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


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.



  1. Chrial Seperation by HPLC Ariens, E. J.;Krstulovic, A. M.(Ed.)
  2. Tetrahedron Lett. Gil-Av, E.;Feibush, B.;Charls-sigler, R.
  3. J. Chromatogr v.112 Charles, R.;Gil-Av, E.
  4. J. Chromatogr v.195 Charles, R.;Gil-Av, E.
  5. Anal. Chem. v.47 Konig, W. A.;Nicholson, G. J.
  6. Tetrahedron v.26 Feibush, B.;Gil-Av, E.
  7. J. Chromatogr. v.207 Oi, N.;Kitohara, H.;Doi, T.
  8. J. Chromatogr. v.254 Oi, N.;Kitohara, H.;Doi, T.
  9. CRC Crit. Rev. Anal. Chem. v.19 Armstrong, D. W.;Han, S. M.
  10. J. Chromatogr. Sci. v.15 Frank, H.;Nicholson, C. J.;Bayer, E.
  11. The Science of Chromatography Koppenhoefer, B.;Bayer, E.;Bruner, F.(Ed.)
  12. J. Chromatogr. v.251 Smolkova-Keulemansova, E.
  13. J. Chromatogr. v.241 Smolkova-Keulemansova, E.;Kratova, H.;Krysl, S.;Feltl, L.
  14. J. Chromatogr. v.349 Krysl, S.;Smolkova-Keulemansova, E.
  15. J. Inclus Phenom v.3 Smolkova-Keulemansova, E.;Feltl, L.;Krysl, S.
  16. J. Chromatogr. v.280 Koscielski, T.;Sybilska, D.;Jurczak, J.
  17. Chromatographia v.21 Koscielski, T.;Sybilska, D.;Belniak, B.;Jurczak, J.
  18. J. Chromatogr. v.441 Schuring, V.;Novotny, H. P.
  19. Angew. Chem. v.101 Schurig, V.;Novotny, H. P.;Schmalzing, D.
  20. J. Chromator. v.447 Koning, W. A.;Lutz, S.;Mischnik-Lublecke, P.;brassat, B.;Wenz, G.
  21. J. High Resolut Chromatogr, Chromatogr. Commun, Ⅱ Konig, W. A.;Lutz, S.;Wenz, G.;E. von der Bey
  22. J. High Resolut Chromatogr, Chromatogr. Commun, Ⅱ Konig, W. A.;Lutz, S.;Colberg, C.;Schmit, N.;Wenz, G.;E. von der Bey;Mosandl, A.;Gunther, C.;Kustermann, A.
  23. Angew. Chem. Int. Ed. Engl. v.27 Konig, W. A.;Lutz, S.;Wenz, G.
  24. Presented at the Pottsburgh Conference, Abstract Armstrong, D. W.
  25. Anal. Chem. Armstrong, D. W.;Li, W.;Pitha, J.
  26. Angew. Chem. Int. Ed. Engl. v.24 Koppenhoefer, B.;Allmendinger, H.;Nicholson, G.
  27. J. Chromatogr. v.218 Tomlinson, E.;Hafkenscheid, T. L.
  28. J. Chromatogr. v.158 Melander, A.;Campbell, W.;Horvath, D. E.
  29. Anal. Chem. v.64 Li, A. E.;Amstrong, D. W.