Chiral recognition of phenylacetic acid derivatives by aminated cyclodextrins

被引：38

作者：

Kitae, T ^{[1
]}

Takashima, H ^{[1
]}

Kano, K ^{[1
]}

机构：

[1] Doshisha Univ, Fac Engn, Dept Mol Sci & Technol, Kyoto 61003, Japan

来源：

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY | 1999年 / 33卷 / 03期

关键词：

chiral recognition; phenylacetic acid derivatives; aminated cyclodextrins; capillary zone; electrophoresis; H-1; NMR;

D O I：

10.1023/A:1008090113212

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral recognition of mandelic acid (1), acetylmandelic acid (2), 1-methoxyphenyl acetic acid (3), phenylsuccinic acid (4), 2-phenylpropanoic acid (5) and ibuprofen (6) in their anionic forms by protonated 6(A)-amino-6(A)-deoxy-beta-cyclodextrin (mono-NH3+-beta-CD) and 6(A),6(D)-diamino-6(A),6(D)-dideoxy-beta-cyclodextrin (di-NH3+-beta-CD) has been studied by means of capillary zone electrophoresis (CZE) and H-1 NMR spectroscopy. Both methods show the preferable guests for mono-NH3+-beta-CD to be the (R)-enantiomers of 1, 3 and 5 and the (S)-enantiomers of 2, 4 and 6. Cooperative work of Coulomb interactions and inclusion is essential for chiral recognition of these anionic guests.

引用

页码：345 / 359

页数：15

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