Effect of a substituent on an aromatic group in diastereomeric resolution

Citation
K. Kinbara et al., Effect of a substituent on an aromatic group in diastereomeric resolution, TETRAHEDRON, 56(36), 2000, pp. 6651-6655
Citations number
15
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
0040-4020 → ACNP
Volume
56
Issue
36
Year of publication
2000
Pages
6651 - 6655
Database
ISI
SICI code
0040-4020(20000901)56:36<6651:EOASOA>2.0.ZU;2-Q
Abstract
The diastereomeric resolution of p-substituted 1-arylethylamines by enantio pure (S)-3',4'-methylenedioxymandelic acid ((S)-2) was carried out in order to know how an electron-donating or -withdrawing group on the aromatic gro up of the racemic amines would affect the efficiency of resolution. As a re sult, it was found that 1-arylethylamines having an electron-withdrawing su bstituent could be efficiently resolved by (S)-2, while the amines having a n electron-donating group could not. The crystal structures of the less- an d more-soluble salts, and the molecular orbital calculations of the ammoniu m cations indicated that the p-substituted electron-withdrawing group enhan ced the positive charge on the meta-hydrogen of the aromatic group of the a mmonium cations, which is favorable for the formation of a CH ...pi interac tion in crystal. (C) 2000 Elsevier Science Ltd. All rights reserved.