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The application of empirical methods of 13 C NMR chemical shift prediction as a filter for determining possible relative stereochemistry
Author(s) -
Elyashberg Mikhail E.,
Blinov Kirill A.,
Williams Antony J.
Publication year - 2009
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2396
Subject(s) - chemistry , chemical shift , stereocenter , quantum chemical , derivatization , computational chemistry , molecule , organic chemistry , high performance liquid chromatography , enantioselective synthesis , catalysis
The reliable determination of stereocenters contained within chemical structures usually requires utilization of NMR data, chemical derivatization, molecular modeling, quantum‐mechanical (QM) calculations and, if available, X‐ray analysis. In this article, we show that the number of stereoisomers which need to be thoroughly verified, can be significantly reduced by the application of NMR chemical shift calculation to the full stereoisomer set of possibilities using a fragmental approach based on HOSE codes. The applicability of this suggested method is illustrated using experimental data published for a series of complex chemical structures. Copyright © 2009 John Wiley & Sons, Ltd.