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Cyclodextrin derivatives in GC separation of racemates with different volatilities. Part XIX: Thermodynamic aspects of enantioselective GC separation of some volatiles with γ-cyclodextrins 2,3-substituted with methyl and acetyl groups

✍ Scribed by Carlo Bicchi; Claudio Brunelli; Giancarlo Cravotto; Patrizia Rubiolo; Mario Galli; Francisco Mendicuti

Book ID
102928463
Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
944 KB
Volume
26
Category
Article
ISSN
1615-9306

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✦ Synopsis

Abstract

The thermodynamic parameters involved in the enantiomer separation of two homologous series of γ‐lactones (C~6~–C~8~ and C~10~–C~12~) and a group of structurally related monoterpenoids with a __p‐__menthane skeleton (menthol, __i‐__menthol, __neo‐__menthol, __neo‐i‐__menthol, menthone, __i‐__menthone, and 3‐oxo‐1,8‐cineole) are determined to investigate how inverted substitution in positions 2 and 3 of the cyclodextrin ring with methyl and acetyl groups influences the enantioselectivity of 2‐O‐methyl‐3‐O‐acetyl‐6‐O‐t‐hexyldimethylsilyl‐γ‐cyclodextrin and 2‐O‐acetyl‐3‐O‐methyl‐6‐O‐t‐hexyl‐dimethylsilyl‐γ‐cyclodextrin. The thermodynamic results show that the methyl and acyl groups, in positions 2 and 3 respectively, act complementarily to increase enantioselectivity and that the relative configuration of the stereogenic centres in the selectands influences enantiomer separation.

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Cyclodextrin derivatives in GC separatio
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✍ C. Bicchi; A. D'Amato; V. Manzin; A. Galli; M. Galli 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 665 KB

## Abstract The results of a series of experiments concerning the GC enantioseparation of some racemates on columns coated with 2,3‐di‐O‐acetyl‐6‐O‐t‐butyldimethylsilyl‐β‐cyclodextrin diluted in two different polysiloxanes (PS‐086 and OV‐1701) are reported. The investigation is centered on the infl

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In previous papers, 2,6-di-O-methyl-3-O-pentyl-~-cyclodextrin (CD) was demonstrated to be successful in separating volatile compounds, while avoiding the drawbacks of 2,3,6-tri-O-methyl-P-CD in terms of column stability and operating temperature. Since a CD chiral selector of universal use has not y