8 - Bond Dissociation Enthalpy Data

The Lectka Group at Johns Hopkins
University
Bond Dissociation Enthalpy Data
http://www.jhu.edu/chem/lectka/Extras.html
Compound
NC
Bond Dissociation Enthalpy (kcal/mol)

Theory Level
Bond (C-Y)
Energy
C-CN
CH3
CH3
NC
121.6
Me
Me
120.9
NC
Me
122.4
Me
Me
117.8
NC
NC
133
NC
108.7
CN
134
Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255
C-CN
H2N
111.4
CN
O
HO
CN
110.6
O
H 3C
CN
O
H
CN
110.5
110.1
O
F
CN
O
HOOC
CN
110.0
109.7
O
F3C
CN
O
NC
109.6
109.4
CN
O
O2N
CN
Feng, Y.; Huang, H.; Liu, L.; Guo, Q.-X.Phys. Chem. Chem. Phys. 2003, 5 , 685-690
109.1
Compound

Theory Level
Bond (C-Y)
Energy
C-CN
O
H
CN
104.7
G3
107.3
G3
108.9
G3
110.1
CBS-4M
83.5
G3
83.4
84.4
G3
Experimental
84.1
G3
86.4
CBS-4M
O
Me
CN
O
CN
O
CN
O
CH3
H
O
CH3
Me
O
CH3
O
CH3
Polycyclic Aromatic Hydrocarbon Borders

Zigzag border
Armchair border
Second Armchair dissociation
C-CH3
~428
~394
~287
May, K.; Dapprich, S.; Furche, F.; Unterreiner, B. V.; Ahlrichs, R.Phys. Chem. Chem. Phys. 2000, 2 , 5084-5088
Me
H3C
Me
Me
F
C-C
91.3
91.5
92.3
G2
G2MP2
G2MS
90.3
90.6
91.2
G2
G2MP2
G2MS
97.0
97.2
G2MP2
G2MS
94.4
94.7
G2MP2
G2MS
97.8
98.0
G2MP2
G2MS
CF3
F3C
F
F
F
F
CF3
F 3C
F
CF3
F 3C
F
Fukaya, H.; Ono, T.; Abe, T.J. Phys. Chem. A 2001, 105 , 7401-7404
Compound
CCl3
CH3

Theory Level
Bond (C-Y)
Energy
C-C
89.36
87.0
87.88
89.41
ab-inito
Experimental
0K
Equilibrium Distance D e
CFCl2
CH3
93.85
92.36
93.68
ab-inito
0K
CF 2Cl
CH3
97.30
95.82
97.09
ab-inito
0K
100.91
101
99.42
100.58
ab-inito
Experimental
0K
CF3
CH 3
CF3
CClH2
96.34
94.86
90.07
ab-inito
0K
CF3
CCl2H
91.85
90.37
91.60
ab-inito
0K
CF3
CCl3
86.87
85.39
86.67
ab-inito
0K
CF3
CCl2F
90.57
89.28
90.61
ab-inito
0K
CF 3
CClF2
93.55
92.15
93.53
ab-inito
0K
CF3
CF3
Olleta, A. C.; Lane, S. I.Phys. Chem. Chem. Phys. 2001, 3 , 811-818
96.20
98.7, 97.27
94.27
96.73
ab-inito
Experimental
0K
Compound

Theory Level
Bond (C-Y)
Energy
95.2
88.0
86.6
DFT-AM1
Experimental
Corrected
CF 3
102.3
101.2
93.1
DFT-AM1
Experimental
Corrected
CF3
CF3
93.3
96.9
84.9
DFT-AM1
Experimental
Corrected
CF3
CN
128.5
123.9
116.9
DFT-AM1
Experimental
Corrected
CN
CN
146.7
128.0
133.5
DFT-AM1
Experimental
Corrected
73.8
69.0
67.2
DFT-AM1
Experimental
Corrected
83.6
72.7
76.0
DFT-AM1
Experimental
Corrected
68.8
65.7
62.6
DFT-AM1
Experimental
Corrected
79.1
67.4
72.0
DFT-AM1
Experimental
Corrected
76.5
68.1
69.6
DFT-AM1
Experimental
Corrected
72.2
65.4
65.7
DFT-AM1
Experimental
Corrected
86.5
73.8
78.7
DFT-AM1
Experimental
Corrected
CH3
CH3
CH3
Me
CN
H3C
NH2
O
Me
O
Me
C-C
O
OH
O
CF3
Jursic, B. S. J. Chem. Soc. Perkin Trans. 1999, 2 , 369-372
Compound

Theory Level
Bond (C-Y)
Energy
376.5
371.4
ab-initio
Experimental
378.2
370.4
ab-initio
Experimental
376.3
367.5
ab-initio
Experimental
CH3
371.5
371.2
ab-initio
Experimental
Cl
375.8
365.4
ab-initio
Experimental
378.0
365.1
ab-initio
Experimental
Cl
375.4
375.4
ab-initio
Experimental
CH3
370.7
375.9
ab-initio
Experimental
Cl
C-C
H3 C
Cl
H3 C
Cl
H3 C
Me
H3 C
Cl
Cl
CH3
Cl
H3C
H 3C
Seetula, J. A. J. Chem. Soc Faraday Trans. 1998, 94 , 891-898
C-C
91
H
H
78.7
C O
H
H
H
H
H
H
H
H
H 2C
H 3C
CH3
142.4
178.2
230.7
165
99.4
174.1
90.1
Compound

Theory Level
Bond (C-Y)
Energy
C-Ph
103.5
CH3
CH 3
102.2
Me
101.0
Me
Me
98.3
Me
Me
116
118
97
101
OMe
99.3
H
O
98.8
Me
CH3
77.6
Me
76.7
Me
76.4
Me
65.2
O
71.4
Me
C-C
Me
H3C
Me
Me
89.0
87.9
Me
125.1
Me
77
Compound

Theory Level
Bond (C-Y)
Energy
C-CHCH2
H3C
101.4
Me
100.0
Me
Me
99.2
Me
Me
Me
97.8
116
87.3
116
41
Me

H3C
C-CH2CHCH2
76.5
Me
75.4
Me
75.2
Me
Me
Me
Me
73.2
87.3
62.7

H
C-CCH
CH3
126.5
125.1
Me
Me
124.5
Me
Me
Me
Me
122.3
78
Me
H
Me
77
Compound
Me

Theory Level
Bond (C-Y)
Energy
Me
Me
C-C(CH3)3
87.5
H3 C
Me Me
Me
85.6
Me
Me
Me
Me
Me Me
Me Me
Me
Me
Me Me
Me Me
Me
82.7
Me
Me
Me
73.2
78.6
97.8
Me
Me
Me
Me
98.3
Me
Me
84
MeO
O
Me
Me
Me
79.4
Me

H3C
C-CH3
CH3
Me
H3 C
Me
H3C
Me
90.1
89.0
Me
88.6
Me
Me
87.5
H3C
H3C
101.4
76.5
H3C
CH3
103.5
CH3
77.6
H3C
OMe
83.2
O
H
CH3
84.8
O
Me
CH3
84.5
Compound

Theory Level
Bond (C-Y)
Energy
C-CH3
85.5
O
H2N
CH3
O
86.1
HO
CH3
O
H3C
86.2
CH3
O
86.4
H
CH3
86.5
F
CH3
O
87.1
HOOC
CH3
O
F 3C
87.2
CH3
O
87.4
NC
CH3
87.6
O2N
CH3
C-CH2CH3
Me
H3C
89.0
Me
87.9
Me
Me
Me
87.1
Me
Me Me
Me
Me
85.6
Me
100.0
Me
75.4
Me
102.2
Me
76.7
Me
85
MeO
O
H
Me
Me
O
Me
83.3
83.5
Compound

Theory Level
Bond (C-Y)
Energy
Me
C-CH(CH3)2
Me
88.6
H3 C
Me
87.1
Me
Me
Me
85.6
Me
Me
Me
Me
Me
Me
Me
82.7
Me
Me
Me
99.2
Me
75.2
Me
Me
101.0
Me
Me
Me
76.4
Me
85.8
Me
MeO
O
Me
83.1
Me
O
Me
Me
81.9
Me
C-C
Me
87.8
Experimental
85.1
82.8
Experimental
B3LYP/6-31G(d), 298K
87.3
80.6
Experimental
B3LYP/6-31G(d), 298K
van Scheppingen, W.; Dorrestijn, E.; Arends, I.; Mulder, P.J. Phys. Chem. A 1997, 101, 5404-5411
Compound
H3C
CH3

Theory Level
Bond (C-Y)
Energy
C-C
89.68
172.2
229.9
Ph
Ph
Ph
Ph
Me
t-Bu
Me
Me
Ph
16.6
Ph
t-Bu
44.0
Me
43.7
Me Me
Me Me
Et
Ph
Et
Et
Et
Et
Et
i-Bu
Et
Et
i-Pr
Et
Et
Me
Et
Et
Ph
44.7
Et
Et
Et
51.0
Et
Et
i-Bu
57.8
Et
Et
i-Pr
62.2
Et
Et
Me
60.2
Et
Ph
66.6
Ph
Cl
Cl
Cl
Cl
Cl
Cl
70.1
Me
Me
Me
Me
76.0
Me
Me
Me
Me
Me
Me
H3C
Cl
Cl
86.6
88.3
Cl
Zavitsas, A. A. J. Phys. Chem. A 2003, 107, 897-898
Reference includes bond distances in Angstroms
Compound
H 3C
Me
Me
Me
Me
H 3C

Theory Level
Bond (C-Y)
Energy
C-C
86.0
88.9
Me
Me
87.2
Me
Me
Me
Me
Ph
Me
Me
Me
H
H
97.4
97.5
H
Me
Ph
102.1
Me
Me
102.3
Ph
H
Me
99.7
Me
H
H
CH3
H
100.9
H
CH3
103.9
Me
99.6
H
H
111.9
118.0
116.9
Me
Me
Me
115.8
Compound

Theory Level
Bond (C-Y)
Energy
C-C
CH3
121.1
H
H
116.0
H
H
123.5
CH3
132.7
N
H
132.1
N
H
H
140.7
H
H
H
133.6
H
H
155.0
152.4
C-C
Me
CH3
Me
Lie, W.; Fedorov, D. G.; Hirao, K.J. Phys. Chem. A 2002, 106, 7057-7061
66.10
66.06
86.06
86.04
81.77
81.76
HF and NR
HF and RESC
B3LYP and NR
B3LYP and RESC
BOP and NR
BOP and RESC
Compound
H3 C
CH 3
CH3
Me
CH 3
Me
CH3
Me
Me
Me
Me
CH3
Me
CH3

Theory Level
Bond (C-Y)
Energy
C-C
84.3
85.9
86.4
88.6
88.1
87.4
90.4
B3LYP
B3PW91
MPW1PW91
B3P86
CCSD(T)
G2MSr
Experimental
81.4
83.0
83.8
85.7
87.4
87.0
85.8
B3LYP
B3PW91
MPW1PW91
B3P86
CCSD(T)
G2MSr
Experimental
96.5
97.9
98.8
100.8
101.8
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
78.7
80.3
81.3
83.2
86.5
86.6
85.7
B3LYP
B3PW91
MPW1PW91
B3P86
CCSD(T)
G2MSr
Experimental
76.0
77.6
78.8
80.7
85.4
86.0
84.1
B3LYP
B3PW91
MPW1PW91
B3P86
CCSD(T)
G2MSr
Experimental
66.4
68.5
69.7
71.2
78.1
74.6
B3LYP
B3PW91
MPW1PW91
B3P86
G2MSr
Experimental
Yao, X.-Q.; Hou, X.-J.; Wu, G.-S.; Xu, Y.-Y.; Xiang, H.-W.; Jiao, H.; Li, Y.-W.J. Phys. Chem. A 2002, 106, 7184-7189
Compound

Theory Level
Bond (C-Y)
Energy
C-C
Me
Me
CH3
Me
CH3
Me
Me
Me
CH3
Me
66.3
68.6
69.8
71.2
71.8
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
66.9
69.2
70.5
71.9
72.1
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
69.1
71.4
72.3
73.9
75.8
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
60.2
62.9
64.3
65.4
67.6
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
66.3, 63.0
68.9, 65.5
70.3, 67.2
71.8, 68.9
B3LYP
B3PW91
MPW1PW91
B3P86
92.4
93.9
95.1
96.9
B3LYP
B3PW91
MPW1PW91
B3P86
108.0
109.5
110.8
112.9
113.7
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
79.6
82.0
83.4
84.8
89.6
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
Compound

Theory Level
Bond (C-Y)
Energy
C-C
Me
Me
Me
Me
Me
Me
93.1
94.6
95.8
97.6
B3LYP
B3PW91
MPW1PW91
B3P86
92.6
94.2
95.4
97.2
B3LYP
B3PW91
MPW1PW91
B3P86
87.4
89.4
91.1
92.9
B3LYP
B3PW91
MPW1PW91
B3P86
76.2
78.6
80.9
82.9
B3LYP
B3PW91
MPW1PW91
B3P86
91.0
92.7
94.1
95.9
B3LYP
B3PW91
MPW1PW91
B3P86
74.8
77.1
79.0
80.3
B3LYP
B3PW91
MPW1PW91
B3P86
73.3
76.0
78.2
79.5
B3LYP
B3PW91
MPW1PW91
B3P86
Compound

Theory Level
Bond (C-Y)
Energy
C-C
Me
Me
Me
Me
Me
Me
Me
54.1
57.1
58.5
59.5
61.4
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
46.9
49.9
52.1
52.9
B3LYP
B3PW91
MPW1PW91
B3P86
32.7
36.9
39.7
39.8
47.5
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
75.7
78.0
79.7
79.7
B3LYP
B3PW91
MPW1PW91
B3P86
66.8
69.0
70.3
71.6
73.9
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
31.8
35.4
38.5
39.5
B3LYP
B3PW91
MPW1PW91
B3P86
43.4
46.7
48.8
49.3
57.8
B3LYP
B3PW91
MPW1PW91
B3P86
Experimental
Compound
Heterolysis
G (kcal/mol)
Bond (C-Y)
Energy
(Solvent)
C-C
R=
8.7
(DMSO)
8.2
(DMSO)
8.3
19.6
(DMSO)
+
R =
8.2
9.3
(DMSO)
(Sulfolane)
R+ =
8.2
9.2
(DMSO)
(Sulfolane)
R+ =
7.7
8.0
(DMSO)
(Sulfolane)
R+ =
7.1
8.0
(DMSO)
(Sulfolane)
R+ =
4.9
6.8
(DMSO)
(Sulfolane)
R+ =
5.2
6.5
(DMSO)
(Sulfolane)
R+ =
5.4
6.5
(DMSO)
(Sulfolane)
5.9
(DMSO)
5.5
11.9
(DMSO)
Br
R+ =
R+ =
Hohet
R=
Cl
R=
o
H het
Kitagawa, T.; Takeuchi, K.J. Phys. Org. Chem. 1998, 11 , 157-170
Compound
Heterolysis
o
G (kcal/mol)
Bond (C-Y)
Energy
(Solvent)
C-C
R=
4.6
(DMSO)
4.8
(DMSO)
Me
C
Me
R=
Me
R=
Me
4.6
(DMSO)
R=
OMe
4.6
(DMSO)
<4
4.8
(DMSO)
(CH3CN)
5.7
(ClCH2CH2Cl)
6.7
6.6
(CH2Cl2)
(THF)
R =
<4
(DMSO)
R+ =
<4
(DMSO)
R+ =
<4
(DMSO)
R=
R=
<4
(DMSO)
Compound
Heterolysis
o
G (kcal/mol)
Bond (C-Y)
Energy
C-C
(Solvent)
Go
R =
9.3
(DMSO, CS2)
R+ =
8.2
(DMSO, CS2)
R+ =
7.7
(DMSO, CS2)
6.2
(DMSO, CS2)
<4
(DMSO, CS2)
<4
(DMSO, CS2)
R=
R+ =
R+ =
Me
Compound
R4
R1
R1 = CPh3, R2 = COOMe
R3, R4 = H

Theory Level
Bond (C-Y)
Energy
C-R1 heterol.
25.81
homolysis
16.08
R1 = CPh3, R2 = SO 2Ph
R3, R4 = H
heterolysis
homolysis
28.35
22.38
R1 = CPh3, R2 = SPh
R3 = H, R4 = Br
heterolysis
homolysis
29.41
15.60
R1 = CPh3, R2 = SPh
R3, R4 = H
heterolysis
homolysis
33.61
12.96
R1 = CPh3, R2 = Ph
R3, R4 = H
heterolysis
homolysis
35.51
13.18
R1 = Xan, R2 = COOMe
R3, R4 = Br
heterolysis
homolysis
24.62
26.03
R1 = Xan, R2 = COOMe
R3, R4 = H
heterolysis
homolysis
27.33
22.53
R1 = Xan, R2 = SPh
R3 = H, R4 = Br
heterolysis
homolysis
30.13
21.25
R1 = Xan, R2 = SPh
R3, R4 = H
heterolysis
homolysis
33.03
20.69
R1 = TPCP, R2 = COOMe
R3, R4 = Br
heterolysis
homolysis
16.22
39.70
R1 = TPCP, R2 = CN
R3, R4 = H
heterolysis
homolysis
19.56
38.54
R1 = TPCP, R2 = COOMe
R3, R4 = H
heterolysis
homolysis
20.62
37.89
R1 = TPCP, R2 = SO 2Ph
R3, R4 = H
heterolysis
homolysis
22.23
43.26
R1 = TPCP, R2 = SPh
R3 = H, R4 = Br
heterolysis
homolysis
25.40
38.59
R1 = TPCP, R2 = SPh
R3, R4 = H
heterolysis
homolysis
27.49
37.22
R1 = TPCP, R2 = Ph
R3, R4 = H
heterolysis
homolysis
29.34
34.02
R2
R3
Arnett, E.M.; Venimadhavan, S.J . Am. Chem. Soc. 1991, 113 , 6967-6975
Compound
R4
R1

Theory Level
Bond (C-Y)
Energy
R1 = C7H7, R2 = CO2Me
R3, R4 = Br
C-R1 heterol.
homolysis
19.45
27.20
R1 = C7H7, R2 = CO2Me
R3, R4 = H
heterolysis
homolysis
24.89
26.44
R1 = C7H7, R2 = SO 2Ph
R3, R4 = H
heterolysis
homolysis
27.17
32.47
R1 = C7H7, R2 = SPh
R3 = H, R4 = Br
heterolysis
homolysis
28.59
26.05
R1 = C7H7, R2 = SPh
R3, R4 = H
heterolysis
homolysis
30.52
24.52
R1 = C7H7, R2 = Ph
R3, R4 = H
heterolysis
homolysis
33.84
22.79
R1 = CPh3, R2 = COOMe
R3, R4 = Br
heterolysis
homolysis
19.76
16.23
R2
R3
Arnett, E.M.; Venimadhavan, S.J . Am. Chem. Soc. 1991, 113 , 6967-6975
C5 H11
C5 H11
C-C
Leal, J. P.; Marques, N.; Takats, J.J. Organomet. Chem. 2001, 632 , 209214
(kJ/mol)
361.7
Compound

Theory Level
Bond (C-Y)
Energy
R=H
R = Me3C
R = Ph3C
R = Me3Si
R = Et3Si
R = Ph3Si
R = PhSO2CH4
R = PhSO2CH2SiMe3
R = PhSO2CH2SiPh3
R = PhSO2CH(SiMe3)2
R = PhS(O)(=NSO2Tol)CH3
R = PhS(O)(=NSO2Tol)CH(SiMe3)2
R = PhSO2CH2Ph
R = PhSO2CH(CH=CH2)(SiMe3)
H R
C-H
79.5
79.4
77.2
82.5
81.2
80.6
99
99.4
97.4
96.5
103.1
99.8
90.2
91.1
Zhang, S.; Zhang, X-M.; Bordwell, F. G.J. Am. Chem. Soc. 1995, 117, 602-606.
R = PhCH2
C-H heterol.
homolysis
64.2
67.9
R = 4-CH3OPh
heterolysis
homolysis
66.9
69.4
R = 4-CH3Ph
heterolysis
homolysis
67.5
69.2
R = Ph
heterolysis
homolysis
68.8
69.2
R = 4-ClPh
heterolysis
homolysis
70.2
69.1
R = 4-BrPh
heterolysis
homolysis
70.4
69.2
R = 4-CF3Ph
heterolysis
homolysis
72.6
69.5
CO2Et
R=H
CH3
R = CH3
C-H heterol.
homolysis
heterolysis
homolysis
69.3
69.4
69.9
68.8
C-H heterol.
homolysis
81.1
73.7
H H
CONH2
N
R
EtO2C
H3C
N
R
H
R = CH3
N
R
Chem. Eur. J. 2003, 9(4) , 871-880
Compound
H3 C

Theory Level
Bond (C-Y)
Energy
C-H
C-O
H3C OO
105.5
105.5
105.5
105.8
104.9
105.3
104.9
B3LYP-LLM
B3LYP-MLM1
B3LYP-MLM2
B3LYP-HLM
G3
G3MP2
Experimental
89.3
89.4
90.1
90.6
91.1
93.1
88.5
B3LYP-LLM
B3LYP-MLM1
B3LYP-MLM2
B3LYP-HLM
G3
G3MP2
Experimental
86.9
87.1
87.9
88.1
87.5
88.6
88.2
B3LYP-LLM
B3LYP-MLM1
B3LYP-MLM2
B3LYP-HLM
G3
G3MP2
Experimental
71.9
72.6
74.1
74.2
75.6
77.3
76.4
B3LYP-LLM
B3LYP-MLM1
B3LYP-MLM2
B3LYP-HLM
G3
G3MP2
Experimental
80.7
80.8
82.0
82.3
82.1
83.7
83.5
B3LYP-LLM
B3LYP-MLM1
B3LYP-MLM2
B3LYP-HLM
G3
G3MP2
Experimental
32.7
35.9
34.1
32.4
32.2
32.7
B3P86-LLM
B3P86-MLM
B3P86-MLM
G3MP2
G3
Experimental
Pratt, D. A.; Mills, J. H.; Porter, N. A. J. Am. Chem. Soc. 2003, 125 , 5801-581 Reference includes radical stabilization energies
Compound

Theory Level
Bond (C-Y)
Energy
C-R
Me
trans, cis
19.6, 23.1
83.4, 87.0
B3P86-HLM
B3LYP-HLM
R = OO
20.5, 21.3
84.0, 84.9
B3P86-HLM
B3LYP-HLM
R = OO
7.9, 7.4
73.1, 72.7
B3P86-HLM
B3LYP-HLM
R = OO
8.4,
73.5,
B3P86-HLM
B3LYP-HLM
R = OO
14.2, 77.4
15.3, 78.5
B3P86-HLM
B3LYP-HLM
R = OO
14.6, 77.7
15.7, 78.8
B3P86-HLM
B3LYP-HLM
R=H
R = OO
4.2
69.8
B3P86-HLM
B3LYP-HLM
R = OO
R=H
6.0
71.5
B3P86-HLM
B3LYP-HLM
R=H
R = OO
9.8, 11.2
72.9, 74.3
B3P86-HLM
B3LYP-HLM
R = OO
R=H
11.7, 12.9
75.1, 76.3
B3P86-HLM
B3LYP-HLM
Me
R = OO
R=H
Me
R=H
dissociated radical
as trans or cis
Me
Me
Me
R=H
R
Me
Me
R=H
R
Me
Me
Me
R=H
R=H
Me
Me
Me
R
R
Me
Me
Me
Me
R
R
Me
Me
Pratt, D. A.; Mills, J. H.; Porter, N. A. J. Am. Chem. Soc. 2003, 125 , 5801-5810
Compound

Theory Level
Bond (C-Y)
Energy
O
H
CF3
O
O
C2F5
O
O
C3F7
O
O
C4F9
O
O
O
H
O
O
CHF2
F
O
O
CHF2
F
O
H
CHF2
O
O
CF3
H
O
O
CF3
F
CHF2
O
F
O
H
F
O
O
H
F
O
O
H
H
O
H
O
CHF2
F F
F
CF 3
H F
F
CF 3
H F
F
CF3
F F
F
CF3
F
100.4
96.5
Syn
Anti
100.2
96.7
Syn
Anti
100.2
96.7
Syn
Anti
100.1
96.8
Syn
Anti
104.3
105.0
Syn
Anti
100.2
96.0
Syn
Anti
102.2
101.9
Syn
Anti
99.8
96.6
Syn
Anti
102.2
99.7
Syn
Anti
100.8
95.3
Syn
Anti
101.6
101.0
Syn
Anti
100.1
96.6
Syn
Anti
100.8
100.9
Syn
Anti
99.6
96.6
Syn
Anti
101.8
99.3
Syn
Anti
100.8
95.4
O
O
C-H Syn
Anti
Urata, S.; Uchimaru, T.; Chandra, A. K.; Takada, A.; Sekiya, A.J. Chem. Kinetics 2002, 34 , 524-530
All Calculated with DFT

(RO)B3LYP/6-311G
Compound
CH3OCH3
CF3OCH3
CF3OCHF2
CHF2 OCHF2
CF3CF2OCH3
CF3 CF2CF 2OCH3
(CF3)2CFOCH3
CF3 CH3
CF3CH2F
CF3CHF2
CF3 CH2Cl
CF3 CHCl2
CF3 CHFCl
CF2 ClCH3
CF2 ClCH2F
CF2 ClCHF2
CF2ClCH 2Cl
CF2 ClCHCl2
CF2 ClCHFCl
CFCl2 CH 3
CFCl2CH2F
CFCl2CHF2
CFCl2CH 2Cl
CFCl2 CHCl2
CFCl2 CHFCl
CCl3CH 3
CCl3CH2F
CCl3CHF 2
CCl3CH2Cl
CCl3CHCl2
CCl3CHFCl
CHF2 CHF2
CF3CHFCF3
CF3CH2CHF2
CF3 CH2CHF2
CF3CH2CH2CF3
CF3CH2CF2CH3
CF3CH2CF2CH3
CHF2 CF2CF2CHF2
CF3CF2CH2CH2CF2 CF3
CH 3OCH2F
CH 3OCH2F
CH 3OCHF2
CH 3OCHF2
CF3OCH3
CF3OCHF2
CH 2FOCH2 F
CHF 2OCHF 2
CF3CF2OCH3

Theory Level
Bond (C-Y)
Energy
C-H
95.7
100.7
103.5
103.4
100.9
101.1
99.8
106.0
101.1
102.0
99.5
95.3
98.9
104.0
99.6
100.7
98.6
93.7
97.5
102.9
98.9
100.9
97.5
93.7
97.3
102.6
98.6
101.0
97.2
94.1
97.5
102.8
101.0
101.3
104.8
102.3
102.6
104.5
102.0
103.2
97.4
97.9
102.8
100.0
100.7
103.5
99.7
103.4
100.9
Chandra, A. K.; Uchimaru, T.; Urata, S.; Sugie, M.; Sekiya, A.J. Chem. Kinetics 2003, 35(3) , 130-138
Compound
CF3CF2CF2 OCH3
(CF3)2CFOCH3
CH3OCF2CHF2
CH3OCF2CHF2
CH2 FCF2OCHF2
CH2 FCF2OCHF2
CHF2CF2OCH 2CF3
CHF2CF2OCH 2CF3
CF3CHFCF2OCH3
CF3CHFCF2OCH3
CF3CH 2OCH2 CF3
CF3CF 2CH2OCHF2
CF3CF 2CH2OCHF2
CHFClCF2 OCH 3
CHFClCF2 OCH 3
CHF2OCF2CHFCl
CHF2OCF2CHFCl
CHF2OCHClCF3
CHF2OCHClCF3

Theory Level
Bond (C-Y)
Energy
C-H
101.1
99.8
101.8
100.5
103.9
101.5
99.5
102.3
100.7
100.6
96.9
103.9
98.4
98.8
100.6
99.1
103.8
98.3
103.7
Napthalene
C-H
Napthalene
111.2
110.7
111.9
110.6
Reed, D. R.; Kass, S. R. J. Mass Spectrom . 2000, 35 , 534539

CF3
CH3
F3 C
CH2F
F3 C
CHF2
F3 C
CH2Cl
F3C
CHCl2
F3 C
CHFCl
CF2Cl
CHCl2
CF2 Cl
CHFCl
CFCl2
CCl3
CHFCl
CH 3
CH3OCH3
CF3OCH3
C-H
106.0
101.1
102.0
99.5
95.3
98.9
93.7
97.5
97.3
102.6
95.7
100.7
B3LYP/6-31+G(d)
B3LYP/6-31+G(d)
Compound

Theory Level
Bond (C-Y)
Energy
C-H homolytic
NO2
87
Me
H
H
86.5
O2N
NO2
85
NO2
87
H
O2N
H3CO
NO2
H
Me
NO2
H
Me
85
87
H3 CO
NO2
H
Me
85.5
Me
NO2
H
Me
86
NO2
H
Me
86
NO2
H
Me
87
O2N
O 2N
NO2
H
Me
87
O2N
NO2
H
Me
89
O2N
J . Org. Chem . 1995, 60 , 6348-6352
Reference includes radical anion dissociation energies
Compound

Theory Level
Bond (C-Y)
Energy
o
C-H (O K)
35.6
CBS-4
o
298 K
36.3
CBS-4
Experimental
35.2
OoK
35.6
CBS-4
o
298 K
36.4
CBS-4
Experimental
35.0
H
H 2C
H
Me
H
Me
Me
Me
Me
Me
Me
H
CH2
Me
CH 2
Me
H
Me
Me
CH2
Me
Me
Me
Me
Zhang, X.-M.J. Org. Chem. 1998, 63, 1872-1877
OoK
298oK
Experimental
35.6
36.3
34.9
CBS-4
CBS-4
OoK
298oK
Experimental
35.4
36.2
34.9
CBS-4
CBS-4
OoK
298oK
Experimental
35.4
36.2
33.3
CBS-4
CBS-4
OoK
298oK
Experimental
32.3
33.2
31.9
CBS-4
CBS-4
OoK
298oK
Experimental
32.6
33.4
32.0
CBS-4
CBS-4
OoK
298oK
Experimental
29.8
30.8
29.7
CBS-4
CBS-4
cis
trans
o
298 K cis
trans
Experimental cis
trans
34.1
32.5
35.0
33.5
33.2
32.2
CBS-4
CBS-4
CBS-4
CBS-4
OoK
298oK
Experimental
33.9
35.0
34.0
CBS-4
CBS-4
OoK
298oK
Experimental
33.1
34.2
32.5
CBS-4
CBS-4
OoK
298oK
Experimental
48.1
49.2
47.6
CBS-4
CBS-4
OoK
Compound
Me

Theory Level
Bond (C-Y)
Energy
o
C-H (O K)
47.7
CBS-4
298oK
48.5
CBS-4
Experimental
47.5
OoK
298oK
Experimental
OoK
298oK
Experimental
45.2
46.4
44.2
47.5
48.5
44.6
CBS-4
CBS-4
cis
trans
o
298 K cis
trans
Experimental cis
trans
45.7
44.8
46.9
46.0
45.5
44.3
CBS-4
CBS-4
CBS-4
CBS-4
OoK
298oK
Experimental
44.6
45.6
45.8
CBS-4
CBS-4
OoK
298oK
Experimental
49.4
50.6
49.3
CBS-4
CBS-4
OoK
298oK
Experimental
44.6
45.5
47.5
CBS-4
CBS-4
OoK
298oK
44.3
45.2
CBS-4
CBS-4
OoK
298oK
Experimental
29.7
30.5
32.5
CBS-4
CBS-4
OoK
298oK
Experimental
109.0
110.6
110
CBS-4
CBS-4
OoK
298oK
Experimental
37.9
39.1
35.6
CBS-4
CBS-4
Me
OoK
298oK
105.8
107.4
CBS-4
CBS-4
OoK
298oK
Experimental
35.0
36.1
36.2
CBS-4
CBS-4
Me
H
Me
OoK
H
Me
CBS-4
CBS-4
Me
H
CH2
H
Me
H
Zhang, X.-M.J. Org. Chem. 1998, 63 , 1872-1877
Compound

Theory Level
Bond (C-Y)
Energy
Me
H
H
H
Me
Me
H
Me
CH 2
H
Me
o
C-H (O K)
o
298 K
OoK
298oK
Experimental
OoK
298oK
110.0
111.5
30.7
31.9
32.1
109.6
111.1
OoK
298oK
Experimental
31.1
32.3
32.5
CBS-4
CBS-4
OoK
298oK
Experimental
OoK
298oK
Experimental
57.2
58.6
58.9
54.0
55.0
60.0
CBS-4
CBS-4
OoK
298oK
53.5
54.7
CBS-4
CBS-4
C-H
111.4
110.9
110.6
Experimental
B3LYP/6-31G(d), 298K
B3LYP/6-311++G(d,p), 298K
108.9
109.3
108.3
Experimental
B3LYP/6-31G(d), 298K
B3LYP/6-311++G(d,p), 298K
88.5
87.9
Experimental
B3LYP/6-31G(d), 298K
88.1
85.1
84.1
Experimental
B3LYP/6-31G(d), 298K
B3LYP/6-311++G(d,p), 298K
CBS-4
CBS-4
CBS-4
CBS-4
CBS-4
CBS-4
CBS-4
CBS-4
Me
Zhang, X.-M.J. Org. Chem. 1998, 63 , 1872-1877
H
Me
Compound
CH4

Theory Level
Bond (C-Y)
Energy
106.0
118.9
106.2
102.3
105.1
105.5
102.8
104.9
(RO) B3LYP
(RO) B3PW86
(RO) B3PW91
(RO) PW91LYP
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
MP2/cc-pVtz
Experimental
CH3F
100.6
113.3
100.7
95.3
99.7
101.1
99.7
101.3
(RO) B3LYP
(RO) B3PW86
(RO) B3PW91
(RO) PW91LYP
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
MP2/cc-pVtz
Experimental
CH2F2
100.3
113.1
100.4
94.4
99.7
100.7
100.0
103.2
(RO) B3LYP
(RO) B3PW86
(RO) B3PW91
(RO) PW91LYP
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
MP2/cc-pVtz
Experimental
CHF3
104.9
105.4
105.3
105.1
106.7
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
MP2/cc-pVtz
Experimental
CH3Cl
100.6
113.1
100.6
95.7
99.6
99.5
97.7
100.1
(RO) B3LYP
(RO) B3PW86
(RO) B3PW91
(RO) PW91LYP
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
MP2/cc-pVtz
Experimental
CHCl3
93.1
93.9
92.1
93.2
93.8
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
MP2/cc-pVtz
Experimental
Chandra, A. K.; Uchimaru, T. J. Phys. Chem. A 2000, 104, 9244-9249
C-H
Compound
CH2Cl2

Theory Level
Bond (C-Y)
Energy
96.9
109.3
96.8
91.6
96.0
95.4
93.8
96.2
(RO) B3LYP
(RO) B3PW86
(RO) B3PW91
(RO) PW91LYP
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
MP2/cc-pVtz
Experimental
CH2FCl
98.2
99.0
98.4
100.8
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
Experimental
CHF2Cl
100.5
101.1
100.4
100.7
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
Experimental
CHFCl2
96.8
97.5
96.2
98.9
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
Experimental
CH3Br
100.2
101.2
100.9
98.9
101.6
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
MP2/cc-pVtz
Experimental
CH2Br2
96.1
97.0
96.8
96.3
99.7
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
MP2/cc-pVtz
Experimental
CHBr3
91.7
92.6
92.4
93.2
96.0
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
MP2/cc-pVtz
Experimental
CH2FBr
98.1
98.8
98.5
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
C-H
Compound
CHF2Br

Theory Level
Bond (C-Y)
Energy
C-H
98.9
99.5
99.1
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
CHFBr2
94.9
95.6
94.6
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
CH2ClBr
96.1
97.0
96.2
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
CHCl2Br
92.6
93.4
92.2
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
CHBr2Cl
92.2
93.0
92.2
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
CHFClBr
95.8
96.6
95.9
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
HOH
114.2
115.1
118.4
119.0
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
Experimental
106.0
105.8
106.7
(RO)B3LYP 6-311++G(3df,2p)
Experimental
C-H
F 3C
CH3
F 3C
CH2 F
101.1
101.1
(RO)B3LYP 6-311++G(3df,2p)
F 3C
CHF 2
102.0
101.7
102.7
(RO)B3LYP 6-311++G(3df,2p)
Experimental
F 3C
CH 2Cl
99.5
98.3
101.8
(RO)B3LYP 6-311++G(3df,2p)
Experimental
F 3C
CHCl2
95.3
93.6
95.3
(RO)B3LYP 6-311++G(3df,2p)
Experimental
F 3C
CHFCl
98.9
97.8
99.2
(RO)B3LYP 6-311++G(3df,2p)
Experimental
Compound

Theory Level
Bond (C-Y)
Energy
C-H
104.0
103.8 (RO)B3LYP 6-311++G(3df,2p)
CF2Cl
CH 3
CF2Cl
CH2 F
99.6
100.0
(RO)B3LYP 6-311++G(3df,2p)
CF2Cl
CHF2
100.7
100.4
(RO)B3LYP 6-311++G(3df,2p)
CF2Cl
CH 2Cl
98.6
97.6
(RO)B3LYP 6-311++G(3df,2p)
CF2Cl
CHCl2
93.7
92.1
(RO)B3LYP 6-311++G(3df,2p)
CF2Cl
CHFCl
97.5
96.4
(RO)B3LYP 6-311++G(3df,2p)
102.9
102.9
(RO)B3LYP 6-311++G(3df,2p)
CFCl2
CH3
CFCl2
CH2F
98.9
98.9
(RO)B3LYP 6-311++G(3df,2p)
CFCl2
CHF2
100.9
100.6
(RO)B3LYP 6-311++G(3df,2p)
CFCl2
CH2Cl
97.5
96.7
(RO)B3LYP 6-311++G(3df,2p)
CFCl2
CHCl2
93.7
92.2
(RO)B3LYP 6-311++G(3df,2p)
CFCl2
CHFCl
97.3
96.2
(RO)B3LYP 6-311++G(3df,2p)
102.6
102.5
(RO)B3LYP 6-311++G(3df,2p)
CCl3
CH3
CCl3
CH2F
98.6
98.7
(RO)B3LYP 6-311++G(3df,2p)
CCl3
CHF2
101.0
100.7
(RO)B3LYP 6-311++G(3df,2p)
CCl3
CH 2Cl
97.2
96.2
(RO)B3LYP 6-311++G(3df,2p)
CCl3
CHCl2
94.1
92.5
94.9
(RO)B3LYP 6-311++G(3df,2p)
Experimental
CCl3
CHFCl
97.5
96.4
(RO)B3LYP 6-311++G(3df,2p)
Compound
CH3

Theory Level
Bond (C-Y)
Energy
C-H
CH2F
102.8
103.8
105.1
corrected MP2/cc-pVtz
CCSD(T)/6-311++G(3df,3pd)
Experimental
99.7
98.5
101.3
Experimental
CH2Cl
97.7
96.6
99.5
Experimental
CH2Br
98.9
97.6
101.6
Experimental
100.0
101.3
Experimental
CHF2
CHCl2
93.8
95.6
Experimental
CHBr2
96.3
99.7
Experimental
105.1
106.7
Experimental
CF3
CCl3
93.2
95.8
Experimental
CBr3
93.2
96
Experimental
McGivern, W. S.; D.-K., A.; North, S. W.; Francisco, J. S. J. Phys. Chem. A 2000, 104, 436-442
Tp'Rh(CNneo)(R)H R = Ph
C-H
113.5
Bu
R=
109.7
R = Me
R = n -pentyl
Me
Me
R = cyclopentyl
104.9
98
96.4
R = cyclohexyl
96
Me
R = Mesityl
Me
88.5
Me
R = Methallyl
85.6
Me
Me
Wick, D. D.; Jones, W. D. Organometallics 1999, 18, 495-505
Compound
Re(Cp)(CO)2(H)(R)

Theory Level
Bond (C-Y)
Energy
R = Ph
F
R=
Ln Re
C-Re
C-H
C-Re
C-H
252.0
489.8
276.9
500.5
C-Re
C-H
253.5
490.6
C-Re
C-H
255.3
494.3
C-Re
C-H
300.0
512.0
C-Re
C-H
278.7
501.2
C-Re
C-H
278.1
500.3
C-Re
C-H
279.9
504.6
C-Re
C-H
255.4
492.0
C-Re
C-H
256.1
494.5
C-Re
C-H
301.2
511.8
C-Re
C-H
302.7
515.5
C-Re
C-H
280.4
501.7
All calculated with

B3PW91 (Hybrid DFT)
R=
R=
Ln Re
Ln Re
R=
LnRe
F
F
R=
LnRe
F
R=
LnRe
F
R=
LnRe
F
F
R=
LnRe
F
F
R=
LnRe
F
F
R=
LnRe
F
F
R=
Ln Re
F
F
F
R=
LnRe
F
Clot, E.; Besora, M.; Maseras, F.; Megret, C.; Eisenstein, O.; Oelckers, B.; Perutz, R. N.
Chem. Commun. 2003, 490-491
Compound
Bond Dissociation Enthalpy (kJ/mol)

Theory Level
Bond (C-Y)
Energy
Re(Cp)(CO)2(H)(R)
R=
LnRe
C-Re
C-H
280.8
503.6
C-Re
C-H
281.0
504.8
C-Re
C-H
257.4
495.0
C-Re
C-H
304.7
512.4
C-Re
C-H
304.0
514.7
C-Re
C-H
283.0
504.4
C-Re
C-H
306.7
514.7
All calculated with

B3PW91 (Hybrid DFT)
R=
Ln Re
F
F
R=
Ln Re
R=
LnRe
F
F
R=
LnRe
R=
F
F
Ln Re
F
F
R=
F
F
F
F
Ln Re
F
RSE
O
N
Me
Me
H
Me
C-H
O
N
6.3
Chem. Commun. 2003, 490-491
(kcal/mol)
92.4
Me
N
O
Brocks, J. J.; Welle, F. M.; Beckhaus, H.-D.; Rchardt, C.Tet. Lett. 1997, 38(44) , 7721-7724
Compound

Solvent
Bond (C-Y)
Energy
77
isooctane
93
isooctane
H
H C OH
H
92
water
OH
92
water
89
water
90
water
99
water
96
water
92
water
78
benzene
77
benzene
Me
C-H
Me
O
Me
Me
H
Me
H
Me
OH
OH
HO
(CH2(-H))3OH
H H
CN
H
H
H
COO-
H
H
Me
Me
Laarhoven, L. J. J.; Mulder, P.; Wayner, D. D. M. Acc. Chem. Res . 1999, 32, 342-349
Compound

Solvent
Bond (C-Y)
Energy
C-H
H
Me
OH
H
N
H
N
77
benzene
77
benzene
69
benzene
78
benzene
94
benzene
93
benzene
92
THF
83
tetralin
O
H
N
N
H
O
H
H
Laarhoven, L. J. J.; Mulder, P.; Wayner, D. D. M.Acc. Chem. Res . 1999, 32, 342-349
H
C-H
CH3
Me
H
Me
H
Me
104.9
101.1
Me
98.6
Me
Me
96.5
H
H
110.7
H
88.8
112.9
H OMe
89.7
104.6
O
H
88.1
O
Me
89.4
Compound
CH3
CH2

Theory Level
Bond (C-Y)
Energy
C-H
H CH
H CN
H
Me
H
H
Me
H
Me
98.6
Et
H
Me
Me
Me
Me
104.99
110.4
101.3
126.3
80.9
101.1
98.2
96.5
110.7
H
133.32
112.9
H
78
94
H
109
H
88.8
H
H
H
89.8
Compound

Theory Level
Bond (C-Y)
Energy
C-H
101.1
Me
H
110.7
35.7
H2C
H
H
83
35.4
H
H
133.32
H
H
86
112.9
78
94
H
109
H

OH
C-H
96.1
H
O
22.0
C O
105
88.0
-12
H
H
H
H
H
O
Compound
Resultant
Radical
CH
HCH
HCH2

Bond Enthalpy Terms (E )
Bond (C-Y)
Energy
C-H
341
426
458
HCH3
439.4
C2H
485
C2H2
555
C2H4
461
C2H6
421
410.8
C3H6
363
410.8
410.8
407.0
410.8
407.0
410.8
403.9
CpH
c -C5H10
418
406
418
406
420
396
347
395
C5H12
418
410.8
Me3CCH3
418
410.8
C6H6
465
420.6
C3H8
C4H10
Me3CH
Pr
i -Pr
Bu
s -Bu
i -Bu
t -Bu
c -C6H12
400
407.0
2,3-Me2Bu
418
410.8
Bz
MeC6H4
368
410.8
PhCCH
PhCH2Me
465
553
357
420.6
435
407.0
c -C5Me5
368
2,3-Me2C4H8
PhCH3
Simes, J.A.M.; Beauchamp, J.L.Chem. Rev. 1990, 90 , 629-688
C-H
Me
N
Me
Me
381
379.5
Experimental
Estimated
381
370.2
Experimental
Estimated
H
Bu
Bu
Et
H
H3C
Cherkasov, A.; Jonsson, M.J. Chem. Inf. Comput. Sci. 2000, 40, 1222-1226
438.56
Compound
Resultant
Radical
BuCH2OH
PhOH
PhC(O)H
CF2H

Bond (C-Y)
Energy
C-H
389
362
371
274
401.7
451.2
426.6
447
359
424
430
381
436
420
CH2F
CH3F
CH2F2
CF3C(O)H
CF3CH2OH
C6F5OH
HCl
HBr
HI
SiH3
362
432.0
366.3
298.4
304
CF3H
SiMe4
HCO
MeCO
EtCO
PrCO
PhCO
Me2CO
MeC(O)Cl
PhC(O)Cl
MeI
C2H3I
EtI
C3H5I
PrI
i -PrI
BuI
PhI
BzI
PhCH2CH2I
Me(CHEt)2PhCCI
Me3SiCH2I
I2
PhC(O)I
MeC(O)I
H
Me
Et
Pr
Ph
MeCO
MeCO
PhCO
C2H3
C3H5
415
63
61
49
46
104
340
340
343
238
272
235
180
235
232
237
273
207
237
237
319
232
MeCO
151.3
212
209
426.6
451.2
451.2
Compound
CH4
Me
H
Me
H
Me
Me
H
Me
H
Me
H

Theory Level
Bond (C-Y)
Energy
C-H
421.1
427.4
439.5
438.9
B3LYP
KMLYP
CBS-Q
Experimental
411.6
419.3
425.5
420.7
B3LYP
KMLYP
CBS-Q
Experimental
465.0
476.6
462.0
464.7
B3LYP
KMLYP
CBS-Q
Experimental
563.3
572.9
557.6
556.1
B3LYP
KMLYP
CBS-Q
Experimental
413.0
424.0
426.9
422.7
B3LYP
KMLYP
CBS-Q
Experimental
394.4
405.4
414.9
416.8
B3LYP
KMLYP
CBS-Q
Experimental
350.9
359.5
361.3
361.9
B3LYP
KMLYP
CBS-Q
Experimental
458.2
468.9
471.7
B3LYP
KMLYP
CBS-Q
436.3
447.7
452.1
B3LYP
KMLYP
CBS-Q
364.1
377.2
380.1
339.0
B3LYP
KMLYP
CBS-Q
Experimental
Senosiain, J. P.; Han, J. H.; Musgrave, C. B.; Golden, D. M.Faraday Discuss. 2001, 119 , 173-189
Reference includes radical stabilization energies
Compound

Theory Level
Bond (C-Y)
Energy
562.2
570.2
566.1
B3LYP
KMLYP
CBS-Q
441.3
452.6
458.5
444.8
B3LYP
KMLYP
CBS-Q
Experimental
406.5
413.8
421.3
379.1
B3LYP
KMLYP
CBS-Q
Experimental
409.8
418.0
427.6
425.4
B3LYP
KMLYP
CBS-Q
Experimental
393.9
404.0
413.0
411.2
B3LYP
KMLYP
CBS-Q
Experimental
383.9
396.4
409.1
404.3
B3LYP
KMLYP
CBS-Q
Experimental
413.9
423.0
427.6
425.2
B3LYP
KMLYP
CBS-Q
Experimental
413.8
422.2
471.2
B3LYP
KMLYP
CBS-Q
415.4
424.6
427.9
B3LYP
KMLYP
CBS-Q
333.9
343.3
347.9
B3LYP
KMLYP
CBS-Q
Me
Me
H
Me
Me
Me
Me
Me
H
Me
H
Me
Me
H
Me
H
C-H
Compound

Theory Level
Bond (C-Y)
Energy
348.1
357.3
360.5
358.2
B3LYP
KMLYP
CBS-Q
Experimental
447.3
459.4
B3LYP
KMLYP
402.1
414.2
408.8
B3LYP
KMLYP
CBS-Q
462.5
471.7
468.3
B3LYP
KMLYP
CBS-Q
357.8
367.2
364.5
358.2
B3LYP
KMLYP
CBS-Q
Experimental
359.9
373.7
355.1
364.8
B3LYP
KMLYP
CBS-Q
Experimental
421.1
429.7
427.5
B3LYP
KMLYP
CBS-Q
425.2
439.0
B3LYP
KMLYP
399.1
411.3
413.8
407.5
B3LYP
KMLYP
CBS-Q
Experimental
401.3
411.3
419.0
403.8
B3LYP
KMLYP
CBS-Q
Experimental
366.2
373.8
376.2
B3LYP
KMLYP
CBS-Q
Me
H
C-H
Me
H
Me
Me
H
Me
Compound

Theory Level
Bond (C-Y)
Energy
C-H
459.0
472.7
467.5
B3LYP
KMLYP
CBS-Q
460.5
472.8
474.0
B3LYP
KMLYP
CBS-Q
413.9
415.9
428.3
B3LYP
KMLYP
CBS-Q
396.6
398.9
B3LYP
KMLYP
Me
394.6
404.9
B3LYP
KMLYP
Me Me
386.6
400.1
404.0
B3LYP
KMLYP
Experimental
439.0
450.8
B3LYP
KMLYP
338.2
348.6
B3LYP
KMLYP
383.0
402.7
B3LYP
KMLYP
325.6
334.5
333.5
347.0
B3LYP
KMLYP
CBS-Q
Experimental
289.9
296.2
318.0
B3LYP
KMLYP
Experimental
415.8
425.9
418.0
B3LYP
KMLYP
Experimental
344.0
358.2
365.3
B3LYP
KMLYP
Experimental
Me
H
Me
Me
H
Me
Me
H
Me
H
Me
Me
H
H
Me
Me
Me
Me
Me
H
Compound
Me

Theory Level
Bond (C-Y)
Energy
C-H
Me
H
H
Me
Me
335.4
350.2
338.9
B3LYP
KMLYP
Experimental
324.9
334.2
323.0
B3LYP
KMLYP
Experimental
386.9
395.1
406.5
403.5
B3LYP
KMLYP
CBS-Q
Experimental
334.1
336.0
347.1
344.3
B3LYP
KMLYP
CBS-Q
Experimental
389.2
389.6
406.4
B3LYP
KMLYP
CBS-Q
329.9
344.4
346.7
B3LYP
KMLYP
Experimental
308.9
318.0
B3LYP
KMLYP
397.9
409.0
399.6
B3LYP
KMLYP
Experimental
446.3
459.3
B3LYP
KMLYP
333.1
342.8
B3LYP
KMLYP
396.7
407.5
B3LYP
KMLYP
296.7
305.5
305.0
B3LYP
KMLYP
Experimental
H
Me
Compound

Theory Level
Bond (C-Y)
Energy
296.6
308.8
305.4
B3LYP
KMLYP
Experimental
462.3
474.0
473.1
B3LYP
KMLYP
Experimental
361.7
371.8
375.7
B3LYP
KMLYP
Experimental
(kJ/mol)
438.9
429.7
Experimental
Estimated
423
420.7
Experimental
Estimated
374
365.6
Experimental
Estimated
420
416.7
Experimental
Estimated
412.5
411.6
Experimental
Estimated
364.8
364.1
Experimental
Estimated
358.2
349.0
Experimental
Estimated
358.2
347.1
Experimental
Estimated
410.9
414.8
Experimental
Estimated
403.8
402.6
Experimental
Estimated
392.9
386.0
Experimental
Estimated
386
396.5
Experimental
Estimated
387
392.2
Experimental
Estimated

H
C-H
CH3
Me
Me
H
Me
Me
H
Me
H
Me
H
Me
Me
H
Me
H
Me
Me
Me
H
NC
H
Me
NH
Me
H
Me
Compound

Theory Level
Bond (C-Y)
Energy
C-H
394.6
404.6
Experimental
Estimated
370.3
381.9
Experimental
Estimated
357.3
372.8
Experimental
Estimated
353.1
363.8
Experimental
Estimated
376.1
377.0
Experimental
Estimated
361.9
367.9
Experimental
Estimated
392.9
390.4
Experimental
Estimated
384.9
387.4
Experimental
Estimated
446.4
441.9
Experimental
Estimated
361.9
350.7
Experimental
Estimated
347.7
356.6
Experimental
Estimated
403.8
407.5
Experimental
Estimated
345.2
341.7
Experimental
Estimated
347
335.8
Experimental
Estimated
319.7
330.0
Experimental
Estimated
365.3
355.1
Experimental
Estimated
Me
H
Me
Me
H
NC
Me
NC
Me
H
Me
H
HS
H
Me
F 3C
H
H
Me
H
Me
H
H
Me
Me
Compound

Theory Level
Bond (C-Y)
Energy
Me
H
Me
Me
C-H
H
Me
Me
Me
Me
Me
H
Me
Me
Me
H
Me
Me
Me
Me
Me
Me
Me
Me
338.9
347.6
Experimental
Estimated
323
332.6
Experimental
Estimated
403.5
404.1
Experimental
Estimated
418
408.8
Experimental
Estimated
404
398.6
Experimental
Estimated
344.3
346.0
Experimental
Estimated
326.4
342.1
Experimental
Estimated
319.2
329.0
Experimental
Estimated
340.6
334.1
Experimental
Estimated
339
325.0
Experimental
Estimated
411.3
401.0
Experimental
Estimated
386.2
392.0
Experimental
Estimated
389
396.1
Experimental
Estimated
383.7
382.8
Experimental
Estimated
401.9
400.6
Experimental
Estimated
389
391.6
Experimental
Estimated
Me
O
H
Me
O
H
Me
Me
H
Me
Me
H
O
Me
H
HO
Me
H
HO
Compound
Me

Theory Level
Bond (C-Y)
Energy
381
382.6
Experimental
Estimated
423.8
433.8
Experimental
Estimated
431.8
437.9
Experimental
Estimated
421.7
424.4
Experimental
Estimated
421.3
428.4
Experimental
Estimated
413.8
415.0
Experimental
Estimated
421.7
420.3
Experimental
Estimated
411.7
410.9
Experimental
Estimated
392.5
401.5
Experimental
Estimated
425.1
421.4
Experimental
Estimated
417.2
413.1
Experimental
Estimated
401.7
404.9
Experimental
Estimated
431
430.5
Experimental
Estimated
431
431.3
Experimental
Estimated
416.3
428.8
Experimental
Estimated
429.7
432.3
Experimental
Estimated
Me
H
C-H
HO
H H
H
F
F
H
H
F
Cl
H
H
F
F
Cl
H
F
Cl
Cl
H
F
Cl
H
H
H
Cl
H
H
Cl
Cl
Cl
H
Cl
Br
Br
Br
Br
Br
H
Br
H H
I
I
Me
F
F3C
Compound
Cl

Theory Level
Bond (C-Y)
Energy
C-H
H
H
425.9
414.8
Experimental
Estimated
F 3C
Cl
Cl
H
Cl
Cl
H
393
393.1
Experimental
Estimated
Cl
Cl
Cl
Cl
Cl
H
397
388.7
Experimental
Estimated
Cl
Br
404.2
406.2
Experimental
Estimated
435
429.2
Experimental
Estimated
433.5
422.7
Experimental
Estimated
415.1
415.1
Experimental
Estimated
383.7
390.3
Experimental
Estimated
407
394.9
Experimental
Estimated
388
400.8
Experimental
Estimated
388
386.4
Experimental
Estimated
384
395.4
Experimental
Estimated
385
381.2
Experimental
Estimated
385
374.3
Experimental
Estimated
389
374.5
Experimental
Estimated
377
383.8
Experimental
Estimated
F
F
F
F
F
F
Me
Me Si
Me
O
Me
H
Me
O
H
HO
H
H2N
H
H2N
Me
Me
H
H2N
Me
N
H
H
N
N
H
O
N
H
H
N
Compound
C-H
416.6
422.6
ab-initio
Experimental
370.7
375.9
ab-initio
Experimental
419.4
423.1
ab-initio
Experimental
405.2
406.6
ab-initio
Experimental
375.4
375.4
ab-initio
Experimental
426
ab-initio
397.8
390.6
ab-initio
Experimental
CH3
378.0
365.1
ab-initio
Experimental
Cl
407.3
ab-initio
375.8
365.4
ab-initio
Experimental
419.4
423.3
ab-initio
Experimental
407.8
409.1
ab-initio
Experimental
371.5
371.2
ab-initio
Experimental
H
H3C
H3C

Theory Level
Bond (C-Y)
Energy
CH3
H
Cl
Cl
H
Me
Cl
H3C
Cl
Cl
H
Me
Cl
Cl
Cl
Cl
Cl
H
Cl
Cl
H
Me
Me
H
Me
CH3
Me
Compound

Theory Level
Bond (C-Y)
Energy
418.7
ab-initio
406.5
409.3
ab-initio
Experimental
407.0
407.0
ab-initio
Experimental
Cl
345.3
354.5
ab-initio
Experimental
Cl
376.5
371.4
ab-initio
Experimental
Cl
378.2
370.4
ab-initio
Experimental
420.0
ab-initio
401.5
ab-initio
347.8
352.9
ab-initio
Experimental
376.3
367.5
ab-initio
Experimental
C-H
Cl
H
Cl
Me
Cl
Me
Me
H3C
Me
Me
Cl
Me
Me
H
Cl
Me
Cl
Me
Cl
H3 C
Me
C-H
357
Ling, Y.; Lifshitz, C. J. Mass Spec. 1997, 32 , 1219-1225
453.5
359.9 20
Compound
H3C

Theory Level
Bond (C-Y)
Energy
C-H
112.3
102.0, 102.2
DFT-AM1
Experimental
108.0
98.0, 98.3
DFT-AM1
Experimental
105.2
95.0, 95.7
DFT-AM1
Experimental
102.3
92.0, 93.1
DFT-AM1
Experimental
139.0
125.0, 126.4
DFT-AM1
Experimental
120.0
108.0, 109.2
DFT-AM1
Experimental
91.3
86.6, 83.1
DFT-AM1
Experimental
94.1
87.9, 85.6
DFT-AM1
Experimental
99.6
89.0, 90.6
DFT-AM1
Experimental
115.7
106.3, 105.2
DFT-AM1
Experimental
104.1
96.5, 94.7
DFT-AM1
Experimental
100.6
94.5, 91.5
DFT-AM1
Experimental
105.2
95.5, 95.7
DFT-AM1
Experimental
103.5
92.5, 94.2
DFT-AM1
Experimental
86.4
81.2, 78.6
DFT-AM1
Experimental
117.7
110.2, 107.1
DFT-AM1
Experimental
H
Me
Me
Me
Me
Me
Me
H
NC
Compound
NC

Theory Level
Bond (C-Y)
Energy
C-H
133.0
120.0, 121.0
DFT-AM1
Experimental
99.0
87.0, 90.1
DFT-AM1
Experimental
98.8
86.0, 89.9
DFT-AM1
Experimental
102.4
93.0, 93.2
DFT-AM1
Experimental
83.3
85.6
Calculated
Experimental
79.9
78.9
Calculated
Experimental
88.3
Calculated
84.6
86.6
Calculated
Experimental
O
Me
H
Me
C-H
H
H
H
Glasovac, Z.; Eckert-Maksic, M.; Dacres, J. E.; Kass, S. R.J. Chem. Soc. Perkin Trans. 2 2002, 2 , 410-415
H3C
C-H
H
Me
Me
H
Me
Me
Me
H
Me
FH2C
Korth, H.-G.; Sicking, W. J. Chem. Soc. Perkin Trans. 2 1997, 715-719
79.4
100.3
105.8
104.7, 104.9
HF
MP2
B3LYP
Experimental
76.8
98.9
101.1
100.2, 101.1
HF
MP2
B3LYP
Experimental
74.5
95.3
97.1
99.4, 98.6
HF
MP2
B3LYP
Experimental
72.7
93.7
94.0
95.2, 96.5
HF
MP2
B3LYP
Experimental
77.8
96.0
99.1
101.7
HF
MP2
B3LYP
Experimental Avg
Compound
ClH2C

Theory Level
Bond (C-Y)
Energy
C-H
76.6
95.0
99.7
101.5
HF
MP2
B3LYP
Experimental Avg
74.1
92.3
95.2
94.1, 96.1
HF
MP2
B3LYP
Experimental
67.5
85.0
87.7
92.2
HF
MP2
B3LYP
Experimental Avg
74.9
93.1
96.3
94.1
HF
MP2
B3LYP
Experimental Avg
H
HO
H2N
HS
69.8
96.2
93.8
92.6, 94.8, (93.4)
H
NC
O
H
Me
O
H
Me
O
H
HO
O
Me
S
O
Cl3C
HF
MP2
B3LYP
Experimental (Avg)
67.3
93.5
93.4
94.2
HF
MP2
B3LYP
Experimental Avg
69.4
94.4
94.0
95.1
HF
MP2
B3LYP
Experimental Avg
73.7
95.2
97.2
96.0
HF
MP2
B3LYP
Experimental Avg
80.8
101.2
103.4
99.0
HF
MP2
B3LYP
Experimental Avg
71.8
89.4
92.0
95.6
HF
MP2
B3LYP
Experimental Avg
Compound

Theory Level
Bond (C-Y)
Energy
106.6
106.7
MP2/cc-pVtz (298K)
Experimental
94.7
95.8
MP2/cc-pVtz (298K)
Experimental
Br3C
93.2
96
MP2/cc-pVtz (298K)
Experimental
H 3C
104.4
105.1
MP2/cc-pVtz (298K)
Experimental
FH 2C
101.2
101.3
MP2/cc-pVtz (298K)
Experimental
ClH2C
99.4
99.5
MP2/cc-pVtz (298K)
Experimental
BrH2C
98.9
101.6
MP2/cc-pVtz (298K)
Experimental
F2HC
101.5
102.3
MP2/cc-pVtz (298K)
Experimental
Cl2HC
95.3
95.6
MP2/cc-pVtz (298K)
Experimental
Br2HC
97.8
99.7
MP2/cc-pVtz (298K)
Experimental
F 3C
Cl3C
C-H
McGivern, S. W.; Derecskei-Kovacs, A.; North, S. W.; Francisco, J. S.J. Phys Chem. A, 2000, 104 , 436
(kJ/mol)
Polycyclic Aromatic Hydrocarbon Borders
C-H
Zigzag border
Armchair border
Second Armchair dissociation
~480
~477
~361
May, K.; Dapprich, S.; Furche, F.; Unterreiner, B. V.; Ahlrichs, R.Phys. Chem. Chem. Phys. 2000, 2 , 5084-5088
H
Me
Cl3C
c-C6H7
C-H
(kcal/mol)
84.8, 85.7
87
DFT
Experimental
92.1
96
DFT
Experimental
71.4, 72.3
77
DFT
Experimental
87.8, 88.6
90
DFT
Experimental
Kranenburg, M.; Ciriano, M. V.; Cherkasov, A.; Mulder, P.J. Phys. Chem. A 2000, 104 , 915-921
Compound

Theory Level
Bond (C-Y)
Energy
C-H
c-C6H11
c-C6H7
c-C4H 8N
N(Et)2CHCH 3
C4 H7O
C4H7O2
97
Photoacoustic Calorimetry
77
88.2, (87)
DFT, (Expt)
89.9, 89
DFT, (Expt)
90.7, 91.6, (92)
DFT, (Expt)
94.6, (96)
DFT, (Expt)
H3C
105.0, 105.7
105
DFT
Experimental
C2 H5
100.3, 101.0
101
DFT
Experimental
C3 H7
100.9, 101.6
101
DFT
Experimental
96.4, 97.1
98
DFT
Experimental
93.2, 94.0
96
DFT
Experimental
Me
Me
H
Me
Me
H
c-C3H5
106.4, 107.2
DFT
c-C4H7
97.3, 98.0
DFT
c-C6H11
96.9, 97.6
97
DFT
Experimental
109.3
111
DFT
Experimental
105.7
DFT
110.8
113
DFT
Experimental
85.0, 85.9
88
DFT
Experimental
80.2, 81.5
84
DFT
Experimental
C2 H3
Me
H
Me
H
Compound

Theory Level
Bond (C-Y)
Energy
O
C-H
H2 N
H
91.3
ALL ab-initio
O
HO
H
91.5
O
Me
H
O
H
H
O
F
91.5
91.6
91.8
O
HOOC
H
O
F3C
92.0
92.0
O
NC
92.2
H
O
O2N
H
92.2
O
H
O
Me
H
O
88.4
G3
89.4
89.3
G3
Experimental
91.2
G3
91.6
88.9
CBS-4M
Experimental
O
H
Compound

Theory Level
Bond (C-Y)
Energy
107.1
108.0
108.1
109.2
IB method
Experimental
Cl
79.6
81.4
80.0
83.2
IB method
Experimental
Br
65.8
70.6
69.7
69.5
69.1
70.9
corrected MP2/cc-pVdz
corrected MP2/cc-pVqz
IB method
Experimental
H3 C
H3C
H3 C
C-X
CH2 F
C-X
CHF2
C-H
CH2Cl
Cl
C-X
CHCl2
C-H
CH2Br
Br
C-X
CHBr2
C-H
CHF2
CF3
C-H
CHCl2
CCl3
Cl
Br
H
C-X
C-H
CHBr2
CBr3
C-X
C-X
C-H
119.3
118.8
100.0
101.3
Experimental
Experimental
78.5
80.9
93.8
95.6
Experimental
Experimental
67.0
69.8
96.3
99.7
Experimental
Experimental
127.8
127.0
105.1
106.7
Experimental
Experimental
75.6
77.8
93.2
95.8
Experimental
Experimental
63.8
66
93.2
96
Experimental
Experimental
Compound
C5 H11

Theory Level
Bond (C-Y)
Energy
C-Cl
Cl
352.5
C-X
(kcal/mol)
87
(solvent)
benzene
61
various
Cl
Br
H3 C
H3C
Cl
H 3C
Br
H 3C
C-X
115
83.7
72.1
57.6

H3 C
H3C
Cl
H 3C
Br
C-X
(kJ/mol)
459.69
350.7
291.8
Compound
H3 C

Theory Level
Bond (C-Y)
Energy
C-F
115
Me
Me
110.6
F
F
123.3
F
127.2
F
98.7
O
Me
122.2
F

H3C
C-Cl
Cl
CH3
Cl
Me
85.2
Me
Cl
Me
83.7
84.8
84.9
Me
Me
Cl
Cl
91.2
Cl
97.1
Cl
74
O
Me
84.7
Cl

H3 C
C-Br
Br
72.1
CH3
Br
72.4
Me
Me
Br
Me
73.9
Me
Me
72.6
Br
Br
80.8
Br
Br
Br
O
Me
59
84
63
71.7
Br
Compound
H 3C

Theory Level
Bond (C-Y)
Energy
C-I
CH 3
57.6
56.9
I
Me
57
Me
I
Me
Me
Me
55.6
I
I
45.6
I
67
I
51
O
Me
53.8
109.7
109.8
MP2/cc-pVtz (298K)
Experimental
Cl
83.0
83.8
MP2/cc-pVtz (298K)
Experimental
Br
71.2
70.9
MP2/cc-pVtz (298K)
Experimental
H3C
H 3C
H3C
C-X
FH2C
120.7
119.4
MP2/cc-pVtz (298K)
Experimental
ClH2C
Cl
80.0
80.9
MP2/cc-pVtz (298K)
Experimental
BrH2C
Br
68.2
69.8
MP2/cc-pVtz (298K)
Experimental
F 2HC
Fluoroform
129.1
127.6
MP2/cc-pVtz (298K)
Experimental
Cl2HC
Cl
Chloroform
76.6
78.4
MP2/cc-pVtz (298K)
Experimental
Br2HC
Br
Bromoform
64.6
66
MP2/cc-pVtz (298K)
Experimental
McGivern, S. W.; Derecskei-Kovacs, A.; North, S. W.; Francisco, J. S.J. Phys Chem. A, 2000, 104 , 436
Compound
H 3C
Br
F3C
Br

Theory Level
Bond (C-Y)
Energy
C-X
73.6
74.0
73.8
70.0
G2
G2MP2
G2MS
Experimental
74.8
75.1
74.8
70.6
G2
G2MP2
G2MS
Experimental
426.1, 461.9
LLM Method
Cl
354.9, 354.8
LLM Method
Br
312.9, 313.4
LLM Method
CH3
CH 3
CH3
C-X
H3C
F
451.5
473.7
Experimental
LLM Method
Cl
350.2
356.8
Experimental
LLM Method
290.8
311.3
Experimental
LLM Method
231.4
Experimental
H3C
H3C
Br
H3C
I
412.8
416.6, 417.1
Experimental
LLM Method
299.9
299.6, 296.2
Experimental
LLM Method
239.3
256.5, 257.7
Experimental
LLM Method
Cl
Br
187.8
Verevkin, S. P.; Krashnykh, E. L.; Wright, J. S.Phys. Chem. Chem. Phys. 2003, 5 , 2605-2611
Experimental
Compound

Theory Level
Bond (C-Y)
Energy
C-X
453.1
482.5
Experimental
LLM Method
346.4
358.9
Experimental
LLM Method
Br
291.6
310.3
Experimental
LLM Method
227.2
Experimental
425.1
LLM Method
292.4
297.8
Experimental
LLM Method
240.1
250.8
Experimental
LLM Method
176.1
Experimental
Me
F
Me
Me
Cl
Me
Me
Me
Me
Me
F
Me
Cl
Me
Br
Me
I
Me
Me
Me
Me
483.7
LLM Method
Me
Me
Me
Cl
351.6
359.0
Experimental
LLM Method
Me
Me
Me
Br
292.4
304.2
Experimental
LLM Method
Me
Me
Me
226.9
Experimental
434.0
LLM Method
292.8
294.8
Experimental
LLM Method
236.7
243.6
Experimental
LLM Method
176.0
Experimental
F
Me
Me
Cl
Me
Me
Br
Me
Me
I
Me
Me
Verevkin, S. P.; Krashnykh, E. L.; Wright, J. S.Phys. Chem. Chem. Phys. 2003, 5 , 2605-2611
Compound

Theory Level
Bond (C-Y)
Energy
C-F
O
H
120.6
G3
122.2
G3
121.7
G3
121.5
CBS-4M
83.0
G3
84.6
84.6
G3
Experimental
84.5
G3
87.8
CBS-4M
F
O
Me
O
F
O
F
O
H
C-Cl
Cl
O
Me
Cl
O
Cl
O
Cl
C-F
H2 N
F
O
HO
F
O
H3 C
121.7
121.6
121.6
F
O
H
F
O
F
121.5
121.4
F
O
121.4
HOOC
F
O
F 3C
121.4
F
O
NC
121.3
F
O
O2N
F
121.2
Compound

Theory Level
Bond (C-Y)
Energy
O
C-Cl
88.3
H2 N
ALL ab-initio
Cl
O
88.0
HO
Cl
O
88.0
H3 C
Cl
87.8
H
Cl
O
F
87.7
Cl
87.6
HOOC
Cl
O
87.6
F 3C
Cl
87.5
NC
Cl
O
87.4
O2N
Cl
Cl
Me
H
Me
Cl
Cl
Cl
Cl
C-Cl
340.3
354.1
ab-initio
Experimental
324.5
327.9
ab-initio
Experimental
338.9
345.1
ab-initio
Experimental
Compound

Theory Level
Bond (C-Y)
Energy
R = Li
R-Cp
82.3
79.0
58.6
54.4
57.9
50.4
55.3
50.4
60.0
56.1
87.3
94.5
87.4
88.4
78.3
79.2
78.0
76.7
66.0
67.0
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
R-(Cp)2
153.9
146.6
154.0
146.3
121.1
112.5
121.0
112.5
154.9
155.2
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
R-(Cp)2
149.3
145.3
161.1
154.3
69.6
60.9
124.3
131.0
117.4
123.4
111.3
116.0
106.2
107.9
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
CCSD(T)/B//BP86/A
BP86/A
R = Na
R=K
R = Rb
R = Cs
R=B
R = Al
R = Ga
R = In
R = Tl
R = Be (D5d)
R
R = Be (Cs)
R = Mg (D5d)
R = Mg (D5h)
R = Ca (D5d)
R = Sr (C1)
R
R = Ba (Cs)
R = Zn (Cs)
R = Si (C 2)
R = Ge (Cs)
R = Sn (Cs)
R = Pb (C1)
Chem. Eur. J. 2002, 8(20), 4693-4707.
Compound

Theory Level
Bond (C-Y)
Energy
M = Fe
Fe(py )+
Fe(py )+
Fe(bz)
Arene-M
207.5
239.2
235.8
Threshold-CID
m -PW1PW91
B3LYP
M = Fe
223.7
209.2
206.7
Threshold-CID
Kinetics Method
Kinetics Method
M = Fe
228.6
255.1
m -PW1PW91
B3LYP
M = Fe
186.0
185.7
m -PW1PW92
B3LYP
M N
Fe(py )+
M
N
Helvet. Chim. Acta 2003, 86 , 1008-1025
Benzene-M
M
Toluene-M
M = Cr+
M = Fe+
M = Co+
Arene-M
40.6
49.6
61.1
M = Cr+
M = Fe+
M = Co+
42.6
51.8
63.4
M = Cr+
M = Fe+
M = Co+
43.5
52.9
64.2
M = Cr+
M = Fe+
M = Co+
44.3
53.6
65.2
M = Cr+
M = Fe+
M = Co+
44.3
53.9
65.3
Ethylbenzene-M
Et
o -xylene-M
m -xylene-M
M
Eur. J. Org. Chem. 1998, 565-571
Compound
p- xylene-M
M
Mesitylene-M
M
1,2,4-trimethylbenzene-M
M
Durene-M
M
Pentamethylbenzene-M
M
Hexamethylbenzene-M
M
Phenol-M
M
OH
Fluorobenzene-M
M
Chlorobenzene-M
M
M = Cr+
M = Fe+
M = Co+

Theory Level
Bond (C-Y)
Energy
Arene-M
44.3
53.8
65.3
M = Cr+
M = Fe+
M = Co+
45.9
55.2
66.8
M = Cr+
M = Fe+
M = Co+
45.7
55.3
66.9
M = Cr+
M = Fe+
M = Co+
47.1
56.6
68.2
M = Cr+
M = Fe+
M = Co+
48.2
57.8
69.7
M = Cr+
M = Fe+
M = Co+
49.0
58.9
70.9
M = Cr+
M = Fe+
M = Co+
41.0
50.0
61.0
M = Cr+
M = Fe+
M = Co+
36.2
45.1
56.2
M = Cr+
M = Co+
37.1
57.4
Cl
Eur. J. Org. Chem. 1998, 565-571
Compound
Bromobenzene-M
M = Co+

Theory Level
Bond (C-Y)
Energy
Arene-M
58.4
M
Br
Iodobenzene-M
M = Co+
60.1
M = Cr+
M = Fe+
M = Co+
38.8
47.8
58.8
m -fluorotoluene-M M = Cr+
M
M = Fe+
F
M = Co+
38.5
47.4
58.6
p -fluorotoluene-M
M = Cr+
M = Fe+
M = Co+
38.5
47.7
58.6
M = Co+
59.7
m -chlorotoluene-M M = Co+
59.6
M
I
o -fluorotoluene-M
M
F
M
F
o -chlorotoluene-M
M
Cl
M
Cl
p -chlorotoluene-M
M = Co+
59.6
M = Cr+
M = Fe+
M = Co+
44.8
54.0
64.8
M = Cr+
M = Fe+
M = Co+
47.0
47.8
57.8
M
Cl
Aniline-M
M
NH2
Benzonitrile-M
M
CN
Eur. J. Org. Chem. 1998, 565-571
Compound
F3B
Cl3B
F3Al
Cl3Al
F3Ga
Cl3Ga
F3In
Cl3In
F4Ti
Cl4Ti

Theory Level
Bond (C-Y)
Energy
R = CO
R = C(NH2)2
R = CO
R = C(NH2)2
R = CO
R = C(NH2)2
R = CO
R = C(NH2)2
R = CO
R = C(NH2)2
R = CO
R = C(NH2)2
R = CO
R = C(NH2)2
R = CO
R = C(NH2)2
R = CO
R = C(NH2)2
R = CO
R = C(NH2)2
M-R
2.5
39.8
1.8
56.7
13.7
55.5
12.8
59.1
11.3
56.8
8.6
55.1
13.0
57.5
10.9
55.4
35.7
21.2
2.9
39.0
Eur. J. Inorg. Chem. 1999, 2037-2045
Cr(CO)5L
L
OC
CO
M
OC
CO
CO
L = OH2
L = OC
L = CO
(staggered C2v)
L = NH3
L = PH3
L = PMe3
L = N2
L = CF2
(staggered C2v)
L = CCl2
L = CS
(staggered C2v)
L = CH2
(eclipsed C2v)
L = CH2
L = NO+
Mo(CO)5L
L = OH2
L = OC
L = NH3
L = PH3
L = PMe3
L = N2
L = CO
van Wuellen, C. J. Comp. Chem. 1997, 18(16), 1985-1992
Cr-COax
Cr-COax
Cr-L
Cr-COax
Cr-L
Cr-COax
Cr-L
Cr-COax
Cr-L
Cr-COax
Cr-L
Cr-COax
Cr-L
Cr-COax
Cr-COax
Mo-COax
Mo-L
Mo-COax
(kJ/mol)
242
230
183
183
233
213
214
205
211
177
223
166
249
167
344
164
341
166
150
253
242
231
199
194
202
163
163
MP2/II+//MP2/II
Compound
Mo(CO)5L
L
OC
CO
M
OC
CO
CO

Theory Level
Bond (C-Y)
Energy
L = CF2
(staggered C2v)
L = CCl2
(staggered C2v)
L = CS
L = CH2
W(CO) 5L
(staggered C2v)
L = NO+
L = OH2
L = OC
L = NH3
L = PH3
L = PMe3
L = N2
L = CO
L = CF2
(staggered C2v)
L = CCl2
(staggered C2v)
L = CS
L = CH2
(staggered C2v)
L = NO+
Cr(CO)5L
L = CH2
Mo-L
Mo-COax
Mo-L
Mo-COax
Mo-L
Mo-COax
Mo-L
Mo-COax
Mo-COax
W-COax
W-COax
W-COax
W-COax
W-COax
W-COax
W-L
W-COax
W-L
W-COax
W-L
W-COax
W-L
W-COax
W-L
W-COax
W-L
W-COax
191
153
205
142
228
142
321
128
140
293
278
269
233
227
233
193
193
224
184
239
173
264
173
362
159
456
165
Cr-L
344
351
353
211
180
223
223
L = CF2
L = CCl2
Mo(CO)5L
L = CH2
Mo-L
L = CF2
L = CCl2
W(CO) 5L
L = CH2
L = CF2
L = CCl2
van Wuellen, C. J. Comp. Chem. 1997, 18(16), 1985-1992
W-L
321
335
353
191
162
228
362
380
380
224
199
239
QR-DFT
CCSD(T)//MP2
MP2
QR-DFT
CCSD(T)//MP2
MP2
QR-DFT
CCSD(T)//MP2
MP2
Compound

Theory Level
Bond (C-Y)
Energy
o
H
Zn-C
374
ZnMe2
ZnEt2
312
ZnPr2
337
ZnBu2
334
Smith, D. W. J. Organomet. Chem. 1999, 585, 150-153
U( -C5Me5)2R2
U-Rn
R = Me
R = CH2Ph
244
R = CH2SiMe3
307
U( -C5Me5)2R(Cl)
R = Me
R = CH2Ph
R = Ph
U(5-C5Me5)2(OSit BuMe2)(R)
R = Me
R=H
U{5-C5H4(SiMe3)}3R
U(5-C5H4t Bu)3R
U(C9H7)3R
300
312
263
358
317
342
R = Me
R = Bu
R = CH2SiMe3
185
152
168
R = CH2Ph
149
R = CHCH2
R = C C Ph
R=I
R = SEt
t
R = S Bu
R=H
R=H
R=I
R = SEt
R = Me
R = OCH2CF3
R=I
223
363
262, 265.6
266
158
253.7
251.6
246.3
252
195
301
267
Ta(CH2SiMe3)5
(alkilydene formation)
D1
Ta-C
Ta-C
Ta=C
(kcal/mol)
44
67
126
Ta-C
261
Luo, L.; Li, L.; Marks, T.J. J. Am. Chem. Soc. 1997, 119, 8574-8575
TaMe5
237
Compound
U(C9H6Et)3R
U(C9H6SiMe3)3R
U(5-C5H5)3R
UR2

Theory Level
Bond (C-Y)
Energy
R = Me
U-Rn
R = SEt
R = SiPh3
156
R = GePh3
163
R = SnPh3
156
R = Fe(CO)2(cp)
129
R = Ru(CO)2(cp)
R = Cp
R = C8H8
169
299
344
442
190
417
R = C8H7Bu
UR4
Me2
UCl2R(Tp
)3
UCl2R(TpMe2)3.thf
187
R = MeCO2
R = Cl
R = CH(SiMe3)2
R = Cp
t
R = O Bu
R = OCMe2CH2COMe
158
517
422.6
295
362
460.5
484.2
R = N(SiMe3)2
334
R = (3,5-Me2pz
293
R = Thf
21.5
Compound
RMe3

Theory Level
Bond (C-Y)
Energy
R = Si
C-Me
70.62
70.46
89.30
89.12
86.37
86.19
HF and NR
HF and RESC
B3LYP and NR
B3LYP and RESC
BOP and NR
BOP and RESC
R = Ge
62.99
62.20
80.73
77.78
77.67
76.55
HF and NR
HF and RESC
B3LYP and NR
B3LYP and RESC
BOP and NR
BOP and RESC
R = Sn
53.22
51.30
71.41
68.84
68.91
66.15
HF and NR
HF and RESC
B3LYP and NR
B3LYP and RESC
BOP and NR
BOP and RESC
R = Pb
46.09
39.87
64.57
56.32
62.28
53.49
HF and NR
HF and RESC
B3LYP and NR
B3LYP and RESC
BOP and NR
BOP and RESC
M = Ru
M = Rh
M = Pd
110.2
114.6
113.9
GGA-BP86 XC
GGA-BP86 XC
GGA-BP86 XC
M = Ru
M = Rh
M = Pd
67.1
67.4
58.2
GGA-BP86 XC
GGA-BP86 XC
GGA-BP86 XC
Lie, W.; Fedorov, D. G.; Hirao, K.J. Phys. Chem. A 2002, 106, 7057-7061
M
Sn
M
Pd
CH2
CF2
Xavier, E. S.; Duarte, H. A.J. Quant. Chem. 2003, 95(2) , 164-176
Compound
Cu
C(2)
Ni
C(1)
Ni
C(3)
Fe
C(3)
Fe
C(5)
Ti
C(3)
Ti
C(5)
Cu
CO(2)
Ni
CO(1)
Ni
CO(3)
Fe
CO(3)
Fe
CO(5)
Ti
CO(3)
Ti
CO(5)

Theory Level
Bond (C-Y)
Energy
MC Bond Distance ()
1.799
1.624
1.625
1.565
1.628
1.679
1.829
MC ()
1.903
1.661
1.861
1.698
1.864
2.013
2.034
Cu5C(2)(4,1)
Ni5C(1)(5,0)
Ni5C(1)(4,1)
Ni5C(3)(5,0)
Ni5C(3)(4,1)
Fe5 C(3)(4,1)
Fe5 C(5)(4,1)
Ti7C(3)(7,0)
Ti7C(5)(7,0)
Cu 5CO(2)(4,1)
Ni5CO(1)(5,0)
Ni5CO(1)(4,1)
Ni5CO(3)(5,0)
Ni5CO(3)(4,1)
Fe5CO(3)(4,1)
Fe5CO(5)(4,1)
Ti7CO(3)(7,0)
Ti7CO(5)(7,0)
M-C BDE
15.4
61.4
27.5
47.1
39.6
27.7
44.4
MC ()
1.750
0.05
1.625
1.65
0.50
0.40
1.82
1.79
Cu5C(2)(5,0)
Cu 5CO(2)(5,0)
CO ()
1.160
1.167
1.164
1.173
1.166
1.171
1.171
M-C
MC ()
1.975
1.70
1.70
.0.02
1.75
0.05
1.05
0.90
2.00
2.05
CO ()
1.160
1.15
1.17
1.23
1.17
1.22
1.22
1.25
1.16
1.19
BDE
90.3
141.4
131.2
155.6
138.0
148.6
126.7
C-O BDE
228.2
223.1
199.5
194.6
204.7
182.2
220.7
M-C BDE
93.7
157.4
145.8
183.8
149.3
189.4
186.0
189.9
129.9
139.5
M-C BDE
6.03
3.03
22.55
26.16
28.02
13.65
17.86
46.24
33.16
40.95
Sosa, R. M.; Gardiol, P.; Beltrame, G.J. Quant. Chem. 1997, 65(5) , 919-928
C-O BDE
215.3
148.6
179.7
145.3
181.6
127.2
134.8
159.3
206.3
204.4
Compound
Ti(Cp)2R2

Theory Level
Bond (C-Y)
Energy
R = Me
R = Ph
Ti-Cp
Me
R=
R=
R=
R=
342
341
Me
340
CF3
OMe
349
R = Fe
Mo(Cp)2R2
R=H
R = Me
W(Cp) 2R2
R=H
R = Me
298
331
331
Mo-Cp
251
166
305
221
Calhorda, M. J.; Dias, A. R.; da Piedade, M. E. M.; Salema, M. S.; Simoes, J. A. M.

Organometallics 1987, 6, 734-738
M(CO)4
M = Ni
M = Pd
M = Pt
1.827
1.821
1.825, 1.817
2.016
2.016
1.981
1.976
Doerr, M.; Frenking, G. Z. Anorg. Allg. Chem. 2002, 628 , 843-850
M-CO
(kcal/mol)
26.3
27.0
25 2
12.9
11.7
14.2
13.5
All ZPE corrected

BP86/II
BP86/TZP
Experimental
BP86/II
BP86/TZP
BP86/II
BP86/TZP
Compound
Fe(CO)4R

Theory Level
Bond (C-Y)
Energy
All singlet states, ZPE corrected
Fe-R D3h
39.0
B3LYP/II//B3LYP/II
45.1
CCSD(T)/II//B3LYP/II
R = CO
R = CS
R = N2
R = NO
R = CN
R = NC
axial
C3v
equatorial
C2v
axial
C2v
equatorial
C2v
axial
C3v
equatorial
C2v
axial
C3v
equatorial
C2v
axial
C3v
equatorial
C2v
2
R = -C2H4 axial
equatorial
2
R = -C2H2 axial
Cs
C2v
Cs
Yu, C.; Hartmann, M.; Frenking, G.Z. Anorg. Allg. Chem. 2001, 627 , 985-998
55.8
64.2
55.4
64.2
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
16.5
22.9
15.3
22.4
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
79.2
84.8
92.4
105.1
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
87.0
96.5
81.0
89.9
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
70.7
78.6
64.2
72.7
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
18.3
30.6
25.9
39.2
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
16.9
26.9
B3LYP/II//B3LYP/II
Compound
Fe(CO)4R
R = -C2H2 equatorial
R = CCH2
R = CH2
R = CF2
R = NH3
R = NF3
R = PH3
R = PF3
2
R = -H2

Theory Level
Bond (C-Y)
Energy
All singlet states, ZPE corrected
Fe-R C2v
25.4
B3LYP/II//B3LYP/II
37.3
axial
Cs
equatorial
C2v
axial
Cs
equatorial
C2v
axial
Cs
equatorial
C2v
axial
Cs
equatorial
Cs
axial
Cs
equatorial
Cs
axial
C3v
equatorial
Cs
axial
C3v
equatorial
Cs
axial
Cs
equatorial
C2v
Yu, C.; Hartmann, M.; Frenking, G.Z. Anorg. Allg. Chem. 2001, 627 , 985-998
64.7
75.7
70.3
83.8
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
69.1
79.6
75.1
87.4
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
52.2
59.8
55.2
64.3
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
29.9
39.1
23.7
33.1
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
15.3
23.5
12.2
20.9
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
26.8
38.9
25.9
36.5
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
34.1
45.2
34.5
44.1
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
10.3
16.5
12.8
18.5
B3LYP/II//B3LYP/II
B3LYP/II//B3LYP/II
Compound
5
Re( -C5H5)(CO)2(H)(R)

Theory Level
Bond (C-Y)
Energy
R = Phenyl
Re-R
Re-H
252.0
489.8
Re-R
Re-H
276.9
500.5
Re-R
Re-H
253.5
490.6
Re-R
Re-H
255.3
494.3
Re-R
Re-H
300.0
512.0
Re-R
Re-H
278.7
501.2
Re-R
Re-H
278.1
500.3
Re-R
Re-H
279.9
504.6
Re-R
Re-H
255.4
492.0
Re-R
Re-H
256.1
494.5
Re-R
Re-H
301.2
511.8
Re-R
Re-H
302.7
515.5
Re-R
Re-H
280.4
501.7
ALL using
Hybrid DFT B3PW91
R=
LnRe
F
R=
R=
LnRe
LnRe
R=
LnRe
F
F
R=
LnRe
R=
F
F
LnRe
R=
LnRe
F
F
R=
LnRe
F
F
R=
LnRe
F
F
R=
LnRe
F
F
R=
LnRe
F
F
F
R=
LnRe
F
Chem. Commun. 2003, 490-491
Compound

Theory Level
Bond (C-Y)
Energy
5
Re( -C5H5)(CO)2(H)(R)
R=
LnRe
Re-R
Re-H
280.8
503.6
Re-R
Re-H
281.0
504.8
Re-R
Re-H
257.4
495.0
Re-R
Re-H
304.7
512.4
Re-R
Re-H
304.0
514.7
Re-R
Re-H
283.0
504.4
Re-R
Re-H
306.7
514.7
ALL using
Hybrid DFT B3PW91
R=
LnRe
F
F
R=
LnRe
R=
R=
F
F
LnRe
F
LnRe
F
F
F
R=
LnRe
F
F
F
R=
LnRe
F
F
Chem. Commun. 2003, 490-491
Cr(CO)6
First Dissociation Enthalpy
M-CO
154
Mean Dissociation Enthalpy
M(CO)6
107
M-CO
170
M(CO)6
152
M-CO
192
M(CO)6
178
M-CO
174
M(CO)5
118
Mo(CO)6
W(CO)6
Fe(CO)5
Compound
Th(Cp*)3R

Bond Enthalpy Terms
Bond (C-Y)
Energy
R = Me
R = LnTh
Th-C
375
350
351
351
333
326
369
365
315
358
R = Me
R = Et
R = Bu
339
318
307
315
308
300
R=
302
295
335
331
R = Ph
372
328
R = Me
R = Et
R = Bu
349
330
316
326
320
309
R=
321
314
345
341
387
343
347
340
R=
LnTh
Me
R=
Me
Si Me
LnTh
R=
LnTh
Th(Cp*)2R2
LnTh
Me
R=
Me
Si Me
LnTh
t
Th(Cp*)2(O Bu)R
LnTh
Me
R=
Me
Si Me
LnTh
R = Ph
Th(Cp*)2[OCH(t- Bu)2]Bu
Compound
Th(Cp*)2(Cl)R

Bond Enthalpy Terms
Bond (C-Y)
Energy
R = Et
R = Ph
R = Bz
Th-C
313
374
285
Th(Cp*)2[(CH2)2CMe2]
274
Th(Cp*)2[(CH2)2SiMe2]
318
Th(Cp*)2(C4H6)
209
Th(Cp*)2[CH2(CMe)2CH2]
188
Th(Cp*)2(CHCH2CH2)2
368
Th(Cp*)2(OR)[C(O)H]
303
330
328
R=
345
396
351
402
342
317
293
300
244
276
287
307
303
ThLn
R=
ThLn
U(Cp*)2[OSi(t -Bu)Me2]R
U(Cp*)2R2
R=H
R = Me
U-C
R = Me
R = Bz
Me
R=
Si
Me
Me
LnU
U(Cp*)2(Cl)R
R = Me
R = Ph
R = Bz
312
358
263
288
314
306
U(Me3SiC5H4)3R
R = Me
R = Bu
185
152
161
145
168
164
149
223
363
192
185
R=
Me
Si
Me
Me
LnU
R = Bz
R = CHCH2
R = CCPh
Compound
TiR4
R=
Me
Me
Me
Me
Me
Si Me

Bond Enthalpy Terms
Bond (C-Y)
Energy
Ti-C
198
191
LnTi
R=
253
249
R = Bz
201
244
R = Me
R = Ph
298
332
274
288
343
299
LnTi
Ti(Cp)2R2
Me
R=
LnTi
R = LnTi
Me
342
298
R = LnTi
CF3
341
297
R = LnTi
OMe
350
306
278
237
280
293
291
5
5
R = ( -C5H4)Fe( -C5H5)
Ti(Cp)2Bz2
Ti(Cp)2(Cl)R
R = Me
R = Ph
Ti(Cp)2(Cl)Et
Ti(Cp*)2R2
150
281
280
257
236
249
242
310
306
263
306
Zr(Cp)2Me2
285
261
Zr(Cp)2Ph2
300
256
284
312
260
268
Zr(Cp*)2CH2(CHEt)2CH2
261
Zr(Cp*)2CH2CH2C6H4-o
282
276
252
ZrR4
R = Me
R = Ph
R=
Me
Me
Me
Me
Me
Si Me
Zr-C
L nZr
R=
LnZr
R = Bz
Zr(Cp*)2R2
R = Me
R = Ph
Zr(Cp*)2Me3
Zr(Cp*)(OC6F5)Me2
289
265
Zr(Cp*)(OC6F5)2Me
310
286
Compound

Bond Enthalpy Terms
Bond (C-Y)
Energy
Hf(Cp*)(CH2CMe3)4
266
259
346
306
274
346
282
267
326
350
294
326
306
270
Hf(Cp*)(OC6F5)Me2
300
276
Hf(Cp*)(OC6F5)2Me
309
285
Hf(Cp*)(C5Me4CH2CH2CH2)H
243
Hf(Cp*)(C5Me4CH2C6H4-o )H
320
Hf(Cp*)2(Me)C(O)Me
298
366
257
166
156
154
142
146
147
Mo(Cp)2(C2H4)
59
Mo(Cp)2(C2Ph2)
120
Mo(Cp)(CO)3H
273
282
203
185
147
154
282
179
175
195
197
160
347.3
136
311
221
311
197
Hf(Cp*)2R2
Hf-R
R=H
R = Me
R = Bu
Hf(Cp*)2H2
Hf(Cp*)(H)Ph
Hf(Cp*)Me3
Mo(Cp)2R2
Mo(Cp)(CO)3R
R=H
R = Me
R = Et
R = Bu
Mo-R
R=H
R = Me
R = Et
R = C3H5
R = Bz
W-Cl
W-R
WMe 6
W(Cp)2R2
R=H
R = Me
W(Cp)2(I)H
W(Cp)2(CO)3H
273
339
W(CO3)[P(c-C6H11)3]2(H2)
40
W(CO)5[C(OMe)Ph]
359
339
Compound
Mn(CO)5R

Bond Enthalpy Terms
Bond (C-Y)
Energy
R=H
R = Me
R = Ph
R = Bz
R = CH2F
Mn-Mn
Mn-R
R = CHF2
Mn(CO)5C(O)R
159
245
187, 192
207
129
139
245
163, 168
163
172
130
144
141
R = CF3
182, 203
156, 177
R = Me
R = Ph
R = CF3
R = Et
R = Pr
160, 182, 185

127, 131
176
181
175
Mn(CO)4(P(C6H4OMe-p )3(CH2C6H4OMe-p )
228, 250, 253

193, 197
222
242
236
105
Re-Re
Re-C
187
220
196
Fe(CO)4H2
Fe-H
272
244
Fe(CO)4(C2H4)
Fe-C
152
Re(CO)5Me
96
Fe(CO)(1,3-C4H6)2
178
Fe(CO)(1,3-c-C4H6)2
194
Fe(CO)3(1,3-C4H6)
200
Fe(CO)3(I)(C3H5)
170
Fe(CO)3(1,3,5,7-cyclooctatetraene)
179
Fe(CO)3(C2H4)2
113
Ru-C
Ru(2,3,7,8,12,13,17,18-octaethylporphyrinato anion)Et2
91
Compound

Bond Enthalpy Terms
Bond (C-Y)
Energy
Co(CO)4H
Co-C
227
227
Co3(CO)9(CCl)
114
Co3(CO)9(CBr)
135
Co(dimethylglyoxime) 2(R)CH(Me)Ph
R = pyridine
R = 4-methylpyridine
R = 4-aminopyridine
R = 4-cyanopyridine
R = imidazole
R = methylpyridine
R = PMe2Ph
113, 117, <90, <89

115
120, <97
106, <84
118, <96
91
100
R = PBu3
87
R = PEtPh2
81
R = PPh3
73
R = P(CH2CH2CN)3
85
Co(dimethylglyoxime) 2(R)Bz
R = PMe2Ph
128
171
R = PBu3
121
164
R = PEtPh2
113
156
R = PPh3
108
151
R = P(c-C6H11)3
96
139
Co(octaethylporphyrine)(R)Bz
R = PMe2Ph
114
157
R = PBu3
123
166
R = PEtPh2
110
153
R = PPh3
100
143
R = P(c-C6H11)3
124
167
Co(dimethylglyoxime) 2(R)CH(CH2X)COOMe
R = pyridine, X = H
R = 4-methylpyridine, X = H
R = 4-cyanopyridine, X = H
R = pyridine, X = COOMe
120
123
118
139
Co(dimethylglyoxime) 2(pyridine)R
R = Me
R = i -Pr
R = Bz
138
98
136
114
99
179
Compound

Bond Enthalpy Terms
Bond (C-Y)
Energy
Co(N,N' -bis(salicylidene)-o -phenylenediamine)(pyridine)R

R = Pr
Co-C
R = i -Pr
R = CH2CMe3
R = Bz
105
83
77
91
98
84
70
134
Co[11-hydroxyl-2,10-diethyl-3,9-dimethyl-1,4,8,11-tetraazaundeca-1,3,8,10-tetraen-1-olato](I)R
R = CH2CMe3
127
120
R = Bz
109
152
Co(dimethylglyoximeBF 2)2(H2O)Bz
Co(1,4,8,11-tetraazacyclotetradecane)2(H2O)Bz
[cobinamide]R
B12R
2+
R = i -Pr
R = CH2CMe3
R = Bz
R = Adenosine
R = i -Pr
R = i -Bu
R = CH2CMe3
R = Bz
R = CH2C5H9
B12Ado
Rh(Cp)(C2H4)2
Rh(octaethylporphyrine)R
R=H
R = C(O)H
R = CH(Bu)OH
99
142
98
141
110
126
105
144
111
119
148
79
104
90, 99
95
99
80
95
83, 92
138
112, 125, 131

Rh-C
<130
259
249
187
259
300
Rh(Cl)(B)[P(4-tolyl) 3]2H2
242
242
Rh(NC3H3C6H3CO)(Cl)(pyridine)C(Ph)(OMe)H
128
Ir(R)(CO)(PPh3)2H2 R = Cl
R = Br
R=I
247
253
258
272
Ir(Cl)(CO)(PPh3)2(R)H
R = Cl
R = Br
245
237
271
262
Ir(Cl)(CO)(PMePh2)2(Cl)H
266
291
Ir-C
270
Compound

Bond Enthalpy Terms
Bond (C-Y)
Energy
Ir(Cl)(CO)(PR3)2H2 R = Et
R = c-C6H11
Ir(R)(CO)(X)2H2
Ir-C
243
268
246
271
R = Cl, X = P(i -Pr)3
240
265
R = Cl, X = PBuPh2
242
267
R = Cl, X = PPh 3
251
276
R = Cl, X = P(c-C 6H11)3
240
265
R = Cl, X = PBz 4
249
274
R = Cl, X = P(p -tolyl) 3
246
271
R = Cl, X = P(OPh)3
244
269
R = Br, X = P(i -Pr)3
245
270
R = Br, X = PPh3
235
260
R = Br, X = P(c-C6H11)3
244
269
R = Br, X = P(OPh)3
238
263
R = I, X = P(i -Pr)3
227
252
R = I, X = PPh 3
229
254
R = I, X = P(c-C 6H11)3
256
281
R = I, X = P(OPh)3
224
249
Ir(Cl)2(CO)(R)2C(O)Me
R = PMe3
>237
R = PEt3
>241
Ir(Cp*)(PMe3)H2
Ir(Cp*)(PMe3)(R)H
Ir(Cp*)(PMe3)(H)R
310
310
R = Ph
R = c-C6H11
337
293
209
216
R = c-C5H9
215
R = c-C5H11
R = Ph
R = c-C6H11
244
321
218
277
225
R = 2,3-Me2Bu
240
237
R = CH2CMe2Et
<233
Ir(Cp*)(PMe3)Me2
243
219
Ir(Cp*)(PMe3)(Br)C2H3
326
288
Compound
Ir(R)(CO)(PPh3)2X

Bond Enthalpy Terms
Bond (C-Y)
Energy
R = F, X = C 2F4
Ir-X
79
R = F, X = C 4F6
99
R = Cl, X = C 2F4
67
R = Cl, X = C 4F6
96
R = Br, X = C2F4
41
R = Br, X = C4F6
79
R = I, X = C 2F4
57
R = I, X = C 4F6
82
Ni(cod)2
Ni-C
209
[Pd(C3H5)Cl]2
Pd-C
262
344
cis -Pd(Cl)2(cod)
Pd(I)(bipy)Me3
136
163
195
Pt(Cp)2Me2
195
trans -Pt(PEt3)2Ph2
159
cis -Pt(PEt3)2Me2
269
245
cis -Pt(PEt3)2(o -tolyl) 2
298
254
cis -Pt(PEt3)2(Cl)Me
251
227
cis -Pt(PEt3)2(Cl)(o -tolyl)
300
256
trans -Pt(PPh3)2(Cl)H
307
307
cis -Pt(PPh3)2(I)Me
242
218
trans -Pt(PEt3)2(Cl)Et
206
196
Pt(PPh 3)2(Cl)C(O)Ph
Pt(PMe2Ph)2(Cl)(Me)2C(O)Me
Pt(R)2CH2CH2CH2 R = Cl
R = Br
Pt(Cl)2(R)CH2CH2CH2
>232
306
120
122
>288
Pt(Cp)Me3
Pt-C
R = (py)2
R = (4-Mepy)2
R = bipy
Pt(Br)2(R)CH2CH2CH2
117
113
121
R = (py)2
1117
R = (4-Mepy)2
R = bipy
114
124
150
Pt(PPh3)2(dpcb)
217, 217
Compound
Pt(PPh3)2R

Bond Enthalpy Terms
Bond (C-Y)
Energy
R = C2H4
Pt-C
152
R = PhCHCH2
169
R = cis -C2H2Ph2
194
R = trans -C2H2Ph3
210
R = C2Ph2
181
R = C2(CN)4
R = pcbd
277
177
Pt(Cl)2(cod)
398
Pt(AsMe3)(X)(Me)R X = Cl, R = C 2F4
52
X = Br, R = C2F4
48
X = Cl, R = C 4F6
69
X = Br, R = C4F6
61
Pt(AsMe2Ph)(X)(Me)R
X = Cl, R = C 4F6
73
X = Br, R = C4F6
80
Compound
Sc-Me
Ti-Me
V-Me
Cr-Me
Mn-Me
Fe-Me
Co-Me
Ni-Me
Cu-Me
Zn-Me

Bond Enthalpy Terms
Bond (C-Y)
Energy
+
M -L
247
226
207
126
213
242
205
188
124
296
Y-Me
Ru-Me
Rh-Me
Pd-Me
Cd-Me
249
226
198
247
228
La-Me
Hg-Me
Lu-Me
231
285
190
Sc-CH2
M+-L
412
Ti-CH2
391
V-CH2
335
Cr-CH2
226
Mn-CH2
297
Fe-CH2
347
Co-CH2
326
Ni-CH2
314
Cu-CH2
268
Y-CH2
398
Nb-CH2
456
Rh-CH2
381
La-CH2
411
240
Lu-CH2
Compound
Ti-CH
V-CH
Cr-CH
Fe-CH
Co-CH

Theory Level
Bond (C-Y)
Energy
+
M -L
508
481
314
426
426
Nb-CH
Rh-CH
610
431
La-CH
524
V-C
Fe-C
Co-C
+
M -C
383
397
384
Nb-C
Rh-C
600
686
La-C
427
Sc-Me
Ti-Me
V-Me
Cr-Me
Mn-Me
Fe-Me
Co-Me
Ni-Me
Cu-Me
Zn-Me
M-Me
134
192
155
172
126
155
191
231
243
80
Compound

Theory Level
Bond (C-Y)
Energy
M+-Me
ScMe2
238
247
TiMe2
268
226
VMe2
203
207
FeMe2
>160
242
RuMe2
>176
226
CoMe2
255
205
RhMe2
>205
198
NiMe2
>214
188
PdMe2
>155
247
ZnMe2
115
296
CdMe2
109
228
HgMe2
96
285
263
188
182
M+-H 239
202
195
+
M -Me
Sc(H)Me
V(H)Me
Co(H)Me
ScL+
YL+
LaL+
L = C2H2
M-L+
L = C2H4
326
147, 167
L = C6H6
222
L = C2H4
>138
L = C3H4
>297
L = C3H6
>126
L = C4H6
>238
L = C2H4
>138
L = C3H4
>297
L = C3H6
>126
L = C4H6
>238
TiC6H6+
>205
Compound

Theory Level
Bond (C-Y)
Energy
VL+
L = C2
VC3H5
VC6H6
V(C6H6)2
NbCH2
527
L = C2H
497
L = C2H2
212
L = C2H3
367
L = C2H4
L = Et
209
234
427
260
239
2+
NbC6H6+
TaC6H6+
CrC6H6+
MoL+
FeC2H4
V-L+
L = C2H2
Nb-L+
819
Ta-L+
276
251<D< 301
Cr-L+
222
Mo-L
312
L = C2H4
137
L = 1,3-C4H6
245
L = C6H6
250
Fe-L+
Fe(C3H5)2+
142, 174
232
FeC3H6
155
FeC4H6
201
FeCp
Fe(c- C5H6)+
FeC6H4
FeC6H6
>364
213
318
230
RuC2H4
Ru-L+
>159
Co-L+
155, 192
CoC2H4
CoC3H6
201
CoC4H6
<218
Co(Cp)C4H6
>238
CoCp
Co(Cp)2+
Co(C6H6)
285
>201
271
Co(PhMe)
CoSiH2+
RhC2H4
356
513
RhC4H6+
RhC6H6
Rh-L+
>159
>236
276
Compound
NiC2H4

Proton Affinity
Bond (C-Y)
Energy
Ni-L+
Ni(C2H4)2
155
180
NiC3H5
243
NiC6H6
285
NiCF2
196
NiSiH2+
CuC6H6
271
+
Cu-L
209
Ni(Cp) -L
Ni(Cp )-L
L = PH3
L = MeOH
L = NO
L = Me2O
L = MeCHO
L = MeSH
L = EtOH
L = HCN
L = EtCHO
L = i -PrCHO
L = C2H3CHO
L = i -PrOH
L = t -BuCHO
L = Me2CO
L = i -BuOH
L = MeOAc
L = Et2O
190.4
190.8
192.0
196.2
196.7
197.1
198.7
199.2
201.3
205.4
206.3
207.1
207.5
212.1
212.5
213.0
213.0
-58.2
-84.1
-78
-49.8
-67.4
-68.6
-61.5
-109.2
-56.9
-49.0
-59.8
-43.9
-52.3
-32.6
-41.8
-41.4
-19.2
L = Me2S
213.8
-18.0
L = NH3
L = MeCN
L = MeNH2
218.8
222.6
231.0
0
-59.0
38.1
L = NMe3
236.0
80.8
L = Me2NH
237.7
64.9
L = AsMe3
L = MeNC
L = PMe3
239.3
241.0
241.0
36.4
-26.4
86.6
Mn(CO)5L
L=H
L = Me
L = CH2F
Homolytic
L = CHF2
L = CF3
L = Bz
L = Mn(CO)5
Mn+-L
172
137, 132
82
58
72, 93
153
166
Compound

Hydride/Electron Affinity
Bond (C-Y)
Energy
147
184 / 201
Mo(CO)6
172
184 / 192
W(CO) 6
194
184 / 192
Fe(CO)5
187
235 / 232
D [M(CO)-n -1-CHO]
Cr(CO)6
M-C
M = Sc
M = Ti
M=V
M-C
444
423
423
M=Y
M = Zr
M = Nb
M = Mo
M = Tc
M = Ru
M = Rh
M = Pd
418
561
568
482
564
648
580
436
M = La
M = Hf
M = Os
M = Ir
M = Pt
463
540
649
631
610
M-C2
M = Sc
M = Ti
M=V
M = Cr
M-C2
572
573
578
451
M=Y
M = Zr
M = Nb
M = Mo
M = Ru
M = Rh
638
581
656
500
519
433
M = La
M = Hf
659
674
pyCo(dimethylglyoxime) 2CH3
Co-C
33.1
pyCo(dimethylglyoxime) 2CH2C6H5
31.2
pyCo(dimethylglyoxime) 2CH(CH3)2
21.3
Toscano, P. J.; Seligson, A. L.; Curran, M. T.; Skrobutt, A. T.; Sonnenberger, D. C.Inorg. Chem. 1989, 28, 166-168
Compound

Hydride/Electron Affinity
Bond (C-Y)
Energy
CH3Co(Salen)H2O
Co-C
168
CH3Co(Salen)imidazole
152
CH3Co(Salen)benzimidazole
136
CH3Co(Salen)pyridine
127
C2H5Co(Salen)H2O
125
n -C4H9Co(Salen)H2O
107
n -C4H9Co(Salen)
108
i -C4H9Co(Salen)H2O
90
i -C3H7Co(Salen)H2O
81
i -C3H7Co(Saloph)pyridine
84
i -C3H7Co(DH)2pyridine
89
Li, G.; Zhang, F. F.; Chen, H.; Yin, H. F.; Chen, H. L.; Zhang, S. Y.J. Chem. Soc. Dalton Trans. 2002, 105-110
M CH3
M=Y
M = Zr
M = Nb
M = Mo
M = Tc
M = Ru
M = Rh
M = Pd
M=H
M-C
M=Y
M = Zr
M = Nb
M = Mo
M = Tc
M = Ru
M = Rh
M = Pd
M=H
M-C
M=Y
M = Zr
M = Nb
M = Mo
M = Tc
M = Ru
M = Rh
M = Pd
M=H
Siegbahn, P. E. M. J. Phys. Chem. 1995, 99 , 12723-12729
M-H
M-H
M-C
M-H
66.9
58.6
56.6
45.3
47.7
48.5
52.0
41.6
102.7
76.8
67.1
67.3
55.3
54.9
58.9
62.4
50.3
108.3
116.5
102.9
102.6
89.4
81.8
89.1
92.3
76.1
127.3
Compound
Me
M
Me
M
Me
M
Me

Theory Level
Bond (C-Y)
Energy
M=Y
M = Zr
M = Nb
M = Mo
M = Tc
M = Ru
M = Rh
M = Pd
M=H
M-C
M=Y
M = Zr
M = Nb
M = Mo
M = Tc
M = Ru
M = Rh
M = Pd
M=H
M-C
M=Y
M = Zr
M = Nb
M = Mo
M = Tc
M = Ru
M = Rh
M = Pd
M=H
M-C
M-H
M-H
M-H
61.6
54.7
53.3
42.2
44.9
46.5
50.3
40.9
99.8
62.9
55.9
54.6
43.6
46.1
47.7
51.8
42.0
100.6
58.3
51.7
51.0
40.6
43.2
45.7
50.3
41.1
98.2
Compound

Theory Level
Bond (C-Y)
Energy
R1 = SC7H7, R2 = NO2
R1
R2
R1 = SC7H7, R2 = Br
R1 = SC7H7, R2 = Cl
R1 = SC7H7, R2 = H
R1 = SC7H7, R2 = Me
R1 = SC7H7, R2 = OMe
R1 = S-TPCP, R 2 = NO2
R1 = S-TPCP, R 2 = Br
R1 = S-TPCP, R 2 = Cl
R1 = S-TPCP, R 2 = H
R1 = S-TPCP, R 2 = Me
R1 = S-TPCP, R 2 = OMe
C-R1 heterol.
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
12.95
26.95
-14.3
17.85
25.74
-18.1
18.38
23.96
-24.3
20.17
24.57
-21.9
20.75
23.68
-24.8
21.61
23.50
-24.8
14.44
44.16
-14.3
17.80
41.41
-17.3
18.09
39.40
-19.5
20.14
40.27
-18.6
20.75
39.38
-19.6
21.90
39.52
-19.6
Venimadhavan, S.; Amarnath, K.; Harvey, N.G.; Cheng, J.-P; Arnett, E.M.J.. Am. Chem. Soc., 1992, 114(1) , 221-229
Compound

Theory Level
Bond (C-Y)
Energy
R1 = S-9-PhXan, R2 = NO2
R1
R2
R1 = S-9-PhXan, R2 = Br
R1 = S-9-PhXan, R2 = Cl
R1 = S-9-PhXan, R2 = H
R1 = S-9-PhXan, R2 = Me
R1 = S-9-PhXan, R2 = OMe
R1 = S-Xan, R2 = NO2
R1 = S-Xan, R2 = Br
R1 = S-Xan, R2 = Cl
R1 = S-Xan, R2 = H
R1 = S-Xan, R2 = Me
R1 = S-Xan, R2 = OMe
R1 = SCPh3, R2 = NO2
R1 = SCPh3, R2 = Br
R1 = SCPh3, R2 = Cl
R1 = SCPh3, R2 = H
R1 = SCPh3, R2 = H
R1 = SCPh3, R2 = Me
R1 = SCPh3, R2 = OMe
C-R1 heterol.
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
heterolysis
homolysis
radical cation
radical cation
radical cation
radical cation
radical cation
radical cation
radical cation
radical cation
18.33
26.1
-10.4
23.05
24.71
-13.1
24.36
23.71
-14.6
26.11
24.29
-13.6
26.94
23.64
-14.8
27.85
23.51
-15.0
21.66
29.32
-6.27
24.70
26.25
-9.45
25.87
25.11
-10.4
26.43
24.49
-11.1
27.16
23.75
-11.8
27.67
23.22
-12.3
-11.0
-14.7
-15.0
-14.5
-15.3
-15.3
-16.0
Compound

Theory Level
Bond (C-Y)
Energy
C-OO
Me
R = OO
Me
R
dissociated radical
as trans or cis
trans, cis
19.6, 23.1 B3P86-HLM
Me
20.5, 21.3 B3P86-HLM

Me
R
Me
Me
7.9, 7.4
B3P86-HLM
8.4,
B3P86-HLM
R
Me
Me
R
R
14.2, 77.4 B3P86-HLM
Me
Me
Me
14.6, 77.7 B3P86-HLM
Me
Me
Me
4.2
B3P86-HLM
6.0
B3P86-HLM
R
R
Me
Me
Me
9.8, 11.2 B3P86-HLM
Me
R
R
Me
11.7, 12.9 B3P86-HLM
Me
Pratt, D. A.; Mills, J. H.; Porter, N. A. J. Am. Chem. Soc. 2003, 125 , 5801-5810
HO
CH3
MeO
CH3
H2 N
CH3
O 2N
CH3
C-O
C-N
92.1
83.2
85.2
61.0
Compound
HO

Theory Level
Bond (C-Y)
Energy
C-O
92.1
94.0
CH3
CH3
HO
Me
95.5
Me
HO
Me
Me
Me
95.8
HO
HO
80.1
OH
112.4
OH
82.6
O
H
109.5
OH
O
Me
109.9
OH

MeO
CH3
CH3
C-OMe
MeO
85
Me
Me
85.8
MeO
Me
83.2
Me
Me
84
MeO
101
OMe
MeO
38
OMe
O
99.6
OMe
100
Me
OMe

H2N
C-NH2
CH 3
85.2
84.8
Me
86.0
Me
Me
85.7
CH3
H 2N
Me
H2N
Me
H2N
NH2
NH2
104.2
71.7
O
Me
NH2
99.1
Compound
O2 N

Theory Level
Bond (C-Y)
Energy
C-NO2
CH3
61.0
CH3
O 2N
61.6
Me
Me
O2N
Me
62.9
Me
Me
62.8
O2N
72.5
NO2
NO2
50.5
C-O
106.3
H 2C
H3 C
H3C
90.5
C O
174
92.1
H
H
154
H
H
O
178.8
28
109.3
100
H O
H
H O
H
O
Me
Me
Me
Me
Me
Me
74
38
Compound

Theory Level
Bond (C-Y)
Energy
C-O
59.3
DFT I
65.2
DFT II
63.5
DFT III
65.3
Experimental
CH3
O
CH3
H2N
H2N
NH2
52.8; 52.5
DFT II
-9.2
-9.5
-8.9
DFT I
DFT II
DFT III
-9.3
DFT II
-1.4
DFT II
-6.0
-6.1
-5.5
DFT I
DFT II
DFT III
-6.1
DFT II
-0.5
DFT II
3.7
3.0
2.8
DFT I
DFT II
DFT III
3.0
DFT II
-0.1
DFT II
5.2
4.6
4.5
DFT I
DFT II
DFT III
4.7
DFT II
-0.9
DFT II
-4.5
-4.7
DFT II
DFT III
CH3
MeO
MeO
OMe
O
CH3
F 3C
F 3C
CF3
O
CH3
O2N
O2N
NO2
O
O
CH3
HO
Pratt, D. A.; de Heer, M. I.; Mulder, P.; Ingold, K. U.J. Am. Chem. Soc. 2001, 123 , 5518-5526
Compound

Theory Level
Bond (C-Y)
Energy
62.6
Experimental
CH3
62.3
Experimental
CH3
61.2
Experimental
62.2
Experimental
67.5
Experimental
58.1
Experimental
CH3
HO
C-O
O
O
HO
OMe
O
CH3
MeO
O
CH3
F3C
OH
CH3
O
Pratt, D. A.; de Heer, M. I.; Mulder, P.; Ingold, K. U.J. Am. Chem. Soc. 2001, 123 , 5518-5526
H3C
H3C
H3C
C-N
C-O
C-S
(kJ/mol)
356
385.7
307.8
H3 C O
80.9
66.3
68.8
DFT-AM1
Experimental
Corrected
H3C
65.1
57.0
55.3
DFT-AM1
Experimental
Corrected
83.2
67.0
70.7
DFT-AM1
Experimental
Corrected
72.6
66.8
61.7
DFT-AM1
Experimental
Corrected
56.3
49.6
47.4
DFT-AM1
Experimental
Corrected
63.7
52.9
54.1
DFT-AM1
Experimental
Corrected
Me
Me
Me
C-O
H3C
H3 C
SMe
O
S
Me
O
S
Me
C-S
Compound
H3C

Theory Level
Bond (C-Y)
Energy
C-N
89.4
84.9
84.9
DFT-AM1
Experimental
Corrected
74.0
71.9
70.3
DFT-AM1
Experimental
Corrected
Me
NH
73.3
67.7
69.6
DFT-AM1
Experimental
Corrected
CH3
56.4
52.5
53.6
DFT-AM1
Experimental
Corrected
52.5
50.0
49.9
DFT-AM1
Experimental
Corrected
48.4
47.5
46.0
DFT-AM1
Experimental
Corrected
46.9
43.5
44.6
DFT-AM1
Experimental
Corrected
63.4
62.0
60.2
DFT-AM1
Experimental
Corrected
54.8
51.5
52.1
DFT-AM1
Experimental
Corrected
51.7
50.5
49.1
DFT-AM1
Experimental
Corrected
78.8
74.3
Experimental
B3LYP/6-31G(d), 298K
76.0
73.4
Experimental
B3LYP/6-31G(d), 298K
NH2
NH2
MeN
Me
EtN
Me
Me
N
N
Me
Me
Me
Me
Me
N
N
Me
Me
Me
NO2
Me
NO
NO
F
C-O
O
Compound

Theory Level
Bond (C-Y)
Energy
c-C6 H11
C-H
C-OO
97
24
(PAC)
c-C6H7
C-H
C-OO
77
12, 13
(PAC)
c-C4H 8N
C-H
C-OO
88.2, (87)
27.8, (10)
DFT, (Expt)
DFT, (Expt)
N(Et)2CHCH 3
C-H
C-OO
89.9, 89
30.2 (25,24)
DFT, (Expt)
DFT, (Expt)
C4 H7 O
C-H
C-OO
90.7, 91.6, (92)

32.4, (32)
DFT, (Expt)
DFT, (Expt)
C4 H7O2
C-H
C-OO
94.6, (96)
31.6, (34)
DFT, (Expt)
DFT, (Expt)
C-H
OO
C-OO
H3C
H 3C
C-H
C2H5
OO
C-OO
C3 H7
C3 H7
OO
C2 H5
C-H
Me
C-OO
C-H
Me
H
Me
C-OO
Me
OO
Me
C-H
Me
H
Me
C-OO
Me
OO
c-C3H5
c-C3H5
OO
C-H
C-OO
105.0, 105.7
105
31.4, 31.1
33
DFT
Experimental
DFT
Experimental
100.3, 101.0
101
32.4
35
DFT
Experimental
DFT
Experimental
100.9, 101.6
101
33.0
DFT
Experimental
DFT
96.4, 97.1
98
32.3
37
DFT
Experimental
DFT
Experimental
93.2, 94.0
96
31.4
37
DFT
Experimental
DFT
Experimental
106.4, 107.2
39.5
DFT
DFT
Compound

Theory Level
Bond (C-Y)
Energy
C-H
97.3, 98.0
DFT
OO
C-OO
34.2
DFT
c-C6H11
C-H
96.9, 97.6
97
DFT
Experimental
c-C6H11
OO
C-OO
32.7
24
DFT
Experimental
C-H
109.3
111
DFT
Experimental
C-OO
45.2
DFT
C-H
105.7
DFT
C-OO
44.1
DFT
C-H
110.8
113
DFT
Experimental
C-OO
46.2
DFT
C-H
85.0, 85.9
88
DFT
Experimental
C-OO
14.8
18
DFT
Experimental
C-H
80.2, 81.5
84
DFT
Experimental
C-OO
14.9
DFT
c-C4H7
c-C4H7
C2H3
C2 H3
OO
Me
H
Me
OO
OO
OO
Me
H
Me
OO
c-C6H7
C-H
71.4, 72.3
77
DFT
Experimental
c-C6H7
OO
C-OO
5.9
12
DFT
Experimental
C-H
87.8, 88.6
90
DFT
Experimental
C-OO
18.2
22
DFT
Experimental
OO
Compound

Theory Level
Bond (C-Y)
Energy
H
Me
OO
C-H
84.8, 85.7
87
DFT
Experimental
C-OO
18.9
DFT
Me
Cl3C
C-H
92.1
96
DFT
Experimental
Cl3C
OO
C-OO
17.2
20
DFT
Experimental
C-OH
O
H
OH
O
Me
108.7
G3
109.2
G3
108.9
G3
109.9
CBS-4M
OH
O
OH
O
OH
C-OH
O
H2 N
109.2
OH
O
HO
109.7
OH
O
H3 C
109.8
OH
O
H
OH
O
F
109.9
110.1
OH
O
HOOC
OH
O
F 3C
110.4
110.6
OH
O
NC
OH
110.7
O
O2N
OH
110.9
Compound

Theory Level
Bond (C-Y)
Energy
110.2
110.5
110.3
G2
G2MP2
G2MS
108.8
109.3
109.1
G2
G2MP2
G2MS
CF3
109.9
109.8
G2MP2
G2MS
CF3
108.1
108.1
G2MP2
G2MS
80.8
81.4
83.2
75.3
G2
G2MP2
G2MS
Experimental
99.8
Experimental
73.2
74.1
74.7
73.6
G2
G2MP2
G2MS
Experimental
78.4
Experimental
99.1
G3
98.5
G3
98.9
G3
99.8
CBS-4M
CF3
C-O
F3C O
Me
F3C
F
F3C
O
F
F3C
O
Me
H3C
C-N
Me
CF3
F3C
N
CF3
H3C
SMe
F3C
C-S
CF3
C-N
O
NH2
H
O
NH2
Me
O
NH2
O
NH2
Compound

Theory Level
Bond (C-Y)
Energy
O
C-SMe
77.5
H2 N
SMe
O
77.9
HO
SMe
78.1
H3 C
SMe
O
78.3
H
SMe
O
F
78.4
SMe
O
78.9
HOOC
SMe
O
F 3C
79.1
SMe
O
NC
79.3
SMe
O
79.5
O2N
SMe
O
H2N
NH2
C-NH2
O
HO
98.2
99.1
NH2
O
H3C
NH2
O
H
99.4
99.8
NH2
O
F
NH2
99.7
O
HOOC
NH2
100.7
O
F 3C
NH2
100.8
O
NC
NH2
101.0
O
O 2N
NH2
101.3
ALL ab-initio
Compound
OO
OO
OO

Theory Level
Bond (C-Y)
Energy
C-O
22.2
21.8
B3P86-MLM
Experimental
20.6
21.2
19.8
19.7
19.0
18.4
B3P86-LLM
B3P86-MLM
B3P86-MLM
G3MP2
G3
Experimental
15.3
15.0
14.0
15.1
13.9
13.4
B3P86-LLM
B3P86-MLM
B3P86-MLM
G3MP2
G3
Experimental
Pratt, D. A.; Mills, J. H.; Porter, N. A. J. Am. Chem. Soc. 2003, 125 , 5801-5810 Reference includes radical stabilization energies
Compound

Theory Level
Bond (C-Y)
Energy
OtBu
O-O
Cl
Cl
I-I
Cl-Cl
BuO
172.5
172.3
151.3
243.36
H
O-H
87.2
79.3
83.1
Experimental
B3LYP/6-31G(d), 298K
B3LYP/6-311++G(d,p), 298K
O H
O-H
84.3
74.8
79.8
Experimental
B3LYP/6-31G(d), 298K
B3LYP/6-311++G(d,p), 298K
HOH
114.2
115.1
118.4
119.0
B3LYP 6-311G(d,p)
(RO)B3LYP 6-311++G(3df,2p)
Experimental
86.2
88.0
86.3
88.3
88.3
94
96
87.4
87
84
87
87
(Solvent)
isooctane
CCl4
benzene
acetonitrile
ethyl acetate
DMSO
NEt3
solution average
gas phase
benzene
benzene
various
O-H
Compound
Ru
Ru
Rh
Rh
Pd
Pd
Sn
Sn
Ru

Theory Level (DFT)
Bond (C-Y)
Energy
M-M
40.6
37.1
46.6
46.1
33.0
29.7
32.4
56.8, 32.3, 18.08, 26.7
GGA-BP86
GGA-BPD91
GGA-PD91
Experimental
GGA-BP86
GGA-BPD91
GGA-PD91
Experimental
33.9
25.5
31.8
25.0
GGA-BP86
GGA-BPD91
GGA-PD91
Experimental
60.5
58.9
61.7
46.9, 44.9
GGA-BP86
GGA-BPD91
GGA-PD91
Experimental
Sn
61.1
58.2
64.0
GGA-BP86
GGA-BPD91
GGA-PD91
Rh
Sn
57.6
54.6
61.0
GGA-BP86
GGA-BPD91
GGA-PD91
Pd
Sn
66.4
63.2
65.5
GGA-BP86
GGA-BPD91
GGA-PD91
Xavier, E. S.; Duarte, H. A.J. Quant. Chem. 2003, 95(2) , 164-176
Compound
M(BMe)4

Theory (DFT)
Bond (C-Y)
Energy
M = Ni
M-BMe
87.2
87.9
72.5
70.2
85.5
83.4
BP86/II
BP86/TZP
BP86/II
BP86/TZP
BP86/II
BP86/TZP
M-AlMe
59.4
62.9
50.4
51.4
60.4
60.6
BP86/II
BP86/TZP
BP86/II
BP86/TZP
BP86/II
BP86/TZP
M-GaMe
47.5
51.5
BP86/II
BP86/TZP
Experimental
BP86/II
BP86/TZP
BP86/II
BP86/TZP
Experimental
M = Pd
M = Pt
M(AlMe)4
M = Ni
M = Pd
M = Pt
M(GaMe)4
M = Ni
M = Pd
38.0
39.9
46.4
48.0
M = Pt
M(InMe)4
M = Ni
M-InMe
M = Pd
M = Pt
M(TlMe)4
M = Ni
M = Pd
M = Pt
Doerr, M.; Frenking, G. Z. Anorg. Allg. Chem. 2002, 628 , 843-850
M-TlMe
48.2
44.9
40.7
35.0
48.6
41.5
BP86/II
BP86/TZP
Experimental
BP86/II
BP86/TZP
BP86/II
BP86/TZP
35.6
34.0
25.2
24.2
29.4
27.8
BP86/II
BP86/TZP
BP86/II
BP86/TZP
BP86/II
BP86/TZP
Reference includes bond distances
Compound

Solvent
Bond (C-Y)
Energy
Sn-H
78
isooctane
Si-H
96
isooctane
91
isooctane
84
isooctane
87
benzene
86
benzene
88
benzene
86
benzene
85
benzene
85
benzene
87
benzene
Si-H
90
benzene
N-H
91
benzene
Cl
S-Cl
70
benzene
71
benzene
90
benzene
87
benzene
Me
Sn H
Si H
Me
Me
Me Si Si H
Me
Me
Me
Me Si
Me
Si H
Me
Ge-H
Me Ge H
Me
Et
Et Ge H
Et
Bu
Bu Ge H
Bu
Ph
H Ge H
H
Ph
Ph Ge H
H
Ph
Ph Ge H
Ph
MeS
MeS Si
MeS
Me
S
Si H
Me
3
Me
N
Me
O
Me
S
O
O
Ph
S
O
Cl
H
N
N-H
Compound

Theory Level
Bond (C-Y)
Energy
O-H
87.8
88
85
H O
Me
Et
Me
Me
Me
84
O
O
88.144
H
O
Me
89.4
O
H
94
H
O
112
H
O
96
Me
112
O
O
O
H
111
Ph
H
H3C O
H3C
S
H
S
H
O
Me
Me
H
104.6
S-H
87.4
C-H
94
O-H
104.7
105.7
Me
Me
Me
Me
Ph
O2 N
H
O
106.3
H
OMe
N-O
90
42
Compound

Theory Level
Bond (C-Y)
Energy
H-Y
H H
H
NH2
OH
H O
H O
115.2
91.2
84.1
49.5
79.1
H O
H
SH
NO
104.206
107.6
118.82
101.76
110.21
N O
H O
O
101.7
N O
H O
H
SiH3
91.7
83
H GeH3
O-H
H
CH 2
H 3C
30.2
104.6
H O
H
112
O
H O
Me
Me
Me
85
O
O
Me
Me
Me
Me
Me
Me
O-O
O
O
47
65
Compound

Theory Level
Bond (C-Y)
Energy
Th(Cp*)2(OR)H
Th-O
Th-OR
R=
518.8
389
389
384
384
OThL n
R=
OThLn
[Th(Cp*)2H2]2
Th-H
Ti-Cl4
Ti-Cl
Zr(Cp*)2R2
Mn(CO)5R
R=H
R=H
Fe(CO)4H2
Zr-Cl
Zr-H
390
430.5
339
491.4
339
Hf-Cl
497.6
Mn-Mn
159
Mn-H
Re-Re
Fe-H
245
272
245
187
244
Compound
Sc-H
Ti-H
V-H
Cr-H
Mn-H
Fe-H
Co-H
Ni-H
Cu-H
Zn-H

Bond (C-Y)
Energy
M-H
202
197
172
172
126
191
190
243
255
86
Mo-H
Ru-H
Rh-H
Pd-H
Ag-H
Cd-H
208
234
247
234
215
69.0
Au-H
Pt-H
Yb-H
292
352
159
Sc-H
Ti-H
V-H
Cr-H
Mn-H
Fe-H
Co-H
Ni-H
Cu-H
Zn-H
+
M -H
239
227
202
136
203
208
195
166
92
231
Y-H
Zr-H
Nb-H
Mo-H
Ru-H
Rh-H
Pd-H
Ag-H
261
230
226
176
172
151
197
67
La-H
Lu-H
U-H
243
204
208
Compound
Sc-H
Ti-H
V-H
Cr-H
Mn-H
Fe-H
Co-H
Ni-H
Cu-H
Zn-H

Bond (C-Y)
Energy
M-H+
918
881
864
795
797
761
749
741
658
637
Y-H
Zr-H
Nb-H
Mo-H
Ru-H
Rh-H
Pd-H
Ag-H
973
906
902
803
783
736
704
648
La-H
Lu-H
U-H
1017
992
995
Cr-H
Mn-H
Fe-H
Co-H
Ni-H
M -H
162
>210
265
191
177
M-H-
153
137
208
182
217
Cr-H
Mn-H
Fe-H
Co-H
Ni-H
Compound
Sc-H
Ti-H
V-H
Cr-H
Mn-H
Fe-H
Co-H
Ni-H
Cu-H
Zn-H

Bond (C-Y)
Energy
M+-H-
762
782
750
752
771
878
876
907
928
919
Mo-H
Ru-H
Rh-H
Pd-H
Ag-H
Cd-H
820
863
902
966
874
864
Au-H
Pt-H
Yb-H
1109
1110
689
Sc-H
Ti-H
V-H
Cr-H
Mn-H
Fe-H
Co-H
Ni-H
Cu-H
Zn-H
M -H
1496
1501
1433
1419
>1438
1488
1438
1443
1448
>1398
Mo-H
Ru-H
Rh-H
Pd-H
Ag-H
Cd-H
1448
1445
1449
1492
1402
>1380
Au-H
Pt-H
1381
1458
Cd-H
Au-H
Hg-H
49
>113
6
Compound
ScH2

Bond (C-Y)
Energy
M+-H
244
239
YH2
272
261
LaH2
266
243
LuH2
207
204
CoH2
209
195
263
188
182
M+-H 239
202
195
190.4
190.8
192.0
196.2
196.7
197.1
198.7
199.2
201.3
205.4
206.3
207.1
207.5
212.1
212.5
213.0
213.0
Proton Affinity (kJ/mol)

-58.2
-84.1
-78
-49.8
-67.4
-68.6
-61.5
-109.2
-56.9
-49.0
-59.8
-43.9
-52.3
-32.6
-41.8
-41.4
-19.2
L = Me2S
213.8
-18.0
L = NH3
L = MeCN
L = MeNH2
218.8
222.6
231.0
0
-59.0
38.1
Sc(H)Me
V(H)Me
Co(H)Me
+
M -Me
+
Ni(Cp) -L
L = PH3
L = MeOH
L = NO
L = Me2O
L = MeCHO
L = MeSH
L = EtOH
L = HCN
L = EtCHO
L = i -PrCHO
L = C2H3CHO
L = i -PrOH
L = t -BuCHO
L = Me2CO
L = i -BuOH
L = MeOAc
L = Et2O
M(Cp+)-L
L = NMe3
236.0
80.8
L = Me2NH
237.7
64.9
L = AsMe3
L = MeNC
L = PMe3
239.3
241.0
241.0
36.4
-26.4
86.6
Compound

Electron Affinity
Bond (C-Y)
Energy
Mn-Mn
Mn-H
R+-H
159
245
R = V(CO)6
R -H
220
R = Cr(CO)6
230
R = Cr(CO)2(Cp)NO
207
R = Cr(CO)3(Cp)Me
244
R = Cr(CO)3Bz
221
R = Mo(CO)6
260
R = W(CO) 6
257
R = Mn(CO)5H
349
R = Mn(CO)5Me
267
R = Cr(CO)3(MeC5H4)
283
R = Mn(CO)10
204
R = Re(CO)5Me
294
R = Re2(CO)10
246
R = MnRe(CO)10
<267
R = Fe(CO)5
299
R = Fe(Cp)2
215, 198, 202
R = Fe(CO)2(Cp)Me
210
R = Ru(Cp)2
271
R = Co(CO)2(Cp)
245
R = Rh(CO)2(Cp)
287
R = Ni(CO)4
248
R = Ni(Cp)2
R = Ni(Cp)NO
215
315
1331
245
232
Co(CO)4H
1334
1314
227
Fe(CO)4H
1335
232
Mn(CO)5H
LnM--H+
Fe(CO)4H2
pyCo(dimethylglyoxime) 2I
Co-I
(kcal/mol)
34.6
Toscano, P. J.; Seligson, A. L.; Curran, M. T.; Skrobutt, A. T.; Sonnenberger, D. C.Inorg. Chem. 1989, 28, 166-168
Compound
M-O

Theory Level
Bond (C-Y)
Energy
M = Sc
M = Ti
M=V
M = Cr
M = Mn
M = Fe
M = Co
M = Ni
M = Cu
M = Zn
M-O
681
672
625
429
403
390
384
381
270
271
M=Y
M = Zr
M = Nb
M = Mo
M = Tc
M = Ru
M = Rh
M = Pd
M = Ag
M = Cd
719
776
769
560
548
528
405
381
221
236
M = La
M = Hf
M = Ta
M=W
M = Re
M = Os
M = Ir
M = Pt
M = Au
M = Hg
801
801
799
672
627
598
414
391
223
213
H2O
H2CO
MeOH
MeC(O)H
EtOH
(Resultant Radical)
OH
HCO
EtO
MeCHOH
EtC(O)H
MeC(O)CH3
PrOH
i -PrOH
PrC(O)H
BuOH
s -BuOH
i -BuOH
t -BuOH
O-H
499
463.5
372
438
359
436
389
366
411
432
438
366
430
443
440
440
423.4
451.2
426.6
451.2
401.7
426.6
410.8
451.2
451.2
426.6
451.2
451.2
451.2
451.2
Compound
Me

Theory Level
Bond (C-Y)
Energy
O-O
27.2
37.6
DFT-AM1
Experimental
Me
35.0
46.3
DFT-AM1
Experimental
Me
31.0
37.9
DFT-AM1
Experimental
Me
29.7
37.7
DFT-AM1
Experimental
Me
Me
Me
24.3
38.0
DFT-AM1
Experimental
21.1
35.5
DFT-AM1
Experimental
21.6
30.4
DFT-AM1
Experimental
66.5
70.8
DFT-AM1
Experimental
O
O Me
H O
O
Me
Me
Me
O
O
Me
O
Me
O
Me
Me
Me
Me
O
O
F3 C
F3C
F3 C
O
O
CF3
CF3
CF3
O
O
Me
Me
O
O
N-N
H2N
NH2
HN
Me
NH2
63.6
64.8
DFT-AM1
Experimental
N NH2
59.5
62.7
DFT-AM1
Experimental
Me
Me
Compound

Theory Level
Bond (C-Y)
Energy
H-H
H H
79.5
95.8
106.4
104.2
HF
MP2
B3LYP
Experimental
136.25
103.15
87.54
71.32
H F
H Cl
H Br
H
M=Y
M = Zr
M = Nb
M = Mo
M = Tc
M = Ru
M = Rh
M = Pd
M=H
M H
M-H
H-H
70.0
58.8
63.0
54.0
52.1
62.4
68.2
53.4
104.8
4-methoxythiophenol
R
R = OMe
S-H heterol.
heterolysis
31.92
27.85
27.67
21.90
21.61
23.80
29.24
11.47
30.24
homolysis
77.3
23.51
23.22
39.52
23.56
11.65
27.16
16.77
20.85
SH
9-Phenylxanthylium (rxn)
xanthylium (rxn)
triphenylcyclopropenylium
triopylium (rxn)
perinaphthenium (rxn)
4,4'-dimethoxydiphenylmethyl
triphenylpyrylium (rxn)
9,9-dimethyl-10-phenyl9,10-dihydroanthracenium
xanthylium (rxn)
triopylium (rxn)
Compound
4-nitrothiophenol
R

Theory Level
Bond (C-Y)
Energy
R = NO2
S-H heterol.
heterolysis
23.34
18.33
21.66
14.44
12.95
16.19
19.09
22.60
homolysis
81.6
26.10
29.32
44.16
26.95
27.42
24.32
SH
4-bromothiophenol R = Br
heterolysis
homolysis
4-chlorothiophenol R = Cl
heterolysis
homolysis
26.87
23.05
24.70
17.80
17.85
18.50
23.50
24.75
80.2
24.71
26.25
41.41
25.74
12.34
27.42
21.36
27.53
24.36
25.87
13.09
18.38
20.37
23.88
25.32
78.4
23.71
25.11
39.40
23.96
11.91
25.49
19.62
xanthylium (rxn)
triopylium (rxn)
xanthylium (rxn)
triopylium (rxn)
xanthylium (rxn)
triopylium (rxn)
triopylium (rxn)
xanthylium (rxn)
triopylium (rxn)
xanthylium (rxn)
triopylium (rxn)
xanthylium (rxn)
triopylium (rxn)
Compound
thiophenol
R

Theory Level
Bond (C-Y)
Energy
R=H
S-H heterol.
heterolysis
29.25
26.11
26.43
20.14
20.37
22.42
26.47
9.05
27.08
homolysis
78.5
24.29
24.49
40.27
24.57
12.78
26.91
16.87
20.21
SH
4-methylthiophenol R = Me
heterolysis
homolysis
29.90
26.94
27.16
20.75
20.75
22.98
27.90
10.45
28.85
77.8
23.64
23.75
39.38
39.52
11.87
26.86
16.79
20.50
xanthylium (rxn)
triopylium (rxn)
xanthylium (rxn)
triopylium (rxn)
xanthylium (rxn)
triopylium (rxn)
xanthylium (rxn)
triopylium (rxn)
Compound

Theory Level
Bond (C-Y)
Energy
110.6
110.0
DFT-AM1
Experimental
48.5
49.5
DFT-AM1
Experimental
73.5
75.7
DFT-AM1
Experimental
N3
89.7
87.0
DFT-AM1
Experimental
HO
116.8
119.0
DFT-AM1
Experimental
102.7
104.4
DFT-AM1
Experimental
85.9
88.0
DFT-AM1
Experimental
89.5
87.2
DFT-AM1
Experimental
110.0
110.0
DFT-AM1
Experimental
Me
107.0
106.0
DFT-AM1
Experimental
76.8
78.3
DFT-AM1
Experimental
100.0
101.2
DFT-AM1
Experimental
90.9
90.5
DFT-AM1
Experimental
87.8
88.0
DFT-AM1
Experimental
H2N
ON
F 2N
MeO
N-H
O-H
H O
O
H
O
O
O
O
NO
NO 2
HS
MeS
S-H

8 - Bond Dissociation Enthalpy Data

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8 - Bond Dissociation Enthalpy Data

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The Lectka Group at Johns Hopkins

Bond Dissociation Enthalpy Data

Bond Dissociation Enthalpy (kcal/mol)

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Bond Dissociation Enthalpy (kcal/mol)

Polycyclic Aromatic Hydrocarbon Borders

Bond Dissociation Enthalpy (kcal/mol)

Olleta, A. C.; Lane, S. I.Phys. Chem. Chem. Phys. 2001, 3 , 811-818

Bond Dissociation Enthalpy (kcal/mol)

Jursic, B. S. J. Chem. Soc. Perkin Trans. 1999, 2 , 369-372

Bond Dissociation Enthalpy (kcal/mol)

Seetula, J. A. J. Chem. Soc Faraday Trans. 1998, 94 , 891-898

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Bond Dissociation Enthalpy (kcal/mol)

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Bond Dissociation Enthalpy (kcal/mol)

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Bond Dissociation Enthalpy (kcal/mol)

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Bond Dissociation Enthalpy (kcal/mol)

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Bond Dissociation Enthalpy (kcal/mol)

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255

Bond Dissociation Enthalpy (kcal/mol)

Zavitsas, A. A. J. Phys. Chem. A 2003, 107, 897-898

Reference includes bond distances in Angstroms

Bond Dissociation Enthalpy (kcal/mol)

Zavitsas, A. A. J. Phys. Chem. A 2003, 107, 897-898

Bond Dissociation Enthalpy (kcal/mol)

Zavitsas, A. A. J. Phys. Chem. A 2003, 107, 897-898

Bond Dissociation Enthalpy (kcal/mol)

Bond Dissociation Enthalpy (kcal/mol)

Bond Dissociation Enthalpy (kcal/mol)

Bond Dissociation Enthalpy (kcal/mol)

Kitagawa, T.; Takeuchi, K.J. Phys. Org. Chem. 1998, 11 , 157-170

Kitagawa, T.; Takeuchi, K.J. Phys. Org. Chem. 1998, 11 , 157-170

Kitagawa, T.; Takeuchi, K.J. Phys. Org. Chem. 1998, 11 , 157-170

Bond Dissociation Enthalpy (kcal/mol)

Bond Dissociation Enthalpy (kcal/mol)

Bond Dissociation Enthalpy (kcal/mol)

Chem. Eur. J. 2003, 9(4) , 871-880

Bond Dissociation Enthalpy (kcal/mol)

Bond Dissociation Enthalpy (kcal/mol)

Bond Dissociation Enthalpy (kcal/mol)

All Calculated with DFT

Bond Dissociation Enthalpy (kcal/mol)

Bond Dissociation Enthalpy (kcal/mol)

Reed, D. R.; Kass, S. R. J. Mass Spectrom . 2000, 35 , 534539

Bond Dissociation Enthalpy (kcal/mol)

J . Org. Chem . 1995, 60 , 6348-6352

Reference includes radical anion dissociation energies

Bond Dissociation Enthalpy (kcal/mol)

Zhang, X.-M.J. Org. Chem. 1998, 63, 1872-1877

Bond Dissociation Enthalpy (kcal/mol)

Zhang, X.-M.J. Org. Chem. 1998, 63 , 1872-1877

Bond Dissociation Enthalpy (kcal/mol)

Zhang, X.-M.J. Org. Chem. 1998, 63 , 1872-1877

Bond Dissociation Enthalpy (kcal/mol)