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T3: Bond Energies

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