Formation of radical cations in a model for the metabolism of aromatic hydrocarbons

To test the hypothesis that electrophilic radical cations are the major ultimate electrophilic and carcinogenic forms of benza]anthracene (BA), dibenza,h]anthracene (DBA), and benzoa]pyrene (BP), we have focused on a chemical model of metabolism which parallels and duplicates known or potential metabolites of some polycyclic hydrocarbons formed in cells. Studies of this model system show that radical cations are hardly formed, if at all, in the case of BA or DBA but are definitely formed in the cases of the carcinogen BP as well as the non-carcinogenic hydrocarbons, pyrene and perylene. We conclude that the carcinogenicities of BA, DBA, BP, pyrene, and perylene are independent of one-electron oxidation to radical cation intermediates.