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T3: Bond Energies

  • Page ID
    10929
  • The following tables list experimental bond dissociation enthalpies of common bonds at 298 K.

    R-H bonds

    Bond \(\Delta{H_{298
    }}\)(kcal.mol-1)
    \(\Delta{H_{298
    }}\)
    (kJ.mol-1)
      Bond \(\Delta{H_{298
    }}\)
    (kcal.mol-1)
    \(\Delta{H_{298
    }}\)
    (kJ.mol-1)
    Inorganics
    H-H 104.2 436.0   H-OH 118.8 497.1
    H-F 136.3 570.3   H-SH 91.2 381.6
    H-Cl 103.2 431.8   H-NO 49.5 207.1
    H-Br 87.5 366.1   H-ONO (trans) 79.1 331.0
    H-I 71.3 298.3   H-ONO2 101.7 425.5
    H-CN 126.3 528.4   H-SiH3 91.7 383.7
    H-NH2 107.6 450.2   H-GeH3 83 347
    Hydrocarbons
    CH3-H 105.0 439.3   C6H5-H 112.9 472.4
    CH3CH2-H 101.1 423.0   C6H5CH2-H 89.8 375.7
    (CH3)2CH-H 98.6 412.5   C5H5-H 79.9 334.3
    CH3CH2(CH3)CH-H 98.2 410.9   c-C3H5-H 105.7 442.2
    (CH3)3C-H 96.5 403.8   c-C4H7-H 95.6 400.0
    CH2CH-H 110.7 463.2   c-C5H9-H 93.0 389.1
    CH2CHCH2-H 88.8 371.5   c-C6H11-H 95.6 400.0
    (CH2CH)2CH-H 76.4 319.7   c-C7H13-H 93.4 390.8
    HCC-H 133.3 557.7        
    Halides
    H-CH2F 101.3 423.8   H-CF3 106.7 446.4
    H-CH2Cl 99.5 416.3   H-CCl3 95.8 400.8
    H-CH2Br 101.6 425.1   H-CBr3 96.0 401.7
    Alcohols
    CH3O-H 104.6 437.6   (CH3)2CHO-H 105.7 442.2
    H-CH2OH 96.1 402.1   (CH3)3CO-H 106.3 444.8
    CH3CH2O-H 104.7 438.1   C6H5O-H 90 377
    Peroxides
    HOO-H 87.8 367.4   CH3CH2OO-H 85 356
    CH3OO-H 88 368   (CH3)3COO-H 84 351
    Carbonyls
    HC(O)-H 88.1 368.6   HCOO-H 112 469
    CH3C(O)-H 89.4 374.0   H-COOH ≥96 402
    H-CH2CHO 94 393   CH3COO-H 112 469
    C6H5C(O)-H 88.9 372.0   H-CH2COOH 96 402
            C6H5COO-H 111 464
    Other
    CH3S-H 87.4 365.7   H-CH2NH2 92.2 385.8
    H-CH2SH 94 393   H-CH2CN 93.4 390.8
    H-CH2SO2Me 99.0 414.2        

     

    1. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255.
    2. Feng, Y.; Huang, H.; Liu, L.; Guo, Q.-X. Phys. Chem. Chem. Phys. 2003, 5, 685.
    3. Zavitsas, A. A. J. Phys. Chem. A 2003, 107, 897.
    4. McGivern, S. W.; Derecskei-Kovacs, A.; North, S. W.; Francisco, J. S. J. Phys Chem. A 2000, 104, 436.
    5. Jursic, B. S. J. Chem. Soc. Perkin Trans. 1999, 2, 369.
    6. Verevkin, S. P.; Krashnykh, E. L.; Wright, J. S. Phys. Chem. Chem. Phys. 2003, 5, 2605.

     

    Single Bonds

    ΔH°*

    Single Bonds

    ΔH°*

    Multiple Bonds

    ΔH°*

    H–H

    104.2

    B–F

    150

    C=C

    146

    C–C

    83

    B–O

    125

    N=N

    109

    N–N

    38.4

    C–N

    73

    O=O

    119

    O–O

    35

    N–CO

    86

    C=N

    147

    F–F

    36.6

    C–O

    85.5

    C=O (CO2)

    192

    Si–Si

    52

    O–CO

    110

    C=O (aldehyde)

    177

    P–P

    50

    C–S

    65

    C=O (ketone)

    178

    S–S

    54

    C–F

    116

    C=O (ester)

    179

    Cl–Cl

    58

    C–Cl

    81

    C=O (amide)

    179

    Br–Br

    46

    C–Br

    68

    C=O (halide)

    177

    I–I

    36.

    C–I

    51

    C=S (CS2)

    138

    H–C

    99

    C–B

    90

    N=O (HONO)

    143

    H–N

    93

    C–Si

    76

    P=O (POCl3)

    110

    H–O

    111

    C–P

    70

    P=S (PSCl3)

    70

    H–F

    135

    N–O

    55

    S=O (SO2)

    128

    H–Cl

    103

    S–O

    87

    S=O (DMSO)

    93

    H–Br

    87.5

    Si–F

    135

    P=P

    84

    H–I

    71

    Si–Cl

    90

    P≡P

    117

    H–B

    90

    Si–O

    110

    C≡O

    258

    H–S

    81

    P–Cl

    79

    C≡C

    200

    H–Si

    75

    P–Br

    65

    N≡N

    226

    H–P

    77

    P–O

    90

    C≡N

    213

    Bond Dissociation Energies

    atom or
    group

    methyl

    ethyl

    i-propyl

    t-butyl

    phenyl

    benzyl

    allyl

    acetyl

    vinyl

    H

    103

    98

    95

    93

    110

    85

    88

    87

    112

    F

    110

    110

    109

     

    124

    94

     

    119

     

    Cl

    85

    82

    81

    80

    95

    68

    70

    82

    90

    Br

    71

    70

    69

    66

    79

    55

    56

    68

    80

    I

    57

    54

    54

    51

    64

    40

    42

    51

     

    OH

    93

    94

    92

    91

    111

    79

    82

    107

     

    NH2

    87

    87

    86

    85

    104

    72

    75

    95

     

    CN

    116

    114

    112

     

    128

    100

       

    128

    CH3

    88

    85

    84

    81

    101

    73

    75

    81

    98

    C2H5

    85

    82

    81

    78

    99

    71

    72

    78

    95

    (CH3)2CH

    84

    81

    79

    74

    97

    70

    71

    76

    93

    (CH3)3C

    81

    78

    74

    68

    94

    67

    67

     

    89

    C6H5

    101

    99

    97

    94

    110

    83

    87

    93

    108

    C6H5CH2

    73

    71

    70

    67

    83

    59

    59

    63

    81

    Many of the bond energies listed here were taken from the following sources:

    • R.T.Sanderson, Polar Covalence, 1983
    • R.T.Sanderson, Chemical Bonds and Bond Energy, 1976

    William Reusch, Professor Emeritus (Michigan State U.), Virtual Textbook of Organic Chemistry