Chiral separation of gamma-butyrolactone derivatives by gas chromatography on 2,3-di-O-methyl-6-O-tert.-butyldimethylsilyl-beta-cyclodextrin.
The chiral GC separation of 2-alkyl-2-keto-gamma-butyrolactone derivatives and their alcohol analogs using 2,3-di-O-methyl-6-O-tert.-butyldimethylsilyl-beta-cyclodextrin (DIMETBCD) as chiral selector was discussed. The results, supported by the ketone preliminary molecular modelling calculations, suggest that the chiral recognition for DIMETBCD depends more on the geometry than on the polarity of the alkyl substituents on the butyrolactones. Hydrogen bonds and alkyl group steric effects should be an important function of the alcohol chiral recognition for DIMETBCD. Comparison of the retention times of the alcohol derivatives, in achiral and chiral stationary phases, suggests a specific structural effect for the cyclodextrin selctor.
Ramos
Maria da Conceição K V
Mda C
Laboratório de Desenvolvimento Tecnológico (LADETEC), Centro de Tecnologia, Bloco A. Sala 607, Instituto de Química, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21949-900, Brazil. cklaus@iq.ufrj.br
Teixeira
Lis H P
LH
de Aquino Neto
Francisco R
FR
Barreiro
Eliezer J
EJ
Rodrigues
Carlos R
CR
Fraga
Carlos A M
CA
D015107:4-Butyrolactone / Q000737:chemistry / Q000302:isolation & purification*; D002849:Chromatography, Gas / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D013237:Stereoisomerism; D047392:beta-Cyclodextrins
C475844:2,3-di-O-methyl-6-O-tert.-butyldimethylsilyl-beta-cyclodextrin; D003505:Cyclodextrins; D047392:beta-Cyclodextrins; D015107:4-Butyrolactone