Calculated properties of arene oxides of biological interest. 1. Molecular orbital examination of simple models

Abstract

The INDO calculational formalism is shown to account for the relative ease of carbonium ion formation and for the variation in isomerization rates of some simple arene oxides. Transition-state energy differences provide a reasonable correlation with observed isomerization rates for benzene oxide, methyl-substituted benzene oxides, naphthalene 1,2-oxide, and phenanthrene 9,10-oxide.