B. Chankvetadze, L. Chankvetadze, S. Sidamonidze
Nov 7, 1997
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1
Influential Citations
116
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Journal
Journal of Chromatography A
Abstract
3-Fluoro-, 3-chloro- and 3-bromo-5-methylphenylcarbamates of cellulose and amylose were prepared and their chiral recognition abilities as chiral stationary phases for high-performance liquid chromatography (HPLC) were evaluated and compared with those of the 3,5-difluoro-, 3,5-dichloro- and 3,5-dimethylphenylcarbamates of cellulose and amylose. The introduction of both an electron-donating methyl group and an electron-withdrawing halogen group onto the phenyl moieties markedly modified the polarities of the carbamate residues. Among the cellulose derivatives, cellulose tris(3-fluoro-5-methylphenylcarbamate) showed an excellent chiral recognition ability and resolved some racemates better than the corresponding 3,5-difluoro- and 3,5-dimethylphenylcarbamates of cellulose. The amylose derivatives exhibited a characteristic chiral recognition depending on the substituents. The effects of substituents on chiral discrimination is discussed on the basis of enantioseparation results in HPLC, IR, 1H NMR and circular dichroism (CD) data. Some chiral drugs were better resolved on cellulose tris(3-chloro-5-methylphenylcarbamate) than cellulose tris(3,5-dimethylphenylcarbamate).