Complete Carcinogenic Potential of Polycyclic Fluoranthene Hydrocarbons in Relation to Their Center or Centers of Highest Electron Density

A study, of ten title compounds, was undertaken to investigate the possible use of quantum chemical DEWAR-PI molecular orbital calculations, which predict the preferred site or sites of electrophilic substitution, as a predictor of complete carcinogenic potential. These data were the basis for the development of rules of molecular geometry for predicting the center or centers of highest electron density in the molecule. Using these rules, the complete carcinogenic potentials of the hydrocarbons were predicted. These predictions were compared to the available carcinogenicity data base for this series of compounds. It is concluded that a knowledge of the center or centers of highest electron density is useful in making predictions of complete carcinogenic potential of unsubstituted title compounds. The compounds studied were fluoranthene, benzo[ghi]fluoranthene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzo[b]fluoranthene, indeno[1, 2, 3-cd]pyrene, dibenzo[a, e]fluoranthene, dibenzo[a, j]fluoranthene, benz[a]aceanthrylene and indeno[1, 2, 3-hi]-chrysene. The present study reveals that there are electronic determinants of carcinogenicity.