Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/92147
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
Enantioseparation
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
URI: http://scholarbank.nus.edu.sg/handle/10635/92147
ISSN: 00095893
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.

Page view(s)

35
checked on Oct 19, 2018

Google ScholarTM

Check


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.