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KMID : 1059519950390020094
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Journal of the Korean Chemical Society
1995 Volume.39 No. 2 p.94 ~ p.102
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Chiral Separation of Derivatized Racemic Alcohols on Substitued Cyclodextrin Stationary Phases by Capillary Gas Chromatography
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Lee Sun-Haing
Seo Yeong-Ju
Lee Kwang-Pill
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Abstract
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S-Hydroxypropyl(PH) β-cyclodextrin(hydrophilic), dialkyl(DA)-cyclodextrin(hydrophobic), trifluoroacetyl(TA) γ-cyclodextrin(intermediate) stationary phases were used for gas chromatographic separation of racemic alcohols and their derivatives. All the alcohols used for this exeriment were derivatived by using trifluoro acetic anhydride, acetic anhydride, or trichloro acetic anhydride. It is apparent that the enantioselectivity of the enantiomeric pairs was very dependent on the type of acylation reagent. The best experimental condition of optical resolution of the alcohols and their derivatives was different on the polarity of the solute molecules. The chiral separation was also studied depending on temperature, polarity of the column, and hydrogen bonding ability and steric effect between the alchols and CD stationary phase. The chiral recognition mechanism is dependent not upon the kinds of the chiral stationay phases but upon the derivatization of the racemic alchols.
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