SPONTANEOUS RACEMIZATION OF CHLORTHALIDONE - KINETICS AND ACTIVATION PARAMETERS

被引：15

作者：

SEVERIN, G

机构：

[1] Bolar Pharmaceutical Co, Inc., Copiague, New York

来源：

CHIRALITY | 1992年 / 4卷 / 04期

关键词：

3-HYDROXY-3-PHENYLPHTHALIMIDINES; INVERSION (OF CONFIGURATION); BARRIER TO INVERSION; RATE CONSTANTS (OF INVERSION); ENANTIOMER INTERCONVERSION; CARBONIUM ION (INTERMEDIATE IN RACEMIZATION);

D O I：

10.1002/chir.530040404

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The enantiomers of chlorthalidone (CTD) and a minor, achiral dehydration product, DELTA-2-CTD, are shown to exist in dynamic equilibrium in aqueous media through a carbonium ion intermediate. The barrier to inversion at carbon is low for an uncatalyzed system: DELTA-G double dagger = 21.6 kcal/mol. This behavior extends to other 3-hydroxy-3-phenylphthalimidines (HPPs), with formation of the analogous DELTA-2-HPP blocked by alkyl substitution at the 2-nitrogen.

引用

页码：222 / 226

页数：5

共 6 条

[1] CARBONIUM-IONS IN SOLUTION .9. RELATIONSHIP BETWEEN CARBOCATIONS IN SUPERACID AND SOLVOLYSIS TRANSITION-STATES [J].