Density functional theoretical study of nitrated polycyclic aromatic hydrocarbons

Nitro-polycyclic aromatic hydrocarbons (nitro-PAHs) are well-known mutagens. Correlations between the orientation of the nitro group relative to the plane of the aromatic ring and mutagenic effects of nitro-PAHs have been proposed. Synthesis of specific isomers of nitro-PAHs and elucidation of their crystal structure is required to establish the validity of the structure-junction relationships. Such studies are scarce. Fortunately, electronic structure calculations can be readily done. In this study we have used density functional theory calculations to predict structure of nitro-PAHs, including 1-, 2-nitronaphthalenes; 1-, 2-, 9-nitroanthracenes; 1-, 2-, 3-, 4-, 9-nitrophenanthrenes; 1-, 2-, 4-nitropyrenes; and 6-nitrochrysene. The relationships between the calculated structures and the mutagenicity reported in the chemical literature are discussed.