DENSITY FUNCTIONAL THEORETICAL STUDY OF MONO-NITRATED FLUORANTHENES

The molecules 1-, 2-, 3-, 7-, and 8-nitrofluoranthenes are well-known mutagens and carcinogens. These environmental pollutants are emitted into the atmosphere via anthropogenic activities including diesel combustion emissions, residential home heating and reactions of nitrogen oxide (NOx) gases with fluoranthene. The differential mutagenic potency between nitrated fluoranthenes has been proposed to emanate from the orientation of the nitro group relative to the aromatic plane. To establish the validity of the structure-function correlations requires specific crystal structures, which are unavailable. Fortunately, electronic structure calculations can be done. In this report, the structures of fluoranthene and its mono nitrated derivatives were investigated with the density functional theoretical theory at B3LYP/6-311+G** level. The structure-function correlations were examined by comparing reported mutagenicity data with calculated bond lengths, angles and dihedral angles. The relationships between the calculated structures and the reported mutagenicity in the chemical literature are discussed.