Gas-chromatographic separation of tri(hetero)halogenomethane enantiomers

✍ Scribed by Zhengjin Jiang; Jeanne Crassous; Volker Schurig

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 199 KB
• Volume: 17
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.20191

✦ Synopsis

Abstract

Five‐atomic tri(hetero)halogenomethanes represent the simplest class of non‐isotopic small chiral molecules suitable for the study of fundamental aspects of chirality. The analytical gas‐chromatographic separation of the enantiomers of bromochlorofluoromethane 1 and of chlorofluoroiodomethane 2 on the immobilized chiral stationary phase octakis(3‐O‐butanoyl‐2,6‐di‐O‐n‐pentyl)‐γ‐cyclodextrin 3, chemically linked to polydimethylsiloxane, is described. By temperature‐dependent thermodynamic measurements very low isoenantioselective temperatures T~iso~ are found and for optimum enantiomeric separations cryogenic temperatures are required. The ee values of enantiomerically enriched tri(hetero)halogenomethanes 1 and 2 are determined and relative configurations are correlated with the chromatographic elution order of 1 and 2 on 3. © 2005 Wiley‐Liss, Inc. Chirality 17:488–493, 2005.