A simple mathematical model for the effect of benzoannelation on cyclic conjugation

Abstract

In a series of earlier studies, it was established that benzoannelation in the angular (resp. linear) position relative to a ring R of a polycyclic conjugated π-electron system, increases (resp. decreases) the intensity of the cyclic conjugation in the ring R. Herein, it is shown how this regularity can be explained by means of a simple, Kekulé-structurebased argument, itself based on an idea of Randić from the 1970s.

Keywords

• cyclic conjugation
• Kekulé structure
• benzo-annelation
• local aromaticity