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Updated: Jun 18, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
Published on: August 18, 2017
Structural determination of molecular stereochemistry using VCD spectroscopy and a conformational code: absolute
Hiroshi Izumi1, Atsushi Ogata, Laurence A Nafie
1National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba West, Tsukuba, Ibaraki, Japan. izumi.h@aist.go.jp
Abstract:
The absolute configuration and solution conformation of (R)-(+)-malathion were determined by using vibrational circular dichroism spectroscopy and a fragment-conformational search with a recently published conformational code. The determination of molecular stereochemistry was carried out without a conformational search using molecular mechanics calculations. Density functional theory calculations of the fragments of (R)-malathion, ethyl propionate, (R)-ethyl 2-(methylthio)propanoate, (R)-diethyl 2-(methylthio)succinate, and O,O,S-trimethyl phosphorodithioate were carried out, and the principal conformational features of the fragments were profiled. This fragment-conformational search reduces the time needed for the selection of the predominant conformations for (R)-malathion and significantly improves the accuracy of the determination of absolute configuration.
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