IDEAL ENANTIOMERIC RESOLUTION (PREFERENTIAL ENRICHMENT) BY RECRYSTALLIZATION OF A RACEMIC COMPOUND - V - RELATIONSHIP BETWEEN PREFERENTIAL ENRICHMENT AND CRYSTAL-STRUCTURES

Authors
TAKAHASHI H TAMURA R USHIO T NAKAJIMA Y HIROTSU K
Citation
H. Takahashi et al., IDEAL ENANTIOMERIC RESOLUTION (PREFERENTIAL ENRICHMENT) BY RECRYSTALLIZATION OF A RACEMIC COMPOUND - V - RELATIONSHIP BETWEEN PREFERENTIAL ENRICHMENT AND CRYSTAL-STRUCTURES, Chirality, 10(7), 1998, pp. 705-710
Citations number
6
Categorie Soggetti
Chemistry Medicinal","Chemistry Analytical","Chemistry Inorganic & Nuclear","Pharmacology & Pharmacy
Journal title
Chirality → ACNP
ISSN journal
08990042
Volume
10
Issue
7
Year of publication
1998
Pages
705 - 710
Database
ISI
SICI code
0899-0042(1998)10:7<705:IER(EB>2.0.ZU;2-#
Abstract
The X-ray crystal structure of (+/-)-[2-[4-(3-ethoxy-2-hydroxypropoxy) phenylcarbamoyl] ethyl] dimethylammonium p-nitrobenzenesulfonate [(+/ -)-NNMe2], which shows the novel enantiomeric resolution phenomenon Pr eferential Enrichment, has been compared with that of (+/-)-[2-[4-(3-e thoxy-2-hydroxypropoxy) phenylcarbamoyl] ethyl] dimethylammonium p-tol uenesulfonate [(+/-)-NTMe2], which does not show the phenomenon. The s table crystalline form of (i)-NNMe2 is a racemic compound, while that of (+/-)-NTMe2 is a mixed (disordered) crystal composed of the two ena ntiomers. The intermolecular hydrogen bonding mode in the crystal of ( +/-)-NNMe2 was very different from that of (+/-)-NTMe2. (C) 1998 Wiley -Liss, Inc.