Electronic properties of environmental pollutants and their mutagenic activity: Nitro derivatives of azaphenanthrenes

The physico-chemical properties of nitroazaphenanthrene isomers: 4-nitro-9-azaphenanthrene (4-N-9-Aph), 5-nitro-9-azaphenanthrene (5-N-9-Aph), 6-nitro-4-azaphenanthrene (6-N-4-Aph), 8-nitro-1-azaphenanthrene (8-N-1-Aph), and 8-nitro-4-azaphenanthrene (8-N-4-Aph) have been investigated theoretically using Density Functional Theory (DFT) calculations. Equilibrium geometries, relative stability, ionization potentials, electron affinities, molecular electrostatic potentials, dipole moments, electric polarizabilities, and vibrational properties of these isomers are presented. Averaged O-N-C-C dihedral angle, dipole moment, polarizability, the summation of IR intensities (∑IIR) and the summation of Raman activities (∑ARaman) over all 3N-6 vibrational degrees of freedom are sensitive to the structure of isomers. A very good linear relationship between ∑ARaman values (R = 1.00) and the Salmonella typhimurium strain TA98(−S9) mutagenic activity of the investigated nitroazaphenanthrene isomers (Tokiwa et al., 2003) reveals a very important role of inductive and dispersive forces on the mutagenic pathways of the investigated isomers.