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Title: Monochloro-substituted phenyl carbamoylated β-cyclodextrins as π-acid chiral stationary phases for high-performance liquid chromatography
Authors: Bai, Z.W.
Ching, C.B. 
Ng, S.C. 
Keywords: β-Cyclodextrin
Chiral stationary phase
Column liquid chromatography
Monochloro-substituted phenyl carbamate
Issue Date: Jul-2003
Citation: Bai, Z.W.,Ching, C.B.,Ng, S.C. (2003-07). Monochloro-substituted phenyl carbamoylated β-cyclodextrins as π-acid chiral stationary phases for high-performance liquid chromatography. Chromatographia 58 (1-2) : 43-46. ScholarBank@NUS Repository.
Abstract: 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 ond 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.
Source Title: Chromatographia
ISSN: 00095893
Appears in Collections:Staff Publications

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