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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

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

     

    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.

     

    Enthalpy Change, Single Bonds (first half)
    Single Bonds ΔH°*
    H–H 104.2
    C–C 83
    N–N 38.4
    O–O 35
    F–F 36.6
    Si–Si 52
    P–P 50
    S–S 54
    Cl–Cl 58
    Br–Br 46
    I–I 36.
    H–C 99
    H–N 93
    H–O 111
    H–F 135
    H–Cl 103
    H–Br 87.5
    H–I 71
    H–B 90
    H–S 81
    H–Si 75
    H–P 77
    Enthalpy Change, Single Bonds (second half)
    Single Bonds ΔH°*
    B–F 150
    B–O 125
    C–N 73
    N–CO 86
    C–O 85.5
    O–CO 110
    C–S 65
    C–F 116
    C–Cl 81
    C–Br 68
    C–I 51
    C–B 90
    C–Si 76
    C–P 70
    N–O 55
    S–O 87
    Si–F 135
    Si–Cl 90
    Si–O 110
    P–Cl 79
    P–Br 65
    P–O 90
    Enthalpy Change, Multiple Bonds
    Multiple Bonds ΔH°*
    C=C 146
    N=N 109
    O=O 119
    C=N 147
    C=O (CO2) 192
    C=O (aldehyde) 177
    C=O (ketone) 178
    C=O (ester) 179
    C=O (amide) 179
    C=O (halide) 177
    C=S (CS2) 138
    N=O (HONO) 143
    P=O (POCl3) 110
    P=S (PSCl3) 70
    S=O (SO2) 128
    S=O (DMSO) 93
    P=P 84
    P≡P 117
    C≡O 258
    C≡C 200
    N≡N 226
    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