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Science 5 February 1982:
Vol. 215. no. 4533, pp. 695 - 696
DOI: 10.1126/science.215.4533.695
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Articles

Internal Hydrogen Bond Formation in a syn-Hydroxyepoxide

JENNY P. GLUSKER 1, DAVID E. ZACHARIAS 1, DALE L. WHALEN 2, STEVE FRIEDMAN 2, and TERESA M. POHL 2

1 Institute for Cancer Research, Fox Chase Cancer Center, Philadelphia, Pennsylvania 19111
2 Chemistry Department, University of Maryland-Baltimore County, Baltimore 21228

The existence of an internal hydrogen bond in a compound representative of a syn diol epoxide (a possible intermediate in chemical carcinogenesis by certain polycyclic aromatic hydrocarbons) has been demonstrated by x-ray crystallographic and nuclear magnetic resonance studies. This internal hydrogen bond was found in 3,4-epoxy-2-methyl-1,2,3,4-tetrahydro-1-naphthol and was shown to persist in dioxane-water solutions containing up to 80 mole percent water. In this structure, the 1-hydroxy and 2-methyl groups are shown to occupy axial positions. In the anti diol epoxide, which has no internal hydrogen bond, analogous groups are equatorial. Crystals of the compound were unstable in the x-ray beam while the data were being collected (even at low temperatures), presumably as a result of decomposition.

Submitted on July 9, 1981
Revised on October 1, 1981


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Three-dimensional structure of anti-5,6-dimethylchrysene-1,2-dihydrodiol-3,4-epoxide: a diol epoxide with a bay region methyl group.
C. E. Afshar, A. K. Katz, H.L. Carrell, S. Amin, D. Desai, and J. P. Glusker (1999)
Carcinogenesis 20, 1549-1554
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Science. ISSN 0036-8075 (print), 1095-9203 (online)