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Chromatographia

, Volume 58, Issue 1–2, pp 43–46 | Cite as

Monochloro-Substituted Phenyl Carbamoylated β-Cyclodextrins as π-Acid Chiral Stationary Phases for High-Performance Liquid Chromatography

  • Zheng Wu Bai
  • Chi Bun Ching
  • Siu Choon Ng
Article
  • 69 Downloads

Summary

Three π-acid type chiral stationary phases based on monochloro-substituted phenyl carbamates of β-cyclodextrin have been synthesized. First, β-cyclodextrin was reacted with 5-bromo-1-pentene in dry DMF at room temperature to give 6A-O-(4′-pentenyl)-β-cyclodextrin. The remaining twenty hydroxyl groups of this derivatized β-cyclodextrin were blocked by further reaction with 2-chlorophenyl isocyanate, 3-chlorophenyl isocyanate, and 4-chlorophenyl isocyanate in dry pyridine, at 85 °C, to yield the three corresponding carbamates. After hydrosilylation with triethoxysilane at 80 °C, catalysed by tetra(triphenylphosphine)platinum(0), these carbamates were anchored on to silica gel by heating under reflux in toluene. All the β-cyclodextrin derivatives and CSPs prepared were characterized by IR and 1H NMR spectroscopy and elemental analysis. The surface concentrations of 2-chlorophenyl carbamoylated β-cyclodextrin, 3-chlorophenyl carbamoylated β-cyclodextrin, and 4-chlorophenyl carbamoylated β-cyclodextrin on silica gel were 0.27, 0.28 and 0.30 μmol m–2, respectively. Under normal-phase conditions the separation ability of CSPs containing 3- and 4-chlorophenyl carbamate was better than that of the CSPs containing 2-chlorophenyl carbamate.

Key Words

Column liquid chromatography Enantioseparation Chiral stationary phase Monochloro-substituted phenyl carbamate β-Cyclodextrin 

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Copyright information

© Friedr. Vieweg&Sohn Verlagsgesellschaft mbH 2003

Authors and Affiliations

  1. 1.Department of PharmacyWuhan Institute of Chemical TechnologyHubei ProvincePeople's Republic of China
  2. 2.Chemical and Process Engineering CenterNational University of SingaporeSingapore
  3. 3.Department of ChemistryNational University of SingaporeSingapore

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