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Electronic properties of some nitrobenzo[a]pyrene isomers: a possible relationship to mutagenic activity

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Abstract

Ionization potential (IP), electron affinity (EA), dipole moment (μ) and electronic polarizability (α) of 1-, 3- and 6-nitrobenzo[a]pyrene isomers (1-NBaP, 3-NBaP, 6-NBaP) were determined by using density functional theory (DFT) and recent semiempirical PM6 methods. Calculated IP value remains almost constant along the series of isomers, while EA value depends on the nitro group position, increasing by ca. 0.2 eV on passing from 6- to 1-NBaP (or 3-NBaP) isomer. Stability, μ and α values decrease in the order 6-NBaP < 1-NBa ∼ 3-NBaP, the largest μ variation being predicted to be 1.5 D (30%) by DFT computations. The results obtained herein are consistent with the observed greater mutagenic activity of 3- and 1-NBaP in comparison to 6-NBaP isomer, suggesting that both binding to enzyme, which depends on electric properties, and reduction process, which is related to EA value may be crucial steps in the mutagenic mechanism of this series of isomers.

Structure and dipole moment vector of nitrobenzo[a]pyrene isomers

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Acknowledgements

This work was carried out in the framework of the RIC action of the Project No. 1999/IT.16.1.PO.011/3.13/7.2.4/339 PROT. 238, “Formazione per la ricerca nel campo della bonifica dei siti contaminate” POR Sicilia 2000–2006, Asse: III Misura: 3.13.

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  1. Department of Chemistry, University of Catania, Viale A. Doria 8, I-95125, Catania, Italy

    Vito Librando & Gaetano Tomaselli

  2. Research Centre for Analysis, Monitoring and Minimization Methods of Environmental Risk and Department of Chemistry, University of Catania, Viale A. Doria 8, I-95125, Catania, Italy

    Andrea Alparone

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  1. Vito Librando
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Correspondence to Vito Librando.

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Librando, V., Alparone, A. & Tomaselli, G. Electronic properties of some nitrobenzo[a]pyrene isomers: a possible relationship to mutagenic activity. J Mol Model 14, 489–497 (2008). https://doi.org/10.1007/s00894-008-0297-9

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