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Published on: August 18, 2017
Gas-chromatographic separation of tri(hetero)halogenomethane enantiomers
Zhengjin Jiang1, Jeanne Crassous, Volker Schurig
1Institute of Organic Chemistry, University of Tübingen, Morgenstelle 18, D-72076 Tübingen, Germany.
Abstract:
Five-atomic tri(hetero)halogenomethanes represent the simplest class of non-isotopic small chiral molecules suitable for the study of fundamental aspects of chirality. The analytical gas-chromatographic separation of the enantiomers of bromochlorofluoromethane 1 and of chlorofluoroiodomethane 2 on the immobilized chiral stationary phase octakis(3-O-butanoyl-2,6-di-O-n-pentyl)-gamma-cyclodextrin 3, chemically linked to polydimethylsiloxane, is described. By temperature-dependent thermodynamic measurements very low isoenantioselective temperatures T(iso) are found and for optimum enantiomeric separations cryogenic temperatures are required. The ee values of enantiomerically enriched tri(hetero)halogenomethanes 1 and 2 are determined and relative configurations are correlated with the chromatographic elution order of 1 and 2 on 3.
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