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Structure of trans-Isoshinanolone in the Crystal and in Solution
-
Gerhard Bringmann
,
Robert-Michael Pfeifer
Published/Copyright:
June 2, 2014
Abstract
The first X-ray structure analysis of authentic, not derivatized (racemic) trans-isoshinanolone, a wide-spread acetogenic tetralone, is described. In the crystal, two slightly different conformers are found, along with the corresponding enantiomers. The ‘homomeric’ conformers differ by their H-bonding interactions with the respective neighboring molecules. Rows of a single enantiomeric species, but with the two conformers linked ‘head-to-head’, ‘tail-to-tail’, are surrounded by four analogous rows of the corresponding enantiomers. Apparently the interactions between these heterochiral rows are the reason for the enhanced crystallization tendency of the racemate as compared to that of enantiomerically pure isoshinanolone. The structures in the crystal are compared with those calculated (gas phase) and with the structure in solution.
Received: 2003-9-29
Published Online: 2014-6-2
Published in Print: 2004-1-1
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
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Keywords for this article
Natural Products;
Crystal Structure;
Quantum Chemical Calculations;
NMR Methods
Articles in the same Issue
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- Atomvolumen, Packungsdichte und chemische Bindung in festem Iod unter Druck / Atomic Volume, Packing Density and Chemical Bonding in Solid Iodine under Pressure
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