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Published on: August 18, 2017
Self-disproportionation of enantiomers via achiral gravity-driven column chromatography: A case study of
Alicja Wzorek1, Azusa Sato2, Józef Drabowicz3
1Institute of Chemistry, Jan Kochanowski University in Kielce, Świętokrzyska 15G, 25-406 Kielce, Poland; Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain.
Abstract:
Herein we report a study of the self-disproportionation of enantiomers (SDE) via gravity-driven achiral column chromatography of a series of amides derived from 1-phenylethylamine. We demonstrated that structural and electronic factors of the substituents play an important role in the observed magnitude of the SDE. For the first time, the SDE phenomenon of amides with that of thioamides was compared. We demonstrate that, in sharp contrast to amides, the substitution of the sulphur atom for the oxygen in the acyl group, strongly reduced the observed magnitude of the SDE. These results clearly indicate the importance of the hydrogen bonding for the formation of homo/hetero-chiral association responsible for manifestation of the SDE phenomenon.
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