Why are the kinked polyacenes more stable than the straight ones? A topological study and introduction of a new topological index of aromaticity

J Chem Inf Model. 2008 Jul;48(7):1358-66. doi: 10.1021/ci800061q. Epub 2008 Jun 12.

Abstract

A topological model for estimating the stability of benzenoid hydrocarbons (BHs) is presented showing an acceptable linear dependence on Hess-Schaad resonance energy per pi-electron values. The topological measure of stability is accessible by use of pencil calculation and is based on counting cis-type fragments of double bonds in all canonical structures of a given BH. Evidence is given that infinite chains of straight linear polyacenes are always less stable than the kinked ones.

MeSH terms

  • Molecular Structure
  • Polycyclic Compounds / chemistry*

Substances

  • Polycyclic Compounds