Prediction of mutagenic activity of nitrophenanthrene and nitroanthracene isomers by simulated IR and Raman spectra

Abstract: This paper expands upon our original work on nitroanthracenes in (Alparone, A., Librando, V., 2012. Spectrochim. Acta A 89, 129–136) on the series of nitrophenanthrene isomers. Geometries, electric properties, IR and Raman spectra of 1-, 2-, 3-, 4- and 9-nitrophenanthrene (1-NP, 2-NP, 3-NP, 4-NP and 9-NP) were obtained and analyzed using Density Functional Theory calculations. The balance between steric and π-conjugative interactions determines the order of stability 4-NP < 1-NP ∼ 9-NP < 2-NP ∼ 3-NP. IR and Raman spectral zones between 1000 and 1600cm−1 show intense bands noticeably affected by the position of the substituent, being potentially useful to discriminate and monitor the investigated isomers. Dipole moments, summations of IR intensity (ΣI IR) and Raman activity (ΣA Raman) over the 3N-6 vibrational modes are sensitive to the structure, increasing steadily from the non-planar to the planar isomers. Good linear relationships between the ΣI IR (r =0.90) and ΣA Raman (r =0.99) against the Salmonella typhimurium strain TA98 mutagenic activity of nitrophenanthrenes and isomeric nitroanthracenes are found. On the basis of the structural and vibrational properties, 4-NP seems to have not mutagenic activity, while the unknown TA98 mutagenic potency of 1-nitroanthracene is predicted to be between that of 9-NP and 3-NP. Calculated ΣI IR and ΣA Raman values could be used as molecular descriptors for QSARs applications of series of isomers. [Copyright &y& Elsevier]