Correlations between local aromaticity indices of bipartite conjugated hydrocarbons

Abstract

Local aromaticity in rings of conjugated hydrocarbons can be measured in a variety of ways. In the present paper, we concentrate on two of these, namely, EC, i.e., the π-electron content or π-electron partition, and ef, the energy effect of cycles. For the central ring in five bipartite conjugated hydrocarbons (anthracene, triphenylene, perylene, coronene, and biphenylene), it was found that EC and ef values are modified in a consistent and predictable manner by annelation with benzenoid rings. Equations are presented for computing EC and ef values for the central ring in terms of three integers representing the numbers of annelated benzenoid rings (A, L, and G for angular, linear, and geminal annelation, respectively). The coefficients of A and G are positive (A > G) and the coefficient of L is negative for benzenoids, but for biphenylene, the situation is reversed for coefficients in the correlation for ef values. © 2010 American Chemical Society.