Ideal enantiomeric resolution (Preferential Enrichment) by recrystallization of a racemic compound. V: Relationship between Preferential Enrichment and crystal structures

✍ Scribed by Hiroki Takahashi; Rui Tamura; Takanori Ushio; Yoshitaka Nakajima; Ken Hirotsu

• Book ID: 101295659
• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 190 KB
• Volume: 10
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1998)10:7<705::aid-chir17>3.0.co;2-3

✦ Synopsis

The X-ray crystal structure of (±)- [2-[4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoyl]ethyl]dimethylammonium p-nitrobenzenesulfonate [(±)-NNMe 2 ], which shows the novel enantiomeric resolution phenomenon Preferential Enrichment, has been compared with that of (±)-[2-[4-(3-ethoxy-2-hydroxypropoxy) phenylcarbamoyl]ethyl]dimethylammonium p-toluenesulfonate [(±)-NTMe 2 ], which does not show the phenomenon. The stable crystalline form of (±)-NNMe 2 is a racemic compound, while that of (±)-NTMe 2 is a mixed (disordered) crystal composed of the two enantiomers. The intermolecular hydrogen bonding mode in the crystal of (±)-NNMe 2 was very different from that of (±)-NTMe 2 .