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Carbon-13 and Proton Magnetic Resonance Studies of Chlorinated Biphenyls

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Mass Spectrometry and NMR Spectroscopy in Pesticide Chemistry

Part of the book series: Environmental Science Research ((ESRH,volume 4))

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Abstract

13C and 1H nuclear magnetic resonance spectra were obtained for ten symmetric chlorinated biphenyls and for 4,4′ disubstituted biphenyls with NH1H, CH3O, CH3, Cl, F and N02 substituents. The 1H shieldings are shown to correlate with π electron densities calculated by the CNDO/2 method, if corrections are made for ring current effects from the second ring. For freely rotating biphenyls, additive substituent parameters obtained from benzene data predict the 13C shieldings with reasonable precision. Steric hindrance to rotation by substituents at the 2,6,2′ and/or 6′ positions causes deviations from the substituent effects predicted by additivity; these deviations in δC are especially pronounced for the carbons at positions land 1′. The total charge correlation with δC in substituted benzenes is also valid in non-hindered substituted biphenyls. Small differences in δC between chlorinated biphenyl isomers are best related to differences in the calculated σ electron densities.

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Authors and Affiliations

  1. National Institute of Environmental Health Sciences, P. O. Box 12233, Research Triangle Park, N. C., 27709, USA

    Nancy K. Wilson & Marshall Anderson

Authors
  1. Nancy K. Wilson
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  2. Marshall Anderson
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Editors and Affiliations

  1. Department of Agricultural Chemistry and Environmental Health Sciences Center, Oregon State University, Corvallis, Oregon, 97331, USA

    Rizwanul Haque

  2. Primate & Pesticides Effects Laboratory, U.S. Environmental Protection Agency, Perrine, Florida, 33157, USA

    Francis J. Biros

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© 1974 Springer Science+Business Media New York

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Wilson, N.K., Anderson, M. (1974). Carbon-13 and Proton Magnetic Resonance Studies of Chlorinated Biphenyls. In: Haque, R., Biros, F.J. (eds) Mass Spectrometry and NMR Spectroscopy in Pesticide Chemistry. Environmental Science Research, vol 4. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-4526-8_15

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  • DOI: https://doi.org/10.1007/978-1-4613-4526-8_15

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-4528-2

  • Online ISBN: 978-1-4613-4526-8

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