title: Self-disproportionation of enantiomers via achiral gravity-driven column chromatography: A case study of N-acyl-α-phenylethylamines.
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.
authors.affiliation: Institute 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. Electronic address: alicja.wzorek@ujk.edu.pl.
authors.forename: Alicja
authors.initials: A
authors.lastname: Wzorek
authors.affiliation: Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain; Department of Chemistry, Tokyo Women's Medical University, 8-1 Kawada-cho, Shinjuku-ku, 162-8666 Tokyo, Japan.
authors.forename: Azusa
authors.initials: A
authors.lastname: Sato
authors.affiliation: Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland; Institute of Chemistry, Environmental Protection and Biotechnology, Jan Długosz University in Częstochowa, Armii Krajowej 13/15, 42-201 Częstochowa, Poland.
authors.forename: Józef
authors.initials: J
authors.lastname: Drabowicz
authors.affiliation: Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain; IKERBASQUE, Basque Foundation for Science, Alameda Urquijo 36-5, Plaza Bizkaia, 48011 Bilbao, Spain. Electronic address: vadym.soloshonok@ehu.eus.
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
mesh_terms: D000577:Amides / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D006112:Gravitation; D006801:Humans; D006860:Hydrogen Bonding; D010627:Phenethylamines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D010627:Phenethylamines
keywords: Amide bond; Enantiopurification; Gravity-driven column chromatography; Homo/hetero-chiral intermolecular interaction; SDE (self-disproportionation of enantiomers); SDE-phoric groups