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Structure of trans-Isoshinanolone in the Crystal and in Solution

Title data

Bringmann, Gerhard ; Pfeifer, Robert-Michael ; Breuning, Matthias ; Reichert, Matthias ; Messer, Kim ; Schraut, Michaela ; Tóth, Gabor:
Structure of trans-Isoshinanolone in the Crystal and in Solution.
In: Zeitschrift für Naturforschung B. Vol. 59 (2014) Issue 1 . - pp. 100-105.
ISSN 1865-7117
DOI: https://doi.org/10.1515/znb-2004-0114

Abstract in another language

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.

Further data

Item Type: Article in a journal
Refereed: Yes
Keywords: Natural Products; Crystal Structure; Quantum Chemical Calculations; NMR Methods
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 12 Jan 2022 08:02
Last Modified: 12 Jan 2022 08:02
URI: https://eref.uni-bayreuth.de/id/eprint/68328