

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 2.1 (continued) A Summary of Main Experimental Methods for Measuring BDEs Experimental Methods

Measured Quantities

Calorimetry † Microcalorimetrc

Applications

Heats of combustion, vaporization, and formation

Species in solid, solution, or gas–solid surface

References

(1) 1995LEB/CHI (2) 2004SIL/MAT

† Solution titration

Reaction heats

(3) 1992BUR (3) 1992HOF (4) 1995NOL

† Gas–solid surface

Femtomole adsorption heats on single-crystal surface

(5) 1998BRO/KOS (6) 1998CER

Thermal desorption spectroscopy (TDS)

An adsorbed surface is heated and desorbing species are detected with MS, IR or others

Gas–solid interface

(1) 1986WOO/DEL (2) 1990JON/NIE

Monoenergetic beam of helium atoms are scattered from ordered surfaces and detected

Gas–solid interface

1996HOF/TOE

Temperature programmeddesorption (TPD)

Helium atom scattering (HAS)

The readers may find more methods for determining the BDEs in e-publication (2002SIL).

2.2

The conversion between D0, De, and DH0

Related energies are often encountered when searching for experimental BDE data. D0 the bond dissociation energy at 0 K De the electronic energy, i.e., the minimum on the potential energy curve or surface or the well depth. D0(RKX) may be determined from De, as shown in figure: Energy 0

Dissociated fragments (R + X) at 298 K Enthalpy change from 0 to 298 K distance

ro DH

o

Do Associated species RX at 298 K Enthalpy change from 0 to 298 K Associated species RX at 0 K Zero point energy De

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Experimental Methods for Measuring BDEs

D0 Z De KDðZPEÞ

17

(2.1)

Here D(ZPE) is the change of the zero point vibrational energies in the species involved in the bond dissociation processes, the dissociating state as the energy reference. For diatomic molecules and Morse potential, the approximate relationship follows: D0 x

u2e u ux K eC e e 4ue xe 2 4

u2e 4ue xe u ux DðZPEÞ Z e K e e 2 4 De x

(2.2)

Here ue and xe are the spectroscopic parameters. In general, the relationship between the dissociation enthalpy change and temperature must be determined to make the conversion from D0 to DH0. There are four methods for this conversion. 1. Thermochemical calculations (2005RUS/BOG). 2. Calculations by quantum chemistry (1997CUR/RAG; 2000CIO/SCH; 2002NIST/COM). 3. Using NIST-JANAF Thermochemical Tables (1998CHA). 4. Simple approximation. This is good for biatomic, triatomic, and tetraatomic species. This method is reviewed below.

2.2.1

Diatomic molecules

From thermodynamics, the enthalpy change, DH, and internal energy change, DE, for the bond dissociation processes is described as DH Z DE C DðPVÞ

(2.3)

Where D(PV) is the molar work that is equal to D(RT), assuming 1 molar ideal gas. For diatomic species, a vibrational free degree becomes a translational one because of the bond dissociation. An approximate equation is obtained as 3 DH Z DE C RT zD0 C RT 2

(2.4)

For TZ298.15 K, the BDE is derived based on the experimental D0 at 0 K 3 BDE h DH0 zD0 C RT 2

(2.5)

Z D0 C 0:8886 kcal=mol Z D0 C 3:7181 kJ=mol Here the R is the gas constant; the H in the nomenclature DH0 emphasizes that the BDE is the enthalpy change of the dissociation processes. The superscript ‘0’ denotes the standard conditions of thermodynamics.

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Comprehensive Handbook of Chemical Bond Energies

2.2.2

Polyatomic molecules

For the bond dissociation process of polyatomic molecules at the standard conditions of thermodynamics RKX/ R C X The formation heat for each species at TZ298.15, K is estimated Df H0 Z E0 C ZPE C ðEtrans C Erot C Evib Þ C RT

(2.6)

where E0 is the internal energy, Etrans, Erot, and Evib are the translational, rotational, and vibrational contribution to the enthalpy, respectively. According to the definition of the BDE DH0 Z Df H0 ðRÞ C Df H0 ðXÞKDf H0 ðRXÞ

(2.7)

Z De KDðZPEÞ C DEth C RT or where

DH0 Z D0 C DEth C RT

(2.8)

De Z DE0 Z E0 ðRÞ C E0 ðXÞKE0 ðRXÞ

(2.9)

DðZPEÞ Z ZPEðRÞ C ZPEðXÞKZPEðRXÞ

(2.10)

DE0 represents the internal energy change of the dissociation reactions. DEth is the change associated with the traslational, rotational, and vibrational energy in going from TZ0 to 298.15 K. The following is this general result: D Eth R

N RT 2

(2.11)

Here N is the increasing number of translation and rotational degrees of freedom because of the dissociation reactions. NZ1 for diatomic species; NZ2 for non-linear triatomic ones (as H–OH); and NZ3 for non-linear tetraatomic ones (as H–NH2). Therefore, there is a simple relationship DH0 % D0 C

N C 1 RT 2

(2.12)

For diatomic molecules, the D(ZPE) and DEth become the simplest and are given by 1 1 DðZPEÞ z ue Z hn 2 2 DEth Z

3 3 3 1 RT C RT K RT C RT Z RT 2 2 2 2

(2.13) (2.14)

Here h is the Plank constant, and n is the vibrational frequency. Finally, Equation 2.5 is reproduced.

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chapter three

BDEs of C–H bonds 3.1

Chain saturated hydrocarbons

Table 3.1 C–H BDEs in Chain Saturated Hydrocarbons BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Methane

(1) 105.0G0.1

439.3 G0.4

(1) VLPP

(1) 1987DOB/BEN

CH3–H

(2) 105.3G0.7

440.6G2.9

(2) PIMS detect.

(2) 1988RUS/SEE(b)

DfH0(R)Z35.06G0.1

(3) 104.8G0.2

438.5G0.8

(3) Spectro. detec.

(3) 1990SEE/RUS

(4) 105.3G0.6

440.6G2.5

(4) RF detect.

(4) 1991NIC/DIJ

(5) 104.99G0.03 439.28G0.13

(5) AE, revised

(5) 1999RUS/LIT

CH3–D CD3–D

106.0G1 107.3G1

443.5G4.2 448.9G4.2

Review

1974GUR/KAR

(146.7G0.3)

Methane, deuteride or tritide

CT3–D

106.6G1

446.0G4.2

CH3–T

106.8G1

446.9G4.2

CD3–T

107.8G1

451.0G4.2

CT3–T

106.4G2

445.2G8.4

Ethane

(1) 100.5G0.5

420.5G2.1

(1) Kinetics

(1) 1984PAC/WIN

CH3CH2–H DfH0(R)Z28.4G0.3

(2) 100.5G0.5 (3) 100.8G0.7

420.5G2.1 421.7G2.9

(2) RF detect. (3) PIMS detect.

(2) 1986BRO/LIG (3) 1988RUS/SEE(b)

(4) 101.0G0.4

422.6G1.7

(4) PIMS detect.

(4) 1992SEA/PIL

(5) 100.5G0.3

420.5G1.3

(5) VLPP

(5) 1997DOB/BEN

(118.8G1.3)

(continued)

19

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Table 3.1 (continued) C–H BDEs in Chain Saturated Hydrocarbons

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Propane

(1) 99.9G1.0

418.0G4.2

(1) Radical buffer

(1) 1982CAS/GRI

CH3CH2CH3

(2) 99.8G2

417.6G8.4

(2) AE

(2) 1992HOL

DfH0(R)Z23.8G0.5 (100G2)

(3) 100.9G0.5

422.2G2.1

(3) SPST

(3) 1996TSA

(4) 101.2G0.5

423.4G2.1

(4) PIMS detect.

(4) 1997SEE/SLA

Propane

(1) 98.1G0.7

410.5G2.9

(1) PIMS detect.

(1) 1988RUS/SEE(b)

CH3CH2CH3

(2) 98.9G0.6

413.8G2.5

(2) PIMS detect.

(2) 1990SEE/RUS

DfH0(R)Z21.0G0.7 (88G3)

(3) 98.6G0.4

412.5G1.7

(3) PIMS detect.

(3) 1992SEA/PIL

(4) 97.8G0.5

409.2G2.1

(4) PIMS detect.

(4) 1997SEE/SLA

(5) 97.4G1.0

407.5G4.2

(5) SPST

(5) 1999TSA

Butane CH3CH2CH2CH3

(1) 101G2 (2) 100.2

422.6G8.4 419.2

(1) EI (2) AE

(1) 1958COT (2) 1988HOL/LOS

DfH0(R)Z18.6G0.5 (77.8G2.1)

(3) 100.7

421.3

(3) SPST

(3) 1990WAL/TSA

(4) 101.7G0.5

425.5G2.1

(4) PIMS detect.

(4) 1997SEE/SLA

(1) 1990SEE/RUS

Butane

(1) 99.1G0.4

414.6G1.7

(1) PIMS detect.

CH3CH2CH2CH3

(2) 98.3G0.5

411.1G2.2

(2) RF detect.

(2) 1992SEA/PIL

DfH0(R)Z16.2G0.5 (67.8G2.1)

(3) 98.6G0.5

412.5G2.1

(3) Review

(3) 1996TSA

(4) 98.3G0.5 (5) 97.4G1.0

411.3G2.1 407.5G4.2

(4) PIMS (5) SPST

(4) 1997SEE/SLA (5) 1999TSA

iso-Butane

(1) 100.2G1

419.2G4.2

(1) Exp. analysis

(1) 1976BEN

(CH3)2CHCH3

(2) 99.3G2

415.5G8.4

(2) AE

(2) 1992HOL

DfH0(R)Z16.7G1.0 (70G4)

iso-Butane (CH3)3C–H DfH0(R)Z11.5G0.7 (48G3)

(3) 101.6G0.5

425.1G2.1

(3) PIMS detect.

(3) 1997SEE/SLA

(4) 100.9G1

422.0G4.2

(4) SPST

(4) 1999TSA

(1) 95.6G0.7 (2) 95.0

400.0G2.9 397.5

(1) SPST (2) VLPP

(1) 1985TSA (2) 1987BEN/KON

(3) 95.5G0.7

399.6G2.9

(3) RF detect.

(3) 1991SEA/PIL

(4) 95.5G0.3

399.6G1.3

(4) RF detect.

(4) 1992SEA/PIL

(5) 95.7G0.7

400.4G2.9

(5) RF detect.

(5) 1996TSA

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BDEs of C–H Bonds

Pentane

21

100.2

419.2

Derived from

1986PED/NAY

DfH0 in ref.

nC5H11–H DfH0(R)Z13(54.4)

Neo-pentane

(1) 99.4G1

415.9G4.2

(1) Polanyi plot

(1) 1966KER

(CH3)3C(CH3) DfH0(R)Z8.7G2 (36.4G8.2)

(2) 100.3G1 (3) 99.4G1

419.7G4.2 415.9G4.2

(2) Kinetics (3) SPST

(2) 1969LAR/HAR (3) 1969TSA

Pentane

(4) 101G2

422.6G8.4

(4) Review

(4) 1982MCM/GOL

(5) 101.1

423

(5) LP

(5) 2001IMR/DOB

99.2

415.1

Derived from

1986PED/NAY

DfH0 in ref.

CH3CH2(CH2)2CH3 DfH0(R)Z12 (50.2)

Pentane

99.1

414.5

Correlation

2005DEN/TUM

2-Methylbutane

(1) 91.6G2

383.3G8.4

(1) SPST

(1) 1969TSA

(CH3CH2)CH(CH3)2

(2) 96.5G1

403.8G4.2

(2) SPST

(2) 1981TSA

DfH0(R)Z7 (29)

(3) 92.6

387.4

(3) PES

(3) 1986KRU/BEA

(4) 95.8

400.8

(4) SPST

(4) 1999TSA

(5) 96.1

402.0

(5) Correlation

(5) 2005DEN/TUM

99.0

414.2

Derived from

1986PED/NAY

CH3CH2CH2CH2CH3

Hexane

DfH0 in ref.

CH3(CH2)4CH3 DfH0(R)Z8 (33.5)

Hexane

98.0

410.0

Derived from

1986PED/NAY

DfH0 in ref.

CH3CH2(CH2)3CH3 DfH0(R)Z7(29.3)

Hexane

99.1

414.5

Correlation

2005DEN/TUM

CH3CH2CH2CH2CH2CH3

(continued)

7366—CHAPTER 3—6/2/2007—13:01—JEBA—15359—XML MODEL B – pp. 19–145

22

Comprehensive Handbook of Chemical Bond Energies

Table 3.1 (continued) C–H BDEs in Chain Saturated Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) 2,2,Dimethylbutane

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

98.0

410.2

Correlation

2005DEN/TUM

(1) 94.7G2 (2) 95.4

396.2G8.4 399.3

(1) Pyrolysis (2) Correlation

(1) 1983SER/GOR (2) 2005DEN/TUM

2,3-Dimethylbutane

(1) 95.4G3.1

399.2G13.0

(1) Equilibrium

(1) 2000KIR/KOR

(iso-C3H7)CH(CH3)2

(2) 94.7

396.4

(2) Correlation

(2) 2005DEN/TUM

3-Methylpentane (CH3)CH(C2H5)2

95.5

399.7

Correlation

2005DEN/TUM

Heptane

98.0

410.0

Derived from

1986PED/NAY

(CH3)3CCH2CH3

2-Methylpentane (n-C3H7)CH(CH3)2 DfH0(R)Z0.8G2 (3.3G8.2)

DfH0(R)Z0.7G2.4(3.1G10)

DfH0 in ref.

CH3CH2(CH2)4CH3 DfH0(R)Z2(8.2)

Heptane

99.1

414.5

Correlation

2005DEN/TUM

99.4

415.7

Correlation

2005DEN/TUM

94.9

397.1

Correlation

2005DEN/TUM

CH3CH2CH2(CH2)3CH3

Heptane CH3(CH2)2CH2(CH2)2CH3

3-Methylhexane (CH3)CH(C2H5)(C3H7)

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BDEs of C–H Bonds

2,4-Dimethylpentane

23

95.6

400.0

Correlation

2005DEN/TUM

95.5

399.6

Correlation

2005DEN/TUM

99.1

414.5

Correlation

2005DEN/TUM

99.4

415.7

Correlation

2005DEN/TUM

95.6

400.0

Correlation

2005DEN/TUM

96.7

405.4

Correlation

2005DEN/TUM

2,5-Dimethylhexane (CH3)2CHCH2CH2CH(CH3)2

95.6

400.0

Correlation

2005DEN/TUM

3-Methyloctane

94.8

396.6

Correlation

2005DEN/TUM

95.4

399.1

Correlation

2005DEN/TUM

(CH3)2CHCH2CH(CH3)2

2,2,Dimethylpentane (CH3)3CCH(CH3)2

Octane CH3(CH2)4CH2CH2CH3

Octane CH3(CH2)3CH2(CH2)2CH3

2,2,4-Trimethylpentane (CH3)2CHCH2C(CH3)3

2,3-Dimethylhexane (CH3)2CHCH(CH3)(C3H7)

(CH3)CH(C2H5)(n-C5H11)

2,2,5-Trimethylhexane (CH3)3C(CH2)2CH(CH3)2

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24

Comprehensive Handbook of Chemical Bond Energies

3.2

Chain unsaturated hydrocarbons

Table 3.2 C–H BDEs in Chain Unsaturated Hydrocarbons BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) Acetylene HCbC–H DfH0(R)Z135.6G0.2 (567.4G0.8)

Acetylene, substituted X–CbC–H

recommended data; reference in parentheses) kcal/mol (1) 134.9G1.2

kJ/mol 564.4G5.0

Methods (reference in parentheses) (1) AE

References (1) 1979BER

(2) 132.9G0.7

556.1G2.9

(2) PEDt

(2) 1990ERV/GRO

(3) 133.1G0.7

556.9G2.9

(3) GPA

(3) 1994BER/ELL

(3) 132.8G0.7 556.6G2.9 (4) 133.32G0.07 557.81G0.30

(3) Recommended (4) Photolysis (4) 1994MOR/ASH

(5) 131.3G0.7

549.4G2.9

(5) EA

(5) 2002KIR/TSC

(1) 130.2G3,

544.8G12.6

(1) PES

(1) 1995ROB/POL

(2) MS (3) GPA

(2) 1999HIL/POU (3) 2003REE/HAR

0K

XaCH3 DfH0(R)Z123G3.0 (515G13) BFK 3 Ph

(2) 130.8 (3) 133G5

547.3 556.5G21

C(O)OCH3

(3) 132G5

552.3G21

CC(O)N(CH3)2

(3) 132G5

552.3G21

128.8G2.9, 0 K

539G12

CID

2000SHI/ERV

(1) 89.2G2.4 (2) 87.2G2

373.2G10.0 364.8G8.4

(1) VLPP (2) AE

(1) 1979KIN/NGU (2) 1988HOL/LOS (3) 1995ROB/POL

Diacetylene HCbC–CbC–H

Propyne CHbCCH3 DfH0(R)Z81.0G1.0 (339G4)

(3) 90.3G3

377.8G12.6

(3) GPA

(4) 88.9G1.0

372.0G4.2

(4) Recommended (4) 1996TSA

(5) 91.8G1.0

384.1G4.2

(5) SPST

(5) 1999TSA

2-Butyne

(1) 90.7

379.5

(1) SPST

(1) 1978TSA

CH3CbCCH3

(2) 87.4G2

365.7G8.4

(2) VLPP

(2) 1982NGU/KIN

DfH0(R)Z72.8 (304.5)

(3) 84.8 (4) 91.3

354.7 382.0

(3) Correlation (4) Derived

(3) 2000DEN/DEN (4) 2004JAN/ROS

1-Butyne

(1) 85.0

355.6

(1) VLPP

(1) 1981NGU/KIN

HCbCCH2CH3

(2) 87.3

365.3

(2) SPST

(2) 1981TSA

DfH0(R)Z75.6 (316.5)

(3) 83.1G2.2

347.7G9.2

(3) Review

(3) 1982MCM/GOL

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BDEs of C–H Bonds

1-Penten-3-yne CH2aCHCbCCH3

25

(4) 82.9

346.8

(4) Correlation

(4) 2000DEN/DEN

(5) 89.1

373.0

(5) Derived

(5) 2004JAN/ROS

86.8

363.3

VLPP

1992STA/KIN

87.3G2.3

365.3G9.6

VLPP

1981KIN/NGU

83.6G2

349.8G8.4

AE

1976LOS/TRA

DfH0(R)Z84.0 (351.5)

2-Pentyne CH3CbCCH2CH3 DfH0(R)Z65.2G2.2 (272.8G9.2)

1-Pentyne HCbCCH2CH2CH3 DfH0(R)Z66.2G2.0 (277.0G8.4)

3-Methyl-1-butyne

(1) 82.5G2

345.2G8.4

(1) AE

(1) 1976LOS/TRA

HCbCCH(CH3)2

(2) 81.0G2.3

338.9G9.6

(2) VLPP

(2) 1977KIN

82.3G2.7

344.3G11.3

VLPP

1981KIN/NGU

5-Decyne CH3(CH2)3CbCCH2(CH2)2CH3

83.2

348.2

Correlation

2005DEN/TUM

Triacetylene

(1) 126.8G1.6

530.5G6.7

(1) GPA

(1) 1994NAT/KOC

HCbC–CbC–CbC–H

(2) w129.8G3

w543G13

(2) Re-evaluated

(2) 2001ERV

(1) 1981STE/ROW

DfH0(R)Z61.5G2.2 (257.3G9.2)

4-Methyl-2-pentyne CH3CbCCH(CH3)2 DfH0(R)Z53.0G2.2 (221.8G9.2)

Ethylene

(1) 110.1G2

460.7G8.4

(1) Kinetics

H2CaCH2

(2) 111.2G0.8

465.3G3.3

(2) Recommended (2) 1994BER/ELL

DfH0(R)Z71.6G0.8 (299.6G3.3)

(3) 110.2G0.4

461.1G1.3

(3) FT-IR-GC

(3) 1996KAI/WAL

(4) 110.7G0.6

463.0G2.7

(4) GPA, revised

(4) 2002ERV/DET

(5) 110.9G0.6

464.2G2.5

(5) TPEPICO

(5) 2005LAG/BAE

(continued)

7366—CHAPTER 3—6/2/2007—13:02—JEBA—15359—XML MODEL B – pp. 19–145

26

Comprehensive Handbook of Chemical Bond Energies

Table 3.2 (continued) C–H BDEs in Chain Unsaturated Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Allene

(1) 92.4G1.2

386.6G5.0

(1) Kinetics

(1) 1971WAL

CH2aCaCH2

(2) 88.7G3

371.1G12.6

(2) GPA

(2) 1995ROB/POL

SPST

(1) 1988CUI/HE

DfH0(R)Z81.0G1 (338.9G4)

Propene

(1) 109G2.4

456.1G10.0

CH3CHaCH2

(2) 111.1

464.8

(2) 1999TSA

DfH0(R)Z63.8G1.5 (266.9G6)

Propene

(1) 87.2G0.5

364.8G2.1

(1) PST

(1) 1991ROT/BAU

CH2aCHCH3

(2) 88.8G0.4

371.5G1.7

(2) GPA

(2) 1996ELL/DAV

DfH0(R)Z40.8G0.7 (171G3)

1,3-Bytadiene

(3) 88.2G0.7

369G3

(3) Recommended (3) 1996TSA

(4) 88.8G0.4 (5) 87.0G1.1

371.5G1.7 364.0G4.6

(4) PES (5) PIMS detect.

(4) 1996WEN/POL (5) 1997SEE/SLA

114.4

478.8

Derived

2004JAN/ROS

102.2

427.7

Derived

2004JAN/ROS

89.9

376.3

Derived

2004JAN/ROS

CH2aCHCHaCH2 DfH0(R)Z87.1 (364.4)

1,3-Bytadiene CH2aCCHaCH2 DfH0(R)Z74.9 (313.3)

Buta-1,2-diene CH2aCaCHCH3

(Z)-2-Butene

(1) 89.7

375.3

(1) SPST

(1) 1999TSA

(Z)-CH3CHaCHCH3

(2) 85.0

355.8

(2) Correlation

(2) 2000DEN/DEN

85.3

356.8

Correlation

2000DEN/DEN

DfH0(R)Z34.9G2 (146G8)

(E)-2-Butene (E)-CH3CHaCHCH3

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BDEs of C–H Bonds

27

1-Butene

(1) 98.1

410.5

(1) PES

(1) 1984SCH/HOU

CH2aCH–CH2CH3

(2) 98.2

410.9

(2) Correlation

(2) 2005DEN/TUM

DfH0(R)Z46.0 (192.5)

1-Butene

(1) 82.3

344.3

(1) SPST

(1) 1969TSA

CH2aCH–CH2CH3

(2) 82.6G1.3

345.6G5.4

(2) Review

(2) 1982MCM/GOL

DfH0(R)Z32.5 (136.2)

iso-Butene CH2aC(CH3)(CH3) DfH0(R)Z33.0 (137.9)

(3) 83.8

350.6

(3) PA

(3) 1987LIA/AUS

(4) 83.5

349.2

(4) Correlation

(4) 2001TUM/DEN

(5) 85.6

358.2

(5) Derived

(5) 2004JAN/ROS

(1) 85G2 (2) 86.7G0.6

355.6G8.4 362.8G2.5

(1) MS (2) Shock tube

(1) 1977LIA/AUS (2) 1991ROT/BAU

(3) 88.3G2.3

369.4G9.6

(3) PES

(3) 1996WEN/POL

(4) 89.1

372.8

(4) SPST

(4) 1999TSA

(5) 89.9

376.3

(5) Derived

(5) 2004JAN/ROS

(1) 1973ONE/BEN

1,3-Pentadiene

(1) 79.8G1.0

333.9G4.2

(1) Iodination

CH2aCHCHaCHCH3

(2) 79.7G1.0

333.5G4.2

(2) Pyrolysis

(2) 1980TRE

DfH0(R)Z49G3 (205G12.6)

(3) 83G3

347.3G12.6

(3) Review

(3) 1982MCM/GOL

2,3-Pentadiene

87.2

365.0

Correlation

2000DEN/DEN

(1) 1970EGG/JOL

CH3CHaCaCHCH3

1,4-Pentadiene

(1) 79.5G1.7

332.6G7.1

(1) Isomerization

(CH2aCH)2CH2

(2) 76.4

319.7

(2) Pyrolysis

(2) 1982TRE

DfH0(R)Z49.7G1.0

(3) 76.6G1.0

320.5G4.2

(3) PAC

(3) 1991CLA/CUL

(207.9G4.2)

(3) 76.6G1.0

320.5G4.2

(3) AE

(4) 77.5 (5) 76.0

324.4 318.0

(4) Derived (5) Correlation

(4) 2004JAN/ROS (5) 2005DEN/TUM

1-Pentene

(1) 82.5G2

345.2G8.4

(1) AE

(1) 1976LOS/TRA

CH2aCHCH2CH2CH3

(2) 83.4

348.8

(2) Correlation

(2) 2000DEN/DEN

83.0

347.2

Correlation

2000DEN/DEN

DfH0(R)Z26.2G2 (109.6G8.4)

2-Methyl-1-butene CH2aC(CH3)CH2CH3

(continued)

7366—CHAPTER 3—6/2/2007—13:03—JEBA—15359—XML MODEL B – pp. 19–145

28

Comprehensive Handbook of Chemical Bond Energies

Table 3.2 (continued) C–H BDEs in Chain Unsaturated Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

3-Methyl-1-butene

(1) 79.5G1.7

332.6G7.1

(1) Isomerization

CH2aCHCH(CH3)2

(2) 76.4

319.7

(2) Pyrolysis

(2) 1982TRE

DfH0(R)Z20.8G2

(3) 83.1

347.7

(3) Re-anal.

(3) 1998BRO/BEC

(4) 81.2

339.7

(4) Correlation

(4) 2000DEN/DEN

100.9

422.1

Correlation

2005DEN/TUM

84.2

352.4

Correlation

2000DEN/DEN

(1) 85.1G2 (2) 87.9

356.1G8.4 367.7

(1) AE (2) Correlation

(1) 1976LOS/TRA (2) 2005DEN/TUM

87.2

365.0

Correlation

2005DEN/TUM

(1) 81.7G1.5

341.8G6.3

(1) Derived from

(1) 1986PED/NAY

(2) 82.2

344.0

DfH0 in ref. (2) Correlation

(2) 2005DEN/TUM

(1) 80.6G1.5

337.2

(1) Derived from

(1) 1986PED/NAY

(87.0G8.4)

3-Methyl-1-butene

(1) 1970EGG/JOL

CH2aCHCH(CH3)2

3-Methyl-2-butene CH3CHaC(CH3)2

2-Ethyl-1-propene CH2aC(CH2CH3)CH3 DfH0(R)Z26.2G2.0 (109.6G8.4)

Penta-2,3-diene CH3CHaCaCHCH3

(E)-2-Pentene (E)-CH3CHaCHCH2CH3

(Z)-2-Pentene

DfH0 in ref.

(Z)-CH3CHaCHCH2CH3

1-Hexene

(2) 82.7

346.2

(2) Correlation

(2) 2005DEN/TUM

83.4

348.8

Correlation

2001TUM/DEN

89.6G3.1

374.9G13.0

Derived

2005FAT/KAS

CH2aCHCH(CH2)2CH3

2,3-Dimethyl-1,3-butadiene CH2aC(CH3)C(CH3)aCH2

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BDEs of C–H Bonds

29

3-Methyl-1,4-pentadiene

(1) 76.6G1.0

320.5G4.2

(CH2aCH)2CH(CH3)

(2) 77

322.2

PAC

(1) 1991CLA/CUL (2) 1999LAA/MUL

DfH0(R)Z46.3 (202.0)

2,3-Dimethyl-2-butene

(1) 78.0G1.0

326.4G4.2

(1) Iodination

(1) 1973ROD/WU

(CH3)2CaC(CH3)2

(2) 84.3

352.8

(2) Correlation

(2) 2005DEN/TUM

79.3

332.0

Correlation

2001TUM/DEN

79.8

333.9

Correlation

2001TUM/DEN

DfH0(R)Z9.5G1.5 (39.7G6.3)

4-Methyl-3-pentene (CH3)2CaCHCH2CH3

(Z)-4-Methyl-2-pentene (Z)-(CH3)2CHCHaCHCH3

2,3-Dimethyl-1-butene

(1) 76.3G1.0

319.2G4.2

(1) Iodination

(1) 1973ROD/WU

CH2aC(CH3)CH(CH3)2

(2) 83.9

351.1

(2) Correlation

(2) 2005DEN/TUM

79.3

332.0

Correlation

2001TUM/DEN

83.4

348.9

Correlation

2000DEN/DEN

81.9

342.7

Correlation

2000DEN/DEN

80.3

336.1

Correlation

2001TUM/DEN

83.6

349.8

Correlation

2005DEN/TUM

DfH0(R)Z9G1.5 (37.7G6.3)

1,3-Octediene CH2aCHCHaCHCH2(CH2)2CH3

1-Octene CH2aCHCH2(CH2)4CH3

(E)-2-Octene (E)-CH3CHaCHCH2(CH2)3CH3

(Z)-2,5-Dimethyl-3-hexene (Z)-(CH3)2CHCHaCHCH(CH3)2

Nona-1,8-diene CH2aCHCH2(CH2)4CHaCH2

(continued)

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30

Comprehensive Handbook of Chemical Bond Energies

Table 3.2 (continued) C–H BDEs in Chain Unsaturated Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) (Z)-Non-2-ene

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

82.2

344.0

Correlation

2005DEN/TUM

E,E-Deca-2,7-diene CH3CHCHCH2(CH2)3CHCHCH3

81.6

341.6

Correlation

2005DEN/TUM

Z,Z-2,8-Decediene

81.6

341.6

Correlation

2001TUM/DEN

83.4

348.8

Correlation

2001TUM/DEN

85.9

359.4

AOP

1996ZHA/FRY

81.0

338.9

AOP

1996ZHA/FRY

(Z)-CH3CHaCHCH2(CH2)4CH3

CH3CHaCH(CH2)4CHaCHCH3

1-Hexadecene CH2aCHCH2(CH2)12CH3

Allyl triphenyl, phosphonium bromide Ph3PCCH2CHaCH2 BrK

3-Phenyl-allyl triphenyl phosphonium, bromide Ph3PCCH2CHaCHPh BrK

7366—CHAPTER 3—6/2/2007—13:03—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

3.3

31

Cyclic hydrocarbons

Table 3.3 C–H BDEs in Cyclic Hydrocarbons BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Cyclo-propene

H

2

H 3

1

H

H C–H at 1 site DfH0(R)Z105.1G4.1 (439.7G17.2) C–H at 3

Cyclo-propane

H H

(1) 103G3

431.0G12.6

(1) GPA

(1) 2002KAS/BRO

(2) 90.4G4 (3) 91.1

378.3G12.6 381.1

(2) ICR (3) Correlation

(2) 1980DEF/MCI (3) 2005DEN/TUM

(1) 101G3

422.6G12.6

(1) Polanyi plot

(1) 1966KER

(2) 100.2G0.4

419.3G1.7

(2) Kinetics

(2) 1978APP/KLU

(3) 106.3G0.25

444.8G1.0

(3) VLPP

(3) 1979BAG/BEN

(4) 105.9G2.7

443.1G11.3

(4) ICR

(4) 1980DEF/MCI

429.0

(5) Correlation

(5) 2001TUM/DEN

97.4G1.6

407.5G6.7

Iodination

1971MCM/GOL

106.7G3.7

446.4G15.5

GPA

2003FAT/MCC

DfH0(R)Z66.9G0.3 (279.9G1.3) (5) 102.5

Methyl-cyclo-propane

CH2

H

DfH0(R)Z51.1G1.6 (213.8G6.7)

3,3-Dimethyl-cyclo-propene

H

2 1

H

CH3 3 CH3

(continued)

7366—CHAPTER 3—6/2/2007—13:04—JEBA—15359—XML MODEL B – pp. 19–145

32

Comprehensive Handbook of Chemical Bond Energies

Table 3.3 (continued) C–H BDEs in Cyclic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 95G3

397.5G12.6

(1) Polanyi plot

(1) 1966KER

(2) 96.5

403.8

(2) Polanyi plot

(2) 1971FER/WHI

(3) 96.8G1.0

405.0G4.2

(3) Iodination

(3) 1972MCM/GOL

(4) 97.8G0.3 DfH0(R)Z52.4G1.0 (219.2G4.2) (5) 100.0

409.2G1.3 418.5

(4) Kinetics (5) Correlation

(4) 1978APP/KLU (5) 2001TUM/DEN

79.3G3.1

331.8G13.0

Derived

2005FAT/KAS

85.6G2.6

358.2G10.9

FT-MS

2005FAT/LIS

76G4.2

318.0G17.6

FT-MS

2005FAT/LIS

84.5

353.5

AOP

1989BOR/HAR

86.5G2

361.9G8.4

VLPP

1981STE

Cyclo-butane

H H

1,3-Dimethylene-cyclo-butane

H H

1-Phenyl-cyclo-butene

H

C6H5

1-Phenyl-cyclo-buten-3-yl

H

C6H5

6,6-Dimethylfulvene

Me

CH2

6

H

1 5 2 4 3

1,3-cyclo-Pentadienes, substituted

CH2

H

7366—CHAPTER 3—6/2/2007—13:04—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

33

1,3-cyclo-Pentadiene, substituted

H 1 5 2 4 3 at 1 site H

(1) 82.9G2.2

346.9G9.2

(1) ICR

(2) 81.2

339.7

(2) AOP

(2) 1988BOR/CHE

(3) 83.9G0.5

351.0G2.1

(3) Electrochemical

(3) 1991PAR/HAN

(4) 82.5G1

345.2G4.2

(4) RST

(4) 2001ROY/BRA

358G7

(5) TR-PAC

(5) 2006NUN/AGA

313.8

(6) AOP

(6) 1991BOR/CHE

(1) 77

322.2

(1) AOP

(1) 1989BOR/HAR

(1) 78

326.4

(2) 74.1

310.0

(2) Pyrolysis

(2) 1995ROT/HUN

DfH0(R)Z65.5G1.7 (274.1G7.3) (5) 85.6G1.7 (6) 75

at 1,4 site Ph2

(1) 1980DEF/MCI

1,3-cyclo-Pentadienes, substituted

R R

H R

R

R

RZMe DfH0(pentamethyl-cyclopentadienyl)Z16.1G1.0 (67.4G4.2) Ph

Cyclo-pentene

H H

(1) 82.3G1

344.3G4.2

(1) Iodination

(1) 1970FUR/GOL(b)

(2) 82G2

343.1G8.4

(2) AE

(2) 1976LOS/TRA

(3) 81.9

342.5

(3) Correlation

(3) 2000DEN/DEN

DfH0(R)Z38.4G1.0 (160.7G4.2)

Cyclo-pentane, substituted

X

(1) 94.9G1

397.1G4.2

(1) Iodination

(1) 1970FUR/GOL

(2) 95.0G2

397.5G8.4

(2) AE

(2) 1976LOS/TRA

(3) 96.0G0.2

401.7G0.8

(3) Kinetics

(3) 1978APP/KLU

(4) 95.6G1

400.0G4.2

(4) Radical buffer

(4) 1982CAS/GRI

(5) 97.6

408.5

(5) Correlation

(5) 2001TUM/DEN

Me

(5) 93.7

392.3

Et

(5) 93.7

392.2

Ph

(6) 81.9

342.7

(6) Correlation

(6) 1994TUM/DEN

cyclo-C5H9

(7) 91.3

382.2

(7) Correlation

(7) 2005DEN/TUM

H XaH DfH0(R)Z25.3G1.0 (105.9G4.2)

(continued)

7366—CHAPTER 3—6/2/2007—13:05—JEBA—15359—XML MODEL B – pp. 19–145

34

Comprehensive Handbook of Chemical Bond Energies

Table 3.3 (continued) C–H BDEs in Cyclic Hydrocarbons

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) 3-tert-Butylbi-cyclo(1.1.1)-

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

109.7G3.3

459.0G13.8

GPA

2002REE/KAS

98.8G1

413.4G4.2

Polanyi plot

1971FER/WHI

w102

w426.8

GPA

1988KAS/CHO

(1) 73G5

305.4

(1) Review

(1) 1982MCM/GOL

(2) 73.2 (3) 74.3

306.3 310.9

(2) Kinetics (3) VLPP

(2) 1985DEA (3) 1991STE/BRO

(4) 74.3

310.9

(4) PAC

(4) 1997LAA/MUL

(5) 79.1

330.9

(5) Correlation

(5) 2001TUM/DEN

(1) 70

292.9

(1) Pyrolysis

(1) 1968JAM/SUA

(2) 76.0G1.2 (3) 73G2

318.0G5.0 305.4G8.4

(2) SPST (3) PAC

(2) 1986TSA (3) 1989GRI/WAY

pentane H

tBu

Spiro-pentane

H H 0

DfH (R)Z91.0G1.0 (380.7G4.2)

Spiro-pentane

H

1,3-cyclo-Hexadiene

H H 0

DfH (R)Z47.6(199.2)

1,4-cyclo-Hexadiene, substituted

X H X

H

(4) 77

322.2

(4) PAC

(4) 1999CIR/KOR

(5) 75.0

313.6

(5) Correlation

(5) 2001TUM/DEN

(5) 80.4

336.4

XaH DfH0(R)Z48.2G1.2 (201.7G5.0) Me

7366—CHAPTER 3—6/2/2007—13:05—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

35

Cyclo-hexene, substituted

X' X H XaH,X 00 aH DfH0(R)Z28.6(119.7)

(1) 81.9

342.7

(1) AOP

(1) 1988BOR/CHE

(2) 87G3

364G13

(2) Mol. beam

(2) 1989ZHA/CON

(3) 81.6

341.5

(3) Correlation

(3) 2000DEN/DEN

H

Me

(4) 81.0

338.9

(4) Correlation

(4) 2001TUM/DEN

Me

H

(4) 79.5

332.7

78.0

326.2

Correlation

2001TUM/DEN

Cyclo-hexene, substituted

H H Me

Me

Cyclo-hexane, substituted

(1) 96.2

402.5

(1) Kinetics

(1) 1978APP/KLU

X

(2) 99.5

416.3

(2) SPST

(2) 1981TSA

(3) 96.4G0.6

403.3G2.5

(3) EPR

(3) 1982CAS/GRI

(4) 98 (5) 97.7

410.0 408.8

(4) PAC (5) Correlation

(4) 1999CIR/KOR (5) 2005DEN/TUM

Me

(5) 94.3

394.5

Et

(5) 94.5

395.5

CHaCH2

(5) 81.7

341.8

H XaH DfH0(R)Z18G1.5 (75.3G6.3)

Ph

(6) 85.2

356.4

(6) Correlation

(6) 2000DEN/DEN

CCl3

(7) 93.5

391.1

(7) Correlation

(7) 2005DEN/TUM

cyclo-C6H11

(7) 92.3

386.3

(Z)-1,2-Me2

93.9

392.8

Correlation

2001TUM/DEN

(E)-1,2-Me2

97.4

407.7

(Z)-1,3-Me2

93.9

393.0

(E)-1,3-Me2

93.3

390.3

(Z)-1,4-Me2

93.7

392.0

Cyclo-hexane, substituted

Z E

(continued)

7366—CHAPTER 3—6/2/2007—13:05—JEBA—15359—XML MODEL B – pp. 19–145

36

Comprehensive Handbook of Chemical Bond Energies

Table 3.3 (continued) C–H BDEs in Cyclic Hydrocarbons

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol 94.8

(E)-1,4-Me2

1,3,5-cyclo-Heptatriene

H H

parentheses)

References

396.6

(1) 82.9G7

346.9G29.3

(1) EI

(1) 1960HAR/HON

(2) 73G1

305.4G4.2

(2) Pyrolysis

(2) 1969VIN/DAU

(3) 73G2

305.4G8.4

(3) ICR

(3) 1979BAR/SCO

(4) 76.6G3

320.5G12.6

(4) ICR

(4) 1980DEF/MCI

306.3G8.4

(5) Review

(5) 1982MCM/GOL

83.0

347.3

Correlation

2001TUM/DEN

82.8

346.6

Correlation

2001TUM/DEN

(1) 93G3 (2) 94.0

389.1G12.6 393.3

(1) Polanyi plot (2) Kinetics

(1) 1966KER (2) 1970JON/WHI

DfH0(R)Z68.2G3 (285.3G12.6) (5) 73.2G2

1,3-cyclo-Heptadiene

kJ/mol

Methods (reference in

H H

Cyclo-heptene

H H

Cyclo-heptane, substituted

X H

(3) 92.5G1

387.0G4.2

(3) Photobromin.

(3) 1971FER/WHI

(4) 92.5G1

387.0G4.2

(4) Review

(4) 1982MCM/GOL

(5) 96.5

403.9

(5) Correlation

(5) 2001TUM/DEN

Me

(5) 93.2

390.0

Et

(5) 93.8

392.4

(1) 96.7G2.5 (2) 99.4

404.6G10.5 415.9

Iodination

(1) 1970ONE/BAG (2) 1971DAN/TIP

XaH DfH0(R)Z12.1G1 (50.6G4.2)

Norbornane

7 3 2

4 1 5 6

H DfH0(R)Z32.6G2.5 (136.4G10.5)

7366—CHAPTER 3—6/2/2007—13:05—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

37

Quadricyclane

3 H

4 5

6

2

7

1

DfH0(R)Z138.3G1.3

109.4G1.3

457.7G5.4

Ion flow tube

1996LEE/DEP

111.5G1.3

466.5G5.4

Ion flow tube

1996LEE/DEP

115.6G1.9

483.7G7.9

Ion flow tube

1996LEE/DEP

102G4

426.8G16.7

GPA

1997HAR/EMR

97.7

408.8

Kinetics

1971DAN/TIP

(578.6G5.4)

Quadricyclane

3 5 1

H 6

4 2

7

DfH0(R)Z140.4G1.3 (587.4G5.4)

Norboradine

H

H 7

3 2

4 1

5 6

DfH0(R)Z122.3G1.9 (511.7G7.9)

Cubane

H

DfH0(R)Z198.6G4 (830.9G16.7)

Bicyclo-octane

H DfH0(R)Z22.0 (92.0)

(continued)

7366—CHAPTER 3—6/2/2007—13:06—JEBA—15359—XML MODEL B – pp. 19–145

38

Comprehensive Handbook of Chemical Bond Energies

Table 3.3 (continued) C–H BDEs in Cyclic Hydrocarbons

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Cyclo-octadiene

H H

79.3

331.8

Correlation

2001TUM/DEN

83.0

347.1

Correlation

2005DEN/TUM

85.4

357.2

Correlation

2001TUM/DEN

95.7 94.4

400.2 395.0

Correlation

2001TUM/DEN

93.7

392.3

70.7

295.6

Correlation

2001TUM/DEN

96.3

402.9

Correlation

2001TUM/DEN

94.4

394.8

Cyclo-octadiene H H

Cyclo-octene

H H

Cyclo-octane, substituted

X H XaH Me Et

Spiro(2.5)-octa-4,6-diene

H

H

Cyclo-nonanes, substituted

X H XaH Me

7366—CHAPTER 3—6/2/2007—13:06—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

39

Adamantane H

12

(1) 97.0

405.8

(1) Kinetics

(1) 1971DAN/TIP

(2) 96.2

402.5

(2) AP

(2) 1998AUB/HOL

DfH0(R, at 1 site)Z12.3 (51.5)

(3) 98.5 (4) 93.0

412.0 389.0

(3) Correlation (4) Derived

(3) 2001TUM/DEN (4) 2002MIR/LEB

DfH0(R, at 2 site)Z14.8 (61.9)

(2) 100.2 (3) 98.5

419.2 412.0

(5) 98.4

411.7

(5) PES

(5) 1986KRU/BEA

96.7

404.5

Correlation

2001TUM/DEN

96.7

404.7

Correlation

2001TUM/DEN

98.0

410.0

Correlation

2001TUM/DEN

93.5

391.1

Correlation

2001TUM/DEN

95.6

400.0

Correlation

2001TUM/DEN

90.2

377.4

Correlation

2001TUM/DEN

Cyclo-decane cyclo-C10H19–H

Cyclo-undecane cyclo-C11H21–H

Cyclo-dodecane cyclo-C12H23–H

(Z)-Decalin

H

H

(E)-Decalin

H H

(Z)-Pinane

Me

Me H

Me

7366—CHAPTER 3—6/2/2007—13:06—JEBA—15359—XML MODEL B – pp. 19–145

40

Comprehensive Handbook of Chemical Bond Energies

3.4

Aromatic hydrocarbons

Table 3.4 C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) Benzene

H DfH0(R)Z78.9G0.8 (330.1G3.3) C6D5–D

reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 112.3G1

469.9G4.2

(1) Iodination

(1) 1967ROD/GOL

(2) 111.2G0.8

465.3G3.3

(2) GPA

(2) 1994BER/ELL

(3) 113.5G0.5

474.9G2.1

(3) Ion flow tube

(3) 1995DAV/BIE

(4) 113.2G2

474G8

(4) Recommend.

(4) 1996TSA

(5) 112.9G0.5

472.2G2.2

(5) GPA, revised

(5) 2002ERV/DET

(6) 113.5G0.5

474.9G2.1

(6) GPA

(6) 2003REE/HAR

Phenyl

H

1

6 5

4

H 2 3 H

H H C–H at site 2

(1) 79.9G3.1

334.3G13.0

(1) CID

(1) 1994WEN/SQU

(2) 76.7G3.1

321G13

(2) FT-MS

(2) 2004PRA/FAT

3

(1) 95.3G3.2

398.7G13.4

4

(1) 110.6G3.4

462.8G14.2

109.2G5.6

456.9G23.4

CID

2002LAR/NAS

112G4

468.6G16.7

GPA

2004SLI/MUN

YZ2-C(O)OK

(1) 113.9

476.6

Correlation

(1) 1998WEN/SQU

K

(1) 110.4

461.9

3,5-Didehydrophenyl

H

5-Dehydro-1,3-quinodimethane

CH2

H

CH2

Benzene, substituted

H

Y 3-C(O)O

7366—CHAPTER 3—6/2/2007—13:07—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

41

4-C(O)OK

(1) 112.3

469.9

2-C(O)OH

(1) 114.5

479.1

(1) 114.0

477.0

(1) 113.8

476.1

4-Br

(2) 115.5

483.1

4-Me

(2) 113.5

474.8

4-NO2

(2) 117.3

490.7

%115.3

%482

IR CL

1988WAT/SET

(1) 1980DEF/MCI

DfH0(R)ZK7.9 (K33.1) 3-C(O)OH H0(R)ZK8.4 (K35.1) 4-C(O)OH DfH0(R)ZK8.6 (K36.0)

Toluene, hydridopenta-

(2) 2005DEN/TUM

CH3C6D4–D

Toluene

CH2

H

DfH0(R)Z49.7G0.4 (208.0G1.7)

(1) 88.1G2.2

368.6G9.2

(1) ICR

(2) 88.6

370.7

(2) SPST

(2) 1990WAl/TSA

(3) 88.5G1.5

370.3G6.3

(3) Recommended

(3) 1994BER/ELL

(4) 89.6G1.0

375G4

(4) Recommended

(4) 1996TSA

(5) 90.9G1.2, in sol

380.5G5.1

(5) TR- PAC

(5) 2004MUR/SAN

(5) 89.7G1.2, in gas

375.5G5.0

(1) PA

(1) 1982MEO

Toluene, substituted

Y YZ3-F

4-F

CH2

H (1) 89.4

374.0

(2) 88.8G2.1

371.5G8.8

(10) 89.1

373.0

(2) PES

(2) 1999KIM/WEN

(3) PES

(3) 1986HAY/KRU

(4) Correlation

(4) 2000DEN/DEN

(5) Correlation

(5) 2002KRO/TUM

(2) 87.6G2.1

366.5G8.8

(10) 88.7

371.0

2-Cl

(2) 89.0G3.1

372.4G13.0

3-Cl

(2) 89.8G2.1

375.7G8.8

(4) 89.9

376.1

(6) AOP

(6) 1995BOR/ZHA(c)

4-Cl

(2) 87.5G2.1

366.1G8.8

(7) AOP

(7) 1993ZHA/BOR

(4) 88.7

371.3

(10) 89.7

375.3

(8) CID

(8) 2000HAM/WEN

2-Br

(2) 90.2G3.1

377.4G13.0

(9) CID

(9) 2001HAM/WEN

3-Br

(2) 90.1G3.1

377.0G13.0

(10) Correlation

(10) 2005DEN/TUM

(4) 89.7

375.4

(2) 88.5G3.1

370.3G13.0

(5) 90.8

380.1

4-Br

(continued)

7366—CHAPTER 3—6/2/2007—13:08—JEBA—15359—XML MODEL B – pp. 19–145

42

Comprehensive Handbook of Chemical Bond Energies

Table 3.4 (continued) C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) 2-CH3 3-CH3

kcal/mol

kJ/mol

(3) 87.3

365.3

(10) 89.5

374.6

(3) 87.8

367.4

(10) 89.5

374.3

(3) 87.7

366.9

(10) 89.0

372.5

4-Et

(5) 87.0

363.9

2-iso-Pr

(5) 87.6

366.6

3-iso-Pr

(5) 86.8

363.2

4-Pr

(5) 87.0

363.9

4-CH3

4-tert-Bu

(10) 89.3

373.8

3-CN

(5) 88.7

371.2

4-CN

(5) 88.0

368.0

3-NO2

(5) 89.6

375.0

(6) 86.5

361.9

(10) 88.8

371.4

4-PhO

(10) 90.2

377.3

4-NO2

4-PhSO2

(7) 88

368.2

4-CH2OCH3

(5) 85.4

357.5

3-MeO

(5) 90.5

378.8

4-MeO

(5) 86.6

362.5

3-EtOC(O)

(5) 89.1

372.7

Methods (reference in parentheses)

References

4-EtOC(O)

(5) 89.4

374.1

4-CH(MeO)2

(10) 84.2

352.2

2,4-Cl2

(5) 88.6

370.9

(4) Correlation

(4) 2000DEN/DEN

3,4-Cl2

(5) 88.3

369.6

(5) Correlation

(5) 2002KRO/TUM

2,3-Me2

(5) 89.5

374.3

2,4-Me2

(4) 89.1

373.0

3,5-Me2

(10) 89.4

373.9

(10) Correlation

(10) 2005DEN/TUM

88.6

370.9

Correlation

2000DEN/DEN

Toluene, di-substituted

Toluene, multi-substituted 2,3,4,5,6-Me5

7366—CHAPTER 3—6/2/2007—13:08—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

43

Toluene, other-substituted 3-CH%2

(1) 90.7G2.9

379.5G12.1

3,5-(CH%2)

(2) 88.2G5.0

369.0G20.9

64G3

267.8G12.6

Derived

1990BAR/GRI

87.7

367

AOP

1997CHE/LIU

(1) 84.6

354.0

(1) VLPP

(1) 1981ROB/STE

(2) 86.2

360.7

(2) Proton affinity

(2) 1982MEO

CID

(1) 2000HAM/WEN (2) 2001HAM/WEN

p-iso-Toluene

H H

Toluene bromide C6H5CH2HCBrK

Ethylbenzene, substituted

H CH

Y

CH3

YaH

(3) 85.4G1.5

357.3G6.3

(3) Review

(3) 1982MCM/DOL

(4) 90.3

377.8

(4) Re-anal.

(4) 1998BRO/BEC

(5) 87.0

364.1

(5) Correlation

(5) 2000DEN/DEN

(6) Correlation

(6) 2002KRO/TUM

DfH0(R)Z40.4 (169.0) p-C2H5

(6) 86.5

362.0

p-Br

(6) 87.1

364.6

p-tert-Bu

(6) 86.5

362.1

p-MeOC(O)

(6) 87.0

364.1

2,3,4,5,6-Penta-Et

(7) 90.8

380.2

(7) Correlation

(7) 2005DEN/TUM

98.4G3.1

411.7G12.9

Derived

2005FAT/KAS

84.4

353.1

Correlation

1994TUM/DEN

n-Propylbenzene

(1) 86.1

360.2

(1) PA

(1) 1982MEO

PhCH2C2H5

(2) 87.5

366.2

(2) Correlation

(2) 2000DEN/DEN

Vinylbenzene PhCHaCH2

Prop-2-enylbenzene PhCH2CHaCH2

(continued)

7366—CHAPTER 3—6/2/2007—13:08—JEBA—15359—XML MODEL B – pp. 19–145

44

Comprehensive Handbook of Chemical Bond Energies

Table 3.4 (continued) C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

iso-Propylbenzene, substituted

H

C(CH3)2

Y

YZ2,5-Me2

86.7

362.9

4-tert-Bu

83.5

349.3

Correlation

2005DEN/TUM

2,5-Me2-4-iso-Pr

87.9

367.8

2,4,5-(iso-Pr)3

89.7

375.3

tert-Butylbenzene

98.6

412.6

Correlation

2005DEN/TUM

78.9G2.6

330.1G10.9

FT-MS

2002GLA/MAK

81.5

341.0

AOP

1991BAU/FAS(b)

76.2

318.8

AOP

1991BAU/FAS(b)

82G3

343.1G12.6

Electrochemical

1997KER/ZHA

92.1G3.8

385.3G15.9

Derived

2005FAT/KAS

C6H5C(CH3)2CH2–H

(E)-1-Phenylpropene (E)-Ph-CHaCH-CH2–H

Phenylacetonitrile PhCH2CN

1-Methoxyphenylacetonitrile PhCH(CN)MeO

Cationic niobium h2-acyl

Cl (C5Me5)2 Nb O+

C6H5

C

H C2H5

1-Phenyl-cyclo-propene

H Ph

7366—CHAPTER 3—6/2/2007—13:08—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

45

1-Phenyl-cyclo-butene

1

Ph

4 23

H

85.6G2.6

358.2G10.9

FT-MS

2002GLA/MAK

88.0

268.2

Correlation

2002KRO/TUM

85.2

356.4

Correlation

2002KRO/TUM

H

Cyclo-pentylbenzene

H

Cyclo-hexylbenzene

H

Diphenylmethane

(1) 84G2

351.5G8.4

(1) VLPP

(1) 1991STE/BRO

Ph2CH2

(2) 84.5G0.5

353.5G2.1

(2) Electrochem.

(2) 1991PAR/HAN

DfH0(R)Z72.2G1.0

(3) 85.8

359.0

(3) Re-anal.

(3) 1998BRO/BEC

(4) 85.3

356.8

(4) Correlation

(4) 2000DEN/DEN

(5) 81.8

342.3

(5) AOP

(5) 2002ALN/ZHA

80

334.7

AOP

1989BOR/HAR

89.3G1.0

373.5G4.2

TR-PAC

2004COR/SAN

89.8G1.1

375.8G4.7

TR-PAC

2004COR/SAN

87.0

364.1

Correlation

2000DEN/DEN

2-Phenylpropane

(1) 83.6

349.8

(1) VLPP

(1) 1981ROB/STE

PhCH(CH3)2

(2) 84.4G1.5

353.1G6.3

(2) Review

(2) 1982MCM/GOL

DfH0(R)Z32.0G1.0

(3) 83.2G1

348.1G4.2

(3) PAC

(3) 1997LAA/BOR

(302.1G4.2)

Diphenylmethane, substituted (p-PhC6H4)2CH2

4-Hydroxydiphenylmethane (4-OH-C6H4)CH2C6H5

Bis(4-hydroxyphenyl)methane (4-OH-C6H4)2CH2

1,2-Diphenylethane PhCH2CH2Ph

(133.9G4.2)

(4) 87.3

365.3

(4) Re-anal

(4) 1998BRO/BEC

(5) 84.0

351.6

(5) Correlation

(5) 2005DEN/TUM

(continued)

7366—CHAPTER 3—6/2/2007—13:09—JEBA—15359—XML MODEL B – pp. 19–145

46

Comprehensive Handbook of Chemical Bond Energies

Table 3.4 (continued) C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1,1-Diphenylethane

(1) 81G2

338.9G8.4

(1) VLPP

(1) 1981STE

Ph2C(CH3)CH

(2) 82.8

346.4

(2) Re-anal.

(2) 1998BRO/BEC

(3) 83.4

348.8

(3) Correlation

(3) 2005DEN/TUM

Thiphenylmethane, substituted

Y

C

Y′

H

Y ′′ YZp-H, Y 0 Zp-H, Y 00 Zp-H DfH0(Ph3C)Z93.7G2

(1) 81G2

338.9G8.4

(1) AOP

(1) 1991PAR/HAN

(2) 80.8G3

338.1G12.6

(2) AOP

(2) 1993BOR/ZHA(b)

(3) 79.0

330.5

(3) AOP

(3) 1997ARN/FLO

(4) 82.7

346.0

(4) Correlation

(4) 2000DEN/DEN

(5) 85.4

357.3

(5) Correlation

(5) 2002KRO/TUM

(392.0G8.4) p-MeO, p-MeO, p-MeO

(3) 78.1

326.8

p-MeO, p-MeO, p-H

(3) 79.3

331.8

p-Me, p-Me, p-Me

(3) 79.0

330.5

p-MeO, p-H, p-H

(3) 80.7

337.6

p-Me, p-Me, p-H

(3) 80.3

336.0

p-Me, p-H, p-H

(3) 79.1

331.0

p-tBu, p-tBu, p-tBu

(3) 74.4

311.3

82.3

344.3

AOP

1993BOR/ZHA(b)

77

322.2

AOP

1989BOR/HAR

75.1

314.2

AOP

1991BOR/CHE

Thiphenylmethane, substituted (p-HC6F4)3C–H

1,1,3,3-Tetraphenylpropene Ph2CaCHCH(Ph)2

1,1,3,5,5-Pentaphenyl-1,4pentadiene Ph2CaCHCH(Ph)CHaCPh2

7366—CHAPTER 3—6/2/2007—13:09—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

47

Benzo-cyclo-propene

H

91.1G7.5

381.2G31.4

GPA

1997MOO/LUB

92G4

384.9G16.7

GPA

2000GLA/MAK

114G4

477.0G16.7

GPA

2000BRO/KAS(b)

85.3

357.0

Correlation

2000DEN/DEN

H

Benzo-cyclo-butene

H H

Benzo-cyclo-butadiene

H

Indane

H

H

DfH0(R)Z48.8G2 (204.2G8.4)

Indene

H H

0

DfH (indenyl)Z71 (297.1)

(1) 84G3

351.5G12.6

(1) Review

(1) 1982MCM/GOL

(2) 81.5G0.5

341.0G2.1

(2) Electrochem.

(2) 1991PAR/HAN

(3) 81.1G2.4

339.3G10.0

(3) ICR

(3) 1997ROM/JAN

(4) 83.0

347.3

(4) Re-anal.

(4) 1998BRO/BEC

(5) 81.2

339.9

(5) Correlation

(5) 2001TUM/DEN

(1) AOP

(1) 1992BOR/SAT

(2) VLPP

(2) 1981STE

Indene, substituted

H

H 7 6 5 4

1

2 3

YZ2-Br

Y (1) 80.9

338.5

3-Me

(1) 77.6

324.7

3-tert-Bu

(1) 78.5

328.4

2-Ph

(1) 79.3

331.8

(2) 84G3

351.5G12.6

(continued)

7366—CHAPTER 3—6/2/2007—13:09—JEBA—15359—XML MODEL B – pp. 19–145

48

Comprehensive Handbook of Chemical Bond Energies

Table 3.4 (continued) C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

3-Ph

(1) 75.3

315.1

3-MeO

(1) 76.4

319.7

3-MeS

(1) 74.1

310.0

2-PhS

(1) 80.2

335.6

3-CN

(1) 77.9

325.9

3-cyclo-C4H8N

(1) 70.3

294.1

2-cyclo-C4H8N

(1) 83.5

349.4

3-cyclo-C5H10N

(1) 72.3

302.5

2-cyclo-C5H10N

(1) 82.5

345.2

3-cyclo-OC4H8N

(1) 73.4

307.1

2-cyclo-OC4H8N

(1) 82.8

346.4

2-(4-MeOC6H4)

(1) 79.3

331.8

2-(4-MeC6H4)

(1) 79.1

331.0

3-C(O)NH2

(1) 77.7

325.1

2-C(O)OMe

(1) 79.2

331.4

Methods (reference in parentheses)

References

3-C(O)OMe

(1) 77.6

324.7

6-NO2-3-Me

(1) 78.4

328.0

1,2,3-Ph3

(1) 75.8

317.1

(1) 82.9G1.2 (2) 83.6

346.9G5.0 349.6

(1) PAC (2) Correlation

(1) 1997LAA/MUL (2) 2000DEN/DEN

(3) Correlation

(3) 2002KRO/TUM

(4) Correlation

(4) 1994TUM/DEN

Correlation

2002KRO/TUM

Tetralin

X

H X' H

XaH

X 0 aH

DfH0(R)Z37G1.2 (154.8G5.0) Me Me

H Me

(3) 82.6

345.6

(3) 80.4

336.4

(4) 79.3

331.8

(4) 80.5

336.8

80.9

338.4

1,5,7-Trimethyltetralin

H CH3

CH3

CH3

7366—CHAPTER 3—6/2/2007—13:10—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

49

1,4-Dihydronaphthalene

H

H 83.0

347.3

Re-anal. of

1997RUC/GER

pyrolysis data

1,2-Dihydronaphthalene

H H

Naphthalene

H 1

(1) 86.0

359.8

(1) Re-anal.

(1) 1997RUC/GER

(2) 80.4

336.5

(2) Correlation

(2) 2002KRO/TUM

(1) 112.2G1.3

469.4G5.4

(1) FT MS

(1) 2000REE/KAS

(2) 113.4G5.2

474.5G21.8

(2) Neg. ion cycle

(2) 2001LAR/SQU

(3) 112.8G3.3

472G14

(3) Neg. ion

(3) 2001ERV/RAM

spectroscopy

2

DfH0(R)Z96.0G1.3 (401.7G5.4)

Naphthalene

1

H 2

(1) 111.9G1.4

468.2G5.9

(1) FT MS

(1) 2000REE/KAS

(2) 115.4G4.9

482.8G20.5

(2) Neg. ion cycle

(2) 2001LAR/SQU

(3) 113.8G4.8

476G20

(3) Negative ion

(3) 2001ERV/RAM

spectroscopy DfH0(R)Z95.7G1.4 (400.4G5.9)

2-Naphthyl anion

H 7 6 H

H

H

8

1

5

4

H

H

C–H at 3 site 6 site

2 3 H

93G3

389.1G12.6

106G4

443.5G16.7

Derived

2000REE/HAR

(continued)

7366—CHAPTER 3—6/2/2007—13:10—JEBA—15359—XML MODEL B – pp. 19–145

50

Comprehensive Handbook of Chemical Bond Energies

Table 3.4 (continued) C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

2-Naphthyl radical

H

H

8

1

5

4

H

H

H 7 6

H

2 3

H

C–H at 3 site 6 site

77G4

322.2G16.7

107G4

447.7G16.7

69G3

288.7G12.6

Derived

2000REE/HAR

Derived

1990BAR/GRI

1-Methylene-1,4dihydronaphthalene

H H

1-Methyl-naphthalene H CH 1

X'

X

2

X 0 aH

XaH

(1) 84.3G1.5

352.7G6.3

(1) VLPP

(1) 1980MCM/TRE

(2) 85.1G1.5

356.1G6.3

(2) Review

(2) 1982MCM/GOL

DfH0(1-R)Z60.4 (252.7)

(3) 87.3

365.1

(3) Correlation

(3) 2000DEN/DEN

CN

X 0 aH

(4) 81.3

340.2

(4) AOP

(4) 1988BOR/CHE(b)

H

X 0 ZMe

(5) 86.8

363.1

(5) Correlation

(5) 2002KRO/TUM

YaH

(1) 85.6

358.3

(1) Correlation

(1) 2002KRO/TUM

H

(1) 87.1

364.6

2-Methyl-naphthalene H

Y

XaH Me

78 6 5

1

2 4 3

CH

X

7366—CHAPTER 3—6/2/2007—13:10—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

51

SO2Ph

H

(2) 89

372.4

(2) AOP

(2) 1988BOR/BAU

CN

H

H

3-Me

(3) 81.4

340.6

(3) AOP

(3) 1988BOR/CHE(b)

(1) 86.8

363.3

H

6-Me

(1) 86.8

363.2

87.1

364.4

Correlation

2000DEN/DEN

81

338.9

AOP

1989BOR/HAR

1-Ethylnaphthalene H

CH3

C 1

H 2

4,5-Methylene-phenathrene 5

4

H2C CH

H

9,10-Dihydroanthracene, substituted H

X

H

X'

00

XaH

X aH,

DfH0(9,10-dihydroanthracen-9-

(1) 78

326.4

(1) AOP

(1) 1988BOR/CHE

(2) 78

326.4

(2) PAC

(2) 1989GRI/SIM

(3) 77

322.2

(3) Kinetics

(3) 1990MAL/MCM

(4) 76.3

319.2

(4) VLPP

(4) 1991STE/BRO

(5) 83.0

347.3

(5) Re-anal.

(5) 1997RUC/GER

(6) AOP

(6) 1991BOR/CHE

yl)Z62.4 (261.1) H

Ph

Me

Me

(5) 84.5

353.5

(6) 79

330.5

(5) 81.5

341.0

(7) 77

322.2

(7) PAC

(7) 1989GRI/SIM

(8) 78.1

326.7

(8) Correlation

(8) 2005DEN/TUM

84.9

355.2

Re-anal. of

1997RUC/GER

9,10-Dihydroanthracene, substituted H

H

pyrolysis data Ph

Ph

(continued)

7366—CHAPTER 3—6/2/2007—13:10—JEBA—15359—XML MODEL B – pp. 19–145

52

Comprehensive Handbook of Chemical Bond Energies

Table 3.4 (continued) C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

9,10-Dihydroanthracene, substituted Me

H

H

Me

Me

Me

83.3

348.5

Re-anal. of

1997RUC/GER

pyrolysis data

9-Methylene-6,10,dihydroanthracene H

H

77G3

322.2G12.6

Derived

1990BAR/GRI

(1) 1991STE/BRO

Xanthene, substituted X

H

O

XaH

(1) 74

309.6

(1) VLPP

(2) 75.5

315.9

(2) AOP

(2) 1991BOR/CHE

(3) 75.2

314.6

(3) AOP

(3) 1997ARN/FLO

(4) Re-anal.

(4) 1997RUC/GER

(4) 80.7

337.6

Me

(4) 77.6

324.7

CN

(5) 69

288.7

(5) AOP

(5) 1992ZHA/BOR

SO2Ph

(6) 82

343.1

(6) AOP

(6) 1988BOR/CHE

(7) AOP

(7) 1993ARN/FLO

Ph

p-MeC6H4 p-MeOC6H4 p-FC6H4 p-ClC6H4 p-CF3C6H4

(5) 76

318.0

(3) 74.6

312.1

(7) 76.7

320.9

(5) 75.6

316.3

(5) 74.3

310.9

(7) 76.2

318.8

(5) 76.8

321.3

(7) 76.4

319.7

(5) 73.9

309.2

(7) 78.1

326.8

(5) 78.3

327.6

(7) 78.1

326.8

7366—CHAPTER 3—6/2/2007—13:11—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

53

9,10-Dihydroacridine, substituted H

H

X

XZNH

80.0

NCH3

334.7

Re-anal. of

1997RUC/GER

pyrolysis data

80.0

334.7

74.6

312.1

AOP

1997ARN/FLO

80.2

335.6

Re-anal. of

1997RUC/GER

Thioxanthene H

H

S

10-Hydroanthracen-9-one H

H

pyrolysis data

O

Fluorenes, substituted H

H

(1) 80.1

335.1

(1) VLPP

(2) 82.2

343.9

(2) Electrochem.

(2) 1992PAR

(3) 81.2G2.4

339.7G10.0

(3) ICR

(3) 1997ROM/JAN

YaH

(4) 82.0G2

343.1G8.4

(4) Re-anal.

(4) 1994RAK/VER

DfH0(9-fluorenyl)Z71.7G2

(5) 82.6

345.6

(5) Re-anal.

(5) 1997RUC/GER

(6) AOP

(6) 1992ZHA/BOR

(7) AOP

(7) 1994ZHA/BOR(b)

(8) AOP

(8) 1993ZHA/BOR

9

8

7 6

5

1

2 4 3

Y

(1) 1991STE/BRO

(300.0G8.4) 2-PhSO2

(6) 80

334.7

2-CN

(6) 80

334.7

2-NO2

(6) 81

338.9

2-MeO

(7) 80

334.7

2-Me2N

(6) 80

334.7

2-PhSO2

(8) 79.7

333.5

2,7-Br2-9-CO2Me

(6) 76.5

320.1

(continued)

7366—CHAPTER 3—6/2/2007—13:11—JEBA—15359—XML MODEL B – pp. 19–145

54

Comprehensive Handbook of Chemical Bond Energies

Table 3.4 (continued) C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Fluorenes, substituted X

H 9

XZ9-CN 9-SO2Ph

(1) 74.8

313.0

(1) 81.9

342.7

9-PhS

(1) 74.6

312.1

9-Me2N

(1) 71.5

299.2

AOP

(1) 1991BOR/ZHA

9-(2,4,6-Me3C6H2)

(2) 74.5

311.7

(2) 1991BOR/ZHA

9-PhCH2(Me)N

(3) 72.5

303.3

(3) 1992ZHA/BOR

9-(iso-Pr)2N

(3) 73

305.4

(3) 76

318.0

(3) 68

284.5

(3) 72

301.2

(3) 72

301.2

(3) 71

297.1

9-Ph

(6) 74

309.6

9-C6F5

(4) 78.2

327.2

(4) 1993ZHA/BOR

9-mesityl

(6) 74.5

311.7

(5) 1994ZHA/BOR(b) (6) 1994ZHA/BOR(c)

Me

9 Me Me

9

N

9

N

9

N

9

N

9-MeOCO

(6) 76

318.0

9-cyclo-C4H8N

(6) 68

284.5

7366—CHAPTER 3—6/2/2007—13:11—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

55

9-cyclo-C5H10N

(6) 72

301.2

9-PhCH(Me)N

(6) 72.5

303.3

(6) 72

301.2

(6) 71

297.1

(7) 75.4

315.5

(7) 1994BOR/ZHA

333.5

(9) 1998BRO/BEC

(10) 78.5

328.5

(10) 2002KRO/TUM

9-Et

(7) 76.2

318.8

9-n-Pr

(7) 76.1

318.4

9-iso-Pr

(7) 77.3

323.4

9-sec-Bu

(7) 75.1

314.2

9-tert-Bu

(7) 79.9

334.3

9-CH(Me)(CH2)2C(Me)N

9-C(Me)2(CH2)2C(Me)2N 9-Me

DfH0(R)Z64.1G2 (268.2G8.4) (9) 79.7G2

9-neo-C5H11

(7) 73.6

307.9

9-CPh3

(8) 77.2

323.0

9-PhC(Me)2CH2

(7) 73.8

308.8

9-PhCH2

(7) 75.9

317.6

9-MeS

(7) 74.6

312.1

9-EtS

(7) 74.3

310.9

9-iPrS

(7) 74.3

310.9

9-tert-BuS

(7) 74.8

313.0

9-PhS

(7) 74.8

313.0

9-MeSO2

(7) 82.1

343.5

9-EtSO2

(7) 81.4

340.6

9-iso-PrSO2

(7) 81.1

339.3

9-PhSO2

(7) 79.7

333.5

9-(p-BrPh)SO2

(7) 82.0

343.1

9-MeO

(7) 73.0

305.4

9-EtO

(7) 72.9

305.0

9-iso-PrO

(7) 72.7

304.2

9-tert-BuO

(7) 74.0

309.6

9-PhO

(7) 74.3

310.9

9-Me3SiCH2

(11) 76.3

319.2

9-SiMe3

(8) 82.5

345.2

9-SiEt3

(8) 81.2

339.7

9-SiPh3

(8) 80.6

337.2

9-Me3NC, ClK

(5) 84.6

354.0

9-PyNC, BrK

(4) 80.9

338.5

(5) 81.6

341.4

(12) 83.0

347.3

C

9-Ph3P , Br

K

9-nBu3PC, BrK

(8) 1995ZHA/ZHA

(11) 1996ZHA/BOR

(12) 2000CHE/LIU

(continued)

7366—CHAPTER 3—6/2/2007—13:12—JEBA—15359—XML MODEL B – pp. 19–145

56

Comprehensive Handbook of Chemical Bond Energies

Table 3.4 (continued) C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) 9-Ph3AsC, BrK C

9-Me2S , Br

K

9-Me2SeC, BrK C

9-tBu2Te , Br

K

9-Me3NC(2-PhSO2), BrK

kcal/mol

kJ/mol

(12) 82.6

345.6

(12) 77.6

324.7

(12) 78.7

329.3

(12) 77.3

323.4

(4) 85.7

358.6

80

334.7

Methods (reference in parentheses)

References

Fluorenes, substituted H H

Y

YZp-Cr(CO)3 C

AOP

1994ZHA/BOR(b)

p- Mn(CO)3

81

338.9

p-C-Fe(C5H5)

80

334.7

79.3

332.0

Correlation

2002KRO/TUM

84.0

351.3

Correlation

2005DEN/TUM

78.8

329.7

Correlation

1994STUM/DEN

1,2,3,4,4a,9a-Hexahydrofluorene H

H

Acenaphthene H

H

3,4,5-Trihydroacenaphthene H

H

7366—CHAPTER 3—6/2/2007—13:12—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

57

Tetrahydroacenaphthene H H

75.8

317.0

Correlation

2002KRO/TUM

84.3

352.7

Correlation

2005DEN/TUM

84.3

352.7

Correlation

2005DEN/TUM

117G4

489.5G16.7

GPA

2002KAS/BRO

84G2

351.5G8

Derived

2001BRO/KAS

Methylacenaphthene CH2

H

4-Methylacenaphthene

H CH2

Acenaphthylene H

H

Acenaphthylene radical H

9-Anthracenylmethanes, substituted H

CH

X

(1) 81.0

338.9

(1) Analysis of exp.

(1) 1980MCM/TRE

(2) 81.8

342.3

(2) Review

(2) 1982MCM/GOL

(3) 81.5

341.0

(3) AOP

(3) 1991BOR/CHE

(4) 84.1G0.5

351.9G2.1

(4) Electrochem.

(4) 1991PAR/HAN

(5) 81.5

341.0

(5) AOP

(5) 2002ALN/ZHA

Y

YaH, XaH DfH0(9-anthracenylmethyl) Z80.7 (337.6) CN MeO

(6) 78.7

329.3

(6) AOP

(6) 1991BAU/FAS(b)

(7) 78.9

330.1

(7) AOP

(7) 1993ZHA/BOR(b)

(6) 77.4

323.8

(7) 77.5

324.3

(continued)

7366—CHAPTER 3—6/2/2007—13:12—JEBA—15359—XML MODEL B – pp. 19–145

58

Comprehensive Handbook of Chemical Bond Energies

Table 3.4 (continued) C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) PhO

kcal/mol

kJ/mol

(6) 78.6

328.9

(7) 79.9

334.3

PhCO

(7) 84.2

352.3

NO2

(7) 86.1

360.2

PhS

(7) 81.0

338.9

PhSO2

(7) 84.7

354.4

YZCN, XZMeO

(6) 73.7

308.4

PhO

(6) 72.9

305.0

(1) 80.8

338.1

(1) 81.8

342.3

Methods (reference in parentheses)

References

Anthracenes, substituted CH2

H

9

8

1

10

Y

YZCl Me

(2) 78.1

326.7

MeO

(1) 81.4

340.6

Ph

(1) 81.8

342.3

CHO

(1) 80.4

336.4

PhCO

(1) 82.3

344.3

CN

(1) 80

334.7

NO2

(1) 82.6

345.6

PhS

(1) 80.8

338.1

78.7

329.3

78.0

326.4

(1) AOP

(1) 1993ZHA/BOR(b)

(2) Correlation

(2) 2002KRO/TUM

AOP

1991BAU/FAS(b)

Anthracenes, substituted CN X

XaH MeO

C

H

7366—CHAPTER 3—6/2/2007—13:12—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

59

9-Phenanthrenylmethane 1

10

CH2

9

H

8

DfH0(9-phenanthrenylmethyl)

85.1G1.5

356.1G6.5

VLPP

1982MCM/GOL

Z74.4 (311.3)

9,10-Dihydrophenanthrene H H

10 9

(1) 89.6

374.9

(1) Re-anal.

(1) 1997RUC/GER

(2) 82.1

343.7

(2) Correlation

(2) 2000DEN/DEN

(3) 81.6

341.6

(3) Correlation

(3) 2002KRO/TUM

Phenalene H H

(1) 64G3

267.8G12.6

(1) AOP

(1) 1990BAU/GOS

(2) 74.0

309.6

(2) Re-anal.

(2) 1997RUC/GER

Benzanthrene H H

(1) 66G3

276.1G12.6

(1) AOP

(1) 1990BAU/GOS

(2) 76.0

318.0

(2) Re-anal.

(2) 1997RUC/GER

86.0G4.8

359.9G20

PIMS

1997LIN/LIF

78.7

329.3

AOP

1991BOR/CHE

Triphenylene radical cation

H

1,2-Benzofluorence H H

8

9

1

(continued)

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60

Comprehensive Handbook of Chemical Bond Energies

Table 3.4 (continued) C–H BDEs in Aromatic Hydrocarbons BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

2,3-Benzofluorence H H 8

9

(1) 78.8 1

329.7

(1) VLPP

(1) 1991STE/BRO

(2) 78.4

328.0

(2) AOP

(2) 1991BOR/CHE

(3) 78

326.3

(3) AOP

(3) 2002ALN/ZHA

88.6

370.8

Correlation

2002KRO/TUM

85.7

358.7

Correlation

2002KRO/TUM

81.6

341.4

Correlation

2000DEN/DEN

81.6

341.4

Correlation

2002KRO/TUM

Methylbenzo(b)phenanthrene H

CH2

6-Methylchrysene CH2

H

1,2-Dihydropyrene H H 1 2

H H

1,2,3,6-Tetrahydropyrene H H

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BDEs of C–H Bonds

61

(E)-9,10-Diphenyl-9,10dihydroanthracene

H

81.5

341.0

Re-anal. of

1997RUC/GER

pyrolysis data

H

(Z)-9,10-Diphenyl-9,10dihydroanthracene

H

79.4

H

332.2

Re-anal. of

1997RUC/GER

pyrolysis data

Dodecahedrane

H

3.5

92G3

384.9G12.6

FT-MS

2000BRO/KAS

Halogenated hydrocarbons

Table 3.5 C–H BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Trifluoromethane

(1) 106.7G1

446.4G4.2

(1) Photolysis

(1) 1972BAS/WHI

H–CF3

(2) 106.2

444.2

(2) Spectroscopy

(2) 1995APO/TUL

(3) 107.4

449.4

(3) Derived

(3) 1997ASH/RUS

DfH0(R)ZK111.2G0.4 (K465.3G1.7)

(continued)

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62

Comprehensive Handbook of Chemical Bond Energies

Table 3.5 (continued) C–H BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(4) 106.4G0.7

445.2G2.9

(4) Derived

(4) 1998RUS/MIC

(5) 108.9

455.6

(5) SPST

(5) 1999TSA

Difluoromethane H–CHF2

(1) 97.4G1.3

407.5G5.4

(1) Kinetics

(1) 1969PRI/PER

DfH0(R)ZK57.1G1

(2) 101G2

422.6G8.4

(2) Elimination

(2) 1971KER/TIM

(3) 103.2G1

431.8G4.2

(3) Iodination

(3) 1983PIC/ROD

(4) 101G2

422.6G8.4

(4) Kinetics

(4) 1983MAR/PAR

(5) 101.8G1.1

425.8G4.6

(5) Review

(5) 2001LAZ/PRO

(K238.9G4.2)

Fluoromethane

(1) 101.3G1

423.8G4.2

(1) Iodination

(1) 1983PIC/ROD

H–CH2F

(2) 100G2

418.4G8.4

(2) Kinetics

(2) 1983MAR/PAR

(1) 101.6G1

425.1G4.2

(1) Review

(1) 1982MCM/GOL

(2) 100.7G2

421.3G8.4

(2) Photobromin.

(2) 1992MIY/TSC

Dichlorofluoromethane

(1) 98.9G1.2

413.8G5.0

(1) Bromination

(1) 1987TSC/PAD

H–CCl2F

(2) 98.2G2

410.9G8.4

(2) Photobromin.

(2) 1992MIY/TSC

(3) 97.7

408.8

(3) Review

(3) 1997POU/PAU

99.3G3

415.5G12.6

Derived from

1991GUR/VEY

DfH0(R)ZK7.6G1 (K31.8G4.2)

Chlorodifluoromethane H–CClF2 DfH0(R)ZK66.7G2 (K279.1G8.4)

DfH0(R)ZK21.3G2 (K89.0G8.4)

Difluorobromomethane

DfH0 in ref.

H–CBrF2

Chlorofluoromethane

(1) 100.8G2.4

421.7G10.0

(1) Bromination

(1) 1987TSC/PAD

H–CHClF

(2) 99.4

415.9

(2) Review

(2) 1997POU/PAU

DfH0(R)ZK14.5G2.4 (K60.7G10.0)

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BDEs of C–H Bonds

63

Trichloromethane

(1) 95.8G1

400.8G4.2

(1) Bromination

(1) 1973MEN/GOL

H–CCl3

(2) 95.2 (3) 94.9G2

398.3 397.1G8.4

(2) Review (3) EI

(2) 1983WEI/BEN (3) 1988HOL/LOS

DfH0(R)Z17.0G0.6 (71.1G2.5)

(4) 93.8G0.6

392.5G2.5

(4) PIMS detect.

(4) 1991HUD/JON

(5) 87.7, at 0 K

367.1

(5) Spectroscopy

(5) 1994APO/TUL

Dichloromethane

(1) 98.4G1.2

411.7G5.0

(1) Bromination

(1) 1987TSC/PAD

H–CHCl2

(2) 97.2G2

406.7G8.4

(2) EI

(2) 1988HOL/LOS

DfH0(R)Z20.8G0.4

(3) 96.2G0.6

402.5G2.7

(3) PIMS detect.

(3) 1996SEE

(87.1G1.6)

(4) 97.3G1.0

407.1G4.2

(4) Review

(4) 1997POU/PAU

(5) 95.7G0.5

400.6G2.0

(5) TPEPICO

(5) 2006LAG/BAE(b)

Chloromethane

(1) 100.8G1

421.7G4.2

(1) Bromination

(1) 1987TSC/PAD

H–CH2Cl

(2) 99.4G2

415.9G8.4

(2) EI

(2) 1988HOL/LOS

(3) 100.1G0.6

419.0G2.3

(3) PIMS detect.

(3) 1996SEE

(4) 100G2

418.4G8.4

(4) Review

(4) 1997POU/PAU

(5) 99.9

418

(5) FT-ICR

(5) 2000BOR/ING

98.6G5

413G21

Derived from

1991GUR/VEY

DfH0(R)Z28.0G0.7 (117.2G2.9)

Bromochlorofluoromethane

DfH0 in ref.

H–CFClBr

Bromochloromethane

(1) 93.9

393

(1) FT-ICR

(1) 2000BOR/ING

H–CHClBr DfH0(R)Z34.2G1.4

(2) 97.0G0.6

406.0G2.4

(2) PIMS detect.

(2) 2003SEE

92.5G5

387G21

Derived from

1991GUR/VEY

(143G6)

Bromodichloromethane

DfH0 in ref.

H–CCl2Br

Dibromochloromethane

88.7G5

371G21

Tribromomethane H–CBr3

Derived from

1991GUR/VEY

DfH0 in ref.

H–CClBr2

(1) 96.0G1.6 (2) 95.4G2

401.7G6.7 399.2G8.4

(1) Bromination (2) EI

(1) 1971KIN/GOL (2) 1988HOL/LOS

DfH0(R)Z51.3 (214.8)

(continued)

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64

Comprehensive Handbook of Chemical Bond Energies

Table 3.5 (continued) C–H BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Dibromomethane

(1) 103.7G2

433.9G8.4

(1) TCT

(1) 1958PRI/TRO

H–CHBr2

(2) 99.7G1.8

417.1G7.5

(2) Bromination

(2) 1987TSC/PAD

(3) 97.9G2

409.6G8.4

(3) EI

(3) 1988HOL/LOS

(4) 98.2

411

(4) Review

(4) 2000BOR/ING

Bromomethane

(1) 102.0G2

426.8G8.4

(1) TCT

(1) 1958PRI/TRO

H–CH2Br

(2) 101.6G1

425.1G4.2

(2) Bromination

(2) 1987TSC/PAD

(3) 100.8G2

421.7G8.4

(3) EI

(3) 1988HOL/LOS

(4) 102.1G0.6

427.2G2.4

(4) PIMS detect.

(4) 2003SEE

101.1G7

423G29

Derived from

1991GUR/VEY

DfH0(R)Z45.0G2.2 (188.3G9.2)

DfH0(R)Z40.9G0.6 (171.1G2.7)

Tetraiodomethane

DfH0 in ref.

H–CI3

Diiodomethane

103G2

431.0G8.4

Review

1970ONE/BEN

Iodomethane

(1) 103G2

431.0G8.4

(1) Review

(1) 1970ONE/BEN

H–CH2I

(2) 103.5G2

433.0G8.4

(2) EI

(2) 1988HOL/LOS

DfH0(R)Z54.9G2 (229.7G8.4) D–CH2I

(3) 103.2G0.7 (4) 105.6

431.6G2.8 441.8

(3) Kinetics (4) Review

(3) 2002SEE (4) 1974GUR/KAR

D–CD2I

(5) 106.1G1.4

444G6

(5) Pyrolysis

(5) 2005SKO/MIS

Pentafluoroethane

(1) 103.1G1.5

431.4G6.3

(1) Kinetics

(1) 1972BAS/WHI

CF3CF2–H

(2) 102.7G0.5

429.7G2.1

(2) Photolysis

(2) 1981EVA/WHI

(3) 106G2.3

443.8G9.6

(3) Combined

(3) 2005YAN.HUA(b)

(1) 103.0G4.5 (2) 107.1G5.1

431.0G18.8 448.1G21.2

Review

(1) 1996ZAR/WES (2) 2005GIA

H–CHI2 DfH0(R)Z79.8G2.2 (333.9G9.2)

DfH0(R)ZK213.4G1 (K892.9G4.2)

1,1,2,2-Tetrafluoroethane CHF2CF2–H DfH0(R)ZK158.9G4.5 (K664.8G18.8)

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BDEs of C–H Bonds

1,2,2-Trifluoroethane

65

103.5G3.5

433.0G14.6

Review

1996ZAR/WES

102.0G3.5

426.8G14.6

Review

1996ZAR/WES

106.7G1.1

446.4G4.5

Kinetics

1974WU/ROD

99.5G1

416.3G4.2

Iodination

1977PIC/ROD

98.8G3

413.4G12.6

UV-FP

1983MAR/PAR

103.5G3.5

433.0G14.6

Review

1996ZAR/WES

CH2FCF2–H DfH0(R)ZK107.5G3.5 (K449.8G14.6)

1,2,2-Trifluoroethane CHF2CFH–H DfH0(R)ZK109G3.5 (K456.1G14.6)

1,1,1-Trifluoroethane CF3CH2–H DfH0(R)ZK123.6G2 (K517.1G8.4)

1,1-Difluoroethane CH3CF2–H DfH0(R)ZK72.3G2 (K302.5G8.4)

1,2-Difluoroethane CH2FCHF–H DfH0(R)ZK57.0G3 (K238.5G12.6)

1,1-Difluoroethane CHF2CH2–H DfH0(R)ZK68.3G3.5 (K285.8G14.6)

Fluoroethane

(1) 103.6G2

433.5G8.4

(1) Review

(1) 1996ZAR/WES

CH2FCH2–H

(2) 100.8G2

421.7G8.4

(2) Photobromin.

(2) 1996MIY/OZA

DfH0(R)ZK14.2G2 (K59.4G8.4)

Fluoroethane CH3CHF–H DfH0(R)ZK16.8G2

(1) 97.3G2

407.1G8.4

(1) Bromination

(1) 1987TSC/SAL(b)

(2) 98.2G2

410.9G8.4

(2) Photobromin.

(2) 1996MIY/OZA

(3) 99.6

416.9

(3) Derived

(3) 2004JAN/ROS

(K70.3G8.4)

(continued)

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66

Comprehensive Handbook of Chemical Bond Energies

Table 3.5 (continued) C–H BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) 1,1-Difluoro-1-chloro-ethane

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

104.9G1.8

439.0G7.5

Review

2005GIA

1-Chloro-2,2,2-trifluoro-ethane 101.8G1.5

425.9G6.3

Review

1982MCM/GOL

96.6G1.5

404.2G6.3

Review

1982MCM/GOL

2-Chloro-1,2,2-trifluoro-ethane 98.5G0.5

412.1G2.1

Pyrolysis

1998SKO/DYM

CF2ClCH2–H

CF3CHCl–H

1-Bromo-1-chloro-2,2,2trifluoroethane CF3CClBr–H DfH0(R)ZK120.5G2 (K504.2G8.4)

CClF2CHF–H DfH0(R)ZK107.7G3 (K450.6G12.6)

Pentachloroethane

(1) 95.8

400.8

(1) Photochlorin.

(1) 1969FRA/HUY

CCl3CCl2–H

(2) 95G2

397.5G8.4

(2) Shock tube

(2) 1976LEW

94G2

393.3G8.4

Shock tube

1976LEW

1,1-Dichloroethane

(1) 93.4G0.4

390.6G1.5

(1) PIMS detect.

(1) 1996SEE

CH3CCl2–H

(2) 95.1G1.2

397.9G5.0

(2) Kinetics

(2) 1999MIY/TSC

DfH0(R)Z8.4G1.3 (35.1G5.4)

1,1,2,2-Tetrachloroethane CHCl2CCl2–H DfH0(R)Z5.6G2 (23.4G8.4)

DfH0(R)Z10.2G0.4 (42.7G1.7)

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BDEs of C–H Bonds

67

Chloroethane

(1) 95.7

400.4

(1) Bromination

(1) 1987TSC/SAL(b)

CH3CHCl–H

(2) 98.2G2

410.9G8.4

(2) EI

(2) 1988HOL/LOS

DfH0(R)Z18.3G0.4 (76.6G1.5)

(3) 96.5G1

403.8G4.2

(3) Photobromin.

(3) 1990MIY/TSC

(4) 97.2G0.4

406.6G1.5

(4) PIMS detect.

(4) 1996SEE

Chloroethane

(1) 101.7G2

425.5G8.4

(1) EI

(1) 1988HOL/LOS

CH2ClCH2–H

(2) 100.7G1

421.3G4.2

(2) Photobromin.

(2) 1990MIY/TSC

(3) 101.1G0.6

423.1G2.4

(3) PIMS detect.

(3) 1998SEE

94.9G1.2

397.1G5.0

Kinetics

1999MIY/TSC

99.2G2

415.1G8.4

EI

1988HOL/LOS

DfH0(R)Z22.2G0.6 (93.0G2.4)

1,1-Dibromoethane CH3CBr2–H DfH0(R)Z33.5G1.3 (140.2G5.4)

Bromoethane CH2BrCH2–H DfH0(R)Z32.3 (135.1)

Bromoethane

(1) 96.4

403.3

(1) Bromination

(1) 1987TSC/SAL(b)

CH3CHBr–H

(2) 94.2G2

394.1G8.6

(2) EI

(2) 1988HOL/LOS

DfH0(R)Z30.3 (126.8)

(3) 97.2G1

406.7G4.2

(3) Photobromin.

(3) 1990MIY/TSC

Trifluoroethylene CF2aCF–H

111G2

464.4G8.4

Correlation

1981STE/ROW

1,1-Difluoroethylene

110G2

460.2G8.4

Correlation

1981STE/ROW

110G2

460.2G8.4

Correlation

1981STE/ROW

109G2

456.1G8.4

Correlation

1981STE/ROW

CF2aCH–H DfH0(R)ZK22.2G2 (K92.9G8.4)

(E)-1,2-Difluoroethylene CHFaCF–H DfH0(R)ZK12.1G2 (K50.6G8.4)

1,1-Difluoro-2-chloroethylene CF2aCCl–H

(continued)

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68

Comprehensive Handbook of Chemical Bond Energies

Table 3.5 (continued) C–H BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) (Z)-1,2-Chloro-2-fluoro-

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

108G2

451.9G8.4

Correlation

1981STE/ROW

107G2

447.7G8.4

Correlation

1981STE/ROW

Chloroethylene

(1) O103.6

O433.5

(1) PI MS

(1) 1989RUS/SEN

CH2aCCl–H

(2) 116.0G1.2

485.3G2.8

(2) UV-PI

(2) 1995SHE/QI

1,1,1,2,2,3,3-Heptafluoro propane

(1) 104G2

435.1G8.4

(1) Review

(1) 1982MCM/GOL

(2) 103.3

432.2

(2) Bromination

(2) 1983EVA/WEE

103.6G0.6

433.3G2.5

Kinetics

1983EVA/WEE

97.3G0.8

407.0G3.5

Derived

1998SEE

97.8G0.9

409.3G3.9

Derived

1998SEE

88.6G1.1

370.7G4.6

VLPP

1973ALF/GOL

88.6G1.1

370.7G4.6

VLPP

1973ALF/GOL

ethylene CFClaCCl–H

(E)-1,2-Dichloroethylene CHClaCCl–H DfH0(R)Z56.1G2 (234.7G8.4)

CF3CF2CF2–H

1,1,1,2,3,3,3Heptafluoropropane CF3CFHCF3

1-Chloropropane CH3CH2CHCl–H DfH0(R)Z13.5G0.8 (56.6G3.3)

1-Chloropropane CH2ClCH2CH3

1-Fluoropropene CH2aCH-CHF–H

1-Chloropropene CH2aCH-CHCl–H

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BDEs of C–H Bonds

1-Bromopropene

69

89.4G1.1

374.0G4.6

VLPP

1973ALF/GOL

116.5

487.4

TCT

1974KRE/PRI

115.0G2.6

481G11

FT-MS

2004PRA/FAT

76.7G3.1

481G13

FT-MS

2004PRA/FAT

78.2

327.2

AOP

1993BOR/ZHA(b)

82.3

344.3

AOP

1993BOR/ZHA(b)

CH2aCH-CHBr–H DfH0(R)Z48.1G1.1 (201.3G4.6)

Pentafluorobenzene H–C6F5 DfH0(R)ZK130.9G2 (K547.7G8.4)

1,2,3,4-Tetrafluobenzene F

H H

F F

F

1,2,3,4-Tetrafluobenzyl F H

F F

F

9-Pentafluorophenyl fluorine 9-C6F5FlH

Tri(2,3,5,6-tetrafluorophenyl) phenyl methane (p-HC6F4)3C–H

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70

3.6 3.6.1

Comprehensive Handbook of Chemical Bond Energies

Organic compounds containing heteroatom(s) C–H BDEs with a-OH, -OR, -C(O), -C(O)OH, -C(O)OR, -OC(O)R and -OOR

3.6.1.1 C–H BDEs with a-OH Table 3.6.1.1 C–H BDEs with a-OH BDEs The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

(boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Methanol H–CH2OH

(1) 95.9G1.5 (2) 96.0

401.2G6.3 401.7

(1) Iodination (2) SPST

(1) 1973ONE/BEN (2) 1981TSA

DfH0(R)ZK4.06G0.2

(3) 96.2G0.2

402.5G0.8

(3) PIMS detect.

(3) 1993RUS/BER

(4) 96.06G0.15

401.92G0.63

(4) Recommended

(4) 1994BER/ELL

(5) 96.2G0.3

402.5G1.3

(5) RF detect.

(5) 1996DOB/BER

95.6G1.2

400G5

PA

2001BOU/ROO

111.6G2.6

467G11

Derived from

1996NIST

(K17.0G0.7)

Ethenol CH2aCHOH

Ethenol

DfH0 in ref.

CH2aCHOH DfH0(R)Z28.9G2.6 (121G11)

Ethanol

(1) 93G1.0

389.1G4.2

(1) Iodination

(1) 1972ALF/GOL

CH3CH2OH

(2) 94.6

395.8

(2) SPST

(2) 1981TSA

DfH0(R)ZK13.3G0.8

(3) 94.8

396.6

(3) EI

(3) 1991HOL/LOS

(4) 95.9G1 (5) 95.7

401.2G4.2 400.3

(4) Review (5) Derived

(4) 1999ATK/BAU (5) 2004JAN/ROS

(K55.6G3.5)

Ethanol

(1) 101.3

423.8

(1) MS

(1) 1990TAK

CH3CH2OH

(2) 98G2

410.0G8.4

(2) PIMS detect.

(2) 1994RUS/BER

DfH0(R)ZK7.5G1.7

(3) 100.8G2

421.7G8

(3) Derived from

(3) 1996NIST

DfH0 in ref.

(K31G7)

Propanol CH3CH2CH2OH

(1) 93.7 (2) 95.5

392.0 399.5

(1) SPST (2) Correlation

DfH0(R)ZK19.4G1 (K81G8)

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(1) 1999TSA (2) 2005DEN/TUM

BDEs of C–H Bonds

Propanol

71

94.3G2

394.6G8.4

AE

1992HOL

97.1G2

406.3G8.4

AE

1992HOL

CH3CH2CH2OH DfH0(R)ZK18.8G2 (K78.7G8.4)

Propanol CH3CH2CH2OH DfH0(R)ZK16.0G2 (K66.9G8.4)

Propan-2-ol

(1) 91G1

380.7G4.2

(1) Review

(1) 1982MCM/GOL

(CH3)2CHOH

(2) 89.3G1.7

373.6G7.1

(2) PAC

(2) 1989KAM/GRI

DfH0(R)ZK23.0 (K96.4)

(3) 91.7G2

383.7G8.4

(3) AE

(3) 1992HOL

(4) 94.8

396.5

(4) Derived

(4) 2004JAN/ROS

(5) 93.3

390.5

(5) Correlation

(5) 2005DEN/TUM

94.3G2

394.6G8.4

AE

1992HOL

(1) 80.1 (2) 81.6G1.8

355.1 341.4G7.5

(1) Pyrolysis (2) Iodination

(1) 1973TRE (2) 1973ALF/GOL

DfH0(R)Z0G2 (0G8.4)

(3) 80.1

355.1

(3) PAC

(3) 1992ARN/CAL

(4) 85.1

356.2

(4) Correlation

(4) 2005DEN/TUM

Butyl alcohol C3H7CH2OH

94.9

397.2

Correlation

2005DEN/TUM

sec-Butyl alcohol

93.1

389.7

Correlation

2005DEN/TUM

Propan-2-ol (CH3)2CHOH DfH0(R)ZK23.0G1 (K96.2G4.2)

Allyl alcohol CH2aCHCH2OH

C2H5CH(CH3)OH

2-Methylpropan-2-ol

(1) 100G2

418.4G8.4

(1) Review

(1) 1982MCM/GOL

(CH3)3COH DfH0(R)ZK26.8G2

(2) 99.1 (3) 99.8

414.6 417.4

(2) PAC (3) Correlation

(2) 1989KAM/GRI (3) 2005DEN/TUM

94.5

395.2

Correlation

2005DEN/TUM

(K112.1G8.4)

2,2-Dimethylpropan-1-ol tert-C4H9CH2OH

(continued)

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72

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.1 (continued) C–H BDEs with a-OH

The broken bonds

BDEs (boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) Pentanol

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

93.5

391.4

Correlation

2005DEN/TUM

94.6

395.8

Correlation

2005DEN/TUM

94.5

395.5

Correlation

2005DEN/TUM

81.1

339.2

Correlation

2002DEN/DEN

69.0G1

288.7G4.2

PAC

1991CLA/CUL

79.0

330.7

Correlation

2005DEN/TUM

92.8

388.4

Correlation

2002DEN/DEN

(1) 87.6 (2) 79G2

366.4 330.5G8.4

Correlation

(1) 2005DEN/TUM (2) 2005BRA/GAL

85.1

356.0

Correlation

2002DEN/DEN

n-C5H11CH2OH

Nonanol n-C8H17CH2OH

Decanol n-C9H19CH2OH

2,3-Dimethylallyl alcohol CH2aC(CH3)CH(CH3)OH

Penta-1,4-dien-3-ol (CH2aCH)2CHOH

Cyclo-pent-2-en-1-ol H OH

Cyclo-hexanol OH H

Benzyl alcohol C6H5CH2OH DfH0(R)Z7G2 (29.3G8.4)

1-Phenylethanol PhMeCHOH

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BDEs of C–H Bonds

73

Diphenylmethn-1-ol

(1) 78

326

(1) PAC

(1) 1983ROT/SIM

Ph2CHOH

(2) 87G2

364G8

(2) Spectroscopy

(2) 1990POS/HAR

DfH0(R)Z36.4G1.5

(3) 75.4G1.5

315.5G6.3

(3) PAC

(3) 1992ARN/CAL

w92

w385

Electrochemical

1991MER/LIN

Ethane-1,2-diol (CH2OH)2

(1) 89.6G2.2 (2) 92.1

374.9G9.2 385.3

(1) PAC (2) AE

(1) 1989KAM/GRI (2) 1992HOL

DfH0(R)ZK52.6G2

(3) 95.6

400.0

(3) Correlation

(3) 2000DEN/DEN

96.6

404.2

Correlation

2005DEN/TUM

Butane-1,3-diol HOCH2CH2CH(CH3)OH

92.7

387.7

Correlation

2005DEN/TUM

Butane-2,3-diol

91.6

383.1

Correlation

2005DEN/TUM

(152.3G6.3)

Ethane-1,1-diol CH3CH(OH)2

(K220.1G8.4)

1,4-Butanediol HOCH2(CH2)2CH2(OH)

HOCH(CH3)CH(CH3)OH

3.6.1.2

C–H BDEs with a-OR

Table 3.6.1.2 C–H BDEs with a-OR BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Dimethyl ether

(1) 95.5

399.6

(1) PSD

(1) 1967LOU/LAI

CH3OCH3

(2) 93G1

389.1

(2) Review

(2) 1969GOL/BEN

DfH0(R)Z0G1 (0G4.2)

(3) 96.1

402.1

(3) Review

(3) 1999ATK/BAU

(4) 95.3

398.7

(4) Correlation

(4) 2000DEN/DEN

(5) 96.8

405.0

(5) Derived

(5) 2004JAN/ROS

(continued)

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74

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.2 (continued) C–H BDEs with a-OR BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

106G1

443.5G4.2

Kinetics

1995HSU/DEM

104G1

435.1G4.2

Kinetics

1995HSU/DEM

102G1

426.8G4.2

Kinetics

1995HSU/DEM

93.0

389.1

AE

1991HOL/LOS

Diethyl ether

(1) 91.7G0.4

383.7G1.7

(1) VLPP

(1) 1984KON/BEN

CH3CH2OCH2CH3

(2) 93

389.1

(2) PAC

(2) 1986BUR/MAJ

DfH0(R)ZK19.4G1

(3) 95.5G0.6

399.5G2.4

(3) Correlation

(3) 2000DEN/DEN

96.9

405.4

Re-anal.

1998BRO/BEC

Di-iso-propyl ether

(1) 93.9

392.9

(1) Re-anal.

(1) 1998BRO/BEC

(CH3)2CHOCH(CH3)2

(2) 93.4

390.8

(2) Correlation

(2) 2005DEN/TUM

Dibutyl ether

93.7

392.2

Correlation

2005DEN/TUM

96.1

402.1

Correlation

2002TUM/KRO

Difluoromethyl trifluoromethyl ether CHF2OCF3

Bis(difluoromethyl) ether CHF2OCHF2

Methyl trifluoromethyl ether CH3OCF3

Ethyl methyl ether CH3OCH2CH3 DfH0(R)ZK10.8G2 (K45.2G8.4)

(K81.2G4.2)

Ethyl tert-butyl ether CH3CH2O-tert-C(CH3)3

C3H7CH2OC4H9

Ditert-butyl ether (CH3)3COC(CH3)3

7366—CHAPTER 3—6/2/2007—13:17—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

75

89.9

376.3

Correlation

2000DEN/DEN

92.0

385.0

Correlation

2002TUM/KRO

Ethyl phenyl ether, substituted 85.5

357.7

Correlation

2005DEN/TUM

Correlation

2002TUM/KRO

Correlation

2002TUM/KRO

Correlation

2002TUM/KRO

Cyclo-hexyl methyl ether cyclo-C6H11–OMe

Methyl phenyl ether CH3OPh

p-n-Bu-C6H4OCH2CH3

Benzyl methyl ether, substituted H CH

Y

OCH3

YaH

85.8

359.0

3-Cl

86.3

360.9

4-Cl

85.9

359.5

4-Br

85.5

357.9

4-Me

85.4

353.3

4-Pr

84.4

353.2

4-MeO

84.7

354.5

85.8

359.0

83.7

350.0

Dibenzyl ether, substituted H CH2OCH

Y

YaH 4-MeO

Y

Diphenylmethyl methyl ether, substituted H

Y'

C

OCH3

Y

YaH

Y 0 aH

84.6

354.1

84.2

352.4

3-Cl

3-Cl

4-Br

4-Br

83.7

350.1

4-Me

4-Me

82.8

346.6

4-tBu

4-tBu

83.1

347.6

(continued)

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76

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.2 (continued) C–H BDEs with a-OR BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

4-MeO

4-MeO

81.9

342.8

4-MeC(O)O

4-MeC(O)O 84.5

353.5

Methods (reference in parentheses)

References

Dialkyloxymethenes (RO)2CH2 RaCH3

(1) 93.4

391.0

C2H5

(2) 93.2

390.1

n-C3H7

(2) 93.6

391.8

iso-C3H7

(1) 93.3

390.5

n-C4H9

(1) 93.0

389.1

iso-C4H9

(1) 93.1

389.5

sec-C4H9

(1) 93.6

391.5

CH2CH2CH(CH3)2

(1) 92.8

388.4

sec-C5H11

(1) 93.3

390.2

cyclo-C6H11

(1) 92.3

386.3

Correlation

(1) 2005DEN/TUM (2) 2002TUM/KRO

1,1-Di-alkyloxyethanes (RO)2CHCH3 RaCH3

91.1

381.2

C2H5

90.9

380.2

C3H7

90.7

379.6

iso-C3H7

91.0

380.7

n-C4H9

90.6

379.0

iso-C4H9

90.6

379.1

n-C5H11

90.4

378.3

iso-C5H11

90.4

378.3

cyclo-C6H11

90.9

380.2

90.5

378.8

C2H5

90.4

378.3

iso-C3H7

90.7

379.6

Correlation

2005TUM

Correlation

2005TUM

1,1-Di-alkyloxy-isobutanes (RO)2CHCH2CH2CH3 RaCH3

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BDEs of C–H Bonds

77

1,1-Di-alkyloxy-isobutanes (RO)2CHCH(CH3)2 RaCH3

(1) 91.2

381.4

C2H5

(1) 90.9

380.5

C3H7

(1) 90.7

379.5

iso-C3H7

(1) 91.2

381.4

n-C4H9

(1) 90.6

379.0

sec-C4H9

(1) 90.9

380.5

iso-C4H9

(2) 90.9

380.5

n-C5H11

(2) 90.4

378.3

iso-C5H11

(2) 90.7

379.6

90.0

376.5

Correlation

2005TUM

84.6

353.9

Correlation

2002TUM/KRO

4-Cl

84.7

354.3

4-Br

84.7

354.3

4-tBu

84.4

353.1

4-MeO

84.4

353.2

4-MeC(O)O

84.9

355.2

100.5G1.5

420.5G6.5

Pyrolysis

1984BAL/KEE

89.9

376.0

Correlation

2002TUM/KRO

1,1-Di-alkyloxy-toluene

Correlation

(1) 2005DEN/TUM

(2) 2005TUM

(C2H5O)2CHC6H5

Dimethoxyphenylmethane, substituted H C Y

OMe OME

YaH

Oxirane H

O

H 0

DfH (R)Z35.8G1.5 (149.8G6.3)

2-Methyl-oxirane O

H Me

(continued)

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78

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.2 (continued) C–H BDEs with a-OR BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) Tetrahydrofuran O

H H

DfH0(R)ZK4.3G1.5

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 92G1

384.9G4.2

(1) Kinetics

(1) 1982MCM/GOL

(2) 92.1G1.6

385.3G6.7

(2) PAC

(2) 1997LAA/MUL

(3) 92

384.9

(3) PAC

(3) 2000KRA/CIR

(4) 93.6G0.1

391.6G0.4

(4) Correlation

(4) 2002TUM/KRO

91.8

384.1

Correlation

2005DEN/TUM

Correlation

2005DEN/TUM

(K18.0G6.3)

Tetrahydrofurans, substituted O

H CH3

Tetrahydrofurans, substituted O

H OR

Ratert-Bu

91.2

381.4

n-C5H11

90.5

378.5

cyclo-C6H11

89.5

374.3

n-C8H17

89.7

375.3

92.6

387.5

Correlation

2002TUM/KRO

86.5G2

361.9G8.4

VLPP

1981STE

91.1

381.2

Correlation

2005DEN/TUM

89.2

373.4

2,5-Dimethyl-tetrahydrofuran O

H Me

H Me

2-Methyl furan O

CH2

H

1,3-Dioxolanes, substituted X

H

O

O

XaH Me

7366—CHAPTER 3—6/2/2007—13:19—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

79

n-Pr

89.0

372.5

iso-Pr

89.2

373.1

n-Bu

89.0

372.2

iso-Bu

88.7

371.3

n-C5H11

89.3

373.6

n-C6H13

88.8

371.6

Ph

89.2

373.2

1,3-Dioxolanes, substituted H O

Me

O

H

X

XaMe Et

96.7

404.8

91.2

381.7

Correlation

2005DEN/TUM

96.0

401.7

Correlation

2005DEN/TUM

Correlation

2005TUM

Correlation

2005DEN/TUM

Tetrahydropyran H

O

H

2-Alkyl-2HK3,4,5,6-tetra-hydropyrans H O

O R

RaC3H7

92.3

386.0

iso-C3H7

92.0

385.0

tert-C4H9

92.3

386.0

C6H11

91.3

381.8

C8H17

90.9

380.5

CH(C3H7)(C4H9)

90.9

380.5

cyclo-C6H11

90.4

378.3

CH2CH2-cyclo-C6H11

91.7

383.7

CH2-cyclo-2-oxy-C4H7

90.1

377.1

1,3-Dioxanes, substituted O O

XaH Me

X H

92.7

388.0

90.3

378.0

(continued)

7366—CHAPTER 3—6/2/2007—13:19—JEBA—15359—XML MODEL B – pp. 19–145

80

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.2 (continued) C–H BDEs with a-OR BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Et

91.2

381.7

n-Pr

90.3

377.7

n-Bu

90.1

377.0

n-C6H13

90.0

376.5

Ph

90.4

378.4

Methods (reference in parentheses)

References

1,3-Dioxanes, substituted Me O

X

O

H

XaH Me

91.7

383.6

90.6

378.9

Correlation

2005DEN/TUM

94.7

396.2

Correlation

2005DEN/TUM

Correlation

2005DEN/TUM

Correlation

2005DEN/TUM

1,3-Dioxanes, substituted H O

H

O

1,3-Dioxanes, substituted Me

O

X

Me

O

H

XaH

92.9

388.7

Me

90.9

380.3

n-Pr

90.7

379.4

iso-Pr

90.8

380.1

n-Bu

90.6

379.1

iso-Bu

90.5

378.5

n-C6H13

90.4

378.1

93.2

389.8

1,3-Dioxanes, substituted O O

Me

H H

Me

7366—CHAPTER 3—6/2/2007—13:19—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

81

1,3-Dioxanes, substituted

Et

O

Me

O

H

93.1

389.7

Correlation

2005DEN/TUM

92.8

388.4

Correlation

2005DEN/TUM

91.2

381.4

Correlation

2005DEN/TUM

91.2

381.4

Correlation

2005TUM

H

(1) 96

401.7

(1) PAC

(1) 2000KRA/CIR

H

(2) 97.0

405.7

(2) Correlation

(2) 2005DEN/TUM

89.2

373.0

Correlation

2002TUM/KRO

91.8

384.3

Correlation

2005DEN/TUM

90.9

380.2

Me

1,3-Dioxanes, substituted Me Me

O

H

O

H

Me

1,3-Dioxanes, substituted

Me

O

Et

O

H

Me

3,3-Diethyl-1,3-dioxane H

O O

C2H5

H

C2H5

1,4-Dioxane O O

DfH0(R)ZK31.5G3 (K131.8G12.6)

2,5-Dimethyl-1,4-dioxane H

O

H

Me

Me

O

Dicyclohexyloxymethane O H

XaH Me

O X

(continued)

7366—CHAPTER 3—6/2/2007—13:19—JEBA—15359—XML MODEL B – pp. 19–145

82

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.2 (continued) C–H BDEs with a-OR BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Tetrahydropyrans, substituted O H O

90.1

377.1

Correlation

2005DEN/TUM

91.7

383.7

Correlation

2005DEN/TUM

90.9

380.5

Correlation

2005DEN/TUM

93.4

390.8

Correlation

2005DEN/TUM

89.7

375.5

92.1

385.5

Correlation

2005DEN/TUM

H

O

Tetrahydropyrans, substituted

H O

O

OCH2CH2O

Tetrahydropyrans, substituted H O

OCH

n-Pr n-Bu

Tetraoxaspiro[5,5]undecane, substituted O

X2

O

X1aH,

O

X1

O

H

X2aH

Me

Me

1,3-Dioxepanes, substituted O

H

O

X

XaH Me

91.0

380.8

Et

90.6

379.2

n-Pr

90.4

378.1

7366—CHAPTER 3—6/2/2007—13:20—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

83

iso-Pr

90.2

377.4

n-C6H13

90.4

378.1

95.8

400.9

1,3,6-Trioxocane O

O

O

3.6.1.3

H

Correlation

2005DEN/TUM

H

C–H BDEs with a-C(O)

Table 3.6.1.3 C–H BDEs with a-C(O) BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZ

reference in parentheses)

dissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Formaldehyde

(1) 88.8G0.5

371.5G2.1

(1) EI

(1) 1985TRA

HC(O)–H

(2) 88.0

368.2

(2) Photolysis

(2) 1987CHU/FOL

DfH0(R)Z9.96G0.20 (41.67G0.84)

(3) 88.04G0.16 (4) 88.15G0.01

368.40G0.67 368.80G0.03

(3) Recommended (4) Photolysis

(3) 1994BER/ELL (4) 1996TER/KAB

(5) 88.64G0.1

370.86G0.28

(5) Laser FP

(5) 1997BEC/CAR

Formyl fluoride

(1) 99.92G0.06

418.07G0.24

(1) UV Photolysis

(1) 1997REE/KON

FC(O)–H

(2) 101.1

423.0

(2) Derived from

(2) 1998CHA

DfH0(R)ZK38.5 (K161.2)

Ethanal or acetadehyde CH3C(O)–H DfH0(R)ZK2.5G0.4 (K10.3G1.8)

2-Ethylbutanal

DfH0 in ref.

(1) 87.3G2.0 (2) 89.3G0.5

365.3G8.4 373.6G2.1

(1) EI (2) PIMS detect.

(1) 1984HOL/LOS (2) 1992NII/GUT

(3) 89.4G0.3

374.0G1.3

(3) Recommended

(3) 1994BER/ELL

(4) 88.7

371.1

(4) SPST

(4) 1999TSA

(5) 89.7

375.4

(5) Derived

(5) 2004JAN/ROS

87.8

367.2

Correlation

2002TUM/KRO

89.2

373.3

Correlation

2002TUM/KRO

Et2CHC(O)–H

Decanal CH3(CH2)8C(O)–H

(continued)

7366—CHAPTER 3—6/2/2007—13:20—JEBA—15359—XML MODEL B – pp. 19–145

84

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.3 (continued) C–H BDEs with a-C(O) BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZ

reference in parentheses)

dissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Furfurol O

H

C(O) H

90.5

378.7

Correlation

Benzaldehyde

(1) 86.9G1.0

363.6G4.2

(1) Iodination

(1) 1982MCM/GOL

C6H5C(O)–H

(2) 88.7G2.6

371.1G10.9

(2) PAC

(2) 1989SIM/GRI

DfH0(R)Z27.8G2.6

2000DEN/DEN

(3) 88.9

372.0

(3) Electrochemical

(3) 1995LUN/DAA

(4) 83.2

348.0

(4) Correlation

(4) 2002TUM/KRO

(5) 91.6

383.1

(5) Derived

(5) 2004JAN/ROS

Ya3-Cl

84.5

353.6

Correlation

2002TUM/KRO

(116.3G10.9)

Benzaldehyde, substituted O Y

C H

4-Cl

84.2

352.3

3-Br

84.6

353.8

3-Me

82.9

347.0

4-Me

82.6

345.8

3-t-Bu

82.6

345.4

4-t-Bu

80.6

337.1

3-MeO

83.9

350.9

4-MeO

82.8

346.4

3-NO2

82.2

343.7

4-NO2

81.3

340.4

4-PhO

83.0

347.1

86.5

362.0

Correlation

2002TUM/KRO

86.7

362.9

Correlation

2002TUM/KRO

2-Pyenylethanal PhCH2C(O)–H

2-Methy-2-phenylpropanal PhC(CH3)2C(O)–H

7366—CHAPTER 3—6/2/2007—13:20—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

85

Ketene

(1) 105.9G2.1

443.1G8.8

(1) PES

(1) 1983OAK/JON

H–CHaCaO

(2) 105.3G2.1

440.6G8.8

(2) Recommend.

(2) 1994BER/ELL

88.4

370.0

Correlation

2002TUM/KRO

2,3,4,5,6-Pentahydroxyhexanal 88.8

371.4

Correlation

2005DEN/TUM

90.9

380.3

Derived

2004JAN/ROS

Acetadehyde

(1) 95.1

397.9

(1) GPA

(1) 1977CUM/KEB

CH3C(O)H

(2) 94.3G2.2

394.5G9.2

(2) Recommended

(2) 1994BER/ELL

DfH0(R)Z2.5G2.2

(3) 94.2

394.3

(3) Correlation

(3) 2002TUM/KRO

Acetyl fluoride CH3C(O)F

93.2G1.5

389.9G6.3

Derived from DfH0(R) in ref.

1996NIST

Acetyl chloride

%101.2

%423.4

IR CL

1998SRI/ARU

91.7

383.7

GPA

1977CUM/KEB

DfH0(R)Z42.4G2.2 (177.5G8.8)

2,3,4,5-Tetrahydroxypentanal CH2(OH)(CHOH)3C(O)H

CH2(OH)(CHOH)4C(O)H

Methylketene CH3CHC(O)

(10.5G9.2)

CH3C(O)Cl

Propanal CH3CH2C(O)H

Acetone

(1) 98.3G1.8

411.3G7.5

(1) Bromination

(1) 1970KIN/GOL

CH3C(O)CH3

(2) 97.0

405.8

(2) GPA

(2) 1977CUM/KEB

DfH0(R)ZK8.1G0.7

(3) 95.9G0.7

401.2G2.9

(3) Derived from

(3) 2001BOU/CHA

DfH0(R) in ref.

(K33.9G3) (4) 94

393.3

(4) AOP

(4) 2002ALN/ZHA

(5) 96.0G2.2

401.7G9.2

(5) GPA

(5) 2003REE/HAR

(continued)

7366—CHAPTER 3—6/2/2007—13:21—JEBA—15359—XML MODEL B – pp. 19–145

86

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.3 (continued) C–H BDEs with a-C(O) BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZ

reference in parentheses)

dissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

96.2

402.5

GPA

1977CUM/KEB

Ethyl methyl ketone CH3C(O)CH2CH3

96.5

403.8

GPA

1977CUM/KEB

Ethyl methyl ketone

(1) 92.3G1.7

386.2G7.1

(1) Iodination

(1) 1970SOL/GOL

MeC(O)CH2Me

(2) 93.2

389.9

(2) GPA

(2) 1977CUM/KEB

DfH0(R)ZK16.8G1.7

(3) 93.8

392.6

(3) Correlation

(3) 2002TUM/KRO

(4) 91.3

382.1

(4) Derived

(4) 2004JAN/ROS

iso-Propyl methyl ketone MeC(O)CHMe2

91.7

383.8

Correlation

2002TUM/KRO

Allyl methyl ketone

82.8

346.6

Correlation

2002DEN/DEN

92.9

388.7

Correlation

2002TUM/KRO

Methyl tert-butyl ketone

(1) 96.5

403.8

(1) GPA

(1) 1977CUM/KEB

CH3C(O)-tert-Bu

(2) 94

393.3

(2) AOP

(2) 1990BOR/HAR

DfH0(R)ZK27.6G3

(3) 93.9

392.9

(3) AOP

(3) 2002ALN/ZHA

Diethyl ketone

(1) 93.4

390.8

(1) GPA

(1) 1977CUM/KEB

CH3CH2C(O)CH2CH3

(2) 88

368.2

(2) AOP

(2) 1990BOR/HAR

(3) 94.8G0.7 (4) 88.4

396.5G2.8 369.9

(3) Correlation (4) AOP

(3) 2002TUM/KRO (4) 2002ALN/ZHA

94.3G0.8

394.6G3.3

Correlation

2002TUM/KRO

1,1,1-Trifluoroacetone CF3C(O)CH3

(K70.3G7.1)

MeC(O)CH2CHCH2

iso-Butyl methyl ketone MeC(O)CH2CH(CH3)2

(K115.5G12.6)

Dipropyl ketone C2H5CH2C(O)C3H7

7366—CHAPTER 3—6/2/2007—13:21—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

87

Di-iso-propyl ketone

(1) 85

355.6

(1) AOP

(1) 1990BOR/HAR

Me2CHC(O)CHMe2

(2) 92.6

387.5

(2) Correlation

(2) 2005DEN/TUM

94.6G0.6

395.8G2.4

Correlation

2002TUM/KRO

(1) 96.8

405.0

(1) GPA

(1) 1977CUM/KEB

(2) 93

389.1

(2) AOP

(2) 1990BOR/ZHA

(3) 93.3 (4) 96.3G0.9

390.4 402.8G3.6

(3) AOP (4) Correlation

(3) 2002ALN/ZHA (4) 2002TUM/KRO

p-NO2

(5) 89

372.4

(5) AOP

(5) 1995ZHA/BOR

p-CN

(6) 93.4

390.8

(6) AOP

(6) 2002ALN/ZHA

p-MeO

(6) 93.3

390.4

93.8

392.5

AOP

2002ALN/ZHA

94

393.3

AOP

2002ALN/ZHA

94

393.3

AOP

2002ALN/ZHA

93.2

390

AOP

1997CHE/LIU

AOP

(1) 1992BOR/JI

DfH0(R)ZK41.5G5 (K173.6G21)

Dibutyl ketone C3H7CH2C(O)C4H9

Methyl phenyl ketone, substituted O H

CH2

C

Y

YaH, DfH0(R)Z20.2G3 (84.5G12.6)

Methyl trimethylphenyl ketone CH3C(O)(C6H2(Me)3)

Methyl naphthyl-1 ketone CH3C(O)(1-naphthyl)

Methyl anthracenyl-9 ketone CH3C(O)(9-anthracenyl)

Methyl phenyl ketone bromide PhC(O)CH2HCBrK

Benzyl methyl ketone

(1) 82.3

344.3

MeC(O)CH2Ph

(2) 82.6

345.6

(2) 2002ALN/ZHA

(continued)

7366—CHAPTER 3—6/2/2007—13:21—JEBA—15359—XML MODEL B – pp. 19–145

88

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.3 (continued) C–H BDEs with a-C(O) BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZ

reference in parentheses)

dissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ethyl phenyl ketone

(1) 88

368.2

(1) AOP

(1) 1990BOR/HAR

MeCH2C(O)Ph

(2) 92.9

388.7

(2) Re-anal.

(2) 1998BRO/BEC

DfH0(R)Z9.9G5

(3) 94.3

394.4

(3) Correlation

(3) 2002TUM/KRO

94.2

394.3

Correlation

2002TUM/KRO

(41.4G20.9)

Propyl phenyl ketone EtCH2C(O)Ph

iso-Propyl phenyl ketone

(1) 86

359.8

(1) AOP

(1) 1990BOR/HAR

(CH3)2CHC(O)Ph

(2) 89.9

376.1

(2) Re-anal.

(2) 1998BRO/BEC

sec-Butyl phenyl ketone

(3) 87.2

365.0

(3) Correlation

(3) 2000DEN/DEN

(4) 92.1

385.3

(4) Correlation

(4) 2002TUM/KRO

92.1

385.2

Correlation

2002TUM/KRO

98.8

413.3

Correlation

2002TUM/KRO

94.2

394.3

Correlation

2002TUM/KRO

AOP

(CH3)2CHCH2C(O)Ph

tert-Butyl phenyl ketone (CH3)3CC(O)Ph

Nonanyl phenyl ketone CH3(CH2)7CH2C(O)Ph

Benzyl phenyl ketone

(1) 82.5

345.2

PhCH2C(O)Ph

(2) 82.7

346.0

(1) 1990BOR/HAR (2) 2002ALN/ZHA

Dibenzyl ketone

(1) 83

347.3

(1) AOP

(1) 1990BOR/HAR

PhCH2C(O)CH2Ph

(2) 87.1

364.5

(2) Correlation

(2) 2000DEN/DEN

88.5

370.3

AOP

1990BOR/HAR

DfH0(R)Z32.1G3 (134.3G12.6)

Propylphenyl phenyl ketone PhCH2CH2C(O)Ph

7366—CHAPTER 3—6/2/2007—13:22—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

Anthracenyl-2 phenyl ketone

89

81.6

341.4

AOP

2002ALN/ZHA

84.4

353.1

AOP

2002ALN/ZHA

83

347.3

AOP

2002ALN/ZHA

82.7

346.0

AOP

2002ALN/ZHA

80.7

337.6

AOP

2002ALN/ZHA

Phenyl phenathrenyl-2 ketone 83.2

348.1

AOP

2002ALN/ZHA

348.5

AOP

2002ALN/ZHA

351.0

AOP

2002ALN/ZHA

85.7

358.6

AOP

2002ALN/ZHA

83.6

349.8

AOP

2002ALN/ZHA

(1) 82

343.1

AOP

(1) 1990BOR/HAR

(2) 82.2

343.9

PhC(O)CH2Anth(2)

Anthracenyl-9 phenyl ketone PhC(O)CH2Anth(9)

Naphthyl-1 phenyl ketone PhC(O)CH2Naphth(1)

Naphthyl-2 phenyl ketone PhC(O)CH2Naphth(2)

Phenyl pyrenyl-1 ketone PhC(O)CH2Py(1)

PhC(O)CH2Phen(2)

Phenyl phenathrenyl-3 ketone 83.3 PhC(O)CH2Phen(3)

Phenyl phenathrenyl-9 ketone 83.9 PhC(O)CH2Phen(9)

Phenyl pyridyl ketone PhC(O)CH2Py

Chromium tricarbonyl complexes PhC(O)CH2Ph(Cr(CO)3)

Diphenylmethyl methyl ketone

(2) 2002ALN/ZHA

Ph2CHC(O)CH3

(continued)

7366—CHAPTER 3—6/2/2007—13:22—JEBA—15359—XML MODEL B – pp. 19–145

90

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.3 (continued) C–H BDEs with a-C(O) BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZ

reference in parentheses)

dissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

83

347.3

AOP

1990BOR/HAR

81

338.9

AOP

1990BOR/HAR

337.2

AOP

1994BOR/ZHA

80.6

337.2

AOP

1994BOR/ZHA

98.4

411.6

Correlation

2002TUM/KRO

Pentane-2,4-dione

(1) 91.6

383.3

(1) AOP

(1) 1995BOR/ZHA

CH2(COMe)2

(2) 87.7 (3) 95.4G0.6

366.9 399.1G2.7

(2) Re-anal. (3) Correlation

(2) 1998BRO/BEC (3) 2002TUM/KRO

AOP

(1) 1990BOR/HAR

Diphenylmethyl phenyl ketone Ph2CHC(O)Ph

2-Methoxy-1-phenylethan-1one PhC(O)CH2OMe

2-Ethoxy-1-phenylethan-1-one 80.6 PhC(O)CH2OEt

1-Phenyl-2-phenoxyethan-1one PhC(O)CH2OPh

Butane-2,3-dione CH3C(O)C(O)CH3

1,3-Diphenylpropane-1,3dione

(1) 93

389.1

(2) 92

384.9

92

384.9

AOP

1990BOR/HAR

84.7

354.4

Re-anal.

1998BRO/BEC

(2) 1991BOR/HAR

CH2(COPh)2

1-Phenylbutane-1,3-dione PhC(O)CH2COMe

3-Methylpentane-2,4-dione (Me)CH(COMe)2

7366—CHAPTER 3—6/2/2007—13:22—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

91

b-Propiolactone O CH2

H

99.4G2.3

415.9G9.6

FT-ICR

2002KAR/JAN

(1) 88

368.2

(1) AOP

(1) 1991BOR/GAL

(2) 95.9

401.2

(2) Correlation

(2) 2002TUM/KRO

(3) 94.8G2.3

396.6G9.6

(3) FT-ICR

(3) 2002KAR/JAN

(1) 89

372.4

94.2

394.1

Correlation

2002TUM/KRO

93.1

389.6

Correlation

2002TUM/KRO

95

397.5

AOP

1991BOR/JI

CH2 H

Cyclo-pentanone, substituted O

H

X

H

X'

XaH, X 0 aH DfH0(cyclopentanonyl)Z K10G3 (K41.8G12.6) Me

Me

Cyclo-hexanone H H O

2,2-Dimethyl-2HK3,5,6trihydropyran-4-one H2C H2C

O CO

Me Me H H

1,7,7-Trimethyl bicyclo(2.2.1) heptane-2-one H3C

CH3 H H CH3

O

(continued)

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92

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.3 (continued) C–H BDEs with a-C(O) BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZ

reference in parentheses)

dissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Indan-2-one H

H

79.1

331.0

AOP

1994ZHA/BOR(e)

82.3

344.3

AOP

2002ALN/ZHA

82.5

345.2

AOP

2002ALN/ZHA

80

334.7

AOP

2002ALN/ZHA

O

1-Acenaphthenone H

O

H

2-Aceanthrenone H

O

H

1-Aceanthrenone O

H H

7366—CHAPTER 3—6/2/2007—13:23—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

3.6.1.4

93

C–H BDEs with a-C(O)OH

Table 3.6.1.4 C–H BDEs with a-C(O)OH BDEs The broken bonds

(boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Formic acid

(1) 98

410.0

(1) Correlation

(1) 1973MCK/DUN

H–C(O)OH

(2) 93.2

389.9

(2) EI

(2) 1991HOL/LOS

DfH0(R)ZK46.5G0.7

(3) O89.5

O374.5

(3) Review

(3) 1994BER/ELL

(4) 96.6

404.2

(4) Review

(4) 1994BER/ELL

(5) R96.1G0.7

R402.1G2.9

(5) PI, revised

(5) 2000RUS/LIT

Acetic ion

(1) 91.9G1.7

384.5G7.1

(1) PAC

(1) 1989KAM/GRI

CH3C(O)OK

(2) 96.1

402

(2) Derived

(2) 1994YU/RAU

(3) 93.7G4

392.0G16.7

(3) CID

(3) 1994WEN/SQU(b)

(4) w95

w397.5

(4) Review

(4) 2002REE/KAS

Acetic acid

(1) 96.1

402.1

(1) Correlation

(1) 1984NON/WAL

CH3C(O)OH

(2) 93.9G2

392.9G8.4

(2) AE

(2) 1991HOL/LOS (3) 1994WEN/SQU(b)

(K194.6G2.9)

DfH0(R)ZK60.2G2.9 (K251.9G12.0)

(3) 95.3G2.9

398.7G12.1

(3) CID

(4) 95.9

401.3

(4) Correlation

(4) 2000DEN/DEN

(5) 98.7G0.8

413.0G3.3

(5) Calorimetry

(5) 2001LAG/DIO

Chloroacetic acid

(1) 95.3

398.9

(1) Correlation

(1) 2002TUM/KRO

ClCH2C(O)OH

(2) 91.0G0.9

380.7G3.9

(2) Combination

(2) 2002LAG/DIO

Correlation

2002TUM/KRO

Correlation

2005DEN/TUM

Carboxylic acid CH3(CH2)nCH2C(O)OH nZ0

95.3

398.8

1

95.3

398.7

2

95.5

399.4

3

95.5

399.4

4

95.4

399.1

7

95.4

399.1

92.8

388.3

1-Methyl propanoic acid (CH3)2CHC(O)OH

(continued)

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94

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.4 (continued) C–H BDEs with a-C(O)OH BDEs The broken bonds

(boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) 2,2-Dimethl-propanioc acid

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

99.2

415.2

Correlation

2002TUM/KRO

(1) 93.2

390.0

Correlation

(1) 2002TUM/KRO

(2) 95.4

399.0

86.0

359.8

Correlation

2005DEN/TUM

92.8

388.2

Correlation

2005DEN/TUM

88.4

370.0

Correlation

2002TUM/KRO

88.4

370.0

Correlation

2005DEN/TUM

87.7

367.0

Correlation

2002TUM/KRO

95.1

397.8

Correlation

2002TUM/KRO

(CH3)3CC(O)OH

Cyclo-butalcarboxylic acid H

(2) 2005DEN/TUM

C(O)OH

Cyclo-butalcarboxylic acid H C(O)OH

H

Cyclo-hexacarboxylic acid H C(O)OH

Cyclo-hex-1-enecarboxylic acid H H

C(O)OH

Cyclo-1-Ene-1,2-dicarrboxylic acid H H C(O)OH C(O)OH

Benzenacetic acid PhCH2C(O)OH

Glycolic acid (OH)CH2C(O)OH

7366—CHAPTER 3—6/2/2007—13:23—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

2-Hydroxyacetic acid

95

92.3

386.0

Correlation

2005DEN/TUM

89.7

375.3

Correlation

2002TUM/KRO

95.6

400.1

Correlation

2002TUM/KRO

95.1

397.8

Correlation

2002TUM/KRO

94.0

393.1

Correlation

2005DEN/TUM

CH3CH(OH)C(O)OH

2-Oxoacetic acid H–(O)CC(O)OH

Propanedioic acid CH2(C(O)OH)2

Butanedioic acid HO(O)CCH2CH2C(O)OH

Carboxylic acid, substituted t-BuOC(O)(CH2)nCH2C(O)OH nZ1 2

93.5

391.0

3

93.6

391.5

4

93.5

391.3

7

93.5

391.3

93.9

392.7

Correlation

2005DEN/TUM

2,3-Dihydroxybutanedioic acid (HOCHC(O)OH)2

Methyl formate

(1) 92.7G1

387.9G4.2

(1) Kinetics

(1) 1969SOL/BEN

H–C(O)OCH3

(2) 95.4G2

399.2G8.4

(2) EI

(2) 1991HOL/LOS

DfH0(R)ZK38.6 (K161.5)

(3) 95.1

398.0

(3) Derived

(3) 2004JAN/ROS

7366—CHAPTER 3—6/2/2007—13:24—JEBA—15359—XML MODEL B – pp. 19–145

96

3.6.1.5

Comprehensive Handbook of Chemical Bond Energies

C–H BDEs with a-C(O)OR, -OC(O)R and -OOR

Table 3.6.1.5 C–H BDEs with a-C(O)OR, -OC(O)R and -OOR BDEs The broken bonds

(boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Acetic acid methyl ester

(1) 93.9

392.9

(1) EI

(1) 1991HOL/LOS

CH3C(O)OCH3

(2) 97.1G2.5

406.3G10.5

(2) FT-ICR

(2) 2002KAR/JAN

DfH0(R)ZK56.6G2

(3) 96.6

404.0

(3) Correlation

(2) 2002TUM/KRO

96.7

404.6

Correlation

2000DEN/DEN

(K236.8G8.4)

Acetic acid methyl ester CH3C(O)OCH3

Acetic acid ethyl ester

(1) 96

401.7

(1) AOP

(1) 1995BOR/ZHA

CH3C(O)OCH2CH3

(2) 95.5

399.5

(2) Correlation

(2) 2000DEN/DEN

95.6

400.0

Re-anal.

1998BRO/BEC

94.4

394.9

Correlation

2002TUM/KRO

94.4

394.9

Correlation

2002TUM/KRO

93.7

392.1

Correlation

2005DEN/TUM

94.3

394.5

Correlation

2002TUM/KRO

93.7

392.1

Correlation

2002TUM/KRO

DfH0(R)ZK62.2G3 (K260.2G12.6)

Ethyl propanoate CH3CH2C(O)OC2H5

Methyl bytanoate CH3CH2CH2C(O)OCH3

Methyl pebtanoate CH3(CH3)2CH2C(O)OCH3

Ethyl butylanoate CH3(CH3)3C(O)OCH2CH3

Ethyl pentanoate CH3(CH3)4C(O)OCH2CH3

Propyl pebtanoate CH3(CH3)4C(O)OCH2CH2CH3

7366—CHAPTER 3—6/2/2007—13:24—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

Acetic acid isopropyl ester

97

93.8

392.3

Correlation

2000DEN/DEN

92.6

387.4

Re-anal.

1998BRO/BEC

92.7

387.9

Correlation

2002TUM/KRO

99.2

415.0

Correlation

2002TUM/KRO

93.7

391.9

Correlation

2002TUM/KRO

100.0

418.4

Correlation

2002TUM/KRO

100.2G1.3

419.2G5.4

Iodination

1973ALF/GOL

CH3C(O)OCH(CH3)2

Ethyl 2-methylpropanoate (CH3)2CHC(O)OC2H5

iso-Propyl pebtanoate CH3(CH3)4C(O)OCH(CH3)2

tert-Butyl-2,2-dimethylpropanoate (CH3)3C(O)OC(CH3)3

Octyl pentanoate C4H9C(O)OCH2C7H15

Methyl benzoate PhC(O)OCH3

Acetic acid phenyl ester CH3C(O)OPh DfH0(R)ZK16.7 (K69.9)

Ethyl 2-phenylacetate

(1) 84.0

351.5

(1) AOP

(1) 1994ZHA/BOR(e)

PhCH2C(O)OEt

(2) 88.6

370.7

(2) Re-anal.

(2) 1998BRO/BEC

Ethyl methyl butane-1,4-dioate

(1) 92.9

388.7

(1) AOP

(1) 1995BOR/ZHA

CH2(COMe)(C(O)OEt)

(2) 94.8

396.5

(2) Correlation

(2) 2005DEN/TUM

Acetic acid anhydride

97.0

406.0

Correlation

2000DEN/DEN

96.5

403.8

Correlation

2000DEN/DEN

CH3C(O)OC(O)CH3

Oxalic acid dimethyl ester (CH3C(O)O)2

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.5 (continued) C–H BDEs with a-C(O)OR, -OC(O)R and -OOR BDEs The broken bonds

(boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) Diethyl ethane-1,2-dioate

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

94.7

396.2

Correlation

2002TUM/KRO

(CH3CH2OC(O))2

Malonic acid dimethyl ester

(1) 90.5

378.7

(1) AOP

(1) 1991BAU/FAS(c)

CH2(MeOC(O))2

(2) 93.6

391.7

(2) Correlation

(2) 2002TUM/KRO

Ethyl 3-oxobutanoate

94.8

396.5

Correlation

2002TUM/KRO

92.3

386.2

AOP

1996ZHA/BOR

96.7

404.8

Correlation

2002TUM/KRO

CH2(C(O)Me)(C(O)OEt)

Ethyl methyl propane-1,3-dioate CH2(C(O)OEt)(C(O)OMe)

Dimethyl bytane-1,4-dioate (CH2C(O)OCH3)2

Oxilic axcid diethyl ester

(1) 95

397.5

(1) AOP

(1) 1993ZHA/BOR

CH2(C(O)OC2H5)2

(2) 94.8

396.5

(2) Correlation

(2) 2000DEN/DEN

Dimethyl pentane-1,5-dioate

94.0

393.1

Correlation

2002TUM/KRO

94.0

393.2

Correlation

2002TUM/KRO

93.8

392.6

Correlation

2002TUM/KRO

(1) 90.5

378.7

AOP

(2) 90.8

379.9

CH2(CH2C(O)OCH3)2

Dimethyl heptane-1,7-dioate CH2(CH2CH2C(O)OCH3)2

Dimethyl nonane-1,9-dioate CH2(CH2CH2CH2C(O)OCH3)2

Dimethyl 2-methyl propane-1,3-dioate MeCH(C(O)OMe)2

7366—CHAPTER 3—6/2/2007—13:24—JEBA—15359—XML MODEL B – pp. 19–145

(1) 1994ZHA/BOR(e) (2) 1996ZHA/BOR

BDEs of C–H Bonds

Ethyl methyl 2-ethyl

99

89.6

374.9

AOP

1996ZHA/BOR

91.5

382.8

AOP

1996ZHA/BOR

94.7

396.2

Correlation

2002TUM/KRO

94.5

395.5

Correlation

2002TUM/KRO

93.6

391.7

Correlation

2002TUM/KRO

93.5

391.2

Correlation

2002TUM/KRO

93.5

391.1

Correlation

2002TUM/KRO

85.3

356.9

AOP

1993ZHA/BOR

85.6

358.2

Re-anal.

1998BRO/BEC

propane-1,3-dioate EtCH(C(O)OEt)(C(O)OMe)

Diethyl 2-ethyl propane-1,3-dioate EtCH(C(O)OEt)2

Dimethylethyl ethane-1,2-dioate (Me2CHOC(O))2

Dimethylethyl butane 1,4-dioate (Me2CHOC(O)CH2)2

Dimethylethyl pentane 1,5-dioate CH2(Me2CHOC(O)CH2)2

Dimethylethyl heptane 1,7-dioate CH2(Me2CHOC(O)CH2CH2)2

Dimethylethyl decane 1,10-dioate (Me2CHOC(O)(CH2)4)2

Diethoxy 2phenylpropane-1,3-dione PhCH(C(O)OEt)2

Ethyl 2-phenylpropanoate PhCHMe(C(O)OEt)

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 3.6.1.5 (continued) C–H BDEs with a-C(O)OR, -OC(O)R and -OOR BDEs The broken bonds

(boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

Diethyl 2-(1,1-dimethyl-1silaethyl) 87.3

kJ/mol

Methods (reference in parentheses)

References

365.3

AOP

1996ZHA/BOR

85.2

365.5

AOP

1996ZHA/BOR

98.4

411.7

Derived

2004JAN/ROS

97.1

406.1

Derived

2004JAN/ROS

89.2G2.3

373.2G9.6

FT-ICR

2002KAR/JAN

92.8G2.4

388.3G10.0

FT-ICR

2002KAR/JAN

92.6

387.4

AOP

1994ZHA/BOR(e)

87.5

366.1

propane-1,3-dioate Me3SiCH2CH(CO2Et)2

Ethyl methyl 2-(1,1-dimethyl1silaethyl) propane-1,3-dioate Me3SiCH(CO2Et)(CO2Me)

Methyl hydroperoxide CH3OOH DfH0(R)Z15.8 (66.1)

Ethyl hydroperoxide CH3CH2COOH DfH0(R)Z6.4 (26.9)

d-Valerolactone H2 H2 C C CH 2 CO H C O H

3-Caprolactone H2C CH2 CH2 CH2 H CO O H

2,2-Dimethyl-1,3-dioxane-4,6-dione O

Me

O

X

Me

O

H O

XaH Me

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BDEs of C–H Bonds

101

3-Hydrobenzo(b)furan-2-one H

H O

O

AOP

80.1

335.1

1994ZHA/BOR(e)

83.4

348.9

AOP

1994ZHA/BOR(e)

81.8

342.3

AOP

1994ZHA/BOR(e)

76.1

318.4

AOP

1993BOR/ZHA(b)

80.7

337.6

AOP

1993BOR/ZHA(b)

iso-Chroman-3-one H

H O O

3-(2-Naphthyl)-3HK4,5,6,trihydropyran-2-one H

O O

Ethyl fluorene-9-carboxylate H

CO2E t 9

8 7 6 5

1

2 4 3

Ethyl octafluoro-fluorene-9carboxylate H 8

F

CO2E t 9

F

1

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Comprehensive Handbook of Chemical Bond Energies

3.6.2

C–H BDEs with a-N, -CN, -NC, -NO, -NO2, -NN and in heterocyclic species

3.6.2.1

C–H BDEs with a-N

Table 3.6.2.1 C–H BDEs with a-N BDEs The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

(boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Methylamine

(1) 93G2.5

389.1G10.5

(1) VLPP

(1) 1975KIN/GOD

CH3NH2

(2) 96.6

404.2

(2) SPST

(2) 1981TSA

DfH0(R)Z36.3G2 (151.9G8.4)

(3) 93.9G2

392.9G8.4

(3) EI

(3) 1983BUR/CAS

(4) 88.7

371.1

(4) VLPP

(4) 1984GRE/COL

(5) 93.6

391.6

(5) Derived

(5) 2003MIR/KON

CH3ND2

(6) 92–94

385–393

(6) IR CL

(6) 1987WAT/SET

2-Azaprop-1-ene

97.5G3.5

407.9G14.6

VLPP

1993LAZ/PAP

CH3NaCH2

Ethylamine

(1) 94.0

393.3

(1) SPST

(1) 1981TSA

CH3CH2NH2

(2) 90.1G2

377.0G8.4

(2) EI

(2) 1983BUR/CAS

DfH0(R)Z26.7G2 (111.7G8.4)

(3) 97.1

406.3

(3) Re-anal.

(3) 1998BRO/BEC

(4) 93.1

389.6

(4) Correlation

(4) 2005DEN/TUM

PAC

2002LAL/ALL

PAC

2002LAL/ALL

Propylamine

(1) 91G2

380.7G8.4

C2H5CH2NH2

(2) 93.1G2

389.5G8.4

Butylamine

94G2

393.3G8.4

nC3H7CH2NH2

iso-Propylamine

(1) 95.2

398.3

(1) SPST

(1) 1981TSA

(CH3)2CHNH2

(2) 88.9G2

372.0G8.4

(2) EI

(2) 1983BUR/CAS

DfH0(R)Z16.7G2 (69.9G8.4)

(3) 94.2

394.1

(3) Re-anal.

(3) 1998BRO/BEC

(4) 90.7

379.5

(4) Correlation

(4) 2005DEN/TUM

Pentylamine

(1) 90.5G2

387.7G8.4

PAC

2002LAL/ALL

nC4H9CH2NH2

(2) 95.5G2

399.6G8.4

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BDEs of C–H Bonds

103

Dimethylamine

(1) 87G2

364.0G8.4

(1) EI

(1) 1981GIR/LOS

(CH3)2NH

(2) 94.2

394.1

(2) Derived from

(2) 1996NIST

DfH0(R)Z37.4 (156.6)

DH0 in ref. (3) 93.0

389.0

(3) Correlation

(3) 2005DEN/TUM

(1) PAC

(1) 2002LAL/ALL

Diethylamine

(1) 87G2

364.0G8.4

(CH3CH2)2NH

(1) 88.6G2

370.7G8.4

(2) 91.9

384.6

(2) Correlation

(2) 2005DEN/TUM

Dibutylamine

(1) 90.8G2

379.9G8.4

PAC

2002LAL/ALL

(n-C3H7CH2)2NH

(2) 88.9G2

372.0G8.4

Di-iso-propylamine

89.6

375.0

Correlation

2005DEN/TUM

91.9G2

384.5G8.4

PAC

2002LAL/ALL

((CH3)2CH)2NH

Dipentylamine (n-C4H9CH2)2NH

Trimethylamine

(1) 87.0G1.0

364.0G4.2

(1) VLPP

(1) 1984GRE/COL

(CH3)3N

(2) 93.2

389.8

(2) Derived from

(2) 1996NIST

DfH0(R)Z33.2G2 (138.9G8.4)

DfH0 in ref. (3) 88.9G2.4

372G10.0

(3) PAC

(4) 91G2

380.7G8.4

(4) PAC, revised

(4) 1999LAA/MUL

(5) 90.0

376.6

(5) Correlation

(5) 2005DEN/TUM

Triethylamine

(1) 85.0

355.6

(1) SPST

(1) 1981TSA

(CH3CH2)2N

(2) 91.1G2.4

381G10

(2) PAC

(2) 1997WAY/CLA

DfH0(R)Z16.4G0.5 (68.6G2.1)

(3) 90.7G0.4

379.5G1.7

(3) PAC

(3) 1999DOM/DIN

(4) 89

372.4

(4) PAC

(4) 2000KRA/CIR

(5) 91.2G2

381.6G8.4

(5) PAC

(5) 2002LAL/ALL

(1) PAC

(1) 2002LAL/ALL (2) 2005DEN/TUM

Tripropylamine

(1) 89G2

372.4G8.4

(C2H5CH2)3N

(1) 90G2

376.6G8.4

(2) 90.7

379.5

(2) Correlation

(3) 1997WAY/CLA

Tri-iso-propylamine

(1) 92.5G2

387.0G8.4

(1) PAC

(1) 2002LAL/ALL

((CH3)2CH)3N

(2) 88.4

370.0

(2) Correlation

(2) 2002DEN/DEN

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 3.6.2.1 (continued) C–H BDEs with a-N BDEs The broken bonds

(boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

Tributylamine

(1) 91.1G2.4

381G10.0

(C3H7CH2)3N

(2) 89.5G2

374.5G8.4

tert-Butyldimethylamine

90.0G2

376.6G8.4

PAC

PAC

References (1) 1997WAY/CLA (2) 2002LAL/ALL

1999DOM/DIN

tert-BuN(CH3)2

Triallylamine

(1) 82.6G0.8

345.6G3.3

(1) PAC

(1) 1999DOM/DIN

N(CH2CHaCH2)3

(2) 82.6

345.6

(2) Correlation

(2) 2002DEN/DEN

Dimethylpenylamine

91.7

383.7

Correlation

2005DEN/TUM

88.0

368.0

Correlation

2000DEN/KHU

88.6

370.8

Correlation

2005DEN/TUM

91.6

383.2

Correlation

2005DEN/TUM

91.6G1.0

383.3G4.2

PAC

1999DOM/DIN

90.7G0.4

379.5G1.7

PAC

1999DOM/DIN

85.4G2.1

357.3G8.8

PAC

1999DOM/DIN

PhN(CH3)2

Phynelmethylamine PhCH2NH2

Dimethylbenzylamine PhCH2N(CH3)2

Dimethylbenzylamine PhN(CH3)(CH2CH3)

Phenyldiethylamine PhN(CH2CH3)2

Diphenylmethylamine Ph2NCH3

Phenyldibenzylamine PhN(CH2Ph)2

7366—CHAPTER 3—6/2/2007—13:26—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

Tribenzylamine

105

89.1G0.6

372.8G2.5

PAC

1999DOM/DIN

81.1G0.7

339.3G2.9

PAC

1999DOM/DIN

89.5

374.3

Derived

2003MIR/KON

N(CH2Ph)3

Phenyldiallylamine PhN(CH2CHaCH2)2

Ethane-1,2-diamine H2NCH2CH2NH2

N,N-Dimethylaniline, substituted H

CH2 Y

N(CH3)

YaH

(1) 91.7G1.3

383.7G5.4

(1) PAC

(1) 1999DOM/DIN

DfH0(R, for YaH)Z63.6G3

(2) 85.7

358.4

(2) Correlation

(2) 2000DEN/KHU

4-Cl

(1) 89.8G1.4

375.7G5.9

4-Me

(1) 89.9G2.5

376.1G10.5

4-CF3

(1) 92.2G1.7

385.8G7.1

(266.1G12.6)

2-tBu

(1) 94.7G1.3

396.2G5.4

2,2-Me2

(1) 90.2G1.5

377.4G6.5

90.5

378.7

AOP

1993ZHA/BOR

84.9

355.2

AOP

1997LIU/HUA

90.8

380

AOP

1997CHE/LIU

Benzyl trimethylammonium chloride K PhCHC 2 NMe3Cl

Fluorenyl trimethylammonium bromide FLHCNMe3BrK

Benzyl trimethylammonium bromide K PhCHC 2 NMe3Br

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Comprehensive Handbook of Chemical Bond Energies

3.6.2.2

C–H BDEs with a-CN and -NC

Table 3.6.2.2 C–H BDEs with a-CN and -NC BDEs The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

(boldfaceZrecommended data; reference in parentheses)

Methods (reference in

kcal/mol

kJ/mol

parentheses)

Methanenitrile

(1) 126.1G0.4

527.6G1.7

(1) Recommended

(1) 1994BER/ELL

H–CN DfH0(R)Z105.5G1.1

(2) 126.3G0.2 (3) 125.0G0.1,

528.5G0.8 523.0G0.4

(2) Photolysis (3) TIPPS

(2) 2000COO/LAN (3) 2006HU/ZHA

105.1

439.8

Correlation

2004TUM/DEN

112.6

471.3

Correlation

2004TUM/DEN

(441.4G4.6)

Prop-2-enenitrile

References

at 0 K

CH2CHCN

Prop-2-ynenitrile CHbCCbCN

Acetonitrile

(1) 93G2.5

389.1G10.5

(1) Review

(1) 1982MCM/GOL

CH3CN

(2) 94.8G2.1

396.6G8.8

(2) PES

(2) 1987MOR/ELL(b)

(3) 96

401.7

(3) PAC

(3) 1995WAY/LUS

(4) 97.0G1

405.8G4.2

(4) Neg. ion cycle

(4) 2000LAF/SZA

(5) 94.8G2.1

396.6G8.8

(5) GPA

(5) 2003REE/HAR

(1) 89.8G2.3 (2) 94.0G3

375.7G9.6 393.3G12.6

(1) VLPP (2) Derived from

(1) 1975KIN/GOD (2) 1986PED/NAY

DfH0(R)Z60.4G1 (252.6G4.2)

Propanenitrile CH3CH2CN DfH0(R)Z54.2G3 (226.7G12.6)

DfH0 in ref. (3) 90G2

376.6G8.4

(3) AP

(3) 1993HOL/LOS

(4) 94.9

397.1

(4) Re-anal.

(4) 1998BRO/BEC

(5) 92.5

387.2

(5) Correlation

(5) 2004TUM/DEN

2-Methylpropanenitrile

(1) 86.5G2

361.9G8.4

(1) VLPP

(1) 1976KIN/GOD

(CH3)2CHCN DfH0(R)Z45.5G3

(2) 91.9 (3) 89.0

384.5 372.2

(2) Re-anal. (3) Correlation

(2) 1998BRO/BEC (3) 2004TUM/DEN

96.3

402.9

Correlation

2004TUM/DEN

(190.4G12.6)

2,2-Dimethylpropanenitrile (CH3)3CCN

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BDEs of C–H Bonds

Phenylacetonitrile

107

82.3

344.3

AOP

1993BOR/ZHA(b)

80

334.7

AOP

1992BOR/ZHA

Diphenylacetonitrile

(1) 77.5

324.3

AOP

(1) 1988BOR/CHE(b)

Ph2CHCN

(2) 76.8

321.3

2-Methyl-2-

97.7

408.7

Correlation

2004TUM/DEN

83.8

350.6

AOP

1993BOR/ZHA(b)

81.7

341.8

AOP

1993BOR/ZHA(b)

81

338.9

AOP

1992BOR/ZHA

76

318.0

AOP

1992BOR/ZHA

Methae-1,1-dicarbonitrile

(1) 90

376.6

(1) AOP

(1) 1991BOR/CHE

CH2(CN)2

(2) 87.6

366.5

(2) Re-anal.

(2) 1998BRO/BEC

1,1,2,2-Tetramethylethane-1,2-

96.7

404.4

Correlation

2004TUM/DEN

PhCH2CN

2-Phenyl-propanenitrile PhC(Me)CHCN

(2) 1993BOR/ZHA(b)

phenylpropanenitrile C6H5C(CH3)2CN

Pentafluorophenyl acetonitrile C6F5CH2CN

Di(pentafluorophenyl)acetonitrile (C6F5)2CHCN

2-cyclo-Hexyl-2-phenylethanenitrile cyclo-C6H11CH(Ph)CN

2-Phenyl-2-(2-pyridyl)ethanenitrile cyclo-PyNCH(Ph)CN

carbonitrile (CH3)2(CN)CC(CN)(CH3)2

(continued)

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108

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.2.2 (continued) C–H BDEs with a-CN and -NC

The broken bonds

BDEs (boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) 2-Aminoethanenitrile

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

84.9

355.2

Re-anal.

1998BRO/BEC

84.6

354.0

Re-anal.

1998BRO/BEC

77

322.2

AOP

1992BOR/ZHA

95.3

398.7

AOP

1990BOR/ZHA

87.6

366.5

AOP

1990BOR/ZHA

iso-Cyanomethane CH3NC

(1) 91.0G2.1 (2) 93G3

380.7G8.8 389.1G12.6

(1) PES (2) PES

(1) 1987MOR/ELL(b) (2) 2002NIM/DAV

DfH0(R)Z80G4

(3) 96.7

404.7

(3) Derived

(3) 2004JAN/ROS

CH2(CN)(NH2)

Methylmethane-1,1dicarbonitrile MeCH(CN)2

Phenylmethane-1,1dicarbonitrile CNCH(Ph)CN

1-Acetonitrile trimethylammonium chloride K MeC 3 NCH2CNCl

1-Acetonitrile pyridinium chloride PyNCCH2CNClK

(334.7G16.7)

7366—CHAPTER 3—6/2/2007—13:27—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

3.6.2.3

109

C–H BDEs with a-NO, -NO2 and -NN

Table 3.6.2.3 C–H BDEs with a-NO, -NO2 and -NN BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Nitromethane

(1) 97.4

407.5

(1) AOP

(1) 1994BOR/SAT

CH3NO2 DfH0(R)Z27.5G3 (115.1G12.6)

(2) 96.3 (3) 99.3

402.9 415.4

(2) Derived (3) Correlation

(2) 2000MIR/VOR (3) 2004TUM/DEN

Nitroethane

(1) 91.4

382.4

(1) AOP

(1) 1994BOR/SAT

CH3CH2NO2

(2) 98.1

410.5

(2) Derived

(2) 2000MIR/VOR(b)

DfH0(R)Z14.8G3 (61.9G12.6)

(3) 96.2

402.4

(3) Correlation

(3) 2004TUM/DEN

Nitropropane

98.1

410.5

Derived

2000MIR/VOR(b)

97.3

407.1

Derived

2000MIR/VOR(b)

99.7

417.1

Correlation

2004TUM/DEN

Nitropentane C4H9CH2NO2

96.2

402.5

Derived

2000MIR/VOR(b)

2-Nitropropane

(1) 86.8

363.2

(1) AOP

(1) 1994BOR/SAT

(CH3)2CHNO2

(2) 94.7

396.2

(2) Derived

(2) 2000MIR/VOR(b)

DfH0(R)Z1.5G3 (6.3G12.6)

(3) 94.4

394.9

(3) Correlation

(3) 2004TUM/DEN

1,1-Dinitroethane

98.2

410.9

Derived

2000MIR/VOR(b)

97.8

409.2

Derived

2000MIR/VOR(b)

C2H5CH2NO2

Nitrobutane C3H7CH2NO2

2-Methyl-2-nitropropane (CH3)3CNO2

(CH3)CH(NO2)2

1,1-Dinitropropane (C2H5)CH(NO2)2

(continued)

7366—CHAPTER 3—6/2/2007—13:28—JEBA—15359—XML MODEL B – pp. 19–145

110

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.2.3 (continued) C–H BDEs with a-NO, -NO2 and -NN

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) 1,1-Dinitrobutane

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

98.3

411.3

Derived

2000MIR/VOR(b)

96.9

405.4

Derived

2000MIR/VOR(b)

88.4

369.9

AOP

1994BOR/SAT

86.8

363.2

AOP

1994BOR/SAT

Nitro-cyclo-hexane cyclo-C6H11NO2

88.6

370.7

AOP

1994BOR/SAT

Methylnitroamine CH3NHNO2

82.2

344.0

Derived

2003MIR/KON

Nitro[(nitroamino)methyl]amine

81.6

341.6

Derived

2003MIR/KON

81.6

341.6

Derived

2003MIR/KON

78.4

328.2

Derived

2003MIR/KON

(C3H7)CH(NO2)2

1,1-Dinitropentane (C4H9)CH(NO2)2

Nitro-cyclo-propane cyclo-C3H5NO2

Nitro-cyclo-pentane cyclo-C5H9NO2

CH2(NHNO2)2

Nitro[2-(nitroamino)ethyl]amine (CH2)2(NHNO2)2

Nitro[5-(nitroamino)pentyl]amine (CH2)6(NHNO2)2

7366—CHAPTER 3—6/2/2007—13:28—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

111

1-Phenylnitroethanes, substituted NO2 Y

C

H

CH3

YaH

85.4

357.3

4-F

86.1

360.2

4-Me

85.6

358.2

3-MeO

86.9

363.6

AOP

1995BOR/ZHA(c)

DfH0(R)Z40.4G3 (169.0G12.6)

4-MeO

84.9

355.2

3-NO2

86.1

360.2

4-NO2

86.9

363.6

3,5-(NO2)2

88.7

371.1

86.1

360.2

AOP

1994BOR/SAT

89.7

375.5

Derived

2000MIR/VOR

86.3

361.0

Derived

2000MIR/VOR

82.9

346.9

AOP

1992ZHA/BOR

72.3

302.5

Derived

2001MIR/KOS

77.6

324.7

72.3

302.5

97G2

405.8G8.4

PES

1998CLI/WEN(b)

Nitro(phenylmethoxy) methane PhCH2OCH2NO2

Dinitromethane CH2(NO2)2

Trinitromethane CH(NO2)3

1-Aza-1-methyoxy-3-phenyl-2benzylpro-1-ene (PhCH2)2CaNOMe

Nitrozoamines (NO2)3CCH2N(NO2)CH2CH2– CH2N(NO2)CH2C(NO2)3 (NO2)2CHCH2N(NO2)CH2CH2– CH2N(NO2)CH2CH(NO2)2 (NO2)3CCH2N(NO)CH2CH2– CH2N(NO)CH2C(NO2)3

Diazomethyl radical H–HCNN

(continued)

7366—CHAPTER 3—6/2/2007—13:28—JEBA—15359—XML MODEL B – pp. 19–145

112

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.2.3 (continued) C–H BDEs with a-NO, -NO2 and -NN BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) Diazocarbene

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

79.1G4

331G17

PES

1998CLI/WEN(b)

Methylhydrazine H2NNH(CH3)

98

410

Pyrolysis

1964EBE

1,1-Dimethylhydrazine

98

410

Pyrolysis

1964EBE

H–CNN

HNN(CH3)2

3.6.2.4

C–H BDEs in heterocyclic species

Table 3.6.2.4 C–H BDEs in Heterocyclic Species BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

recommended data; reference in parentheses) kcal/mol

kJ/mol

H

(1) 90.1G2.4

377G10.0

H

(2) 87

364.0

Methods (reference in parentheses)

References

Pyrrolidine H N

PAC

(1) 1997WAY/CLA (2) 2000KRA/CIR

DfH0(R)Z34.1G3 (142.7G12.6)

Pyrrole NH

2 3

(1) 118.4G1

495.4G4.2

(1) Shock tube

(1) 1991MAC/COL

(2) 112.3G1

469.9G4.2

(2) PI

(2) 1994BLA/NOR

119G4

497.9G17

Derived

2005GIA/ICH

C–H bond at 2 and 3 site DfH0(Pyrrol-2-yl)Z92.2 (385.8) DfH0(Pyrrol-3-yl)Z92.2 (385.8)

Imidazole NH

H H

N

H

7366—CHAPTER 3—6/2/2007—13:29—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

Pyrazole H

H 5 1N 2

H

N

H

113

121G4

506G17

Derived

2006GIA/ICH

Correlation

2005DEN/TUM

Cyclo-hexalamines, substituted NX1X2 H

X1aH

94.6

395.9

H

X2aH Me

92.7

388.0

Me

Me

91.1

381.0

(1) 89.5

374.5

(1) PAC

(1) 1993CLA/WAY

(2) 92.0G2.4

385G10.0

(2) PAC

(2) 1997WAY/CLA

(3) 92.2

385.6

(3) Correlation

(3) 2005DEN/TUM

92.6

387.3

Correlation

2005DEN/TUM

96.2G2

402.5G8.4

PAC

2002LAL/ALL

Piperidine NH

H H

0

DfH (R)Z28.6 (119.7)

Di-cyclo-hexylamine NH H H

Quinuclidine

N

H H

1,4-Diazabicyclo(2.2.2)octane N N

H H

(1) 93

389.1

(1) Electrochemical

(1) 2000ZHE/EVE

(2) 93.8G2

392.5G8.4

(2) PAC

(2) 2002LAL/ALL

(1) 102.7 (2) 105G0.2

429.7 439.3G0.8

Shock tube

(1) 1992DOU/MAC (2) 1997KIE/ZHA

Pyridine 4 3 12

N

C–H bond at 2 site

(continued)

7366—CHAPTER 3—6/2/2007—13:29—JEBA—15359—XML MODEL B – pp. 19–145

114

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.2.4 (continued) C–H BDEs in Heterocyclic Species BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

reference in parentheses) kcal/mol

kJ/mol

at 3 site

(2) 112G2

468.6G8.4

at 4 site

(2) 112G2

468.6G8.4

Methods (reference in parentheses)

References

DfH0(pyrid-2-yl)Z86.5 (361.9) DfH0(pyrid-3-yl)Z93.5 (391.2) DfH0(pyrid-4-yl)Z93.5 (391.2)

Pyrimidine 5

4 N 3 12

N

C–H bond at 2 site

(1) 95.8

400.8

(2) 98G2

410.0G8.4

Shock tube

(1) 1992DOU/MAC

at 4 site

(1) 102.8 (2) 103G2

430.1 431.0G8.4

at 5 site

(1) 111.2

465.3

(2) 112G2

468.6G8.4

103G2

431G8

Shock tube

1997KIE/ZHA

2-CH3

87.2

365.0

Correlation

2002KRO/TUM

3-CH3

90.4

378.2

4-CH3

86.5

362.1

2,4,6-(CH3)3

87.7

366.9

(2) 1997KIE/ZHA

DfH0(Pyrimid-2-yl)Z92.7G3 (387.9G12.6) DfH0(Pyrimid-4-yl)Z97.7G3 (408.4G12.6) DfH0(Pyrimid-5-yl)Z106.7G3 (446.4G12.6)

Pyrazine H

N

H

N

2 3

H H

DfH0(pyrazin-2-yl)Z97.8G3 (409.2G12.6)

Pyridines, substituted 543 61 2

N

CH2

H

7366—CHAPTER 3—6/2/2007—13:29—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

115

1,4-Dihydropyridines, substituted X1

X4

H N H

X X3

X2

X1aC(O)NH2, X2aX3aX4aH XaPh

69.2

289.5

AOP

2003ZHU/LI

PhCH2

67.9

284.1

4-Cl–C6H4

69.1

289.1

4-Br–C6H4

69.2

285.5

4-CH3–C6H4

69.2

285.5

4-CF3–C6H4

69.5

290.8

4-MeO–C6H4

69.4

290.4

69.4

290.4

68.8

287.9

(1) 90

376.6

(1) PAC

(1) 1993CLA/WAY

(2) 93

389.1

(2) PAC, revised

(2) 1999LAA/MUL

2-CH3

87.6

366.6

Correlation

2002KRO/TUM

3-CH3

88.9

372.1

4-CH3

86.1

360.1

5-CH3

87.5

366.3

6-CH3 7-CH3

88.7 88.7

371.0 371.0

8-CH3

90.3

377.8

X1aX2aC(O)NH2, X3aX4aMe XaH Me

Piperazine H N

4 3 1 2

N H

H

H

Quinlines, substituted 8 7 6 5

N

12 3

4

CH2

H

2-Benzyl pyridine H N

1

CH

(1) 82.3

344.3

(1) VLPP

(1) 1984ROS/MCM

(2) 82

343.1

(2) AOP

(2) 1992ZHA/BOR

4

(continued)

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116

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.2.4 (continued) C–H BDEs in Heterocyclic Species BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

3-Benzyl pyridine N

6 1 2 5 4 3

H

84

351.5

AOP

1992ZHA/BOR

CH

4-Benzyl pyridine N

6 1 2 5 3 4

H

(1) 82.3

344.3

(1) VLPP

(1) 1984ROS/MCM

(2) 83

347.3

(2) AOP

(2) 1992ZHA/BOR

N

66

276.1

AOP

1992ZHA/BOR(b)

N

68

284.5

N

72

301.2

N

71.5

299.2

N

72

301.2

N

71

297.1

73

305.4

CH

Fluorenes, substituted R

R=

H

2

N

7366—CHAPTER 3—6/2/2007—13:30—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

117

Fluorenes, substituted R2

R1

N

H

R1ZMe R2ZMe

71.5

299.2

Et

Et

70.5

295.0

i-Pr

i-Pr

73

305.4

n-Bu

Me

72

301.2

PhCH2

Me

72.5

303.3

AOP

1992ZHA/BOR(b)

Electrochemical

(1) 1998ANN/FRA

10-Methyl-9,10-dihydro-acridine, substituted X

H

N CH3

XaH CN

(1) 72.0G1.6

301.2G6.7

(2) 73.7

308.4

(1) 71.3G1.5

298.3G6.3

84.7

354.4

AOP

1993ZHA/BOR

84.7

354.4

AOP

1993ZHA/BOR

(2) 2003ZHU/LI

3-Methyl-1-benzylpyridinium bromide Me PhCH2 N

Br-

1-Benzyl pyridinium chloride K PhCHC 2 NPyCl

7366—CHAPTER 3—6/2/2007—13:30—JEBA—15359—XML MODEL B – pp. 19–145

118

3.6.3

Comprehensive Handbook of Chemical Bond Energies

C–H BDEs with a-O, -N and their groups

Table 3.6.3 C–H BDEs with a-O, -N and Their Groups BDEs The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) (1Z)-2-Aza-2-methoxy-1,1-

(boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

94.9

397.1

AOP

1992BOR/JI

90.7G2

379.5G8.4

PAC

2002LAL/ALL

Methyldiethanolamine ((HOCH2CH2)2(CH3))N

87.1G2

364.4G8.4

PAC

2002LAL/ALL

Triethanolamine

90.8G2

379.9G8.4

PAC

2002LAL/ALL

PAC

2002LAL/ALL

phenylvinylamine PhC(NH2)aNOCH3

Ethanolamine HOCH2CH2NH2

(HOCH2CH2)3N

Tri-iso-propanolamine

(1) 90.8G2

379.9G8.4

((HOCH2)CH(CH3))3N

(2) 93.2G2

389.9G8.4

2-Hydroxypropanenitrile

87.3

365.3

Re-anal.

1998BRO/BEC

90.3

377.8

Re-anal.

1998BRO/BEC

77.5

324.3

AOP

1992BOR/ZHA

79.5

332.6

AOP

1992BOR/ZHA

(CN)CHMe(OH)

2-Methoxyethanenitrile (CN)CH2OMe

2-Methoxy-2-phenylethanenitrile MeOCH(Ph)CN

2-Phenyl-2-phenoxyethanenitrile PhOCH(Ph)CN

7366—CHAPTER 3—6/2/2007—13:30—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

N,N-Dimethylacetamide

119

91.0

380.9

Correlation

2000DEN/KHU

77

322.2

PAC

1993CLA/WAY

93.1

389.5

Correlation

2000DEN/KHU

81.7G0.5

341.8G2.1

Derived

1999FOR/BUT

w105

w439

Derived

1999FOR/BUT

85.7

358.6

AOP

2002ALN/ZHA

78.3

327.6

Re-anal.

1998BRO/BEC

96.8

405.0

AOP

1997CHE/LIU

%82.0

%343

Electrochemical

1997ZHA/LIN

%78.6

%329

Electrochemical

1997ZHA/LIN

Me2NC(O)CH3

Methyl 2-(dimethylamino)acetate Me2NCH2C(O)Me

N-iso-Propylacetamide (CH3)2CHNHC(O)Me

N,N-Dimethylformamide H–C(O)N(CH3)2

N,N-Dimethylformamide HC(O)N(CH3)2

Phenyl pyridyl ketone PhC(O)CH2Py

2-(Dimethylamino)-1-phenylethan-1-one N(CH3)2CH2C(O)Ph

Phenyl methylene ketone trimethylammonium bromide K PhCðOÞCHC 2 NMe3 Br

Glycine ion NH2CH2C(O)OK

Glycine NH2CH2C(O)OH

(continued)

7366—CHAPTER 3—6/2/2007—13:31—JEBA—15359—XML MODEL B – pp. 19–145

120

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.3 (continued) C–H BDEs with a-O, -N and Their Groups

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) 2-Cyanoacetic acid

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

95.2

398.4

Correlation

2002TUM/KRO

2-(Acetylamino)acetic acid CH3C(O)NHCH2C(O)OH

96.1

402.2

Correlation

2002TUM/KRO

2-(Acetylamino)propanioc acid

93.9

393.0

Correlation

2002TUM/KRO

84.3

352.7

Re-anal.

1998BRO/BEC

79-83

331-347

PAC

1993CLA/WAY

88.0

368.0

Correlation

2000DEN/KHU

Ethylamino acetate CH3C(O)ONHCH2CH3

95.4

399.2

Correlation

2005DEN/TUM

(Methylethyl)amino acetate

94.5

395.5

Correlation

2005DEN/TUM

92.5

386.9

Correlation

2005DEN/TUM

81.3G3.6

340G15

PAC

1998JON/WAY

(CN)CH2C(O)OH

CH3C(O)NHCH(CH3)C(O)OH

Methyl-2-aminoacetate NH2CH2C(O)OMe

Ethyl-2-aminoacetate NH2CH2C(O)OEt

Ethyl-3-(dimethylamino) prooanoate Me2N(CH2)2C(O)OEt

CH3C(O)ONHCH(CH3)2

Dimethylamino acetate CH3C(O)ON(CH3)2

Glycine anhydride NH2CH2C(O)OCH2NH2

7366—CHAPTER 3—6/2/2007—13:31—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

tert-Butyl-2-aminopropanoate

121

81.3

340.2

Re-anal.

1998BRO/BEC

Methyl 3-cyanopropanoate CH2(CN)CH2C(O)OCH3

91.7

383.8

Correlation

2004TUM/DEN

Alanine anhydride

77.7G3.6

325G15

PAC

1998JON/WAY

(1) 80.9

338.5

AOP

(1) 1993BOR/ZHA(b)

(2) 80.3

336.0

F

(2) 80.3

336.0

Cl

(2) 80.8

338.1

Me

(2) 80.0

334.7

MeO

(2) 78.3

327.6

NH2CHMeC(O)OtBu

Me(NH2)CHC(O)OCHNH2Me

Ethyl-2-cyano-2-phenylacetates, substituted H Y

C

C(O)OEt

CN

YaH

(2) 2000CHE/LIU

MeCO2

(2) 82.0

343.1

CF3

(2) 82.2

343.9

CN

(2) 83.2

348.1

85.2

356.5

AOP

1993BOR/ZHA(b)

78

326.4

PAC

1993CLA/WAY

Ethyl-2-cyano-2-pentafluorophenyl-acetate C6F5CH(CN)C(O)OEt

4,4-Dimethyl pyrrolidin-3-one H O Me

H N

Me

Me

(continued)

7366—CHAPTER 3—6/2/2007—13:31—JEBA—15359—XML MODEL B – pp. 19–145

122

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.3 (continued) C–H BDEs with a-O, -N and Their Groups

The broken bonds

BDEs (boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1,3-Oxazolidines, substituted H

H

O

N

R

RaC2H5

88.7

371.2

C6H5

88.4

369.9

cyclo-C6H11

88.5

370.1

Raiso-C3H7

87.2

364.8

C6H5

86.7

362.6

Correlation

2005TUM

Correlation

2005TUM

PAC

1993CLA/WAY

1,3-Oxazolidines, substituted C6H5

H

O

N

C6H5

3-Ethyl-4,4-dimethyl-1,3-oxazolidine H

X

O

Et

N

CH3 CH3

XaMe C(O)OMe

82.1

343.5

84.1

351.9

Morpholines, substituted X

N O

XaH

H H

(1) 90.8

379.9

(1) PAC

(1) 1993CLA/WAY

(2) 93.0G2.4

389G10.0

(2) PAC

(2) 1997WAY/CLA

(3) 94

393.3

(3) PAC

(3) 1999LAA/MUL

(4) 92G2

384.9G8.4

(4) PAC

(4) 2002LAL/ALL

7366—CHAPTER 3—6/2/2007—13:32—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

123

Ph

(5) 86.3

361.0

C(O)Ph

(5) 95.8

401.0

(5) Correlation

(5) 2005DEN/TUM

89.3G4

373.6G16.7

PAC

2002LAL/ALL

79.3

331.8

Electrochemical

2003ZHU/YAN

36.3

151.9

Electrochemical

2003ZHU/YAN

(1) 75

313.8

(1) PAC

(1) 1993CLA/WAY

(2) 78

326.4

(2) PAC, revised

(2) 1999LAA/MUL

75.3

315.1

PAC

1993CLA/WAY

77.5

324.3

7a-ethyl-1H,3H,5H,7H-1,3oxazolidino-(3,4-C)1,3oxazolidine

O

O

N

H

H

NADH H R

N H CONH 2

RZadenosine diphosphoribosyl

NADHC% H R

N H CONH2

RZadenosine diphosphoribosyl

2-Oxomorpholine 3 2

H H

1 O

N

4,5,5-Trimethyl morpholin-2-one O

H

O N CH3 CH3

XaH CH3

X CH3

(continued)

7366—CHAPTER 3—6/2/2007—13:32—JEBA—15359—XML MODEL B – pp. 19–145

124

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.3 (continued) C–H BDEs with a-O, -N and Their Groups BDEs (boldfaceZrecommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Phenyl piperazin-2-yl ketones, substituted R N C N

COPh H

R

RaMe Et

73

305.4

72

301.2

AOP

1992ZHA/BOR(b)

Electron attach.

2004DEN/PTA

Uracil H

O

3

2 N 4

N

H

1

O

5

6

H

H

C–H bonds at site 5

119.9

501.7

6

115.3

482.4

1,4-Diazaperhydroine-2,5-diones, substituted O

X

Bu

N

H N

Bu

Me O

XaH Me

92.4 89.4

386.6 374.0

Re-anal.

1998BRO/BEC

94.4

395.0

Correlation

2000DEN/KHU

83.3

348.6

Correlation

2000DEN/KHU

Phenyl piperidyl ketone O

N H

H

Ph

Morpholin-4-yl phenyl ketone O O

N H

H Ph

7366—CHAPTER 3—6/2/2007—13:32—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

125

1,3,5-Trihydropyrimidine-2,4,6trione O NH

H H

95.1

O

NH

397.8

Correlation

2005DEN/TUM

AOP

1992ZHA/BOR(b)

AOP

1992ZHA/BOR(b)

O

1-Phenyl 2,2-dipiperidylethan-1-one, analogues H X

N 2

C

COPh

XaCH2

74

309.6

O

75

313.8

69

288.7

Fluorenes, substituted R MeO

RZ

3.6.4

H OMe

N

C–H BDEs with a-C(S), -S, -SO, -SO2

Table 3.6.4 C–H BDEs with a-C(S), -S, -SO, -SO2 BDEs The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) Thioformaldehyde

(boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

95.5G1.2

399.6G5.0

Recommended

(1) 92.4G2.0 (2) 93.9G2.0

386.6G8.4 392.9G8.4

(1) PIMS (2) Recommended

References 1994BER/ELL

H–C(S)H DfH0(R)Z71.8G2 (300.4G8.4)

Methanethiol CH3SH

(1) 1992RUS/BER (2) 1994BER/ELL

DfH0(R)Z36.3G2 (151.9G8.4)

(continued)

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126

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.4 (continued) C–H BDEs with a-C(S), -S, -SO, -SO2 BDEs The broken bonds

(boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Dimethyl sulphide

(1) 91G2.5, 0 K

380.7G10.5

(1) PD

CH3SCH3

(2) 93.7G1.4

392.0G5.9

(2) RF detec.

(1) 1991NOU/NOR (2) 1994JEF/NIC

DfH0(R)Z32.7G1.4 (136.8G5.9)

(3) 91.8G0.6,

384.1G2.5

(3) PI

(3) 2001CHE/CHE

Correlation

(1) 2005DEN/TUM

0K

Diethyl disulfide

(1) 93.3

390.2

CH3CH2SCH2CH2CH3

(2) 92.2

385.7

1,1-Diethylthio-ethane

89.9

376.1

Correlation

Correlation

(2) 2005TUM

2005DEN/TUM

(CH3CH2S)2CHCH3

1,1-Diethylthio-3-methylbutane

(1) 93.0

389.0

(CH3CH2S)2CHCH(CH3)2

(2) 90.0

376.5

(1) 2003TUM/DEN

1,1-Dibutylthio-3-methylbutane

92.1

385.6

Correlation

2003TUM/DEN

95.8G3

400.8G12.6

CID

1998REN/WOR

87.8

367.3

Correlation

2005TUM

iso-C3H7

88.2

369.1

n-C6H13

87.8

367.5

(2) 2005TUM

(CH3CH2CH2CH2S)2CHCH(CH3)2

Adduct of BH3 and S(CH3)2 H3BS(CH3)2

2-Alkyl-1,3-dithiolanes S S

H R

RaCH3

7366—CHAPTER 3—6/2/2007—13:33—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

127

2,2-Methyl-1,3-dithiolanes S

CH 3

S

CH3

96.6

404.0

Correlation

2005TUM

89.5

374.6

Correlation

2005DEN/TUM

C5H11

89.4

374.1

C8H17

90.3

378.0

89.4

374.2

Correlation

2005TUM

H H

2-Alkyl-thio-2HK3,4,5,6-tetrahydropyrans H O

R

S

RaC2H5

1,3-Oxathianes, substituted R2

O

H

S

R1

R1aC3H7, R2aCH3 i-C3H7,

CH3

89.6

374.7

C3H7,

C5H11

89.5

374.6

92.7

388.0

Correlation

2005TUM

88.8

371.5

Correlation

2005TUM

89.4

373.9

(1) 91.0

380.9

Correlation

2005TUM

n-C3H7

(2) 89.2

373.1

iso-C3H7

(1) 87.2

365.0

1,3-Dithianes, substituted S S

H iso-Pr

2,4-Dialkel-1,3-dithianes S C4H9

S

H R

Ran-C3H7 iso-C3H7

4-Alklyl-1,3-dithianes S

H S

RaCH3

R

(continued)

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128

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.4 (continued) C–H BDEs with a-C(S), -S, -SO, -SO2 BDEs The broken bonds

(boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

2-Alkyl-1,3-dithiepanes S

H R

S

RaCH3

88.3

369.4

n-C3H7

88.4

369.8

Correlation

2005TUM

iso-C3H7

88.5

370.1

92.7

388.0

Correlation

2003TUM/DEN

91.9

384.7

Correlation

2003TUM/DEN

92.9

388.8

Correlation

2005TUM

93.0

389.1

AOP

1993ZHA/BOR

AOP

4-(Methylethyl)-1,3-dithiepane S

CH(CH3)2 S

H

4-(Methylethyl)-1,3-dithiocane S

CH(CH3)2 S

H

1,3,5-Trithiane S

S S

H H

Phenyl methyl sulphide PhSCH3 DfH0(R)Z64.2G3 (268.6G12.6)

Benzyl phenyl sulphide

(1) 84.2

352.3

PhCH2SPh

(2) 82.2

343.9

(1) 1993ZHA/BOR

81.5

341.0

AOP

1992BOR/ZHA

82.4

344.8

AOP

1992BOR/ZHA

(2) 1998BOR/LIU

DfH0(R)Z104.1G3 (435.6G12.6)

Di(phenylthio)phenyl methane (PhS)2CHPh

Phenyl diphenylmethyl sulphide PhSCHPh2

7366—CHAPTER 3—6/2/2007—13:33—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

129

1,3-Oxathiolanes, substituted H

O

R

S

RaH

(1) 91.0

380.9

(2) 90.4

378.3

Correlation

(1) 2002TUM/KRO

Me

(1) 90.3

377.8

Et

(1) 90.3

377.8

(2) 88.6

370.8

Pr

(2) 88.7

371.1

iso-Pr

(1) 90.3

377.8

(2) 88.6

370.6

94.3

394.7

Correlation

2005DEN/TUM

94

393.3

AOP

1998BOR/LIU

99

414.2

AOP

1991BOR/HAR

103

431.0

AOP

1991BOR/HAR

99

414.2

AOP

1991BOR/HAR

95

397.5

AOP

1995ZHA/BOR

91

380.7

AOP

1992ZHA/BOR

(2) 2005TUM

2,2-Dimeyl-oxathiolane Me

O H

S

Me

H

Dimethyl sulphoxide CH3SOCH3 DfH0(R)Z5.7G3 (23.8G12.6)

Dimethyl sulphone CH3SO2CH3 DfH0(R)ZK42.3G3 (K177.0G12.6)

Methyl trofluoromethyl sulphone CH3SO2CF3

Methyl phenyl sulphone CH3SO2Ph DfH0(R)ZK13.7G3 (K57.3G12.6)

Methyl p-NO2-phenyl sulphone CH3SO2(p-NO2-C6H4)

Benzyl methyl sulphone PhCH2SO2Me DfH0(R)ZK26.1G3 (K109.2G12.6)

(continued)

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130

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.4 (continued) C–H BDEs with a-C(S), -S, -SO, -SO2 BDEs The broken bonds

(boldfaceZrecommended data; reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) Benzyl trifluoromethyl sulphone

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

89

372.4

AOP

1992ZHA/BOR

90

376.6

AOP

1992ZHA/BOR

AOP

(1) 1998BOR/LIU

PhCH2SO2CF3

Benzyl tert-butyl sulphone PhCH2SO2-tert-Bu

Benzyl phenyl sulphone PhCH2SO2Ph

(1) 89.7

375.3

DfH0(R)Z1.7G3 (7.1G12.6)

(2) 90.2

377.4

Di(methyl sulphonyl) methane

101.4

424.3

AOP

1994BOR/ZHA

113

472.8

AOP

1991BOR/HAR

101.3

423.8

AOP

1994BOR/ZHA

100.1

418.8

AOP

1994BOR/ZHA

99.7

417.1

AOP

1994BOR/ZHA

98

410.0

AOP

1994BOR/ZHA

87.3

365.3

AOP

1991BOR/ZHA

(2) 1992ZHA/BOR

CH2(CH3SO2)2

Di(trifluoromethyl sulphonyl) methane CH2(CF3SO2)2

Di(ethyl sulphonyl) methane CH2(EtSO2)2

Di(isopropyl sulphonyl) methane CH2(iso-PrSO2)2

Di(t-butyl sulphonyl) methane CH2(tert-BuSO2)2

Di(phenyl sulphonyl) methane CH2(PhSO2)2

((Diphenylmethyl)sulfonyl)-benzene Ph2CHSO2Ph DfH0(R)Z24.4G3 (K102.1G12.6)

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BDEs of C–H Bonds

Di(phenylthio) methane

131

89

372.4

AOP

1995ALN/ZHA

99.4

415.9

AOP

1995ZHA/ZHA

97.4

407.5

AOP

1995ZHA/ZHA

96.5

403.8

AOP

1995ZHA/ZHA

PhS(O)(aNSO2C7H7)CH3

103.1

431.4

AOP

1995ZHA/ZHA

PhSO2CH(CHaCH2)(SiMe3)

99.8

417.6

2,2-Dimethyl-1-(phenylsulfonyl)-

91.1

381.2

AOP

1995ZHA/ZHA

83.2

348

AOP

1997CHE/LIU

Benzyl dibutylsulfonium bromide

(1) 84.1

352

AOP

K PhCHC 2 SðnBuÞ2 Br

(2) 83.8

350.6

Phenyl methylene ketone

94.9

397

AOP

(1) 83.1

347.7

AOP

(2) 82.5

345.2

CH2(SPh)2

2,2,2-Trimethyl-1-(phenylfonyl)-2silaethane PhSO2CH2SiMe3

2,2,2-Triphenyl-1-(phenylfonyl)-2silaethane PhSO2CH2SiPh3

1-(1,1-Dimethyl)-1-silaethyl)-2,2dimethyl-1-(phenylsulfonyl)-2silapropane, PhSO2CH(SiMe3)2

Methyl N-(p-tolylsulfonyl)phenyloxosulfoximes

2-sila-vinylpropane PhS(O)(aNSO2C7H7)CH3

Benzyl dimethylsulfonium bromide K PhCHC 2 SMe2 Br

(1) 1997CHE/LIU (2) 1998CHE/LIU

1997CHE/LIU

dibutylsulfonium bromide K PhCðOÞCHC 2 SðBuÞ2 Br

Benzyl dibutylsulfonium, substituted H Y

YaH p-Me

CH

+SMe

2

(1) 1998CHE/LIU (2) 2000CHE/LIU

(continued)

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132

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.4 (continued) C–H BDEs with a-C(S), -S, -SO, -SO2 BDEs (boldfaceZrecommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

p-CN

(2) 86.0

359.8

p-MeO

(1) 84.6

354.0

p-MCO2

(2) 92.0

384.9

Methods (reference in parentheses)

References

Phenyl phenylsulphonyl methane, substituted H CH

Y

SO2Ph

YaH Me

90.3

377.8

89.1

372.8

Cl

91.8

384.1

Br

90.4

378.2

3.6.5

AOP

1998BOR/LIU

C–H BDEs with other heteroatoms at a-position

Table 3.6.5 C–H BDEs with Other Heteroatoms at a-Position

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

H X

H

XaP (phosphole)

%76.7

%320.9

As (arsole)

%76.7

%320.9

Ylide bromides K PhCHC 2 PðBuÞ3 Br

89.1

373

K PhCHC 2 PðPhÞ3 Br

88.7

371

K PhCHC 2 AsðBuÞ3 Br

91.8

384

K PhCHC 2 SeðMeÞ2 Br

88.4

370

K PhCHC 2 PðBuÞ2 Br

88.9

372

K PhCHC 2 TeðBuÞ2 Br

89.9

376

K PhCðOÞCHC 2 PðBuÞ3 Br

93.2

390

K PhCðOÞCHC 2 PðPhÞ3 Br

96.6

404

K PhCðOÞCHC 2 AsðPhÞ3 Br

95.8

401

K PhCðOÞCHC 2 SeðMeÞ2 Br

98.0

410

K PhCðOÞCHC 2 TeðBuÞ2 Br

97.3

407

GPA

1994SUN/PAN

AOP

1997CHE/LIU

7366—CHAPTER 3—6/2/2007—13:35—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

133

Ylide bromides FLHCP(Bu)3BrK

81.5

K PhCHC 2 PðPhÞ3 Br C PhCH2 AsðPhÞ3 BrK

81.6

341.5

82.6

345.6

2,2-Dimethyl-2-silapropane H–CH2SiMe3 DfH0(R)ZK7.6G1.5 (K32G6)

100G1.5

2,2,3,3-Tetramethyl-2-silabutane H–CH2C(CH3)2SiMe3 DfH0(R)ZK29.8 (K125)

340.8

AOP

1997LIU/HUA

418G6.3

Iodination

1998BEC/WAL

97.8G1.2

409G5

Iodination

1998BEC/WAL

Phenyl-trimethyl-silane H–CH2SiMe2Ph

98.0

410.1

Correlation

2002TUM/KRO

Bis(trimethylsilyl)methane H–CH((CH3)3Si)2

95G3

397G13

Electron photodetach.

1998ROM/GAT

Alkyldioxaborolanes H–CH2B(RO)2

98.6

412.5

EPR

2000WAL/MCC

Bis(dimethylphosphino)methane H–CH((CH3)2P)2

92G3

385G13

Electron photodetach.

1998ROM/GAT

Electrochemical

1999TRU/CAS

Electrochemical

1999TRU/CAS

Electrochemical

1999TRU/CAS

FLZfluorenyl

Organoferric species, FeII H–C bonds in a CH3 group FeII ðC5 H5 Þðh6 C6 Me6 ÞCPFK 6

86.5G1.5

362G6

FeII ðC5 Me5 Þðh6 C6 Me6 ÞCPFK 6

85.5G2

358G8

FeII ðC5 H5 Þðh6 C6 H5 CH2 C6 H5 ÞCPFK 6

84G2

351G8

FeII ðC5 H5 Þðh6 C6 H5 CHPh2 ÞCPFK 6

82.6G2

346G8

FeII ðC5 H5 Þðh6 fluoreneÞCPFK 6

81G2

339G8

FeII(C5H5)(h6-C6Me)

67.5G1.5

282G6

Organoferric species, FeI H–C bonds in a CH3 group FeI(C5Me5)(h6-C6Me6)

65.1G2

272G8

II

6

Fe (C5H5)(h -C6H5CH2C6H5)

59.4G1.5

249G6

FeII(C5H5)(h6-C6H5CHPh2)

58G1.5

243G6

FeII(C5H5)(h6-fluorene)

52.6G1.5

220G6

Organoferric species, Fe0 H–C bonds in a CH3 group Fe0(C5H5)(h6-C6Me6)K

68.2G2

285G8

Fe0(C5Me5)(h6-C6Me6)K

67.5G2

282G8

(continued)

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134

Comprehensive Handbook of Chemical Bond Energies

Table 3.6.5 (continued) C–H BDEs with Other Heteroatoms at a-Position BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Fe0(C5H5)(h6-C6H5CH2C6H5)K

59.6G2

249G8

Fe0(C5H5)(h6-C6H5CHPh2)K

59.3G2

248G8

Fe (C5H5)(h -fluorene)

44.1G2

185G8

Organoferric species, FeIII H–C bonds in a CH3 group FeIII(C5H5)(h6-C6Me6)2C

48.2G3

202G12

FeIII(C5Me5)(h6-C6Me6)2C

48.1G3

201G12

FeIII(C5H5)(h6-C6H5CH2C6H5)2C

48.5G3

203G12

FeIII(C5H5)(h6-C6H5CHPh2)2C

47G3

197G12

FeIII(C5H5)(h6-fluorene)2C

51G3

213G12

0

6

K

Methods (reference in parentheses)

Electrochemical

References

1999TRU/CAS

Note: (1) The BDEs in the clusters and complexes of C-, Si-, Ge-, Sn-, and Pb-ions are listed in Chapter 24. (2) The BDEs in the clusters and complexes of N-, P-, As-, Sb-, and Bi-ions are listed in Chapter 25. (3) The BDEs in the clusters and complexes of O-, S-, Se-, Te-, and Po-ions are listed in Chapter 26. (4) The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27.

3.7

C–H BDEs in radicals

Table 3.7 C–H BDEs in Radicals BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

reference in parentheses) kcal/mol

Methods (reference in

kJ/mol

parentheses)

References

Spectroscopy

1979HUB/HER

Derived from

2004RUS/BOG

Methylidyne C–H –D

Methylene

80.9G0.3

338.4G1.2

81.6

341.4

101.0G0.4

422.6G1.7

DfH0 in ref.

CH–H

Methyl radical

110.5G0.4

462.5G1.6

Ethyl radical

36.2G0.4

151.5G1.3

C%H2CH3

n-Propyl radical

Derived from

2004RUS/BOG

DfH0 in ref.

CH2–H

Derived from

1986PED/NAY

DfH0 in ref.

33.0G0.6

138.1G2.5

C%H2CH2CH3

7366—CHAPTER 3—6/2/2007—13:35—JEBA—15359—XML MODEL B – pp. 19–145

Derived from DfH0 in ref.

1986PED/NAY

BDEs of C–H Bonds

iso-Propyl radical

135

35.9G0.8

150.2G3.3

Derived from

CH3C%HCH3

n-Butyl radical

1986PED/NAY

DfH0 in ref.

33.5G0.6

140.2G2.5

Derived from

C%H2CH2CH2CH3

1986PED/NAY

DfH0 in ref.

iso-Butyl radical (CH3)2CHC%H2

31.4G1.0

131.4G4.2

Derived from DfH0 in ref.

1986PED/NAY

sec-Butyl radical

35.9G0.6

150.2G2.5

Derived from

1986PED/NAY

CH3C%HCH2CH3

tert-Butyl radical

DfH0 in ref.

36.6G0.8

153.1G3.3

Derived from

(CH3)2C%CH3

n-Pentyl radical

1986PED/NAY

DfH0 in ref.

34.0G1.0

142.3G4.2

Derived from

C%H2CH2CH2CH2CH3

1986PED/NAY

DfH0 in ref.

Pentyl-2 radical CH3CH2CH2C%HCH3

32.5G1.0

136.0G4.2

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-butyl-2 radical

35.1G1.0

146.9G4.2

Derived from

1986PED/NAY

CH3CH2C%(CH3)2

n-Hexyl radical

DfH0 in ref.

33.7G1.0

141.0G4.2

Derived from

C%H2CH2CH2CH2CH2CH3

1986PED/NAY

DfH0 in ref.

Hex-2-yl radical CH3C%HCH2CH2CH2CH3

32.2G1.2

134.7G5.0

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl pent-2-yl radical

36.3G2

151.9G8.4

Derived from

1986PED/NAY

C2H5CH2C%(CH3)2

3-Methyl pent-3-yl radical

DfH0 in ref.

35.1G2.5

146.9G10.5

Derived from

CH3CH2C%(CH3)(C2H5)

1986PED/NAY

DfH0 in ref.

(continued)

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136

Comprehensive Handbook of Chemical Bond Energies

Table 3.7 (continued) C–H BDEs in Radicals

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) Acetenyl radical %

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol 111.8G2.1

(reference in

kJ/mol

parentheses)

467.6G8.8

Derived from

References 1994GIN/FIN

DfH0 in ref.

CbC–H

Propargyl radical

Methods

100G5

418G21

GPA

1999WEN/LIN

87.3G4

365.3G16.7

Derived from

1999AHM/PET

H2CCC%KH

Carbene %%

DfH0 in ref.

CaCH–H

Vinyl radical

35.0G0.9

146.4G3.8

C%HaCH2

Derived from

1986PED/NAY

DfH0 in ref.

Vinyl radical

(1) 80.0G5

334.7G21

CH2C%–H

(2) 80.8G4

338.1G16.7

Allyl radical

56.8G0.8

237.7G3.3

CH2aCH-C%H2

Derived

(1) 1989ERV/HO (2) This volume

Derived from

1986PED/NAY

DfH0 in ref.

1-Propen-1-yl CH3CHaC%H

32.5G1.5

136.0G6.3

Derived from DfH0 in ref.

1986PED/NAY

1-Propen-2-yl

42.3G2

177.0G8.4

Derived from

1986PED/NAY

CH3-C%aCH2

1-Buten-4-yl radical

DfH0 in ref.

32.4G2.5

135.6G10.5

CH2CHCH2C%H2

Allyl radical

Derived from

1986PED/NAY

DfH0 in ref.

104.0G3.4

435.1G14.2

CH2CHC%H–H

7366—CHAPTER 3—6/2/2007—13:36—JEBA—15359—XML MODEL B – pp. 19–145

Derived

1997POU/NAS

BDEs of C–H Bonds

1-Butan-3-yl radical

137

75.7

316.5

Derived

2004JAN/ROS

74.9

313.3

Derived

2004JAN/ROS

32.6

136.2

Derived

2004JAN/ROS

90G2

377G8

Derived

1999WEN/HU

51.4G2.6

215.1G10.9

Derived from

1986PED/NAY

CHbC–%CHCH3

1,2-Butadien-4-yl radical CH2aCaCH–C%H2

1-Buten-3-yl radical CH2aCH–%CH–CH3

2-Methylallyl radical CH2C(CH3)C%H2

Cyclo-propyl radical H H

DfH0 in ref.

H

Cyclo-propyl methyl radical H

CH2

48.9G2

204.6G8.4

Derived from

1986PED/NAY

DfH0 in ref.

Cyclo-butyl radical H

H

38.2G1.5

159.8G6.3

Derived from

1986PED/NAY

DfH0 in ref.

H

1-Phenyl-cyclo-buten-3-yl radical 76G4.2

318.0G17.6

FT-MS

2005FAT/LIS

45.8G1.5

191.6G6.3

Derived from

1986PED/NAY

H

C6H5

Cyclo-pent-en-3-yl radical H

H

DfH0 in ref.

H

Cyclo-pentyl radical H H

H

34.9G1.5

146.0G6.3

Derived from DfH0 in ref.

1986PED/NAY

(continued)

7366—CHAPTER 3—6/2/2007—13:36—JEBA—15359—XML MODEL B – pp. 19–145

138

Comprehensive Handbook of Chemical Bond Energies

Table 3.7 (continued) C–H BDEs in Radicals

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in

kJ/mol

parentheses)

151.5G6.3

Derived from

References

2-Ethyl-cyclo-pentyl radical CH3

36.2G1.5

H

H

1986PED/NAY

DfH0 in ref.

Cyclo-hexa-1,3-dien-5-yl radical H

H H

24.2G1.5

101.3G6.3

Derived from DfH0 in ref.

1986PED/NAY

48.9G1.5

204.6G6.3

Derived from

1986PED/NAY

Cyclo-hexa-1-en-3-yl radical H

H

DfH0 in ref.

H

Cyclo-hexyl radical H

32.9G1.5

137.7G6.3

Derived from

1986PED/NAY

DfH0 in ref.

H H

1-Methyl-cyclo-hexyl radical CH3

36.3G1.5

151.9G6.3

Derived from DfH0 in ref.

1986PED/NAY

34.5G1.5

144.3G6.3

Derived from

1986PED/NAY

H H

1-Ethyl-cyclo-hexyl radical C2H5

DfH0 in ref.

H H

Cyclo-heptenyl radical H

46.1G1.5

192.9G6.3

H H

7366—CHAPTER 3—6/2/2007—13:37—JEBA—15359—XML MODEL B – pp. 19–145

Derived from DfH0 in ref.

1986PED/NAY

BDEs of C–H Bonds

139

Cyclo-heptyl radical H H

37.8G1.5

158.2G6.3

Derived from DfH0 in ref.

1986PED/NAY

31.4G1.5

131.4G6.3

Derived from

1986PED/NAY

H

Cyclo-octanyl radical H H

DfH0 in ref.

H

3,5-Didehydrophenyl radical 109.2G5.6

456.9G23.4

CID

2002LAR/NAS

78.3

327.6

Derived

1992GRA

105.2G3.5

440.2G14.6

Derived

1997POU/NAS

a-Methylbenzyl radical

(1) 45.1G2.0

188.7G8.4

H–CH2C%HPh

(2) 47.9

200.4

H

Phenyl radical C6H4–H

Benzyl radical C6H5C%H–H

(1) Der. from DfH0 in ref.

(1) 1996NIST (2) 2003TAN/PAP

(2) Kinetics

2-Naphthyl radical H H

7 6

H

H

8

1

5

4

H

H

2 3

C–H at 3 site 6 site

Fluoromethylene

H

77G4

322.2G16.7

107G4

447.7G16.7

78.9G3.8

330.1G15.9

Derived

2000REE/HAR

Derived from

1997POU/PAU

CF–H

DfH0 in ref.

(continued)

7366—CHAPTER 3—6/2/2007—13:37—JEBA—15359—XML MODEL B – pp. 19–145

140

Comprehensive Handbook of Chemical Bond Energies

Table 3.7 (continued) C–H BDEs in Radicals

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) Chloromethylene

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol 80.0G3.8

kJ/mol 334.7G15.9

Methods (reference in parentheses) Derived from

References 1997POU/PAU

DfH0 in ref.

CCl–H

Difluoromethyl radical CF2–H

65.7G2

274.9G8.4

Derived from DfH0 in ref.

1996NIST

Dichloromethyl radical

83.8G2

350.6G8.4

Derived

This volume

74.0G4

309.6G16.7

Derived

This volume

84.5G2.5

353.5G10.5

Derived

This volume

81.7G2

341.8G8.4

Derived

This volume

84.3G14

352.7G60

Derived

This volume

93.9G3.2

392.9G13.4

Derived from

This volume

CCl2–H

Chlorofluoromethyl radical CClF–H

Dibromomethyl radical CBr2–H

Bromochloromethyl radical CClBr–H

Diiodomethyl radical CI2–H

Fluoromethyl radical

DfH0 in ref.

CHF–H

Chloromethyl radical

102.1G2.5

427.2G10.5

Derived

This volume

69.2G2.5

289.5G10.5

Derived from DfH0 in ref.

1996NIST

CHCl–H

1,2-Difluoro-vin-1-yl radical CHFaC%F

7366—CHAPTER 3—6/2/2007—13:37—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

1,2-Dichloro-vin-1-yl radical

141

46.1G2.5

192.9G10.5

CHClaC%Cl

Derived from

1996NIST

DfH0 in ref.

1-Chloro-vin-1-yl radical CH2aC%Cl

43.2!

181!

Derived from DfH0 in ref.

1996NIST

1,1,2,2-Tetrafluoro-eth-1-yl radical

53.1G2.5

222.2G10.5

Derived from

1996NIST

CHF2C%F2

1,1,2-Trifluoro-eth-1-yl radical

DfH0 in ref.

46.3G2.5

193.7G10.5

CH2FC%F2

1,1-Difluoro-eth-1-yl radical

1996NIST

DfH0 in ref.

44.8G3

187.4G12.6

CH3C%F2

1,2,2-Trifluoro-eth-1-yl radical

Derived from

Derived from

1996NIST

DfH0 in ref.

47.8G2.5

200.0G10.5

CHF2C%HF

Derived from

1996NIST

DfH0 in ref.

1-Fluoro-eth-1-yl radical CH3C%HF

36.5G3

152.7G12.6

Derived from DfH0 in ref.

1996NIST

2,2-Difluoro-eth-1-yl radical

40.6G3

169.9G12.6

Derived from

1996NIST

CHF2C%H2

2-Fluoro-eth-1-yl radical

DfH0 in ref.

33.9G3

141.8G12.6

CH2FC%H2

1,1,2,2-Tetrachloro-eth-1-yl radical

1996NIST

DfH0 in ref.

43.5G3

182.0G12.6

CHCl2C%Cl2

1,1,2-Trichloro-eth-1-yl radical

Derived from

Derived from

1996NIST

DfH0 in ref.

41.2G3

172.4G12.6

CH2ClC%Cl2

Derived from

1996NIST

DfH0 in ref.

(continued)

7366—CHAPTER 3—6/2/2007—13:37—JEBA—15359—XML MODEL B – pp. 19–145

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Comprehensive Handbook of Chemical Bond Energies

Table 3.7 (continued) C–H BDEs in Radicals

The broken bonds (boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) 1,1-Dichloro-eth-1-yl radical

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol 37.3G3

kJ/mol 156.1G12.6

CH3C%Cl2

Methods (reference in parentheses) Derived from

References 1996NIST

DfH0 in ref.

1,2,2-Trichloro-eth-1-yl radical CHCl2C%HCl

36.4G3

152.3G12.6

Derived from DfH0 in ref.

1996NIST

1,2-Dichloro-eth-1-yl radical

36.9G3

154.4G12.6

Derived from

1996NIST

CH2ClC%HCl

1-Chloro-eth-1-yl radical

DfH0 in ref.

38.8G3

162.3G12.6

CH3C%HCl

2,2-Dichloro-eth-1-yl radical

31.1G2

130.1G8.4

34.9G2

146.0G8.4

40.7G2

170.3G8.4

38.7G2

161.9G8.4

1996NIST

Derived from

1996NIST

Derived from

1996NIST

DfH0 in ref.

35.8G2

149.8G8.4

CH3CH2C%HCl

2-Chloro-pro-2-yl radical CH3CC%ClCH3

Derived from

DfH0 in ref.

CH2BrC%H2

1-Chloro-pro-1-yl radical

1996NIST

DfH0 in ref.

CH3C%HBr

2-Bromo-eth-1-yl radical

Derived from DfH0 in ref.

CH2ClC%H2

1-Bromo-eth-1-yl radical

1996NIST

DfH0 in ref.

CHCl2C%H2

2-Chloro-eth-1-yl radical

Derived from

Derived from

1996NIST

DfH0 in ref.

39.1G2

163.6G8.4

7366—CHAPTER 3—6/2/2007—13:38—JEBA—15359—XML MODEL B – pp. 19–145

Derived from DfH0 in ref.

1996NIST

BDEs of C–H Bonds

143

C%H2CH2CH2Br

34.8G2

145.6G8.4

CH3C%HCH2Br

40.4G2.5

169.0G10.5

CH3C%HCH2Br

39.5G2.5

165.3G10.5

HOCH2C%H2

29.3G2.5

122.6G10.5

Derived from

1996NIST

DfH0 in ref.

Derived from

1996NIST

DfH0 in ref.

CH3C%HOH

81G4

339G17

Derived

This volume

CH3C%HOH

35.6G2.5

149.0G10.5

Derived from

1996NIST

C%H2CH2OH CH3CH2C%HOH

31.0G2.5 31.1G2.5

129.7G10.5 130.1G10.5

DfH0 in ref.

CH3C%HCH2OH

30.5G2.5

127.6G10.5

C%H2CH2CH2OH

38.6G3

161.5G12.6

(CH3)C%(CH3)OH

36.6G3

153.1G12.6

C%H2CH(OH)CH3

25.0G3

104.6G12.6

C2H5OC%HCH3

38.0G3

159.0G12.6

HOCH2C%HOH

29.2G3

122.2G12.6

C%H2OD

78.4G2.3

328.0G9.6

PD

2004FEN/DEM

HC%(O)

15.10G0.11

63.18G0.46

Derived

1997BEC/CAR

CH3C%(O)

33.7G2

141.0G8.4

Derived from

1996NIST

DfH0 in ref.

C%H2C(O)H CH3C%HC(O)OH

28.8G2 41.6G3

120.5G8.4 174.1G12.6

Derived from DfH0 in ref.

1996NIST

CH3O%

21.1G1

88.3G4

Derived from

1996NIST

CHCl2O%

7.2G2.4

30.1G10

CH2aCHO%

26.8G0.5

112.1G2

CH3CH2O%

14.5G1

60.7G4

DfH0 in ref.

(continued)

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144

Comprehensive Handbook of Chemical Bond Energies

Table 3.7 (continued) C–H BDEs in Radicals BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom), DfH0(R), kcal/mol (kJ/mol) CH3CH2CH2O%

kcal/mol 14.2G2

kJ/mol 59.4G8

Methods (reference in parentheses) Derived from

References 1996NIST

DfH0 in ref.

(CH3)2CHO%

11.8G1

49.4

Derived from

1986PED/NAY

DfH0 in ref.

CH3CH2CH2CH2O%

16.5G2

69.0G8

Derived from

1996NIST

DfH0 in ref.

C2H5CH(CH3)O%

11.7G1

49.0G4

C6H5CH2O%

17.7G3

74.1G12.6

H–C(O)O%

K11.0G3

K46.0G12.6

Derived from

1986PED/NAY

DfH0 in ref.

Derived from

1995KIN/BRA

DfH0 in ref.

H–CH2C%(CH3)C(O)OCH3

45.6

190.8

H–CH(R)C%(CH3)C(O)OCH3

46.1

192.9

H–CHN

23G6, at 0 K

H–HCNN

Kinetics

2003TAN/PAP

96G25

PES

1991COW/TRA

97G2

405.8G8.4

PES

1998CLI/WEN(b)

CH3C%HNH2

36.6G3

153.1G12.6

Derived from

1996NIST

CH3C%HCN

40.9G3

171.1G12.6

DfH0 in ref.

C%H2CH2CN NCC%HCH2CN

36.4G3 42.1G4

152.3G12.6 176.1G16.7

7366—CHAPTER 3—6/2/2007—13:38—JEBA—15359—XML MODEL B – pp. 19–145

BDEs of C–H Bonds

145

H–C%(S)

47.3G3

197.9G12.6

Derived

This volume

H–C%H2S

50.6G2.0

211.7G8.4

Derived

This volume

H–C%P

119.1, at 0 K

498.2

Spectroscopy

1993MAS/LEH

Note: (1) The BDEs in the clusters and complexes of C-, Si-, Ge-, Sn-, and Pb-ions are listed in Chapter 24. (2) The BDEs in the clusters and complexes of N-, P-, As-, Sb-, and Bi-ions are listed in Chapter 25. (3) The BDEs in the clusters and complexes of O-, S-, Se-, Te-, and Po-ions are listed in Chapter 26. (4) The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27.

7366—CHAPTER 3—6/2/2007—13:38—JEBA—15359—XML MODEL B – pp. 19–145

chapter four

BDEs of C–C bonds 4.1

Saturated hydrocarbons

Table 4.1 C–C BDEs in Saturated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

Ethane CH3–CH3

90.2G0.2

377.4G0.8

Derived from DfH0 in ref.

1986PED/NAY

Propane CH3–C2H5

88.5G0.5

370.3G2.1

Derived from DfH0 in ref.

1986PED/NAY

Butane CH3–nC3H7

88.9G0.7

372.0G2.9

Derived from DfH0 in ref.

1986PED/NAY

Iso-butane CH3–iso-C3H7

88.2G0.9

369.0G3.8

Derived from DfH0 in ref.

1986PED/NAY

Pentane CH3–nC4H9

88.8G0.7

371.5G2.9

Derived from DfH0 in ref.

1986PED/NAY

3-Methylbutane CH3–iso-C4H9

88.5G1.1

370.3G4.6

Derived from DfH0 in ref.

1986PED/NAY

References

(continued)

147

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Comprehensive Handbook of Chemical Bond Energies

Table 4.1 (continued) C–C BDEs in Saturated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

2-Methylbutane CH3–sec-C4H9

88.0G0.7

368.2G2.9

Derived from DfH0 in ref.

1986PED/NAY

2,2-Dimethylpropane CH3–tert-C4H9

86.9G0.7

363.6G2.9

Derived from DfH0 in ref.

1986PED/NAY

Hexane CH3–nC5H11

88.1G1.5

368.4G6.3

Derived from DfH0 in ref.

1996NIST

2-Methylpentane CH3–CH(CH3)C3H7

88.9G1.0

372.0G4.2

Derived from DfH0 in ref.

1986PED/NAY

3-Methylpentane CH3–CH(C2H5)2

87.4G1.0

365.7G4.2

Derived from DfH0 in ref.

1986PED/NAY

2,2,-Dimethyl-butane CH3–C(CH3)2(CH2CH3)

86.3G1.5

360.9G6.3

Derived from DfH0 in ref.

1996NIST

Heptane CH3–nC6H13

88.0G1.5

368.2G6.3

Derived from DfH0 in ref.

1996NIST

Butane C2H5–C2H5

86.8G0.6

363.2G2.5

Derived from DfH0 in ref.

1986PED/NAY

Pentane C2H5–nC3H7

87.3G0.7

365.3G2.9

Derived from DfH0 in ref.

1986PED/NAY

iso-Pentane C2H5–iso-C3H7

86.1G0.9

360.2G3.8

Derived from DfH0 in ref.

1986PED/NAY

7366—CHAPTER 4—5/2/2007—20:03—BSARAVANAN—15360—XML MODEL B – pp. 147–210

References

BDEs of C–C Bonds

149

Hexane C2H5–nC4H9

86.9G0.8

363.6G3.3

Derived from DfH0 in ref.

1986PED/NAY

2-Methylpentane C2H5–iso-C4H9

86.9G1.3

363.6G5.4

Derived from DfH0 in ref.

1986PED/NAY

3-Methylpentane C2H5–sec-C4H9

85.7G0.8

358.6G3.3

Derived from DfH0 in ref.

1986PED/NAY

2,2-Dimethylbutane C2H5–tert-C4H9

84.5G0.9

353.5G3.8

Derived from DfH0 in ref.

1986PED/NAY

Heptane C2H5–nC5H11

86.3G1.5

361.0G6.3

Derived from DfH0 in ref.

1988NIST

Octane C2H5–nC6H13

86.2G1.5

360.7G6.3

Derived from DfH0 in ref.

1988NIST

3-Ethyl-pentane C2H5–CH(CH2CH3)2

85.0G1.5

355.4G6.3

Derived from DfH0 in ref.

1988NIST

3,3-Dimethyl-pentane C2H5–C(CH3)2(CH2CH3)

83.5G1.5

349.2G6.3

Derived from DfH0 in ref.

1988NIST

2-Methylpentane C3H7–iso-C3H7

86.6G1.3

362.3G5.4

Derived from DfH0 in ref.

1986PED/NAY

Hexane nC3H7–nC3H7

87.5G0.8

366.1G3.3

Derived from DfH0 in ref.

1986PED/NAY

2-Methylpentane nC3H7–iso-C3H7

86.6G1.0

362.3G4.2

Derived from DfH0 in ref.

1986PED/NAY

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 4.1 (continued) C–C BDEs in Saturated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

Heptane nC3H7–nC4H9

87.3G0.9

365.3G3.8

Derived from DfH0 in ref.

1986PED/NAY

2-Methylhexane nC3H7–iso-C4H9

84.2G1.3

352.3G5.4

Derived from DfH0 in ref.

1986PED/NAY

3-Methylhexane nC3H7–sec-C4H9

85.7G0.9

358.6G3.8

Derived from DfH0 in ref.

1986PED/NAY

2,2-Dimethylpentane nC3H7–tert-C4H9

84.6G1.0

354.0G4.2

Derived from DfH0 in ref.

1986PED/NAY

2,3-Dimethylbutane iso-C3H7–iso-C3H7

84.5G1.1

353.5G4.6

Derived from DfH0 in ref.

1986PED/NAY

2-Methylhexane iso-C3H7–nC4H9

86.1G1.1

360.2G4.6

Derived from DfH0 in ref.

1986PED/NAY

2,4-Dimethylpentane iso-C3H7–iso-C4H9

85.9G1.3

359.4G5.4

Derived from DfH0 in ref.

1986PED/NAY

2,3-Dimethylpentane iso-C3H7–sec-C4H9

84.7G1.0

354.4G4.2

Derived from DfH0 in ref.

1986PED/NAY

2,2,3-Trimethylbutane iso-C3H7–tert-C4H9

81.5G1.1

341.0G4.6

Derived from DfH0 in ref.

1986PED/NAY

Octane nC3H7–nC5H11

86.7G1.5

362.8G6.3

Derived from DfH0 in ref.

1986PED/NAY

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References

BDEs of C–C Bonds

151

2-Methyl-heptane iso-C3H7–nC5H11

85.5G1.5

357.7G6.3

Derived from DfH0 in ref.

1996NIST

2,3-Dimethyl-hexane iso-C3H7–CH(CH3)(C3H7)

84.1G1.5

352.0G6.3

Derived from DfH0 in ref.

1996NIST

3-Ethyl-hexane nC3H7–CH(CH2CH3)2

85.5G1.5

357.7G6.3

Derived from DfH0 in ref.

1996NIST

3-Ethyl-2-methyl-pentane iso-C3H7–CH(CH2CH3)2

82.7G1.5

345.9G6.3

Derived from DfH0 in ref.

1996NIST

2,2,3-Trimethyl-penane iso-C3H7–CH2C(CH3)3

83.3G1.5

348.4G6.3

Derived from DfH0 in ref.

1996NIST

2,3,3-Trimethyl-penane iso-C3H7–C(CH3)2 (CH2CH3)

79.6G1.5

333.2G6.3

Derived from DfH0 in ref.

1996NIST

Octane nC4H9–nC4H9

87.0G0.9

364.0G3.8

Derived from DfH0 in ref.

1986PED/NAY

2-Methylheptane nC4H9–iso-C4H9

86.8G1.3

363.2G5.4

Derived from DfH0 in ref.

1986PED/NAY

3-Methylheptane nC4H9–sec-C4H9

85.6G0.9

358.2G3.8

Derived from DfH0 in ref.

1986PED/NAY

2,2-Dimethylhexane nC4H9–tert-C4H9

83.9G1.0

351.0G4.2

Derived from DfH0 in ref.

1986PED/NAY

2,5-Dimethylhexane iso-C4H9–iso-C4H9

86.6G1.5

362.3G6.3

Derived from DfH0 in ref.

1986PED/NAY

(continued)

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Table 4.1 (continued) C–C BDEs in Saturated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

2,4-Dimethylhexane iso-C4H9–sec-C4H9

85.3G1.3

356.9G5.4

Derived from DfH0 in ref.

1986PED/NAY

2,3,4-trimethylpentane iso-C4H9–tert-C4H9

81.3G1.3

340.2G5.4

Derived from DfH0 in ref.

1986PED/NAY

3,4-Dimethylhexane sec-C4H9–sec-C4H9

83.3G0.8

348.5G3.3

Derived from DfH0 in ref.

1986PED/NAY

2,2,3-Trimethylpentane sec-C4H9–tert-C4H9

80.4G1.0

336.4G4.2

Derived from DfH0 in ref.

1986PED/NAY

2,2,3,3-Tetramethylbutane tert-C4H9–tert-C4H9

77.1G1.0

322.6G4.2

Derived from DfH0 in ref.

1986PED/NAY

2,3-Trimethylpentane iso-C3H7–C(CH3)2C2H5

79.7G1.5

333.5G6.3

Derived from DfH0 in ref.

1986PED/NAY

Nonane nC4H9–nC5H11

86.1G2.0

360.2G8.4

Derived from DfH0 in ref.

1986PED/NAY

2,2-Dimethylheptane nC4H9–neo-C5H11

81.8G2.0

342.3G8.4

Derived from DfH0 in ref.

1994PED

2,2,5-Trimethylhexane iso-C4H9–neo-C5H11

85.9G2.0

359.4G8.4

Derived from DfH0 in ref.

1994PED

2,2,3,3-Tetramethylpentane tert-C4H9–C(CH3)2C2H5

75.3G1.5

315.1G6.3

Derived from DfH0 in ref.

1986PED/NAY

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References

BDEs of C–C Bonds

153

2,2,4,4-Tetramethypentane tert-C4H9–neo-C5H11

77.9G2.2

326.0G9.2

Derived from DfH0 in ref.

1986PED/NAY

2-Methylnonane nC6H13–iso-C4H9

86.8G2.0

363.2G8.4

Derived from DfH0 in ref.

1986PED/NAY

5-Methylnonane nC4H9–CH(CH3)(nC4H9)

87.4G2.0

365.7G8.4

Derived from DfH0 in ref.

1986PED/NAY

Dodecane nC6H13–nC6H13

85.0G2.0

355.6G8.4

Derived from DfH0 in ref.

1986PED/NAY

Methyl-cyclo-pentane CH3–cyclo-C5H9

85.6G1.2

358.2G5.0

Derived from DfH0 in ref.

1986PED/NAY

Methyl-cyclo-hexane CH3–cyclo-C6H11

90.1G1.8

377.0G7.5

Derived from DfH0 in ref.

1986PED/NAY

Ethyl-cyclo-butane C2H5–cyclo-C4H7

86.1G1.3

360.2G5.4

Derived from DfH0 in ref.

1986PED/NAY

Ethyl-cyclo-pentane C2H5–cyclo-C5H9

84.0G1.3

351.5G5.4

Derived from DfH0 in ref.

1986PED/NAY

Ethyl-cyclo-hexane C2H5–cyclo-C6H11

87.4G1.3

365.7G5.4

Derived from DfH0 in ref.

1986PED/NAY

Propyl-cyclo-pentane nC3H7–cyclo-C5H9

84.4G1.3

353.1G5.4

Derived from DfH0 in ref.

1986PED/NAY

Propyl-cyclo-hexane nC3H7–cyclo-C6H11

87.8G2.0

367.4G8.4

Derived from DfH0 in ref.

1986PED/NAY

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 4.1 (continued) C–C BDEs in Saturated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

Butyl-cyclo-hexane nC4H9–cyclo-C6H11

85.3G1.5

356.9G6.3

Derived from DfH0 in ref.

1986PED/NAY

Cyclo-hexaxyl-cyclohexane cyclo-C6H11–cyclo-C6H11

88.2G2.0

369.0G8.4

Derived from DfH0 in ref.

1988LIA/BAR

(1) 89.2G3

373.2G12.6

(1) 2000MEL/PIM

(2) 82.5

345.3

(1) Derived from DfH0 in ref. (2) Derived

2-Me

(1) 87.3G3

365.3G12.6

1-Et

(1) 86.1G3 (2) 80.3

360.2G12.6 336.0

References

Adamantyl compounds R 1 2

RZ1-Me

4.2

(2) 2002MIR/LEB

Chain unsaturated hydrocarbons

Table 4.2 C–C BDEs in Chain Unsaturated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Acetylene CHbCH

228.0G1.0

954.0G4.2

Derived from DfH0 in ref.

1986PED/NAY

Ethylene CH2aCH2

174.1G1.5

728.4G6.3

Derived from DfH0 in ref.

1986PED/NAY

Propyne CH3–CbCH

126.5G1.0

529.3G4.2

Derived from DfH0 in ref.

1986PED/NAY

7366—CHAPTER 4—5/2/2007—20:03—BSARAVANAN—15360—XML MODEL B – pp. 147–210

BDEs of C–C Bonds

155

Buta-1,3-diyne HCbC–CbCH

160.2G2.0

670.3G8.4

Derived from DfH0 in ref.

1996NIST

But-1-en-3-yne H2CaC–CbCH

136.8G2.5

572.4G10.5

Derived from DfH0 in ref.

1996NIST

1-Butyne C2H5–CbCH

124.5G1.0

520.9G4.2

Derived from DfH0 in ref.

1986PED/NAY

1-Butyne CH3–CH2CbCH

(1) 76.0G2 (2) 76.6G1.2

318.0G8.4 320.5G5.0

(1) VLPP (2) Der. from DfH0 in ref.

(1) 1978KIN (2) 1986PED/NAY

2-Butyne CH3–CbCCH

121.8G3.2

509.6G13.4

Derived from DfH0 in ref.

1986PED/NAY

2-Pentyne CH3–CH2CbCCH3

73.7G1.5

308.4G6.3

VLPP

1982NGU/KIN

2-Methy-1-butyne CH3–CH(CH3)CbCH

73G2

305.4G8.4

VLPP

1981NGU/KIN

2-Methy-1-pentyne CH3–CH(CH3)CbCCH3

76.7G1.5

320.9G6.3

VLPP

1981KIN/NGU

2,2-Dimethy-1-butyne CH3–C(CH3)2CbCH

70.7G1.5

295.8G6.3

VLPP

1977KIN

2,2-Dimethy-1-pentyne CH3–C(CH3)2CbCCH3

72.5G1.5

303.3G6.3

VLPP

1981KIN/NGU

1-Hexyne nC3H7–CH2CbCH

73.2G1.5

306.3G6.3

VLPP

1981KIN

(continued)

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156

Comprehensive Handbook of Chemical Bond Energies

Table 4.2 (continued) C–C BDEs in Chain Unsaturated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

2-Ethyl-1-pentyne sec-C4H9–CH2CbCH

71.7G1.5

300.0G6.3

SPTS

1978TSA

Propene CH3–CHCH2

101.9G1.5

426.3G6.3

Derived from DfH0 in ref.

1986PED/NAY

1,2-Butadiene CH3–CHaCCH2

86.0G1.4

359.8G5.9

Derived from DfH0 in ref.

1986PED/NAY

1,3-Butadiene C2H3–CHaCH2

116.9G1.5

489.1G6.3

Derived from DfH0 in ref.

1986PED/NAY

1-Methylcyclopropene CH3–cyclopro-en-1-yl

81.4G5

340.6G20.9

Derived from DfH0 in ref.

1986PED/NAY

1-Butene CH3–CH2CHaCH2

(1) 76.5G2.2 (2) 75.9G0.9

320.1G9.2 317.6G3.8

(1) VLPP (2) Der. from DfH0 in ref.

(1) 1981NGU/KIN (2) 1986PED/NAY

1-Butene C2H5–CHaCH2

100.0G1.0

418.4G4.2

Derived from DfH0 in ref.

1986PED/NAY

1,3-Butadiene, 2-methyl CH2C(CH3)–CHCH2

108.8G2

455.2G8.4

Derived from DfH0 in ref.

1996NIST

(E)-2-Butene (E)-CH3–CHaCHCH3

101.6G2.0

425.1G8.4

Derived from DfH0 in ref.

1986PED/NAY

(Z)-2-Butene (Z)-CH3–CHaCHCH3

102.6G2.0

429.3G8.4

Derived from DfH0 in ref.

1986PED/NAY

7366—CHAPTER 4—5/2/2007—20:03—BSARAVANAN—15360—XML MODEL B – pp. 147–210

BDEs of C–C Bonds

157

1,2-Pentadiene C2H5–CHaCaCH2

80.6G1.5

337.2G6.3

Derived from DfH0 in ref.

1986PED/NAY

1,4-Pentadiene C2H3–CH2CHaCH2

87.2G1.2

364.8G5.0

Derived from DfH0 in ref.

1986PED/NAY

(E)-1,3-Pentadiene (E)-CH2aCH–CHa CHCH3

117.2G2.0

490.4G8.4

Derived from DfH0 in ref.

1986PED/NAY

(Z)-1,3-Pentadiene (Z)-CH2aCH–CHa CHCH3

118.5G2.0

495.8G8.4

Derived from DfH0 in ref.

1986PED/NAY

1-Pentene C2H5–CH2CHaCH2

74.3G1.5

310.9G6.3

Derived from DfH0 in ref.

1986PED/NAY

(E)-2-Pentene (E)-CH3–CH2CHaCHCH3

77.6G2.2

324.7G9.2

Derived from DfH0 in ref.

1986PED/NAY

(Z)-2-Pentene (Z)-CH3–CH2CHaCHCH3

78.6G2.2

328.9G9.2

Derived from DfH0 in ref.

1986PED/NAY

2-Pentene C2H5–CHaCHCH3

99.8G2.0

417.6G8.4

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-1-butene CH3–CH2C(CH3)aCH2

(1) 72.0G2 (2) 74.1G1.0

301.2G8.4 310.0G4.2

(1) Kinetics (2) Der. from DfH0 in ref.

(1) 1981STE/ROW (2) 1986PED/NAY

3-Methyl-1-butene CH3–CH(CH3)CHaCH2

72.3G1.5

302.5G6.3

Derived from DfH0 in ref.

1986PED/NAY

(continued)

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158

Comprehensive Handbook of Chemical Bond Energies

Table 4.2 (continued) C–C BDEs in Chain Unsaturated Hydrocarbons BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated group)

kcal/mol

3,3-Dimethyl-1-butene CH3–C(CH3)2CHaCH2

(1) 68.1G1.5 (2) 67.5G1.5

284.9G6.3 282.4G6.3

(1) Derived (2) Der. from DfH0 in ref.

(1) 1982MCM/GOL (2) 1986PED/NAY

2-Methyl-1-butene C2H5–C(CH3)aCH2

92.1G2

385.3G8.4

Derived from DfH0 in ref.

1996NIST

3-Methyl-1-butene iso-C3H7–CHaCH2

99.2G1.5

415.1G6.3

Derived from DfH0 in ref.

1986PED/NAY

2,3-Dimethyl-1-butene iso-C3H7–C(CH3)aCH2

92.0G2

384.9G8.4

Derived from DfH0 in ref.

1996NIST

1,5-Hexadiene C3H5–C3H5

61.5G1.0

257.3G4.2

Derived from DfH0 in ref.

1986PED/NAY

1-Hexene nC3H7–CH2CHaCH2

(1) 70.7G2 (2) 75.0G1.0

295.8G8.4 313.8G4.2

(1) SPST (2) Der. from DfH0 in ref.

(1) 1976TSA(b) (2) 1986PED/NAY

1-Hexene nC4H9–CHaCH2

100.6G1.3

420.9G5.4

Derived from DfH0 in ref.

1986PED/NAY

(E)-2-Hexene (E)-C2H5–CH2CHa CHCH3

76.2G2.4

318.8G10.0

Derived from DfH0 in ref.

1986PED/NAY

(Z)-2-Hexene (Z)-C2H5–CH2CHa CHCH3

76.6G2.4

320.5G10.0

Derived from DfH0 in ref.

1986PED/NAY

kJ/mol

Methods (reference in parentheses)

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References

BDEs of C–C Bonds

159

2-Hexene C3H7–CHaCHCH3

100.5G2.0

420.5G8.4

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-1-pentene C2H5–CH2C(CH3)aCH2

73.2G1.0

306.3G4.2

Derived from DfH0 in ref.

1986PED/NAY

3-Methyl-1-pentene C2H5–CH(CH3)CHaCH2

70.8G1.5

296.2G6.3

Derived from DfH0 in ref.

1986PED/NAY

3-Methyl-1-pentene sec-C4H9–CHaCH2

99.6G1.0

416.7G4.2

Derived from DfH0 in ref.

1986PED/NAY

4-Methyl-1-pentene iso-C3H7–CH2CHaCH2

74.1G1.0

310.0G4.2

Derived from DfH0 in ref.

1986PED/NAY

4-Methyl-1-pentene iso-C4H9–CHaCH2

100.6G1.5

420.9G6.3

Derived from DfH0 in ref.

1986PED/NAY

(E)-4-Methyl-2-pentene (E)-iso-C3H7–CHaCHCH3

99.5G2.0

416.3G8.4

Derived from DfH0 in ref.

1986PED/NAY

(Z)-4-Methyl-2-pentene (Z)-iso-C3H7–CHaCHCH3

100.5G2.0

420.5G8.4

Derived from DfH0 in ref.

1986PED/NAY

3,3-Dimethyl-1-butene tert-C4H9–CHaCH2

97.7G1.3

408.8G5.4

Derived from DfH0 in ref.

1986PED/NAY

1-Heptene nC4H9–CH2CHaCH2

74.3G1.0

310.9G4.2

Derived from DfH0 in ref.

1986PED/NAY

1-Heptene nC5H11–CHaCH2

99.5G1.5

416.3G6.3

Derived from DfH0 in ref.

1986PED/NAY

(continued)

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Table 4.2 (continued) C–C BDEs in Chain Unsaturated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

5-Methyl-1-hexene iso-C4H9–CH2CHaCH2

73.2G1.5

306.3G6.3

Derived from DfH0 in ref.

1986PED/NAY

5-Methyl-1-hexene nC3H7–CH2C(CH3)aCH2

70.1G1.6

293.3G6.7

Derived from DfH0 in ref.

1986PED/NAY

2,4-Dimethyl-1-pentene iso-C3H7–CH2C(CH3)aCH2

71.6G1.5

299.6G6.3

Derived from DfH0 in ref.

1986PED/NAY

4,4-Dimethyl-1-pentene tert-C4H9–CH2CHaCH2

71.9G1.5

300.8G6.3

Derived from DfH0 in ref.

1986PED/NAY

(E)-4,4-Dimethyl-2-pentene (E)-tert-C4H9–CHaCHCH3

96.6G2.0

404.2G8.4

Derived from DfH0 in ref.

1986PED/NAY

(Z)-4,4-Dimethyl-2-pentene (Z)-tert-C4H9–CHaCHCH3

100.5G2.0

420.5G8.4

Derived from DfH0 in ref.

1986PED/NAY

2,4,4-Trimethyl-1-pentene tert-C4H9–CH2C(CH3)a CH2

68.6G2.0

287.0G8.4

Derived from DfH0 in ref.

1986PED/NAY

1-Octene nC5H11–CH2CHaCH2

73.3G1.5

306.7G6.3

Derived from DfH0 in ref.

1986PED/NAY

Cyclo-pentene, 3-methyl CH3–cyclo–C5H7

71.5G2

299.2G8.4

Derived from DfH0 in ref.

1996NIST

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BDEs of C–C Bonds

161

3-Cyclo-pentylpropene cyclo-pentyl–CH2CHCH2

71.9G1.5

300.8G6.3

Derived from DfH0 in ref.

1986PED/NAY

Vinyl-cyclo-hexane cyclo-hexayl–CHCH2

91.3G2.0

382.0G8.4

Derived from DfH0 in ref.

1986PED/NAY

4.3

Aromatic hydrocarbons

Table 4.3 C–C BDEs in Aromatic Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

References

Methylbenzene CH3–C6H5

102.0G1.0

426.8G4.2

Derived from DfH0 in ref.

1986PED/NAY

Phenylacetylene HCC–C6H5

141.2G1.4

590.8G5.9

Derived from DfH0 in ref.

1996NIST

Vinylbenzene C2H3–C6H5

115.2G1.3

482.0G5.4

Derived from DfH0 in ref.

1986PED/NAY

(1) 74.1 (2) 75.8G1 (3) 77.7G1.0

310.0 317.1 325.1G4.2

(1) 1980BAR/STE (2) 1982MCM/GOL (3) 1986PED/NAY

(1) 72.9

305.0

(1) VLPP (2) Derived (3) Der. from DfH0 in ref. (4) VLPP

(4) 1986ROB/STE

Derived from DfH0 in ref.

1986PED/NAY

Ethylbenzene, substituted CH 3 Y

YZH

2-Me 3-Me

(1) 73.8

308.8

4-CH2aCH

(4) 70.6

295.4

2,6-Me2

(1) 71.2

297.9

3,6-Me2

(1) 72.5

303.3

3,5-Me2

(1) 73.5

307.5

100.2G1.0

419.2G4.2

Ethylbenzene C2H5–C6H5

(continued)

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Table 4.3 (continued) C–C BDEs in Aromatic Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

Cyclo-propylbenzene cyclo-C3H5–C6H5

109.8G1.2

459.4G5.0

Derived from DfH0 in ref.

1986PED/NAY

Prop-2-enylbenzene C2H3–CH2C6H5

89.2

373.2

Derived from DfH0 in ref.

1999VER(c)

Propylbenzene C2H5–CH2C6H5

76.2G1.5

318.8G6.3

Derived from DfH0 in ref.

1986PED/NAY

Prop-2-enylbenzene C2H3CH2–C6H5

87.6

366.5

Derived from DfH0 in ref.

1999VER(c)

Propylbenzene nC3H7–C6H5

100.8G1.0

421.7G4.2

Derived from DfH0 in ref.

1986PED/NAY

iso-Propylbenzene CH3–CH(CH3)C6H5

(1) 73.8 (2) 74.6G1.5 (3) 76.2G2.0

308.8 312.1G6.3 318.8G8.4

(1) VLPP (2) Re-cal. (3) Der. from DfH0 in ref.

(1) 1981ROB/STE (2) 1984ROS/MCM (3) 1996NIST

iso-Propylbenzene iso-C3H7–C6H5

98.9G1.2

413.8G5.0

Derived from DfH0 in ref.

1986PED/NAY

Butylbenzene nC4H9–C6H5

100.6G1.0

420.9G4.2

Derived from DfH0 in ref.

1986PED/NAY

Butylbenzene nC3H7–CH2C6H5

76.6G1.5

320.5G6.3

Derived from DfH0 in ref.

1986PED/NAY

4-Phenyl-1-butene CH2aCHCH2–CH2C6H5

61.4G2

256.9G8.4

VLPP

1979KIN/NGU

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References

BDEs of C–C Bonds

163

2-Methyl-1-phenylpropane iso-C3H7–CH2C6H5

75.8G1.5

317.1G6.3

Derived from DfH0 in ref.

1986PED/NAY

2-Methylpropylbenzene iso-C4H9–C6H5

100.7G1.5

421.3G6.3

Derived from DfH0 in ref.

1986PED/NAY

tert-Butylbenzene tert-C4H9–C6H5

95.8G1.5

400.8G6.3

Derived from DfH0 in ref.

1986PED/NAY

4-Phenyl-1-butyne C6H5CH2–CH2CbCH

61.4G2

256.9G8.4

VLPP

1979KIN/NGU

2-Phenylbutane C2H5–CH(CH3)C6H5

(1) 73.7G1.5 (2) 74.6G2.0

308.4G6.3 312.1G8.4

(1) VLPP (2) Der. from DfH0 in ref.

(1) 1981ROB/STE (2) 1996NIST

tert-Butylbenzene CH3–C(CH3)2C6H5

72.5G2.0

303.3G8.4

Derived from DfH0 in ref.

1986PED/NAY

((1Z)-Prop-1-enyl)benzene CH3–CH2CHCHC6H5

70.6

295.4

VLPP

1986ROB/STE

1,1-Diphenylethane CH3–CH(C6H5)2

(1) 71.3 (2) 75.5G1.5

298.3 315.9G6.3

(1) VLPP (2) Der. from DfH0 in ref.

(1) 1984ROS/MCM (2) 1999VER(d)

2-Methyl-1,1diphenylpropane iso-C3H7–CH(C6H5)2

73.6G1.5

307.9G6.3

Derived from DfH0 in ref.

1999VER(d)

2,2-Diphenylpropane CH3–C(CH3)(C6H5)2

69.5G2

290.8G8.4

VLPP

1981STE (continued)

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Table 4.3 (continued) C–C BDEs in Aromatic Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

Biphenyl C6H5–C6H5

114.4G1.5

478.6G6.3

Derived from DfH0 in ref.

1986PED/NAY

Diphenylmethane C6H5–CH2C6H5

91.7G2.0

383.7G8.4

Derived from DfH0 in ref.

1986PED/NAY

Bibenzyl C6H5CH2–CH2C6H5

65.2G2.2

272.8G9.2

Derived from DfH0 in ref.

1986PED/NAY

Triphenylmethane C6H5–CH(C6H5)2

86.3G2.0

361.1G8.4

Derived from DfH0 in ref.

1986PED/NAY

Tetraphenylmethane C6H5–C(C6H5)3

77.5G3

324.3G12.6

Derived from DfH0 in ref.

1986PED/NAY

1,1,2,2-Tetraphenylethane Ph2CH–CHPh2

59.1G2

247.3G8.4

Derived from DfH0 in ref.

1990BEC/DOG

1,2,2,2-Tetraphenylethane PhCH2–CPh3

56.1G3.5

234.7G14.6

Derived from DfH0 in ref.

1990BEC/DOG

72.4

302.9

VLPP

1986ROB/STE

1-Methylnaphthalene CH3–naphth-1-yl

103.8G2.0

434.3G8.4

Derived from DfH0 in ref.

1988LIA/BAR

2-Methylnaphthalene CH3–naphth-2-yl

105.3G2.0

440.6G8.4

Derived from DfH0 in ref.

1986PED/NAY

1-Methylindene CH3

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References

BDEs of C–C Bonds

165

Cyclo-hexylbenzene cyclo-C6H11–C6H5

98.7G2.0

413.0G8.4

Derived from DfH0 in ref.

1986PED/NAY

Ethyl-1-naphthalene CH3–1-naphthymethyl

72.9G1.5

305.0G6.3

VLPP

1980MCM/TRE

Ethyl-9-anthracene CH3–9-anthracenyl methyl

67.6G1.5

282.8G6.3

VLPP

1980MCM/TRE

Ethyl-9-phenanthrene CH3–9-phenanthrenyl methyl

72.9G1.5

305.0G6.3

VLPP

1980MCM/TRE

ESR

(1) 2003ZHE/SAE

Phenalenyl p-dimer R–R R=

(1) 11.34G0.11 47.4G0.5 (2) 10

42

(2) 2005SMA/ROS

(3) 10.2

42.7

(3) 2006ZAI/ROS

9.5

39.8

ESR

2004SMA/ZAI

12.6

52.7

ESR

2006ZAI/ROS

14.5

60.7

Phenalenyl s-dimer

Phenalenyl, substituted p-dimer R–R

R=

Phenalenyl, substituted s-dimer R–R

R=

X

XZH CH3

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 4.3 (continued) C–C BDEs in Aromatic Hydrocarbons

The broken bonds (boldfaceZdissociated group) 9-Phenylfluorenyl dimer Ph

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

15.2

63.6

Absorption spectra

2004FRE/ALI

74.8

313

Derived

1997DOR/PUG

72.9

305

SPST

1995TSA/CUI

R=

Cyclo-hexene

Tetralin

4.4

Halogenated hydrocarbons

Table 4.4 C–C BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Difluoroethyne CFbCF

167G7

700G29

Derived from DfH0 in ref.

1996NIST

Fluoroethyne CFbCH

174G4

728G17

Derived from DfH0 in ref.

1996NIST

Tetrafluoroethylene CF2aCF2

(1) 76.3 (2) 79.1G3.8 (3) 68.7

319.2 331G16 287.4

(1) Pyrolysis (2) Derived (3) Derived from DfH0 in ref.

(1) 1968ZMB/UY (2) 1991PAU/SQU (3) 2002CRC

Chlorotrifluoroethele CF2aCFCl

84.7G4

354.4G16.7

Derived from DfH0 in ref.

1996NIST

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BDEs of C–C Bonds

167

Trifluoroethlene CF2aCFH

104G3

435G13

Derived from DfH0 in ref.

1996NIST

1,1-Difluoroethylene CF2aCH2

132G3

552G13

Derived from DfH0 in ref.

1996NIST

Fluoroethlene CH2aCFH

160G3

669G13

Derived from DfH0 in ref.

1996NIST

1,2-Dichloroethyne CClbCCl

162G4.5

678G19

Derived from DfH0 in ref.

1996NIST

Chloroethyne CClbCH

197.6G3.5

627G17

Derived from DfH0 in ref.

1996NIST

Tetrachloroethylene CCl2aCCl2

(1) 106.3G4.9 (2) 110.6

445G21 462.8

(1) Derived (2) Derived from DfH0 in ref.

(1) 1991PAU/SUQ (2) 1986PED/NAY

Trichloroethlene CCl2aCClH

136.6G3

571.4G13

Derived from DfH0 in ref.

1996NIST

1,1-Dichloroethlene CCl2aCH2

146.8G3

614.1G13

Derived from DfH0 in ref.

1996NIST

155.6G2.8 155.0G2.8

651.0G11.7 648.5G11.7

Derived from DfH0 in ref.

1996NIST

Chloroethlene CHClaCH2

164.3G3

687.4G13

Derived from DfH0 in ref.

1996NIST

Bromoethyne CBrbCH

200G15

837G63

Derived from DfH0 in ref.

1996NIST

1,2-Dichloroethlene (E)-CHClaCHCl (Z)-CHClaCHCl

(continued)

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Table 4.4 (continued) C–C BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Perfluoroethane CF3–CF3

(1) (2) (3) (4) (5)

Pentafluoroethane CF3–CHF2

kJ/mol 389.1G8.4 413.0G10.5 413.0G5.0 403.3G21.8 409.2G12.5

(1) (2) (3) (4) (5)

(1) 95.5G2

399.6G8.4

(2) 97.3G2.3

407.2G9.6

(1) Derived from DfH0 in ref. (2) Combined

(1) 89.3G3

373.6G12.5

(2) 88.0G3.7

368.1G15.5

1,1,1,2-Tetrafluoroethane CF3–CH2F

95G2

1,1,1-Trifluoro-2,2-2trichloroethane CF3–CCl3

Chloropentafluoroethane CF3–CClF2

93G2 98.7G2.5 98.7G1.2 96.4G5.2 97.8G3.0

Methods (reference in parentheses) Pyrolysis Kinetics Derived Review Review

References (1) (2) (3) (4) (5)

1965TSC 1967COO/WHI 1998RUS/MIC 2001LAZ/PRO 2005GIA

(1) 1975CHE/ROD (2) 2005YAN/HUA(b)

(1) Derived from DfH0 in ref. (2) Review

(1) 2002CRC

397.5G8.4

Derived from DfH0 in ref.

1975CHE/ROD

79.4G1.3

332.2G5.4

Derived from DfH0 in ref.

1975CHE/ROD

1-Bromo-1-chloro2,2,2-trifluoroethane CF3–CHBrCl

90.1G2

377.0G10.5

Derived from DfH0 in ref.

1996NIST

1-Bromo-2,2,2trifluoroethane CF3–CH2Br

95.5G2

399.6G8.4

Derived from DfH0 in ref.

2002CRC

1,1,1-Trifluoro2-iodoethane CF3–CH2I

97.6G2.5

408.4G10.5

Derived from DfH0 in ref.

2002CRC

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(2) 2005GIA

BDEs of C–C Bonds 1,1,1-Trifluoroethane CF3–CH3

169 (1) 101.2G1.1 (2) 102.6G1.2

423.4G4.6 429.3G5.0

(1) 1973ROD/FOR (2) 1996NIST

423.9G8.6

(1) Kinetics (2) Derived from DfH0 in ref. (3) Review

(3) 101.3G2.1

1,1,2,2-Tetrafluoroethane CHF2–CHF2

(1) 91.4G3.7 (2) 95.7G3.7

382.4G15.5 400.3G15.5

(1) SPST (2) Review

(1) 1971MIL/HAR (2) 2005GIA

1,1,2-Trifluorochloroethane CHF2–CHFCl

93.0G4.2

389.0G17.5

Review

2005GIA

1,2-Dichlorotetrafluoroethane CClF2–CClF2

90.5G3

378.7G12.6

Derived from DfH0 in ref.

2002CRC

1,1,2-Trichloro-1,2,2trifluoroethane CF2Cl–CFCl2

85.7G3

358.6G12.6

Derived from DfH0 in ref.

1996NIST

1,1,2-Trifluoroethane CHF2–CH2F

(1) 94.2G4

394.1G16.7

(1) 1968LAC/SKI

(2) 98.0G3.7

410.1G15.6

(1) Derived from DfH0 in ref. (2) Review

(1) 88G2

368.2G8.4

(1) 1971KER/TIM

(2) 88.1G4.0

368.7G16.7

(1) Thermal elimination (2) Review

1,1-Difluoroethane CHF2–CH3

96.8G2

405.0G8.4

Derived from DfH0 in ref.

2002CRC

Fluoroethane CH2F–CH3

(1) 90.4G3

378.2G12.6

Derived from DfH0 in ref.

(1) 1975CHE/ROD

(2) 92.8G2

388.3G8.4

1,2-Difluoroethane CH2F–CH2F

(3) 2005GIA

(2) 2005GIA

(2) 2005GIA

(2) 2004KOR/LIE

(continued)

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Table 4.4 (continued) C–C BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 95.5G3

399.6G12.6

(2) 96.3G2.3

402.8G9.8

1-Bromo-2-chloro-1,1,2trifluoroethane CF2Br–CHClF

88.3

1-Bromo-1,1difluoroethane CF2Br–CH3

Methods (reference in parentheses)

References

(1) Derived from DfH0 in ref. (2) Review

(1) 2002CRC

369.4

Derived from DfH0 in ref.

1996NIST

94.8G3.6

396.6G15.1

Derived from DfH0 in ref.

1996NIST

Perchloroethane CCl3–CCl3

(1) 70.1G3.5 (2) 68.3G1.5

293.3G14.6 285.8G6.3

(1) Derived (2) Derived from DfH0 in ref.

(1) 1997CIO/LIU (2) 2002CRC

1,1,1,2-Tetrachloro2,2-difluoroethane CCl3–CClF2

67.4G3

282.0G12.6

Derived from DfH0 in ref.

2002CRC

Pentachloroethane CCl3–CHCl2

(1) 75.4G3.9 (2) 72.5G2

315.5G16.3 303.3G6.5

(1) Derived (2) Derived from DfH0 in ref.

(1) 1997CIO/LIU (2) 1996NIST

1,1,1,2-Tetrachloroethane (1) 77.4G2 CCl3–CH2Cl (2) 82.3G3.0

323.8G8.4

(1) Derived from DfH0 in ref. (2) Derived

(1) 1996NIST

(1) 87.6G2.0 (2) 86.6G1.5

366.5G8.4 362.3G6.3

(1) Derived (2) Derived from DfH0 in ref.

(1) 1997CIO/LIU (2) 2002CRC

1-Chloro-1-fluoroethane CHClF–CH3

1,1,1-Trichloroethane CCl3–CH3

344.3G12.6

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(2) 2005GIA

(2) 1997CIO/LIU

BDEs of C–C Bonds

171

1,1,2,2-Tetrachloroethane (1) 81.8G2 CHCl2–CHCl2 (2) 84.0G4.7 (3) 78.1G1.0

342.3G8.4

(1) Derived from DfH0 in ref. (2) Derived (3) Derived

(1) 1996NIST

(1) 84.2G1.4

352.2G5.9

(1) Derived from DfH0 in ref. (2) Derived

(1) 1996NIST

(2) 86.5G4.0

361.9G16.7

1,1-Dichloroethane CHCl2–CH3

(1) 89.8G3.3 (2) 87.3G0.8 (3) 86.4G0.6

375.7G13.8 365.1G3.3 361.3G2.5

(1) Derived (2) Derived (3) Derived from DfH0 in ref.

(1) 1997CIO/LIU (2) 1998SEE (3) 1996NIST

1,1-Bromochloroethane CHBrCl–CH3

88.6

370.7

Derived from DfH0 in ref.

1996NIST

1,2-Dibromo-1,2dichloroethane CHClBr–CHClBr

75.8G3

317.1G12.6

Derived from DfH0 in ref.

1996NIST

1,2-Dichloroethane CH2Cl–CH2Cl

(1) 87.2G3.3 (2) 86.2G2

364.8G13.8 360.7G8.4

(1) 1997CIO/LIU (2) 2002CRC

(3) 87.1G1.3

364.6G5.3

(1) Derived (2) Derived from DfH0 in ref. (3) Derived

Chloroethane CH2Cl–CH3

89.8G2.2

375.7G9.2

Derived

1997CIO/LIU

1,1,1-Tribromoethane Br3C–CH3

85.3G3

356.9G12.6

Derived from DfH0 in ref.

1996NIST

Hexabromoethane Br3C–CBr3

66.6G4

278.7G16.7

Derived from DfH0 in ref.

1996NIST

1,1-Dibromoethane CHBr2–CH3

89.1

372.8

Derived from DfH0 in ref.

1988LIA/BAR

1,1,2-Trichloroethane CHCl2–CH2Cl

351.5G19.7 326.9G4.1

(2) 1997CIO/LIU (3) 2006LAG/BAE(b)

(2) 1997CIO/LIU

(3) 2002LAG/DIO

(continued)

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Table 4.4 (continued) C–C BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1-Bromo-2-chloroethane CH2Br–CH2Cl

90.4

378.2

Derived from DfH0 in ref.

1988LIA/BAR

1,2-Dibromoethane CH2Br–CH2Br

90.8G2

379.9G8.4

Derived from DfH0 in ref.

1986PED/NAY

1,2-Diiodoethane CH2I–CH2I

92.5G2.5

387.0G10.5

Derived from DfH0 in ref.

1994CAR/LAY

Bromoethane CH3–CH2Br

91.2G2

381.6G8.4

Derived from DfH0 in ref.

1986PED/NAY

Iodoethane CH3–CH2I

91.9G2

384.5G8.4

Derived from DfH0 in ref.

1986PED/NAY

Perfluoropropane CF3–CF2CF3

(1) 101.9G2.4 (2) 101.4G3

426.3G10 424.3G13.6

Derived from DfH0 in ref.

(1) 1988NIST (2) 2002CRC

3,3,3-Trifluoroprop1-yne CF3–CbCH

123.2

515.5

Derived from DfH0 in ref.

1988LIA/BAR

3,3,3-Trifluoropropene CF3–CHaCH2

107G3

447.7G12.6

Derived from DfH0 in ref.

2002CRC

Perfluoropronpene CF3–CFaCF2

(1) 85G2.5 (2) 100.5

355.6G10.5 420.5

(1) SPST (2) Derived from DfH0 in ref.

(1) 1995HE (2) 2000CUI/HE

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BDEs of C–C Bonds

173

3,3-Dichloro-1,1,1trifluoropropane CF3–CH2CHCl2

102.3G1.5

428.0G6.3

Derived from DfH0 in ref.

1988NIST

Fluoropropane CH3–CH2CH2F

91.6G3

383.3G12.6

Derived from DfH0 in ref.

1998SMI

Fluoropropane CH2F–CH2CH3

101.5G3

424.7G12.6

Derived from DfH0 in ref.

1998SMI

2-Fluoropropane CH3–CHFCH3

93.7G2.5

392.0G10.5

Derived from DfH0 in ref.

2004KOR/LIE

1-Chloropropane CH3–CH2CH2Cl

88.8G0.6

371.4G2.8

Derived

1998SEE

2-Chloropropane CH3–CHClCH3

87.8G0.5

367.5G2.0

Derived

1998SEE

1,2-Dichloropropane CH2Cl–CHClCH3

85.2G2

356.5G8.4

Derived from DfH0 in ref.

2002CRC

1,3-Dichloropropane CH2Cl–CH2CClH2

88.2G2

369.0G8.4

Derived from DfH0 in ref.

2002CRC

2,2-Dichlororopane CH3–CCl2CH3

86.7G2

362.8G8.4

Derived from DfH0 in ref.

2002CRC

1,2-Dibromopropane CH2Br–CHBrCH3

88.3G2

369.4G8.4

Derived from DfH0 in ref.

2002CRC

1,3-Dichlorobutane CH2ClCH2–CHClCH3

87.1G2

364.4G8.4

Derived from DfH0 in ref.

2002CRC

(continued)

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Table 4.4 (continued) C–C BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1,4-Dichlorobutane CH2ClCH2– CH2CClH2

88.2G2

369.0G8.4

Derived from DfH0 in ref.

2002CRC

2,3-Dibromobutane CH3CHBr– CHBrCH3

85.0G2

355.6G8.4

Derived from DfH0 in ref.

2002CRC

1-Bromobutane CH2Br–C3H7

90.3G2

377.8G8.4

Derived from DfH0 in ref.

2002CRC

2-Bromobutane CH3CHBr–C2H5

87.5G2

366.1G8.4

Derived from DfH0 in ref.

2002CRC

4-Chlorobutene CH2Cl–CH2CHCH2

75.8G1.2

317.1G5

Derived from DfH0 in ref.

1996NIST

1-Chlorobutane CH2Cl–C3H7

88.7G2

371.1G8.4

Derived from DfH0 in ref.

2002CRC

2-Chlorobutane CH3CHCl–C2H5

85.2G2

356.5G8.4

Derived from DfH0 in ref.

2002CRC

1,4-Dibromobutane BrCH2CH2– CH2CH2Br

85.2G3

356.3G12.6

Derived from DfH0 in ref.

1996NIST

Erythro-2,3dibromobutane CH3CHBr–CHBrCH3

85.2G3

356.5G12.6

Derived from DfH0 in ref.

1996NIST

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BDEs of C–C Bonds

175

Threo-2,3-dibromobutane 84.9G3 CH3CHBr–CHBrCH3

355.2G12.6

Derived from DfH0 in ref.

1996NIST

2,2-Dibromobutane CH3CBr2–CH2CH3

83.8G2

350.6G8.4

Derived from DfH0 in ref.

1996NIST

1-Chlorobutane CH2Cl–iC3H7

87.1G2

364.4G8.4

Derived from DfH0 in ref.

2002CRC

1-Bromopentane CH2Br–nC4H9

90.3G2

377.8G8.4

Derived from DfH0 in ref.

2002CRC

1-Chloropentane CH2Cl–nC4H9

88.4G2

369.9G8.4

Derived from DfH0 in ref.

2002CRC

1-Chloropentane CH2ClCH2–C3H7

87.8G2

367.4G8.4

Derived from DfH0 in ref.

2002CRC

1,2-Dichlorobutane CH2ClCH2– CHClCH2CH3

81.4G3

340.6G12.6

Derived from DfH0 in ref.

1996NIST

2-Chloro-3methyl-butane CH2Cl–iso-C4H9

87.6G2

366.5G8.4

Derived from DfH0 in ref.

2002CRC

2-Chloro-3methyl-butane CH2ClCH2–iso-C3H7

86.1G2

360.2G8.4

Derived from DfH0 in ref.

2002CRC

1-Bromohexane CH2Cl–nC5H11

88.8G2

371.5G8.4

Derived from DfH0 in ref.

2002CRC

2-Chlorohexane CH2ClCH2–nC4H9

85.7G2

358.6G8.4

Derived from DfH0 in ref.

2002CRC

(continued)

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Table 4.4 (continued) C–C BDEs in Halogenated Hydrocarbons

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Perfluorobutane C2F3–C2F5

90.9G2.6

380.3G10.8

Review

2005GIA

Fluorononane CH2FCH2–nC7H13

90.0G3

376.6G12.6

Derived from DfH0 in ref.

1997SCH/VER

2,2-Difluorononane CH3CF2–nC7H13

91.2G3

381.6G12.6

Derived from DfH0 in ref.

1997SCH/VER

(chloromethyl)benzene CH2Cl–C6H5

102.7

429.7

Derived from DfH0 in ref.

2002VER/KRA

(bromomethyl)benzene CH2Br–C6H5

100.8

421.7

Derived from DfH0 in ref.

2002VER/KRA

(iodomethyl)benzene CH2I–C6H5

103.4

432.6

Derived from DfH0 in ref.

2002VER/KRA

(trifluoromethyl)benzene CF3–C6H5

110.7G3

463.2G12.6

Derived from DfH0 in ref.

1994PED

(trichloromethyl)benzene CCl3–C6H5

92.9G2

388.7G8.4

Derived from DfH0 in ref.

1996NIST

Pentafluorophenylmethane CH3–C6F5

105

439.3

Derived

1975CHO/GOL

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BDEs of C–C Bonds

177

Pentafluorophenyl trifluoromethane CF3–C6F5

104

435.1

Derived

1975CHO/GOL

(2,2,2-trifluoroethyl)benzene CF3–CH2C6H5

87.4G3

365.7G12.6

Derived from DfH0 in ref.

1997SCH/VER

(3,3-difluoropropyl)benzene CHF2–CH2CH2C6H5

97.8G4

409.2G16.7

Derived from DfH0 in ref.

1997SCH/VER

(3,3-difluoropropyl)benzene CHF2CH2–CH2C6H5

80.4G3

336.4G14.5

Derived from DfH0 in ref.

1997SCH/VER

Bipentafluorophenyl C6F5–C6F5

116.7

488.3

Combustion

1979PRI/SAP

(2,2,2-trifluoro-1-phenylethyl)benzene CF3–CHPh2

84.2G4

352.3G16.7

Derived from DfH0 in ref.

1997SCH/VER

(2,2,2-trifluoro-1,1diphenyl-ethyl)benzene CF3–CPh3

69.5G4

290.8G16.7

Derived from DfH0 in ref.

1997SCH/VER

1,1,2,3,4,4-Hexafluoro1,3-butadiene CF2CF–CFCF2

133.4G3

558.1G12.6

Derived from DfH0 in ref.

1996NIST

(3-fluoro-1,1-diphenylpropyl)benzene CH2FCH2–CPh3

65.7G4

274.9G16.7

Derived from DfH0 in ref.

1997SCH/VER

(continued)

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178

Comprehensive Handbook of Chemical Bond Energies

Table 4.4 (continued) C–C BDEs in Halogenated Hydrocarbons BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated group) (3,3-difluoro-1,1diphenylpropyl)benzene CHF2CH2–CPh3

kcal/mol 63.1G4

kJ/mol 264.0G16.7

Methods (reference in parentheses) Derived from DfH0 in ref.

4.5

Organic compounds containing heteroatoms

4.5.1

Organic compounds containing oxygen atoms

References 1997SCH/VER

Table 4.5.1 C–C BDEs in Organic Compounds Containing Oxygen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ethanol CH3–CH2OH

87.2G1.0

364.8G4.2

Derived from DfH0 in ref.

1986PED/NAY

2,2,2-Trifluoroethanol CF3–CH2OH

96.9G1.5

405.4G6.3

Derived from DfH0 in ref.

2002CRC

3,3,3-Trifluoro-1-propanol CF3–CH2CH2OH

97.8

409.2

Derived from DfH0 in ref.

1996NIST

Allyl alcohol C2H3–CH2OH

97.1G1.2

406.3G5.0

Derived from DfH0 in ref.

1996NIST

1-Propanol C2H5–CH2OH

85.3G1.2

356.9G5.0

Derived from DfH0 in ref.

1986PED/NAY

2,2,3,3-Tetrafluoro1-propanol CHF2CF2–CH2OH

90.7G2

379.5G8.4

Derived from DfH0 in ref.

2002CRC

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BDEs of C–C Bonds

179

1-Butanol C3H7–CH2OH

85.4G0.8

357.3G3.3

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-1-propanol iso-C3H7–CH2OH

84.8G1.0

354.8G4.2

Derived from DfH0 in ref.

1986PED/NAY

3-Buten-1-ol CH2CHCH2–CH2OH

72.0G1.2

301.3G5.0

Derived from DfH0 in ref.

2005VEL/QUI

3-Butyn-1-ol CHCCH2–CH2OH

73.0G1.2

305.3G5.0

Derived from DfH0 in ref.

2005VEL/QUI

1-Pentanol C4H9–CH2OH

85.0G1.0

355.6G4.2

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-1-butanol sec-C4H9–CH2OH

84.3G1.0

352.7G4.2

Derived from DfH0 in ref.

1986PED/NAY

3-Methyl-1-butanol iso-C4H9–CH2OH

84.6G1.3

354.0G5.4

Derived from DfH0 in ref.

1986PED/NAY

1-Hexanol nC5H11–CH2OH

84.4G1.3

353.1G5.4

Derived from DfH0 in ref.

1986PED/NAY

1-Heptanol nC6H13–CH2OH

85.1G1.0

356.2G4.2

Derived from DfH0 in ref.

1996NIST

Benzyl alcohol C6H5–CH2OH

96.1G0.9

401.9G3.9

Derived from DfH0 in ref.

2004VER/TAT

2-Propanol CH3–CH(CH3)OH

87.9G1.2

367.8G5.0

Derived from DfH0 in ref.

1986PED/NAY

2-Butanol C2H5–CH(CH3)OH

86.0G1.2

359.8G5.0

Derived from DfH0 in ref.

1986PED/NAY (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 4.5.1 (continued) C–C BDEs in Organic Compounds Containing Oxygen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

2-Pentanol C3H7–CH(CH3)OH

86.1G1.2

360.2G5.0

Derived from DfH0 in ref.

1986PED/NAY

3-Methyl-2-butanol iso-C3H7–CH(CH3)OH

83.9G1.3

351.0G5.4

Derived from DfH0 in ref.

1986PED/NAY

tert-Butyl alcohol CH3–C(CH3)2OH

83.5G1.2

349.4G5.0

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-2-butanol C2H5–C(CH3)2OH

81.2G1.2

339.7G5.0

Derived from DfH0 in ref.

1986PED/NAY

3-Pentanol C2H5–CH(C2H5)OH

84.8G1.2

354.8G5.0

Derived from DfH0 in ref.

1986PED/NAY

Ethylene glycol HOH2C–CH2OH

85.6G1.5

358.2G6.3

Derived from DfH0 in ref.

2002CRC

1,2-Propylene glycol CH3CH(OH)–CH2OH

86.2G1.8

360.7G7.5

Derived from DfH0 in ref.

2002CRC

1,2-Propanediol HOCH2–CH(CH3)OH

85.3G1.5

357.0G6.3

Derived from DfH0 in ref.

1996NIST

2,3-Butanediol OH(CH3)CH–CH(CH3)OH

90.5G1.5

378.7G6.3

Derived from DfH0 in ref.

1986PED/NAY

2-Aminoethan-1-ol NH2CH2–CH2OH

80.2G2.5

335.6G10.5

Derived from DfH0 in ref.

1988LIA/BAR

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BDEs of C–C Bonds

181

Ethyl methyl ether CH3–CH2OCH3

86.8G1.2

363.2G5.0

Derived from DfH0 in ref.

1986PED/NAY

Ethyl propyl ether C2H5–CH2OCH3

85.3G1.2

356.9G5.0

Derived from DfH0 in ref.

1986PED/NAY

1,2-Methyloxyethane CH3OCH2–CH2OCH3

(1) 81G2.5

338.9G10.5

(1) 1988LIA/BAR

(2) 68.7

287.5

(1) Der. from DfH0 in ref. (2) UV PI

(2) 2003WAN/WU

75G2

313.8G8.4

VLPP

1981STE

83.1

347.7

EPR

2001LUC/PED

Ketenylidene C–C(O)

52.8G4.6

220.9G19.3

Derived

1996ZEN/PER

Ethanal H2CaC(O)

78.73G0.02

329.41G0.08

GPA, revised

1999RUS/LIT

Acetaldehyde CH3–C(O)H

84.8G0.4

354.8G1.7

Derived from DfH0 in ref.

1986PED/NAY

Trichloroacetaldehyde CCl3–C(O)H

73.9G1.2

309.2G5.0

Derived from DfH0 in ref.

2002CRC

Acetyl fluoride CH3–C(O)F

103.0G2.2

430.8G6.3

Derived from DfH0 in ref.

1996NIST

Acetyl chloride CH3–C(O)Cl

87.9G1.5

367.8G6.3

Derived from DfH0 in ref.

2002CRC

2-Ethyl furan O CH 3

6-(tert-butyl)-2-(3-(tert-butyl)-2hydroxyphenyl)phenyl OH

OH

Me3C

CMe3

(continued)

7366—CHAPTER 4—5/2/2007—20:04—BSARAVANAN—15360—XML MODEL B – pp. 147–210

182

Comprehensive Handbook of Chemical Bond Energies

Table 4.5.1 (continued) C–C BDEs in Organic Compounds Containing Oxygen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Trichloroacetyl chloride CCl3–C(O)Cl

69.1G1.5

289.1G6.3

Derived from DfH0 in ref.

2002CRC

Dichloroacetyl chloride CHCl2–C(O)Cl

74.7G2

312.5G8.4

Derived from DfH0 in ref.

2002CRC

Chloroacetyl chloride CClH2–C(O)Cl

81.3G2

340.2G8.4

Derived from DfH0 in ref.

2002CRC

Propanoyl chloride C2H5–C(O)Cl

86.2G1.2

360.7G5.0

Derived from DfH0 in ref.

1998WIN/ROW

Propanal C2H5–C(O)H

82.7G0.5

346.0G2.1

Derived from DfH0 in ref.

1986PED/NAY

(Z)-2-Butenal CH3CHaCH–C(O)H

97.8G2.0

409.2G8.4

Derived from DfH0 in ref.

1986PED/NAY

Butanal C3H7–C(O)H

82.7G1.0

346.0G4.2

Derived from DfH0 in ref.

1986PED/NAY

2-Methylpropanal iso-C3H7–C(O)H

82.5G1.2

345.2G5.0

Derived from DfH0 in ref.

1986PED/NAY

Pentanal nC4H9–C(O)H

83.2G0.7

348.1G2.9

Derived from DfH0 in ref.

1986PED/NAY

Heptanal nC6H13–C(O)H

81G2.0

338.9G8.4

Derived from DfH0 in ref.

1994PED

7366—CHAPTER 4—5/2/2007—20:04—BSARAVANAN—15360—XML MODEL B – pp. 147–210

BDEs of C–C Bonds

183

Benzaldehyde C6H5–C(O)H

97.6G1.0

408.4G4.2

Derived from DfH0 in ref.

1986PED/NAY

Benzonyl chloride C6H5–C(O)Cl

99.8G1.5

417.6G6.3

Derived from DfH0 in ref.

1996NIST

Propanal CH3–CH2C(O)H

82.0G2.4

343.1G10.0

Derived from DfH0 in ref.

1986PED/NAY

Propanal chloride CH3–CH2C(O)Cl

85.5G3.3

357.7G13.8

Derived from DfH0 in ref.

1998WIN/ROW

2-Propen-1-ol C2H3–CH2C(O)H

97.1G2

406.1G8.4

Derived from DfH0 in ref.

1996NIST

Butanal C2H5–CH2C(O)H

79.8G2.5

333.9G10.5

Derived from DfH0 in ref.

1986PED/NAY

Pentanal C3H7–CH2C(O)H

80.9G2.5

338.5G10.5

Derived from DfH0 in ref.

1986PED/NAY

Heptanal C5H11–CH2C(O)H

78.5G3.0

328.4G12.6

Derived from DfH0 in ref.

1986PED/NAY

3-Phenylpropanone C6H5CH2–CH2C(O)H

69.2G1.5

289.5G6.3

Derived from DfH0 in ref.

1988LIA/BAR

Dimethyl ketone CH3–C(O)CH3

84.1G0.5

351.9G2.1

Derived from DfH0 in ref.

1986PED/NAY

Bromoacetone CH2Br–C(O)CH3

85.9G1.5

359.4G6.3

Derived from DfH0 in ref.

2002CRC (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 4.5.1 (continued) C–C BDEs in Organic Compounds Containing Oxygen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Chloroacetone CH2I–C(O)CH3

83.5G2.5

349.4G10.5

Derived from DfH0 in ref.

1986PED/NAY

Ethyl methyl ketone CH3–C(O)C2H5

84.6G0.8

354.1G3.5

Derived

2005KER/FOG

Ethyl methyl ketone C2H5–C(O)CH3

83.0G0.7

347.3G2.9

Derived from DfH0 in ref.

1986PED/NAY

Methyl vinyl ketone CH3–C(O)C2H3

81.8G3

342.3G12.6

Derived from DfH0 in ref.

1996NIST

Methyl vinyl ketone C2H3–C(O)CH3

96.6G3

404.2G12.6

Derived from DfH0 in ref.

1996NIST

Diethyl ketone C2H5–C(O)C2H5

81.4G0.8

340.7G3.5

Derived

2005KER/FOG

Methyl propyl ketone C3H7–C(O)CH3

83.3G0.7

348.5G2.9

Derived from DfH0 in ref.

1986PED/NAY

Ethyl propyl ketone C3H7–C(O)C2H5

82.3G1.3

344.3G5.4

Derived from DfH0 in ref.

1994PED

iso-Propyl methyl ketone iso-C3H7–C(O)CH3

81.3G0.9

340.2G3.8

Derived from DfH0 in ref.

1986PED/NAY

iso-Propyl ethyl ketone iso-C3H7–C(O)C2H5

81.6G1.5

341.4G6.3

Derived from DfH0 in ref.

1994PED

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BDEs of C–C Bonds

185

Butyl methyl ketone nC4H7–C(O)CH3

82.9G1.3

346.9G5.4

Derived from DfH0 in ref.

1986PED/NAY

tert-Butyl methyl ketone tert-C4H9–C(O)CH3

78.7G1.0

329.3G4.2

Derived from DfH0 in ref.

1986PED/NAY

Phenyl methyl ketone C6H5–C(O)CH3

97.2G1.1

406.7G4.6

Derived from DfH0 in ref.

1996NIST

tert-Butyl ethyl ketone tert-C4H9–C(O)C2H5

78.8G1.0

329.7G4.2

Derived from DfH0 in ref.

1994PED

Benzyl methyl ketone C6H5CH2–C(O)CH3

71.4G2

299.7G8.4

Derived from DfH0 in ref.

1994PED

Benzyl phenyl ketone C6H5CH2–C(O)C6H5

72.5G3

303.3G12.6

Derived from DfH0 in ref.

1986PED/NAY

Ethyl methyl ketone CH3–CH2C(O)CH3

86.5G3

361.9G12.6

Derived from DfH0 in ref.

1986PED/NAY

Butyl methyl ketone C3H7–CH2C(O)CH3

82.4G1.5

344.8G6.3

Derived from DfH0 in ref.

2002CRC

Methyl phenyl ketone CH3–C(O)C6H5

85.0

355.6

Photolysis

1997ZHA/CHE

Trifluoromethyl phenyl ketone CF3–C(O)C6H5

73.8G2

308.8G8.4

VLPP

1977COL/ZAB

Ethyl phenyl ketone C2H5–C(O)C6H5

82.2G2.8

343.9G11.7

Derived from DfH0 in ref.

1986PED/NAY (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 4.5.1 (continued) C–C BDEs in Organic Compounds Containing Oxygen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Diphenyl ketone C6H5–C(O)C6H5

94.7G4

396.2G16.7

Derived from DfH0 in ref.

1988LIA/BAR

Benzyl phenyl ketone PhCH2–C(O)Ph

72.5G3.5

303.3G14.6

Derived from DfH0 in ref.

1986PED/NAY

Bibenzyl ketone PhCH2–C(O)CH2Ph

65.4

273.6

Review

1982MCM/GOL

Ethane-1,2-dial HC(O)–C(O)H

70.7G1.5

295.8G6.3

Derived from DfH0 in ref.

1996NIST

Oxalyl chloride ClC(O)–C(O)Cl

69.9G2

292.5G8.4

Derived from DfH0 in ref.

1996NIST

1,2-Propanedione CH3C(O)–C(O)H

72.3G2

302.5G8.4

Derived from DfH0 in ref.

2002CRC

Biacetyl CH3C(O)–C(O)CH3

73.4G1

307.1G4.2

Derived from DfH0 in ref.

1986PED/NAY

Pentane-2,3-dione C2H5C(O)–C(O)CH3

72.2G1.1

302.2G4.5

Derived

2005KER/FOG

Bibenzoyl C6H5C(O)–C(O)C6H5

68.9G4

288.3G16.7

Review

1982MCM/GOL

2,4-Pentanedione CH3C(O)–CH2C(O)CH3

80.8G2

338.1G8.4

Derived from DfH0 in ref.

1994PED

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BDEs of C–C Bonds

187

Acetic acid CH3–C(O)OH

92.0G2

384.9G8.4

Derived from DfH0 in ref.

1986PED/NAY

Trifluoroacetic acid CF3–C(O)OH

88.6G2

370.7G8.4

Derived from DfH0 in ref.

2002CRC

Trichloroacetic acid CCl3–C(O)OH

74.2G3

310.5G12.6

Derived from DfH0 in ref.

1996NIST

Chloroacetic acid CClH2–C(O)OH

85.5G2

357.7G8.4

Derived from DfH0 in ref.

2002CRC

Bromoacetic acid CH2Br–C(O)OH

85.6G2

358.2G8.4

Derived from DfH0 in ref.

2001DOR/NOV

Glycine NH2CH2–C(O)OH

83.5G2

349.4G8.4

Derived from DfH0 in ref.

2002CRC

N-methylglycine CH3NHCH2–C(O)OH

71.8G2

300.4G8.4

Derived from DfH0 in ref.

2002CRC

Propenoic acid C2H3–C(O)OH

(1) 104.1G2

435.6G8.4

(1) 1996NIST

(2) w100

w418

(1) Der. from DfH0 in ref. (2) PD

Propanoic acid C2H5–C(O)OH

90.8G1.5

379.9G6.3

Derived from DfH0 in ref.

1986PED/NAY

2-Chloropropanoinc acid CH3CHCl–C(O)OH

85.5G2

357.7G8.4

Derived from DfH0 in ref.

2002CRC

Butanoic acid C3H7–C(O)OH

91.0G1.5

380.7G6.3

Derived from DfH0 in ref.

1986PED/NAY

(2) 1997KIT/FOR

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 4.5.1 (continued) C–C BDEs in Organic Compounds Containing Oxygen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pentanoic acid C4H9–C(O)OH

89.7G1.5

375.3G6.3

Derived from DfH0 in ref.

1994PED

3-Methylbutanoic acid sec-C4H9–C(O)OH

91.6G3

383.3G12.6

Derived from DfH0 in ref.

1986PED/NAY

2,2-Dimethylpropanoic acid 82.5G4 tert-C4H9–C(O)OH

345.2G16.7

Derived from DfH0 in ref.

1986PED/NAY

Hexanoic acid C5H11–C(O)OH

88.8G1.5

371.5G6.3

Derived from DfH0 in ref.

1994PED

Heptanoic acid C6H13–C(O)OH

89.7G1.5

375.3G6.3

Derived from DfH0 in ref.

1994PED

Benzoic acid Ph–C(O)OH

102.7G2

429.7G8.4

Derived from DfH0 in ref.

1994PED

Pentafluoro-benznic acid C6F5–C(O)OH

97.1G2.5

406.1G10.5

Derived from DfH0 in ref.

1996NIST

2-Phenylacetic acid PhCH2–C(O)OH

67

280.3

Review

1970ONE/BEN

Diphenylacetic acid Ph2CH–C(O)OH

59.4G3

248.5G12.6

Review

1970ONE/BEN

Naphthlene-1-carboxylic acid C10H7–1-C(O)OH

102.8G2.0

430.1G8.4

Derived from DfH0 in ref.

1986PED/NAY

7366—CHAPTER 4—5/2/2007—20:04—BSARAVANAN—15360—XML MODEL B – pp. 147–210

BDEs of C–C Bonds

189

Naphthlene-2-carboxylic acid C10H7–2-C(O)OH

104.8G2.0

438.5G8.4

Derived from DfH0 in ref.

1986PED/NAY

Glycolic acid HOCH2–C(O)OH

88.8G1.3

371.5G5.4

Derived from DfH0 in ref.

2001DOR/NOV

Oxalic acid HOC(O)–C(O)OH

80.0G1.5

334.7G6.3

Derived from DfH0 in ref.

1994PED

Sarcosine CH3NHCH2–C(O)OH

72.0G4

301.2G16.7

Derived from DfH0 in ref.

1988LIA/BAR

L-alanine

79.2G4

331.4G16.7

Derived from DfH0 in ref.

1988LIA/BAR

Acetic acid methyl ester CH3–C(O)OCH3

92.6G3

387.4G12.5

Derived from DfH0 in ref.

1986PED/NAY

Methyl-2,2,2trifluoroacetate CF3–C(O)OCH3

85.5G2.5

357.7G10.5

Derived from DfH0 in ref.

1996NIST

Chloroacetic acid methyl ester CH2Cl–C(O)OCH3

90.6G3.2

379.1G13.4

Derived from DfH0 in ref.

1996NIST

Methyl acrylate C2H3–C(O)OCH3

106.2G2.5

444.3G10.5

Derived from DfH0 in ref.

2002CRC

Pentafluoropropanoic acid methyl ester C2F5–C(O)OCH3

87.5G2.5

366.0G10.5

Derived from DfH0 in ref.

1996NIST

CH3CH(NH2)–C(O)OH

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 4.5.1 (continued) C–C BDEs in Organic Compounds Containing Oxygen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1-Chloro-ropropanoic acid methyl ester CH2ClCH2–C(O)OCH3

87.8G3

367.4G12.6

Derived from DfH0 in ref.

1996NIST

Methyl benzoate Ph–C(O)OCH3

(1) 102.8G3 (2) 104.4G2.5

430.1G12.6 436.8G10.5

Derived from DfH0 in ref.

(1) 1986PED/NAY (2) 2002ROU/TEM

Methyl-2-phenylpropionate C6H5CH(CH3)–C(O)OCH3

77.1G2.0

322.6G8.4

Derived from DfH0 in ref.

1999VER(b)

Methyl 2-hydroxyacetate HOCH2–C(O)OCH3

88.5G2.5

370.3G10.5

Derived from DfH0 in ref.

1996NIST

Dimethyl oxalate CH3OC(O)–C(O)OCH3

88.4G2.5

369.9G10.5

Derived from DfH0 in ref.

2002CRC

Propanoic acid CH3–CH2C(O)OH

84.5G3

353.5G12.6

Derived from DfH0 in ref.

2002CRC

Butanoic acid C2H5–CH2C(O)OH

82.6G3

345.6G12.6

Derived from DfH0 in ref.

1986PED/NAY

b-alanine NH2CH2–CH2C(O)OH

77.8G4

325.5G16.7

Derived from DfH0 in ref.

1988LIA/BAR

Butanedioic acid HO(O)CH2–CH2C(O)OH

81.9G1.0

342.7G4.3

Derived

2002LAG/DIO

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BDEs of C–C Bonds

191

Methyl ketene CH3–CHaCaO

93.3G1.5

390.4G6.3

Derived from DfH0 in ref.

2000TRA

Diketene OaCaCH–CHaCaO

129.9G2

543.5G8.4

Derived from DfH0 in ref.

2002CRC

2,3-Dimethylbutanedioic acid, R–R, R is CH(CH3)C(O)OH

66.7G1.6

279.1G6.7

Derived

2002LAG/DIO

2-Chlorooxirane O CH 2Cl

89.8G2.5

375.7G10.5

Derived from DfH0 in ref.

1986PED/NAY

2-Methyoxirane O CH3

93.5G2.5

391.2G10.5

Derived from DfH8 in ref.

1986PED/NAY

74.6G2.5

312.1G10.5

Derived from DfH0 in ref.

1988LIA/BAR

23.6

98.7

Absorption spectra

2004FRE/ALI

22.8

95.4

Proline NH

C(O)OH

Radical dimer

Ph

R=

O

O O

O

4.5.2

Organic compounds containing nitrogen atoms

Table 4.5.2 C–C BDEs in Organic Compounds Containing Nitrogen Atom(s)

The broken bonds (boldfaceZdissociated group) Cyanogen CN–CN

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

136.7G1.6

572.0G6.7

Methods (reference in parentheses) Derived from DfH0 in ref.

References 1986PED/NAY (continued)

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Table 4.5.2 (continued) C–C BDEs in Organic Compounds Containing Nitrogen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Formyl cyanide HC(O)–CN

108.8G2

455.2G8.4

Derived from DfH0 in ref.

1996BOR/ING

Thioformyl cyanide HC(S)–CN

126.7G2

530.1G8.4

Derived from DfH0 in ref.

1996BOR/ING

Trifluoroacetonitrile CF3–CN

(1) 112.1G1.0

469.0G4.2

(1) 1996NIST

(2) 112.6G1.3

471.1G5.4

(1) Der. from DfH0 in ref. (2) Derived

Acetonitrile CH3–CN

124.7G2.2

521.7G9.2

Derived from DfH0 in ref.

1986PED/NAY

Propiolonitrile CHbC–CN

(1) 143.9 (2) 155.5G2.5

(1) 602.1 (1) Photolysis (2) 650.6G10.5 (2) Der. from DfH0 in ref.

(1) 1973OKA/DIB (2) 1996NIST

2-Butynedinitrile NCC–CN

110.5

462.3

Derived from DfH0 in ref.

1996NIST

2-Propenenitrile CH2CH–CN

133.4G1.8

558.1G7.5

Derived from DfH0 in ref.

1986PED/NAY

Propanenitrile C2H5–CN

121.1G1.8

506.7G7.5

Derived from DfH0 in ref.

1986PED/NAY

2-Butenenitrile CH3CHCH–CN

131.0

548

Photoinozation

2000LI/KOV

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

(2) 1998RUS/MIC

BDEs of C–C Bonds

193

3-Butenenitrile CH2CHCH2–CN

108.1G2

452.3G8.4

Derived from DfH0 in ref.

1996NIST

2-Butenenitrile CH3CHCH–CN

135.2G2

565.7G8.4

Derived from DfH0 in ref.

1996NIST

Butanenitrile C3H7–CN

120.8G2.0

505.4G8.4

Derived from DfH0 in ref.

1986PED/NAY

2-Methylpropanenitrile iso-C3H7–CN

120.4G2.0

503.8G8.4

Derived from DfH0 in ref.

1986PED/NAY

Pentanenitrile nC4H9–CN

121.1G2.0

506.7G8.4

Derived from DfH0 in ref.

1986PED/NAY

2,2-Dimethylpropanenitrile tert-C4H9–CN

117.2G2.0

490.4G8.4

Derived from DfH0 in ref.

1986PED/NAY

Cyclo-butanecarbonitrile cyclo-C4H7–CN

122.2G2.0

511.3G8.4

Derived from DfH0 in ref.

1986PED/NAY

Cyclo-pentanecarbonitrile cyclo-C5H9–CN

120.0G2.0

502.1G8.4

Derived from DfH0 in ref.

1986PED/NAY

Cyclo-hexanecarbonitrile cyclo-C6H11–CN

121.9G2.0

510.0G8.4

Derived from DfH0 in ref.

1986PED/NAY

Benzonitrile C6H5–CN

132.3G2.0

553.5G8.4

Derived from DfH0 in ref.

1986PED/NAY

Heptanenitrile nC6H13–CN

120.4G2.0

503.8G8.4

Derived from DfH0 in ref.

1986PED/NAY (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 4.5.2 (continued) C–C BDEs in Organic Compounds Containing Nitrogen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Benzylcyanide C6H5CH2–CN

107.4G2

449.4G8.4

Derived from DfH0 in ref.

2000VER

a-Methyl-benzylcyanide C6H5CH(CH3)–CN

106.2G2.3

444.3G9.6

Derived from DfH0 in ref.

2000VER

a,a-Dimethylbenzylcyanide C6H5C(CH3)2–CN

102.8G2

430.1G8.4

Derived from DfH0 in ref.

2000VER

Propanenitrile CH3–CH2CN

83.2G3

348.1G12.6

Derived from DfH0 in ref.

1986PED/NAY

Butanenitrile C2H5–CH2CN

(1) 76.9G1.7 (2) 80.8G2

321.7G7.1 338.1G8.4

(1) VLPP (2) Der. from DfH0 in ref.

(1) 1975KIN/GOD (2) 1986PED/NAY

3-Butenenitrile C2H3–CH2CN

110.4G2

461.9G8.4

Derived from DfH0 in ref.

2002CRC

Pentanenitrile nC3H7–CH2CN

81.7G3

341.8G12.6

Derived from DfH0 in ref.

1986PED/NAY

2-Methylbutanenitrile iso-C3H7–CH2CN

73G2

305.4G8.4

VLPP

1975KIN/GOD

Heptanenitrile nC5H11–CH2CN

80.8G3

338.1G12.6

Derived from DfH0 in ref.

1986PED/NAY

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BDEs of C–C Bonds

195

Octanenitrile nC6H13–CH2CN

80.5G3

336.8G12.6

Derived from DfH0 in ref.

1986PED/NAY

Benzylcyanide C6H5–CH2CN

92.4G2

386.6G8.4

Derived from DfH0 in ref.

2000VER

2-Methylpropanenitrile CH3–CH(CH3)CN

(1) 78.8G2 (2) 79.5G2

329.7G8.4 332.6G8.4

(1) VLPP (2) Der. from DfH0 in ref.

(1) 1975KIN/GOD (2) 1986PED/NAY

a-methyl-benzylcyanide C6H5–CH(CH3)CN

92.7G2

387.7G8.4

Derived from DfH0 in ref.

2000VER

2,2-Dimethyl propanenitrile CH3–C(CH3)2CN

(1) 74.7G1.6 (2) 81.4G4

312.5G6.7 340.6G16.7

(1) VLPP (2) Der. from DfH0 in ref.

(1) 1976KIN/GOD (2) 1996NIST

a,a–Dimethylbenzylcyanide C6H5–C(CH3)2CN

90.6G4

379.1G16.7

Derived from DfH0 in ref.

2000VER

Propanedinitrile (CN)CH2–CN

101.9G3

426.3G12.6

Derived from DfH0 in ref.

1986PED/NAY

Butanedinitrile (CN)CH2–CH2CN

70.7G4

295.8G16.7

Derived from DfH0 in ref.

1986PED/NAY

Tetramethylbutanedinitrile 61.2G3 (CN)C(CH3)2–C(CH3)2CN

256.1G12.6

Derived from DfH0 in ref.

1986PED/NAY

2-Methy-2-phenylpropanenitrile CH3–C(CH3)(CN)C6H5

250.6

Pyrolysis

1982MEO

59.9

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 4.5.2 (continued) C–C BDEs in Organic Compounds Containing Nitrogen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

138.5

580

Derived from DfH0 in ref.

1996NIST

26.2

109.6

Adsorption spectra

2004FRE/ALI

(1) 97.9G2

409.6G8.4

(1) 1986PED/NAY

3-Me

(1) 103.2G2

431.8G8.4

(1) Der. from DfH0 in ref.

4-Me

(1) 103.7G2

433.9G8.4

2-CH2Ph

(2) 86.7

362.8

(2) VLPP

(2) 1984ROS/MCM

2-Et

(3) 95.9G3

401.2G12.6

(3) Der. from DfH0 in ref.

(3) 2005SIL/MIR

At 2 site

110.8G2.5

463.6G10.5

Derived from DfH0 in ref.

2000SIL/MAT

3 site

114.8G2.5

480.3G10.5

4 site

115.0G2.5

481.2G10.5

125.1G3.5

523.4G14.6

Derived from DfH0 in ref.

2000SIL/MIR

C(O)OH

98.1G3.5

410.5G14.6

C(O)NH2

98.1G3.5

410.5G14.6

2-Butynedinitrile NCCbCCN Diphenyl-CN-methyl dimer CN R= Ph Ph

Pyridine, substituted HO(O)C-pyridyl 3 2 1N R 5 6 4

RZ2-Me

Pyridine, substituted HO(O)C-pyridyl 3 2 1N R 5 6 4

Pyridines, substituted X N 4

2 3

XaCN

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

BDEs of C–C Bonds

197

2-Ethylpyridine CH3–2-pyridylmethyl

75.5G2.9

315.9G12.1

VLPP

1981BAR/STE

3-Ethylpyridine CH3–3-pyridylmethyl

73.9G2.6

309.2G10.9

VLPP

1981BAR/STE

4-Ethylpyridine CH3–4-pyridylmethyl

74.6G2.6

312.1G10.9

VLPP

1981BAR/STE

At 2 site

(1) 92.1G2.5

385.3G10.5

Derived from DfH0 in ref.

(1) 2005MAT/MOR

3 site

(1) 93.9G3.5 (2) 99.9

392.9G14.6 418

(1) 97.1G2.5

406.1G10.5

91.1G3

381.2G12.6

CN

117.5G3.5

491.6G14.6

C(O)OH

91.4G3.5

382.4G14.6

C(O)NH2

92.2G3.5

385.8G14.6

83.9G3

Pyridine, substituted HO(O)C-pyridyl 3 2 1N R 5 6 4

4 site

(2) 1996NIST

Pyrazines, substituted N N

X

XZC2H5

2-Methylpiperidine CH3 NH

Ethylamine CH3–CH2NH2

Derived from DfH0 in ref.

2005SIL/MIR

351.0G12.6

Derived from DfH0 in ref.

1986PED/NAY

(1) 82.7G2.3

346.0G9.6

(1) 1986PED/NAY

(2) 82.2

344.1

(1) Der. from DfH0 in ref. (2) Derived

(2) 2003MIR/KON (continued)

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

198

Comprehensive Handbook of Chemical Bond Energies

Table 4.5.2 (continued) C–C BDEs in Organic Compounds Containing Nitrogen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Propylamine C2H5–CH2NH2

81.5G2.3

341.0G9.6

Derived from DfH0 in ref.

1986PED/NAY

Phenylmethylamine C6H5–CH2NH2

94.2G2.5

394.1G10.5

Derived from DfH0 in ref.

1986PED/NAY

Benzyl dimethylamine C6H5–CH2N(CH3)2

92.7G2.5

387.9G10.5

Derived from DfH0 in ref.

1999VER

Benzyl methylamine C6H5CH2–CH2NH2

68.0G2

284.5G8.4

Pyrolysis

1977COL/BEN

2-Propylamine CH3–CH(CH3)NH2

83.1G2.3

347.7G9.6

Derived from DfH0 in ref.

1986PED/NAY

2-Methylpropylamine CH3–C(CH3)2NH2

73.4G2.5

307.1G10.5

Derived from DfH0 in ref.

1986PED/NAY

1,2-Ethanediamine NH2CH2–CH2NH2

(1) 68.4G3

286.2G12.6

(1) 1986PED/NAY

(2) 76.2

319.0

(1) Der. from DfH0 in ref. (2) Derived

1,2-Propanediamine NH2CH2–CH(CH3)NH2

75.8G3

317.1G12.6

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-1,2propanediamine NH2CH2–C(CH3)2NH2

74.6G3

312.1G12.6

Derived from DfH0 in ref.

1986PED/NAY

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

(2) 2003MIR/KON

BDEs of C–C Bonds

199

2-(2-pyridyl)pyridine NC5H4–C5H4N

103.9G3

434.7G12.6

Derived from DfH0 in ref.

1988LIA/BAR

Nitro[2-(nitroamino) ethyl]amine O2NCH2–CH2NO2

50.5

211.3

Derived

2003MIR/KON

Methoxyacetonitrile CH3OCH2–CN

113.5

474.9

Derived from DfH0 in ref.

1996NIST

Oxopropanedinitrile NCC(O)–CN

96.0G2.5

401.7G10.5

Derived from DfH0 in ref.

2001DOR/NOV

Nitroethane CH3–CH2NO2

(1) 94.7 (2) 87.1

369.2 364.4

(1) Derived (2) Der. from DfH0 in ref.

(1) 2000MAT/LEB (2) 2002CRC

1-(dimethylamino)-2propanone (CH3)2NCH2–C(O)CH3

73.8

308.8

Derived from DfH0 in ref.

1996NIST

Methyl ester nitrous acid H2NCH2–C(O)OH

83.1G2.5

347.7G10.5

Derived from DfH0 in ref.

1996NIST

Alanine H2NC(CH3)H–C(O)OH

79.3G3

331.8G12.6

Derived from DfH0 in ref.

1996NIST

Acetamide CH3–C(O)NH2

88.5G1.5

370.3G6.3

Derived from DfH0 in ref.

1996NIST

Propanamide C2H5–C(O)NH2

86.7G1.5

362.8G6.3

Derived from DfH0 in ref.

1996NIST (continued)

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

200

Comprehensive Handbook of Chemical Bond Energies

Table 4.5.2 (continued) C–C BDEs in Organic Compounds Containing Nitrogen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Benzamide C6H5–C(O)NH2

99.5G3

416.3G12.6

Derived from DfH0 in ref.

1996NIST

1-Nitropropane C2H5–CH2NO2

90.7

379.5

Derived

2000MIR/VOR(b)

1-Nitrobutane C3H7–CH2NO2

90.8

379.9

Derived

2000MIR/VOR(b)

1-Nitropentane C4H9–CH2NO2

89.5

374.5

Derived

2000MIR/VOR(b)

2-Nitropropane CH3–CH(NO2)CH3

90.0

376.6

Derived

2000MIR/VOR(b)

2-Nitrobutane CH3–CH(NO2)C2H5

90.3

377.8

Derived

2000MIR/VOR(b)

1,2-Dinitroethane NO2CH2–CH2NO2

93.8

392.5

Derived

2000MAT/LEB

1,1-Dinitroethane CH3–CH(NO2)2

99.3

415.5

Derived

2000MAT/LEB

1,1-Dinitropropane C2H5–CH(NO2)2

95.1

397.9

Derived

2000MIR/VOR(b)

2,2-Dinitropropane CH3–C(NO2)2CH3

92.2

385.8

Derived

2000MIR/VOR(b)

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

BDEs of C–C Bonds

201

1,1-Dinitrobutane C3H7–CH(NO2)2

95.8

400.8

Derived

2000MIR/VOR(b)

1,1-Dinitropentane C4H9–CH(NO2)2

94.6

395.8

Derived

2000MIR/VOR(b)

1,1,1-Trinitroethane H3C–C(NO2)3

98.3

411.3

Derived

2002MAT/LEB(a)

1,1,1-Trinitropropane H2C5–C(NO2)3

93.9

392.9

Derived

2000MIR/VOR(b)

1,1,1-Trinitrobutane H3C7–C(NO2)3

94.5

395.4

Derived

2000MIR/VOR(b)

1,1,1-Trinitropentane H4C9–C(NO2)3

93.5

391.2

Derived

2000MIR/VOR(b)

2,3-Dimethyl-2,3dinitrobutane (CH3)2C(NO2)– C(NO2)(CH3)2

72.7

304.2

Derived

2000MIR/VOR(b)

2,2,3,3-Tetranitrobutane 74.9 CH3C(NO2)2–C(NO2)2CH3

313.4

Derived

2000MIR/VOR(b)

Pentanitropropane CH3–C(NO2)C(NO2)3

72.6

303.8

Derived

2000MIR/VOR(b)

Hexanitrothane (NO2)3C–C(NO2)3

73.8

308.8

Derived

2000MAT/LEB

Trinitromethancyanide NC–C(NO2)3

101.6

425.1

Derived

2002MAT/LEB(a) (continued)

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

202

Comprehensive Handbook of Chemical Bond Energies

Table 4.5.2 (continued) C–C BDEs in Organic Compounds Containing Nitrogen Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Nitro(2-(nitrooxy)ethyl)oxy O2NOH2C–CH2ONO2

91.0

380.7

Derived

2002MAT/LEB(a)

Nitro(2-(nitrooxy) ethyl)amine O2NNHH2C– CH2NHNO2

68.2

285.3

Derived

2002MAT/LEB(a)

Nitrozoamines 74.0 (NO2)3C– CH2N(NO2)CH2C(NO2)3

309.6

Derived

2001MIR/KOS

(NO2)2CH–CH2N(NO2) CH2CH(NO2)2

79.5

332.6

(NO2)3CCH2–CH2N(NO2) 70.5 CH2C(NO2)3

295.0

(NO2)3C–H2CH2N(NO2) CH2C(NO2)3

87.3

365.3

(NO2)3CCH2N(NO2) CH2–CH2N(NO2) CH2C(NO2)3

56.3

235.6

(NO2)3C–CH2N(NO2) CH2CH2N(NO2) CH2C(NO2)3

74.5

311.7

(NO2)2CHCH2N(NO2) CH2–CH2N(NO2) CH2CH(NO2)2

61.6

257.7

(NO2)2CH–CH2N(NO2) CH2-CH2N(NO2) CH2CH(NO2)2

79.8

333.9

(NO2)3C– 73.8 CH2N(NO)CH2C(NO2)3

308.8

(NO2)3CCH2N(NO)CH2– 53.2 CH2N(NO)CH2C(NO2)3

222.6

(NO2)3C–CH2N(NO) CH2CH2-N(NO) CH2C(NO2)3

311.7

74.5

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

BDEs of C–C Bonds

203

Nitrofluoroethanes F(NO2)2–C(NO2)3

63.9

267.3

F(NO2)2–C(NO2)2F

58.4

244.3

25G3

104.6G12.6

Derived

1994NAZ/MAN

Photolysis

1991DAI/FIN(b)

Coenzyme B12, substituted H

O

O

II I + N Co N N I

CH2C6H5

N

4.5.3 Organic compounds containing sulfur atoms Table 4.5.3 C–C BDEs in Organic Compounds Containing Sulfur Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

References

Ethylthiol CH3–CH2SH

82.5G2.2

345.2G9.2

Derived from DfH0 in ref.

1986PED/NAY

1-Propanethiol C2H5–CH2SH

80.9G2.4

338.5G10.0

Derived from DfH0 in ref.

1986PED/NAY

1-Butanethiol C3H7–CH2SH

81.1G2.5

339.3G10.5

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-1-propanethiol iso-C3H7–CH2SH

80.6G2.5

337.2G10.5

Derived from DfH0 in ref.

1986PED/NAY

1-Pentanethiol nC4H9–CH2SH

81.2G2.5

339.7G10.5

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-1-butanethiol sec-C4H9–CH2SH

80.0G2.5

334.7G10.5

Derived from DfH0 in ref.

1986PED/NAY (continued)

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

204

Comprehensive Handbook of Chemical Bond Energies

Table 4.5.3 (continued) C–C BDEs in Organic Compounds Containing Sulfur Atom(s)

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

3-Methyl-1-butanethiol iso-C4H9–CH2SH

80.5G2.5

336.8G10.5

Derived from DfH0 in ref.

1986PED/NAY

2,2-Dimethyl-1-propanethiol tert-C4H9–CH2SH

78.7G2.5

329.3G10.5

Derived from DfH0 in ref.

1986PED/NAY

1-Hexanethiol nC5H11–CH2SH

80.3G2.5

336.0G10.5

Derived from DfH0 in ref.

1986PED/NAY

1-Heptanethiol nC6H13–CH2SH

80.2G2.5

335.6G10.5

Derived from DfH0 in ref.

1986PED/NAY

Phenylmethane-1-thiol C6H5–CH2SH

93.2G2.5

389.9G10.5

Derived from DfH0 in ref.

1986PED/NAY

1,2-Ethanethiol HSCH2–CH2SH

74.9G2.8

313.4G11.7

Derived from DfH0 in ref.

1986PED/NAY

Ethyl methyl sulphide CH3–CH2SCH3

82.0G2.0

343.1G8.4

Derived from DfH0 in ref.

1986PED/NAY

Methyl propyl sulphide C2H5–CH2SCH3

80.8G2.0

338.1G8.4

Derived from DfH0 in ref.

1986PED/NAY

Ethyl phenyl sulphide CH3–CH2SC6H5

80.9G2.0

338.5G8.4

Derived from DfH0 in ref.

1986PED/NAY

Dibenzyl sulphide C6H5–CH2SC6H5

97.1G2.0

406.3G8.4

Derived from DfH0 in ref.

1986PED/NAY

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

References

BDEs of C–C Bonds

4.6

205

C–C BDEs in radicals

Table 4.6 C–C BDEs in Radicals

The broken bonds (boldfaceZdissociated group) C–C

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 1998CHA

(1) Derived from DfH0 in ref. (2) Derived from DfH0 in ref.

(1) 1998CHA

(3) PD

(3) 2000CHO/BIS

601.9G19.3

GIB MS

1999LU/TOS

188.7G0.2

789.6G1.0

Derived from EA in ref.

1996NIST

(1) 139.1

582

Derived from DfH0 in ref.

(1) 1994GIN/FIN

(2) 168.4

705

(1) 135.5

567

(2) 162.2

679

(3) 137.4G3.5

575.0G14.5

595.63

(2) 147.8G3.7

618.3G15.4

(1) 175.5

734

(2) 167.9

703

(1) 135.3 (2) 118.5 (3) 108.6G3.5

566 496 454.4G14.5

4

(1) 169.3 (2) 164.4

708 688

5

(2) 116.1

486

6

(2) 168.2

704

CC–C (also see Chapter 24)

143.9G4.6

CK–C (also see Chapter 24)

C2–C2

3

C2–C3

References

(1) Derived from DfH0 in ref. (2) Spectroscopy

(1) 142.36

C–Cx xZ2

Methods (reference in parentheses)

(2) 2000LU/TOS

(2) 1994GIN/FIN

(2) 1998CHA

(1) Derived from DfH0 in ref. (2) Derived from DfH0 in ref. (3) PD

(1) 1994GIN/FIN (2) 1998CHA (3) 2000CHO/BIS

(continued)

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

206

Comprehensive Handbook of Chemical Bond Energies

Table 4.6 (continued) C–C BDEs in Radicals

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

C2–C4

133.1

557

Derived from DfH0 in ref.

1994GIN/FIN

C3–C3

(1) 83.7

350

(1) 1994GIN/FIN

(2) 76.6G4.6

320.3G19.3

(1) Derived from DfH0 in ref. (2) PD

133.4

558

Derived from DfH0 in ref.

1994GIN/FIN

(1) 214.9G6.7 (2) 198.3G3.5

899.2G28.0 829.8G14.5

(1) KER (2) MF

(1) 2004GLU/LEU (2) 2005CON/GLU

41

(1) 216.1G5.8 (2) 202.9G3.5

904.0G24.1 849.1G14.5

43

(1) 212.4G6.2 (2) 198.3G3.5

888.6G26.1 829.8G14.5

45

(1) 220.2G5.3 (2) 205.2G3.5

921.4G22.2 858.7G14.5

47

(1) 227.1G6.2 (2) 209.8G3.5

950.4G26.1 878.0G14.5

49

(1) 205.5G6.5 (2) 204.1G3.5

859.7G27.0 853.9G14.5

51

(1) 223.0G7.4 (2) 205.2G3.5

933.0G30.9 858.7G14.5

53

(1) 229.2G6.5 (2) 209.8G3.5

959.0G27.0 878.0G14.5

55

(1) 223.5G6.5 (2) 211.0G3.5

934.9G27.0 882.8G14.5

57

(1) 258.7G5.3 (2) 228.3G3.5

1082.5G22.2 955.2G14.5

59

(1) 187.5G5.8 (2) 198.3G3.5

784.4G24.1 829.8G14.5

61

(1) 208.2G5.5 (2) 215.6G4.6

871.2G23.2 902.1G19.3

C3–C4

C(C)x–C2 xZ39

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

(2) 2000CHO/BIS

BDEs of C–C Bonds

207

63

(1) 216.5G5.5 (2) 211.0G3.5

906.0G23.2 882.8G14.5

65

(1) 217.7G5.1 (2) 214.5G6.9

910.8G21.2 897.3G28.9

67

(1) 228.5G5.5

956.1G23.2

69

(1) 202.9G5.8

849.1G24.1

71

(1) 196.9G5.1

824.0G21.2

73

(1) 218.8G5.5

915.6G23.2

75

(1) 218.1G6.0

912.7G25.1

77

(1) 223.9G5.5

936.9G23.2

79

(1) 201.5G5.5

843.3G23.2

81

(1) 203.2G6.0

850.0G25.1

83

(1) 209.4G5.1

876.1G21.2

85

(1) 207.8G6.5

869.3G27.0

87

(1) 224.4G5.8

938.8G24.1

178.5G0.5

746.8G2.1

CHbC% %%

CH2aC

164.3G4

687.4G16.7

CH2aC%H

164.5G1

688.3G4.2

100.0G0.5

418.4G2.1

CH3–C%H2 %

CH2aCH-C H2

124.0G1.1

518.8G4.6

CH3–C%aCH2

80.1G4

335.1G16.7

CH3–CHaC%H

25.8G1.6

107.9G6.7

CH3–CH2C%H2 CH3–C(CH3)aC%H2

23.7G1 23.3G1

99.2G4.2 97.5G4.2

CH3–CH2C%HCH3

23.8G1

99.6G4.2

CH3–CH2C HCH2CH3

23.8G1

99.6G4.2

CH3–C(CH3)2C%H2

22.1G1.5

92.5G6.3

23.9G1.5

100.0G6.3

22.3G1

93.3G4.2

CH2CHCH2–CH2C H2

10.5G2.0

43.9G8.4

CH3CH2CH2CH2– CH2C%H2

23.1G1.5

96.7G6.3

CH3CH2–CH2C%HCH3

21.3G1.5

89.1G6.3

CH3CH2CH2– CH2C%HCH3

21.8G2

91.2G8.4

%

%

CH3–CH2C (CH3)2 %

CH3CH2–CH2C H2 %

Derived

This volume

Derived from DfH0 in ref.

1996NIST

Derived from DfH0 in ref.

1996NIST

(continued)

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

208

Comprehensive Handbook of Chemical Bond Energies

Table 4.6 (continued) C–C BDEs in Radicals

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

CH3CH2CH2CH2– CH2C%HCH3

21.8G2

91.2G8.4

CH3CH2CH2CH2CH2– CH2C%HCH3

21.5G2

90.0G8.4

(CH3)2C–CH2C(CH3)2

21.2G1.4

88.7G6

CH2CH–CHC%H

38.7G2.0

161.9G8.4

%

34.9G2.0

146.0G8.4

%

CH2CHC HCH2– CH2CH3

33.1G2.0

138.5G8.4

CH2CHC%HCH2– CH2CH2CH2CH3

32.7G3

136.8G12.6

C6H5C%HCH2–CH2CH3

31.3G3

131.0G12.6

C6H5CH2–CH2CHCH3

9.2G2

38.5G8.4

FC–C

122G6

510G25

F2C–CF

63.4G2.3

265.3G9.6

FHC–CF

107.2G4

448.5G16.7

F2C–CH

121.5G2.5

508.4G10.5

F3C–CF2

58.6G2

245.2G8.4

CH3–CF2

63.9G2.5

267.4G10.5

F3CF2C–CF2

K361

K1510

Cl3C–CCl2

62.6G2

261.9G8.4

H3C–CCl2

78.8G1.5

329.7G6.3

H3C–CBr2

78.9G2

CH2CHC HCH2–CH3

CH3–CH2C%HCl %

CH2Br–CH2C H2 %

CH3–CH2C HBr

Methods (reference in parentheses)

References

Derived from DfH0 in ref.

1996NIST

Derived

This volume

Derived

This volume

330.1G8.4

Derived

This volume

26.6G2

111.3G8.4

1996NIST

24.7G2

103.3G8.4

Derived from DfH0 in ref.

28.3G2

118.4G8.4

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BDEs of C–C Bonds

209

C–CO

(1) 76.4 (2) 53.8G0.6

319.6 225.0G2.5

Derived from DfH0 in ref

(1) 1996NIST (2) 1998CHO/MOR

OCC–CO

(1) 64.6

270.1

CC–C(O)O

127.3G3

532.6G12.6

Derived

1974GUR/KAR

CH–CO

74.2G0.7

310.2G2.9

Derived

1996MOR/OSB

CH3–CO

(1) 11.1

46.4

(1) Derived

(1) This volume

CH2Cl–CO

(1) 6.6

27.5 (2) FP

(2) 1995MAR/SZE

Derived from DfH0 in ref

1996NIST

Derived from DfH0 in ref.

1996NIST

CHCl2–CO

(1) 0.1

0.3

CF3–CO

(2) 12.4G1

51.9G4.2

CH3CH2–CO CH2CH–CO

(1) 9.7 (1) 24.0

40.5 100.4

CH2C(CH3)–CO

(1) 14.9

62.3

CH3CH2CH2–CO

(1) 10.5

43.9

(CH3)2CH–CO

(1) 9.9

41.4

(CH3)3C–CO

(1) 9.7

40.6

C6H5–CO

(1) 24.7

103.3

24.7G2.5

103.3G10.5

24.4G2.5

102.1G10.5

20.3G3

84.9G12.6

CH3–CH2C (O)

21.8G2.5

91.2G10.5

CH3–C(O)C%H2

22.3G2.5

93.3G10.5

18.2G3

76.1G12.6

37.8G3

158.2G12.6

C H2CH2–CN

58.8G3.5

246.0G14.6

CH3–CH2O%

12.3G1

51.5G4.2

2.1

8.8

CH3–CH2C%HOH %

HOCH2–CH2C H2 %

CH3–CH(OH)C H2 %

%

tC4H9–C(O)C H2 %

C6H5–C(O)C H2 %

CF3–CHFO

% %

CH3CH2–CH2O

9.6G2

40.2G8.4

%

CH3–CH(CH3)O

5.9G1

24.7G4.2

CH3–CCl(CH3)O%

2.6G2

10.9G8.4

(continued)

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

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Table 4.6 (continued) C–C BDEs in Radicals

The broken bonds (boldfaceZdissociated group) CH3CH2CH2–CH2O% %

CH3CH2–CH(CH3)O %

CH3–C(CH3)2O

CH2aCH–CH2O

%

C6H5–CH2O%

CH3–C(O)O%

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

12.9G3

54.0G12.6

4.2G2

17.6G8.4

3.4G3

14.2G12.6

24.8G3

103.8G12.6

27.3G3

114.2G12.6

(1) K16.0G3

K66.9G12.6

(2) K21.0G1.2, 0 K K87.8G4.8

Methods (reference in parentheses)

References

Derived from DfH0 in ref.

1986PED/NAY

(1) Derived from DfH0 in ref. (2) Photodetach.

(1) 2003BLA/ELL (2) 2004LU/CON

CF3–C(O)O%

K14.8G3

K61.9G12.6

Derived from DfH0 in ref.

1995TAK/PAS

C6H5–C(O)O%

K3.2G3

K13.4G12.6

Derived from DfH0 in ref.

2003BLA/ELL

C6H5–CH2N%H

26.0G3

108.8G12.6

1996NIST

33G5

138G21

Derived from DfH0 in ref.

31.3G5

131G21

29.2G5

122G21

36.1G5

151G21

%

CH3–CH2S

H3CH2–CH2S

%

CH3–CH(CH3)S% %

C6H5–CH2S

Note: (1) The BDEs in the clusters and complexes of C-, Si-, Ge-, Sn-, and Pb-ions are listed in Chapter 24. (2) The BDEs in the clusters and complexes of N-, P-As-, Sb-, and Bi-ions are listed in Chapter 25. (3) The BDEs in the clusters and complexes of O-, S-, Se-, Te-, and Po-ions are listed in Chapter 26. (4) The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27. (3) The BDEs in the clusters and complexes of O-, S-, Se-, Te-, and Po-ions are listed in Chapter 26. (4) The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27.

7366—CHAPTER 4—5/2/2007—20:05—BSARAVANAN—15360—XML MODEL B – pp. 147–210

chapter five

BDEs of C–halogen bonds 5.1

C–F bonds

Table 5.1 C–F BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Cyanogen fluoride F–CN

(1) 112.3G1.2 (2) 115.4

469.9G5.0 482.8

(1) AE (2) Der. from DfH0 in ref.

(1) 1978DAY/GOW (2) 1996NIST

Tetrafluoromethane F–CF3

(1) 130.5 (2) 130.7G0.5

546.0 546.8G2.1

Derived

(1) 1975CHE/ROD (2) 1998RUS/MIC

Trifluoromethane F–CHF2

(1) 126.0 (2) 127 (3) 127.6G1.4

527.2 531.4 533.9G5.9

(1) Derived (2) Bromination (3) Review

(1) 1975CHE/ROD (2) 1987TSC/PAD (3) 2001LAZ/PRO

Difluoromethane F–CH2F

(1) 119.0 (2) 118.6G2.1

497.9 496.2G8.8

(1) Derived (2) Review

(1) 1975CHE/ROD (2) 2001LAZ/PRO

Chlorofluoromethane F–CF2Cl

(1) 117G6 (2) 123 (3) 122.3

489.5G25 514.6 511.7

(1) Kinetics (2) Derived (3) Der. from DfH0 in ref.

(1) 1972FOO/TAI(b) (2) 1975CHE/ROD (3) 1996NIST (continued)

211

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Table 5.1 (continued) C–F BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Trifluorobromomethane F–CF2Br

120.4G5

504G21

Derived from DfH0 in ref.

1991GUR/VEY

Dichlorofluoromethane F–CFCl2

(1) 110G6 (2) 115.2G2.5

460G25 482.0G10.5

(1) 1972FOO/TAI(b) (2) 1998CHA

(3) 120.3

503.4

(1) Kinetics (2) Der. from DfH0 in ref. (3) PIMS

Chlorodifluoromethane F–CHFCl

110.5G2.4

462.3G10.0

Derived

1987TSC/PAD

Trichlorofluoromethane F–CCl3

(1) 106G5 (2) 101.9 (3) 105G1

444G21 426.3 439.3G4

(1) Review (2) Derived (3) Der. from DfH0 in ref.

(1) 1970DAR (2) 1975CHE/ROD (3) 1998CHA

Dichlorofluoromethane F–CHCl2

106.7G5.5

446G23

Derived from DfH0 in ref.

1991GUR/VEY

Chlorofluoromethane F–CH2Cl

111.2G2.3

465.3G9.6

Derived

1987TSC/PAD

Bromochlorodi fluoromethane F–CFClBr

114.5G4

479G17

Derived from DfH0 in ref.

1991GUR/VEY

Bromochloro fluoromethane F–CHClBr

107.5G4

450G17

Derived from DfH0 in ref.

1991GUR/VEY

7366—CHAPTER 5—3/2/2007—13:46—BSARAVANAN—15361—XML MODEL B – pp. 211–253

(3) 1997SHE/QI

BDEs of C–Halogen Bonds

213

Bromodichloro fluoromethane F–CCl2Br

104.7G5

438G21

Derived from DfH0 in ref.

1991GUR/VEY

Dibromochloro fluoromethane F–CClBr2

100G5

418G21

Derived from DfH0 in ref.

1991GUR/VEY

Tribromofluoromethane F–CBr3

99.0G5

414G21

Derived from DfH0 in ref.

1991GUR/VEY

Dibromofluoromethane F–CHBr2

105.8G5

443G21

Derived from DfH0 in ref.

1991GUR/VEY

Bromofluoromethane F–CH2Br

111.3G4

466G17

Derived from DfH0 in ref.

1991GUR/VEY

Triiodofluoromethane F–CI3

109.6G10

459G42

Derived from DfH0 in ref.

1991GUR/VEY

Diiodofluoromethane F–CHI2

114G9

477G38

Derived from DfH0 in ref.

1991GUR/VEY

Fluoroiodomethane F–CH2I

%110.0

%460.2

IR CL

2002ARU/VIJ

Fluoromethane F–CH3

(1) (2) (3) (4)

108G5 109.9 112.8 110.0G2.0

452G21 459.8 472.0 460.2G8.4

(1) (2) (3) (4)

(1) (2) (3) (4)

(5) 109.8G1.2

459.4G5.0

124.6

521.3

Fluoroethyne F–CbCH

Review Derived Review Der. from DfH0 in ref. (5) Review

Derived from DfH0 in ref.

1970DAR 1975CHE/ROD 1988LIA/BAR 1998CHA

(5) 2001LAZ/PRO

1996NIST (continued)

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Table 5.1 (continued) C–F BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Difluoroethyne F–CbCF

124G5

519G21

Review

1996ZAR/WES

Tetrafluoroethylene F–CFaCF2

130.6G3

546.4G12.6

Derived from DfH0 in ref.

2002CRC

Chlorotrifluoroethylene F–CClaCF2

110

460

PD

2000LEE/WAN

Hexafluoroethane F–CF2CF3

(1) 126.8G1.8 (2) 127.2G1.5

530.5G7.5 532.2G6.3

(1) Derived (2) Review

(1) 1982MCM/GOL (2) 2001LAZ/PRO

457.7

Derived

1975CHE/ROD

1,1,1,2-Tetrafluoroethane 109.4 F–CH2CF3

Pentafluoroethane F–CHFCF3

128.2G2.3

536.4G9.6

Combined

2005YAN/HUA(b)

1,1,2-Trifluoroethane F–CHFCH2F

120.9G3.2

505.7G13.2

Review

2005GIA

1,1,2-Trifluoroethane F–CH2CHF2

109.6G3.7

458.4G15.6

Review

2005GIA

1,1,2,2-Tetrafluoroethane 123.8G4.3 F–CHFCHF2

518.2G18.0

Review

2005GIA

522.5G8.6

Review

2005GIA

1,1,1-Trifluoroethane F–CF2CH3

124.9G2.1

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BDEs of C–Halogen Bonds

215

Vinyl fluoride F–C2H3

123.7G3

517.6G12.6

Derived from DfH0 in ref.

1986PED/NAY

Fluoroethane F–C2H5

(1) 107.7 (2) 111.7G2

450.6 467.4G8.4

(1) Derived (2) Der. from DfH0 in ref.

(1) 1975CHE/ROD (2) 2004KOR/LIE

(E)-1-fluoropene (E)-F–CHaCHCH3

124.1G1.5

519.2G6.3

Derived from DfH0 in ref.

1996NIST

(Z)-1-fluoropene (Z)-F–CHaCHCH3

124.9G1.5

522.6G6.3

Derived from DfH0 in ref.

1996NIST

1-Fluopropane F–C3H7

(1) 111.1G3 (2) 113.5G2

464.8G12.6 474.9G8.4

Derived from DfH0 in ref.

(1) 1986PED/NAY (2) 1998SMI

2-Fluopropane F–iso-C3H7

(1) 110.1G5 (2) 115.5G2

460.7G21 483.3G8.4

Derived from DfH0 in ref.

(1) 1986PED/NAY (2) 2004KOR/LIE

2-Fluoro-2-methylpropane F–tert–C4H9

118.5G2

495.8G8.4

Derived from DfH0 in ref.

2004KOR/LIE

Fluoro-cyclo-hexane F–cyclo-C6H11

117.5G1.5

491.4G6.3

Derived from DfH0 in ref.

1996NIST

Fluorobenzene F–C6H5

125.6G2

525.5G8.4

Derived from DfH0 in ref.

1986PED/NAY

Hexafluorobenzene F–C6F5

(1) 114 (2) 116G6

477.0 485G25

Derived

(1) 1975CHO/GOL (2) 2004CAR/KOY (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 5.1 (continued) C–F BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

(Fluoromethyl)benzene F–CH2C6H5

98.7G1

412.8G4.2

Derived

2003VER/KRA

Formyl fluoride F–COH

(1) 119.0G2.5

497.9G10.5

(1) 1998CHA

(2) %115.2

%482

(1) Der. from DfH0 in ref. (2) UV photolysis

Fluoroformyl fluoride F–COF

(1) 127.9G3 (2) 129.6G3

535.1G12.6 542.2G12.6

(1) 1995BUC/JOH (2) 1996ASH/APP

(3) 122.0

510.3

(1) PIMS (2) Der. from DfH0 in ref. (3) Derived

Chloroformyl fluoride F–COCl

115.8

484.5

Derived from DfH0 in ref.

1998CHA

Acetyl fluoride F–C(O)CH3

122.3G3

511.7G12.6

Derived from DfH0 in ref.

2002CRC

Nitrofluoroalkanes F–C(NO2)3 F–C(NO2)2F F–C(NO2)2CH3 F–C(NO2)2C(NO2)3 F–C(NO2)FC(NO2)2F F–C(NO2)2C(NO2)2F

101.8 113.5 105.7 116.4 118.4 107.0

426.1 474.7 442.4 486.9 495.2 447.5

Derived

1994NAZ/MAN

F–C60 F–C70

%86.8 %89.4

%363 %374

Derived

1997BOL/PON

7366—CHAPTER 5—3/2/2007—13:50—BSARAVANAN—15361—XML MODEL B – pp. 211–253

(2) 1999MAU/DIE

(3) 2004JAN/ROS

BDEs of C–Halogen Bonds

F–C

217

122.8G2.4

513.8G10.0

–CF

121.1G3

506.6G12.6

–CCl

117.5G4.5

491.6G18.8

–CH

127.6G3.1

533.9G13

Derived

This volume

–CF2

85.8G2

359.0G8.4

–CCl2

94.3G3

394.6G1.6

–CClF

93.1G3.8

389.5G15.9

–CClBr

91.3G3

382.0G12.6

–CHF

110.3G3.2

461.5G13.4

–CHCl

111.5G3

466.5G12.6

–CH2

119.9G1.1

501.7G4.6

104G6

435G25

Derived

This volume

F–CFC%F

69.9G3

292.5G12.6

71.2G3

297.9G12.6

Derived from DfH0 in ref.

1996NIST

–CFC%H –CHC%F

61.7G3

258.2G12.6

–CF2C%F2

75.0G3

313.8G12.6

–CHFC F2

64.6G3

270.3G12.6

–CH2C%F2

44.3G3

185.4G12.6

F–CC%

%

%

–CF2C HF

68.4G3

286.2G12.6

–CH2C%HF

43.6G3

182.4G12.6

–CF2C%H2

60.4G3

252.7G12.6

–CHFC%H2

54.9G3

229.7G12.6

–CH2C H2

45.7G3

191.2G12.6

–CClFC%F2

62.2G3

260.2G12.6

F–CF2O%

27G1

113.0G4.2

Re-evaluated

2000REI/PRA

F–C%(O)

31.1G3

130.1G12.6

Derived

This volume

F–C% (O)CH2

63.4G2.0

265.3G8.4

Derived from DfH0 in ref.

1996NIST

F–CO2

12.9

54.1

Derived from DfH0 in ref.

1995TAK/PAS

%

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218

5.2

Comprehensive Handbook of Chemical Bond Energies

C–Cl bonds

Table 5.2 C–Cl BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Cyanogen chloride Cl–CN

(1) 100.8G1.2 (2) 101.0G2.0

421.7G5.0 422.6G8.4

(1) AP (2) Der. from DfH0 in ref.

(1) 1978DAY/GOW (2) 2002CRC

Chlorotrifluoromethane Cl–CF3

(1) (2) (3) (4)

360.2G3.3 360.7G12.6 372.8 365.3G3.8

(1) (2) (3) (4)

(1) (2) (3) (4)

Chlorodifluoromethane Cl–CHF2

87.0G2

364G8

Derived from DfH0 in ref.

Chlorofluoromethane Cl–CH2F

84.7G2.8

354.4G11.7 Derived

1987TSC/PAD

Dichlorodifluoro methane Cl–CF2Cl

(1) 76G2 (2) 73.4G2.5 (3) 79.8G2.5

(1) 1972FOO/TAI(b) (2) 1989CHE/ALB (3) 1998CHA

(4) 83.9G2.3

318.0G8.4 (1) Kinetics 307.1G10.5 (2) ElCD 333.9G10.5 (3) Der. from DfH0 in ref. 351.2G9.6 (4) PI MS

Trichlorofluoromethane Cl–CFCl2

(1) 72G2 (2) 70.5 (3) 76.7G2

301.2G8.4 295.0 320.9G8.4

(1) 1972FOO/TAI(b) (2) 1989CHE/ALB (3) 1998CHA

Dichlorofluoromethane Cl–CHFCl

(1) 82.7G3.2 (2) 83.4

346.0G13.4 (1) Derived 348.9 (2) ECD

86.1G0.8 86.2G3 89.1 87.3G0.9

Kinetics Kinetics ECD Derived

(1) Kinetics (2) ECD (3) Der. from DfH0 in ref.

7366—CHAPTER 5—3/2/2007—13:50—BSARAVANAN—15361—XML MODEL B – pp. 211–253

1967COO/WHI 1983MAR/PAR 1989CHE/ALB 1998RUS/MIC

1996NIST

(4) 1997SHE/QI

(1) 1987TSC/PAD (2) 1989CHE/ALB

BDEs of C–Halogen Bonds

219

Tetrachloromethane Cl–CCl3

(1) (2) (3) (4) (5)

70.4G1 70.8G1.3 73.3 71.0 70.9

294.6G4.2 296.2G5.4 306.8 297.2 296.6

(1) Bromination (2) Correlation (3) PI (4) PIMS (5) Review

(1) (2) (3) (4) (5)

1973MEN/GOL 1978KAT/RAJ 1996LI/RAN(c) 1996LI/RAN 2001LAZ/PRO

Trichloromethane Cl–CHCl2

(1) (2) (3) (4) (5)

76.2 80.9G1 73.6 76.6G1.5 74.4G0.5

318.8 338.5G4.2 307.9 320.5G6.3 311.1G2.0

(1) (2) (3) (4) (5)

Correlation Derived ECD Review TPEPICO

(1) (2) (3) (4) (5)

1978KAT/RAJ 1987TSC/PAD 1989CHE/ALB 2001LAZ/PRO 2006LAG/BAE(b)

Dichloromethane Cl–CH2Cl

(1) (2) (3) (4) (5)

80.9G1.0 77.9 79.1 80.8 80.8G0.8

338.5G4.2 325.9 331.0 338.1 338.0G3.3

(1) (2) (3) (4) (5)

Derived ECD Photolysis Review TPEPICO

(1) (2) (3) (4) (5)

1987TSC/PAD 1989CHE/ALB 1994TZE/LEE 2001LAZ/PRO 2005LAG/KER

Bromodichloro fluoromethane Cl–CFClBr

76.7G4

321G17

Derived from DfH0 in ref.

1991GUR/VEY

Bromochloromethane Cl–CHClBr

73.7G4

308G17

Derived from DfH0 in ref.

1991GUR/VEY

Bromotrichloromethane Cl–CBrCl2

68.6G2.5

287G10.5

Derived from DfH0 in ref.

1996NIST

Dibromodichloro methane Cl–CBr2Cl

65.6G4

274G17

Derived from DfH0 in ref.

1991GUR/VEY

Tribromochloromethane Cl–CBr3

64.8G2.5

271G10.5

Derived from DfH0 in ref.

1991GUR/VEY

Dibromochloromethane Cl–CHBr2

71.5G5

299G21

Derived from DfH0 in ref.

1991GUR/VEY (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 5.2 (continued) C–Cl BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom)

kcal/mol

kJ/mol

(1) 74.9

313.4

(2) 79.5G1.1

332.8G4.6

Chlorotriiodomethane Cl–CI3

76.6G10

Chlorodiiodomethane Cl–CHI2

Chloroiodomethane Cl–CH2I

Methods

References

(1) Der. from DfH0 in ref. (2) TPEPICO

(1) 1996NIST

321G42

Derived from DfH0 in ref.

1991GUR/VEY

79.5G7.5

333G32

Derived from DfH0 in ref.

1991GUR/VEY

(1) %72.0 (2) 82.7G6.5

%301.2 346G27

(1) 2002ARU/VIJ (2) 1991GUR/VEY

(3) 78.4G1.6

328.2G6.9

(1) IR CL (2) Der. from DfH0 in ref. (3) TPEPICO

Chloromethane Cl–CH3

83.7G0.4

350.2G1.7

Derived from DfH0 in ref.

1986PED/NAY

Dichloroethyne Cl–CbCCl

106G12

443G50

Derived from DfH0 in ref.

1998CHA

Chloroethyne Cl–CbCH

104.1G2

435.6G8.4

Derived from DfH0 in ref.

1988LIA/BAR

Bromochloromethane Cl–CH2Br

2-Chloroethanenitrile Cl–CH2CN

Chlorotrifluoroethylene Cl–CFaCF2

(2) 2005LAG/KER

(3) 2005LAG/KER

(1) 63.9

267.4

(1) CID

(1) 2002POU/UPS

(2) 66.4G0.7 (3) 70.5

277.9G2.9 295.0

(2) Electrochem. (3) Est by exp

(2) 2003COS/ROB (3) 2004ISS/GEN

90

377

Photodissociation

7366—CHAPTER 5—3/2/2007—13:50—BSARAVANAN—15361—XML MODEL B – pp. 211–253

2000LEE/WAN

BDEs of C–Halogen Bonds

221

(Z)-1,2-dichloroethylene (Z)-ClCHaCH–Cl

88.2

369.0

ECD

1989CHE/ALB

(E)-1,2-dichloroethylene (E)-ClCHaCH–Cl

88.4

369.9

ECD

1989CHE/ALB

1,2-Dichloroethylene g-CH2aCCl–Cl

93.4

390.8

ECD

1989CHE/ALB

1,1,2-Trichloroethylene ClCHaCCl–Cl

93.6

391.6

ECD

1989CHE/ALB

Tetrachloroethylene CCl2aCCl–Cl

91.7

383.7

ECD

1989CHE/ALB

Vinyl chloride Cl–CHaCH2

(1) 91.7G1.0

383.7G4.2

(1) 1986PED/NAY

(2) 94.8G1.2 (3) 95.6G2

396.5G4.8 400.0G8.4

(4) 93.5

391.3

(1) Der. from DfH0 in ref. (2) PI (3) Der. from DfH0 in ref. (4) Correlation

Chlorotrifluoroethylene Cl–CFaCF2

103.9G2

434.7G8.4

Derived from DfH0 in ref.

2002CRC

Chloropenta fluoroethane Cl–CF2CF3

(1) 82.7G1.7 (2) 78G2 (3) 82.0G1.2

346.0G7.1 326.4G8.4 343.1G5.0

Kinetics

(1) 1967COO/WHI (2) 1972FOO/TAI(b) (3) 1989TAC/SAL

Dichlorotetra fluoroethane Cl–CF2CF2Cl

(1) 78G2 (2) 79.2G5

326.4G8.4 Kinetics 331.4G20.9

(1) 1972FOO/TAI(b) (2) 1989TAC/SAL

(2) 1995SHE/QI (3) 1996NIST (4) 2003KRO/TUM

(continued)

7366—CHAPTER 5—3/2/2007—13:50—BSARAVANAN—15361—XML MODEL B – pp. 211–253

222

Comprehensive Handbook of Chemical Bond Energies

Table 5.2 (continued) C–Cl BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

1,1-Difluoro-1-chloroethane Cl–CF2CH3

84.8G2.1

355.0G

Review

2005GIA

1,1,1-Trichloro-2,2,2-trifluoro ethane Cl–CCl2CF3

(1) 71 (2) 73.6

297.1 307.9

Correlation

(1) 1978KAT/RAJ (2) 1995DEN

Hexachloroethane Cl–CCl2CCl3

(1) 72.6 (2) 71.7 (3) 71.5

303.8 300.0 299.2

(1) Photo chlor. (2) Correlation (3) Derived

(1) 1969FRA/HUY (2) 1995DEN (3) 1997CIO/LIU

Pentachloroethane Cl–CHClCCl3

79.0G1

330.5G4.2

Pyrolysis

1982BEN/WEI

Pentachloroethane Cl–CCl2CHCl2

(1) 67.8 (2) 74.5

283.7 311.7

(1) Derived (2) Correlation

(1) 1997CIO/LIU (2) 1995DEN

1,1,1,2-Tetrachloroethane 76.0 Cl–CCl2CH2Cl

318.0

Correlation

1995DEN

1,1,1-Trichloroethane Cl–CCl2CH3

(1) 70 (2) 78.5

292.9 328.4

Correlation

(1) 1978KAT/RAJ (2) 1995DEN

1,1-Dichloroethane Cl–CHClCH3

(1) 79.5G2.1 (2) 78.4G0.4

332.6G8.8 327.9G1.8

Derived

(1) 1997CIO/LIU (2) 1998SEE

1,2-Dichloroethane Cl–CH2CH2Cl

(1) 79.1 (2) 83.2G2.3 (3) 82.5G1.2

331.0 348.1G9.6 345.1G5.0

(1) ECD (2) Derived (3) Derived

(1) 1989CHE/ALB (2) 1997CIO/LIU (3) 1998SEE

7366—CHAPTER 5—3/2/2007—13:51—BSARAVANAN—15361—XML MODEL B – pp. 211–253

BDEs of C–Halogen Bonds

223

1,1-Bromochloroethane Cl–CHBrCH3

79.3G2.0

331.8G8.4

Derived from DfH0 in ref.

1988LIA/BAR

Chloroethane Cl–CH2CH3

(1) 84.2G0.8

352.3G3.3

(1) 1986PED/NAY

(2) 82.8

346.3

(1) Der. from DfH0 in ref. (2) Correlation

3-Chloro-1-propyne Cl–CH2CHaCH2

71.0

297.1

Correlation

2003KRO/TUM

3-Chloro-1-propene Cl–CH2CHaCH2

(1) 71.3G1.2

298.3G5.0

(1) 1986PED/NAY

(2) 71.2

297.9

(1) Der. from DfH0 in ref. (2) Correlation

3-Chloro-2-methyl-1propene Cl–CH2C(CH3)aCH2

66.2

277.0

Correlation

1995DEN

Cis-1-chloropropene cis-Cl–CHaCHCH3

95.2

398.3

Correlation

2003KRO/TUM

Trans-1-chloropropene trans-Cl–CHaCHCH3

94.5

395.3

Correlation

2003KRO/TUM

1-Chloropropane Cl–nC3H7

84.3G1.0

352.7G4.2

Derived from DfH0 in ref.

1986PED/NAY

1,3-Dichloropropane Cl–CH2CH2CH2Cl

83.4

348.9

ECD

1989CHE/ALB

2-Chloropropane Cl–iso-C3H7

(1) 84.6G1.5

354.0G6.3

(1) 1986PED/NAY

(2) 85.2

356.3

(1) Der. from DfH0 in ref. (2) Correlation

(2) 2005DEN/TUM

(2) 2003KRO/TUM

(2) 2003KRO/TUM (continued)

7366—CHAPTER 5—3/2/2007—13:51—BSARAVANAN—15361—XML MODEL B – pp. 211–253

224

Comprehensive Handbook of Chemical Bond Energies

Table 5.2 (continued) C–Cl BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

1,4-Dichloro-2-butene Cl–CH2CHaCHCH2Cl

67.0

280.3

Correlation

1995DEN

4-Chlorobutene Cl–CH2CHCHaCH2

81.9

342.7

Derived from DfH0 in ref.

1996NIST

(E)-1-chloro-2-butene (E)-Cl–CH2CHaCHCH3

74.2G1.2

310.5G5

Derived from DfH0 in ref.

1996NIST

(Z)-1-chloro-2-butene 72.9G1.2 (Z)-Cl–CH2CHaCHCH3

305.0G5

Derived from DfH0 in ref.

1996NIST

1-Chlorobutane Cl–nC4H9

84.5G1.0

353.5G4.2

Derived from DfH0 in ref.

1986PED/NAY

1-Chloro-2-methyl propane Cl–iso-C4H9

(1) 83.8G1.5

350.6G6.3

(1) 1986PED/NAY

(2) 83.7

350.3

(1) Der. from DfH0 in ref. (2) Correlation

2-Chlorobutane Cl–sec-C4H9

(1) 83.7G1.5

350.2G6.3

(2) 85.3

357.0

(1) 84.1G1.5

351.9G6.3

(2) 83.5

349.2

2-Chloro-2-methyl propane Cl–tert-C4H9

(2) 2003KRO/TUM

(1) Der. from DfH0 in ref. (2) Correlation

(1) 1986PED/NAY

(1) Der. from DfH0 in ref. (2) Correlation

(1) 1986PED/NAY

7366—CHAPTER 5—3/2/2007—13:51—BSARAVANAN—15361—XML MODEL B – pp. 211–253

(2) 2003KRO/TUM

(2) 2003KRO/TUM

BDEs of C–Halogen Bonds

3-Chloro-but-1-ene CH2CHCHCl(CH3)

225

(1) 71.7G1.5

300.0G6.3

(1) Der. from DfH0 in ref.

(1) 1996NIST

(2) 7 1.1

297.7

(2) Correlation

(2) 2003KRO/TUM

4-Chloro-but-1-ene Cl–CH2CH2CHaCH2

81.9

342.7

Correlation

2003KRO/TUM

1-Chloropentane Cl–nC5H11

(1) 83.8G1.5

350.6G6.3

(1) 1986PED/NAY

(2) 84.6

354.1

(1) Der. from DfH0 in ref. (2) Correlation

1-Chloro-2,2-dimethylpropane Cl–CH2C(CH3)3

84.2

352.1

Correlation

2003KRO/TUM

83.3

348.5

Correlation

2003KRO/TUM

84.3

352.8

1-Chloroalkanes Cl–CnH2nC1 nZ6 7 8

85.1

355.9

12

85.2

356.5

(2) 2003KRO/TUM

16

84.3

352.5

18

85.3

356.7

(1) 84.3G1.5

352.7G6.3

(1) Der. from DfH0 in ref.

(1) 1986PED/NAY

(2) 84.1

352.0

(2) Correlation

(2) 2003KRO/TUM

(2) 84.0

351.3

(1) Der. from DfH0 in ref.

(1) 1994PED

(1) 84.8G1.5 (2) 84.5

354.8G6.3 353.6

(2) Correlation

(2) 2003KRO/TUM

2-Chloro-2-methyl butane Cl–C(CH3)2(C2H5)

2-Chloroalkanes Cl–CH(CH3)(CnH2nC1) nZ3 4

(continued)

7366—CHAPTER 5—3/2/2007—13:51—BSARAVANAN—15361—XML MODEL B – pp. 211–253

226

Comprehensive Handbook of Chemical Bond Energies

Table 5.2 (continued) C–Cl BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

5

(2) 83.1

347.9

6

(2) 83.8

350.5

Chloro-cyclo-hentane Cl–cyclo-C5H9

82.4

344.9

Correlation

2003KRO/TUM

Chloro-cyclo-hexane Cl–cyclo-C6H11

(1) 86.1G2

360.2G6.5

(1) 1986PED/NAY

(2) 85.0

355.5

(1) Der. from DfH0 in ref. (2) Correlation

(1) 95.5G1.5

399.6G6.3

(1) 1986PED/NAY

(2) 95.1G2.5 (3) 94.5G2.3

(1) Der. from DfH0 in ref. 397.9G10.5 (2) ECD 395.4 (3) ECD

2-Cl

(2) 92.2

385.8

3-Cl

(2) 89.9

376.1

4-Cl

(2) 93.7

392.0

2-Me

(2) 93.7

392.0

(2) 2003KRO/TUM

Chlorobenzenes, substituted Cl

Y

YZH

2-CF3

(2) 93.0

389.1

4-CF3

(2) 93.0

389.1

3-CH3CO

(2) 92.2

385.8

4-CH3CO

(2) 91.4

382.4

3-F-4-Cl

(2) 91.6

383.3

2-CF3-4-Cl

(2) 90.3

377.8

3,5-Cl2

(2) 94.5

395.4

2,4,5-Cl3

(2) 94.4

395.0

7366—CHAPTER 5—3/2/2007—13:51—BSARAVANAN—15361—XML MODEL B – pp. 211–253

(2) 1989CHE/ALB (3) 2002CHE/CHE

BDEs of C–Halogen Bonds

227

Chloropenta fluorobenzene Cl–C6F5

91.6G2

383.3G8.4

Derived

1982MCM/GOL

Chlorocyclohexane Cl–C6H11

85.1G2

356.1G8.4

Derived from DfH0 in ref.

1986PED/NAY

Trichloro-phenyl methane Cl–CCl2C6H5

66.5

278.2

Correlation

1995DEN

Benzyl chloride Cl–CH2C6H5

(1) 72.9G2

305.0G8.4

(1) 1986PED/NAY

(2) 71.6 (3) 71.7G1.1

299.6 299.9G4.3

(1) Der. from DfH0 in ref. (2) Electrochem. (3) Derived

YZ3-F

68.5

286.8

Correlation

1998DEN

4-F

69.1

289.0

3-Cl

69.1

289.0

3-Me

69.1

289.0

4-Me

69.9

292.5

3-CF3

68.4

286.2

Electrochem.

1997BOR/DAL

(2) 1992AND/GOR (3) 2003VER/KRA

Benzyl chloride substituted CH2

Y

Cl

3-MeO

69.2

289.6

4-tert-Bu

69.8

291.9

4-CN

67.0

280.3

3,4-Cl2

68.3

285.6

3,5-Cl2

66.7

279.2

3,5-(CF3)2

66.3

277.6

Dichloromethyl benzene 68.0 C6H5CHCl–Cl

284.5

(continued)

7366—CHAPTER 5—3/2/2007—13:51—BSARAVANAN—15361—XML MODEL B – pp. 211–253

228

Comprehensive Handbook of Chemical Bond Energies

Table 5.2 (continued) C–Cl BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Trichloromethyl benzene 58.1 C6H5CCl2–Cl

243.1

Electrochem.

1997BOR/DAL

1-Chloroethylbenzene C6H5CH(CH3)–Cl

69.9G1.1

292.4G4.4

Derived

2003VER/KRA

(1-chloro-isopropyl) benzene C6H5C(CH3)2–Cl

70.0G1.5

292.8G6.3

Derived

2003VER/KRA

(2-chloroethyl)benzene Cl–CH2CH2C6H5

76.4

319.8

Correlation

2003KRO/TUM

1-Chloronaphthalene Cl–1-naphthyl

(1) 93.4G3 (2) 96.3G2.7

390.8G12.6 (1) ECD 402.9G11.3 (2) Der. from DfH0 in ref. 400.4 (3) Derived

(1) 1989CHE/ALB (2) 1986PED/NAY

(1) 1986PED/NAY

(2) 93.1

384.5G11.3 (1) Der. from DfH0 in ref. 389.5 (2) Derived

1-Adamantyl chloride Cl–1-adamantyl

(1) 83.8G3 (2) 90.4G3

350.6G12.6 Derived from 378.2G12.6 DfH0 in ref.

(1) 1999FLO/DAV (2) 2002LI/BAR

2,2,2-Trichloroethane nitrile CNCCl2–Cl

62.2

260.2

1995DEN

(3) 95.7

2-Chloronaphthalene Cl–2-naphthyl

(1) 91.9G2.7

Correlation

7366—CHAPTER 5—3/2/2007—13:51—BSARAVANAN—15361—XML MODEL B – pp. 211–253

(3) 1998GAL/PAU

(2) 1998GAL/PAU

BDEs of C–Halogen Bonds

229

2,2-Dichloroethanenitrile 70.7 CNCHCl–Cl

295.8

Carbonyl chloride Cl–C(O)Cl

318.8G8.4

Correlation

1995DEN

(1) Der. from DfH0 in ref. (2) 65.0G4.6, 0 K 272.1G19.3 (2) CID

(1) 2002CRC

Chloroformyl fluoride Cl–C(O)F

90.0

376.6

Derived from DfH0 in ref.

1998CHA

Acetyl chloride Cl–C(O)CH3

84.6G2

354.0G8.4

Derived from DfH0 in ref.

2002CRC

2-Chloroacetyl chloride Cl–CH2C(O)Cl

64.7

270.7

Correlation

1995DEN

Propanoyl chloride Cl–C(O)CH2CH3

84.4G1.5

353.3G6.3

Derived from DfH0 in ref.

1998WIN/ROW

Benzoyl chloride Cl–C(O)C6H5

81.5G2

341.0G8.4

Derived from DfH0 in ref.

2002CRC

2-Chloro-1-phenylethan- 73.9 1-one Cl–CH2C(O)C6H5

309

VLPP

1999DOR/HEM

2-Chloroacetic acid Cl–CH2C(O)OH

(1) 66.6 (2) 74.3G0.5 (3) 71.0G3

278.7 (1) Correlation 310.9G2.2 (2) Calorimetry 297.1G12.6 (3) Der. from DfH0 in ref.

(1) 1995DEN (2) 2001LAG/DIO (3) 2001DOR/NOV

2,2-Dichloroacetic acid Cl–CClHC(O)OH

67.2

281.2

1995DEN

(1) 76.2G2

Correlation

(2) 2003LIY/STY(b)

(continued)

7366—CHAPTER 5—3/2/2007—13:52—BSARAVANAN—15361—XML MODEL B – pp. 211–253

230

Comprehensive Handbook of Chemical Bond Energies

Table 5.2 (continued) C–Cl BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

2,2,2-Trichloroacetic acid 66.3 Cl–CCl2C(O)OH

kJ/mol

Methods

References

277.4

Correlation

1995DEN

2-Chloropropionic acid CH3CHClC(O)OH

71.2G0.8

298.0G3.2

Combination

2002LAG/DIO

Methyl 2-chloroacetate Cl–CH2C(O)OCH3

72.1

301.7

Correlation

1995DEN

Ethyl 2,2-dichloroacetate 68.8 Cl–CClHC(O)OC2H5

287.9

Correlation

1995DEN

Ethyl 2,2,2-trichloro acetate Cl–CCl2C(O)OC2H5

66.7

279.1

Correlation

1995DEN

Phenyl 2-chloroacetate Cl–C(O)OC6H5

(1) 81 (2) 87

338.9 364.0

(1) PAC (2) PAC, revised

(1) 1989SIM/GRI (2) 1999LAA/MUL

Diethyl 2,2-dichloro propane-1,3-dioate Cl–CCl(C(O)OEt)2

67.3

281.6

Correlation

1995DEN

Chloroacetamides Cl–CH2C(O)NH2 Cl–CClHC(O)NH2 Cl–CCl2C(O)NH2

80.7 73.3 64.1

337.7 306.8 268.2

Electrochem.

2005COS/LOU

Chloroacetamides Cl–CH2C(O)NMe2 Cl–CCl2C(O)NMe2

77.0 66.0

322.3 275.9

Electrochem.

2005COS/LOU

7366—CHAPTER 5—3/2/2007—13:52—BSARAVANAN—15361—XML MODEL B – pp. 211–253

BDEs of C–Halogen Bonds

231

Chloroacetamides Cl–CH2C(O)NEt2

77.5

324.2

Electrochem.

2005COS/LOU

Chlorothioformyl chloride Cl–C(S)Cl

63.4G0.5

265.3G2.1

Photolysis

1977OKA

Chloromethyl thiomethane Cl–CH2SCH3

72.0G0.6

301.2G2.5

Photoinozation

2001CHE?CHE

Chlorotrinitromethane Cl–C(NO2)3

(1) 73.2 (2) 72.2

306.3 302.1

(1) Derived (2) Der. from DfH0 in ref.

(1) 1994NAZ.MAN (2) 1996NIST

Electrochem.

1997BOR/DAL

Electrochem.

1997BOR/DAL

Chloromethyl pyridines X N

C

XZH X’ZH

Cl X'

70.1

293.3

H

Cl

64.1

268.2

Cl

Cl

57.6

241.0

68.6

287.0

Chloromethyl pyridines X C

N

Cl X'

XZH X’ZH H

Cl

63.5

265.7

Cl

Cl

55.9

233.9

Chloromethyl pyridines X N

C

Cl X'

(continued)

7366—CHAPTER 5—3/2/2007—13:52—BSARAVANAN—15361—XML MODEL B – pp. 211–253

232

Comprehensive Handbook of Chemical Bond Energies

Table 5.2 (continued) C–Cl BDEs

The broken bonds (boldfaceZdissociated atom) XZH X’ZH H Cl Cl Cl

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Electrochem.

1997BOR/DAL

69.9 65.8 59.3

292.5 275.3 248.1

90.5G3.5

378.7G14.6 Derived from DfH0 in ref.

2005SILMIR

86.6G3.5

362.3G14.6 Derived from DfH0 in ref.

2005SILMIR

94.4G3.2

394.9G13.4 Derived

This volume

–CF

82.6G3.8

345.6G15.9

–CCl

80.9G3.1

338.5G13.0

–CBr

87.2G15

364.8G63

–CH

93.8G2.2

392.3G9.2

Chloropyridine N 4

2 3

Cl

Chloropyrazine N N

Cl–C

Cl

–CF2

52.2G2.5

218.4G10.5

–CClF

57.7G3.8

241.4G15.9

–CCl2

66.0G2

276.1G8.4

–CBr2

67.4G3.5

282.0G14.6

–CClBr

63.2G4

264.4G16.7

–CHF

77.7G3.8

325.1G15.9

–CHCl

84.7G2.5

354.4G10.5

–CH2

94.3G1

394.6G4.2

Cl–CC%

89G7

372G29

Derived from DfH0 in ref.

This volume

Cl–CHC%H

17.5G0.5

73.2G2

Photolysis

2005GAO/ALE

7366—CHAPTER 5—3/2/2007—13:52—BSARAVANAN—15361—XML MODEL B – pp. 211–253

BDEs of C–Halogen Bonds

233

Cl–CClC%Cl

33.7G3

–CF2C%F2

35.6G3

–CF2C%HF

23.4G3

97.9G12.6

–CF2C%H2

21.1G3

88.3G12.6

–CCl2C%Cl2

17.6G3

73.6G12.6

–CHClC%Cl2

18.8G3

78.7G12.6

%

141.0G12.6 Derived from DfH0 in ref.

–CH2C Cl2

23.2G3

97.1G12.6

–CCl2C%HCl

12.2G3

51.0G12.6

–CHClC%HCl

18.3G3

76.6G12.6

–CH2C%HCl

18.4G3

77.0G12.6

–CCl2C%H2

12.3G3

51.5G12.6

–CHClC%H2

12.5G3

52.3G12.6

19.3G2

80.8G8.4

(1) 7.8G1 (2) 17.1G4.6

32.6G4 71.4G19.3

%

–CH2C H2

Cl–C%(O)

5.3

1996NIST

149.0G12.6

(1) Derived (2) CID

(1) This volume (2) 2003LIY/STY(b)

C–Br bonds

Table 5.3 C–Br BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Cyanogen bromide Br–CN

(1) 87.8G1.2 (2) 87.2G1.0

367.4G5.0 364.8G4.2

(1) AE (2) Derived from DfH0 in ref.

(1) 1978DAY/GOW (2) 1996NIST

Bromotrifluoromethane Br–CF3

(1) 70.6G3 (2) 69.6 (3) 71.0 (4) 70.8G0.3 (5) 70.8G0.7

295.4G12.6 291.2 297.1 296.2G1.3 296.2G2.9

(1) Kinetics (2) Derived (3) Correlation (4) PIMS (5) Derived

(1) 1972FER/WHI(b) (2) 1983EVA/WEE (3) 1995DEN (4) 1997ASH/RUS (5) 1998RUS/MIC

Bromodifluoromethane Br–CHF2

69G2

288.7G8.4

Bromination

1974OKA/WHI

(continued)

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Table 5.3 (continued) C–Br BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Bromofluoromethane Br–CH2F

70.5G4

295G17

Derived from DfH0 in ref.

1991GUR/VEY

Bromochlorodifluoromethane Br–CF2Cl

(1) 64.5G1.5 (2) 64.1G2

269.9G6.3 268G8

(1) Review (2) Thermolysis

(1) 1982MCM/GOL (2) 1994DEL/LOU

Difluorodibromomethane Br–CF2Br

63.8G4

270G17

Derived from DfH0 in ref.

1991GUR/VEY

Bromodichlorofluoromethane Br–CCl2F

61.6G4

257.7G17

Derived from DfH0 in ref.

1991GUR/VEY

Bromochlorofluoromethane Br–CHFCl

67.2G4

281G17

Derived from DfH0 in ref.

1991GUR/VEY

Bromotrichloromethane Br–CCl3

(1) 52G3 (2) 55.3G1

218G13 231.4G4.2

(1) Review (2) Bromination

(1) 1970DAR (2) 1973MEN/GOL

Bromodichloromethane Br–CHCl2

(1) 58.3G5

248G21

(1) 1991GUR/VEY

(2) 62.3

261

(1) Derived from DfH0 in ref. (2) Derived

(1) 65.5G4

274G17

(2) 68.0 (3) 66.3G0.9

285 277.3G3.6

Dibromochlorofluoromethane Br–CFClBr

61.4G1.2

257G5

Derived from DfH0 in ref.

2003OWE/NAU

Dibromochloromethane Br–CHClBr

57.6G5

241G21

Derived from DfH0 in ref.

1991GUR/VEY

Bromochloromethane Br–CH2Cl

(1) Derived from DfH0 in ref. (2) PD (3) TPEPICO

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(2) 2006JAW/CEM

(1) 1991GUR/VEY (2) 1994TZE/LEE (3) 2005LAG/KER

BDEs of C–Halogen Bonds

235

Dibromodichloromethane Br–CBrCl2

53.9G4

225.5G17

Derived from DfH0 in ref.

1991GUR/VEY

Tribromochloromethane Br–CBr2Cl

50.4G2.5

210.9G10.5

Derived from DfH0 in ref.

1991GUR/VEY

Tetrabromomethane Br–CBr3

(1) 56.2G1.8 (2) 57.9G4.2

235.1G7.5 242.3G8.4

(1) 1971KIN/GOL (2) 1996NIST

(3) 54.7G2.3

228.9G9.6

(1) Bromination (2) Derived from DfH0 in ref. (3) Review

Tribromomethane Br–CHBr2

(1) 64.8 (2) 65.7G3.1

271.1 274.9G13.0

(1) ECD (2) Review

(1) 1989CHE/ALB (2) 2001LAZ/PRO

Dibromomethane Br–CH2Br

(1) 69.8G2 (2) 65.8 (3) 60.0 (4) 69.3G2.4 (5) 66.0G1.3

292.0G8.4 275.3 250.9 290.0G10.0 276.1G5.3

(1) Bromination (2) ECD (3) PI (4) Review (5) TPEPICO

(1) 1987TSC/PAD (2) 1989CHE/ALB (3) 1996LI/RAN(b) (4) 2001LAZ/PRO (5) 2005LAG/KER

Bromotriiodomethane Br–CI3

62.6G11

262G46

Derived from DfH0 in ref.

1991GUR/VEY

Bromodiiodomethane Br–CHI2

67G9

280G38

Derived from DfH0 in ref.

1991GUR/VEY

Bromoiodomethane Br–CH2I

(1) 67.3G6.5

282G27

(1) 1991GUR/VEY

(2) 65.6G1.8

274.5G7.5

(1) Derived from DfH0 in ref. (2) TPEPICO

Bromomethane Br–CH3

70.3G0.5

294.1G2.1

Derived from DfH0 in ref.

1986PED/NAY

Bromoethyne Br–CbCH

98.1

410.5

Derived from DfH0 in ref.

1996NIST

(Z)-1,2-dibromoethylene (Z)-CHBraCH–Br

!83.8

!350.6

ECD

1989CHE/ALB

(3) 2001LAZ/PRO

(2) 2005LAG/KER

(continued)

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Table 5.3 (continued) C–Br BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

(E)-1,2-dibromoethylene (E)-CHBraCH–Br

!83.3

!348.5

ECD

1989CHE/ALB

Vinyl bromide Br–CHaCH2

(1) 79.4G1.5

332.2G6.3

(1) 1986PED/NAY

(2) 77G3 (3) 79.3 (4) 79.2G0.7 (5) 79.6G0.7

322.2G12.6 331.8 331.2G2.8 333.2G3.1

(1) Derived from DfH0 in ref. (2) PD (3) Correlation (4) PFI-PEPICO (5) TREPICO

(2) 1989WOD/HIN (3) 2003KRO/TUM (4) 2004QIA/LAU(b) (5) 2006LAG/BAE

2-Bromoethanenitrile Br–CH2CN

56.8

237.7

Est. by exp.

2004ISS/GEN

Bromopenta fluoroethane Br–CF2CF3

(1) 68.6G1.5 (2) 68.8 (3) 67.7G1.5

287.0G6.3 287.9 283.3G6.3

(1) Kinetics (2) Derived (3) Derived from DfH0 in ref.

(1) 1972FER/WHI (2) 1983EVA/WEE (3) 2002CRC

1,1-Dibromo-1-chloro-2,2,2trifluoroethane Br–CClBrCF3

60.0G1.5

251.0G6.3

Review

1982MCM/GOL

1,2-Dibromo-1,1,2,2tetrafluoroethane Br–CF2CF2Br

67.6G1.6, 0 K

282.8G6.7

UV photolysis

1989NAT/MIN

1-Bromo-1-chloro-2,2,2trifluoroethane Br–CHClCF3

65.7G1.5

274.9G6.3

Review

1982MCM/GOL

1-Bromo-1,1-difluoroethane Br–CF2CH3

68.6G1.3

287.0G5.4

Kinetics

1977PIC/ROD

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BDEs of C–Halogen Bonds

237

1-Bromo-2-chloroethane Br–CH2CH2Cl

69.9G2.0

292.5G8.4

Derived from DfH0 in ref.

1988LIA/BAR

1,1-Bromochloroethane Br–CHClCH3

65G2

272.0G8.4

Derived from DfH0 in ref.

1988LIA/BAR

Bromoethane Br–C2H5

(1) 70.0G1.0

292.9G4.2

(1) 1986PED/NAY

(2) 70.4

294.6

(1) Derived from DfH0 in ref. (2) Correlation

(1) 56.7G1.2

237.2G5.0

(2) 56.4

235.8

(1) 80.0G1.2

334.7G5.0

(2) 80.9G1.2 (3) 78.9

338.5G5.0 330.1

(1) 80.7G1.2

337.6G5.0

(2) 79.6

332.9

(1) 71.3G1.0

298.3G4.2

(2) 70.5

294.9

(1) 71.5G1.5

299.2G6.3

(2) 71.2

1,3-Dibromopropane Br–CH2CH2CH2Br

1-Bromo-heptafluoropropane Br–CF2CF2CF3

3-Bromo-1-propene Br–CH2CHaCH2

(E)-1-bromo-1-propene (E)-Br–CHaCHCH3

(Z)-1-bromo-1-propene (Z)-Br–CHaCHCH3

1-Bromopropane Br–nC3H7

2-Bromopropane Br–iso-C3H7

(1) Derived from DfH0 in ref. (2) Correlation

(1) Derived from DfH0 in ref. (2) Derived (3) Correlation

(1) Derived from DfH0 in ref. (2) Correlation

(1) Derived from DfH0 in ref. (2) Correlation

(2) 2003KRO/TUM

(1) 1986PED/NAY (2) 2003KRO/TUM

(1) 1986PED/NAY (2) 2002MOR/MIL (3) 2003KRO/TUM

(1) 1986PED/NAY (2) 2003KRO/TUM

(1) 1986PED/NAY (2) 2003KRO/TUM

297.7

(1) Derived from DfH0 in ref. (2) Correlation

(1) 2002CRC (2) 2003KRO/TUM

77.6

324.7

ECD

1989CHE/ALB

66.5G2.5

278.2G10.5

Kinetics

1967COO/WHI

(continued)

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Table 5.3 (continued) C–Br BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

2-Bromo-heptafluoropropane CF3CFBrCF3

(1) 65.5G1.1 (2) 65.4

274.2G4.6 273.8

(1) Review (2) Kinetics

(1) 1982MCM/GOL (2) 1983EVA/WEE

1,1,1-Tribromopropane Br–CBr2CH2CH3

60.8

254.4

Correlation

1995DEN

1-Bromobutane Br–nC4H9

(1) 70.9G1

296.6G4.2

(1) 1986PED/NAY

(2) 71.1

297.4

(1) Derived from DfH0 in ref. (2) Correlation

(2) 2003KRO/TUM

1-Bromo-2-methyl-propane Br–CH2CH(CH3)2

70.5

295.0

Correlation

2003KRO/TUM

2-Bromobutane Br–sec-C4H9

(1) 71.7G1

300.0G4.2

(1) 1986PED/NAY

(2) 71.9

300.7

(1) Derived from DfH0 in ref. (2) Correlation

(1) 70.0G1.5

292.9G6.3

(2) 69.9

3-Bromo-but-1-nen CH2aCHCHBrCH3

4-Bromo-but-1-nen Br–CH2CH2CHaCH2

2-Bromo-2-methylpropane Br–tert-C4H9

1-Bromo-alkanes Br–CnH2nC1 nZ5

(2) 2003KRO/TUM

292.4

(1) Derived from DfH0 in ref. (2) Correlation

(2) 2003KRO/TUM

55.7

233.1

Correlation

2003KRO/TUM

68.1

284.8

Correlation

2003KRO/TUM

(1) 70.5G1

295.0G4.2

(1) 1986PED/NAY

(2) 71.6

299.4

(1) Derived from DfH0 in ref. (2) Correlation

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(1) 1986PED/NAY

(2) 2003KRO/TUM

BDEs of C–Halogen Bonds

239

6

(1) 70.1G1 (2) 71.7 (3) 70.9

293.3G4.2 300.1 296.6

7

(2) 71.4

298.8

8

(2) 71.1

297.3

12

(2) 71.2

297.8

16

(2) 70.5

294.8

18

(2) 69.9

292.5

2-Bromo-alkanes Br–CH(CH3)(CnH2nC1) nZ3

(3) Correlation

(3) 2005DEN/TUM

Correlation

2003KRO/TUM

70.9

296.6

4

71.0

296.9

5 6

71.1 70.8

297.3 296.3

1-Bromo—2, 2-dimethyl-propane Br–CH2C(CH3)3

71.3

298.2

Correlation

2003KRO/TUM

2-Bromo-2-methyl-butane (CH3)2CBrC2H5

68.7

287.6

Correlation

2003KRO/TUM

Bromo-cyclo-heptane Br–cyclo-C5H9

69.6

291.1

Correlation

2003KRO/TUM

Bromo-cyclo-hexane Br–cyclo-C6H11

69.9

292.4

Correlation

2003KRO/TUM

1-Adamantyl bromide Br–1-adamantyl

70.8

296.1

Derived from DfH0 in ref.

2005BAZ/KAB

72.8

304.4

Correlation

2005DEN/TUM

1-Bromodispiro [2.1.2.0]heptane H

Br

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 5.3 (continued) C–Br BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

1-Bromodispiro[2.1.2.1]octane

H Br

Bromopentafluorobenzene Br–C6F5

71.2

297.9

Correlation

2005DEN/TUM

w78.4

w328

Derived

1996ING/WEI

Bromobenzenes, substituted

Br

Y YZH

(1) 83.5G2.5

349.4G10.5

(1) ECD

(1) 1989CHE/ALB

(2) 80.4G1.5

336.4G6.3

(2) Derived from DfH0 in ref.

(2) 1986PED/NAY

(3) Correlation

(3) 1995DEN

(1) 1986PED/NAY

(4) 1997LAA/BOR (5) 2003VER/KRA

2-F

(3) 82.0

343.1

2-Me

(3) 83.9

351.0

3-CF3

(3) 79.9

334.3

(1) 60.0G3

251.0G12.6

(2) 55.9 (3) 55.1G2.5

233.9 230.5G10.5

(4) 60.7G1 (5) 57.2G1.5

254G4 239.3G6.3

(1) Derived from DfH0 in ref. (2) Electrochemical (3) Derived from DfH0 in ref. (4) PAC (5) Derived (6) AOP

(6) 1993ZHA

Correlation

1995DEN

Bromotoluenes, substituted

CH2

Y

Br

YZp-H

p-F

(6) 58.9

246.4

p-Br

(6) 57.6

241.0

p-CN

(1) 60.9G1 (6) 54.4

255G4 227.6

p-Me

(6) 59.7

249.8

p-tert-Bu

(1) 60.0G1

251G4

m-CF3

(1) 60.9G1

255G4

63.4

265.3

(1-Bromovinyl)benzene CH2aCHBrPh

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(2) 1992AND/GOR (3) 1996NIST

BDEs of C–Halogen Bonds

241

(2-Bromovinyl)benzene Br–CHaCHPh

65.1

272.4

Correlation

1995DEN

Benzyl bromide Br–CH2C6F5

53.8G1.5

225.1G6.3

TCT

1980KOM/KRE

(1,2,2,2-Tetraethyl)benzene Br–CBr2CHBrPh

60.3

252.3

Correlation

1995DEN

(2-Bromoethyl)benzene Br–CH2CH2C6H5

64.1

268.3

Correlation

2003KRO/TUM

1-Bromoethylbenzene C6H5CH(CH3)–Br

57.4G2

240.1G8.2

Derived

2003VER/KRA

(1-Bromo-isopropyl)benzene C6H5C(CH3)2–Br

56.6G1.6

236.7G6.9

Derived

2003VER/KRA

1-Bromonaphthalene Br–1-C10H7

(1) 79.3 (2) 81.2

331.8 339.7

(1) ECD (2) Derived

(1) 1989CHE/ALB (2) 1998GAL/PAU

2-Bromonaphthalene Br–2-C10H7

81.7

341.8

Derived

1998GAL/PAU

(1,2-Dibromo-2-phenylethyl)benzene (PhCHBr)2

62.9

263.2

Correlation

1995DEN

9-Anthracenyl bromide Br–anthracenyl

77.1

322.6

Derived

1998GAL/PAU

Acetyl bromide Br–C(O)CH3

(1) 64 (2) 69.8G2

267.8 292.0G8.4

(1) Photolysis (2) Derived from DfH0 in ref.

(1) 1995SU/DIB (2) 2002CRC

(continued)

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242

Comprehensive Handbook of Chemical Bond Energies

Table 5.3 (continued) C–Br BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Benzoyl bromide Br–C(O)C6H5

(1) 64.1 (2) 66.1G2

268.2 276.6G8.4

(1) Review (2) Derived from DfH0 in ref.

(1) 1970ONE/BEN (2) 1994PED

1-Bromoacetone Br–CH2C(O)CH3

(1) 62.5 (2) 61.6G2.5

261.5 257.9G10.5

(1) VLPP (2) Derived from DfH0 in ref.

(1) 1978ZAB/BEN (2) 1996NIST

2-Bromo-1-phenylethan-1-one Br–CH2C(O)C6H5

64.8

271

VLPP

1999DOR/HEM

2-Bromoacetic acid Br–CH2C(O)OH

(1) 61.5G0.9 (2) 58.2G3

257.4G3.7 243.5G12.6

(1) 2001LAG/DIO (2) 2001DOR/NOV

(3) 64.3

269.0

(1) Calorimetry (2) Derived from DfH0 in ref. (3) Correlation

2,2,2-Tribromoacetic acid Br–CBr2C(O)OH

60.8

254.4

Correlation

1995DEN

2-Bromopropanoic acid CH3CHBrC(O)OH

61.3

256.3

Correlation

2003KRO/TUM

3-Bromopropanoic acid Br–CH2CH2C(O)OH

66.0

276.3

Correlation

2003KRO/TUM

Ethyl 2,2-dibromoacetate Br–CHBrC(O)OC2H5

62.9

263.2

Correlation

1995DEN

Ethyl 2,2,2-tribromoacetate Br–CBr2C(O)OC2H5

58.9

246.4

Correlation

1995DEN

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(3) 2003KRO/TUM

BDEs of C–Halogen Bonds

243

Diethyl 2-bromopropane-1,3dioate Br–CH(C(O)OEt)2

63.5

265.7

Correlation

1995DEN

Diethyl 2,2-dibromopropane1,3-dioate Br–CBr(C(O)OEt)2

61.4

256.9

Correlation

1995DEN

Bromotrinitromethane Br–C(NO2)3

(1) 52.9 (2) 52.2

221.2 218.4

(1) Derived (2) Derived from DfH0 in ref.

(1) 1994NAZ/MAN (2) 1996NIST

Br–C

76.0G2

318.0G8.4

Derived

This volume

–CBr

71.3G2

298.3G8.4

–CF2

36.9G3.5

154.4G14.6

–CClF

42.6G3.5

178.2G14.6

–CCl2

51.1G2.5

213.8G10.5

–CClBr

51.5G2.5

215.5G10.5 230.5G8.4

Derived from DfH0 in ref.

1996NIST

–CBr2

55.1G2

–CHCl

70.5G2.5

295.0G10.5

–CH2

79.1G0.7

331.0G2.9

6.9G2 8.5G2

28.9G8.4 35.6G8.4

Br–CH2C%H2 –CH2C%HCH3

5.4

C–I bonds

Table 5.4 C–I BDEs

The broken bonds (boldfaceZdissociated atom) Cyanogen iodide I–CN

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) 72.5G1.2 (2) 76.5

kJ/mol 303.3G5.0 320.1

Methods (1) AP (2) Der. from DfH0 in ref.

References (1) 1978DAY/GOW (2) 2002CRC (continued)

7366—CHAPTER 5—3/2/2007—13:53—BSARAVANAN—15361—XML MODEL B – pp. 211–253

244

Comprehensive Handbook of Chemical Bond Energies

Table 5.4 (continued) C–I BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom)

kcal/mol

kJ/mol

Methods

52.6G1.1 53.5 54.4G0.5 54.3G0.3 54.3G0.7

220.1G4.6 223.8 227.6G2.1 227.2G1.3 227.2G2.9

(1) (2) (3) (4) (5)

Kinetics Kinetics Kinetics PIMS Derived

References

Trifluoroiodomethane I–CF3

(1) (2) (3) (4) (5)

Difluoroiodomethane I–CHF2

57.3G6

240G25

Derived from DfH0 in ref.

1991GUR/VEY

Fluoroiodomethane I–CH2F

55.6G6

233G25

Derived from DfH0 in ref.

1991GUR/VEY

Difluorochloroiodo methane I–CClF2

49.6G6.5

208G27

Derived from DfH0 in ref.

1991GUR/VEY

Difluorobromoiodo methane I–CF2Br

49.5G5

207G21

Derived from DfH0 in ref.

1991GUR/VEY

Difluorodiiodomethane I–CF2I

(1) %53, at 0 K (2) %51.3G2

%222 %214.6G8

PD

(1) 1991WAN/FEL (2) 1993BAU/FEL

Fluorodichloroiodo methane I–CCl2F

47.2G5.5

197G23

Derived from DfH0 in ref.

1991GUR/VEY

Fluorochloroiodo methane I–CHClF

52.8G5.5

221G23

Derived from DfH0 in ref.

1991GUR/VEY

7366—CHAPTER 5—3/2/2007—13:53—BSARAVANAN—15361—XML MODEL B – pp. 211–253

(1) (2) (3) (4) (5)

1975OKA/WHI 1984AHO/WHI 1991SKO/DYM 1997ASH/RUS 1998RUS/MIC

BDEs of C–Halogen Bonds

245

Trichloroiodomethane I–CCl3

40.1G10

168G42

Derived from DfH0 in ref.

1991GUR/VEY

Dichloroiodomethane I–CHCl2

45.1G5

189G21

Derived from DfH0 in ref.

1991GUR/VEY

Chloroiodomethane I–CH2Cl

(1) 48.8G0.2 (2) 52.0G0.9 (3) 53G1

204.2G0.8 217.4G3.6 221.8G4.2

(1) Kinetics (2) TPEPICO (3) UVPD

(1) 1996SKO/DYM (2) 2005LAG/KER (3) 2005ZHA/NG

Bromochlorofluoroiodo methane I–CFClBr

46.9G5.5

196G23

Derived from DfH0 in ref.

1991GUR/VEY

Bromochloroiodo methane I–CHClBr

44.7G5.5

187G23

Derived from DfH0 in ref.

1991GUR/VEY

Bromodichloroiodo methane I–CBrCl2

40.8G5.5

171G23

Derived from DfH0 in ref.

1991GUR/VEY

Dibromochloroiodo methane I–CBr2Cl

37.0G6.5

155G27

Derived from DfH0 in ref.

1991GUR/VEY

Tribromoiodomethane I–CBr3

36.4G6.5

152G27

Derived from DfH0 in ref.

1991GUR/VEY

Dibromoiodomethane I–CHBr2

44.2G6.5

185G27

Derived from DfH0 in ref.

1991GUR/VEY

Bromoiodomethane I–CH2Br

(1) 52.1G6.5

218G27

(1) 1991GUR/VEY

(2) 52.4G1.3

219.2G5.4

(1) Derived from DfH0 in ref. (2) TPEPICO

(2) 2005LAG/KER (continued)

7366—CHAPTER 5—3/2/2007—13:53—BSARAVANAN—15361—XML MODEL B – pp. 211–253

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Comprehensive Handbook of Chemical Bond Energies

Table 5.4 (continued) C–I BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Tetraiodomethane I–CI3

45.8G12

192G50

Derived from DfH0 in ref.

1991GUR/VEY

Triiodomethane I–CHI2

52.7G8

220.5G33

Derived from DfH0 in ref.

1991GUR/VEY

Diiodomethane I–CH2I

(1) 51.9G2

217.1G8.4

(1) 1993CAR/LAY

(2) 50.6 (3) 51.8G1.9

211.7 216.9G7.9

(1) Der. from DfH0 in ref. (2) Correlation (3) TPEPICO

Iodomethane I–CH3

(1) 57.1G0.5

238.9G2.1

(1) Der. from DfH0 in ref. (2) Photo dissociation

(1) 1986PED/NAY

(2) 55.6G0.5, 0 K 232.5G1.9

(2) 1995DEN (3) 2005LAG/KER

(2) 1999EPP/PAR

2-Iodoethanenitrile I–CH2CN

44.7G1.5

187.0G6.3

PES

2000LAF/SZA

Pentafluoroiodoethane I–CF2CF3

(1) 51.2G1

214.2G4.2

Kinetics

(1) 1976WU/ROD

(2) 52.3 (3) 52.4G0.5

218.8 219.2G2.1

1,2-Diiodo-1,1,2,2tetrafluoro ethane I–CF2CF2I

52G1.6, at 0 K

217.6G6.7

UV photolysis

1984KRA/BUT

1,1,1-Trifluoro-2iodoethane I–CH2CF3

(1) 56.3G1

235.6G4.2

(1) Iodination

(1) 1973WU/ROD

(2) 52.9

221.3

(2) Correlation

(2) 1995DEN

(2) 1984AHO/WHI (3) 1991SKO/DYM

7366—CHAPTER 5—3/2/2007—13:53—BSARAVANAN—15361—XML MODEL B – pp. 211–253

BDEs of C–Halogen Bonds

247

1-Chloro-1,1,2-trifluoro2-iodo-ethane I–CHFCClF2

48.3G0.5

202G2

Kinetics

1998SKO/DYM

1,1-Difluoro-1iodoethane I–CF2CH3

52G1

217.6G4.2

Review

1982MCM/GOL

1-Fluoro-1,1diiodoethane I–CFICH3

52.1G1

218.0G4.2

Iodination

1976PIC/ROD

1-Chloro-2-iodo-ethane I–CH2CH2Cl

54.2

226.8

Correlation

1995DEN

1-Chloro-2-bromoethane I–CH2CH2Br

53.0

221.8

Correlation

1995DEN

Pentafluoro-2iodopropane CF3CFICF3

51.4

215.1

Kinetics

1984AHO/WHI

Iodoethyne I–CCH

78.8

329.9

Correlation

2003KRO/TUM

Iodoethylene I–CHaCH2

(1) 61.9G1.0 (2) 66.0

259.0G4.2 276.3

(1) PF (2) Correlation

(1) 1989CAO/ZHA (2) 2003KRO/TUM

Iodoethane I–C2H5

(1) 55.8G1.5

233.5G6.3

(1) 1986PED/NAY

(2) 55.4

231.9

(1) Der. from DfH0 in ref. (2) Correlation

(2) 2005DEN/TUM

44.1

184.6

Correlation

2003KRO/TUM

3-Iodo-prop-1-yne I–CH2CCH

(continued)

7366—CHAPTER 5—3/2/2007—13:53—BSARAVANAN—15361—XML MODEL B – pp. 211–253

248

Comprehensive Handbook of Chemical Bond Energies

Table 5.4 (continued) C–I BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kJ/mol

Methods

(1) 44.4G1.5

185.8G6.3

(2) 42.7

178.5

(1) Der. from DfH0 in ref. (2) Correlation

(1) 68.6G2

287.0G8.4

(2) 67.5

282.3

(1) 67.0G2

280.3G8.4

(2) 65.9

275.6

(1) 56.6G1

236.8G4.2

(2) 56.9

238.0

(1) 56.1G1.5

234.7G6.3

(2) 55.1

1,3-Diiodopropane I–CH2CH2CH2I

1-Iodononafluorobutane I–C4F9

3-Iodo-1-propene I–CH2CHaCH2

(Z)-1-iodo-1-propene I–CHaCHCH3

(E)-1-iodo-1-propene I–CHaCHCH3

1-Iodopropane I–nC3H7

kcal/mol

(1) Der. from DfH0 in ref. (2) Correlation

(1) Der. from DfH0 in ref. (2) Correlation

(1) Der. from DfH0 in ref. (2) Correlation

References (1) 1986PED/NAY (2) 2003KRO/TUM

(1) 1986PED/NAY (2) 2003KRO/TUM

(1) 1986PED/NAY (2) 2003KRO/TUM

(1) 1986PED/NAY (2) 2003KRO/TUM

230.6

(1) Der. from DfH0 in ref. (2) Correlation

(2) 2005DEN/TUM

54.4

227.6

Correlation

1995DEN

49.2

205.8

Kinetics

1991SKO/DYM

1-Iodo-2-methyl-propane 57.3 I–iso-C4H9

239.8

Correlation

2003KRO/TUM

2-Iodopropane I–iso-C3H7

7366—CHAPTER 5—3/2/2007—13:53—BSARAVANAN—15361—XML MODEL B – pp. 211–253

(1) 1986PED/NAY

BDEs of C–Halogen Bonds

249

2-Iodobutane I–sec-C4H9

56.9

238.0

Correlation

2003KRO/TUM

2-Iodo-2-methylpropane I–tert-C4H9

(1) 54.3G1.5

227.2G6.3

(1) 1986PED/NAY

(2) 54.3

227.0

(1) Der. from DfH0 in ref. (2) Correlation

(2) 2003KRO/TUM

3-Iodo-but-1-nen CH3CHICHaCH2

40.3

168.7

Correlation

2003KRO/TUM

4-Iodo-but-1-nen I–CH2CH2CHaCH2

55.8

233.7

Correlation

2003KRO/TUM

56.2

235.0

Correlation

2003KRO/TUM

1-Iodo-alkanes I–CnH2nC1 nZ4 5

56.3

235.7

6

56.4

236.0

7

56.2

235.2

8 12

56.1 56.1

234.9 234.9

16

56.2

234.9

18

56.1

234.9

57.1

239.1

Correlation

2003KRO/TUM

55.5

232.3

Correlation

2003KRO/TUM

Correlation

2003KRO/TUM

1-Iodo-2,2imethylpropane I–CH2C(CH3)3

2-Iodo-alkanes CH3CHICnH2nC1 nZ3 4

55.5

232.4

5

55.7

233.2

6

55.4

231.8

54.3

227.0

2-Iodo-2-methyl-butane (CH3)2CIC2H5

(continued)

7366—CHAPTER 5—3/2/2007—13:53—BSARAVANAN—15361—XML MODEL B – pp. 211–253

250

Comprehensive Handbook of Chemical Bond Energies

Table 5.4 (continued) C–I BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

Iodo-cyclo-propane I–cyclo-C3H5

64.5G2

269.9G8.4

Review

2001ARN/COS

Iodo-cyclo-heptane I–cyclo-C5H9

55.4

231.8

Correlation

2003KRO/TUM

Iodo-cyclo-hexane I–cyclo-C6H11

(1) 55.5G1.5

232.2G6.3

(1) 1986PED/NAY

(2) 54.8

229.2

(1) Der. from DfH0 in ref. (2) Correlation

Iodobenzene I–C6H5

65.0G1

272.0G4.2

Derived from DfH0 in ref.

1986PED/NAY

Pentafluoroiodobenzene I–C6F5

(1) 65.4G2 (2) !72.1

273.6G8.4 !301.7

(1) TCT (2) ECD

(1) 1976KOM/KRE (2) 1989CHE/ALB

(1) 65.9 (2) 67.4

275.7 281.9

Correlation

(1) 1995DEN (2) 2003KRO/TUM

2-Cl 2-Br

(1) 65.1 (1) 64.2 (2) 65.5

272.4 268.6 273.9

2-I

(1) 63.6 (2) 67.3

266.1 281.6

2-Me

(1) 65.7 (2) 67.2

274.9 281.0

2-CF3

(1) 63.2

264.4

2-NH2

(1) 66.7 (2) 70.3

279.1 294.3

(2) 2003KRO/TUM

Iodobenzenes substituted I

Y

YZ2-F

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BDEs of C–Halogen Bonds

251

2-NO2

(1) 65.6

274.5

2-MeO

(1) 66.6 (2) 68.0

278.7 284.7

2-Et

(1) 65.5 (2) 67.0

274.1 280.2

2-EtO

(1) 66.7 (2) 68.0

279.1 284.6

2-Ph

(1) 64.8 (2) 66.2

271.1 276.8

2,6-Me2

(1) 65.9 (2) 67.4

275.7 281.8

Benzyl iodide I–CH2C6H5

(1) 45.4

190.0

(1) Shock wave

(1) 1990HIP/TRO

(2) 43.9G2

183.7G8.4

(2) 1996NIST

(3) 44.9G1.1

187.8G4.8

(2) Der. from DfH0 in ref. (3) Derived

(2-Iodoethyl)benzene I–CH2CH2C6H5

54.9

229.7

Correlation

1995DEN

(1-Iodoethyl)benzene C6H5CH(CH3) –I

42.1G1

176.1G4.3

Derived

2003VER/KRA

(1-Iodoisopropyl)benzene C6H5C(CH3)2–I

42.1G1

176.1G4.3

Derived

2003VER/KRA

1-Iodonaphthalene I–1-naphthyl

(1) 65.6G2.5

274.5G10.5

(1) 1986PED/NAY

(2) 65.0 (3) 66.8

272.0 279.5

(1) Der. from DfH0 in ref. (2) Derived (3) Correlation

(1) 65.0G2.5

272.0G10.5

(2) 66.3 (3) 67.1

277.4 280.9

2-Iodonaphthalene I–2-naphthyl

(1) Der. from DfH0 in ref. (2) Derived (3) Correlation

(3) 2003VER/KRA

(2) 1998GAL/PAU (3) 2003KRO/TUM

(1) 1986PED/NAY (2) 1998GAL/PAU (3) 2003KRO/TUM (continued)

7366—CHAPTER 5—3/2/2007—13:54—BSARAVANAN—15361—XML MODEL B – pp. 211–253

252

Comprehensive Handbook of Chemical Bond Energies

Table 5.4 (continued) C–I BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods

References

1-Adamantyl iodide I–1-adamantyl

53.7

224.7

Correlation

1995DEN

Iodoacetonitrile I–CH2CN

44.7G2.0

187.0G8.4

Derived from DfH0 in ref.

2000LAF/SZA

Iodomethyl methyl ether 54.8G2 I–CH2OCH3

229.4G8.4

Derived from DfH0 in ref.

198NIST

Iodomethyl methyl sulfide I–CH2SCH3

51.8G1.5

216.8G6.3

Derived from DfH0 in ref.

1996NIST

Acetyl iodide I–C(O)CH3

53.3G2

223.0G8.4

Derived from DfH0 in ref.

2002CRC

3-Iodo-2butanone I–CH(CH3)C(O)CH3

46.9G2

196.3G8

Derived from DfH0 in ref.

1996NIST

Benzoyl iodide I–C(O)C6H5

50.7G2

212.1G8.4

Derived from DfH0 in ref.

1994PED

Iodoacetic acid I–CH2C(O)OH

(1) 51.2

214.2

(1) Correlation

(1) 1995DEN

(2) 47.2G0.6

197.5G2.7

(2) Calorimetry

(2) 2001LAG/DIO

3-Iodopropanioc acid I–CH2CH2C(O)OH

54.5

228.0

Correlation

1995DEN

Ethyl 2-iodoacetate I–CH2C(O)OC2H5

51.9

217.1

Correlation

1995DEN

7366—CHAPTER 5—3/2/2007—13:54—BSARAVANAN—15361—XML MODEL B – pp. 211–253

BDEs of C–Halogen Bonds

Iodotrinitromethane I–C(NO2)3

253

(1) 34.7

145.0

(1) Derived

(1) 1994NAZ/MAN

(2) 34.6

144.8

(2) Der. from DfH0 in ref.

(2) 1996NIST

68.7

287.4

Correlation

2005DEN/TUM

68.8

288.0

(1) 63.1

264.0

Correlation

(1) 1995DEN

(1) 65.2 (2) 66.6

272.8 278.6

(1) 64.9 (2) 66.3

271.5 277.4

60.5G8.5

253.1G35.6

Thiophene iodide I

S

C–I at 2 site 3

Pyridine iodide 4 3 1 2 N

I

C–I at 2 site 3

4

I–C –CI

49.8G16

208.4G66.9

–CI2

35.9G14

150.2G60

–CH2

63.9G2.1

267.4G8.8

(2) 2005DEN/TUM

Derived

This volume

Note: (1) The BDEs in the clusters and complexes of C–, Si–, Ge–, Sn–, and Pb-ions are listed in Chapter 24. (2) The BDEs in the clusters and complexes of N–, P–As–, Sb–, and Bi-ions are listed in Chapter 25. (3) The BDEs in the clusters and complexes of O–, S–, Se–, Te–, and Po-ions are listed in Chapter 26. (4) The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27.

7366—CHAPTER 5—3/2/2007—13:54—BSARAVANAN—15361—XML MODEL B – pp. 211–253

chapter six

BDEs of O–X bonds 6.1 6.1.1

O–H bonds O–H bonds in non-phenols

6.1.1.1 O–H bonds in ROH Table 6.1.1.1 O–H BDEs in ROH BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Water

(1) 119.30G0.05

499.15G0.21

(1) Recommended

(1) 1994BER/ELL

HO–H

(2) 118.88G0.01

497.38G0.06

(2) PD

(2) 2000HAR/HWA

DfH0(R)Z8.91G0.1

(3) 118.81G0.07

497.10G0.29

(3) Recommended

(3) 2002RUS/WAG

(4) 118.82G0.16

497.14G0.67

(4) Shock tube

(4) 2002HER/HAN

O–H

(3) 102.75G0.07

429.91G0.29

Oxygen deuteride DO–D

(1) 121.1

506.7

(1) Review

(1) 1974GUR/KAR

(2) 121.01G0.06

506.31G0.24

(2) PI

(2) 2001HAR/YAN

O–D

(3) 102.68

429.64

(3) Spectroscopy

(3) 1979HUB/HER

Oxygen tritide TO–T

122.2

511.3

Review

1974GUR/KAR

O–T

104.4

436.8

Hypofluorous acid

101.6

425.1

Derived from DfH0 in

1998CHA

(37.3G0.3)

FO–H

ref.

DfH0(R)Z26G2.4 (109G10)

(continued)

255

7366—CHAPTER 6—5/2/2007—10:50—JEBA—15362—XML MODEL B – pp. 255–368

256

Comprehensive Handbook of Chemical Bond Energies

Table 6.1.1.1 (continued) O–H BDEs in ROH BDEs (boldfaceZ recommended data;

The broken bonds DfH0(R), kcal/mol (kJ/mol) Hypochlorous acid

Methods

reference in parentheses)

(boldfaceZdissociated atom)

kcal/mol 94.1

(reference in

kJ/mol 393.7

parentheses) Derived from DfH0 in

References 1998CHA

ref.

ClO–H DfH0(R)Z24.29G0.03 (101.63G0.1)

Hypobromous acid

96.8

405.0

Derived from DfH0 in

2001IUPC

ref.

BrO–H DfH0(R)Z30.2G0.4 (126.2G1.7)

Hypoiodomous acid

96.4

403.3

Derived from DfH0 in

2001IUPC

ref.

IO–H DfH0(R)Z27.7G1.2 (115.9G5.0)

Methanol

(1) 104.4G1

436.8G4.2

(1) Kinetics

(1) 1974BAT/CHR

CH3O–H

(2) 104.2G0.9

436.0G3.8

(2) Recommended

(2) 1994BER/ELL

DfH0(R)Z5.0G0.5 (21.0G2.1) CD3O–H

(3) 104.9G0.7

439G3

(3) CID

(3) 1999DET/ERV

(4) 104.6G0.7

437.7G2.8

(4) GPA, revised

(4) 2002ERV/DET

(5) 105.2G0.7

440.2G3

(5) GPA

(5) 2003REE/HAR

(6) 104.2G2.2

436G9

(6) PES, derived

(6) 2000RAM/DAV

Trifluoromethanol

(1) 109

456.1

(1) Pyrolysis

(1) 1982BAT/WAL

CF3O–H

(2) 120G3

502.1G12.6

(2) FT-IR

(2) 1993WAL/HUR

DfH0(R)ZK151.8G1.7

(3) 124.7G3.6

521.7G15.1

(3) FA MS

(3) 1996HUE/DUN

(4) 117.5

491.6

(4) PIMS

(4) 1997ASH/APP

(5) 118.8

497.1

(5) Recommended

(5) 2000REI/PRA

105.9G2.1

443.1

PES

1983OAK/JON

Vinyl alcohol

(1) 85

355.6

(1) FT-ICR

(1) 2001BOU/CHA

CH2aCHO–H

(2) 84.1G1.2

352G5

(2) PA

(2) 2001BOU/ROO

(K635.1G7.1)

Ethyn-1-ol HCbCO–H

DfH0(R)Z4.4G0.3 (18.4G1.3)

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BDEs of O–X Bonds

257

Ethanol

(1) 104.2G1

436.0G4.2

(1) Pyrolysis

(1) 1974BAT/CHR

C2H5O–H

(2) 104.6G0.8

437.6G3.3

(2) Recommended

(2) 1994BER/ELL

DfH0(R)ZK3.3G1.0

(3) 105.2G1.2

440G5

(3) CID

(3) 1999DET/ERV

(4) 104.7G0.8

438.1G3.3

(4) GPA, revised

(4) 2002ERV/DET

(5) 105.4G1.4

441.0G5.9

(5) GPA

(5) 2003REE/HAR

C2H5O–D

(1) %105.9G0.5

%443.1G2.1

(1) PD

(1) 1999XU/AMA

CD3CH2O–H

(2) 103.9G0.2

437.7G1.0

(2) GPA

(2) 1993DAN/MOT

CH3CD2O–H

(2) 104.1G0.2

435.6G1.0

(K13.6G4.0)

Ethanol

CD3CD2O–H

2,2,2-Trifluoroethan-1-ol

(2) 104.1G0.2

435.6G1.0

(3) 104.2G2.4

436G10

(3) PES, derived

(3) 2000RAM/DAV

107.0G2.5

447.7G10.5

GPA

2003REE/HAR

CF3CH2O–H

1-Propanol

(1) 105.9G2

443.1G8.4

(1) Review

(1) 1973BEN/ONE

nC3H7O–H

(2) 103.4G1

432.6G4.2

(2) Pyrolysis

(2) 1974BAT/CHR

DfH0(R)ZK7.2G2

(3) %103.5G0.5

%443G2

(3) PD

(3) 2003ZHO/YUA

(4) 103.2

431.9

(4) Correlation

(4) 2005DEN/TUM

(K30.1G8.4)

2-Propanol

(1) 104.7G1

438.1G4.2

(1) Pyrolysis

(1) 1974BAT/CHR

iso-C3H7O–H

(2) 103.9

434.7

(2) AOP

(2) 1996BOR/LIU

DfH0(R)ZK11.6G0.8

(3) 105.9G1.0

443G4

(3) CID

(3) 1999DET/ERV

(4) 105.7G0.7

442.3G2.8

(4) GPA, revised

(4) 2002ERV/DET

(5) %104.0G0.5

%435G2

(5) PD

(5) 2003ZHO/YUA

106.5

445.6

Re-analyzed

2004TUM/DEN(b)

1-Butanol

(1) 101.9G1

426.3G4.2

(1) Pyrolysis

(1) 1974BAT/CHR

nC4H9O–H

(2) 103.3

432.3

(2) Correlation

(2) 2005DEN/TUM

(K48.5G3.3)

1,1-Dimethyl-2-chloropropanol ClCH2Me2CO–H

DfH0(R)ZK15 (K62.8)

2-Butanol

(1) 105.5G1

441.4G4.2

(1) Pyrolysis

(1) 1974BAT/CHR

sec-C4H9O–H

(2) 103.9

434.8

(2) Correlation

(2) 2005DEN/TUM

DfH0(R)ZK16.6 (69.5)

(continued)

7366—CHAPTER 6—5/2/2007—10:50—JEBA—15362—XML MODEL B – pp. 255–368

258

Comprehensive Handbook of Chemical Bond Energies

Table 6.1.1.1 (continued) O–H BDEs in ROH BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

recommended data;

Methods

reference in parentheses) kcal/mol

(reference in

kJ/mol

parentheses)

References

tert-Butyl alcohol

(1) 105.1G1

439.7G4.2

(1) Pyrolysis

tert-C4H9O–H

(2) 105.5

441.4

(2) AOP

(1) 1974BAT/CHR (2) 1996BOR/LIU

DfH0(R)ZK20.5G0.9

(3) 105.5

441.4

(3) PAC

(3) 2000REI/PRA

(4) 106.3G0.7

444.9G2.8

(4) GPA, revised

(4) 2002ERV/DET

(5) 106.8G1.0

446.9G4.2

(5) GPA

(5) 2003REE/HAR

Neo-pentyl alcohol

(1) 102.3G1

428.0G4.2

(1) Pyrolysis

(1) 1974BAT/CHR

tert-BuCH2O–H

(2) 104.2

436.1

(2) Correlation

(2) 2004TUM/DEN(b)

Correlation

(K85.8G3.8)

2,2-Dimethyl-propanol

(1) 104.2

436

EtCMe2O–H

(2) 105.1

439.7

(1) 2004TUM/DEN(b)

1,1-Dimethyl-butanol

104.1

435.4

Correlation

2004TUM/DEN(b)

103.8

434.4

Correlation

2004TUM/DEN(b)

103.0

431.1

Correlation

2004TUM/DEN(b)

103.6

433.6

Correlation

2004TUM/DEN(b)

104.0G2.0

435.1G8.4

GPA

2004FAT/KAS

104.0G2.0

435.1G8.4

GPA

2004FAT/KAS

(2) 2005DEN/TUM

nPrCMe2O–H

1,1,2,2-Tetramethyl-ethanol iso-PrCMe2O–H

1,1-Diethyl-ethanol MeCEt2O–H

2,2,3,3-Tetramethyl-propanol Me3CCMe2O–H

2,3,3-Trimethyl-propanol Me3CCH(Me)CO–H

2-Ethyl-3,3-dimethylpropanol Me3CCH(Et)CO–H

7366—CHAPTER 6—5/2/2007—10:50—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

259

1-Methyl-cyclo-pentan-1-ol O

H

Me

101.6

425.1

Correlation

2005DEN/TUM

103.9

434.8

Correlation

2004TUM/DEN(b)

104.8

438.5

Correlation

2005DEN/TUM

cyclo-Penen-1-ol H

O

cyclo-Hexanol H

O

Benzyl alcohol

(1) 101.7

425.5

(1) AOP

(1) 1996BOR/LIU

C6H5CH2O–H

(2) 105.8G2.1

442.7G8.8

(2) GPA

(2) 2004FAT/KAS

104.7G0.2

438.2G1.0

Correlation

2006DEN/DEN

104.2

435.8

Correlation

2004TUM/DEN(b)

104.6

437.6

Correlation

2005DEN/TUM

103.1

431.5

Derived

2002MIR/LEB

92

384.9

AOP

1994BOR/SAT

DfH0(R)Z32.5G3 (136.0G12.6)

1,1-Dimethybenzyl alcohol C6H5CMe2O–H

1,1-Dimethyl-2-phenylpropanol PhCH2CMe2O–H

1,1-Dimethy-p-NO2-benzyl alcohol p-NO2-C6H4CMe2O–H

1-Adamantanol O

H

1 2

1,3-cyclo-Hexadione O

O

H

(continued)

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260

Comprehensive Handbook of Chemical Bond Energies

Table 6.1.1.1 (continued) O–H BDEs in ROH BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) Ethane-1,1-diol

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

106.8G1.5

446.9G6.3

Electrochemical

2002MER/LIN

107.7G1.5

450.6G6.3

Electrochemical

2002MER/LIN

88

368.2

AOP

1994BOR/SAT

AOP

1997BOR/ZHA

CH3C(OH)O–H

Propane-2,2-diol (CH3)2C(OH)O–H

Tropolone

O O

H

In enols, R1R2CZCR(OH) MesZmesityl R1

R2

R

Mes

Mes

H

82.2

343.9

Mes

Mes

Mes

82.6

345.6

Mes

Mes

Me3Si

82.4

344.8

Mes

Mes

Ph

79.9

334.3

Mes

Mes

iPr

78.6

328.9

Mes

Mes

tBu

78.3

327.6

Mes

Ph

Mes

83.7

350.2

Me5C6

Me5C6 H

82.3

344.3

H

H

83.0

347.3

Me

Nitrous acid

(1) 78.3G0.5

327.6G2.1

(1) Review

(1) 1976BEN

H–ONO

(2) 79.0

330.7

(2) Derived from DfH0

(2) 2001IUPAC

DfH0(R)Z7.91 (33.10)

t,perp-HOONO H–OONO

in ref.

71.5

299.2

Derived from DfH0 in ref.

7366—CHAPTER 6—5/2/2007—10:51—JEBA—15362—XML MODEL B – pp. 255–368

2002HIP/NAS

BDEs of O–X Bonds

Hydroxylamine

261

75–77

314–322

Electrochemical

2006LIN/MER

(1) 101.2 (2) 102.0

423.4 426.8

Derived from DfH0 in

(1) 1998CHA (2) 2001IUPAC

45.2

189

Derived from DfH0

H–ONH2

Nitric acid H–ONO2

ref.

DfH0(R)Z17.6 (73.7G1.4)

Hyponitrite

2004POS/SHA

in ref.

H–ONNOH

Isocyanic acid H–ONC

90.3

377.7

Derived

2004JAN/ROS

54.9G1

229.7G8

Derived from DfH0

2005DEN

DfH0(R)Z92.4 (386.6)

HOS radical

in ref.

H–OS DfH0(R)Z1.2G0.3 (5.0G1.3)

Sulfuric acid

105.5G3.5

441.4G14.6

GPA

2004FAT/KAS

60.1G10

252G42

Derived from DfH0

1989GUR/VEY

H–OSO2OH DfH0(R)ZK122.3 (K511.7)

HOP radical H–OP

Metaphosphoric acid

in ref.

111.3G3.0

465.7G12.6

GPA

2004FAT/KAS

118.3

495

Derived

1998BEC/WAL

H–OPO2

2,2-Dimethylsilaethanol H–OSiMe3

7366—CHAPTER 6—5/2/2007—10:51—JEBA—15362—XML MODEL B – pp. 255–368

262

6.1.1.2

Comprehensive Handbook of Chemical Bond Energies

O–H bonds in RC(O)OH

Table 6.1.1.2 O–H BDEs in RC(O)OH BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) Formic acid

recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 111.7G0.3 467.5G1.2

HC(O)O–H (2) 112G3 DfH0(R)ZK30G3 (K125.5G12.6) (3) 111.5

468.6G12.6 466.3

Methods (reference in parentheses)

References

(1) PD

(1) 1997LAN/BAT

(2) Recommended (3) Derived

(2) 2003BLA/ELL (3) 2004JAN/ROS

Acetic acid

(1) 112

468.6

(1) AOP

(1) 2000XIA/ZHU

CH3C(O)O–H

(2) 110.0

460.2

(2) DEA

(2) 2003SAI/PEL

DfH0(R)ZK43G3 (K179.9G12.6) (3) 112G3

Chloroacetic acid

468.6G12.6

(3) Review

(3) 2003BLA/ELL

(4) 110.1

460.7

(4) Derived

(4) 2004JAN/ROS

(5) 106.5

445.8

(5) Correlation

(5) 2005TUM/DEN

109.7

458.9

Correlation

2005DEN/TUM

108.1G3

452.3G12.6

Derived from DfH0

1996NIST

ClCH2C(O)O–H

Trifluoroacetic acid CF3C(O)O–H

in ref.

DfH0(R)ZK90.5 (K797.0)

Propanoic acid C2H5C(O)O–H

(1) 113 (2) 105

472.8 439.3

(1) AOP (2) Correlation

(1) 2000XIA/ZHU (2) 2005TUM/DEN

Butanoic acid

105.1

439.8

Correlation

2005DEN/TUM

iso-Butanoic acid

(1) 113

472.8

(1) AOP

(1) 2000XIA/ZHU

iso-C3H7C(O)O–H

(2) 104

435.2

(2) Correlation

(2) 2005TUM/DEN

Pentanoic acid

105.7

442.1

Correlation

2005DEN/TUM

104.0

435.2

Correlation

2005DEN/TUM

C3H7C(O)O–H

C4H9C(O)O–H

iso-Pentanoic acid iso-C4H9C(O)O–H

7366—CHAPTER 6—5/2/2007—10:51—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

263

Hexaanoic acid C5H11C(O)O–H

105.0

439.3

Correlation

2005DEN/TUM

Heptanoic acid

106.2

444.4

Correlation

2005DEN/TUM

104.8

438.5

Correlation

2005DEN/TUM

105.9

443.0

Correlation

2005DEN/TUM

104.6

437.8

Correlation

2005DEN/TUM

106.5

445.8

Correlation

2005DEN/TUM

107.3

448.8

Correlation

2005DEN/TUM

106.6

446.2

Correlation

2005DEN/TUM

106.6

446.2

Correlation

2005DEN/TUM

106.0

443.7

Correlation

2005DEN/TUM

C6H13C(O)O–H

Octanoic acid C7H15C(O)O–H

Nonanoic acid C8H17C(O)O–H

Decanoic acid C9H19C(O)O–H

Dodecanoic acid C11H23C(O)O–H

cyclo-Propanecarboxylic acid O

H

O

cyclo-Butanecarboxylic acid O

H

O

2-cyclo-Butylacetic acid O O

H

cyclo-Pentanecarboxylic acid O O

H

(continued)

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264

Comprehensive Handbook of Chemical Bond Energies

Table 6.1.1.2 (continued) O–H BDEs in RC(O)OH BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

2-cyclo-Pentylacetic acid O O

107.0

447.7

Correlation

2005DEN/TUM

105.6

441.7

Correlation

2005DEN/TUM

107.0

447.7

Correlation

2005DEN/TUM

105.6

441.8

Correlation

2005DEN/TUM

H

cyclo-Hexanecarboxylic acid O O

H

2-cyclo-Hexalacetic acid O O

H

cyclo-Heptanecarboxylic acid O O

H

Benzoic acid

(1) 105

439.3

(1) AOP

(1) 1994BOR/SAT

C6H5C(O)O–H

(2) 111

464.4

(2) AOP

(2) 2000XIA/ZHU

DfH0(R)ZK12G4 (K50.2G16.7)

(3) 112G3

468.6G12.6

(3) Derived

(3) 2000WAN/BRO

(4) 111G4

464.4G16.7

(4) Recommended

(4) 2003BLA/ELL

(5) 106.2

444.2

(5) Correlation

(5) 2005TUM/DEN

(1) 112

468.6

(1) AOP

(1) 2000XIA/ZHU

(2) 107.3

449.1

(2) Correlation

(2) 2005DEN/TUM

m-Br

(2) 107.5

449.6

o-Br

(2) 106.5

445.5

p-Cl

(2) 105.7

442.1

m-Cl

(2) 107.3

448.9

o-Cl

(2) 106.4

445.3

(1) 110

460.2

(2) 107.8

451.1

Benzoic acids, substituted O Y O

YZp-Br

p-Me

H

7366—CHAPTER 6—5/2/2007—10:52—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

265

m-Me

(2) 107.2

448.6

o-Me

(2) 106.2

444.2

p-MeO

(1) 109

456.1

(2) 106.8

447

(2) 107.0

447.8

m-MeO o-MeO

(2) 106.0

443.5

p-NO2

(1) 119

497.9

(2) 107.2

448.3

o-NO2

(2) 107.2

448.5

p-t-Bu

(1) 107.1

448.2

3,5-Me2

(1) 106.5

445.4

107.1

448.0

Correlation

2005DEN/TUM

104.4

436.9

Correlation

2005DEN/TUM

111G5

464.4G21

Photodetach.

2000WAN/BRO

108G5

451.9G21

Photodetach.

2000WAN/BRO

115

481.2

103.4G0.6

432.5G2.5

Correlation

2006DEN/DEN

103.3

431.9

Correlation

2005DEN/TUM

2-Phenylacetic acid PhCH2C(O)O–H

3-Phenylpro–2-ynoic acid PhCbCC(O)O–H

Nicotinic acid, substituted CH 3OO2C

O

N

C O

H

Pyridium carboxyled species X

O C

+N

O

H

CH 3

XZH K

C(O)O

Alkoxy acids n-PrOC(O)O–H

Alkoxy acids sec-BuOC(O)O–H

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Comprehensive Handbook of Chemical Bond Energies

6.1.1.3

O–H bonds in ROOH

Table 6.1.1.3 O–H BDEs in ROOH BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

recommended data; reference in parentheses)

Methods (reference in

kcal/mol

kJ/mol

Hydroperoxide

(1) 88.2G1.0

369.0G4.2

(1) Review

(1) 1983SHU/BEN

HOO–H DfH0(R)Z3.2G0.5

(2) 88.4G1.2 (3) 87.9G0.8

269.9G5.0 367.8G3.3

(2) GIB MS (3) GPA

(2) 1990FIS/RM(b) (3) 1998LIT/RUS

(4) 87.8G0.5

367.4G2.1

(13.4G2.1)

parentheses)

References

(4) PES

(4) 2002RAM/BLA

(5) 87.49G0.07 366.06G0.29

(5) Derived

(5) 2006RUS/PIN

Hydroperoxy radical

(1) 48.3G1.2

202.1G5.0

(1) GIB MS

(1) 1990FIS/ARM(b)

OO–H

(2) 48.8G0.8

204.2G3.3

(2) Derived

(2) 1998LIT/RUS

(3) 48.2G0.8

201.7G3.3

(3) Derived from

(3) 2001IUPC

DfH0 in ref. (4) Derived

(4) 2006RUS/PIN

(4) 49.16G0.06 205.69G0.25

Methyl hydroperoxide

(1) 88.5G0.5

370.3G2.1

(1) VLPP

(1) 1984KON/BEN(b)

CH3OO–H

(2) 87.2

365

(2) Electrochemical

(2) 1996JON

DfH0(R)Z4.8G1.2 (20.1G5.0)

(3) 87.9G1.1

367.8G4.6

(3) GPA

(3) 2001BLA/RAM

(4) 86.0

359.8

(4) Derived

(4) 2004JAN/ROS

CD3OO–H

(3) 87.8G1.0

367.4G4.2

Trifluoromethyl hydroperoxide

91.5

383

Electrochemical

1996JON

90.6

379

Electrochemical

1996JON

92.3

386

Electrochemical

1996JON

CF3OO–H

DfH0(R)ZK151.8 (K635.0) Fluoromethyl hydroperoxide CH2FOO–H

Trichloromethyl hydroperoxide CCl3OO–H DfH0(R)ZK5.0G2.1 (K20.9G8.9)

7366—CHAPTER 6—5/2/2007—10:53—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

Dichloromethyl hydroperoxide

267

91.5

383

Electrochemical

1996JON

90.6

379

Electrochemical

1996JON

Tribromomethyl hydroperoxide CBr3OO–H

91.5

383

Electrochemical

1996JON

Bromomethyl hydroperoxide

90.6

379

Electrochemical

1996JON

CHCl2OO–H DfH0(R)ZK4.6G2.7 (K19.2G11.2)

Chloromethyl hydroperoxide CH2ClOO–H DfH0(R)ZK1.2G3.3 (K5.1G13.6)

CH2BrOO–H

Ethyl hydroperoxide

(1) 86.8

363

(1) Electrochemical

(1) 1996JON

C2H5OO–H

(2) 84.8G2.2

354.8G9.2

(2) GPA

(2) 2001BLA/RAM

DfH0(R)ZK6.8G2.3 (K28.5G9.6)

(3) 85.7

358.7

(3) Derived

(3) 2004JAN/ROS

2-Chloroethyl hydroperoxide

90.1

377

Electrochemical

1996JON

2,2-Dichloroethyl hydroperoxide 91.5

383

Electrochemical

1996JON

384

Electrochemical

1996JON

CH3CHClOO–H DfH0(R)ZK13.1G0.8 (K54.7G3.4)

CH3CCl2OO–H DfH0(R)ZK15.2G2.3 (K63.8G9.6)

1,1,1-Trifluoro-2-chloroethyl

91.8

hydroperoxide CF3CHClOO–H

(continued)

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268

Comprehensive Handbook of Chemical Bond Energies

Table 6.1.1.3 (continued) O–H BDEs in ROOH BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) 1,1,2,2-Tetrachloroethyl

recommended data; reference in parentheses) kcal/mol 98.4

kJ/mol 411.6

Methods (reference in parentheses) Correlation

References 2004DEN/DEN

hydroperoxide CHCl2CCl2OO–H

Pentachloroethyl hydroperoxide (1) 91.5

383

(1) Electrochemical

(1) 1996JON

C2Cl5OO–H

(2) 98.7

413.1

(2) Correlation

(2) 2004DEN/DEN

iso-Propyl hydroperoxide iso-C3H7OO–H

(1) 85.1 (2) 84.9

356 355.1

(1) Electrochemical (2) Derived

(1) 1996JON (2) 2004JAN/ROS

DfH0(R)ZK15.6G2.7 (K65.4.G11.3)

Allyl hydroperoxide

(1) 89

372.4

(1) Photolysis

(1) 1981RUI/BAY

CH2aCHCH2OO–H

(2) 86.8

363

(2) Electrochemical

(2) 1996JON

tert-Butyl hydroperoxide

(1) 89.4

374

(1) VPPR

(1) 1983HEN/BEN

tert-C4H9OO–H

(2) 88.2

369

(2) Review

(2) 1997BEN/COH

DfH0(R)ZK24.3G2.2

(3) 85G2

355.6G8.4

(3) PES

(3) 1998CLI/WEN

(4) 84.2G2.1

352.3G8.8

(4) GPA

(4) 2001BLA/RAM

(5) 84.7

354.2

(5) Derived

(5) 2004JAN/ROS

RCH2OO–H

87.4

365.5

Correlation

2005DEN/TUM

R2CHOO–H

87.4

365.5

R3COO–H

85.7

358.6

88.4

369.8

Correlation

2004DEN/DEN(b)

DfH0(R)Z21.2 (88.7)

(K101.5.G9.2)

Alkyl hydroperoxides

2-Hydroperoxycyclohexan-1-one OO

H

O

7366—CHAPTER 6—5/2/2007—10:53—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

269

86.8

363

Electrochemical

1996JON

87.5

366

Electrochemical

1996JON

88.4

370

Electrochemical

1996JON

91.8

384

Electrochemical

1996JON

p-Cl

92.0

385

p-Me

91.5

383

Benzyl hydroperoxide C6H5CH2OO–H DfH0(R)Z27.4G1 (114.6G4.2)

p-NO2-benzyl hydroperoxide p-NO2-C6H4CH2OO–H

Diphenylmethyl hydroperoxide (C6H5)2CHOO–H

Phenyl hydroperoxide, substituted O

Y

O

H

YZH

p-OH

91.3

382

p-CN

92.1

385

p-Ph

93.2

390

92.0

385

Methaneperoxycarboxylic acid

(1) 92.3

386

(1) Electrochemical

(1) 1996JON

CH3C(O)OO–H

(2) 91.0

380.8

(2) Derived

(2) 2004JAN/ROS

96.5

403.9

Correlation

2004DEN/DEN

91.8

384

Electrochemical

1996JON

88.0

368

Electrochemical

1996JON

p

CO2K

DfH0(R)ZK36.9G1.4 (K154.4G5.8)

Benzeneperoxycarboxylic acid C6H5C(O)OO–H

2,2-Dichloro–2-hydroperoxyethane CCl2(CN)OO–H

Hydroperoxymethan-ol OHCH2OO–H

(continued)

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270

Comprehensive Handbook of Chemical Bond Energies

Table 6.1.1.3 (continued) O–H BDEs in ROOH BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) 2-Hydroperoxypropan-ol

reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

86.5

362

Electrochemical

1996JON

88.0

368

Electrochemical

1996JON

87.5

366

Electrochemical

1996JON

89.9

376

Electrochemical

1996JON

90.3

378

Electrochemical

1996JON

90.3

378

Electrochemical

1996JON

91.8

384

Electrochemical

1996JON

93.9

393

Electrochemical

1996JON

93.2

390

Electrochemical

1996JON

(CH3)2C(OH)OO–H

1-Hydroperoxyacetone CH3C(O)CH2OO–H

a-CO2K-methyl hydro - peroxide ðCO2KÞCH2 OO

H

2-Hydroperoxyethanenitrile (CN)CH2OO–H

a-CO2K-chloromethyl hydroperoxide ðCO2KÞCHClOO

H

a-CO2K-dichloromethyl hydroperoxide ðCO2KÞCCl2 OO

H

2,2-Dichloro-2hydroperoxyethanenitrile (CN)CCl2OO–H

Naphth-1-yl hydroperoxide 1-C10H7OO–H

Naphth-2-yl hydroperoxide 2-C10H7OO–H

7366—CHAPTER 6—5/2/2007—10:53—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

9-Anthracenyl hydroperoxide 9-C14H9OO–H

271

93.9

393

Electrochemical

1996JON

Correlation

2005DEN/TUM

Correlation

2005DEN/TUM

Correlation

2004DEN/DEN

Hydroperoxides RPhC(OH)OO–H

86.0

359.8

ROCH(R)OO–H

87.8

367.3

R3CC(O)OO–H

90.1

376.9

PhC(O)OO–H

96.5

403.8

RC(O)OO–H

92.5

387.1

RC(O)CH(R)OO–H

88.4

369.8

ROCH(Ph)OO–H

89.6

374.8

RC(O)OCH(Ph)OO–H

90.0

376.4

R2CHOC(R)2OO–H

85.7

358.4

87.9

367.6

90.1

376.9

88.4

369.8

86.5

362.1

Hydroperoxides

Cyclic hydroperoxides O

H

OO

O

O O

H

O O O

H

OO OH

H

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6.1.2

O–H bonds in oximes and hydrolamines

Table 6.1.2 O–H BDEs in Oximes and Hydrolamines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

83.4

348.9

Recommended

2004PRA/BLA

RZMe (E-isomer)

(1) 98.2 (2) 84.7

410.9 354.4

(1) AOP (2) Recommended

(1) 1992BOR/JI (2) 2004PRA/BLA

Me (Z-isomer)

(2) 82.6

345.6

CF3 (E-isomer)

(2) 84.4

353.1

CF3 (Z-isomer)

(2) 82.2

343.9

(1) AOP (2) Correlation (3) Recommended

(1) 1992BOR/JI (2) 2000DEN/DEN (3) 2004PRA/BLA

Oxime H2CaNO–H

Oximes H R

C

N

O

H

Et

(1) 98.1

410.5

CH3CO

(1) 89.6

374.9

PhCO

(1) 88.9

372.0

NH2

(1) 88.8

371.5

(1) 95.8 (2) 94.1 (3) 84.6

400.8 393.7 354.0

Oximes R1 R2

N

C

O

R1ZMe R2ZMe

H

Et

Et

(1) 92.3 (2) 90.6 (3) 83.8

386.2 379.1 350.6

iPr

rPr

(2) 86.0 (3) 82.7 (4) 87.7

359.8 346 366.9

Me

tBu

(4) 91.1

381.2

(4) AOP

(4) 1995BOR/ZHA(b)

iPr

tBu

(2) (3) (5) (6)

84.3 81.5 84.3 86.0

352.7 341.0 352.7 359.8

(5) EPR (6) AOP

(5) 1973MAH/MEN (6) 1996BOR/LIU

tBu

tBu

(2) (3) (4) (5) (6)

80.9 77.6 84.2 80.9 82.6

338.5 324.7 352.3 338.5 345.6

tBu

c-C5H9

(4) 90.7

379.5

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BDEs of O–X Bonds

Ph

Ph

PhCH2 PhCH2

273

(1) 89.0 (3) 81.6

372.4 341.4

(1) 89.1

372.8

Me

Et2NCH2

(1) 91.4

382.4

Me

NH2

(1) 86.7

362.8

Ph

NH2

(1) 86.9

363.6

cyclo-Hexanone, oximes cyclo-C5H10CaNO–H

(1) 90.3 (2) 88.6

377.8 370.7

(1) AOP (2) Correlation

(1) 1995BOR/ZHA(b) (2) 2000DEN/DEN

cyclo-Undercanane, oximes cyclo-C11H22CaNO–H

90.3

377.8

AOP

1992BOR/JI

(1) 80.0 (2) 81.7 (3) 77.2

334.7 341.8 323.0

(1) EPR (2) AOP (3) Recommended

(1) 1973MAH/MEN (2) 1995BOR/ZHA(b) (3) 2004PRA/BLA

Oximes, substituted (E)–(tBu)(1-Ad)CaNO–H AdZadamantyl (Z)–(tBu)(1-Ad)CaNO–H

(3) 76.9

321.7

(E)–PhCHaNO–H

(2) 90.2

377.4

(Z)–PhCHaNO–H

(3) 83.9 (2) 86.9 (3) 79.4

351.0 363.6 332.2

(E)–p-MeC6H4CHaNO–H

(2) 89.0

372.4

(Z)–p-MeC6H4CHaNO–H

(2) 86.5

361.9

(E)–p-MeOC6H4CHaNO–H

(2) 89.9

376.1

(Z)–p-MeOC6H4CHaNO–H

(2) 87.5

366.1

(E)–m-NO2–C6H4CHaNO–H

(2) 88.6

370.7

(Z)–m-NO2C6H4CHaNO–H

(2) 86.9

363.6

(E)–p-NO2C6H4CHaNO–H

(2) 88.0

368.2

(E)–PhCHCHCHaNO–H

(2) 88.6

370.7

(E)–CH3C(Ph)aNO–H

(2) 91.1 (2) 82.8

381.2 346.4

(Z)–CH3C(Ph)aNO–H

(2) 89.4 (2) 80.1

374.0 335.1

(E)–Me2NCH2C(CH3)aNO–H

(2) 92.0

384.9

(Z)–Me2NCH2C(Ph)aNO–H

(3) 88.5

370.3

(E)–(c-C4H8N)CH2C(Ph)aNO–H

(2) 88.6

370.7

(Z)–Me2NCH2C(Ph)aNO–H

(2) 87.6

366.5

(Z)–(c-C4H8N)CH2C(Ph)aNO–H

(2) 89.1

372.8

(E)–Me2NCH2CH2C(Ph)aNO–H

(2) 88.7

371.1

88.1

368.6

AOP

1995BOR/ZHA(b)

87.6

366.5

AOP

1995BOR/ZHA(b)

2-(Hydroxyimino)-1,7,7trimethylbicyclo(2.2.1)-heptane

NO

H

Norcamphor, oximes RaNO–H

(continued)

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Table 6.1.2 (continued) O–H BDEs in Oximes and Hydrolamines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Fluorene, oximes FlaNO–H

(1) 87.5 (2) 81.8

366.1 342.3

(1) AOP (2) Recommended

(1) 1992BOR/JI (2) 2004PRA/BLA

(Hydroxyimino)-2,7-dibromofluorenylmethane 2,7-BrFlaNO–H

89.6

374.9

AOP

1992BOR/JI

(Hydroxyimino)-2-PhSO2fluorenylmethane 2-PhSO2FlaNO–H

89.0

372.4

AOP

1992BOR/JI

AOP

1998BOR/ZHA

AOP

1998BOR/ZHA

(1) EPR

(1) 1981MAL/ING

Oximes, substituted CH

H

NO

Y

YZH

88.1

368.6

p-Cl

87.8

367.4

p-Br

87.6

366.5

p-MeO

87.8

367.4

p-Me

88.0

368.2

p-CF3

87.9

367.8

p-CN m-NO2 p-NO2

87.8 88.6 88.4

367.4 370.7 369.9

88.4

369.9

p-Cl

89.0

372.4

p-Br

89.0

372.4

p-Me

89.0

372.4

p-MeO

88.9

372.0

p-CF3

88.9

372.0

p-CN p-NO2

88.8 88.8

371.5 371.5

(1) 82.6G3

345.6G12.6

Oximes, substituted C(Me)

Y

NO

YZH

H

Hydroxylamines, substituted R R

RZCF3

NO

H

7366—CHAPTER 6—5/2/2007—10:55—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

275

(2) 85.3G3

356.9G12.6

(2) EPR

(2) 1984DOB/ING

Et

(3) (4) (5) (6)

290.8 317.6 304.3 291.2

(3) (4) (5) (6)

(3) 1978CAC/LIS (4) 1996BOR/LIU (5) 2000DEN/DEN (6) 2003REE/HAR

tBu

(4) 68.2 (7) !69.6

285.3 !291.2

(7) EPR

(7) 1973MAH/MEN

75.6

316.5

Correlation

2000DEN/DEN

76.1

318.6

(1) EPR (2) AOP

(1) 1990PER/BER (2) 1996BOR/LIU

(3) EPR

(3) 2002MIN/PUN

(1) AOP (2) EPR

(1) 1996BOR/LIU (2) 2003AMO/LUC

69.5 75.9 72.7 69.6G1.9

Kinetics AOP Correlation GPA

Hydroxylamines, substituted R

H

NO

tBu

RZiPrCH2C(O) PhCH2CH2C(O) CH3(CH2)9C(O)

75.8

317.2

C(O)CHCHPh

76.8

321.3

4-NO2C6H4 4-MeOC6H4C(O)

80.2 73.5

335.6 307.5

RZiPr

(1) 79.3 (2) 81.2

331.8 339.7

tBu

(1) 78.0 (2) 79.9

326.4 334.3

Ph

(2) 84.1 (3) 80 (1) 80.5

351.9 334.7 336.8

(2) 79.2G0.5

331.4G2.1

(1) 84.0 (1) 84.2

351.5 352.3

Hydroxamic acids, substituted H

O

R C

N Ph

O

3,5-(tBu)–C6H3

Hydroxamic acids, substituted Ph

O C

H

N

O

RZMe p-BrC6H4 p-CN–C6H4

R

(continued)

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Table 6.1.2 (continued) O–H BDEs in Oximes and Hydrolamines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Hydroxamic acids, substituted t Bu

H

O C

N

O

R

RZp-O2N–C6H4 p-MeO–C6H4 n-C10H21 N(CH2)5

80.2 75.9 75.8 74.4

335.6 317.6 317.1 311.3

EPR

1990PER/BER

Hydroxamic acids, substituted

80.2G0.5

355.6G2.1

EPR

2003AMO/LUC

RZPhCHaCH

76.8

321.3

EPR

1983JEN/PER

PhCH2CH2

76.2

318.8

CH3(CH2)9

75.8

317.1

(CH3)2CHCH2

75.6 74.4

316.3 311.3

EPR

1983JEN/PER

R

H

O C

N t Bu

O

RZ3,5-(NO3)2–C6H5

N-(tert-Butyl)-N-hydroxy-carboxamide, substituted O

t Bu N

RC

H

O

N

N-(tert-Butyl)-N-hydroxy-benzamide, substituted O Y

C

tBu N O

H

YZH

77.2

323.0

Ph

76.7

320.9

NO2

79.4

332.2

MeO

75.1

314.2

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BDEs of O–X Bonds

277

Hydroxy–N-piperidine, substituted O N

O N

C

H

74.4

311.1

Correlation

2000DEN/DEN

t Bu

Phenylamine, substituted 4-R-C6H4 4-R-C6H4

NO

H

RZMeO tert-Bu

(1) 71.8

300.4

(1) Correlation

(1) 2000DEN/DEN

(1) 70.9 (2) 68.2

296.5 285.3

(2) Kinetics

(2) 2005MAL/KOR

69.9 69.6

292.6 291.2

Correlation

2005DEN/TUM

Correlation

(1) 2000DEN/DEN

1-Hydroxy-pyrrolidine, substituted Me Me N X

O H

H Me Me

XZC(O)NH2 C(O)OH C(O)OMe

70.1

293.4

OH

68.7

287.3

2,5-Dihydropyrrole, substituted Me Me

H

N X

XZCl

O H

Me Me

(1) 70.0

292.7

Br

(1) 70.1

293.1

COMe

(1) 70.3

294.3

CONH2

(1) 70.1

293.1

C(O)OH

(1) 69.6

291.0

C(O)OMe

(1) 70.1 (2) 69.0

293.1 288.7

(1) 70.2

293.7

(2) 2005MAL/KOR

2,5-Dihydropyrrole, substituted Br

Me

Me N

X

XZBr

Me Me

O H

Correlation

(1) 2000DEN/DEN

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.1.2 (continued) O–H BDEs in Oximes and Hydrolamines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 68.4

286.2

(2) 2005MAL/KOR

C(O)OMe

(1) 70.1 (2) 68.6

293.4 287.0

COMe

(1) 70.4

294.5

(2) 69.5

290.8

Me

(2) 68.6 (3) 66.5

286.9 278.2

Ph

(2) 69.9 (3) 66.7

292.6 279.1

p-FC6H4

(2) 69.8 (3) 68.1

292.0 284.9

p-MeC6H4

(1) 71.9 (2) 69.5

300.8 290.7

OH

(3) 66.4

277.8

C(O)OH

(3a) 68.0

284.5

(3a) Correlation

(1) 71.4 (2) 71.9

298.7 300.8

Correlation

(1) 2000DEN/DEN (2) 2005MAL/KOR

Correlation

(1) 2000DEN/DEN

1-Hydroxy-tetrahydro-imidazole H

Z

Me Me N

N

Me

O H

Me Me

ZZH

(1) EPR (2) Correlation

(1) 1973MAH/MEN (2) 2000DEN/DEN

(3) Kinetics

(3) 2005MAL/KOR

1-Hydroxy-pyrrolidine, substituted Me Me N O

O H

Me Me

1-Hydroxy-tetrahydro-imidazole

Z

H

Me Me N

N Y

O

X Me

H

X Me

Y Z OH H

(1) 71.9

300.8

Me

H

PhC(O)CHa

(1) 71.4

298.7

Me

(2) 68.1

284.9

C6H13 Me

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(2) 2005MAL/KOR

BDEs of O–X Bonds

279

Hydroimidazole, substituted Me Me

X

N

N

O

Me Me

H

XZMe

(1) 70.6 (2) 69.8

295.2 292.0

Correlation

(1) 2000DEN/DEN (2) 2005MAL/KOR

iso-Pr

(1) 70.5

294.9

CCl3

(1) 71.0

296.9

Ph

(1) 70.3 (2) 69.2

294.2 289.5

p-FC6H4

(1) 70.8

296.1

p-ClC6H4

(1) 70.5

294.9

CH3C6H4

(1) 71.0

296.9

C(O)NH2

(1) 71.0

296.9

C(O)Me

(1) 71.0

296.9

CHaN–tert-Bu

(1) 70.5

294.8

CHaNOH

(1) 70.8

296.1

74.6

312.2

Correlation

2000DEN/DEN

71.0

297.1

Correlation

2000DEN/DEN

(1) 73.1 (2) 73.5

305.8 307.5

Correlation

(1) 2000DEN/DEN (2) 2005MAL/KOR

CHCl2

(1) 74.0

309.8

CH2Br

(1) 73.2

306.3

Hydroimidazole, substituted Me

Me Me

Me N

N

O H

Ph

Hydroimidazole, substituted Me Me Me Me

N

N O

O H

Ph

2,5-Dihydrioimidazole, substituted Me Me

Z

N O

Me Me

ZZMe

O H

(continued)

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Table 6.1.2 (continued) O–H BDEs in Oximes and Hydrolamines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CHBr2

(1) 74.4

311.1

BrCHCH3

(1) 73.1

305.8

C6H5

(1) 72.8 (2) 72.9

304.5 305.0

p-FC6H4

(1) 73.1

305.8

p-ClC6H4

(1) 73.2

306.3

p-BrC6H4

(1) 73.1

305.8

p-MeOC6H4

(1) 72.5

303.4

CN

(2) 76.5

320.1

74.0 74.1

309.8 310.0

Correlation

2000DEN/DEN

76.0 76.6

318.0 320.5

Correlation

2005MAL/KOR

77.0

322.2

AOP

1996BOR/LIU(b)

(1) 69.6 (2) 69.7

291.2 291.6

(1) EPR (2) AOP

(1) 1973MAH/MEN (2) 1996BOR/LIU

(3) 71.2

297.7

(3) Correlation

(3) 2000DEN/DEN

2,5-Dihydrioimidazole, substituted Me Me

Ph

N O

Y

O

Me

H

YZNHMe NMeOH

Methanesulphovinates, substituted Me Me

Me

+

N X

XZCH3 C6H5

N

MeSO4−

O H

Me Me

Piperidinol NO

H

Piperdin-1-ol, substituted H H Y

H Me Me N

H

YZH

H Me Me

O H

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BDEs of O–X Bonds

281

(4) 69.7

291.6

(4) Kinetics (4a) Correlation

Cl

(4a) 71.2

297.9

OH

(3) 72.2 (4a) 71.3

302.2 298.3

NH2

(4a) 71.0

297.1

Ph

(3) 70.7

295.9

PhC(O)O

(3) 71.2 (4a) 71.3

297.7 298.3

(4) 2005MAL/KOR

Piperdin-1-ol, substituted H Me Me

Y O

N X

O H

H Me Me

XZH YZH

67.5

282.4

Cl

H

74.4

311.3

Correlation

2005MAL/KOR

H

Br

72.6

303.8

(1) 71.8

300.4

(1) EPR

(1) 1973MAH/MEN

(2) Correlation

(2) 2005DEN/TUM

1-Hydroxy-piperidn-4-one, substituted Me Me

X

N

O

O H

Me Me

XZH Cl

(2) 73.6

307.9

Br

(2) 72.5

303.4

(1) 70.7 (2) 70.5 (3) 69.5

295.9 295.0 290.8

(1) Correlation (2) Correlation (3) Kinetics

(1) 2000DEN/DEN (2) 2005DEN/TUM (3) 2005MAL/KOR

73.8

308.8

Correlation

2000DEN/DEN

1-Hydroxy-1,2,5,6-tetra-hydropyridine, substituted Me

Me

N

O

H

Me

Ph

Me

1-Hydroxy-1,2,5,6-tetrahydropyrimidine, substituted Me Me Me

N O

N Me

O Me

H

(continued)

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282

Comprehensive Handbook of Chemical Bond Energies

Table 6.1.2 (continued) O–H BDEs in Oximes and Hydrolamines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

7-Aza-bicyclo(2.2.1)heptan-7-ol

N

O

H

(1) 77.0 (2) 78.0

322.2 326.4

(1) EPR (2) AOP

(1) 1973MAH/MEN (2) 1996BOR/LIU

76.2

318.8

EPR

1973MAH/MEN

72.7

304.3

Correlation

2000DEN/DEN

78.5G0.5

328.4G2.1

EPR

2003AMO/LUC

70.6G0.3

295.4G1.3

EPR

2003AMO/LUC

9-Azabi-cyclo(3.3.1)–nonane-9-ol O

N

H

Hydroxydiaza-cyclo-heptane, substituted

H

O

Me Me

N Me Me

NH

1-Hydroxyindolin-2-one, substituted

Me t Bu

Me O

N O

t Bu

H

1-Hydroxyindolin-3-one, substituted O Ph Ph

N O

H

7366—CHAPTER 6—5/2/2007—10:57—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

283

Indolinol, substituted Me t Bu

Me Ph

69.7G0.4

291.6G1.7

EPR

2003AMO/LUC

(1) (2) (3) (4)

O360 368.6G2.5 375G10 368.6G0.8

(1) (2) (3) (4)

(1) 2002MIN/PUN(b) (2) 2003AMO/LUC (3) 2003KOS/CAI (4) 2004ANN/GER

EPR

2004ANN/GER

EPR

2004ANN/GER

Ph

N O

t Bu

H

N-Hydroxyphthalimide (NHPI) O H N

O

O86 88.1G0.6 89.6G2.4 88.1G0.2

EPR EPR Polanyi plot EPR

O

N-Hydroxyphthalimide (NHPI), substituted H

R2

O

H O

N O

H

R2ZCH3

88.2G0.2

369.0G0.8

CH3O

87.3G0.2

365.3G0.8

CH3OCO

88.9G0.2

372.0G0.8

N-Hydroxyphthalimide (NHPI), substituted R1 H

O H N O

R3

R1ZF

O

88.6G0.2

370.7G0.8

CH3O

R3ZH H

87.9G0.2

367.8G0.2

CH3O

CH3O

87.1G0.2

364.4G0.8

(continued)

7366—CHAPTER 6—5/2/2007—10:57—JEBA—15362—XML MODEL B – pp. 255–368

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Comprehensive Handbook of Chemical Bond Energies

Table 6.1.2 (continued) O–H BDEs in Oximes and Hydrolamines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1,2-Dihydroquinoline, substituted H

O

Me

N

Me

X Me

XZC(CF3)2OH

(1) (2) (1) (2)

CPh3

70.5 69.6 69.2 65.0

294.9 291.2 289.5 272.0

(1) Correlation (2) Kinetics

(1) 2000DEN/DEN (2) 2005MAL/KOR

Correlation

(1) 2005DEN/TUM

Piperidinol, substituted H

O

Me

N

Me Ph3C

(1) 70.0

292.8

(2) 70.6

295.4

71.4G0.3

298.7G1.3

EPR

2003AMO/LUC

72.8G0.1

304.6G0.4

EPR

2003AMO/LUC

(2) 2005MAL/KOR

Me Ph

5,6-Dihydrophenanthridine, methanol, substituted Ph N

Ph

H O

3-Indol-3-ylindol-1-ol

Ph

NH

Ph

N O

H

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BDEs of O–X Bonds

285

Organomecury species

HgCl N

Me Me

70.9

296.6

75.3

315.1

Correlation

2005MAL/KOR

Me

N

Me

O

H

HgCl O N

Me Me

N O

Me Me H

6.1.3 O–H bonds in phenols Table 6.1.3 O–H BDEs in Phenols BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Phenol PhO–H DfH0(R)Z11.6G0.7 (48.5G2.9)

(1) 90.4G1, in sol. (2) 88.0G1.5 (3) 88.3G0.8 (4) 88.7G0.5 (5) 86.7G0.7, in gas

378.2G4.2 368.2G6.3 369.4G3.3 371.1G2.1 362.8G2.9

(1) AOP (2) Recommended (3) EPR (4) Recommended (5) Re-analysis

(1) 1996BOR/LIU (2) 1996TSA (3) 2003VAL/BRI (4) 2003GUE/COU (5) 2005MUL/KOR

Pentafluorophenol C6F5O–H

85.5

357.7

Correlation

2000DEN/DEN

(1) 91.2 (3) 87.4G0.5 (5) 84.5 (14) 87.2 (28) 87.4

381.6 365.7G2.1 353.5 365.0 365.6

(1) AOP

(1) 1990ARN/AMA

(2) AOP

(2) 1991BOR/CHE(b) (3) 1990LIN/SHE

(14) 89.1 (14) 86.3

372.7 361.0

(3) Pulse radiolysis (4) EPR (5) Electrochemical

Phenols, substituted

Y YZp-F

m-F o-F

O

H

(4) 1996LUC/PED (5) 1992PAR

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.1.3 (continued) O–H BDEs in Phenols BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(1) 93.4 (2) 90.3 (3) 87.6G0.5 (8) 91.1 (17) 90.9G2.5

390.8 378G2 366.5G2.1 381 380.1G10.6

(6) EPR

(6) 1973MAH/MEN

(7) PAC

(7) 2001SIL/MAT

(8) AOP

(8) 1997ZHU/ZHA

(2) 91.8 (14) 88.4 (15) 84.2G1 (17) 85.8G3.9

384.1 369.9 352.4G4.2 358.9G16.4

(9) AOP

(9) 1994ZHA/BOR

(10) Electrochemical

(10) 1991PAR/HAN

(2) 90.0 (14) 86.0 (15) 84.7G1 (16) 85.8 (17) 86.1G2.5

376.6 359.9 354.5G4.2 359.0 360.1G10.6

(11) EPR (12) AOP

(11) 1994LUC/PED (12) 1996BOR/LIU

(13) Electrochemical (14) Correlation

(13) 1975MAH/DAR (14) 2000DEN/DEN

(2) 90.7 (3) 88.1G0.5 (5) 85.2 (8) 91.3 (14) 89.0

379.5 368.6G2.1 356.5 382 372.3

(15) PAC

(15) 1998YAN/JIA

(16) Derived from DfH0 in ref.

(16) 2003BUR/KHA

o-Br

(14) 86.5

361.8 (17) Electroattach.

(17) 2003KHA/MUF

p-I

(3) 87.9G0.3 (5) 85.1 (28) 87.9

367.8G1.3 356.1 367.7

(18) EPR

(18) 2004LUC/PED

(24) TR–PAC

(24) 2004COR/GUF

(1) (2) (3) (4) (8)

364.8 371.1 360.2G2.1 369.0G2.5 374

(25) Derived

(25) 2005FAT/KAS

(26) Electrochemical

(26) 2005PRA/PES

(27) Combined

(27) 2005PIN/DIO

(28) Correlation

(28) 2005DEN/TUM

p-Cl

m-Cl

o-Cl

p-Br

p-Me

87.2 88.7 86.1G0.5 88.2G0.6 89.4

m-Me

(2) 89.4 (14) 87.6

374.0 366.7

o-Me

(2) 88.2 (12) 90.0 (14) 86.1

369.0 376.6 359.9

p-CN

(1) (2) (3) (5) (8)

389.5 394.1 388.7G2.9 377.0 397.0

m-CN

(2) 93.9 (14) 89.3

392.9 373.6

o-CN

(14) 88.0

368.1

p-NO2

(1) 93.8 (2) 94.7

392.5 396.2

93.1 94.2 92.9G0.7 90.1 94.9

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References

BDEs of O–X Bonds

287

(3) 94.2G1.4 (5) 91.3 (8) 95.4

394.1G5.9 382.0 399

m-NO2

(2) 94.3 (14) 87.7

394.6 366.9

o-NO2

(14) 86.9

363.4

p-MeO

(1) 86.3 (3) 82.6G0.5 (4) 82.8G0.2 (8) 85.1 (13) 84.0

361.1 345.6G2.1 346.4G0.8 356 351.5

m-MeO

(2) 90.2 (12) 90.8 (14) 88.4

377.4 379.9 369.8

o-MeO

(2) 86.0 (14) 84.2

359.8 352.1

p-OH

(2) 81.5 (3) 80.2 (8) 82.2 (13) 84.6 (14) 84.1

341.0 335.6 344 354.0 352.0

m-OH

(2) 90.9 (13) 90.9 (14) 88.2

380.3 380.3 369.1

o-OH

(14) 81.2 (18) 81.8 (24) 82.4

339.6 342.3 344.7

p-NH2

(2) 77.3 (3) 75.5 (8) 77.9 (14) 80.8

323.4 315.9 326 338.1

m-NH2

(2) 88.0 (8) 88.0 (14) 87.8

368.2 368 367.2

o-NH2

(14) 85.3

356.7

p-CF3

(2) 95.3 (8) 95.8 (14) 91.4

398.7 401.0 382.4

m-CF3

(2) 93.8 (14) 92.2

392.5 385.7

p-tBu

(2) 88.7 (4) 85.3G0.5 (8) 89.4 (13) 86.5 (14) 86.1

371.1 356.9G2.1 374 361.9 360.1

o-tBu

(14) 84.6

353.8

p-Ph

(2) 87.6 (8) 88.2 (13) 85.0 (14) 88.1 (28) 84.9

366.5 369 355.6 368.7 355.4

(continued)

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Table 6.1.3 (continued) O–H BDEs in Phenols

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

o-Ph

(14) 86.5

361.9

o-C2H3

(14) 85.8

358.9

p-CH2OH

(14) 85.7

358.7

o-C(O)OH

(27) 93.9G0.8

392.8G3.3

m-C(O)OH p-C(O)OH

(27) 91.7G0.9 (14) 88.8 (27) 90.8G0.8

383.6G3.8 371.7 380.0G3.4

p-MeCO2

(1) 88.9

372.0

m-EtCO2

(13) 89.9 (14) 90.7 (28) 89.8

376.1 379.4 375.7

p-Me2N

(2) 80.3 (3) 74.1 (8) 79.8 (14) 78.6

336.0 310.0 334 328.9

m-Me2N

(2) 87.9 (14) 86.2

367.8 360.6

p-MeSO2

(2) 95.0 (8) 95.6

397.5 400

m-MeSO2

(2) 92.3 (14) 90.7

386.2 379.5

p-MeCO

(2) 92.8 (3) 90.3G0.5 (5) 87.5 (8) 93.5 (14) 88.8

388.3 377.8G2.1 366.1 391.0 371.6

m-MeCO

(2) 91.8 (14) 90.0

384.1 376.5

o-MeCO

(14) 86.8

363.0

p-PhCO

(2) 92.5 (8) 93.2 (14) 90.8

387.0 390 379.9

o-Imidazolyl

(26) 83.6G3.7

349.8G15.5

m-Imidazolyl

(26) 89.0G1.7

372.4G7.1

p-Imidazolyl

(26) 85.3G2.0

356.9G8.4

p-COOK

(3) 89.9G0.5 (5) 87.1 (28) 89.9

376.1 364.4 376.1

o-(CH2)3CHO

(14) 86.9

363.6

p-n-BuO

(14) 83.1

347.8

p-NHPh

(28) 81.1

339.3

o-O%

(25) 65.4G3.6 (25) 67.5G3.7

273.6G15.1 282.4G15.5

m-O%

(25) 90.0G3.6

376.6G15.1

p-O%

(25) 60.4G1.7

252.7G7.1

Methods (reference in parentheses)

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References

BDEs of O–X Bonds

289

(25) 58.8G2.7

246.0G11.3

(25) 79.3G4.8 (25) 80.9G4.0

331.8G20.1 338.5G16.7

m-OK

(25) 63.0G3.7

263.6G15.5

p-OK

(2) 73.0 (3) 72.4 (25) 63.0G3.7 (25) 61.4G2.3 (28) 53.3 (28) 62.0

305.4 302.9 263.6G15.5 256.9G9.6 223.0 259.5

3,5-Cl2

(2) 93.9 (14) 92.3

392.9 386.2

2,5-Cl2

(15) 85.0G1

355.7G4.2

3,5-Me2

(2) 89.1 (8) 88.2 (12) 89.7 (14) 87.2 (16) 86.6G0.4

372.8 369 375.3 364.7 362.5G1.5

2,3-Me2

(14) 85.0

355.5

2,4-Me2

(14) 86.2

360.5

2,6-Me2

(2) 85.1 (4) 84.5G0.4 (13) 85.1 (14) 84.8 (17) 82.7G0.2 (14) 84.8 (22) 86.5

356.1 353.5G1.7 356.1 354.6 346.1G0.8 354.6 361.9

2-Me-4-tBu

(14) 86.0

359.9

2-tBu-4-Me

(14) 86.2

360.5

(2) 82.1 (4) 82.8G0.2 (8) 82.7 (13) 85.1 (14) 82.8

343.5 346.4G0.8 346 356.1 346.4

2,4-tBu2

(14) 85.9

359.5

3,5-tBu2

(4) 86.6G0.3 (7) 90.3G0.5 (13) 86.9 (14) 86.6

362.3G1.2 378.0G2.0 363.6 362.4

2,2-(OH)2

(24) 78.6

328.9

3,5-(OH)2

(24) 88.8

371.4

2,6-(MeO)2

(4) 83.2G0.2 (28) 83.7 (4) 86.7G0.3

347.9 350.0 362.8

o-O

K

p-NKPh

Phenols, di-substituted

3,4-Me2

2,6-tBu2 (Also see Table 6.1.4)

3,5-(MeO)2

(2) AOP

(2) 1991BOR/CHE(b)

(4) EPR

(4) 1996LUC/PED

(7) PAC

(7) 2001SIL/MAT

(8) AOP

(8) 1997ZHU/ZHA

(12) AOP

(12) 1996BOR/LIU

(13) Electrochemical

(13) 1975MAH/DAR

(14) Correlation

(14) 2000DEN/DEN

(15) PAC

(15) 1998YAN/JIA

(16) EPR (17) EPR (22) Electrochemical (24) TR–PAC

(16) (17) (22) (24)

2003LUC/MUG(b) 2003VAL/BRI 2004GRA/LAN 2004COR/GUF

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.1.3 (continued) O–H BDEs in Phenols

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(28) 86.7

362.6

2-OH-4-tBu

(14) 81.8

342.4

2-Me-4-OH

(14) 83.6

349.8

2-tBu-4-MeO

(14) 82.1

343.4

(2) 93.1 (14) 91.4

389.5 382.4

2,4,6-Cl3

(15) 83.7G1 (20) 85.8

350.3G4.2 359

2,4,5-Me3

(14) 85.3

2,4,6-Me3 (see next cell)

(see next cell)

2,4,6-tBu3 (Also see table 6.1.4)

Phenols, tri-substituted 3,4,5-Cl3

Methods (reference in parentheses)

References

(2) AOP

(2) 1991BOR/CHE(b)

(4) EPR (6) EPR

(4) 1996LUC/PED (6) 1973MAH/MEN

356.8

(8) AOP

(8) 1997ZHU/ZHA

(see next cell)

(9) AOP (11) EPR

(9) 1994ZHA/BOR (11) 1994LUC/PED

(6) 81.2 (8) 82.2 (9) 82.6 (11) 81.2G0.1 (18) 81.3

339.7 344 345.6 339.7G0.4 340.2

(14) Correlation

(14) 2000DEN/DEN

(15) PAC

(15) 1998YAN/JIA

(16) EPR

(16) 2002LUC/MUG

2,4-tBu2-6-Me

(14) 85.1

355.9

(17) EPR

(17) 1988COR/COL

2,6-Me2-4-Cl

(14) 84.0

351.4 (18) EPR

(18) 2000PED/COR

3,5-Me2-4-CH2C(O)OH

(14) 83.7

350.3

2,6-Me2-4-CN

(14) 84.6

354.0

(20) Derived from DfH0 in ref.

(20) 2003BUR/KHA

2,6-Me2-4-NH2CH2

(14) 83.2

348.1

(21) EPR

(21) 2003VAL/BRI

(25) 86.7G0.8

362.9G3.2

(22) Electrochemical (23) EPR

(22) 2004GRA/LAN (23) 1997PED/LUC

(15) 79.3G0.3 (16) 80.7G0.3

331.8 337.6

(25) EPR

(25) 1998PAU/COR

2,5-t-Bu-4-OH 3,5-tBu-2-OH

(22) 70.6 (14) 81.3 (22) 84.0

295.4 340.3 351.3

2-OH-3,6-tBu2

(14) 81.1

339.5

2,3-MeO-4-OH

(14) 82.2

343.8

2,3-Me2-4-MeO

(14) 79.2

331.4

2,4,6-(MeO)3

(23) 80.0G0.1 (see next two cells) (14) 83.1

334.7G0.5

347.5

(14) 83.8

350.6

(21) 81.0G0.1

339.0G0.5

2-Me-4-tBu-6-R RZS-(3-Me-4-OH-5-tBuPh) 1,3-tBu2-5-OH

2-S(CH2)2CN-4-Me-6MePhCH 2-Me-4-NH2CH2-6-tBu 2,6-tBu2K4-Me

7366—CHAPTER 6—5/2/2007—11:00—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

291

3,6-tBu2-4-Me

(7) 80.5G0.9 (11) 80.7G0.3

336.8 337.6

2-tBu-4,6-Me2

(14) 85.0

355.8

2,5-t-Pentyl-4-OH

(16) 80.8G0.2

338.1G0.8

4-C3H7K2,5-di-OH (propyl gallate)

(16) 82.6G0.3

345.6G1.3

4-C8H17-2,5-di-OH (octyl gallate)

(16) 82.5G0.3

345.2G1.3

in sol. (1) 89.2

in gas 87.3

in sol. 373.2

in gas 365.3 (1) PAC

(1) 1995WAY/LUS

tBu tBu tBu (Also see table 6.14)

(2) 83.2

81.2

348.1

339.7 (2) Calorimetry

(2) 1969MAH/FER

tBu

Me

tBu

(3) 81.6 (4) 82.7 (5) 79.7

79.6 80.7

341.4 346.0 333.5

333.0 (3) PAC 337.6 (4) EPR (5) EPR

(3) 1996WAY/LUS (4) 1994LUC/PED (5) 2000PED/COR

Me

Me

Me

(1) 83.8 81.8 (6) 82.7 (22) 82.1

350.6 346.0 343.4

342.3

Phenols, substituted

R2 R4

O

R2 H

R4 H

H

R6

R6 H

(6) ERP (22) Electrochemical

Me

MeO

Me

(3) 79.2 (4) 79.6

77.2 77.6

331.4 333.0

323.0 324.7

tBu

t-Bu

H

(3) 84.1

82.1

351.9

343.5

in sol. (1) 89.2

in gas 86.2

in sol. 373.2

in gas PAC 360.7

(6) 2002AMO/FER (22) 2004GRA/LAN

Phenols, substituted

Y YZH

O

H

2-MeO

(1) 88.6

86.6

370.7

362.3

2,6-(MeO)2

(1) 81.9

79.7

342.7

333.5

2,4-(MeO)2

(1) 83.5

81.5

349.4

341.0

2,4,6-(MeO)3

(1) 78.9 76.9 330.1 (also see first two cells) (2) 83.8 81.4 350.6

321.7

4-MeO

340.6

(1) 1999HEE/KOR

(2) 1996WAY/LUS

Phenols, tetra-substituted R5 R4

R3

O H

R1 R2 R1ZR4ZR5ZMe R2ZH, R3ZMeO

(1) 79.2G0.2

331.4G0.8

(1) EPR

(1) 1996LUC/PED

(continued)

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292

Comprehensive Handbook of Chemical Bond Energies

Table 6.1.3 (continued) O–H BDEs in Phenols BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(3) EPR

(3) 2002LUC/MUG

(4) Correlation

(4) 2000DEN/DEN

342.7 326.4 342.4

(1) EPR (2) EPR (3) Correlation

(1) 1996LUC/PED (2) 1991COR/COL (3) 2005DEN/TUM

(4) 81.4 (5) 81.8

340.5 342.3

(4) Correlation (5) EPR

(4) 2000DEN/DEN (5) 2002AMO/FER

(1) Electrochemical

(1) 2002JON/LIN

(2) Electrochemical (3) Pulse radiolysis

(2) 1975MAH/DAR (3) 2001DAS

TR–PAC

2004COR/SAN

R1ZR2ZR4ZR5ZMe R3ZH

(4) 83.1

347.8

R1ZR2ZR3ZR5ZMe R4ZH

(4) 83.9

351.2

R2ZR5ZH, R3ZOH R1ZR4ZCMe2Et

(3) 80.8G0.2

338.1G0.8

R1ZR5ZOH, R2ZR4ZH R3ZC(O)OC3H7

(3) 82.6G0.3

345.6G1.3

R1ZR5ZOH, R2ZR4ZH R3ZC(O)OC8H17

(3) 82.5G0.3

345.2G1.3

R1ZR2ZR4ZMe R3ZOH, R5ZH

(4) 82.4

344.7

(1) 81.9G0.2 (2) 78.0G0.1 (3) 81.8

Phenols, penta-substituted

R4

R5

R3

O

H R1 R2 R1ZR2ZR4ZR5ZMe R3ZMeO R1ZR2ZR3ZR4ZR5ZMe

Biphenols

O

Y

H

(Y') YZ2-OH

Y 0 Z2-OH

(1) 88.9

372

2-OK

2-OH

(1) 92.0

385

4-OH

4-OH

(1) 83.4 (2) 85.2 (3) 85.5

349 356.5 357.7

(1) 78.9

330

4-OK

4-OH

4-Hydroxy-diphenylmethanes

H O RZC6H5 C6H4-4-OH

CH2

R 85.1

356.2

85.7

358.4

7366—CHAPTER 6—5/2/2007—11:01—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

293

3-Pyridinol

H

O

N

3-Pyridinols, substituted CH3 N H N O N CH3

CH3 N

N

CH3

H

O

N CH3

397.5

AOP

1993BOR/SIN

78.2G0.3

327.2G1.3

EPR

2003WIJ/PRA

77.0G0.5

322.2G2.1

76.3G0.6

319.2G2.5

75.4G0.7

315.5G2.9

(1) 91.1 (2) 90.3

381.2 377.8

Est. by exp.

(1) 2001PRA/DIL (2) 2003VAL/BRI

EPR

(1) 2001PRA/DIL

N

N CH3

H

O

95

H

O

N

5-Pyrimidinol

N

H

O

Y N YZH

5-Pyrimidinols, substituted

N

H

O

Y N

YZ2-CH3, 6-CH3, 4-CH3

(1) 85.20G0.50

356.48G2.09

2-tBu, 6-tBu, 4-CH3

(1) 84.10G0.25

351.87G1.05

2-CH3, 6-CH3, 4-N(CH3)2

(1) 78.16G0.25

327.02G1.05

2-CH3, 6-CH3, 4-CH3O

(2) 82.48G0.50

345.10G2.09

2-tBu, 6-tBu, 4-N(CH3)2

(2) 76.64G0.10

320.66G0.42

(1) 78.3G0.2 (2) 78.2

327.6G0.8 327.2

(2) 2003VAL/BRI

Chroman-6-ol, substituted

Me O H Me

O

Me Me

(1) EPR (2) Correlation

(1) 1996LUC/PED (2) 2005DEN/TUM

Me

(continued)

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Table 6.1.3 (continued) O–H BDEs in Phenols BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

a-Tocopherol H

R5

O CH2

O

R7

R

CH3

(1) 78.9 (2) 78.9 (3) 80.9G1, in sol. (4) 79.3, in sol. (4) 77.3, in gas (5) 78.23G0.25

330.1 330.1 338.5G4.2 331.8 323.4 327.31G1.05

(4) 82.2, in sol. (4) 80.2, in gas (6) 81.9

343.9 335.6 342.8

b-Tocopherol R5ZCH3, R7ZH

(6) 80.2

335.6

g-Tocopherol R5ZH, R7ZCH3

(6) 80.1

335.1

78.1G0.3

CH3

R = CH2CH2CHCH2 H 3 CH3

R5ZR7ZCH3 (vitamin E) d-Tocopherol R5ZR7ZH

(1) (2) (3) (4)

EPR EPR AOP PAC

(1) (2) (3) (4)

1992JAC/HOS 1994LUC/PED 1996BOR/LIU 1996WAY/LUS

(5) EPR

(5) 2003VAL/BRI

(6) Correlation

(6) 2000DEN/DEN

326.8G1.3

EPR

2006SHA/AMO

79.1 78.0 78.6

330.8 326.4 328.9

Correlation

2000DEN/DEN

78.7

329.1

79.7

329.3

80.0

334.7

78.8

329.7

78.5 79.1

328.4 331.0

All–rac-a-selenotocopherol H

CH3

O CH3

CH2

Se

R

CH3

CH3

R = CH2CH2CHCH2 H 3 CH3

chroman, substituted H

O

65 78

4 3 12

O

Y

YZ5,7,8-trimethyl 2,4,5,7-tetramethyl 2,5,7,8-tetramethyl-2COOH 2,5,7,8-tetramethyl-2CH2CH2C(O)COOH 2,5,7,8-tetramethyl-2CH2COOH 2,5,7,8-tetramethyl-2CH3O 2,5,7,8-tetramethyl-2CH2CH2C(O)OCH3 2,2,5,7,8-pentamethyl 2,5,7,8-tetramethyl-2CH2OH

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BDEs of O–X Bonds

295

2H-chromene, substituted 2,2,5,7,8-pentamethyl H

O

4

6

1

79.2

331.5

Correlation

2000DEN/DEN

82.3

344.3

Correlation

2000DEN/DEN

82.3

344.3

Correlation

2000DEN/DEN

O

Ubiquinol-2 H

O

CH3O

CH 3 R

CH 3O O

H

R = (CH 2CHC(CH 3)CH 2) 2H

Ubiquinol-6 O CH 3O

CH 3 R

CH3O

O

H R = (CH 2CHC(CH 3)CH 2) 6H

Ubiquinol-10 H

O

CH 3O

CH 3

CH3O

R O

in sol. 80.5

in gas 78.5

in sol. 336.8

in gas 328.4 PAC

1999HEE/KOR

H R = (CH 2CHC(CH 3)CH 2) 10H

5,7-Dimethyl-tocol, DMT RO–H

79.7

333.5

Correlation

2000DEN/DEN

YZ2,2,6,7-tetramethyl

78.8

329.7

Correlation

2000DEN/DEN

2,4,6,7-tetramethyl

78.0

326.4

Dihydrobenzofuran, substituted 7 6 5 4

H

O

12 3

Y

O

(continued)

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Table 6.1.3 (continued) O–H BDEs in Phenols BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

2,4,6,7-tetramethyl2-C(O)OH

79.8

334.0

2,2,4,6,7-pentamethyl

77.9

326.0

Methods (reference in parentheses)

References

2,3-dihydrobenzo(b)furan-5ol and its 1-thio, 1-seleno, and 1-telluro analogues O

H

X

XZO

81.3

340

S

80.5

337

Se Te

80.3 80.5

336 337

Electrochemical

2001MAL/JON

Correlation

2000DEN/DEN

(1) Electrochemical (2) AOP (3) Correlation

(1) 1975MAH/DAR (2) 1991BOR/CHE(b) (3) 2000DEN/DEN

Correlation

2005DEN/TUM

Tetrahydroquinoline, substituted Y H

O

NH

8 7 6 5

1 2 3 4

YZ5,7,8-trimethyl-N-acetyl

83.7

350.3

79.6

332.9

(1) 84.5 (2) 84.0 (3) 82.1

353.5 351.5 343.4

(1) 86.5 (2) 88.0 (3) 84.6

361.9 368.2 353.8

1 site with 5-OH

(1) 83.6

349.8

2 site with 6-Br

(2) 88.5

370.3

79.7

333.5

5,7,8-trimethyl-N-ethyl

Hydroxynaphthalene, substituted 7 6

8

1

5

4

2 3

O

H

H–O bond at 1 site DfH0(R)Z39.5 (165.3) 2 site DfH0(R)Z41.6 (174.1)

Naphthalene-1,4-diol O

H

OH

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BDEs of O–X Bonds

297

2,4-Dichlorophenoxy-1 0 ,5 0 dichloro-phenyl-6, 2 0 -ether Cl Cl

O Cl

O Cl

81.3

340

Derived from DfH0 in ref.

2003BUR/KHA

H

0

DfH (R)ZK30.6G6 (128G25)

Hydroxyfluorene 8 7 6 5

9

1 2 O 4 3

H

H–O bond at 1 site

(1) 82.0

343.1

(1) Electrochemical

(1) 1975MAH/DAR

3 site

(2) 80.9

338.3

(2) Correlation

(2) 2000DEN/DEN

H–O bond at 1 site

84.8

354.7

Correlation

2000DEN/DEN

2 site

87.7

367.0

3 site

86.6

362.5

4 site

85.1

356.2

(1) 80.2

335.6

(1) Electrochem.

(1) 1975MAH/DAR

3 site with 8-OH (1) 79.0 (2) 75.5

330.5 315.9

(2) Correlation

(2) 2000DEN/DEN

3 site with 10-OH (1) 79.2 (2) 75.9

331.4 317.7

Hydroxy-phenanthrene

H

O 32

4 1

56 7 8 10

9

Pyrene, substituted 9 8 7 6

1

10

5

2 3 O

H

4

H–O bond at 3 site

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Comprehensive Handbook of Chemical Bond Energies

6.1.4

O–H bonds in sterically hindered phenols

Table 6.1.4 O–H BDEs in Sterically Hindered Phenols

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) Phenols, substituted

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 82.1 (4) 82.8G0.2 (8) 82.7 (13) 85.1 (14) 82.8

343.5 346.4G0.8 346 356.1 346.4

(2) AOP (4) EPR (8) AOP (13) Electrochem. (14) Correlation

(2) 1991BOR/CHE(b) (4) 1996LUC/PED (8) 1997ZHU/ZHA (13) 1975MAH/DAR (14) 2000DEN/DEN

(14) 82.3 (15) 82.4

344.5 344.8

(2) AOP

(2) 1991BOR/CHE(b)

(4) EPR

(4) 1996LUC/PED

p-NC

(14) 84.2

352.4 (6) EPR

(6) 1973MAN/MEN

p-HS

(14) 81.3

340.0 (7) PAC

(7) 2001SIL/MAT

p-Me

(4) 81.0 (7) 80.5G0.9 (8) 80.1 (17) 79.9G0.2 (18) 79.9G0.1

338.9 336.9G3.6 335 334.3G0.8 334.4G0.5

(8) AOP

(8) 1997ZHU/ZHA

(9) AOP

(9) 1994ZHA/BOR

(10) Electrochem.

(10) 1991PAR/HAN

p-Et

(8) 80.1

335 (11) EPR

(11) 1994LUC/PED

p-NO

(14) 82.7

346.0 (14) Correlation

(14) 2000DEN/DEN

p-NO2

(8) 86.3 (10) 86.7 (14) 85.6 (15) 84.9

361 362.8 358.0 355.2

(15) EPR

(15) 2002BRI/LUC

(16) EPR

(16) 1994LUC/PED

p-NH2

(14) 80.0

334.6

(17) EPR

(17) 1988COR/COL

p-NH2CH2

(14) 77.2

322.9

(18) EPR

(18) 2000PED/COR

p-CN

(15) 84.2 (20) 85.3

352.4 356.9

(19) EPR

(19) 2003LUC/MUG

(20) Correlation

(20) 2005DEN/TUM

p-OH

(19) 78.6

328.9

t Bu O

H

t Bu

Phenols, substituted t Bu O

Y

H

t Bu

YZp-Cl

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BDEs of O–X Bonds

299

p-MeO

(4) 78.3 (8) 79.6 (9) 79.7 (11) 77.6G0.4 (20) 77.8

327.6 333 333.5 324.7G1.3 325.5

p-MeC(O)NH

(14) 78.1

326.7

p-HO(O)CCH2

(14) 80.5

336.9

p-MeC(O)CH2

(14) 81.9

342.8

p-CNCH2

(14) 74.4

311.1

p-MeC(O)

(14) 83.1

347.8

p-HC(O)

(14) 83.1 (15) 84.2

347.8 352.3

p-HO(O)C

(14) 83.4 (15) 84.3

348.8 352.7

p-MeOC(O)

(8) 82.7 (9) 84.3 (15) 84.1

346 352.7 351.9

p-tBuOC(O)

(14) 83.1

347.8

p-tBu

(6) 81.2 (8) 82.2 (9) 82.6 (11) 81.2G0.1 (18) 81.3

339.7 344 345.6 339.7G0.4 334.0

p-tBuO

(14) 79.2 (20) 78.9

331.3 330.2

p-BuS

(14) 81.5

341.0

p-RS

(16) 81.0

338.9

p-Ph

(14) 80.7 (15) 81.2 (20) 80.8

337.7 339.7 337.9

p-PhO

(14) 80.6

337.2

p-PhS

(14) 82.8

346.4

p-PhCH2

(14) 81.2 (20) 80.1

339.7 335.1

p-PhCHZCH

(15) 78.9

330.1

p-Ph2CH

(14) 81.8

342.3

p-(CH2)2Ph

(14) 81.3

340.0

p-(CH2)2tBu

(14) 81.2

339.8

p-C18H37OC(O)CH2CH2 (octadecyloxyoxo2 0 -ethyl) p-C18H37O (octadecyloxy) p-C24H49O (tetracozyloxy)

(14) 81.2

339.8

(14) 78.5

328.6

(14) 78.7

329.2

(continued)

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Table 6.1.4 (continued) O–H BDEs in Sterically Hindered Phenols BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Phenols, substituted Ph O

H

Y

YZp-MeO

Ph

(20) 78.6

328.7

p-NH2

(20) 77.3

323.6

p-CH2CN

(20) 74.6

312.0

p-Ph

(8) 84.8 (9) 85.3

354.8 356.9

(8) AOP (9) AOP

(8) 1997ZHU/ZHA (9) 1994ZHA/BOR

p-HO(O)CCH2

(20) 78.1

326.6

(20) Correlation

(20) DEN/TUM

81.3

340.0

Correlation

2000DEN/DEN

82.1

343.3

Correlation

2005DEN/TUM

81.1

339.4

Correlation

2005DEN/TUM

Phenols, substituted R O

O Ph

R R=

O

H

Ph

Phenols, substituted t Bu H

t Bu

O

OH t Bu

t Bu

Ethane, substituted, O–H bond H t Bu

O

OH

t Bu

CH2 CH2 t Bu

t Bu

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BDEs of O–X Bonds

301

Methane, substituted O–H bond H

O

1

23 4 6 5

5 6 4 1 3 2

CH2

OH

2,4-tBu2

(1) 81.5 (2) 81.1G0.1

340.9 339.3G0.4

3,5-tBu2

(1) 81.4

340.5

81.2G0.2

Ethane, substituted O–H bond Me

OH

O

t Bu

(1) Correlation (2) EPR

(1) 2005DEN/TUM (2) 2003AMO/LUC

339.7G0.8

EPR

2003AMO/LUC

81.5

340.9

Correlation

2000DEN/DEN

82.4

344.9

Correlation

2000DEN/DEN

81.0

339.0

Correlation

2000DEN/DEN

H t Bu

t Bu

t Bu

Methane, substituted O–H bond, CR4 H

O R=

t Bu

t Bu

CH2CH2C(O)OCH2

Benzene, substituted O–H bond R R t Bu

R R

=

CH2

O

H

t Bu

Ether, substituted O–H bond, R–O–R H

O R=

Ph

Ph

(CH2)2C(O)O(CH2)2

(continued)

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Table 6.1.4 (continued) O–H BDEs in Sterically Hindered Phenols BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) Indophenol, substituted t Bu

O

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

t Bu

N

78.2

327.1

Correlation

2000DEN/DEN

81.5

341.0

Correlation

2000DEN/DEN

81.3

340.1

Correlation

2000DEN/DEN

81.2

339.8

Correlation

2000DEN/DEN

80.3

335.9

Correlation

2005DEN/TUM

80.1

335.3

O

H t Bu

t Bu

Silane, substituted O–H bond, SiR4

R= H

t Bu CH2CH2O

O

t Bu

Sulfide, substituted CHMePh H O

S

CH2Ph

Me

Sulfide, substituted O–H bond, RCH2SCH2R t Bu

H

R=

O t Bu

Sulfide, substituted CHMePh O

H

Me

Sx

xZ1 2

Me

HO

CHMePh

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BDEs of O–X Bonds

303

Sulfide, substituted

CHMePh

H

O

X Me

XZS(CH2)4CN

82.5

345.2

SCH2CH3

81.1

339.4

Correlation

2005DEN/TUM

S-n-Bu

81.1

339.2

SCH2Ph

81.0

338.7

81.4

340.7

81.5

341.1

Correlation

2005DEN/TUN

(1) 81.0G0.4 (2) 80.8

338.9G1.3 338.0

(1) EPR (2) Correlation

(1) 1994LUC/PED (2) 2005DEN/TUM

(1) 78.8G0.3 (2) 78.7 (2) 78.4

329.7G12.6 329.3 328.3

(1) EPR (2) Correlation

(1) 1994LUC/PED (2) 2005DEN/TUM

Sulfide, substituted CHMePh XS

O H CHMePh

XZH Me

4-((4-Hydroxyphenylthio)methylthio)phenyl, substituted t Bu HO

t Bu

Me SCS

t Bu

O

Me

H

t Bu

4-((4-Hydrophenyl)methylene)cyclohexa-2,5dien-1-one, substituted t Bu O

t Bu CH

O H

t Bu

t Bu

(continued)

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Table 6.1.4 (continued) O–H BDEs in Sterically Hindered Phenols BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Galvinol t Bu

H

CH

O

78.7

329.1

Correlation

2000DEN/DEN

EPR

2004AMO/LUC

O

t Bu

trans-Hydroxystilbene substituted OMe R1 H

OMe

O R2

R1ZH R2ZOH

79.3

331.8

tBu

tBu

78.6

328.9

tBu

OH

77.7

325.1

80.4

336.4

EPR

2004AMO/LUC

81.6

341.6

Correlation

2005DEN/TUM

81.7

341.7

Correlation

2005DEN/TUM

cis-Hydroxystilbene substituted

t Bu H

OMe O

t Bu OMe

Silicoorganics

t-Bu H

O

Si

O

4

t-Bu

Methane, substituted O C

(CH2)2

t-Bu H

O O t-Bu

4

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BDEs of O–X Bonds

305

Ether, substituted O

(CH2)3

t-Bu

O(CH2)2

O

O

H 2

81.2

339.6

Correlation

2005DEN/TUM

82.9

347.0

Correlation

2005DEN/TUM

82.6

345.6

Correlation

2005DEN/TUM

81.1

339.3

Correlation

2004VAR

62.0

259.5

Correlation

2004VAR

t-Bu

Phone, substituted t-Bu

t-Bu HO

O

t-Bu

t-Bu

H

O

Phone, substituted OH t-Bu

t-Bu

t-Bu t-Bu HO

O t-Bu

H

t-Bu

4-Hydroxydiphenylamine NH

O

H

4-Hydroxydiphenylaminyl radical N

O

H

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Comprehensive Handbook of Chemical Bond Energies

O–H bonds in metal-containing species

Table 6.1.5 O–H BDEs in Metal-Containing Species BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0w, kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Permanganic anion [H–OMnVIO3]K

(1) 83 (2) 80G3

347.3 334.7G12.6

Electrochemical

(1) 1995COO/MAY (2) 1997GAR/KUE

H–OCr(O)Cl2

w83

w347

Electrochemical

1995COO/MAY

H–ORuVZO

82.8

346.4

Est. by exp.

2003YIU/LEE

84G2

351.5G8

Electrochemical

2003BRY/MAY

82G2

343.1G8

Manganese-oxo cubane complex Mn4O3(O–H)(O2PPh2)6

(1) O94.4 (2) O94

O395 O393.3

Electrochemical

(1) 2003CAR/BOU (2) 2003MAN/WOL

Antion [Mn(H2O)5(HO–H)]2K

90

376.6

Electrochemical

2003GUP/BOR

[L2MnII(m-O–H)2MnIIIL2](PF6)3

75

313.8

Electrochemical

1997WAN/MAY

[L2MnIII(m-O)(m-O–H)MnIVL2](PF6)3 LZ1,10-phenanthroline

79

330.5

76

318.0

Electrochemical

1996BAL/PEC

Z3,5-di(Cl)salpn

77

322.2

Z3,5-di(NO2)salpn

79

330.5

Z2,2-bipyridyl

84

351.5

85 89 82

355.6 372.4 343.1

Electrochemical

1997CAU/PEC

H–O bonds [(bpy)2(py)RuIVO]2C–H IV

2C

[(bpy)2(py)Ru (OH)]

–H

[MnIIIMnIV (m-O)(m-O–H)(L)2] LZsalpnZN,N 0 -bis(salicylidene) K1,3-propanediamine

MnIII2L2(HO–H) LZ2-hydroy-1,3-bis(3,5-X2salicylidenamino)propane XZ3,5-H 3,5-Cl 3,5-t-Bu

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BDEs of O–X Bonds

307

[MnIIIMnIVL2(HO–H)]C LZ2-hydroy-1,3-bis(3,5-X2salicylidenamino)propane XZ3,5-H 3,5-Cl 3,5-t-Bu

89 94 86

372.4 393.3 359.8

Electrochemical

1997CAU/PEC

82G2

343.1G8.4

Electrochemical

2005GOL/COL

K2[MnIIH31(O–H)]

77

322.2

Electrochemical

2003GUP/BOR

K[MnIIIH31(O–H)]

110

460.2

K2[FeIIH31(O–H)]

66

276.1

K[Fe H31(O–H)]

115

481.2

Cation [FeII(H2O)5(HO–H)]2C

77

322.2

Electrochemical

2002GOL/JON

½FeII ðPY5ÞðMeO–HÞ ðCF3 SO3 Þ2 PY5Z2,6-bis((2-pyridyl)methyomethane)pyridine

84

351.5

Electrochemical

1997JON/STA

LiO–H NaO–H

128.2 119.4

536.4 499.6

Derived from DfH0 in ref.

1996NIST

Derived from DfH0 in ref.

1996NIST

Monocuclear manganese hydroxide MnII(PY5)(HO–H) PY5Z2,6-bis(bis(2-pyridyl)methoxymethane)-pyridine

O–H bond in M–O complex, K salts

N

1 = O

NH

O H

O

H HN

N N

M N

O

N

III

KO–H

124.7

521.7

CsO–H

129.1

540.2

BeO–H MgO–H

112.1 105.4

469 441

CaO–H

108.9

456

(continued)

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Table 6.1.5 (continued) O–H BDEs in Metal-Containing Species BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0w, kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

SrO–H

98.0

410

BaO–H

76.6

320

BO–H AlO–H

99.5 111.1

416 465

Derived from DfH0 in ref.

1996NIST

GaO–H InO–H

121.5 116.7G5

508 488G21

Derived from DfH0 in ref.

1996GUR/VEY

TlO–H

118.2G7

495G30

Derived

This volume

CrO–H

83.5G3.5

349.4G14.6

MnO–H

83.5G10

349G42

FeO–H

(1) 80.9G4

338G17

(1) Derived from DfH0 in ref

(1) 2003SCH/SCH

(2) 83.4G4.7

348.9G19.7

(2) Derived

(2) This volume

118

494

Derived from DfH0 in ref.

1996NIST

B(O)O–H

6.1.6

O–H bonds in radicals

Table 6.1.6 O–H BDEs in Radicals

The broken bonds (boldfaceZdissociated atom) DfH0w, kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Hydroxyl radical H–O%

102.75G0.07

429.91G0.29

Recommended

2002RUS/WAG

Hydroperoxy radical % H–OO

(1) 48.2G0.8

201.7G3.3

(1) 2001IUPC

(2) 48.3G1.2

202.1G5.0

(1) Derived from DfH0 in ref. (2) GIB MS

7366—CHAPTER 6—5/2/2007—11:05—JEBA—15362—XML MODEL B – pp. 255–368

(2) 1990FIS/ARM(b)

BDEs of O–X Bonds

309

H–OC%H2 H–O-C%H–CH3

30.2G0.2 24.6G1

126.4G0.8 102.9G4

Derived from DfH0 in ref.

1986PED/NAY

D–OC%H2

30.5G1.6

127.4G6.8

PD

2004FEN/DEM

H–O-C%H–CH3

23

96

Derived

2005LIU/GRO

H–O-C%Cl–CH3 H–O-C%H–CH2CH3

19.6G3 26.4G1.5

82.0G12.6 110.5G6.3

Derived from DfH0 in ref.

1996NIST

H–OC%(CH3)2

30.1G2.0

125.9G8.4

%

H–OC H(C6H5)

30.7G2

128.4G8.4

H–OC%(C6H5)2

27.6G1.7

115.5G7.1

H–O(O)C%

4.6G0.7

19.2G2.9

Derived

This volume

62.0

259.5

Correlation

2004VAR

4-Hydroxydiphenylaminyl radical N

6.2

O

H

O–O bonds

Table 6.2 O–O BDEs

The broken bonds (boldfaceZdissociated or atom group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Oxygen O–O

(1) 119.11G0.04 (2) 118.876G0.003

498.36G0.17 497.375G0.013

(1) Spectroscopy (2) TIPPS

(1) 1979HUB/HER (2) 1997MAR/HEP

Oxygen cation O–OC (also see Chapter 26)

(1) 154.5 (2) 154.82G0.07

646.6 647.75G0.17

(1) Derived (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

Oxygen anion O–OK (also see Chapter 26)

94.6G0.1

395.9G0.6

UV PES

2003ERV/ANU

(continued)

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Table 6.2 (continued) O–O BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated or atom group) Ozone O–O2

kcal/mol (1) 25.5

kJ/mol 106.6

(2) 24.27G0.06, 0 K 101.53G0.25 (3) 24.49G0.01, 0 K 102.48G0.04

Methods (reference in parentheses)

References

(1) Derived from DfH0 in ref. (2) PHOFEX (3) LIF

(1) 1998CHA (2) 1997TAK/KIS (3) 1999TAN/TAK

Hydroperoxy radical O–OH

(1) 65.6G0.8 (2) 65.55G0.08

274.5G3.3 274.26G0.33

Derived

(1) 1998LIT/RUS (2) 2006RUS/PIN

Hydroperoxide HO–OH

(1) (2) (3) (4)

213.4G4.2 220G5 214.6G0.4 210.66G0.42

(1) Review (2) Photolysis (3) Derived (4) Derived from DfH0 in ref. (5) PAC

(1) (2) (3) (4)

51G1 52.6G1.2 51.3G0.1 50.35G0.10, in gas (5) 46.8G1.4, in aq.

195.8G5.9

1982MCM/GOL 1988DIX/NIG 1998LIT/RUS 1998CHA

(5) 2004AUT/BRO

Fluoride hydroperoxide HO–OF

45.6G2

199.7G8.4

Derived from DfH0 in ref.

1998COL/GRE

Bromine hydroperoxide HO–OBr

33.1G2

138.5G8.4

Derived from DfH0 in ref.

1998COL/GRE

Difluoroperoxide FO–OF

47.7

199.6

Derived from DfH0 in ref.

1994FRE/KAB

Dioxygen fluoride radical O–OF

110.7

463.1

MS

1966MAL/MCG

Dioxygen bromide radical O–OBr

52.3

219.0

Derived

2000XIE/SCH

Dichloroperoxide ClO–OCl

(1) 16.5G0.7 (2) 17.3G0.7

69G3 72.5G3

(1) UV photo. (2) UV photo.

(1) 1979BAS/HUN (2) 1988COX/HAY

7366—CHAPTER 6—5/2/2007—11:06—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

311

(3) 18.1G0.7 (4) 17.3G0.7 (5) 16.6G1.1

75.7G3 72.4G2.8 69.4G4.6

(3) UV photo. (4) PIMS (5) UV photo.

(3) 1994NIC/FRI (4) 2005PLE/KUH (5) 2006BRO/ZAB

Chloroperoxide HO–OCl

w35

w146

Est. by exp.

1996BOG/THO

Dichlorine trioxide

(1) 14.8G2.9

62G12

UV photolysis

(1) 1989HAY/COX

ClO–OClO

(2) 11.1G1.2

46.4G5

Bromoperoxide HO–OBr

w35

w146

Est. by exp.

1996BOG/THO

Diiodoperoxide IO–OI

17.9G4

74.9G17

Derived from DfH0 in ref.

2003NASA/JPL

trans-Perp-peronitrous acid HO–ONO

(1) (2) (3) (4) (5)

71.1 83G1 76.6 %70.3 %67.8G0.4

(1) Review (2) Kinetics (3) Derived (4) Spectroscopy (5) Photolysis

(1) (2) (3) (4) (5)

cis-cis-Peronitrous acid HO–ONO

19.9G0.5, 0 K

83.3G2.1

LIF

2005MAT/SIN

Peroxynitric acid HO–ONO2

39G2

163.2G8.4

Derived

1978BAL/GOL

Methyl hydroperoxide HO–OCH3

(1) 45.2G1

189.1G4.2

(1) 1996NIST

(2) 47.4G1.5

198.3G6.3

(3) w42.6G1, at 0 K w178.2G4

(1) Derived from DfH0 in ref. (2) Derived from DfH0 in ref. (3) LIF

K24.6

Derived

This volume

Hydroperoxy methyl HO–OCH2

17 19.8G0.2 18.3 %16.8 %16.2G0.1

K102.9

(2) 1993BUR/MAU

2000GOL/SMI 2002HIP/NAS 2002DIX/FEL 2003POL/KON 2005KON/POL

(2) 2001DOR/NOV (3) 2005MAT/SIN(b)

(continued)

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Table 6.2 (continued) O–O BDEs

The broken bonds (boldfaceZdissociated or atom group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Trifluoromethyl hydroperoxide HO–OCF3

48.1G5

201.3G20.9

Derived from DfH0 in ref.

2003NASA/JPL

Ethyl hydroperoxide HO–OC2H5

42.7G1.5

178.7G6.3

Derived from DfH0 in ref.

1996NIST

iso-Propyl hydroperoxide HO–O-iso-C3H7

44.4G1.5

185.8G6.3

Derived from DfH0 in ref.

1996NIST

tert-Butyl hydroperoxide HO–O-tert-C4H9

(1) 44.8G0.5 (2) 44.5G1

187.4G2.1 186.2G4.2

(1) Pyrolysis (2) Derived from DfH0 in ref.

(1) 1992SAH/RIG (2) 1996NIST

1-Hydroperoxy-2,2dimethylpropane HO–OCH2C(CH3)3

46.3G1.9

193.7G7.9

Pyrolysis

1974BAT/CHR

Alkyl hydroperoxide HO–OR

44–46

184–192

Review

2000REI/PRA

Zeroane HO–OC(O)H

47.6G2

199.2G8.4

Derived from DfH0 in ref.

2003FEL/DIX

Methaneperoxycarboxylic acid 40.6G0.5 HO–OC(O)CH3

169.9G2.1

Pyrolysis

1992SAH/RIG

Ethaneperoxycarboxylic acid HO–OC(O)C2H5

40.6G0.5

169.9G2.1

Pyrolysis

1992SAH/RIG

Dimethyl peroxide CH3O–OCH3

(1) 37.6G2 (2) 40.0G1.5

157.3G8.4 167.4G6.3

(1) Pyrolysis (2) Derived from DfH0 in ref.

(1) 1974BAT/CHR (2) 1996NIST

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BDEs of O–X Bonds

313

(3) 42.8G2

179.1G8.4

(3) 2001DOR/NOV

151.4G0.4

(3) Derived from DfH0 in ref. (4) Re-analyzed

(4) 36.2G0.1

Ditrifluoromethyl peroxide CF3O–OCF3

(1) (2) (3) (4) (5)

40.6G5 46.7G0.8 46.2G1 47.5G0.5 45.2G0.8

170G21 195.4G3.3 193.3G4.2 198.7G2.1 189.1G3.5

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Diethyl peroxide C2H5O–OC2H5

(1) 38.7G1 (2) 39.7G1.3

161.9G4.2 166.1

(1) 1974BAT/CHR (2) 1996NIST

(3) 36.1G0.7

150.9G2.7

(1) Pyrolysis (2) Derived from DfH0 in ref. (3) Re-analyzed

Dipropyl peroxide nC3H7O–OnC3H7

(1) 37.1G1 (2) 35.8

155.2G4.2 149.6

(1) Pyrolysis (2) Re-analyzed

(1) 1974BAT/CHR (2) 2004TUM/DEN(b)

di-iso-Propyl peroxide iso-C3H7O–O-iso-C3H7

(1) 37.7 (2) 36.9G0.2

157.7 154.2G0.9

(1) Pyrolysis (2) Re-analyzed

(1) 1974BAT/CHR (2) 2004TUM/DEN(b)

Dibutyl peroxide n-C4H9O–O-n-C4H9

36.4

152.4

Re-analyzed

2004TUM/DEN(b)

Disec-butyl peroxide sec-C4H9O–O-sec-C4H9

(1) 36.4G1 (2) 36.4

152.3G4.2 152.3

(1) Pyrolysis (2) Re-analyzed

(1) 1983BAT (2) 2004TUM/DEN(b)

Ditert-butyl peroxide tert-BuO–O-tert-Bu

(1) 38.0G1 (2) 38.2G0.5 (3) 41.0G1.4

159.0G4.2 159.8G2.1 171.5G5.9

(1) 1983BAT (2) 1992SAH/RIG (3) 1996NIST

(4) 38.9G0.5 (5) 37.5G2.4

162.8G2.1 156.7G9.9

(1) Pyrolysis (2) Pyrolysis (3) Derived from DfH0 in ref. (4) VLPP (5) PAC

(4) 2000REI/PRA (5) 2001SAN/MUR

tert-Butyl-tert-amyl peroxide tert-BuO–O-tert-Am

39.3

164.4

Derived

1980ISL

Dineopentyl peroxide tert-BuCH2O–OCH2-tert-Bu

(1) 36.4G1 (2) 34.2

152.3 143.2

(1) Pyrolysis (2) Re-analyzed

(1) 1977TRE/WRI (2) 2004TUM/DEN(b)

Derived Derived Pyrolysis VLPP Re-analyzed

(4) 2004TUM/DEN(b)

1972LEV/KEN 1972KEN/LEV 1976DES/FOR 2000REI/PRA 2004TUM/DEN(b)

(3) 2004TUM/DEN(b)

(continued)

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Table 6.2 (continued) O–O BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated or atom group)

kJ/mol

Methods (reference in parentheses)

References

(1) 39.3G1 (2) 35.5

164.4G4.2 148.7

(1) VLPP (2) Re-analyzed

(1) 1973PER/GOL (2) 2004TUM/DEN(b)

33.7

140.8

Re-analyzed

2004TUM/DEN(b)

di-1,1-Diethylethyl peroxide MeC(Et)2O–OC(Et)2Me

35.5

148.4

Re-analyzed

2004TUM/DEN(b)

Di-tert-nonafluorobutyl peroxide (CF3)3CO–OC(CF3)3

35.5G1.1

148.5G4.6

Pyrolysis

1977IRE/GOR

Re-analyzed

2004TUM/DEN(b)

di-1,1-Dimethylpropyl peroxide EtC(Me)2O–OC(Me)2Et

di-1,1-Di-tert-butyl-propyl peroxide t-BuC(Me)2O–OC(Me)2tBu

kcal/mol

Dialkyl peroxide Me3CO–OR RZCMe2Et

35.8

149.7

CMe2Pr

36.8

154.2

C(Me)2CHMe2

35.6

148.8

CMe2CH2Cl

35.9

150.0

CMe2CMe3

35.2

147.4

CMe2Ph

35.9

150.0

CMe2CH2Ph

35.9

150.3

35.8

149.6

Re-analyzed

2004TUM/DEN(b)

35.7

149.2

Re-analyzed

2004TUM/DEN(b)

139.5G1.4

Re-analyzed

2004TUM/DEN(b)

Peroxide, substituted

O O

OtC(CH3)3

Peroxide, substituted

O

OtC(CH3)3

di-1,1-Dimethylbenzyl peroxide 33.3G0.3 PhC(Me)2O–OC(Me)2Ph

7366—CHAPTER 6—5/2/2007—11:07—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

Hexaphenyl peroxide Ph3CO–OCPh3

315

31.4

131.4

Electrochemical

2004DON/WOR

35.7 35.8 35.7 36.1

149.3 149.8 149.6 151.0

Re-analyzed

2004TUM/DEN(b)

37.2

155.6

Pyrolysis

1978CZA/SCH

20.6G3

86.2G12.6

Laser photolysis

2001TUC/BAD

di(Sulfur pentafluoro) trioxide 30.3 SF5O–OOSF5

126.8

Pyrolysis

1981CZA/SCH

tert-Butyl 1,1-dimethyl-1silaethyl peroxide (CH3)3CO–OSi(CH3)3

47

196.6

Pyrolysis

1978MAR/COM

2,2-Diethyl-2-germabutyl tert- 46 butyl peroxide tert-BuO–OGeEt3

192.5

Pyrolysis

1964SKI

2,2-Diethyl-2-stannabutyl tert- 46 butyl peroxide tert-BuO–OSnEt3

192.5

Pyrolysis

1961HER

HOOO radical HO–OO

(1) 1.8G2

7.5G8.4

(1) This volume

(2) 4–7

17–29

(1) Derived from DfH0 in ref. (2) LP

(2) 2005SMI/ROB

42.0

175.6

Derived

2000XIE/SCH

Peroxides, substituted

O Y

CH3 YZp-CH3O m-CH3O p-Cl p-NO2

OtC(CH3)3

CH3

di(Sulfur pentafluoro) peroxide SF5O–OSF5

Sulfur peroxide FC(O)O–OS(O2)F

Trioxygen bromide radical O–OOBr

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.2 (continued) O–O BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated or atom group)

kcal/mol

kJ/mol

ROOO radical CH3O–OO

K3G3

12.6G12.6

C2H5O–OO

K2G3

K8.4G12.6

Trifluoromethoxy-trifluoromethyl peroxide CF3OO–OCF3

30.3G2

Chlorofluorotrioxide FClOO–O

Methods (reference in parentheses)

References

Derived from DfH0 in ref.

This volume

126.8G8.4

Pyrolysis

1981CZA/SCH

58.4

244.3

Review

1970ONE/BEN

Chlorotrioxide ClO–OO

7.7!

32.2!

Derived from DfH0 in ref.

2003NASA/JPL

Tetrahydrofuran-2-yl-peroxy C4H7O–OO

32

133.9

PAC

2000KRA/CIR

Dioxan-2-yl-peroxy C4H7O2–OO

34

142.3

PAC

2000KRA/CIR

Bifluoroformyloxy FC(O)O–OC(O)F

23

96.2

Pyrolysis

2003MAX/BUR

Peroxyacetyl nitrate CH3C(O)O–ONO2

31.4G2

131.4G8.4

Derived from DfH0 in ref.

2003NASA/JPL

Perfluorinated peroxide CF3OC(O)O–OCF3

34.0G0.7

142.3G2.9

FT-IR

2005PAC/ARG

7366—CHAPTER 6—5/2/2007—11:07—JEBA—15362—XML MODEL B – pp. 255–368

BDEs of O–X Bonds

Diacetyl peroxide CH3C(O)O–OC(O)CH3

317

(1) 30.4G2 (2) 36 (3) 33.5G5

127.2G8.4 150.6 140.2G21

(1) 1975REE/BRA (2) 1998COL/GRE (3) 2001DOR/NOV

126.2G0.5

(1) Photodetach. (2) Derived (3) Derived from DfH0 in ref. (4) Correlation

(4) 30.2G0.1

Bis(trifluoroacetyl) peroxide CF3C(O)O–OC(O)CF3

30

125.5

Kinetics

2001KOP/WIL

Perfluorinated peroxide CF3OC(O)O–OC(O)F

29G1

121.3G4.2

FT-IR

2005PAC/ARG

Bis(trifluoromethyl) peroxydicarbonate CF3OC(O)O–OC(O)OCF3

28.5

119.2

Pyrolysis

2003MAX/BUR

Propanoyloxy propanoate C2H5C(O)O–OC(O)C2H5

(1) 30.4G2 (2) 36 (3) 30.1G0.2

127.2G8.4 150.6 126.0G1.0

(1) Photodetach. (2) Derived (3) Correlation

(1) 1975REE/BRA (2) 1998COL/GRE (3) 2005TUM/DEN

Butanoyloxy butanoate nC3H7C(O)O–OC(O)nC3H7

(1) 30.4G2 (2) 36 (3) 29.9G0.2

127.2G8.4 150.6 125.1G0.9

(1) Photodetach. (2) Derived (3) Correlation

(1) 1975REE/BRA (2) 1998COL/GRE (3) 2005TUM/DEN

2-Methylpropanoyloxy 2methylpropanoate iC3H7C(O)O–OC(O)iC3H7

26.8

112.2

Correlation

2005TUM/DEN

Pentanoyloxy pentanoate nC4H9C(O)O–OC(O)nC4H9

29.6

124.0

Correlation

2005TUM/DEN

Correlation

2005TUM/DEN

Acyl peroxides RC(O)O–OC(O)R RZnC5H11

30.0

125.4

nC6H13

29.8G0.2

124.8G0.7

nC7H15

30.0G0.3

125.4G1.1

nC8H17

29.7G0.2

124.2G0.8

nC9H19

29.8

124.5

nC11H23

29.9G0.2

125.2G1.0

nC13H27

30.9

129.2

(4) 2005TUM/DEN

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.2 (continued) O–O BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated or atom group)

kcal/mol

kJ/mol

nC15H31

29.6

123.7

nC17H35

29.7

124.3

30.9G0.5

129.1G1.9

29.6

123.7

28.4

118.8

27.4

114.8

27.5

115.0

30.6

127.9

30.3

126.8

30.3

126.9

C6H5

30.8G0.3

128.9G1.1

o-CH3–C6H4

28.8

120.7

m-CH3–C6H4

30.7G0.3

128.6G1.3

p-CH3–C6H4

30.4G0.2

127.4G0.8

o-Cl–C6H4

29.5

123.6

m-Cl–C6H4

30.9G0.5

129.3G1.9

p-Cl–C6H4

30.7

128.4

o-Br–C6H4

29.3

122.5

m-Br–C6H4

31.2

130.6

p-Br–C6H4

30.9

129.4

o-CH3O–C6H4 m-CH3O–C6H4 p-CH3O–C6H4 m-NO2–C6H4 p-NO2–C6H4 p-t-C4H9–C6H4 PhCH2

28.3 30.4 30.0G0.3 30.7 30.6 30.6 30.5

118.5 127.1 125.4G1.3 128.5 128.0 127.9 127.5

Acyl peroxides RC(O)O–OC(O)R RZ

Methods (reference in parentheses)

Correlation

7366—CHAPTER 6—5/2/2007—11:08—JEBA—15362—XML MODEL B – pp. 255–368

References

2005TUM/DEN

BDEs of O–X Bonds

Acyl peroxides RC(O)O–OC(O)CH3 RZnC3H7

319

30.7

128.6

nC4H9

30.4

127.1

nC5H11

30.5

127.5

nC6H13

30.3

126.6

28.5

Acyl peroxides nC3H7C(O)O–OC(O)C2H5

Acyl peroxides RC(O)O–OC(O)CH3 RZcyclo-C6H11

Correlation

2005TUM/DEN

119.4

Correlation

2005TUM/DEN

Correlation

2005TUM/DEN

Correlation

2005TUM/DEN

30.3

126.7

C6H5

30.3

126.6

2,4,6-Trimethyl-C6H2

29.3

122.4

o-Cl–C6H4

30.2

126.3

m-Cl–C6H4

29.5

123.4

o-Br–C6H4

30.0

125.4

m-Br–C6H4

29.5

123.6

p-Br–C6H4

29.2

122.1

m-CH3–C6H4

30.5

127.8

p-CH3–C6H4

30.5

127.8

p-CH3O–C6H4

30.3

126.6

m-NO2–C6H4

32.6

136.2

Acyl peroxides RC(O)O–OC(O)Ph RZCH2Cl

30.6

128

C2H5

31.0

129.5

C3H7

31.0

129.5

CH2CH(CH3)2

31.0

129.7

nC7H15

30.4

127.3

Peroxydisulfuryl difluoride FS(O)2O–OS(O)2F

22–24

92–100

ESR

1969NUT/VIN

Peroxodiphosphate [O3PO–OPO3]4K

18.4G4.3

77G18

PAC

2003MES/BIL

Peroxodisulfate [O3SO–OSO3]2K

28.7G2.6

120G11

PAC

2000BRU/CHU

(continued)

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Table 6.2 (continued) O–O BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated or atom group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ascaeidole O

O

DPA–O2 (endoperoxide, 9,10diphenyl-9,10-epidioxynthracene) OO Ph

28.5

119.2

Electrochemical

2004DON/WOR

16.3

68.2

Electrochemical

2004DON/WOR

23.2

97.1

Electrochemical

2004DON/WOR

!108.8

Electrochemical

1991MER/LIN

96.2–100.4

Electrochemical

1998DON/WOR

Ph DMA–O2 (endoperoxide, 9,10dimethyl-9,10epidioxynthracene) OO CH3

CH3

Flavins, substituted R10

CH3

N

CH3

N

O

N

10

1 4a 3

5

R5

N

O O

R3 !26

O

R

Artemisinin

CH3

O

O

O O

O

23–24

CH3 CH3

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BDEs of O–X Bonds

6.3

321

O–C bonds

6.3.1

O–C bonds in alcohols

Table 6.3.1 O–C BDEs in Alcohols

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Trifluoromethanol HO–CF3

%115.2G0.3

%482.0G1.3

PIMS

1997ASH/APP

Trifluoromethylhypofluorite FO–CF3

97.5G4

408G17

Derived from DfH0 in ref.

1996NIST

Methanol HO–CH3

(1) 92.2G0.2

385.8G0.8

(1) 1986PED/NAY

(2) 92.8 (3) 92.00G0.17

388.3 384.93G0.71

(1) Derived from DfH0 in ref. (2) Derived (3) Recommended

Ethynol HO–CbCH

134.6

563.2

Derived from DfH0 in ref.

1996NIST

Ethenol HO–C2H3

111.1

464.8

Derived from DfH0 in ref.

1996NIST

Ethanol HO–C2H5

93.5G0.7

391.2G2.9

Derived from DfH0 in ref.

1986PED/NAY

2,2,2-Trifluoroethanol HO–CH2CF3

97.6G2

408.4G8.4

Derived from DfH0 in ref.

2002CRC

Allyl alcohol HO–CH2CHaCH2

79.5G1

332.6G4.2

Derived from DfH0 in ref.

1986PED/NAY

2-Propen-1-ol HO–CHaCHCH3

102.5G1.5

428.9G6.3

Derived from DfH0 in ref.

1994PED

(2) 2001MIR/KOS (3) 2002RUS/WAG

(continued)

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Table 6.3.1 (continued) O–C BDEs in Alcohols

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1-Propanol HO–nC3H7

93.7G0.7

392.0G2.9

Derived from DfH0 in ref.

1986PED/NAY

2-Propanol HO–iso-C3H7

95.1G1

397.9G4.2

Derived from DfH0 in ref.

1986PED/NAY

1-Butanol HO–nC4H9

93.2G1

389.9G4.2

Derived from DfH0 in ref.

1986PED/NAY

2-Butanol HO–sec-C4H9

94.7G1

396.1G4.2

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-1-propanol HO–iso-C4H9

94.2G1

394.1G4.2

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-2-propanol HO–tert-C4H9

95.2G1

398.3G4.2

Derived from DfH0 in ref.

1986PED/NAY

1-Pentanol HO–nC5H11

92.3G1.5

386.2G6.3

Derived from DfH0 in ref.

2002CRC

2-Pentanol HO–CH(CH3)(nC3H7)

95.2G1

398.3G4.2

Derived from DfH0 in ref.

2002CRC

3-Pentanol HO–CH(C2H5)2

95.4G1

399.2G4.2

Derived from DfH0 in ref.

2002CRC

2-Methyl-2-butanol HO–C(CH3)2(C2H5)

94.6G1.5

395.8G6.3

Derived from DfH0 in ref.

2002CRC

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BDEs of O–X Bonds

323

1-Hexanol HO–C6H13

92.4G2

386.6G8.4

Derived from DfH0 in ref.

2002CRC

2-Hexanol HO–C6H13

95.6G1.5

400.0G6.3

Derived from DfH0 in ref.

2002CRC

Phenol HO–C6H5

110.8G1.0

463.6G4.2

Derived from DfH0 in ref.

1986PED/NAY

Pentafluorophenol HO–C6F5

(1) 107 (2) 106.8G2.2

447.7 446.9G9.2

(1) Derived (2) Derived from DfH0 in ref.

(1) 1975CHO/GOL (2) 1996NIST

Benzyl alcohol HO–CH2C6H5

(1) 81.2 (2) 79.9G0.6

339.7 334.1G2.6

(1) VLPP (2) Derived from DfH0 in ref.

(1) 1979ROS/GOL (2) 2004VER/TAT

a, a-Dimethylbenzyl alcohol HO–C(CH3)2C6H5

81.1G1.5

339.3G6.3

Derived from DfH0 in ref.

1999VER

cyclo-Pentanol cyclo-C5H9–OH

92.2G1.5

385.8G6.3

Derived from DfH0 in ref.

1986PED/NAY

69.8

292

Derived from DfH0 in ref.

2003BUR/KHA

95.3G1.5

398.7G6.3

Derived from DfH0 in ref.

1986PED/NAY

(1) 92.0

384.9

(1) 1988LIA/BAR

(2) 91.6

383.3

(1) Derived from DfH0 in ref. (2) Derived

1-Hydroxy-1,3,4-trichloro cyclo-pentadiene Cl OH

Cl

Cl

cyclo-Hexanol cyclo-C6H11–OH

Adamantanol

OH 12 1-OH

(2) 2002MIR/LEB

(continued)

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Table 6.3.1 (continued) O–C BDEs in Alcohols

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(3) 94.6

395.8

(1) 98.0

410.0

1-Naphthol 1-C10H7–OH

112.0G1.5

2-Naphthol 2-C10H7–OH

Dimethylaminomethanol (CH3)2(NH2)C–OH

Methods (reference in parentheses)

References

(3) Derived from DfH0 in ref.

(3) 2002MIR/LEB

468.6G6.3

Derived from DfH0 in ref.

1986PED/NAY

111.8G1.5

467.8G6.3

Derived from DfH0 in ref.

1986PED/NAY

74.2G1.5

310.4G6.3

Derived from DfH0 in ref.

1986PED/NAY

2-OH

95.4G1

399.2G4.2

Derived from DfH0 in ref.

1986PED/NAY

3-OH 4-OH

112.8G2 112.2G2

472.0G8.4 469.4G8.4

Polyols HOCH2–OH

(1) 98.3

411.3

(1) Derived from DfH0 in ref.

(1) 1969BEN/CRU

CH3CH(OH)–OH

(1) 98.7

413.0

HOCH2CH2–OH

(2) 81.0

338.9

(2) Derived

(2) 2001MIR/KOS

2-OH

Pyridinol, HO–pyridinyl

HO

4

5 6 1N 3 2

(HOCH2)2CH–OH

(2) 80.2

335.6

HOCH2CH(OH)CH2–OH

(2) 79.6

333.0

(HOCH2)3CCH2–OH

(2) 80.2

335.6

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BDEs of O–X Bonds

6.3.2

325

O–C bonds in ethers

Table 6.3.2 O–C BDEs in Ethers

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parantheses)

References

Dimethyl ether CH3–OCH3

84.1G1.0

351.9G4.2

Derived from DfH0 in ref.

1986PED/NAY

Iodomethyl methyl ether ICH2–OCH3

89.2G3

373.2G12.6

Derived from DfH0 in ref.

1996NIST

Ethyl methyl ether CH3–OC2H5

83.6G1.0

349.8G4.2

Derived from DfH0 in ref.

1986PED/NAY

Ethyl methyl ether CH3O–C2H5

84.9G1.3

355.2G5.4

Derived from DfH0 in ref.

1986PED/NAY

2-Chloroethyl methyl ether CH3O–CHClCH3

88.5G2

370.3G8.4

Derived from DfH0 in ref.

1996NIST

Divinyl ether C2H3–OC2H3

(1) 64.1G1.2 (2) 78.1G2.5

268G5 326.8G10.5

(1) PA (2) Derived from DfH0 in ref.

(1) 2001BOU/ROO (2) 2002CRC

Ethyl vinyl ether C2H3–OC2H5

102.1G1.5

427.2G6.3

Derived from DfH0 in ref.

1986PED/NAY

Ethyl vinyl ether C2H5–OC2H3

65.2G2.5

272.8G10.5

Derived from DfH0 in ref.

2002CRC

2-Chloroethyl vinyl ether CH2ClCH2–OC2H3

66.0G2.5

276.1G10.5

Derived from DfH0 in ref.

2002CRC

Diethyl ether C2H5–OC2H5

85.4G1.5

357.3G6.3

Derived from DfH0 in ref.

1986PED/NAY

(continued)

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Table 6.3.2 (continued) O–C BDEs in Ethers

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parantheses)

References

2-Chloroethyl ethyl ether CH2ClCH2–OC2H5

91.0G2

380.7G8.4

Derived from DfH0 in ref.

2002CRC

1-Chloroethyl methyl ether CH3CHCl–OCH3

88.5G1.5

370.3G6.3

Derived from DfH0 in ref.

1996NIST

1-Chloroethyl ethyl ether CH3CHCl–OCH3

90.1G2.0

377.0G8.4

Derived from DfH0 in ref.

1996NIST

Methyl 2-methyl-vinyl ether CH3–OC(CH3)aCH2

66.3

277.4

VLPP

1978ZAB/BEN

Methyl propyl ether CH3–OnC3H7

84.8G1.5

354.8G6.3

Derived from DfH0 in ref.

1994PED

Methyl propyl ether CH3O–nC3H7

85.7G1.5

358.6G6.3

Derived from DfH0 in ref.

1994PED

iso-Propyl methyl ether CH3–O-iso-C3H7

83.7G1.5

350.2G6.3

Derived from DfH0 in ref.

2002CRC

iso-Propyl methyl ether CH3O–iso-C3H7

86.2G1.0

360.7G4.2

Derived from DfH0 in ref.

2002CRC

Ethyl propyl ether C2H5–OC3H7

84.8G2.0

354.8G8.4

Derived from DfH0 in ref.

1986PED/NAY

Ethyl propyl ether C2H5O–C3H7

85.3G1.2

356.9G8.4

Derived from DfH0 in ref.

1986PED/NAY

Propyl vinyl ether C2H3–OC3H7

103.0G2.2

431.0G9.2

Derived from DfH0 in ref.

1986PED/NAY

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BDEs of O–X Bonds

327

Propyl vinyl ether C3H7–OC2H3

65.5G2.5

274.1G10.5

Derived from DfH0 in ref.

1994PED

Butyl methyl ether C4H9–OCH3

82.7G1.5

346.0G6.3

Derived from DfH0 in ref.

2002CRC

Butyl methyl ether C4H9O–CH3

84.4G1.5

353.1G6.3

Derived from DfH0 in ref.

2002CRC

tert-Butyl methyl ether tert-C4H9–OCH3

84.4G1.5

353.1G6.3

Derived from DfH0 in ref.

1986PED/NAY

tert-Butyl methyl ether tert-C4H9O–CH3

82.2G1.5

343.9G6.3

Derived from DfH0 in ref.

2002CRC

Butyl vinyl ether nC4H9O–C2H3

100.2G2

419.2G8.4

Derived from DfH0 in ref.

1986PED/NAY

Butyl vinyl ether nC4H9–OC2H3

65.3G2.5

273.2G10.5

Derived from DfH0 in ref.

2002CRC

tert-Butyl ethyl ether tert-C4H9–OC2H5

83.4G1.5

348.9G6.3

Derived from DfH0 in ref.

2002CRC

tert-Butyl ethyl ether tert-C4H9O–C2H5

82.9G1.5

346.9G6.3

Derived from DfH0 in ref.

2002CRC

Dipropyl ether C3H7–OC3H7

86.5G2.2

361.9G9.2

Derived from DfH0 in ref.

1986PED/NAY

(continued)

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Table 6.3.2 (continued) O–C BDEs in Ethers

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parantheses)

References

Diiso-propyl ether iso-C3H7–O-iso-C3H7

85.3G2.0

356.9G8.4

Derived from DfH0 in ref.

1986PED/NAY

2-Ethyl-2-methylpropane (C2H5)C(CH3)2–OCH3

85.3G2.0

356.9G8.4

Derived from DfH0 in ref.

1994PED

tert-Butyl isopropyl ether tert-C4H9–O-iso-C3H7

85.6G2.0

358.2G8.4

Derived from DfH0 in ref.

1994PED

tert-Butyl isopropyl ether tert-C4H9O–iso-C3H7

86.1G2.0

360.2G8.4

Derived from DfH0 in ref.

1994PED

Dibutyl ether nC4H9–O-nC4H9

83.3G2.0

348.5G8.4

Derived from DfH0 in ref.

1986PED/NAY

Disec-butyl ether sec-C4H9–O-sec-C4H9

85.9G2.0

359.4G8.4

Derived from DfH0 in ref.

1986PED/NAY

Ditert-butyl ether tert-C4H9–O-tert-C4H9

77.6G2.0

324.7G8.4

Derived from DfH0 in ref.

1986PED/NAY

Butyl tert-butyl ether nC4H9–O-tert-C4H9

84.1G2.0

351.9G8.4

Derived from DfH0 in ref.

1994PED

Butyl tert-butyl ether nC4H9O–tert-C4H9

83.2G2.0

348.1G8.4

Derived from DfH0 in ref.

1994PED

sec-Butyl tert-butyl ether tert-C4H9–O-sec-C4H9

85.8G2.0

359.0G8.4

Derived from DfH0 in ref.

1994PED

sec-Butyl tert-butyl ether tert-C4H9O–sec-C4H9

86.5G2.0

361.9G8.4

Derived from DfH0 in ref.

1994PED

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BDEs of O–X Bonds

329

iso-Butyl tert-butyl ether iso-C4H9–O-tert-C4H9

84.4G2.0

353.1G8.4

Derived from DfH0 in ref.

1994PED

Pentyl tert-butyl ether nC5H11-O–tert-C4H9

83.5G2.0

349.4G8.4

Derived from DfH0 in ref.

1994PED

Methoxybenzene or anisole C6H5–OCH3

100.1G1.4

418.8G5.9

Derived from DfH0 in ref.

1986PED/NAY

Methoxybenzene or anisole CH3–OC6H5

(1) 64.8 (2) 65.2

271.1 272.8

(1) 1989SUR/KAF (2) 1993ARE/LOU

(3) 65.3 (4) 62.9G1.0

273.2 263.2G4.2

(1) VLPP (2) Tubular flow reactor (3) VLPP (4) Derived from DfH0 in ref.

254.4

VLPP

1989SUR/KAF

269.4 257.7 261.1 266.5 256.5 261.1 258.6 264.0 234.7 253.1 266.9 235.6 243.1 255.2 261.9 263.6 254.8 257.7 261.1 248.1 256.1 248.1 260.2 255.2 266.5

VLPP

(1) 1989SUR/KAF(b) (2) 1989SUR/KAF (3) 2001PRA/HEE

Methyl pentafluorophenyl ether 60.8 CH3–OC6F5

(3) 2001PRA/HEE (4) 1986PED/NAY

Anisoles, substituted Y YZm-F

O

o-F p-F m-Cl o-Cl p-Cl o-Br m-NH2 o-NH2 p-NH2 m-OH o-OH p-OH m-Me o-Me p-Me m-MeO o-MeO p-MeO o-CH2OH m-COCH3

CH3

(1) (1) (1) (2) (2) (2) (2) (1) (1) (1) (2) (2) (3) (2) (3) (1) (1) (1) (2) (2) (3) (2) (3) (1) (1)

64.4 61.6 62.4 63.7 61.3 62.4 61.8 63.1 56.1 60.5 63.8 56.3 58.1 61.0 62.6 63.0 60.9 61.6 62.4 59.3 61.2 59.3 62.2 61.0 63.7

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.3.2 (continued) O–C BDEs in Ethers

The broken bonds (boldfaceZdissociated group) o-COCH3 p-COCH3 o-CHaCH2 m-CN o-CN p-CN m-NO2 o-NO2 p-NO2 p-CF3 2-CHO-4-OH

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (1) (1) (1) (1) (1) (4) (1) (1) (1) (3) (3)

62.0 64.1 61.0 64.6 63.4 63.8 73.6 63.0 62.1 64.6 67.5 62.3

kJ/mol 259.4 268.2 255.2 270.3 265.3 266.9 307.9 263.6 259.8 270.3 282.4 260.7

Methods (reference in parantheses)

References

(4) Electrochem.

(4) 2002AND/FAR

Ethyl phenyl ether C2H5–OC6H5

(1) 64.1 (2) 64.3G1.2

268.2 269.0G4.8

(1) VLPP (2) Derived from DfH0 in ref.

(1) 1977COL/ZAB (2) 1986PED/NAY

Ethyl phenyl ether C2H5O–C6H5

99.6G1.3

416.7G5.4

Derived from DfH0 in ref.

1996NIST

Phenyl vinyl ether C2H3,–OC6H5

(1) 70.0 (2) 77.8G1.2

292.9 325.5G4.8

(1) 1993HEN (2) 1986PED/NAY

(3) 76.0

318.0

(1) Pyrolysis (2) Derived from DfH0 in ref. (3) Pyrolysis

(1) 76.6G5

320.5G20.9

(1) 1986PED/NAY

(2) 75.9

317.6

(1) Derived from DfH0 in ref. (2) Pyrolysis

(1-Methoxyethyl)benzene C6H5CH(CH3)–OCH3

74.9G2.3

313.4G9.6

Derived from DfH0 in ref.

2001VER/HEI

(1-Ethoxyethyl)benzene C6H5CH(CH3)–OC2H5

74.6 G2.3

312.1G9.6

Derived from DfH0 in ref.

2001VER/HEI

(1-Propoxyethyl)benzene C6H5CH(CH3)–OC3H7

75.5G2.3

315.9G9.6

Derived from DfH0 in ref.

2001VER/HEI

Phenyl vinyl ether C2H3O–C6H5

7366—CHAPTER 6—5/2/2007—11:11—JEBA—15362—XML MODEL B – pp. 255–368

(3) 1997SCH/DOR

(2) 1997SCH/DOR

BDEs of O–X Bonds

331

(1-iso-Propoxyethyl)benzene C6H5CH(CH3)–OCH(CH3)2

72.9G2.3

305.0G9.6

Derived from DfH0 in ref.

2002VER/HEI

(1-Butoxyethyl)benzene C6H5CH(CH3)–C4H9

73.0G2.3

305.4G9.6

Derived from DfH0 in ref.

2001VER/HEI

(1-sec-Butoxyethyl)benzene C6H5CH(CH3)–O-sec-C4H9

73.5G2.3

307.5G9.6

Derived from DfH0 in ref.

2001VER/HEI

Diphenyl ether C6H5–OC6H5

(1) 75.0 (2) 78.1G1

313.8 326.8G4.2

(1) 1993ARE (2) 1986PED/NAY

(3) 78.7

329.4

(1) Pyrolysis (2) Derived from DfH0 in ref. (3) Pyrolysis

Allyl phenyl ether CH2aCHCH2–OC6H5

49.8G2

208.4G8.4

VLPP

1977COL/ZAB

Phenyl benzyl ether C6H5CH2–OC6H5

52.1

218.0

Pyrolysis

1993ARE

(1) 57.5 (2) 61.6

240.6 257.7

(1) VLPP (2) Electrochem.

(1) 1989SUR/KAF (2) 2002AND/FAR

61.0

255.2

VLPP

1989SUR/KAF

w68

w285

Photolysis

1997ADM/SCH

(3) 1997SCH/DOR

Naphonyl ethers, substituted 4

O

1 3 2

R

RZCH3

3,4-Benzoanisole 4

3 2

1

O

CH3

1-[(4-Benzolphenoxy)methyl]naphthalene 4-PhC(O)C6H4O–CH2K1C8H7

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.3.2 (continued) O–C BDEs in Ethers

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parantheses)

References

Piperidinol, substituted R

O CH3

CH3

N

CH3

CH3 RZCH3 c-C6H11 C6H7(1,4-cyclohexadienyl) C4H7O(a-tetrahydrofuryl) (C2H5)2NCHCH3 C6H5CH2 C6H5CHCH3 C6H5C(CH3)2

(1) (2) (2) (2) (2) (3) (3) (3)

47G1 40G1 18G1 48G1 38G1 32 30 26

196.6 167.4 75.3 200.8 159.0 133.9 126 108.8

(1) VLPP (2) PAC

1999CIR/KOR

30.6 28.4 24.6 31.4

128.0 118.8 102.9 131.4

Thermolysis

1998SKE/BEL

(1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (1) (2)

106.7G6.3 112 107.9G1.7 108 120.1G2.5 120 118.0G2.5 92 129.3G3.3 129 123.0G1.7 123

AOP

(1) 1993ARN/FLO(b) (2) 1996HAN/HUA

(3) Re-analyzed

(Phenylmethoxy) piperidine, substituted X O R1

N

R2

R1 R2 X H H H Me H H Me Me H H H OH Tropylium phenoxides, substituted Y

O

YZH F Cl Br Me NO2 CN

25.5G0.5 26.8 25.8G0.4 25.8 28.7G0.6 28.7 28.2G0.6 22.0 30.9G0.8 30.8 29.4G0.4 29.4

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BDEs of O–X Bonds

MeO MeC(O)

333

(1) 21.4G0.5 (2) 21 (2) 29.4

89.5G2.1 88 123

25.3 27.2 22.0 20.8 28.0

106 114 92 87 117

AOP

1996HAN/HUA

37.0 34.7 39.7 34.4 32.5 34.4 31.8 39.0 39.7 39.9

155 145 166 144 136 144 133 163 166 167

AOP

1996HAN/HUA

Phenylxanthylium phenoxides, substituted Y

O

Ph

O

YZH p-CN p-Me p-MeO p-MeC(O) Thiphenylmethylium phenoxides, substituted

Y

O

CPh3

YZH p-F p-Cl p-Br p-Me p-tBu p-MeO p-MeC(O) p-CN p-NO2

6.3.3

O–C bonds in acids, esters and anhydrides

Table 6.3.3 O–C BDEs in Acids, Ethers and Anhydrides

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Methyl formate CH3–OC(O)H

(1) 86.8 (2) 91.7G3

363.2 383.7G12.6

(1) ECD (2) Derived from DfHo in ref.

(1) 1989CHE/ALB (2) 1996NIST

Formic acid HC(O)–OH

109.4G0.5

457.7G2.1

Derived from DfHo in ref.

1994LIA/LIE

(continued)

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Table 6.3.3 (continued) O–C BDEs in Acids, Ethers and Anhydrides

The broken bonds (boldfaceZdissociated group) Acetic acid CH3C(O)–OH

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses) (1) Derived from DfHo in ref. (2) Derived

References (1) 1994LIA/LIE

(1) 109.8G1

459.4G4.2

(2) 109.0

456.2

Propenoic acid C2H3C(O)–OH

107.2G2.5

448.5G10.5

Derived from DfHo in ref.

1996NIST

Propanoic acid C2H5C(O)–OH

(1) 110.1G2

460.8G8.4

(1) 1986PED/NAY

(2) 106.1

444.0

(1) Derived from DfHo in ref. (2) Derived

(2) 2005TUM/DEN

Butanoic acid C3H7C(O)–OH

109.3

457.5

Derived

2005TUM/DEN

2-Methyl-propanoiacid iso-C3H7C(O)–OH

107.8

451.2

Derived

2005TUM/DEN

Pentanoic acid C4H9C(O)–OH

109.7

458.8

Derived

2005TUM/DEN

2-Methyl-butanoic acid C2H5CH(CH3)C(O)–OH

108.7

454.8

Derived

2005TUM/DEN

2,2-Dimethyl-propanoiacid tert-C4H9C(O)–OH

110.9

463.8

Derived

2005TUM/DEN

Decanoic acid nC9H19C(O)–OH

109.3

457.3

Derived

2005TUM/DEN

Benzoic acid C6H5C(O)–OH

(1) 107.0G2.5

447.7G10.5

(1) 1996NIST

(2) 101.7

425.4

(1) Derived from DfHo in ref. (2) Derived

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(2) 2005TUM/DEN

(2) 2005TUM/DEN

BDEs of O–X Bonds

335

2-Phenylacetic acid C6H5CH2C(O)–OH

106.7

446.6

Derived

2005TUM/DEN

Glycolic acid HO–CH2C(O)OH

88.0G2.5

368.2G10.5

Derived from DfHo in ref.

2001DOR/NOV

Methyl acetate CH3C(O)O–CH3

90.9G3

380.3G12.6

Derived from DfHo in ref.

2002CRC

Methyl formate HC(O)–OCH3

101.8G1

425.9G4.2

Derived from DfHo in ref.

1994PED

Methyl acetate CH3C(O)–OCH3

101.4G1.5

424.3G6.3

Derived from DfHo in ref.

2002CRC

Ethyl chloroformate ClC(O)–OC2H5

102.2G2

427.6G8.4

Derived from DfHo in ref.

20023CRC

Methyl acrylate CH2aCHC(O)–OCH3

99.3G2

415.5G8.4

Derived from DfHo in ref.

1988LIA/BAR

Ethyl acetate C2H5–OC(O)CH3

91.7G3

383.7G12.6

Derived from DfHo in ref.

1986PED/NAY

Ethyl acetate C2H5O–C(O)CH3

100.5G3

420.5G12.6

Derived from DfHo in ref.

1986PED/NAY

iso-Propyl acetate iso-C3H7–OC(O)CH3

93.1G3

389.5G12.6

Derived from DfHo in ref.

1994PED

Butyl acetate nC4H9–OC(O)CH3

91.6G3

383.3G12.6

Derived from DfHo in ref.

2002CRC

tert-Butyl acetate tert-C4H9–OC(O)CH3

91.9G3.5

384.5G14.6

Derived from DfHo in ref.

1996NIST

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.3.3 (continued) O–C BDEs in Acids, Ethers and Anhydrides

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Phenyl acetate C6H5–OC(O)CH3

102.9G3.5

430.5G14.6

Derived from DfHo in ref.

1996NIST

Methyl benzoate CH3–OC(O)C6H5

(1) 87.5G4 (2) 89.1G4

366.1G16.7 372.8G16.7

Derived from DfHo in ref.

(1) 1996NIST (2) 2002ROU/TEM

Phenyl benzoate C6H5–OC(O)C6H5

103.2G4

431.8G16.7

Derived from DfHo in ref.

1996NIST

Vinyl acetate CH3C(O)–OC2H3

75.8G1.5

317.1G6.3

Derived from DfHo in ref.

2002CRC

Vinyl acetate CH3C(O)–OC2H3

80.3G3

336.0G12.6

Derived from DfHo in ref.

1994PED

Formic acid phenyl ester HC(O)–OC6H5

73.1G2

305.9G8

Derived from DfHo in ref.

1994PED

Acetic acid phenyl ester CH3C(O)–OC6H5

76.0G2

318.0G8.4

Derived from DfHo in ref.

1986PED/NAY

Methyl benzoate C6H5C(O)–OCH3

(1) 100.7G3 (2) 98.8G3

421.3G12.6 413.4G12.6

Derived from DfHo in ref.

(1) 1996NIST (2) 2002ROU/TEM

Phenyl benzoate C6H5C(O)–OC6H5

75.7G2

316.7G8.4

Derived from DfHo in ref.

1996NIST

Dimethoxymethane CH3OCH2–OCH3

87.8G2

367.5G8.4

Derived from DfHo in ref.

2002CRC

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BDEs of O–X Bonds

337

Acetic anhydride CH3C(O)–OC(O)CH3

(1) 83.5 (2) 91.4G3

349.4 382.4G12.6

(1) ECD (2) Derived from DfHo in ref.

(1) 1989CHE/ALB (2) 1986PED/NAY

Benzoic anhydride C6H5C(O)–OC(O)C6H5

92.0G4

384.9G16.7

Derived from DfHo in ref.

1986PED/NAY

6.3.4

O–C bonds in peroxides and peroxys

Table 6.3.4 O–C BDEs in Peroxides and Peroxys

The broken bonds (boldfaceZ dissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses) 0

References

Methyl hydroperoxide CH3–OOH

71.8G3

300.4G12.6

Derived from DfH in ref.

2001DOR/NOV

Ethyl hydroperoxide C2H5–OOH

79.4G5

332.2G20.9

Derived from DfH0 in ref.

1986PED/NAY

Propyl hydroperoxide nC3H7–OOH

87.1

364.4

Derived from DfH0 in ref.

1996NIST

iso-Propyl hydroperoxide iso-C3H7–OOH

71.3

298.3

Derived from DfH0 in ref.

1996NIST

tert-Butyl hydroperoxide tert-C4H9–OOH

73.9G1

309.2G4.2

Derived from DfH0 in ref.

1986PED/NAY

Hexyl-1 hydroperoxide nC6H13–OOH

70.1

293.3

Derived from DfH0 in ref.

1969BDE/CRU

Hexyl-2 hydroperoxide (n-Bu)(Me)C–OOH

71.6

299.6

Derived from DfH0 in ref.

1969BDE/CRU

(continued)

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Table 6.3.4 (continued) O–C BDEs in Peroxides and Peroxys

The broken bonds (boldfaceZ dissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Hexyl-3 hydroperoxide (iso-Pr)(Et)C–OOH

69.4

290.4

Derived from DfH0 in ref.

1969BDE/CRU

Heptyl-2 hydroperoxide (nC5H11)(Me)C–OOH

72.3

302.5

Derived from DfH0 in ref.

1969BDE/CRU

cyclo-Hexyl hydroperoxide cyclo-C6H11–OOH

73.8

308.8

Derived from DfH0 in ref.

1969BDE/CRU

Dimethyl peroxide CH3–OOCH3

(1) 67.3G1.5 (2) 69.9G2

281.6G6.3 292.5G8.4

Derived from DfH0 in ref.

(1) 1986PED/NAY (2) 2001DOR/NOV

Bis(trifluoromethyl) peroxide CF3–OOCF3

86.4G2

361.5G8.4

Pyrolysis

1983BAT/WAL

Diethyl peroxide C2H5–OOC2H5

67.7G2.5

283.2G10.5

Derived from DfH0 in ref.

1969BDE/CRU

tert-Butylperoxide tert-C4H9–OO-tert-C4H9

70.7G2

295.8G8.4

Derived from DfH0 in ref.

1986PED/NAY

Methyl peroxy CH3–OO

(1) O30.3 (2) 32.2G1.5 (3) 32.4G0.7 (4) 32.7G0.9

O126.8 134.7G6.5 135.6G2.9 137.0G3.8

(1) VLPR (2) Equilibrium (3) Derived (4) Re-analyzed

(1) 1984KON/BEN (2) 1982KHA/NIA (3) 1992LIG/COX (4) SLA(b/SLA(b)

Trifluoromethyl peroxy CF3–OO

40.4

169.0

Derived from DfH0 in ref.

2004JAN/ROS

Chlorodifluoromethyl peroxy CClF2–OO

30.5

127.6

Derived from DfH0 in ref.

1992LIG/COX

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BDEs of O–X Bonds

339

Dichlorofluoromethyl peroxy CCl2F–OO

29.8

124.7

Derived from DfH0 in ref.

1992LIG/COX

Chloromethyl peroxy CH2Cl–OO

(1) 28.9 (2) 29.3G2.5

120.9 122.4G10.5

(1) Derived (2) Re-analyzed

(1) 1992LIG/COX (2) 1998KNY/SLA(b)

Dichloromethyl peroxy CHCl2–OO

(1) 25.3 (2) 25.9G2.0

105.9 108.2G8.2

(1) Derived (2) Re-analyzed

(1) 1992LIG/COX (2) 1998KNY/SLA(b)

Trichloromethyl peroxy CCl3–OO

(1) 19.7G0.9 (2) 22G1.5

82.4G3.8 92.0G6.4

(1) Derived (2) Re-analyzed

(1) 1992LIG/COX (2) 1998KNY/SLA(b)

Ethyl peroxy C2H5–OO

(1) 34.1G0.5 (2) 35.2G1.5 (3) 31.3G1.1 (4) 35.5G2.0

142.7G2.1 147.2G6.3 131.0G4.6 148.4G8.4

(1) PIMS (2) Derived (3) Review (4) Re-analyzed

(1) 1990WAG/SLA (2) 1992LIG/COX (3) 1997BEN/COH (4) 1998KNY/SLA(b)

Vinyl peroxy C2H3–OO

47.3G1.0

197.9G4.0

Derived from DfHo in ref.

2002SEB/BOC

2-Chloroethyl peroxy CH3CHCl–OO

31.4G0.4

131.2G1.8

Re-analyzed

1998KNY/SLA(b)

2,2-Dichloroethyl peroxy CH3CCl2–OO

26.8G0.5

112.2G2.2

Re-analyzed

1998KNY/SLA(b)

iso-Propyl peroxy iso-Pr–OO

(1) 39.7 (2) 37.7G1.8 (3) 32.2G1.3 (4) 37.1G2.3

166.1 157.9G7.5 134.7G5.4 155.4G9.6

(1) PIMS (2) Derived (3) Review (4) Re-analyzed

(1) 1985SLA/RAT (2) 1992LIG/COX (3) 1997BEN/COH (4) 1998KNY/SLA(b)

Allyl peroxy CH2ZCHCH2–OO

(1) 18.2 (2) 18.4

76.1 77.0

(1) Photolysis (2) PIMS detect.

(1) 1982MOR/PIL (2) 1998KNY/SLA

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.3.4 (continued) O–C BDEs in Peroxides and Peroxys BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated group) 2-Chloroallyl peroxy CH2CClCH2–OO

kcal/mol 18.3G0.7

kJ/mol

Methods (reference in parentheses)

References

76.5G2.8

PIMS

2005SHE/KNY

2-Chloro-2-methylethyl-peroxy 32.5G0.9 (CH3)2CCl–OO

136.0G3.8

Re-analyzed

1998KNY/SLA(b)

tert-Butyl peroxy tert-Bu–OO

(1) 30.2G1.1 (2) 36.7G1.9 (3) 36.7G1.9 (4) 36.5G1.8

126.4G4.6 153.6G7.9 153.6G7.9 152.8G7.4

(1) VLPR (2) PIMS (3) Derived (4) Re-analyzed

(1) 1983HEN/BEN (2) 1986SLA/RAT (3) 1992LIG/COX (4) 1998KNY/SLA(b)

Butenyl-2-peroxy CH3CHCHCH2–OO

15.2G2.0

63.6G8.4

Derived from DfH0 in ref.

1998KNY/SLA

Pentadienyl peroxy (CH2CH)2CH–OO

13.4G1.2

56G5

Pulsed LP

2001ZIL/INO

neo-Pentyl peroxy neo-C5H11–OO

36.3

151.9

Derived from DfH0 in ref.

2004SUN/BOZ

cyclo-Hetyl peroxy cyclo-C6H11–OO

24

100.4

PAC

2000KRA/CIR

cyclo-Hexenyl peroxy cyclo-C6H9–OO

19.2G1.0

80.4G4.2

Pulsed LP

1998ZIL/INO

cyclo-Hexadienyl peroxy cyclo-C6H7–OO

12

50.2

PAC

2000KRA/CIR

Benzyl peroxy C6H5CH2-OO

(1) 22G1.5 (2) 21G1

92.0G6 87.9G4.2

(1) Photolysis (2) LIF

(1) 1993FEN/NOZ (2) 1993ELM/MIN

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BDEs of O–X Bonds

341

a-OH-methyl peroxy HOCH2–OO

(1) 16.3G0.3 (2) 34.6

68.2G1.3 144.8

(1) Review (2) Derived from DfH0 in ref.

(1) 1997BEN/COH (2) 1992LIG/COX

Vinoxy peroxy HC(O)CH2–OO

24.1G1

101G4

LP

2006DEL/FIT

1-Methylvinoxy peroxy CH3C(O)CH2-OO

25.1G0.5

105G2

LP

2006HAS/DEL

Adduct of hydroxycyclohexadienyl C6H6(OH)–OO

10.4G0.5

43.6G2

UV absorption

2004GRE/KRA

a-NH2-methyl peroxy NH2CH2–OO

36.5G1.8

152.8G7.4

Re-analyzed

1998KNY/SLA(b)

Pyrrolidin-2-yl-peroxy cyclo-C4H8N-OO

10

41.8

PAC

2000KRA/CIR

(Ethylmethylamino)methylperoxy (C2H5)N(CH3)CH2–OO

25

104.6

PAC

2000KRA/CIR

Acetyl peroxy CH3C(O)–OO

34.5G2

144.4G8.4

Derived from DfH0 in ref.

2003NASA/JPL

Zeroane HC(O)–OOH

69.3

290.0

Derived from DfH0 in ref.

2003FEL/DIX

Acetyl peroxide CH3C(O)–OOC(O)CH3

75.3

315.1

Derived from DfH0 in ref.

1969BDE/CRU

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6.3.5

Comprehensive Handbook of Chemical Bond Energies

O–C bonds in other species

Table 6.3.5 O–C BDEs in Other Species

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Carbon monoxide C–O

257.26G0.16

1076.38G0.67

Derived from DfH0 in ref.

1998CHA

Carbon dioxide OZCO

127.2G0.1

532.2G0.4

Spectroscopy

1970DAR

Carbon oxysulfide OZCS

(1) 159.9G0.9 (2) 159.7G0.3

668.9G3.8 668.0G1.4

(1) GIB MS (2) Derived from DfH0 in ref.

1990PRI/ARM 1996NIST

Formaldehyde, halogened CF2ZO CCl2ZO CBr2ZO

168.8 166.2 164.1

706.1 695.2 686.4

Derived from DfH0 in ref.

1996NIST

Formaldehyde

180.6

755.6

Derived from DfH0 in ref.

1996NIST

Methanisocynate OZCNCH3

133G4

556.5G16.7

Review

1978BEN

Trifluoromethyl hypochlorite ClO–CF3

%88.4G0.3

%369.9G1.3

PIMS

1997ASH/APP

Methyl nitrite CH3–ONO

58.6

245.2

Derived from DfH0 in ref.

1996NIST

Ethyl nitrite C2H5–ONO

62.2

260.2

Derived from DfH0 in ref.

1996NIST

OZCH2

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BDEs of O–X Bonds

343

Propyl nitrine nC3H7–ONO

59.6G1.5

249.4G6.3

Derived from DfH0 in ref.

1996NIST

iso-Propyl nitrine iso-C3H7–ONO

60.8G1.5

254.4G6.3

Derived from DfH0 in ref.

1996NIST

Butyl nitrine nC4H9–ONO

61.3G1.5

256.5G6.3

Derived from DfH0 in ref.

1996NIST

iso-Butyl nitrine iso-C4H9–ONO

60.7G1.5

254.0G6.3

Derived from DfH0 in ref.

1996NIST

sec-Butyl nitrine sec-C4H9–ONO

60.6G1.5

253.6G6.3

Derived from DfH0 in ref.

1996NIST

tert-Butyl nitrine tert-C4H9–ONO

60.4G1.5

252.7G6.3

Derived from DfH0 in ref.

1996NIST

2-Methylbytanyl nitrine (C2H5)(CH3)2C–ONO

60.7G2

254.0G8.4

Derived from DfH0 in ref.

1996NIST

Methyl nitrate CH3–ONO2

(1) 81.9G0.5

342.7G2.1

(1) 1996NIST

(2) 81.0

338.9

(1) Derived from DfH0 in ref. (2) Derived

(1) 83.0G1.0

347.3G4.1

(1) 1996NIST

(2) 79.5

332.6

(1) Derived from DfH0 in ref. (2) Derived

Propyl nitrate nC3H7–ONO2

79.6

333.0

Derived

2001/MIR/KOS

iso-Propyl nitrate iso-C3H7–ONO2

80.2

335.6

Derived

2001MIR/KOS

Ethyl nitrate C2H5–ONO2

(2) 2001MIR/KOS

(2) 2001MIR/KOS

(continued)

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344

Comprehensive Handbook of Chemical Bond Energies

Table 6.3.5 (continued) O–C BDEs in Other Species

The broken bonds (boldfaceZdissociated atom or group) Nitrates R–ONO2 RZCH2CH2ONO2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

73.5

307.4

CH2CH(ONO2)CH2ONO2

77.2

323.0

CH2C(CH2ONO2)3

74.2

310.5

CH(CH2ONO2)2

69.6

291.2

(1) 79.7 (2) 82.1

1-Methoxy-1,1-dimethyl-1silaethane Me–OsiMe3

1-Ethoxy-1,1-dimethyl-1silaethane Et–OSiMe3

Methods (reference in parentheses)

References

Derived

2001MIR/KOS

333.3 343.6

(1) Derived (2) Derived from DfH0 in ref.

2002MIR/LEB

96.3

403

Derived

1998BEC/WAL

98.5

412

Derived

1998BEC/WAL

61.2

256

Derived

1997DOR/PUG

60.5

253

Derived

1997DOR/PUG

60.9

255

Derived

1997DOR/PUG

1-Adamantyl nitrate ONO2 1 2

2H-3,4-Dihydropyran O

2,3-Dihydro-1,4-dioxin O O

Chromane O

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BDEs of O–X Bonds

345

2,3-Dihydro-1,4-benzodioxin O 60.2

252

Tubular flow reactor

1994SCH/ARE

(1) 58.8 (2) 62.2

246.0 260.2

(1) Derived (2) Derived from DfH0 in ref.

2002MIR/LEB

Methoxyacetonitrile CH3O–CH2CN

94.0

393.3

Derived from DfH0 in ref.

1996NIST

Ethoxyacetonitrile C2H5O–CH2CN

94.0

393.3

Derived from DfH0 in ref.

1996NIST

Methoxy-1-thiol HSO–CH3

50G5

209G21

Est. by exp.

2000AMA/WIE

Methoxymethylthio CH3SO–CH3

48G4

201G17

Est. by exp.

2000AMA/WIE

w28

w117

NMR

2000AMA/WIE

!33G10

!138G42

Est. by exp.

1997CRE/MAY

O

1-Nitroadamantane ONO2 1 2

Cinnamyl-4-nitrobenzene sulfonate p-NO2–C6H4SO–R RZCH2CHCHC6H5

Tungsten alkoxide WO-alkyl

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6.3.6

Comprehensive Handbook of Chemical Bond Energies

O–C bonds in radicals

Table 6.3.6 O–C BDEs in Radicals

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

HO–C%H2

106.3G1

444.8G4.2

Derived

This volume

HO–CHClC%H2 HO–CCl2C%H2

31.4G3 33.2G3

131.4G12.6 138.9G12.6

Derived from DfH0 in ref.

1996NIST

HO–CH2C%H(CH3)

32.6G3

136.4G12.6

HO–CH2C%H2

30.1G2.5

125.9G10.5

28.8G3

120.5G12.6

HO–C(CH3)2C H2

39.8G3

166.5G12.6

CH3–O%

90.1G0.8

377.0G3.3

Derived from DfH0 in ref.

2002ERV/DET

CH2ZCHCH2–O%

79.7G1

333.5G4.2

Derived from DfH0 in ref.

2000LEE/CHE

C6H5CH2–O%

82.4G3

344.8G12.6

Derived

This volume

HC(O)–O%

99.8G3

417.6G12.6

CH3–OC%H2 CH3–OC%HCH3

9.1G2 8.1G2

38.1G8.4 33.9G8.4

Derived from DfH0 in ref.

1996NIST

CH3CH2–OC%H2

13.2G3

55.2G12.6

CH3CH2–OC HCH3

7G3

29.3G12.6

C6H5C(O)–OC%H2

18.5G3

77.4G12.6

trans-HO–C%(O)

29.0G1

121.3G4.2

1996NIST

cis-HO–C (O)

35.0

146.4

Derived from DfH0 in ref.

CH3–OC%(O)

K16.6G2

K69.5G8.2

16.7G2

69.9G8.2

Derived from DfH0 in ref.

1996NIST

CH3O–C%(O)

HO–CH(CH3)C%H2 %

%

%

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BDEs of O–X Bonds

347

HO–C(O)C%H2

47.5G4

198.7G16.7

CH3O–C(O)C%H2

40.2G3

168.2G12.6

CH3CH2O–C(O)C%H2

44.9G3

187.9G12.6

C6H5O–C(O)C H2

K2.6G2

10.9G8.4

CF3O–CO2

K17G5

K71G21

Derived from DfH0 in ref.

2005PAC/ARG

HOO–CH2C%H2 –CH2C%HCH3

4.7G1.5 5.6G2

19.7G6.3 23.4G8.4

Derived from DfH0 in ref.

1996NIST

–CH(CH3)C%H2

7.5G2.5

31.4G10.5

–CH2C%(CH3)2

6.2G2.5

25.9G10.5

–C(CH3)2C H2

5.4G2.5

22.6G10.5

–C(O)C%H2

15.4G2.5

64.4G10.5

%

%

6.4

O–N bonds

Table 6.4 O–N BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Nitric oxide O–N

(1) 150.71G0.03 (2) 150.96G0.04

630.57G0.13 631.62G0.18

(1) Spectrometry (2) Review

(1) 1979HUB/HER (2) 2005ACR/PIL

Dinitrogen oxide O–N2

(1) 39.0G0.5 (2) 40.0G0.1

163.2G2.1 167.4G0.4

(1) Photo impact (2) Derived from DfH0 in ref.

(1) 1967DIB (2) 2002CRC

Nitrogen dioxide O–NO

(1) 72.9 (2) 73.22G0.20

305.0 306.36G0.82

(1) 1965BEN (2) 1996NIST

(3) 73.19G0.10 (4) 73.21G0.03

306.24G0.41 306.31G0.13

(1) Review (2) Derived from DfH0 in ref. (3) Review (4) Derived

(3) 2005ACR/PIL (4) 2006RUS/PIN

16

71.846G0.001, 0K

300.604G0.004

LIF

2004MIC/JOS

18

71.932G0.001

300.965G0.004

16

71.883G0.001 71.970G0.001

300.759G0.004 301.121G0.001

O–14N16O O–14N18O

O–15N16O 18 O–15N18O

(continued)

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Table 6.4 (continued) O–N BDEs

The broken bonds (boldfaceZdissociated atom or group) O–14N18O

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

16

71.853G0.001

300.632G0.004

16

71.890G0.001

300.787G0.004

Nitrate O–NO2

(1) 48.7G0.3 (2) 49.3G0.3

203.8G1.4 206.3G1.4

(1) PD (2) Derived from DfH0 in ref.

(1) 1993DAV/KIM (2)2001IUPAC

Dinitrogen tetroxide O–N(O)NO2

77.2

322.9

Derived from DfH0 in ref.

1998CHA

Nitric oxide dimer NO–NO

9.7G0.5

40.6G2.1

Review

1976BEN

Dinitrogen pentoxide O2N–ONO2

22.8G0.4

95.4G1.5

Derived from DfH0 in ref.

2001IUPAC

Nitrosyl hydride HO–N

98.1

410.4

Derived from DfH0 in ref.

1996NIST

Nitrous acid cis-HO–NO

49.5

207.0

Derived from DfH0 in ref.

2001IUPAC

trans-Nitrous acid trans-HO–NO

47.95G0.05, 0 K 200.64G0.19

DROPS

2000REI/ABE

Fluoronitrooxy FO–NO

31.7G4

132.5G17

Derived from DfH0 in ref.

2003NASA/JPL

cis-Chloronitrooxy cis-ClO–NO

30.5G2

127.6G8.4

Derived from DfH0 in ref.

2003NASA/JPL

O–15N18O

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BDEs of O–X Bonds

349

trans-Chloronitrooxy trans-ClO–NO

27.9G2

116.6G8.4

Derived from DfH0 in ref.

2003NASA/JPL

cis-Bromonitrooxy cis-BrO–NO

33.0G2

138.1G8.4

Derived from DfH0 in ref.

2003NASA/JPL

trans-Bromonitrooxy trans-BrO–NO

29.1G2

121.6G8.4

Derived from DfH0 in ref.

2003NASA/JPL

trans-Perp-HOONO HOO–NO

27.3G1

114.2G4

Derived

2002HIP/NAS

Methyl nitrite CH3O–NO

(1) 41.8G1 (2) 42.2G0.8

174.9G4.2 176.6G3.3

(1) Pyrolysis (2) Derived from DfH0 in ref.

(1) 1977BAT/MIL (2) 1996NIST

Ethyl nitrite C2H5O–NO

(1) 42.0G1.3 (2) 44.3G1.0

175.7G5.4 185.4G4.2

(1) Pyrolysis (2) Derived from DfH0 in ref.

(1) 1977BAT/MIL (2) 1996NIST

Propyl nitrite nC3H7O–NO

(1) 40.1G1.8 (2) 42.8G1.5

167.8G7.5 179.1G6.3

(1) Pyrolysis (2) Derived from DfH0 in ref.

(1) 1974BAT/CHR (2) 1996NIST

iso-Propyl nitrite iso-C3H7O–NO

(1) 41.0G1.3 (2) 41.9G1

171.5G7.5 175.3G4.2

(1) Pyrolysis (2) Derived from DfH0 in ref.

(1) 1974BAT/CHR (2) 1996NIST

Butyl nitrite nC4H9O–NO

42.5G1.5

177.8G6.5

Pyrolysis

1974BAT/CHR

iso-Butyl nitrite iso-C4H9O–NO

42.0G1.5

175.7G6.5

Pyrolysis

1974BAT/CHR

sec-Butyl nitrite sec-C4H9O–NO

41.5G0.8

173.6G3.3

Pyrolysis

1974BAT/CHR

(continued)

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Table 6.4 (continued) O–N BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

tert-Butyl nitrite tert-C4H9O–NO

(1) 40.9G0.8 (2) 42.1G1.4

171.1G3.3 176.1G5.9

(1) Pyrolysis (2) Derived from DfH0 in ref.

(1) 1974BAT/CHR (2) 1996NIST

tert-Amyl nitrite tert-AmO–NO

40.9G1

171.1G0.4

Kinetics

1979ISL

Alkyl nitrite RO–NO

40.8G1

170.7G4.2

Review

1981BAT/ROB

Phenyl nitrite C6H5O–NO

20.8

87.0

Kinetics

1998BER/CAR

Nitric acid HO–NO2

49.1

205.4

Derived from DfH0 in ref.

2001IUPAC

Fluoronitrooxy FO–NO2

31.5G3

131.8G12.6

Derived from DfH0 in ref.

2003NASA/JPL

Chloronitrooxy ClO–NO2

26.7G0.5

111.8G2.1

Derived from DfH0 in ref.

1990AND/FAH

Bromonitrooxy BrO–NO2

28.2G1.5

118.0G6.3

Kinetics

1996ORL/TYN

Iodomonitrooxy IO–NO2

(1) O25.4 (2) 22.7–32.3 (3 )w24

O106 95–135 w100

Review

(1) 1996ORL/TYN (2) 2006GOL (3) 2006DIL/BLI

Alkyl nitrate RO–NO2

40.7G0.5

170.3G2.1

Review

1981BAT/ROB

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BDEs of O–X Bonds

351

Methyl nitrate CH3O–NO2

42.1G1.0

176.1G4.2

Derived from DfH0 in ref.

1986PED/NAY

Ethyl nitrate C2H5O–NO2

41.7G1.0

174.5G4.2

Derived from DfH0 in ref.

1986PED/NAY

Propyl nitrate C3H7O–NO2

42.3G1

177.0G4.2

Derived from DfH0 in ref.

1986PED/NAY

iso-Propyl nitrate iso-C3H7O–NO2

42.0G1

175.7G4.2

Derived from DfH0 in ref.

1986PED/NAY

Nitric peracid HOO–NO2

(1) 23G2 96.2G8.4 (2) 22.8G0.8, 0 K 95.3G3.4 (3) 23.7G1.1 99.2G4.6

(1) Pyrolysis (2) Derived (3) Derived from DfH0 in ref.

(1) 1978BAL/GOL (2) 1995ZAB (3) 2005GIE/JIM

Methyl nitroperoxy CH3OO–NO2

20.7G2

86.6G8.4

Derived from DfH0 in ref.

1983PAT/GOL

Trifluoromethyl nitroperoxy CF3OO–NO2

25

105

Kinetics

1990DES/TRO

Chlorodifluoromethyl nitroperoxy CF2ClOO–NO2

25.5

106.7

Derived from DfH0 in ref.

1991KOP/ZAB

Dichlorofluoromethyl nitroperoxy CFCl2OO–NO2

25.5

106.7

Derived from DfH0 in ref.

1991KOP/ZAB

Trichloromethyl nitroperoxy CCl3OO–NO2

22.9

95.8

Derived from DfH0 in ref.

1991KOP/ZAB

Ethyl nitroperoxy C2H5OO–NO2

16.5G3

69.0G12.6

Derived from DfH0 in ref.

1990DES/TRO

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.4 (continued) O–N BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Peroxyacetyl nitrate CH3C(O)OO–NO2

(1) 26G2 (2) 28.4G0.7

108.8G8.4 118.8G2.9

(1) Pyrolysis (2) Kinetics

(1) 1977HEN/KEN (2) 1991BRI/CAR

1-Methylvinyl nitroperoxy CH2aC(CH3)OO–NO2

26G2

108.8G8.4

Pyrolysis

1977HEN/KEN

(Hydroxyimino)ethane HO–NaCHCH3

49.7

207.9

Review

1970ONE/BEN

35.2

147.3

AOP

2000XIA/ZHU

CH2CH3

37.9

158.6

CH(CH3)2

36.7

153.6

AOP

2000XIA/ZHU

Nitroso formate, substituted O R

O

NO

RZCH3

Nitroso benzoate, substituted O O

NO

Y YZH

Br

33.9

141.8

34.3

143.5

Me

32.8

137.2

MeO

32.5

136.0

NO2

38.6

161.5

Hydroxylamine HO–NH2

63.0G2

263.6G8.4

Derived from DfH0 in ref.

1999AND

Methoxyamine CH3O–NH2

54.6

228.4

Derived from DfH0 in ref.

1988LIA/BAR

N,N-Difluorohydroxylamine O-fluorosulfate FSO2O–NF2

35

146

MS

1965PAU/LUS

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BDEs of O–X Bonds

353

Methylhydroxylamine HO–NHCH3

64.9

271.5

Derived from DfH0 in ref.

1988LIA/BAR

N-Methyoxymethanamine CH3O–NHCH3

57.5

240.6

Derived from DfH0 in ref.

1994NIST

Nitro compounds CH3N(O)–O

94.0G0.8

393.4G3.5

Derived

2005ACR/PIL

(CH3)3CN(O)–O

94.9G1.2

397G5

Trialkyl-N-oxides R3N–O RZCH3

Calorimetry

1995ACR/TUC

Derived

2005ACR/PIL

(1) Derived

2005ACR/PIL

61.2G1.2

256G5

C2H5

16.0G1.2

67G5

n-C4H9

K17.7G1.4

K74G6

Nitro compounds C6H5CH2N(O)–O

93.9G0.8

393G7

(1-Adamantanyl)N(O)–O

95.6G1.2

400G5

(1) 93.7G1 (1) 90.9G0.5

392G8 380.4G2.3

2,4,6-(CH3)3

(1) 91.6G0.7

383.4G2.9

2,4,6-(tBu)3

(1) 76.9G1.7

321.7G7.0

2-NO2

(1) 78.0G0.6

326.4G2.6

4-N(CH3)2

(1) 88.8G0.8

371.4G3.5

4-OH

(2) 92.1G1.0

385.3G4.2

(2) Derived from DfHo in ref.

72G6

301G25

Derived

1993CYR/LEA

73.0G1.1

305.3G4.4

Calorimetry

2005ACR/PIL

Nitrobenzyl compounds O N Y

O

YZH 2,6-(CH3)2

Nitromethyl radical C.H2N(O)–O

Alkyl nitrate RON(O)–O RZCH3

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.4 (continued) O–N BDEs

The broken bonds (boldfaceZdissociated atom or group) C2H5 n-C3H7 iso-C3H7

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

72.2G1.1 72.7G1.0 73.3G1.0

302.0G4.6 304.3G4.3 306.7G4.3

74.2G0.6

310.3G2.4

Calorimetry

2005ACR/PIL

69.9

292.3

Calorimetry

2005ACR/PIL

Calorimetry

1996ACR/BOT

1-Nitropiperidine O

N

N

O

N-Nitromorpholine O

O

N

N

O

Furazan N-oxides, substituted Y

45

N3 21 N O

O

YZ4,5-Me2

60.8G1.0

254.2G4.0

4,5-(CH2ONO2)2

57.1G0.5

238.8G2.1

4,5-(CN)2

57.4G2.4

240G10

60.7 57.1G0.9

254.0 238.9G3.8

Calorimetry

1971MAT/PEP 1975PEP/MAT

(1) 63.3G0.5

264.9G2.0

Calorimetry

(1) 1998SIL/MAT

Furoxans R

R N

O

N O

RZCH3 CH2ONO2

Pyridine N-oxides, substituted

Y

4

YZH

5

6

3 2

1N

O

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BDEs of O–X Bonds

355

2-Me

(2) 72.1G0.7

301.7G2.8

(1) 62.1G0.6

259.9G2.4

3-Me

(1) 63.2G0.6

264.6G2.6

4-Me

(1) 62.7G0.8 (3) 65.7G1.2 (4) 62.4G0.8

262.4G3.4 274.7G5 261.1G3.4

(1) 60.8G0.7

254.3G3.1

3-CN 4-CN

(1) 63.5G1.1

265.5G4.6

2-OH

(5) 66.6G0.5

278.8G2.3

3-OH

(1) 60.9G1.1

255.0G4.8

3-HOO

(6) 60.4G0.6

252.8G2.7

2-C(O)OH

(1) 65.9G1.2

275.9G5.1

3-C(O)OH

(5) 60.4G0.6

252.8G2.7

4-C(O)OH

(1) 62.0G1.2

259.5G5.0

3-NO2

(7) 64

267.8

4-NO2

(3) 65.7G1.2 (6) 61.8G1.3

274.6G5 258.5G5.3

3-Me-4-NO2

(1) 63.0G1.7

263.4G7.1

3-NH2C(O)

(8) 71.7G1.2

300.3G5.0

4-NH2C(O)

(8) 69.0G0.9

288.6G3.7

2,4,6-(NO)3

(3) 42.3G1.2

176.8G5

4-C6H5

(9) 60.6G1.2

253.7G5.1

53.1G1.1

222.2G4.6

55.6G0.9

232.8G3.8

78.6G0.4

(2) 1988LI/PIL

(3) 1995LEB/CHI (4) 2005ACR/PIL

(5) 2004SIL/MAT (6) 1995ACR/TUC

(7) 1969MIR/LEB

(8) 2001SIL/GON

(9) 2005SOU/ACR

Benzonitrile N-oxide, substituted C

Y

N

O

YZ2,4,6-Me3 2,4,6-(MeO)3

Calorimetry

1991ACR/TUC

328.7G1.7

Derived

2005ACR/PIL

(1) 60.0G0.7

250.9G3.0

Calorimetry

(1) 1990LEI/PIL

(2) 58.3G0.8

244.1G3.5

2,3-Diazabicyclo[2.2.1]-hept2-ene N-oxide N N

O

Benzofurazan N-oxides, substituted O 6 5

Y YZH

7

N

4

N

5-Cl

1 2 3

(2) 1996ACR/BOT

(continued)

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356

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Table 6.4 (continued) O–N BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

5-Me

(2) 59.7G0.8

249.8G3.2

5-MeO 4-NO2 5-NO2

(2) 59.3G0.9 (2) 61.2G1.6 (3) 60.7G1.4

248.0G3.7 255.9G6.7 254G6

79.2G0.9 76.8G1.0

331.5G3.8 321.2G4.2

Calorimetry

1986KIR/ACR

(1) Calorimetry (2) Calorimetry, revised (3) Calorimetry

(1) 1986KIR/PIL (2) 1993ACR/TUC(b)

(4) Calorimetry

(4) 1989ACR/KIR

Calorimetry

(1) 1989ACR/KIR

(3) 2005ACR/PIL

Azoxy compounds O R

N

N

R

RZiPr tBt Azoxybenzenes, substituted O N

Y

N

Y'

E-Structure Y, Y 0 ZH

(1) 76.8G0.7 (2) 73.9G0.8

321.5G2.9 309.4G3.5

4-CH3O 4-C2H5O Z-Structure Y, Y 0 ZH

(3) 75.6G1.8 (3) 76.4G1.7 (4) 62.8G0.8

316.4G7.6 319.8G7.1 262.8G3.3

(3) 2005ACR/PIL

Benzylidene N-oxides, substituted O CH

Y

E-Structure RZtBu, YZH

N

R

(1) 67.7G1.6

283.1G6.5

(1) 68.7G1.2

287.6G5.1

(1) 68.3G1.9 (2) 63.3G0.7

285.9G7.9 264.9G3.0

4-MeO

(2) 63.9G1.5

267.3G6.4

4-iPr

(2) 63.9G1.5

267.5G6.1

2-OH

(2) 70.5G1.4

294.8G6.0

4-NO2 4-iPr RZPh, YZH

7366—CHAPTER 6—5/2/2007—11:18—JEBA—15362—XML MODEL B – pp. 255–368

(2) 1986KIR/ACR

BDEs of O–X Bonds

357

(3) 57.1G1.1

238.9G4.6

65.8G0.8

275.1G3.3

Derived

1989ACR/KIR

78.6G0.4

328.7G1.7

Review

2005ACR/PIL

73.3G3.1

306.6G13

Review

2005ACR/PIL

81.5G3.1

341.2G13

Review

2005ACR/PIL

(1) 62.8G0.8 (2) 73.9G0.9

262.8G3.3 309.4G3.6

(1) Derived (2) Review

(1) 1975PEP/LEB (2) 2005ACR/PIL

2-NO2

(2) 73.9G1.4

309.4G6.0

2-CH3

(2) 74.0G3.2

309.5G13.5

2-C2H5

(2) 73.9G2.6

309.4G10.7

2,4,6-(CH3)3

(2) 73.9G3.3

309.4G13.6

di-N-Oxides RN(O)aN(O)R RZtBu

(3) 2002LEB/CHI

2,3-Diazabicyclo[2.2.1]-hept2-ene N-oxide N N

O

4,4’-Dinitroazoxyfurazan NO2

O N

N O N

NO2

N

N O

N

4,4’-Diaminoazoxyfurazan NH2 N

N O N

NH2

O N

N O

N

di-N-Oxides

Y

O

O

N

N

YZY 0 ZH

Y'

(continued)

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Table 6.4 (continued) O–N BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Quinoline N-oxides, substituted O Y

8 7 6 5

N

1 2 43

YZ6-OCH3

64.3G1.2

269.2G5.0

Calorimetry

2003SIL/SAN

62.6 58.0

261.9 242.5

Combined

2004SIL/GOM

58.7 61.9

245.7 258.8

Combined

2004SIL/GOM

67.1G1.3

280.7G5.6

Calorimetry

1990LEI/PIL

2-Amino-3-quinoixalinecarbonitrile-1,4-dioxide O 2nd step

CN

1st step

NH2 O

2-Amino-3-quinoixalinecarbonitrile-1,4-dioxide 1st step

O CN NH2

2nd step

O

Phenazine N-oxide O N N

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BDEs of O–X Bonds

359

2-Hydroxyphenazine-di-Noxide O OH

N

61.4

256.9

Combined

2005GOM/SOU

65.2

273.0

Combined

2005GOM/SOU

62.2

260.2

Combined

2005GOM/SOU

65.6

274.6

Combined

2005GOM/SOU

(1) 58.2G1.9 (2) 59.1G1.8

243.5G7.9 247.2G7.7

(1) Calorimetry (2) Review

(1) 2002MAT/LEB(b) (2) 2005ACR/PIL

N O OH

N N O

2-Hydroxyphenazine-di-Noxide O

OH

N N O

2-Hydroxyphenazine-di-Noxide OH N N O

Benzo furoxans N N

O N

O N

N N

O

O

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.4 (continued) O–N BDEs

The broken bonds (boldfaceZdissociated atom or group) O

N

N

N

N

N

N

N

6.5

(1) 57.8G1.8 (2) 57.7G1.8

241.8G7.5 241.6G7.4

(1) 57.4G1.5 (2) 56.7G1.5

240.2G6.3 237.1G6.1

O

N

O

N

O

References

O

O N

kJ/mol

O

O

O

kcal/mol

Methods (reference in parentheses)

O

N

N

BDEs (boldfaceZ recommended data; reference in parentheses)

O

O–S bonds

Table 6.5 O–S BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Sulfur monoxide OaS

(1) 124.7 (2) 123.78G0.01 (3) 123.6G2.6

521.7 517.90G0.05 517.1G10.9

(1) Review (2) Spectroscopy (3) Spectroscopy

(1) 1970DAR (2) 1994CLE/COL (3) 2000RED/AHA

Oxythio radical O–SH

36.2

151.5

Derived from DfH0 in ref.

1993BAL/CAS

Sulfur dioxide OaSO

(1) 132G2 (2) 130.1G0.2, 0 K (3) 131.7

552.3G8.4 544.3G0.9 551.1

(1) Spectroscopy (2) Spectroscopy (3) Derived from DfH0 in ref.

(1) 1970DAR (2) 1971OKA (3) 1996NIST

Sulfur trioxide OaSO2

83.3

348.5

Derived

1978BEN

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BDEs of O–X Bonds

361

Disulfur oxide OaSS

103.8

434.3

Derived from DfH0 in ref.

1996NIST

Formylthio OaSH2

71G4

297.1G16.7

Derived

1978BEN

Fluoroformyl fluoride OaSF2

118.7

496.6

Derived from DfH0 in ref.

1996NIST

(1) 99G6 (1) 104G2 (2) 105

414G25 435.1G8 439.3

Derived

(1) 1978TAK

(1) 109G27 (2) 110G5 (3) 122.7 (4) 110.9

456G113 460G21 513.3 463.8

(1) Derived (2) Derived (3) MS (4) Derived from DfH0 in ref.

(1) 1978TAK (2) 1978BEN (3) 1996MIL/NES (4) 1996NIST

(1) 104G7

435G29

Derived

(1) 1978TAK

(1) 92G2 (2) 95

384.9G8 397.5

Sulfurous acid OaS(OH)2

118G6

493.7G25

Derived

1978BEN

Sulfur tetrafluorooxide OaSF4

102G6

426.8G25

Derived

1978BEN

Dimethyl sulfoxide OaS(CH3)2

86.6

362.3

Derived

1978BEN

Diethyl sulfoxide OaS(C2H5)2

88.7

371.1

Derived

1978BEN

Chloroformyl chloride OaSClx xZ1 2

Sulfuryl fluoride OaS(O)F2

Sulfuryl chloride OaS(O)Clx xZ1 2

(2) 1978BEN

(2) 1978BEN

(continued)

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Table 6.5 (continued) O–S BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Diphenyl sulfoxide OaS(C6H5)2

89.3

373.6

Derived

1978BEN

(Methoxysulfinyl)methoxy OaS(OMe)2

116G6

485.3G25

Derived

1978BEN

Dimethylsulfone OaS(O)(CH3)2

(1) 112 (2) 109.9G0.7

468.6 459.7G2.8

(1) Derived (2) Derived from DfH0 in ref.

(1) 1978BEN (2) 2005ACR/PIL

Diethylsulfone OaS(O)(C2H5)2

112

468.6

Derived

1978BEN

86

360.0

Calorimetry

2003ROU/TEM

112.3G3 112.3

470G12 470

Calorimetry

1988HER 2003ROU/TEM

Diphenylsulfone OaS(O)(C6H5)2

113

472.8

Derived

1978BEN

Phenylsulfone OaS(O)(C6H5)

109

456.1

Derived

1978BEN

Sulphuric acid OaS(O)(OH)2

110G3

460.2G12.6

Derived

1978BEN

Dimethoxy sulfate OaS(O)(OMe)2

108

451.9

Derived

1978BEN

Thian-1-one O

S

Thiane-1,1-dione O O

S

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BDEs of O–X Bonds

363

Diethoxy sulfate OaS(O)(OEt)2

109

456.1

Derived

1978BEN

Phenyl phenylsulfonyl sulfate OaS(O)(Ph)(PhSO2)

122

510.4

Derived

1978BEN

Phenyl phenylthiooxy sulfate OaS(O)(Ph)(PhSO)

122G3

510.4G12.6

Derived

1978BEN

Phenyl thiophenyl sulfate OaS(O)(Ph)(PhS)

115G4

481.2G16.7

Derived

1978BEN

Hydroxythiol HO–SH

70.1G4

293.3G16.7

Derived from DfH0 in ref.

1993OHA/DEP

Methylthio peroxy OO–SCH3

w11

w46

Pulse laser photolysis

1992TUR/BAR

Oxyhydrosulfide radicals HO–S

70G4

292.9G16.7

Derived

1978BEN

Oxyhydrodisulfide HO–S2

13.2G2

55.2G8.4

Derived from DfH0 in ref.

2003NASA/JPL

Sulfenic acid HO–SOH

74.9G3

313.4G12.6

Derived from DfH0 in ref.

1978BEN

Sulfuric acid HO–S(OH)O2

92.0G2

384.9G8.4

Derived from DfH0 in ref.

1998CHA

Adduct of OH and SCS HO–SCS

35.3G1.5

147.7G6.3

Derived from DfH0 in ref.

1990MUR/LOV

Methanesulfenic acid HO–SCH3

72.6G3

303.8G12.6

Derived from DfH0 in ref.

1996HUN/SHE

(continued)

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Table 6.5 (continued) O–S BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Adduct HO–S(CH3)2

w14

w59

Est. by exp.

1992STI/NIC

Adduct HO–S(CD3)2

(1) 10.1G1.1 (2) 10.7G2.5

42.3G4.6 44.8G10.5

LP/LIF

(1) 1995HYN/STO (2) 1996BAR/TUR

Methanesulfonic acid HO–SO2CH3

86.1G3

360.2G12.6

Derived from DfH0 in ref.

2000GUT/GAL

Hydrooxy methylsulfonate HOO–SO2CH3

116.8

488.7

Derived from DfH0 in ref.

1978BEN

Methoxy methylsulfonate CH3OO–SO2CH3

111.6

466.9

Derived from DfH0 in ref.

1978BEN

Methylthiyl peroxy CH3S–OO

w11

w46

Pulsed laser photolysis

1992TUR/BAR

w65

w272

MS

1965PAU/LUS

Methyoxy-1-thiol HS–OCH3

56G8

234G34

Est. by exp.

2000AMA/WIE

Methoxymethylthio CH3S–OCH3

53G10

222G42

Est. by exp.

2000AMA/WIE

N,N-difluorohydroxylamine O-Fluorosulfate FS(O2)–ONF2

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BDEs of O–X Bonds

6.6

365

O–halogen bonds

Table 6.6 O–Halogen BDEs

The broken bonds (boldfaceZdissociated atom or group) Hypofluorous acid F–OH

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

51.4

215.1

Derived from DfH0 in ref.

1998CHA

39.2

164.1

Derived from DfH0 in ref.

2003NASA/JPL

52.6

220.0

(1) 43.5G0.5 (2) 40.2G2.5

182.0G2.1 168.2G10.5

(1) 1968CZA/CAS (2) 1994SCH/WAL

(3) 48G1

200.8G4.2

(1) Pyrolysis (2) Derived from DfH0 in ref. (3) Re-evalated

(3) 2000REI/PRA

(1) %47.4G1.2, 0K (2) O47.0

%198G5

(1) PIMS

(1) 1991RUS/APP

O196.6

(2) Derived from DfH0 in ref.

(2) 1996NIST

(1) 18.4 (2) 11.68G0.5, 0K (3) 12.9G0.5

77.2 48.9G2.1

(1) MS (2) Spectrokinetic

(1) 1966MAL/MCG (2) 1987PAG/RAT

54.0G2.1

(3) Derived from DfH0 in ref.

(3) 2003NASA/JPL

Fluorine dioxide O–FO

K5G6

K21G25

Derived from DfH0 in ref.

2003NASA/JPL

Fluoronitrooxy F–ONO2

34.2

143.1

Derived from DfH0 in ref.

1998CHA

Hypochlorous acid Cl–OH

55.8

233.5

Derived from DfH0 in ref.

2003NASA/JPL

Difluorine monoxide F–OF –O

Trifluoromethyl hypofluorite F–OCF3

Methyl hypofluorite F–OCH3

Fluoro peroxy F–OO

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 6.6 (continued) O–Halogen BDEs

The broken bonds (boldfaceZdissociated atom or group) Dichlorine monoxide Cl–OCl

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 33.9

142

(1) Derived from DfH0 in ref.

(1) 2003NASA/JPL

(2) 64.20G0.03 (3) 64.3 (4) 63.93G0.02 (5) 74.9G2.3

268.61G0.13 268.9 267.47G0.08 313.6G9.6

(2) Spectroscopy (3) Review (4) Spectroscopy (5) Spectroscopy

(2) 1958DUR/RAM (3) 1991ABR/AZI (4) 1993MCL/PAR (5) 2001RAJ/FER

%220.9G8.4

PIMS

1997ASH/RUS

48.0

200.8

Derived from DfH0 in ref.

1994NIST

tert-Butyl hypochloride Cl–O-tert-C4H9

47.4

198.3

Derived

1968WAL/PAP

Chlorine dioxide O–ClO

(1) 59G3 (2) 59.1G0.1 (3) 61.3G0.3

246.9G12.6 247.3G0.5 256.3G1.3

(1) Pyrolysis (2) PD (3) Derived from DfH0 in ref.

(1) 1968CZA/CAS (2) 2001DEL/PAR (3) 2003NASA/JPL

Chloro peroxy Cl–OO

(1) 5.94G0.49 (2) 6.01G0.01 (3) 5.8G0.4 (4) 5.6G1

24.87G2.05 25.16G0.05 24.2G1.7 23.4G4.2

(1) Photolysis (2) Photolysis (3) UV abs. (4) Derived from DfH0 in ref.

(1) 1991NIC/KRE (2) 1991BAE/HIP (3) 1992MAU/BUR (4) 2003NASA/JPL

(5) 5.87G0.10

24.40G0.42

(5) Spectroscopy

(5) 2004SUM/SUM

Dichlorine dioxide Cl–OOCl

21.8

91.2

Derived from DfH0 in ref.

1994NIC/FRI

Dichlorine trioxide O–ClOOCl

59.2

247.7

Derived from DfH0 in ref.

1994NIC/FRI

–O

Trifluoromethyl hypochlorite %52.8G2 Cl–OCF3

Methyl hypochlorite Cl–OCH3

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BDEs of O–X Bonds

Chloro trioxide

367

17.1

71.5

Derived from DfH0 in ref.

1994NIC/FRI

47.0G2.3

196.7G9.5

Derived from DfH0 in ref.

2005ACR/PIL

Chloronitrooxy Cl–ONO2

41.1

172.0

Derived from DfH0 in ref.

1990AND/FAH

Hypobromous acid Br–OH

(1) 48.5G0.4 (2) 51G1 (3) 50.1G1

202.7G1.8 213.4G4.2 209.6G4.2

(1) PI (2) Review (3) Derived from DfH0 in ref.

(1) 1994RUS/BER(d) (2) 1999JUR (3) 2003NASA/JPL

(1) 29.9

125

(1) Derived from DfH0 in ref.

(1) 2003NASA/JPL

(2) 56.1G0.6 (3) 55.9G1.5 (4) 55.8G1.0 (5) 56.3G0.5 (6) 56.9G0.1

234.7G2.5 233.9G6.3 233.5G4.2 235.4G1.9 238.1G0.4

(2) Spectroscopy (3) Review (4) PD (5) Spectroscopy (6) PD

(2) 1958DUR/RAM (3) 1996ORL/TYN (4) 2002ZOU/KIM (5) 2004FLE/HAR (6) 2006KIM/DOO

tert-Butyl hypobromide Br–O-tert-C4H9

43.8

183.3

Derived

1968WAL/PAP

Bromine dioxide O–BrO

49.0G2

204.8G8.4

Derived from DfH0 in ref.

2003NASA/JPL

Bromo peroxy Br–OO

0.7G10

3.1G42

Derived from DfH0 in ref.

2003NASA/JPL

Bromo trioxide Br–O3

7.8

32.8

Derived from DfH0 in ref.

1994NIC/FRI

Bromonitrooxy Br–ONO2

34.2G1.5

143.1G6.3

Kinetics

1996ORL/TYN

Cl–O3

Chloro trioxide O2Cl–O

Dibromine oxide Br–OBr –O

(continued)

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Table 6.6 (continued) O–Halogen BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group) Hypoiodous acid I–OH

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

51.0

213.4

Derived from DfH0 in ref.

2001IUPC

(1) 31.1

130.1

(1) Derived from DfH0 in ref.

(1) 2003NASA/JPL

(1) 57.4 (2) 43G5 (3) 58G2

240.0 180G21 242.7G8.4

(2) Spectroscopy (3) Review

(2) 1958DUR/RAM (3) 1996ORL/TYN

Iodo peroxy I–OO

2.5G4

10.5G17

Derived from DfH0 in ref.

2003NASA/JPL

Iodo rioxide I–O3

1.6

6.7

Derived from DfH0 in ref.

1994NIC/FRI

Iodomonitrooxy I–ONO2

O33.6

O140.6

Review

1996ORL/TYN

63.2G1.9

264.5G8.1

Calorimetry

1999SIL/MAT

Diiodo oxide I–OI –O

2-Iodosobenzoic acid C(O)OH I

O

Note: (1) The BDEs in the clusters and complexes of C-, Si-, Ge-, Sn-, and Pb-ions are listed in Chapter 24. (2) The BDEs in the clusters and complexes of N-, P-, As-, Sb-, and Bi-ions are listed in Chapter 25. (3) The BDEs in the clusters and complexes of O-, S-, Se-, Te-, and Po-ions are listed in Chapter 26. (4) The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27.

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chapter seven

BDEs of N–X bonds 7.1 7.1.1

N–H bonds N–H bonds in non-anilines

Table 7.1.1 N–H BDEs in Non-Anilines BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) Ammonia H–NH2 DfH0(R)Z44.5G0.2 (186.2G1.0) H–NH DfH0(R)Z85.3G0.2 (357G1) H–N

kcal/mol (1) (2) (3) (4) (5)

108.2G0.3 107.57G0.06 108.5G0.3 107.6G0.1 97.6

(6) 79.3G3.7 (7) %81.0

kJ/mol 452.7G1.3 450.08G0.24 454.0G1.3 450.2G0.4 408.4

Methods (reference in parentheses)

References (1) (2) (3) (4) (5)

331.8G15.4 %338.9

(1) Recommended (2) Photolysis (3) GPA (4) Review (5) Derived from DfH0 in ref. (6) Spectroscopy (7) Spectroscopy

(1) Photolysis

(1) 1996MOR/DIX

Deuterated ammonias H–NHD

(1) 107.95G0.14

451.66G0.60

H–ND2

(1) 108.12G0.09

452.38G0.36

1994BER/ELL 1996MOR/ASH 2003REE/HAR 2003BLA/ELL 1996NIST

(6) 1968GAY (7) 1979HUB/HER

D–NHD

(1) 109.78G0.17

459.32G0.72

D–ND2

(1) 110.15G0.06

460.87G0.024

D–N

(2) 81.6

341.6

(2) Spectroscopy

(2) 1979HUB/HER

Difluoroamonia H–NF2 DfH0(R)Z10.1G2 (42.3G8)

75.7G2.5

316.7G10.5

Calorimetry

1969PAN/ZER

(1) 75G5 (2) 60.8

314G21 254.4

(1) Pyrolysis (2) Derived from DfH0 in ref.

(1) 1970LIK/SHI (2) 1996NIST

(Z)-diazene H–NNH DfH0(R)Z59.6 (249.5)

(continued)

369

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Comprehensive Handbook of Chemical Bond Energies

Table 7.1.1 (continued) N–H BDEs in Non-Anilines BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

Methods (reference in parentheses)

kcal/mol

kJ/mol

92G5 %93 92.7G3.1 %88.7G0.5 93.7

384.9G20.9 %389 387.9G13.0 % 371.1G2.1 392.0

(1) (2) (3) (4) (5)

Hydrazoic acid H–N3 DfH0(R)Z99.0G5 (414.2G20.9)

(1) (2) (3) (4) (5)

Methanimine H–NaCH2

(1) 85G5, at 0 K (2) 87G6

356G21 364G25

(1) PES (2) Derived

(1) 1991COW/TRA (2) 1994SUN/PAN

Nitrosyl hydride H–NO DfH0(R)Z21.58 (90.29)

(1) 49 (2) 48.1G0.1 (3) 47.7

205 201.2G0.4 199.5

(1) Kinetics (2) Spectrometry (3) Derived from DfH0 in ref.

(1) 1962HOL (2) 1996DIX (3) 1999AND

D–NO

(4) 49.9

208.7

(4) Spectrometry

(4) 1984DIX/ROS

Isocyanic acid H–NCO DfH0(R)Z28.9 (120.9)

(1) %111.5G1 (1) 110.5G3.8 (3) 110.1G0.5 (4) %109.6G0.4 (5) 110.3

%466.5G4 462.3G15.9 460.7G2.1 %458.6 G1.7 461.3

(1) PES (2) PIMS (3) Photodissociation (3) Photolysis (5) Derived

(1) (2) (3) (4) (5)

Iso-thiocyanic acid H–NCS

(1) 98G1 (2) 96G6 (3) %94.8G1.1

410G4 402G25 %396.6G4.6

(1) Photodissociation (2) PES (3) PIMS

(1) 1973LEN/MEL (2) 1993BRA/KIM (3) 1994RUS/BER(b)

Cyanoamino radical H–NCN

83G2

347.3G8.4

PES

1997CLI/WEN

Methylamine CH3NH2 DfH0(R)Z44.0G2 (184.1G8.4)

431.0G10.5 423.4G12.6 R425 425.1G8.4 418.4G10.5 w431

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

CH3ND2

(1) (2) (3) (4) (5) (3)

Tert-butylamine tert-BuNH2 DfH0(R)Z22.8G3 (95.4G12.6)

(1) 100 (2) 93.3G2 (2) 95G2

418.4 390.4G8.4 397.5G8.4

(1) AOP (2) PAC

103G2.5 101.2G3 R101.5 101.6G2 100.0G2.5 w103

ICR CL Correlation UV Photolysis AOP

References

VLPP AE IR CL Review Derived

7366—CHAPTER 7—3/2/2007—20:41—CRCPAG—15363—XML MODEL B – pp. 369–424

(1) (2) (3) (4) (5)

1981PEL/JAC 1987HAB/WAT 1993JEN 1999ZHA/XU 2002ALN/ZHA

1993BRA/KIM 1994RUS/BER(c) 1995ZHA/DUL 1996BRO/BER 2004JAN/ROS

1972GOL/SOL 1973SHA/FRA 1987WAT/SET 1988COL 1994SUN/PAN

(1) 1998BOR/LIU (2) 2002LAL/ALL

BDEs of N–X Bonds

371

Benzylamine C6H5CH2NH2 DfH0(R)Z68.9G3 (288.3G12.6)

100

418.4

AOP

1998BOR/LIU

1-Naphthanlenamine RNH2

89.6

374.7

Correlation

2000DEN/DEN

2-Naphthanlenamine RNH2

90.7

379.5

Correlation

2000DEN/DEN

Dimethylamine (CH3)2NH DfH0(R)Z37.8G2 (158.2G8.2)

(1) 95G2.5 (2) 94.6G2 (3) 91.5G2.0

397.5G10.5 395.8G8.4 382.8G10.5

(1) VLPP (2) Review (3) Derived

(1) 1972GOL/SOL (2) 1988COL (3) 1994SUN/PAN

Propylamine phosphonium bromide (n-PrNH-PCPh3) BrK

92.7

387.9

AOP

1995CHE/LIU

Methylnitroamine CH3NHNO2

84.3

352.8

Derived

2003MIR/KON

Nitro[(nitroamino)methyl]amine CH2(NHNO2)2

84.0

351.6

Derived

2003MIR/KON

Nitro[2-(nitroamino)ethyl]amine (CH2)2(NHNO2)2

84.0

351.6

Derived

2003MIR/KON

Nitro[5-(nitroamino) pentyl]-amine (CH2)6(NHNO2)2

83.2

348.2

Derived

2003MIR/KON

Hydrazine H–NHNH2 DfH0(R)Z58.2 (243.5)

(1) %85 %356 (2) 87.5 366.1 (3) 80.8G0.3, 0 K 338.1G1.3

(1) IR CL (2) Pyrolysis (3) PIMS

(1) 1973DUE/SET (2) 1988GRE/COL (3) 1991RUS/BER

Hydrazine radical H–N2H2

(1) 43.8G1.1, 0 K 183.3G4.6 (2) 44.8 187.4

(1) PIMS (2) Derived from DfH0 in ref.

(1) 1991RUS/BER (2) 1996NIST

(continued)

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372

Comprehensive Handbook of Chemical Bond Energies

Table 7.1.1 (continued) N–H BDEs in Non-Anilines BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Methylhydrazine H–NHNH(CH3)

(1) 88 (2) 66G5

368 276G21

(1) Pyrolysis (2) MS

(1) 1964EBE (2) 1970FON/HUD

Methylhydrazine radical HNN(CH3)–H

53G6

222G25

MS

1970FON/HUD

1,1-Dimethylhydrazine (CH3)2NNH2

(1) 88 (2) 85G5

368 356G21

(1) Pyrolysis (2) MS

(1) 1964EBE (2) 1970FON/HUD

Ethane-1,2-diamine H2NCH2CH2NH2

96.3

403.0

Derived

2003MIR/KON

Amonomethanenitrile NH2CN DfH0(R)Z76.3G0.7 (319.4G2.9)

(1) 99G3 (2) 96.6G2.6

414.2G12.6 404.2G10.9

(1) AOP (2) Derived from DfH0 in ref.

(1) 1990BOR/HAR(b) (2) 2001BIS/HOO

Urea (NH2)2CaO DfH0(R)Z0.2G3 (0.8G12.6)

111

464.4

AOP

1991BOR/JI(b)

Thiourea (NH2)2CaS DfH0(R)Z46.4G3 (194.1G12.6)

93

389.1

AOP

1991BOR/JI(b)

1-Aminoethane-1-thione CH3C(S)NH2

91

380.7

AOP

1991BOR/JI(b)

Aminophenylmethane-1-thione 91 PhC(S)NH2

380.7

AOP

1991BOR/JI(b)

Bis(phenylamino)methane1-thione (PhNH)2CaS

364.0

AOP

1991BOR/JI(b)

87

7366—CHAPTER 7—3/2/2007—20:41—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

373

Aminomethanamidine (NH2)2CaNH DfH0(R)Z59.9G3 (250.6G12.6)

104

435.1

AOP

1991BOR/JI(b)

Diphenylmethanimine Ph2CaNH

117

489.5

AOP

1991BOR/JI(b)

Benzylphenylthioamine C6H5CH2NHSPh

86.9

363.6

AOP

1998BOR/LIU

Hydroxylamine HONH2

81–82

339–341

Electrochemical

2006LIN/MER

Formamide HC(O)NH2 DfH0(R)Z11.9G3 (49.8G12.6)

108.5

454.0

AOP

1995BOR/ZHA

Acetamide 107.5 CH3C(O)NH2 DfH0(R)ZK1.6G3 (K6.7G12.6)

449.8

AOP

1991BOR/JI(b)

2-Ethyl-pentanamide Et3CC(O)NH2

109

456.1

AOP

1995BOR/ZHA

Tert-butanamide tert-BuC(O)NH2

109

456.1

AOP

1995BOR/ZHA

Benzamide PhC(O)NH2

107

447.7

AOP

1991BOR/JI

Methyl aminooate CH3OC(O)NH2

105

439.3

AOP

1997ZHA/BOR

Ethyl aminooate C2H5OC(O)NH2

105.3

440.6

AOP

1994ZHA/BOR(e)

(continued)

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374

Comprehensive Handbook of Chemical Bond Energies

Table 7.1.1 (continued) N–H BDEs in Non-Anilines BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

N-methylacetamide CH3C(O)NHMe

(1) 103.9 (2) 106.5

434.7 445.6

AOP

(1) 1990BOR/ZHA (2) 1995BOR/ZHA

N-(tert-butyl)-2,2-dimethyl propanamine tert-BuC(O)NHtBu

110.5

462.3

AOP

1995BOR/ZHA

Acetohydrazide MeC(O)NHNH2

82

343.1

AOP

1997ZHA/BOR

Benzenecarbohydrazide PhC(O)NHNH2

80.3

336.0

AOP

1997ZHA/BOR

Diacetamide (CH3C(O))2NH

107.5

449.8

AOP

1992BAU/DAV

Diuret (NH2C(O))2NH

108.5

454.0

AOP

1992BAU/DAV

Diacelhydrazine (NHC(O)CH3)2

91.5

382.8

AOP

1992BAU/DAV

Dibenzoylhydrazine (NHC(O)Ph)2

89.5

374.5

AOP

1992BAU/DAV

N-((1E)-buta-1,3-dienyl)benzamide PhC(O)NHPh

97

405.8

AOP

1991BOR/JI(b)

Benzenesulfonamide PhSO2NH2

105

439.3

AOP

1997ZHA/BOR

Hydrazinophenyl sulfone PhSO2NHNH2

81

338.9

AOP

1997ZHA/BOR

7366—CHAPTER 7—3/2/2007—20:41—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

375

Ethanamidine CH3C(aNH)NH2

102

426.8

AOP

1991BOR/JI(b)

Benzenecarboxamidine PhC(aNH)NH2

102

426.8

AOP

1991BOR/JI(b)

Diethyl(iminophenylmethyl)amine PhC(aNH)NEt2

119

497.9

AOP

1991BOR/JI(b)

((1Z)-2-aza-1,2-diphenyl-vinyl) phenylamine PhC(aNPh)NHPh

92

384.9

AOP

1991BOR/JI(b)

(((1Z)-2-aza-1,2-diphenylvinyl)amino)dimethylamine PhC(aNPh)NHNMe2

85

355.6

AOP

1991BOR/JI(b)

(Imino(phenylamino)methyl)phenylamine (PhNH)2CaNH

92

384.9

AOP

1991BOR/JI(b)

((((1E)-2-aza-1,2-diphenyl-vinyl) 84.7 amino)amino)-dimethylamine PhC(NHNMe2)aNPh

354.4

AOP

1992BOR/JI

(Tert-buytl)phenylthioamine tBuNHSPh

87.1

364.4

AOP

1998BOR/LIU

Phenyl-N-(phenylcarbonylamino)carboxamide PhC(O)NHNHC(O)Ph

89.3

373.6

AOP

1997ZHA/BOR

N–H bonds at site 1

101.5

424.5

Electron attach.

2004DEN/PTA

3

124.5

521.0

Uracil

H

H 6

5 4

O

N H

2 3

1 N

H

O

(continued)

7366—CHAPTER 7—3/2/2007—20:41—CRCPAG—15363—XML MODEL B – pp. 369–424

376

Comprehensive Handbook of Chemical Bond Energies

Table 7.1.1 (continued) N–H BDEs in Non-Anilines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

N-[(1E)-1-aza-2-phenylprop-1enyl]aminoamide, substituted

H

Y C

NN

C(O)NH2

Me YZH

91.7

383.5

p-Cl

92.4

386.4

p-Br

92.3

386.0

p-Me

91.4

382.3

p-MeO

91.0

380.6

p-CF3

92.7

387.7

p-CN

92.7

387.7

p-NO2

92.4

386.4

81.1

339.3

83.1 80

347.7 334.7

YZH

82.6

345.6

Br

83.0

347.3

MeO

81.6

341.4

CN

84.2

352.3

(1) 93.2 (2) 92.6

389.9 387.4

AOP

1994ZHA/HUA

AOP

1997ZHA/BOR

AOP

1998BOR/LIU

AOP

(1) 1998BOR/LIU (2) 1998CHE/XIA

Diphenyl(phenylamino)amine, substituted

H N

Y

NPh2

YZH 2,4-(NO2)2 2,4,6-(NO2)3

Phenylphenylthioamine, substituted SPh

Y

N

H

Phenyl(phenylsulfonyl)-amine, substituted

SO2Ph Y YZH

N

H

7366—CHAPTER 7—3/2/2007—20:41—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

377

Cl

(2) 93.8

392.5

Br

(1) 94.4

395.0

Me

(2) 91.7

383.7

MeO

(1) 89.1 (2) 89.0

372.8 372.4

CN

(1) 96.6

404.2

MeCO

(2) 95.2

398.3

NO2

(2) 97.1

406.3

86.1

360.2

Correlation

2000DEN/DEN

AOP

1997ZHA/BOR

AOP

1996STA/ZAR

Di-2-naphthamine (2-C10H7)2NH

Hydrazines, substituted

H N

NH2

Y YZH

72.6

303.8

p-Cl

73.0

305.4

p-Me

71.9

300.8

p-Et

76.3

319.2

p-CF3

77.9

325.9

p-CN

77.8

325.5

N-alkoxyanilines

NO2 R1

H N

OR

R2 R Me

R1 H

R2 NO2

75.4

315.3

Me

NO2

H

76.1

318.2

Me

NO2

NO2

77.6

324.8

i-Pr

NO2

NO2

78.0

326.2

Bis(1,1-dimethyl-1-silaethyl)amine H–N(SiMe3)2

110.9

464.0

Derived

1998BEC/WAL

N–H bond in (R,R)-[Rh(trop2dach)]C

86.8G1.2

363G5

Electrochemical

2005MAI/BRE

(continued)

7366—CHAPTER 7—3/2/2007—20:41—CRCPAG—15363—XML MODEL B – pp. 369–424

378

Comprehensive Handbook of Chemical Bond Energies

Table 7.1.1 (continued) N–H BDEs in Non-Anilines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) H–NHC%H2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

31.8G3

133.1G12.6

H–N(CH3)C H2

32.6G3

136.4G12.6

H–NHC%HCH3

31.4G3

131.4G12.6

%

7.1.2

Methods (reference in parentheses) Derived from DfH0 in ref

References 1996NIST

N–H bonds in anilines

Table 7.1.2 N–H BDEs in Anilines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) Aniline or benzenamine PhNH–H DfH0(R)Z58.4G1 (244.3G4.2)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) 88.0G2 (2) 92.3 (3) 89.1 (4) 92.2 in sol. (4) 89.7 in gas (5) 92.2

kJ/mol

Methods (reference in parentheses)

References

368.2G8.4 386.2 373 385.8 375.3 385.8

(1) VLPP (2) AOP (3) Electrochemical (4) PAC

(1) 1978COL/BEN (2) 1993BOR/ZHA (3) 1994JON/LIN (4) 1997MAC/WAY

(5) AOP

(5) 1997CHE/WAN

(3) 88.8 in gas 371.5 (3) 91.3 in sol. 382.0 (8) 92.9G2.1 388.7G8.8

(1) Electrochemical

(1) 1994JON/LIN

(2) Electrochemical

(2) 1995JON/LIN

(4) 93.1

(3) PAC

(3) 1997MAC/WAY

Anilines, mono-substituted NH

Y

YZ4-F

2-Cl

H

389.5

3-Cl

(4) 92.6

387.4

(4) AOP

(4) 1993BOR/ZHA

4-Cl

(4) 92.4 (7) 92.3

386.6 386.2

(5) AOP

(5) 1997ZHU/ZHA

(6) Correlation

(6) 2000DEN/DEN

3-Br

(4) 93.2

389.9 (7) AOP

(7) 1997CHE/WAN

4-Br

(4) 92.3 (7) 92.2

386.2 385.8

(8) GPA

(8) 2003REE/HAR

4-I

(1) 89.1

373

(9) Correlation

(9) 2005DEN/TUM

2-CN

(4) 95.1

397.9

3-CN

(4) 94.1

393.7

4-CN

(1) 91.8 (4) 95.2

384 398.3

7366—CHAPTER 7—3/2/2007—20:41—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

379 (7) 95.1 (9) 92.3

397.9 386.3

2-CF3

(2) 92.5 (9) 93.0

387 389.3

3-CF3

(2) (4) (5) (9)

93.2 95.7 96.6 93.8

390 400.4 404.2 392.3

4-CF3

(1) (4) (7) (9)

92.0 96.5 96.4 92.6

385 403.8 403.4 387.3

2-CH3

(2) 90.6 (9) 86.4

379 361.3

4-CH3

(1) 88.7 (3) 87.5 in gas (3) 90.0 in sol. (4) 92.0 (7) 91.9

371 366.1 376.6 384.9 384.6

4-NH2

(1) 86.0 (9) 86.6

360 362.3

4-NO2

(4) 96.7

404.6

4-tert-Bu

(1) 88.9 (6) 92.2 (9) 89.5

372 385.6 374.3

4-CH3CO

(1) (4) (6) (9)

90.6 94.2 93.8 91.1

379 394.1 392.6 381.3

2-CH3O

(2) 88.7 (4) 90.4 (9) 89.2

371.0 378.2 373.3

3-CH3O

(4) 93.9

392.9

4-CH3O

(1) 87.2 (7) 90.3 (9) 87.8

365 377.9 367.3

3-CF3SO2

(4) 95.7

400.4

(2) 88.0 (9) 88.5

368 370.3

3,4-Me2

(2) 88.7 (9) 89.2

371 373.3

3,5-Me2

(2) 90.3 (9) 90.9

378 380.3

2,4-(MeO)2

(2) 87.7 (9) 88.3

367 369.3

3,4-(MeO)2

(2) 88.4

370

Anilines, di-and trisubstituted 2,4-Me2

(2) Electrochemical

(2) 1995JON/LIN

(4) AOP

(4) 1993BOR/ZHA

(9) Correlation

(9) 2005DEN/TUM

(continued)

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380

Comprehensive Handbook of Chemical Bond Energies

Table 7.1.2 (continued) N–H BDEs in Anilines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(9) 89.0

372.3

3,5-(MeO)2

(2) 91.5 (9) 92.1

383 385.3

3,5(CF3)2

(4) 97.2

406.7

2-NO2K4-Cl

(4) 97.6

408.4

3-NO2-4-Cl 2,4,6-Cl3

(4) 97.6 (4) 95.5

408.4 399.6

Methods (reference in parentheses)

References

Phenylhydroxylamine N Y

OH

H

YZH

69.8

292

p-Me

67.9

284

AOP

1998CHE/LU

p-Br

72.4

303

N-methyl-phenylamine PhNHMe DfH0(R)Z57.6G1.5 (241.0G6.3)

(1) 89.3 (2) 87.5G2 (3) 91.9

373.6 366.1G8.4 384.5

(1) AOP (2) VLPP (3) Correlation

(1) 1993BOR/ZHA (2) 1978COL/BEN (3) 2000DEN/DEN

Phenyl-1-naphthlamine 1-C10H7NHC6H5

85.3

357.1

Correlation

2000DEN/DEN

Phenyl-2-naphthlamine 2-C10H7NHC6H5

86.7

362.9

Correlation

2000DEN/DEN

4-Methoxy-N-phenylbenzenamine 4-CH3OC6H4NHPh

85.1

355.9

Correlation

2000DEN/DEN

N-(4-phenoxy)phenyl2-naphthalenamine 2-C10H7NHC6H4(4 0 -C6H5O)

83.5

349.5

Correlation

2000DEN/DEN

7366—CHAPTER 7—3/2/2007—20:41—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

381

Alkyloxy(2-nitrophenyl)amine R6

H N OR NO 2

R4

R Me

R4 H

R6 NO2

75.4

315.5

Me

NO2

H

76.1

318.4

Me

NO2

NO2

77.6

324.7

iPr

NO2

NO2

78.0

326.4

(1) 98.9 (3) 99.5

413.8 416.3

p-Cl

(2) 98.7

413.0

p-Br

(2) 99.1

414.6

p-Me

(2) 97.1

406.3

p-MeO

(2) 95.3

398.7

p-MeCO

(2) 100.0

418.4

p-CF3

(2) 101.6

425.1

p-CN

(2) 101.1 (2) 101.5

423.0 424.7

p-NO2

(2) 102.0

426.8

92.7

387.9

p-Cl

93.4

390.8

p-Br

93.5

391.2

p-I

93.4

390.8

p-Me

91.8

384.1

p-MeO

90.4

378.2

p-MeCO

94.9

397.1

p-NO2

96.4

403.3

AOP

1996STA/ZAR

AOP

(1) 1993BOR/ZHA(b)

N-phenylacetamide, substituted COCH3 Y

N

H

YZH

(2) 1993CHE/ZHA (3) 1991BOR/JI

N-phenylacetamide, substituted CONMe2 N

Y

YZH

H

AOP

1998CHE/XIA

(continued)

7366—CHAPTER 7—3/2/2007—20:41—CRCPAG—15363—XML MODEL B – pp. 369–424

382

Comprehensive Handbook of Chemical Bond Energies

Table 7.1.2 (continued) N–H BDEs in Anilines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Diethyl(phenylamino)phosphino-1-one, substituted PhNHPO(OEt)2 PO(OEt)2

N

Y

H

YZH

(1) 94.7 (2) 94.9

396.2 397

AOP

(1) 1991BOR/ZHA (2) 1998CHE/LU

p-Cl

(3) 95.7

400.4

p-Br p-Me

(3) 95.7 (2) 93.5

400.4 391

p-MeCO

(2) 97.3

407

p-CN

(2) 98.9

414

p-NO2

(2) 100.6

421

84.5

353.4

Correlation

2004VAR

65.4

273.6

Correlation

2004VAR

N,N 0 -diphenyl-1,4-phenylenediamine Ph-NH-C6H4-NH-Ph

83.3G0.3

348.7G1.4

Correlation

2004VAR/KRI

N,N 0 -diphenyl-1,4-phenylenediamine radical Ph-NH-C6H4-N%-Ph

65.7G0.8

274.7G3.3

Correlation

2004VAR/KRI

Phenyl(phenylsulfonyl)amine PhNHSO2Ph

93.2

389.9

AOP

1998BOR/LIU

(3) 1998CHE/XIA

4-Hydroxydiphenylamine H p-HO

N

4-Phenylaminyl phenoxyl radical H p-O

N

7366—CHAPTER 7—3/2/2007—20:41—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

383

Phenyl-N-benzamide PhNHC(O)Ph

97.3

407.1

AOP

1993CHE/ZHA

(Dimethylamino)-N-benzamide PhNHC(O)NMe2

92.7

387.9

AOP

1998CHE/XIA

2,2,2-Trifluoro-N-phenylacetamide PhNHC(O)CF3

99.6

416.7

AOP

1993ZHA/BOR(b)

Phenylphenylthioamine PhNHSPh

82.6

345.6

AOP

1998BOR/LIU

Phenyl(phenylamino) methane-1-thione PhNHSOPh

90.2

377.4

AOP

1998BOR/LIU

(1) 72.9

305.1

AOP

(1) 1997CHE/WAN

(1) 73.2

306.4

Phenylhydrazine N

Y

XZH

NH2 H

p-Cl p-Me

(1) 72.2

302.2

p-CF3

(1) 78.3

327.3

p-CN

(1) 78.1 (2) 77.9

326.9 326

p-EtC(O)O

(1) 76.6

320.6

(1) 92.8 (2) 92.7

388.3 388

nBu

(1) 91.8

384.1

CH2Ph

(1) 89.3

373.7

(1) 81.9

342.8

Aminotriphenylphosphonium bromides X-NHCPPh3BrK XZnPr

(2) 1998CHE/LU

AOP

(1) 1995CHE/LIU (2) 1998CHE/LU

AOP

(1) 1995CHE/LIU

Aniline phosphonium bromide, substituted P+Ph3 BrN Y YZH

H

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 7.1.2 (continued) N–H BDEs in Anilines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(2) 68.4

286

p-Cl

(1) 81.9

342.8

p-Me

(1) 83.1 (2) 68.8

347.8 288

Methods (reference in parentheses)

References (2) 1998CHE/LU

p-CN

(2) 64.8

271

p-CF3

(2) 64.5

270

N-(phenylamino)acetamide PhNHNHC(O)Me

78.6

328.9

AOP

1997ZHA/BOR

1,2-Diphenylhydrazine PhNHNHPh

(1) 73.1 (2) 69.3

305.9 290.0

(1) FT-ICR (2) AOP

(1) 1991ING/FOK (2) 1997ZHA/BOR

Diphenylamine Ph2N–H DfH0(R)Z87.5G1.5 (366.1G6.3)

(1) 87.3 (2) 85.8G0.7 (3) 89.2, in sol. (3) 87.2, in gas (4) 87.2 (5) 87.5

365.3 359.0 373.2 364.8 364.7 366.1

(1) Kinetics (2) EPR (3) PAC

(1) 1987VAR/DEN (2) 1999LUC/PED (3) 1997MAC/WAY

(4) Correlation (5) AOP

(4) 2000DEN/DEN (5) 2002ALN/ZHA

(1) 88.4

369.9

(1) AOP

(1) 1993BOR/ZHA

(4) Correlation

(4) 2005DEN/TUM

(2) AOP

(2) 1994ZHA/BOR

(3) AOP

(3) 1991BOR/ZHA

Diphenylamine, substituted Ph N Y YZm-Cl

H

p-Me

(1) 86.9

363.6

m-Me

(1) 87.6

366.5

p-OH

(4) 84.5

353.4

p-MeO

(1) 85.6 (4) 84.4

358.2 353.3

p-tert-Bu

(4) 86.0 (4) 86.4

360.0 361.6

p-PhNH

(1) 79.2 (2) 79.9

331.4 334.3

p-NO2

(1) 90.4 (3) 91.0 (4) 90.5

378.2 380.7 378.8

p-tert-Bu

(4) 86.1

360.3

p-O%

(4) 65.4

273.6

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BDEs of N–X Bonds

385

Diphenylamine, substituted H N

Y YZp-Br

Y

(1) 88.1 (2) 87.0

368.6 364.2

(2) 85.4 (3) 86.3, in sol. (3) 86.2, in gas (4) 83.3 (5) 85.4

357.5 361.1 360.7 348.5 357.5

p-MeO

(1) 84.2 (2) 83.3 (4) 81.8 (5) 81.9

352.3 348.6 342.2 342.5

p-tert-Bu

(2) 85.8 (5) 84.9

358.8 355.1

p-N(CH3)2

(4) 79.5

332.6

89.6

374.7

84.2

352.5

84.2

352.1

84.3

p-Me

(1) AOP (2) Correlation

(1) 1993BOR/ZHA (2) 2000DEN/DEN

(3) PAC

(3) 1997MAC/WAY

(4) EPR (5) Correlation

(4) 2002PRA/DIL (5) 2005DEN/TUM

Correlation

2005DEN/TUM

352.8

Correlation

2005DEN/TUM

90.7

379.5

Correlation

2005DEN/TUM

84.6 83.5

353.9 349.5

1-Naphthylamine H N

X1

X2 X2ZH

X1ZH H

Ph

t-Bu

p-t-Bu-C6H4

Naphthylphenylamine H N

2-Naphthylphenylamines, substituted H N

XZH Ph C6H4-p-OPh

X

(continued)

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Table 7.1.2 (continued) N–H BDEs in Anilines

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Di(2-naphthyl)amine H N

86.2

360.5

Correlation

2005DEN/TUM

82.4

344.9

Correlation

2000DEN/DEN

N,N 0 -di(4-isopropylphenyl-)p-phenylendiamine 4-tBu-C6H4NH-4C6H4NHC6H4-t-Bu

79.7

333.6

Correlation

2000DEN/DEN

N,N 0 -di-2-naphthylp-phenylendiamine 4-(2-C10H7NH) C6H4NH-2 0 -C10H7

82.8

346.6

Correlation

2000DEN/DEN

84.2

352.2

Correlation

2005DEN/TUM

NK1-(3,7-bis(1,1-dimethyl-ethyl) napthalenyl)-benzenamine 1-(3,7-tBu2-C10H5)NHPh

p-Phenyl-endiamines, substituted H

H N

N

X2 X1 X1Zn-C8H17 X2Zn-C8H17

Ph

iso-Pr

81.3

340.2

Ph

Ph

82.9

346.9

Naphthyl

naphthyl

82.8

346.6

9H-carbazole 1,2-C6H4NH-1 0 ,2 0 -C6H4

88.8

371.6

Correlation

2000DEN/DEN

4-(1,1-Dimethylethyl)N-(4-(1,1-dimethylethyl) phenyl)-1-naphthalenamine 1(NHC6H4-4tBu)-4 0 -BuC10H6

84.2

352.1

Correlation

2000DEN/DEN

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BDEs of N–X Bonds

7.1.3

387

N–H bonds in cyclic compounds

Table 7.1.3 N–H BDEs in Cyclic Compounds

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1,2-Diaziridine

N N H

H

Pyrrole

4 5 1N 3 2

H

DfH0(R)Z70.8G3 (296.2G12.6)

88G4

368.2G16.7

GPA

1999BRO/KAS(b)

(1) 99G6 (2) 97 (3) 97G2 (4) 92.6G1.1 (5) 93.9G0.1

414.2G25.1 405.8 405.8G8.4 387.6G4.8 393.0G0.5

(1) Photodetach. (2) AOP (3) Derived (4) Photofrag. (5) PES

(1) 1975RIC/STE (2) 1991BOR/JI(b) (3) 1994SUN/PAN (4) 2003WEI/KUC (5) 2004GIA/ICH

87.3G0.3, at 0 K

365.2G1.2

Photofrag.

2006CRO/NIX

107

447.7

AOP

1995BOR/ZHA

105.8

442.7

AOP

1994ZHA/BOR(e)

105.7

442.2

AOP

1994ZHA/BOR(e)

2,5-Dimethylpyrrole

CH3 45 3 21N

H

CH3

2-Pyrrolidone

O 3 2 1N 4 5

H

1,3-Oxazolidin-2-one

O O3 2 1 4 5 N

H

4-Benzyl-1,3-oxazolidin-2-one

O

PhCH2

O3 2 4 51N

H

(continued)

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388

Comprehensive Handbook of Chemical Bond Energies

Table 7.1.3 (continued) N–H BDEs in Cyclic Compounds

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1,3-Oxazolin-2-one

O O3 2 4 1N 5

91.0

380.7

AOP

1994ZHA/BOR(e)

73.9

309.2

AOP

1997ZHA/BOR

(1) 91.7 (2) 92.5 (3) 118G3

383.7 387.0 493.7

(1) AOP (2) AOP (3) Electrochemical

(1) 1992ARN/VEN (3) 1992BAU/DAV (3) 1993LIN/JON

92.5

387.0

AOP

1992BAU/DAV

92.5

387.0

95.1G0.5

397.9G2.1

GPA

2005GIA/ICH

106.4G0.4

445.2G1.7

GPA

2006GIA/ICH

H

1-Phenylpyrazolidin-3-one

H O

Ph

N 3 2 1N 4 5

Succinimide H

O

O

N

Hydantoin, substituted H

O

N

O

N X XZH CH3

Imidazole

H N

N

H

H

H

Pyrazole

H H 1N 2 N

H

H DfH0(R)Z98.7G0.5 (413.0G2.1)

7366—CHAPTER 7—3/2/2007—20:42—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

389

2,4,5-Triphenylimidazole

Ph N

N

Ph

H

89.5

374.5

AOP

1994ZHA/BOR

82.5

345.2

AOP

1992BAU/DAV

78.5

328.4

AOP

1992BAU/DAV

Ph

4,4-Dimethylpyrazolidine-3,5dione

CH3 O

CH3 O

4 5 1 2 3 N N H

H

Urazole, 4-substituted X

O

N O 4 5 1 2 3 N N H

H XZ4-CH3 4-Ph

78.5

328.4

4-(p-MeOC6H4)

78.5

328.4

4-(p-MeC6H4)

78.5

328.4

4-(p-ClC6H4)

78.5

328.4

4-(m-ClC6H4)

79.5

332.7

94.5

395.4

AOP

1992BAU/DAV

87.6G4

366.5G17

PAC

2002LAL/ALL

1,2-Dimethylurazole

H O

N

O

N N CH3

CH3

2,2,6,6-Tetramethylpiperidine

CH3 CH3 N H CH3 CH3 Aminopyridine N H 6 12 NH 5 4 3

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 7.1.3 (continued) N–H BDEs in Cyclic Compounds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

H–N at site 2

87

364.0

3

94

393.3

4

84

351.5

109.5

458.1

91

380.7

(1) 115G3

481.2

(2) 104.5

437.2

XZO

98

410.0

S

81

338.9

XZO

99

414.2

S

82

343.1

Methods (reference in parentheses)

References

AOP

1993BOR/SIN

AOP

1995BOR/ZHA

Electrochemical

(1) 1998LIN/MER

2-Piperidone, analogues

65 N1 4 2 3

H

XZO

X

S

2,6-Piperidione

O 6 5 N 1 4 2 3

H

X X

O XZH CH3

(2) 1992BAU/DAV

2-Pyridone, analogues

6 5 N 1 4 2 3

H

X AOP

1993BOR/SIN

AOP

1993BOR/SIN

4-Pyridone, analogues

6 5 N 1 4 2 3

H

X

7366—CHAPTER 7—3/2/2007—20:42—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

391

1,2,4,5-Tetrahydropyridazine-3,6dione

H N NH

O

87.7

366.9

AOP

1997ZHA/BOR

AOP

2000CHE/LU

O

1,4-Dihydropyridine, substituted

X

H

EtCO2

N

CH3

CO2Et CH3

H

XZH

86.2

360.7

i-Pr

89.4

374.0

Ph

90.8

379.9

4-MeOC6H4

90.5

378.7

4-MeC6H4

90.6

379.1

4-ClC6H4

91.2

381.6

4-CNC6H4

92.8

388.3

94.8

396.6

AOP

1994ZHA/BOR(e)

89.1

372.8

AOP

1992ARN/VEN

77.7

325.1

AOP

1997ZHA/BOR

(1) 90.8 (2) 94.1

380 393.7

(1) Electrochemical (2) AOP

(1) 1994JON/LIN (2) 2000ZHU/HE

3-Hydrobenzoxazol-2-one

O 3 2 1 N

O

H Phthalimide

O N

H

O 1H-2-hydroindazol-3-one

O

NH

N

H

Indole

H N

(continued)

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Table 7.1.3 (continued) N–H BDEs in Cyclic Compounds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Adenine NH2

N

N

N

N

93.9G4.8

393G20

Mol. beam

2004ZIE/ROT

101

422.6

AOP

1993BOR/SIN

83

347.3

86.8

363.2

AOP

1997ZHA/BOR

85.9

359.5

Correlation

2005DEN/TUM

(1) 92.7 (2) 93.6

387.9 391.6

(1) AOP (2) AOP

(1) 1991BOR/ZHA (2) 1992ARN/VEN

H 2-Quinolone, analogues

H X

N

XZO S

2,3-Dihydrophthalazine-1,4-dione O

NH N H O 2,2,4-Trimethyl-1,2,3,4tetrahydroquinoline H

Me

N

Me Me Carbazole

H N 9

6

3

X X XZH DfH0(R)Z91.6G2 (383.3G8.4)

7366—CHAPTER 7—3/2/2007—20:42—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

393

(3) 93.0 (4) 88.8

389.1 371.6

(3) AOP (4) Correlation

(3) 2000ZHU/HE (4) 2000DEN/DEN

(1) 93.6 (2) 94.3 (3) 93.8

391.6 394.6 392.5

XZO

(1) 79.7 (2) 77.2G0.3 (3) 80.0

333.5 323.0G1.3 334.7

(1) AOP (2) EPR (3) AOP

(1) 1993BOR/ZHA (2) 1999LUC/PED (3) 2000ZHU/HE

S

(1) 82.3 (2) 79.3G0.3

344.3 331.8G1.3

Se

(2) 80.4G0.4

336.4G1.7

(1) 84.6 (2) 85.3 (3) 82.4G0.5 (4) 84.8

354.0 356.9 344.8G2.1 354.8

(1) AOP (2) AOP (3) EPR (4) AOP

(1) 1991BOR/CHE (2) 1994ZHA/BOR (3) 1999LUC/PED (4) 2000ZHU/HE

(1) 87.0 (2) 87.2

(1) 364.0 (2) 364.8

AOP

(1) 1991BOR/ZHA (2) 2000ZHU/HE

R1 H R1ZR9Z Me, R3ZR7ZH

77.7G0.4

325.1G1.7

EPR

1999LUC/PED

R1ZR9ZH, R3ZR7ZOMe

76.2G0.3

318.8G1.3

R1ZR9ZH, R3ZR7ZCMe3

78.1G0.4

326.8G1.7

R1ZR9ZH, R3ZR7ZCl

79.8G0.4

333.9G1.7

R1ZR9ZH, R3ZR7ZNO2

81.0G1.0

338.9G4.2

Br 3,6-dibromocarbazole

Phenothiazine, analogues

H N X

Iminostilbene, or 5Hdibenzo(b,f)azepine H

N

5H,10H,11H-dibenzo(b,f)azepine

H N

Phenothioazine, substituted R7 R3 S

N R9

(continued)

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Table 7.1.3 (continued) N–H BDEs in Cyclic Compounds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

2-Spirocyclo-hexyl-4-(spirotetrahydrofuran-2)-1,2,3,4tetrahydroquinoline H N

86.2

360.8

Correlation

2000DEN/DEN

ESR

1989MIS/POL

NMR

1999ROT/MAY

O

2,6-Diaryl-4-phenyl-1,2,3,4tetrahydro-sym-tetrazines H R1

N N R2

N N

R1ZH

R2ZH

H H

69.6

291

MeO Me

70.0 69.8

293 292 289

H

Cl

69.1

H

NO2

68.1

285

MeO

H

68.4

286

Me

H

68.8

288

Cl

H

70.3

294

NO2

H

72.9

305

MeO

NO2

67.2

281

NO2

MeO

73.4

307

76G2

318.0G8.4

N–H bond in FeII(H2bim) H2bimZ2,2 0 -bi-imidazoline 2+

HN HN N N HN

N N Fe(II) N

N

N H NH

HN

7366—CHAPTER 7—3/2/2007—20:43—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

395

N–H bond in CoII(H2bim) H2bimZ2,2 0 -bi-imidazoline 2+ HN

HN N N HN

N N Co(II) N

N

N H

72G3

301.2G12.6

NMR

2001ROT/YOD

71G1

297.1G4.2

NMR

2001ROT/YOD

86.3G0.5

361G2

Electrochemical

2005BUT/GEI

Methods (reference in parentheses)

References

NH

HN

N–H bond in FII(H2bip) H2bipZ2,2 0 -bi(tetrahydro) pyrimidine

2+

HN HN

N N

Fe(II) N N

N HN

N

N

H

NH

HN

N–H bond in Rh(I) [Rh(trop2NH)(bipy)]C tropZ5-H-dibenzo[a,d]cycloheptene-5-yl bipyZ2,2 0 -bipyridyl

7.2

N–N bonds

Table 7.2 N–N BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Nitrogen NbN

(1) 225.94G0.14 (2) 225.82G0.02

945.33G0.59 (1) Spectroscopy 944.84G0.10 (2) PD

(1) 1979HUB/HER (2) 2005TAN/HOU

Nitrogen anion NK–N (also see Chapter 25)

182.9

765.1

Derived

1979HUB/HER

Nitrogen cation NC–N (also see Chapter 25)

201.8

844.3

Derived

1979HUB/HER

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 7.2 (continued) N–N BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated group)

kcal/mol

kJ/mol

(1) K0.7G2.3

K2.9G9.6

(2) 6.2G1.8, 0 K

Azide cation NC–N2 (also see Chapter 25)

Nitrogen dimer cation

Azide radical N–N2

Methods (reference in parentheses)

References

26.1G7.7

(1) Derived from DfH0 in ref. (2) CID

(2) 1995MAY/FRY

86.2G1.8, 0K

360.8G7.7

CID

1995MAY/FRY

(1) 22.8 (2) 24.4 (3) 26.2G1.8 (4) 25.1G1.4 (5) 25.8G1.5

95.4 102.1 109.6G7.5 105.2G5.8 107.9G6.3

(1) HP MS (2) MS (3) AE (4) CID (5) HP MS

(1) 1970PAY/KEB (2) 1973TEN/CON (3) 1989NOR/LUO (4) 1991SCH/ARM (5) 1994HIR/YAM

Hydrogen azide HN–N2

15

63

Derived from DfH0 in ref.

2002CRC

Dinitrogen oxide ON–N

114.9G0.1

480.7G0.4

Derived from DfH0 in ref.

1996NIST

Nitric oxide dimmer ON–NO

2.03G0.03

8.49G0.12

PD

2003POT/DRI

Dinitrogen trioxide ON–NO2

10.2

42.5

Derived from DfH0 in ref.

1996NIST

Dinitrogen tetroxide O2N–NO2

13.7G0.2

57.3G1

Derived from DfH0 in ref.

2001IUPAC

Diazene HNaNH

(1) %123.8G1.1, 0K (2) 119.7

%518G5

(1) PIMS

(1) 1991RUS/BER

501

(2) Derived from DfH0 in ref.

(2) 1998CHA

(1) 65.5G0.4 (2) 66.2G0.3

274.1G1.7 277.0G1.3

(1) PIMS (2) Derived from DfH0 in ref.

(1) 1991RUS/BER (2) 2002CRC

NC 2 –N2 (also see Chapter 25)

Hydrazine H2N–NH2

7366—CHAPTER 7—3/2/2007—20:43—CRCPAG—15363—XML MODEL B – pp. 369–424

(1) 1993CON/CYR

BDEs of N–X Bonds

397

Dinitrogen difluororide (E)-FNaNF

80.6

337.2

Derived from DfH0 in ref.

1996NIST

Dinitrogen difluororide (Z)-FNaNF

83.6

349.8

Derived from DfH0 in ref.

1996NIST

Tetrafluorohydrazine F2N–NF2

(1) 21.5G1.6 (2) 21G1 (3) 21.6G0.5 (4) 22.2G3

90.0G6.7 87.9G4.2 90.4G1.9 92.9G12.6

(1) AP (2) Calorimetry (3) Derived (4) Derived from DfH0 in ref.

(1) 1961HER/DIB (2) 1969PAN/ZER (3) 1985BER/GRE (4) 1998CHA

Methylhydrazine NH2–NHCH3

(1) 67 (2) 65.9G2

280 275.8G8.4

(1) Pyrolysis (2) Derived from DfH0 in ref.

(1) 1964EBE (2) 1986PED/NAY

1,1-Dimethylhydrazine NH2–N(CH3)2

62.1G2

259.8G8.4

Derived from DfH0 in ref.

2002CRC

Phenylhydrazine NH2–NHC6H5

54.4G2

227.6G8.4

Derived from DfH0 in ref.

1986PED/NAY

1,2-Dimethylhydrazine (CH3)NH–NH(CH3)

66.0G3

276.1G12.6

Derived from DfH0 in ref.

2002CRC

Dimethyl(methylamino)amine (CH3)2N–NH(CH3)

60.8

254.4

Derived from DfH0 in ref.

1988LIA/BAR

Tetramethylhydrazine (CH3)2N–N(CH3)2

59.6

249.4

Derived from DfH0 in ref.

1994NIST

[(Dimethylamino)diazenyl] dimethyl-anine (CH3)2N–NNN(CH3)2

16.5

69

Kinetics

1961GOW/JON

1,2-Diphenyl hydrazine PhNH–NHPh

38.8G2

162.3G8.4

Derived from DfH0 in ref.

1994NIST

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 7.2 (continued) N–N BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated group) Nitroamine H2N–NO2

kcal/mol

kJ/mol

(1) 58.6

245.2

(2) 55.0

N-nitromethylamine CH3HN–NO2

N-nitrodimethylamine (CH3)2N–NO2

Methods (reference in parentheses)

References (1) 1991GUR/VEY

230.0

(1) Derived from DfH0 in ref. (2) Derived

50

209.2

Derived

2000KOS/MIR

(1) 43.8

183.3

(1) 1986PED/NAY

(2) 39.6 (3) 41.5G2.5

165.7 173.7G10.5

(1) Derived from DfH0 in ref. (2) Derived (3) Derived from DfH0 in ref.

1,1-Dinitroethane CH3N(NO2)–NO2

(1) 27.6 (2) 28.3

115.6 118.4

(1) Pyrolysis (2) Calorimetry

(1) 1975MAT/NAS (2) 1987MIR/KOR

1,1-Dinitropropane C2H5N(NO2)–NO2

29.0

121.5

Pyrolysis

1975MAT/NAS

1,1-Dinitrobutane C3H7N(NO2)–NO2

31.0

129.7

Pyrolysis

1975MAT/NAS

1,1-Dinitropentane C4H9N(NO2)–NO2

29.6

123.8

Pyrolysis

1975MAT/NAS

Methyl((methylnitroamino)methyl)nitroamine CH3N(NO2)CH2N(CH3)–NO2

40.0

167.4

Derived

2000KOS/MIR

Nitrozoamines ((NO2)3CCH2)2N–NO2

40.0

167.4

Derived

2001MIR/KOS

(H(NO2)2CCH2)2N–NO2

45.5

190.4

(NO2)3CCH2N((CH2)2C(NO2)3)– 40.0 NO2

167.4

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(2) 2000KOS/MIR

(2) 2000KOS/MIR (3) 2004KOS/MIR

BDEs of N–X Bonds

399

((NO2)3CCH2N(NO2) CH2CH2N-C(NO2)3)–NO2

40.0

167.4

(H(NO2)2CCH2N(NO2) CH2CH2N-CH(NO2)2)–NO2

40.0

167.4

((NO2)3CCH2)2N–NO2

39.0

163.2

((NO2)3CCH2N(NO)CH2CH2N- 40.0 C(NO2)3)–NO

167.4

Aminomethylnitrosoamino H2NN(CH3)–NO

42.9

179.6

Derived

1998LEB/CHI

Electrochemical

1998CHE/WAN

Electrochemical

2005ZHO/HAO

AOP

1998CHE/XIA

N-nitroso-acetanilides

O Y

N

CH3

N YZH

O

38.3

160.2

p-Cl

37.6

157.3

p-CH3

36.1

151.0

p-OCH3

43.8

183.3

p-NO2

39.2

164.0

N-methyl-nitrosobenzenesul forn-amides, substituted

O S

Y

O

N

NO CH3

YZH

34.9

146.0

p-Cl

33.0

138.1

p-Br

33.0

138.1

p-CH3

33.4

139.7

p-OCH3

33.7

141.0

m-NO2

33.9

141.8

2,5-2-Cl2

33.7

141.0

29.1

121.8

Amino-N-nitroso-N-phenylamide, substituted O

Y

N

NR2

N O RZMe

YZH

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 7.2 (continued) N–N BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

2-Cl

23.1

96.7

4-Cl

29.2

122.2

3-Br

30.3

126.8

4-Br

29.4

123.0

4-I

28.9

120.9

2-Me

27.5

115.1

4-Me

28.7

120.1

4-MeO

28.3

118.4

4-MeCO

30.5

127.6

4-NO2

33.1

138.5

YZ4-Me

26.6

111.3

RZC6H5CH2 YZ4-Me

25.4

106.3

RZi-Pr

Methods (reference in parentheses)

References

Nitrosophenyl(phenylsolfonyl)-amine, substituted

O

Y

N

O S

Ph

N O YZH

13.2

55.2

Cl

13.1

54.8

Me

11.4

47.7

MeO

12.4

51.9

MeCO

14.5

60.7

NO2

18.0

75.3

35.0 36.2 36.2 34.5 40.4

146.4 151.5 151.5 144.3 169.0

AOP

1998CHE/XIA

AOP

1998CHE/XIA

Diethyl(nitrosophenylamino)phosphino-1-one, substituted

O

Y N

OE t P

OE t

N O XZH Cl Br Me NO2

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BDEs of N–X Bonds

401

Nitrosoindole

N

28.7

120.1

AOP

2000ZHU/HE

29.7

124.3

AOP

2000ZHU/HE

27.4

114.6

AOP

2000ZHU/HE

28.3

118.4

AOP

2000ZHU/HE

13.6

56.9

AOP

2000ZHU/HE

19.2

80.3

AOP

2000ZHU/HE

22.9

95.8

AOP

2000ZHU/HE

NO Nitrosoindole, substituted

N NO 9-Nitrosocarbazole

N NO 3,6-Dibromo-9-nitrosocarbazole Br Br

N NO 10-Nitrosophenoxazine

O N NO

5-Nitroso-benzo(b,f)azepine

N NO

5-Nitroso-10H, 11Hdibenzo(b,f)azepine

N NO

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 7.2 (continued) N–N BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Nitrosodiphenylamine, substituted

Y1

Y2 N NO

Y1ZH m-Cl

Y2ZH H

22.6 24.1

94.6 100.8

AOP

2000ZHU/HE

m-Me

H

22.3

93.3

p-Me

H

21.4

89.5

p-NO2

H

24.3

101.7

p-MeO

H

21.4

89.5

p-MeO

p-MeO

21.0

87.9

Hydrogen azide HNaN2

15.0

62.8

Derived from DfH0 in ref.

1994FRE/KAB

Methyl azide CH3NaN2

41.7

174.4

Pyrolysis

2001ORL

Ethyl azide C2H5NaN2

38.0

159.0

Pyrolysis

2001ORL

Phenyl azide C6H5NaN2

36.8

153.9

Pyrolysis

1986STE/KRU

Benzyl azide C6H5CH2NaN2

38.2

159.7

Pyrolysis

1986STE/KRU

cyclo-Hexyl azide c-C6H11NaN2

38.2

159.7

Pyrolysis

1986STE/KRU

4-Aza-4-diazobut-4-en-2-one

37.8

158.1

Pyrolysis

1986STE/KRU

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BDEs of N–X Bonds

CH3C(O)CH2NaN2 1-Aza-1-diazopent-1-en-3-one C2H5C(O)CH2NaN2

403

38.0

159.0

Pyrolysis

1986STE/KRU

38.6

161.5

Pyrolysis

1986STE/KRU

R, R 0 ZCH3

16.5G1.9

69.1G7.8

Derived

2005ACR/PIL

tBu

18.7G1.8

78.3G7.5

p-NO2-benzyl azide 4-NO2C6H4CH2NaN2

Azo-N,N-dioxides R(O)N

N(O)R'

Azobenzene-N,N-dioxides, substituted

(O)N

N(O)

Y Y, Y 0 ZH

Y' (1) 21.8G2.0

91.2G8.5

(1) Derived

(1) 1993ACR/TUC

2-NO2

(2) 18.0G1.3

75.3G5.4

(2) Calorimetry

(2) 2005ACR/PIL

(3) NMR

(3) 1970OKA/INA

(4) Derived

(4) 1994ACR/TUC

2,4-Me2

(2) 17.7G2.9

74.2G12.2

2,4,6-Me3

(2) 17.3G2.9

72.3G12.2

2,4-Et2

(2) 19.3G3.1

80.7G13.1

2,3,5,6-Me4

(3) 14.6G1.2

61.1G5.0

2,3,4,5,6-Me5

(3) 12.0G1.2

50.2G5.0

4-N(Me)2

(4) 12.2

51

7.3

N–C bonds

Table 7.3 N–C BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CN radical CbN

(1) 175.9G4.3 (2) 179.3G0.7

736.2G18.0 750.0G2.9

(1) Spectroscopy (2) Derived from DfH0 in ref.

(1) 2003RED/AHA (2) This volume

Hydrogen cyanide

223.4G0.8

934.9G3.3

Derived from DfH0 in ref.

1996NIST

HCbN

(continued)

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404

Comprehensive Handbook of Chemical Bond Energies

Table 7.3 (continued) N–C BDEs

The broken bonds (boldfaceZdissociated group) Halogened cyanide XCbN XZF

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

165.4G3

kJ/mol

691.9G112.6

Methods (reference in parentheses)

References

Derived from DfH0 in ref.

1996NIST

Cl

185.9G4

777.8G16.7

Br

191G15

799G63

I

195G9

816G38

CH2N radicals CH2aN

144G6

602G25

PES

1991COW/TRA

CNN radicals C–N2

29.5G0.8

123.4G3.3

Derived from DfH0 in ref.

2000BIS/HOO

Diazomethylene CH2aN2

!41.7

!174.5

UV Photolysis

1971LAU/OKA

Isocyanic acid HNaCO

(1) %122.1G0.3 %510.9G1.3 (singlettriplet) (2) 86.6G1.2 362.3G5.0

(1) Photolysis

1996BRO/BER

Cyanogen azide N3–CN

(1) 96.9G2.3 (2) 109.5G5

405.2G9.6 458.1G20.9

(1) PD (2) Derived from DfH0 in ref.

(1) 1969OKA/MEL (2) 1996NIST

1-Aza-1-diazoethane N3–CH3

(1) 71.7 (2) 80.1G5

300.0 335.1G20.5

(1) Derived (2) Derived from DfH0 in ref.

(1) 1993PEP/MAT (2) 1988LIA/BAR

Azacyclopentyldiazomethen cyclo-C5H9–N3

(1) 76.1G6.9 (2) 76.2G3.3

318.4G28.9 318.8G13.8

(1) Derived (2) Calorimetry

(1) 1969OKA/MEL (2) 1993PEP/MAT

(2) Derived from DfH0 in ref.

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

405

Azacyclohexyldiazomethen cyclo-C6H11–N3

(1) 80.7G6.9 (2) 81.1G3.7

337.7G28.9 339.3G15.5

(1) Derived (2) Calorimetry

(1) 1969OKA/MEL (2) 1993PEP/MAT

Azadiazophenylmethane N3–C6H5

(1) 85.3G4.6 (2) 89.8G5

357G19 375.7G20.9

(1) 1969OKA/MEL (2) 1988LIA/BAR

(3) 89.0G4.4

372.4G18.4

(1) Derived (2) Derived from DfH0 in ref. (3) Derived

1-Aza-1-diazo-2-phenylethane 50.5G3.4 N3–CH2C6H5

211.3G14.2

Calorimetry

1993PEP/MAT

1-Aza-1-diazo-2,2,2triphenylethane N3–C(C6H5)3

46.6

195.0

Review

1974PEP/ERL

3-Aza-3-diazoprop-3-en-1-ol N3–CH2CH2OH

56.2G3.9

235.1G16.3

Calorimetry

1993PEP/MAT

Ethyl-3-aza-3-diazopro-3enoate N3–CH2C(O)OC2H5

66.8G3.9

279.5G16.3

Calorimetry

1993PEP/MAT

1-Aza-1-diazo-2,2,2trinitroethane N3–C(NO2)3

70.6G3.7

295.4G15.5

Calorimetry

1993PEP/MAT

1-Aza-1-diazo-2,2-dinitroprop- 66.4G3.7 1-ene N3–C(NO2)2Me

277.8G15.5

Calorimetry

1993PEP/MAT

Methyl isocyanide CH3–NC

(1) 101.5G2.2 (2) 98.7G0.8

424.7G9.2 413.0G3.3

Derived from DfH0 in ref.

(1) 1986PED/NAY (2) 2004KOI/BAE

Ethyl iso-cyanide C2H5–NC

(1) 100.1G1.7 (2) 98.8G2.0

418.8G7.1 413.4G8.4

Derived from DfH0 in ref.

(1) 1986PED/NAY (2) 2004KOI/BAE

Iso-propyl isocyanide

101.1G2.0

423.0G8.4

Derived from DfH0 in ref.

2004KOI/BAE

iso-C3H7–NC

(3) 1993PEP/MAT

(continued)

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406

Comprehensive Handbook of Chemical Bond Energies

Table 7.3 (continued) N–C BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated group)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Tert-butyl isocyanide tert-C4H9–NC

95.5G1.3

399.6G5.4

Derived from DfH0 in ref.

2004KOI/BAE

Nitrosyl cyanide NC–NO

(1) 28.8G2.5 (2) 48.8

120.5G10.5 204.4

(1) EI (2) Photofrag.

(1) 1975GOW/JON (2) 1987KHU/KNE

Nitrosomethane CH3–NO

(1) 40G0.8 (2) 41.1

167.4G3.3 172.0

(1) Pyrolysis (2) Spectroscopy

(1) 1973BAT/MIL (2) 1990MCC/PFA

Nitroso-trifluoromethane CF3–NO

(1) (2) (3) (4)

129.7G12.6 179.1G8.4 165.7G1.0 167

(1) EI (2) Pyrolysis (3) Photolysis (3) Spectroscopy

(1) 1973CAR/GOW (2) 1979GLA/MAI (3) 1983BOW/JON (3) 1990MCC/PFA

Nitroso-trichloromethane CCl3–NO

(1) 32G3 (2) 29.9

133.9G12.6 125

(1) EI (2) Photolysis

(1) 1973CAR/GOW (2) 1995LEY/MAS

Nitrosoethane C2H5–NO

41.0

171.5

Derived from DfH0 in ref.

1994NIST

3-Nitroso-1-propene CH2CHCH2–NO

26.3

110

FP

1995BOY/NOZ

2-Nitroso-propane iso-C3H7–NO

36.5G3

152.7G12.6

EI

1972CAR/GOW

2-Chloro-2-nitrosopropane Cl(CH3)2C–NO

36.9G0.6

154.3G2.4

Photofragment

1995TOM/WAL

Nitroso-tert-butane tert-C4H9–NO

(1) 29G3 (2) 39.5G1.5 (3) 39.9

121.3G12.6 165.3G6.3 167

(1) EI (2) VLPP (3) Laser excit.

(1) 1973CAR/GOW (2) 1974CHO/MEN (3) 1986NOB/QUI

31G3 42.8G2 39.6G0.2 39.9

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

407

2,2-Dimethyl-1-nitrosopropane 36 tert-BuCH2–NO

150.6

EI

1972CAR/GOW

Nitrosobenzene C6H5–NO

(1) 51.5G1 (2) 52.4G1.4

215.5 219.2G5.9

(1) 1975CHO/GOL (2) 1996NIST

(3) 54.2G0.5

226.8G2.1

(1) VLPP (2) Derived from DfH0 in ref. (3) Pyrolysis

Nitroso-pentafluorobenzene C6F5–NO

(1) 62G5 (2) 50.5G1

259.4G20.9 211.3G4.2

(1) EI (2) VLPP

(1) 1973CAR/GOW (2) 1975CHO/GOL

Nitrosotoluene C6H5CH2–NO

29.4

123

FP

1995BOY/NOZ

Nitromethyl radical C%H2–NO2

71.2G3

298G13

Derived

1993CYR/LEA

Nitromethane CH3–NO2

(1) 60.8 (2) 63.7 (3) 62.3G0.5

254.4 266.5 260.7G2.1

(1) 1981BAT/ROB (2) 1989CHE/ALB (3) 1996NIST

(4) 62.3G2.3 (5) 60G2

260.7G9.6 251.0G8.4

(1) Review (2) ECD (3) Derived from DfH0 in ref. (4) ECD (5) Evaluated

Nitroethylene C2H3–NO2

71.5

299.2

Derived from DfH0 in ref.

1999BUR

Nitroethane C2H5–NO2

(1) 58.6 (2) 60.8

245.2 254.4

(1) Review (2) Derived from DfH0 in ref.

(1) 1981BAT/ROB (2) 1986PED/NAY

1,1-Dichloro-1-nitro-propane CH3CCl2–NO2

58.3

244.0

Derived from DfH0 in ref.

1996NIST

(E)-nitro-propylene-2 (CH3)CHaCH–NO2

69.3

290.0

Derived from DfH0 in ref.

1999BUR

(3) 1997PAR/DYA

(4) 2002CHE/CHE (5) 2003NGU/LE

(continued)

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

408

Comprehensive Handbook of Chemical Bond Energies

Table 7.3 (continued) N–C BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1-Nitropropane nC3H7–NO2

61.3

256.5

Derived from DfH0 in ref.

1986PED/NAY

2-Nitropropane iso-C3H7–NO2

(1) 59.0 (2) 62.1

246.9 259.8

(1) Review (2) Derived from DfH0 in ref.

(1) 1981BAT/ROB (2) 1986PED/NAY

1-Nitrobutane nC4H9–NO2

(1) 60.9 (2) 61.2

254.8 256.0

Derived from DfH0 in ref.

(1) 1986PED/NAY (2) 2002KOS/MIR

2-Nitrobutane sec-C4H9–NO2

62.9

263.2

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-2-nitropropane tert-C4H9–NO2

(1) 58.5 (2) 61.8

244.8 258.6

(1) 1981BAT/ROB (2) 1986PED/NAY

(3) 58.8

(3) 246.0

(1) Review (2) Derived from DfH0 in ref. (3) Derived

(3) 2001MAT/LEB

Nitropentane nC5H11–NO2

(1) 60.4G1.5 (2) 60.2G1.5

252.7G6.3 251.9G6.3

Derived from DfH0 in ref.

(1) 1997VER (2) 1999BUR

Nitrohexane nC6H13–NO2

60.2

251.9

Derived from DfH0 in ref.

1999BUR

Nitro-cyclo-propane cyclo-C3H5–NO2

70.6

295.4

Derived from DfH0 in ref.

1999BUR

Nitro-cyclo-hexane cyclo-C6H11–NO2

64.0G1.5

267.8G6.3

Derived from DfH0 in ref.

1997VER

Nitrobenzene C6H5–NO2

(1) 71.3G1 (2) 71.4G2

298.3G4.2 298.7G8.4

(1) Review (2) VLPP

(1) 1981BAT/ROB (2) 1985GON/LAR

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

409

(3) 70.7G1

295.8G4.2

(3) Derived from DfH0 in ref.

(3) 1986PED/NAY

(1) 70.5

295.0

(1) Pyrolysis

(1) 1975MAT/NAS

(1) 72.2

302.0

(1) 66.5 (2) 73.2G2.4

278.2 306.3G10.0

(2) VLPP

(2) 1985GON/LAR

(1) 67.0

280.3

(2) 70.2G2.5

293.7G10.5

(2) 71.4G2.3

298.7G9.6

(1) 66.0

276.1

(2) 70.6G2

295.4G8.4

(1) 50.3G1.5

210.3G6.3

(1) 1986PED/NAY

(2) 47.0G2.3

196.6

(1) Derived from DfH0 in ref. (2) ECD

1-Nitronaphthalene 1-naphtyl–NO2

77.3G1.6

323.4G6.7

Derived from DfH0 in ref.

1986PED/NAY

Dinitromethane (NO2)CH2–NO2

(1) 48.8G2.5 (2) 49.5

204.2G10.5 207.1

(1) 1981BAT/ROB (2) 1986PED/NAY

(3) 55.1 (4) 52.2

230.5 218.4

(1) Review (2) Derived from DfH0 in ref. (3) Derived (4) Derived

46.5

194.4

Derived

1994NAZ/MAN

Nitrobenzene, substituted

Y

NO2

YZ3-NH2 DfH0(3-NH2-C6H4)Z76.5 (320.1) 4-NH2 DfH0(4-NH2-C6H4)Z78.3 (327.8) 3-NO2 DfH0(3-NO2-C6H4)Z81.4G2.4 (340.6G10.0) 4-NO2 DfH0(4-NO2-C6H4)Z72.3 (302.7) 2-Me DfH0(2-Me-C6H4)Z75.3G2.5 (315.1G10.5) 4-Me DfH0(3-NO2-C6H4)Z70.9G2.3 (296.6G9.6) 3,5-(NO2)2 DfH0(3,5-(NO2)2-C6H3)Z73.0 (305.4) 2-Me-4-NO2 DfH0(2-Me-4-NO2-C6H3)Z 70.6G2 (295.4G8.4)

Phenylnitromethane C6H5CH2–NO2

Dinitrodifluoromethane (NO2)CF2–NO2

(2) 1999CHE/WEL

(3) 1994NAZ/MAN (4) 2000MIR/VOR

(continued)

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Table 7.3 (continued) N–C BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1,1-Dinitroethane (CH3)CH(NO2)–NO2

(1) 46.3 (2) 50.5

193.6 211.3

Derived

(1) 1994NAZ.MAN (2) 2000MIR/VOR(b)

1,1-Dinitropropane (C2H5)CH(NO2)–NO2

(1) 47.2 (2) 49.9

197.3 208.8

Derived

(1) 1994NAZ.MAN (2) 2000MIR/VOR(b)

2,2-Dinitropropane (CH3)2C(NO2)–NO2

(1) 47.6 (2) 49.9

199.0 208.8

Derived

(1) 1994NAZ.MAN (2) 2000MIR/VOR(b)

1,1-Dinitrobutane (C3H7)CH(NO2)–NO2

50.5

211.3

Derived

2000MIR/VOR(b)

1,1-Dinitropentane (C4H9)CH(NO2)–NO2

49.3

206.1

Derived

2000MIR/VOR(b)

Trinitromethane (NO2)2CH–NO2

(1) 43.7G2.5 (2) 41.6 (3) 45.1

182.8G10.5 173.9 188.7

(1) Review (2) Derived (3) Derived

(1) 1981BAT/ROB (2) 1994NAZ/MAN (2) 2000MIR/VOR(a)

Trinitrofluoromethane (NO2)2CF–NO2

41.7

174.3

Derived

1994NAZ/MAN

Trinitrochloromethane (NO2)2CCl–NO2

36.6

153.3

Derived

1994NAZ/MAN

Trinitrobromomethane (NO2)2CBr–NO2

35.4

148.3

Derived

1994NAZ/MAN

1,1,1-Trinitroethane (CH3)(NO2)2C–NO2

(1) 42.4 (2) 42.7

177.2 178.7

Derived

(1) 1994NAZ.MAN (2) 2000MIR/VOR(b)

1,1,1-Trinitropropane (C2H5)(NO2)2C–NO2

(1) 41.5 (2) 41.9

173.5 175.3

Derived

(1) 1994NAZ.MAN (2) 2000MIR/VOR(b)

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BDEs of N–X Bonds

411

1,1,1-Trinitrobutane (C3H7)(NO2)2C–NO2

41.5

173.6

Derived

2000MIR/VOR(b)

1,1,1-Trinitropentane (C4H9)(NO2)2C–NO2

40.7

170.3

Derived

2000MIR/VOR(b)

Tetra-nitromethane (NO3)3C–NO2

(1) 40.5G1 (2) 33.6 (3) 42.1

169.5G4.2 140.7 176.1

(1) Review (2) Derived (3) Derived

(1) 1981BAT/ROB (2) 1994NAZ/MAN (3) 2000MIR/VOR(a)

1,1,1,2,2-Pentanitrofluoroethane 35.9 (NO2)2FC(NO2)2C–NO2

150.0

Derived

1994NAZ/MAN

1,1,1,2,2,2-Hexanitroethane (NO2)3C(NO2)2C–NO2

(1) 35.2 (2) 35.8

147.1 149.8

Derived

(1) 1994NAZ.MAN (2) 2000MIR/VOR(b)

2-Nitrofuran O NO

70.4

294.6

Pyrolysis

1987PRO/NAZ

Difluoro(trifluoromethyl)amine CF3–NF2

67.1

280.7

Derived from DfH0 in ref.

1977PED/RYL

Tert-butyldifluoroamine tert-C4H9–NF2

67.6G2.5

282.8G10.5

Derived from DfH0 in ref.

1996NIST

N,N-difluorobenzylamine C6H5CH2–NF2

56.7G3.5

237.2G14.6

Derived from DfH0 in ref.

1996NIST

2,2-Bis(difluoroamino) propane (1) w47 (CH3)2(NF2)C–NF2 (2) 47.8

w196.6 200.0

(1) Pyrolysis (2) Pyrolysis

(1) 1993FOK/GRE (2) 2002PAR/CHA

Methylamine CH3–NH2

(1) 85.1G0.5

356.1G2.1

(1) 1986PED/NAY

(2) 86.0 (3) 84.1

359.8 351.8

(1) Derived from DfH0 in ref. (2) Derived (3) Derived

2

(2) 2001KOS/MIR (3) 2003MIR/KON

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 7.3 (continued) N–C BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Acetaldimine C2H3–NH2

102.1

427.2

Derived from DfH0 in ref.

1988LIA/LIE

Ethylamine C2H5–NH2

(1) 84.2G1.5

352.3G6.3

(1) 1986PED/NAY

(2) 82.1

343.3

(1) Derived from DfH0 in ref. (2) Derived

Cyclo-propylamine cyclo-C3H5–NH2

92.8G0.6

388.3G2.5

Derived from DfH0 in ref.

1986PED/NAY

1-Propylamine nC3H7–NH2

85.1G0.7

356.1G2.9

Derived from DfH0 in ref.

1986PED/NAY

2-Propylamine iso-C3H7–NH2

85.5G0.9

357.7G3.8

Derived from DfH0 in ref.

1986PED/NAY

Cyclo-butylamine cyclo-C4H7–NH2

86.0G1.2

359.8G5.0

Derived from DfH0 in ref.

1986PED/NAY

1-Butylamine nC4H9–NH2

85.1G0.7

356.1G2.9

Derived from DfH0 in ref.

1986PED/NAY

2-Butylamine sec-C4H9–NH2

85.8G0.7

359.0G2.9

Derived from DfH0 in ref.

1986PED/NAY

Iso-butylamine iso-C4H9–NH2

84.8G1.2

254.8G5.0

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-2-propylamine tert-C4H9–NH2

85.0G1.5

355.6G6.3

Derived from DfH0 in ref.

1986PED/NAY

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

(2) 2003MIR/KON

BDEs of N–X Bonds

413

Cyclo-pentyamine cyclo-C5H9–NH2

82.9G1.2

346.9G5.0

Derived from DfH0 in ref.

1986PED/NAY

2-Pyridylamine pyridin-2-yl–NH2

103.0

431.0

Derived from DfH0 in ref.

1988LIA/BAR

3-Pyridylamine pyridin-3-yl–NH2

104.0

435.1

Derived from DfH0 in ref.

1988LIA/BAR

4-Pyridylamine pyridin-4-yl–NH2

107.0

447.7

Derived from DfH0 in ref.

1988LIA/BAR

Aniline or benzenamine C6H5–NH2

102.6G1.0

429.3G4.2

Derived from DfH0 in ref.

1986PED/NAY

Cyclo-hexylamine cyclo-C6H11–NH2

87.6G1.5

366.5G6.3

Derived from DfH0 in ref.

1986PED/NAY

Benzylamine C6H5CH2–NH2

(1) 71.1G1 (2) 73.3G1.5

297.5G4.2 306.7G6.3

(1) 1972GOL/SOL (2) 1986PED/NAY

(3) 72.9G1, 0K

305G4

(1) VLPP (2) Derived from DfH0 in ref. (3) Shock tube

a-Methylbenzylamine C6H5CH(CH)3–NH2

73.5G2.3

307.5G9.6

Derived from DfH0 in ref.

1999VER

a,a-dimethylbenzylamine C6H5C(CH3)2–NH2

72.8G2.3

304.6G9.6

Derived from DfH0 in ref.

1999VER

1-Naphthylamine 1-naphtyl–NH2

102.8G2

430.1G8.4

Derived from DfH0 in ref.

1986PED/NAY

2-Naphthylamine 2-naphtyl–NH2

108.3G2

453.1G8.4

Derived from DfH0 in ref.

1986PED/NAY

Formamide HC(O)–NH2

(1) 99.0 (2) 100.8G2

414.2 421.7G8.4

Derived from DfH0 in ref.

(1) 1996NIST (2) 2002CRC

(3) 2002SON/GOL

(continued)

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

414

Comprehensive Handbook of Chemical Bond Energies

Table 7.3 (continued) N–C BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Acetamide CH3C(O)–NH2

99.1G2

414.6G8.4

Derived from DfH0 in ref.

2002CRC

Propanamide C2H5C(O)–NH2

98.7

413.0

Derived from DfH0 in ref.

1996NIST

Benzamide C6H5C(O)–NH2

96.4

403.3

Derived from DfH0 in ref.

1996NIST

Ethane-1,2-diamine H2NCH2CH2–NH2

78.0

326.2

Derived

2003MIR/KON

Methyl hydrazine CH3–NHNH2

70.7G2.5

295.8G10.5

Derived from DfH0 in ref.

1986PED/NAY

Phenyl hydrazine C6H5–NHNH2

88.6G2.5

370.7G10.5

Derived from DfH0 in ref.

1986PED/NAY

N,N,N 0 N 0 -methylmethanediamine (CH3)2N–CH2N(CH3)2

55.6G3

232.6G12.6

Derived from DfH0 in ref.

1986PED/NAY

Dimethylamine CH3–NHCH3

(1) 82.2G2.5 (2) 81.9

343.9G10.5 342.7

Derived

(1) 1982MCM/GOL (2) 2001KOS/MIR

Ethyl methylamine C2H5–NHCH3

79.8G1

333.9G4.2

Derived

1982MCM/GOL

Phenyl methylamine C6H5–NHCH3

100.6G2.5

420.9G10.5

Derived

1982MCM/GOL

Benzyl methylamine C6H5CH2–NHCH3

68.7G2

287.4G8.4

VLPP

1972GOL/SOL

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

415

N-methyl acetamide CH3C(O)–NHCH3

100.9

422.2

Derived from DfH0 in ref.

1996NIST

Trimethylamine CH3–N(CH3)2

(1) 75.5G2.5 (2) 78.6G2

315.9G10.5 328.9

(1) 1982MCM/GOL (2) 1996NIST

(3) 79.3

331.8

(1) Derived (2) Derived from DfH0 in ref. (3) Derived

Ethyl dimethylamine C2H5–N(CH3)2

72.3G2

302.5G8.4

Derived

1982MCM/GOL

1,1-Dimethylhydrazine CH3–N(CH3)NH2

90

377

Pyrolysis

1964EBE

Phenyl dimethylamine C6H5–N(CH3)2

93.2G2.5

389.9G10.5

Derived

1982MCM/GOL

Benzyl dimethylamine C6H5CH2–N(CH3)2

(1) 62.1G2.5 (2) 68.1

259.8G10.5 284.9

(1) VLPP (2) Derived from DfH0 in ref.

(1) 1972GOL/SOL (2) 1999VER

1-Methylpyrrile CH3–pyrrol-1-yl

81.3G2

340.2G8.4

Derived from DfH0 in ref.

2002CRC

N-methylaniline CH3–NHC6H5

(1) 71.4G2 (2) 68.9

298.7G8.4 288.3

(1) VLPP (2) Pyrolysis

(1) 1978COL/BEN (2) 1990BEC/DOG

N-ethylaniline C2H5–NHC6H5

(1) 73.3G2 (2) 70.9G2

306.7G8.4 296.6G8.4

Derived from DfH0 in ref.

(1) 1986PED/NAY (2) 1997VER(b)

Diphenylamide C6H5–NHC6H5

87.4

365.7

Derived from DfH0 in ref.

1969BEN/CRU

N-benzylaniline PhCH2–NHC6H5

58.9

246.4

Derived from DfH0 in ref.

1997VER(b)

(3) 2001KOS/MIR

(continued)

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

416

Comprehensive Handbook of Chemical Bond Energies

Table 7.3 (continued) N–C BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

N,N 0 -methylaniline CH3–N(CH3)C6H5

70.8

296.2

VLPP

1978COL/BEN

Dimethyl phenylamine C6H5(CH3)N–CH3

70.8G2

296.2G8.4

VLPP

1978COL/BEN

Dimethyl benzylamine (CH3)2N–CH2Ph

62.1G2

259.8G8.4

VLPP

1972GOL/SOL

Azomethane CH3–N2CH3

52.5

219.7

Pyrolysis

1970BEN/ONE

Azohexafluoroethane CF3–N2CF3

55.2

231.0

Pyrolysis

1970BEN/ONE

Azoethane C2H5–N2C2H5

50

209.2

Pyrolysis

1970BEN/ONE

Azoisopropane iso-C3H7–N2-iso-C3H7

47.3

197.9

Pyrolysis

1970BEN/ONE

Azobutane nC4H9–N2-nC4H9

50

209.2

Pyrolysis

1970BEN/ONE

Azoisobutane iso-C4H9–N2-iso-C4H9

49

205.0

Pyrolysis

1970BEN/ONE

Azo-2-butane sec-C4H9–N2-sec-C4H9

46.7

195.4

Pyrolysis

1970BEN/ONE

Azotertbutane tert-C4H9–N2-tert-C4H9

43.5

182.0

Pyrolysis

1970BEN/ONE

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

417

Azobenzene C6H5N2–C6H5

60.6

253.8

PI

1998SHE/WU

p-Aminoazobenzene p-NH2–C6H4N2-C6H5

63.0G2.3

263.4G9.6

PI

1999WU/SHE

p-Hydroxyazobenzene p-OHC6H4–N2C6H5

82.3G1.2

344.4G4.8

PI

2001CHE/ZHA

p-Hydroxyazobenzene p-OH-C6H4N2–C6H5

48.0G1.2

200.7G4.8

PI

2001CHE/ZHA

Azotoluene C6H5CH2–N2CH2C6H5

37.6

157.3

Pyrolysis

1970BEN/ONE

Nitro[(nitroamino)methyl]amine 45.8 (NHNO2)–CH2(NHNO2)

191.6

Derived

2003MIR/KON

Nitro[2-(nitroamino)ethyl]amine 49.5 (NHNO2)–CH2CH2(NHNO2)

207.3

Derived

2003MIR/KON

Nitro[5-(nitroamino)pentyl]amine 47.5 (NHNO2)–CH2(CH2)5 (NHNO2)

198.7

Derived

2003MIR/KON

N,N-dimethylformamide HC(O)–N(CH3)2

(1) 89.7G3.2 (2) 93.7G2

375.3G13.4 392.0G8.4

(1) Derived (2) Derived from DfH0 in ref.

(1) 1999FOR/BUT (2) 2002CRC

N-methyl-acetamide CH3C(O)–NH(CH3)

100.9

422.2

Derived from DfH0 in ref.

1996NIST

N,N-dimethylacetamide CH3C(O)–N(CH3)2

91.4

382.4

Derived from DfH0 in ref.

1986PED/NAY

(continued)

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

418

Comprehensive Handbook of Chemical Bond Energies

Table 7.3 (continued) N–C BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

90.0

376.7

Derived from DfH0 in ref.

1996NIST

1-(dimethylamino)-2-propanone 72.7 CH3C(O)CH2–N(CH3)2

304.2

Derived from DfH0 in ref.

1996NIST

N,N-dimethylformamide CH3–N(CH3)C(O)H

w80

w335

Derived

1999FOR/BUT

Methylnitroamine CH3–NHNO2

(1) 71.0 (2) 68.8

297.1 287.9

Derived

(1) 2001KOS/MIR (2) 2003MIR/KON

Dimethylnitroamine CH3–N(CH3)NO2

69.8

292.0

Derived

2001KOS/MIR

Methyl((methylnitroamino)methyl)nitroamine CH3N(NO2)CH2–N(NO2)CH3

70.1

293.3

Derived

2001KOS/MIR

Nitrozoamines (NO2)3CCH2–N(NO2)H2C(NO2)3 53.5

223.8

Derived

2001MIR/KOS

Derived

1998BEC/WAL

N,N-dimethyl-propanamide C2H5C(O)–N(CH3)2

(NO2)2CHCH2–N(NO2)CH2CH(NO2)2

59.0

246.9

(NO2)3CCH2–N(NO2)CH2CH2C(NO2)3

64.0

267.8

(NO2)3CCH2–N(NO2)CH2N(NO2)CH2C(NO2)3

52.6

220.1

(NO2)2CHCH2–N(NO2)57.9 (CH2)2N(NO2)CH2CH(NO2)2

242.3

(NO2)3CCH2–N(NO)CH2C(NO2)3

53.3

223.0

(NO2)3CCH2–N(NO)(CH2)2N(NO)CH2C(NO2)3

49.5

207.1

Bis(1,1-dimethyl-silaethyl)methylamine CH3–N(SiMe3)2

87

364

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

BDEs of N–X Bonds

419

Amonomethanenitrile H2N–CN

118.8G3

497.1G12.6

Derived from DfH0 in ref.

2001BIS/HOO

N-(aminocarbonyl)acetamide HC(O)–NHC(O)NH2

115.6G2

483.7G8.4

Derived from DfH0 in ref.

2002CRC

N-methylglycine or sarcosine HO(O)CCH2–NHCH3

72.3G2

302.5G8.4

Derived from DfH0 in ref.

2002CRC

a-Aminino-benzeneacetic acid 63.1G2 HO(O)CCH2–NHC6H5

264.0G8.4

Derived from DfH0 in ref.

1996NIST

Methanisothiocyanate CH3–NCS

315.9

Derived from DfH0 in ref.

1996NIST

Derived

1973LAR/JOH

Derived from DfH0 in ref.

1996NIST

75.5

F2SN–CN

64G5

268G21

F2SN–CF3

39G7

163G19

CH3–NHC%H2

13.7G3

57.3G12.6

CH3–N(CH3)C%H2

10.7G3

44.8G12.6

C6H5–N(CH3)C%H2

26.3G3

110.0G12.6

CF3–N

39G3

163G13

Derived

1973LAR/JOH

C6H5CH2–N2

w1.1

w4.8

Spectroscopy

1993DIS/BER

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

420

7.4

Comprehensive Handbook of Chemical Bond Energies

N–S bonds

Table 7.4 N–S BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Thiazyl S–N

111.6G5.7

467G24

Review

2004LOD

Nitrothiol HS–NO

33.2

138.9

Derived from DfH0 in ref.

1984BLA/PAT

(Nitrothio)methyl acetate CH3C(O)OCH2S–NO

19.1

80

AOP

2000LU/ZHU

Methylnitrosothio CH3S–NO

25G1

104.6G4.2

Review

1978BEN

(Tert-butyl)nitrosothio tert-BuS–NO

27.5

115.1

AOP

2001LU/WIT

(Hexyl)nitrosothio CH3(CH2)5S–NO

28.9G0.3

120.9G1.3

Pyrolysis

2001BAR/MAN

(Cyclo-hexyl)nitrosothio cyclo-C6H11S–NO

31.6G0.8

132.2G3.3

Pyrolysis

2001BAR/MAN

(Benzyl)nitrosothio PhCH2S–NO

28.8

120.5

AOP

2001LU/WIT

(Triaryl)nitrosothio (Ar)3S–NO

29G1

121.3G4.2

Review

1978BEN

(2) 19.4G1.3

81.2G5.4

AOP

(2) 19.3G1.5

80.8G6.3

(Phenyl)nitrosothio, substituted

Y YZH 2-Cl

S

NO

7366—CHAPTER 7—3/2/2007—20:44—CRCPAG—15363—XML MODEL B – pp. 369–424

(1) 2000LU/ZHU (2) 2001LU/WIT

BDEs of N–X Bonds

421

3-Cl

(2) 20.9G1.4

87.4G5.9

4-Cl

(2) 19.2G1.4

80.3G5.9

2-Me

(1) 17.2G1.4

72G5.9

3-Me

(2) 19.9G1.2

83.3G5.0

4-Me

(2) 21.4G1.2

89.5G5.0

4-MeO

(2) 21.0G1.9

87.9G7.9

4-NO2

(2) 18.6G1.5

77.8G6.3

Thiazyl trifluoride NbSF3

(1) 93G3 (2) 100G2

389.1G12.6 418G8

(1) Calorimetry (2) Derived

(1) 1970OHA/HUB (2) 1973LAR/JOH

Thiazyl difluoride NbSF2

63G8

264G33

Derived

1973LAR/JOH

Thiazyl fluoride NbSF

(1) 71G5 (2) 126G3

297G21 527G13

(1) Calorimetry (2) Derived

(1) 1970OHA/HUB (2) 1973LAR/JOH

Phenylphenylthiodiazene PhNaN-SPh

29G1

121.3G4.2

Review

1978BEN

Thiocyanogen SCN–SCN

61.1

255.6

Derived from DfH0 in ref.

1998CHA

Fluorosulfuryldifluoramine FSO2–NF2

39

163

MS

1965PAU/LUS

Bis(fluorosulfuryl)fluoramine (FSO2)2–NF2

48

201

MS

1965PAU/LUS

Pentafluorosulfur difluororamine SF5–NF2

32

134

MS

1965PAU/LUS

F2S–NCN

42G3

176G13

Derived

1973LAR/JOH

F2S–NCF3

61G3

255G13

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422

7.5

Comprehensive Handbook of Chemical Bond Energies

N–halogen bonds

Table 7.5 N–Halogen BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Nitrosyl fluoride F–NO

56.23

235.26

Derived from DfH0 in ref.

2003NASA/JPL

Nitryl fluoride F–NO2

52.9

221.3

Derived from DfH0 in ref.

2003NASA/JPL

Nitrogen trifluoride F–NF2

(1) 60.7

254.0

(1) Derived from DfH0 in ref.

(1) 1998CHA

F–NF

(1) 58.8

246.0

F–N

(2) 70.1G8.1 (3) 82.0 (4) %83.3

293.3G33.8 343.1 %349

(2) Derived (3) Spectroscopy (4) IR CL

(2) 1970CLA/CLY (3) 1979HUB/HER (4) 1988DU/SET

Fluoroamine F–NH2

68.5

286.6

Derived from DfH0 in ref.

1994NIST

Difluoroamine F–NHF

70.4

294.6

Derived from DfH0 in ref.

1989GUR/VEY

Nitrogen monochloride Cl–N

79.8G2.3

333.9G9.6

Derived

1970CLA/CLY

Nitrosyl chloride Cl–NO

38.0G0.2

158.8G0.8

Derived from DfH0 in ref.

2003NASA/JPL

Nitryl chloride Cl–NO2

33.9G0.3

141.8G1.3

Derived from DfH0 in ref.

2003NASA/JPL

Nitrogen chlorofluoride Cl–NF2

w 32

w134

Kinetics

1967PET

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BDEs of N–X Bonds

423

Chloramide Cl–NH2

60.5

253.1

Derived from DfH0 in ref.

1994NIST

Chlorine azide Cl–N3

(1) 32.5G3.2 (2) 51.7G2.3

136.0G13.5 216.1G9.6

(1) Derived (2) Photolysis

(1) 1970CLA/CLY (2) 2003HAN/WOD

Isocyanato chloride Cl–NCO

46.6

195

Est. by exp.

2005GAO/MAC

Nitrogen monobromide Br–N

67.1G5

280.8G21

Devived

1970CLA/CLY

Nitrosyl bromide Br–NO

28.7G0.2

120.1G0.8

Derived from DfH0 in ref.

2003NASA/JPL

Nitryl bromide Br–NO2

19.6G1.7

82.0G7.1

Fluorescence

1991KRE/NIC

Nitrogen bromofluoride Br–NF2

!54.3

!227.2

Kinetics

1972CLY/CON

Nitrogen iodide I–N

38G4

159G17

Review

1974GUR/KAR

Nitrosyl iodide I–NO

(1) 18.6G0.1 (2) 18.1G1

77.8G0.4 75.6G4

(1) UV spectra (2) Derived from DfH0 in ref.

(1) 1981FOR/HIP (2) 2003NASA/JPL

Nitryl iodide I–NO2

(1) 18.3G1.0 (2) 19.0G1

76.6G0.4 79.6G4

(1) Spectroscopy (2) Derived from DfHH in ref.

(1) 1976VAN/TRO (2) 2003NASA/JPL

Electrochemical

N-halogenosuccinimide X O

N

O

XZ Cl

(1) 73G4

305.4G16.7

Br

(2) 66G2

276.1G8.4

(1) 1993LIN/JON (2) 1998LIN/MER

(continued)

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Table 7.5 (continued) N–Halogen BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1-Bromo-2,6-piperidione

Br O

N 61 2 5 3 4

O

65G2

272.0G8.4

Electrochemical

1998LIN/MER

Note: (1) The BDEs in the clusters and complexes of hydrocarbon and carbon ions are listed in Table 24.1; (2) The BDEs in the clusters and complexes of oxygen, nitrogen, and sulfur ions are listed in Table 25.1, Table 25.2, and Table 26.1, respectively; (3) The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27.

7.6

N–B, N–Al, N–Ga, and N–In bonds

The BDEs in the bonds are listed in Chapter 23. Note: 1. The data of N–O bonds see the O–N bonds on page 295 2. The BDEs in the clusters and complexes of C-, Si-, Ge-, Sn-, and Pb-ions are listed in Chapter 24. 3. The BDEs in the clusters and complexes of N-, P-As-, Sb-, and Bi–ions are listed in Chapter 25. 4. The BDEs in the clusters and complexes of O-, S-, Se-, Te-, and Po-ions are listed in Chapter 26. 5. The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27.

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chapter eight

BDEs of S–, Se–, Te–, Po–X bonds 8.1

S–H bonds

Table 8.1 S–H BDEs

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Hydrogen sulfide H–SH DfH0(R)Z34.2G0.2 (143.0G0.8)

(1) 91.1G1 (2) 91.2G0.7 (3) 91.2G0.7 (4) 91.2G0.1 (5) 91.10G0.01

381.2G4.2 381.6G2.9 381.6G2.9 381.4G0.5 381.18G0.05

(1) Iodination (2) Fluorescence (3) Recommended (4) Photolysis (5) Spectroscopy

(1) 1979HWA/BEN (2) 1992STI/NIC (3) 1994BER/ELL (4) 1996WIL/HOW (5) 2000SHI/HU

Mercapto radical H–S

(1) 83.4

349.1

(1) PIMS

(1) 1986GIB/GRE

(2) 84.4G0.7 (3) 84.66G0.29 (4) 84.6G1.0 (5) 84.50G0.07

353.1G2.9 354.21G1.20 353.9G4.3 353.57G0.30

(2) PD (3) Photofrag. (4) Derived (5) PD

(2) 1991CON/BAL (3) 1993MOR/LAM (4) 2000REM/ERV (5) 2005ZHO/YUA

Hydrogen sulfide-d2 D–SD

(1) 92.76G0.14 388.10G0.60 (2) R92.31G0.06 R386.24G0.26

(1) Photofrag. (2) PI

(1) 1993MOR/LAM (2) 2001COO/LAN

Mercapto radical-d D–S

(1) 83.9 (2) 83.80G0.29

351 350.62G1.20

(1) Spectroscopy (2) Photofrag.

(1) 1979HUB/HRER (2) 1993MOR/LAM

Mercapto fluoride H–SF

56.9

237.9

Derived from DfH0 in ref.

2005HOW/MAY

(continued)

425

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Comprehensive Handbook of Chemical Bond Energies

Table 8.1 (continued) S–H BDEs

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol) Methylthiol H–SCH3 DfH0(R)Z29.8G0.4 (124.7G1.7)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 88.1 (2) 86.4G2.2 (3) 87.4 (4) 87.4G0.5 (5) 87.0G0.4 (6) 88.3G2

368.6 361.5G9.2 365.7 365.7G2.1 364.0G1.7 369.4G8.4

(1) VLPP (2) PES (3) Fluorescence (4) Recommended (5) Photolysis (6) PEDt

(1) 1977COL/BEN(b) (2) 1987MOR/ELL (3) 1992NIC/KRE (4) 1994BER/ELL (5) 1999BIS/CHO (6) 1980JAN/REE

Ethene-1-thiol H–SCHCH2

84G2

351.5G8.4

Review

1978BEN

Ethylthiol H–SC2H5 DfH0(R)Z24.1 (101)

(1) 88.6G2

370.7G8.4

(1) PEDt

(1) 1980JAN/REE

(2) 87.3

365.3

(2) 1986PED/NAY

(3) 87.5

366.0

(2) Derived from DfH0 in ref. (3) Correlation

(1) 88.6G2

370.7G8.4

(1) PEDt

(1) 1980JAN/REE

(2) 87.4

365.7

(2) 1986PED/NAY

(3) 87.8

367.3

(2) Derived from DfH0 in ref. (3) Correlation

Iso-propylthiol H–S-iso-C3H7 DfH0(R)Z17.9G2 (74.9G8.4)

(1) 88.4G2

369.9G8.4

(1) PEDt

(1) 1980JAN/REE

(2) 87.7

366.9

(2) Correlation

(2) 2005DEN/TUM

n-Butylthiol H–S-n-C4H9

(1) 87.1G2.3 (2) 87.5

364.4G9.6 366.0

(1) Derived (2) Correlation

(1) 2004FAT/KAS (2) 2005DEN/TUM

tert-Butylthiol H–S-tert-C4H9 DfH0(R)Z10.5G2 (43.9G8.4)

(1) 88.6G2

370.7G8.4

(1) PEDt

(1) 1980JAN/REE

(2) 86.6G2.2

362.3G9.2

(2) GPA

(2) 2003REE/HAR

Octane-2-thiol H–SCH(CH3)(CH2)5CH3

88.3

369.3

Correlation

2005DEN/TUM

H–SCD3

Propylthiol H–SC3H7 DfH0(R)Z19.1 (80)

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(3) 2005DEN/TUM

(3) 2005DEN/TUM

BDEs of S–, Se–, Te–, Po–X Bonds

427

Decanethiol H–S-n-C10H21

88.1

368.6

Correlation

2005DEN/TUM

Dodecanethiol H–S-n-C12H25

87.9

367.7

Correlation

2005DEN/TUM

2,4,4,6,6-Pentamethyl pentane-2-thiol H–SCMe2CH2CMe2CH2tBu

87.9

367.9

Correlation

2005DEN/TUM

Alkyl thiol H–SR

87.4

365.7

Review

1992NIC/KRE

87.1

364.4

Correlation

2005DEN/TUM

(1) 83.3G2 (2) 79.4 (3) 80 (4) 80.8 (5) 83.5G1.1

348.5G8.4 332.2 334.7 338.1 349.4G4.5

(1) VLPP (2) AOP (3) AOP (4) Correlation (5) TR-PAC

(1) 1982MCM/GOL (2) 1992VEN/AMA (3) 1996ARM/SUN (4) 2000DEN/DEN (5) 2002SAN/MUR

YZ2-Cl

(1) 80.0

334.7

(1) AOP

(1) 1994BOR/ZHA(b)

3-Cl

(1) 80.1 (4) 80.3

335.1 335.8

(2) AOP (3) AOP

(2) 1992VEN/AMA (3) 1997ZHU/ZHA

4-Cl

(1) 79.2 (4) 79.9 (5) 86.1G0.8

331.4 334.1 360.4G3.5

(4) Correlation (5) TR-PAC

(4) 2000DEN/DEN (5) 2002SAN/MUR

4-Br

(1) 79.3 (2) 80.2

331.8 335.6

4-NH2

(1) 69.8 (2) 70.0

292.0 292.9

2-Me

(1) 78.8

329.7

3-Me

(1) 78.9 (4) 80.8

330.1 338.1

Cyclo-hexanethiol

H S

H

Benzenethiol PhS–H DfH0(R)Z58.0G1.1 (242.7G4.6)

Benzenethiol, substituted

S

Y

H

(continued)

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Table 8.1 (continued) S–H BDEs

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

4-Me

(1) 78.3 (2) 77.8 (3) 78.4 (4) 80.0 (5) 84.8G1.0

327.6 325.5 328.0 334.8 354.9G4.1

4-MeO

(1) 76.9 (2) 76.2 (3) 78.6 (4) 78.7 (5) 83.3G1.0

321.7 318.8 328.9 329.3 348.5G4.0

3-CF3

(4) 80.8

338.1

4-CF3

(1) 80.9 (5) 86.0G0.9

338.5 359.9G3.9

2-MeCO2

(1) 78.7

329.3

4-NO2

(1) 81.4 (2) 81.6

340.6 341.4

4-OH

(2) 76.0

318.0

4-EtO

(4) 78.8

329.6

4-tert-Bu

(4) 80.7

337.7

2,4,6-Me3

(4) 80.4

336.6

Benzenethiol C6Cl5S–H

87.6

366.5

Derived from DfH0 in ref.

2000MUF/KHA

Phenylmethane-1-thiol PhCH2S–H DfH0(R)Z58.9 (246.4)

(1) 86.9

363.6

(1) AOP

(1) 1994BOR/ZHA(b)

(2) 87.8

367.4

(2) Correlation

(2) 1996DEN

Oxythio radical H–SO DfH0(R)Z1.2G0.3 (5.0G1.3)

(1) 41.3 (2) 58.5G2

172.8 244.8G8

(1) Kinetics (2) Derived from DfH0 in ref.

(1) 1978WHI/GAR (2) 2005DEN

Oxythio H–SOH DfH0(R)ZK1.6G0.5 (K6.7G2.1)

79G3.5

330.5G14.6

Ion flow tube

1993OHA/DEP

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BDEs of S–, Se–, Te–, Po–X Bonds

429

Thioacetic acid H–SCOCH3

88.6

370.7

Electrochemical

1999ZHA/LIN

Thiobenzoic acid H–SCOPh

87

364.0

Pulse radiolysis

1998ZHA/LIN

87.4

365.7

AOP

2000ZHA/LIN

CH3

87

364.0

Benzoylthiolate, substituted O

Y

S

C

H

YZH

CH3O

87

364.0

CF3

86

359.8

CN

86

359.8

%95

%397

Kinetics

1976HOR

2-Hydroxyethanedithioic acid 88.0 HOCH2C(S)S–H

368.2

Correlation

2005DEN/TUM

Phenylmethanedithioc acid PhC(S)S–H

87.9

367.9

Correlation

2005DEN/TUM

2-Amino-3-sulfanyl propanoic acid H–SCH2CH(NH2) C(O)OH

86.0

360.0

Correlation

2005DEN/TUM

2-Amino-4-methyl-3sulfanylpentanoic acid (CH3)2SHCH(NH2) C(O)OH

86.8

363.1

Correlation

2005DEN/TUM

86.1

360.3

Correlation

2005DEN/TUM

Methylsulfone H–SO2CH3

Amino-acid NH2 HO(O)C

S

NH O

O

NH

H

C(O)OH

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 8.1 (continued) S–H BDEs

The broken bonds (boldfaceZdissociated atom) DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Naphthalenethiol

1 4

S

H

2 3

H–S at site 1

(1) 78.5

328.4

(1) Correlation

(1) 2000DEN/DEN

2

(1) 78.1 (2) 77.9

326.8 325.9

(2) AOP

(2) 1994BOR/ZHA(b)

80.0

334.7

Correlation

2000DEN/DEN

Hydrogen disulfide radicals H–SS%

55.2G4

231.0G16.7

Derived from DfH0 in ref.

1993OHA/DEP

Hydrogen disulfide H–SSH DfH0(R)Z27.6G3.5 (115.5G14.6)

(1) 76G3.5 (2) 77.7

318.0G14.6 325.0

(1) Ion flow tube (2) Correlation

(1) 1993OHA/DEP (2) 2005DEN/TUM

Hydrogen methyl disulfide H–SSMe DfH0(R)Z16.4G2 (68.6G8.4)

(1) 79G3.5 (2) 70.5

330.5G14.6 295.0

(1) Ion flow tube (2) Correlation

(1) 1993OHA/DEP (2) 2005DEN/TUM

Hydrogen alkyl disulfide H–SSR

70G1.5

292.9G6.5

Review

1978BEN

Thio-a-tocopherol H

R5

S

R7

O CH3

CH 2

R

CH3

R = CH2CH2CHCH2

H

3

CH 3

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BDEs of S–, Se–, Te–, Po–X Bonds

431

Hydrogen trisulfide H–SSSH

70G1.5

292.9G6.5

Review

1978BEN

Hydrogen polysulfide H–S3CnH

70G1.5

292.9G6.5

Review

1978BEN

Hydrogen alkyl polysulfide H–S3CnR

70G1.5

292.9G6.5

Review

1978BEN

Thiocynic acid H–SCN

%93.3G1.1

%390.4G4.6

PIMS

1994RUS/BER(b)

H–SC%H2

44.1G2.5

184.5G10.5

Derived from DfH0 in ref.

1996NIST

8.2

S–S bonds

Table 8.2 S–S BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Disulfur S–S

101.65

425.30

Spectroscopy

1979HUB/HER

Disulfur cation SC–S (Also see Chapter 26)

(1) 123.8 (2) 124.9G0.1

518.1 522.4G0.5

(1) Derived (2) PI

(1) 1979HUB/HER (2) 1986LIA/NG(b)

Disulfur anion SK–S (Also see Chapter 26)

(1) 130G10 (2) 92.3G0.3

544G42 386.0G1.4

(1) Derived (2) Derived from EA in ref.

(1) 1974GUR/KAR (2) 1996NIST

Trisulfur S–S2

62.5G1.8, 0 K

261.5G7.7

Derived

2003KRE/SCH

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 8.2 (continued) S–S BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Disulfur oxide SaSO

80.9

338.5

Derived from DfH0 in ref.

1998CHA

Hydrogen disulfur SaSH2

51G7

213.4G29

Review

1978BEN

Difluoro disulfur SaSF2

O57G8

O238.5G34

Review

1978BEN

Dimethyl disulfur SaSMe2

53G4

221.8G17

Review

1978BEN

Hydrogen disulfide HS–SH

64.7G1

270.7G8.4

Derived from DfH0 in ref.

2002CRC

Difluorodisulfane FS–SF

86.6

362.3

Derived from DfH0 in ref.

1998CHA

Dichlorodisulfane ClS–SCl

(1) 46G7 (2) 78.8

192G29 329.7

(1) Derived (2) Derived from DfH0 in ref.

(1) 1978TAK (2) 1996NIST

Chlorodisulfane ClS–S

(1) 68G5

285G21

(1) Derived

(1) 1978TAK

(2) 84.8

354.9

(2) Derived from DfH0 in ref.

(2) 1996NIST

Methanehydrodifulfide CH3S–SH

65.0

272.0

Derived

1999ARM

Alkylhydrodifulfide RS–SH

65.2

272.8

Derived

1999ARM

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BDEs of S–, Se–, Te–, Po–X Bonds

433

Phenyl hydrodisulfide PhS–SH

61G1.5

255.2G6.3

Derived

1978BEN

Dimethyl disulphide CH3S–SCH3

(1) 62.9G2.6

263G11

(1) Mol. beam

(1) 1988PEN/CAO

(2) 64 (3) 65.2G0.9

267.8 272.8G3.8

(2) Electrochemical (3) Fluorescence

(2) 1992NUZ (3) 1992NIC/KRE

Diethyl disulphide C2H5S–SC2H5

66.1

276.6

Derived from DfH0 in ref.

1986PED/NAY

Dipropyl disulphide C3H7S–SC3H7

66.2

277.0

Derived from DfH0 in ref.

1986PED/NAY

Dibutyl disulphide nC4H9S–S–nC4H9

72

301

AOP

1991BAU/FAS

Dialkyl disulphide RS–SR

66.2

277.0

Derived

1999ARM

Methyl phenyl disulphide MeS–SPh

65G1.5

272.0G6.3

Derived

1978BEN

Diphenyl disulphide C6H5S–SC6H5

(1) 47 (2) 51.2G3

196.6 214.2G12.6

(1) 1992NUZ (2) 1986PED/NAY

(3) 55G2 (4) 43 (5) 46G3

230G8.4 180 192.5G12.6

(1) Electrochemical (2) Derived from DfH0 in ref. (3) AOP (4) Derived (5) Calorimetry

Sulfur fluoride F5S–SF5

72.8G5

305G21

Derived from DfH0 in ref.

1996NIST

Hydrogen trisulfide HS–SSH

50G2

209.2G8.4

Derived

1978BEN

(3) 1991BAU/FAS (4) 2000HOF (5) 2005MCD/WEI

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 8.2 (continued) S–S BDEs

The broken bonds (boldfaceZdissociated group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Methyl hydrotrisulfide CH3S–SSH

54G2

225.9G8.4

Derived

1978BEN

Alkyl hydrotrisulfide RS–SSH

54G2

225.9G8.4

Derived

1978BEN

Phenyl hydrotrisulfide PhS–SSH

44G2

184.1G8.4

Derived

1978BEN

Hydrogen tetrasulfide HSS–SSH

33.6G2

140.6G8.4

Derived

1978BEN

Methyl methyl disulfonyl 32.9 dissulfide MeSS–SSMe

137.7

Derived

1986HAW/GRI

Ethyl ethyl disulfonyl dissulfide EtSS–SSEt

32.8

137.2

Derived

1986HAW/GRI

Iso-propyl iso-propyl disulfonyl dissulfide iso-PrSS–SS-iso-Pr

32.0

133.9

Derived

1986HAW/GRI

tert-Butyl tert-butyl disulfonyl dissulfide tert-BuSS–SS-tert-Bu

32.4

135.6

Derived

1986HAW/GRI

Dialkyl tetrasulfide RSS–SSR

33.6G2

140.6G8.4

Derived

1978BEN

Dialkyl polysulfide RS2Cn–S2CmR

33.6G2

140.6G8.4

Derived

1978BEN

7366—CHAPTER 8—6/2/2007—16:55—JEBA—15364—XML MODEL B – pp. 425–454

BDEs of S–, Se–, Te–, Po–X Bonds

435

Hydro disulphide radicals HS–S%

79G1

330.5G4.2

Derived

1978BEN

Methyl disulphide radicals CH3S–S%

83G1

347.3G4.2

Derived

1978BEN

Phenyl disulphide radicals PhS–S%

74G1.5

309.6G6.3

Derived

1978BEN

Alkyl trisulphide radicals RSS–S%

63G1

263.6G4.2

Derived

1978BEN

Alkyl tetrasulphide radicals RSS–S%2

47.5G1

198.7G4.2

Derived

1978BEN

(1) 26.5G0.5 (2) 27.5

(1) 111G2 (2) 115

(1) Equilibrium (2) FT-ICR

(1) 1995DEN/ILL (2) 1998VIS/BIC

(3) FT-ICR

(3) 1996VIS/KON

Equilibrium

1996JAM/ILL

Dialkyl disulfide ions (RS–SR 0 )C% RZMe, R 0 ZMe Me

Et

(2) 26.8

112

Et

Et

(1) 27.5G0.7 (2) 27.5 (3) 27.5G2.3

(1) 115G3 (2) 115 (3) 115G10

Et

n-Pr

(2) 25.6

107

n-Pr

n-Pr

(2) 24.6 (3) 23.3G2.3

(2) 103 (3) 97G10

i-Pr

i-Pr

(2) 33.5

140

n-Bu

n-Bu

(2) 23.2 (3) 21.2G2.3

(2) 97 (3) 89G10

27.5 at 0 K

115

Tetradialkyl disulfide ions (R2SS–SSR2 0 )C RZMe, R 0 ZMe Me,

Et

25.6

107

Et,

Et

28.7

120

n-Pr,

n-Pr

w29.4

w123

7366—CHAPTER 8—6/2/2007—16:55—JEBA—15364—XML MODEL B – pp. 425–454

436

8.3

Comprehensive Handbook of Chemical Bond Energies

S–C bonds

Table 8.3 S–C BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atoms or group)

Methods (reference in parentheses)

kcal/mol

kJ/mol

Carbon monosulfide S–C

(1) 170.2G0.5 (2) 170.7G0.9 (3) 170.5G0.3

712.1G2.3 714.2G2.8 713.3G1.2

MS

(1) 1979COP/REY (1) 1991PRI/ARM (3) 1995COP/DRO

Carbon disulfide SaCS

(1) 104.5G0.5 (2) 104.1G3 (3) 105.0G0.9 (4) 105.3G0.3

437.1G2 435.5G12.6 439.2G3.8 440.6G1.2

(1) MS (2) MS (3) GIB MS (4) Derived from DfH0 in ref.

(1) 1979COP/REY (2) 1980MIL/ERE (3) 1991PRI/ARM (4) 1996NIST

Carbon oxysulfide SaCO

(1) 72.9G0.2

305.1G1.0

(1) 1996NIST

(2) 72.63

303.88

(1) Derived from DfH0 in ref. (2) Derived from data in exited state

Thioformaldehyde SaCH2

131.2

548.9

Derived from DfH0 in ref.

1996NIST

(Methylamino)methanethial SaCNCH3

71

297

Review

1978BEN

Methylthio radical CH3–S

70.2G0.3

293.8G1.4

PD

1999BIS/CHO(b)

Methanethiol HS–CH3

(1) 75G1.5 (2) 74.7G1

313.8G6.3 312.5G4.2

(1) Review (2) Fluorescence

(1) 1978BEN (2) 1992NIC/KRE

Ethene-1-thiol HS–C2H3

83G3

347.3G12.6

Review

1978BEN

7366—CHAPTER 8—6/2/2007—16:55—JEBA—15364—XML MODEL B – pp. 425–454

References

(2) 2005BRO/RAK

BDEs of S–, Se–, Te–, Po–X Bonds

437

Ethanethiol HS–C2H5

73.6G0.5

307.9G2.1

Derived from DfH0 in ref.

1986PED/NAY

1-Propanethiol HS–nC3H7

74.2G0.7

310.5G2.9

Derived from DfH0 in ref.

1986PED/NAY

2-Propanethiol HS–iso-C3H7

73.4G0.9

307.1G3.8

Derived from DfH0 in ref.

1986PED/NAY

1-Butanethiol HS–nC4H9

73.9G0.7

309.2G2.9

Derived from DfH0 in ref.

1986PED/NAY

2-Butanethiol HS–sec-C4H9

73.5G0.7

307.5G2.9

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-1-propanethiol HS–iso-C4H9

74.1G1.1

310.0G4.6

Derived from DfH0 in ref.

1986PED/NAY

2-Methyl-2-propanethiol HS–tert-C4H9

72.0G0.9

301.2G3.8

Derived from DfH0 in ref.

1986PED/NAY

1-Pentanethiol HS–nC5H11

73.5G1.5

307.5G6.3

Derived from DfH0 in ref.

2002CRC

2-Methyl-2-butanethiol HS–C(CH3)2(C2H5)

71.6G1.5

299.6G6.3

Derived from DfH0 in ref.

1986PED/NAY

2,2-Dimethyl-1-propanethiol HS–neo-C5H11

73.7G2.0

308.4G8.4

Derived from DfH0 in ref.

1986PED/NAY

1-Hexanethiol HS–nC6H13

73.2G1.5

306.3G6.3

Derived from DfH0 in ref.

2002CRC

Cyclo-pentanethiol HS–cyclo-C5H9

71.0G1.2

297.1G5.0

Derived from DfH0 in ref.

1986PED/NAY

(continued)

7366—CHAPTER 8—6/2/2007—16:55—JEBA—15364—XML MODEL B – pp. 425–454

438

Comprehensive Handbook of Chemical Bond Energies

Table 8.3 (continued) S–C BDEs

The broken bonds (boldfaceZdissociated atoms or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Cyclo-hexanethiol HS–cyclo-C6H11

72.9G1.4

305.0G5.9

Derived from DfH0 in ref.

1986PED/NAY

Benzenethiol HS–C6H5

86.2G1.5

360.7G6.3

Derived from DfH0 in ref.

1996NIST

Benzenemethanethiol HS–CH2C6H5

61.7G1.5

258.2G6.3

Derived from DfH0 in ref.

1986PED/NAY

Methanethioic S-acid HS–C(O)H

74G2

309.6G8.4

Review

1978BEN

Ethanethioic S-acid HS–C(O)CH3

73.6G1.5

307.9G6.3

Derived from DfH0 in ref.

2002CRC

Dimethyl sulphide CH3S–CH3

(1) 77.2G2 (2) 74.9G1.5 (3) 73.6G0.8

323.0G8.4 313.4G6.3 307.9G3.3

(1) Pyrolysis (2) PD (3) Fluorescence

(1) 1977COL/BEN (2) 1991NOU/NOR (3) 1992NIC/KRE

Iodomethyl methyl sulfide CH3S–CH2I

78.3G2.2

327.6G9.2

Derived from DfH0 in ref.

1996NIST

Ethyl methyl sulphide CH3S–C2H5

72.4G1

302.9G4.2

Derived from DfH0 in ref.

1986PED/NAY

Ethyl methyl sulphide C2H5S–CH3

73.4G1.5

307.1G6.3

Derived from DfH0 in ref.

1986PED/NAY

Methyl propyl sulphide CH3S–C3H7

73.3G1.5

306.7G6.5

Derived from DfH0 in ref.

1986PED/NAY

7366—CHAPTER 8—6/2/2007—16:55—JEBA—15364—XML MODEL B – pp. 425–454

BDEs of S–, Se–, Te–, Po–X Bonds

439

Methyl propyl sulphide C3H7S–CH3

73.9G1.5

309.2G6.3

Derived from DfH0 in ref.

1986PED/NAY

Iso-propyl methyl sulphide CH3S–iso-C3H7

72.4G1.5

302.9G6.3

Derived from DfH0 in ref.

1986PED/NAY

Butyl methyl sulphide CH3S–C4H9

72.8G1.5

304.6G6.3

Derived from DfH0 in ref.

1986PED/NAY

tert-Butyl methyl sulphide CH3S–tert-C4H9

70.4G1.5

294.6G6.3

Derived from DfH0 in ref.

1986PED/NAY

Ethyl propyl sulfide C2H5S–C3H7

72.9G1.5

305.0G6.3

Derived from DfH0 in ref.

2002CRC

Ethyl propyl sulfide C3H7S–C2H5

72.5G1.5

303.3G6.3

Derived from DfH0 in ref.

2002CRC

Ethyl iso-propyl sulfide C2H5S–iso-C3H7

73.4G1.5

307.1G6.3

Derived from DfH0 in ref.

2002CRC

Cyclo-pentyl methyl sulphide CH3S–cyclo-C5H9

70.6G1.5

295.4G6.3

Derived from DfH0 in ref.

1986PED/NAY

Methyl pentyl sulphide CH3S–C5H11

71.9G1.5

300.8G6.3

Derived from DfH0 in ref.

1986PED/NAY

Diethyl sulphide C2H5S–C2H5

72.5G1.5

303.3G6.3

Derived from DfH0 in ref.

1986PED/NAY

Ethyl butyl sulphide C2H5S–nC4H9

73.0G1.5

305.4G6.3

Derived from DfH0 in ref.

1986PED/NAY

tert-Butyl ethyl sulphide C2H5S–tert-C4H9

71.1G1.5

297.5G6.3

Derived from DfH0 in ref.

1986PED/NAY

(continued)

7366—CHAPTER 8—6/2/2007—16:55—JEBA—15364—XML MODEL B – pp. 425–454

440

Comprehensive Handbook of Chemical Bond Energies

Table 8.3 (continued) S–C BDEs

The broken bonds (boldfaceZdissociated atoms or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Dipropyl sulphide C3H7S–C3H7

72.8G1.5

304.6G6.3

Derived from DfH0 in ref.

1986PED/NAY

Methyl phenyl sulphide CH3S–C6H5

85.4G1.5

357.3G6.3

Derived from DfH0 in ref.

1986PED/NAY

Methyl phenyl sulphide C6H5S–CH3

(1) 69.4G2 (2) 66.5G2.5

290.4G8.4 278.2G10.5

(1) VLPP (2) Derived from DfH0 in ref.

(1) 1977COL/BEN (2) 1994PED

Ethyl phenyl sulphide C2H5S–C6H5

84.6G2

354.0G8.4

Derived from DfH0 in ref.

1986PED/NAY

Ethyl phenyl sulphide C2H5–SC6H5

64.5G1.5

269.9G6.3

Derived from DfH0 in ref.

1994PED

Benzyl methyl sulphide CH3S–CH2Ph

(1) 61.4G2 (2) 60.5G1

256.9G8.4 253.1G4.2

(1) VLPP (2) Derived from DfH0 in ref.

(1) 1977COL/BEN (2) 1994PED

Diphenyl sulphide C6H5S–C6H5

(1) 78.3G2.5

327.6G10.5

(1) 1986PED/NAY

(2) 76G2

318G8.4

(1) Derived from DfH0 in ref. (2) AOP

(2) 1991BAU/FAS

54G2

225.9G8.4

AOP

1991BAU/FAS

(1) 52.7

220.5

Photolysis

(1) 2005YAM/ION

(2) 54.7

228.9

Benzyl phenyl sulfide C6H5S–CH2C6H5

Benzophenone derivative C6H5S–CH2C6H4C(O)R RZC6H5 C6H4C6H5

7366—CHAPTER 8—6/2/2007—16:56—JEBA—15364—XML MODEL B – pp. 425–454

(2) 2006YAM/ION

BDEs of S–, Se–, Te–, Po–X Bonds

441

9-Phenylthio methylanthracene S CH2

47G2

196.6G8.4

AOP

1991BAU/FAS

75G2

313.8G8.4

AOP

1991BAU/FAS

24.6G0.2

102.9G0.8

AOP

1992VEN/AMA

Cl

24.0G0.3

100.4G1.3

Br

25.7G0.3

107.5G1.3

Me

23.7G0.3

99.2G1.3

MeO

23.5G0.3

98.3G1.3

NO2

27.0G0.3

113.0G1.3

Methyl hydrodisulfide CH3–SSH

57G1.5

238.5G6.3

Review

1978BEN

Dimethyl disulphide CH3–SSCH3

(1) 56.6 (2) 57.4G1.5

236.8 240.2G6.3

(1) AE (2) PD

(1) 1986HAW/GRI (2) 1990NOU/LIA

Ethyl methyl disulphide C2H5–SSCH3

56.2

235.1

AE

1986HAW/GRI

Iso-propyl methyl disulphide iso-C3H7–SSCH3

54.5

228.0

AE

1986HAW/GRI

Methyl tert-butyl disulphide tert-C4H9–SSCH3

52.6

220.1

AE

1986HAW/GRI

10-Phenylthio-9-methylanthracene S

Tropylium thiophenoxides, substituted Y

S

YZH

(continued)

7366—CHAPTER 8—6/2/2007—16:56—JEBA—15364—XML MODEL B – pp. 425–454

442

Comprehensive Handbook of Chemical Bond Energies

Table 8.3 (continued) S–C BDEs

The broken bonds (boldfaceZdissociated atoms or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Alkyl ethyl disulfide C2H5–SSR

54G1.5

225.9G6.3

Review

1978BEN

Alkyl phenyl disulfide Ph–SSR

69.5G1.5

290.8G6.5

Review

1978BEN

Alkyl ethyl polysulfide R–SnEt

54G1.5

225.9G6.3

Review

1978BEN

Methanesulfenic acid HOS–CH3

68.1G3

284.9G12.6

Derived from DfH0 in ref.

1996HUN/SHE

Dimethyl sulfoxide CH3SO–CH3 DfH0(CH3SO)ZK16G2.4 (K67G10)

(1) 53G2 at 0 K (2) 55.1G2.4

221.8G8.4 230.5G10

(1) Photolysis (2) Derived from DfH0 in ref.

(1) 1973GOL/STR (2) 1996NIST

Methanesulfonic acid HOSO2–CH3

77.5G3

324.3G12.6

Derived from DfH0 in ref.

2000GUT/GAL

Dimethyl sulphone CH3SO2–CH3 DfH0(CH3SO2)ZK57.2 (K239.3)

66.8

279.5

Iodination

1971SOL/BEN

Methyl sulphone radical O2S–CH3

(1) 21.4

89.5

(1) 1971SOL/BEN

(2) 14.94G0.92

62.51G3.85

(1) Derived from DfH0 in ref. (2) Radiolysis

(2) 11.91G0.82

49.83G3.43

68.9G2

288.3G8.4

Derived from DfH0 in ref.

1986PED/NAY

–c-C6H11

Ethyl methyl sulphone CH3SO2–C2H5

7366—CHAPTER 8—6/2/2007—16:56—JEBA—15364—XML MODEL B – pp. 425–454

(2) 1976HOR

BDEs of S–, Se–, Te–, Po–X Bonds

443

Iso-propyl methyl sulphone CH3SO2–iso-C3H7

67.5G2

282.4G8.4

Derived from DfH0 in ref.

1986PED/NAY

Allyl methyl sulphone H3CSO2–C3H5

55G2.5

230.1G10.5

Derived from DfH0 in ref.

1986PED/NAY

Butyl methyl sulphone H3CSO2–nC4H9

71.3G2

298.3G8.4

Derived from DfH0 in ref.

1986PED/NAY

Methyl tert-butyl sulphone H3CSO2–tert-C4H9

67.6G2

282.8G8.4

Derived from DfH0 in ref.

1986PED/NAY

Methyl phenol sulphone H3CSO2–C6H5

82.3G2

344.3G8.4

Derived from DfH0 in ref.

1986PED/NAY

Benzyl methyl sulphone CH3SO2–CH2Ph

57.5G2

240.6G8.4

Derived from DfH0 in ref.

1986PED/NAY

Methylthiocarbonitrile CH3S–CN

97G2

405.8G8.4

Derived from DfH0 in ref.

1986PED/NAY

Methylthiocarbonitrile CH3–SCbN

68.5

286.6

Derived from DfH0 in ref.

1978BEN

Methanisothiocyanate CH3NCaS

71

297

Review

1978BEN

S-Ethyl thioacetate C2H5S–C(O)CH3

76.2G2

318.8G8.4

Derived from DfH0 in ref.

2002CRC

S-Propyl thioacetate C3H7S–C(O)CH3

76.5G2

320.1G8.4

Derived from DfH0 in ref.

1994PED

Pentafluorosulfur trifluoromethane F5S–CF3

(1) 88.8G5

371.5G21

(1) 1996NIST

(2) 93.7G10.3

392G43

(1) Derived from DfH0 in ref. (2) PES

(2) 2001CHI/KEN

(continued)

7366—CHAPTER 8—6/2/2007—16:56—JEBA—15364—XML MODEL B – pp. 425–454

444

Comprehensive Handbook of Chemical Bond Energies

Table 8.3 (continued) S–C BDEs

The broken bonds (boldfaceZdissociated atoms or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Mercaptomethyl radical H2C–SH

91.4G2.0

382.4G8.4

Derived

This volume

Methanedisulfur radical CH3–SS

49.4

206.7

Derived from DfH0 in ref.

1986HOW/GRI

Ethanedisulfur radicals C2H5–SS

48.7

203.8

Derived from DfH0 in ref.

1986HOW/GRI

Propane-2-disulfur radical iso-C3H7–SS

48.4

202.5

Derived from DfH0 in ref.

1986HOW/GRI

2-Methylpropane-2-disulfur radical tert-C4H9–SS

46.9

196.2

Derived from DfH0 in ref.

1986HOW/GRI

Benzendisulfur radicals C6H5–SS

60G2

251.0G8.4

Review

1978BEN

CH3–SC%H2

30.7G2.5

128.4G10.5

Derived from DfH0 in ref.

1996NIST

C6H5–SC%H2

43.0G4

179.9G16.7

7366—CHAPTER 8—6/2/2007—16:56—JEBA—15364—XML MODEL B – pp. 425–454

BDEs of S–, Se–, Te–, Po–X Bonds

8.4

445

S–halogen bonds

Table 8.4 S–Halogen BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Sulfur hexafluoride F–SF5

(1) (2) (3) (4) (5)

Sulfur hexafluoride anion F–SFK 5 (Also see Chapter 27)

91.1G3.2 92.2 100.4G2.4 92.5 at 0 K 93.6

kJ/mol

Methods (reference in parentheses)

References

381.2G13.3 385.8 420G10 386.9 391.6

(1) CL (2) FT-HP MS (3) SPST (4) MS (5) Derived from DfH0 in ref.

(1) (2) (3) (4) (5)

1980KIA/ZAR 1990SIE/AUS 1992TSA/HER(b) 1998MIL/NEG 1998CHA

%42.5G2.9

%178G12

CID

2003LOB/CHE

Sulfur pentafluoride F–SF4

(1) 53.1G6.0 (2) 53.7

222.2G25.1 224.7

(1) CL (2) Derived from DfH0 in ref.

(1) 1980KIA/ZAR (2) 1998CHA

Sulfur pentafluoride anion SF4–FK (Also see Chapter 27)

(1) 43.8 (2) 54.9G2.3

183.3 230G10

(1) ICR (2) CID

(1) 1985LAR/MCM (2) 2003LOB/CHE

Sulfur tetrafluoride F–SF3

(1) 84.1G3.0 (2) 86.0G7.8 (3) 81.1

351.9G12.6 360G33 339.3

(1) CL (2) Ion reactions (3) Derived from DfH0 in ref.

(1) 1980KIA/ZAR (2) 1995MIL/MIL (3) 1998CHA

Sulfur trifluoride F–SF2

(1) 63.1G7.1 (2) 68.4

264G30 286.2

(1) CL (2) Derived from DfH0 in ref.

(1) 1980KIA/ZAR (2) 1998CHA

Sulfur difluoride F–SF

(1) 91.7G4.3 (2) 93.0

383.7G18.0 389.1

(1) CL (2) Derived from DfH0 in ref.

(1) 1980KIA/ZAR (2) 1998CHA

(continued)

7366—CHAPTER 8—6/2/2007—16:56—JEBA—15364—XML MODEL B – pp. 425–454

446

Comprehensive Handbook of Chemical Bond Energies

Table 8.4 (continued) S–Halogen BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Sulfur fluoride F–S

82.1G1.6

343.5G6.7

CL

1980KIA/ZAR

Mercapto fluoride HS–F

54.8

229.5

Derived from DfH0 in ref.

2005HOW/MAY

Sulfur fluochloride ClS–F

63.1

263.8

Derived from DfH0 in ref.

2005HOW/MAY

Trimethyl sulfur pentafluoride CF3SF4–F

!78.4

!328.0

Derived

2002SAI/DRE

Trimethyl sulfur trifluoride CF3SF2–F

!87.6G2.3

!366.6G9.6

Derived

2002SAI/DRE

80.5 86.5

337 362

CL

1980KIA/ZAR

Sulfuryl fluorides F–SO2

(1) 16.1 (2) 65G5 (3) 54.7

67.5 272G21 229

(1) MS (2) Derived (3) CL

(1) 1958REE/DIB (2) 1978TAK (3) 1980KIA/ZAR(b)

F–SO2(F)

(1) 156.8 (2) 81G2 (3) 90.6

656.1 338.9G8 379

Thiazyl fluorides F–S(F)xN xZ0 1 2

91G6 36G7 76G7

380.7G25 150.6G19 318G19

Derived

1973LAR/JOH

F–SClO2

84G10

351G42

Derived

1978TAK

Thionyl fluorides F–SO F–SO(F)

7366—CHAPTER 8—6/2/2007—16:56—JEBA—15364—XML MODEL B – pp. 425–454

BDEs of S–, Se–, Te–, Po–X Bonds

Sulfur dichlorides Cl–S

Cl–SCl

447

(1) 67.5 (2) 57.8

282.6 241.8

(1) (2) (3) (4)

278.8 %187 221.8G17 295.4

66.6 %44.7 53G4 70.6

(1) MS (2) Derived from DfH0 in ref.

(1) 1981KAU/VAH (2) 1998CHA

(3) Derived (4) Spectrometry

(3) 1978TAK (4) 1979KOL/VEL

Sulfur fluochloride Cl–SF

38.8

162.3

Derived from DfH0 in ref.

2005HOW/MAY

Sulfur tetrafluoro chloride Cl–SF4

OK1G5

OK4G21

Derived from DfH0 in ref.

2005HOW/MAY

Sulfur pentafluoro chloride Cl–SF5

!65

!272

IR CL

1980MAL/SET

Chloromethylthio Cl–SCH3

70G3

292.9G12.6

Review

1978BEN

Chlorophenylthio Cl–SC6H5

31G2.5

129.7G10.5

Review

1978BEN

Dichlorodifulfide Cl–SSCl

(1) (2) (3) (4)

213.4G8.4 221.8G4 %193 216.6G8.4

(1) Review (2) Derived (3) Spectrometry (4) Derived from DfH0 in ref.

(1) (2) (3) (4)

Chlorodifulfide Cl–SS

42G3

175.7G12.6

Derived

1978TAK

Thionyl chloride ClS(O)–Cl

(1) 58G2 (2) %53.9

242.7G8 %226

(1) Derived (2) Spectrometry

(1) 1978TAK (2) 1979KOL/VEL

OS–Cl

(1) 51G4

213.4G16.7

51G2 53G1 %46.2 51.8G2

1978BEN 1978TAK 1979KOL/VEL 1996NIST

(continued)

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Table 8.4 (continued) S–Halogen BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Sulfuryl chlorides O2S–Cl

(1) 24G4 (2) %58.3

100G16.7 %244

(1) Derived (2) Spectrometry

(1) 1978TAK (2) 1979KOL/VEL

O2ClS–Cl

46G4

193G16.7

Derived

1978TAK

O2FS–Cl

43G10

180G42

Methyl hydrodifulfide Cl–SSCH3

51G2.5

213.4G10.5

Review

1978BEN

Adduct Cl–S(CH3)2

14G3

58.6G12.6

Fluorescence detect

1992STI/NIC

Adduct Cl–S(O)(CH3)2

17.4G0.7

72.8G2.9

Fluorescence detect

2006NIC/PAR

Chloromethylsulfone Cl–SO2CH3

(1) 70.3 (2) 70

294 293

PAC

(1) 1994CHA/GRI (2) 1999LAA/MUL

Chloroethylsulfone Cl–SO2C2H5

68.3

285.6

Correlation

2005DEN/TUM

Chloropropylsulfone Cl–SO2C2H5

68.3

285.6

Correlation

2005DEN/TUM

Chlorophenylsulfone Cl–SO2Ph

(1) 70.5 (2) 71

295 297

PAC

(1) 1994CHA/GRI (2) 1999LAA/MUL

Sulfur dibromide Br–SBr

62G4

259G17

Review

1978BEN

Sulfur bromide Br–S

52G4

218G17

Review

1978BEN

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BDEs of S–, Se–, Te–, Po–X Bonds

449

Sulfur pentafluoro bromide Br–SF5

!55

!230

IR CL

1980MAL/SET

Dibromodifulfide Br–SSBr

42G4

176G17

Review

1978BEN

Adduct Br–S(CH3)2

(1) w14 (2) 12.2G1

w59 51G4

(1) Est. by exp. (2) Spectroscopy

(1) 1992STI/NIC (2) 2001NAK/GOT

Iodothio I–SH

49.4G2

206.7G8.4

Kinetics

1979HWA/BEN(b)

Iodomethylthio I–SCH3

49.3G1.7

206.3G7.1

VLPP

1983SHU/BEN

8.5

S–P, S–As, and S–Sb bonds

Table 8.5 S–P, S–As, and S–Sb BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Trifluorophosphino-1-thione SaPF3

100

418.4

Review

1973BEN

Trichlorophosphino-1-thione SaPCl3

68

284.5

Review

1973BEN

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 8.5 (continued) S–P, S–As, and S–Sb BDEs

The broken bonds (boldfaceZdissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Tribromophosphino-1-thione SaPBr3

94

393.3

Review

1973BEN

Tricyclohexylphino-1-thione SaPCy3

98

410

Calorimetry

1998CAP/WIX

Tributylhosphino-1-thione SaPBu3

96

402

Calorimetry

1998CAP/WIX

Trimethylhosphino-1-thione SaPMe3

94

393

Calorimetry

1998CAP/WIX

Dimethylphenylphosphino1-thione SaPMe2Ph

93

389

Calorimetry

1998CAP/WIX

Methyldiphenylphosphino-1thione SaPMePh2

91

381

Calorimetry

1998CAP/WIX

Triphenylphosphino-1-thione SaPPh3

88

368

Calorimetry

1998CAP/WIX

Triphenylarsono-1-thione SaAsPh3

70

293

Calorimetry

1998CAP/WIX

Triphenylantimono-1-thione SaSbPh3 (Also see Section 10.1)

67

280

Calorimetry

1998CAP/WIX

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BDEs of S–, Se–, Te–, Po–X Bonds

8.6

451

Se–X bonds

Table 8.6 Se–X BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group) Selenium hydrides Se(H)x–H xZ0

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 75.16G0.23 314.47G0.96 (2) 74.7 312.5

(1) PI (2) Est. by exp.

(1) 1986GIB/GRE (2) 2004HIR/YAN

(1) 79.88G0.18 334.22G0.75 (3) 80.05G0.18 334.93G0.75

(3) Recommended

(3) 1994BER/ELL

Selenophenol C6H5Se–H

(1) 78G4 (2) 72G3

326.4G16.7 301G13

(1) ICR (2) Derived

(1) 1996LEE/LI (2) 2005MCD/WEI

Selenium dimer Se–Se

(1) (2) (3) (4) (5)

301.7G8 311.7G8.4 332.6G0.4 330.5 283.5

MS

(1) (2) (3) (4) (5)

Diphenyl diselenide PhSe–SePh

(1) 66.9G4.5 (2) 41G3

280G19 171.5G12.6

Calorimetry

(1) 1980MOR/WAT (2) 2005MCD/WEI

Selenium fluoride Se–F

(1) 80.7G4.6 (2) 81G10

337.7G19.3 339G42

(1) MS (2) Review

(1) 1970OHA/WAH (2) 1974GUR/KAR

Se(F)x–F xZ4 5

64.6G4.6 72.6G4.6

270.2G19.3 303.9G19.3

Collision ionization

1978COM/REI

Selenium chloride Se–Cl

77

322

Review

1974GUR/KAR

Selenium bromide Se–Br

71G20

297G84

Review

1974GUR/KAR

1

72.1G2 74.5G2.0 79.5G0.1 79.0 67.8

1966BER/CHU 1968COL/DRO 1969UY/DRO 1977DRO/SMO 1996SMI/YAT

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 8.6 (continued) Se–X BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Selenium monoxide Se–O

(1) 112G5 (2) 102.7G1.5

469G21 429.7G6.3

(1) Review (2) MS

(1) 1983PED/MAR (2) 1984SMO/DRO

Selenium monosulfide Se–S

(1) 88.7G1.6 (2) 90.0G1

371.1G6.7 376.4G4

MS

(1) 1977DRO/SMO (2) 1983GRA/WIE

Tellunium mono selenide Se–Te

(1) 70.1 (2) 69.7G1

293.3 291.5G4

MS

(1) 1977DRO/SMO (2) 1983GRA/WIE

Selenium mononitride Se–N

90G15

377G63

Derived

1974GUR/KAR

Selenium phosphide Se–P

86.9G2.4

363.7G10.0

MS

1973DRO/MYE

SeaPBu3

75

314

Calorimetry

1998CAP/WIX

SeaPCy3

75

314

Calorimetry

1998CAP/WIX

SeaPh3

67

280

Calorimetry

1998CAP/WIX

Selenium monocarbide Se–C

141.1G1.4

590.4G5.9

MS

1977SMO/DRO

128.6G3.1 75.5G4.3

538G13 316G18

Review

1994TOM/SUS

Silicon selenides Si(Se)x–Se xZ0 1

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BDEs of S–, Se–, Te–, Po–X Bonds

8.7

453

Te–X bonds

Table 8.7 Te–X BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(1) 62.1G1.6 (2) 64.7G0.4

259.8G6.7 270.7G1.7

(1) FT-ICR (2) UV Spectra

(1) 1989GAL/MAR (2) 2005UND/CHA

(2) 65.0G0.1 (3) 66.2G1.2 (4) 65.0G0.1

272.0G0.4 277.0G5.0 272.0G0.4

(3) Recommended (4) LMR

(3) 1994BER/ELL (4) 1994GIL/TOW

Tellurohenol PhTe–H

%63

%264

Derived

2005MCD/WEI

Tellunium dimer Te–Te

(1) 55.9G2.0 (2) 62.3G0.2 (3) 61.6G1

233.9G8.4 260.7G0.8 257.6G4.1

MS

(1) 1868COL/DRO (2) 1969UY/DRO (3) 1994VIS/BAB

Diphenyl ditelluride PhTe–TePh

33G3

138.1G12.6

Calorimetry

2005MCD/WEI

Tellunium iodide Te–I

46G10

192G42

Review

1974GUR/KAR

Tellunium monoxide Te–O

90G5

377G21

Review

1983PED/MAR

335G42

Review

1974GUR/KAR

293.3 291.5G4

MS

(1) 1977DRO/SMO (2) 1983GRA/WIE

Tellurium hydrides Te(H)x–H xZ0 1

Tellunium monosulfide 80G10 Te–S

Tellunium monotelluride Te–Se

(1) 70.1 (2) 69.7G1

References

(continued)

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Table 8.7 (continued) Te–X BDEs BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Tellurium phosphide Te–P

71.2G2.4

297.9G10.0

MS

1973DRO/MYE

TeaPBu3

52

218

Calorimetry

1998CAP/WIX

Tellunium monoantimonide Te–Sb

(1) 60.9 (2) 66.3G0.9

254.8 277.4G3.8

MS

(1) 1960POR/SPE (2) 1974SUL/ZEH

8.8

Po–X bonds

Table 8.8 Po–X BDEs

The broken bonds (boldfaceZdissociated atom or group) Polonium dimmer Po–Po

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol 44.7

kJ/mol 187

Methods (reference in parentheses) Spectroscopy

References 1979HUB/HER

Note: (1) The data of S–O bonds see the O–S bonds in Chapter 6. (2) The data of S–N bonds see the N–S bonds in Chapter 7. (3) The BDEs in the clusters and complexes of C-, Si-, Ge-, Sn-, and Pb-ions are listed in Chapter 24. (4) The BDEs in the clusters and complexes of N-, P-, As-, Sb-, and Bi-ions are listed in Chapter 25. (5) The BDEs in the clusters and complexes of O-, S-, Se-, Te-, and Po-ions are listed in Chapter 26. (6) The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27.

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chapter nine

BDEs of Si–, Ge–, Sn–, and Pb–X bonds 9.1 Si–X BDEs Table 9.1 Si–X BDEs The broken bonds (boldfaceZdissociated atom or group),

BDEs (boldfaceZ recommended data; reference in parentheses)

DfH0(R), kcal/mol (kJ/mol)

kcal/mol (1) 90.3G1.2

Silane SiH3–H DfH0(R)Z47.9G0.6 (200.4G2.5)

Methods (reference in

kJ/mol 377.8G5.0

parentheses) (1) Iodination

References (1) 1981DON/WAL

(2) 91.8G0.5

384.1G2.1

(2) PIMS detect.

(2) 1991SEE/FEN

(3) 91.7G0.5

383.7G2.1

(3) Recommended

(3) 1994BER/ELL

(4) 91.5G2

382.8G8.4

(4) Review

(4) 1995CHA

(5) 91.8G0.5

384G2

(5) Review

(5) 1998BEC/WAL

(1) Review

(1) 1998BEC/WAL

Silicon radicals SiH2–H

(1) 71.0G2

297G8

SiH–H

(1) 76.7

321

Si–H

(1) 69.8

292

Si–D

(2) 71.0G0.5 (3) 72.3

297.1G1.9 302.5

(2) Re-anal. (3) Spectroscopy

(2) 2004HIR/YAN (3) 1979HUB/HER

(1) 1989WAL

Methyl silane

(1) 89.6G2

374.9G8.4

(1) Iodination

MeSiH2–H

(2) 92.3G3

386.2G12.6

(2) Review

(2) 1995CHA

DfH0(R)Z33.7G1.5

(3) 92.7G1.2

388G5

(3) Revised

(3) 1998BEC/WAL

(1) 89.4G2 (2) 93.5G1.2

374.0G8.4 391G5

(1) Iodination (2) Revised

(1) 1989WAL (2) 1998BEC/WAL

(141G6)

Dimethylsilane Me2SiH–H

(continued)

455

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456

Comprehensive Handbook of Chemical Bond Energies

Table 9.1 (continued) Si–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated atom or group),

reference in parentheses)

DfH0(R), kcal/mol (kJ/mol)

kcal/mol

DfH0(R)Z18.6G1.5

Methods (reference in

kJ/mol

parentheses)

References

(3) 93.7

392

(3) GPA

(3) 2004CHA

Trimethylsilane Me3Si–H

(1) 95.0G0.5

397.5G2.1

(1) FP

(1) 1994KAL/GUT

DfH0(R)Z3.5G0.5

(2) 92.0

385

(2) VLPP

(2) 1994BUL/WAL

(3) 94.6G1.7

396G7

(3) Revised

(3) 1998BEC/WAL

(4) 95.0

397.4

(4) GPA

(4) 2004CHA

(5) 94.7G1.0

396.2G4.2

(5) Derived

(5) 2006DAV/BAE

Me3Si–D

(6) 93.0

389.1

(6) Kinetics

(6) 1981ELL/POT

Disilane H5Si2–H

(1) 86.3G2 (2) 89.1G2

361.1G8.4 373G8

(1) Iodination (2) Revised

(1) 1989WAL (2) 1998BEC/WAL

3-Ethyl-silapentane

(1) 90.1

377.0

(1) PAC

(1) 1987KAM/HAW

(C2H5)3Si–H

(2) 95.1

397.9

(2) Review

(2) 1995CHA

(78G6)

(14.8G2.0)

DfH0(R)Z55.9G2 (234G8)

(3) 96.0

401.7

(3) PAC, revised

(3) 1999LAA/MUL

(4) 94.6G1

396G4

(4) Review

(4) 1998BEC/WAL

378

GPA

2004CHA

(1) 85.3G2

356.9G8.4

(1) PAC

(1) 1987KAM/HAW

(2) 90.3

377.8

(2) Review

(2) 1995CHA

1,1,2,2-Tetramethyl disilane 90.3 (CH3)2SiH(CH3)2Si–H

Pentamethyl disilane (CH3)3Si(CH3)2Si–H

3(1,1-Dimethyl-1silaethyl)-2,2,4,4,tetramethyl-2,3,4-

(3) 91.0

380.7

(3) PAC, revised

(3) 1999LAA/MUL

(4) 89.9G1

376G4

(4) Review

(4) 1998BEC/WAL

(1) 79.0

330.5

(1) PAC

(1) 1987KAM/HAW

(2) 83.9 (3) 84

351.0 351.5

(2) Review (3) PAC, revised

(2) 1995CHA (3) 1999LAA/MUL

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BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

457

trisilapentane ((CH3)3Si)3Si–H

(4) 83.7G1

350G4

(4) Review

(4) 1998BEC/WAL

2,2,3,4,4-Pentamethyl-3-

89.1

372.8

Correlation

1998DEN

86.6

362.3

Correlation

1998DEN

(1) 88.2G1.2

369.0G5

(1) Iodination

(1) 1989WAL

silapentane (tert-Bu)2MeSi–H

3-(tert-Butyl)-2,2,4,4tetramethyl-3silapentane (tert-Bu)3Si–H

1-Phenyl-silaethane C6H5SiH2–H DfH0(R)Z62.1 (260)

(2) 90.1

377.0

(2) Review

(2) 1995CHA

(2) 91.3G1.2

382G5

(3) Revised

(3) 1998BEC/WAL

Trimethylthio

(1) 82.5

345.2

(1) PAC

(1) 1992CHA/GUE

silamethane (CH3S)3Si–H

(2) 87.4

365.7

(2) Review

(2) 1995CHA

(3) 87.0

364.0

(3) PAC, revised

(3) 1999LAA/MUL

Triisopropyl

(1) 85.6

358.2

(1) PAC

(1) 1991CLA/GRI

(2) 90.0

376.6

(2) PAC, revised

(2) 1999LAA/MUL

(1) 91.3G3.1

382.0G13

(1) ICR

(1) 1989WET/SAL

thiosilamethane (iso-PrS)3Si–H

Phenyl methyl silamethane, substituted R1R2MeSi–H R1ZPh R2ZH Ph Ph Ph Ph Ph

F Cl C6F5 Ph3Si tBuCH2

(2) 92.1

385.4

(2) Correlation

(2) 1998DEN

(3) 94.3

394.6

(3) Correlation

(3) 2005DEN/TUM

(2) 90.0

376.6

(3) 92.2

385.8

(2) 89.7

375.5

(3) 91.9

384.7

(2) 83.1

347.7

(3) 85.3

356.9

(2) 87.5

366.2

(3) 89.7

375.4

(continued)

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458

Comprehensive Handbook of Chemical Bond Energies

Table 9.1 (continued) Si–X BDEs BDEs (boldfaceZ

The broken bonds (boldfaceZdissociated

recommended data; reference in parentheses)

atom or group), DfH0(R), kcal/mol (kJ/mol) Me

kcal/mol 3-CF3-

1-Np 1-Np 1-Np 1-Np

(2) 87.1

364.2

(3) 89.2

373.4

C6H5

(2) 87.2

365.0

(3) 89.4

374.2

(2) 88.2

369.2

C6H4

(3) 90.4

378.4

3-MeO-

(2) 87.5

366.2

C6H4

(3) 88.8

371.6

3-CF3C6H4

1-Np

3-MeC6H4

1-Np

kJ/mol

C6H4

3-F-

4-CF3C6H4

Methods (reference in

(2) 88.3

369.6

(3) 90.8

379.9

(2) 86.9

363.6

(3) 89.1

372.8

(2) 88.6

370.7

(3) 90.5

378.8

parentheses)

References

4-MeO-

(2) 86.6

362.4

C6H4

(3) 89.7

375.4

Methyl phenyl

(1) 91.3G2.9

382G12

(1) GPA

(1) 2004CHA

silamethane

(2) 89.7G2.3

375.3G9.6

(2) Derived

(2) 2005FAT/KAS

Dimethyl phenyl

(1) 84.6

354.0

(1) PAC

(1) 1990DIA/DIO

silamethane

(2) 88.7

371.0

(2) Correlation

(2) 1998DEN

(3) 90.1G1.7

377G7

(3) Review

(3) 1998BEC/WAL

(4) 90.9

380.2

(4) Correlation

(4) 2005DEN/TUM

Diphenyl silamethane

(1) 86.0

359.8

(1) PAC

(1) 1990DIA/DIO

Ph2SiH–H

(2) 87.7

366.8

(2) Correlation

(2) 1998DEN

(3) 90.6G1.7

379G7

(3) Review

(3) 1998BEC/WAL

(1) 81.7

341.8

(1) PAC

(1) 1990DIA/DIO

1-Np

PhMeSiH–H

PhMe2Si–H

Diphenyl methyl silamethane Ph2MeSi–H

(2) 87.5

366.2

(2) Correlation

(2) 1998DEN

(3) 86.3G2.4

361G10

(3) Review

(3) 1998BEC/WAL

(4) 89.7

375.4

(4) Correlation

(4) 2005DEN/TUM

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BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

459

Triphenyl silamethane, substituted R3Si–H

(1) 84.1

351.9

(1) PAC

RZC6H5

(2) 86.4

361.8

(2) Correlation

(2) 1998DEN

(3) 88.7G0.5

371G2

(3) Review

(3) 1998BEC/WAL

(2) 89.3

373.6

3-CF3-C6H4

(1) 1990DIA/DIO

Trifluorosilane

(1) 100.1G1.2

418.8G5

(1) Iodination

(1) 1989WAL

SiF3–H DfH0(R)ZK235.9G4.8

(2) 103.2G1.2

432G5

(2) Revised

(2) 1998BEC/WAL

(K987G20)

Trichlorosilane

(1) 91.3G1.2

382.0G5

(1) Iodination

(1) 1989WAL

SiCl3–H

(2) 94.4G1.2

395G5

(2) Revised

(2) 1998BEC/WAL

79.8G2

334G8

Derived from

2002CRC

DfH0(R)ZK77G2 (K322G8)

Tribromosilane

DfH0 in ref.

SiBr3–H

Silicon clusters Si(Si)x–Si xZ0

(1) 74.1

310

(1) Derived from

(1) 1998CHA

DfH0 in ref. 1 2

(1) 96.6 (2) 105.2

404 440

(2) Derived

(2) 1997GIN/VIS

Disilane

(1) %82.7, 0K

%346

Derived

(1) 1991RUS/BER(c)

SiH3–SiH3

(2) 76.7G1

321G4

Disilene

(1) 63.3G1.2

264.8G5.0

SiH2aSiH2

(2) 27.0G2

113G8

Trisilane

74.8G2

313G8

(2) 1998BEC/WAL

Derived

(1) 1991RUS/BER(c) (2) 1998BEC/WAL

Derived

1998BEC/WAL

SiH3–Si2H5

(continued)

7366—CHAPTER 9—3/2/2007—12:20—SHANMUGAM—15365—XML MODEL B – pp. 455–480

460

Comprehensive Handbook of Chemical Bond Energies

Table 9.1 (continued) Si–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated atom or group),

reference in parentheses)

DfH0(R), kcal/mol (kJ/mol) Tetrasilane

Methods (reference in

kcal/mol 73.1

kJ/mol 306

parentheses) Derived

References 1998BEC/WAL

H5Si2–Si2H5

Hexamethyl disialne

(1) 69.1

289.1

(1) Derived

(1) 1971LAP/PED

Me3Si–SiMe3

(2) 80.5 (3) 79.3G2.9

336.8 332G12

(2) Pyrolysis (3) VLPP

(2) 1975DAV/HOW (3) 1994BUL/WAL

(4) 79.7G1.4

333.3G5.8

(4) Derived

(4) 2006DAV/BAE

88.0

368.2

Derived

1981WAL

108.3G6

453.1G25

Derived from

2001LYM/NOD

Hexaphenyl disilane Ph3Si–SiPh3

Disilicon

DfH0 in ref.

hexafluoride F3Si–SiF3

Si–Si2N

69.6G4.1

291G17

Derived from

1997BAB/VIS

DfH0 in ref.

Silicon carbides Si(Si)x–C xZ0

106.8

447

110.2

461

Derived from DfH0 in ref.

1998CHA

1

89.6G1.2

375G5

Derived

1998BEC/WAL

90.1G1.7

377G7

Derived

1998BEC/WAL

Methyl silane SiH3–CH3

2-Silapropane MeSiH2–CH3

7366—CHAPTER 9—3/2/2007—12:20—SHANMUGAM—15365—XML MODEL B – pp. 455–480

BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

Trimethylsilane Me2SiH–CH3

92.5G1.7

461

387G7

Derived

1998BEC/WAL

Tetramethylsilane

(1) 74.4

311.3

(1) Derived

(1) 1971LAP/PED

Me3Si–CH3

(2) 91.6

383

(2) VLPP

(2) 1994BUL/WAL

(3) 94.2G2 (4) 94.4G0.8

394G8 395.1G3.5

(3) Derived (4) Derived

(3) 1998BEC/WAL (4) 2006DAV/BAE

85

355.6

Derived

1990ALL/MCM

103.5

433

Derived

2003BRA/NES

414.2

Pyrolysis

1980DAV/WOO

70

292.9

Pyrolysis

1980DAV/WOO

126.9

531

Derived

2003BRA/NES

34.9G1

146G4

Review

1998BEC/WAL

36.8G2.9

154G12

Review

1998BEC/WAL

2-Methyl-2-silapro-1-ene Me2SiaCH2

(1) 39G6 (2) 38.5G2.9

163G25 161G12

(1) ICR (2) Review

(1) 1990ALL/MCM (2) 1998BEC/WAL

Difluoro-2-silaeth-1-ene

50G5

209G21

ICR

1990ALL/MCM

Trifluoromethyl silane F3Si–CH3

Methyl silane-1,1,1-triol (OH)3Si–CH3

Trimethyl sec-butylsilane 99 Me3Si-sec-Bu

Trimethyl allylsilane Me3Si–C3H5

Phenyl silane-1,1,1-triol (OH)3Si–C6H5

2-Silaeth-1-ene SiH2aCH2

2-Silapro-1-ene MeHSiaCH2

SiF2aCH2

(continued)

7366—CHAPTER 9—3/2/2007—12:20—SHANMUGAM—15365—XML MODEL B – pp. 455–480

462

Comprehensive Handbook of Chemical Bond Energies

Table 9.1 (continued) Si–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated

reference in parentheses)

atom or group), DfH0(R), kcal/mol (kJ/mol) Fluoro-2-silapro-1-ene

Methods (reference in

kcal/mol

kJ/mol

parentheses)

References

45G5

188G21

ICR

1990ALL/MCM

(1) 191.1G3.2

799.6G13.4

(1) Derived from

(1) 1996NIST

MeFSiaCH2

Silicon oxide Si(O)x–O xZ0

DfH0 in ref. 1

3-Oxa-disilapropane

(2) 189.6G3.9

793.2G16.4

(1) 108.6

454.2

(2) Spectroscopy

(2) 1999RED/AHA

131.0

548.1

Derived

2001SCH/BER

132.6G2.0

555G8

Derived

1998BEC/WAL

144.4

604

Derived

2003BRA/NES

122.6G2.6

513G11

Derived

1998BEC/WAL

122.4G2.6

512G11

Derived

1998BEC/WAL

136

569

Derived

1998BEC/WAL

H3Si–OSiH3

2-Methyl-2-silapropan-2ol Me3Si–OH

Silane-1,1,1,1-tetraol (OH)3Si–OH

1-Methyl-1,1-dimethyl-1silaethane Me3Si–OMe

1-Ethoxy-1,1-dimethyl-1silaethane Me3Si–OEt

2,2,6,6-Tetramethyl-4oxa-3,5-disilapentane Me3Si–OSiMe3

7366—CHAPTER 9—3/2/2007—12:20—SHANMUGAM—15365—XML MODEL B – pp. 455–480

BDEs of Si–, Ge–, Sn–, and Pb–X Bonds Silaforaldehyde

463

61.2G6

256G25

Review

1998BEC/WAL

21.3

89

Kinetics

2001BEC/CAN

Silicon nitride

(1) 104.7

437.9

(1) Review

(1) 1968GAY

Si–N

(2) 101.9G3.7

426.4G15.4

(2) Spectroscopy

(2) 1989RAJ

(3) 104.7–111.1

438–465

(3) Mol. bean

(3) 1993NAU/COS

(4) 104.5G2.4

437.1G9.9

(4) Spectroscopy

(4) 2000RED/AHA

37.8G1.4

158.2G5.7

Laser photolysis,

1997KRA/KAL

SiH2aO

Silaketene H2SiaCO

Nitrososilane H3Si–NO D3Si–NO

38.4G1.4

160.8G5.7

Nitroso trimethylsilane

44.8G1.0

187.4G4.2

Me3Si–NO

MS detect.

Laser photolysis,

1995KRA/NII

MS detect.

98.5G2 (1,1-Dimethyl-1silaethyl)-methylamine

412G8

Derived

1998BEC/WAL

408G8

Derived

1998BEC/WAL

108.7

455

Derived

1998BEC/WAL

Si2N–Si

68.6

287

Derived

1997GIN/VIS

Si3–N

141.7

593

Derived

1997GIN/VIS

Fluorosilane

152.5G1.2

638G5

Derived

1998BEC/WAL

Me3Si–NHMe

(1,1-Dimethyl-1-silaethyl)- 97.5G2 dimethylamine Me3Si–NMe2

Tri(1,1-dimethyl-1silaethyl)-amine Me3Si–N(SiMe3)2

SiH3–F

(continued)

7366—CHAPTER 9—3/2/2007—12:20—SHANMUGAM—15365—XML MODEL B – pp. 455–480

464

Comprehensive Handbook of Chemical Bond Energies

Table 9.1 (continued) Si–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated atom or group),

reference in parentheses)

DfH0(R), kcal/mol (kJ/mol) Trimethyl fluorosilane

Methods (reference in

kcal/mol

kJ/mol

parentheses)

References

159.9G4.8

669G20

Derived

1989WAL

Derived

(1) 1998BEC/WAL

Me3Si–F

Tetrafluorosilane SiF3–F

(1) 166.6G1.5

697G6

SiF2–F

(2) 102.4G4

428G17

SiF–F

(2) 160.3G4

670.6G17

Si–F

(2) 137.8G4

576.4G17

OSi–F

31.3

131

OFSi–F

36.1

151

Fluorosilane-1,1,1-triol (OH)3Si–F

166.1

Chlorosilane

109.5G1.7

(2) This volume

Derived

2001HIL/LAU

695

Derived

2003BRA/NES

458G7

Derived

1998BEC/WAL

Derived

SiH3–Cl

Trimethyl chlorosilane

(1) 112.8G2.0

472G8

Me3Si–Cl

(2) 117.1G0.8

490.1G3.2

Tetrachlorosilane SiCl3–Cl

(1) 110.4G2.2

462G9

(2) 111.3G1.0

465.7G4.2

SiCl2–Cl

(2) 67.0G1.0

280.3G4.2

SiCl–Cl

(2) 104.0G1.5

435.1G6.3

Si–Cl

(2) 99.6G1.5

416.7G6.3

OSi–Cl

22.0

92

OClSi–Cl

26.3

110

(1) 1989WAL (2) 2006DAV/BAE

Derived

(1) 1998BEC/WAL (2) 2003HIL/LAU

Derived

7366—CHAPTER 9—3/2/2007—12:20—SHANMUGAM—15365—XML MODEL B – pp. 455–480

2001HIL/LAU

BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

465

Chlorosilane-1,1,1-triol (OH)3Si–Cl

118.3

495

Derived

2003BRA/NES

Bromosilane

89.9G2.2 (2)

376G9

Derived

1998BEC/WAL

Derived

(1) 1989WAL

SiH3–Br

Trimethyl bromosilane

(1) 96.0G2.0

402G8

Me3Si–Br

(2) 101.4G1.0

424.2G4.3

Tetrabromosilane SiBr3–Br

(1) 89.9G5.3

376G22

(2) 88.1G2

368.6G8.4

(2) 53.7G2

224.7G8.4

SiBr2–Br

(2) 2006DAV/BAE

Derived

(1) 1998BEC/WAL (2) 2003HIL/LAU

SiBr–Br

(2) 88.7G2

371.1G8.4

Si–Br

(2) 85.6G2

358.2G8.4

Bromosilane-1,1,1-triol

102.5

429

Derived

2003BRA/NES

71.5G2.0

299G8

Derived

1998BEC/WAL

(1) 76.9

321.7

(1) UV spectrom.

(1) 1979DON/WAL

(OH)3Si–Br

Iodosilane SiH3–I

Trimethyl iodosilane Me3Si–I

(2) 76.7G2.0

320.9G8.4

(2) Derived

(2) 1989WAL

(3) 82.1G1.0

343.6G4.2

(3) Derived

(3) 2006DAV/BAE

Tetraiodosilane SiI3–I

(1) 67.9G6.2

284G26

Derived

(1) 1998BEC/WAL

SiI2–I

(2) 39.1G2

163.6G8.4

SiI–I

(2) 78.5G2

328.4G8.4

Si–I

(2) 58.1G2

243.1G8.4

xZ0

%24

%100

1

%80

%335

(2) This volume

OSi(I)x–I MS

2001HIL/LAU

(continued)

7366—CHAPTER 9—3/2/2007—12:20—SHANMUGAM—15365—XML MODEL B – pp. 455–480

466

Comprehensive Handbook of Chemical Bond Energies

Table 9.1 (continued) Si–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated atom or group),

reference in parentheses)

DfH0(R), kcal/mol (kJ/mol)

Methods (reference in

kcal/mol

kJ/mol

parentheses)

References

Si–Ar

1.40

5.86

Spectroscopy

2002TAO/TES

Si2B–Si

103.3

432

Derived

1997GIN/VIS

Silicon phosphide

86.9

363.6

MS

1972SMO/DEP

79.2

331.4

Derived from

1990PIL

Si–P

Phosphino silane

DfH0 in ref.

H3Si–PH2

Silicon sulfides Si(S)x–S xZ0

(1) 147.9

619

(1) Derived from

(1) 1991GUR/VEY

DfH0 in ref. (2) 148.4

621

(2) Derived from

(2) 1996NIST

DfH0 in ref. 1

(3) 147.5G1.2

617G5

(1) 80.6

337

128.6G3.1

538G13

75.5G4.3

316G18

(3) Derived

(3) 1997TOM/HOP

Review

1994TOM/SUS

Review

1994TOM/SUS

Review

1967DRO/GOL

Silicon selenides Si(Se)x–Se xZ0 1

Silicon tellurides Si(Te)x–Te xZ0 1

Silicon monoxide

92.6G2

388G8

46.8G3.8

196G16

53G10

222G42

dimer (SiO)–SiO

7366—CHAPTER 9—3/2/2007—12:20—SHANMUGAM—15365—XML MODEL B – pp. 455–480

BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

467

Me3Si–GeMe3 –SnMe3

67.7 68.3

283.3 285.8

Derived

1971LAP/PED

(CO)5Mn–SiMe3

60.9

254.7

MS

1973BUR/STO

Note: The BDEs in Si-clusters and on Si-surfaces are listed in Section 24.2.

9.2

Ge–X bonds

Table 9.2 Ge–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated atom or group), DfH0(R), kcal/mol (kJ/mol)

reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Germane

(1) 78.0G1

326.4

(1) VLPP

(1) 1987AGR/SET

GeH3–H,

(2) 82.6G2.4 (3) 85.6G2.1

345.6G10.0 358.2G8.8

(2) VLPP (3) FT-ICR

(2) 1983NOB/WAL (3) 1993DEC/GAL

DfH0(R)Z53G2 (221.8G8.4)

(4) 83.4G2

348.9G8.4

(4) Recommended

(4) 1994BER/ELL

(5) 82.5

345.2

(5) EA

(5) 2001MOR/RIV

GeH2–H

(1) 59

247

(1) PIMS

(1) 1990RUS/SCH

GeH–H

(1) 66

276

Ge–H

(1) 63

264

(2) 62.9G1.2

263.2G4.8

(2) Spectroscopy

(2) 2000RAJ/RAJ(c)

(3) %77

%322

(3) Est. by exp.

(3) 1979HUB/HER

Radicals

Ge–D

Trimethylgermane

(1) 81.7G2.4

341.8G10.0

(1) VLPP

(1) 1979DON/WAL

Me3Ge–H

(2) 82

343.1

(2) AE

(2) 1979JAC

(3) 81.6G0.5

341.4G2.1

(3) PAC

(3) 1991CLA/GRI

(4) 79.8G3.5

333.9G14.6

(4) PEDt.

(4) 1995BRI/SAL

(5) 87.0

364.0

(5) PAC, revised

(5) 1999LAA/MUL

Triethyl germane

(1) 82.3

344.3

(1) PAC

(1) 1991CLA/GRI

(C2H5)3Ge–H

(2) 86.0

359.8

(2) PAC, revised

(2) 1999LAA/MUL

Tri-tert-butyl germane

(1) 82.6

345.6

(1) PAC

(1) 1991CLA/GRI

(tBu)3Ge–H

(2) 88.0

368.2

(2) PAC, revised

(2) 1999LAA/MUL

(continued)

7366—CHAPTER 9—3/2/2007—12:20—SHANMUGAM—15365—XML MODEL B – pp. 455–480

468

Comprehensive Handbook of Chemical Bond Energies

Table 9.2 (continued) Ge–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated atom or group),

reference in parentheses)

DfH0(R), kcal/mol (kJ/mol)

Methods (reference in

kcal/mol

kJ/mol

parentheses)

References

72.9

305.2

Correlation

2002DRO/DEN

80.7

337.5

Correlation

2002DRO/DEN

80.5

336.8

Correlation

2002DRO/DEN

81.6

341.6

Correlation

2002DRO/DEN

77.7

324.9

Correlation

2005DEN/TUM

77.7

324.9

Correlation

2002DRO/DEN

Phenyl germane

(1) 79.2

331.4

(1) PAC

(1) 1991CLA/GRI

PhH2Ge–H

(2) 86.0

359.8

(2) PAC, revised

(2) 1999LAA/MUL

3-(1,1-Dimethyl-1silaethyl)-3-germa2,2,4,4-tetramethyl2,4-disilapentane (Me3Si)3Ge–H

Phenylgermane, substituted (2,4,6-Me3–C6H2) GeH2–H

Diphenylgermane, substituted (2,4,6-Me3–C6H2)2 GeH–H

2-Gema-1phenylfromtane (PhCH2)(C2H5) GeH–H

2-Gema-1,2diphenylethane (PhCH2)(Ph)GeH–H

2-Germa-1,3-diphenyl2-benzylpropane (PhCH2)3Ge–H

7366—CHAPTER 9—3/2/2007—12:21—SHANMUGAM—15365—XML MODEL B – pp. 455–480

BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

469

Diphenyl germane Ph2HGe–H

(1) 79.5

332.6

(1) PAC

(1) 1991CLA/GRI

(2) 85.0

355.6

(2) PAC, revised

(2) 1999LAA/MUL

Triphenyl germane

(1) 80.2

335.6

(1) PAC

(1) 1991CLA/GRI

Ph3Ge–H

(2) 86.0

359.8

(2) PAC, revised

(2) 1999LAA/MUL

(3) 77.1

322.5

(3) Correlation

(3) 2002DRO/DEN

76.5

319.9

Correlation

2005DEN/TUM

81.5

341.0

EA

2001MOR/RIV

82.6

345.6

EA

2001MOR/RIV

2,3,5,6-Tetraphenyl-1, 4-digermin

Ph H

Ge

Ph Ge

H Ph

H H

Ph

Methoxygermane H2Ge(OMe)–H

Dimethoxygermane HGe(OMe)2–H

Germanium dimer Ge(Ge)x–Ge xZ0

(1) 64

268

(1) MS

(1) 1959DRO/MAR

(2) 65.4G5 (3) 66

273.6G20.9 276

(2) MS (3) Review

(2) 1972NEC/SOD (3) 1979MIE/GIN

(4) 63.0G1.7

263.5G7.0

(4) MS

(4) 1986KIN/NAG

(5) 63.2G1.6

264.4G6.8

(5) MS

(5) 2002SHI/BAB

Germanium clusters xZ1

(1) 89

372

(1) MS

(1) 1959DRO/MAR

(2) 77.7G5.2

325G22

(2) Derived from

(2) 2000GIN/BAB

DfH0 in ref. 2

Ge2–Ge2

(1) 128

537

(2) 90.0G7.5

377G32

112

469

MS

1959DRO/MAR

(continued)

7366—CHAPTER 9—3/2/2007—12:21—SHANMUGAM—15365—XML MODEL B – pp. 455–480

470

Comprehensive Handbook of Chemical Bond Energies

Table 9.2 (continued) Ge–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated atom or group),

reference in parentheses)

DfH0(R), kcal/mol (kJ/mol) Digermane

kcal/mol 67.2G3

kJ/mol 281.2G8.4

parentheses) Derived from

References 2002CRC

DfH0 in ref.

H3Ge–GeH3

Hexamethyldigermane

Methods (reference in

67.0

280.3

Derived

1971LAP/PED

61.4

257

Derived

1992CAR

125G3

523G13

Derived from

1991GUR/VEY

Me3Ge–GeMe3

Triphenylgermane, substituted Ph3Ge–GePh3

Germanium fluorides Ge(F)x–F xZ0

DfH0 in ref. 1

139G5

582G21

2

75G12

314G50

3

111G12

464G50

(1) 101G5

423G21

Germanium chlorides Ge(Cl)x–Cl xZ0

(1) Derived from

(1) 1991GUR/VEY

DfH0 in ref. 1

(2) 93.4G2.3

390.8G9.6

(1) 86G5

360G21

(2) w93

w389

(2) MS

(2) 1996HIL/LAU

2

(1) 52G12

218G50

3

(1) 84G12

352G50

(3) 74.1G4.6

310G19

(3) MS

(3) 1972TAM/CZI

107G4.6

448G19

MS

1972TAM/CZI

Trimethylchloro germane (CH3)3Ge–Cl

7366—CHAPTER 9—3/2/2007—12:21—SHANMUGAM—15365—XML MODEL B – pp. 455–480

BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

471

Germanium bromides Ge(Br)x–Br xZ0

83G2

347G8

Derived from

1991GUR/VEY

DfH0 in ref. 1

74G3

310G13

2

40.5G12

170G50

3

68G12

285G50

xZ0

64G6

268G25

1

64G6

268G25

2

27.5G12

115G50

3

51G12

213G50

Germanium iodides Ge(I)x–I Derived from DfH0 in ref.

1991GUR/VEY

Germanium carbide

(1) 109G5

456G21

(1) MS

(1) 1959DRO/MAR

Ge–C

(2) 110 (3) 108.9G2.6

460 455.7G11

(2) Review (3) Re-evaluated

(2) 1970DAR (3) 1998SHI/BAB

xZ1

175

732

MS

1959DRO/MAR

2

155

649

3

148

619

Cl3Ge–CH3

(1) 66.4G4.6

278G19

Derived

(1) 1972TAM/CZI

(CH3)3Ge–CH3

(1) 67.8G3.2 (2) 69.0

284G14 288.7

(1) 55.6G4.6

233G19

XaC2CH3

92.0

385

Ph

86.0

360

CbCPh

125

523

GeSi–C

173

724

Ge2Si–C

155

649

Germanium carbides Ge(Ge)x–C

Cl3Ge–CCl3

(2) 1971LAP/PED

Triphenylgermane, substituted Ph3Ge–X Derived

1992CAR

MS

1959DRO/MAR

(continued)

7366—CHAPTER 9—3/2/2007—12:21—SHANMUGAM—15365—XML MODEL B – pp. 455–480

472

Comprehensive Handbook of Chemical Bond Energies

Table 9.2 (continued) Ge–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated

reference in parentheses)

atom or group), DfH0(R), kcal/mol (kJ/mol)

Methods (reference in

kcal/mol

kJ/mol

parentheses)

References

Germanium silicides Ge(Ge)x–Si xZ0

71

297

1

99

414

2

99

414

GeC–Si

128

537

Ge2C–Si

100

418

C2–Ge

146

611

GeSi–Ge

93

389

Ge2C–Ge

84

352

MS

1959DRO/MAR

MS

1959DRO/MAR

MS

1959DRO/MAR

1998SCH/GIN

Ge2Si–Ge

93

389

GeSiC–Ge

79

331

Ge–Sn

55.0G3.1

230G13

Derived from

Ge(Sn)–Sn

79.8G6.3

334G26

DfH0 in ref.

Me3Ge–SnMe3

69.1

289.1

Derived

1971LAP/PED

(1) 157.6

659

(1) Derived from

(1) 1991GUR/VEY

Germanium oxides Ge(O)x–O xZ0

DfH0 in ref.

1

Triphenylgermane,

(2) 156.0G2

652.7G8.4

(2) MS

(2) 1996KAZ/BOL

(3) 157.8

660.3

(3) Spectroscopy

(3) 1999LEE/SET

(1) 75.9

318

108.7

455

Derived

1992CAR

substituted Ph3Ge–O

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BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

473

Germanium sulfides Ge(S)x–S xZ0

(1) 133.0

556

(1) Derived from

(1) 1991GUR/VEY

DfH0 in ref.

1

Germanium selenide

(2) 127.9G0.7

535G3

(2) Evaluation

(2) 1995OHA/CUR

(3) 127.6G0.7

534G3

(3) Derived

(3) 1997TOM/HOP

(1) 60.0

251

(2) 64.3G4.8

269G20

115.8G0.4

484.7G1.7

Review

1996OHA/ZYW

94.8G0.8

396.7G3.3

MS

1995OHA

50.2G2

210G8

45G3

188.3G12.6

Review

1967DRO/GOL

!1.3

!5.4

Spectroscopy

2003TAO/TES

Ge–Se

Germanium tellurides Ge(Te)x–Te xZ0 1

Germanium monoxide dimer (GeO)–GeO

Ge–Ar

Note: The BDEs in Ge-clusters and on Ge-surfaces are listed in Section 24.3.

9.3

Sn–X bonds

Table 9.3 Sn–X BDEs The broken bonds

BDEs (boldfaceZ recommended data;

(boldfaceZdissociated atom or group),

reference in parentheses)

DfH0(R), kcal/mol (kJ/mol) Tin monohydride

Methods (reference in

kcal/mol

kJ/mol

parentheses)

References

63G4

264G17

Review

1968GAY

82.7

346.0

Correlation

2005DEN/TUM

Sn–H

Stannane H3Sn–H

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 9.3 (continued) Sn–X BDEs The broken bonds (boldfaceZdissociated atom or group),

BDEs (boldfaceZ recommended data; reference in parentheses)

DfH0(R), kcal/mol (kJ/mol)

Methods (reference in

kcal/mol

kJ/mol

parentheses)

References

Trimethylstannane

(1) 74

309.6

(1) PAC

(1) 1991CLA/GRI

Me3Sn–H

(2) 75G3.5

313.8G14.6

(2) PEDt

(2) 1995BRI/SAL

(3) 78.0

326.4

(3) PAC, revised

(3) 1999LAA/MUL

(4) 76.1

318.5

(4) Correlation

(4) 2002DRO/DEN

(5) 77G4

322G17

(5) Derived

(5) 2002BEC/BOG

Tributylstannane

(1) 73.7G2

308.4G8.4

(1) PAC

(1) 1986BUR/MAJ

(nBu)3Sn–H

(2) 78.0 (3) 74.0

326.4 309.6

(2) PAC, revised (3) Correlation

(2) 1999LAA/MUL (3) 2005DEN/TUM

Triphenylstannane

71.0

296.9

Correlation

2005DEN/TUM

Ph3Sn–H

Tin dimer

(1) 45.8G4

191.6G16.7

(1) MS

(1) 1962ACK/DRO

Sn–Sn

(2) 45.2

189

(2) Review

(2) 1979MIE/GIN

(3) 44.7G0.1

187.1G0.3

(3) Spectroscopy

(3) 1988PAK/CAI

(4) 47.0

196.7

(4) Review

(4) 1996SMI/YAT

58.4G6.2

244.3G26

Derived from

2000MEL/SCH

DfH0 in ref.

Tin clusters Sn(Sn)x–Sn xZ3 4

86.1G8.5

360.2G36

5

70.4G11

294.6G46

63.7G7.6

266.5G32

Tin germanides

Tetrachloroditin

Derived from

1998SCH/GIN

DfH0 in ref.

Sn–Sn(Ge)

25.5G1.5

106.8G6.2

MS

2005HIL/ROS

61.6

257.7

MS

1971LAP/PED

Cl2Sn–SnCl2

Hexamethyl ditin Me3Sn–SnMe3

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BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

Triphenylstannane, substituted

475

45.2

189.1

Derived

1992CAR

55.0G3.1

230.1G13

Derived from

1998SCH/GIN

Ph3Sn–SnPh3

Tin germanides Sn–Ge

DfH0 in ref. –Ge(Sn)

Lead, compound with tin(1:1)

79.8G6.3

333.9G26

30.2G1.0

126.3G4.0

Combined

2005GIG/MEL

(1) 111.5G3

466.5G12.5

(1) MS

(1) 1968ZMB/HAS

(2) 113.7G2

476G8

(2) Derived from

(2) 1991GUR/VEY

Sn–Pb

Tin fluorides Sn(F)x–F xZ0

DfH0 in ref. 1

(2) 118.4G3

495G13

2

(2) 51G12

213G50

3

(2) 109G17

456G71

Tin chlorides Sn(Cl)x–Cl xZ0 1

(1) 98G4

410G17

(1) Review

(1) 1974GUR/KAR

(2) 83.7G1

350G8

(2) Spectroscopy

(2) 1993RAJ/PON

(3) 85.7G4

359G17

(3) Derived from

(3) 1991GUR/VEY

DfH0 in ref. 2

(3) 50.5G13

211G55

3

(3) 73G13

305G55

Trimethylstannane

(1) 107

448

substituted Me3Sn–Cl

(2) 101.6G4

425G17

80.6G3

337G13

Derived

(1) 1998GAL/PAU (2) 2002BEC/BOG

Tin bromides, Sn(Br)x–Br xZ0

Derived from

1991GUR/VEY

DfH0 in ref. 1

73.3G3

307G13

(continued)

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476

Comprehensive Handbook of Chemical Bond Energies

Table 9.3 (continued) Sn–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated atom or group),

reference in parentheses)

DfH0(R), kcal/mol (kJ/mol)

kcal/mol

kJ/mol

2

36.2G12

151G50

3

66.3G12

277G50

Trimethylstannane,

Methods (reference in parentheses)

(1) 91.3

382

(2) 91G4

381G17

xZ0

56.2G3

235G3

1

68.7G3

287G13

2

25.5G12

107G50

3

52G12

218G50

(1) 76.7

321

(2) 76.5G4

320G17

(1) 65.4

273.6

(2) 64.0

267.8

(3) 60.5

253

(3) 1992CAR

(4) 70.5G4

295G17

(4) 2002BEC/BOG

60.0

251.0

Derived

1988GRI/KAM

55.4

231.8

Derived

1988GRI/KAM

50.4

210.9

Derived

1988GRI/KAM

substituted Me3Sn–Br

Derived

References

(1) 1998GAL/PAU (2) 2002BEC/BOG

Tin iodides Sn(I)x–I

Trimethylstannane, substituted Me3Sn–I Trimethylstannane, substituted Me3Sn–CH3

2,2-Dimethyl-2-

Derived from DfH0 in ref.

1991GUR/VEY

Derived

(1) 1998GAL/PAU (2) 2002BEC/BOG

Derived

(1) 1971LAP/PED (2) 1988GRI/KAM

stannabutane Me3Sn–Et

2,2,3-Trimethyl-2-stannabutane Me3Sn–iPr

2,2,3,3-Tetramethyl-2stanna-butane Me3Sn–tBu

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BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

477

Triphenylstannane, substituted Ph3Sn–X XZCHCH2

67.4

282

Ph

65.5

274

CbCPh

102.1

427

Derived

1992CAR

2002MEL/GIN

Tin bismuthides Sn(Bi)x–Bi xZ0

46.2G3

193G13

Derived from

1

26.8G4.5

112G19

DfH0 in ref.

2

45.3G5.6

190G23

(1) 126.1G3.0

528G13

(1) Review

(1) 1983PED/MAR

(2) 126.3

528

(2) Derived from

(2) 1991GUR/VEY

Tin oxides Sn(O)x–O xZ0

DfH0 in ref. 1

Trimethylstannane,

(2) 62.0

259

116.6G4

488G17

Derived

2002BEC/BOG

Derived

1992CAR

substituted Me3Sn–OH

Triphenylstannane, substituted Ph3Sn–X XZO OH

81.0

338.9

90.6

379.1

(1) 112G6

469G25

(1) Spectroscopy

(1) 1953BAR/DRU

(2) 111G3.0

464.4G12.6

(2) MS

(2) 1962COL/DRO

(3) 111.6

467

(3) Derived from

(3) 1991GUR/VEY

Tin sulfides Sn(S)x–S xZ0

DfH0 in ref. 1

Tin selenide

(3) 57.0

238

95.9G1.4

401.2G5.9

MS

1964COL/DRO

Sn–Se

(continued)

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478

Comprehensive Handbook of Chemical Bond Energies

Table 9.3 (continued) Sn–X BDEs BDEs (boldfaceZ

The broken bonds

recommended data;

(boldfaceZdissociated

reference in parentheses)

atom or group), DfH0(R), kcal/mol

Methods (reference in

(kJ/mol)

kcal/mol

Tin telluride

kJ/mol

parentheses)

References

80.8G1.5

338.1G6.3

MS

1964COL/DRO

Sn–Ar

!1.2

!5.1

Spectroscopy

2004TAO/DAG

Tin monoxide dimer

67G4

280.0G16.7

Review

1967DRO/GOL

Sn–Te

(SnO)–SnO Note: The BDEs in Sn-clusters and on Sn-surfaces are listed in Section 24.4.

9.4

Pb–X bonds

Table 9.4 Pb–X BDEs The broken bonds (boldfaceZdissociated atom or group),

BDEs (boldfaceZ recommended data; reference in parentheses)

DfH0(R), kcal/mol (kJ/mol) Lead monohydride

Methods (reference in

kcal/mol

kJ/mol

parentheses)

References

%37.5

%157

Spectroscopy

1979HUB/HER

(1) 19.4G1.4

81G6

(1) MS

(1) 1976GIN/COC

Pb–H

Lead dimer Pb–Pb

(2) 19.8

83

(2) Review

(2) 1979MIE/GIN

(3) 20.7G0.2

86.6G0.8

(3) MS

(3) 1981PIT

(4) 20.0

83.8

(4) Review

(4) 1996SMI/YAT

Hexamethyl dilead Me3Pb–PbMe3

54.6

228.4

MS

1971LAP/PED

Tetramethylead

(1) 48.8

204.2

(1) Derived

(1) 1971LAP/PED

(CH3)3Pb–CH3

(2) 57G5

238G21

(2) Derived from DfH0 in ref.

(2) 1996NIST

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BDEs of Si–, Ge–, Sn–, and Pb–X Bonds

479

Tetraethyllead (C2H5)3Pb–C2H5

55G5

230G21

Derived from DfH0 in ref.

1996NIST

Lead, compound with

30.2G1.0

126.3G4.0

Combined

2005GIG/MEL

(1) 84.8G3

355G13

Derived from

(1) 1996NIST

DfH0 in ref.

tin (1:1) Pb–Sn

Lead fluorides Pb(F)x–F xZ0 1

(1) 103.8G3

434G13

2

(2) 30G15

126G63

3

(2) 93G19

389G79

(1) 72.0G12

301G50

(2) 1991GUR/VEY

Lead chlorides Pb(Cl)x–Cl xZ0 1

(1) 74.2G12

310G50

2

(2) 29.5G20

123G84

3

(2) 64.8G20

271G84

Derived from DfH0 in ref.

(1) 1996NIST (2) 1991GUR/VEY

Lead bromides Pb(Br)x–Br xZ0

(1) 59.4G3.5

248.5G14.6

(1) LIF

(1) 1995DRA/SIM

(2) 56.4G10

236G42

(2) Derived from

(2) 1996NIST

DfH0 in ref. 1 2

(1) 66.5G3.5

278.2G14.6

(2) 68.6G11

287G46

(3) 26.8G19

112G80

(3) Derived from

(3) 1991GUR/VEY

DfH0 in ref. 3

(3) 45.4G27

190G113

(1) 46.4G9

194G38

Derived from DfH0 in ref.

Lead iodides Pb(I)x–I xZ0 1

(1) 52.0G10

218G42

2

(2) 17.8G19

75G80

3

(2) 40.6G27

170G113

(1) 1996NIST (2) 1991GUR/VEY

(continued)

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480

Comprehensive Handbook of Chemical Bond Energies

Table 9.4 (continued) Pb–X BDEs The broken bonds (boldfaceZdissociated atom or group), DfH0(R), kcal/mol (kJ/mol)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Lead monoxide

(1) 91.3G3

382.0G12.6

(1) Review

(1) 1983PED/MAR

Pb–O

(2) 89.4

374

(2) Derived from DfH0 in ref.

(2) 1996NIST

Lead dioxide

(1) 43.3

181

(1) Derived from

(1) 1991GUR/VEY

DfH0 in ref.

Pb–O2 (2) !37

!155

(2) PD

(2) 2003CAM/PLA

Lead sulfides Pb(S)x–S xZ0

(1) 80.0G2.8

334.7G11.7

(1) MS

(1) 1962COL/DRO

(2) 82.7G0.4

346.0G1.7

(2) MS

(2) 1969UY/DRO

(3) 95.2

398

(3) Derived from

(3) 1991GUR/VEY

DfH0 in ref. 1

(3) 38.5

161

Lead selenide Pb–Se

72.4G1.0

302.9G4.2

MS

1969UY/DRO

Lead telluride

59.7G2.5

249.8G10.5

MS

1969UY/DRO

Lead antimonide Pb–Sb

38.6G2.5

161.5G10.5

MS

1981ZMB/NEU

Lead bismuthide

(1) 33.9G4

141.8G14.6

MS

(1) 1967ROV/DRO

Pb–Bi

(2) 34.0G0.7

142.4G3.0

Lead monoxide dimer

63G5

263.6G21

Pb–Te

(2) 1982NEU/IHL

Review

1967DRO/GOL

(PbO)–PbO Note: (1) The BDEs in the clusters and complexes of C-, Si-, Ge-, Sn-, and Pb-ions are listed in Chapter 24. (2) The BDEs in the clusters and complexes of N-, P-As-, Sb-, and Bi-ions are listed in Chapter 25. (3) The BDEs in the clusters and complexes of O-, S-, Se-, Te-, and Po-ions are listed in Chapter 26. (4) The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27.

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chapter ten

BDEs of P–, As–, Sb–, Bi–X bonds 10.1 P–X bonds Table 10.1 P–X BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 83.9G0.5

351.0G2.1

(1) PIMS

(1) 1986BER/CUR

(2) 83.9G0.5

351.0G2.1

(2) Recommend.

(2) 1994BER/ELL

(1) 75.9G0.5 (2) 75.3

317.5G2.1 315.1

(1) 1986BER/CUR (2) 1996NIST

P–H P–D

(1) 71.0G0.5 (3) 71.5

297.0G2.1 299.0

(1) PIMS (2) Derived from DfH0 in ref. (3) Review

(3) 1979HUB/HER

Methylphosphine CH3PH–H

77G3

322.2G12.6 GPA

1994SUN/PAN

Octylphosphine CH3(CH2)7PH–H

89.7

375.3

PAC

1999LAA/MUL

Ethylphosphine C2H5PH–H

89.7

375.3

MS

1969BOG/GRI

Phosphine H2P–H

Radicals HP–H

(continued)

481

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482

Comprehensive Handbook of Chemical Bond Energies

Table 10.1 (continued) P–X BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

89.2

373.4

Correlation

2002DRO/DEN

Di(a-CN-propyl)phosphine 88.3 (NC(CH2)3)2P–H

369.5

Correlation

2002DRO/DEN

Dibutylphosphine (CH3(CH2)3)2P–H

89.6

375.0

Correlation

2002DRO/DEN

Diethylphosphine (CH3CH2)2P–H

90.3

377.8

Correlation

2002DRO/DEN

Dioctanylphosphine (n-C8H17)2P–H

89.7

375.3

Correlation

2005DEN/TUM

Di-cyclo-hexylphosphine (cyclo-C6H11)2P–H

86.2

360.6

Correlation

2005DEN/TUM

Review

1992YOO/RUS(b)

a-CN-propylphosphine NC(CH2)3PH–H

Phosphorus clusters P(P)x–P xZ0

116.9

489.1

1

59.0

246.9

2

110.8

463.6

P2–P2

54.7

228.7

PIMS

1977SME/COP

Diphosphine H2P–PH2

61.2

256.1

MS

1969MCA/LOS

Tetrafluorodiphosphine F2P–PF2

40.6–42.0

170–176

Derived

1984BER/GRE

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BDEs of P–, As–, Sb–, Bi–X Bonds

483

Tetrachlorodiphosphine Cl2P–PCl2

58

242.7

MS

1963SAN/MOS

Tetraiododiphosphine I2P–PI2

73.9

309

MS

1969FIN/HAM

(Diethylphosphino) diethyl-phosphine (C2H5)2P–P(C2H5)2

86

359.8

MS

1968GRI/BOG

Phosphino fluoride H2P–F

110.3G2.5

461.5G10.5 Derived from DfH0 in ref.

2000FER/ALC

Phosphorus fluorides F2P–F

(1) 131.3

549

(1) Derived from DfH0 in ref.

(1) 1996NIST

FP–F

(1) 123.2

515

P–F

(1) 107.1 (2) 113G4.6 (3) %96.7

448 473G19 %405

(2) Combined (3) IR CL

(2) 1995LAT/BAL (3) 1995ZHA/SET

(1) 85.0G2

356G8

(1) 1998CHA

(2) %77.7

%325

(1) Derived from DfH0 in ref. (2) Spectrometry

ClP–Cl

(3) 72.8G3

305G13

P–Cl

(1) 73.8 (4) %89.8

Phosphorus bromides Br2P–Br P–Br

Phosphorus triiodide I2P–I

Phosphorus chlorides Cl2P–Cl

(2) 1979KOL/VEL

(3) Derived from DfH0 in ref.

(3) 1989GUR/VEY

309 %376

(4) IR CL

(4) 1995ZHA/SET

(1) !62

!259

IR CL

(1) 1980MAL/SET

(2) %78.7

%329

51.9

217

(2) 1995ZHA/SET

MS

1969FIN/HAM (continued)

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484

Comprehensive Handbook of Chemical Bond Energies

Table 10.1 (continued) P–X BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Carbon phosphide C–P

(1) 122.7G2 513.4G8 (2) 121.3G2.1 507.5G8.8

MS

(1) 1971SMO/MYE (2) 1973KOR/GIN(b)

Silicon phosphide Si–P

86.9

363.6

MS

1972SMO/DEP

Phosphino silane H3Si–PH2

79.2

331.4

Derived from DfH0 in ref.

1990PIL

Phosphorus nitride P–N

147.5G5.0

617.1G20.9 MS

1969GIN(b)

(1) 142.7 (2) 140.8

597.2 589

(1) 1979HUB/HER (2) 1996NIST

(2) 129.1

540

(1) Spectroscopy (2) Derived from DfH0 in ref.

Phosphoryl fluoride OaPF3

(1) 130G5 (2) 129

544G21 534

Review

(1) 1966KER (2) 1973BEN

Phosphoryl chloride OaPCl3

(1) 122G5 (2) 124

510G21 519

Review

(1) 1966KER (2) 1973BEN

Phosphoryl bromide OaPBr3

(1) 119G5 (2) 122

498G21 510

Review

(1) 1966KER (2) 1973BEN

Methyl methylphosphate OaP(CH3)3

139

582

Review

1973BEN

Phosphorus oxides P(O)x–O xZ0

1

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BDEs of P–, As–, Sb–, Bi–X Bonds

485

Ethyl ethylphosphate OaP(OC2H5)3

148

619

Review

1973BEN

Phosphinotris (dimethylamino)-1-one OaP(N(CH3)2)3

128

536

Review

1973BEN

Triphenylphosphino-1-one OaPPh3

130

544

Review

1973BEN

Phosphorus monosulfide S–P

105.6G2.4

442G10

MS

1973DRO/MYE

Trifluorophosphino-1thione SaPF3

100

418

Review

1973BEN

Trichlorophosphino-1thione SaPCl3

68

285

Review

1973BEN

Tribromophosphino-1thione SaPBr3

94

393

Review

1973BEN

Tricyclohexylphino-1thione SaPCy3

98

410

Calorimetry

1998CAP/WIX

Tributylhosphino-1-thione SaPBu3

96

402

Calorimetry

1998CAP/WIX

Trimethylhosphino-1thione SaPMe3

94

393

Calorimetry

1998CAP/WIX

(continued)

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486

Comprehensive Handbook of Chemical Bond Energies

Table 10.1 (continued) P–X BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

93

389

Calorimetry

1998CAP/WIX

Methyldiphenylphosphino- 91 1-thione SaPMePh2

381

Calorimetry

1998CAP/WIX

Triphenylphosphino-1thione SaPPh3

88

368

Calorimetry

1998CAP/WIX

Selenium phosphide SeaP

86.9G2.4

363.7G10.0 MS

1973DRO/MYE

SeaPBu3

75

314

1998CAP/WIX

aPCy3

75

314

aPh3

67

280

Tellurium phosphide Te–P

71.2G2.4

297.9G10.0 MS

1973DRO/MYE

TeaPBu3

52

218

Calorimetry

1998CAP/WIX

(CH3)3P–Al(CH3)3

21

88

Re-anal.

1989HAA

Thallium phosphide Tl–P

50G3

209G13

MS

1978PIA/BAL

Dimethylphenyl phosphino-1-thione SaPMe2Ph

Calorimetry

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BDEs of P–, As–, Sb–, Bi–X Bonds

487

Antimony phosphide Sb–P

85.3G1.0

356.9G4.2

MS

1972KOR/GIN

Bismuth phosphide Bi–P

67.3G3.0

281.7G13

MS

1974GIN/COC

Note: The BDEs in P–B, P–Al, P–Ga, and P–In bonds are listed in Chapter 23.

10.2 As–X bonds Table 10.2 As–X BDEs

The broken bonds (boldfaceZdissociated atom or group) Arsenic hydrides H2As–H

As(H)x–H, radicals xZ0

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (2) (3) (4)

74.9G0.2 76.3G0.2 73.5G3.0 72.6

kJ/mol 313.4G0.8 319.2G0.8 307.5G12.6 303.9

Methods (reference in parentheses) (1) (2) (3) (4)

PIMS Recommend. GPA PI

References (1) (2) (3) (4)

1988BER 1994BER/ELL 1994SUN/PAN 1998RAN/SHU

(1) 64.8G2.8 (2) 65.5G0.7

271.1G11.6 (1) Spectroscopy 274.0G2.9 (2) PIMS

(1) 1968DIX/LAM (2) 1988BER

(2) 67.7G0.2 (3) 52.1

283.2G0.8 218.0

(3) Derived from DfH0 in ref.

(3) 1996NIST

(4) 64.6

270.3

(4) Spectroscopy

(4) 1979HUB/HER

(1) 91.3 (2) 92.2G2.5 (3) 92.2

382 Review 385.8G10.5 385.8

1

(2) 52G2.5

217.6G10.5

2

(2) 93.3G2.5

390.4G10.5

98.0

410

1

As–D

Arsenic clusters As(As)x–As xZ0

Arsenic fluoride As–F

Spectroscopy

(1) 1979MIE/GIN (2) 1992YOO/RUS(b) (3) 1996SMI/YAT

1979HUB/HER (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 10.2 (continued) As–X BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Arsenic chloride As–Cl

107

448

Review

1970DAR

Arsenic iodide As–I

70.9G5.8

296.6G24

MS

1979RUN/ZHU

Arsenic monoxide As–O

115.6G2

484G8

Review

1983PED/MAR

Arsenic monosulfide As–S

90.7G1.5

379.5G6.3

MS

1982LAU/BRI

Arsenic monoselenide As–Se

22.9

96

MS

1966PEL/MIL

OaAsPh3

102.6G7.3

429G31

Calorimetry

1988BAR/BUR

SaAsPh3

70

293

Calorimetry

1998CAP/WIX

Arsenic nitride As–N

116.9G0.5

489G2.1

Spectroscopy

1991RAJ/SEN

Arsenic phosphide As–P

103.6G3

433.5G12.6 MS

1974GIN/COC

Antimony arsenide As–Sb

79.0G1.3

330.5G5.4

1978DRO/SMO

MS

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BDEs of P–, As–, Sb–, Bi–X Bonds

489

10.3 Sb–X bonds Table 10.3 Sb–X BDEs

The broken bonds (boldfaceZdissociated atom or group) Antimony hydrides Sb(H)x–H xZ0

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 57.3G1.0

239.7G4.2

Methods (reference in parentheses)

References

(1) PI

(1) 1993RUS/BER(c)

1

(1) 59.5G0.6

248.9G2.5

2

(2) 68.9G0.5

288.3G2.1

(2) Recommend.

(2) 1994BER/ELL

(1) 71.8G1.0 (2) 72.4 (3) 72.1G1.5

300.4G4.8 303 301.7G6.3

(1) MS (2) Review (3) Review

(1) 1973KOR/GIN (2) 1979MIE/GIN (3) 1992YOO/RUS(b)

Pyrolysis

1991LI/LAR

Antimony clusters Sb(Sb)x–Sb xZ0

1

(3) 53.9

225.5

2

(3) 88.7

371.1

Sb–C3H5

21.6

90.4

Sb–C3H7

30.8

128.9

Lead antimonide Sb–Pb

38.6G2.5

161.5G10.5

MS

1981ZMB/NEU

Antimony fluoride Sb–F

105G23

439G96

Review

1968GAY

Antimony chloride Sb–Cl

86G12

360G50

Review

1968GAY

Antimony bromide Sb–Br

75G14

314G59

Review

1968GAY

Antimony monoxide Sb–O

103.7G10

434G42

Review

1983PED/MAR (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 10.3 (continued) Sb–X BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Antimony monosulfide Sb–S

90.5

378.7

MS

1972FAU/MIT

SaSbPh3

67

280

Calorimetry

1998CAP/WIX

Antimony monotelluride Sb–Te

(1) 60.9 (2) 66.3G0.9

254.8 277.4G3.8

MS

(1) 1960POR/SPE (2) 1974SUL/ZEH

Antimony nitride Sb–N

110G20

460G84

Review

1974GUR/KAR

Antimony phosphide Sb–P

85.3G1.0

356.9G4.2

MS

1972KOR/GIN

Antimony arsenide Sb–As

79.0G1.3

330.5G5.4

MS

1978DRO/SMO

Bismuth antimonide Sb–Bi

60.4G0.9

252.7G3.9

MS

1968KOH/CAR

10.4 Bi–X bonds Table 10.4 Bi–X BDEs

The broken bonds (boldfaceZdissociated atom or group) Bismuth hydrides Bi–H –D

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

%67.7

%283.3

67.8

283.7

Methods (reference in parentheses) Spectroscopy

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References 1975LIN/NIL

BDEs of P–, As–, Sb–, Bi–X Bonds

Bismuth clusters Bi(Bi)x–Bi xZ0

491

(1) 47.8 (2) 47.9G1.8 (3) 48.9

200 200.4G7.5 204.4

Review

(1) 1979MIE/GIN (2) 1992YOO/RUS(b) (3) 1996SMI/YAT

1

(2) 22

92.0

2

(2) 61

255.2

(1) 87.7G3 (2) 87.6G3 (3) 86.2G2.3

367G13 366.5G12.5 360.7G9.6

(1) PI (2) LIF (3) CL

(1) 1992YOO/RUS (2) 1993OBE/PAR (3) 1993CHE/OBE

1

(1) 80.7G3.5

338G15

2

(1) 104G4.6

435G19

71.8G1

300.4G4.2

Derived

1967CUB

1

!58

!242.7

2

O71

O297.1

Bismuth bromide Bi–Br

(1) 63.9 (2) 57.4

267.4 240.2

(1) Calorimetry (2) Spectroscopy

(1) 1968CUB(b) (2) 2000RAJ/RAJ

Bismuth iodide Bi–I

(1) 51.5 (2) 44.9 (3) 44.5G1.4

215.5 188.0 186.1G5.8

(1) Calorimetry (2) Spectroscopy (3) Correlation

(1) 1968CUB (2) 1982RAO/RAO (3) 2004RAJ/RAJ

Bismuth monoxide Bi–O

(1) 81.0G1.4 (2) 80.6G3.0

338.9G5.9 337.2G12.6

(1) MS (2) Review

(1) 1969UY/DRO (2) 1983PED/MAR

Bismuth monosulfide Bi–S

75.4G1.1

315.5G4.6

MS

1969UY/DRO

Bismuth monoselenide Bi–Se

67.0G1.4

280.3G5.9

MS

1969UY/DRO

Bismuth fluorides Bi(F)x–F xZ0

Bismuth chlorides Bi(Cl)x–Cl xZ0

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 10.4 (continued) Bi–X BDEs

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Bismuth telluride Bi–Te

55.5G2.7

232.2G11.3

MS

1969UY/DRO

Bismuth phosphide Bi–P

67.3G3.0

281.7G13

MS

1974GIN/COC

Bismuth antimonide Bi–Sb

60.4G0.9

252.7G3.9

MS

1968KOH/CAR

Bi–Sn(Bi)x xZ0 1 2

46.2G3 26.8G4.5 45.3G5.6

193G13 112G19 190G23

Derived from DfH0 in ref.

2002MEL/GIN

Lead bismuthide Bi–Pb

(1) 33.9G4 (2) 34.0G0.7

141.8G14.6 142.4G3.0

MS

(1) 1967ROV/DRO (2) 1982NEU/IHL

Thallium bismuthide Bi–Tl

28.9G3

120.9G12.6

Review

1974GUR/KAR

Note: (1) The BDEs in the clusters and complexes of CK, SiK, GeK, SnK, and PbKions are listed in Chapter 24. (2) The BDEs in the clusters and complexes of NK, PK, AsK, SbK, and BiKions are listed in Chapter 25. (3) The BDEs in the clusters and complexes of OK, SK, SeK, TeK, and PoKions are listed in Chapter 26. (4) The BDEs in the clusters and complexes of halogenated ions are listed in Chapter 27.

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chapter eleven

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X bonds

11.1

H–, HC–, and HK–X bonds

Table 11.1 BDEs of H–, HD–, and HL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) H–H

kcal/mol

kJ/mol

Methods (reference in parentheses)

435.990 435.7805G0.0010 435.7799G0.0005 435.7799G0.0010 435.7799G0.0001 439.433 439.2229G0.0012 439.2223G0.0002 439.2223G0.0012 440.49 443.533 443.3194G0.0008 443.3194G0.0008 443.3197G0.0003 443.3201G0.0008 444.91 446.67

Spectroscopy

D–T T–T

(1) 104.204 (2) 104.1540G0.0002 (3) 104.1539G0.0001 (4) 104.1539G0.0002 (5) 104.1539G0.0001 (1) 105.027 (3) 104.9768G0.0003 (5) 104.9767G0.0001 (6) 104.9767G0.0003 (1) 105.28 (1) 106.007 (3) 105.9559G0.0002 (4) 105.9559G0.0002 (5) 105.9560G0.0001 (7) 105.9561G0.0002 (1) 106.34 (1) 106.76

ZnO(surf.)D–D

93.8

392.5

IR

H–D

H–T D–D

References (1) 1979HUB/HER (2) 1992BAL/SMI (3) 1993EYL/MEL (4) 1994BAL/SMI (5) 2004ZHA/CHE

(6) 1993BAL/VAL

(7) 1992BAL/STO

2002KAZ/PID

(continued)

493

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Comprehensive Handbook of Chemical Bond Energies

Table 11.1 (continued) BDEs of H–, HC–, and HK–X Bonds

The broken bonds (boldfaceZdissociated fragment) HC–H

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 62.0139G0.0002 (2) 62.0138G0.0001 (2) 62.4049G0.0001 (1) 62.9639G0.0002 (2) 62.9638G0.0001 (3) 62.9639G0.0001

259.4661G0.0010 259.4659G0.0002 261.1021G0.0002 263.4410G0.0008 263.4405G0.0003 263.4410G0.0002

Spectroscopy

HC–H2

(1) 101.2

423.4

(1) 1988LIA/BAR

HC 2 –H

(2) 101.7G0.5 (1) 143.3

425.6G2.0 599.6

(1) Der. from DfH0 in ref. (2) PI

(1) 6.6 (2) 6.9G0.3 (3) 7.01G0.1 (1) 3.1G0.1 (2) 3.3G0.2 (2) 3.2G0.2 (2) 1.72G0.1 (2) 1.64G0.1 (2) 1.54G0.1 (2) 0.88G0.1 (2) 0.80G0.1 (2) 0.61G0.1

27.6 28.9G1.3 29.3G0.4 13.0G0.4 13.8G0.8 13.4G0.8 7.2G0.4 6.9G0.4 6.4G0.4 3.7G0.4 3.3G0.4 2.6G0.4

HP MS

(1) 1983BEU/EHR (2) 1987HIR (3) 1989HIR/MOR(b)

(1) 7.1 (2) 6.9 (3) 7.12G0.3 (1) 3.4 (2) 3.31 (3) 3.48G0.2 (2) 3.16 (3) 3.35G0.2 (2) 1.72 (3) 1.84G0.1 (2) 1.64 (3) 1.82G0.1 (2) 1.54 (3) 1.74G0.1 (2) 0.88 (3) 0.90G0.1 (2) 0.80 (3) 0.81G0.1

29.7 28.9 29.8G1.3 14.2 13.8 14.6G0.8 13.2 14.0G0.8 7.2 7.7G0.4 6.9 7.6G0.4 6.4 7.3G0.4 3.7 3.8G0.4 3.3 3.4G0.4

Equilibrium

(1) 1983BEU/EHR (2) 1987HIR (3) 1989HIR/MOR

HC–D DC–D

HC 3 ðH2 Þx –H2 xZ0 1 2 3 4 5 6 7 8

DC 3 ðD2 Þx –D2 xZ0 1 2 3 4 5 6 7

(1) 1994BAL/SMI (2) 2004ZHA/CHE

(3) 1992BAL/STO

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(2) 1988COS/HEL

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

8

495

(2) 0.61 (3) 0.71G0.1 (3) w0.6

2.6 3.0G0.4 w2.5

HC 3 –Ne

w0.4

w1.7

Review

1994HIR/YAM

HC 2 –Ar

R24

R100

SIFT

1990BED/SMI

(1) 6.69G0.2 (2) 7.5 (3) %6.7 (1) 4.56G0.1 (1) 4.28G0.1 (1) 2.45G0.1 (1) 2.27G0.1 (1) 2.18G0.1 (1) 1.56G0.1 (4) w1.5

28.0G0.8 31.4 %28.0 19.1G0.4 17.9G0.4 10.3G0.4 9.5G0.4 9.1G0.4 6.5G0.4 w6

(1) HP MS (2) SIFT (3) SIFT

(1) 1989HIR/MOR(b) (2) 1990BED/SMI (3) 1994PRA/HAN

(4) Extrapolate

(4) This volume

DC 3 ðArÞx –Ar xZ0 1 2 3 4 5 6 N

(1) 6.95G0.2 (1) 4.80G0.1 (1) 4.44G0.1 (1) 2.44G0.1 (1) 2.27G0.1 (1) 2.17G0.1 (1) 1.56G0.1 (2) w1.5

29.1G0.8 20.1G0.4 18.6G0.4 10.2G0.4 9.5G0.4 9.1G0.4 6.5G0.4 w6

(1) HP MS

1989HIR/MOR(b)

(2) Extrapolate

(2) This volume

HC–O2

K100.98G0.14

K422.50G0.59

Derived

2006RUS/PIN

HC–H2O

166.9

698.3

Derived from DfH0 in ref.

1996NIST

HK–H

w4.4

w18

Derived

1974GUR/KAR

DK–H

47.79G0.48

199.96G2.03

PES

1994SAR/HER

HK–Li

47.40G0.48

198.32G2.03

PES

1994SAR/HER

9

HC 3 ðArÞx –Ar xZ0 1 2 3 4 5 6 N

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 11.1 (continued) BDEs of H–, HC–, and HK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) HK–O2

HK–H2O

kcal/mol

Methods (reference in parentheses)

kJ/mol

(1) 57.3G2.2

239.7G9.2

(2) 56.4G0.5

14.4G1.0

References

236.0G2.1

(1) Der. from DfH0 in ref. (2) Derived

(2) 2003BLA/KAT

60.2G4.2

Ion reactions

1994MIL/VIG

(1) 1996NIST

Note: The data on proton affinities (PA), electro affinities (EA) and ionization energies (IE) are available in 1988LIA/BAR, 1996NIST, and 1998HUN/LIA.

11.2

Li– and LiG–X bonds

11.2.1 Li–X bonds Table 11.2.1 BDEs of Li–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) Li–Li

SLix–Li xZ1 2 3

(1) (2) (3) (4) (5)

Methods (reference in parentheses)

kcal/mol

kJ/mol

25.4G1 26.4G1.5 25.1 25.1 22.7

106.3G4.2 110.4G6.3 105 105.0 95.3

(1) (2) (3) (4) (5)

276.6G8.4 138.5G6.7 212.5G13.4

MS

1994KUD/YOK

66.1G2.0 33.1G1.6 50.8G3.2

Fluorescence MS Review Review Spectroscopy

References (1) (2) (3) (4) (5)

1969VEL/OTT 1976WU 1979MIE/GIN 1996SMI/YAT 1998ROS/CRO

Li–Na

(1) 20.7G1.5 86.6G6.3 (2) 21.1 88.3 (3) 20.837G0.001 87.181G0.001

(1) MS (2) LDF (3) Spectroscopy

(1) 1977ZMB/WU (2) 1982ENG/ENN (3) 1991FEL

Li–K

19.6G1.0

MS

1977ZMB/WU

82.0G4.2

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BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

497

Li–Mg

16.1G1.5

67.4G6.3

MS

1980WU/IHL

Li–Ca

20.3G2.0

84.9G8.4

MS

1983WU/IHL

Li–Sm –Eu –Tm –Yb

46.2G4.5 64.1G3.0 66.0G3.5 34.3G3.0

193.3G18.8 268.1G12.6 276.1G14.6 143.5G12.6

MS

1983NEU/ZMB

Li–Cu

(1) 46.1G2.1 (2) 45.9

192.9G8.8 191.9

(1) MS (2) R2PI

(1) 1974NEU/ZMB(b) (2) 1997BRO/KNI

Li–Ag

(1) 41.5G1.5 (2) 47.5 (3) 44.5

173.6G6.3 198.8 186.1

(1) MS (2) PI (3) R2PI

(1) 1974NEU/ZMB(b) (2) 1995PIL/DUN (3) 1997BRO/KNI

Li–Au

68.0G1.6

284.5G6.7

MS

1974NEU/ZMB(b)

Li–Hg

(1) 3.3 (2) 3.14G0.09

13.8 13.16G0.38

(1) Review (2) Spectroscopy

(1) 1979HUB/HER (2) 1995GRU/LI

Li–Al

18.2

76.1

R2PI

1994BRO/PIL

Li–Ga –In

31.8G3.5 22.1G3.5

133.1G14.6 92.5G14.6

MS

1975GUG/NEU

Li–Ar

(1) w1.9 (2) 1.87

w7.9 w7.82

(1) Review (2) Der. from the data in ref.

(1) 1969SCH (2) 2002KER/MAV

LiF(100, surf.)–He –Ne –Ar

0.2 0.3 1.6G0.2

0.8 1.3 6.8G1.0

Review

1991VID/IHM

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 11.2.1 (continued) BDEs of Li–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Li–Kr –Xe

w2.9 w2.9

w12.1 w12.1

Scattering

1974AUE

Li–H

56.893G0.001

238.039G 0.006

Spectroscopy

1973WAY/STW

Li–D

(1) 57.41 (2) 57.42

240.19 240.24

Spectroscopy

(1) 1974STW/WAY (2) 1975IHL/WU

LiF(100, surf.)–H

0.4, at 0 K

1.7

Scattering

1975FIN/FRA

Li–F –Cl

138G5 112G3

577G21 469G13

Review

1970DAR

Li–Br

(1) 101G5 (2) 100.1G1

423G21 418.8G4.2

(1) Review (2) Photofrag.

(1) 1970DAR (2) 1980SU/RIL

Li–I

(1) 84G3 (2) 82.5G1

351G13 345.2G4.2

(1) Review (2) Photofrag.

(1) 1970DAR (2) 1979SU/RIL

Li–O

(1) 82G4 (2) 79.6G2.0 (3) 81.4G1.5

343G17 333.0G8.4 340.5G6.3

(1) CL (2) Review (3) Review

(1) 1970HER/HER (2) 1983PED/MAR (3) 1984HYN/STE

Li–S

(1) 74.7G1.8 (2) 64.3G1.8

312.5G7.5 269.0G7.5

MS

(1) 1981KIM/ASA (2) 1994KUD/YOK

Li–Sb

41.3G2.4

172.7G10.0

MS

1982NEU/ZMB

7366—CHAPTER 11—3/2/2007—13:13—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

499

Li–Si

67G6

280G25

MS

1978IHL/WU

Li–Pb

18.8G2

78.7G8

MS

1980NEU/IHL

Li–Bi

(1) 34.1G1.4 (2) 35.7

142.7G6 149.4

MS

(1) 1980NEU/IHL (2) 1981PIT

(LiO)–H

(1) 128.2

536.4

(1) Derived from DfH0 in ref.

(1) 1996NIST

Li–OH

(1) 103.0 (2) 104.5G1

431.0 437.2G4

(2) Review

(2) 1984HYN/STE

LiF(100, surf.)–H2

0.4

1.7

Review

1991VID/IHM

Li–O2

(1) 52.6 (2) 70.7

220.1 296

(1) Flames (2) Revised

(1) 1984HYN/STE (2) 1990PLE/RAJ

(LiO)–LiO

92G8

385G33

Review

1967DRO/GOL

(LiOH)–LiOH

58

243

Derived from DfH0 in ref.

1996NIST

Li2–LiH –Li2H

38.5 38.0

161.1 159.0

MS

2004WU/JON

LiI–LiI

41.6G0.3

174.2G1.3

MS

1998BEN/LES

LiF–AlF3 –GaF3 –ScF3 –YF3 –LaF3

70.7 65.4 75.4 w70.7 w60.9

295.9 273.6 315.5 w296 w255

Derived

1985ZHU/NIK

(continued)

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500

Comprehensive Handbook of Chemical Bond Energies

Table 11.2.1 (continued) BDEs of Li–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Li–C2H5

51.3G1

214.6G8.4

47.3G11.5

197.9G16.3

13G2

–nC4H9

Li(DME)x–DME, DMEZdimethyl ether CH3OCH3

Li(DXE)x–(DXE), DXEZCH3O(CH2)2 OCH3

14G4

kJ/mol

Methods (reference in parentheses)

References

Derived from DfH0 in ref.

1996NIST

54.4G8.4

Derived

2005SOH/LI

58.6G16.7

Derived

2005SOH/LI

11.2.2 LiG–X bonds Table 11.2.2 BDEs of LiG–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

LiC–Li

(1) 30G3 (2) 37.7G2.0 (3) 30.4 (4) 32.8G1.5

126G13 157.7G8.4 127.4 137.3G6.3

(1) Derived (2) MS (3) Spectroscopy (4) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1976WU (3) 1983BER/GOL (4) 1996NIST

LiC(Li)x–Li xZ2

27.8G4.3

116.3G18.0

MS

1976WU

(1) 27.7 (2) 26.3 (1) 30.9 (1) 23.8 (2) 25.4

115.8 110.0 129.3 99.4 106.1

Evaporation

(1) 1994BRE/BUS (2) 2001BRE/CAH

LiC(Li)x–Li xZ4 5 6

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BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35

(1) 36.9 (1) 19.1 (1) 30.0 (1) 24.0 (2) 25.6 (1) 27.7 (1) 25.1 (2) 26.5 (1) 28.4 (1) 24.9 (2) 26.3 (1) 28.1 (1) 26.3 (2) 27.4 (1) 30.2 (1) 26.7 (2) 27.7 (1) 31.1 (2) 30.2 (1) 24.0 (2) 25.8 (1) 27.9 (2) 30.2 (1) 25.6 (2) 27.0 (1) 27.7 (1) 26.3 (2) 27.4 (1) 27.0 (2) 27.9 (1) 26.5 (2) 27.7 (1) 27.4 (2) 28.4 (1) 26.7 (2) 27.9 (1) 27.2 (2) 28.1 (1) 27.0 (2) 27.7 (1) 28.1 (2) 28.6 (1) 27.2 (2) 28.1 (1) 28.6 (1) 27.7 (2) 28.1 (1) 28.1 (2) 28.4

501

154.4 80.1 125.4 100.3 107.1 115.8 105.2 111.0 118.7 104.2 110.0 117.7 110.0 114.8 126.4 111.9 115.8 130.3 126.4 100.3 108.1 116.7 126.4 107.1 112.9 115.8 110.0 114.8 112.9 116.7 111.0 115.8 114.8 118.7 111.9 116.7 113.8 117.7 112.9 115.8 117.7 119.6 113.8 117.7 119.6 115.8 117.7 117.7 118.7

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 11.2.2 (continued) BDEs of LiG–X Bonds

The broken bonds (boldfaceZdissociated fragment) 36 37 38 39 40

LiC(Li)x–Li2 xZ2 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 28.1 (2) 28.4 (1) 28.4 (2) 28.6 (1) 27.7 (2) 28.1 (1) 28.6 (1) 26.5

117.7 118.7 118.7 119.6 115.8 117.7 119.6 111.0

(1) 32.3 (1) 34.1 (2) 32.7 (1) 30.2 (2) 31.8 (1) 36.2 (2) 37.8 (1) 31.6 (1) 24.7 (1) 29.5 (2) 31.1 (1) 27.2 (2) 28.8 (1) 28.4 (2) 29.7 (1) 29.1 (2) 30.4 (1) 28.8 (2) 30.2 (1) 28.6 (2) 30.0 (1) 30.0 (2) 31.1 (1) 32.1 (3) 33.2 (1) 32.5 (2) 33.4 (1) 33.4 (1) 30.7 (2) 31.6 (1) 27.4 (2) 29.3 (1) 29.1 (2) 30.4

135.1 142.8 137.0 126.4 133.1 151.5 158.2 132.2 103.2 123.5 130.3 113.8 120.6 118.7 124.5 121.6 127.4 120.6 126.4 119.6 125.4 125.4 130.3 134.1 138.9 136.0 139.9 139.9 128.3 132.2 114.8 122.5 121.6 127.4

Methods (reference in parentheses)

Evaporation

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

References

(1) 1994BRE/BUS (2) 2001BRE/CAH

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 N

LiC(Li2O)x–Li xZ0 1 2 3 4

LiC–He

(1) 28.8 (2) 30.2 (1) 29.5 (2) 30.7 (1) 28.8 (2) 30.9 (1) 29.1 (2) 31.1 (1) 29.5 (2) 31.6 (1) 29.7 (2) 31.8 (1) 29.5 (2) 31.6 (1) 29.7 (2) 31.4 (1) 30.7 (2) 31.8 (1) 30.9 (2) 32.3 (1) 31.4 (2) 32.3 (1) 31.8 (2) 32.3 (1) 31.4 (2) 32.1 (1) 31.8 (2) 32.3 (1) 32.1 (2) 32.5 (1) 31.6 (2) 32.3 (1) 31.8 (2) 32.3 (1) 30.7 (3) 37.5

120.6 126.4 123.5 128.3 120.6 129.3 121.6 130.3 123.5 132.2 124.5 133.1 123.5 132.2 124.5 131.2 128.3 133.1 129.3 135.1 131.2 135.1 133.1 135.1 131.2 134.1 133.1 135.1 134.1 136.0 132.2 135.1 133.1 135.1 128.3 156.9

27.7 !23.0 24.4 26.5 O27.7

(1) 4.0 (2) 2.6 (3) 2.5

503

(3) Extrapolate

(3) This volume

115.8 !96.5 102.3 111.0 O115.8

MS

1997BRE/CAH

16.9 10.8 10.6

(1) Ion mobility (2) Re-analysis (3) Review

(1) 1983TAK (2) 1984VIE (3) 1984GAT

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 11.2.2 (continued) BDEs of LiG–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(4) 2.55 (5) w2.55

10.66 w10.66

(4) Review (5) Review

(4) 1991PET/HAM (5) 1994BIL/GUT

LiC–Ne

(1) 4.2 (2) 3.7 (3) 3.5 (4) 3.66 (5) w3.60

17.7 15.6 14.7 15.32 w15.08

(1) Ion mobility (2) Re-analysis (3) Review (4) Review (5) Review

(1) 1983TAK (2) 1984VIE (3) 1984GAT (4) 1991PET/HAM (5) 1994BIL/GUT

LiC–Ar

(1) 7.9 (2) 13.7 (3) 8.1 (4) 7.9G3.3

33 57.3 33.9 33G14

(1) Spectroscopy (2) Ion mobility (3) Review (4) CID

(1) 1979HUB/HER (2) 1983TAK (3) 1984GAT (4) 1998WAL/SIE

LiC–Kr

(1) 17.3 (2) 10.1 (3) 11.5

72.3 42.2 48.1

(1) Ion mobility (2) Re-analysis (3) Review

(1) 1983TAK (2) 1984VIE (3) 1984GAT

LiC–Xe

(1) 21.7 (2) 13.5 (3) 13.2

90.7 56.4 55.2

(1) Ion mobility (2) Re-analysis (3) Review

(1) 1983TAK (2) 1984VIE (3) 1984GAT

LiC–H

K1.0G2.0

K4.0G8.4

Derived from IP in ref.

1996NIST

LiC–F

(1) w2 (2) 1.7G5

w8 7G21

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

(1) w6 (2) 15.7G3.6 (1) w9 (2) 10G2.5 (1) w11 (2) 12.2G1.5

w25 66G15 w38 41.8G10.6 w46 51.1G6.3

(1) 9.9G4.8 (2) 9.3G2.3

41.5G20.3 38.9G9.6

(1) MS (2) Derived from IP in ref.

(1) 1972HIL (2) 1996NIST

–Cl –Br –I

LiC–O

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BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

LiC–OLi

(1) 75.6G5.1

316.5G21.2

LiC–Sb

31.0G3.3

129.6G13.9

–Bi

21.7G12

91G50

LiC(LiH)x–LiH xZ3 4 5 6 7 8 9 10 11 12 13 14 15 16

49.6 45.9 45.7 47.7 48.0 45.7 46.4 46.1 45.9 48.0 44.0 44.7 46.8 45.2

Li3CðLiHÞx –LiH xZ3 4 5 6 7 8 9 10 11 12 13 14

LiC(LiH)x–(LiH)2 xZ3 4 5 6 7 8 9 10

505

Derived from IP in ref.

1996NIST

207.4 192.0 191.0 199.7 200.7 191.0 193.9 193.0 192.0 200.7 184.3 187.2 195.9 189.1

MS

1996ANT/DUG

47.3 47.3 46.6 47.7 46.8 46.6 45.9 47.5 46.4 45.4 45.9 45.9

197.8 197.8 194.9 199.7 195.9 194.9 192.0 198.8 193.9 190.1 192.0 192.0

MS

1996ANT/DUG

49.1 45.2 47.0 49.3 47.3 45.7 46.1 45.7

205.5 189.1 196.8 206.5 197.8 191.0 193.0 191.0

MS

1996ANT/DUG

(continued)

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

506

Comprehensive Handbook of Chemical Bond Energies

Table 11.2.2 (continued) BDEs of LiG–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) 11 12 13 14 15

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

47.5 45.7 42.4 45.2 45.7

198.8 191.0 177.5 189.1 191.0

LiC 3 ðLiHÞx –ðLiHÞ2 xZ3 4 5 6 7 8 9 10 11 12 13

48.2 47.5 48.0 48.2 47.0 46.1 47.0 47.5 45.4 45.0 45.4

201.6 198.8 200.7 201.6 196.8 193.0 196.8 198.8 190.1 188.1 190.1

MS

1996ANT/DUG

LiC–H2

6.5

27.2

MS

1979WU

LiC(CO)x–CO xZ0 1 2

13.6G3.1 7.9G1.0 8.4G1.0

57G13 33G4 35G4

CID

1998WAL/SIE

LiC–HCN

36.4

152.3

ICR

1978WOO/BEA

LiC(Li2O)x–Li2O xZ3–8

67–74

280–309

Combined

1993BRE/CAH

(1) 34.0 (2) 32.7G3.3 (3) 33.2G2 (1) 25.8

142.3 137G14 139G8 107.9

(1) Equilibrium (2) CID (3) Re-evaluated

(1) 1970DZI/KEB (2) 1997ROD/ARM (3) 1998ROD/ARM

LiC(H2O)x–H2O xZ0

1

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

2 3 4 5 N

(2) 27.2G2.4 (1) 20.7 (2) 22.5G1.0 (1) 16.4 (2) 17.0G1.2 (1) 13.9 (2) 14.3G1.0 (1) 12.1 (2) 15.1G1.2 (4) w10.5

114G10 86.6 94G4 68.6 71G5 58.2 60G4 50.6 63G5 w44

26.5G1 27.0G1.2 26.3G1.4

507

(4) Extrapolate

(4) This volume

111G4 113G5 110G6

Re-evaluated

1998ROD/ARM

20.1–21.4 14.3–15.2 14.1–14.3

83.9–89.7 59.8–63.7 58.9–59.8

BIRD

2004LEM/WIL

19.6–20.8 14.3–15.2 11.3–11.8

82.0–86.8 59.8–63.7 47.3–49.2

BIRD

2004LEM/WIL

(Bet)LiC(H2O)x–H2O xZ0 1 2 BetZ(CH3)3NCCH2C(O)OK

19.1–20.3 15.9–17.1 12.9 12.9

80.1–84.9 66.6–71.4 54.0 54.0

BIRD

2004LEM/WIL

(L)LiC–H2O LZa-methyl-proline N-methyl-proline Proline methyl ester

17.4G0.1 17.2G0.2 17.9G0.1

73.0G0.5 72G1 75.0G0.5

BIRD

2005LEM/BUS

(ROH)LiC–H2O RZCH3 C2H5 n-C3H7

(Val)LiC(H2O)x–H2O xZ0 1 2 ValZ H3NCCH(iC3H7)C(O)OK

(AlaOEt)LiC(H2O)x–H2O xZ0 1 2 AlaOEtZ H2NC(CH3)C(O)OC2H5

(continued)

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

508

Comprehensive Handbook of Chemical Bond Energies

Table 11.2.2 (continued) BDEs of LiG–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(Gln)LiC(H2O)x–H2O xZ0 1 GlnZglutamine

(1) 15.3G0.2 (2) 9.3G0.2

64G1 39G1

BIRD

(1) 2005LEM/BUS(b) (2) 2006LEM/WU

(AsnOMe)LiC(H2O)x–H2O xZ0 1 AsnZasparagine

(1) 15.8G0.2 (2) 8.1G0.7

66G1 34G3

BIRD

(1) 2005LEM/BUS(b) (2) 2006LEM/WU

(GlnOMe)LiC(H2O)x–H2O xZ0 1 GlnZglutamine

(1) 15.1G0.2 (2) 6.9G0.5

63G1 29G2

BIRD

(1) 2005LEM/BUS(b) (2) 2006LEM/WU

(AsnOEt)LiC(H2O)x–H2O xZ0 1 AsnZasparagine

(1) 15.5G0.2 (2) 8.6G0.2

65G1 36G1

BIRD

(1) 2005LEM/BUS(b) (2) 2006LEM/WU

(1) 39.1 (2) 37.3G2 (3) 33.1G1.3 (3) 21.0G0.3 (3) 16.5G0.3 (3) 11.1G0.3 (3) 9.3G0.6 (4) w4.7

163.6 156G8 138.5G5.4 87.9G1.3 69.0G1.3 46.4G1.3 38.9G2.5 w20

(1) ICR (2) Re-analyzed (3) HP MS

(1) 1978WOO/BEA (2) 2004ROD/ARM (3) 1978CAS/HOL

(4) Extrapolate

(4) This volume

LiC–PH3

28G1

117G4

Ion reactions

1977WED/ALL

LiC–AlF4 –GaF4 –ScF4 –YF4 –LaF4

137.3 139.5 144.5 w139.8 w139.8

574.5 583.6 604.5 w585 w585

Derived

1985ZHU/NIK

LiC(NH3)x–NH3 xZ0 1 2 3 4 5 N

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

509

LiC–CH4

31

130

ICR

1975STA/BEA

LiC–CH2F2 –CH3F –CH2Cl2 –CH3Cl

26.5 31 29 25

111 130 121 105

ICR

1975STA/BEA

LiC–CH3OH

(1) 38.1 (2) 37.5G2.0 (3) 37.3G2

159.4 156.8G8.4 156G8

(1) ICR (2) GIB MS (3) Re-evaluated

(1) 1978WOO/BEA (2) 1997ROD/ARM(b) (3) 1998ROD/ARM

(L)LiC–CH3OH LZH2O C2H5OH n-C3H7OH

32.3G1.2 28.2G1.2 26.8G1.4

135G5 118G5 112G6

Re-evaluated

1998ROD/ARM

LiC–HC(O)H

36.0

150.6

ICR

1978WOO/BEA

LiC–CH3CN –CH3NO2 –CH3C(O)H –CH3C(O)OH

43 39.5 41.3 41.5

180 165 173 174

ICR

1975STA/BEA

LiC–CH3NH2 –(CH3)2NH –(CH3)3N

41.1 42.2 42.1

172 177 176

ICR

1978WOO/BEA

LiC–CH3CH2F

34

142

ICR

1975STA/BEA

LiC–C2H5OH

(1) 39.6G1.6 (2) 39.7G2

165.5G6.5 166G8

(1) GIB MS (2) Re-evaluated

(1) 1997ROD/ARM(b) (2) 1998ROD/ARM

33.5G1.2 31.1G1.2 31.1G1.6

140G5 130G5 130G7

Re-evaluated

1998ROD/ARM

(L)LiC–C2H5OH LZH2O CH3OH n-C3H7OH

(continued)

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

510

Comprehensive Handbook of Chemical Bond Energies

Table 11.2.2 (continued) BDEs of LiG–X Bonds

The broken bonds (boldfaceZdissociated fragment) i-C3H7OH n-C4H9OH

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

31.1G1.6 31.8G1.6

130G7 133G10

(1) 39.5 (2) 39.9G2.4 (2) 28.2G1.4 (2) 20.8G1.7 (3) 24.4G0.6 (2) 15.8G2.4

165 167G10 118G6 87G7 102.1G2.5 66G10

LiC–CH3SCH3

32.8

LiC–CH3CCH –CH3CHCH2

LiC–n-C3H7OH

LiC(DME)x–DME, DMEZ dimethyl ether, CH3OCH3 xZ0

Methods (reference in parentheses)

References

(1) ICR (2) CID

(1) 1978WOO/BEA (2) 1996MOR/GLE

(3) FT-ICR

(3) 2000JAR/MIL

137

ICR

1975STA/BEA

28.5 23

119 96

ICR

1975STA/BEA

(1) 41.3G2.1 (2) 41.3G2

172.8G8.6 173G8

(1) GIB MS (2) Re-evaluated

(1) 1997ROD/ARM(b) (2) 1998ROD/ARM

(L)LiC–n-C3H7OH LZH2O CH3OH C2H5OH n-C4H9OH

33.5G1.6 30.8G1.4 33.2G1.6 29.4G2.6

140G7 129G6 139G7 123G11

Re-evaluated

1998ROD/ARM

LiC–i-C3H7F –i-C3H7Cl –i-C3H7Br –i-C3H7I

35.5 30 30.5 29.5

149 126 128 123

ICR

1975STA/BEA

LiC–i-C3H7OH

(1) 41.8G1.8 (2) 41.8G2

174.9G7.5 175G8

(1) GIB MS (2) Re-evaluated

(1) 1997ROD/ARM(b) (2) 1998ROD/ARM

1 2 3

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

511

(L)LiC–i-C3H7OH LZC2H5OH i-C3H7OH n-C4H9OH

33.2G1.6 29.4G1.6 28.4G1.6

139G7 123G7 119G7

Re-evaluated

1998ROD/ARM

LiC–CH3C(O)CH3

44.5

186

ICR

1975STA/BEA

LiC–CH3C(O)OCH3 –(CH3)2NCHO

43.5 50

182 209

ICR

1975STA/BEA

LiC–(CH3)2CCH2

28

117

ICR

1975STA/BEA

LiC–n-C4H9OH

(1) 40.9G2.0 (2) 43.0G2

171.3G8.2 180G8

(1) GIB MS (2) Re-evaluated

(1) 1997ROD/ARM(b) (2) 1998ROD/ARM

(L)LiC–n-C4H9OH LZC2H5OH n-C3H7OH

35.6G2.1 30.8G2.8

149G9 129G12

Re-evaluated

1998ROD/ARM

LiC–i-C4H9OH –s-C4H9OH –t-C4H9OH

40.9G1.8 42.1G2.2 43.0G2.4

171.1G7.6 176.2G8.9 180.1G10.2

Re-evaluated

1998ROD/ARM

LiC(DEE)x–DEE, DEEZdiethyl ether, EtOEt xZ0 2

(1) 41 (2) 15.0G0.4

171.5 62.8G1.7

(1) Derived (2) FT-ICR

2000JAR/MIL

LiC(DXE)x–(DXE), DXEZCH3O(CH2)2OCH3 xZ0 1

58.6G4.3 33.0G2.9

245G18 138G12

CID

1996RAY/FEL

LiC–C4H6

R31

R130

ICR

1977WED/ALL

LiC–cyclo-C6H12

24

100

ICR

1975STA/BEA

(continued)

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

512

Comprehensive Handbook of Chemical Bond Energies

Table 11.2.2 (continued) BDEs of LiG–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(1) 37.9 (2) 39.3G3.3 (2) 24.8G1.7

158.6 164.4G13.6 103.7G7.1

(1) ICR (2) CID

(1) 1978WOO/BEA (2) 2000AMI/ARM

LiC(C6H5F)x–C6H5F xZ0 1

35.8G4.9 22.0G0.8

149.6G20.3 92.1G3.5

CID

2002AMU/ROD

LiC(C6H5OH)x–C6H5OH xZ0 1

43.4G3.9 26.6G0.9

181.6G16.3 111.5G3.7

CID

2002AMU/ROD

LiC(C6H5NH2)x–C6H5NH2 xZ0 1

46.5G5.4 29.8G1.0

194.5G22.5 124.8G4.2

CID

2003ARM/ROD(b)

LiC(C6H5CH3)x–C6H5CH3 xZ0 1

44.6G3.9 27.2G0.8

186.4G16.3 113.7G3.4

CID

2002AMU/ROD(b)

LiC(C6H5OCH3)x–C6H5OCH3 xZ0 1

44.7G4.4 28.3G1.0

187.2G18.5 118.5G4.0

CID

2003AMU/ROD(c)

LiC–C7H7Cl –C7H7Br

R37.3 R14.7

R156 R61.5

ICR

1977WED/ALL

LiC(THF)x–THF, THFZ tetrahydrofuran xZ0 2

(1) 40 (2) 24.1G0.6

167.4 100.8G2.5

(1) Derived (2) FT-ICR

2000JAR/MIL

(1) 54.0 (2) 54.0G1.5

226 226.1G6.2

(1) VG-MS (2) CID

(1) 1996CER/WES (2) 2000ROD/ARM

LiC(C6H6)x–C6H6 xZ0 1

LiC–adenine

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

References

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

–cytosine –guanine

(1) 55.4 (1) 57.1

232 239

(1) 50.4 (2) 51.1G1.5 (2) 56.5G1.7 (3) 55.8G1.7 (2) 53.4G1.6 (3) 52.8G1.7 (1) 51.4 (2) 50.8G1.7 (2) 53.7G1.6 (3) 53.1G1.7 (2) 57.9G1.6 (3) 57.4G1.9 (2) 56.5G1.6 (3) 55.9G1.7 (4) 47.5G1.1 (4) 58.1G2.0 (4) 54.9G1.9 (4) 56.4G1.3

211 213.8G6.1 236.4G7.2 234G7 233.4G6.7 221G7 215 212.4G7.0 224.5G6.6 222G7 242.3G6.6 240G8 236.2G6.5 234G7 198.9G4.8 242.9G8.2 229.6G7.8 235.9G5.3

51.7G1.4 50.9G1.2 41.8G1.1

51.0G1.3 53.1G1.5

513

LiC–uracil, substituted

O

X'

N 3 N1 6 5

X

O

X 0 ZH

XZH 1-Me

H

H

Me

H

5-Me

H

H

6-Me

H

Me

Me

H

5,6-diMe

H

H H H H

5-F 5-Cl 6-Cl 5-Br

H H H H

(1) VG-MS (2) GIB MS

(1) 1996CER/WES (2) 2005YAN/ROD

(3) GIB MS

(3) 2004ROD/ARM

(4) GIB MS

(4) 2004YAN/ROD

216.2G5.7 213.1G5.0 175.1G4.5

CID

2006YAN/ROD

213.3G5.5 222.0G6.2

CID

2006YAN/ROD

LiC–thiouracil, substituted

A NH1

NH 2 3 4 6 5

A'

AZS A 0 ZO O S S S

LiC–thiouracil, substituted

S NH1 5-CH3 6-CH3

NH 2 3 O 4 6 5 CH3

(continued)

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

514

Comprehensive Handbook of Chemical Bond Energies

Table 11.2.2 (continued) BDEs of LiG–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

LiC–1HK1,2,4-triazole –2H-1,2,4-triazole –2H-tetrazole

46.3G1.9 33.0G1.7 36.7G1.6

193.7G7.8 138.2G7.3 153.4G6.6

GIB MS

1999ROD/ARM

LiC–pyrrole –1-methyl-pyrrole –pyrazole –1-methyl-pyrazole –imidazole –1-methyl-imidazole

43.3G4.0 45.4G4.0 45.2G3.9 50.0G4.4 51.0G2.3 58.5G4.9

181.1G16.7 189.8G16.9 189.2G16.2 209.4G18.5 213.2G9.7 244.6G20.3

CID

2002HUA/ROD

LiC–pyridine

(1) 44 (2) 43.3G3.6 (3) 43.7G3.5

184 181G15 183.0G14.5

(1) ICR (2) GIB MS (3) GIB MS

(1) 1975STA/BEA (2) 2000ROD/AMB(b) (3) 2001ROD

46.9G1.6 47.5G3.5 47.4G3.2

196.2G6.7 198.7G14.8 198.2G13.5

GIB MS

2001ROD

56.8G5 48.2G2.4 51.8G4.8

237.8G21.1 201.7G10.0 216.9G20.2

GIB MS

2001ROD(b)

(1) 55.9G2.6 (2) 56.7G2.5 (1) 36.8G2.6 (2) 37.4G2.5 (1) 35.6G3.1 (2) 36.1G3.2

234G11 237.2G10.6 154G11 156.3G10.5 149G13 151.1G13.2

GIB MS

(1) 2000ROD/AMB(b) (2) 2000AMU/ROD

LI+ N

LiC–Y-pyridine

LI+

Y

N YZo-methyl m-methyl p-methyl

LiC–Y-pyridine

LI+ YZo-NH2 m-NH2 p-NH2

Y N

LiC–pyridazine –pyrimidine –pyrazine

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

–1,3,5-triazine

LiC(L)x–L, LZindole xZ0 1

LiC–(12c-4), 12c-4Z 12-crown-4, or c-(CH2O)4

LiC(C10H8)x–C10H8 xZ0 1

LiC(PET)x–PET xZ0 2 4 6 PETZpoly(ethylene terephthalate) oligomer

LiC–cyclo-hexane

LiC–L, a-amino acids LZGly (glycine) Ala (alanine) Asp (asparagine) Cys (cysteine) Glu (glutamic acid) Ile (isolecine) Leu (leucine) Met (methionine) Phe (phenylalanine) Pro (proline)

Ser (serine) Thr (threonine)

515

(1) 30.4G2.6 (2) 30.9G3.0

127G13 129.4G12.6

48.9G2.1 28.6G1.1

204.5G8.7 119.6G4.8

CID

2005RUA/YAN

90.3G12.2

378G51

CID

1996RAY/FEL

45.4G2.9 27.0G1.0

189.8G12.2 113.1G4.3

CID

2003AMU/ROD

10.5 18.9 21.0 26.5

43.9 79.1 87.9 110.9

MALDI

1999GID/WYT

24

100

ICR

1975STA/BEA

(1) 41.6G3 (2) 52.6G2.2 (1) 43.2G3 (1) 51.5G3 (1) 45.2G3 (1) 52.9G3 (1) 45.3G3 (1) 45.2G3 (1) 50.4G3 (2) 76.7G4.1 (1) 48.4G3 (1) 47.5G3 (2) 66.7G2.4 (3) 67.4G2.4 (1) 48.6G3 (1) 49.9G3

174.1G12.6 220G9 180.7G12.6 215.5G12.6 189.1G12.6 221.3G12.6 189.5G12.6 189.1G12.6 210.9G12.6 321G17 202.5G12.6 198.7G12.6 279G10 282G10 203.3G12.6 208.8G12.6

(1) Kinetics (2) CID

(1) 2003FEN/GRO (2) 2004OD/ARM

(3) CID

(3) 2006MOI/ARM

(continued)

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

516

Comprehensive Handbook of Chemical Bond Energies

Table 11.2.2 (continued) BDEs of LiG–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Trp (tryptophan) Tyr (tyrosine) Val (valine)

kJ/mol

Methods (reference in parentheses)

References

(1) 52.3G3 (1) 49.0G3 (1) 45.0G3

218.8G12.6 205.0G12.6 188.3G12.6

LiC–Aze –Pip AzeZazetidine-2-carboxylic acid PipZpipecolic acid

60.5G3.3 65.5G3.8

253G14 274G16

CID

2006MOI/ARM

LiC–L –L2 LZmonopentadecanoin

85.1G6.7 33.0G0.9

356.0G28.0 138.0G3.9

ES/MS/MS

2005HAM/COL

LiC–L –L2 LZ1,3-dipentacanoin

87.2G9.0 33.0G0.2

367.4G37.6 138.0G1.9

ES/MS/MS

2005HAM/COL

LiC–L –L2 LZ1-stearin-2-palmitin glycerol

82.8G4.2 31.8G0.2

346.4G17.6 133.1G1.0

ES/MS/MS

2005HAM/COL

LiK–Li

21.2

88.7

Spectroscopy

1979HUB/HER

11.3

NaK, NaCK and NaK–X bonds

11.3.1 Na–X bonds Table 11.3.1 BDEs of Na–X Bonds

The broken bonds (boldfaceZdissociated fragment) Na–Na

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) 17.49 (2) 18.11

kJ/mol 73.19 75.78

Methods (reference in parentheses) (1) Spectroscopy (2) LIF

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

References (1) 1979HUB/HER (2) 1983VER/BAH

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

517

(3) 18.2 (4) 17.7 (5) 17.879G0.140

76.1 74.2 74.805G0.586

(3) Review (4) Review (5) Spectroscopy

(3) 1988LEE/BYL (4) 1996SMI/YAT (5) 1996JON/MAL

Na2–Na

%12.2

%50.8

LIF

1983GOL/GRE

NaO–Na

(1) 57.8G2 (2) 54.5G2

242G8 228G8

(1) Review (2) Re-analysis

(1) 1984LAM/HIL (2) 1991STE/SCH

O2–Na

58.1G2

243G8

Re-analysis

1991STE/SCH

Na2O–Na

34.1

142.8

PD

1997HAM/KOR

Na–Li

(1) 20.7G1.5 (2) 21.1 (3) 20.837G0.001

86.6G6.3 88.3 87.181G0.001

(1) MS (2) LDF (3) Spectroscopy

(1) 1977ZMB/WU (2) 1982ENG/ENN (3) 1991FEL

Na–K

(1) 15.5G1.0 (2) 15.773G0.002 (3) 15.97

64.9G4.2 65.994G0.008 66.80

Spectroscopy

(1) 1977ZMB/WU (2) 1979BRE/ENG (3) 1999ZEM/STW

Na–Rb

(1) 15.269G0.006 (2) 14.4

63.887G0.024 60.2

Spectroscopy

(1) 1991WAN/KAJ (2) 2001ZEM/STW

Na–Cs

15.1G0.3

63.2G1.3

Spectroscopy

1984DIE/WEI

Na–Cu

42.1G4

176.1G16.7

MS

1973PIA/GIN

Na–Ag

31.8G3

133.1G12.6

Recommended

1979PEL/PIA

NaCl(surf.)–Ag

5.5 (phys)

23.2

SEM

1976DON/ROB

(continued)

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

518

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.1 (continued) BDEs of Na–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NaCl(surf.)–Ag

(1) 9.2 (2) 14.5

38.6 60.8

SEM

(1) 1963WAL/RHO (2) 1976DON/ROB

Na–Au

51.4G3

215.1G12.6

MS

1977PIA/GIN

NaF(surf.)–Au

1.8G1.2 (phys)

7.7G4.8

SEM

1973ROB/ROB

NaF(surf.)–Au

14.5G2.3

60.8G9.6

SEM

1973ROB/ROB

NaCl(surf.)–Au

6.2G1.2 (phys)

26.1G4.8

SEM

1973ROB/ROB

NaCl(surf.)–Au

15.7G2.3

65.6G9.6

SEM

1973ROB/ROB

Na–Cd

2.4

10.2

Spectrometry

1973ZOL

Na–Hg

(1) 2.5 (2) 2.6 (3) 2.6

10.5 10.8 10.8

(1) Spectrometry (2) Scattering (3) Spectroscopy

(1) 1973ZOL (2) 1982HUN/MAI (3) 1991CZU/REB

FNa(100, surf.)–He

0.17

0.73

Review

1991VID/IHM

ClNa(100, surf.)–He

(1) 0.14 (2) 0.16

0.59 0.68

(1) Review (2) HAS

(1) 1991VID/IHM (2) 1997BEN/GLE

Na–Ne

(1) w1.3 (2) w0.9

w5.4 w3.8

Spectrometry

(1) 1977BIT/LAP (2) 1999GIL/TRA

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

519

Na–Ar –Kr

w1.0 w1.08

w4.2 w4.53

Review

1999GIL/TRA

NaCl–Ar

w2

w8

Spectroscopy

1998MIZ/END

Na–Xe

w1.22

w5.12

Review

1999GIL/TRA

ClNa(100, surf.)–Xe

4.6G0.5

19.2G2

HAS

1998GER/GRA

Na–H

(1) 46.6G1.1 (2) 44.38G0.07 (3) 44.68

195.1G4.8 185.69G0.29 186.96

(1) Spectrometry (2) Spectrometry (3) Review

(1) 1983YAN/NEL (2) 1983NED/GIR (3) 1991STW/ZEM

NaF(100, surf.)–H

(1) 0.4, at 0 K (2) 0.4

1.7 1.7

(1) Scattering (2) Review

(1) 1975FIN/FRA (2) 1991VID/IHM

NaCl(100, surf.)–H

(1) (2) (3) (2)

2.0 2.2 2.2 2.9

(1) Scattering (2) Scattering (3) Review

(1) 1982BAE/HOI (2) 1985IAN/SCO (3) 1992VID/IHM

–D

0.5, at 0 K 0.5 0.5 0.7

Na–F

114.1

477.3

Spectroscopy

1979HUB/HER

Na–Cl

98.5G2

412.1G8.4

Photofrag.

1980SU/RIL(b)

Na2–Cl

98.9

413.8

PI

1983PET/DAO

Na–Br

(1) 86.8 (2) 86.8G1

363.1 363.1G4.2

Photofrag.

(1) 1979VAN/VRI (2) 1980SU/RIL

Na–I

(1) 73.3 (2) 72.7G0.5

306.8 304.2G2.1

Photofrag.

(1) 1979VAN/VRI (2) 1979SU/RIL

(continued)

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

520

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.1 (continued) BDEs of Na–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Na–O

(1) (2) (3) (4)

Na2–O

67G3 61.2G4.0 60.2G1 64.5G1

Methods (reference in parentheses)

kJ/mol

CL Review Review Re-analysis

References

280G13 256.1G16.7 252G4 270G4

(1) (2) (2) (3)

98.6

412.5

PI

1983PET/DAO

(NaO)–H

(1) 119.4

499.6

(1) Derived from DfH0 in ref.

(1) 1996NIST

Na–OH

(1) 81.8 (2) 78.9G2

342.3 330.1G8

(2) Review

(2) 1984HYN/STE

Na–NaCl

19.7

82.4

PI

1983PET/DAO

Na–O2

(1) !44 (2) !47.8

!184 !200

(1) Review (2) MS

(1) 1984HYN/STE (2) 1993HIL/LAU

ClNa(100, surf.)–para-H2 (1) 0.7G0.2 (2) 0.7G0.2 –ortho-H2 (2) 0.9G0.2

3.0G0.8 3.0G1.0 3.7G1.0

(1) Induced IR (2) FTIR

(1) 1993DAI/EWI (2) 1998BRI/PIC

ClNa(100, surf.)–HD –D2

0.9G0.2 0.8G0.2

3.6G0.8 3.5G0.8

Induced IR

1993DAI/EWI

NaCl(100, surf.)–HD

0.4G0.1

1.7G0.5

Induced IR

1994DAI/EWI

NaCl(surf.)–CO

3.1G0.7

13G3

IR

1987RIC/BAU

NaCl(100, surf.)–H2O

13.9–15.1

58–63

HAS

1995BRU/GLE

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

(1) (2) (3) (4)

1970HER/HER 1983PED/MAR 1984LAM/HIL 1991STE/SCH

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

NaCl(100, surf.)–CO2

0.7G0.1 (phys)

3.0G0.1

FTIR

1992HEI/KAM

NaCl(100, surf.)–CO2

7.7G0.3

32.4G1.1

FTIR

1992HEI/KAM

NaOH–CO2

w29G5

w121G21

Derived

1991HIL/LAU

NaCl(100, surf.)–OCS

6.0

25.1

HAS

1996GLE/TOE

(NaOH)–NaOH

50.5

211

Derived from DfH0 in ref.

1996NIST

NaF–AlF3 –GaF3 –ScF3 –YF3 –LaF3

81.5 75.4 78.2 w80.0 w76.0

341.2 315.5 327.0 w334.6 w317.8

Derived

1985ZHU/NIK

NaBr–DyBr3 NaI–DyI3

57.5G5 50G10

240.6G21 209G42

MS

2005HIL/LAU

NaDyBr4–NaDyI4 NaDyBr4–NaDyBr2I2

4.9G5 1.9G5

21G21 8G21

MS

2005HIL/LAU

Na(DME)x–DME, 1G1 DMEZdimethyl ether, CH3OCH3

4G4

Derived

2005SOH/LI

Na(DXE)x–(DXE), DXEZ CH3O(CH2)2OCH3

13G4

Derived

2005SOH/LI

3G1

7366—CHAPTER 11—3/2/2007—13:14—SHANMUGAM—15367—XML MODEL B – pp. 493–569

521

522

Comprehensive Handbook of Chemical Bond Energies

11.3.2 NaC– X bonds Table 11.3.2 BDEs of NaD–X Bonds BDEs The broken bonds (boldfaceZdissociated fragment) NaC–Na

(boldfaceZrecommended

Methods

data; reference in parentheses) kcal/mol

(reference in

kJ/mol

parentheses)

References

(1) 23.5

98.5

(1) PI

(1) 1981LEU/HOF

(2) 24.4 (3) 23.5

102.1 98.3

(2) Review (3) Review

(2) 1988LEE/BYL (3) 1996SMI/YAT

(4) Derived from IP

(4) 1996NIST

(4) 23.58G0.07 98.64G0.29

in ref.

NaC(Na)x–Na xZ1

31.8

133.1

2

13.4

56.0

3 4

20.1 13.8

83.9 57.9

5

26.3

110.0

6

17.5

73.3 126.4

7

30.2

9

18.0

75.3

10

15.7

65.6

11

20.8

86.8

12 13

16.6 18.2

69.5 76.2

14

15.9

66.6

15

18.9

79.1

16

19.8

83.0

17

20.8

86.9

18

19.6

82.0

19

21.4

89.7

22 23

17.1 18.9

71.4 79.1

24

18.2

76.2

25

19.4

81.0

26

18.2

76.2

27

20.1

84.1

28

19.8

83.0

29

20.5

85.9

30 31

19.4 21.0

81.0 87.8

32

21.2

88.8

33

21.9

91.6

34

19.6

82.0

35

20.8

86.8

PD

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

1989BRE/CAH

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

523

NaC(Na)x–Na2 xZ2

(1) 17.1

71.5

4 6

(1) 21.9 (1) 30.2

91.6 126.4

(1) PD

(1) 1989BRE/CAH

8

(1) 13.8

57.7

10

(1) 19.4

81.2

12

(1) 18.7

78.2

N

(2) w23.2

w97

(2) Extrapolate

(2) This volume

22.9G0.9

95.8G3.9

Derived from IP in

1996NIST

NaC–Li

ref.

NaC–He

(1) 2.3

9.5

(1) Ion mobility

(2) 1.7

7.0

(2) Re-analysis

(1) 1983TAK (2) 1984VIE

(3) 2.1

8.7

(3) Review

(3) 1984GAT

(4) 1.80

7.55

(4) Review

(4) 1991PET/HAM

(5) w1.70

w7.13

(5) Review

(5) 1994GIL/GUT

NaCClK(surf.)–He

6.2G0.5

26.1G1.9

Scattering

1994HOC/TOE

NaC–Ne

(1) 2.4

10.1

Review

(1) 1984VIE

(2) 2.6

11.1

(2) 1984GAT

(3) 2.52

10.54

(3) 1991PET/HAM

(4) w2.38

w9.04

(4) 1999GIL/TRA

NaC–Ar

NaC–Kr

NaC–Xe

(1) 5.8

24.1

(1) Ion mobility

(1) 1983TAK

(2) 5.3 (3) 4.6

22.0 19.2

(2) Re-analysis (3) Review

(2) 1984VIE (3) 1984GAT

(4) 4.5G2

19G8

(4) CID

(4) 1998WAL/SIE

(5) w4.3

18.1

(5) Review

(5) 1999GIL/TRA

(1) 1983TAK

(1) 7.5

31.2

(1) Ion mobility

(2) 6.0

25.0

(2) Re-analysis

(2) 1984VIE

(3) 5.7

24.0

(3) Review

(3) 1984GAT

(4) w5.96

w24.9

(4) Review

(4) 1999GIL/TRA

(1) 10.4

43.6

(1) Ion mobility

(1) 1983TAK

(2) 6.8

28.6

(2) Re-analysis

(2) 1984VIE

(continued)

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

524

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.2 (continued) BDEs of NaC–X Bonds BDEs The broken bonds (boldfaceZdissociated fragment)

NaC–Cl

(boldfaceZrecommended

Methods

data; reference in parentheses) kcal/mol

(reference in

kJ/mol

parentheses)

References

(3) 6.9

28.7

(3) Review

(3) 1984GAT

(4) w6.84

w28.6

(4) Review

(4) 1999GIL/TRA

(1) 10.1

42.5

(1) Review

(1) 1979HUB/HER

(2) 4.8G2.4

20.3G10

(2) Derived from IP

(2) 1996NIST

in ref.

NaC 2 –Cl

–ClK

NaC–Br

115.5

483.3

127.8

534.7

PI

1983PET/DAO

(1) 13.1

55.0

(1) Review

(1) 1979HUB/HER

(2) 13.9G2.5

58.1G10.6

(2) Derived from IP

(2) 1996NIST

(1) 11.5

48.2

(2) 15.5G0.7

64.8G3.0

in ref. –I

NaC–O

(1) 19.3

80.9

(1) Derived

(1) 1979HUB/HER

(2) 8.8G4.5

37G19

(2) Derived from IP in ref.

(2) 1996NIST

94.2

394.1

PI

1983PET/DAO

177.2

741.4

NaC–NaO

56.8

237.7

PI

1983PET/DAO

NaC(H2)x–H2 xZ0

2.45G0.2

10.4G0.8

Equilibrium

1994BUS/KEM

2.25G0.2

9.4G0.8

(1) 62.7

262

(1) MS

(1) 1986TSI/GUS

(2) 53.5

224

(2) Combined

(2) 2005BRE/CAH

NaC 2 –O

–OK

1

NaC(NaF)x–NaF xZ0

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

1 2 3

(1) 47

525

197

(2) 39.0

163

(2) 55.6 (2) 48.7

233 204

4

(2) 45.4

190

5

(2) 51.9

217

6

(2) 46.4

194

7

(2) 50.0

209

8

(2) 50.3

210

9

(2) 45.0

188

10

(2) 48.0

201

NaC(NaF)x–(NaF)2 xZ0

41.7

175

1

43.8

183

2

53.5

224

3

43.1

180

4

46.4

194

5 6

47.5 45.7

199 191

7

49.3

206

8

44.3

185

9

41.9

176

Combined

2005BRE/CAH

Combined

2005BRE/CAH

Combined

2005BRE/CAH

NaC(NaF)x–(NaF)3 xZ0

57.4

240

1 2

52.6 58.8

220 246

3

55.4

232

4

53.0

222

5

57.7

241

6

56.0

234

7

54.4

228

8

52.3

219

NaC(NaF)x–(NaF)4 xZ0

48.7

204

1

40.4

169

2

53.3

223

3

44.0

184

4

45.4

190

5

50.3

210

(continued)

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

526

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.2 (continued) BDEs of NaC–X Bonds BDEs The broken bonds (boldfaceZdissociated fragment)

(boldfaceZrecommended

Methods

data; reference in parentheses) kcal/mol

(reference in

kJ/mol

parentheses)

References

6

43.4

181

7

44.7

187

NaC–NaCl

42.4

177

MS

1959CHU

NaC–HCl

12.2

51.0

FA

1980PER/ROW

FA

1980PER/ROW

NaC(N2)x–N2 xZ0

8.0

33.5

1

5.3

22.2

NaC(CO)x–CO xZ0

(1) 12.9

54

(1) HP MS

(1) 1983CAS/PET

(2) 7.4G1.9

31G8

(2) GIB MS

(2) 1998WAL/SIE

(1) 7.9

33

(2) 6.0G0.7

25G3

NaC–NaOH –(NaOH)2

45.7G2.6 41.8G7.2

191G13 175G30

Derived

1985KUD/BUT

–(NaOH)3

43.7G9.6

183G40

67.6G4.3

283G18

Review

1998ELL/AHL

xZ0

(1) 13.7

57.3

(1) FA

(1) 1980PER/ROW

66.5 46.0

(2) HP MS

(2) 1984PET/MAR

1

(2) 15.9 (2) 11.0

2

(2) 9.7

40.6

3

(2) w8.4

w35

1

NaC–Na2O

NaC(CO2)x–CO2

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

527

NaC(H2O)x–CO2 xZ1 2 3

12.6

52.7

10.3 w7.2

43.1 w30

HP MS

1984PET/MAR

(1) FA

(1) 1980PER/ROW

(2) HP MS

(2) 1983CAS/PET

NaC(SO2)x–SO2 xZ0

(1) 18.9

79.1

1

(2) 16.6

69.5

2

(2) 14.3

59.8

3

(2) w12.3

w52

NaC(H2O)–SO2

16.9

70.7

HP MS

1984UPS/SCH

NaC–O3

12.5

52.3

FA

1982ROW/VIG

NaC(H2O)x–H2O xZ0

(1) 24.0

100.4

(1) HP MS

(1) 1970DZI/KEB

(2) 24.1G1.4

101G6

(2) MS

(2) 1982BUR/HAY

(3) 22.6G1.8 (4) 24.7G1.8

94.6G7.5 103.3G7.5

(3) CID (4) CID

(3) 1994DAL/TJE (4) 2002ARI/SHO

(5) CID

(5) 2004AMI/ARM

(5) 21.8G1.5

91.2G6.3

1

(1) 19.8

82.8

(3) 19.6G1.4

82.0G5.8

2

(1) 15.8

66.1

(3) 16.8G1.4

70.4G5.8

(7) 16.1

67.4

(1) 13.8 (3) 13.1G1.4

57.7 55.0G5.8

(6) 12.6G0.2

52.7G0.8

(6) HP MS

(6) 1978CAS/HOL

(7) 12.7

53.1

(7) Electron swarm

(7) 1996BLA/KLA

(1) 12.3

51.5

(8) 10.7

44.8

(8) HP MS

(8) 1976TAN/LIA

5

(1) 10.7

44.8

N

(9) w10.5

w44

(9) Extrapolate

(9) This volume

20.2

84.5

HP MS

1984UPS/SCH

Equilibrium

2004BLA/PES

3

4

NaC(SO2)–H2O

NaC(NaF)(H2O)x–H2O xZ0

17.0

71.1

1

15.9

66.6

(continued)

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

528

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.2 (continued) BDEs of NaC–X Bonds BDEs The broken bonds (boldfaceZdissociated fragment)

(boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NaC(NaCl)(H2O)x–H2O xZ0 1

18.2 16.8

76.1 70.3

2

13.4

56.1

3

12.7

53.1

xZ0

17.7

74.1

1

17.2

72.0

Equilibrium

2004BLA/PES

Equilibrium

2004BLA/PES

NaC(NaBr)(H2O)x–H2O

NaC(NaI)(H2O)x–H2O xZ0

(1) 19.3G1

80.8G4.2

(1) Equilibrium

(1) 2003ZHA/CAR

(2) 18.0

75.3

(2) Equilibrium

(2) 2004BLA/PES

1

(1) 19.2G1

80.3G4.2

(2) 17.2

72.0

2

(1) 13.4G1

56.1G4.2

(2) 14.0

58.6

3

(1) 13.6G1 (2) 13.2

56.9G4.2 55.2 49.4G4.2

4

(1) 11.8G1

5

(1) w11

w46

N

(3) w10.5

w44

(3) Extrapolate

(3) This volume

xZ0

16.7G1

69.9G4.2

Equilibrium

2003ZHA/CAR

1

17.8G1

74.5G4.2

NaC(NaI)2(H2O)x–H2O

NaC(CO2)(H2O)x–H2O xZ0

(1) 22.9

95.8

(1) FA

(1) 1980PER/ROW

(2) w20.7

w86.6

(2) HP MS

(2) 1984PET/MAR

1

(2) w17.4

w72.8

2

(2) w12.4

w51.9

17.7

74.1

Equilibrium

2004BLA/PES

15.9

66.5

NaC(NO2)(H2O)x–H2O xZ0 1

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

529

NaC(NO3)(H2O)x–H2O xZ0

17.4

72.8

1

16.1

67.4

Equilibrium

2004BLA/PES

NaC(NH3)–H2O

19.8G1.1

83.0G4.8

CID

2001AMI/ARM

(L)NaC–H2O LZCH3OH C2H5OH

19.8G1.1 18.4G1.6

83.0G4.8 77.1G6.8

CID

2001AMI/ARM

CH3OCH3

18.0G1.1

75.2G4.8

C6H6

18.2G1.4

76.2G5.8

16.0G0.3 14.9G0.3

66.9G1.3 62.3G1.3

BIRD

2003LEM/BUS

(1) CID

(2) 2005YE/MOI

(L)NaC–H2O LZAlanine ethyl ester Betaine Maiba

15.1G0.3

63.2G1.3

Sarcosinr ethyl ester

16.0G0.3

66.9G1.3

Valine

15.9G0.2

66.5G0.8

(Gly)NaC(H2O)x–H2O GlyZglycine xZ0

(1) 17.9G1.3

75.1G5.3

1

(1) 13.5G1.8

56.5G7.4

2

(1) 9.5G1.5

39.7G6.2

3 N

(1) 8.5G2.0 (2) w10.5

35.6G8.5 w44

(2) Extrapolate

(2) This volume

BIRD

2005LEM/BUS

(L)NaC–H2O LZa-methyl-proline

11.5G0.2

48G1

N-methyl-proline

11.0G0.2

46G1

Proline methyl ester

12.2G0.1

51.0G0.5

(Gln)NaC(H2O)x–H2O xZ0 1

(1) 12.4G0.2

52G1

(2) 9.6G0.5

40G2

BIRD

(1) 2005LEM/BUS(b) (2) 2006LEM/WU

GlnZglutamine

(AsnOMe)NaC–H2O xZ0 1

(1) 12.7G0.2

53G1

(2) 8.8G0.2

37G1

BIRD

(1) 2005LEM/BUS(b) (2) 2006LEM/WU

AsnZasparagine

(continued)

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

530

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.2 (continued) BDEs of NaC–X Bonds BDEs The broken bonds (boldfaceZdissociated

(boldfaceZrecommended

Methods

data; reference in parentheses)

fragment)

kcal/mol

(reference in

kJ/mol

parentheses)

References

(GlnOMe)NaC–H2O xZ0 1

(1) 11.7G0.2 (2) 9.3G0.5

49G1 39G2

BIRD

BIRD

(1) 2005LEM/BUS(b) (2) 2006LEM/WU

GlnZglutamine

(AsnOEt)NaC–H2O xZ0 1 AsnZasparagine

NaC(NH3)x–NH3 xZ0

1

(1) 12.4G0.2

52G1

(2) 9.1G0.2

38G1

(1) 29.1G0.4 (2) 28.4

121.8G1.7 118.8

(1) 2005LEM/BUS(b) (2) 2006LEM/WU

(1) Equilibrium (2) CID

(1) 1978CAS/HOL (2) 1989MAR/SQU

(3) 25.6

107.1

(3) Equilibrium

(3) 1999HOY/NOR

(4) 25.4G1.3

106.2G5.4

(4) CID

(4) 2000ARM/ROD

(5) 25.6G2.8

107.1G11.7

(5) CID

(5) 2002ARI/ROD

(1) 22.9G0.2

95.8G0.8

2

(1) 17.1G0.2

71.5G0.8

3

(1) 14.7G0.1

61.5G0.4

4 5

(1) 10.7G0.2 (1) 9.7G0.2

44.8G0.8 40.6G0.8

N

(6) w4.7

w20

(6) Extrapolate

(6) This volume

NaC–ND3

25.6G1.3

107.2G5.4

CID

2001AMI/ARM

(L)NaC–NH3 LZH2O

CID

22.8G1.1

95.5G4.8

CH3OH

22.8G1.6

95.5G6.8

C2H5OH

21.9G1.4

91.7G5.8

CH3OCH3

21.4G1.4

89.7G5.8

C6H6

21.4G1.1

89.7G4.8

NaC–ScF3

33

138

MS

1986TSI/GUS

NaC–HNO3

20.6

86.2

FA

1980PET/ROW

NaC–AlF4

119.0

497.9

Derived

1985ZHU/NIK

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

–GaF4

120.3

503.3

–ScF4

118.0

493.6

–YF4 –LaF4

119.9 125.6

501.6 525.4

7.2

30.1

NaC–CH4

HP MS

531

1983CAS/PET

NaC(CH3OH)x–CH3OH xZ0

(1) 26.6G0.2

111.3G0.8

(1) Equilibrium

(1) 1989GUO/CON

(2) 24.0G0.2

100.4G0.8

(2) Equilibrium

(2) 1999HOY/NOR

(3) 22.3G1.4 (4) 26.1G2.7

93.2G5.7 109.2G11.3

(3) CID (4) CID

(3) 1999ROD/ARM (4) 2002ARI/SHO

(5) CID

(5) 2004AMI/ARM

CID

2001AMI/ARM

(5) 23.6G1.4

98.8G5.7

1

(1) 20.2G0.2

84.5G0.8

2

(1) 17.4G0.4

72.8G1.7

3

(1) 15.7G0.2

65.7G0.8

(L)NaC–CH3OH LZH2O

22.4G1.4

93.6G5.8

NH3 C2H5OH

21.4G1.6 20.5G1.6

89.7G6.8 85.9G6.8

CH3OCH3

19.6G1.1

82.0G4.8

C6H6

20.0G1.1

83.9G4.8

NaC(CH3CN)x–CH3CN xZ0

(1) 32.5

136.0

(1) HP MS

(1) 1999HOY/NOR

(2) 30.8G1.1

128.9G4.6

(2) CID

(2) 2001VAL/AMU

(3) 30.0G2.3 (2) 25.5G1.9

125.5G9.6 106.7G8.0

(3) CID

(3) 2002ARI/ROD

1

(4) 24.4G0.3

102.1G1.3

(4) HP MS

(4) 1976DAV/KEB

2

(2) 21.1G0.7

88.2G3.0

(4) 20.6G0.5

86.2G2.1

3

(2) 14.9G0.6

62.5G2.5

(4) 14.9G0.2

62.3G0.8

4

(2) 12.0G0.9

50.4G3.7

(4) 12.7G0.2

53.1G0.8

NaC–C2H4

10.7G1.1

44.6G4.4

GIB MS

2000ARM/ROD

NaC–C2H5OH

(1) 24.7G0.9

103.3G3.7

CID

(1) 1999ROD/ARM

(continued)

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

532

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.2 (continued) BDEs of NaC–X Bonds BDEs The broken bonds (boldfaceZdissociated fragment)

(boldfaceZrecommended

Methods

data; reference in parentheses) kcal/mol

(reference in

kJ/mol

parentheses)

References

(2) 28.1G2.0

117.6G8

(2) 2002ARI/SHO

(3) 26.6G1.3

111.4G5.6

(3) 2004AMI/ARM

LZH2O

23.8G1.6

99.4G6.8

NH3

23.3G1.4

97.4G5.8

CH3OH

23.8G1.6

99.4G6.8

C6H6

23.1G1.1

96.5G4.8

(L)NaC–C2H5OH CID

2001AMI/ARM

NaC(DME)x–DME, DMEZ dimethyl ether CH3OCH3 xZ0

(1) 22.2G1.2

93G5

(2) 24.2G1.4

101.4G5.7

1

(1) 18.9G1.2

79G5

2

(1) 16.0G1.2

67G5

3

(1) 13.9G1

58G4

LZH2O

21.4G1.1

89.7G4.8

NH3

20.7G1.4

86.8G5.8

CH3OH

21.2G1.4

88.8G5.8

C6H6

20.0G1.1

83.9G4.8

NaC–CH3C(O)H

27.3G0.8

NaC–n-C3H7OH

26.1G1.0

CID

(1) 1997MOR/RAY (2) 2004AMI/ARM

(L)NaC–CH3OCH3

NaC–i-C3H7OH

CID

2001AMI/ARM

114.4G3.4

CID

2000ARM/ROD

109.3G4.1

GIB MS

1999ROD/ARM

(1) 27.3G1.0

114.4G4.3

(1) GIB MS

(1) 1999ROD/ARM

(2) 29.7

124.2

(2) HP-M

(2) 1999HOY/NOR

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

533

NaC(MeCOMe)x– (MeCOMe) xZ0

(1) 33.4G0.2 (2) 30.8

139.7G0.8 128.9

(1) Equilibrium (2) Equilibrium

(1) 1989GUO/CON (2) 1999HOY/NOR

1

(3) 31.4G1.0

131.3G4.1

(3) CID

(3) 2000ARM/ROD

(1) 25.2G0.1

105.4G0.4

CID

2002MOI/ARM

2

(1) 20.7G0.2

86.6G0.8

3

(1) 14.7G0.2

61.5G0.8

28.4G1.4

119G6

NaC–C2H5C(O)OH

NaC–CH3C(O)OCH3

NaC–n-C4H9OH –i-C4H9OH

(1) 44

184

(1) ICR

(1) 1975STA/BEA

(2) 31.8

133

(2) Kinetics

(2) 1999HOY/NOR

26.4G1.1

110.3G4.7

GIB MS

1999ROD/ARM

25.4G1.4

106.4G5.7

–s-C4H9OH

28.3G1.2

118.4G5.1

–t-C4H9OH

28.1G1.0

117.6G4.1

NaC–CH3C(O)C2H5

31.5G1.7

132G7

CID

2002MOI/ARM

(1) 1983CAS/PET

NaC(DXE)x–(DXE), DXEZCH3O(CH2)2OCH3 xZ0

1 2

(1) 47.2

197.5

(1) HP MS

(2) 38.2G0.9

159.9G3.9

(2) GIB MS

(2) 2000ARM/ROD

(3) 38.8

162.5

(3) Derived

(3) 2004TSA/SIU

(4) GIB MS

(4) 1997MOR/RAY

CID

1999MOR/RAY

(1) 35.1

146.9

(4) 27.2G1.9

114G8

(1) 23.2

97.1

60.7G3.1

254G13

71.2G4.3

298G18

71.7G4.5

300G19

NaC–L LZ(12c-4), 12c-4Z12crown-4, c-(CH2O)4 (15c-5), 15c-5Z15crown-5, c-(CH2O)5 (18c-6), 18c-6Z18crown-6, c-(CH2O)6

(continued)

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

534

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.2 (continued) BDEs of NaC–X Bonds BDEs The broken bonds (boldfaceZdissociated fragment)

(boldfaceZrecommended

Methods

data; reference in parentheses) kcal/mol

(reference in

kJ/mol

parentheses)

References

NaC(Et2CO)x–(Et2O) xZ0 1

31.0G0.3 22.9G0.3

129.7G1.3 95.8G1.3

2

16.4G0.3

68.6G1.3

NaC–CH3NH2

–C2H5NH2

NaC–n-C3H7NH2 –i-C3H7NH2

NaC–MeC(O)NH2

Equilibrium

1989GUO/CON

(1) 32.1

134.3

(1) HP MS

(1) 1989GUO/CON

(2) 26.3G0.2

110.0G0.8

(2) HP MS

(2) 1999HOY/NOR

(3) 27.0G1.4 (3) 27.7G2.3

113.0G5.9 115.9G9.6

(3) CID

(3) 2002ARI/ROD

(1) 29.6G1.4

124G6

CID

(1) 1996KLA/AND

(2) 31.4

131.4

34.7

145

–MeC(O)NHMe

35.7

149

–MeC(O)NMe2

37.5

157

NaC–H2NCH2C(O)NH2

41.4

173

–(H2NC(O)CH2)2

44.5

186

–H2NCH2C(O)

42.8

179

(1) 36.2 (2) 37.7G0.9

151.5 157.8G3.7

(2) 1999HOY/NOR

CID

1996KLA/AND

CID

1996KLA/AND

(1) Kinetics (2) CID

(1) 1999HOY/NOR (2) 2000ARM/ROD

NHCH2CO2H

NaC–(CH3)2NCHO

NaC(C6H6)x–C6H6 xZ0

1

(1) 28.0

117.2

(1) HP MS

(1) 1990GUO/PUR

(2) 28G1 (3) 22.5G1.5

117.2G4 94.3G6.1

(2) Combined (3) CID

(2) 1999RYZ/DUN (3) 2000AMI/ARM

(4) CID

(4) 2004AMI/ARM

CID

2001AMI/ARM

(4) 23.2G1.4

97.0G5.9

(3) 19.2G1.5

80.3G6.2

20.7G1.6 19.4G1.1

86.8G5.8 81.0G4.8

(L)NaC–C6H6 LZH2O NH3

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

535

CH3OH

19.4G1.1

81.0G4.8

C2H5OH

19.6G1.6

82.0G6.8

CH3OCH3

18.9G1.1

79.1G4.8

16.9G1.0 15.0G1.0

70.7G4.1 62.8G4.3

CID

2002AMU/ROD

(1) 28G3 (2) 24.0G0.8

117.2G12.6 100.3G3.4

(1) Combined (2) GIB MS

(1) 1999RYZ/DUN (2) 2000ROD/ARM(b)

(3) GIB MS

(3) 2002AMU/ROD

NaC(C6H5F)x–C6H5F xZ0 1

NaC(C6H5OH)x–C6H5OH xZ0

(3) 24.8G0.9

103.6G3.9

(3) 18.8G0.8

78.7G3.5

NaC–C6H5CN

32.7G1.4

136.8G5.9

CID

2002ARI/ROD

NaC(C6H5NH2)x–C6H5NH2 xZ0

29.0G0.8

121.2G3.4

CID

2003ARM/ROD(b)

22.9G0.7

95.9G2.8

27.2G1.1

113.8G4.6

CID

2002AMU/ROD(b)

20.0G0.7

83.6G2.8

27.4G2.1

114.5G8.7

CID

2003AMU/ROD(c)

20.6G0.7

86.2G2.8

25.8G1.3 21.0G0.7

107.9G5.3 87.7G2.9

CID

2003AMU/ROD

31.3G1.0

130.8G4.3

CID

2006CHI/CHU

34.5G1.0

144.2G4.0

1

1

NaC(C6H5CH3)x–C6H5CH3 xZ0 1

NaC(C6H5OCH3)x– C6H5OCH3 xZ0 1

NaC(C10H8)x–C10H8 xZ0 1

NaC–benzoic acid, substituted

C(O)COH

Y YZH 2-OH

(continued)

7366—CHAPTER 11—3/2/2007—13:15—SHANMUGAM—15367—XML MODEL B – pp. 493–569

536

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.2 (continued) BDEs of NaC–X Bonds BDEs (boldfaceZrecommended

The broken bonds (boldfaceZdissociated fragment)

Methods

data; reference in parentheses) kcal/mol

(reference in

kJ/mol

3-OH

31.5G0.8

131.9G3.3

4-OH 2,3-(OH)2

31.6G1.2 35.0G1.0

132.4G4.9 146.5G4.3

2,4-(OH)2

34.9G1.0

145.9G4.0

2,5-(OH)2

34.9G1.2

146.0G4.8

2,6-(OH)2

34.8G0.9

145.7G3.9

3,4-(OH)2

33.0G0.8

137.9G3.2

3,5-(OH)2

32.8G1.7

137.3G7.2

parentheses)

References

NaC–uracil, substituted

X'

O X

N 3 N1 6 5 X 0 ZH

XZH Me Me H H

O

5-Me 6-Me

Me

(1) 33.7

141

(1) VG-MS

(1) 1996CER/WES

(2) 32.4G0.8

135.7G3.4

(2) GIB MS

(2) 2005YAN/ROD

H

(2) 36.3G1.0

151.9G4.1 151G4 144.8G3.8

(3) CID

(3) 2004ROD/ARM

H

(3) 36.1G1.0 (2) 34.6G0.9 (3) 34.4G1.0

144G4

(1) 34.4

144

(2) 32.6G0.9

136.4G3.8

(2) 32.9G1.4

137.6G5.8

(3) 32.7G1.4

137G6

(2) 37.0G1.1

154.9G4.7

(3) 36.8G1.2 (2) 33.0G1.2

154G5 137.9G5.1 (4) CID

(4) 2004YAN/ROD

CID

2006YAN/ROD

H H Me

H

5,6-diMe H

(3) 32.7G1.2

137G5

H

5-F

H

(4) 35.6G1.0

149.0G4.3

H

5-Cl

H

(4) 33.8G0.8

141.4G3.4

H

6-Cl

H

(4) 33.3G1.1

139.5G4.4

H

5-Br

H

(4) 34.0G1.1

142.3G4.8

H

5-I

H

(4) 33.3G1.1

139.5G4.4

33.4G0.8

139.8G3.3

NaC–thiouracil, substituted

A NH1

NH 2 3 4 6 5

AZS A 0 ZO

A'

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BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

O

S

30.1G1.1

125.8G4.7

S

S

23.9G1.4

100.2G5.8

5-CH3

34.0G1.3

142.3G5.5

6-CH3

34.3G0.9

143.6G3.8

537

NaC–thiouracil, substituted

S NH1

NH 2 3 O 4 6 5 CH3

NaC–5-methyl-2-thiouracil

33.9G1.4

142G6

–6-methyl-2-thiouracil

34.4G1.0

144G4

(1) 41.1 (2) 33.4G1.0

172 139.6G4.2

NaC–adenine –cytosine

(1) 42.3

177

–guanine

(1) 43.5

182

NaC–1H-1,2,4-triazole

29.8G1.2

124.6G5.2

–2H-1,2,3-triazole

23.1G1.0

96.6G4.3

–2H-tetrazole

27.6G0.9

115.4G3.6

NaC–pyrrole

24.8G1.1

103.7G4.8

–1-methyl-pyrrole

27.0G0.8

113.1G3.4

–pyrazole –1-methyl-pyrazole

30.8G2.0 31.6G0.7

129.0G8.5 132.4G2.9

–imidazole

33.7G1.3

140.9G5.3

–1-methyl-imidazole

38.7G1.2

161.8G5.0

NaC–pyridine

Na+ N

CID

2006YAN/ROD

CID

2004ROD/ARM

(1) VG-MS (2) GIB MS

(1) 1996CER/WES (2) 2000ROD/ARM

CID

1999ROD/ARM

CID

2002HUA/ROD

(1) 31.7

132.6

(1) Kinetics

(1) 1999HOY/NOR

(2) 30.4G0.7

127G3

(2) CID

(2) 2000ROD/ARM(b)

(3) 30.5G0.6

127.5G2.5

(3) CID

(3) 2000AMU/ROD

CID

2001ROD

NaC–Y-pyridine

Na+

Y N

YZo-methyl

30.9G1.1

129.2G4.7

m-methyl

32.1G1.1

134.2G4.4

p-methyl

32.1G1.0

134.4G4.0

(continued)

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

538

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.2 (continued) BDEs of NaC–X Bonds BDEs (boldfaceZrecommended

The broken bonds (boldfaceZdissociated fragment)

Methods

data; reference in parentheses) kcal/mol

(reference in

kJ/mol

parentheses)

References

NaC–Y-pyridine

Na+

Y N

YZo-NH2 m-NH2

35.0G1.4 32.5G0.9

146.5G5.9 136.1G3.8

p-NH2

35.0G1.1

146.6G4.6

NaC–pyridazine –pyrimidine –pyrazine –1,3,5-triazine

(1) 38.0G0.7

159G3

(2) 38.3G0.8

160.4G3.2

(1) 24.6G1.0

103G4

(2) 24.7G0.9

103.5G3.9

(1) 25.6G1.0 (2) 25.9G0.8

107G4 108.2G3.5

(2) 21.3G0.7

89.0G3.0

(3) 21.0G0.7

88G3

CID

CID

2001ROD(b)

(1) 2000ROD/ARM(b) (2) 2000AMU/ROD

(3) 1999ROD/ARM

NaC(L)x–L, LZindole xZ0 1

(1) 34G3

142.3G12.6

(1) Combined

(1) 1999RYZ/DUN

(2) 28.9G0.7

121.1G2.9

(2) CID

(2) 2005RUA/YAN

(2) 23.3G0.7

97.4G2.9

CID

2005YE/MOI

NaC(H2O)x–Gly GlyZglycine xZ1

30.6G1.7

128.0G7.3

2

24.2G1.8

101.2G7.4

3

19.5G1.6

81.4G6.6

4

13.8G2.0

57.9G8.3

NaC–L, a-amino acids LZGly (glycine)

Ala (alanine)

(1) 38.0

159

(1) FAB

(1) 1993BOJ/BRE

(2) 39.7G1.4

166G6

(2) CID

(2) 2002MOI/ARM

(3) 38.5G1

161G4

(3) CAD

(3) 2003KIS/OHA

(4) 38.5

161

(4) FT-ICR

(4) 2003GAP/DUN

(5) 39.8G1.2

166.7G5.1

(5) CID

(5) 2005YE/MOI

(1) 39.4

165

(3) 39.9G1

167G4

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BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

(4) 40.4 Arg (arginine) Asn (asparagine)

169

(6) 38.0

159

(3) O53.8G1 (3) 49.2G1

O225G4 206G4

Asp (asparagine)

(3) 48.5G1

203G4

Cys (cysteine)

(3) 41.8G1

175G4

(4) 42.8

179

Gln (glutamine)

(3) 50.7G1

212G4

Glu (glutamic acid)

(4) 48.8G1

204G4

His (histidine)

(3) 52.3G1

219G4

Ile (isolecine)

(4) 44.2 (3) 42.1G1

185 176G4

Leu (leucine)

(3) 41.8G1

175G4

Lys (lysine)

(3) O50.9G1

O213G4

Met (methionine)

(7) 48.3G2.6

202G11

Phe (phenylalanine)

(3) 47.3G1

198G4

(4) 47.3

198

(6) 44.9

188

(8) 41.5 (9) 49.1G1.6

173.6 205.5G6.8

Pro (proline)

(3) 46.8G1

196G4

(4) 41.8

175

(5) 44.5G1.0

186G4

(10) 44.9G1.0

188G44

Ser (serine)

(3) 45.9G1

192G4

(4) 44.9

188

Thr (threonine) Trp (tryptophan)

(3) 47.1G1 (3) 50.2G1

197G4 210G4

(4) 49.0

205

(8) 43.0

179.9

Tyr (tyrosine)

Val (valine)

539

(9) 51.9G1.8

217.1G7.7

(3) 48.0G1

201G4

(8) 41.8

174.9

(9) 50.0G2.3

209.4G9.6

(1) 41.1 (3) 41.3G1

172 173G4

(4) 41.3

173

(6) Equilibrium

(6) 2001GAP/DUN

(7) CID

(7) 2004ROD/ARM

(8) Kinetics (9) CID

(8) 2000RYZ/DUN (9) 2004RUA/ROD

(10) CID

(10) 2006MOI/ARM

CID

2006MOI/ARM

NaC–Aze

42.8G1.2

179G5

–Pip AzeZazetidine-2-carboxylic

44.5G1.4

186G6

NaC–CH3Ala

(1) 42.1

176

(1) FT-ICR

(1) 2003GAP/DUN

–CH3Gly –CH3Val

(2) 39.9 (1) 42.8

167 179

(2) FAB

(2) 1993BOJ/BRE

acid PipZpipecolic acid

(continued)

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

540

Comprehensive Handbook of Chemical Bond Energies

Table 11.3.2 (continued) BDEs of NaC–X Bonds BDEs The broken bonds (boldfaceZdissociated fragment)

(boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NaC–L LZa-AB N-acetyl-Gly

(1) 39.0 (2) 44.5

163.2 186

c-GlyGly

(2) 34.2

143

c-AlaGly

(2) 35.6

149

c-AlaAla

(2) 36.1

151

GlyGly

(2) 42.3

177

(1) FAB (2) HP MS

(1) 1993BOJ/BRE (2) 1998CER/HOY

(3) 43.0

180

(3) CID

(3) 1996KLA/AND

(4) 40.8

171

(4) Kinetics

(4) 1999FEN/GRO

(5) 48.5G2 (2) 42.8

203G8 179

(5) Kinetics

(5) 2004KIS/WES

GlyAla AlaGly

(2) 42.5

178

AlaAla

(2) 43.0

180

GlyGly-OEt

(2) 43.3

181

GlyGly-NH2

(2) 43.7

183

Kinetics

1999CER/WES

Kinetics

1998CER/HOY

MALDI

1999GID/WYT

NaC–arabinose

40.6

170

–galactose –gentiobiose

42.3 48.0

177 201

–glucose

41.6

174

–lactose

48.8

204

–mannose

42.8

179

–melibiose

47.3

198

–ribose

42.1

176

–xylose

40.9

171

NaC–L, dipeptides LZcyclo-glycylglycine

34.2

143

cyclo-alanylglycine

35.6

149

cyclo-alanylalanine

36.1

151

N-acetyl glycine

41.1

172

8.1 12.9

34 54

NaC(PET)x–PET xZ0 2 4

15.8

66

6

21.0

88

PETZpoly(ethylene terephthalate) oligomer

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

541

11.3.3 NaK–X bonds Table 11.3.3 BDEs of NaL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NaK–Na

(1) 11.0 (2) 15.2G0.3

46.0 63.4G1.4

(1) Derived (2) Derived from EA in ref.

(1) 1979HUB/HER (2) 1996NIST

NaK–K

16.0G0.7

66.8G2.9

Derived from EA in ref.

1996NIST

NaK–NaH –(NaOH)2 –(NaH)3

46.6G3.8 48.0G3.3 44.7G7.2

195G16 201G14 187G30

Derived

1985KUD/BUT

ClNaK–ClNa (ClNa)7K–ClNa (ClNa)9K–ClNa

12.5G1.2 15.7G1.2 8.1G1.2

52.1G4.8 65.9G4.8 33.8G4.8

PES

1993XIA/YU

11.4

K–, KC–, and KK–X bonds

11.4.1 K–X bonds Table 11.4.1 BDEs of K–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

K–K

(1) 13.62 (2) 13.6 (3) 13.62G0.01 (4) 13.61

57.02 57 56.97G0.02 56.96

(1) Spectroscopy (2) Review (3) Spectroscopy (4) Recommended

(1) 1979HUB/HER (2) 1979MIE/GIN (3) 1991AMI (4) 1996ZHA/ZEM

Ni(100, surf.)K–K

1.5G0.3 (phys)

6.1G1.4

Scattering

1996FUH/HUL

(continued)

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

542

Comprehensive Handbook of Chemical Bond Energies

Table 11.4.1 (continued) BDEs of K–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

K–Li

19.6G1.0

K–Na

kJ/mol 82.0G4.2

Methods (reference in parentheses)

References

MS

1977ZMB/WU

(1) 15.5G1.0 64.9G4.2 (2) 15.773G0.002 65.994G0.008 (3) 15.97 66.80

Spectroscopy

(1) 1977ZMB/WU (2) 1979BRE/ENG (3) 1999ZEM/STW

K–Rb

(1) 12.4 (2) 12.1 (3) 12.838 (4) 12.840G0.001

52.0 50.5 53.716 53.723G0.005

Spectroscopy

(1) 1979HUB/HER (2) 1999KAS/FUJ (3) 2000AMI/VER (4) 2005STW

KCl(surf.)–Ag

7.1 (phys)

29.9

SEM

1976DON/ROB

KCl(surf.)–Ag

12.2

51.1

SEM

1976DON/ROB

KBr(surf.)–Ag

4.2 (phys)

17.4

SEM

1976DON/ROB

KBr(surf.)–Ag

10.6

44.4

SEM

1976DON/ROB

KCl(surf.)–Au

4.8G1.2 (phys)

20.3G4.8

SEM

1973ROB/ROB

KCl(surf.)–Au

15.2G2.3

63.7G9.6

SEM

1973ROB/ROB

KBr(surf.)–Au

8.1G1.2 (phys)

33.8G4.8

SEM

1973ROB/ROB

KBr(surf.)–Au

18.4G2.3

77.2G9.6

SEM

1973ROB/ROB

K–Zn –Cd

1.6 1.7

6.5 7.3

Spectroscopy

1984CZU/REB

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

543

K–Hg

(1) 2 (2) 2.4 (3) 2.1

8.4 9.9 8.8

(1) Review (2) Spectroscopy (3) Scattering

(1) 1974GUR/KAR (2) 1984CZU/REB (3) 1986LAC/MAI

K–Kr –Xe

1.1 1.2

4.6 5.0

Review

1979HUB/HER

K–H

(1) 43.8G1.1 (2) 43.14 (3) 41.725

183.4G4.8 180.48 174.576

Spectroscopy

(1) 1983YAN/NEL (2) 1986HUS/EFF (3) 1988ZEM/STW

K–D

43.6

182.4

Spectroscopy

1979HUB/HER

K–F

116.9

489.2

Spectroscopy

1979HUB/HER

K–Cl

103.5G2

433.0G8.4

Photofrag.

1980SU/RIL(b)

K–Br

(1) 89.9 (2) 90.6G1

376.3 379.1G4.2

Photofrag.

(1) 1979VAN/VRI (2) 1980SU/RIL

K–I

(1) 76.8 (2) 77.1G0.5

321.3 322.5G2.1

Photofrag.

(1) 1979VAN/VRI (2) 1979SU/RIL

K–O

(1) 66G3 (2) 62.6 (3) 66.4G5.0 (4) 64.9G3

276.1G12.6 261.9 277.8G21 271.5G12.6

(1) MS (2) MS (3) Review (4) Review

(1) 1977EHL (2) 1982FAR/SRI (3) 1983PED/MAR (4) 1984HYN/STE

K–O2

45

188.3

Review

1984HYN/STE

(KO)–H

(1) 124.7

521.7

(1) Derived from DfH0 in ref.

(1) 1996NIST

K–OH

(1) 85.8 (2) 84G3

359 351.5G12.6

(2) Review

(2) 1984HYN/STE

(continued)

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

544

Comprehensive Handbook of Chemical Bond Energies

Table 11.4.1 (continued) BDEs of K–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Ru(001, surf.)K–CO

18.4

77.2

TDS

1985PAO/HRB

K–KOH

19.8G4.4

83.0G18.3

PI

1990KUA/JIA

(KOH)–KOH

45.3

190

Derived from DfH0 in ref.

1996NIST

K–H2O

5.8G1.8

24.1G7.7

PI

1990KUA/JIA

K–NH3

7.6G1.8

31.8G7.7

PI

1990KUA/JIA

KF–AlF3 –GaF3 –ScF3 –YF3 –LaF3

85.8 75.7 84.4 w82.5 w72.7

359.0 316.7 353.1 w345 w304

Derived

1985ZHU/NIK

11.4.2 KC–X bonds Table 11.4.2 BDEs of KD–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) KC–K

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 20.5

85.7

(1) Spectroscopy

(1) 1979HUB/HER

(2) 19.2

80.3

(2) PI

(2) 1981LEU/HOF

(3) 19.6

81.9

(3) Derived

(3) 1996SMI/YAT

(4) Derived from IP

(4) 1996NIST

(4) 20.04G0.03 83.86G0.15

in ref.

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

545

KC(K)x–K xZ2

10.4

43.5

3 4

15.5 12.5

64.9 52.3

5

17.3

72.4

6

13.4

56.1

7

20.8

87.0

8

11.5

48.1

9

13.1

54.8

10

12.9

54.0

11 12

13.4 13.4

56.1 56.1

13

14.9

62.3

14

13.1

54.8

15

15.0

62.8

16

15.5

64.9

17

16.1

67.4

18

15.7

65.7

19 20

17.3 12.9

72.4 54.0

21

14.3

59.8

22

13.6

56.9

23

14.8

61.9

xZ2

(1) 13.8

57.9

3 4

(1) 15.9 (1) 17.8

66.6 74.3

5

(1) 19.1

80.1

6

(1) 21.7

90.7

7

(1) 20.3

84.9

8

(1) 12.7

53.1

9

(1) 14.1

58.9

10

(1) 15.7

65.6

11 12

(1) 16.4 (1) 16.4

68.5 68.5

13

(1) 16.1

67.5

14

(1) 15.7

65.6

15

(1) 19.1

80.1

16

(1) 18.9

79.1

17

(1) 17.8

74.3

18

(1) 22.6

94.6

19 20

(1) 18.2 (1) 15.2

76.2 63.7

21

(1) 15.9

66.6

22

(1) 16.4

68.5

N

(2) w19.1

w80

PD

1990BRE/CAH

(1) PD

(1) 1990BRE/CAH

(2) Extrapolate

(2) This volume

KC(K)x–K2

(continued)

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

546

Comprehensive Handbook of Chemical Bond Energies

Table 11.4.2 (continued) BDEs of KC–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) KC–Li

recommended data; reference in parentheses) kcal/mol 14.3G1.4

kJ/mol 59.9G5.9

Methods (reference in parentheses) Derived from IP

References 1996NIST

in ref.

KC–Na

(1) 14.0

58.7

(2) 14.03G0.02 58.69G0.08

(1) PI

(1) 1981LEU/HOF

(2) Derived from IP

(2) 1996NIST

in ref.

KC–He

KC–Ne

KC–Ar

KC–Kr

KC–Xe

KC–Cl

(1) 1.4

5.9

(1) Ion mobility

(1) 1983TAK

(2) 1.4

5.9

(2) Re-analysis

(2) 1984VIE

(3) 1.4 (4) 1.43

6.1 6.00

(3) Review (4) Review

(3) 1984GAT (4) 1991PET/HAM

(1) 1.8

7.7

(1) Ion mobility

(1) 1983TAK

(2) 1.8

7.7

(2) Re-analysis

(2) 1984VIE

(3) 2.0

8.3

(3) Review

(3) 1984GAT

(4) 1.86

7.79

(4) Review

(4) 1991PET/HAM

(1) 3.6 (2) 3.8

15.2 16.0

(1) Ion mobility (2) Re-analysis

(1) 1983TAK (2) 1984VIE

(3) 3.8

15.7

(3) Review

(3) 1984GAT

(4) 3.3G1.7

14G7

(4) CID

(4) 2000ROD/ARM(b)

(1) 4.6

19.2

(1) Ion mobility

(1) 1983TAK

(2) 3.8

16.0

(2) Re-analysis

(2) 1984VIE

(3) 3.8

15.8

(3) Review

(3) 1984GAT

(1) 6.2

26.0

(1) Ion mobility

(1) 1983TAK

(2) 5.7

24.0

(2) Re-analysis

(2) 1984VIE

(3) 4.7

19.5

(3) Review

(3) 1984GAT

(1) 6.4

26.9

(1) Review

(1) 1979HUB/HER

(2) 12.2G4.6

51G19

(2) Derived from IP

(2) 1996NIST

in ref.

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

–Br

547

(1) 10.1

42.3

(2) 8.5G2.5

35.7G10.5

(1) 11.0 (2) 4.2G10.6

46.2 18G45

(1) 4.2G1.2

17.5G4.8

(2) 3

13

KC–KCl

41.2

172

MS

1959CHU

KC–KBr

(1) 40.8 (2) 41.5

171 174

MS

(1) 1959CHU (2) 1973KUD/GUS

xZ0

1.45G0.2

6.1G0.8

Equilibrium

1994BUS/KEM

1

1.35G0.2

5.6G0.8

KC–CO

4.5G1.2

19G5

CID

1998WAL/SIE

KC–CO2

8.5

35.6

HP MS

1981CAS/KEE

KC–KOH

Derived

1985KUD/BUT

–I

KC–O

Derived

(1) 2003LEE/WRI (2) 2004LAV/BLA

KC(H2)x–H2

38.0G2.6

159.0G11

–(KOH)2

30.1G7.2

126G30

–(KOH)3

28.4G9.6

119G40

(1) 17.9 (2) 16.9

74.9 70.7

(1) HP MS (2) HP MS

(1) 1969SEA/KEB (2) 1976DAV/KEB

(3) 17.0

71

(3) MS

(3) 1982BUR/HAY

(4) 15.2

63.6

(4) CID

(4) 1989MAR/SQU

(5) 16G3

66.9G12.6

(5) HP MS

(5) 1990BLA/JAY(b)

1

(1) 16.1

67.4

2

(1) 13.2

55.2 (6) Electron swarm

(6) 1996BLA/MAR

(7) Extrapolate

(7) This volume

KC(H2O)x–H2O xZ0

(6) 13.0

54.4

3 4

(1) 11.8 (1) 10.7

49.4 44.8

5

(1) 10.0

41.8

N

(7) w10.5

w44

(continued)

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

548

Comprehensive Handbook of Chemical Bond Energies

Table 11.4.2 (continued) BDEs of KC–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) KC(KI)–H2O

recommended data; reference in parentheses) kcal/mol 13.1

kJ/mol

Methods (reference in parentheses)

References

54.8

Equilibrium

2004BLA/PES

HP MS

1991EVA/KEE

HP MS

1991EVA/KEE

HP MS

1981SUN/NIS

KC(CH3OH)(H2O)x–H2O xZ0

15.6G0.3

65.2G1.3

1

13.1G0.1

54.8G0.4

KC(CH3OH)x–H2O xZ2 3

KC(C6H6)x–H2O xZ1

11.3G0.2

47.3G0.8

w9.3

w39

18.1

75.7

13.7

57.3

xZ1 2

12.7 11.8

53.1 49.4

HP MS

1981SUN/NIS

KC(C6H6)2(H2O)–H2O

12.2

51.0

HP MS

1981SUN/NIS

2

KC(C6H6)(H2O)x–H2O

KC(NH3)x–NH3 xZ0

1

(1) 17.9

74.9

(1) HP MS

(1) 1976DAV/KEB

(2) 20.1

84.1

(2) HP MS

(2) 1978CAS

(3) 16.9 (4) 18.9G1.7

70.7 79G7

(3) CID (4) CID

(3) 1989MAR/SQU (4) 2003ICE/ARM

(2) 16.3

68.2

Derived

1985ZHU/NIK

(4) 16.5G1.4

69G6

2

(2) 13.5

56.5

(4) 14.1G1.2

59G5

3

(2) 11.6

48.5

(4) 11.0G1.4

46G6

4

(4) 7.4G2.6

31G11

KC–AlF4

108.3

453.3

–GaF4

105.8

442.5

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BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

549

–ScF4

109.3

457.5

–YF4

w107.6

w450

–LaF4

w107.6

w450

w16.6

w69.5

HP MS

1991EVA/KEE

xZ0

19.6G0.4

82.0G1.7

HP MS

1991EVA/KEE

1

13.5G0.3

56.5G1.3

2

12.5G0.2

52.3G0.8

KC(H2O)2–CH3OH

KC(CH3OH)x(H2O)–CH3OH

KC(CH3OH)x–CH3OH xZ0

(1) 21.9

91.6

(1) HP MS

(1) 1992EVA/KEE

(2) 19.0

79.5

(2) Derived

(2) 2003LAU/WON

(2) 20.0

83.7

1

(1) 18.0G0.5

75.3G2.1

2 3

(1) 14.5G0.4 (1) 12.5G0.2

60.7G1.7 52.3G0.8

Equilibrium

1976DAV/KEB

KC(CH3CN)x–CH3CN xZ0

24.4G0.4

102.1G1.7

1

20.6G0.5

86.2G2.1

2

18.2G0.3

76.1G1.3

3

13.6G0.4

56.9G1.7

4

11.5G0.1

48.1G0.4

38

159

MS

1973KUD/GUS

(1) 22.2 (2) 20.8

92.9 87.0

(1) Equilibrium (2) Equilibrium

(1) 1976DAV/KEB(c) (2) 1976DAV/KEB

(3) CID

(3) 1997MOR/RAY(b)

KC–K2SO4

KC(DME)x–DME DMEZdimethyl ether CH3OCH3 xZ0

(3) 17.7G1.0

74G4

1

(3) 15.5G1.0

65G4

2

(3) 12.7G1.7

53G7

3

(3) 11.0G1.9

46G8

(1) 26

109

(1) Equilibrium

(1) 1984SUN/KEB

(2) 24.4

102

(2) CID

(2) 1996KLA/AND

KC(Me2C(O))x–Me2C(O) xZ0

(continued)

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550

Comprehensive Handbook of Chemical Bond Energies

Table 11.4.2 (continued) BDEs of KC–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment)

recommended data;

Methods

reference in parentheses) kcal/mol

(reference in

kJ/mol

parentheses)

References

1

(1) 21

88

2

(1) 16

67

31.1G1.4

130G6

Combined

2004MOI/ARM

(1) 35G3

146G13

(1) Equilibrium

(1) 1984SUN/KEB

(2) 31.1

130

(2) CID

(2) 1996KLA/AND

1

(1) 29G2

121G8

2

(1) 20G1

84G4

3

(1) 16G1

67G4

4 5

(1) 15.8G1 (1) 15.5G1

66G4 65G4

Equilibrium

1976DAV/KEB

KC–CH3C(O)CH2NH2

KC(Me2SO)x–Me2SO xZ0

KC–CH3NH2

19.1

79.9

–(CH3)2NH

19.5

81.6

–(CH3)3N

20.0

83.7

KC–n-C3H7NH2

KC–H2NCH2CH2OH

(1) 21.8

91.2

(1) Equilibrium

(1) 1976DAV/KEB

(2) 19.4G1

81G4

(2) CID

(2) 2004MOI/ARM

30.8G1

129G4

CID

2004MOI/ARM

107.5G2.1

Equilibrium

1976DAV/KEB(c)

CID

2004MOI/ARM

HP MS

1976DAV/KEB

KC–[(NH2CH2)2]x(NH2CH2)2 xZ0 25.7G0.5 1

22.2G0.5

92.9G2.1

2

12.9G0.3

54.0G1.3

KC–n-C3H7OH

20.1G1

84G4

–C2H5C(O)OH

20.8G1

87G4

–CH3C(O)C2H5

22.7G1

95G4

22.3

93.3

KC–C2H5OC2H5

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

551

KC(DXE)x–(DXE) DXEZCH3O(CH2)2OCH3 xZ0

(1) 30.8G1.1 (2) 28.7G1.0

128.9G4.6 120G4

1

(2) 20.3G2.9

85G12

(1) HP MS (2) CID

(1) 1976DAV/KEB(c) (2) 1997MOR/RAY(b)

CID

1999MOR/RAY

KC–L LZ(12c-4), 12c-4: 12-crown-4, 45.7G2.9

191G12

c-(CH2O)4 49.2G3.3

206G14

56.2G3.1

235G13

(1) 31

130

(1) Equilibrium

(1) 1984SUN/KEB

(2) 29.5

123

(2) CID

(2) 1996KLA/AND

1 2

(1) 21 (1) 15

88 63

3

(1) 13

54

(15c-5), 15c-5: 15-crown-5, c-(CH2O)5 (18c-6), 18c-6: 18-crown-6, c-(CH2O)6

KC(DMF)x–(DMF) DMFZN,N-dimethylformamide Me2NC(O)H xZ0

KC(DMA)x–(DMA) DMAZN,N-dimethylacetamide Me2CHC(O)NH2 xZ0

(1) 31

130

(1) Equilibrium

(1) 1984SUN/KEB

(2) 29.7

124

(2) CID

(2) 1996KLA/AND

1

(1) 24

100

2

(1) 18

75

HP MS

1976DAV/KEB

(1) Derived

(1) 2003LAW/WON

(2) CID

(2) 1996KLA/AND

KC(NH2C2H4NH2)x– (NH2C2H4NH2) xZ0

25.7G0.5

107.5G2.1

1

22.2G0.5

92.9G2.1

2

12.9G0.5

54.0G2.1

KC–MeNHC(O)H –MeC(O)NH2 –MeC(O)NHMe

(1) 28.1

117.7

(1) 28.4

118.9

(2) 29.7 (2) 30.4

124 127

(continued)

7366—CHAPTER 11—3/2/2007—13:16—SHANMUGAM—15367—XML MODEL B – pp. 493–569

552

Comprehensive Handbook of Chemical Bond Energies

Table 11.4.2 (continued) BDEs of KC–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) –MeC(O)NMe2

recommended data;

Methods

reference in parentheses) kcal/mol

(reference in

kJ/mol

(1) 31.3

131.2

(2) 29.0

121

parentheses)

References

KC(C6H6)x–C6H6 xZ0

(1) 19.2

80.3

(1) Equilibrium

(1) 1981SUN/NIS

(2) 19G1

79.5G4

(2) Combined

(2) 1999RYZ/DUN

(3) CID

(3) 2000AMI/ARM

HP MS

1986KEE/CAS

HP MS

1986KEE/CAS

(3) 17.7G1.0

74.2G4.2

1

(1) 18.8

78.7

(3) 16.3G1.7

68.2G7.1

2 3

(1) 14.5 (1) 12.6

60.7 52.7

KC(H2O)(C6H6)x–C6H6 xZ0

16.8

70

1

14.4

60

KC(H2O)2(C6H6)x–C6H6 xZ0

13.8

58

1

12.8

54

12.6

52.7

HP MS

1981SUN/NIS

CID

2002AMU/ROD

KC(H2O)3–C6H6

KC(C6H5F)x–C6H5F xZ0

13.3G0.9

55.5G3.6

1

11.2G0.8

47.0G3.5

(1) 20G3

83.7G12.6

(1) Combined

(1) 1999RYZ/DUN

(2) 17.8G0.9

74.6G3.8

(2) CID

(2) 2002AMU/ROD

(2) 15.6G0.8

65.3G3.5

(1) 22.8

95.4

(1) HP MS

(1) 1976DAV/KEB

(2) 19.9G0.9

83.4G3.7

(2) GIB MS

(2) 2003AMU/ROD(b)

(2) 17.4G0.7

72.9G3.1

KC(C6H5OH)x–C6H5OH xZ0 1

KC(C6H5NH2)x–C6H5NH2 xZ0 1

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BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

553

KC(C6H5CH3)x–C6H5CH3 xZ0

19.3G1.3

80.8G5.3

1

17.2G1.1

72.1G4.8

CID

2002AMU/ROD(b)

19.0G0.8 15.8G0.7

79.4G3.3 66.3G2.9

CID

2003AMU/ROD(c)

CID

2003AMU/ROD

KC(C6H5OCH3)x–C6H5OCH3 xZ0 1

KC(C10H8)x–C10H8 xZ0

19.4G1.3

81.2G5.3

1

17.0G0.9

71.0G3.6

(1) 25.3

106

(1) VG-MS

(1) 1996CER/WES

(2) 22.7G0.8

95.1G3.2

(2) GIB MS

(2) 2000ROD/ARM

(1) 26.3

110

CID

1999ROD/ARM

CID

2002HUA/ROD

KC–adenine –cytosine –guanine

(1) 28.0

117

–thymine

(1) 24.4

102

(2) 24.9G0.9

104.0G3.8

KC–1H-1,2,4-triazole

20.9G1.1

87.5G4.5

–2H-1,2,3-triazole

13.3G1.3

55.6G5.5

–2H-tetrazole

21.4G1.1

89.6G4.6

KC–pyrrole

20.3G0.9

85.1G3.6

–1-methyl-pyrrole

21.3G1.5

89.1G6.3

–pyrazole –1-methyl-pyrazole

20.1G0.8 22.7G0.9

84.2G3.3 94.8G3.6

–imidazole

26.2G1.4

109.7G5.7

–1-methyl-imidazole

28.1G0.6

117.7G2.7

(1) 20.7

86.6

(1) Equilibrium

(1) 1976DAV/KEB

(2) 21.5G1.0 (3) 21.7G0.9

90G4 90.6G3.9

(2) CID (3) CID

(2) 2000ROD/ARM(b) (3) 2000AMU/ROD

23.5G0.8

98.5G3.5

CID

2001ROD

KC–pyridine

K+ N KC–Y-pyridine

K+ N YZo-methyl

Y

(continued)

7366—CHAPTER 11—3/2/2007—13:17—SHANMUGAM—15367—XML MODEL B – pp. 493–569

554

Comprehensive Handbook of Chemical Bond Energies

Table 11.4.2 (continued) BDEs of KC–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds (boldfaceZdissociated fragment)

Methods

reference in parentheses) kcal/mol

(reference in

kJ/mol

parentheses)

References

m-methyl

23.9G0.8

100.1G3.5

p-methyl

23.7G1.0

99.0G4.0

YZo-NH2

24.7G0.9

103.5G3.6

m-NH2

24.2G0.8

101.2G3.3

p-NH2

26.0G0.8

108.9G3.2

(1) 25G3

104.6G12.6

(1) Combined

(1) 1999RYZ/DUN

(2) 23.9G0.9

99.8G3.9

(2) CID

(2) 2005RUA/YAN

(2) 19.0G0.7

79.4G2.9

CID

(1) 2000ROD/ARM(b)

KC–Y-pyridine

K+

Y N CID

2001ROD(b)

KC(L)x–L, LZindole xZ0 1

KC–pyridazine –pyrimidine –pyrazine –1,3,5-triazine

(1) 31.1G0.7

130G3

(2) 31.3G0.6

130.9G2.6

(1) 16.5G1.0 (2) 16.7G1.0

69G4 69.7G4.3

(1) 16.0G1.0

67G4

(2) 16.2G0.9

67.6G3.6

(1) 13.1G0.7

55G3

(2) 13.3G0.7

55.6G3.0

(1) 24.1

101

(2) 25.1G0.7

105.0G2.8

(2) 26.7G0.6

111.6G2.7

(2) 2000AMU/ROD

KC–uracil, substituted

X'

O X XZH

N 3 N1 6 5

O

X 0 ZH

Me

H

Me

H

(3) 26.5G0.7

111G3

(2) 25.9G0.8

108.3G3.3

(3) 25.8G0.7

108G3

CID

7366—CHAPTER 11—3/2/2007—13:17—SHANMUGAM—15367—XML MODEL B – pp. 493–569

(1) 2000ROD/ARM(b) (2) 2005YAN/ROD (3) 2004ROD/ARM

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

H

5-Me

H

6-Me

Me

H

(2) 25.0G0.9

104.6G3.8

(3) 24.9G0.9

104.0G3.8

H

(2) 26.1G1.3 (3) 26.1G1.2

109.4G5.4 109G5

Me

(2) 28.6G0.8

119.7G3.3

H 5,6-diMe H

555

(3) 28.4G0.7

119G3

(2) 27.2G0.8

113.8G3.2

(3) 27.0G0.7

113G3

H

5-F

H

(4) 26.3G0.9

110.2G3.8

H

5-Cl

H

(4) 24.9G0.6

104.1G2.7

H H

6-Cl 5-Br

H H

(4) 23.4G0.5 (4) 26.2G0.5

97.8G2.2 109.8G2.3

H

5-I

H

(4) 23.4G0.5

97.8G2.2

(4) 2004YAN/ROD

KC–thiouracil, substituted

A NH1

NH 2 3 4 6 5

A'

AZS A 0 ZO

24.7G0.6

103.2G2.6

O

S

23.3G1.3

97.3G5.5

S

S

19.3G0.7

80.8G2.8

5-CH3

24.1G0.7

101.2G2.8

6-CH3

25.5G0.8

106.6G3.5

CID

2005YAN/ROD(b)

CID

2005YAN/ROD(b)

CID

2004ROD/ARM

KC–thiouracil, substituted

S NH1

NH 2 3 O 4 6 5 CH3

KC–5-methyl-2-thiouracil

24.1G0.7

101G3

–6-methyl-2-thiouracil

25.6G1.0

107G4

KC–L, a-amino acids LZGly (glycine)

(1) 30.0

126

(1) CID

(1) 1996KLA/AND

(2) 28.5

119.3

(2) Combined

(2) 2003LAU/WON

(3) 29.4G1

123G4

(3) CID

(3) 2004MOI/ARM

(4) 28.9G1.0

121G4

(4) CID

(4) 2004ROD/ARM

Ala (alanine)

(2) 29.5

123.6

Leu (leucine)

(2) 30.9

129.3

(continued)

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556

Comprehensive Handbook of Chemical Bond Energies

Table 11.4.2 (continued) BDEs of KC–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds fragment)

Methods

reference in parentheses)

(boldfaceZdissociated

kcal/mol

(reference in

kJ/mol

parentheses)

References

Ile (isoleucine)

(2) 31.0

129.9

Met (methionine) Phe (phenylalanine)

(4) 33.9G2.6 (5) 24.9G5

142G11 104.2G20.9

(5) Kinetics

(5) 2000RYZ/DUN

(6) 36.0G24.3

150.5G5.8

(6) CID

(6) 2004RUA/ROD

(4) 34.4G1.0

144G4

(7) 34.7G1.0

145G4

(7) CID

(7) 2006MOI/ARM

(5) 24.7

103.3

CID

2006MOI/ARM

MALDI

1999GID/WYT

HP MS

1976DAV/KEB

Pro (proline) Trp (tryptophan)

(6) 39.4G1.4

165.0G5.8

Tyr (tyrosine)

(5) 25.2

105.4

Val (valine)

(6) 37.1G2.1 (2) 30.6

155.3G8.7 128.0

KC–Aze

31.8G1.2

133G5

–Pip

32.5G1.2

136G5

AzeZazetidine-2-carboxylic acid PipZpipecolic acid

KC(PET)x–PET xZ0

6.2

26

2

9.8

41

4

12.9

54

6

16.5

69

22.8

95.4

PETZpoly(ethylene terephthalate) oligomer

KC–aniline

7366—CHAPTER 11—3/2/2007—13:17—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

557

11.4.3 KK–X bonds Table 11.4.3 BDEs of KL–X Bonds BDEs (boldfaceZrecommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

KK–K

13.5G0.3

56.5G1.2

Derived from EA in ref.

1996NIST

KK–KOH –(KOH)2 –(KOH)3 –(KOH)4

39.0G3.3 35.6G3.1 29.4G7.2 22.9G9.6

163G14 149G13 123G30 96G40

Derived

1985KUD/BUT

11.5

Rb–, RbC–, and RbK–X bonds

11.5.1 Rb–X bonds Table 11.5.1 BDEs of Rb–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Rb–Rb

(1) 11.7 49 (2) 11.687G0.001 48.898G0.005

(1) Review (2) Spectroscopy

(1) 1979MIE/GIN (2) 1990AMI

Rb–Na

(1) 15.269G0.006 63.887G0.024 (2) 14.4 60.2

Spectroscopy

(1) 1991WAN/KAJ (2) 2001ZEM/STW

Rb–K

(1) (2) (3) (4)

52.0 50.5 50.5 53.723G0.005

Spectroscopy

(1) (2) (3) (4)

Rb–Cs

(1) 11.85G0.01 (2) w11.0

49.57G0.01 w45.9

Spectroscopy

(1) 1988GUS/AMI (2) 1999FEL/GUT

12.4 12.1 12.1 12.840G0.001

1979HUB/HER 1999KAS/FUJ 2000AMI/VER 2005STW

(continued)

7366—CHAPTER 11—3/2/2007—13:17—SHANMUGAM—15367—XML MODEL B – pp. 493–569

558

Comprehensive Handbook of Chemical Bond Energies

Table 11.5.1 (continued) BDEs of Rb–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Rb–Au

60.9G0.8

255G3.5

MS

1981BUS/WEI

Rb–Hg

2

8.4

Review

1979HUB/HER

Rb–H

(1) 40G5 (2) 42.6G1.7 (3) 41.2

167G21 178.1G7.2 172.6

(1) Review (2) RKR (3) Review

(1) 1968GAY (2) 1983YAN/NEL (3) 1991STW/ZEM

Rb–F

118G5

494G21

Review

1970DAR

Rb–Cl

(1) 107G5 (2) 102.2G2

448G21 427.6G8.4

(1) Review (2) Photofrag.

(1) 1970DAR (2) 1980SU/RIL(b)

Rb–Br

(1) 92G6 (2) 91.0G1

385G25 380.7G4.2

(1) Review (2) Photofrag.

(1) 1970DAR (2) 1980SU/RIL

Rb–I

(1) 80G3 (2) 76.2G0.5

335G13 318.8G2.1

(1) Review (2) Photofrag.

(1) 1970DAR (2) 1979SU/RIL

Rb–O

(1) 68G3 (2) 71G10 (3) 66G3

284.5G12.6 297G42 276G12.6

(1) CL (2) Review (3) Review

(1) 1970HER/HER (2) 1983PED/MAR (3) 1984HYN/STE

Rb–O2

46

192.5

Review

1984HYN/STE

Rb–OH

(1) 86.5G3 (2) 82.6G2.3 (3) 85.1G1.0

361.9G12.6 345.4G9.6 356.2G4.2

(1) Review (2) Derived (3) Derived from DfH0 in ref.

(1) 1984HYN/STE (2) 1985BAU/LAU (3) 1997GUR/BER

7366—CHAPTER 11—3/2/2007—13:17—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

RbF–AlF3 –GaF3 –ScF3 –YF3 –LaF3

86.1 75.7 86.3 w83.4 w73.6

360.2 316.7 361.0 w349 w308

Derived

559

1985ZHU/NIK

11.5.2 RbC–X bonds Table 11.5.2 BDEs of RbD–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

RbC–Rb

(1) 17.5 (2) 18.2 (3) 18.1G2.3

73.2 76.1 75.6G9.6

–Na

(3) 12.0G0.9

50.1G3.9

RbC–Ne

(1) 1.7 (2) 1.7 (3) 1.66

RbC–Ar

(1) (2) (1) (2) (1) (2)

–Kr –Xe

RbC–Cl

–Br –I

RbC–O

Methods (reference in parentheses)

References

(1) Spectroscopy (2) Derived (3) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996SMI/YAT (3) 1996NIST

7.0 7.0 6.95

(1) Ion mobility (2) Re-analysis (3) Review

(1) 1983TAK (2) 1984VIE (3) 1991PET/HAM

15.6 12.0 17.7 14.9 18.9 21.5

(1) Ion mobility (2) Re-analysis

(1) 1983TAK (2) 1984VIE

(1) 6.0 (2) 2.5G2.5

25.1 10.5G10.5

(1) Derived (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

(1) (2) (1) (2)

31.8 17.6G5.1 34.7 27G42

Derived

2004LAV/BLA

7

3.7 2.9 4.2 3.6 4.5 5.1

7.6 4.2G1.2 8.3 6.5G10

29

(continued)

7366—CHAPTER 11—3/2/2007—13:17—SHANMUGAM—15367—XML MODEL B – pp. 493–569

560

Comprehensive Handbook of Chemical Bond Energies

Table 11.5.2 (continued) BDEs of RbC–X Bonds

The broken bonds (boldfaceZ dissociated fragment) RbC–RbOH –(RbOH)2 –(RbOH)3

RbC(H2O)x–H2O xZ0

1 2 3 4 N

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

33.5G4.1 26.5G7.2 23.9G9.6

140G17 111G30 100G40

Derived

1985KUD/BUT

(1) (2) (3) (1) (3) (1) (3) (1) (1) (4)

66.5 67 66.9G12.6 56.9 58.6G12.6 51.0 54.4G12.6 46.9 43.9 w44

(1) HP MS (2) MS (3) HP MS

(1) 1970DZI/KEB (2) 1982BUR/HAY (3) 1990BLA/JAY

(4) Extrapolate

(4) This volume

15.9 16.0 16G3 13.6 14G3 12.2 13G3 11.2 10.5 w10.5

RbC(RI)–H2O

12.2

51.0

Equilibrium

2004BLA/PES

RbC(NH3)x–NH3 xZ0 1 2 3 4

18.7 15.2 13.1 11.4 10.2

78.2 63.6 54.8 47.7 42.7

Equilibrium

1978CAS

RbC–AlF4 –GaF4 –ScF4 –YF4 –LaF4

104.1 101.2 106.7 w104 w104

435.6 423.6 446.6 w435 w435

Derived

1985ZHU/NIK

86.6G1.3 74.1G0.8 65.7G0.8

Equilibrium

1976DAV/KEB

RbC(CH3CN)x–CH3CN xZ0 20.7G0.3 1 17.7G0.2 2 15.7G0.2

7366—CHAPTER 11—3/2/2007—13:17—SHANMUGAM—15367—XML MODEL B – pp. 493–569

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

3 4

561

12.5G0.2 11.1G0.6

52.3G0.8 46.4G2.5

RbC(DME)x–DME DMEZdimethyl ether CH3OCH3 xZ0 1 2 3

(1) (1) (1) (2)

64G9 51G5 33G11 38.6

(1) CID

(1) 1997MOR/RAY(c)

(2) Est. by exp.

(2) 2001SCH(b)

RbC(DXE)x–(DXE) DXEZCH3O(CH2)2 OCH3 xZ0 1

22.7G2.2 11.0G2.9

95G9 46G12

CID

1997MOR/RAY(c)

22.7G3.1

95G13

CID

1999MOR/RAY

27.7G1.4

116G6

45.9G3.1

192G13

RbC(C6H6)x–C6H6 xZ0 1

16.4G1.0 15.1G1.9

68.8G4.0 63.3G8.0

CID

2000AMI/ARM

RbC(C6H5F)x–C6H5F xZ0 1

12.9G1.3 10.4G1.2

53.9G5.5 43.6G4.9

CID

2002AMU/ROD

RbC(C10H8)x–C10H8 xZ0 1

17.6G1.2 15.8G1.0

73.5G5.1 65.9G4.1

CID

2003AMU/ROD

RbC–L LZ(12c-4), 12c-4: 12-crown-4, c-(CH2O)4 (15c-5), 15c-5: 15-crown-5, c-(CH2O)5 (18c-6), 18c-6: 18-crown-6, c-(CH2O)6

15.3G2.2 12.2G1.2 7.9G2.6 9.2

(continued)

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562

Comprehensive Handbook of Chemical Bond Energies

Table 11.5.2 (continued) BDEs of RbC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

RbC(C6H5OH)x– C6H5OH xZ0 1

16.8G0.9 14.5G0.9

70.2G3.7 60.6G3.6

CID

2002AMU/ROD

RbC(C6H5NH2)x– C6H5NH2 xZ0 1

18.4G1.1 16.3G0.7

76.9G4.8 68.4G2.9

CID

2003AMU/ROD(b)

RbC(C6H5CH3)x– C6H5CH3 xZ0 1

17.3G1.1 15.3G1.1

72.2G4.6 64.1G4.4

CID

2002AMU/ROD(b)

RbC(L)x–L, LZPhOCH3 xZ0 1

17.4G1.1 14.3G0.8

72.6G4.4 59.9G3.5

CID

2003AMU/ROD(c)

RbC(L)x–L, LZindole xZ0 21.5G0.7 1 17.5G0.7

90.1G2.9 73.3G2.9

CID

2005RUA/YAN

11.5.3 RbK–X bonds Table 11.5.3 BDEs of RbL–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

RbK–Rb

(1) 12.4 (2) 12.0G0.3

52.0 50.1G1.4

–Cs

(2) 11.7G0.5

48.8G1.9

Methods (reference in parentheses) (1) Review (2) Derived from EA in ref.

7366—CHAPTER 11—3/2/2007—13:17—SHANMUGAM—15367—XML MODEL B – pp. 493–569

References (1) 1996SMI/YAT (2) 1996NIST

BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

RbK–RbOH –(RbOH)2 –(RbOH)3 –(RbOH)4

11.6

33.2G4.5 29.9G4.3 24.4G7.2 17.2G9.6

139G19 125G18 102G30 72G40

Derived

563

1985KUD/BUT

Cs–, CsC–, and CsK–X bonds

11.6.1 Cs–X bonds Table 11.6.1 BDEs of Cs–X Bonds BDEs (boldfaceZrecommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Cs–Cs

(1) 10.0 42 (2) 10.497G0.002 43.919G0.010 (3) 10.90G0.42 45.59G1.80

(1) Review (2) Spectroscopy (3) Pyrolysis

(1) 1979MIE/GIN (2) 1985WEI/DIE (3) 1998SAR/SAR

Cs–Na

15.1G0.3

63.2G1.3

Spectroscopy

1984DIE/WEI

Cs–Rb

(1) 11.85G0.001 (2) w11.0

49.57G0.01 w45.9

Spectroscopy

(1) 1988GUS/AMI (2) 1999FEL/GUT

Cs–Au

60.4G0.8

253G3.5

MS

1981BUS/WEI

Cs–Hg

2

8

Derived

1973LIZ/SPA

Cs–H

(1) 41.95G0.09 (2) 41.913

175.50G0.34 175.364

Spectroscopy

(1) 1982YAN (2) 1988ZEM/STW

Cs–F

(1) 121.5G1.4 (2) 123.6G1.8

508.5G5.8 517.1G7.7

(1) PIMS (2) CID

(1) 1971BER (2) 1984PAR/WEX

Cs–Cl

(1) 105.6G1.6 (2) 106.5G1.8 (3) 105.3G2

441.9G6.7 445.7G7.7 440.6G8.4

(1) PIMS (2) CID (3) Photofrag.

(1) 1971BER (2) 1984PAR/WEX (3) 1980SU/RIL(b)

(continued)

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564

Comprehensive Handbook of Chemical Bond Energies

Table 11.6.1 (continued) BDEs of Cs–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Cs–Br

(1) 96.2G1 (2) 93.1G1.8 (3) 93.0G1

402.3G4.2 389.5G7.7 389.1G4.2

(1) PIMS (2) CID (3) Photofrag.

(1) 1971BER (2) 1984PAR/WEX (3) 1980SU/RIL

Cs–I

(1) 82.3G1 (2) 80.9G3.5 (3) 80.9G0.5

344.4G4.2 338.5G14.5 338.5G2.1

(1) PIMS (2) CID (3) Photofrag.

(1) 1971BER (2) 1984PAR/WEX (3) 1979SU/RIL

Cs–O

(1) 70G3 (2) 71G15 (3) 70G6

293G12.6 297G63 293G25

(1) CL (2) Review (3) Review

(1) 1970HER/HER (2) 1983PED/MAR (3) 1984HYN/STE

Cs–O2

48

200.8

Review

1984HYN/STE

(CsO)–H

129.1

540.2

Derived from DfH0 in ref.

1996NIST

Cs–OH

89.2

373

CsF–AlF3 –GaF3 –ScF3 –YF3 –LaF3

84.4 75.7 w81.3 w81.3 w71.5

353.3 316.7 w340 w340 w299

Derived

1985ZHU/NIK

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BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

565

11.6.2 CsC–X bonds Table 11.6.2 BDEs of CsD–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

CsC–Cs

(1) 12G2 (2) 15.0G2.3

50.2G8 62.6G9.6

–Na –Rb

(2) 11.5G1.0 (2) 16.3G2.4

48.1G4.2 68.3G10

CsC–Au

K1.5G6.9

CsC–He –Ne

CsC–Ar

–Kr

–Xe

CsC–F –Cl –Br –I

CsC–O

Methods (reference in parentheses)

References

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

K6G29

Derived from IP in ref.

1996NIST

(1) 1.2 (1) 1.5 (2) 1.46

5.1 6.4 6.11

Review

(1) 1984GAT

(1) (2) (3) (1) (2) (3) (1) (2) (3)

13.3 9.8 8.2 16.6 13.5 15.1 18.6 15.2 14.7

(1) Ion mobility (2) Review (3) Re-analysis

(1) 1983TAK (2) 1984GAT (3) 1984VIE

(1) 10.5G2.4

43.7G10

(1) Derived from IP in ref.

(1) 1996NIST

(1) (1) (2) (1)

107.1G10 60.5G10 32.8 29.3G10

(2) PI

(2) 1979HUB/HER

Derived

2004LAV/BLA

14

3.2 2.3 1.96 4.0 3.2 3.6 4.4 3.6 3.5

25.6G2.4 14.5G2.4 7.8 7.0G2.4

59

(2) 1991PET/HAM

(continued)

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566

Comprehensive Handbook of Chemical Bond Energies

Table 11.6.2 (continued) BDEs of CsC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) CsC–CsOH –(CsOH)2 –(CsOH)3

CsC(H2O)x–H2O xZ0 1 2 3 N

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

28.0G3.1 19.6G7.2 15.5G9.6

117G13 82G30 65G40

Derived

1985KUD/BUT

(1) (2) (1) (2) (1) (2) (1) (3)

57.3 49.7 52.3 47.4 46.9 40.8 44.4 w44

(1) HP MS (2) Diffusion tube

(1) 1970DZI/KEB (2) 1972MCM/SAW

(3) Extrapolate

(3) This volume

13.7 11.9 12.5 11.3 11.2 9.7 10.6 w10.5

CsC(CsI)–H2O

11.3

47.3

Equilibrium

2004BLA/PES

CsC–CO2 –SO2

6.2 10.8

25.9 45.2

Diffusion tube

1972MCK/SAW

CsC–AlF4 –GaF4 –ScF4 –YF4 –LaF4

102.3 101.1 w101.6 w101.6 w101.6

427.9 422.8 w425 w425 w425

Derived

1985ZHU/NIK

CsC(CH3CN)x–CH3CN xZ0 1 2 3 4

19.2G0.1 16.7G0.3 14.3G0.1 12.1G0.1 10.9G0.3

80.3G0.4 69.9G1.3 59.9G0.4 50.6G0.4 45.6G1.3

Equilibrium

1976DAV/KEB

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BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

CsC(DME)x–DME DMEZdimethyl ether CH3OCH3 xZ0 1 2 3

(1) (1) (1) (2)

13.6G1.2 10.3G1.4 8.6G2.2 8.5

(1) CID

(1) 1997MOR/RAY(c)

(2) Est. by exp.

(2) 2001SCH(b)

57G5 50G7

CID

1997MOR/RAY(c)

20.6G2.2

86G9

CID

1999MOR/RAY

24.1G1.4

101G6

40.6G2.2

170G9

CsC(C6H6)x–C6H6 xZ0 1

15.5G1.2 14.2G1.9

64.7G4.9 59.3G8.0

CID

2000AMI/ARM

CsC(C6H5F)x–C6H5F xZ0 1

12.1G1.3 9.8G1.1

50.5G5.3 40.9G4.4

CID

2002AMU/ROD

CsC(C6H5OH)x–C6H5OH xZ0 15.8G0.9 1 13.7G0.9

66.2G3.7 57.5G3.6

CID

2002AMU/ROD

CsC(C6H5NH2)x–C6H5NH2 xZ0 16.9G1.1 1 15.0G0.8

70.8G4.5 62.7G3.5

CID

2003AMU/ROD(b)

CsC(DXE)x–(DXE) DXEZCH3O(CH2)2OCH3 xZ0 13.6G1.2 1 12.0G1.7

CsC–L LZ(12c-4), 12c-4: 12-crown-4, c-(CH2O)4 (15c-5), 15c-5: 15-crown-5, c-(CH2O)5 (18c-6), 18c-6: 18-crown-6, c-(CH2O)6

57G5 43G6 36G9 35.7

567

(continued)

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568

Comprehensive Handbook of Chemical Bond Energies

Table 11.6.2 (continued) BDEs of CsC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CsC(C6H5CH3)x–C6H5CH3 xZ0 15.5G1.1 1 14.0G1.0

64.9G4.7 58.6G4.2

CID

2002AMU/ROD(b)

CsC(C6H5OCH3)x–C6H5OCH3 xZ0 15.9G1.4 1 13.8G1.0

66.6G5.6 57.9G4.0

CID

2003AMU/ROD(c)

CsC(C10H8)x–C10H8 xZ0 1

16.6G1.4 14.7G0.8

69.6G5.6 61.4G3.5

CID

2003AMU/ROD

CsC(L)x–L, LZindole xZ0 1

19.7G0.7 16.4G0.7

82.3G2.9 68.5G2.9

CID

2005RUA/YAN

21 32 41 57

MALDI

1999GID/WYT

CsC(PET)x–PET xZ0 5.0 2 7.6 4 9.8 6 13.6 PETZpoly(ethylene terephthalate) oligomer

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BDEs of H(HG)–, Li(LiG)–, Na(NaG)–, K(KG)–, Rb(RbG)–, and Cs(CsG)–X Bonds

569

11.6.3 CsK–X bonds Table 11.6.3 BDEs of CsL–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

CsK–Cs

10.4G0.4

43.7G1.5

–Rb

12.0G0.5

50.2G1.9

28.4G3.8 24.6G3.3 18.4G7.2 13.4G9.6

119G16 103G14 77G30 56G40

CsK–CsOH –(CsOH)2 –(CsOH)3 –(CsOH)4

Methods (reference in parentheses)

References

Derived from EA in ref.

1996NIST

Derived

1985KUD/BUT

7366—CHAPTER 11—3/2/2007—13:17—SHANMUGAM—15367—XML MODEL B – pp. 493–569

chapter twelve

BDEs of Be(BeC )–, Mg(MgC )–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X bonds 12.1 Be– and BeC–X bonds 12.1.1 Be–X bonds Table 12.1.1 BDEs of Be–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Be–Be

(1) 14.1 (2) 3.1

59 13.2

(1) Spectroscopy (2) Review

(1) 1984BON (2) 1996SMI/YAT

Cl2Be–BeCl2

6.8

28.5

Derived from DfH0 in ref.

1998CHA

Be–Au

(1) 68G2 (2) 73 (3) 56.8G1.0

285G8 305 237.7G4.0

(1) Review (2) Review (3) MS

(1) 1968GAY (2) 1973LIT/SPA (3) 2004BAL/CIO

(1) 47.8G0.3 (2) 52.8

199.9G1.3 221

(1) Spectroscopy (2) Derived from DfH0 in ref.

(1) 1979HUB/HER (2) 1996NIST

Be(H)x–H xZ0

(continued)

571

7366—CHAPTER 12—3/2/2007—15:02—CRCPAG—15368—XML MODEL B – pp. 571–599

572

Comprehensive Handbook of Chemical Bond Energies

Table 12.1.1 (continued) BDEs of Be–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

1 Be–D Be–T

(2) 98.9 (1) 48.5 (1) 48.9

414 203.1 204.4

Be(F)x–F xZ0 1

137.0 168.6

573 705

Derived from DfH0 in ref.

1996NIST

Be(Cl)–F

170.5

713

Derived from DfH0 in ref.

1996NIST

(1) 91.9 (2) 104 (1) 127.5

384 434 533.5

(1) MS (2) Spectroscopy

(1) 1969HIL/THE (2) 1982RAJ/PRA

Be(F)–Cl

125.4

525

Derived from DfH0 in ref.

1996NIST

Be(Br)x–Br xZ0 1

75.5 110.2

316 461

Derived from DfH0 in ref.

1996NIST

Be(I)x–I xZ0 1

62.3 81.5

261 341

Derived from DfH0 in ref.

1996NIST

(1) 118.8G1.2 (2) 103.9G3.2

496.9G4.8 434.7G13.4

(1) Spectroscopy (2) Review

(1) 1978MUR/PRA (2) 1983PED/MAR

Be(Cl)x–Cl xZ0 1

Be–O

7366—CHAPTER 12—3/2/2007—15:03—CRCPAG—15368—XML MODEL B – pp. 571–599

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

573

(3) 104.4

437

(3) Derived from DfH0 in ref.

(3) 1996NIST

Be–OBe (BeO)–H

125.0 112.1

523 469

Derived from DfH0 in ref.

1996NIST

Be(OH)x–OH xZ0

113.7

476 599

Derived from DfH0 in ref.

1996NIST

143.2

Be–S

89G14

372G59

Review

1968GAY

(BeO)–BeO

159G10

665G42

Review

1967DRO/GOL

1

12.1.2 BeC–X bonds Table 12.1.2 BDEs of BeD–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

BeC–Be

44.7

187.0

Derived

1996SMI/YAT

BeC–Au

98G7

410G29

Derived from IP in ref.

2004BAL/CIO

BeC–Ar

11.7G0.6

49.0G2.4

Spectroscopy

1976SUB/COX

BeC–H

73.4G1.2

307.3G5.0

Derived from IP in ref.

1996NIST (continued)

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574

Comprehensive Handbook of Chemical Bond Energies

Table 12.1.2 (continued) BDEs of BeC–X Bonds

The broken bonds (boldfaceZ dissociated fragment) BeC–F

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

(1) 140G10 586G42 (2) 137.5G23.4 575G98

References

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

–Cl

(2) 99.6G12

417G50

BeC–O

(1) 88G10 (2) 86.5G1.5

368G42 362.0G6.2

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

RBeC–R RZCH3 C2H5 n-C3H7 i-C3H7 t-C4H9

46.1G3.2 47.3G3.2 48.7G3.2 42.7G3.2 29.1G3.2

192.9G13.4 197.9G13.4 203.8G13.4 178.7G13.4 121.8G13.4

Review

1973LIT/SPA

BeK–Be

65.5

273.9

Derived

1996SMI/YAT

12.2 MgK and MgC–X bonds 12.2.1 Mg–X bonds Table 12.2.1 BDEs of Mg–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Mg–Mg

(1) (2) (3) (4)

2.043G0.002 2.2 2.7 2.1

C10H22Mg –MgC10H22

33.9G1.3

kJ/mol

Methods (reference in parentheses)

8.546G0.008 9 11.3 8.8

(1) (2) (3) (4)

Review Review EI Review

141.8G5.4

MS

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

References (1) (2) (3) (4)

1974GUR/KAR 1979MIE/GIN 1983WU/IHL 1996SMI/YAT

1983AKK/SCH

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

575

Mg–Li

16.1G1.5

67.4G6.3

MS

1980WU/IHL

MgO(100, surf.) –Na

1.2G0.6 (phys)

4.8G2.4

AES

1975JAN

57.4G0.7 42.1G0.7

240G3 176G3

Calorimetry

2002CAM/STA

–Ag

Mg–Au

42.8G0.6

179.1G2.7

MS

2003BAL/CIC

MgO(100, surf.) –Pd

4.6 (phys)

19.3

AFM

2000HAA/MEN

MgO(100, surf.) –Pb

(1) w27.7 (2) w24 (3) 24.6G0.5

w116 w100 103G2

(1) VTAFM (2) Calorimetry (3) Calorimetry

(1) 2000HAA/MEN (2) 2001STA/CAM (3) 2002CAM/STA

MgO(100, surf.) –He

(1) 0.2 (2) 0.29

0.7 1.21

(1) Review (2) HAS

(1) 1991VID/IHM (2) 2001BEN/BRU

Mg–Ne

w1.0

w4.1

Review

1999GIL/TRA

Mg–Ar

(1) 1.3 (2) w0.9

5.6 w3.7

(1) PI (2) Review

(1) 1996MAS/BRE (2) 1999GIL/TRA

MgO(100, surf.) –Ar

(1) 2.3 (2) 1.7 (3) 2.0

9.6 7.0 8.5

(1) LEED (2) Review (3) TPD

(1) 1988MEI/SUZ (2) 1991VID/IHM (3) 2002DOH/SCO

Mg–Kr

1.60G0.23

6.71G0.96

Spectroscopy

1997KAU/BRE(c)

MgO(100, surf.) –Cu

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 12.2.1 (continued) BDEs of Mg–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

MgO(100, surf.) –Kr

(1) 3.05 (2) 2.2

12.8 9.1

(1) LEED (2) Review

(1) 1988MEI/SUZ (2) 1991VID/IHM

Mg–Xe

2.32G0.43

9.70G1.79

Spectroscopy

1997KAU/LEU

MgO(100, surf.) –Xe

(1) 3.8 (2) 2.8

15.9 11.7

(1) LEED (2) Review

(1) 1988MEI/SUZ (2) 1991VID/IHM

Mg–H

(1) 31.6G1.4 (2) 30.2G0.7

132.0G5.8 126.4G2.9

Spectroscopy

(1) 1976BAL/CAR (2) 1978BAL/LIN

Mg–D

(1) 32.3 (2) 38.56G0.08

135.1 161.33G0.32

Spectroscopy

(1) 1979HUB/HER (2) 2000RAJ/RAJ

(InP)Mg–H

32.3G1.8

135.1G7.7

SIMS

1993BAL/KUM

(1) 110.4G1.2 (2) 106.5 (3) 110.7

461.9G5.0 445.6 463

(1) 1968HIL (2) 1979ENG (3) 1996NIST

(3) 136.1

569

(1) MS (2) CL (3) Derived from DfH0 in ref.

(1) 77.4G0.5 (2) 74.6

323.8G2.1 312

(1) 1976FAR/SRI (2) 1996NIST

(2) 112.4

470

(1) MS (2) Derived from DfH0 in ref.

(1) 78.2

327.2

(1) Spectroscopy

(1) 1979HUB/HER

Mg(F)x–F xZ0

1

Mg(Cl)x(Cl xZ0

1

Mg(Br)x–Br xZ0

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BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds (2) 70.3

294

(3) 75.99 (2) 90.7

317.96 379

54.8 69.7

Mg–O

(1) (2) (3) (4)

Mg–S

(MgO)–H

577

(2) Derived from DfH0 in ref. (3) Spectroscopy

(2) 1996NIST

229 292

Derived from DfH0 in ref.

1996NIST

327G45 363G13 251G21 358.2G7.2

(1) Spectroscopy (2) Review (3) Derived (4) Spectroscopy

(1) (2) (3) (4)

56

234

MS

1964COL/GOL

105.4

441

Derived from DfH0 in ref.

1996NIST

(1) 67G6 (2) 83.5

280G25 349

(1) 1989OPE/TEW (2) 1996NIST

(2) 106.3

445

(1) Derived (2) Derived from DfH0 in ref.

MgO(powder, surf.)–O2

2.3

9.6

IR

1978FUR/FUJ

MgO(powder, surf.)–CO

3.8

15.9

IR

1978FUR/FUJ

MgO(100, surf.) –CO

(1) (2) (3) (4) (5)

12.5 13.5 13.5 12.5 w25

(1) (2) (3) (4) (5)

1

Mg(I)x–I xZ0 1

Mg(OH)x–OH xZ0

1

78.2G9.2 86.8G3.0 60G5 85.6G1.7

3.0 (phys) 3.2 3.2 3.0 w6.0

TDS TDS TDS FT IR TPD/RAIR

(3) 2000HIR/PIN

(1) (2) (3) (4) (5)

1978MUR/BAG 1983PED/MAR 1989OPE/TEW 2000RED/AHA

1999WIC/ROD(b) 2000FRE 2001ROD/JIR 2004SPO/GRI 2005STE/RIS (continued)

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578

Comprehensive Handbook of Chemical Bond Energies

Table 12.2.1 (continued) BDEs of Mg–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

MgO(100, surf.) –CO

(1) 11.5G1.2 (2) 9.9 (3) 17G2

48.2G4.8 41.4 71G8

(1) Mol. beam (2) IRAS (3) ED

(1) 1991HEN/CHA (2) 1992HE/EST (3) 2001DOH/KIM

MgO(100, surf.)/Pd–CO

16.1G2.3

67.5G9.6

TDS

2001ABB/RIE

MgO(powder, surf.)–N2

2.6

10.9

IR

1978FUR/FUJ

MgO(powder, surf.)–NO

5.6 (phys)

23.4

IR

1978FUR/FUJ

MgO(100, surf.) –NO

5.1 (phys)

21.2

TDS

1999WIC/ROD(b)

MgO(100, surf.) –H2O

12.2

51.1

HAS

1997FER/GLE

MgO(100, surf.) –NH3

13.4

56.1

LITD

1991ART/MEI

MgO(100, surf.) –CH4

(1) (2) (3) (4)

13.0 14.0G1.0 13 11.1

(1) (2) (3) (4)

(1) (2) (3) (4)

21.3 28.0

TPD

MgO(100, surf.) –C2H6 –C3H8

5.1 6.7

3.1 3.3G0.2 3.1 2.7

ND HAS TPD TPD

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1985COU/MAD 1999PIC/GIR 2002DOH/SCO 2005TAI/DOH(b)

2005TAI/DOH(b)

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds MgO(100, surf.) –C4H10

579

8.2

34.5

TPD

2005TAI/DOH

MgO(100, surf.) –C6H14 –C8H18 –C10H22

11.0 15.0 18.5

46.0 62.9 77.6

TPD

2005TAI/DOH(b)

BrMg–CH3 –CH2CH3 –n-C3H7 –i-C3H7 –n-C4H9 –s-C4H9 –i-C4H9 –t-C4H9 –n-C5H11 –s-C5H11 –neo-C5H11 –n-C6H13 –n-C7H15 –n-C8H17 –n-C9H19 –cyclo-C3H5 –cyclo-C4H7 –cyclo-C5H9 –cyclo-C6H11 –cyclo-C7H13 –cyclo-C8H15 –CHCH2 –CH2CHCH2 –CH2C6H5 –C6H5 –C(C6H5)3

60.5 49.0 50.0 44.0 50.9 44.5 50.9 41.6 50.0 44.7 54.0 50.0 50.0 50.0 49.0 55.9 49.0 48.0 45.4 45.9 47.1 68.6 48.0 48.0 69.1 43.0

253 205 209 184 213 186 213 174 209 187 226 209 209 209 205 234 205 201 190 192 197 287 201 201 289 180

Derived

1981HOL

12.2.2 MgC–X bonds Table 12.2.2 BDEs of MgD–X Bonds

The broken bonds (boldfaceZ dissociated fragment) MgC–Mg

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) 29G1 (2) 30

kJ/mol 122G4 125

Methods (reference in parentheses) (1) PD (2) Derived

References (1) 1993DIN/KLE (2) 1996SMI/YAT

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 12.2.2 (continued) BDEs of MgC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

MgC–Fe

%44G3

%184G13

FT-MS

1991ROT/FRE

MgC–Au

64G7

268G29

Derived from IP in ref.

2004BAL/CIO

MgC–Ne

1.2G0.1

4.9G0.6

PI

1999RED/DUN(b)

MgC–Ar

(1) 4.3 (2) 3.4 (3) 4.4G0. (4) 4.59 (5) 2.7G1.7

17.9 14.2 14.6G0.5 19.20 11.3G6.8

(1) PD (2) Review (3) R2PI (4) Review (5) CID

(1) 1994PIL/YEH (2) 1995ROB/BRO (3) 1997KAU/BRE (4) 1997DUN (5) 2000AND/MUN

MgC–Kr

(1) 6.1 (2) 5.2 (3) 6.3G0.2 (4) 6.07

25.6 21.8 26.3G1.0 25.39

(1) PD (2) Review (3) R2PI (4) Review

(1) 1994PIL/YEH (2) 1995ROB/BRO (3) 1997KAU/BRE (4) 1997DUN

MgC–Xe

(1) 12.6 (2) 11.7 (3) 9.0G0.4 (4) 12.84 (5) 8.3G2.8

52.6 49.0 37.8G1.8 53.74 34.7G11.6

(1) PD (2) Review (3) R2PI (4) Review (5) CID

(1) 1994PIL/YEH (2) 1995ROB/BRO (3) 1997KAU/BRE (4) 1997DUN (5) 2000AND/MUN

MgC–H

(1) 48.9 (2) 45.6G1.4

204.6 190.8G5.8

(1) Spectroscopy (2) Ion reactions

(1) 1979HUB/HER (2) 1993DAL/CRE

MgC–D

48.7G0.2

203.6G0.8

Spectroscopy

2000RAJ/RAJ

MgC–F

(1) 106G10 (2) 114G12

444G42 477G50

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

(1) 78G10 (2) 78.2G1.5

326G42 327G6.5

–Cl

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BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

581

MgC–O

(1) 53G3 (2) 54.4G1.4 (3) 58.6G2.3

222G13 227.6G5.8 245.2G10

(1) PD (2) Re-analysis (3) CID

(1) 1989OPE/TEW (2) 1994BAU/STE (3) 1994DAL/ARM

MgOC–O

%86.5G0.9

%361.8G3.9

PD

1998CHE/WON(b)

MgC–O2

%26.1G2.5

%109.0G10.6

PD

1998CHE/WON(b)

MgCO–H

124G7

519G29

PD

1989OPE/TEW

MgC–OH

(1) 75G4 (2) 76G6

314G33 318G25

(1) PD (2) MS

(1) 1989OPE/TEW (2) 1981MUR

MgC–N2

3.1

13

Review

1994YEH/PIL

MgC(CO)x–CO xZ0 1

10.3G1.4 9.4G0.7

43.1G5.8 39.4G2.9

CID

2000AND/MUN

(1) 14.7 (2) 14.0G1.4 (2) 11.4G0.7 (2) 10.3G1.4

61.6 58.4G5.8 47.8G2.9 43.0G5.8

(1) PD (2) CID

(1) 1993YEH/WIL (2) 2000AND/MUN

(1) 24.3 (2) 25.0 (3) 29.3G3.0 (3) 22.9G1.6 (3) 18.0G2.1 (3) 11.9G2.1 (4) w10.5

101.7 104.6 122.5G12.5 95.7G6.8 75.5G8.7 49.8G8.7 w44

(1) PD (2) Review (3) CID

(1) 1992WIL/YEH(b) (2) 1997DUN (3) 2000AND/MUN

(4) Extrapolate

(4) This volume

(1) 38.0G2.8 (1) 29.6G1.6 (1) 23.4G2.1 (1) 10.9G2.5 (1) 13.6G2.8 (2) w4.7

158.9G11.6 123.9G6.8 97.8G8.7 45.4G10.6 57.0G11.6 w20

(1) CID

(1) 2000AND/MUN

(2) Extrapolate

(2) This volume

MgC(CO2)x–CO2 xZ0 1 2

MgC(H2O)x–H2O xZ0

1 2 3 N

MgC(NH3)x–NH3 xZ0 1 2 3 4 N

(continued)

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

582

Comprehensive Handbook of Chemical Bond Energies

Table 12.2.2 (continued) BDEs of MgC–X Bonds

The broken bonds (boldfaceZ dissociated fragment) MgC(CH4)x–CH4 xZ0 1

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

7.1G1.6 3.1G1.6

29.8G6.8 12.8G6.8

CID

2000AND/MUN

(1) 61G5 (2) 35.3G1.6

255G21 147.6G6.8

(1) FT MS (2) CID

(1) 1988OPE/TEW (2) 2000AND/MUN

1

(2) 29.0G1.6

121.2G6.8

2

(2) 22.1G2.1

92.3G8.7

MgC–C2H2

17.4

73.0

PD

1999RED/DUN

MgC–C2H4

16.1G4.6

67.5G19.3

PD

1998CHE/WON

MgC–EtOH

(1) 63G5 (2) 36.7G1.6 (1) 64G5 (2) 37.8G1.6 (1) 65G5 (2) 38.5G1.6 (1) 65G5 (2) 38.7G1.6

264G21 153.4G6.8 268G21 158.2G6.8 272G21 161.1G6.8 272G21 162.1G6.8

(1) FT MS (2) Recal.

(1) 1988OPE/TEW (2) 2000AND/MUN

(1) 63G5 (2) 37.1G1.6 (1) 65G5 (2) 38.5G1.6 (1) 66G5 (2) 39.4G1.6

264G21 155.3G6.8 272G21 161.1G6.8 276G21 165.0G6.8

(1) FT MS (2) Recal.

(1) 1988OPE/TEW (2) 2000AND/MUN

(1) 67G5 (2) 41.3G1.6 (1) 68G5 (2) 42.4G1.6

280G21 172.7G6.8 285G21 177.5G6.8

(1) FT MS (2) Recal.

(1) 1988OPE/TEW (2) 2000AND/MUN

MgC(MeOH)x –MeOH xZ0

–n-PrOH –i-PrOH –n-BuOH

MgC–MeCHO –EtCHO –n-PrCHO

MgC–MeCOMe –MeCOEt

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

MgC–EtOEt

583

(1) 66G5 (2) 39.9G1.6 (1) 66G5 (2) 40.1G1.6

276G21 166.9G6.8 276G21 167.9G6.8

(1) FT MS (2) Recal.

(1) 1988OPE/TEW (2) 2000AND/MUN

(1) %26.9 (2) 32.5G2.3 (3) 37.1 (3) !32.3

%112 136.0G9.6 155.2 !135

(1) PD (2) CID (3) Kinetics

(1) 1992WIL/YEH(b) (2) 2000AND/MUN (3) 2000GAP/DUN

MgC-(Cl)(C6H6)x –C6H6 xZ0 1

62 !32

259 !134

Kinetics

2000GAP/DUN

MgC(Cl)(L)x–L, LZmesitylene xZ0 1

O46.1 34.6

O193 145

FT-ICR

2000GAP/DUN

MgC–pyridine –pyrimidine

48.1G1.5 41.8G1.5

201.3G6.4 174.9G6.1

CID

2000ROD/STA 2001AMU/ROD

MgC–phenol –indole

38G4 46G4

159.0G16.7 192.5G16.7

Combined

1999RYZ/DUN

MgC(pyrrole)x– pyrrole xZ0 1

43.9 !26.0

183.7 !108.8

Kinetics

2000GAP/YAN

MgC–imidazole

58.3G2.1

243.9G10.4

CID

2004RAN/AMU

Mg2C(H2O)x–H2O xZ4

(2) 26.3

110.0

(1) ES MS (2) Combined

(1) 1998PES/BLA (2) 1999ROD/JOC(b)

(1) 24.6 (2) 24.2 (1) 20.3

102.9 101.3 84.9

–tetrahydrofuran

MgC(C6H6)x –C6H6 xZ0

1

5 6

(continued)

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

584

Comprehensive Handbook of Chemical Bond Energies

Table 12.2.2 (continued) BDEs of MgC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(2) 18.7 (1) 18.0 (3) 15G3 (4) 18.9G1.8 (1) 17.0 (3) 15G3 (4) 17.1G1.4 (1) 15.7 (3) 15G3 (4) 12.7G0.9 (1) 14.3 (3) 14G3 (1) 12.9 (3) 14G3 (1) 12.3 (1) 12.1 (5) w10.5

78.2 75.3 62.8G12.6 79.1G7.7 71.1 62.8G12.6 71.4G5.8 65.7 62.8G12.6 53.1G3.9 59.8 58.6G12.6 54.0 58.6G12.6 51.5 50.6 w44

Mg2C(Me2CO)x– Me2CO xZ5 6

22.3 13.6

Mg2C(L)x–L, LZMacAZ N-methylacetamide xZ4 5 6

25.3 22.6 19.9

7

8

9

10 11 12 13 N

Methods (reference in parentheses)

References

(3) HP MS (4) BIRD

(3) 1990BLA/JAY(b) (4) 2004WON/PAE

(5) Extrapolate

(5) This volume

93.3 56.9

ES MS

2000PES/BLA

105.9 94.7 83.3

ES MS

2000PES/BLA

12.3 CaK and CaC–X bonds 12.3.1 Ca–X bonds Table 12.3.1 BDEs of Ca–X Bonds

The broken bonds (boldfaceZ dissociated fragment) Ca–Ca

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) 4.0 (2) !10

kJ/mol 16.8 42

Methods (reference in parentheses) (1) LIF (2) EI

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

References (1) 1980VID (2) 1983WU/IHL

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

585

(3) w4 (4) 3.9 (5) 3.95G0.03

w17 16.3 16.52G0.11

(3) Spectroscopy (4) Review (5) FT spectrom.

(3) 1995GON/KHA (4) 1996SMI/YAT (5) 2002ALL/PAS

Ca–Li

20.3G2.0

84.9G8.4

EI

1983WU/IHL

Ca–Au

(1) 57.8 (2) 59.8G1.0

242 250.4G4.0

(1) Review (2) MS

(1) 1980GIN (2) 2004BAL/CIO

Ca–Al

12.6

52.7

Spectrometry

1994BEH/MOR

Ca–Ar –Kr –Xe

1.06G0.14 1.23G0.17 1.75G0.23

4.44G0.60 5.15G0.72 7.31G0.96

R2PI

1997KAU/BRE(d)

Ca–H

(1) 49.3 (2) 63.6G1.4 (3) 53.5

206.3 266.2G5.6 223.8

(1) MS (2) Spectrometry (3) Spectrometry

(1) 1968EHL/HIL (2) 1983NAR/RAJ (3) 2000URE/GOM

Ca–D

%40.6

%169.9

Est. by esp.

1979HUB/HER

(1) 126 (2) 126.5

527 529

(1) 1979ENG (2) 1996NIST

(2) 141.5

592

(1) CL (2) Derived from DfH0 in ref.

(1) 97.8G2.1 (2) 96.5

409G8.7 404

(1) 1993MEN/GAR (2) 1996NIST

(2) 116.7

488

(1) Mol. beam (2) Derived from DfH0 in ref.

(1) 74.3G2.2

310.9G9.2

(1) MS

(1) 1977HIL

Ca(F)x–F xZ0

1

Ca(Cl)x–Cl xZ0

1

Ca(Br)x–Br xZ0

(continued)

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

586

Comprehensive Handbook of Chemical Bond Energies

Table 12.3.1 (continued) BDEs of Ca–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) Derived from DfH0 in ref.

(2) 1996NIST

(1) MS (2) MS (3) Derived from DfH0 in ref.

(1) 1978KLE/HIL (2) 1992HIL/LAU (3) 1996NIST

402G17 383.3G5.0

(1) Review (2) MS

(1) 1983PED/MAR (2) 1995SAM/KAZ

(1) 74.6G4.5 (2) 80G5

312.1G18.8 335G21

(1) MS (2) Review

(1) 1964COL/GOL (2) 1974GUR/KAR

(CaO)–H

108.9

456

Derived from DfH0 in ref.

1996NIST

Ca(polycs. surf.)–H2

1.7–4.0

7.1–16.7

Review

1964HAY/TRA

(1) 92G4 (2) 97.7

385G17 409

(1) 1981MUR (2) 1996NIST

1

(2) 108.6

454

(1) HT MS (2) Derived from DfH0 in ref.

Ca–HCl

(1) 4.6 (2) %3.5

19.3 %14.5

(1) CL (2) Mol. beam

(1) 1992SOE/ABB (2) 1994MEN/GAR

Ca(polycs. surf.)–N2

1.5–3.8

6.3–15.9

Review

1964HAY/TRA

(2) 81.0

339

(2) 106.9

447

(1) 62.1G2.5 (2) 68.0G2 (3) 69.2

259.8G10.5 284.7G8.4 290

(3) 86.0

360

Ca–O

(1) 96.0G4.0 (2) 92.8G1.2

Ca–S

1

Ca(I)x–I xZ0

1

Ca(OH)x–OH xZ0

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

587

Ca–CH3

46%

192%

Spectroscopy

1987BRA/BER

Cl2Ca–ethleneurea –2(ethyleneurea) –ethylenethiourea –2(ethylenethiourea) –propyleneurea –2(propyleneurea)

48.1 36.3 48.1

201.2 151.8 201.1

Calorimetry

2001FAR/AIR

37.1

155.2

46.5 34.4

194.5 143.8

12.3.2 Ca+–X bonds Table 12.3.2 BDEs of CaD–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CaC–Ca

24.9

104.1

Derived

1996SMI/YAT

CaC–Au

73G7

306G29

Derived from IP in ref.

2004BAL/CIO

CaC–Ne

1.18G0.01

4.95G0.06

REPD

2000RED/PUL

CaC–Ar

(1) (2) (3) (4)

3.4 2.89G0.29 2.99 3.10G0.14

14.4 12.09G1.20 12.50 12.99G0.60

(1) (2) (3) (4)

PD PD Review R2PI

(1) (2) (3) (4)

1995BUT/BEL 1996PUL/SCU 1997DUN 1997KAU/BRE(b)

CaC–Kr

(1) (2) (3) (4)

3.3 4.89G0.43 5.27 4.45G0.17

13.8 20.46G1.79 22.04 18.60G0.72

(1) (2) (3) (4)

PD PD Review R2PI

(1) (2) (3) (4)

1995BUT/BEL 1996PUL/SCU 1997DUN 1997KAU/BRE(b)

CaC–Xe

(1) 7.46G0.43

31.23G1.79

(1) PD

(1) 1996PUL/SCU

(continued)

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

588

Comprehensive Handbook of Chemical Bond Energies

Table 12.3.2 (continued) BDEs of CaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(2) 7.07 (3) 6.07G0.23

29.58 25.38G0.96

(2) Review (3) R2PI

(2) 1997DUN (3) 1997KAU/BRE(b)

CaC–H

(1) 47.7 (2) 46.4G2.8 (3) 59.3G2.4

199.7 194G12 248.2G10

(1) Spectroscopy (2) GIB MS (3) Derived from IP in ref.

(1) 1982MCF/SCH (2) 1988GEO/ARM (3) 1996NIST

CaC–F

(1) 129G10 (2) 134.4G2.3 (3) 133.0G2.0

540G42 562.4G9.6 556.5G8.4

(1) Derived (2) Derived (3) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1994JAK/HAR (3) 1996NIST

CaC–Cl

(1) 97G10 (2) 103.6G2.9

406G42 433.4G12

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

CaC–Br

99.8G2.4

417.6G10

Derived from IP in ref.

1996NIST

70.2G2.6

293.7G10.8

CaC–O

(1) (2) (3) (4)

241G48 318.4G9.6 348G5 323

(1) (2) (3) (4)

(1) (2) (3) (4)

CaC–Al

34.6

144.7

Spectrometry

1994BEH/MOR

CaCO–H

150G14

627G58

High temp. MS

1981MUR

CaC–OH

(1) 106G7 (2) 104.0G3.5

444G29 435.1G14.5

(1) High temp. MS (2) Tandem MS

(1) 1981MUR (2) 1983MUR

–I

58G12 76.1G2.3 83.2G1.2 77.2

High temp. MS Tandem MS GIB MS Derived

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

References

1981MUR 1983MUR 1990FIS/ELK 2004LAV/BLA

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

CaC–N2

589

(1) 4.49 (2) 5.0G1.4

18.79 21.0G6.0

(1) Review (2) PD

(1) 1997DUN (2) 1998PUL/RED

CaC(H2O)x–H2O xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

117.2 100.4 90.0 78.2 73.2 w44

(1) HP MS

(1) 1987KOC/CON

(2) Extrapolate

(2) This volume

CaC(OH)–H2O

34.4

144

MS

1982BUR/HAY

CaC–OCH2

w20.8G4.6

w86.8G19.3

PD

2003LU/WON

CaC–C2H2

18.6G5.0

77.8G20.9

PD

1998FRA/PUL

CaC(C6H6)x–C6H6 xZ0 1

32 30

134 126

Derived

2002GAP/DUN

CaC(Cl)(C6H6)x– C6H6 xZ0 1

44 36

184 151

Derived

2002GAP/DUN

CaC(Br)(C6H6)x– C6H6 xZ0 1

39 32

163 134

Derived

2002GAP/DUN

CaC(L)x–L, LZmesitylene xZ0

32

134

FT-ICR

2000GAP/DUN

28 24 21.5 18.7 17.5 w10.5

(continued)

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

590

Comprehensive Handbook of Chemical Bond Energies

Table 12.3.2 (continued) BDEs of CaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment) 1

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

30

125

CaC(Cl)(L)x–L, LZmesitylene xZ0 1

w46 37

w193 155

FT-ICR

2000GAP/DUN

CaC(Br)(L)x–L, LZmesitylene xZ0 1

39 32

163 134

FT-ICR

2000GAP/DUN

CaC–imidazole

44.5G0.9

186.3G3.9

CID

2004RAN/AMU

(1) (2) (1) (2) (3) (1) (2) (3) (3) (4) (3) (4) (5) (3) (4) (5) (3) (5) (3) (5) (3) (3) (6)

110.0G5.9 111.7 91.6G5.9 92.0 105.9 68.6G5 70.3 70.7 67.4 73.3G5.8 64.0 64.6G5.8 62.8G12.6 60.7 49.2G5.8 62.8G12.6 55.6 58.6G12.6 54.4 58.6G12.6 51.9 49.8 w44

(1) IR radiation (2) Combined

(1) 1998ROD/JOC (2) 1998ROD/JOC(b)

(3) ES MS

(3) 1998PES/BLA

(4) BIRD

(4) 2004WON/PAE

(5) HP MS

(5) 1990BLA/JAY(b)

(6) Extrapolate

(6) This volume

Ca2C(H2O)x–H2O xZ4 5

6

7 8

9

10 11 12 13 N

26.3G1.4 26.7 21.9G1.4 22.0 25.3 16.4G1.2 16.8 16.9 16.1 17.5G1.4 15.3 15.5G1.4 15G3 14.5 11.8G1.4 15G3 13.3 14G3 13.0 14G3 12.4 11.9 w10.5

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

591

Ca2C(Me2CO)x– Me2CO xZ5 6

24.2 11.6

101.3 48.5

ES MS

2000PES/BLA

Ca2C(L)x–L, LZMacAZ N-methylacetamide xZ5 6 7 8

23.7 19.6 17.9 17.5

99.2 82.0 74.9 73.2

ES MS

2000PES/BLA

Ca2C–a-amlase

3.8

16.0

UV

2002SAB

12.4 SrK and SrC–X bonds 12.4.1 Sr–X bonds Table 12.4.1 BDEs of Sr–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

Sr–Sr

(1) 3.7G0.1 (2) 3.98G0.29

15.5G0.4 16.64G1.12

Spectroscopy

(1) 1982GER/MOE (2) 1984GER/MOL

Sr–Au

(1) 88 (2) 63G10

368 264G42

Review

(1) 1973LIT/SPA (2) 1974GUR/KAR

Sr–H –D

39.2G2 40.1

164G8 167.7

Spectroscopy

1979HUB/HER

(1) 129.5G1.6 (2) 126.8

541.8G6.7 531

(1) MS (2) CL

(1) 1968HIL (2) 1979ENG

Sr(F)x–F xZ0

References

(continued)

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

592

Comprehensive Handbook of Chemical Bond Energies

Table 12.4.1 (continued) BDEs of Sr–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(3) Derived from DfH0 in ref.

(3) 1996NIST

Derived from DfH0 in ref.

1996NIST

(1) MS (2) Derived from DfH0 in ref.

(1) 1977HIL (2) 1996NIST

(1) MS (2) Derived from DfH0 in ref.

(1) 1978KLE/HIL (2) 1996NIST

426G17 426.3G6.3

(1) Review (2) MS

(1) 1983PED/MAR (2) 1994SAM/KAZ

(1) 75.0G4.5 (2) 80.9G4

314G18.8 338.5G16.7

MS

(1) 1964COL/GOL (2) 1967CAT/JOH

Sr–Se

60.0G3

251.0G12.6

MS

1966BER/CHU

(SrO)–H

98.0

410

Derived from DfH0 in ref.

1996NIST

(3) 128.6

538

(3) 131.7

551

97.8

409

112.5

471

(1) 79.6G2.2 (2) 87.2

333.0G9.2 365

(2) 102.7

430

(1) 64.5G1.4 (2) 72.0

269.9G5.9 301

(2) 83.9

351

Sr–O

(1) 101.8G4.0 (2) 101.9G1.5

Sr–S

1

Sr(Cl)x–Cl xZ0 1

Sr(Br)x–Br xZ0

1

Sr(I)x–I xZ0

1

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

Sr(OH)x–OH xZ0

1

Sr–CH3

(1) 92G4 (2) 97.2

385G17 407

(2) 102.0

427

43%

180%

593

(1) HT MS (2) Derived from DfH0 in ref.

(1) 1981MUR (2) 1996NIST

Spectroscopy

1987BRA/BER

12.4.2 SrC–X bonds Table 12.4.2 BDEs of SrD–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

SrC–Sr

(1) 25.9G0.4 (2) 26.3

108.5G1.6 109.8

(1) R2PI (2) Derived

(1) 1992DUG/CHE (2) 1996SMI/YAT

Sr2C(Sr)16–Sr

34.6G6.9

144.7G28.9

PD

1998BRE/CAH

SrC–Ne

1.08

4.52

PD

1997LUD/PRE

SrC–Ar

3.18G0.70

13.32G2.92

Photofrag.

1996LUD/VEL

SrC–Kr

4.33G1.66

18.13G6.94

PD

1998PRE/FEN

SrC–Xe

6.5G1.5

27.0G6.3

Photofrag.

2001MAS/SFO

SrC–H

50.0G1.3

209G5

CID

1993DAL/CRE

SrC–F

(1) 147G12 (2) 139.8G2.4

615G50 584.8G10

(1) 1974GUR/KAR (2) 1996NIST

(1) 98G10 (2) 102G2

410G42 427G8.4

(1) Derived (2) Derived from IP in ref.

–Cl

References

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 12.4.2 (continued) BDEs of SrC–X Bonds

The broken bonds (boldfaceZdissociated fragment) SrC–Br

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

90.3G2.0

378.1G8.4

73.7G2.3

308.2G9.6

SrC–O

(1) (2) (3) (4)

SrCO–H

References

Derived from IP in ref.

1996NIST

279.8G19.3 296.2G14.5 339G6 298.7

(1) (2) (3) (4)

(1) (2) (3) (4)

141G9

589G39

High temp. MS

1981MUR

SrC–OH

(1) 106.1G4.6 (2) 105.4G2.3

443.8G19.3 440.9G9.6

(1) High temp. MS (2) Tandem MS

(1) 1981MUR (2) 1983MUR

SrC–CO

4.9

20.3

Photofrag.

2002FAR/FIL

SrC–CO2

10.0

41.9

PD

2005MAS/VEL

(1) (1) (1) (1) (2) (1) (2) (1) (2) (1) (1) (3)

144.3 127.6 107.5 93.3 100.0 86.2 87.4 76.6 71.5 72.4 68.6 w44

(1) HP MS

(1) 1976TAN/LIA

(2) Combined

(2) 1999ROD/JOC(b)

(3) Extrapolate

(3) This volume

–I

SrC(H2O)x–H2O xZ0 1 2 3 4 5 6 7 N

66.9G4.6 70.8G3.5 81.0G1.4 71.4

34.5 30.5 25.7 22.3 23.9 20.6 20.9 18.3 17.1 17.3 16.4 w10.5

High temp. MS Tandem MS CID Derived

1981MUR 1983MUR 1994DAL/ARM 2004LAV/BLA

SrC(OH)–H2O

29.9

125

MS

1982BUR/HAY

SrC–CH3OD

23

96

PD

2002LEE/QIA

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

595

SrC(C6H6)x–C6H6 xZ0 1

28 28

117 117

Derived

2002GAP/DUN

SrC(Cl)(C6H6)x–C6H6 xZ0 1

37 36

155 151

Derived

2002GAP/DUN

SrC(Br)(C6H6)x–C6H6 xZ0 1

37 30

155 126

Derived

2002GAP/DUN

SrC(L)x–L, LZmesitylene xZ0 1

28 28

115 115

FT-ICR

2000GAP/DUN

SrC(Cl)(L)x–L, LZmesitylene xZ0 1

39 35

163 146

FT-ICR

2000GAP/DUN

SrC(Br)(L)x–L, LZmesitylene xZ0 1

37 30

155 126

FT-ICR

2000GAP/DUN

95.0 87.4 71.1 71.5 67.4 64.9 62.8G12.6 62.3 58.6G12.6 59.4 58.6G12.6 57.3 58.6G12.6 54.4 w44

(1) ES MS (2) Combined

(1) 1998PES/BLA (2) 1999ROD/JOC(b)

(3) HP MS

(3) 1990BLA/JAY(b)

(4) Extrapolate

(4) This volume

Sr2C(H2O)x–H2O xZ5 6 7 8 9 10 11 12 N

(1) (2) (1) (2) (1) (1) (3) (1) (3) (1) (3) (1) (3) (1) (4)

22.7 20.9 17.0 17.1 16.1 15.5 15G3 14.9 14G3 14.2 14G3 13.7 14G3 13.0 w10.5

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Comprehensive Handbook of Chemical Bond Energies

12.5 BaK and BaC–X bonds 12.5.1 Ba–X bonds Table 12.5.1 BDEs of Ba–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ba–Rh

62.0G6.0

259.4G25

MS

1978GIN/CHO

Ba–Pd

53.0G1.2

221.8G5.0

MS

1978GIN/CHO

Ba–Au

60.9G2.4

254.8G10

MS

1980GIN

Ba–H –D

45.9 %46.3

192.0 %193.7

Spectroscopy

1979HUB/HER

(1) 140.3G1.6 (2) 136.6 (3) 138.8

587G6.7 571.5 580.6

(1) 1968HIL (2) 1979ENG (3) 1996NIST

(3) 134.1

561

(1) MS (2) CL (3) Derived from DfH0 in ref.

(1) 104.2G2 (2) 105.8

436.0G8.4 443

(1) 1977HIL (2) 1996NIST

(2) 114.2

478

(1) MS (2) Derived from DfH0 in ref.

(1) 85.5G2.2 (2) 86.7G2 (3) 96.0

357.7G9.2 362.8G8.4 402

(1) 1977HIL (2) 1978EST/ZAR (3) 1996NIST

(3) 101.8

426

(1) MS (2) CL (3) Derived from DfH0 in ref.

Ba(F)x–F xZ0

1

Ba(Cl)x–Cl xZ0

1

Ba(Br)x–Br xZ0

1

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BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

Ba(I)x–I xZ0

1

(1) (2) (3) (4) (5)

72.9G2 78.5G0.5 78.6G2 77.1G1.5 78.5

305.0G8.4 328.4G2.1 328.9G8.4 322.6G6.3 328

(1) (2) (3) (4) (5)

CL LIF Recommend MS Derived from DfH0 in ref.

(1) (2) (3) (4) (5)

597

1978EST/ZAR 1986JOH/ALL 1990VAC/ZHA 1992HIL/LAU 1996NIST

(5) 87.8

367

Ba–O

134.3G3.2

562G13.4

Review

1983PED/MAR

Ba–S

(1) 95.6 G4.5 (2) 100G5

400.0G18.8 418G21

(1) MS (2) Review

(1) 1964COL/GOL (2) 1974GUR/KAR

(BaO)–H

76.6

320

Derived from DfH0 in ref.

1996NIST

(1) 107 (2) 107G4 (3) 105.8

448 448G17 443

(1) 1960STA/BER (2) 1981MUR (3) 1996NIST

(1) 99 (3) 104.5

414.2 437

(1) MS (2) HT MS (3) Derived from DfH0 in ref.

(BaO)–BaO

89G11

372G46

Review

1967DRO/GOL

Ba(polycs. surf.)–N2

2–4

8.4–16.7

Review

1964HAY/TRA

Ba–OCH3

87.6G2.3

366.6G9.6

CL

1993PUJ/SUB

Ba–C2

139.0G3.5

581.7G14.8

MS

1985GIN/CHO

Ba(OH)x–OH xZ0

1

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598

Comprehensive Handbook of Chemical Bond Energies

12.5.2 BaC–X bonds Table 12.5.2 BDEs of BaD–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

BaC–Ar

2.83

11.85

Spectroscopy

1995PAN/WIL

BaC–D

58.6G2.3

245.2G9.6

CID

1980ARM/BEA(c)

BaC–F

(1) 147G10 (2) 148.2G2.3 (3) 153G7

615G42 620.2G9.6 640G29

(1) Derived (2) Derived (3) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1994JAK/HAR (3) 1996NIST

(1) 111G10 (3) 111.9G2.4

464G42 468.2G10

100.0G2.4

418G10

Derived from IP in ref.

1996NIST

80.1G2.4

335G10

(1) 94.5G4.6 (2) 105.5G3.6

395.6G19.3 441.4G15

(1) 1981MUR (2) 1996NIST

(3) 92.8

388

(1) High temp. MS (2) Derived from IP in ref. (3) Derived

BaCO–H BaC–OH

133.8G9 126.8G4.6

560G39 530.7G19.3

High temp. MS

1981MUR

Ba2C(H2O)x–H2O xZ3

(2) 26.4

110.5

(1) ES MS (2) Combined

(1) 1998PES/BLA (2) 1999ROD/JOC

(1) (2) (1) (2) (1) (2)

100.0 90.8 82.8 77.8 70.7 66.9

–Cl

BaC–Br –I

BaC–O

4 5 6

23.9 21.7 19.8 18.6 16.9 16.0

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

(3) 2004LAV/BLA

BDEs of Be(BeC)–, Mg(MgC)–, Ca(CaC)–, Sr(SrC)–, Ba(BaC)–, and Ra–X Bonds

7 8 9 10 11 12 13 N

(1) (1) (1) (1) (1) (1) (1) (3)

15.8 15.1 14.1 13.4 12.4 11.6 10.9 w10.5

66.1 63.2 59.0 56.1 51.9 48.5 45.6 w44

(3) Extrapolate

599

(3) This volume

12.6 Ra–X bonds Table 12.6 BDEs of Ra–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Ra–Cl

82G18

kJ/mol

Methods (reference in parentheses)

References

343G75

Spectroscopy

1968GAY

7366—CHAPTER 12—3/2/2007—15:04—CRCPAG—15368—XML MODEL B – pp. 571–599

chapter thirteen

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X bonds 13.1 ScK and ScC–X bonds 13.1.1 Sc–X bonds Table 13.1.1 BDEs of Sc–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

Sc–Sc

(1) 38.0G5 (2) 38.7 (3) 30.9 (4) 39.0G5

159G21 162 129.1 163G21

(1) (2) (3) (4)

Sc–Rh –Au

106G2.6 66.9G9.6

444G11 280G40

MS

1989CHA/GIN

Sc–H

(1) 47.5G2 (2) 48.3G2 (3) 49G4

198.7G8 202G8 205G17

(1) MS (2) Review (3) Recommend.

(1) 1981KAN/MOO (2) 1990SIM/BEA (3) 1991ARM/SUN

(1) 140.8G3 (2) 143.2G3.2 (1) 140.3G5 (2) 148.8G4.1

589G13 599.1G13.4 587G21 622.6G17.2

MS

(1) 1967ZMB/MAR(b) (2) 1995HIL/LAU

Sc(F)x–F xZ0 1

MS Review Raman MS

References (1) (2) (3) (4)

1974GUR/KAR 1979MIE/GIN 1984MOS/DIL 1989CHA/GIN

(continued)

601

7366—CHAPTER 13—3/2/2007—19:03—BSARAVANAN—15369—XML MODEL B – pp. 601–665

602

Comprehensive Handbook of Chemical Bond Energies

Table 13.1.1 (continued) BDEs of Sc–X Bonds

The broken bonds (boldfaceZ dissociated fragment) 2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 157G7 657G29 (2) 155.7G6.4 651.4G26.8

Sc–Cl

79.1

331

Est. by exp.

1979HUB/HER

Sc–Br

106G15

444G63

Review

1974GUR/KAR

Sc–O

(1) (2) (3) (4) (5)

162.5G2.4 162.8G2.2 160.3G2.1 160.0G3.2 160.5G0.2

680G10 681G9 670.8G8.9 669.4G13.5 671.4G1.0

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Sc–S

(1) 114.3G3.0 (2) 112.0G4.5

478.2G12.6 468.6G18.8

MS

(1) 1975STE/CAT (2) 1976TUE/LAA

Sc–Se –Te

92G4 69G4

385G17 289G17

Review

1974GUR/KAR

Sc–N

111G20

464G84

Review

1974GUR/KAR

Sc–C –C2

(1) (1) (2) (2) (2) (2)

444G21 572 592G25 460G40 579G45 556G60

(1) Review

(1) 1990SIM/BEA

(2) Derived

(2) 1989CHA/GIN

MS

1989KIN/GIN

–C3 –C4 –C5

Sc–Si –Ge

106.1G5 136.7 141G6 110G10 138G11 133G14

54.3G3.3 64.5G2.6

227.2G14 270G11

Re-evaluated Review Equilibrium Spectroscopy LIF

7366—CHAPTER 13—3/2/2007—19:03—BSARAVANAN—15369—XML MODEL B – pp. 601–665

1989CHA/GIN 1990SIM/BEA 1999ROS/WAH 1999RED/AHA 2001LUC/VET

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

603

Sc–B

65G15

272G63

Review

1974GUR/KAR

F3Sc–LiF –NaF –KF –RbF –CsF

75.4 78.2 84.4 86.3 w81.3

315.5 327.0 353.1 361.0 w340

Derived

1985ZHU/NIK

Sc–CH3

28G7

116G29

GIB MS

1990ARM

Sc–C6H6

14.5G6.0

60.8G25.0

Derived

1999KUR/TAK

13.1.2 ScC–X bonds Table 13.1.2 BDEs of ScD–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) Sc+–Fe

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

(1) 48G5

201G21

(1) PD

(2) 49G6

205G25

(2) Ion reactions

(1) 54.9G4 (2) 56.2G2

229.7G17 235G8

(1) Ion beam (2) Review

References 1987HET/FRE

Sc+(H)x–H xZ0

(1) 1984TOL/BEA (2) 1987SCH/GOD

(3) 57.1G2.1

239G9

(3) GIB MS

(3) 1989SUN/ARM

(4) 50.9G1.4

213.0G5.8

(4) GIB MS

(4) 1993DAL/CRE

(3) 58.3G3.7

244G15

(H)Sc+–D

60G4

251G17

Est. by exp.

1999CRE/BEA

Sc+–F

(1) 147G11 (2) 144.6G7.6

615G46 605G32

(1) Derived (2) Derived from

(1) 1974GUR/KAR (2) 1996NIST

1

IP in ref.

(continued)

7366—CHAPTER 13—3/2/2007—19:03—BSARAVANAN—15369—XML MODEL B – pp. 601–665

604

Comprehensive Handbook of Chemical Bond Energies

Table 13.1.2 (continued) BDEs of ScC–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds fragment) Sc+–2H

Methods

reference in parentheses)

(boldfaceZdissociated

kcal/mol

(reference in

kJ/mol

parentheses)

References

(1) 115.5G3.0

483G13

(1) GIB MS

(1) 1989SUN/ARM

(2) 111.6G1.2

467G5

(2) Review

(2) 1996ARM/KIC

xZ0

5.5G0.3

23.0G1.3

Equilibrium

1994BUS/KEM

1

6.9G0.3

28.9G1.3

2

5.4G0.3

22.6G1.3

3

5.4G0.3

22.6G1.3

MS

1986TSI/GUS

1991CLE/ELK

Sc+(H2)x–H2

(F2Sc+)(NaF)x–NaF xZ1

83

347

2

72

301

3

67

280

77.9G1.4

326G6

GIB MS

(1) R93.4G2.5

R391G10

GIB MS

(2) 98.5G5.3

412G22

Sc+–C

Sc+–CH2

(1) 1987SUN/ARI (2) 1989SUN/ARM

Sc+(CH3)x–CH3 xZ0 1

(H)Sc+–CH3

Sc+–C2H2

–C2H4

(1) 59.0G3

247G13

(2) 55.7G2.4

233G10

GIB MS

(2) 1996ARM/KIC

(3) 55.0G2.6

230.1G10.9

(3) 1990SUN/ARM(b)

58.2G2.4

243.5G10.0

GIB MS

(1) 1987SUN/ARI

1990SUN/ARM(b)

(1) 77.9G2.3

326G10

(1) GIB MS

(1) 1987SUN/ARI

(2) 52G3

218G13

(2) PD

(2) 1992RAN/FRE

(3) 57G5

240G20

(3) Review

(3) 1996ARM/KIC

(1) R35.0G1.2

R146G5

(3) R31

R131

7366—CHAPTER 13—3/2/2007—19:03—BSARAVANAN—15369—XML MODEL B – pp. 601–665

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

(4) 32

133.9

(3) 110.9G1.2

464G5

Sc+–C4H6

R29

Sc+–C6H4

Sc+–C6H6

605

(4) Review

(4) 1998SCH/SCH

R121

Ion reactions

1990SUN/ARM

88G5

368G21

PD

1991HUA/HIL

53G5

222G21

FT-MS

1988LEC/FRE

xZ0

58

243

FT-ICR

2002GAP/DUN

1

44

184

FT-ICR

2002GAP/DUN

FT-ICR

2002GAP/DUN

FT-ICR

2002GAP/DUN

FT-ICR

2002GAP/DUN

–(CH3)2

(Cl)Sc+(C6H6)x–C6H6

(Br)Sc+(C6H6)x–C6H6 xZ0

60

251

1

43

180

(Cl)2Sc+(C6H6)x–C6H6 xZ0

58

243

1

34

142

(I)Sc+(C6H6)x–C6H6 xZ0

59

247

1

43

180

(I)2Sc+(C6H6)x–C6H6 xZ0

56

234

1

40

167

Sc+(O)x–O xZ0

(1)164.6G1.3

689G5

1

(2) 39.7G4.4

166G18

GIB MS

(1) 1993CLE/ARI (2) 1992CLE/DAL

(continued)

7366—CHAPTER 13—3/2/2007—19:03—BSARAVANAN—15369—XML MODEL B – pp. 601–665

606

Comprehensive Handbook of Chemical Bond Energies

Table 13.1.2 (continued) BDEs of ScC–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Sc+(S)–O

90.6G7.4

379.2G30.9

Derived

2006KRE/SCH

Sc+–O2

86.3

361

Review

2006SCH

Sc+–OH

(1) 87.8

367.4

(1) TQ-MS

(1) 1989MAG/DAV(b)

(2) 119.2G2.1

499G9

(2) GIB MS

(2) 1993CLE/ARI

(3) 121.8G3.0

509.4G12.6

(3) FAB

(3) 1993MCC/LEB

Sc+–H2O

31.4

131

TQ-MS

1989MAG/DAV(b)

Sc+–OCD2

39G5

163G21

FT-ICR

1999CRE/BEA

43G5

178G21

Ion reactions

(1) 2000KRE/SCH

–OCHCH3 –CD3OH

30G5

126G21

–CH3CH2OH

35G5

146G21

(1) 114.6G1.2

479.5G4.8

(2) 126.6G4.2

529.7G17.4

Sc+(O)–S

49.3G9.7

206.5G40.5

Derived

2006KRE/SCH

Sc+(S)–S

88.1G5.7

368.6G65.6

Derived

2006KRE/SCH

Sc+–CS

(1) 31.8G1.8

133.1G7.7

Ion reactions

(1) 2000KRE/SCH

(2) 32.7G1.8

137.0G7.7

Sc+–Se

113.7G2.0

475.8G8.4

Derived from IP in ref.

1996NIST

Sc+–NH

(1) 119.0G2.3

498G10

(1) GIB MS

(1) 1990CLE/SUN

(2) 115.4G2.3

483G10

(2) Review

(2) 1996ARM/KIC

Sc+–S

(2) 2006KRE/SCH

(2) 2006KRE/SCH

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

–NH2

Sc+–pyridine –pyrimidine

Sc+–imidazole

Sc+–Si

(1) 85.1G1.6

356G7

(2) 82.9G1.2

347G5

55.5G2.5

232.4G10.3

51.4G2.2

215.2G9.0

R44.6G1.2

R186.7G5.1

%65.2G2.1

%272.8G8.8

57.9G2.5

242.3G10.5

–SiH –SiH2

53.7G2.5 50.0G1.8

224.7G10.5 209.2G7.5

–SiH3

40.6G3.7

169.9G15.5

108G7

452G29

Sc2+–OH

CID

607

2000ROD/STA 2001AMU/ROD

CID

2004RAN/AMU

Ion reactions

1995CHE/ARM(c)

FAB

1993MCC/LEB

13.2 YK and YC–X bonds 13.2.1 Y–bonds Table 13.2.1 BDEs of Y–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Y–Y

(1) 38 (2) 38G5 (3) w65G9

160 160G21 w270G39

(1) Review (2) MS (3) Spectroscopy

(1) 1979MIE/GIN (2) 1989CHA/GIN (3) 2002FAN/CHE

Y–La

46G5

192G21

Review

1974GUR/KAR

Y–Co

60.64G0.02

253.71G0.10

Spectrometry

1994ARR/BLU

Y–Rh

106.6G2.6

446G11

MS

1989CHA/GIN (continued)

7366—CHAPTER 13—3/2/2007—19:04—BSARAVANAN—15369—XML MODEL B – pp. 601–665

608

Comprehensive Handbook of Chemical Bond Energies

Table 13.2.1 (continued) BDEs of Y–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Y–Ir

(1) 110.4G4.6 (2) 109.2G3.6

461.9G9.6 457G15

MS

(1) 1986MOR (2) 1989CHA/GIN

Y–Ni

67.86G0.02

283.92G0.10

Spectrometry

1994ARR/BLU

Y–Pd –Pt

57.6G3.6 113.3G2.9

241G15 474G12

MS

1989CHA/GIN

Y–Au

74.1G2.9

310G12

MS

1989CHA/GIN

Y(F)x–F xZ0 1 2

163.8G3.2 145.6G3.2 151.6G4.7

685.3G13.4 609.2G13.4 634.3G19.7

MS

1995HIL/LAU

Y–Cl –Br

125G20 115G20

523G84 481G84

Review

1974GUR/KAR

Y–I

101.0G3

422.6G12.5

Spectroscopy

1982RED/RAO

(1) (2) (3) (4) (5)

719G10 719G11 692.5G17 701.7G14.5 714.1G10.2

(1) (2) (3) (4) (5)

1975STE/CAT(b)

Y(O)x–O xZ0

1

Y–S

171.8G2.4 171.8G2.6 165.5G4.2 167.7G3.5 170.7G2.4

(6) 95.5G5

399G21

(1) Re-evaluated (2) Review (3) Spectroscopy (4) Spectroscopy (5) Derived from DfH0 in ref. (6) Ion reactions

126.3G2.5

528.4G10.5

MS

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1989CHA/GIN 1990SIM/BEA 1999LIN/SIM 1999RED/AHA 2004HEY/CHA

(6) 1992CLE/DAL

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

609

Y–Se –Te

104G3 81G3

435G13 339G13

Review

1974GUR/KAR

Y–N

114G15

477G63

Review

1974GUR/KAR

Y–C

(1) (2) (1) (3) (3) (3) (3)

418G63 418G14 638 665G40 483G55 649G55 497G60

(1) Review (2) MS

(1) 1990SIM/BEA (2) 1992SHI/PEL

(3) Derived

(3) 1989CHA/GIN

–C2 –C3 –C4 –C5

100G15 99.9G3.3 152.5 159G10 115G13 155G13 119G14

Y–Si –Ge

61.7G4 66.7G2.6

258G17 279G11

MS

1989CHA/GIN

Y–B

69G15

289G63

Review

1974GUR/KAR

Y(polycr. surf.)–O2

264.6

1107

Calorimetry

1988CER/KOV

(YO)–YO

108G11

452G46

Review

1967DRO/GOL

Y–CHO

58–73

243–305

Mol. beam

1999STA/HIN

F3Y–LiF –NaF –KF –RbF –CsF

w70.7 w80.0 w82.5 w83.4 w81.3

w296 w335 w345 w349 w340

Derived

1985ZHU/NIK

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Comprehensive Handbook of Chemical Bond Energies

13.2.2 YC–X bonds Table 13.2.2 BDEs of YD–X Bonds

The broken bonds (boldfaceZ dissociated fragment) Y+–Y –Pt

Y+(H)x–H xZ0 1

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

67G5

281G21

111G46

466G192

62.3G1.4 65.0G2.1

260.5G5.8 272G9

Methods (reference in parentheses)

References

Derived from IP in ref.

1996NIST

GIB MS

1989SUN/ARM

Y+–2H

(1) 127.3G1.6 533G7 (2) 123.3G1.2 516G7

GIB MS

(1) 1989SUN/ARM (2) 1996ARM/KIC

Y+–F

(1) 142G12 (2) 162G5

594G50 677G21

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

Y+–C –CH2 –CH3

(1) 67.1G2.8 (2) 95.2G3 (2) 59.5G1.2

281G12 398G13 249G5.0

Ion reactions

(1) 1996SIE/CHE(b) (2) 1989SUN/ARM

Y+–C2H2

(1) (2) (1) (3)

251G29 218G13 R109 O138

(1) GIB MS (2) PD

(1) 1989SUN/ARM (2) 1992RAN/FRE

(3) FT-MS

(3) 1987HUA/WIS

–C2H4

60G7 52G3 R26 O33

Y+NH–C2H4

O42

O176

Derived

1996RAN/HIL

Y+–C3H4 –C3H6 –C4H6

O71 O31 O57

O297 O130 O238

FT-MS

1987HUA/WIS

Y+–C6H6

54G5

226G21

Ion reactions

1996RAN/HIL

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds Y+(O)x–O xZ0

1

(1) (2) (3) (3) (4) (5)

167.9G4.2 171.6G6 172.1 43.5 40.5G3.7 32.3G11.5

611

702.5G17 718G25 720 182 170G15 135G48

(1) CID (2) CID (3) Review

(1) 1996SIE/CHE(b) (2) 2002JAC/KIN (3) 2006SCH

(4) CID (5) CID

(4) 1992CLE/DAL (5) 1999SIE/ARM(b)

Y+–O2

94.9

397

Review

2006SCH

Y+(O)x–CO xZ0 1 2

7.1G2.5 16.4G0.9 15.9G0.7

29.9G10.6 68.5G3.9 66.6G2.9

CID

1999SIE/ARM(b)

Y+(O)–CO2

20.5G1.2

86G5

Ion reactions

1999SIE/ARM(b)

Y+–S

127.6G2

533.9G8

Ion reactions

2003ARM

Y+–CS

32.7G1.9

137G8

Ion reactions

2000ROD/ARM(b)

Y+–Te

86G23

360G96

Derived from IP in ref.

1996NIST

Y+–Si –SiH –SiH2 –SiH3

58.1G3 63.6G3.7 R55.1G1.6 49.1G3.7

243G13 266G16 R231G7 205G16

GIB MS

1995KIC/ARM(c)

Y+–NH

O101

O423

FT MS

1996RAN/HIL

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Comprehensive Handbook of Chemical Bond Energies

13.3 LaK and LaC–X bonds Table 13.3 BDEs of La– and LaD–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

La–La

(1) 58.6 (2) 59.0G5 (3) 58.5

245 247G21 244.9

(1) Review (2) MS (3) Spectroscopy

(1) 1979MIE/GIN (2) 1989CHA/GIN (3) 2000SHE/FAN

La–Y

46G5

192G21

Review

1974GUR/KAR

La–Rh –Ir

131.5G2.9 137.9G2.9

550G12 577G12

MS

1989CHA/GIN

La–Pt

120.7G2.9

505G12

MS

1989CHA/GIN

La–Au

(1) 80.2G2.3 (2) 109.2G6.7

335.7G9.6 457G28

(1) Review (2) MS

(1) 1986MOR (2) 1989CHA/GIN

La(F)x–F xZ0 1 2

157.5G4.1 153.2G3.2 149.2G5.4

659.0G17.2 641.0G13.4 624.3G22.6

MS

1995HIL/LAU

La–Cl –Br –I

124.7 106.7 98.4

521.6 446.2 411.7

Correlation

1999KAL/HEA

(1) (2) (3) (4) (5)

799G9.6 801G11 791.2G9.6 798 405G32

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

La(O)x–O xZ0

1

191.0G2.3 191.4G2.6 189.1G2.3 190.7 96.9G7.6

Re-evaluated Review Review Review Ion reactions

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1989CHA/GIN 1990SIM/BEA 1991COC/NYU 1994HAI 1992CLE/DAL

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

613

La–O2

244.4G2.3

1022.7G9.6

Review

1991COC/NYU

La–S

(1) 136.9G3.0 (2) 137.0G0.4 (3) 114.7

572.8G12.6 573.4G1.7 480

(1) MS (2) Spectroscopy (3) Spectroscopy

(1) 1975STE/CAT (2) 1977JON/GOL (3) 1997NAG/RAJ

La–Se

(1) 114.9G3.6 (2) 116.1G3.5

480.7G15 485.7G14.6

MS

(1) 1970BER/COP (2) 1974NAG/SHI

La–Te

(1) 92.2G3.6 (2) 86.6

385.6G15 362

MS

(1) 1970BER/COP (2) 1982GOR/FEN(b)

La–N

124G10

519G42

Review

1974GUR/KAR

La–C –C2

(1) (1) (2) (2) (2) (2)

463G20 659 669G20 497G40 641G60 527G65

(1) Review

(1) 1990SIM/BEA

(2) Derived

(2) 1989CHA/GIN

–C3 –C4 –C5

110.7G5 157.5 160G5 119G10 153G14 126G16

La–B

80G15

335G63

Review

1974GUR/KAR

F3La–LiF –NaF –KF –RbF –CsF

w60.9 w76.0 w72.7 w73.6 w71.5

w255 w318 w304 w308 w299

Derived

1985ZHU/NIK

Pt(111, surf.)/La–CO

20.8G2.3

86.8G9.6

TPD

1999RAM/RAA

(LaO)–LaO

86G10

360G42

Review

1967DRO/GOL (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

La(h5-C5Me5)2– CH(SiMe3)2

66.6G2.5

278.7G10.5

Review

1994NOL

La+–Fe

48G5

201G21

Ion reactions

1988HUA/FRE

La+–Rh

82.5G23.2

345G97

Derived from IP in ref.

1996NIST

–Ir

128G23.2

536G97

La+–Pt

124.8G18.6

522G78

Derived from IP in ref.

1996NIST

La+–Au

104.1G23

436G97

Derived from IP in ref.

1996NIST

(1) 60G10 (2) 58.1G2.1 (2) 63.6G2.8

251G42 243G9 266G12

(1) PD (2) GIB MS

(1) 1987HET/FRE (2) 1989SUN/ARM

La+(C)–H La+(CH)–H

104G11 82G7

435G46 343G29

PD

1987HET/FRE

La+–2H

(1) 121.8G1.8 (2) 117.8G1.7

509G8 493G7

(1) GIB MS (2) Review

(1) 1989SUM/ARM (2) 1996ARM/KIC

La+–F

141G8.1

589G34

Derived from IP in ref.

1996NIST

La+–Cl

120.4

503.6

Correlation

1999KAL/HEA

La+(H)x–H xZ0 1

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

–Br –I

La+(O)x–O xZ0

1

615

101.8 93.8

425.9 392.4

(1) (2) (3) (3) (4)

851G15 875G25 857 190 96G30

(1) Review (2) CID (3) Review

(1) 1989CHA/GIN (2) 2002JAC/KIN (3) 2006SCH

(4) CID

(4) 1992CLE/DAL

203.4G3.6 209G6 204.8 45.4 22.8G7.1

La+2–O

82.6

346

Derived

2000SCH/SCH(b)

La+–S

150G23

629G96

Derived from IP in ref.

1996NIST

La+–C –CH –CH2

(1) (1) (1) (2) (3) (2) (3)

427G33 523G33 444G21 414G6 401G7 231G15 217G15

(1) PD

(1) 1987HET/JAC

(2) GIB MS (3) Review

(2) 1989SUN/ARM (3) 1996ARM/KIC

–CH3

102G8 125G8 106G5 98.9G1.4 95.8G1.7 55.1G3.5 51.9G3.5

La+–C2H2

(1) 52G3 (2) 63G7

218G13 262G30

(1) PD (2) Review

(1) 1992RAN/FRE (2) 1996ARM/KIC

FeLa+–C2H2

O24

O100

PD

1987HUA/BUC

La+–C2H4

(1) R22 (2) 46

R92 192.5

(1) GIB MS (2) Review

(1) 1989SUN/ARM (2) 1998SCH/SCH

FeLa+–C2H6

O33

O138

PD

1987HUA/BUC (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

La+–C3H4

O71

O297

FT-MS

1987HUA/WIS

FeLa+–C3H4

O33

O138

PD

1987HUA/BUC

La+–C3H6 –C4H6

O31 O57

O130 O238

FT-MS

1987HUA/WIS

FeLa+–C3H8

O30

O126

PD

1987HUA/BUC

FeLa+–C4H6

O56

O234

PD

1987HUA/BUC

FeLa+–cyclo-C5H6

O50

O209

PD

1987HUA/BUC

La+–C6H6

58G8

243G34

Ion reactions

1988HUA/FRE

FeLa+–C6H6 FeLa+–CH3C6H5

R49.3 R48.9

R207 R204

Derived

1988HUA/FRE

La+–Si –SiH –SiH2 –SiH3

66.2G2.3 63.6G5.8 R55.1G1.6 46.1G6.5

277.0G9.6 GIB MS 266G24 R230.5G6.7 193G27

1995KIC/ARM(c)

Ce–Ce

(1) 57.8G5 (2) 60.2

242G21 251.7

(1) 1989CHA/GIN (2) 2000SHE/FAN

(1) MS (2) Spectroscopy

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

617

Ce–Ru –Os

118.0G2.9 130.3G4.8

494G12 524G20

MS

1989CHA/GIN

Ce–Rh –Ir

130.3G1.7 137.4G2.2

545G7 575G9

MS

1989CHA/GIN

Ce–Pd –Pt

76.2G5 131.5G1.2

319G21 550G5

MS

1989CHA/GIN

Ce–Au

77.0G4.3

322G18

MS

1989CHA/GIN

Ce–F

139G10

582G42

Review

1974GUR/KAR

Ce–Cl –Br –I

109.2 89.2 79.8

457.0 373.2 333.8

Correlation

1999KAL/HEA

Ce–O

(1) 189.8G4.1 (2) 189.1G4.6 (3) 188.8

794G17 791.2G19.3 790

Re-evaluated

(1) 1989CHA/GIN (2) 1991COC/NYU (3) 1994HAI

Ce–S –Se

(1) (2) (3) (2) (4)

569 477G20 494.5G14.6 385G20 189.4G12.6

MS

(1) 1969SMO/COP (2) 1970BER/COP (3) 1974NAG/SHI

–Te

136.0 114G4.7 118.2G3.5 92.0G4.7 45.3G3

(4) 1988KOY/YAM

Ce–N

124G5.0

519G21

MS

1971GIN(b)

Ce–C –C2 –C3 –C4 –C5

105.9G7 161G6 119G8 151G10 126G11

443G30 675G25 496G35 630G40 527G45

Derived

1989CHA/GIN

(continued)

7366—CHAPTER 13—3/2/2007—19:05—BSARAVANAN—15369—XML MODEL B – pp. 601–665

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Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ce–B

72.9G5

305G21

MS

1970GIN

Ce(polycr. surf.)–H2

45.9

192

Calorimetry

1986BOE/ZHA

Ce(111, surf.)–H2

18.5G2.3 (phys)

77.4G9.6

Review

1979TOY/SOM

Ce–O2

228G11.5

955G48

Re-evaluated

1991COC/NYU

CeCl3–CeCl3

54.1G3.8

226.4G15.7

MS

2002KAP/ROS

CeO2(111, surf.)–H2CO 35–36

146–151

Re-anal.

2001MAD/IDR

Ce+–Ce

49.5G10

207G42

Derived from IP in ref.

1996NIST

Ce+–Rh

101G23

423G96

Derived from IP in ref.

1996NIST

–Ir

127G23

530G96

Ce+–Pd

61G12.6

255G53

Derived from IP in ref.

1996NIST

112G23

467G96

66.3G8.1

278G34

Derived from IP in ref.

1996NIST

–Pt

Ce+–Au

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

619

Ce+(O)2–H

89G10

372G42

Derived

1996HEI/COR

Ce+–F

(1) 140G15 (2) 117G10

586G63 489G42

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

Ce+–Cl –Br –I

102.6 81.5 70.6

429.5 341.0 295.5

Correlation

1999KAL/HEA

(1) 202.9G3.6 (2) 197G17 (3) 204G3.6

849G15 824G71 852G15

(1) 1989CHA/GIN (2) 1996HEI/COR (3) 1996NIST

(4) 204 (2) 88G15 (4) 45.7

852 368G63 191

(1) Review (2) Derived (3) Derived from IP in ref. (4) Review

(4) 2006SCH

Ce+–O2

131.0

548

Review

2006SCH

Ce+–S

125G14

524G59

Derived from IP in ref.

1996NIST

Ce+–N

118G15

494G63

Derived from IP in ref.

1996NIST

Ce+–C

60.7G23

254G96

Derived from IP in ref.

1996NIST

Pr–Pr

(1) 31G7 (2) 30.9

130G29 129.1

(1) MS (2) Spectroscopy

(1) 1989CHA/GIN (2) 2000SHE/FAN

Pr–Au

74.3G6

311G25

MS

1989CHA/GIN

Ce+(O)x–O xZ0

1

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pr–F

139G11

582G46

Review

1974GUR/KAR

Pr–Cl –Br –I

101.2 82.3 73.2

423.5 344.5 306.2

Correlation

1999KAL/HEA

Pr–O

(1) 179.0G2.3 (2) 175.3G2.3 (3) 176.9

749G9.5 733.3G9.6 740

Re-evaluated

(1) 1989CHA/GIN (2) 1991COC/NYU (3) 1994HAI

Pr–O2

221.4G2.3

926.2G9.6

Re-evaluated

1991COC/NYU

Pr–S

117.7G1.1

492.5G4.6

MS

1973FEN/GOR

Pr–Se

(1) 100G4.8 (2) 106.7G5.5

418G20 446.4G23.0

MS

(1) 1970BER/COP (2) 1974NAG/SHI

Pr–Te

78G4.8

326G20

MS

1970BER/COP

Pr–C2 –C4

161G10 166G14

674G40 695G60

Derived

1989CHA/GIN

PrCl3–PrCl3

54.5G2.9

227.9G12.1

MS

2002KAP/ROS

Pr+–Au

76G19

317G81

Derived from IP in ref.

1996NIST

Pr+–F

133G15

557G63

Derived

1974GUR/KAR

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds Pr+–Cl –Br –I

Pr+(O)x–O xZ0

1

621

106.4 85.5 75.8

445.0 357.7 317.0

Correlation

1999KAL/HEA

(1) (2) (3) (3)

O749 796G15 802 212

(1) Ion beam (2) Review (3) Review

(1) 1988HAN/BEA (2) 1989CHA/GIN (3) 2006SCH

O179 190.2G3.6 191.7 50.7

Pr+–O2

124.3

520

Review

2006SCH

Nd–Nd

(1) 20G7 (2) 19.8

84G29 82.8

(1) MS (2) Spectroscopy

(1) 1989CHA/GIN (2) 2000SHE/FAN

Nd–Ag

!51

!213

MS

1974GUR/KAR

Nd–Au

70.3G7

294G29

MS

1989CHA/GIN

Nd(F)x–F xZ0 1 2

130.3G3 142.5G4.2 165G10

545.2G12.6 596G18 690G42

MS

1966ZMB/MAR

Nd–Cl –Br –I

100.1 81.2 72.1

418.7 339.7 301.5

Correlation

1999KAL/HEA

Nd–O

(1) 169.7G3.0 (2) 166.0G2.3 (3) 168

710G12.5 694.7G9.6 703

Re-evaluated

(1) 1989CHA/GIN (2) 1991COC/NYU (3) 1994HAI

Nd–O2

200.6G20.8

839G87

Re-evaluated

1991COC/NYU (continued)

7366—CHAPTER 13—3/2/2007—19:06—BSARAVANAN—15369—XML MODEL B – pp. 601–665

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Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Nd–S

112.7G3.5

471.5G14.6

MS

1969SMO/COP

Nd–Se

(1) 91.5G3.6 (2) 96.8G3.5 (3) 94.1

383G15 405.0G14.6 393.9

MS

(1) 1970BER/COP (2) 1974NAG/SHI (3) 1984GOR

Nd–Te

72.9G3.6

305G15

MS

1970BER/COP

Nd–C2 –C4

155G10 163G14

648G40 682G60

Derived

1989CHA/GIN

NdCl3–NdCl3

52.8G3.7

220.8G15.3

MS

2002KAP/ROS

Nd(h5-C5Me5)2– CH(SiMe3)2

56.6G2.5

236.8G10.5

Review

1994NOL

Nd+–Au

64G20

267G84

Derived from IP in ref.

1996NIST

Nd+–F

142.4G7.6

596G32

Derived from IP in ref.

1996NIST

Nd+–Cl –Br –I

105.5 84.3 74.1

441.4 352.9 309.8

Correlation

1999KAL/HEA

(1) 180.0G3.6 (2) 178.8 (2) 55.4

753G15 748 232

Review

(1) 1989CHA/GIN (2) 2006SCH

Nd+(O)x–O xZ0 1

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

623

Nd+–O2

116.2

486

Review

2006SCH

Pm–F

129G10

540G42

Review

1974GUR/KAR

Pm–Cl –Br –I

98.9 80.0 70.9

413.9 335.0 296.7

Correlation

1999KAL/HEA

Pm–O –S –Se –Te

161G13 101G13 81G13 61G13

674G63 423G63 339G63 255G63

Review

1974GUR/KAR

Pm+–F –Cl –Br –I

143.5 104.0 82.9 72.6

600.5 435.3 346.9 303.9

Correlation

1999KAL/HEA

Pm+(O)x–O xZ0 1

158.2 34.9

662 146

Review

2006SCH

Pm+–O2

75.0

314

Review

2006SCH

Sm–Sm

12.9G5

54G21

MS

1989CHA/GIN

Sm–Li

46.2G4.5

193.3G18.8

MS

1983NEU/ZMB

(h5-C5Me5)2Sm–H

(1) 52.4G2.0 (1) 56.8G3.0 (2) 54.2G3.0

219.2G8.4 237.7G12.6 226.8G12.6

(1) Calorimetry

(1) 1989NOL/STE

(2) Review

(2) 1994NOL

(1) 126.9G4.4

531G18

(1) MS

(1) 1967ZMB/MAR

Sm(F)x–F xZ0

(continued)

7366—CHAPTER 13—3/2/2007—19:06—BSARAVANAN—15369—XML MODEL B – pp. 601–665

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Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(2) 124.5G2.1 (3) R122.2 G2.4 (4) 135 (1) w138G10 (4) 135 (1) w160G10 (4) 139

520.9G8.8 R511G10

(2) CL (3) CL

(2) 1975DIC/ZAR (3) 1976YOK/MEN

565 w577G42 565 w669G42 582

(4) Derived

(4) 1981KLE/LAU

Sm–Cl

(1) R100.9G3 (2) 100.1

R422G13 418.7

(1) CL (2) Correlation

(1) 1976YOK/MEN (2) 1999KAL/HEA

Sm–Br –I

79.2 70.0

331.4 293.1

Correlation

1999KAL/HEA

(h5-C5Me5)2Sm–Cl –Br –I

97.1G3.0 83.6G1.5 69.4G2.4 72.7G2.9

406.3G12.6 349.8G6.3 290.4G10.0 304.2G12.1

Calorimetry

1989NOL/STE

Sm–O

(1) (2) (3) (4)

570.7G2.9 573G9.6 569.2G9.6 573

(1) (2) (3) (4)

(1) (2) (3) (4)

Sm–S

(1) 92.6G5 (2) 93

387.4G21 389

MS

(1) 1969SMO/COP (2) 1973FEN/GOR

Sm–Se

(1) (2) (3) (1) (2) (3)

314G40 331.0G14.6 289G42 230G40 272.4G14.6 201G42

MS

(1) 1970BER/COP (2) 1974NAG/SHI (3) 1974GUR/KAR

1 2

–Te

136.4G0.7 137.0G2.3 136.1G2.3 137

75.0G9.6 79.1G3.5 69G10 55.0G9.6 65.1G3.5 48G10

CL Re-evaluated Re-anal Review

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1975DIC/ZAR 1989CHA/GIN 1991COC/NYU 1994HAI

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

Sm–O2

149.9G2.3

625

627.1G9.6

Re-evaluated

1991COC/NYU

(h5-C5Me5)2Sm–OCH3 82.0 –SH3 73.4

343.1 307.1

Review

1992DRA/WON

(h5-C5Me5)2Sm– (h3-C3H5)

45.0G1.5

188.3G6.3

Calorimetry

1989NOL/STE

(h5-C5Me5)2Sm–SnC3H7

70.6G2.4 73.2G2.4

295.4G10.0 306.3G10.0

Calorimetry

1989NOL/STE

(h5-C5Me5)2Sm– N(CH3)2

48.2G1.8

201.7G7.5

Calorimetry

1989NOL/STE

(h5-C5Me5)2Sm–OtC4H9

(1) 82.4G3.5 (2) 81G1

344.8G14.6 338.9G4

(1) Calorimetry (2) Re-cal.

(1) 1989NOL/STE (2) 1995KIN/MAR

(h5-C5Me5)2Sm– OCHtC4H9

81.3G1.0

340.2G4.2

Calorimetry

1989NOL/STE

(h5-C5Me5)2Sm–CCPh 93.2

389.9

Calorimetry

1989NOL/STE

(h5-C5Me5)2Sm– CH2Si(CH3)3

49.0

205.0

Review

1992DRA/WON

(h5-C5Me5)2Sm– CH(SiMe3)2

(1) (1) (2) (2) (3)

192.5G7.5 201.7G6.3 201.7G7.5 196.6G6.3 196.6G8

(1) Calorimetry

(1) 1989NOL/STE

(2) Review

(2) 1994NOL

(3) Re-cal.

(3) 1995KIN/MAR

46.0G1.8 48.2G1.5 48.2G1.8 47.0G1.5 47G2

(continued)

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626

Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment) (h5-C5Me5)2Sm– SiH(SiMe3)2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

References

179.9G21

Calorimetry

1995KIN/MAR

(h5-C5Me5)2Sm–P(Et)2 32.6G2.0

136.4G8.4

Calorimetry

1989NOL/STE

Sm+–F

(1) 133.7G6.9

560G29

(1) 1996NIST

(2) 148.4

620.9

(1) Derived from IP in ref. (2) Correlation

104.1 82.1 71.5

435.4 343.3 299.1

Correlation

1999KAL/HEA

(1) 136.0G3.6 (2) 136.5 (2) 18.2

569G15 571 76

Review

(1) 1989CHA/GIN (2) 2006SCH

Sm+–O2

36.8

154

Review

2006SCH

Eu–Eu

(1) 7.9G4 (2) 10.8

33G17 45.2

(1) MS (2) Review

(1) 1989CHA/GIN (2) 2000FAN/CHE(c)

Eu–Li

64.1G3.0

268.1G12.6

MS

1983NEU/ZMB

Eu–Rh

56.9G8

238G34

MS

1989CHA/GIN

Eu–Ag –Au

30.4G3.1 58.6G2.9

127G13 245G12

MS

1989CHA/GIN

Sm+–Cl –Br –I

Sm+(O)x–O xZ0 1

43G5

kJ/mol

Methods (reference in parentheses)

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(2) 1999KAL/HEA

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

Eu(F)x–F xZ0

1 2

Eu–Cl –Br –I

627

(1) (2) (3) (1) (3) (1) (3)

126.1G4.1 130.5G2.1 130 w138G10 131 w160G10 119

528G17 546.0G8.8 544 w577G42 548 669G42 498

(1) MS (2) CL (3) Derived

(1) 1967ZMB/MAR (2) 1975DIC/ZAR (3) 1981KLE/LAU

(1) (2) (2) (2)

w78 96.9 78.1 68.9

w326 405.5 326.6 288.3

(1) Est. by exp. (2) Correlation

(1) 1972FIL/MOR (2) 1999KAL/HEA

(h5-C5Me5)2Eu–I

57.1G2.0

238.9G8.4

Review

1994NOL

Eu–O

(1) (2) (3) (4)

553.5G2.9 469G15 472.8G9.6 473

(1) (2) (3) (4)

(1) (2) (3) (4)

Eu–O2

94.5G23

396G96

Re-evaluated

1991COC/NYU

Eu–S

(1) 85.1G3.5 (2) 87.4G3.2

356.0G14.6 365.7G13.4

MS

(1) 1974NAG/SHI (2) 1978SMO/DRO

Eu–Se

(1) (2) (1) (2)

301G15 302.9G14.6 241G15 251.0G14.6

MS

(1) 1970BER/COP (2) 1974NAG/SHI

–Te

132.3G0.7 112.1G3.6 113.0G2.3 113.1

71.9G3.6 72.4G3.5 57.6G3.6 60.0G3.5

CL Re-evaluated Re-anal Review

1975DIC/ZAR 1989CHA/GIN 1991COC/NYU 1994HAI

Eu–C2

132G10

553G40

Re-evaluated

1989CHA/GIN

EuO–TiO2

131.7G6

551G25

MS

1985BAL/GIG (continued)

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628

Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment) Eu+–Ag

kcal/mol

kJ/mol

20.4G11.9

85G50

60G23

252G97

Eu+–F

(1) 118G15 (2) 129.7G6.9

Eu+–Cl –Br –I

Methods (reference in parentheses)

References

Derived from IP in ref.

1996NIST

494G63 543G29

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2)1996NIST

102.9 79.7 69.5

430.7 333.8 290.7

Correlation

1999KAL/HEA

(1) 93.9G3.6 (2) 98.5 (2) 2.4

393G15 412 10

Review

(1) 1989CHA/GIN (2) 2006SCH

Eu+–O2

K17.4

K73

Review

2006SCH

Eu+–S

61.3G7.6

257G32

Derived from IP in ref.

1996NIST

Gd–Gd

(1) 42G7 (2) 42.4 (3) 49.3G16.1

176G33 177.4 206.3G67.5

(1) MS (2) Review (3) Spectroscopy

(1) 1989CHA/GIN (2) 2000SHE/FAN (3) 2000CHE/FAN

Gd(polycs. surf.) –Gd

23.5 (phys)

98.3

FEM

1984CIS/MEL

Gd(polycs. surf.) –Gd

82

343

Review

1995SEE/ALL

–Au

Eu+(O)x–O xZ0 1

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

629

Gd(F)x–F xZ0 1 2

141.1G4 143G9 150G10

590G17 598G38 628G42

MS

1867ZMB/MAR

Gd–Cl –Br –I

107.8 88.9 79.8

451.0 372.0 333.8

Correlation

1999KAL/HEA

Gd–O

(1) 170.9G3.0 (2) 169.2G4.6 (3) 170.9

715G12.5 708G19 715

Re-evaluated

(1) 1989CHA/GIN (2) 1991COC/NYU (3) 1994HAI

Gd–S

(1) 125.4G3.5 (2) 125.9G2.5

524.7G14.6 526.8G10.5

MS

(1) 1969SMO/COP (2) 1978FRI/CAT

Gd–Se –Te

102.8G3.6 81.5G3.6

430G15 341G15

MS

1970BER/COP

Gd–C2

159G10

665G40

Re-evaluated

1989CHA/GIN

Gd(polycr. surf.)–H2

48.3

202

Calorimetry

1985SMU/CER

Gd–O2

196G16

820G68

Re-evaluated

1991COC/NYU

Gd+–F

(1) 136G15 (2) 140G8

569G63 585G34

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

Gd+–Cl –Br –I

96.6 75.5 66.0

404.3 315.8 276.3

Correlation

1999KAL/HEA

Gd+(O)x–O xZ0

(1) O179

O749

(1) CID

(1) 1988HAN/BEA (continued)

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630

Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol 175.9G3.6 173G6 178.5 60.0

kJ/mol

Methods (reference in parentheses)

References

1

(2) (3) (4) (4)

736G15 724G25 747 251

(2) Review (3) CID (4) Review

(2) 1989CHA/GIN (3) 2002JAC/KIN (4) 2006SCH

Gd+–O2

120.2

503

Review

2006SCH

Gd+–S

109G14

456G59

Derived from IP in ref.

1996NIST

Gd+–H2

120G5

502G21

Ion beam

1988HAN/BEA

Gd+–C6H6

O60

O251

Ion beam

1988HAN/BEA

Tb–Tb

(1) 31.5G6 (2) 33.2

132G25 138.8

(1) MS (2) Review

(1) 1989CHA/GIN (2) 2000FAN/CHE(c)

Tb–Cu –Au

45.7G4.3 68.1G8

191G18 285G33

MS

1989CHA/GIN

Tb–F

134G10

561G42

Review

1974GUR/KAR

Tb–Cl –Br –I

112.4 91.5 80.3

470.1 382.8 336.2

Correlation

1999KAL/HEA

Tb–O

(1) 166.6G5 (2) 168.3G4.6 (3) 165.9

697G21 704G19 694

Re-evaluated

(1) 1989CHA/GIN (2) 1991COC/NYU (3) 1994HAI

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

631

Tb–O2

205G25

859G106

Re-evaluated

1991COC/NYU

Tb–S

(1) 122.4G5 (2) 123G10

512.1G21 515G42

(1) Derived (2) Review

(1) 1969SMO/COP (2) 1974GUR/KAR

Tb–Se

(1) (2) (1) (2)

423G42 423G20 339G42 326G20

(1) Review (2) MS

(1) 1974GUR/KAR (2) 1970BER/COP

–Te

101G10 101G4.8 81G10 77.9G4.8

Tb–C2

156G11

652G45

Re-evaluated

1989CHA/GIN

Tb+–Cu

58.7G8.1

245G34

Derived from IP in ref.

1996NIST

(1) 172.6G3.6 (2) 177.8 (2) 47.1

722G15 744 197

Review

(1) 1989CHA/GIN (2) 2006SCH

Tb+–O2

106.8

447

Review

2006SCH

Dy–Dy

(1) 17G7 (2) 16.8

71G29 70.3

(1) MS (2) Review

(1) 1989CHA/GIN (2) 2000FAN/CHE(c)

Dy(polycs. surf.) –Dy

37.8 (phys)

185.2

FEM

1984CIS/MEL

Dy(polycs. surf.) –Dy

72

301.2

Review

1995SEE/ALL

Dy–Cu

34.4G4.3

144G18

MS

1989CHA/GIN

Dy–Ag

(1) 31.0G4.5 (2) 30.6G5.7

130G19 128G24

MS

(1) 1981HIL (2) 1989CHA/GIN

Tb+(O)x–O xZ0 1

(continued)

7366—CHAPTER 13—3/2/2007—19:06—BSARAVANAN—15369—XML MODEL B – pp. 601–665

632

Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Dy–Au

61.9G5.7

259G24

MS

1989CHA/GIN

Dy–F

127

531

MS

1966ZMB/MAR(b)

Dy–Cl

93.8

392.4

Correlation

1999KAL/HEA

Dy(Br)x–Br xZ0 1 2

81.1G2.5 96.1G3.2 106.0G3.8

339.3G10.5 402.1G13.4 443.5G15.9

MS

2004HIL/LAU

Dy(I)x–I xZ0 1 2

64.3G2 80.1G2.8 82.8G3.5

269.0G8.4 335.1G11.7 346.4G14.6

MS

2004HIL/LAU

Dy–O

(1) 146G5 (2) 143G6.9 (3) 147.0

611G21 598G29 615

Re-evaluated

(1) 1989CHA/GIN (2) 1991COC/NYU (3) 1994HAI

Dy–S

(1) 98.1G5 (2) 99G10

410.5G21 414G42

(1) Derived (2) Review

(1) 1969SMO/VOP (2) 1974GUR/KAR

Dy–Se –Te

77.0G4.8 56.0G4.8

322G20 234G20

MS

1970BER/COP

Dy–C2 –C4

135G11 129G14

565G44 538G60

Derived

1989CHA/GIN

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

633

Dy(polycr. surf.) –H2

48.8

204

Calorimetry

1986BOE/ZHA

DyCu(polycr. surf.) –H2 DyCu6(polycr. surf.) –H2

39.9

167

Calorimetry

1993BAS/CER

w21.5

w90

Dy–O2

168G28

704G116

Re-evaluated

1991COC/NYU

Dy(polycr. surf.)–O2

228.5

956

Calorimetry

1988CER/KOV

Dy(polycr., surf.) –CO

86.8

363

Calorimetry

1987CER/PIE

DyCu(polycr. surf.)–CO

77–80

322–335

Calorimetry

1993BAS/CER

DyCu6(polycr. surf.)–CO

74.6

312

Calorimetry

1993BAS/CER

Dy(polycr. surf.)–CH4 –C2H2 –C3H6

O65 100 w155

O272 418 w648

Calorimetry

1990CER/SMU

DyCl3–DyCl3

61.5G4.1

257.3G17.1

MS

2002KAP/ROS

DyBr3–DyBr3

52.8G1.6

220.8G6.6

MS

1995HIP/MIL

(DyI3)x–DyI3 xZ1 2

46.2G1.3 47.1G3.4

193.3G5.6 197.0G14.2

MS

2004 HIL/MIL (continued)

7366—CHAPTER 13—3/2/2007—19:06—BSARAVANAN—15369—XML MODEL B – pp. 601–665

634

Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

DyBr3–NaBr DyI3–NaI

57.5G5 50G10

240.6G21 209G42

MS

2005HIL/LAU

NaDyBr4–NaDyI4 NaDyBr4–NaDyBr2I2

4.9G5 1.9G5

21G21 8G21

MS

2005HIL/LAU

Dy+–Cu

46.8G10

196G42

Derived from IP in ref.

1996NIST

Dy+–F

(1) 121G15 (2) 128G5.7

506G50 535G24

Derived

(1) 1974GUR/KAR (2) 1999KAL/HEA

Dy+–Cl –Br –I

97.5 77.5 66.9

407.9 324.2 279.9

Correlation

1999KAL/HEA

(1) 142.7G3.6 (2) 140.5 (2) 25.3

597G15 588 106

Review

(1) 1989CHA/GIN (2) 2006SCH

Dy+–O2

47.8

200

Review

2006SCH

Ho–Ho

(1) 20.6G7.2 (2) 16.8

86G30 70.3

(1) MS (2) Review

(1) 1989CHA/GIN (2) 2000FAN/CHE(c)

Ho–Cu –Ag –Au

34.4G4.5 29.6G4.5 63.8G8.4

144G19 124G19 267G35

MS

1989CHA/GIN

Dy+(O)x–O xZ0 1

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

635

Ho–F

129

540

MS

1966ZMB/MAR(b)

Ho–Cl –Br –I

97.8 76.9 65.8

409.1 321.8 275.1

Correlation

1999KAL/HEA

Ho–O

(1) 147.5G2.3 (2) 145.3G6.9 (3) 144.8

617G9.6 608G29 606

Re-evaluated

(1) 1989CHA/GIN (2) 1991COC/NYU (3) 1994HAI

Ho–O2

189G25

791G106

Re-evaluated

1991COC/NYU

Ho–S

102.4G3.5

428.4G14.6

MS

1969SMO/COP

Ho–Se –Te

79.6G3.6 %61.9G3.6

333G15 %259G15

MS

1970BER/COP

Ho–C2 –C4

135G10 142G14

565G40 596G60

Derived

1989CHA/GIN

Ho+–Ho

21G23

88G96

Derived from IP in ref.

1996NIST

Ho+–Cu

51G8.4

214G35

Derived from IP in ref.

1996NIST

37G15 60G14

155G61 250G60

Ho+–F

(1) 129G15 (2) 130G12

540G63 542G50

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

Ho+–Cl –Br –I

98.1 76.6 64.6

410.3 320.6 270.4

Correlation

1999KAL/HEA

–Ag –Au

(continued)

7366—CHAPTER 13—3/2/2007—19:07—BSARAVANAN—15369—XML MODEL B – pp. 601–665

636

Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment) Ho+(O)x–O xZ0

kcal/mol 143.9G3.6 131.7G6 140.1 46.1

kJ/mol

Methods (reference in parentheses)

References

1

(1) (2) (3) (3)

602G15 551G25 586 193

(1) Review (2) CID (3) Review

(1) 1989CHA/GIN (2) 2002JAC/KIN (3) 2006SCH

Ho+–O2

68.1

285

Review

2006SCH

Er–Er

17.9G7

75G29

MS

1989CHA/GIN

Er(1000, surf.)–Er

35 (phys)

146

FEM

1986KOZ/CIS

Er(1000, surf.)–Er

76

318

Review

1995SEE/ALL

Er(0110, surf.)–Er

26 (phys)

109

FEM

1986KOZ/CIS

Er–F

135G4

565G17

MS

1966ZMB/MAR(b)

Er–Cl –Br –I

107.2 86.3 75.5

448.6 361.3 315.8

Correlation

1999KAL/HEA

Er–O

(1) 146.0G2.3 (2) 146.3G6.9 (3) 144.8

611G10 612G29 606

Re-evaluated

(1) 1989CHA/GIN (2) 1991COC/NYU (3) 1994HAI

Er–S

100G5

418G21

Derived

1969SMO/COP

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

637

Er–Se –Te

78G4.8 57.0G4.8

326G20 238G20

MS

1970BER/COP

Er–C2

137G15

573G63

Derived

1989CHA/GIN

Er(polycr. surf.)–H2

48.8

204

Calorimetry

1986BOE/ZHA

Er–O2

175G27

733G116

Re-evaluated

1991COC/NYU

ErCl3–ErCl3

50.9G3.6

213G15

Derived from DfH0 in ref.

2002POG/MOT

Er+–F

(1) 128G15 (2) 130.6G8.1

536G63 546G34

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

Er+–Cl –Br –I

97.2 75.5 64.9

406.7 315.8 271.6

Correlation

1999KAL/HEA

(1) 139.3G3.6 (2) 141.0 (2) 27.2

583G15 590 114

Review

(1) 1989CHA/GIN (2) 2006SCH

ErC–O2

50.2

210

Review

2006SCH

ErClK 4 –ErCl3

54G7.2

226G40

Derived from DfH0 in ref.

2002POG/MOT

Tm–Tm

12.9G4

54G17

MS

1989CHA/GIN

Er+(O)x–O xZ0 1

(continued)

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638

Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Tm–Li

66.0G3.5

276.1G14.6

MS

1983NEU/ZMB

Tm(F)x–F xZ0 1 2

122 134 148

510 561 619

MS

1981KLE/LAU

Tm–Cl –Br –I

90.3 71.5 62.3

378.0 299.1 260.8

Correlation

1999KAL/HEA

Tm–O

(1) 122.4G2.3 (2) 119.9G4.6 (3) 122.8

512G9.6 502G19 514

Re-evaluated

(1) 1989CHA/GIN (2) 1991COC/NYU (3) 1994HAI

Tm–S

87.9G5

368G21

Derived

1969SMO/COP

Tm–Se –Te

65.5G9.6 43.5G9.6

274G40 182G40

MS

1970BER/COP

Tm–C2

125G11

524G44

Derived

1989CHA/GIN

Tm(polycr. surf.)–H2

46.1

193

Calorimetry

1986BOE/ZHA

Tm–O2

138G32

579G135

Re-evaluated

1991COC/NYU

Tm+–F –Cl

128.4G3.7 97.5

537G16 407.9

Correlation

1999KAL/HEA

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

–Br –I

639

74.6 63.8

312.2 266.8

(1) 115.2G3.6 (2) 113.0 (2) 4.3

482G15 473 18

Review

(1) 1989CHA/GIN (2) 2006SCH

Tm+–O2

K0.5

K2

Review

2006SCH

Yb–Yb

(1) 5G4 (2) 3.9

21G17 16.3

(1) MS (2) Review

(1) 1989CHA/GIN (2) 2000FAN/CHE(c)

Yb–Li

34.3G3.0

143.5G12.6

MS

1983NEU/ZMB

Yb–H

(1) 38.0G9 (2) 43.7G0.5

159G38 183.1G2.0

(1) Review (2) MS

(1) 1990SIM/BEA (2) 2005BRU/TER

Yb–F

(1) 113 (2) R123.7 G2.3

473 (1) Spectroscopy R517.6G9.6 (2) CL

(1) 1975BAR/CHO (2) 1976YOK/MEN

Yb–Cl

(1) w77 (2) 89.5

w322 374.5

(1) Est. by exp. (2) Correlation

(1) 1972FIL/MOR (2) 1999KAL/HEA

Yb–Br –I

70.6 61.5

295.4 257.3

Correlation

1999KAL/HEA

(h5-C5Me5)2Yb–I

61.2G1.5

256.1G6.3

Review

1994NOL

Yb–O

(1) (2) (3) (4)

397.9G6.3 405G21 405G29 401

(1) (2) (3) (4)

(1) (2) (3) (4)

Tm+(O)x–O xZ0 1

95.1G1.5 96.8G5 96.9G6.9 95.8

CL Re-evaluated Re-ana. Review

1976YOK/MEN 1989CHA/GIN 1991COC/NYU 1994HAI (continued)

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640

Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(5) 92.7G2.4

387.7G10

(5) MS

(5) 2005BRU/TER

Yb–OH

77.0G2.9, at 0 K

322G12

MS

2005BRU/TER

Yb–O2

88G32

367G135

Re-evaluated

1991COC/NYU

Yb–S

(1) %38.8 (2) 40

%162.3 167

(1) Derived (2) Review

(1) 1969SMO/COP (2) 1974GUR/KAR

Yb+–Yb

57G23

238G96

Derived from IP in ref.

1996NIST

Yb+–F –Cl –Br –I

133.2G3.4 95.5 73.5 62.6

557.5G14.4 399.6 307.4 262.0

Correlation

1999KAL/HEA

(1) 89.9G3.6 (2) 92.0 (2) K13.6

376G15 385 K57

Review

(1) 1989CHA/GIN (2) 2006SCH

Yb+–O2

K39.7

K166

Review

2006SCH

Lu–Lu

(1) 33.9G8 (2) 67G42

142G33 280G174

(1) MS (2) Spectroscopy

(1) 1989CHA/GIN (2) 2000FAN/CHE(c)

Lu–Pt

96.1G8

402G34

MS

1989CHA/GIN

Yb+(O)x–O xZ0 1

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References

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

641

Lu–Au

79.3G4.5

332G19

MS

1989CHA/GIN

Lu–D

72.2

302

Spectroscopy

1994RAJ/DHU

Lu–F

(1) 79.7 (2) 96.8G4.5

333.5 404G19

Spectroscopy

(1) 1982ISH/VAR (2) 2005COO/KRU

Lu–Cl

(1) 90.9 (2) 77.8G0.5

380.4 325.7G2

(1) Correlation (2) Spectroscopy

(1) 1999KAL/HEA (2) 2005COO/KRU

Lu–Br –I

72.1 62.9

301.5 263.2

Correlation

1999KAL/HEA

Lu–O

(1) 159.4G2.3 (2) 161G4.6 (3) 159.9

667G9.6 675G19 669

Re-evaluated

(1) 1989CHA/GIN (2) 1991COC/NYU (3) 1994HAI

Lu–S

(1) 121.1G3.5 (2) 121.5G3.2

506.7G14.6 508.4G14.4

MS

(1) 1969SMO/COP (2) 1979FRA/HAR

Lu–Se –Te

99.9G3.6 77.7G3.6

418G15 325G15

MS

1970BER/COP

Lu–C2 –C4

155G11 153G14

648G48 640G60

Derived

1989CHA/GIN

Lu(polycr. surf.)–H2

43.0

180

Calorimetry

1986BOE/ZHA

Lu–O2

191G25

801G106

Re-evaluated

1991COC/NYU

Lu(h5-C5Me5)2– CH(SiMe3)2

66.7G2.5

279.1G10.5

Review

1994NOL (continued)

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642

Comprehensive Handbook of Chemical Bond Energies

Table 13.3 (continued) BDEs of La– and LaC–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Lu+–F –Cl –Br –I

90.1 43.2 20.6 9.7

376.8 180.6 86.1 40.7

Correlation

1999KAL/HEA

Lu+(H)x–H xZ0 1

48.7G3.7 49.6G5.8

204G15 207G24

GIB MS

1989SUN/ARM

Lu+–2H

(1) 98.2G4.4 (2) 94.2G4.4

411G18 394G18

(1) GIB MS (2) Review

(1) 1989SUN/ARM (2) 1996ARM/KIC

Lu+–CH2

(1) (2) (1) (2)

R240G5 O230G6 190G20 176G20

(1) GIB MS (2) Review

(1) 1989SUN/ARM (2) 1996ARM/KIC

(1) 125.2G3.6 (2) 131.5 (2) 17.9

524G15 550 75

Review

(1) 1989CHA/GIN (2) 2006SCH

Lu+–O2

31.5

132

Review

2006SCH

Lu+–Si –SiH2

25.6G3.2 22.6G2.3

107G13 95G10

GIB MS

1995KIC/ARM(c)

–CH3

Lu+(O)x–O xZ0 1

R57.4G1.2 55.0G1.4 45.4G4.8 42.1G4.8

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

643

13.4 AcKand AcC–X bonds Table 13.4.1 BDEs of Ac– and AcD–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ac–O

189.8

794

Est. by exp.

2003GIB

Th–Th

%69G8

%289G33

MS

1969GIN

Th–Ru

141.4G10

592G42

MS

1974GIN

Th–Rh

122.6G5

513G21

MS

1978GIN/GUP

Th–Ir

137.3G10

574G42

MS

1973GIN

Th–Pt

131.6G10

551G42

MS

1973GIN

(h5-C5Me5)2Th(R)–H, RZOCH[C(CH3)3]2

(1) 92.1G1, in sol. (1) 84.9G1.2, in gas (2) 93.0G1.4

385.3G4

(1) Calorimetry

(1) 1986BRU/STE

389G6

(2) Review

(2) 1990SIM/BEA

385.3G4

(1) Calorimetry

(1) 1986BRU/STE

355.2G5.0

(1) 92.1G1, (h5-C5Me5)2Th(R)–H, RZO-2,6[C(CH3)3] – in sol. C6H3 (1) 84.9G1.2, in gas (2) 91.8G1.4

384G6

(2) Review

(2) 1990SIM/BEA

(h5-C5H4SiMe3)3 Th–H

274G6 277G6

Calorimetry

(1) 1993JEM/GOF (2) 1994GOF/JEM

(1) 65.5G1.4 (2) 66.2G1.4

355.2G5.0

(continued)

7366—CHAPTER 13—3/2/2007—19:08—BSARAVANAN—15369—XML MODEL B – pp. 601–665

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Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(C9H6SiMe3)3Th–H –D

63.1G2 66.0G1.2

264G8 276G5

Calorimetry

1993JEM/GOF

Th(F)x–F xZ0

(1) 158.4G4

663G16.7

(1) 1985HIL/GUV

(2) 155.8 (1) 168.1G4 (2) 167.8 (1) 156.2G4 (2) 156.1 (1) 157.7G4 (2) 159.2 (3) 154

652 703G16.7 702 654G16.7 653 660G16.7 666 644

(1) Der. from DfH0 in ref. (2) MS

(2) 1989LAU/BRI

(3) Derived

(3) 1986BRU/STE

OTh–F

142.0

594

Derived

1989LAU/BRI

Th(Cl)x–Cl xZ0

(1) 111.3G4

466G16.7

(1) 1985HIL/GUV

(2) 116.9 (1) 126.0G4 (2) 130.3 (1) 120.2G4 (2) 121.2 (1) 133.0G4 (2) 120.5

489 527G16.7 545 503G16.7 507 557G16.7 504

(1) Der. from DfH0 in ref. (2) Derived

(1) 105.3G6

441G25

(2) 87.0

364

1 2 3

1 2 3

Th(Br)x–Br xZ0

(1) Der. from DfH0 in ref. (2) MS

(2) 1990LAU/HIL

(1) 1985HIL/GUV (2) 1990HIL/LAU

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

1

(1) 115G8 (2) 104.9 (1) 103G8 (2) 114.0 (1) 109.6G7 (2) 121.9

481G34 439 431G34 477 459G29 510

Th(I)x–I xZ0

86.3G6

361G25

1 2 3

94G8 85G8 92.1G7

393G24 356G34 385G29

(1) 205.2G3.9 (2) 213 (3) 209.6 (4) 163.5G8.8

(F)Th–O

2 3

645

Derived from DfH0 in ref.

1985HIL/GUV

858.6G16.3 891 877 684G37

(1) MS (2) Derived (3) Derived (4) Derived

(1) 1974NEU/ZMB (2) 1994HAI (3) 2003GIB/HAI (4) 2002SAN/MAR

194.3

813

Derived

1989LAU/BRI

(h5-C5H4SiMe3)3 Th–O

93.7G2.6

392G11

Calorimetry

1994GOF/JEM

88.7G5.7

371G24

Th–N –P

(1) 138G8 (2) 89G7

577G33 372G29

MS

(1) 1968GIN (2) 1969GIN

Th–B

71G8

297G33

MS

1969GIN

Th–C –C2 –C3

108.3G4.1 148.4G4.3 130.7G4.5

453G17 621G18 547G19

MS

1980GUP/GIN

ThC2–C2 ThC3–C2

167.8G6.9 150.1G6.9

702G29 628G29

MS

1980GUP/GIN

Th(O)x–O xZ0

1

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(h5-C5Me5)2 Th(OR)H–CO RZCH(t-Bu)2

82.5G2

345G8

Review

1990SIM/BEA

(h5-C5Me5)2 Th(OR)H–CO RZ2,6-(t-Bu)2C6H3

83.9G2.4

351G10

Review

1990SIM/BEA

(h5-C5H5)3Th–CH3

(1) 89.6G1.1, in sol. (1) 82.7G1.1, in gas (2) 89.6G2.2

374.9G4.6

(1) Calorimetry

(1) 1985SON/MOR

375G9

(2) Review

(2) 1990SIM/BEA

(h5-C5H4SiMe3)3 Th–CH3

46.8G1.7

196G7

Calorimetry

1994GOF/JEN

(h5-C5Me5)2Th(CH3)– CH3

(1) 81.2G0.8, in sol. (1) 77.2G1.1, in gas (2) 81.0G1.2

339.7G3.3

(1) Calorimetry

(1) 1983BRU/MAR

339G5

(2) Review

(2) 1990SIM/BEA

349.8G3.8

(1) Calorimetry

(1) 1983BRU/MAR

(h5-C5Me5)2Th (O-tC4H9)–CH3

(C9H7)3Th–CH3

346.0G4.6

323.0G4.6

(1) 83.6G0.9, in sol. (1) 79.3G1.2, in gas (2) 83.4G1.4

349G6

(2) Review

(2) 1990SIM/BEA

88.7G1.4

371G6

Calorimetry

1989BET/GOF

331.8G5.0

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

647

(1-C2H5-C9H6)3 Th–CH3

87.2G1.2

365G5

Calorimetry

1989BET/GOF

(h5-C5Me5)2 Th(Cl)–C2H5

(1) 72.2G1.8, in sol. (1) 68.3G2.0, in gas (2) 74.8G1.9

302.1G7.5

(1) Calorimetry

(1) 1983BRU/MAR

313G8

(2) Review

(2)1990SIM/BEA

(h5-C5Me5)2 Th(C2H5)– (1) 73.5G1.6, C2H5 in sol. (1) 70.4G2.0, in gas (2) 76.0G1.9

307.5G6.7

(1) Calorimetry

(1) 1983BRU/MAR

318G8

(2) Review

(2) 1990SIM/BEA

(h5-C5Me5)2 Th(O-tC4H9)–C2H5

(1) 76.3G1.6, in sol. (1) 72.9G2.0, in gas (2) 78.9G1.9

319.2G6.7

(1) Calorimetry

(1) 1983BRU/MAR

330G8

(2) Review

(2) 1990SIM/BEA

(1) 81.8G2.6, in sol. (1) 77.3G2.7, in gas (2) 83.7G3.6

342.3G10.9

(1) Calorimetry

(1) 1985SON/MOR

350G15

(2) Review

(2) 1990SIM/BEA

(C9H7)3Th–i-C3H7

85.3G1.9

357G8

Calorimetry

1989BET/GOF

(h5-C5Me5)2Th(Cl)– N(CH3)2

89.2G2.0, in sol. 90.8G2.4, in gas

373.2G8.4

Calorimetry

1983BRU/MAR

(1) 71.6G1.0, in sol. (1) 71.6G1.7, in gas (2) 73.4G2.2

299.6G4.2

(1) Calorimetry

(1) 1983BRU/MAR

(2) Review

(2) 1990SIM/BEA

(h5-C5H5)3Th–i-C3H7

(h5-C5Me5)2Th (n-C4H4)–nC4H9

285.8G8.4

294.6G8.4

305.0G8.4

323.4G11.3

379.9G10.0

299.6G7.1 307G9

(continued)

7366—CHAPTER 13—3/2/2007—19:08—BSARAVANAN—15369—XML MODEL B – pp. 601–665

648

Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment) (h5-C5Me5)2Th (O-tC4H9)–nC4H9

(h5-C5Me5)2Th(R)– n-C4H9, RZOCH[C(CH3)3]2

(h5-C5H5)3Th– CH2C(CH3)3

(h5-C5Me5)2 Th(CH2C(CH3)3)– CH2C(CH3)3

(h5-C5Me5)2Th (O-tC4H9)– CH2C(CH3)3

(h5-C5H5)3Th– CH2Si(CH3)3

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 73.6G3.4, in sol. (1) 73.9G3.7, in gas (2) 75.5G3.6

307.9G14.2

(1) 81.3G3.1, in sol. (1) 81.5G3.1, in gas (2) 82.9G3.6

(1) 79.6G2.8, in sol. (1) 77.9G3.0, in gas (2) 79.6G3.6

(1) 72.3G3.8, in sol. (1) 72.2G3.9, in gas (2) 72.2G4.1

(1) 76.9G3.7, in sol. (1) 77.0G3.9, in gas (2) 76.7G4.1

(1) 87.9G3.6, in sol.

Methods (reference in parentheses)

References

(1) Calorimetry

(1) 1983BRU/MAR

316G15

(2) Review

(2) 1990SIM/BEA

340.2G13

(1) Calorimetry

(1) 1986BRU/STE

347G15

(2) Review

(2) 1990SIM/BEA

333.0G11.7

(1) Calorimetry

(1) 1985SON/MOR

333G15

(2) Review

(2) 1990SIM/BEA

302.5G15.9

(1) Calorimetry

(1) 1983BRU/MAR

302G17

(2) Review

(2) 1990SIM/BEA

321.7G15.5

(1) Calorimetry

(1) 1983BRU/MAR

321G17

(2) Review

(2) 1990SIM/BEA

367.8G15.1

(1) Calorimetry

(1) 1985SON/MOR

309.2G15.5

341.0G13

325.9G12.6

302.1G16.3

322.2G16.3

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

649

(1) 86.1G3.6, in gas (2) 88.2G2.9

360.2G15.1 369G12

(2) Review

(2) 1990SIM/BEA

(1) 80.0G3.1, in sol. (1) 80.3G3.4, in gas (2) 80.1G1.7

334.7G13.0

(1) Calorimetry

(1) 1983BRU/MAR

335G7

(2) Review

(2) 1990SIM/BEA

(1) 82.2G3.1, in sol. (1) 82.7G3.3, in gas (2) 82.5G1.7

343.9G13.0

(1) Calorimetry

(1) 1983BRU/MAR

345G7

(2) Review

(2) 1990SIM/BEA

(C9H7)3Th– CH2Si(CH3)3

94.9G1.7

397G7

Calorimetry

1989BET/GOF

(h5-C5Me5)2Th(Cl)– NMeSiMe3

95.5G2.1, in sol. 100.2G2.5, in gas

399.6G8.8

Calorimetry

1983BRU/MAR

(1) 89.2G2.2, in sol. (1) 90.5G2.3, in gas (2) 89.4G2.4

373.2G9.2

(1) Calorimetry

(1) 1986BRU/STE

374G10

(2) Review

(2) 1990SIM/BEA

(1) 88.9G2.4, in sol. (1) 90.3G2.5, in gas (2) 88.9G2.4

372.0G10.0

(1) Calorimetry

(1) 1983BRU/MAR

(2) Review

(2) 1990SIM/BEW

(h5-C5Me5)2 Th(CH2SiMe3)– CH2Si(CH3)3

(h5-C5Me5)2 Th(O-tC4H9)– CH2Si(CH3)3

(h5-C5Me5)2Th(Cl)– C6H5

(h5-C5Me5)2 Th(C6H5)–C6H5

336.0G14.2

346.0G13.8

419.2G10.5

378.7G9.6

377.8G10.5 372G10

(continued)

7366—CHAPTER 13—3/2/2007—19:08—BSARAVANAN—15369—XML MODEL B – pp. 601–665

650

Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment) (h5-C5Me5)2 Th(O-tC4H9)–C6H5

(h5-C5H5)3Th– CH2C6H5

(h5-C5Me5)2Th(Cl)– CH2C6H5

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) 92.4G2.1, in sol. (1) 95.1G2.3, in gas (2) 92.4G2.2

(1) 75.3G2.2, in sol. (1) 77.9G2.2, in gas (2) 75.3G2.9

kJ/mol 386.6G8.8

Methods (reference in parentheses)

References

(1) Calorimetry

(1) 1983BRU/MAR

387G9

(2) Review

(2) 1990SIM/BEW

315.1G9.2

(1) Calorimetry

(1) 1985SON/MOR

315G12

(2) Review

(2) 1990SIM/BEA

285.3G5.9

(1) Calorimetry

(1) 1983BRU/MAR

397.9G9.6

325.9G9.2

(1) 68.2G1.4, in sol. (1) 71.5G1.9, in gas (2) 68.1G1.7

285G7

(2) Review

(2) 1990SIM/BEW

(C9H7)3Th–CH2C6H5

81.7G2.2

342G9

Calorimetry

1989BET/GOF

Th+–Ru

120G16

504G67

Derived from IP in ref.

1996NIST

93G46

388G193

(1) 159G9

664G36

(1) 1985HIL/GUR

(2) 163G7

682G29

(1) Der from DfH0 in ref. (2) Der. from IP in ref.

(1) 168G11 (1) 151G11 (1) 6.6G8.4

701G47 630G47 28G35

–Pt

Th+(F)x–F xZ0

1 2 3

299.2G7.9

(2) 1996NIST

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds Th+(Cl)x–Cl xZ0

(1) 159G8

664G34

(2) 119G7

499G29

(1) 121G11 (1) 102G11 (1) 37G8

506G47 427G47 155G34

(1) 207G5

866G21

(2) R179.6 (3) 202.0 (1) 103.5G5 (2) R84.7 (3) 114.5

R751 845 433G21 R354 479

ThC 2 –O

R179.5

Th+–O2

1 2 3

Th+(O)x–O xZ0

(1) Der. from DfH0 in ref. (2) Der. from IP in ref.

651

(1) 1985HIL/GUR (2) 1996NIST

(1) 1985HIL/GUR

(1) Der. from DfH0 in ref. (2)Derived (3) Review

(2) 2002SAN/MAR (3) 2006SCH

R751

Derived

2005GIB/HAI

198.6

831

Review

2006SCH

(1) 188.4G4.1 (2) 189.3 (1) 184.6G4.1

788G17 792 772G17

(1) AP (2) Review

(1) 1986KLI/WAR (2) 1994HAI

Pa+(F)3–F

O95.6

O400

Derived

2002GIB/HAI

Pa+(O)x–O xZ0 1

w191 R184

w800 R770

Derived

2002GIB/HAI

U–U

53G5

222G21

Review

1974GUR/KAR

1

Pa(O)x–O xZ0 1

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

U–Rh

124.0G4

519G17

MS

1978GIN/GUP

U–Au

(1) 73.8G7 (2) 76G7

309G29 318G29

(1) MS (2) Review

(1) 1967GIN/BLU (2) 1974GUR/KAR

U–Al

78G7

326G29

MS

1967GIN/BLU

U–B U–B2

77G8 227G10

322G33 950G42

MS

1970GIN

(h5-C5H4tBu)3U–H

59.7G1.4

249.7G5.7

Calorimetry

1992JEM/GOF

(h5-C5H4SiMe3)3U–H

(1) 60.2G1.2 (2) 60.6G1.2

251.7G5.1 253.7G5.1

Calorimetry

(1) 1992JEM/GOF (2) 1944GOF/JEM

(h5-C5Me5)2 U(OSi(tBu) (Me)2)–H

(1) 82.4G0.7, in sol.

344.8G2.9

(1) Calorimetry

(1) 1986BRU/STE

(1) 76.4G1.1, in gas (2) 81.7G1.2

319.7G4.6 342G5

(2) Review

(2) 1990SIM/BEA

(1) 157G6 (2) 157G6 (3) 156.4G4

657G25 657G25 654G16.7

(1) 1979WAR/KLE (2) 1984GOR/SMI (3) 1985HIL/GUV

(4) 154.9 (1) 136 (2) 136.5G8.1 (3) 136G5.5

648 569 571G34 569G23

(1) Derived (2) Derived (2) Der. from DfH0 in ref. (4) Derived

U(F)x–F xZ0

1

(4) 1992HIL/LAU(c)

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

2

3

4

5

U(O)Fx–F xZ0 1 2 3

U(Cl)x–Cl xZ0

1

2

3

4

(4) 135.0 (1) 149 (2) 143.4G6 (3) 145G5 (4) 147.9 (1) 148 (2) 148.4G4.3 (3) 148.1G3 (4) 147.0 (1) 102 (2) 90.6G4.5 (3) 99.9G3.5 (4) 98.0 (1) 65 (2) 75.0G2.9 (3) 69.2G3.5

565 623 600G25 607G21 619 619 621G18 620G12.6 615 426 379G19 418G14.6 410 272 314G12 290G14.6

159G24

665G100

156G34 113G34 84.8G25

653G142 473G142 355G105

(1) 108G2 (2) 105.4G3.6

452G8 441G15

(3) 104.9 (1) 117G2 (2) 115G4.5 (3) 115.0 (1) 117G2 (2) 116G4.5 (3) 115.9 (1) 101G2 (2) 100.4G4.5 (3) 100.4 (4) 86 (1) 50G2 (2) 50G4.5 (3) 50.0

439 490G8 481G19 481 490G8 485G19 485 423G8 420G19 420 360 209G8 209G19 209

653

Derived from DfH0 in ref.

1985HIL/GUV

(1) MS (2) Der. from DfH0 in ref. (3) Derived

(1) 1984LAU/HIL (2) 1985HIL/GUV (3) 1992HIL/LAU(c)

(4) Derived

(4) 1986BRU/STE

(continued)

7366—CHAPTER 13—3/2/2007—19:09—BSARAVANAN—15369—XML MODEL B – pp. 601–665

654

Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

101

422.6

Review

1992LEA/MAR

(1) 90.1G3.6

377G15

(1) 1985HIL/GUV

(2) 90.1 (1) 103.5G4.5 (2) 104.0 (1) 102.1G4.5 (2) 102.8 (1) 82.6G3.5 (2) 83.2 (3) 77 (2) 39.7

377 433G19 435 427G19 430 346G15 348 322 166

(1) Der. from DfH0 in ref. (2) Derived

(2) 1992HIL/LAU(c)

(3) Derived

(3) 1986BRU/STE

71.4G6.5

299G27

Derived from DfH0 in ref.

1985HIL/GUV

83G8.5 83G8.5 65.7G6

347G36 347G36 275G25

(h5-C5Me5)3U–I

62.6G0.2

262G1

Calorimetry

1990BET/GOF

(h5-C5H4tBu)3U–I

58.9G1.3

246.3G5.3

Calorimetry

1992JEM/GOF

(h5-C5H4SiMe3)3U–I

(1) 62.4G1.4 (2) 63.5G1.0

261.1G5.9 265.6G4.3

Calorimetry

(1) 1988SCH/SEY (2) 1992JEM/GOF

(C9H7)3U–I

63.8G0.8

266.8G3.2

Calorimetry

1990BET/GOF

[HB(3,5-Me2Pz)3] U(Cl)2–Cl PzZpyrazolyl

U(Br)x–Br xZ0

1 2 3

4

U(I)x–I xZ0 1 2 3

7366—CHAPTER 13—3/2/2007—19:09—BSARAVANAN—15369—XML MODEL B – pp. 601–665

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

U(O)x–O xZ0

(1) 180.5G3 (2) 185.0 (3) 188.4

755G13 774 788

(4) 180.4 (5) 180G18.2 (6) 181.5 (6) 136.7

755 753G76 759.3 572.1

(h5-C5H4SiMe3)3U–O

75.8G3.6 76.2G2.4

(h5-C5H4tBu)3U–O

U(O)x–O2 xZ0 1

655

(1) Derived (2) Derived (3) Der. from data in ref. (4) Derived (5) Derived (6) Derived

(4) 2003GIB (5) 2002SAN/MAR (6) 2005CAP/COL

317G15 319G10

Calorimetry

1994GOF/JEM

73.4G2.2

307G9

Calorimetry

1994GOF/JEM

242.6 198.8

1015.0 831.7

Derived

2005CAP/COL

U–S

(1) 134G2.3 (2) 126.3G2.5

561G9.6 528.4G10.5

MS

(1) 1966CAT/RAU (2) 1975STE/CAT

U–N

127G5

531G21

MS

1967GIN

U–P

70G5

293G21

Review

1974GUR/KAR

U–C –C2 –C3

108.7G3.6 158.9G3.8 134.0G5.0

455G15 665G16 561G21

MS

1979GUP/GIN

UC3–C2 UC2–C3

156.3G9.3 131.0G8.1

654G39 548G34

MS

1979GUP/GIN

1 2

(1) 1983PED/MAR (2) 1994HAI (3) 1994KAL/MCC

(continued)

7366—CHAPTER 13—3/2/2007—19:09—BSARAVANAN—15369—XML MODEL B – pp. 601–665

656

Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment) (h5-C5H4SiMe3)3 U–CO –CH3

(h5-C5Me5)2U(CH3)– CH3

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 10.3G0.2

43.1G0.8

(1) Calorimetry

(1) 1988SCH/SEY

(1) 44.8G1.1 (2) 44.2G0.5

187.4G4.6 185G2

(2) Review

(2) 1994LEA/SIM

(1) 71.8G3.3, in sol. (1) 67.8G3.5, in gas (2) 71.7G2.6

300.4G13.8

(1) Calorimetry

(1) 1986BRU/STE

300G11

(2) Review

(2) 1990SIM/BEA

312.1G6.7

(1) Calorimetry

(1) 1986BRU/STE

283.7G14.6

(h5-C5Me5)2U(Cl)–CH3 (1) 74.6G1.6, in sol. (1) 70.1G1.7, in gas (2) 74.6G1.9

312G8

(2) Review

(2) 1990SIM/BEA

(h5-C5Me5)2U(R)–CH3 RZOSi(tBu)Me2

293.3G7.1

(1) 76.0G1.2, (1) 72.4G1.4, in sol. in gas (2) 75.8G1.4

318.0G5.0 302.9G5.4

(1) Calorimetry

(1) 1986BRU/STE

317G6

(2) Review

(2) 1990SIM/BEA

(C9H7)3U–CH3

46.9G1.6

196.3G6.6

Calorimetry

1990BET/GOF

(1-C2H5-C9H6)3 U–CH3

44.7G1.4

187G6

Calorimetry

2001LEA/MAR

(h5-Me3SiC5H4)3 U–C2H3

(1) 48.5G2.2

202.9

(1) Calorimetry

(1) 1988SCH/SEY

(2) 53.3G2.4

223G10

(2) Review

(2) 1990SIM/BEA

7366—CHAPTER 13—3/2/2007—19:09—BSARAVANAN—15369—XML MODEL B – pp. 601–665

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

657

(C9H7)3U–OCH2CF3

71.9G2.2

301G9

Calorimetry

1990BET/GOF

(L)3U–SC2H5 LZ(h5-C5H4tBu) (h5-C5H4SiMe3) (C9H6SiMe3)

60.2G2 63.6G2.2 37.8G2

252G8 266G9 158G8

Calorimetry

1994JEM/GOF

(h5-C5Me5)2U (c-C3H5)–c-C3H5

88.0G5

368G21

Calorimetry

1986BRU/STE

(h5-C5H4Me3Si)3 U–nC4H9

(1) 28.9G1.7

120.9G7.1

(1) Calorimetry

(1) 1988SCH/SEY

(2) 36.3G1.9

152G8

(2) Review

(2) 1990SIM/BEA

[HB(3,5-Me2Pz)3] U(Cl)2–O-tC4H9, PzZpyrazolyl

110.1G1.2

460.5G5.0

Calorimetry

1992LEA/MAR

(h5-C5H4Me3Si)3 U–S-tC4H9

37.8G2

158G8

Calorimetry

1994JEM/GOF

(h5-C5Me5) 2U(CH2SiMe3)– CH2Si(CH3)3

(1) 73.3G3.1, in sol.

306.7G13.0

(1) Calorimetry

(1) 1986BRU/STE

(1) 73.3G3.3, in gas (2) 73.4G1.9

306.7G13.8 307G8

(2) Review

(2) 1990SIM/BEA

(1) 39.3G2.3

164.4G9.2

(1) Calorimetry

(1) 1988SCH/SEY

(2) 40.2G1.9

168G8

(2) Review

(2) 1990SIM/BEA

79.8G2.4

334G10

Calorimetry

1992LEA/MAR

(h5-C5H4SiMe3)3 U–CH2Si(CH3)3

[HB(3,5-Me2Pz)3] U(Cl)2– –N(SiMe3)2

(continued)

7366—CHAPTER 13—3/2/2007—19:09—BSARAVANAN—15369—XML MODEL B – pp. 601–665

658

Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

–CH(SiMe3)2, PzZpyrazolyl

70.5G2.6

295G11

(h5-C5H5)3U– Si(Si(CH3)3)3

37G3

154.8G12.6

Calorimetry

1995KIN/MAR

(Cl)2U(dmpz)– –OCMe2CH2COMe, dmpz Z3, 5-dimethyl pyrazol-1-yl

115.7G2.1

484.2G8.6

Calorimetry

1994LEA/SIM

(Cl)2U(dmpz)–dmpz, dmpzZ3, 5-dimethyl pyrazol-1-yl

93.9G3.8

393G16

Calorimetry

1994LEA/SIM

(Cl)2U(dmpz)–THF, dmpzZ3, 5-dimethyl pyrazol-1-yl THFZ tetrahydrofuran

5.1G0.7

21.5G2.9

Calorimetry

1994LEA/SIM

[HB(3,5-Me2Pz)3] U(Cl)2–c-C5H5, PzZpyrazolyl

86.5G2.9

362G12

Calorimetry

1992LEA/MAR

(h5-C5Me5)2U(Cl)– C6H5

(1) 85.5G2.6, in sol. (1) 86.7G2.6, in gas (2) 85.6G2.6

357.7G10.9

(1) Calorimetry

(1) 1986BRU/STE

(2) Review

(2) 1990SIM/BEA

362.8G10.9 358G11

7366—CHAPTER 13—3/2/2007—19:09—BSARAVANAN—15369—XML MODEL B – pp. 601–665

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

659

(h5-C5H4SiMe3)3 U–CCC6H5

86.7

362.8

Calorimetry

1988SCH/SEY

(h5-C5Me5)2 U(CH2C6H5)– CH2C6H5

(1) 58.3G2.1, in sol.

243.9G8.8

(1) Calorimetry

(1) 1986BRU/STE

(1) 61.8G2.7, in gas (2) 58.3G1.9

258.6G11.3 244G8

(2) Review

(2) 1990SIM/BEA

(1) 63.0G2.7, in sol. (1) 66.1G2.8, in gas (2) 62.9G2.9

263.6G11.3

(1) Calorimetry

(1) 1986BRU/STE

276.6G11.7 263G12

(2) Review

(2) 1990SIM/BEA

(h5-C5H4SiMe3)3 U–CH2C6H5

(1) 25.6G3.1

107.1G13.0

(1) Calorimetry

(1) 1988SCH/SEY

(2) 35.6G1.9

149G8

(2) Review

(2) 1990SIM/BEA

(L)U–L, LZh8-1,3,5,7cyclooctatetraene

45.4G6.5

190G27

MS

1977BED

(h5-C5H5)3U–SiPh3

(1) 37.3G4.2 (2) 35G4

156.1G17.6 146.4G16.7

(1) Calorimetry (2) Re-cal.

(1) 1991NOL/POR (2) 1995KIN/MAR

(h5-C5H5)3U–GePh3 –SnPh3

38.9G4.5 37.2G4.0

162.8G18.8 155.6G16.7

Calorimetry

1991NOL/POR

(h5-C5H5)3U –Fe(CO)2(h5-C5H5) –Ru(CO)2(h5-C5H5)

30.9G3.0 40.4G4.0

129.3G12.6 169.0G16.7

Calorimetry

1991NOL/POR

9.8G0.2

41.0G0.8

Calorimetry

1988SCH/SEY

(h5-C5Me5)2U(Cl)– CH2C6H5

(h5-C5H4SiMe3)3 U–THF THFZtetrahydrofuran

(continued)

7366—CHAPTER 13—3/2/2007—19:09—BSARAVANAN—15369—XML MODEL B – pp. 601–665

660

Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(C9H7)3U–THF, THFZtetrahydrofuran

17.0G1.2

71.3G5.2

Calorimetry

1991JEM/GOF

U+–H

67.9G2

284G8

Ion beam

1977ARM/HOD

U+–D

67.7G2.3

283.4G9.6

CID

1977ARM/HOD

(1) 125G27 (2) 160.4G7.1

523G113 671G30

(1) 1981ARM/BEA (2) 1985HIL/GUR

(3) 159.7G6.9 (2) 132G10.6 (3) 131.9G10.5 (2) 125G9 (3) 125G9 (2) 92G4.5 (3) 91.1G4.5 (2) 85.3G4.5 (3) 58.1G4.1 (2) 60G4 (3) 6.2G2.6

668G29 552G44 552G44 522G38 523G38 385G19 381G19 357G19 243G17 251G17 26G11

(1) CID (2) Der. from DfH0 in ref. (3) Review

w24

w100

Derived

2004JAC/GIB

(1) O84G1 (2) 103G8

O352G4 431G34

(1) CID (2) Der. from DfH0 in ref.

(1) 1981ARM/BEA (2) 1985HIL/GUR

(2) 103G11 (2) 77G11 (2) 85G8.5 (2) 26G8.5

431G46 322G46 356G36 109G36

U+(F)x–F xZ0

1 2 3 4 5

U+(OH)–F

U+(Cl)x–Cl xZ0

1 2 3 4

(3) 2004JAC/GIB

7366—CHAPTER 13—3/2/2007—19:09—BSARAVANAN—15369—XML MODEL B – pp. 601–665

BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds U+(Br)x–Br xZ0

661

Derived from DfH0 in ref.

1985HIL/GUR

199G75

Derived from DfH0 in ref.

1985HIL/GUR

(1) 184G7 (2) R179.6 (3) 181

770G29 R752 757

(1) 1980ARM/BEA (2) 2002SAN/MAR (3) 2003HAN/KAL

(4) 190.2 (5) 182.4 (1) 178G9 (2) 184.5G13 (3) R151 (5) 138.9 (6) 182.6G5.7

796 763 745G38 772G56 R632 581 764G24

(1) CID (2) Derived (3) Der. from IP in ref. (4) Derived (5) Review

(7) 31

130

UC 2 –O

R151.1 165G14

U+–O2

82.5G7

345G29

1 2 3

96.7G10 69.7G11 50.7G11

405G42 292G46 212G46

U+(I)3–I

47.5G18

U+(O)x–O xZ0

1

(4) 2004JAC/GIB (5) 2006SCH

(6) 1985HIL/GUV

(6) Der. from DfH0 in ref. (7) Derived

(7) 2001GIB

R632 690G60

Derived

2005GIB/HAI

240.9

1008

Review

2006SCH

U+(F)x–OH xZ1 2

O115.2G6.9 O108.3G9.1

O482G29 O453G38

Derived

2004JAC/GIB

U+–S

124G5

518G29

Derived from IP in ref.

1996NIST

2

(continued)

7366—CHAPTER 13—3/2/2007—19:09—BSARAVANAN—15369—XML MODEL B – pp. 601–665

662

Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

U+–N

(1) 109.2G4.6 (2) w116

457G19 w485

CID

(1) 1981ARM/BEA (2) 1995HEI/SCH

U+(O)–N

w120

w502

CID

1995HEI/SCH

U+–P

45G10

186G42

Derived from IP in ref.

1996NIST

72G23

300G96

Np(F)x–F xZ0

102.8G12

430G50

Derived from DfH0 in ref.

1985HIL/GUR

1 2 3 4

145G18.5 140G18.5 148G17 153G14.5

607G77 586G77 619G71 640G61

(1) 175.9 (2) 176.9 (3) 174.7 (4) 122.4G20.6

736 740 731 512G86

Derived

(1) 1994HAI (2) 2001GIB (3) 2003GIB (4) 2002SAN/MAR

Np+(F)x–F xZ0 1 2 3

174G24 105G22 131G14 57G10

730G100 440G90 550G60 240G40

Derived

2002GIB/HAI

Np+(O)x–O xZ0

(1) 184.8G10

773G42

(1) Der. from DfH0 in ref.

(1) 1988LIA/BAR

–C

Np(O)x–O xZ0

1

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

(2) w189

w790

(3) R179.6 (4) 179.6 (3) R119.1 (3) 138.6G16.7 (4) 138.9

R752 752 R498 580G70 581

NpC 2 –O

R119.0 127G7

Np+–O2

1

Pu(F)x–F xZ0

1

2

3 4 5

Pu(O)x–O xZ0

1

Pu–O2

663

(2) Ion reactions (3) Derived (4) Review

(2) 2001GIB (3) 2002SAN/MAR (4) 2006SCH

R498 530G30

Derived

2005GIB/HAI

200.5

839

Review

2006SCH

(1) 143.9 (2) 114.7G6.5

602 480G27

(1) 1986KLE/WAR (2) 1985HIL/GUV

(3) 128.7G7 (1) 128.7 (2) 137.2G7 (3) 135G8 (1) 141.1 (2) 149.8G6 (3) 147G10 (1) 156.1 (3) 113G5 (1) 136.1 (3) 108G12 (1) 58.8 (3) 53G2

538G29 538 574G29 565G33 590 627G25 615G42 653 473G21 569 452G50 246 222G8

(1) Derived (2) Der. from DfH0 in ref. (3) MS

(1) 168.0 (2) 159 (3) 167.3 (4) 158.0 (5) 156.8 (2) 143 (5) 143.7

703 666 700 661 656.1 598 601.1

Derived

(1) 1994HAI (2) 1999CAP/COL (3) 2001GIB (4) 2003GIB (5) 2005CAP/COL

182.2

762.2

Derived

2005CAP/COL

(3) 1988KLE

(continued)

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664

Comprehensive Handbook of Chemical Bond Energies

Table 13.4.1 (continued) BDEs of Ac– and AcC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pu–N

112G15

469G63

Review

1974GUR/KAR

Pu+(O)x–O xZ0

(2) 163.2G13

683G55

(1) 1985HIL/GUV

(2) 156.5

655

(3) 147.7 (3) R151 (1) 60.6G18 (3) 124.3G5 (3) R119.1

618G22 R632 254G75 520G20 R498

(1) Der. from DfH0 in ref. (2) Ion reactions (3) Derived

(3) 2002SAN/MAR

R84.6 110G12

R354 460G50

Derived

2005GIB/HAI

134.3G12

562G50

Derived from DfH0 in ref.

1985HIL/GUV

126G17 124G26

527G71 519G96

(1) 131.5 (2) 132.2G8.6 (2) 123.8G11.2

550 553G36 518G47

(1) Review (2) Derived

(1) 1985HIL/GUR (2) 2002SAN/MAR

Am+(O)x–O xZ0 1

133.8G7.2 93.2G9.6

560G30 390G40

Derived

2002SAN/MAR

AmC 2 –O

R84.6

R354

Derived

2005GIB/HAI

1

PuC 2 –O

Pu+(F)x–F xZ0 1 2

Am(O)x–O xZ0 1

(2) 2001GIB/HAI

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BDEs of Sc(ScC)–, Y(YC)–, La(LaC)–, and Ac(AcC)–X Bonds

665

Am+–Cl

96G12 w78

400G50 w327

Est.

2004TIL/NAL

Cm–O

175

732

Equilibrium

1970SMI/PET

Bk–O

143

598

Est. by exp.

2003GIB

Bk+–O

145.8

610

Ion reactions

2001GIB/HAI

Cf–O

119

498

Est by exp.

2003GIB

Es–O

(1) 143 (2) 110

598 460

Est. by exp.

(1) 1994HAI (2) 2003GIB

Es+–O

112G14.3

470G60

Est. by exp.

2003GIB/HAI

Fm–O Md–O No–O Lr–O

106 100 64 159

443 418 268 665

Est. by exp.

2003GIB

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chapter fourteen

BDEs of Ti(Ti G )–, Zr(ZrC )–, and Hf(HfC)–X bonds

14.1 Ti–, TiC–, and TiK–X bonds 14.1.1 Ti–X bonds Table 14.1.1 BDEs of Ti–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Ti–Ti

(1) (2) (3) (4) (5)

Ti–Zr

32.8G5 30.8 29.3G3.9 33.2 28.1

kJ/mol

Methods (reference in parentheses) MS Review Review Review Spectrometry

References

137.2G21 129 122.6G16.4 138.8 117.6

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

1969KAN/LIN 1979MIE/GIN 1986MOR 1996SMI/YAT 2004HIM/BIH

51.2G0.1

214.3G0.1

Spectrometry

1995LAN/MOR

Ti–V

48.58G0.02

203.24G0.10

Spectrometry

1992SPA/MOR(b)

Ti–Nb

72.2G0.1

302.0G0.1

Spectrometry

1995LAN/MOR

Ti–Co

56.26G0.02

235.37G0.10

Spectrometry

1992SPA/MOR(b)

(continued)

667

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Comprehensive Handbook of Chemical Bond Energies

Table 14.1.1 (continued) BDEs of Ti–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ti–Rh

93.4G3.5

390.8G14.6

Review

1986MOR

Ti–Ir

100.9G3.1

422G13

MS

1989PEL/GIN

Ti–Pt

95.0G2.5

397.5G10.6

Review

1986MOR

Ti–Al

63.0

263.4

MS

1979HUB/HER

Ti–H

(1) 47.1 (2) 48.9G2.1

197 204.6G8.8

(1) Review (2) GIB MS

(1) 1990SIM/BEA (2) 1991CHE/CLE

136G8 160G8 155G5 109G5

569G33 669G33 649G21 456G21

MS

1967ZMB/MAR(c)

(1) 96.9G2.5 (2) 105.3

405.4G10.5 441

(1) MS (2) Derived from DfH0 in ref.

(1) 1996HIL(b) (2) 1996NIST

(1) (2) (1) (2) (1) (2)

507.5G10.5 513 422.2G10.5 423 388.3G10.5 345

Derived

1988DIA/SIM

Ti(F)x–F xZ0 1 2 3

Ti(Cl)x–Cl xZ0

1 2 3

Ti(Cl)x(h5-C5H5)2–Cl xZ0 1

121.3G2.5 122.6 100.9G2.5 101.2 92.8G2.5 82.5

112.6 93.2

471 390

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BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X Bonds

669

Ti(Cl)x(h5-C5Me5)2–Cl xZ0 1

115G5 90.8G4.8

481G21 380G20

Calorimetry

1988DIA/SAL

Ti(Br)x–Br xZ0 1 2 3

89.1 120.3 73.5 68.6

373 503 308 287

Derived from DfH0 in ref.

1996NIST

Ti(I)x–I xZ0 1 2 3

73.2 95.7 56.7 55.9

306 400 237 234

Derived from DfH0 in ref.

1996NIST

TiCptt2 –I, CpttZh5-1,3-di-tertbutylcyclo-pentadienyl

40.6

170

Calorimetry

1999KIN/BEL

Ti(h5-C5Me5)2–I

52.3

219

Calorimetry

1999KIN/BEL

(1) Review (2) Derived from DfH0 in ref. (3) Mol. beam (4) Spectroscopy

(1) 1990SIM/BEA (2) 1996NIST

Ti(O)x–O xZ0

1

(1) 160.6G2.2 672G9 (2) 159.8 669 (3) 159.3G1.4 666.5G5.6 (4) 160.9G3.7 673.3G15.4 (2) 145.6 609

(3) 1997NAU/HED (4) 2000RED/AHA

Ti–S

99.9G0.7

418G3

MS

1979PEL/VIS

Ti–Se –Te

91G10 69G4

381G42 289G17

Review

1974GUR/KAR

Ti–N

113.8G8

476G33

MS

1970STE/KOH

(continued)

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Table 14.1.1 (continued) BDEs of Ti–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ti–B

65G15

272G63

Review

1974GUR/KAR

Ti–C –C2

101.1G7.2 137

423G30 573

Review

1990SIM/BEA

TiO2–EuO

131.7G6

551G25

MS

1985BAL/GIG

TiN(100, surf.)–TiN

78.4G6.9

328.0G28.9

STM

2000KOD/PET

Ti(polycr. surf.)–H2

24.9–39.0

104–163

Calorimetry

1966WED/STR

Ti(polycr. surf.)–O2

(1) 235.7 (2) 218

986 912

(1) Calorimetry (2) Review

(1) 1960BRE/HAY (2) 1982RAO/KAM

TiO2(110, surf.)–O2

4.3 (phys)

18

TPD

2006DOH/KIM

TiO2(110, surf.)–N2

6.7 (phys)

28

TPD

2006DOH/KIM

TiO2(110, surf.)–NO

8.4

35.1

Adsorption

2000SOR/RUS

Ti(CO)x(h5-C5H5)2–CO xZ0 1

41.6 40.6

174 170

Derived

1988DIA/SIM

TiO2(surf.)–CO

w14.3

w60

Calorimetry

1998BOL/CER

TiO2(110, surf.)–CO

10 (phys)

42

TPD

2006DOH/KIM

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BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X Bonds

671

Ti2O(110, surf.)CO–CO

9.9

41.4

TPD

1995LIN/LU

TiO2(110, surf.)/Au–CO

2.7G0.7

11.4G2.8

TPD

1999BON/PAR

Ti(polycr. surf.)–CO

153

640

Calorimetry

1965BRE/HAY

Ti(polycr. surf.)–CO2

(1) 163 (2) 191

682 799

(1) Review (2) Calorimetry

(1) 1964HAY/TRA (2) 1965BRE/HAY

TiO2(110, surf.)–H2O

(1) 17 (2) 17–19 (3) 14–24

71 71–79 68–100

(1) TPD (2) TPD (3) Mol. Beam

(1) 1994HUG/GAM (2) 1996HEN (3) 1998BRI/DIE

TiO2(001, surf.)–NH3

22

92

TDP

2004WIL/IDR

Ti–CH3

42G7

174G29

GIB MS

1990ARM

Ti(Cl)(h5-C5H5)2–CH3

(1) 70.0G2.6 (2) 66.0

293G11 276

(1) Calorimetry (2) Derived

(1) 1987CAL/DIA (2) 1988DIA/SIM

(1) (1) (2) (3)

309 287 274G5 297.9G5.9

(1) Derived

(1) 1988DIA/SIM

(2) Calorimetry (3) Review

(2) 1987CAL/DIA (3) 1994NOL

(1) 71.7G6.9 (1) 64.8 (2) 67.2G1.9

300G29 271G21 281G8

(1) Calorimetry

(1) 1988DIA/SAL

(2) Re-cal.

(2) 1990SIM/BEA

Ti(h5-C5Me5)2–CH3

71.7G6.9

300G29

Calorimetry

1988DIA/SAL

TiO2(001, surf)–H2CO

40

167.4

Re-anal.

2001MAD/IDR

Ti(CH3)x(h5-C5H5)2–CH3 xZ0 1

Ti(CH3)x(h5-C5Me5)2–CH3 xZ0 1

73.9 68.6 65.5G1.2 71.2G1.4

(continued)

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Table 14.1.1 (continued) BDEs of Ti–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ti(Cl)(h5-C5H5)2–C2H5

35.9

150

Review

1990SIM/BEA

Ti(polysc.)–C3H7F

20.5

85.8

Kinetics

1971HAR/SUM

Ti(polysc.)–C2H5Cl –C3H7Cl

22.3 23.5

93.2 98.3

Kinetics

1971HAR/SUM

Ti(polysc. surf.)–C3H7Br

27.5

115.1

Kinetics

1971HAR/SUM

Ti(polysc. surf.)–C3H7I

29.5

123.4

Kinetics

1971HAR/SUM

Ti(Cl)(h5-C5H5)2–C6H5

(1) 69.3G3.1 (2) 69.8

290G13 292

(1) Calorimetry (2) Derived

(1) 1987CAL/DIA (2) 1988DIA/SIM

(1) (1) (2) (3)

372 290 287G9 331.8G10

(1) Derived

(1) 1988DIA/SIM

(2) Calorimetry (3) Review

(2) 1987CAL/DIA (3) 1994NOL

(1) 87.5G7.4 366G31 (1) 64.3G66.9 269G28 (2) 66.9G4.5 280G19

(1) Calorimetry

(1) 1988DIA/SAL

(2) Re-cal.

(2) 1990SIM/BEA

(1) 40.6G3 (2) 22.1 (2) 73.8

Derived

(1) 1999KUR/TAK (2) 2001PAN/RAO

Ti(C6H5)x(h5-C5H5)2–C6H5 xZ0 1

Ti(C6H5)x(h5-C5Me5)2–C6H5 xZ0 1

Ti(C6H6)x–C6H6 xZ0 1

88.9 69.3 68.6G2.2 79.3G2.4

169.8G12.5 92.6 308.7

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BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X Bonds

673

Ti(R)(h5-C5H5)2–L LZ3-CH3C6H4 -4-CH3C6H4 -4-CF3C6H4 -4-CH3O–C6H4 (h5-C5H5)Fe(h5-C5H4)

71.5G2.4 71.0G2.4 71.0G2.4 72.9G2.2 66.4G2.6

299G10 297G10 297G10 305G9 278G11

Calorimetry

1987CAL/DIA

Cl4Ti–CH3CHCHCHO –CH3CHCHC(O)OCH3 –CH3C(CH3)CHCHO –CH3CHCHCN

14.0G0.6 13.6G0.7 17.9G0.3 11.5G0.3

58.6G2.5 56.9G2.9 74.9G1.3 48.1G1.3

Calorimetry

1982CHI/MUL

w26 w26

w109 w109

Combined

2005HUA/HAN

Methods (reference in parentheses)

References

Ti–O bonds C5H5 C5H5

Ti Cl

XZH OMe

Me O

Me

N

X

Me Me

14.1.2 TiC– and TiK–X bonds Table 14.1.2 BDEs of TiD– and TiL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) TiC–Ti

TiC(Ti)x–Ti xZ1 2 3 4 5 6 7 8 9 10

kcal/mol

kJ/mol

(1) 56.2 (2) 54.7 (3) 36.9

234.9 229 154.2

(1) CID (2) Review (3) Est. by exp.

(1) 1994RUS/HEI (2) 2001ARM (3) 2004HUB/HIM

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1)

230 338 340 354 400 278 346 335 344 406

(1) Review

(1) 2001ARM

55.0 80.8 81.3 84.6 95.6 66.4 82.7 80.1 82.2 97.0

(continued)

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674

Comprehensive Handbook of Chemical Bond Energies

Table 14.1.2 (continued) BDEs of TiC– and TiK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) 11 12 13 14 15 16 17 18 19 20 N

kcal/mol (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2) (3)

112.3 76.7 95.6 86.0 82.2 76.0 107.6 97.8 94.4 98.0 112.5 w100.6

kJ/mol 470 321 400 360 344 318 450 409 395 410 471 w421

Methods (reference in parentheses)

References

(2) Review (3) Extrapolate

(2) 1994ARM/HAL (3) This volume

TiCO–Mn TiC–OMn

40.65G0.03 111.1G2.5

170.09G0.12 465.0G10.6

PD

2001FU/RUS

TiC–Fe

(1) 60G6 (2) O49

251G25 O205

(1) PD (2) Ion reactions

1987HET/FRE

TiC–Pt

20G23

82G96

Derived from IP in ref.

1996NIST

TiC–H

54.2G2.5

226.6G10.6

GIB MS

1988ELK/ARM

TiC–F

R109

R456

Ion reactions

1978ALL/RID

TiC(Cl)x–Cl xZ0 1 2 3

102 90 78 38

426.8 376.6 326.4 159.0

Derived

1999KNE/LER

TiC(H2)x–H2 xZ0

(1) 7.5G0.5

31.4G2.1

Equilibrium

(1) 1997BUS/MAI

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BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X Bonds

675

(2) (1) (2) (1) (2) (1) (2) (1) (2) (1) (2)

7.9 9.7G0.6 9.8 9.3G0.7 9.3 8.5G0.4 8.7 8.2G0.4 8.5 8.7G0.4 8.3

33.1 40.6G2.5 41.0 38.9G2.9 38.9 35.6G1.7 36.4 34.3G1.7 35.6 36.4G1.7 34.7

(1) (2) (3) (2)

94.4G5.5 121G4 114.2G1.3 93.4G3.5

395G23 506G17 478G5 391G15

GIB MS

(1) 1991CLE/ELK (2) 1988SUN/ARM (3) 1989SUN/ARM

(1) 57.5G2.8 (2) 51.1G0.7 (2) 62G6

241G12 213.8G3 259G25

GIB MS

(1) 1988SUN/ARM (2) 1989SUN/ARM

16.8G0.6 17.4G0.6 6.6G1.5 9.8G0.8 5.1G0.7

70.3G2.5 72.8G2.5 27.6G6.3 41.0G3.3 21.3G2.9

Equilibrium

1999KOP/PER

H(CH3)TiC(CH4)x–CH4 xZ2 9.8G0.8 3 5.1G0.7

41.0G3.3 21.3G2.9

Equilibrium

1995KOP/KEM

(CH2)TiC(CH4)x–CH4 xZ0 1 2

O24 19.2G1.0 7.2G0.5

O100 80.3G4.2 30.1G2.1

Equilibrium

1995KOP/KEM

(1) (2) (1) (1)

253G19 213G13 334G24 R119

(1) GIB MS (2) Re-examined

(1) 1989SUN/ARM (2) 1997GID/KOP

1 2 3 4 5

TiC–C –CH –CH2

TiC(CH3)x–CH3 xZ0 1

TiC(CH4)x–CH4 xZ0 1 2 3 4

TiC–C2H2 –C2H3 –C2H4

60.4G4.6 51G3 79.9G5.8 R28.5

(2) 1999BOW/KEM

(continued)

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676

Comprehensive Handbook of Chemical Bond Energies

Table 14.1.2 (continued) BDEs of TiC– and TiK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

–C2H5 –(CH3)2

TiC–C3H4 –C3H6 –C4H6

TiC(C6H6)x–C6H6 xZ0 1

kcal/mol (3) (4) (1) (5)

34.8G2.5 31 49.5G1.6 112.8G6.0

kJ/mol

Methods (reference in parentheses)

References

146G11 129.7 207G7 472G25

(3) GIB MS (4) Review

(3) 1998SIE/JAR (4) 1998SCH/SCH

(5) Review

(5) 1996ARM/KIC

(1) 60G3 (2) 34.5G3 (3) O28.1

251G13 144G13 O118

(1) GIB MS (2) KERD (3) Ion reactions

(1) 1989SUN/ARM (2) 1998KOP/BOW (3) 1976ALL/RID

(1) (2) (1) (2)

259G9 213 253G18 272

(1) CID (2) FT-ICR

(1) 1995MEY/KHA (2) 2002GAP/DUN

61.9G2.2 51 60.5G4.3 65

ClTiC(C6H6)x–C6H6 xZ0 1

63 39

264 163

FT-ICR

2002GAP/DUN

Cl2TiC(C6H6)x–C6H6 xZ0 1

63 !30

264 !126

FT-ICR

2002GAP/DUN

BrTiC(C6H6)x–C6H6 xZ0 1

63 39

264 163

FT-ICR

2002GAP/DUN

Br2TiC(C6H6)x–C6H6 xZ0 1

60 !30

251 !126

FT-ICR

2002GAP/DUN

ITiC(C6H6)x–C6H6 xZ0 1

62 40

259 167

FT-ICR

2002GAP/DUN

7366—CHAPTER 14—6/2/2007—13:24—CRCPAG—15370—XML MODEL B – pp. 667–687

BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X Bonds I2TiC(C6H6)x–C6H6 xZ0 1

677

57 !30

238 !126

FT-ICR

2002GAP/DUN

(1) 151–257 (2) 159.4G1.6 (3) 80.7G2.3

632–1075 667G7 337.7G9.6

(1) ICR (2) CID (3) CID

(1) 1981KAP/STA (2) 1991CLE/ELK (3) 1999HAR/DIE

TiC(S)–O

76.8G3.5

321.3G14.5

CID

2000KRE/SCH

TiC–O2

122.8

514

Review

2006SCH

TiC–OH

(1) 113.0 (2) 111.1G2.8

473 465G12

Ion reactions

(1) 1989MAG/DAV(b) (2) 1993CLE/ARI

28.1G1.4 27.0G0.9 23.9G0.9 20.8G1.2 16.6G0.9 17.8G0.7 12.5G1.6

117.7G5.8 112.9G3.9 100.0G3.9 86.9G4.8 69.5G3.9 74.3G2.9 52.1G6.8

CID

1996MEY/ARM

(1) (2) (2) (2) (2) (3)

159.0 157.7G5.9 136.4G5.0 66.9G6.7 83.3G7.5 w44

CID

(1) 1989MAG/DAV(b) (2) 1994DAL/HON

(3) Extrapolate

(3) This volume

TiC(O)x–O xZ0 1

TiC(CO)x–CO xZ0 1 2 3 4 5 6

TiC(H2O)x–H2O xZ0 1 2 3 N

38.0 37.7G1.4 32.6G1.2 16.0G1.6 19.9G1.8 w10.5

TiC–S

110.2G1.6

461.1G6.8

CID

2000KRE/SCH

TiC–CS

36.9G1.4

154.4G5.8

CID

2000KRE/SCH

TiC(O)–S

27.4G4.6

114.8G19.3

CID

2000KRE/SCH

(continued)

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Table 14.1.2 (continued) BDEs of TiC– and TiK–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

TiC–N –NH –NH2

119.7G3.0 111.4G2.8 85.1G3

501G13 466G12 356G13

GIB MS

1990CLE/SUN

TiC(NH3)x–NH3 xZ0 1 2 3

47.1G1.7 42.1G3.6 44.0G4.3 38.5G2.2

197G7 176G15 184G18 161G9

GIB MS

1998WAL/ARM

TiC–pyridine –pyrimidine

52.2G2.2 51.3G2.5

218.4G9.3 214.8G10.5

CID

2000ROD/STA 2001AMU/ROD

TiC–adenine

%82.1G3.5

%343.4G14.8

GIB MS

2002ROD/ARM

TiC–imidazole

R41.9G0.6 %55.5G2.0

R175.5G2.6 %232.4G8.2

CID

2004RAN/AMU

TiC–Si –SiH –SiH2 –SiH3

59.5G3.9 53.0G2.5 50.0G1.6 39.0G4.2

249G16 222G10 209G7 163G17

CID

1994KIC/ARM

TiC–Si(CH3)2 –SiH(CH3)

O60 O60

O251 O251

GIB MS

1986HAY/KRU

(OTi)K–O

150

628

Derived

2000SCH/SCH

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BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X Bonds

679

14.2 Zr– and Zr+–X bonds 14.2.1 Zr–X bonds Table 14.2.1 BDEs of Zr–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Zr–Zr

(1) 71.3G0.1 (2) 35.5

298.2G0.1 148.4

(1) Spectrometry (2) Review

(1) 1994ARR/BLU (2) 1996SMI/YAT

Zr–Ti

51.2G0.1

214.3G0.1

Spectrometry

1995LAN/MOR

Zr–V

62.3G0.1

260.7G0.3

Spectrometry

1995LAN/MOR

Zr–Co –Ni

73.23G0.02 66.9G0.1

306.39G0.10 279. 8G0.1

Spectrometry

1994ARR/BLU

(1) 83.9G1.8 (1) 74.4G1.5 (2) 78G1

351.0G7.5 311.3G6.3 326.4G4

(1) Calorimetry

(1) 1988SCH/MAR

(2) Re-cal.

(2) 1995KIN/MAR

83.2G3.1 78.7G1.7

348.1G13.0 329.3G7.1

Calorimetry

1988SCH/MAR

(1) Derived (2) Derived (3) Derived from DfH0 in ref. (4) Derived

(1) 1966MUR/HIL (2) 1991BAR/TSI (3) 1996NIST

Zr(H)x(h5-C5Me5)2–H xZ0 1

Zr(h5-C5Me5)2(O-tBu)–H Zr(h5-C5Me5)2(Ph)–H

Zr(F)x–F xZ0

1

2

(1) 148 619 (2) 147.2G3.6 616G15 (3) 145 607 (4) (1) (2) (3) (4) (1) (2)

149.9G2.5 176 148.9G3.8 172.2 161.2G2.5 141G5 160.6G4.3

627.2G10.5 736 623G16 720 674.5G10.5 590G21 672G18

(4) 1997HIL/LAU

(continued)

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Table 14.2.1 (continued) BDEs of Zr–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

3

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (3) (4) (1) (2) (3) (4)

149.8 149.6G4.5 156G5 158.9G3.6 154.8 157.9G2.5

kJ/mol

Methods (reference in parentheses)

References

627 625.9G18.9 653G21 665G15 648 660.7G10.5

Zr(Cl)x–Cl xZ0 1 2 3

126.7 122.6 109.8 115.9

530 513 459 485

Derived from DfH0 in ref.

1996NIST

Zr(h5-C5Me5)2–Cl –Br

115.0 98.0

481.2 410.0

Review

1992DRA/WON

Zr(Br)x–Br xZ0 1 2 3

100.5 140.4 88.0 77.8

420 587 368 326

Derived from DfH0 in ref.

1996NIST

(1) (2) (1) (2) (1) (2) (1) (2)

305.4 127 359.9 764 384.9 262 334.7 247

(1) Derived (2) Derived from DfH0 in ref.

(1) 1978KLE/CUB (2) 1996NIST

243

Calorimetry

1999KIN/BEL

Zr(I)x–I xZ0 1 2 3

ZrCptt2 –I, CpttZh5-1,3-di-tertbutylcyclopentadienyl

73 30.3 86 182.7 92 62.6 80 59.1

58.0

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BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X Bonds

681

Zr(I)(h5-C5Me5)2–I

80.4G0.5

336.4G2.1

Re-cal.

1995KIN/MAR

Zr–C

(1) (2) (3) (1)

561G25 306.4 495.8G38.6 581

(1) Review (2) Spectroscopy (3) Derived

(1) 1990SIM/BEA (2) 1994ARR/BLU (3) 1996SIE/CHE(b)

801

(1) Derived from DfH0 in ref. (2) Derived

(1) 1996NIST

–C2

Zr(O)x–O xZ0

1

134G6 73.2 118.5G9.2 139

(1) 191.4

(2) 183.1G2.5 766.1G10.6 (1) 142 594

(2) 2000SIM/MIT

Zr–S

(1) 137.5G4 575.3G16.7 (2) 136.7G2.8 572.0G11.6

(1) MS (2) Spectroscopy

(1) 1975STE/CAT (2) 2002RED/AHA

Zr–N

135G6

565G25

MS

1968GIN(b)

Zr(surf.)–O2

258

1080

Review

1982RAO/KAM

Zr(polycr. surf.)–CO

150

627

Calorimetry

1965BRE/HAY

ZrO2(surf.)–CO

w14.3

w60

Calorimetry

1998BOL/CER

Zr(h5-C5Me5)2(Ph)(OH)x–OH xZ0 1

115.3G1.5 115.4G2.5

482.4G6.3 482.8G10.5

Calorimetry

1988SCH/MAR

Zr(h5-C5Me5)2(NH2)H–NH2

100.7G3.6

421.3G15.1

Calorimetry

1988SCH/MAR

Zr(h5-C5H5)2(CH3)–CH3 Zr(h5-C5Me5)3–CH3

68.1G0.5 66.0G2.4

284.9G2.1 276G10

Review

1994NOL

Zr(h5-C5Me5)2(OPh)–CH3

70.6G1.0

295.4G4.2

Calorimetry

1988SCH/MAR

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 14.2.1 (continued) BDEs of Zr–X Bonds

The broken bonds (boldfaceZ dissociated fragment) Zr(h5-C5Me5)(CH3)x–CH3 xZ0 1

2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (1) (2) (3) (1)

72.8G2.4 67.7G2.1 67.9G0.5 67G1 64.6G1.9

kJ/mol

Methods (reference in parentheses)

References

304.6G10.0 283.3G8.8 284.1G2.1 280.3G4 270.3G7.9

(1) Calorimetry

(1) 1988SCH/MAR

(2) Review (3) Re-cal.

(2) 1994NOL (3) 1995KIN/MAR

Zr(h5-C5H5)2Si(SiMe3)3–CH3

66G5

276G21

Calorimetry

1995KIN/MAR

ZrO2(110, surf)–H2CO

28

117.2

Re-anal.

2001MAD/IDR

Zr–CH3OCH3

19.1G0.5

80G2

PEI-ZEKE

2001PED/ZGI

Zr(h5-C5Me5)2(CF3CH2O)– CF3CH2O

103.2G2

431.8G8.4

Re-cal.

1995KIN/MAR

Zr(tC4H9O)(h5-C5H5)2–SiMe3 Zr(h5-C5H5)2(Si(SiMe3)3)– SiMe3

59G5 45G7

247G21 188G30

Re-cal.

1995KIN/MAR

Zr(h5-C5Me5)2(OC6F5)– OtC4H9

104.6G3.0

437.6G12.6

Calorimetry

1988SCH/MAR

Zr(h5-C5H5)2(C6H5)–C6H5

71.7G2.4

300G10

Review

1994NOL

Zr(h5-C5Me5)2(C6H5)–C6H5

(1) 74.6G2.4 (2) 73.1G3.5

312.1G10 305.9G14.6

(1) Review (2) Re-cal.

(1) 1994NOL (2) 1995KIN/MAR

Zr(h5-C5Me5)2(Me)–OC6H5

90.9

380.3

Calorimetry

1988SCH/MAR

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BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X Bonds

683

Zr(h5-C5Me5)2(C6F5O)–OC6F5

105G3

439G13

Re-cal.

1995KIN/MAR

(h5-C5H5)2Zr(L)–Si(SiMe3)3 LZCl Me SiMe3

57G3 56G5 42G11

239G13 234G21 176G46

Calorimetry

1995KIN/MAR

Methods (reference in parentheses)

References

14.2.2 ZrC–X bonds Table 14.2.2 BDEs of ZrD–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

ZrC–Zr

97.3G2.3

407.0G9.6

Photofrag.

2004AYD/LOM

ZrC–Ar

8.63G0.06

36.09G0.24

PI

1995ASH/BEL

ZrC–H

(1) 53.0G1.8 (2) 52.3G2.3

221.7G7.5 218.8G9.6

GIB MS

(1) 1996SIE/CHE (2) 2003ARM/SIE

ZrC–2H

115.8G3

484G13

GIB MS

2003SIE/ARM

ZrC(H2)x–H2 xZ0 1 2 3 4 5 6

14.5G0.3 10.7G0.2 10.1G0.3 9.1G0.5 9.2G0.5 8.6G0.6 8.5G0.8

60.7G1.3 44.8G0.8 42.3G1.3 38.1G2.1 38.5G2.1 36.0G2.5 35.6G3.3

Equilibrium

2001BUS/KEM

GIB MS

(1) 1996SIE/CHE(b) (2) 2003ARM/SIE (3) 2003SIE/ARM

ZrC–C

(1) 108.8G2.5 455G11 (2) 112.5G3.5 471G15 (3) 106.5G3.7 445.8G15.4

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 14.2.2 (continued) BDEs of ZrC–X Bonds

The broken bonds (boldfaceZdissociated fragment) –CH

–CH2

–CH3

–(H)(CH3)

ZrC–C2H –C2H2 –C2H3 –C2H4 –C2H5

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (2) (3) (4) (2) (3) (4) (2) (3) (4) (3)

137.4G5.1 135.8G3 139.1G3.1 106.5G1.6 106.3G1.2 107.3G1.2 53.0G5.5 54.4G2.3 58.3G3.6 125.2G3.5

kJ/mol 575G21 568G13 582G13 445.8G7 444.8G5 449G5 222G23 227.7G9.6 244G15 524G14

(1) 105.4G2.8 441G12 (1) (2) (1) (1) (3) (1)

65.3G3.5 59G3 87.2G5.5 65.5G4.2 35 54.7G3.9

Methods (reference in parentheses)

273G14 247G13 365G23 274G17 146.4 229G16

References

(4) 1999ARM(c)

(1) Ion reactions

(1) 2003SIE/ARM

(2) PD

(2) 1995RAN/FRE

(3) Review

(3) 1998SCH/SCH

GIB MS

2003SIE/ARM

ZrC–C3H2 –C3H3 –C3H4 –C3H6

125.7G4.6 R94.5G5.3 O65.5 O28.1

ZrC(O)x–O xZ0 1

(1) 180.0G2.5 753G11 (2) 89.0G1.6 372.4G6.7

CID

(1) 1996SIE/CHE(b) (2) 1999SIE/ARM

ZrC(S)–O

101.9G4.2

426.5G17.4

Derived

2006KRE/SCH

ZrC–O2

156.3

654

Review

2006SCH

526G19 R396G22 O274 O118

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BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X Bonds

685

ZrC(O)x–CO xZ0 1

18.4G2.4 19.4G1.8

77G10 81.0G7.7

CID

1999SIE/ARM

ZrC(O2)–CO ZrC(O)–CO2

23.3G1.8 17.1G1.4

97.4G7.7 71.4G5.8

CID

1999SIE/ARM

ZrC–S

(1) 127.4G5 533G21 (2) 131.2G2.3 549.0G9.6

Ion reactions

(1) 2003ARM (2) 2006KRE/SCH

ZrC(O)–S

54.4G10.1

227.7G42.5

Derived

2006KRE/SCH

ZrC(S)–S

88.1G15.7

368.6G65.6

Derived

2006KRE/SCH

ZrC–CS

(1) 61.7G2.6 (2) 61.6G2.5

258G11 257.6G10.6

Ion reactions

(1) 2000ROD/ARM(b) (2) 2006KRE/SCH

ZrC–N

(1) 110G13 (2) 106G11

460G54 443G46

(1) Derived (2) Der. from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

14.3 Hf– and HfC –X bonds Table 14.3 BDEs of Hf– and HfD–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Hf–Hf

78.4G14

328G58

Hf(H)(h5-C5Me5)2–H

(1) 76.8G0.8 321.3G3.3 (2) 82.7G1.9 346.0G7.9

Methods (reference in parentheses)

References

Correlation

1986MOR

(1) Calorimetry (2) Review

(1) 1988SCH/MAR (2) 1994NOL (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 14.3 (continued) BDEs of Hf– and HfC–X Bonds

The broken bonds (boldfaceZdissociated fragment) Hf(F)x–F xZ0 1 2 3

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

References

650G15 642G14 640G20 702G18

MS

1991BAR/TSI

HfCptt2 –I Cptt: h5-1,3-di-tert- 61.2 butylcyclopentadienyl

256

Calorimetry

1999KIN/BEL

Hf–O

191.4G3.1

801G13

Review

1990SIM/BEA

Hf–N

127.9G7.2

535G30

MS

1974KOH/STE

Hf–C –C2

129G6 161

540G25 674

Review

1990SIM/BEA

HfO2(surf.)–O2

271

1134

Review

1982RAO/KAM

HfO2(surf.)–CO

w14.3

w60

Calorimetry

1998BOL/CER

(1) (1) (2) (1) (2)

305.0G5.9 296.6G3.8 305.9G7.5 290.4G3.3 294G10

(1) Calorimetry

(1) 1988SCH/MAR

(2) Review

(2) 1994NOL

Hf(h5-C5Me5)(CH3)x–CH3 xZ0 1 2

155G3.6 153.4G3.3 153.0G4.8 167.8G4.3

kJ/mol

Methods (reference in parentheses)

72.9G1.4 70.9G0.9 73.1G1.8 69.4G0.8 70.3G2.4

Hf(h5-C5Me5)(C4H9)–C4H9

65.5G2.4

274G10

Review

1994NOL

HfC–H

55.8

233.5

Review

1990OHA/GOD

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BDEs of Ti(TiG)–, Zr(ZrC)–, and Hf(HfC)–X Bonds HfC–CH2

687

102G9

427G38

ICR

1991IRI/BEA

(1) 173G5 (2) 173.8 (2) 110.7

724G21 727 463

(1) Derived (2) Review

(1) 2000SCH/SCH (2) 2006SCH

HfC–O2

166.6

697

Review

2006SCH

HfC–N

55G10

229G42

Derived from IP in ref.

1996NIST

HfC–C2H4

36

150.6

Review

1998SCH/SCH

HfC(O)x–O xZ0 1

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chapter fifteen

BDEs of V(V G)–, Nb(Nb C )–, and Ta(TaC)–X bonds 15.1 V–, VC–, and VK–X bonds 15.1.1 V–X bonds Table 15.1.1 BDEs of V–X Bonds

The broken bonds (boldfaceZdissociated atom) V–V

V(V)x–V xZ1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17

BDEs (boldfaceZ recommended data; reference in parentheses) kJ/mol

Methods (reference in parentheses)

(1) 56.9G5 (2) 57.8 (3) 43.6 (4) 64.4G0.1 (5) 61.3

238G21 242 182.4 269.3G0.1 256.5

(1) MS (2) Review (3) Spectrometry (4) Spectrometry (5) Review

(1) 1969KAN/LIN (2) 1979MIE/GIN (3) 1984LAN/MOR (4) 1992SPA/MOR(b) (5) 1996SMI/YAT

(1) 32.7 (1) 84.6 (1) 71.0 (1) 92.9 (1) 86.0 (1) 94.8 (1) 80.9 (1) 90.6 (1) 87.2 (1) 94.3 (1) 106.8 (1) 93.4 (1) !101.9 (1) O96.6 (1) 96.9 (1) 89.0 (1) !92.7

137 354 297 389 360 397 339 379 365 395 447 391 !426 O404 405 372 !388

(1) CID

(1) 1996ARM/KIC

kcal/mol

References

(continued)

689

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Comprehensive Handbook of Chemical Bond Energies

Table 15.1.1 (continued) BDEs of V–X Bonds

The broken bonds (boldfaceZdissociated atom) N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 122.4 (3) w109.7

512 w459

(2) Review (3) Extrapolate

(2) 1994ARM/HAL (3) This volume

V–Nb

88.3G0.1

369.3G0.1

Spectrometry

1994JAM/KOW

V–Ti

48.6G0.1

203.2G0.1

Spectrometry

1992SPA/MOR(b)

V–Zr

62.3G0.1

260.6G0.3

Spectrometry

1995LAN/MOR

V–Ru –Rh

98.9G6.9 86.9G6.9

414G29 364G29

Review

1986MOR

V–Ni

49.3G0.1

206.4G0.2

Spectrometry

1990SPA/MOR

V(100, surf.)–Ag

69.4

290.4

STM

2003KRA/PER

V–Au

58.8G2.1

246.0G8.7

Review

1986MOR

V–Al

35.2G0.2

147.4G1.0

Spectrometry

2001FU/RUS

V–H

(1) 37.9G3 (2) 41.1G4 (3) 50.0G1.6

159G13 172G17 209.3G6.8

(1) Ion reactions (2) Review (3) GIB MS

(1) 1985SAL/LAN (2) 1990SIM/BEA (3) 1993CHE/CLE

V–F –Cl –Br

141G15 114G15 105G10

590G63 477G63 439G42

Review

1974GUR/KAR

V(O)x–O xZ0

(1) 149.5G2 (2) 149.4G4.5 (3) 152.3

625.5G8.5 625G19 637

(1) 1983BAL/GIG (2) 1990SIM/BEA (3) 1996NIST

1

(1) 131.9G4.8 (3) 145.7

552G20 610

(1) MS (2) Review (3) Derived from DfH0 in ref.

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

691

V–S

(1) 107.4G3.5 (2) 117.1G4 (3) 114.2G0.5

449.4G14.6 490G17 477.9G1.9

MS

(1) 1967DRO/PAT (2) 1974OWZ/FRA (3) 1984BOT/EDW

V–Se

83G5

347G21

Review

1974GUR/KAR

V–N

125G9

523G38

FT-MS

1988BUC/GOR

V–C –C2

(1) 101.1G5.7 (1) 136.6G4.6 (2) 138

423G24 572G19 578

(1) MS

(1) 1981GUP/GIN

(2) Review

(2) 1990SIM/BEA

(h5-C5H5)(CO)3V–h2H2 –N2

21.5G4.8 28.7G4.8

90G20 120G20

PAC

1991JOH/POP

V(surf.)–O2

200

836

Review

1982RAO/KAM

(h5-C5H5)(CO)3V–CO

35G5

146G21

PAC

1993GEO/HAW

V–CH3

40G4

169G18

Review

1996ARM/KIC

(1) 62G5 (2) 18.2 (1) 57G5 (2) 73.6

259G21 76.2 238G21 307.8

(1) Photolysis (2) Derived

(1) 1986HET/JAC (2) 2004KAN/RAO

V(C6H6)x–C6H6 xZ0 1

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

692

Comprehensive Handbook of Chemical Bond Energies

15.1.2 VC–X bonds Table 15.1.2 BDEs of VD–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

VC(V)x–V xZ0 1 2

(1) 72.4

303

(1) CID

(1) 1994RUS/HEI

(2) 72.2

302

(2) Review

(2) 2001ARM

(2) 52.3

219 (3) PD

(3) 2001FU/RUS

(4) Radiation

(4) 2005HAN/HER

(3) 54.46G0.02

227.85G0.10

(2) 81.4

341

3

(2) 74.7

313

4

(2) 95.1

398

5

(2) 88.9

372

6

(2) 92.0

385

7

(2) 84.6

354

8

(2) 91.3

382

9

(2) 91.3

382

10

(2) 95.1

398

11

(2) 107.2

449

12

(4) 100.3

419.7

(2) 92.7

388

13

(2) 108.0

452

14

(2) 89.9

376

15

(2) 96.6

404

16

(2) 91.1

381

17

(2) 97.5

408

18

(2) 105.9

443

N

VC–Nb

(5) 122.4

512

(5) Review

(5) 1994ARM/HAL

(6) w109.7

w459

(6) Extrapolate

(6) This volume

96.4G0.1

403.5G0.2

Derived from IP

1996NIST

in ref.

VC–Fe

VC–Ar

(1) 75G5

314G21

(1) PD

(2) O63

O259

(2) Ion reactions

1987HET/FRE

(1) 6G5

25G21

(1) CID

(1) 1986ARI/ARM

(2) 9.39G0.004

39.29G0.18

(2) PD

(2) 1989LES/BRU(b)

(3) 9.41G0.03

39.39G0.12

(3) PD

(3) 1998HAY/BEL

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

VC–Kr

VC–Xe

VC–H

(CO)6VC–H

693

(1) 10G5

42G21

(1) CID

(1) 1986ARI/ARM

(2) 11.82G0.04

49.46G0.18

(2) PD

(2) 1989LES/BRU(b)

(1) 19.8G4

83G17

(1) CID

(1) 1986ARI/ARM

(2) 19.1G1.6

80G7

(2) CID

(2) 1995SIE/ARM

(3) 15.9G0.1

66.4G0.6

(3) PD

(3) 1996BEL/BUT

(1) 50G2

209G8

(1) Ion reactions

(1) 1984ARI/ARM

(2) 48.2G1.4

201.7G6

(2) Ion reactions

(2) 1985ELK/ARM

(3) 48.2G1.4

202G6

(3) Review

(3) 1990SIM/BEA

(1) 56G3

234.3G12.6

(1) Thermochemical

(1) 1981STE/BEA

(2) 52.6G3.3

220G14

(2) Review

(2) 1990SIM/BEA

Ion reactions

VC(V)x–D xZ0

(1) 48.2G1.4

202G6

1

(2) 52.1G4.2

218G17

2

(2) 42.9G4.4

179G18

3

(2) 48.9G5.8

205G24

4

(2) 54.0G7.1

226G30

5

(2) 58.6G7.4

245G31

6

(2) 60.6G4.8

254G20

7

(2) 53.5G8.8

224G37

8

(2) 63.0G5.3

264G22

9

(2) 53.3G9.2

223G39

10

(2) 59.0G7.6

247G32

11

(2) 66.2G11

277G46

12

(2) 63.9G11

267G46

58.3G2.3

243.9G9.6

CID

1998KRE/SCH

Equilibrium

1993BUS/KEM

VC(S)–D

(1) 1985ELK/ARM (2) 2002LIY/CON

VC(H2)x–H2 xZ0

10.2G0.5

42.7G2.1

1

10.7G0.5

44.8G2.1

2

8.8G0.4

36.8G1.7

3

9.0G0.4

37.7G1.7

4

4.2G0.5

17.6G2.1

5

9.6G0.5

40.2G2.1

6

!2.5

!10.5

(continued)

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

694

Comprehensive Handbook of Chemical Bond Energies

Table 15.1.2 (continued) BDEs of VC–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds atom)

Methods

reference in parentheses)

(boldfaceZdissociated

kcal/mol

(reference in

kJ/mol

parentheses)

References

VC(H2O)(H2)x–H2 xZ0

9.9G0.5

41.4G2.1

1

8.5G0.4

35.6G1.7

Equilibrium

1993BUS/KEM

2

6.9G0.7

28.9G2.9

VC(H2O)2–H2

6.7G1.5

28.0G6.3

Equilibrium

1993BUS/KEM

VC–C

(1) 88G5

368G21

GIB MS

(1) 1984ARI/ARM

(2) 89.2G3.2

373G13.5

–CH

(1) 106G5

444G21

(3) 112.4G1.2

470G5

–CH2

(1) 75G8

314G33

(3) 77.8G1.4

326G6

(2) 1991CLE/ELK (3) 1987ARI/ARM

VC(CH3)x–CH3 xZ0

(1) 50.5G3

211G13

(2) 46.1G1.7

193G7

(1) 47.5G2.4

199G10

VC(H)–CH3

46G4

192G17

GIB MS

1995SIE/ARM(b)

VC–CH4

15.0G0.9

62.8G3.6

PD

1997HAY/BEL

VC–C2

(1) GIB MS

(1) 1986ARI/ARM

(2) Re-examined

(2) 1997GID/KOP

(3) GIB MS

(3) 1986ARI

(4) Review

(4) 1996ARM/KIC

1

(1) 125.3G3.6

524G15

–C2H

(1) 117.4G1.8

491G8

–C2H2

(1) 48.9G4.6

205G19

(2) 41G2

172G8

–C2H3

(1) 88.1G4.6

369G19

–CHCH3

(3) 67G5

280G21

–C2H5

(3) 54G4

226G17

–(CH3)2

(4) 93.5G1.7

391G7

GB MS

(1) 1984ARI/ARM (2) 1986ARI/ARM

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

695

VC(C2H4)x–C2H4 xZ0

(1) 29.7G1.8

124G8

(1) CID

(1) 1998SIE/JAR

(2) 28

117.2

(2) Review

(2) 1998SCH/SCH

(1) 30.4G3.3

127G14

VC–C3H5

102G16

427G67

FT-MS

1988BUC/GOR

VC–C3H6

30.7G2

128.4G8.4

KERD

1998KOP/BOW

Multiphoto ionizat.

1992OPI/HAR

(1) 1986HET/JAC

1

VC(h5-C5H5)x–(h5-C5H5) xZ0 1

126.8

530.7

54.0

225.9

(1) 62G5

259G21

(1) PD

(2) 55.8G2.3

234G10

(2) CID

(2) 1995MEY/KHA

(3) O55

O230

(3) FT-ICR

(3) 2002GAP/DUN

(2) 58.8G4.3

246G18

(3) 60

251

FT-ICR

2002GAP/DUN

FT-ICR

2002GAP/DUN

FT-ICR

2002GAP/DUN

VC(C6H6)x–C6H6 xZ0

1

VC(Cl)(C6H6)x–C6H6 xZ0 1

65

272

!30

!126

VC(Br)(C6H6)x–C6H6 xZ0 1

65

272

!30

!126

VC(I)(C6H6)x–C6H6 xZ0 1

64

268

!30

!126

VC(O)x–O xZ0

(1) 119–151

498–632

(1) ICR

(1) 1981KAP/STA

(2) 139.0G2.3

581.6G9.6

(2) CID

(2) 1998XU/ROD

(3) 141.5G6.5

592.0G27

(3) CID

(3) 2001BEL/ZEM

(4) 137.2

574

(4) Review

(4) 2006SCH

(continued)

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

696

Comprehensive Handbook of Chemical Bond Energies

Table 15.1.2 (continued) BDEs of VC–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom) 1

kcal/mol (3) 80.9G8.3

kJ/mol

Methods (reference in parentheses)

References

339G35

(4) 78.9

330

(5) 70.6G9.2

295G39

(5) CID

(5) 1995SIE/ARM(b)

Review

2001ARM

Review

2001ARM

Ion reactions

1998KRE/SCH

VC(V)x–O xZ1

117.6

492

2

168.3

704

3

173.0

724

4

168.3

704

5

170.7

714

6

161.3

675

7

129.1

540

8

138.4

579

9

154.4

646

10

122.1

511

11

103.7

434

12

117.6

492

13

124.5

521

14

136.0

569

VC x –2O xZ1

210.8

882

2

299.7

1254

3

318.1

1331

4

338.4

1416

5

351.8

1472

6

345.8

1447

7

328.4

1374

8

308.1

1289

9

316.4

1324

10

291.6

1220

11

289.2

1210

12

285.9

1196

13

292.3

1223

14

270.3

1131

15

276.8

1158

82.3G3.9

344G16

VC(S)–O

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

VC–O2

VC–OH

98.2

697

411

Review

GIB MS

2006SCH

(1) 107.0

448

(2) 103.8G3.5

434G15

(1) 1989MAG/DAV(b)

VC–OD

101.7G4.4

426G18

GIB MS

1994CLE/CHE

VC(O)–CO

(1) 37

154

(1) PD

(1) 1991LES/ASH(c)

(2) 24.2G2.3

101G10

(2) CID

(2) 1995SIE/ARM(b)

CID

1995SIE/ARM

1995SIE/ARM(b)

(2) 1993CLE/ARI

VC(CO)x–CO xZ0

27.4G0.7

114.8G2.9

1

21.0G0.7

87.8G2.9

2

17.3G0.9

72.3G3.9

3

21.9G2.3

91.7G9.6

4

22.1G0.7

92.6G2.9

5

24.9G1.6

104.2G6.7

6

12.7G2.1

53.1G8.7

VC–CO2

17.3G0.9

72.4G3.8

CID

(1) 36.2

151.5

CID

(2) 35.1

146.9

(2) 1989MAR/SQU (3) 1994DAL/HON

VC(H2O)x–H2O xZ0

(3) 35.8G1.2

149.8G5.0

1

(2) 35.5

148.5

(3) 36.0G2.3

150.6G9.6

2

(2) 12.1

50.6

(3) 16.2G1.1

67.8G4.6

3

(3) 16.0G1.8

66.9G7.5

87.6G4.6

366.6G19.3

PES

(1) 87.2G2.3

364.8G10

Ion reactions

(2) 85.7G2.1

358.9G8.7

OVC(OCD3)2–OCD3

(1) 1989MAG/DAV(b)

2004SCH/LOO

VC(S)x–S xZ0

(1) 1998KRE/SCH (2) 1999RUE/ARM

(continued)

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

698

Comprehensive Handbook of Chemical Bond Energies

Table 15.1.2 (continued) BDEs of VC–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom) 1 2

kcal/mol

Methods (reference in

kJ/mol

(1) R72.4G0.1

R303.0G0.4

(3) 89.7G2.5

375.3G10.6

(3) 78.6G3.7

329.0G15.4

parentheses)

References

(3) 2003KRE/SCH

VC(S)x–S2 xZ0

74.9G3.2

313.6G13.5

1

68.5G4.4

286.6G18.3

VC(O)–S

31.4G5

VC–SD –CS –CS2

VC–N –NH –NH2

Ion reactions

2003KRE/SCH

131G21

Ion reactions

1998KRE/SCH

59.3G3.5

248G15

Ion reactions

1998KRE/SCH

39.2G1.8

164G8

27.2G3.0

113.8G12.5

(1) 107.2G1.4

448.6G5.8

(1) GIB MS

(1) 1990CLE/SUN(b)

(1) 99.2G3.7

415G15 (2) GIB MS

(2) 1988BUC/GOR

(2) 101G7

423G29

(1) 73.3G2.3

306.8G9.6

(3) 70.0G1.4

293G6

(3) Review

(3) 1996ARM/KIC

CID

(1) 1989MAR/SQU

VC(NH3)x–NH3 xZ0 1 2 3

VC–pyridine –pyrimidine

(1) 51.9

217.1

(2) 45.9G2.6

192G11

(1) 45

188

(2) 39.2G2.2

164G9

(1) 22.6

94.6

(2) 26.1G2.6

109G11

(1) 18.7

78.2

(2) 23.7G2.4

99G10

52.6G3.2

220.1G13.5

49.1G1.7

205.4G7.3

(2) 1998WAL/ARM

CID

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

2000ROD/STA 2001AMU/ROD

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

699

VC–pyrrole

O41

O172

Kinetics

2000GAP/YAN

VC–adenine

%64.4G2.6

%269.3G11

CID

2002ROD/ARM

CID

2004RAN/AMU

Ion reactions

1994KIC/ARM

Ion reactions

1986HAY/KRU

Ion reactions

2002SCH/ENG

VC–imidazole

VC–Si

R52.9G0.6

R221.1G4.6

%58.2G1.9

%243.4G8.0

54.7G3.5

229G15

–SiH

48.2G2.8

202G12

–SiH2

46.6G2.1

195G9

–SiH3

35.5G3.7

149G16

VC–SiHCH3

O60

O251

–Si(CH3)2

O60

O251

V2C–O –OH

92.2G6.9

385.9G28.9

73.8G9.2

308.7G38.6

15.1.3 VK–X bonds Table 15.1.3 BDEs of VL–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom) (O2)VK–O

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

125.2G7.1

524G30

CID

2001BEL/ZEM

xZ2

(1) 35.8G4.4

150G18

CID

(1) 1993SUN/WAN

3

(1) 40.4G5.8

169G24

(2) 34G6

142G25

4

(1) 31.1G3.0

130G13

(2) 29G6

121G25

VK(CO)x–CO

(2) 1992SUN/SQU

(continued)

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

700

Comprehensive Handbook of Chemical Bond Energies

Table 15.1.3 (continued) BDEs of VK–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

Methods

reference in parentheses)

(boldfaceZdissociated atom)

kcal/mol

5

kJ/mol

(1) 30.8G3.5

129G15

(2) 35G6

146G25

(reference in parentheses)

References

(h5-C5H5)VK(CO)x–CO xZ1

42.1G3.3

176G14

2

43.5G3.8

182G16

CID

1999SUN/SQU

PES

1997JUD/HIR

VK(C6H5F)x–C6H5F xZ0 1

14.4G3.8

60.2G16

3G15

12.6G63

15.2 Nb– and NbC–X bonds 15.2.1 Nb–X bonds Table 15.2.1 BDEs of Nb–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom) Nb–Nb

Nb(Nb)x–Nb xZ1 2

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 127.3

532.4

(1) Review

(1) 1996SMI/YAT

(2) 122.6

513

(2) CID

(2) 1996ARM/KIC

(3) 126.1G2.3

527.6G9.6

(3) Photofrag.

(3) 2004AYD/LOM

(1) 107.1

448

(1) CID

(1) 1996ARM/KIC

(1) 136.5

571

3

(1) 128.8

539

4

(1) 134.1

561

5

(1) 154.6

647

6

(1) 145.8

610

7

(1) 130.5

546

8 9

(1) 150.8 (1) 126.2

631 528

N

(2) 174.3

729

(2) Review

(2) 1994ARM/HAL

(3) w163

w682

(3) Extrapolate

(3) This volume

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

701

Nb–V

88.3G0.1

369.3G0.1

Spectrometry

1994JAM/KOW

Nb(polysc.)–Na

62.3

260.5

TD

1971STE/FAD

Nb(polysc.)–K

57.7

241.2

TD

1971STE/FAD

Nb(110, surf.)–Cs

55.8

233.5

TDS

1993MAG/DAV

Nb(110, surf.)–Ba

85.8

358.9

TDS

1993MAG/DAV

Nb–Ti

72.2G0.1

302.0G0.1

Spectrometry

1995LAN/MOR

Nb–Cr

70.68G0.01

295.72G0.06

Spectrometry

2000SIC/LAN

Nb–Mo

108G6

452G25

Review

1986MOR

Nb–Co

63.82G0.02

267.02G0.10

Spectrometry

1994ARR/BLU

Nb–Ir

111G6

464G25

Review

1986MOR

Nb–Ni

65.0G0.1

271.9G0.1

Spectrometry

1994ARR/BLU

Nb–H

O53.0G2.3

O221.9G9.6

Ion reactions

2000SIE/CHE

Nb(100, surf.)–H

65.0

272

Review

1988CHR

Nb(polycs. surf.)–F

117.6G3.5

492G14

Ion beam

1979BOL/BLA

Nb(100, surf.)–F

109

456

Ion beam

1981BOL/BLA

(continued)

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

702

Comprehensive Handbook of Chemical Bond Energies

Table 15.2.1 (continued) BDEs of Nb–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Nb(111, surf.)–F

108

452

Ion beam

1981BOL/BLA

Nb(polycs. surf.)–Cl

101.5G3.5

425G14

Ion beam

1979BOL/BLA

Nb(100, surf.)–Cl

92

385

Ion beam

1981BOL/BLA

Nb(111, surf.)–Cl

94

393

Ion beam

1981BOL/BLA

Nb(polycs. surf.)–Br

92.2G3.5

386G14

Ion beam

1979BOL/BLA

Nb(100, surf.)–Br

83

347

Ion beam

1981BOL/BLA

Nb(111, surf.)–Br

83

347

Ion beam

1981BOL/BLA

Nb(polycs. surf.)–I

72.6G3.5

304G14

Ion beam

1979BOL/BLA

(1) 180.8 (2) 183.8G6

756 769G25

(1) Spectroscopy (2) Review

(1) 1979HUB/HER (2) 1990SIM/BEA

(3) 187.3

784

(3) Derived from

(3) 1996NIST

Nb(O)x–O xZ0

DfH0 in ref. (4) 173.6G2.5

726.5G10.6

(3) 154.9

648

Nb2–O

O85.3G11.5

Nb–C

1

(4) Derived

(4) 2000SIM/MIT

O357G48

GIB MS

1989LOH/LIA

(1) 134.8G3.1 (2) 135.8G3.1

564G13 568G13

(1) MS (2) Review

(1) 1981GUP/GIN (2) 1990SIM/BEA

(3) 125.2G3.5

523.8G14.5

(3) LIF/R2PI

(3) 1997SIM/PRE

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

–C2

703

(1) 155.4G3.8

650G16

(2) 157

656

Nb(polycr. surf.)–H2

w78

w326

TD

1974KO/SCH

Nb(100, surf.)–H2

26.5 (phys)

111

Review

1978MAD/BEN

Nb(110, surf.)–H2

14.8G0.2 (phys)

61.9G0.8

Kinetics

1981PIC

Nb(polycr. surf.)–O2

(1) 207.7

869

(1) Calorimetry

(1) 1960BRE/HAY

(2) 194

812

(2) Review

(2) 1982RAO/KAM

O120

O502

TD

1974KO/SCH

xZ0

65–78

270–328

PI

2004PED/RAY

1

39–42

164–174

Nb(polycr. surf.)–CO

132

522

Calorimetry

1965BRE/HAY

Nb(110, surf.)–CO

6.9 (phys)

28.9

TDS

1967DEG(c)

15

63

33.7

141

39.9

167

57.0

238

69

289

Nb(polycr. surf.)–N2

Nb3(CO)x–CO

Nb(polycr. surf.)–CO2

(1) 132

552

(1) Review

(1) 1964HAY/TRA

(2) 152

636

(2) Calorimetry

(2) 1965BRE/HAY

IR-NMR

2004BAK/BAK

Nb(h5-C5H5)2H3–TFE

4.5G0.3

18.8G1.3

–HFIP

5.7G0.3

23.8G1.3

TFEZtrifluoroethanol HFIPZhexafluoroisopropanol

7366—CHAPTER 15—3/2/2007—08:23—SHANMUGAM—15371—XML MODEL B – pp. 689–712

704

Comprehensive Handbook of Chemical Bond Energies

15.2.2 NbC–X bonds Table 15.2.2 BDEs of NbD–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds atom)

Methods

reference in parentheses)

(boldfaceZdissociated

kcal/mol

(reference in

kJ/mol

parentheses)

References

NbC(Nb)x–Nb

(1) 136.0

569

(1) CID

(1) 1996ARM/KIC

xZ0

(2) 137.9G2.3

576.8G9.6

(2) Photofrag.

(2) 2004AYD/LOM

1

(1) 117.1

490

.

2

(1) 141.0

590

(2) 138.2G0.1

578.3G0.4

3

(1) 133.1

557

4

(1) 135.8

568

5

(1) 155.4

650

6

(1) 141.5

592

7

(1) 138.1

578

8

(1) 144.4

604

9

(1) 143.4

600

N

(3) 174.3

729

(3) Review

(3) 1994ARM/HAL

(4) w163

w682

(4) Extrapolate

(4) This volume

96.7G0.1

404.7G0.2

Derived from IP in

1996NIST

NbC–V

ref.

NbC–Fe

(1) 68G5

285G21

(1) PD

(1) 1987HET/FRE

(2) O60

O251

(2) Ion reactions

(2) 1989BUC/FRE

NbC–Ar

9.77G0.03

40.87G0.13

PD

1996BUT/BEL

NbC–Xe

17.51G0.03

73.28G0.12

PD

1997BEL/BUT

NbC–H

(1) 53G3

222G13

(1) PD

(1) 1987HET/FRE

(2) 52.6G1.6

220G7

(2) GIB MS

(2) 1996SIE/CHE

PD

1987HET/JAC

NbC(C)–H

!88

!368

NbC(CH)–H

64G5

268G21

7366—CHAPTER 15—3/2/2007—08:24—SHANMUGAM—15371—XML MODEL B – pp. 689–712

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

705

NbC(H2)x–H2 xZ0

14.8

61.9

1

15.6

65.3

2

14.3

59.8

3

15.4

64.4

4

16.6

69.5

5

14.3

59.8

6

13.4

56.1

7

!1.0

!4.2

NbC–C

–CH

Equilibrium

1999BOW/KEM

(1) 135G31

565G130

(1) Ion reactions

(1) 1987HET/JAC

(2) 119.0G3.5

498G15

(2) GIB MS

(2) 1996SIE/CHE(b)

(3) 121.8G3.5

509G15

(3) GIB MS

(3) 2000SIE/CHE

(1) 145G8

607G33 (4) GIB MS

(4) 1999ARM(c)

(3) 138.8G4.6

581G19

(4) 142.7G5.5

597G23

(1) 109G7

456G29

(3) 102.4G2.1

428.4G8.7

(4) 106.1G0.7

444G3

(3) 47.5G2.5

198.8G10.6

Nb2C–CH2

197G10

824G42

Ion reactions

1987BUC/FRE

NbC–CHC 2

107G10

448G42

Ion reactions

1987BUC/FRE

NbC n –C2 ; ðnZ 2–6Þ

R186.3

R779

FT ICR

1995JIA/FRE

NbC(H)–CH3

110.2G2.5

461.2G10.6

Ion reactions

2000SIE/CHE

NbC–CH3NH2

32.1

134

HP MS

1990GUO/CAS

(1) Ion reactions

(1) 2000SIE/CHE

(2) PD

(2) 1995RAN/FRE

(3) Review

(3) 1998SCH/SCH

–CH2

–CH3

NbC–C2H –C2H2 –C2H3 –C2H4 –C2H5

(1) 100.1G1.4

418.7G5.8

(1) 66.9G1.4

279.8G5.8

(2) 57G3

238G13

(1) 79.1G4.8

331G20

(1) 64.6G6.9

270G29

(3) 37

154.8

(1) 56.5G2.8

236.4G11.6

(continued)

7366—CHAPTER 15—3/2/2007—08:24—SHANMUGAM—15371—XML MODEL B – pp. 689–712

706

Comprehensive Handbook of Chemical Bond Energies

Table 15.2.2 (continued) BDEs of NbC–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom) NbC–C3H2

kcal/mol

kJ/mol

121.1G4.4

506.5G18.3

–C3H3

R86.7G5.3

R363G22

–C3H4

O65.5

O274.0

–C3H5

R32.3G2.3

R135.1G9.6

–C3H6

O28.1

117.7

O39

(NbFe)C–C3H4

Methods (reference in parentheses)

References

Ion reactions

2000SIE/CHE

O163

Ion reactions

1989BUC/FRE

Ion reactions

1989BUC/FRE

(NbFe)C(B)x–B BZcyclopentadiene xZ0

O32

O134

1

O32

O134

(NbFe)C

O36

O151

Ion reactions

1989BUC/FRE

Ion reactions

1989BUC/FRE

–cyclohexadiene

(NbFe)C(B)x–B BZcycloheptatriene xZ0 1

NbC–C6H4

O68G5

O285G21

O47

O197

R79

R331

Ion reactions

1991BUC/GOR

Ion reactions

1989BUC/FRE

Ion reactions

1989BUC/FRE

NbC(Fe)x–C6H6 xZ0 1

NbC–C7H8

66G7

276G29

O30

O126

61G12

255G50

7366—CHAPTER 15—3/2/2007—08:24—SHANMUGAM—15371—XML MODEL B – pp. 689–712

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

707

NbC(O)x–O xZ0

(1) w194

w812

(1) CID

(1) 1989BUC/FRE

(2) 164.4G2.5

688G11

(2) CID

(2) 1996SIE/CHE(b)

(3) 167.3

700

(3) Review

(3) 2006SCH

(4) 131.7G3.9

551.0G16.4

(4) CID

(4) 1998SIE/ARM

NbC(S)–O

129.4G3.7

541.3G15.4

Derived

2006KRE/SCH

NbC–O2

180.9

757

Review

2006SCH

NbFeC–O

O85

O356

Ion reactions

1989BUC/FRE

O119

O498

Ion reactions

1989BUC/FRE

xZ0

22.8G1.2

95.5G4.8

CID

1998SIE/ARM

1

25.4G1.2

106.1G4.8

2

25.6G1.2

107.1G4.8

NbC(O)–CO2

20.3G0.7

84.9G2.9

CID

1998SIE/ARM

Nb4 CC 4 –OH

119

498

FT ICR

1995YEH/BYU

104

435

Ion reactions

(1) 2003ARM

1

NbFeOC x –O; x Z1,2

NbC(O)x–CO

–OCH3

NbC–S

(1) 127.2G2.4

532G10

(2) 119.9G4.8

501.7G20.3

NbC(O)–S

84.9G7.1

355G30

Derived

2006KRE/SCH

NbC(S)–S

O103.8G0.9

O434.2G3.9

Derived

2006KRE/SCH

(2) 2006KRE/SCH

(continued)

7366—CHAPTER 15—3/2/2007—08:24—SHANMUGAM—15371—XML MODEL B – pp. 689–712

708

Comprehensive Handbook of Chemical Bond Energies

Table 15.2.2 (continued) BDEs of NbC–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds atom) NbC–CS

Methods

reference in parentheses)

(boldfaceZdissociated

kcal/mol

(reference in

kJ/mol

(1) 57.8G2.6

242G11

(2) 57.9G2.5

242.2G10.6

parentheses) Ion reactions

References (1) 2000ROD/ARM(b) (2) 2006KRE/SCH

NbC x –N2 nZ7

!51.4

!215

8

!51.4

!215

197G10

824G42

R74

R310

107G10

448G42

R7

R29

w125G7

w523G29

O119

O498

Nb2C–CH2 –C2H2

Nb2C–CHC 2

–C2 HC 2

Nb2C–O Nb3C–O

O119.2G0.2

O498.7G0.8

Nb2C–O2

O106.1G3.5

O444G15

Ion reactions

1986BRU/PET

FT-MS

1988GOR/FRE

FT-MS

1988GOR/FRE

CID

1989LOH/LIA

15.3 Ta– and TaC–X bonds 15.3.1 Ta–X bonds Table 15.3.1 BDEs of Ta–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

The broken bonds (boldfaceZdissociated atom)

kcal/mol

Ta–Ta

93G23

390G96

Correlation

1986MOR

Ta(110, surf.)–La –Ce

126.8G4.6 140.7G4.6

531G19.3 589G19.3

TD

1974MED

kJ/mol

7366—CHAPTER 15—3/2/2007—08:24—SHANMUGAM—15371—XML MODEL B – pp. 689–712

References

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

–Pr –Nd

709

117.6G4.6 108.4G4.6

492G19.3 453G19.3

Ta(110, surf.)–Sm –Eu –Gd –Tb

48.4G6.9 41.5G4.6 99.2G4.6 94.5G9.2

203G29 174G19.3 415G19.3 396G39

TD

1974MED

Ta(110, surf.)–Ho –Er –Tm –Lu

53.0G4.6 73.8G4.6 27.7G4.6 103.8G4.6

222G19.3 309G19.3 116G19.3 434G19.3

TD

1974MED

Ta(110, surf.)–Pd

11.3G0.5 (phys)

47.3G1.9

FIM

1988SCH/KEL

Ta(110, surf.)–Pd

115

481

Review

1995SEE/ALL

Ta(110, surf.)–Hg

12.7G1.4 (phys) 53.1G5.8

FEM

1975BOB/MIR

Ta(121, surf.)–Hg

8.8G1.8

36.7G7.7

FEM

1975BOB/MIR

Ta(211, surf.)–Hg

10.4G1.2

43.4G4.8

FEM

1975BOB/MIR

Ta(111, surf.)–Hg

42

176

Review

1995SEE/ALL

TaS2(surf.)–He

0.2

0.8

HAS

1989BRU/HEI

Ta(F)x–F xZ0 1 2 3 4

137G3 157G3 144G3 130G3 138G3

573G13 657G13 602G13 544G13 577G13

MS

1979LAU/HIL

(continued)

7366—CHAPTER 15—3/2/2007—08:24—SHANMUGAM—15371—XML MODEL B – pp. 689–712

710

Comprehensive Handbook of Chemical Bond Energies

Table 15.3.1 (continued) BDEs of Ta–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom)

kcal/mol

Ta(polycs. surf.)–F

115.3G3.5

482G14

Ion beam

1979BOL/BLA

Ta–Cl

130

544

Est. by exp.

1980BEH/FEB

Ta(polycs. surf.)–Cl

(1) 110 (2) 96.9G3.5

460 405G14

(1) MS (2) Ion beam

(1) 1975WEB/PHI (2) 1979BOL/BLA

Ta(polycs. surf.)–Br

62.2G3.5

261G14

Ion beam

1979BOL/BLA

(1) 191G3 (2) 200.5

799G13 839

(1) 1990SIM/BEA (2) 1996NIST

(3) 189.8G3.9 (2) 153.6

793.9G16.4 643

(1) Review (2) Der. from DfH0 in ref. (3) Spectroscopy

(3) 2002RED/AHA

Ta–S

160.0G3.2

669.5G13.5

Spectroscopy

2002RED/AHA

Ta–N

145G20

607G84

Review

1974GUR/KAR

Ta(polycr. surf.)–H2

38.0 (phys)

159

Calorimetry

1950BEE/COL

Ta(polycr. surf.)–H2

w82

w343

TDS

1974KO/SCH

Ta(110, surf.)–H2

10 (phys)

42

Est. by exp.

1967FEH/STI

Ta(polycr. surf.)–O2

(1) 211.8 (2) 200

886 836

(1) Calorimetry (2) Review

(1) 1960BRE/HAY (2) 1982RAO/KAM

Ta(O)x–O xZ0

1

kJ/mol

Methods (reference in parentheses)

7366—CHAPTER 15—3/2/2007—08:24—SHANMUGAM—15371—XML MODEL B – pp. 689–712

References

BDEs of V(VG)–, Nb(NbC)–, and Ta(TaC)–X bonds

711

Ta(surf.)–N2

154.4–168.0

646–703

Calorimetry

1971YAM/OGU(b)

Ta(polycr. surf.)–N2

(1) 137.4 (2) O120

575 O502

(1) Calorimetry (2) TD

(1) 1950BEE/COL (2) 1974KO/SCH

Ta(polycr. surf.)–CO

(1) 133.8 (2) 134

560 561

Calorimetry

(1) 1960BRE/HAY(b) (2) 1965BRE/HAY

Ta(polycr. surf.)–CO2

(1) 180 (2) 168 (3) 182

753 703 761

(1) Calorimetry (2) Review (3) Calorimetry

(1) 1960BRE/HAY(b) (2) Review (3) 1965BRE/HAY

Ta(CH3)5–CH3

62.4G1.2

261G5

Review

1994NOL

Ta(polycr. surf.)–C2H4

138

577

Calorimetry

1950BEE/COL

(Me3SiCH2)4Ta– (CH2SiMe3)

44G1

184.1G8.4

Calorimetry

1997LUO/LI

(Me3SiCH2)TaZ (CHSiMe3)

126G4

527G17

Calorimetry

1997LUO/LI

15.3.2 TaC–X bonds Table 15.3.2 BDEs of TaD–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

TaC(Ta)x–Ta xZ0

(1) 159.2

666

1

(1) 153.9

644

(1) CID

(1) 1996ARM/KIC

2

(1) 177.8

744

N

(2) 186.8

782

(2) Review

(2) 1994ARM/HAL

(3) w177.6

w743

(3) Extrapolate

(3) This volume

(continued)

7366—CHAPTER 15—3/2/2007—08:24—SHANMUGAM—15371—XML MODEL B – pp. 689–712

712

Comprehensive Handbook of Chemical Bond Energies

Table 15.3.2 (continued) BDEs of TaC–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom) TaC–Fe

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 72G5

301G21

(1) Photodissociation

(2) O60

O251

(2) Ion reactions

TaC–H

54.9G1.4

230G6

Ion reactions

2002ZHA/RUE

TaC–CH

(1) 137.4G2.2

575G9

(1) GIB MS

(1) 1999ARM(c)

(1) O108.5

O454

(2) O111

O464

(2) FT-ICR

(2) 1991IRI/BEA

(3) 115.9G1.2

485G5

(3) PD

(3) 2004MET

(1) 46.8G0.7

196G3

TaC–C2H4

44

184.1

Review

1998SCH/SCH

TaC–C6H4

91G1

380.7G4.2

TOF MS

2001LEE/LIN

TaC–C6H6

60w72

251w301

FT-MS

1987HET/FRE

(1) 188G15

787G63

(1) Derived

(1) 2000SCH/SCH

(2) 189

791

(2) Derived

(2) 2000DUC/GOE

(3) 181.9

761

(3) Review

(3) 2006SCH

(1) 140

586

(3) 137.9

577

201.7

844

Review

2006SCH

–CH2

–CH3

1987HET/FRE

TaC(O)x–O xZ0

1

TaC–O2

7366—CHAPTER 15—3/2/2007—08:24—SHANMUGAM—15371—XML MODEL B – pp. 689–712

chapter sixteen

BDEs of Cr(Cr G )–, Mo(Mo G )–, and W(WG)–X bonds 16.1 CrK, CrC–, and CrK–X bonds 16.1.1 Cr–X bonds Table 16.1.1 BDEs of Cr–X Bonds

The broken bonds (boldfaceZdissociated atom or group) Cr–Cr

Cr(Cr)x–Cr xZ3 4 5 6 7 8 9 10 11 12 13 14 15 16

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

(1) (2) (3) (4) (5)

34.1G1.2 40.8 33.7G2.3 39.2 36.3G1.4

142.9G5 171 141G10 163.9 152.0G6

(1) (2) (3) (4) (5)

MS Photodisso CID Review PI

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1)

38.7G3.2 46.8G3.2 52.6G3.5 57.2G3.9 53.5G2.8 55.6G3.9 57.7G3.9 63.4G5.5 66.0G5.8 69.6G5.8 66.4G7.4 61.6G7.8 64.3G9.0 49.6G9.5

161.9G13.5 (1) Derived 195.9G13.5 212.0G14.5 239.3G16.4 223.8G11.6 232.5G16.4 241.4G16.4 265.3G23.2 275.9G24.1 291.4G24.1 277.9G30.9 257.6G32.8 269.2G37.6 207.4G39.6

References (1) (2) (3) (4) (5)

1987HIL/RUT 1991LES/ASH 1993SU/HAL 1996SMI/YAT 1998SIM/LEB

(1) 2003KNI

(continued)

713

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

714

Comprehensive Handbook of Chemical Bond Energies

Table 16.1.1 (continued) BDEs of Cr–X Bonds

The broken bonds (boldfaceZdissociated atom or group) 17 18 19 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) This volume

(1) (1) (1) (2)

56.0G8.3 71.5G8.5 62.3G10.4 w82.2

234.5G34.7 299.1G35.7 260.5G43.4 w344 (2) Extrapolate

(1) (1) (2) (3) (4) (5)

15.8G0.4 14.8G0.4 21.3G0.7 14.7 14.7 15.3G0.6

66.1G1.7 61.9G1.7 89.1G2.9 61.5 61.5 64.0G2.5

Equilibrium

(1) (2) (3) (4)

18.3G0.6 14.7 14.7 14.2G0.4

76.6G2.5 61.5 61.5 59.4G1.7

RCr–CrR bond RZ(h5-C5H5)(CO)2 (P(OMe)3)

(1) 18.8G0.4 (2) 11.7

RCr–CrR bonds, RZFv(CO)3, FvZfulvalene

RCr–CrR bond RZ(h5-C5H5)(CO)3

(1) 1988MCL (2) (3) (4) (5)

1991GOH/LIM 1992WAT/JAE 1999VOL/CAM 1999WOS/NI

Equilibrium

(1) (2) (3) (4)

1990GOH/KHO 1992WAT/JAE 1999VOL/CAM 1999WOS/NI

78.7G1.7 49.0

Equilibrium

(1) 1991GOH/LIM (2) 1992WAT/JAE

16.5

69.0

Equilibrium

1999VOL/CAM

RCr–CrR bond RZ(h5-C5H5)(CO)2(PEt3) (h5-C5H5)(CO)2(PPh3)

!8 !8

!34 !34

Equilibrium

1992WAT/JAE

Cr–Nb

70.68G0.01

295.72G 0.06

Spectrometry

2000SIC/LAN

RCr–CrR bond RZ(h5-C5Me5)(CO)3

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

715

Cr–Fe

w18

w75

Cr–Cu

(1) 36.9G6 (2) 37.8G3.5

154.4G25.1 (1) MS 158.2G14.5 (2) Review

(1) 1970KAN/STR (2) 1986MOR

Cr–Au

(1) 50.5G1.5 (2) 53.5G6.9

211.3G6.5 Review 223.7G28.9

(1) 1970DAR (2) 1986MOR

[Cr(CO)3(h5-C5Me5)]2–Hg [Cr(CO)3(h5-C5Me5)]–Hg

14.7 26.6

61.5 111.3

Equilibrium

1992WAT/JAE

Cr–Al

53.3G0.2

222.9G0.9

Spectrometry

2001FU/RUS

(h5-C5H5)(CO)3Cr–GeMe3 –SnMe3

46.7G2.3 53.5G2.3

195.4G9.6 223.8G9.6

MS

1971LAP/CAR

Cr(CO)5–Xe

9.0G0.9

37.7G3.8

Transient IR

1992WEL/WEI

Cr–H

(1) (2) (3) (4)

41.8G3 41.2G3 45.4G1.6 53.0

174.9G12.6 172G13 189.9G6.8 221.8

(1) Ion reactions (2) Ion reactions (3) GIB MS (4) Spectroscopy

(1) (2) (3) (4)

(1) (2) (1) (2) (1) (2)

59.8G1 59.8 59.9G1 60.0 62.7G1 62.6

250.2G4.2 250 250.6G4.2 251 262.3G4.2 262

(1) Calorimetry (2) Review

(1) 1990KIS/ZHA (2) 2001TIL

(1) 61.5G1 (2) 62

257.3G4.2 259

(1) Calorimetry (2) Electrochem.

(1) 1990KIS/ZHA (2) 1989TIL/PAK

(CO)2R(h5-C5H5)Cr–H RZ(PPh3) (PEt3) (P(OMe)3)

RCr(CO)3–H RZ(h5-C5H5)

Spectroscopy

2003LU/ZHA

1983SAL/LAN 1985SAL/LAN 1993CHE/CLE 1995RAJ/KAR

(continued)

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

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Comprehensive Handbook of Chemical Bond Energies

Table 16.1.1 (continued) BDEs of Cr–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

(3) Review

(3) 2001TIL

(4) Kinetics

(4) 2003TAN/PAP

!51.4

!215

Electrochem.

1999TIL

!50.7

!212

Cr(polycs. surf.)–H

75

314

Review

1979TOY/SOM

Cr–F

(1) 106.4G3.5 445.2G14.5 MS (2) 125.0G4.6 523G19

(1) 1965KEN/MAR (2) 1991BOL/BOR

Cr–Cl

90.3G1.6

377.8G6.7

1995HIL

Cr–Br

78.4G5.8

328.0G24.3 Review

1968GAY

Cr–I

68.6G5.8

287.0G24.3 Review

1968GAY

Cr(O)x–O xZ0

(1) (2) (3) (4)

464G8 461G8.7 437G6 459

(1) (2) (3) (4)

(h5-C5Ph5)

(L)Cr(CO)3–H LZhydridotris(pyrazol)borate Zhydridotris(3,5dimethylpyrazolyl) borate

61.4 62.3G1 62.4 59.6

References

257 260.7G4.2 261 249.4

(h5-C5Me5)

(3) (1) (3) (4)

kJ/mol

Methods (reference in parentheses)

110.9G2 110.2G2.1 104.4G1.4 109.6

(5) 100.9G2.1 422.2G8.7 1 2

(4) 122.6 (4) 111.6

MS

(1) Ion beam (2) Mol. beam (3) Review (4) Der. from DfH0 in ref. (5) Spectroscopy

513 467

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

1986KAN/BEA(b) 1996HED/NAU 1996ARM/KIC 1998CHA

(5) 1999RED/AHA

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

717

Cr–S

79

331

MS

1967DRO/PAT

Cr–N

90.3G4.5

377.8G18.8 MS

1973SRI/FAR

Cr–Ge

(1) 39.6G7 (2) 36.8G1.7

165.7G29.3 MS 154G7

(1) 1968KAN/STR (2) 1989KIL/RUT

Cr–Sn

33.7G0.6

141G3

MS

1989KIL/RUT

Cr–Pb

25.1G0.5

105G2

MS

1989KIL/RUT

Cr(CO)5–H2

(1) 15.0G1.3 (2) 18.6G1

62.8G5.4 78G4

(1) Kinetics (2) PAC

(1) 1994WEL/HOU (2) 1995WAL/POP

(P(C6H11)3)2(CO)3Cr–H2

7.3G0.1

30.5G0.4

Calorimetry

1991ZHA/GON

(h6-C6H6)(CO)3Cr–H2

60G4

251G17

PAC

1996WAL/GEO

Cr(polycr. surf.)–H2

w45

w188

Calorimetry

1950BEE/COL

Cr–O2

113G13

473G54

Kinetics

1990PAR/MIT

Cr(O)5–O2

30.7G3.5

128G15

CID

1992HOP/MCM

Cr(polycr. surf.)–O2

(1) 173.8 (2) 180

727 752

(1) Calorimetry (2) Review

(1) 1960BRE/HAY (2) 1982RAO/KAM

Cr(CO)5–N2

19.4G1

81G4

PAC

1995WAL/POP (continued)

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718

Comprehensive Handbook of Chemical Bond Energies

Table 16.1.1 (continued) BDEs of Cr–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(P(C6H11)3)2(CO)3Cr–N2

9.3G0.2

38.9G0.8

Calorimetry

1991ZHA/GON

(h6-C6H6)(CO)3Cr–N2

66G4

276G17

PAC

1996WAL/GEO

(h5-C5Me5)(CO)3Cr–NO

w70

w293

Derived

1999CAP/BAU

Cr–OH

(1) 89.1G3.3 (2) 90

372.7G14 377

Derived

(1) 1990GOR/MIL (2) 1994HIL/LAU(b)

Cr–OD

90.2G3.3

377.2G14

Derived

1990GOR/MIL

(CrO)–H

83.5G3.5

349.4G14.6 Derived

This volume

(h5-C5Me5)(CO)3Cr–SH

46

193

Derived

1999BAU/CAP

Cr(CO)3–CO

(1) 20G15 (2) 39

84G63 163

(1) Mol. beam (2) LP

(1) 1990VEN/HOU (2) 1991RAY/ISH

Cr(CO)4–CO

(1) (2) (3) (4)

25G5 40G15 w37 33

104.6G21 167G63 w155 138

(1) (2) (3) (4)

(1) (2) (3) (4)

Cr(CO)5–CO

(1) 37G5 (2) 36.8G2 (3) 27.0

154.8G21 154.0G8.4 113.0

(1) PAC (2) LP (3) PAC

(1) 1983BER/SIM (2) 1984LEW/GOL (3) 1986YAN/PET

(h5-C5H5)Cr(CO)2–CO

w45

w188

Derived

1992BUR

Cr2O3(polycs. surf.)–CO

28

117

Review

1964HAY/TRA

Kinetics Mol. beam LP LP

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

1988FLE/ROS 1990VEN/HOU 1990ISH/BRO 1991RAY/ISH

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

719

Cr(CO)5–CS

58.2G4

244G17

MS

1980MIC/FLE

Cr–C2

107.8

451

Review

1990SIM/BEA

Cr(polycr. surf.)–CO2

(1) 81 (2) 115

339 481

(1) Review (2) Calorimetry

(1) 1964HAY/TRA (2) 1996VER

Cr–CH3

(1) 37.9G2 (2) 33.4G1.6

158.6G8.4 140G7

GIB MS

(1) 1992FIS/ARM (2) 1996ARM/KIC

Cr(CO)5–CH4

w8G2

w33.5G8

Kinetics

1994WEL/HOU

(h5-C5Me5)(CO)3 Cr–S(alkyl) –S(aryl)

43G3 35G3

180G13 146G13

Derived

1997JU/CAP

Cr(CO)5–CCl4

19.5

81.6

Derived

1992BUR

Cr(CO)5–CH3CN

(1) 28.2 (2) 21.6 (3) 31.2G2.4

118.0 90.4 130.5G10

(1) Review (2) PAC (3) PAC

(1) 1992HOF (2) 1986YAN/PET (3) 2000FAR/BUR

Cr(CO)5–C2H4

(1) 24.7G2.4 (2) 25.1G1 (3) 24.0G0.3

103.3G10.0 Kinetics 105G4 100.4G1.3

(1) 1994WEL/HOU (2) 1994MCN/BEC (3) 1995MCN/TOW

Cr(polycr. surf.)–C2H4

w100.9

w422

Calorimetry

1950BEE/COL

Cr(CO)5–C2F4

19.7G1.4

82.4G5.9

Kinetics

1994WEL/HOU

Cr(CO)5–C2Cl4

12.8G1.6

53.6G6.7

IR

2001CED/WEI (continued)

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720

Comprehensive Handbook of Chemical Bond Energies

Table 16.1.1 (continued) BDEs of Cr–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Cr(CO)5–C3H6 –1-C4H8 –cis-2-C4H8 –trans-2-C4H8 –i-C4H8 –2-Me-2-C4H8

24.2G0.3 24.2G0.3 24.8G0.3 24.6G0.3 24.1G0.3 24.5G0.4

101.3G1.3 101.3G1.3 103.8G1.3 102.9G1.3 100.8G1.3 102.5G1.7

Kinetics

1995MCN/TOW

Cr(CO)5–CH2ClCH2Cl

15.6

65.3

Derived

1992BUR

Cr(CO)5–CH3C(O)CH3

23.5

98.3

Review

1992HOF

(1) 18.2 (2) 22.4 –2,2-dimethy-THF (2) 20.8 THFZtetrahydrofuran

76.1 93.7 87.0

(1) PAC (2) Review

(1) 1986YAN/PET (2) 1992HOF

Cr(CO)5–nC5H12

8.9G3.2

37.2G13.4

PAC

1989MOR/PAR

Cr(CO)5–(Me2CCMe2)

19.6

82.0

Review

1992HOF

Cr(CO)5–(tBuCHaCH2)

20.1G1.7

84.1G7.1

IR

2002CED/WEI

Cr(CO)5–1-C6H12

22.2

92.9

Review

1992HOF

Cr(CO)5–nC7H16

(1) (2) (3) (4)

40.2G9.6 48.5 57G4 41.0G9.2

(1) (2) (3) (4)

(1) (2) (3) (4)

Cr(CO)5–THF

9.6G2.3 11.6 13.6G1 9.8G2.2

PAC Derived PAC PAC

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

1989MOR/PAR 1992BUR 1995WAL/POP 2000FAR/BUR

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

721

(h5-C5H5)Cr(CO)2–nC7H16

12

50

Derived

1992BUR

(h6-C6H6)(CO)3Cr–nC7H16

(1) 44 (2) 45

184 188

PAC

(1) 1995WAL/POP (2) 1996WAL/GEO

Cr(CO)5–nC6H14

10.8

45.2

Derived

1992BUR

Cr(CO)5–c-C6H12 –i-C8H18

12.6G2.1 11.0G2.1

52.7G8.8 46.0G8.8

PAC

1989MOR/PAR

Cr(CO)5–cis-cycloocten –trans-cycloocten

24.3 29.5

101.7 123.4

Review

1992HOF

Cr(CO)5–n-butylamine –di-n-butylamine –tri-n-butylamine

30.6 26.7 22.3

128.0 111.7 93.3

Derived

1992BUR

Cr(CO)5–piperidine

(1) 34.8 (2) 26.6

145.6 111.3

Derived

(1) 1984LEW/GOL (2) 1992BUR

Cr(CO)5–pyridine

30.1

125.9

Derived

1984LEW/GOL

(P(C6H11)3)2(CO)3 Cr–pyridine

11.2G1.6

46.9G6.7

Calorimetry

1991ZHA/GON

Cr(CO)5–2-picoline –2,6-lutidine –PBu3

27.8 25.5 31.6

116.3 106.7 132.2

Review

1992HOF

Cr(CO)5–pyrazine –pyrazole

20.8 35.8

87.0 149.8

Review

1992HOF

Cr(CO)5–HSiEt3 (h5-C6H6)Cr(CO)2–HSiEt3

22.3 28.0

93.3 117.2

Derived

1992BUR (continued)

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722

Comprehensive Handbook of Chemical Bond Energies

Table 16.1.1 (continued) BDEs of Cr–X Bonds

The broken bonds (boldfaceZdissociated atom or group) Cr(C6H6)x–C6H6 xZ0

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 1.4G3.7 (2) 2.3G1.4 (1) 64.1G3.7

5.8G15.4 PES 9.6G5.8 268.2G15.4

(1) 2002LI/BEA(b) (2) 2002LI/MCG

Cr(CO)3–C6H6

59.5G10

249.0G42

Derived from DfH0 in ref.

1996NIST

Cr(CO)5–C6H6

(1) 9.4G1 (2) 15.0 (2) 9.2G0.8 (4) 13.7G0.8 (5) O11.4 G1.1 (4) %8

39.3G4 62.8 38.5G3.3 57.3G3.3 O47.7G4.6

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

%34

(C6H6)Cr(CO)2–C6H6

O11.5G0.9

48.1G3.8

LF photolysis

2005BEN/GRU

Cr(CO)5–CF3C6H5

14.1

59.0

Derived

1992BUR

Cr(CO)3–CH3C6H5

59.5G10

249G42

1996NIST

59.5G10 56.8G10 60.4G10 49.3G10 39.8G10 55.8G10

249G42 238G42 253G42 206G42 167G42 233G42

Derived from DfH0 in ref.

30.0G3.5

125.5G14.6 Derived from DfH0 in ref.

1996NIST

1

–C6F6

–C6(CH3)6 –CH3OC6H5 –N(CH3)2C6H5 –CH3C(O)C6H5 –CH3OC(O)C6H5 –C6H5Cl

Cr(CO)3–pyridine

Kinetics Derived IR Kinetics Kinetics

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

1990ZHA/DOB 1992BUR 1993WAN/ZHE 1994WEL/HOU 2003BEN/STU

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

723

(CO)3(h5-C5Me5)Cr–SPh

(1) 35 (2) 38G3

146 159G13

Derived

(1) 1997JU/CAP (2) 2005MCD/WEI

(CO)3(h5-C5Me5)Cr–SePh –TePh

36G3 31G3

151G13 130G13

Derived

2005MCD/WEI

Cr(CO)5–P(Bu)3

21.6

90.4

PAC

1986YAN/PET

(P(C6H11)3)2(CO)3 Cr–P(OMe3)3

16.4G0.6

68.6G2.5

Calorimetry

1991ZHA/GON

16.1.2 CrC–X bonds Table 16.1.2 BDEs of CrD–X Bonds

The broken bonds (boldfaceZdissociated atom or group) CrC–Cr

CrC(Cr)x–Cr xZ1 2 3 4 5 6 7 8 9 10 11 12 13

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

(1) (2) (3) (4)

36.9G4.6 49.1 42.4 30.8

154.4G19 205.4 177.4 129

(1) (2) (3) (4)

FT-ICR PD Review Review

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1)

46.4 24.0 51.4 40.9 58.8 51.9 59.3 55.4 59.3 61.7 69.1 70.3 63.8

194 100 215 171 246 217 248 232 248 258 289 294 267

(1) Review

References (1) (2) (3) (4)

1989HOU/TUL 1991LES/ASH 1996SMI/YAT 2001ARM

(1) 2001ARM

(continued)

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

724

Comprehensive Handbook of Chemical Bond Energies

Table 16.1.2 (continued) BDEs of CrC–X Bonds

The broken bonds (boldfaceZdissociated atom or group) 14 15 16 17 18 19 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (1) (1) (1) (1) (1) (2) (3)

67.3 65.3 49.6 55.6 69.1 60.4 94.5 w82.2

kJ/mol

Methods (reference in parentheses)

References

282 273 208 233 289 253 395 w344

(2) Review (3) Extrapolate

(2) 1994ARM/HAL (3) This volume

CrC–Fe

50G7

209G29

PD

1987HET/FRE

CrC–He –Ne

1.87G0.1 2.27G0.1

7.8G0.4 9.5G0.4

Equilibrium

1991KEM/HSU

CrC(Ne)–Ne

1.8G0.2

7.5G0.8

Equilibrium

1991KEM/HSU

CrC–Ar

(1) 7.44G0.4 (2) 7.58G0.9

31.1G1.7 31.7G3.9

(1) Equilibrium (2) PD

(1) 1991KEM/HSU (2) 1991LES/ASH(b)

CrC–Xe

17.2G2.4

71.9G10.0

CID

1993KHA/CLE

CrC–H

(1) 32.5G2.1 (2) 27.7G2

136G9 116G8

(1) GIB MS (2) Review

(1) 1987ELK/ARM (2) 1987SCH/GOD

(CrO)C–H

89G5

372G21

Ion reactions

1986KAN/BEA

CrC(Cr)x–D xZ0 1 2

32.3G2.1 66.0G3.7 41.7G4.6

135G9 276G15 175G19

Ion reactions

2000CON/LIY

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BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

3 4 5 6 7 8 9 10 11 12 13

DCrC(Cr)x–D xZ8 9 10 11 12 13

(CO)6CrC–H

(L)(CO)2CrC–H LZ(h5-C5H5)(CH3)(CO) (h5-C5H5)(NO) (C6H5CH3)(CO)

725

49.5G4.2 46.4G8.5 53.3G6.9 49.3G7.3 56.2G6.5 54.4G6.9 60.2G9.9 57.0G9.0 58.1G8.8 65.5G8.5 63.0G10.4

207G17 194G36 223G29 206G31 235G27 228G29 252G42 238G38 243G37 274G36 263G43

O50.1G7.6 O38.3G9.9 O40.8G9.0 O35.1G8.8 O34.1G8.5 O36.0G10.4

O210G32 O160G41 O171G38 O147G37 O143G36 O151G43

Ion reactions

2000CON/LIY

(1) 58G3 (2) 55G2.4

243G13 230G10

(1) Thermochem. (2) Review

(1) 1981STE/BEA (2) 1990SIM/BEA

(1) (2) (1) (2) (1) (2)

255.2G17 244G22 217.6G13 207.1G14 234.3G17 220.9G15

(1) Thermochem. (2) Review

(1) 1981STE/BEA (2) 1990SIM/BEA

61G4 58.3G5.3 52G3 49.5G3.3 56G4 52.8G3.6

(CO)2(dppm)CrC–H dppmZPh2PCH2PPh2

56.0

234.3

Electrochemical

1996WAN/ANG

CrC–F

67G10

279G42

Derived from IP in ref.

1996NIST (continued)

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

726

Comprehensive Handbook of Chemical Bond Energies

Table 16.1.2 (continued) BDEs of CrC–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CrC–Cl

O50.5

O211

GIB MS

1989STR/RID

CrC–C

66.2G5.8

277G24

PI

1999QI/SHE

(CrS)C–C

66.9G6.9

280G29

CID

2001RUE/ARM(b)

CrC(H2)x–H2 xZ0 1 2 3 4 5

7.6G0.5 8.9G0.5 4.7G0.4 3.4G0.4 1.4G0.4 1.3G0.4

31.8G2.1 37.2G2.1 19.7G1.7 14.2G1.7 5.9G1.7 5.4G1.7

Equilibrium

1997KEM/WEI

(1) (2) (1) (2) (1) (2) (3)

75G8 70G7 53.8G1.9 51.6G0.9 30.2G2.3 26.2G0.9 30.3G1.7

314G33 294G29 225G7.9 216G4 126.4G9.6 110G4 126.8G7.1

GIB MS

(1) 1989GEO/ARM (2) 1996ARM/KIC

(1) (1) (2) (1) (2) (1) (2)

44G5 54.1G1.4 59.0G2.3 43.0G1.8 52G3 30.6G1.2 35.0G2.1

184G21 226G6 246.9G9.5 180G8 218G13 128G5 146.4G8.8

GIB MS

(1) R30G5 (2) 22.9G2.5 (2) 25.8G2.6

R126G21 96G11 108G11

Ion reactions

CrC–CH –CH2 –CH3

CrC–C2H2 –C2H3 –CHCH3 –C2H5

CrC(C2H4)x–C2H4 xZ0 1

(3) 1992FIS/ARM

(1) 1996ARM/KIC (2) 1992FIS/ARM

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

(1) 1996ARM/KIC (2) 1998SIE/JAR

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

727

CrðCOÞC 6 –C2 H4

14.3G1.2

59.8G5.0

HP MS

1991HOP/MCM

CrC–C3H4

(1) (2) (1) (2) (1) (2) (1) (2) (1) (2)

175.7G8.4 141G7 163G13 124G9 151G13 113G10 134.3G5.9 115G6 119.2G5.4 101G5

GIB MS

(1) 1992FIS/ARM (2) 1996ARM/KIC

–C(CH3)2 –CHCH2CH3 –n-C3H7 –i-C3H7

CrC(OH)–1-C4H8

CrC(C6H6)x–C6H6 xZ0

1

Cr +

(

Y

42G2 33.6G1.6 39G3 29.6G2.1 36G3 27.0G2.5 32.1G1.4 27.5G1.4 28.5G1.3 24.1G1.2

75.2G4.8

314.5G20.3 CID

2005HAN/ICH

(1) (2) (3) (4) (5) (2) (4) (6)

40.4G2.3 39.2G3.5 44.5 40.6G2.4 40.1G1.2 50.7G9.2 55.4G4.4 57.9G3.5

169G10 164G14.5 186.2 170G10 167.9G4.8 212G39 232G18 242.2G14.5

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

(6) PES

(6) 2002LI/BEA(b)

(1) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2)

36.2G2.7 39.1 32.9 32.0 29.0 29.3 29.9 26.3 25.4 24.6 26.6 23.6 19.0

151G11 163.6 137.7 133.9 121.3 122.6 125.1 110.0 106.3 102.9 111.3 98.7 79.5

Kinetics

(1) 1998SCH/WES (2) 1999RYZ/YAN

FT-ICR FT-ICR FT-ICR GIB MS PES

1997LIN/CHE(b) 1997LIN/DUN 1999RYZ/YAN 2000ROD/ARM(b) 2002LI/MCG

)

YZF 1,2-difluoro 1,3-difluoro 1,4-difluoro 1,2,3-trifluoro 1,2,4-trifluoro 1,3,5-trifluoro 1,2,3,4-tetrafluoro 1,2,3,5-tetrafluoro 1,2,4,5-tetrafluoro Pentafluoro Hexafluoro

(continued)

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

728

Comprehensive Handbook of Chemical Bond Energies

Table 16.1.2 (continued) BDEs of CrC–X Bonds

The broken bonds (boldfaceZdissociated atom or group) CrC–toluene

CrC(L)x–L, LZp-xylene xZ0 1

CrC(L)x–L, LZmesitylene xZ0 1

Cr +

(

Y

(

Y

YZCl OH NH2 CN 1-F-2-methyl 1-F-3-methyl 1-F-4-methyl

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 42.2G3.5 (2) 42.6G2.4

176.6G14.5 Kinetics 178G10

(1) 1997LIN/DUN (2) 1998SCH/WES

(1) 43.1G4.6 (2) 44.3G2.5 (1) 50.7G6.9

180.4G19 185G10 212G29

Kinetics

(1) 1997LIN/DUN (2) 1998SCH/WES

(1) 46.1G6.9 (2) 45.9G2.6

193G29 192G11

Kinetics

(1) 1997LIN/DUN (2) 1998SCH/WES

43.5G2.4 44.3G2.5 44.3G2.5 45.7G2.6 47.1G2.7 48.2G2.7 49.0G2.8

182G10 185G10 185G10 191G11 197G11 202G11 205G12

Kinetics

1998SCH/WES

(1) (1) (2) (1) (1) (1) (1) (1)

155G11 (1) Kinetics 172G10 179.9G16.7 (2) Combined 184G12 197G13 162G10 161G10 161G10

)

YZEt 1,2-dimethyl 1,3-dimethyl 1,2,4-trimethyl 1,2,4,5-tetramethyl Pentamethyl Hexamethyl

Cr +

BDEs (boldfaceZ recommended data; reference in parentheses)

)

37.1G2.9 41.0G2.5 43G4 44.8G2.9 47.0G3.2 38.8G2.5 38.5G2.5 38.5G2.7

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

(1) 1998SCH/WES (2) 1999RYZ/DUN

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

729

CrC–indole

47G4

196.6G16.7 Combined

1999RYZ/DUN

CrC–O

(1) 40–119 (2) 85.8

167–498 359

(1) ICR (2) Review

(1) 1981KAP/STA (2) 2001ARM

129.5 139.6 159.9 147.0 147.9 148.7 155.8 150.1 154.9 149.1 151.1 156.8 146.0 145.8 137.9 122.4

542 584 669 615 619 622 652 628 648 624 632 656 611 610 577 512

Review

2001ARM

(1) 83G2 (2) 77 (3) 66

347G8 322 276

(1) Ion reactions (2) Derived (3) Ion reactions

(1) 1982ARM/HAL (2) 1991IRI/BEA (3) 1996FIE/KRE

267.4 278.9 313.6 309.0 325.0 320.5 316.0 313.6 297.6 302.1 304.5 306.6 283.7 269.8

1119 1167 1312 1293 1360 1341 1322 1312 1245 1264 1274 1283 1187 1129

Review

2001ARM

CrC(Cr)x–O xZ1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16

CrC(O)–O

CrC x –2O xZ2 3 4 5 6 7 8 9 10 11 12 13 14 15

(continued)

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

730

Comprehensive Handbook of Chemical Bond Energies

Table 16.1.2 (continued) BDEs of CrC–X Bonds

The broken bonds (boldfaceZdissociated atom or group) CrC(C)–CO

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

34.6G9.2

145G39

TOF MS

1997QI/YAN

(1) 30.7 (2) 21.9G0.9 (3) 21.4G1.4 (4) O10.8 (1) 35.1 (2) 22.6G0.7 (3) 44.3G1.4 (4) %30.0G 3.9 (1) 26.7 (2) 13.6G1.4 (3) 15.0G1.2 (4) 16.1G3.2 (1) 20.8 (2) 13.6G1.4 (3) 17.8G0.9 (4) 16.1G2.3 (1) 13.8 (2) 15.2G0.7 (3) 12.9G0.7 (4) 12.2G13.8 (1) 33.0 (2) 32.3G1.8 (3) 27.4G0.5 (4) 32.1G2.1 (5) 33.0G2.1

128.3 91.7G3.9 89.7G5.8 O45.3 146.7 94.6G2.9 185.2G5.8 %125.4G 16.4 111.9 56.9G5.8 62.7G4.8 67.5G13.5 86.8 56.9G5.8 74.3G3.9 67.5G9.6 57.9 63.7G2.9 54.0G2.9 51.2G57.9 138.0 135.1G7.7 114.8G1.9 134.1G4.8 138.0G8.7

(1) (2) (3) (4)

(1) (2) (3) (4)

(C5H5)(GeMe3)CrC (CO)x–CO xZ0 1 2

24.0 9.2 30.9

(C6H6)CrC(CO)x–CO xZ0

24.0G1.2

CrC(CO)x–CO xZ0

1

2

3

4

5

MS CID PI PIE

1980MIC/FLE 1993KHA/CLE 1997QI/YAN(b) 1997CHE/LIA

(5) CID

(5) 2001MUN/ARM

100.3 38.6 129.3

MS

1971CAR/KEP

100.3G4.8

PES

2002LI/MCG

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

1 2

CrC–OH

CrC(H2O)x–H2O xZ0

1 2 3 N

731

13.8G1.2 23.8G1.2

57.9G4.8 99.4G4.8

(1) (2) (3) (4)

73G5 73G5 74.3 71.3G3.3

305G21 305G21 311 298G14

Ion reactions

(1) (2) (3) (4)

(1) (2) (3) (1) (3) (3) (3) (4)

21.9 29.0 31.7G2.1 29.5 34.0G1.8 12.1G1.2 12.1G1.4 w10.5

91.6 121.3 132.6G8.8 123.4 142.3G7.5 50.6G5.0 50.6G5.8 w44

CID

(1) 1989MAR/SQU (2) 1989MAG/DAV(b) (3) 1994DAL/HON

(4) Extrapolate

(4) This volume

1986KAN/BEA 1989MAG/DAV 1989MAG/DAV(b) 1996ARM/KIC

CrC–OC(CH3)2 –OC(CD3)2

42.0G3.5 37.4G3.5

176G14 156G14

FT-ICR

1997LIN/CHE

CrC–furan

27

113

FT-ICR

2004GRI/MAN

CrC–S

61.8G3.9

258.6G16.4 CID

2001RUE/ARM

CrC–CS

39.0G1.4

163.1G5.8

CID

2001RUE/ARM(b)

CrC–N2

14.1G0.9

59G4

Photodisso.

1991LES/ASH(b)

CrC–NH2

65.1G2.3

272G10

Review

1996ARM/KIC

(1) 37 (2) 43.7G2.4 (1) 40.8

154.8 183G10 170.7

CID

(1) 1989MAR/SQU (2) 1998WAL/ARM

CrC(NH3)x–NH3 xZ0 1

(continued)

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

732

Comprehensive Handbook of Chemical Bond Energies

Table 16.1.2 (continued) BDEs of CrC–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 42.8G2.2 (2) 12.9G1.4 (2) 7.2G2.2

179G9 54G6 30G9

CrC–pyridine –pyrimidine

47.4G2.7 42.7G1.5

198.4G11.3 CID 178.8G6.4

2000ROD/STA 2001AMU/ROD

CrC(L)x–L, LZpyrrole xZ0 1

42.5 34.9

177.8 146.0

Kinetics

2000GAP/YAN

CrC–adenine

56.0G1.9

234G8

CID

2002ROD/ARM

CrC–imidazole

52.5G1.3

219.8G5.5

CID

2004RAN/AMU

CrC–Si –SiH –SiH2 –SiH3

48.4G3.7 23.5G6.7 22.8G3.2 18.0G4.1

203G15 98G28 95G13 75G17

CID

1994KIC/ARM

CrC2(CO)x–CO xZ0 1 2

79.8G5.8 69.2G12.7 41.5G10.4

334G24 290G53 174G43

PI

1997QI/YAN(b)

(C5H5)CrC(CO)3–GeMe3

29.3

122.5

MS

1971CAR/KEP

2 3

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

733

16.1.3 CrK–X bonds Table 16.1.3 BDEs of CrL–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CrK–Cr

4.8G0.2

20.1G1.0

PES

1993CAS/LEO

CrK–H

50.9G3.8

213G16

Derived

1991ARM/SUN

CrK(CO)5–Cl –Br –I

79.2 70.6 57.2

331.4 295.4 239.3

Kinetics

1989JON/MCD

CrK(O)x–O xZ0

144.9G8

606G33

1996NIST

105.7G9 166.2G9 69G10

442G37 695G37 289G37

Derived from DfH0 in ref.

CrK(O)5–O2

30.7G3.5

128.3G14.6

CID

1992HOP/MCM

CrK(CO)x–CO xZ0

(1) 20

83.7

(1) Neg. ion resonance

(1) 1965PIG/FOF

(1) (1) (2) (3) (1) (2) (3) (1) (2) (3) (4)

146.4 146.4 187.0G11.7 184G16 230.1 176.6G17.6 166G16 R50 182.4G10.5 170G15 187.0G14.6

(2) CID (3) CID

(2) 1992SUN/SQU (3) 1993SUN/WAN

(4) FTICR

(4) 1992HOP/MCM

1 2 3

1 2

3

4

35 35 44.7G2.8 43.9G3.9 55 42.2G4.2 39.7G3.9 R12 43.6G2.5 40.6G3.5 44.7G3.5

(continued)

7366—CHAPTER 16—3/2/2007—10:52—CRCPAG—15372—XML MODEL B – pp. 713–780

734

Comprehensive Handbook of Chemical Bond Energies

Table 16.1.3 (continued) BDEs of CrK–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(L)(CO)3CrK–CO LZO (CO)2

38.0G3.5 44.7G3.5

159G15 187G15

CID

1992HOP/MCM

(h5-C5H5)CrK(CO)2–CO

47.8G4.3

200G18

CID

1999SUN/SQU

CrK(CO)5–CHO

(1) %35.1 (2) %32

%147 %134

Review

(1) 1990SIM/BEA (2) 2004DAM

CrK(CO)3(O)2–(CO)2

28.1G2.3

117.6G10

CID

1992HOP/MCM

16.2 MoK, MoC–, and MoK–X bonds 16.2.1 Mo–X bonds Table 16.2.1 BDEs of Mo–X Bonds

The broken bonds (boldfaceZdissociated atom or group) Mo–Mo

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 97G5 (2) 95.4 (3) 104.1G0.2

406G21 399.3 435.5G1.0

(1) MS (2) Review (3) PI

(1) 1978GUP/ATK (2) 1996SMI/YAT (3) 1998SIM/LEB

R(CO)3Mo–Mo(CO)3R RZO–i–Pr h5-C5H5

(1) w44 (2) 32.5G0.5

w184 136G2

Derived

(1) 1981CAV/CON (2) 1986NOL/VEG

(MoO3)–MoO3

110G10

460G42

Review

1967DRO/GOL

Mo–Mo bond in [Mo2(m-OH)2]4C

12.4G1.9

52G8

Calorimetry

2003PRO/DEM

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

735

Mo(polysc. surf.)–Li –Na –K –Rb –Cs

72.4 60.0 58.3 53.3 48.4

303.0 250.9 244.1 222.9 202.6

TDS

1971SCH/KLE

Mo(100, surf.)–Ba

95.6

400

FIM

1972BON/KON

Mo(110, surf.)–Ba

16 (phys)

67

Review

1995SEE/ALL

Mo(110, surf.)–Ba

(1) 87.5 (2) 115

366 481

(1) FIM (2) Review

(1) 1972BON/KON (2) 1995SEE/ALL

Mo–Nb

108G6

452G25

Review

1986MOR

Mo(110, surf.)–Fe

2.3G1.2 (phys)

9.6G4.8

PLD

2003JUB/FRU

Mo(110, surf.)–Rh

14.3G1.4 (phys) 60G6

FIM

1990DHA/BAS

Mo(110, surf.)–Rh

140

586

Review

1995SEE/ALL

Mo(110, surf.)–Rh2

15.0

62.7

FIM

1990DHA/BAS

Mo(polysc. surf.)–Cu

12.5 (phys)

52

SIE

1970ABR/SLE

Mo(polysc. surf.)–Cu

92

385

Review

1995SEE/ALL

Mo(polysc. surf.)–Ag

(1) 35 (2) 43.8G6.9

146 TDS 183.3G28.9

(1) 1958PTU (2) 1963GOE/PEA

Mo(polysc. surf.)–Au

96.9G4.6

405.2G19.3 Radio

1963GOE/LUC (continued)

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

736

Comprehensive Handbook of Chemical Bond Energies

Table 16.2.1 (continued) BDEs of Mo–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Mo(polysc. surf.)–Hg

44.3G4.2

185.2G17.4 TDS

1968SWA/STR

Mo(110, surf.)–Ga

5.8 (phys)

24.1

FIM

1994SAA

Mo(110, surf.)–Ga

60

251

Review

1995SEE/ALL

Mo(110, surf.)–In

6.9 (phys)

28.9

FIM

1994SAA

(h5-C5H5)(CO)3Mo– GeMe3 –SnMe3

60.0 71.0

250.9 297.2

Derived

1991CAR/KEP

Mo(110, surf.)–Sn

11.5 (phys)

48.2

FIM

1994SAA

Mo(100, surf.)–Pb

80.2

335.4

Calorimetry

1997STU/STA

Mo(CO)5–Xe

8.0G1.0

33.5G4.2

Transient IR

1992WEL/WEI

Mo–H

(1) 46.0G3 (2) 53G5 (3) 50.4G4.5

193G13 222G21 211G19

Ion reactions

(1) 1985SAL/LAN (2) 1986TOL/BEA (3) 1991ARM/SUN

Mo(polycs. surf.)–H

14.8G0.2 (phys) 61.9G0.8

Kinetics

1981PIC

Mo(100, surf.)–H

66

276

Review

1991BEN

Mo(110, surf.)–H

34

142.3

FDMS

1972MAH/SCH

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

(L)Mo(CO)3–H LZ(h5-C5H5)

(h5-C5Me5)

(L)Mo(CO)3–H LZhydridotris(pyrazol)borate hydridotris(3,5-dimethylpyrazolyl)borate

Mo(H)x(h5–C5H5)2–H xZ0 1

Mo(F)x–F xZ0 1 2 3 4 5

(1) (2) (3) (4) (5) (3) (4) (5) (6) (7)

66G8 67.4G1.4 69.2 65.2G2.2 69.3 68.5 69 68.6 70 66

737

276G34 282.0G6 289.5 272.8G9.2 290 286.6 289 287 293 276

(1) (2) (3) (4) (5)

(6) Electrochem. (7) Derived

(6) 1991EIS/LAW (7) 1992HOF

62.1

260

Electrochemical

1993SKA/TIL

59.3

248

(1) (1) (2) (3)

246 268 251G8 256.9G8.4

(1) Derived

(1) 1988DIA/SIM

(2) Calorimetry (3) Review

(2) 1987CAL/DIA (3) 1994NOL

58.8 64.1 60.0G1.9 61.4G2.0

Calorimetry Review Electrochem. Review Review

(1) (2) (3) (4) (5)

1985HOF 1990SIM/BEA 1991PAR/HAN 1994NOL 2001TIL

111 124 120 105 88 94

464 519 502 439 368 392

MS

1976HIL

Mo(polycs. surf.)–F

(1) 107 (2) 103.8G3.5

449 434G14

(1) MS (2) Ion beam

(1) 1972SCH/KLE (2) 1979BOL/BLA

Mo(100, surf.)–F

106.1G2.3

443.8G9.6

Ion beam

1981BOL/BLA

Mo(110, surf.)–F

106.1G2.3

443.8G9.6

Ion beam

1983BOL/BLA (continued)

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

738

Comprehensive Handbook of Chemical Bond Energies

Table 16.2.1 (continued) BDEs of Mo–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Mo(111, surf.)–F

w107.2

w449

Ion beam

1981BOL/BLA

Mo(Cl)x–Cl xZ4 5

44.0 27.0

184 113

Derived from DfH0 in ref.

1996NIST

Mo(Cl)x(h5-C5H5)2–Cl xZ0 1

56.9 88.2

238 369

Derived

1988DIA/SIM

Mo(CO)3(h5-C5H5)–Cl

72.4G0.9

302.9G3.8

Derived

1986NOL/VEG

Mo(polycs. surf.)–Cl

(1) 95 (2) 87.6G3.5

397 367G14

(1) MS (2) Ion beam

(1) 1972SCH/KLE (2) 1979BOL/BLA

Mo(100, surf.)–Cl

95

397

Review

1974ERT

Mo(110, surf.)–Cl

w95.7

400

Ion beam

(2) 1981BOL/BLA

Mo(111, surf.)–Cl

w95.7

400

Ion beam

1981BOL/BLA

Mo(Br)x–Br xZ0 1 2 3

74.9 96.0 68.7 65.6

313.4 401.7 287.4 274.5

Derived from DfH0 in ref.

1996NIST

Mo(CO)3(h5-C5H5)–Br

60.5G2.0

253.1G8.4

Derived

1986NOL/VEG

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

739

Mo(polycs. surf.)–Br

(1) 85 (2) 64.6G3.5

357 270G14

(1) MS (2) Ion beam

(1) 1972SCH/KLE (2) 1979BOL/BLA

Mo(100, surf.)–Br

w84.1

w352

Ion beam

1981BOL/BLA

Mo(111, surf.)–Br

w84.1

w352

Ion beam

1981BOL/BLA

Mo(I)x–I xZ0 1 2 3

63.8 83.1 43.4 39.4

266.9 347.7 181.6 164.8

Derived from DfH0 in ref.

1996NIST

Mo(CO)3(h5-C5H5)–I

51.8G1.0

216.7G4.2

Derived

1986NOL/VEG

Mo(polycs. surf.)–I

73

304

MS

1972SCH/KLE

Mo(O)x–O xZ0

(1) 142.7G8.0

597.2G33.5 (1) Derived from DfH0 in ref. 524.9G3.9 (2) Derived 502 (3) ICR 568.5G35.8 661 587.3G24.4 598

1 2

(2) (3) (1) (3) (1) (3)

125.4G0.9 120 135.9G8.6 158 140.4G5.8 143

(1) 1996NIST (2) 2000SIM/MIT (3) 2002GON/FIA

O3MoMo(O2)–O (O3Mo)2Mo(O2)–O

104 53

435 222

ICR

2002GON/FIA

(Et2NCS2)2Mo–O 2(Et2NCS2)2Mo–O

96.0 101.0

401.7 422.6

Calorimetry

1977WAT/MCD

Mo(100, surf.)–O

17 (phys)

71

FEM

1993SON/GOM (continued)

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

740

Comprehensive Handbook of Chemical Bond Energies

Table 16.2.1 (continued) BDEs of Mo–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Mo(100, surf.)–O

118

494

TD

1969VAS/PTU

(h5-C5Me5)2Mo–O (h5-C5Me5)2MoaO

65 111

272 464

Derived

1998LUO/LAN

Mo(100, surf.)–O

117.6

492

TD

1968VAS/PTU

(NRAr)3Mo–N RZt-Bu or C(CD3)2CH3

155.3G3.3

649.8G13.8 Derived

2001CHE/JOH

Mo(100, surf.)–N Mo(110, surf.)–N

156 153

653 640

Review

1991BEN

(ArR[Bu]N)3Mo–P RZt-Bu

92.2

385.8

Derived

2005STE/JOH

Mo–C

(1) (2) (1) (2)

478G16 482G16 494G22 500

(1) MS (2) Review

(1) 1981GUP/GIN (2) 1990SIM/BEA

–C2

114.2G3.8 115.2G3.8 118.1G5.4 119.5

Mo(CO)5–H2

19.4G1

81G4

PAC

1995WAL/POP

(P(C6H11)3)2(CO)3Mo–H2

6.5G0.2

27.2G0.8

Calorimetry

1991ZHA/GON

Mo(polycr. surf.)–H2

28 (phys)

117

TD

1974KO/SCH

Mo(polycr. surf.)–H2

40

167

Calorimetry

1966CER/PON

Mo(100, surf.)–H2

16G2 (b1-state) 67G8

FD MS

1971HAN/SCH

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

741

20G2 (b2-state) 84G8 27G2 (b3-state) 113G8

Mo(polycr. surf.)–O2

(1) (2) (3) (4) (5)

Mo(CO)5–N2

171 172 104 132 130

715 720 435 552 544

(1) (2) (3) (4) (5)

19.6G1

82G4

PAC

1995WAL/POP

(P(C6H11)3)2(CO)3Mo–N2

9.0G0.6

37.7G2.5

Calorimetry

1991ZHA/GON

Mo(polycs. surf.)–N2

6–20 (phys)

25–84

TD

1968KIN/TOM

Mo(polycs. surf.)–N2

(1) (1) (2) (3)

265 299 253G8 w335

TD

(1) 1964OGU

63.4 71.5 60.5G2 w80

Calorimetry Calorimetry Calorimetry TD Review

(1) (2) (3) (4) (5)

1960BRE/HAY 1965BRE/HAY 1966BRE/GRA 1968GRE/STI 1982RAO/KAM

(2) 1967PAR/PRY (3) 1974KO/SCH

Mo(100, surf.)–N2

9.7G1 (phys)

40.6G4.2

FDMS

1971HAN/SCH

Mo(100, surf.)–N2

87G3

364G13

FDMS

1971HAN/SCH

Mo(110, surf.)–N2

81G3

339G13

TD

1972LAP/NEI

Mo(100, surf.)–NO

10.8 19.6

45 82

TPD

1990FUL/TYS

(h5-C5Me5)(CO)3Mo–SH

55

230

Derived

1999BAU/CAP (continued)

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

742

Comprehensive Handbook of Chemical Bond Energies

Table 16.2.1 (continued) BDEs of Mo–X Bonds

The broken bonds (boldfaceZdissociated atom or group) Mo(CO)x–CO xZ3

4

5

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (2) (3) (1) (3) (4) (2) (4) (5)

30G15 31G5 31 35G15 29.5 27G5 35G5 34G5 40.5G2

kJ/mol 126G63 129.7G21 130 146G63 123.4 113.0G21 146.4G21 142.3G21 169.5G8.4

Methods (reference in parentheses)

References

(1) Mol. beam (2) LP (3) LP

(1) 1990VEN/HOU (2) 1990GAN/ROS (3) 1991RAY/ISH

(4) PAC

(4) 1983BER/SIM

(5) LP

(5) 1984LEW/GOL

Mo(polycr. surf.)–CO

(1) 35 (phys) (2) 4.6 (2) 20.3

146 19.3 85

TD

(1) 1964RED (2) 1967DEG

Mo(polycr. surf.)–CO

(1) 74 (2) 65.7 (3) 74.7

310 275 313

(1) Calorimetry (2) TD (3) Tracer

(1) 1965BRE/HAY (2) 1967DEG (3) 1967CRO/MAT

Mo(100, surf.)–CO

(1) 13.8 (phys) (2) 13G1 (a1 state) (2) 23G2 (a2 state)

57.9 54.4G4

(1) PI (2) TDS

(1) 1981SEM/EST (2) 1985ZAE/KOL

(1) 65.7G0.7 (1) 70.3G0.7 (1) 74.7G0.9 (1) 77.3G0.9 (1) 81.6G1.2 (2) 62G4 (b1 state) (2) 79G4 (b2 state) (2) 86G4 (b3 state) (3) 63G2 (b1 state)

275G3 294G3 313G4 323G4 342G5 259G17

TDS

(1) 1971MAT

Mo(100, surf.)–CO

96.2G8

(2) 1973VIS/SCH

331G17 360G17 264G8

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

(3) 1985ZAE/KOL

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

743

(3) 70G2 (b2 state) (3) 93G2 (b3 state)

293G8

Mo(110, surf.)–CO

(1) 18.9G1.2 (2) w21

79.1G4.8 w87

(1) XPS (2) TPD

(1) 1986ERI/EST (2) 2003JUE/RAA

Mo(CO)5–CS

65.6G14

274G59

MS

1980MIC/FLE

Mo(polycr. surf.)–CO2

(1) 89 (2) 109

372 456

(1) Review (2) Calorimetry

(1) 1964HAY/TRA (2) 1965BRE/HAY

!9.5 14G2

!39.7 58.6G8.4

Kinetics

1994LIA/MIT

(1) 47.0G1.6 (2) 48.5G2

196.6G6.7 203G8

(1) Derived (2) Review

(1) 1988NOL/VEG (2) 1990SIM/BEA

149 202.9G7.1 183 166G8 142G8

(1) Derived (2) Review

(1) 1988DIA/SIM (2) 1994NOL

(3) Calorimetry

(3) 1987CAL/DIA

Mo(Mo)x–NH3 xZ0 1

Mo(CO)3(h5-C5H5)–CH3

Mo(CH3)x(h5-C5H5)2–CH3 xZ0 (1) (2) 1 (1) (2) (3)

35.6 48.5G1.7 43.7 39.7G1.9 33.9G1.9

389G8

Mo(polycr. surf.)–CH4

65.2

273

Calorimetry

1977SMU/CER

Mo(polycr. surf.)–C2H2

62.4

261

Calorimetry

1977CER/SMU(b)

Mo–C2H4

17G3.5

71G15

Kinetics

1994LIA/MIT (continued)

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

744

Comprehensive Handbook of Chemical Bond Energies

Table 16.2.1 (continued) BDEs of Mo–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Mo(h5-C5H5)2–C2H4

14.1G4.8

59G20

Review

1990SIM/BEA

Mo(polycr. surf.)–C2H4

69.3

290

Calorimetry

1977CER/SMU(b)

Mo(CO)3(h5-C5H5)–C2H5

(1) 37 (2) 44.2G2.6

154.8 185G11

(1) Derived (2) Review

(1) 1988NOL/VEG (2) 1990SIM/BEA

Mo(polycr. surf.)–C2H6 –C3H8

100.1 133.4

419 558

Calorimetry

1977SMU/CER

Mo(CO)3(h5-C5H5)–C3H5

35.1G2.4

147G10

Review

1990SIM/BEA

Mo(polycr. surf.)–c-C3H6

w123.6

w517

Calorimetry

1977CER/SMU

78 Mo(polycr. surf.)–C3H6 –C(CH3)2 72.4 –HCCCH3 70

328 303 293

Calorimetry

1977CER/SMU(b)

Mo(C4H9)(h5-C5H5)2 –C4H9

35.1G2.8

147G12

Review

1994NOL

Mo(110, surf.)–PhOH

42

176

TPR

1989SER/FRI

(CO)3(H)Mo–(h5-C5H5) –(h5-C5Me5)

93 91

389 381

Derived

1992HOF

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

745

Mo(CO)5–nC7H16

(1) 8.7G2.7 (2) 17.3 (3) 15.3G1

36.4G11.3 72.4 64G4

PAC

(1) 1989MOR/PAR (2) 1992BUR (3) 1995WAL/POP

Mo(CO)5–HSiEt3

27.2

113.8

PAC

1992BUR

Mo(CO)5–alkane

(1) (2) (1) (2)

46.0 56 104.6 155

(1) PAC (2) LIOAS

(1) 2001JIA/LEU (2) 2003GIT/JIA

–tetrahydrothiophene

11 13.4 25 37.0

Mo(CO)5–piperidine –pyridine

43.7 29.7

182.8 124.3

Derived

1984EW/GOL

(P(C6H11)3)2(CO)3 Mo–pyridine –P(OMe3)3

16.9G0.6 24.0G1.0

70.7G2.5 100.4G4.2

Calorimetry

1991ZHA/GON

LMo(OCl)–P(OMe3)3 LZhydrotris(3, 5-dimethyl1-pyrazol)borate

29.5G3.5

123.4G14.6 FT-ICR SID

2004NEM/LAS

Mo(CO)3(h5-C5H5) Mo–C6H5CH2

(1) 32 (2) 36.8G2.4

133.9 154G10

(1) Derived (2) Review

(1) 1988NOL/VEG (2) 1990SIM/BEA

(h5-C5H5)(CO)3 Mo–CH(CH3)C6H5

25

104.6

Thermolysis

1992MAN/HAL

(h5-C5H5)2Mo–C2(Ph)2

(1) 28.7G6.5 (2) 27.5G6.2

120G27 115G26

(1) Review (2) Calorimetry

(1) 1990SIM/BEA (2) 1993DIO/PIE

59.9G3.2

250.6G13.4 MS

(h5-C5H5)(CO)3 Mo–GeMe3

1971LAP/CAR (continued)

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746

Comprehensive Handbook of Chemical Bond Energies

Table 16.2.1 (continued) BDEs of Mo–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

kJ/mol

(h5-C5H5)(CO)3 Mo–SnMe3

71.0G2.3

297.1G9.6

(L)3Mo–CNAd LZN[i-Pr]Ar AdZ1-adamantyl

10.2

42.7

16.2.2

Methods (reference in parentheses)

Stopped-flow spectro

References

2004STE/FIG

MoC–X bonds

Table 16.2.2 BDEs of MoD–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

MoC–Mo

(1) 116.2 (2) 107.4G0.2

486 449.4G1.0

(1) Review (2) PI

(1) 1996SMI/YAT (2) 1998SIM/LEB

MoC–Xe

O12.7G1.6

O53.1G6.8

CID

1998SIE/ARM(b)

MoC–H

40.6G1.4

170G6

CID

1996SIE/CHE

MoðCOÞC 6 –H

(1) 65G3 (2) 62.1G2.2

272G13 260G9

(1) Thermochem. (2) Review

(1) 1981STE/BEA (2) 1990SIM/BEA

MoCO5–H

O104

O435

ICR

2004GON(c)

(L)(CO)2MoC–H LZ(arphos)2 arphos: Ph2P(CH2)2AsPh2

63.6

266.1

Electrochemical

1996WAN/ANG

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BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

(dppe)2 dppe: Ph2P(CH2)2PPh2 (dppm)2 dppm: Ph2P(CH2)PPh2

66.2

277.0

67.2

281.2

55.4

232

53.3

223

MoC–F

90G7

MoC–C

(L)MoC(CO)3–H LZhydridotris(pyrazol)borate hydridotris(3,5dimethyl-pyrazolyl) borate

747

Electrochemical

1993SKA/TIL

376G29

Derived from IP in ref.

1996NIST

(1) 79.8G6.9 (2) 99.4G4.6 (3) 105.8G4.4

334G29 416G19 442.7G18.3

(1) PI (2) GIB MS (3) Review

(1) 1997QI/YAN (2) 1998SIE/ARM(b) (3) 2006ARM

MoC(CO)–C

56.3G11.5

235G48

PI

1997QI/YAN

MoC–CH

(1) (2) (1) (2) (1) (2)

509G10 513.3G13.5 329G12 344.4G10 157G12 151.5G8.7

GIB MS

(1) 1999ARM(c) (2) 2006ARM

–CH2 –CH3

121.7G2.3 122.7G3.2 78.6G2.9 82.3G2.3 37.5G2.9 36.2G2.1

MoC 2 O5 –CH4 MoC 3 O8 –CH4

O89 O89

O372 O372

ICR

2004GON(c)

MoC–C2H2 –C2H4

(1) (1) (2) (1) (1)

R312 R137 104.6 R245 R251

(1) Ion beam

(1) 1988SCH/BEA(b)

(2) Review

(2) 1998SCH/SCH

–1,3-C4H8 –C6H6

R74.5 R32.7 25 R58.6 R60

(continued)

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748

Comprehensive Handbook of Chemical Bond Energies

Table 16.2.2 (continued) BDEs of MoC–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

References

kcal/mol

kJ/mol

(1) 118G2 (2) 116.7G0.5 (3) 98.5 (1) 131G5 (2) 128.4G3.2 (3) 121 (1) 62G17 (3) 83

494G8 488.2G1.9 412 548G21 537.4G13.5 506 259G71 347

(1) Re-evaluated (2) CID (3) ICR

(1) 1997KRE/FIE (2) 1998SIE/ARM(b) (3) 2002GON/FIA

O3MoMoC(O2)–O (O3Mo)2MoC(O2)–O

56 58

234 243

ICR

2002GON/FIA

MoC(O)x–CO xZ1 2

18.4G1.8 21.2G3.9

77.2G7.7 88.8G16.4

GIB MS

1998SIE/ARM(b)

(1) 57.7 (2) 39.7 (3) 46.4G2.3 (4) O11.3 (5) 10.6G3.9 (1) 43.8 (2) 39.7 (3) 45.7G1.2 (4) %38.3G 7.1 (1) 35.5 (2) 36.2 (3) 29.3G0.9 (4) 33.7G5.1 (1) 24.9 (2) 38.7 (3) 41.3G0.9 (4) 40.1G5.1

241.2 166.0 193.9G9.6 O47.3 44.4G16.4 183.3 166.0 191.0G4.8 %160.2G 29.9 148.6 151.5 122.5G2.9 140.9G21.2 104.2 162.1 172.7G2.9 167.9G21.2

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

MoC(O)x–O xZ0

1

2

MoC(CO)x–CO xZ0

1

2

3

MS MS PI PIE GIB MS

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

1965FOF/PIG 1980MIC/FLE 1997QI/YAN 1997CHE/LIA 1998SIE/ARM(b)

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

4

5

MoC(O)x–CO2 xZ0 1

MoC(S)x–S xZ0 1 2

(1) (2) (3) (4) (1) (2) (3) (4)

37.8 36.7 31.8G0.7 30.9G1.4 30.9 36.0 35.7G0.5 32.7G1.8

158.2 153.4 133.1G2.9 129.3G5.8 129.3 150.5 149.5G1.9 137.0G7.7

11.8G1.6 17.8G0.7

49.2G6.8 74.3G2.9

(1) (2) (1) (2) (1) (2)

368G59 355.1G5.8 418G59 395.6G9.6 368G59 325.1G8.7

88G14 84.9G1.4 100G14 94.5G2.3 88G14 77.7G2.1

749

GIB MS

(1) Re-revaluated (2) Ion reactions

1998SIE/ARM(b)

(1) 1997KRE/FIE (2) 2003KRE/SCH

MoC(S)x–S2 xZ0 1

78.9G2.5 71.7G3

330.0G10.6 300.0G12.5

Ion reactions

2003KRE/SCH

MoC–CS

38.7G4.3

162G18

CID

2000ROD/ARM(b)

MoC–CS2

16.1G3

67.5G12.5

Ion reactions

2003KRE/SCH

Mo3 OC 7 –N2

O112

O469

ICR

2002GON/FIA(b)

MoC(O)x–NH xZ0 1 2

!92 !117 !71

!385 !490 !297

ICR

2002GON/FIA(b)

Mo3 OC 8 –NH

O44

O184

ICR

2002GON/FIA(b)

(continued)

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

750

Comprehensive Handbook of Chemical Bond Energies

Table 16.2.2 (continued) BDEs of MoC–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Mo3 OC 7 –2NH

O88

O368

ICR

2002GON/FIA(b)

Mo2 OC 5 –NH3 Mo3 OC 8 –NH3 Mo3O7(NH3)C –NH3

O56 O58 O58

O234 O243 O243

ICR

2002GON/FIA(b)

MoC–pyrrole

O69

O289

Kinetics

2000GAP/YAN

Mo2C(CO)x–CO xZ1 2

77.5G18.4 34.1G16.1

324G77 142.8G68

PI MS

1999QI/YAN

O3MoC(MoO3)x–MoO3 xZ0 1

112 86

469 360

Derived

2004GON(b)

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

751

16.2.3 MoK–X bonds Table 16.2.3 BDEs of MoL–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

MoK(O)x–O xZ3 4

O73 !50

O305 !209

GIB MS

1993KEE/CHE

MoK(O)x–O2 xZ4 5

13.8G1.2 35.0G4.6

58G5 146G19

CID

1992HOP/MCM

MoK(CO)5–(CO) MoK(CO)3(O)2–(CO)2

41.5G2.3 9.7G1.2

174G10 41G5

CID

1992HOP/MCM

MoK(CO)5–CHO

(1) %41.1 (2) %38

%172 %159

Review

(1) 1990SIM/BEA (2) 2004DAM

16.3 WK, WC–, and WK–X bonds 16.3.1 W–X bonds Table 16.3.1 BDEs of W–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W–W

(1) 116G23 (2) 159

486G96 666

(1) Correlation (2) Review

(1) 1986MOR (2) 1996SMI/YAT

W(100, surf.)–W

31.1G1.8 (phys)

130.3G7.7

FEM

1989STE/KUK

W(100, surf.)–W

184.5

772

FIM

1968PLU/RHO

(continued)

7366—CHAPTER 16—3/2/2007—10:53—CRCPAG—15372—XML MODEL B – pp. 713–780

752

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(110, surf.)–W

(1) 19.9 (phys) (2) 21.2G1.1 (3) 20.0 (4) 20.8 (5) 27.4G1.8

83.3 88.7G4.6 83.9 87.0 114.8G7.7

FIM

(1) 1970BAS/PAR (2) 1974AYR/EHR (3) 1975TSO/KEL (4) 1975COW/TSO (5) 1989STE/KUK

W(110, surf.)–W

(1) 189.1 (2) 184

791 770

(1) FIM (2) Review

(1) 1968PLU/RHO (2) 1995SEE/ALL

W(110, surf.)–W2

18.5G1.8 (phys)

77.2G7.7

FIM

1975COW/TSO

W(110, surf.)–W2

184

770

Review

1995SEE/ALL

W(111, surf.)–W

16 (phys)

66.9

FIM

1990CHO/KIM

W(111, surf.)–W

154.5

646.4

FIM

1968PLU/RHO

W(211, surf.)–W

(1) 13.0 (phys) (2) 19.7 (3) 19.0G0.7

54.4 82.4 79.5G2.9

FIM

(1) 1970BAS/PAR (2) 1980FLA/GRA (3) 1988WAN/EHR

W(211, surf.)–W

159

666

FIM

1968PLU/RHO

W(211, surf.)–W2

(1) 8.5G0.7 (phys) (2) 18.4G1.8

35.7G2.9

FIM

(1) 1974GRA/EHR(b)

77.2G7.7

159

666

W(211, surf.)–W2

(2) 1975COW/TSO

Review

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

1995SEE/ALL

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

753

W(211, surf.)–W3

8.5G0.7 (phys)

35.7G2.9

FIM

1974GRA/EHR(b)

W(321, surf.)–W

(1) 19.4 (phys) (2) 20.1G1.8 (3) 18.8–20.1

81.2 84.1G7.5 78–84

FIM

(1) 1970BAS/PAR (2) 1974AYR/EHR (3) 1989KAP-YAN

W(321, surf.)–W

170.6

714

FIM

1968PLU/RHO

Cl5W–WCl5

10.4

43.5

Derived from DfH0 in ref.

1996NIST

R(CO)3W–W(CO)3R RZh5-C5H5

81.0

339

Review

1994NOL

(WO3)–WO3

115G20

481G84

Review

1967DRO/GOL

W(110, surf.)–Mo

119.7

501

FIM

1977VED/GON

W(211, surf.)–Mo

(1) 12.8 (phys) (2) 13.1 (3) 16.4G0.5

53.6 54.8 68.5G1.9

FIM

(1) 1970BAS/PAR (2) 1975SAK/NAK (3) 1988WAN/EHR

W(211, surf.)–Mo

191

799

Review

1970BAR/PAR

W(211, surf.)–Mo2

6.0 (phys)

25

FIM

1975SAK/NAK

W(321, surf.)–Mo

12.7 (phys)

53

FIM

1975SAK/NAK

W(polycs. surf.)–Li

15 (phys)

63

FEM

1990GLA

W(polycs. surf.)–Li

64

268

FEM

1990GLA

(continued)

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

754

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(110, surf.)–Li

8.5 (phys)

36

CPD

1982LOB/NAU

W(110, surf.)–Li

64.1G2.1

268.2G8.7

TDS

1976HUR/OVE

W(111, surf.)–Li

11 (phys)

46

Review

1995SEE/ALL

W(111, surf.)–Li

62

259

Review

1995SEE/ALL

W(211, surf.)–Li

10 (phys)

42

Review

1995SEE/ALL

W(211, surf.)–Li

62

259

Review

1995SEE/ALL

W(polycs. surf.)–Na

13 (phys)

54

FEM

1990GLA

W(polycs. surf.)–Na

57

238

FEM

1990GLA

W(100, surf.)–Na

O53.5

O224

FEM

1968KLI/MED

W(110, surf.)–Na

6.2 (phys)

26

Review

1995SEE/ALL

W(110, surf.)–Na

(1) O59.3 (2) 58.8G0.9 (3) 63

O248 246.0G3.9 264

(1) FEM (2) TDS (3) Review

(1) 1968KLI/MED (2) 1976HUR/OVE (3) 1995SEE/ALL

W(111, surf.)–Na

O52.1

O218

FEM

1968KLI/MED

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

755

W(112, surf.)–Na

O53.0

O222

FEM

1968KLI/MED

W(polycs. surf.)–K

9.4 (phys)

39

FEM

1990GLA

W(polycs. surf.)–K

46

192

FEM

1990GLA

W(100, surf.)–K

9.9G0.9 (phys)

41.5G3.9

SIM

1984BAY/WAS

W(100, surf.)–K

57

238

SIM

1984BAY/WAS

W(110, surf.)–K

7.8 (phys)

32.8

FEM

1965SCH/GOM

W(110, surf.)–K

(1) 47.3G0.5 (2) 59

197.8G1.9 247

(1) TDS (2) Review

(1) 1976HUR/OVE (2) 1995SEE/ALL

W(211, surf.)–K

18 (phys)

75

Review

1995SEE/ALL

W(211, surf.)–K

59

247

Review

1995SEE/ALL

W(polycs. surf.)–Rb

10 (phys)

42

FEM

1990GLA

W(polycs. surf.)–Rb

41

172

FEM

1990GLA

W(polycs. surf.)–Cs

6.7 (phys)

28

FEM

1990GLA

W(polycs. surf.)–Cs

40

167

FEM

1990GLA

W(100, surf.)–Cs

64.6

270

FEM

1967GAV/VED

W(110, surf.)–Cs

13.1G0.5 (phys)

55.0G1.9

PE

1969LOV/WIE

(continued)

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

756

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(110, surf.)–Cs

(1) 73.8 (2) 70.6 (3) 71.5 (4) 73.0

308.7 295.2 299.1 305.4

TDS

(1) 1972KON/NAU (2) 1974TOD/RHO (3) 1980DES/PAP (4) 1986ALB

W(321, surf.)–Cs

17.5 (phys)

73

Review

1995SEE/ALL

W(polysc. surf.)–Be

86.2

360.8

TD

1961ZIN/ISH

W(110, surf.)–Be

19.1 (phys)

80

FEM

1960KOM/SAV

W(polysc. surf.)–Mg

65.3

273

TD

1961ZIN/ISH

W(polysc. surf.)–Ca

89.0

372

TD

1961ZIN/ISH

W(surf.)–Ca

76.1

318.4

Pulsed beam

1973MUL/WAS

W(polysc. surf.)–Sr

89.0

372

TD

1961ZIN/ISH

W(surf.)–Sr

(1) 97.1G5.1 (2) 85.3

406.2G21.2 357

TDS

(1) 1965MAD/PET (2) 1973MUL/WAS

W(polysc. surf.)–Ba

107.7

450.6

TD

1961ZIN/ISH

W(surf.)–Ba

94.5

395.6

Pulsed beam

1973MUL/WAS

W(100, surf.)–Ba

15 (phys)

63

Review

1995SEE/ALL

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

757

W(100, surf.)–Ba

(1) 103.5 (2) 115

433 481

(1) FIM (2) Review

(1) 1972BON/KON (2) 1995SEE/ALL

W(110, surf.)–Ba

21.2 (phys)

89

FEM

1973VLA/LOB

W(110, surf.)–Ba

96.6

404

FIM

1972BON/KON

W(111, surf.)–Ba

10.8 (phys)

45.2

Review

1995SEE/ALL

W(111, surf.)–Ba

115

481

Review

1995SEE/ALL

W(210, surf.)–Ba

10.6 (phys)

44.4

Review

1995SEE/ALL

W(211, surf.)–Ba

5.1–16.8 (phys)

21–70

Review

1995SEE/ALL

W(211, surf.)–Ba

(1) 103.5 (2) 115

433 481

(1) FIM (2) Review

(1) 1973MED/SME (2) 1995SEE/ALL

W(311, surf.)–Ba

19.1 (phys)

80

Review

1995SEE/ALL

W(100, surf.)–Sc W(110, surf.)–Sc W(111, surf.)–Sc

110.7 102.6 117.6

463.1 429.3 492.1

FIM

1974MAK/GUR

W(100, surf.)–Y W(110, surf.)–Y W(111, surf.)–Y

132.6 124.5 138.4

554.8 521.0 578.9

FIM

1974MAK/GUR

W(polycs. surf.)–La

154.5G4.6

646G19.3

TD

1973MED/ION

W(100, surf.)–La

138.1

578

FIM

1977GUP/MED

(continued)

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

758

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(110, surf.)–La

138.1

578

FIM

1977VED/GON

W(polycs. surf.)–Ce

7.4 (phys)

31

MS

1994GLA

W(polycs. surf.)–Ce

(1) 159 (2) 43

666 180

(1) TD (2) MS

(1) 1973MED/ION (2) 1994GLA

W(polycs. surf.)–Pr

145.3G4.6

608G19.3

TD

1973MED/ION

W(polycs. surf.)–Nd

147.6G4.6

617G19.3

TD

1973MED/ION

W(311, surf.)–Nd

15 (phys)

63

Review

1995SEE/ALL

W(311, surf.)–Nd

104

435

Review

1995SEE/ALL

W(polycs. surf.)–Sm

96.9G4.6

405G19.3

TD

1973MED/ION

W(polycs. surf.)–Eu

4.1 (phys)

17

MS

1988GLA

W(polycs. surf.)–Eu

(1) 69.2G6.9 (2) 43

289G29 180

(1) TD (2) MS

(1) 1973MED/ION (2) 1988GLA

W(polycs. surf.)–Gd

161.4G4.6

675G19.3

TD

1973MED/ION

W(polycs. surf.)–Tb

124.5G6.9

521G29

TD

1973MED/ION

W(polycs. surf.)–Ho

110.7G4.6

463G19.3

TD

1973MED/ION

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

759

W(polycs. surf.)–Er

119.9G4.6

502G19.3

TD

1973MED/ION

W(polycs. surf.)–Tm

101.5G6.9

425G29

TD

1973MED/ION

W(polycs. surf.)–Yb

64.6G6.9

270G29

TD

1973MED/ION

W(211, surf.)–Yb

16 (phys)

67

Review

1995SEE/ALL

W(211, surf.)–Yb

51

213

Review

1995SEE/ALL

W(polycs. surf.)–Lu

138.4G4.6

579G19.3

TD

1973MED/ION

W(311, surf.)–Th

58 (phys)

243

Review

1995SEE/ALL

W(311, surf.)–Th

178

745

Review

1995SEE/ALL

W(polysc. surf.)–Ti

79.8

334

MS

1976UST/FED

W(100, surf.)–Hf

12.2 (phys)

51

FEM

1994BEB/GUB

W(100, surf.)–Hf

140

586

Review

1995SEE/ALL

W(100, surf.)–V

29 (phys)

121

FIM

1994VLA/STA

W(100, surf.)–V

170

711

Review

1995SEE/ALL

W(110, surf.)–Ta

(1) 17.9 (phys) (2) 17.3

74.9 72.4

FIM

(1) 1970BAS/PAR (2) 1975TSO/KEL

W(110, surf.)–Ta

161

674

Review

1970BAS/PAR

(continued)

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

760

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(211, surf.)–Ta

11.2 (phys)

46.9

FIM

1970BAS/PAR

W(211, surf.)–Ta

140

586

Review

1970BAS/PAR

W(321, surf.)–Ta

15 (phys)

63

FIM

1978TSO/COW

W(321, surf.)–Ta

160

669

Review

1995SEE/ALL

W(polysc. surf.)–Cr

101

422

MS

1966SHE/CHO

W(100, surf.)–Cr

21 (phys)

88

FIM

1994VLA/STA

W(100, surf.)–Cr

198

828

Review

1995SEE/ALL

W(110, surf.)–Re

(1) 23.9 (phys) (2) 21–24

100 88–100

FIM

(1) 1970BAS/PAR (2) 1978TSO/COW

W(110, surf.)–Re

234

979

Review

1970BAS/PAR

W(211, surf.)–Re

(1) 20.3 (phys) (2) 19.8 (3) 19.1G0.5

84.9 82.8 80.0G1.9

FIM

(1) 1970BAS/PAR (2) 1976STO/GRA (3) 1988WAN/EHR

W(211, surf.)–Re

191

799

Review

1970BAS/PAR

W(211, surf.)–Re2

(1) 18.0G0.3 (phys) (2) 23.1G1.2

75.3G1.3

FIM

(1) 1976STO/GRA

96.5G4.8

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

(2) 1988WAN/EHR

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

761

W(321, surf.)–Re

20.4 (phys)

85.4

FIM

1970BAS/PAR

W(321, surf.)–Re

198

828

Review

1995SEE/ALL

W(110, surf.)–Rh

16.7G1.4 (phys)

70G6

FIM

1990DHA/BAS

W(110, surf.)–Rh

(1) 159 (2) 117.6

665 492

(1) Review (2) TDS

(1) 1995SEE/ALL (2) 1997KOL/BAU

W(110, surf.)–Rh2 W(110, surf.)–Rh3 W(110, surf.)–Rh4

16.1 (phys) 18.2 21.0

67.5 76.2 87.8

FIM

1990DHA/BAS

W(211, surf.)–Rh

12.5 (phys)

52.1

FIM

1988WAN/EHR

W(110, surf.)–Ir

(1) 18.0 (phys) (2) 22.4G0.5

75.3 93.6G1.9

FIM

(1) 1970BAR/PAR (2) 1989LOV/EHR

W(110, surf.)–Ir

(1) 138 (2) 156.8

577 655

(1) Review (2) TDS

(1) 1970BAS/PAR (2) 1997KOL/BAU

W(211, surf.)–Ir

(1) 13.4 (phys) (2) 12.1 (3) 15.5G0.5

56.1 50.6 64.6G1.9

FIM

(1) 1970BAR/PAR (2) 1975REE/EHR (3) 1988WAN/EHR

W(211, surf.)–Ir

94

393

Review

1970BAS/PAR

W(211, surf.)–Ir2

15.5 (phys)

65

FIM

1975REE/EHR

W(100, surf.)–Ni

(1) 34 (phys) (2) 23.3

142 97.4

FIM

(1) 1976ROU/PIQ (2) 1987KEL

W(100, surf.)–Ni

105.2

440

FIM

1976ROU/PIQ

(continued)

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

762

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(110, surf.)–Ni

(1) 11.3 (phys) (2) 11.3G0.5

47.3 47.3G1.9

FIM

(1) 1978BAS (2) 1987KEL(b)

W(110, surf.)–Ni

100–114

420–478

TDS

1986KOL/BAU

W(111, surf.)–Ni

20.2G2 (phys)

84.5G8

FIM

1978FLA/GRA

W(111, surf.)–Ni

105

439

Review

1995SEE/ALL

W(211, surf.)–Ni

10.6G0.5 (phys)

44.4G1.9

FIM

1995SEN/EHR

W(100, surf.)–Pd

32 (phys)

134

FIM

1978ROU/PIQ

W(100, surf.)–Pd

24 (phys)

100.4

FIM

1984ROU/PIQ

W(100, surf.)–Pd

103

431

Review

1995SEE/ALL

W(110, surf.)–Pd

(1) 18.4 (phys) (2) 11.8 (3) 24

77 49.2 100

FIM

(1) 1977JON/ROB (2) 1978BAS (3) 1984ROU/PIQ

W(110, surf.)–Pd

(1) w69 (2) 103 (3) 73.8

w289 431 309

(1) FIM (2) Review (3) TDS

(1) 1977JON/ROB (2) 1995SEE/ALL (3) 1997KOL/BAU

W(111, surf.)–Pd

17 (phys)

71

FIM

1978ROU/PIQ

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

763

W(211, surf.)–Pd

7.8 (phys)

32.8

FIM

1995SEN/EHR

W(211, surf.)–Pd

103

431

Review

1995SEE/ALL

W(110, surf.)–Pt

w14 (phys)

w59

FIM

1970BAR/PAR

W(110, surf.)–Pt

(1) 129 (2) 124.5

540 521

(1) Review (2) TDS

(1) 1970BAS/PAR (2) 1997KOL/BAU

W(110, surf.)–Pt2 W(110, surf.)–Pt3 W(110, surf.)–Pt4

15.5G1.4 (phys) 18.4G3.6 20.1G3.6

65G6 77G15 84G15

FIM

1976BAS

W(211, surf.)–Pt

55

230

Review

1970BAR/PAR

W(110, surf.)–Cu

(1) 74–89 (2) 84.6

309–371 354

(1) TDS (2) LEEM

(1) 1986KOL/BAU (2) 1996LUO/CAI

W(polysc.)–Ag

(1) 66.9 (2) 36.9G2.3

280 154.4G9.6

FIM

(1) 1969CHO/HEN (2) 1972JON

W(110, surf.)–Ag

(1) %11G1.2 (phys) (2) 5.8

%46.3G4.8

SEM

(1) 1983SPI/AKH

W(110, surf.)–Ag

(1) (2) (3) (4)

276 305 270–343 212.3G9.6

(1) MS (2) SEM (3) TDS (4) SEM

(1) 1973HUD/LO (2) 1983SPI/AKH (3) 1986KOL/BAU (4) 1990JON/MAR

W(100, surf.)–Au

11 (phys)

46

Review

1995SEE/ALL

W(100, surf.)–Au

80

335

Review

1995SEE/ALL

66 73 65–82 50.7G2.3

24.1

(2) 1990JON/MAR

(continued)

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

764

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(110, surf.)–Au

10 (phys)

42

Review

1995SEE/ALL

W(110, surf.)–Au

(1) 76–95 (2) 80

318–396 335

(1) TDS (2) Review

(1) 1986KOL/BAU (2) 1995SEE/ALL

W(211, surf.)–Au

8 (phys)

33

Review

1995SEE/ALL

W(111, surf.)–Cd

41–51

172–213

Mol. beam

1971WAG/VOO

W(crystal. surf.)–Hg

42.0G3.5

175.6G14.5

TDS

1968SWA/STR

W(100, surf.)–Hg

23.1 (phys)

96.5

TDS

1968SWA/STR

W(100, surf.)–Hg

44.3

185

TDS

1968SWA/STR

W(111, surf.)–Hg W(321, surf.)–Hg

11.8 (phys) 9.2

49.2 38.6

TDS

1968SWA/STR

W(100, surf.)–In

25.3 (phys)

106

SAM

1986MOR/BAR

W(100, surf.)–In

81

339

Review

1995SEE/ALL

(h5-C5H5)(CO)3W–GeMe3

64.8

271.1

Derived

1991CAR/KEP

(h5-C5H5)(CO)3W–SnMe3

75.6

316.5

Derived

1991CAR/KEP

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

765

W(100, surf.)–Pb

30.0 (phys)

125.4

FEM

1981MOR/DRE

W(100, surf.)–Pb

67

280

Review

1995SEE/ALL

W(111, surf.)–Pb

30.0 (phys)

125.4

FEM

1981MOR/DRE

W(111, surf.)–Pb

(1) 115 (2) 58

481 243

(1) TDS (2) Review

(1) 1975BER/FEL (2) 1995SEE/ALL

W(211, surf.)–Pb W(311, surf.)–Pb

85 85

356 356

TDS

1975BER/FEL

W(110, surf.)–He

0.08

0.34

HAS

1972WEI

W(110, surf.)–Ar

(1) (2) (3) (4)

7.5 8.0 11.5 12.3

FIM

(1) 1959GOM (2) 1964EHR (3) 1970ENG/GOM (4) 1979OXI/MOD

W(CO)5–Ar –Kr

%3 !6

%13 !25

Est. by exp.

1992WEL/WEI

W(CO)5–Xe

(1) 8.2G1.0 (2) 8.4G0.2

34.3G4.2 35.1G0.8

Transient IR

(1) 1992WEL/WEI (2) 1992WEI

W(110, surf.)–Xe

1.1G0.3 (phys)

4.6G1.3

FEM

1980CHE/GOM

W(110, surf.)–Xe

4.3

18

TDS

1981OPI/GOM

W(111, surf.)–Xe

9.3

38.9

Flash desorption

1974DRE/MAD

1.8 1.9 2.7 2.9

(continued)

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

766

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(CO)3(h5-C5H5)–H

(1) 72.3 (2) 81.0G1.1 (3) 72.4

302.5 338.9G4.6 303

(1) Electrochem. (2) Review (3) Review

(1) 1991PAR/HAN (2) 1994NOL (3) 2001TIL

W(CO)2(PMe3) (h5-C5H5)–H

(1) 69.6 (2) 69.6

291.2 291

(1) Electrochem. (2) Review

(1) 1991PAR/HAN (2) 2001TIL

(L)W(CO)3–H LZhydridotris(pyrazol)borate

65.7

275

Electrochem.

1993SKA/TIL

62.1

260

W(P(i-Pr)3)(CO)3(SPh)–H

53.2

222.6

Derived

1994LAN/JU(b)

W(H)(h5-C5H5)2–H

(1) 72.9G1 (2) 74.3G1.0

305G4 310.9G4.2

(1) Calorimetry (2) Review

(1) 1987CAL/DIA (2) 1994NOL

W(I)(h5-C5H5)2–H

65.2G3.3

273G14

Calorimetry

1987CAL/DIA

W(100, surf.)–H

w10.5G0.3 (phys)

w43.9G1.3 LOD

2002CAI/ALT

W(100, surf.)–H

(1) 64 (2) 67.6

268 283

(1) 1979TOY/SOM (2) 1988CHR

hydridotris (3,5-dimethylpyrazolyl)borate

Review

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

767

W(110, surf.)–H –D –T

4.09G0.10 (phys) 17.11G0.42 3.95G0.20 16.53G0.84 4.80G0.20 20.01G0.84

FEM

1985WAN/GOM

W(110, surf.)–H

68

285

Review

1988CHR

W(111, surf.)–H

70.3

294

Review

1988CHR

W(211, surf.)–H

69

289

Review

1991BEN

548G63 %544 R552 502 502 444 506

(1) Review (2) Derived

(1) 1974GUR/KAR (2) 1975HIL

W(F)x–F xZ0 1 2 3 4 5

(1) (2) (2) (2) (2) (2) (2)

F2SW–F

109

456

Derived

1975HIL

W(polycs. surf.)–F

(1) O69 (2) 103.8G3.5

O289 434G14

Ion beam

(1) 1976FLO/PRI (2) 1979BOL/BLA

(1) 101G10 (2) 100.1

423G42 419

(1) Review (2) Der. from DfH0 in ref.

(1) 1974GUR/KAR (2) 1996NIST

(2) 164.3 (2) 47.3 (2) 48.4

687 198 202

(1) 99 (2) 85.3G3.5

414 357G14

(1) Surf. Ioniz. (2) Ion beam

(1) 1977BIE/WAS (2) 1979BOL/BLA

W(Cl)x–Cl xZ0

1 4 5

W(polycs. surf.)–Cl

131G15 %130 R132 120 120 106 121

(continued)

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

768

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(100, surf.)–Cl

(1) 99 (2) 86.9G0.9 (3) 86

414 364G4 360

TDS

(1) 1979PRI/RAW (2) 1981KRA/BAU (3) 1988ZHO/YOO

W(110, surf.)–Cl

35

146

TDS

1980BON/ENG

W(111, surf.)–Cl

97

406

TDS

1980BON/ENG

W(Br)x–Br xZ0 5

(1) 78.7 (2) 37.2

329.3 155.6

(1) MS (2) Der. from DfH0 in ref.

(1) 1977KAP (2) 1996NIST

W(polycs. surf.)–Br

60G3.5

251G14

Ion beam

1979BOL/BLA

W(100, surf.)–Br

(1) 76 (2) 78

318 326

TDS

(1) 1980RAW/PRI (2) 1988ZHO/YOO

W(surf.)–I

w80

w335

TOF MS

1967MCC

W(100, surf.)–I

70

293

TDS

1988ZHO/YOO

(1) 160.6G10 (2) 161.4

672G42 675

(1) 1990SIM/BEA (2) 1996NIST

(3) 172G17 (2) 142.9 (2) 147.9

720G71 598 619

(1) Review (2) Der. from DfH0 in ref. (3) ICP-SIFT

W(O)x–O xZ0

1 2

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

(3) 2004BLA/KOY

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

769

Cl4W–O

116.3G9.3

486.7G39

Derived from DfH0 in ref.

1996NIST

W(polycs. surf.)–O

129.8

543

FEM

1972GOY/KIN

W(100, surf.)–O

(1) (2) (3) (4)

136 120–171 93.2 125–136

569 502–714 390 523–569

(1) TD (2) TD (3) Combined (4) Review

(1) 1968VAS/PTU (2) 1972BAC/DES (3) 1974WEL/KIN (4) 1991BEN

W(110, surf.)–O

(1) (2) (3) (4)

27G2 (phys) 14.5 24.1 24.1

113G8 61 101 100.8

(1) CPD (2) FEM (3) FEM (4) FEM

(1) 1977BUT/WAG (2) 1979CHE/GOM (3) 1980BOW/KIN (4) 1985TRI/GOM

W(110, surf.)–O

(1) (2) (3) (4)

138 126! 125–139 129

579 527! 523–582 540

(1) TD (2) FEM/TD (3) Review (4) Review

(1) 1968VAS/PTU (2) 1970KIH/GOM (3) 1991BEN (4) 1995SEE/ALL

W(111, surf.)–O

23.1 (phys)

96.7

TD

1967ZIN/ISH

W(211, surf.)–O

10–14 (phys)

42–59

FEM

1986TRI/GOM

W(320, surf.)–O

23.9

100

FEM

1980BOW/KIN

W(411, surf.)–O

52.6

220

FEM

1980BOW/KIN

(h5-C5Me5)2WaO

132

552

Derived

1998LUO/LAN

WSF2–S WF2–S WF3–S

105 126 115

439 527 481

Derived

1975HIL

(continued)

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770

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated atom or group)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(100, surf.)–S

%28.7 (phys)

%120

FIM

1980BEC/LEO

W(100, surf.)–S

113

473

Review

1995SEE/ALL

W(110, surf.)–S W(211, surf.)–S W(721, surf.)–S

15.1–20.1 17.9–19.1 24.9G1

63–84 75–80 104G4

FIM

1980BEC/LEO

W(100, surf.)–N

w35 (phys)

w146

FEM

1961EHR/HUD

W(100, surf.)–N

151–152

632–636

Review

1991BEN

W(110, surf.)–N

(1) w20 (phys) (2) 21

w84 88

(1) FEM (2) AES

(1) 1961EHR/HUD (2) 1977POL/EHR

W(110, surf.)–N

(1) 153 (2) 80

640 335

Review

(1) 1991BEN (2) 1995SEE/ALL

W(111, surf.)–N

w20 (phys)

w84

FEM

1961EHR/HUD

W(111, surf.)–N

151

632

Review

1991BEN

W–P

72.9G1

305G4

MS

1964GIN

W(110, surf.)–C

55

230

Review

1995SEE/ALL

7366—CHAPTER 16—3/2/2007—10:54—CRCPAG—15372—XML MODEL B – pp. 713–780

BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

771

W(110, surf.)–C

260

1088

Review

1995SEE/ALL

W(211, surf.)–C

53

222

Review

1995SEE/ALL

W(110, surf.)–Si

16.1G1.6

67.5G6.8

FIM

1981CAS/TSO

(CO)5W–H2

R16

R67

Est. by exp.

1994WEL/HOU

(1) 10.0G1.0 (2) 6.8G0.5 (2) 6.8G0.5

41.8G4.2 28.5G2.1 28.5G2.1

Calorimetry

(1) 1991ZHA/GON (2) 1997BEN/KUB

W(polycr. surf.)–H2

(1) (2) (3) (4)

31 (phys) 36 35 32

130 151 146 134

(1) TD (2) TD (3) FDMS (4) TD

(1) 1960HIC (2) 1964PTU/CHU (3) 1966MIM/HAN (4) 1974KO/SCH

W(polycr. surf.)–H2

(1) (2) (3) (4)

51.9 46.4 62.9 45.9

217 194 263 192

Calorimetry

(1) 1953WAH/KEM (2) 1964BRE/HAY (3) 1969ELE/NOR (4) 1977COU/JOH

W(100, surf.)–H2

(1) (2) (3) (4)

32.3G1.0 32.5 40 38

135.1G4.2 156 167 159

(1) FDMS (2) Review (3) TDS (4) Mol. beam

(1) 1971TAM/SCH(b) (2) 1978MAD/BEN (3) 1984SMI/BAR (4) 1989ALN/CAS

W(100, surf.)–D2

32.6

136.4

FDMS

1971TAM/SCH(b)

W(110, surf.)–H2

(1) 32.7G1.0 (2) 33

136.8G4.2 138

(1) FDMS (2) Review

(1) 1971TAM/SCH(b) (2) 1978MAD/BEN

W(110, surf.)–HD

0.41 (phys)

1.72

Scattering

1985RET/DEL

(P(C6H11)3)(CO)3W –(h2-H2) –(h2-D2)

(continued)

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772

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(111, surf.)–H2

(1) 36.6G1.5 (2) 31

153G6.3 130

(1) FDMS (2) Review

(1) 1971TAM/SCH(b) (2) 1978MAD/BEN

W(211, surf.)–H2

16 (b1-state) 35 (b2-state)

67 146

TDS

1973RYE/BAR

W(surf.)–I2

w40

w167

TOF MS

1967MCC

W(polycr. surf.)–O2

(1) 194 (2) 122 (3) w138.4 (4) 145.3 (5) 136

811 510 w579 608 570

(1) Calorimetry (2) Calorimetry (3) TD (4) TD (5) Review

(1) 1960BRE/HAY (2) 1966BRE/GRA (3) 1967PTU/CHU (4) 1972WAS/WER (5) 1982RAO/KAM

(P(C6H11)3)2(CO)3W–N2

13.5G1.0

56.5G4.2

Calorimetry

1991ZHA/GON

W(polycr. surf.)–N2

(1) 9–20 (phys) (2) 14–24

38–84 59–100

TD

(1) 1961EHR(b) (2) 1967HAY/KIN

W(polycr. surf.)–N2

(1) 95 (2) 92 (3) 103.7 (4) 95 (4) 90.8

397 385 434 397 380

Calorimetry

(1) 1950BEE (2) 1959KIS (3) 1971YAM/OGU (4) 1974GLA/SOM (4) 1977COU/JOH(b)

W(100, surf.)–N2

(1) 9 (2) 9.2 (phys) (2) 10.5

38 38.5 43.9

TD

(1) 1965DEL/EHR (2) 1971HAN/SCH

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BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

773

W(100, surf.)–N2

(1) 75 (2) 80

314 335

TD

(1) 1965DEL/EHR (2) 1971HAN/SCH

W(110, surf.)–N2

(1) !9 (phys) (2) 10.3

!38 43

(1) TD (2) LEED

(1) 1965DEL/EHR (2) 1990LIN/SHA

W(110, surf.)–N2

79

331

Kinetics

1971TAM/SCH

W(111, surf.)–N2

9–16 (phys)

38–67

TD

1965DEL/EHR

W(111, surf.)–N2

w75

w314

TD

1965DEL/EHR

W(W)x–N2 xZ4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25

16 16 17 17 16 17 15 18 18 18 25 16 25 25 24 24 24 26 26 25 25 26

67 67 71 71 67 71 63 75 75 75 105 67 105 105 100 100 100 109 109 105 105 109

FTR

1996MIT/RAY

(h5-C5Me5)(CO)3W–SH

63

264

Derived

1999BAU/CAP

(continued)

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774

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds

The broken bonds (boldfaceZdissociated atom or group) W(CO)x–CO xZ3

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 25G15 (2) O33 (2) 36–39 (3) 40.4G15 (3) 38G5 (4) 46.0G2

105G63 O138 151–163 169G63 159G21 192.5G8.4

W(polycr. surf.)–CO

(1) 20 (phys) (2) 16 (3) 23 (4) 13 (5) 18.7

W(polycr. surf.)–CO

Methods (reference in parentheses)

References

(1) Mol. beam (2) LP

(1) 1990VEN/HOU (2) 1991RAY/ISH

(3) PAC

(3) 1983BER/SIM

(4) LP

(4) 1984LEW/GOL

84 67 96 54 78

(1) FEM (2) FEM (3) TD (4) TD (5) TD

(1) 1962ROO/REI (2) 1963SWA/GOM (3) 1964RIG (4) 1965UST/AGE (5) 1967DEG

(1) 76 (2) 77 (3) 89 (4) 77.1 (5) 74.5

318 322 372 323 318

(1) FEM (2) TD (3) TD (4) TD (5) TD

(1) 1963SWA/GOM (2) 1964RIG (3) 1965UST/AGE (4) 1967DEG (5) 1972WIN

W(100, surf.)–CO

(1) 21G2 (phys) (2) 27G4

88G8 113G17

TDS

(1) 1972CLA/SCH (2) 1973VIS/SCH

W(100, surf.)–CO

57G4 64G4 82G4

238G17 268G17 343G17

TDS

1973VIS/SCH

W(110, surf.)–CO

(1) 23.1 (phys) (2) 21G2 (3) 10–25 (4) 22.3 (5) 20.6

97 88G8 42–105 93 86

(1) TDS (2) FDMS (3) TDS (4) FEM (5) XPS

(1) 1968AGE/PTU (2) 1972CLA/SCH (3) 1973KOH/GOM (4) 1979CHE/GOM (5) 1983UMB/MEN

W(110, surf.)–CO

(1) 80.7 (2) 69.5G3

338 291G13

(1) TDS (2) TDS

(1) 1968AGE/PTU (2) 1971KOH/GOM

4 5

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BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

775

(3) 93G5 (4) 78

389G17 326

(3) FDMS (4) Review

(3) 1972CLA/SCH (4) 1995SEE/ALL

W(111, surf.)–CO

27 (phys)

113

Review

1974ERT

W(311, surf.)–CO

27.7 (phys)

116

TDS

1968AGE/PTU

W(311, surf.)–CO

87.6

367

TDS

1968AGE/PTU

W(CO)5–CS

71.9G8

301G33

MS

1980MIC/FLE

W(110, surf.)–WSi

13.6G0.5 (phys)

56.9G1.9

FIM

1985WRI/EHR

W(110, surf.)–WSi

155

649

Review

1995SEE/ALL

W(polycr. surf.)–CO2

(1) 109

456

(1) Review

(1) 1964HAY/TRA

(2) 122

510

(2) Calorimetry

(2) 1965BRE/HAY

W(CO)5–N2O

(1) 22G2 (2) 14.1G0.5

92G8 59.0G2.1

(1) IR (2) FT-IR

(1) 1991GOG/WEL (2) 1993WEI/WEL

W(polycr. surf.)–NH3

(1) 62 (2) 72

259 301

(1) Calorimetry (2) Review

(1) 1953WAH/KEM (2) 1964HAY/TRA

W(CH3)5–CH3

38.2G1.5

159.8G6.3

Review

1994NOL

W(CH3)(h5-C5H5)2–CH3

(1) 47.1G0.4 (2) 52.8G0.9

197G3 220.9G4

(1) Calorimetry (2) Review

(1) 1987CAL/DIA (2) 1994NOL

W(polycr. surf.)–C2H4

100.8

422

Calorimetry

1950BEE/COL

(continued)

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776

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.1 (continued) BDEs of W–X Bonds

The broken bonds (boldfaceZdissociated atom or group)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W(CO)5–CF2Cl2

19.6G0.6

82.0G2.5

IR

1991BOG/WEL

W(Pr3)(CO)3(H)–SC6H5

40.4G3

169G13

Derived

1997LAN/JU

W(CO)5–C(OCH3)(C6H5)

(1) 85.1G3.8 (2) 85.8G4.3

356G16 359G18

(1) Calorimetry (2) Review

(1) 1984ALT/CON (2) 1990SIM/BEA

W(CO)5–P(C6H5)3

(1) 75.3G3.1 (2) 76.2G3.8

315G13 319G16

(1) Calorimetry (2) Review

(1) 1984ALT/CON (2) 1994DIA/PIE

64.6G2.3

270.3G9.6

MS

1971LAP/CAR

75.6G3.5

316.3G14.6

W(CO)5 –CH4 –C2H6 –C3H8 –n-C4H10 –i-C4H10 –n-C5H12 –n-C6H14 –c-C3H6 –c-C5H10 –c-C6H12

!5 7.4G2 8.1G2 9.1G3 8.6G2 10.6G3 10.8G3 8.8G2 10.2G3 11.6G3

!21 31.0G8.4 33.9G8.4 38.1G12.6 36.0G8.4 44.4G12.6 45.2G12.6 36.8G8.4 42.7G12.6 48.5G12.6

TR-IR

1990BRO/ISH

W(CO)5–CH3F –CH3F2 –CHF3 –CF4 –C2H5F

11.2G3 O5 !5 !5 12.2G3

46.9G12.6 O21 !21 O21 51.0G12.6

TR-IR

1990BRO/ISH

(h5-C5H5)(CO)3 Mn–GeMe3 (h5-C5H5)(CO)3 Mn–SnMe3

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BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

W(CO)5–pyridine

163 165.3 148.5 138.1 182 187.0 178.7

(1) Calorimetry (2) Derived

(1) 1984ALT/CON (2) 1984LEW/GOL

(1) 13.4G2.8 (2) 14.7 (2) 29.4

56.1G11.7 61.5 123.0

PAC

(1) 1989MOR/PAR (2) 1992BUR

18.9G0.4 26.5G1.5

79.1G1.7 110.9G6.3

Calorimetry

1991ZHA/GON

(h5-C5H5)(CO)3 W–CH(CH3)C6H5

29

121

Thermolysis

1992MAN/HAL

fac-(h2-phen)(CO)3 W–C60 phenZ1, 10-phenanthroline

25.1

105

Kinetics

2004RIV/CRE

–pyrazine –pyrazole –piperidine –NCCH3

W(CO)5–nC7H16 –HSiEt3

(P(C6H11)3)2(CO)3W–L LZpyridine P(OMe3)3

(1) (2) (2) (2) (1) (2) (2)

39 39.5 35.5 33.0 43.5 44.7 42.7

777

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778

Comprehensive Handbook of Chemical Bond Energies

16.3.2 WC–X bonds Table 16.3.2 BDEs of WD–X Bonds

The broken bonds (boldfaceZdissociated fragment) C

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

W –H

(1) 38.2 (2) 53.2G1.2

160 222.5G5

GIB MS

(1) 2001ARM/ZHA (2) 2002ZHA/RUE

CHWC–H

(1) 57.7G2.3 (2) 71.0G6.7

241.4G9.6 297G28

(1) PD (2) CID

(1) 2001SIM/LEM (2) 2006ARM/SHI

(CO)6WC–H

(1) 64G3 (2) 61.4G2.2

267.8G12.6 (1) Thermochem. 257G9 (2) Review

(1) 1981STE/BEA (2) 1990SIM/BEA

H–WCH(CO)2(PMe3) (h5-C5H5)

O75.5

O316

Electrochem.

1992TIL(b)

59.5 60.6 61.0 62.0 64.7 68.0

248.9 253.6 255.2 259.4 270.7 284.5

Electrochem.

1996WAN/ANG

60.4

252.7

64.5

269.9

Electrochem.

1993SKA/TIL

(L)(CO)2WC–H LZ(CO)(PMePh2)3 (CO)(PEtPh2)3 (CO)(PEt2Ph)3 (CO)(PMe3)3 (CO)(PEt3)3 (dppm)2 dppm: Ph2P(CH2)PPh2 (CO)(tripod) tripod: MeC(CH2PPh2)3 (CO)(triphos) triphos: PhP(CH2CH2PPh2)2

(CO)3(L)-WC–H LZhydridotris 57.8 (pyrazol)borate hydridotris(3,5-dimethyl- 55.2 pyrazolyl)borate

242 231

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BDEs of Cr(CrG)–, Mo(MoG)–, and W(WG)–X Bonds

779

WC–F

106G23

444G96

Der. from IP in ref.

1996NIST

WC–C

(1) 90.6G11.5 (2) 115.3G5.1

379G48 483G21

(1) UV PI (2) GIB MS

(1) 1997QI/YAN(c) (2) 2006ARM/SHI

WC(CO)–C

89.2G13.8

373G58

UV PI

1997QI/YAN(c)

WC–CH

(1) 142.2G7.2 (1) 138.6G6.5 (1) 109.5G1.4 (2) 109.1G1.4 (3) O111 (1) 39.7G6.5 (2) w53.3G2.3 (4) 37.3

595G30 580G27 458G6 456.4G5.8 O464 166G27 w222.9G9.6 156

(1) CID (2) CID

(1) 2003ARM (2) 2006ARM/SHI

(3) FT-ICR

(3) 1991IRI/BEA

(4) CID

(4) 2001ARM/ZHA

WC–C2H2

76.1G9.2

318G39

FT-ICR

1998GEE/BOI

WC–C2H4

25

104.6

Review

1998SCH/SCH

(1) 126G10 (2) 166G10 (1) 132 (3) O119

527G42 695G42 552 O498

(1) Derived (2) ICP-SIFT

(1) 2000SCH/SCH (2) 2004BLA/KOY

(3) Derived

(3) 2004LAV/BLA

(1) 61.1 (2) 79.8G3.5 (3) !10.4 (1) 47.7 (2) 92.9G2.3 (3) %55.6G3.7 (1) 51.4 (2) 23.8G2.3 (3) 54.4G3.0 (1) 42.4 (2) 30.2G2.3 (3) 42.7G3.0 (1) 44.3 (2) 49.1G1.2 (3) 38.7G3.2

255.7 333.9G14.5 !43.4 199.7 388.7G9.6 %232.5G15.4 215.2 99.4G9.6 227.7G12.5 177.5G9.6 126.4G9.6 178.5G12.5 185.2 205.5G4.8 162.1G13.5

(1) MS (2) PI (3) PIE

(1) 1980MIC/FLE (2) 1997QI/YAN(c) (3) 1997CHE/LIA

–CH2 –CH3

WC(O)x–O xZ0 1

WC(CO)x–CO xZ0 1 2 3 4

(continued)

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780

Comprehensive Handbook of Chemical Bond Energies

Table 16.3.2 (continued) BDEs of WC–X Bonds

The broken bonds (boldfaceZdissociated fragment) 5

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 39.2 (2) 41.5G0.7 (3) 36.0G2.1

164.0 173.7G2.9 150.5G8.7

W2C(CO)x–CO xZ1 2 3 4 5

101.0G23 79.8G18 51.2G15 38.0G13 54.0G10.4

423G96 334G77 214G63 159G53 226G43

UV PI

1997QI/YAN(c)

WC–pyrrole

O50

O209

Kinetics

2000GAP/YAN

16.3.3 WK–X bonds Table 16.3.3 BDEs of WL–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

WK(O)5–O2

40.8G3.5

171G15

CID

1992HOP/MCM

(L)WK–CO LZ(CO)3(O) (CO)5 (CO3)(O)2

1.66G0.1 38.0G2.3 %2.3

7.0G0.4 159G10 %9.6

CID

1992HOP/MCM

(1) %46.4 (2) %43

%194 %180

Review

(1) 1990SIM/BEA (2) 2004DAM

WK(CO)5–CHO

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chapter seventeen

BDEs of Mn(Mn G )–, Tc(Tc C ), and Re(ReG)–X bonds 17.1 Mn–, MnC–, and MnK–X bonds 17.1.1 Mn–X bonds Table 17.1.1 BDEs of Mn–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Mn–Mn

(1) 7.5–12.9 (2) 11.0 (3) 11.0 (4) %19.3 (5) 14.7G2.3

31–54 46 46.2 %80.8 61.6G9.6

(1) MS (2) Review (3) Raman (4) Review (5) PD

(1) 1968KAN/LIN (2) 1979MIE/GIN (3) 1984MOS/DIL (4) 1986MOR (5) 2002TER/MIN

F3Mn–MnF3

50.4G0.6

210.9G2.5

MS

2002CIC/RAU

(CO)5Mn–Mn(CO)5

(1) 22.5 (2) 41 (3) 38G5 (4) O42 (5) 44.2G2

94 171 159G21 O176 185G8

(1) Calorimetry (2) PES (3) PAC (4) Photolysis (5) Review

(1) 1982CON/ZAF (2) 1985SIM/SCH (3) 1986GOO/PET (4) 1988SMI (5) 1990SIM/BEA

(CO)5Mn–Re(CO)5

35.6G2.6

149G11

Derived

1992CON

Mn–Co

12.0G1.9

50G8

CID

1991HOP/MCM(b)

(continued)

781

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Comprehensive Handbook of Chemical Bond Energies

Table 17.1.1 (continued) BDEs of Mn–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(CO)5Mn–Co(CO)4

22.9G2.9

96G12

Derived

1992CON

Mn–Ag

23.7G5

99.2G21

Review

1986MOR

Mn–Au

(1) 43.4G3.0 (2) 47.3G5

181.6G12.6 197.7G21

(1) MS (2) Review

(1) 1968MO/DRO (2) 1986MOR

Mn–H

(1) 39.9G1.5 (2) 60.9G1.2

167G6 255G5

(1) Review (2) Spectroscopy

(1) 1996ARM/KIC (2) 1997NAG/RAJ

Mn–D

75.5G1.4

316G6

Spectroscopy

1997NAG/RAJ

(CO)5Mn–H

(1) 50.9 (2) 63 (3) O70 (4) 58.6G2.4 (5) 68.0

213G10 264 O293 245G10 284.5

(1) Calorimetry (2) Kinetics (3) LP (4) Review (5) Electrochemical

(1) 1982CON/ZAF (2) 1986BIL/GRI (3) 1988SMI (4) 1990SIM/BEA (5) 1991PAR/HAN

(R)Mn(CO)4–H RZPPh3 PEtPh2

(1) 68.4 (2) 71

286.2 297.1

Electrochemical

(1) 1991PAR/HAN (2) 1991EIS/LAW

p-InP(solid)Mn–H

31.1G2.3

130.3G9.6

Kinetics

1992PEA/HOB

Mn(polycs. surf.)–H

w12

w50

TD

1971ROB/BIC

Mn–F

(1) 101.2G3.5 (2) 104.5G2.3 (3) 106.4G1.8

423.4G14.6 437.2G9.6 445.2G7.5

(1) MS (2) CL (3) HT MS

(1) 1964KEN/EHL (2) 1996DEV/GOL (3) 2002BAL/CAM

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BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X Bonds

783

Mn–Cl

80.9G1.6

338.5G6.7

MS

1995HIL

Mn–Br –I

75.1G2.3 67.6G2.3

314.2G9.6 282.8G9.6

Spectroscopy

1968GAY

(CO)5Mn–Cl

(1) 70.3G2.4 (2) O90 (1) 57.8G1.4 (2) O77

294G10 O377 242G6 O322

(1) Calorimetry (2) LP

(1) 1982CON/ZAF (2) 1988SMI

(CO)5Mn–I

(1) 46.6G1.4 (2) O66 (3) 54.0

195G6 O276 225.9

(1) Calorimetry (2) LP (3) Review

(1) 1982CON/ZAF (2) 1988SMI (3) 1992DRA/WON

Mn–O

(1) 89.0G1.8 (2) 83.7G6 (3) 88.3G1.8 (4) 86.5G6 (5) 96.3G10

372.4G7.7 350G25 369.5G7.7 362G25 403G42

(1) MS (2) GIB MS (3) Spectrometry (4) GIB MS (5) Review

(1) 1984SMO/DRO(b) (2) 1986ELK/ARM (3) 1989MER (4) 1990SUM/ARM (5) 1990SIM/BEA

Mn(O)–O

115

481

Derived

1994HIL/LAU(b)

Mn–S

72G4

301G17

MS

1965WIE/GIL

Mn–Se

57.2G2.2

239.3G9.2

MS

1978SMO/PAT

Mn(polycr. surf.)–H2

0.9 (phys)

3.8

Review

1964HAY/TRA

Mn(polycr. surf.)–H2

17

71

Review

1964HAY/TRA

Mn(polycr. surf.)–O2

(1) 151.8 (2) 150

635 628

(1) Calorimetry (2) Review

(1) 1960BRE/HAY (2) 1965BRE/HAY

–Br

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 17.1.1 (continued) BDEs of Mn–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(3) 184

770

(3) Review

(3) 1982RAO/KAM

MnO(polycr. surf.)–O2

24

100

Review

1964HAY/TRA

Mn(OH)x–OH xZ0 1

77 105

322 439

Derived

1994HIL/LAU(b)

(MnO)–H

83.5G10

349.4G42

Derived

This volume

(MnO)–OH

89

372

Derived

1994HIL/LAU(b)

MnO(polycs. surf.)–CO

64.4

269

Review

1964HAY/TRA

MnBr(CO)4–CO Mn2(CO)9–CO

44 38

184 159

LP

1988SMI

(h5-C5H5)(CO)2 Mn–CO

(1) 55 (2) 46.7G1.7 (3) 46.8G2.1

230 195.4G7.1 195.8G9.2

Review

(1) 1990BUR (2) 1990KLA/SEL (3) 1992HES/SUN

Mn(polycr. surf.)–CO

78

326

Calorimetry

1965BRE/HAY

Mn(polycr. surf.)–CO2

(1) 53 (2) 63

222 264

(1) Review (2) Calorimetry

(1) 1964HAY/TRA (2) 1965BRE/HAY

Mn(CO)5–CH2F –CHF2

33.2G2.6 34.4G2.6

139G11 144G11

PIMS

1990SIM/BEA

Mn(CO)5–CF3

(1) 41.1G1.7 (2) O61

172G7 O255

(1) Calorimetry (2) LP

(1) 1982CON/ZAF (2) 1988SMI

7366—CHAPTER 17—6/2/2007—13:12—JEBA—15373—XML MODEL B – pp. 781–801

BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X Bonds

785

(3) 48.5G1.4

203G6

(3) Review

(3) 1990SIM/BEA

Mn–CH3

(1) 12.7G3.9 (2) O8.3G2.8 (3) 27.9G2.1

53G16 O35G12 116.7G8.7

(1) GIB MS (2) Review (3) Derived

(1) 1990SUN/ARM (2) 1996ARM/KIC (3) 1996PAR/NIE

Mn(CO)5–CH3

(1) 36.6G1.2 (2) O56 (3) 44 (4) 45.9G2.6 (5) 44.7G0.9

153G5 O234 184 192G11 187.0G3.8

(1) Calorimetry (2) LP (3) Review (4) Review (5) Review

(1) 1982CON/ZAF (2) 1988SMI (3) 1988STO/BER (4) 1990SIM/BEA (5) 1994NOL

Mn(CO)5–C(O)CH3

(1) 30.8G2.9 (2) O50 (3) 39 (4) 38.2G2.4 (5) 39

129G12 O209 163.2 160G10 163.2

(1) Calorimetry (2) LP (3) Review (4) Review (5) Review

(1) 1982CON/ZAF (2) 1988SMI (3) 1988STO/BER (4) 1990SIM/BEA (5) 1994NOL

Mn(CO)5–C(O)CF3

(1) 35.1G2.6 (2) O55 (3) 42.1G3.3

147G11 O230 176G14

(1) Calorimetry (2) LP (3) Review

(1) 1982CON/ZAF (2) 1988SMI (3) 1990SIM/BEA

Mn(CO)5–C(O)C2H5 –C(O)C3H7

43.3 41.8

181 175

Review

1990SIM/BEA

Mn(CO)5–(h1-C3H5) –(h3-C3H5)

31.1G2.6 48.5G2.4

130G11 203G10

Derived

1992CON

Mn(h5-C5H5)x– (h5-C5H5) xZ0 1

69.2 48.9

289.4 204.5

EI

2001OPI

Mn(CO)5–C6H5

(1) 40.6G2.6 (2) O60 (3) 49 (4) 49.5G2.6

170G11 O251 205 207G11

(1) Calorimetry (2) LP (3) Review (4) Review

(1) 1982CON/ZAF (2) 1988SMI (3) 1988STO/BER (4) 1990SIM/BEA

Mn(CO)5–C(O)C6H5

(1) 21.3G2.4 (2) O41

89G10 O172

(1) Calorimetry (2) LP

(1) 1982CON/ZAF (2) 1988SMI

(continued)

7366—CHAPTER 17—6/2/2007—13:12—JEBA—15373—XML MODEL B – pp. 781–801

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Table 17.1.1 (continued) BDEs of Mn–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(3) 30.4G2.6

127G12

(3) Review

(3) 1990SIM/BEA

Mn(CO)5–CH2C6H5

(1) 20.8G2.9 (2) 32G5 (3) O40 (4) 29 (5) 30.8G2.4

87G12 134G21 O167 121 129G10

(1) Calorimetry (2) PES (3) LP (4) Review (5) Review

(1) 1982CON/ZAF (2) 1985SIM/SCH (3) 1988SMI (4) 1988STO/BER (5) 1990SIM/BEA

Mn(CO)4(PL3)–L LZCH2-p-MeO–C6H4

%25

%105

Kinetics

1982NAP/SAN

(h5-C5H5)-Mn(CO)2–L LZCH2Cl2 CH2Br2 n-BuCl n-BuBr n-C5H11Br

17 20 19.5 21 21

71 84 82 88 88

Derived

1992YAN/YAN

(h5-C5H5)-Mn(CO)2–L LZCH3C(O)CH3 cis-cyclooctene S(C4H9)2

17.4G1.0 24.5G2.3 28.7G2.2

72.8G4.2 102.5G9.6 120.1G9.2

Derived

1990KLA/SEL

(1) 10

42

Derived

(1) 1992BUR

(2) 8G1 (1) 24

34G4 100

(h5-C5H5)-Mn(CO)2 –THF THFZtetrahydrofuran

(1) 16.1G1.4 (2) 24G2 (3) 23.3G2.0 (3) 24.7G2.0

67.4G5.9 100.4G8.4 97.5G8.4 103.3G8.4

Derived

(1) 1990KLA/SEL (2) 1992YAN/YAN (3) 1999COL/DUL

(h5-C5H5)-Mn(CO)2– PhMe

14.2G0.8

59.4G3.3

Low Tem IR

2000BEN

(h5-C5H5)-Mn(CO)2 –nC7H16 –HSiEt3

(2) 1992HES/SUN

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BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X Bonds

787

(CO)5Mn–SiMe3 –GeMe3

60.9 55.3

254.7 231.6

MS

1973BUR/STO

(CO)5Mn–SnMe3

(1) 57.9 (2) 47.0 (2) 48.2 (3) 61G8 (2) 51.7

242.2 196.8 201.6 255G33 216.1

MS

(1) 1973BUR/STO (2) 1978SPA

47.0 51.7 48.2

196.8 216.1 201.6

MS

–SnPh3 –SnMe2Cl

(CO)5Mn–Sn(CH3)3 –Sn(CH3)2Cl –Sn(C6H5)3

(3) 1974CLA/RAK

1978SPA

17.1.2 MnC–X bonds Table 17.1.2 BDEs of MnD–X Bonds

The broken bonds (boldfaceZdissociated fragment) MnC–Mn

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(1) 32.9 (2) 48.4G6.9 (3) 30.9

137.6 202.6G29 129

(1) PD (2) ICR (3) Review

(1) 1985JAR/ILL (2) 1989HOU/VUL (3) 1996SMI/YAT

MnCMnx–Mn xZ1 2 3 4 5

(1) 19.1G1.2 (1) 24.0G1.6 (2) 39.2G1.8 (2) 24.0G2.3 (2) 33.7G2.5

80.1G4.8 100.3G6.8 164.0G7.7 100.3G9.6 140.9G10.6

PD

(1) 2002TER/MIN (2) 2005TON/TER

MnCMn–Mn2

13.8

57.9

PD

2002TER/MIN

(CO)5MnC–Mn(CO)5

(1) 39.7 (2) R48.4

166 R202.6

(1) Review (2) CID

(1) 1990SIM/BEA (2) 1991YU/LIA

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 17.1.2 (continued) BDEs of MnC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(CO)4MnC–Mn(CO)5

R48.4

R202.5

CID

1991YU/LIA

MnC–H

(1) 48.5G3.4 (2) 48.4G1.4

203G14 202.5G5.9

(1) GIB MS (2) Review

(1) 1986ELK/ARM(b) (2) 1987SCH/GOD

(1) 53G5 (2) 41.1G2.4 (1) 87G3 (2) 83.4G2.6

222G21 172G10 364.0G12.6 349G11

(1) Thermochemical (2) Review

(1) 1981STE/BEA(b) (2) 1990SIM/BEA

(1) 67G3 (2) 63.8G2.6 (1) 71G3 (2) 67.6G3.1

280.3G12.6 267G11 297.1G12.6 283G13

(1) Thermochemical (2) Review

(1) 1981STE/BEA(b) (2) 1990SIM/BEA

MnC 2 ðCOÞ10 –H

48.8G3.1

204G13

Review

1990SIM/BEA

MnC–F

76.6G5.7

321G24

Derived from IP in ref.

1996NIST

MnC–Cl –I

O50.5 O50.5

O211 O211

Ion reactions

1989STR/RID

MnC(H2)–H2 xZ0 1 2 3

1.9G0.4, at 0 K 1.7G0.4 w1.4 w1.2

7.9G1.7 7.1G1.7 w5.9 w5

Equilibrium

1997WEI/KEM

HMnC(H2)x–H2 xZ0 1

7.2G0.5, 0K 4.8G0.5

30.1G2.1 20.1G2.1

Equilibrium

1997WEI/KEM

(CO)5MnC(H)x–H xZ0 1

(L)(CO)3MnC–H LZ(CH3)(CO)2 (CH3C5H4)

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BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X Bonds

789

MnC–CH2 –CH3

70.6G3 51.4G2.3

295G13 215G10

GIB MS

1990SUN/ARM

MnC(CO)5–CH3

32.7G1.4 31.5G3.6

137G6 132G15

Review

1990SIM/BEA

MnC(CO)5–CH2F –CHF2 –CF3

19.6G1.4 13.9G1.4 17.2G1.4 22.2G3.6

82G6 58G6 72G6 93G15

Review

1990SIM/BEA

MnC(CO)5–CH4

O7.2

O30

ICR

1991HOP/MCM

(1) 21.7G2.9 (2) 20 (1) 21.0G3.5

91G12 84 88G14

(1) Ion reactions (2) Review

(1) 1998SIE/JAR (2) 1998SCH/SCH

(1) 74.0 (2) 77.9G2.3 (1) 49.3 (2) 79.1G2.3

309.7 326.1G9.6 206.5 330.9G9.6

(1) EI (2) PES

(1) 2001OPI (2) 2002LI/SZT

(1) 31.8G2.2 (2) 34.6G2.3 (1) 48.5G3.8

133G9 145G10 203G16

(1) GIB MS (2) FT ICR

(1) 1995MEY/KHA (2) 1997LIN/CHE(b)

MnC(CO)5–C6H6

32G5

134G21

Thermochemical

1985SIM/SCH

MnC(CO)5–C6H5CH3

36.6G4.1

153G17

Review

1990SIM/BEA

MnC–O

(1) 58.3G13.8 (1) 57.2G2.3 (2) 68.1G3

244G58 239G10 285G13

(1) Thermochemical (1) CID (2) GIB MS

(1) 1982ARM/HAL

MnC(C2H4)x–C2H4 xZ0 1

MnC(h5-C5H5)x–(h5C5H5) xZ0 1

MnC(C6H6)x–C6H6 xZ0 1

(2) 1990FIS/ELK

(continued)

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790

Comprehensive Handbook of Chemical Bond Energies

Table 17.1.2 (continued) BDEs of MnC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) MnC–OH

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(1) 82.0 (2) 81G4 (3) 79.3G6

343 339G17 332G24

(1) TQ MS (2) GIB MS (3) Review

(1) 1989MAG/DAV(b) (2) 1995RYA/FIE (3) 1996ARM/KIC

(1) O7 (2) 6.0G2.4 (1) !25 (2) 15.1G2.4 (1) 31.6G6 (2) 17.7G2.4 (1) 20G3 (2) 15.5G2.4 (1) 16G3 (2) 28.9G2.4 (1) 32G5 (2) 33.9G2.4

O29 25G10 !105 63G10 132G25 74G10 84G13 65G10 67G13 121G10 134G21 142G10

(1) KERD (2) CID

(1) 1989DEA/HAY (2) 2000ROD/ARM(b)

7G2

29G8

Review

1991ELL/SCH

(h5-C5H5)MnC(CO)x–CO xZ0 24.9G1.4 1 14.5G0.9 2 25.6G0.9

104.2G5.8 60.7G3.9 107.1G3.9

PES

2001LI/SZT

(L)(C6H6)MnC–CO LZnone CO (CO)2 (CO)3 (CO)4

30 25 12 21 10

126 105 50 88 42

Thermochemical

1985SIM/SCH

MnC 2 ðCOÞ10 ðHÞ–CO

19.1G1.7

80G7

CID

1991HOP/MCM

MnC(CO)x–CO xZ0 1 2 3 4 5

(CO)4Mn(CH3)HC–CO

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BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X Bonds

MnC 2 ðh xZ0 1 2 3 4 5 6 7 8 9

791

SiH2 ÞðCOÞx –CO 41.5 16.1 39.2 25.4 23.1 36.9 4.6 32.3 23.1 11.5

173.7 67.5 164.0 106.1 96.5 154.4 19.3 135.1 96.5 48.2

EI

1989STA/DOW

54.88G0.02 145.0G4.2

229.63G0.10 606.9G17.4

Derived

2001FU/RUS

(1) 26.5 (2) 28.5 (3) 29.1G1.4 (4) 32.5 (2) 17.8 (3) 21.5G1.2 (3) 25.9G1.4 (3) 11.8G1.2

110.9 119.2 121.8G5.9 136 74.5 90.0G5.0 108.4G5.9 49.4G5.0

CID

(1) 1989MAG/DAV(b) (2) 1989MAR/SQU (3) 1994DAL/HON (4) 2000VUK/STO

MnC–CH3OH –C2H5OH –(CH3)2CO –n-C3H7OH –(CH3)3CO –(CH3)3COH

32G7 34G7 39G7 35G7 39G7 38G7

134G29 142G29 163G29 146G29 163G29 159G29

Ion reactions

1984LAR/FRE

MnC–OC(CH3)2 –C(CD3)2

38.0G3.5 34.4G3.5

159G14 144G14

FT-ICR

1997LIN/CHE

MnC–S –CS

59G5.5 19G5.1

247G23 80.0G21

CID

2001RUE/ARM(b)

MnC–Se

39.5G12

165G50

Derived from IP in ref.

1996NIST

MnC–OTi (MnO)C–Ti

MnC(H2O)x–H2O xZ0

1 2 3

(continued)

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792

Comprehensive Handbook of Chemical Bond Energies

Table 17.1.2 (continued) BDEs of MnC–X Bonds

The broken bonds (boldfaceZdissociated fragment) MnC–NH2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

60.7G5

254G20

Ion reactions

1996ARM/KIC

(1) 36.9 (2) 35.1G1.9 (1) 34.2 (2) 36.3G2.9 (1) 11.8 (2) 15.3G2.4 (2) 8.6G1.4

154.4 147G8 143 152G12 49.4 64G10 36G6

CID

(1) 1989MAR/SQU (2) 1998WAL/ARM

MnC–pyridine –pyrimidine

43.6G2.1 38.2G2.3

182.6G8.6 159.9G9.7

CID

2000ROD/STA 2001AMU/ROD

MnC(pyrrole)x–pyrrole xZ0 1

42.4 27.0

177.4 113

Kinetics

2000GAP/YAN

MnC–adenine

52.5G1.9

219.8G8.1

CID

2002ROD/ARM

MnC–imidazole

51.2G1.1

214.2G4.4

CID

2004RAN/AMU

MnC–Si

O19G6.2

O79G26

Ion reactions

1995KIC/ARM

(CO)5MnC–SiMe3 –GeMe3 –SnMe3

24.0 16.1 15.9

100.3 67.5 66.6

Derived

1973BUR/STO

MnC–bipy, bipyZ2, 2 0 -bipyridine

74.0

309.7

Derived

2005TSI/DIE

MnC(NH3)x–NH3 xZ0 1 2 3

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BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X Bonds

MnC–phen, phenZ1, 10-phenanthroline

793

81.6

341.5

15G3 15G3 15G3 14G3

62.8G12.6 62.8G12.6 62.8G12.6 58.6G12.6

HP MS

1990BLA/JAY(b)

208.9

874.1

Derived

2005TSI/DIE

219.1

916.6

phenMn2C–bipy phenZ1,10phenanthroline, bipyZ2,2 0 -bipyridine

114.1

477.6

Derived

2005TSI/DIE

bipyMn2C–phen bipyZ2,2 0 -bipyridine phenZ1,10phenanthroline

125.4

524.9

Derived

2005TSI/DIE

Mn2C(H2O)x–H2O xZ8 9 10 11

Mn2C–bipy, bipyZ2, 2 0 -bipyridine Mn2C–phen, phenZ1, 10-phenanthroline

17.1.3 MnK–X bonds Table 17.1.3 BDEs of MnL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

MnK–H

O50.2G4.3

O210G18

Derived

1991ARM/SUN

(CO)4MnK(Cl)–Cl (CO)4MnK(Br)–Cl

70.3 70.3

294.1 294.1

Kinetics

1989JON/MCD

(continued)

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794

Comprehensive Handbook of Chemical Bond Energies

Table 17.1.3 (continued) BDEs of MnK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(CO)3MnK(h3-C3H5)–Cl 70.3

294.1

Kinetics

1989JON/MCD

(CO)4MnK(Cl)–Br (CO)4MnK(Br)–Br

70.6 70.6

295.4 295.4

Kinetics

1989JON/MCD

(CO)4MnK(Cl)–I (CO)4MnK(Br)–I

55.0 55.0

230.1 230.1

Kinetics

1989JON/MCD

(CO)3MnK(h3-C3H5)–I

57.2

239.3

Kinetics

1989JON/MCD

MnOK 3 –O

90.9G5.3

380G22

Derived from DfH0 in ref.

1996NIST

(1) (2) (1) (2) (1) (2)

117G25 119G13 151G25 172G13 188G25 170G16

CID

(1) 1992SUN/SQU (2) 1993SUN/WAN

179G14 116G11

CID

1999SUN/SQU

MnK(CO)x–CO xZ2 3 4

(h5-C5H5)MnK(CO)x– CO xZ0 1

28G6 28.4G3.0 36G6 41.1G3.0 45G6 40.6G3.9

42.8G3.3 27.7G2.6

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BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X Bonds

795

17.2 Tc–X and TcC–X bonds 17.2.1 Tc–X bonds Table 17.2.1 BDEs of Tc–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Tc–Tc

(1) 78.9 (2) 67.6

330 283

Correlation

1986MOR

(CO)5Tc–Tc(CO)5

42.4G0.5

177.5G1.9

MS

1970JUN/SVE

Tc–O –C

131 134.8G6.9

548 564G29

Review

1990SIM/BEA

17.2.2 TcC–X bonds Table 17.2.2 BDEs of TcD–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(CO)5TcC–Tc(CO)5

42.2G1.2

176.6G4.8

MS

1970JUN/SVE

TcC–H

47.2

197.5

Review

1990OHA/GOD

TcC–CH2 –C2H2 –C2H4

(1) (1) (1) (2) (1) (1) (1) (1) (1)

!464 !320 137–280 108.8 137–290 !295 O245 O280 O250

(1) ICR

(1) 2004GON

(2) Review

(2) 1998SCH/SCH

–C3H4 –C3H6 –C4H6 –C5H6 –C6H6

!111 !76.4 32.7–67 26 32.7–69.2 !70.5 O58.5 O67 O59.7

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 17.2.2 (continued) BDEs of TcC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

TcC–O

O40

O167

ICR

2004GON

Tc2C–CH2 –C6H6

!111 O59.7

!464 O250

ICR

2004GON

17.3 Re–, ReC–, and ReK–X bonds 17.3.1 Re–X bonds Table 17.3.1 BDEs of Re–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Re–Re

(1) 92G23 (2) 103.2G7.1

386G96 432G30

(1) Correlation (2) Spectroscopy

(1) 1986MOR (2) 1994HU/DON

(CO)5Re–Re(CO)5

(1) 51 (2) 44.7

214 187

(1) MS (2) Calorimetry

(1) 1970JUN/SVE (2) 1983ALT/CON

Re(111, surf.)–ReSi

17.3

72.4

FIM

1985WRI/HER

(CO)5Re–Mn(CO)5

(1) 50.3G2.3(2) (2) 35.6G2.6

210G9.6 149G11

(1) MS (2) Derived

(1) 1970JUN/SVE (2) 1992CON

Re(100, surf.)–K

68.4G0.1

286.2G0.4

TPD

1997VER/ZHA

Re(1000, surf.)–La –Ce –Pr –Nd

138.1G4.6 140.7G4.6 119.9G6.9 103.8G4.6

578.9G19.3 588.5G19.3 501.7G28.9 434.2G19.3

TD

1975ION/MED(b)

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BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X Bonds

–Sm –Eu –Gd –Tb –Ho –Er –Tm –Lu

797

99.2G6.9 87.6G4.6 119.9G6.9 108.4G4.6 113.0G6.9 115.3G4.6 80.7G6.9 106.1G6.9

414.9G28.9 366.6G19.3 501.7G28.9 453.5G19.3 472.8G28.9 482.4G19.3 337.7G28.9 443.8G28.9

(CO)5Re –Co(CO)5

27.0G3.6

113G15

Derived

1992CON

Re(1000, surf.)–Cu

w47.8

w200

TDS

1999WAG/SCH

(CO)5Re–H

(1) 74.7 (2) 69 (3) 74.8

312.5 289 313

(1) Electrochemical (2) Derived (3) Review

(1) 1991PAR/HAN (2) 1992MIL/MIL (3) 2001TIL

(CO)5Re–Cl –Br

75.0G4.5 67.6G2.6

314G19 283G11

Calorimetry

1983ALT/CON

Re–O

150G20

627G84

Review

1990SIM/BEA

Re(111, surf.)–O Re(100, surf.)–O Re(110, surf.)–O

125.0 131.3 135.0

523.0 549.4 564.8

Review

2003ZEI

(h5-C5Me5)ReO2–O

116.8G1.2

488.7G5

Calorimetry

1996GAB/JUL

Re(1000, surf.)–S

18.2 (phys)

76.2

STM

1993DUN/SAU

Re(1000, surf.)–S

(1) 104 (2) 95

435 397

(1) AES/TDS (2) Review

(1) 1988KEL/GEL (2) 1995SEE/ALL

Re(111, surf.)–N Re(100, surf.)–N Re(110, surf.)–N

142.0 149.1 153.4

594.1 623.8 641.8

Review

2003ZEI

(continued)

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798

Comprehensive Handbook of Chemical Bond Energies

Table 17.3.1 (continued) BDEs of Re–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Re(1000, surf.)–N

144

602

Review

1991BEN

Re(polycs. surf.)–H2

27.5 (phys)

115

TDS

1976DUC/EHR

Re(polycs. surf.)–H2

(1) 66 (2) 67

276 280

TDS

(1) 1968POU/PRY (2) 1976DUC/EHR

Re(polycs. surf.)–D2

27.5 (phys)

115

TDS

1976DUC/EHR

Re(polycs. surf.)–D2

67

280

TDS

1976DUC/EHR

Re(polysc. surf.)–O2

(1) 175 (2) 126.8G3.5 (3) 127 (4) 85

732 531G14 531 356

(1) Calorimetry (2) TDS (3) TDS (4) Review

(1) 1960BRE/HAY(b) (2) 1968GRE/STI (3) 1976WEB/ALN (4) 1982RAO/KAM

Re(polycs. surf.)–N2

67–74

280–309

TD

1969YAT/MAD

Re(1000, surf.)–N2

8 (phys)

33.5

Review

1991BEN

Re(polycs. surf.)–CO

24 (phys) 29

100 122

TD

1969YAT/MAD

Re(polycs. surf.)–CO

(1) 54 (2) 47 (2) 57 (2) 63

226 197 239 264

TDS

(1) 1967GAS/THW (2) 1969YAT/MAD

Re(polycr. surf.)–CO

28 (phys)

117

TDS

1974ALN/EHR

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BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X Bonds

799

Re(polycr. surf.)–CO

64.5

270

TDS

1974ALN/EHR

Re(0001, surf.)–CO

27

113

TPD

1977HOU/DUC

Re(10–10, surf.)–CO

23–28 (a-states) 44–50 (b-states)

95–118 185–210

LEED

2004PAU/PRZ

(CO)5Re–CH3

52.6G1.9

220G8

Calorimetry

1983ALT/CON

23.9G0.9 24.0G0.9

100.0G3.8 100.4G3.8

Kinetics

2003BEN/MEZ

(L)Re(CO)2–THF LZTp Tp* TpZhydridotris(pyrazolyl)borate Tp*Zhydridotris(3,5 dimethylpyrazolyl)borate THFZtetrahydrofuran

Re(100, surf.)–NH3

3.4G0.6 (phys.) 14.2G2.5

TPD

1993ROS/FAR

Re(1000, surf.)–NH3

21

87.9

TPD

1990ROS/ASS

(CO)5Re–SiMe3 –GeMe3 –SnMe3

71.5G2.3 73.8G2.3 85.3G2.3

299.1G9.6 308.7G9.6 357.0G9.6

Derived

1975BUR/STO

17.3.2 ReC–X bonds Table 17.3.2 BDEs of ReD–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(CO)5ReC–Re(CO)5 –Mn(CO)5

45.7G1.2 54.4G1.2

191G5 228G5

MS

1970JUN/SVE

ReC–H

53.7G1.6

224.7G6.7

GIB

2004ARM/LI

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 17.3.2 (continued) BDEs of ReC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

Methods (reference in parentheses)

kcal/mol

kJ/mol

ReC(CH3)(CO)5–H

(1) 73G3 (2) 70.3G3.1

305.4G12.6 294G13

(1) Thermochemical (2) Review

(1) 1981STE/BEA (2) 1990SIM/BEA

ReC 2 ðCOÞ10 –H

58.8G1.7

246G7

Review

1990SIM/BEA

MnReC(CO)10–H

!63.8G1.7

!267G7

Review

1990SIM/BEA

(L)(CO)2ReC–H LZPMe2Ph PMe3

71.0

297.1

Electrochemical

1996WAN/ANG

71.8

300.4

ReC–C –CH

119.0G0.9 134.7G1.4

497.7G3.9 563.5G5.8

GIB MS

2004ARM/LI(b)

ReC–CH2

(1) 102G9 (2) 88.4–111 (3) 95.5G1.4

427G38 370–464 399.4G5.8

(1) ICR (2) ICR (3) GIB MS

(1) 1991IRI/BEA (2) 2003GON (3) 2004ARM/LI(b)

ReC–CH3 –CH4

51.2G3.0 12.2G3.5

214.2G12.5 51.1G14.5

GIB MS

2004ARM/LI(b)

ReC–C2H4

30

125.5

Review

1998SCH/SCH

ReC–C3H4 –C3H6

O70.5 O69

O295 O289

ICR

2003GON

ReC(O)x–CH2 xZ1 2

O110 O118

O460 O494

ICR

2003GON

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References

BDEs of Mn(MnG)–, Tc(TcC), and Re(ReG)–X Bonds

ReC(O)x–O xZ0

801

(1) 102G17 (2) 104G14 (2) !118 (2) 122G4

427G71 435G59 !494 510G17

ICR

(1) 1991IRI/BEA (2) 1996FIA/KIH

w20

w84

Kinetics

2001ARI/NEW

(CO)5ReC–SiMe3 –GeMe3 –SnMe3

16.1 39.2 39.2

67.5 164 164

Derived

1977BUR/STO

Re2C–C3H6

O69

O289

ICR

2003GON

1 2

O

O N O

Re O

+ O N O

17.3.3 ReK–X bonds Table 17.3.3 BDEs of ReL–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

References

kcal/mol

kJ/mol

(CO)4(Cl)ReK–Cl –Br –I

79.2 70.6 57.2

331.4 295.4 239.3

Kinetics

1989JON/MCD

(CO)3(h3-C3H5)ReK–Cl –Br –I

82.8 70.6 57.2

346.4 295.4 239.3

Kinetics

1989JON/MCD

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chapter eighteen

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X bonds 18.1 Fe–, FeC–, and FeK–X bonds 18.1.1 Fe–X bonds Table 18.1.1 BDEs of Fe–X Bonds

The broken bonds (boldfaceZdissociated fragment) Fe–Fe

Fe(Fe)x–Fe xZ1 2 3 4 5 6 7 8 9 10

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(1) (2) (3) (4) (5)

25G5 30.3 27.4G2.1 21.6 28.2

105G21 127 114.7G8.7 90.6 118

(1) (2) (3) (4) (5)

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1)

44.0 50.4 51.9 73.1 71.9 53.8 67.4 66.0 74.3 81.3

184 211 217 306 301 225 282 276 311 340

(1) Review

MS PD CID Review Review

References (1) (2) (3) (4) (5)

1969LIN/KAN 1986BRU/ZHE 1988LOH/LIA 1996SMI/YAT 2001ARM

(1) 2001ARM

(continued)

803

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804

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.1 (continued) BDEs of Fe–X Bonds

The broken bonds (boldfaceZdissociated fragment) 11 12 13 14 15 16 17 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (1) (1) (1) (1) (1) (1) (2) (3)

99.7 69.3 86.8 77.9 74.1 72.2 84.1 98.7 w83.6

kJ/mol 417 290 363 326 310 302 352 413 w350

Methods (reference in parentheses)

References

(2) Review (3) Extrapolate

(2) 1994ARM/HAL (3) This volume

Cl2Fe–FeCl2 Br2Fe–FeBr2

35G3 40G4

146G13 167G17

Review

1970DAR

F3Fe–FeF3

48.0

201

MS

1986SID/BOR

(CO)4Fe–Fe(CO)5

41.0

171.5

LP

1988SMI

R(CO)2Fe–Fe(CO)2R RZ(h5-C5H5) R(CO)3Fe–Fe(CO)3R RZ(C3H5)

25

104.6

Review

1994NOL

13.5

56.5

Fe(100, surf.)–Fe

(1) 10.4G1.8 (2) w12

43.4G7.7 w48

STM

(1) 1993STR/PIE (2) 1994STR/PIE

Fe(polycr. surf.)–K

54.0

225.9

TDS

1986ALB

Fe(110, surf.)–K

(1) (2) (1) (2) (1)

238.5G8 255.2 225.9G8 217.6 217.6G8

TDS

(1) 1981LEE/WEI (2) 1986ALB

Fe(100, surf.)–K Fe(111, surf.)–K

57G2 61.0 54G2 52.0 52G2

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BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

805

Fe–Cr

w18

w75

Fe–Au

44.7G4.6

187.0G19.3 Review

1986MOR

(1) (2) (3) (4) (5) (6)

29.6G3 43G6 45.7G3.0 37.5G1.9 35.4G0.8 O74.8

124G13 180G25 191.2G12.6 156.9G7.9 148G3 O313

(1) (2) (3) (4) (5) (6)

(1) (2) (3) (4) (5) (6)

(1) (2) (1) (3) (4) (5)

R60G12 62G2 %70G14 67.6 65.0 67.6

R251G150 259.4G8.4 %293G59 282.8 272 283

(1) Review (2) TR-IR

(1) 1991MIL/BEA (2) 1996WAN/NAR

(3) Electrochem. (4) Review (5) Review

(3) 1991PAR/HAN (4) 1994NOL (5) 2001TIL

Fe(H)x–H xZ0

2

(CO)4Fe(H)x–H xZ0 1

Spectroscopy

Ion reactions Ion reactions GIB MS GIB MS Review Derived

2003LU/ZHA

1985SAL/LAN 1986TOL/BEA 1988SCH/ELK 1990SCH/ARM 1996ARM/KIC 1991ARM/SUN

(h5-C5H5)(CO)2Fe–H

(1) 57.1 (2) 58.0 (3) 57.1

238.9 242.7 239

(1) Electrochem. (2) Review (3) Review

(1) 1991PAR/HAN (2) 1994NOL (3) 2001TIL

Fe(100, surf.)–H

(1) 63.6 (2) 59.5G2

266 248.9G8.4

(1) TPD (2) Thermochem.

(1) 1977BOZ/ERT (2) 1992BUR/MAD

Fe(110, surf.)–H Fe(111, surf.)–H

64.6 62.1

270.5 260

TPD

1977BOZ/ERT

Fe(211, surf.)–H

63.0

263.5

TPD

1995SCH/PEC (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 18.1.1 (continued) BDEs of Fe–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References (1) 2003SCH/SCH

(2) 83.4G4.7

(1) Derived from DfH0 in ref. 348.9G19.7 (2) Derived

(GaAs, crystal)Fe–H

19.1

80.1

DLTS

1996RAD/CON

Fe(F)x–F xZ0 1 2

106.9 123.5 122.1

447 517 511

Derived from DfH0 in ref.

1996NIST

(1) 59G23 (2) 78.8G1.6 (3) 68.3

247G96 329.7G6.7 286

(1) 1968GAY (2) 1995HIL (3) 1996NIST

(3) 122.7 (3) 55.8

513 233

(1) Spectroscopy (2) MS (3) Derived from DfH0 in ref.

Fe–Br

58G20

243G84

Review

1974GUR/KAR

Fe(I)2–I

(1) 23 (2) 29.5

96 123

(1) Review (2) Derived from DfH0 in ref.

(1) 1970DAR (2) 1996NIST

(1) (2) (3) (4) (5) (6)

405.0G7.7 402.3G7.7 428G15 402.2G5.8 407.0G1.0 O467G15

(1) (2) (3) (4) (5) (6)

(1) (2) (3) (4) (5) (6)

(FeO)–H

Fe(Cl)x–Cl xZ0

1 2

Fe(Fe)x–O xZ0

1

(1) 80.9G4

96.8G1.8 96.2G1.8 102.3G3.7 96.1G1.4 97.3G0.2 O111.6G3.7

338G17

MS Spectrometry Review Derived PD GIB MS

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(2) This volume

1984SMO/DRO(b) 1989MER 1996ARM/KIC 2005MET/NIC 2005CHE/PAR 1989LOH/LIA

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

807

PFe(II) O

65–85

272–356

Derived

2005ROS/PIS

Fe(polysc. surf.)–O

w118

w494

Calorimetry

1987PRI/BAU

Fe–S

(1) 77.2G3.5 (2) 78.6G3.5

323.0G14.6 (1) MS 328.9G14.6 (2) CID

Fe(100, surf.)–N

21.2G0.9 (phys) 88.8G3.9

STM

2000BAR

Fe(100, surf.)–N Fe(110, surf.)–N Fe(111, surf.)–N

142 141 138

594 590 577

Review

1991BEN

Fe–C

(1) 81.7G4.6 (2) 89.9G6.9

341.8G19.3 Derived 376.3G28.9

(1) 1997ANG/BER (2) 1997BRU/MOR

Fe–Si

71G6

297G25

MS

1969MAH/MCL

Fe–Ge

50.4G7

210.9G29

MS

1968KAN/STR

Fe–H2 –HD –D2

O22 O22 O22

O92 O92 O92

Est. by exp.

1984HAL/KLE

Fe(polycr. surf.)–H2

(1) (2) (3) (4) (5) (4)

142 150 84.9 98 97 104

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

PFe(IV)

O

PZporphyrin

–D2

34 36 20.3 23.4 23.2 24.9

Calorimetry Calorimetry FDMS Calorimetry Calorimetry

(1) 1967DRO/PAT (2) 2002KOS/SCH(b)

1953WAH/KEM 1955BAG/TOM 1972CHO/COU 1978WED/GEU 1991ZOM/RAN (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 18.1.1 (continued) BDEs of Fe–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Fe(100, surf.)–H2

20.7

86.6

TPD

1980BEN/MAD

Fe(110, surf.)–H2

26

109

Review

1978MAD/BED

Fe(110, surf.)–D2

14.0

58.8

Mol. beam

1985KUR/HUD

Fe–O2

O47.3

O198

TR LIF

1999PLA/ROL

Fe(polycr. surf.)–O2

(1) (2) (3) (4) (5)

568 502 569 534 490

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Fe(111, surf.)–O2

w119.5

w500

TDS

1992GAN/KIE

(1) (2) (3) (4)

321.7G16.7 345.8G17 343 335G13

(1) (2) (3) (4)

(1) (2) (3) (4)

Fe(OH)x–OH xZ0

1

Fe(CO)x–CO xZ0

1 2 3

135.8 120 136 128 117

76.9G4 82.6G4.1 82 80.1G3

Calorimetry Calorimetry Calorimetry Review Calorimetry

MS MS Derived Derived from DfH0 in ref.

(4) 111.9G4

468G17

(1) (2) (3) (1) (2) (1) (2) (1) (2)

97G29 (1) PES 33.9G14.6 (2) CID 43.9G7.5 (3) PES 97G29 153.6G14.6 135G29 121.8G24.3 19G39 116.7G36.8

23.1G6.9 8.1G3.5 10.5G1.8 23.1G6.9 36.7G3.5 32.3G6.9 29.1G5.8 4.6G9.2 27.9G8.8

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1960BRE/HAY 1961WED 1965BRE/HAY 1982RAO/KAM 1992GAN/BOR

1980MUR 1990GOR/MIL 1994HIL/LAU(b) 2003SCH/SCH

(1) 1979ENG/LIN (2) 1992SUN/WAN (3) 1993VIL/LEO

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

4

(1) 55.3G11.5 (3B2 Fe(CO)4) (4) 48G4 (5) 41.5G2 (1A1 Fe(CO)4) (6) w42

231G48

Fe(C2H2)(CO)4–CO

809

200.8G16.7 (4) LP 173.6G8.4 (5) LP

(4) 1981SMI/LAL (5) 1984LEW/GOL

w176

(6) Review

(6) 2004DAM

21.0G0.5

88G2.3

Kinetics

1998PEA/COO

Fe(CO)3(PR3)–CO RZMe Et

O40.9 O39.2

O171 O164

PAC

1993NAY/BUR

Fe(CO)2(PMe3)–CO

O29.8

O125

PAC

1993NAY/BUR

Fe(CO)3(PPh3)–CO

!42.5G1.2

!177.8G5

Kinetics

1967SIE/ANG

Fe(CO)2(dmpe)–CO, dmpeZ1,2-bis (dimethylphosphino)ethane

O36.1

O151

PAC

1993NAY/BUR

Fe(polycr. surf.)–CO

(1) (2) (3) (4)

134 192 155 210

Calorimetry

(1) (2) (3) (4)

Fe(100, surf.)–CO

12.8 (phys)

54

TPD

1987MOO/BER

Fe(100, surf.)–CO

(1) 25.1 (2) 26.2 (3) 26.3

105 110 110.0

(1) TDS (2) TPD (3) TPD

(1) 1980BEN/MAD (2) 1987MOO/BER (3) 1988CAM/DWY

Fe(110, surf.)–CO

(1) 35.9 (2) 37

150 155

(1) LITD (2) Review

(1) 1982WED/RUH (2) 1990CAM(b)

32 46 37 50

1955BAG/TOM 1965BRE/HAY 1987WED 1992GAN/KIE

(continued)

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810

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.1 (continued) BDEs of Fe–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Fe(111, surf.)–CO

(1) 20G5 (2) 24

84G21 100

(1) TPD (2) Calorimetry

(1) 1989WHI/RIC (2) 1993WED/GAN(b)

Fe(111, surf.)O–CO

50.2

210

TDS

1992GAN/KIE

FePPIX–CO FePPIXZprotoheme

2.6G0.5

11G2

FT IR

2005YE/YU

Myoglobin–CO

(1) 4.3G0.5 (2) 4G3

18G2 16.7G12.6

(1) Pulsed LP (2) Review

(1) 1992TIA/SAG (2) 2006MIK/YOM

Fe–CO in myoglobin

34G4

142.3G16.7 PD

2005WAL/RAI

Fe(polycr. surf.)–CO2

(1) 68 (2) 67 (3) 71.7

285 280 300

Calorimetry

(1) 1965BRE/HAY (2) 1987WED (3) 1993WED/GAN

Fe(CO)3(N2)–N2 Fe(CO)4–N2

9.0G4.6 17.6G1.8

37.7G19.2 73.6G7.5

RT-IR

2001WAN/LON

Fe(polycr. surf.)–N2

(1) 10 (phys) (2) 5!

42 21!

Calorimetry

(1) 1950BEE/COL (2) 1975WED/BOR

Fe(polycr. surf.)–N2

(1) 40 (2) 70

167 293

Calorimetry

(1) 1950BEE (2) 1955BAG/TOM

Fe(100, surf.)–N2

!7.5 (phys)

!31

TDS

1982ERT/LEE(b)

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BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

811

Fe(100, surf.)–N2 Fe(110, surf.)–N2

58 50

243 209

TDS

1977BOZ/ERT(b)

Fe(111, surf.)–N2

(1) 7.5 (phys) (2) w7.4

31.4 w31

(1) TDS (2) UPS

(1) 1982ERT/LEE (2) 1984GRU/GOL

Fe(111, surf.)–N2

51

213

TDS

1977BOZ/ERT(b)

FeO(111, surf.)–H2O Fe3O4(111, surf.)–H2O

12.4G0.5 12

52G2 50

TDS

2002WEI/RAN

Fe–NH3

(1) 7.5G1 (2) 20.3G0.5

31.4G4.2 84.9G1.9

(1) MPI (2) FTR

(1) 1990MIT/HAC (2) 1993PAR/RIL

Fe(polycr. surf.)–NH3

44.9

188

Calorimetry

1953WAH/KEM

Fe–CH2 –CH3

(1) 87G7 (2) 32.3G7

364G29 135G29

(1) PA (2) Review

(1) 1989JAC/GOR (2) 1996ARM/KIC

Thermolysis

1996RIO/HAL

(1) LP (2) Review

(1) 1988SMI (2) 1990SIM/BEA

(L)(OEP)Fe–CH3 OEPZoctaethyl porphyrinato LZnone Pyridine PEt3

Fe(CO)4–C2H4

21 20 18

88 84 75

(1) 37.2 (2) 36.3G4.3

155.6 152G18

(continued)

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812

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.1 (continued) BDEs of Fe–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Fe(C2H4)(CO)3–C2H4

(1) R27G6 (2) 21.3G2

R113G25 89.1G8

Equilibrium

(1) 1987MIL/GRA (2) 1997HOU/WEI

Fe(polycr. surf.)–C2H4

68

284

Calorimetry

1950BEE/COL

Fe(100, surf. H2)–C2H4

8.5G2.0

36.0G8.4

TPD

1991BUR/MAD

Fe(C2F4)(CO)3–C2F4

R22

R92

Est. by exp.

1997HOU/WEI

Fe(C2Cl4)(CO)3–C2Cl4

R22

R92

IR

2000CED/WEI

Fe(110, surf.)–C2Cl4

12.7G2.6

53.1G10.9

TPD

1989SME/CHE

Fe(100, surf.)–C2H5

38G4

159G16.7

Thermochemical

1992BUR/MAD

(OEP)Fe–C2H5 OEPZoctaethyl porphyrinato

17

71

Thermolysis

1996RIO/HAL

Fe–C3H5 –C3H6

52 19

218 79

Review

2003CED/WEI

Fe(CO)5–Ni(CO)4

9.0

37.7

Equilibrium

1983BAE/FED

Fe(CO)5–(h3-C3H5)

42.1

176

Review

1992CON

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BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

813

Fe(C3H6)(CO)3–C3H6

w19

w79.5

Est. by exp.

1995LON/WAN

(OEP)Fe –CH2C(CH3)3 OEPZoctaethyl porphyrinato

15

63

Thermolysis

1996RIO/HAL

(1) 67G5 (2) 91.4G3.0

280G21 (1) Review 382.4G12.6 (2) VLPP

(1) 1990PUT/SMI (2) 1984LEW/SMI

Fe(1-C5H10)(CO)3 –(1-C5H10)

20.2G0.7

84.5G3

TR-IR

2000LON/WEI

Fe(DMB)(CO)3–DMB DMBZ3,3-dimethyl -1-butene

15.2G3.8

63.6G15.9

TR-IR

2001WAN/WEI

(OEP)Fe–C6H5 OEPZoctaethyl porphyrinato

31

130

Thermolysis

1996RIO/HAL

Fe–C6H6

O16.1

O67.5

Derived

2001PAN/RAO

(h5-C5H5)(CO)2 Fe–CH2C6H5

28

117

Thermolysis

1992MAN/HAL

FeO(111, surf.) –C2H3C6H5

13.1 (phys)

55

TDS

2002WEI/RAN

FeO(111, surf.) –C2H5C6H5

10.5–12.4 (a-state) 13.1–13.7 (b-state)

44–52

TDS/UPS

1998ZSC/RAN

Fe(h5-C5H5)x –(h5-C5H5) xZ0 1

55–58 (continued)

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814

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.1 (continued) BDEs of Fe–X Bonds

The broken bonds (boldfaceZdissociated fragment)

(h5-C5H5)(CO)2 Fe–Si(CH3)3 (h5-C5H5)(CO) (PMe3)2Fe–SiMe3

(h-C5H5)(CO)2Fe –SnMe3 –SnPh3 –SnCl3

(h5-C5H5)(CO)2Fe –U(h5-C5H5)3

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

20.3–21.7 (g-state)

85–91

45.4

190.1

51.4

215.2

(1) (1) (2) (1)

53.0 59.5 54G9 70.6

30.9G3

AcMP8–(CH3)2SO 18.7 16.0 –HO(CH2)2SCH3 AcMP8Zferric N-acetyl-microperoxidase-8

Methods (reference in parentheses)

References

MS

1978SPA

221.9 248.9 226G38 295.2

MS

(1) 1978SPA

129.3G13

Review

1994NOL

78.2 66.9

Spectrometry

2003LUS/COW

(2) 1974CLA/RAK

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BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

815

18.1.2 FeC–X bonds Table 18.1.2 BDEs of FeD–X Bonds

The broken bonds (boldfaceZdissociated fragment) FeC–Fe

FeC(Fe)x–Fe xZ1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 N

(S)FeC(Fe)x–Fe xZ0 1 2 3

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(1) (2) (3) (4) (5)

63.6G1.6 62G5 63.2 62.2G3.0 65.0

266.2G6.8 259G21 264 260.4G12.5 272

(1) (2) (3) (4) (5)

(1) (2) (2) (2) (1) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (3) (4)

29.3 40.4 51.6 62.1 27.0 75.3 76.5 60.2 67.2 67.9 73.6 79.8 97.5 67.2 90.1 76.2 77.2 74.3 89.1 98.7 w83.6

123 169 216 260 113 315 320 252 281 284 308 334 408 281 377 319 323 311 373 413 w350

(1) PD (2) CID

(1) 1987HET/FRE (2) 2000MAR/SUG

(3) Review (4) Extrapolate

(3) 1994ARM/HAL (4) This volume

90.4G2.8 57.0G4.2 59.5G6.7 65G11

CID PD Derived CID Review

378.2G11.6 CID 238.3G17.4 249G28 272G47

References (1) (2) (3) (4) (5)

1988LOH/LIA 1987HET/FRE 1996SMI/YAT 2000MAR/SUG 2001ARM

2002KOS/SCH(b)

(continued)

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816

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(S2)FeC(Fe)x–Fe xZ0 1

106.8G7.6 81G11

447G32 338G44

CID

2002KOS/SCH(b)

FeC(Cl)x–Fe xZ1 2 3 4 5 6

95 79 56 57 63 15

397 331 234 238 264 63

Derived

2001SCH/LOO

FeC(O)–Fe

O117G8

O490G34

FT-MS

1986JAC/FRE(b)

FeC(O)–Co

O117G8

O490G34

FT-MS

1986JAC/FRE(b)

FeC–Mg

O32G2

134G8

Est. by exp.

1991ROT/FRE

FeC–La

101G5

423G21

Ion reactions

1988HUA/FRE

FeC–Sc –Ti –V –Nb –Ta –Cr –Co –Ni

79G5 84G6 101G5 91G5 72G5 75G7 62G5 69G5

331G21 351G25 423G21 381G21 301G21 314G29 259G21 289G21

Derived

1987HET/FRE

FeC–Cu –Ag

56G7 53G7

230G29 222G29

(1) Derived (2) FT-ICR

(1) 1987HET/FRE (2) 1991NG/GOR

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BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

817

FeC–Ar

(1) 12.3 (2) 3.4G1.8

51 14.2G7.7

(1) GDMS (2) CID

(1) 1995BAR/SMI (2) 2001TJE/WAL

FeC–Kr

8.0G1.6

33.5G6.7

CID

2001TJE/WAL

FeC–Xe

(1) (2) (3) (4)

10.0G1.4 11.7G1.8 11.7G1.5 11.0G1.4

41.8G6 49.0G8 49.0G6.3 46.0G5.8

(1) (2) (3) (4)

(1) (2) (3) (4)

1995KHA/STE 1997TJE/ARM 1997DIE/HAR 2001TJE/WAL

FeC–H

(1) (2) (3) (4) (5)

59G5 58G2 48.9G1.4 47.6 50.5G2.3

247G21 242.7G8 204.6G6 199 211.2G9.6

Ion reactions

(1) (2) (3) (4) (5)

1984HAL/KLE 1985CAS/FRE 1986ELK/ARM 1993EKE/HAG 2005LIY/ARM

FeC(O)–H

(1) 106G4 (2) 107

444G17 448

(1) Thermochem. (2) Est. by exp.

(1) 1986KAN/BEA (2) 1986CAS/FRE

(1) (2) (1) (1) (1) (1)

295 120G23 266 313 313 297

(1) MS (2) GIB MS

(1) 1993EKE/HAG (2) 1996TJE/ARM

FeC(CO)x–H xZ1 2 3 4 5

70.6 28.6G5.5 63.6 74.8 74.8 71.0

CID CID Equilibrium CID

FeC(H2O)–H

51.4G3.5

215G14

GIB MS

1996TJE/ARM

FeC(C)–H FeC(CH)–H

88G10 82G5

368G42 343G21

Ion reactions

1986HET/FRE

FeC(h5-C5H5)–H

46G5

193G21

Ion reactions

1996BAK/JAC (continued)

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818

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment) (L)(CO2)2FeC–H LZ(CO)3 (h5-C5H5)(CH3)

(L)FeC–H LZ(h5-C5H5)2

(h5-C5H8)

(L)(CO)3FeC–H LZ(PPh3)2 (PMePh2)2 (PMe2Ph)2 (PMe3)2 Ph2P(CH2)3PPh2 Ph2P(CH2)PPh2

FeC(Fe)x–D xZ0 1 2 3 4 5 6

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) (2) (1) (2)

74G5 71.5G3.6 53G3 50.2G3.3

310G21 (1) Thermochem. 299G15 (2) Review 221.8G12.6 210G14

(1) 1981STE/BEA (2) 1990SIM/BEA

(1) (2) (3) (4)

54G5 51.4G5 50.4G2.6 46G5

226G21 215G21 211G11 192G21

(1) (2) (3) (4)

(1) (2) (3) (4)

60.1 62.2 64.9 66.1 61.5 66.5

251.5 260.2 271.5 276.6 257.3 278.2

Electrochemical

1996WAN/ANG

(1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (1) (2)

208 227 140 154 171 204 208 205 183 220 264 244 204 202

(1) Review (2) Re-evaluated

(1) 2001ARM (2) 2003LIY/GRI

49.7 54.2 33.5 36.9 40.9 48.7 49.7 48.9 43.7 52.6 63.1 58.3 48.8 48.2

Thermochem. Review Re-evaluated Photodissociation

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

1981STE/BEA 1990SIM/BEA 1992RIC 1990HUA/FRE

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

7 8 9 10 11 12 13 14

(1) (2) (1) (2) (1) (1) (1) (1) (2) (1) (1)

45.4 52.3 55.0 57.7 61.9 58.1 58.6 58.1 62.0 58.1 66.2

819

190 219 230 241 259 243 245 243 260 243 277

FeC(CO)–D FeC(H2O)–D

31.1G1.8 52.1G2.8

130G8 218G12

GIB MS

1995TJE/ARM

FeC–F

(1) (2) (3) (3) (4) (3) (4) (5)

406G33 360–423 O343 O293 O289 O239 O297 251G29

(1) Knudsen cell (2) FT-ICR (3) GIB MS

(1) 1985GOR/RYZ (2) 1992SCH/HRU (3) 1989FIS/SCH

(4) Ion reactions

(4) 1979ALL/RID

(5) High tem. MS

(5) 1984GRA/ROS

69.0

Equilibrium

(1) 1995BUS/KEM

–Cl –Br –I

FeC(H2)x–H2 xZ0

1 2 3 4 5 6

FeC–C

97G8 86–101 O82 O70 O69 O57 O71 60G7

(1) 16.5 (lowest configur.) (2) 10.8G0.6 (1) 15.7G0.7 (2) 17.0 (1) 7.5G0.4 (2) 9.6 (1) 8.6G0.4 (2) 9.6 (1) 2.2G0.3 (2) 4.3 (1) 2.3G0.3 (2) 4.0 (2) 0.8

45.2G2.5 65.7G2.9 71.1 31.4G1.7 40.2 36.0G1.3 40.2 9.2G1.3 18.0 9.6G1.3 16.7 3.3

(2) 1999BOW/KEM

(1) 94G7 (2) 85.1G4.1

393G21 PD 356.1G17.2

(1) 1986HET/FRE (2) 1997ANG/BER (continued)

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820

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment) FeC(Fe)x–C xZ1 2 3 4 5 6 7 8 9 10 11 12 13 14

FeC–CH –CH2

–CH3

–CF2

FeC(Fe)x–CD xZ1 2 3 4 5 6

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

95.2G6.9 122.4G3.2 134.7G0.9 135.6G1.2 133.5G2.3 124.5G3.5 129.8G3.5 135.1G3.7 138.1G4.2 139.5G4.6 136.5G4.2 141.8G5.1 143.9G4.8 138.4G6

398.5G28.9 GIB MS 512.3G13.5 563.5G3.9 567.3G4.8 558.6G9.6 521.0G14.5 543.1G14.5 565.4G15.4 577.9G17.4 583.7G19.3 571.2G17.4 593.4G21.2 602.1G20.3 578.9G25

2001LIY/ZHA

(1) (1) (2) (3) (4) (1) (3) (5) (6) (7) (8)

423G29 343G29 346G6 341G4 %342G2 272G21 229G5 !289 289G21 239G10 201G17

(1) PD

(1) 1986HET/FRE

(2) GIB MS (3) Review (4) Photofrag.

(2) 1992SCH/ARM(b) (3) 1996ARM/KIC (4) 2000HUS/AGU

(5) (6) (7) (8)

(5) (6) (7) (8)

101G7 82G7 82.6G1.5 81.5G1 %81.7G0.5 65G5 54.7G1.2 !69 69G5 57.1G2.3 48G4

70.1G3.0 117.8G2.3 117.6G6.9 121.3G5.1 123.1G3.9 112.5G5.5

Ion reactions Ion reactions GIB MS FT-ICR

293.3G12.5 GIB MS 493.0G9.6 492.1G28.9 507.5G21.2 515.2G16.4 470.8G23.2

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

1979ALL/RID 1984JAC/FRE(b) 1989FIS/SCH 1998CHE/AUB

2001LIY/ZHA

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

7 8 9 10 11 12 13 14

821

117.1G5.8 116.0G8.1 114.1G9.2 131.4G7.1 129.1G8.5 137.2G8.1 146.4G9 132.6G9.2

490.1G24.1 485.3G33.8 477.6G38.6 550G30 540.3G35.7 574.1G33.8 612.7G37.6 554.8G38.6

FeC(Fe)x–CD2 xZ1 2 3 4 5 6 7 8 9 10 11 12 13 14

52.8G3.5 68.5G2.1 80.7G2.1 78.4G2.1 w74 70.8G2.1 74.7G2.1 80.5G2.1 83.2G2.1 83.9G2.1 82.8G2.1 82.1G2.1 82.6G2.1 82.3G2.1

220.9G14.5 GIB MS 286.6G8.7 337.6G8.7 328.0G8.7 w310 296.2G8.7 312.6G8.7 336.7G8.7 348.3G8.7 351.2G8.7 346.4G8.7 343.5G8.7 345.4G8.7 344.4G8.7

2001LIY/ZHA

RhFeC–CH2

78–93

326–389

PD

1987HUA/BUC

FFeC–CF2

17.9–34

75–142

Ion reactions

1998CHE/FRE(b)

FeC(CH3)–CH3

O38.2

O160

Review

1990SIM/BEA

(L)FeC(CO)–CH3 LZCO H2O CH3

(1) 31.6G2.3 (1) 45.4G2.3 (2) 43.1G2.6

132G10 190G10 180G11

GIB MS

(1) 1996TJE/ARM

FeC(Fe)x–CD3 xZ0 1

54.7G4.2 43.6G3.7

228.7G17.4 GIB MS 182.4G15.4

(2) 1992SCH/ARM

2001LIY/ZHA (continued)

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

822

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment) FeC(CH4)x–CH4 xZ0 1 2 3 N

FeC–C2H2

–C2H3 –C2H5 –C2H6

–(CH3)2

FeC(C2H4)x–C2H4 xZ0

1

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) (2) (1) (2) (1) (2) (1) (2) (3)

13.7G0.8 17.5 23.3G1 26.0 23.6G1.4 5.2 17.6G1.4 w4.9 w2

57.3G3.3 73.2 97.5G4.2 108.8 98.7G5.9 21.8 73.6G5.9 w21 w8

(1) (2) (3) (4) (5) (5) (6) (7) (8) (5)

32G6 38.0G0.5 36G2 60.2G2.3 56.8G2.5 55.7G2.1 15.3G1.4 18G5 17.9G3 97.8G2.9

(1) (2) (3) (4) (5) (5)

34G2 35G5 34.5 39.9G1.4 34.6G2.5 36.2G3.7

Methods (reference in parentheses)

References

(1) CID (2) Equilibrium

(1) 19\93SCH/ARM (2) 2001ZHA/KEM(b)

(3) Extrapolate

(3) This volume

134G25 159.0G2.1 151G8 252G10 238G11 233G9 64G6 75G21 74.9G12.5 409G12

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

(6) Ion reactions (7) KERD (8) KERD

(6) 1992SCH/ARM (7) 1988HAN/BEA (8) 1995CAR/KOP

142.3G8.4 146.4G21 144.3 166.9G5.9 145G11 151G15

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

PD Ion reactions IRMPD Ion reactions Review

Ion reactions KERD Ion reactions Ion reactions GIB MS

1989MAC/JAC 1995SCH/SCH 1997SUR/RAN 1992SCH/ARM(b) 1996ARM/KIC

1983JAC/FRE 1989KOP/JAC 1995SCH/SCH 1996BAK/JAC 1998SIE/JAR

FeRhC–C2H2 FeLaC–C2H2

O24 O24

O100 O100

PD

1987HUA/BUC

FeRhC–C2H4

O45

O188

PD

1987HUA/BUC

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds FeLaC–C2H6

O33

O138

PD

FeC–C3H3 –C3H6

(1) (2) (3) (4) (4) (5) (6) (7)

385G63 166G6 154.8G1.3 145G7 133.1G4 154.8G8 155G21 356G21

(1) (2) (3) (4)

–C3H6(cyclo)

–C3H6 (metallocyclic) –C3H8

92G15 39.6G1.5 37.0G0.3 34.7G1.7 31.8G1.0 37G2 37G5 85G5

823

1987HUA/BUC

Ion reactions GIB MS FT-MS Review

(1) (2) (3) (4)

1989BUC/FRE 1992SCH/ARM(b) 1995SCH/SCH 1996ARM/KIC

(5) Ion reactions (6) KERD (7) KERD

(5) 1983JAC/FRE (6) 1989KOP/JAC (7) 1996FRE

(3) 17.9G1

75G4

FeLaC–C3H4 FeRhC–C3H4

O33 O33

O138 O138

PD

1987HUA/BUC

FeLaC–C3H8 –C4H8

O30 O30

O126 O126

PD

1987HUA/BUC

FeC–1,3-C4H6

(1) (2) (3) (3)

201G21 !234 181.6G4.2 163.6G2.1

(1) PD (2) FT-MS (3) Ion reactions

(1) 1986HET/JAC (2) 1987TEW/FRE (3) 1995SCH/SCH

O30 O56 O56

O126 O234 O234

PD

1987HUA/BUC

(1) O66 (2) O87G5

O276 O364G21

(1) FT-MS (2) FT-MS

(1) 1984JAC/FRE(c) (2) 1985JAC/FRE(d)

–i-C4H8

FeLaC–C4H8 FeLaC–C4H6 FeRhC–C4H6

FeC(h5-C5H5)x–C5H5 xZ0

48G5 !56 43.4G1.0 39.1G0.5

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(3) 88G7 (4) 93.2

368G29 390

(5) 99.2G6.9 (4) 106.3 (5) 85.3G6.9

415G29 444.8 357G29

FeC–C5H6

(1) 55G5 (2) 51 (3) 50G5

FeRhC–C5H6

Methods (reference in parentheses)

References

(3) PD (4) Multiphoto ionization (5) TRPD

(5) 1995LIN/DUN

230G21 213G21 209G21

(1) PD (2) FT-MS (3) KERD

(1) 1986HET/JAC (2) 1988BUC/FRE (3) 1990DEA/BEA

O67

O280

PD

1987HUA/BUC

FeLaC–cyclo-C5H6 FeRhC–cyclo-C5H6

O50 O50

O209 O209

PD

1987HUA/BUC

FeC–(CH3)2 CHCHCH3

!56

!234

FT-MS

1987TEW/FRE

FeC–C6H4

(1) (2) (1) (3) (4)

O276 318G42 O268 297G21 293G21

(1) Ion reactions (2) PD

(1) 1978DIE/CHA (2) 1989HUA/FRE

(3) PD (4) KERD

(3) 1996FRE (4) 1990DEA/BEA

243G21

(1) Ion reactions

(1) 1984JAC/FRE(b)

1

–C6H5 –C6H8

FeC(C6H6)x–C6H6 xZ0

O66 76G10 O64 71G5 70G5

(1) 58G5

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

(3) 1990HUN/FRE (4) 1992OPI/HAR

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

(2) (3) (4) (5) (4) (5)

1

55G5 48.6G2.0 49.6G2.3 47 44.7G3.8 58

230G21 203. 3G8.4 207.5G9.6 197 187G16 243

(2) (3) (4) (5)

825

PD Ion reactions CID FT-ICR

(2) (3) (4) (5)

1986HET/JAC 1995SCH/SCH 1995MEY/KHA 2002GAP/DUN

(Cl)FeC(C6H6)x–C6H6 xZ0 1

64 !30

268 !126

FT-ICR

2002GAP/DUN

(Br)FeC(C6H6)x–C6H6 xZ0 1

65 !30

272 !126

FT-ICR

2002GAP/DUN

(I)FeC(C6H6)x–C6H6 xZ0 1

61 !30

255 !126

FT-ICR

2002GAP/DUN

FeRhC–C6H6

49–60

205–251

PD

1987HUA/BUC

FeLaC–C6H6 –CH3C6H5

R49.3 R48.9

R207 R204

Derived

1988HUA/FRE

FeC–phenyl –s-benzyl

(1) (1) (2) (1) (2) (1) (2)

297G21 264G21 230G21 347G42 R251G21 %540G21 O305

(1) PD

1996XU/GAR

217G10

Kinetics

–tolyl –cycloheptatrienyl

Fe+

(

YZp-CH3

Y

71G5 63G5 R55G5 83G10 R60G5 %129G5 O73

(2) Ion reactions

)

51.8G2.4

1998SCH/WES (continued)

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826

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment) p-C2H5 1,2-dimethyl 1,3-dimethyl 1,4-dimethyl 1,3,5-trimethyl 1,2,4-trimethyl 1,2,4,5-tetramethyl Pentamethyl Hexamethyl

Fe+

(

Y

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

52.9G2.4 53.9G2.5 53.6G2.5 53.8G2.5 55.2G2.6 55.2G2.6 56.6G2.7 57.8G2.7 58.9G2.8

221G10 226G10 224G10 225G10 231G11 231G11 237G11 242G11 246G12

(1) (2) (3) (1) (1) (1) (1) (1) (1)

209G10 251G25 O239 189G11 200G10 226G12 200G10 198G10 200G10

(1) Kinetics (2) Combined (3) Derived

(1) 1998SCH/WES (2) 1999RYZ/DUN (3) 2002DUN

)

YZOH

F CN NH2 1-F-2-methyl 1-F-3-methyl 1-F-4-methyl

50.0G2.5 60G6 O57 45.1G2.7 47.8G2.5 54.0G2.9 47.8G2.5 47.4G2.5 47.8G2.5

FeC–(cyclohepta -1,3,5-trine)

O56

O234

FT-MS

1987TEW/FRE

FeC–C10H8 (tetrlin) –C10H10 (1,2dihydro-naphth.) –C10H12 (naphthalene)

53.1 52.2

222.2 218.4

FT-ICR

1995SEE/HER

51.2

214.2

FeC–indole

O48

O201

Combined

1999RYZ/DUN

FeC–C60

44G7

184G29

Ion reactions

1995KAN/BYU

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds FeC–O

(1) (2) (3) (4) (5)

FeC(Fe)–O

344.3G5.8 %346.4 344.8 339G6 343.3G1.9

(1) (2) (3) (4) (5)

(1) O119 (2) 117.6

O498 492

(1) FT-MS (2) Review

(1) 1986JAC/FRE(b) (2) 2001ARM

129.1 136.0 131.5 126.9 120.0 129.1 131.5 133.8 138.4 142.9 136.0 149.9 140.8 140.8 133.8

540 569 550 531 502 540 550 560 579 598 569 627 589 589 560

Review

2001ARM

(1) 90G14 (2) 66

377G59 276

Ion beam

(1) 1982ARM/HAL (2) 1994SCH/FIE

FeCoC 2 ðOÞx –O xZ1 2 3

O85 O85 !25

O356 O356 !105

FT-MS

1986JAC/FRE(b)

RhFeC–O

O85

O356

PD

1987HUA/BUC

FeC–2O

O185G7

O774G29

FT-MS

1986JAC/FRE(b)

FeC(Fe)x–O xZ2 3 4 5 6 7 8 9 10 11 12 13 14 15 16

FeC(O)–O

82.3G1.4 %82.8 82.4 81.0G1.4 82.1G0.5

827

GIB MS PD Review Review UV PI

(1) (2) (3) (4) (5)

1989LOH/FIS 1999HUS/AGU 2001ARM 2003ARM 2005MET/NIC

(continued)

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828

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment) FeC(Fe)–2O

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 221G17 (2) 216.8

925G71 907

(1) FT-MS (2) Review

(1) 1986JAC/FRE(b) (2) 2001ARM

FeC x –2O xZ3 4 5 6 7 8 9 10 11 12 13 14 15 16

258.4 274.4 274.4 276.8 258.4 262.9 267.4 265.3 256.0 251.4 253.6 260.5 246.7 230.6

1081 1148 1148 1158 1081 1100 1119 1110 1071 1052 1061 1090 1032 965

Review

2001ARM

FeC(Co)–2O

221G17

925G71

FT-MS

1986JAC/FRE(b)

FeC–OH

(1) (1) (2) (3) (4) (5)

73G3 77G6 85.3G3 87.5G7 87.5G2.9 86.0G2.3

305G13 322G25 357G13 366G29 366G12 360G10

(1) (1) (2) (3) (4) (5)

PD PT CID Knudsen cell Review Evaluation

(1) 1984CAS/FRE (2) (3) (4) (5)

1989MAG/DAV(b) 1990GOR/MIL 1996ARM/KIC 2003SCH/SCH

(1) (2) (3) (4) (5) (1)

36.6G1.8 31.8G3 31.2G0.2 30.9G0.9 32.6 37.1G3.4

153G8 133G12.6 130.5G0.8 129.3G3.9 137 155G14

(1) (2) (3) (4) (5)

CID KERD Ion reactions Re-evaluated FT-ICR

(1) (2) (3) (4) (5)

1991SCH/CRE 1995CAR/KOP 1995SCH/SCH 1997TJE/ARM 2003CAE/HEN

FeC(CO)x–CO xZ0

1

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

2

3

4

(4) (6) (1) (4) (6) (1) (4) (6) (1) (4) (6)

35.3G1.2 41.5G1.6 15.9G1.2 16.4G1.4 25.7G1.4 24.7G1.4 23.3G1.4 25.2G1.1 26.8G0.9 23.2G0.9 17.8G0.9

147.8G4.8 173.6G6.7 67G5 68.5G5.7 107.5G5.9 103G6 97.4G5.7 105.4G4.6 112.1G4 97.1G3.9 74.5G3.8

829

(6) PEPICO

(6) 1990NOR/ALI

FeC(H)(CO)4–CO

30.1

126

MS

1993EKE/HAG

FeCD–CO

12.7G3.0

53G13

GIB MS

1995TJE/ARM

FeC(H2O)–CO

36.6

153.3

FT-ICR

2003CAE/HEN

FeC(CH3)–CO

8.3G3.2

35G14

GIB MS

1996TJE/ARM

(1) (2) (3) (4) (5) (5) (5) (5) (5)

33.4G8 39.7G8 54.4G5.4 59.8G3.9 74.3G7.7 121.6G8.7 36.7G7.7 89.7G12.5 68.5G5.8

(1) (2) (3) (4) (5)

(1) (2) (4) (4) (5)

w14.3

w60

Est. by exp.

2004KOS/SCH(b)

(1) (2) (3) (4) (5)

137.2 131.8G5.0 128.9G0.8 128.0G5.0 135.1G19.3

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

FeC(CO2)x–CO2 xZ0

1 2 3 4

(CH3O)FeC–CO2

FeC(H2O)x–H2O xZ0

8G2 9.5G2 13.0G1.3 14.3G0.9 17.8G1.8 29.1G2.1 8.8G1.8 21.4G3.0 16.4G1.4

32.8 31.5G1.2 30.8G0.2 30.6G1.2 32.3G4.6

Ion reactions Ion reactions Equilibrium CID CID

CID CID FT-ICR CID CID

1994STO/SCH 1995SCH/HEI 1997DIE/HAR 2001TJE/WAL 2005ARM/KOI

1989MAR/SQU 1994DAL/HON 1995SCH/SCH 1996ARM/KIC 2001POI/PRA (continued)

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

830

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment) 1

2 3

BDEs (boldfaceZ recommended data; reference in parentheses)

(1) (2) (4) (6) (2) (4) (2) (4)

kcal/mol

kJ/mol

40.8 39.3G1.0 39.3G1.0 38.0 18.3G0.9 18.2G0.9 11.8G1.6 19.6G1.2

170.7 164.4G4.2 164.4G4.2 159.0 76.6G3.8 76.1G3.8 49.4G6.7 82.0G5.0

Methods (reference in parentheses)

References

(6) CID

(6) 1989MAG/DAV(b)

FeC(D)–H2O

32.7G3.2

137G14

GIB MS

1995TJE/ARM

FeC(CH3)–H2O

21.4G3.0

90G13

GIB MS

1996TJE/ARM

HeminC(H2O)x–H2O heminZFe(III) protoporphyrin xZ0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

24.9G4.1 32.6G5.9 38.4G7.1 42.1G8.4 44.5G7.5 45.9G8.0 47.3G6.1 49.3G4.8 50.6G4.7 51.1G4.4 50.8G3.7 49.9G3.5 48.4G3.1 48.1G2.4 46.0G1.0 w44

(1) ESI

(1) 2005NON/IWA

(2) Extrapolate

(2) This volume

HeminCHis(H2O)x– H2O, heminCHisZ heminC-histidine xZ0

(1) 5.9G1.1

24.8G4.5

(1) ESI

(1) 2005NON/IWA

5.9G1.0 7.8G1.4 9.2G1.7 10.1G2.0 10.6G1.8 11.0G1.9 11.3G1.5 11.8G1.2 12.0G1.1 12.2G1.1 12.1G0.9 11.9G0.8 11.6G0.7 11.5G0.6 11.0G0.2 w10.5

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

1 2 3 4 5 6 7 8 9 10 11 12 13 14 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

7.1G1.5 8.4G1.9 9.3G2.2 9.6G2.0 10.3G2.1 10.5G1.6 10.6G1.3 10.8G1.2 11.2G1.2 11.4G1.0 11.4G0.9 11.4G0.8 11.0G0.6 10.9G0.3 w10.5

831

29.9G6.5 35.1G7.8 39.0G9.3 40.2G8.2 43.2G8.8 43.9G6.7 44.4G5.3 45.2G5.2 46.9G4.9 47.9G4.1 47.7G3.8 47.9G3.4 46.2G2.6 45.5G1.1 w44

(2) Extrapolate

(2) This volume

[(EDTA)Fe(OH)] –H2O2

1.6G0.1

6.8G0.4

Review

2005KRY/AKI

FeC–furan

48

201

FI-ICR

2004GRI/MAN

485G43 455G14 510G16 527G25 451G22 558G25 425G26 494G25 383G32 471G27 417G30 473G29 400G28 487G31 501G33 529G43 535G48 462G46 541G42 456G47 500G49 451G42

Ion reactions

(1) 2003LIY/GRI

FeC(Fe)x–N xZ1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16

(1) (1) (1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (2) (2) (2) (2) (2) (2) (2) (2)

116.0G10.4 108.8G3.5 122.0G3.9 125.9G6 107.7G5.3 133.3G6 101.5G6.2 118.1G6 91.5G7.6 112.5G6.5 99.6G7.1 113.0G6.9 95.7G6.7 116.5G7.4 119.7G7.8 126.4G10.4 128.0G11.5 110.5G11.0 129.4G10.1 109.1G11.3 119.5G11.8 107.7G10.1

(2) 2006TAN/LIU

(continued)

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

832

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment) 17 18

FeC(N2)x–N2 xZ0

1 2 3 4

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

(2) 117.4G5.5 (2) 106.1G3.2

491G23 444G14

(1) (2) (3) (4) (4) (4) (4) (4)

44G8 54G6 56G5 53G4 83G9 45G6 54G4 62G4

(1) (2) (3) (4)

10.5G2 12.9G1.4 13.4G1.1 12.7G0.9 19.8G2.1 10.8G1.4 12.9G0.9 14.8G0.9

Ion reactions CID Equilibrium CID, revised

References

(1) (2) (3) (4)

1995SCH/HEI 1997TJE/ARM 1997DIE/HAR 2001TJE/WAL

FeC(Fe)x–ND xZ1 2 3 4 5 6 7 8 9 10 11

78.9 108.8 126.8 107.9 97.3 95.0 99.2 101.0 104 111.1 98.0

330 455 531 452 407 398 415 423 434 465 410

Ion reactions

2003LIY/GRI

FeC–NO

34–58

142–243

Ion reactions

1985CAS/FRE

FeC–NCH –NH

(1) (2) (2) (3) (4) (4) (5) (6)

163G8 226G59 255G21 289G8 266.3G8.7 277.9G11.6 280G50 309G10

(1) (2) (2) (3) (4)

Ion reactions Ion reactions PD Ion reactions GIB MS

(1) 1994STO/SCH (2) 1988BUC/GOR

(5) Ion reactions (6) Re-evaluated

(5) 1988BUC/FRE (6) 1996ARM/KIC

–NH2

39G2 54G14 61G5 69G2 63.6G2.1 66.4G2.8 67G12 73.9G2.3

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

(3) 1998BRO/KRE (4) 2005LIY/ARM

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds FeC(Fe)x–ND2 xZ0 1 2 3 4 5 6 7

833

66.9–69.6 52.8 62.3 66.0–67.8 61.3 76.3 74.3 74

280–291 221 261 276–284 257 319 311 310

Ion reactions

2003LIY/GRI

(1) (2) (1) (2) (2) (2)

161 184G12 204 227G11 69G15 44G7

CID

(1) 1989MAR/SQU (2) 1998WAL/ARM

49.8 31.8–43.3 46.1–48.8 22.9–38.7 54.9 34.8 39.9 42.2

208 133–181 193–204 96–162 230 146 167 177

Ion reactions

2003LIY/GRI

FeC–pyridine

(1) (2) (3) (4)

205.0G12.6 225.0G8.9 206.7G10 209.2

(1) (2) (3) (4)

(1) (2) (3) (4)

FeC–pyrimidine

47.8G1.9

199.8G7.8

CID

2001AMU/ROD

HeminC(pyridine)x –pyridine heminZFe(III) protopor phyrin xZ0

(1) 24.6G0.1

102.9G0.5

(1) ESI

(1) 2005NON/IWA

FeC(NH3)x–NH3 xZ0 1 2 3

FeC(Fe)x–ND3 xZ0 1 2 3 4 5 7 8

38.5 44.0G2.9 48.7 54.3G2.9 16.5G3.6 10.5G1.7

49G3 53.8G2.1 49.4G2.4 50

Kinetics CID Kinetics Derived

1996MA/WON 2000ROD/STA 2001SCH/SCH(b) 2003DIE/TRA

(continued)

7366—CHAPTER 18—6/2/2007—13:21—JEBA—15374—XML MODEL B – pp. 803–853

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Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment) 1 2 3 N

FeC(pyrrole)x–pyrrole xZ0

BDEs (boldfaceZ recommended data; reference in parentheses)

(1) (1) (1) (2)

kcal/mol

kJ/mol

Methods (reference in parentheses)

13.3G0.8 9.0G0.5 8.8G0.1 w8.4

55.6G3.2 37.8G2.0 36.9G0.5 w35

(2) Extrapolate

(2) This volume

References

(1) 48G5 (2) 54.1 (2) 41.5

201G21 226 173.6

(1) CID (2) Kinetics

(1) 1996BAK/JAC (2) 2000GAP/YAN

FeC–quinoxaline FeC–2,3 -didehydropyrazine

47G5 87G10

197G21 364G42

FT-ICR

1999CHE/JAC

FeC–OSiH3

72G4

301G17

FT-ICR

1999BRO/SCH

(1) (2) (3) (2) (2) (2)

139.7G0.8 138.0G6.8 142G8 172.7G7.7 102.3G4.8 80.1G5.8

(1) Ion reactions (2) CID (3) CID

(1) 1995SCH/SCH (2) 1997TJE/ARM (3) 1997CHE/CHE

35.7G0.3 41.4G0.7

149.4G1.3 173.2G2.9

Ion reactions

1995SCH/SCH

(1) (2) (3) (3) (4)

272G25 297G4 295.2G5.8 346G12 258.6G37.6

(1) PD (2) CID (3) CID

(1) 1989MAC/JAC (2) 1996HAR/HEI (3) 1999SCH/KRE

(4) Derived

(4) 2003KRE/SCH

1

FeC(CH2O)x–CH2O xZ0

1 2 3

FeC–CH3CHO –C3H6O

FeC(S)x–S xZ0

1 2

33.4G0.2 33.0G1.6 34G2 41.3G1.8 24.4G1.2 19.1G1.4

65G6 71.0G0.9 70.6G1.4 82.8G2.8 61.8G9

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds FeC n ðSÞx –S, nZ3–6; xZ0–4

R74

R308

FeC(Fe)x–S xZ1 2 3 4

97.3G1.2 113.9G2.8 122.0G3.9 124.8G9

407.2G4.8 CID 476.6G11.6 510.4G16.4 522G38

2002KOS/SCH(b)

SFeC(Fe)x–S xZ1 2

103.8G5.5 127.5G8.1

434.2G23 533.6G34

CID

2002KOS/SCH(b)

FeC–SH –SD

66.0G2.6 66.0G2.6

276G11 276G11

CID

1999BAR/KRE

(1) (2) (1) (1) (1) (1)

201G21 223G12 205G21 205G21 180G21 159G21

(1) PD (2) CID

(1) 1989MAC/JAC (2) 1999SCH/KRE

(1) 55.3G2.8 (2) 49.5G3.1

231.6G11.6 207G13

CID

(1) 1999SCH/KRE (2) 2000ROD/ARM(b)

FeC(CS2)x–CS2 xZ0 1

39.7G1.1 45.0G1.4

166.1G4.6 188.3G5.9

Ion reactions

1996CAP/FEN

FeC–CH2S

37w50

155w209

CID

1997CHE/CHE

FeC–C4H4S –C4H5N

48G5 48G5

201G21 201G21

Ion reactions

1996BAK/JAC

FeC(S)x–S2 xZ0 1 2 3 4

FeC–CS

48G5 53.3G2.8 49G5 49G5 43G5 38G5

Derived

835

2004KOS/SCH(c)

(continued)

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

836

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds

The broken bonds (boldfaceZdissociated fragment) –C4H6

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

48G5

201G21

FeC(c-C5H5)–C4H4O –C4H4S

O46G5 O46G5

O193G21 O193G21

Ion reactions

1996BAK/JAC

FeC–CH3CN

41.3G0.7

172.8G2.9

Ion reactions

1995SCH/SCH

11.4 9.1 O9

47.7 38.1 O38

HP MS

(h5-C5H5)2FeHC –CH3CN

12.9

54.0

HP MS

1989MEO

(CO)5HFeC–CH3CN

16.8

70.3

HP MS

1991ALL/CRA

HeminC(Me2SO)x –Me2SO xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

115.8G24.1 77.2G14.5 61.7G9.6 57.9G9.6 54.0G9.6 w43

(1) ESI

(1) 2002NON/TAN

(2) Extrapolate

(2) This volume

O34 51.0

HP MS

1989MEO

(h5-C5H5)2FeC –CH3CN –2CH3CN –(CH3)2O

(h5-C5H5)2FeC–L LZC6H6 N,N-dimethyl-4toluidine

27.7G5.8 18.4G3.5 14.8G2.3 13.8G2.3 12.9G2.3 w10.3

O8 12.2

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

1989MEO

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds (h5-C5H5)2Fe

837

12

50

FeC–adenine

62.9G2.2

263G9

FeC–imidazole

58.8G3.3

246.1G13.8 CID

2004RAN/AMU

FeC–Si –SiH –SiH2

(1) (1) (1) (2) (1)

277G9 254G13 181G9 230–331 183G9

(1) GIB MS

(1) 1995KIC/ARM(b)

(2) FT-MS

(2) 1993JAC/BAK

–SiH3

66.2G2.1 60.6G3 43.3G2.1 55–79 43.8G2.1

GIB MS

2002ROD/ARM

FeC–Si(CH3)H –CH2SiH2 –Si(CH3)2 –CH2Si(CH3)H –CH2Si(CH3)2

56–78 55–70 60–77 55–71 55–73

234–326 230–293 251–322 230–297 230–305

FT-MS

1993JAC/BAK

FeC 2 –H

52G16

218G67

CID

1987FOR/LEC

FeC 2 ðClÞx –Cl xZ0 1 2 3 4 5

111 93 56 55 62 15

464 389 234 230 259 63

Derived

2001SCH/LOO

FeC 2 ðCOÞx –CO xZ0 1 2 3 4 5 6 7 8

24.2G2.1 28.4G2.4 29.7G2.1 28.8G2.1 18.7G1.8 25.4G1.8 18.9G2.5 7.6G1.8 24.9G2.5

101.3G8.7 CID 118.7G9.6 124.5G8.7 120.6G8.7 78.2G7.7 106.1G7.7 79.1G10.6 31.8G7.7 104.2G10.6

2000MAR/SUG

Fe2C(C6H6)x–C6H6 xZ0

116.2G7.4

486.3G30.9 CS MS

2001SCH/SCH(b) (continued)

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

838

Comprehensive Handbook of Chemical Bond Energies

Table 18.1.2 (continued) BDEs of FeC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

1

63.2G7.8

264.4G32.8

Fe2C–O

118.8G1.2

497G5

GIB MS

1989LOH/LIA

Fe2C–OH

58G12

243G50

FAB

1993MCC/LEB

Fe2C–O2

118.8G3.5

497G14

GIB MS

1989LOH/LIA

Fe2C(bpy)(CH3OH)x –(CH3OH) bpyZtris(2,2 0 bipyridyl) xZ1 2 3 4 5 N

(1) (1) (1) (1) (1) (2)

49.8 49.5 44.6 42.3 39.1 w37

(1) PD

(1) 1997SPE/BUR

(2) Extrapolate

(2) This volume

Fe3C–O

O119.2G0.2

O498.8G 0.8

GIB MS

1989LOH/LIA

11.9 11.8 10.7 10.1 9.3 w8.7

18.1.3 FeK–X bonds Table 18.1.3 BDEs of Fe––X Bonds

The broken bonds (boldfaceZdissociated fragment) FeK–Fe

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol (1) 44.7G2.1 (2) 37.8 (3) 42.1G0.2

kJ/mol 187.0G8.7 158.1 176.1G1.0

Methods (reference in parentheses) (1) CID (2) Derived (3) Derived from EA in ref.

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

References (1) 1988LOH/LIA (2) 1996SMI/YAT (3) 1996NIST

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

FeK(H)x–H xZ0

839

(1) 47.3G3 (2) 56.2G4.1 (2) O75

197.9G12.6 235G17 O314

Derived

(1) 1985SAL/LAN (2) 1991ARM/SUN

FeK(CO)4–H

70G14

293G59

Review

1991MIL/BEA

(CO)4FeK–Cl

(1) O72.9 (2) 70.3 (1) O69.2 (2) 70.6 (1) O53.6 (2) 55.0

O305 294 O290 295.4 O224 230.1

(1) PES (2) Kinetics

(1) 1984MCD/SCH (2) 1989JON/MCD

132

552

MS

1996HAR/HEI

(1) 33.7G3.5 (2) 33.3G8.1 (1) 35.7G3.5 (1) 42.4G3.5 (1) 41.7G2.5

141.0G14.6 139G34 149.4G14.6 177.4G14.6 174.5G10.5

(1) CID (2) PES

(1) 1992SUN/SQU (2) 1993VIL/LEO

(h5-C5H5)FeK(CO)–CO

44.9G3.8

188G16

CID

1999SUN/SQU

FeK(CO)4–CHO

(1) 44.7G8.6 (2) w41

187G36 w172

Review

(1) 1990SIM/BEA (2) 2004DAM

FeK–S FeK–SH

O103 83G9

O431 347G38

Derived

1989SAL/LAN

1

–Br –I

FeK–O

FeK(CO)x–CO xZ0 1 2 3

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

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Comprehensive Handbook of Chemical Bond Energies

18.2 Ru– and RuC–X bonds 18.2.1 Ru–X bonds Table 18.2.1 BDEs of Ru–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ru–Ru

(1) 74.5 (2) 46.1G4.6

312 193.0G19.3

(1) Correlation (2) Raman

(1) 1986MOR (2) 1997WAN/LIU

Ru(100, surf.)–Li

10.6 (phys)

44.4

NMR

1996EBI/JAN

Ru(100, surf.)–Li

73.7

308.3

NMR

1998EBI/ARN

Ru(100, surf.)–K

(1) 19.8G1.2 (phys) (2) 9.0G0.4

83G5

(1) LEED

(1) 1985WEI/UMB

37.7G1.7

(2) LITD

(2) 1993WES/BRO

Ru(100, surf.)–K

42

176

Review

1995SEE/ALL

Ru(1000, surf.)–Cs

71.5

299.1

TPD

1996PAY/MCK

Ru–Ce

118.0G2.9

494G12

MS

1989CHA/GIN

Ru–Th

141.4G10

592G42

MS

1974GIN

Ru–V

98.9G6.9

414G29

Review

1986MOR

Ru(1000, surf.)O–Cu

20.8

86.8

STM

1999WOL/MEI

Ru(100, surf.)–Ag

57.4G1.2

240G5

TDS

1987NIE/DOL

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

841

Ru(100, surf.)–Au

93.2G1.2

390G5

TDS

1987NIE/DOL

Ru(1000, surf.)–Kr

3.5

14.7

TDS

1992SCH/MEN

Ru(1000, surf.)–Xe

(1) 5.3 (2) 14.8G0.7

22.2 61.7G2.9

(1) TDS (2) Photoemmis.

(1) 1992SCH/MEN (2) 2000BER/HOF

Ru–H

(1) 56G5 (2) 53.3G3.5

234G21 223G15

Ion reactions

(1) 1986TOL/BEA (2) 1999ARM/CHE

Ru(100, surf.)–H

(1) 4.0G0.5 (phys) (2) 3.6G0.5

16.7G2.1

LITD

(1) 1986MAK/BRA

15.1G2.1

(2) 1987MAK/BRA

Ru(100, surf.)–D

4.1G0.5 (phys) 17.2G2.1

LITD

1987MAK/BRA

Ru(100, surf.)–H

(1) 67 (2) 29.5

280 123.4

TDS

(1) 1985FEU/MEN (2) 1995JAC/MEN

Ru(1000, surf.)–H

66.0

276

Review

1998CHR

Ru(1010, surf.)–H

61.2

256

Adsorption

1989LAU/SCH

(CO)2(h5-C5H5)Ru–H

64.9

271.5

Electrochemical

1991PAR/HAN

(PMe3)2(h5 -C5Me5)Ru–H

40.0

167.4

Review

1992DRA/WON

96.1 110.9 81.0 86.3

402 464 339 361

MS

1988HIL/LAU

Ru(F)x–F xZ0 1 2 3

(continued)

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

842

Comprehensive Handbook of Chemical Bond Energies

Table 18.2.1 (continued) BDEs of Ru–X Bonds

The broken bonds (boldfaceZdissociated fragment) (CO)2(h5-C5Me5) Ru–Cl –Br

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

80.7 61.1

337.6 255.6

55.6

232.6

!33 !36

!138 !151

!36

!151

Ru–O

126G10

Ru(100, surf.)–O

Methods (reference in parentheses)

References

Derived

1995LUO/LI

Kinetics

1989BRY/DOM

528G42

Review

1990SIM/BEA

99.5

416

Review

1991BEN

Ru(101, surf.)–O

95.4

399

Ru(1000, surf.)–O

104

435

TPS

1988KEL/GEL

Ru(1000, surf.)–N

21.7 (phys)

90.7

STM

1996ZAM/TRO

Ru–C

155G3

648G13

Review

1990SIM/BEA

124

519

Ru–Si

94.9G5

397G21

MS

1970MAH/PEE

Ru–B

106.8G5

447G21

MS

1970MAH/PEE

–I

(h5-C5Me5) (PMe3)2Ru–Cl –Br –I

–C2

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

Ru(dmpe)2–H2 dmpeZ1,2bis(dimethyl) phos-phinoethane

63.5G2.0

Ru(100, surf.)–H2 –D2

PAC

1993BEL/SCA

3.6G0.5 (phys) 15.0G2.1 4.1G0.5 17.2G2.1

LITD

1987MAK/BRA

Ru(100, surf.)–H2

30

126

TPD

1985FEU/MEN

Ru(1120, surf.)–H2 Ru(1010, surf.)–H2

(1) 17.5 (2) 19.1

73 80

(1) Review (2) LEED

(1) 1978MAD/BEN (2) 1989LAU/SCH

Ru–O2

74.1G1

310G4

Torsion-effusion

2004BRU/SCA

Ru(surf.)–O2

52.6

220

Review

1982RAO/KAM

(1) !29 (2) 48.9 (1) !33 (2) 21.5 (2) 63.0

!121 204.6 !138 90.0 263.6

(1) Kinetics (2) Review

(1) 1989BRY/DOM (2) 1992DRA/WON

(CO)4Ru–CO

27.5G0.4

115G1.7

Kinetics

1980HUQ/POE

Ru(C2H2)(CO)4–CO

24.9G0.6

104G2.4

Kinetics

1998PEA/COO

Ru(PPh3)(CO)3–CO

30.1

125.9

Kinetics

1980HUQ/POE

Ru(dmpe)2–CO dmpeZ1,2bis(dimethyl) phosphinoethane

43.0G2.0

179.9G8.4

PAC

1993BEL/SCA

(h5-C5Me5) (PMe3)2Ru–OH –SH –CN

265.7G8.4

843

(continued)

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

844

Comprehensive Handbook of Chemical Bond Energies

Table 18.2.1 (continued) BDEs of Ru–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ru(100, surf.)–CO

11 (phys)

46

LITD

1989DEC/BRA

Ru(100, surf.)–CO

(1) (2) (3) (4) (5)

160G4 150 142.3 159 125.5

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Ru(1010, surf.)–CO

(1) 31.2 (2) 28

130.5 117

Review

(1) 1978MAD/BEN (2) 1991BEN

Ru(1120, surf.)–CO

29

121

Review

1978MAD/BEN

Ru(1011, surf.)–CO

28

117

Review

1978MAD/BEN

Ru(1120, surf.)–CO

21.3–24.6

89–103

TDS

2001WAN/WAN

Ru(001, surf.)K–CO

18.4

77.2

TDS

1985PAO/HRB

Ru(1000, surf.)Cu–CO

17.1

71.4

Mol. beam

1999KNE/GEM

Ru(dmpe)2–N2 dmpeZ1,2 -bis(dimethyl) phos-phinoethane

18.8G2.0

78.7G8.4

PAC

1993BEL/SCA

Ru(100, surf.)–N2

8 (phys)

33

LEED

1983ANT/AVE

38.2G1.4 35.9 34 38 30

TPD TPD TPD FT-IRAS FT-IRAS

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

1983PFN/FEU 1989LAU/SOL 1990BRA/ARE(b) 1991HOF/WEI 1991PED/GOO

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

Ru(1000, surf.)–N2

845

(1) 44.0G0.5 (2) 45.4 (3) 34.7 (step site)

184.1G2.1 190 145

(1) Kinetics (2) TDS (3) TPD

(1) 1987TSA/WEI (2) 1995SHI/JAC (3) 2000DAH/TOR

Ru(1010, surf.)–N2 Ru(1121, surf.)–N2 Ru(1120, surf.)–N2

(1) 28.6G2.4 (2) 27.5 (3) 28.6G4.8

120G10 115 120G20

TDS

(1) 1997DIE/JAC (2) 2001JAC/WAN (3) 2004WAN/JAC

Ru(100, surf.)–NH3

21.4

89.5

TDS

1983BEN/MAD

(1) !40 (2) 34.0 (2) 29.0

!167 142.3 121.3

(1) Kinetics (2) Review

(1) 1989BRY/DOM (2) 1992DRA/WON

RuO2(110, surf.) –H2CO

24

100.4

Re-anal.

2001MAD/IDR

RuO2(100, surf.)–C2H4

11.6G1

48.5G4

HR-EELS

1986HIL/PAR

Ru(oep)(C2H5)–C2H5 oepZ2,3,7,8,12,13,17, 18-octaethylpor phyrinato anion

21.7G1.5

90.8G6.3

Kinetics

1986COL/WHI

(h5-C5Me5)(PMe3)2 Ru–OCH3

33.9

141.8

Review

1992DRA/WON

Ru(100, 2!2, surf.)–HCOH

w16

w67

TDS

1986ANT/PAR

(h5-C5Me5) (PMe3)2Ru–L LZCH2COCH3

(1) !36 (2) 28.7

!151 120

(1) Kinetics (2) Review

(1) 1989BRY/DOM (2) 1992DRA/WON

Ru(1000, surf.)–N2

(h5-C5Me5) (PMe3)2Ru–CH3 –C2H5

(continued)

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

846

Comprehensive Handbook of Chemical Bond Energies

Table 18.2.1 (continued) BDEs of Ru–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ru(100, surf.) –(CH3)2CO

16

67

Review

1988SHU

Ru(100, surf.) –(C2F5)2O

8.8–9.3

37–39

TDS

1990LEA/THI

Ru(100, surf.)–C3H8

3 (phys)

13

LITD

1990BRA/ARE

Ru(100, surf.)–C3H8

11.0G0.5

46.0G2.1

LITD

1990BRA/ARE

Ru(100, surf.)–nC4H10

3.5 (phys)

15

LITD

1990BRA/ARE

Ru(100, surf.)–nC4H10

11.9G0.5

49.8G2.1

LITD

1990BRA/ARE

Ru(100, surf.)–nC5H12

4.5 (phys)

19

LITD

1990ARE/DEC

Ru(100, surf.)–nC5H12

13.8G0.9

57.7G3.8

LITD

1990ARE/DEC

Ru(100, surf.) –iso-C5H12

4.1 (phys)

17

LITD

1990ARE/DEC

Ru(100, surf.) –iso-C5H12

13.5G0.4

56.5G1.7

LITD

1990ARE/DEC

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

847

Ru(100, surf.) –cyclo-C5H12

3.3 (phys)

14

LITD

1990ARE/DEC

Ru(100, surf.) –cyclo-C5H12

11.9G0.5

49.8G2.1

LITD

1990ARE/DEC

Ru(100, surf.) –neo-C5H12

3 (phys)

13

LITD

1990ARE/DEC

Ru(100, surf.) –neo-C5H12

10.7G0.2

44.8G0.8

LITD

1990ARE/DEC

Ru(100, surf.)–nC6H14

4.8 (phys)

20

LITD

1990BRA/ARE

Ru(100, surf.)–nC6H14

15.0G0.5

62.8G2.1

LITD

1990BRA/ARE

Ru(100, surf.)–C4F10

13.8G0.6

57.7G2.5

LITD

1991ARE/WES

Ru(100, surf.) –((CH3)2SiH)2

12.3G0.5

51.5G2.1

LITD

1990WES/ARE

(h5-C5Me5)(PMe3)2 Ru–L LZCH2Si(CH3)3

(1) !34 (2) 31.0

!142 129.7

(1) Kinetics (2) Review

(1) 1989BRY/DOM (2) 1992DRA/WON

(h5-C5H5)(CO)2 Ru–CH2C6H5

33

138

Thermolysis

1992MAN/HAL

(h5-C5Me5)(PMe3)2 Ru–C6H5 –CH2C6H5 –CCC6H5

(1) (2) (1) (1) (2)

!155 167.4 !159 !176 264.8

(1) Kinetics (2) Review

(1) 1989BRY/DOM (2) 1992DRA/WON

!37 40.0 !38 !42 63.3

(continued)

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

848

Comprehensive Handbook of Chemical Bond Energies

Table 18.2.1 (continued) BDEs of Ru–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(h5-C5Me5)(PMe3)2 Ru–OC6H5 –SC6H5

!33 !32

!138 !134

Kinetics

1989BRY/DOM

(h5-C5Me5)(PMe3)2 Ru–L LZNH(C6H5) N(C6H5)2

!28 !23

!117 !96

Kinetics

1989BRY/DOM

16.8 12.1

70.3 50.6

Combined

2003HIL/SOM

LZ4-Me-phenyl Mesityl 2,6-Diiso propylphenyl

18.8 15.6 11.1

78.7 65.3 46.4

Combined

2003HIL/SOM

(h5-C5Me5)Rn(Cl) –PCy3 PCy3ZP(cyclohexyl)3

10.5

43.9

Combined

2003HIL/SOM

(h5-C5H5)(CO)2 Ru–U(h5-C5H5)3

40.4G4

169G17

Review

1994NOL

R

N

N

R

LZmesityl 2,6-Diiso propylphenyl

(h5-C5Me5)Rn(Cl)–L R N

N

R

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

849

18.2.2 RuC–X bonds Table 18.2.2 BDEs of RuD–X Bonds BDEs The broken bonds (boldfaceZdissociated fragment) RuC–H

(h5-C5H5)2RuC–H

(boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 41G3

172G13

(2) 38.3G1.2

160.2G5.0

Methods (reference in parentheses) Ion reactions

References (1) 1984MAN/HAL (2) 1995CHE/ELK

(1) 79G5

331G21

(1) Thermochem.

(1) 1981STE/BEA

(2) 64.8G3.6

271G15

(2) Review

(2) 1990SIM/BEA

(3) 69.8G3.8

292G16

(3) Re-evaluated

(3) 1992RIC

(1) 67.9

284.1

Electrochemical

(1) 1995PED/SKA

(h5-C5H5)(PMe3)I

(2) 68.0 (2) 66.8

284.5 279.5

(h5-C5H5)(dppm)H

(2) 70.7

295.8

(2) 69.4

290.4

(2) 68.3

285.8

108.4G2.5 119.9G2.8

453.5G10.6 501.7G11.6

82.3G1.2

344.4G4.8

(1) 54G5

226G21

(1) Ion reactions

(1) 1984MAN/HAL

(2) 38.3G1.4

160.2G5.8

(2) Ion reactions

(2) 1999ARM/CHE

(3) O42.1

O176

(3) Review

(3) 1990SIM/BEA

RuC–C2H2

(1) 45.7G4.2

191.0G17.3

(1) Ion reactions

(1) 1999ARM/CHE

–CCH2

(1) 78.2G4.4

327.1G18.3

–C2H3

(1) 69.9G1.6

292.3G6.8

–C2H4

(1) O30.9G0.2

O129.3G1.0

(2) 30

125.5

(2) Review

(2) 1998SCH/SCH

(1) 73.6G3.5

307.8G14.5

(L)RuC–H LZ(h5-C5Me5)2

(2) 1996WAN/ANG

dppm: Ph2PCH2PPh2 (h5-C5H5)(dppe)H dppe: Ph2P(CH2)2PPh2 (h5-C5H5)(PPh3)2H

RuC–C –CH –CH2

Ion reactions

1999ARM/CHE

RuC(CH3)x–CH3 xZ0 1

–CHCH3

(continued)

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

850

Comprehensive Handbook of Chemical Bond Energies

Table 18.2.2 (continued) BDEs of RuC–X Bonds BDEs (boldfaceZrecommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

–C2H5

RuC–C3H4

kJ/mol

(1) 28w44

117w183

51.7G2.8

216.1G11.6

–C3H6

O28.1G0.2

O117.7G1

–C4H6

O54.9G0.2

O229.6G1

–C4H8

O23.1G0.2

O96.7G1

RuC(O)x–O xZ0

Methods (reference in parentheses)

Ion reactions

References

1999ARM/CHE

(1) 88.9G1.2

372G5

(1) Ion reactions

(1) 1995CHE/ARM(c)

(2) 79

331

(2) Derived

(2) 2000SCH/SCH

RuC–S

68.8G1.4

288G6

Ion reactions

2003ARM

RuC–CS

60.5G4.8

253G20

CID

2000ROD/ARM(b)

65.0

272.0

Electrochemical

2002ROU/NAT

72.6

303.8

1

Cp'

Cp'

H Ru

OC

Ru

OC

CO L

Cp 0 Zh5-C5Me5 LZCO h5-C5H5

CO

C5H4CH2

CO

70.8

296.2

Tp Fv

CO CO

67.8 74.5

283.7 311.7

C5H4CH2C5H CO

74.8

313.0

Ind

CO

69.1

289.1

h5-C5H5

PMe3

73.1

305.9

Tp: hydrotris (pyrazolyl)borate Fv: C10H8 Ind:h5-C9H7

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

(h5-indenyl)RuC(L)2–L

16.6G2.3

69.5G10

(h5-indenyl)RuC(L)–2L

34.6G2.3

145G10

15.2G0.9

63.6G3.8

17.3G0.8

72.4G3.3

xZ0

17.6G0.8

73.6G3.3

1 2

15.4G0.7 16.8G0.8

64.4G2.9 70.3G3.3

3

16.2G1.0

67.8G4.2

851

FT-ICR

2002WES/ROS

ESI-FT-ICR

2002STE/DUN

ESI-FT-ICR

2002STE/DUN

BIRD

2004STE/DUN

LZPHPh2

Ru2C(bipy)3–CH3COCH3 –CH3CN

Ru2C(bipy)3Lx–L LZCH3C(O)C2H5

Ru2C(NH3)2(bipy)2Lx–L LZCH3C(O)CH3 xZ0

19G1

79.5G4

1

19G1

79.5G4

5

19G1

79.5G4

18.3 Os– and OsC–X bonds 18.3.1 Os–X bonds Table 18.3.1 BDEs of Os–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Os–Os

99G18

415G77

Correlation

1986MOR

Os–Ce

125.2G4.8

524G20

MS

1989CHA/GIN

Os(H)(CO)4–H

78

326.4

Electrochemical

1991EIS/LAW

(h5-C5H5)(CO)2Os–H

82

343.1

AOP

2005ZHA/GRI (continued)

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

852

Comprehensive Handbook of Chemical Bond Energies

Table 18.3.1 (continued) BDEs of Os–X Bonds

The broken bonds (boldfaceZdissociated fragment) Os(C)x–C xZ0

1

Os(O)x–O xZ0 1 2 3

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 155G3 (2) 145.3G6

649G13 608G25

(1) 136 (2) 132G5.5

569 553G23

(1) (1) (1) (1) (2)

137.4 129.5 136.2 104.0 78.3G14.4

Methods (reference in parentheses)

References

(1) Review (2) Derived from DfH0 in ref.

(1) 1990SIM/BEA (2) 2001MEL/THO

575 542 570 435 328G60

(1) MS

(1) 1992HIL/LAU(b)

(2) Derived

(2) 1989IRI/BEA

Os(surf.)–O2

47

196

Review

1982RAO/KAM

Os(0001, surf.)–CO

35.7

150

TPD

1983VEN/SCH

(CO)4Os–CO

(1) 30.6G0.3 (2) 31.8G0.6

128G1.3 133G2.6

Kinetics

(1) 1989SHE/GAO (2) 1998PEA/COO

Os(C2H2)(CO)4–CO Os(PPh3)(CO)3–CO

23.8G0.2 40.2G0.7

99.5G0.8 168G2.9

Kinetics

1998PEA/COO

OsO4–HC OsOC 4 –H

161G2 132G3

674G8 552G13

Derived

1989IRI/BEA

OsO3–OHC

101G16

423G67

Derived

1989IRI/BEA

7366—CHAPTER 18—6/2/2007—13:22—JEBA—15374—XML MODEL B – pp. 803–853

BDEs of Fe(FeG)–, Ru(RuC)–, and Os(OsC)–X Bonds

853

18.3.2 OsC–X bonds Table 18.3.2 BDEs of OsD–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

OsC–H

57.1

238.9

Review

1990OHA/GOD

OsO4–HC OsOC 4 –H

161G2 132G3

674G8 552G13

Derived

1989IRI/BEA

298 300 264.4 277.8 273.2 295.0 307.9

Electrochemical

(1) 1995PED/SKA (2) 1996WAN/ANG

(L)OsC–H LZ(C5Me5)2

(1) (2) (2) (C5H5)(PPh3)2Br (C5H5)(PPh3)2Cl (2) (C5H5)(PPh2Me)2Br (2) (2) (C5H5)(PPh3)2Br (2) (C5H5)(PPh3)2H

71.2 71.7 63.2 66.4 65.3 70.5 73.6

OsC–CH2

O111

O464.4

ICR

1991IRI/BEA

OsC–C2H4

45

188.3

Review

1998SCH/SCH

OsC(O)x–O xZ0 1 2 3

100G12 105G12 105G12 71G12

418G50 441G50 441G50 299G50

FT-ICR

1989IRI/BEA

7366—CHAPTER 18—6/2/2007—13:23—JEBA—15374—XML MODEL B – pp. 803–853

chapter nineteen

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X bonds 19.1 Co–, CoC– and CoK–X bonds 19.1.1 Co–X bonds Table 19.1.1 BDEs of Co–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) Co–Co

recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 21.6

90.6

(2) %30.4

%127

Methods (reference in parentheses) Review

References (1) 1996SMI/YAT (2) 2001ARM

Co(Co)x–Co xZ1

(1) R33.4

R140

2

(1) 55.6

233

3

(1) 65.5

274

4 5

(1) 76.3 (1) 61.1

319 256

6

(1) 67.6

283

7

(1) 66.6

279

8

(1) 70.3

294

9

(1) 71.9

301

10

(1) 78.6

329

11

(1) 84.9

355

12 13

(1) 71.9 (1) 88.6

301 371

14

(1) 88.1

369

15

(1) 79.3

332

16

(1) 88.6

371

(1) Review

(1) 2001ARM

(continued)

855

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

856

Comprehensive Handbook of Chemical Bond Energies

Table 19.1.1 (continued) BDEs of Co–X Bonds

The broken bonds (boldfaceZdissociated fragment) N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 101.7

425

(2) Review

(2) 1994ARM/HAL

(3) w90

w377

(3) Extrapolate

(3) This volume

(1) 11.5G4.6

48.1G19.2

(1) MS

(1) 1967BID/MCI

(2) 20.6

86.2

(2) Derived

(2) 1975GAR/CAR

(3) 15.3

64.0

(3) Review

(3) 1994NOL

(4) 19G2 (5) 19.8G6.9

79.5G8 83G29

(4) NMR (5) Derived

(4) 1994KLI/RAT (5) 1995GOE/AHY

(CO)4Co–Mn(CO)5 –Re(CO)5

22.9G2.9 27.0G3.6

96G12 113G15

Derived

1992CON

Co–Y

60.64G0.02

253.71G0.10

Spectrometry

1994ARR/BLU

Co–Nb

63.82G0.02

267.02G0.10

Spectrometry

1994ARR/BLU

Co–Ti

56.26G0.02

235.37G0.10

Spectrometry

1992SPA/MOR(b)

Co–Zr

73.23G0.02

306.39G0.10

Spectrometry

1994ARR/BLU

Co–Mn

12.0G1.9

50.0G8

CID

1991HOP/MCM(b)

(CO)4Co–Co(CO)4

Co–Cu

(1) 38.0G5

159.0G20.9

(1) MS

(1) 1970KAN/STR

(2) 38.5G3.9

161.1G16.4

(2) Review

(2) 1986MOR

Co–Au

52.1G3.9

218.0G16.4

Review

1986MOR

Co–Al

43.4G0.1

181.6G0.2

Spectrometry

2001FU/RUS

Co–H

(1) 45.1G1

188.7G4

(1) MS

(1) 1981KAN/MOO

(2) 54G3

226G42

(2) Ion reactions

(2) 1986TOL/BEA

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

857

(3) 46.6G3.2

194.9G13.5

(3) CID

(3) 1991FIS/ARM

(4) 44.0G1.2

184G5

(4) Review

(4) 1996ARM/KIC

(5) 58.5G1.2

244.9G4.8

(5) Spectroscopy

(5) 2002PRI/GOM

Co–D

64.6G1.4

270.2G5.8

Spectroscopy

2000PRI/GOM

Co(CO)4–H

(1) 66.4

277.8

(1) Electrochemical

(1) 1991PAR/HAN

(2) 56

234

(2) Derived

(2) 1991KRI/NOR

(3) 58

242.7

(3) Review

(3) 1994NOL

(4) 59G1

246.9G4

(4) NMR

(4) 1994KLI/RAT

(5) 66.4

278

(5) Review

(5) 2001TIL

(1) 65.2

272.8

(1) Electrochemical

(1) 1991PAR/HAN

(2) 65.2

273

(2) Review

(2) 2001TIL

(1) 65.0

272.0

(2) 65.0

272

Co(polycs. surf.)–H

64

268

Review

1979TOY/SOM

Co(0001, surf.)–H

w16 (phys)

w67

TPD

1979BRI/COM

Co(0001, surf.)–H

59.8

250

Review

1988CHR

Co(1010, surf.)–H

(1) 60.0

251

(1) Review

(1) 1988CHR

(2) 61.7

258

(2) TPD

(2) 1994ERN/SCH

103G15 78G10

431G63 326G42

Review

1974GUR/KAR

67G5

280G21

(Co(CO)3)(L)–H LZP(OPh)3 PPh3

Co–F –Br –I

Co(Cl)x–Cl xZ0 1

(1) 80.7G1.6

337.6G6.7

(1) MS

(1) 1995HIL

(2) 97.5

407.9

(2) Derived from

(2) 1996NIST

DfH0 in ref.

(continued)

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

858

Comprehensive Handbook of Chemical Bond Energies

Table 19.1.1 (continued) BDEs of Co–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

Methods

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

(reference in

kJ/mol

parentheses)

References

2

(2) 45.7

191.2

3

(2) 73.7

308.4

(pyridine)Co(DH)2–I DH2Zdimethylglyoxime

34.6G1.4

144.8G5.9

Co–O

(1) 87.3

365.2

(1) MS

(1) 1966GRI/BUR

(2) 91.9G3.2

384.5G13.4

(2) Spectroscopy

(2) 1989MER

Kinetics

1989TOS/SEL

(3) 57.7G2.3

241.2G9.6

(3) CID

(3) 1990FIS/ARM

(4) 95.0G2.1

397.4G8.7

(4) CID

(4) 2005LIU/LI

Co–S

79

331

Review

1972SMO/MAN

Co–Si

65.6G4.1

274.4G17

MS

1969MAH/MCL

Co–Ge

(1) 56G6

234G25

(1) MS

(1) 1968KAN/STR

(2) 55G5

230G21

(2) Review

(2) 1974GUR/KAR

24.1

100.8

Calorimetry

1975AND

Co(polyc. surf.)–H2

Co(polyc. surf.)–O2

(1) 102

426

(1) Calorimetry

(1) 1960BRE/HAY

(2) 100

418

(2) Calorimetry

(2) 1965BRE/HAY

(3) 98

410

(3) Calorimetry

(3) 1966BRE/GRA

(4) 114

478

(4) Review

(4) 1982RAO/KAM

(5) 109.9G6

460G25

(5) Adsorption

(5) 1988OST

CoO(polycr. surf.)–O2

65

272

Review

1964HAY/TRA

Co(polycr. surf.)–CO

18–20 (phys)

75–84

IR

1967KAV/SOK

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

859

Co(polycr. surf.)–CO

47

197

Calorimetry

1965BRE/HAY

Co(0001, surf.)–CO

(1) 24.6G1 (2) 28

103G8 117

(1) TPD (2) Review

(1) 1977BRI/COM (2) 1991ZHD

(3) 30.6

128

(3) LEED

(3) 1983PAP

(4) 27.4

114.5

(4) TDS

(4) 1998LAH/KAU

Co2–CO

36.9

154.4

Combined

2002TRE/MAN

CoO(polycr. surf.)–CO

20

84

Review

1964HAY/TRA

(CO)3HCo–CO

w13

w54

Kinetics

1969UNG/MAR

(h5-C5H5)Co(CO)–CO

44.0G1.2

184.3G4.8

UV PES

2003SZT/SZE

Cob(II)alamin–NO

18.2G0.2

76G1

UV/VIS spectra

2001WOL/ZAH

YZH p-Cl

23.4 22.8

97.9 95.4

Calorimetry

2002ZHU/LI

m-Cl

23.4

97.9

p-Br

23.3

97.5

m-Br

22.8

95.4

p-Me

24.1

100.8

m-Me

23.5

98.3

p-i-Pr

24.2

101.3

p-OMe m-OMe

24.6 23.3

102.9 97.5

p-NO2

21.1

88.3

m-NO2

20.8

87.0

Co(II)–NO bonds Y

N Y

N

NO

N

Co II

Y

N

Y

(continued)

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

860

Comprehensive Handbook of Chemical Bond Energies

Table 19.1.1 (continued) BDEs of Co–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Co(III)–NO bonds Y

Y

N

NO N Co II

N

N

Y

Y

YZH

16.8

70.3

p-Cl

16.7

69.9

m-Cl

16.8

70.3

p-Br

16.7

69.9

m-Br

16.3

68.2

p-Me

17.2

72.0

m-Me

16.6

69.5

p-i-Pr p-OMe

16.9 17.5

70.7 73.2

m-OMe

16.8

70.3

p-NO2

15.2

63.6

m-NO2

15.1

63.2

Co(polycr. surf.)–CO2

Calorimetry

2002ZHU/LI

(1) 35

146

(1) Review

(1) 1964HAY/TRA

(2) 37

155

(2) Calorimetry

(2) 1965BRE/HAY

CoO(polycr. surf.)–CO2

23

96

Review

1964HAY/TRA

CoO(polycr. surf.)–ON2

13 (phys)

54

Review

1964HAY/TRA

CoO(polycr. surf.)–ON2

50

209

Review

1964HAY/TRA

Co–CH2

79G9

331G38

Proton affinity

1989JAC/GOR

Co–CH3

(1) 46G3 (2) 42.5G2

192.5G13 178G8

(1) GIB MS (2) Review

(1) 1989GEO/FIS (2) 1996ARM/KIC

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

(pyridine)Co(DH)2–CH3

861

33.1G1.6

138.5G6.7

Kinetics

1989TOS/SEL

(1) 1992MAR/FIN

(DH)2Zdimethylglyoxime

Me–Cbl (i.e., CH3–cobalamin)

(1) 37G3

154.8

(1) Thermolysis

(2) 36

150.6

(2) PAC

(2) 1999HUN/GRA

(3) 31G2

129.7G8.4

(3) Electrochemical

(3) 2006BIR/HUA

Me–Cb1 (base-on)

39G5

163G21

TR PAC

1998LUO/LI

Me–Cb1 (base-off)

R42G5.5

R176G23

CH3–cobinamide (i.e., Me–Cbi)

37

154.8

PAC

1999HUN/GRA

PAC

2002LI/ZHA

Kinetics

2005GAL/KUB

Kinetics

1998FUK/MIY

(L)(salen)Co–CH3 LZH2O

40.2G2

168G8

Imidazole

36.3G2

152G8

Benzimidazole

32.5G2

136G8

Pyridine

30.4G2

127G8

CH3–CoPc(py)

30G1

125.5G4.2

C2H5–CoPc(py)

29G1

121.3G4.2

(TPP)Co–CH3

!19.7

!82

–C2H5

!19.8

!83

–C4H9

!19.3

!81

CoO(polycr. surf.)–C2H4

13

54

Review

1964HAY/TRA

(H2O)(salen)Co–C2H5 salen

29.9G2

125G8

PAC

2002LI/ZHA

salenZ bis(salicylidene)ethylenediamine

PcZdianion of phthalocyanine pyZpyridine

TPPZtetraphenylporphyrin dianion

Zbis(salicylidene)ethylenediamine

(continued)

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862

Comprehensive Handbook of Chemical Bond Energies

Table 19.1.1 (continued) BDEs of Co–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment) (py)(saloph)Co–CH2CH2CH3

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

25

104.6

Kinetics

1982TSO/LOO

cobinamide–CH(CH3)2

26.3

110

Kinetics

1990SIM/BEA

(py)Co(DH)2–CH(CH3)2

21.3G2.4

89.1G10.0

Kinetics

1989TOS/SEL

20

83.7

Kinetics

1982TSO/LOO

19.4G2

81G8

PAC

2002LI/ZHA

!19.5G0.9

!81.6G3.8

Kinetics

1998WOS/WAY

(1) 18G1 (2) 17.8G0.6

75.3G4 74.5G2.5

Equilibrium

(1) 1994WAY/GRI (2) 1996WOS/XIE

(salen)(H2O)Co–nC4H9

(1) 27.7G2 (2) 25.6G2

116G8 107G8

PAC

(1) 2000ZHA/LI (2) 2002LI/ZHA

(salen)Co–nC4H9

Kinetics

1991WOL/BAL

pyZpyridine

pyZpyridine, (DH)2Zdimethylglyoxime

(py)(saloph)Co–CH(CH3)2 pyZpyridine

(H2O)(salen)Co–CH(CH3)2 salenZ bis(salicylidene)ethylenediamine

(TPP)Co–C(CH3)2CN TPPZtetraphenylporphyrin dianion

(TAP)Co–C(CH3)2CN TAPZtetraanisylporphyrinato

24.4G0.5

102.1G2.2

salenZ

24.5G0.3

102.3G1.3

bis(salicylidene)ethylene-

27.8G0.6

116.2G2.4

diamine

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

863

L(salen)Co–nC4H9 LZpyridine

34.6G0.6

144.9G2.7

PCy3 salenZbis(salicylidene)-

28.7G0.4

120.0G1.6

Kinetics

1991WOL/BAL

(H2O)(salen)Co–iC4H9

21.5G2

90G8

PAC

2002LI/ZHA

Cobinamide–iC4H9

24.9

104

Kinetics

1990SIM/BEA

EI

2003OPI

1982TSO/LOO

ethylene-diamine CyZtricyclohexylphosphine

Co(h5-C5H5)x–(h5-C5H5) xZ0

63.9

267.3

1

81.6

341.5

18

75.3

Kinetics

(1) 23.7

99

Kinetics

(2) 28G2

117G8

(1) 3.2

13.4

(1) Calorimetry

(2) 3.6

15.2

(2) Solubility

(1) 3.7

15.3

(1) 8.1 (2) 7.9

34 33.1

(1) 6.1

25.5

(2) 6.5

27

7.8

32.8

39.4

165.0

(py)(saloph)Co–CH2C(CH3)3 pyZpyridine

Cobinamide–CH2C(CH3)3

Co(tmhd)2–cyclo-C6H12 –C6H6

(1) 1990SIM/BEA (2) 1993WAD/FIN

1996CHA/EMM

tmhdZ2,2,6,6-tetramethyl-3,5heptanedionate

Co(tmhd)2bpy–cycloC6H12 –C6H6

(1) Calorimetry (2) Solubility

1996CHA/EMM

Derived

2001PAN/RAO

tmhdZ2,2,6,6-tetramethyl-3,5heptanedionate bpyZbipyridine

Co(C6H6)x–C6H6 xZ0 1

(continued)

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

864

Comprehensive Handbook of Chemical Bond Energies

Table 19.1.1 (continued) BDEs of Co–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Co(Cl)2(py)x–pyridine xZ0

37.2

155.5

1

18.2

76.0

Derived

1997EMM/PIC

LZMe

8.2

34.5

Et

5.2

21.9

Thermal analysis

1988MOR/STE

n-Pr

3.2

13.3

i-Pr

2.4

10.0

n-Bu

2.0

8.4

t-Bu

3.2

13.3

Co(tmhd)2–bipy

23.2G1.2

97G5

Thermochemical

1996CHA/EMM

Co(L)(I)–CH2C(CH3)3

30.4

127

Kinetics

1990SIM/BEA

36.3

152

LZC(aCH2)(CH2)2CH3

30.9

129.3

Equilibrium

1996WOS/XIE

cyclo-C5H9 TAPZtetraanisylporphyrinato

30.9

129.3

Cobinamid–CH2–cyclo-C5H9

23.7

99

Kinetics

1990SIM/BEA

22.7

95

(L)Co(salen)–pyridine

salenZ bis(salicylidene)ethylenediamine

–CH2C6H5 LZC2(DO)(DOH)pnZ11hydroxy-2,10-diethyl-3,9dimethyl-1,4,8,11-tetraazaundeca-1,3,8,10-tetra-1olato

(TAP)Co–L

–CH2C6H5

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

(py)(saloph)Co–CH2C6H5

865

22

92.0

Kinetics

1982TSO/LOO

24G3

100G13

Kinetics

1984BAK/ESP

Kinetics

1991WOL/BAL

pyZpyridine

Co(dmgBF2)2(H2O)–CH2C6H5 dmgBF2Zdimethylglyoxime BF2

L(Hdmg)2Co–CH2C6H2 LZPMe3

31.8G0.7

133.2G2.8

PEt3

26.0G0.2

108.9G0.8

PBu3

30.2G1.3

126.4G6.5

PPh3 PCy3

22.8G0.1 27.1G0.3

95.5G0.6 113.4G1.3

pyridine

26.0G0.6

108.7G2.7

4-CN–pyridine

33.9G1.0

142.0G4.1

24G3

100G13

Kinetics

1987BAK/ESP

Kinetics

1987GEN/HAL

HdmgZdimethylglyoxime PCy3Ztricyclohexylphosphine

Co2C([14]aneN4)(H2O)– CH2C6H5, [14]aneN4Z 1,4,8,11-tetra-aza-cyclotetradecane

Co(L)(OEP)–CH2C6H5 LZP(n-Bu)3

29.3

122.6

P(c-C6H11)3

29.6

123.8

PMe2Ph

27.1

113.4

PEtPh2

26.1

109.2

23.7

99.2

PPh3 OEPZoctaethyporphyrinate dianion

Co(L)(dimethylglyoxime)2– CH2Ph LZP(n-Bu)3

(1) 21

87.9

(1) Kinetics

(1) 1983NG/REM

(2) 28.9

120.9

(2) Kinetics

(2) 1987GEN/HAL

(3) 20.8 (2) 22.8

87.0 95.4

(3) Review

(3) 1994NOL

P(c-C6H11)3 PMe2Ph

(1) 24

100.4

(2) 30.4

127.2

(3) 23.9

100.0

(continued)

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

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Comprehensive Handbook of Chemical Bond Energies

Table 19.1.1 (continued) BDEs of Co–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

(1) 19

79.5

(2) 26.8

112.1

PEtPh2

(1) 19

79.5

PPh3

(1) 17 (2) 25.8

71.1 107.9

(3) 17.4

72.8

pyridine

(3) 27.0G2.0

113.0G8.4

(DH)2Zdimethylglyoxime

(4) 31.2G2.2

130.5G9.2

(4) Kinetics

(TAP)Co–CHMeC6H5

(1) 19.5G0.6

81.6G2.5

Equilibrium

TAPZtetraanisylporphyrinato

(2) !22.5G0.5

94.1G2

PhMeCH–Co(py)(DH)2

PEtPh2

(1) 19.7

82.4

–(4-NH2–py)Co(DH)2

(1) 21.2

88.7

–(2-NH2–py)Co(DH)2

(2) 16.6

69.5

–(4-CH3–py)Co(DH)2

(1) 20.1

84.1

–(4-CN–py)Co(DH)2

(1) 17.9

74.9

(2) 16.9

70.7

pyZpyridine

References

(4) 1989TOS/SEL

(1) 1996WOS/XIE (2) 1998WOS/WAY

Kinetics

(1) 1982NG/REM (2) 1990NG/REM

(DH)2Zdimethylglyoxime

PhMeCH–L (1) 20.8

87.0

Co(P(CH2CH2CN)3)(DH)2

(2) 20

83.7

(2) 1983NG/REM

Co(CH3COCH3)(DH)2

(3) 16.9

70.7

(3) 1990NG/REM

!18.2G0.5

!76.1G2.1

Kinetics

1998WOS/WAY

Kinetics

1990SIM/BEA

LZCo(imidazole)(DH)2

Kinetics

(1) 1982NG/REM

(DH)2Zdimethylglyoxime

(TAP)Co–CC(CH3)2COOCH3 TAPZtetraanisylporphyrinato

CH(CH3)COOCH3–L LZ(py)Co(DH)2

28.7

120

(4-CH3–py)Co(DH)2

29.4

123

(4-CN–py)Co(DH)2

28.2

118

pyZpyridine

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

(pyridine)Co(DH)2–

867

33.2

139

Kinetics

1990SIM/BEA

Co–C bond in 3,4,-anAdoCb1

24G2

100.4G8.4

Thermolysis

2000MAG/FRE

–CH(CH2COOCH3)COOCH3

Co–C bonds

(1) 26G2

108.8G8.4

(1) Kinetics

(1) 1984HAL/KIM

B12–Ado

(2) 30G2

125.5G8.4

(2) Kinetics

(2) 1986HAY/FIN

AdoZ5 0 -deoxyadenosyl

(3) 29.6G1.5

123.8G6.3

(3) Kinetics

(3) 1997CHE/YAN

B12Zcobinamide

(4) 31.3G2.9

131G12

(4) PAC

(4) 1998LI/LUO

Co–C bonds in AdoCbl AdoCblZ5 0 -

33.8G0.2

141.4G0.8

Kinetics

1999BRO/ZOU

34.8G0.3

145.6G1.3

Kinetics

2005BRO/ZOU

Co–C bonds

(1) 32.4G1.5

135.6G6.3

(1) Kinetics

(1) 1997CHE/YAN

B12–2 0 -dAdo; 2 0 dAdo: 2 0 ,5 0

(2) 31.8G2.5

133.1G10.5

(2) PAC

(2) 2003CHE/LI

Co–C bonds 5 0 -deoxy-5 0 -adenosylcobalamin

30.8G4.1

129G17

TR PAC

1998LUO/LI

(CO)4Co–SiMe3

Derived

1977BUR/STO

deoxyadenosylcobalamin

Co–C bonds in Ado(Im)Cbl Ado(Im)CblZCob-5 0 deoxyaenosylimidazolylcobamide

-dide-oxyadenosyl

O55.3G2.3

O231.6G9.6

–GeMe3

73.8G2.3

308.7G9.6

–SnMe3

64.6G2.3

270.2G9.6

(continued)

7366—CHAPTER 19—3/2/2007—11:18—BSARAVANAN—15375—XML MODEL B – pp. 855–902

868

Comprehensive Handbook of Chemical Bond Energies

Table 19.1.1 (continued) BDEs of Co–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

Methods

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

(reference in

kJ/mol

parentheses)

References

Co–Sn bonds CoIII(OEP)–SnR3 RZn-Bu

O30

O126

Ph OEPZoctaethyporphyrinate

O30

O126

Est. by exp.

1998CAO/PET

Kinetics

1997SIR/FIN

dianion

Co–Nax bond in MeCbi–NMeIm 8

33

ImZimidazole

19.1.2 CoC–X bonds Table 19.1.2 BDEs of CoD–X Bonds

The broken bonds (boldfaceZdissociated fragment) CoC–Co

CoC(Co)x–Co xZ1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

CID CID Review Review

References

(1) 63.4G2.3 (2) 63.8 (3) 64.3 (4) 64.3

265.3G9.6 266.9 269.0 269

(1) (2) (3) (4)

(1) 48.1 (2) 44.2 (2) 48.9 (2) 65.6 (2) 76.3 (2) 67.6 (2) 72.4 (2) 67.6 (2) 68.0 (2) 74.9 (2) 78.6 (2) 83.9 (2) 72.4 (2) 90.9 (2) 84.9 (2) 82.8 (2) 88.8 (3) 88.8

201.3 185 205 274 319 283 303 283 285 314 329 351 303 380 355 346 371 371

(1) CID (2) Review

(1) 1994RUS/HEI (2) 2001ARM

(3) CID

(3) 1994HAL/SU

7366—CHAPTER 19—3/2/2007—11:19—BSARAVANAN—15375—XML MODEL B – pp. 855–902

(1) 1990HAL/ARM (2) 1994RUS/HEI (3) 1996SMI/YAT (4) 2001ARM

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

N

869

(4) 101.7 (5) w90

425 w377

(4) Review (5) Extrapolate

(4) 1994ARM/HAL (5) This volume

CoC(O)–Co

O120G8

O502G34

FT-MS

1986JAC/FRE(b)

CoC–Fe

(1) 66G7 (2) 62G5 (3) 62G6

276G29 259G21 259G25

(1) FT-MS (2) PD (3) Ion reactions

(1) 1984JAC/FRE (2) 1987HET/FRE (3) 1987HET/FRE

CoC(O)–Fe

O117G8

O490G34

FT-MS

1986JAC/FRE(b)

(CO)4CoC–GeMe3 –SnMe3

32.3 25.4

135.1 106.1

Derived

1977BUR/STO

CoC(He)x–He xZ0 1 2

3.9G0.1 3.4G0.1 1.2G0.1

16.4G0.4 14.3G0.4 5.1G0.4

Equilibrium

1991KEM/HSU

CoC(Ne)x–Ne xZ0 1

2.18G0.1 1.95G0.1

9.2G0.4 8.2G0.4

Equilibrium

1991KEM/HSU

CoC–Ar

(1) 12.6 (2) 12.64G0.01 (3) 13.2

52.8 52.89G0.06 55.1

(1) PD (2) PD (3) GDMS

(1) 1989LES/BRU (2) 1994ASH/BEL (3) 1995BAR/SMI

CoC–Kr

(1) 16.3 (2) 16.34G0.04

68.3 68.37G0.18

PD

(1) 1989LES/BRU (2) 1995BUT/BEL(b)

CoC–Xe

(1) 22.9G0.4 (2) 20.5G1.6

95.8G1.8 85.7G6.8

(1) PD (2) CID

(1) 1995BUT/BEL(b) (2) 1995HAY/ARM

CoC–H

(1) !71 (2) 52G5 (3) 46.6G1.4

!297 218G21 195G6

Ion reactions

(1) 1979ALL/RID (2) 1985CAS/FRE (3) 1986ELK/ARM

(1) 47.3G1.4 (2) 47.7G1.4 (2) 54.2G2.1

197.9G5.8 199.6G5.8 226.7G8.7

GIB MS

(1) 1986ELK/ARM (2) 2005LIU/ARM

CoC(Co)x–D xZ0 1

(continued)

7366—CHAPTER 19—3/2/2007—11:19—BSARAVANAN—15375—XML MODEL B – pp. 855–902

870

Comprehensive Handbook of Chemical Bond Energies

Table 19.1.2 (continued) BDEs of CoC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) 2 3 4 5 6 7 8 9 10 11 12 13 14 15

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 45.9G2.5 (2) 51.9G3.7 (2) 49.6G5.3 (2) 52.3G6.7 (2) 50.0G6.7 (2) 50.5G7.1 (2) 54.4G7.6 (2) 57.0G8.1 (2) 57.0G8.3 (2) 58.3G8.5 (2) 61.1G8.1 (2) 61.6G8.1 (2) 61.6G8.1 (2) 62.0G8.5

192.0G10.6 217.1G15.4 207.4G22.2 219.0G28.0 209.4G28.0 211.3G29.9 227.7G31.8 238.3G33.8 238.3G34.7 244.1G35.7 255.7G33.8 257.6G33.8 257.6G33.8 259.5G35.7

CoC(H)–H

50

209

Review

1990SIM/BEA

CoC(O)–H

(1) 107G4 (2) 109

448G17 456

(1) Thermochemical (2) Est. by exp.

(1) 1986KAN/BEA (2) 1986CAS/FRE

CoC(C)–H CoC(CH)–H

91G10 84G5

381G42 351G21

Ion reactions

1986HET/FRE

(1) 73G5 (2) 58.6G2.9 (3) 35.3G1.8

305G21 245G12 147.6G7.7

(1) Thermochemical (2) Review (3) Ion reactions

(1) 1981STE/BEA (2) 1990SIM/BEA (3) 1994CHE/CLE

CoC(C2H4)–D

29.5G3.0

123.5G12.5

GIB MS

1996HAY/FIS(b)

CoC–Cl

(1) 70.2G2.8 (2) 68.1G2.8 (3) 57.2G5

294G12 285G12 239G21

(1) Ion reactions (2) Ion reactions (3) Derived from IP in ref.

(1) 1989FIS/SUN (2) 1996ARM/KIC (3) 1996NIST

CoC–Br

O69

O289

Ion reactions

1979ALL/RID

CoC–I

(1) O71 (2) 50.6G2

O297 211.7G8.4

Ion reactions

(1) 1979ALL/RID (2) 1993KOP/KEM

(L)CoC–H LZ(h5-C5H5)(CO)2 CH3OD

7366—CHAPTER 19—3/2/2007—11:19—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

CoC(H2)x–H2 xZ0

871

(1) 18.2G1.0 (2) 17.5G2.3 (1) 17.0G0.7 (1) 9.6G0.5 (1) 9.6G0.6 (1) 4.3G0.7 (1) 4.0G0.7

76.1G4.2 73G10 71.1G2.9 40.1G2.1 40.1G2.5 18.0G2.9 16.7G2.9

(1) Equilibrium (2) CID

(1) 1993KEM/BUS(b) (2) 1996HAY/ARM

CoC–D2

17.1G1.6

71.4G6.8

CID

1996HAY/ARM

(CH4)CoC–H2

17.4

72.8

Equilibrium

1999BOW/KEM

(H2O)CoC(H2)x–H2 xZ0 1 2

19.8 7.9 8.2

82.8 33.1 34.3

Equilibrium

1999BOW/KEM

(CO)CoC(H2)x–H2 xZ0 1 2

16.0 8.5 8.8

66.9 35.6 36.8

Equilibrium

1999BOW/KEM

(1) 15.6 (2) 16.2 (1) 17.1 (2) 16.8 (1) 1.1 (2) 0.9

65.3 67.8 71.5 70.3 4.6 3.8

Equilibrium

(1) 1999BOW/KEM (2) 2003CAR/KOP

(1) 90G7 (2) 83.9G6.9 (1) 100G7 (2) 100.3G8.8 (3) 85.3G6.9 (4) 85G7 (5) 77.5G1.6 (6) 75.8G1.2 (7) %79.1G0.5 (8) 50G6

377G29 351G29 418G29 420G37 357G29 356G29 324.2G6.8 317G5 %331G2 209G25

(1) PD (2) GIB MS

(1) 1986HET/FRE (2) 1995HAY/CHE

(3) Ion beam (4) FT-MS (5) GIB MS (6) Review (7) PD (8)FT-ICR

(3) 1981ARM/BEA (4) 1987FOR/LEC (5) 1990FIS/ARM (6) 1996ARM/KIC (7) 2000HUS/AGU (8) 1998CHE/AUB

78–93

326–389

PD

1987HUA/BUC

1 2 3 4 5

(h5-C5H5)CoC(H2)x–H2 xZ0 1 2

CoC–C –CH –CH2

–CF2

RhCoC–CH2

(continued)

7366—CHAPTER 19—3/2/2007—11:19—BSARAVANAN—15375—XML MODEL B – pp. 855–902

872

Comprehensive Handbook of Chemical Bond Energies

Table 19.1.2 (continued) BDEs of CoC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) FCoC–CF2

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

!30.9G1.4

!129.3G5.9

Ion reactions

1998CHE/FRE(b)

(1) 57G7 (2) 46G14 (3) 48.9G3 (4) 53.3G2 (5) 48.4G0.9 (6) 60.9G4.8

238G29 192G59 205G13 223G8.4 203G4 255G20

(1) (2) (3) (4) (5) (6)

(1) 1986HET/JAC (2) 1987FOR/LEC (3) 1989FIS/SUN (4) 1993KOP/KEM (5) 1996ARM/KIC (6) 1990SIM/BEA

(H)CoC–CH3

43.5

182

Review

1990SIM/BEA

(O)CoC–CH3

R53.5G1.2

R224G5

Ion reactions

1994CHE/CLE

(TPP)CoC–CH3 –C2H5 –C4H9 –C6H5 TPPZtetraphenylporphyrin dianion

!14.5 !8.7 !8.4 !15.0

!61 !36 !35 !63

Kinetics

1998FUK/MIY

(1) 49G11 (2) 22.9G0.7 (3) 21.4G1.4 (4) 23.1 (2) 24.8G0.8 (3) 23.1G1.2 (4) 25.3 (2) w11 (3) 9.5G1.2 (4) 7.3 (3) 15.5G1.4 (4) 5.2

205G46 96G3 89.5G6 96.7 104G3 96.7G5 105.9 w46 39.8G5 30.5 64.9G6 21.8

(1) (2) (3) (4)

(1) 1984JAC/FRE (2) 1993KEM/BUS (3) 1995HAY/ARM (4) 2001ZHA/KEM

17.2 9.2

72.0 38.5

Equilibrium

CoC(CH3)x–CH3 xZ0

1

CoC(CH4)x–CH4 xZ0

1

2

3

(CH3)CoC(CH4)x–CH4 xZ0 1

Ion reactions FT-MS GIB MS Kinetics Review Review

Ion reaction Equilibrium Ion reactions Equilibrium

7366—CHAPTER 19—3/2/2007—11:19—BSARAVANAN—15375—XML MODEL B – pp. 855–902

2001ZHA/KEM

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

873

(L)CoC–CH4 LZH2 H2O C2H6

22.6G1.2 25.9G0.8 24.0G1.2

95G5 108G3 100G5

Equilibrium

1993KEM/BUS

(h5-C5H5)CoC(CH4)x–CH4 xZ0 1 2

24.1 12.1 2.2

100.8 50.6 9.2

Equilibrium

2003CAR/KOP

(1) O39.9G4.6 (2) O8.3G3.5 (3) R6.5G3 (4) 43G2

O166.9G19.3 O34.7G14.5 R27.0G12.6 180G8

(1) (2) (3) (4)

GIB MS Revised GIB MS IRMPD

(1) 1990FIS/ARM (2) 1994FIS/ARM (2) 1994HAY/ARM (4) 1997SUR/RAN

(1) 37G2 (2) 42G5 (3) O40G4.6 (4) 42.9G1.6 (5) 44.5G2.2 (5) 36.3G3.3

155G8 176G21 O167G19 179.5G6.8 186G9 152G14

(1) (2) (3) (4) (5)

Ion reactions KERD GIB MS GIB MS GIB MS

(1) 1983JAC/FRE (2) 1990KOP/BOW (3) 1990FIS/ARM (4) 1996HAY/FIS(b) (5) 1998SIE/JAR

(1) 48.4G1.8 (2) 46.1G2.6 (3) O40.6G2.1 (4) 110G3 (5) 84.1

202.5G7.5 193G11 O170G9 460.2G12.6 351.9

(1) (2) (3) (4) (5)

GIB MS Review GIB MS KERD Ion reactions

(1) 199HAY/ARM (2) 1996ARM/KIC (3) 1996HAY/FIS (4) 1988HAN/BEA (5) 1992PER/GOD

26.1G3.7

109.0G15.4

GIB MS

1996HAY/FIS(b)

(1) 28.0G1.6 (2) 24.0G1.2 (1) 26.8G1 (1) !12

117.2G6.7 100.4G5.0 112G4 !50

(1) Equilibrium (2) GIB MS

(1) 1993KEM/BUS (2) 1996HAY/FIS(b)

(L)CoC–C2H6 LZCH4 (C2H6)2

28.4G1.3 !12

119G5 !50

Equilibrium

1993KEM/BUS

RhCoC–C2H6

O33

O138

PD

1987HUA/BUC

CoC–C3H3

(1) 89G17 (2) 83.0

372G71 347.3

(1) Ion reactions (2) EI

(1) 1985JAC/FRE (2) 2003OPI

CoC–C2H2

CoC(C2H4)x–C2H4 xZ0

1

CoC–C2H3 –C2H5 –(CH3)2

CoC(D)–C2H4

CoC(C2H6)x–C2H6 xZ0 1 2

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 19.1.2 (continued) BDEs of CoC–X Bonds

The broken bonds (boldfaceZdissociated fragment) –C3H4

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(3) O18.7G2.1 (4) 32.5G6 (3) 46.4G3.9 (3) 43.1G1.6 (5) 44G5 (6) 29.9G1.7 (7) 81G5 (8) 30.9G1.4

O78.2G8.7 136G25 194G16 180G7 184G21 125G7 339G21 129.3G5.8

(3) GIB MS (4) FT-ICR

(3) 1994HAY/ARM (4) 1997NAN/FRE

(5) (6) (7) (8)

(5) 1992BEA/KOP (6) 1996ARM/KIC (7) 1996FRE (8) 1996HAY/FIS

RhCoC–C3H8

O30

O126

PD

1987HUA/BUC

RhCoC–C3H4

O33

O138

PD

1987HUA/BUC

CoC–C4H6

(1) O85.9 (2) !52

O359 !218

Ion reactions

(1) 1984TSA/ALL (2) 1988BUC/FRE

CoC(h5-C5H5)–C4H6

O57

O238

Ion reactions

1988BUC/FRE

CoRhC–C5H6

O67

O280

PD

1987HUA/BUC

FeRhC–cyclo-C5H6

O50

O209

(1) O84 (2) O76G7 (3) 85G3 (4) 91.8 (5) 78.2G0.7 (3) 123G10 (4) 112.1

O351 O318G29 356G12 384.0 327.1G2.9 513G42 469

(1) (2) (3) (4) (5)

CoC(C5H8)x–C5H8 xZ0 1

85G5 118G10

356G21 494G42

Ion reactions

1985JAC/FRE

CoC(C6H6)x–C6H6 xZ0

(1) 68G5

285G21

(1) PD

(1) 1986HET/JAC

–C3H5 –C3H6 –C3H6(cyclo) –C3H6(metallocyclic) –C3H8

CoC(h5-C5H5)x–(h5-C5H5) xZ0

1

KERD GIB MS Review GIB MS

Ion reactions Ion reactions Review EI Derived

7366—CHAPTER 19—3/2/2007—11:20—BSARAVANAN—15375—XML MODEL B – pp. 855–902

(1) 1984JAC/FRE(c) (2) 1985JAC/FRE(d) (3) 1990SIM/BEA (4) 2003OPI (5) 2003SZT/SZE

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

875

(2) 61.1G2.6 (2) 39.9G3.3

256G11 167G14

(2) CID

(2) 2000ROD/ARM(b)

O49

O205

PD

1987HUA/BUC

63.4G2.6 64.2G2.6 65.2G2.7 65.2G2.7 65.3G2.7 66.8G2.8 66.9G2.8 68.2G2.9 69.7G2.9 70.9G3.0

265G11 269G11 273G11 273G11 273G11 279G12 280G12 285G12 292G12 297G13

Kinetics

1998SCH/WES

YZF Cl Br I OH NH2 CN 1-F-2-methyl 1-F-3-methyl 1-F-4-methyl 1-Cl-2-methyl 1-Cl-3-methyl 1-Cl-4-methyl

56.2G2.9 57.4G2.9 58.4G3.1 60.1G3.3 61.0G2.7 64.8G2.9 57.8G2.7 58.8G2.7 58.6G2.7 58.6G2.7 59.7G2.7 59.6G2.7 59.6G2.7

235G11 240G11 244G13 251G14 255G11 271G12 242G11 246G11 245G11 245G11 250G11 249G11 249G11

Kinetics

1998SCH/WES

CoC–cyclo-C7H8

O52G4

O218G17

Ion reactions

1986CAS/FRE

Co–C bond in AdoCbiC

34.5G1.8

144.3G7.5

Thermolysis

1990MAR/FIN

CoC–C60

58G16

243G67

Ion reactions

1994KAN/BYN

CoC–O

(1) 63.6G2.3 (2) 76.1G1.6

266.1G10 318.4G6.8

(1) Ion beam (2) GIB MS

(1) 1982ARM/HAL (2) 1990FIS/ELK

1

RhCoC–C6H6

Co+

(

Y

)

YZmethyl ethyl 1,2-dimethyl 1,3-dimethyl 1,4-dimethyl 1,3,5-trimethyl 1,2,4-trimethyl 1,2,4,5-tetramethyl pentamethyl hexamethyl

Co+

(

Y

)

(continued)

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876

Comprehensive Handbook of Chemical Bond Energies

Table 19.1.2 (continued) BDEs of CoC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(3) 76.0G1 (4) 71.4G5.7

318G4 299G24

(5) 75.8G1.2

317.3G4.8

(1) O119 (2) 102.8G1.4 (1) O85 (2) 105.2G3.7 (2) 114.6G4.4 (2) 107.9G5.8 (2) 105.8G5.1 (2) 110.0G6.0 (2) 106.1G4.4 (2) 108.2G4.4 (2) 110.0G6.9 (2) 113.2G7.4 (2) 112.5G8.1 (2) 104.5G8.8 (2) 115.5G9.7 (2) 104.5G9.7 (2) 101.9G10.6 (2) 109.1G13.6 (2) 113.9G11.5 (2) 112.5G11.5

CoC 3 ðOÞx –O xZ1 2 3

Methods (reference in parentheses)

References

(3) Re-evaluated (4) Derived from IP in ref. (5) Review

(5) 2005LIU/LI

O498 430.3G5.8 O356 440.0G15.4 479.5G18.3 451.5G24.1 442.9G21.2 460.2G25.1 443.8G18.3 452.5G18.3 460.2G28.9 473.7G30.9 470.8G33.8 437.1G36.7 483.4G40.5 437.1G40.5 426.5G44.4 456.4G56.9 476.6G48.2 470.8G48.2

(1) FT-MS (2) GIB MS

(1) 1986JAC/FRE(b) (2) 2005LIU/LI

O85 O85 !25

O356 O356 !105

FT-MS

1986JAC/FRE(b)

FeCoC 3 ðOÞx –O xZ1 2

O85 O85

O356 O356

FT-MS

1986JAC/FRE(b)

CoC(Fe)–O

O119

O498

FT-MS

1986JAC/FRE(b)

CoC 3 ðFeÞ–O

O85

O356

FT-MS

1986JAC/FRE(b)

CoC(Co)x–O xZ1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18

7366—CHAPTER 19—3/2/2007—11:20—BSARAVANAN—15375—XML MODEL B – pp. 855–902

(3) 1996ARM/KIC (4) 1996NIST

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

877

RhCoC–O

O85

O356

Photodissociation

1987HUA/BUC

CoC–2O

O185G7

O774G29

FT-MS

1986JAC/FRE(b)

CoC(Co)–2O

(1) 221G17 (2) 199.5G3.5

925G71 834.6G14.5

(1) FT-MS (2) GIB MS

(1) 1986JAC/FRE(b) (2) 2005LIU/LI

CoC(Co)x–2O xZ2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18

224.1G3.9 237.3G4.4 238.2G4.6 233.1G4.6 235.4G4.8 233.4G4.2 229.4G4.8 237.5G5.8 242.4G6.9 236.4G7.6 232.7G8.3 241.2G9.2 226.9G9.7 226.9G11.1 225.8G11.8 224.1G11.8 208.2G16.8

937.8G16.4 992.8G18.3 996.7G19.3 975.4G19.3 985.1G20.3 976.4G17.4 960.0G20.3 993.8G24.1 1014.0G28.9 989.0G31.8 973.5G34.7 100.9.2G38.6 949.4G40.5 949.4G46.3 944.6G49.2 937.8G49.2 871.2G70.4

GIB MS

2005LIU/LI

CoC(Fe)–2O

221G17

925G71

FT-MS

1986JAC/FRE(b)

Cob(II)esterC–O2

(1) 7.4G1.5 (2) 6G1 (3) 8.2G0.6

31.0G6.5 25.1G4.2 34.4G2.5

(1) ESR (2) EPR (3) EPR/ENDOR

(1) 1972ZEL (2) 1982JOR/SCH (3) 2001DOO/SCH

(1) 39G5 (2) 41.5G1.6 (3) 39.1G3 (2) 36.4G2.1 (2) 19.6G2.8 (2) 18.0G1.4 (2) 18.0G1.2

163G21 173.7G6.7 163.6G12.6 152.4G8.7 82.0G11.6 75.3G5.8 75.3G4.8

(1) KERD (2) CID (3) KERD

(1) 1988HAN/BEA (2) 1995GOE/HAY (3) 1995CAR/KOP

CoC(CO)x–CO xZ0

1 2 3 4

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 19.1.2 (continued) BDEs of CoC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) CoC(NO)(CO)x–CO xZ0 1 2

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

36.1G0.7 26.6G0.7 21.9G1.2

151.0G3 111.1G3 91.7G5

PES

2002SZT/BAE

(1) 35.3G0.5 (2) 29.7 (1) 34.6G0.5 (2) 32.3

147.6G2 124.5 144.7G2 135.1

(1) PES (2) EI

(1) 2000SZT/BAE (2) 2003OPI

(CoNOPCH3)C–CO (CoNOPC2H5)C–CO

18.7G1.6 18.0G1.7

78.2G6.8 75.3G6.8

TPEOICO

2005GEN/SZT

(CoCONOPCH3)C–CO (CoCONOPC2H5)C–CO

21.7G1.4 20.8G1.4

90.7G6.2 86.8G6.2

TPEOICO

2005GEN/SZT

CoC–OH

(1) 71G3 (2) 72G2 (3) 72.2G0.9 (4) 71.7G0.9 (5) 71.2G0.9

297G13 301G8 302G3.9 300G4 298G4

(1) (2) (3) (4) (5)

(1) 1984CAS/FRE(b) (2) 1989MAG/DAV (3) 1994CHE/CLE (4) 1996ARM/KIC (5) 2001FAH/THO

(1) 37–52 (2) 43.1G1.7 (2) 37.7G0.7 (2) 30.1G4.3

155–218 180.4G7 157.7G3 126.1G18

(1) Ion reactions (2) PES

(1) 1984CAS/FRE (2) 2002SZT/BAE

(CoPCH3)C–NO (CoPC2H5)C–NO

39.0G1.6 40.1G1.7

163.1G6.8 167.9G6.8

TPEOICO

2005GEN/SZT

CoC–CO2

19.9

83.3

PD

1994ASH/BEL(e)

(h5-C5H5)CoC(CO)x–CO xZ0 1

CoC(CO)x–NO xZ0 1 2

PD TQ MS GIB MS Re-evaluated Review

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BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

CoC(H2O)x–H2O xZ0

879

(1) 37.1 (2) 40.1 (3) 39.3G1.4 (4) 37.0 (5) 32.3G4.6 (1) 45.0 (2) 41.9 (3) 38.8G1.6 (4) 39.2G6.9 (3) 15.5G1.1 (3) 13.7G1.4 (6) w10.5

155.2 167.7 164.4G5.9 155 135.1G19.3 188.3 175.3 162.3G6.7 164.0G28.9 64.9G4.6 57.3G5.9 w44

CID

(1) 1989MAG/DAV(b) (2) 1989MAR/SQU (3) 1994DAL/HON (4) 2000VUK/STO (5) 2001POI/PRA

(6) Extrapolate

(6) This volume

CoC–OCH3

R69.2

R289

Ion reactions

1994CHE/CLE

CoC–S

(1) 62G5 (2) 68.9G2.1 (2) 61.9G7.8

259G21 288.3G8.7 259G33

(1) PD (2) CID

(1) 1986JAC/FRE (2) 2001RUE/ARM

(1) 23.0G1.7 (2) 61.3G2.1 (3) 59.0G1.7 (4) O42.6 (4) O59

(1) 96.2G7.1 256.6G8.7 247G7 O178 O247

(1) (2) (3) (4)

(1) 1996HEI/SCH (2) 1991CLE/ARM (3) 1996ARM/KIC (4) 1984ALL/RAD

(1) 58.8 (2) 52.3G3.8 (1) 61.1 (2) 59.8G2.6 (2) 15.5G1.4 (2) 12.2G1.4

246 219G16 256 250G11 65G6 51G6

CID

(1) 1989MAR/SQU (2) 1998WAL/ARM

CoC–CH3CN

O61G4

O255G17

PD

1988BUC/FRE

CoC–pyridine –pyrimidine

59.3G2.9 58.9G3.3

248.3G12.3 246.6G13.7

CID

2000ROD/STA 2001AMU/ROD

CoC–PCH3

66.4G2.5

278G11

CID

2005GEN/SZT

CoNOC–PCH3

62.4G3.8

261G16

Derived

2005GEN/SZT

1

2 3 N

–CS

CoC–N2 –NH2 –NHCH3 –N(C2H5)2

CoC(NH3)x–NH3 xZ0 1 2 3

FT-ICR GIB MS Review Ion reactions

(continued)

7366—CHAPTER 19—3/2/2007—11:20—BSARAVANAN—15375—XML MODEL B – pp. 855–902

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Comprehensive Handbook of Chemical Bond Energies

Table 19.1.2 (continued) BDEs of CoC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

CoCONOC–PCH3

44.9G3.8

188G16

Derived

2005GEN/SZT

Co(CO)2NOC–PCH3

40G4

167G16

Derived

2005GEN/SZT

CoC–PC2H5

80.9G3.9

339G16

CID

2005GEN/SZT

CoNOC–PC2H5

78G4.8

326G20

Derived

2005GEN/SZT

CoCONOC–PC2H5

59.8G4.8

250G20

Derived

2005GEN/SZT

Co(CO)2NOC–PC2H5

54G4.8

226G20

Derived

2005GEN/SZT

(1) 57G3 (2) 61 (1) %46G3

238G13 255 %192G13

FT-ICR

(1) 1997NAN/FRE (2) 2004GRI/MAN

(1) 59G3

247G13

(1) FT-ICR

(1) 1997NAN/FRE

(2) O66 (1) %48G3 (2) 46.4

O276 %201G13 194.1

(2) Kinetics

(2) 2000GAP/YAN

61G3

255G13

FT-ICR

1997NAN/FRE

%49G3

%205G13

64G3

268G13

FT-ICR

1997NAN/FRE

%51G3

%213G13

CoC(L)x–L, LZfuran xZ0 1

CoC(L)x–L, LZpyrrole xZ0 1

CoC(L)x–L, LZthiophene xZ0 1

CoC(L)x–L, LZselenophene xZ0 1

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BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

881

CoC–adenine

71.0G2.6

297.0G11.0

CID

2002ROD/ARM

CoC–imidazole

64.2G2.6

268.8G10.7

CID

2004RAN/AMU

CoC–Si –SiH –SiH2 –SiH3

(1) 75.8G1.6 (1) 69.9G3.7 (2) 67G6 (1) 45.2G3

317.1G6.7 292.5G15.5 280G25 189.1G12.6

GIB MS

(1) 1995KIC/ARM(b)

CoC–SiCH3 –Si(CH3)2

O60 O69

O251 O269

CID

1989HAY/KRU(b)

Co2C–OH

44G12

184G50

FAB

1993MCC/LEB

Co2C(H2O)x–H2O xZ9 10 11

15G3 15G3 14G3

62.8G12.6 62.6G12.6 58.6G12.6

HP MS

1990BLA/JAY(b)

Co2C–a-amylase

4.4

18.5

UV

2002SAB

(2) 1986HAY/KRU

19.1.3 CoK–X bonds Table 19.1.3 BDEs of CoL–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CoK–Co

(1) 42.4G3 (2) 32.0 (3) 40.7G0.2

177.4G12.6 134.0 170.1G1.0

(1) Derived (2) Derived (3) Derived from DfH0 in ref.

(1) 1985SAL/LAN (2) 1996SMI/YAT (3) 1996NIST

CoK–H

(1) 46.6G3.1 (2) 57.8G2

195G13 242G8.4

(1) Derived (2) Derived from EA in ref.

(1) 1991ARM/SUN (2) 1996NIST (continued)

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882

Comprehensive Handbook of Chemical Bond Energies

Table 19.1.3 (continued) BDEs of CoK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) CoK(CO)x–CO xZ2 3

kcal/mol (1) (2) (1) (2)

34G6 38.1G3.9 38.7G3.5 39.7G3.7

kJ/mol

Methods (reference in parentheses)

References

142G25 159.4G16.3 162G15 166.1G15.5

CID

(1) 1992SUN/SQU (2) 1993SUN/WAN

(h5-C5H5)CoK(CO)–CO

24.3G2.9

102G12

CID

1995SUN/SQU

CoK–S CoK–SH

O103 83G9

O431 347G38

Derived

1989SAL/LAN

19.2 Rh– and RhC–X bonds 19.2.1 Rh–X bonds Table 19.2.1 BDEs of Rh–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Rh–Rh

(1) (2) (3) (4)

Cl(CO)2Rh–Rh(CO)2Cl

67.9G2 68.1 35.5 56.37G0.01

Methods (reference in parentheses)

kJ/mol

MS Review Review Spectroscopy

References

284G8 285 148.4 235.85G0.05

(1) (2) (3) (4)

22.6

94.6

Calorimetry

1976PRI/DRA

(TXP)Rh–Rh(TXP) TXPZtetraxylylporphyrinato

w12

w50

Derived

1991WAY/BA

(OEP)Rh–Rh(OEP) OEPZoctaethyporphyrinate dianion

(1) 16.5G0.8 (2) 16.0 (3) 16.5

69.0G3.3 67 69.0

(1) Derived (2) Derived (3) Review

(1) 1988WAY (2) 1992WAY (3) 1994NOL

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

(1) 1974COC/GIN (2) 1979MIE/GIN (3) 1996SMI/YAT (4) 1998LAN/MOR

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

883

(ttbs)Rh–Rh(ttbs) ttbsZN,N 0 -ethyl-enebis(3,5di-tertbutylsalicylaldiminato

w13.4

w56

Kinetics

2000BUN/NI

Rh(100, surf.)–Rh

(1) 20.2G1.7 (phys) (2) 19.1 (3) 19.4

84.5G7.1 80.1 81.0

FIM

(1) 1974AYR/EHR (2) 1994KEL (3) 1994KEL(e)

Rh(100, surf.)–Rh

133

556

Review

1995SEE/ALL

Rh(100, surf.)–Rh2 –Rh3 –Rh4 –Rh5 –Rh6 –Rh7 –Rh8 –Rh9 –Rh10 –Rh11

22.4 (phys) 23.5 24.2 23.3 26.3 24.0 26.3 28.1 24.7 28.4

93.6 98.4 101.3 97.4 110.0 100.3 110.0 117.7 103.2 118.7

FIM

1994KEL(e)

Rh(110, surf.)–Rh Rh(111, surf.)–Rh Rh(311, surf.)–Rh Rh(331, surf.)–Rh

13.9G0.8 (phys) 3.6G0.5 12.4G1.2 14.8G0.9

58.2G3.3 15.1G2.1 51.9G5.0 61.9G3.8

FIM

1974AYR/EHR

Rh(100, surf.)–Ir

19.1 (phys)

80.1

FIM

1994KEL(d)

Rh–Ba

62.0G6.0

259.4G25

MS

1978GIN/CHO

Rh–Sc –Y –La –Ce –Eu

106.0G2.6 106.6G2.6 131.5G2.9 130.3G1.7 56.9G8

444G11 446G11 550G12 545G7 238G34

MS

1989CHA/GIN

Rh–Th –U

122.6G5 124.0G4

513G21 519G17

MS

1978GIN/GUP

Rh–Ti –V

93.4G3.5 86.9G6.9

390.8G14.6 363.6G29

Review

1986MOR

(continued)

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

884

Comprehensive Handbook of Chemical Bond Energies

Table 19.2.1 (continued) BDEs of Rh–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

Methods (reference in parentheses)

kcal/mol

kJ/mol

Rh(100, surf.)–Pt Rh(100, surf.)–Pt2 Rh(100, surf.)–Pt3 Rh(100, surf.)–Pt4 Rh(100, surf.)–Pt5 Rh(100, surf.)–Pt6

21.2G3 (phys) 21.2 23.8 23.8 23.8 26.7

88.8G12.5 88.8 99.4 99.4 99.4 111.9

FIM

1993KEL

Rh(100, surf.)–Pt

134

561

Review

1995SEE/ALL

Rh(110, surf.)–Pt Rh(111, surf.)–Pt Rh(311, surf.)–Pt Rh(331, surf.)–Pt

15.0 (phys) !5.1 10.1G1.2 16.6G0.5

62.7 !21.2 42.5G4.8 69.5G1.9

FIM

1993KEL(b)

Rh–Au

55.6G7

232.6G29

Review

1986MOR

Rh(110, surf.)–He

w0.19

w0.79

HAS

1989PAR/KIR

Rh–H

(1) O47 (2) 59G5 (3) 56.7G1.4

O197 247G21 237.2G5.9

(1) Ion reactions (2) Ion reactions (3) CID

(1) 1984JAC/BYR (2) 1986TOL/BEA (3) 1995CHE/ARM(b)

Rh(polycs. surf.)–H

61

255

Review

1979TOY/SOM

Rh(100, surf.)–H

12.0 (phys)

50.2

TPD

1987RIC/HO

Rh(110, surf.)–H

4–5 (phys)

17–21

Review

1988SEE/KON

Rh(110, surf.)–D

4–5.5 (phys)

17–23

Review

1988SEE/KON

Rh(110, surf.)–T

5–6 (phys)

21–25

Review

1988SEE/KON

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

References

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

885

Rh(110, surf.)–H

(1) 62.4 (2) 61

261 255

(1) TDS (2) Review

(1) 1988EHS/CHR (2) 1991BEN

Rh(111, surf.)–H

(1) 63 (2) 61

264 255

Review

(1) 1979ERT (2) 1991BEN

Rh(1010, surf.)–H

13.4 (phys a-state) 19.1 (b-state)

56 80

TDS

1989LAU/SCH

Rh(OEP)–H OEPZoctaethyporphyrinate dianion

61.8

258.6

Kinetics

1988WAY

(TXP)Rh–H, TXPZ tetraxylylporphyrinato (TMP)Rh–H, TMPZtetramesitylporphyrinate dianion (dbpb)Rh–H, dbpbZ4,5dimethyl-1,2bis(1-butylpentyl)pyridine-2-carbo-xamido)benzene dianion

(1) 60

251

Derived

(1) 1991WAY/BA

(1) 60

251

(2) w60

w251

(F28TPP)Rh–H, F28TPP is an abbreviation, see the ref.

58G2

242.7G8.4

Derived

2000NEL/DIM

HRh(m-xylyl)Rh–H

61.1G0.4

255.6G1.7

Derived

2004CUI/WAY

Rh–O

97G10

405G42

Review

1990SIM/BEA

Rh(surf.)–O

87

364

TPD

1994MAD/ROB

Rh(100, surf.)–O

(1) 102.1 (2) 107.1

427 448.1

(1) Calorimetry (2) Review

(1) 1998BRO/KOS (2) 2003ZEI

Rh(110, surf.)–O

110.2

461.1

Review

2003ZEI

(2) 1996WEI/WAY

(continued)

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

886

Comprehensive Handbook of Chemical Bond Energies

Table 19.2.1 (continued) BDEs of Rh–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Rh(111, surf.)–O

4.3G0.7 (phys)

18.0G2.9

TPD

1995PET/SIB

Rh(111, surf.)–O

(1) 87.5 (2) 102.0

366 426.8

Review

(1) 1991BEN (2) 2003ZEI

Rh(100, surf.)–N

121.8

509.6

Review

2003ZEI

Rh(110, surf.)–N

(1) 113–120 (2) 125.3

473–502 524.3

(1) TPD (2) Review

(1) 1992LIZ/COM (2) 2003ZEI

Rh(111, surf.)–N

116.0

485.3

Review

2003ZEI

Rh–P

84.4G4

353.1G16.7

MS

1971SMO/HUG

Rh–C –C2

138.6G1 103.5

580G4 433

Review

1990SIM/BEA

Rh–Si

94.4G4.3

395.0G18.0

MS

1970MAH/PEE

Rh–B

113.7G5

475.8G21

MS

1970MAH/PEE

(PiPr3)2(Cl)Rh–H2

32.5

136.0

Calorimetry

1995WAN/ROS

Rh(polycr. surf.)–H2

(1) 27.5 (2) 18

115 75

(1) Calorimetry (2) FDMS

(1) 1950BEE//COL (2) 1966MIM/HAN

Rh(100, surf.)–D2

19.1G0.4

79.9G1.7

TDS

1982KIM/PEE

Rh(111, surf.)–H2 –D2

3.7–4.3 (phys) 4.3

15.4–18 18

LITD

1988SEE/KON

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

887

Rh(111, surf.)–H2

(1) 18.6 (2) 19 (3) 17.2

77.8 79 72

(1) TDS (2) TRP (3) TPD

(1) 1979YAT/THI (2) 1985ROO/SCH (3) 1997HAR/SAN(b)

Rh(111, surf.)–D2

13.8G2

57.7G8.4

LITD

1992MAN/SET

Rh(polycr. surf.)–O2

(1) 116.2 (2) 102 (3) 43.5

486 427 182

(1) Calorimetry (2) Calorimetry (3) Review

(1) 1960BRE/HAY (2) 1965BRE/HAY (3) 1982RAO/KAM

Rh(100, surf.)–O2

(1) 86 (2) 92.3

360 386

(1) TPD (2) Calorimetry

(1) 1983FIS/SCH (2) 1998KOS/BRO

Rh(111, surf.)–O2

24 (phys)

100

TPD

1983ROO/SCH

Rh(111, surf.)–O2

(1) 56G2 (2) 85G5 (3) 56G2

234.3G8.4 356G21 234.3G8.4

TPD

(1) 1979THI/YAT (2) 1983ROO/SCH (3) 1995PET/SIB

Rh(100, surf.)–N2

9 (phys)

38

Correlation

1981NIE

Rh(100, surf.)–N2

(1) 39.4 (2) 53.8G1.2

165 225G5

TPD

(1) 1997JAN/CHO (2) 2000HOP/NIE

Rh(110, surf.)–N2

10 (phys)

42

Correlation

1981NIE

Rh(110, surf.)–N2

(1) 21.5–31 (2) 29.6

90–130 123.8

TPD

(1) 1992COM/LIZ (2) 1995PED/BEL

Rh(110, 1!1, surf.)–N2

21.0 (a-state) 27.5 (b1-state)

88 115

TPD

1993KIS/LIZ

Rh(110, 1!2, surf.)–N2

28.2 (b2-state)

118

TPD

1993KIS/LIZ

Rh(111, surf.)–N2

8 (phys)

33

Correlation

1981NIE

(continued)

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

888

Comprehensive Handbook of Chemical Bond Energies

Table 19.2.1 (continued) BDEs of Rh–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Rh(111, surf.)–N2

(1) (2) (3) (4) (5)

Rh(431, surf.)–N2 Rh(533, surf.)–N2

(PiPr3)2(Cl)Rh–N2

Rh(100, surf.)–NO

31 29.0 28.2G2.4 32.1 28.2G2.4

kJ/mol

Methods (reference in parentheses)

References

130 121.3 118G10 134.3 118G10

TPD

(1) 1986OH/FIS (2) 1993BEL/DIM (3) 1994BOR/REI (4) 1995PED/BEL (5) 2000HOP/NIE

23.9

100

TPD

1997JAN/CHO

16.7

70

16.5

69.0

Calorimetry

1995WAN/ROS

(1) 25

104.6

(1) TPD

(1) 1984HO/WHI

(2) 28G3 (3) 10.5G0.7 (4) 8.8G1.2

117.2G12.6 43.9G2.9 37G5

(2) TPD (3) TPRS (4) TPD

(2) 1987VIL/HO (3) 1988WHO/HO (4) 2000HOP/NIE

Rh(110, surf.)–NO

31.1G1.4

130G6

TPD

1994SCH/JIR

Rh(111, surf.)–NO

(1) (2) (3) (4) (4) (5)

130 109 112–124 113G10 65G6 65G6

TPD

(1) 1983ROO/SCH (2) 1986OH/FIS (3) 1987BUG/SOL (4) 1994BOR/REI

31 26 26.8–29.6 27.0G2.4 15.5G1.4 (dis.) 15.5G1.4

(5) 2000HOP/NIE

Rh(101, surf.)–NO

w24.6

w103

TPD

1978REE/COM

(PiPr3)2(Cl)Rh–CO

48.2

201.7

Calorimetry

1995WAN/ROS

Rh(polycr. surf.)–CO

7G1 (phys)

29G4

NMR

1989DUN/THA

Rh(polycr. surf.)–CO

(1) 46 (2) R44

192 R184

(1) Calorimetry (2) IR

(1) 1965BRE/HAY (2) 1967KAV/SOK

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

889

Rh(100, surf.)–CO

(1) (2) (3) (4) (5)

29 31.8G1.0 31.3G1 32.3G1.8 28.4G1

121.1 133.1G4 131G4 135.1G7.5 118G4

(1) (2) (3) (4) (5)

TPD TPD TPD EELS Calorimetry

(1) 1978CAS/SEX (2) 1982KIM/PEE (3) 1994JON/NIE (4) 1997WEI/SKE (5) 1999KOS/BRO(c)

Rh(110, surf.)–CO

(1) (2) (3) (4)

w31.1 31.5 31.1G1.4 39.2G1.4

w130 132 130G6 164.0G5.9

(1) (2) (3) (4)

TPD TPD TPD EELS

(1) 1977MAR/LAM (2) 1991BOW/GUO (3) 1994SCH/JIR (4) 1997WEI/SKE

Rh(111, surf.)–CO

7.1 (phys)

29.7

LITD

1988SEE/KON

Rh(111, surf.)–CO

(1) (2) (3) (4) (5)

132.2 130 132.2 135.1 164.8G2.5

(1) (2) (3) (4) (5)

(1) 1979THI/WIL (2) 1985ROO/SCH (3) 1986OH/FIS (4) 1991PET/CUR (5) 1997WEI/SKE

Rh(111, 2!2, surf.)–CO

w34.6

w144.7

Photoemission

2001SME/BEU

Rh(1000, surf.)–CO

24–27 (a-state) 50 (b-state)

100–113 209

TDS

1977HOU/DUC

Rh(1010, surf.)–CO

(1) 25 (2) 23–28

104 95–118

TPD

(1) 1988KEL/GEL (2) 2004PAU/PRZ

Rh(311, surf.)–CO

31.1

130

TDS

1993BAT/GAR

Rh(polycs. surf.)–CO2

5.4 (phys)

23

Review

1983WEI

Rh(polycs. surf.)–CO2

26.0

109

Review

1983WEI

Rh(110, surf.)–CO2

28.0

117.2

TPD

1995PED/BEL

Rh(111, surf.)–CO2

14.3 (phys)

59.8

TPD

1986OH/FIS

31.6 31 31.6 32.3 39.4G0.6

TPD TPRS TPD Scattering Mol. beam

(continued)

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

890

Comprehensive Handbook of Chemical Bond Energies

Table 19.2.1 (continued) BDEs of Rh–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Rh(111, surf.)–CO2

34.2

143.1

TPD

1995PED/BEL

Rh(111, surf.)–ON2

35.7

149.4

TPD

1995PED/BEL

Rh(110, surf.)–ON2

25.3

105.9

TPD

1995PED/BEL

Rh(111, surf.)–H2O

10.8

45.2

TPD

1987WAG/MOY

Rh(111, surf.)–HCN

50.2G3.6

210G15

SIMS/TPD

1997HAR/SAN

Rh(111, surf.)–NH3

19.5G0.7

81.5G3

SIMS/TPD

1996HAR/SAN

(L)Rh–CH3, LZTMPZ etramesi-tylporphyrinate dianion LZTXPZ tetraxylylporphyrinato

57.8

242

Derived

1992WAY

56.9

238

CH3–Rh(ttp), ttpZ5,10,15,20tetratolylporphyrin CH3–Rh(tmp) tmpZ5,10,15,20-tetramessityl-porphyrin

54.3

227

PAC

2001LI/ZHA

52.3

219

HRh(m-xylyl)Rh–CH3

56.7G1.8

237.2G7.5

Derived

2004CUI/WAY

Rh(surf.)–CH4

11.1G1.3

46.4G5.4

Chemisorption

1987BRA/EHR

HRh(m-xylyl)Rh–CH2OH

46.7G1.8

195.4G7.5

Derived

2004CUI/WAY

Rh(111, surf.)–CH3OH

11.5

48

TDS

1984SOL/BER

Rh(111, surf.)–CH2I2

13.1

54.9

TPD/AES

1995KLI/SOL

Rh(100, surf.)–CaCH

w64

w268

Calorimetry

1999KOS/BRO(b)

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

891

Rh(100, surf.)–C2H2

50.2G2.4

210G10

Rh(polycr. surf.)–C2H4

42.4

177

Calorimetry

1950BEE/COL

Rh(100, surf.)–C2H4

41.8G2.4

175G10

Calorimetry

1999KOS/BRO(b)

(h5-C5H5)Rh(C2H4)–C2H4

!31

!130

Kinetics

1971CRA

(PiPr3)2(Cl)Rh–C2H4

24.8

103.8

Calorimetry

1995WAN/GOL

(TMP)Rh–C2H5, TMPZtetramesitylporphyrinate dianion

48.5

203

Derived

1992WAY

HRh(m-xylyl)Rh–C2H5

50.0G1.8

209.2G7.5

Derived

2004CUI/WAY

Rh(OEP)–C(O)H, OEPZ octaet-hyporphyrinate dianion

(1) 58 (2) 59.5

242.7 249

(1) Kinetics (2) Re-cal.

(1) 1988WAY/COF (2) 1992WAY

Rh(OEP)–CH(OH)Bu OEPZ octaethyporphyrinate dianion

44.0

184

Derived

1992WAY

(PiPr3)2(Cl)Rh–MeCCMe –tBuNC

20.6 42.4

86.2 177.4

Calorimetry

1995WAN/GOL

Rh(111, surf.)–PhOH

w14

w59

TPR

1989XU/FRI

(TMP)Rh–CH2C6H5, TMPZ tetramesitylporphyrinate dianion

33

138

Derived

1992WAY

HRh(m-xylyl)Rh–CH2C6H5

37.1G1.8

155.2G7.5

Derived

2004CUI/WAY

(continued)

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

892

Comprehensive Handbook of Chemical Bond Energies

Table 19.2.1 (continued) BDEs of Rh–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(PiPr3)2(Cl)Rh–PhCCPh

22.8

95.4

Calorimetry

1995WAN/GOL

(OEP)Rh–C(O)Rh(OEP) OEPZoctaethyporphyrinate dianion

49G3

205G13

Derived

1988COF/BRE

(OEP)Rh– CH2CH(CH3)Rh(OEP) OEPZoctaethyporphyrinate dianion

w45

w188

Derived

1989WAY/FEN

Rh(NC3H3C6H3C(O)(Cl)(py) C(Ph)(OMe)H

31

130

Kinetics

1986SUG/JUN

19.2.2 RhC–X bonds Table 19.2.2 BDEs of RhD–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

RhC–H

(1) 42G3 (2) 39.4G0.9

176G13 164.8G3.8

Ion reactions

(1) 1984MAN/HAL (2) 1995CHE/ELK

RhC(C)–H RhC(CH)–H

20G24 89G5

84G100 372G21

Ion reactions

1986HET/FRE

(1) 89G5 (2) 80G5 (3) 68.6G2.9

372G21 335G21 287G12

(1) PD (2) Thermochem. (3) Review

(1) 1987HET/JAC (2) 1981STE/BEA (3) 1990SIM/BEA

(1) O120 (2) 98.9G4.2 (1) 102G7

O502 414G17 427G29

(1) PD (2) GIB MS

(1) 1987HET/JAC (2) 1995CHE/ARM(b)

(L)RhC–H LZCH (h5-C5H5)(CO)2

RhC–C –CH

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

–CH2

RhCoC–CH2 RhFeC–CH2

(2) (1) (2) (3)

106.1G2.8 89G5 85.1G1.8 91G5

444G12 372G21 356G8 381G21

893

(3) Ion reactions

(3) 1985JAC/FRE(c)

78–93 78–93

326–389 326–389

PD

1987HUA/BUC

(1) 47G5 (2) 33.9G1.4 (3) O49

197G21 142G6 O205

(1) Ion reactions (2) GIB MS (3) Review

(1) 1984MAN/HAL (2) 1995KIC/ARM(c) (3) 1990SIM/BEA

(1) 38.5G0.7

161G3

(1) CID

(1) 1995CHE/ARM(b)

(1) O30.9G0.2 (2) 31 (1) 41.5G4.2

O129G1 129.7 174G17

(2) Review

(2) 1998SCH/SCH

FeRhC–C2H2 FeRhC–C2H4

O24 O45

O100 O188

PD

1987HUA/BUC

RhC–C3H4 –C3H6

53.0G4.6 28.1

222G19 118

CID

1995CHE/ARM(b)

FeRhC–C3H4 CoRhC–C3H4

O33 O33

O138 O138

PD

1987HUA/BUC

RhCoC–C3H8 RhFeC–C3H8

O30 O30

O126 O126

PD

1987HUA/BUC

RhC–C4H6

O56

O236

Review

1990SIM/BEA

FeRhC–C4H6 CoRhC–C4H6

O56 O56

O236 O236

PD

1987HUA/BUC

RhC(CH3)x–CH3 xZ0 1

RhC–C2H2 –C2H4 –C2H5

(continued)

7366—CHAPTER 19—3/2/2007—11:21—BSARAVANAN—15375—XML MODEL B – pp. 855–902

894

Comprehensive Handbook of Chemical Bond Energies

Table 19.2.2 (continued) BDEs of RhC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

RhC–cyclo-C5H5

162–189

678–791

PD

1987HUA/BUC

CoRhC–C5H6 FeRhC–C5H6

O67 O67

O280 O280

PD

1987HUA/BUC

CoRhC–cyclo-C5H6 FeRhC–cyclo-C5H6

O50 O50

O209 O209

PD

1987HUA/BUC

RhC–C6H6

66G7

276G29

Review

1990SIM/BEA

CoRhC–C6H6 FeRhC–C6H6

49–60 49–60

205–251 205–251

PD

1987HUA/BUC

(1) !85 (2) 70.5G1.4 (3) 78

!356 295.0G5.8 326

(1) Ion reactions (2) Ion reactions (3) Derived

(1) 1987HET/FRE (2) 1995CHE/ARM(c) (2) 2000SCH/SCH

FeRhC–O CoRhC–O

O85 O85

O356 O356

PD

1987HUA/BUC

RhC–NO

40G5

167G21

Ion reactions

1985CAS/FRE

[(bipyridine)RhC]–PCH

46.5G3.5

194.6G14.6

CID

2001KIM/CHE

RhC–S

54.0G3.1

226G13

Ion reactions

2003ARM

RhC–CS

55.9G4.5

234G19

CID

2000ROD/ARM

(bipyridine)RhC–PCH

46.6G3.5

194.9G14.5

CID

2000KIM/CHE

RhC(O)x–O xZ0 1

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BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

895

19.3 Ir– and IrC–X bonds 19.3.1 Ir–X bonds Table 19.3.1 BDEs of Ir–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ir–Ir

86G16

361G68

Review

1986MOR

Ir(100, surf.)–Ir

(1) 19.4G1.2 (phys) (2) 31.1G1.8 (edge) (2) 32.3G1.6 (step)

81.0G4.8 130.3G7.7 135.1G6.8

FIM

(1) 1990CHE/TSO (2) 1993CHO/TSO

Ir(100, surf.)–Ir

150

628

Review

1995SEE/ALL

Ir(110, surf.)–Ir

(1) 17.0 (2) 16.4G0.5

71.1 68.5G1.9

FIM

(1) 1991EHR (2) 1991TSO/CHE

Ir(111, surf.)–Ir

(1) 5.1G0.7 (phys) (2) 6.2G0.1

21.2G2.9 25.7G0.4

FIM

(1) 1990CHE/TSO(b) (2) 1990WAN/EHR

Ir(111, surf.)–Ir2 Ir(111, surf.)–Ir3 Ir(111, surf.)–Ir4 Ir(111, surf.)–Ir5

9.8G0.3 (phys) 14.4G0.4 10.5G0.3 15.3G0.3

41.0G1.3 60.2G1.7 43.9G1.3 64.0G1.3

FIM

1990WAN/EHR

Ir(polycs. surf.)–Cs –CsC

54.9G2.3 48.4G1.2

229.6G9.6 202.6G4.8

Mol. beam

1991HAN/PET

Ir(111, surf.)–Ba

133.7

559.6

FIM

1977ZAN/RUT

Ir–Y

(1) 110.4G4.6 (2) 109.2G3.6

461.9G9.6 457G15

(1) Review (2) MS

(1) 1986MOR (2) 1989CHA/GIN

Ir–La

137.9G3

577G12

MS

1989CHA/GIN

Ir–Ce

137.4G2.2

575G9

MS

1989CHA/GIN

(continued)

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896

Comprehensive Handbook of Chemical Bond Energies

Table 19.3.1 (continued) BDEs of Ir–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ir(111, surf)–Yb

110.7G4.6

463.1G19.3

FIM

1975ION/MED

Ir–Th

137.3G10

574G42

MS

1974GIN

Ir–Ti

100.9G3.1

422G13

MS

1989PEL/GIN

Ir–Nb

111G6

465G25

Review

1986MOR

Ir(111, surf.)–W

7.3 (a-state) 11.7 (b-state)

30.5 49.0

FIM

1992WAN/EHR

Ir(100, surf.)–Re

22

92

FIM

1992TSO/CHE

Ir(100, surf.)–Re

180

753

Review

1995SEE/ALL

Ir(111, surf.)–Re

8.7 (phys a-state) 12.0 (b-state)

36.4 50.2

FIM

1992WAN/EHR

Ir(Cl)(CO)(PMe3)2–H

60

251

Review

1988STO/BER

Ir(Cl)2(CO)(PPh3)2–H Ir(Cl)(Br)(CO)(PPh3)2–H

58.6 56.6

245 237

Review

1990SIM/BEA

Ir(Cl)2(CO)(PMePh2)2–H

63.6

266

Ir(H)(h5-C5Me5)(PMe3)–H

74.2G5

310.5G21

Kinetics, PAC, Calorimetry

1987NOL/HOF

Ir(Cl)(H)(CO)(PR3)2–H RZEt

58.1

243.1

Review

1994NOL

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BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

c-C6H11

897

58.8

246.0

Ir(Cl)(H)(CO)(PEt3)2–H

58.1

243.1

Review

1994NOL

Ir(X)(H)(CO)(PPh3)2–H XZCl Br I

59.0 60.5 61.7

246.9 253.1 258.2

Review

1994NOL

Ir(polycs. surf.)–H

64

268

Review

1979TOY/SOM

Ir(100, surf.)–H

10.6 (phys)

44.4

TDS

2006LER/KLE

Ir(110, surf.)–H

63.1

264

Review

1998CHR

Ir(111, surf.)–H

(1) 63 (2) 58

264 243

Review

(1) 1974ERT (2) 1998CHR

90.3G5

377.8G21

1987NOL/HOF

76.0G5 63.8G5

318.0G21 266.9G21

Kinetics, PAC, Calorimetry

Ir–O

99G10

414G42

Review

1990SIM/BEA

Ir(surf.)–O

89

372

TPD

1994MAD/ROB

Ir(100, surf.)–O Ir(110, surf.)–O Ir(111, surf.)–O

97.7 100.4 93.0

409 420 389

Review

2003ZEI

Ir(100, surf.)–N

133.4

558.1

Review

2003ZEI

Ir(110, surf.)–N

(1) 91.5 (2) 137.2

383 574.0

Review

(1) 1991BEN (2) 2003ZEI

Ir(X)(h5-C5Me5)(PMe3)–X XZCl Br I

(continued)

7366—CHAPTER 19—3/2/2007—11:22—BSARAVANAN—15375—XML MODEL B – pp. 855–902

898

Comprehensive Handbook of Chemical Bond Energies

Table 19.3.1 (continued) BDEs of Ir–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Ir(111, surf.)–N

(1) 92.0 (2) 127.0

385 531.4

Ir–B

122.4G4.1

512.2G17

MS

1970MAH/PEE

Ir–C –C2

150.8G1.2 132.6

631G5 555

Review

1990SIM/BEA

Ir–Si

110.6G5

462.8G21

MS

1970MAH/PEE

Ir(dmpe)2–H2 dmpeZ1,2-bis(dimethyl)phos-phinoethane

64.0G1

267.8G4.2

PAC

1993BEL/SCA

(Cl)(CO)(PPh3)2Ir–H2

15.0

62.8

Calorimetry

1992HOF

Ir(polycs. surf.)–H2

24

100.4

FDMS

1966MIM/HAN

Ir(110, surf.)–H2

17

71

TDS

1980IBB/WIT

Ir(111, surf.)–D2

18

75.3

TDS

1987ENG/TSA

Ir(100, 1!1, surf.)–D2 Ir(100, 1!5, surf.)–D2

23.4G3.3 20.3

98G14 85

Mol. beam

1998ALI/WAL

(Cl)(CO)(PPh3)2Ir–O2

17.1

71.5

Calorimetry

1992HOF

Ir(polysc. surf.)–O2

38.1G3 (phys)

159G13

TD

1972AGE/ION

Ir(polysc. surf.)–O2

(1) 71.5G2 (2) 40

299G8 168

(1) TD (2) Review

(1) 1972AGE/ION (2) 1982RAO/KAM

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BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

899

Ir(111, surf.)–O2

65G3

272G13

TD

1976IVA/BOR

(Cl)(CO)(PPh3)2Ir–CO

10.8

45.2

Calorimetry

1992HOF

Ir(polycs. surf.)–CO

O50

O209

IR

1967KAV/SOK

Ir(100, 1!1, surf.)–CO Ir(100, 1!5, surf.)–CO

46.8G1.2 35.9

196G5 150

Calorimetry

1998ALI/KLO

Ir(110, surf.)–CO

37

155

TDS

1978TAY/IBB

Ir(110, 2!1, surf.)–CO

29.5

123.4

TDS

1978NIE/SOM

Ir(111, surf.)–CO

(1) (2) (3) (4)

146.4G8 163G15 140 w175

(1) TDS (2) TDS (3) Review (4) TR-IRAS

(1) 1976COM/WEI (2) 1976HAG/NIE (3) 1978MAD/BEN (4) 1997SUS/LAU

Ir(polycs. surf.)–N2

58

243

TD

1966MIM/HAN(b)

Ir(100, surf.)–N2

(1) 7–14 (phys) (2) 15.3

29–59 64

(1) FEM (2) TPD

(1) 1973NIE/MEI (2) 2002SAN/MIN

Ir(110, surf.)–N2

(1) 8.5 (phys) (2) 10

36 42

(1) LEED (2) Correlation

(1) 1981IBB/WIT(b) (2) 1981NIE

Ir(110, surf.)–NO

36–45

151–188

TPD

1981IBB/WIT

Ir(111, surf.)–NO

20

48

Review

1979ERT

(Cl)(CO)(PPh3)2Ir–SO2

10.1

42.3

Calorimetry

1992HOF

Ir(Cl)2(CO)(PMe3)2–CH3

35.4

148.1

Review

1988STO/BER

35G1 39G3 33.5 w41.8

(continued)

7366—CHAPTER 19—3/2/2007—11:22—BSARAVANAN—15375—XML MODEL B – pp. 855–902

900

Comprehensive Handbook of Chemical Bond Energies

Table 19.3.1 (continued) BDEs of Ir–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ir(CH3)(h5-C5Me5)(PMe3)–CH3

(1) 56 (2) 58.0G0.8

234 242.7G3.3

Review

(1) 1988STO/BER (2) 1994NOL

Ir(H)(h5-C5Me5)(PMe3)–C2H3

71.0

297.1

Review

1992DRA/WON

(Cl)(CO)(PPh3)2Ir–C2H4

11.8

49.4

Calorimetry

1992HOF

Ir(111, surf.)–C2H6 –C2D6 –C3H8 –CH3CD2CH3 –C3D8

10.4G0.3 10.9G0.3 11.4G0.3 11.6G0.3 12.0G0.3

43.5G1.3 45.6G1.3 47.7G1.3 48.5G1.3 50.2G1.3

QP-MS

1995JOH/WEI

Ir(F)(CO)(PPh3)3–C2F4 –C4F6

18.9 23.7

79 99

Review

1990SIM/BEA

Ir(Cl)(CO)(PPh3)3–C2F4 –C4F6

16.0 22.9

67 96

Review

1990SIM/BEA

Ir(Br)(CO)(PPh3)3–C2F4 –C4F6

9.8 18.9

41 79

Review

1990SIM/BEA

Ir(I)(CO)(PPh3)3–C2F4 –C4F6

13.6 19.6

57 82

Review

1990SIM/BEA

Ir(H)(h5-C5Me5)(PMe3)–nC4H9

52.0

217.6

Review

1992DRA/WON

Ir(111, surf.)–nC4H10 –(CH3)3CH –(CH3)3CD –(CD3)3CH –(CH3)4

11.5G0.3 11.3G0.3 11.5G0.3 11.7G0.3 11.3G0.3

48.1G1.3 47.3G1.3 48.1G1.3 49.0G1.3 47.3G1.3

QP-MS

1995JOH/WEI

(C(O)CF3)(PPh3)2(Cl)2Ir–L LZCH3CN Et2NH C5H10NH

16.9G0.2 3.7G0.2 12.0G0.6

70.7G0.8 15.5G0.8 50.2G2.5

Calorimetry

1992HOF

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BDEs of Co(CoG)–, Rh(RhC)–, and Ir(IrC)–X Bonds

901

(C(O)CF3)(PPh3)2(Cl)2Ir–L LZpyridine 4-CH3–pyridine

17.7G0.9 18.6G0.3

74.1G3.8 77.8G1.3

Calorimetry

1992HOF

(C(O)CF3)(PPh3)2(Cl)2Ir–L LZCH3S(O)CH3 tetrahydrofuran

18.4G0.4 !4.4G1.3

77.0G1.7 !18.4G5.4

Calorimetry

1992HOF

(1) (2) (3) (1) (2)

337.2G15 321 343.1 212.5G7 218

(1) Calorimetry (2) Review (3) Review

(1) 1987NOL/HOF (2) 1990SIM/BEA (3) 1992DRA/WON

Ir(H)(h5-C5Me5)(PMe3)–C6H5 –c-C6H11

80.6G3.6 76.7 82.0 50.8G1.7 52.1

Ir(R)(h5-C5Me5)(PMe3)–L LZc-C5H9 C5H11 2,3-Me2Bu CH2CMe2Et

51.4 58.3 57.4 !55.7

215 244 240 !233

Review

1990SIM/BEA

(C(O)CF3)(PPh3)2(Cl)2Ir–L LZP(OCH3)3 P(OCH3)2CC2H5

21.0G0.6 23.4G0.9

87.9G2.5 97.9G3.8

Calorimetry

1992HOF

19.3.2 IrC–X bonds Table 19.3.2 BDEs of IrD–X Bonds

The broken bonds (boldfaceZdissociated fragment) IrC–H –D

(CO)(h5-C5H5)(L)IrC–H LZP(p-C6H4CF3)3 P(p-C6H4F)3 PPh3 PPh2Me PMe2Ph PMe3

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

References

(1) 66.7 (2) 73.1G1.4 (2) 72.4G1.4

279.1 305.7G5.8 302.8G5.8

(1) Review (2) GIB MS

(1) 1990OHA/GOD (2) 2005LI/ZHA

75.1 75.3 74.9 75.2 75.3 75.0

314.2 315.1 313.4 314.6 315.1 313.8

Electrochemical

1996WAN/ANG

(continued)

7366—CHAPTER 19—3/2/2007—11:22—BSARAVANAN—15375—XML MODEL B – pp. 855–902

902

Comprehensive Handbook of Chemical Bond Energies

Table 19.3.2 (continued) BDEs of IrC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

74.3 74.2

310.9 310.5

(CS)(h5-C5H5)PPh3IrC–H

71.6

299.6

Electrochemical

1996WAN/ANG

(COD)(L)IrC–H LZh5-C5H5 h5-C5MeH4 1,3,5-C5Me3H2 C5Me4H CODZ1,5-cyclooctadiene

72.0 71.5 72.2 71.6

301.2 299.2 302.1 299.6

Electrochemical

1996WAN/ANG

71.3 72.9 72.3 72.4 74.0 74.8 72.2

298.3 305.0 302.5 302.9 309.6 313.0 302.1

Electrochemical

1996WAN/ANG

IrC–C

(1) 140G20 (2) 130G23

586G84 544G96

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1998NIST

IrC–CH2

O111

O464

FT-ICR

1991IRI/BEA

IrC–C2H4

56

234.3

Review

1998SCH/SCH

(1) 59 (1) 125 (2) !119

247 523 !498

Derived

(1) 2000SCH/SCH

PEt3 PCy3

(CO)(L)(h5-C5Me5)IrC–H LZCO PMe3 PPh2Me PPh3 P(p-C6H4CF3)3 P(p-C6H4Cl)3 1,5-cyclooctadiene

IrC(O)x–O xZ0 1

7366—CHAPTER 19—3/2/2007—11:22—BSARAVANAN—15375—XML MODEL B – pp. 855–902

(2) 2004LAV/BLA

chapter twenty

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X bonds 20.1 Ni–, NiC–, and NiK–X bonds 20.1.1 Ni–X bonds Table 20.1.1 BDEs of Ni–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) Ni–Ni

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 54.5

228

(1) MS

(2) 55.6

233

(2) Review

(1) 1964KAN (2) 1979MIE/GIN

(3) 47.98G0.05

200.74G0.19

(3) Spectroscopy

(3) 1995PIN/LAN

(4) 40.1

167.7

(4) Review

(4) 1996SMI/YAT

(5) 48.8

204

(5) Review

(5) 2001ARM

(1) Review

(1) 2001ARM

Ni(Ni)x–Ni xZ1

(1) 20.8

87

2

(1) 37.8

158

3

(1) 65.0

272

4

(1) 79.8

334

5 6

(1) 54.3 (1) 64.8

227 271

7

(1) 65.5

274

8

(1) 65.7

275

9

(1) 67.6

283

10

(1) 79.8

334

11

(1) 84.4

353

12

(1) 71.2

298

13

(1) 79.6

333

(continued)

903

7366—CHAPTER 20—3/2/2007—11:32—SHANMUGAM—15376—XML MODEL B – pp. 903–966

904

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.1 (continued) BDEs of Ni–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

14

(1) 81.3

340

15

(1) 84.8

355

16

(1) 81.0

339

N

(2) 102.4

428

(2) Review

(2) 1994ARM/HAL

(3) w88.4

w370

(3) Extrapolate

(3) This volume

Ni(100, surf.)–Ni

14.5 (phys)

60.8

FIM

1980TUN/GRA

Ni(100, surf.)–Ni

120

502

Review

1995SEE/ALL

Ni(110, surf.)–Ni

Ni(111, surf.)–Ni

Ni(111, surf.)–Ni

(1) 7.4 (phys)

30.9

(1) FIM

(1) 1980TUN/GRA

(2) 9.8–12.4

40.9 – 51.7

(2) HAS

(2) 1997GRA/SIL

(3) 14.9G0.6

62.2G2.5

(3) HAS

(3) 1998SIL/GRA

(1) 7.6 (phys)

31.8

(1) FIM

(1) 1980TUN/GRA

(2) 12.4G0.9

51.7G3.9

(2) HAS

(2) 2001GRA/TOE(b)

123

515

Review

1995SEE/ALL

FIM

1980TUN/GRA

Ni(311, surf.)–Ni

6.9G0.7 (phys)

28.9G2.9

Ni(331, surf.)–Ni

10.3G1.5

43.1G6.3

Ni–Pd

33.7

140.9

Spectroscopy

1990TAY/SPA

Ni–Pt

65.4G0.1

273.7G0.3

Spectroscopy

1990TAY/SPA(b)

Ni(100,surf.)–Pt

15.9 (phys)

66.6

FIM

1992KEL

Ni(100,surf.)–Pt

137

573

Review

1995SEE/ALL

7366—CHAPTER 20—3/2/2007—11:32—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

905

Ni(110,surf.)–Pt

6.5 (phys)

27.0

FIM

1991KEL

Ni(110,surf.)–Pt

130

544

Review

1995SEE/ALL

Ni(111,surf.)–Pt

!5.1 (phys)

21.2

FIM

1992KEL

Ni(311,surf.)–Pt

8.8 (phys)

36.7

FIM

1992KEL

Ni(311,surf.)–Pt

137

573

Review

1995SEE/ALL

AlNi(110,surf.)–Pt

11.1

46.3

FIM

2001NIL/COR

TDS

1970GER/RHO

TDS

(1) 1970GER/RHO

Ni(100, surf.)–Na

58.1G2.3

243.1G9.6

Ni(110, surf.)–Na

50.3G2.3

210.3G9.6

Ni(111, surf.)–Na

(1) 58.6G2.3

245.1G9.6

(2) 58

242.7

1.5G0.3 (phys)

6.1G1.4

Scattering

1997FUH/HUL

TDS

1970GER/RHO

Ni(100, surf.)K–K

Ni(110, surf.)–K

(2) 1986ALB

59.0G2.3

247.0G9.6

62.7G2.3

262.4G9.6

Ni–Y

67.86G0.1

283.9G0.1

Spectrometry

1994ARR/BLU

Ni–Zr

66.9G0.1

279.8G0.1

Spectrometry

1994ARR/BLU

Ni–V

49.3G0.1

206.3G0.2

Spectrometry

1990SPA/MOR

Ni–Nb

65.0G0.01

271.9G0.1

Spectrometry

1994ARR/BLU

–Cs

(continued)

7366—CHAPTER 20—3/2/2007—11:32—SHANMUGAM—15376—XML MODEL B – pp. 903–966

906

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.1 (continued) BDEs of Ni–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment) Ni–Cu

Ni(100, surf.)–Cu

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 47.4G5

198.3G20.9

(1) MS

(1) 1970KAN/STR

(2) 48.9G5.8

204.6G24.3

(2) Review

(2) 1986MOR

(3) 48.2G2.3

201.7G9.6

(3) Spectrometry

(3) 1989FU/MOR

(1) 8.1G0.5

33.8G1.9

(1) STM

(1) 1996MUL/NED

(2) 9.5G1.6

39.6G6.8

(2) LEED

(2) 1998BRU

Ni(surf.)–Ag

36.9G6.9

154.4G28.9

Dadio

1963GOE/PEA

Ni(polycs. surf.)–Ag

24 (phys)

100

FIM

1970OIN/GRE

Ni(polycs. surf.)–Ag

98

410

Review

1995SEE/ALL

Ni–Au

(1) 58.8G7

246G29

(1) Review

(1) 1986MOR

(2) 59.0G3.9

247G16.4

(2) Spectroscopy

(2) 1992SPA/MOR

Ni–Al

53.7G1.2

224.7G4.8

Spectrometry

1993BEH/ARR

Ni(110, surf.)–He

0.1

0.4

HAS

1983GAR/BAR

ONi(100, surf.)–He

(1) 0.18

0.76

HAS

(1) 1979CAN/TAT

(2) 0.18

0.76

w5.2

w21.7

Ni(100, surf.)–Xe

Ni(111, surf.)–Xe

(2) 1998WHI/SEN

TPS

1982CHR/DEM(b)

(1) 7

29.3

(1) PE

(1) 1983DOL/ALN

(2) 4.4G0.2

18.4G0.8

(2) LOD

(2) 1996WON/ZHU

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BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

Ni–H

Ni–D

Ni(polycs. surf.)–H

Ni(polycs. surf.)–H

Ni(100, surf.)–H

Ni(100, surf.)–D

Ni(100, surf.)–H

Ni(110, surf.)–H

Ni(110, surf.)–H

Ni(111, surf.)–H

907

(1) 59.4G2

248.5

(1) MS

(1) 1979KAN/MOO

(2) 60G3

251G13

(2) Review

(2) 1985SQU

(3) 65G6 (4) 59.5G3.7

272G25 248.9G15.4

(3) Ion reactions (4) CID

(3) 1986TOL/BEA (4) 1990FIS/ARM

(5) 57.4G2

240G8

(5) Review

(5) 1996ARM/KIC

%72.4

%302.9

Spectroscopy

(6) 1979HUB/HER

(1) 7G1 (phys)

29G4

(1) FEM

(1) 1957WOR/GOM

(2) 2.9

12.1

(2) H2-conversion

(2) 1968VOL/JUN

46G4

192G17

FEM

1970WOR/GOM

(1) 1985GEO/SAN

(1) 4.0G0.5 (phys) 16.7G2.1

(1) LITD

(2) 3.5

14.6

(2) LITD

(2) 1987MUL/ROO

(3) 3.2

13.4

(3) LITD

(3) 1991LIN/GOM

(4) 3.5

14.6

(4) LOD

(4) 1992LEE/ZHU

(5) 3.8

15.9

(5) LLD

(5) 1992ZHU/LEE

(1) 4.4 (phys) (2) 3.6

18.4 15.1

(1) LITD (2) LITD

(1) 1987MUL/ROO (2) 1991LIN/GOM

(3) 5.0

20.9

(3) LOD

(3) 1992LEE/ZHU

(1) 63

263.6

(1) TPD

(1) 1974CHR/SCH

(2) 64

268

(2) Review

(2) 1991BEN

(1) 5.2 (phys)

21.8

(1) H2-conversion

(1) 1968VOL/JUN

(2) 1.4

5.8

(2) STM

(2) 1998NAB/ZHU

(1) 61.7–62.6

258–262

(1) TPD

(1) 1984PEN/CHR

(2) 64

268

(2) Review

(2) 1991BEN

(1) 3.0 (phys)

12.6

(1) H2-conversion

(1) 1968VOL/JUN

(2) w3

w12.6

(2) LITD

(2) 1991LIN/GOM

(continued)

7366—CHAPTER 20—3/2/2007—11:32—SHANMUGAM—15376—XML MODEL B – pp. 903–966

908

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.1 (continued) BDEs of Ni–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment)

Ni(111, surf.)–D

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(3) 3.4

14.2

(3) SHD

(3) 1993LEE/ZHU

(4) 4.5

18.9

(4) LOD

(4) 1997CAO/NAB

(1) w3.4 (phys)

w14.2

(1) LITD

(1) 1991LIN/GOM

(2) 3.8

15.9

(2) SHD

(2) 1993LEE/ZHU

(3) 5.0

21.0

(3) LOD

(3) 1997CAO/NAB

Ni(111, surf.)–H

62

259

Review

1991BEN

Ni–F

102.4G4.6

428.4G19.3

Spectroscopy

1990DEV/MCQ

(1) 90.1G1.6

377.0G6.7

(1) MS

(1) 1995HIL

(2) 88.3

369.4

(2) Derived from

(2) 1996NIST

Ni(Cl)x–Cl xZ0

DfH0 in ref. 1

(2) 90.2

377.3

Ni–Br

86G3

360G13

Ni–I

70G5

293G21

Ni–O

Review

1968GAY

(1) 91.1G3.9

381G16.4

(1) Spectrometry

(1) 1989MER

(2) 60.0G4.6

251G19

(2) CID

(2) 1990FIS/ARM

(3) 87.5G7.2

366G30

(3) HT MS

(3) 1993WAT/THI

Ni(100, surf.)–O

(1) 124.3 (2) 120.8

520 505.4

(1) Calorimetry (2) Review

(1) 1998BRO/KOS (2) 2003ZEI

Ni(110, surf.)–O

(1) 115.9

485

(2) 124.2

519.7

Review

1991BEN

Ni(100, p2!2, surf.)–O

105

439

Ni(100, c2!2, surf.)–O

101

422

7366—CHAPTER 20—3/2/2007—11:32—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

Ni(111, surf.)–O

Ni–S

909

(1) 112.1

469

(2) 112.3

470

Review

(2) 1998BRO/KOS

(1) 1991BEN

(3) 115.0

481.1

(3) 2003ZEI

(1) 82.3

344.3

(1) MS

(1) 1967DRO/PAT

(2) 85G5

356G21

(2) Review

(2) 1974GUR/KAR

Ni(polycs. surf.)–S

15–28 (phys)

63–117

FEM

1983BLA/BLA

Ni(110, surf.)–S

112

469

Review

1982BAR/AGR

Ni(111, surf.)–S

6.7–6.9 (phys)

28–29

FIM

1985KEL

Ni(111, surf.)–S

(1) 112

469

Review

(1) 1982BAR/AGR

(2) 85

356

Ni(powder)–S

34.3G4.3

143.5G18.0

g-Al2O/Ni –S

34.2G3.9

143.1G16.3

Ni(100, surf.)–N

141.8

Ni(110, surf.)–N

(2) 1995SEE/ALL

Equilibrium

1980MCC/WIS

593.3

Review

2003ZEI

(1) 137

573

Review

(1) 1991BEN

(2) 145.8

610

(1) 138

577

(2) 135

565

(1) R78.0

R326.4

(2) 80.5

337.0

Ni(polycs. surf.)–C

6.9 (phys)

28.9

Ni(polycs. surf.)–C

(1) 173 (2) 170

Ni(111, surf.)–N

Ni–C

(2) 2003ZEI

Spectrometry

(1) 2002BRU/MOR (2) 2006RAO/RED

Review

1995SEE/ALL

724

(1) AES

(1) 1974SHE/PAT

711

(2) Review

(2) 1995SEE/ALL

(continued)

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

910

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.1 (continued) BDEs of Ni–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds fragment)

Methods

reference in parentheses)

(boldfaceZdissociated

kcal/mol

(reference in

kJ/mol

parentheses)

References

Ni(110, surf.)–C

45.7

191

Adsorption

1999BRO/KOS

Review

1991BEN

Ni(100, p(2!2, surf.)–C

169

707

Ni(111, p(2!2, surf.)–C

160

669

Ni–Si

76.0G4.1

318G17

MS

1969MAH/MCL

MS

(1) 1968KAN/STR

Ni–Ge

(1) 63G5

264G21

(2) 66.4G2.9

278G12

(2) 1985GIN/SHI

(3) 69.4G2.6

290.3G10.9

(3) 1988SHI/KIN

Ni(foil)–H2

7–10 (phys)

29–42

TDS

1990CAB

Ni(foil)–H2

28–30

117–126

TDS

1990CAB

Ni(polycr. surf.)–H2

(1) 29

121

Calorimetry

(2) 25.3

106

(1) 1958KLE/STO (2) 1964BRE/HAY

(3) 18

75

(3) 1966BRO/WED

(4) 27.4

114.5

(4) 1967LAP

(5) 18

75

(5) 1972WED/FIS

Ni(polycr. surf.)–D2

19.1

80

Calorimetry

1971WED/BRO

Ni(100, surf.)–H2

(1) 23.1

97

(1) TDS

(1) 1973LAP/NEI

(2) 23

96

(2) LEED/FDS

(2) 1974CHR/SCH

(3) 22

92

(3) TPRS

(3) 1979KO/MAD

(4) 21.3G1

89.1G4

(4) TPD

(4) 1981JOH/MAD

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

911

Ni(100, 2!2, surf.)S–H2

17.4G2

72.8G8.4

TPD

1981JOH/MAD

Ni(110, surf.)–H2

(1) 19.5 (a-state) (1) 29.5 (b-state)

82 123

(1) TDS

(1) 1971ERT/KUE

(2) 22.3

93.3

(2) FD MS

(2) 1973MCC/FAL

(3) 20.3

85

(3) TDS

(3) 1973LAP/NEI(b)

(4) 21.5

90

(4) LEED/FDS

(4) 1974CHR/SCH

(5) 21.5

90

(5) Review

(5) 1978MAD/BEN

(1) 22.7

95

(1) TDS

(1) 1972LAP/NEI(b)

(2) 23

96

(2) LEED/FDS

(2) 1974CHR/SCH

Ni(polycr. surf.)–D2

19.1

80

Calorimetry

1971WED/BRO

Ni(100, surf.)–D2

4.2 (phys)

17.6

LITD

1986MUL/ROO

Ni(111, surf.)–D2

21.3

89.1

TPD

1987MIL/SID

Ni(111, surf.)–Cl2

75.5

316

TDS

1980ERL

Ni–O2

w57

w239

Kinetics

1992MIT

Ni(polycr. surf.)–O2

(1) 107

448

(1) Calorimetry

(1) 1965BRE/HAY

(2) w150

w627

(2) Calorimetry

(2) 1958KLE/STO

(3) 115

481

(3) Calorimetry

(3) 1960BRE/HAY

(4) 89

372

(4) Calorimetry

(4) 1960WED

(5) 107

448

(5) Review

(5) 1982RAO/KAM

Calorimetry

Ni(111, surf.)–H2

Ni(100, surf.)–O2

(1) 128.1

536

(2) 131.5G1.8

550G7.5

Ni(110, surf.)–O2

(2) 113.5G2.6

475G11

Ni(111, surf.)–O2

(2) 105.2G4.5

440G19

Ni(211, surf.)–O2

(3) 148.2

620

NiO(polycr. surf.)–O2

54

226

(1) 1996VAT/YEO (2) 1997STU/WAR

(3) 2004KAR/FIO

Review

1964HAY/TRA

(continued)

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

912

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.1 (continued) BDEs of Ni–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

Methods

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

(reference in

kJ/mol

parentheses)

References

Ni(111, surf.)–OH

87

364

Adsorption

1989YAN/WHI

Ni(CO)3–N2

w10

w42

Kinetics

1983TUR/SIM

Ni(polycr. surf.)–N2

w10

w42

Calorimetry

1950BEE/COL

Ni(100, surf.)–N2

0.16 (phys)

0.66

HAS

1996BER/STE

Ni(100, surf.)–N2

6–10

25–42

TD

1968KIN

Ni(110, surf.)–N2

0.13 (phys)

0.55

HAS

1996BER/STE

Ni(110, surf.)–N2

(1) 8.5

35.5

TD

(1) 1979GRU/DRI

(2) w8.6

w36

(2) 1980GOL/GRU

(3) 9.6G0.4

40G1.5

(3) 1986GOL/GRU

(1) w7 (2) 8.4

w29 35.1

(1) TD (2) IRAS

(1) 1968KIN (2) 1991YOS/ZEN

FTR

1998PAR/NIE

Ni(111, surf.)–N2

Nix–N2 xZ19

18.3G0.4

76.8G1.6

20

19.0G0.4

79.3G1.5

21

20.1G0.4

84.0G1.6

22

19.9G0.4

83.1G1.6

23 24

19.5G0.4 19.6G0.6

81.6G1.8 81.9G2.4

25

20.2G0.3

84.4G1.2

26

19.3G0.3

80.6G1.3

27

19.4G0.5

81.3G2.1

28

17.8G0.4

74.5G1.6

29

17.8G0.3

74.5G1.3

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

30

17.9G0.4

74.7G1.6

31

18.4G0.5

76.8G1.9

32 33

19.0G0.3 18.4G0.4

79.4G1.4 77.1G1.5

34

17.4G0.4

72.9G1.7

35

19.1G0.3

79.8G1.4

36

18.8G0.5

78.8G1.9

37

17.1G0.3

71.7G1.4

38

16.2G0.3

67.9G1.1

39

16.1G0.2

67.2G1.0

40 41

16.3G0.3 17.7G0.5

68.0G1.1 74.2G1.9

42

17.0G0.3

71.0G1.2

43

17.4G0.4

73.0G1.6

44

17.4G0.3

72.7G1.1

45

16.7G0.2

70.0G1.0

46

17.2G0.3

71.8G1.3

47

17.7G0.3

74.0G1.1

48 49

17.4G0.3 17.4G0.2

72.9G1.3 72.9G0.9

50

16.8G0.3

70.4G1.3

51

16.9G0.3

70.9G1.3

52

16.9G0.3

70.8G1.3

53

17.5G0.3

73.1G1.2

54

17.2G0.4

71.9G1.8

55

17.1G0.4

71.4G1.6

56 57

16.8G0.5 16.3G0.4

70.3G1.9 68.1G1.5

58

17.4G0.3

72.6G1.1

59

17.4G0.5

72.8G2.2

60

17.0G0.3

71.2G1.1

61

17.3G0.5

72.2G2.0

62

17.2G0.5

71.9G2.0

63

17.4G0.5

72.6G1.9

64 65

17.9G0.8 17.4G0.7

75.0G3.2 73.0G2.8

66

17.8G0.5

74.4G2.0

67

17.3G0.5

72.4G2.2

68

18.3G0.5

76.4G1.9

69

17.9G0.5

74.8G2.0

70

17.6G0.7

73.5G2.9

71

16.7G0.7

70.0G2.9

23

96

Ni(100, surf.)–NO

Ni(100, surf.)–NO

913

TPD

1980PRI/BAK

(1) 101.8

426

(1) Calorimetry

(1) 1996VAT/YEO

(2) 92.0

385

(2) Updated

(2) 1998BRO/KOS

(continued)

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

914

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.1 (continued) BDEs of Ni–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ni(111, surf.)–NO

25

105

TDS

1975CON/ERT

Ni(211, surf.)–NO

38.2

160

Calorimetry

2003KAR/FIO

NiO(100, surf.)–NO

(1) 12.0

50.2

TDS

(1) 1991KUH/ODO

(2) 13.1

55.0

Ni(CO)x–CO xZ0

1 2 3

Ni(polycr. surf.)–CO

(2) 2000FRE

(1) 29G15

121G63

(1) PES

(2) 25.8

107.9

(2) CL

(1) 1982STE/FEI (2) 1988MCQ/MOR

(3) 40.5G5.8

169.5G24.3

(3) CID

(3) 1992SUN/WAN

(1) 54G15

226G63

(3) 47.1G5.8

197G24

(1) 13G10

54G42

(3) 28.3G2.3

118.4G9.6

(1) 25G2 (4) 21.5G0.4

104.6G8.4 90.0G1.7

(4) Kinetics

(4) 1968DAY/BAS

Calorimetry

(1) 1950BEE

(1) 35

146

(2) w33

w138

(2) 1958KLE/STO

(3) 42

176

(3) 1965BRE/HAY

(4) 30

125

(4) 1974WED/PAP

Ni(foil)–CO

6–10 (phys)

25–42

TDS

1990CAB

Ni(foil)–CO

30–36

126–151

TDS

1990CAB

Ni(100, surf.)–CO

(1) 5.0 (phys)

21

(1) LITD

(1) 1986MUL/ROO

(2) 6.4

26.8

(2) LITD

(2) 1987ROO/COS

(3) 0.6–0.8

2.6–3.2

(3) HAS

(3) 1996HOF/TOE

(4) 1.4

5.8

(4) HAS

(4) 2003GRA

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

Ni(100, surf.)–CO

915

(1) 29.4

123

(1) Calorimetry

(1) 1993STU/ALS

(2) 29.2G1

122G4

(2) TDS

(2) 1993ALS/STU

(3) 30.4 (4) 32.3G1.2

127 135G5

(3) TDS (4) TPD

(3) 1994TAK/YOS (4) 1996MUS/MAD

(5) 29.2

122

(5) Calorimetry,

(5) 2000GE/KOS

updated

Ni(100, 2!2, surf.)S–CO

26.1G1

109.2G8.4

Ni(110, surf.)–CO

(1) 3.9

16.4

(1) TD

(1) 1967DEG(b)

(2) 2.8–4.0 (phys) (3) 0.8–1.3

11.7–16.7 3.4–5.5

(2) LOD (3) HAS

(2) 1993XIA/XIE (3) 1996HOF/TOE

(4) 2–3

8–13

(4) LOD

(4) 1997XIA/XIE

HAS

1996BER/HOF

parallel to !110O

1.31G0.09 (phys)

5.50G0.39

perpendicular to !001O

0.81G0.09

3.38G0.39

Ni(110, surf.)–CO

(1) 32.5 (2) 30.6

136 128

(1) HR–LEED (2) Kinetics

(1) 1987BAU/HOC (2) 1990FEI/DES

(3) 25–32

105–134

(3) Calorimetry

(3) 1993STU/ALS

(4) 31.8

133

(4) Equilibrium

(4) 1994TAK/YOS

(5) 31.1

130

(5) Calorimetry,

(5) 2000GE/KOS

Ni(110, surf.)–CO

TPD

1981JOH/MAD

updated

Ni(111, surf.)–CO

Ni(111, surf.)–CO

(1) 6.9 (phys)

28.9

(1) Diffraction

(1) 1988ZHU/RAS

(2) 6.8

28.5

(2) FEM

(2) 1990LIN/LU

(1) 25.8

108

(1) TDS

(1) 1986FRO/KOH

(2) 29.1

122

(2) TPD

(2) 1987MIL/SID

(3) 26

109

(3) Calorimetry

(3) 1993STU/ALS

(4) 31.1

130

(4) Equilibrium

(4) 1994TAK/YOS

(5) 30.1

126

(5) Calorimetry,

(5) 2000GE/KOS

updated

Ni(211, surf.)–CO

33.2

139

Calorimetry

2003KAR/FIO(b)

Ni(511, surf.)–CO

6.4 (phys)

26.8

FEM

1990LIN/LU

(continued)

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

916

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.1 (continued) BDEs of Ni–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ni(511, surf.)–CO

28.5

119

Review

1995SEE/ALL

Ni(14 13 13, surf.)–CO

28.4

119

TPD

2004BJO/CHE

(1) 1994VES/XU

NiO(100, surf.)–CO

(1) 10.4G2

43.5G8

(1) IR

(2) 7.0–8.8

29–37

(2) TDS

(2) 1995CAP/KLI

(3) 6.9

28.9

(3) TDS

(3) 1999WIC/ROD(b)

Ni(100, surf.)/H2–CO

15.7

65.7

TPD

1983KOE/PEE

Ni(110, surf.)CO–CO

1.8 (phys)

7.4

Diffraction

1993XIA/XIE

Ni(polycr. surf.)–CO2

(1) 44

184

(1) Review

(1) 1964HAY/TRA

(2) 54

226

(2) Calorimetry

(2) 1965BRE/HAY

NiO(polycr. surf.)–CO2

28

117

Review

1964HAY/TRA

Ni(110, surf.)–CH

45.7

191

TPD

1999BRO/KOS

45.7

191

Ni–H2O

w7

w29

Kinetics

1994MIT/BLI(b)

Ni(111, surf.)–H2O

(1) 10

42

TPD

(1) 1982MAD/NET

(2) 11.5G0.5

48.1G2.1

12.4G0.7

52G3

–CH2

Ni(111, surf.)/K–H2O

(2) 1985STU/THI

Equilibrium

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

1994KUC/SCH

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

Al2O3/NiAl

917

10.7

44.8

TPD

2006OZE/PED

Ni(100, surf.)–H2S

39.2

164

Review

1982BAR/AGE

NiO(polycr. surf.)–ON2

46

192

Review

1964HAY/TRA

Al2O3/NiAl

8.7

36.6

TPD

2006OZE/PED

Ni(polycr. surf.)–NH3

37.0

155

Calorimetry

1953WAH/KEM

Ni(110, surf.)–NH3

20

84

TDS

1985KLA/ALV

Ni(111, surf.)–NH3

(1) 21.0

87.9

(1) Combined

(1) 1983RED/ZEI

(2) 17

71

(2) ESDIAD

(2) 1987DRE/LAN

NiO(100, surf.)–NH3

w30

w126

TPD

1993WU/TRU

Ni–CH3

(1) 55G3 (2) 49.7G2

230G13 208G8

(1) GIB MS (2) Review

(1) 1989GEO/FIS (2) 1996ARM/KIC

Ni(100, surf.)–CH3

3.1G0.4 (phys)

13.0G1.7

SIMS

1987ZHO/WHI

Ni(100, surf.)–CH3

%34

%142

TPD, revised

1992TJA/ZAE

Ni(polycs. surf.)–CH4

11

46

Review

1964HAY/TRA

(111, surf.)–H2O

(111, surf.)–ON2

Ni(111, surf.)–CH4

(1) 2.7

11.4

(1) Re-cal.

(1) 1993SZU/LEV

(2) 3.0

12.5

(2) Mol. beam

(2) 2004KAO/MAD

(continued)

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

918

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.1 (continued) BDEs of Ni–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Ni(100, surf.)–C2H6

9.6

40.2

–C3H8

3.8

15.9

–nC4H10

3.1

13.0

Ni(111, surf.)–C2H6– –C3H8 –nC4H10

5.1 7.2 8.8

Ni(100, surf.)–CH3OH

Methods (reference in parentheses)

References

TPD

1988SAU/GOO

21.3 30 37

Mol. beam

2004KAO/MAD

14.0

58.6

LID

1987HAL

Ni(100, surf.) –HCO(O)D

25.5

106.7

Decomposition

1979BEN/MAD

Ni–C2H2

46G6

193G25

Kinetics

1994MIT/BLI

Ni(100, surf.)–C2H2

63.1

264

Calorimetry

2000VAT/YEO

Ni(110, surf.)–C2H2

45.4

190

Calorimetry

1999BRO/KOS

Ni–C2H4

35.2G4.2

147.3G17.6

Fluorescence

1994MIT

Ni(polycr. surf.)–C2H4

(1) 60

251

(1) Calorimetry

(1) 1950BEE/COL

(2) 58

243

(2) Review

(2) 1964HAY/TRA

Ni(100, surf.)–C2H4

w12 (phys)

w48

TPD

1993TJA/ZAE

Ni(100, surf.)–C2H4

48.5

203

Calorimetry

2000VAT/YEO

Ni(110, surf.)–C2H4

10.8–12.9 (phys)

45–54

AES/MS

1977ZUH/HUD

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

919

Ni(110, surf.)–C2H4

28.7

120

Calorimetry

1999BRO/KOS

Ni(100, surf.)–C3H7I –C4H9I

9.8 11.0

41.0 46.0

TPD

1995TJA/FRA

–C5H11I

11.0

46.0

–C6H13I

11.6

48.5

TPD

2001ZAE

Ni(100, surf.)–CH3

13.5

56.5

–C2H5

9.3

38.9

–s-C4H9

12.3

51.5

–t-C4H9 –n-C5H11

10.5 11.1

43.9 46.4

–neo-C5H11

11.1

46.4

–n-C6H13

11.7

49.0

20–30

84–125

Derived

2001PAN/RAO

Kinetics

1994MIT/BLI

FT–IR

(1) 2005DOR/STE

Ni–C6H6

Ni–propyne

37G5

155G21

–2-butyne

29G5

121G21

(CO)2Ni–(N-heterocyclic carbenes)

R N

N

R

RZ2,4,6-trimethylphenyl

(1) 46.5

194.6

2,6-diisopropylphenyl

(1) 45.4

190.0

t-butyl

(1) 44.3 (2) 39G3

185.4 163.2G12.6

cyclohexyl

(1) 46.3

193.7

adamantyl

(1) 46.5

194.6

(2) 43G3

179.9G12.6

(2) 2003DOR/STE

(CO)2Ni–(N-heterocyclic carbenes) .. R N N

R

RZ2,4,6-trimethylphenyl

47.2

197.5

2,6-diisopropylphenyl

46.1

192.9

t-butyl

45.1

188.7

FT–IR

2005DOR/STE

(continued)

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

920

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.1 (continued) BDEs of Ni–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ni(CO)2–L 25.7

107.5

PPh3

30.0

125.5

P(tBu)3

34.3

143.5

RZ2,4,6-trimethylphenyl

40.2

168.2

2,6-diisopropylphenyl

38.0

159.0

t-butyl

21.8

91.2

RZ2,4,6-trimethylphenyl

41.1

172.0

2,6-diisopropylphenyl

38.5

161.1

t-butyl

24.0

100.4

cyclohexyl

39.6

165.7

adamantyl

20.4

85.4

LZPH3

FT–IR

2005DOR/STE

FT–IR

2005DOR/STE

FT–IR

2005DOR/STE

FT–IR

2005DOR/STE

(CO)3Ni–(N-heterocyclic carbenes)

R N

N

R

(CO)3Ni–(N-heterocyclic carbenes) .. R N N

R

Ni(CO)3–L LZPH3

22.7

95.0

PPh3

26.7

111.7

P(tBu)3

28.0

117.2

(cod)Ni–(cod)

50.0

209.2

Review

1994NOL

9.0

37.7

Equilibrium

1983BAE/FED

codZ1, 5-cyclo-ctadiene

(CO)4Ni–Fe(CO)5

7366—CHAPTER 20—3/2/2007—11:33—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

921

20.1.2 NiC– and NiK–X bonds Table 20.1.2 BDEs of NiD– and NiL–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) NiC–Ni

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 48.0G1.6

200.8G6.7

(1) CID

(1) 1991LIA/SU

(2) 54.4G0.5 (3) 52.7G0.6

227.6G1.9 220.3G2.4

(2) R2PI (3) Spectrometry

(2) 1994ASH/BEL(d) (3) 1995PIN/LAN

(4) 49.8

208

(4) CID

(4) 1996ARM/KIC

(1) CID

(1) 1996ARM/KIC

NiC(Ni)x–Ni xZ1

(1) 56.2

235

2

(1) 47.6

199

3

(1) 53.3

223

4 5

(1) 65.7 (1) 70.7

275 296

6

(1) 63.3

265

7

(1) 67.6

283

8

(1) 67.6

283

9

(1) 70.0

293

10

(1) 80.1

335

11

(1) 84.1

352

12 13

(1) 71.5 (1) 79.8

299 334

14

(1) 80.8

338

15

(1) 84.6

354

16

(1) 81.5

341

N

(2) 102.4

428

(2) Review

(2) 1994ARM/HAL

(3) w88.4

w370

(3) Extrapolate

(3) This volume

(1) 64G5 (2) !68G5

268G21 !285G21

(1) PD (2) Ion reactions

1987HET/FRE

xZ0

2.97G0.1

12.4G0.4

Equilibrium

1991KEM/HSU

1

3.42G0.1

14.3G0.4

2

1.34G0.1

5.6G0.4

2.37G0.1

9.9G0.4

Equilibrium

1991KEM/HSU

2.16G0.1

9.0G0.4

NiC–Fe

NiC(He)x–He

NiC(Ne)x–Ne xZ0 1

(continued)

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

922

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.2 (continued) BDEs of NiC– and NiK–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) NiC–Ar

NiC 2 –Ar

NiC–H

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 13.6

56.8

(1) PD

(1) 1988LES/BRU

(2) 13.96G0.01

58.41G0.06

(2) PD

(2) 1994ASH/BEL

(3) 12.9

53.9

(3) GDMS

(3) 1995BAR/SMI

69.2

289

PD

1988LES/BRU(b)

Ion reactions

(1)!71

!297

(2) 42.9G2.1 (3) 39.7G1.8

179.5G8.7 166G8

(2) 1980ARM/BEA(b) (3) 1986ELK/ARM

(1) 1979ALL/RID

(4) 37.8G1.8

158.1G7.7

(4) 2005LIU/ZHA

NiC(Ni)x–D xZ0

(1) 39.7G1.8

166.0G7.7

1

(1) 70.1G2.3

293.3G9.6

(2) 66.4G2.1

277.9G8.7

2

(1) 46.1G2.3 (2) 39.4G3.2

193.0G9.6 165.0G13.5

3 4 5 6 7 8 9 10 11 12

(1) 44.7G3.7

187.2G15.4

(2) 41.0G2.5

171.7G10.6

(1) 48.2G3.5

201.6G14.5

(2) 48.9G2.8

204.5G11.6

(1) 52.1G4.4

218.1G18.3

(2) 50.7G2.8

212.3G11.6

(1) 51.0G6.5 (2) 49.3G3.0

213.2G27.0 206.5G12.5

(1) 48.4G9.5

202.6G39.6

(2) 47.7G2.1

199.7G8.7

(1) 51.7G7.8

216.1G32.8

(2) 52.1G2.8

218.1G11.6

(1) 55.8G7.6

233.5G31.8

(2) 56.3G3.5

235.4G14.5

(1) 60.6G8.8 (2) 58.3G2.5

253.8G36.7 244.1G10.6

(1) 57.2G8.1

239.3G33.8

(2) 57.9G3.0

242.2G12.5

(1) 60.0G7.8

250.9G32.8

(2) 56.3G3.5

235.4G14.5

Ion reactions

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

(1) 2002LIU/LIY (2) 2004LIU/ZHA

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

13 14 15

(CO)4NiC–H

(h5-C5H5)(L)NiC–H LZNO (h5-C5H5)

NiC–F

(1) 60.9G7.8

254.7G32.8

(2) 58.1G3.2

243.1G13.5

(1) 58.8G8.8 (2) 59.0G3.5

246.0G36.7 247.0G14.5

(1) 61.6G8.5

257.6G35.7

(2) 59.3G3.2

248.0G13.5

923

(1) 62G3

259.4G12.6

(1) Thermochem.

(1) 1981STE/BEA

(2) 59.3G2.2

248G9

(2) Review

(2) 1990SIM/BEA

(1) 78G3

326.4G12.6

(1) Thermochem.

(1) 1981STE/BEA

(2) 75.3G3.3

315G14

(2) Review

(2) 1990SIM/BEA

(1) 54G3

225.9G12.6

(2) 51.4G3.1

215G13

(1) R109

R456

(1) Ion reactions

(1) 1979ALL/RID

–Cl

(2) 45.9G0.9

192G4

(2) CID

(2) 1989FIS/SUN

–Br –I

(1) O69 (1) O71

O289 O297

Equilibrium

1998KEM/WEI(b)

NiC(H2)x–H2 xZ0

17.3G0.3

72.4G1.3

1

17.6G0.3

73.6G1.3

2

11.3G0.3

47.3G1.3

3

7.1G0.3

29.7G1.3

4 5

4.2G0.2 0.8G0.2

17.6G0.8 3.3G0.8

NiC–C

100

418

Spectrometry

2002BRU/MOR

NiC–CH

71.9G2.8

301.0G11.6

GIB MS

2005LIU/ZHA

71.9G2.8

301.0G11.6

Ion reactions

2004LIU/ZHA

111.4G2.8 121.3G3.2

466.0G11.6 507.5G13.5

NiC(Ni)x–CD xZ0 1 2

(continued)

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

924

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.2 (continued) BDEs of NiC– and NiK–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment)

recommended data; reference in parentheses) kcal/mol

kJ/mol

3

117.6G2.8

492.1G11.6

4

118.5G3.5

495.9G14.5

5

116.9G3.9

489.2G16.4

6

113.2G4.6

473.7G19.3

7

121.5G4.8

508.5G20.3

8

122.9G4.6

514.3G19.3

9

131.7G4.8

550.9G20.3

10 11

131.4G4.8 135.1G4.4

550.0G20.3 565.4G18.3

12

137.2G6.2

574.1G26.1

13

139.3G5.8

582.8G24.1

14

138.6G4.8

579.9G20.3

15

140.4G4.8

587.6G20.3

73.1G0.9 87.4G2.0

305.9G3.9 365.7G8.7

Methods (reference in parentheses)

References

NiC(Ni)x–CD2 xZ0 1 2

89.2G1.8

373.4G7.7

3

w83

w347

9

w87.6

w367

10

89.0G1.8

372.4G7.7

11

90.4G2.0

378.2G8.7

12

90.6G2.3

379.2G9.6

13 14

92.2G2.5 93.2G2.3

385.9G10.6 389.8G9.6

15

92.5G2.8

386.9G11.6

NiC–CF2

(1) 47G7

197G29

–CH2

(1) 86G6

360G25

Ion reactions

2004LIU/ZHA

(1) Ion beam

(1) 1983HAL/ARM

(2) 75.2G1.6

314.5G6.8

(2) GIB MS

(2) 1990FIS/ARM

(3) 73.1G1

306G4

(3) Review

(3) 1996AEM/KIC

(4) %70.5G1.2 (5) 73.8G1.8

%295G5 308.7G7.7

(4) PD (5) GIB MS

(4) 2000HUS/AGU (5) 2005LIU/ZHA

NiC(CH3)x–CH3 xZ0

(1) !56

!234

(1) Ion reactions

(1) 1979ALL/RID

(2) 48G5

201G21

(2) Ion beam

(2) 1984MAN/HAL

(3) 44.7G1.4

187G6

(3) GIB MS

(3) 1989GEO/FIS

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

1

925

(4) 40.6G1.6

169.8G6.8

(4) GIB MS

(4) 2005LIU/ZHA

(5) O51.1

O214

(5) Review

(5) 1990SIM/BEA

NiC(CH4)x–CH4 xZ0

(1) 24.9

104.2

(1) Equilibrium

(1) 2001ZHA/KEM(b)

(2) 23.1G1.2

96.5G4.8

(2) GIB MS

(2) 2005LIU/ZHA

1

(1) 26.5

110.9

2

(1) 9.3

38.9

3

(1) w5.5

w23

4

(1) w2.0

w8.4

5 N

(1) w2.0 (3) w2

w8.4 w8

(3) Extrapolate

(3) This volume

(1) O34.8G4.8

145.7G20.3

(1) GIB MS

(1) 1990FIS/ARM

(2) O4.3G4.3

O18.2G18.3

(2) Revised

(2) 1994FIS/ARM

NiC–C2H2

NiC–CHCH3 –C2H5 –C2H6

(1) 45G2

188G8

(1) IRMPD

(1) 1997SUR/RAN

(2) 53G6

222G25

(2) GIB MS

(2) 1989GEO/FIS

(2) 53.1G5.8 (2) 28G5

222G24 117G21

(3) 28.7G3

120.1G12.6

(3) KERD

(3) 1995CAR/KOP

(1) 44G5

184G21

(1) Ion reactions

(1) 1988HAN/BEA

(2) O34.8G4.8

O146G20

(2) Ion reactions

(2) 1990FIS/ARM

(3) 43.6G2.5

182G11

(3) Ion reactions

(3) 1998SIE/JAR

(4) 42 (3) 41.3G3.3

175.7 173G14

(4) Review

(4) 1998SCH/SCH

TRPD

1995LIN/DUN

NiC(C2H4)x–C2H4 xZ0

1

NiC(h5-C5H5)x–(h5-C5H5) xZ0

91.3G1.7

382G7

1

74.8G1.7

313G7

NiC(C6H6)x–C6H6 xZ0

(1) 58.1G2.6

243G11

(1) CID

(1) 2000ROD/ARM(b)

Rw182 147G12

(2) PD

(2) 2005JAE/DUN

1

(2) Rw43.6 (2) 35.1G2.9

NiC–O

(1) 45.9G2.3

192G10

CID

(1) 1982ARM/HAL

(2) 66.0G1.8

275.9G7.7

(2) 1990FIS/ARM

(continued)

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

926

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.2 (continued) BDEs of NiC– and NiK–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NiC(Ni)x–O xZ1 2

109.3G0.7

457.3G2.9

97.5G3.2

408.1G13.5

3

75.9G1.4

317.4G5.8

4

68.9G2.3

288.5G9.6

5

68.0G1.2

284.6G4.8

6

56.7G2.3

237.3G9.6

7 8

57.2G0.5 71.3G2.5

239.3G1.9 298.1G10.6

9

72.6G0.7

303.9G2.9

10

63.0G2.8

263.4G11.6

11

77.3G1.6

323.2G6.8

12

66.9G1.2

279.8G4.8

13

83.2G0.5

348.3G1.9

14

78.9G0.9

330.0G3.9

15 16

66.2G0.9 71.9G1.6

276.9G3.9 301.0G6.8

17

69.4G1.8

290.4G7.7

NiC(Ni)x–2O xZ2

183.1G7.8

766G33

3

200.4G8.1

838G34

4

211.5G6.7

885G28

5

211.0G7.4

883G31

6

210.1G8.3

879G35

7

220.5G8.3

922G35

8

213.5G9.0

893G38

9 10

204.5G9.0 216.5G9.5

856G38 906G40

11

213.8G9.5

894G40

12

210.1G9.2

879G39

13

204.8G9.7

857G41

14

200.2G10.1

837G42

15

190.7G10.1

798G42

NiC(H2O)x–OH xZ0

1

GIB MS

2003VAR/LIY

Review

2003VAR/LIY

(1) !91

!381

(1) Ion reactions

(1) 1979ALL/RID

(2) 42.2

177

(2) CID

(2) 1989MAG/DAV(b)

(3) 56.2G4.5

235G19

(3) Review

(3) 1996ARM/KIC

(4) %64.8G2.2 (5) 36.6

%271G9 153

(4) PD (5) ES MS

(4) 2000THO/AGU (5) 2000VUK/STO

(4) 79.8G1.2

%334G5

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

927

NiC(CO)x–CO xZ0

1 2 3

(1) 38G5

159G21

(1) KERD

(1) 1988HAN/BEA

(2) 42.4G2.5 (3) 41.8G2.5

177.5G10.6 175G11

(2) CID (3) CID, revised

(2) 1995KHA/STE (3) 2000ROD/ARM

(2) 40.4G2.5

168.8G10.6

(3) 40.2G2.5

168G11

(2) 22.6G1.4

94.6G6.8

(3) 22.0G1.4

92G6

(2) 18.4G0.7

77.2G2.9

(3) 17.2G0.7

72G3

NiC–CO2

24.9G0.2

104G1

PD

1994ASH/BEL(b)

NiC(OH)–H2O

%64.8G2.2

%271G9

PD

2000THO/AGU

(1) 36.5

152.7

(1) CID

(1) 1989MAG/DAV(b)

(2) 39.7

166.1

(2) CID

(2) 1989MAR/SQU

(3) 43.9G0.8 (1) 38.0

183.7G3.3 159.0

(3) CID

(3) 1994DAL/HON

(2) 40.6

169.9

NiC(H2O)x–H2O xZ0

1

(3) 40.2G1.8

168.2G7.5

(3) 16.2G1.5

67.8G6.3

3

(3) 12.3G1.5

51.5G6.3

N

(4) w10.5

w44

(4) Extrapolate

(4) This volume

43.1

180.3

Derived

1984STO/SPL

2

NiC(h5-C5H5)–H2O

NiC(h5-C5H5)–CH3OH –CH3SH

NiC(h5-C5H5)–C2H5OH

(1) 46.3

193.7

(1) Derived

(1) 1984STO/SPL

(2) 45.6

190.8

(2) Correction

(2) 1990SIM/BEA

(2) 47.1

197.1

Correction

1990SIM/BEA

Correction

1990SIM/BEA

47.5

198.7

–i-PrOH

49.5

207.1

–t-BuOH

50.8

212.5

NiC(h5-C5H5)–MeCHO

47.0

196.7

–EtCHO

48.1

201.3

–C2H3CHO

49.3

206.3

–t-BuCHO

49.6

207.5

(continued)

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

928

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.2 (continued) BDEs of NiC– and NiK–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

kJ/mol

NiC(h5-C5H5)–MeOMe

46.9

196.2

–MeOAc

50.9

213.0

–EtOEt

50.9

213.0

–MeSMe

51.1

213.8

NiC(h5-C5H5)–MeC(O)Me

Methods (reference in parentheses)

References

Correction

1990SIM/BEA

(1) 51.4

215.1

(1) Derived

(1) 1984STO/SPL

(2) 50.7

212.1

(2) Correction

(2) 1990SIM/BEA

–MeC(O)OMe (1) 51.6

215.9

FT–ICR

2004GRI/MAN

NiC–furan

59

NiC–S

(1) 60G5

251G21

(1) PD

(1) 1986JAC/FRE

(2) 57.8G1

242G4

(2) PD

(2) 2001HUS/AGU

(3) 57.6G0.9

241.0G3.9

(3) CID

(3) 2002RUE/ARM

(3) 56.0G2.3

234.5G9.6

xZ0

26.5G2.5

110.9G10.5

CID

1995KHA/STE

1

26.5G2.5

110.9G10.5

–CS

247

NiC(N2)x–N2

2

13.4G0.9

56.1G3.8

3

10.1G2.3

42.3G9.6

NiC(NO)x–NO xZ0

(1) 43G5

180G21

(1) Ion reactions

(1) 1985CAS/FRE

227.6G7.5 122.6G6.7

(2) CID

(2) 1995KHA/STE

1

(2) 54.4G1.8 (2) 29.3G1.6

2

(2) 27.4G1.2

114.6G5.0

NiC(h5-C5H5)–NO –HCN

NiC–N2O

(1) %43G3

%180G12.6

(1) PD

(1) 1979BUR/FRE

(2) 45.9

192.0

(2) Correction

(2) 1990SIM/BEA

(2) 47.6

199.2

25.3G0.1

105.8G0.3

PD

1995BEL/BUT

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

NiC–NH2

55.6G1.8

NiC(NH3)x–NH3 xZ0 1

232.5G7.7

GIB MS

CID

(1) 51.2

214.2

(2) 56.9G4.5

238G19

(1) 55.1

230.5

(2) 60.0G2.9

251G12

2

(1) 17.8

74.5

(2) 22.2G1.9

93G8

3

(2) 8.4G1.4

35G6

NiC(h5-C5H5)–NH3 –PH3

NiC(h5-C5H5)–MeCN –MeNC

NiC(h5-C5H5)–MeNH2

929

1991CLE/ARM

(1) 1989MAR/SQU (2) 1998WAL/ARM

(1) 53.0

221.8

(1) Derived

(1) 1984STO/SPL

(2) 52.3

218.8

(2) Correction

(2) 1990SIM/BEA

(2) 45.5

190.4

(1) 53.9

225.5

(1) Derived

(1) 1984STO/SPL

(2) 53.2

222.6

(2) Correction

(2) 1990SIM/BEA

(2) 57.6

241.0

(1) 55.9

233.9

(1) Derived

(1) 1984STO/SPL

(2) 55.2

231.0

(2) Correction

(2) 1990SIM/BEA

(1) 57.5

240.6

(2) 56.8

237.7

(1) 57.1

238.9

(2) 56.4

236.0

–PMe3

(2) 57.6

241.0

–AsMe3

(2) 57.2

239.3

61.3G3.6

256.5G15.2

CID

2000ROD/STA

58.8G2.3

245.9G9.6

xZ0

O68

O285

1

47.0

196.6

NiC–adenine

72.0G2.4

NiC–imidazole

67.8G2.2

–Me2NH –NMe3

NiC–pyridine –pyrimidine

2001AMU/ROD

NiC(L)x–L, LZpyrrole Kinetics

2000GAP/YAN

301.3G10.1

CID

2002ROD/ARM

283.8G9.4

CID

2004RAN/AMU

(continued)

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

930

Comprehensive Handbook of Chemical Bond Energies

Table 20.1.2 (continued) BDEs of NiC– and NiK–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) NiC–Si

recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 77.9G1.6

326G6.7

–SiH

(2) 77.9G3.5

326G15

–SiH2

(2) R55.1G1.6

R230.5G6.7

(3) 67G6

280G25

–SiH3

(2) 44.0G2.8

184.1G11.7

NiC–SiH(CH3) –Si(CH3)2

O60

O251

O69

O289

Methods (reference in parentheses) CID

References (1) 1995KIC/ARM(b) (2) 1995KIC/ARM (3) 1986HAY/KRU

CID

1986HAY/KRU

Kinetics

2003SCH/HAL

(1) IR radiation

(1) 1998ROD/JOC

(2) HP MS

(2) 1990BLA/JAY(b)

(3) Extrapolate

(3) This volume

Ni–C bonds NiC(tmc)–CH2K4-C6H4X XZH

19G1

80G4

F

18G2

75G8

Cl

16G6

67G25

tmcZ1,4,8,11-tetramethyl1,4,8,11-tetra-azacyclotetradecane

Ni2C(H2O)x–H2O xZ5

(1) 24.1G1.0

100.8G4.2

6

(1) 17.6G0.8

73.6G3.3

7

(1) 17.1G0.7

71.5G2.9

(2) 15G3

62.8G12.6

8 9

(2) 15G3 (2) 15G3

62.8G12.6 62.8G12.6

10

(2) 14G3

58.6G12.6

11

(2) 14G3

58.6G12.6

12

(2) 14G3

58.6G12.6

N

(3) w10.5

w44

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

931

20.1.3 NiK–X bonds Table 20.1.3 BDEs of NiL–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

NiK–Ni

(1) 43.3G0.7 (2) 42.7G0.3

181.2G2.9 178.5G1.4

(1) PES (2) Derived

(1) 1993HO/POL (2) 1995PIN/LAN

NiK–Cu

(1) 40.1G0.5 (2) 39.9G2.4

167.7G1.9 167G10

(1) Derived (2) Derived from EA in ref.

(1) 1996WAR/GUN (2) 1996NIST

NiK–H

44.7G2

187G8

Derived

1991ARM/SUN

(CO)5NiK–Cl –Br –I

79.2 70.9 55.0

331.4 296.6 230.1

Kinetics

1989JON/MCD

(O)NiK–O

129.0

539.5

Derived from DfH0 in ref.

1996NIST

(1) (2) (1) (2) (1) (2)

88G63 136G24 213G63 182G24 96G38 161G10

(1) Laser PES (2) CID

(1) 1982STE/FEI (2) 1992SUN/SQU

NiK(CO)x–CO xZ0 1 2

21G15 32.4G5.8 51G15 43.4G5.8 23G9 38.5G2.3

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

References

932

Comprehensive Handbook of Chemical Bond Energies

20.2 Pd–, PdC–, and PdK–X bonds 20.2.1 Pd–X bonds Table 20.2.1 BDEs of Pd–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Pd–Pd

(1) (2) (3) (4) (5)

Pd(100, surf)–Pd

26G5 25.8 24.6G3.6 O32.5 18.4

kJ/mol

Methods (reference in parentheses) MS Review MS Spectroscopy Review

References

109G21 108 102.9G15 O136 77.0

(1) (2) (3) (4) (5)

12–14 (phys)

50–59

LEED

1993EVA/SAN

Pd(100, surf)–Pd

89

372

Review

1995SEE/ALL

Pd(111, surf)–Pd

17.5G1.8 (phys)

73.3G7.7

PACT

1990HUN/HAA

Pd–Ni

33.7

140.9

Spectroscopy

1990TAY/SPA(b)

Pd–Pt

45.7

191.0

Spectroscopy

1990TAY/SPA(b)

Pd(111, surf.)–K

3.0 (phys)

12.6

PEEM

1993OND/STE

Pd(111, surf.)–K

29

121

Review

1995SEE/ALL

Pd(111, surf.)–Ca

83–86

347–360

LEED

2004JER/PRI

Pd–Ba

53.0G1.2

221.8G5.0

MS

1978GIN/CHO

Pd–Y

57.6G3.6

241G15

MS

1989CHA/GIN

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

(1) (2) (3) (4) (5)

1969LIN/KAN(b) 1979MIE/GIN 1984SHI/GIN 1990TAY/SPA 1996SMI/YAT

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

933

Pd–Ce

76.2G5

319G21

MS

1989CHA/GIN

Pd(100, surf)–Ag

8.5G0.7 (phys)

35.7G2.9

HAS

1996FEL/VAN

Pd–Au

34.1G5

142.7G21

Review

1986MOR

Pd–Al

60.8G2.9

254.4G12.1

MS

1976COC/GIN

Pd(100, 2x2, surf.)–Al

9.5G0.5 (phys)

39.6G1.9

LEIS

2004GLA/SAM

Pd(110, surf.)–He

0.15

0.6

HAS

1983RIE/STO

Pd(100, surf.)–Kr

4.5

18.8

LEED

1984MOO/WEB

Pd(100, surf.)–Xe

(1) 7.6 (2) 9.4 (3) 6.2

31.8 39.3 26.1

LEED

(1) 1971PAL (2) 1984WAN/HUL (3) 1984MOO/WEB

Pd(110, surf.)–Xe

10.2

42.7

LEED/UPS

1984WAN/HUL

Pd(111, surf.)–Xe

(1) 8.3 (2) 7.4G0.2

34.7 30.9G1.0

(1) LEED/UPS (2) LEED/TPD

(1) 1984WAN/HUL (2) 2003ZHU/ELL

Pd–H

56G6

234G25

Ion reactions

1986TOL/BEA

Pd(polycs. surf.)–H

13–14 (a-state) 22 (b1-state) 23 (b2-state) 35 (b3-state)

54–59 92 96 146

TDS

1971ALD/SCH

Pd(100, surf.)–D

12.0 (phys)

50.2

TDS

1988BES/STE

(continued)

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

934

Comprehensive Handbook of Chemical Bond Energies

Table 20.2.1 (continued) BDEs of Pd–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pd(100, surf.)–H

63.6

266

Review

1998CHR

Pd(110, surf.)–H

64

267

Review

1974CON/ERT

Pd(111, surf.)–H

62

259

Review

1974CON/ERT

Pd(110, surf.)–Cl

65

272

TDS

1982ERL

Pd(111, surf.)–Cl

60.5

253

TDS

1980ERL

Pd–O

(1) 91 (2) 56.9G3

381 238.1G12.6

(1) Review (2) MS

(1) 1990SIM/BEA (2) 2000HIL/LAU

Pd(surf.)–O

86

360

TPD

1994MAD/ROB

Pd(100, surf.)–O

12.5G1

52.3G4.2

LEED

1987CHA/THI

Pd(110, surf.)–O

(1) (2) (3) (1) (2) (1) (2)

335 351–416 393.7 351 382.8 364 364.8

(1) LEED/MS (2) Review (3) Review

(1) 1969ERT/RAU (2) 1991BEN (3) 2003ZEI

414 385

Review

1982BAR/AGR

Pd(100, surf.)–O Pd(111, surf.)–O

Pd(100, surf.)–S Pd(111, surf.)–S

99 92

80 83.9–99.4 94.1 84.0 91.5 87 87.2

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

935

Pd(100, surf.)–N Pd(110, surf.)–N Pd(111, surf.)–N

136.5 140.4 130.0

571.1 587.4 543.9

Review

2003ZEI

Pd–B

(1) 78.6G5 (2) 84G4

329.0G21 351.5G16.7

(1) MS (2) Review

(1) 1970MAH/PEE (2) 1974GUR/KAR

Pd–C

104.2G4.8

436G20

Review

1990SIM/BEA

Pd(111, surf.)–C

25.6 (phys.)

107

TPD

2006GAB/HAY

Pd–Si

62.4G2.9

261G12

MS

1987SHI/KIN

Pd–Ge

(1) 61.3G2.9 (2) 62.9G2.4 (3) 60.9G2.5

256.6G12 263G10 254.7G10.5

(1) MS (2) Review (3) MS

(1) 1971PEE/MAH (2) 1985GIN/SHI (3) 1986SHI/KIN

Pd(polycr. surf.)–H2

(1) 28.7–29.9 (2) 17.9–22.7

120–125 75–95

Calorimetry

(1) 1978COU/JOH (2) 1987WED

Pd(100, surf.)–H2

24.5

102.5

LEED

1980BEH/CHR

Pd(110, surf.)–H2

5.4 (phys)

22.6

Kinetics

1986PED/KAY

Pd(110, surf.)–H2

24.4

102.1

TDS

1974CON/ERT

Pd(111, surf.)–H2

(1) 20.8 (2) 20.0

87.0 83.7

TDS

(1) 1974CON/ERT (2) 1982KIS/BLI

Pd(100, surf.,-S)–H2

20.3

85

TPD

1990BUR/MAD

Pd(110, surf.)–D2

22.8

95.4

TDS

1974CON/ERT

(continued)

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

936

Comprehensive Handbook of Chemical Bond Energies

Table 20.2.1 (continued) BDEs of Pd–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pd(111, surf.)–Cl2

45.4

190

TDS

1980ERL

Pd–O2

19–37

80–155

Kinetics

2003CAM/PLA

Pd(polyc. surf.)–O2

(1) w67 (2) 68 (3) 40.6

w280 285 170

(1) Calorimetry (2) Calorimetry (3) Review

(1) 1960BRE/HAY (2) 1965BRE/HAY (3) 1982RAO/KAM

Pd(111, surf.)–O2

(1) 12.3 (phys. a1-state) (1) 9.1 (a2-state) (1) 7.6 (a3-state) (2) 7.3

51.5

(1) TPD

(1) 1989GUO/HOF

38.1 31.8 30.9

(2) EELS

(2) 1998NOL/LUT

Pd(111, surf.)–O2

(1) w55 (2) 53

w230 222

TPD

(1) 1977CON/ERT (2) 1989GUO/HOF

Pd(surf.)–OH

(1) 60G3 (2) 51 (3) 48

251G13 213 201

(1) Adsorption (2) Adsorption (3) Desorption

(1) 1983FUJ/SEL (2) 1984STU/JOR (3) 1992AND/MOO

Pd(polyc. surf.)–N2

6–10

25–42

TD

1968KIN

Pd(100, surf.)–NO

(1) 37.0 (2) 26.3

155 110

(1) Calorimetry (2) Calorimetry, updated

(1) 1997YEO/VAT (2) 1998BRO/KOS

Pd(110, surf.)–NO

29.6

124

TPD

1993RAV/HAR

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

937

Pd(111, surf.)–NO

(1) 31 (2) 38

130 159

(1) Review (2) TPD

(1) 1979ERT (2) 1991WIC/BAN

Pd(polyc. surf.)–CO

(1) 48 (2) R38 (3) 41.1

201 R159 172

(1) Calorimetry (2) IR (3) Review

(1) 1965BRE/HAY (2) 1967KAV/SOK (3) 1996CER

Pd(100, surf.)–CO

(1) (2) (3) (4) (5)

36.5 38.5 38 39.4 39.0

153 161 159 165 163

(1) FDMS (2) TDS (3) IRAS (4) Calorimetry (5) Calorimetry, updated

(1) (2) (3) (4) (5)

Pd(110, surf.)–CO

4.8 (phys) 9.0

20 38

TD

1967DEG(c)

Pd(110, surf.)–CO

(1) 45.2 (2) 41 (3) 40

189 172 167

(1) TD (2) FDMS (3) FDMS

(1) 1967DEG(c) (2) 1969ERT/RAU (2) 1974CON/ERT(b)

Pd(111, surf.)–CO

(1) 12.0G0.7 (phys) (2) 4.0G0.3 (3) 2.7G0.1

50G2.9

(1) PEEM

(1) 1992OER/ROT

16.7G1.2 11.4G0.5

(2) PEEM (3) STM

(2) 1997SNA/BOR (3) 2005MIT/ROS

Pd(111, surf.)–CO

(1) (2) (3) (4) (5)

142 132 140 148.5 125.5

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Pd(210, surf.)–CO Pd(311, surf.)–CO

35 35.5

146 149

FDMS

1974CON/ERT(b)

Pd(100, surf.)S–CO

9

38

TDS

1988YAM/RUN

34 31.5 33.4 35.5 30

FDMS TDS TPD TPD IRAS

1974CON/ERT(b) 1980BEH/CHR(b) 1993SZA/KUH 1997YEO/VAT 1998BRO/KOS

1974CON/ERT(b) 1982KIS/BLI 1986NOO/KOK 1989GUO/YAT 1993SZA/KUH

(continued)

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

938

Comprehensive Handbook of Chemical Bond Energies

Table 20.2.1 (continued) BDEs of Pd–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Au(111, surf.)/Pd–CO

32

133.9

TPD

1994SEL/KOE

MgO(100, surf.)/ Pd–CO

16.1G2.3

67.5G9.6

TDS

2001ABB/RIE

Pd(100, surf.)–PbO

131.4

550

UPS

1982BAD/RIC

Pd(111, surf.)–NO2

14–16

59–67

TPD

1991WIC/BAN

Pd(100, surf.)–CH3Cl

46.9

196

TPD

1990SOL/BER

Pd(100, surf.)–CH3OH

9.0

37.7

EELS

1982CHR/DEM

Pd(100, surf.)–C2H2 –C2H4

26.8 17.4

112 73

Calorimetry

2000VAT/YEO

Pd(111, surf.)–C2H2

4.2

17.4

STM

1998DUN/ROS

Pd(110, surf.)–C2H4

12.9–13.4

54–56

STM

1998ICH/YOS

Pd(111, surf.)–C2H4

w12.9

w54

Mol. beam

1984TYS/NYB

Pd(111, surf.)–C3H6

18.9G0.2

79.2G0.9

TPD

1999THO/ABD

Pd(110, surf.)–C6H6

w13.1 (phys)

w55

STM

1996YOS/TAN

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

939

Pd(110, surf.)–C6H6

25.4

106.1

STM

1991FUJ/SEK

Pd(111, surf.)–RCl RZCH3(CH2)n, nZ0–5

14.3–15.3

60–64

Desorption

2000ZHO/GEL

Pd(111, surf.)–C6H6

40.6G1.7

170G7

Desorption

2004ROC/ARN

Pd–(h3C3H5Ch3C5H5)

53.0

221.9

EID

1994SAU/ERM

Pd(110, surf.)–PVBA PVBAZ4-trans-2(pyrid-4-yl-vinyl) benzoic acid

19.1G0.7

80.1G2.9

STM

1999WEC/BAR

Pd(110, surf.)–C60

32.3G0.5

135.1G1.9

Review

2003ROS/SCH

20.2.2 PdC–X bonds Table 20.2.2 BDEs of PdD–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

Methods (reference in parentheses)

kcal/mol

kJ/mol

PdC–Pd

(1) 39G12 (2) 47.2G6.9

163G50 197G29

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

PdC–H

(1) (2) (3) (4) (4)

188G13 203.3G3.8 208.4G8.7 275G5 146.7G11.6

Ion reactions

(1) (2) (3) (4)

528G5 536G10 463G3

Ion reactions

(1) 2001ZHA/LIY

–H2

PdC–C –CH –CH2

45G3 48.6G0.9 49.8G2.1 65.7G1.2 35.1G2.8

(1) 126.2G1.2 (1) 128.2G2.3 (1) 110.7G0.7

References

1984MAN/HAL 1995CHE/ELK 1997CHE/SIE 2001ZHA/LIY

(continued)

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

940

Comprehensive Handbook of Chemical Bond Energies

Table 20.2.2 (continued) BDEs of PdC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

PdC(CH3)x–CH3 xZ0

1

Methods (reference in parentheses)

kcal/mol

kJ/mol

(2) 115G4 (3) 68.1G1.2

481G17 285G5

(1) (2) (3) (4)

247G21 181.4G9.6 258G8 O155

Ion reactions

(1) 1984MAN/HAL (2) 1997CHE/SIE (3) 2001ZHA/LIY (4) 1990SIM/BEA

59G5 43.4G2.3 61.6G1.8 O37

References (2) 1994WES/SCH (3) 1999ARM(c)

PdC–CH4

40.8G1.8

170.8G7.7

Ion reactions

2001ZHA/LIY

PdC–C2H2 –C2H3 –C2H4

(1) (1) (1) (2) (1)

O28.9G4.8 247.0G8.7 O67.5 117.2 233.5G4.8

(1) Ion reactions

(1) 1997CHE/SIE

(2) Review

(2) 1998SCH/SCH

–C2H5

O6.9G1.2 59.0G2.1 O16.1 28 55.8G2.1

PdC–C3H3 –C3H5 –C3H6

55–78 O78 O26

230–326 O328 O108

Ion reactions

1997CHE/SIE

PdC–O

34.7G2.5

145G11

CID

1995CHE/ARM(c)

PdC–S

47.1G1.4

197G6

Ion reactions

2003ARM

PdC–Si

69G12

289G50

Derived

1974GUR/KAR

PdC–CS

47.8G3.3

200G14

CID

2000ROD/ARM(b)

7366—CHAPTER 20—3/2/2007—11:34—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

941

20.2.3 PdK–X bonds Table 20.2.3 BDEs of PdL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

PdK(Pd)x–Pd xZ0 1 2

(1) 50.5G3.9 (2) 52.6G9.6 (2) R57.4G9.6

211.2G16 220G40 R240G40

(1) PES (2) CID

(1) 1991HO/ERV (2) 1998SPA/ERV

PdK(Pd)2(CO)x–CO xZ0 1 2 3 4 5

40.6G7.2 40.4G5 33.9G5 26.1G3.3 25.6G3.3 26.3G3.8

170G30 169G21 142G21 109G14 107G14 110G16

CID

1998SPA/ERV

20.3 Pt–, PtC–, and PtK–X bonds 20.3.1 Pt–X bonds Table 20.3.1 BDEs of Pt–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pt–Pt

(1) 86.3G3.6 (2) 73.3G0.5

361G15 306.7G1.9

(1) MS (2) Spectrometry

(1) 1981GUP/NAP (2) 1988TAY/LEM

Pt–Pt(N2)

w9.2

w38.6

PEDt

2005NEE/STA

Pt(100, surf.)–Pt

10.8G0.2

45.3G1.0

FIM

1990KEL/FEI

Pt(100, surf.)–Pt2

9.5

39.6

FIM

1991KEL/VOT

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

942

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pt(100, surf.)–Pt3

13.1

55.0

FIM

1994KEL(b)

Pt(110, surf.)–Pt

19.4G2.3

81.0G9.6

FIM

1978BAS/WEB

Pt(111, surf.)–Pt

(1) 5.8G0.5 (phys) (2) 6.0 (3) 6.0G0.1

24.1G1.9

(1) FIM

(1) 1994FEI/NEL

25.1 25.1G0.3

(2) STM (3) STM

(2) 1996BOT/HOH (3) 1998KYU/GOL

Pt(111, surf.)–Pt2

8.5G0.5

35.7G1.9

STM

1998KYU/GOL

Pt(311, surf.)–Pt

(1) 15.9G4.6 (2) 13.8G0.7

66.6G19.3 57.9G2.9

FIM

(1) 1978BAS/WEB (2) 1986KEL

Pt(331, surf.)–Pt

19.4G2.3

81.0G9.6

FIM

1978BAS/WEB

Pt–Ni

65.4G0.1

273.7G0.3

Spectrometry

1990TAY/SPA(b)

Pt(100, surf.)–Ni

w10.4 (phys)

w43.4

FIM

1991KEL/WRI

Pt–Pd

45.7

191.0

Spectrometry

1990TAY/SPA(b)

Pt(100, surf.)–Pd

16.1 (phys)

67.5

FIM

1991KEL/WRI

Pt(100, surf.)–Pd

100

418

Review

1995SEE/ALL

Pt(111, surf.)–Na

!1.2 (phys)

!4.8

Scattering

2001GRA/TOE

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

Pt(111, surf.)–K

(1) 65 (2) 63.7

Pt(polycr. surf.)–Ba

272 266.5

943

TDS

(1) 1982GAR/SOM (2) 1986ALB

31.1G23.1 (phys) 130.3G9.6

FEM

1976KUL

Pt(polycr. surf.)–Ba

(1) 126.7 (2) 115

530 481

(1) FEM (2) Review

(1) 1976KUL (2) 1995SEE/ALL

Pt–Ti

95.0G2.5

397.5G10.6

Review

1986MOR

Pt–Y –La –Ce –Lu

113.3G2.9 120.7G2.9 131.5G1.2 96.1G8

474G12 505G12 550G5 402G34

MS

1989CHA/GIN

Pt–Th

131.6G10

551G42

MS

1973GIN

Pt(111, surf.)–W

7 (phys)

29

FIM

1978BAS/WEB

Pt(111, surf.)–W

150

628

Review

1995SEE/ALL

Pt(311, surf.)–Ir Pt(110, surf.)–Ir

17.1G3.5 18.4G3.5

71.4G14.5 77.2G14.5

FIM

1978BAS/WEB

Pt(111, surf.)–Ag

3.6 (phys)

15.1

TSM

1994BRU/ROD

Pt(111, surf.)Ag–Ag

1.4G0.2 (phys)

5.8G1.0

STM

1995BRU/BRO

Pt(311, surf.)–Au Pt(110, surf.)–Au

12.9G2.3 14.5G3.5

54.0G9.6 60.8G14.5

FIM

1978BAS/WEB

Pt(110, surf.)–He

0.20

0.84

HAS

1990KIR/PAR

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

944

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pt(111, surf.)–He

(1) 0.2 (2) 0.1

0.8 0.4

HAS

(1) 1972WEI (2) 1989BOR/CEL

Pt(111, surf.)–Ne

0.3

1.4

Calorimetry

1962CHO/FIS

Pt(111, surf.)–Ar

1.3

5.5

Calorimetry

1962CHO/FIS

Pt(111, surf.)–Kr

1.1

4.6

TITD

1993MEI/GEO(b)

Pt(111, surf.)–Kr

(1) 3.7G0.1 (2) 3.1

15.5G0.4 12.9

(1) LITD (2) Mol. beam

(1) 1993MEI/GEO(b) (2) 2001CAR/MAD

Pt(111, surf.)–Xe

1.2

5.0

LITD

1993MEI/GEO

Pt(111, surf.)–Xe

(1) (2) (3) (4) (5)

26.4 26.0 39.5G3.9 27.6G0.8 28.1

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Pt(997, surf.)–Xe

7.0

29.2

TDS

1998WID/TRI

Pt–H

(1) 80.1 (2) 84.1G9 (3) 79.0

%335 352G38 330

(1) Spectroscopy (2) Review (3) FT–ICR

(1) 1979HUB/HER (2) 1990SIM/BEA (3) 1999DIE/BRO

Pt–D

%83.7

%350.2

Spectroscopy

1979HUB/HER

6.3 6.2 9.5G0.9 6.6G0.2 6.7

HAS Scattering Scattering LITD TDS

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

1986KER/DAV 1990ARU/MAD 1990RET/BET 1993MEI/GEO 1998WID/TRI

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

945

Pt2(H)x–H xZ0 1

w47G3.8 R47

w197G15.9 R197

Est. by exp.

1991HER/GOO

Pt2 ðP2 O5 H2 Þ44KKH

103

431

PAC

1991HER/GOO

trans-Pt(PPh3)2(Cl)–H

73.4G8.8

307G37

Calorimetry

1994NOL

[Ph2PCH2]2MePt–H

25.0

104.6

Review

1992DRA/WON

Pt(polycs. surf.)–H

w4.5 (phys)

w19

FEM

1969LEW/GOM

Pt(polycs.surf.)–H

(1) 60.9 (2) 61.7

255 258

Pt(100, surf.)–H

59

247

Review

1991BEN

Pt(110, surf.)–H

(1) 58 (2) 63.0

243 263.5

(1) Review (2) Adsorption

(1) 1991BEN (2) 1995PAS/WAR

Pt(111, surf.)–H

6.9 (phys)

28.9

LERS

1997UME/ITO

Pt(111, surf.)–H

(1) 56.7 (2) 61.9

237.5 259

Adsorption

(1) 1976CHR/ERT (2) 1977MCC/SCH

(1) 55–62 Pt(surf.)–Hupd (under potentially deposited (2) 58.6–63.3 hydrogen)

230–260 245–265

Electrochemical

(1) 1997ZOL/BLA (2) 1997ZOL/CHA

Pt(111, surf.)–Hupd (underpotentially deposited hydrogen)

250–262 240

(1) 60–63 (2) 57.5

(1) Review (2) Electrochemical

Electrochemical

(1) 1988CHR (2) 2004GOM/ORT

(1) 1997ZOL/JER (2) 1999MAR/SCH

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

946

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pt(111, surf.)–Hupd (in aqu. H2SO4), (underpotentially deposited hydrogen)

45.7–52.1

191–218

Electrochemical

2005JER/DEB

Pt(111, surf.)–Hchem (chemisorbed hydrogen)

60.9

255

Electrochemical

1999ZOL/JER

MoPt3 –Hupd (underpotentially deposited hydrogen)

66.7

279

Electrochemical

2004JAK/KRA

MoPt4–Hupd (underpotentially deposited hydrogen)

50.9

213

Electrochemical

2004VRA/KRS

Pt2–Cl

49.9G2.4

208.8G10

PAC

1991HER/GOO

Pt2 ðP2 O5 H2 Þ44K– Cl

106

443.5

PAC

1991HER/GOO

Pt(110, surf.)–Cl

59.5

249

TDS

1982ERL

Pt(111, surf.)–Cl

47.5

199

TDS

1980ERL

Pt2–Br

32G3.1

133.9G13

PAC

1991HER/GOO

Pt2 ðP2 O5 H2 Þ44K– Br

88.5

370.3

PAC

1991HER/GOO

Pt(111, surf.)–Br

25.4

106.1

TPD

1998XU/YUR

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

947

Pt2–I

34G4.0

142.3G16.7

PAC

1991HER/GOO

Pt2 ðP2 O5 H2 Þ44K– I

90.5

378.7

PAC

1991HER/GOO

Pt–O

93.5G10

391G42

Review

1990SIM/BEA

Pt(surf.)–O

83

347

TPD

1994MAD/ROB

Pt(polycs. surf.)–O

39 (phys)

163

TDS

1974PEN/DAW

Pt(polycs. surf.)–O

54

226

TDS

1974PEN/DAW

Pt(100, surf.)–O

34 (phys)

142

FEM

1968LEW/GOM

Pt(100, surf.)–O

(1) 82 (2) 70 (3) 89.3

343 293 373.6

Review

(1) 1991BEN (2) 1995SEE/ALL (3) 2003ZEI

Pt(110, surf.)–O

(1) 27 (phys) (2) 30

113 126

(1) FEM (2) PEEM

(1) 1968LEW/GOM (2) 1994OER/ROT

Pt(110, surf.)–O

(1) (2) (3) (4)

58 69.3 102.1 91.8

243 290 427 384

(1) (2) (3) (4)

(1) (2) (3) (4)

Pt(111, surf.)–O

(1) 27 (phys) (2) 25.4

113 106

(1) FEM (2) TPD

(1) 1968LEW/GOM (2) 1989BAR/KOE

Pt(111, surf.)–O

(1) (2) (3) (4)

356 243 405 213

(1) (2) (3) (4)

(1) (2) (3) (4)

85 58 96.8 50.9

FEM FDMS Calorimetry Review

TPD Review Calorimetry TPD

1970FUS/EHR 1975KNE/NET 1998BRO/KOS 2003ZEI

1989PAR/BAR 1995SEE/ALL 1998BRO/KOS 2005WEA/CHE

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

948

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pt(111, surf.)–Oad (adsorpted)

w83.7

w350

Electrochemical

1999MAR/SCH

Pt(111/0001, surf.)–O

85.0

355.6

Review

2003ZEI

Pt(112, surf.)–O

84.3

353

Review

1991BEN

Pt(111, surf.)–S

13.1G1.2 (phys)

55.0G4.8

STM

2000BAR

Pt–N

89.4G2.3

374.2G9.6

GIB MS

2004ZHA/ARM

Pt(foil)–N

121

506

Review

1991BEN

Pt(100, surf.)–N Pt(110, surf.)–N Pt(111/0001, surf.)–N

121.8 125.3 116.0

509.6 524.3 485.3

Review

2003ZEI

Pt–P

%99.6G4

%416.7G16.7

MS

1971SMO/HUG

Pt(111, surf.)–Bi

81

339

TDMS

1986PAF/CAM

Pt–C –C2

145.8G1.2 133

610G5 557

Review

1990SIM/BEA

Pt(111, surf.)–C

w31G4 (phys)

w130G17

AES

1978MAR/HUD

Pt(111, surf.)–C

146

611

Review

1955SEE/ALL

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

949

Pt–Si

119.8G4.3

501G18

MS

1970MAN/PEE

Pt–B

114.2G4.0

478G16.7

MS

1968MCL/MAH

Pt(polycr. surf.)–H2

(1) (2) (3) (4) (5)

109 67 68 103 81–90

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Pt(100, surf.)–H2

15–16

63–67

FDMS

1975NET/KNE

Pt(100, 1!1, surf.)–H2

22.6

94.6

TPD

1998LEE/FOR

Pt(Hex-100, surf.)–H2

23.7

99.1

Pt(110, surf.)–H2

(1) 24.4

102.1

(1) TDS

(1) 1974CON/ERT

(2) 17

71

(2) Review

(2) 1978MAD/BEN

Pt(110, 1!1, surf.)–H2

28.1

117.5

TPD

1998LEE/FOR

Pt(110, 2!1, surf.)–H2

(1) 18

75.3

TPD

(1) 1987ENG/TSA

(2) 17.7

74.0

(1) 9.5 (phys)

39.7

(1) TDS

(1) 1976CHR/ERT

(2) 1.7 (3) 7G1 (4) 1.57G0.16

6.9 29G4 6.56G0.48

(2) Scattering (3) LITD (4) Scattering

(2) 1983COW/YU (3) 1986SEE/SCH (4) 1999GRA/MEN

(1) 20.8 (2) 17.5 (3) 22.9

87.0 73.2 95.8

(1) TDS (2) TDS (3) TPD

(1) 1974CON/ERT (2) 1977MCC/SCH (3) 1998LEE/FOR

Pt(111, surf.)–H2

Pt(111, surf.)–H2

26 16 16.3 24.6 19.4–21.5

TD TD TD Calorimetry Calorimetry

1963WIE 1969LEW/GOM 1972PRO/VOE 1974NOR/RIC 1975CER/SMU

(2) 1998LEE/FOR

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

950

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pt(111, surf.)–D2

(1) 7G1 (phys) (2) 1.75G0.16

29G4 7.33G0.67

(1) LITD (2) Scattering

(1) 1986SEE/SCH (2) 1999GRA/MEN

Pt(111, surf.)–D2

16.0G1.7

67G7

Nuclear anal.

1982NOR/DAV

Pt(331, surf.)–H2

18.6

77.8

TPD

1998LEE/FOR

Pt(410, surf.)–H2

18.7

78.2

Pt(111, surf.)–HD

(1) 1.3G0.2 (phys)

5.3G1.0

Scattering

(1) 1983COW/YU

(2) 1.27

5.31

Pt(111, surf.)–Cl2

35.5

149

TDS

1980ERL

Pt(111, surf.)–HCl

4.5 (phys)

18.7

TPD

2005DAS/KIM

Pt(111, surf.)–HCl

21.5

90

TPD

2005DAS/KIM

Pt(polycr. surf.)–O2

(2) 1984WHA/LIG

(1) 68.8–72

288–301

(1) Calorimetry

(1) 1960BRE/HAY

(2) 70 (3) 58 (4) 31.8

293 243 133

(2) Calorimetry (3) TD (4) Review

(2) 1965BRE/HAY (3) 1969WEB/FUS (4) 1982RAO/KAM

Pt(100, surf.)–O2

44.7–69.3

187–290

Review

1979TOY/SOM

Pt(110, surf.)–O2

(1) 80.1 (2) 86.0

335 360

(1) Calorimetry (2) Updated

(1) 1996WAR/STU (2) 1998BRO/KOS

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

951

Pt(110, 2!1, surf.)–O2

52.0

217.6

TPD

1998LEE/FOR

Pt(111, surf.)–O2

9.9 (phys)

41.5

STM

1996WIN/SCH

Pt(111, surf.)–O2

(1) 6.7 (peroxo-) (2) 3.0 (superoxo-)

28.0 12.5

Mol. beam

1999NOL/LUT

Pt(111, surf.)–O2

45.5 (b1 state) 49.6 (b2 state)

190 208

TPD

1988WIN/GUO

Pt(111, surf.)–O2

(1) (2) (3) (4)

213 213 339G32 316

(1) (2) (3) (4)

(1) (2) (3) (4)

(5) 48.0

201

Mol. beam TPD Calorimetry Calorimetry, updated (5) TPD

7.7 (phys. a1 state) 9.8 (a2 state) 13.1 (a3 state)

32.2

TDS

1988SID/WIN

Pt(331, surf.)–O2

45.4–49.8

190–208

TPD

1998LEE/FOR

Pt(511, 1!1, surf.)–O2

49.2

206

TPD

1998LEE/FOR

Pt–CO

76.5G12

320G50

CID

1997GRU/ERV

Pt(nanoparticles)–CO

6.0G0.4 (phys)

25.1G1.7

NMR

2005KOB/BAB

Pt(foil, surf.)–CO

43.7–52.6

183–220

TDS

2000OST/BEH

Pt(polycs. surf.)–CO

14–15 (phys)

59–63

FEM

1967LEW/GOM

Pt(211, surf.)–O2

50.9 51 81.0G7.6 75.5

1981CAM/ERT 1989PAR/BAR 1996WAR/STU 1998BRO/KOS

(5) 1998LEE/FOR

41.0 54.8

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

952

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Pt(polycs. surf.)–CO

(1) (2) (3) (4)

Pt(100, hex, surf.)–CO

43 32 R44 48.0

kJ/mol

Methods (reference in parentheses)

180 134 R184 201

(1) (2) (3) (4)

25.1

105

Mol. beam

1993HOP/GUO

Pt(100, 1!1, surf.)–CO

(1) (2) (3) (4) (5)

156.9 156.9 154 215 220

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Pt(100, hex, surf.)–CO

(1) 42.8G0.7 (2) 46.1

179G3 193

(1) Calorimetry (2) Calorimetry, updated

(1) 1996YEO/VAT (2) 1998BRO/KOS

Pt(110, surf.)–CO

(1) 2.5 (phys) (2) 9

10.5 38

(1) LEED (2) PEEM

(1) 1982UNE/JAC (2) 1994OER/ROT

Pt(110, surf.)–CO

(1) (2) (3) (4) (5)

142 148 160G15 183 193

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Pt(110, 1!1, surf.)–CO

8.9–10.0 (phys)

37–42

PEEM

1994OER/ROT

Pt(110, 1!1, surf.)–CO

29.3

123

TPD

1998LEE/FOR

37.5 37.5 36.8 51.4 52.6

34 35.3 38.2G3.6 43.7 46.1

Calorimetry FEM IR Calorimetry

References

TPD Kinetics TDS Calorimetry Calorimetry, updated

FDMS MBRS LITD Calorimetry Calorimetry, updated

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

(1) (2) (3) (4)

1965BRE/HAY 1967LEW/GOM 1967KAV/SOK 1996CER

1983THI/BEH 1991FIN/DAT(b) 1993HOP/KIN 1996YEO/YAT 1998BRO/KOS

1974CON/ERT(b) 1980FAI/MAD 1982UNE/JAC 1997YEO/VAT(b) 1998BRO/KOS

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

953

Pt(110, 2!1, surf.)–CO

11.1–13.1 (phys)

46–55

PEEM

1994OER/ROT

Pt(110, 2!1, surf.)–CO

28.7

120

TPD

1998LEE/FOR

Pt(111, surf.)–CO

(1) 4.0G0.7 (phys) (2) 6.0G0.3 (3) 3.6G0.7 (4) 3.0 (5) 3.0–4.7 (flat) (5) 7.3–7.9 (step)

16.7G2.9

(1) IRAS

(1) 1990ROB/DOR

25.1G1.3 15.1G2.9 12.5 13–20 31–33

(2) (3) (4) (5)

Scattering IRAS HAS LOD

(2) (3) (4) (5)

1993CRO/FEL 1994NEK/HAR 1998GRA/TOE 1998MA/XIA

Pt(111, surf.)–CO

(1) (2) (3) (4) (5)

133 133.9G8.4 133.9G8.4 144.7 192.5G12.6

(1) (2) (3) (4) (5)

HAS LITD TPD HAS TDS

(1) (2) (3) (4) (5)

1984POE/PAL 1987SEE/KON 1990KIS/SZA 1998GRA/TOE 2002HAN/LEE

Pt(111, surf.)S–CO

22G2

92.0G8.4

TPD

1990KIS/SZA

Pt(111, surf.)Se–CO

23G2

96.2G8.4

TPD

1990KIS/SZA

Pt(211, surf.)–CO

(1) 34.1 (2) 40.6

142.7 170

(1) TPD (2) Calorimetry

(1) 1998LEE/FOR (2) 2003KAR/FIO(b)

Pt(331, surf.)–CO

31.1

130.0

TPD

1998LEE/FOR

Pt(410, surf.)–CO

32

134

TPD

1985PAR/BAN

Pt(511, 1!1, surf.)–CO

32.4

135.6

TPD

1998LEE/FOR

Pt(111, surf.)/La–CO

20.8G2.3

86.8G9.6

TPD

1999RAM/RAA

Pt(100, surf.)NO–CO

12

50

TDS

1991FIN/DAT

31.8 32G2 32G2 34.6 46G3

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

954

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pt(111, surf.)Cu–CO

15.8–17.0

66–71

TDS

1983SHE/STE

Pt(331, surf.)–OH

60

251

Est. by exp.

1985STU/THI

Pt(211, surf.)–C (in C2H2)

w52.6

w220

TPD

1999KOS/BRO

Pt(111, surf.)–OHad (adsorpted)

32.5

136

Electrochemical

1999MAR/SCH

[Ph2PCH2]2MePt–OH –SH –CN

40.0 21.5 54.2

167.4 90.0 226.8

Review

1992DRA/WON

Pt(100, surf.)–N2

9 (phys)

38

Correlation

1981NIE

Pt(100, surf.)–N2

20.2

84.5

Est. by exp.

1991FIN/DAT

Pt(111, surf.)–N2

w9.6 (phys)

w40

IRAS

1977SHI/KIN

Pt(111, surf.)–N2

19 (phys)

80

TDS

1976WIL/DAW

Pt(111, surf.)–N2

62

259

TDS

1976WIL/DAW

Pt(211, surf.)–N2

9 (phys)

38

Correlation

1981NIE

Pt(filement, surf.)–N2

w22

w92

TDS

1976WIL/DAW

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BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

955

Pt(100, hex, surf.)–NO

(1) (2) (3) (4)

26.0 25.1 42.3G1.4 44.7

109 105 177G6 187

(1) (2) (3) (4)

TDS TDS Calorimetry Calorimetry, updated

(1) (2) (3) (4)

1991FIN/DAT 1993HOP/KIN 1996YEO/VAT 1998BRO/KOS

Pt(100, 1!1, surf.)–NO

(1) (2) (3) (4) (5)

36 37.0 36.8 47.8G2.4 45.7

151 155 154 200G10 191

(1) (2) (3) (4) (5)

Kinetics Kinetics TDS Calorimetry Calorimetry, updated

(1) (2) (3) (4) (5)

1981GOR/SCH 1991FIN/DAT(b) 1993HOP/KIN 1996YEO/VAT 1998BRO/KOS

Pt(110, 2!1, surf.)–NO

(1) 33.5 (2) 38.2 (3) 38.7

140 160 162

(1) Kinetics (2) Calorimetry (3) Calorimetry, updated

(1) 1981GOR/SCH (2) 1996WAR/STU (3) 1998BRO/KOS

Pt(111, surf.)–NO

(1) 5 (phys) (2) 11.8

21 49.4

(1) Mol. Beam (2) HAS

(1) 1983SER/TUL (2) 1994CRO/FEL

Pt(111, surf.)–NO

(1) (2) (3) (4) (5)

120 105 138 108.8G8.4 124.7G4.2

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Pt(210, surf.)–NO

35.0

146

TDS

1986LAN/MAS

Pt(411, surf.)–NO

28.6

120

TPD

1989GOH/MAS

Pt(557, surf.)–NO

32.3

135

TPD

1981LIN/SOM

Pt(111, surf.)–CO2

2.5

10.5

TDS

1983MAT

Pt(111, surf.)–H2O

(1) 12 (2) 10.1 (3) 9.6

50 42.3 40.2

(1) TDS (2) TPD (3) STM

(1) 1980FIS/GLA (2) 1984SEX/HUG (3) 1996MOR/MIC

28.6 25 33.0 26G2 29.8G1

TPD TPS LITD LITD HAS

1981LIN/SOM 1981GOR/SCH 1983DOY/ERT 1986SEE/KON 1994CRO/FEL

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

956

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pt(111, surf.)–HCN

30.6

128

TPD

2005HER/TRE

Pt(111, surf.)–NH3

12.0

50.2

TDS

1981GLA/KOL

Pt(111, surf.)–NH3

(1) 32.3G3.0 (2) 25.4G2.3

135.1G12.5 106.1G9.6

CID

(1) 1994SZU/LEV (2) 1995SZU

Pt(h5-C5H5)(CH3)2–CH3 39G5

163G21

Kinetics

1970EGG

cis-Pt(PEt3)2(X)–CH3 xZCl I

60G7 72G8

251G30 300G34

Kinetics

1990SIM/BEA

cis-Pt(PEt3)2(CH3)–CH3

64.3G3

269G13

Review

1994NOL

[Ph2PCH2]2MePt–CH3 [Ph2PCH2]2MePt –OCH3

26.0 24.7

108.8 103.3

Review

1992DRA/WON

Pt(polycr. surf.)–CH4

36.1

151

Calorimetry

1984PAL/LIS

Pt(111, surf.)–CH4

(1) 3.6G0.15 (phys) (2) 3.8

15.1G0.6

(1) LITD

(1) 1993MEI/GEO(b)

16.1

(2) TDS

(2) 2003WEA/CAR

Pt(111, surf.)–CH4

12.5G0.8

52.5G3.5

Mol. beam

2006DEW/VAL

Pt(111, surf.)–CH3I

11.5G0.7

48G3

TPD

1995FRE/HAR

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BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

957

(Sn)Pt(111, surf.)–CH3I

13.4

56.1

HR–EELS

2004PAN/SAM

Pt(PMe2Ph)(Cl)(Me)2 –C(O)Me

72.7G1

304G4

Review

1990SIM/BEA

Pt(111, surf.)–CH2O

11

46

Review

1988SHU

Pt(110, surf.)–CH3OH

11.4

47.5

TPD

1984SEX/HUG

Pt(110, 1!1, surf.) –CH3OH

7.4

31

TPD

1998LEE/FOR

Pt(110, 2!1, surf.) –CH3OH

12.5

52.3

TPD

1992FRA/HER

Pt(331, surf.)–CH3OH

14.0

58.5

TPD

1998LEE/FOR

Pt(511, 1!1, surf.) –CH3OH

12.5

52.3

TPD

1998LEE/FOR

Pt(111, surf.)–CCH3

55.3G4.6

231.6G19.3

TPD/SIMS

1992ZHO/LIU

Pt(polycr. surf.)–C2H2

45

188

Calorimetry

1984PAL/LIS

Pt(211, surf.)–C2H2

64.5G2.4

270G10

Calorimetry

1999KOS/BRO(b)

Pt(polycr. surf.)–C2H4

35.4

148

Calorimetry

1984PAL/LIS

Pt(100, hex, surf.) –C2H4 Pt(100, 1!1, surf.) –C2H4

19.4

81.2

TDS

1998LEE/FOR

15.8

66.1

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

958

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pt(100, hex, surf.)–C2H4 51 73 Pt(100, 1!1, surf.) –C2H4

213 305

Calorimetry

1998YEO/STU

Pt(110, surf.)–C2H4

223 235

(1) Calorimetry (2) Updated

(1) 1995STU/WAR (2) 1998BRO/KOS

Pt(110, 2x1, surf.)–C2H4 49.0

205

Calorimetry

1995STU/WAR

Pt(111, 1!1, surf.)–C2H4 11.6 Pt(111, 2!1, surf.)–C2H4 16.4

48.5 68.6

TPD

1998LEE/FOR

Pt(111, surf.)–C2H4

(1) 35.5G3.9 (2) 58.6 (3) 46.6

148.5G16.3 245 195

(1) Calorimetry (2) Calorimetry (3) Updated

(1) 1987KYS/MAS (2) 1996YEO/STU (3) 1998BRO/KOS

Pt(210, surf.)–C2H4

15.2

63.6

TPD

1998LEE/FOR

Pt(211, surf.)–C2H4 Pt(311, 1!2, surf.) –C2H4

43.0 52.6

180 220

Calorimetry

1999BRO/KOS(b)

Pt(331, surf.)–C2H4

16.4

68.6

TPD

1998LEE/FOR

Pt(511, 1!1, surf.) –C2H4

17.7

73.9

TPD

1998LEE/FOR

Pt(PPh3)2–C2H4

36.3G4.3

152G18

Review

1990SIM/BEA

(1) 53.3 (2) 56.2

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BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

959

[Ph2PCH2]2MePt –CH2CH3

21.0

87.9

Review

1992DRA/WON

trans-Pt(PEt3)2(Cl) –CH2CH3

49.2

206

Review

1990SIM/BEA

Pt(111, surf.)–CH3 –C2H5

15.4 11.5 (a-C–H) 10.5 (b-C–H) 12.9 15.0 (a-C–H) 15.0 (g-C–H)

64.4 48.1 43.9 54.0 62.8 62.8

TPD

2001ZAE

Pt(111, surf.)–CnH2nC2

w29.9

w125

Mol. beam

2000WEA/KRZ

Pt(111, surf.)–C2H6

(1) 8.8 (2) 6.3G0.7

36.8 26.5G3

(1) TDS (2) Mol. beam

(1) 2003WEA/CAR (2) 2006DEW/VAL(b)

Pt(111, surf.)/Ni–C2H6

8.7

36.6

TDS

1990ROD/GOO

Pt(polycr.)–C2H6

52.1

218

Calorimetry

1984PAL/LIS

Pt(111, surf)-cis -CHClCHC –trans -CHClCHC

w9

w38

TDS

1988GRA/PIM

w9

w38

Pt(110, surf.)–C2H5OH

12.0

50.2

TPD

1984SEX/HUG

[Ph2PCH2]2MePt –CH2C(O)CH3

20.0

83.7

Review

1992DRA/WON

Pt(polycr.)-c-C3H6

(1) w47 (2) w52

w197 w217

Calorimetry

(1) 1977CER/SMU (2) 1984PAL/LIS

–C3H7 –neo -C5H11

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

960

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pt(111, surf.)–C3H8

9.8

41.2

TDS

2003WEA/CAR

Pt(polycr.) –C3H6 –C3H8 –C(CH3)2 –HCCCH3

42.1 59.3 46.8 44.5

176 248 196 186

Calorimetry

1984PAL/LIS

Pt(110, surf.)–C3H7OH –C4H9OH

13.8 14.7

57.8 61.7

TPD

1984SEX/HUG

Pt(110, surf.) –CH3COCH3 –CH3CCN –CH3SOCH3

11.0 12.4–14.3 23.5

46.2 52–60 98.4

TPD

1984SEX/HUG

11.5

48.1

HR-EELS

1983AVE/WEI

Pt(AsMe3)2(Cl)(Me) –C2F4 –C4F6

12.4G0.2 16.5G0.5

52G1 69G2

Review

1990SIM/BEA

Pt(AsMe3)2(Br)(Me) –C2F4 –C4F6

11.5G0.2 14.6G0.5

48G1 61G2

Review

1990SIM/BEA

Pt(AsMe2Ph)2(X)(Me) –C4F6 xZCl Br

17.4G0.2 19.1G0.2

73G1 80G1

Review

1990SIM/BEA

Pt(111, surf.) –CH3COCH3

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

961

Pt(111, surf.)-n-C4H10

(1) 8.2G1.2 (2) 14.4

34.3G5.0 60.2

TDS

(1) 1981SAL/SOM (2) 2003WEA/CAR

Pt(110, surf.) –C2H5OC2H5

12.6

52.6

TPD

1984SEX/HUG

Pt(111, surf.)-n-C5H12

10.2G1

42.6G4.2

TDS

1981SAL/SOM

[Ph2PCH2]2MePt –CH2Si(Me)3

22.0

92.0

Review

1992DRA/WON

Pt(PPh3)2–C2(CN)4

(1) 54.3G8.8 (2) 66.2G8.8

227G37 277G37

Review

(1) 1990SIM/BEA (2) 1994NOL

14.8 15.9 17.2 17.7 18.5

61.9 66.4 72.0 74.2 77.2

TPD

2000BIS/GIR

(1) 28 (2) 47.1

117 197

TPD

(1) 1994XU/TSA (2) 2004IHM/AJO

[Ph2PCH2]2MePt –Ph –CCPh

31.0 54.3

129.7 227.2

Review

1992DRA/WON

Pt(PPh3)2(Cl)–C(O)Ph

O55.5

O232

Calorimetry

1990SIM/BEA

Pt(PPh3)2–CH2CHPh

40.4G8.8

169G37

Review

1990SIM/BEA

Pt(PPh3)2-cis-C2Ph2

43.2G4

181G17

Review

1990SIM/BEA

Pt(111, surf.) -n-C6H14 –n-C7H16 –n-C8H18 –n-C9H20 –n-C10H22

Pt(111, surf.)–C6H6

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

962

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.1 (continued) BDEs of Pt–X Bonds

The broken bonds (boldfaceZdissociated fragment) Pt(PPh3)2 -cis-C2H2Ph2 –trans-C2H2Ph2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

46.4G8.8 50.2G8.8

194G37 210G37

Review

1990SIM/BEA

Pt(PPh3)2-(pcbd) pcbdZplatinumbenzocyclo-pentene1,2-dione metallacycle

42.3G6.5

177G27

Review

1990SIM/BEA

Pt(Cl)2-(cod) codZ1, 5-cyclo-octadiene

95.1G5.7

398G24

Review

1990SIM/BEA

%217

Calorimetry

1980MOR/MIL

55.7 43.5 41.1

233 182 172

NMR

1997LEV/PUD

27.4G1.4 29.1G0.9 35.1G1.2

114.6G5.9 121.8G3.8 146.9G5.0

EIMS

2005HAM/GER

Pt-N bond(Cl)3Pt%51.9 (9-methyladeninium)

(XMe2)(bpy-tbu2) Pt-MMe3 xZCl, Br, I bpy-tbu2Z4, 4 0 -di-tert-butyl-2, 2 0 -bipyridyl MZSi Ge Sn

Pt-L bonds CH3Cl

Cl L

Cl

N

Pt

CH3

N

Cl CH3

LZtrifluoroethanol H2O CH3CN

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds

963

20.3.2 PtC–X bonds Table 20.3.2 BDEs of PtD–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

PtC–Pt

76.1G5.5

318G23

Spectrometry

1988TAY/LEM

PtC–Ar

8.7G2.1

36.4G8.7

Ion reactions

2003ZHA/ARM

PtC–Xe

20.7G6.9

86.6G28.9

Ion reactions

2003ZHA/ARM

PtC–H

65.7G1.2

275G5

Ion reactions

2002ZHA/ARM

PtC(Cl)x–Cl xZ0 1

59.7G3.5 61.6G4.4

249.8G14.5 257.6G18.3

CID

2003LIY/STY(b)

PtC–H2 PtC(CH2)–H2

35.1G2.8 38.7G2.1

146.7G11.6 162.1G8.7

Ion reactions

2001ZHA/LIY

PtC–C

(1) 126.1G1.2 527.6G4.8 (2) 126.8G1.2 530.5G4.8

Ion reactions

(1) 2001ZHA/LIY (2) 2003ZHA/ARM(b)

PtC–CH –CH2

(1) 128.2G2.3 (1) 110.7G0.7 (2) O111 (3) 115G4 (4) 112.5 (1) 61.6G1.8 (1) 40.8G1.8

536.4G9.6 463.1G2.9 O464 481G17 471 257.6G7.7 170.8G7.7

Ion reactions

(1) 2001ZHA/LIY

(1) 55 (2) 54.9

230.1 229.7

(1) Review (2) PD

–CH3 –CH4

PtC–C2H4

(2) 1991IRI/BEA (3) 1994WES/SCH (4) 1997PAV/BLO

(1) 1998SCH/SCH (2) 2004STR/CIT (continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

964

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.2 (continued) BDEs of PtC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

PtC–Si

123G12

515G50

Derived

1974GUR/KAR

PtC–B

95G25

398G105

Derived

1974GUR/KAR

(1) (2) (3) (3) (4)

322 %309 318.4G6.7 295.2G6.7 314

(1) FT ICR (2) Spectra. (3) Ion reactions

(1) 1997PAV/BLO (2) 2003THO/STR (3) 2003ZHA/ARM

(4) Derived

(4) 2000SCH/SCH

PtC(O)x–O xZ0

1

77 %73.9 76.1G1.6 70.6G1.6 75

PtC(CO)–O

74.0G2.8

309.7G11.6

Ion reactions

2003ZHA/ARM

PtC–O2

15.4G1.2

64.6G4.8

Ion reactions

2003ZHA/ARM

(1) (2) (1) (1) (1)

212.3G9.6 218.1G8.7 193.0G9.6 98.4G4.8 53.1G4.8

CID

(1) 2001ZHA/ARM (2) 2003ZHA/ARM(b)

PtC(CO)x–CO xZ0 1 2 3

50.7G2.3 52.1G2.1 46.1G2.3 23.5G1.2 12.7G1.2

PtC(O)–CO

51.0G2.3

213.2G9.6

Ion reactions

2003ZHA/ARM

PtC–CO2

14.3G1.2

59.8G4.8

Ion reactions

2003ZHA/ARM(b)

PtC–N –N2 –NO

78.1G2.3 6.2G2.3 72.2G2.3

326.9G9.6 26.1G9.6 302.0G9.6

GIB MS

2004ZHA/ARM

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

BDEs of Ni(NiG)–, Pd(PdG)–, and Pt(PtG)–X Bonds PtC(NH3)x–NH3 xZ0 1 2 3

65.5G2.8 62.4G2.3 18.4G1.2 11.0G0.9

274G12 261G10 77G5 46G4

965

CID

2003LIY/STY

20.3.3 PtK–X bonds Table 20.3.3 BDEs of PtL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) PtK(Pt)x–Pt xZ0

kcal/mol

N

PtK 2 –CO

13.8

57.9

PES

2002LUT/PON

(1) (2) (1) (2) (3) (1) (2) (3) (1) (2) (1) (2) (1) (2) (3) (2)

215G30 220G30 203G50 220G50 270G13 189G17 220G22 206G14 82G10 102G14 90G14 109G19 140G19 180G30 166G14 174G14

(1) CID (2) CID

(1) 1995GRU/ERV (2) 1997GRU/ERV

(3) PD

(3) 2001SHI/SPA

2 3

PtK 3 ðCOÞx –CO xZ0 1

2

3 4 5

6

51.4G7.2 52.6G7.2 48.5G12 52.6G12 64.5G3.1 45.2G4.1 52.6G5.3 49.2G3.3 19.6G2.4 24.4G3.3 21.5G3.3 26.1G4.5 33.5G4.5 43.0G7.2 39.7G3.3 41.5G3.3

284.5G2.9 306.7 425G39 425 494 415 487 473 w510

References

(1) (2) (2) (3) (2) (3) (2) (3) (4)

1

68.0G0.7 73.3 101.5G9.2 101.6 118.1 99.2 116.5 113 w122

kJ/mol

Methods (reference in parentheses) (1) PES (2) Re-cal.

(1) 1993HO/POL (2) 1997GRU/ERV

(3) Review

(3) 2001ARM

(4) Extrapolate

(4) This volume

(continued)

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

966

Comprehensive Handbook of Chemical Bond Energies

Table 20.3.3 (continued) BDEs of PtK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

PtK 3 ðCOÞx –2CO xZ2 3 4

71.5G6.9 52.8G4.6 68.5G5.6

299G29 221G19 287G24

CID

1997GRU/ERV

PtK 3 ðPtÞx –CO xZ3 4 5

60.0G9.2 57.7G9.2 53.0G6.9

251G39 241G39 222G29

CID

1997GRU/ERV

PtK 4 ðCOÞ7 –CO PtK 5 ðCOÞ8 –CO

18.4G6.9 18.4G6.9

77G29 77G29

CID

1997GRU/ERV

PtK 2 ðCOÞ–Pt PtK 2 –PtCO PtK(PtCO)–PtCO

%69.2G9.2 %78.2G4.8 %65.5G5.8

%289G39 %327G20 %274G24

CID

1997GRU/ERV

PtK(Pt)2(CO)6–Pt(CO)2 %32.3G9.2

%135G39

CID

1997GRU/ERV

PtK K–C2 H

222

PES

2000MOR/JAR

53

7366—CHAPTER 20—3/2/2007—11:35—SHANMUGAM—15376—XML MODEL B – pp. 903–966

chapter twenty-one

BDEs of Cu(Cu G )–, Ag(Ag G )–, and Au(AuG)–X bonds 21.1 Cu–, CuC–, and CuK–X bonds 21.1.1 Cu–X bonds Table 21.1.1 BDEs of Cu–X Bonds

The broken bonds (boldfaceZdissociated fregment) Cu–Cu

Cu(Cu)x–Cu xZ1

2

3

4

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

References

(1) 46.8 (2) 47.9G3.9 (3) 41.7G3.2 (4) 46.6G1.2 (5) 48.0

195.7 200.4G16.4 174.6G13.5 195.0G5.2 201

(1) Review (2) Derived (3) CID (4) MS (5) Review

(1) 1996SMI/YAT (2) 2000SPA/LEE (3) 2000ING/BUS (4) 2001HIL (5) 2001ARM

(1) 25.8 (2) 26.5G4.6 (3) 17.5G5.3 (4) 26.5 (5) 22.1 (2) 62.7G4.6 (3) 46.8G17.5 (4) 62.6 (5) 54.9 (2) 42.7G3.9 (3) 36.6G18.0 (4) 42.5 (5) 39.7 (2) 59.0G7.4 (3) 41.5G17.8 (4) 59.0 (5) 50.3

108 111G19.3 73G22 111 92.6 262.4G19.3 196G73 262 230 178.5G16.4 153G75 178 166 247G31 174G74 247 210

(1) Review (2) CID (3) MS (4) Review (5) Derived

(1) 1986MOR (2) 2000ING/BUS (3) 2001HIL (4) 2001ARM (5) 2004JAQ/LAB

(continued)

967

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Table 21.1.1 (continued) BDEs of Cu–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fregment) 5

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 61.4G10 (3) 24.2G18.2 (4) 61.4 (5) 42.9 (2) 68.8G8.1 (3) 23.1G11.1 (4) 68.8 (5) 59.3 (3) 23.5G11.5 (5) 23.5 (6) w71.8

257G42 101G76 257 180 288G34 97G46 288 248 98G48 98.4 w300

(6) Extrapolate

(6) This volume

Cu(100, surf.)–Cu

(1) 9.2 (phys) (2) 9.0G1.4 (3) 6.5G1.4 (4) 8.8 (5) 8.3G0.7

38.6 37.6G5.8 27.0G5.8 36.7 34.7G2.9

(1) Scattering (2) LEIS (3) Scattering (4) LEIS (5) LEED

(1) (2) (3) (4) (5)

Cu(100, surf.)–Cu

18.4G0.7 (phys)

77.2G2.9

STM

1998KLU/HAN

Cu(100, surf.)–Cu

69

289

Review

1995SEE/ALL

Cu(111, surf.)–Cu

(1) 10.4G0.5 (phys) (2) 5.1G0.5 (3) 5.2G0.2

43.4G1.9 21.2G1.9 21.6G0.9

STM

(1) 1998KON/IBA (2) 1999SCH/VER (3) 1999GIE/IBA

Cu(111, surf.)–Cu

17.5G0.9 (phys)

73.3G3.9

STM

1999GIE/KON

Cu–Cu bond in dicopper (II) cryptates

47.8

200

Electrochemical

2004COY/DOW

Cu–Ag

(1) 41.6 (2) 41G2 (3) 41.0G2.3

174.1 172G8 171.5G9.6

(1) MS (2) Review (3) Spectroscopy

(1) 1960ACK/STA (2) 1970DAR (3) 1991BIS/MAR

Cu(100, surf.)–Ag

17.5G3.7 (phys)

73.3G15.4

Oxidation

1973ROU

6

7 N

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

1987MIG/SAN 1992BRE/BOE 1992ERN/FAB 1994BRE/BAK 1994DUR/WEN

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

969

Cu(100, surf.)–Ag

65

272

Review

1995SEE/ALL

Cu(111, surf.)–Ag

17.5G3.7 (phys)

73.3G15.4

Oxidation

1973ROU

Cu–Au

(1) 55.4 (2) 54.9G2.3 (3) 54.3G0.3

231.8 229.7G9.6 227.1G1.2

(1) MS (2) Review (3) Spectrometry

(1) 1960ACK/STA (2) 1986MOR (3) 1993BEH/ARR(b)

Cu–Li

(1) 46.1G2.1 (2) 45.9

192.9G8.8 191.9

(1) MS (2) R2PI

(1) 1974NEU/ZMB(b) (2) 1997BRO/KNI

Cu–Na

42.1G4

176.1G16.7

MS

1973PIA/GIN

Cu(100, surf.)–Na

(1) 1.18G0.14 (phys) (2) 1.21G0.20 (3) 1.23G0.02

4.92G0.58

HAS

(1) 1993ELL/TOE

5.07G0.09 5.13G0.09

Cu(100, surf.)–Na

21

88

Review

1995SEE/ALL

Cu(100, surf.)–K

23G2.3

96G9.6

HAS

1994REI/GRA

Cu–Tb –Dy –Ho

45.7G4.3 34.4G4.3 34.4G4.5

191G18 144G18 144G19

MS

1989CHA/GIN

Cu(cryst.)–Ti

46.4G0.8

193.9G3.4

Ion-beam

1998ALM/MAC

Cu–Cr

(1) 36.9G6 (2) 37.8G3.5

154.4G25.1 158.2G14.5

(1) MS (2) Review

(1) 1970KAN/STR (2) 1986MOR

Cu(cryst.)–Cr –Mn –Fe

46.4G0.8 45.9G0.5 47.0G0.5

193.9G3.4 192.0G1.9 196.8G1.9

Ion-beam

1998ALM/MAC

(2) 1997GRA/HOF (3) 2001ELL/GRA

(continued)

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

970

Comprehensive Handbook of Chemical Bond Energies

Table 21.1.1 (continued) BDEs of Cu–X Bonds

The broken bonds (boldfaceZdissociated fregment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

Cu–Co

(1) 38.0G5 (2) 38.5G3.9

159.0G20.9 161.1G16.4

(1) MS (2) Review

(1) 1970KAN/STR (2) 1986MOR

Cu–Ni

(1) 47.4G5 (2) 48.9G5.8 (3) 48.2G2.3

198.3G20.9 204.6G24.3 201.7G9.6

(1) MS (2) Review (3) Spectrometry

(1) 1970KAN/STR (2) 1986MOR (3) 1989FU/MOR

Cu(cryst.)–Ni

53.5G0.6

223.8G2.4

Ion-beam

1996ALM/MAC

Cu(100, surf.)–Hg

w12

w48

HAS

1992LI/LIN

Cu(crystal)–B

26.5G2.3

111.0G9.6

NMR

2001FUL/ITT

Cu–Al

54.3G0.3

227.1G1.2

Spectroscopy

1993BRH/ARR(b)

Cu–Ga

51.6G3.6

215.9G15

MS

1972CAR/BER

Cu–In

44.8G1.9

187.4G7.9

MS

1989BAL/NUN

Cu(100, surf.)–He

0.22

0.94

HAS

1980LAP/LEJ

Cu(110, surf.)–He

(1) 0.14 (2) 0.15

0.60 0.61

HAS

(1) 1982HAR/LIE (2) 1984GOR/SAL

Cu(311, surf.)–He

0.15

0.61

HAS

1982PER/LAP

Cu(110, surf.)–Ne

0.29

1.20

Review

1991VID/IHM

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References

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

971

Cu(100, surf.)–Ar

2.9

12.0

Scattering

1980LAP/LEJ

Cu(110, surf.)–Kr

(1) 3.0G0.1 (2) 2.6

12.6G0.4 11.0

LEED

(1) 1982GLA/JAU (2) 2000SHY/CAR

Cu(111, surf.)–Kr

2.7

11.5

Review

1991VID/IHM

Cu(100, surf.)–Xe

4.5

18.9

AES

1979GLA/BAR

Cu(110, surf.)–Xe

(1) 4.6G0.1 (2) 5.2 (3) 5.0

19.2G0.4 21.8 21.0

(1) AES (2) Scattering (3) TDS

(1) 1982GLA/JAU (2) 1994RAM/GIR (3) 1998POU/RAM

Cu(110, 2x1/O, surf.)–Xe

5.4

22.5

TDS

1998POU/RAM

Cu–H

(1) 58.3G2 (2) 65.5 (3) 61.6G4.2 (4) 60.9G1.4

243.9G8.4 274.0 257.6G17 254.8G6

(1) MS (2) Spectroscopy (3) GIB MS (4) GIB MS

(1) 1979KAN/MOO (2) 1981RAO/RAO (3) 1990FIS/ARM (4) 1996ARM/KIC

Cu–D

64.6

270.3

Spectroscopy

1979HUB/HER

Cu(polycr. surf.)–H

57.0

238.5

Isotherm

1972ALE/PRI

Cu(100, surf.)–H

(1) w56 (2) !60

w234 !251

(1) Review (2) TPD

(1) 1979ERT (2) 1989ANG/WIN

Cu(110, surf.)–H

!58

!243

TPD

1989ANG/WIN

Cu(111, surf.)–H

(1) 56 (2) !60

234 !251

(1) Review (2) TPD

(1) 1979ERT (2) 1989ANG/WIN

(continued)

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

972

Comprehensive Handbook of Chemical Bond Energies

Table 21.1.1 (continued) BDEs of Cu–X Bonds

The broken bonds (boldfaceZdissociated fregment) Cu(311, surf.)–H

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

56.4

236

Review

1988CHR

(1) 98.8G3 (2) 102.8 (3) 96.8G0.7 (4) 99.0 (5) 102.9G1 (6) 87.6

413.3G12.6 430.1 405.2G2.9 414.0 430.6G4.2 366.5

(1) MS (2) Review (3) CL (4) CL (5) Derived (6) MS

(1) (2) (3) (4) (5) (6)

1977EHL/WAN 1979HUB/HER 1992BAL/HAR 2003SAD/KOW 2005HIL 1966KEN/MCD

Cu–Cl

(1) 90.6G1.1 (2) 91.5 (3) 90.3G1.8 (4) 90.3

379.1G4.6 382.8 377.8G7.5 377.8

(1) MS (2) Review (3) MS (4) MS

(1) (2) (3) (4)

1972GUI/GIG 1979HUB/HER 1996HIL/LAU 2005HIL

Cu–Br

(1) 79G6 (2) 80 (3) 79.8

331G25 334.7 333.9

(1) Review (2) Review (3) MS

(1) 1968GAY (2) 1979HUB/HER (3) 2005HIL

Cu–I

(1) 47G5 (2) 69G15 (3) !76.3 (4) 70.0

197G21 289G63 !319.2 292.9

(1) Review (2) Review (3) Review (4) MS

(1) (2) (3) (4)

1968GAY 1974GUR/KAR 1979HUB/HER 2005HIL

Cu–O

(1) 65.2G3.5 (2) 64.3G4.6 (3) 65.7G3.5 (4) 61.9G7.2 (5) 68.7G2.8

272.8G14.6 269G19.3 275G14.5 259G30 287.4G11.6

(1) MS (2) Spectrometry (3) HT MS (4) HT MS (5) GIB MS

(1) (2) (3) (4) (5)

1972SMO/MAN 1989MER 1993WAT/THI 1993WAT/THI 1999ROD/WAL

Cu(foil)–O

103

431

Review

1991BEN

Cu(100, surf.)–O

108.2

452.7

Review

2003ZEI

Cu(110, surf.)–O

(1) 89 (2) 111.2

372 465.3

Review

(1) 1991BEN (2) 2003ZEI

Cu(F)x–F xZ0

1

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BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

973

Cu(111, surf.)–O

103.0

431.0

Review

2003ZEI

Cu–S

65.6G3.5

274.5G14.6

MS

1972SMO/MAN

Cu(100, surf.)–S

92

385

Review

1982BAR/AGR

Cu(111, surf.)–S

6 (phys)

25

HAS

1991HIN/FRE

Cu(111, surf.)–S

(1) 97 (2) 46

406 192

Review

(1) 1982BAR/AGR (2) 1995SEE/ALL

Cu–Se

61.0G3.5

255.2G14.6

MS

1972SMO/MAN

Cu–Te

(1) 55.1G3.5 (2) 66.6

230.5G14.6 278.7

MS

(1) 1972SMO/MAN (2) 1976ABB/AZI

Cu(100, surf.)–N

120.8

505.4

Review

2003ZEI

Cu(110, surf.)–N

(1) 135 (2) 124.2

565 519.7

Review

(1) 1991BEN (2) 2003ZEI

Cu(111, surf.)–N

115.0

481.2

Review

2003ZEI

Cu–Si

52.9G1.5

221.3G6.3

MS

1981RIE/LAM

Cu–Ge

(1) 48.8G5 (2) 49.9G5

204G21 208.8G21

MS

(1) 1968KAN/STR (2) 1972NEC/SOD

Cu–Sn

(1) 41.4G4 (2) 40.6G2.4

173.2G16.7 170G10

MS

(1) 1962ACK/DRO (2) 1978KIN/DUF

Cu(100,surf.)–Pb

(1) 15.7 (phys) (2) 13.1

65.7 55.0

(1) Scattering (2) STM

(1) 1993COH/GIB (2) 2001COH/PRE

(continued)

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

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Comprehensive Handbook of Chemical Bond Energies

Table 21.1.1 (continued) BDEs of Cu–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fregment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Cu(100,surf.)–Pb

70

293

Review

1995SEE/ALL

Cu(110, surf.)–Pb

13.1 (phys)

55.0

STM

2001COH/PRE

Cu–H2

O22G5

O92G21

Est. by exp.

1987TEW/FRE

Cu(polycs. surf.)–H2

(1) 11.2G0.6 (2) 9.6–10.3 (3) 9.6–12 (4) 12.3G1.4 (5) 14.1G1

47G2.5 40–43 40–50 51.5G6 59G4

(1) H2 conversion (2) H2 conversion (3) S.P. (4) Isotopic (5) Ox-Red

(1) (2) (3) (4) (5)

Cu(100, surf.)–H2

(1) 0.5 (phys) (2) 0.59

2.1 2.46

Scattering

(1) 1983LAP/PER (2) 1988AND/WIL

Cu(100, surf.)–H2

(1) 13.5 (2) 11.4G0.2

56.5 48G1

(1) Conversion (2) TPD

(1) 1968VOL/JUN (2) 1993RAS/HOL

Cu(110, surf.)–H2

0.51 (phys)

2.12

Scattering

1981GLA/JAU

Cu(110, surf.)–H2

14.3G1.4

59.8G5.9

Kinetics

1991CAM/DOM

Cu(111, surf.)–H2

0.74 (phys)

3.01

Review

1991VID/IHM

Cu(111, surf.)–H2

(1) 9.1 (2) 9.2

38.1 38.6

(1) Conversion (2) TDS

(1) 1968VOL/JUN (2) 1999KAM/KUP

Cu(100, surf.)–D2

(1) 0.62 (phys) (2) 0.75

(1) 2.6 (2) 3.1

Scattering

(1) 1988AND/WIL (2) 1997BER/ART

Cu(100, surf.)–D2

13.4

56

TPD

1993RAS/HOL

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

1956RIE/VOR 1957ELE/ROS 1972ALE/PRI 1974KIY/MOM 1987GAB/KUR

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

975

Cu(111, surf.)–D2

(1) 16 (2) 8.1

66.9 33.8

TDS

(1) 1996LEE/POK (2) 1999KAM/KUP

Cu(100, surf.)–Cl2

33.2

138.9

MS

1985WIN

Cu–O2

15G7

63G29

Kinetics

1992MIT

Cu(plate, surf.)–O2

5.2 (phys)

21.8

Calorimetry

1964HAY/TRA

Cu(polycr. surf.)–O2

(1) 109.7 (2) 78

459 326

(1) Calorimetry (2) Review

(1) 1969MUR/VAS (2) 1982RAO/KAM

Cu(110, surf.)–O2

53

222

TD

1967ERT

Cu2O(polycr. surf.)–O2

62

259

Review

1964HAY/TRA

Cu(111, surf.)–O2

4 (phys.)

17

Ellipsometry

1979HAB/KIE

Cu–OH

O97

O406

FT–MS

1985WEI/WIL

Cu(111, surf.)–OH

71.5

299

Adsorption

1993HER/WIT

Cu–CO

6G1.2

25G5

LP

1991BLI/MIT

Cu(polycr. surf.)–CO

(1) 9.3 (2) 18–20 (3) 13.9G0.3

39 75–84 58.2G1.4

(1) Isothermal (2) IR (3) TDS

(1) 1953TRA (2) 1967KAV/SOK (3) 2001VOL/WIT

Cu(100, surf.)–CO

(1) 2–3 (phys) (2) 0.74 (3) 0.71G0.23

8–13 3.09 3.00G0.96

(1) LITD (2) HAS (3) HAS

(1) 1982VIS/BUR (2) 1996HOF/TOE (2) 1998GRA/HOF

(continued)

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

976

Comprehensive Handbook of Chemical Bond Energies

Table 21.1.1 (continued) BDEs of Cu–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fregment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Cu(100, surf.)–CO

(1) 13.5 (2) 16.7 (3) 12.2G0.3

56.5 69.9 51.1G1.4

(1) LEED (2) IRAS (3) TDS

(1) 1972TRA (2) 1992TRU/ROD (3) 2001VOL/WIT

Cu(110, surf.)–CO

2.24G0.9 (phys)

9.36G0.39

STM

1997BRI/DOE

Cu(110, surf.)–CO

(1) w13.1 (2) 16.7 (3) 14.6 (4) 12.9G0.3

w55 70 61 54.0G1.4

(1) TPD (2) IRAS (3) TPD (4) TDS

(1) (2) (3) (4)

1977HOR/HUS 1978MAD/BEN 1996AHN/MOC 2001VOL/WIT

Cu(111, surf.)–CO

(1) 12 (2) 9.6 (3) 13.2 (4) 12.2 (5) 11.3G0.3

50 40 55.2 51.0 47.3G1.4

(1)IRAS (2) TDS (3) Mol. beam (4) TPD (5) TDS

(1) (2) (3) (4) (5)

1979HOL/PRI 1986KIR/KRU 1990HIN/DUB 1994BON/KIS 2001VOL/WIT

Cu(211, surf.)–CO Cu(221, surf.)–CO

14.0G0.3 13.8G0.3

58.4G1.4 57.7G1.4

TDS

2001VOL/WIT

Cu(311, surf.)–CO

(1) 9.3G0.5 (2)14.5G0.5

39G2 61G2

(1) IR (2) LEED

(1) 1975PRI/CAT (2) 1975PAP/PRI

Cu(332, surf.)–CO

10.3 (phys. a1 state) 43 12.2 (a2 state) 51

TDS

1995BON/KIS

Cu(332, surf.)–CO

16.0

67

TDS

1995BON/KIS

Cu(532, surf.)–CO

13.6G0.3

56.8G1.4

TDS

2001VOL/WIT

CuCl(111, surf.)–CO

23

96

PES

1993SOL/JON

SiO2/Cu–CO

w17

w71

IR

1993XU/GOO

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

977

Pt(111, surf.)Cu–CO

15.8–17.0

66–71

TDS

1983SHE/STE

Cu(surf.)Cu–CO

12.6–13.5

53–56

TDS

1983SHE/STE

Cu2O(polycs. surf.)–CO

20

84

Review

1964HAY/TRA

Ru(1000, surf.)Cu–CO

17.1

71.4

Mol. beam

1999KNE/GEM

[CuI(tmpa)(CO)]C tmpaZtris(2-pyridymethyl)amine

10.4

43.6

TR–IR

2005FRY/COH

Cu(100, surf.)–CO2

22.2G1.2

93G5

TPD

1992TAY/RAS

Cu(110, surf.)–CO2

6.3G0.3

26.4G1.3

TR–EELS

1990ELL/WU

Cu(100, surf.)–H2O

10.1

42.4

TPD

1984SEX/HUG

Cu(110, surf.)–H2O

(1) 10–12.5

42–52

(1) Review

(1) 1987OUT/MAD(b)

(2) 13.2

55.2

(2) Spectroscopy

(2) 1992HIN/DUB

Cu(111, surf.)–H2O

9.8

41.0

Kinetics

1987CAM/DAU

Cu2O(polycs. surf.)–SO2

37

155

Review

1964HAY/TRA

Cu–CH3

Cu(110, surf.)–CH2 Cu(110, surf.)–CH3

(1) O59

O247

(1) FT–MS

(1) 1985WEI/WIL

(2) 58G2 (3) 53.3G1.2

242.7G8.4 223G5

(2) GIB MS (3) GIB MS

(2) 1989GEO/FIS (3) 1996ARM/KIC

75G10 33G8

314G42 138G33

AES/TPRS

1992CHI/WEN

(continued)

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

978

Comprehensive Handbook of Chemical Bond Energies

Table 21.1.1 (continued) BDEs of Cu–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fregment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Cu(111, surf.)–CH3

w29

w121

AES/TPR

1993LIN/BEN

Cu(100, surf.)–HC(O)O Cu(110, surf.)–HC(O)O

28.1 24.9

117.7 104.1

Re-cal.

2006WAN/MOR

Cu(111, surf.)–HC(O)O

17.1

71.4

Re-cal.

2006WAN/MOR

Cu(100, surf.)–CH4

3.8 (phys)

15.9

HAS

1997GRA/BER

Cu(110, surf.)–CH3Cl

8–10

33–42

TPD

1991MAG/GEB

Cu(111, surf.)–CH3I

w8.5

w35.5

AES/TPR

1993LIN/BEN(b)

Cu(100, surf.)–CH3OH

10.0

41.8

TPD

1984SEX/HUG

Cu(110, surf.)–CH3OH

16.7 (phys)

70

FDS

1978WAC/MAD

Cu(110, surf.)–CH3OH

30.9G0.2

129.3G0.8

FDS

1978WAC/MAD

Cu(polycs. surf.)–C2H2

19

79

Review

1964HAY/TRA

Cu(100, surf.)–C2H2

(1) 6G1.2 (phys) (2) 12.2G0.2

25G5 51.1G1.0

(1) Photolysis (2) STM

(1) 1991BLI/MIT (2) 1999LAU/HO

Cu(110, surf.)–C2H2

22

92

TPD

1983OUT/FRI

Cu(polycs. surf.)–C2H4

18

75

Review

1964HAY/TRA

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

979

Cu(110, surf.)–C2H4

8.6 (phys)

36.2

HAS

1997GRA/BER

Cu(110, surf.)–C2H4

13

54

TPD

1983OUT/FRI

Cu2O(polycs. surf.)–C2H4 20

84

Review

1964HAY/TRA

Cu(100, surf.)–C2H6

6.0 (phys)

25.1

HAS

1997GRA/BER

Cu(111, surf.)–C2H2

1.2 (phys)

5.0

EELS

1984BAN/CHE

Cu(111, surf.)–C2H4

0.2 (phys)

0.6

Combined

1998FUH/WAC

Cu(100, surf.)–C2H3Cl Cu(100, surf.)–ClHCHCl

7–11 7–11

29–46 29–46

TPD

1997YAN/KAS

Cu(111, surf.)–C2H5

13.2–15.1

55–63

TPD

2001ZAE

Cu(111, surf.)–C2H6

0.2 (phys)

0.6

Combined

1998FUH/WAC

Cu(111, surf.) –CH2ClCH2Cl

12.4G1

52G4

LEED

1992WAL/JON

Cu(100, surf.)–C2H5OH

11.4

47.5

TPD

1984SEX/HUG

Cu(100, surf.) –CH3COCH3

10.1

42.4

TPD

1984SEX/HUG

Cu(110, surf.) –CH3COCH3

9

38

TPD

2000LEE/AHN

Cu(111, surf.)–c-ether trixane

14.1

59

TPD

1994HOF/WEG

5.9G0.9

24.7G3.8

TPD

1995MEY/GEL

Cu(111, surf.) –CH3CHCH2

(continued)

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

980

Comprehensive Handbook of Chemical Bond Energies

Table 21.1.1 (continued) BDEs of Cu–X Bonds

The broken bonds (boldfaceZdissociated fregment) –CFH2CHCH2 –CF3CHCH2 –CF3CHCF2 –CF3CFCF2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

5.5G0.6 8.1G0.9 9.0G1.5 8.0G0.4

23.0G2.5 33.9G3.8 37.7G6.3 33.5G1.7

10.1

42.4

TPD

1984SEX/HUG

12.6 13.9

52.9 58.0

TPD

1984SEX/HUG

Cu(100, surf.)– C2H5OC2H5

10.7

44.9

TPD

1984SEX/HUG

Cu(100, surf.)–n-C5H12 –n-C6H14

10.4 12.0

43.7 50.4

TPD

1984SEX/HUG

Cu(100, surf.)–n-C7H16 –n-C8H18 –n-C9H20 –n-C10H22

13.6 14.6 16.2 17.9

57.1 61.0 67.6 74.8

TPD

1984SEX/HUG

Cu(110, surf.)–nC7H16 –nC8H18 –nC10H22

w11.1 w14.1 w15.9

w46.3 w58.9 w66.6

HAS

1997GRA/BER

Cu(110, surf.)–c-C6H12

w10.1

w42.5

HAS

1997GRA/BER

Cu(C6H6)x–C6H6 xZ0 1

3.9G3 6.5G4.6

16.4G12.5 27.0G19.3

Derived

TAK/TAK

Cu(110, surf.)–C6H6

w10.8

w45.3

HAS

1997GRA/BER

Cu(100, surf.) –n-CH3CCN

Cu(100, surf.) –n-C3H7OH –n-C4H9OH

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BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

981

Cu(111, surf.)–C6H6

!14.3

!60

TPD/EELS

1994XI/YAN

Cu(111, surf.)–C6H5I

11.3G1.5

47.3G6.3

TPRS

1992XI/BEN

C–H bond broking Cu(110,8!2, surf.) –C6H5COOH

81

339

HR–EELS

1998CHE/FRE

Cu–methylacetylene –dimethylacetylene

7.6G1.4 8.6G1.4

32G6 36G6

Kinetics

1993BLI/MIT(b)

Cu(L)x–L, LZTMEZ tetramethylethylene xZ0 1

10G1.4 18G2.4

42G6 75G10

Kinetics

1993BLI/MIT

(1) %11 (2) 11.2G3.6 (3) 11G4 (2) 20G1 (3) 11G2

%46 47G15 46G19 83.7G4.2 46G8

(1) PD (2) Derived (3) Derived

(1) 1996MIT/LIA (2) 2003MIY/SUG (3) 2005LI/SOH

Cu(100, surf.)–NH3

(1) 13.6 (2) 17.8

56.9 74.3

(1) TR EELS (2) TPD

(1) 1991WU/KEV (2) 1997MOC/AHN

Cu(surf.)–(CN)2

12.9

54

TPD/PES

1983OUT/JOR

Cu(110, surf.)–pyridine

22.4

93.6

TDS

2000LEE/AHN

Cu(110, surf.)–DC –HtBDC DCZdecacyclene, HtBDCZhexa-di-tertbutyl-decacyclene

17.1G0.7 13.1G0.5

71.4G2.9 55.0G1.9

Review

2003ROS/SCH

Cu(Cu)x–NH3 xZ0

1

7366—CHAPTER 21—5/2/2007—08:21—CRCPAG—15377—XML MODEL B – pp. 967–1026

982

Comprehensive Handbook of Chemical Bond Energies

21.1.2 CuC–X bonds Table 21.1.2 BDEs of CuD–X Bonds

The broken bonds (boldfaceZdissociated fregment) CuC–Cu

CuC(Cu)x–Cu xZ1 2 3 4 5 6 7 8 10 11 12 13 14 15 16 17 18 19 20 21 22 23 N

CuC(Cu)x–Cu2 xZ0 1 2 3 4

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(1) 43.3G1.8 (2) 42.4 (3) 37.8G3.2 (4) 37.1G1.8

181.2G7.7 177.4 158.2G13.5 155.2G7.7

(1) (2) (3) (4)

(1) 65.7G5.1 (1) 15.7G2.8 (2) 24.4G1.2 (1) 56.3G4.6 (1) 21.9G3.5 (2) 47.5G2.5 (1) 48.4G5.8 (2) 71.7G3.7 (1) 25.6G5.8 (2) 66.0G3.5 (1) 38.3G6.5 (2) 84.4G4.2 (2) 47.0G7.1 (2) 67.6G4.8 (2) 78.9G5.3 (2) 76. 6G6.7 (2) 87.2G6.7 (2) 72.2G5.8 (2) 81.6G5.5 (2) 86.0G5.8 (2) 92.2G5.8 (2) 89.0G5.5 (2) 96.6G5.5 (2) 75.4G4.4 (2) 82.8G4.8 (2) 78.9G4.6 (2) 84.9G4.8 (3) w71.8

275G21 65.6G11.6 102.3G4.8 235G19 91.7G14.5 198.8G10.6 203G24 300G15.4 107G24 276G14.5 160G27 353G17.4 196.8G29.9 282.7G20.2 330.0G22.2 320.3G28.0 364.7G28.0 302.0G24.1 341.6G23.2 359.9G24.1 385.9G24.1 372.4G23.2 404.3G23.2 315.5G18.3 346.4G20.2 330.0G19.3 355.1G20.3 w300

CID

(3) Extrapolate

(3) This volume

(1) 61.6G5.3 (2) 65.3G3.2 (1) 83.7G12.7 (1) 24.7G4.2 (2) 45.9G2.3 (1) 76.8G17.3 (1) 35.5G6.0

258G22 273G13.5 350G53 103G17 192G9.6 321G72 149G25

CID

(1) 2000ING/BUS (2) 2001KRU/SCH

R2PI Derived CID CID

References (1) (2) (3) (4)

1989SAP/HAR 1996SMI/YAT 2000ING/BUS 2001KRU/SCH

(1) 2000ING/BUS (2) 2001KRU/SCH

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

5 6 8 12 13 14 15 16 17 18 19 20 21

(1) (1) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2)

77.9G14.3 63.9G8.8 63.9G6.5 61.1G9.5 64.8G5.1 81.4G6.5 73.8G4.6 89.4G5.3 79.8G5.8 85.1G6.2 67.3G8.3 71.9G5.1 74.3G5.3

983

326G60 267G37 267G27 256G40 271G21 341G27 309G19 374G22 334G24 356G26 282G35 301G21 311G22

CuC–Fe

(1) 53G7 (2) O52

222G29 O218

(1) PD (2) Ion reactions

1987HET/FRE

CuC–Kr

5.8G0.2

24.3G0.8

HP MS

1989ELS/SCH

CuC–Ar

(1) 13.1 (2) 12.4G1.6

54.9 51.9G6.8

(1) GDMS (2) CID

(1) 1995BAR/SMI (2) 2002KOS/SCH

CuC–Xe

24.4G1.4

102.1G5.8

CID

2002KOS/SCH

CuC–H

22.2G3

93G13

GIB MS

1986ELK/ARM

CuC–F

(1) 64G8 (2) 28.1G5

268G34 117G21

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

CuC–Cl

21.7G2.4

91G10

Derived from IP in ref.

1996NIST

(1) (2) (1) (2) (1) (2)

64.4G4.2 51.9G0.4 69.9G4.2 42.3G0.8 36.8G2.1 20.5G0.8

Equilibrium

(1) 1998KEM/WEI (2) 2002MAN/BUS

CuC(H2)x–H2 xZ0 1 2

15.4G1.0 12.4G0.1 16.7G1.0 10.1G0.2 8.8G0.5 4.9G0.2

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

984

Comprehensive Handbook of Chemical Bond Energies

Table 21.1.2 (continued) BDEs of CuC–X Bonds

The broken bonds (boldfaceZdissociated fregment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(1) 5.1G0.6 (2) 3.8G0.2 (1) 1.0G0.2 (2) 2.1G0.1 (1) 1.0G0.3

21.3G2.5 15.9G0.8 4.2G0.8 8.8G0.04 4.2G0.8

CuC–CH2

(1) 61.3G1.2 (2) 63.9G1.6

256.6G5 267.3G6.8

GIB MS

(1) 1986ELK/ARM (2) 1990FIS/ARM

FeCuC–CH2

O79

O331

FT–MS

1987TEW/FRE

CuC–CH3

(1) 29.7G1.7 (2) 26.5G1.6

124G7 111G7

GIB MS

(1) 1989GEO/FIS (2) 1996ARM/KIC

CuC–CH2O

34.7G2.3

145G10

Review

1996ARM/KIC

CuC–C2H2

(1) O26.1G2.5 (2) O5.1G2.3

O109G11 21.2G9.6

(1) GIB MS (2) Revised

(1) 1990FIS/ARM (2) 1994FIS/ARM

(1) 44–50 (2) 42.0G3.2 (3) 45 (1) 41.5G3.0

184–209 176G14 188.3 174G13

(1) GIB MS (2) GIB MS (3) Review

(1) 1996HER/KOC (2) 1998SIE/JAR (3) 1998SCH/SCH

CuC–CH2CHCHCH2

!53

!222

FT-MS

1987TEW/FRE

FeCuC–CH2CHCHCH2 CuC–(CH3)2CHCH2CH3 FeCuC–(CH3)2CHCH2CH3 FeCuC–CH2CHCHCHCH3

O29 !53 O28 O26

O121 !222 O117 O109

FT–MS

1987TEW/FRE

CuC–(CH3)2CHCH(CH3)2

O53

O222

FT–MS

1987TEW/FRE

3 4 5

CuC(C2H4)x–C2H4 xZ0

1

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

References

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds FeCuC–(CH3)2CHCH(CH3)2 FeCuC–cyclopenta-1,3-diene

985

O26 O24

O109 O100

(1) (2) (3) (4) (4)

%222 209 %191 218.0G9.6 155.3G11.6

(1) FT–MS (2) PD (3) PD (4) CID

(1) 1987TEW/FRE (2) 1987HET/FRE (3) 1992WIL/YEH (4) 1995MEY/KHA

O21 O53

O88 O222

FT–MS

1987TEW/FRE

O46

O192

O53

O222

CuC–O

(1) 25–40 (2) 38.3G3.5 (3) 32.0G2.8

105–167 160.2G14.6 133.9G11.6

(1) ICR (2) CID (3) CID

(1) 1981KAP/STA (2) 1990FIS/ELK (3) 1999ROD/WAL

FeCuC–O

O85

O356

FT–MS

1987TEW/FRE

CuC(CO)x–CO xZ0 1 2 3

35.6G1.7 41.1G0.7 17.9G1.0 12.7G0.7

149G7 172G3 75G4 53G3

CID

1995MEY/CHE

(1) 6.2 (2) 21.2G7.1

26 89G30

(1) HP MS (2) Ion reactions

(1) 1989ELS/SCH (2) 1999ROD/WAL

26.1G1.2 25.8G1.4

109.0G4.8 108.1G5.8

GIB MS

2002KOS/SCH

(1) 11.9 (2) 35.0 (3) 38.4G1.8

49.8 146.4 160.7G7.5

(1) HP MS (2) CID (3) CID

(1) 1989ELS/SCH (2) 1989MAG/DAV(b) (3) 1994DAL/HON

CuC(C6H6)x–C6H6 xZ0

1

FeCuC–C6H6 CuC–cyclohepta-1, 3,5-trine FeCuC–cyclohepta-1, 3,5-trine CuC–bicyclo[2.2.1]helpa -2,5-diene

CuC–N2

CuC(NO)x–NO xZ0 1

%53 50 %45.7 52.1G2.3 37.1G2.8

CuC(H2O)x–H2O xZ0

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

986

Comprehensive Handbook of Chemical Bond Energies

Table 21.1.2 (continued) BDEs of CuC–X Bonds

The broken bonds (boldfaceZdissociated fregment)

1

2 3 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (4) (1) (2) (3) (3) (5) (3) (5) (6)

34.9 13.9 39.0 40.7G1.6 13.7G1.8 16.4G0.2 12.8G1.0 16.7G0.2 w10.5

kJ/mol 146 58.2 163.2 170.3G6.7 57.3G7.5 68.6G0.8 53.6G4.2 69.9G0.8 w44

Methods (reference in parentheses)

References

(4) CID

(4) 2000VUK/STO

(5) HP MS

(5) 1982HOL/CAS

(6) Extrapolate

(6) This volume

CuC–furan

56

234

FT–ICR

2004GRI/MAN

CuC–NH2

(1) 48.2G3 (2) 45.9G3

202G13 192G13

(1) Ion reactions (2) Review

(1) 1991CLE/ARM (2) 1996ARM/KIC

(1) (1) (1) (2) (1) (2) (2)

237G15 248G10 46G6 58.6G0.8 45G6 53.6G0.8 53.6G0.4

(1) CID

(1) 1998WAL/ARM

(2) HP MS

(2) 1982HOL/CAS

CuC(NH3)x–NH3 xZ0 1 2 3 4

56.6G3.3 59.3G2.4 11.0G1.4 14.0G0.2 10.8G1.4 12.8G0.2 12.8G0.1

CuC(MeCN)x–MeCN xZ0 1 2 3

56.9G0.8 57.0G2.1 20.1G0.5 16.0G0.5

238.2G3.2 238.3G8.6 84.1G2.2 67.0G2.0

CID

2001VIT/VAL

CuC(MeOH)x–MeOH xZ0 1

13.4 13.9

56.1 58.2

HP MS

1989ELS/SCH

CuC–2L LZH2O MeOH EtOH EtOEt MeC(O)OMe

76.0 83.8 88.2 95.6 96.3

318 351 369 400 403

ES MS

1998DEN/KEB

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

MeC(O)Me EtC(O)Et

987

95.2 97.8

398 409

CuC–2L LZEtCl EtBr i-PrBr

72.1 76.5 80.8

302 320 338

ES MS

1998DEN/KEB

CuC(L)x–L, LZDMEZ dimethyl ether, MeOMe x Z0 1 2 3

44.3G2.8 46.1G1.8 13.1G0.9 10.8G2.3

185.2G11.6 193.0G7.7 55.0G3.9 45.3G9.6

CID

2001KOI/ZHA

63.2G1.8 43.1G1.4

264.4G7.7 180.4G5.8

CID

2001KOI/ARM

(1) (2) (1) (2) (2) (2)

62.3 201.8G4.3 64.9 210.0G6.5 65.6G2.4 61.6G5.4

(1) HP MS (2) CID

(1) 1989ELS/SCH (2) 2002CHU/YAN

CuC(L)x-L, LZDXE Zdimethoxyethane xZ 0 1

CuC(Me2CO)x–Me2CO xZ 0 1 2 3

14.9 48.2G1.0 15.5 50.2G1.6 15.7G0.6 14.7G1.3

CuC–S

(1) 62.0G1.8 (2) 48.6G3.5

259.4G8 203.3G14.5

GIB MS

(1) 1995KIC/ARM (2) 2002RUE/ARM

CuC–CS

57.0G2.8

238.3G11.6

GIB MS

2002RUE/ARM

CuC–2L LZMeSH MeSMe MeS(O)Me

92.0 101.4 112.8

385 424 472

ES MS

1998DEN/KEB

CuC–2L LZNH3 Pr–NH2 MeCN MeC(O)NH(Me)

105.4 115.8 108.6 111.0

441 485 454 464

ES MS

1998DEN/KEB

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

988

Comprehensive Handbook of Chemical Bond Energies

Table 21.1.2 (continued) BDEs of CuC–X Bonds

The broken bonds (boldfaceZdissociated fregment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

116.0 135.4

485 567

CuC–pyridine –pyrimidine

59.2G2.4 60.1G2.3

247.5G10.1 251.3G9.8

CID

2000ROD/STA 2001AMU/ROD

CuC(pyrrole)x–pyrrole xZ 0 1

59 44.0

247 184.1

Kinetics

2000GAP/YAN

CuC–adenine

71.2G2.6

298.1G11.0

GIB MS

2002ROD/ARM

CuCLx–L, LZimidazole xZ 0 1 2 3

68.7G1.8 61.8G2.2 19.6G0.6 15.8G0.5

287.5G7.4 258.4G9.2 82.0G2.6 66.0G2.0

CID

2005RAN/AMU

CuC–a-amino acids –arginine (Arg) –lysine (Lys) –valine (Val)

87.0G1.2 84.8G1.2 67.6G1.2

364G5 355G5 283G5

Kinetics

1999CER/WES(b)

CuC–Si –SiH –SiH2 –SiH3

62.1G1.8 58.8G6.5 R55.1G1.6 23.1G6

260G8 246G27 R231G7 97G25

GIB MS

1995KIC/ARM

CuC–Ge

55.1G5.5

231G23

Derived from IP in ref.

1996NIST

Cu2C–H2O –H3N

76.1G13.8 131.4G13.8

318G58 550G58

CS MS

2001SCH/SCH

MeC(O)N(Me)2 1-methyllimidazole

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

989

21.1.3 CuK–X bonds Table 21.1.3 BDEs of CuL–X Bonds

The broken bonds (boldfaceZdissociated fragment) CuK(Cu)x–Cu xZ0

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 37.1

155.2

(1) Derived

(1) 1987LEO/GO

(2) 38.2G2.1

160.0G8.7

(2) PES

(2) 1990HO/ERV

(3) 37.8G3.5 (3) 55.8G3.5

158.2G14.5 233.5G14.5

(3) CID

(3) 2000SPA/LEE

1 2

(3) 44.5G2.8

186.2G11.6

3

(3) 54.2G2.8

226.7G11.6

4

(3) 58.8G6.9

246.0G28.9

5

(3) 66.2G5.1

276.9G21.2

6

(3) 55.6G6.9

232.5G28.9

N

(4) w71.8

w300

(4) Extrapolate

(4) This volume

CuK–Ni

38.1G2.4

159G10

Derived from EA in ref.

1996NIST

CuK–O

74.4G2.4

311.3G10

Derived from EA in ref.

1996NIST

(1) 8.8G0.5

36.7G1.9

(1) PES

(1) 1996MIS/TSU

(2) 9.0 (3) 9.7

37.6 40.5

(2) Derived (3) Derived

(2) 2004TAY/MUN (3) 2005RAT/SAN

(1) 11.5G0.5 (4) w10.5

48.2G1.9 w44

(4) Extrapolate

(4) This volume

CuK(H2O)x–H2O xZ0

1 N

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

990

Comprehensive Handbook of Chemical Bond Energies

21.2 Ag–, AgC–, and AgK–X bonds 21.2.1 Ag–X bonds Table 21.2.1 BDEs of Ag–X Bonds

The Broken Bonds (boldfaceZdissociated fragment) Ag(Ag)x–Ag xZ0

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol 39.0G2 38.5G0.9 37.8G0.8 39.4 38.9G0.7 22.4G3.7

kJ/mol (1) (2) (3) (4) (5)

Ag–Ag on a (100) terrace 6.9

28.9

Review

2004THI/EVA

Ag(100, surf.)–Ag

0.7G0.1 (phys)

2.9G0.5

STM

1998ZHA/BAR

Ag(100, surf.)–Ag

(1) (2) (3) (4)

38.6G4.8 31.8G0.5 36.7 38.6G3.9

(1) (2) (3) (4)

(1) (2) (3) (4)

Ag(110, surf.)–Ag

8.8G0.7

36.7G2.9

HAS

2003PED/BRA

Ag(111, surf.)–Ag

(1) (2) (3) (4) (5)

w14.5 11.6G1.4 17.4 12.5G3.9 14.5G2.9

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Ag(111, surf.)–Ag

(1) 68 (2) 16.4G0.7

285 68.5G2.9

(1) Review (2) STM

(1) 1995SEE/ALL (2) 1998MOR/ROS

AgBr(111, surf.)–Ag

7.8

32.8

Radio

1971TAN/PER

9.2G1.2 7.6G0.1 8.8 9.2G0.9

w3.5 (phys) 2.8G0.3 4.2 3.0G0.9 3.5G0.7

Review Spectroscopy MS Review Spectrometry

References

163G8 161.1G3.9 158.0G3.4 164.8 162.8G2.9 93.6G15.4

1

(1) (2) (3) (4) (5) (1)

Methods (reference in parentheses)

LEIS/TOF STM STM STM

STM STM LEED STM STM

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

(1) (2) (3) (4) (5)

1970DAR 1986MOR 1993RAN/SCH 1996SMI/YAT 1998LAN/MOR

1996LAN/BOE 1997ZHA/BAR 1998ZHA/BAR 1998BAR/STO

1995MEY/VRI 1995BRO/BRU 1996LUO/WOL 1998MOR/ROS 1998ROO/TRI

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

991

Pt(111, surf.)Ag–Ag

1.4G0.2

5.8G1.0

STM

1995BRU/BRO

Ag–Cu

(1) 41.6 (2) 41G2 (3) 41.0G2.3

174.1 172G8 171.5G9.6

(1) MS (2) Review (3) Spectroscopy

(1) 1960ACK/STA (2) 1979DAR (3) 1991BIS/MAR

Ag–Au

(1) 48.5 (2) 48.5G2.3

202.9 202.9G9.6

(1) MS (2) Review

(1) 1960ACK/STA (2) 1986MOR

Ag–Li

(1) 41.5G1.5 (2) 47.5 (3) 44.5

173.6G6.3 198.8 186.1

(1) MS (2) PI (3) R2PI

(1) 1974NEU/ZMB(b) (2) 1995PIL/DUN (3) 1997BRO/KNI

Ag–Na

31.8G3

133.1G12.6

Recommended

1979PEL/PIA

Ag–Nd

!51

!213

MS

1974GUR/KAR

Ag–Eu

30.4G3.1

127G13

MS

1989CHA/GIN

Ag–Dy

(1) 30.6G5.7 (2) 31G4.5

128G24 130G19

MS

(1) 1989CHA/GIN (2) 1981HIL

Ag–Ho

29.6G4.5

124G19

MS

1989CHA/GIN

Ag–Mn

23.7G5

99.2G21

Review

1986MOR

Ag(polycs. surf.)–Ni

26 (phys)

109

LEED

1970PIN/GRE

Ag(polycs. surf.)–Ni

98

410

Review

1995SEE/ALL

Ag–Al

43.9G2.2

183.7G9.2

MS

1973CUT/FAB

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

992

Comprehensive Handbook of Chemical Bond Energies

Table 21.2.1 (continued) BDEs of Ag–X Bonds

The Broken Bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Ag–Ga

(1) 43.0G3.6 (2) 38G4

180G15 159G17

(1) MS (2) Review

(1) 1972CAR/BER (2) 1974GUR/KAR

Ag–In

(1) 42G4 (2) 39.8G1.2

176G17 166.5G4.9

(1) Review (2) MS

(1) 1974GUR/KAR (2) 1989BAL/NUN

Ag(100, surf.)–In

7.1G0.7 (phys)

30.0G3

PACT

1990FIN/WES

Ag(100, surf.)–In

70

293

Review

1995SEE/ALL

Ag(110, surf.)–He

(1) 0.14 (2) 0.14

0.58 0.58

Scattering

(1) 1982LUN/MAT (2) 1987JON/WEA

Ag(111, surf.)–He

(1) (2) (3) (4)

1.1 0.68 0.9 0.68

Scattering

(1) (2) (3) (4)

Ag(111, surf.)–Ar

2.3

9.6

LEED

1982UNG/BRU

Ag(110, surf.)–Kr

1.4

5.9

LEED

1969STE/MOR

Ag(111, surf.)–Kr

2.5

10.3

LEED

1982UNG/BRU

Ag(110, surf.)–Xe

6.1

25.6

LEED

1969STE/MOR

Ag(111, surf.)–Xe

(1) (2) (3) (4)

18G1 20.4G1.4 21.8 20.4G1.4

(1) (2) (3) (4)

(1) (2) (3) (4)

0.3 0.16 0.2 0.16

4.3 4.9G0.3 5.2 4.9G0.3

LEED LEED TDS Review

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

1972WEI 1973SAU/MER 1980HOR/YER 1987JON/WEA

1976MCE/RAP 1982UNG/BRU 1986BEH/BRU 1991VID/IHM

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

993

Ag–H

(1) 55G3 (2) 50.5G2 (3) 48.4G2.3

230G13 211.3G8.4 202.4G9.6

(1) Review (2) MS (3) Ion reactions

(1) 1970DAR (2) 1979KAN/MOO (3) 1995CHE/ARM

Ag–D

54.2

226.8

Review

1979HUB/HER

Ag(polycs. surf.)–H

40

167

Electrochemical

1970KRI

Ag(111, surf.)–H

(1) 57.6 (2) 52

241 218

Review

(1) 1988CHR (2) 1991BEN

Ag–F

(1) (2) (3) (4)

84.7G3.9 84.8 85.3G1.4 82.3

354.4G16.3 354.8 356.9G5.8 344.3

(1) (2) (3) (4)

Review Review MS MS

(1) (2) (3) (4)

1968GAY 1979HUB/HER 1991HIL/LAU 2005HIL

Ag–Cl

(1) (2) (3) (4)

75G5 75.1 75.1 75.1

314G21 314.2 314.2 314.2

(1) (2) (3) (4)

Review Review MS Derived

(1) (2) (3) (4)

1970DAR 1979HUB/HER 1996HIL/LAU(b) 2004HIL/LAU

Ag(111, surf.)–Cl

w60

w251

Est. by exp.

2003PUR/BOC

Ag–Br

(1) (2) (3) (4)

70G7 70G10 72.4 67.0G0.3

293G29 293G42 302.9 280.3G1.3

(1) (2) (3) (4)

Review Review Review Derived

(1) (2) (3) (4)

1968GAY 1970DAR 1979HUB/HER 2005HIL/LAU(b)

Ag–I

(1) (2) (3) (4)

56G7 68.7 60.9 60.2

234G29 287.4 254.9 251.9

(1) (2) (3) (4)

Review Review Review Derived

(1) (2) (3) (4)

1968GAY 1970DAR 1979HUB/HER 2005HIL

Ag–O

(1) 53.5G3.5 (2) 52.7G5

223.8G14.6 221G21

(1) MS (2) Review

(1) 1972SMO/MAN (2) 1990SIM/BEA

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

994

Comprehensive Handbook of Chemical Bond Energies

Table 21.2.1 (continued) BDEs of Ag–X Bonds

The Broken Bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ag(surf.)–O

80

335

TPD

1994MAD/ROB

Ag(100, surf.)–O

84.0

351.5

Review

2003ZEI

Ag(110, surf.)–O

86.4

361.5

Review

2003ZEI

Ag(111, surf.)–O

80

335

TDS

1985CAM

Ag–S

51.8G3.5

216.7G14.6

MS

1972SMO/MAN

Ag(100, surf.)–S Ag(110, surf.)–S Ag(111, surf.)–S

81 84 78

339 351 326

Review

1982BAR/AGR

Ag–Se –Te

50.2G3.5 46.8G3.5

210.0G14.6 195.8G14.6

MS

1972SMO/MAN

Ag(100, surf.)–N Ag(110, surf.)–N Ag(111, surf.)–N

105.0 108.0 100.0

439.3 451.9 418.4

Review

2003ZEI

Ag–Bi

46G10

192G42

Review

1974GUR/KAR

Ag(111, surf.)–C

w70

w293

Est. by exp.

2003PUR/BOC

Ag–Si

44.2G2.3

185.1G9.6

TOF MS

1995SCH/PAU

Ag–Ge

41.7G5

174.5G21

MS

1972NEC/SOD

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

995

Ag–Sn

32.5G5

136G21

MS

1962ACK/DRO

Ag(110, surf.)–KCl

36.9

154

Photoemission

1990SEN

Ag(111, surf.)–KCl

25.4G2.3

106G10

AES

1986SEN

Ag(110, surf.)–H2

0.73

3.06

Scattering

1985YU/WHA

Ag(111, surf.)–H2

0.75

3.14

Scattering

1985YU/WHA

Ag(110, surf.)–D2

0.73

3.06

Scattering

1985CHI/MAT

Ag(111, surf.)–D2

w0.74

w3.1

Scattering

1985YU/WHA

Ag(111, surf.)–HD

1.2 (phys)

5.1

Scattering

1984WHA/LIG

Ag(100, surf.)–Cl2 Ag(110, surf.)–Cl2 Ag(111, surf.)–Cl2

60 55 55

251 230 230

Calorimetry

1979TU/BLA

Ag(surf.)–O2

14.8

62

Review

1982RAO/KAM

Ag(plate, surf.)–O2

8.3

34.7

Calorimetry

1979TOY/SOM

Ag(100, surf.)–O2

11.5G2.8

48.2G11.6

Desorption

1997MON/VAL

Ag(110, surf.)–O2

1.8 (phys)

7.5

LEED

1969STE/MOR

Ag(110, surf.)–O2

(1) 11 (2) 10.8 (3) 5.1G1.2

46 45.2 21.2G4.8

(1) TDS (2) TDS (3) STM

(1) 1980BAR/MAD (2) 1985CAM (3) 1997BAR/ZAM

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

996

Comprehensive Handbook of Chemical Bond Energies

Table 21.2.1 (continued) BDEs of Ag–X Bonds

The Broken Bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ag(110, surf.)–O2

(1) 40G2 (2) 35.1

167G8 147

(1) TDS (2) Re-anal.

(1) 1976ENG/MEN (2) 1980BOW

Ag(111, surf.)–O2

(1) 14.7 (2) 11–21 (3) 12.4

61.5 46–88 51.9

TD

(1) 1966OTT (2) 1974ROV/PRA (3) 1985CAM

Ag(111, surf.)–O2

35

146

TDS

1974ROV/PRA

Ag(110, surf.)–OH

55

230

TDS

1987BAN/MAD

Ag(polycr. surf.)–CO

(1) 8.7 (2) 18–20

36 75–84

(1) Isothermal (2) IR

(1) 1953TRA (2) 1967KAV/SOK

Ag(110, surf.)–CO

13.9G0.7

58G3

LEED

1976MCE/PRI

Ag(111, surf.)–CO

6.5G0.4

27G1.5

TDS

1976MCE/PAP

Ag(100, surf.)–N2

0.9

3.8

Scattering

1982MUH/SER

Ag(110, surf.)–N2

2.4

10

TDS

1998RAM/GIR

Ag(110, surf.)–NO

w25

w104

TDS

1976MCE/PAP

Ag(111, surf.)–NO

4–5 (phys)

17–21

TDS

1984BEH/BRU

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

Ag(110, surf.)–H2O

(1) (2) (3) (4)

Ag(110, surf.)–D2O

Ag(110, surf.)–SO2

Ag(Ag)x–NH3 xZ0

1

11.6G0.3 9–10 14.3G0.4 11.5G0.5

997

48.5G1.3 38–42 60.0G1.7 48.3G2.2

(1) (2) (3) (4)

15.2G0.4

63.4G1.7

TPD

1989WU/PET

9.8–15.3

41–64

TPRS

1984OUT/MAD

(1) (2) (3) (1) (4)

!40 8G13 8G13 62.8G4.2 61.5G8.4

(1) PD (2) Derived (3) Derived

(1) 1996MIT/LIA (2) 2003MIY/SUG (3) 2005LI/SOH

(4) IRMPD

(4) 1995RAY/LIA

!9.5 2G3.1 2G3 15G1 14.7G2

TPD TDS TPD SHG

(1) (2) (3) (4)

1984KLA/MAD 1987BAN/MAD 1989WU/PET 2005DOU/JEN

Ag(Ag)x–NH3 xZ9 15

9.2 15.3G1

38.5 64.0G4.2

Equilibrium

1996LIA/MIT

Ag(100, surf.)–NH3

11

46

Spectrometry

1989THO/MAD

Ag–CH3

32.1G1.6

134.1G6.8

Ion reactions

1995CHE/ARM

Ag(110, surf.)–CH4

1.0 (phys)

4.2

LEED

1969STE/MOR

Ag(111, surf.)–CH3X XZCl Br I

6.7 7.6 9.3

28.2 31.8 39.0

TPD

1989ZHO/SOL

14.7

61.5

TPRS

1978WAC/MAD(b)

Ag(110, surf.) –CH3OH

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

998

Comprehensive Handbook of Chemical Bond Energies

Table 21.2.1 (continued) BDEs of Ag–X Bonds

The Broken Bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ag(111, surf.) –CH2CHCl –CHCH2

(1) w10.7 (2) w43

w44.8 w178

(1) TDS (2) Est. by exp.

2003PUR/BOC

Ag(110, surf.)–C2H2

1.0 (phys)

4.2

LEED

1969STE/MOR

Ag(110, surf.)–C2H4

1.6 (phys)

6.7

LEED

1969STE/MOR

Ag(100, surf.)–C2H4

6.2

26

Mol. beam

2002VAT/ROC

Ag(111, surf.)–C2H4

(1) w9 (2) w9.3

w38 w39

(1) TPD (2) RAIR

(1) 1992ZHO/WHI (2) 2001STA/WU

Ag(111, surf.) –C2H4O

10.8

45

RAIR

2001STA/WU

Ag(110, surf.)–C3H6 –C3H8

11.7G0.4 9.2G0.4

49.0G1.7 38.5G1.7

TPD

1996CRE/MAD

Ag(110, surf.)–C4H8

13.3G0.7

55.6G2.9

TPD

1995CRE/MAD(b)

Ag(110, surf.)–iso-C4H8

13.3G0.8

55.6G3.3

TPD

1995CRE/MAD(b)

Ag(111, surf.) –PhOH

15.5

64.9

TPD

2001LEE/RYU

Ag(111, surf.) –pyridine

11.5

48.3

TPD

2001YAN/ROC

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

999

Ag(111, surf.) –aniline

(1) 12.5 (2) 17.7G1.2

52.5 74G5

TPD

(1) 2001YAN/ROC (2) ROC/YAN

Ag(111, surf.) –tetracene

29–31

120–130

TPD

2005LAN/HAU

Ag(111, surf.) –CH3(CH)2SH

33.0

138

TOF/DRS

2006ROD/GAY

Ag2–Ar –Kr –Xe

(1) 0.79 (1) 1.13 (2) 3.53

3.3 4.73 14.8

Spectra.

(1) 1991WIL/CHE(b) (2) 1992ROB/WIL

21.2.2 AgC–X bonds Table 21.2.2 BDEs of AgD–X Bonds

The broken bonds (boldfaceZdissociated fragment) AgC–Ag

AgC(Ag)x–Ag xZ2 4 6 7 8 10 12 13 14 15 16

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 39.9 (2) 40.1G2.1

166.8 167.9G8.7

(1) Derived (2) CID

(1) 1996SMI/YAT (2) 1999KRU/DIE(b)

(1) (1) (1) (1) (1) (1) (1) (2) (1) (2) (1) (2) (1) (1) (2)

101.3G4.8 123.5G15.4 211.3G15.4 284.6G19.3 152.3G10.6 180.4G10.6 193.0G10.6 176G6 242.2G13.5 238G16 197.8G10.6 186G12 246.0G13.5 226.7G12.5 223G26

(1) CID

(1) 1999KRU/DIE(b)

(2) Re-analyzed

(2) 2003HAN/HER

24.2G1.2 29.5G3.7 50.5G3.7 68.0G4.6 36.4G2.5 43.1G2.5 46.1G2.5 42.0G1.4 57.9G3.2 56.9G3.9 47.3G2.5 44.5G2.8 58.8G3.2 54.2G3.0 53.3G6.2

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

1000

Comprehensive Handbook of Chemical Bond Energies

Table 21.2.2 (continued) BDEs of AgC–X Bonds

The broken bonds (boldfaceZdissociated fragment) 17 18 19 20 21 22 23 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (1) (1) (1) (1) (1) (1) (3)

60.2G3.2 53.7G3.0 59.5G3.2 43.4G2.5 50.5G2.8 44.5G2.5 50.3G2.8 w59.8

kJ/mol 251.8G13.5 224.8G12.5 248.9G13.5 181.4G10.6 211.3G11.6 186.2G10.5 210.3G11.6 w250

Methods (reference in parentheses)

References

(3) Extrapolate

(3) This volume

AgC(Ag)x–Ag2 xZ0 2 4 8 10

62.3G3.2 45.4G2.5 52.1G3.9 49.3G3.0 55.6G3.0

260.5G13.5 190.1G10.6 218.1G16.4 206.5G12.5 232.5G12.5

CID

1999KRU/DIE(b)

AgC–Cu

36.2G2.4

151.6G10

1996NIST

–Eu –Ho

20G11.9 37G14.6

85G50 155G61

Derived from IP in ref.

AgC–Fe

46G7

192G29

FT-ICR

1991NG/GOR

AgC–Al

2G12

9G50

Derived from IP in ref.

1996NIST

AgC–H

10.4G1.4

43.5G5.9

GIB MS

1995CHE/ELK

AgC–F

(1) w3 (2) 5.6G6.5

w13 24G27

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

AgC–Cl

(1) 17 (2) 7.6G7.2

71 32G30

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

1001

AgC–Br –I

34.9G7.3 27.7G7.3

146G31 116G31

Derived from IP in ref.

1996NIST

AgC–CH2 –CH3

R25.6G0.9 R15.9G1.2

R107G4 R66.6G4.8

Ion reactions

1995CHE/ARM

AgC 5 ðCH4 Þx –CH4 xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

6.7G0.2 5.9G0.3 5.0G0.5 4.5G0.2 w1.8 w2

28.0G0.8 24.7G1.3 20.9G2.1 18.8G0.8 w7.5 w8

(1) Equilibrium

(1) 2005MAN/KEM(b)

(2) Extrapolate

(2) This volume

(1) (2) (3) (4) (1) (4) (4) (4) (4) (4) (5)

33.7 R5.3G1.6 34 32.2G3.0 32.4 30.1G1.3 13.6G0.8 6.5G0.8 4.4G0.6 w3.3 w3.2

141 R22G7 142 134.7G12.6 136 125.9G5.4 56.9G3.3 27.2G3.3 18.4G2.5 w13.8 w13.5

(1) (2) (3) (4)

(1) (2) (3) (4)

(5) Extrapolate

(5) This volume

AgC 2 ðC2 H4 Þx –C2 H4 xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

24.7G2.0 22.5G1.8 12.5G1.0 7.7G0.6 2.9G0.8 w3.2

103.3G8.4 94.1G7.5 52.3G4.2 32.2G2.5 12.1G3.3 w13.5

(1) Equilibrium

2005MAN/KEM

(2) Extrapolate

(2) This volume

AgC 3 ðC2 H4 Þx –C2 H4 xZ0 1 2 3

21.6G0.5 19.8G0.6 17.3G0.3 5.7G0.4

90.4G2.1 82.8G2.5 72.4G1.3 23.8G1.7

Equilibrium

2005MAN/KEM(b)

AgC 4 ðC2 H4 Þx –C2 H4 xZ0 1 2 3

19.4G1.4 18.7G0.6 17.6G0.2 12.8G0.5

81.2G5.9 78.2G2.5 73.6G0.8 53.6G2.1

Equilibrium

2006MAN/KEM

AgC(C2H4)x–C2H4 xZ0

1 2 3 4 5 N

HP MS GIB MS Review Equilibrium

1991GUO/CAS 1995CHE/ARM 1998SCH/SCH 2005MAN/KEM

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

1002

Comprehensive Handbook of Chemical Bond Energies

Table 21.2.2 (continued) BDEs of AgC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

AgC 5 ðC2 H4 Þx –C2 H4 xZ0 1 2 3 4 5 N

(1) (1) (1) (1) (1) (1) (2)

AgC 6 ðC2 H4 Þx –C2 H4 xZ0 1 2 3 4 5

26.0G2 22.3G0.3 14.8G0.4 11.4G0.3 8.6G0.4 6.9G0.6

AgC 7 ðC2 H4 Þx –C2 H4 xZ0 1 2 3 4 5 6

18.8G0.8 18.4G0.8 25.9G0.5 9.3G0.4 8.9G0.4 4.5G0.4 w3.2

kJ/mol 78.7G3.3 77.0G3.3 108.4G2.1 38.9G1.7 37.2G1.7 18.8G1.7 w13.5

Methods (reference in parentheses)

References

(1) Equilibrium

(1) 2005MAN/KEM(b)

(2) Extrapolate

(2) This volume

108.8G8.4 93.3G1.3 61.9G1.7 47.7G1.3 36.0G1.7 28.9G2.5

Equilibrium

2006MAN/KEM

26.7G0.5 22.5G0.7 12.9G0.3 10.1G0.2 8.2G0.4 6.5G0.5 5.6G0.5

111.7G2.1 94.1G2.9 54.0G1.3 42.3G0.8 34.3G1.7 27.2G2.1 23.4G2.1

Equilibrium

2006MAN/KEM

AgC 8 ðC2 H4 Þx –C2 H4 xZ0 1 2 3 4 5 6 7

17.7G0.7 15.5G0.4 11.3G0.2 10.8G0.6 9.7G0.6 7.2G0.4 6.2G0.6 w5.6

74.1G2.9 64.9G1.7 47.3G0.8 45.2G2.5 40.6G2.5 30.1G1.7 25.9G2.5 w23.4

Equilibrium

2006MAN/KEM

AgC 9 ðC2 H4 Þx -C2 H4 xZ0 1 2 3

16.5G0.6 14.9G0.7 12.7G0.4 10.8G0.2

69.0G2.5 62.3G2.9 53.1G1.7 45.2G0.8

Equilibrium

2006MAN/KEM

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

4 5 6

1003

9.6G0.4 8.1G0.4 6.7G0.4

40.2G1.7 33.9G1.7 28.0G1.7

AgC 10 ðC2 H4 Þx –C2 H4 xZ0 1

14.8G0.7 15.9G0.5

61.9G2.9 66.5G2.1

Equilibrium

2006MAN/KEM

AgC 11 ðC2 H4 Þx –C2 H4 xZ0 1

14.8G0.5 13.8G0.5

61.9G2.1 57.7G2.1

Equilibrium

2006MAN/KEM

AgC 12 ðC2 H4 Þx –C2 H4 xZ0 1

16.7G0.6 13.6G0.7

69.9G2.5 56.9G2.9

Equilibrium

2006MAN/KEM

AgC 13 –C2 H4

16.3G0.4

68.2G1.7

Equilibrium

2006MAN/KEM

AgC–C2H5

15.7G1.8

65.7G7.5

Ion reactions

1995CHE/ARM

AgC(C3H6)x–C3H6 xZ0 1 2 3 3 4 N

(1) (1) (1) (1) (1) (1) (2)

39.2G3.0 32.9G1.5 13.3G1.0 7.0G1.0 7.0G1.0 3.0G0.8 w4

164.0G12.6 137.7G6.3 55.6G4.2 29.3G4.2 29.3G4.2 12.6G3.3 w17

(1) Equilibrium

(1) 2005MAN/KEM

(2) Extrapolate

(2) This volume

AgC 2 ðC3 H6 Þx –C3 H6 xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

28.1G1.5 25.8G1.5 12.4G0.8 9.3G0.5 4.4G0.6 w4

117.6G6.3 107.9G6.3 51.9G3.3 38.9G2.1 18.4G2.5 w17

(1) Equilibrium

(1) 2005MAN/KEM

(2) Extrapolate

(2) This volume

AgC 3 ðC3 H6 Þx –C3 H6 xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

26.2G0.6 21.4G0.9 18.9G0.4 4.9G0.2 4.3G0.6 w4

109.6G2.5 89.5G3.8 79.1G1.7 20.5G0.8 18.0G2.5 w17

(1) Equilibrium

(1) 2006MAN/KEM

(2) Extrapolate

(2) This volume

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

1004

Comprehensive Handbook of Chemical Bond Energies

Table 21.2.2 (continued) BDEs of AgC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

AgC 4 ðC3 H6 Þx –C3 H6 xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

AgC 5 ðC3 H6 Þx –C3 H6 xZ0 1 2 3 4 5

21.7G0.4 20.5G0.7 25.3G0.4 11.3G0.6 9.4G0.7 6.0G0.7

AgC 6 ðC3 H6 Þx –C3 H6 xZ0 1 2 3 4 5

22.8G1.1 21.0G0.5 18.4G0.7 12.5G0.6 3.8G0.6 w4

kJ/mol 95.4G4.6 87.9G2.1 77.0G2.9 52.3G2.5 15.9G2.5 w17

Methods (reference in parentheses)

References

(1) Equilibrium

(1) 2006MAN/KEM

(2) Extrapolate

(2) This volume

90.8G1.7 85.8G2.9 105.9G1.7 47.3G2.5 39.3G2.9 25.1G2.9

Equilibrium

2006MAN/KEM

25.9G0.9 20.0G0.7 15.0G1.0 13.9G1.1 11.1G0.6 9.8G0.5

108.4G3.8 83.7G2.9 62.8G4.2 58.2G4.6 46.4G2.5 41.9G2.1

Equilibrium

2006MAN/KEM

AgC 7 ðC3 H6 Þx –C3 H6 xZ0 1 2 3 4 5 6

25.2G1.0 21.0G0.9 14.4G0.5 13.2G0.8 12.0G0.3 10.8G0.3 8.5G0.2

105.4G4.2 87.9G3.8 60.2G2.1 55.2G3.3 50.2G1.3 45.2G1.3 35.6G0.8

Equilibrium

2006MAN/KEM

AgC 8 ðC3 H6 Þx –C3 H6 xZ0 1 2 3 4 5 6

19.7G0.8 16.9G0.5 15.2G0.3 12.9G0.6 11.6G0.3 10.6G0.5 w8.3

82.4G3.3 70.7G2.1 63.6G1.3 54.0G2.5 48.5G1.3 44.4G2.1 w34.7

Equilibrium

2006MAN/KEM

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

1005

AgC 9 ðC3 H6 Þx –C3 H6 xZ0 1 2 3 4 5 6 7

19.3G0.6 16.2G0.5 14.6G0.8 13.0G0.8 11.2G0.4 10.2G0.2 8.5G0.2 w7

80.8G2.5 67.8G2.1 61.1G3.3 54.4G3.3 46.9G1.7 42.7G0.8 35.6G0.8 w29

Equilibrium

2006MAN/KEM

AgC(L)x–L, LZisoprene xZ0 1

39.2G4.6 38.5G4.6

164G19 161G19

Kinetics

1997HO/YAN

O40.1

O167.6

FT-MS

1988BUC/GOR(b)

37.8G4.6 39.0G4.6

158G19 163G19

Kinetics

1997HO/YAN

(1) 37.4G1.7 (2) 39.9G4.6 (2) 34.6G4.6

156.5G7.1 167G19 145G19

(1) Ion reactions (2) Kinetics

(1) 1993CHE/ARM (2) 1997HO/YAN

AgC 2 –C6 H6

%42

%176

PD

1992WIL/TEH

AgC–C6H5CH3

%45

%188

PD

1991WIL/CHE

AgC–2(C6H6)

68.2G3

285G13

HP MS

1998DEN/KEB

AgC–COT, COTZ cyclooctatetraene

w60%

w251%

Derived

2004JAE/DUN

AgC x ðMÞ2 –L; LZ butadiene; MZ sKC4 H9 NH2 ; xZ 3; 5

AgC(L)x–L, LZ2-pentene xZ0 1

AgC(C6H6)x–C6H6 xZ0 1

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

1006

Comprehensive Handbook of Chemical Bond Energies

Table 21.2.2 (continued) BDEs of AgC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

AgC–O

29.4G1.2

123G5

Ion beam

1995CHE/ARM(c)

AgC(O2)x–O2 xZ0 1 2 3

7.1G0.2 7.6G0.2 5.7G0.2 w4.8

29.7G0.8 31.8G0.8 23.6G0.8 w20

Equilibrium

2003MAN/KEM

AgC(CO)x–CO xZ0 1 2 3

21.3G1.2 26.1G1.0 13.1G1.9 10.8G1.0

89G5 109G4 55G8 45G4

CID

1995MEY/CHE

(1) (2) (1) (2) (1) (2) (1) (2) (1) (1) (3)

139.3G0.8 134G8 106.3G1.3 127G8 62.8G0.4 63G9 62.3G0.8 51G12 57.3G0.8 55.6G2.5 w44

(1) HP MS (2) GIB MS

(1) 1982HOL/CAS (2) 2003KOI/LAR(b)

(3) Extrapolate

(3) This volume

AgC(H2O)x–H2O xZ0 1 2 3 4 5 N

33.3G0.2 32.0G2 25.4G0.3 30.4G2 15.0G0.1 15.1G2.2 14.9G0.2 12.2G2.9 13.7G0.2 13.3G0.6 w10.5

AgC(MeOH)x–MeOH xZ0 1 2 3

36.6G1.7 32.7G1.4 15.3G1 13.1G2.4

153G7 137G6 64G4 55G10

CID

2003KOI/LAR

AgC–CH3COH

43.6G4.6

182G19

Kinetics

1997HO/YAN

AgC(L)x–L, LZCH3OCH3 xZ0

35.1G2

147G8

CID

2003KOI/LAR(b)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

1 2 3

AgC(L)x–L, LZCH3COCH3 xZ0 1

33.9G2 15.1G4.1 8.1G2.4

142G8 63G17 34G10

(1) %31 (2) 38.3G4.6 (2) 40.8G4.6

%130 160G19 171G19

(1) PD (2) Kinetics

1007

(1) 1991WIL/CHE (2) 1997HO/YAN

AgC(L)x–L, LZCH3CN xZ0 39.4 1 34.7

164.8 145.2

CID

2001SHO/ARI

AgC(L)2–L, LZC5H5N xZ2 3

16.7G0.2 17.9G0.2

69.9G0.8 74.9G0.8

HP MS

1982HOL/CAS

AgC–2L LZH2O MeOH EtOH

56.5G3 64.6G3 70.9G3

236G13 270G13 297G13

HP MS

1998DEN/KEB

AgC–2L LZEtBr i-PrBr

63.6G3 67.1G3

266G13 281G13

HP MS

1998DEN/KEB

AgC–2L LZMeC(O)OMe MeC(O)Me EtOEt

73.3G3 71.4G3 78.5G3

307G13 299G13 328G13

HP MS

1998DEN/KEB

AgC–S

29.4G3.1

123G13

Ion reactions

2003ARM

AgC–CS

36.3G4.8

152G20

GIB MS

2000ROD/ARM(b)

AgC(NH3)x–NH3 xZ0 1

(1) 40.6G3 (2) 36.9G0.8

170G13 154.4G3

(1) CID (2) HP MS

(1) 2002ARI/ROD (2) 1982HOL/CAS

(continued)

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

1008

Comprehensive Handbook of Chemical Bond Energies

Table 21.2.2 (continued) BDEs of AgC–X Bonds

The broken bonds (boldfaceZdissociated fragment) 2 3 4

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 14.6G0.1 (2) 13.0G0.1 (2) 12.8G0.2

61.1G0.4 54.4G0.4 53.6G0.8

AgC–2L LZNH3 MeCN MeSMe

85.6G3 84.5G3 86.4G3

358G13 354G13 361G13

HP MS

1998DEN/KEB

AgC 2 ðAgÞx –Ag xZ8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24

32.7G3 48.9G4.2 35.7G3.5 33.4G2.8 39.4G2.8 45.4G3 51.0G3.2 61.8G3.5 51.4G3 63.3G3.7 54.7G3 61.8G3.5 51.2G2.8 64.6G3.7 45.4G2.5 51.9G3 49.3G2.8

137.0G12.5 204.5G17.4 149.5G14.5 139.9G11.6 165.0G11.6 190.1G12.5 213.2G13.5 258.6G14.5 215.2G12.5 264.6G15.4 228.7G12.5 258.6G14.5 214.2G11.6 270.2G15.4 190.1G10.6 217.1G12.5 206.5G11.6

CID

1999KRU/DIE

AgC 2 ðO2 Þx –O2 xZ0 1 2

4.9G0.4 4.5G0.3 w3.5

20.5G1.7 18.8G1.3 w14.6

Equilibrium

2003MAN/KEM

7366—CHAPTER 21—5/2/2007—08:22—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

1009

21.2.3 AgK–X bonds Table 21.2.3 BDEs of AgL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(1) 45.2G3.5 (2) 32.5 (3) 42.3

189.0G14.5 135.9 177

(1) PES (2) Derived (3) Review

(1) 1993HO/POL (2) 1996SMI/YAT (3) 2001ARM

AgK(Ag)x–Ag xZ1 2 3 4 5 6 7 8 9 N

(1) (1) (1) (1) (2) (2) (2) (2) (2) (3)

233 131 187 182 239.3G7.7 159.2G3.9 219.0G7.7 175.6G3.9 229.6G7.7 w250

(1) Review

(1) 2001ARM

(2) PD

(2) 1999SHI/SPA

(3) Extrapolate

(3) This volume

AgK(Ag2)x–Ag2 xZ2 3 4

59.0G1.6 52.2G2.1 56.5G2.5

PD

1999SHI/SPA

AgK–Ag

55.7 31.3 44.7 43.5 57.2G1.8 38.0G0.9 52.3G1.8 42.0G0.9 54.9G1.8 w59.8

247.0G6.8 218.4G8.7 236.4G10.6

References

21.3 Au–, AuC–, and AuK–X bonds 21.3.1 Au–X bonds Table 21.3.1 BDEs of Au–X Bonds

The broken bonds (boldfaceZdissociated fragment) Au(Au)x–Au xZ0

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 53.9 (2) 53.7G0.5

225.6 224.7G1.9

Methods (reference in parentheses) (1) MS (2) PES

References (1) 1957SCH (2) 1990HO/ERV

(continued)

7366—CHAPTER 21—5/2/2007—08:23—CRCPAG—15377—XML MODEL B – pp. 967–1026

1010

Comprehensive Handbook of Chemical Bond Energies

Table 21.3.1 (continued) BDEs of Au–X Bonds

The broken bonds (boldfaceZdissociated fragment)

1

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (3) (4) (5) (6)

53.7G0.2 54.1G0.1 54.2 34.8G3.5

Methods (reference in parentheses)

kJ/mol 224.7G0.8 226.2G0.5 226.6 145.7G14.5

(3) (4) (5) (6)

Spectrometry Spectrometry Review Derived

References (3) (4) (5) (6)

1991BIS/MOR 1994JAM/KOW(b) 1996SMI/YAT 1986MOR

TbAux–Au xZ1 2

86.7G1 84.5G1

362.9G4 353.5G4

Derived from DfH0 in ref.

2004MES/KLE

DyAux–Au xZ1 2

86.7G1 84.8G1

362.6G4 354.7G4

Derived from DfH0 in ref.

2004MES/KLE

ErAux–Au xZ1 2

87.0G1 83.3G1

363.9G4 348.4G4

Derived from DfH0 in ref.

2004MES/KLE

TmAux–Au xZ1 2

87.7G1 83.5G1

367.0G4 349.3G4

Derived from DfH0 in ref.

2004MES/KLE

Au(100, surf.)–Au

w14

w58

STM

1994GUN/KOP

Au(110, surf.)–Au

(1) 16.1G2.3 (2) 11.2

67.5G9.6 47.0

(1) STM (2) Photoemission

(1) 1995KUI/HOO (2) 2005POP/REI

Au–Cu

(1) 55.4 (2) 54.9G2.3 (3) 54.3G0.3

231.8 229.7G9.6 227.1G1.2

(1) MS (2) Review (3) Spectrometry

(1) 1960ACK/STA (2) 1986MOR (3) 1993BEH/ARR(b)

Au–Ag

(1) 48.5 (2) 48.5G2.3

202.9 202.9G9.6

(1) MS (2) Review

(1) 1960ACK/STA (2) 1986MOR

7366—CHAPTER 21—5/2/2007—08:23—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

1011

Au(111, surf.)–Ag

1.5

6.2

Photoemission

2005POP/REI

Au–Li –Na

(1) 68.0G1.6 (2) 51.4G3

284.5G6.7 215.1G12.6

MS

(1) 1974NEU/ZMB (2) 1977PIA/GIN

Au–Rb –Cs

58.1G0.7 60.4G0.8

243G3.3 253G3.5

MS

1981BUS/WEI

Au–Be

(1) 68G2 (2) 73 (3) 56.8G1.0

285G8 305 237.7G4.0

(1) Review (2) Review (3) MS

(1) 1968GAY (2) 1973LIT/SPA (3) 2004BAL/CIO

Au–Mg

42.8G0.6

179.1G2.7

MS

2003BAL/CIC

Au–Ca

(1) 57.8 (2) 59.8G1.0

242 250.4G4

(1) Review (2) MS

(1) 1980GIN (2) 2004BAL/CIO

Au–Sr

(1) 88 (2) 63G10

368 264G42

Review

(1) 1973LIT/SPA (2) 1974GUR/KAR

Au–Ba

60.9G2.4

254.8G10

Review

1980GIN

Au–Sc –Y –La

(1) (1) (1) (2) (1) (1) (1) (1) (1) (1) (1) (1)

280G40 310G12 457G28 335.7G9.6 322G18 311G25 294G29 245G12 285G33 259G24 267G35 332G19

(1) MS

(1) 1989CHA/GIN

(2) Review

(2) 1986MOR

309G29 318G29

(1) MS (2) Review

(1) 1967GIN/BLU (2) 1974GUR/KAR

–Ce –Pr –Nd –Eu –Tb –Dy –Ho –Lu

Au–U

66.9G9.6 74.1G3 109G7 80.2G2.3 77G4.3 74.3G6 70.3G7 58.6G3 68.1G8 61.9G5.7 63.8G8.4 79.3G4.5

(1) 73.8G7 (2) 76G7

(continued)

7366—CHAPTER 21—5/2/2007—08:23—CRCPAG—15377—XML MODEL B – pp. 967–1026

1012

Comprehensive Handbook of Chemical Bond Energies

Table 21.3.1 (continued) BDEs of Au–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Au–V

58.8G2.1

246.0G8.7

Review

1986MOR

Au–Cr

(1) 50.5G1.5 (2) 53.5G6.9

211.3G6.5 223.7G28.9

Review

(1) 1970DAR (2) 1986MOR

Au–Mn

(1) 43.4G3.0 (2) 47.3G5

181.6G12.6 197.7G21

(1) MS (2) Review

(1) 1968SMO/DRO (2) 1986MOR

Au–Fe

44.7G4.6

187.0G19.3

Review

1986MOR

Au–Co –Rh

52.1G3.9 55.6G7

218.0G16.4 232.6G30

Review

1986MOR

Au–Ni

(1) 58.8G6.9 (2) 59.0G3.9

246G29 247G16.4

(1) Review (2) Spectroscopy

(1) 1986MOR (2) 1992SPA/MOR

Au–Pd

34.1G5

142.7G21

Review

1986MOR

Au–B

(1) 80.7G3.8 (2) 87.9G2.5

337.8G16 367.8G10.5

MS

(1) 1970MAH/PEE (2) 1971GIN

Au–Al

(1) 77.7G3.1 (2) 77.9G1.5

325G13 325.9G6.3

MS

(1) 1973CUT/FAB (2) 1973GIN/BLU

Au(111, surf.)–Al

w12.9

w54

MBE

1999FIS/BRU

Au–Ga

69.3G3.6

290G15

MS

1972CAR/BER

Au–In

68.4G1.4

286.0G5.7

MS

1989BAL/NUN

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BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

1013

Au(110, 1!2, surf.)–He 0.16 (phys)

0.69

Scattering

1980RIE/ENG

FAu–Xe

w24

w100

Spectroscopy

2004COO/GER

Au–H

(1) (2) (3) (4) (5)

289G13 288.3G8.4 O280 303G13 328

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Au–D

77.0

322.2

Spectroscopy

1979HUB/HER

Au(surf.)–H

!52

!218

Review

1979ERT

Au(110, 2!2, surf.)–H

%58

%243

TPD

1986SAU/MAD

Au–F

(1) 74G5 (2) 70.3

310G21 294.1

(1) Ion reactions (2) Spectroscopy

(1) 1994SCH/HRU (2) 2002OKA/NAK

Au–Cl

(1) (2) (3) (4)

293G63 326 305.7 280G13

(1) (2) (3) (4)

(1) (2) (3) (4)

Au(111, surf.)–Cl

w43

w180

TPD

1993KAS/KOE

Au–Br

(1) 69.1 (2) 51G5

289.3 213G21

(1) FT-MW (2) FT-ICR

(1) 2000EVA/GER (2) 2002BRO/SCH

Au(100, surf.)–Br

59

247

TPD

1980BER/NET

Au–I

(1) 66 (2) 53w65

276 222w272

(1) Spectroscopy (2) FT-ICR

(1) 2001REY/EVA (2) 2002BRO/SCH

69G3 68.9G2 O67 72.4G3.1 78.4

70G15 78 73.1 67G3

Review MS FT-MS Recommend Review

Review FT-Spectrom. FT-MW FT-ICR

1970DAR 1979KAN/MOO 1987CHO/WIL 1991ARM/SUN 2003SCH

1970DAR 1999OBR/ELL 2000EVA/GER 2002BRO/SCH

(continued)

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Table 21.3.1 (continued) BDEs of Au–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Au–O

(1) 54.7G3.5 (2) 51.9G5 (3) 53.3G5

228.9G14.6 217G21 223G21

(1) MS (2) Review (3) Review

(1) 1972SMO/MAN (2) 1983PED/MAR (3) 1990SIM/BEA

Au(surf.)–O

!79

!331

TPD

1994MAD/ROB

Au(100, surf.)–O Au(110, surf.)–O

78.8 81.0

329.7 338.9

Review

2003ZEI

Au(110, 2!2, surf.)–O

%75

%314

TPD

1986SAU/MAD

Au(111, surf.)–O

(1) w56 (2) 75.0

w234 313.8

(1) TPD (2) Review

(1) 1998SAL/PAR (2) 2003ZEI

Au–S

(1) 100G6 (2) 60.6G3.5

418G25 253.6G14.6

MS

(1) 1970GIN(b) (2) 1972SMO/MAN

Au–Se –Te

60.0G3.5 56.7G3.5

251.0G14.6 237.2G14.6

MS

1972SMO/MAN

Au(100, surf.)–N Au(110, surf.)–N Au(111, surf.)–N

101.9 104.8 97.0

426.3 438.5 405.8

Review

2003ZEI

Au–Si

72.8G1.4

304.6G6.0

MS

1979GIN/HAQ

Au–Ge

65.3G3.5

273.2G14.6

MS

1972NEC/SOD

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BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

1015

Au–Sn

(1) 58.4G4 (2) 61.3G1.7

244.3G16.7 256.5G7.2

MS

(1) 1962ACK/DRO (2) 1986KIN/GIN

Au–Pb

31.9G10

133.5G42

Review

1974GUR/KAR

Au–Bi

70G2

293G8.4

Review

1974GUR/KAR

Au(2D)–H2

53

222

Laser ablation

2004AND/WAN

Au(powder)–O2

103

431

Calorimetry

1971DOB/OST

Au(110, 1!2, surf.)–O2 31.5

132

TPD

1986SAU/MAD

Au(111, surf.)–O2

(1) 30 (2) 31 (3) w33

126 130 w138

TPD

(1) 1998SAL/PAR (2) 2000DAV/GOO (3) 2005DEN/MIN

Au–OH

O62.5

O262

FT-MS

1985WEI/WIL

Au(polycs. surf.)–CO

9

38

Review

1964HAY/TRA

Au(film. surf.)–CO

13.1

54.8

Spectroscopy

1972KOT/GRE

Au(110, 1!2, surf.)–CO 10.9

46

IRAS

2003MEI/BUK

Au(110, surf.)–CO

8!

33!

TDS

1987OUT/MAD(c)

Au(332, surf.)–CO

13.1

55

TPD

1996RUG/HOL

Au(surfa./TiO2)–CO

12.5–18.3

52–77

IRAS

2004MEI/GOO

(continued)

7366—CHAPTER 21—5/2/2007—08:23—CRCPAG—15377—XML MODEL B – pp. 967–1026

1016

Comprehensive Handbook of Chemical Bond Energies

Table 21.3.1 (continued) BDEs of Au–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Au(111, surf.)/Pd–CO

32

134

TPD

1994SEL/KOE

TiO2(110, surf.)/ Au–CO

2.7G0.7

11.4G2.8

TPD

1999BON/PAR

Au(110, surf.)–H2O

11–12

46–50

TPRS

1987OUT/MAD(b)

Au–NH3

18.1G1.4

76G6

Derived

2004KOS/SCH

Au2–NH3

O30

O126

Kinetics

1993LIA/HAC

Au–CH3

(1) O27.1 (2) R45.8

O113 R191.6

FT-MS

(1) 1985WEI/WIL (2) 1998CHO/WIL

Au(111, surf.)–CH4

3.5G0.1

14.5G0.2

TDS

1998WET/LAV

Au(100, surf.)–CH3I

7.2G1

30.1G4

TPD/AES

1995YAN/JO

Au(110, surf.)–CH3OH 12

50

TPRS

1987OUT/MAD(b)

Au(polycr. surf.)–C2H2 21

88

Review

1964HAY/TRA

Au(110, surf.)–C2H2

w42

Review

1987OUT/MAD(b)

Au(polycr. surf.)–C2H4 21

88

Review

1964HAY/TRA

Au(110, surf.)–C2H4

w42

Review

1987OUT/MAD(b)

w10

w10

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BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

Au(111, surf.)–C2H4

6.5

27

Au(111, surf.)–C2H6

5.8G0.1

24.1G0.2

Au(110, surf.) –HC(O)OH

13

Au(211, surf.)–C2H4O

1017

TPD

1998WET/LAV

54.4

TDS

1987OUT/MAD

10.3

43.1

TPD

2005KIM/KOE

Au(111, surf.)–C3H4

8.2

34.2

TPD

1998WET/LAV

Au(100, surf.)–C3H6

9.4

39.3

TPD

2000DAV/GOO

Au(111, surf.)–C3H6

(1) 8.4 (2) 9.4

35.0 39.3

TPD

(1) 1998WET/LAV (2) 2000DAV/GOO

Au(111, surf.) –1,3-C4H6

11.0

46.2

TPD

1998WET/LAV

Au(111, surf.) –1-C4H8

9.7G0.1

40.5G0.2

TPD

1998WET/LAV

10.0 10.6

41.8 44.5

TPD

1998WET/LAV

Au(111, surf.) –2-Me-C3H6

10.9

45.4

TPD

1998WET/LAV

Au(111, surf.)–C5H12

12.2

51.1

Au(111, surf.)–C6H12 –C6H14

9.7G0.1 13.5G0.2

40.5G0.2 56.6G0.9

Au(111, surf.) –t-2-C4H8 –iso-2-C4H8

2000LIB/SCO

TPD

1998WET/LAV

(continued)

7366—CHAPTER 21—5/2/2007—08:23—CRCPAG—15377—XML MODEL B – pp. 967–1026

1018

Comprehensive Handbook of Chemical Bond Energies

Table 21.3.1 (continued) BDEs of Au–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Au(111, surf.)–n-C7H16

18.4

77.2

Review

2005LIN/QUI

Au(111, surf.)–c-C6H12

12.1

50.6

TPD

1998WET/LAV

Au–C6H6

O70

O293

FT-ICR

1999HO/DUN

Au(111, surf.)–C6H6

(1) 13.8 (2) 13.8

57.9 57.9

TPD

(1) 1998WET/LAV (2) 2000LIB/SCO

Au(111, surf.) –CH3C6H5

15.8

66.1

TPD

1998WET/LAV

Au(111, surf.) –CD3C6H5

15.8

66.1

TPD

2000LIB/SCO

Au(111, surf.)–C8H16 –C8H18

16.7G0.1 16.8G0.1

69.7G0.3 70.1G0.3

TPD

1998WET/LAV

Au(111, surf.)–c-C8H16

15.1

63.1

TPD

1998WET/LAV

Au(111, surf.)–C9H18 –C9H20

18.0G0.2 18.2G0.2

75.2G0.7 76.2G0.7

TPD

1998WET/LAV

Au(111, surf.)–C10H20 –C10H22

19.1G0.2 19.4G0.2

80.1G0.7 81.1G0.7

TPD

1998WET/LAV

Au(111, surf.)–C11H22

21.0G0.3

87.8G1.3

TPD

1998WET/LAV

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BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

1019

Au(111, surf.)–C12H26

(1) 22.4G0.1 (2) 22.8

93.6G0.5 95.5

TPD

(1) 1998WET/LAV (2) 2000LIB/SCO

Au(surf., 111)–NP NPZnaphtho[2,3-a] pyrene

24.4

102.2

UPS

2004FRA/PAR

Au(111, surf.) –thiophene

14.3

60

TPD

1998WET/LAV

Au(111, surf.)–SR

w48

w203

Derived

1987NUZ/ZEG

Au(111, surf.)–CH3SH

(1) 13.9 (phys.) 58 (2) 11.5 48

TPD

(1) 1990DUB/ZEG (2) 1998LAV/WET

Au(111, surf.)–C2H5SH 13.6 (phys.)

57

TPD

1998WET/LAV

Au(111, surf.)–C2H5SH (1) 30.4 (2) 31.1G1.2

127 130.3G4.8

TPD

(1) 1998LAV/WET (2) 1999LIB/SCO

Au(111, surf.) –2-C3H7SH

15.3 (phys.)

64

TPD

1998LAV/WET

Au(111, surf.) –2-C3H7SH

25.6

107

TPD

1998LAV/WET

Au(111, surf.) –t-C4H9SH

15.3 (phys.)

64

TPD

1998LAV/WET

Au(111, surf.) –t-C4H9SH

25.6

107

TPD

1998LAV/WET

Au(111, surf.)–C4H9SH 16.3 (phys.)

68

TPD

1998WET/LAV

Au(111, surf.)–C4H9SH 30.4

127

TPD

1998LAV/WET

(continued)

7366—CHAPTER 21—5/2/2007—08:23—CRCPAG—15377—XML MODEL B – pp. 967–1026

1020

Comprehensive Handbook of Chemical Bond Energies

Table 21.3.1 (continued) BDEs of Au–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Au(111, surf.) –neo-C5H11SH

16.3 (phys.)

68

TPD

1998LAV/WET

Au(111, surf.) –neo-C5H11SH

30.6–33.7

128–141

TPD

1998LAV/WET

Au(111, surf.) –C6H13SH

8.9 (phys.)

77

TPD

1998WET/LAV

Au(111, surf.) –C6H13SH

29.6

124

TPD

1998LAV/WET

Au(111, surf.) –C8H17SH

20.1 (phys.)

84

TPD

1998WET/LAV

Au(111, surf.) –C8H17SH

29.9–35.1

125 -147

TPD

1998LAV/WET

Au(111, surf.) –C9H19SH

24.6 (phys.)

103

TPD

1998WET/LAV

Au(111, surf.) –C9H19SH –C10H21SH –C12H25SH

30.4–36.3 30.1–34.9 30.4

127–152 126–146 127

TPD

1998LAV/WET

Au(111, surf.) –C14H29SH –C18H37SH

35.9 37.8G2.4

150 158G10

TPD

1998WET/LAV

Au(111, surf.) –C22H45SH

40.4G2.4

169G10

TPD

1998LAV/WET

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BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

1021

Au(111, surf.)–EtSEt

16.3 (phys)

68

TPD

1998LAV/WET

Au(111, surf.)–EtSEt

29.6

124

TPD

1998LAV/WET

Au(nano) –CH2ClCH2SEt –CCl2CH2SEt

10.5G2.2 w11.2

44G9 w47

SPRS

2005PED/DUN

Au(111, surf.)–BuSBu

20.6 (phys)

86

TPD

1998LAV/WET

Au(111, surf.)–sulfides, sulfideZ1, 19.6 (phys) 4-butanedithiol 2,3-butan-edithiol 19.1

82 80

TPD

1998LAV/WET

Au(111, surf.)–sulfides, sulfideZ1, 4-butan-edithiol 28.0 2,3-butanedithiol 25.6 1,6-butanedithiol 30.8–35.9

117 107 129–150

TPD

1998LAV/WET

Au(polycr. surf.)–base baseZadenine guuanine cytosine thymine

136G2 139G2 122G2 104G2

TPD-IRAS

2005OST/LIE

32.5G0.5 33.2G0.5 29.2G0.5 24.9G0.5

21.3.2 AuC–X bonds Table 21.3.2 BDEs of AuD–X Bonds

The broken bonds (boldfaceZdissociated fragment) AuC–Au

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 53.5G4.8 (2) 56.0

223.8G20.3 234.5

Methods (reference in parentheses) (1) Spectrometry (2) Ion mobility

References (1) 1991BIS/MOR (2) 2002GIB/WEI

(continued)

7366—CHAPTER 21—5/2/2007—08:23—CRCPAG—15377—XML MODEL B – pp. 967–1026

1022

Comprehensive Handbook of Chemical Bond Energies

Table 21.3.2 (continued) BDEs of AuC–X Bonds

The broken bonds (boldfaceZdissociated fragment) AuC(Au)x–Au xZ1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 N

AuC(Au)x–Au2 xZ0 1 2 3 4 5 6 7 8 9

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) (1) (1) (1) (1) (1) (2) (1) (2) (1) (1) (2) (1) (1) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (3)

70.6 48.2 63.2 50.0 64.1 46.4 61.1G1.8 69.9 84.4G2.8 40.1 70.1 98.5G3.2 41.7 58.8 103.8G2.5 73.3G2.5 81.1G3.0 69.2G2.8 77.7G2.1 76.1G3.0 86.9G3.0 80.5G3.2 87.4G3.5 78.9G3.0 86.5G2.5 83.7G3.0 87.9G6.0 w79.9

295.3 201.6 264.4 209.4 268.2 193.9 255.7G7.7 292.3 353.1G11.6 167.9 293.3 412.0G13.5 174.6 246.0 434.2G10.6 306.8G10.6 339.6G12.6 289.4G11.6 325.1G8.7 318.4G12.6 363.7G12.6 336.7G13.5 365.7G14.5 330.0G12.6 361.8G10.6 350.2G12.6 367.6G25.1 w334

(1) Ion mobility

(1) 2002GIB/WEI

(2) Re-analyzed

(2) 2003VOG/HAN

(3) Extrapolate

(3) This volume

(1) (1) (1) (1) (1) (1) (1) (2) (1) (1) (2) (1)

74.7 66.9 59.7 61.6 62.7 58.8 64.3 84.4G2.8 58.1 58.6 98.5G3.2 60.2

312.6 279.8 249.9 257.6 262.4 246.0 269.2 353.1G11.6 243.1 245.1 412.0G13.5 251.8

(1) Ion mobility

(1) 2002GIB/WEI

(2) PD

(2) 2002VOG/HAN

7366—CHAPTER 21—5/2/2007—08:23—CRCPAG—15377—XML MODEL B – pp. 967–1026

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

10

1023

(1) 48.9 (2) 103.8G2.5 (2) 98.9G2.8

204.5 434.2G10.6 413.9G11.6

AuC–Xe

31G3

130G13

Derived

1998SCH/SCH

AuC–Be

95.8G7

401G29

Derived from IP in ref.

2004BAL/CIO

AuC–Al

40.7G7

170G30

Derived from IP in ref.

1996NIST

AuC–H

34.3

143.5

Review

1990OHA/GOD

AuC–F

19

79

Review

2003SCH

AuC–I

(1) O60 (2) 55w67

O251 230w280

(1) Ion reactions (2) FT-ICR

(1) 1995SCH/HRU (2) 2002BRO/SCH

AuC–B

(1) 85G15 (2) 79G12

356G63 329G50

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

AuC–Ge

70G5.8

292G24

Derived from IP in ref.

1996NIST

AuC–CH2

(1) R95 R397 (2) %88.9G0.7 %372G3 (3) 92–95 385–398

(1) FT-MS (2) PD (3) Review

(1) 1987CHO/WIL (2) 2000AGU/HUS (3) 2004MET

AuC–CH3

O55.9

O234

FT-MS

1987CHO/WIL

AuC–C2H4

(1) O32.7 (2) 69 (3) 82.3

O137 289 344.5

(1) FT-MS (2) Review (3) PD

(1) 1987CHO/WIL (2) 1998SCH/SCH (3) 2004STR/CIT

12

(continued)

7366—CHAPTER 21—5/2/2007—08:23—CRCPAG—15377—XML MODEL B – pp. 967–1026

1024

Comprehensive Handbook of Chemical Bond Energies

Table 21.3.2 (continued) BDEs of AuC–X Bonds

The broken bonds (boldfaceZdissociated fragment) AuC–C3H6

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(1) 70G7 (2) O75 (2) O75

293G29 O314 O314

(1) Derived (2) GIB MS

(1) 1998SCH/SCH (2) 1995SCH/HRU

(1) (2) (3) (4) (3) (2)

w293 289G29 O293 256 129.7 142G13

(1) (2) (3) (4)

(1) (2) (3) (4)

(1) 38G4 (2) 39.2G2.3 (2) 46.1G4.6

159G17 164.0G9.6 193.0G19.3

(1) Derived (2) CID

(1) 1998SCH/SCH (2) 2001POI/PRA

AuC–CO

48G2

201G8

Derived

1998SCH/SCH

AuC(Au)x–CO xZ4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24

23.8G2.3 25.1G2.3 24.7G2.3 20.5G2.3 19.6G2.3 20.8G2.3 20.8G2.3 20.1G2.3 19.8G2.3 19.8G2.3 20.3G2.3 19.8G2.3 18.4G2.3 19.6G2.3 19.4G2.3 18.0G2.3 18.7G2.3 16.4G2.3 15.2G2.3 16.1G2.3 16.1G2.3

99.4G9.6 105.2G9.6 103.2G9.6 85.9G9.6 82.0G9.6 86.8G9.6 86.8G9.6 83.9G9.6 83.0G9.6 83.0G9.6 84.9G9.6 83.0G9.6 77.2G9.6 82.0G9.6 81.0G9.6 75.3G9.6 78.2G9.6 68.2G9.6 63.7G9.6 67.5G9.6 67.5G9.6

FT-ICR

2005NEU/WEI

–C4H6

AuC–C6H6

–C6F5H –C6F6

AuC(H2O)x–H2O xZ0 1

w70 69G7 O70 61.1 31.0 34G3

GIB MS Derived FT-ICR FT-MS

7366—CHAPTER 21—5/2/2007—08:23—CRCPAG—15377—XML MODEL B – pp. 967–1026

1995SCH/HRU 1998SCH/SCH 1999HO/DUN 2000SCH/BRO

BDEs of Cu(CuG)–, Ag(AgG)–, and Au(AuG)–X Bonds

25–28 29 30 31 32–39 40 41–46 47 48 49–64

1025

!15.0 16.8G2.3 17.3G2.3 15.9G2.3 !15.0 15.0G2.3 !15.0 17.1G2.3 17.1G2.3 !15.0

!62.7 70.4G9.6 72.4G9.6 66.6G9.6 !62.7 62.7G9.6 !62.7 71.4G9.6 71.4G9.6 !62.7

AuC–H2S –NH3 –PH3

55G6 71G7 96G8

230G25 297G29 402G33

Derived

1998SCH/SCH

AuC–CH3CN –CH3NC –CH3SCH3

68G7 71G7 80G8

285G29 297G29 335G33

Derived

1998SCH/SCH

AuC 8 –MeOH

8.1

33.8

PD

2002VOG/HAN

21.3.3 AuK–X bonds Table 21.3.3 BDEs of AuL–X Bonds

The broken bonds (boldfaceZdissociated fragment) AuK–Au

AuK(Au)x–Au xZ1 2 3 4 5

BDEs (boldfaceZrecommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

References

(1) 45.2G3.5 (2) 44.7 (3) %77.3

189.0G14.5 187.0 %323

(1) PES (2) Derived (3) CID

(1) 1990HO/ERV (2) 1996SMI/YAT (3) 2000SPA/SHI

(1) %91.3 (1) %50.7 (1) %60.4 (1) %62.5 (2) 51.1 (1) %64.8 (2) 64.3

%382 %212 %253 261 214 271 269

(1) CID

(1) 2000SPA/SHI

(2) TRPD

(2) 2000SPA/SHI

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 21.3.3 (continued) BDEs of AuK–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZrecommended data; reference in parentheses) kcal/mol

kJ/mol

AuK(Au)x–Au xZ13 16 N

(1) 59.2 (1) 87.6 (2) w79.9

248 367 w334

AuK–Ag

25.6G3.6

AuK–O –S

Methods (reference in parentheses)

References

(1) PD

(1) 2006HER/SCH

(2) Extrapolate

(2) This volume

107G15

Derived from EA in ref.

1996NIST

54.8G5 103.6G6

229.3G21 433.4G25

Derived from EA in ref.

2005ICH/GIA

AuK–C6F6

24G4

100G17

FT-ICR

1999HO/DUN

AuK(Au)–CO

21.0

87.8

PES

2002LUT/PON

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chapter twenty-two

BDEs of Zn(ZnC)–, Cd(CdC)–, and Hg(HgC)–X bonds 22.1 Zn– and ZnC– X bonds 22.1.1 Zn–X bonds Table 22.1.1 BDEs of Zn–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Zn–Zn

(1) (2) (3) (4) (5)

Zn–Hg

4.8G0.6 5.3G1.5 5.3 2.2 1.7

Methods (reference in parentheses)

kJ/mol

Viscosity Review Review Spectroscopy Review

References

19.9G2.5 22.2G6.3 22.2 9.1 7.0

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

1964CAR/KUS 1974GUR/KAR 1979MIE/GIN 1984SU/LIA 1996SMI/YAT

1.8

7.3

Spectroscopy

1992SUP/KED

Zn–K

1.6

6.5

Spectroscopy

1984CZU/REB

Zn–In

7.7

32.2

Review

1967DRO/GOL

Zn–Ne

(1) 0.95 (2) 0.94

3.96 3.92

(1) Spectroscopy (2) Spectroscopy

(1) 1999MCC/BEL (2) 2000KOP/CZA

(continued)

1027

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Table 22.1.1 (continued) BDEs of Zn–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Zn–Ar

(1) 1.8 (2) 1.2

7.4 5.0

(1) Spectroscopy (2) Review

(1) 1990BEN/BRE (2) 1994CZA/KRA

Zn(surf.)–Ar

1.6

6.6

Calorimetry

1962CHO/FIS

Zn–Kr

1.2

5.0

Spectroscopy

1992WAL/RYT

Zn–H –D

20.5G0.5 21.2

85.8G2 88.7

Spectroscopy

1979HUB/HER

HZn–H

76.1 at 0 K

318.4

Derived

2005SHA/YU

Zn(surf.)–H

25.8–27.4

108–115

Electrochemical

1996CHA/RIN

Zn(polycs. surf.)–H

33–37

138–155

Electrochemical

1970KRI

p-InP(solid)/Zn–H

27.7G2.3

115.8G9.6

Kinetics

1992PEA/HOB

[ZnO(0001, surf.)/Zn]–H

23.7

99

LEED

2002BEC/HOV

[ZnO(0001, surf.)/O]–H

39.0

163

LEED

2003KUN/BUR

Zn–F

87G15

364G63

Review

1974GUR/KAR

Zn(Cl)x–Cl xZ0

(1) 54.7G0.7

228.7G2.9

(1) Spectroscopy

(1) 1967COR/LYN

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BDEs of Zn(ZnC)–, Cd(CdC)–, and Hg(HgC)–X Bonds

1029

(2) 54.7G2 (3) 87G5

229G8 364G21

(2) MS (3) Derived from DfH0 in ref.

(2) 1999HIL/LAU (3) 2002CRC

Zn–Br

33G7

138G29

Review

1974GUR/KAR

Zn–I

(1) 26.2G0.4 (2) 36.6G1.5

109.7G1.7 153.1G6.3

(1) Spectroscopy (2) Equilibrium

(1) 1992JOR/LIP (2) 2003HIL/LAU(b)

Zn–O

(1) (2) (3) (4) (5)

280.1 !267G42 159.0G3.8 %226 %250

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Zn–S –Se –Te

53.7G3 40.8G6.2 28.1G4.3

224.8G12.6 170.7G25.9 117.6G18.0

Derived

1982GRA/HIR

Zn(1000, surf.)–H2

18

75.3

XPS

1985CHA/GRI

ZnO(powder)–H2

12.6G1

52.7G4

TPD

1982GRI/YAT

ZnO(polycs. surf.)–O2

110

460

Review

1964HAY/TRA

ZnO(polycs. surf.)–CO

(1) 9–13 (2) 12.2

38–54 51.0

(1) Review (2) Combined

(1) 1964HAY/TRA (2) 1982GRI/YAT(b)

ZnO(1010, surf.)–CO

12

50

PES

1993SOL/JON

36.2

Mol. beam

2005WAN/BUR

1

ZnO(1000, surf.)/Zn/H–CO2 8.7

66.9 !63.8G10 38.0G0.9 %54 %59.8

Derived Review GIB MS HT MS MS

1982GRA/HIR 1983PED/MAR 1991CLE/DAL 1993WAT/THI 2003MAK/ZBE

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 22.1.1 (continued) BDEs of Zn–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

ZnO(1000, surf.)/Zn–CO2

8.2 (pristine)

34.4

TDS

2005WAN/HOK

ZnO(1000, surf.)/Zn–CO2

10.4 (defected) 43.6

TDS

2005WAN/HOK

(1) (2) (3) (4) (5)

22 19.4G3.2 24.5G4.0 16.7G2.3 20.8G4

92 81.2G13.4 102.5G16.7 70G10 86.9G17

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

(1) (2) (3) (5)

66 69.4G3.2 63.7G1.5 67.4G4

276 290G14 266.5G6.3 282G17

Zn(CH3)x–CH3 xZ0

1

Review Ion beam Kinetics Review Derived from DfH0 in ref.

1983SMI/PAT 1986GEO/ARM 1989JAC 1996ARM/KIC 1996NIST

ZnO-Zn(0001, surf.)–H2CO

32

133.9

Re-analysis

2001MAD/IDR

ZnO(polycs. surf.)–C2H4

25.2

105

Review

1964HAY/TRA

(1) 16 (2) 22.0G4.2 (3) 17.8G4.2

67 92.0G17.6 74.3G17.6

(1) Review (2) Kinetics (3) Derived from DfH0 in ref.

(1) 1983SMI/PAT (2) 1989JAC (3) 1996NIST

(1) 55 (2) 52.4G2.0 (3) 56.2G4.2

230 219.2G8.4 235.1G17.6

22.0G4.2 52.4G2.0

92.0G17.6 219.2G8.4

Review

1993ZHA/JAC

26.8

112

TDS

2000HOV/KOL

Zn(C2H5)x–C2H5 xZ0

1

Zn(C3H7)x–C3H7 xZ0 1

ZnO(0001, surf.)/Zn– pyridine

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BDEs of Zn(ZnC)–, Cd(CdC)–, and Hg(HgC)–X Bonds

1031

22.1.2 ZnC–X bonds Table 22.1.2 BDEs of ZnD–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

ZnC–Zn

(1) 13.8G4.6 (2) 10.6 (3) 14.4G4.6

57.7G19.3 44.2 60G19.3

(1) FT-MS (2) Review (3) Der. from IP in ref.

(1) 1988BUC/GOR(b) (2) 1996SMI/YAT (3) 1996NIST

ZnC–Ar

(1) 8.3 (2) 6.8G0.3

34.8 28.7G1.2

(1) GDMS (2) R2PI

(1) 1995BAR/SMI (2) 1999LEU/BEL

ZnC–H

(1) 54.4G3 (2) 51.7G3.7

228G13 216G15

GIB MS

(1) 1988GEO/ARM (2) 1995KIC/ARM

3.8G0.4, at 0 K 2.8G0.4 2.4G0.4 1.6G0.4 1.5G0.4 w1.4

15.7G1.7

Equilibrium

1997WEI/KEM

11.5G1.7 9.8G1.7 6.7G1.7 6.3G1.7 w5.9

(1) 70.6G3.2 (2) 66.9G1.6 (3) 27.5G1

295G14 280G7 115G4

(1) Ion beam (2) Review (3) Review

(1) 1986GEO/ARM (2) 1996ARM/KIC (3) 1990SIM/BEA

ZnC–O

(1) 25–40 (2) 38.5G1.2

105–167 161.1G4.8

(1) ICR (2) GIB MS

(1) 1981KAP/STA (2) 1991CLE/DAL

ZnC–OH

30.4

127.2

TQ MS

1989MAG/DAV(b)

ZnC(H2)x–H2 xZ0 1 2 3 4 5

ZnC(CH3)x–CH3 xZ0 1

References

(continued)

7366—CHAPTER 22—6/2/2007—13:05—CRCPAG—15378—XML MODEL B – pp. 1027–1040

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Comprehensive Handbook of Chemical Bond Energies

Table 22.1.2 (continued) BDEs of ZnC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

ZnC–H2O

(1) 39.0 (2) 39.0

163.2 163

(1) TQ MS (2) ES MS

(1) 1989MAG/DAV(b) (2) 2000VUK/STO

ZnC–NO

18.2G2.3

76.2G9.6

CID

1991CLE/ARM

ZnC–pyridine

59.3G1.6

248.1G6.9

CID

2002ROD/STA

ZnC–pyrimidine

50.1G1.8

209.6G7.7

CID

2001AMU/ROD

ZnC–adenine

R57.9G1.5

R242.2G6.4 CID

2002ROD/ARM

ZnC–imidazole

60.3G2.3

252.5G9.7

CID

2004RAN/AMU

ZnC–Si –SiH –SiH2 –SiH3

65.5G2.3 77.7G2.5 38.0G2.1 71.7G3.5

274.1G9.6 325.1G10.5 159.0G8.8 300.0G14.6

GIB MS

1995KIC/ARM

ZnC–S

47.3G2.8

198G12

GIB MS

2002RUE/ARM

ZnC–CS

(1) 33.7G2.2 (2) 35.5G5.5

141G9 149G23

GIB MS

(1) 2000ROD/ARM(b) (2) 2002RUE/ARM

9.6G0.3 8.6G0.3

40.2G1.3 36.0G1.3

ES MS

2005LIU/SEU

[OT-Zn]C(H2O)x–H2O xZ0 1 OTZoxytocin

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BDEs of Zn(ZnC)–, Cd(CdC)–, and Hg(HgC)–X Bonds

1033

Zn2C(L)x–L, LZ MeCOMe xZ5 6

17.4 14.4

72.8 60.2

ES MS

2000PES/BLA

Zn2C(L)x–L LZN-methylacetamide xZ4 5 6

25.1 22.9 20.8

105.0 95.8 87.0

ES MS

2000PES/BLA

22.2 Cd– and CdC–X bonds 22.2.1 Cd–X bonds Table 22.2.1 BDEs of Cd–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Cd–Cd

(1) (2) (3) (4) (5)

3.1G0.2 2.9 2.0 1.76 w2.06

Cd–Ne

0.95

Cd–Ar

Cd–Kr

kJ/mol

Methods (reference in parentheses)

12.9G0.8 12.2 8.3 7.36 w8.62

(1) (2) (3) (4) (5)

3.97

Spectroscopy

1994CZA/KRA

(1) 1.2 5.0 (2) 1.33G0.01 5.57G0.05

(1) Review (2) Spectroscopy

(1) 1994CZA/KRA (2) 2002KOP/LUK

(1) (2) (3) (4)

Spectroscopy

(1) (2) (3) (4)

1.26G0.03 1.26 1.19 1.23

5.27G0.12 5.26 4.98 5.17

Viscosity Review Spectroscopy Spectroscopy Spectroscopy

References (1) (2) (3) (4) (5)

1964CAR/KUS 1979MIE/GIN 1984SU/LIA 1985KOW/CZA 1986BOU

1986BOU 1988WAL/BEN 1991CZA/BOB 1992WAL/RYT (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 22.2.1 (continued) BDEs of Cd–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Cd–Xe

(1) 1.39 (2) 1.56

5.82 6.54

Spectroscopy

(1) 1989FUN/BRE (2) 1994CZA/KRA

Cd–Na

2.4

10.2

Spectroscopy

1973ZOL

Cd–K

1.7

7.3

Spectroscopy

1984CZU/REB

Cd–B

71.9

301.0

MS

1979HUB/HER

Cd–In

32

134

Review

1974GUR/KAR

Cd–H

16.5G0.1

69.0G0.4

Review

1990SIM/BEA

HCd–H

70.7 at 0 K

295.8

Derived

2005SHA/YU

Cd(polycs. surf.)–H

28–29

117–121

Electrochemical

1970KRI

GaAs(solid)Cd–H

31.1G2.3

130.3G9.6

PACS

1991PFE/DEI

p-InP(solid)Cd–H

32.3G2.3

135.1G9.6

Kinetics

1992PEA/HOB

Cd–F

73G5

305G21

MS

1965BES/KAN

Cd–Cl

49.8

208.4

MS

1979HUB/HER

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BDEs of Zn(ZnC)–, Cd(CdC)–, and Hg(HgC)–X Bonds

1035

Cd–Br

38G23

159G96

Review

1968GAY

Cd–I

(1) 33G5 (2) 23.2G0.5

138G21 97.2G2.1

(1) Review (2) Spectroscopy

(1) 1974GUR/KAR (2) 1992JOR/LIP

Cd–O

(1) 55.0 (2) 56.4G20

230.3 236G84

(1) Derived (2) Review

(1) 1982GRA/HIR (2) 1990SIM/BEA

Cd–S –Se –Te

49.8G5 30.5G6 23.9G3.6

208.5G20.9 127.6G25.1 100.0G15.1

Derived

1982GRA/HIR

(1) 13 (2) 15.2G2.4 (3) 11.9G4

54 63.6G10.0 49.8G17

(1) 1983SMI/PAT (2) 1989JAC (3) 1996NIST

(1) 58 (2) 56.0G1.5 (3) 60G4

243 234.3G6.3 250G17

(1) Review (2) Kinetics (3) Derived from DfH0 in ref.

Cd(CH3)x–CH3 xZ0

1

22.2.2 CdC–X bonds Table 22.2.2 BDEs of CdD–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CdC–Cd

29.3G2.4

122.5G10

Derived from IP in ref.

1996NIST

CdC–H

(1) 48.5 (2) 42.9

203 179.5

Review

(1) 1985SKI/CON (2) 1990OHA/GOD (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 22.2.2 (continued) BDEs of CdC–X Bonds

The broken bonds (boldfaceZdissociated fragment) CdC(CH3)x–CH3 xZ0 1

CdC–C6H6

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(1) 54 (2) 54.5G0.7 (2) 26.1G0.7

226 228G3 109G3

Review

(1) 1985SKI/CON (2) 1990SIM/BEA

32.5G4.6

136G19

Kinetics

1997HO/YAN

22.3 Hg– and HgC–X bonds 22.3.1 Hg–X bonds Table 22.3.1 BDEs of Hg–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Hg–Hg

(1) (2) (3) (4) (5)

Hg–Zn

2.7G0.5 2G0.5 2.2 1.88G0.06 1.94G0.04

kJ/mol

Methods (reference in parentheses) Review MS Spectroscopy Spectroscopy Spectroscopy

References

11.3G2 8G2 9.0 7.85G0.24 8.10G0.18

(1) (2) (3) (4) (5)

1.8

7.3

Spectroscopy

Hg–Li

(1) 3.3 (2) 3.14G0.09

13.8 (1) Review 13.16G0.38 (2) Spectroscopy

(1) 1979HUB/HER (2) 1995GRU/LI

Hg–Na

(1) 2.5 (2) 2.6 (3) 2.6

10.5 10.8 10.8

(1) 1973ZOL (2) 1982HUN/MAI (3) 1991CZU/REB

(1) Spectrometry (2) Scattering (3) Spectroscopy

7366—CHAPTER 22—6/2/2007—13:05—CRCPAG—15378—XML MODEL B – pp. 1027–1040

(1) (2) (3) (4) (5)

1974GUR/KAR 1982HIL 1984SU/LIA 1987ZEH 1994KOP/ATK

1992SUP/KED

BDEs of Zn(ZnC)–, Cd(CdC)–, and Hg(HgC)–X Bonds

1037

Hg–K

(1) 2 (2) 2.4 (3) 2.1

8.4 9.9 8.8

(1) Review (2) Spectroscopy (3) Scattering

(1) 1974GUR/KAR (2) 1984CZU/REB (3) 1986LAC/MAI

Hg–Rb

2

8.4

Review

1979HUB/HER

Hg–Cs

2

8

Derived

1973LIT/SPA

Hg–He

(1) 1.58 (2) 0.9

6.61 3.8

(1) Review (2) Spectroscopy

(1) 1974GUR/KAR (2) 1988YAM/ISO

Hg–Ne

(1) 1.0 (2) 1.09 (3) 0.99

4.2 4.56 4.14

Spectroscopy

(1) 1988YAM/ISO (2) 1995OND/YAM (3) 1997TAS/OND

Hg–Ar

(1) (2) (3) (4)

5.29 O9.7 5.20 5.32

Spectroscopy

(1) (2) (3) (4)

Hg–Kr

(1) 1.4 (2) 2.69 (3) 1.37

5.8 11.2 5.75

(1) FIL (2) Review (3) Spectroscopy

(1) 1987KAY/FUK (2) 1999GIL/TRA (3) 2001KOP/ATK

Hg–Xe

1.59

6.65

LIF

1986YAM/FUK

Hg–H –D –T

9.523 10.05 10.31

39.844 42.05 43.14

Spectroscopy

1979HUB/HER

HHg–H

73.9 at 0 K

309.2

Derived

2005SHA/YU

Hg(polycs. surf.)–H

29

121

Electrochemical

1970KRI

1.26 O2.3 1.24 1.27

1988YAM/ISO 1990OHS/LID 1997TAS/IND 2002KOP/CZA

(continued)

7366—CHAPTER 22—6/2/2007—13:05—CRCPAG—15378—XML MODEL B – pp. 1027–1040

1038

Comprehensive Handbook of Chemical Bond Energies

Table 22.3.1 (continued) BDEs of Hg–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Hg–F FHg–F

(1) w43 (2) 90.9

w180 380.3

(1) Spectroscopy (2) Derived from DfH0 in ref.

(1) 1979HUB/HER (2) 1996NIST

Hg–Cl ClHg–Cl

(1) 24G2 (2) 22.0G2.2 (3) 82.7

100G8 92.0G9.2 346.0

(1) Spectroscopy (2) PI (3) Derived from DfH0 in ref.

(1) 1968GAY (2) 1983LIN/BRO (3) 1996NIST

Hg–Br BrHg–Br

(1) 17.9 (2) 72.0

74.9 301

(1) Spectroscopy (2) Derived from DfH0 in ref.

(1) 1993LIP/JOR (2) 1996NIST

Hg–I IHg–I

(1) 8.29G0.23 (2) 61.3

34.69G0.96 (1) Spectroscopy 256.3 (2) Derived from DfH0 in ref.

(1) 1993JOR/BAS (2) 1996NIST

Hg–O

(1) 52.8 (2) 50.9 (3) 64.2

221.1 213 269

(1) 1982GRA/HIR (2) 1990SIM/BEA (3) 1996NIST

Hg–S

51.9G5.3

217.3G22.2 Derived

1982GRA/HIR

Hg–Se

34.5G7.2

144.3G30.1 Derived

1982GRA/HIR

Hg–Te

%34

%142

Review

1974GUR/KAR

Hg–Tl

(1) 1 (2) 0.7

4 2.9

Est. by exp.

(1) 1950HER (2) 1973LIT/SPA

(1) Derived (2) Review (3) Derived from DfH0 in ref.

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BDEs of Zn(ZnC)–, Cd(CdC)–, and Hg(HgC)–X Bonds

Hg(CH3)x–CH3 xZ0

1

(1) (2) (3) (4)

2G2 3 5.4G3.0 1.9G4

8G8 13 22.6G12.6 7.8G17

(1) (2) (3) (4)

%57.5 59 57.2G1.5 60.4G5

%241 247 239.3G6.3 252.7G21

1039

(1) Kinetics (2) Review (3) Kinetics (4) Derived from DfH0 in ref.

(1) (2) (3) (4)

1969KOM/PRI 1983SMI/PAT 1989JAC 1996NIST

ClHg–CH3 BrHg–CH3 IHg–CH3

67.0G3 64.5G9 61.8G3

280.0G12.6 Derived from 270G38 DfH0 in ref. 258.6G12.6

1996NIST

ClHg–C2H5 BrHg–C2H5 IHg–C2H5

63.3G3 60.5G9 56.9G3

264.8G12.6 Derived from 253G38 DfH0 in ref. 238.1G12.6

1996NIST

(1) 6.5 (2) 3 (3) 4.6G10

27.2 13 19G42

(1) 1971LAL/PRI (2) 1983SMI/PAT (3) 1996NIST

(1) 43.7 (2) 48 (3) 44.9G10

182.8 201 188G42

Hg(C2H5)x–C2H5 xZ0

1

(1) Pyrolysis (2) Review (3) Derived from DfH0 in ref.

22.3.2 HgC–X bonds Table 22.3.2 BDEs of HgD–X Bonds The broken bonds (boldfaceZdissociated fragment) HgC–Hg

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) 32.7G0.5 (2) 32 (3) 23

kJ/mol 137.0G1.9 134 96

Methods (reference in parentheses) (1) PI (2) EI (3) Review

References (1) 1984LIN/LIA (2) 1990HAB/KOR (3) 1996SMI/YAT (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 22.3.2 (continued) BDEs of HgC–X Bonds

The broken bonds (boldfaceZdissociated fragment) HgC(Hg)x–Hg xZ4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

4.6 5.3 4.8 4.8 4.8 4.8 5.3 6.2 6.5 6.7 6.9 7.1 7.8 8.3 8.8 9.7 10.2 10.6 11.1 11.3 w14.2

Methods (reference in parentheses)

kJ/mol 19.2 22.2 20.1 20.1 20.1 20.1 22.2 25.9 27.2 28.0 28.9 29.7 32.6 34.7 36.8 40.6 42.7 44.4 46.4 47.3 w59

References

(1) EI

(1) 1990HAB/KOR

(2) Extrapolate

(2) This volume

HgC–Ar

(1) 4.7G0.4 (2) 5.3G0.3

19.5G1.6 22.2G1.2

PI

(1) 1972BRI (2) 1985LIN/BRO

HgC–Kr

9.1G0.3

37.9G1.3

PI

1986LIA/NG

HgC–Xe

17.2G0.3

72.2G1.3

PI

1986LIA/NG

HgC–H

(1) 69 (2) 49.5

289 207

Review

(1) 1985SKI/CON (2) 1990OHA/GOD

(1) 70 (2) 68G0.7 (2) 22.9G0.7

293 285G3 96G3

Review

(1) 1985SKI/CON (2) 1990SIM/BEA

HgC(CH3)x–CH3 xZ0 1

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chapter twenty-three

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X bonds 23.1 B–, BC–, and BK–X bonds 23.1.1 B–X bonds Table 23.1.1 BDEs of B–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

B–B

(1) 65.5 (2) 69.3

274 290

F2B–BF2 Cl2B–BCl2

(2) 78.9 (2) 60.2

330 252

(OB)–BO

110G10

BH3–BH3

B–Sc –Y

Methods (reference in parentheses)

References

(1) Review (2) Derived from DfH0 in ref.

(1) 1996SMI/YAT (2) 1996NIST

460G42

Review

1967DRO/GOL

(1) %38.3 (2) 36G3 (3) 41.2

%160.2 150.6G12.6 172

(1) Re-anal. (2) Pyrolysis (3) Derived from DfH0 in ref.

(1) 1964GAR/BEN (2) 1969FEH/MAP (3) 1996NIST

65G15 69G15

272G63 289G63

Review

1974GUR/KAR (continued)

1041

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Comprehensive Handbook of Chemical Bond Energies

Table 23.1.1 (continued) BDEs of B–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

–La

80G15

335G63

B–Ce

72.9G5

305G21

MS

1970GIN

B–Th

71G8

297G33

MS

1969GIN

B–U

77G8

322G33

MS

1970GIN

B–Ti

65G15

272G63

Review

1974GUR/KAR

B–Ru

106.8G5

446.9G21

MS

1970MAH/PEE

B–Rh –Ir

113.7G5 122.4G4

475.8G21 512.2G17

MS

1970MAH/PEE

B–Pd

(1) 78.6G5 (2) 84G4

329.0G21 351.5G16.7

(1) MS (2) Review

(1) 1970MAH/PEE (2) 1974GUR/KAR

B–Pt

114.2G4

477.8G16.7

MS

1968MCL/MAH

B–Au

(1) 80.7G3.8 (2) 87.9G2.5

337.8G16 367.8G10.5

MS

(1) 1970MAH/PEE (2) 1971GIN

B–Cd

71.9

301.0

MS

1979HUB/HER

B–Ne

0.95

3.97

LIF

1996YAN/HWA

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BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

B–Ar

BN(surf.)–Ar

BN(surf.)–Kr

BN(surf.)–Xe

B(H)x–H xZ0

1

2

(1) 1.18

4.94

(2) 1.10

4.62

(1) 2.1 (2) 2.0 (3) 2.1

9.0 8.2 8.6

(1) Adsorption (2) Adsorption (3) Virial anal.

(1) 1958ROS/PUL (2) 1962PIE (3) 1979LEV/RYB

(4) 2.1G0.1

8.7G0.5

(4) Review

(4) 1991VID/IHM

(1) 2.6

10.9

(1) Virial anal.

(1) 1979LEV/RYB

(2) 2.5

10.5

(2) Review

(2) 1991VID/IHM

(1) 3.3

13.7

(1) Virial anal.

(1) 1979LEV/RYB

(2) 3.4

14.2

(2) Review

(2) 1991VID/IHM

(1) (2) (3) (1) (4)

351.2 340 345.2G2.5 376.3 460

(1) Derived (2) Spectroscopy (3) Review

(1) 1973LIT/SPA (2) 1988PIA/OBR (3) 1990BAU/LAN

(4) Derived from DfHo in ref.

(4) 1996NIST

83.9 81.3 82.5G0.6 89.9 109.9

Spectroscopy

1043

(1) 1997YAN/DAG (2) 1998STA/KNI

(1) 82.6 (4) 74.6

345.4 312

B–D

(5) 81.5G1.5

341.0G6.3

(5) Review

(5) 1974GUR/KAR

B(O)–H

99.5

416

Derived from DfH0 in ref.

1998CHA

B(O)O–H B(S)–H

118 98.2

494 411

Derived from DfH0 in ref.

1996NIST

F2B–H

86.5

362

Derived from DfH0 in ref.

1996NIST (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 23.1.1 (continued) BDEs of B–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Si(solid)B–H

29.5G0.7

123.5G2.9

Kinetics

1989ZUN/WEB

B2H5–H

%102.7

%429.7

PIMS

1989RUS/SCH

(1) (2) (3) (3) (4)

757 757.4G0.8 732 569 553

(1) MS (2) Revised (3) Review

(1) 1980LAU/HIL (2) 1998MAR/TAY (3) 2001HIL/LAU

(4) Derived from DfH0 in ref.

(4) 1996NIST

B(F)x–F xZ0

1

2

181 181.0G0.2 175 136 132.3

(3) 150 (4) 149.4

628 625

B(H)x–F xZ1 2

145.5G6 144.4G6

609G25 604G25

Derived from DfH0 in ref.

1996GUR/VEY

(OB)–F

163

682

Derived from DfH0 in ref.

1998CHA

B(F)(O)–F

75

314

Derived from DfH0 in ref.

1996NIST

(1) 122.2G1.1 (2) 129

511.3G4.6 540

(1) 1996HIL (2) 1996NIST

(3) (2) (3) (2) (3)

427 342 389 445 460

(1) MS (2) Derived from DfH0 in ref. (3) Derived

B(Cl)x–Cl xZ0

1 2

102 81.8 93 106.3 110

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(3) 2001HIL/LAU

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

B(O)–Cl –Br

1045

104.6 86.7

438 363

Derived from DfH0 in ref.

1998CHA

(1) 94.6 (2) 104.6

396 438

(1) 1991BHA/BHA (2) 1996NIST

(3) 93.4G0.1 (2) 67.7 (2) 89.7

390.9G0.5 283 375

(1) Spectroscopy (2) Derived from DfH0 in ref. (3) Spectroscopy

B(I)x–I xZ0 1 2

86.4 40.5 66.5

361 170 278

Derived from DfH0 in ref.

1996NIST

B(X)–O XZF Cl Br

175.9 169 176.6

736 707 739

Derived from DfH0 in ref.

1996NIST

(1) 192.7G1.2 (2) 193.4

806.3G4.9 809

(1) 1970UY/DRO (2) 1998CHA

(2) 127.6

534

(1) MS (2) Derived from DfH0 in ref.

B(F)2–O

118.6

496

Derived from DfH0 in ref.

1996NIST

(HB)–O

212.8

890

Derived from DfH0 in ref.

1996NIST

HOB–O

146.2

611.5

Derived from DfH0 in ref.

1996NIST

B(Br)x–Br xZ0

1 2

B(O)x–O xZ0

1

(3) 1998HUN/FAN

(continued)

7366—CHAPTER 23—3/2/2007—12:00—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

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Comprehensive Handbook of Chemical Bond Energies

Table 23.1.1 (continued) BDEs of B–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

OBB–O OBOB–O

191.6 150.4

801.5 629.1

B(OH)x–OH xZ0 1 2

(1) 144.3G7 (2) 121.3G7 (2) 132.1G7

604G30 508G30 553G30

Derived from DfH0 in ref.

(1) 1996GUR/VEY (2) 1998CHA

B(O)–OH B(O)–OBO

142.9 131.4

598 550

Derived from DfH0 in ref.

1998CHA

B–O(B)x xZ0

(1) 191G3

799G13

(1) 1996GUR/VEY

1

(2) 113G15

473G63

Derived from DfH0 in ref.

(1) 143 (2) 137.9G2.2 (3) 160

598 577G9.2 669

(1) MS (2) MS (3) Derived from DfH0 in ref.

(1) 1970GIN(b) (2) 1970UY/DRO (3) 1996NIST

B(O)–OCH3

115G26

481G109

Derived from DfH0 in ref.

1987HET/COL

BH3–S(CH3)2

25.9

108.4

Derived

1998REN/WOR

B–Se –Te

110.4G3.5 84.7G4.8

462G14.6 354G20

MS

1970UY/DRO

B(H)x–S xZ0 1

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(2) 1998CHA

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1047

B–N

(1) 93G5 (2) 90.3G2.1

389G21 377.9G8.7

(1) Review (2) Spectroscopy

(1) 1970DAR (2) 1999RED/AHA

B–P

82.9G4

347G16.7

MS

1972GIN

BN(surf.)–N2

2.2

9.2

Adsorption

1958ROS/PUL

H3B–NH3 –NH2(CH3) –NH(CH3)2 –N(CH3)3

(1) (1) (1) (1) (2)

130.1G4.2 146.4G3.3 152.3G4.2 145.6G2.1 160.2

Derived

(1) 1989HAA

(CH3)3B–NH3 –NH2(CH3) –NH(CH3)2 –N(CH3)3

13.8G0.3 17.6G0.2 19.3G0.2 17.6G0.2

57.7G1.3 73.6G0.8 80.8G0.8 73.6G0.8

Re-anal.

1989HAA

(CH3)3B–(cycloCH2CH2N)H –(cycloCH2CH2CH2N)H –NH2(C2H5) –NH(C2H5)2 –N(C2H5)3

17.6

73.6

Equilibrium

1956BRO

22.5

94.1

18.0 16.3 10

75.3 68.2 42

(1) (2) (1) (1) (1)

113 130G4.6 79 54 17

(1) Review (2) Re-anal.

(1) 1989HAA (2) 2001FRO/FRE

F3B–N(CH3)3 –P(CH3)3 –O(CH3)2 –S(CH3)2

31.1G1.0 35.0G0.8 36.4G1.0 34.8G0.5 38.3

27 31.0G1.1 19 13 4

(2) 2001FRO/FRE

Cl3B–N(CH3)3

30.5

127.6

Re-anal.

2001FRO/FRE

B(CH3)3–PH(CH3)2 –P(CH3)3 BF3–PH(CH3)2

11.4 16.5 14.7

47.7 69.0 61.5

Equilibrium

1956BRO

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 23.1.1 (continued) BDEs of B–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

B–C

107G7

448G29

MS

1964VER/STA

B–Si

(1) 68 (2) 75.8G2.7

285 317G12

MS

(1) 1964VER/STA (2) 1996VIS/SCH

H3B–CO

24.6

102.9

Derived

2001FRO/FRE

H2B–CH3

4.1G6

17G25

Derived from DfH0 in ref.

1987HET/COL

F2B–CH3

(1) w113 (2) 95–100

w472 397–418

(1) Pyrolysis (2) Review

(1) 1965SKI (2) 1973LIT/SPA

F2B–C2H3 –C3H7 –CHCH2

101 96 111

423 402 464

Review

1973LIT/SPA

F3B–CH3CN –PhCHO –Me2O

12.0G0.8 15.5G1.0 17.6G0.8

50.2G3.3 64.9G4.2 73.6G3.3

Re-anal.

2001FRO/FRE

Cl2B–C6H5

w122

w510

Pyrolysis

1972JON/PRI

Cl3B–CH3CHCHCHO –CH3CHCHC (O)OCH3 –CH3C(CH3) CHCHO –CH3CHCHCN

24.4G0.3 19.9G0.4

102.1G1.3 83.3G1.7

Calorimetry

1982CHI/MUL

25.4G0.3

106.3G1.3

19.2G0.2

80.3G0.8

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BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

23.1.2.

1049

BC–X bonds

Table 23.1.2 BDEs of BD–X Bonds

The broken bonds (boldfaceZdissociated fragment) BC(B)x–B xZ0 1 2 3 4 5 6 7 8 9 10 11 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (2) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (3)

18G14 44.7 99G16 185G35 164G14 62G14 127G16 97G12 92G12 125G12 129G18 127G12 184G35 w117

kJ/mol

Methods (reference in parentheses)

References

75G59 187 414G67 774G146 686G59 259G59 531G67 406G50 385G50 523G50 540G75 531G50 770G146 w490

(1) CID (2) Derived

(1) 1988HAN/WHI (2) 1996SMI/YAT

(3) Extrapolate

(3) This volume

BC–Pt

75G23.4

314G98

Derived from IP in ref.

1996NIST

BC–Ar

7.8

32.7

MS

1978DIN/KAR

(1) 50.0 (2) 47.3G1.2

209 198G5

(1) Derived (2) Derived from IP in ref.

(1) 1973LIT/SPA (2) 1996NIST

(1) 99.2 (1) 14.5

415 61

(1) 116G4 (2) 109.9G2.4

485G17 460G10

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

BC(H)x–H xZ0

1 2

BC–F

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 23.1.2 (continued) BDEs of BC–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

BC–Cl

(1) 81.4G2.6 (2) 73.7G5

340.6G10.9 308G21

(1) MS (2) Derived from IP in ref.

(1) 1996HIL (2) 1996NIST

Cl2BC–Cl

19.69G0.05

82.40G0.19

PFI-PE

2005YAN/MO

BC–Br

39.3G5

164G21

Derived from IP in ref.

1996NIST

3.8G0.2, at 0 K 3.0G0.3

15.9G0.8

Equilibrium

1998KEM/BUS

14.7G0.5, at 0K 18.1G0.5

61.5G2.1

Equilibrium

1998KEM/BUS

(1) 72G12 (2) 78G11.5

301G50 326G48

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

O150 O138 O125.7 O125.7 O125.7 O125.7 O125.7 O125.7 w125 w125

O627 O579 O526 O526 O526 O526 O526 O526 w521 w521

CID

1991RUA/HIN

BC(H2)x–H2 xZ0 1

HBC(H2)x–H2 xZ0 1

BC–O

BC(B)x–O xZ1 2 3 4 5 6 7 8 9 10

References

12.6G1.3

75.7G2.1

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BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

11 12 13

1051

w120 w101 w120

w502 w425 w502

BC–Se

71G23.4

298G98

Derived from IP in ref.

1996NIST

BC–C

(1) 55G5 (2) 67.8G13.8

230G105 284G58

(1) 1974GUR/KAR (2) 1996NIST

BC–Si

(1) Derived (2) Derived from IP in ref.

(2) 87.2G3.6

365G15

(CH3)2BC–CH3

7.8G1

32.6G4.2

ICR

1976MUR/BEA

23.1.3 BK–X bonds Table 23.1.3 BDEs of BL–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

BK–B

(1) 97.7 (2) 93G10

408.9 388G42

(1) Derived (2) Derived from EA in ref.

(1) 1996SMI/YAT (2) 1996NIST

BHK 4 –BH3

41.2

172

Est. by exp.

1988WOR/SQU

BHK 4 –HOCH3 –HO-iso-C3H7

4.1 3.8

17.2 15.9

IR-NMR

1998EPS/SHU

BHK 4 –HOCHðCF3 Þ2 –HOCH2CF3 –indole

6.5 5.2 2.5

27.2 21.8 10.5

IR-NMR

1998EPS/SHU

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Comprehensive Handbook of Chemical Bond Energies

23.2 Al–, and AlG–X bonds 23.2.1 Al–X bonds Table 23.2.1 BDEs of Al–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment) Al(Al)x–Al xZ0 1

(1) (2) (3) (4)

Methods (reference in parentheses)

kcal/mol

kJ/mol

36.6 31.8G1.4 55.3 63.2G0.1

153 133G5.8 231.6 264.3G0.5

(1) (2) (3) (4)

Review Spectroscopy Spectroscopy PD

References (1) (2) (3) (4)

1979MIE/GIN 1990FU/LEM 1988FU/LEM 2001FU/RUS

Al(110, surf.)–Al Al(311, surf.)–Al Al(331, surf.)–Al

9.9 11.1 10.6

41.5 46.3 44.4

FIM

1994KEL(c)

Al(Al)x–Al xZ3 4 5 6 7 8 9 10 11 12 13 14 15 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

251 261 32.8 193 251 261 270 299 347 289 256 275 280 w293

(1) PD

(1) 1990JAR/RAY

(2) Extrapolate

(2) This volume

H3Al–AlH3

33G5

138G21

MS

2005GOE/HER

I3Al–AlI3

24.6

102.9

Derived from DfH0 in ref.

1996NIST

60.0 62.3 78.4 46.1 60.0 62.3 64.6 71.5 83.0 69.2 61.1 65.7 66.9 w70.1

7366—CHAPTER 23—3/2/2007—12:01—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1053

Al–Li

18.2

76.1

R2PI

1994BRO/PIL

Al–Ca

12.6

52.7

Spectrometry

1994BEH/MOR

Al–U

78G7

326G29

MS

1967GIN/BLU

Al–Ti

63.0

263.4

MS

1979HUB/HER

Al–V –Cr –Co

35.2G0.2 53.3G0.2 43.4G0.1

147.4G1.0 222.9G0.9 181.6G0.2

Spectrometry

2001FU/RUS

Al–Ni

53.7G1.2

224.7G4.8

Spectrometry

1993BEH/ARR

Al–Pd

60.8G2.9

254.4G12.1

MS

1976COC/GIN

AlNi(110, surf.)–Pt

11.1

46.3

FIM

2001NIL/COR

Al–Cu

54.3G0.3

227.1G1.2

Spectrometry

1993BEH/ARR(b)

Al–Ag

43.9G2.2

183.7G9.2

MS

1973CUT/FAB

Al–Au

(1) 77.7G3.1 (2) 77.9G1.5

325G13 325.9G6.3

MS

(1) 1973CUT/FAB (2) 1973GIN/BLU

Al–Ne

0.93

3.9

Spectroscopy

1998YAN/DAG

Al–Ar

(1) 1.40 (2) 1.24 (3) 1.36 (4) 1.24

5.87 5.18 5.69 5.18

Spectroscopy

(1) (2) (3) (4)

Al–Kr

(1) 1.45

6.05

Spectroscopy

(1) 1992HEI/FU

1990MCQ/GOL 1992HEI/FU 1993STA/SCH 1996STA/KNI

(continued)

7366—CHAPTER 23—3/2/2007—12:01—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1054

Comprehensive Handbook of Chemical Bond Energies

Table 23.2.1 (continued) BDEs of Al–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

Al–Xe

Al(H)x–H xZ0

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 1.45

6.05

(1) 1.78G0.16 (2) 1.77

7.43G0.69 7.39

Spectroscopy

(1) 1989CAL/MIT (2) 1998STA/KNI

(1) (2) (3) (4)

295.2G1.0 283.7G8 292.2G7.7 288G13

(1) (2) (3) (4)

(1) (2) (3) (4)

(5) 47.9G6 (5) 87.5G6

200G25 366G25

Spectroscopy MS Spectroscopy Derived from DfH0 in ref. (5) Derived from DfH0 in ref.

Al–D

69.4

290.4

Spectroscopy

2000URE/GOM

Al(surf.)–H

44

184

Review

1979ERT

Si(solid)Al–H

33.2G0.5

138.9G1.9

Kinetics

1989ZUN/WEB

Al(Cl)x–H xZ1 2

37.3G7 69.1G7

156G30 289G30

Derived from DfH0 in ref.

1996GUR/VEY

AlHCl–H AlFCl–H

80G7 67.8G10

335G30 284G42

Derived from DfH0 in ref.

1996GUR/VEY

1 2

70.5G0.2 67.8G2 69.8G1.8 68.9G3

(2) 1998STA/KNI

1979HUB/HER 1981KAN/MOO 1983NAR/RAJ 1996NIST

(5) 1996GUR/VEY

7366—CHAPTER 23—3/2/2007—12:01—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

H–AlO AlO–H

1055

60.1 111.1

251 465

Derived from DfH0 in ref.

1996NIST

(1) 159G3 (2) 161.3

665G12.6 675

(1) 1966MUR/HIL(b) (2) 1996NIST

121.5 142

508 594

(1) MS (2) Derived from DfH0 in ref.

Al(Cl)x–F xZ1 2

123.7G15 141G10

518G63 590G42

Derived from DfH0 in ref.

1996NIST

AlFCl–F

140.8G15

589G63

1996NIST

AlHCl–F

154.2G10

645G42

Derived from DfH0 in ref.

OAl–F Al(FO)–F

174.0 145

728 607

Derived from DfH0 in ref.

1996NIST

(1) 121.3G0.2 (2) 120

507.5G1.0 502

(1) 1979RAM/RAI (2) 1996NIST

(2) 83.7 (2) 101.7

350 426

(1) Spectroscopy (2) Derived from DfH0 in ref.

88.5G7 120.6G10

370G30 505G42

Derived from DfH0 in ref.

1996GUR/VEY

Al(F)x–F xZ0

1 2

Al(Cl)x–Cl xZ0

1 2

Al(H)x–Cl xZ1 2

1996GUR/VEY

(continued)

7366—CHAPTER 23—3/2/2007—12:01—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1056

Comprehensive Handbook of Chemical Bond Energies

Table 23.2.1 (continued) BDEs of Al–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

AlHCl–Cl

115.5G10

483G42

Derived from DfH0 in ref.

1996GUR/VEY

Al(F)x–Cl xZ1

82.1G15

344G63

1996NIST

101.8G15

426G63

Derived from DfH0 in ref.

AlFCl–Cl

101G15

423G63

Derived from DfH0 in ref.

1996NIST

AlHF–Cl

118.3G10

495G42

Al(OH)x–Cl xZ1

75.3G12

315G50

1996GUR/VEY

113G12

473G50

Derived from DfH0 in ref.

Al(OH)Cl–Cl

113G12

473G50

Derived from DfH0 in ref.

1996GUR/VEY

OAl–Cl

128.2

536

Derived from DfH0 in ref.

1996NIST

Al–Br

102.6G1.4

429.2G5.8

MS

1989HIL/LAU

Al–I

88.4G0.5

369.9G2.1

Spectroscopy

1978MAR/BAR

2

2

7366—CHAPTER 23—3/2/2007—12:01—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1057

Al(F)x–O xZ1 2

135 158.6

565 664

Derived from DfH0 in ref.

1996NIST

Al(Cl)–O

130.5

546

Derived from DfH0 in ref.

1996NIST

Al(Al)x–O xZ0

(1) 121.3G0.7 (2) 123.1G1.0 (3) 120.0G2.5 (4) 129.5

507.5G2.9 515G4 501.9G10.6 542

(1) (2) (3) (4)

(1) (2) (3) (4)

Al(O)–O

96.2

402

Derived from DfH0 in ref.

1996NIST

Al(111, surf.)–O

23–25 (phys.)

96–106

STM

1998TRO/BRU

Al–N

(1) 85G10 (2) %88G3.6

356G42 %368G15

MS

(1) 1974GUR/KAR (2) 2000MEL/GIN

Al–P

51.8G3

216.7G12.6

MS

1966MAR/GIN

Al–As

48.4G1.7

202.7G7.1

MS

1979PIA

Al–Sb

51.7G1.4

216.3G6

MS

1978PIA/BAL

(1) 79.3G2.3 (2) 88

332G10 368

(1) 1995NAK/TAG (2) 1996GUR/VEY

(2) 63.8

267

(1) PES (2) Derived from DfH0 in ref.

1

Al(S)x–S xZ0

1

Mol. beam CID Spectroscopy Derived from DfH0 in ref.

1987COS/NAU 1992CLE/WEB 1999RED/AHA 1996NIST

(continued)

7366—CHAPTER 23—3/2/2007—12:01—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1058

Comprehensive Handbook of Chemical Bond Energies

Table 23.2.1 (continued) BDEs of Al–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment) Al–Se –Te

kcal/mol (1) (2) (1) (2)

80.7G2.4 76G3 64.0G2.4 64G3

kJ/mol

Methods (reference in parentheses)

References

337.6G10 318G13 267.8G10 268G13

(1) MS (2) Review

(1) 1971UY/DRO (2) 1974GUR/KAR

Al–C

64

267.7

Spectroscopy

2001TZE/MAV

Al–Si

59G3

246.9G12.6

MS

1975CHA/ALL

Al(crystal)–H2

27G1

113G4

TPD

1991WIN/RES

F3Al–LiF –NaF –KF –RbF –CsF

70.7 81.5 85.8 86.1 84.4

295.9 341.2 359 360.2 353.3

Derived

1985ZHU/NIK

Al(polycr. surf.)–O2

152–211

635–882

Calorimetry

1960BRE/HAY

Al(OH)x–OH xZ0

(1) 130.7G3

547G13

(1) 1996NIST

(2) 84.1G6 (2) 129.6G6

352G25 542G25

Derived from DfH0 in ref.

Al(F)(OH)–OH

127.3G7

533G30

Derived from DfH0 in ref.

1996GUR/VEY

Al(F)x–OH xZ1 2

82.6G7 115.7G12

346G30 484G50

Derived from DfH0 in ref.

1996GUR/VEY

1 2

(2) 1996GUR/VEY

7366—CHAPTER 23—3/2/2007—12:01—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1059

Al(Cl)(OH)–OH

124.9G7

523G30

Derived from DfH0 in ref.

1996GUR/VEY

Al(Cl)x–OH xZ1 2

85.9G7 115.2G12

359G30 482G50

Derived from DfH0 in ref.

1996GUR/VEY

Al–OAl

129.5

542

Derived from DfH0 in ref.

1996NIST

(AlO)–AlO

135G5

565G21

Review

1967DRO/GOL

g-Al2O3(surf.)–CO

w9.6

w40

Calorimetry

1998BOL/CER

Al(polycs. surf.)–CO

4.2

17.6

Review

1964HAY/TRA

Al(111, surf.)–CO

4.8

20.3

Photoemission

1980CHI/KAI

Al2O3–CO Al2O3/CaO–CO Al2O3/BaO–CO

13–19 w7 w11

55–80 w30 w45

Calorimetry

1999BOL/MAG

Al–CO2

O9

O38

Fluorescence detection

1988PAR/MIT(b)

Al–NC –CN

116.6 111.2

487.9 465.3

Derived from DfH0 in ref.

1999MEL/GIN

Al2O3/NiAl(111, surf.)–H2O

10.7

44.8

TPD

2006OZE/PED (continued)

7366—CHAPTER 23—3/2/2007—12:01—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1060

Comprehensive Handbook of Chemical Bond Energies

Table 23.2.1 (continued) BDEs of Al–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Al–C2H2 –C2H4 –1-butene –trans-butene –tetramethylethylene –1,4-cyclohexadiene –benzene –toluene –o-xylene

O13 O16 O15 14.2G1 13.5G1

O54 O67 O63 59.4G4.2 56.5G4.2

O14 11.7G1 14.1G1 14.3G1

O59 49.0G4.2 59.0G4.2 59.8G4.2

h-Al2O3(surf.)–C6H6

2.8

Al2O3(0001, surf.) –C6H5I

Methods (reference in parentheses)

References

TR RF

1988MIT/SIM

11.6

NMR

1989BOD/BEE

11.3G0.5

47.3G2.1

Photochemical

1998SLO/SUN

Al–dimethyl ether –diethyl ether –tetrahydrofuran

9.2G0.6 9.2G1.2 10.8

38.5G2.5 38.5G5.0 45.2

TR RF

1988PAR/MIT

Al(100, surf.)–C(in TIBA) TIBAZAl(iC4H9)3

13

54

IR

1992ZEG/DUB

(CH3)3Al–ether

17.0

71.1

Calorimetry

1988PAR/MIT

(CH3)3Al–dimethyl ether –diethyl ether –tetrahydro -furan

21.9

91.6

Calorimetry

1968HEN/DUF

20.2 22.9

84.5 95.8

7366—CHAPTER 23—3/2/2007—12:02—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1061

Al2O3(111, surf.)–NO2

9.1

38

ESR

1995SCH/BEC

Al2O3/NiAl(111, surf.)–NO2

8.7

36.6

TPD

2006OZE/PED

Al–NH3

(1) 12.2 (2) 10.4

51.1 43.4

Derived

(1) 1998PAL/LAT (2) 1998PAL/SAT

–2NH3

(1) 18.2

76.2

(1) 32.8G1.4 (2) 41

137.1G5.9 172

(1) MS (2) Review

(1) 1999TIM/SUV (2) 2001SCH

(3) 47.5G2.0

198.7G8.4

(3) Derived

(3) 1989HAA

(1) 34.4G1.1 (2) 41.0

143.8G4.6 171.5

(1) MS (2) Review

(1) 1999TIM/SUV (2) 2001SCH

(2) 44.8

187.4

(1) 27.6G0.3 (2) 26.8 (1) 30.0G0.2 (3) 31

115.5G1.3 112.1 125.5G0.8 130

(1) Review (2) Combined (3) Review

(1) 2001SCH (2) 2006WAN/CRE (3) 1989HAA

(1) 26.5G0.2

110.9G0.8

(1) 23

96

Review

(1) 1989HAA

(2) 22.1G0.2

92.5G0.8

Br3Al–PBu3

47.5

198.7

–PPh3

34.9

146.0

(CH3)3Al–PPh3

17.6G0.2

73.6G0.8

(CH3)3Al–O(CH3)2

22

92

Cl3Al–NH3 –N(CH3)3

Br3Al–NH3 –N(C2H5)3

(CH3)3Al–NH3 –N(CH3)3 –N(C2H5)3

(CH3)3Al–P(CH3)3

(2) 2001SCH

Review

2001SCH

Review

2001SCH

(continued)

7366—CHAPTER 23—3/2/2007—12:02—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1062

Comprehensive Handbook of Chemical Bond Energies

Table 23.2.1 (continued) BDEs of Al–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment) –S(CH3)2 –Se(CH3)2

I3Al–pyridine

kcal/mol

kJ/mol

18 16

75 67

37.3G1.7

156G7

Methods (reference in parentheses)

MS

References

2002TIM/SUV

23.2.2 AlC– and AlK–X bonds Table 23.2.2 BDEs of AlD– and AlL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment) AlC(Al)x–Al xZ0 1 2 3

4

5

6 7 8 9

kcal/mol (1) (2) (1) (2) (1) (2) (1) (2) (3) (1) (2) (3) (1) (2) (3) (2) (3) (2) (3) (2) (3) (2) (3)

20.8G6.9 28.8G8.3 25.8G8.1 30.7G5.3 46.8G6.9 48.2G8.5 59.3G8.1 55.9G6.0 50.7G3.5 55.3G6.9 59.7G8.1 54.2G3.5 103.1G9.2 84.2G14.3 81.9G5.8 21.7G6.0 43.8G4.6 36.4G14.3 60.0G6.9 39.9G9.2 64.5G8.1 35.1G9.2 66.9G8.1

kJ/mol 87G29 121G35 108G34 128G22 196G29 202G36 248G34 233G25 212G14 232G29 250G34 227G14 431G39 352G60 343G24 91G25 183G19 152G60 251G29 167G39 270G34 147G39 280G34

Methods (reference in parentheses)

References

(1) CID (2) CID

(1) 1987HAN/RUA (2) 1999ING/TAK

(3) PD

(3) 1990JAR/RAY

7366—CHAPTER 23—3/2/2007—12:02—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

10 11 12 13 14 15 N

AlC–(Al)xAl xZ1 2 3 4 5 6 7 8 9

(3) (3) (3) (3) (3) (3) (4)

71.7G8.1 81.3G9.2 71.7G11.5 59.8G13.8 66.9G13.8 69.3G13.8 w70.1

300G34 340G39 300G48 250G58 280G58 290G58 w293

(1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (2) (2) (2) (2)

30.0G8.1 31.4G4.2 19.6G9.2 21.2G7.4 30G8.1 37.6G7.4 35.7G6.9 38.0G5.1 58.8G16.1 42.7G7.6 29.3G8.1 29.7G8.1 30.7G8.1 33.0G9.2

1063

(4) Extrapolate

(4) This volume

125G34 131G17 82G39 89G31 125G34 157G31 150G29 159G21 246G68 178G32 123G34 124G34 128G34 138G39

CID

(1) 1987HAN/RUA (2) 1999ING/HAR

AlC 2 –Alx xZ2 3 4

58.8G8.1 77.3G15.0 113.0G12.7

246G34 323G63 473G53

CID

1987HAN/RUA

AlC 3 –Alx xZ2 3

99.2G10.4 130.8G12.7

415G43 547G53

CID

1987HAN/RUA

AlC x –Al2 xZ4 5

122.2G8.1 167.2G9.2

511G34 700G39

CID

1987HAN/RUA

AlC–Ca

35.5

148.5

Spectrometry

1994BEH/MOR (continued)

7366—CHAPTER 23—3/2/2007—12:02—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1064

Comprehensive Handbook of Chemical Bond Energies

Table 23.2.2 (continued) BDEs of AlC– and AlK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

AlC–Ag –Au

2G11.7 11.1G7

9G49 46.8G30

Derived from IP in ref.

1996NIST

AlC–Ar –Kr

3.70 1.32

15.47 5.54

Spectrometry

1992HEI/FU

AlC–H

38.5

161.1

Derived from DfH0 in ref.

1988LIA/BAR

AlC–F

(1) 80G10 (2) 75G5

335G42 314G21

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

(1) 30G10 (2) 41G10

126G42 173G42

AlC–Br –I

26.1G2.4 12G6.9

109G10 50G29

Derived from IP in ref.

1996NIST

AlC–O

(1) (2) (3) (4)

165G15 171.5G4 145G12 166.7G12.0

(1) Thermochem. (2) Ion reactions (3) GIB MS (4) Derived from IP in ref.

(1) (2) (3) (4)

AlC–S

(1) K1.7G2.9

K7G12

(1) Derived from IP in ref

(1) 1996NIST

(1) 27.3G11.8 (2) 25G15 (1) K5.5G11.8

114G49 105G63 K23G49

(2) Derived

(2) 1974GUR/KAR

–Cl

–Se –Te

39.4G3.7 41.0G0.9 34.6G2.8 39.8G2.9

7366—CHAPTER 23—3/2/2007—12:02—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1975STA/BEA 1982HAL/BEA 1986WEB/ELK 1996NIST

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1065

AlC–P

K3.9G9.8

K16G41

Derived from IP in ref.

1996NIST

AlC–Si

47G23.3

197G97

Derived from IP in ref.

1996NIST

AlC(H2)x–H2 xZ0 1

1.35G0.15 1.10G0.15

5.6G0.6 4.6G0.6

Equilibrium

1998KEM/BUS(b)

AlC–N2

1.3

5.6

PI

1995BRO/DUN(b)

AlC–HCN

28G6

117G25

FT ICR

1995STO/HOL

AlC–CO2

R7.0

R29.3

PI

1995BRO/DUN(b)

AlC(H2O)x–H2O xZ0 1 2 3 N

(1) (1) (1) (1) (2)

104G15 67G5 64G8 52G6 w44

(1) CID

(1) 1994DAL/TJE

(2) Extrapolate

(2) This volume

AlC–NH3 –2NH3

AlC(CH4)x–CH4 xZ0 1 2 3 4 5 N

24.9G3.6 16.1G1.2 15.2G1.8 12.5G1.4 w10.5

(1) 39.0 (2) 31.8 (1) 62.5

163.1 133.1 261.5

Derived

(1) 1998PAL/LAT (2) 1998PAL/SAT

(1) (2) (2) (2) (2) (2) (2) (3)

25G8 25.3G1.3 20.1G1.3 16.9G1.3 13.4G2.5 12.6G2.1 w11.7 w8

(1) FT-ICR (2) HP MS

(1) 1996STO/SCH (2) 1998KEM/BUS(b)

(3) Extrapolate

(3) This volume

6G2 6.05G0.3 4.80G0.3 4.04G0.3 3.2G0.6 3.0G0.5 w2.8 w2

(continued)

7366—CHAPTER 23—3/2/2007—12:02—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1066

Comprehensive Handbook of Chemical Bond Energies

Table 23.2.2 (continued) BDEs of AlC– and AlK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment) AlC(C2H2)x–C2H2 xZ0 1

AlC(C2H4)x–C2H4 xZ0

1

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 13G2 (2) 14.0G1.0 (2) 13.6G1.5

54G8 58.6G4.2 56.9G6.3

(1) FT-ICR (2) HP MS

(1) 1996STO/SCH (2) 1998KEM/BUS(b)

(1) (2) (3) (2)

54G8 62.3G3.3 35.7G14.5 w38

(1) FT-ICR (2) HP MS (3) PD

(1) 1996STO/SCH (2) 1998KEM/BUS(b) (3) 1999CHE/WON

13G2 14.9G0.8 8.5G3.5 w9

AlC–C2H6

(1) 9G2 (2) 9.3G0.5

38G8 38.9G2.1

(1) FT-ICR (2) HP MS

(1) 1996STO/SCH (2) 1998KEM/BUS(b)

AlC–CH3F –HC(O)H

21.5G2.0 27.5G2.5

90.0G8.4 115.1G10.5

HP MS

1997BOU/BRE

AlC–MeOH –EtOH

33.4 36.6

139.7 153.1

Derived

1997BOU/BRE

AlC(L)x–L, LZMeCN xZ0 1

36.3 22.2

151.9 92.9

HP MS

1997BOU/BRE

AlC(L)x–L, LZMeOMe xZ0 1

37.9 22.6

158.6 94.6

HP MS

1997BOU/BRE

7366—CHAPTER 23—3/2/2007—12:02—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1067

AlC(L)x–L, LZMeCOMe xZ0 1

42.3 28.3

177.0 118.4

Derived

1997BOU/BRE

AlC–EtC(O)Et

45.7

191.2

Derived

1997BOU/BRE

AlC(L)–L LZacetone-d6 cyclopentanone diethylether tetrahydrofuran tetrahydropyran

28.2 28.7 30.8 31.0 30.6

118.0 120.1 128.9 129.7 128.0

HP MS

1997BOU/BRE

(1) 39 (2) 35.2G2 (1) 41.3

163 147.3G8.4 173

(1) FT-ICR (2) Kinetics

(1) 1995STO/HRU (2) 1996DUN/KLI

AlC–pyridine –pyrimidine

45.8G2.5 38.3G1.5

191.5G10.3 160.1G6.1

CID

2002ROD/STA 2001AMU/ROD

AlC–phenol –indole

37G4 45G4

154.8G16.7 188.3G16.7

Combined

1999RYZ/DUN

AlC(L)x–L, LZpyrrole xZ0 43.9 1 !25.2

183.7 !105.4

Kinetics

2000GAP/YAN

AlC–imidazole

55.5G2

232.4G8.2

CID

2004RAN/AMU

AlK–Al

55.5G2.0

232G8.4

Derived from EA in ref.

1996NIST

AlC–C6H6 –C6D6

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Comprehensive Handbook of Chemical Bond Energies

23.3 Ga–, GaC–, and GaK–X bonds 23.3.1 Ga–X bonds Table 23.3.1 BDEs of Ga–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

References

28G4 26.4G1.7 28.1 27.4G1.1 !25.4

117G17 110.3G7 117.6 114.5G4.8 !106.4

(1) Review (2) MS (3) Review (4) MS (5) Spectrometry

(1) (2) (3) (4) (5)

Ga–Ga

(1) (2) (3) (4) (5)

Ga(surf.)–Ga

40.6

169.8

Mol. beam

1994YAN/YAM

GaN(1000, surf.)–Ga

18.9

79.1

RHEED

2006HE/MOO

FGa–GaF F2Ga–GaF2 F3Ga–GaF3

33.7G12 68.7G12 41.8G12

141G50 287G50 175G50

Derived from DfH0 in ref.

1996GUR/VEY

ClGa–GaCl Cl2Ga–GaCl2 Cl3Ga–GaCl3

19.6G5 38.4G12 23.2G5

82G21 161G50 97G21

Derived from DfH0 in ref.

1996GUR/VEY

BrGa–GaBr Br2Ga–GaBr2 Br3Ga–GaBr3

24.1G7 28.1G12 21G5

101G30 118G50 88G21

Derived from DfH0 in ref.

1996GUR/VEY

IGa–GaI I2Ga–GaI2 I3Ga–GaI3

18.2G12 24.3G12 20.4G12

76G50 102G50 85G50

Derived from DfH0 in ref.

1996GUR/VEY

7366—CHAPTER 23—3/2/2007—12:02—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1970DAR 1991SHI/MAN 1996SMI/YAT 1998BAL/GIG 2003TAO/DAG

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

GaN(0001, surf.)–Ga

50.7G4.6

1069

212.3G19.3

Mol. beam

1996GUH/BOJ

(As)Ga(110, surf.)–GaR3 RZMe 46.6 Et 37.8 nPr 36.8 i-Pr 35.6 n-Bu 36.1 t-Bu 33.7

195 158 154 149 151 141

Desorption

1998WON/MCB

Ga–In

22.5G0.7

94.0G3

MS

1998BAL/GIG

GaAs(100, surf.)–In

53.5G1.2

223.8G4.8

XPS

1989MCC/DON

GaAs(110, surf.)–He

0.10, at 0 K

0.41

Scattering

1987DOA/NGU

Ga–Ar –Kr –Xe

0.95 0.97 1.26

3.96 4.08 5.27

Spectroscopy

1998STA/KNI

Ga–Li

31.8G3.5

133.1G14.6

MS

1975GUG/NEU

GaAs(crystal)–Li

27.7G0.7

115.8G2.9

Diffusion

1997LEO/GIS

Ga–Cu

51.6G3.6

215.9G15

MS

1972CAR/BER

Ga–Ag

(1) 43.0G3.6 (2) 37G4

180G15 154.8G16.7

(1) MS (2) Review

(1) 1972CAR/BER (2) 1974GUR/KAR

Ga–Au

69.3G3.6

290G15

MS

1972CAR/BER

Ga–H

(1) !65.5

!274

(1) Spectroscopy

(1) 1971KRO/LAG (continued)

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1070

Comprehensive Handbook of Chemical Bond Energies

Table 23.3.1 (continued) BDEs of Ga–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 62.7G2 (3) 71.3 (4) 65.9

262.2G8 298.1 276

(2) MS (3) Spectroscopy (4) Derived from DfH0 in ref.

(2) 1981KAN/MOO (3) 1982RAJ/PRA (4) 1996GUR/VEY

Ga–D

!66.1

!276.5

Spectroscopy

1971KRO/LAG

Ga(polycs. surf.)–H

40

167

Electrochemical

1970KRI

Ge(O)–H

121.5

508

Derived from DfH0 in ref.

1996GUR/VEY

Si(solid)Ga–H

32.3G0.7

135.1G2.9

Kinetics

1989ZUN/WEB

(1) 138G3.5 (2) 139.6G3

577.4G14.6 584G13

(1) 1966MUR/HIL(b) (2) 1996GUR/VEY

(2) 86.9G12 (2) 115.7G12

364G50 484G50

(1) MS (2) Derived from DfH0 in ref.

(1) 110.7G0.7 (2) 110.6G3

463.1G2.9 463G13

(1) 1993GLO/GNA (2) 1996GUR/VEY

(2) 65.2G12 (2) 79.6G12

273G50 333G50

(1) Photolysis (2) Derived from DfH0 in ref.

96G3

402G13

1996GUR/VEY

48G12 61.1G12

201G50 256G50

Derived from DfH0 in ref.

Ga(F)x–F xZ0

1 2

Ga(Cl)x–Cl xZ0

1 2

Ga(Br)x–Br xZ0 1 2

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BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

Ga(I)x–I xZ0

(1) 81G2.3 (2) 79.8G3

339G9.6 334G13

(2) 43.1G12 (2) 46.3G12

180G50 194G50

Ga–O

(1) 83.5G10 (2) 89.5G5

Ga–Te

1071

(1) Review (2) Derived from DfH0 in ref.

(1) 1968GAY (2) 1996GUR/VEY

349G42 374G21

(1) Review (2) Derived from DfH0 in ref.

(1) 1983PED/MAR (2) 1996GUR/VEY

(1) 60G6 (2) 63G5

251G25 264G21

(1) MS (2) Review

(1) 1968UY/MUE (2) 1974GUR/KAR

Ga–P

54.9G3

229.7G12.6

MS

1971GIN/PIA

Ga–As

48.4G1.2

202.5G4.8

Spectroscopy

1990LEM/BIS

GaAs(surf.)–As

60

251

Mol. beam

1968ART

Ga–Sb

45.9G3

192.0G12.6

MS

1974PIA/BAL

GaAs(110, surf.)–Sb

10.4 (phys.)

43.4

PED

1997ASC/AVI

GaAs(110, surf.)–Sb

57.7

241

AES

1980NAG/MIY

Ga–Bi

37.9G4

158.6G16.7

MS

1972PIA/DES

GaAs(100, surf.) –GaSb

19.6 (phys.)

82.0

MBE

1999WAN/FOR

GaAs(100, surf.) –GaSb

49.6

207.4

MBE

1999WAN/FOR

1 2

(continued)

7366—CHAPTER 23—3/2/2007—12:03—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1072

Comprehensive Handbook of Chemical Bond Energies

Table 23.3.1 (continued) BDEs of Ga–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

GaAs(110, surf.)–H2

13.8

57.7

TPD

1984MOK/KOH

Ga–N2

(1) 3.6 (2) 4.5

15.2 19

(1) LIF (2) Raman /UV/Vis

(1) 1999GRE/HAN (2) 2005HIM/HEB

Ga–OH

108.2

453

1996GUR/VEY

Ga–OGa

123.9G5

518G21

Derived from DfH0 in ref.

Ga–N2

O3.6

O15.2

LIF

1999GRE/HAN

F3Ga–LiF –NaF –KF –RbF –CsF

65.4 75.4 75.7 75.7 75.7

273.6 315.5 316.7 316.7 316.7

Derived

1985ZHU/NIK

GaAs(110, surf.)–NO2 6G2

25G8

Mol. beam

1993FEL/BAH

GaAs(110, surf.)–NO2 9G2

38G8

Mol. beam

1995BAH/FEL

GaAs(110, surf.)–As4 GaAs(110, surf.)–As4

w5.5 (phys.) w8.8

w23 w37

Mol. beam

1975FOX/JOY

Ga–NH3

7.4

30.9

Derived

1998PAL/SAT

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BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1073

Cl3Ga–NH3 Br3Ga–NH3

32.1G0.6 32.8G0.2

134.2G2.5 137.1G0.8

MS

1999TIM/SUV

(CH3)3Ga–NH3

(1) 15.2G1.5 (2) 16.3G0.5 (3) 18.4

63.6G6.3 68.2G2.1 77

(1) Equilibrium (2) Equilibrium (3) Combined

(1) 2001PEL/CAR (2) 2005CRE/WAN (3) 2006WAN/CRE

(CH3)2Ga–CH3

64.6

270.3

MS

1991CHE/DAP

Ga–C2H2 –1-C4H8 –Ga(CH3)3

9G2 9G2 14G2

37.7G8.4 37.7G8.4 58.6G8.4

RF

1986MIT/HAC

(C2H5)2O–GaCl3 –GaBr3 –GaI3

50.7 47.4 33.4

212.1 198.3 139.7

Derived

1966GRE/SRI

(CH3)3Ga–O(C2H5)2

12.1G0.2

50.6G0.8

Calorimetry

1976BAE/GAI

(CH3)2S–GaCl3 –GaBr3 –GaI3

54.2 50.6 40.2

226.8 211.7 168.2

Derived

1966GRE/SRI

(C2H5)2S–GaCl3 –GaBr3 –GaI3

56.2 51.8 40.8

235.1 216.7 170.7

Derived

1966GRE/SRI

I3Ga–pyridine

33.5G1.7

140G7

MS

1995TIM/GRI

7366—CHAPTER 23—3/2/2007—12:03—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1074

Comprehensive Handbook of Chemical Bond Energies

23.3.2 GaC–X bonds Table 23.3.2 BDEs of GaD –X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

GaC–Ga

30.2

126.3

Derived

1996SMI/YAT

GaC–F

(1) 31G10 (2) 32.6G3.6

130G42 136G15

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

GaC–Cl –Br –I

20.5G5 13.5G3.8 9.9G3.6

86G21 56.5G16 41.6G15

Derived from IP in ref.

1996NIST

GaC–O

(1) 12 (2) 11G12

50 46G50

Derived

(1) 1974GUR/KAR (2) 2004LAV/BLA

GaC–Te

4.6G5

19G29

Derived from IP in ref.

1996NIST

GaC–Sb –Bi

9G23 15G23.4

38G96 62G98

Derived from IP in ref.

1996NIST

GaC–NH3

29.3

122.5

Derived

1998PAL/SAT

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BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1075

23.3.3 GaK–X bonds Table 23.3.3 BDEs of GaL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

GaK–Ga

49.3

206.3

Derived

1996SMI/YAT

GaHK 4 –HOCH3 –HO-iso-C3H7

4.3 4

18.0 16.7

IR-NMR

2004BEL/FIL

GaHK 4 –HOCH2 CH2 F –HOCH2CF3

4.4 5.4

18.4 22.6

IR-NMR

2004BEL/FIL

GaHK 4 –indole –HN2C6H4-p-NO2

4.4 2.6

18.4 10.9

IR-NMR

2004BEL/FIL

23.4 In– and InG–X bonds 23.4.1 In–X bonds Table 23.4.1 BDEs of In–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

In–In

(1) 24.2 (2) 24.9 (3) 21G2 (4) 20.1 (5) 19.6G1.4

101.2 104 88G8 84.1 82.0G5.7

(1) (2) (3) (4) (5)

MS Review Raman Review MS

FIn–InF

34.8G12

146G50

Derived from DfH0 in ref.

References (1) (2) (3) (4) (5)

1979HUB/BER 1979MIE/GIN 1983FRO/SCH 1996SMI/YAT 1998BAL/GIG

1996GUR/VEY (continued)

7366—CHAPTER 23—3/2/2007—12:03—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

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Comprehensive Handbook of Chemical Bond Energies

Table 23.4.1 (continued) BDEs of In–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

F2In–InF2 F3In–InF3

88.5G12 55.9G12

370G50 234G50

ClIn–InCl

21G3

88G13

Cl2In–InCl2 Cl3In–InCl3

42.1G12 34.2G6

176G50 143G25

BrIn–InBr

21.1G6

88G25

Br2In–InBr2 Br3In–InBr3

56.2G12 27.9G6

235G50 117G25

IIn–InI

19.3G7

81G30

I2In–InI2 I3In–InI3

28.9G12 26G6

121G50 109G25

In–Ga

22.5G0.7

In–Ar

(1) (2) (1) (2) (1) (2)

–Kr –Xe

2.08 1.00 3.23 1.16 5.00 1.55

Methods (reference in parentheses)

References

Derived from DfH0 in ref.

1996GUR/VEY

Derived from DfH0 in ref.

1996GUR/VEY

Derived from DfH0 in ref.

1996GUR/VEY

94.0G3

MS

1998BAL/GIG

8.7 4.18 13.5 4.85 20.91 6.48

Spectroscopy

(1) 1989CAL/MIT (2) 1998STA/KNI

In–Li

22.1G3.5

92.5G14.6

MS

1975GUG/NEU

In–Cu

44.8G1.9

187.4G7.9

MS

1989BAL/DI

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BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1077

In–Ag

(1) 41G4 (2) 39.8G1.2

171.5G16.7 166.5G4.9

(1) Review (2) MS

(1) 1974GUR/KAR (2) 1989BAL/DI

In–Au

68.4G1.4

286.0G5.7

MS

1989BAL/DI

In–Zn

7.7

32.2

MS

1967DRO/GOL

In–Cd

32

134

Review

1974GUR/KAR

In–H

(1) 57G5 (2) 58.1 (3) 58.1 (4) 58.8G1

238G21 243.1 243.1 246G4

(1) (2) (3) (4)

(1) (2) (3) (4)

(5) 58.8

246.0

Review Spectroscopy Spectroscopy Derived from DfH0 in ref. (5) Review

In–D

58.8

246.0

Spectroscopy

1979HUB/HEB

In(H)x–H xZ1 2

34.1 70.7

142.7 295.8

Review

2006SKU/NIE

In(H)xCl–H xZ0 1

19.0 68.5

79.5 286.6

Review

2006SKU/NIE

InCl2–H

67.3

281.6

Review

2006SKU/NIE

In(polycs. surf.)–H

31

130

Electrochemical

1970KRI

(OIn)–H

116.7G5

488G21

Derived from DfH0 in ref.

1996GUR/VEY

1970DAR 1979HUB/HEB 1995WHI/DUL 1996GUR/VEY

(5) 2006SKU/NIE

(continued)

7366—CHAPTER 23—3/2/2007—12:03—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1078

Comprehensive Handbook of Chemical Bond Energies

Table 23.4.1 (continued) BDEs of In–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Si(solid)In–H

32.7G0.7

137.0G2.9

Kinetics

1989ZUN/WEB

(InP)Mg–H

32.3G1.8

135.1G7.7

SIMS

1993BAL/KUM

In(H)x(CH3)–H xZ0 1

33.7 70.8

141.0 296.2

Review

2006SKU/NIE

In(CH3)2–H

70.7

295.8

Review

2006SKU/NIE

In(H)x(C2H5)–H xZ0 1

34.7 70.1

145.2 293.3

Review

2006SKU/NIE

In(C2H5)2–H

69.6

291.2

Review

2006SKU/NIE

InCl(C2H5)–H

75.2

314.6

Review

2006SKU/NIE

In(H)x(OH)–H xZ0 1

21.8 68.8

91.2 287.9

Review

2006SKU/NIE

In(OH)2–H

68.3

285.8

Review

2006SKU/NIE

In(H)x(OCH3)–H xZ0 1

20.2 68.6

84.5 287.0

Review

2006SKU/NIE

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BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

InCl(OCH3)–H

1079

66.5

278.2

Review

2006SKU/NIE

(1) 121G3.5 (2) 123.3G3

506.3G14.6 516G13

(1) 1966MUR/HIL(b) (2) 1996GUR/VEY

(2) 82.1G12 (2) 116G12

344G50 485G50

(1) MS (2) Derived from DfH0 in ref.

(1) 104.3G2

436G8

(1) 1996GUR/VEY

(2) 102.3 (1) 60G12 (2) 43.5 (1) 69.2G12 (2) 87.2

428.0 251G50 182.0 290G50 364.8

(1) Derived from DfH0 in ref.

In(H)x–Cl xZ1 2

62.5 96.9

261.5 405.4

Review

2006SKU/NIE

In(H)(Cl)–Cl

91.8

384.1

Review

2006SKU/NIE

In(CH3)x–Cl xZ1 2

65.0 100.8

272.0 421.7

Review

2006SKU/NIE

In(CH3)(Cl)–Cl

92.6

387.4

Review

2006SKU/NIE

In(H)(C2H5)–Cl

98.7

413.0

Review

2006SKU/NIE

In(C2H5)2–Cl

100.3

419.7

Review

2006SKU/NIE

In(F)x–F xZ0

1 2

In(Cl)x–Cl xZ0

1 2

(2) 2006SKU/NIE

(continued)

7366—CHAPTER 23—3/2/2007—12:03—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

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Comprehensive Handbook of Chemical Bond Energies

Table 23.4.1 (continued) BDEs of In–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

In(OH)(Cl)x–Cl xZ0 1

47.5 88.8

198.7 371.5

Review

2006SKU/NIE

In(OH)2–Cl

88.8

371.5

Review

2006SKU/NIE

In(OH)(CH3)–Cl

95.7

400.4

Review

2006SKU/NIE

In(OCH3)(Cl)x–Cl xZ0 1

45.7 88.1

191.2 368.6

Review

2006SKU/NIE

InH(OCH3)–Cl

92.0

384.9

Review

2006SKU/NIE

In(Br)x–Br xZ0 1 2

97.7G2.4 49.6G12 52.2G12

409G10 208G50 218G50

Derived from DfH0 in ref.

1996GUR/VEY

(1) 78.6 (2) 77.3G2

329 323G8

(1) 1988VEM/JON (2) 1996GUR/VEY

(3) 73.3G0.3 (2) 41.2G12 (2) 41.3G12

306.9G1.1 172G50 173G50

(1) Spectroscopy (2) Derived from DfH0 in ref. (3) Spectroscopy

(1) !75.6G10 (2) 82.8G7

!316G42 346G30

(1) 1983PED/MAR (2) 1996GUR/VEY

(2) 101.3G7

424G30

(1) Review (2) Derived from DfH0 in ref.

In(I)x–I xZ0

1 2

In–O(In)x xZ0

1

(3) 1999KIN/HER

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BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1081

In–OH

96.7G4

405G17

Derived from DfH0 in ref.

1996GUR/VEY

In–S –Se –Te

68.8G3.5 58.6G3.5 51.5G3.5

287.9G14.6 245.2G14.6 215.5G14.6

MS

1968COL/DRO

In–P

47.3G2.0

197.9G8.4

MS

1976PIA/BAL

In–As

48.0G2.4

201G10

MS

1982PIA/GIG

In(Sb)x–Sb xZ0 1

36.3G2.5 66.7

151.9G10.5 279.1

MS

1959MAR/DRO

In–Bi

36.7G0.4

153.6G1.7

MS

1981RIE/HAR

In–NH3

8.3

34.7

Derived

1998PAL/SAT

Cl3In–NH3 Br3In–NH3

26.8G1.3 27.3G1.5

112.1G5.4 114.1G6.3

MS

1999TIM/SUV

(CH3)3In–NH3

15.0G0.6

62.8G2.5

Equilibrium

2005CRE/WAN

(1) 51.7 (2) 52.5 (1) 24.5 (2) 27.1 (1) 64.2 (2) 64.3

216.3 219.7 102.4 113.4 268.6 269.0

Review

(1) 1999BAU (2) 2006SKU/NIE

27.4 64.1

114.6 268.2

Review

2006SKU/NIE

In(CH3)x–CH3 xZ0 1 2

In(H)x–CH3 xZ1 2

(continued)

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1082

Comprehensive Handbook of Chemical Bond Energies

Table 23.4.1 (continued) BDEs of In–X Bonds

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

In(H)(CH3)–CH3

64.1

268.2

Review

2006SKU/NIE

In(Cl)x–CH3 xZ1 2

15.2 64.3

63.6 269.0

Review

2006SKU/NIE

In(Cl)(CH3)–CH3

62.9

263.2

Review

2006SKU/NIE

In(OH)x–CH3 xZ1 2

16.9 63.7

70.7 266.5

Review

2006SKU/NIE

In(OH)(CH3)–CH3

62.8

262.8

Review

2006SKU/NIE

In(OH)(Cl)–CH3

65.1

272.4

Review

2006SKU/NIE

In(H)x–C2H5 xZ1 2

23.1 59.1

96.7 247.3

Review

2006SKU/NIE

In(H)(C2H5)–C2H5

64.7

270.7

Review

2006SKU/NIE

In(C2H5)x–C2H5 xZ0 1 2

47.2 23.7 58.2

197.5 99.2 243.5

Review

2006SKU/NIE

In(H)(Cl)(C2H5)–C2H5 59.3

248.1

Review

2006SKU/NIE

In(Cl)2(C2H5)–C2H5

60.1

251.5

Review

2006SKU/NIE

(CH3)3In–N(CH3)3

19.9G0.5

83.3G2.1

Derived

1956COA/WHI

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BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1083

23.4.2 InC– and InK–X bonds Table 23.4.2 BDEs of InD– and InL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

InC–In

(1) 45.2 (2) 19.3G7.2

189 81G30

(1) Derived (2) Derived from IP in ref.

(1) 1996SMI/YAT (2) 1996NIST

InC–F

(1) 34G12 (2) 35.4G12

142G50 148G50

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

InC–Cl

(1) 16.6 (2) 46.2G5

69.5 193G21

(1) Review (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

(1) (2) (1) (2)

66.6 65.2G12.6 69.5 51.5G21

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

–Br –I

InC–S

–Se –Te

15.9 15.6G3 16.6 12.3G5

(1) 40G12 (2) 41G12

167G50 171G50

(1) (2) (1) (2)

121G50 118G50 54G50 41G50

29G12 28G12 13G12 9.7G12

InC–Sb

17.5G12

73G50

Derived from IP in ref.

1996NIST

InC–N2

13.8

57.7

PI

1995BRO/DUN

InC–NH3

26.5

111

Derived

1998PAL/SAT

InK–In

(1) 25.1 (2) 39.6G2.9

105 165.5G12

(1) Derived (2) Derived from IP in ref.

(1) 1996SMI/YAT (2) 1996NIST

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1084

Comprehensive Handbook of Chemical Bond Energies

23.5 Tl– and TlG–X bonds 23.5.1 Tl–X bonds Table 23.5.1 BDEs of Tl–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment) kcal/mol Tl–Tl

(1) (2) (3) (4)

FTl–TlF ClTl–TlCl BrTl–TlBr ITl–TlI

12.9 15.4G4 11G1 14.2

kJ/mol

Methods (reference in parentheses)

References

54 64.4G17 46G4 59.4

(1) Review (2) MS (3) Raman (4) Derived from DfH0 in ref.

(1) (2) (3) (4)

32.5G3 24.9G3 22.9G3 20.6G3

136G13 104G13 96G13 86G13

Derived from DfH0 in ref.

1996GUR/VEY

Tl–Hg

(1) 1 (2) 0.7

4 2.9

Est. by exp.

(1) 1950HER (2) 1973LIT/SPA

Tl–Ar –Kr –Xe

0.98 0.99 1.00

4.09 4.14 4.18

Spectroscopy

1998STA/KNI

Tl(O)x–H xZ0 1

46.7G1 118.2G7

195.4G4 495G30

Derived from DfH0 in ref.

1996GUR/VEY

Tl–D

46.1

193.

Spectroscopy

1979HUB/HER

Tl–F

(1) 101G3.5 (2) 105.5G0.5 (3) 105G5

422.6G14.6 441.4G2.1 439G21

(1) MS (2) PI (3) Review

(1) 1966MUR/HIL(b) (2) 1968BER/WAL (3) 1970DAR

7366—CHAPTER 23—3/2/2007—12:03—BSARAVANAN—15379—XML MODEL B – pp. 1041–1086

1979MIE/GIN 1980BAL/PIA 1983FRO/SCH 1988LIA/BAR

BDEs of B(BG)–, Al(AlG)–, Ga(GaG)–, In(InG)–, and Tl(TlG)–X Bonds

1085

Tl–Cl

89.1G0.5

372.8G2.1

PI

1968BER/WAL

Tl–Br

(1) (2) (1) (2)

330.1G2.1 331G21 273.2G2.1 285G21

(1) PI (2) Review

(1) 1968BER/WAL (2) 1970DAR

–I

78.9G0.5 79G5 65.3G0.5 68G5

(O)(Tl)x–Tl xZ0 1

63.3G7 78.2G7

265G30 327G30

Derived from DfH0 in ref.

1996GUR/VEY

Tl–O

51G20

213G84

Review

1983PED/MAR

Tl–OH

78.8G7

330G30

Derived from DfH0 in ref.

1996GUR/VEY

Tl–P

50G3

209G13

MS

1978PIA/BAL

Tl–As

47.4G3.6

198.3G14.6

MS

1972PIA/MAL

Tl–Sb

30.3G2.5

126.7G10.5

MS

1981BAL/FER

Tl–Bi

28.9G3

120.9G12.6

MS

1972MAR/MAL

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Comprehensive Handbook of Chemical Bond Energies

23.5.2 TlC– and TlK–X bonds Table 23.5.2 BDEs of TlD– and TlL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) kcal/mol

kJ/mol

TlC–Tl

5.3G12

22G50

Derived from IP in ref.

1996NIST

TlC–F

(1) 6G5 (2) 3.2G5

25G21 13G21

(1) 1974GUR/KAR (2) 1996NIST

(3) 4.6

19.2

(1) Derived (2) Derived from IP in ref. (3) Derived

(1) 13G2 (2) 6.3G1

54G8 26G4

(1) (2) (1) (2)

42G8 52G50 59G8 133G21

TlC–Cl

–Br –I

TlK–Tl

10G2 12G12 14G2 32G5

28.6G2.4

120G10

Methods (reference in parentheses)

References

(3) 2005SCH/WUL

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

Derived from EA in ref.

1996NIST

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chapter twenty-four

BDEs in the C-, Si-, Ge-, Sn-, Pb-clusters and complexes 24.1 Carbon and the ion clusters/complexes 24.1.1 Carbon clusters/complexes Table 24.1.1 BDEs in Carbon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

C–C in neutral clusters see Section 4.6

C(amorphous)–Ag

19.1

80.0

STM

1980UTL

C(amorphous)–Au

20.3

84.9

STM

1980UTL

C(amorphous)–In

19.4

81.0

STM

1980UTL

2,3-Dimethynaphthalene–He

0.17, at 0 K

0.72

Combined

1997BAC/LEU

C(diamond, 111, surf )–He

0.15, at 0 K

0.62

Scattering

1983VID/FRA

C(graphite)–He

0.28

1.19

Review

1991VID/IHM

CH4–Ne

w0.1, at 0 K

w0.5

Scattering

1987LIU/LUZ

(continued)

1087

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1088

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.1 (continued) BDEs in Carbon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

cyclo-C3H6–Ne

w0.34, at 0 K

w1.44

Spectroscopy

1997XU/JAG

Benzene–Ne

(1) w0.4, at 0 K (2) 0.2

w1.8 0.9

(1) FT MW (2) Spectroscopy

(1) 1994BRU/MAK (2) 1995BET/BET

Fluorene–Ne

R0.7, at 0 K

R2.8

TRPI

1983LEU/EVE

p-Difluorobenzene–Ne

0.34, at 0 K

1.44

UV fluorescence

2004JAY/PAR

C(graphite)–Ne

0.69

2.90

Review

1991VID/IHM

C–Ar

1.233, at 0 K

5.158

Spectroscopy

2000LEI/DAG

C(graphite)–Ar

2.3

9.6

Review

1991VID/IHM

CH4–Ar

w0.3, at 0 K

w1.3

Scattering

1987LIU/LUZ

CH2F2–Ar

w0.4, at 0 K

w1.5

Spectroscopy

2000LOP/FAV

CF2CH2–Ar

0.50, at 0 K

2.10

Spectroscopy

1995BET/BET

cyclo-C3H6–Ar

w0.88, at 0 K

w3.67

Spectroscopy

1997XU/JAG

C6H6–Ar

(1) !0.97, at 0 K (2) w1.2 (3) !0.90 (4) !0.97 (5) 0.90

!4.07 w4.9 !3.78 !4.1 3.76

(1) Spectroscopy (2) FT MW (3) Spectroscopy (4) MATI (5) Spectroscopy

(1) 1993KRA/NEU (2) 1994BRU/MAK (3) 1999SAT/PIE (4) 1999NEU/GRE (5) 2003SAM/LAW

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BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1089

C6H5CHCH2–Ar

1.13, at 0 K

4.74

MPI

1988RAD/EVE

C6H5CH2–Ar

1.29, at 0 K

5.38

Spectra

1993DIS/BER

C6H5F–Ar

(1) 0.92, at 0 K (2) 0.98

3.84 4.11

MATI

(1) 1996GRE/NEU (2) 1997LEM/BRU

C6H5F–2Ar –3Ar

0.99, at 0 K 1.04

4.15 4.35

MATI

1997LEM/BRU

p-C6F2H4–Ar

(1) w1.1, at 0 K (2) 1.64

w4.8 6.84

Spectroscopy

(1) 1986BUT/CAT (2) 2001BEL/MOU

p-F-C6H4CH3–Ar

0.94G0.06, at 0 K

3.94G0.24

MATI

2004GEO/CHA

C6H5CH3–Ar

0.59–0.72, 0 K

2.45–3.00

LIF

1997KEN/HAA

C(graphite, 001, surf.)–Ar

2.3

9.6

Model

1973STE

Perylene–Ar

1.6–2.0, at 0 K

6.7–8.4

Fluorescence

1989WIT/KAZ

t-Stlbene–Ar

1.13–1.70, at 0 K

4.74–7.11

LIF

1990SEM/BAS

Fluorene–Ar

1.5G0.3, at 0 K

6.1G1.1

R2PI

1983LEU/EVE

Anthracene–Ar

0.98–2.04, 0 K

4.09–8.52

LIF

1991MUL/HEI

Tetracene–Ar

!0.78, at 0 K

!3.28

LIF

1981GRI/FRE

CH4–Kr

w0.4, at 0 K

w1.6

Scattering

1987LIU/LUZ

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 24.1.1 (continued) BDEs in Carbon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CH2F2–Kr

0.45, at 0 K

1.9

Spectroscopy

2005MAR/MEL

cyclo-C3H6–Kr

w1.01, at 0 K

w4.24

Spectroscopy

1997XU/JAG

C6H6–Kr

(1) !1.15, at 0 K (2) w1.5 (3) 0.94

4.81 w6.1 3.95

(1) Spectroscopy (2) FT MW (3) Spectroscopy

(1) 1993KRA/NEU (2) 1994BRU/MAK (3) 1995BET/BET

p-C6F2H4–Kr

2.06, at 0 K

8.61

Spectroscopy

2001BEL/MOU

Fluorene–Kr

R2.0, at 0 K

R8.6

Two-photon tech

1983LEU/EVE

C(graphite)–Kr

2.9

12.1

Review

1991VID/IHM

CH2F2–Xe

0.4, at 0 K

1.8

Spectroscopy

2006CAM

CH4–Xe

w0.4, at 0 K

w1.7

Scattering

1987LIU/LUZ

Benzene–Xe

(1) w1.8, at 0 K (2) 1.23

w7.6 5.16

(1) FT MW (2) Spectroscopy

(1) 1994BRU/MAK (2) 1995BET/BET

Fluorene–Xe

R2.1, at 0 K

R8.8

Two-photon tech

1983LEU/EVE

C(graphite)–Xe

3.74

15.6

Review

1991VID/IHM

C(graphite)–H

0.7 (phys)

3.0

Review

1991VID/IHM

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BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1091

C(0001, surf.)–H

(1) 13.8 (2) 14.3

57.9 60

(1) TDS (2) HR-EELS

(1) 2002ZEC/GUT (2) 2005ALL/FER

C(0001, surf.)–D

21.9

91.7

TDS

2002ZEC/GUT

C(graphite)–H2

0.96 (phys)

4.01

Review

1991VID/IHM

C(graphite)–H2

50

209

Review

1964HAY/TRA

CH4–H2

0.08, at 0 K

0.33

IR

1999MCK/ROT

C(graphite)–Cl2

32

134

Review

1964HAY/TRA

C2F4–O2

3.14G0.29, 0 K

13.14G1.21

PI

1997CHE/PRE

C6H6–O2 C6F6–O2

1.6G0.3, at 0 K 2.1G0.4

6.7G1.3 8.8G1.7

PI

1992GRO/HAG

C(graphite)–O2

(1) 2.5 (phys) (2) 2.4

10.5 10.0

(1) G-S CG (2) Virial anal.

(1) 1964GAL/BEE (2) 1987BOJ/STE

C(graphite)–O2

97

406

Review

1964HAY/TRA

C6H6–N2

(1) 0.92G0.07, 0 K (2) 0.87–1.01

3.85G0.29 3.64–4.23

(1) R2PI (2) Review

(1) 1991ERN/KRA (2) 1995GIL/PAR

C6H5CH3–N2

2.25, at 0 K

9.39

R2PI

2003HU/YAN

1,4-C6H4F2–N2

!0.69, at 0 K

!2.87

Spectroscopy

1995GIL/PAR

C(graphite)–N2

(1) 2.5

10.4

(1) Calorimetry

(1) 1983PIP/MOR

(continued)

7366—CHAPTER 24—6/2/2007—13:25—JEBA—15380—XML MODEL B – pp. 1087–1161

1092

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.1 (continued) BDEs in Carbon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 2.4 (3) 2.4

10.0 10.0

(2) Virial anal. (3) Review

(2) 1987BOJ/STE (3) 1991VID/IHM

C(graphite)–NO

2.4

10.1

Adsorption

1974MAT/THO

C2H2–HF

3.11G0.01, 0 K

13.02G0.02

Photofrag.

1999OUD/MOO

C6H6–HF

1.43, at 0 K

5.98

Spectroscopy

1995BET/BET

C2H2–HCl

3.11, at 0 K

13.02

Photofrag.

1999OUD/MIL

C2H4–HCl

(1) !3.18G0.74, 0 K !13.31G3.10 (1) PI (2) 1.5–2.1 6.4–8.7 (2) IR

(1) 1986WAL/GRO (2) 1997HER/EVE

C6H6–HCl

(1) 4.79G0.12, 0 K (2) 1.8–3.8 (3) 2.06 (4) 2.90G0.50

20.04G0.50 7.5–15.9 8.61 12.13G2.09

(1) PI (2) REMPI (3) Spectroscopy (4) Re-cal.

(1) 1985WAL/GRO (2) 1990GOR/GAR (3) 1995BET/BET (4) 2002MON/DIM(b)

Furan–HCl

2.52, at 0 K

10.56

Spectroscopy

1995BET/BET

Ni(110, surf.)CO–CO

1.8 (phys)

7.4

Diffraction

1993XIA/XIE

Benzene–CO

0.60, at 0 K

2.52

Spectroscopy

1995BET/BET

C(graphite)–CO

(1) 2.6 (2) 2.6

10.9 10.9

(1) Adsorption (2) Virial anal.

(1) 1984PIP/MOR (2) 1987BOJ/STE

C6H6–H2O

(1) 1.63–2.78, 0 K

6.8–11.6

(1) Multi-PI

(1) 1992GOT/ZWI

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BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1093

(2) 2.25G0.28 (3) 2.44G0.09

9.45G1.2 10.23G0.39

(2) PI. (3) R2PI

(2) 1995CHE/GRO (3) 1998COU/MON(b)

C6H6–D2O

2.67G0.11, at 0 K

11.17G0.48

R2PI

1998COU/MON(b)

p-F-C6H4F–H2O

2.79G0.03, 0 K

11.66G0.13

R2PI

1995BRE/BAR

C6H5CH3–H2O

2.5G0.1, at 0 K

10.6G0.4

IR

2004MIY/FUJ

Naphthalene–H2O Azulene–H2O

w3.0, at 0 K w25.6

w12.5 w107

PES

2000SCH/KNO

(trans-1-naphthol)–H2O

5.8G0.2, at 0 K

24.3G0.8

MATI

2003BRA/NEU

Anthracene(H2O)x–H2O xZ0 1

1.1, at 0 K 2.3

4.8 9.6

PES

1998PAL/TOP

C(graphite)–H2O

4.3

17.8

G-S CG

1964GEL/BEE

C(graphite, 0001)–H2O

(1) 10.4G0.7 (2) 9.5G0.2

43.4G2.9 39.9G0.8

(1) TPD (2) RAIRS

(1) 1995CHA/OST (2) 2005BOL/WOL(b)

CF2H2–H2O

1.8

7.5

MW spectra

1999CAM/MEL(b)

C6H5CH3–CO2

2.2–2.9, at 0 K

9.5–12.2

LIF

1997KEN/HAA

Perylene–CO2

3.56, at 0 K

14.89

Spectra

1993WIT/TOP

trans-2-C4H8–SO2

3.85G0.23, at 0 K

16.1G1.0

PI

1985GRO/WAL

(continued)

7366—CHAPTER 24—6/2/2007—13:25—JEBA—15380—XML MODEL B – pp. 1087–1161

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Comprehensive Handbook of Chemical Bond Energies

Table 24.1.1 (continued) BDEs in Carbon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

C6H6–SO2

4.40G0.28

18.4G1.2

C(amorphous)–CdCl2

19.8

83.0

STM

1980UTL

C(amorphous)–AuCl3

20.3

84.9

STM

1980UTL

C(graphite)–NH3

5.8 (phys)

24.3

TPD

2005BOL/BRO

C(graphite)–NH3

17

71

Review

1964HAY/TRA

HCN–NH3

2.92, at 0 K

12.21

Review

1995HIL/FRA

CO2–NH3

2.82, at 0 K

11.81

Review

1995HIL/FRA

OCS–NH3

2.81, at 0 K

11.75

Review

1995HIL/FRA

HCCH–NH3

2.81, at 0 K

11.77

Review

1995HIL/FRA

C6H6–NH3

1.84G0.12, 0 K

7.70G0.50

R2PI

2002MON/DIM

C6H5CH3–NH3

1.6–2.3, at 0 K

6.9–9.5

LIF

1997KEN/HAA

C6H5Cl–NH3

2.9G0.5, at 0 K

12.0G2.2

PI

1994GRO/CHE

(1-naphthol)–NH3 –ND3

7.66, at 0 K 8.01

32.06 33.51

R2PI

1995BUR/DRO

C6H6–CHF3

2.0

8.4

Spectroscopy

2006LOP/CAM

7366—CHAPTER 24—6/2/2007—13:25—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1095

CF2H2–CF2H2

1.6

6.6

MW spectra

1999CAM/MAL

Oxirane–CF2H2

2.3

9.6

Spectroscopy

2006BLA/LOP

C6H6–CCl4 –CHCl3 –CH3Cl

2.4–3.2, at 0 K 2.0–4.6 1.5–3.4

10.0–13.4 8.4–19.2 6.3–14.2

REMPI

1990GOR/GAR

C6H6–CH4

1.03–1.13

4.3-4.7

MATI

2006SHI/FUJ

Perylene–CH4

1.78–2.30

7.44–9.62

Review

1993TOP

C(graphite)–CH4

3.6

15

TD

1970THO/DUV

C(amorphous)–AnCl3

20.3

84.9

STM

1980UTL

C(amorphous)–UO2Cl2

19.8

83.0

STM

1980UTL

C(graphite)–CH3OH

7.4

31

TPD

2005BOL/WOL

(1-naphthol)–CH3OH

7.56G0.39, 0 K

31.63G1.63

R2PI

1995BUR/DRO

C6H5CH3–N(CH3)3

3.1G0.6, at 0 K

12.9G2.4

LIF

1997KEN/HAA

Nanotube interior–cis(NO)2

3.6G0.2, at 0 K

15.1G0.7

IR

2003KON/YAT

nC3H7C6H5–CH4 –C2H6 –C3H8

1.5–2.7, at 0 K w2.7 O2.8

6.3–11.2 w11.1 O11.5

Jet spectroscopy

1985LAW/SCH

Perylene–C2H4

2.99, at 0 K

12.50

Spectroscopy

1993WIT/TOP

(continued)

7366—CHAPTER 24—6/2/2007—13:25—JEBA—15380—XML MODEL B – pp. 1087–1161

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Comprehensive Handbook of Chemical Bond Energies

Table 24.1.1 (continued) BDEs in Carbon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

C(amorphous)–C2H6

w1.4 (phys)

w5.9

Scattering

1986COU/BIE

C(amorphous)–C2H6

5.8

24.3

Scattering

1986COU/BIE

CF2CH2–(CH3)2O CF2CFH–(CH3)2O

1.13 1.43

4.76 5.98

FT-MW

2003TAT/OGA

CHF3–oxirane

1.6

6.7

FT-MW

2004ALO/ANT

CHF3–cyclobutanone

1.8

7.5

Spectroscopy

2006OTT/CAM

B–B, BZtrans-2-C4H8

2.9G1.1, at 0 K

12.1G4.6

PI

1985GRO/WAL

C8H18-1-C8H17OH

!6.5, at 0 K

!27.2

IR

2005PAO/SAS

CHF3–dioxane

w1.6

w6.8

FT-MW

2005FAV/GIU

C6H6–C6H6

(1) 1.61G0.23, 0 K (2) 1.66G0.16

6.75G0.96 6.95G0.67

R2PI

(1) 1994NEU/KRA (2) 1998COU/MON(b)

C6H6–cyclohexane –toluene –p-difluorobenzene

1.8G0.5 3.00G0.23 1.84G0.46

7.7G1.9 12.54G0.96 7.72G1.9

R2PI

1994NEU/KRA

C(amorphous)–C6H6

11.5

48.2

TDS

2004ZAC/ULB

C6H6–C6H5Cl C6H5Cl–C6H5Cl

3.23G0.23 3.46G0.23

13.51G0.96 14.47G0.96

R2PI

1996LU/HU

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BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1097

C6H5CH3–SF6

3.57G0.06,at 0 K

14.95G0.24

ZEKE

1999GEP/DES

C6H6–indole

5.21G0.04, at 0 K

21.81G0.18

MATI

1998BRA/GRE

C6H6–3-methylindole

5.02G0.06, at 0 K

20.99G0.24

MATI

2005GEO/NEU

B–B, BZtoluene p-difluorobenzene

3.46G0.23, at 0 K 2.08G0.46

14.47G0.96 8.68G1.93

R2PI

1994NEU/KRA

C2H4–phenol

3.1, at 0 K

13.2

TR-IR-UV

2004KAY/EBA

cyclo-C6H12–phenol

6.92G0.03, at 0 K

28.95G0.13

SEP-R2PI

1997WIC/DRO

C6H6–phenol C6D6–phenol

5.07G0.07, at 0 K 5.08G0.06

21.21G0.29 21.25G0.25

SEP-R2PI

1997WIC/DRO

CH4–C6H5NH2 CH4–4–C2H5–C6H5NH2

1.37, at 0 K 1.66

5.74 6.94

Spectroscopy

1993HIN/BER

CH4–carbazole

1.91, at 0 K

8.00

SEP-R2PI

1995BUR/DRO(b)

C(amorphous)–C8H8

19.6

82.0

TDS

2004ZAC/ULB

(C10H8)(L)x–L, LZC10H8 xZ0 1 2

2.9, at 0 K 8.9 12.1

12.1 37.1 50.7

R2PI

2003FUJ/LIM

(1) 6.9G1.5 (2) 4.2, at 0 K (3) 13G4

28.9G6.3 17.6 54G17

(1) DSC (2) PI (3) Derived

(1) 1981DON/GUA (2) 2004BOU/MIL (3) 2006GRI/DIE

B–B, BZanthracene

(continued)

7366—CHAPTER 24—6/2/2007—13:25—JEBA—15380—XML MODEL B – pp. 1087–1161

1098

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.1 (continued) BDEs in Carbon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

B–B, BZ9decyloxyanthracene

7.1G0.7

29.5G3

DSC

1999GRI/PEY

B–B, BZ9-decylanthracene

6.6G0.7

27.6G3

DSC

1999GRI/PEY

B–B, BZ9-methoxyanthracene 10.3G0.7

43.2G3

DSC

1999GRI/PEY

B–B, BZ9-methoxy10-methyl-anthracene

11.0G0.7

45.9G3

DSC

1999GRI/PEY

C(amorphous)–coronene –ovalene

32.3 48.4

135 203

TDS

2004ZAC/ULB

B–B, BZC60

6.34G1.84, at 0 K

26.53G7.72

MS

2002BRA/MAL

B–B, BZC70

7.22G1.84, at 0 K

30.20G7.72

MS

2002BRA/MAL

7366—CHAPTER 24—6/2/2007—13:25—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1099

24.1.2 Positive carbon-ion clusters/complexes Table 24.1.2 BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment CC–C

CC(C)x–C xZ1 2 3 4 5 6 7 8 9 10

CC(C)x–C2 xZ0 3 7

CC(C)x–C2 xZ39 41 43 45 47

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 148G12 (2) 139G7

619G50 582G29

(3) 143.9G4.6

601.9G19.3

(1) (1) (1) (1) (1) (1) (1) (2) (1) (2) (2)

762G67 608 685 637 753 579 646 523 791 745G96 732G96

(1) MS

(1) 1990PAR

(2) MS

(2) 1989RAD/RIN

(1) 178 (2) 178 (2) 129

743 743 540

MS

(1) 1989RAD/RIN (2) 1990PAR

(1) (2) (1) (2) (1) (2) (1) (2) (1) (2)

891G19.3 830G14.5 909G13.5 849G14.5 906G16.4 830G14.5 924G7.7 859G14.5 960G16.4 878G14.5

(1) KERD (2) MF

(1) 2004GLU/LEU (2) 2005CON/GLU

182G16 145 164 152 180 138 155 125 189 178G23 175G23

213G4.6 198.3G3.5 217G3.2 202.9G3.5 217G3.9 198.3G3.5 221G1.8 205.2G3.5 229G3.9 209.8G3.5

(1) MS (1) 1990PAR (2) Derived from (2) 1996NIST IP in ref. (3) GIB MS (3) 1999LU/TOS

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment 49 51 53 55 57

59 61 63 65 67 69 71 73 75 77

79

81 83 85 87

C2C(C)77 –C2 C3C(C)77 –C2

kcal/mol (1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (3) (4) (5) (1) (2) (1) (2) (1) (2) (1) (2) (1) (1) (1) (1) (1) (1) (5) (6) (1) (5) (6) (1) (1) (1) (1)

207G4.4 204.1G3.5 221G5.8 205G3.5 232G4.4 209.8G3.5 229G4.4 211.0G3.5 245.8G1.8 228.3G3.5 231G4.6 249G6.9 236.4 196.5G3.0 198.3G3.5 202.2G2.5 215.6G4.6 214G2.5 211.0G4.6 219G1.8 214.5G6.9 227G2.5 206G3.0 211G1.8 212G2.5 218G3.7 224.4G2.5 255 217 203G2.5 208 196 205G3.7 210G1.8 209G4.2 224G3.0

214.5G13.3 205.0G8.5

kJ/mol 866G18.3 854G14.5 925G24.1 859G14.5 972G18.3 878G14.5 958G18.3 883G14.5 1028.5G7.7 955G14.5 965G19.3 1042G28.9 989 822.0G12.5 830G14.5 846.2G10.6 902G19.3 896G10.6 883G19.3 918G7.7 897G29 951G10.6 860G12.5 884G7.7 888G10.6 910G15.4 938.8G10.6 1065 907 848G10.6 868 820 858G15.4 877G7.7 876G17.4 939G12.5

897G56 858G36

Methods (reference in parentheses)

References

(3) Review (4) LI (5) KERD

(3) 2001MAT/ECH (4) 2003TOM/AND (5) 2004GLU/FEI

(6) KERDs

(6) 2003PER/CAO

KERD

2004GLU/FEI

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1101

(La)CC(C)77 –C2 (La)C2C(C)77 –C2 (La)C3C(C)77 –C2

215.8G10.8 222.5G11.1 225.1G11.3

903G45 931G46 942G47

KERD

2006FEI/GLU

(La)CC(C)79–C2 (La)C2C(C)79–C2 (La)C3C(C)79–C2

204.1G10.1 204.5G10.1 214.0G10.6

854G43 856G43 895G44

KERD

2006FEI/GLU

ðTiÞ2 CC 78 –C2 ðScÞ3 CC 78 –C2

208 215

868 898

KERDs

2003PER/CAO

ðScÞ3 NCC 78 –C2

252

1055

KERD

2004GLU/FEI

ðLaÞCC 80 –C2 ðTbÞCC 80 –C2

247 318

1032 1331

KERDs

2003PER/CAO

CC(C)x–C3 xZ2 3 4 5 6 7

127 120 120 122 166G23 173G23

531 502 502 511 695G96 724G96

MS

1989RAD/RIN

CC–Ar

(1) 22.5 (2) 17.3

94.2 72.3

(1) MS (2) ICP-MS

(1) 1979HIL/GUE (2) 1994NON/MAT

COC–Ar

23.1G3.5

96.5G14.6

PIPECO

2002WEI/MAH

COC 2 –Ar

6.0

25.1

PD

1983PRA/DEH (continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1102

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment CHC 3 ðArÞx –Ar xZ0 1 2 3 4 5 6 7 N

kcal/mol (1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (1) (2) (3)

11.3G2.0 9.0–16.9 2.26G0.2 !3.0 1.97G0.2 w2.0 1.96G0.2 w2.0 1.94G0.2 w2.0 1.94G0.3 w2.0 1.94G0.4 w2.0 w1.93 w2.0 w1.5

kJ/mol

Methods (reference in parentheses)

References

47.3G8 37.7–70.6 9.5G0.8 !12.6 8.2G0.8 w8.4 8.2G0.8 w8.4 8.2G0.8 w8.4 8.2G1.3 w8.4 8.2G1.7 w8.4 w8.1 w8.4 w6.4

(1) HP MS (2) PD

(1) 1991HIR/KUD(b) (2) 1998OLK/NIZ

(3) Extrapolate

(3) This volume

cyclo-C3 HC 3 –Ar

1.5, at 0 K

6.4

PD

2001SOL/DOP

(C6H6)C–Ar, p-bond

(1) !1.46, at 0 K (2) 1.39 (3) 1.39

!6.12

Spectroscopy

(1) 1993KRA/NEU

5.80 5.81

(2) 1999SAT/PIE (3) 2003SAM/LAW

(C6H5CH2)C–Ar, p-bond 1.46, at 0 K

6.12

MATI

2000GAS/LAW

(C6H5CHCH2)C–Ar

1.46, at 0 K

6.12

Derived

2000KIM

(C6F2H4)C–Ar

1.65, at 0 K

6.89

Spectroscopy

2000BEL/GAS

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1103

(C6H5F)C–Ar

0.92, at 0 K

3.84

Spectroscopy

1996GRE/NEU

( p-F-C6H4CH3)C–Ar

1.46G0.06, at 0K

6.10G0.24

MATI

2004GEO/CHA

COC 2 –Kr

17.1

71.5

PI

1985JAR/ILL(b)

CHC 3 –Kr

(1) 47.7G2.5 (2) 44.0

199.6G10.5 184.1

ICR

(1) 1987HOV/MCM (2) 1988MCM/HEI

(C6H6)C–Kr

!1.82, at 0 K

!7.60

Spectroscopy

1993KRA/NEU

CHC 3 –Xe

(2) 55.2G2.5 (3) 50.9

231.0G10.5 213.0

(1) ICR (2) HP MS

(1) 1986HOV/MCM (2) 1988MCM/HEI

(1) 95.2G0.3

398.3G1.4

CC(H)x–H xZ0

(1) Derived from IP in ref. (2) 95.08G0.01 397.83G0.06 (2) Spectrometry (3) 95 397.5 (3) Derived (4) 95.088G 397.848G0.013 (4) PD 0.003 (5) 90.6 379.1 (5) Spectroscopy (3) 108 451.9 (6) 118.5 495.9 (6) PI (3) 122 510.4 (7) 130.1 544.2 (7) PI (3) 42 175.7 (7) 41.7 174.6 (8) 39.3G0.1 164.5G0.4 (8) PFI-PEPICO

(1) 1996NIST

CCD3–D

40.4G0.1

169.2G0.4

PFI-PEPICO

2001SON/QIA(b)

CC(Cl)x–H xZ1 2

84.4 116.7

353.1 488.2

PI

1996LI/RAN(d)

1 2 3

(2) 1998HEC/AMI (3) 1999KNE/LER (4) 2002HEC/WIL (5) 2004RED/AHA (6) 1996LI/RAN(d) (7) 1997LI/RAN

(8) 1999WEI/MAL

(continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1104

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CC(H)(Cl)x–H xZ1 2

103.1 33.2

431.3 138.9

PI

1996LI/RAN(d)

CBrC–H

113.9G2

476.6G8.4

2004CHI/FAN

HCBrC–H HCBrC 2 –H

118.8G2 39.7G2

497.1G8.4 166.1G8.4

Derived from DfH 0 in ref.

HClFC 2 –H

46.1

193

UV PI

2005YAN/HUA

HCC 2 –H

137.368

574.749

PEI-PEPICO

1999JAR/WEI

[C2H2Cl]C–H

113.5G1.2

474.7G4.8

UV PI

1995SHE/QI

[C2H3O]C–H

29.7G0.5

124.5G1.9

UV PI

1999LIU/QI

CF2 CFC 3 –H

38.7G2.3

162.1G9.6

UV PI

2005YAN/HUA(b)

CHFCFC 3 –H

39.4

165

UV PI

2005HUA/YAN

CH3 CðOÞCHC 2 –H

78.6G0.7

329G2.9

UV PI

2005WEI/YAN

PC(CH3)2CH2–H

59

247

Derived from DfH 0 in ref.

2005BOD/KER

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

C6 HC 5 –H

(1) (2) (3) (4) (5)

C6 HC 4 –H

88.4 89.5 85.3 89.5 89.9G1.2

1105

369.9 374.5 357.0 374.4 376.3G4.8

(1) (2) (3) (4) (5)

Derived Combined Derived TRPD Kinetics

(1) (2) (3) (4) (5)

1992GRA 1993KLI/FAU 1995HO/DUN 1996DUN 2006TRO/USH

96.1

402.1

Derived

1992GRA

C10 HC 7 –H

103.3

432.2

Derived

1995HO/DUN

C7 HC 7 –H C11 HC 9 –H

48.7 55.6

203.6 232.5

TRPD

1993GOT/NAO

86.0G4.8

359.9G20

PIMS

1997LIN/LIF

(1) 172G9.5

721G40

(2) 179 (2) 76 (2) 138

749 318 577

(1) Derived from (1) 1996NIST IP in ref. (2) Derived (2) 1999KNE/LER

(CCl2F)C–F

39.2G5.8

164G24

UV PI

1997SHE/QI

CHClFC–F

47.3

198

UV PI

2005YAN/HUA

CHFCFC 3 –F

69.2G2.3

289G9.6

UV PI

2005YAN/HUA(b)

Triphenylene radical cation H

CC(F)x–F xZ0

1 2

(continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

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Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CH2 CFC 3 –F

57.9

242

UV PI

2005HUA/YAN

CC(H)x–Cl xZ1 2

146.7 131.2

614 549

UV PI

1996LI/RAN(d)

CC(H)x(Cl)–Cl xZ1 2

88.3 18.7

370 78

UV PI

1996LI/RAN(d)

(1) 149.4G2.3 (2) 148.8G5.4

625G9.6 623G23

(1) 1996LI/RAN (2) 1996NIST

(3) 149.2 (4) 163 (1) 62.0G2.3 (3) 56.0 (4) 48 (1) 95.5G2.3 (4) 108 (1)K3.0G2.3

624 682 260G9.6 235 201 399G9.6 452 K12.5G9.6

(1) UV PI (2) Derived from IP in ref. (3) UV PI (4) Derived

(CClF2)C–Cl

4.8G2.3

20.3G9.6

UV PI

1997SHE/QI

CHFC 2 –Cl

6.2

26

UV PI

2005YAN/HUA

C2 HC 3 –Cl

59.0G1.2

247G4.8

UV PI

1996ZHA/SHE

[C3H5O]C–Cl

21.0

87.8

UV PI

2001LIU/LI

CC(Cl)x–Cl xZ0

1

2 3

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

(3) 1997LI/RAN (4) 1999KNE/LER

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1107

o-Cl-C6 HC 4 –Cl p-Cl–C6 HC 4 –Cl

74.3G3.9 76.6G4.2

310.7G16.4 320.3G17.4

CID

2002MUN/HEU

1-C10 HC 15 –Cl

18.4G2.3

77.2G9.6

TPEPICO

2002LI/BAE

CC–Br

(1) 95.2G2.1

398G8.6

(2) 126G4

526G16.7

(1) Derived from (1) 1996NIST IP in ref. (2) Derived from (2) 2004CHI/FAN DfH 0 in ref.

HCC–Br

113.8G2

476G8.4

H2CC–Br

123.7G2

518G8.4

CHC 3 –Br

52.83G0.05

HBrCC–Br

Derived from DfH 0 in ref.

2004CHI/FAN

221.04G0.19

PFI-PE

2001SON/QIA(c)

103.4G2

432.6G8.4

Derived from DfH 0 in ref.

2004CHI/FAN

(CH2Br)C–Br

(1) 22.6 (2) 23.4G2

94.6 98.1G8.4

(1) UV PI (1) 1996LI/RAN(b) (2) Derived from (2) 2004CHI/FAN DfH 0 in ref.

C2 HC 3 –Br

47.9

200.6

TPEPICO

2006LAG/BAE

C2 HC 5 –Br

30.2

126.4

UV PI

1999ZHO/SHE

C6 HC 5 –Br

63.6

266.3

TRPD

1993GOT/NAO

C10 HC 7 –Br

74.5

311.6

TRPD

1993GOT/NAO (continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1108

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment CHC 3 ðCH3 IÞx –I xZ0

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 61.8 258.6 (2) 62.98G0.07 263.50G0.29 (1) 10.8 45.3

(1) UV PI (2) PFI-PE

(1) 19.2G2.0

80.5G8.4

(2) 23.3G0.1

97.6G0.5

(1) Derived from (1) 1996NIST IP in ref. (2) Review (2) 2003AGU/PRA

(1) 193.3 (2) 193.8G0.2

808.8 810.7G0.8

(3) 193.0G4.4

807.5G18.3

(1) Derived (1) 1979HUB/HER (2) Derived from (2) 1996NIST IP in ref. (3) Spectroscopy (3) 2004RED/AHA

[C2H4]C–O

84.6G0.7

354.1G2.9

UV PI

1999LIU/QI

[CH2CCH2]C–3O

328.6

1375

Derived

1998SCH/BLA

CC–S

168.9G0.5

706.6G2.1

Derived from IP 1996NIST in ref.

152G11.7

635G49

CC–N

(1) 111.8 (2) 125.3G1

467.9 524.5G4.2

(1) Derived (1) 1979HUB/HER (2) Derived from (2) 1996NIST IP in ref.

CC 60 –N C70–N

78–205 69–184

328–859 289–772

MIKE

CC–P

140G12

587G50

Derived from IP 1996NIST in ref.

1

CFC 3 –I

CC–O

–Se

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

(1) 1997RAN/SHU (2) 2001SON/QIA(c)

2006CAO/PRE

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

CHC 3 –H2

1109

(1) 40 (2) 44.4

167 186

Review

(1) 1977KEB (2) 1986KEE/CAS

CHC 5 ðH2 Þx –H2 xZ0 1 2 3

1.88G0.1 1.78G0.1 1.61G0.1 1.57G0.1

7.9G0.4 7.4G0.4 6.7G0.4 6.6G0.4

HP MS

1991/HIR/KUD

[C2H2O]C–H2

71.7G0.7

300.1G2.9

UV PI

1999LIU/QI

C2 HC 5 –H2

(1) 11.8 (2) 12.8

49.4 53.6

HP MS

(1) 1976HIR/KEB (2) 1993SZU/MCM

i-C3 HC 7 –H2

!2.5

!11

HP MS

1976HIR/KEB

C6 HC 6 –O2 C6 FC 6 –O2

3.4G0.3, at 0 K 14.2G1.2 3.2G0.4, at 0 K 13.4G1.7

PI

1992GRO/HAG

COC–N2

16.1G4.6

67.5G19.3

Kinetics

1998GLO/BAN

H2CHC(N2)x–N2 xZ0 1 2 3 4

7.6 5.1 3.2 3.1 3.2

31.8 21.3 13.4 13.0 13.4

HP MS

1982SPE/FIT

H3CC(N2)x–N2 xZ0 1 2 3 4 5 6

(1) (2) (2) (2) (2) (2) (2)

202.5 12.1G1.3 11.7G0.8 11.3G1.3 10.5G0.8 9.2G0.8 7.1G0.8

(1) ICR (2) HP MS

(1) 1988MCM/HEI (2) 2003HIR/TAK

48.4 2.9G0.3 2.8G0.2 2.7G0.3 2.5G0.2 2.2G0.2 1.7G0.2

(continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1110

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment 7 N

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(3) Extrapolate

(3) This volume

(2) 1.5G0.4 (3) w1.3

6.3G1.7 w6

CFC 3 ðN2 Þx –N2 xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

29.3 21.3 8.4 7.5 6.3 w6

(1) HP MS

(1) 1996HIR/NAS

(2) Extrapolate

(2) This volume

CHC 5 –N2

6.8

28.5

HP MS

1986KEE/CAS

C2 HC 5 ðN2 Þx –N2 xZ0 1

6.9 4.6

28.9 19.2

HP MS

1983SPE

cyclo-C3 HC 3 –N2 , p-bond cyclo-C3 HC 3 –N2 , s-bond

2.46G0.49 2.57G0.37

10.29G2.03 10.77G1.56

IR PD

2002SOL/DOP

C6H6FC–N2

w2.4

w10

IR PD

2005DOP/SOL

C6 HC 7 –N2

w2.3

w9.6

IR PD

2003SOL/DOP

CHClC–F2

132.8

556

UV PI

2005YAN/HUA

CH2 CFC 2 –F2

172.5

722

UV PI

2005HUA/YAN

CClFC–HF

7.1

30

UV PI

2005YAN/HUA

7.0 5.1 2.0 1.8 1.5 w1.3

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

CHC 3 –HF –HCl –HBr –HI

(1) (1) (2) (1) (2) (1)

35G2 55.1 51.7 61.2 55.4 69.6

1111

146.4G8.4 230.5 216.3 256.1 231.8 291.2

(1) HP MS

(1) 1985MCM/KEB

(2) ICR

(2) 1988MCM/HEI

CFC 3 –HF –HCl –HBr –HI

15.0 19.8 21.3 31.1

62.8 82.8 89.1 130.1

HP MS

1985MCM/KEB

(C6H6)C–HCl

7.3

30.5

PI

1985WAL/GRO

C2 HC 3 –CN

76.6

320.3

UV PI

1999LIU/QI(b)

t-C4 HC 9 –CN

38

159

EI

1970HEE/RIDt

t-C4 HC 9 –NC

4.3, at 0 K

17.9

TREPICO

2004KOI/BAE

CHC 3 –SH

81.4

340.6

Derived

1997CHE/FEN

CH3 CHC 2 –SH

45.2

189.1

Derived

1997CHE/FEN

(1) (2) (4) (4) (2) (5) (5) (5) (5) (5) (5) (5)

106.1 93.7 189.1 173.7G14.6 15.4 52.3 30.2 18.4 17.8 11.3 9.4 6.6

(1) (2) (3) (4)

(1) (2) (3) (4)

COC(CO)x–CO xZ0

1 2 3 4 5 6 7

25.4 22.4 45.2 41.5G3.5 3.7 12.5 7.21 4.40 4.25 2.70 2.25 1.58

Ion reactions PI EI KER

(5) HP MS

1971CHO/FRA 1981LIN/ONO 1994CHE/HOL 2002WEI/MAH

(5) 1991HIR/MOR

(continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1112

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment 8 9 10 11 12 13 14 15 16 N

(HCO)C(CO)x–CO xZ0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 N

CHC 3 ðCOÞx –CO xZ0 1 2 3 4

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(6) Extrapolate

(6) This volume

(1) 1979HIR/SAL (2) 1982JEN/HEA

(5) (5) (5) (5) (5) (5) (5) (5) (5) (6)

1.06 1.85 1.98 2.13 2.10 2.08 1.92 1.92 1.88 w1.8

4.4 7.7 8.3 8.9 8.8 8.7 8.0 8.0 7.9 w7.5

(1) (2) (1) (3) (1) (3) (1) (3) (1) (3) (3) (3) (3) (3) (3) (3) (3) (3) (3) (3) (4)

12.8 10.8 6.6 4.89 6.3 4.66 6.2 4.46 5.8 4.42 2.39 2.27 2.20 2.11 2.00 1.96 1.89 1.84 1.79 1.76 w1.8

53.6 45.2 27.6 20.5 26.4 19.5 25.9 18.7 24.3 18.5 10.0 9.5 9.2 8.8 8.4 8.2 7.9 7.7 7.5 7.4 w7.5

HP MS

(4) Extrapolate

(4) This volume

(1) (1) (1) (1) (1)

70.6 4.5 4.3 4.1 3.1

295.4 18.8 18.0 17.2 13.0

HP MS

1997HIR/KAT

(3) 1989HIR/MOR(e)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

5 6 N

(1) 2.4 (1) 2.3 (2) w1.8

10.0 9.6 w7.5

CFC 3 ðCOÞx –CO xZ0 1 2 3 4 5 6

16.0 6.3 5.8 5.4 3.2 2.9 2.6

C2 HC 4 –CO

(HCO)C(CO2)x–CO2 xZ0 1 2 3

(CO2)C(CO2)x–CO2 xZ0

1

2

3 4 5 N

CHC 3 –CO2

1113

(2) Extrapolate

(2) This volume

66.9 26.4 24.3 22.6 13.4 12.1 10.9

HP MS

1996HIR/NAS

228.5

956

Derived

1998BLA

12.6 7.2 6.9 8.4

52.7 30.1 28.9 35.1

HP MS

1986HIR/SHO

(1) (2) (3) (4) (5) (1) (2) (3) (5) (2) (3) (5) (3) (3) (3) (6)

67.8 65.3 65.3G4.2 66.5 70.3 25.1 31.0 23.4G1.3 34.7 25.1 21.3G1.3 21.3 20.1G1.3 18.0G1.7 w6.7 w24

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

(6) Extrapolate

(6) This volume

206.7

ICR

1988MCM/HEI

16.2 15.6 15.6G1.0 15.9 16.8 6.0 7.4 5.6G0.3 8.3 6.0 5.1G0.3 5.1 4.8G0.3 4.3G0.4 w4.0 w5.7

49.4

HP HP HP HP EI

MS MS MS MS

1977MEO/FIE(b) 1982STE/FUT 1988HIR/NAK 1988ILL 1994CAM/AIT

(continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1114

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

C2 HC 5 ðCO2 Þx –CO2 xZ0 1 2 3

6.5G0.2 4.9G2 3.9G2 3.7G0.3

27.2G0.8 20.5G8 16.3G8 15.5G1.3

HP MS

2003HIR/SHO

C3 HC 7 –CO2

5.05

21.1

HP MS

1994HIR/YAM

i-C3 HC 7 ðCO2 Þx –CO2 xZ0 1 2

4.8G0.2 4.5G0.2 4.4G0.3

20.1G0.8 18.8G0.8 18.4G1.3

HP MS

2003HIR/SHO

s-C4 HC 9 ðCO2 Þx –CO2 xZ0 1

4.34 w3.6

18.2 w15

Review

1994HIR/YAM

t-C4 HC 9 ðCO2 Þx –CO2 xZ0 1

3.9G0.2 3.8G0.3

16.3G0.8 15.9G0.8

HP MS

2003HIR/SHO

CHC 3 –N2 O

52.9

221.3

ICR

1988MCM/HEI

C2 HC 5 ðN2 OÞx –N2 O xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

49.0G0.8 23.4G0.8 19.2G0.8 17.2G2.1 w17 w17

(1) HP MS

(1) 2003HIR/SHO

(2) Extrapolate

(2) This volume

i-C3 HC 7 ðN2 OÞx –N2 O xZ0 1

(1) 5.5G0.2 (1) 5.4G0.2

(1) HP MS

(1) 2003HIR/SHO

11.7G0.2 5.6G0.2 4.6G0.2 4.1G0.5 w4.0 w4

23.0G0.8 22.6G0.8

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

2 3 N

(1) 4.5G0.2 (1) 3.9G0.2 (2) w4

18.8G0.8 16.3G0.8 w17

t-C4 HC 9 ðN2 OÞx –N2 O xZ0 1 2 N

(1) (1) (1) (2)

22.2G0.8 21.8G0.8 20.5G1.3 w17

NH2 C6 HC 5 –NO2

63.2

(1) (2) (1) (2) (1) (1)

H2CHC(HCN)x–HCN xZ0 1 2 3

5.3G0.2 5.2G0.2 4.9G0.3 w4

30.1 26.1 13.8 14.4 11.8 9.2

1115

(2) Extrapolate

(2) This volume

(1) HP MS

(1) 2003HIR/SHO

(2) Extrapolate

(2) This volume

264.4

UV PI

1997WU/SHE

126 109 58 60 49 39

HP MS

(1) 1978MEO (2) 1986KEE/CAS

H2CHC(NH3)–HCN

w22

w92

HP MS

1986KEE/CAS

RC–HCN RZn-C3H7 i-C3H7 t-C4H9

(1) 39.6 (2) 30.8 (2) 16.3

165.7 128.9 68.2

HP MS

(1) 1991MEO/SIE (2) 1978MEO(b)

RC–CNH RZCH3 C2H5 C2H3 tC4H9 C6H5

117.8G2.3 75.6G1.2 91.8G1.2 48.7G1.4 92.9G0.9

493.0G9.6 316.5G4.8 384.0G4.8 203.7G5.8 388.8G3.9

CID

2000WEN

CHC 3 –SO2

60.6

253.6

ICR

1988MCM/HEI

(trans-2-C4H8)C–SO2

2.4G1.2

10G5

PI

1985GRO/WAL (continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1116

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CHC 3 –OCS –CS2

57.2 60.2

239.3 251.9

ICR

1988MCM/HEI

(C6H6)C–CS2

12.2

51.0

HP MS

1977MEO/FIE

C2 HC 5 ðOCSÞx –OCS xZ0 1 2 3 4 5 6 7 N

(1) (1) (1) (1) (1) (1) (1) (1) (2)

24.9G2.0 7.1G0.3 6.5G0.3 5.8G0.3 w5.5 5.3G0.3 5.2G0.2 4.7G0.4 w4.4

104.2G8.4 29.7G1.3 27.2G1.3 24.3G1.3 w23.0 22.2G1.3 21.8G0.8 19.7G1.7 w18.5

(1) HP MS

(1) 2005HIR/FUJ(b)

(2) Extrapolate

(2) This volume

(1) (1) (2) (2) (2) (2) (2) (2) (2) (3)

66.6 25 25.4 21.0 14.8 11.6 9.1 9.4 8.9 w10.5

279 105 106.3 87.9 61.9 48.5 38.1 39.3 37.2 w44

(1) Review

(1) 1986KEE/CAS

(2) HP MS

(2) 1984MEO

(3) Extrapolate

(3) This volume

42.5

177.8

Ion reactions

1972BEN/FIE(b)

(1) (1) (1) (2)

155 100 80.3 78.2

(1) HP MS

(1) 1977KEB

(2) HP MS

(2) 1986KEE/CAS

CHC 3 ðH2 OÞx –H2 O xZ0 1 2 3 4 5 6 7 N

CHC 5 –H2 O

C2HC 5 (H2O)x–H2O xZ0 1 2

37 24 19.2 18.7

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

3 4 5 6 N

(1) (2) (1) (2) (2) (1) (3)

14.2 13.4 12.5 11.3 9.7 13.1 w10.5

1117

59.4 56.1 52.3 47.3 40.6 54.8 w44

(3) Extrapolate

(3) This volume

C2 HC 6 –H2 O

10.4

43.5

CID

1984HOL/MOM

n-C3 HC 7 ðH2 OÞx –H2 O xZ2 3 4 5 6

17.9 13.0 11.0 9.5 8.8

74.9 54.4 46.0 39.7 36.8

HP MS

1986KEE/CAS

(1) (2) (1) (1) (3) (3) (3) (3) (3) (3) (4)

73.6 95.4 56.5 62.3 68.6 52.3 43.9 40.2 36.8 w33 w44

HP MS

(1) 1971BEG/FIE (2) 1977KEB

(4) Extrapolate

(4) This volume

i-C3 HC 7 ðH2 OÞx –H2 O xZ0 1 2 3 4 5 6 7 N

17.6 22.8 13.5 14.9 16.4 12.5 10.5 9.6 8.8 w7.9 w10.5

(3) 1986KEE/CAS

t-C4 HC 9 ðH2 OÞx –H2 O xZ0 2 3

11.2 17.7 14

46.9 74.1 59

HP MS

1977HIR/KEB

RCOC–H2O RZCH3 C2H5 C6H5

24.6 23.7 25.8

102.9 99.2 107.9

HP MS

1979DAV/MEZ

(continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1118

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment C6 HC 6 ðH2 OÞx –H2 O xZ0

1 2 3 4 5 6 7 N

kcal/mol (1) (2) (3) (3) (3) (3) (3) (3) (3) (3) (4)

4.0G0.4 14G3 9.0G1 8.0G1 8G1 10.3G1 8.6G1 7.8G1 9.8G1 11.1G1 w10.5

Methods (reference in parentheses)

References

16.7G1.7 59G13 37.7G4 33.5G4 33G4 43.1G4 36.0G4 32.6G4 41.0G4 46.4G4 w44

(1) PI (2) IR PD (3) Ion mobility

(1) 1995CHE/GRO (2) 2001SOL/DOP(b) (3) 2005IBR/MEO

(4) Extrapolate

(4) This volume

kJ/mol

C6H5FC–H2O

w9G1

w38G4

IR PD

2005LOR/SOL

C6 HC 7 –H2 O

!17

!71

Review

1986KEE/CAS

C6 H5 CHC 3 –H2 O

9.4G0.3

39.4G1.4

IR PD

2004MIY/FUJ

(trans-1-naphthol)C– H2O

15.9G0.2

66.4G0.8

MATI

2003BRA/NEU

CHC 3 –H2 S CHC 5 –H2 S

82.4 42.1

344.8 176.1

Review

1986KEE/CAS

sec-C3 HC 7 –H2 S

32.0

133.9

HP MS

1991MEO/SIE

C4 HC 6 –H2 S C4 HC 8 –H2 S

3.7 2.4

15.5 10.0

PI

1985GRO/WAL

t-C4 HC 9 –H2 S

47.4

198.3

HP MS

1991MEO/SIE

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1119

[CH2O]C–CH2

86.2G2.3

360.8G9.6

UV PI

1999LIU/LI

CHC 2 –CH2 O

72.4G0.7

303.0G2.9

UV PI

1999LIU/QI

C2 HC 2 –CH2 O

291

1218

Derived

1998BLA

RC–NH3 RZCH3 CH5 C2H5

103.1 75.6 70.1

431.4 316.3 293.3

Review

1986KEE/CAS

t-C4 HC 9 –NH3

(1) 46.5 (2) 45.3

194.6 189.5

HP MS

(1) 1990MEO/SIE (2) 1991SZU/MCM

C6H5ClC–NH3

10.4G0.7

43.5G2.9

PI

1994GRO/CHE

CHC 3 –NF3 –SO2F2 –SO2Cl2

53.6 55.3 62.1

224 231 260

ICR

1988MCM/HEI

CFC 3 –CHF2

24.0G2.3

100.3G9.6

UV PI

2005YAN/HUA

CHFC 2 –CF3

18.4G2.3

77.2G9.6

UV PI

2005YAN/HUA

CH2FC–CF3

11.3

47.3

UV PI

2005HUA/YAN

CHFC 2 –CHF2

80.7

338

UV PI

2005HUA/YAN

CFC 3 –CH2 F

9.7

40.5

UV PI

2005HUA/YAN

(CH3)C–CH3

50G1

209.2G4.2

Derived

1990CAM (continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1120

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(CH2Br)C–CH3

67.1

281

UV PI

1999ZHO/WU

(CH3CO)C–CH3

(1) 19.7G0.02 (2) 18.4G0.5

82.5G1.0 77.2G1.9

(1) TPEPICO (2) UV PI

(1) 2004FOG/KOI (2) 2005WEI/YAN

(CH2CHO)C–CH3

72.2G0.7

302.0G2.9

UV PI

2005WEI/YAN

(H2NCH2)C–B, BZCH3 (HOCH2)C–B (C6H5CH2)C–B

20G6 18G3 (1) 41G4 (2) 40.2G0.3

84G25 75.3G12.6 172G16.7 168.3G1.2

Derived

1990CAM

Derived

(1) 1990CAM (2) 2005FER/VIG

4-Me-C6 H4 CHCHC 3 –CH3 32G2

134G8

FT-ICR

2003SEN/RIV

2;4-ðtBuÞ2 -C6 H3 CðCH3 ÞC 2 –CH3

27.7

116

TRPD

1996DUN

CHC 3 –CH4

39.8

166.5

Review

1986KEE/CAS

CFC 3 –CH4

4.6

19.0

HP MS

1972BEN/FIE(c)

17.2 31.0 28.7G1.3 24.7 22.3G1.3 17.2 13.1G08 16.3 12.6G0.8

HP MS

(1) 1971FIE/BEG (2) 1975HIR/KEB(b) (3) 1989HIR/MOR(d)

(CH5)C(CH4)x–CH4 xZ0

1 2 3

(1) (2) (3) (2) (3) (2) (3) (2) (3)

4.1 7.4 6.87G0.3 5.9 5.34G0.3 4.1 3.14G0.2 3.9 3.02G0.2

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

4 5 6 7 8 N

(C2H5)C(CH4)x–CH4 xZ0

1 2 3 4 5 6 7 8 9 N

(i-C3H7)C(CH4)x–CH4 xZ0 1 2 3 4 5 6 7 N

(t-C4H9)C(CH4)x–CH4 xZ0 1 2 3 4 5 6 7

(3) (3) (3) (3) (3) (4)

2.79G0.2 2.71G0.2 2.67G0.2 2.04G0.2 1.54 w2

11.7G0.8 11.3G0.8 11.2G0.8 8.5G0.8 6.4 w8.4

(1) (2) (3) (3) (3) (3) (3) (3) (2) (2) (2) (2) (4)

2.4 6.6 5.50 2.37 2.28 2.26 2.22 2.21 2.13 2.10 2.08 w1.91 w2

(1) (2) (2) (2) (2) (2) (2) (2) (2) (3)

(1) (1) (1) (1) (1) (1) (1) (1)

1121

(4) Extrapolate

(4) This volume

10.0 27.6 23.0 9.9 9.5 9.5 9.3 9.2 8.9 8.8 8.7 w8 w8

HP MS

(1) 1971FIE/BEG (2) 1975HIR/KEB(c) (3) 1994HIR/YAM

(4) Extrapolate

(4) This volume

3.4 2.59 2.45 2.26 2.20 2.20 2.19 2.16 w1.98 w2

14.2 10.8 10.3 9.5 9.2 9.2 9.2 9.0 w8.3 w8

HP MS

(1) 1976HIR/KEB (2) 1994HIR/YAM

(3) Extrapolate

(3) This volume

2.48 2.39 2.37 2.36 2.21 2.09 2.05 1.99

10.4 10.0 9.9 9.9 9.2 8.7 8.6 8.3

(1) Review

1994HIR/YAM

(continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1122

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment 8 N

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) Extrapolate

(2) This volume

(1) w1.86 (2) w2

w7.8 w8

C6 HC 6 –CH4 C6 HC 7 –CH4

2.9 2.7

12.0 11.4

PD

2003SOL/DOP

CFC 3 ðCF4 Þx –CF4 xZ0 1 2 3 N

(1) (1) (1) (1) (2)

6.6 4.9 2.9 2.8 w2.8

27.6 20.5 12.1 11.7 w12

(1) HP MS

(1) 1996HIR/NAS

(2) Extrapolate

(2) This volume

CF4HC(CF4)x–CF4 xZ0 1 2 3 N

(1) (1) (1) (1) (2)

5.1 2.8 2.3 w2.3 w2.8

21.3 11.7 9.6 w9.6 w12

(1) HP MS

(1) 1996HIR/NAS

(2) Extrapolate

(2) This volume

tC4 HC 9 –CF4 tC4 HC 9 –CHF3

3.4 6.8

14.2 28.5

HP MS

1985SHA/HOJ

CHC 3 –CH3 F –CH3Br

54.9 63.3

230 265

ICR

1988MCM/HEI

CHC 3 –CF3 Cl –CF3Br –CF3I

52.9 53.6 60.0

221 224 251

ICR

1988MCM/HEI

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1123

CH2ClC(CH3Cl)x– CH3Cl xZ0 1 N

(1) 6.9 (1) 5.7 (2) w4.8

28.9 23.8 w20

(1) HP MS

(1) 1974LUC/MAL

(2) Extrapolate

(2) This volume

CHC 3 ðCH3 ClÞx –CH3 Cl xZ0 1 2 N

(1) (2) (2) (3)

259 25.1 21.3 w20

(1) ICR (2) HP MS

(1) 1988MCM/HEI (2) 1974LUC/MAL

(3) Extrapolate

(3) This volume

RC–CH3Cl RZC2H5 i-C3H7 t-C4H9

(1) 30.7 (1) 22.9 (2) 13.8

128 95.8 57.7

HP MS

(1) 1978SHA/KEB

RC–CH2Cl2 RZC2H5 i-C3H7 t-C4H9 t-C5H11 c-C5H11 2-norbornyl

36.0 15.6 9.5 9.5 9.8 10.6

151 65.3 39.7 39.7 41.0 44.4

HP MS

1985SHA/HOJ

t-C4 HC 9 –CHCl3

9.1

38.1

HP MS

1985SHA/HOJ

(aniline)C–CH3I

9.7

40.6

HP MS

1986MEO/ELS

ðC2 H2 ÞC x –C2 H2 xZ1 2

22.5G1 14.4G1

94.1G4.2 60.2G4.2

PI

1991NG

C8 HC 6 –C2 H2

106.3

444.8

Derived

1995HO/DUN

tC4 HC 9 –CH3 OH

(1) 15–21 (2) 15.1

63–88 63

HP MS

(1) 1996NOR/MCM (2) 2001MCM

62.0 6.0 5.1 w4.8

(2) 1985SHA/HOJ

(continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1124

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment tC4 HC 9 –CH3 CN

H2CCCN(CH3CN)x– CH3CN xZ1 2 3 4 N

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 20.4–35 (2) 20.4

85–146 85

HP MS

(1) 1996NOR/MCM (2) 2001MCM

(1) (1) (1) (1) (2)

61.1G1.3 52.3G2.5 48.5G4.2 40.2G4.2 w33

(1) HP MS

(1) 1998WIN(b)

(2) Extrapolate

(2) This volume

14.6G0.3 12.5G0.6 11.6G1 9.6G1 w7.9

C

C3H4N(CH3CN)x– CH3CN xZ1 2 3 4

25.4G0.6 14.8G0.3 12.0G0.8 10.7G0.9

106.3G2.5 61.9G1.3 50.2G3.3 44.8G3.8

HP MS

1998WIN(b)

(C6H6)C(CH3CN)x– CH3CN xZ0 1

13.7 11.4

57.3 47.7

Re-anal.

1996DAL/MEO

(C6H5CH3)C–CH3CN

12.9

54.0

Re-anal.

1996DAL/MEO

(aniline)C–CH3CN

17.3

72.4

HP MS

1986MEO/ELS

(1-CH3-naphthalene)C– CH3CN

11.3

47.3

HP MS

1987ELS/MEO

(HOCH2)C–CH2OH

20G5

84G21

Derived

1990CAM

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1125

(H2NCH2)C–CH2OH –CH2NH2

14G9 22G12

59G38 92G50

Derived

1990CAM

(aniline)C–CH3NO2

14.4

60.2

HP MS

1986MEO/ELS

(1-CH3-naphthalene)C– CH3NO2

11.2

46.9

HP MS

1987ELS/MEO

t-C4 HC 9 –SO2 F2

10.4

43.5

HP MS

1985SHA/HOJ

(1) (2) (1) (2) (2)

76.1 66.1G4.2 17.6 38.5G4.2 19.2G4.2

PI

(1) 1979CEY/TIE(b) (2) 1991NG

C2 HC 4 ðC2 H4 Þx –C2 H4 xZ0 1 2

18.2 15.8G1 4.2 9.2G1 4.6G1

C3 HC 5 –C2 H4 C4 HC 7 –C2 H4

16.7 8.7

69.9 36.4

PI

1979CEY/TIE(b)

[CH2O]C–C2H4

24.9G0.5

104.2G1.9

UV PI

1999LIU/SHE

CF2 CHC 2 –CF2 CH2

42.7G4.6

178.5G19

Kinetics

1994FAU/DUN

CHC 3 –C2 H3 O

80.9G0.7

338.7G2.9

UV PI

1999LIU/SHE

C7 HC 7 –C2 H5

39.9G0.5

166.9G2.2

Kinetics

2004FER/VIG

CH3 OCHC 2 –CH2 OCH3

15.2

63.7

UV PI

2003WAN/WU

CHC 3 –CF3 ClOCl –CF3COCF3

60.1 58.5

252 245

ICR

1988MCM/HEI (continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1126

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(C2H5)C–C2H5 (C6H5CH2)C–C2H5

31G3 40G4

130G12.6 167G16.7

Derived

1990CAM

C2 HC 4 –C2 H6

15.3

64.0

HP MS

1980HIR/KEB

CHC 3 –C2 H5 Cl

71

297

HP MS

1985SHA/HOJ

C2 HC 5 ðLÞx –L, LZC2H5Cl xZ1 5.2 2 4.8

21.8 20.1

HP MS

1974LUC/WIN

C2 HC 5 –C2 H5 Cl

71

297

Derived

1985SHA/HOJ

t-C4 HC 9 –C2 H5 Cl

9.2

38.5

HP MS

1985SHA/MEZ

t-C4 HC 9 –ðCH3 Þ2 S

44.2

185

HP MS

1991MEO/SIE

C2 HC 5 –C2 H5 OH

54

226

Ion reactions

1977HIR/KEB(c)

tC4 HC 9 –C2 H5 OH

(1) (2) (1) (2) (1) (2)

85–161 85 97–139 97 80–140 80

HP MS

(1) 1996NOR/MCM (2) 2001MCM

w41

HP MS

2002HIR/TAK

–CH3OCH3 –CH3COCH3

C2 FC 4 ðC3 F6 Þ–C3 F6

20.4–38.6 20.4 23.2–33.2 23.2 19.2–33.5 19.2

w9.8

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1127

C3 FC 5 ðLÞx –L, LZC3F6 xZ0 1

9.2G0.3 8.2G0.3

38.5G1.3 34.3G1.3

HP MS

2002HIR/TAK

C3 FC 6 ðC3 F6 Þ–C3 F6

w8.9

w37

HP MS

2002HIR/TAK

C3 HC 6 –C3 H6

9.9

41.4

PI

1991NG

C7 HC 8 –C3 H6

(1) 29.5G1.4 (2) 26.3G0.5

123.5G5.8 110.0G1.9

(1) CID (1) 2003MUN/ARM (2) Ion flow tube (2) 2006FER/VIG

C7 HC 7 –nC3 H7

(1) 39.2G2.1 (2) 41.0G1.2

164.0G8.7 171.7G4.8

(1) CID (2) Kinetics

(1) 2003MUN/ARM (2) 2006TRO/USH

i-C3 HC 7 –i-C3 H7 PhCHC 2 –i-C3 H7

23G3 41G4

96.2G12.6 171.5G16.7

Derived

1990CAM

i-C3 HC 7 –i-C3 H7 Cl

77

322

Derived

1985SHA/HOJ

cyclo-C3 HC 6 –cyclo-C3 H6

3.2

13.4

PI

1991NG

s-C3 HC 7 –C3 H8 t-C4 HC 9 –C3 H8

13.6 6.6

56.9 27.6

HP MS

1989SUN/HIR

t-C4 HC 9 ðLÞx iC4H8 xZ0 1

22.9G1 24.2G1.4

95.8G4 101.3G6

HP MS

1995MEO/SIE

t-C4 HC 9 –t-C4 H9 Cl

81

339

Derived

1985SHA/HOJ

t-C4 HC 9 –ðCH3 Þ3 CH t-C4 DC 9 –ðCD3 Þ3 CH

(1) 7.2 (2) 7G0.7

30.1 29.3G2.9

HP MS

(1) 1989SUN/HIR (2) 1987MEO(b)

L, LZ

(continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1128

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(C6H6)C– CH3CO(O)C2H5

12.6

52.7

Re-anal.

1996DAL/MEO

tC4 HC 9 –CH3 CH2 OCH2 CH3

(1) 33.7–46.3 (2) 33.7

141–194 141

HP MS

(1) 1996NOR/MCM (2) 2001MCM

C3 FC 3 –c-C5 F8 C4 FC 5 –c-C5 F8 C4 FC 6 –c-C5 F8 C5 FC 7 –c-C5 F8 C5 FC 8 –c-C5 F8

9.3G0.3 9.2G0.4 9.6G0.3 9.4G0.2 10.3G0.3

38.9G1.3 38.5G1.7 40.2G1.3 39.3G0.8 43.1G1.3

MS

2005HIR/FUJ

(C6H6)C–c-C6H12

(1) 9.9 (2) 4.6G0.9

41.4 19.3G3.9

(1) HP MS (2) R2PI

(1) 1978MEO/HAM (2) 1994NEU/KRA

(p-NH2-C6H4N2)C–C6H5 49.1

206

UV PI

1999WU/SHE

PhCHC 2 –C6 H5

64G5

268G21

Derived

1990CAM

C2 HC 5 –C6 H6

46.5

195

Ion reactions

1982SHA/IKU

cyclo-C3 HC 3 –C6 H6

9.0

37.7

HP MS

1969FIE/HAM

i-C3 HC 7 –C6 H6 t-C4 HC 9 –C6 H6

33.8 22

141 92

Ion reactions

1982SHA/IKU

71.1 86.2G4

(1) HP MS (2) HP MS

(1) 1978MEO/HAM (2) 1991HIR/FUJ

(C6H6)C(L)x–L, LZC6H6 xZ0 (1) 17.0 (2) 20.6G1.0

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1 2 N

(3) (4) (5) (2) (2) (6)

15.2G0.5 17.8 17.6 7.8G0.5 w7.0 w8

1129

63.7G1.9 74.5 73.6 32.6G2 w29 w33

(3) R2PI (4) Re-anal. (5) Ion mobility

(3) 1994NEU/KRA (4) 1996DAL/MEO (5) 2003RUS/IBR

(6) Extrapolate

(6) This volume

(C6D6)C–C6D6

17.4

72.8

Ion mobility

2003RUS/IBR

(C6H6)C(L)x–L, LZC6H6 xZ5 6 7 8 9 10 11 12 13 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

35.6 34.7 33.6 33.1 32.8 32.8 33.3 34.8 34.0 w33

(1) Photofrag.

(1) 1992BEC/HEC

(2) Extrapolate

(2) This volume

(C6H6)HC–C6H6

11.0

46.0

HP MS

1980MEO

RC–C6H6 RZC6H5Cl C6H7 Mesitylene

14.0 11.0 10.6

58.6 46.0 44.4

HP MS

1978MEO/HAM

(1) 12.4 (2) 12.2G0.5

51.9 51.1G1.9

(1) HP MS (2) R2PI

(1) 1978MEO/HAM (2) 1994NEU/KRA

11.9 12.3 10.0

49.8 51.5 41.8

HP MS

1986MEO/ELS

11.2

46.9

9.0

37.7

HP MS

1987ELS/MEO

(CH3C6H5)C–C6H6

RHC–C6H6 RHZaniline N-methylaniline N,Ndimethylaniline N,N-diethylaniline

1-CH3-naphthaleneC –C6H6

8.5 8.3 8.0 7.9 7.8 7.8 8.0 8.3 8.1 w8

(continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1130

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(C2H5)C–OC6H5

63G1

264G4

Derived

1990CAM

(C6H6)C–C6H5F –1,2-C6H4F2 –1,3-C6H4F2 –1,3,5-C6H3F3 –1,2,4,5-C6H2F4 –1,2,3,5-C6H2F4 –C6HF5 –C6F6

17.0 15.2 13.9 12.4 12.0 11.2 11.2 12.1

71.1 63.6 58.2 51.9 50.2 46.9 46.9 50.6

HP MS

1978MEO/HAM

(C6H6)C–pdifluorobenzene

8.8G0.9

36.7G3.9

R2PI

1994NEU/KRA

(C6H6)C–indole

13.1

54.8

R2PI

2003BRA/NEU

(C6H5F)C–C6H5F

(1) 14.1 (2) 7.1

59.0 29.7

(1) HP MS (2) PI

(1) 1978MEO/HAM (2) 1986RUH/BIS

(1,3-C6H4F2)C–1,3C6H4F2

13.2

55.2

HP MS

1978MEO/HAM

(1,4-C6H4F2)C–1,4C6H4F2

8.8

36.8

Multi-PI

1990ERN/KRA

(C6H6)C–1,2,3,5-C6H2F4

11.2

46.9

HP MS

1987ELS/MEO

C6 FC 6 –C6 F6

7.2G1

30.1G4

HP MS

1990HIR/MIZ

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1131

(aniline)C–C6H5X xZH F Cl Br I CN NO2 n-Bu

13.7 11.7 11.7 13.6 13.3 19.4 17.7 13.9

57.3 49.0 49.0 56.9 55.6 81.2 74.1 58.2

HP MS

1986MEO/ELS

MesityleneC–C6H5Cl

11.4

47.7

HP MS

1978MEO/HAM

(tC4H9)C–CH2Ph (CH2Ph)C–CH2Ph

63G1 29G6

264G4 121G25

Derived

1990CAM

1-CH3-naphthaleneC –C6H5CN –C6H5NO2

14.7 13.1

61.5 54.8

HP MS

1987ELS/MEO

(aniline)C–p-xylene –mestitylene –1,1,1-trifluoro toluene –hexafluoro benzene –hexame thylbenze

14.2 15.3 11.8

59.4 64.0 49.4

HP MS

1986MEO/ELS

11.3

47.3

17.1

71.5

(CH3)3CC–C6H5CH3 –C6D5CD3

29.1 28.6

122 120

HP MS

1991STO/STO

(CH3C6H5)C–C6H5CH3

14.5G0.5

60.8G1.9

R2PI

1994NEU/KRA

(CH3C6H5)C–CH3C6H5 (mesitylene)C –CH3C6H5

16.0

66.9

HP MS

1978MEO/HAM

12.0

50.2 (continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1132

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

14.3 (p-xylene)C–p-xylene (mesitylene)C–p-xylene 14.9 (mesitylene)C–m-xylene 14.3

59.8 62.3 59.8

HP MS

1978MEO/HAM

(aniline)C–naphthalene –acenaph thene –acenaph thylene –1-Br-naph thalene –1-Me-naph thalene –azulene

(1) 15.4 (2) 17.5

64.4 73.2

HP MS

(1) 1987ELS/MEO (2) 1986MEO/ELS

(2) 17.2

72.0

(1) 15.8

66.1

(1) 15.8

66.1

(2) 14.0

58.6

C6 HC 5 –N2 C6 H5

61.6

258

UV PI

1998SHE/WU

C6 HC 5 –N2 C6 H4 -p-OH

49.8G1.2

208G4.8

UV PI

2001CHE/ZHA

p-OH-C6 HC 4 –N2 C6 H5

75.9G1.2

317G4.8

UV PI

2001CHE/ZHA

p-NH2 -C6 HC 4 –N2 C6 H5 –N –O–C C6 HC 2 6 H5 5

97.1G1.2 127.8G2.3

406G4.8 535G9.6

UV PI

1999WU/SHE

C2 HC 5 –O-C6 H4 NO2

124.5G2.3

521G9.6

UV PI

2000WU/ZHO

CHC 3 –SðHÞC6 H5 –S(CH3)C6H5 –o-C6H5SCH3 –m-C6H5SCH3 –p-C6H5SCH3

94.9G2.9 108.5G2.9 97.8G2.9 85.1G2.9 101.1G2.9

397G12 454G12 409G12 356G12 423G12

Combined

2003NAM/FLA

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

(C10H8)C(C10H8)x–C10H8 xZ0 15.7 1 21.9 2 26.5

1133

65.6 91.7 111

R2PI

2003FUJ/LIM

HP MS

1969FIE

C3 HC 3 –B, BZ CH3CO2CH2C6H5 BHC–B

10

42

5.4

23

BC–B, BZalinine N-methylaniline N,N-dimethylaniline N,N-diethylaniline

17.5 16.4 15.9 16.9

73.2 68.6 66.5 70.7

HP MS

1986MEO/ELS

HP MS

1986MEO/ELS

RHC–aniline RHZN-methylaniline N,N-dimethy laniline N,N-diethylaniline

16.7 14.2

69.9 59.4

13.3

55.6

(azulene)C–aniline

14.0

58.6

HP MS

1987ELS/MEO

BC–B, BZmesitylene BHC–B 1-CH3-naphthaleneC–B

(1) 17.2 (2) 12.4 (3) 13.9

72.0 51.9 58.2

HP MS

(1) 1978MEO/HAM (2) 1980MEO (3) 1987ELS/MEO

BC–B, BZnaphthalene BHC–B (biphenylene)C–B (biphenyleneH)C–B

17.8 14.1 12.6 13.6

74.5 59.0 52.7 56.9

HP MS

1980MEO

BC–B, BZazulene

16.3

68.2

HP MS

1980MEO

BC–B, BZ1-CH3naphthalene

18.8

78.7

HP MS

1987ELS/MEO (continued)

7366—CHAPTER 24—6/2/2007—13:26—JEBA—15380—XML MODEL B – pp. 1087–1161

1134

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.2 (continued) BDEs in Positive Carbon-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

BC–B, BZfluorene BHC–B

16.5 14.4

69.0 60.2

HP MS

1980MEO

BC–B, BZbiphenylene BHC–B

16.0 13.6

66.9 56.9

HP MS

1980MEO

BiphenyleneC–azulene

15.9

66.5

HP MS

1980MEO

BC–B, BZacenaphthene 17.0 BHC–B 14.8

71.1 61.9

HP MS

1980MEO

BiphenyleneC–B, BZacenaphthene BC–B BHC–B

14.2

59.4

HP MS

1980MEO

17.0 14.8

71.1 61.9

AzuleneC–B, BZbiphenyl BiphenyleneC–B

13.5

56.5

HP MS

1980MEO

13.4

56.1

(biphenylene)C– fluorene

13.3

55.6

HP MS

1987ELS/MEO

AzuleneC–B, BZfluorene BiphenyleneC–B BC–B BHC–B

14.6

61.1

HP MS

1980MEO

13.3 16.5 14.4

55.6 69.0 60.2

BC–B, BZ1,2,3,4,5,6,7,8- 16.5 octahydro-anthracene BHC–B 14.2

69.0

HP MS

1980MEO

59.4

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

BC–B, BZanthracene BHC–B

1135

16.4 16.0

68.6 66.9

HP MS

1980MEO

BC–B, BZphenanthrene 17.8 BHC–B 15.7

74.5 65.7

HP MS

1980MEO

BC–B, BZocthracene BHC–B

16.5 14.2

69.0 59.4

HP MS

1980MEO

BC–B, BZpyrene BHC–B

19.1 16.5

79.9 69.0

HP MS

1980MEO

BC–B, BZchrysene BHC–B

18.2 17.8

76.1 74.5

HP MS

1980MEO

BC–B, BZperylene BHC–B

19.7 19.1

82.4 79.9

HP MS

1980MEO

BC–B, BZ1,12benzoperylene BHC–B

21.6

90.4

HP MS

1980MEO

21.4

89.5

BC–B, BZcoronene

23.8

99.6

HP MS

1980MEO

BC–B, BZphenalenyl

9.5

39.7

ESR

2004SMA/ZAI

BC–B, BZC60

8.58G1.84

35.89G7.72

MS

2002BRA/MAL

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

1136

Comprehensive Handbook of Chemical Bond Energies

24.1.3 Negative carbon-ion clusters/complexes Table 24.1.3 BDEs in Negative Carbon-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

195.5 194 187.2G2.5 188.7G0.2

818.2 812 783.2G10.5 789.6G1.0

(1) Derived (2) Derived (3) Derived (4) Derived from EA in ref.

(1) (2) (3) (4)

150 168 150 155 143 166 138 164

628 704 627 647 598 695 579 685

Derived

1990PAR

CK–H

(1) 110G7 (2) 80.3G0.5

460G29 336.1G2.1

(1) Derived (2) Derived from EA in ref.

(1) 1974GUR/KAR (2) 1996NIST

C6 HK 3 –H

81.1

339

Derived

1992GRA

CK–N

(1) 239G1.5 (2) 239.2G1.0

1000G6.3 (1) Derived 1000.8G4.2 (2) Derived from EA in ref.

(1) 1974GUR/KAR (2) 1996NIST

CK–B

133.3G6.9

558G29

Derived from EA in ref.

1996NIST

C6 HK 5 –H

60.9

255

Derived

1992GRA

CK–C

CK(C)x–C xZ1 2 3 4 5 6 7 8

(1) (2) (3) (4)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

References 1979HUB/HER 1990PAR 1991ERV/LIN 1996NIST

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

H

H

H

H H

at ortho C–H bond meta C–H bond para C–H bond

(1) (2) (2) (2)

89.1 90.1G3.1 98.8G3.1 105.4G2.9

1137

373 377G13.0 413G13.0 441G12.1

(1) Derived (2) FA TQ

(1) 1992GRA (2) 1996WEN/HU

CK 60 –F CK 70 –F C60FK–F

92.7 94.4 86.3

388 395 361

Derived

1997BOL/PON

CK–Mo

117.4G3.8

491G16

Derived from EA in ref.

1996NIST

(h5-C5H5)K–Co –Co(CO)

38.7G2.9 57.1G4.5

162G12 239G19

CID

1999SUN/SQU

CClK 3 –HCl

38.6

162

Derived

1971YAM/KEB

CK–CO

76.3G4.6

319G19.3

Derived

1996ZEN/PER

C6 HK 5 –CO

44

184

Derived

1998WEN/HU

CH$K 2 –CO2

61.7G2.7

258G11.3

FA-TQ

1994WEN/SQU

CHK 3 –CO2

(1) 59.1G2.5 (2) 57.2G1.4

247G10.5 239G5.8

(1) FA-TQ (2) Photodetach.

(1) 1994WEN/SQU (2) 2004LU/CON

CHCK–H2O

16.2

67.8

HP MS

1988MEO

c-C5 HK 5 ðH2 OÞx –H2 O xZ0 1

11.0 10.0

46.0 41.8

HP MS

1988MEO (continued)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

1138

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.3 (continued) BDEs in Negative Carbon-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

CFK 3 ðCF4 Þx –CF4 xZ0 1 2 3 N

(1) (1) (1) (1) (2)

c-C5 HK 5 ðLÞx –L, LZCD3CN xZ0 1 2

15.5 13.1 !10.2

HCCK–CH3OH HCCK–CD3OH

3.6 3.4 3.4 w3.4 w2.8

kJ/mol 15.1 14.2 14.2 w14 w12

Methods (reference in parentheses)

References

(1) HP MS

(1) 1995HIR/NAS

(2) Extrapolate

(2) This volume

64.9 54.8 !42.7

HP MS

1988MEO

(1) 21.6 (2) 21.4

90.4 89.5

FT-ICR

(1) 1999CHA/BRA (2) 2000CHA/BRA

(CH3)3CCK–CH3OH

20.8

87.0

FT-ICR

1999CHA/BRA

c-C5 HK 5 –CH3 OH

13.2

55.2

HP MS

1988MEO

C6H5CCK–CH3OH

(1) 13.3 (2) 21.5

55.6 90.0

(1) ICR (2) FT-ICR

(1) 1984CAL/ROZ (2) 1999CHA/BRA

4-CH3-C6H4CCK–CH3OH

21.6

90.4

FT-ICR

1999CHA/BRA

C6 HK 5 –SiF4 –SiHF3

66.0G2.5 54.9G2.3

276G10.5 230G9.6

FA MS

2003KRO/LAR

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1139

HCCK–CH3O

69.8

292

Derived

1998SCH/BLA

CHK 2 –CH2 CO

77.0

322

Derived

1998SCH/BLA

c-C5 HK 5 –CF3 CH2 OH

20.6

86.2

HP MS

1988MEO

c-C5 HK 5 ðLÞx –L, LZCH3COCH3 xZ0 1

13.5 9.8

56.5 41.0

HP MS

1988MEO

C6 HK 5 –CH3 OSiF3

60.9G3.5

255G14.6

FA MS

2003KRO/LAR

C6H5CCK–nC3H7OH

15.4

64.4

ICR

1984CAL/ROZ

c-C5 HK 5 –tC4 H9 OH

17.0

71.1

HP MS

1988MEO

C6H5CCK–nC5H11OH

17.1

71.5

ICR

1984CAL/ROZ

c-C5 HK 5 –c-C5 H6

!8.6

!36

HP MS

1988MEO

C6 FK 6 –C6 F6

(1) 10.4G1 (2) 9.4G4.6

43.5G4 39.3G19.2

(1) HP MS (2) PES

(1) 1990HIR/MIZ (2) 1993NAK/TAG

c-C5 HK 5 –C6 H5 CH2 OH

20.6

86.2

HP MS

1988MEO

C6H5CCK–C6H5OH –p-CH3-C6H4OH

19.5 22.3

81.6 93.3

HP MS

1984CAL/ROZ

(B)K(B)x–B, BZnaphthalene xZ0

6.7

28.0

PES

2002SON/HAN (continued)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

1140

Comprehensive Handbook of Chemical Bond Energies

Table 24.1.3 (continued) BDEs in Negative Carbon-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment 1 2 3 (An)K(An)x–An, AnZanthracene xZ4 5 6

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

3.9 4.6 3.2

16.4 19.3 13.5

2.8 0.9 0.9

11.6 3.9 3.9

PES

References

2003SON/LEE

24.2 Silicon and the ion clusters/complexes 24.2.1 Silicon clusters/complexes Table 24.2.1 BDEs in Silicon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Si(crystal)–Si

w30

w125

EPR

1965WAT/COR

Si(100, surf.)–Si

15.5G1.8 (phys)

64.7G7.7

STM

1991MO/KLE

Si(100, surf.)–Si

30G7

125G29

STM

1995SWA/SCH

Si(100, 2!1, surf.)–Si

22.4G2.8 (phys)

93.6G11.6

STM

1995PEA/BOR

Si(100, surf.)–Si

107

448

Review

1995SEE/ALL

Si(111, surf.)–Si

(1) w4.6 (phys) w19.3 (2) 17.1G4.6 71.4G19.3

(1) HEED (2) STM

(1) 1993NAK/ICH (2) 1993VOI/ZIN

Methods (reference in parentheses)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

References

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1141

Si(111, surf.)–Si

(1) w30 (2) 32

w125 135

(1) RHEED (2) REM

(1) 1987ICH/DOI (2) 1990LAT/ASE

Si(111, 7!7, surf.)–Si

18.0 (phys)

75.3

STM

2002UCH/WAT

Si(111, 7!7, surf.)–Si

(1) 25.4 (2) 30G4.6

106 125GG19

(1) LEED (2) REM

(1) 1974BED (2) 1990LAT/ASE

O2Si(crystal)–Si

175G23

733G96

RBS

1995JAO/BEJ

Si(111, surf.)Ge–Si

w11.5

w48.2

HEED

1993NAK/ICH

Si(100, surf.)–Ge

(1) 17.5G1.6 (phys) (2) 19.4

73.3G6.8

EM/Scattering

(1) 1987ALL/FEL(b)

Si(100, surf.)–Ge

98

410

Si(111, surf.)–Ge

81.0

(2) 1990ALL/STO

Review

1995SEE/ALL

11.1G0.9 (phys) 46.3G3.9

EM/Scattering

1987ALL/FEL(b)

Si(100, surf.)–Sn

23G4.6 (phys)

96G19

EM/Scattering

1987ALL/FEL(b)

Si(100, surf.)–Sn

101.3

424

Review

1995SEE/ALL

Si(111, surf.)–Sn

7.4G0.9 (phys)

30.9G3.9

EM/Scattering

1987ALL/FEL(b)

Si(111, surf.)–Sn

82.9

347

Review

1995SEE/ALL

Si(111, surf.)–Pb

27.7 (phys)

116

STM

1995HIB/OGI (continued)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

1142

Comprehensive Handbook of Chemical Bond Energies

Table 24.2.1 (continued) BDEs in Silicon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Si(111, surf.)–Pb

42

176

Review

1995SEE/ALL

Si(111, 3!1, surf.)–Li

18.4

77.2

NMR

2001KLE/FIC

SiO2(crystal)–Na

42.7

179

TPD

2000YAK/MAD

Si(100, 2!1, surf.)–K

56

234

TDS

1990TAN/TAK

Si(100, surf.)–Cs

10.8G1.2 (phys)

45.3G4.8

SEI

1994MIL/AZI

Si(100, surf.)–Cs

w46

w193

SEI

1994MIL/AZI

Si(111, surf.)–Al

16 (phys)

67

SEM

1978NES/ZRA

Si(111, surf.)–Al

70

293

Review

1995SEE/ALL

Si(100, surf.)–Ga

17.5 (phys)

73.2

EM/Scattering

1987ALL/FEL

Si(100, surf.)–Ga

66.2G1.8

277G7.5

LIF

1987CAR/LEO

Si(111, surf.)–Ga

11.5 (phys)

48.1

EM/Scattering

1987ALL/FEL

Si(112, surf.)–Ga

101.5G6.9

425G29

AES

1994JUN/PRO

Methods (reference in parentheses)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

References

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1143

Si(111, 7!7, surf.)–In

16.7G1.2 (phys)

69.7G4.8

PACT

1992KRA/DET

Si(111, surf.)–In

59

247

Mol. beam

1974NGU

Si(111, 7!7, surf.)–In

44.5G2.3

186G9.6

PACT

1992KRA/DET

Si(crystal)–Cu

14.5G2.1

60.8G8.8

Photoluminescence

1999NAK/IWA

Si(crystal)Cu–Cu

23.5G1.6

98.4G6.7

TDS

1998IST/HIE

Si(100, surf.)–Ag

33.4G3.7 (phys)

140G15

SEM

1984HAN/FUT

Si(100, 2!1, surf.)–Ag

w83

w347

Calorimetry

2001STA/RAN

Si(111, surf.)–Ag

(1) 16.1G2.8 (phys) (2) 9.2G1.2

67.5G11.6

SEM

(1) 1984HAN/FUT

Si(111, surf.)–Ag

56.5G1.2

236G4.8

AES

1991RAY/HAR

Si(100, surf.)–Sb2

27.7G2.3 (phys)

116G9.6

STM

1993MO

Si(100, surf.)–Sb2

80

335

Review

1995SEE/ALL

Si(100, surf.)–He

(1) 0.3 (2) 0.2

1.1 0.7

Scattering

(1) 1980CAR/BEC (2) 1986SAK/CAR

Si–Ar

1.40

5.86

Spectroscopy

2002TAO/TES

38.6G4.8

(2) 1992RAY/DOU

(continued)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

1144

Comprehensive Handbook of Chemical Bond Energies

Table 24.2.1 (continued) BDEs in Silicon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Si(CH3)2F2–Ar

0.66, at 0 K

2.75

Spectroscopy

2005GIU/OTT

Si(amorp. surf.)–H Polymeric Internal voids In bulk

72.4 73.6 75.9

303.0 307.8 317.4

DSC

2006ROU/FAR

Si(surf.)–H

(1) 57.7G4.6 (2) 53.0G2.3

241G19.3 221.9G9.6

(1) Ion beam (2) Raman

(1) 1993MYE/FOL (2) 2005MA/HUA

Si(polycs. surf.)–H

70–80

293–335

Review

1987FRE

Si(at SiO2–Si interface)–H 80.7

338

Hot-carrier

2000CHE/LEE

Si(at SiO2, amorphous)–H (1) 100G2.2 (2) 99.7–100.6

418G9 417–421

(1) EPR (2) IR

(1) 1990BOB/RAD (2) 2003BRA/NES

a-Si(nanoparticles)–H

74.9

313

Calorimetry

2002FAR/DAS

Si(100, 2!1, surf.)–H

(1) 51.2G4.6 (2) 73.1

214G19.3 306

(2) STM (2) Equilibrium

(1) 1999LIN/CHE (2) 2001RAS/HOF

Si(111, 7!7, surf.)–H

34.6G4.6 (phys)

145G19.3

SHG

1991REI/HOF(b)

Si(111, 7!7, surf.)–H

(1) 55.3 (2) 69.4

232 290

(1) TDP (2) Equilibrium

(1) 1991REI/HOF (2) 2001RAS/HOF

Methods (reference in parentheses)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

References

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1145

n-GaAs(solid)Si–H

27.7G2.3

115.8G9.6

Kinetics

1991ROO/JOH

Si(surf.)–D

(1) 61.6G2.3 (2) 57.4

257.6G9.6 240.2

Equilibrium

(1) 1993WAM/MYE (2) 1997WAM/MYE

Si(100, surf.)–H2

18.0 (phys)

75.3

SHG

1996HAN/HAL

Si(100, surf.)–H2

(1) (2) (3) (4) (5)

47 45G2 49G3 57.2G2 39.2G3.5

197 188G8.4 205G12.6 239G8.4 164G14.5

(1) (2) (3) (4) (5)

LITD LITD TPD TPD Kinetics

(1) (2) (3) (4) (5)

1989SIN/SHE 1990SIN/SHE 1994MIC/LIE 1995GRE/ARM 1999RAS/HOF

Si(100, 2!1, surf.)–H2

(1) (2) (3) (4) (5)

57.2G2.3 57 57.2G2.6 49G3 42.2G4.6

239G9.6 239 239.3G10.9 205G12.6 176.6G19.3

(1) (2) (3) (4) (5)

Desorption TPD LITD Kinetics Equilibrium

(1) (2) (3) (4) (5)

1992HOF/LI 1993FLO/JON 1994OKA/WIS 1995GRE/LIE 2001RAS/HOF

Si(111, surf.)–H2

34.6

145

SHG

1996HAN/HAL

Si(111, 7!7, surf.)–H2

20.1 (phys)

84.0

LEED

1995BRA/HOF

Si(111, 7!7, surf.)–H2

(1) 39–44 (2) 35.1G3.5

163–184 147G14.5

(1) STM (2) Equilibrium

(1) 1998LO/HWA (2) 2001RAS/HOF

Si(100, surf.)–D2

(1) 47 (2) 45G2

197 188.3G8.4

LITD

(1) 1989SIN/SHE (2) 1990SIN/SHE

Si(polycr. surf.)–O2

205

858

Calorimetry

1960BRE/HAY(b)

Si(111, 7!7, surf.)–O2

36.9G4.6

154G19.3

STM

1999HIL/KRA (continued)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

1146

Comprehensive Handbook of Chemical Bond Energies

Table 24.2.1 (continued) BDEs in Silicon Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Si(100, 2!1, surf.)–SiH

65

272

FT-IR

1988GUP/COL

Si(100, 2!1, surf.)–SiH2

43

180

FT-IR

1988GUP/COL

Si(111, surf.)–CaF2

41.5G4.6

174G19.3

STM

2002WOL

Si(100, 2!1, surf.)–NH3

11.2

47

TPD

1989DRE/TAY

Si(111, surf.)–CH3

124.5

521

PES

2005HUN/FRI

Si(100, surf.)–SiH3

2 (phys)

8

SIMS/TPD

1990GAT/GRE(b)

Si(111, 7!7, surf.)–SiH4

4 (phys)

16.7

SIMS/TPD

1990GAT/GRE

Si(111, surf.)–SiH4

(1) 20G5 (2) 36G6 (3) 28.8

84G21 151G25 121

(1) HEED (2) MS (3) Review

(1) 1972HEN/HEL (2) 1974FAR (3) 2001RAU

Si(100, 2!1, surf.)–C2H2

w46

192

TPD

1992TAY/WAL

Si(100, 2!1, surf.)–C2H4

41.5

174

Combined

2001FIN/HUB

Si(110, surf.)–CH2CHBr

6.5

27.3

Spectroscopy

2004NAG/MUK

Si(100, surf.)–C6H6

(1) 28 (2) 27.7

117 115.8

(1) TDS (2) TPD

(1) 1991TAG/FUG (2) 2001FIN/MEN

Methods (reference in parentheses)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

References

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1147

Si(111, 7!7, surf.)–C6H6

w9.2 (phys)

w38.6

TDS/STM

1998BRO/MOF

Si(111, 7!7, surf.)–C6H6

21.8

91.2

TDS

1995WOL/MOF

SiO2(surf.)–C6H6

10.5

44

NMR

1972BOD/HAU

Si(111, 7!7, surf.)–C6H5Cl 23.3G0.2

97.5G1.0

EELS

2000CAO/DEN

Si(surf.)–2-Cl–C6H4OH

3.6G1

15G4

FT-IR

2005ALD/DEL

Me3Si–Re(CO)5

71.5G2.3

299G9.6

Derived

1975BUR/STO

SiCl4–2,2 0 -bypyridine

40.6G1.7

170G7

IR/MS

2004DAV/SEV

24.2.2 Silicon-ion clusters/complexes Table 24.2.2 BDEs in Silicon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

SiC–Au –Pd –Pt

42G12 57G12 126G12

175G50 237G50 525G50

Derived from IP in ref.

1996NIST

SiC–B

(1) 58G13

243G54

(1) Derived

(1) 1974GUR/KAR

(2) 83.8G3.6

351G15

(2) Derived from IP in ref.

(2) 1996NIST

(1) (2) (3) (4)

377 315G3 316G4 316.6G2.1

(1) (2) (3) (4)

(1) (2) (3) (4)

SiC–H

90.0 75.3G0.7 75.4G0.9 75.7G0.5

Methods (reference in parentheses)

PD Spectrom. Ion reactions Derived from IP in ref.

References

1981WAL 1980CAR/COP 1984ELK/ARM 1996NIST (continued)

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Table 24.2.2 (continued) BDEs in Silicon-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

PhSiHC 2 –H

38

159

Ion reactions

1993NAG/MUR

SiC(F)x–F xZ0 1 2 3

163.5G1.3 74.3G1.6 145.7G1.3 21.3G1.5

684.1G5.4 310.9G6.7 609.6G5.4 89.1G6.3

CID

1993FIS/KIC

(1) (2) (2) (2) (2)

591.0G0.6 510 192 485 58.6

(1) Spectroscopy (2) Derived

(1) 1998FAN/LIU (2) 1999KNE/LER

SiC(Cl)x–Cl xZ0 1 2 3

141.2G0.1 122 46 116 14

Methods (reference in parentheses)

References

SiC(CH3)2Cl–Cl

47.7G0.9

199.7G3.9

UV PI

1995SHE/QI(b)

SiC(CH3)3–Cl

42.7G0.5

178.5G1.9

UV PI

1996CHE/SHE

SiC–Br

(1) 102G10 (2) 66G23

427G42 276G96

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

14.2G0.3 4.8G0.3 !1.5

59.4G1.3 20.1G1.3 !6.3

HP MS

1997HIR/KAT(b)

(1) 114G3 (2) 114.1G3.2

477G13 478G13.4

SiCH3(H2)x–H2 xZ0 1 2

SiC–O

SiC–S –Te

(1) 1974GUR/KAR (2) 1996NIST

(3) 133.5G2.8

(1) Derived (2) Derived from IP in ref. 558.5G11.6 (3) Spectroscopy

92.6G1.4 83G12

387.5G6.0 347G50

1996NIST

Derived from IP in ref.

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(3) 2002RED/AHA

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1149

SiC–P

65G12

272G50

Derived from IP in ref.

1996NIST

SiC–C

(1) 80G12 (2) 87G12

335G50 365G50

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

SiC–Si

(1) 90G13 (2) 79.9G4.6

377G54 334G19

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

SiHC 3 ðCOÞx –CO xZ0 1 2 3 4 5 6 7 8 9 10 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

R151 46.4 12.1 11.7 11.7 11.7 11.3 11.3 11.3 7.1 7.1 w7.5

(1) HP MS

(1) 1997HIR/KAT

(2) Extrapolate

(2) This volume

SiFC 3 ðCOÞx –CO xZ0 1

41.6G0.3 15.2G0.3

174.1G1.3 63.6G1.3

HP MS

2000HIR/NAS

(CH3)3SiC–H2O

30.1G1.9

125.9G7.9

HP MS

1986WOJ/STO

(CH3)3SiC–NH3

46.5

194.6

HP MS

1990LI/STO

SiC(CH3)(Cl)2–CH3

14.5G0.7

60.8G2.9

UV PI

1995SHE/QI(b)

SiC(CH3)2(Cl)–CH3

9.9G0.5

41.5G1.9

UV PI

1996CHE/SHE

SiC(CH3)x–CH3 xZ0

98.9G1.4

413.9G5.8

CID

1996LIN/DUN

R36 11.1 2.9 2.8 2.8 2.8 2.7 2.7 2.7 1.7 1.7 w1.8

(continued)

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Table 24.2.2 (continued) BDEs in Silicon-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

29.3G11.5 122.7G6.5 15.9G1.4

123G48 513G27 66.6G5.8

SiC(CH4)x–CH4 xZ0 1 2

R35 9.0G0.3 3.3G0.3

R146 37.7G1.3 13.8G1.3

HP MS

1999HIR/NAS

SiC(SiF4)x–SiF4 xZ1 2

9.5G0.3 w5

39.7G1.3 w21

HP MS

1999HIR/NAS

SiFC(SiF4)x–SiF4 xZ0 1 2

12.4G0.3 9.0G0.3 w6

51.9G1.3 37.7G1.3 w25

HP MS

1999HIR/NAS

SiFC 2 –SiF4

25.7G0.3

107.5G1.3

HP MS

1999HIR/NAS

SiFC 3 ðSiF4 Þx –SiF4 xZ0 1 2

R35 10 w5

R146 42 w21

HP MS

1999HIR/NAS

SiF3 OHC 2 ðSiF4 Þx –SiF4 xZ0 1 2

9.6G0.3 7.7G0.3 w5

40.2G1.3 32.2G1.3 w21

HP MS

1999HIR/NAS

SiF3 OHC 2 ðSiF4 Þx –SiF4 xZ0 1

9.6G0.3 7.7G0.3

40.2G1.3 32.2G1.3

HP MS

2000HIR/NAS

SiF4HC–SiF4

18.9G0.3

79.1G1.3

HP MS

2000HIR/NAS

1 2 3

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References

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

BC–BH, BHZMe2SiH2 Me3SiH tBuSiH3 (Et)2SiH2 Et(Me)2SiH (Et)2MeSiH i-Pr(Me)2SiH (Et)3SiH t-Bu(Me)2SiH

1151

30.2 27.8 31.1 31.6 28.4 31.1 31.7 29.6 32.2

126.4 116.3 130.1 132.2 118.8 130.1 132.6 123.8 134.7

CID

2000HOP/SAU

Me3SiC–Me4Si

(1) 22.3 (2) 21.5

93.3 90.0

(1) HP MS (2) CID

(1) 1987WOJ/LI (2) 2000HOP/SAU

Et3SiC–Et4Si ðMeÞ5 SiC 2 –ðMeÞ6 Si2

27.3 24.1

114.2 100.8

CID

2000HOP/SAU

Et3SiC–Et

16.4G1.6

68.5G6.8

FT-ICR

1996LIN/DUN(b)

(CH3)3SiC–CH2CH2 –CH2CHCH3 –trans-2-butene –isobutene –2-methyl-2butene –2,3-dimethyl2-butene –cyclohexene –styrene

23.6G0.3 30.6G0.4 30.9G0.6 36.5G1.1 38.2G0.5

98.7G1.3 128.0G1.7 129.3G2.5 152.7G4.6 159.8G2.1

HP MS

1989LI/STO

37.9G0.5

158.6G2.1

32.9G1.0 36.6G0.7

137.7G4.2 153.1G2.9

(CH3)3SiC–1-hexene –1-hexyne –2-hexyne –phenylace tylene

38.2 25.9 28.8 28.2

159.8 108.4 120.5 118.0

HP MS

1996ZHA/STO

(CH3)3SiC–CH3OH –C2H5OH –n-C3H7OH –i-C3H7OH –n-C4H9OH –n-C5H11OH

39.2 42.0 43.3 43.9 44.2 44.7

164.0 175.7 181.2 183.7 184.9 187.0

HP MS

1986WOJ/STO

(CH3)3SiC–(CH3)2O –CH3OC6H5

41.8 41.6

175 174

ICR

1991LIN/RID (continued)

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Table 24.2.2 (continued) BDEs in Silicon-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

(CH3)3SiC–(CH3)2CO

(1) 45.0 (2) 44.9

188.3 188

(1) HP MS (2) ICR

(1) 1986WOJ/STO (2) 1991LIN/RID

(CH3)3SiC–(C2H5)2O

44.2

184.9

HP MS

1986WOJ/STO

(CH3)3SiC–cyclohexanone 47.6

199

ICR

1991LIN/RID

(CH3)3SiC–furan (CH3)3SiC–2-methyfuran (CH3)3SiC–2,5methylfuran

38.0 41.1 43.0

159 172 180

ICR

1991LIN/RID

48.7 49.4 50.3 49.9 50.4 48.8

203.8 206.7 210.5 208.8 210.9 204.2

HP MS

1986WOJ/STO

(CH3)3SiC– C6H5COOC2H5

50.8

212.5

HP MS

1986WOJ/STO

(CH3)3SiC–C6H6 –CH3C6H5

(1) (1) (2) (2)

100.0 111.3 118.8 131.0

HP MS

(1) 1986WOJ/STO

(CH3)3SiC–CH3COOR RZC2H5 n-C3H7 i-C3H7 n-C4H9 n-C6H13 C6H5

–CD3C6D5

23.9 26.6 28.4 31.3

References

(2) 1991STO/STO

(CH3)3SiC–1,2-Me2-C6H4 –1,3-Me2-C6H4 –1,4-Me2-C6H4 –1,3,5-Me3-C6H3

29.1 29.0 28.2 31.0

121.8 121.3 118.0 129.7

HP MS

1986WOJ/STO

(CH3)3SiC–CH3NH2 –CH3CH2NH2

55.4 57.4

231.8 240.2

HP MS

1990LI/STO

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BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

–CH3CH2CH2 CH2NH2 – (CH3)2NH –CH3CH2 CH(CH3)NH –(CH3)3CNH

59.5

248.9

60.0 57.9

251.0 242.3

58.0

242.7

SiK–H

(1) 69.8G0.5 (2) 67.5G0.5

292.2G2.0 282.5G2.1

SiK–Si

(2) 92.8G1.0

388.4G4.2

1153

(1) PES (2) Derived from EA in ref.

(1) 1975KAS/HER (2) 1996NIST

24.3 Germanium clusters/complexes 24.3.1 Germanium clusters/complexes Table 24.3.1 BDEs in Germanium Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ge(111, 2!8, surf.)–Ge

O32 (phys)

O134

STM

1994HWA/THE

Ge(111, surf.)–Ge

89

372

Review

1995SEE/ALL

Ge(111, surf.)–Ag

10.4 (phys)

43.5

SEM

1994VEN/PER

Ge(111, surf.)–Ag

56

234

Review

1995SEE/ALL

Ge(111, surf.)–In

41

172

TPD

1994SUN/SEE

Ge(111, surf.)–Pb

12.5G0.7

52.1G2.9

STM

1992GAN/THE

Ge(100, surf)–He

0.14, at 0 K

0.60

AES

1987LAM/TRE (continued)

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Table 24.3.1 (continued) BDEs in Germanium Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ge–Ar

!1.3

!5.4

Spectroscopy

2003TAO/DAG

Ge(111, 2!8, surf)–Kr –Xe

5.6, at 0 K 6.4

23.6 26.7

TFD

1988PAC/WEB

Ge(111, surf.)–H

61

255

Review

1979TOY/SOM

Ge(polycs. surf.)–H2

16.6

69.5

Review

1964HAY/TRA

Ge(surf.)–H2

43.8G4.6

183G19.3

FT IR

1995MYE/STE

Ge(100, 2!1, surf.)–H2

40G2

167.4G8.4

TPD-LID

1995LEW/SEG

Ge(111, surf.)–H2

18.5G2.3 (phys) 77.4G9.6

Review

1979TOY/SOM

Ge(polycr. surf.)–O2

132

552

Calorimetry

1960BRE/HAY(b)

Ge(111, surf.)–O2

64.6G11.5

270G48

Review

1979TOY/SOM

Ge(polycr. surf.)–CO

O26

O109

TD

1966KLE/MOL

Ge(100, surf.)–NH3 Ge(113, surf.)–NH3

17.9–32.3 17.9

75–135 75

Isosteric

2002RAN/JOS

Ge(100, 2!1, surf.)–C2H2

30.0 (a state) 32.3 (b state)

125 135

TPD

2002KIM/MAE

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BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1155

Ge(100, 2!1, surf.)–C2H4

25.4

106

Combined

2001FIN/HUB

Ge(100, 2!1, surf.)–C6H6

11.5

48.2

TPD

2001FIN/MEN

Me3Ge–Co(CO)4 Me3Ge–Re(CO)5

73.8G2.3 73.8G2.3

308.7G9.6 308.7G9.6

Derived

1975BUR/STO

24.3.2 Germanium-ion clusters/complexes Table 24.3.2 BDEs in Germanium-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

GeC–Ge

(1) 65G8 (2) 67.1 (3) 65.5G2.4

272G34 280.8 274G10

(1) Derived (2) Review (3) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996SMI/YAT (3) 1996NIST

GeC–C

(1) 53G15 (2) 53.5G7.4

222G63 224G31

(1) 1974GUR/KAR (2) 1996NIST

(1) 64G11 (2) 64G5

268G46 268G21

(1) Derived (2) Derived from IP in ref.

GeC–H

90G20

377G84

Derived

1974GUR/KAR

GeC–F

(1) 130G6 (2) 135G5

544G25 565G21

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

GeC–Cl –Br

113G12 95G10

473G50 398G42

Derived

1974GUR/KAR

GeC–O

(1) 106G10 (2) 82G5

444G42 344G21

Derived

(1) 1974GUR/KAR (2) 2004LAV/BLA

–Si

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 24.3.2 (continued) BDEs in Germanium-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment) GeC–S

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

68G5

283G21

55.9G2.4

234G10

(1) 46G11 (2) 53.3G4.6

R3GeC–H2O RZCH3 n-C3H7 C4H9

Methods (reference in parentheses)

References

Derived from IP in ref.

1996NIST

193G46 223G19

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

28.6G0.5 23.4G1.3 20.6G1.2

119.7G2.1 97.9G5.4 86.2G5.0

HP MS

1987STO/WYT

(C2H5)3GeC(H2O)x–H2O xZ0 1

24.9G0.5 18.4

104.2G2.1 77.0

HP MS

1987STO/WYT

GeK–Ge

81.7G2.4

342G10

PES

1995ARN/XU

–Se

GeC–Te

24.4 Tin clusters/complexes 24.4.1 Tin clusters/complexes Table 24.4.1 BDEs in Tin Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Cl2Sn–SnCl2

25.5G1.5

106.8G6.2

MS

2005HIL/ROS

Me3Sn–SnMe3

61.6

257.7

MS

1971LAP/PED

Me3Sn–Co(CO)4 Me3Sn–Re(CO)5

64.6G2.3 85.3G2.3

270G9.6 357G9.6

Derived

1975BUR/STO

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BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1157

Sn–Ar

!1.2

!5.1

Spectroscopy

2004TAO/DAG

SnO2(110, surf.)–H2CO

28

117

Re-anal.

2001MAD/IDR

Cl4Sn–CH3CHCHCHO –CH3CHCHC(O)OCH3 –CH3C(CH3)CHCHO –CH3CHCHCN

12.2G0.4 6.1G0.3 12.1G0.2 5.6G0.2

51.0G1.7 25.5G1.3 50.6G0.8 23.4G0.8

Calorimetry

1982CHI/MUL

(CO)5Mn–SnMe3 –SnPh3 –SnMe2Cl

47.0 48.2 51.7

197 202 216

MS

1978SPA

(h-C5H5)(CO)2Fe–SnMe3 –SnPh3 –SnCl3

53.0 59.5 70.6

222 249 295

MS

1978SPA

24.4.2 Tin-ion clusters/complexes Table 24.4.2 BDEs in Tin-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated fragment)

kcal/mol

kJ/mol

SnC–Sn

46.1

193

Derived

1996SMI/YAT

SnC–Cu

44G23

184G96

Derived from IP in ref.

1996NIST

SnC–F

(1) 112G12 (2) 87.1G6.9

469G50 364G29

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

(1) 80G12

335G50

–Br

Methods (reference in parentheses)

References

(continued)

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

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Comprehensive Handbook of Chemical Bond Energies

Table 24.4.2 (continued) BDEs in Tin-Ion Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment) SnC–O

SnC–S

–Se –Te

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 53G15 (2) 67.2G2.4

222G63 281G10

(3) 75.1

314

(1) 55G12 (2) 57.3G4.6

230G50 240G19

(1) (2) (1) (2)

167G50 174G6.3 151G50 168.7G8.4

40G12 41.6G1.5 36G12 40.3G2.0

Methods (reference in parentheses)

References

(1) Derived (2) Derived from IP in ref. (3) Derived

(1) 1974GUR/KAR (2) 1996NIST

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

(3) 2004LAV/BLA

(CH3)3SnC–NH3 –CH3CN –CH3NH2 –C2H5NH2 –N(CH3)3 –N(C2H5)3 –NH(n-C4H9)2 –N(n-C4H9)3

36.9 37.5 42.1 44.1 45.6 45.7 48.8 48.0

154 157 176 185 191 191 204 201

HP MS

1984STO/SPL

(CH3)3SnC–H2O –CH3OH –C2H5OH –C3H7OH –n-C4H9OH –t-C4H9OH –n-C6H13OH

25.7 32.6 34.8 35.5 36.5 36.6 37.5

108 136 146 149 153 153 157

HP MS

1984STO/SPL

(CH3)3SnC–(CH3)2CO –(C2H5)2CO –CH3C(O) OCH3 –CH3C(O) C2H5

37.4 39.5 38.4

157 165 161

HP MS

1984STO/SPL

39.3

164

7366—CHAPTER 24—6/2/2007—13:27—JEBA—15380—XML MODEL B – pp. 1087–1161

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

–CH3C(O) OC2H5 –CH3C(O) O-n-C3H7 –CH3C(O) O-n-C4H9

1159

40.2

168

40.2

168

41.7

175

(CH3)3SnC–C3H7SH

34.2

143

HP MS

1984STO/SPL

(CH3)3SnC–o-xylene –mesitylene

29.9 32.0

125 134

HP MS

1984STO/SPL

SnK–Sn

64.4G0.4

269.4G1.6

PES

1992HO/POL

SnK–Pb

43.7G1.0

182.9G4.2

Combined

2005GIG/MEL

24.5 Lead clusters/complexes Table 24.5 BDEs in Lead Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Pb(110, surf.)–Pb

15.0 (phys)

62.7

HAS

1996HOF/TOE

Pb(polycs. surf.)–H

26–27

109–113

Electrochemical

1970KRI

Pb(100, surf.)–O2

55

230

Review

1979TOY/SOM

PbC–Pb

(1) 40.1 (2) 51.1G6.9

167.7 214G29

(1) Review (2) Derived from IP in ref.

(1) 1996SMI/YAT (2) 1996NIST (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 24.5 (continued) BDEs in Lead Clusters/Complexes

The broken bonds (boldfaceZ dissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

PbC–F

(1) 82G15 (2) 83G7.6

343G63 347G32

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

PbC–Cl –Br

68G15 62G15

285G63 260G63

Derived

1974GUR/KAR

PbC–O

(1) 52G12 (2) 59.1G2.0

218G50 247G8.4

(1) 1974GUR/KAR (2) 2000BRE/BRE

(3) 53.2

223

(1) Derived (2) Derived from IP in ref. (3) Derived

(1) 55G15 (2) 70G12

230G63 293G50

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 2000BRE/BRE

(1) (2) (1) (2)

47G15 40.5G1.5 39G15 39G12

197G63 169.4G6.3 163G63 165G50

PbC(HC 2 O)x–H2O xZ0 1 2 3 4 5 6 7 N

(1) (1) (1) (1) (1) (1) (1) (1) (2)

22.4 16.9 12.2 10.8 10.0 9.6 9.4 9.2 w10.5

93.7 70.7 51.0 45.2 41.8 40.2 39.3 38.5 w44

(1) HP MS

(1) 1972TAN/CAS

(2) Extrapolate

(2) This volume

PbC(NH3)x–NH3 xZ0 1 2 3

28.3G0.2 19.2G0.1 13.0G0.1 10.7G0.2

HP MS

1989GLE/GUO

PbC–S

–Se –Te

118.4G0.8 80.3G0.4 54.4G0.4 44.8G0.8

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(3) 2004LAV/BLA

BDEs in the C-, Si-, Ge-, Sn-, Pb-Clusters and Complexes

1161

PbC–CH2I

R103

R431

LI

1996SCH/HEI

PbC(CH3OH)x–CH3OH xZ0 1

23.3G0.2 17.2G0.3

97.5G0.8 72.0G1.3

HP MS

1990GUO/CAS

PbC(CH3NH2)x–CH3NH2 xZ0 1

35.4G0.3 19.1G0.2

148.1G1.3 79.9G0.8

HP MS

1990GUO/CAS

PbC–C6H6

26.2G0.4

110G2

HP MS

1990GUO/CAS

PbK–Pb

(1) 43.8G0.7 (2) 32.5

183.3G2.9 135.9

(1) PES (2) Review

(1) 1992HO/POL (2) 1996SMI/YAT

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chapter twenty-five

BDEs in the N-, P-, As-, Sb-, Bi-clusters and complexes 25.1 Nitrogen and the ion clusters/complexes 25.1.1 Nitrogen clusters/complexes Table 25.1.1 BDEs in Nitrogen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

N2–He

0.06, at 0 K

C6H5NH2–He

kJ/mol 0.23

Methods (reference in parentheses)

References

Scattering

1987BEN/CAS

w0.29G0.14, 0 K w1.2G0.6

R2PI

1984BER/LAW

Pyridazine–Ne

w0.2, at 0 K

w0.8

Spectroscopy

2000CAM/MEL

Pyridine–Ne

0.3, at 0 K

1.2

Spectroscopy

1998MAR/CAM

Pyrimidine–Ne

0.3, at 0 K

1.3

Spectroscopy

1999CAM/FAV

Carbazole–Ne

!0.61, at 0 K

!2.57

SEP-R2PI

1995DRO/BUR

N2–Ar

w0.3, at 0 K

w1.3

Review

1976BLA/WEWI

NO–Ar

(1) 0.27, at 0 K (2) 0.25 (3) 0.25 (4) 0.257

1.15 1.06 1.05 1.077

(1) Mol. Beam (2) MPI (3) R2PI (4) REMPI

(1) 1984CAS/LAG (2) 1989MIL (3) 1994TSU/SHI (4) 2004PAR/CHA

(continued)

1163

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Table 25.1.1 (continued) BDEs in Nitrogen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

s-Tetrazine–Ar

O1.1, at 0 K

O4.6

LIF

1983BRU/KEN

Pyrrole–Ar

0.79, at 0 K

3.33

Spectroscopy

1995BET/BET

Pyrazole–Ar

0.8, at 0 K

3.4

Spectroscopy

1998CAM/FAV

Imidazole–Ar

0.9, at 0 K

3.7

Spectroscopy

1998CAM/MEL

Indole–Ar

(1) !1.5, at 0 K (2) 1.29G0.04

!6.3 5.39G0.18

(1) PI (2) MATI

(1) 1991OUT/BIC (2) 1998BRA/GRE

1-Methylindole–Ar

1.29–1.86, 0 K

5.4–7.8

PI

1993OUT/DEM

Carbazole–Ar

1.52, at 0 K

6.35

SEP-R2PI

1995DRO/BUR

Aniline–Ar

(1) 1.29, at 0 K (2) 1.18G0.08

5.38 4.95G0.33

(1) Spectroscopy (2) IR

(1) 1993HIN/BER (2) 1999PIE/HEL

Pyridine–Ar

(1) w0.66, at 0 K w2.78 (2) 0.74 3.10

Spectroscopy

(1) 1989KLO/EMI (2) 1995BET/BET

Pyrimidine–Ar

1.06, at 0 K

4.44

Spectroscopy

1985ABE/OHY

C6H5CN–Ar

!0.57, at 0 K

!2.39

LIF

1987KOB/KAJ

BN(surf.)–Ar

(1) 2.1 (2) 2.0 (3) 2.1 (4) 2.1G0.1

9.0 8.3 8.7 8.7G0.5

(1) Adsorption (2) Adsorption (3) Virial anal. (4) Review

(1) 1958ROS/PUL (2) 1962PIE (3) 1979LEV/RYB (4) 1991VID/IHM

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BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1165

N2–Kr

w0.27

w1.13

Mol. beam

1972TUL/LEE

ON–Kr

(1) 0.29, at 0 K (2) 0.31

1.21 1.32

(1) MPI (2) R2PI

(1) 1989MIL (2) 1996BUS/DYK

Carbazole–Kr

1.97, at 0 K

8.23

SEP-R2PI

1995DRO/BUR

Benzonitrile–Kr

!0.57, at 0 K

!2.39

LIF

1987KOB/KAJ

Pyridine–Kr

w0.92, at 0 K

w3.85

Spectroscopy

1989KLO/EMI

BN(surf.)–Kr

(1) 2.6 (2) 2.5

10.9 10.5

(1) Virial anal. (2) Review

(1) 1979LEV/RYB (2) 1991VID/IHM

N–Xe

6.4

26.9

Spectroscopy

1963HER/HER

ON–Xe

0.35, at 0 K

1.47

MPI

1989MIL

Carbazole–Xe

2.55, at 0 K

10.66

SEP-R2PI

1995DRO/BUR

BN(surf.)–Xe

(1) 3.3 (2) 3.4

13.7 14.2

(1) Virial anal. (2) Review

(1) 1979LEV/RYB (2) 1991VID/IHM

N2–Ga

(1) 3.6 (2) 4.5

15.2 19

(1) LIF (2) Raman/ UV/Vis

(1) 1999GRE/HAN (2) 2005HIM/HEB

Cysteine(crystal)–Au

23.8

99.4

PES

2005BEE/GAR

Carbazole–CO

2.05, at 0 K

8.57

SEP-R2PI

1995BUR/DRO(b)

Pyrrole–CO

0.84, at 0 K

3.50

Spectroscopy

1995BET/BET

(continued)

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Table 25.1.1 (continued) BDEs in Nitrogen Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

N2–N2

(1) w0.19 (2) 1.57G0.05

w0.8 6.57G0.21

(1) Review (2) TPD

(1) 1976BLA/WEWI (2) 2005OBE/BRO

N2–H2

w0.13

0.5

Review

1976BLA/WEWI

CN–H2 –D2

0.11 0.12

0.45 0.50

Spectroscopy

1998CHE/HEA

N2–HF

(1) 1.43, at 0 K (2) 1.14G0.01 (3) 1.57

5.98 4.76G0.02 6.58

(1) Spectroscopy (2) Photofrag. (3) IR

(1) 1993NES/CHI (2) 1994BEM/BOH (3) 1994NES/LIN

N2–DF

%1.56, at 0 K

%6.54

IR

1994NES/LIN

NO–HF

1.28G0.01, at 0 K 5.36G0.07

Photofrag.

1992SHO/CAS

HCN–HF

(1) 6.2 (2) 5.4G0.1 (3) 5.63G0.03

26.1 22.6G0.2 23.57G0.12

(1) Spectroscopy (2) Spectroscopy (3) Photofrag.

(1) 1980LEG/MIL (2) 1987WOF/ELI (3) 1998OUD/MIL

CH3CN–HF HCCCN–HF

6.2G0.1 4.9G0.2

26.1G0.6 20.4G0.7

FT-IR

1987LEG/MIL

ON–NO

2.1 (phys.)

8.7

Pyrolysis

2005PET/AND

N2–CO

1.7

7.1

TPD

2005OBE/BRO

N2–H2O

0.8G0.4

3.2G1.7

CRDS

2005COR/HOD

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BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1167

NH3–H2O

2.92, at 0 K

12.21

Review

1995HIL/FRA

Indole–H2O

(1) 4.67G0.04 (2) 4.84G0.23

19.52G0.18 20.25G0.96

(1) MATI (2) DELFINE

(1) 1998BRA/GRE (2) 2000BRA/MEH

1-Methyl-indole–H2O

4.1G0.1

17.2G0.4

DELFINE

1999MON/DIM

3-Methylindole–H2O

4.49G0.06

18.80G0.24

MATI

2004GEO/NEU

(C6H5)(CHO)NH–H2O

5.65G0.30

23.64G1.25

PES-TOF

2001MON/DIM

L–H2O (air–water interface) LZNH3 CH3NH2 (CH3)2NH (CH3)3N

9.8G1.2 6.7G0.7 8.1G0.7 8.8G0.7

41G5 28G3 34G3 37G3

Combined

2000MME/HIC

NH3–HSH

2.98, at 0 K

12.47

Spectroscopy

1995HIL/FRA

HCN–HCN

(1) 3.80G0.16, 0 K 15.9G0.67 (2) 4.40 18.42

Spectroscopy

(1) 1977MET (2) 1981BUX/CAM

NH3–HCN

2.92, at 0 K

12.21

Review

1995HIL/FRA

NH3–CO2

2.82, at 0 K

11.81

Review

1995HIL/FRA

NH3–SCO

2.81, at 0 K

11.75

Review

1995HIL/FRA

NH3–NO2

2.80, at 0 K

11.72

Review

1995HIL/FRA

NH3–NH3

(1) 4.5, at 0 K (2) 2.8 (3) 4.4

18.8 11.7 18.4

(1) Spectroscopy (2) Spectroscopy (3) Review

(1) 1970LOW (2) 1985NEL/FRA (3) 1988CUR/BLA

(continued)

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Table 25.1.1 (continued) BDEs in Nitrogen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NH4(NH3)x–NH3 xZ0 1 2 3 4 5 6 7 N

(1) 7.8 (1) 2.5 (1) 6.0 (1) 6.9 (1) 5.5 (1) 4.6 (1) 5.1 (1) 4.4 (2) w4.7

32.8 10.6 25.1 28.9 23.2 19.3 21.2 18.3 w20

(1) Photolysis

(1) 2002NON/TAG

(2) Extrapolate

(2) This volume

NH3–SO3

24G1

100.4G4.2

Flow reactor

1997LOV

Pyridine–AlI3

37.3G1.5

155.9G6.4

MS

2002TIM/SUV

C6H5NH2–CH4 4-C2H5-C6H5NH2–CH4

1.37 1.66

5.74 6.94

Spectroscopy

1993HIN/BER

Carbazole–CH4

1.91

8.00

SEP-R2PI

1995BUR/DRO(b)

Indole–CH3OH

5.60G0.37

23.43G1.55

Review

2002MON/DIM(b)

NH3–HCCH

2.81

11.77

Review

1995HIL/FRA

CH3CN–CH3CN

(1) 5.1 (2) 5.00G0.12 (3) 5.2

21.3 20.92G0.50 21.8

(1) PVT (2) TC (3) Review

(1) 1960PRA/CAR (2) 1977REN/BLA (3) 1988CUR/BLA

CH3NH2–CH3OH (CH3)2NH–CH3OH

5.59G0.2 6.19G0.2

23.4G0.8 25.9G0.8

PVT

1974MIL/MIN

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BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1169

(CH3)3N–CH3OH

(1) 5.8G0.7 (2) 7.10G0.2 (3) 6.91G0.2 (4) 3.4G0.6

24.3G2.9 29.7G0.8 28.9G0.8 14.2G2.4

(1) NMR (2) IR (3) PVT (4) FT-MW

(1) 1969CLA/GOV (2) 1970FIL/SWI (3) 1974MIL/MIN (4) 1996TAN/IOA

(C2H5)3NH–CH3OH

7.3

30.5

Vapor density

1976TUC/LIP

(C2H5)3N–CH3OH

(1) 8.2 (2) 7.5G0.5

34.3 31.4G2.1

(1) IR (2) PVT

(1) 1966HIR/KOZ (2) 1974MIL/MIN

(CH3)2NC(O)H–CH3OH

7.6G0.3

31.8G1.3

Derived

2006BIR/HUA

(C2H5)3N–DOCD(CF3)2 (iso-Pr)2EtN–DOCD(CF3)2

6.5 6.4

27.2 26.8

Calorimetry

2003MAI/CAR

(CH3)2NC6H5–DOCD(CF3)2

2.0

8.4

Calorimetry

2003MAI/CAR

3.3

13.8

Calorimetry

2003MAI/CAR

7.4

31.0

Calorimetry

2003MAI/CAR

H3N–(CH3)3Ga

(1) 15.2G1.5 (2) 16.3G0.5

63.6G6.3 68.2G2.1

Equilibrium

(1) 2001PEL/CAR (2) 2005CRE/WAN

H3N–(CH3)3In

15.0G0.6

62.8G2.5

Equilibrium

2005CRE/WAN

N2–C6H6

(1) 0.92G0.07, 0 K 3.85G0.29 (2) 0.87–1.01 3.6–4.2

(1) R2PI (2) Review

(1) 1991ERN/KRA (2) 1995GIL/PAR

NH3–C6H6

1.84G0.12, 0 K

R2PI

2002MON/DIM

O

NCH3

(CH2)2

N

DOCD(CF3)2

DOCD(CF3)2

7.70G0.50

(continued)

7366—CHAPTER 25—6/2/2007—10:13—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1170

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Table 25.1.1 (continued) BDEs in Nitrogen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Indole–C6H6

5.21G0.04, 0 K

21.81G0.18

MATI

1998BRA/GRE

3-Methylindole–C6H6

5.02G0.06, 0 K

20.99G0.24

MATI

2005GEO/NEU

NH3–C6H5Cl

2.9G0.5, at 0 K

12.0G2.2

PI

1994GRO/CHE

N2–1,4–C6H4F2

!0.69, at 0 K

!2.87

Spectroscopy

1995GIL/PAR

N2–C6H5CH3

2.25, at 0 K

9.39

R2PI

2003HU/YAN

NH3–C6H5CH3 N(CH3)3–C6H5CH3

1.6–2.3, at 0 K 3.1G0.6

6.8–9.5 12.9G2.4

LIF

1997KEN/HAA

N2–C6H5OH

1.24G0.06, 0 K

5.19G0.25

MATI

1999HAI/DES

NH3–C6H5OH

O6.1, at 0 K

O25.5

Review

2002MON/DIM(b)

N2–C6H5NH2 N2–4-C2H5-C6H5NH2

1.47, at 0 K 1.80

6.16 7.54

Spectroscopy

1993HIN/BER

N2–pyrimidine

1.29 at 0 K

5.38

Spectroscopy

1985ABE/OHY

Py–Py, PyZpyridine

4.93

20.63

TC

1983CUR/FRU

N2–carbazole

1.79, at 0 K

7.50

SEP-R2PI

1995BUR/DRO(b)

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BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1171

NH3–1-naphthol ND3–1-naphthol

7.66G0.01, at 0 K 32.05G0.04 8.01G0.04 33.51G0.17

SEP-R2PI

1995BUR/DRO

NH3–(1-naphthol)

7.66, at 0 K

32.06

R2PI

1995BUR/DRO

ND3–(1-naphthol)

8.01

33.51

R2PI

1995BUR/DRO

NO–NO

2.03G0.11

8.49G0.5

Dissociation

1991HET/CAS

cis(NO)2–nanotube interior

3.6G0.2, at 0 K

15.1G0.7

IR

2003KON/YAT

B–B, 2-pyridone

4.12

17.23

Combined

2000MUL/TAL

B–B, dimethyl-tetrazine (DMT)

3.67, at 0 K

15.36

Fluorescence

1980BRU/HAY

25.1.2 Positive nitrogen-ion clusters/complexes Table 25.1.2 BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NC 2 –He

0.4

1.7

Near UV

1992BIE/SOL

HNC 2 –He

1.2

5.0

Scattering

1996MEU/NIZ

NC 2 –Ne

1.3

5.5

PD

1991BIE/SOL (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) NC–Ar

NC 2 ðArÞx –Ar xZ0

1 2 3 4 5 6 7 8 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 28.1G10.6 118G44 (2) 49.8G2.3 (3) 43.9 (4) 29G10.6

208.4G9.6 183.8 121G44

(1) (2) (3) (4) (5) (5) (5) (5) (5) (5) (5) (5) (6)

102.5 103.2 109.6 114.8G14.6 R15.9 7.3 7.0 6.6 6.5 6.4 w6.4 w6.4 w6

24.5 24.7 26.2 27.4G3.5 R3.8 1.74 1.68 1.57 1.56 1.54 w1.53 w1.52 w1.5

Methods (reference in parentheses)

References

(1) Ion reactions (2) Photofrag. (3) ICM-MS (4) CID

(2) 1991BRO/LAR (3) 1994NON/MAT (4) 1996HAY/FRE

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

HP MS PD Review KER HP MS

(1) 1987ERV/ARM

1973TEN/COM 1990KIM/BOW 1994HIR/YAM 2002WEI/MAH 1992HIR/MOR

(6) Extrapolate

(6) This volume

NC 2 ðN2 ÞðArÞx –Ar xZ0 1 2

8.4 1.6 1.5

35.1 6.7 6.3

HP MS

1997HIR/FUJ

NC 2 ðN2 Þ2 ðArÞx –Ar xZ0 1

8.2 1.3

34.3 5.4

HP MS

1997HIR/FUJ

NC 2 ðN2 Þ3 ðArÞ–Ar

7.6

31.8

HP MS

1997HIR/FUJ

ONC–Ar

(1) 2.97G0.12 12.45G0.48 (2) 2.7 11.4

R2PI

(1) 1984SAT/ACH (2) 1992TAK

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BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

N2OC–Ar

1173

1.97

8.25

PD

1992BIE/SOL(b)

(1) 8.0 (2) 8.0 (2)O7.4 (2) 1.9–3.6 (2) 1.9–3.6 (2) 1.9–3.6 (2) 1.9–3.6 (2) 1.9–3.6 (2) 1.5–1.9 (2) 1.5–1.9 (2) 1.5–1.9 (2) 1.5–1.9 (2) 15–1.9 (3)w1.5

33.3 33.3 O31.1 7.8–15.2 7.8–15.2 7.8–15.2 7.8–15.2 7.8–15.2 6.2–7.9 6.2–7.9 6.2–7.9 6.2–7.9 6.2–7.9 w6

PD

(1) 1997NIZ/SPI (2) 1999DOP/OLK

(3) Extrapolate

(3) This volume

NHC 3 –Ar

2.7

11.4

IRPD

2002DOP/SOL

NHC 4 –Ar

w2.4

w9.9

IRPD

1997DOP/NIP

C6H5OHC–Ar

1.53G0.01

6.40G0.04

MATI

1999HAI/DES

C6H5CNC–Ar

!1.2

!5.1

Derived

2000KIM

(C6H5NH2)C–Ar, p-bond

1.18G0.08

4.95G0.33

IRPD

2005DOP

(indole)C–Ar, p-bond

1.54G0.03

6.44G0.13

IRPD

1998BRA/GRE

(indole)C–Ar, s-bond

1.92G0.40

8.01G1.67

IRPD

2004SOL/DOB(b)

(imidazole)C–Ar, p-bond (imidazole)C–Ar, s-bond

w1.6 2.1

w6.6 9.0

IRPD

2005AND/SOL

N2HC(Ar)x–Ar xZ0 1 2 3 4 5 6 7 8 9 10 11 N

(continued)

7366—CHAPTER 25—6/2/2007—10:14—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1174

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NC–H

(1) 80.9G0.6 339G2.9 (2) R104.13G R435.67G 0.18 0.77

H2NC–H

(1) 130.4G0.5 545.5G1.9 (1) UV PI (2) 130.12G 544.43G0.10 (2) PFI0.02 PEPICO

(1) 1995QI/SHE (2) 2001SON/QIA

D2NC–D

132.72G0.02

555.28G0.10 PFI-PEPICO

2004QIA/LAU

H3NC–H

123.1

515.1

ICR

1977STA/TAA

(H2NNH2)C–H (MeHNNH2)C–H (Me2NNH2)C–H (Me2NNMe2)C–H (n-PrMeNNMe2)C–H (n-BuMeNNMe2)C–H (Et2NNEt2)C–H

78G3 79G3 74 67 69 72 67

326.4G12.6 330.5G12.6 310 280 289 301 280

Derived

1984MEO/NEL

67

280

Me2NHC–H Me3NC–H Me2EtNC–H MeEt2NC–H Et3NC–H (quinuclidine)C–H

94.5 89.9 90.4 88.9 86.4 92.2

395 376 378 372 362 386

ICR

1977STA/TAA

CH3 CH2 NHC 2 –H

103.2

432

ICR

1977STA/TAA

+

Ion reactions

7366—CHAPTER 25—6/2/2007—10:14—CRCPAG—15381—XML MODEL B – pp. 1163–1241

(1) 1987ERV/ARM (2) 1997MIT/TOS

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1175

FCH2 CH2 NHC 2 –H F2 CHCH2 NHC 2 –H F3 CCH2 NHC 2 –H CF3(CH2)2NHC–H CF3(CH2)3NHC–H CF3 NMeC 2 –H CF3 CH2 NMeC 2 –H

106.6 108.5 110.0 110.0 107.3 90.9 89.3

446 454 460 460 449 380.3 374

(histidne)C–H

110.7G2.3

463.1G9.6

VUV

2006WIL/BEL

NC–F

(1) 120G30 (2) 140G10

502G126 584G42

(1) Derived (2) Der. from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

NC–O

(1) 272.1 (2) 275

1138.4 1150

(1) Spectra (2) Derived

(1) 1979HUB/HER (2) 2003DEA/LI

NC–N

(1) 201.8 (2) 201.69G 0.02

844.3 (1) Derived 843.85G0.10 (2) PI

(1) 1979HUB/HER (2) 2005TAN/HOU

(imidazole)C–Zn

51.6G0.9

216.1G3.9

CID

2004RAN/AMU

(1) (2) (1) (2) (2) (2) (2) (2) (2) (2)

30.1 24.7G0.8 7.5 5.9G0.8 6.7G0.8 10.0G0.8 6.3G0.8 5.0G0.8 5.0G0.8 3.3G0.8

HP MS

(1) 1979HIR/SAL (2) 1998HIR/KAT

N2HC(H2)x–H2 xZ0 1 3 4 5 6 7 8

7.2 5.9G0.2 1.8 1.4G0.2 1.6G0.2 2.4G0.2 1.5G0.2 1.2G0.2 1.2G0.2 0.8G0.2

(continued)

7366—CHAPTER 25—6/2/2007—10:14—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1176

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) ONC(O2)x–O2 xZ0 1 2 3 4

ONC(N2)x–N2 xZ0

1 2 3 4 5 6 7 8 9 N

NC–N2

NC 2 ðN2 Þx –N2 xZ0

1 2 3

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) (2) (1) (1) (1) (1)

3.04 3.4 2.91 2.82 2.44 2.35

12.7 14.2 12.2 11.8 10.2 9.8

Review

(1) 1994HIR/YAM (2) 2000SIE/GRE

(1) (2) (3) (1) (2) (1) (2) (2) (2) (2) (2) (2) (2) (2) (4)

5.20 4.61 5.1 4.3 4.18 3.46 3.81 3.40 3.22 3.01 2.78 2.56 1.89 w1.68 w1.3

21.8 19.3 21.3 18.0 17.5 14.5 15.9 14.2 13.5 12.6 11.6 10.7 7.9 w7.0 w6

(1) Irradiation (2) HP MS (3) Review

(1) 1983SPE/FIT (2) 1994HIR/YAM (3) 2000SIE/GRE

(4) Extrapolate

(4) This volume

(1) 78.4G4.6 (2) 86.2G1.8 (3) 72.6

328.0G19.3 360.8G7.7 303.8

(1) EI (2) CID (3) Review

(1) 1984STE/MAR (2) 1995HAY/FRY (3) 2000SIE/GRE

(1) (2) (3) (4) (5) (3) (3) (3)

102.1 105.2G5.8 107.9G6.3 98.7 102.3G14.6 11.5G0.8 11.3G0.8 10.5G0.8

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

24.4 25.1G1.4 25.8G1.5 23.6 24.4G3.5 2.76G0.2 2.71G0.2 2.52G0.2

MS CID HP MS Review KER

7366—CHAPTER 25—6/2/2007—10:14—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1973TEN/CON 1991SCH/ARM 1994HIR/YAM 2000SIE/GRE 2002WEI/MAH

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

4 5 6 7 8 9 10 N

HNC 2 ðN2 Þx –N2 xZ0 1 2 3 4 5 6 7 8 9 10 N

NC 3 ðN2 Þx –N2 xZ0 1 2 3 4 5 6 7 8 9 10 N

(3) (3) (3) (3) (3) (3) (3) (6)

2.46G0.2 2.27G0.2 2.03G0.2 1.87G0.2 1.77G0.2 1.76G0.2 1.66G0.2 w1.3

10.3G0.8 9.5G0.8 8.5G0.8 7.8G0.8 7.4G0.8 7.4G0.8 6.9G0.8 w6

(1) (2) (1) (3) (1) (3) (1) (3) (1) (3) (3) (3) (3) (3) (3) (3) (4)

16.0 14.5 4.0 3.59 3.8 3.43 3.5 3.29 w3.2 2.95 2.22 1.95 1.93 1.84 1.76 1.72 w1.3

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

4.5G0.3 4.1G0.3 4.1G0.3 3.67G0.3 3.25G0.3 2.44G0.3 2.11G0.3 1.80G0.3 1.58G0.3 1.52G0.3 1.35G0.3 w1.3

1177

Extrapolate

(6) This volume

66.9 60.7 16.7 15.0 15.9 14.4 14.6 13.8 w13.4 12.3 9.3 8.2 8.1 7.7 7.4 7.2 w6

HP MS

(1) 1975MEO/FIE (2) 1979HIR/SAL

(4) Extrapolate

(4) This volume

18.8G1.3 17.2G1.3 17.2G1.3 15.3G1.3 13.6G1.3 10.2G1.3 8.8G1.3 7.5G1.3 6.6G1.3 6.4G1.3 5.6G1.3 w6

(1) HP MS

(1) 1989HIR/YAM(b)

(2) Extrapolate

(2) This volume

(3) 1989HIR/MOR(e)

(continued)

7366—CHAPTER 25—6/2/2007—10:14—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1178

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

O2NC(N2)x–N2 xZ0 1 2 3 4 5 6 7 8 9 10 11 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

H4NC–N2

References

19.2G1.3 18.7G1.3 18.2G1.3 15.6G1.3 13.5G1.3 8.6G1.3 8.1G1.3 7.7G1.3 7.3G1.3 7.2G1.3 6.4G1.3 6.4G1.3 w6

(1) HP MS

(1) 1989HIR/YAM

(2) Extrapolate

(2) This volume

13G5

54G21

Diffusion tube

1987GHE/FIT

C6 H5 NHC 2 –N2 , p-bond C6 H5 NHC 2 –N2 , s-bond

2.00 3.15

8.37 13.16

IRPD

2002SOL/DOP(b)

(indole)C–N2, p-bond (indole)C–N2, s-bond

2.00 4.15

8.37 17.35

IRPD

2004SOL/DOB(b)

(imidazole)C–N2, p-bond

1.7–2.6

7.2–10.8

IRPD

2005AND/SOL

(1) (2) (3) (4) (5) (2) (3) (2) (3) (2)

56.9 57.7 59.4G0.8 57.3 57.9 31.0 53.6G0.8 15.5 15.9G0.8 14.6

(1) PI (2) PI (3) HP MS (4) Review (5) Pyrolysis

(1) (2) (3) (4) (5)

ONC(NO)x–NO xZ0

1 2 3

4.60G0.3 4.46G0.3 4.36G0.3 3.73G0.3 3.23G0.3 2.05G0.3 1.94G0.3 1.84G0.3 1.73G0.3 1.71G0.3 1.53G0.3 1.52G0.3 w1.3

kJ/mol

Methods (reference in parentheses)

13.6 13.8 14.2G0.2 13.7 13.8 7.4 12.8G0.2 3.7 3.8G0.2 3.5

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1977NG/TIE(b) 1981LIN/ONO 1994HIR/YAM 2000SIE/GRE 2005PET/AND

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

(3) (2) (3) (3) (3) (3) (3) (3) (6)

5.7G0.2 2.3 3.5G0.2 4.1G0.2 3.0G0.2 3.7G0.2 2.9G0.2 3.2G0.2 w3.3

23.8G0.8 9.6 14.6G0.8 17.2G0.8 12.6G0.8 15.5G0.8 12.1G0.8 13.4G0.8 w13.8

ONC(CO)x–CO xZ0 1 2 3 4 5 6 7 8 9 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

6.5G0.3 5.6G0.3 5.3G0.3 5.1G0.3 3.9G0.3 3.7G0.3 3.4G0.3 3.3G0.3 2.2G0.3 1.0G0.3 w1.8

27.2G1.3 23.4G1.3 22.2G1.3 21.3G1.3 16.3G1.3 15.5G1.3 14.2G1.3 13.8G1.3 9.2G1.3 4.2G1.3 w7.5

ONC–O3

!13.8

(1) (2) (3) (3) (3) (3) (3) (3) (4)

4 5 6 7 8 9 N

ONC(CO2)x–CO2 xZ0

1 2 3 4 5 N

(L)NCH3–CO2 LZCH3 C2H5

NOC(ON2)x–ON2 xZ0

1179

(6) Extrapolate

(6) This volume

(1) HP MS

(1) 1999HIR/SUG

(2) Extrapolate

(2) This volume

!58

FA

1974FEH

!58 36.0 32.2 31.0 30.1 23.8 21.8 w21 w24

(1) FA (2) HP MS (3) HP MS

(1) 1971DUN/FEH (2) 1988ILL (3) 1994HIR/YAM

(4) Extrapolate

(4) This volume

13.2 11.2

55.2 46.9

HP MS

1978MEO

(1) 7.7 (2) 8.7G0.2

32.2 36.4G0.8

HP MS

(1) 1988ILL (2) 1994HIR/FUJ

!13.8 8.6 7.7 7.4 7.2 5.7 5.2 w5.0 w5.7

(continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1180

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 1 2 3 4 5 6 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(3) Extrapolate

(3) This volume

(1) PI (2) AE (3) HP MS

(1) 1981LIN/NG (2) 1994CAM/AIT (3) 1994HIR/FUJ

(4) Extrapolate

(4) This volume

(2) (2) (2) (2) (2) (2) (3)

7.7G0.2 7.1G0.2 5.9G0.2 5.5G0.2 4.8G0.2 w4.6 w4

32.2G0.8 29.7G0.8 24.7G0.8 23.0G0.8 20.1G0.8 w19 w17

(1) (2) (3) (2) (3) (2) (3) (3) (3) (3) (4)

13.1 14.1 17.4G1.5 5.1 5.7G0.2 2.8 5.6G0.2 4.4G0.2 4.1G0.2 w3.9 w4

54.8 58.9 72.8G6.3 21.2 23.8G0.8 11.6 23.4G0.8 18.4G0.8 19.8G0.8 w16.3 w17

HC(ON2)x–ON2 xZ1 2 3 4 5 6 N

(1) (1) (1) (1) (1) (1) (2)

16.7G1.0 6.4G0.2 5.8G0.2 5.4G0.2 5.0G0.2 w4.8 w4

69.9G4 26.8G0.8 24.3G0.8 22.6G0.8 20.9G0.8 w20 w17

(1) HP MS

(1) 1994HIR/FUJ

(2) Extrapolate

(2) This volume

NHC 4 –NH2

1.2G1.2

5.0G4.8

PIMS

1988TOM

(1) (2) (1) (2) (1)

125.5 109.2 57.7 60.2 49.4

HP MS

(1) 1878MEO(b) (2) 1989MEO/SPE

N2OC(ON2)x–ON2 xZ0

1 2 3 4 5 N

HC(HCN)x–HCN xZ1 2 3

30.0 26.1 13.8 14.4 11.8

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

4 N

(1) 9.2 (3) w6

38.5 w25

HC(HCN)x(H2O)–HCN xZ1 2

18.8 15.6

HC(HCN)(H2O)2–HCN

1181

(3) Extrapolate

(3) This volume

78.7 65.3

HP MS

1989MEO/SPE

16.9

70.7

HP MS

1989MEO/SPE

(H4N)C(HCN)x–HCN xZ0 1 2 3 4 5 N

(1) (1) (1) (1) (1) (1) (2)

21.9 17.4 13.7 11.0 7.9 7.4 w6

91.6 72.8 57.3 46.0 33.1 31.0 w25

(1) HP MS

(1) 1986MEO/SPE

(2) Extrapolate

(2) This volume

(H3N)2HC(HCN)x–HCN xZ0 1 2 3 N

(1) (1) (1) (1) (2)

14.2 12.2 12.8 8.6 w6

59.5 51.0 53.6 36.0 w25

(1) HP MS

(1) 1994DEA/KNU

(2) Extrapolate

(2) This volume

(H3N)3HC(HCN)x–HCN xZ0 1

13.4 11.2

56.1 46.9

HP MS

1994DEA/KNU

(CH3H2)NHC–B, BZHCN ((CH3)3)NHC–B ((C3H7)3)NHC–B

20.8 16.8 13.8

87.0 70.3 57.7

HP MS

1985SPE/MEO

HCNHC–B, BZHCN (HCC)CNHC–B (CD3)CNHC–B

26.1 23.8 22.1

109.2 99.6 92.5

HP MS

1985SPE/MEO

n-C3H7CNC–HCN

20.1

84.1

HP MS

1985SPE/MEO (continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1182

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) ONC(H2O)x–H2O xZ0

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

References

18.5 22.7 16.1 13.5

77.4 95 67.4 56.5

(1) HP MS (2) MS

(1) 1973FRE/HIL (2) 1982BUR/HAY

(1) w21.2

w89

(1) 1975FEH/HOW

(2) 14.8G2.3

61.9G9.6

(1) Electron attach. (2) CID

(2) 1993SUN/SQU

(1) 13.8 (2) 33.0G2.8

57.9 138.0G11.6

(1) PD (2) CID

(1) 1992GRA/KIM (2) 1997BAS/DRE

(HCN)HC(H2O)x–H2O xZ0 1 2

27.4 21.4 17.2

114.6 89.5 72.0

HP MS

1989MEO/SPE

(HCN)2HC(H2O)x–H2O xZ0 1

20.1 16.9

84.1 70.7

HP MS

1989MEO/SPE

(1) (2) (3) (4) (1) (3) (1) (2) (3) (1) (2)

72.4 83.3 86.2G4.2 88.7G18 61.5 72.8G4.2 56.1 51.0 57.3G4.2 51.0 45.2

HP MS

(1) (2) (3) (4)

1 2

O2NC–H2O

(ON2)C–H2O

H4NC(H2O)x–H2O xZ0

1 2

3

(1) (2) (1) (1)

kJ/mol

Methods (reference in parentheses)

17.3 19.9 20.6G1 21.2G4.3 14.7 17.4G1 13.4 12.2 13.7G1 12.2 10.8

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1973PAY/CUN 1984MEO 1986MEO/SPE 1992HON/SUN

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

4

9.7 10.6 9.1 8.4 w10.5

40.6 44.4 38.1 35.1 w44

H4NC(NH3)(H2O)x–H2O xZ0 1 2 N

(1) 12.9 (1) 12.7 (1) 12.2 (2)w10.5

54.0 53.1 51.0 w44

H4NC(NH3)2(H2O)x–H2O xZ0 1

12.4 11.7

H4NC(NH3)3–H2O

5 6 N

(1) (2) (2) (2) (5)

1183

(5) Extrapolate

(5) This volume

(1) HP MS

(1) 1973PAY/CUN

(2) Extrapolate

(2) This volume

51.9 49.0

HP MS

1973PAY/CUN

11.7

49.0

HP MS

1973PAY/CUN

H4NC(NH4I)(H2O)x–H2O xZ0 1 2 3 N

(1) 13.3 (1) 12.2 (1) 10.0 (1) 9.5 (2)w10.5

55.6 51.0 41.8 39.7 w44

MS

2004BLA/PES

(2) Extrapolate

(2) This volume

(H2NCHO)HC(H2O)x–H2O xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

21.2 14.0 11.8 9.7 9.9 w10.5

88.7 58.6 49.4 40.6 41.4 w44

(1) HP MS

(1) 1984MEO(b)

(2) Extrapolate

(2) This volume

(1) (2) (1) (2) (1) (2) (2)

18.8G0.3 16.8 14.6G0.3 14.6 12.4G0.8 12.3 10.3

78.7G1.3 70.3 61.1G1.3 61.1 51.9G3.3 51.5 43.1

HP MS

(1) 1981LAU/KEB (2) 1984MEO(b)

CH3NHC 3 (H2O)x–H2O xZ0 1 2 3

(continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1184

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 4 5 N

(HCCCNH)C–H2O

(CH3CN)HC(H2O)x–H2O xZ0 1 2 3 4 5 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 9.0 (2) 8.5 (3) w10.5

37.7 35.6 w44

(3) Extrapolate

(3) This volume

23.3

97.5

HP MS

1985SPE/MEO

(1) (2) (1) (2) (1) (1) (1) (1) (3)

103.8 92.5G5.9 73.2 62.8 65.3 46.9 43.5 42.3 w44

(1) HP MS (2) CID

(1) 1984MEO(b) (2) 1993HON/SUN

(3) Extrapolate

(3) This volume

24.8 22.1G1.4 17.5 15.0 15.6 11.2 10.4 10.1 w10.5

(C2H5CN)2HC(H2O)x–H2O xZ0 1 2

15.9 15.3 10.3

66.5 64.0 43.1

HP MS

1986DEA/MEO

(CH3NCH)C–H2O (CH3CNCH3)C–H2O

14.8G0.7 10.0G0.8

61.9G2.9 41.8G3.4

HP MS

1997MEO/SIE

CF3CH2NHC 2 (H2O)x–H2O xZ0 1 2

21.1G0.2 17.3G0.2 14.2G0.1

88.3G0.8 72.4G0.8 59.4G0.4

HP MS

1981LAU/KEB

C2H5NHC 3 (H2O)x–H2O xZ0 1 2

17.5G0.4 14.7G0.2 13.2G1.2

73.2G1.7 61.5G0.8 55.2G5.0

HP MS

1981LAU/KEB

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1185

(OH(CH2)2NH3)C(H2O)x –H2O xZ0 1 2 3

15.4 13.4 9.8 8.3

64.4 56.1 41.0 34.7

HP MS

1980MEO/HAM

(OH(CH2)3NH3)C(H2O)x –H2O xZ0 1 2 3

13.3 11.6 9.9 9.9

55.6 48.5 41.4 41.4

HP MS

1980MEO/HAM

(CH3)2NHC 2 (H2O)x–H2O xZ0 1 2 3 4 5 N

(1) (1) (1) (1) (1) (1) (2)

15.0 13.5 11.3 10.5 9.4 w8.4 w10.5

62.8 56.5 47.3 43.9 39.3 w35 w44

(1) HP MS

(1) 1984MEO(b)

(2) Extrapolate

(2) This volume

(1) (2) (1) (1) (1)

15.1 15.6 11.6 10.3 9.9

63.2 65.3 48.5 43.1 41.4

(1) HP MS (2) ES MS

(1) 1980MEO/HAM (2) 1996BLA/KLA

n-C3H7NHC 3 (H2O)x–H2O xZ0 1 2 3

CH3C(O)HCN(CH3)2 (H2O)x–H2O xZ0 1 2

16.5 12.3 9.3

69.0 51.5 38.9

HP MS

1984MEO(c)

(CH3)3NHC(H2O)x–H2O xZ0 1 2 3

14.5 11.4 10.0 w8.4

60.7 47.7 41.8 w35

HP MS

1984MEO(b)

(continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1186

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NC(CH3)4(H2O)x–H2O xZ0 1

9.0 w9.4

37.7 w39.3

HP MS

1985MEO/DEA

(n-C3H7CN)HC–H2O (i–C3H7CN)HC–H2O

19.2 19.2

80.3 80.3

HP MS

1985SPE/MEO

NH2 (CH2 )2 NHC 3 ðH2 OÞx –H2 O xZ0 1 2

14.7 12.0 11.0

61.5 50.2 46.0

HP MS

1980MEO/HAM

NH2 (CH2 )3 NHC 3 ðH2 OÞx –H2 O xZ0 1 2 3

11.4 9.9 10.4 w9.4

47.7 41.4 43.5 w39.3

HP MS

1980MEO/HAM

NH2 (CH2 )4 NHC 3 (H2 O)–H2 O

11.0

46.0

HP MS

1980MEO/HAM

(AcAlaOCH3) HC(H2O)x–H2O xZ0 1 2 AcZCH3CO AlaZNHCH(CH3)CO

13.0 12.4 9.5

54.4 51.9 39.7

HP MS

1984MEO(c)

NC(C2H5)4–H2O

7.0

29.3

HP MS

1985MEO/DEA

((C2H5)3)NHC–B, BZH2O

13.2

55.2

HP MS

1983MEO/SIE

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1187

((nC3H7)3)NHC–B ((nC4H9)3)NHC–B

12.5 13.6

52.3 56.9

CH3 CO2 C2 H4 N(CH3 )3C –H2 O

8.0

33.5

HP MS

1999DEA/MEO

nC6 H13 NHC 3 –H2 O

15.2

63.6

ES MS

1996BLA/KLA

C6H5CNHC–H2O

18.9

79.1

HP MS

1985SPE/MEO

C6H5C(O)HCN(CH3)2–H2O 15.1

63.2

HP MS

1984MEO(c)

(B)HC–H2O BZaziridine acetaldimine azetidine propanimine pyrrolidine butanimine piperidine pentanimine

27.4 4.9 24.0 12.1 6.1 13.6 0.8 14.4

114.7 20.7 100.4 50.8 25.7 56.7 3.3 60.2

Derived

2002BOU/CHO

H3 N(CH2 )5 NH32C ðH2 OÞx –H2 O xZ0 1

w18.6 w18.4

w77.8 w77.0

ES MS

1996BLA/KLA

H3 N(CH2 )6 NH32C ðH2 OÞx –H2 O xZ0 1

17.8 17.3

74.5 72.4

ES MS

1996BLA/KLA

H3 N(CH2 )7 NH32C ðH2 OÞx –H2 O xZ0 1

17.8 17.2

74.5 72.0

ES MS

1996BLA/KLA (continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1188

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

H3 N(CH2 )8 NH32C ðH2 OÞx –H2 O xZ0 1

16.9 16.8

70.7 70.3

ES MS

1996BLA/KLA

H3 N(CH2 )9 NH32C ðH2 OÞx –H2 O xZ0 1

16.5 16.3

69.0 68.2

ES MS

1996BLA/KLA

H3 N(CH2 )10 NH32C ðH2 OÞx –H2 O xZ0 1

16.8 16.8

70.3 70.3

ES MS

1996BLA/KLA

H3 N(CH2 )12 NH32C ðH2 OÞx –H2 O xZ0 1

15.7 15.7

65.7 65.7

ES MS

1996BLA/KLA

(MeN(CH2)2NMe3)2C (H2O)x–H2O xZ0 1

12.7 12.2

53.1 51.0

ES MS

1996BLA/KLA

(Me3N(CH2)3NMe3)2C (H2O)x–H2O xZ0 1

11.0 10.7

46.0 44.8

ES MS

1996BLA/KLA

w10

w42

ES MS

1996BLA/KLA

(Me3N(CH2)4 NMe3)2C–H2O

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

(pyridine)HC(H2O)x–H2O xZ0 1 2

(1) (2) (1) (1)

15.0 16.1 9.6 8.3

1189

62.8 67.4 40.2 34.7

HP MS

(1) 1979DAV/SUN (2) 1983MEO/SIE

(Y-pyridine)C–H2O YZ4–CN 4–CH3 4–(CH3)2N

16.0 14.7 12.0

66.9 61.5 50.2

HP MS

1979DAV/SUN

(Y-pyridine)C–H2O YZ2-i-C3H7 2-t-(C4H9) 2,6-(CH3)2 2,6-(C2H5)2 2,6-(i–C3H7)2 2,6-(t–C4H9)2

14.2 14.2 13.2 13.0 12.8 12.5

59.4 59.4 55.2 54.4 53.6 52.3

HP MS

1983MEO/SIE

(pyrrole)HC–H2O (pyrrole)C–H2O

13.8 11.7

57.7 49.0

HP MS

1987HIR/TAK

(pyrrolidine)HC(H2O)x –H2O xZ0 1

13.7 13.0

57.3 54.4

HP MS

1987HIR/TAK

(Y-aniline)HC–H2O YZH m-F m-Cl m-OH m-CN o-NH2 m-NH2 p-NH2 m-CF3 m-CH3 m-CH3O m-CH3S m-C2H5

15.1 14.8 14.8 12.5 17.3 13.9 9.9 14.7 16.1 13.5 10.4 10.6 13.2

63.2 61.9 61.9 52.3 72.4 58.2 41.4 61.5 67.4 56.5 43.5 44.4 55.2

HP MS

1981LAU/NIS

(continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1190

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

C6H5N(CH3)2HC–H2O

10.9

45.6

HP MS

1986KEE/CAS

(Proline)HC–H2O (Valine)HC–H2O

18.9G1.0 19.3G1.0

79.1G4.2 80.8G4.2

HP MS

1974MEO/FIE

(Indole)C–H2O

(1) 13.7, at 0 K 57.3 (2) 13.7 57.3

(1) MATI (2) IRPD

(1) 1998BRA/GRE (2) 2000UNT/JAN

(3-Methylindole)C–H2O

13.3

55.8

MATI

2004GEO/NEU

(1) (2) (1) (1)

61.9 69.4G3.6 52.7 51.0

(1) HP MS (2) IRPD

(1) 1988MEO(c) (2) 2006AND/SOL

(Imidazolyl)HC (H2O)x–H2O xZ0 1 2

14.8 16.6G0.9 12.6 12.2

(n-C10H21NH3)C (H2O)x–H2O xZ0 1 2 3 4

14.8G0.3 12.1G0.3 9.6G0.3 7.5G0.3 6.7G0.3

61.9G1.3 50.6G1.3 40.2G1.3 31.4G1.3 28.0G1.3

Equilibrium

2003LIU/WYT

(Arginine) HC–H2O (Arginine-OMe) HC–H2O

9.0 9.2

37.7 38.5

Equilibrium

2003WYT/BOW

GlyHC(H2O)x–H2O, GlyZglycine xZ0 1 2

(1) 18.4G2.6 (1) 11.5G2.6 (1) 9.5G2.6

77.2G11.0 48.2G11.0 39.8G11.0

(1) ESI

(1) 2005NON/IWA

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

3 4 5 6 7 8 9 10 11 12 13 14 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

8.3G2.6 9.2G2.0 10.7G1.9 11.1G1.8 11.2G1.7 11.7G1.6 12.0G1.4 11.8G1.0 11.9G1.0 11.9G0.9 11.3G0.8 11.0G1.1 w10.5

34.8G11.0 38.3G8.2 44.7G8.1 46.6G7.7 46.7G7.0 49.1G6.8 50.1G5.7 49.5G4.2 49.8G4.3 49.6G3.7 47.2G3.2 46.1G4.6 w44

TrpHC(H2O)x–H2O, TrpZtryptophan xZ0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

7.4G0.6 7.2G0.6 7.7G0.9 8.7G1.2 9.9G1.5 10.4G1.4 10.5G1.5 11.3G1.3 10.8G0.9 11.0G1.0 11.0G0.9 11.1G0.7 11.1G0.5 10.9G0.2 10.8G0.2 w10.5

31.2G2.5 30.3G2.5 32.4G4.0 36.4G5.0 41.4G6.2 43.3G5.9 44.1G6.3 47.1G5.4 45.3G3.9 45.9G4.2 46.0G4.0 46.6G3.0 46.4G2.1 45.5G1.0 45.1G1.0 w44

TrpGlyHC(H2O)x–H2O, TrpGlyZtryptophanylglicine xZ0 1 2 3 4 5 6 7 8 9 10

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1)

13.4G1.3 11.8G1.3 10.9G0.6 11.5G0.7 11.8G0.9 12.6G1.0 12.6G0.6 12.8G0.2 13.3G0.2 13.4G0.2 13.0G0.2

56.0G5.3 49.3G5.3 45.7G2.7 48.3G2.9 49.3G3.8 52.8G4.1 52.6G2.4 53.7G1.0 55.7G1.0 56.2G1.0 54.3G1.0

1191

(2) Extrapolate

(2) This volume

(1) ESI

(1) 2005NON/IWA

(2) Extrapolate

(2) This volume

(1) ESI

(1) 2005NON/IWA

(continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1192

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 11 12 13 14 N

(Ala–Ala)HC(H2O)x–H2O xZ0 1 2 3 4 Ala–AlaZHO(O)CH (CH3)NH–C(O)CH (NH2)CH3

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

References

(2) Extrapolate

(2) This volume

61.9G1.3 43.9G1.3 37.2G1.3 32.6G1.3 28.5G1.3

Equilibrium

2003LIU/WYT

42.3G1.3 37.2G1.3 32.2G1.3

Equilibrium

2004LIU/WYT(b)

10.6G0.3 8.4G0.3 8.3G0.3 7.2G0.3

44.4G1.3 35.1G1.3 34.7G1.3 30.1G1.3

Equilibrium

2004LIU/WYT(b)

10.4G0.3

43.5G1.3

Equilibrium

2004LIU/WYT(b)

kcal/mol (1) (1) (1) (1) (2)

12.4G0.2 11.9G0.2 11.3G0.2 10.9G0.2 w10.5

14.8G0.3 10.5G0.3 8.9G0.3 7.8G0.3 6.8G0.3

(N3-Ac-Lys) HC(H2O)x– H2O xZ0 10.1G0.3 1 8.9G0.3 2 7.7G0.3 N3-Ac-LysZlysine with acetylated amino group in 3-position (side chain)

(Na-Ac-Lys) HC (H2O)x–H2O xZ0 1 2 3 Na-Ac-LysZlysine with acetylated amino group in a-position

(Na-Ac-Lys-OMe) HC(H2O)x–H2O xZ0

kJ/mol 51.8G1.0 49.9G1.0 47.5G1.0 45.6G1.0 w44

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1 2

1193

7.8G0.3 7.1G0.3

32.6G1.3 29.7G1.3

8.5G0.7 7.4G0.7

35.6G2.9 31.0G2.9

Equilibrium

2004LIU/WYT(b)

6.9G0.7

28.9G2.9

Equilibrium

2004LIU/WYT(b)

(Ac-Ax) HC–H2O xZ4 6 8 20 AcZacetyl, AZalanine

6.9 5.8 4.9 !4.3

28.9 24.3 20.5 !18.0

Equilibrium

2004LIU/WYT(b)

(AAA) HC(H2O)x–H2O xZ0 1 2 3 4 AZalanine

12.3G0.3 11.3G0.3 8.7G0.3 7.1G0.3 7.6G0.3

51.5G1.3 47.3G1.3 36.4G1.3 29.7G1.3 31.8G1.3

Equilibrium

2003LIU/WYT

(AAAAA) HC(H2O)x–H2O xZ0 1 2 3 AZalanine

10.5G0.3 8.5G0.3 9.0G0.3 8.6G0.3

43.9G1.3 35.6G1.3 37.7G1.3 36.0G1.3

Equilibrium

2003LIU/WYT

(RAAAA) HC(H2O)x–H2O xZ0 1 2 3 RZarginine, AZalanine

9.3G0.3 7.8G0.3 7.1G0.3 8.4G0.3

38.9G1.3 32.6G1.3 29.7G1.3 35.1G1.3

Equilibrium

2003LIU/WYT

(Ac-AAKAA) HC(H2O)x– H2O xZ0 1 AcZacetyl, AZalanine, KZlysine

(Ac-AAKAA) HC–H2O, KZlysine

(continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1194

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(AARAA) HC(H2O)x–H2O xZ0 1 RZarginine, AZalanine

10.2G0.3 8.4G0.3

42.7G1.3 35.1G1.3

Equilibrium

2003LIU/WYT

(Ac-AARAA) HC (H2O)x–H2O xZ0 1 AcZacetyl, RZarginine, AZalanine

9.5G0.3 8.1G0.3

39.7G1.3 33.9G1.3

Equilibrium

2003LIU/WYT

9.4G0.3 8.4G0.3 7.6G0.3

39.3G1.3 35.1G1.3 31.8G1.3

Equilibrium

2003LIU/WYT

9.2G0.3 7.8G0.3

38.5G1.3 32.6G1.3

Equilibrium

2003LIU/WYT

11.4 10.8

47.7 45.2

HP MS

1985MEO/SIE

(1) (2) (2) (3)

75.7 96.7 38.5 37.7

(1) PI MS (2) EI

(1) 1977NG/TRE (2) 1982STE/FUT(b)

(3) EI

(3) 1989BRE/TZE

(AARAA-OMe) HC(H2O)x–H2O xZ0 1 2 RZarginine, AZalanine

(AAAAR-OMe) HC(H2O)x–H2O xZ0 1 RZarginine, AZalanine

H4NC–H2S (CH3)H3NC–H2S

H3NC(NH3)x–NH3 xZ0 1

18.1 23.1 9.2 9

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

HC(NH3)x–NH3 xZ1

2

3

4

5

6

7 8 9 10 11 12 13 14 15 16 N

(1) (2) (3) (4) (5) (1) (2) (4) (6) (1) (6) (2) (4) (7) (1) (6) (2) (4) (7) (1) (6) (4) (5) (6) (4) (7) (7) (7) (7) (7) (7) (7) (7) (7) (7) (7) (8)

27 25.4 26.9 26.0 25.6 17 17.3 16.6 16.2 16.5 13.5 14.2 13.7 14 14.5 11.7 11.8 11.7 12 7.5 7.0 7.0 7 6.5 6.5 6 5 5 4 4 5 4 5 4 4 4 w4.7

113.0 106.3 112.5 108.8 107.1 71.1 72.4 69.5 67.8 69.0 56.5 59.4 57.3 58.6 60.7 49.0 49.4 49.0 50 31.4 29.3 29.3 29 27.2 27.2 25 21 21 17 17 21 17 21 17 17 17 w20

1195

(1) (2) (3) (4) (5)

HP MS HP MS HP MS Review HP MS

(1) (2) (3) (4) (5)

1968SEA/KEB 1975TAN/CAS 1991MEO/SIE 1992MEO 1994DEA/KNU

(6) HP MS

(6) 1974ARS/FUT

(7) MKER

(7) 1990WEI/TZE

(8) Extrapolate

(8) This volume

H4NC(H2O)x–NH3 xZ1 2 3

18.4 18.2 17.3

77.0 76.1 72.4

HP MS

1973PAY/CUN

H4NC(NH3)(H2O)x–NH3 xZ1 2

17.1 15.7

71.5 65.7

HP MS

1973PAY/CUN (continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1196

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

H4NC(NH3)2(H2O)–NH3

15.0

62.8

HP MS

1973PAY/CUN

(HCN)xHC(NH3)x–NH3 xZ1 2

18.9 12.9

79.1 54.0

HP MS

1994DEA/KNU

(CH3CN)xHC(NH3)x–NH3 xZ0 1 2 3 4 5 6 7 N

(1) (1) (1) (1) (1) (1) (1) (1) (2)

64.9 56.9 31.0 28.9 25.1 23.0 25.1 23.0 w20

(1) MKER

(1) 1991TZE/WEI

(2) Extrapolate

(2) This volume

H3 N(CH2 )x NHC 3 –NH3 xZ10 12

20.3 19.5

84.9 81.6

MS

2002PES/BLA

(NHC 3 )(CH3 )–NH3 ((CH3 )NHC 2 )(CH3 )–NH3

21.4 20.6

89.5 86.2

HP MS

1973YAM/KEB

((CH3)3)NHC–NH3 ((C2H5)3)NHC–NH3 (C5H5)NHC–NH3

17.3 16.3 17.3

72.4 68.2 72.4

HP MS

1984MEO(b)

(C5H9)O2NC–NH3 (C5H12)O2NC–NH3

20.6 20.9

86.2 87.4

HP MS

1974MEO/FIE(b)

H4NC(MeOCH2)2–NH3

14.0G0.8

58.6G3.4

HP MS

1996MEO/SIE

15.5 13.6 7.4 6.9 6.0 5.5 6.0 5.5 w4.7

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1197

(valine)HC–NH3 (proline)HC–NH3

20.9G1.0 20.6G1.0

87.4G4.2 86.2G4.2

HP MS

1974MEO/FIE

HCNHC–HC(O)H

27.4

114.6

HP MS

1985SPE/MEO

NHC 4 –NCCN

%10.4

%43.5

HP MS

1985SPE/MEO

NHC 4 –CH4

3.6

15.0

HP MS

1972BEN/FIE

CH3 NHC 3 –CH3 F –CH3Cl –CH3Br

11.8 10.7 11.2

49.4 44.8 46.9

HP MS

1984MEO

ONC–CH3Cl

18.5

77.4

FT-ICR

1997CAC/PET

N(CH3 )C 4 –CH3 Cl

6.5

27.2

HP MS

1985MEO/DEA

C6 H5 NHC 3 –CH3 I

9.3

38.9

HP MS

1986KEE/CAS

ONC–CH3OH

(1) 30.2 (2) 23.3

126.4 97.5

(1) PA (2) FT-ICR

(1) 1984LIA/LIB (2) 1997CAC/PET

O2NC–CH3OH

19.2G2.3

80.3G9.6

CID

1993SUN/SQU

MeCNHC(MeOH)(MeCN) –MeOH

13.7

57.3

HP MS

1991ELS/OLA

CH3NCHC–CH3OH

19.0G0.8

79.5G3.4

HP MS

1997MEO/SIE

CH3 NHC 3 –CH3 OH

19.0

79.5

HP MS

1984MEO (continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1198

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(CH3)3NHC(B)x–B, BZCH3OH xZ0 1 2

15.1 11.7 10.5

63.2 49.0 43.9

HP MS

1992ELS/DAL

(CH3)4NC(B)x–B, BZCH3OH xZ0 1

9.8 9.2

41.0 38.5

HP MS

1985MEO/DEA

(indole)C –CH3OH

14.64G0.44

61.25G1.84

Review

2002MON/DIM(b)

56.1 95.0 69.0

HP MS

1985MEO/SIE

(1) (2) (3) (4)

CH3 NHC 3 (CH3 CN)x –CH3 SH xZ0 13.4 1 22.7 2 16.5

HC(B)x–B, BZCH3CN xZ1

2

ONC(B)x–B, BZCH3CN xZ0 1 2 3 4 N

O2NC(B)x–B, BZCH3CN xZ0 1

(1) (2) (3) (4)

30.2 29.8 31.1G2.3 9.3

126.4 124.7 130.1G9.6 38.9

(1) (2) (3) (4)

HP MS HP MS CID HP MS

(1) (2) (2) (2) (2) (2) (3)

26.4G2 26.2G1.1 19.2G1.1 17.7G1.1 14.1G1.1 8.9G0.6 w7.9

110.5G8.4 109.6G4.6 80.3G4.6 74.1G4.6 59.0G4.6 37.2G2.5 w33

(1) FT-ICR (2) HP MS

(1) 1995CAC/PET (2) 2000WIN

(3) Extrapolate

(3) This volume

(1) 24.8G1.2 (1) 16.9G0.9

103.8G5.0 70.7G3.8

(1) HP MS

(1) 2000WIN

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1978MEO(b) 1985SPE/MEO 1993HON/SUN 2000WIN

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

2 3 4 N

H4NC(B)x–B, BZCH3CN xZ0 1 2 3

(1) (1) (1) (2)

15.6G1.1 2.2G1.1 8.8G1.1 w7.9

27.6 21.2 14.2 11.7

CH3 NHC 3 (B)x –B, BZCH3CN xZ0 (1) (2) 1 (1) (2) 2 (1)

24.5 26.2 17.9 18.6 13.4

65.3G4.6 51.0G4.6 36.8G4.6 w33

1199

(2) Extrapolate

(2) This volume

115.5 88.7 59.4 49.0

HP MS

1991LIE/ROM

102.5 109.6 74.9 77.8 56.1

HP MS

(1) 1984MEO (2) 1985MEO/SIE

(CH3)2NC–CH3CN

26.2

109.6

HP MS

1985SPE/MEO

CH3 NHC 3 (CH3 SH)–CH3 CN C6 H5 NHC 3 –CH3 CN

19.9 17.2

83.3 72.0

HP MS

1986KEE/CAS

CH3CNHC–CD3CN

30.2

126.4

HP MS

1997MEO/SIE

(CD3 CN)C 2 –CD3 CN

15.2

63.7

CERMS

2003MAI/FED

H4NC–CH3NC CH3 NHC 3 –CH3 NC (CH3 )2 NHC 2 –CH3 NC (CH3)3NHC–CH3NC CH3NCHC(CH3NC) –CH3NC

24.1G1.7 23.8G0.8 20.6G0.3 19.5G0.8 25.2G1.0

100.7G7.0 99.7G3.2 86.2G1.4 81.6G3.2 105.5G4.0

HP MS

1997MEO/SIE

CH3 NHC 3 –HCðOÞOH

19.0

79.5

HP MS

1984MEO (continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1200

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NHC 4 –HCCCN CD3 NHC 3 –HCCCN HCCCNHC–HCCCN

22.9 24.0 27.4

95.8 100.4 114.6

HP MS

1985SPE/MEO

NHC 4 –CH2 CH2

10

41.8

HP MS

1985DEA/MEO

BHC–B, BZCH2CHCN

30.7

128.4

HP ME

1991MEO/SIE

CH3 NHC 3 –HCðOÞNH2

30.0

125.5

HP MS

1984MEO(c)

(1) (2) (3) (2) (4) (2) (4) (2) (5)

90.8 106.3 112.1G4.2 66.9 80.3 56.1 71.1 32.6 w26

(1) HP MS (2) HP MS (3) VG MS

(1) 1973YAM/KEB (2) 1992MEO (3) 1999NOR/MCM

(4) HP MS

(4) 1982HOL/CAS

(5) Extrapolate

(5) This volume

HC(B)x–B, BZCH3NH2 xZ1

2 3 4 N

21.7 25.4 26.8G1.0 16.0 19.2 13.4 17.0 7.8 w6

NHC 4 –CH3 NH2 (CH3 )2 NHC 2 –CH3 NH2

w32 22.4

w134 93.7

HP MS

1973YAM/KEB

NC(CH3)4–CH3NH2

8.7

36.4

HP MS

1985MEO/DEA

CD3 NHC 3 –CH3 NH2 –CD3NH2

26.9G1.0 27.0G1.0

112.5G4.2 113.0G4.2

MS

1999NOR/MCM

119.7

HP MS

1984MEO(c)

(AcAlaOCH3)HC–CH3NH2 28.6 AcZCH3CO AlaZNHCH(CH3)CO

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

BHC–B, BZHC(O)NH2 CH3(O)NH2 C2H5(O)NH2 neo-C5H11 (O)NH2 HC(O)N(CH3)2 CH3(O)N (CH3)2 C2H5(O)N (CH3)2 neo-C5H11 (O)N(CH3)2

FT-ICR

1997WIT/GRU

104.2 105.4G3.8 81.5G5.4 62.3G4.6 51.9G5.0

(1) FT-ICR (2) HP MS

(1) 1997CAC/PET (2) 1998WIN

22.1G0.9 19.2G1.1 15.5G1.6 12.8G1.3

92.5G3.8 80.3G4.6 64.9G6.7 53.6G5.4

HP MS

1998WIN

(valine)HC–B, BZCH3NO2 19.8G1.5 17.5G1.5 (proline)HC–B

82.8G6.5 73.2G6.5

HP MS

1974MEO/FIE

ONC–C2H5Cl –CH2(CN)2

19.6 19.6

82.0 82.0

FT-ICR

1997CAC/PET

ONC–(CH2)2O

26.9

112.5

FT-ICR

1997CAC/PET

ONC–CH3C(O) H

(1) 41.1 (2) 27.6

172 115.5

(1) ICR (2) FT-ICR

(1) 1981REE/FRE (2) 1997CAC/PET

92.0

HP MS

1984MEO

ONC(B)x–B, BZCH3NO2 xZ0 1 2 3

O2NC(B)x–BZCH3NO2 xZ0 1 2 3

28.8 28.8 25.6 27.0

120.6 120.6 107.1 113.0

26.3 26.5

110.0 111.0

22.8

95.5

20.5

85.9

(1) (2) (2) (2) (2)

1201

24.9 25.2G0.9 19.5G1.3 14.9G1.1 12.4G1.2

(CH3NH2)HC–CH3C(O)OH 22.0

(continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1202

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(AcAlaOCH3)HC –CH3C(O)OH AcZCH3CO AlaZNHCH(CH3)CO

18.1

75.7

CH3C(O)HCN(CH3)2– CH3C(O)OH

18.4

77.0

HP MS

1984MEO(c)

(NH4)C–HO(CH2)xOH xZ2 3 4

28.9G1 33.2G1.2 33.0G1

121G4 139G5 138G4

HP MS

1998STO/CAR

ONC–C2H5OH

35.2

147.3

PA

1984LIA/LIE

CH3NCH3–C2H5OH

21.3

89.1

HP MS

1984MEO

NHC 4 –C2 H5 SH

38.9

162.8

HP MS

1973YAM/KEB

CH3 NHC 3 –C2 H5 SH

(1) 14.6 (2) 15.5

61.1 64.9

HP MS

(1) 1985MEO/SIE (2) 1986KEE/CAS

ONC–C2H5CN

27.6

115.5

FT-ICR

1997CAC/PET

CH3 NHC 3 –C2 H5 CN (C2H5CN)2HC–C2H5CN

24.5 25.2G0.8

102.4 105.4G3.4

HP MS

1997MEO/SIE

CH3 NHC 3 –C2 H5 NC (C2H5NC)2HC–C2H5NC

23.8G0.6 25.2G0.8

99.5G2.7 105.4G3.4

HP MS

1997MEO/SIE

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1203

ONC–C2H5NO2

26.9

112.5

FT-ICR

1997CAC/PET

(C2H5NO2)HC–C2H5NO2

31

129.7

HP MS

1979MEO/HUN

ONC–iso-C3H7Cl

21.4

89.5

FT-ICR

1997CAC/PET

ONC –CH3ONO2 –C2H5ONO2 –iso-C3H7ONO2

20.7 22.7 24.3

86.6 95.0 101.7

FT-ICR

1997CAC/PET

ONC–(CH3)2CO

(1) 46.2 (2) 41.0 (3) 31.1

193 171.5 130.1

(1) ICR (2) Review (3) FT-ICR

(1) 1981REE/FRE (2) 1986KEE/CAS (3) 1997CAC/PET

H4NC(B)x–B, BZ(CH3)2CO xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

118.4G6.3 84.9G2.9 66.1G1.3 54.8G6.2 42.3 w28

(1) HP MS

1996MEO/SIE

(2) Extrapolate

(2) This volume

CH3 NHC 3 –ðCH3 Þ2 CO

24.0

100.4

HP MS

1984MEO

NC(CH3)4(B)x–B, BZ(CH3)2CO xZ0 1 2

14.6 13.0 11.7

61.1 54.4 49.0

HP MS

1985MEO/DEA

NC(C2H5)4–(CH3)2CO

12.4

51.9

HP MS

1985MEO/DEA

CH3NCHC–(CH3)2CO

21.2G1.1

88.7G4.6

HP MS

1997MEO/SIE

MeCO2(CH2)2NCMe3 –Me2CO

13.2G0.3

55.2G1.3

HP MS

1999DEA/MEO

28.3G1.5 20.3G0.7 15.8G0.3 13.1G1.5 10.1 w6.5

(continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1204

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) HC(B)xCH3–B, BZCH3NHCH3 xZ0

1 2 3 4 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

(1) (2) (3) (2) (2) (2) (2) (4)

20.8 24.1 25.7 16.4 9.9 7.9 6.3 w6

kJ/mol

87.0 100.8 107.5 68.6 41.4 33.1 26.4 w25

Methods (reference in parentheses)

References

(1) HP MS (2) HP MS (3) VG MS

(1) 1973YAM/KEB (2) 1992MEO (3) 1999NOR/MCM

(4) Extrapolate

(4) This volume

CD3NCH2CH3 –CH3NHCH3 –CD3NHCH3

25.8 26.0

107.9 108.8

MS

1999NOR/MCM

CH3NCH3–CH3NHCH3 (CH3)3NHC–CH3NHCH3

27.5 20.5

115.1 85.8

HP MS

1973YAM/KEB

ONC–C2H5CHO

(1) 43.3 (2) 38.1

181 159.4

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1986KEE/CAS

ONC–CH3COOCH3

(1) 45.0 (2) 39.8

188 166.5

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1986KEE/CAS

CH3 NHC 3 –CH3 COOCH3

23.5

98.3

HP MS

1984MEO

N(CH3 )C 4 (B)x –B, BZ(CH3)2CO2 xZ0 1

12.1G0.3 9.9G0.4

50.6G1.3 41.4G1.7

HP MS

1999DEA/MEO

HC(B)x–B, BZC2H5NH2 xZ1 2 3

(1) 24.7G1.0 (2) 19.5 (2) 17.3

103.3G4.2 81.6 72.4

(1) VG MS (2) HP MS

(1) 1999NOR/MCM (2) 1974ZIE/WIN

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1205

CD3 CH2 NHC 3 –CH3 CH2 NH2 25.0G1.0 –CD3CH2NH2 25.2G1.0

104.6G4.2 105.4G4.2

MS

1999NOR/MCM

CH3 CD2 NHC 3 –CH3 CH2 NH2 25.3G1.0 –CH3CD2NH2 25.4G1.0

105.9G4.2 106.3G4.2

MS

1999NOR/MCM

BHC–B, BZCH3CONHCH3 29.8

124.7

HP MS

1984MEO(c)

ONC–n-C3H7CN –iso-C3H7CN –tert-C4H9CN

28.0 28.4 29.0

117.2 118.8 121.3

FT-ICR

1997CAC/PET

CH3 NHC 3 –n-C3 H7 CN

28.1

117.6

HP MS

1984MEO

NHC 4 –i-C4 H8

35.1

146.9

HP MS

1991MEO/SIE

BHC–B, BZCH3CH2NHCH3

24.0G1.0

100.4G4.2

MS

1999NOR/MCM

CD3 CH2 NHC 2 CH3 –CH3 CH2 NHCH3 –CD3CH2NHCH3

24.1G1.0

100.8G4.2

MS

1999NOR/MCM

24.2G1.0

101.3G4.2

CH3 CD2 NHC 2 CH3 –CH3 CH2 NHCH3 –CH3CD2NHCH3

24.0G1.0

100.4G4.2

MS

1999NOR/MCM

24.2G1.0

101.3G4.2

CH3 CH2 NHC 2 CD3 –CH3 CH2 NHCH3 –CH3CH2NHCD3

24.0G1.0

100.4G4.2

MS

1999NOR/MCM

24.2G1.0

101.3G4.2

H4NC–H2C(CH3O)2O

29.1G3.6

121.8G15.1

HP MS

1996MEO/SIE

ONC–CH3COC2C2H5

(1) 47.4 (2) 42.2 (3) 32.1

198 176.6 134.3

(1) ICR (2) Review (3) FT-ICR

(1) 1981REE/FRE (2) 1986KEE/CAS (3) 1997CAC/PET (continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1206

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CH3 NHC 3 –CH3 COC2 H5 –CF3COOC2H5

25.2 21.4

105.4 89.5

HP MS

1984MEO

(CH3 )2 NHC 2 –ðCH3 Þ3 N

23.3

97.5

HP MS

1973YAM/KEB

(CH3)4NC–(CH3)3N

9.9

41.4

HP MS

1985MEO/DEA

94.1 100.4 92.0 28.9 !34 27.2 w22

HP MS

(1) 1973YAM/KEB (2) 1991WEI/TZE (2) 1992ELS/DAL

(4) Extrapolate

(4) This volume

BHC(B)x–B, BZN(CH3)3 xZ0

1 2 N

(1) (2) (2) (2) (3) (3) (4)

22.5 24 22.0 6.9 !8 6.5 w5.3

(Me2 N)C 2 –ðMe2 NÞ2 –(EtMeN)2

13.0 15.7

54.4 65.7

HP MS

1987NEL/RUM

BC–B, BZCH3OC(O)CH2NH2

31

130

HP MS

1979MEO/HUN

ONC–n-C3H7CHO

(1) 44.4 (2) 39.2

184 164.0

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1986KEE/CAS

ONC–CH3COOC2H5

(1) 46.7 (2) 41.5 (3) 31.4

195 173.6 131.4

(1) ICR (2) Review (3) FT-ICR

(1) 1981REE/FRE (2) 1986KEE/CAS (3) 1997CAC/PET

(1) 24.5 (1) 16.0

102.5 66.9

(1) HP MS

(1) 1992MEO

HC(B)x–B, BZnC3H7NH2 xZ1 2

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

3 4 5 N

(2) (1) (2) (1) (1) (3)

19.5 14.0 17.1 7.7 7 w7

81.6 58.6 71.5 32.2 29 w29

1207

(2) HP MS

(2) 1982HOL/CAS

(3) Extrapolate

(3) This volume

HC(B)x–B, BZi-C3H7NH2 xZ2 3

19.5 17.1

81.6 71.5

HP MS

1974ZIE/WIN

ONC–n-C3H7NO2 –iso-C3H7NO2 –n-C4H9NO2 –tert-C3H7NO2 –C6H5NO2 –o-CH3-C6H4NO2

27.7 28.2 27.9 29.5 29.7 30.7

115.9 118.0 116.7 123.4 124.3 128.4

FT-ICR

1997CAC/PET

(CH3)3NHC –(N(CH3)2)(CH3)CO

27.2

113.8

HP MS

1984MEO(c)

(CH3)4NC–CH3CON(CH3)2 18.0

75.3

HP MS

1985MEO/DEA

BHC–B, BZCH3CON(CH3)2

28.8G1.2

120.6G4.8

IR radiation

1997PRI/SCH

BHC–B, BZ(N(CH3)2)(CH3)CO

31.3

131.0

HP MS

1984MEO(c)

ONC–(C2H5)2O

(1) 46.5 (2) 41.3

194 172.8

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1986KEE/CAS

CH3 NHC 3 –ðC2 H5 Þ2 O (CH3)3NHC–(C2H5)2O (pyridine)HC–(C2H5)2O c-C6 H11 NHC 3 –ðC2 H5 Þ2 O

22.0 19.5 22.5 21.9

92.0 81.6 94.1 91.6

HP MS

1983MEO

(continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1208

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CH3 NHC 3 –n-C4 H9 OH –t-C4H9OH

23.5 22.9

98.3 95.8

HP MS

NHC 4 –HOCH2 CHCHCH2 OH –HOCH(CH3)(CH3)CHOH

32.3G1.4

135G6

HP MS

1998STO/CAR

34.9G1.4

146G6

30.2

126.4

HP MS

1985SPE/MEO

CH3 NHC 3 –B BZCH3OC2H4OCH3 (CH3)3NHC–B (pyridine)HC–B c-C6 H11 NHC 3 –B

30.1 26.7 25.4 29.4

125.9 111.7 106.3 123.0

HP MS

1983MEO

HC(B)3–B BZC2H4(NH2)2 1,2(NH2)2C3H6 1,3(NH2)2C3H6

17.5G0.5 19.5G0.5 19.7G0.6

73.2G2.1 81.6G2.1 82.4G2.5

HP MS

1973WIN/HER

BHC–B, BZC2H5NHC2H5

23.6G1.0

98.7G4.2

MS

1999NOR/MCM

CD3 CH2 NHC 2 C2 H5 –C2 H5 NHC2 CH5 –CD3CH2NHC2H5

23.7G1.0 23.9G1.0

99.2G4.2 100.0G4.2

MS

1999NOR/MCM

CH3 CD2 NHC 2 C2 H5 –C2 H5 NHC2 H5 –CH3CD2NHC2H5

23.8G1.0 24.0G1.0

99.6G4.2 100.4G4.2

MS

1999NOR/MCM

BHC–B, BZt-C4H9CN

1984MEO

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

ONC–(C2H5)2CO

(1) (2) (3) (4)

CH3 NHC 3 –ðC2 H5 Þ2 CO

201 180 174.1G8 136.8

(1) (2) (3) (4)

25.9

108.4

HP MS

1984MEO

H4NC(B)x–B, BZMeO(CH2)2OMe xZ0 1 2

38G3 23.2G1.3 14.4G1.2

159G12 97.1G5.4 60.3G5.0

HP MS

1996MEO/SIE

CH3 NHC C4 H 9 3 –HCOO-n –CH3COO-n-C3H7

24.5 30.0

102.5 125.5

HP MS

1984MEO

ONC–CH3COO-n-C3H7

(1) 47.2 (2) 42.0

197 175.7

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1986KEE/CAS

ONC–CH3COO-tert-C4H9

33.7

141.0

FT-ICR

1997CAC/PET

(1) 20.1

84.1

HP MS

(1) 1985MEO/DEA

(2) 34.5

144.3

HP MS

(2) 1984MEO

CH3 NHC 3 –CH3 COAlaOCH3 , 40.1 AlaZNHCH(CH3)CO

167.8

HP MS

1984MEO(c)

BHC–B, BZCH3 COAlaOCH3

30.1

125.9

HP MS

1984MEO(b)

C3 H7 Þ! CH3 NHC 3 –ðn ðC2 H5 ÞCO

27.0

113.0

HP MS

1984MEO

N(CH3 )C 4 –B, BZCH3CONHCH2 COOCH3 (pyrimidine)HC–B

48.1 42.9 41.6G2 32.7

1209

ICR Review FT-ICR FT-ICR

(1) (2) (3) (4)

1981REE/FRE 1986KEE/CAS 1996RYZ/KLI 1997CAC/PET

(continued)

7366—CHAPTER 25—6/2/2007—10:15—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1210

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

ONC–CH3CO-iso-C3H7 –CH3CO-tert-C4H9

33.0 33.5

138.1 140.2

FT-ICR

1997CAC/PET

ONC–(iso-C3H7)2CO –(tert-C4H9)2CO

34.0 33.7

142.3 141.0

FT-ICR

1997CAC/PET

ONC–(CH3)(C6H5)2CO –(C6H5)2CO

35.1 38.3

146.9 160.3

FT-ICR

1997CAC/PET

ONC–(C3H5)2CO –(CH2C6H5)2CO

36.5 39.5

152.7 165.3

FT-ICR

1997CAC/PET

CH3NHC 3 –B BZ(n-C3H7)2O (pyridine)HC–B c-C6 H11 NHC 3 –B

24.0 23.5 25.4

100.4 98.3 106.3

HP MS

1984MEO

30.5G0.8

127.6G3.4

HP MS

1996MEO/SIE

31.2 25.5 26.5 28.4 26.2

130.5 106.7 110.9 118.8 109.6

HP MS

1983MEO

(1) 23.9 (2) 20.9G1

100.0 87.4G4

HP MS

(1) 1983MEO/SIE (2) 2003RUS/IBR

BHC(NH3)–B, BZMeOC2 H4OC2H4OMe

CH3 NHC 3 –B, BZCH3O (CH2)3OCH3 N(CH3 )C 4 –B (pyridine)HC–B c-C6 H11 NHC 3 –B (2-F-pyridine)HC–B

BHC–B, BZ(C2H5)3N

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

(CH3)3NHC–B BZCH3(OCH2CH2)2OCH3 (1,2-diazine)HC–B (pyridine)HC–B (2-F-pyridine)HC–B c-C6 H11 NHC 3 –B

1211

32.8 32.4 31.5 34.7 39.7

137.2 135.6 131.8 145.2 166.1

HP MS

1983MEO

ONC–(i-C3H7)2CO

(1) 49.8 (2) 44.6

208 186.6

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1986KEE/CAS

CH3 NHC 3– n-C4 H9 COO-n-C3 H7

30.0

125.5

HP MS

1984MEO

CH3 NHC 3 –ðn-C4 H9 Þ2 O (CH3)4NC–(n-C4H9)2O

(1) 25.0 (2) 12.9

104.6 54.0

HP MS

(1) 1983MEO (2) 1985MEO/DEA

ONC–CH3CO(OCH3)2CH3 –CH3CON(CH3)2 –CH3CON(CH2CH3)2

37.0 39.7 41.6

154.8 166.1 174.1

FT-ICR

1997CAC/PET

34.6

144.8

HP MS

1983MEO

37.0 34.7 43.3

154.8 145.2 181.2

(CH3)3NHC–(n-C6H13)2O

27.2

113.8

HP MS

1984MEO

BHC–B, BZNR3 RZn-C3H7 n-C4H9

22.5 24.4

94.1 102.1

HP MS

1983MEO/SIE

(1) 25.8G0.7 (2) 25.4G1.2

108.1G2.9 106.3G4.8

IR radiation

(1) 1997PRI/SCH (2) 1997PRI/JOC

(CH3)3NHC–B, BZCH3(OCH2CH2)3 OCH3 (1,2-diazine)HC–B (pyridine)HC–B c-C6 H11 NHC 3 –B

BHC–B, BZalanine (Ala)

(continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1212

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) arginine (Arg) lysine (Lys)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(2) 30.7G1.8 (1) 26.5G1.2

128.3G7.7 111.0G4.8

(1) 26.5G1.2

111.0G4.8

(2) 27.7G1.2 (2) 18.4G1.7

116G5 77G7

24.2G1.2 27.7G1.2

101.3G4.8 115.8G4.8

25.4G1.2

106.3G4.8

(glucine)HC -alanine

26.5G1.2

NHC 4 –c-C6 H12 CH3 NHC 3 –c-C6 H12

ONC–C6H6

BHC(B)x–B, BZglucine (Gly) xZ0

Methods (reference in parentheses)

References

(1) IR radiation (2) HP MS

(1) 1997PRI/SCH

IR radiation

1997PRI/JOC

110.9G4.8

IR radiation

1997PRI/SCH

!9 11.6

!37.7 48.5

HP MS

1985DEA/MEO

(1) 46.3 (2) 41.1 (3) 31.3

194 172 131

(1) ICR (2) Review (3) FT-ICR

(1) 1981REE/FRE (2) 1986KEE/CAS (3) 1997CAC/PET

H4NC(B)x–B, BZC6H6 xZ0 1 2

19.3 17.0 14.2

80.8 71.1 59.4

HP MS

1985DEA/MEO

CH3 NHC 3 –C6 H6 (CH3)3NHC–C6H6

18.8 15.9

78.7 66.5

HP MS

1985DEA/MEO

1

BHC–B, BZarginine methyl ester arginine.arginine methyl ester glycine methyl ester

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

(2) 2005RAS/MCM

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1213

(CH3)4NC–C6H6

(1) 9.4 (2) 8.6G0.4

39.3 36.0G1.7

HP MS

(1) 1985MEO/DEA (2) 1999DEA/MEO

(C6H5)(CH3)NHC–C6H6 (C6H5)(CH3)2NC–C6H6 (p-CH3C6H4) (CH3)2NC–C6H6 (aniline)C–C6H6

12.2 9.8 8.9

51.0 41.0 37.2

HP MS

1986KEE/CAS

11.3

47.3

(indole)C–C6H6

13.10G0.03

54.80G0.13

MATI

2000BRA/MEH

ONC–C6H5F

(1) 43.0 (2) 37.8 (3) 28.6

180 158 119.7

(1) ICR (2) Review (3) FT-ICR

(1) 1981REE/FRE (2) 1986KEE/CAS (3) 1997CAC/PET

H4NC–C6H5F

14.4

60.2

HP MS

1985DEA/MEO

(aniline)C–C6H5F

11.8

49.4

HP MS

1986KEE/CAS

H4NC–1,4-C6H4F2

13.0

54.4

HP MS

1985DEA/MEO

(aniline)C–C6F6

11.0

46.0

HP MS

1986KEE/CAS

ONC–C6H5Cl

(1) 43.7 (2) 38.5

183 161

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1986KEE/CAS

(aniline)C–C6H5Cl

12.0

50.2

HP MS

1986KEE/CAS

(aniline)C–C6H5Br

(1) 14.1 (2) 13.6

59.0 56.9

HP MS

(1) 1986KEE/CAS (2) 1987ELS/MEO

(aniline)C–C6H5I

13.6

56.9

HP MS

1986KEE/CAS (continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1214

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

ONC –C6H5CN

(1) 46.3 (2) 41.1 (3) 29.0

194 172 121.3

(1) ICR (2) Review (3) FT-ICR

(1) 1981REE/FRE (2) 1986KEE/CAS (3) 1997CAC/PET

ONC –o-CH3-C6H4CN

29.5

123.4

FT-ICR

1997CAC/PET

CH3 NHC 3 –C6 H5 CN

29.4

123.0

HP MS

1984MEO

(aniline)C–C6H5CN

21.8

91.2

HP MS

1986KEE/CAS

ONC –C6H5C(O)H

48.9

204

ICD

1981REE/FRE

ONC –C6H5NO2

(1) 44.5 (2) 39.3

186 164

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1986KEE/CAS

(aniline)C–C6H5NO2

19.5

81.6

HP MS

1986KEE/CAS

ONC–C6H5CH3

(1) 49.4 (2) 44.2 (3) 34.5

206 185 144.3

(1) ICR (2) Review (3) FT-ICR

(1) 1981REE/FRE (2) 1986KEE/CAS (3) 1997CAC/PET

(CH3)4NC–C6H5CH3

9.5

39.7

HP MS

1985DEA/MEO

(aniline)C–C6H5CH3

14.0

58.6

HP MS

1986KEE/CAS

ONC–C6H5CF3

(1) 40.4 (2) 35

169 146

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1986KEE/CAS

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1215

(aniline)C–C6H5CF3

12.1

50.6

HP MS

1986KEE/CAS

ONC–C6H5C2H5

(1) 49.7 (2) 44.5 (3) 35.3

208 186 147.7

(1) ICR (2) Review (3) FT-ICR

(1) 1981REE/FRE (2) 1986KEE/CAS (3) 1997CAC/PET

(aniline)C–C6H5OCH3

16.8

70.3

HP MS

1986KEE/CAS

CH3 CO2 CH2 CH2 N ðCH3 ÞC 3 –B BZC6H5CH3 3-CH3C6H4OH C6H5OCH3

8.1G0.7 12.8 12.3

33.9G2.9 53.6 51.5

HP MS

1999DEA/MEO

(aniline)C–p-xylene

14.5

60.7

HP MS

1986KEE/CAS

H4NC–B, BZmesitylene

21.8

91.2

HP MS

1985DEA/MEO

(aniline)C–B BZmesitylene

15.3

64.0

HP MS

1986KEE/CAS

ONC–n-C3H7C6H5

(1) 50.3 (2) 45.1

210 188.7

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1996KEE/CAS

ONC–i-C3H7C6H5

(1) 50.3 (2) 45.1

210 188.7

(1) ICR (2) Review

(1) 1981REE/FRE (2) 1996KEE/CAS

(aniline)C–n-C4H9C6H5

14.6

61.1

HP MS

1986KEE/CAS

BHC–B BZC6H5N(CH3)2 p-CH3-C6H4N(CH3)2

10.0 16.2

41.8 67.8

HP MS

1986KEE/CAS

H4NC–B, BZcyclohexane CH3 NHC 3 –B

!9 11.6

!37.7 48.5

HP MS

1985MEO/DEA (continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1216

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(aniline)C–naphthalene –1-CH3-naphthalene –1-bromonaphthalene –acenaphthylene

15.4 15.8 15.8 17.2

64.4 66.1 66.1 72.0

HP MS

1986MEO/ELS

(aniline)C –C6(CH3)6 –acenaphthene –azulene

17.1 18.3 14.3

71.5 76.6 59.8

HP MS

1986KEE/CAS

ONC–B BZpyridine 3-F-pyridine 4-Cl-pyridine 3-CH3-pyridine

40.1 37.3 38.8 41.1

167.8 156.1 162.3 172.0

FT-ICR

1997CAC/PET

(1) (2) (3) (4) (5) (2) (2)

99.2G4.2 110.0 102.9 105.4 105.4G4 52.7 56.9

HP MS

(1) (2) (3) (4) (5)

BHC(B)x–B, BZpyridine xZ0

1 2

23.7G1 26.3 24.6 25.2 25.2G1 12.6 13.6

1979MEO 1982HOL/CAS 1983MEO/SIE 1992MEO 2003RUS/IBR

(C2H5)3NHC–2-F-pyridine

20.8

87.0

HP MS

1984MEO

BHC–B BZ2-CH3–pyridine 2-i-C3H7–pyridine 2-t-C4H9–pyridine

23.0 23.0 23.0

96.2 96.2 96.2

HP MS

1983MEO/SIE

BHC–B BZ2,6-(CH3)2–pyridine 2,6-(C2H5)2–pyridine 2,6-(iC3H7)2–pyridine 2,6-(tC4H9)2–pyridine

23.3 22.8 23.6 w23

97.5 95.4 98.7 w96

HP MS

1983MEO/SIE

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1217

(CH3COGlyOCH3)HC– pyrimidine, GlyZNHCH2CO

28.6

119.7

HP MS

1984MEO(c)

(pyrimidine)HC– CH3COGlyOCH3, GlyZNHCH2CO

34.5

144.3

HP MS

1984MEO(c)

CH3 NHC 3 –pyrrole

18.6

77.8

HP MS

1985DEA/MEO

(B)xHC–B, BZpyrrole xZ0 1

16.8 12.3

70.3 51.5

HP MS

1987HIR/TAK

BC(B)x–B, BZpyrrole xZ0 1

16.5 13.8

69.0 57.7

HP MS

1987HIR/TAK

(B)xHC–B, BZpyrrolidine xZ0 1

22.3 15.3

93.3 64.0

HP MS

1987HIR/TAK

ONC–adenine –cytosine –guanine –thymine

40.3 40.4 40.1 35.6

168.6 169.0 167.8 149.0

Correlation

1997CAC/PET

BHC–B, BZcytosine adenine thymine

38.3G3 30.3G1 30.1G2

160.2G12.6 126.8G4.2 125.9G8.4

HP MS

1979MEO

BHC–B, BZproline

(1) 20.0G2.0 (2) 29

83.7G8.4 121

HP MS

(1) 1974MEO/FIE (2) 1979MEO/HUN

(valine)HC–proline

23.4G2.0

97.9G8.4

HP MS

1974MEO/FIE (continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1218

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.2 (continued) BDEs in Positive Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

prolineHC–B, BZvaline BHC–B

21.0G2.0 20.7G2.0

87.9G8.4 86.6G8.4

HP MS

1974MEO/FIE

BHC–B, BZaniline (C6H5)(CH3)NHC–B (C6H5)(CH3)2NC–B (p-CH3-C6H4)(CH3)2NC–B

17.4 17.4 14.5 13.5

72.8 72.8 60.7 56.5

HP MS

1986KEE/CAS

c-C6 H11 NHC 3 (B)x –B, BZAcAlaNH xZ0 1 AcZCH3CO AlaZNHCH(CH3)CO

37.8 20.4

158.2 85.4

HP MS

1988MEO(c)

(1) 27.7 (2) 25.8G1.8 (1) 21.8

115.9 108.1G7.7 91.2

(1) HP MS (2) IR radiation

(1) 1988MEO(c) (2) 1998JOC/WIL

(C2 H5 )NHC 2 –ImNH ImNHC–ImNH ImNZimidazolyl, N2C3H3

(1) 22.6 (1) 23.7 (2) 25.6G0.9

94.6 99.2 107.1G3.9

(1) HP MS

(1) 1988MEO(c) (2) 1998JOC/WIL

RHC–12-crown-4-ether RZ(CH3)3N 1,2-diazine Pyridine c-C6H11NH2

35.8 37.0 36.1 37.2

149.8 154.8 151.0 155.6

HP MS

1983MEO

RHC–15-crown-5-ether RZ(CH3)3N

(1) 34.9

146.0

HP MS

(1) 1986KEE/CAS

ImNHC(AcAlaNH)x– AcAlaNH xZ0 1 ImNZimidazolyl, N2C3H3 AcZCH3CO AlaZNHCH(CH3)CO

(2) IR radiation

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

Pyridine c-C6H11NH2

RHC–18-crown-6-ether RZ(CH3)3N 1,2-Diazine Pyridine c-C6H11NH2

(betain)HC–betaine –TMG –TMDB –TMDP –DMPA –TBA (DBU)HC–DBU (DBN)HC–DBN TMGZ1,1,3,3-tetramethyl guanidine TMDBZN,N,N 0 ,N 0 tetramethyldiaminobutane TMDPZN,N,N 0 ,N 0 tetramethyldiaminopropane DMPAZN,N-dimethyl4-pyridine-amine TBAZtri-n-butylamine DBUZ1,7-diazobicyclo [5.4.0]-undec-7ene DBNZ1,5-diazobicyclo [4.3.0]non-5-ene

1219

(2) 41.0 (2) 42.3

171.5 177.0

(2) 1983MEO

41G4 42G4 40G4 46G4

171.5G16.7 175.7G16.7 167.4G16.7 192.5G16.7

HP MS

1983MEO

33.4G1.2 30.4G1.6 28.1G0.9 27.0G0.7 27.9G1.2 27.7G1.4 31.1G1.8 32.3G1.8

139.9G4.8 127.4G6.8 117.7G3.9 112.9G2.9 116.7G4.8 115.8G5.8 130.3G7.7 135.1G7.7

IR radiation

1998PRI/JOC

25.1.3 Negative nitrogen-ion clusters/complexes Table 25.1.3 BDEs in Negative Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) NOK(Ar)x–Ar xZ0

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 2.5G0.4 (2) 1.6

10.5G1.7 6.6

Methods (reference in parentheses) (1) Photodet. (2) PES

References (1) 1988BOW/EAT (2) 2002HEN/CLE (continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1220

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.3 (continued) BDEs in Negative Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

1 2 3 4 5 N

(2) (2) (2) (2) (2) (3)

NOK–Kr

2.6

NOK(Xe)x–Xe xZ0 1 2 3 N

(1) (2) (2) (2) (2) (3)

1.5 1.3 1.3 1.3 1.2 w1.5

4.1G0.6 4.2 3.9 3.5 2.8 w3

kJ/mol

Methods (reference in parentheses)

References

6.4 5.6 5.5 5.3 5.0 w6

(3) Extrapolate

(3) This volume

10.7

(2) PES

2002HEN/CLE

17.2G2.5 17.6 16.4 14.5 11.6 w12

(1) Photodet. (2) PES

(1) 1988BOW/EAT (2) 2002HEN/CLE

(3) Extrapolate

(3) This volume

c-C5H4NK–H

104G5

435G21

Derived

1981MCD/CHO

C6H5NK–H

91.3G2

382G8

Derived

1981MCD/CHO

NK–S

92G10

385G42

Derived

1974GUR/KAR

NK–N

182.9

765.1

Derived

1979HUB/HER

NK–C

237.7

994.4

Derived

1979HUB/HER

NK–Si

143.9G3.2

602.1G13.5 PES

2004MEL/SHE

NK–B

171.1G1.8

715.8G7.7

1998ASM/TAY(b)

PES

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1221

NOK(NO)x–NO xZ0 1

(1) 39.2G1.2 (2) 17.8G1.2

164.0G4.8 74.3G4.8

(1) Photodet. (2) PES

(1) 2002LI/CON (2) 1998TSU/SAE

(NO2)K(NO)x–NO xZ0 1

5.3G1.2 8.8G1.2

22.2G4.8 36.7G4.8

Photodetach.

2002LUO/CLE

(1) (2) (3) (1) (3) (4) (3) (4) (3) (4) (3) (4) (4) (4) (5)

w21.3 73.3G9.6 21.3 w25.1 24.6 23.4 21.9 21.3 20.9 18.8 17.6 18.8 18.4 17.6 w17

(1) PES (2) CID (3) PES

(1) 1987COE/SNO (2) 1999TOR/SUL (3) 2002HEN/CLE

(4) HP MS

(4) 1994HIR/FUJ(b)

(5) Extrapolate

(5) This volume

20.9 18.4

PES

1986COE/SNO(b)

90.8 86.6 83.9G6.8 68.6 52.7 45.6 41.0 35.6 31.8 w25

(1) ICR (2) HP MS (3) CID

(1) 1987LAR/MCM(b) (2) 1988MEO/CYB (3) 2006CHA/KRO

(4) Extrapolate

(4) This volume

NOK(N2O)x–N2O xZ0

1

2 3 4 5 6 N

(NO2)K(N2O)x–N2O xZ0 1

CNK(HCN)x–HCN xZ0

1 2 3 4 5 6 N

w5.1 17.5G2.3 5.1 w6.0 5.9 5.6 5.2 5.1 5.0 4.5 4.2 4.5 4.4 4.2 w4

5 4.4

(1) (2) (3) (2) (2) (2) (2) (2) (2) (4)

21.7 20.7 20.1G1.6 16.4 12.6 10.9 9.8 8.5 7.6 w6

(continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1222

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.3 (continued) BDEs in Negative Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CNK(H2O)(HCN)x–HCN xZ1 2

13.2 12.3

55.2 51.5

HP MS

1989MEO/SPE

CNK(H2O)2(HCN)–HCN CNK(H2O)3–HCN

12.6 13.1

52.7 54.8

HP MS

1989MEO/SPE

23.9 ImNK–HCN ImNZimidazolyl, N2C3H3

100.0

HP MS

1988MEO(c)

CNK–CO2

17.3G0.8

72.4G3.3

ICR

1988LAR/SZU

(1) (2) (2) (2) (2) (2) (2) (2) (2) (3)

38.9 30.4G0.8 27.9G0.8 26.5G0.8 25.3G0.8 21.9G0.8 20.7G0.8 18.5G0.8 17.5G0.8 w24

(1) HP MS (2) HP MS

(1) 1980KEE/LEE (2) 1992HIR/YAM

(3) Extrapolate

(3) This volume

(NO2)K(CO2)x–CO2 xZ0 1 2 3 4 5 6 7 N

9.3 7.27G0.2 6.68G0.2 6.34G0.2 6.04G0.2 5.23G0.2 4.94G0.2 4.42G0.2 4.19G0.2 w5.7

(pyridine)K(CO2)2–CO2

3.9

16.4

PES

2000HAN/CHU

CNK–SO2

21.7

90.8

ICR

1988LAR/SZU

(1) (2) (1) (3) (1)

108.3 101.5 37.7 41.0 27.6

(1) HP MS (2) FA

(1) 1980KEE/LEE (2) 1984BOH/FAH

(3) HP MS

(3) 1983WLO/LUC

(NO2)K(SO2)x–SO2 xZ0 1 2

25.9 24.2 9.0 9.8 6.6

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

(NO3)K(SO2)x–SO2 xZ0 1 CNK(H2O)x–H2O xZ0

1 2 3 N

1223

(1) 18.2 (2) 17.2 (1) 8.8

76.1 71.9 36.8

(1) HP MS (2) FA

(1) 1983WLO//LUC (2) 1984BOH/FAH

(1) (2) (3) (4) (4) (4) (5)

57.7 61.1 53.1G3.3 49 44.8 41.0 w44

(1) (2) (3) (4)

(1) 1971PAY/YAM (2) 1988MEO (3) 1988LAR/SZU (4) 1989MEO/SPE

13.8 14.6 12.7G0.8 11.7 10.7 9.8 w10.5

HP MS HP MS Derived HP ME

(5) Extrapolate

(5) This volume

CN–(HCN)(H2O)x–H2O xZ0 1

12.4 9.5

51.9 39.7

HP MS

1989MEO/SPE

CN–(HCN)2(H2O)x–H2O xZ0 1

7.7 8.9

32.2 37.2

HP MS

1989MEO/SPE

CNK(HCN)3–H2O

9.4

39.3

HP MS

1989MEO/SPE

(1) 16.6 (2) 16.6 (1) 15.7

69.5 69.5 65.6

PES

(1) 1990EAT/ARN (2) 2002HEN/CLE

NK 3 ðH2 OÞx –H2 O xZ0 1 2

10.6 10.1 10.6

44.4 42.5 44.4

PES

2004YAN/KIR

CH2CNK–H2O

13.2

55.2

HP MS

1988MEO

(1) 14.3 (2) 15.2

59.8 63.6

(1) HP MS (2) HP MS

(1) 1971PAY/YAM (2) 1980LEE/KEE

ONK(H2O)x–H2O xZ0 1

(NO2)K(H2O)x–H2O xZ0

(continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1224

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.3 (continued) BDEs in Negative Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

1

2

3 N

(NO3)K(H2O)x–H2O xZ0

1

2

N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(3) (4) (1) (2) (4) (1) (2) (4) (2) (5)

14.5 15.5G1.5 12.9 13.6 13.0G1.5 10.4 11.7 11.5G1.5 11.6 w10.5

60.7 64.9G6.3 54.0 56.9 54.4G6.3 43.5 49.0 48.1G6.3 48.5 w44

(3) HP MS (4) ES MS

(3) 1985SIE (4) 1995BLAKLA

(5) Extrapolate

(5) This volume

(1) (2) (3) (4) (5) (3) (4) (5) (2) (4) (5) (6)

12.4 14.6 14.8 14.1 10.6 14.3 12.2 11.5 13.8 10.9 12.0 w10.5

51.9 61.1 61.9 59.0 44.4 59.8 51.0 48.2 57.7 45.6 50.2 w44

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

(6) Extrapolate

(6) This volume

HP MS HP MS MS ES MS Photodet.

1971PAY/YAM 1980LEE/KEE 1984ARN/QIU 1995BLA/KLA 2002WAN/YAN

(NO3)K(HNO3)–H2O

12.9

54.0

MS

1982ARN/VIG

c-C4H4NK(H2O)x–H2O xZ0 1

15.7 12.1

65.7 50.6

HP MS

1988MEO

C6H5NOK 2 –H2O C6H5NOK 2 –2H2O

13.5G0.1 12.4G0.1

56.5G0.4 51.9G0.4

HP MS

1985SIE

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

AcAlaNK(H2O)x–H2O xZ0 1 AcZCH3CO AlaZNHCH(CH3)CO

1225

15.2 13.0

63.6 54.4

HP MS

1988MEO(c)

ImNK(H2O)x–H2O xZ0 15.2 1 11.8 2 12.9 ImNZimidazolyl, N2C3H3

63.6 49.4 54.0

HP MS

1988MEO(c)

(CH3COOK AcAlaNH) –H2O AcZCH3CO AlaZNHCH(CH3)CO

13.2

55.2

HP MS

1988MEO(c)

ONK–H2S

5.6

23.3

PES

2002HEN/CLE

CNK–H2S

(1) 19.8 (2) 18.9

82.8 79.1

(1) ICR (2) HP MS

(1) 1987LAR/MCM(b) (2) 1988MEO(d)

ONK–H2S

5.6

23.4

PES

2002HEN/CLE

NOK 2 –CH3

12.9G4.6

54.0G19.3

Derived

1978COM/REI(b)

NOK 2 –H2O2 NOK 3 –H2O2

20.2 19.2

84.4 80.2

FA

1984BOH/FAH

(NO2)K(HNO2)x–HNO2 xZ0 1

32.5 21.3

136.0 89.1

HP MS

1980LEE/KEE

(NO3)K(HNO3)x–HNO3 xZ0 1

(1) O23 (1) 18.3

O96 76.6

(1) FA

(1) 1977DAV/FEH (continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1226

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.3 (continued) BDEs in Negative Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

2

3 4 5 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (2) (3) (4) (1) (2) (3) (2) (2) (2) (5)

16.0 17.7 20.0 16.1 13.9 16.0 9.3 7.4 4.6 w9.3

kJ/mol

Methods (reference in parentheses)

References

66.9 74.1 83.7 67.4 58.2 66.9 38.9 31.0 19.2 w39

(2) HP MS (3) HP MS (4) MS

(2) 1980WLO/LUC (3) 1980LEE/KEE (4) 1984ARN/QIU

(5) Extrapolate

(5) This volume

ONK–NH3

10.4

43.4

PES

2002HEN/CLE

NHK 2 (NH3)x–NH3 xZ0 1

12.5 10.6

52.2 44.4

PES

1995SNO/COE

CNK–PF3 –AsF3

15.3 24.9

64.0 104.2

ICR

1988LAR/SZU

CNK–OCF2 –OSF2

23.5 15.8

98.3 66.1

ICR

1988LAR/SZU

NOK 3 –ClONO2

14.6 w 26

61 w 109

Fast flow tube

1997WIN/MER

CNK–CF3H –CHCl2F –CHCl3 –CH2Cl2

17.0 17.8 18.2 16.3

71.1 74.5 76.1 68.2

ICR

1987LAR/MCM(b)

CH2CNK–CH3CN c-C4H8NK–CH3CN

12.8 15.8

53.6 66.1

HP MS

1988MEO

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1227

CNK–OPF3 –SF4 –SiF4

23.5 25.8 27.2

98.3 107.9 113.8

ICR

1988LAR/SZU

(C6H5NO2)K–B, BZSiF4 (p-F-C6H4NO2)K–B (p-Cl-C6H4NO2)K–B (p-CH3-C6H4NO2)K–B (p-NO2-C6H4NO2)K–B

35G2 33G2 32G2 35G3 21G1

146G8.4 138G8.4 134G8.4 146G12.6 88G4.2

HP MS

2001WIL/KNI

CNK–CH3OH

(1) 16.5 (2) 15.7G0.8

69.0 65.7G3.3

(1) ICR (2) Derived

(1) 1987LAR/MCM(b) (2) 1988LAR/SZU

NOK 2 –CH3OH

17.4G0.2

72.8G0.8

HP MS

1985SIE

c-C4H4NK–CH3OH

18.6

77.8

HP MS

1988MEO

C6H5NOK 2 –CH3OH

15.1G0.2

63.2G0.8

HP MS

1985SIE

Y-C6H4NOK 2 –CH3OH YZ3-F 3-CF3 4-CN 4-OMe

15.8 14.6 13.9 13.7

66 61 58 57

HP MS

1987CHO/GRI

AcAlaNK–CH3OH

18

75.3

HP MS

1988MEO(c)

AcZCH3CO AlaZNHCH(CH3)CO ImNK–CH3OH

17.1

71.5

HP MS

1988MEO(c)

ImNZimidazolyl, N2C3H3 CNK–CH3CN (1) 16.4 (2) 15.7

68.6 65.7

(1) ICR (2) HP MS

(1) 1987LAR/MCM(b) (2) 1994HIR/YAM

CH2CNK–CH3CN

65.7

Review

1994HIR/YAM

15.7

(continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1228

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.3 (continued) BDEs in Negative Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

NOK 2 –CH3CN

13.4G0.2

56.1G0.8

HP MS

1985SIE

CH2CNK–CH3CN

15.7

65.7

HP MS

1994HIR/YAM

Y-C6H4NOK 2 –CH3CN YZ3-CF3 4-CN 4-OMe

13.3 13.9 13.8

56 58 58

HP MS

1987CHO/GRI

CNK–CF3CFO –CH3SiF3

24.6 22.6

102.9 94.6

ICR

1988LAR/SZU

(NO2)K(B)x–B, BZMeNO2 xZ0 (1) (2) 1 (2) 2 (2) 3 (2) N (3)

14.3G0.1 14.5G0.5 12.4G0.5 11.3G0.8 9.7G0.3 w8.6

59.8G0.4 60.7G2.1 51.9G2.1 47.3G3.3 40.6G1.2 w36

HP MS

(1) 1985SIE (2) 2003WIN

(3) Extrapolate

(3) This volume

CH2NOK 2 (B)x–B BZMeNO2 xZ0 1 2 3 N

(1) (1) (1) (1) (2)

15.9G0.5 13.3G0.7 12.6G0.5 11.4G0.2 w8.6

66.5G2.1 55.6G2.9 52.7G2.1 47.7G0.8 w36

(1) HP MS

(1) 2003WIN

(2) Extrapolate

(2) This volume

(1) (2) (1) (2) (2)

15.2G0.2 12.8G0.3 13.3G0.2 12.8G0.3 10.4G0.5

63.5G0.8 53.6G1.3 55.6G0.8 53.6G1.3 43.5G2.1

(1) PES (2) HP MS

(1) 1996COM/CAR (2) 2003WIN

MeNOK 2 (B)x–B, BZ MeNO2 xZ0 1 2

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

3 N

(2) 8.4G0.2 (3) w8.6

35.1G0.8 w36

MeNOK 4 (B)x–B, BZ MeNO2 xZ0 1 2 3 N

(1) (1) (1) (1) (2)

13.0G0.8 10.9G0.6 9.5G0.9 6 w8.6

54.4G3.3 45.6G2.5 39.7G3.8 25 w36

(NO2)K(B)x–B, BZEtNO2 xZ0 1 2 3 N

(1) (1) (1) (1) (2)

15.8G0.5 14.9G0.5 11.8G0.5 11.0G0.5 w10

66.1G2.1 62.3G2.1 49.4G2.1 46.0G2.1 w42

EtNOK 2 (B)x–B, BZEtNO2 xZ1 2 3 N

(1) (1) (1) (2)

14.6G0.2 13.6G0.3 11.9G0.5 w10

61.1G0.8 56.9G1.3 49.8G2.1 w42

EtNOK 4 (B)x–B, BZEtNO2 xZ0 1 2 3 N

(1) (1) (1) (1) (2)

14.3G0.8 12.7G0.8 11.3G0.9 10.5G0.9 w10

59.8G3.3 53.1G3.3 47.3G3.8 43.9G3.8 w42

C2H3NOK 2 (B)x–B BZEtNO2 xZ1 2

15.7G0.8 15.2G0.8

C2H4NOK 2 (B)x–B, BZEtNO2 xZ1 2

16.2G0.8 15.4G0.8

1229

(3) Extrapolate

(3) This volume

(1) HP MS

(1) 2003WIN

(2) Extrapolate

(2) This volume

(1) HP MS

(1) 2004WIN

(2) Extrapolate

(2) This volume

(1) HP MS

(1) 2004WIN

(2) Extrapolate

(2) This volume

(1) HP MS

(1) 2004WIN

(2) Extrapolate

(2) This volume

65.7G3.3 63.6G3.3

HP MS

2004WIN

67.8G3.3 64.4G3.3

HP MS

2004WIN (continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1230

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.3 (continued) BDEs in Negative Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) (NO2)K(B)x–B, BZ EtONO2 xZ0 1 2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

20.9G1.0 8.5G0.5 7.3G0.7

kJ/mol

Methods (reference in parentheses)

References

87.4G4.2 35.6G2.1 30.5G2.9

HP MS

1983WLO/LUC(b)

(NO2)K(SO2)–C2H5ONO2 7.4

31

HP MS

1983WLO/LUC

(NO3)K(B)x–B BZEtONO2 xZ0 1

17.2 7.2

72 30.1

HP MS

1983WLO/LUC(b)

CNK–C2H5OH –CH2FCH2OH –CH2ClCH2OH –CF3CH2OH

17.4 20.4 21.1 24.6

72.8 85.4 88.3 102.9

ICR

1987LAR/MCM(b)

CNK–CF3OCHF2 –CH3C(O)CH3

18.7 14.7

78.2 61.5

ICR

1987LAR/MCM(b)

NOK 2 –B BZCH3C(O)CH3 C6H5NOK 2 –B

15.9G0.1

66.5G0.4

HP MS

1985SIE

14.2G0.2

59.4G0.8

(HCONCH3)K–B BZHCONHCH3 (pyrroleH)K–B

28G2

117G8.4

HP MS

1988MEO(c)

26G2

109G8.4

CNK–CF3C(O)CF3 –CHF2C(O)CHF2 –CF3C(O)CHF2

20.4 22.0 25.8

85.4 92 108

ICR

1987LAR/MCM(b)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1231

c-C4H8NK(B)x–B BZ(CH3)2CO xZ0 1

13.1 10.7

54.8 44.8

HP MS

1988MEO

CNK–CF3CF2CFO

27.6

116

ICR

1988LAR/SZU

NOK 2 –B, BZCH3SOCH3 C6H5NOK 2 –B

19.2 16.8G0.1

80.3 70.3G0.4

HP MS

1985SIE

Y-C6H4NOK 2 –CH3SOCH3 YZ3-CF3 4-CN 4-OMe

14.6 16.0 16.3

61 67 68

HP MS

1987CHO/GRI

c-C4H8NK(B)x–B BZc-C4H8NH xZ0 1

26.9 17.1

113 71.5

HP MS

1988MEO

CNK–CF3CH2OH –i-CH3CH2OH

24.0G0.8 16.7G0.8

100.4G3.3 69.9G3.3

Derived

1988LAR/SZU

CNK–CHF2CH2F –NCC(O)C2H5 –i-C3H7OH –(CH2F)2CHOH –t-C4H9OH

18.4 17.4 18.1 23.5 18.1

77.0 72.8 75.7 98.3 75.7

ICR

1987LAR/MCM(b)

ONK–HOC2H4OH

27.0

112.9

PES

2002HEN/CLE

(HCONCH3)K–B BZCH3CONHCH3 (pyrroleH)K–B

27 27

113 113

HP MS

1988MEO(c) (continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1232

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.3 (continued) BDEs in Negative Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(CH3COO)K(B)x–B BZCH3CONHCH3 xZ0 1

25.4 17.6

106 73.6

HP MS

1988MEO(c)

CNK–(CF3)2(CH3)COH

25.7

108

ICR

1987LAR/MCM(b)

NOK 2 –Me3C(O)H C6H5NOK 2 –Me3C(O)H

19.6G0.2 16.4G0.2

82.0G0.8 68.6G0.8

HP MS

1985SIE

CNK–pyrrole

(1) 19.5 (2) 23.4

81.6 97.9

(1) ICR (2) HP MS

(1) 1988LAR/MCM (2) 1998MEO(d)

NOK 3 –Fe(NO3)3

w66

w276

ESI

2003LI/BYE

CNK–(CH3O)3B CNK–(C2H5)3B

19.6 O33

82 O138

ICR

1988LAR/SZU

3-NO2C6H4NOK 2 –SF6 4-NO2C6H4NOK 2 –SF6

!8.4 !8.5

!35.1 !35.6

IMKB

1986CHO/KEB

118 96.7

HP MS

1988MEO(c)

126 113.8G5.8

(1) HP MS (2) IR radiation

(1) 1988MEO(c) (2) 1998JOC/WIL

28.3 AcAlaNK–AcAlaNH ImNK–AcAlaNH 23.1 ImNZimidazolyl, N2C3H3 AcZCH3CO AlaZNHCH(CH3)CO

(CH3COO)K(L)x–L LZAcAlaNH xZ0

(1) 30.2 (2) 27.2G1.4

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1233

1 AcZCH3CO AlaZNHCH(CH3)CO

(2) 21.2

88.7

(CH3COO)K(H2O)– AcAlaNH

27.6

116

HP MS

1988MEO(c)

(CN)K–CH3C(O)-AlaOCH3 AlaZNHCH(CH3)CO

26.4

111

HP MS

1988MEO(c)

ImNK–ImNH 26.4 (CH3COO)K–ImNH 27.7 ImNZimidazolyl, N2C3H3

111 116

HP MS

1988MEO(c)

AcAlaNK–pyrrole AcZCH3CO AlaZNHCH(CH3)CO

24.0

100

HP MS

1988MEO(c)

9.5 17.5

39.6 73.3

PES

2002LEB/SCH

14.5 23.8

60.8 99.5

PES

2002BAR/SCH

14.2 15.0 20.0 18.8 21.2

59.4 62.8 83.7 78.7 88.7

HP MS

1986GRI/CHO

(NO)K(C6H6)x–C6H6 xZ0 1

(NO)K(C10H10)x–C10H10 xZ0 1 C10H10Znaphthalene NO2−

YZH p-F m-CN p-CN m-NO2

Y

(continued)

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

1234

Comprehensive Handbook of Chemical Bond Energies

Table 25.1.3 (continued) BDEs in Negative Nitrogen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

m-CH3O 3-CN, 5-NO2

20.5 23.5

85.8 98.3

NOK–pyridine –pyrimidine

13.6 16.6

56.9 69.5

PES

2002BAR/SCH

(Py)K(Py)x–Py PyZpyridine xZ3 4 5 6

3.7 3.5 3.7 1.6

15.4 14.5 15.4 6.8

PES

1999HAN/SON

(CO2)(Py)K(Py)x–Py PyZpyridine xZ0 1 2 3 4

6.7 5.5 5.5 4.2 3.7

28.0 23.1 23.1 17.5 15.4

PES

2000HAN/CHU

31.1G3.2 33.4G4.4 34.4G4.2 34.8G4.6 40.6G1.8 30.7G3.0

130G13.5 140G18.4 144G17.4 146G19.3 170G7.7 128G12.5

IR radiation

1999STR/SCH

dAMPK–dAMP dCMPK–dCMP dTMPK–dTMP dGMPK–dGMP dGMPK–dCMP dAMPK–dTMP dAMPZadenosine dCMPZcytosine dTMPZthymine dGMPZguanosine

7366—CHAPTER 25—6/2/2007—10:16—CRCPAG—15381—XML MODEL B – pp. 1163–1241

BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1235

25.2 Phosphorus clusters/complexes 25.2.1 Phosphorus-cation clusters/complexes Table 25.2.1 BDEs in Phosphorus-Cation Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

PC–P

(1) 116 (2) 115G12

485 481G50

(1) Derived (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

PC–N

(1) 116 (2) 115.4G5

486 483G21

(1) Derived (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

(1) 70.5G5 (2) 77.5G0.4 (3) 78.8G0.5

295G21 324.3G1.7 329.6G2.1

(1) Derived (2) Review (3) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1993BAL/CHU (3) 1996NIST

(2) 82.2G2 (2) 81.5G2

343.9G8.4 341.0G8.4

PC–F

(1) 155G25 (2) 117.2G2.0

649G105 490.6G8.4

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

PC–Cl

69

289

Derived

1974GUR/KAR

PC–O

(1) 189.1G2.0

791.3G8.4

(1) 1996NIST

(2) 191

800

(1) Derived from IP in ref. (2) Derived

(1) 150G50 (2) 145G6

628G209 606G34

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

PC(H)x–H xZ0

1 2

PC–S

(2) 2003DEA/LI

(continued)

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Table 25.2.1 (continued) BDEs in Phosphorus-Cation Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

PC–C

122G10

512G42

Derived

1974GUR/KAR

H4PC–H2O

13

54.4

ICR

1986KEE/CAS

(H4P)C(PH3)x–PH3 xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

48.1 38.5 30.5 27.2 23 w15

(1) MS

(1) 1974LON/FRA

(2) Extrapolate

(2) This volume

P2HC 5 –PH3 P3HC 6 –PH3

9 10.8

38 45

MS

1974LON/FRA

11.5 9.2 7.3 6.5 5.5 w3.5

25.2.2 Phosphorus-anion clusters/complexes Table 25.2.2 BDEs in Phosphorus-Anion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

PK–H

77.5G0.7

324.2G3.0

–In

75.1G2.5

314G10.5

113.3G1.2

(1) 12.9G0.3 (2) 12.6

PK–P

(PO3)K(H2O)x–H2O xZ0

Methods (reference in parentheses)

References

Derived from EA in ref.

1996NIST

474.1G5.0

Derived from EA in ref.

1996NIST

53.9G1.4 52.7

(1) HP MS (2) ES MS

(1) 1989KEE/CAS (2) 1996BLA/HO

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BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1 2 3 N

(1) (2) (1) (1) (3)

11.4 11.4 16.3 11.0 w10.5

47.7 47.7 68.2 46.0 w44

1237

(3) Extrapolate

(3) This volume

(H2PO2)K(H2O)x–H2O xZ1 2

13.4 11.7

56.1 49.0

ES MS

1996BLA/HO

(OH)(PO2)K(H2O)x–H2O xZ1 2

13.6 12.2

56.9 51.0

ES MS

1996BLA/HO

(1) (1) (2) (2)

58.6 51.5 54.8 49.4

ES MS

1996BLA/HO

(OH)2(PO2)K(H2O)x–H2O xZ0 1 2

14.0 12.3 13.1 11.8

(OH)3POK–H2O (OH)4PK–H2O H6O4PK–H2O H6O5PK–H2O

13.4G1.5 13.6G1.5 11.7G1.5 12.2G1.5

56.1G6.3 56.9G6.3 49.0G6.3 51.0G6.3

ES MS

1995BLA/KLA

(PO3)K(D2O)x–D2O xZ0 1 2 3 N

(1) (1) (1) (1) (2)

52.6G0.9 47.8G1.0 68.2G1.2 46.1G1.8 w44

(1) HP MS

(1) 1989KEE/CAS

(2) Extrapolate

(2) This volume

H2POK 4 –H3PO4

28.8G0.9

120.6G3.9

IR radiation

1999STR/SCH

F2O2PK–AlF4Na –F2NaO2P –AlF4K

45.2G5 58G20 42.3G5

189G21 243G84 177G21

MS

1989MAV/MIL

12.6G0.2 11.4G0.2 16.3G0.3 11.0G0.4 w10.5

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25.3 Arsenic clusters/complexes Table 25.3 BDEs in Arsenic Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

GaAs(surf.)–As

60

251

Absorption

1968ART

GaAs(100, surf.)–Sb

10.4 (phys)

43.4

PED

1997ASC/AVI

GaAs(100, surf.)–Sb

57.7

241

AES

1980NAG/MIY

GaAs(100, surf.)–In

53.5G1.2

223.8G4.8

XPS

1989MCC/DON

GaAs(110, surf)–He

0.10, at 0 K

0.41

Scattering

1987DOA/NGU

GaAs(110, surf.)–H2

13.8

57.7

TPD

1984MOK/KOH

GaAs(110, surf.)–NO2

6G2

25G8

Mol. Beam

1993FEL/BAH

GaAs(110, surf.)–NO2

9G2

38G8

Mol. Beam

1995BAH/FEL

AsC–As

(1) 63G10 (2) 95.7 (3) 87G5.3

264G42 400.3 364G22

(1) Derived (2) Derived (3) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996SMI/YAT (3) 1996NIST

AsC–P

87.8G14.2

367G59

Derived from IP in ref.

1996NIST

AsC–H

69.5G2.4

290.8G3.0

Derived from IP in ref.

1996NIST

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BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

1239

AsHC 2 –H

61.3

257

UV PI

1998RAN/SHU

AsC–O

118.3

495

Spectroscopy

2000NAG/RAJ

AsC–S

103.5G3.0

433G12.5

Spectroscopy

2000RAJ/NAG

I2AsC–acetone –benzene

25.4G4.6 18.4G4.6

106G17 77G17

FT-ICR

1995SIE/GRI

AsK–As

(1) 63.2 (2) 89.6G2.5

264.2 374.8G10.5

(1) Derived (2) Derived from IP in ref.

(1) 1996SMI/YAT (2) 1996NIST

(2) 69.8G2.4

292G10

–H

25.4 Antimony clusters/complexes Table 25.4 BDEs in Antimony Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Sb(surf.)–Sb

33.9

141.8

Mol. beam

1994YAN/YAM

Sb(H, surf.)–Sb

31.1

130.3

TPD

1996NAK/KIM

GaAs(100, surf.)–GaSb

19.6 (phys)

82.0

MBE

1999WAN/FOR

GaAs(100, surf.)–GaSb

49.6

207.4

MBE

1999WAN/FOR

Cl5Sb–CH3CHCHCHO –CH3CHCHC(O)OCH3 –CH3C(CH3)CHCHO –CH3CHCHCN

21.2G0.4 18.0G0.4 24.3G0.5 15.3G0.3

88.7G1.7 75.3G1.7 101.7G2.1 64.0G1.3

Calorimetry

1982CHI/MUL

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 25.4 (continued) BDEs in Antimony Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) SbC–Sb

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 74.7 (2) 76.9G1.5

312.5 322G6.3

(1) Derived (2) Derived from IP in ref.

(1) 1996SMI/YAT (2) 1996NIST

SbC(Sb)x–Sb xZ1 2 3

O66 O66 O66

O276 O276 O276

Evaporation

1995BRE/CHA(b)

SbC–H

54.7G1.0

228.8G4.2

Derived from IP in ref.

1996NIST

–S –P

96.0G6.9 56.2G6.9

402G29 235G29

SbK–Sb

77.5G2.0

324.3G8.4

1996NIST

SbK 2 –Sb2

27.6G3

115.5G12.6

Derived from DfH0 in ref.

25.5 Bismuth-ion clusters/complexes Table 25.5 BDEs in Bismuth Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Bi(polycs. surf.)–H

36

151

Electrochemical

1970KRI

BiC–Bi

(1) 44.5 (2) 47.6G2.4

186 199G10

(1) Derived (2) Derived from IP in ref.

(1) 1996SMI/YAT (2) 1996NIST

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BDEs in the N-, P-, As-, Sb-, Bi-Clusters and Complexes

BiC–O

(1) 41.0G12

172G50

(2) 41.6

174

BiC–S

42.8G12

179G50

–Te

29.8G12

125G50

BiC–Sb

43.9G7.0

BiC–Tl

1241

(1) Derived from IP in ref. (2) Derived

(1) 1996NIST

Derived from IP in ref.

1996NIST

184G29

Derived from IP in ref.

1996NIST

24.0G10

100G42

Derived from IP in ref.

1996NIST

BiC(H2O)x–H2O xZ0 1 2 3 4 5 N

(1) (1) (1) (1) (1) (1) (2)

95.4 74.1 58.6 50.2 43.9 40.6 w44

(1) HP MS

(1) 1974TAN/CAS

(2) Extrapolate

(2) This volume

BiC(NH3)x–NH3 xZ0 1 2

35.5 23.2 13.4

149 97.1 56.1

HP MS

1978CAS

BiC–C6H6

%35.5

%149

PD

1992WIL/YEH

BiK–Bi

(1) 56.1G0.3 (2) 65.5 (3) 55.5G2.4

234.7G1.2 274 232G10

(1) PES (2) Derived (3) Derived from IP in ref.

(1) 1991POL/HO (2) 1996SMI/YAT (3) 1996NIST

22.8 17.7 14.0 12.0 10.5 9.7 w10.5

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(2) 2004LAV/BLA

chapter twenty-six

BDEs in the O-, S-, Se-, Te-clusters and complexes 26.1 Oxygen and the ion clusters/complexes 26.1.1

Oxygen clusters/complexes

Table 26.1.1 BDEs in Oxygen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

O2–He

0.06, at 0 K

0.26

Scattering

1987BEN/CAS

NO–He

0.06, at 0 K

0.26

Scattering

1987BEN/CAS

SO–He

w0.1, at 0 K

w0.3

Mol. beam

1997AQU/ASC

H2O–He

0.06, at 0 K

0.27

Scattering

2005AQU/COR

O2–Ne

0.13, at 0 K

0.58

Scattering

PIR/PIR

HO–Ne

0.15, at 0 K

0.61

Spectroscopy

1993HEA

SO–Ne

w0.1, at 0 K

w0.5

Mol. beam

1997AQU/ASC (continued)

1243

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Table 26.1.1 (continued) BDEs in Oxygen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

H2O–Ne

0.13, at 0 K

0.55

Scattering

2005AQU/COR

Dimethylether–Ne

0.2, at 0 K

1.0

Spectroscopy

2003MAR/CAM

Propylene oxide–Ne

0.3, at 0 K

1.2

Spectroscopy

2002BLA/MAR(b)

2,5-dihydrofuran–Ne

0.3, at 0 K

1.2

Spectroscopy

1999MAR/FAV

O2–Ar

(1) w0.29, at 0 K w1.2 (2) 0.27 1.11

(1) Review (2) Scattering

(1) 1976BLA/EWI (2) 1981PIR/VEC

HO–Ar

(1) 2.1, at 0 K (2) 2.14

8.6 8.96

Spectroscopy

(1) 1993HEA (2) 1999CAR/MIL

SO–Ar

w0.4, at 0 K

w1.6

Mol. beam

1997AQU/ASC

CO–Ar

0.3, at 0 K

1.3

Spectroscopy

1995KRA/CRE

CO2–Ar

0.48, at 0 K

1.98

Photofrag.

2000OUD/MIL(b)

H2O–Ar

(1) 0.4, at 0 K (2) 0.3

1.7 1.4

(1) IR (2) Scattering

(1) 1993COH/SAY (2) 2005AQU/COR

H2O(ice, surf.)–Ar

2.8

11.7

Review

1991ELL/TUR

CH3OH–Ar

0.43, at 0 K

1.8

Spectroscopy

2004MAR/CAM

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BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1245

C2H5OH–Ar sec-C4H9OH–Ar

0.50 0.55

2.1 2.3

Phenol–Ar

1.04G0.04, 0 K

4.35G1.67 MATI

Furan–Ar

(1) w0.67, at 0 K w2.82 (2) 0.74 3.01

Dibenzofuran–Ar Dibenzo-p-dioxin–Ar

%1.49G03, at 0 K 1.51G0.05

O–Kr

!2

!8

Review

1974GUR/KAR

O2–Kr

(1) w0.33 (2) 0.31

w1.38 1.29

Scattering

(1) 1972TUL/LEE (2) 1998AQU/ASC

HO–Kr

(1) 4.91, at 0 K (2) 5.07

20.5 21.2

Spectroscopy

(1) 1993HEA (2) 1999CAR/MIL

SO–Kr

w0.5, at 0 K

w2

Mol. beam

1997AQU/ASC

H2O–Kr

0.39, at 0 K

1.65

Scattering

2005AQU/COR

Propylene oxide–Kr

0.7, at 0 K

3

Spectroscopy

2002BLA/MAR

Oxirane–Kr

0.7, at 0 K

3.1

Spectroscopy

2002VEL/MIL

Propylene oxide–Kr

0.8, at 0 K

3.6

Spectroscopy

2003BLA/MEL

Dibenzo-p-dioxin–Kr

1.8, at 0 K

7.6

Spectroscopy

1995GRE/NEU

Spectroscopy

%6.23G0.14 MATI

1999HAI/DES

(1) 1983KUK (2) 1995BET/BET

1997GRE/STU

6.30G0.22

(continued)

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

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Comprehensive Handbook of Chemical Bond Energies

Table 26.1.1 (continued) BDEs in Oxygen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

2,5-dihydrofuran–Kr

0.8, at 0 K

3.5

Spectroscopy

2000VEL/MEL

O–Xe

8.7

36.4

Review

1974GUR/KAR

O2–Xe

0.35, at 0 K

1.47

Scattering

1998AQU/ASC

SO–Xe

w0.5, at 0 K

w2.2

Mol. beam

1997AQU/ASC

H2O–Xe

0.46, at 0 K

1.92

Scattering

2005AQU/COR

Oxirane–Xe

w0.9, at 0 K

w3.9

Spectroscopy

2002VEL/FAV

H2O(ice, surf.)–220Rn

4.6G0.4

19.2G1.6

GC

2000EIC/ZIM

Poly(methylmethacrylate)–Pb

3.0G0.2

12.7G0.7

Calorimetry

2005DIA/ZHU

ClO3–F

57

238

EI

1957DIB/REE

H2O(ice, surf.)–O

8.4–9.6

35–40

Kinetics

2003MUR/PLA

CO–para-H2 –ortho-D2

(1) w0.06, at 0 K w0.26 (2) w0.09 w0.36

IR

(1) 1998MCK (2) 2000MCK

H2O(ice, surf.)–D2

1.8

TPD

2006AMI/FIL

7.6

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BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1247

O2–O2

(1) w0.24, at 0 K w1.0 (2) 0.23 0.96

(1) Review (2) Spectroscopy

CO–CO

1.70G0.05

Phenol–CO

1.88G0.06, at 0 K 7.87G0.25 MATI

1999HAI/DES

H2O(ice, surf.)–CO

(1) 3.5 (2) w2.4 (3) 2.5G0.05

14.6 w10 10.4G0.2

(1) Review (2) FT-IR (3) IR

(1) 1991ELL/TUR (2) 1998ALL/VER (3) 2000MAN/ROU

Ti2O(110, surf.)CO–CO

9.9

41.4

TPD

1995LIN/LU

Ni(110, surf.)CO–CO

1.8 (phys.)

7.4

Diffraction

1993XIA/XIE

CO–N2

1.7

7.1

TPD

2005OBE/BRO

H2O–N2

0.8G0.4

3.2G1.7

CRDS

2005COR/HOD

Phenol–N2

(1) 1.27, at 0 K (2) 1.24G0.06

5.32 MATI 5.19G0.25

(1) 1998HAI/GEP (2) 1999HAI/DES

H2O(ice, surf.)–N2

2.8

11.7

Review

1991ELL/TUR

H2O(ice, surf.)–NO

4.8G0.5

20G2.3

CL

2002RAU/EIC

CO–HF

2.09G0.0.25, 0 K 8.76G.1.04 Photofrag.

2000OUD/MIL

H2O–HF

6.2, at 0 K

1975THO

7.11G0.21 TPD

25.9

IR

(1) 1976BLA/EWI (2) 1998CAM/BIE

2005OBE/BRO

(continued)

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

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Comprehensive Handbook of Chemical Bond Energies

Table 26.1.1 (continued) BDEs in Oxygen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

OCO–HF

1.93G0.01, 0 K

8.06G0.05 Photofrag.

1998OUD/MIL

(CH2)2O–HF

5.48, at 0 K

22.9

FT-IR

2005ASS/GOU

CH3OCH3–HF CH3OC2H5–HF C2H5OC2H5–HF

10.3, at 0 K 8.84 7.17

43.1 37.0 30.0

IR

1971THO

OCO–HCl

w1.23, at 0 K

w5.14

IR

1996OUD/OLS

(1) Raman (2) NMR

(1) 1968GOV/CLA (2) 1974GIL/BER

1960INS/DIC

CH3OCH3–HCl

(1) 7.1G0.8, at 0 K 29.7G3.3 (2) 6.7G0.4 28.0G1.7

C2H5OC2H5–HCl

4.7G0.7, at 0 K

19.7G2.9

IR

H2O(ice, surf.)–HCl

(1) (2) (3) (4) (5)

46.0 33G5 28G2 R34.7 24G2

(1) (2) (3) (4) (5)

H2O–HOO

9.4

39.3

Est. by exp.

2000ALO/FRA

H2O(ice, surf.)–O3

4.8

20

FT-IR

2001BOR/CHI

H2O(ice, surf.)–CO2

(1) 6.2 (2) 5.1G0.5

25.9 21.2G1.9

(1) Review (2) TR mol. beam

(1) 1991ELL/TUR (2) 2004AND/NAG

11.0 7.9G1.2 6.7G0.5 R8.3 5.7G0.5

Review Adsorption Desorption Mol. beam Mol. beam

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

(1) (2) (3) (4) (5)

1991ELL/TUR 1994GRA/ROB 1999ISA/SIT 2000AND/NAG 2005LOH/DAY

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1249

H2O(ice, surf.)–NO2

5.3G0.2

22G1.0

CL

2002RAU/EIC

H2O–H2O

(1) 5.35 (2) 3.59G0.5, 373 K (3) 3.66, 0 K (4) 4.3G1.4 (5) 3.8G0.1, 270–315 K (3) 3.66G0.5 (6) 2.50G0.3 (7) 5.1G0.5 (8) 3.4G0.13, at 289–370 K

22.4 15.0G2.1

(1) Re-analysis (2) TC

(1) 1974GUR/KAR (2) 1979CUR/FRU

15.3 18G6 15.9G0.3

(3) Spectroscopy (4) PA-kinetics (5) CRDS

(3) 1999FEL/LEF (4) 2004GOE/WEN (5) 2005COR/HOD

15.3G2.1 10.5G1.3 21.3G2.1 14.2G5.4

(6) Raman (7) Raman (8) Raman

(6) 2005SUN/ZHE (7) 2004WAL (8) 2005BET/SOR

H2O(ice, surf.)–H2O(ice) 5.6 (diffusion)

23.4

NMR

1987MIZ/HAN

H2O(ice, surf.)–H2O

46.9 58.2G0.8 50.2G5.9 57.7G0.8 61.9G1.7

(1) NMR (2) TPD (3) Kinetics

(1) 1987MIZ/HAN (2) 2003SMI/LIV (3) 2006PRA/BER

44.3

Est. by exp.

2000NOP

D2O–D2O HDO–HDO HDO–H2O

–H18 2 O –D2O

H2SO4–H2O

C6H5OH–H2O

(1) (2) (3) (2) (2)

11.2 13.9G0.2 12.0G1.4 13.8G0.2 14.8G0.4

10.6

(1) 5.60G0.11, 0 K 23.43G0.46 (1) PES (2) 5.48 22.91 (2) MATI

1-Naphthol–H2O

5.82, at 0 K

Neutral red–H2O

2.40G0.01

H2O–SO3

13

24.34

10.05G0.06

54.4

(1) 1998COU/MON (2) 2000BRA/MEH

MATI

2000BRA/MEH

Fluorescence

2005SIN/WAL

Flow reactor

1996LOV/HAN (continued)

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

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Comprehensive Handbook of Chemical Bond Energies

Table 26.1.1 (continued) BDEs in Oxygen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

HOH–NH3

2.92

12.21

Review

1995HIL/FRA

Phenol–NH3

O6.1

O25.5

Review

2002MON/DIM(b)

1-Naphthol–NH3 –ND3

7.66G0.01 8.01G0.04

32.05G0.04 33.51G0.17

SEP-R2PI

1995BUR/DRO

H2O(ice, surf.)–HONO –HNO3

7.6G0.4 10.5G0.5

32G1.7 44G2.3

CL

2002RAU/EIC

H2O(ice, 1000, surf.)– CHF3

w5.5

w23

HAS

1999GRA/MEN(b)

Oxirane–CHF3

(1) 1.6 (2) 2.8

6.7 11.6

(1) FT-MW (2) IR

(1) 2004ALO/ANT (2) 2005DEL/HER

Oxirane–CHClF2 –CHCl2F –CHCl3

2.9 2.8 2.6

12.0 11.8 10.8

IR

2005DEL/HER

CH3OCH3–CHF3 –CHClF2 –CHCl2F –CHCl3

3.0 3.0 2.9 2.7

12.5 12.5 12.2 11.3

IR

2005DEL/HER

CH3COCH3–CHF3 –CHClF2 –CHCl2F –CHCl3

2.6 3.0 3.1 3.3

10.9 12.5 12.9 13.7

IR

2005DEL/HER

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1251

Dioxane–CHF3

w1.6

w6.8

FT-MW

2005FAV/GIU

Cyclobutanone–CHF3

1.8

7.5

Spectroscopy

2006OTT/CAM

H2O–CF2H2

1.8

7.5

MW spectra

1999CAM/MAL(b)

Oxirane–CF2H2

2.3

9.6

Spectroscopy

2006BLA/LOP

H2O(ice, surf.)–CH4

0.50G0.05 (phys.)

2.1G0.2

IR

2000MAN/ROU

H2O(ice)–CH4

4.8G0.1, 220 K

20.0G0.6

ESR

2005TAK/NAN

H2O–CH4

13.1G1.4, 250 K 54.8G5.7

ESR

2005TAK/NAN

HOO–CH3OH

9.1G0.5, at 0 K

38.1G2.1

UV-Visible spectr

2004CHR/OKU

CH3OH–CH3OH

(1) (2) (3) (4)

17.2G2.1 18.0 14.7G3.8 13.4G0.4

(1) NMR (2) Virial coeffic. (3) TC (4) IR

(1) (2) (3) (4)

CF3CH2OH–CH3OH C3F6HOH–CH3OH

7.3G0.2 10.4G0.3

30.5G0.8 43.5G1.3

PVT

1988CUR/BLA

Phenol–CH3OH

6.11G0.18, at 0 K

25.56G 0.75

PES

1998COU/MON

1-Naphthol–CH3OH

7.56G0.39

SEP-R2PI

1995BUR/DRO

4.1G0.5 4.3 3.5G0.9 3.2G0.1

31.63G1.63

1969CLA/GOV 1970KUD/EUB 1981FRU/CUR 1990BIZ/STO

(continued)

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

1252

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.1 (continued) BDEs in Oxygen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

ROH–HOR; RZMe, Et, 1-Oc, 2-Oc, t-Bu

%6

%25

Raman

2006PAO/SAS

HCOOH–HCOOH

15.15

63.4

Review

1978CHA/WZO

O2–C2F4

3.14G0.29

PI

1997CHE/PRE

13.14G1.21

H2O(ice, surf.)–C2H5OH (1) 14.8G0.4 (2) 13.6G2

61.9G1.7 57G8

(1) EI MS (2) Combined

(1) 2002SOK/ABB (2) 2004PEY/CAL

(CH3)2O–CF2CH2 (CH3)2O–CF2CFH

1.13 1.43

4.76 5.98

FT-MW

2003TAT/OGA

Phenol–C2H4

3.1, at 0 K

13.2

TR-IR-UV

2004KAY/EBA

C2H5OH–C2H5OH

(1) 5.0G1.2 (2) 3.7G0.9

20.9G5.0 15.5G3.8

(1) IR (2) TC

(1) 1973BAR/HAL (2) 1981FRU/CUR

CF3CH2OH–CF3CH2OH (1) 5.7G1.2 (2) 4.75

23.8G5.0 19.9

(1) IR (2) TC

(1) 1973BAR/HAL (2) 1978CUR/FRU

CH3C(O)H–CH3C(O)H

(1) 4.0 (2) 4.5

16.7 18.8

(1) PVT (2) Review

(1) 1960PRA/CAR (2) 1988CUR/BLA

CH3OCH3–CH3OCH3

1.3

5.4

MW spectra

2002TAT/LIU

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

O25.5 25.1

1253

Phenol–CH3OCH3

(1) O6.1, at 0 K (2) 6.0

CH3C(O)CH3– CH3C(O)CH3

(1) 3.9 (2) 3.22G0.35

CF3COOH– CH3C(O)CH3

(1) 14.4G1

60.2G4

(2) 7G1

29.3G4

H2O(ice, surf.)– CH3COOH

(1) 17.5G2.8 (2) 8.0G1.0

73.2G11.7 (1) EI MS 33.5G4.2 (2) Combined

(1) 2002SOK/ABB (2) 2005PIC/HOA

CH3COOH–CH3COOH

(1) 14.9 (2) 14.6

62.4 61.3

(1) Review (2) TC

(1) 1978CHA/WZO (2) 1980FRU/CUR

CF3COOH–CH3COOH

17

71.1

Vapor density

1966LIN/CHR(b)

CF3COOH–CF3COOH

(1) 14.5G0.6 (2) 12.0G1.0 (3) 13.7G2.0

60.7G2.5 50.2G4.2 57.2G8.4

(1) NMR (2) IR (3) TC

(1) 1975BAD/COU (2) 1977GER/TOK (3) 1980FRU/CUR

7.9G0.2 CH3OCH3–CF3COOH C2H5OC2H5–CF3COOH 8.4G0.2

33.1G0.8 35.1G0.8

IR

1977GER/TOK

C3H7OH–C3H7OH

3.4

14.2

Heat capacity

1961MAT/MCK

iso-C3H7OH– iso-C3H7OH

(1) 4.5 (2) 5.3 (3) 4.1G0.9

18.8 (1) Heat capacity 22.2 (2) Heat capacity 17.2G3.8 (3) TC

16.3 13.47G1.46

(1) Review (2) TR-IR-UV

(1) 2002MON/DIM(b) (2) 2002KAY/EBA

(1) PVT (2) TC

(1) 1968AND/KUD (2) 1978FRU/CUR

(1) Vapor density (2) IR

(1) 1966LIN/CHR (2) 1977GER/TOK

(1) 1963HAL/COX (2) 1964BER/LAR (3) 1981FRU/CUR (continued)

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

1254

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.1 (continued) BDEs in Oxygen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

sec-C4H9OH– sec-C4H9OH

5.25

22.0

Heat capacity

1962BEY/MCK

tert-C4H9OH– tert-C4H9OH

(1) 4.6 (2) 4.3G0.9

19.2 17.8G3.8

(1) Heat capacity (2) TC

(1) 1963BEY/MCK (2) 1981FRU/CUR

H2O(ice, surf.)–C4H9OH 16.2G0.9 17.1G1.6 –C5H11OH –C5H11CHO 15.5G1.4

67.8G3.8 71.5G6.7 64.9G5.9

EI MS

2002SOK/ABB

H2O(ice, surf.)–C4N2

42G5

TPD

2005GUE/TAM

H2O(ice, surf.)–PAN 7.2G0.3 PANZCH3C(O)OONO2

30G1.2

CL

2002RAU/EIC

CF3COOH– cyclopentanone

11.7G1

49.0G4

Vapor density

1966LIN/CHR

1-C8H17OH–C8H18

!6.5, at 0 K

!27.2

IR

2005PAO/SAS

O2–C6H6

1.6G0.3, at 0 K

6.7G1.3

PI

1992GRO/HAG

CO–C6H6

0.60, at 0 K

2.52

Spectroscopy

1995BET/BET

H2O–C6H6

(1) 1.63–2.78, 0 K 6.8–11.6 (2) 2.25G0.28 9.44G1.2 (3) 2.44G0.09 10.23G0.39

(1) Multi-PI (2) PI (3) R2PI

(1) 1992GOT/ZWI (2) 1995CHE/GRO (3) 1998COU/MON(b)

10.0G1.2

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

D2O–C6H6

Phenol–C6H6 –C6D6

O2–C6F6

H2O–p-F-C6H4F

2.67G0.11

11.17G0.48

5.07G0.07, at 0 K 21.21G0.29 5.08G0.06 21.25G0.25

2.1G0.4, at 0 K

8.8G1.7

2.79G0.03, at 0 K 11.66G0.13

1255

R2PI

1998COU/MON(b)

SEP-R2PI

1997WIC/DRO

PI

1992GRO/HAG

R2PI

1995BRE/BAR

H2O–C6H5CH3

2.5G0.1, at 0 K

10.6G0.4

IR PD

2004MIY/FUJ

H2O–naphthalene –azulene

w3.0, at 0 K w25.6

w12.5 w107

PES

2000SCH/KNO

H2O–C6H5OH

(1) 5.60G0.11 23.43G0.46 (2) 5.48 22.90

(1) PES (2) MATI

(1) 1998COU/MON (2) 2000BRA/MEH

Phenol–phenol

6.0, at 0 K

25.1

TR-IR-UV

2004KAY/EBA

H2O–M

1.29G0.0.31, at 0 K 2.00G0.0.31 4.03G0.0.31

5.38G1.32 R2PI

S-(C)-s-C4H9OH–M R-(K)-s-C4H9OH–M MZR-(C)-1-Ph-1C2H4OH

2-C3H7OH–M n-C4H9OH–M S-(C)-s-C4H9OH–M R-(K)-s-C4H9OH–M S-(C)-s-C5H11OH–M R-(K)-s-C5H11OH–M MZR-(C)-1-Ph-1C3H6OH

3.7G0.2, at 0 K 2.6G0.2 4.8G0.2 5.9G0.2 3.1G0.2 4.7G0.2

2000MON/PIU

8.37G1.32 16.87G1.32

15.3G1.0 10.9G1.0 20.2G1.0 24.5G1.0 13.2G1.0 19.6G1.0

R2PI

2000LAT/SAT

(continued)

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

1256

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.1 (continued) BDEs in Oxygen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) H2O–NH(C6H5)(CHO)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

5.65G0.30, at 0 K 5.4G0.3

23.64G1.25

D2O–d1K1-naphthol

(1) 5.82G0.20, 0K (2) 5.82G0.20 (3) 5.83G0.14

H2O–(trans-1-naphthol)

5.8G0.2, at 0 K

24.3G0.8

H2O–C6H5OCH3

3.69G0.11, at 0 K

CO–carbazole

2.05, at 0 K

CO–pyrrole

Methods (reference in parentheses)

References

PES-TOF

2001MON/DIM

24.34G0.83

(1) SEP-R2PI

(1) 1995BUR/DRO

24.34G0.83 24.39G0.59

(2) MATI (3) Supersonic tech.

(2) 2003BRA/NEU (3) 2002WIC/HEN

MATI

2003BRA/NEU

PI

2002MON/DIM(b)

8.57

SEP-R2PI

1995BUR/DRO(b)

0.84, at 0 K

3.50

Spectroscopy

1995BET/BET

ZnO(0001, surf.)/ O–pyridine

13.6

57

TDS

2000HOV/KOL

H2O–indole

(1) 4.67G0.04, 19.52G0.18 0K (2) 4.84G0.23 20.25G0.96

(1) MATI

(1) 1998BRA/GRE

(2) DELFINE

(2) 2000BRA/MEH

Review

2002MON/DIM(b)

DELFINE

1999MON/DIM

H2O–(CHO)C6H5NH

H2O–1-naphthol

CH3OH–indole

5.60G0.37, at 0 K

H2O–1-methyl-indole

4.1G0.1, at 0 K

22.6G1.3

15.44G0.46

23.43G1.55

17.2G0.4

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

H2O–3-methyl-indole

4.49G0.06, at 0 K

18.80G0.24

1257

MATI

2004GEO/NEU

H2O–L (air–water interface) LZNH3 CH3NH2 (CH3)2NH (CH3)3N

9.8G1.2 6.7G0.7 8.1G0.7 8.8G0.7

41G5 28G3 34G3 37G3

Combined

2000MME/HIC

H2O–eugenol 2H2O–eugenol

4.81, at 0 K 5.52

20.11 23.09

REMPI

2004LON/UNA

CO2–perylene

3.56, at 0 K

14.89

Spectra

1993WIT/TOP

1-Naphthol–ethanol –oxirane –oxetane

7.94G0.02 7.71G0.14 O8.17

33.22G0.08 32.26G0.59 O34.18

Supersonic tech.

2002WIC/HEN

CH3OH–CH3NH2 –(CH3)2NH

5.59G0.2 6.19G0.2

23.4G0.8 25.9G0.8

PVT

1974MIL/MIN

CH3OH–N(CH3)3

(1) (2) (3) (4)

24.3G2.9 29.7G0.8 28.9G0.8 14.1G2.4

(1) NMR (2) IR (3) PVT (4) FT-MW

(1) (2) (3) (4)

CH3OH–(CH3)2NC(O)H 7.6G0.3

31.8G1.3

Derived

2006BIR/HUA

CH3OH–(C2H5)3NH

7.3

30.5

Vapor density

1976TUC/LIP

CH3OH–N(C2H5)3

(1) 8.2 (2) 7.5G0.5

34.3 31.4G2.1

(1) IR (2) PVT

(1) 1966HIR/KOZ (2) 1974MIL/MIN

5.8G0.7 7.10G0.2 6.91G0.2 3.4G0.6

1969CLA/GOV 1970FIL/SWI 1974MIL/MIN 1996TAN/IOA

(continued)

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

1258

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.1 (continued) BDEs in Oxygen Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(CF3)2CDOD–N(C2H5)3 (CF3)2CDOD– NEt(I–Pr)2

6.5 6.4

27.2 26.8

Calorimetry

2003MAI/CAR

(CF3)2CDOD– N(C6H5)(CH3)2

2.0

8.4

Calorimetry

2003MAI/CAR

3.3

13.8

Calorimetry

2003MAI/CAR

7.4

31.0

SEP-R2PI

1997WIC/DRO

R2PI

2001BAR/ZEH

(CF3)2CDOD–L LZN-methyl morpholine Quinuclidine

Phenol–cyclo-C6H12

Chiral complexes (R)-2-naphthl-1ethanol–(R)-butan2-ol (R)-2-naphthl-1ethanol–(S)-butan2-ol (R)-2-naphthl-1ethanol–((S)-butan2-ol)2

6.92G0.03, at 0 K

28.95G0.13

2.0G0.3, at 0 K

8.4G1.3

1.3G0.3

5.4G1.3

3.1G0.3

13.2G1.3

Et2O–GaCl3 –GaBr3 –GaI3

50.7 47.4 33.4

212.1 198.3 139.7

CH2FCH2OH–L CF3CH2OH–L (CF3)2CHOH–L LZCp*Fe(dppe) HdppeZ1,2bis(diphenylphosphino)ethane; Cp*Zh-C5Me5

(1) 4.6G0.4 (1) 5.9G0.4 (2) 6.5G0.4

19.2G1.7 24.7G1.7 27.2G1.7

Thermochemical

Spectra

7366—CHAPTER 26—5/2/2007—12:12—JEBA—15382—XML MODEL B – pp. 1243–1349

1966GRE/SRI

(1) 2003BEL/REV (2) 2005BEL/COL

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1259

26.1.2 Positive oxygen-ion clusters/complexes Table 26.1.2 BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

H2OC–He

0.45, at 0 K

1.9

Combined

2001ROT/DOP

H2OC–Ne

1.36, at 0 K

5.69

Combined

2001DOP/ROT

HCOC–Ne

1.25, at 0 K

5.24

IRPD

1996NIZ/DOP

OC–Ar

(1) 15.7G0.5 (2) 8.1

65.6G1.9 33.8

(1) Scattering (2) ICP MS

(1) 1977DIN/KAR (2) 1994NON/MAT

OC 2 ðArÞx –Ar xZ0 1 2 3 4 5 6 7 N

(1) (1) (1) (1) (1) (1) (1) (1) (2)

13.1 12.9 8.6 7.7 7.4 7.1 6.9 6.8 w6

(1) Review

(1) 1994HIR/YAM

(2) Extrapolate

(2) This volume

OC 4 ðArÞx –Ar xZ0 1 2 3 4 5

2.27 2.16 1.86 1.83 1.80 1.78

9.5 9.0 7.8 7.7 7.5 7.4

Review

1994HIR/YAM

OC 6 ðArÞx –Ar xZ0 1

1.98 1.89

8.3 7.9

Review

1994HIR/YAM

3.14 3.08 2.06 1.83 1.76 1.69 1.64 1.62 w1.5

(continued)

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

1260

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 2 3 4

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol 1.70 1.68 1.68

Methods (reference in parentheses)

kJ/mol

References

7.1 7.0 7.0

COC–Ar

(1) 16–23 67–97 (2) 23.9G3.5 100.2G14.5

(1) PIPECO (2) TPEPICO

(1) 1989NOR/GUO (2) 1997MAH/BAU

COC 2 –Ar

(1) 6.0, at 0 K 25.1 (2) 4.6G0.9 19.3G3.9

PI

(1) 1983PRA/DEH (2) 1985DEH

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

(1) PD

H2OC(Ar)x–Ar xZ0 1 2 3 4 5 6 7 8 9 N

4.0–8.0 4.0–8.0 3.1–4.3 3.1–4.3 1.7–2.1 1.7–2.1 1.7–2.1 1.7–2.1 1.7–2.1 1.7–2.1 w1.5

16.7–33.5 16.7–33.5 13.0–18.0 13.0–18.0 7.1–8.8 7.1–8.8 7.1–8.8 7.1–8.8 7.1–8.8 7.1–8.8 w6

(1) 2000DOP/ROT

(2) Extrapolate

(2) This volume

(1) 1.530, 6.40 at 0 K (2) 1.92G0.40 8.01G1.67

(1) MATI

(1) 1999DES/HAI

(2) IR PD

(2) 2001SOL/DOP

(C6H5OH)HC–Ar, p-bond (C6H5OH)HC–Ar, s-bond

1.72G0.29 7.18G1.20

IR PD

2004SOL/DOP(c)

(C6H5OH2)C–Ar, p-bond (C6H5OH2)C–Ar, s-bond

1.86G0.57, 7.78G2.39 at 0 K 3.29G0.86 13.76G3.59

IR PD

2004SOL/DOP(c)

(C6H5OH)C–Ar, p-bond (C6H5OH)C–Ar, s-bond

1.86G0.43 7.78G1.79

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1261

Dibenzo-p-dioxinC–Ar

2.05, at 0 K

8.58

Spectroscopy

1995GRE/NEU

(C10H9OH)C–Ar, s-bond

1.86G0.43

7.78G1.79

IR PD

2004AND/SOL

OC 2 –Kr

7.6

31.8

Photofrag.

1984JAR/MIS

H2OC–Kr

7.6G2.3

31.8G9.6

Photodissociation

1990KIM/KUO

COC 2 –Kr

(1) 17.1, at 0 K 71.5 (2) 10.8G1.2 45.3G4.8

PI

(1) 1985JAR/ILL (2) 1985DEH

Dibenzo-p-dioxinC–Kr

2.62, at 0 K

Spectroscopy

1995GRE/NEU

(1) Spectroscopy (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

Derived from DfH0 in ref.

1998LIA/BAR

OC–H

10.98

(1) 118.3 494.8 (2) 116.61G0.08 487.90G0.34

HOC–H

128.2

536.4

H2OC–H

144.1

602.9

OC–F

(1) w80 (2) 72.1G2.0

w335 301.8G8.4

(1) Review (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

OC 2 –F

9.2

38.6

MS

1966MAL/MCG

FCOC–F

41.2G2

172.6G8

Derived from DfH0 in ref.

1996ASH/APP

(1) Derived (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

OC–O

(1) 154.5 646.6 (2) 154.82G0.07 647.75G0.17

(continued)

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

1262

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(FO)C–O

119.9

501.7

MS

1966MAL/MCG

OC–N

(1) 251.11G 0.04 (2) 251.11G 0.03

1050.64G 0.17 1050.64G 0.13

(1) Derived

(1) 1974GUR/KAR

(2) Derived from IP in ref.

(2) 1996NIST

12.5

52.3

HP MS

1979HIR/SAL

4.0

16.7

(H3O)C–H2

3.5G0.5

14.6G2.1

Scattering

1990OKU/YEH

(HCO)C–H2

3.9

16.3

HP MS

1975HIR/KEB

HC(O2)x–H2 xZ0 1

OC(O2)x–O2 xZ0

1 2

OC 2 ðO2 Þx –O2 xZ0

1 2

(1) (2) (3) (1) (1)

48.0 49.9 42.9 6.9 0.9

200.7 208.9 179.5 28.9 3.9

(1) PI (2) PD (3) PD

(1) 1981LIN/ONO(b) (2) 1981MOS/OZE (3) 1982HIL/VES

(1) (2) (3) (4) (5) (3) (5) (3)

9.6 9.5 10.8 9.7 9.15G0.5 6.87 5.89G0.3 2.54

40.2 39.7 45.2 40.5 38.3G2.1 28.7 24.6G1.3 10.6

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

MS HP MS MS PI HP MS

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

1964YAN/CON 1969DUR/KEB 1970CON/JAN 1981LIN/ONO 1988HIR

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

3 4 5 6 7 N

(HO2)C(O2)x–O2 xZ0 1 2 3 4 5 6 7 8 N

1263

(5) (3) (5) (3) (5) (5) (5) (5) (6)

2.48G0.2 2.46 2.14G0.2 1.84 1.92G0.2 1.89G0.3 1.85G0.4 w1.82 w1.6

10.4G0.8 10.3 9.0G0.8 7.7 8.0G0.8 7.9G1.3 7.7G1.7 w7.6 w6.8

(1) (1) (2) (1) (2) (2) (2) (2) (2) (2) (2) (3)

20.0 6.6 6.87 w3.2 2.66 2.52 2.17 1.96 1.95 1.81 1.72 w1.6

83.7 27.6 28.7 w13.4 11.1 10.5 9.1 8.2 8.2 7.6 7.2 w6.8

(3) Extrapolate

(3) This volume

(6) Extrapolate

(6) This volume

HP MS

(1) 1979HIR/SAL (2) 1989HIR/MOR(e)

PhenolC–CO

6.93G0.03, at 0 K

29.00G0.13

MATI

1999HAI/DES

(H3O)C–OH

12.0G2.8

50.2G11.6

PI MS

1988TOM

OC–N2

55.3

231.4

Review

1986KEE/CAS

(1) (2) (3) (4) (2) (3) (2) (3) (3) (3) (3) (3)

23.8 21.8 20.9G1.3 22.6 18.0 18.8G1.3 14.6 17.6G1.3 16.7G1.3 11.3 10.3 9.5

(1) (2) (3) (4)

(1) (2) (3) (4)

OC 2 ðN2 Þx –N2 xZ0

1 2 3 4 5 6

5.69 5.2 5.0G0.3 5.4 4.3 4.5G0.3 3.5 4.2G0.3 4.0G0.3 2.71 2.45 2.26

MS HP MS HP MS Review

1967JAN/CON 1983SPE/FIT 1988HIR/NAK 2000SIE/GRE

(continued)

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

1264

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 7 8 9 10 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (3) (3) (3) (3) (5)

2.11 1.86 1.68 1.35 w1.3

kJ/mol 8.8 7.8 7.0 5.6 w5.6

Methods (reference in parentheses)

References

(5) Extrapolate

(5) This volume

(H3O)C(H2O)x–N2 xZ1 2

5.3G0.5 5.0G0.5

22.2G2.1 20.9G2.1

Diffusion tube

1987GHE/FIT

(H3O)C(N2)(H2O)x–N2 xZ1 2 3

4.9G1 5.2G1 4.4G1.3

20.5G4.2 21.8G4.2 18.4G5.4

Diffusion tube

1987GHE/FIT

(H3O)C(N2)2(H2O)x–N2 xZ1 2 3

7.8G2 9.0G2.7 w1.2

32.6G8.4 37.7G11.3 w5

Diffusion tube

1987GHE/FIT

(H3O)C(N2)3(H2O)2–N2

w3

w12.6

Diffusion tube

1987GHE/FIT

OC 4 –N2

2.94

12.3

Review

1986KEE/CAS

(C6H5OH)C–N2 4.72, at 0 K (C6H5OH)C–N2, p-bond 2.14G0.43, 0 K

19.7 8.97G1.79

MATI IR PD

1998HAI/GEP 2001SOL/DOP

(C6H5OH)C–N2, s-bond (1) 4.72, at 0 K (2) 4.69G0.03

19.7 19.62G0.12

MATI

(1) 1998HAT/GEP (2) 1999HAI/DES

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

(C6H5OH)HC–N2, p-bond (C6H5OH)HC–N2, s-bond

1265

2.14G0.43, 8.97G1.79 at 0 K 3.72G1.00, at 15.55G4.18 0K

IR PD

2004SOL/DOP(c)

(C6H5OH2)C–N2, p-bond 2.72G0.43, at 11.36G1.79 0K (C6H5OH2)C–N2, s-bond 9.72G0.43, at 40.67G1.79 0K

IR PD

2004SOL/DOP(c)

(C10H9OH)C–Ar, p-bond

1.86G0.43, at 7.78G1.79 0K 3.57G2.14, at 14.95G8.97 0K

IR PD

2004AND/SOL

OC 2 ðCOÞx –CO xZ1 2 3 4 5 6 7 8 9 10 11 12 13 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

7.6 7.5 7.3 3.5 3.4 3.4 3.3 2.4 2.3 2.3 2.3 2.3 2.3 w1.8

31.8 31.4 30.5 14.6 14.2 14.2 13.8 10.0 9.6 9.6 9.6 9.6 9.6 w7.5

(1) Equilibrium

(1) 2003HIR/KAT

(2) Extrapolate

(2) This volume

(HCO)C(CO)x–CO xZ1 2 3 4 5 6 7 8 9 10 11

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1)

4.89 4.66 4.46 4.24 2.39 2.27 2.20 2.11 2.00 1.96 1.89

20.5 19.5 18.7 17.7 10.0 9.5 9.2 8.8 8.4 8.2 7.9

(1) Review

(1) 1994HIR/YAM

(C10H9OH)C–Ar, s-bond

(continued)

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

1266

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 12 13 N

OC 2 ðCO2 Þx –CO2 xZ0 1 2 3 4 5 N

COC 2 ðCO2 Þx –CO2 xZ0

1

2

3 4 5 N (H3O)C(CO2)x–CO2 xZ0 1 2 3

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) Extrapolate

(2) This volume

(1) 1.84 (1) 1.79 (2) w1.8

7.7 7.5 w7.5

(1) (1) (1) (1) (1) (1) (2)

9.8G0.5 8.6G0.5 6.2G0.3 5.1G0.3 4.5G0.5 w4.0 w5.7

41.0G2.1 36.0G2.1 25.9G1.3 21.3G1.3 18.8G2.1 w16.7 w24

(1) HP MS

(1) 1988HIR/NAK

(2) Extrapolate

(2) This volume

(1) (2) (3) (4) (5) (1) (2) (4) (5) (2) (4) (5) (4) (4) (4) (6)

16.2 11.8 15.8 15.6G1.0 16.8 6.0 3.3 5.6G0.3 8.3 2.8 5.1G0.3 6.0 4.8G0.3 4.3G0.4 w4.0 w5.7

67.8 49.4 66.1 65.3G4 70.3 25.1 13.8 23.4G1.3 34.7 11.7 21.3G1.3 25.1 20.1G1.3 18.0G1.7 w16.7 w24

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

(6) Extrapolate

(6) This volume

(1) (2) (2) (2) (3)

14.4 15.3 12.4 10.5 4.3

60.2 64.0 51.9 43.9 18.0

HP MS

(1) 1977MEO/FIE(b) (2) 1986HIR/SHO

HP MS PI HP MS HP MS EI

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

1977MEO/FIE 1981LIN/NG 1982HEA/MAS 1994HIR/YAM 1994CAM/AIT

(3) 1994HIR/YAM

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

(HCO)C(CO2)x–CO2 xZ0 1 2 3 N

(1) (1) (1) (1) (2)

12.6 7.2 6.9 w6.2 w5.7

52.7 30.1 28.9 w26 w24

(HCO2)C(CO2)x–CO2 xZ0 1 2 N

(1) (1) (1) (2)

18.0 6.9 5.9 w5.7

75.3 28.9 24.7 w24

(1) (2) (2) (2) (2) (2) (2) (2) (3)

10.7 13.4G1.0 7.5G0.2 5.9G0.2 5.2G0.2 4.8G0.2 4.3G0.2 3.9G0.2 w4

44.8 56.1G4 31.4G0.8 24.7G0.8 21.8G0.8 20.1G0.8 18.0G0.8 16.3G0.8 w16

OC 2 ðON2 Þx –ON2 xZ0 1 2 3 4 5 6 N

1267

(1) Review

(1) 1994HIR/YAM

(2) Extrapolate

(2) This volume

(1) Review

(1) 1994HIR/YAM

(2) Extrapolate

(2) This volume

HP MS

(1) 1988ILL (2) 1994HIR/FUJ

(3) Extrapolate

(3) This volume

(H2O)C–ON2

24.0G1.4

100.3G5.8

CID

1997BAS/DRE

(H3O)C(ON2)x–ON2 xZ0 1 2 3

16.9G1.5 12.1G0.5 10.2G0.5 w5.2

70.7G6.5 50.6G2.1 42.7G2.1 w22

HP MS

1994HIR/FUJ

OC 3 –O3

16.1G9.2

67.5G39

EI

2002PRO/HER

OClOC–OClO

58.8G11.5

246G48

EI

2002PRO/HER

Cl2OC–OCl2

16.4G6.9

68.5G28.9

EI

2002HAN/FED (continued)

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

1268

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(H3O)C(HCN)x–HCN xZ0 1 2

32.3 18.8 13.2

135 78.7 55.2

HP MS

1986KEE/CAS

(L)HC–HCN LZH2C(O) CH3OH CH3C(O)H (CH3)2C(O) C2H5C(O)OCH3 (c-C3H5)2C(O)

27.0 25.7 23.0 20.4 19.0 17.6

113 108 96.2 85.4 79.5 73.6

HP MS

1985SPE/MEO

(L)HC–HCN LZHC(O)NH2 CH3C(O)N(CH3)2

19.3 15.8

80.8 66.1

HP MS

1985SPE/MEO

OC 2 –H2O

O16

O67

FA

1970ADA/BOH

(OH)C(H2O)x–H2O xZ2 3 4 5 6 7 8 9 N

(1) (1) (1) (1) (1) (1) (1) (1) (2)

87.4 75.3 53.6 51.0 44.4 41.8 42.7 42.7 w44

(1) QP MS

(1) 2003FRO/LOV(b)

(2) Extrapolate

(2) This volume

(OH)C(H2SO4)(H2O)x– H2O xZ4 5 6

(1) 13.6 (1) 11.9 (1) 10.7

(1) QP MS

(1) 2003FRO/LOV(b)

20.9 18.0 12.8 12.2 10.6 10.0 10.2 10.2 w10.5

56.9 49.8 44.8

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

7 8 9 10 11 12 13 N

(1) (1) (1) (1) (1) (1) (1) (2)

10.9 11.6 11.3 11.3 11.6 10.7 10.5 w10.5

45.6 48.5 47.3 47.3 48.5 44.8 43.9 w44

(OH)C(H2SO4)2(H2O)x– H2O xZ4 5 6 7 8 9 10 11 12 13 14 N

(1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (1) (2)

13.6 12.1 11.3 11.8 12.0 11.7 11.9 11.6 11.6 11.3 10.5 w10.5

56.9 50.6 47.3 49.4 50.2 49.0 49.8 48.5 48.5 47.3 43.9 w44

(OH)C(H2SO4)3(H2O)x– H2O xZ5 6 7 8 9 N

(1) (1) (1) (1) (1) (2)

12.1 12.3 12.5 12.1 12.1 w10.5

50.6 51.5 52.3 50.6 50.6 w44

(H2O)C–H2O

(H3O)C(H2O)x–H2O xZ0

1269

(2) Extrapolate

(2) This volume

(1) QP MS

(1) 2003FRO/LOV(b)

(2) Extrapolate

(2) This volume

(1) QP MS

(1) 2003FRO/LOV(b)

(2) Extrapolate

(2) This volume

(1) 36.4G3.0 (2) 39.2

152.4G12.6 164.0

PES

(1) 1977NG/TRE (2) 1982TOM/ACH

(1) (2) (3) (4) (5)

146G6 140.2 157G8 150.6 132G7

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

35.0G1.5 33.5 37.4G1.8 36.0 31.5G1.7

HP MS Review GIB MS HP MS GIB MS

1986HIR/TAK 1992MEO 1993HON/SUN 1997KEB/SEA 2004HON/ARM (continued)

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

1270

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 1

2

3

4

5

6

7

8

9 10 11

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) 20.2G1.5 (2) 20.8 (3) 22.2G0.8 (4) 22.3 (6) 20.9 (2) 17.4 (3) 17.9G0.5 (4) 17.0 (7) 17.9 (8) 17.4 (2) 12.3 (4) 15.3 (6) 12.8 (7) 12.7 (8) 13.9 (1) 11.8 (4) 13.0 (6) 12.2 (7) 11.6 (9) 10.5G0.6 (1) 10.7 (4) 11.7 (6) 10.6 (9) 9.4G0.9 (10) 12.0 (4) 10.3 (6) 10.0 (9) 9.5G0.5 (10) 9.8 (11) 6.7 (6) 10.2 (10) 8.8 (11) 5.1 (6) 10.2 (10) 8.9 (11) 5.7 (10) 9.3 (11) 6.7 (10) 9.8 (11) 6.7 (10) 10.3 (11) 6.9

kJ/mol 85G6 87.0 93G3 93.3 87.4 72.8 74.9G2.1 71.1 74.9 72.8 51.5 64.0 53.6 53.1 58.2 49.4 54.4 51.0 48.5 43.9G2.5 44.8 49.0 44.4 39.3G3.8 50.3 43.1 41.8 39.7G2.1 40.9 28.0 42.7 36.7 21.3 42.7 37.2 23.8 38.9 28.0 41.1 28.0 43.1 28.9

Methods (reference in parentheses)

References

(6) MS

(6) 2003FRO/LOV(b)

(7) Review (8) FT-ICR

(7) 1994HIR/YAM (8) 1994THO/TON

(9) MS

(9) 2003WAN/TSA

(10) TOF MS

(10) 1993SHI/FOR

(11) CID

(11) 1991MAG/DAV

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

12

(10) 10.6 (11) 6.7 (10) 10.7 (11) 6.8 (10) 10.8 (11) 6.7 (10) 10.8 (11) 6.0 (10) 10.8 (11) 6.6 (10) 10.7 (11) 6.3 (10) 10.5 (11) 7.0 (10) 10.4 (11) 9.1 (10) 10.3 (11) 7.3 (10) 10.5 (11) 5.9 (10) 10.3 (11) 6.4 (10) 10.1 (11) 6.6 (10) 9.7 (11) 7.1 (10) 9.4 (11) 6.3 (10) 9.1 (11) 8.2 (12) w10.5

44.4 28.0 44.9 28.5 45.3 28.0 45.0 25.1 45.0 27.6 44.6 26.4 44.1 29.3 43.6 38.1 43.2 30.5 43.7 24.7 43.0 26.8 42.1 27.6 40.7 29.7 39.4 26.4 37.9 34.3 w44

31.5G2.6 19.6G0.5 15.8G0.2

(H2SH)C–H2O

(CH2CO)C–H2O

13 14 15 16 17 18 19 20 21 22 23 24 25 26 N

(D3O)C(D2O)x–D2O xZ0 1 2

1271

(12) Extrapolate

(12) This volume

132G11 82G2 66G1

CID

2004HON/ARM

(1) 17.0 (2) 21

71.1 88

HP MS

(1) 1977MEO/FIE (2) 1977HIR/KEB

11.6

48.5

EI

1986POS/RUT (continued)

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

1272

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) (H2CO)HC(H2O)x–H2O xZ0

1 2 3 4 5 6 N

(HCOOH)HC–H2O

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (2) (3) (4) (1) (4) (1) (4) (4) (4) (4) (4) (5)

24.1

(CH3OH)HC(H2O)x–H2O xZ0 (1) (2) 1 (1) (2) 2 (1) (2) 3 (1) (2) 4 (1) (2) 5 (1) (2) 6 (2) N (3)

(RSH)HC–H2O RZMe Et n-Pr i-Pr

26.8 26.5 27.9 27.7 18.5 21.5 17.0 17.6 12.9 11.1 9.5 10.0 w10.5

25.4 27.6 21.0 19.8 14.8 14.1 11.6 11.6 9.1 9.8 9.4 8.9 8.9 w10.5

15.5 14.7 14.4 13.9

kJ/mol

Methods (reference in parentheses) FA ICR ICR HP MS

References

112.1 110.9 116.7 115.9 77.4 90.0 71.1 73.6 54.0 46.4 39.7 41.8 w44

(1) (2) (3) (4)

(5) Extrapolate

(5) This volume

100.8

HP MS

1984MEO(b)

106.3 115.6 87.9 82.8 61.9 59.0 48.5 48.5 38.1 41.0 39.3 37.2 37.2 w44

HP MS

(1) 1984MEO (2) 1986HIR/TAK

(3) Extrapolate

(3) This volume

64.9 61.5 60.2 58.2

HP MS

1985MEO/SIE

7366—CHAPTER 26—5/2/2007—12:14—JEBA—15382—XML MODEL B – pp. 1243–1349

(1) (2) (3) (4)

1978FEH/DOT 1980BER/BEA 1982LAR/MCM 1984MEO

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1273

(CH3OH)2HC(H2O)x– H2O xZ2 3 4

11.2 10.4 w9.4

46.9 43.5 w39

HP MS

1973GRI/KEB

(CH3OH)3HC(H2O)x– H2O xZ1 2 3

11.8 9.2 w9.3

49.4 38.5 w39

HP MS

1973GRI/KEB

(CH3OH)4HC(H2O)x– H2O xZ0 1 2

12.1 8.6 w9.1

50.6 36.0 w38

HP MS

1986MEO

(CH3OH)5HC–H2O

10.0

41.8

HP MS

1986MEO

(1) (2) (1) (2) (1) (2) (1) (2) (2) (1) (3)

100.4 110.9 80.3 78.2 59.4 56.1 52.3 47.3 40.6 54.8 w44

HP MS

(1) 1977KEB (2) 1986HIR/TAK

(3) Extrapolate

(3) This volume

(C2H5OH)HC(H2O)x– H2O xZ0 1 2 3 4 5 N

24 26.5 19.2 18.7 14.2 13.4 12.5 11.3 9.7 13.1 w10.5

(CHF2CH2OH)HC–H2O

30

126

ICR

1986KEE/CAS

(n-C3H7OH)HC(H2O)x– H2O xZ0 1

(1) 23.9 (1) 17.9

100 74.9

(1) HP MS

(1) 1986HIR/TAK (continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

1274

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 2 3 4 5 N

(i-C3H7OH)HC(H2O)x– H2O xZ0 1 2 3 4 5 6 N

(CH3CO)C(H2O)x–H2O xZ0 1 2 3 4 5 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) Extrapolate

(2) This volume

(1) HP MS

(1) 1986HIR/TAK

(2) Extrapolate

(2) This volume

(1) (1) (1) (1) (2)

13.0 11.0 9.5 8.8 w10.5

54.4 46.0 39.7 36.8 w44

(1) (1) (1) (1) (1) (1) (1) (2)

16.3 16.4 12.5 10.5 9.6 8.8 w7.9 w10.5

68.2 68.6 52.3 43.9 40.2 36.8 w33 w44

(1) (2) (3) (3) (3) (3) (3) (4)

24.6 21.9 20.1 17.8 12.9 10.8 w10.3 w10.5

102.9 91.6 84.1 74.5 54.0 45.2 w43 w44

HP MS

(1) 1978DAV/LAU (2) 1979DAV/SUN (3) 1984MEO(b)

(4) Extrapolate

(4) This volume

(CF3CH2OH)HC–H2O

31.1

130.1

ICR

1982LAR/MCM

(CH3CHO)HC(H2O)x– H2O xZ0 1 2 3 4 5

(1) (1) (1) (1) (1) (1)

104.6 70.3 71.1 47.3 39.3 38.9

(1) HP MS

(1) 1984MEO(b)

25.0 16.8 17.0 11.3 9.4 9.3

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

6 N

1275

(1) 9.8 (2) w10.5

41.0 w44

(2) Extrapolate

(2) This volume

(CF3COOH)HC–H2O

28.6

119.7

ICR

1982LAR/MCM

(CH3OCHO)HC(H2O)x– H2O xZ0 1 2 3 N

(1) (1) (1) (1) (2)

21.5 16.2 13.6 w11.0 w10.5

90.0 67.8 56.9 w46 w44

(1) HP MS

(1) 1984MEO(b)

(2) Extrapolate

(2) This volume

(1) (2) (3) (1) (3) (4) (1) (3) (4) (1) (5)

22.6 24.0 23.9 15.3 15.3 16.7 13.8 13.9 12.9 10.2 w10.5

94.6 100.4 100 64.0 64 69.9 57.7 58 54.0 42.7 w44

(1) HP MS (2) HP MS (3) CID

(1) 1974HIR/GRI (2) 1984MEO(b) (3) 2006GOE/CHE

(4) FT-ICR

(4) 1994THO/TON

(5) Extrapolate

(5) This volume

(CH3)2OHC(H2O)x–H2O xZ0

1

2

3 N

CH3CHCOCH3–H2O

11.2

46.9

HP MS

1986KEE/CAS

(CH3)2SHC(H2O)x–H2O xZ0 1

13.1 11.6

54.8 48.5

HP MS

1985MEO/SIE

(R1R2S)HC–H2O R1 R2 Me Et n-Pr n-Pr

12.6 12.2

52.7 51.0

HP MS

1985MEO/SIE

(C2H5CO)C(H2O)x–H2O xZ0

(1) 23.7

99.2

(1) HP MS

(1) 1979DAV/MEZ (continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

1276

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 2 3 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(2) 16.4 (2) 12.7 (3) w10.5

68.6 53.1 w44

((CH3)2CO)HC(H2O)x– H2O xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

20.5 13.6 12.7 10.3 10.3 w10.5

85.8 56.9 53.1 43.1 43.1 w44

((CH3)2CO)2HC(H2O)x– H2O xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

11.7 13.8 10.9 8.9 8.6 w10.5

49.0 57.7 45.6 37.2 36.0 w44

((CH3)3CO)3HC(H2O)x– H2O xZ0 1 2 3 N

(1) (1) (1) (1) (2)

18.7 9.7 8.2 8.6 w10.5

78.2 40.6 34.3 36.0 w44

(CH3COOH)HC(H2O)x– H2O xZ0 1 2

(1) 20.4 (1) 17.8 (1) 12.9

85.4 74.5 54.0

Methods (reference in parentheses)

References

(2) HP MS

(2) 1986KEE/CAS

(3) Extrapolate

(3) This volume

(1) HP MS

(1) 1984MEO(b)

(2) Extrapolate

(2) This volume

(1) Review

(1) 1998MEO/SCH

(2) Extrapolate

(2) This volume

(1) Review

(1) 1998MEO/SCH

(2) Extrapolate

(2) This volume

(1) Review

(1) 1999MEO/ELM

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

3 N

(1) 10.8 (2) w10.5

45.2 w44

(CH3COOH)2HC(H2O)x –H2O xZ0 1 2 N

(1) (1) (1) (2)

61.9 51.9 42.8 w44

(CH3COOH)3HC(H2O)x –H2O xZ0 1

11.5 10.4

1277

(2) Extrapolate

(2) This volume

(1) Review

(1) 1999MEO/ELM

(2) Extrapolate

(2) This volume

48.1 43.5

Review

1999MEO/ELM

10.9

45.6

Review

1999MEO/ELM

(L)HC–H2O LZCH3COOCHCH2 CH3COOCH2CH3 (CH3)2CH(OCH3)

19.2 20.3 10.8

80.3 84.9 45.2

HP MS

1986KEE/CAS

(L)HC–H2O LZCH3(N(CH3)2)CO (C2H5)2O CH3O(CH2)3OCH3

16.5 20.9 9

69.0 87.4 38

HP MS

1984MEO(b)

(1) (2) (2) (2) (2) (2) (2) (3)

89.1 78.7 55.2 52.3 43.9 42.6 39.3 w44

HP MS

(1) 1984MEO (2) 1994MEO/SIE

(3) Extrapolate

(3) This volume

74.5

HP MS

1984MEO

(CH3COOH)4HC(H2O)– H2O

(n-C3H7)2OHC(H2O)x– H2O xZ0 1 2 3 4 5 N

(i-C3H7)2OHC–H2O

14.8 12.4 10.2 w10.5

21.3 18.8 13.2 12.5 10.5 10.2 9.4 w10.5

17.8

(continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

1278

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

(1,2-propanediol) HC(H2O)x–H2O xZ0 1 2 N

(1) (1) (1) (2)

(1,3-propanediol) HC(H2O)x–H2O xZ0 1 2

References

68.6 56.1G1.7 45.6G1.7 w44

(1) EI-HP MS

(1) 2004GIL/VIE

(2) Extrapolate

(2) This volume

14.6G1.1 12.6G0.6 13.6G0.5

61.1G4.6 52.7G2.5 56.9G2.1

EI-HP MS

2004GIL/VIE

(1,3-butanediol) HC(H2O)x–H2O xZ1 2

11.6G0.3 8.9G0.8

48.5G1.3 37.2G3.3

EI-HP MS

2004GIL/VIE

(1,4-butanediol) HC(H2O)x–H2O xZ1 2

12.3G0.5 11.3G0.3

51.5G2.1 47.3G1.3

EI-HP MS

2004GIL/VIE

13.8

57.7

HP MS

1969FIE

(1) (2) (2) (2) (3)

63.2 68.6 65.7 47.3 w44

(1) HP MS (2) HP MS

(1) 1984MEO(b) (2) 1994MEO/SIE

(3) Extrapolate

(3) This volume

73.6

HP MS

1994MEO/SIE

(t-C5H11OOCCH3)HC –H2O

(MeO(CH2)2OMe)HC (H2O)x–H2O xZ0 1 2 N

(Me(OC2H4)2OMe)HC (H2O)x–H2O xZ0

16.4 13.4G0.4 10.9G0.4 w10.5

kJ/mol

Methods (reference in parentheses)

15.1 16.4 15.7 11.3 w10.5

17.6

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1 2

13.1 !10.2

54.8 !42.7

(Me(OC2H4)3OMe)HC (H2O)x–H2O xZ0 1 2 3 N

(1) (1) (1) (1) (2)

20.4 12.3 10.3 9.1 w10.5

85.4 51.5 43.1 38.1 w44

((MeCO)2CH2)HC (H2O)x–H2O xZ0 1 2 3 4 5 N

(1) (1) (1) (1) (1) (1) (2)

15.9 11.2 9.5 9.0 9.7 9.3 w10.5

66.5 46.9 39.7 37.7 40.6 38.9 w44

(MeCO)2C2H4)HC (H2O)x–H2O xZ0 1 2 3 N

(1) (1) (1) (1) (2)

13.0 13.1 10.7 9.7 w10.5

54.4 54.8 44.8 40.6 w44

1279

(1) HP MS

(1) 1994MEO/SIE

(2) Extrapolate

(2) This volume

(1) HP MS

(1) 1998MEO/SCH

(2) Extrapolate

(2) This volume

(1) HP MS

(1) 1998MEO/SCH

(2) Extrapolate

(2) This volume

(MeCOC2H4COMe)2HC –H2O

15.1

63.2

HP MS

1998MEO/SCH

(Me(OC2H4)2OMe)2HC –H2O

20.6

86.2

HP MS

1996MEO/SIE

(C6H13)2OHC–H2O

18.2

76.1

HP MS

1985MEO(b)

103.8G4.2

(1) HP MS

(1) 1986DEA/MEO

(CH3CN)HC(H2O)x–H2O xZ0 (1) 24.8G1

(continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

1280

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 1

(CH3CN)2HC(H2O)x– H2O xZ0 1 2 3 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

1 2

References

(2) 22.1G1.4 (1) 17.5G1 (2) 15.0G1.7

92.5G5.9 73.2G4.2 62.8G7.1

(2) GIB MS

(2) 1993HON/SUN

(1) (1) (1) (1) (2)

66.5 64.0 43.1 w41 w44

(1) HP MS

(1) 1986DEA/MEO

(2) Extrapolate

(2) This volume

40.6

HP MS

1986KEE/CAS

68.2 51.9 56.9 59.8 48.5

(1) HP MS (2) FT-ICR

(1) 1974HIR/GRI (2) 1994THO/TON

15.9 15.3 10.3 w9.7 w10.5

(CH3CN)3HC(H2O)–H2O 9.7

((CH3)2O)2HC(H2O)x– H2O xZ0

kJ/mol

Methods (reference in parentheses)

(1) (2) (1) (2) (1)

16.3 12.4 13.6 14.3 11.6

((CH3)2O)3HC(H2O)x– H2O xZ0 1

23.0 11.4

96.2 47.7

HP MS

1974HIR/GRI

(c-C3H5)(CH3)COHC– H2O xZ0 1 2 3 N

(1) (1) (1) (1) (2)

49.4 42.7 41.8 w41 w44

(1) HP MS

(1) 1984MEO(b)

(2) Extrapolate

(2) This volume

11.8 10.2 10.0 w9.7 w10.5

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1281

c-C5H10OHC–H2O (c-C3H5)2OHC–H2O

19.5 16.6

81.6 69.5

HP MS

1984MEO

(c-C3H5)2COHC–H2O xZ0 1 2 3 N

(1) (1) (1) (1) (2)

69.0 46.9 37.2 w38 w44

(1) HP MS

(1) 1984MEO

(2) Extrapolate

(2) This volume

16.5 11.2 8.9 w9.1 w10.5

BHC(H2O)x–H2O BZ tetrahydrofuran (1) 21.8 (2) 19.8 (1) 13.1

91.2 82.8 54.8

HP MS

xZ0 1

(1) 1984MEO(b) (2) 1987HIR/TAK

BHC(H2O)x–H2O, BZ2-methyltetrahydrofuran xZ0 1

18.5 13.1

77.4 54.8

HP MS

1987HIR/TAK

(1) 10.2 (2) 10.4 (1) 9.8

42.7 43.5 41.0

HP MS

(1) 1987HIR/TAK (2) 1988NIC/SUN

78.0G0.6 77.57G0.46 78.0G0.6

(1) TP-ZEKE (2) MATI (3) MATI

(1) 1994DOP/REI (2) 1998COU/MON (3) 2000BRA/MEH

(FuranH)C–H2O FuraneC–H2O

(Phenol)C–H2O

(1) 18.6G0.1 (2) 18.54G0.11 (3) 18.6G0.1

(1-naphthol)C–H2O

15.9

66.4

MATI

2000BRA/MEH

(C6H5)(CH3)COHC–H2O

19.5

81.6

HP MS

1984MEO

(BH)C(H2O)x–H2O BZ1,4-cyclohexanedione xZ0 20.2

84.5

HP MS

1998MEO/SCH (continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

1282

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 1

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

13.6

56.9

(C6H5)(N(CH3)2)COHC– H2O

15.1

63.2

HP MS

1985MEO(c)

(15-crown-5-ether)HC– H2O

(1) 12.8 (2) 21.6

53.6 90.4

HP MS

(1) 1983MEO/SIE (2) 1984SHA/KEB

(18-crown-6-ether)HC– H2O

(1) 26.4 (2) 28.3

110.5 118.4

(1) HP MS (2) FT-ICR

(1) 1984SHA/KEB (2) 1999RYZ/DUN(b)

(p-benzoquinone)HC– H2O

21.5G0.5

90.0G2.3

HP MS

1996IRI/MEO

(BPTIC6HC)6C(H2O)x– H2O xZ0 1 2 BPTIZbovine pancreatic trypsin inhibitor

21.3G1 16 14

89.1G4.2 66.9 58.6

MS

1997WOE/HUD

H2OHC(H2O)–H2S

13.7

57.3

HP MS

1977HIR/KEB

H2OHC(H2S)x–H2S xZ0 1

24.9 13.3

104.2 55.6

HP MS

1977HIR/KEB

H3OC(H2O)x–HC(O)H xZ0

(1) w32

w134

(1) FA

(1) 1978FEH/DOT

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

32.2 32.9 18.9 22.8 16.4 20.9 16.3 14.7 12.6 11.9

124.7 137.7 79.1 95.4 68.6 87.4 68.2 61.5 52.7 49.8

(2) ICR (3) HP MS

(2) 1982LAR/MCM (3) 1984MEO

(1) 27.6 (2) 27.7

115.5 115.9

(1) FA (2) ICR

(1) 1978FEH/DOT (2) 1982LAR/MCM

H3OC(NH3)x–NH3 xZ0 1 2 3

54.8 18.4 17.1 15.0

229.3 77.0 71.5 62.8

HP MS

1986KEE/CAS

H3OC(H2O)(NH3)x–NH3 xZ0 1 2

37.9 18.2 15.7

158.6 76.1 65.7

HP MS

1986KEE/CAS

H3OC(H2O)2(NH3)x–NH3 xZ0 31.8 1 17.3

133.1 72.4

HP MS

1986KEE/CAS

30.4G1.0

127.2G4.2

HP MS

1996MEO/SIE

62.8 37.1 61.9 40.0 40.0

262.8 155.3 258.9 167.3 167.3

Derived

2002BOU/CHO

1 2 3 4 5 6

H2COHC–HC(O)H

(MeOCH2CH2)2OHC– NH3

(BH)C–NH3 BZoxirane acetaldehyde oxetane propanal tetrahydrofurane

(2) (3) (1) (3) (1) (3) (3) (3) (3) (3)

1283

(continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

1284

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) butanal tetrahydropyrane pentanal

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

41.4 37.4 41.8

173.4 156.3 175.0

H3OC–PH3

34.5

144

ICR

1986KEE/CAS

H3OC–SO3

17.7

74

Flow reactor

1999POM/BAC

HOC–OsO3

101G16

423G67

Derived

1989IRI/BEA

(HCOOH)C–HCOOH

23.1G2.3

96.5G9.6

PES

1983TOM/ACH

H3OC(CH4)x–CH4 xZ0 1

8.0 3.4

33.5 14.2

HP MS

1972BEN/FIE(b)

(CH3OH)C–CH3OH

27.7G4.6

115.8G19.3

PES

1983TOM/KIM

(1) (2) (3) (4) (5) (1) (4) (5) (6) (1) (4) (6) (7)

138.5 131.4 134.3 132.2 136.4 110.0 88.7 88.7 115.5 67.4 58.6 82.8 87.9

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

HC(CH3OH)x–CH3OH xZ1

2

3

33.1 31.4 32.1 31.6 32.6 26.3 21.2 21.2 27.6 16.1 14.0 19.8 21.0

HP MS ICR HP MS HP MS Review

1973GRI/KEB 1982LAR/MCM 1986MEO 1992ELS/DAL 1992MEO

(6) HP MS

(6) 1994HIR/YAM

(7) HP MS

(7) 2003RUS/IBR

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

4

5

6 7 N

H3OC(H2O)x(CH3OH)– CH3OH xZ0 1 2 3

(1) (6) (7) (1) (6) (7) (1) (6) (1) (6) (8)

13.5 14.1 14.3 12.5 11.6 11.3 11.9 9.8 12.0 8.9 w8.7

56.5 59.0 59.8 52.3 48.5 47.3 49.8 41.0 50.2 37.2 w37

(1) (1) (2) (2) (2)

24.5 16.4 18.0 14.4 13.2

1285

(8) Extrapolate

(8) This volume

102.5 68.6 75.3 60.2 55.2

HP MS

(1) 1986MEO (2) 1986KEE/CAS

((CH3)2O)HC(CH3OH)x –CH3OH xZ0 1 2 3

26.3 18.8 15.9 13.7

110 78.7 66.5 57.3

HP MS

1974HIR/GRI

((CH3)2O)2HC(CH3OH)x –CH3OH xZ0 1 2

18.1 15.1 12.2

75.7 63.2 51.0

HP MS

1974HIR/GRI

(BH)C–CH3OH BZHC(O)OH CH3CHO C2H5OH

31.8 32.4 29.2

133.1 135.6 122.2

ICR

1982LAR/MCM

CH3CHCOCH3–CH3OH

13.1

54.8

HP MS

1986KEE/CAS (continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

1286

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) (CH3OCH2)2HC(B)x–B BZCH3OH xZ0 1 2 3 4 5 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

(1) HP MS

(1) 1994MEO/SIE

(2) Extrapolate

(2) This volume

19.5

81.6

HP MS

1984SHA/KEB

20.0

83.7

20.0

83.7

20.9 13.9

87.4 58.2

HP MS

1991ELS/OLA

(CH3OH)HC (CH3CN)2–CH3OH

13.7

57.3

HP MS

1991ELS/OLA

(phenol)C–CH3OH

21.40G0.18

89.53G0.75

PES

1998COU/MON

H3OC(H2O)x–CH3CN xZ0 1 2 3 4 5

46.7 32.6 28.7 22.4 20.1 18.6

195.4 136.4 120.1 93.7 84.1 77.8

HP MS

1986KEE/CAS

(CH3OH)xHC (CH3CN)–CH3OH xZ1 2

22.0 14.4 12.6 10.2 9.2 8.9 w8.7

References

92.0 60.2 52.7 42.7 38.5 37.2 w37

C8 H17 OC 4 –CH3OH (12-crown-4-etherHC) C10 H21 OC 5 –CH3OH (15-crown-5-etherHC) C12 H25 OC 6 –CH3OH (18-crown-6-etherHC)

(1) (1) (1) (1) (1) (1) (2)

kJ/mol

Methods (reference in parentheses)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

(CH3CN)HC–CH3CN

126.4G4 124.7G4 130.1G10

(1) HP MS (2) HP MS (3) GIB MS

(1) 1978MEO(b) (2) 1986DEA/MEO (3) 1993HON/SUN

H3OC(CH3CN)x–CH3CN xZ1 23.4 2 20.6

97.9 86.2

HP MS

1986DEA/MEO

H3OC(H2O)(CH3CN)x– CH3CN xZ1 2

21.2 15.0

88.7 62.8

HP MS

1986KEE/CAS

H3OC(H2O)x(CH3CN)– CH3CN xZ2 3

(1) 15.9 (2) 14.4

66.5 60.2

HP MS

(1) 1986KEE/CAS (2) 1986DEA/MEO

(CH3OH)HC(CH3CN)x– CH3CN xZ1 2

22.6 7.0

94.6 29.3

HP MS

1991ELS/OLA

15.6

65.3

HP MS

1991ELS/OLA

R1R2OHC–CH3CN R1 R2 Me Me Et Et n-Pr n-Pr C6H5 MeO

29.9 26.5 25.6 23.4

125.1 110.9 107.1 97.9

HP MS

1985SPE/MEO

(R1R2CO)HC–CH3CN R1 R2 Me Me Me MeO Me EtO

27.7 27.0 25.8

115.9 113.0 107.9

HP MS

1985SPE/MEO

(CH3OH)2HC (CH3CN)–CH3CN

(1) 30.2G1 (2) 29.8G1 (3) 31.1G2.3

1287

(continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

1288

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) Me i-Pr H Me H Me

t-Bu i-Pr MeNH c-C6H11 C6H5 C6H5

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

25.0 23.6 23.1 25.7 25.6 23.2

104.6 98.7 96.7 107.5 107.1 97.1

H3OC–CH3SH

34.5

144.3

ICR

1986KEE/CAS

CH3 OHC 2 –HC(O)OH

29.7

124.3

ICR

1982LAR/MCM

28.6 (AcAlaOCH3)HC– CH3NH2 AcZCH3C(O), AlaZNHCH(CH3)C(O)

119.7

HP MS

1984MEO

HCOC–C2H3

271.3

1135

Derived

1998SCH/BLA

CH2OC–C2H2

279.2

1168

Derived

1998SCH/BLA

(L)HC–CH3C(O)H LZCH3OH CH3C(O)H CH3C(O)OH C2H5OH

34.7 31.9 29.0 31.2

145.2 133.5 121.3 130.5

Review

1996KEE/CAS

(BH)C–CH3C(O)OH BZCH3CHO CH3C(O)OH C2H5OH (CH3)2O

32.5 29.5 31.4 29.3

136.0 123.4 131.4 122.6

Review

1996KEE/CAS

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

HC(B)x–B, BZ CH3C(O)OH xZ1 2

117.6 76.6 77.4 54.8 53.1 50 50.6

Review

14.8 12.4

61.9 51.9

Review

1999MEO/ELM

(B)2(H2O)2HC–B, BZCH3COOH

12.1

50.6

Review

1999MEO/ELM

(N(CH3)2(CH3)COHC– CH3COOH

18.4

77.0

HP MS

1984MEO

(H3O)C–B, BZCF3COOH (CF3COOH)HC–B

33.0

138.1

ICR

1982LAR/MCM

28.9

120.9

(H3O)C(H2O)x–(CH3)2O xZ0 1 2 3

45.4 29.1 23.4 17.9

190.0 121.8 97.9 74.9

HP MS

1974HIR/GRI

HC(CH3OH)x–(CH3)2O xZ1 2 3 4

35.0 21.9 17.2 15.3

146.4 91.6 72.0 64.0

HP MS

1974HIR/GRI

3 4

(B)x(H2O)HC–B, BZCH3COOH xZ1 2

(1) (1) (2) (1) (2) (1) (2)

28.1 18.3 18.5 13.1 12.7 12 12.1

1289

(1) 1992MEO (2) 1999MEO/ELM

(continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

1290

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) (H3O)C((CH3)2O)x– (CH3)2O xZ1 2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(1) 1974HIR/GRI

(2) FT-ICR

(2) 1994THO/TON

68.6 66.1

HP MS

1974HIR/GRI

16.9

70.7

HP MS

1974HIR/GRI

CH3 OHC 2 ((CH3)2O)xK (CH3)2O xZ0 1

35.0 20.2

146.4 84.5

HP MS

1974HIR/GRI

(CH3OH)2HC ((CH3)2O)x–(CH3)2O xZ0 1

21.9 16.6

91.6 69.5

HP MS

1974HIR/GRI

(1) (2) (3) (4) (1)

128.4 123.4 134.3 128.4 42.3

HP MS

(1) (2) (3) (4)

31.1

130.1

Review

1986KEE/CAS

30.2

126.4

(H3O)C(H2O)2 ((CH3)2O)–(CH3)2O

HC((CH3)2O)x–(CH3)2O xZ1

2

(CH3COOH)HC–B, BZ(CH3)2O (C2H5COOH)HC–B

77.4 70.3 90.8

16.4 15.8

References

(1) HP MS

(H3O)C(H2O) ((CH3)2O)x–(CH3)2O xZ1 2

(1) 18.5 (1) 16.8 (2) 21.7

Methods (reference in parentheses)

30.7 29.5 32.1 30.7 10.1

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

1973GRI/KEB 1984MEO 1991MEO/SIE 1992MEO

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

(nC3H7OH)HC–B, BZ(CH3)2O (iC3H7OH)HC–B (1,4-dioxane)HC–B

31.9

133.5

31.9 29.9

133.5 125.1

(CH3CO)C–B, BZ(CH3)2CO (CH3)2COC–B

12.5

52.3

O12.4

O51.9

(1) (2) (3) (4) (5) (4) (6) (4) (6)

125.9 134.3 125.5 125.5 128.4 48.1 51.0 40.8 35.6

(B)xHC–B, BZ(CH3)2CO xZ1

2 3

(B)x(H3O)C–B, BZ(CH3)2CO xZ2 3

30.1 32.1 30.0G0.5 30.0 30.7 11.5 12.2 9.7 8.5

1291

Review

1986KEE/CAS

PI

1978TRO/BLA

(1) (2) (3) (4) (5)

HP MS ICR HP MS HP MS MIKES

(1) (2) (3) (4) (5)

1980LAU/SAL 1982LAR/MCM 1991SZU/MCM 1998MEO/SCH 2005NOR/SOL

(6) HP MS

(6) 1994HIR/YAM

19.1 12.5

79.9 52.3

HP MS

1998MEO/SCH

30.5

128

ICR

1982LAR/MCM

(BH)C–(CH3)2CO BZCH3COOC2H5 c-C4H8O CH3COC2H5 1,4-dioxane (C2H5)2O (C2H5)2CO

30.0 31.0 29.4 32.6 29.3 28.5

125.5 129.7 123.0 136.4 122.6 119.2

Review

1996KEE/CAS

(CH3)2COHC–(CH3)2SO

41.1

172.0

HP MS

1980LAU/SAL

(CH3COOCH3)HC– (CH3)2CO

(continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

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Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(BH)C–C2H5OH BZCH3OH CH3COH CH3COOH n-C3H7H

36.0 32.9 29.5 30.5

150.6 137.7 123.4 127.6

Review

1986KEE/CAS

(BH)C–C2H5OH BZiC3H7OH nC4H9OH

(1) 30.7 (2) 29.8

128.4 1124.7

ICR

(1) 1981BOM/BEA (2) 1982LAR/MCM

(1) (2) (3) (4) (3) (4) (3) (3) (3) (5)

133.9 133.9 110.9 154.4 78.2 91.7 56.1 47.3 40.6 w40

(1) (2) (3) (4)

(1) (2) (3) (4)

(5) Extrapolate

(5) This volume

(B)xHC–B BZC2H5OH xZ1

2 3 4 5 N

32 32.0 26.5 36.9 18.7 21.9 13.4 11.3 9.7 w9.7

ICR ICR HP MS CERMS

1981BOM/BEA(b) 1982LAR/MCM 1994HIR/YAM 2003MAI/FED

((C2H5O)2H)C–C2H5OH

26.1G0.2

109G1

FT-ICR

2002FRI/MCM

(BH)C–C2H5OH BZ1,3-propanediol 1,4-butanediol

18.5G0.7 17.4G0.7

77.4G2.9 72.8G2.9

HP MS

1995CHE/STO

BHC–B BZOHCH2CH2OH

32.7G0.7

136.8G2.9

HP MS

1995CHE/STO

(CH3)2COHC–B, BZCH3C(O)OCH3

(1) 32.0

133.9

(1) ICR

(1) MCM/MCM

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

BHC–B

1293

(1) 29.7 (2) 29.1

124.3 121.8

(2) HP MS

(2) 1991SZU/MCM

(1,4-dioxane)HC– CH3C(O)OCH3

30.5

127.6

ICR

MCM/MCM

BHC–B, BZCH3C(O)OCHCH2

27.3

114.2

HP MS

1986KEE/CAS

CH3OHC–B, BZn-C3H7OH C2H5OHC–B BHC–B n-C4H9OHC–B (CH3)2OHC–B

30.3

126.8

ICR

1982LAR/MCM

32.1 31.6 31.5 30.4

134.3 132.2 131.8 127.2

(1) (2) (3) (2) (3) (4) (2) (3) (4) (2) (3) (4) (2) (3) (2) (3) (2) (2) (5)

131.4 127.2 100.0 90.4 74.9 79.1 60.2 54.4 59.4 49.8 46.0 49.0 45.6 39.7 46.4 36.8 45.6 46 w44

(1) ICR (2) Review (3) HP MS

(1) 1982LAR/MCM (2) 1992MEO (3) 1994HIR/YAM

(4) HP MS

(4) 1990HIR/MOR

(5) Extrapolate

(5) This volume

105.1G0.6

FT-ICR

2002FRI/MCM

(B)xHC–B, BZn-C3H7OH xZ1

2

3

4

5 6 7 8 N

((C3H7O)2H)C–C3H7OH

31.4 30.4 23.9 21.6 17.9 18.9 14.4 13.0 14.2 11.9 11.0 11.7 10.9 9.5 11.1 8.8 10.9 11 w10.6

25.1G0.1

(continued)

7366—CHAPTER 26—5/2/2007—12:15—JEBA—15382—XML MODEL B – pp. 1243–1349

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Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) (BH)C–i-C3H7OH BZC2H5OH (CH3)2O s-C4H9OH t-C4H9OH

(BH)C–i-C3H7OH, BZi-C3H7OH

(B)xHC–B, BZi-C3H7OH xZ1 2 3 4 5 6 7 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

33.6 31.0 32.0 30.5

140.6 129.7 133.9 127.6

ICR

1986KEE/CAS

31

129.7

ICR

1981BOM/BEA(b)

68.2 68.6 52.3 43.9 40.2 36.8 w33 w42

(1) HP MS

(1) 1994HIR/YAM

(2) Extrapolate

(2) This volume

IMS

1999EWI/EIC

(1) (1) (1) (1) (1) (1) (1) (2)

16.3 16.4 12.5 10.5 9.6 8.8 w7.9 w10.2

(c-C6H10CO)HC–B BZi-C3H7OH ((C3H7)2CO)HC–B

26.4

110.5

26.1

109.2

BHC–HCOOC2H5 BZHCOOC2H5 CH3)2O 1,4-dioxane

29.4 31.2 30.2

123.0 130.5 126.4

ICR

1982LAR/MCM

27.9G0.4

116.7G1.7

HP MS

1995CHE/STO

25.1G0.7

105.0G2.9

BHC–B, BZOHCH2CH2 CH2OH (OH(CH2CH2)2OH) HC–B

7366—CHAPTER 26—5/2/2007—12:16—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

BHC–B, BZ OH(CH2CH2)2OH

1295

30.2G0.9

126.4G3.8

HP MS

1995CHE/STO

(BH)C–CH3CO(C2H5) BZ(CH3)CO CH3CO(C2H5) (C2H5)2CO

33.5 30.4 30.4

140.2 127.2 127.2

ICR

1982LAR/MCM

BHC–B, BZ CH3COOC2H5

(1) 30.1 (2) 29.2

125.9 122.2

(1) ICR (2) HP MS

(1) 1982LAR/MCM (2) 1991SZU/MCM

BHC–B, BZ(C2H5)2O

(1) 31.2 (2) 29.8 (3) 31.2

130.5 124.7 130.5

(1) ICR (2) HP MS (3) HP MS

(1) 1982LAR/MCM (2) 1984MEO (3) 1991SZU/MCM

29.5 29.3 26.0

123.4 122.6 108.8

Review

1986KEE/CAS

32.3

135.1

ICR

1982LAR/MCM

28.9 28.5 27.0 24.5

120.9 119.2 113.0 102.5

IMS

1999EWI/EIC

24.1

100.8

IMS

1999EWI/EIC

(BH)C–(C2H5)2O BZ(C2H5)2CO (n-C3H7)2O (i-C3H7)2O

(Tetrahydrofuran) HC–(C2H5)2O

(BH)C–C2H5COCH3 BZC3H7OCOCH3 CH3COCH3 C4H9OH C4H9NH2

(DMMP)HC– C2H5COCH3 DMMPZdimethyl methylphosphanate

(continued)

7366—CHAPTER 26—5/2/2007—12:16—JEBA—15382—XML MODEL B – pp. 1243–1349

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Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

(DMDP)HC–B, BZnC4H9OH DMMPZdimethyl methylphos-phanate (2,4-lutidine)HC–B

21.6

90.4

20.8

87.0

(C2H5OH)HC–B, BZn-C4H9OH (C3H7OH)HC–B BHC–B

33.1

138.5

31.3 31.5

131.0 131.8

(i-C3H7OH)HC–B, BZs-C4H9OH BHC–B (c-C6H10CO)HC–B ((C3H7)2CO)HC–B (2,4-lutidine)HC–B

(1) (2) (1) (2) (2) (2)

33 28.1 32.6 27.8 27.6 21.3

(i-C3H7OH)HC–B, BZt-C4H9OH BHC–B ((C3H7)2CO)HC–B (c-C6H10CO)HC–B

(1) (2) (1) (2) (2)

31 28.9 31 26.7 27.0

(2,4-lutidine)HC– C4H9NH2

BHC–B, BZ MeCO(CH2)xCOMe xZ1 2

Methods (reference in parentheses)

References

IMS

1999EWI/EIC

Review

1986KEE/CAS

138.1 117.6 136.4 116.3 115.5 89.1

(1) ICR (2) IMS

(1) 1981BOM/BEA(b) (2) 1999EWI/EIC

129.7 120.9 129.7 111.7 113.0

(1) ICR (2) IMS

(1) 1981BOM/BEA(b) (2) 1999EWI/EIC

20.8

87.0

IMS

1999EWI/EIC

26.0 22.5

108.8 94.1

HP MS

1998MEO/SCH

7366—CHAPTER 26—5/2/2007—12:16—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1297

BHC–B, BZc-C3H5(CO)CH3

27.1

113.4

HP MS

1991SZU/MCM

BHC–B, BZ(C2H5)2CO

(1) (2) (3) (1) (1) (1) (1) (1)

126.4 120.9 130.5 133.5 1142.3 133.1 136.4 138.1

(1) ICR (2) HP MS (3) HP MS

(1) 1982LAR/MCM (2) 1991SZU/MCM (3) 1994MEO/SIE

BHC–B, BZMe(OCH2CH2)xOMe xZ1 (1) 22.8 (2) 27.4 2 (3) 21.3

95.4 114.6 89.1

HP MS

(1) 1984SHA/BLA (2) 1994MEO/SIE (3) 1994MEO/SIE

BHCBx–B, BZnC5H11OH xZ1 2 3 4 N

92.0 58.6 49.8 46.0 w44

(1) HP MS

(1) 1992MEO

(2) Extrapolate

(2) This volume

IMS

1999EWI/EIC

(CH3)(C2H5)COHC–B (CH3)2COHC–B BHC–B c-C4H8OHC–B (Tetrahydrofuran)HC–B

(1) (1) (1) (1) (2)

30.2 28.9 31.2 31.9 34.0 31.8 32.6 33.0

22.0 14.0 11.9 11.0 w10.5

(i-C3H7OH)HC–B, BZnC5H11OH (t-C4H9OH)HC–B (s-C4H9OH)HC–B

29.3

122.6

29.5 27.8

123.4 116.3

BHC–B, BZt-C5H11OH

31

129.7

ICR

1981BOM/BEA(b)

135.6 129.4 125.1 126.4 120.5 117.2 105.0

(1) ICR (2) HP MS (3) Derived

(1) 1982LAR/MCM (2) 1994MEO/SIE (3) 1984MEO

(4) IMS

(4) 1999EWI/EIC

(C2H5)2OHC–B, BZ(nC3H7)2O BHC–B (C2H5COCH3)HC–B (sC4H9OH)HC–B (nC4H9NH2)HC–B

(1) (2) (1) (3) (4) (4) (4)

32.4 30.9 29.9 30.2 28.8 28.0 25.1

(continued)

7366—CHAPTER 26—5/2/2007—12:16—JEBA—15382—XML MODEL B – pp. 1243–1349

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Comprehensive Handbook of Chemical Bond Energies

Table 26.1.2 (continued) BDEs in Positive Oxygen-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) (C2H5)2OHC–B, BZ(iC3H7)2O BHC–B

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 32.3 (1) 26.6 (2) 27.0

135.1 111.3 113.0

(1) ICR (2) HP MS

(1) 1982LAR/MCM (2) 1984MEO

29.4

123.0

IMS

1999EWI/EIC

28.1 26.9 25.1 22.6

117.6 112.5 105.0 94.6

BHC–B, BZCH3COO -t-C5H11

9.1

38.1

HP MS

1969FIE

(C6H10CO)HC–B, BZ (C3H7)2CO (C2H5COCH3)HC–B (CH3COCH3)HC–B

29.2

122.2

IMS

1999EWI/EIC

28.3 27.3

118.4 114.2

(C2H5COCH3)HC–B BZc-C6H10CO (CH3COCH3)HC–B

28.6 27.6

119.7 115.5

IMS

1999EWI/EIC

30.5

127.6

HP MS

1984MEO

22.0 20.8

92.0 87.0

IMS

1999EWI/EIC

(C3H7OC3H7)HC–B, BZ C4H9OC(O)CH3 (s-C4H9OH)HC–B (C4H9COOH)HC–B (C4H9NH2)HC–B (2,4-lutidine)HC–B

BHC–B, BZ(n-C4H9)2OH

(C2H5COCH3)HC–B BZ2,4-lutidine (C4H9NH2)HC–B

7366—CHAPTER 26—5/2/2007—12:16—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

(CH3)2OHC–B, BZ1,4dioxane (CH3)2COHC–B

(1) 31.7

132.6

(HCOOC2H5)HC–B

(1) (2) (1) (2) (2)

125.5 127.6 129.3 131.4 126.8

BHC–B, BZc-C5H10O BHC–B

32.6 33.2

(C2H5)2OHC 2 –C6H6

BHC–B, BZC6H5COCH3

BHC–B

BC(B)x–B, BZfuran xZ0 1

BxHC–B, BZtetrahydrofuran xZ0 1

1299

(1) HP MS

(1) 1984MEO

(2) ICR

(2) 1982LAR/MCM

136.4 138.9

HP MS

1984MEO

21

87.9

HP MS

1985DEA/MEO

26.8

112.1

HP MS

1991MEO/SIE

(1) 22.5 (2) 17.2 (2) !7

94.1 72.0 !29

HP MS

(1) 1986KEE/CAS (2) 1987HIR/TAK

(1) (2) (3) (4)

137.7 136.4 125.1 31.8

HP MS

(1) (2) (3) (4)

30.0 30.5 30.9 31.4 30.3

32.9 32.6 29.9 7.6

1982LAR/MCM 1984MEO 1986HIR/TAK 1987HIR/TAK

BHC–(CH3)2CO, BZtetrahydrofuran

31.5

131.8

ICR

1982LAR/MCM

(CH3)2COHC–B, BZtetrahydrofuran (C2H5)2COHC–B

(1) (2) (1) (2) (1) (2)

142.3 139.7 129.3 125.9 131.0 127.2

(1) ICR (2) HP MS

(1) 1982LAR/MCM (2) 1984MEO

114.6

HP MS

1986HIR/TAK

(C2H5)2OHC–B

BHC–B, BZ2methyltetrahydrofuran

34.0 33.4 30.9 30.1 31.3 30.4

27.4

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Comprehensive Handbook of Chemical Bond Energies

26.1.3 Negative oxygen-ion clusters/complexes Table 26.1.3 BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom) OK–Ar

kcal/mol

kJ/mol

Methods (reference in parentheses) PES

References

(1) 2.2G2.0

9.2G8.4

(2) 2.4

9.9

(1) 1995ARN/HEN

OK 2 –Ar

1.6

6.7

Photodetach.

1988BOW/EAT

OK–Kr

3.5

14.6

PES

2003CLE/HEN

OK–Xe

5.6

23.5

PES

2003CLE/HEN

OK–Cs

42.4G3.5

177.5G14.5

PES

1994SAR/HEN(b)

OK–Sc –Y

161.1G1.1 167.1G0.9

674.0G4.6 699.1G3.8

PES

1998WU/WAN

OK–Ti

155.9G2.0

652.3G8.4

Derived from EA

1996NIST

–V

146.9G1.0

614.6G4.2

(2) 2002CLE/HEN

in ref.

OK(O)x–Cr xZ0 1

OK–Mn

(1) 98.8G2.1

413.4G8.8

(2) 147.6G8.6

617.6G36

84.5G6.0

354G25

PES

(1) 1996WEN/GUN (2) 1997WEM/JON

Derived from EA

1996NIST

in ref.

OK–Fe

94.4G4.0

395.0G17

PES

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1997DRE/BOE

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

OK–Co

91.6G3.6

383G15

1301

Derived from EA

1996NIST

in ref.

OK–Ni

87.7G7.2

367G30

–Pd

59.4G3.0

249G12.6

OK–Cu

74.4G2.4

311G10

Derived from EA

1996NIST

in ref.

Derived from EA

1996NIST

in ref.

OK–Zn

68.2G1.0

285.4G4.2

Derived from EA

1996NIST

in ref.

OK–B

OK–Al

OK–H

(1) 216.5

906

(1) PES

(1) 1997WEN/KIM

(2) 206

861

(2) Derived

(2) 2003DEA/LI

(1) 149G12

623G50

(1) PES

(1) 1996DES/WU

(2) 195

815

(2) Derived

(2) 2003DEA/LI

(1) 110.7G0.2

463.1G0.8

(1) Derived

(1) 1974GUR/KAR

(2) 111

464.4

(2) Re-anal.

(2) 1990GOL/BIE

(3) 111.21G

465.28G0.34

(3) Derived from

(3) 1996NIST

DfH0 in ref.

0.08 –D

OK 2 –H

C(O)OK–H

(3) 112.1

469.0

(1) 66 (2) 63.8

276 266.9

(1) Derived (2) Re-anal.

(1) 1990NAS/VOL (2) 1990GOL/BIE

(3) 63.4G0.5

265.3G2.1

(3) CID

(3) 2003BLA/KAT

76

318

Derived from DfH0

1988LIA/BAR

in ref.

OK–Br

76.1

318.3

Derived

2000XIE/SCH

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1302

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom) OK–O

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 95.3

398.7

(1) Derived

(1) 1979HUB/HER

(2) 95.9G1 (3) 95.6G0.2

401.2G4.2 399.9G0.7

(2) PES (3) RecommendED

(2) 1989TRA/COW (3) 2003ERV/ANU

HOK–O

47.9G0.5

200.4G2.1

Derived

2003BLA/KAT

ClOK 3 –O

66G10

276G42

Derived from DfH0

1996NIST

in ref.

OK 2 –O

64.0

267.8

Derived

1986NIM/ELL

CH3OK–O

49.1G1.6

205.4G6.7

Derived

2003BLA/KAT

OK–S

(1) 116.1G2.1

485.8G8.8

(1) PES

(1) 1970FEL

(2) 101.6

425.1

(2) PES

(2) 1991POL/FIA

(3) 116.03G

485.47G0.10

(3) Derived from

(3) 1996NIST

0.02

EA in ref.

OK–Se

111.9G5.0

468.2G20.9

PES

1986COE/SNO

OK–Te

95.6G5.0

400G21

PES

1986FRE/COE

OK–N

(1) 121G2

506G8

(1) Derived

(1) 1974GUR/KAR

(2) 116.6

487.8

(2) Derived

(2) 1979HUB/HER

(3) 117.62G

492.11G0.50

(3) Derived from

(3) 1996NIST

0.37

OK–P

EA in ref.

(1) 133.5G0.8

558.6G3.3

(1) PES

(1) 1976ZIT/LIN

(2) 132.3G1.0

553.4G4.2

(2) Derived from

(2) 1996NIST

EA in ref.

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1303

OK–As

110.2G1.8

461.0G7.7

PES

1998LIP/XU

OK–Bi

84.3G4.6

353G19

Derived from EA in ref.

1996NIST

OK–C

(1) 187.5

784.5

(1) Derived

(1) 1979HUB/HER

(2) 254.1G0.2

1063.4G1.0

(2) Derived from

(2) 1996NIST

EA in ref.

OK–Sn

106.3G2.3

444.7G9.6

Derived from EA

1996NIST

in ref. –Pb

OK–O2

OK 2 ðO2 Þx –O2 xZ0

72.3G0.4

302.7G1.6

(1) 42

176

(1) CID

(1) 1978LIF/WU

(2) 38

159

(2) PF

(2) 1978COS/MOS

(3) 40.1

167.8

(3) Derived

(3) 1986NIM/ELL

(4) 39.0

163.1

(4) PD

(4) 1996GAR/SHE

(1) 13.6

56.9

(1) HP MS

(1) 1968CON/NES

(2) 10.5G0.5

43.9G2.1

(2) HP MS

(2) 1988HIR

(3) 9.0G1.2

37.6G4.8

(3) Photodetach.

(3) 1995CON/SHE

(4) 9.0G0.5

37.6G1.9

(4) PD

(4) 1996SHE/HAN

1

(2) 2.51G0.2

10.5G0.8

2

(2) 2.40G0.2

10.0G0.8

3

(2) 1.75G0.3

7.3G1.3

4 5

(2) 1.54G0.2 (2) 1.47G0.3

6.4G0.8 6.2G1.3

6

(2) w1.4

w5.9

N

(5) w1.6

w6.8

(5) Extrapolate

(5) This volume

xZ0

(1) 2.08G0.2

8.7G0.8

(1) HP MS

(1) 1988HIR

1

(1) 2.04G0.2

8.5G0.8

2 3

(1) 2.01G0.3 (1) 1.56G0.3

8.4G1.3 6.5G1.3

4

(1) w1.53

w6.4

N

(2) w1.6

w6.8

(2) Extrapolate

(2) This volume

OK 3 ðO2 Þx –O2

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1304

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

HOK–H2

w7

w29

CID

1984PAU/HEN

OK–OH

56.4G0.5

236.0G2.1

CID

2003BLA/KAT

OK–ClO

79.9G1.4

334.3G5.9

PES

1992GIL/POL

OK–SO

123.9G1.2

518.4G5.0

PES

1986NIM/ELL

OK–PO

165.5G2.5

692.5G10.5

PES

1996XU/DEB

OK–S2

112.6

471.1

PES

1986NIM/ELL

OK–HF

43.8G2.3

183.3G9.6

PPC

2005DEY/CON

HOK–HF

44

184

Derived

1971YAM/KEB

70.1

293

PhOK–HCl

39.1

164

Derived

1971YAM/KEB

HOK–HBr

79.3

332

Derived

1971YAM/KEB

86.3

361

OK–N2

11.2G2.9

46.9G12.1

Derived

1978TIE/WU

OK 2 –N2

6.0G1.0

25.1G4.2

PES

1988POS/JOH

–HCl

–HI

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1305

OK 3 ðN2 Þx –N2 xZ0

(1) 2.72G0.2

11.4G0.8

1 2

(1) 2.62G0.2 (1) 2.54G0.2

11.0G0.8 10.6G0.8 9.5G0.8

3

(1) 2.26G0.2

4

(1) 2.06G0.2

8.6G0.8

5

(1) 1.97G0.2

8.2G0.8

(1) HP MS

(1) 1988HIR

6

(1) 1.82G0.2

7.6G0.8

7

(1) 1.70G0.3

7.1G1.3

8

(1) 1.51G0.4

6.3G1.7

N

(2) w1.3

w5.6

(2) Extrapolate

(2) This volume

xZ0

(1) 2.87G0.2

12.0G0.8

(1) HP MS

(1) 1988HIR

1

(1) 2.79G0.2

11.7G0.8

OK 4 ðN2 Þx –N2

2

(1) 2.45G0.2

10.3G0.8

3

(1) 2.16G0.2

9.0G0.8

4

(1) 1.93G0.2

8.1G0.8

5 6

(1) 1.81G0.2 (1) 1.70G0.2

7.6G0.8 7.1G0.8

7

(1) 1.60G0.3

6.7G1.3

8

(1) w1.5

w6.4

N

(2) w1.3

w5.6

(2) Extrapolate

(2) This volume

OK–NO

92.0G0.2

384.9G0.9

PES

1988ERV/HO

HP MS

2003HIR/KAT

HP MS

2003HIR/KAT

(1) HP MS

(1) 2003HIR/KAT

OK 2 ðCOÞx –CO xZ0

3.5

14.6

w3.4

w14

xZ1

2.8

11.7

2

2.7

11.3

3

2.5

10.5

4 5

2.5 2.5

10.5 10.5

1

OK 3 ðCOÞx –CO

OK 4 ðCOÞx –CO xZ0

(1) 3.4

14.2

1

(1) 3.4

14.2

2

(1) 3.4

14.2

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1306

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ recommended data;

The broken bonds

Methods

reference in parentheses)

(boldfaceZdissociated atom)

kcal/mol

(reference in

kJ/mol

parentheses)

References

3

(1) 3.4

14.2

4 5

(1) 3.0 (1) 3.0

12.6 12.6

6

(1) 2.5

10.5

7

(1) 2.4

10.0

8

(1) 2.3

9.6

9

(1) 2.2

9.2

10

(1) 1.7

7.1

N

(2) w1.8

w7.5

(2) Extrapolate

(2) This volume

xZ0 1

2.8 2.7

11.7 113

Equilibrium

2003HIR/KAT

2

2.4

10.0

3

2.3

9.6

COK 3 ðCOÞx –CO

OK(CO2)x–CO2 xZ0

1

OK(H2O)–CO2

OK 2 ðCO2 Þx –CO2 xZ0

(1) 51

213

(1) FA

(1) 1977DOT/DAV

(2) 43.8

183.3

(2) PD

(2) 1979SMI/LEE

(3) 52G1

217.6G4.2

(3) PD

(3) 1980HIL/VES

(4) 57.7

241.4

(4) CIS

(4) 1981WU/TIE

(5) O52.3

O218.8

(5) PD

(5) 1985HUN/HOF

(6) 7.1

29.7

(6) HP MS

(6) 1980KEE/LEE

36.4

152.3

PD

1991ROE/SNO

(1) 18.4

77.0

(1) MS

(1) 1966PAC/PHE

(2) 19.0

79.5

(2) HP MS

(2) 1991HIR/YAM

1

(2) 6.57

27.5

(3) 7.1

29.7

(3) HP MS

(3) 1981KEE/LEE

2

(2) 6.34

26.5

3

(2) 4.79

20.0

4

(2) 4.46

18.7

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1307

5

(2) 4.21

17.6

6

(2) 3.99

16.7

N

(4) w5.7

w24

(4) Extrapolate

(4) This volume

50.3G2.5

210.5G10.5

Combined

1992SQU(b)

xZ0

(1) 7.27

30.4

Review

(1)1994HIR/YAM

1

(1) 6.68

27.9

(OH)K–CO2

NOK 2 ðCO2 Þx –CO2

2

(1) 6.34

26.5

3 4

(1) 6.04 (1) 5.23

25.3 21.9 20.7

5

(1) 4.94

6

(1) 4.42

18.5

7

(1) 4.19

17.5

N

(2) w5.7

w24

(2) Extrapolate

(2) This volume

(1) 7.1G0.1 (2) 5.94G0.2

29.7G0.4 24.9G0.8

HP MS

(1) 1980KEE/LEE (2) 1991HIR/YAM

COK 3 ðCO2 Þx –CO2 xZ0 1

(2) 5.73G0.2

24.0G0.8

2

(2) 5.50G0.2

23.0G0.8

3

(2) 5.22G0.2

21.8G0.8

4

(2) 4.80G0.2

20.1G0.8

5

(2) 4.65G0.2

19.5G0.8

6

(2) 4.45G0.2

18.6G0.8

N

(3) w5.7

w24

(3) Extrapolate

(3) This volume

w14

w58.6

Est. by exp.

1980KEE/LEE

xZ0

22.2

92.9

HP MS

1988MEO/CYB

1

17.3

72.4

(1) HP MS

(1) 1988MEO/CYB

OK 2 ðH2 OÞ–CO2

HCOOK(HCN)x–HCN

CH3COOK(HCN)x–HCN xZ0

(1) 22.2

92.9

(1) 16.6

69.5

2

(1) 14.8

61.9

3

(1) 12.0

50.2

1

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1308

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

4

(1) 9.8

41.0

N

(2) w6

w25

(2) Extrapolate

(2) This volume

CH3OK–CCH

101.7

425.5

Derived

1998SCH/BLA

(OH)K–SO2

61.3G2.5

256.5G10.5

Combined

1992SQU(b)

xZ0

(1) O59

O247

(1) FA

1986KEE/CAS

1

(2) 13.3

55.6

(2) HP MS

COK 3 –SO2

O14.2

O59.4

Est. by exp.

OK(SO2)x–SO2

OK–ONO

1980KEE/LEE

(1) 41.5

173.6

(1) CID

(1) 1981WU/TIE

(2) 32.3G0.7

135G3

(2) PD

(2) 1996OSB/LEA

(1) 23.1G1.2 (2) 5.4G0.2

96.5G4.8 22.6G0.8

(1) Photodetach. (2) HP MS

(1) 2000LI/CON (2) 1994HIR/FUJ(b)

OK(N2O)x–N2O xZ0 1 2

(2) 5.4G0.2

22.6G0.8

3

(2) 5.2G0.2

21.8G0.8

4

(2) 5.2G0.2

21.8G0.2

5

(2) 5.1G0.2

21.3G0.8

6

(2) 5.1G0.2

21.3G0.8

N

(3) w4

w16

(3) Extrapolate

(3) This volume

xZ0

8.8G0.2

36.8G0.8

HP MS

1994HIR/FUJ(b)

1

8.7G0.2

36.4G0.8

2

6.4G0.2

26.8G0.8

3

5.7G0.2

23.8G0.8

OK 2 ðN2 OÞx –N2O

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

4

5.3G0.2

22.2G0.8

5

5.0G0.3

20.9G1.3

xZ1

(1) 5.6G0.2

23.4G0.8

2

(1) 5.1G0.2

21.3G0.8

1309

NOK(N2O)x–N2O

3

(1) 4.5G0.2

18.8G0.8

4

(1) 4.5G0.2

18.8G0.8

(1) HP MS

(1) 1994HIR/FUJ(b)

5

(1) 4.4G0.2

18.4G0.8

6

(1) 4.2G0.3

17.6G1.3

N

(2) w4

w16

(2) Extrapolate

(2) This volume

xZ0

8.5

35.7

PES

1998KIM/WEN

1

7.8

32.8

PPC spectra

(1) 2001DEY/CLE

HOK(N2O)x–N2O

2

6.9

28.9

3

O6.5

O27.0

4

O4.6

O19.2

xZ0

(1) 26.5G1.8

111.0G7.7

1

(2) 16.4G1.8

68.5G7.7

xZ0

(1) 24.2G1.8

101.3G7.7

1

(2) 16.4G1.8

68.5G7.7

OK(H2O)x–H2O (2) 2001CLE/LUO

OK(D2O)x–D2O PPC spectra

(1) 2001DEY/CLE (2) 2001CLE/LUO

HOK(H2O)x–H2O xZ0

1

2

(1) 25.0

104.6

(1) HP MS

(1) 1971PAY/YAM

(2) 25.4

106.1

(2) MS

(2) 1972MEL

(3) 26.5G1

110.9G4

(3) HP MS

(3) 1986MEO/SPE

(4) 27.6

115.5

(4) HP MS

(4) 1990PAL/KEB

(5) 26.8

112.1

(5) HP MS

(5) 1999MEO/ELM

(1) 17.9

74.9

(3) 17.6G1 (5) 17.6

73.6G4 73.6 (6) Photodetach.

(6) 2001CLE/LUO

(7) MS

(7) 2003WAN/TSA

(6) 16.1G1.4

67.5G5.8

(1) w15.1

w63.2

(3) 16.2G1

67.8G4

(5) 16.2

67.8

(7) 16.2G0.5

67.8G2.1

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1310

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom) 3

4

recommended data; reference in parentheses) kcal/mol

kJ/mol

(3) 12.0G1

50.2G4

(5) 12.2 (7) 12.0G0.6

51.0 50.2G2.5

(3) 11.5G1

48.1G4

Methods (reference in parentheses)

(7) 10.9G0.7

45.6G2.9

5

(3) 11.2G1

46.9G4

(7) 11.5G0.5

48.1G2.1

6

(3) 10.4G1

43.5G4

7

(3) w9.8

w41

N

(8) w10.5

w44

(8) Extrapolate

References

(8) This volume

DOK(D2O)x–D2O xZ0

(1) 22.5

94.1

(1) HP MS

(1) 1970ARS/KEB

(2) 34.6

144.7

(2) MS

(2) 1970PAZ/GIA

(3) 26.8

112.1

(3) HP MS

(3) 1986MEO/SIE(b)

(1) 16.4

68.6

(2) 23.1

96.5 79.1G5.8 63.2

(4) Photodetach.

(4) 2001CLE/LUO

2

(4) 18.9G1.4 (1) 15.1 (2) w18.4

w77.2

3

(1) 14.2

59.4

4

(1) 14.1

59.0

1

OK 2 ðH2 OÞx –H2O xZ0

(1) 18.4

77.0

(1) HP MS

(1) 1970ARS/KEB

82.0G4.8 72.0

(2) Photodetach.

(2) 2001LUO/CLE

1

(2) 19.6G1.2 (1) 17.2 (2) 16.1G1.2

67.5G4.8

2

(1) 15.4

64.4

17.3G2.1

72.4G8.7

Photodetach.

1999LUO/CLE

xZ0 1

14.1G0.2 13.6G0.5

59.0G0.8 56.9G2.1

HP MS

1979KEE/LEE

2

13.1G0.8

54.8G3.3

OK 3 –D2O

COK 3 ðH2 OÞx –H2O

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1311

COK 4 ðH2 OÞx –H2O xZ0

w14.6

w61

1

w10.6

w44

Review

1986KEE/CAS

HP MS

1979KEE/LEE

(1) 1978MAC/BOH

HCOK 3 ðH2 OÞx –H2O xZ0

15.7G0.2

65.7G0.8

1

14.9G0.2

62.3G0.8

2

13.6G0.3

56.9G1.3

3

13.4G0.9

56.1G3.8

(CH3O)K(H2O)x–H2O xZ0

(1) 19.9

83.3

(1) FA

(2) 23.9

100.0

(2) HP MS

(2) 1986MEO

(3) 25.3G2.2

106G9

(3) CID

(3) 1999DET/ERV

80.3

1

(2) 19.2

2

(2) 14.8

61.9

3

(2) 11.0

46.0

N

(4) w10.5

w44

(4) Extrapolate

(4) This volume

HP MS

1986MEO

HP MS

1986MEO

ðCH3 OÞK 2 ðH2 OÞx –H2O xZ0

17.8

74.5

1

15.2

63.6

13.8

57.7

ðCH3 OÞK 3 –H2O

CH3CH2OK–H2O

(1) w22.3

w93

(1) Est. by exp.

(1) 1988CHA/BRA

(2) 24.4G2.2

102G9

(2) CID

(2) 1999DET/ERV

i-PrOK–H2O

21.2

88.7

Est. by exp.

1988CHA/BRA

t-BuOK–H2O

20.9

87.4

HCOOK(H2O)x–H2O xZ0

(1) 16.0

66.9

(1) HP MS

(1) 1986MEO/SIE(b)

1

(2) 13.8

57.7

(2) ES MS

(2) 1995BLA/KLA

2

(2) 12.1

50.6

15.4

64.4

HP MS

1988MEO

CH2CHOK–H2O

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1312

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(ClOOK)(H2O)x–H2O xZ0 1

16.0G1.5 13.4G1.5

66.9G6.3 56.1G6.3

2

11.8G1.5

49.4G6.3

ES MS

1995BLA/KLA

ES MS

1995BLA/KLA

ðClOK 3 ÞðH2 OÞx –H2O xZ0

13.2G1.5

55.2G6.3

1

11.7G1.5

49.0G6.3

11.8G1.5

49.4G6.3

ES MS

1995BLA/KLA

ES MS

1995BLA/KLA

ES MS

1995BLA/KLA

ES MS

1995BLA/KLA

ðClOK 4 Þ–H2O

ðBrOK 3 ÞðH2 OÞx –H2O xZ0

13.4G1.5

56.1G6.3

1

11.9G1.5

49.8G6.3

ðIOK 3 ÞðH2 OÞx –H2O xZ0

13.3G1.5

55.6G6.3

1 2

11.9G1.5 11.1G1.5

49.8G6.3 46.4G6.3

11.2G1.5

46.9G6.3

ðIOK 4 Þ–H2O

(CH3COO)K(H2O)x–H2O xZ0 1 2

(1) 16.4

68.6

(1) ES MS

(1) 1995BLA/KLA

(2) 15.9

66.5

(2) Review

(2) 1999MEO/ELM

(1) 13.8 (2) 12.9

57.7 54.0

(3) Extrapolate

(3) This volume

(1) 12.2

51.0

(2) 11.8

49.4

3

(2) w11

w46

N

(3) w10.5

w44

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1313

(B)K(BH)(H2O)x–H2O, BZCH3C(O)O xZ0 1

11.8 11.1

49.4 46.4

2

w11

w46

xZ0

9.1

38.1

1

8.1

33.8

Review

1999MEO/ELM

Review

1999MEO/ELM

(B)K(BH)2(H2O)x–H2O, BZCH3C(O)O

CF3COOK(H2O)x–H2O xZ0 1

(1) 13.7

57.3

(1) HP MS

(1) 1986MEO/SIE(b)

(2) 13.8

57.7

(2) ES MS

(2) 1995BLA/KLA

(2) 11.7

49.0

ES MS

1995BLA/KLA

ES MS

1995BLA/KLA

CHF2COOK(H2O)x–H2O xZ0

14.5

60.7

1

12.3

51.5

CH2FCOOK(H2O)x–H2O xZ0

15.3

64.0

1

12.9

54.0

2

11.6

48.5

14.7

61.5

ES MS

1995BLA/KLA

ES MS

1995BLA/KLA

ES MS

1995BLA/KLA

CH2ClCOOK–H2O

CHCl2COOK(H2O)x–H2O xZ0

13.8

57.7

1

11.9

49.8

CH2ICOOK–H2O xZ0

14.2

59.4

1

12.3

51.5

2

11.3

47.3

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1314

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom)

recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CH2CNCOOK (H2O)x–H2O xZ0 1

14.3 12.2

59.8 51.0

ES MS

1995BLA/KLA

C2H3COOK–H2O

16.0

66.9

HP MS

1986MEO/SIE(b)

ES MS

1995BLA/KLA

ES MS

1995BLA/KLA

ES MS

1995BLA/KLA

(1) HP MS

(1) 1988MEO

C2H4(OH) COOK(H2O)x–H2O xZ0

14.7

61.5

1

12.3

51.5

CH3CH2COOK (H2O)x–H2O xZ0

16.3

68.2

1

13.6

56.9

2

12.1

50.6

CH3OCH2COOK (H2O)x–H2O xZ0

15.6

65.3

1 2

13.1 11.8

54.8 49.4

xZ0

(1) 15.8

66.1

1

(1) 13.9

58.2

CH3 COCHK 2 ðH2 OÞx –H2O

2

(1) 13.0

54.4

3

(1) 10.8

45.2

N

(2) w10.5

w44

(2) Extrapolate

(2) This volume

CF3 COCHK 2 –H2O

12.8

53.6

HP MS

1988MEO

i-C3H7COOK–H2O

15.7

65.7

HP MS

1986MEO/SIE(b)

t-C4H9COOK–H2O

23.4

97.9

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1315

C9H19C(O) OK(H2O)x–H2O xZ0

13.0G0.3

54.4G1.3

1 2

10.4G0.3 9.5G0.3

43.5G1.3 39.7G1.3

Equilibrium

2005WYT/LIU

ES MS

2005LIU/SEU

[OT–H]C(H2O)x–H2O xZ0

7.4G0.3

31.0G1.3

1

8.3G0.3

34.7G1.3

2

7.4G0.3

31.0G1.3

OTZoxytocin

C6H5COOK(H2O)x–H2O xZ0

(1) 15.4

64.4

(1) HP MS

(1) 1986MEO/SIE(b)

(2) 15.1

63.2

(2) ES MS

(2) 1995BLA/KLA

1

(2) 12.7

53.1

2

(2) 11.5

48.1

N

(3) w10.5

w44

(3) Extrapolate

(3) This volume

PES

1998DIN/WAN

PES

1998DIN/WAN

Photodetach.

2003WAN/YAN

PES

2004YAN/FU

K

OOC(CH2)xCOOK–H2O xZ2

w8.1

w34

8.1

33.8

xZ3

12.7

53.1

4

13.4

56.0

5 6

13.4 14.1

56.0 58.9

3

K

OOC(CH2)x COOK(H2O)–H2O

(KO2C(O)C(O)OK)(H2O)x–H2O xZ3

11.8

49.2

4

7.8

32.8

5

7.4

30.9

4.4

18.3

14.3

59.8

ðKOCðCH2 Þ6 COK 2 ÞðH2 OÞx –H2O xZ0 1

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1316

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(Ala-Ala-H)K(H2O)x–H2O xZ0 1

11.7G0.2 9.6G0.2

48.9G0.8 40.2G0.8

Equilibrium

2004LIU/WYT

2

8.6G0.2

36.0G0.8

3

7.1G0.2

29.7G0.8

(Ala-Ala-H)K(Ala-Ala)–H2O

8.4G0.4

35.1G1.7

Equilibrium

2004LIU/WYT

(Gly-Gly-H)K(H2O)x–H2O xZ0

Equilibrium

2004LIU/WYT

AlaZalanine

11.0G0.3

46.0G1.3

1

9.5G0.3

39.7G1.3

2

8.2G0.3

34.3G1.3

3

7.4G0.1

31.0G0.4

7.5G0.3

31.4G1.3

Equilibrium

2004LIU/WYT

Equilibrium

2005WYT/LIU

GlyZglycine

(Gly-Gly-H)K(Gly-Gly)–H2O

(Asp)K(H2O)x–H2O xZ0

9.2G0.3

38.5G1.3

1

7.8G0.3

32.6G1.3

2

7.0G0.3

29.3G1.3

OK–PO2

149G16

623G67

PES

1999WAN/WAN

HOK–NH3

12

50

PES

2000SCH/DAV

HOK–HNO2

65

272

Derived

1971YAM/KEB

80.1

335

AspZHO(O)CCH2CH(NH2)– C(O)O

–HNO3

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1317

OK 2 –CH3

46.2G1.2

193.3G5.0

Derived

2003BLA/KAT

COOK–CH3

72.9G4.6

305G19.3

Photodetach.

2004LU/CON

HCOOK–CH3

22.7

95.0

Derived

1998SCH/BLA

(p-Benzoquinone)K–SiF4

24G2

100.4G8.4

HP MS

2001WIL/KNI

OK–CH3O

51.8G1.4

216.7G5.9

Derived

2003BLA/KAT

MeOK–HCF3 EtOK–HCF3

23.5 22.0

98.3 92.0

FT-ICR

1998CHA/BRA

i-PrOK–HCF3

21.1

88.3

HCOOK(HCOOH)x–HCOOH xZ0

(1) 36.8

154.0

(1) HP MS

(1) 1986MEO/SIE(b)

1

(2) 26.1G3.1

109.2G13.0

(2) HP MS

(2) 1978LUC/WLO

2

(2) 20.0G2.6

83.7G10.9

3 4

(2) 14.2G2.1 (2) 10.1G2.0

59.4G8.8 42.3G8.4

N

(3) w11

w46

(3) Extrapolate

(3) This volume

xZ0

19.1

79.9

HP MS

1973YAM/PAY

1

15.5

64.9

2

13.5

56.5

HCOOK–CH3OH

36.8

154.0

HP MS

1986MEO/SIE(b)

CH3COOK–CH3OH

17.6

73.6

HP MS

1988MEO(d)

HP MS

(1) 1986MEO

K OK 2 ðCH3 OHÞx –CH3OH

CH3OK(CH3OH)x–CH3OH xZ0 1

(1) 29.3

122.6

(2) 28.8

120.5

(1) 21.4

89.5

(2) 1986MEO/SIE(b)

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1318

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom)

recommended data; reference in parentheses) kcal/mol

kJ/mol

2

(1) 15.0

62.8

3

(1) 11.4

47.7

CH3OK–CH3OD

28.3G0.1

118.4G0.4

CH3OK–CD3OD

28.1G0.1

117.6G0.4

CD3OK–CD3OD

28.5G0.1

119.2G0.4

CH3OK–CD3OH

CD3OK–CD3OH

C2H5OK–CH3OH

Methods (reference in parentheses)

References

Ion flow tube

1990BAR/DAN

(1) 28.5G0.1

119.2G0.4

(1) Ion flow tube

(1) 1990BAR/DAN

(2) 28.3

118.4

(2) FT-ICR

(2) 2000CHA/BRA

(1) 28.9G0.1

120.9G0.4

(1) Ion flow tube

(1) 1990BAR/DAN

(2) 28.2

118.0

(2) FT-ICR

(2) 2000CHA/BRA

(1) 20.2

84.5

(1) ICR

(1) 1984CAL/ROZ

(2) 25.6G2

107G8

(2) CID

(2) 1999DET/ERV

nC3H7OK–CH3OH

19.8

82.8

ICR

1984CAL/ROZ

iC3H7OK–CH3OH

21.0G2.2

88G9

CID

1999DET/ERV

(1) 1984CAL/ROZ

t-C4H9OK–CH3OH

(1) 18.9

79.1

(1) ICR

(2) 25.5

106.7

(2) HP MS

(2) 1986MEO/SIE(b)

(3) 23.4G2.2

98G9

(3) CID

(3) 1999DET/ERV

t-C5H11OK–CH3OH

18.6

77.8

ICR

1984CAL/ROZ

CH3COOK–CH3SH

14.9

62.3

HP MS

1988MEO(d)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1319

K OK 2 ðCH3 CNÞ –CH3CN

xZ0

16.4

68.6

1 2

14.2 11.9

59.4 49.8

HP MS

1973YAM/PAY

3

9.5

39.7

CH3 COCHK 2 –CH3CN

15.3

64.0

HP MS

1988MEO

CH3COOK–CH3CN CH3COOK–CH3C(O)H

14.8

61.9

HP MS

1988MEO(d)

16.3

68.2

xZ0

29.3

122.6

HP MS

1986MEO/SIE(b)

1

19.6

82.0

2

16.2

67.8

xZ1 2

15.6 11.9

65.3 49.8

Review

1999MEO/ELM

OK–CH3CCH

70.5

295

Derived

1998SCH/BLA

OK–CH2CCH2

71.5

299

C6H5OK–CH3COOH

27.4

114.6

HP MS

1986MEO/SIE(b)

CH3COOK–CH3COOH

29.3

122.6

HP MS

1986MEO/SIE(b)

(B)K(BH)x–B, BZCH3COOH

(B)K(BH)x(H2O)–B BZCH3CO2H

C2H5OK–C2H5OH

(1) 20.6

86.2

(1) ICR

(1) 1984CAL/RAZ

(2) 27.6

115.5

(2) HP MS

(2) 1986MEO/SIE(b)

n-C3H7OK–B, BZC2H5OH

20.3

84.9

ICR

1984CAL/RAZ

t-C4H9OK–B

19.5

81.6

t-C5H11OK–B

19.2

80.3

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1320

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ The broken bonds (boldfaceZdissociated atom) HCOOK–C2H5OH

recommended data; reference in parentheses) kcal/mol 20.7

kJ/mol

Methods (reference in parentheses)

References

86.6

HP MS

1988MEO(d)

HP MS

1986MEO/SIE(b)

HCOOK–B, BZC2H5OH

20.7

86.6

C6H5OK–B

19.3

80.8

i-C3H7COOK–i-C3H7COOH

29.9

125.1

HP MS

1986MEO/SIE(b)

H2CC(CH3)OK–n-C3H7OH

14.5

60.7

ICR

1984CAL/RAZ

n-C3H7OK–B, BZC3H7OH t-C4H9OK–B

21.0 20.2

87.9 84.5

ICR

1984CAL/RAZ

t-C5H11OK–B

19.8

82.8

xZ0

15.7

65.7

HP MS

1988MEO(d)

1

10.8

45.2

ICR

1984CAL/RAZ

ICR

1984CAL/RAZ

HP MS

1988MEO(d)

CH3COOK(B)x–B, BZ CH3C(O)CH3

t-C4H9OK–B, BZt-C4H9OH

20.4

85.4

t-C5H11OK–B

20.3

84.9

t-C5H11OK–B, BZtC5H11OH

21.5

90.0

t-C4H9CH(CH3)OK–B

21.3

89.1

25.4

106.3

16.4

68.6

CH3COOK(B)x–B BZCH3C(O)NHCH3 xZ0 1

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1321

CH3COOK(B)x–B BZCH3C(O)-Ala-OCH3 xZ0 1

31.4 21.2

131.4 88.7

HP MS

1988MEO(d)

xZ0

24.0

100.4

HP MS

1988MEO(d)

1

17.9

74.9

tC4H9CH(CH3)OK–B, BZtC4H9CH(CH3)OH

21.4

89.5

ICR

1984CAL/RAZ

C6H5CH2OK–B

21.6

90.4

CH3COOK–(CH3OCH2CH2)2O

15.1

63.2

HP MS

1986MEO/SIE(b)

SiF2OK–C6H5

117.6G1.6

492.0G6.7

FA MS

2003KRO/LAR

OK 2 –C6H6

14.1

58.9

PES

2002BAR/SCH

CH3COOK–B, BZC6H5OH

(1) 26.1

109.2

HP MS

(1) 1988MEO(d)

C6H5COOK–B

(2) 26.1

109.2

AlaZNHCH(CH3)C(O)

CH3COOK(B)x–B, BZpyrrole

C6H5CH2OK–C6H5CH2OH

OK 2 ðH2 OÞx –pyridine xZ0

(1) 22.3

93.3

(1) ICR

(1) 1984CAL/RAZ

(2) 23.8

99.6

(2) HP MS

(2) 1986KEE/CAS

PES

2002BAR/SCH

PES

2002BAR/SCH

21.7

90.7

32.7

137.0

xZ0

22.1

92.6

1

37.8

158.2

2

52.3

219.0

1

(2) 1986MEO/SIE(b)

OK 2 ðH2 OÞx –naphthalene

(continued)

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

1322

Comprehensive Handbook of Chemical Bond Energies

Table 26.1.3 (continued) BDEs in Negative Oxygen-Ion Clusters/Complexes BDEs (boldfaceZ recommended data;

The broken bonds

reference in parentheses)

(boldfaceZdissociated atom)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

CHOK–Fe(CO)4

90G5

377G21

Derived

1988LAn/SQU

CH3COK–B, BZFe(CO)4

83

347

Derived

1993SUN/SQU(b)

HC(O)OK–B

81

339

CH3C(O)OK–B

88

368

CHOK–Cr(CO)5

w73

w305

Review

2004DAM

–Mo(CO)5

w77

w322

–W(CO)5

w82

w343

HOK–B, BZFe(CO)5

53–60

222–251

Ion reactions

1985LAN/SAL

MeOK–B

39–51

163–214

EtOK–B

%45.7

%191

nPrOK–B

%44.3

%185

nBuOK–B

%43.6

%182

(1) ES MS

(1) 2003BLA/PES

(2) Extrapolate

(2) This volume

tBuOK–B

%42.9

%180

MeC(O)OK–B

%29.5

%123

CF3CH2OK–B MeOCH2CH2OK–B

R34.0 %42.1

R142 %176

(croconate)2K(H2O)x–H2O xZ3

(1) 17.2

72.0

4

(1) 14.0

58.6

5

(1) 12.1

50.6

6

(1) 12.6

52.7

7 N

(1) 10.6 (2) w10.5

44.4 w44

7366—CHAPTER 26—5/2/2007—12:17—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1323

26.2 Sulfur and the ion clusters/complexes 26.2.1 Sulfur clusters/complexes Table 26.2.1 BDEs in Sulfur Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

SO–He

w0.1, at 0 K

w0.3

Mol. beam

1997AQU/ASC

SO–Ne

w0.1, at 0 K

w0.5

Mol. beam

1997AQU/ASC

HS–Ne

(1) 0.1, at 0 K (2) 0.30

w0.4 1.24

Spectroscopy

(1) 1997YAN/CAR (2) 1999CAR/MIL(b)

HS–Ar

(1) 1.31, at 0 K (2) 1.64

5.48 6.84

Spectroscopy

(1) 1997YAN/CAR (2) 1999CAR/MIL

SO–Ar

w0.4, at 0 K

w1.6

Mol. beam

1997AQU/ASC

Tetrahydrothiophene-Ar

0.5, at 0 K

2.1

Spectroscopy

1999SAN/LOP

HS–Kr

(1) 3.64, at 0 K (2) 3.69

15.23 15.46

Spectroscopy

(1) 1997YAN/CAR (2) 1999CAR/MIL

SO–Kr

w0.5, at 0 K

w2

Mol. beam

1997AQU/ASC

SO–Xe

w0.5, at 0 K

w2.2

Mol. beam

1997AQU/ASC

(CH3)2S–Cl

w16, at 0 K

w67

Spectroscopy

2004ENA/NAK

(CH3)2S–Br

12G1, at 0 K

50.2G4.2

Spectroscopy

2001NAK/GOT (continued)

7366—CHAPTER 26—5/2/2007—12:18—JEBA—15382—XML MODEL B – pp. 1243–1349

1324

Comprehensive Handbook of Chemical Bond Energies

Table 26.2.1 (continued) BDEs in Sulfur Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(CH2)2S–HF

5.56, at 0 K

23.28

FT-IR

2004ASS/GOU

SO2–HCl

3.5, at 0 K

14.6

IR spectra

1959BUR/SMI

SO3–H2O

13

54.4

Flow reactor

1996LOV/HAN

H2SO4–H2O

10.6

44.3

Est. by exp.

2000NOP

H2S–H2S

3.6, at 0 K

15.1

Spectroscopy

1990SEN/RAL

HSH–NH3

2.84, at 0 K

11.88

Spectroscopy

1995HIL/FRA

SO3–NH3

24G1

100.4G4.2

Flow reactor

1997LOV

Me2S–GaCl3 –GaBr3 –GaI3

54.2 50.6 40.2

227 212 168

Thermochem.

1966GRE/SRI

Et2S–GaCl3 –GaBr3 –GaI3

56.2 51.8 40.8

235 217 171

Thermochem.

1966GRE/SRI

SO2–transK2-C4H8 SO2–C6H6

3.85G0.23, at 0 K 16.1G1.0 4.40G0.28 18.4G1.2

PI

1985GRO/WAL

SF6–C6H5CH3

3.57G0.06, at 0 K 14.95G 0.24

ZEKE

1999GEP/DES

7366—CHAPTER 26—5/2/2007—12:18—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1325

26.2.2 Positive sulfur-ion clusters/complexes Table 26.2.2 BDEs in Positive Sulfur-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

O2SC–Kr

7

29

PD

1986KIM/JAR

SC–H

(1) 86G4 (2) 82.5 (3) 83.2G0.4

360G17 345.3 348.2G1.7

(1) Derived (2) Derived (3) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1984ROS/HOR (3) 1996NIST

CH2SHC–H

48.2

201.6

Derived

1997CHE/FEN

CH3CHSHC–H

33.9

141.8

Derived

1997CHE/FEN

SC(F)x–F xZ0 1 2 3 4 5

82.1G1.2 96.2G2.3 104.7G1.8 77.5G1.2 106.1G2.3 88.1G3.2

343.5G4.8 402.3G9.6 438.0G7.7 324.2G4.8 443.8G9.6 368.6G 13.5

CID

1992FIS/KIC

SC(Cl)x–Cl xZ0 1

90.9 59.7

380 245

MS

1981KAU/VAH

SC–O

(1) 85G10 (2) 125.3G0.1

356G42 524.3G0.4

(1) Derived (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

SC–S

(1) 123.8 (2) 124.9G0.1

518.1 522.4G0.5

(1) Derived (2) PI

(1) 1979HUB/HER (2) 1986LIA/NG(b) (continued)

7366—CHAPTER 26—5/2/2007—12:18—JEBA—15382—XML MODEL B – pp. 1243–1349

1326

Comprehensive Handbook of Chemical Bond Energies

Table 26.2.2 (continued) BDEs in Positive Sulfur-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) HC(S)x–S xZ1 2 3 4 5

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

15.4G0.5 9.1G0.5 8.4G0.5 6.7G0.3 w6.1

64.4G2.1 38.1G2.1 35.1G2.1 28.0G1.3 w25.5

HP MS

1977HIR/KEB

(1) 120G10 (2) 123G8

502G42 516G34

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

(2) 137G5

573G21

SC–C

(1) 147.1 (2) 148.4G0.3

615.6 620.8G1.3

(1) Derived (2) MS

(1) 1979HUB/HER (2) 1995COP/DRO

SC–CS2

39.7

166

PI

1981ONO/LIN

91.6 120.5 129.3 34.7 23.0 w26.7

(1) HP MS (2) PI (3) HP MS

(1) 1977MEO/FIE (2) 1981ONO/LIN (3) 1994HIR/FUJ

1 2 N

(1) (2) (3) (3) (3) (4)

(4) Extrapolate

(4) This volume

CSC–CS2

36.0

150.6

PI

1981ONO/LIN

(1) (2) (3) (2) (3) (2)

91.6 73.2 104.2 18.4 27.2 16.3

(1) HP MS (2) PI (3) HP MS

(1) 1977MEO/FIE (2) 1980ONO/LIN (3) 1994HIR/FUJ

SC–N

–P

SC 2 ðCS2 Þx –CS2 xZ0

CSC 2 ðCS2 Þx –CS2 xZ0

1 2

21.9 28.8 30.9 8.3 5.5 w6.4

21.9 17.5 24.9 4.4 6.5 3.9

7366—CHAPTER 26—5/2/2007—12:18—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

3 N

HCSC 2 ðCS2 Þ–CS2 xZ0

(3) (2) (3) (4)

4.9 2.6 2.6 w6.4

20.5 10.9 10.9 w26.7

1327

(4) Extrapolate

(4) This volume

(1) 11.1 (2) 9.0 (2) 4.7

46.4 37.7 19.7

HP MS

(1) 1977MEO/FIE (2) 1993HIR/FUJ

OSC–SO2 O2SC–SO2

13.8 15.2

57.7 63.6

PI

1981ERI/NG

O2SHC–SO2

23.2

97.1

HP MS

1986MCM/KEB

(1) (2) (1) (2) (3)

17.2 23.9G2.0 1.6 7.8G0.4 6.3

72.0 100.0G8.4 6.7 32.6G1.7 26.4

HP MS

(1) 1981ONO/OSU (2) 2004HII/NAK

HOCSC(OCS)x–OCS xZ0 1 2 N

(1) (1) (1) (2)

13.5G1.0 5.7G0.3 4.3G0.5 w4.4

56.5G4.2 23.8G1.3 18.0G2.1 w18.5

(1) HP MS

(1) 2005HIR/FUJ(b)

(2) Extrapolate

(2) This volume

OCSC(OCS)x–CO2 xZ0 1

17.2 1.6

72.0 6.7

PI

1981ONO/OSU

SOC 2 –CO2

10.2

42.7

HP MS

1988ILL

H3SC(H2S)x–H2O xZ0

(1) 17.0

71.1

HP MS

(1) 1977MEO/FIE

1

OCSC(OCS)x–OCS xZ0 1 2

(3) 2005HIR/FUJ(b)

(continued)

7366—CHAPTER 26—5/2/2007—12:18—JEBA—15382—XML MODEL B – pp. 1243–1349

1328

Comprehensive Handbook of Chemical Bond Energies

Table 26.2.2 (continued) BDEs in Positive Sulfur-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 1 2 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (2) (2) (2) (3)

21.9 19.8 10.7 w10.5

Methods (reference in parentheses)

kJ/mol

References

91.6 82.8 44.8 w44

(2) 1977HIR/KEB

(3) Extrapolate

(3) This volume

CH3 SHC 2 –H2O

(1) 15.5 (2) 13.5

64.9 56.5

(1) HP MS (2) ICR

(1) 1985MEO/SIE (2) 1986KEE/CAS

C2 H5 SHC 2 –H2O

14.7

61.5

HP MS

1985MEO/SIE

(1) 13.1 (2) 12.0 (1) 11.6

54.8 50.2 48.5

(1) HP MS (2) ICR

(1) 1985MEO/SIE (2) 1986 KEE/CAS

(R1R2S)HC–H2O R1 R2 Me Et n-Pr n-Pr

12.6 12.2

52.7 51.0

HP MS

1985MEO/SIE

BHC(H2O)x–H2O BZtetrahydrothiophene xZ0 1

11.5 10.4

48.1 43.5

HP MS

1987HIR/TAK

BHC–H2O, BZthiophene 10.2

42.7

HP MS

1987HIR/TAK

BC–H2O, BZ Tetrahydrothiophene thiophene

9.5

39.7

HP MS

1987HIR/TAK

(1) 17.0G0.3

71.1G1.3

PI

(1) 1981WAL/BLA

(CH3)2S(H2O)xHC–H2O xZ0 1

H2SC(H2S)x–H2S xZ0

7366—CHAPTER 26—5/2/2007—12:18—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1 2 3 4 N

H3SC(H2S)x–H2S xZ0

1

2

3

4 N

1329

(2) (1) (2) (1) (1) (1) (3)

21.2G0.9 3.2G0.3 4.2G0.9 1.2G0.3 1.4G0.3 2.6G0.3 w3.4

88.7G3.9 13.4G1.3 17.6G3.9 5.0G1.3 5.9G1.3 10.9G1.3 w14.1

(2) 1983PRE/TZE

(1) (2) (3) (4) (1) (2) (4) (1) (2) (4) (1) (2) (4) (1) (5)

15.4 12.8G1.5 10.6G2.3 10.8 9.1 7.2 6.0 8.4 5.4 4.4 6.7 3.3 2.5 w6.1 w3.4

64.4 53.6G6.3 44.4G9.6 45.2 38.1 30.1 25.1 35.1 22.6 18.4 28.0 13.8 10.5 w25 w14

(5) Extrapolate

(5) This volume

(3) Extrapolate

(3) This volume

(1) (2) (3) (4)

(1) (2) (3) (4)

HP MS HP MS PI PI

1977HIR/KEB 1977MEO/FIE 1983PRE/TZE 1984WAL/BLA

F5SC–H2S

50.7G11.5

212G48

SIFDT

1993ZAN/HAN

CH2SHC–CH3

39.9

167

Derived

1997CHE/FEN

H3SC–CH4

3.9

16.3

HP MS

1972BEN/FIE(c)

OCSC–C2H2

(1) 33.7 (2) 20.2

141 84.4

(1) PD (2) MS

(1) 1990ORL/FRI (2) 1991GRA/BOW

9.4 3.4 3.0

39.3 14.2 12.6

HP MS

1995HIR/SHI(b)

SCðSF6 ÞC x –SF6 xZ0 1 2

(continued)

7366—CHAPTER 26—5/2/2007—12:18—JEBA—15382—XML MODEL B – pp. 1243–1349

1330

Comprehensive Handbook of Chemical Bond Energies

Table 26.2.2 (continued) BDEs in Positive Sulfur-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

SF(SF6)x–SF6 xZ0 1 2

9.1 3.8 3.7

38.1 15.9 15.5

HP MS

1995HIR/SHI(b)

SFC 2 ðSF6 Þx –SF6 xZ0 1 2

7.8 5.0 4.2

32.6 20.9 17.6

HP MS

1995HIR/SHI(b)

SFC 3 ðSF6 Þx –SF6 xZ0 1 2

7.4 4.5 4.0

31.0 18.8 16.7

HP MS

1995HIR/SHI(b)

SFC 4 ðSF6 Þx –SF6 xZ0 1

7.2 4.6

30.1 19.2

HP MS

1995HIR/SHI(b)

SFC 5 ðSF6 Þx –SF6 xZ0 1

4.7 3.6

19.7 15.1

HP MS

1995HIR/SHI(b)

(CH3)2SOHC((CH3)2O)x– (CH3)2O xZ0 30.8 1 21.3

129 89.1

HP MS

1980LAU/SAL

(CH3)2SOHC–(CH3)2CO (CH3)2CSHC–(CH3)2SO

101 129

HP MS

1980LAU/SAL

24.1 30.8

7366—CHAPTER 26—5/2/2007—12:18—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1331

(C2H6S)C–SC2H6

26.8

112

Equilibrium

1995DEB/ILL

(CH3)2CSHC–(CH3)2CS CH3(C2H5)CSHC– CH3(C2H5)CS

26.4 26.6

110 111

HP MS

1985MEO/SIE

(c-C4H8S)C–B, BZcSC4H8 (c-SC5H10S)C–B

27.5G0.2

115G1

Equilibrium

1998ILL

25.8G0.5

108G2

(c-C5H10S)C–c-SC5H10

25.3G0.5

106G2

Equilibrium

1998ILL

c-C4H4SC–C6H6

13

54

HP MS

1969FIE/HAM

C SC 4 –S4 C C S5 –S3

49.5 32.5

207 136

Derived

2004KRO/PAS

(R2SS–SSR20 )C RZMe, R 0 ZMe Me, Et Et, Et n-Pr, n-Pr

27.5, at 0 K 25.6 28.7 w29.4

115 107 120 w123

Equilibrium

1996JAM/ILL

26.2.3 Negative sulfur-ion clusters/complexes Table 26.2.3 BDEs in Negative Sulfur-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) SK(Al)x–Al xZ0 1

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol 101.6G1.7 40.2G5.2

kJ/mol 425.1G7.1 168G22

Methods (reference in parentheses) PES

References 1995NAK/TAG (continued)

7366—CHAPTER 26—5/2/2007—12:18—JEBA—15382—XML MODEL B – pp. 1243–1349

1332

Comprehensive Handbook of Chemical Bond Energies

Table 26.2.3 (continued) BDEs in Negative Sulfur-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

SK(AlS)–Al

42.3G7.6

177G32

PES

1995NAK/TAG

SK–H

89.2G1.0

373.1G4.3

CID

2000REM/ERV

F5SK–H

31.1G2.3

130.3G9.6

MS

1988CHE/SHU

SK–O

(1) 100G10 (2) 101.8G0.1

418G42 426.0G0.5

(1) Derived (2) Derived from EA in ref.

(1) 1974GUR/KAR (2) 1996NIST

SK 2 –O

107.7

451

Derived

1986NIM/ELL

SOK–O

131.7

551

Derived

1986NIM/ELL

SK–S

(1) 130G10 (2) 92.3G0.3

544G42 386.0G1.4

(1) Derived (2) Derived from EA in ref.

(1) 1974GUR/KAR (2) 1996NIST

SK 2 –S SOK–S

75.3 98.3

315 411

Derived

1986NIM/ELL

SK–Se

102

427

Derived

1974GUR/KAR

SK–N

(1) 92G10 (2) 90.3G5.7

385G42 378G24

Derived

(1) 1974GUR/KAR (2) 2003DEA/LI

SK–C

127.3G0.6

532.7G2.4

Derived from EA in ref.

1996NIST

7366—CHAPTER 26—5/2/2007—12:18—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1333

SK–SO SK–S2

76.4 66.1

320 277

Derived

1986NIM/ELL

HSOK 4 –HCl

15.7G1

65.7G4

FA

1984BOH/FAH

HSK–HCN

(1) 21 (2) 17.4G9.3

87.9 73G39

(1) HP MS (2) CID

(1) 1998MEO(d) (2) 2006AKI/ERV

(1) (1) (2) (3)

91.6 27.2 17.2G2.5 18.4G4.6

(1) HP MS

(1) 1994HIR/FUJ

(2) Photodetach. (3) PES

(2) 1988BOW/EAT (3) 1997TSU/HIR

CSK 2 ðCS2 Þx –CS2 xZ0 1

21.9 6.5 4.1G0.6 4.4G1.1

SOK 2 ðSO2 Þx –H2O xZ1 2 3 4 5

8.9G0.8 7.4G0.2 7.6G0.3 7.5G0.4 6.5G0.2

37.2G3.3 31.0G0.8 31.8G1.3 31.4G1.7 27.2G0.8

Equilibrium

1994VAC/DUC

SOK 2 ðH2 OÞðSO2 Þx –H2O xZ3 4

7.1G0.4 7.1G0.7

29.7G1.7 29.7G2.9

Equilibrium

1994VAC/DUC

SOK 2 ðH2 OÞ2 ðSO2 Þx –H2O xZ3 4

6.6G0.3 7.1G0.7

27.6G1.4 29.7G2.9

Equilibrium

1994VAC/DUC

SOK 3 –H2O

w13

w54.4

Est. by exp.

1980KEE/LEE

SOK 4 –H2O

w12.5

w52.3

Est. by exp.

1980KEE/LEE

HSK(H2O)x–H2O xZ0

(1) 14.2G0.2

59.4G0.8

(1) HP MS

(1) 1989SIE/MEO (continued)

7366—CHAPTER 26—5/2/2007—12:19—JEBA—15382—XML MODEL B – pp. 1243–1349

1334

Comprehensive Handbook of Chemical Bond Energies

Table 26.2.3 (continued) BDEs in Negative Sulfur-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kJ/mol

Methods (reference in parentheses)

References

(1) 12.6G0.3 (1) 11.7G0.5 (2) w10.5

52.7G1.3 49.0G2.1 w44

(2) Extrapolate

(2) This volume

(OCS)K(H2O)x–H2O xZ0 1

47.7 10.6

199.7 44.4

PES

2002SUR/SAN

CH3SK(H2O)x–H2O xZ0 1 2 3 N

(1) (1) (1) (1) (2)

15.0G0.2 13.5G0.4 11.1G0.1 9.6G0.4 w10.5

62.8G0.8 56.5G1.7 46.4G0.4 40.2G1.7 w44

(1) HP MS

(1) 1989SIE/MEO

(2) Extrapolate

(2) This volume

(1) (2) (2) (2) (2) (2) (2) (2) (2) (3)

11.9 12.9 11.2 12.4 13.2 11.7 11.4 11.1 11.2 w10.5

49.8 54.0 46.9 51.9 55.2 49.0 47.7 46.4 46.9 w44

(1) FA (2) MS

(1) 1984BOH/FAH (2) 2003FRO/LOV

(3) Extrapolate

(3) This volume

36.4 39.7 46.4

MS

2003FRO/LOV

50.6 49.0

MS

(1) 1982ARN/VIG (2) 2003FRO/LOV

1 2 N

(HSO4)K(H2O)x–H2O xZ0 1 2 3 4 5 6 7 N

kcal/mol

(HSO4)K(H2SO4)(H2O)x– H2O xZ0 8.7 1 9.5 2 11.1

(HSO4)K(H2SO4)2 (H2O)x–H2O xZ0

(1) 12.1 (2) 11.7

7366—CHAPTER 26—5/2/2007—12:19—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1 2 3

(2) 13.6 (2) 10.9 (2) 11.3

1335

56.9 45.6 47.3

(HSO4)K(H2SO4)3(H2O)x–H2O xZ0 (1) 13.8 (2) 15.1 1 (1) 13.0 (2) 12.5 2 (2) 12.9 3 (2) 11.9 4 (2) 9.3 5 (2) 10.4 6 (2) 10.6 7 (2) 12.3 8 (2) 11.7 N (3) w10.5

57.7 63.2 54.4 52.3 54.0 49.8 38.9 43.5 44.4 51.5 49.0 w44

(HSO4)K(H2SO4)4(H2O)x–H2O xZ0 (1) 13.9 (2) 15.1 1 (2) 14.0 2 (2) 14.1 3 (2) 13.8 4 (2) 12.2 5 (2) 12.8 6 (2) 13.3 7 (2) 13.1 8 (2) 13.5 9 (2) 12.7 N (3) w10.5

58.2 63.2 58.6 59.0 57.7 51.0 53.6 55.6 54.8 56.5 53.1 w44

(HSO4)K(H2SO4)5(H2O)x–H2O xZ0 (1) 17.9 1 (1) 15.3 2 (1) 14.2 3 (1) 13.5 4 (1) 13.4 5 (1) 14.6 6 (1) 14.6 7 (1) 13.5

74.9 64.0 59.4 56.5 56.1 61.1 61.1 56.5

MS

(1) 1982ARN/VIG (2) 2003FRO/LOV

(3) Extrapolate

(3) This volume

MS

(1) 1982ARN/VIG (2) 2003FRO/LOV

(3) Extrapolate

(3) This volume

(1) MS

(1) 2003FRO/LOV

(continued)

7366—CHAPTER 26—5/2/2007—12:19—JEBA—15382—XML MODEL B – pp. 1243–1349

1336

Comprehensive Handbook of Chemical Bond Energies

Table 26.2.3 (continued) BDEs in Negative Sulfur-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 8 9 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) Extrapolate

(2) This volume

(1) 13.5 (1) 13.7 (2) w10.5

56.5 57.3 w44

(HSO4)K(H2SO4)6 (H2O)x–H2O xZ0 1 2 3

19.7 17.3 16.0 14.8

82.4 72.4 66.9 61.9

MS

2003FRO/LOV

(HSO4)K(HNO3)–H2O

13.0

54.4

MS

1982ARN/VIG

ðCH3 SOK 3 ÞðH2 OÞx –H2O xZ0 1 2

13.9G1.5 12.4G1.5 11.4G1.5

58.2G6.3 51.9G6.3 47.7G6.3

ES MS

1995BLA/KLA

ðCF3 SOK 3 ÞðH2 OÞx –H2O xZ0 1

11.6G1.5 10.8G1.5

48.5G6.3 45.2G6.3

ES MS

1995BLA/KLA

SFK 6 –H2O

10.5G0.1

43.9G0.4

HP MS

1986SIE

C6H5SK–H2O

11.4G0.2

47.7G0.8

HP MS

1989SIE/MEO

HSK–H2S

13.2

55.2

HP MS

1988MEO(d)

F5SK–H2S

51G12

213G50

Selected ion FA

1993ZAN/HAN

7366—CHAPTER 26—5/2/2007—12:19—JEBA—15382—XML MODEL B – pp. 1243–1349

BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1337

SK 2 ðCS2 Þx –CS2 xZ0 1

19.1 6.1

79.9 25.5

HP MS

1994HIR/FUJ

CSK 2 ðCS2 Þx –CS2 xZ0 1

21.9 6.4

91.6 26.8

HP MS

1994HIR/FUJ

(1) (2) (3) (2) (4) (2) (2) (2) (2) (2) (5) (5) (5) (6)

100.4 89.1G5.4 87.8G4.8 33.9G1.3 34.7 26.8G0.8 22.6G1.3 17.6G0.8 15.1G1.3 14.2G0.6 14.4G1.3 12.8G1.5 12.6G2.5 w24.9

(1) HP MS (2) Equilibrium (3) Photodetach.

(1) 1980KEE/LEE (2) 1994VAC/DUC (3) 2001LI/ALC

(4) Photodetach.

(4) 2002CLE/LUO

(5) HP MS

(5) 1992VAC/JOR

(6) Extrapolate

(6) This volume

(O2S)K(SO2)x–SO2 xZ0

1 2 3 4 5 6 7 8 9 N

24.0 21.3G1.3 21.0G1.2 8.1G0.3 8.3 6.4G0.2 5.4G0.3 4.2G0.2 3.6G0.3 3.4G0.2 3.45G0.3 3.05G0.35 3.0G0.6 w5.7

O2 SðH2 OÞðSO2 ÞK x –SO2 xZ1 2 3 4 5

6.6G0.2 6.0G0.2 4.5G0.6 4.3G0.7 3.2G0.6

27.6G0.8 25.1G0.8 18.8G2.5 18.0G2.9 13.4G2.5

Equilibrium

1994VAC/DUC

O2 SðH2 OÞ2 ðSO2 ÞK x –SO2 xZ3 4 5

4.0G0.2 3.8G0.9 3.7G0.7

16.7G0.8 15.9G3.8 15.5G2.9

Equilibrium

1994VAC/DUC

O2SK(O2)x(SO2)x–SO2 xZ1 2 3

5.7G0.6 4.6G0.4 3.6G0.4

23.8G2.5 19.2G1.7 15.1G1.7

HP MS

1992VAC/JOR

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 26.2.3 (continued) BDEs in Negative Sulfur-Ion Clusters/Complexes BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

O4SK–SO2

w14

w58.6

Est. by exp.

1980KEE/LEE

HO4SK–SO2

13.7

57.3

HP MS

1986KEE/CAS

SOK 3 –SO2 –CO2

13.3 6.5

55.6 27.2

HP MS

1980KEE/LEE

ðHSOK 4 ÞðH2 SO4 Þx –SO3 xZ0 1 2

25.1 22.8 20.3

105.0 95.4 84.9

Kinetics

2004ROS/FRO

HO4SK–H2O2

15.9

66.5

FA

1984BOH/FAH

HO4SK(HNO3)x–HNO3 xZ0 1

27.4 17.0

114.6 71.1

MS

2001LOV/CUR

HO4SK(H2SO4)x–HNO3 xZ1 2 3

16.1 15.9 16.9

67.4 66.6 70.7

MS

2001LOV/CUR

HSK–CH3OH

17

71.1

HP MS

1988MEO(d)

SFK 6 –CH3OH

12.0G0.1

50.2G0.4

HP MS

1986SIE

C6H5SK–CH3OH

13.4G0.1

56.1G0.4

HP MS

1989SIE/MEO

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BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1339

C6H11SK–CH3OH, (5,5-dimethyl-1,3dithiani ion)

14.8

61.9

ICR

1984CAL/ROZ

(HO4S)K–HOSO2

O22.4

O93.7

MS

1984ARN/QIU

(HO4S)K(HONO2)– HOSO2

21.7

90.8

MS

1984ARN/QIU

(HSO4)K(H2SO4)x–HSO3 xZ1 (2) 22.1 2 (1) O18.0 (2) 21.0

92.5 O75.3 87.9

MS

(1) 1982ARN//VIG (2) 1984ARN/QIU

HO3SK(H2O)–H2SO4

22.1

92.5

MS

1984ARN/QIU

(1) (1) (2) (1) (2) (3) (1) (3) (1) (3)

175 115 92.0 99.6 87.0 82.8 90.4 77.4 85.4 79.1

MS

(1) 2001LOV/CUR

HO4SK(H2SO4)x–H2SO4 xZ0 1 2

3 4

41.8 27.4 22.0 23.8 20.8 19.8 21.6 18.5 20.4 18.9

(2) 1984ARN/QIU

(3) 1982ARN/VIG

HS2 OK 7 ðH2 SO4 Þx –H2SO4 xZ1 2

23.4 21.1

97.9 88.3

Kinetics

2004ROS/FRO

SFK 5 –SF6 SFK 6 –SF6

!2.3 w2.3

!9.6 w9.6

HP MS

1995HIR/SHI

SFK 6 –C2H5OH

12.5G0.1

52.3G0.4

HP MS

1986SIE (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 26.2.3 (continued) BDEs in Negative Sulfur-Ion Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

HSK–C2H5OH HSK–CF3CH2OH C6H5SK–CF3CH2OH

16.3G0.1 26.8G0.5 21.0G0.2

68.2G0.4 112.1G2.1 87.9G0.8

HP MS

1989SIE/MEO

CH3SK–i-C3H7OH C6H5SK–i-C3H7OH

17.1G0.2 15.0G0.1

71.5G0.8 62.8G0.4

HP MS

1989SIE/MEO

SFK 6 –i-C3H7OH

13.4G0.1

56.1G0.4

HP MS

1986SIE

HSK–B, BZt-C4H9OH C6H5SK–B

16.8G0.3 14.6G0.1

70.3G0.8 61.1G0.4

HP MS

1989SIE/MEO

SFK 6 –t-C4H9OH –MeSO

14.1G0.1 14.7G0.1

59.0G0.4 61.5G0.4

HP MS

1986SIE

C6H5SK–MeC(O)OH –EtC(O)OH

20.3G0.1 20.0G0.4

84.9G0.4 83.7G1.7

HP MS

1989SIE/MEO

HSK–pyrrole –CH3C(O)NHCH (CH3)–C(O)OCH3

23.0 27.5

96.2 115.1

HP MS

1988MEO(d)

SFK 6 –3-CF3C6H4NO2 –3-FC6H4NO2 –benzoquinone

17.0 15.7 14.9

71.7 65.7 62.3

IMRB

1986CHO/KEB

HSK–B, BZFe(CO)5 MeSK–B

R23.1 R28.6

R97 R120

Ion reactions

1985LAN/SAL

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BDEs in the O-, S-, Se-, Te-Clusters and Complexes

SO2K 2 ðH2 OÞx –H2O xZ3 4 5 6

7

8

9

10

11

N

(1) (2) (1) (2) (1) (2) (1) (2) (3) (1) (2) (3) (1) (2) (3) (1) (2) (3) (1) (2) (3) (1) (2) (3) (4)

13.8G1.2 12.0 8.8G1.2 10.1 8.5G1.2 8.1 8.1G1.2 8.5 13.9 7.6G1.2 6.9 12.4 6.0G1.2 6.9 11.8 5.5G1.2 6.5 10.9 4.4G1.2 4.6 10.9 4.4G1.2 4.2 10.7 w10.5

57.9G4.8 50.2 36.7G4.8 42.5 35.7G4.8 33.8 33.8G4.8 35.7 58.2 31.8G4.8 28.9 51.9 25.1G4.8 28.9 49.4 23.2G4.8 27.0 45.6 18.3G4.8 19.3 45.6 18.3G4.8 17.4 44.8 w44

1341

(1) PES (2) Photodetach.

(1) 2000WAN/NIC (2) 2002YAN/WAN

(3) ES MS

(3) 2005BLA/KEB

(4) Extrapolate

(4) This volume

26.3 Selenium clusters/complexes Table 26.3 BDEs in Selenium Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

H2Se–H2Se

3.1

13.0

Spectroscopy

1990SEN/RAL

SeC–Se

(1) 100.9 (2) 98.6G4.6

422.2 413G19

(1) 1979HUB/HER (2) 1996NIST

(3) 99.6

416.8

(1) Review (2) Derived from IP in ref. (3) PD

(3) 2000BRE/CAH (continued)

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Table 26.3 (continued) BDEs in Selenium Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

SeC(Se)x–Se xZ1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19

40.8 56.7 96.9 52.1 58.6 57.9 54.4 52.3 52.1 52.6 51.7 58.3 54.4 54.9 53.7 53.5 53.0 53.0 55.8

170.8 237.3 405.2 218.1 245.1 242.2 227.7 219.0 218.1 220.0 216.1 244.1 227.7 229.6 224.8 223.8 221.9 221.9 233.5

PD

2000BRE/CAH

SeC(Se)x–Se2 xZ0 1 2 3 4 5 6 7 8 9 10 11 12 13 14

60.4 17.8 73.8 69.2 30.9 36.7 32.3 26.7 27.0 24.9 24.2 30.0 32.7 29.5 28.6

252.8 74.3 308.7 289.4 129.3 153.4 135.1 111.9 112.9 104.2 101.3 125.4 137.0 123.5 119.6

PD

2000BRE/CAH

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BDEs in the O-, S-, Se-, Te-Clusters and Complexes

15 16 17 18

1343

27.4 26.7 26.3 28.8

114.8 111.9 110.0 120.6

SeC(Se)x–Se3 xZ0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17

69.4 66.9 77.9 79.8 40.8 43.1 36.9 31.1 29.3 28.6 34.8 36.7 39.9 35.3 34.4 32.7 32.1 34.1

290.4 279.8 326.1 333.8 170.8 180.4 154.4 130.3 122.5 119.6 145.7 153.4 166.9 147.6 143.8 137.0 134.1 142.8

PD

2000BRE/CAH

SeC(Se)x–Se4 xZ0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16

111.8 64.6 82.1 83.2 39.2 39.4 33.0 30.0 24.9 30.9 33.2 35.5 37.4 32.7 31.4 29.5 31.6

467.9 270.2 343.5 348.3 164.0 165.0 138.0 125.4 104.2 129.3 138.9 148.6 156.3 137.0 131.2 123.5 132.2

PD

2000BRE/CAH

(continued)

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Table 26.3 (continued) BDEs in Selenium Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

SeC(Se)x–Se5 xZ0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15

97.1 56.3 73.1 70.8 26.3 26.3 18.0 14.1 20.3 20.1 22.6 23.8 25.8 22.8 21.4 22.4

406.2 235.4 305.9 296.2 110.0 110.0 75.3 58.9 84.9 83.9 94.6 99.4 108.1 95.5 89.7 93.6

PD

2000BRE/CAH

SeC(Se)x–Se6 xZ0 1 2 3 4 5 6 7 8 9

98.9 57.4 70.8 66.4 19.4 22.1 15.2 13.4 18.0 18.2

413.9 240.2 296.2 277.9 81.0 92.6 63.7 56.0 75.3 76.2

PD

2000BRE/CAH

19.6 20.8 19.8 16.8 18.2

82.0 86.8 83.0 70.4 76.2

102.8

430.3

PD

2000BRE/CAH

10 11 12 13 14

SeC(Se)x–Se7 xZ0

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BDEs in the O-, S-, Se-, Te-Clusters and Complexes

1 2 3 4 5 6 7 8 9 10 11 12 13

1345

57.7 69.2 64.6 18.0 19.8 19.6 13.8 17.1 20.1 22.1 21.9 21.2 20.3

241.2 289.4 270.2 75.3 83.0 82.0 57.9 71.4 83.9 92.6 91.7 88.8 84.9

104.0 56.7 68.0 63.9 18.7 24.9 20.8 18.2 19.1 21.2 21.0 19.6 23.5

435.1 237.3 284.6 267.3 78.2 104.2 86.8 76.2 80.1 88.8 87.8 82.0 98.4

PD

2000BRE/CAH

SeC–S

(1) 101G4.8 (2) 93.8G4.6

423G20 392G19

(1) MS (2) Derived from IP in ref.

(1) 1983GRA/WIE (2) 1996NIST

SeC–H

72.6

304

Derived from IP in ref.

1996NIST

SeC–F

87G10

364G42

Derived

1974GUR/KAR

SeC–P

123G6

514G25

Derived from IP in ref.

1996NIST

SeC(Se)x–Se8 xZ0 1 2 3 4 5 6 7 8 9 10 11 12

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 26.3 (continued) BDEs in Selenium Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(CH3)2Se.C–Se(CH3)2

w22.7G0.7

w95G3

CID

2003KIN/ILL

SeK–Se

77.1

323

1996NIST

–H

79.1

331

Derived from DfH0 in ref.

25.1G2.3

105G9.6

Collision ionization

1978COM/REI

SeFK 5 –F

26.4 Tellurium clusters/complexes Table 26.4 BDEs in Tellurium Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) TeC–Te

TeC(Te)x–Te xZ1 2 3 4 5 6 7 8 9 10 11 12

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 78.4 (2) 82 (3) 66.4G6.9

328 342 278G29

(1) Derived (2) Review (3) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996SMI/YAT (3) 1996NIST

29.5 53.5G6 58.3 42.7 48.2 51.2 40.8 42.0 45.2 46.1 45.0 45.7

123.5 223.8G25 244.1 178.5 201.6 214.2 170.8 175.6 189.1 193.0 188.1 191.0

Evaporation

1995BRE/CAH

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BDEs in the O-, S-, Se-, Te-Clusters and Complexes

13 14 15 16 17 18 19 20 23 28 33

1347

45.7 43.8 43.8 44.7 45.0 45.0 45.2 45.2 45.2 45.4 45.7

191.0 183.3 183.3 187.2 188.1 188.1 189.1 189.1 189.1 190.1 191.0

TeC(Te)x–Te2 xZ0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 22 27 32

46.1 27.2 49.8G6 39.2 29.1 37.6 30.2 21.0 25.4 29.5 29.3 28.8 29.5 27.7 25.8 26.7 27.9 28.1 28.4 28.6 28.6 29.1 29.5

193.0 113.8 208.4G25 164.0 121.6 157.3 126.4 87.8 106.1 123.5 122.5 120.6 123.5 115.8 108.1 111.9 116.7 117.7 118.7 119.6 119.6 121.6 123.5

Evaporation

1995BRE/CAH

TeC(Te)x–Te5 xZ0 1 2 3 4 5 6

O66 33.4 48.7G6 36.2 19.8 22.4 20.3

O276 139.9 203.6G25 151.5 83.0 93.6 84.9

Evaporation

1995BRE/CAH

(continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 26.4 (continued) BDEs in Tellurium Clusters/Complexes

The broken bonds (boldfaceZdissociated fragment) 7 8 9 10 11 12 13 14 15 16 19 24 29

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

14.1 18.9 22.6 21.2 18.9 19.1 18.7 18.0 19.4 20.8 20.8 21.4 22.4

58.9 79.1 94.6 88.8 79.1 80.1 78.2 75.3 81.0 86.8 86.8 89.7 93.6

TeC(Te)x–Te6 xZ2 3 4 5 6 7 8 9 10 11 12 13 14 15 19 24 29

44.5G6 33.0 19.8 23.3 20.1 14.5 19.1 21.2 19.8 18.9 19.1 18.4 18.0 19.4 20.5 21.4 22.8

186.2G25 138.0 83.0 97.4 83.9 60.8 80.1 88.8 83.0 79.1 80.1 77.2 75.3 81.0 85.9 89.7 95.5

Evaporation

1995BRE/CAH

TeC(Te)x–Te7 xZ2 3 4 5 6 7

44.3G6 36.2 24.9 26.3 23.8 19.1

185.2G25 151.5 104.2 110.0 99.4 80.1

Evaporation

1995BRE/CAH

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BDEs in the O-, S-, Se-, Te-Clusters and Complexes

8 9 10 11 12 13 14 17 22 27

1349

21.0 23.8 23.5 22.8 22.1 21.7 20.8 22.8 23.5 O27.7

87.8 99.4 98.4 95.5 92.6 90.7 86.8 95.5 98.4 O116

TeC–H

72.8G2.9

305G12

Derived from IP in ref.

1996NIST

TeC–O

(1) 96.6 (2) 81G12

404 339G50

(1) Derived (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

(2) 81.9G4.6 (3) 79.6G4.8

342G19 333G20

TeC–P

99G23

415G97

Derived from IP in ref.

1996NIST

(CH3)2Te%C–Te(CH3)2

23.2G0.5

97G2

Tandem MS

2004KIN/ILL

TeK–Te

60.4G1.5

252.7G6.3

Derived from EA in ref.

1996NIST

74.1G1.6

310.2G6.7

–Se

–H

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chapter twenty-seven

BDEs in the halogenated molecules, clusters and complexes 27.1 F–, F +–, and F ––X bonds 27.1.1 F–X bonds Table 27.1.1 BDEs of F–X Bonds

The broken bonds (boldfaceZ dissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

F–F

(1) 37.95 (2) 37.923G0.023

158.78 158.670G0.096

(1) Spectroscopy (2) PEI-ZEKE

(1) 1979HUB/HER (2) 2005YAN/HAO

F–Cl

(1) 61.24 (2) 61.25

256.23 256.25

Spectroscopy

(1) 1974NOR (2) 1997ALE/SET

F–Br

(1) 60.6 (2) 66.9G2.8

253.5 280G12

Spectroscopy

(1) 1976CLY/CUR (2) 1990JEY/RAJ

F–I

%64.9

%271.5

Spectroscopy

1976CLY/MCD

HF–He DF–He

0.02, at 0 K 0.02

0.08 0.08

Spectroscopy

1990lOV/NES

(continued)

1351

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Table 27.1.1 (continued) BDEs of F–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated atom)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

HF–Ar

0.29, at 0 K

1.22

IR

1986FRA/PIN

F–Kr

1.6

6.6

Spectroscopy

1994LO/SET

HF–Kr

0.38, at 0 K

1.59

IR

1986FRA/PIN

F–Xe

(1) 3.77 (2) 3.39

15.77 14.18

Spectroscopy

(1) 1981RAO/RED (2) 1994JOH/TEL

HF–Xe

0.52, at 0 K

2.16

IR

1986FRA/PIN

F–H

(1) 136.23 (2) 136.202G0.014 (3) 136.152G0.003 (4) 136.157G0.003

569.98 569.870G0.060 569.658G0.012 569.680G0.011

(1) (2) (3) (4)

F–D

(1) 137.8 (2) 137.709G0.023 (3) 137.724G0.003 (1) 138.5 (2) 138.387G0.026

576.6 576.174G0.096 576.236G0.011 579.5 579.009G0.108

(1) Spectroscopy (2) Spectroscopy (3) TIPPS

(1) 1979HUB/HER (2) 1993ZEM/STW (3) 2006HU/HEP

F–BrF –BrBr –BrF2

106.6 83.9 22.6

446.0 351.0 94.6

Derived from DfH0 from ref.

1996NIST

(ortho)D2–HF (para)D2–HF

0.146G0.006, 0 K 0.194G0.006

0.610G0.024 0.813G0.024

Photofrag.

1993BOH/MIL

–T

Spectroscopy Spectroscopy TIPPS TIPPS

7366—CHAPTER 27—5/2/2007—09:52—JEBA—15383—XML MODEL B – pp. 1351–1427

(1) (2) (3) (4)

1979HUB/HER 1993ZEM/STW 2000MAR/HEP 2006HU/HEP

BDEs in the Halogenated Molecules, Clusters and Complexes

(HF)x–HF xZ1

2 3 4 5 6

(1) (2) (3) (4)

4.3, at 0 K 3.0 4.5 6.2

18 12.7 18.9 26.1

(5) (4) (4) (4) (4) (4)

4.6G0.1 7.9 7.5 7.8 10.7 5.2

19.1G0.2 33.1 31.4 32.6 44.7 21.7

(1) (2) (3) (4)

1353

Review Spectroscopy Near-IR Derived from DfH0 from ref. (5) Review

(1) (2) (3) (4)

1984BEY/KAR 1992BOH/MAR 1996AND/DAV 1996NIST

(5) 1998KLO/QUA

DF–HF HF–DF

3.094G0.006, 0 K 3.308G0.006

12.944G0.024 13.841G0.024

Photofrag.

1997OUD/MIL

(DF)2–DF

O7.79, at 0 K

O32.59

Spectroscopy

1993SUH/FAR

HF–HCl

1.835G0.006, 0 K

7.680G0.024

Photofrag.

1995OUD/MIL

HF–N2

5.98 4.76G0.02 6.58 7.06

(1) Spectroscopy (2) Photofrag. (3) IR

(1) 1993NES/CHI (2) 1994BEM/BOH (3) 1994NES/LIN

DF–N2

(1) (2) (3) (3)

HF–NO

1.281G0.014, 0 K

5.359G0.069

Photofrag.

1992SHO/CAS

HF–OC

2.09G0.025, 0 K

8.76G.1.04

Photofrag.

2000OUD/MIL

HF–H2O

6.2, at 0 K

25.9

IR

1975THO

HF–OCO

1.93G0.01, 0 K

8.06G0.05

Photofrag.

1998OUD/MIL

HF–HCN

(1) 6.2, at 0 K (2) 5.4G0.1 (3) 5.63G0.03

26.1 22.6G0.2 23.57G0.12

(1) Spectroscopy (2) Spectroscopy (3) Photofrag.

(1) 1980LEG/MIL (2) 1987WOF/ELI (3) 1998OUD/MIL

1.43, at 0 K 1.14G0.01 1.57 1.69

(continued)

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1354

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.1 (continued) BDEs of F–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated atom)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

HF–CH3CN HF–HCCCN

6.2G0.1, at 0 K 4.9G0.2

26.1G0.6 20.4G0.7

FT-IR

1987LEG/MIL

F–ClO3

57

238

EI

1957DIB/REE

HF–O(CH2)2

5.48, at 0 K

22.9

FT-IR

2005ASS/GOU

HF–S(CH2)2

5.56, at 0 K

23.3

FT-IR

2004ASS/GOU

HF–C2H2

3.11G0.01, 0 K

13.02G0.02

Photofrag.

1999OUD/MOO

HF–C6H6

1.43, at 0 K

5.98

Spectroscopy

1995BET/BET

HF–CH3OCH3 –CH3OC2H5 –C2H5OC2H5

10.3 8.84 7.17

43.1 37.0 30.0

IR

1971THO

0.84–3.7

3.5–15.5

TR-NMR

2004TAK/KOT

H-bond in intramolecule H O F

7366—CHAPTER 27—5/2/2007—09:52—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1355

27.1.2 F+–X bonds Table 27.1.2 BDEs of F+–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated atom)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

F+–F

(1) 77.3G2.0 (2) 77.771G0.023

323.4G8.4 325.393G0.096

(1) Derived (2) PEI-ZEKE

(1) 1974GUR/KAR (2) 2005YAN/HAO

F+–He

43.41G0.02

181.62G0.08

Derived

1974GUR/KAR

FC–Ar

38.5

161.1

Ion reaction

1979HUB/HER

F+–Kr

36.4

152.4

Review

1979HUB/HER

F+–Xe

45.0

188

CID

2003KRO/WEN

HF+–HF

(1) 33 (2) R33.0

138 R138

(1) PI (2) PES

(1) 1979TIE/AND (2) 1988TOM

25.1 14.8

105 61.9

PI

1979TIE/AND

(H2F)+(HF)x–HF xZ0 1

27.1.3 FK–X bonds Table 27.1.3 BDEs of FL–X Bonds

The broken bonds (boldfaceZ dissociated atom) FK–F

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) 29G2 (2) 28.6G1.6 (3) 28.81G0.0.1

kJ/mol 121.3G8 119.6G6.7 120.55G0.04

Methods (reference in parentheses) (1) Derived (2) CID (3) Derived from EA in ref.

References (1) 1974GUR/KAR (2) 1995WEN/SQU (3) 1996NIST (continued)

7366—CHAPTER 27—5/2/2007—09:53—JEBA—15383—XML MODEL B – pp. 1351–1427

1356

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.3 (continued) BDEs of FK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated atom)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

FK–Cl –I

18.5G7 9.5G5

77.4G29 40G21

Derived from EA in ref.

1996NIST

FK–Li

90.6G5

379G21

Derived from EA in ref.

1996NIST

FK–Na

(1) 48.9G2.5 (2) 71.0G4.6

204.5G10.6 297G19

(1) PES (2) Derived from EA in ref.

(1) 1986MIL/LEO (2) 1996NIST

FK–K

62.5G5

261G21

Derived from EA in ref.

1996NIST

(1) 88.4G9 (2) 87.2G10

370G38 365G42

(1) Ion reactions (2) Derived from EA in ref.

(1) 1991BOL/BOR (2) 1996NIST

(1) 82.0G8.4 (1) 86.3G3.8 (1) 92.5G3.5 (1) 98.2G9.6

343G35 361G16 387G15 411G40

FK–Xe

6.5

27.2

Scattering

1979VRE/RES

FK–O

(1) 26.7G3.5 (2) 26.5G1.0

111.8G14.5 111.0G4.2

(1) Derived (2) Derived from EA in ref.

(1) 1992GIL/POL (2) 1996NIST

FK–S

(1) 65G10 (2) 56.4G2.0

272G42 235.8G8.4

(1) Derived (2) Derived from EA in ref.

(1) 1992GIL/POL (2) 1996NIST

FK–CrFx xZ0

1 2 3 4

7366—CHAPTER 27—5/2/2007—09:53—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1357

FK–Se

65G10

272G42

Derived

1992GIL/POL

FK–N

16.5G2.4

69.1G10

Derived from EA in ref.

1996NIST

FK–P

53G17

222G71

Derived

1999GUR/LES

FK–As

49.5G2.5

207G11

Derived from EA in ref.

1996NIST

FK–C

120.4G7.4

504G31

Derived from EA in ref.

1996NIST

FK(F)x–Si xZ0 1 2 3

78.9G0.5 84.2G2.3 82.3G5.1 %88.3

330.0G1.9 352G10 344G21 %370

PES

1996KAW/NEG

FK–F2

23.5G2.5

98.4G10.6

CID

2000ART/NIZ

FK–HF

(1) 38.5 (2) 45.8G1.6

161.1 191.6G6.7

(1) ICR (2) CID

(1) 1983LAR/MCM (2) 1995WEN/SQU

FK–HCl

(1) 50 (2) 60G2

209 251G8

(1) Derived (2) ICR

(1) 1971YAM/KEB (2) 1985LAR/MCM

FK(Be2F4)–NaF

65.2G2.5

273G11

Ion reactions

1980NIK/SOR

FK–KF

53.5G0.8

223.8G3.3

MS

1981NIK/SID

FK(Be2F4)–KF

69.2G2.5

290G11

Ion reactions

1980NIK/SOR (continued)

7366—CHAPTER 27—5/2/2007—09:53—JEBA—15383—XML MODEL B – pp. 1351–1427

1358

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.3 (continued) BDEs of FK–X Bonds

The broken bonds (boldfaceZ dissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

FK(AlF3)–KF

28.6G2

119.7G8.4

Ion reactions

1980NIK/SOR

FK–U(F)x xZ0

102.8G12

430G50

1985HIL/GUV

145G18.5 140G18.5 148G17 153G14.5

607G77 586G77 619G71 640G61

Derived from DfH0 in ref

FK(O2)x–O2 xZ0 1 2 N

(1) 2.6G0.2 (1) 2.5G0.2 (1) w1.8 (2) w1.6

10.9G1.3 10.5G0.8 w7.5 w6.8

(1) HP MS

(1) 1998HIR/NAS

(2) Extrapolate

(2) This volume

FK(N2)x–N2 xZ0 1

4.5G0.2 2.8G0.2

18.8G1.3 11.7G0.8

HP MS

1998HIR/NAS

FK–P2

34.4G2.5

144G10

Ion reactions

1992OHA/KRE

FK(NO)x–NO xZ0 1 2

8.3G0.2 8.2G0.2 4.6G0.2

34.7G0.8 34.3G0.8 19.2G0.8

HP MS

1986HIR/NAS

(1) 46.6G3.6 (2) 51.1G2.3

195G15 214G10

(1) Ion reactions (2) PES

(1) 1988MUR/LEO (2) 1999SCH/DAV

(1) 9.8G0.2 (1) 6.3G0.2

41.0G0.8 26.4G0.8

(1) HP MS

(1) 1998HIR/NAS

1 2 3 4

FK–CF

FK(CO)x–CO xZ0 1

7366—CHAPTER 27—5/2/2007—09:53—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

2 3 4 5 N

(1) (1) (1) (1) (2)

5.5G0.2 5.0G0.2 2.9G0.2 2.5G0.2 w1.8

23.0G0.8 20.9G0.8 12.1G0.8 10.5G0.8 w7.5

1359

(2) Extrapolate

(2) This volume

FK–BeF2

(1) 97.3G2.3 (2) 90

407G10 377

MS

(1) 1980NIK/SOR (2) 1982SID/BOR

FK(Be2F4)–BeF2 FK(AlF3)–BeF2

41.8G2.5 43.5G2.5

174.9G10.5 182.0G10.5

MS

1980NIK/SOR

FK–FBO

50

209

ICR

1987LAR/MCM(b)

FK(CO2)x–CO2 xZ0

(1) (2) (3) (2) (2) (2) (2) (2) (2) (4)

31.7 32.3 30.2G9.3 7.3 7.2 5.8 5.6 5.3 w3.9 w5.7

132.6 135.1 126G39 30.5 30.1 24.3 23.4 22.2 w16.3 w24

(1) ICR (2) HP MS (3) Photodetach.

(1) 1985LAR/MCM (2) 1987HIR/MIZ(b) (3) 1995ARN/BRA

(4) Extrapolate

(4) This volume

FK(N2O)x–N2O xZ0 1 2 3 4 5 6 N

(1) (1) (1) (1) (1) (1) (1) (2)

9.87G0.3 9.23G0.3 8.42G0.3 7.40G0.3 6.33G0.3 6.03G0.3 3.3G0.3 w4

41.3G1.3 38.6G1.3 35.2G1.3 31.0G1.3 26.5G1.3 25.2G1.3 13.8G1.3 w17

(1) HP MS

(1) 1993HIR/ARU

(2) Extrapolate

(2) This volume

FK–HNO

33.0G3

138G13

FT MS

1997JAN/ZHO

FK–HCN

39.5

165.3

ICR

1983LAR/MCM

1 2 3 4 5 6 N

(continued)

7366—CHAPTER 27—5/2/2007—09:53—JEBA—15383—XML MODEL B – pp. 1351–1427

1360

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.3 (continued) BDEs of FK–X Bonds

The broken bonds (boldfaceZ dissociated atom) FK–AsFO –AsFS

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

54G7 56G6

226G29 234G25

ICR

1997LAR/MCM(b)

(1) 23.3 (2) 26.2G0.8 (1) 16.6 (3) 19.2G0.5 (1) 13.7 (3) 15.3G0.4 (1) 13.5 (3) 13.9G0.4 (1) 13.2 (3) 12.3G0.4 (3) 10.9G0.3 (3) 10.4G0.3 (2) 11.2G0.4 (2) 11.1G0.5 (2) w11 (4) w10.5

97.5 109.6G3.3 69.5 80.3G2.1 57.3 64.0G1.7 56.5 58.2G1.7 55.2 51.5G1.7 45.6G1.3 43.5G1.3 46.9G1.7 46.4G2.1 w46 w44

Equilibrium

(1) 1970ARS/YAM (2) 1999WEI/KEM

(4) Extrapolate

(4) This volume

FK–D2O

23.0G2.0

96.2G8.4

ICR

1988LAR/MCM

FK–H2S

34.6

144.8

ICR

1983LAR/MCM

FK–SO2

(1) %46G2 (2) 43.8 (3) O59 (4) 53.0G2.5 (5) 53.8G2.2

%192G8 183.3 O247 221.8G10.5 225G9

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

FK–COS

31.8

133.1

ICR

FK(H2O)x–H2O xZ0 1 2 3 4 5 6 7 8 9 N

(3) 1988HIR/MIZ

ICR ICR MS CID CID

7366—CHAPTER 27—5/2/2007—09:53—JEBA—15383—XML MODEL B – pp. 1351–1427

1977MUR/BEA 1983LAR/MCM 1986KEE/CAS 1992SQU(b) 2003LOB/CHE(b)

1985LAR/MCM

BDEs in the Halogenated Molecules, Clusters and Complexes

FK(SCO)x–SCO xZ1 2 3

FK(CS2)x–CS2 xZ0 1 2

1361

7.0G0.3 5.6G0.3 5.1G0.3

29.3G1.3 23.4G1.3 21.3G1.3

HP MS

2004HIR/FUJ

(1) (2) (2) (2)

131.0 146.4G6.3 28.1G0.8 w23

(1) ICR (2) HP MS

(1) 1985LAR/MCM (2) 1993HIR/FUJ

31.3 35.0G1.5 6.71G0.2 w5.4

FK–SSO

44.0G3.0

184G14

ICR

1987LAR/MCM(b)

FK–FPS

62G5

259G21

ICR

1987LAR/MCM

FK–SiF2

67

280

ICR

1987LAR/MCM(b)

(1) 93.4G2.0 (2) 83.9G3.8 (1) 49.1G2.0

390.8G8.4 351G16 205.4G8.4

MS

(1) 1982SID/GUB (2) 1992BOL/BOR

FK(FeF2)x–FeF2 xZ0 1

(1) 87.7G3.6 (2) 48.3G8.8

367G15 202G37

MS

(1) 1992BOL/BOR (2) 1986SID/BOR

FK(FeF3)–FeF2

50.4

211

MS

1986SID/BOR

FK–NiF2

80.8G3.6

338G15

MS

1992BOL/BOR

FK–CuF2

83.8G4.1

351G17

MS

1986KUZ/KOR

FK–ZnF2

80.5G4.5

337G19

MS

1986NIK/IGO

FK(MnF2)x–MnF2 xZ0 1

(continued)

7366—CHAPTER 27—5/2/2007—09:53—JEBA—15383—XML MODEL B – pp. 1351–1427

1362

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.3 (continued) BDEs of FK–X Bonds

The broken bonds (boldfaceZ dissociated atom)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

FK(YF3)x–YF3 xZ0 1

114G5 56G5

477G21 234G21

MS

1981PYA/GUS(b)

FK(ScF3)x–ScF3 xZ0 1

(1) 113.3G3.6 (2) 54.5G0.2

474G15 228.0G0.8

MS

(1) 1992BOL/BOR (2) 1981NIK/SID

FK–CeF3

109.7G7

459G29

MS

1981SID/SOR

FK–MnF3

100.6G3.1

421G13

MS

1984CHI/KOR

FK–FeF3

109.0G3.3

456G14

MS

1984CHI/KOR

FK–CoF3

105.7G6

442G25

MS

1997RAU/CHI

FK(AlF3)x–CoF3

55G12

230G50

MS

1987SID/NIK

FK–RhF3

95.8G3.4

401G14

MS

1984CHI/KOR

FK–AuF3

101.8G6.0

426G25

MS

1986CHI/KOR

FK–BOF2

48.0G4

201G17

ICR

1983LAR/MCM(b)

FK–BF3

(1) 72.0G5 (2) 79.1G2 (3) 78.5G3.3

301G21 331G8 328G14

(1) ICR (2) Ion reactions (3) Ion reactions

(1) 1985LAR/MCM (2) 1991VEL/NES (3) 1996ALE/BOR

7366—CHAPTER 27—5/2/2007—09:53—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

FK–BCl3

FK(AlF3)x–AlF3 xZ0

1

1363

O85G10

O356G42

Ion reactions

1973HAA/MCD

(1) (2) (3) (4) (1) (3)

490 498G6.7 477 488G7.9 204 234

MS

(1) (2) (3) (4)

117.2 119.0G1.6 114 116.6G1.9 48.8 56

1979NIK/SKO 1980SID/NIK 1981PYA/GUS 1986NIK/IGO

FK–AlFCl2 –AlF2Cl –AlCl3

119.3G2.9 117.4G2.9 120.9G3.0

499G12 491G12 506G13

Ion reactions

1992PER/KOR

FK(AlF3)–GaF3

48.3G4.2

202G18

MS

1985ZHU/NIK

FK(GaF3)x–GaF3 xZ0 1

110.2G4.1 51.9G4.7

461G17 217G20

MS

1985ZHU/NIK

FK–SO3

(1) 78G10 (2) 81.6G3.3

326G42 341G14

(1) ICR (2) Ion reactions

(1) 1985LAR/MCM (2) 1992VIG/HEN

FK–SF3

(1) 63.2G9.3 (2) 43.5G7.6 (3) 42.4G3.2

264G39 182G32 177G13

Ion reactions

(1) 1981BAB/STR (2) 1991VIG/MIL (3) 1995MIL/MIL

FK–SF4

(1) 43.8 (2) 54.9G2.3

183.3 230G10

(1) ICR (2) CID

(1) 1985LAR/MCM (2) 2003LOB/CHE

FK–SF5

42.7G2.8

178G12

CID

2003LOB/CHE

FK(SF6)x–SF6 xZ0 1

5.4 w4.0

22.6 w16.7

HP MS

1995HIR/SHI (continued)

7366—CHAPTER 27—5/2/2007—09:53—JEBA—15383—XML MODEL B – pp. 1351–1427

1364

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.3 (continued) BDEs of FK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated atom)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

FK–SaOF2 –SaSF2 –SaSiF2

37.4 36.0G3 72

157 151G12.6 301

ICR

1983LAR/MCM(b)

FK–NH3

!23

!96

FA

1973SPE/FER

FK–NF3

7.2G0.3

30.1G1.3

HP MS

1995HIR/SHI

FK–FNO2 –FPO2

8 90

34 377

ICR

1987LAR/MCM(b)

FK–PF3

(1) 40.2 (2) 47.8G2.4

168 200G10

(1) ICR (2) Revised

(1) 1985LAR/MCM (2) 2002HEI/CHE

FK–AsF3

48.2

202

ICR

1985LAR/MCM

FK–HC(O)H

35.3

148

ICR

1983LAR/MCM

FK–FC(O)F

(1) 42.6G2.0 (2) 44.3G2.6

178G8.4 185G11

(1) ICR (2) Review

(1) 1983LAR/MCM (2) 1996HUE/DUN

FK–FSi(O)F

102G17

427G71

ICR

1983LAR/MCM(b)

FK–SiOF2

105

439

ICR

1987LAR/MCM(b)

FK–FC(O)H

O18.1

O75.7

Ion reactions

1977KAR/KLE

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1365

FK(AlF3)–BeF2NaF –BeF2KF

45.9G2.0 45.8G2.0

192.0G8.4 191.6G8.4

MS

1980SID/NIK

FK(Be2F4)–BeF2KF

44.9G2.0

188G8.4

MS

1980NIK/SOR

FK–ThF4

104.2G3.5

436G15

MS

1983SID/ZHU

FK–UF4

100.9G3.6

422G15

MS

1992BOL/BOR

FK–TiF4

86.3G3.8

361G16

MS

1992BOL/BOR

FK–ZrF4

51.2G1.0

214.2G4.2

MS

1982SKO/SOR

FK–HfF4

102.5G4

429G17

MS

1986NIK/IGO

FK–VF4

87.2G5.8

365G24

MS

1989KUZ/KOR

FK–MoF4

91.5G3.3

383G14

MS

1988BOR/BOL

FK–WF4

64.6

270

MS

1973THY/HAR

FK–MnF4

83G20

347G84

MS

1984KOR/CHI

FK–RuF4

97.0G4.2

406G18

MS

1989KUZ/KOR

FK–OsF4

87.0G6.4

364G27

MS

1989KUZ/KOR

FK(CH4)x–CH4 xZ0 1

(1) 6.7G0.2 (1) 5.9G0.2

28.0G0.8 24.7G0.8

(1) HP MS

(1) 2001HIR/MIZ (continued)

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

1366

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.3 (continued) BDEs of FK–X Bonds

The broken bonds (boldfaceZ dissociated atom) 2 3 4 5 6 7 8 9 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) Extrapolate

(2) This volume

(1) 5.5G0.2 (1) 5.0G0.2 (1) 4.5G0.2 (1) 4.2G0.2 (1) 3.3G0.2 (1) 2.9G0.2 (1) 2.3G0.2 (1) 1.8G0.2 (2) w2

23.0G0.8 20.9G0.8 18.8G0.8 17.6G0.8 13.8G0.8 12.1G0.8 9.6G0.8 7.5G0.8 w8

FK(CF4)x–CF4 xZ0 1 2 3 4 N

(1) 6.4 (1) 5.9 (1) 4.1 (1) 3.9 (1) w2.4 (2) w2.8

26.8 24.7 17.2 16.3 w10 w12

(1) HP MS

(1) 1995HIR/NAS

(2) Extrapolate

(2) This volume

FK–CHF3

27.1

113.4

ICR

1983LAR/MCM

FK–CH2F2

(1) 50.8G2.9 (2) 55.9G2.7

213G12 234G11

(1) Derived (2) CID

(1) 1979BAR/SCO (2) 1991PAU/SQU

FK–CH2CO

(1) 44.7G3 (2) 35.3 (3) 44.5G3.9

187G13 148 186G16

(1) ICR (2) ICR (3) Derived

(1) 1980FAR/MCM (2) 1983LAR/MCM (3) 1995WEN/SQU

FK–HC(O)OH

45.3

190

ICR

1983LAR/MCM

FK(SiF4)x–SiF4 xZ0 1

(1) 60.0G4 (2) 9.6G0.3

251G17 40.2G1.3

(1) ICR (2) HP MS

(1) 1983LAR/MCM (2) 2000HIR/NAS

FK–GeF4

100G7

418G29

Ion reactions

1984MAL/ROS

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1367

FK–SiCl4 –GeCl4 –SnCl4

27.5G1.7 39.9G1.7 60.0G2.9

115G7 167G7 251G12

CID

2005HAO/KAS

FK–OaPF3

47.9

200.4

ICR

1985LAR/MCM

FK–SaPF3

32G10

134G42

Ion reactions

1971RHY/DIL

FK–SO2F2 –CFOCFO –CF3CFO –CF3CF2CFO –CF3COCF3

35.8 45.7 45.6 47.2 49.7

150 191 191 198 208

ICR

1985LAR/MCM

FK–FClO2 –FClO3 –F3ClO2 –F3ClO

33 24 31 30

138 100 130 126

ICR

1987LAR/MCM(b)

FK–Mo(O)F4

96.2G3

403G13

Ion reactions

1985BOR/SID

FK–S(O)F4

58.0G3

243G13

ICR

1987LAR/MCM(b)

(1) (2) (3) (4) (2) (5) (2) (5) (2) (2) (2) (2) (2) (2)

123.8 97.5 123.8G2.1 123G9 80.8 84.9G1.3 60.7 63.2G2.5 52.3 49.8 48.1 41.0 40.6 38.5

(1) (2) (3) (4)

(1) (2) (3) (4)

FK(CH3OH)x–CH3OH xZ0

1 2 3 4 5 6 7 8

29.6 23.3 29.6G0.5 29.4G2.2 19.3 20.3G0.3 14.5 15.1G0.6 12.5 11.9 11.5 9.8 9.7 9.2

ICR HP MS Photodetach CID

(5) HP MS

1983LAR/MCM 1991HIR/YAM(b) 1997YAN/LIN 1999DET/ERV

(5) 1999BOG/PES

(continued)

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

1368

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.3 (continued) BDEs of FK–X Bonds

The broken bonds (boldfaceZ dissociated atom) 9 10 11 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 8.8 (2) 8.6 (2) w8.5 (6) w8.7

36.8 36.0 w36 w37

(6) Extrapolate

(6) This volume

34.2

143

ICR

1983LAR/MCM

(1) 16.0 (2) 24.5 (1) 12.9 (2) 17.7 (1) 11.7 (2) 15.1 (1) 10.4 (2) 12.8 (1) 5.3 (2) 11.5 (2) 9.7 (2) w8.5 (3) w7.9

66.9 102.5 54.0 74.1 49.0 63.2 43.5 53.6 22.2 48.1 40.6 w36 w33

HP MS

(1) 1972YAM/KEB (2) 1994HIR/YAM

(3) Extrapolate

(3) This volume

FK–CF3CN –CF3CF2CN –CF3CF2CF2CN

29.2 30.1 30.8

122 126 129

ICR

1985LAR/MCM

FK–F2CCFH

(1) 24.3G6 (2) 26.3G2

102G25 110G8

(1) Derived (2) ICR

(1) 1976SUL/BEA (2) 1983LAR/MCM

FK–F2CCH2 –FHCCH2 –H2CCH2

26.7G5 15.6G4 6.3G3

112G21 65G17 26.4G12.6

Derived

1976SUL/BEA

FK–CF3CHF2

30.4

127

ICR

1983LAR/MCM

FK–CH3SH

FK(CH3CN)x–CH3CN xZ0 1 2 3 4 5 6 N

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1369

FK(MnF2)–AlF4Li

54.7G2.0

229G8.4

MS

1982SID/GUB

FK(AlF3)x–AlF4Na –AlF4K

39.6G2.2 35.1G1.5

166G9.2 147G6.3

MS

1980SID/NIK

FK–Be2F4

111G2

464G8

Ion reactions

1980NIK/SOR

(1) 108G6 (1) 46G10 (2) 56.6G7.2

452G25 192G42 237G30

Ion reactions

(1) 1976BEA

FK–WF6

69.0G5

289G21

ICR

1979GEO/BEA

FK–SOF4 –FPO6

58G2 56

243G8 234

ICR

1987LAR/MCM

FK–F2SiCH2 –F(CH3)SiCH2 –(CH3)2SiCH2

46G2 40G2 37G2

193G8 167G8 155G8

ICR

1990ALL/MCM

FK–PF5

(1) 85G10 (2) 78.6G3.3

356G42 329G14

(1) ICR (2) Ion reactions

(1) 1983LAR/MCM (2) 1996ALE/BOR

FK–AsF5

O85G10

O356G42

ICR

1973HAA/MCD

FK–TeF5

192G11

803G46

Ion reactions

1978COM/REI

FK–CH3SiF3

(1) 61.5 (2) 50.5

257 211

ICR

(1) 1977MUR/BEA (2) 1985LAR/MCM

FK–CF2HCH2F –CF3CH2NH2

26.5 28.1

111 118

ICR

1983LAR/MCM

FK–UFx xZ5 6

(2) 1984PYA/GUA

(continued)

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

1370

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.3 (continued) BDEs of FK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated atom) FK(L)x–L, LaCH3CH2OH xZ0

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(1) 31.5 (2) 32.4G0.5 (3) 32.5G2.2 (2) 20.6G0.3 (2) 15.6G0.1

132 135.6G2.1 136G9 86.2G1.3 65.2G0.4

(1) ICR (2) HP MS (3) CID

(1) 1983LAR/MCM (2) 1999BOG/PES (3) 1999DET/ERV

FK–CH2FCH2OH –CF3CH2OH

34.8 39.1

146 164

ICR

1983LAR/MCM

FK–(CHF2)2O –CH3COOH

36.0 44.1

151 185

ICR

1983LAR/MCM

FK–CH2CCH2

14.8G3.7

62G15

Derived

1984BAR/BUR

FK(C3H6)x–C3H6 xZ0 1 2 3 4 5 N

(1) 9.8G0.3 (1) 8.8G0.3 (1) 7.8G0.3 (1) 6.7G0.3 (1) 6.0G0.3 (1) 5.6G0.3 (2) w4

41.0G1.3 36.8G1.3 32.6G1.3 28.0G1.3 25.1G1.3 23.4G1.3 w17

(1) HP MS

(1) 2001HIR/KAT

(2) Extrapolate

(2) This volume

FK–CF2C(O)CHF2

27

113

ICR

1984LAR/MCM

FK–CH3C(O)CH3

O25.9

O108

Ion reactions

1983SHE/BOW

FK–n-C3H7OH

32.3

135

ICR

1983LAR/MCM

1 2

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

FK(i-C3H7OH)x–iC3H7OH xZ0

1 2

(1) (2) (3) (2) (2)

32.3 33.5G0.7 33.2G2.2 20.8G0.2 17.6G0.2

1371

135 140.2G2.9 139G9 87.0G0.8 73.6G0.8

(1) ICR (2) HP MS (3) CID

(1) 1983LAR/MCM (2) 1999BOG/PES ERV/ERV

FK–(CF3)2CHOH –(CH2F)2CHOH

47.0G2.0 37.8

197G8 158

ICR

1983LAR/MCM

FK–(CH3)3CF –(CH3)3CBr

22.3 22.3

93.3 93.3

ICR

1983LAR/MCM

FK–n-C4H9OH

32.2

135

ICR

1983LAR/MCM

(1) (2) (3) (2) (2)

139 139.7G2.9 137G9 92.0G1.7 76.6G4.2

(1) ICR (2) HP MS (3) CID

(1) 1983LAR/MCM (2) 1999BOG/PES (3) 1999DET/ERV

FK(L)x–L, LZtC4H9OH xZ0

1 2

33.3 33.4G0.7 32.7G2.2 22.0G0.4 18.3G1.0

FK–t-C4F9OH

56.3G2.0

236G8

ICR

1985LAR/MCM

FK–(CH3)3CCHO

24.6

103

ICR

1983LAR/MCM

FK–t-C4H9CH (CH3)OH –t-C 4 H 9 CH (C2 H5)OH

34.9

146

Derived

1996MIH/GAT

33.8

141

FK–Si(CH3)2F2

55.5

232

ICR

1977MUR/BEA

FK–SiMeF3 –SiMe3F –SiMe4

50.5 38.3 29.9

211 160 125

ICR

1985LAR/MCM

(continued) 7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

1372

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.3 (continued) BDEs of FK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated atom)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

FK–SiMe3R RZOCH2CH3 OCH2CF3 OCH(CH3)2 OSiMe3

31.4G1.2 23.8G1.2 32.1G1.8 21.4G2.1

131.4G4.8 99.6G4.8 134.3G7.5 89.5G8.8

CID

2005KRO/WEN

FK(C5F8)x–(C5F8) xZ0 1

R30 6.7G0.3

R126 28.0G1.3

MS

2005HIR/FUJ

FK–BF2(OCH3)

62

259

ICR

1985LAR/MCM

FK–BF(CH3)2

61.8

259

ICR

1977MUR/BEA

FK–BF(OMe)2 –B(OMe)3 –B(OEt)3

52G5 42G3 44G3

218G21 176G13 184G13

ICR

1985LAR/MCM

FK–BMe3

(1) 58.5 (2) 47.2 (2) 51.0G2

245 198 213G8

ICR

(1) 1977MUR/BEA (2) 1985LAR/MCM

F–BEt3 –BFEt2 –B(iPr)3 –BF(iPr)2

62.0 64.0 65.0 66.5

259 268 272 278

ICR

1977MUR/BEA

FK–Fe(CO)5

40.9G3

171G13

Ion reactions

1985LAN/SAL

FK–F9Mo2

96.1G8.6

402G36

Ion reactions

1984PYA/GOR

–BEt3

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1373

FK–F9U2

124G12

519G50

Ion reactions

1988BOR/BOL

FK–F10U2

129G12

540G50

Ion reactions

1984PYA/GOR

FK–H16B4U

45.0G8.1

188G34

Electronattach.

1984BAB/HER

FK–C6H6

15.3

64

HP MS

1987HIR/MIZ

FK(C6F6)x–C6F6 xZ0 1

27.5 7.5

115 31.4

HP MS

1987HIR/MIZ

FK–C6F5H –C6F5CF3 –C6F5C(O)CF3 –C6F5CN –C6F5NO2

29.2 33.6 37.5 39.3 41.1

122 141 157 164 172

HP MS

1987HIR/MIZ

FK–C6F5CH2OH

32.4

136

Derived

1996MIH/GAT

FK–C6H5OH –C6H5CH2F –C6H5NH2

41.3 24.4 31.2

173 102 131

ICR

1983LAR/MCM

FK–(CH3)2[cycloSi(CH2)3]

37.7G2.2

158G9

Ion reactions

1981SUL/DEP

(1) 58G5 (2) 22.0G0.4 (2) 18.3G1.0

243G21 92.0G1.7 76.6G4.2

(1) ICR (2) Ion reactions

(1) 1985LAR/MCM (2) 1999BOG/PES

FK(C4H10BF)x– C6H10BF xZ0 1 2

(continued)

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

1374

Comprehensive Handbook of Chemical Bond Energies

Table 27.1.3 (continued) BDEs of FK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZ dissociated atom)

kcal/mol

kJ/mol

FK–CH2F(cycloC2H3O) –pyrrole

25.5

107

34.2

143

FK 2 –F

30.0G3

126G13

Methods (reference in parentheses)

References

ICR

1983LAR/MCM

CID

2000ART/NIZ

27.2 Cl–, ClC–, and ClK–X bonds 27.2.1 Cl–X bonds Table 27.2.1 BDEs of Cl–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Cl–Cl

(1) 57.978G0.001 (2) 57.939G0.461

242.580G0.004 242.417G1.930

Spectroscopy

(1) 1979HUB/HER (2) 1997SAM/SAK

Cl2–Cl

1

4

Est. by exp.

1989KAW/SAT

Cl–F

(1) 61.24 (2) 62.34

256.23 260.83

Spectroscopy

(1) 1974NOR (2) 1999ALE/SET

Cl–Br

(1) 52.0G0.1 (2) 52.42G0.01

217.5G0.3 219.32G0.05

Spectroscopy

(1) 1979CLY/MCD (2) 1995TEL

Cl–I

50.5G0.1

211.3G0.4

Spectroscopy

1968GAY

35

50.540G0.001 50.551G0.001

211.459G0.001 211.507G0.001

Spectroscopy

1978KIN/MCF

37

Cl–I Cl–I

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1375

Cl2–He

(1) 0.03, at 0 K (2) 0.15 (3) 0.11

0.11 0.64 0.46

(1) Review (2) Spectroscopy (3) Combined

(1) 1988EVA/CLI (2) 1989CLI/SIV (3) 1993BEN/CAS

HCl–He

0.03, at 0 K

0.12

Spectroscopy

1990lOV/NES

Cl2–Ne

0.16, at 0 K

0.66

Review

1988EVA/CLI

HCl–Ne

w0.09, at 0 K

w0.4

Near IR

1988LOV/NES

ICl–Ne

0.14, at 0 K

0.58

Spectroscopy

1987DRO/LES

Cl2–Ar

0.54, at 0 K

2.25

Spectroscopy

1988EVA/CLI

FCl–Ar

0.66, at 0 K

2.75

Review

1988EVA/CLI

HCl–Ar

(1) (2) (3) (4)

4.6 2.2 1.36 5.4

Spectroscopy

(1) (2) (3) (4)

FCl–Kr

0.83, at 0 K

3.45

Review

1988EVA/CLI

Cl–Xe

(1) 1.6 (2) 1.69 (3) 1.36

6.7 7.08 5.68

(1) Spectroscopy (2) Spectroscopy (3) Scattering

(1) 1979HUB/HER (2) 1983TEL (3) 1992AQU/CAP

HCl–Xe

(1) 1.6, at 0 K (2) 0.9

6.7 4.0

Spectroscopy

(1) 1963RAN/SIT (2) 1982BOO/EIS

Cl–H

(1) (2) (3) (4)

431.62 431.340G0.010 431.328G0.014 431.361G0.013

(1) (2) (3) (4)

(1) (2) (3) (4)

1.1, at 0 K 0.5 0.33 1.3

103.16 103.093G0.002 103.090G0.003 103.099G0.003

Spectroscopy Spectroscopy Spectroscopy TIPPS

1963RAN/SIT 1982BOO/EIS 1985HOW/PIN 1988HUT

1979HUB/HER 1998MAR/HEP 2002MIC/KOR 2003HU/MEL

(continued)

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

1376

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.1 (continued) BDEs of Cl–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) Cl–D

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(1) 104.32 (2) 104.279G0.003 (1) 104.84

436.47 436.303G0.011 438.64

(1) Spectroscopy (2) TIPPS

(1) 1979HUB/HER (2) 2003HU/MEL

Cl2–Cl2

1

4

Est. by exp.

1989KAW/SAT

Cl–BrBr

38.9

163

Derived from DfH0 from ref.

1996NIST

ClH–HF

1.84, at 0 K

7.68

Photofrag.

1995OUD/MIL

HCl–HCl

(1) (2) (3) (4) (5)

9.0 5.16G0.26 5.24 5.25G0.01 5.25

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

HCl–OCO

w1.23, at 0 K

w5.14

IR

1996OUD/OLS

HCl–SO2

3.5, at 0 K

14.6

IR spectra

1959BUR/SMI

Cl–CH3SCH3

w16, at 0 K

w67

Spectroscopy

2004ENA/YAK

HCl–C2H2

2.37, at 0 K

9.93

Photofrag.

1999OUD/MIL

HCl–C2H4

(1) !3.18G0.74, 0 K (2) 1.5–2.1

!13.31G3.10 6.4–8.7

(1) PI (2) IR

(1) 1986WAL/GRO (2) 1997HER/EVE

HCl–C6H6

(1) 4.79G0.12, 0 K (2) 1.8–3.8 (3) 2.90G0.50

20.04G0.50 7.5–15.9 12.13G2.09

(1) PI (2) REMPI (3) Re-cal.

(1) 1985WAL/GRO (2) 1990GOR/GAR (3) 2002MON/DIM(b)

–T

2.14, at 0 K 1.23G0.06 1.25 1.26G0.01 1.26

Spectroscopy IR POSTS Spectroscopy Spectroscopy

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

1963RAN/SIT 1986PIN/HOW 1996NI/SER 2000NI/SER 2004VIS/OUD

BDEs in the Halogenated Molecules, Clusters and Complexes

1377

HCl–CH3OCH3

(1) 7.1G0.8, 0 K (2) 6.7G0.4

29.7G3.3 28.0G1.7

(1) Raman spec. (2) NMR

(1) 1968GOV/CLA (2) 1974GIL/BER

HCl–C2H5OC2H5

4.7G0.7, at 0 K

19.7G2.9

IR

1960INS/DIC

HCl–furan

2.52, at 0 K

10.56

Spectroscopy

1995BET/BET

27.2.2 ClC–X bonds Table 27.2.2 BDEs of ClD–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

ClC–Cl

(1) 92.0 (2) 92.26G0.07

384.8 386.02G0.30

(1) Derived (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

(H2Cl)C–Cl

9.5

39.6

PI

1979TIE/AND

ClC–F

(1) 66G7 (2) 69.4G2.4

276G29 291G10

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

ClC–Ar

(1) 43.5 (2) 40.4

182 169

Derived

(1) 1988BAL/FEN (2) 1989CHA/BAL

ClC–H

(1) 109.5G0.4 (2) 108.25G0.1

458.1G1.7 452.91G0.2

(1) 1974GUR/KAR (2) 1996NIST

(3) 108.206G0.001 (4) 108.208G0.004

452.734G0.006 452.741G0.018

(1) Derived (2) Derived from IP in ref. (3) Spectroscopy (4) TIPPS

109.294G0.004

457.284G0.017

TIPPS

2003HU/MEL

ClC–D

(3) 2002MIC/KOR (4) 2003HU/MEL

(continued)

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

1378

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.2 (continued) BDEs of ClC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

ClC–O

(1) 123G20 (2) 111.8G0.5

515G84 468.0G2.1

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

ClC–S –SCl

152.2 151.3

637 633

MS

1981KAU/VAH

ClC–N

155.4G2.4

650G10

Derived from IP in ref.

1996NIST

HClC–Ar

5.5G0.9

23.2G3.9

UV PI

1997LI/WAN

HClC–HCl

20.1

83.9

PI

1979TIE/AND

ClC–CCl3

106.8G2.3

447G9.6

UV PI

1996LI/RAN

ClC–CH2Cl

123.8

518

UV PI

1996LI/RAN(d)

ClC–CHF2

146.4G1.2

613G4.8

UV PI

1996ZHA/SHE

ClC–C2H3

163.7G1.2

685G4.8

UV PI

1995SHE/QI

HClC–C2H4

K0.3G0.9

K1.3G3.8

Derived

1986WAL/GRO

Cl2C–O2

13.6G1.7

57G7

CID

2005BAI/HAO

7366—CHAPTER 27—5/2/2007—09:54—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1379

27.2.3 ClK–X bonds Table 27.2.3 BDEs of ClL–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

ClK–Cl

(1) 29.1 (2) 30.0G4.6

121.6 125.4G19.3

(1) Derived (2) Derived from EA in ref.

(1) 1979HUB/HER (2) 1996NIST

ClK–F

R36.9G9.2

R154G39

GIB MS

2001ANG/ERV

ClK–I

23.2G2.4

97G10

Derived

2004ANG/ERV

ClK–Li –Na –K –Rb –Cs

41.2G0.5 31.8G2.3 33.6G2.3 31.3G2.3 32.5G2.3

172.4G1.9 133.1G9.6 140.6G9.6 131.0G9.6 136.0G9.6

PES

1986MIL/LEO

ClK–Mg

29.3G2.3

122.6G9.6

PES

1988MIL/LIN

ClK–Cr

32.3G5

135G21

Derived from EA in ref.

1996NIST

ClK–Ag

(1) 125.0G1.1 (2) 121.9

523.2G4.8 510

PES

(1) 1999LEN/YOU (2) 2000DIS/BOE

ClK–Pb

(1) 12 (2) 12G12

50 49G50

(1) Derived (2) Derived from EA in ref.

(1) 1974GUR/KAR (2) 1996NIST

ClK–Kr

2.2G0.1

9.2G0.4

Electron spectra

2002YOU/LEN

ClK–Xe

3.1

13.0

MS

1980THA/EIS

(continued)

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

1380

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.3 (continued) BDEs of ClK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

ClK–O

(1) 33.4G0.2 (2) 33.4G1.6

139.7G0.8 139.7G6.7

(1) Derived (2) PES

(1) 1992GIL/POL (2) 2000DIS/BOE

ClK–As

53.7G2.5

224.7G10.5

Derived from EA in ref.

1996NIST

35

1.40, at 0 K 1.43 1.60

5.84 5.97 6.69

IR

2001WIL/WEI

ClK–O2

138.6

580

PES

2000DIS/BOE

ClK–Cl2

23.7G1.2

99G5

CID

1998NIZ/POM

ClK–HF

(1) 14 (1) 21.8

59 91.2

(1) Derived (2) ICR

(1) 1971YAM/KEB (2) 1984LAR/MCM

(1) (2) (3) (4) (1) (3) (1) (1)

99.2G0.8 96.7 99.6 123.8G4.2 63.6G0.8 58.6 49.0G1.3 43.1G2.9

(1) (2) (3) (4)

(1) (2) (3) (4)

ClK–H2(ortho) –D2(para) –D2(ortho)

ClK(HCl)x–HCl xZ0

1 2 3

23.7G0.2 23.1 23.8 29.6G1.0 15.2G0.2 14.0 11.7G0.3 10.3G0.7

HP MS ICR HP MS PES

1974YAM/KEB 1984LAR/MCM 1985CAL/KEB 1988MET/KIT

ClK(H2O)(HCl)x–HCl xZ0 1

16.0 12.3

66.9 51.5

Review

1986KEE/CAS

ClK(H2O)2–HCl

13.0

54.4

Review

1986KEE/CAS

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1381

ClK–CF –CCl

21.9G1.1 33.4G2.3

91.6G4.6 139.7G9.6

CID

1999JES/SQU

ClK–CH

(1) 38.3G2.0 (2) 37.7G2.3

160.2G8.4 157.7G9.6

(1) PES (2) CID

(1) 1992GIL/ERV (2) 1999JES/SQU

ClK–CO

O5.0

O21

ICR

1976KAR/KLE

ClK(NO)x–NO xZ0 1

4.1 6.4

17.2 26.8

HP MS

2000HIR/IIN

ClK–SmCl2

61.5G0.5

257.3G2.1

MS

1998KHA/POG

ClK–EuCl2

117.6G7.9

492G33

MS

1993KUD/BUR

ClK–YbCl2

O56.4

O236

MS

1997KUZ/KUD

ClK(NdCl2)x–NdCl2 xZ0 1

65.5G3.6 88.2G5.3

274G15 369G22

MS

1993KUD/POG

ClK–CH2

(1) 28.1G3.2 (2) 23.1G2.9 (3) R27.7G2.3

117.6G13.4 96.7G12.1 R116G10

(1) FT-ICR (2) CID (3) GIB MS

(1) 1985ING/NIB (2) 1997POU/NAS (3) 2001ANG/ERV

ClK–CHF

22.7G2.2

95.0G9.2

CID

1997POU/PAU

ClK–CHCl

(1) 37.0G2.7 (2) 36.5G3.0

154.8G11.3 152.7G12.6

(1) CID (2) FT-ICR

(1) 1997POU/PAU (2) 2000BOR/ING

ClK–CCl2

30.8G2.7

128.9G11.3

CID

1997PAU/SQU

(continued)

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

1382

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.3 (continued) BDEs of ClK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) ClK(HCN)x–HCN xZ0 1 2 3 4 5 6 7 8 N

ClK(CO2)x–CO2 xZ0

1 2 3 N

ClK(N2O)x–N2O xZ0 1 2 3 4 N

ClK(SO2)x–SO2 xZ0

1 2 3 N

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(1) (2) (2) (2) (2) (2) (2) (2) (2) (2) (3)

21.0 21.9 17.9 13.6 11.2 8.8 8.7 7.9 8.2 7.5 w6

87.9 91.6 74.9 56.9 46.9 36.8 36.4 33.1 34.3 31.4 w25

(1) ICR (2) HP MS

(1) 1984LAR/MCM (2) 1988MEO/CYB

(3) Extrapolate

(3) This volume

(1) (2) (3) (2) (2) (2) (4)

8.0 7.6 6.8G0.5 7.2 6.8 w6.4 w5.7

33.5 31.8 28.5G2.1 30.1 28.5 w27 w24

(1) HP MS (2) HP MS (3) PD

(1) 1980KEE/LEE (2) 1986HIR/SHO (3) 1995ARN/BRA

(4) Extrapolate

(4) This volume

(1) (1) (1) (1) (1) (2)

5.79G0.3 5.63G0.3 5.13G0.3 4.85G0.3 4.8G0.3 w4

24.2G1.3 23.6G1.3 21.5G1.3 20.3G1.3 20.1G1.3 w17

(1) HP MS

(1) 1993HIR/ARU

(2) Extrapolate

(2) This volume

(1) (2) (3) (4) (1) (4) (1) (1) (5)

21.8 22.1 20.9 22.2 12.3 12.3 10.0 8.6 w5.7

91.2 92.4 87.4 92.9 51.5 51.5 41.8 36.0 w24

(1) (2) (3) (4)

(1) (2) (3) (4)

HP MS FA ICR HP MS

(5) Extrapolate

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

1980KEE/LEE 1984BOH/FAH 1985LAR/MCM 1985CAL/KEB

(5) This volume

BDEs in the Halogenated Molecules, Clusters and Complexes

1383

ClK(H2O)x–SO2 xZ1 2

17.4 14.1

72.8 59

HP MS

1984UPS/SCH

ClK(H2O)(SO2)–SO2

11.8

49.4

HP MS

1984UPS/SCH

ClK–SCl2

20.3G2

85G8

CID

2000GAI/POM

ClK–SeCl2 –TeCl2

31.8G2.2 40.6G1.7

133G9 170G7

CID

2003LOB/HAO

(1) (2) (2) (2) (2) (3)

11.7 8.77G0.2 7.84G0.2 7.18G0.2 w6.8 w6.4

49 36.7G0.8 32.8G0.8 30.0G0.8 w29 w27

(1) ICR (2) HP MS

(1) 1985LAR/MCM (2) 1993HIR/FUJ

(3) Extrapolate

(3) This volume

(1) (1) (1) (1) (1) (2)

10.8G0.3 7.3G0.3 6.8G0.3 6.6G0.3 w6.5 w4.4

45.2G1.3 30.5G1.3 28.5G1.3 27.6G1.3 w27 w19

(1) HP MS

(1) 2004HIR/FUJ

(2) Extrapolate

(2) This volume

(1) (2) (3) (4) (5) (1) (2) (5) (6) (7) (1) (2) (5) (6) (7)

13.1 14.9G0.2 14.8 14.4 14.7G0.6 12.7 12.6G0.1 13.0G0.4 13.8 11.9 11.7 11.5G0.3 11.8G0.3 12.2 9.5G0.5

54.8 62.3G0.8 62 60.2 61.5G2.5 53.1 52.7G0.4 54.4G1.7 57.9 49.8 49.0 48.1G1.3 49.4G1.3 51.1 39.7G2.1

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

ClK(CS2)x–CS2 xZ0 1 2 3 N

ClK(SCO)x–SCO xZ0 1 2 3 4 N

ClK(H2O)x–H2O xZ0

1

2

HP MS HP MS MS ICR HP MS

(6) PES (7) HP MS

1970ARS/YAM 1980KEE/CAS 1982BUR/HAY 1984LAR/MCM 1988HIR/MIZ

(6) 1994MAR/POL (7) 1995DUN/MCM

(continued)

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

1384

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.3 (continued) BDEs of ClK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) 3

4 5 6 N

kcal/mol (1) (2) (5) (6) (5) (6) (5) (6) (5) (6) (8)

11.7 10.9G0.7 10.6G0.3 9.7 9.5G0.3 6.7 8.8G0.4 8.5 w8.1 6.9 w10.5

kJ/mol 49.0 45.6G2.9 44.4G1.3 40.6 39.7G1.3 28 36.8G1.7 35.7 w34 28.9 w44

Methods (reference in parentheses)

References

(8) Extrapolate

(8) This volume

ClK(CH3OH)(H2O)x–H2O xZ0 1

10.9G0.2 10.4G0.2

45.6G0.8 43.5G0.8

HP MS

1991EVA/KEE

ClK(CH3OH)2–H2O

7.7G0.7

32.2

HP MS

1991EVA/KEE

ClK(HCl)2–H2O

7.6

31.8

HP MS

1986KEE/CAS

ClK(HCl)(H2O)x–H2O xZ0 1

10.5 9.6

43.9 40.2

HP MS

1986KEE/CAS

ClK(SO2)(H2O)x–H2O xZ0 1

10.4 9.3

43.5 38.9

HP MS

1984UPS/SCH

ClK(SO2)2–H2O

9.9

41.4

HP MS

1984UPS/SCH

ClK–D2O

14.7G0.2

61.5G0.8

ICR

1988LAR/MCM

ClK–H2S

21

87.9

ICR

1988LAR/MCM

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1385

ClK–NH3

(1) 10.5 (2) 8.2

43.9 34.3

(1) ICR (2) HP MS

(1) 1984LAR/MCM (2) 1987EVA/KEE

ClK–BF3 –PF3 –AsF3

26.0 15.5 25.8

109 64.9 108

ICR

1985LAR/MCM

ClK–PF2Cl

23.7G2.2

99G9

CID

2003CHE/LOB

ClK–BCl3

69.0G2.0

288.7G8.4

MS

1977KRI/TIT

ClK–PCl3 –AsCl3 –SbCl3 –BiCl3

21.5G1.7 27.5G1.7 38.2G2 36.6G3.6

90G7 115G7 160G8 153G15

CID

2002WAL/CHE

ClK–AlCl3 –AlFCl2 –AlF2Cl –AlF3

76.7G2.9 75.3G2.9 74.3G2.9 74.3G2.9

32G12 315G12 311G12 311G12

MS

1992PER/KOR

ClK(LaCl3)x–LaCl3 xZ0 1

68.6G3.6 32.4G3.5

287G15 136G15

MS

1987BUT/KUD

ClK(NdCl3)x–NdCl3 xZ0 1

69.1G3.8 55.0G2.2

289G16 230G9

MS

1998KHA/POG

ClK–SmCl3

69.1G3.8

289G16

MS

1998KHA/POG

ClK(EuCl3)–EuCl3

114G11

477G46

MS

1993KUD/BUR

ClK(TbCl3)x–TbCl3 xZ1 2

72.7G1.6 89.4G2.5

304.2G6.7 374.0G10.5

MS

1999KHA/KUD

(continued)

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

1386

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.3 (continued) BDEs of ClK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) 3 4 5

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

93.3G2.3 87G12 76G20

390.4G9.6 364G42 318G84

ClK(ErCl3)x–ErCl3 xZ0 1 2

78.1G3.9 78G15 93G15

327G16 326G63 389G63

MS

2002POG/MOT

ClK–YbCl3

74.3G7.2

311G30

MS

1997KUZ/KUD

ClK(LuCl3)x–LuCl3 xZ0 1 2 3 4 5

71.0G3.6 49.5G2.4 57.8G7.6 75.3G5.3 45G19 95G23

297G15 207G10 242G32 315G22 188G79 397G96

MS

1997POG/KUD

ClK–H2O2

22.1

92.4

FA

1984BOH/FAH

ClK–OaSF2

17.1

71.5

ICR

1985LAR/MCM

ClK–OaSCl2

20.4G1.8

85.4G7.6

CID

2001BAC/HAY

ClK–OaSeCl2

35.9G2.4

150G10

CID

2003LOB/HAO

ClK–C(O)F2 –C(O)Cl2

12.5 12.5

52.3 52.3

ICR

1985LAR/MCM

ClK–OaPF3

13.9

58.2

ICR

1985LAR/MCM

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1387

ClK–OaPCl3 –SaPCl3

10.3G1.2 9.8G1

43G5 41G4

CID

2003CHE/LOB

ClK–SiF4

23.4

97.9

ICR

1985LAR/MCM

ClK–SiCl4

(1) 24.2 (2) 25.1G2

101 105G8

(1) ICR (2) CID

(1) 1985LAR/MCM (2) 2005HAO/KAS

ClK–GeCl4 –SnCl4

33.7G1.4 56.2G2

141G6 235G8

CID

2005HAO/KAS

ClK–ThCl4

24.2

101

ICR

1985LAR/MCM

ClK(CH4)x–CH4 xZ0 1

3.8G0.2 3.5G0.2

15.9G0.8 14.6G0.8

HP MS

2001HIR/MIZ

ClK–CHF3 –CH3F –CHF2Cl –CHFCl2

16.7 11.5 17.2 17.6

69.9 48.1 72.0 73.6

ICR

1984LAR/MCM

ClK–CBrF3 –CIF3

16.5G0.2 23.6G0.2

69.0G0.8 98.7G0.8

HP MS

2006BOG/MCM

(1) (2) (3) (4) (4) (4) (4) (4) (4) (4) (4) (5)

63.6 51.0 43.5G4.2 49.0G0.8 46.4G0.8 35.1G0.8 31.8G0.8 25.9G0.8 24.3G0.8 20.1G0.8 19.7G0.8 w20

(1) (2) (3) (4)

(1) (2) (3) (4)

ClK(CH3Cl)x–CH3Cl xZ0

1 2 3 4 5 6 7 N

15.2 12.2 10.4G1.0 11.7G0.2 11.1G0.2 8.4G0.2 7.6G0.2 6.2G0.2 5.8G0.2 4.8G0.2 4.7G0.2 w4.8

HP MS ICR HP MS HP MS

(5) Extrapolate

1972YAM/KEB 1984LAR/MCM 1996LI/ROS 2001HIR/MIZ

(5) This volume

(continued)

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

1388

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.3 (continued) BDEs of ClK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) ClK(CH2Cl2)x–CH2Cl2 xZ0

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

(1) (2) (3) (3) (3) (3) (3) (4)

15.5 15.8 14.8G0.2 13.1G0.2 9.7G0.2 9.0G0.2 7.7G0.2 w6.6

64.9 66.1 61.9G0.8 54.8G0.8 40.6G0.8 37.7G0.8 32.2G0.8 w28

(1) HP MS (2) ICR (3) HP MS

(1) 1974DOU/DAL (2) 1984LAR/MCM (3) 2001HIR/MIZ

(4) Extrapolate

(4) This volume

(1) (2) (3) (4) (5) (5) (5) (6)

15.2 19.1 18.1 18.1 19.5G0.2 14.7G0.2 11.8G0.2 w7.2

63.6 79.9 75.7 75.7 81.6G0.8 61.5G0.8 49.4G0.8 w30

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

(6) Extrapolate

(6) This volume

13.4G0.2 9.3G0.2

56.1G0.8 38.9G0.8

HP MS

2001HIR/MIZ

ClK–CH3Br

(1) 10.9 (2) 12.5G1.0

45.6 52.3G4.2

HP MS

(1) 1974ROB/ROB (2) 1996LI/ROS

ClK–CH3I

9.8

41.0

HP MS

1974DOU/ROB

56.1 60.2G0.8 66.1 56.9 70.3G1.7 51.0 52.3 50.2G2.9

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

1 2 3 4 N

ClK(CHCl3)x–CHCl3 xZ0

1 2 N

ClK(CCl4)x–CCl4 xZ0 1

ClK(CH3CN)x–CH3CN xZ0

1

(1) (2) (3) (4) (5) (1) (4) (5)

13.4 14.4G0.2 15.8 13.6 16.8G0.4 12.2 12.5 12.0G0.7

HP MS HP MS ICR KIM MS HP MS

HP MS HP MS ICR Review Derived

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

1971YAM/KEB 1974DOU/DAL 1984LAR/MCM 1993GIL/GRI 2001HIR/MIZ

1972YAM/KEB 1985SIE 1984LAR/MCM 1994HIR/YAM 1996MAR/PER

BDEs in the Halogenated Molecules, Clusters and Complexes

2

3

4 5 6 7 8 9 10 11 12 13 N

(1) (4) (5) (1) (4) (5) (4) (5) (4) (5) (4) (5) (4) (5) (5) (5) (5) (5) (5) (5) (6)

10.6 11.2 12.0G0.7 6.2 10.9 9.0G0.8 9.8 5.8G0.9 9.5 5.8G1 9.4 3.9G1.1 w9.2 2.8G1.2 4.4G1.4 2.1G1.5 1.8G1.6 K0.5G1.7 0.9G1.8 K0.5G1.9 w7.9

1389

44.4 46.9 50.2G2.9 25.9 45.6 37.7G3.3 41.0 24.3G3.8 39.7 24.3G4.2 39.3 16.3G4.6 w39 11.7G5.0 18.4G5.9 8.8G6.3 7.5G6.7 K2.1G7.1 2.4G7.5 K2.1G7.5 w33

(6) Extrapolate

(6) This volume

ClK(iso-PrCl)–CH3CN

11.7

49.0

HP MS

2006BOG/MCM

ClK(iso-PrBr)–CH3CN

13.9

58.2

HP MS

2006BOG/MCM

(1) (2) (3) (4) (5) (2) (3) (5) (6) (2) (3) (5) (6) (2) (6) (2) (6) (2) (2) (2) (2)

70.3 72.8 71.5G0.4 78.2G2.1 73.2G1.3 59.0 57.3G0.8 59.0G1.7 54.4 49.4 45.2G1.3 48.1G0.8 51.5 43.9 46.9 38.5 43.9 37.2 33.5 31.8 31.8

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

ClK(CH3OH)x–CH3OH xZ0

1

2

3 4 5 6 7 8

16.8 17.4 17.1G0.1 18.7G0.5 17.5G0.3 14.1 13.7G0.2 14.1G0.4 13.0 11.8 10.8G0.3 11.5G0.2 12.3 10.5 11.2 9.2 10.5 8.9 8.0 7.6 7.6

ICR HP MS HP MS Photodetach. HP MS

(6) HP MS

1984LAR/MCM 1987HIR/MIZ 1991EVE/KEE 1997YAN/LIN 1999BOG/PES

(6) 1973YAM/PAY

(continued)

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

1390

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.3 (continued) BDEs of ClK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) 9 10 N

kcal/mol

Methods (reference in parentheses)

kJ/mol

(2) 7.4 (2) 7.3 (7) w8.7

31.0 30.5 w37

ClK(CH3OH)(H2O)x– CH3OH xZ0 1

13.2G0.1 10.8G0.8

ClK(H2O)2–CH3OH

References

(7) Extrapolate

(7) This volume

55.2G0.4 45.2G3.3

HP MS

1991EVA/KEE

11.4G0.3

47.7G1.3

HP MS

1991EVA/KEE

ClK(iso-PrCl)–CH3OH

14.6

61.1

HP MS

2006BOG/MCM

ClK(iso-PrBr)–CH3OH

14.8

61.9

HP MS

2006BOG/MCM

ClK–CH3SH

15.5G3.0

64.9G13.8

FT-ICR

1995STA/GRO

(1) (2) (3) (4) (4) (5) (5) (3) (5) (3) (5) (6)

37.2 27.4 25.6 27.7G2.2 11.2G2.2 34.1G3.1 22.2G2.7 14.1 14.1G2.2 10.1 10.1G2.0 w11

155.6 114.6 107.1 116G9 47G9 142.7G13 92.9G11.3 59.0 59.0G9.2

(1) (2) (3) (4)

(1) (2) (3) (4)

(1) (2) (1) (2)

16.7G0.1 15.6G0.6 13.1 13.0G0.5

69.9G0.4 65.3G2.5 54.8 54.4G2.1

ClK(HC(O)OH)x– HC(O)OH xZ0

1 2 3 4 N

ClK(CH3NO2)x–CH3NO2 xZ0 1

42.3G8.4 w46

HP MS HP MS ICR CID

1971YAM/KEB 1982FRE/IKU 1984LAR/MCM 1999WAL/SUN

(5) HP MS

(5) 1978LUC/WLO

(6) Extrapolate

(6) This volume

HP MS

(1) 1985SIE (2) 2003WIN

7366—CHAPTER 27—5/2/2007—09:56—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

2 3 N

1391

(2) 11.1G0.5 (2) 9.6G1 (3) w8.6

46.4G2.1 40.2G4 w36

(3) Extrapolate

(3) This volume

ClK–2CH3NO2

13.1G0.1

54.8G0.4

HP MS

1985SIE

ClK(C2H4)x–C2H4 xZ0 1 2 3 4 5 6 N

(1) (1) (1) (1) (1) (1) (1) (2)

22.6G1.3 22.2G1.3 20.5G1.3 20.5G1.3 18.4G1.3 18.0G1.3 17.6G1.3 w14

(1) HP MS

(1) 2001HIR/KAT

(2) Extrapolate

(2) This volume

ClK–HCCN

43.7G2.5

183G10.5

CID

2002POU/UPS

ClK–CF3CF2H –CF2HCH2F –CF3CHF2

18.8 w18.9 18.8

78.7 w79 78.7

ICR

1984LAR/MCM

ClK–CH3CHF2

(1) 14.9 (2) 12.8

62.3 53.6

(1) ICR (2) HP MS

(1) 1984LAR/MCM (2) 2005BOG/MCM

ClK(iso-PrCl)–CH3CHF2

10.9

45.6

HP MS

2006BOG/MCM

ClK(iso-PrBr)–CH3CHF2

12.4

51.9

HP MS

2006BOG/MCM

ClK–CH3CH2Cl

(1) 14.5G4.5 (2) 12.4G1.0 (2) 13.6G1.0

61G119 51.9G4.2 56.9G4.2

(1) ICR (2) HP MS

(1) 1973RIV/BRE (2) 1996LI/ROS

(1) (2) (3) (2) (3)

72.4 73.6 74.9G1.7 67.4 64.0G0.8

(1) ICR (2) HP MS (3) HP MS

(1) 1984LAR/MCM (2) 1987HIR/MIZ (3) 1999BOG/PES

–CH3CH2Br

ClK(C2H5OH)x–C2H5OH xZ0

1

5.4G0.3 5.3G0.3 4.9G0.3 4.9G0.3 4.4G0.3 4.3G0.3 4.2G0.3 w3.2

17.3 17.6 17.9G0.4 16.1 15.3G0.2

(continued)

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

1392

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.3 (continued) BDEs of ClK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) 2 3 4 5 6 7 8 9 N

kcal/mol (2) (3) (2) (2) (2) (2) (2) (2) (2) (4)

12.8 13.9G0.7 12.0 11.5 11.1 9.8 9.2 9.0 w8.9 w9.7

kJ/mol 53.6 58.2G2.9 50.2 48.1 46.4 41.0 38.5 37.7 w37 w40

Methods (reference in parentheses)

References

(4) Extrapolate

(4) This volume

100 86 100 90

ICR

1984LAR/MCM

ClK–OHCH2CH2OH 25.3G1.0 –OHCH2CH2CH2OH 28.3G1.7 –OHCH2CH2CH2CH2OH 30.2G1.7

105.9G4.2 118.4G7.1 126.4G7.1

HP MS

1995ZHA/BEG

ClK–CH3OCH3 –CHF2OCF3

7.5G0.2 17.5G0.2

31.4G0.8 73.2G0.8

HP MS

2001BOG/LEE

ClK(CH3OCF3)x–CH3OCF3 xZ0 1

13.6G0.2 12.7G0.2

56.9G0.8 53.1G0.8

HP MS

2001BOG/LEE

ClK(CHF2OCHF2)x– CHF2OCHF2 xZ0 1

28.2G0.2 21.4G0.2

118.0G0.8 89.5G0.8

HP MS

2001BOG/LEE

ClK–CH3C(O)H

14.4

60.2

ICR

1984LAR/MCM

ClK–CF3C(O)F –CF3C(O)Cl

16.7 17.8

69.9 74.5

ICR

1985LAR/MCM

ClK–CF3CH2OH –CH2FCH2OH –CHF2CH2OH –CH2ClCH2OH

24.0 20.5 24.0 21.5

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1393

ClK–CH3C(O)OH

(1) 21.6 (2) 23.9 (3) 24.4G0.2

90.4 100.0 102.1G0.8

(1) HP MS (2) ICR (3) HP MS

(1) 1971YAM/KEB (2) 1984LAR/MCM (3) 1985SIE

ClK–CH3OCOCl

14.1

59.0

ICR

1985LAR/MCM

ClK((CH3)2SO)x–(CH3)2SO xZ0 1 2 3 4 N

(1) (2) (2) (2) (2) (3)

77.8 66.9 62.3 61.1 57.7 w43

(1) HP MS (2) HP MS

(1) 1984MAG/CAL (2) 1985SIE

(3) Extrapolate

(3) This volume

ClK–CF3CH2NH2

w18.0

w75.3

ICR

1984LAR/MCM

ClK(C3F6)x–C3F6 xZ0 1 2

12.6G0.3 9.6G0.3 8.9G0.3

52.7G1.3 40.2G1.3 37.2G1.3

HP MS

2002HIR/TAK

ClK(C3H6)x–C3H6 xZ0 1 2 3 4 5 6 N

(1) (1) (1) (1) (1) (1) (1) (2)

24.7G1.3 24.3G1.3 21.8G1.3 19.2G1.3 18.8G1.3 18.4G1.3 18.0G1.3 w17

(1) HP MS

(1) 2001HIR/KAT

(2) Extrapolate

(2) This volume

ClK–CH3CH2CH2Br

14.2G1.0

59.4G4.2

HP MS

1996LI/ROS

ClK–(CH3)2CHCl

14.7G1.0

61.5G4.2

HP MS

1996LI/ROS

ClK(M)–(CH3)2CHCl MZCH3OH CH3CN CH3CHF2 CH3C(O)CH3

11.0 11.0 11.3 11.7

46.0 46.0 47.3 49.0

HP MS

2005BOG/MCM

18.6 16.0 14.9 14.6 13.8 w10.3

5.9G0.3 5.8G0.3 5.2G0.3 4.6G0.3 4.5G0.3 4.4G0.3 4.3G0.3 w4

(continued)

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

1394

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.3 (continued) BDEs of ClK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

ClK–(CH3)2CHBr

15.2G1.0

63.6G4.2

HP MS

1996LI/ROS

ClK(M)–(CH3)2CHBr MZCH3OH CH3CN CH3CHF2 CH3C(O)CH3

11.8 12.3 11.9 11.9

49.4 51.5 49.8 49.8

HP MS

2005BOG/MCM

(1) (2) (2) (2) (2) (2) (2) (2) (2) (3)

17.7 20.4 15.8 14.2 13.3 12.6 11.6 11.0 w10.8 10.6

74.1 85.4 66.1 59.4 55.6 52.7 48.5 46.0 w45 w44

(1) ICR (2) HP MS

(1) 1984LAR/MCM (2) 1994HIR/YAM

(3) Extrapolate

(3) This volume

17.6 18.3 19.4G0.2 15.6 16.7G0.3 12.5 14.9G0.5 11.9 11.6 11.3 11.1 w10.9 w10.2

73.6 76.6 81.2G0.8 65.3 69.9G1.3 52.3 62.3G2.1 49.8 48.5 47.3 46.4 w46 w42

(1) ICR (2) HP MS (3) HP MS

(1) 1984LAR/MCM (2) 1987HIR/MIZ (3) 1999BOG/PES

(4) Extrapolate

(4) This volume

w99 O111

ICR

1984LAR/MCM

ClK(n-C3H7OH)x–nC3H7OH xZ0 1 2 3 4 5 6 7 N

ClK(i-C3H7OH)x–i-C3H7OH xZ0 (1) (2) (3) 1 (2) (3) 2 (2) (3) 3 (2) 4 (2) 5 (2) 6 (2) 7 (2) N (4)

ClK–(CH2F)2CHOH –(CF3)2CHOH

w23.6 O26.5

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

ClK(MeC(O)Me)x– MeC(O)Me xZ0

1 2

(1) (2) (3) (4) (3) (3)

13.7 14.1 12.4 14.1 11.5 w10.4

57.3 59.0 51.9 59.0 48.1 w43.5

(1) (2) (3) (4)

HP MS ICR Review HP MS

1395

(1) (2) (3) (4)

1982FRE/IKU 1984LAR/MCM 1994HIR/YAM 2002BOG/MCM

ClK(iso-PrCl)–MeC(O)Me

10.5

43.9

HP MS

2006BOG/MCM

ClK(iso-PrBr)–MeC(O)Me

11.9

49.8

HP MS

2006BOG/MCM

ClK–CH3C(O)CH2F –CH3C(O)CF3 –CF3C(O)CHF2

(1) (1) (1) (2) (1) (3)

77 57.3 109.2 97.9 120.5 95.8

(1) HP MS

(1) 2002BOG/MCM

(2) ICR

(2) 1984LAR/MCM

(3) ICR

(3) 1985LAR/MCM

–CF3C(O)CF3

18.4 13.7 26.1 23.4 28.8 22.9

ClK–(CH2F)2HC(O)H

23.6

98.7

ICR

1984LAR/MCM

ClK–(CH3)3CF –(CH3)3CCl

(1) (1) (2) (2)

55.6 59.8 69.5G4.2 74.1G4.2

(1) ICR

(1) 1984LAR/MCM

(2) HP MS

(2) 1996LI/ROS

–(CH3)3CBr

13.3 14.3 16.6G1.0 17.7G1.0

ClK–Si(CH3)3Cl –Ge(CH3)3Cl –Sn(CH3)3Cl

14.3G1.4 22.2G1.4 31.3G1.7

60G6 93G6 131G7

CID

2005HAO/KAS

ClK–n-C4H9OH

17.6G2.0

73.6

ICR

1984LAR/MCM

(1) (2) (3) (4) (5)

80.3 75.7 81.6 82.8 84.5G1.7

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

ClK(t-C4H9OH)x–tC4H9OH xZ0

19.2 18.1 19.5 19.8 20.2G0.4

HP MS ICR HP MS HP MS HP MS

1977KEB 1984LAR/MCM 1985SIE 1987HIR/MIZ 1999BOG/PES

(continued)

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

1396

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.3 (continued) BDEs of ClK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) 1 2 3 4 5 N

kcal/mol (4) (5) (4) (5) (4) (4) (4) (6)

14.9 16.9G0.2 13.7 15.8G0.3 12.7 11.9 w11.4 w10.8

kJ/mol

Methods (reference in parentheses)

References

62.3 70.7G0.8 57.3 66.1G1.3 53.1 49.8 w48 w45

(6) Extrapolate

(6) This volume

HP MS

1995ZHA/BEG

ClK–OHCH2Cb CCH2OH(trans) –OHCH2Ca CCH2OH(cis)

28.9G1.1

120.9G4.6

32.9G1.5

137.7G6.2

ClK–CH3C(O)C2H5 –(CF3)2CH3C(O)H –(CH3)3CC(O)H

14.8 O26.5 15.0

61.9 O111 62.8

ICR

1984LAR/MCM

ClK–B(C2H5)3

23.8G2.0

99.6G8.4

ICR

1984LAR/MCM(c)

ClK–t-C4H9CN

18.5G1.0

77.4G4.2

HP MS

1996LI/ROS

ClK–C2H5OC2H5

9.0G0.2

37.7G0.8

HP MS

2001BOG/LEE

ClK–C2H5C(O)C2H5

14.1

59.0

ICR

1984LAR/MCM

ClK(C5F8)x–(C5F8) xZ0 1

13.8G0.2 11.0G0.2

57.7G0.8 46.0G0.8

MS

2005HIR/FUJ

ClK–cyclo-C5H10 –cyclo-C5H10

7.4G0.2 7.9G0.2

31.0G0.8 33.1G0.8

HP MS

2001MCM

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1397

ClK–cyclo-C6H12 –cyclo-C6H14

8.1G0.2 9.5G0.2

33.9G0.8 39.7G0.8

HP MS

2001MCM

ClK–cyclo-C7H14 –cyclo-C7H16

10.4G0.2 10.3G0.2

43.5G0.8 43.1G0.8

HP MS

2001MCM

ClK–cyclo-C8H16 –cyclo-C8H18

10.6G0.2 11.0G0.2

44.4G0.8 46.0G0.8

HP MS

2001MCM

ClK–DMNB 22.0G0.7 –DNB 26.1 –DMDNP 22.9 DMNBZ2,3-dimethyl-2,3dinitrobutane DNBZ1,4-dinitrobutane DMDNPZ2,3-dimethyl-2,4dinitropentane

92.1G3.1 109 96

IMS

2001LAW/NEU

29.4 19.8

123 82.8

HP MS

1988MEO(c)

ClK–cyclo-C6H4

(1) 15.7G3.0 (2) 16.7G3.7 (3) 17.5G3.9

65.7G12.6 69.9G15.5 73.2G16.3

(1) CID (2) CID (3) FT-ICR

(1) 1991WEN/PAU (2) 1995WEN/SQU(b) (3) AND/RIV

ClK–C6H6

(1) (2) (3) (4)

43.5 41.4 39.3 36.4

(1) (2) (3) (4)

(1) (2) (3) (4)

ClK–methyl, 1,2phenylenebis

20.1G1.6

84.1G6.7

CID

2000HAM/WEN

ClK–C6H5Cl

(1) 13.6 (2) 12.0G0.1 (3) 12.6

56.9 50.2G0.4 52.7

(1) ICR (2) HP MS (3) HP MS

(1) 1984LAR/MCM (2) 1985SIE (3) 1991PAU/KEB

(Cl)K(AcAlaNH)x– AcAlaNH xZ0 1 AcZCH3CO AlaZNHCH(CH3)CO

10.4 9.9 9.4 8.7

HP MS ICR HP MS HP MS

1981SUN/NIS 1984LAR/MCM 1988HIR/MIZ 1991PAU/KEB

(continued)

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

1398

Comprehensive Handbook of Chemical Bond Energies

Table 27.2.3 (continued) BDEs of ClK–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

ClK–C6H5OH

(1) (2) (3) (4)

ClK–C6H5CN

References

81.2 114.6 104.6 110.9

HP MS

(1) (2) (3) (4)

16.0

66.9

HP MS

1991PAU/KEB

ClK–o-C6H4F2 –m-C6H4F2 –p-C6H4F2

14.3 14.6 13.8

59.8 61.1 57.7

ICR

1984LAR/MCM

ClK–1,2-C6H4F2 –1,3-C6H4F2 –1,4-C6H4F2

14.3G2 14.6G2 13.8G2

59.8G8 61.1G8 57.7G8

ICR

1984LAR/MCM

(1) 16.8G1.0 (2) 15.5G1.0 (2) 13.8

70.3G4.2 64.9G4.2 57.7

HP MS

(1) 1986CHO/KEB (2) 1987HIR/MIZ

(1) (2) (3) (1) (2) (3) (1) (2) (3) (1) (2) (3)

116.7G8.4 112.5 119.7 123.8G8.4 120.9 125.9 146.9G8.4 140.6 147.7 107.1G8.4 102.9 108.4

HP MS

(1) 1977CUM/FRE (2) 1982FRE/IKU (3) 1990PAU/KEB

84.1G6.7 164.0G7.5

CID

2000HAM/WEN

ClK(C6F6)x–C6F6 xZ0 1

ClK–4-F–C6H4OH

–4-Cl–C6H4OH

–4-CN–C6H4OH

–4-CH3–C6H4OH

ClK–3-CH2C6H4CD2 –3-CH3C6H4CD2

19.4 27.4 25.0 26.5

kJ/mol

Methods (reference in parentheses)

27.9G2.0 26.9 28.6 29.6G2.0 28.9 30.1 35.1G2.0 33.6 35.3 25.6G2.0 24.6 25.9

20.1G1.6 39.2G1.8

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

1971YAM/KEB 1977KEB 1982FRE/IKU 1990PAU/KEB

BDEs in the Halogenated Molecules, Clusters and Complexes

1399

ClK–C6H5NO2

(1) 16.3G1.0 (2) 16.5

68.2G4.2 69.0

HP MS

(1) 1986CHO/KEB (2) 1991PAU/KEB

ClK–C6HF4NO2 –4-CN–C6H4NO2 –3-CF3–C6H4NO2 –C6F5CN –3-F–C6H4NO2

27.0 20.0 19.5 19.9 18.7

113.0 83.7 81.6 83.3 78.2

HP MS

1986CHO/KEB

ClK(C5H5N)x–C5H5N xZ0 1

12.7 11.7

53.1 49.0

HP MS

1988HIR/MIZ

ClK–p-benzoquinone, 2,3,5,6-tetrafluoro

27.0G1.0

113.0G4.2

HP MS

1986CHO/KEB

ClK–pyrrole

18.8G2.0

78.7G8.2

ICR

1984LAR/MCM

ClK–Fe(CO)5

13.9G3.0

58.2G12.6

Ion reactions

1985LAN/SAL

38.0G1.2

159.2G4.8

ES/MS/MS

2005HAM/COL

37.6G5.3

157.3G22.2

29.1G0.7

121.6G2.9

ClK–L LZmonopentadecanoin dimer 1,3-dipentadecanoin dimmer 1-stearin-2-palmitin glycerol dimmer

27.3 BrK, BrC–, and BrK–X bonds 27.3.1 Br–X bonds Table 27.3.1 BDEs of Br–X Bonds BDEs (boldfaceZ The broken bonds (boldfaceZdissociated fragment) Br–Br

recommended data; reference in parentheses) kcal/mol (1) 46.333

kJ/mol 193.857

Methods (reference in parentheses) Spectroscopy

(2) 46.333G0.029 193.859G0.120

References (1) 1979HUB/HER (2) 2000FOC/LI

(continued)

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

1400

Comprehensive Handbook of Chemical Bond Energies

Table 27.3.1 (continued) BDEs of Br–X Bonds BDEs (boldfaceZ recommended data;

The broken bonds

Methods

reference in parentheses)

(boldfaceZdissociated fragment)

kcal/mol

(reference in

kJ/mol

parentheses)

References

Br2–Br

3

13

Est. by exp.

1989KAW/SAT

Br2–He

0.05, at 0 K

0.20

Spectroscopy

1994JAH/CLE

Br2–He, linear

0.049G0.02,

0.203G0.10

LIF

2005BOU/STR

at 0 K Br2–He, T-shaped

Br2–Ne

0.047G0.02

0.199G0.10

(1) 0.20, at 0 K

0.84

(2) 0.20

0.84

Br–Ar

w1.2

w5.0

Spectroscopy

1994ZHA/YOU

HBr–Ar

0.37, at 0 K

1.56

IR

2005WAN/MCI

Br–Xe

1.42G0.01

5.94G0.02

Spectroscopy

1995CLY/TEL

Br–F

(1) 60.6 (2) 66.9G2.8

253.5 280G12

Spectroscopy

(1) 1976CLY/CUR (2) 1990JEY/RAJ

Br–Cl

(1) 52.0G0.1

217.5G0.3

Spectroscopy

(1) 1979CLY/MCD

(2) 52.42G0.01

219.32G0.05

Br–I

42.8G0.1

179.1G0.4

79

42.8145G0.0005

179.1359G0.0023 PD

81

42.8168G0.0014

179.1453G0.0060

Br–I Br–I

Spectroscopy

(1) 1985THO/EVA (2) 1997SAT/STE

(2) 1995TEL

Spectroscopy

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

1991RAJ/PAL

2000WRE/LAU

BDEs in the Halogenated Molecules, Clusters and Complexes

Br–H

1401

(1) 87.56

366.35

(1) Spectroscopy

(1) 1979HUB/HER

(2) 85.1G0.7

355.9G2.9

(2) PD

(2) 1985NEE/SUT

(3) 87.51G0.05

366.16G0.20

(3) Derived from DfH0 from ref.

(3) 2004SHE/YUN

Br–D

88.61

370.74

Spectroscopy

1979HUB/HER

–T

89.09

372.77

Br–BrF

70.2

293.7

Derived from DfH0

1996NIST

from ref. –BrCl

Br–CH3SCH3

32.7

136.8

12G1

50.2G4.2

Spectroscopy

2001NAK/GOT

27.3.2 BrC–X bonds Table 27.3.2 BDEs of BrD–X Bonds

The broken bonds (boldfaceZdissociated fragment) BrC–Br

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) 76.21G0.07

kJ/mol 318.88G0.23

(2) 76.209G0.006 318.858G0.024

Methods (reference in parentheses)

References

(1) Derived from IP in ref. (2) REMPI

(1) 1996NIST (2) 2003BEC/GRE

BrC–F

(1) 60.2 (2) 65.9G3

251.8 275.5G12.6

(1) Derived (2) Derived from IP in ref.

(1) 1979HUB/HER (2) 1996NIST

BrC–Cl

(1) 71.0G2.3

296.9G9.6

(1) Derived from IP in ref. (2) Photofrag.

(1) 1996NIST

(1) Review (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

(2) 72.418G0.011 303.000G0.048

BrC–H

(1) 90.67G0.07 (2) 90.64G0.69

379.36G0.29 379.26G2.89

(2) 2004NAH/VIE

(continued)

7366—CHAPTER 27—5/2/2007—09:57—JEBA—15383—XML MODEL B – pp. 1351–1427

1402

Comprehensive Handbook of Chemical Bond Energies

Table 27.3.2 (continued) BDEs of BrC–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

Methods (reference in parentheses)

kJ/mol

References

BrC–C

107.9G2.1

451.5G8.6

Derived from IP in ref.

1996NIST

BrC–O

87.4G0.7

365.7G3.1

Derived from IP in ref.

1996NIST

HBrC–HBr

23

96

PI

1979TIE/AND

27.3.3 BrK–X bonds Table 27.3.3 BDEs of BrL–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

BrK–Br

(1) 20.6G1.0 86.2G4.2 (2) 24.57G0.23 102.82G0.96

(1) Derived (2) Derived from EA in ref.

(1) 1974GUR/KAR (2) 1996NIST

BrK–F –Cl

55G5 68G5

230G21 285G21

Derived

1974GUR/KAR

BrK–I

26.3G2.4

110G10

Derived

2004ANG/ERV

BrK–Li

37.8G1.4

158.0G5.7

Derived from EA in ref.

1996NIST

BrK–Na –K –Rb –Cs

27.4G0.7 27.2G0.7 26.6G1.0 29.8G1.0

114.8G2.9 113.8G2.9 111.3G4.2 124.7G4.2

PES

1986MIL/LEO

7366—CHAPTER 27—5/2/2007—09:58—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1403

BrK–Pb

2.6G5

10.8G21

Derived from EA in ref.

1996NIST

BrK–Ar

(1) 1.36 (2) 0.8

5.7 3.3

(1) MS (2) PES

(1) 1986KEE/CAS (2) 1994ZHA/YOU

BrK–Kr

(1) 2.01 (2) 1.10G0.1

8.4 4.6G0.4

(1) MS (2) Laser PES

(1) 1986KEE/CAS (2) 1998YOU/LEN

BrK–Xe

(1) 3.35 (2) 2.9G0.1

14.0 12.1G0.4

(1) MS (2) Laser PES

(1) 1986KEE/CAS (2) 1998YOU/LEN

BrK–O

32.7G0.7

136.9G2.9

Derived

1992GIL/POL

BrK–H2

1.04, at 0 K

4.37

Photofrag.

2003WIL/LOH

BrK–BrCl

O60

O251

PD

1979LEE/SMI

BrK–BrI

19.9

83.3

Derived

1977FIN/GAT

(1) 26.5 (2) 30.4G1.7 (2) 9.6G1.7

111.0 127G7.1 40G7

(1) Derived (2) CID

(1) 1979HUB/HER (2) 1998NIZ/POM

BrK–D2(para) –D2(ortho)

1.04, at 0 K 1.20

4.35 5.00

IR

2001WIL/WEI(b)

BrK–HF

17.0G2.0

71.1G8.4

NICI

1989CAL/MAS

BrK(HCl)x–HCl xZ0 1

19.6 12.5

82.0 52.3

HP MS

1985CAL/KEB

BrK(Br2)x–Br2 xZ0 1

(continued)

7366—CHAPTER 27—5/2/2007—09:58—JEBA—15383—XML MODEL B – pp. 1351–1427

1404

Comprehensive Handbook of Chemical Bond Energies

Table 27.3.3 (continued) BDEs of BrK–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

BrK(SO2)–HCl

22.4

93.7

HP MS

1985CAL/KEB

BrK(HBr)x–HBr xZ0 1

20.6 11.0

86.2 46.0

HP MS

1985CAL/KEB

BrK(SO2)–HBr

12.2

51.0

HP MS

1985CAL/KEB

BrK(NO)x–NO xZ0 1

3.4 w5.1

14.2 w21.3

HP MS

2000HIR/IIN

BrK(HCN)x–HCN xZ0 1 2 3 4 N

(1) (1) (1) (1) (1) (2)

81.2 68.2 53.6 43.5 33.9 w25

(1) HP MS

(1) 1988MEO/CYB

(2) Extrapolate

(2) This volume

BrK(SO2)x–SO2 xZ0 1 2

19.3G2.0 11.2 8.5

80.8G8.4 46.9 35.6

HP MS

1985CAL/KEB

BrK(HCl)–SO2

12.1

50.6

HP MS

1985CAL/KEB

BrK(HBr)–SO2

10.9

45.6

HP MS

1985CAL/KEB

(1) 6.7 (2) 5.3G2.0

28 22.2G8.4

(1) HP MS (2) PD

(1) 1987HIR/MIZ(b) (2) 1995ARN/BRA

BrK(CO2)x–CO2 xZ0

19.4 16.3 12.8 10.4 8.1 w6

7366—CHAPTER 27—5/2/2007—09:58—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1

(1) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (3)

6.0 5.1G2.0 5.1G2.0 5.2G2.0 4.2G2.0 4.0G2.0 3.6G2.0 3.7G2.0 1.8G2.0 1.8G2.0 0.5G2.0 w5.7

25.1 21.3G8.4 21.3G8.4 21.8G8.4 17.6G8.4 16.7G8.4 15.1G8.4 15.5G8.4 7.5G8.4 7.5G8.4 2.1G8.4 w24

BrK(N2O)x–N2O xZ0 1 2 N

(1) (1) (1) (2)

5.57G0.3 5.39G0.3 4.97G0.3 w4

BrK(CS2)x–CS2 xZ0 1 N

2 3 4 5 6 7 8 9 10 N

1405

(3) Extrapolate

(3) This volume

23.3G1.3 22.6G1.3 20.8G1.3 w 17

(1) HP MS

(1) 1993HIR/ARU

(2) Extrapolate

(2) This volume

(1) 8.3G0.2 (1) 7.3G0.2 (2) w6.4

34.7G0.8 30.5G0.8 w27

(1) HP MS

(1) 1993HIR/FUJ

(2) Extrapolate

(2) This volume

BrK(SCO)x–SCO xZ0 1 2 3 N

(1) (1) (1) (1) (2)

40.2G1.3 33.9G1.3 30.1G1.3 w28 w19

(1) HP MS

(1) 2004HIR/FUJ

(2) Extrapolate

(2) This volume

BrK–SeBr2

26.1G1.4

109G6

CID

2003LOB/HAO

(1) (2) (3) (4) (5) (1) (3) (6)

52.7 54 49.0G1.7 53.1 51.0 51.5 48.5G1.3 51.0

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

BrK(H2O)x–H2O xZ0

1

9.6G0.3 8.1G0.3 7.2G0.3 w6.8 w4.4

12.6 12.9 11.7G0.4 12.7 12.2 12.3 11.6G0.3 12.2

HP MS MS HP MS NICI ICR

(6) PES

1970ARS/YAM 1982BUR/HAY 1988HIR/MIZ 1989CAL/MAS 1996TAN/MOR

(6) 1994MAR/POL

(continued)

7366—CHAPTER 27—5/2/2007—09:58—JEBA—15383—XML MODEL B – pp. 1351–1427

1406

Comprehensive Handbook of Chemical Bond Energies

Table 27.3.3 (continued) BDEs of BrK–X Bonds

The broken bonds (boldfaceZdissociated fragment) 2

3

4 5 6

N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (3) (6) (1) (3) (6) (3) (4) (2) (4) (2) (4) (6) (7)

11.5 11.4G0.3 10.8 10.9 11.0G0.2 6.9 10.8G0.3 6.2 10.3G0.5 6.2 w10.0 2.5G2.3 6.0 w10.5

Methods (reference in parentheses)

References

48.1 47.7G1.3 45.3 45.6 46.0G0.8 28.9 45.2G1.3 26.0 43.1G2.1 26.0 w42 10.5G9.6 25.1 w44

(7) Extrapolate

(7) This volume

kJ/mol

H2 BrOK 4 –H2 O

12.0G1.5

50.2G6.3

HP MS

1995BLA/KLA

BrK–CH2

(1) 24.4G6.4 (2) 21.1G1.6

102G27 88.3G6.7

(1) FT-ICR (2) CID

(1) 1985ING/NIB (2) 1997POU/NAS

BrK–CF3

12.5G4.6

52.1G19.3

Derived

1978COM/REI(b)

BrK–NH3

7.7

32.2

HP MS

1986KEE/CAS

BrK–PBr3

15.5G1.4

65G6

CID

2002HEI/CHE

BrK(HONO2)x–HONO2 xZ0 1

20.0 18.1

83.7 75.7

FA

1977DAV/FEH

BrK–CH4

3.1G0.2

13.0G0.8

HP MS

2001HIR/MIZ

7366—CHAPTER 27—5/2/2007—09:58—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1407

BrK–CBrF3

13.9G0.2

58.2G0.8

HP MS

2006BOG/MCM

BrK–CBr2F2

21.0G1.2

88G5

Derived

2006BOG/MCM

BrK–CHCl3 –CH3Cl

15.8 10.9G1.0

66.1 45.6G4.2

KIM MS HP MS

1993GIL/GRI 1996LI/ROS

BrK–CH3Br

(1) 9.2 (2) 11.2G1.0

38.5 46.9G4.2

HP MS

(1) 1974DOU/ROB (2) 1996LI/ROS

(1) (2) (3) (1) (3) (1) (3) (1) (1) (1) (1) (1) (1) (1) (4)

58.2 63.2G1.7 60.7G0.4 52.3 50.2G0.8 44.4 39.7G2.1 41.4 41.0 38.1 35.6 35.1 34.3 w36 w37

(1) HP MS (2) Photodetach. (3) HP MS

(1) 1991HIR/YAM(b) (2) 1997YAN/LIN (3) 1999BOG/PES

(4) Extrapolate

(4) This volume

12.4

51.9

HP MS

2005BOG/MCM

(1) (2) (3) (4) (5) (1) (3) (1) (2) (6)

54.0 53.1 50.6G1.7 59.8G4.2 56.1G3.8 49.4 48.1G2.9 41.8 43.5G2.9 38.5G1.7

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

BrK(CH3COH)x–CH3OH xZ0

1 2 3 4 5 6 7 8 9 N

BrK(iso-PrCl)–CH3OH

BrK(CH3CN)x–CH3CN xZ0

1 2

13.9 15.1G0.4 14.5G0.1 12.5 12.0G0.2 10.6 9.5G0.5 9.9 9.8 9.1 8.5 8.4 8.2 w8 w8.7

12.9 12.7 12.1G0.4 14.3G1.0 13.4G0.9 11.8 11.5G0.7 10.0 10.4G0.7 9.2G0.4

HP MS ICR PES HP MS Photodetach.

(6) HP MS

1972YAM/KEB 1996TAN/MOR 1996MAR/PER 1996LI/ROS 1997YAN/LIN

(6) 1988HIR/MIZ

(continued)

7366—CHAPTER 27—5/2/2007—09:58—JEBA—15383—XML MODEL B – pp. 1351–1427

1408

Comprehensive Handbook of Chemical Bond Energies

Table 27.3.3 (continued) BDEs of BrK–X Bonds

The broken bonds (boldfaceZdissociated fragment) 3

4 5 6 N

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol (1) (3) (6) (3) (6) (3) (6) (3) (6) (7)

5.5 8.5G0.8 8.7G0.3 5.8G0.9 8.5G0.3 5.6G1.0 8.0G0.2 3.0G1.1 7.7G0.3 w7.9

Methods (reference in parentheses)

References

23.0 35.6G3.3 36.4G1.3 24.3G3.8 35.6G1.3 23.5G4.2 33.5G0.8 12.6G4.6 32.2G1.3 w33

(7) Extrapolate

(7) This volume

kJ/mol

BrK(iso-PrCl)–CH3CN

12.0

50.2

HP MS

2005BOG/MCM

BrK–CH3NO2

9.6G2.0

40.2G8.4

FT-ICR

1996TAN/MOR

BrK(HC(O)OH)x– HC(O)OH xZ0 1

17.2G1.7 9.6G1.7

72G7 40G7

CID

1999WAL/SUN

BrK–HCCH

8.6

36.0

Laser PES

2000WIL/MIL

BrK(C2H4)x–C2H4 xZ0 1 2 3 N

(1) (1) (1) (1) (2)

19.7G1.3 17.6G1.3 15.9G1.3 14.6G1.3 w14

(1) HP MS

(1) 2001HIR/KAT

(2) Extrapolate

(2) This volume

46.9G4.2 50.2G4.2 48.5

HP MS

(1) 1996LI/ROS

BrK–C2H5Cl –C2H5Br

4.7G0.3 4.2G0.3 3.8G0.3 3.5G0.3 w3.2

(1) 11.2G1.0 (1) 12.0G1.0 (2) 11.6

7366—CHAPTER 27—5/2/2007—09:58—JEBA—15383—XML MODEL B – pp. 1351–1427

(2) 1974DOU

BDEs in the Halogenated Molecules, Clusters and Complexes

1409

BrK–CH3CHF2

10.6

44.4

HP MS

2005BOG/MCM

BrK(iso-PrCl)–CH3CHF2

10.2

42.7

HP MS

2005BOG/MCM

(1) (2) (3) (3) (3) (4)

60.2 63.6G2.5 59.0G0.8 48.1G2.5 39.7G1.3 w40

(1) ICR (2) Photodetach. (3) HP MS

(1) 1996TAN/MOR (2) 1997YAN/LIN (3) 1999BOG/PES

(4) Extrapolate

(4) This volume

BrK–C2H5OH xZ0

1 2 N

14.4 15.2G0.6 14.1G0.2 11.5G0.6 9.5G0.3 w9.7

BrK–C2H5NO2

14.6

61.1

ICR

1996TAN/MOR

BrK(Me2SO)x–Me2SO xZ0 1 2 N

(1) (1) (1) (2)

17.3 14.5 13.6 w10.3

72.4 60.7 56.9 w43

(1) HP MS

(1) 1984MAG/CAL

(2) Extrapolate

(2) This volume

BrK(C3H6)x–C3H6 xZ0 1 2 3 4 5 N

(1) (1) (1) (1) (1) (1) (2)

5.5G0.3 5.1G0.3 4.8G0.3 4.7G0.3 4.5G0.3 4.4G0.3 w4

23.0G1.3 21.3G1.3 20.1G1.3 19.7G1.3 18.8G1.3 18.4G1.3 w17

(1) HP MS

(1) 2001HIR/KAT

(2) Extrapolate

(2) This volume

BrK(C3F6)x–C3F6 xZ0 1

9.9G0.3 8.3G0.3

41.4G1.3 34.7G1.3

HP MS

2002HIR/TAK

BrK–n-C3H7Cl

12.1G1.0

50.6G4.2

HP MS

1996LI/ROS

BrK–i-C3H7Cl

12.4G1.0

51.9G4.2

HP MS

1996LI/ROS

(continued)

7366—CHAPTER 27—5/2/2007—09:58—JEBA—15383—XML MODEL B – pp. 1351–1427

1410

Comprehensive Handbook of Chemical Bond Energies

Table 27.3.3 (continued) BDEs of BrK–X Bonds

The broken bonds (boldfaceZdissociated fragment) BrK(M)–i-C3H7Cl MZCH3OH CH3CN CH3CHF2 CH3C(O)CH3

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

10.6 9.9 10.4 10.4

44.4 41.4 43.5 43.5

HP MS

2005BOG/MCM

BrK–n-C3H7Br –i-C3H7Br

(1) 11.6 (1) 12.2 (2) 14.2G1.0

48.5 51.0 59.4G4.2

HP MS

(1) 1974DOU (2) 1996LI/ROS

BrK–n-C3H7OH

16.7G0.4

69.9G1.7

Photodetach.

1997YAN/LIN

(1) (2) (3) (3) (3) (4)

61.1 69.0G5.0 60.2G0.8 51.5G1.3 48.1G3.3 w42

(1) ICR (2) Photodetach. (3) HP MS

(1) 1996TAN/MOR (2) 1997YAN/LIN (3) 1999BOG/PES

(4) Extrapolate

(4) This volume

BrK(L)x–L, LZi-C3H7OH xZ0

1 2 N

14.6 16.5G1.2 14.4G0.2 12.3G0.3 11.5G0.8 w10.2

BrK–CH3C(O)CH3

11.2

46.9

HP MS

2005BOG/MCM

BrK(iso-PrCl)– CH3C(O)CH3

10.7

44.8

HP MS

2005BOG/MCM

BrK–t-C4H9Cl

13.9G1.0

58.2G4.2

HP MS

1996LI/ROS

BrK–t-C4H9Br

(1) (2) (1) (1)

51.9 65.3G4.2 54.0 60.2

HP MS

(1) 1974DOU (2) 1996LI/ROS

–i-C4H9Br –t-C5H11Br

12.4 15.6G1.0 12.9 14.4

7366—CHAPTER 27—5/2/2007—09:58—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

BrK(L)x–L, LZt-C4H9OH xZ0 1 2 N

(1) (1) (1) (2)

BrK–C5F8

BrK–C6H6

15.8G0.2 12.9G0.4 11.6G0.5 w10.8

1411

66.1G0.8 54.0G1.7 48.5G2.1 w45

(1) HP MS

(1) 1999BOG/PES

(2) Extrapolate

(2) This volume

12.7G0.3

53.1G1.3

MS

2005HIR/FUJ

(1) 8.5G1.0 (2) 9.0

35.6G4.2 37.7

HP MS

(1) 1991PAU/KEB (2) 1994HIR/YAM

BrK(C6F6)x–C6F6 xZ0 1

13.9 12.2

58.2 51.0

HP MS

1987HIR/MIZ

BrK–C6H5F –C6H5Cl

10.6G1.6 11.1G1.8

44.4G6.7 46.4G7.5

HP MS

1991PAU/KEB

BrK–C6H5CH3 –C6H5CF3 –C6H5CCl3

8.6G1.8 12.6G1.8 12.4G1.8

36.0G7.5 52.7G7.5 51.9G7.5

HP MS

1991PAU/KEB

BrK–C6H5OH

(1) 20.8G1.8 (2) 19.6

87.0G7.5 82.0

HP MS

(1) 1990PAU/KEB (2) 1991PAU/KEB

BrK–C6F5OH

25.6G1.8

107.1G7.5

HP MS

1991PAU/KEB

BrK–C6H5C(O)H –C6H5C(O)CH3 –C6H5C(O)OH –C6H5CN –C6H5NH2 –C6H5N(CH3)2 –C6H5NO –C6H5NO2 –C6H5OCH3

13.2G1.8 14.1G1.8 18.3G1.8 14.7G1.8 14.6G1.8 11.7G1.8 13.7G1.8 15.0G1.8 11.8G1.8

55.2G7.5 59.0G7.5 76.6G7.5 61.5G7.5 61.1G7.5 49.0G7.5 57.3G7.5 62.8G7.5 49.4G7.5

HP MS

1991PAU/KEB

(continued)

7366—CHAPTER 27—5/2/2007—09:58—JEBA—15383—XML MODEL B – pp. 1351–1427

1412

Comprehensive Handbook of Chemical Bond Energies

Table 27.3.3 (continued) BDEs of BrK–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

BrK–2-F–C6H4OH –3-F–C6H4OH –4-F–C6H4OH

20.9G1.8 23.4G1.8 23.3G1.8

87.4G7.5 97.9G7.5 97.5G7.5

HP MS

1990PAU/KEB

BrK–2-Cl–C6H4OH –3-Cl–C6H4OH –4-Cl–C6H4OH

21.2G1.8 24.1G1.8 24.4G1.8

88.7G7.5 100.8G7.5 102.1G7.5

HP MS

1990PAU/KEB

BrK–2-CN–C6H4OH –3-CN–C6H4OH –4-CN–C6H4OH

27.0G1.8 27.4G1.8 27.8G1.8

113.0G7.5 114.6G7.5 116.3G7.5

HP MS

1990PAU/KEB

BrK–2-CF3–C6H4OH –3-CF3–C6H4OH –4-CF3–C6H4OH

24.1G1.8 25.7G1.8 26.6G1.8

100.8G7.5 107.5G7.5 111.3G7.5

HP MS

1990PAU/KEB

BrK–2-CH3–C6H4OH –3-CH3–C6H4OH

20.6G1.8 20.3G1.8

86.2G7.5 84.9G7.5

HP MS

1990PAU/KEB

BrK–2-CH3O–C6H4OH –3-CH3O–C6H4OH –4-CH3O–C6H4OH

20.6G1.8 22.1G1.8 21.0G1.8

86.2G7.5 92.5G7.5 87.9G7.5

HP MS

1990PAU/KEB

BrK–3-C(O)H–C6H4OH –4-C(O)H–C6H4OH

25.2G1.8 25.8G1.8

105.4G7.5 107.9G7.5

HP MS

1990PAU/KEB

BrK–4-CH3C(O)–C6H4OH

25.1G1.8

105.07.5

HP MS

1990PAU/KEB

BrK–3-NH2–C6H4OH –4-NH2–C6H4OH

20.3G1.8 19.5G1.8

84.9G7.5 81.6G7.5

HP MS

1990PAU/KEB

7366—CHAPTER 27—5/2/2007—09:59—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1413

BrK–3-NO2–C6H4OH –4-NO2–C6H4OH

27.4G1.8 28.4G1.8

114.6G7.5 118.8G7.5

HP MS

1990PAU/KEB

BrK–2-F–C6H4NO2 –3-F–C6H4NO2 –4-F–C6H4NO2

17.6G1.8 17.3G1.8 15.8G1.8

73.6G7.5 72.4G7.5 66.1G7.5

HP MS

1991PAU/KEB

BrK–2-Cl–C6H4NO2 –3-Cl–C6H4NO2 –4-Cl–C6H4NO2

17.1G1.8 17.5G1.8 16.1G1.8

71.5G7.5 73.2G7.5 67.4G7.5

HP MS

1991PAU/KEB

BrK–2-CH3–C6H4NO2 –3-CH3–C6H4NO2 –4-CH3–C6H4NO2

15.5G1.8 15.9G1.8 16.2G1.8

64.9G7.5 66.5G7.5 67.8G7.5

HP MS

1991PAU/KEB

BrK–2-CF3–C6H4NO2 –3-CF3–C6H4NO2 –4-CF3–C6H4NO2

19.2G1.8 18.5G1.8 16.4G1.8

80.3G7.5 77.4G7.5 68.6G7.5

HP MS

1991PAU/KEB

BrK–2-CN–C6H4NO2 –3-CN–C6H4NO2 –4-CN–C6H4NO2

20.9G1.8 20.5G1.8 18.6G1.8

87.4G7.5 85.8G7.5 77.8G7.5

HP MS

1991PAU/KEB

BrK–2-C(O)H–C6H4NO2 –2,4-(CF3)2–C6H3NO2 –1,2-(NO2)2–C6H4 –2,4-(NO2)2–C6H3CN –2,4-(NO2)2–C6H3CF3

18.5G1.8 17.6G1.8 21.0G1.8 21.6G1.8 19.8G1.8

77.4G7.5 73.6G7.5 87.9G7.5 90.4G7.5 82.8G7.5

HP MS

1991PAU/KEB

BrK–1,2-(NO2)2–C6H4 –1,3-(NO2)2–C6H4 –1,4-(NO2)2–C6H4

21.0G1.8 20.3G1.8 18.6G1.8

87.9G7.5 84.9G7.5 77.8G7.5

HP MS

1991PAU/KEB

BrK1,3,5-(NO2)3–C6H3

22.5G1.8

94.1G7.5

HP MS

1991PAU/KEB

7366—CHAPTER 27—5/2/2007—09:59—JEBA—15383—XML MODEL B – pp. 1351–1427

1414

Comprehensive Handbook of Chemical Bond Energies

27.4 I–, IC–, and IK–X bonds 27.4.1 I–X bonds Table 27.4.1 BDEs of I–X Bonds BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

I–I

(1) 36.111 (2) 36.456 (3) 36.39G0.14

151.088 152.534 152.25G0.57

Spectroscopy

(1) 1979HUB/HER (2) 1983TRO/ROY (3) 2005LIU/HSU

I2–I

(1) (2) (3) (4)

22.2 w23.2 21G10 13.8G5.8

Derived

(1) (2) (3) (4)

I2–He

(1) 0.052!, 0 K 0.22! (2) 0.050G0.003 0.211G0.012

Spectroscopy

(1) 1980BLA/DEK (2) 1982SHA/KRO

ClI–He

0.064, at 0 K

0.268

Spectroscopy

2003DAR/CRO

I2–Ne

(1) 0.21!, at 0 K (2) 0.16

0.87!

Spectroscopy

(1) 1982SHA/KRO

0.69

ClI–Ne

0.14, at 0 K

0.58

Review

1988EVA/CLI

I–Ar

(1) 2.4 (2) w1.3

10.0 w5.3

(1) Photolysis (2) Spectroscopy

(1) 1970BUR/LER (2) 1994ZHA/YOU

I2–Ar

0.67, at 0 K

2.81

Review

1988EVA/CLI

(1) 0.486!, at 0 K

2.034!

(1) Fluorescence

(1) 1999MIL/CHU

I2–Ar Linear

5.3 w5.5 5G2.4 3.3G1.4

1958BUN/DAV 1971BLA/BUR 1997DO/KLE 1999TAY/ASM

(2) 2001BUR/KER

7366—CHAPTER 27—5/2/2007—09:59—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

T-shaped

(1) 0.406 (2) 0.669!

1.699 2.799!

BrHI–Ar IHI–Ar

w0.68, at 0 K w0.73

I–Kr

1415

(2) OODR

(2) 2001BUR/HEA

w2.86 w3.06

PES

2000LIU/GOM

1.35

5.67

Spectroscopy

1994ZHA/YOU

I–Xe

w1.7

w6.9

Spectroscopy

1996RAD/TEL

I–F

(1) 67G1 (2) %64.9

280G4 %271.5

Spectroscopy

(1) 1970DAR (2) 1976CLY/MCD

I–Cl

50.5G0.1

211.3G0.4

Spectroscopy

1968GAY

I–35Cl I–37Cl

50.540G0.001 50.551G0.001

211.459G0.001 211.507G0.001

Spectroscopy

1978KIN/MCF

I–Br

(1) 42.5G0.1 (2) 42.8G0.1

177.8G0.4 179.1G0.4

I–79Br I–81Br

42.8145G0.0005 179.1359G0.0023 42.8168G0.0014 179.1453G0.0060

PD

2000WRE/LAU

I–H

(1) 71.321 (2) 71.29G0.02

298.407 298.26G0.10

(1) Spectroscopy (2) Derived from DfH0 from ref.

(1) 1979HUB/HER (2) 2004SHE/YUN

(1) 72.26

302.33

–D

(1) 1970DAR (2) 1991RAJ/PAL

7366—CHAPTER 27—5/2/2007—09:59—JEBA—15383—XML MODEL B – pp. 1351–1427

1416

Comprehensive Handbook of Chemical Bond Energies

27.4.2 IC–X bonds Table 27.4.2 BDEs of ID–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

IC–I

(1) 60.7G0.2 (2) 62.83G0.01

254.0G0.8 262.90G0.04

(1) Derived (2) Derived from DfH0 in ref.

(1) 1974GUR/KAR (2) 1996NIST

IC–F

(1) 66G3 (2) 62.8G0.5

276G13 262.9G2.1

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

IC–Cl

(1) 53.8G0.4 (2) 59.2G0.1

225.1G1.7 247.5G0.4

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 2000YEN/LOP

IC–Br

44.19G0.01

184.90G0.02

ZEKE-PEI

1998BEA/MAC

IC–H

(1) 72.9G0.5 (2) 72.83G0.02

305.0G2.1 304.70G0.10

(1) Derived (2) Derived from IP in ref.

(1) 1974GUR/KAR (2) 1996NIST

IC–O

75.6G2.5

316.3G10.5

Derived from IP in ref.

1996NIST

IC(CH3I)x–CH3 xZ0 1 2

78.9, at 0 K 12.2 27.0

330.0 51.1 112.9

PI

1997RAN/SHU

7366—CHAPTER 27—5/2/2007—09:59—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1417

27.4.3 IK–X bonds Table 27.4.3 BDEs of IL–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

IK–I

24.1G0.1

100.9G0.4

PES

1997ZAN/TAY

IK–F

17.4G0.3

72.8G1.3

Derived from DfH0 in ref.

1996NIST

IK–Li –Na –K –Rb –Cs

30.9G1.1 23.7G0.5 24.0G0.5 23.6G1.0 24.8G1.0

129.3G4.6 99.2G1.9 100.4G1.9 98.7G4.2 103.8G4.2

PES

1986MIL/LEO

IK–Mg

28.0G1.5

117.2G6.3

Derived from EA in ref.

1996NIST

IK–CsI –CsI2

36.1G1.3 27.6G3.0

151.0G5.4 115.5G12.6

MS

1979GUS/GOR

IK–Ar –Kr

1.5 1.9

6.3 7.9

Spectroscopy

1994ZHA/YOU

IK–Xe

(1) 2.1

8.7

PES

(1) 1997BEC/MAR

(2) 1.6 (3) 1.7G0.2 (4) 2.1G0.5

6.7 7.2G0.8 8.8G2.1

1.22

5.11

IK 2 –Ar

(2) 1998LEN/FUR (3) 2001PIV/LEN (4) 2002HEN/CLE

PES

1998ASM/TAY

(continued)

7366—CHAPTER 27—5/2/2007—09:59—JEBA—15383—XML MODEL B – pp. 1351–1427

1418

Comprehensive Handbook of Chemical Bond Energies

Table 27.4.3 (continued) BDEs of IK–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

BrHIK–Ar IHIK–Ar

w1.14 w1.52

w4.78 w6.34

PES

2000LIU/GOM

IK–O

41.6G2.0

174.2G8.4

PES

1992GIL/POL

IK–C

35G10

147G42

Derived from EA in ref.

1996NIST

IK–CsI

30.4

127

Derived

1988BEN/KAP

IK–Cl2

94.4

395

Derived

1977FIN/GAT

IK(I2)x–I2 xZ0 1

30.1G1.4 11.7G1.4

126G6 49G6

CID

1997DO/KLE

IK–H2

0.72, at 0 K

3.03

Photofrag.

2003WIL/LOH

IK–D2(para) –D2(ortho)

0.85, at 0 K 0.67

3.55 2.82

IR

2004WIL/BIE

IK–HF

15.0G2.0

62.8G4.2

NICI

1989CAL/MAS

IK–HCl

(1) 14.2 (2) 14.3 (3) 14.8

59.4 59.8 61.9

(1) HP MS (2) ICR (3) HP MS

(1) 1980KEE/LEE (2) 1985LAR/MCM (3) 1985CAL/KEB

7366—CHAPTER 27—5/2/2007—09:59—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

1419

IK–HBr

16.1

67.4

ICR

1985LAR/MCM

IK–HI

17.0

71.1

ICR

1985LAR/MCM

IK–(IK)2

33.5G3.6

140G15

MS

1984BUR/KUD

IK(NO)x–NO xZ0 1

2.7 3.9

11.3 16.3

HP MS

2000HIR/IIN

IK(HCN)x–HCN xZ0 1 2 3 4 5 6 7 N

(1) (1) (1) (1) (1) (1) (1) (1) (2)

16.8 13.2 11.2 9.2 8.6 7.4 7.4 6.8 w6

70.3 55.2 46.9 38.5 36.0 31.0 31.0 28.5 w25

(1) HP MS

(1) 1988MEO/CYB

(2) Extrapolate

(2) This volume

(1) (2) (3) (4) (5) (2) (3) (4) (2) (3) (4) (2) (3) (4) (2) (3) (4) (3) (4)

5.6 4.7 4.2G2.0 3.2 3.7 4.6 3.6G2.0 2.6 4.5 3.7G2.0 2.2 4.3 3.6G2.0 1.8 w4.2 3.1G2.0 1.7 3.0G2.0 1.8

23.4 19.7 17.6G8.4 13.3 15.4 19.2 15.1G8.4 10.9 18.8 15.5G8.4 9.2 18.0 15.1G8.4 7.5 w17.6 13.0G8.4 7.1 12.6G8.4 7.5

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

IK(CO2)x–CO2 xZ0

1

2

3

4

5

HP MS HP MS PD PES Photodetach.

1980KEE/LEE 1987HIR/MIZ(b) 1995ARN/BRA 2002GOM/TAY 2005BOW/BEC

(continued)

7366—CHAPTER 27—5/2/2007—09:59—JEBA—15383—XML MODEL B – pp. 1351–1427

1420

Comprehensive Handbook of Chemical Bond Energies

Table 27.4.3 (continued) BDEs of IK–X Bonds

The broken bonds (boldfaceZdissociated fragment) 6 7 8 9 10 11 12 N

IK(N2O)x–N2O xZ0 1 2 3 4 5 6 7 8 9 10 11 N

IK(CS2)x–CS2 xZ0 1

IK(SO2)x–SO2 xZ0 1

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(6) Extrapolate

(6) This volume

(3) (4) (3) (4) (3) (3) (3) (3) (3) (6)

3.3G2.0 1.9 3.1G2.0 1.9 2.8G2.0 0.9G2.0 1.0G2.0 1.6G2.0 1.1G2.0 w5.7

13.8G8.4 7.9 12.9G8.4 7.9 11.7G8.4 3.8G8.4 4.2G8.4 6.7G8.4 4.6G8.4 w24

(1) (2) (1) (2) (1) (2) (2) (2) (2) (2) (2) (2) (2) (2) (2) (3)

3.78G0.3 2.7G2.0 3.30G0.3 2.9G2.0 w3.2 2.7G2.0 2.8G2.0 2.7G2.0 2.3G2.0 2.2G2.0 2.1G2.0 2.4G2.0 1.8G2.0 1.1G2.0 1.3G2.0 w4

15.8G1.3 11.3G8.4 13.8G1.3 12.1G8.4 w13.4 11.3G8.4 11.7G8.4 11.3G8.4 9.6G8.4 9.2G8.4 8.8G8.4 10.0G8.4 7.5G8.4 4.6G8.4 5.4G8.4 w17

(1) HP MS (2) PD

(1) 1993HIR/ARU (2) 1995ARN/BRA

(3) Extrapolate

(3) This volume

7.4G0.2 6.75G0.2

31.0G0.8 28.2G0.8

HP MS

1993HIR/FUJ

(1) 12.9 (2) 14.3G2.0 (1) 10.1

54.0 59.8G8.4 42.3

(1) HP MS (2) HP MS

(1) 1980KEE/LEE (2) 1985CAL/KEB

7366—CHAPTER 27—5/2/2007—09:59—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

2

IK(SCO)x–SCO xZ0 1 2 3 N

IK(H2O)x–H2O xZ0

1

2

3 4 5 N

1421

(1) 9.2

38.5

(1) (1) (1) (1) (2)

6.4G0.3 5.8G0.3 5.6G0.3 5.4G0.3 w4.4

26.8G1.3 24.3G1.3 23.4G1.3 22.6G1.3 w19

(1) HP MS

(1) 2004HIR/FUJ

(2) Extrapolate

(2) This volume

(1) (2) (3) (4) (5) (1) (2) (6) (7) (1) (2) (6) (7) (2) (7) (2) (7) (7) (8)

10.2 10.3G0.3 10.4G1.0 10.4 10.1 9.8 9.5G0.2 9.9G0.2 9.5 9.4 9.2G0.2 9.3G0.3 8.5 9.2G0.4 6.9 w9.0 4.2 7.8 w10.5

42.7 43.1G1.3 43.5G4.2 43.5 42.5 41 39.7G0.8 41.4G0.8 39.7 39.3 38.5G0.8 38.9G1.3 35.6 38.5G1.7 28.9 w38 17.4 32.8 w44

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

HP MS HP MS PES ICR Photodetach.

1970ARS/YAM 1988HIR/MIZ 1991MAR/GIN 1996TAN/MOR 2005BOW/BEC

(6) HP MS (7) PD

(6) 1980KEE/GAS (7) 1994MAR/POL

(8) Extrapolate

(8) This volume

IK–H2S

8.8G1.0

36.8G4.2

NICI

1989CAL/MAS

IK–NH3

(1) 7.4 (2) 6.7

31.0 28.0

(1) HP MS (2) Photodetach.

(1) 1987EVA/KEE (2) 2005BOW/BEC

IK–PI3

12.9G2

54G8

CID

2002HEI/CHE

IK–CeI3

67G7

280G29

MS

1976CHA

(continued)

7366—CHAPTER 27—5/2/2007—10:00—JEBA—15383—XML MODEL B – pp. 1351–1427

1422

Comprehensive Handbook of Chemical Bond Energies

Table 27.4.3 (continued) BDEs of IK–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

IK(DyI3)x–DyI3 xZ0 1

66.7G2.0 45.2G0.6

279.0G8.4 189.1G2.5

MS

1984LEL/KOR

IK(HoI3)x–HoI3 xZ0 1

69.1 45.4

289 190

MS

1988BEN/KAP

IK–CF3

7.4G4.6

30.9G19.3

Derived

1978COM/REI(b)

IK–CH4

2.6G0.2

10.9G0.8

HP MS

2001HIR/MIZ

IK–CHF3 –CHCl3

14.1G1.0 12.9G1.0

59.0G4.2 54.0G4.2

NICI

1989CAL/MAS

IK–CH3Br

8.3G0.5

34.7G1.9

PD

1992CYR/BIS

(1) (2) (3) (4) (4)

9.0 8.3G0.5 8.4G0.5 7.8G0.2 7.0G0.2

37.7 34.7G2.1 35.1G2.1 32.6G0.8 29.3G0.8

(1) (2) (3) (4)

HP MS PD PES MS

(1) (2) (3) (4)

1974DOU/ROB 1992CYR/BIS 1995ARN/NEU 2005HIR/FUJ

(1) (2) (3) (4) (2) (4)

11.3 11.2 14.4G0.4 11.9G0.2 11.1 9.5G0.2

47.3 46.9 60.2G1.7 49.8G0.4 46.4 39.7G0.8

(1) (2) (3) (4)

HP MS HP MS Photodetach. HP MS

(1) (2) (3) (4)

1984CAL/BER 1991HIR/YAM(b) 1997YAN/LIN 1999BOG/PES

IK(CH3I)x–CH3I xZ0

1

IK(CH3OH)x–CH3OH xZ0

1

7366—CHAPTER 27—5/2/2007—10:00—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

2 3 4 5 6 7 N

(2) (4) (2) (2) (2) (2) (2) (5)

9.8 7.7G0.6 9.7 9.7 9.6 9.4 w9.1 w8.7

41.0 32.2G2.5 40.6 40.6 40.2 39.3 w38 w37

(1) (2) (3) (4) (5) (1) (2) (4) (5) (1) (2) (5) (2) (5) (5) (2) (5) (5) (6)

11.9 11.0 11.1G0.4 11.9 11.1G0.4 10.5 10.4 11.1G0.4 11.1G0.7 9.3 9.2 9.7G0.7 7.8 7.8G0.1 7.4G0.8 7.1 10.6G0.9 10.6G0.9 w7.9

1423

(5) Extrapolate

(5) This volume

49.8 46.0 46.4G1.7 49.8 46.4G1.7 43.9 43.5 46.4G1.7 46.4G2.9 38.9 38.5 40.6G2.9 32.6 32.6G0.4 31.0G3.3 29.7 44.4G3.8 44.4G3.8 w33

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

(6) Extrapolate

(6) This volume

(1) 18.9 (2) 12.9G2.2 (2) 10.8G2.2

79.1 54G9 45G9

(1) HP MS (2) CID

(1) 1984CAL/KEB (2) 1999WAL/SUN

IK–CH3NO2

12.2G1.0

51.0G4.2

NICI

1989CAL/MAS

IK(C2H4)x–C2H4 xZ0 1 2 3

(1) (1) (1) (1)

15.5G1.3 15.1G1.3 14.6G1.3 14.2G1.3

(1) HP MS

(1) 2001HIR/KAT

IK(CH3CN)x–CH3CN xZ0

1

2

3

4

N

IK(HC(O)OH)x–HC(O)OH xZ0 1

3.7G0.3 3.6G0.3 3.5G0.3 3.4G0.3

HP MS HP MS Laser PES ICR PES

1972YAM/KEB 1994HIR/YAM 1995DES/BAI 1996TAN/MOR 1996MAR/PER

(continued)

7366—CHAPTER 27—5/2/2007—10:00—JEBA—15383—XML MODEL B – pp. 1351–1427

1424

Comprehensive Handbook of Chemical Bond Energies

Table 27.4.3 (continued) BDEs of IK–X Bonds

The broken bonds (boldfaceZdissociated fragment) 4 N

IK(C2H5OH)x–C2H5OH xZ0

1 2

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) Extrapolate

(2) This volume

(1) 3.4G0.3 (2) w3.2

14.2G1.3 w14

(1) (2) (3) (3) (3)

50.6 49.0 54.4G0.8 43.9G0.8 35.1G2.1

(1) HP MS (2) ICR (3) HP MS

(1) 1984CAL/KEB (2) 1996TAN/MOR (3) 1999BOGPES

12.1 11.7 13.0G0.2 10.5G0.2 8.4G0.5

IK–CF3CH2OH –CF3CH2NH2

20.1G1.0 14.1G1.0

84.1G4.2 59.0G4.2

NICI

1989CAL/MAS

IK–CH3C(O)OH

16.9G1.0

70.7G4.2

HP MS

1984CAL/KEB

(1) (2) (1) (1)

15.7 16 12.8 11.6

65.7 66.9 53.6 48.5

HP MS

(1) 1984MAG/CAL (2) 1989CAL/MAS

IK(C3H6)x–C3H6 xZ0 1 2 N

(1) (1) (1) (2)

4.6G0.3 4.5G0.3 4.4G0.3 w4

19.2G1.3 18.8G1.3 18.4G1.3 w17

(1) HP MS

(1) 2001HIR/KAT

(2) Extrapolate

(2) This volume

IK(C3F6)x–C3F6 xZ0 1

8.6G0.3 7.7G0.3

36.0G1.3 32.2G1.3

HP MS

2002HIR/TAK

IK(Me2SO)x–Me2SO xZ0 1 2

7366—CHAPTER 27—5/2/2007—10:00—JEBA—15383—XML MODEL B – pp. 1351–1427

BDEs in the Halogenated Molecules, Clusters and Complexes

IK(–i-C3H7OH)x–iC3H7OH xZ0 1 2 N

(1) (2) (2) (2) (3)

12.2 13.1G0.2 11.0G0.3 9.5G0.7 w10.2

1425

51.0 54.8G0.8 46.0G1.3 39.7G2.9 w42

(1) HP MS (2) HP MS

(1) 1984CAl/KEB (2) 1999BOG/PES

(3) Extrapolate

(3) This volume

IK–(CF3)2CHOH –(CN)2CH2 –CH3C(O)CH3

23.9G1.0 18.9G1.0 12.0G1.0

100.0G4.2 79.1G4.2 50.2G4.2

NICI

1989CAL/MAS

IK–CH3CH2C(O)OH

16.6G1.0

69.5G4.2

HP MS

1984CAL/KEB

(1) 12.1 (2) 13.1G0.3 (2) 11.3G0.4

50.6 54.8G1.3 47.3G1.7

HP MS

(1) 1984CAl/KEB (2) 1999BOG/PES

IK–t-C4F9OH

23.2G1.0

97.1G4.2

NICI

1989CAL/MAS

IK–i-C3H7COOH –i-C4H9COOH –t-C4H9COOH

16.7 15.4 15.4

69.9 64.6 64.4

HP MS

1984CAL/KEB

IK–CH3C(O)CH2C(O)CH3

15.1G1.0

63.2G4.2

NICI

1989CAL/MAS

IK–C5F8

10.0G0.2

41.8G0.8

MS

2005HIR/FUJ

IK–C6H6

(1) 6.1G2.0 (2) 9.1G1.0

25.5G8.4 38.1G4.2

HP MS

(1) 1988HIR/MIZ (2) 1989CAL/MAS

11.0 10.4

46.0 43.5

HP MS

1987HIR/MIZ

IK(L)x–L, LZ–t-C4H9OH xZ0 1

IK(C6F6)x–C6F6 xZ0 1

(continued)

7366—CHAPTER 27—5/2/2007—10:00—JEBA—15383—XML MODEL B – pp. 1351–1427

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Comprehensive Handbook of Chemical Bond Energies

Table 27.4.3 (continued) BDEs of IK–X Bonds

The broken bonds (boldfaceZdissociated fragment) I-

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Y

YZCH3 NH2

IK–YC6H4OH YZH 3-F 4-F 3-Cl 4-Cl 3-CN 4-CN 3-NO2 4-NO2 4-CH3

IK 2 ðCO2 Þx –CO2 xZ0 1 2

(1) 11.0G1.0 (1) 12.9G1.0 (2) 11.5

46.0G4.2 54.0G4.2 48.2

(1) (2) (1) (1) (1) (1) (1) (1) (1) (1) (1)

17.3G1.8 16.8 19.4G1.8 19.6G1.8 21.1G1.8 20.5G1.8 23.0G1.8 23.8G1.8 23.2G1.8 23.2G1.8 16.4G1.8

3.2G0.5 2.6G0.5 2.2G0.5

(1) NICI

(1) 1989CAL/MAS

(2) Photodetach.

(2) 2005BOW/BEC

72.4G7.5 70.4 81.2G7.5 82.0G7.5 88.3G7.5 85.8G7.5 96.2G7.5 99.6G7.5 97.1G7.5 97.1G7.5 68.6G7.5

(1) HP MS (2) Photodetach.

(1) 1990PAU/KEB (2) 2005BOW/BEC

13.4G2.0 10.7G2.0 9.2G2.0

FSEP

2002WES/DAV

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BDEs in the Halogenated Molecules, Clusters and Complexes

1427

27.5 At–X bonds Table 27.5 BDEs of At–X Bonds

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

At–At

(1) w19.1 (2) 30.4

w80 127.4

(1) MS (2) Fitting

(1) 1957DRO/HON (2) 1996DOJ/CHE

AtC–At

(1) 56.2 (2) 51G9

235.3 214G39

(1) Derived (2) Derived from IP in ref.

(1) 1996SMI/YAT (2) 1996NIST

AtK–At

23.5

98.5

Fitting

1996DOJ/CHE

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chapter twenty-eight

BDEs in rare gas atom/ion clusters 28.1 Rare gas atom clusters 28.1.1 Diatomic clusters Table 28.1.1 BDEs in Rare Gas Diatom Clusters BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

He–He

(1) 0.9 (2) 0.91G0.01 (3) 0.910

3.8 3.81G0.03 3.809

(1) Spectroscopy (2) Mol. Beam (3) Recommend

(1) 1979HUB/HER (2) 2000GRI/SCH (3) 2001AND

Ne–Ne

(1) 0.94 (2) 0.973

3.93 4.070

(1) Spectroscopy (2) Re-examined

(1) 1973TAN/YOS (2) 1989AZI/SLA

Ar–Ar

(1) 1.13G0.01 (2) 1.174

4.73G0.04 4.910

(1) Spectroscopy (2) Re-examined

(1) 1988HER/LAR (2) 1993AZI

Kr–Kr

(1) 1.25G0.01 (2) 1.29

5.23G0.02 5.39

Spectroscopy

(1) 1973TAN/YOS(b) (2) 1994ZHA/YOU

Xe–Xe

(1) (2) (3) (4)

6.07 5.93 6.52 6.032

Spectroscopy

(1) (2) (3) (4)

1.45 1.42 1.56 1.442

1994ZHA/YOU 1974FRE/YOS 1976CHA/SHR 1994GRE/WAL

(continued)

1429

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Comprehensive Handbook of Chemical Bond Energies

Table 28.1.1 (continued) BDEs in Rare Gas Diatom Clusters BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Rn–Rn

1.7

7.0

Re-analyzed

1998RUN/PYY

He–Ne

0.93

3.89

Re-analyzed

2003TAN/TOE

He–Ar

(1) 0.93 (2) 0.95

3.89 3.96

(1) Review (2) Re-analyzed

(1) 1974GUR/KAR (2) 2003TAN/TOE

He–Kr

0.95

3.97

Re-analyzed

2003TAN/TOE

He–Xe

(1) 0.9 (2) 0.95

3.8 3.96

(1) Scattering (2) Re-analyzed

(1) 1979HUB/HER (2) 2003TAN/TOE

He–Rn

0.95

3.98

Re-analyzed

2003TAN/TOE

Ne–Ar

(1) (2) (3) (1) (2) (3) (1) (2) (3)

4.15 5.84G0.19 4.27 4.18 5.45G0.39 4.31 4.18 5.07G0.19 4.31

(1) Scattering (2) PI (3) Re-analyzed

(1) 1979HUB/HER (2) 1982PRA/DEH (3) 2003TAN/TOE

–Kr

–Xe

0.99 1.40G0.05 1.02 1.00 1.30G0.09 1.03 1.00 1.21G0.05 1.03

Ne–Rn

1.04

4.36

Re-analyzed

2003TAN/TOE

Ar–Kr

(1) 1.22 (2) 1.22

5.11 5.11

(1) Spectroscopy (2) Re-analyzed

(1) 1994ZHA/YOU (2) 2003TAN/TOE

Ar–Xe

(1) 1.26

5.29

(1) Spectroscopy

(1) 1994ZHA/YOU

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BDEs in Rare Gas Atom/Ion Clusters

1431

(2) 4.98G0.02 (3) 1.26

20.85G0.10 5.28

(2) Spectroscopy (3) Re-analyzed

(2) 2002YOS/HAY (3) 2003TAN/TOE

Ar–Rn

1.3

5.5

Re-analyzed

2003TAN/TOE

Kr–Xe

(1) 1.32 (2) 1.35 (3) 1.35

5.51 5.66 5.66

(1) Spectroscopy (2) Spectroscopy (3) Re-analyzed

(1) 1989BAL/JON (2) 1994ZHA/YOU (3) 2003TAN/TOE

Kr–Rn Xe–Rn

1.4 1.5

6.0 6.5

Re-analyzed

2003TAN/TOE

He–Hg

(1) 1.58 (2) 0.9

6.61 3.8

(1) Review (2) Spectroscopy

(1) 1974GUR/KAR (2) 1988YAM/ISO

Ne–Na

(1) w1.3 (2) w0.9

w5.4 w3.8

Spectrometry

(1) 1977BIT/LAP (2) 1999GIL/TRA

Ne–Mg

w1.0

w4.1

Review

1999GIL/TRA

Ne–Zn

(1) 0.95 (2) 0.94

3.96 3.92

Spectroscopy

(1) 1999MCC/BEL (2) 2000KOP/CZA

Ne–Cd

0.95

3.97

Spectroscopy

1994CZA/KRA

Ne–Hg

(1) 1.0 (2) 1.09 (3) 0.99

4.2 4.56 4.14

Spectroscopy

(1) 1988YAM/ISO (2) 1995OND/YAM (3) 1997TAS/OND

Ne–B

0.95

3.97

LIF

1996YAN/HWA

Ne–Al

0.93

3.9

Spectroscopy

1998YAN/DAG

(continued)

7366—CHAPTER 28—5/2/2007—13:21—KARTHIA—15384—XML MODEL B – pp. 1429–1452

1432

Comprehensive Handbook of Chemical Bond Energies

Table 28.1.1 (continued) BDEs in Rare Gas Diatom Clusters BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ar–Br

w1.2

w5.0

Spectroscopy

1994ZHA/YOU

Ar–I

(1) 2.4 (2) w1.3

10.0 w5.3

(1) Photolysis (2) Spectroscopy

(1) 1970BUR/LER (2) 1994ZHA/YOU

Ar–Li

(1) w1.9 (2) 1.87

w7.9 w7.82

(1) Review (2) Derived from the data in ref.

(1) 1969SCH (2) 2002KER/MAV

Ar–Na

w1.0

w4.2

Review

1999GIL/TRA

Ar–Mg

(1) 1.3 (2) w0.9

5.6 w3.7

(1) PI (2) Review

(1) 1996MAS/BRE (2) 1999GIL/TRA

Ar–Ca

1.06G0.14

4.44G0.60

R2PI

1997KAU/BRE(d)

Ar–Zn

(1) 1.8 (2) 1.2

7.4 5.0

(1) Spectroscopy (2) Review

(1) 1990BEN/BRE (2) 1994CZA/KRA

Ar–Cd

(1) 1.2 (2) 1.33G0.01

5.0 5.57G0.05

(1) Review (2) Spectroscopy

(1) 1994CZA/KRA (2) 2002KOP/LUK

Ar–Hg

(1) (2) (3) (4)

5.29 O9.7 5.20 5.32

Spectroscopy

(1) (2) (3) (4)

Ar–B

(1) 1.18 (2) 1.10

4.94 4.62

Spectroscopy

(1) 1997YAN/DAG (2) 1998STA/KNI

1.26 O2.3 1.24 1.27

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1988YAM/ISO 1990OHS/LID 1997TAS/IND 2002KOP/CZA

BDEs in Rare Gas Atom/Ion Clusters

Ar–Al

(1) (2) (3) (4)

Ar–Ga

1.40 1.24 1.36 1.24

1433

5.87 5.18 5.69 5.18

Spectroscopy

(1) (2) (3) (4)

1990MCQ/GOL 1992HEI/FU 1993STA/SCH 1996STA/KNI

0.95

3.96

Spectroscopy

1998STA/KNI

Ar–In

(1) 2.08 (2) 1.00

8.7 4.18

Spectroscopy

(1) 1989CAL/MIT (2) 1998STA/KNI

Ar–Tl

0.98

4.09

Spectroscopy

1998STA/KNI

Ar–C

1.233

5.158

Spectroscopy

2000LEI/DAG

Ar–Si

1.40

5.86

Spectroscopy

2002TAO/TES

Ar–Ge

!1.3

!5.4

Spectroscopy

2003TAO/DAG

Ar–Sn

!1.2

!5.1

Spectroscopy

2004TAO/DAG

Kr–F

1.6

6.6

Spectroscopy

1994LO/SET

Kr–I

1.35

5.67

Spectroscopy

1994ZHA/YOU

Kr–Li

w2.9

w12.1

Scattering

1974AUE

Kr–Na

w1.08

w4.53

Review

1999GIL/TRA

Kr–K

1.1

4.6

Review

1979HUB/HER

(continued)

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1434

Comprehensive Handbook of Chemical Bond Energies

Table 28.1.1 (continued) BDEs in Rare Gas Diatom Clusters BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Kr–Mg

1.60G0.23

6.71G0.96

Spectroscopy

1997KAU/BRE(c)

Kr–Ca

1.23G0.17

5.15G0.72

R2PI

1997KAU/BRE(d)

Kr–Zn

1.2

5.0

Spectroscopy

1992WAL/RYT

Kr–Cd

(1) (2) (3) (4)

5.27G0.12 5.26 4.98 5.17

Spectroscopy

(1) (2) (3) (4)

Kr–Hg

(1) 2.69 (2) 1.37

11.2 5.75

(1) Review (2) Spectroscopy

(1) 1999GIL/TRA (2) 2001KOP/ATK

Kr–Al

(1) 1.45 (2) 1.45

6.05 6.05

Spectroscopy

(1) 1992HEI/FU (2) 1998STA/KNI

Kr–Ga

0.97

4.08

Spectroscopy

1998STA/KNI

Kr–In

(1) 3.23 (2) 1.16

13.5 4.85

Spectroscopy

(1) 1989CAL/MIT (2) 1998STA/KNI

Kr–Tl

0.99

4.14

Spectroscopy

1998STA/KNI

Kr–O

!2

!8

Review

1974GUR/KAR

Xe–Li

w2.9

w12.1

Scattering

1974AUE

1.26G0.03 1.26 1.19 1.23

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1986BOU 1988WAL/BEN 1991CZA/BOB 1992WAL/RYT

BDEs in Rare Gas Atom/Ion Clusters

1435

Xe–Na

w1.22

w5.12

Review

1999GIL/TRA

Xe–K

1.2

5.0

Review

1979HUB/HER

Xe–Mg

2.32G0.43

9.70G1.79

Spectroscopy

1997KAU/LEU

Xe–Ca

1.75G0.23

7.31G0.96

R2PI

1997KAU/BRE(d)

Xe–Cd

(1) 1.39 (2) 1.56

5.82 6.54

Spectroscopy

(1) 1989FUN/BRE (2) 1994CZA/KRA

Xe–Hg

1.59

6.65

LIF

1986YAM/FUK

Xe–Al

(1) 1.78G0.16 (2) 1.77

7.43G0.69 7.39

Spectroscopy

(1) 1989CAL/MIT (2) 1998STA/KNI

Xe–Ga

1.26

5.27

Spectroscopy

1998STA/KNI

Xe–In

(1) 5.00 (2) 1.55

20.91 6.48

Spectroscopy

(1) 1989CAL/MIT (2) 1998STA/KNI

Xe–Tl

1.00

4.18

Spectroscopy

1998STA/KNI

Xe–F

(1) 3.77 (2) 3.39

15.77 14.18

Spectroscopy

(1) 1981RAO/RED (2) 1994JOH/TEL

Xe–Cl

(1) 1.6 (2) 1.6 (3) 1.69

6.7 6.7 7.08

Spectroscopy

(1) 1979HUB/HER (2) 1980WAY/EDE (3) 1983TEL

Xe–Br

1.42G0.01

5.94G0.02

Spectroscopy

1995CLY/TEL

(continued)

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1436

Comprehensive Handbook of Chemical Bond Energies

Table 28.1.1 (continued) BDEs in Rare Gas Diatom Clusters

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Xe–I

w1.7

w6.9

Spectroscopy

1996RAD/TEL

Xe–O

8.7

36.4

Review

1974GUR/KAR

Xe–N

6.4

26.9

Spectroscopy

1963HER/HER

28.1.2 Polyatomic clusters Table 28.1.2 BDEs in Rare Gas Polyatom Clusters

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

He–HF –DF –HCl

0.02, at 0 K 0.02 0.03

0.08 0.08 0.12

Spectroscopy

1990lOV/NES

He–Cl2

(1) 0.03, at 0 K (2) 0.15 (3) 0.11

0.11 0.65 0.46

(1) Review (2) Spectroscopy (3) Combined

(1) 1988EVA/CLI (2) 1989CLI/SIV (3) 1993BEN/CAS

He–Br2

0.05, at 0 K

0.20

Spectroscopy

1994JAH/CLE

He–Br2, linear

0.049G0.02, at 0 K 0.047G0.02

0.203G0.10

LIF

2005BOU/STR

He–I2

(1) 0.052!, 0 K (2) 0.050G0.003

0.22! 0.211G0.012

Spectroscopy

(1) 1980BLA/DEK (2) 1982SHA/KRO

He–ClI

0.064, at 0 K

0.268

Spectroscopy

2003DAR/CRO

He–Br2, T-shaped

0.199G0.10

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BDEs in Rare Gas Atom/Ion Clusters

1437

He–I35Cl linear T-shaped

0.063G0.006, 0 K 0.056G0.006

0.263G0.024 0.234G0.024

Combined

2004BOU/DAR

He–O2

0.06, at 0 K

0.26

Scattering

1987BEN/CAS

He–N2

0.06, at 0 K

0.23

Scattering

1987BEN/CAS

He–NO

0.06, at 0 K

0.26

Scattering

1987BEN/CAS

He–SO

w0.1, at 0 K

w0.3

Mol. beam

1997AQU/ASC

He–H2O

0.06, at 0 K

0.27

Scattering

2005AQU/COR

He–C6H5NH2

w0.29G0.14, 0 K

w1.2G0.6

R2PI

1984BER/LAW

He–2,3dimethynaphthalene

0.17, at 0 K

0.72

Combined

1997BAC/LEU

Ne–Cl2

0.16, at 0 K

0.66

Review

1988EVA/CLI

Ne–ClI

0.14, at 0 K

0.58

Spectroscopy

1987DRO/LES

Ne–Br2

(1) 0.20, at 0 K (2) 0.20

0.84 0.84

Spectroscopy

(1) 1985THO/EVA (2) 1997SAT/STE

Ne–I2

0.21–0.22, 0 K

0.87–0.89

Spectroscopy

1982SHA/KRO

Ne–ICl

0.14, at 0 K

0.58

Review

1988EVA/CLI

(continued)

7366—CHAPTER 28—5/2/2007—13:21—KARTHIA—15384—XML MODEL B – pp. 1429–1452

1438

Comprehensive Handbook of Chemical Bond Energies

Table 28.1.2 (continued) BDEs in Rare Gas Polyatom Clusters

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ne–O2

0.13, at 0 K

0.58

Scattering

1977LUZ/PIR

Ne–SH

(1) 0.1, at 0 K (2) 0.30

w0.4 1.24

Spectroscopy

(1) 1997YAN/CAR (2) 1999CAR/MIL(b)

Ne–SO

w0.1, at 0 K

w0.5

Mol. beam

1997AQU/ASC

Ne–H2O

0.13, at 0 K

0.55

Scattering

2005AQU/COR

Ne–CH4

w0.1, at 0 K

w0.5

Scattering

1987LIU/LUZ

Ne–cyclo-C3H6

w0.34, at 0 K

w1.44

Spectroscopy

1997XU/JAG

Ne–benzene

(1) w0.4, at 0 K (2) 0.2

w1.7 0.9

(1) FT MW (2) Spectroscopy

(1) 1994BRU/MAK (2) 1995BET/BET

Ne–pyridazine

w0.2, at 0 K

w0.8

Spectroscopy

2000CAM/MEL

Ne–pyridine

0.3, at 0 K

1.1

Spectroscopy

1998MAR/CAM

Ne–pyrimidine

0.3, at 0 K

1.3

Spectroscopy

1999CAM/FAV

Ne–carbazole

!0.61, at 0 K

!2.57

SEP-R2PI

1995DRO/BUR

Ne–fluorene

R0.7, at 0 K

R2.8

Two-photon tech

1983LEU/EVE

Ne–p-difluorobenzene

0.34, at 0 K

1.44

UV fluorescence

2004JAY/PAR

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BDEs in Rare Gas Atom/Ion Clusters

1439

Ne–propylene oxide

0.3, at 0 K

1.1

Spectroscopy

2002BLA/MAR(b)

Ne–2,5-dihydrofuran

0.3, at 0 K

1.1

Spectroscopy

1999MAR/FAV

Ne–dimethylether

0.2, at 0 K

1.0

Spectroscopy

2003MAR/CAM

Ar–Ag2

0.79, at 0 K

3.3

Electron spectra

1991WIL/CHE(b)

Ar–Cl2

0.54, at 0 K

2.25

Spectroscopy

1988EVA/CLI

Ar–I2

0.67, at 0 K

2.81

Review

1988EVA/CLI

Ar–I2 linear T-shaped

at 0 K (1) 0.486–0.497 (1) 0.406 (2) 0.669!

2.034–2.081 1.699 2.799!

(1) Fluorescence

(1) 1999MIL/CHU

(2) OODR

(2) 2001BUR/HEA

Ar–HF

0.29, at 0 K

1.22

IR

1986FRA/PIN

Ar–HCl

(1) 1.1, at 0 K (2) 0.5 (3) 0.33 (4) 1.3

4.6 2.2 1.36 5.4

Spectroscopy

(1) 1963RAN/SIT (2) 1982BOO/EIS (3) 1985HOW/PIN (4) 1988HUT

Ar–ClF

0.66, at 0 K

2.75

Review

1988EVA/CLI

Ar–HBr

0.37, at 0 K

1.56

IR

2005WAN/MCI

Ar–O2

(1) w0.29, at 0 K (2) 0.27

w1.2 1.11

(1) Review (2) Scattering

(1) 1976BLA/EWI (2) 1981PIR/VEC

Ar–OH

(1) 2.1, at 0 K (2) 2.14

8.6 8.97

Spectroscopy

(1) 1993HEA (2) 1999CAR/MIL

(continued)

7366—CHAPTER 28—5/2/2007—13:21—KARTHIA—15384—XML MODEL B – pp. 1429–1452

1440

Comprehensive Handbook of Chemical Bond Energies

Table 28.1.2 (continued) BDEs in Rare Gas Polyatom Clusters

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

Ar–CO

0.3, at 0 K

1.3

Spectroscopy

1995KRA/CRE

Ar–SO

w0.4, at 0 K

w1.6

Mol. beam

1997AQU/ASC

Ar–SH

(1) 1.31, at 0 K (2) 1.64

5.48 6.84

Spectroscopy

(1) 1997YAN/CAR (2) 1999CAR/MIL

Ar–N2

w0.27, at 0 K

w1.13

Review

1976BLA/EWI

Ar–NO

(1) 0.27, at 0 K (2) 0.25 (3) 0.25 (4) 0.257

1.15 1.06 1.05 1.077

(1) Mol. beam (2) MPI (3) R2PI (4) REMPI

(1) 1984CAS/LAG (2) 1989MIL (3) 1994TSU/SHI (4) 2004PAR/CHA

Ar–NaCl

w2, at 0 K

w8

Spectroscopy

1998MIZ/END

Ar–BrHI Ar–IHI

w0.68, at 0 K w0.73

w2.86 w3.06

PES

2000LIU/GOM

Ar–CO2

0.475, at 0 K

1.986

Photofragm.

2000OUD/MIL(b)

Ar–H2O

(1) 0.4, at 0 K (2) 0.3

1.7 1.4

(1) IR (2) Scattering

(1) 1993COH/SAY (2) 2005AQU/COR

Ar–CH4

w0.4

w1.6

Scattering

1987LIU/LUZ

Ar–CH2F2

w0.4, at 0 K

w1.5

Spectroscopy

2000LOP/FAV

Ar–W(CO)5

%3

%13

Est. by exp.

1992WEL/WEI

7366—CHAPTER 28—5/2/2007—13:21—KARTHIA—15384—XML MODEL B – pp. 1429–1452

BDEs in Rare Gas Atom/Ion Clusters

1441

Ar–CF2CH2

0.50, at 0 K

2.10

Spectroscopy

1995BET/BET

Ar–CH3OH –C2H5OH –sec-C4H9OH

0.43, at 0 K 0.50 0.55

1.8 2.1 2.3

Spectroscopy

2004MAR/CAM

Ar–cyclo-C3H6

w0.88, at 0 K

w3.67

Spectroscopy

1997XU/JAG

Ar–Si(CH3)2F2

0.66, at 0 K

2.75

Spectroscopy

2005GIU/OTT

Ar–C6H6

(1) !0.97, at 0 K (2) w1.2 (3) !0.90 (4) !0.97 (5) 0.90

!4.07 w4.9 !3.78 !4.1 3.76

(1) Spectroscopy (2) FT MW (3) Spectroscopy (4) MATI (5) Spectroscopy

(1) 1993KRA/NEU (2) 1994BRU/MAK (3) 1999SAT/PIE (4) 1999NEU/GRE (5) 2003SAM/LAW

Ar–C6H5F

(1) 0.92, at 0 K (2) 0.98

3.84 4.11

MATI

(1) 1996GRE/NEU (2) 1997LEM/BRU

2Ar–C6H5F 3Ar–C6H5F

0.99, at 0 K 1.04

4.15 4.35

MATI

1997LEM/BRU

Ar–p-C6F2H4

(1) w1.1, at 0 K (2) 1.64

w4.7 6.84

Spectroscopy

(1) 1986BUT/CAT (2) 2001BEL/MOU

Ar–p-F–C6H4CH3

0.94G0.06, at 0 K 3.94G0.24

MATI

2004GEO/CHA

Ar–C6H5CH3

0.59–0.72, 0 K

2.45–3.00

LIF

1997KEN/HAA

Ar–C6H5CH2

1.29, at 0 K

5.38

Spectra

1993DIS/BER

Ar–C6H5CHCH2

1.13, at 0 K

4.74

MPI

1988RAD/EVE

(continued)

7366—CHAPTER 28—5/2/2007—13:21—KARTHIA—15384—XML MODEL B – pp. 1429–1452

1442

Comprehensive Handbook of Chemical Bond Energies

Table 28.1.2 (continued) BDEs in Rare Gas Polyatom Clusters

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses)

Methods (reference in parentheses)

kcal/mol

kJ/mol

Ar–anthracene

0.98–2.04, 0 K

4.09–8.52

LIF

1991MUL/HEI

Ar–tetracene

!0.78, at 0 K

!3.28

LIF

1981GRI/FRE

Ar–t-stlbene

1.13–1.70

4.74–7.11

LIF

1990SEM/BAS

Ar–C6H5NH2

1.29, at 0 K

5.38

Spectroscopy

1993HIN/BER

Ar–C6H5CN

!0.57, at 0 K

!2.39

LIF

1987KOB/KAJ

Ar–s-tetrazine

O1.1, at 0 K

O4.6

LIF

1983BRU/KEN

Ar–perylene

1.6–2.0, at 0 K

6.7–8.4

Fluorescence

1989WIT/KAZ

Ar–phenol

1.04G0.04, at 0 K 4.35G1.67

MATI

1999HAI/DES

Ar–furan

(1) w0.67, at 0 K (2) 0.74

w2.82 3.01

Spectroscopy

(1) 1983KUK (2) 1995BET/BET

Ar–pyrrole

0.79, at 0 K

3.33

Spectroscopy

1995BET/BET

Ar–pyrazole

0.8, at 0 K

3.4

Spectroscopy

1998CAM/FAV

Ar–pyridine

(1) w0.66, at 0 K (2) 0.74

w2.78 3.10

Spectroscopy

(1) 1989KLO/EMI (2) 1995BET/BET

Ar–pyrimidine

1.06, at 0 K

4.44

Spectra

1985ABE/OHY

7366—CHAPTER 28—5/2/2007—13:21—KARTHIA—15384—XML MODEL B – pp. 1429–1452

References

BDEs in Rare Gas Atom/Ion Clusters

1443

Ar–fluorene

1.5G0.3, at 0 K

6.1G1.1

Two-photon tech

1983LEU/EVE

Ar–indole

(1) !1.5, at 0 K (2) 1.29G0.04

!6.3 5.39G0.18

(1) PI (2) MATI

(1) 1991OUT/BIC (2) 1998BRA/GRE

Ar–1-methylindole

1.29–1.86, at 0 K

5.39–7.78

PI

1993OUT/DEM

Ar–carbazole

1.52, at 0 K

6.34

SEP-R2PI

1995DRO/BUR

Ar–imidazole

0.9, at 0 K

3.7

Spectroscopy

1998CAM/MEL

Ar–dibenzofuran

%1.49G0.03, at 0 K 1.51G0.05

%6.23G0.14

MATI

1997GRE/STU

6.30G0.22

Kr–Ag2

1.13, at 0 K

4.73

Electron spectra

1991WIL/CHE(b)

Kr–O2

(1) w0.33, at 0 K (2) 0.31

w1.38 1.29

Scattering

(1) 1972TUL/LEE (2) 1998AQU/ASC

Kr–OH

(1) 4.91, at 0 K (2) 5.07

20.55 21.20

Spectroscopy

(1) 1993HEA (2) 1999CAR/MIL

Kr–NO

(1) 0.29, at 0 K (2) 0.31

1.21 1.32

(1) MPI (2) R2PI

(1) 1989MIL (2) 1996BUS/DYK

Kr–SO

w0.5, at 0 K

w2

Mol. beam

1997AQU/ASC

Kr–SH

(1) 3.64, at 0 K (2) 3.69

15.23 15.46

Spectroscopy

(1) 1997YAN/CAR (2) 1999CAR/MIL

Kr–N2

w0.3, at 0 K

w1.3

Mol. beam

1972TUL/LEE

–dibenzo-p-dioxin

(continued)

7366—CHAPTER 28—5/2/2007—13:21—KARTHIA—15384—XML MODEL B – pp. 1429–1452

1444

Comprehensive Handbook of Chemical Bond Energies

Table 28.1.2 (continued) BDEs in Rare Gas Polyatom Clusters

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

Methods (reference in parentheses)

kJ/mol

References

Kr–HF

0.38, at 0 K

1.59

IR

1986FRA/PIN

Kr–ClF

0.83, at 0 K

3.45

Review

1988EVA/CLI

Kr–W(CO)5

!6

!25

Est. by exp.

1992WEL/WEI

Kr–H2O

0.39, at 0 K

1.65

Scattering

2005AQU/COR

Kr–CH4

w0.4, at 0 K

w1.6

Scattering

1987LIU/LUZ

Kr–CH2F2

0.45, at 0 K

1.9

Spectroscopy

2005MAR/MEL

Kr–cyclo-C3H6

w1.01, at 0 K

w4.24

Spectroscopy

1997XU/JAG

Kr–C6H6

(1) w0.93, at 0 K (2) !1.15 (3) w1.5 (4) 0.94

w3.88 4.81 w6.1 3.95

(1) Spectroscopy (2) Spectroscopy (3) FT MW (4) Spectroscopy

(1) 1992KLO/EMI (2) 1993KRA/NEU (2) 1994BRU/MAK (3) 1995BET/BET

Kr–p-C6F2H4

2.06, at 0 K

8.61

Spectroscopy

2001BEL/MOU

Kr–carbazole

1.97, at 0 K

8.23

SEP-R2PI

1995DRO/BUR

Kr–fluorene

R2.0, at 0 K

R8.5

Two-photon tech

1983LEU/EVE

Kr–benzonitrile

!0.57, at 0 K

!2.39

LIF

1987KOB/KAJ

Kr–propylene oxide

0.7, at 0 K

3

Spectroscopy

2002BLA/MAR

7366—CHAPTER 28—5/2/2007—13:21—KARTHIA—15384—XML MODEL B – pp. 1429–1452

BDEs in Rare Gas Atom/Ion Clusters

1445

Kr–oxirane

0.7, at 0 K

3.1

Spectroscopy

2002VEL/MIL

Kr–propylene oxide

0.8, at 0 K

3.5

Spectroscopy

2003BLA/MEL

Kr–dibenzo-p-dioxin

1.83, at 0 K

7.66

Spectroscopy

1995GRE/NEU

Kr–2,5-dihydrofuran

0.8, at 0 K

3.5

Spectroscopy

2000VEL/MEL

Kr–pyridine

w0.92, at 0 K

w3.85

Spectroscopy

1989KLO/EMI

Xe–carbon nanotube

0.4, at 0 K

1.6

NMR

2005CLE/PIE

Xe–Ag2

3.53, at 0 K

14.8

Electron spectra

1992ROB/WIL

Xe–HF

0.52, at 0 K

2.16

IR

1986FRA/PIN

Xe–HCl

(1) 1.6, at 0 K (2) 0.9

6.7 4.0

Spectroscopy

(1) 1963RAN/SIT (2) 1982BOO/EIS

Xe–AuF

w24, at 0 K

w100

Spectroscopy

2004COO/GER

Xe–O2

0.35, at 0 K

1.47

Scattering

1998AQU/ASC

Xe–SO

w0.5, at 0 K

w2.2

Scattering

1997AQU/ASC

Xe–ON

0.35, at 0 K

1.47

MPI

1989MIL

Xe–CH2F2

0.4, at 0 K

1.8

Spectroscopy

2006CAM

Xe–Cr(CO)5

9.0G0.9

37.7G3.8

Transient IR

1992WEL/WEI

(continued)

7366—CHAPTER 28—5/2/2007—13:22—KARTHIA—15384—XML MODEL B – pp. 1429–1452

1446

Comprehensive Handbook of Chemical Bond Energies

Table 28.1.2 (continued) BDEs in Rare Gas Polyatom Clusters BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) –Mo(CO)5

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

8.0G1.0

33.5G4.2

Xe–W(CO)5

(1) 8.2G1.0 (2) 8.4G0.2

34.3G4.2 35.1G0.8

Transient IR

(1) 1992WEL/WEI (2) 1992WEI

Xe–H2O

0.46, at 0 K

1.92

Scattering

2005AQU/COR

Xe–CH4

w0.4, at 0 K

w1.7

Scattering

1987LIU/LUZ

Xe–benzene

(1) w1.8, at 0 K (2) 1.23

w7.6 5.16

(1) FT MW (2) Spectroscopy

(1) 1994BRU/MAK (2) 1995BET/BET

Xe–fluorene

R2.1, at 0 K

R8.8

Two-photon tech

1983LEU/EVE

Xe–carbazole

2.55, at 0 K

10.66

SEP-R2PI

1995DRO/BUR

Xe–oxirane

w0.9, at 0 K

w3.9

Spectroscopy

2002VEL/FAV

28.2 Rare gas ion clusters Table 28.2 BDEs in Rare Gas Ion Clusters BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) HeðHeÞC x –He xZ0

kcal/mol

(1) (2) (3) (4)

58.8 55G1 54.5 57.286G0.005

kJ/mol

Methods (reference in parentheses)

246 230.1G4.2 228 239.687G0.019

(1) Scattering (2) Review (3) HP MS (4) Spectroscopy

7366—CHAPTER 28—5/2/2007—13:22—KARTHIA—15384—XML MODEL B – pp. 1429–1452

References

(1) 1974MIT/WEI (2) 1974GUR/KAR (3) 1990HIR/MOR (4) 1999COM/GUN

BDEs in Rare Gas Atom/Ion Clusters

1 2 3 N

(3) (5) (3) (3) (6)

3.73G0.15 4.2 0.64G0.15 0.48G0.15 w0.02

1447

15.6G0.6 17.6 2.7G0.6 2.0G0.6 w0.1

(5) Ion mobility

(5) 1968PAT

(6) Extrapolate

(6) This volume

HeC–H

296

1239

Derived from DfH0 in ref.

1988LIA/BAR

NeC(He)x–He xZ0 1 2 N

(1) (1) (1) (2)

13.0G0.8 4.6G0.8 1.3G0.8 w0.1

(1) HP MS

(1) 1998HIRSHI

(2) Extrapolate

(2) This volume

NeC 2 ðHeÞx –He xZ0 1

1.4G0.2 0.5G0.2

5.9G0.8 2.1G0.8

HP MS

1998HIRSHI

ArC–He ArC 2 –Ne

0.7G0.2 0.2G0.2

2.9G0.8 0.8G0.8

HP MS

1998HIRSHI

KrC–He

0.5G0.2

2.1G0.8

HP MS

1998HIRSHI

(1) (2) (3) (2) (2) (2) (2) (2) (2) (2) (4)

123.4G7.5 131.4 125.29G1.93 10.3G0.6 3.3G0.6 3.2G0.6 3.2G0.6 3.0G0.6 2.9G0.6 2.6G0.6 w2

(1) PI (2) HP MS (3) Spectroscopy

(1) 1984TRE/POL (2) 1990HIR/MOR (3) 1997RAM/SHE

(4) Extrapolate

(4) This volume

7.5

(1) PI

(1) 1982DEH/PRA(b)

NeðNeÞC x –Ne xZ0

1 2 3 4 5 6 7 N

ArC–Ne

3.1G0.2 1.1G0.2 0.3G0.2 w0.02

29.5G1.8 31.4 29.94G0.46 2.47G0.15 0.79G0.15 0.77G0.15 0.76G0.15 0.72G0.15 0.69G0.15 0.62G0.15 w0.4

(1) 1.8

(continued)

7366—CHAPTER 28—5/2/2007—13:22—KARTHIA—15384—XML MODEL B – pp. 1429–1452

1448

Comprehensive Handbook of Chemical Bond Energies

Table 28.2 (continued) BDEs in Rare Gas Ion Clusters

The broken bonds (boldfaceZdissociated fragment)

BDEs (boldfaceZ recommended data; reference in parentheses) kcal/mol

kJ/mol

Methods (reference in parentheses)

References

(2) 1.8G0.2

7.5G0.8

(2) HP MS

(2) 1998HIR/SHI

(1) 1.27 (2) 0.9G0.2 (2) 0.8G0.2

5.3 3.8G0.8 3.3G0.8

(1) PI (2) HP MS

(1) 1982DEH/PRA(b) (2) 1998HIR/SHI

KrC 2 –Ne

0.6G0.2

2.5G0.8

HP MS

1998HIR/SHI

XeC–Ne

(1) 0.95 (2) 1.78 (3) 0.5G0.2

4.0 7.44 2.1G0.8

(1) PI (2) Fitting cure (3) HP MS

(1) 1982DEH/PRA(b) (2) 1985HAU/MOR (3) 1998HIR/SHI

(1) 29.3 (2) 31.199G0.016 (3) 31.206G0.017 (4) 31.148G0.021 (5) 31.197G0.034 (1) 4.89G0.15 (6) 5.05G0.11 (7) 5.0 (8) 4.15 (1) 1.67G0.15 (1) 1.62G0.15 (9) 2.97 (10) 3.99G0.80 (1) 1.62G0.15 (9) 2.68 (10) 2.76G0.38 (1) 1.59G0.15 (9) 2.61 (10) 2.42G0.08 (1) 1.59G0.15 (9) 2.70 (10) 2.47G0.12 (1) 1.57G0.15

122.6 130.535G0.068 130.566G0.072 130.323G0.087 130.527G0.144 20.4G0.6 21.1G0.5 20.9 17.4 7.0G0.6 6.8G0.6 12.4 16.71G3.34 6.8G0.6 11.2 11.56G1.58 6.7G0.6 10.9 10.12G0.32 6.7G0.6 11.3 10.34G0.49 6.6G0.6

(1) HP MS (2) ZEKE-PFT (3) PES (4) TPEPICO (5) PFI-ZEKE

(1) 1990HIR/MOR (2) 1997SIG/WUE (3) 1998SIG/MER (4) 1999ONU/YOS (5) 2002RUP/MER

(6) MS (7) MS (8) PI

(6) 1979TUR/CON (7) 1979FEH/BRO (8) 1982DEH/PRA

(9) KER (10) KER

(9) 1991WOO/STA (10) 2001PAR/MAT

KrC(Ne)x–Ne xZ0 1

ArC(Ar)x–Ar xZ0

1

2 3

4

5

6

7

7366—CHAPTER 28—5/2/2007—13:22—KARTHIA—15384—XML MODEL B – pp. 1429–1452

BDEs in Rare Gas Atom/Ion Clusters

8

9

10 11 12 13 N

KrC(Ar)x–Ar xZ0

1 2 3 4 N

KrC 2 ðArÞx –Ar xZ0 1 2 3 N

XeC(Ar)x–Ar xZ0

1 2

1449

(9) 2.62 (10) 2.11G0.09 (1) 1.55G0.15 (9) 2.56 (10) 2.86G0.33 (1) 1.55G0.15 (9) 2.30 (10) 2.34G0.01 (9) 2.27 (10) 2.71G0.19 (9) 2.23 (10) 1.98G0.21 (9) 2.13 (10) 2.75G0.45 (9) 1.99 (10) 2.16G0.26 (11) w1.5

10.9 8.84G0.40 6.5G0.6 10.7 11.98G1.38 6.5G0.6 9.6 9.79G0.05 9.5 11.35G0.79 9.3 8.28G0.90 8.9 11.50G1.86 8.3 9.02G1.10 w6

(1) (2) (3) (4) (5) (5) (5) (5) (5) (6)

14.5G0.5 13.1G0.3 14.0G0.1 13.22G0.03 8.6G0.2 5.0G0.2 1.5G0.2 1.4G0.2 1.3G0.2 w1.5

60.6G1.9 54.7G1.4 58.6G0.4 55.31G0.14 36.0G0.8 20.9G0.8 6.3G0.8 5.9G0.8 5.4G0.8 w6

(1) (1) (1) (1) (2)

2.2G0.2 1.6G0.2 1.5G0.2 1.4G0.2 w1.5

9.2G0.8 6.7G0.8 6.3G0.8 5.9G0.8 w6

(1) (2) (3) (4) (5) (5) (5)

4.1 5.7G1.2 4.95G0.28 5.02G0.09 4.9G0.2 3.5G0.2 2.0G0.2

17.2 24G5 20.70G1.12 21.00G0.36 20.5G0.8 14.6G0.8 8.4G0.8

(11) Extrapolate

(11) This volume

(1) PI (2) PI (3) Emission (4) TPEPICO (5) HP MS

(1) 1977NG/TIE (2) 1982DEH/PRA(b) (3) 1991HOL/HUB (4) 1998MOR/TAN (5) 1998HIR/SHI

(6) Extrapolate

(6) This volume

(1) HP MS

(1) 1998HIR/SHI

(2) Extrapolate

(2) This volume

(1) PI (2) SIFT (3) PI (4) UV/SIS (5) HP MS

(1) 1977NG/TIE (2) 1980JON/LIS (3) 1982DEH/PRA(b) (4) 1986HUB/LIP (5) 1998HIR/SHI

(continued)

7366—CHAPTER 28—5/2/2007—13:22—KARTHIA—15384—XML MODEL B – pp. 1429–1452

1450

Comprehensive Handbook of Chemical Bond Energies

Table 28.2 (continued) BDEs in Rare Gas Ion Clusters BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment) 3 4 5 6 7 N

kcal/mol 1.9G0.2 1.9G0.2 1.9G0.2 1.8G0.2 1.8G0.2 w1.5

7.9G0.8 7.9G0.8 7.9G0.8 7.5G0.8 7.5G0.8 w6

XeC 2 ðArÞx –Ar xZ0 1 N

(1) 1.8G0.2 (1) 1.5G0.2 (2) w1.5

7.5G0.8 6.3G0.8 w6

ArC(N2)(Ar)x–Ar xZ0 1 2 N

(1) (1) (1) (2)

6.0 1.7 1.7 w1.5

25.1 7.1 7.1 w6

(1) (2) (1) (1) (1) (1) (3)

26.5 26.498G0.008 5.57G0.15 2.16G0.15 2.05G0.15 2.04G0.15 w2.1

110.9 110.867G0.033 23.3G0.6 9.0G0.6 8.6G0.6 8.5G0.6 w9

(1) (2) (3) (4) (4) (4) (4) (5)

9.4G0.5 9.8G0.3 9.95G0.02 8.1G0.2 4.5G0.2 2.0G0.2 2.0G0.2 w2.1

39.4G1.9 40.9G1.1 41.65G0.08 33.9G0.8 18.8G0.8 8.4G0.8 8.4G0.8 w9

KrðKrÞC x –Kr xZ0 1 2 3 4 N

XeC(Kr)x–Kr xZ0

1 2 3 N

(5) (5) (5) (5) (5) (6)

kJ/mol

Methods (reference in parentheses)

References

(6) Extrapolate

(6) This volume

(1) HP MS

(1) 1998HIR/SHI

(2) Extrapolate

(2) This volume

(1) HP MS

(1) 1997HIR/FUJ

(2) Extrapolate

(2) This volume

(1) HP MS (2) PES

(1) 1990HIR/MOR (2) 2001SIG/HOL

(3) Extrapolate

(3) This volume

(1) PI (2) PI (3) TPEPICO (4) HP MS

(1) 1977NG/TIE (2) 1982DEH/PRA(b) (3) 1999YOS/TAN (4) 1998HIR/SHI

(5) Extrapolate

(5) This volume

7366—CHAPTER 28—5/2/2007—13:22—KARTHIA—15384—XML MODEL B – pp. 1429–1452

BDEs in Rare Gas Atom/Ion Clusters

1451

XeC 2 ðKrÞx –Kr xZ0 1 N

(1) 2.4G0.2 (1) 1.7G0.2 (2) w2.1

10.0G0.8 7.1G0.8 w9

XeðXeÞC x –Xr xZ0 1 2 N

23.8 6.03G0.15 2.64G0.15 (2) w3

NeC–H ArC–H KrC–H XeC–H

(1) HP MS

(1) 1998HIR/SHI

(2) Extrapolate

(2) This volume

99.6 25.2G0.6 11.0G0.6 w12

(1) HP MS

(1) 1990HIR/MOR

(2) Extrapolate

(2) This volume

231.4 138.5 110.9 84.8

968 580 464 355

Derived from DfH0 in ref.

1988LIA/BAR

ArC–H2

22.4

93.7

FA

1987SHU/PAS

KrC–N XeC–N

32.7G3.0 15.9G2.3

136.9G13 66.4G9.6

CID

1995HAY/FRY

(1) (2) (2) (2) (2) (3)

164.0 127.6 31.0 10.9 8.8 w6

(1) FA (2) HP MS

(1) 1987SHU/PAS (2) 1997HIR/FUJ

(3) Extrapolate

(3) This volume

ArC(N2)x–N2 xZ0 1 2 3 N

39.2 30.5 7.4 2.6 2.1 w1.4

ArC(Ar)(N2)x–N2 xZ0 1 2

8.1 3.0 2.2

33.9 12.6 9.2

HP MS

1997HIR/FUJ

ArC(Ar)2(N2)x–N2 xZ0 1

5.0 2.8

20.9 11.7

HP MS

1997HIR/FUJ

(continued)

7366—CHAPTER 28—5/2/2007—13:22—KARTHIA—15384—XML MODEL B – pp. 1429–1452

1452

Comprehensive Handbook of Chemical Bond Energies

Table 28.2 (continued) BDEs in Rare Gas Ion Clusters BDEs (boldfaceZ recommended data; reference in parentheses)

The broken bonds (boldfaceZdissociated fragment)

kcal/mol

kJ/mol

Methods (reference in parentheses)

References

ArC(Ar)3(N2)–N2

5.0

20.9

HP MS

1997HIR/FUJ

ArC(CO)x–CO xZ0 1 N

(1) 18G4 (1) 3 (2) w1.8

75G17 13 w8

(1) PES

(1) 1989NOR/GUO

(2) Extrapolate

(2) This volume

KrC–CO –CO2

24.7G1.8 18.9G0.7

103.3G7.5 79.1G2.9

Ion reactions

1993PRA/JOR

HeK–He

48.4

202.5

Derived

1996SMI/YAT

Note: The BDE data with rare gas atom are also arranged in Chapter 11 through Chapter 27.

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chapter twenty-nine

Heats of formation of atoms, radicals, and ions 29.1 Gaseous atoms Table 29.1 Heats of Formation of Gaseous Atoms DfH0(A) Atoms Ac Ag Al Am Ar As Au B Ba Be Bi Bk Br C Ca Cd Ce Cf Cl Cm Co Cr Cs Cu Dy Er

Kcal/mol 97.0 68.1G0.2 78.9G1.0 67.9 0.0 72.3G3 88.0G0.5 135.0G1.2 42.8G1.2 77.4G1.2 50.1G0.5 74.1 26.74G0.03 171.29G0.11 42.5G0.2 26.72G0.05 100.4G0.5 46.9 28.992G0.002 92.2 102.0 95.0G1.0 18.28G0.24 80.6G0.3 69.4G0.5 75.6G0.5

kJ/mol 406 284.9G0.8 330.0G4.0 284 0.0 302.5G13 368.2G2.1 565G5 179.1G5.0 324G5 209.6G2.1 310 111.87G0.12 716.68G0.45 177.8G0.8 111.80G0.20 420.1G2.1 196 121.301G0.008 386 426.7 397.48G4.2 76.5G1.0 337.4G1.2 290.4G2.1 316.4G2.1

References 1981WAG/EVA 1984COX/WAG 1984COX/WAG 1985KLE/WAR 1984COX/WAG 1969BRE/ROS 1969BRE/ROS 1984COX/WAG 1996NIST 1984COX/WAG 1969BRE/ROS 1985KLE/WAR 1996NIST 1984COX/WAG 1984COX/WAG 1984COX/WAG 1989CHA/GIN 1985KLE/WAR 1984COX/WAG 1985KLE/WAR 1996NIST 1996NIST 1984COX/WAG 1984COX/WAG 1989CHA/GIN 1989CHA/GIN (continued)

1453

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Table 29.1 (continued) Heats of Formation of Gaseous Atoms DfH0(A) Atoms Es Eu F Fe Ga Gd Ge H He Hf Hg Ho I In Ir K Kr La Li Lu Mg Mn Mo N Na Nb Nd Ne Ni Np O Os P Pa Pb Pd Pr Pt Pu Ra Rb Re Rh Rn

Kcal/mol 31.8 42.4G0.5 18.97G0.07 99.3G0.3 65.0 95.0G0.5 88.9G0.7 52.103G0.001 0.0 147.8G1.5 14.67G0.01 71.8G0.5 25.52G0.01 58G1 160G1 21.27G0.2 0.0 103.0G0.5 38.07G0.24 102.2G0.5 35.16G0.2 67.7G1.0 157.50G0.79 112.97G0.096 25.7G0.2 175.2G2 78.1G0.5 0.0 102.8G2.0 111.1 59.5672G0.005 188G1.5 75.6G0.2 134.6 46.65G0.2 90.0G0.5 85.3G0.5 135.2G0.3 82.5 38 19.3G0.2 185G1.5 133G1 0.0

kJ/mol 133 177.4G2.1 79.38G0.30 415.5G1.3 271.96 397.5G2.1 372G3 217.998G0.006 0.0 618.4G6.3 61.38G0.04 300.6G2.1 106.76G0.04 243G4 669G4 89.0G0.8 0.0 431.0G2.1 159.3G1.0 427.6G2.1 147.1G0.8 283.3G4.2 658.98G3.8 472.68G0.40 107.5G0.7 733.0G8 326.9G2.1 0.0 430.1G8.4 464.8 249.229G0.002 787G6.3 316.5G1.0 563.2 195.2G0.8 376.6G2.1 356.9G2.1 565.7G1.3 345 159 80.9G0.8 774G6.3 556G4 0.0

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References 1985KLE/WAR 1989CHA/GIN 1984COX/WAG 1996NIST 1998CHA 1989CHA/GIN 1984COX/WAG 1984COX/WAG 1984COX/WAG 1996NIST 1984COX/WAG 1989CHA/GIN 1984COX/WAG 1969BRE/ROS 1969BRE/ROS 1984COX/WAG 1984COX/WAG 1989CHA/GIN 1984COX/WAG 1989CHA/GIN 1984COX/WAG 1996NIST 1996NIST 1984COX/WAG 1996NIST 1996NIST 1989CHA/GIN 1984COX/WAG 1996NIST 1985KLE/WAR 2006RUS/PIN 1969BRE/ROS 1984COX/WAG 1985KLE/WAR 1984COX/WAG 1969BRE/ROS 1989CHA/GIN 1969BRE/ROS 1985KLE/WAR 1981WAG/EVA 1984COX/WAG 1969BRE/ROS 1969BRE/ROS 1969BRE/ROS

Heats of Formation of Atoms, Radicals, and Ions

Ru S Sb Sc Se Si Sm Sn Sr Ta Tb Tc Te Th Ti Tl Tm U V W Xe Y Yb Zn Zr

155.5G1.5 66.25 63.2G0.6 90.3G1 54.3G1 107.6G2 49.4G0.5 71.99G0.36 39.2G0.4 186.9G0.6 92.9G0.5 162 47.0G0.5 143.9G1.4 113.0G0.7 43.55G0.1 55.5G0.5 127.4G2 123.2G2 203.4G1.5 0.0 101.5G0.5 37.2G0.5 31.17G0.10 145.8G2.0

1455

650.5G6.3 277.17 264.4G2.5 377.8G4 227.2G4 450G8 206.7G2.1 301.2G1.5 164.0G1.7 782.0G2.5 388.7G2.1 678 196.6G2.1 602G6 473G3 182.21G0.4 232.2G2.1 533G8 515.5G8 851.0G6.3 0.0 424.7G2.1 155.6G2.1 130.40G0.40 610.0G8.4

1969BRE/ROS 1984COX/WAG 1969BRE/ROS 1969BRE/ROS 1969BRE/ROS 1984COX/WAG 1989CHA/GIN 1984COX/WAG 1996NIST 1969BRE/ROS 1989CHA/GIN 1981WAG/EVA 1969BRE/ROS 1984COX/WAG 1984COX/WAG 1969BRE/ROS 1989CHA/GIN 1984COX/WAG 1996NIST 1996NIST 1984COX/WAG 1989CHA/GIN 1989CHA/GIN 1984COX/WAG 1996NIST

29.2 Small inorganic radicals in the gas-phase 29.2.1 Metallic radicals Table 29.2.1 Heats of Formation of Metallic Radicals DfH0(R) Inorganic radicals AlH AlH2 AlF AlF2 AlHF AlFCl AlCl AlCl2 AlHCl AlBr AlBr2 AlI

kcal/mol 62G5 66.2G5 K63.5G0.8 K166G10 K43.7G7 K117G15 K12.3G1.5 K67G5 2.5G7 3.8G3 K33.6G12 16.2G1.0

kJ/mol

References

260G20 277G20 265.7G3.4 K695G40 K183G30 K490G63 K51.5G6.3 K280G20 10.5G30 15.9G12.6 K141G50 68G4.2

1998CHA 1996GUR/VEY 1998CHA 1998CHA 1996GUR/VEY 1998CHA 1998CHA 1998CHA 1996GUR/VEY 1998CHA 1996GUR/VEY 1998CHA (continued)

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Table 29.2.1 (continued) Heats of Formation of Metallic Radicals DfH0(R) Inorganic radicals AlI2 AlC AlO AlOH Al(OH)2 Al(OH)Cl AlN AlS BaH BaOH BaF BaCl BaBr BaI BeH BeF BeCl BeBr BeI BeOH BeN CaH CaF CaCl CaBr CaI CaOH CoF2 CoCl CoCl2 CuF CuCl FeF FeCl GaH GaO GaOH GaF % GaF2 GaCl % GaCl2 GaBr % GaBr2 GaI

kcal/mol K8.1G12 164.8G2.4 16.0G2 K43.0G3 K121.3G12 K89.3G10 125G9 57.0G2 50.1G1.4 K53.6G3.6 K77.0G2 K34.0G3 K26.4G10 K10.1G20 76.7G6.9 K40.6G2 14.5G3 28.7G10 40.6G10 K27.4G9 102 54.8G0.5 K65G2 K25G3 K11.8G10 K1.2G20 K46.3G5 K85.2G3 46G3 K22.4G2 K3.0G4 21.8G0.4 11.2G5 60G20 51.2G1.1 35.1G5 K34.3G2.4 K55.6G2.6 K123.5G12 K16.7G1 K52.8G12 K4.3G2.4 K35.6G12 10.7G0.7

kJ/mol K34G50 689.5G10 67G8 K180G13 K508G50 K374G40 523G38 238.5G8.4 209.5G5.9 K224.3G15 K322.2G8.4 K142.3G13 K110.6G42 K42.4G84 321G29 K170G8 60.7G12.6 120G42 170G42 K115G38 427 229.4G2.0 K272G8 K104.6G13 K49G42 K5.0G84 K194G21 K356.5G12.6 193G12.6 K93.7G8 K12.6G16.7 91.1G1.7 46.7G20.9 251G84 214G5 147G20 K144G10 K233G11 K517G50 K69.9G4 K221G50 K18G10 K149G50 44.9G3

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References 1996GUR/VEY 1998CHA 1998CHA 1998CHA 1996GUR/VEY 1996GUR/VEY 1998CHA 1998CHA 1996GUR/VEY 1996GUR/VEY 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1996GUR/VEY 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY

Heats of Formation of Atoms, Radicals, and Ions

%

GaI2 GeH3 GeF2 % GeF3 GeCl GeCl2 % GeCl3 GeBr GeBr2 % GeBr3 GeI GeI2 % GeI3 HgH HgF HgCl HgBr HgI InH InO InOH InF % InF2 InCl % InCl2 InBr % InBr2 InI % InI2 KO LiO LiN MgH MgF MgCl MgBr MgI MgN MoF MoF2 MoF3 MoF4 MoF5 MoCl4 MoCl5 MoBr MoBr2 MoBr3 %

K6.9G12 53.0G2 K137.2G4.8 K192.9G12 16.5G4.3 K40.9G1.2 K64.0G12 32.8G1.2 K14.6G1.2 K28.4G12 50.4G6 12.0G1 10G12 57.0G4 0.7G12 18.7G2.3 24.9G9 31.9G1.1 51.4G0.5 34.9G6 29.7G3.6 K46.2G2.4 K109.2G12 K17.2G1.2 K48.0G12 K12.9G2 K35.8G12 6.3G0.3 K9.3G12 17G10 20.1G5 80G40 40.4G11.5 K56.6G2 K10.4G10 K8.4G10 5.9G10 69G6 67.6G3 K38.9G4 K145G4 K226.5G4 K296.7G1 K92.0G3 K107.0G1 109.3G10 40G20 K2.0G7.9

1457

K29G50 221.8G8.4 K574G20 K807G50 69G18 K171G5 K268G50 137G5 K61G5 K119G50 211G25 50.2G4 42G50 238.5G16.7 2.9G50 78.5G9.6 104.2G38 133.5G4.6 215G2 146G25 124.4G15 K193.4G10 K457G50 K72.1G5 K201G50 K54.1G8.5 K150G50 26.3G1.4 K39G50 71.1G41.8 84.1G20.9 334.7G167 169G48 K236.8G8.4 K43.5G42 K35.3G41.8 24.6G41.8 288.7G25.1 282.8G12.6 K162.8G16.7 K607G16.7 K947.7G16.7 K1241.4G4.2 K384.9G12.6 K447.7G4.2 457.3G42 167.4G84 K8.4G33

1996GUR/VEY 1994BER/ELL 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA (continued)

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Table 29.2.1 (continued) Heats of Formation of Metallic Radicals DfH0(R) Inorganic radicals MoBr4 MoI MoI2 MoI3 MoI4 NaO NiCl NiS PbH PbF PbF2 PbF3 PbCl PbCl2 PbCl3 PbBr PbBr2 PbBr3 PbI PbI2 PbI3 SnF SnF2 SnF3 SnCl SnCl2 SnCl3 SnBr SnBr2 SnBr3 SnI SnI2 SnI3 SrH SrOH SrF SrCl SrBr SrI TiF TiF2 TiF3 TiCl TiCl2

kcal/mol K40.9G2 119.2G10 61.6G10 43.7G10 29.8G10 20G10 43.5G1 85.4G4 56.5G4.6 K19.2G2.5 K104G2 K117G14.3 3.6G12 K41.6G0.3 K42.5G19 16.9G10 K25.0G1.5 K24.9G19 25.7G9 K0.76G1 5.2G19 K22.7G1.7 K122.1G2.2 K154.6G12 8.4G2.9 K48.4G1.7 K69.8G12 18.2G2.9 K28.4G0.7 K38G12 41.3G2.9 K1.9G1 K1.9G12 52.4G0.7 K46.4G2.4 K70.4G2 K29.6G2 K21.3G10 K7.3G20 K16G10 K164.5G10 K284.1G10 36.9G10 K56.7G4

kJ/mol K171.1G8 498.7G41.8 257.7G41.8 182.8G41.8 124.7G41.8 83.7G41.8 182.0G4.2 357.4G16.7 236.2G19.2 K80.3G10.5 K435.1G8.4 K490G60 15.1G50 K174.1G1.3 K178G80 70.9G42 K104.4G6.3 K104G80 107.4G37.7 K3.2G4.2 22G80 K95G7.2 K511G9.2 K647G50 35G12 K202.6G7.1 K292G50 76G12 K119G2.8 K159G50 173G12 K8.1G4.2 K8G50 219.2G3.1 K194.1G10 K294.6G8.4 K123.9G8.4 K89.1G42 K30.5G83.7 K66.9G41.8 K688.3G41.8 K1188.7G41.8 154.4G41.8 K237.2G12.6

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References 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1198CHA 1998CHA 1998CHA 1998CHA 1991GUR/VEY 1998CHA 1998CHA 1991GUR/VEY 1998CHA 1998CHA 1991GUR/VEY 1998CHA 1998CHA 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1996GUR/VEY 1996GUR/VEY 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA

Heats of Formation of Atoms, Radicals, and Ions

TiCl3 TiBr TiBr2 TiBr3 TiI TiI2 TiI3 TlH TlOH TlF TlCl TlBr TlI WF WCl WCl2 WBr ZrH ZrF ZrF2 ZrF3 ZrCl ZrCl2 ZrCl3 ZrBr ZrBr2 ZrBr3 ZrI ZrI2 ZrI3 ZrN

K128.9G1.5 50.8G10 K42.8G5 K89.6G3 65.5G10 K4.7G8 K35.9G8 49.0G0.4 K26.3G7 K44.7G0.8 K16.0G0.3 K8.2G0.1 3.8G0.1 92.3G15 132.3G10 K3G25 140G20 123.4 19.8G5 K133.4G5 K264.2G5 49.1G5 K44.5G5 K125.3G5 72G10 K41.7G10 K103 141.3G10 K15.9 K53 170.5

1459

K539.3G6.3 212.5G42 K179.1G20.9 K374.9G10.5 274.1G41.8 K19.7G33.5 K150.2G33.5 204.8G1.5 K110G30 K186.9G3.4 K66.9G1.1 K34.3G0.6 15.9G0.5 386.2G62.8 553.5G41.8 K12.6G105 586G84 516.3 82.8G20.9 K558.1G20.9 K1105.4G21 205.4G20.9 K186.2G20.9 K524.3G20.9 301.2G42 K174.5G42 K431 591.2G41.8 K66.6 K221.8 713.4

1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1996GUR/VEY 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA

29.2.2 Non-metallic radicals Table 29.2.2 Heats of Formation of Non-Metallic Radicals DfH0(R) Inorganic radicals AsH AsH2 BH BH2 BF BF2 BCl

kcal/mol 40.1 40.1G0.3 105.8G2 48G15 K27.7G3.3 K124G9 33.8

kJ/mol

References

167.8 167.8G1.3 442.7G8.4 201G63 K116G14 K519G38 141.4

1988BER 1994BER/ELL 1998CHA 1998CHA 1998CHA 1962MAR 1998CHA (continued)

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Table 29.2.2 (continued) Heats of Formation of Non-Metallic Radicals DfH0(R) Inorganic radicals BCl2 BBr BBrF BBrCl BBr2 BI BI2 BO BS BN BC C2 C3 C4 C5 C6 C7 NSi PH PH2 PF PF2 PCl PCl2 PFCl PBr HSe SP SbH2 HPO HTe

kcal/mol K19G3 56G10 K57.5G2.4 K2.5 15G3.6 72.9G10 58G15 0G2 K166G6 59.97G0.32 198.0G9.8 195.3G2 198.6G3 251.4G3.8 258.4G3.8 313.6G4.3 316.7G4.3 89G15 55.8G8 33.1G0.6 K12.5G5 K116.7G5 30.8 K13.0G1.4 K67.6G7 38.9 34.6G0.5 33.1G10 51.5G0.6 K13.6G10 37.9G1.2

kJ/mol K79.5G12.6 234G42 K240.6G10 K10.5 62.8G15 305G42 243G63 0G8 K695G25 K250.91G1.55 828.4G41 817G8 831G13 1052G16 1081G16 1312G18 1325G18 372.4G62.8 233.6G33.5 138.5G2.5 K52.3G20.9 K488.3G20.9 129 K54.3G6 K283G30 162.6 144.8G2.1 138.6G41.8 215.5G2.5 K57G42 158.6G5.0

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References 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA 1994GIN/FIN 1994GIN/FIN 1994GIN/FIN 1994GIN/FIN 1994GIN/FIN 1994GIN/FIN 1998CHA 1998CHA 1994BER/ELL 1998CHA 1998CHA 1998CHA 1989GUR/VEY 1989GUR/VEY 1998CHA 1994BER/ELL 1998CHA 1994BER/ELL 1989GUR/VEY 1994BER/ELL

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1461

29.3 Organic radicals in the gas-phase 29.3.1 C-centered radicals Table 29.3.1 Heats of Formation of C-Centered Radicals DfH0(R) C-Centered radicals CH CH2 (triplet) CH2 (singlet) % CH3, methyl % C2H, acetenyl, CHbC% % C2H2, vinylidene, CH2aC%% % C2H3, vinyl, CH2aC%H % C2H5, ethyl, CH3C%H2 % C3H3, propargyl, CHbCC%H2 % C3H3, CH3CbC% % C3H3, CH2aCaCH%4CHbCC%H2 % C3H3, cyclopro-2-en-1-yl % C3H5, allyl, CH2aCHC%H2 % C3H5, CH3CHaC%H % C3H5, CH3C%aCH2 % C3H5, cyclopropyl n–C3 H$7 , n-propyl, CH3CH2C%H2 i–C3 H$7 , i-propyl, CH3C%HCH3 % n-C4H3, CHbCCHaC%H % i-C4H3, CH2aC%CbCH % C4H5, CH3CbCC%H2 % C4H5, CHbCC%HCH3 % C4H5, %CHaCHCHCH2 % C4H5, CH2aCHC%CH2 % C4H7, CH3CHaCHC%H2 % C4H7, CH2aCHCH2C%H2 % C4H7, CH2aC(CH3)C%H2 % C4H7, CH2aCHC%HCH3 % C4H7, cyclopropylmethyl % C4H7, cyclobutyl n–C4 H$9 , n-butyl, CH3CH2CH2C%H2 i–C4 H$9 , i-butyl, (CH3)2CHC%H2 s–C4 H$9 , s-butyl, CH3C%HCH2CH3 t–C4 H$9 , t-butyl, (CH3)3C% % C5H3, CHbC–CbCC%H2 % C5H3, (CHbC)2C%H % C5H5, CH2aCHCbCC%H2 % C5H5, CH2aCH–C%H–CbCH % C5H5, cyclopenta–1,3-dien-5-yl % C5H7, CH3CbCC%HCH3

kcal/mol 142.4G0.1 93.5G0.4 102.5G0.4 35.06G0.1 135.6G0.5 100.3G4 71.6G0.8 28.4G0.3 81.0G1.0 123G3.0 81.0G1.0 105.1G4.1 40.9G0.7 63.8G1.5 55.3 66.9G2.5 23.9G0.5 21.0G0.7 130.8 119.3 72.8 75.6 87.1 74.9 34.9G2.0 46.0 33.0 32.5 51.1G1.6 52.4G1.0 18.6G0.5 16.7G1.0 16.2G0.5 11.5G0.7 138.4 137.0 84.0 89 65.5G1.7 65.2G2.2

kJ/mol 595.8G0.6 391.2G1.6 428.8G1.6 146.7G0.3 567.4G2.1 419.7G16.7 299.6G3.3 118.8G1.3 339.0G4.2 515G13 339.0G4.2 439.7G17.2 171.0G3.0 267G6 231.4 279.9G10.5 100G2 88G3 547.3 499.2 304.5 316.5 364.4 313.3 146G8 192.5 137.9 136.2 213.8G6.7 219.2G4.2 77.8G2.1 70G4 67.8G2.1 48G3 579.1 573.2 351.5 372.4 274.1G7.3 272.8G9.2

References 2005RUS/BOG 2005RUS/BOG 2005RUS/BOG 2005RUS/BOG 1994MOR/ASH 1999AHM/PET 1994BER/ELL 1997DOB/BEN 1996TSA 1995ROB/POL 1996TSA 1980DEF/MCI 1996TSA 1999TSA 1990TAK 1979BAG/BEN 1996TSA 1988RUS/SEE(b) 2005KLI/MIL 2005KLI/MIL 2004JAN/ROS 2004JAN/ROS 2004JAN/ROS 2004JAN/ROS 1999TSA 1984SCH/HOU 2004JAN/ROS 2004JAN/ROS 1971MCM/GOL 1978APP/KLU 1990WAL/TSA 1999TSA 1992SEA/PIL 1996TSA 2004ROG/MAT 2004ROG/MAT 1992STA/KIN 1988LIA/BAR 2006NUN/AGA 1981KIN/NGU (continued)

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Table 29.3.1 (continued) Heats of Formation of C-Centered Radicals DfH0(R) C-Centered radicals %

C5H7, CHbCC%HC2H5 C5H7, CHbCC%(CH3)2 % C5H7, CH2aCHCHaCHC%H2 % C5H7, (CH2aCH)2C%H % C5H7, CH3CHaCaCHC%H2 % C5H7, spiropentyl % C5H7, cyclopent-1-en-3-yl % C5H9, cyclopentyl % C5H9, CH2aCHC%HCH2CH3 % C5H9, CH3CHaCHC%H(CH3) % C5H9, CH3CHaC(CH3)C%H2 % C5H9, CH2aCHC%(CH3)2 % C5H9, CH2aC(CH3)C%H(CH3) % C5H9, CH2aC(C%H2)CH2CH3 % C5H9, CH2aCH(CH2)2C%H2 nC5 H$11 , CH3CH2CH2CH2C%H2 % C5H11, (C2H5)2C%H % C5H11, (nC3H7)(CH3)C%H % C5H11, (CH3)3C%CH2 % C5H11, (C2H5)(CH3)2C% % C6H5, phenyl % C6H7, cyclohexa-1,3-dien-5-yl % C6H7, cyclohexa-1,4-dien-3-yl % C6H9, CH3CbCC%(CH3)2 % C6H9, (CH2aCH)2C%(CH3) % C6H9, cyclohexa-1-en-3-yl % C6H11, CH2aCH(CH2)3C%H2 % C6H11, CH2aCHC%H(CH2)2CH3 % C6H11, CH2aC(CH3)C%(CH3)2 % C6H11, (CH3)2CaC(CH3)C%H2 % C6H11, (CH3)2CaCHC%H(CH3) % C6H11, (Z)-CH3CHaCHC%(CH3)2 % C6H11, cyclohexyl nC6 H$13 , CH3CH2CH2CH2CH2C%H2 % C6H13, (nC4H9)(CH3)C%H % C6H13, 2-methyl-2-pentyl % C6H13, 3-methyl-3-pentyl % C6H13, 2,3-dimethyl-2-butyl % C7H3, (CHbC)3C% % C7H7, benzyl, C6H5C%H2 % C7H7, quadricyclolan-5-yl % C7H7, quadricyclolan-4-yl % C7H7, norborna-2,5-dien-7-yl % C7H7, cyclohepta-1,3,5-trien-7-yl %

kcal/mol 66.2G2 61.5G2.2 49G3 49.7G1.0 66.9 91.0G1.0 38.4G1.0 25.3G1.0 26.2G2 22 22.0 20.8G2 22.4 27.3 42.9 13 11.2 12 8.7G2 6.9 78.9G0.8 47.6 48.2G1.2 53.0G2.2 46.3 28.6 37.9 21.3 9.0G1.5 9.5G1.5 11.3 13.0 18G1.5 8 7 0.8G2 3.4 0.7G2.4 187.5 49.7G0.4 138.3G1.3 140.4G1.3 122.3G1.9 68.2G3

kJ/mol

References

277.0G8.4 257.3G9.2 205.0G12.6 208.0G4.2 278.0 380.7G4.2 160.7G4.2 105.9G4.2 109.6G8.4 92 92.0 87.0G8.4 93.7 114.2 179.5 54.4 47.0 50.2 36.4G8.4 29 330.1G3.3 199.2 201.7G5.0 221.8G9.2 193.7 119.7 158.6 89.0 37.7G6.3 39.7G6.3 47.3 54.4 75.3G6.3 33.5 29.3 3.3G8.4 14.2 3.1G10 784.5 208.0G1.7 578.6G5.4 587.4G5.4 511.7G7.9 285.3G12.6

1976LOS/TRA 1977KIN 1982MCM/GOL 1991CLA/CUL 2001TUM/DEN 1971FER/WHI 1970FUR/GOL(b) 1982CAS/GRI 1976LOS/TRA 1988LIA/BAR 2001TUM/DEN 1970EGG/JOL 2001TUM/DEN 2001TUM/DEN 1996CAM/AUT 1988LIA/BAR 1996CAM/AUT 1988LIA/BAR 1969LAR/HAR 1999TSA 1994BER/ELL 1991STE/BRO 1986TSA 1981KIN/NGU 1999LAA/MUL 1988BOR/CHE 1996CAM/AUT 2001TUM/DEN 1973ROD/WU 1973ROD/WU 2001TUM/DEN 2001TUM/DEN 1981TSA 1988LIA/BAR 1988LIA/BAR 1983SER/GOR 1996CAM/AUT 2000KIR/KOR 1990TAK 2005RUS/BOG 1996LEE/DEP 1996LEE/DEP 1996LEE/DEP 1980DEF/MCI

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Heats of Formation of Atoms, Radicals, and Ions

%

C7H9, CH2aCH(CHaCH)2CC%H2 C7H9, (CH2aCH)3C% % C7H11, norborn-1-yl % C7H11, cycloheptenyl % C7H13, cycloheptyl % C7H13, cyclo-[C%(CH3)(CH2)5] % C7H13, cyclo-[C%(CH2CH3)(CH2)4] % C7H15, (nC5H11)(CH3)CH% % C7H15, (CH3)2CHCHC%(CH3)2 % C8H7, cubyl % C8H7, C6H5C%aCH2 % C8H7, C6H5CHaCH% % C8H9, C6H5C%H(CH3) % C8H9, C6H5CH2C%H2 % C8H9, p-CH3C6H4C%H2 % C8H9, m-CH3C6H4C%H2 % C8H9, o-CH3C6H4C%H2 % C8H9, 1-vinyl-cyclohexa-2,4-dienyl % C8H9, 2-vinyl-cyclohexa-2,4-dienyl % C8H9, 3-vinyl-cyclohexa-2,4-dienyl % C8H9, 6-vinyl-cyclohexa-2,4-dienyl % C8H13, CH2aCHCHa CHC%H(CH2)2CH3 % C8H13, CH2aCHC%H(CH2)3CHa CH2 % C8H13, bicyclooct-1-yl % C8H15, CH2aCHC%H(CH2)4CH3 % C8H15, (E)-CH3CHaC%(CH2)4CH3 % C8H15, (Z)-(CH3)2C%CHa CHCH(CH3)2 % C8H15, cyclooctanyl % C8H15, cyclo-[C%(CH2CH3)(CH2)5] % C8H15, (E)-cyclo[C%(CH3)CH(CH3)(CH2)4] % C8H15, (Z)-cyclo[C%(CH3)CH(CH3)(CH2)4] % C9H7, indenyl % C9H9, indanyl-1 % C9H11, 2,6-dimethylbenzyl % C9H11, 3,6-dimethylbenzyl % C9H11, 3,5-dimethylbenzyl % C9H11, C6H5C%(CH3)2 % C9H11, o-%C6H4C2H5 % C9H17, cyclononanyl % C10H7, naphth-1-yl % C10H7, naphth-2-yl % C10H11, tetralin-1-yl % C10H13, 1-phenyl-but-4-yl %

1463

60 65.5 32.6G2.5 28.5 12.1G1 5.4 11.2 2 K5.2G1.2 198.6G4 74 92.5 42.0G1.8 56.4G1.8 40 40 40 59.2G3.4 59.7G3.4 64.4G3.4 68.0G3.4 31.2

251.0 274.0 136.4G10.5 119.2 50.6G4.2 22.6 47.0 8.4 K21.8G5.2 831.0G16.7 309.6 387.0 175.7G7.5 236.0G7.5 167.4 167.4 167.4 247.7G14.2 249.8G14.2 269.4G14.2 284.5G14.2 130.5

1996CAM/AUT 1990TAK 1970ONE/BAG 2001TUM/DEN 1971FER/WHI 2001TUM/DEN 2001TUM/DEN 1988LIA/BAR 2004SER/DIN 1997HAR/EMR 1997PON/TAK 1997PON/TAK 2004TOK/LIN 2004TOK/LIN 1986HAY/KRU 1986HAY/KRU 1986HAY/KRU 2004TOK/LIN 2004TOK/LIN 2004TOK/LIN 2004TOK/LIN 2001TUM/DEN

31.2

130.5

2001TUM/DEN

22.0 11.9 7.1 2.2

92.0 49.8 29.7 9.2

1971DAN/TIP 2001TUM/DEN 2001TUM/DEN 2001TUM/DEN

14.2 2.4 K2.1

59.4 10.0 K8.8

2001TUM/DEN 2001TUM/DEN 2001TUM/DEM

1.5

6.3

2001TUM/DEM

71 48.8G2 29.8 29.8 29.8 32.0G1.0 66.8G1.8 12.5 96.0G1.3 95.7G1.4 37G1.2 45.9

297.1 204.2G8.4 124.7 124.7 124.7 133.9G4.2 279.5G7.5 52.3 401.7G5.4 400.4G5.9 154.8G5.0 192.0

1982MCM/GOL 2000DEN/DEN 1980BAR/STE 1980BAR/STE 1980BAR/STE 1997LAA/BOR 2004TOK/LIN 2001TUM/DEN 2000REE/KAS 2000REE/KAS 1997LAA/MUL 1989FRE/OLM (continued)

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Comprehensive Handbook of Chemical Bond Energies

Table 29.3.1 (continued) Heats of Formation of C-Centered Radicals DfH0(R) C-Centered radicals %

C10H13, (C6H5CH2)(C2H5)C%H C10H13, (C6H5CH2CH2)(CH3)C%H % C10H13, (C6H5C%HCH2CH2CH3 % C10H15, 1-adamantyl % C10H15, 2-adamantyl % C10H19, cyclodecanyl % C11H9, 1-naphthylmethyl % C11H21, cycloundecanyl % C12H23, cyclododecanyl % C13H9, 9-fluorenyl % C13H11, (C6H5)2C%H % C13H11, 9-methyl-9-fluorenyl % C14H11, 9,10-dihydroanthracen-9-yl % C15H11, 9-anthracenylmethyl % C15H11, 9-phenanthrenylmethyl % C16H31, CH2aCHC%H(CH2)12CH3 % C19H15, trityl, (C6H5)3C% % C35H25, pentamethylcyclopentadienyl CF CF2 FC%(O) CHF CClF CCl CCl2 ClC%(O) CHCl CClBr CBr CHBr CBr2 CI CI2 % CF3 % CHF2 % CH2F % CClF2 % CCl2F % CBrClF % CHClF % CBrF2 % CCl3 % CHCl2 %

kcal/mol

kJ/mol

References

44.1 44.1 32.2 12.3 14.8 7.7 60.4 1.8 K9.2 71.1 72.2G1.0 64.1 62.4 80.7 74.4 K28.4 93.7G2 16.1

184.5 184.5 134.7 51.5 61.9 32.2 252.7 7.5 K38.5 297.5 302.1G4.2 268.2 261.0 337.6 311.3 K118.8 392.0G8.4 67.4

1989FRE/OLM 1989FRE/OLM 1989FRE/OLM 1986KRU/BEA 1986KRU/BEA 2001TUM/DEN 1982MCM/GOL 2001TUM/DEN 2001TUM/DEN 1994RAK/VER 1991PAR/HAN 1994RAK/VER 1991STE/BRO 1991PAK/HAN 1982MCM/GOL 2001TUM/DEN 1991PAR/HAN 1995ROT/HUN

61.0G2 K43.5G1.5 K38.5G2 34.2G3.0 7.4G3.2 105.9G3.1 54.0 K5.2G0.6 78.0G2.0 63.8 122G15 89.2G4.3 82.1 136.3G8.4 112G14 K111.3G0.5 K57.1G1 K7.6G1 K66.7G2 K21.3G2 K8.5G1.5 K14.5G2.4 K53.7G3 17.0G0.6 20.8G0.4

255.2G8 K182.0G6.3 K161.2G8.4 143.0G12.6 31.0G13.4 443.1G13.0 226 K21.8G2.5 326.4G8.4 267 510G63 373G18 343.5 570G35 468G60 K465.7G2.1 K238.9G4.2 K31.8G4.2 K279.0G8.4 K89.0G8.4 K35.5G6.3 K60.7G10.0 K224.7G12.6 71.1G2.5 87.1G1.6

1998CHA 1998CHA 1997KNY/BEN 1997POU/PAU 1997POU/PAU 1999JES/SQU 2000BOR/ING 1990NIC/KRE 1997POU/PAU 2000BOR/ING 1998CHA 2000BOR/ING 2004ORE/IRO 1991GUR/VEY 1991GUV/VEY 1998RUS/MIC 1983PIC/ROD 1983PIC/ROD 1992MIY/TSC 1992MIY/TSC 2003OWE/NAU 1987TSC/PAD 1993BAU/HUB 1991HUD/JON 2006LAG/BAE(b)

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Heats of Formation of Atoms, Radicals, and Ions

%

CH2Cl CHBrCl % CHBr2 % CBr2Cl % CBrCl2 % CBr3 % CH2Br % CI3 % CHI2 % CH2I % C2F, FCbC% % C2Cl, ClCbC% % C2F3, CF2aC%F % C2F2H, CF2aC%H % C2F2H, CHFaC%F % CCl2H, CHClaC%Cl % CClH2, CH2aC%Cl % C2F5, CF3C%F2 % C2HF4, CF3C%HF % C2HF4, CHF2C%F2 % C2H2F3, CF3C%H2 % C2H2F3, CHF2C%HF % C2H2F3, CH2FC%F2 % C2H2F2Cl, CF2ClC%H2 % C2H3F2, CH3C%F2 % C2H3F2, CHF2C%H2 % C2H3F2, CH2FC%HF % C2H4F, CH3C%HF % C2H4F, CH2FC%H2 % C2F4Cl, CF2ClC%F2 % C2F4Cl, CF3C%FCl % C2F3Cl2, CF3C%Cl2 % C2H2F2Cl, CClF2C%H2 % C2HF3Cl, CClF2C%HF % C2F3ClBr, CF3C%ClBr % C2Cl, ClCbC% % C2Cl3, CCl2aC%Cl % C2Cl5, CCl3C%Cl2 % C2HCl4, CHCl2C%Cl2 % C2HCl4, CCl3C%HCl % C2H2Cl, C%HCHCl % C2H2Cl3, CH2ClC%Cl2 % C2H2Cl3, CHCl2C%HCl % C2H2Cl3, CCl3C%H2 % C2H3Cl2, CH3C%Cl2 % C2H3Cl2, CH2ClC%ClH % C2H3Cl2, CHCl2C%H2 % C2H4Cl, CH3C%HCl %

28.0G0.7 33.5G1.0 45.0G2.2 39G2 29.6G2 51.3 40.9G0.6 101.6G0.7 75.1G0.8 54.9G2 110G5 135.7G6.2 K45.9G2 K22.2G2 K12.1G2 56.1G2 O60 K213.4G1.0 K162.7G2.3 K158.9 K123.6G2 K109 K107.5 K74.3G1.7 K72.3G2 K68.3 K57.0 K16.8G2 K14.2G2 K164 K174.0 K134.8 K75.3G1.4 K107.7G3 K120.5G2 127.6G12 45.4G12 8.4G1.3 5.6G2 12.2 65.7G0.5 6.3 11.1 17.1G2 10.2G0.4 15.6 21.5G0.2 18.3G0.4

1465

117.2G2.9 140G4 188.3G9.2 163G8 124G8 214.8 171.1G2.7 424.9G2.8 314.4G3.3 229.7G8.4 460.0G21.0 568G26 K192.0G8.4 K92.9G8.4 K50.6G8.4 234.7G8.4 O251 K892.9G4.2 K680.8G9.6 K664.8 K517.1G8.4 K456.0 K449.8 K310.9G7.0 K302.5G8.4 K285.8 K238.5 K70.3G8.4 K59.4G8.4 K686.0 K728.0 K564.0 K315.2G6 K450.6G12.6 K504.2G8.4 534G50 190G50 35.1G5.4 23.4G8.4 51.0 274.8G2.0 26.4 46.4 71.5G8 42.5G1.7 65.3 90.1G0.8 76.5G1.6

1996SEE 2006IMR/KOV 1987TSC/PAD 2000SEE 2000SEE 2004JAN/ROS 2003SEE 2002SEE 2002SEE 1988HOL/LOS 1996ZAR/WES 2002ZHU/BOZ(b) 1983SPY/SAU 1981STE/ROW 1981STE/ROW 1981STE/ROW 1989RUS/SEN 1981EVE/WHI 1983MAR/PAR 1996ZAR/WES 1974WU/ROD 1996ZAR/WES 1996ZAR/WES 1994PAD/CHE 1977PIC/ROD 1996ZAR/WES 1996ZAR/WES 1996MIY/OZA 1996MIY/OZA 1972FOO/TAI 2000YAM/FAN 2000YAM/FAN 2005GIA 1998SKO/DYM 1982MCM/GOL 1991GUR/VEY 1991GUR/VEY 1969FRA/HUY 1976LEW 1994FRE/KAB 2005GAO/ALE 1994FRE/KAB 1994FRE/KAB 1988ROD/JER 1996SEE 1994FRE/KAB 2000SEE 1996SEE (continued)

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1466

Comprehensive Handbook of Chemical Bond Energies

Table 29.3.1 (continued) Heats of Formation of C-Centered Radicals DfH0(R) C-Centered radicals %

C2H4Cl, CH2ClC%H2 C2H3Br2, CH3C%Br2 % C2H4Br, BrCH2C%H2 % C2H4Br, CH3C%HBr % C2Br, CBrC% % C2Br3, CBr2C%Br % C2Br5, CBr3C%Br2 % C3H6Cl, CH3CH2C%HCl % C3H6Cl, CH3C%ClCH3 % C3H6Br, C%H2CH2CH2Br % C3H6Br, CH3C%HCH2Br % C3H6Br, CH3CH2C%HBr % C5H2Cl3, 1,3,4trichlorocyclopentadiene-1-yl % C6F5 % CH3O, HOC%H2 % CH2ClO, HOC%ClH % CHCl2O, HOC%Cl2 % CH2ClO, ClOC%H2 % CH2BrO, BrOC%H2 % C2H3O, C%HaCHOH % C2H3O, C%H2CHO % C2H4O, CH3C%%OH, methylhydroxycarbene % C2H5O, CH3C%HOH % C2H4ClO, CH3C%ClOH % C2H4ClO, C%H2CHClOH % C2H3Cl2O, C%H2CCl2OH % C2H5O, C%H2CH2OH % C2H3O, oxiran-2-yl % C3H5O, CH2aCHC%HOH % C3H5O, %CH2C(CH3)OH % C3H7O, CH3CH2C%HOH % C3H7O, (CH3)C%HCH2OH % C3H7O, HOCH2CH2C%H2 % C3H7O, (CH3)2C%OH % C3H7O, %CH2CH(OH)CH3 % C4H9O, %CH2C(OH)(CH3)2 % C6H5O, 6-oxocyclohexa-1,3-dien-1yl % C2H5O3, C%H2OCH2OOH PhCH%OH Ph2C%OH % C2H5O, CH3OC%H2 %

kcal/mol

kJ/mol

References

22.2G0.6 33.5G1.3 32.3 30.3 149.1 92.1 67.7 13.5 7.1G0.2 28.7G0.3 23.1G1.4 25.7G0.6 36.8G5

93.0G2.4 140.2G5.4 135.1 126.8 623.8 385.3 283.3 56.6 29.9G0.6 120.1G1.3 96.7G5.9 107.5G2.5 154G21

1998SEE 1999MIY/TSC 1988HOL/LOS 1990MIY/TSC 2004ORE/IRO 2004ORE/IRO 2004ORE/IRO 1998SEE 2000SEE 2003GAR 2003GAR 2003GAR 2003BUR/KHA

K130.9G2 K4.06G0.2 K14.5G1.8 K22.5G1.8 32.4G2.2 36.1G3.9 28.9G2.6 3.1G0.5 16G4

K547.7G8.4 K17.0G0.7 K60.7G7.5 K94.1G7.5 135.6G9.2 151G16 121G11 13.0G2 66.9G16.7

1974KRE/PRI 2005RUS/BOG 2001SUN/BOZ 2001SUN/BOZ 2001BOZ/JUN 2000ESP 1997FUL/HAM 2006HAS/DEL 2005LIU/GRO

K12.9 K25.9G2.1 K17.5G2.1 K23.8G2.1 K7.5G1.7 35.8G1.5 0G2 K7.9G0.5 K19.4G1.0 K18.8G2 K16.0G2 K23.0 K15.0G2.8 K35.2G2 58.9

K54.0 K108.4G8.8 K73.2G8.8 K99.6G8.8 K31G7 149.8G6.3 0G8.4 K32.9G2 K81G4 K78.7G8.4 K66.9G8.4 K96.4 K62.8G11.7 K147.3G8.4 246.6

2004JAN/ROS 2001SUN/BOZ(b) 2001SUN/BOZ(b) 2001SUN/BOZ(b) 1997FUL/HAM 1984BAL/KEE 1973ALF/GOL 2006HAS/DEL 1999TSA 1992HOL 1992HOL 2004JAN/ROS 2002SUN/BOZ 1992HOL 2003JAN/FAB

K26.2G1 7G2 36.4G1.5 0G1

109.6G4.2 29.3G8.4 152.3G6.3 0G4.2

2000YAM/BOZ 2005BRA/GAL 1992ARN/CAL 1999ATK/BAU

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Heats of Formation of Atoms, Radicals, and Ions

%

C3H7O, CH3OC%HCH3 C3H7O, CH3CH2OC%H2 % C3H7O, C%H2CH2OCH3 % C4H9O, (CH3)2CHOC%H2 % C4H9O, CH3CH2OC%HCH3 % C4H9O, C%H2CH(CH3)OCH3 % C4H9O, (CH3)2C%OCH3 % C5H11O, (CH3)3COC%H2 % C2H5O2, HOCH2C%HOH C%HaCaO, ketenyl HC%(O) FC%(O) C%CO CH3C%(O) CF3C%(O) CH2ClC%(O) CHCl2C%(O) CCl3C%(O) CH3CH2C%(O) CH2CHC%(O) CH2C(CH3)C%(O) CH3CH2CH2C%(O) (CH3)2CHC%(O) (CH3)3CC%(O) C6H5C%(O) HCðOÞCH$2 ClCðOÞCH$2 E-C%HClC(O)H Z-C%HClC(O)H C%Cl2C(O)H E-C%HClC(O)Cl C%H2C(O)F Z-C%HClC(O)Cl C%Cl2C(O)Cl CH3 CðOÞCH$2 CH3C(O)C%HCH3 CH3C(O)C%aCH2 C2H5C(O)C%HCH3 iPrC(O)C%(CH3)2 tC4H9C(O)C%H2 PhC(O)C%H2 PhC(O)C%HCH3 PhC%HC(O)CH2Ph PhC(O)OC%H2 % C(O)OH-trans % C(O)OH-cis % C(O)OCH3 C%H2C(O)OH %

K13.8G2 K10.8G2 K1.7G1.0 K16.8G1.7 K19.4G1.0 K10.1G0.9 K17.3G2.4 K24.5G2.0 K52.6G2 42.4G2.1 10.2G0.1 K38.5G1.9 91.1G0.5 K2.5G0.4 K145.5 K5G3 K4.2G5.5 K4.7 K7.6G0.8 21.2 14G4 K13G1 K15.3G0.9 K24.6G1.5 27.8G2.6 2.5G2.2 K12.6G3.1 K6.5G2.5 K5.6G2.5 K13.3G3.4 K21.2G3.6 K65.3G1.4 K20.3G3.3 K24.3G3.7 K8.1G0.7 K16.8G1.7 27.1 K25.7G5 K41.5G5 K27.6G3 20.2G3 9.9G5 32.1G3 K16.7 RK46.5G0.7 K52.5 K38.6 K59.5G2.9

1467

K57.7G8.4 K45.2G8.4 K7.1G4.2 K70.3G7.1 K81.2G4.2 K42.3G3.8 K72.4G10 K102.5G8.4 K220.1G8.4 177.5G8.8 42.5G0.5 K161.2G8.1 381.2G2.1 K10.3G1.8 K608.7 K21G12.6 K17.6G23 K19.7 K31.7G3.4 88.5 58.6G16.7 54.4G4.2 K64.0G3.8 K102.9G6.3 116.3G10.9 10.5G9.2 K52.7G13 K27.2G10.5 K23.4G10.5 K55.6G14.2 K88.7G15.1 K273.0G5.8 K84.9G13.8 K101.7G15.5 K34G3 K70.3G7.1 113.4 K107.5G20.9 K173.6G20.9 K115.5G12.6 84.5G12.6 41.4G20.9 134.3G20.9 K69.9 RK194.6G2.9 K219.7 K161.5 K248.9G12.0

1984HOL/LOS 1991HOL/LOS 2003CHE/BOZ 2003CHE/BOZ 1986BUR/MAJ 2003CHE/BOZ 2003CHE/BOZ 2003CHE/BOZ 1992HOL 1983OAK/JON 1996TER/KAB 1997KNY/BEN 1998CHO/MOR 2005RUS/BOG 2004JAN/ROS 2002ZHU/BOZ 2002ZHU/BOZ 2004JAN/ROS 2005KER/FOG 2004JAN/ROS 2000VIS/BER 2000VIS/BER 2000VIS/BER 2000VIS/BER 1989SIM/GRI 1994BER/ELL 2002ZHU/BOZ 2002ZHU/BOZ 2002ZHU/BOZ 2002ZHU/BOZ 2002ZHU/BOZ 2004HOO/GAS 2002ZHU/BOZ 2002ZHU/BOZ 2001BOU/CHA 1970SOL/BEN 1990TAK 1990BOR/HAR 1990BOR/HAR 1990BOR/HAR 1990BOR/HAR 1990BOR/HAR 1990BOR/HAR 1970SOL/BEN 2000RUS/LIT 1989RUS/SCH(b) 2004JAN/ROS 1994WEN/SQU(b) (continued)

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Table 29.3.1 (continued) Heats of Formation of C-Centered Radicals DfH0(R) C-Centered radicals C%H(CH3)C(O)OH C%H2C(O)OCH3 C%H2C(O)OCH2CH3 C%H2C(O)OPh % C4H7O, tetrahydrofuran-2-yl % C4H8O, cyclopentanon-2-yl % C4H7O2, 1,4-dioxan-2-yl % C7H5O2, 2-C(O)OH–%C6H4 % C7H5O2, 3-C(O)OH–%C6H4 % C7H5O2, 4-C(O)OH–%C6H4 % CH3O2, C%H2OOH % C2H5O2, C%H2CH2OOH % C2H5O2, CH3CH%OOH % C3H7O2, CH3CH%CH2OOH % C3H7O2, C%H2CH(OOH)CH3 % C4H9O2, (CH3)2C%CH2OOH % C4H9O2, C%H2C(CH3)2OOH % C2H3O3, C%H2C(O)OOH % C6H5O, 2,4-cyclohexadiene-1-one2-yl % C6H4ClO, 2,5-cyclohexadiene-2chloro-1-one-4-yl % C6H4ClO, 2,4-cyclohexadiene-6chloro-1-one-2-yl % C6H4ClO, 5-chloro-6-oxocyclohexa1,3-dien-1-yl % C6H4ClO, 3-chloro-4-oxocyclohexa-2,5-dien-1-yl % C6HCl3OH, 2,4,6-trichlorophenol5-yl % C6HCl3OH, 2,4.6-trichloro-3hydrophynyl % C6H2Cl3O2, 2,4.6-trichlorobicyclo2-hexene-1-one-4,6-peroxy-5-yl C6 H2 Cl3 O$3 , 1,3,5-trichloro-4-oxo6,7-dioxabicyclo[3.2.1]-oct-2-en-8yl % C12H5Cl4O3, 1,3-dichloro-1-ol-2-yl3,5-hexadiene-p-dioxin-6,8dichlorobenzene radical % C12H5Cl4O3, 1,3-dichloro-2-ol-3-yl1,4-hexadiene-p-dioxin-6,8dichlorobenzene radical % CHN2

kcal/mol

kJ/mol

References

K70.0G0.7 K56.6G2 K62.2G3 K6.7 K4.3G1.5 K10G3 K31.5G3 K7.9 K8.4 K8.6 15.8 11.0G1.1 6.4 2.6G1.3 0.7G1.5 K7.2G1.3 K6.4G1.3 K33.0 27.0

K293G3 K236.8G8.4 K260.2G12.6 K28.0 K18.0G6.3 K41.8G12.6 K131.8G12.6 K33.0 K35.0 K36.0 66.1 46.0G4.6 26.9 10.9G5.4 2.9G6.3 K30.1G5.4 K26.8G5.4 K137.9 113.0

2002LAG/DIO 1991HOL/LOS 1995BOR/ZHA 1973ALF/GOL 1982MCM/GOL 1991BOR/GAL 2000KRA/CIR 1998NAS/SQU 1998NAS/SQU 1998NAS/SQU 2004JAN/ROS 2000CHE/BOZ 2004JAN/ROS 2000CHE/BOZ 2000CHE/BOZ 2000CHE/BOZ 2000CHE/BOZ 2002LEE/CHE 2003BUR/KHA

16.2G15

67.8G63

2003BUR/KHA

55G30

230G126

2003BUR/KHA

54.0

225.9

2003JAN/FAB

7.3

30.6

2003JAN/FAB

16.9G5

70.7G21

2003BUR/KHA

24.3

101.5

2003JAN/FAB

K2.1

K8.7

2003BUR/KHA

31.4

131.4

2003JAN/FAB

K103.4G5

K432.6G21

2003BUR/KHA

K77G15

K322G63

2003BUR/KHA

118.2

494.5

1996FUL/HIP

7366—CHAPTER 29—3/2/2007—18:03—CRCPAG—15385—XML MODEL B – pp. 1453–1485

Heats of Formation of Atoms, Radicals, and Ions

%

CH2NaCH2 CH2NH2 CH3C%HNH2 (CH3)2C%NH2 % CH2NHCH3 % CH2N(CH3)2 (C2H5)2NC%HCH3 % CH2N(CH3)Ph % CN % CH2CN CH3C%HCN % CH2CH2CN (CH3)2C%CN Ph(CH3)C%CN NCC%HCH2CN % CH2NC % C(O)NC % C(O)NH2 C%NN HC%NN H2C%NN % CH2NO % CH2NO2 CH3C%HNO2 (CH3)2C%NO2 PhC%HNO2 % C6H6N, 3-NH2–C6H4 % C6H6N, 4-NH2–C6H4 % C6H4NO2, 3-NO2–C6H4 % C6H4NO2, 4-NO2–C6H4 % C6H4CH3, 2-Me–C6H4 % C6H4CH3, 4-Me–C6H4 % C6H3N2O4, 3,5-(NO2)2–C6H3 % C7H6NO2, 2-Me-4-NO2–C6H3 % C4H3N, pyrrol-2-yl % C4H3N, pyrrol-3-yl % C4H8N, pyrrolidin-2-yl % C5H4N, pyrid-2-yl % C5H4N, pyrid-3-yl % C5H4N, pyrid-4-yl % C4H7N2, piperad-2-yl % C4H3N2, pyrazin-2-yl % C4H3N2, pyrimid-2-yl % C4H3N2, pyrimid-4-yl % C4H3N2, pyrimid-5-yl % CH(NO2)2 % C(NO2)3 % CH2C(NO2)3 %

63G3 36.3G2 26.7G2 16.7G2 37.4 35.4 16.4G0.5 63.6G3 105.0G0.7 60.4G1 54.2G3 58.7G3 45.5G3 59.4G2 91.3G3 80G4 50.2G2.4 K3.6G1 136G5 110G2 69.9G0.5 37.5G1 27.5G3 14.8G3 1.5G3 40.4G3 76.5 78.3 81.4G2.4 72.3 75.3G2.5 70.9G2.3 73.0 70.6G2 92.2 92.2 34.1G3 86.5 93.5 93.5 28.6 97.8G3 92.7G3 97.7G3 106.7G3 33.2 48.1 36.0

1469

263.6G12.6 151.9G8.4 111.7G8.4 69.9G8.4 156.6 148.0 68.6G2.1 266.0G12.6 439.3G2.9 252.6G4 226.7G12.6 245.4G12.6 190.4G12.6 248.5G8.4 381.8G12.6 334.7G16.7 210.0G10 K15.1G4 569G21 460G8 292.5G2.1 157G4 115.1G12.6 61.9G12.6 6.3G12.6 169.0G12.6 320.1 327.8 340.6G10.0 302.7 315.1G10.5 296.6G9.6 305.4 295.4G8.4 385.8 385.8 142.7G12.6 362.0 391.0 391.0 119.7 409.2G12.6 388.0G12.6 409.0G12.6 446.4G12.6 139.1 201.2 150.6

1993LAZ/PAP 1983BUR/CAS 1983BUR/CAS 1983BUR/CAS 2004JAN/ROS 2004JAN/ROS 1990DOM/DIN 1999DOM/DIN 2000COO/LAN 2000LAF/SZA 1999SEN/IKE 1999SEN/IKE 1998BRO/BEC 1982MEO 1999SEN/IKE 2002NIM/DAV 2001DOR/NOV 2003NASA/JPL 1998CLI/WEN(b) 1998CLI/WEN(b) 2000BIS/HOO 2003NASA/JPL 1994BOR/SAT 1994BOR/SAT 1994BOR/SAT 1995BOR/ZHA(c) 1975MAT/NAS 1975MAT/NAS 1985GON/LAR 1975MAT/NAS 1985GON/LAR 1985GON/LAR 1975MAT/NAS 1985GON/LAR 1994BLA/NOR 1994BLA/NOR 2000KRA/CIR 1997KIE/ZHA 1997KIE/ZHA 1997KIE/ZHA 1997WAY/CLA 1997KIE/ZHA 1997KIE/ZHA 1997KIE/ZHA 1997KIE/ZHA 2001ORL 2001ORL 2001MIR/KOS (continued)

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Table 29.3.1 (continued) Heats of Formation of C-Centered Radicals DfH0(R) C-Centered radicals %

CH2CH(NO2)2 CH2CH2C(NO2)3 % CH2N(NO2)CH2C(NO2)3 % CH2N(NO2)CH2CH(NO2)2 % CH2N(NO2)(CH2)2(NO2) NCH2C(NO2)3 % CH2N(NO2)(CH2)2(NO2) NCH2CH(NO2)2 (NO2)3CCH2N(NO2) CH2C%H–N(NO2)CH2C(NO2)3 (NO2)2CHCH2N(NO2) CH2C%H–N(NO2)CH2CH(NO2)2 % CH2CH2N(NO2)CH2C(NO2)3 % CH2CH2N(NO2)CH2CH(NO2)2 % CH2CH2ONO2 % CH2(ONO2)CHCH2ONO2 % CH(CH2ONO2)2 % CH2C(CH2ONO2)3 % CH2NHNO2 % CH2N(NO2)CH3 % CH2N(NO2)2 % CH2CH2N(NO2)CH3 % CH2N(NO2)CH2N(NO2)CH3 % CH2N(NO2)(CH2)N(NO2)CH3 CS C%(S)H % CH2SH % CH2SCH3 % CH2SPh % CH2SOCH3 HOC%(S)S % CH2SO2CH3 % CH2SO2Ph PhC%HSO2CH3 PhC%HSO2Ph Ph2C%SO2Ph Ph2C%SPh NC%(O) % CNH % CNO % CH2SiMe3 % CH2C(CH3)2SiMe3 % CP %

kcal/mol

kJ/mol

References

24.7 32.0 41.5 30.2 47.2

103.3 133.9 173.6 126.4 197.5

2001MIR/KOS 2001MIR/KOS 2001MIR/KOS 2001MIR/KOS 2001MIR/KOS

35.9

150.2

2001MIR/KOS

46.9

196.2

2001MIR/KOS

24.3

101.7

2001MIR/KOS

40.3 29.0 9.0 K6.1 K13.7 K37.8 39.4 35.7 50.3 34.5 48.3 41.4 67.0 71.8G2 36.3G2 32.7G1.4 64.2G3 5.7G3 26.4 K42.3G3 K13.7G3 K26.1G3 1.7G3 24.4G3 104.1G3 30.4 49.7G2.9 77.2G7.2 K7.6G1.5 K29.9 107.6G2.2

168.6 121.3 37.7 K25.5 K57.3 K158.2 164.8 149.4 210.5 144.3 202.1 173.2 280.3 300.4G8.4 151.9G8.4 136.8G5.9 268.6G12.6 23.8G12.6 110.5 K177.0G12.6 K57.3G12.6 K109.2G12.6 7G12.6 102G12.6 435.6G12.6 127.2 207.9G12.1 323G30 K32G6 K125 450G9

2001MIR/KOS 2001MIR/KOS 2001KOS/MIR 2001KOS/MIR 2001KOS/MIR 2001KOS/MIR 2001KOS/MIR 2001KOS/MIR 2001KOS/MIR 2001KOS/MIR 2001KOS/MIR 2001KOS/MIR 1998CHA 1994BER/ELL 1994BER/ELL 1994JEF/NIC 1993ZHA/BOR 1998BOR/LIU 1990MUR/LOV 1992BOR/HAR 1992BOR/HAR 1992ZHA/BOR 2001ORL/TUR 2001ORL/TUR 2001ORL/TUR 1996ZYR/DRO 2000WEN 2002SAI/PAL 1998BEC/WAL 1998BEC/WAL 1998CHA

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Heats of Formation of Atoms, Radicals, and Ions

1471

29.3.2 O-centered radicals Table 29.3.2 Heats of Formation of O-Centered Radicals DfH0(R) O-Centered radicals HO% FO% ClO% BrO% IO% HOO% FOO% ClOO% BrOO% IOO% OFO% OClO% ClOOClO% ClClO% NCO% CNO% HONNO% sym-ClO3 HSO% HSOO% CH3SOO% CF3SO2O% O3 NCO% O2NO% ONOO% HOS(O)2O% CH3O% CF3O% CCl3O% CH2ClO% CHCl2O% CH2aCH–O% CF3CHFO% C2H5O% CH3CHClO% CH3CCl2O% nC3H7O% iC3H7O% (CH3)2CClO% nC4H9O% sC4H9O%

kcal/mol 8.93G0.03 26G2.4 24.29G0.03 30.2G0.4 27.7G1.2 2.94G0.06 6.1G0.5 23.4G1 25.8G9.6 23G4 90.5G4.8 22.8 33.9G2.9 22G7 44.0 92.4 41.1 51.9G5 K5.2G0.5 26.8 18.2 K218 34.1G0.4 44.0 17.6G0.3 19.8 K122.3 5.0G0.5 K151.8G1.7 K9.1G2.2 K5.1G2.2 K7.7G2.2 4.4G0.3 K203.4 K3.3G0.8 K14.8G2.9 K21.9G2.8 K7.2G2.0 K11.6G0.8 K25.9G2.0 K15 K16.6

kJ/mol 37.36G0.13 109G10 101.63G0.1 126.2G1.7 115.9G5.0 12.30G0.25 25.4G2 98.0G4 108G40 96.6G15 378.6G20 95.4 142G12 90G30 184.1 386.6 172 217.2G21 K21.8G2.1 112 76 K912 142.7G1.7 184.0 73.7G1.4 82.8 K511.7 21.0G2.1 K635.1G7.1 K38.1G9.2 K21.3G9.2 K32.2G9.2 18.4G1.3 K851.0 K13.6G3.3 K61.9G12.1 K91.6G11.7 K30.1G8.4 K48.5G3.3 K108.4G8.4 K62.8 K69.5

References 2006RUS/PIN 2003NASA/JPL 2003NASA/JPL 2003NASA/JPL 2003NASA/JPL 2006RUS/PIN 1998CHA 1998CHA 1998CHA 2001IUPC 1998CHA 1994NIC/FRI 1989HAY/COX 1998CHA 1990TAK 2004JAN/ROS 2004POS/SHA 1992COL/SAN 2005DEN 1999ARM 1999ARM 1995TAK/PAS 1998CHA 1990TAK 1993DAV/KIM 1993DAV/KIM 2005FAT/KAS 2005RUS/BOG 2000REI/PRA 2001SUN/BOZ 2001SUN/BOZ 2001SUN/BOZ 2002SEB/BOC 2003WU/CAR 2005RUS/BOG 2001SUN/BOZ(b) 2001SUN/BOZ(b) 1973BEN/ONE 2002ERV/DET 2002SUN/BOZ 1974BAT/CHR 1974BAT/CHR (continued)

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Table 29.3.2 (continued) Heats of Formation of O-Centered Radicals DfH0(R) O-Centered radicals tC4H9O% CH2aCHCH2O% C6H5O% o-Cl–C6H4O% C6Cl5O% p-Cl–C6H4O% o-OH–C6H4O% p-OH–C6H4O% o-CH3O–C6H4O% p-CH3O–C6H4O% C6H2Cl3O%, 2,4,6trichlorophenoxyl C6H5CH2O% C10H7O%, naphthoxy-1 C10H7O%, naphthoxy-2 HC(O)O% FC(O)O% CH3C(O)O% CF3C(O)O% C6H5C(O)O% CF3OC(O)O% CH3OO% C2H3OO%, CH2a CHOO% C2H5OO% C3H5OO%, CH2a CHCH2OO% iC3H7OO% C4H7OO%, CH3CHa CHCH2OO% tC4H9OO% neo-C5H11OO% HOCH2OO% HOOCH2CH2OO% C6H5CH2OO% c-C6H7OO%, cyclohexadienyl c-C6H11OO% C6 H2 Cl3 O$3 , 4,6,7trichloro-2,3dioxabicyclo[2.2.2]octa-5,7-dien-1-yl c-C4H8NOO%, pyrrolidin-2-yl

kcal/mol

kJ/mol

References

K20.5G0.9 20.8 11.6G0.7 7.3 w15 w2.1 K44.5 K34.3 K30.0 K19.4 K6.6

K85.8G3.8 87.0 48.5G2.9 30.6 w63 w9 K186.3 K143.6 K125.5 K81.1 K27.5

2002ERV/DET 2002LEE/CHE 2005MUL/KOR 2003JAN/FAB 2000MUF/KHA 2000MUF/KHA 1991PON/TAK 1991PON/TAK 1991PON/TAK 1991PON/TAK 2003JAN/FAB

32.5G3 39.5 41.6 K31G3 K88 K43G3 K190.5 K12G4 K229G4 4.8G1.2 24.3G0.4

136.0G12.6 165.3 174.1 K129.7G12.6 368.0 K179.9G12.6 K797.0 K50.2G16.7 K958.1G16.7 20.1G5.1 101.7G1.7

2005FAT/KAS 1975MAH/DAR 1975MAH/DAR 1995KIM/BRA 1995TAK/PAS 2003BLA/ELL 1995TAK/PAS 2003BLA/ELL 2005PAC/ARG 2001BLA/RAM 2002SEB/BOC

K6.8G2.3 21.2

K28.5G9.6 88.7

2001BLA/RAM 2002LEE/CHE

K15.6G2.7 19.7G1.3

K65.4G11.3 82.6G5.3

1998KNY/SLA(b) 1998KNY/SLA

K24.3G2.2 K27.6 K38.7 K23.9 27.4G1 36.2G3

K101.5G9.2 K115.5 K162.1 100 114.6G4.2 151.6G12.6

1998KNY/SLA(b) 2004SUN/BOZ 1992LIG/COX 2002BOZ/SHE 1993ELM/MIN 2000KRA/CIR

K6G2.5 31.4

K25.0G10.5 131.4

2000KRA/CIR 2003JAN/FAB

24.2G3

101.3G12.6

2000KRA/CIR

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Heats of Formation of Atoms, Radicals, and Ions

(C2H5)N(CH3)CHOO% CF3OO% CF2ClOO% CFCl2OO% CH2ClOO% CHCl2OO% CCl3OO% CH3CHClOO% CH3CCl2OO% CH(O)CH2OO% CH3OCH2OO% CH3C(O)CH2OO% CH3C(O)OO% HOOO% CH3OOO% C2H5OOO% C4H7O–OO%, Ra tetrahydrofuran-2-yl C4H7O2–OO%, Ra dioxan-2-yl C6H2Cl3O%, 2,4,6trichlorophenoxy radical C6H4ClO%, ochlorophenoxy radical C6 H2 Cl3 O$2 , 2,4.6trichlorobicyclo-2,5hexadiene-1,4peroxyl-1phenoxy radical C12 H4 Cl5 O$2 , 2,4dichlorophenoxy1 0 ,3 0 ,5 0 -trichlorophenyl-6-2 0 ether radical C12 H5 Cl4 O$2 , 2,4dichlorophenoxy-1 0 ,3 0 -dichloro-phenyl 6,6 0 -ether radical

1473

K8.6G3 K151.8 K97.2G3.5 K51.1 K1.2G3.3 K4.6G2.7 K5.0G2.1 K13.1G0.8 K15.2G2.3 K20.5G1.0 K34.0G1.0 K34.0G1 K36.9G1.4 7.1G2 8G3 1.3G3 K36.3G4

K36.0G12.6 K635.0 K406.7G14.6 K213.7 K5.1G13.6 K19.2G11.2 K20.9G8.9 K54.7G3.4 K63.8G9.8 K85.9G4 K142.2G4.2 K142.1G4 K154.4G5.8 29.7G8.4 33.4G12.6 5.4G12.6 K152.0G16.7

2000KRA/CIR 2004JAN/ROS 1992LIG/COX 1992LIG/COX 1998KNY/SLA(b) 1998KNY/SLA(b) 1998KNY/SLA(b) 1998KNY/SLA(b) 1998KNY/SLA(b) 2006HAS/DEL 2000YAM/BOZ 2006HAS/DEL 2003NASA/JPL 2002DEN/KIE 1996JUN/SEI 1996JUN/SEI 2000KRA/CIR

K65.5G4

K274.0G16.7

2000KRA/CIR

K7.8G3

K32.6G12.6

2003BUR/KHA

4.3G1

18.0G4.2

2003BUR/KHA

30.7

128.4

2003BUR/KHA

K30.6G6

K128G25

2003BUR/KHA

K20.4

85.4

2003BUR/KHA

7366—CHAPTER 29—3/2/2007—18:03—CRCPAG—15385—XML MODEL B – pp. 1453–1485

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Comprehensive Handbook of Chemical Bond Energies

29.3.3 N-centered radicals Table 29.3.3 Heats of Formation of N-Centered Radicals DfH0(R) N-Centered Radicals ON NO2 N2O NH % NH2 % NNH % NCO % N3 % N2H3 (Z)-N2H2 NF % NF2 % NHF NBr HNO FNO ClNO BrNO INO NCO NCN NSi NH2C(O)N%H CH3C(O)N%H NH2C(S)N%H CH3C(S)N%H PhC(S)N%H HCON%H NH2C(NH)N%H % NHCN CH2N%H CH3N%H tBuN%H C6H5CH2N%H C6H5N%H (CH3)2N% (C6H5)(CH3)N% (C6H5)2N% 1-pyrrolyl 1-pyrazolyl Carbazol-9-yl CH3 N$2 C2 H5 N$2

kcal/mol 21.76G0.02 8.12G0.02 19.61G0.1 85.3G0.2 44.5G0.2 59.64 31.5 99.0G5 58.2 50.9G2.6 50 10.1G2 26.8G3.6 71.9G5 25.6G0.6 K15.7G0.4 12.36G0.10 19.63G0.2 26.8G5 28.9 111.1G0.7 89G15 0.2G3 K1.6G3 46.4G3 41.3G3 73.4G3 11.9G3 59.9G3 76.3G0.7 25.0G3 44.0G2 22.8G3 68.9G3 58.4G1 37.8G2 57.6G1.5 87.5G1.5 70.8G3 98.7G0.5 91.6G2 51.5G1.8 44.8G2.5

kJ/mol

References

91.04G0.08 33.97G0.08 82.05G0.4 357G1 186.2G1.0 249.5 131.8 414.2G20.9 243.5 213.0G10.9 209.2 42.3G8 112G15 301G21 107.1G2.5 K65.7G1.7 51.71G0.42 82.13G0.8 112.1G20.9 120.9 464.8G2.9 372G63 0.8G12.6 K6.7G12.6 194G12.6 173G12.6 307G12.6 49.8G12.6 250.6G12.6 319.2G2.9 104.6G12.6 184.1G8.4 95.4G12.6 288.3G12.6 244.3G4.2 158.2G4.2 241.0G6.3 366.0G6.3 269.2G12.6 413.0G2.1 383.3G8.4 215.5G7.5 187.4G10.5

2006RUS/PIN 2006RUS/PIN 1998CHA 1999AND 2005RUS/BOG 2000SMI/GOL 2000SMI/GOL 1998CHA 1988GRE/COL 1998CHA 1979HUB/HER 1998CHA 1989GUR/VEY 1998CHA 1999AND 1998CHA 1998CHA 1998CHA 1998CHA 2004JAN/ROS 1999BIS/CHO 1998CHA 1991BOR/JI(b) 1991BOR/JI(b) 2001ORL/TUR 2001ORL/TUR 2001ORL/TUR 1995BOR/ZHA 1991BOR/JI(b) 2001BIS/HOO 1988GRE/COL 1988COL 1998BOR/LIU 1998BOR/LIU 1997MAC/WAY 1988COL 1993BOR/ZHA 1997MAC/WAY 1991BOR/JI(b) 2006GIA/ICH 1992ARE/VEN 1987ACS/PET 1987ACS/PET

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Heats of Formation of Atoms, Radicals, and Ions

iC3 H7 N$2 nC4 H9 N$2 tC4 H9 N$2 (NO2)HN% (CH3)(NO2)N% (NO2)2N% CH3N%CH2N(NO2)CH3

34.9G2 33.6G2 23.3G2 38.8 33.2 47.8 44.3

1475

146.0G8.4 140.6G8.4 97.5G4.2 162.3 139.0 200.0 185.4

This book This book This book 2001KOS/MIR(b) 2001KOS/MIR(b) 2001KOS/MIR(b) 2001KOS/MIR(b)

29.3.4 S-centered radicals Table 29.3.4 Heats of Formation of S-Centered Radicals DfH0(R) S-Centered radicals SO SO2 SO3 S2O HOS% HC(O)S% HS%O2 HOS%O2 NCS% HS% CH3S% C2H5S% nC3H7S% iC3H7S% tC4H9S% C6H5S% C6Cl5S% C6H5CH2S% CH3S%O CH3S%O2 HSS% CH3SS% C2H5SS% iC3H7SS% tC4H9SS% HOC(S)S% HC(O)S% SF SF2 SF3

kcal/mol 1.2G0.3 K70.95G0.05 K94.6G0.17 K13.5G8 K1.6G0.5 13.5 K53 K92 71.7G2 34.2G0.2 29.8G0.4 24.1 19.1 17.9G2 10.5G2 58.0G1.1 w44 58.8 K16.0G2.4 K57.2 27.6G3.5 16.4G2 10.4G2 3.3G2 K4.6G2 26.4G1.1 13.5 3.1G1.5 K70.9G4 K120.2G8

kJ/mol 5.0G1.3 K296.84G0.21 K395.77G0.7 K56.5G33.5 K6.7G2.1 56.5 K221.8 K384.9 300G8 143.0G0.8 124.7G1.7 101 80 74.9G8.4 43.9G8.4 242.7G4.6 w184 246 K67G10 K239.3 115.5G14.6 68.6G8.4 43.5G8.4 13.8G8.4 K19.2G8.4 110.5G4.6 56.5 13.0G6.3 K296.7G16.7 K503.0G33.5

References 1998CHA 1998CHA 1998CHA 1998CHA 2005DEN 1990TAK 1980BOY/GUP 1984MAR 1999ARM 1996WIL/HOW 1994BER/ELL 1999ARM 1999ARM 1980JAN/REE 1980JAN/REE 2002SAN/MUR 2000MUF/KHA 2001ORL/TUR 2001IUPAC 1971SOL/BEN 1993OHA/DEP 1986HOW/GRI 1986HOW/GRI 1986HOW/GRI 1986HOW/GRI 1990MUR/LOV 1990TAK 1998CHA 1998CHA 1998CHA (continued)

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Table 29.3.4 (continued) Heats of Formation of S-Centered Radicals DfH0(R) S-Centered radicals SF4 SF5 ClS% SN SCl

kcal/mol

kJ/mol

K182.4G5 K210.3G3.6 37.4G4 63G25 37.4G4

K763.2G20.9 K879.9G15.1 156.5G16.7 263.6G105 156.5G16.7

References 1998CHA 1998CHA 1998CHA 1998CHA 1998CHA

29.3.5 Si, Ge-, Sn-, and Pb-centered radicals Table 29.3.5 Heats of Formation of Si-, Ge-, Sn-, and Pb-Centered Radicals DfH0(R) Si-, Ge-, Sn-, and Pb-Centered radicals SiF SiF2 % SiF3 SiCl SiCl2 % SiCl3 SiBr SiBr2 % SiBr3 SiI SiI2 % SiI3 SiH SiH2(1A1) SiH2(3B1) % SiH3 MeSi%H2 Me2Si%H Me3Si% % Si2H3 H3SiSi%H2 C6H5Si%H2 H3SiSi%H MeSi% MeSi%H Me2Si%% SiN

kcal/mol K11.2G2.1 K152.5G1.5 K235.9G4 37.0G1 K38.0G1.5 K76.0G1 48.7G2 K11.0G1 K38G2 75.0G10 22.1G2 8.4G15 90G2 65.2G0.5 86.2 47.9G0.6 33.7G1.5 18.6G1.5 3.6G1.6 w96 55.9G1.5 65.5 74.6G2 72.2 48.3G1.5 32.3G2 75G10

kJ/mol K46.9G8.8 K638G6 K987G20 154.8G4.2 K159.0G6.3 318G4.2 203.8G8.4 46.0G4.2 K159.0G8.4 313.8G42 92.5G8.4 35.3G63 376.6G8.4 273G2 360.7 200.4G2.5 141G6 78G6 15G7 w402 234G6 274 312G8 302.2 202G6 135G8 313.8G42

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References 1993FIS/KIC 1998BEC/WAL 1998BEC/WAL 2003HIL/LAU 2003HIL/LAU 2003HIL/LAU 2003HIL/LAU 2003HIL/LAU 2003HIL/LAU 1998CHA 1998BEC/WAL 1998CHA 1998CHA 1998BEC/WAL 1987BER/GRE 1994BER/ELL 1998BEC/WAL 1998BEC/WAL 1998BEC/WAL 1991RUS/BER(c) 1998BEC/WAL 1998BEC/WAL 1998BEC/WAL 2004JAN/ROS 1998BEC/WAL 1998BEC/WAL 1998CHA

Heats of Formation of Atoms, Radicals, and Ions

%

GeH3 GeF GeF2 % GeF3 GeCl GeCl2 % GeCl3 GeBr GeBr2 % GeBr3 GeI GeI2 % GeI3 SnF SnF2 % SnF3 SnCl SnCl2 % SnCl3 SnBr SnBr2 % SnBr3 SnI SnI2 % SnI3 % Sn(CH3)3 % Sn(C6H5)3 PbH PbF PbF2 % PbF3 PbCl PbCl2 % PbCl3 PbBr PbBr2 % PbBr3 PbI PbI2 % PbI3

53G2 K17.0G2.4 K137.2G4.8 K192.9G12 16.5G4.3 K40.9G1.2 K64.0G12 32.8G1.2 K14.6G1.2 K28.4G12 50.4G6 12.0G1 10G12 K22.7G1.7 K122.1G2.2 K154.6G12 8.3G2.9 K48.4G1.7 K69.8G12 18.2G2.9 K28.4G0.7 K38.0G12 41.3G2.9 K1.9G1 1.9G12 31.6 124G5 56.5G4.6 K19.2G2.5 K104G2 K117G14.3 3.6G12 K41.6G0.3 K42.5G19 16.9G10 K25.0G1.5 K24.9G19 25.7G9 K0.76G1 5.2G19

1477

221.8G8.4 K71G10 K574G20 K807G50 69G18 K171G5 K268G50 137G5 K61G5 K119G50 211G25 50.2G4 42G50 K95G7.2 K511G9.2 K647G50 35G12 K202.6G7.1 K292G50 76G12 K119G2.8 K159G50 173G12 K8.1G4.2 K8G50 132.2 518.8G21 236.2G19.2 K80.3G10.5 K435.1G8.4 K490G60 15.1G50 K174.1G1.3 K178G80 70.9G42 K104.4G6.3 K104G80 107.4G37.7 K3.2G4.2 22G80

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1994BER/ELL 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1991GUR/VEY 1998GAL/PAU 1992CAR 1998CHA 1998CHA 1998CHA 1991GUR/VEY 1998CHA 1998CHA 1991GUR/VEY 1998CHA 1998CHA 1991GUR/VEY 1998CHA 1998CHA 1991GUR/VEY

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29.4 Group additivity values for organic radicals The group additivity values (GAVs) are in 1976BEN, and updated GAVs are available in 1993COH/BEN, 1996COH, 1997BEN/COH. Table 29.4.1 GAVs of C/H Radicals GAVs C/H Radical groups

kcal/mol

kJ/mol

%

38.4 41.0 41.6 25.9 18.5 26.2 26.0 25.0 27.7 30.0 30.1 28.3 30.1 28.9 26.1 28.5 27.8 62.5 65.3 108.0 K10.0 K5.0 K2.4 0.5 8.6 10.2 27.3 5.5

160.7 171.5 174.1 108.4 77.4 109.6 108.8 104.6 115.9 125.5 125.9 118.4 125.9 120.9 109.2 119.2 116.3 261.5 273.2 451.9 K41.8 K20.9 K10.0 2.1 36.0 42.7 114.2 23.0

C–(C)(H)2 C–(C)2(H) % C–(C)3 % C–(Cd)(H)2 % C–(Cd)2(H) % C–(C)(Cd)(H) % C–(C)2(Cd) % C–(C)(Cd)2 % C–(CB)(H)2 % C–(C)(CB)(H) % C–(C)2(CB) % C–(CB)2(H) % C–(CB)2(C) % C–(CB)3 % C–(Ct)(H)2 % C–(C)(Ct)(H) % C–(C)2(Ct) % CB – % Cd–(H) % Ct– C–(%C)(H)3 C–(C)(%C)(H)2 C–(C)2(%C)(H) C–(C)3(%C) Cd–(%C)(H) Cd–(%C)(C) Ct–(%C) CB–(%C) %

References 1999COH 1999COH This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume 1999COH 1999COH 1999COH 1999COH 1999COH 1999COH 1999COH 1999COH

Table 29.4.2 GAVs of O/C/H Radicals GAVs O/C/H Radical groups %

C–(O)(H)2 C–(C)(O)(H) % C–(C)2(O) % C–(Cd)(O)(H) %

kcal/mol

kJ/mol

33.5 35.0 31.6 23.0

140.2 146.4 132.2 96.2

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References This volume This volume This volume 1999COH

Heats of Formation of Atoms, Radicals, and Ions

%

C–(Cd)2(O) C–(CB)2(O) % C–(CO)(H)2 % C–(C)(CO)(H) % O–(C) % O–(Cd) % O–(CB) % O–(CO) % O–(O) % CO–(H) % CO–(C) % CO–(Cd) % CO–(CB) % CO–(O) C–(%O)(H)3 C–(C)(%O)(H)2 C–(%C)(O)(H)2 C–(C)2(%O)(H) C–(C)(%C)(O)(H) C–(C)3(%O) C–(C)2(%C)(O) CB–(%O) Cd–(%O)(H) Cd–(%CO)(H) C–(%CO)(H)3 C–(C)(%CO)(H)2 CB–(%CO) O–(%C)(H) O–(%C)(C) O–(%O)(C) O–(%CO)(H) O–(%CO)(C) O–(%C)(CO) O–(O)(%O) O–(CO)(%O) O–(CB)(%O) CO–(%C)(H) CO–(%C)(C) CO–(CB)(%O) CO–(C)(%O) CO–(H)(%O) %

17.0 17.0 32.8 32.6 15.0 K10.8 K2.7 2.2 17.7 10 7.6 8.0 5.9 12.0 K10.0 K8.1 K8.1 K7.2 K7.2 K6.6 K6.6 K0.9 8.6 5.0 K10.0 K5.2 3.7 K37.9 K23.5 K4.5 K58.0 K43.1 K43.1 19.0 K19.0 K4.6 K29.4 K31.7 K34.4 K35.2 K32.1

1479

71.1 71.1 137.2 136.4 62.8 K45.2 K11.3 9.2 74.1 41.8 31.8 33.5 24.7 50.2 K41.8 K33.9 K33.9 K30.1 K30.1 K27.6 K27.6 K3.8 36.0 20.9 K41.8 K21.8 15.5 K158.6 K98.3 K18.8 K242.7 K180.3 K180.3 79.5 K79.5 K19.2 K123.0 K132.6 143.9 K147.3 K134.3

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This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume This volume 1999COH This volume 1999COH 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN 1999COH 1993COH/BEN 1993COH/BEN 1999COH 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN This volume 1993COH/BEN 1993COH/BEN This volume 1993COH/BEN 1993COH/BEN

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Table 29.4.3 GAVs of N/C/H/O Radicals GAVs N/C/H/O Radical groups %

N–(C)2 N–(C)(H) % N–(N)(H) % N–(CB)(H) % N–(C)(CB) C–(%N)(H)3 CB–(%N) N–(%N)(H)2 N–(%C)(H)2 N–(%C)(C)(H) N–(%C)(C)2 N–(%C)(C)(CB) % C–(N)(H)2 % C–(C)(N)(H) % C–(C)2(N) % C–(CN)(H)2 % C–(C)(CN)(H) % C–(C)2(CN) % C–(C)(CB)(CN) (CN)–(%C) (%NN)–(C) C–(%NN)(H)3 C–(C)(%NN)(H)2 C–(C)2(%NN)(H) C–(C)3(%NN) NO2–(%C) % C–(NO2)(H)2 % C–(NO2)(C)(H) % C–(NO2)(C)2 % C–(NO2)(CB)(H) %

kcal/mol

kJ/mol

57.8 54.0 46.8 42.5 51.7 K10.0 K0.5 11.4 4.8 9.0 24.4 26.2 31.5 33.6 31.9 60.4 64.2 65.5 44.4 3.0 61.5 K10.0 K6.7 K6.6 K8.2 K9.3 36.6 34.1 30.8 27.8

241.8 225.9 195.8 177.8 216.3 K41.8 K2.1 47.7 20.1 37.7 102.1 109.6 131.8 140.6 133.5 252.7 268.6 274.1 185.8 12.6 257.3 K41.8 K28.0 K27.6 K34.3 K38.9 153.1 142.7 128.9 116.3

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References This volume 1999COH 1999COH This volume This volume 1999COH 1999COH 1976BEN 1976BEN 1999COH 1976BEN 1976BEN This volume This volume This volume This volume This volume This volume 1999COH 1999COH 1999COH 1999COH 1999COH This volume This volume This volume This volume This volume This volume This volume

Heats of Formation of Atoms, Radicals, and Ions

1481

Table 29.4.4 GAVs of S/C/H/O Radicals GAVs S/C/H/O Radical groups %

S–(C) S–(CB) % SO2–(C) % S–(S) S–(%S)(H) S–(%S)(C) S–(%C)(H) S–(%C)(C) S–(%C)(CB) SO–(%C)(C) SO2–(%C)(C) SO2–(%C)(CB) % C–(S)(H) % C–(S)(H)2 % C–(SO)(H)2 % C–(SO2)(H)2 % C–(SO2)(CB)(H) % C–(SO2)(CB)2 % C–(S)(CB)2 %

kcal/mol

kJ/mol

References

39.5 41.6 K47.2 19.4 8.2 6.72 4.68 11.34 16.2 K14.4 K69.7 K72.3 71.8 31.5 30.1 38.6 33.8 34.1 28.5

165.3 174.1 K197.5 81.2 34.3 28.12 19.58 47.45 67.8 K60.2 K291.6 K302.5 300.4 131.8 125.9 161.5 141.4 142.7 119.2

This volume This volume This volume This volume This volume 1993COH/BEN 1993COH/BEN 1993COH/BEN 1993COH/BEN 1976BEN 1976BEN 1976BEN This volume This volume This volume This volume This volume This volume This volume

29.5 Enthalpy of formation of monoatomic cations Based on thermodynamics, the enthalpy of formation of monoatomic anions in gas-phase is given by Df H0 ðADÞZ Df H0 ðAÞDIEðAÞ Here DfH0(A) and IE(A) are the enthalpy of formation and the electron affinities of gaseous atoms, respectively. The following DfH0(AD) values are calculated using both Table 29.1 and the recommended IE(A) in 1996NIST. DfH 0(AC) A

kcal/mol

kJ/mol

Ac Ag Al Am Ar As Au

216.3 242.8G0.02 217.1G1.0 205.6 363.403G0.001 298.6G3.1 300.7G0.5

905 1015.9G0.8 908.4G4.0 860.4 1520.476G0.0.001 1249.5G13 1258.3G2.1 (continued)

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B Ba Be Bi Bk Br C Ca Cd Ce Cf Cl Cm Co Cr Cs Cu Dy Er Es Eu F Fe Ga Gd Ge H He Hf Hg Ho I In Ir K Kr La Li Lu Mg Mn Mo N Na Nb Nd Ne Ni Np

Comprehensive Handbook of Chemical Bond Energies

326.391G1.2 120.2G1.2 292.4G1.2 218.1G0.5 217.7G0.6 299.16G0.03 430.953G0.11 183.5G0.2 234.12G0.05 228.1G0.5 192.1G0.5 328.025G0.002 231.1 283.7 251.0G1.0 108.08G0.24 258.8G0.3 206.4G0.5 216.5G0.5 179.9G0.6 173.2G0.5 420.74G0.07 281.5G0.1 203.3 236.8G0.5 271.1G0.7 365.683G0.001 566.986 305.2G1.5 255.36G0.01 210.7G0.5 266.52G0.01 191.5G1 369.7G1 121.4G0.2 322.831 231.6G0.5 162.4G0.2 227.3G0.5 211.5G0.2 239.1G1.0 321.1G0.9 448.13G0.096 144.2G0.2 331.1G2 205.5G0.5 497.278 279.0G2.0 255.6

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1365.6G5 502.8G5.0 1223.5G5 912.5G2.1 911.0G2.4 1251.70G0.12 1803.108G0.45 767.6G0.8 979.54G0.20 954.5G2.1 803.8G2.0 1372.458G0.008 966.8 1187.1 1050.3G4.2 452.2G1.0 1082.9G1.2 863.4G2.1 905.7G2.1 752.6G2.4 724.5G2.1 1760.39G0.30 1177.9G1.3 850.79 990.9G2.1 1134.1G3 1530.017G0.006 2372.248 1276.9G6.3 1068.42G0.04 881.6G2.1 1115.13G0.04 801.3G4 1547.0G4 507.8G0.8 1350.725 969.1G2.1 679.5G1.0 951.1G2.1 884.8G0.8 1000.6G4.2 1343.3G3.8 1874.98G0.40 603.3G0.7 1385.1G8 860.0G2.1 2080.612 1167.2G8.4 1069.3

Heats of Formation of Atoms, Radicals, and Ions

O Os P Pa Pb Pd Pr Pt Pu Ra Rb Re Rh Rn Ru S Sb Sc Se Si Sm Sn Sr Ta Tb Tc Te Th Ti Tl Tm U V W Xe Y Yb Zn Zr

373.59G0.02 388.7G1.5 317.5G0.2 270.4 217.7G0.2 282.3G0.5 211.3G0.5 342.7G0.3 221.4G4.1 159.7 115.7G0.2 366.7G1.5 304.9G1 247.860 325.2G1.5 305.15G0.04 262.4G0.6 241.6G1 279.2G1 295.5G2 179.5G0.5 241.34G0.36 170.5G0.4 368.8G0.6 228.1G0.5 330 254.8G0.5 289.3G1.4 270.5G0.7 184.4G0.1 198.1G0.5 270.2G2 278.8G2 387.4G1.5 279.715 244.9G0.5 181.4G0.5 247.79G0.10 298.8G2.0

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1563.09G0.10 1626.4G6.3 1328.3G1.0 1131 910.8G0.8 1181.0G2.1 884.1G2.1 1434.0G1.3 926.4G17 668.3 483.9G0.8 1534.3G6.3 1275.7G4 1037.048 1360.8G6.3 1276.74G0.15 1098.0G2.5 1010.9G4 1168.1G4 1236.5G8 751.2G2.1 1009.8G1.5 713.5G1.7 1543.3G2.5 954.5G2.1 1380 1065.9G2.1 1210.6G6 1131.8G3 771.6G0.4 828.9G2.1 1130.6G8 1166.4G8 1620.9G6.3 1170.327 1024.5G2.1 759.0G2.1 1036.77G0.40 1250.1G8.4

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29.6 Enthalpy of formation of monoatomic anions Based on thermodynamics, the enthalpy of formation of monoatomic anions in gas-phase is given by Df H0 ðALÞZ Df H0 ðAÞLEAðAÞ Here DfH0(A) and EA(A) are the enthalpy of formation and the electron affinities of gaseous atoms, respectively. The following DfH0(AL) values are calculated using both Table 29.1 and the recommended EA(A) in 1996NIST. DfH 0(AK) A

kcal/mol

kJ/mol

Ag Al As Au B Ba Bi Br C Ca Ce Cl Co Cr Cs Cu F Fe Ga Ge H I In Ir K La Li Lu Mo Na Nb Ni O Os P Pb Pd

39.0G0.2 68.9G1.0 53.5G3.0 35.0G2.4 128.5G1.2 39.5G1.2 28.4G0.5 K50.8G0.03 142.186G0.11 41.9G0.2 78.4G0.8 K54.356G0.002 86.7 79.4G1.0 7.40G0.24 52.1G0.3 K58.56G0.07 92.4G4.6 55.1 60.5G0.7 34.711G0.001 K45.02G0.01 48.7G1 123.9G1 9.7G0.2 92.2G0.7 23.8G0.2 94.4G0.5 140.2G0.9 13.1G0.2 154.6G2 76.1G2 25.86G0.02 163.1G1.5 58.4G0.2 38.3G0.3 77.0G0.5

163.3G0.8 288.3G4.2 224.0G12.6 146.3G9.9 537.8G5.0 165.1G5.0 118.7G2.1 K212.6G0.12 594.905G0.460 175.5G0.8 327.9G3.3 K227.426G0.008 362.8 332.3G4.2 30.98G1.0 218.0G1.3 K245.02G0.30 386.5G19.3 230.5 253.0G3 145.232G0.006 K188.37G0.04 203.7G4.2 518.5G4.2 40.6G0.8 385.6G2.8 99.7G1.0 394.8G2.3 586.7G3.8 54.7G0.8 646.9G8.7 318.5G8.4 108.21G0.10 682.6G6.3 244.3G1.0 160.1G1.1 322.3G2.1

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Heats of Formation of Atoms, Radicals, and Ions Pt Rb Rh Ru S Sb Sc Se Si Sn Sr Ta Te Ti Tl Tm V W Y Zr

86.2G0.3 8.1G0.2 106.6G1 131.4G1.5 18.35G0.04 39.0G0.6 85.9G1.1 7.7G1 75.5G2 46.35G0.36 38.0G0.4 179.5G2.8 1.6G0.5 111.0G0.7 34.9G0.3 31.8G0.7 111.1G2 184.6G1.5 94.4G0.6 136.0G2.0

7366—CHAPTER 29—3/2/2007—18:04—CRCPAG—15385—XML MODEL B – pp. 1453–1485

1485 360.4G1.3 33.9G0.8 446.2G4.2 549.7G6.3 76.79G0.15 163.4G2.5 359.6G4.6 32.2G4.2 315.9G8.4 193.91G1.51 159.0G1.7 750.9G11.8 6.5G2.1 464.4G3 145.8G1.3 133.0G3.0 464.8G8.4 772.2G6.3 395.0G2.4 568.9G8.4

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1534 1988GLA 1988GON/GOM 1988GON/ZHA 1988GRA/PIM 1988GRE/COL 1988GRI/KAM 1988GUP/COL 1988GUS/AMI 1988HAN/BEA 1988HAN/WHI 1988HER 1988HER/LAR 1988HIL/LAU 1988HIR 1987HIR(b) 1988HIR/MIZ 1988HIR/MIZ(b) 1988HIR/NAK 1988HOL/LOS 1988HOL/LOS(b) 1988HUA/FRE 1988HUT 1988ILL 1988ISH/BRO 1988KAS/CHO 1988KEB/DIL 1988KEL/GEL 1988KIM/CHE 1988KLE 1988KOY/YAM 1988LAN/SQU 1988LAR/MCM 1988LAR/SZU 1988LAU/SCH 1988LEC/FRE 1988LEE/BYL 1988LES/BRU 1988LES/BRU(b) 1988LI/PIL 1988LIA/BAR 1988LOH/LIA 1988LOV/NES 1988LYM/HOL 1988MAT 1988MCD/DAV 1988MCL 1988MCM/HEI

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1620 2006HAS/DEL 2006HE/MOO 2006HER/SCH 2006HU/HEP 2006HU/ZHA 2006HUA/WEI 2006IMR/KOV 2006JAW/CEM 2006KIM/DOO 2006KOY/BOH 2006KRE/SCH 2006LAG/BAE 2006LAG/BAE(b) 2006LEM/WU 2006LER/KLE 2006LIN/MER 2006LOP/CAM 2006MAN/KEM 2006MIK/YOM 2006MOI/ARM 2006NIC/PAR 2006NUN/AGA 2006OZE/PED 2006OTT/CAM 2006PAO/SAS 2006PRA/BER 2006RAO/RED 2006ROD/GAY 2006ROU/FAR 2006RUS/PIN 2006SCH 2006SHA/AMO 2006SHI/FUJ 2006SKU/NIE 2006SRI/SU 2006TAN/LIU 2006TRO/USH 2006WAN/CRE 2006WAN/MOR 2006WIL/BEL 2006WU/STA 2006YAM/INO 2006YAN/ROD(b) 2006ZAI/ROS

Comprehensive Handbook of Chemical Bond Energies Hassouna, M., Delbos, E. et al., J. Phys. Chem. A, 110, 6667– 6672, 2006. He, L., Moon, Y. T. et. al., App. Phys. Lett., 88, 071901/1 – 071901/3, 2006. Herlert, A. and Schweikhard, L., Int. J. Mass Spectrom., 249/250, 215– 221, 2006. Hu, Q. J. and Hepburn, J. W., J. Chem. Phys., 124, 074311/1 – 074311/10, 2006. Hu, Q. J., Zhang, Q., and Hepburn, J. W., J. Chem. Phys., 124, 074310/1 – 074310/5, 2006. Huang, C. Q., Wei, L. X. et al., Acta Phys. Sinica., 55, 1083– 101088, 2006. Imrik, K. and Kovacs, G. et. al., J. Phys. Chem. A. 110, 6821– 6832, 2006. Jaworski, J. S. and Cembor, M., J. Phys. Org. Chem., 19, 276– 280, 2006. Kim, H., Dooley, K. S. et al., J. Chem. Phys. 124, 134304/1-134304/8, 2006. Koyanagi, G. K. and Bohme, D. K., J. Phys. Chem. A, 110, 1232 –1241, 2006. Kretzschmar, I., Schroder, D. et al., Int. J. Mass Spectrom., 249/250, 263– 278, 2006. Lago, A. F. and Baer, T., J. Phys. Chem. A, 110, 3036– 3041, 2006. Lago, A. F. and Baer., T. Int. J. Mass Spectrom., 252, 20 – 25, 2006. Lemoff, A. S., Wu, C. C. et al., J. Phys. Chem. A, 110, 3662– 3669, 2006. Lerch, D., Klein, A. et al., Phys. Rev. B, 73, 075430/1 – 07543430/11, 2006. Lind, J. and Merenyi, J., Phys. Chem. A, 110, 192– 197, 2006. Lopez, J. C., Caminati, W., and Alonso, J. L., Angew. Chem. Int. Ed., 45, 290– 293, 2006. Manard, M. J., Kemper, P. R., and Bowers, M. T., Int. J. Mass Spectrom., 249/250, 252– 262, 2006. Miksovska, J., Yom, J. et al., Biomacromolecules, 7, 476– 482, 2006. Moision, R. M. and Armentrout, P. B., J. Phys. Chem. A, 110, 3933– 3946, 2006. Nicovich, J. M., Parthasarathy, S. et al., J. Phys. Chem. A, 110, 6874– 6885, 2006. Nunes, P. M., Agapito, F. et al, J. Phys. Chem. A, 110, 5130– 5134, 2006. Ozensoy, E., Peden, C. H. F., and Szanyi, J., J. Phys. Chem. B, 110, 8025– 8034, 2006. Ottaviani, P., Caminati, W. et al., Chem. Eur. J., 12, 915– 920, 2006. Paolantoni, M., Sassi, P. et al., J. Raman Spectrosc., 37, 528– 537, 2006. Pratte, P., van den Bergh, H., and Rossi, M. J., J. Phys. Chem. A, 110, 3042– 3058, 2006. Rao, P. S., Reddy, R. R., and Potukuchi, D. M., J. Quant. Spectroc. Radiative Transfer, 98, 81 – 84, 2006. Rodriguez, L. M. and Gayone, J. E. et al., J. Phys. Chem. B, 110, 7095– 7097, 2006. Roura, P., Farjas, J. et al., Phys. Rev. B, 73, 085203/1 – 085203/15, 2006. Ruscic, B., Pinzon, R. E. et al, J. Phys. Chem. A, 110, 6592– 6601, 2006. Schofield, K., J. Phys. Chem. A, 110, 6938– 6947, 2006. Shanks, D., Amorati, R., et al., J. Org. Chem., 71, 1033– 1038, 2006. Shibasaki, K., Fujii, A. et al., J. Phys. Chem. A, 110, 4397– 4404, 2006. Skulan, A. J., Nielsen, I. M. B. et al., J. Phys. Chem. A, 110, 281– 290, 2006. Srinivasan, N. K., Su, M. C. et al., J. Phys. Chem. A, 110, 6602– 6607, 2006. Tan, L., Liu, F., and Armentrout, P. B., J. Chem. Phys., 124, 084302/1 – 084302/14, 2006. Troe, J., Ushakov, V. G., and Viggiano, A. A., J. Phys. Chem. A, 110, 1491– 1499, 2006. Wang, G. T. and Creighton, J. R., J. Phys. Chem. A, 110, 1094– 1099, 2006. Wang, G., Morikawa, Y. et al., J. Phys. Chem. B, 110, 9– 11, 2006. Wilson, K. R., Belau, L. et al., Int. J. Mass Spectrom., 249/250, 155– 161, 2006. Wu, G. and Stace, A. J., Int. J. Mass Spectrom., 249/250, 289– 295, 2006. Yamaji, M., Inomata, S. et al., Chem. Phys. Lett., 417, 211 –216, 2006. Yang, Z. and Rodgers, M. T., J. Phys. Chem. A, 110, 1455– 1468, 2006. Zaitsev, V., Rosokha, S. V., et al., J. Org. Chem., 71, 520–526, 2006.

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Index of compound classes A Ac-containing species, 643 Acid anhydrides RC(O)O(O)R 0 C–H bonds aliphatic, 96–97 aromatic, 97 cyclic, 99 N-containing, 119–121 Si-containing, 100 C–O bonds, 335 –336 Acid (or acyl) halides RC(O)X C–Br bonds, 241, 242 C–C bonds, 181 –183 C–Cl bonds, 229 C–F bonds, 216 C–H bonds, 85 C–I bonds, 252 Ag-containing species AgC clusters, 999–1008 AgK clusters, 1009 neutrals, 990 –999 Al-containing species neutrals, 1052–1062 AlC clusters, 1062– 1067 Alcohols ROH C–C bonds aliphatic, 178–180 aromatic, 179 diols, 180 NH2-containing, 180 C–H bonds aliphatic, 70 arenes, 71– 72 aromatic, 72 –73 cyclic, 72 diols, 73 N-containing, 118 O –C bonds aliphatic, 321–322 aromatic, 324 cyclic, 323

halides, 321 heterocyclic, 324 polyols, 324 unsaturated, 321 O –H bonds aliphatic, 256–258 armatic, 259,260 cyclic, 259 diols, 260 enols, 260 Si-containing, 261 tropolone, 260 unsaturated, 256 Aldehydes RC(O)H C –C bonds aliphatic, 181, 182 armatic, 183 ethanal, 181 unsaturated, 182 C –H bonds aliphatic, 83 armatic, 84 cyclic, 84 furfurol, 84 halides, 83 unsaturated, 85 Alkanes C –C bonds chain, 147–153 cyclic, 153 –154 C –H bonds chain, 8, 19– 23 cyclic, 31– 39 Alkenes C –C bonds chain, 154, 156 –160 cyclic, 160 –161 C –H bonds chain, 25–30 cyclic, 31– 39 Alkynes C –C bonds, 154–156

1621

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1622 C– H bonds, 24–25 Am-containing species AmC clusters, 664 –665 neutrals, 664 Amides RC(O)NR2 0 C– H bonds, 119 C– N bonds, 414, 417 –418 sarcosines, 419 N–H bonds aliphatic, 373 amidines, 375 aromatic, 374 carboxamides, 375 O-containing, 374 S-containing, 372, 374 N–N bonds, 399 O –H bonds benzamides, 276 carboxamides, 276 Amines RNR2 0 , see also Anilines C– C bonds aliphatic, 197 aromatic, 196 CO-containing, 199 di-, 198 nitrozoamines, 200 O-containing, 199 C– H bonds aliphatic, 102–104 armatic, 104– 105 aza-containing, 102, 112 CO-containing, 119 cyclic, 121–125 NO2-containing, 110 O-containing, 118 C– N bonds aliphatic, 411–413 aromatic, 413 cyclic, 413 pyridines, 413 N–H bonds aliphatic, 370 anilines, 9, 378 aromatic, 371 hydrazines, 371 S-containing, 372 Si-containing, 377 N–N bonds aromatic, 397 halides, 397 N-containing, 396, 397 NO2-containing, 280 P-containing, 400 SO2-containing, 400 N–O bonds, 352 Anhydrides, see Acid anhydrides Anilines, also see Amines ArNR2 0 C– H bonds, 105 N–H bonds mono-substituted, 378 –379 polysubstituted, 379–380

Comprehensive Handbook of Chemical Bond Energies Antimony cluster/complexes anions, 1240 cations, 1240 neutrals, 1239 Aromatic compounds ArH C–C bonds anthracenes, 165 benzenes, 161 –165 cyclic, 164, 165, 166 indenes, 165 naphthalenes, 164 phenanthrenes, 165 tetralins, 166 C–H bonds acenaphthenes, 56 anthracenes, 51, 52, 58, 61 arenes, 40–47 benzanthrenes, 59 benzofluorences, 59 chrysenes, 60 dihydroacridenes, 53 dodecahedrane, 61 fluorenes, 101, 116, 117, 125 indanes, 47 indenes, 47 naphthalenes, 49–50 phenalenes, 59 phenathrenes, 51 poly-ring, 48–61 pyrenes, 61 tetralins, 48 thioxantheces, 53 triphenylenes, 30, 59, 131 xantheces, 52–53 Arsenic clusters/complexes anions, 1239 cations, 1238–1239 neutrals, 1238 As-containing compounds As–As bonds, 487 As–H bonds, 487 As–halogen bonds, 487–488 As–N bonds, 488 As–O bonds, 488 As–P bonds, 488 As–S bonds, 488 As–Sb bonds, 488 As–Se bonds, 488 Astatine clusters/complexes anions, 1427 cations, 1427 neutrals, 1427 Au-containing species AuC clusters, 1021–1025 AuK clusters, 1025–1026 neutrals, 1009– 1021 Azacyclic compounds C–H bonds, 113, 124 Azides or hydrazines R2NNR2 0 C–H bonds, 112 C–N bonds

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Index of Compound Classes alkyl, 416 aromatic, 417 halides, 416 N–H bonds, 369, 371, 374, 377 N–N bonds aliphatic, 397 aromatic, 397 halides, 397

B B-containing species BC clusters, 1049–1051 BK clusters, 1051 neutrals, 1041–1048 Ba-containing species BaC clusters, 598–599 neutrals, 596 –597 Be-containing species BeC clusters, 573–574 BeK clusters, 574 neutrals, 571 –573 Bi-containing compounds Bi–Bi bonds, 491 Bi–H bonds, 490 Bi–halogen bonds, 491 Bi–O bonds, 491 Bi–P bonds, 492 Bi–Pb bonds, 492 Bi–S bonds, 491 Bi–Sb bonds, 492 Bi–Se bonds, 491 Bi–Te bonds, 492 Bi–Tl bonds, 492 Bismuth clusters/complexes anions, 1241 cations, 1241 neutrals, 1240 Bk-containing species, 665 Bromides RBr C–Br bonds, 164–169 C(O)-containing, 241–242 C(O)O-containing, 242 cyanogen, 233 halogened alkanes, 233–239 halogened alkenes, 236–237, 238 halogened alkynes, 235 halogened aromatics, 240–241 halogened cyclics, 239– 240 halogened radicals, 243 NO2-containing, 243 C–C bonds aromatic, 176 CO-containing, 183 –187 saturated, 168 –175 C–H bonds As-containing, 133 N-containing, 105, 117, 119 O-containing, 87 P-containing, 132

1623 saturated, 63, 64, 67 S-containing, 131 Se-containing, 133 Te-containing, 133 unsaturated, 69 O –Br bonds, 367 O –H bonds bromo-hydroperoxide, 267 hypobromous acid, 256 N–Br bonds, 423 N–H bonds, 371 S– Br bonds, 448–449 Bromine clusters/complexes anions, 1402– 1413 cations, 1401–1402 neutrals, 1399–1401

C Ca-containing species CaC clusters, 587 –591 neutrals, 584–587 Carbon clusters C –C bonds, 205–207 Carbon clusters/complexes anions, 1136–1140 cations, 1099–1135 neutrals, 1087–1097 Carboxylic acids RC(O)OH C –Br bonds, 242 C –C bonds aliphatic, 187 amino acids, 187, 189, 190 aromatic, 188 OH-containing, 189 oxalic acids, 189 prolines, 190 sarcosines, 189 unsaturated, 187 C –Cl bonds, 229–230 C –H bonds aliphatic, 93–94 aromatic, 94 cyclic, 94 glycolic, 94 O-containing, 94 C –I bonds, 252 O –C bonds aliphatic, 333–334 aromatic, 334, 335 glycolic, 335 unsaturated, 334 O –H bonds aliphatic, 262–263 aromatic, 264 nicotinic acid, 265 pyridium, 265 Cd-containing species CdC clusters, 1035–1036 neutrals, 1033–1035

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1624 Ce-containing species CeC clusters, 618 –619 neutrals, 617–618 Cf-containing species, 665 Chlorides RCl C– C bonds aromatic, 176–177 O-containing, 181, 182 saturated, 168 –175 unsaturated, 166–167 C– Cl bonds C(O)-containing, 229 C(O)N-containing, 230, 231 C(O)O-containing, 229, 230 CN-containing, 228, 229 cyanogen, 218 halogened alkanes, 218– 225 halogened alkenes, 220– 225 halogened alkynes, 200 halogened aromatics, 226–228 halogened cyclics, 226, 228 halogened radicals, 232– 233 N-containing, 231, 232 NO2-containing, 230 S-containing, 231 C– H bonds N-containing, 108, 117 O-containing, 85 saturated, 60 –67 unsaturated, 67–68 N–Cl bonds, 422–423 O –Cl bonds, 366 –367 O –H bonds chloro-hydroperoxide, 266, 267 chloro-ol, 256 hypochlorous acid, 256 S–Cl bonds, 447–448 Chlorine clusters/complexes anions, 1379–1399 cations, 1377–1378 neutrals, 1374–1377 Cm-containing species, 665 Co-containing species C– C bonds, 203 CoC clusters, 868–881 CoK clusters, 881–882 Co– C bonds, 11 Co– X bonds, 855 –868 Cr-containing species CrC clusters, 723–732 CrK clusters, 733–734 neutrals, 713–723 Cs-containing species CsC clusters, 565–568 CsK clusters, 569 neutrals, 563–564 Cu-containing species CuC clusters, 982–988 CuK clusters, 989 neutrals, 967–981 Cyanides RCN, see Nitriles

Comprehensive Handbook of Chemical Bond Energies Cyclic hydrocarbons C–C bonds, 196–197 C–H bonds, 31 –39

D Dy-containing species DyC clusters, 634 neutrals, 631–634

E Er-containing species ErC clusters, 637 neutrals, 636–637 Es-containing species, 665 Esters RC(O)OR 0 C–Br bonds, 242, 243 C–C bonds aliphatic, 183 aromatic, 190 N-containing, 190 oxalates, 190 polycyclic, 191 unsaturated, 189 C–Cl bonds, 230 C–H bonds aliphatic, 96– 97 aminoacetates, 120 aromatic, 97 CN-containing, 121 cyclic, 100 dioates, 98 diones, 97–99 fluorenes, 101 N-containing, 120 oxalic, 97 Si-containing, 100 C–I bonds, 252 O–C bonds aliphatic, 335 aromatic, 336 halogened, 335 unsaturated, 335 O–O bonds, 316 –318 Ethers ROR 0 C–C bonds aliphatic, 180 aromatic, 181 cyclic, 181 furans, 181 C–H bonds aliphatic, 73– 74, 76–77 aromatic, 8, 75 cyclic, 77 –83 dialkyloxy, 76– 77 furans, 78 halides, 73 oxiranes, 77 pyrans, 79, 82, 127 O–C bonds

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Index of Compound Classes aliphatic, 325–329 anisoles, 8, 329 aromatic, 329 –331 halides, 2325 heterocyclic, 332 tropylium, 332 unsaturated, 325, 326 Eu-containing species EuC clusters, 628 neutrals, 626 –627

F Fe-containing species FeC clusters, 815 –838 FeK clusters, 838 –839 neutrals, 803 –814 Fluorides RF C–C bonds aromatic, 176, 177 CO-containing, 185 C(O)O-containing, 189 saturated, 168 –176 unsaturated, 166, 167 C–F bonds C(O)-containing, 216 C60, 216 C70, 216 cyanogen, 211 halogened alkanes, 211–215 halogened alkenes, 214–215 halogened alkynes, 213, 214 halogened aromatics, 215, 216 halogened cyclics, 215 halogened radicals, 217 NO2-containing, 216 C–H bonds aromatic, 69 O-containing, 83, 85 saturated, 60– 67 unsaturated, 67–69 N–F bonds, 422 O –F bonds, 365 O –H bonds fluo-hydroperoxides, 266, 267 fluoro-acid, 262 fluoro-ol, 256, 257 hypofluorous acid, 255 S–F bonds, 446 Fluorine clusters/complexes anions, 1355–1374 cations, 1355 neutrals, 1351–1354 Fm-containing species, 665

G Ga-containing species GaC clusters, 107 GaK clusters, 1075

1625 neutrals, 1068–1073 Gd-containing species GdC clusters, 629–630 neutrals, 628–629 Ge-containing compounds Ge–Br bonds, 471 Ge–C bonds, 471 Ge–Cl bonds, 470 Ge–F bonds, 470 Ge–Ge bonds, 469–470 Ge–H bonds, 467–469 Ge–I bonds, 471 Ge–O bonds, 472 Ge–S bonds, 473 Ge–Se bonds, 473 Ge–Si bonds, 472 Ge–Sn bonds, 472 Ge–Te bonds, 473 O –O bonds, 315 Germanium neutral complexes anions, 1156 cations, 1155– 1156 neutrals, 1153–1155

H Halides, also see Acid halides C –Br bonds, 233– 243 C –C bonds, 166–178 C –Cl bonds, 218–233 C –F bonds, 212–217 C –H bonds, 74 C –I bonds, 243– 253 C –S bonds, 421 N–Br bonds, 423 N–C bonds, 406, 407, 411 N–Cl bonds, 422– 423 N–F bonds, 422 N–H bonds, 369 N–I bonds, 423–424 N–N bonds, 397 N–O bonds, 48,351 N–S bonds, 421 O –Br bonds, 367 O –C bonds, 321, 323, 325, 338, 339, 342 O –Cl bonds, 366–367 O –F bonds, 365 O –H bonds, 255 –256 O –I bonds, 368 O –O bonds, 311, 313, 315–319 S– Br bonds, 448–449 S– Cl bonds, 447 –448 S– F bonds, 445–446 S– H bonds, 428 S– I bonds, 449 S– P bonds, 449–450 Heterocyclic compounds C –C bonds furans, 181 oxiranes, 191

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1626 piperidines, 197 prolines, 191 pyridines, 196 C– H bonds acridines, 53, 117 As-containing, 132 dioxepane, 82 furans, 78 isochromanone, 11 morpholines, 122 oxathiolane, 129 oxazolidines, 122–123 oxiranes, 77 P-containing, 132 piperazines, 125 piperidines, 113 pyran, 79, 82 pyrazine, 113, 115–116 pyrimidines, 114, 125 pyrroles, 112 pyrrolidines, 112 quinlines, 115 quinuclidines, 112 thianes, 127– 128 d-valerolactone, 100 3-caprolactone, 100 C– I bonds, 253 C– N bonds, 411 N–C bonds furans, 441 N–H bonds adenines, 392 azepines, 393 aziridines, 387 azolidines, 389 azolines, 394 carbazoles, 392 hydantoins, 388 imidazoles, 388 imidazolines, 395 iminostibenes, 393 indoles, 391 phenothiazines, 393 phenothioazines, 393 phthalazines, 392 phthalimides, 391 piperidones, 390 pyrazolidines, 389 pyridazines, 391 pyridines, 389 pyridones, 390 pyrimidines, 395 pyrroles, 387 pyrrolidones, 387 quinolines, 392 quinolones, 392 succinimides, 388 tetrazines, 394 uracil, 376 uzazoles, 389 N–halogen bonds, 423, 425

Comprehensive Handbook of Chemical Bond Energies O–C bonds, 332, 333, 334, 345 O–H bonds imidazoles, 278, 279, 280 piperidines, 277 pyrroles, 277 pyrrolidines, 277, 278 O–N bonds furazans, 355, 357 furoxans, 359 peridines, 354 phenazines, 358 Hf-containing species HfC clusters, 686–687 neutrals, 685–686 Hg-containing species HgC clusters, 1039–1040 neutrals, 1036– 1039 Ho-containing species HoC clusters, 635–636 neutrals, 634–635 Hydrocarbon radicals C–C bonds alphatic, 207 aromatic, 208 C clusters, 205 –207 halogened, 208 unsaturated, 207 C–H bonds alphatic, 134 –135 aromatic, 139 cyclic, 137 –139 unsaturated, 136 –137 Hydrogen clusters, 494–496 molecules, 493 Hydroperoxides and Peroxides, ROOR 0 O–C bonds aliphatic, 337, 338 armatic, 340 cyclic, 338, 341 halides, 338, 339 O–H bonds aliphatic, 266– 268 aromatic, 269 CN-containing, 270 CN-containing, 270 CO-containing, 270 C(O)O-containing, 270 cyclic, 268, 271 OH-containing, 269 O–N bonds, 344, 351– 352 O–O bonds aliphatic, 310– 312 armatic, 314, 315 artemisinin, 320 cyclic, 318 flavins, 320 halides, 311, 313, 315 –319 P-containing, 319 pernitric acid, 219 peroxycarboxylic, 312

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Index of Compound Classes

1627 aromatic, 87–90 cyclic, 91– 92 diones, 90 ketenes, 85 N-compounds, 89, 119, 124 C –I bonds, 252 N–H bonds amides, 373 urea, 372

poly-cyclic, 320 S-containing, 315, 319 trioxides, 315 O –S bonds, 364

I In-containing species InC clusters, 1083 neutrals, 1075–1082 Iodides RI C–C bonds CO-containing, 184 saturated, 168, 172 C–H bonds, 64 C–I bonds C(O)-containing, 252 C(O)O-containing, 252 CN-containing, 252 cyanogen, 243 halogened alkanes, 244–249 halogened alkenes, 247, 248, 249 halogened alkynes, 248 halogened aromatics, 255–252 halogened cyclics, 250 halogened radicals, 253 N-containing, 253 NO2-containing, 253 O-containing, 252 N–I bonds, 423 –424 O –I bonds, 368 S–I bonds, 449 Iodine clusters/complexes anions, 1417–1426 cations, 1416 neutrals, 1414–1415 Ir-containing species IrC clusters, 901–902 neutrals, 859 –901 Isocyanides RNC C–N bonds, 405

L La-containing species LaC clusters, 614 –616 neutrals, 612–613 Lead neutral complexes anions, 1161 cations, 1159– 1161 neutrals, 1159 Li-containing species LiC clusters, 500– 516 neutrals, 496–500 Lr-containing species, 665 Lu-containing species LuC clusters, 642 neutrals, 640–641

M Md-containing species, 665 Mg-containing species MgC clusters, 579 –584 neutrals, 574–579 Mn-containing species MnC clusters, 787–793 MnK clusters, 793–794 neutrals, 781–787 Mo-containing species MoC clusters, 746–750 MoK clusters, 751 neutrals, 734–746

K

N

K-containing species KC clusters, 544–556 KK clusters, 557 neutrals, 541 –544 Ketones RC(O)R 0 C–Br bonds, 242 C–C bonds aliphatic, 183–184 aromatic, 185 –186 diketenes, 186 diones, 186 halides, 183, 184, 185 C–Cl bonds, 229 C–F bonds, 216 C–H bonds aliphatic, 85–87

N oxides R’’R’RNO N–N bonds, 399 O –N bonds alkyls, 353 azoxys, 357 benzofurazans, 356 benzonitriles, 355 benzylidenes, 356 di-N-oxides, 357 furazans, 357 furoxans, 54 furoxans, 359 phenazines, 358 polycyclic, 355 pyridines, 354 quinolines, 358

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1628 Na-containing species NaC clusters, 522–540 NaK clusters, 541 neutrals, 516–521 Nb-containing species NbC clusters, 704–708 neutrals, 700–703 Nd-containing species NdC clusters, 622–623 neutrals, 621–622 Ni-containing species neutrals, 903–920 NiC clusters, 921 –930 NiK clusters, 931 Nitrides NX or NM N–H bonds, 369 Nitriles RCN and Isocyanides RNC C– Br bonds, 236 C– C bonds aliphatic, 192–193 aromatic, 193, 194, 195 cyanides, 192 –195 cyanogen, 191 cyclic, 193 dinitriles, 195 O-containing, 199 unsaturated, 192, 193 C– Cl bonds, 220 C– H bonds aliphatic, 106 aromatic, 41, 44, 106 isocyanides, 108 N-containing, 108 O-containing, 108 C– I bonds, 252 N–C bonds azides, 404 iso-, 405 N–H bonds, 370, 372 O –C bonds, 345 S–C bonds, 443 Nitro-compounds RNO2, RNO C– C bonds aliphatic, 200 CN-containing, 201 di-nittro-, 200, 201 hexa-nitro-, 202 NH-containing, 202 nitrozoamines, 202 penta-nitro-, 202 tetra-nitro-, 202 tri-nitro-, 201 C– H bonds aliphatic, 109–110 aromatic, 111 aza-, 111 cyclic, 110 NH-containing, 110 O-containing, 112 C– O bonds, 342–345 N–Br bonds, 423

Comprehensive Handbook of Chemical Bond Energies N– C bonds aliphatic, 406– 408 aromatic, 407–409 cyclic, 408 furans, 411 halides, 406 poly-nitro, 409 –411 unsaturated, 407 N– Cl bonds, 422 N– F bonds, 422 N– N bonds amines, 398 azepines, 401 benzoazepines, 401 carbazoles, 401 indoles, 401 phenoxazines, 402 soindoles, 401 N– I bonds, 423 N– S bonds, 420 O–H bonds hyponitrite, 261 isocyanic acid, 261 nitric acid, 261 nitrous acid, 260 O–N bonds alkyl, 349 –350 amines, 352 armatic, 350, 352 halides, 348–351 heterocyclic, 354, 355, 357 imino-, 352 nitroso-compounds, 352 peracid, 351 peroxy, 351 sulfate, 352 unsaturated, 352 Nitrogen clusters/complexes anions, 1219–1234 cations, 1171 –1219 neutrals, 1163–1171 Nitrosothio N– S bonds, 420 No-containing species, 665 Np-containing species neutrals, 662 NpC clusters, 662–663

O organomecury species O–H bonds, 285 Os-containing species neutrals, 851–852 OsC clusters, 853 Oxides OX or OM O–H bonds, 255 Oximes R2CN ZOH and Hydroxylamines R2NOH O–H bonds aliphatic, 272

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Index of Compound Classes amines, 277 aromatic, 274 azacyclic, 282 bicyclic, 282–283 cyclic, 277–284 fluorenic, 274 hydroxamic acid, 275 imidazoles, 278 indolinol, 283, 284 perrolidines, 278 phenanthridine, 284 phthalimides, 283 piperdines, 281, 284 piperidines, 281 pyrimidines, 281 pyrroles, 277 quinolines, 284 Oxygen neutral complexes anions, 1300–1322 cations, 1259–1299 neutrals, 1243–1258

P P-containing compounds N–H bonds, 383 O –H bonds metaphosphoric acid, 261 O –O bonds, 319 P –Bi bonds, 487 P –Br bonds, 483 P –Cl bonds, 483 P –F bonds, 483 P –H bonds, 481 P –I bonds, 483 P –N bonds, 484 P –O bonds, 484–485 P –P bonds, 482 P –S bonds, 485 –486 P –Sb bonds, 487 P –Se bonds, 486 P –Si bonds, 484 P –Te bonds, 486 P –Tl bonds, 486 Pa-containing species neutrals, 651 PaC clusters, 651 Pb-containing compounds Pb–Bi bonds, 480 Pb–Br bonds, 479 Pb–C bonds, 478 Pb–Cl bonds, 479 Pb–F bonds, 479 Pb–H bonds, 478 Pb–I bonds, 479 Pb–O bonds, 480 Pb–Pb bonds, 478 Pb–S bonds, 480 Pb–Se bonds, 480 Pb–Sn bonds, 479

1629 Pb –Te bonds, 480 Pd-containing species neutrals, 932–939 PdC clusters, 939–940 PdK clusters, 941 Peroxides, see Hydroperoxides Peroxys ROO and Trioxides ROOO O –Br bonds, 367 O –C bonds aliphatic, 338–340 aromatic, 340 CO-containing, 341 cyclic, 340 halides, 339 N-containing, 341 OH-containing, 341 unsaturated, 339, 340 O –Cl bonds, 366 O –F bonds, 365 O –I bonds, 368 O –O bonds, 315– 316 Phones ArOH O –H bonds bi-, 292 chromenes, 294 di-substituted, 289–290 free radicals, 308– 309 galvinols, 304 indophenol, 302 metal-containing, 306 –308 mono-substituted, 285–289 penta-substituted, 292 poly-rings, 295–297 pyrimidinols, 293 S-containing, 302 sterical, 298– 299 stilbenes, 304 tetra-substituted, 291 tocopherols, 9, 294 tri-substituted, 290–291 ubiquinols, 295 Phosphorus ions anions, 1236– 1237 cations, 1235–1236 Pm-containing species neutrals, 623 PmC clusters, 623 Po-containing compounds Po–Po bonds, 454 Polysulfides RSSR 0 , RSnR 0 and RSS O –H bonds, 302 S– C bonds, 441 –442 radicals, 444 S– H bonds, 430–431 S– S bonds, 433– 435 Pr-containing species neutrals, 619–620 PrC clusters, 620 –621 Pt-containing species neutrals, 941–962 PtC clusters, 963– 965

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1630 PtK clusters, 965–966 Pu-containing species neutrals, 663–664 PuC clusters, 664

R Ra-containing species, 599 Radicals As –H bonds, 487 As –halogen bonds, 487 –488 Bi–H bonds, 490 Bi–halogen bonds, 491 C– C bonds alkenyls, 207 alkyls, 207–208 alkynyls, 207 aromatic, 208 C– H bonds alkenyls, 136–137 alkyls, 134–135 alkynyls, 136–137 aromatic, 139 C(O)-containing, 144 cyclic, 137–139 halogened, 138–143 N-containing, 144 O-centred, 143–144 P-containing, 145 S-containing, 145 C(O)-containing, 209 clusters, 205 –207 halogened, 209 N-centered, 210 O-containing, 209– 210 S-centered, 210 Ge–Br bonds, 471 Ge–Cl bonds, 470 Ge–F bonds, 470 Ge–H bonds, 467 Ge–I bonds, 471 N–C bonds, 419 N–H bonds, 369, 370, 378 O –C bonds, 346–347 O –H bonds, 308– 309 O –N bonds, 353 O –S bonds, 364 P –Br bonds, 483 P –Cl bonds, 483 P –F bonds, 483 P –H bonds, 481 Pb–Br bonds, 479 Pb–Cl bonds, 479 Pb–F bonds, 479 Pb–H bonds, 478 Pb–I bonds, 479 S–Br bonds, 448 S–C bonds, 436, 442, 444 S–Cl bonds, 447 S–F bonds, 446

Comprehensive Handbook of Chemical Bond Energies Sb–H bonds, 489 Sb–halogen bonds, 489 Se–H bonds, 451 Se–halogen bonds, 451 Si–Br bonds, 465 Si–Cl bonds, 464 Si–F bonds, 464 Si–H bonds, 455 Si–I bonds, 465 Sn– Br bonds, 475–476 Sn– Cl bonds, 475 Sn– F bonds, 475 Sn– H bonds, 473 Sn– I bonds, 476 Te–H bonds, 453 Te–halogen bonds, 453 Rare gas complexes anions, 1452 cations, 1446–1452 neutrals, diatomic, 1429–1436 polyatomic, 1436–1446 Rb-containing species neutrals, 557–559 RbC clusters, 559– 562 RbK clusters, 562– 563 Re-containing species neutrals,796–799 ReC clusters, 799–801 ReK clusters, 801 Rh-containing species neutrals, 882–892 RhC clusters, 892 –894 Ru-containing species neutrals, 840–848 RuC clusters, 849 –851

S S acids RC(O)SH, see Thio-acids Sb-containing compounds Sb–As bonds, 490 Sb–Bi bonds, 490 Sb–C bonds, 489 Sb–H bonds, 489 Sb–halogen bonds, 489 Sb–N bonds, 490 Sb–O bonds, 489 Sb–P bonds, 490 Sb–Pb bonds, 489 Sb–S bonds, 490 Sb–Sb bonds, 489 Sb–Te bonds, 490 Sc-containing species neutrals, 601–603 ScC clusters, 603– 606 Se-containing compounds Se–C bonds, 452 Se–H bonds, 451 Se–halogen bonds, 451 Se–N bonds, 452

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Index of Compound Classes Se–O bonds, 452 Se–P bonds, 452 Se–S bonds, 452 Se–Se bonds, 451 Se–Te bonds, 452 Selenium clusters/complexes anions, 1346 cations, 1341–1346 neutrals, 1341 Si-containing compounds C–H bonds, 100, 131, 133 C–O bonds, 344 N–C bonds, 418 N–H bonds, 377 O –H bonds, 261, 304 O –O bonds, 315 Si–Br bonds, 465 Si–C bonds, 460–462 Si–Cl bonds, 464–465 Si–F bonds, 463–464 Si–Ge bonds, 467 Si–H bonds, 455 –459 Si–I bonds, 465 Si–Mn bonds, 467 Si–N bonds, 463 Si–O bonds, 462– 463 Si–P bonds, 466 Si–S bonds, 466 Si–Se bonds, 450,466 Si–Si bonds, 459 –460 Si–Sn bonds, 467 Si–Te bonds, 466 Silicon neutral complexes anions, 1153 cations, 1147–1152 neutrals, 1140 –1147 Sm-containing species neutrals, 623 –626 SmC clusters, 626 Sn-containing compounds O –O bonds, 315 Sn–Br bonds, 475– 476 Sn–C bonds, 476–477 Sn–Cl bonds, 475 Sn–F bonds, 475 Sn–Ge bonds, 475 Sn–H bonds, 473 –474 Sn–I bonds, 476 Sn–O bonds, 477 Sn–Pb bonds, 475 Sn–S bonds, 477 Sn–Se bonds, 477 Sn–Si bonds, 467 Sn–Sn bonds, 474 –475 Sn–Te bonds, 477 Sr-containing species neutrals, 591 –593 SrC clusters, 593– 595 Sulfates O –S bonds, 362– 363 Sulfenate RSOR

1631 O –C bonds, 345 O –S bonds, 360–363 Sulfenic acid RSOH O –S bonds, 363–364 S– C bonds, 442 Sulfides RSR 0 , disulfides RSSR 0 C –C bonds, 203–204 C –H bonds aliphatic, 125–126 aromatic, 128 cyclic, 126 –128 O-containing, 127, 129 Si-containing, 131 N–H bonds, 375, 376 O –H bonds, 302 S– C bonds, 438 –439 S– H bonds, 430 S– O bonds, 364 Sulfonamides RSO2NR2 N–H bonds, 374 Sulfones RSO2R 0 C –H bonds aliphatic, 129 aromatic, 129, 131 di-sulfonyl, 130 C –S bonds, 442 N–H bonds, 374, 376 N–N bonds, 440 N–S bonds, 421 O –C bonds, 364 S– halogen bonds, 446 S– O bonds, 363–364 Sulfonic acids RSO3H O –H bonds, 261 O –S bonds, 363 Sulfoxides RSOR 0 C –H bonds, 129 S– C bonds, 442 S– H bonds, 428 S– halogen bonds, 446, 447, 448 S– O bonds, 364 Sulfur clusters/complexes, 917 anions, 1331– 1341 cations, 1325–1331 neutrals, 1323–1324

T Ta-containing species neutrals, 708–711 TaC clusters, 711–712 Tb-containing species neutrals, 630–631 TbC clusters, 631 Tc-containing species neutrals, 785 TcC clusters, 795 –796 Tellurides or Te-containing compounds Te–H bonds, 453 Te–halogen bonds, 453

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1632 Te–O bonds, 453 Te–P bonds, 454 Te–S bonds, 453 Te–Sb bonds, 456 Te–Se bonds, 453 Te–Te bonds, 454 Tellurium cations, 938 –942 anions, 1349 cations, 1346–1349 Th-containing species neutrals, 643–650 ThC clusters, 650–651 Thiazyl compounds NSR N–S bonds, 420–421 Thio-acid RC(O)SH S–C bonds, 438 S–H bonds, 438 Thio-aldehydes RC(S)H C– H bonds, 125 Thio-amides RC(S)NR2 0 N–H bonds, 372 Thio-esters RC(O)SR 0 S–C bonds, 440 Thio-ketones RC(S)R 0 C– Cl bonds, 231 N–H bonds thiourea, 372 Thiols RSH and ArSH C– C bonds aliphatic, 203–204 aromatic, 204 diiols, 204 C– H bonds, 128 N–S bonds, 420 S–C bonds aliphatic, 436–438 aromatic, 438 cyclic, 437, 438 S–H bonds aliphatic, 426–427 aromatic, 427–428 halogened, 425, 428 thio-a-tocopherols, 430 S–O bonds, 360, 363 Thiones N–H bonds, 372 S–As bonds, 450 S–P bonds, 449 S–Sb bonds, 450 Ti-containing species neutrals, 667–673 TiC clusters, 673–678 TiK clusters, 678

Comprehensive Handbook of Chemical Bond Energies Tin clusters/complexes anions, 1159 cations, 1157 –1159 neutrals, 1156–1157 Tl-containing species neutrals, 1084– 1085 TlC clusters, 1086 Tm-containing species neutrals, 637–638 TmC clusters, 638–639

U U-containing species neutrals, 651–660 UC clusters, 660–662

V V-containing species neutrals, 689–691 VC clusters, 692–699 VK clusters, 699–700

W Water O–H bonds, 255 W-containing O–C bonds, 345 W-containing species neutrals, 751–777 WC clusters, 778 –780 WK clusters, 780

Y Y-containing species neutrals, 607–609 YC clusters, 610–611 Yb-containing species neutrals, 639–640 YbC clusters, 640

Z Zn-containing species neutrals, 1027– 1030 ZnC clusters, 1031–1033 Zr-containing species neutrals, 679–683 ZrC clusters, 683 –685

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Index of compound names A aceanthrenone, 1-, 92 aceanthrenone, 2-, 92 acenaphthene, 57 acenaphthenone, 1-, 92 acenaphthylene radical, 57 acenaphthylene, 56 acetadehyde, 83, 85, 181 acetaldimine, 412 acetamide, 199, 373, 414 acetenyl radical, 135 acetic acid anhydride, 97 acetic acid ethyl ester, 96 acetic acid isopropyl ester, 97 acetic acid methyl ester, 96, 189 acetic acid phenyl ester, 97, 336 acetic acid, 93, 187, 262, 334 acetic anhydride, 337 acetic ion, 93 acetohydrazide, 374 acetone, 85 acetonitrile pyridinium chloride, 1-, 108 acetonitrile trimethyl-ammonium chloride, 1-, 108 acetonitrile, 106, 192 acetyl bromide, 241 acetyl chloride, 85, 181, 229 acetyl fluoride, 85, 181, 216 acetyl iodide, 252 acetyl peroxide, 341 acetyl peroxy, 341 acetylamino acetic acid, 2-, 120 acetylamino propanioc acid, 2-, 120 acetylene, 24, 154 acetylene, substituted, 24 acyl peroxides, 317, 319 adamantane, 39 adamantanol, 1-, 259, 323 adamantyl bromide, 1-, 239 adamantyl chloride, 1-, 226 adamantyl compounds, 154

adamantyl iodide, 1-, 252 adamantyl nitrate, 1-, 344 adduct of BH3 and S(CH3)2, 126 adduct of hydroxycyclohexadienyl, 341 adduct of OH and SCS, 263 adduct, 364 adenine, 392 alanine anhydride, 121 alanine, 189, 190, 199 alklyl-1,3-dithianes, 4-, 121 alkoxy acids, 265 alkyl ethyl disulfide, 442 alkyl ethyl polysulfide, 442 alkyl hydroperoxide, 268, 312 alkyl hydrotrisulfide, 433 alkyl nitrate, 350, 353 alkyl nitrite, 350 alkyl phenyl disulfide, 442 alkyl tetrasulphide radicals, 435 alkyl thiol, 427 alkyl trisulphide radicals, 435 alkyl-1,3-dithiepanes, 2-, 128 alkyl-1,3-dithiolanes, 2-, 126 alkyl-2H-3,4,5,6-tetra-hydropyrans, 2-, 79 alkyldioxaborolanes, 133 alkylhydrodifulfide, 432 alkyloxy(2-nitrophenyl)amine, 381 alkyl-thio-2H-3,4,5,6-tetra-hydropyrans, 2-, 127 allene, 26 allyl hydroperoxide, 268 allyl alcohol, 71, 178, 321 allyl methyl ketone, 86 allyl methyl sulphone, 381, 443 allyl peroxy, 239 allyl phenyl ether, 331 allyl radical, 136 allyl triphenyl phosphonium, 30 aminino-benzeneacetic acid, a-, 419 amino-acid, 429 amino-3-quinoixalinecarbo-nitrile-1,4-dioxide, 2-, 358 amino-3-sulfanylpropanoic acid, 2-, 429 amino-4-methyl-3-sulfanylpentanoic acid, 2-, 429

1633

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1634 aminoazobenzene, p-, 417 aminoethan-1-ol, 2-, 180 aminoethane-1-thione, 1-, 372 aminoethanenitrile, 2-, 108 aminomethanamidine, 372 aminomethylnitrosoamino, 299 amino-N-nitroso-N-phenyl-amide, substituted, 399 aminophenylmethane-1-thione, 372 aminopyridine, 389 aminotriphenylphosphonium bromides, 383 ammonia, 369 amonomethanenitrile, 372, 419 aniline phosphonium bromide, substituted, 383 aniline, 378, 413 anilines, di- and trisubstituted, 379 anilines, substituted, 378 anisole, 8, 329 anisoles, substituted, 329 anthracenes, substituted, 58 anthracenyl hydroperoxide, 9-, 271 anthracenyl bromide, 9-, 241 anthracenyl-2 phenyl ketone, 88 anthracenyl-9 phenyl ketone, 88 anthracenylmethanes, substituted, 9-, 57 antimony arsenide, 488, 490 antimony bromide, 489 antimony chloride, 489 antimony clusters, 489 antimony fluoride, 489 antimony hydrides, 489 antimony monosulfide, 490 antimony monotelluride, 490 antimony monoxide, 489 antimony nitride, 490 antimony phosphide, 487, 490 antion, 306 arsenic chloride, 488 arsenic clusters, 487 arsenic fluoride, 487 arsenic hydrides, 487 arsenic iodide, 488 arsenic monoselenide, 488 arsenic monosulfide, 488 arsenic monoxide, 488 arsenic nitride, 488 arsenic phosphide, 488 artemisinin, 320 ascaeidole, 239 aza-1,2-diphenyl-vinyl phenylamine, (1Z)-, 375 aza-1-diazo-2,2,2-trinitroethane, 1-, 405 aza-1-diazo-2,2,2-triphenylethane, 1-, 405 aza-1-diazo-2,2-dinitroprop-1-ene, 1-, 304 aza-1-diazo-2-phenylethane, 1-, 405 aza-1-diazoethane, 1-, 404 aza-1-diazopent-1-en-3-one, 1-, 403 aza-1-methyoxy-3-phenyl-2-benzylpro-1-ene, 1-, 111 aza-2-methoxy-1,1-phenylvinylamine, 1Z-2-, 118 aza-3-diazoprop-3-en-1-ol, 3-, 405 aza-4-diazobut-4-en-2-one, 4-, 402 aza-bicyclo(2.2.1)heptan-7-ol, 7-, 282 azacyclohexyldiazomethen, 404

Comprehensive Handbook of Chemical Bond Energies azacyclopentyldiazomethen, 405 azadiazophenylmethane, 404 azaprop-1-ene, 2-, 102 azide cation, 396 azide radical, 396 azo-2-butane, 416 azobenzene, 417 azobenzene-N,N-dioxides, substituted, 403 azobutane, 416 azoethane, 416 azohexafluoroethane, 416 azoisobutane, 416 azoisopropane, 416 azomethane, 416 azo-N,N-dioxides, 403 azotertbutane, 416 azotoluene, 417 azoxy compounds, 356 azoxybenzenes, substituted, 356

B benzaldehyde, 84, 183 benzaldehyde, substituted, 84 benzamide, 200, 373, 411 benzanthrene, 59 benzenacetic acid, 94 benzenamine, 413 benzendisulfur radicals, 444 benzene, 40 benzene, substituted, 40-41, 301 benzenecarbohydrazide, 374 benzenecarboxamidine, 375 benzenemethanethiol, 438 benzeneperoxycarboxylic acid, 269 benzenesulfonamide, 374 benzenethiol, 427, 428, 438 benzenethiol, substituted, 427 benzo furoxans, 359 benzoanisole, 3,4-, 331 benzo-cyclo-butadiene, 47 benzo-cyclo-butene, 47 benzo-cyclo-butenone, 47 benzo-cyclo-propene, 47 benzofluorence, 1,2-, 59 benzofluorence, 2,3-, 60 benzofurazan N-oxides, substituted, 355 benzoic acid, 145, 192, 193, 251 benzoic acids, substituted, 264 benzoic anhydride, 337 benzolphenoxy methyl-naphthalene, 1-, 331 benzonitrile N-oxide, substituted, 355 benzonitrile, 193 benzonyl chloride, 183 benzoyl bromide, 242 benzoyl chloride, 229 benzoyl iodide, 252 benzoylthiolate, substituted, 429 benzyl alcohol, 72, 179, 259, 323 benzyl azide, 402 benzyl azide, p-NO2-, 403

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Index of Compound Names benzyl bromide, 241 benzyl chloride, 227 benzyl chloride, substituted, 227 benzyl dibutylsulfonium, substituted, 131 benzyl dimethylamine, 198, 415 benzyl dimethylsulfonium bromide, 131 benzyl hydroperoxide, 269 benzyl hydroperoxide, p-NO2-, 269 benzyl iodide, 251 benzyl methyl ether, substituted, 75 benzyl methyl ketone, 87, 185 benzyl methyl sulphide, 440 benzyl methyl sulphone, 129, 443 benzyl methylamine, 198, 414 benzyl nitrosothio, 420 benzyl peroxy, 340 benzyl phenyl ketone, 88, 185, 186 benzyl phenyl sulfide, 440 benzyl phenyl sulphide, 128 benzyl phenyl sulphone, 130 benzyl pyridine, 2-, 115 benzyl pyridine, 3-, 116 benzyl pyridine, 4-, 116 benzyl pyridinium chloride, 1-, 117 benzyl radical, 139 benzyl tert-butyl sulphone, 130 benzyl trifluoromethyl sulphone, 130 benzyl trimethylammonium bromide, 105 benzyl trimethylammonium chloride, 105 benzyl-1,3-oxazolidin-2-one, 4-, 387 benzylamine, 371, 413 benzylcyanide, 194, 195 benzylidene N-oxides, substituted, 356 benzylphenylthioamine, 273 biacetyl, 186 bibenzoyl, 186 bibenzyl ketone, 186 bibenzyl, 164 bicyclo-octane, 37 bifluoroformyloxy, 316 bipentafluorophenyl, 177 biphenols, 292 biphenyl, 164 bis(1,1-dimethyl-1-silaethyl)-amine, 377 bis(1,1-dimethyl-silaethyl)-methylamine, 418 bis(4-hydroxyphenyl)methane, 45 bis(difluoroamino) propane, 2,2-, 411 bis(difluoromethyl) ether, 74 bis(dimethylphosphino)methane, 133 bis(fluorosulfuryl)fluoramine, 421 bis(phenylamino)methne-1-thione, 372 bis(trifluoroacetyl) peroxide, 317, 338 bis(trifluoromethyl) peroxide, 338 bis(trifluoromethyl) peroxy-dicarbonate, 317 bis(trimethylsilyl)methane, 133 bismuth antimonide, 490, 492 bismuth bromide, 491 bismuth chlorides, 491 bismuth clusters, 391 bismuth fluorides, 491 bismuth hydrides, 490

1635 bismuth iodide, 491 bismuth monoselenide, 491 bismuth monosulfide, 491 bismuth monoxide, 491 bismuth phosphide, 487, 492 bismuth telluride, 492 bromine dioxide, 367 bromine hydroperoxide, 310 bromo peroxy, 367 bromo trioxide, 367 bromo-1,1-difluoroethane, 1-, 170, 236 bromo-1-chloro-2,2,2-trifluoroethane, 1-, 66, 168, 236 bromo-1-phenylethan-1-one, 2-, 242 bromo-1-propene, (E)-1-, 237 bromo-1-propene, (Z)-1-, 237 bromo-1-propene, 3-, 237 bromo-2,2,2-trifluoroethane, 1-, 168 bromo-2,2-dimethyl-propane, 1-, 239 bromo-2,6-piperidione, 1-, 424 bromo-2-chloro-1,1,2-trifluoroethane, 1-, 170 bromo-2-chloroethane, 1-, 172, 237 bromo-2-methyl-butane, 2-, 239 bromo-2-methyl-propane, 1-, 238 bromo-2-methylpropane, 2-, 238 bromoacetic acid, 187 bromoacetic acid, 2-, 242 bromoacetone, 1-, 242 bromoacetone, 183 bromo-alkanes, 1-, 238 bromo-alkanes, 2-, 238 bromobenzenes, substituted, 240 bromo-but-1-nen, 3-, 238 bromo-but-1-nen, 4-, 238 bromobutane, 1-, 138, 174 bromobutane, 2-, 138, 174 bromochlorodifluoromethane, 212, 234 bromochloroethane, 1,1-, 171, 223, 237 bromochlorofluoroiodomethane, 234, 245 bromochlorofluoromethane, 63, 212, 213 bromochloroiodomethane, 245 bromochloromethane, 63, 219, 220, 234 bromochloromethyl radical, 140 bromo-cyclo-heptane, 239 bromo-cyclo-hexane, 239 bromodichlorofluoromethane, 219, 234 bromodichloroiodomethane, 245 bromodichloromethane, 63, 234 bromodiiodomethane, 235 bromodispiro[2.1.2.0]heptane, 1-, 239 bromodispiro[2.1.2.1]octane, 1-, 240 bromo-eth-1-yl radical, 1-, 142 bromo-eth-1-yl radical, 2-, 142 bromoethane, 67, 172, 237 bromoethanenitrile, 2-, 236 bromoethyl benzene, 2-, 241 bromoethylbenzene, 1-, 241 bromoethyne, 167, 235 bromofluoromethane, 213, 234 bromo-heptafluoropropane, 1-, 237 bromo-heptafluoropropane, 2-, 238 bromohexane, 1-, 175

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1636 bromoiodomethane, 235, 245 bromo-isopropyl benzene, 1-, 241 bromomethane, 64, 235 bromomethyl hydroperoxide, 267 bromomethyl benzene, 176 bromonaphthalene, 1-, 241 bromonaphthalene, 2-, 241 bromonitrooxy, 349, 350, 367 bromopentafluorobenzene, 240 bromopentafluoroethane, 236 bromopentane, 1-, 175 bromoperoxide, 311 bromopropane, 1-, 237 bromopropane, 2-, 237 bromopropanoic acid, 2-, 242 bromopropanoic acid, 3-, 242 bromopropene, 1-, 69 bromosilane, 465 bromosilane-1,1,1-triol, 465 bromotoluenes, substituted, 240 bromotrichloromethane, 219, 234 bromotrifluoromethane, 233 bromotriiodomethane, 235 bromotrinitromethane, 243 bromovinyl benzene, 1-, 240 bromovinyl benzene, 2-, 241 but-1-en-3-yne, 155 buta-1,2-diene, 26 buta-1,3-diyne, 155 butadien-4-yl radical, 1,2-, 137 butadiene, 1,2-, 156 butadiene, 1,3-, 156 butadiene, 2-methyl, 1,3-, 156 butan-3-yl radical, 1-, 137 butanal, 182, 183 butane, 20, 147, 148 butane-1,3-diol, 73 butane-2,3-diol, 73 butane-2,3-dione, 90 butanedinitrile, 195 butanedioic acid, 95, 190 butanediol, 1,4-, 73 butanediol, 2,3-, 180 butanenitrile, 193, 194 butanethiol, 1-, 203, 437 butanethiol, 2-, 437 butanoic acid, 187, 190, 262, 334, 335 butanol, 1-, 179, 257, 322 butanol, 2-, 179, 257, 322 butanoyloxy butanoate, 317 buten-1-ol, 3-, 179 buten-3-yl radical, 1-, 136 buten-4-yl radical, 1-, 136 butenal, (Z)-2-, 182 butene, (E)-2-, 26, 156 butene, (Z)-2-, 26, 156 butene, 1-, 27, 156 butenenitrile, 2-, 192, 193 butenenitrile, 3-, 193, 194 butenyl-2-peroxy, 340 butoxyethyl benzene, 1-, 331

Comprehensive Handbook of Chemical Bond Energies butyl acetate, 335 butyl alcohol, 71, 258 butyl methyl ether, 327 butyl methyl ketone, 185 butyl methyl sulphide, 438 butyl methyl sulphone, 443 butyl nitrine, 343 butyl nitrite, 349 butyl tert-butyl ether, 328 butyl vinyl ether, 327 butylamine, 1-, 412 butylamine, 102 butylamine, 2-, 412 butylbenzene, 162 butyl-cyclo-hexane, 154 butyn-1-ol, 3-, 179 butyne, 1-, 24, 135 butyne, 2-, 24, 135 butynedinitrile, 2-, 192, 196 bytadiene, 1,3-, 26

C caprolactone, 3-, 100 carbazole, 392 carbazole, 9H-, 386 carbene, 136 carbon dioxide, 342 carbon disulfide, 436 carbon monosulfide, 436 carbon monoxide, 342 carbon oxysulfide, 342, 436 carbon phosphide, 484 carbonyl chloride, 229 carboxylic acid, 93 carboxylic acid, substituted, 95 cationic niobium h2-acyl, 44 CH2N radicals, 404 chloramide, 423 chlorine azide, 423 chlorine dioxide, 366 chloro peroxy, 366 chloro trioxide, 367 chloro-1,1,2-trifluoro-2-iodo-ethane, 1-, 247 chloro-1,2,2-trifluoro-ethane, 2-, 66 chloro-1-fluoroethane, 1-, 170 chloro-1-phenylethan-1-one, 2-, 229 chloro-1-propene, 3-, 223 chloro-2,2,2-trifluoro-ethane, 1-, 66 chloro-2,2-dimethyl-propane, 1-, 225 chloro-2-bromoethane, 1-, 247 chloro-2-butene, 1-, 224 chloro-2-fluoro-ethylene, (Z)-1,2-, 68 chloro-2-iodo-ethane, 1-, 247 chloro-2-methyl-1-propene, 3-, 213 chloro-2-methylbutane, 2-, 225 chloro-2-methylethyl-peroxy, 2-, 340 chloro-2-methylpropane, 1-, 224 chloro-2-methylpropane, 2-, 224

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Index of Compound Names chloro-2-nitrosopropane, 2-, 406 chloro-3-methyl-butane, 2-, 175 chloroacetamides, 230, 231 chloroacetic acid methyl ester, 189 chloroacetic acid, 2-, 229, 262 chloroacetic acid, 93, 187 chloroacetone, 184 chloroacetyl chloride, 182 chloroacetyl chloride, 2-, 229 chloroalkanes, 1-, 225 chloroalkanes, 2-, 225 chloroallyl peroxy, 2-, 340 chlorobenzenes, substituted, 226 chloro-but-1-ene, 3-, 225 chloro-but-1-ene, 4-, 225 chlorobutane, 1-, 174, 175, 224 chlorobutane, 2-, 174, 224 chlorobutene, 4-, 174, 224 chloro-cyclo-hentane, 226 chloro-cyclo-hexane, 226 chlorocyclohexane, 227 chlorodifluoromethane, 62, 218 chlorodifluoromethyl nitroperoxy, 351 chlorodifluoromethyl peroxy, 338 chlorodifulfide, 447 chlorodiiodomethane, 220 chlorodisulfane, 432 chloro-eth-1-yl radical, 1-, 142 chloro-eth-1-yl radical, 2-, 142 chloroethane, 67, 171, 223 chloroethanenitrile, 2-, 210 chloroethlene, 167 chloroethyl benzene, 2-, 228 chloroethyl ethyl ether, 1-, 326 chloroethyl ethyl ether, 2-, 326 chloroethyl hydroperoxide, 2-, 267 chloroethyl methyl ether, 1-, 326 chloroethyl methyl ether, 2-, 325 chloroethyl peroxy, 2-, 339 chloroethyl vinyl ether, 2-, 325 chloroethylbenzene, 1-, 228 chloroethylene, 68 chloroethylsulfone, 448 chloroethyne, 167, 220 chlorofluoromethane, 62, 211, 212, 218 chlorofluoromethyl radical, 140 chlorofluorotrioxide, 316 chloroformyl chloride, 361 chloroformyl fluoride, 216, 229 chlorohexane, 2-, 175 chloroiodomethane, 220, 245 chloro-isopropyl benzene, 1-, 228 chloromethane, 63, 210 chloromethyl benzene, 176 chloromethyl hydroperoxide, 267 chloromethyl hydro-peroxide, a-Co2 K-, 270 chloromethyl peroxy, 339 chloromethyl pyridines, 231 chloromethyl radical, 140 chloromethylene, 140 chloromethylsulfone, 448

1637 chloromethylthio, 447 chloromethylthiomethane, 231 chloronaphthalene, 1-, 228 chloronaphthalene, 2-, 228 chloronitrooxy, 348, 350, 367 chlorooxirane, 2-, 191 chloropentafluorobenzene, 227 chloropentafluoroethane, 168, 221 chloropentane, 1-, 175, 225 chloroperoxide, 311 chlorophenylsulfone, 448 chlorophenylthio, 447 chloro-pro-1-yl radical, 1-, 142 chloro-pro-2-yl radical, 2-, 142 chloropropane, 1-, 68, 173, 223 chloropropane, 2-, 173, 223 chloropropanoinc acid, 2-, 187 chloropropene, 1-, 68, 223 chloropropionic acid, 2-, 230 chloropropylsulfone, 448 chloropyrazine, 232 chloro-ropropanoic acid methyl ester, 1-, 190 chlorosilane, 464 chlorosilane-1,1,1-triol, 465 chlorothioformyl chloride, 231 chlorotrifluoroethele, 166 chlorotrifluoroethylene, 214, 220 chlorotrifluoromethane, 218 chlorotriiodomethane, 220 chlorotrioxide, 316 chloro-vin-1-yl radical, 1-, 141 chroman-6-ol, substituted, 293 chromane, 294, 344 chromene, substituted 2,2,5,7,8-pentamethyl, 2H-, 295 chromium tricarbonyl, 89 cinnamyl-4-nitrobenzenr sulfenate, 345 cis-cis-peronitrous acid, 311 cis-hydroxystilbene substituted, 304 CN radical, 403 CNN radicals, 404 coenzyme B12, substituted, 203 CoII(H2bim), 395 cubane, 37 cyanoacetic acid, 2-, 120 cyanoamino radical, 370 cyanogen azide, 404 cyanogen bromide, 233 cyanogen chloride, 218 cyanogen fluoride, 211 cyanogen iodide, 243 cyanogen, 191 cyclic hydroperoxides, 271 cyclo-1-ene-1,2-dicarrboxylic acid, 94 cyclo-butacarboxylic acid, 94 cyclo-butalcarboxylic acid, 94 cyclo-butane, 32 cyclo-butanecarbonitrile, 193 cyclo-butanecarboxylic acid, 263 cyclo-butyl radical, 137 cyclo-butylacetic acid, 2-, 263

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1638 cyclo-butylamine, 412 cyclo-decane, 39 cyclo-dodecane, 39 cyclo-heptadiene, 1,3-, 36 cyclo-heptane, substituted, 36 cyclo-heptanecarboxylic acid, 264 cyclo-heptatriene, 1,3,5-, 36 cyclo-heptene, 30 cyclo-heptenyl radical, 138 cyclo-heptyl radical, 139 cyclo-hetyl peroxy, 340 cyclo-hex-1-enecarboxylic acid, 94 cyclo-hexa-1,3-dien-5-yl radical, 138 cyclo-hexa-1-en-3-yl radical, 138 cyclo-hexacarboxylic acid, 94 cyclo-hexadiene, 1,3-, 34 cyclo-hexadiene, substituted, 1,4-, 34 cyclo-hexadienyl peroxy, 340 cyclo-hexadione, 1,3-, 259 cyclohexalacetic acid, 2-, 264 cyclo-hexalamines, substituted, 113 cyclo-hexane, substituted, 35–36 cyclo-hexanecarbonitrile, 193 cyclo-hexanecarboxylic acid, 264 cyclo-hexanethiol, 427, 438 cyclo-hexanol, 72, 323 cyclo-hexanone, 91 cyclo-hexanone, oximes, 273 cyclo-hexaxyl-cyclo-hexane, 154 cyclo-hexene, 35 cyclo-hexene, substituted, 35 cyclo-hexenyl peroxy, 340 cyclo-hexyl azide, 402 cyclo-hexyl hydroperoxide, 338 cyclo-hexyl methyl ether, 75 cyclo-hexyl nitrosothio, 420 cyclo-hexyl radical, 138 cyclo-hexyl-2-phenyl-ethanenitrile, 2-, 107 cyclo-hexylamine, 413 cyclo-hexylbenzene, 45 cyclo-nonanes, substituted, 38 cyclo-octadiene, 38 cyclo-octane, substituted, 38 cyclo-octanyl radical, 139 cyclo-octene, 39 cyclo-penen-1-ol, 259 cyclo-pent-2-en-1-ol, 72 cyclo-pentadiene, substituted, 1,3-, 32 cyclo-pentane, substituted, 39 cyclo-pentanecarbonitrile, 193 cyclo-pentanecarboxylic acid, 263 cyclo-pentanethiol, 437 cyclo-pentanol, 323 cyclo-pentanone, substituted, 91 cyclo-pent-en-3-yl radical, 137 cyclo-pentene, 33 cyclo-pentene, 3-methyl, 160 cyclo-pentyamine, 413 cyclo-pentyl methyl sulphide, 439 cyclo-pentyl radical, 137 cyclo-pentylacetic acid, 2-, 264

Comprehensive Handbook of Chemical Bond Energies cyclo-pentylbenzene, 45 cyclo-pentylpropene, 3-, 161 cyclo-pexanol, 259 cyclo-propane, 31 cyclo-propanecarboxylic acid, 263 cyclo-propene, 31 cyclo-propyl methyl radical, 137 cyclo-propyl radical, 137 cyclo-propylamine, 412 cyclo-propylbenzene, 162 cyclo-undecane, 39 cyclo-undercanane, oximes, 273

D deca-2,7-diene, E,E-, 30 decalin, (E)-, 39 decalin, (Z)-, 39 decanal, 83 decanethiol, 427 decanoic acid, 263, 334 decanol, 72 decediene, Z,Z-2,8, 30 decyne, 5-, 25 dehydro-1,3-quinodimethane, 5-, 40 deuterated ammonias, 369 di(2-naphthyl)amine, 386 di(ethyl sulphonyl) methane, 130 di(isopropyl sulphonyl) methane, 130 di(methyl sulphonyl) methane, 130 di(pentafluorophenyl)-acetonitrile, 107 di(phenyl sulphonyl) methane, 130 di(phenylthio) methane, 131 di(phenylthio)phenyl methane, 128 di(sulfur pentafluoro) peroxide, 315 di(sulfur pentafluoro) trioxide, 315 di(t-butyl sulphonyl) methane, 130 di(trifluoromethyl sulphonyl) methane, 130 di(a-CN-propyl)phosphine, 482 di-2-naphthamine, 377 diacelhydrazine, 374 diacetamide, 374 diacetyl peroxide, 317 diacetylene, 24 dialkel-1,3-dithianes, 2,4-, 127 dialkyl disulfide ions, 435 dialkyl disulphide, 433 dialkyl peroxide, 314 dialkyl polysulfide, 434 dialkyl tetrasulfide, 434 di-alkyloxyethanes, 1,1-, 76 di-alkyloxy-isobutanes, 1,1-, 76 dialkyloxymethenes, 76 di-alkyloxy-toluene, 1,1-, 77 diaryl-4-phenyl-1,2,3,4-tetrahydro-sym-tetrazines, 2,6-, 394 diazabicyclo(2.2.2)octane, 1,4-, 113 diazabicyclo[2.2.1]-hept-2-ene N-oxide, 2,3-, 355 diazabicyclo[2.2.1]-hept-2-ene N-oxide, 2,3-, 357 diazaperhydroine-2,5-diones, substituted, 1,4-, 124

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Index of Compound Names diazene, 369 diaziridine, 1,2-, 387 diazocarbene, 112 diazomethyl radical, 111 diazomethylene, 404 dibenzo(b,f)azepine, 5H-, 393 dibenzo(b,f)azepine, 5H,10H,11H-, 393 dibenzoylhydrazine, 374 dibenzyl ether, substituted, 75 dibenzyl ketone, 88 dibenzyl sulphide, 204 dibromine oxide, 367 dibromo-1,1,2,2-tetrafluoroethane, 1,2-, 236 dibromo-1,2-dichloro-ethane, 1,2-, 171 dibromo-1-chloro-2,2,2-trifluoroethane, 1,1-, 236 dibromo-2-phenylethyl benzene, 1,2-, 241 dibromo-9-nitrosocarbazole, 3,6-, 401 dibromobutane, 1,4-, 174 dibromobutane, 2,2-, 175 dibromobutane, 2,3-, 174 dibromocarbazole, 3,6-, 393 dibromochlorofluoromethane, 162, 213, 234 dibromochloroiodomethane, 245 dibromochloromethane, 63, 219, 234 dibromodichloromethane, 219, 235 dibromodifulfide, 446 dibromoethane, 1,1-, 67, 171 dibromoethane, 1,2-, 171, 172 dibromoethylene, (E)-1,2-, 230 dibromoethylene, (Z)-1,2-, 235 dibromofluoromethane, 213 dibromoiodomethane, 245 dibromomethane, 64, 235 dibromomethyl radical, 140 dibromopropane, 1,2-, 173 dibromopropane, 1,3-, 237 dibutyl disulphide, 433 dibutyl ether, 74, 328 dibutyl ketone, 87 dibutyl peroxide, 213 dibutylamine, 103 dibutylphosphine, 482 dibutylthio-3-methylbutane, 1,1-, 126 dichlorine dioxide, 366 dichlorine monoxide, 366 dichlorine trioxide, 311, 366 dichloro-1,1,1-trifluoropropane, 3,3-, 173 dichloro-1-nitro-propane, 1,1-, 407 dichloro-2-butene, 1,4-, 224 dichloro-2-hydro-peroxyethane, 2,2-, 269 dichloro-2-hydroperoxy-ethanenitrile, 2,2-, 270 dichloroacetic acid, 2,2-, 229 dichloroacetyl chloride, 182 dichlorobutane, 1,2-, 175 dichlorobutane, 1,3-, 173 dichlorobutane, 1,4-, 174 dichlorodifluoromethane, 212, 218 dichlorodifulfide, 447 dichlorodisulfane, 432 dichloro-eth-1-yl radical, 1,1-, 142 dichloro-eth-1-yl radical, 1,2-, 142

1639 dichloro-eth-1-yl radical, 2,2-, 142 dichloroethane, 1,1-, 66, 171 dichloroethane, 1,2-, 171 dichloroethanenitrile, 2,2-, 229 dichloroethlene, 1,1-, 167, 222 dichloroethlene, 1,2-, 167, 222 dichloroethyl hydroperoxide, 2,2-, 267 dichloroethyl peroxy, 2,2-, 339 dichloroethylene, (E)-1,2-, 67, 221 dichloroethylene, (Z)-1,2-, 221 dichloroethylene, 1,2-, 221 dichloroethyne, 1,2-, 167, 220 dichloroethyne, 221 dichlorofluoromethane, 62, 212, 218 dichlorofluoromethyl nitroperoxy, 351 dichlorofluoromethyl peroxy, 339 dichloroiodomethane, 245 dichloromethane, 63, 219 dichloromethyl benzene, 227 dichloromethyl hydroperoxide, 267 dichloromethyl hydro-peroxide, a-Co2 K-, 270 dichloromethyl peroxy, 339 dichloromethyl radical, 140 dichloroperoxide, 310 dichlorophenoxy-1 0 ,5 0 -dichloro-phenyl-6,2 0 -ether, 2,4-, 297 dichloropropane, 1,2-, 173 dichloropropane, 1,3-, 173, 223 dichlororopane, 2,2-, 173 dichlorotetrafluoroethane, 1,2-, 169 dichlorotetrafluoroethane, 221 dichloro-vin-1-yl radical, 1,2-, 141 dicyclo-hexylamine, 113 dicyclohexyloxymethane, 81 dicyclo-hexylphosphine, 482 didehydrophenyl radical, 3,5-, 139 didehydrophenyl, 3,5-, 40 diethoxy 2-phenylpropane-1,3-dione, 99 diethoxy sulfate, 363 diethyl 2-(1,1-dimethyl-1silaethyl) propane-1, 3-dioate, 100 diethyl 2,2-dibromopropane-1,3-dioate, 243 diethyl 2,2-dichloropropane-1,3-dioate, 230 diethyl 2-bromopropane-1,3-dioate, 243 diethyl 2-ethyl propane-1,3-dioate, 99 diethyl disulfide, 126, 433 diethyl ethane-1,2-dioate, 98 diethyl ether, 74, 325 diethyl ketone, 86, 184 diethyl peroxide, 313, 338 diethyl sulfoxide, 361 diethyl sulphide, 439 diethyl(iminophenylmethyl)-amine, 375 diethyl(nitrosophenylamino)-phosphino-1-one, substituted, 400 diethyl(phenylamino)-phosphino-1-one, 382 diethyl-1,3-dioxanes, 3,3-, 81 diethyl-2-germabutyl tert-butyl peroxide, 2,2-, 315 diethyl-2-stannabutyl tert-butyl peroxide, 2,2-, 315 diethylamine, 102 diethyl-ethanol, 1,1-, 258

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1640 diethylphosphine, 482 diethylphosphino diethyl-phosphine, 483 diethylsulfone, 362 diethylthio-3-methylbutane, 1,1-, 126 diethylthio-ethane, 1,1-, 126 difluorine monoxide, 365 difluoro disulfur, 432 difluoro(trifluoromethyl)-amine, 411 difluoro-1,1-diphenyl-propyl benzene, 3,3-, 178 difluoro-1-chloro-ethane, 1,1-, 66, 222 difluoro-1-iodoethane, 1,1-, 247 difluoro-2-chloroethylene, 1,1-, 67 difluoro-2-silaeth-1-ene, 461 difluoroamine, 422 difluoroamonia, 369 difluorobromoiodomethane, 244 difluorobromomethane, 62 difluorochloroiodomethane, 244 difluorodibromomethane, 234 difluorodiiodomethane, 244 difluorodisulfane, 432 difluoro-eth-1-yl radical, 1,1-, 141 difluoro-eth-1-yl radical, 2,2-, 141 difluoroethane, 1,1-, 65, 169 difluoroethane, 1,2-, 65, 169 difluoroethylene, (E)-1,2-, 67 difluoroethylene, 1,1-, 67, 167 difluoroethyne, 166, 214 difluoroiodomethane, 244 difluoromethane, 62, 211 difluoromethyl radical, 140 difluoromethyl trifluoromethyl ether, 74 difluorononane, 2,2-, 176 difluoroperoxide, 310 difluoropropyl benzene, 3,3-, 177 difluoro-vin-1-yl radical, 1,2-, 140 digermane, 470 dihydrioimidazole, substituted, 2,5-, 279– 280 dihydro-1,4-benzodioxin, 2,3-, 345 dihydro-1,4-dioxin, 2,3-, 344 dihydroacridine, substituted, 9,10-, 53 dihydroanthracene, substituted, 9,10-, 51 dihydrobenzo(b)furan-5-ol and its 1-thio, 1-seleno, and 1-telluro analogues, 2,3-, 296 dihydrobenzofuran, substituted, 295 dihydronaphthalene, 1,2-, 49 dihydronaphthalene, 1,4-, 49 dihydrophenanthrene, 9,10-, 59 dihydrophenanthridine, methanol, substituted, 5,6-, 284 dihydrophthalazine-1,4-dione, 2,3-, 392 dihydropyran, 2H-3,4-, 344 dihydropyrene, 1,2-, 60 dihydropyridines, substituted, 1,4-, 115, 391 dihydropyrrole, substituted, 2,5-, 277 dihydroquinoline, substituted, 1,2-, 284 dihydroxybutanedioic acid, 2,3-, 95 diiodo oxide, 368 diiodo-1,1,2,2-tetrafluoro ethane, 1,2-, 246 diiodoethane, 1,2-, 172 diiodofluoromethane, 213

Comprehensive Handbook of Chemical Bond Energies diiodomethane, 64, 246 diiodomethyl radical, 141 diiodoperoxide, 311 diiodopropane, 1,3-, 249 di-iso-propyl ketone, 87, 328 di-iso-propyl ether, 74 di-iso-propyl ketone, 87 di-iso-propyl peroxide, 313 di-iso-propylamine, 103 diketene, 191 dimethoxy sulfate, 362 dimethoxygermane, 469 dimethoxymethane, 336 dimethoxyphenylmethane, substituted, 77 dimethy-1-butene, 2,3-, 29, 159 dimethy-1-butyne, 2,2-, 155 dimethy-1-pentyne, 2,2-, 155 dimethybenzyl alcohol, 1,1-, 323 dimethyl- 1,4-dioxane, 2,5-, 81 dimethyl 2-methyl propane-1,3-dioate, 98 dimethyl benzylamine, 416 dimethyl bytane-1,4-dioate, 98 dimethyl disulfur, 432 dimethyl disulphide, 433, 441 dimethyl ether, 73, 325 dimethyl heptane-1,7-dioate, 98 dimethyl ketone, 183 dimethyl nonane-1,9-dioate, 98 dimethyl oxalate, 190 dimethyl pentane-1,5-dioate, 98 dimethyl peroxide, 312, 338 dimethyl phenyl silamethane, 458 dimethyl phenylamine, 416 dimethyl propanenitrile, 2,2-, 195 dimethyl pyrrolidin-3-one, 4,4-, 121 dimethyl sulfoxide, 129, 361, 442 dimethyl sulphide, 126, 438 dimethyl sulphone, 129, 442 dimethyl(methylamino)amine, 397 dimethyl-1-(phenylsulfonyl)-2-sila-vinylpropane, 2,2-, 131 dimethyl-1,3-butadiene, 2,3-, 28 dimethyl-1,3-dioxane-4,6-dione, 2,2-, 100 dimethyl-1,3-dioxanes, 3,3-, 100 dimethyl-1-butene, 2,3-, 158 dimethyl-1-butene, 3,3-, 158 dimethyl-1-nitrosopropane, 2,2-, 407 dimethyl-1-pentene, 2,4-, 160 dimethyl-1-pentene, 4,4-, 160 dimethyl-1-propanethiol, 2,2-, 204, 437 dimethyl-1-silaethyl dimethylamine, 1,1-, 463 dimethyl-1-silaethyl methylamine, 1,1-, 463 dimethyl-1-silaethyl-2,2,4,4,-tetramethyl-2,3, 4-trisilapentane, 3(1,1-, 356 dimethyl-1-silaethyl-2,2-dimethyl-1-(phenylsulfonyl)2-silapropane, 1-(1,1-, 131 dimethyl-1-silaethyl-3-germa-2,2,4, 4-tetramethyl-2,4-disilapentane, 3-(1,1-, 468 dimethyl-2,3-dinitrobutane, 2,3-, 201 dimethyl-2-butene, 2,3-, 27 dimethyl-2-chloro-propanol, 1,1-, 257

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Index of Compound Names dimethyl-2H-3,5,6-trihydropyran-4-one, 91 dimethyl-2-pentene, (E)-4,4-,160 dimethyl-2-pentene, (Z)-4,4-, 160 dimethyl-2-phenyl-propanol, 1,1-, 259 dimethyl-2-silapropane, 2,2-, 133 dimethyl-2-stannabutane, 2,2-, 476 dimethyl-3-hexene, (Z)-2,5-, 27 dimethylallyl alcohol, 2,3-, 72 dimethylamine, 102, 371, 414 dimethylamino acetate, 120 dimethylamino diazenyl dimethyl-anine, 397 dimethylamino-1-phenyl-ethan-1-one, 2-, 119 dimethylamino-2-propanone, 1-, 199, 418 dimethylaminomethanol, 324 dimethylamino-N-benzamide, 383 dimethylbenzyl alcohol, a,a-, 259, 323 dimethylbenzylamine, 104 dimethylbenzylamine, a?a-, 413 dimethyl-benzylcyanide, a?a-, 194, 195 dimethylbutane, 2,2-, 22, 148, 149 dimethylbutane, 2,3-, 22, 150 dimethylbutanedioic acid, 2,3-, 191 dimethyl-butanol, 1,1-, 258 dimethyl-cyclo-propene, 3,3-, 31 dimethylene-cyclo-butane, 1,3-, 31 dimethylethyl heptane 1,7-dioate, 99 dimethylethyl butane 1,4-dioate, 99 dimethylethyl decane 1,10-dioate, 89 dimethylethyl ethane-1,2-dioate, 99 dimethylethyl pentane 1,5-dioate, 99 dimethylethyl-N-(4-(1,1-dimethylethyl)phenyl)1-naphthalenamine, 4-(1,1-, 386 dimethylfulvene, 6,6-, 32 dimethylheptane, 2,2-, 152 dimethylhexane, 2,2-, 151 dimethyl-hexane, 2,3-, 151 dimethylhexane, 2,3-, 23 dimethylhexane, 2,4-, 152 dimethylhexane, 2,5-, 23, 151 dimethylhexane, 3,4-, 152 dimethylhydrazine, 1,1-, 112, 372, 397, 415 dimethylhydrazine, 1,2-, 397 dimethylnitroamine, 418 dimethylpentane, 2,2-, 150 dimethylpentane, 2,3-, 150 dimethylpentane, 2,4-, 42, 126 dimethyl-pentane, 3,3-, 149 dimethylpenylamine, 104 dimethylphenylphosphino-1-thione, 450, 486 dimethylpropan-1-ol, 2,2-, 71 dimethylpropane, 2,2-, 148 dimethylpropanenitrile, 2,2-, 106, 193 dimethylpropanoic acid, 2,2-, 94, 188, 334 dimethyl-propanol, 2,2-, 258 dimethylpyrazolidine-3,5-dione, 4,4-, 389 dimethylsilaethanol, 2,2-, 261 dimethylsilane, 445 dimethylsulfone, 362 dimethyl-tetrahydrofuran, 2,5-, 78 dimethylurazole, 1,2-, 389 dimethy-p-NO2-benzyl alcohol, 1,1-, 259

1641 dimethypyrrole, 2,5-, 387 dimethy-tocol, DMT, 5,7-, 295 dimeyl-oxathiolane, 2,2-, 129 dineopentyl peroxide, 313 dinitroazoxyfurazan, 4,4-, 357 dinitroazoxyfurazan, 4,4 0 -, 357 dinitrobutane, 1,1-, 110, 201, 298, 410 dinitrodifluoromethane, 409 dinitroethane, 1,1-, 109, 200, 398, 410 dinitroethane, 1,2-, 200 dinitrogen difluororide, (E)-, 397 dinitrogen difluororide, (Z)-, 397 dinitrogen oxide, 347, 396 dinitrogen pentoxide, 348 dinitrogen tetroxide, 348, 396 dinitrogen trioxide, 396 dinitromethane, 110, 409 dinitropentane, 1,1-, 110, 201, 398, 410 dinitropropane, 1,1-, 109, 200, 398, 410 dinitropropane, 2,2-, 200, 410 di-N-oxides, 357 dioctanylphosphine, 482 dioxan-2-yl-peroxy, 316 dioxane, 1,4-, 81 dioxanes, substituted, 1,3-, 79-81 dioxepanes, substituted, 1,3-, 82 dioxolanes, substituted, 1,3-, 78– 79 dioxygen bromide radical, 310 dioxygen fluoride radical, 310 dipentylamine, 103 diphenyl diselenide, 451 diphenyl disulphide, 433 diphenyl ditelluride, 453 diphenyl ether, 331 diphenyl germane, 469 diphenyl hydrazine, 1,2-, 397 diphenyl ketone, 186 diphenyl methyl silamethane, 458 diphenyl silamethane, 458 diphenyl sulfoxide, 362 diphenyl sulphide, 440 diphenyl(phenylamino)amine, substituted, 376 diphenyl-9,10-dihydroanthracene, (E)-9,10-, 61 diphenyl-9,10-dihydroanthracene, (Z)-9,10-, 61 diphenylacetic acid, 188 diphenylacetonitrile, 107 diphenylamine, 9, 384, 415 diphenylamine, substituted, 9, 384, 385 diphenyl-CN-methyl dimer, 196 diphenylethane, 1,1-, 46 diphenylethane, 1,2-, 45 diphenylgermane, substituted, 468 diphenylhydrazine, 1,2-, 384 diphenylmethane, 45 diphenylmethane, substituted, 45 diphenylmethanimine, 373 diphenylmethn-1-ol, 73 diphenylmethyl hydroperoxide, 269 diphenylmethyl methyl ether, substituted, 75 diphenylmethyl methyl ketone, 89 diphenylmethyl phenyl ketone, 90

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1642 diphenylmethyl sulfonyl benzene, 130 diphenylmethylamine, 104 diphenylpropane, 2,2-, 177 diphenylpropane-1,3-dione, 1,3-, 90 diphenylsulfone, 362 diphosphine, 482 dipropyl disulphide, 433 dipropyl ether, 327 dipropyl ketone, 86 dipropyl peroxide, 313 dipropyl sulphide, 440 di-sec-butyl ether, 328 di-sec-butyl peroxide, 313 disilane, 456, 459 disilene, 459 disilicon hexafluoride, 460 disulfur oxide, 361, 432 disulfur, 431 ditertbutyl ether, 74, 328 ditertbutyl peroxide, 313 ditertnonafluorobutyl peroxide, 314 dithianes, substituted, 1,3-, 127 ditrifluoromethyl peroxide, 313 diuret, 374 divinyl ether, 325 DMA–O2 (endoperoxide, 9,10-dimethyl-9, 10-epidioxynthracene), 320 dodecahedrane, 61 dodecane, 153 dodecanethiol, 427 dodecanoic acid, 263 DPA –O2 (endoperoxide, 9,10-diphenyl-9, 10-epidioxyn-thracene), 320

E enol, 70, 260 enols, 260 erythro-2,3-dibromobutane, 174 ethanal, 83, 178, 181 ethanamidine, 375 ethane, 19,147 ethane, substituted, 300, 301, 305 ethane-1,1-diol, 73, 260 ethane-1,2-dial, 73, 186 ethane-1,2-diamine, 105, 372, 414 ethane-1,2-diol, 73 ethanediamine, 1,2-, 198 ethanedisulfur radicals, 444 ethaneperoxycarboxylic acid, 312 ethanethioic S-acid, 438 ethanethiol, 1,2-, 204 ethanethiol, 437 ethanol, 70, 257, 321 ethanolamine, 118 ethene-1-thiol, 426, 437 ethenol, 70, 321 ether, substituted, 301 ethoxy-1,1-dimethyl-1-silaethane, 1-, 344, 462 ethoxy-1-phenylethan-1-one, 2-, 90

Comprehensive Handbook of Chemical Bond Energies ethoxyacetonitrile, 345 ethoxyethyl benzene, 1-, 330 ethyl 2,2,2-tribromoacetate, 242 ethyl 2,2,2-trichloroacetate, 230 ethyl 2,2-dibromoacetate, 242 ethyl 2,2-dichloroacetate, 230 ethyl 2-iodoacetate, 252 ethyl 2-methylpropanoate, 97 ethyl 2-phenylacetate, 97 ethyl 2-phenylpropanoate, 99 ethyl 3-oxobutanoate, 98 ethyl acetate, 251, 335 ethyl aminooate, 373 ethyl azide, 402 ethyl butyl sulphide, 439 ethyl butylanoate, 96 ethyl chloroformate, 335 ethyl dimethylamine, 415 ethyl ethyl disulfonyl dissulfide, 434 ethyl ethylphosphate, 485 ethyl fluorene-9-carboxylate, 100 ethyl furan, 2-, 181 ethyl hydroperoxide, 100, 267, 312, 337 ethyl iso-cyanide, 405 ethyl iso-propyl sulfide, 439 ethyl methyl 2-(1,1-dimethyl-1silaethyl) propane-1,3-dioate, 100 ethyl methyl 2-ethyl propane-1,3-dioate, 99 ethyl methyl butane-1,4-dioate, 97 ethyl methyl disulphide, 441 ethyl methyl ether, 74, 181, 325 ethyl methyl ketone, 86, 184, 185 ethyl methyl propane-1,3-dioate, 96 ethyl methyl sulphide, 204, 438 ethyl methyl sulphone, 442 ethyl methylamine, 414 ethyl nitrate, 343, 351 ethyl nitrite, 342, 349 ethyl nitroperoxy, 351 ethyl octafluoro-fluorene-9-carboxylate, 100 ethyl pentanoate, 96 ethyl peroxy, 339 ethyl phenyl ether, 330 ethyl phenyl ether, substituted, 75 ethyl phenyl ketone, 88, 185 ethyl phenyl sulphide, 204, 440 ethyl propanoate, 96 ethyl propyl ether, 181, 326 ethyl propyl ketone, 184 ethyl propyl sulfide, 439 ethyl radical, 134 ethyl tert-butyl ether, 74 ethyl vinyl ether, 325 ethyl-1H,3H,5H,7H-1,3-oxazolidino-(3,4-C)1, 3-oxazolidine, 7a-, 123 ethyl-1-naphthalene, 165 ethyl-1-pentyne, 2-, 150 ethyl-1-propene, 2-, 28 ethyl-2-aminoacetate, 120 ethyl-2-cyano-2-pentafluoro-phenyl-acetate, 121 ethyl-2-cyano-2-phenyl-acetate, 121

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Index of Compound Names ethyl-2-cyano-2-phenylacetates, substituted, 121 ethyl-2-methyl-pentane, 3-, 151 ethyl-2-methylpropane, 2-, 328 ethyl-3-(dimethylamino) prooanoate, 120 ethyl-3,3-dimethyl-propanol, 2-, 258 ethyl-3-aza-3-diazopro-3-enoate, 405 ethyl-4,4-dimethyl-1,3-oxazolidine, 3-, 122 ethyl-9-anthracene, 165 ethyl-9-phenanthrene, 165 ethylamine, 102, 197, 412 ethylamino acetate, 120 ethylbenzene, 43 ethylbenzene, substituted, 43 ethylbutanal, 2-, 83 ethyl-cyclo-butane, 153 ethyl-cyclo-hexane, 153 ethyl-cyclo-hexyl radical, 1-, 138 ethyl-cyclo-pentane, 153 ethyl-cyclo-pentyl radical, 2-, 138 ethylene glycol, 180 ethylene, 25, 154 ethyl-hexane, 3-, 151 ethylmethylamino methyl-peroxy, 341 ethylnaphthalene, 1-, 51 ethyl-pentanamide, 2-, 373 ethyl-pentane, 3-, 149 ethylphosphine, 481 ethylpyridine, 2-, 197 ethylpyridine, 3-, 197 ethylpyridine, 4-, 197 ethyl-silapentane, 3-, 456 ethylthiol, 203, 426 ethyn-1-ol, 256 ethynol, 321 etrafluoro-1-propanol, 2,2,3,3-, 178

F FeII(H2bim), 394 FII(H2bip), 395 flavins, substituted, 320 fluopropane, 1-, 215 fluopropane, 2-, 215 fluorene, oximes, 274 fluorenes, substituted, 53– 56, 116, 125 fluorenyl trimethylammonium bromide, 105 fluoride hydroperoxide, 310 fluorine dioxide, 365 fluoro peroxy, 365 fluoro-1,1-diiodoethane, 1-, 247 fluoro-1,1-diphenyl-propyl benzene, 3-, 177 fluoro-2-methyl-propane, 2-, 215 fluoro-2-silapro-1-ene, 462 fluoroamine, 422 fluorobenzene, 215 fluorochloroiodomethane, 244 fluoro-cyclo-hexane, 215 fluorodichloroiodomethane, 244 fluoro-eth-1-yl radical, 1-, 141 fluoro-eth-1-yl radical, 2-, 141 fluoroethane, 65, 169, 215

1643 fluoroethlene, 167 fluoroethyne, 166, 213 fluoroformyl fluoride, 216, 361 fluoroiodomethane, 213, 244 fluoromethane, 62, 213 fluoromethyl benzene, 216 fluoromethyl hydroperoxide, 266 fluoromethyl radical, 140 fluoromethylene, 139 fluoronitrooxy, 348 fluoronitrooxy, 350, 365 fluorononane, 176 fluoropene, 1-, 215 fluoropropane, 173, 215 fluoropropane, 2-, 173, 215 fluoropropene, 1-, 68, 215 fluorosilane, 463 fluorosilane-1,1,1-triol, 464 fluorosulfuryldifluoramine, 421 formaldehyde, 83, 342 formaldehyde, halogened, 342 formamide, 373, 413 formic acid phenyl ester, 336 formic acid, 93, 262, 333 formyl cyanide, 192 formyl fluoride, 83, 216 formylthio, 361 furazan N-oxides, substituted, 354 furfurol, 84 furoxans, 354

G galvinol, 304 gema-1,2-diphenylethane, 2-, 468 gema-1-phenylfromtane, 2-, 468 germa-1,3-diphenyl-2-benzylpropane, 2-, 468 germane, 467 germanium bromides, 471 germanium carbide, 471 germanium carbides, 471 germanium chlorides, 470 germanium clusters, 469 germanium dimer, 469 germanium fluorides, 470 germanium iodides, 471 germanium monoxide dimer, 473 germanium oxides, 472 germanium selenide, 473 germanium silicides, 472 germanium sulfides, 473 germanium tellurides, 473 glycine, 119, 187 glycine anhydride, 120 glycine ion, 119 glycolic acid, 94, 189, 335

H halogened cyanide, 404 heptafluoro-propane, 1,1,1,2,2,3,3-, 68

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1644 hepta-fluoropropane, 1,1,1,2,3,3,3-, 68 heptanal, 182, 183 heptane, 22, 148, 149, 150 heptanenitrile, 193, 194 heptanethiol, 1-, 204 heptanoic acid, 188, 263 heptanol, 1-, 179 heptene, 1-, 159 heptyl-2 hydroperoxide, 338 hex-2-yl radical, 135 hexaanoic acid, 263 hexabromoethane, 171 hexachloroethane, 222 hexadecene, 1-, 30 hexadiene, 1,5-, 158 hexafluoro-1,3-butadiene, 1,1,2,3,4,4-, 177 hexafluorobenzene, 215 hexafluoroethane, 214 hexahydro-fluorene, 1,2,3,4,4a,9a-, 56 hexamethyl dilead, 478 hexamethyl disialne, 460 hexamethyl ditin, 474 hexamethyldigermane, 470 hexane, 21, 148, 149 hexanethiol, 1-, 204, 437 hexanitroethane, 1,1,1,2,2,2-, 411 hexanitrothane, 201 hexanoic acid, 188 hexanol, 1-, 179, 323 hexanol, 2-, 323 hexaphenyl disilane, 460 hexaphenyl peroxide, 315 hexene, (E)-2-, 158 hexene, (Z)-2-, 158 hexene, 1-, 28, 158 hexene, 2-, 159 hexyl nitrosothio, 420 hexyl-1 hydroperoxide, 337 hexyl-2 hydroperoxide, 337 hexyl-3 hydroperoxide, 338 hexyne, 1-, 155 HOOO radical, 315 HOS radical, 261 hydantoin, substituted, 388 hydrazine radical, 371 hydrazine, 371, 396 hydrazines, substituted, 377 hydrazinophenyl sulfone, 374 hydrazoic acid, 370 hydro disulphide radicals, 435 hydroanthracen-9-one, 10-, 53 hydrobenzo(b)furan-2-one, 3-, 100 hydrobenzoxazol-2-one, 3-, 391 hydrogen alkyl disulfide, 430 hydrogen alkyl polysulfide, 431 hydrogen azide, 396, 402 hydrogen cyanide, 403 hydrogen disulfide radicals, 430 hydrogen disulfide, 430, 432 hydrogen disulfur, 432 hydrogen methyl disulfide, 430

Comprehensive Handbook of Chemical Bond Energies hydrogen polysulfide, 431 hydrogen sulfide, 425 hydrogen sulfide-d2, 425 hydrogen tetrasulfide, 434 hydrogen trisulfide, 431, 433 hydroimidazole, substituted, 279 hydroind1azol-3-one, 1H-2-, 391 hydrooxy methylsulfonate, 364 hydroperoxide, 266, 310 hydroperoxides, 271 hydroperoxy methyl, 311 hydroperoxy radical, 266, 308, 310 hydroperoxy-2,2-dimethylpropane, 1-, 312 hydroperoxyacetone, 1-, 270 hydroperoxycyclohexan-1-one, 2-, 268 hydroperoxyethanenitrile, 2-, 270 hydroperoxymethan-ol, 269 hydroperoxypropan-ol, 2-, 269 hydrophenyl-methylene cyclohexa-2, 5-dien-1-one, substituted, 4-((4-, 303 hydroxamic acids, substituted, 275-276 hydroxy-1,2,5,6-tetra-hydropyridine, substituted, 1-, 281 hydroxy-1,2,5,6-tetra-hydropyrimidine, substituted, 1-, 281 hydroxy-1,3,4-trichloro cyclo-pentadiene, 1-, 242 hydroxy-1,3,4-trichloro, 1-, 323 hydroxyacetic acid, 2-, 95 hydroxyazobenzene, p-, 417 hydroxydiaza-cyclo-heptane, substituted, 282 hydroxydiphenylamine, 4-, 227, 305 hydroxydiphenylaminyl, 4-, 305, 309 hydroxydiphenylmethane, 4-, 45 hydroxy-diphenylmethanes, 4-, 292, 382 hydroxyethanedithioic acid, 2-, 429 hydroxyfluorene, 297 hydroxyimino ethane, 352 hydroxyimino-1,7,7-trimethylbicyclo(2.2.1)-heptane, 2-, 273 hydroxyimino-2,7-dibromo-fluorenylmethane, 274 hydroxyimino-2-PhSO2-fluorenylmethane, 274 hydroxyind1olin-2-one, substituted, 1-, 282 hydroxyind1olin-3-one, substituted, 1-, 282 hydroxyl radical, 308 hydroxylamine, 261, 352, 373 hydroxylamines, substituted, 274–275 hydroxynaphthalene, substituted, 296 hydroxy-N-piperidine, substituted, 277 hydroxy-phenanthrene, 297 hydroxyphenazine-di-N-oxide, 2-, 359 hydroxyphenylthio)-methylthio)phenyl, substituted, 4-((4-, 303 hydroxy-piperidn-4-one, substituted, 1-, 281 hydroxypropanenitrile, 2-, 118 hydroxy-pyrrolidine, substituted, 1-, 227, 278 hydroxy-tetrahydro-imidazole, 1-, 278 hydroxythiol, 363 hypobromous acid, 256, 367 hypochlorous acid, 256, 365 hypofluorous acid, 255, 365 hypoiodomous acid, 256

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Index of Compound Names hypoiodous acid, 368 hyponitrite, 261

I imidazole, 112, 388 imino phenylaminomethyl phenylamine, 375 iminostilbene, 393 ind1an-2-one, 92 ind1ane, 47 ind1ene, 47 ind1ene, substituted, 47–48 ind1ol-3-ylind1ol-1-ol, 3-, 284 ind1ole, 391 ind1olinol, substituted, 283 ind1ophenol, substituted, 302 iodo peroxy, 368 iodo rioxide, 368 iodo-1-propene, (E)-1-, 248 iodo-1-propene, (Z)-1-, 248 iodo-1-propene, 3-, 248 iodo-2,2-imethylpropane, 1-, 249 iodo-2butanone, 3-, 252 iodo-2-methyl-butane, 2-, 249 iodo-2-methyl-propane, 1-, 248 iodo-2-methylpropane, 2-, 249 iodoacetic acid, 252 iodoacetonitrile, 252 iodo-alkanes, 1-, 249 iodo-alkanes, 2-, 249 iodobenzene, 250 iodobenzenes, substituted, 250 iodo-but-1-nen, 3-, 249 iodo-but-1-nen, 4-, 249 iodobutane, 2-, 249 iodo-cyclo-heptane, 250 iodo-cyclo-hexane, 250 iodo-cyclo-propane, 250 iodoethane, 172, 247 iodoethanenitrile, 2-, 246 iodoethyl benzene, 2-, 251 iodoethylbenzene, 1-, 251 iodoethylene, 247 iodoethyne, 247 iodo-isopropyl benzene, 1-, 251 iodomethane, 64, 246 iodomethyl benzene, 176 iodomethyl methyl ether, 252, 325 iodomethyl methyl sulfide, 252 iodomethyl methyl sulfide, 438 iodomethylthio, 449 iodomonitrooxy, 350, 368 iodonaphthalene, 1-, 251 iodonaphthalene, 2-, 251 iodononafluorobutane, 1-, 248 iodo-prop-1-yne, 3-, 247 iodopropane, 1-, 248 iodopropane, 2-, 249 iodopropanioc acid, 3-, 252 iodosilane, 465 iodosobenzoic acid, 2-, 368

1645 iodothio, 449 iodotrinitromethane, 253 iso-butane, 20, 147 iso-butanoic acid, 262 iso-butene, 27 iso-butyl methyl ketone, 86 iso-butyl nitrine, 343, 349 iso-butyl radical, 135 iso-butyl tert-butyl ether, 329 iso-butylamine, 413 iso-chroman-3-one, 100 isocyanato chloride, 423 isocyanic acid, 261, 370, 404 iso-cyanomethane, 108 iso-pentane, 148 iso-pentanoic acid, 262 iso-propoxyethyl benzene, 1-, 331 iso-propyl acetate, 335 iso-propyl ethyl ketone, 184 iso-propyl hydroperoxide, 268, 312, 337 iso-propyl isocyanide, 405 iso-propyl iso-propyl disulfonyl dissulfide, 434 iso-propyl methyl disulphide, 441 iso-propyl methyl ether, 326 iso-propyl methyl ketone, 86, 184 iso-propyl methyl sulphide, 439, 441 iso-propyl methyl sulphone, 443 iso-propyl nitrate, 343, 351 iso-propyl nitrine, 343 iso-propyl pebtanoate, 97 iso-propyl peroxy, 339 iso-propyl phenyl ketone, 88 iso-propyl radical, 135 iso-propylamine, 102 iso-propylbenzene, 162 iso-propylbenzene, substituted, 44 iso-propylthiol, 426 iso-thiocyanic acid, 370

K ketene, 85 ketenylidene, 181

L lead antimonide, 480, 489 lead bismuthide, 480, 489 lead bromides, 479 lead chlorides, 479 lead dimer, 479 lead dioxide, 480 lead fluoridesm 479 lead iodides, 479 lead monohydride, 478 lead monoxide, 480 lead monoxide dimer, 480 lead selenide, 480 lead sulfides, 480 lead telluride, 480

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1646

M malonic acid dimethyl ester, 98 manganese-oxo cubane complex, 306 mercapto fluoride, 425, 446 mercapto radical, 425 mercaptomethyl radical, 444 metaphosphoric acid, 261 methae-1,1-dicarbonitrile, 107 methane, 8, 19 methane, substituted, 301, 304 methanedifulfide, 432 methanedisulfur radical, 444 methanehydrodifulfide, 432 methanenitrile, 106 methaneperoxycarboxylic acid, 269, 312 methanesulfenic acid, 363, 364, 442 methanesulfonic acid, 364, 442 methanethioic S-acid, 438 methanethiol, 125, 436 methanimine, 370 methanisocynate, 342, 410 methanisothiocyanate, 409, 443 methanol, 70, 256, 321 methoxy methylsulfonate, 364 methoxy-1,1-dimethyl-1-silaethane, 1-, 344 methoxy-1-phenylethan-1-one, 2-, 90 methoxy-1-thiol, 345, 364 methoxy-2-phenylethane-nitrile, 2-, 118 methoxyacetonitrile, 199 methoxyamine, 345, 352 methoxybenzene, 8, 329 methoxyethanenitrile, 2-, 118 methoxyethyl benzene, 1-, 330 methoxygermane, 469 methoxymethylthio, 345, 364 methoxy-N-phenyl-benzenamine, 4-, 380 methoxyphenylacetonitrile, 1-, 44 methoxysulfinyl methoxy, 362 methy-2-phenylpropanal, 2-, 84 methyl disulphide radicals, 435 methyl 2-(dimethylamino)-acetate, 119 methyl 2-chloroacetate, 230 methyl 2-hydroxyacetate, 190 methyl 2-methyl-vinyl ether, 326 methyl 3-cyanopropanoate, 121 methyl acetate, 335 methyl acrylate, 189, 355 methyl aminooate, 373 methyl anthracenyl-9 ketone, 87 methyl azide, 402 methyl benzoate, 97, 190, 336 methyl bytanoate, 97 methyl ester nitrous acid, 199 methyl formate, 95, 333, 335 methyl furan, 2-, 78 methyl hydrazine, 414 methyl hydrodifulfide, 448 methyl hydrodisulfide, 441 methyl hydroperoxide, 100, 266, 311, 337 methyl hydro-peroxide, a-Co2 K-, 270

Comprehensive Handbook of Chemical Bond Energies methyl hydrotrisulfide, 434 methyl hypochlorite, 369 methyl hypofluorite, 365 methyl isocyanide, 405 methyl ketene, 191 methyl methyl disulfonyl, 434 methyl methylphosphate, 484 methyl N-(p-tolylsulfonyl)phenyl-oxosulfoximes, 131 methyl naphthyl-1 ketone, 87 methyl nitrate, 343, 351 methyl nitrite, 342, 349 methyl nitroperoxy, 351 methyl pebtanoate, 96 methyl pent-2-yl radical, 2-, 135 methyl pent-3-yl radical, 3-, 135 methyl pentafluorophenyl ether, 329 methyl pentyl sulphide, 439 methyl peroxy, 338 methyl peroxy, a-NH2-, 341 methyl peroxy, a-OH-, 341 methyl phenol sulphone, 443 methyl phenyl disulphide, 443 methyl phenyl ether, 75 methyl phenyl ketone, 87, 185 methyl phenyl ketone, substituted, 87 methyl phenyl silamethane, 458 methyl phenyl sulphide, 440 methyl phenyl sulphone, 129 methyl p-NO2-phenyl sulphone, 129 methyl propanoic acid, 1-, 93 methyl propyl ether, 326 methyl propyl ketone, 184 methyl propyl sulphide, 204, 438, 439 methyl radical, 134 methyl silane, 455, 460 methyl silane-1,1,1-triol, 461 methyl sulphone radical, 442 methyl tert-butyl disulphide, 441 methyl tert-butyl ketone, 86 methyl tert-butyl sulphone, 443 methyl trifluoromethyl ether, 74 methyl trimethylphenyl ketone, 87 methyl trofluoromethyl sulphone, 129 methyl((methylnitroamino)-methyl)nitroamine, 398, 418 methyl-1,1-dimethyl-1-silaethane, 1-, 462 methyl-1,1-diphenylpropane, 2-, 163 methyl-1,2-propanediamine, 2-, 198 methyl-1,3-dioxanes, 3-, 100 methyl-1,3-dithiolanes, 2,2-, 127 methyl-1,4-pentadiene, 3-, 29 methyl-1-benzylpyridinium bromide, 3-, 117 methyl-1-butanethiol, 2-, 203 methyl-1-butanethiol, 3-, 204 methyl-1-butanol, 2-, 179 methyl-1-butanol, 3-, 179 methyl-1-butene, 2-, 27, 157, 158 methyl-1-butene, 3-, 27, 157, 158 methyl-1-butyne, 3-, 25, 135 methyl-1-hexene, 5-, 160

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Index of Compound Names methyl-1-pentene, 2-, 155, 159 methyl-1-pentene, 3-, 159 methyl-1-pentene, 4-, 159 methyl-1-phenylpropane, 2-, 163 methyl-1-propanethiol, 2-, 203, 437 methyl-1-propanol, 2-, 179, 322 methyl-2,2,2-trifluoroacetate, 189 methyl-2-aminoacetate, 120 methyl-2-butanethiol, 2-, 437 methyl-2-butanol, 2-, 180, 322 methyl-2-butanol, 3-, 180 methyl-2-butene, 3-, 28 methyl-2-nitropropane, 2-, 109, 408 methyl-2-pentene, (E)-4-, 159 methyl-2-pentene, (Z)-4-, 25, 159 methyl-2-pentyne, 4-, 25 methyl-2-phenylpropanenitrile, 2-, 107, 195 methyl-2-phenyl-propionate, 190 methyl-2-propanethiol, 2-, 437 methyl-2-propanol, 2-, 322 methyl-2-propylamine, 2-, 412 methyl-2-silapro-1-ene, 2-, 461 methyl-2-silapropan-2-ol, 2-, 462 methyl-3-pentene, 4-, 29 methyl-9,10-dihydro-acridine, substituted, 10-, 117 methylacenaphthene, 4-, 57 methylacenaphthene, 57 methylallyl radical, 2-, 137 methylamine, 102, 370, 411 methylamino methanethial, 436 methylbenzene, 161 methylbenzo(b)phenanthrene, 60 methylbenzyl radical, a-, 139 methylbenzylamine, 413 methyl-benzylcyanide, a-, 194, 195 methylbutane, 2-, 21, 148 methylbutane, 3-, 147 methylbutanenitrile, 2-, 194 methyl-butanoic acid, 2-, 334 methylbutanoic acid, 3-, 188 methyl-butyl-2 radical, 2-, 135 methylbytanyl nitrine, 2-, 343 methylchrysene, 6-, 60 methyl-cyclo-hexane, 153 methyl-cyclo-hexyl radical, 1-, 138 methyl-cyclopentan-1-ol, 1-, 259 methyl-cyclo-pentane, 153 methyl-cyclo-propane, 31 methylcyclopropene, 1-, 156 methyldiethanolamine, 118 methyldiphenylphosphino-1-thione, 450, 486 methylene, 134 methylene-1,4-dihydronaphthalene, 1-, 50 methylene-6,10,-dihydroanthracene, 9-, 52 methylene-phenathrene, 4,5-, 51 methylethyl amino acetate, 120 methylethyl-1,3-dithiepane, 4-, 128 methylethyl-1,3-dithiocane, 4-, 128 methylheptane, 2-, 151 methylheptane, 3-, 151 methylhexane, 2-, 150

1647 methylhexane, 3-, 22, 150 methylhydrazine radical, 372 methylhydrazine, 112, 372, 397 methylhydroxylamine, 353 methylidyne, 134 methylind1ene, 1-, 164 methylketene, 85 methylmethane-1,1-dicarbonitrile, 108 methylnaphthalene, 1-, 50 methylnaphthalene, 2-, 50 methylnitroamine, 110, 371, 418 methylnitrosothio, 420 methylnonane, 2-, 152 methylnonane, 5-, 152 methyloctane, 3-, 23 methyl-oxirane, 2-, 77, 191 methyloxyethane, 1,2-, 181 methylpentane, 2-, 22, 148, 149, 151 methylpentane, 3-, 22, 148, 149, 151 methylpentane-2,4-dione, 3-, 90 methylphosphine, 481 methylpiperidine, 2-, 197 methylpropan-2-ol, 2-, 71 methylpropanal, 2-, 81, 182 methylpropane-2-disulfur radical, 2-, 444 methylpropanenitrile, 2-, 106, 193, 195 methylpropanoiacid, 2-, 334 methylpropanoyloxy 2-methylpropanoate, 2-, 317 methylpropylamine, 2-, 198 methylpropylbenzene, 2-, 163 methylpyrrile, 1-, 45 methylsulfone, 429 methylthio peroxy, 363 methylthio radical, 436 methylthiocarbonitrile, 443 methylthiol, 426 methylthiyl peroxy, 341, 364 methylvinyl nitroperoxy, 1-, 352 methyoxirane, 2-, 191 methyoxy-1-thiol, 364 monocuclear manganese hydroxide, 307 morpholin-4-yl phenyl ketone, 124 morpholines, substituted, 122

N N-((1E)-buta-1,3-dienyl)-benzamide, 374 N-(4-phenoxy)phenyl-2-naphthalenamine, 380 N-(aminocarbonyl)acetamide, 419 N-(phenylamino)acetamide, 384 N-(tert-butyl)-2,2-dimethyl propanamine, 374 N-(tert-butyl)-N-hydroxy-benzamide, substituted, 276 N-(tert-butyl)-N-hydroxy-carboxamide, substituted, 276 N,N,N 0 N 0 -methyl-methanediamine, 414 N,N 0 -di(4-isopropylphenyl-)-p-phenylendiamine, 386 N,N 0 -di-2naphthyl-p-phenylendiamine, 386 N,N 0 -diphenyl-1,4-phenylene-diamine radical, 382

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1648 N,N 0 -diphenyl-1,4-phenylene-diamine, 382 N,N 0 -methylaniline, 416 N,N-difluorobenzylamine, 411 N,N-difluorohydroxylamine O-fluorosulfate, 352, 364 N,N-dimethylacetamide, 119, 417 N,N-dimethylaniline, substituted, 105 N,N-dimethylformamide, 119, 417, 418 N,N-dimethyl-propanamide, 418 N-[(1E)-1-aza-2-phenylprop-1-enyl]aminoamide, substituted, 376 N-1-(3,7-bis(1,1-dimethyl-ethyl)napthalenyl-benzenamine, 386 NADH, 123 NADHC†, 123 N-alkoxyanilines, 377 naphonyl ethers, substituted, 331 naphth-1-yl hydroperoxide, 270 naphth-2-yl hydroperoxide, 270 naphthalene, 49 naphthalene-1,4-diol, 296 naphthalenethiol, 430 naphthanlenamine, 1-, 371 naphthanlenamine, 2-, 371 naphthlene-1-carboxylic acid, 188 naphthlene-2-carboxylic acid, 189 naphthol, 1-, 324 naphthol, 2-, 324 naphthyl anion, 2-, 49 naphthyl radical, 2-, 50, 139 naphthyl-1 phenyl ketone, 89 naphthyl-2 phenyl ketone, 89 naphthyl-3H-4,5,6,-trihydropyran-2-one, 3-(2-, 100 naphthylamine, 1-, 385, 413 naphthylamine, 2-, 413 naphthylphenylamine, 385 naphthylphenylamines, substituted, 2-, 385 N-benzylaniline, 415 n-butyl radical, 135 n-butylthiol, 426 neo-pentane, 21 neo-pentyl alcohol, 259 neo-pentyl peroxy, 340 N-ethylaniline, 415 N-halogenosuccinimide, 423 n-hexyl radical, 135 N-hydroxyphthalimide (NHPI), 283 N-hydroxyphthalimide (NHPI), substituted, 283 nicotinic acid, substituted, 265 N-iso-propylacetamide, 119 nitrate, 348 nitrates, 344 nitric acid, 261, 350 nitric oxide dimer, 348, 396 nitric oxide, 347 nitric peracid, 351 nitro compounds, 353 nitro(2-(nitrooxy)ethyl)amine, 199, 202, 417 nitro(2-(nitrooxy)ethyl)oxy, 202 nitro(phenylmethoxy) methane, 111 nitro[(nitroamino)methyl]amine, 110, 371, 417 nitro[2-(nitroamino)ethyl]amine, 110, 371, 417

Comprehensive Handbook of Chemical Bond Energies nitro[5-(nitroamino)pentyl]amine, 110, 371, 417 nitroadamantane, 1-, 345 nitroamine, 398 nitrobenzene, 408 nitrobenzene, substituted, 409 nitrobenzyl compounds, 353 nitrobutane, 1-, 109, 200, 408 nitrobutane, 2-, 200, 408 nitro-cyclo-hexane, 110, 408 nitro-cyclo-pentane, 110 nitro-cyclo-propane, 110, 408 nitroethane, 109, 199, 407 nitroethylene, 407 nitrofluoroalkanes, 216 nitrofluoroethanes, 203 nitrofuran, 2-, 411 nitrogen bromofluoride, 423 nitrogen chlorofluoride, 422 nitrogen dioxide, 347 nitrogen iodide, 423 nitrogen monobromide, 423 nitrogen monochloride, 422 nitrogen trifluoride, 422 nitrogen, 395 nitrohexane, 408 nitromethane, 109, 407 nitromethyl radical, 353, 407 nitronaphthalene, 1-, 406 nitropentane, 1-, 109, 200, 408 nitropiperidine, 1-, 354 nitropropane, 1-, 109, 200, 408 nitropropane, 2-, 109, 200, 408 nitro-propylene-2, (E)-, 407 nitroso benzoate, substituted, 352 nitroso formate, substituted, 352 nitroso trimethylsilane, 463 nitroso-10H, 11H-dibenzo(b,f)azepine, 5-, 401 nitroso-1-propene, 3-, 406 nitrosobenzene, 407 nitroso-benzo(b,f)azepine, 5-, 401 nitrosocarbazole, 9-, 401 nitrosodiphenylamine, substituted, 402 nitrosoethane, 406 nitrosoindole, 401 nitrosoindole, substituted, 401 nitrosomethane, 406 nitroso-pentafluorobenzene, 407 nitrosophenoxazine, 10-, 401 nitrosophenyl(phenyl-solfonyl)-amine, substituted, 400 nitroso-propane, 2-, 406 nitrososilane, 463 nitroso-tert-butane, 406 nitrosotoluene, 407 nitroso-trichloromethane, 406 nitroso-trifluoromethane, 406 nitrosyl bromide, 423 nitrosyl chloride, 422 nitrosyl cyanide, 406 nitrosyl fluoride, 422 nitrosyl hydride,348, 370

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Index of Compound Names nitrosyl iodide, 423 nitrothiol, 420 nitrothiomethyl acetate, 420 nitrous acid, 260, 348 nitrozoamines, 111, 202, 398 nitryl bromide, 423 nitryl chloride, 422 nitryl fluoride, 422 nitryl iodide, 423 N-methyl acetamide, 374, 415, 417 N-methylaniline, 415 N-methylglycine, 187 N-methylglycine, 419 N-methyl-nitrosobenzenesulforn-amides, substituted, 390 N-methyl-phenylamine, 380 N-methyoxymethanamine, 353 N-nitrodimethylamine, 398 N-nitromethylamine, 398 N-nitromorpholine, 354 N-nitroso-acetanilides, 399 non-2-ene, (Z)-, 30 nona-1,8-diene, 29 nonane, 152 nonanoic acid, 262 nonanol, 72 nonanyl phenyl ketone, 88 norboradine, 37 norbornane, 36 norcamphor, oximes, 273 n-pentyl radical, 135 N-phenylacetamide, substituted, 381 n-propyl radical, 134 n-propylbenzene, 43

O octane, 23, 149, 150, 151 octane-2-thiol, 426 octanenitrile, 195 octanoic acid, 268 octediene, 1,3-, 29 octene, (E)-2-, 29 octene, 1-, 29, 160 octyl pentanoate, 97 octylphosphine, 481 organoferric species, Fe0, 133 organoferric species, FeI, 133 organoferric species, FeII, 133 organoferric species, FeIII, 134 organomecuer species, 285 oxa-disilapropane, 3-, 462 oxalic acid, 189 oxalic acid dimethyl ester, 97 oxalyl chloride, 186 oxathianes, substituted, 1,3-, 122 oxathiolanes, substituted, 1,3-, 127, 129 oxazolidin-2-one, 1,3-, 388 oxazolidines, substituted, 1,3-, 122

1649 oxazolin-2-one, 1,3-, 387 oxilic axcid diethyl ester, 98 oxime, 272 oximes, 272–273 oximes, substituted, 273, 274 oxirane, 77 oxoacetic acid, 2-, 95 oxomorpholine, 2-, 123 oxopropanedinitrile, 199 oxygen, 309 oxygen deuteride, 255 oxygen tritide, 255 oxyhydrodisulfide, 363 oxyhydrosulfide radicals, 363 oxythio, 428 oxythio radical, 360, 428 ozone, 310

P penta-1,4-dien-3-ol, 72 penta-2,3-diene, 28 pentachloroethane, 66, 170, 222 pentachloroethyl hydroperoxide, 268 pentadiene, (E)-1,3-, 157 pentadiene, (Z)-1,3-, 157 pentadiene, 1,2-, 157 pentadiene, 1,3-, 27 pentadiene, 1,4-, 27, 157 pentadiene, 2,3-, 27, 28 pentadienyl peroxy, 340 pentafluoro-2-iodopropane, 247 pentafluorobenzene, 69 pentafluoro-benznic acid, 188 pentafluoroethane, 64, 168, 218 pentafluoroiodobenzene, 246 pentafluoroiodoethane, 246 pentafluorophenol, 285, 323 pentafluorophenyl acetonitrile, 107 pentafluorophenyl fluorene, 9-, 69 pentafluorophenyl trifluoromethane, 177 pentafluorophenylmethane, 176 pentafluoropropanoic acid methyl ester, 189 pentafluorosulfur difluororamine, 421 pentafluorosulfur trifluoromethane, 443 pentahydroxyhexanal, 2,3,4,5,6-, 85 pentamethyl disilane, 456 pentamethyl-3-silapentane, 2,2,3,4,4-, 457 pentamethylpentane-2-thiol, 2,4,4,6,6-, 457 pentanal, 85, 182, 183 pentane, 21, 147, 148 pentane-2,3-dione, 186 pentane-2,4-dione, 90 pentanedione, 2,4-, 186 pentanenitrile, 147, 148 pentanethiol, 1-, 203, 437 pentanitrofluoroethane, 1,1,1,2,2-, 203, 411 pentanitropropane, 201 pentanoic acid, 188, 262, 334

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1650 pentanol, 1-, 179, 322 pentanol, 2-, 180, 322 pentanol, 3-, 180, 322 pentanoyloxy pentanoate, 317 pentaphenyl-1,4-pentadiene, 1,1,3,5,5-, 46 penten-3-yne, 1-, 25 pentene, (E)-2-, 28, 157 pentene, (Z)-2-, 28, 157 pentene, 1-, 27, 157 pentene, 2-, 157 pentyl tert-butyl ether, 329 pentyl-2 radical, 135 pentylamine, 102 pentyne, 1-, 25 pentyne, 2-, 25, 155 perchloroethane, 170 perfluorinated peroxide, 316, 317 perfluorobutane, 176 perfluoroethane, 168 perfluoropronene, 172 perfluoropropane, 172 permanganic anion, 306 peroxides, substituted, 314, 315 peroxodiphosphate, 319 peroxodisulfate, 319 peroxyacetyl nitrate, 316, 352 peroxydisulfuryl difluoride, 319 peroxynitric acid, 311 phenalene, 59 phenalenyl p-dimer, 165 phenalenyl, substituted, p-dimer, 165 phenalenyl, substituted, s-dimer, 165 phenanthrenylmethane, 9-, 59 phenazine N-oxide, 358 phenol, 285, 323 phenols, di-substituted, 289 phenols, penta-substituted, 292 phenols, substituted, 285, 291, 298– 300 phenols, tetra-substituted, 291 phenothiazine, analogues, 393 phenothioazine, substituted, 393 phenyl hydrotrisulfide, 434 phenyl 2,2-dipiperidylethan-1-one, analogues, 1-, 125 phenyl 2-chloroacetate, 230 phenyl acetate, 336 phenyl azide, 402 phenyl benzoate, 336 phenyl benzyl ether, 331 phenyl dimethylamine, 415 phenyl diphenylmethyl sulphide, 128 phenyl disulphide radicals, 435 phenyl germane, 468 phenyl hydrazine, 414 phenyl hydrodisulfide, 433 phenyl hydroperoxide, substituted, 269 phenyl methyl ketone, 185 phenyl methyl silamethane, substituted, 457 phenyl methyl sulphide, 128 phenyl methylamine, 414 phenyl methylene ketone dibutylsulfonium bromide, 119

Comprehensive Handbook of Chemical Bond Energies phenyl methylene ketone, 131 phenyl nitrite, 350 phenyl nitrosothio, substituted, 420 phenyl phenathrenyl-2 ketone, 89 phenyl phenathrenyl-3 ketone, 89 phenyl phenathrenyl-9 ketone, 89 phenyl phenylsulfonyl sulfate, 363 phenyl phenylsulphonyl methane, substituted, 132 phenyl phenylthiooxy sulfate, 363 phenyl piperazin-2-yl ketones, substituted, 124 phenyl piperidyl ketone, 124 phenyl pyrenyl-1 ketone, 89 phenyl pyridyl ketone, 89 phenyl radical, 40, 139 phenyl silane-1,1,1-triol, 461 phenyl thiophenyl sulfate, 363 phenyl vinyl ether, 330 phenyl(phenylamino)methane-1-thione, 383 phenyl(phenylsulfonyl)-amine, substituted, 376 phenyl, 40, 139 phenyl-1-butene, 4-, 162 phenyl-1-naphthlamine, 380 phenyl-2-(2-pyridyl)-ethanenitrile, 2-, 107 phenyl-2-naphthlamine, 380 phenyl-2-phenoxyethan-1-one, 1-, 90 phenyl-2-phenoxyethane-nitrile, 2-, 118 phenylacetic acid, 2-, 188, 335 phenylacetonitrile, 44, 107 phenylacetylene, 161 phenyl-allyl triphenyl phosphonium bromide, 3-, 30 phenylamine, substituted, 277 phenylaminyl phenoxyl radical, 4-, 382 phenylbutane, 2-, 163 phenylbutane-1,3-dione, 1-, 90 phenyl-cyclo-buten-3-yl radical, 1-, 137 phenyl-cyclo-buten-3-yl, 1-, 32 phenyl-cyclo-butene, 1-, 32 phenyl-cyclo-butene, 1-, 45 phenyl-cyclo-propene, 1-, 44 phenyldiallylamine, 105 phenyldibenzylamine, 104 phenyldiethylamine, 104 phenylethanol, 1-, 72 phenylfluorenyl dimer, 9-, 166 phenylgermane, substituted, 468 phenylhydrazine, 383, 397 phenylhydroxylamine, 380 phenylmethane-1,1-dicarbonitrile, 108 phenylmethane-1-thiol, 204, 428 phenylmethanedithioc acid, 429 phenylmethoxy piperidine, substituted, 332 phenylmethylamine, 198 phenyl-N-(phenylcarbonyl-amino)carboxamide, 375 phenyl-N-benzamide, 383 phenylnitroethanes, substituted, 1-, 111 phenylnitromethane, 409 phenylphenylthioamine, 383 phenylphenylthioamine, substituted, 376 phenylphenylthiodiazene, 421

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Index of Compound Names phenylpro-2-ynoic acid, 3-, 265 phenylpropane, 2-, 45 phenyl-propanenitrile, 2-, 107 phenylpropanone, 3-, 183 phenylpropene, (E)-1-, 44 phenylpyrazolidin-3-one, 1-, 388 phenyl-silaethane, 1-, 457 phenylsulfone, 362 phenylthio-9-methyl-anthracene, 10-, 441 phenylthiomethylanthracene, 9-, 441 phenyl-trimethyl-silane, 133 phenylxanthylium phenoxides, substituted, 333 phone, substituted, 305 phosphine, 481 phosphino fluoride, 483 phosphino silane, 466, 484 phosphinotris(dimethylamino)-1-one, 485 phosphorus bromides, 483 phosphorus chlorides, 482 phosphorus clusters, 482 phosphorus fluorides, 483 phosphorus monosulfide, 485 phosphorus nitride, 484 phosphorus oxides, 484 phosphorus triiodide, 483 phosphoryl bromide, 484 phosphoryl chloride, 484 phosphoryl fluoride, 484 phthalimide, 391 phynel acetate, 336 phynelmethylamine, 104 pinane, (Z)-, 39 piperazine, 115 piperdin-1-ol, substituted, 280–281 piperidine, 113 piperidinol, 280 piperidinol, substituted, 284, 332 piperidione, 2,6-, 390 piperidone, analogues, 2-, 390 polonium dimer, 454 polyols, 324 p-phenyl-endiamines, substituted, 386 proline, 191 prop-1-enyl benzene, 1Z, 163 prop-2-enenitrile, 106 prop-2-enylbenzene, 43 prop-2-ynenitrile, 106 propan-2-ol, 71, 322 propanal chloride, 183 propanal, 85, 182, 183, 322 propanamide, 199, 411 propane, 20, 147 propane-2,2-diol, 260 propane-2-disulfur radical, 444 propanediamine, 1,2-, 198 propanedinitrile, 195 propanedioic acid, 95 propanediol, 1,2-, 180 propanedione, 1,2-, 186 propanenitrile, 106, 192, 194 propanethiol, 1-, 203, 437

1651 propanethiol, 2-, 437 propanoic acid, 187, 190, 262, 334 propanol, 1-, 70, 178, 257 propanol, 2-, 71, 179, 257 propanoyl chloride, 182, 229 propanoyloxy propanoate, 317 propargyl radical, 136 propen-1-ol, 2-, 183, 321 propen-1-yl, 1-, 136 propen-2-yl, 1-, 136 propene, 26, 156 propenenitrile, 2-, 192 propenoic acid, 187, 334 propiolactone, b-, 91 propiolonitrile, 192 propoxyethyl benzene, 1-, 330 propyl hydroperoxide, 337 propyl nitrate, 343, 351 propyl nitrine, 343 propyl nitrite, 1-, 349 propyl nitrite, 342, 349 propyl pebtanoate, 86 propyl phenyl ketone, 88 propyl vinyl ether, 326, 327 propylamine phosphonium bromide, 371 propylamine, 1-, 102, 198, 412 propylamine, 2-, 198, 412 propylbenzene, 43 propyl-cyclo-hexane, 153 propyl-cyclo-pentane, 153 propylene glycol, 1,2-, 180 propylphenyl phenyl ketone, 88 propylthiol, 426 propyne, 24, 154 proyulphosphine, a-CN-, 482 pyenylethanal, 2-, 84 pyrazine, 114 pyrazines, substituted, 197 pyrazole, 113, 388 pyrene, substituted, 297 pyridine iodide, 253 pyridine N-oxides, substituted, 354 pyridine, 113 pyridines, substituted, 114, 196, 197 pyridinol, 3-, 293 pyridinol, HO–pyridinyl, 324 pyridinols, substituted, 3-, 293 pyridium carboxyled species, 265 pyridone, analogues, 2-, 390 pyridone, analogues, 4-, 390 pyridyl pyridine, 2-(2-, 198 pyridylamine, 2-, 413 pyridylamine, 3-, 413 pyridylamine, 4-, 413 pyrimidine, 114 pyrimidinol, 5-, 293 pyrimidinols, substituted, 5-, 293 pyrrole, 112, 387 pyrrolidin-2-yl-peroxy, 341 pyrrolidine, 112 pyrrolidone, 2-, 387

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1652

Q quadricyclane, 37 quinlines, substituted, 115 quinoline N-oxides, substituted, 357 quinolone, analogues, 2-, 392 quinuclidine, 113

R radical dimer, 191 Rh(I), 395 ROOO radical, 316

S sarcosine, 189, 419 sec-butoxyethyl benzene, 1-, 331 sec-butyl alcohol, 71 sec-butyl nitrine, 343, 349 sec-butyl phenyl ketone, 88 sec-butyl radical, 135 sec-butyl tert-butyl ether, 328 selenium bromide, 451 selenium chloride, 451 selenium dimer, 451 selenium fluoride, 451 selenium hydrides, 452 selenium monocarbide, 452 selenium mononitride, 452 selenium monosulfide, 452 selenium monoxide, 452, 486 selenium phosphide, 452 selenophenol, 451 selenotocopherol, all-rac-a-, 294 S-ethyl thioacetate, 443 sikicon radical, 455 silaeth-1-ene, 2-, 461 silaforaldehyde, 463 silaketene, 463 silane, 455 silane, substituted, 302 silane-1,1,1,1-tetraol, 462 silapro-1-ene, 2-, 461 silapropane, 2-, 460 silicon carbides, 460 silicon clusters, 459 silicon monoxide dimer, 466 silicon nitride, 463 silicon oxide, 462 silicon phosphide, 466, 484 silicon selenides, 452, 466 silicon selenides, 466 silicon sulfides, 466 silicon tellurides, 466 silicoorganics, 304 spiro(2.5)-octa-4,6-diene, 38 spirocyclohexyl-4-(spiro-tetrahydrofuran-2)1,2,3,4-tetrahydroquinoline, 2-, 394

Comprehensive Handbook of Chemical Bond Energies spiro-pentane, 34 S-propyl thioacetate, 443 stannane, 473 succinimide, 388 sulfenic acid, 363 sulfide, substituted, 302–303 sulfur bromide, 448 sulfur dibromide, 448 sulfur dichlorides, 447 sulfur difluoride, 445 sulfur dioxide, 360 sulfur fluochloride, 446, 447 sulfur fluoride, 433, 446 sulfur hexafluoride anion, 445 sulfur hexafluoride, 445 sulfur monoxide, 360 sulfur pantafluoride anion, 445 sulfur pantafluoride, 445 sulfur pantafluorobromide, 449 sulfur pantafluorochloride, 447 sulfur peoxide, 315 sulfur tetrafluoride, 445 sulfur tetrafluorochloride, 447 sulfur tetrafluorooxide, 361 sulfur trifluoride, 445 sulfur trioxide, 360 sulfuric acid, 261, 362, 363 sulfurous acid, 361 sulfurul chlorides, 2361, 448 sulfuryl fluoride, 2361 sulfuryl fluorides, 446 sulphuric acid, 362

T t,perp-HOONO, 260 tellunium dimer, 453 tellunium iodide, 453 tellunium monoantimonide, 454 tellunium monoselenide, 452 tellunium monosulfide, 453 tellunium monotelluride, 453 tellunium monoxide, 453 tellurium hydrides, 453 tellurium phosphide, 454, 486 tellurohenol, 453 tert-amyl nitrite, 350 tert-butanamide, 373 tert-butyl 1,1-dimethyl-1-silaethyl peroxide, 315 tert-butyl acetate, 335 tert-butyl alcohol, 180 tert-butyl ethyl ether, 327 tert-butyl ethyl ketone, 185 tert-butyl ethyl sulphide, 439 tert-butyl hydroperoxide, 268, 312, 337 tert-butyl hypobromide, 367 tert-butyl hypochloride, 366 tert-butyl isocyanide, 406 tert-butyl isopropyl ether, 328 tert-butyl methyl ether, 327 tert-butyl methyl ketone, 185

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Index of Compound Names tert-butyl methyl sulphide, 439 tert-butyl nitrine, 343, 350 tert-butyl nitrosothio, 420 tert-butyl peroxy, 340 tert-butyl phenyl ketone, 88 tert-butyl radical, 135 tert-butyl tert-butyl disulfonyl dissulfide, 434 tert-butyl-2-(3-(tert-butyl)-2-hydroxyphenyl) phenyl, 6-, 181 tert-butyl-2,2,4,4-tetramethyl-3-silapentane, 3-, 457 tert-butyl-2,2-dimethylpro-panoate, 97 tert-butyl-2-aminopropanoate, 121 tert-butylamine, 370 tert-butylbenzene, 44 tert-butylbi-cyclo(1.1.1)-pentane, 3-, 34 tert-butyldifluoroamine, 411 tert-butyldimethylamin, 104 tert-butylperoxide, 338 tert-butyl-tert-amyl peroxide, 313 tert-butylthiol, 426 tert-buytl phenylthioamine, 375 tetrabromomethane, 235 tetrabromosilane, 465 tetrachloro-2,2-difluoroethane, 1,1,1,2-, 170 tetrachlorodiphosphine, 483 tetrachloroditin, 474 tetrachloro-eth-1-yl radical, 1,1,2,2-, 141 tetrachloroethane, 1,1,1,2-, 170, 222 tetrachloroethane, 1,1,2,2-, 66, 171 tetrachloroethyl hydroperoxide, 1,1,2,2-, 268 tetrachloroethylene, 167, 221 tetrachloromethane, 219 tetrachlorosilane, 464 tetradialkyl disulfide ions, 435 tetraethyl benzene, 1,2,2,2-, 241 tetraethyllead, 479 tetrafluobenzene, 1,2,3,4-, 69 tetrafluobenzyl, 1,2,3,4-, 69 tetrafluorodiphosphine, 482 tetrafluoro-eth-1-yl radical, 1,1,2,2-, 141 tetrafluoroethane, 1,1,1,2-, 168, 214 tetrafluoroethane, 1,1,2,2-, 64, 169, 214 tetrafluoroethylene, 166, 214 tetrafluorohydrazine, 397 tetrafluoromethane, 211 tetrafluorosilane, 464 tetrahydroacenaphthene, 57 tetrahydrofuran, 78 tetrahydrofuran-2-yl-peroxy, 316 tetrahydrofurans, substituted, 78–79 tetrahydropyrene, 1,2,3,6-, 60, 82 tetrahydropyridazine-3,6-dione, 1,2,4,5-, 391 tetrahydroquinoline, substituted, 296 tetrahydroxypentanal, 2,3,4,5-, 85 tetraiododiphosphine, 483 tetraiodomethane, 64, 246 tetraiodosilane, 465 tetralin, 48 tetramethyl disilane, 1,1,2,2-, 456 tetramethyl-2-silabutane, 2,2,3,3-, 133 tetramethyl-2-stanna-butane, 2,2,3,3-, 476

1653 tetramethyl-4-oxa-3,5-disilapentane, 2,2,6,6-, 462 tetramethylbutane, 2,2,3,3-, 152 tetramethylbutanedinitrile, 195 tetramethylead, 478 tetramethylethane-1,2-carbonitrile, 1,1,2,2-, 107 tetramethyl-ethanol, 1,1,2,2-, 258 tetramethylhydrazine, 397 tetramethylpentane, 2,2,3,3-, 152 tetramethylpiperidine, 2,2,6,6-, 389 tetramethyl-propanol, 2,2,3,3-, 258 tetramethylsilane, 461 tetramethypentane, 2,2,4,4-, 153 tetranitrobutane, 2,2,3,3-, 201 tetra-nitromethane, 411 tetraoxaspiro[5,5]undecane, substituted, 82 tetraphenyl-1,4-digermin, 2,3,5,6-, 469 tetraphenylethane, 1,1,2,2-, 164 tetraphenylethane, 1,2,2,2-, 164 tetraphenylmethane, 164 tetraphenylpropene, 1,1,3,3-, 46 tetrasilane, 460 thallium bismuthide, 492 thallium phosphide, 486 thian-1-one, 362 thiane-1,1-dione, 362 thiazyl difluoride, 420 thiazyl fluoride, 420 thiazyl fluorides, 420 thiazyl trifluoride, 446 thiazyl, 421 thioacetic acid, 429 thiobenzoic acid, 429 thiocyanogen, 421 thiocynic acid, 431 thioformaldehyde, 125, 436 thioformyl cyanide, 192 thionyl chloride, 447 thionyl fluorides, 446 thiophene iodide, 253 thiourea, 372 thioxanthene, 53 thio-a-tocopherol, 430 thiphenylmethane, substituted, 46 thiphenylmethylium phenoxides, substituted, 333 threo-2,3-dibromobutane, 175 tin bismuthides, 351, 477 tin bromides, 475 tin chlorides, 475 tin clusters, 350 tin dimer, 474 tin fluorides, 475 tin germanides, 474, 475 tin iodides, 476 tin monohydride, 473 tin monoxide dimer, 478 tin oxides, 477 tin selenide, 477 tin sulfides, 477 tin telluride, 478 tocopherol, a-, 9, 294

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1654 tocopherol, b-, 9, 294 tocopherol, d-, 9, 294 tocopherol, g-, 9, 294 toluene bromide, 41 toluene, 43 toluene, di-substituted, 42 toluene, hydridopenta-, 42 toluene, multi-substituted, 41 toluene, other-substituted, 42 toluene, substituted, 41–43 trans-bromonitrooxy, 349 trans-chloronitrooxy, 349 trans-nitrous acid, 348 trant-perp-peronitrous acid, 311 tri(1,1-dimethyl-1-silaethyl)-amine, 463 tri(2,3,5,6-tetrafluoro-phenyl)phenyl methane, 69 triacetylene, 25 trialkyl-N-oxides, 353 triallylamine, 104 triaryl nitrosothio, 420 tribenzylamine, 105 tribromoacetic acid, 2,2,2-, 242 tribromochloromethane, 219, 235 tribromoethane, 111-, 171 tribromofluoromethane, 213 tribromoiodomethane, 245 tribromomethane, 63, 235 tribromomethyl hydroperoxide, 267 tribromophosphino-1-thione, 450, 485 tribromopropane, 1,1,1-, 238 tribromosilane, 459 tributylamine, 104 tributylhosphino-1-thione, 450, 485 tributylstannane, 474 trichloro-1,2,2-trifluoro-ethane, 1,1,2-, 169 trichloro-2,2,2-tri-fluoro ethane, 1,1,1-, 222 trichloroacetaldehyde, 181 trichloroacetic acid, 187 trichloroacetic acid, 2,2,2-, 230 trichloroacetyl chloride, 182 trichloro-eth-1-yl radical, 1,1,2-, 141 trichloro-eth-1-yl radical, 1,2,2-, 142 trichloroethane, 1,1,1-, 170, 222 trichloroethane, 1,1,2-, 171 trichloroethanenitrile, 2,2,2-, 228 trichloroethlene, 167 trichloroethylene, 1,1,2-, 221 trichlorofluoromethane, 212, 218 trichloroiodomethane, 245 trichloromethane, 63, 219 trichloromethyl hydroperoxide, 266 trichloromethyl benzene, 176, 228 trichloromethyl nitroperoxy, 351 trichloromethyl peroxy, 339 trichloro-phenyl methane, 227 trichlorophosphino-1-thione, 449, 485 trichlorosilane, 459 tricyclohexylphino-1-thione, 450, 485 triethanolamine, 118 triethyl germane, 467 triethylamine, 103

Comprehensive Handbook of Chemical Bond Energies trifluoro-1,1-diphenyl-ethyl benzene, 2,2,2-, 177 trifluoro-1-phenyl-ethyl benzene, 2,2,2-, 177 trifluoro-1-propanol, 3,3,3-, 178 trifluoro-2,2-2-trichloroethane, 1,1,1-, 168 trifluoro-2-chloroethyl hydroperoxide, 1,1,1-, 267 trifluoro-2-iodoethane, 1,1,1-, 168, 246 trifluoroacetadehyde, 86 trifluoroacetic acid, 187, 262 trifluoroacetone, 1,1,1-, 86 trifluoroacetonitrile, 192 trifluorobromomethane, 212 trifluorochloroethane, 1,1,2-, 169 trifluoro-eth-1-yl radical, 1,1,2-, 141 trifluoro-eth-1-yl radical, 1,2,2-, 142 trifluoroethan-1-ol, 2,2,2-, 257 trifluoroethane, 1,1,1-, 65, 169, 214 trifluoroethane, 1,1,2-, 169, 214 trifluoroethane, 1,2,2-, 65 trifluoroethanol, 2,2,2-, 178, 321 trifluoroethlene, 167 trifluoroethyl benzene, 2,2,2-, 177 trifluoroethylene, 67 trifluoroiodomethane, 244 trifluoromethane, 61, 211, 244 trifluoromethanol, 256, 321 trifluoromethoxy-trifluoro-methyl peroxide, 316 trifluoromethyl benzene, 176 trifluoromethyl hydroperoxide, 266, 312 trifluoromethyl hypochlorite, 342, 366 trifluoromethyl hypofluorite, 365 trifluoromethyl nitroperoxy, 351 trifluoromethyl peroxy, 338 trifluoromethyl phenyl ketone, 185 trifluoromethyl silane, 461 trifluoromethylhypofluorite, 321 trifluoro-N-phenyl-acetamide, 2,2,2-, 383 trifluorophosphino-1-thione, 449, 485 trifluoroprop-1-yne, 3,3,3-, 172 trifluoropropene, 3,3,3-, 172 trifluorosilane, 459 trihydroacenaphthene, 3,4,5-, 56 trihydropyrimidine-2,4,6-trione, 1,3,5-, 125 triiodofluoromethane, 213 triiodomethane, 246 tri-iso-propanolamine, 118 tri-iso-propylamine, 103 triisopropylthiosilamethane, 457 trimethyl allylsilane, 461 trimethyl bicyclo(2.2.1) heptane-2-one, 1,7,7-, 91 trimethyl bromosilane, 465 trimethyl chlorosilane, 464 trimethyl fluorosilane, 464 trimethyl iodosilane, 465 trimethyl morpholin-2-one, 4,5,5-, 123 trimethyl sulfur pantafluoride, 446 trimethyl sulfur trifluoride, 446 trimethyl-1-(phenylfonyl)-2-silaethane, 2,2,2-, 131 trimethyl-1,2,3,4-tetrahydroquinoline, 2,2,4-, 392 trimethyl-1-pentene, 2,4,4-, 160 trimethyl-2-stanna-butane, 2,2,3-, 476 trimethylamine, 103, 415

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Index of Compound Names trimethylbutane, 2,2,3-, 150 trimethylchlorogermane, 470 trimethylgermane, 467 trimethylhexane, 2,2,5-, 23, 152 trimethylhosphino-1-thione, 450, 485 trimethylpenane, 2,2,3-, 151 trimethylpenane, 2,3,3-, 151 trimethylpentane, 2,2,4-, 23, 152 trimethylpentane, 2,3-, 152 trimethylpentane, 2,3,4-, 152 trimethyl-propanol, 2,3,3-, 258 trimethylsilane, 456, 461 trimethylstannane, 474 trimethylstannane, substituted, 475, 476, 477 trimethyltetralin, 1,5,7-, 48 trimethylthiosilamethane, 457 trinitrobromomethane, 410 trinitrobutane, 1,1,1-, 201, 411 trinitrochloromethane, 410 trinitroethane, 1,1,1-, 201, 410 trinitrofluoromethane, 410 trinitromethancyanide, 201 trinitromethane, 111, 410 trinitropentane, 1,1,1-, 410 trinitropropane, 1,1,1-, 201, 410 trioxocane, 1,3,6-, 83 trioxygen bromide radical, 315 triphenyl germane, 469 triphenyl silamethane, substituted, 459 triphenyl-1-(phenylfonyl)-2-silaethane, 2,2,2-, 131 triphenylene radical cation, 59 triphenylgermane, substituted, 470, 471, 472 triphenylimidazole, 2,4,5-, 389 triphenylmethane, 46 triphenylmethylium phenoxides, 333 triphenylphosphino-1-one, 485 triphenylphosphino-1-thione, 450, 486 triphenylstannane, 474 triphenylstannane, substituted, 475, 477 tripropylamine, 103 trisilane, 459 trisulfur, 431 tri-tert-butyl germane, 467 trithiane, 1,3,5-, 128 tropolone, 260

1655 tropylium phenoxides, substituted, 332 tropylium thiophenoxides, substituted, 441 tungsten alkoxide, 345

U ubiquinol-10, 295 ubiquinol-2, 295 ubiquinol-6, 295 uracil, 124, 375 urazole, 4-substituted, 389 urea, 372

V valerolactone, d-, 100 vinoxy peroxy, 341 vinyl acetate, 336 vinyl alcohol, 256 vinyl bromide, 236 vinyl chloride, 221 vinyl fluoride, 215 vinyl peroxy, 339 vinyl radical, 136 vinylbenzene, 43 vinyl-cyclo-hexane, 161

W water, 255

X xanthene, substituted, 52

Y ylide bromides, 132–133

Z zeroane, 312, 341

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