Compound Bond Dissociation Enthalpy (kcal/mol) Bond (C-Y) Energy Theory Level R = H C-H 79.5 R = Me3C 79.4 R = Ph3C 77.2 R = Me3Si 82.5 R = Et3Si 81.2 R = Ph3Si 80.6 R = PhSO2CH4 99 R = PhSO2CH2SiMe3 99.4 R = PhSO2CH2SiPh3 97.4 R = PhSO2CH(SiMe3)2 96.5 R = PhS(O)(=NSO2Tol)CH3 103.1 R = PhS(O)(=NSO2Tol)CH(SiMe3)2 99.8 R = PhSO2CH2Ph 90.2 R = PhSO2CH(CH=CH2)(SiMe3) 91.1 Zhang, S.; Zhang, X-M.; Bordwell, F. G. J. Am. Chem. Soc. 1995, 117, 602-606. R = PhCH2 C-H heterol. 64.2 homolysis 67.9 R = 4-CH3OPh heterolysis 66.9 homolysis 69.4 R = 4-CH3Ph heterolysis 67.5 homolysis 69.2 R = Ph heterolysis 68.8 homolysis 69.2 R = 4-ClPh heterolysis 70.2 homolysis 69.1 R = 4-BrPh heterolysis 70.4 homolysis 69.2 R = 4-CF3Ph heterolysis 72.6 homolysis 69.5 R = H C-H heterol. 69.3 homolysis 69.4 R = CH3 heterolysis 69.9 homolysis 68.8 R = CH3 C-H heterol. 81.1 homolysis 73.7 Chem. Eur. J. 2003, 9(4) , 871-880 H R N H H R CONH 2 N H H R CO 2 Et EtO 2 C H 3 C CH 3 N H H R
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Compound Bond Dissociation Enthalpy (kcal/mol) Bond (C-Y ...lectka.chemistry.jhu.edu/assets/Bond-Strength-Files/C-H-bond-str.pdfR = 4-CH 3OPh heterolysis 66.9 homolysis 69.4 R = 4-CH
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Compound Bond Dissociation Enthalpy (kcal/mol)Bond (C-Y) Energy Theory Level
Senosiain, J. P.; Han, J. H.; Musgrave, C. B.; Golden, D. M. Faraday Discuss. 2001, 119 , 173-189Reference includes radical stabilization energies
H
MeH
Me
H
H
H
H
H
H
H
H
H
H
Me Me
MeH
Compound Bond Dissociation Enthalpy (kJ/mol)Bond (C-Y) Energy Theory Level
296.6 B3LYP308.8 KMLYP305.4 Experimental
462.3 B3LYP474.0 KMLYP473.1 Experimental
361.7 B3LYP371.8 KMLYP375.7 Experimental
Senosiain, J. P.; Han, J. H.; Musgrave, C. B.; Golden, D. M. Faraday Discuss. 2001, 119 , 173-189Reference includes radical stabilization energies (kJ/mol)
C-H 438.9 Experimental429.7 Estimated
423 Experimental420.7 Estimated
374 Experimental365.6 Estimated
420 Experimental416.7 Estimated
412.5 Experimental411.6 Estimated
364.8 Experimental364.1 Estimated
358.2 Experimental349.0 Estimated
358.2 Experimental347.1 Estimated
410.9 Experimental414.8 Estimated
403.8 Experimental402.6 Estimated
392.9 Experimental386.0 Estimated
386 Experimental396.5 Estimated
387 Experimental392.2 Estimated
Cherkasov, A.; Jonsson, M. J. Chem. Inf. Comput. Sci. 2000, 40, 1222-1226
H
H
H
MeH
H
MeH
HMe
Me
H
H
Me
HMe
Me
HMe
MeMe
NCH
Me NHH
Me NH
Me
CH3H
MeH
Me
Compound Bond Dissociation Enthalpy (kJ/mol)Bond (C-Y) Energy Theory Level
C-H 394.6 Experimental404.6 Estimated
370.3 Experimental381.9 Estimated
357.3 Experimental372.8 Estimated
353.1 Experimental363.8 Estimated
376.1 Experimental377.0 Estimated
361.9 Experimental367.9 Estimated
392.9 Experimental390.4 Estimated
384.9 Experimental387.4 Estimated
446.4 Experimental441.9 Estimated
361.9 Experimental350.7 Estimated
347.7 Experimental356.6 Estimated
403.8 Experimental407.5 Estimated
345.2 Experimental341.7 Estimated
347 Experimental335.8 Estimated
319.7 Experimental330.0 Estimated
365.3 Experimental355.1 Estimated
Cherkasov, A.; Jonsson, M. J. Chem. Inf. Comput. Sci. 2000, 40, 1222-1226
HO
H
Me
H
H
MeMe
NCH
Me
NCMe
MeH
HSH
Me SH
F3C H
H
Me
HH
H
HMe
H
H
MeMe
H
Compound Bond Dissociation Enthalpy (kJ/mol)Bond (C-Y) Energy Theory Level
C-H 338.9 Experimental347.6 Estimated
323 Experimental332.6 Estimated
403.5 Experimental404.1 Estimated
418 Experimental408.8 Estimated
404 Experimental398.6 Estimated
344.3 Experimental346.0 Estimated
326.4 Experimental342.1 Estimated
319.2 Experimental329.0 Estimated
340.6 Experimental334.1 Estimated
339 Experimental325.0 Estimated
411.3 Experimental401.0 Estimated
386.2 Experimental392.0 Estimated
389 Experimental396.1 Estimated
383.7 Experimental382.8 Estimated
401.9 Experimental400.6 Estimated
389 Experimental391.6 Estimated
Cherkasov, A.; Jonsson, M. J. Chem. Inf. Comput. Sci. 2000, 40, 1222-1226
HMe
MeH
MeMe H
H
Me
MeMe
H
Me
Me
MeH
MeMe
MeH
Me
Me
Me
H
Me
MeMe
H
H
HMe
O
MeH
Me OH
O
MeH
Me
OH
Me
Me
HHO
HHO
Me
Compound Bond Dissociation Enthalpy (kJ/mol)Bond (C-Y) Energy Theory Level
C-H 381 Experimental382.6 Estimated
423.8 Experimental433.8 Estimated
431.8 Experimental437.9 Estimated
421.7 Experimental424.4 Estimated
421.3 Experimental428.4 Estimated
413.8 Experimental415.0 Estimated
421.7 Experimental420.3 Estimated
411.7 Experimental410.9 Estimated
392.5 Experimental401.5 Estimated
425.1 Experimental421.4 Estimated
417.2 Experimental413.1 Estimated
401.7 Experimental404.9 Estimated
431 Experimental430.5 Estimated
431 Experimental431.3 Estimated
416.3 Experimental428.8 Estimated
429.7 Experimental432.3 Estimated
Cherkasov, A.; Jonsson, M. J. Chem. Inf. Comput. Sci. 2000, 40, 1222-1226
HHO
Me Me
HF
H H
HF
F H
HF
Cl H
HF
F Cl
HF
Cl Cl
HH
Cl H
HCl
Cl H
HCl
Cl Cl
HBr
H H
HBr
Br H
HBr
Br Br
HI
H H
HI
I H
HMe
F F
HF3C
F F
Compound Bond Dissociation Enthalpy (kJ/mol)Bond (C-Y) Energy Theory Level
C-H 425.9 Experimental414.8 Estimated
393 Experimental393.1 Estimated
397 Experimental388.7 Estimated
404.2 Experimental406.2 Estimated
435 Experimental429.2 Estimated
433.5 Experimental422.7 Estimated
415.1 Experimental415.1 Estimated
383.7 Experimental390.3 Estimated
407 Experimental394.9 Estimated
388 Experimental400.8 Estimated
388 Experimental386.4 Estimated
384 Experimental395.4 Estimated
385 Experimental381.2 Estimated
385 Experimental374.3 Estimated
389 Experimental374.5 Estimated
377 Experimental383.8 Estimated
Cherkasov, A.; Jonsson, M. J. Chem. Inf. Comput. Sci. 2000, 40, 1222-1226
HF3C
Cl H
H
ClCl
H
ClCl
H
ClCl
Cl
ClCl
H
ClBr
F
FF
HF F
FF
F
FF
FF F
HF
F
FF
SiMe
MeMe
H
O
Me H
Me
O
HOH
H2NH
H2NH
MeMe
H2NH
Me
NH
H
NH
HN
H
NH
O
H
HN H
Compound Bond Dissociation Enthalpy (kJ/mol)Bond (C-Y) Energy Theory Level
C-H 416.6 ab-initio422.6 Experimental
370.7 ab-initio375.9 Experimental
419.4 ab-initio423.1 Experimental
405.2 ab-initio406.6 Experimental
375.4 ab-initio375.4 Experimental
426 ab-initio
397.8 ab-initio390.6 Experimental
378.0 ab-initio365.1 Experimental
407.3 ab-initio
375.8 ab-initio365.4 Experimental
419.4 ab-initio423.3 Experimental
407.8 ab-initio409.1 Experimental
371.5 ab-initio371.2 Experimental
Seetula, J. A. J. Chem. Soc Faraday Trans. 1998, 94 , 891-898
H3CH
H3C CH3
Cl
H
MeH
Cl
H3CCl
H
Cl
Cl
CH3
Cl
Cl
Cl
Cl
H
Cl
Cl
MeH
HMe
Me
MeCH3
MeH
ClCl
Compound Bond Dissociation Enthalpy (kJ/mol)Bond (C-Y) Energy Theory Level
C-H 418.7 ab-initio
406.5 ab-initio409.3 Experimental
407.0 ab-initio407.0 Experimental
345.3 ab-initio354.5 Experimental
376.5 ab-initio371.4 Experimental
378.2 ab-initio370.4 Experimental
420.0 ab-initio
401.5 ab-initio
347.8 ab-initio352.9 Experimental
376.3 ab-initio367.5 Experimental
Seetula, J. A. J. Chem. Soc Faraday Trans. 1998, 94 , 891-898
C-H 357
453.5
359.9 ± 20
Ling, Y.; Lifshitz, C. J. Mass Spec. 1997, 32 , 1219-1225
Cl
H
Cl
H
Me
MeH
Cl
MeCl
H3CCl
MeH
Cl
HCl
Me Me
ClMe
Me
H3CCl
Me
H
H
H
MeCl
Compound Bond Dissociation Enthalpy (kcal/mol)Bond (C-Y) Energy Theory Level
C-H 112.3 DFT-AM1102.0, 102.2 Experimental
108.0 DFT-AM198.0, 98.3 Experimental
105.2 DFT-AM195.0, 95.7 Experimental
102.3 DFT-AM192.0, 93.1 Experimental
139.0 DFT-AM1125.0, 126.4 Experimental
120.0 DFT-AM1108.0, 109.2 Experimental
91.3 DFT-AM186.6, 83.1 Experimental
94.1 DFT-AM187.9, 85.6 Experimental
99.6 DFT-AM189.0, 90.6 Experimental
115.7 DFT-AM1106.3, 105.2 Experimental
104.1 DFT-AM196.5, 94.7 Experimental
100.6 DFT-AM194.5, 91.5 Experimental
105.2 DFT-AM195.5, 95.7 Experimental
103.5 DFT-AM192.5, 94.2 Experimental
86.4 DFT-AM181.2, 78.6 Experimental
117.7 DFT-AM1110.2, 107.1 Experimental
Jursic, B. S. J. Chem. Soc. Perkin Trans. 1999, 2 , 369-372
H3C H
HMe
MeMe
H
H
H
NCH
H
H
H
H
H
H
H
HMe
HMe
Me
HH
Compound Bond Dissociation Enthalpy (kcal/mol)Bond (C-Y) Energy Theory Level
C-H 133.0 DFT-AM1120.0, 121.0 Experimental
99.0 DFT-AM187.0, 90.1 Experimental
98.8 DFT-AM186.0, 89.9 Experimental
102.4 DFT-AM193.0, 93.2 Experimental
Jursic, B. S. J. Chem. Soc. Perkin Trans. 1999, 2 , 369-372
C-H 83.3 Calculated85.6 Experimental
79.9 Calculated78.9 Experimental
88.3 Calculated
84.6 Calculated86.6 Experimental
Glasovac, Z.; Eckert-Maksic, M.; Dacres, J. E.; Kass, S. R. J. Chem. Soc. Perkin Trans. 2 2002, 2 , 410-415
C-H 79.4 HF100.3 MP2105.8 B3LYP
104.7, 104.9 Experimental
76.8 HF98.9 MP2101.1 B3LYP
100.2, 101.1 Experimental
74.5 HF95.3 MP297.1 B3LYP
99.4, 98.6 Experimental
72.7 HF93.7 MP294.0 B3LYP
95.2, 96.5 Experimental
77.8 HF96.0 MP299.1 B3LYP101.7 Experimental Avg
Korth, H.-G.; Sicking, W. J. Chem. Soc. Perkin Trans. 2 1997, 715-719
NC H
HO
Me OH
H
H
H
H
H3C H
HMe
Me
HMe
Me Me
FH2C H
HO
Me
MeH
Compound Bond Dissociation Enthalpy (kcal/mol)Bond (C-Y) Energy Theory Level