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Reference type: Journal
Authors: Luo Y, Liu L, Li LH, Deng QY
Article Title: Chiral Resolution of Racemic 4-Phenyl(benzyl)-2-Oxazolidone by Use of Molecularly Imprinted Polymers.
Publication date: 2007
Journal: Chromatographia
Volume: 65
Issue: (11)
Page numbers: 675-679.
DOI: 10.1365/s10337-007-0209-7

Abstract: Abstract: Polymers imprinted with (S)-4-phenyl-2-oxazolidone and (S)-4-benzyl-2-oxazolidone have been prepared by non-covalent imprinting. A combinational procedure was used to optimize the functional monomer and crosslinker. A copolymer of methacrylic acid and divinylbenzene resulted in the best chiral recognition. The ratio of template to functional monomer and solvent in the pre-polymerization mixture were also optimized. The imprinted polymers were used as stationary phases in high-performance liquid chromatography. The MIPs were more selective when prepared using a less polar solvent, except for toluene. Effective separations of the enantiomers of racemic 4-phenyl-2-oxazolidone and 4-benzyl-2-oxazolidone were achieved by use of acetonitrile as mobile phase; no cross-selectivity was observed. Interactions between functional monomers and template were investigated by 1H NMR spectroscopy. The results suggest that hydrogen-bonding between the functional monomer and the template and π - π stacking interaction between the cross-linker and the template may contribute to chiral recognition
Template and target information: (S)-4-phenyl-2-oxazolidone, (S)-4-benzyl-2-oxazolidone
Author keywords: column liquid chromatography, 1H NMR, Molecularly imprinted polymers, 4-Phenyl-2-oxazolidone

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