| Density functional theory study of semiquinone radical anions of polychlorinated biphenyls in the syn- and anti-like conformation. | |
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MedLine Citation:
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PMID: 22257259 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Polychlorinated biphenyls (PCBs) can be metabolized to reactive metabolites, such as PCB semiquinone radical anions (SQ(•-)), 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(•-). The bond lengths and angles of the quinone moiety of the SQs(•-) were in between the values reported for PCB quinones and hydroquinones, which is consistent with the distribution of the α highest occupied molecular orbital (α-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(•-) 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(•-) in both the syn- and antilike conformation may interact differently with target molecules, which may have implications for the toxicity of PCBs. |
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Authors:
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Jyothirmai Ambati; Yang Song; Stephen E Rankin; Hans-Joachim Lehmler |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2012-02-06 |
Journal Detail:
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Title: The journal of physical chemistry. A Volume: 116 ISSN: 1520-5215 ISO Abbreviation: J Phys Chem A Publication Date: 2012 Feb |
Date Detail:
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Created Date: 2012-02-20 Completed Date: 2012-08-28 Revised Date: 2013-02-22 |
Medline Journal Info:
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Nlm Unique ID: 9890903 Medline TA: J Phys Chem A Country: United States |
Other Details:
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Languages: eng Pagination: 1586-95 Citation Subset: IM |
Affiliation:
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Department of Chemical and Materials Engineering, University of Kentucky, Lexington, Kentucky 40506-0046, United States. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Benzoquinones
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chemistry* Diffusion Models, Molecular Molecular Conformation Polychlorinated Biphenyls / chemistry*, toxicity Quantitative Structure-Activity Relationship Quantum Theory* Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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ES013661/ES/NIEHS NIH HHS; ES017425/ES/NIEHS NIH HHS; ES05605/ES/NIEHS NIH HHS; P30 ES005605-17/ES/NIEHS NIH HHS; P30 ES005605-18/ES/NIEHS NIH HHS; P30 ES005605-19/ES/NIEHS NIH HHS; P30 ES005605-20/ES/NIEHS NIH HHS; P42 ES013661-02/ES/NIEHS NIH HHS; P42 ES013661-03/ES/NIEHS NIH HHS; P42 ES013661-04/ES/NIEHS NIH HHS; P42 ES013661-05/ES/NIEHS NIH HHS; P42 ES013661-06/ES/NIEHS NIH HHS; P42 ES013661-07/ES/NIEHS NIH HHS; R01 ES017425/ES/NIEHS NIH HHS; R01 ES017425-01A1/ES/NIEHS NIH HHS; R01 ES017425-02/ES/NIEHS NIH HHS; R01 ES017425-03/ES/NIEHS NIH HHS; R01 ES017425-04/ES/NIEHS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Benzoquinones; 0/Polychlorinated Biphenyls; 3225-29-4/semiquinone radicals |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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