Table 2

Experimentally measured energy differences in activation energies for aliphatic P450 oxidation reactions

Compound	Reference	Regioselectivity Positions	Measured Δ kcal/mol^2-a	Predicted Δ kcal/mol^2-b
Ethylbenzene	White et al., 1996	Primary/benzylic	−4.39	−4.58
α-Chloro-p-xylene	Higgins et al., 2001	Benzylic/CI-methyl benzylic	−0.74	−1.31
2-Methylanisole	Higgins et al., 2001	Benzylic/O-demethylation	0.40	2.25
4-Methylanisole	Higgins et al., 2001	Benzylic/O-demethylation	0.72	2.21
1,3-Diphenylpropane	Hjelmeland et al., 1977	Benzylic/secondary	1.28	2.44
Hexane	Morohashi et al., 1983	1/2 Hexanol	−1.85	−2.15
Octane	Jones et al., 1990	1/2 Octanol	−2.14	−2.14
1-Phenyl-3-(4-fluorophenyl)propane	Hjelmeland et al., 1977	Benzylic/substituted^2-c	0.51	−0.16
1-Phenyl-3-(4-methylphenyl)propane	Hjelmeland et al., 1977	Benzylic/substituted^2-c	0.0	−0.34
1-Phenyl-3-(4-trifluoromethylphenyl)propane	Hjelmeland et al., 1977	Benzylic/substituted^2-c	1.81	0.82

↵2-a The energy difference as determined by taking the ln of the measured ratios and multiplying by 0.616, as described under Materials and Methods.
↵2-b The energy difference between the predicted activation energy for hydrogen atom abstractions based on Eq.2.
↵2-c Benzylic hydroxylation of the phenyl ring over benzylic hydroxylation of the substituted phenyl ring.