Journal
JOURNAL OF MOLECULAR MODELING
Volume 14, Issue 6, Pages 489-497Publisher
SPRINGER
DOI: 10.1007/s00894-008-0297-9
Keywords
electron affinity; electronic dipole polarizability; dipole moment; mutagenicity; nitrobenzo[a]pyrenes
Ask authors/readers for more resources
Ionization potential (IP), electron affinity (EA), dipole moment (mu) and electronic polarizability (alpha) 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, mu and alpha values decrease in the order 6-NBaP < 1-NBa similar to 3-NBaP, the largest mu 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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available