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Title: Density functional theory study of semiquinone radical anions of polychlorinated biphenyls in the syn- and anti-like conformation.

Authors: Ambati, Jyothirmai; Song, Yang; Rankin, Stephen E; Lehmler, Hans-Joachim

Published In J Phys Chem A, (2012 Feb 16)

Abstract: Polychlorinated biphenyls (PCBs) can be metabolized to reactive metabolites, such as PCB semiquinone radical anions (SQ(ýýý-)), whose structure and role in PCB-induced toxicity are difficult to investigate due to their relative instability. The unrestricted UB3LYP/6-311G** method was used to investigate several molecular descriptors of the syn- and anti-like conformation of SQs(ýýý-). The bond lengths and angles of the quinone moiety of the SQs(ýýý-) were in between the values reported for PCB quinones and hydroquinones, which is consistent with the distribution of the ýý highest occupied molecular orbital (ýý-HOMO). The dihedral angles between the two ring systems increased in the presence of ortho chlorine substituents and were smaller compared to the corresponding PCB quinones. The ground-state energies indicate that the anti-like conformation of the SQs(ýýý-) is more favorable than the syn-like conformation. Molecular descriptor used for modeling of quantitative structure-activity relationships displayed some dependence on the conformation. These findings suggest that SQs(ýýý-) in both the syn- and antilike conformation may interact differently with target molecules, which may have implications for the toxicity of PCBs.

PubMed ID: 22257259 Exiting the NIEHS site

MeSH Terms: No MeSH terms associated with this publication

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