Cyclodextrin carbamates as novel chiral stationary phases for capillary gas chromatography

✍ Scribed by Takeichi, Tsutomu ;Toriyama, Hisashi ;Shimura, Shigeru ;Takayama, Yuzi ;Morikawa, Masami

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 743 KB
• Volume: 18
• Category: Article
• ISSN: 0935-6304
• DOI: 10.1002/jhrc.1240180309

✦ Synopsis

Abstract

The following carbamate derivatives of cyclodextrins (CDs) were prepared as novel chiral stationary phases for capillary gas chromatography: hexakis(2,6‐di‐O‐pentyl)‐α‐cyclodextrin hexa(3‐n‐propyl, 3‐isopropyl, and 3‐phenylcarbamate), heptakis‐(2,6‐di‐O‐pentyl)‐β‐cyclodextrin hepta(3‐n‐propyl, 3‐isopropyl, and 3‐phenylcarbamate), and octakis(2,6‐di‐O‐pentyl)‐γ‐cyclodextrin octa(3‐n‐propyl, 3‐isopropyl, and 3‐isopropyl, and 3‐phenylcarbamate). Metal capillary columns coated with these stationary phases resolved many kinds of racemic mixture. In general, they were especially effective towards polar compounds such as free alcohols, amines, and epoxides. The types of sample which were effectively resolved depended on the cavity size of the CD: α‐CD derivatives were specifically effective toward compounds having linear alkyl chains, and β‐CD derivatives toward compounds with phenyl groups. The results indicate that chiral separation with the cyclodextrin carbamates depends on the formation of inclusion complexes and also on the hydrogen‐bonding interactions between the samples and the CD carbamates.