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An Analysis of the Reactivities of Epoxide Rings in Some Cyclic Hydrocarbons

  • Conference paper
Carcinogenesis: Fundamental Mechanisms and Environmental Effects

Part of the book series: The Jerusalem Symposia on Quantum Chemistry and Biochemistry ((JSQC,volume 13))

Abstract

The reactivities of the C-O bonds in the epoxide derivatives of several cyclic hydrocarbons are analyzed by means of ab initio self- consistent-field molecular orbital calculations. Of particular interest is the degree to which epoxide ring opening may be facilitated by either or both of two special factors: (1) The proximity, in the molecule, of a double bond, and (2) intramolecular hydrogen bonding between an appropriately oriented hydroxyl group and the epoxide oxygen. It is found that while the presence of a double bond can very markedly enhance the ease of opening both epoxide C-O bonds, no such effect can be attributed to a hydroxyl group, even when it does hydrogen bond to the epoxide. The mechanism by which a double bond can weaken the C-O bonds is not understood; it appears, however, that a hydroxyl group can interfere with it. The results of this investigation are of particular importance because of their relevance to the diol epoxides that are implicated as ultimate carcinogenic forms of several polycyclic aromatic hydrocarbons.

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Author information

Authors and Affiliations

  1. Department of Chemistry, University of New Orleans, New Orleans, LA, 70122, USA

    Peter Politzer & Peter Trefonas III

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  1. Peter Politzer
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  2. Peter Trefonas III
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Editor information

Editors and Affiliations

  1. Institut de Biologie Physico-Chimique (Fondation Edmond de Rothschild), Université Pierre et Marie Curie (Paris VI), Paris, France

    Bernard Pullman

  2. The Johns Hopkins University, Baltimore, Maryland, USA

    Paul O. P. Ts’o

  3. National Cancer Institute, Bethesda, Maryland, USA

    Harry Gelboin

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© 1980 D. Reidel Publishing Company

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Politzer, P., Trefonas, P. (1980). An Analysis of the Reactivities of Epoxide Rings in Some Cyclic Hydrocarbons. In: Pullman, B., Ts’o, P.O.P., Gelboin, H. (eds) Carcinogenesis: Fundamental Mechanisms and Environmental Effects. The Jerusalem Symposia on Quantum Chemistry and Biochemistry, vol 13. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-9104-0_6

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  • DOI: https://doi.org/10.1007/978-94-009-9104-0_6

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-009-9106-4

  • Online ISBN: 978-94-009-9104-0

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