T3: Bond Energies
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The following tables list experimental bond dissociation enthalpies of common bonds at 298 K.
R-H bonds
Bond | ΔH298(kcal.mol-1) | ΔH298 (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 |
Bond | ΔH298(kcal.mol-1) | ΔH298 (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 |
- | - | - |
Bond | ΔH298(kcal.mol-1) | ΔH298 (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 |
Bond | ΔH298(kcal.mol-1) | ΔH298 (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 |
Bond | ΔH298(kcal.mol-1) | ΔH298 (kJ.mol-1) |
---|---|---|
HOO-H | 87.8 | 367.4 |
CH3OO-H | 88 | 368 |
CH3CH2OO-H | 85 | 356 |
(CH3)3COO-H | 84 | 351 |
Bond | ΔH298(kcal.mol-1) | ΔH298 (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 |
Bond | ΔH298(kcal.mol-1) | ΔH298 (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 |
CH3CH2O-CH3 | 81 | 339 |
- Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255.
- Feng, Y.; Huang, H.; Liu, L.; Guo, Q.-X. Phys. Chem. Chem. Phys. 2003, 5, 685.
- Zavitsas, A. A. J. Phys. Chem. A 2003, 107, 897.
- McGivern, S. W.; Derecskei-Kovacs, A.; North, S. W.; Francisco, J. S. J. Phys Chem. A 2000, 104, 436.
- Jursic, B. S. J. Chem. Soc. Perkin Trans. 1999, 2, 369.
- Verevkin, S. P.; Krashnykh, E. L.; Wright, J. S. Phys. Chem. Chem. Phys. 2003, 5, 2605.
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 |
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 |
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 |
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
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