Volume 31, Issue 7
Natural Products
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ChemInform Abstract: (+)-3-Oxoglycyrrhetinic Acid: Catemeric Hydrogen Bonding in a Non-racemic Triterpenoid Diketo Acid.

Andrew P. J. Brunskill

Andrew P. J. Brunskill

Dep. Chem., Rutgers State Univ., Newark, NJ 07102, USA

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Hugh W. Thompson

Hugh W. Thompson

Dep. Chem., Rutgers State Univ., Newark, NJ 07102, USA

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Roger A. Lalancette

Roger A. Lalancette

Dep. Chem., Rutgers State Univ., Newark, NJ 07102, USA

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First published: 10 June 2010

Abstract

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ChemInform Abstract

All rings of title compound (I) adopt chair conformation, except the enone ring, which is flattened to a half-chair. In solid state, (I) adopts carboxyl-to-ketone catemeric hydrogen bonding, i.e. distorted hydrogen bonds from the carboxyl H atom of one molecule to the remote-ring ketone O atom of a screw-related neighbor yield helical hydrogen-bonding chains.

chemical structure image

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