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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
Author(s) -
Bicchi Carlo,
Brunelli Claudio,
Cravotto Giancarlo,
Rubiolo Patrizia,
Galli Mario,
Mendicuti Francisco
Publication year - 2003
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.200301387
Subject(s) - chemistry , menthone , menthol , enantiomer , cyclodextrin , stereochemistry , monoterpene , enantioselective synthesis , organic chemistry , catalysis
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.