A frontier orbital study of substituent effects in the deamination of N-substituted quinone di-imines

Abstract

The substituent effects on the rate constants of the acid and alkaline deamination of quinone di-imines are explained, using the frontier orbital (FO) perturbation theory. The main contributions to the perturbation energy are electrostatic and orbital interactions. The alkaline deamination is both orbital and charge controlled, whereas the acid deamination is only an orbital-controlled reaction.