Combinatorial Enumeration of Isomers of Superaromatic Polysubstituted Cycloarenes and Coronoid Hydrocarbons with Applications to NMR.

Abstract

We have employed combinatorial techniques based on character cycle indices, Pólya's theory, and Euler totem function to enumerate isomers of polysubstituted cycloarenes and coronoid hydrocarbons which have been receiving considerable attention because of their superaromaticity, ring currents, and interesting magnetic properties. Systematic enumeration and construction of tables of polysubstituted isomers such as fluoro-chloro superaromatic hydrocarbons are considered as they are of interest in the study of environmental pollutants and toxicity. Isomers of fluoro-chloro polysubstituted donut shaped circumkekulenes, circumseptulenes, circumoctulenes, etc., are enumerated in addition to other cycloarenes, polycyclic circumcoronaphenes and coronoids. Applications to 13C NMR, proton NMR and multiple quantum NMR spectroscopies of these superaromatic species are considered.