ALKALINE HYDROLYSIS OF BENZAMIDE AND N-METHYL- AND N,N-DIMETHYLBENZAMIDE

被引：74

作者：

BUNTON, CA

NAYAK, B

OCONNER, C

机构：

[1] Department of Chemistry, University of California at Santa Barbara, Santa Barbara, California

[2] William Ramsay and Ralph Forster Laboratorie, University College, London

[3] Department of Chemistry, University of Auckland, Auckland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1968年 / 33卷 / 02期

关键词：

D O I：

10.1021/jo01266a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alkaline hydrolyses of benzamideand N-methylbenzamide, but not of N,N-dimethylbenzamide, are accompaniedby extensive oxygen exchange betweenwater and the amide. The values ofk0/kh for benzamide decrease with increasing hydroxide ion concentration and are greaterin deuterium than in protium oxide. For hydrolysis of benzamide, kH2O/kD2O is 1.4, andfor N,N-dimethylbenzamide it is 0.88. These differences arise because of the solvent isotope effect upon partitioning of the tetrahedral intermediate derived from benzamide. © 1968, American Chemical Society. All rights reserved.

引用

页码：572 / &

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