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1H NMR studies on mutagenic nitrofluoranthenes and exposure risk assessment.

The 1H NMR spectra of the nitrofluoranthene isomers are presented to allow gas chromatographic analysis of environmental samples suspected of containing nitrofluoranthenes. The mutagenic isomers 1-, 2-, 3-, 7-, and 8-nitrofluoranthene and 1,2- and 1,3-dinitrofluoranthene and a nonmutagenic analogue, 1-phenyl-4-nitronaphthalene, have been studied by using nuclear Overhauser effects and 2D shift-correlated 1H NMR spectroscopy. The X-ray crystal structure of 1-phenyl-4-nitronaphthalene is also reported. Reduction potentials and coplanarity of the nitro group have been used to correlate the mutagenicity of nitrated polycyclic aromatic hydrocarbons (nitro-PAH) measured by the Ames assay, but our data suggest that these parameters are not sufficient for the prediction of mutagenic potency in the nitrofluoranthene series.