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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The hydroxyl stretching frequencies and conformations of Flavan-4-ols and Thiaflavan-4-ols

GF Katekar and AG Moritz

Australian Journal of Chemistry 22(11) 2337 - 2342
Published: 1969

Abstract

The hydroxyl stretching frequencies of some 2,4-cis and 2,4-trans flavan-4-ols, thiaflavan-4-ols, and related compounds have been measured in dilute carbon tetrachloride solution. Characteristic frequencies are observed at 3626±2 cm-1 (free hydroxyl), 3616±1, and 3597±2 cm-1. The 3616 and 3597 cm-1 bands are assigned to pseudo-axial and pseudo-equatorial hydroxyl groups respectively. Evidence is presented to show that the frequency shifts arise from differences in the interaction of the hydroxyl group with the π-electrons of the fused benzene ring, and that these flavans and thiaflavans exist in half- chair, rather than sofa conformations.

https://doi.org/10.1071/CH9692337

© CSIRO 1969

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