Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Chiral Separation of Derivatized Racemic Alcohols on Substitued Cyclodextrin Stationary Phases by Capillary Gas Chromatography

모세관 기체 크로마토그래피에 의한 치환된 Cyclodextrin 정지상을 이용한 알코올 유도체의 키랄분리

  • Lee, Sun-Haing (Department of Chemistry Education, Kyungpook National University) ;
  • Seo, Yeong-Ju (Department of Chemistry Education, Kyungpook National University) ;
  • Lee, Kwang-Pill (Department of Chemistry Education, Kyungpook National University)
  • 이선행 (경북대학교 사범대학 화학교육과) ;
  • 서영주 (경북대학교 사범대학 화학교육과) ;
  • 이광필 (경북대학교 사범대학 화학교육과)
  • Published : 19950200
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Abstract

S-Hydroxypropyl(PH) ${\beta}$-cyclodextrin(hydrophilic), dialkyl(DA)-cyclodextrin(hydrophobic), trifluoroacetyl(TA) ${\gamma}$-cyclodextrin(intermediate) stationary phases were used for gas chromatographic separation of racemic alcohols and their derivatives. All the alcohols used for this experiment 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.

모세관 기체크로마토그래피에 의한 cyclodextrin 정지상들(PH-${\beta}$-CD, DA-${\beta}$-CD, TA-${\gamma}$-CD)을 이용하여 라세미 알코올들과 그 유도체들의 분리를 연구하였다. 실험에 사용한 모든 알코올들은 trifluoro acetic anhydride, acetic anhydride, trichloro acetic anhydride를 써서 유도화하였다. 거울상체들의 분리선택성은 acylation 시약의 형태에 상당히 의존하는 것을 알았다. 알코올과 그 유도체들의 광학분활에 대한 최상의 실험조건은 용질분자들의 극성에 따라 다르다. 그리고 키랄분리에 관해서 온도, 컬럼이 극성, 수소 결합력, 알코올과 CD 정지상의 입체효과 등의 의존에 관한 연구를 행하였다. 키랄 인식 기구는 키랄 정지상의 종류에 의존하지 않고, 라세미 알코올의 유도체화에 의존하는 것으로 나타났다.

Keywords

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