Table 3

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

Compound	Reference	Regioselectivity Positions	Measured^3-a	Predicted^3-b
Ethylbenzene	White et al., 1986	Aromatic (para)/benzylic	−4.1	−3.2
Toluene	Hanzlik et al., 1984	Aromatic (meta)/benzylic	−2.3	−1.9
p-Xylene	Iyer et al., 1997	Aromatic (ortho)/benzylic	−2.2	−2.3
o-Xylene	Iyer et al., 1997	Aromatic (para)/benzylic	−1.5	−1.8
Anisole	Hanzlik et al., 1984	Aromatic (meta)/O-demethylation	−0.9	−0.6
Toluene	Hanzlik et al., 1984	Aromatic (ortho)/benzylic	−0.9	−1.7
Toluene	Hanzlik et al., 1984	Aromatic (para)/benzylic	−0.6	−1.4
2-Methylanisole	Higgins et al., 2001	Aromatic (para)/O-demethylation	0.17	0.5
Anisole	Hanzlik et al., 1984	Aromatic (ortho)/O-demethylation	0.25	0.7
Anisole	Hanzlik et al., 1984	Aromatic (para)/O-demethylation	1.02	0.8

↵3-a The energy difference in kcal/mol as determined by taking the ln of the measured ratios and multiplying by 0.616, as described under Materials and Methods.
↵3-b The energy difference between the predicted activation energy for aromatic addition based on Eq. 3 and the predicted activation energy for hydrogen atom abstractions based on Eq. 2.