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PRESSURE EFFECT AND MECHANISM IN ACID CATALYSIS: VIII. HYDROLYSIS OF ACETAMIDE AND BENZAMIDE

 

作者: A. R. Osborn,   T. C-W. Mak,   E. Whalley,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1961)
卷期: Volume 39, issue 5  

页码: 1101-1108

 

ISSN:0008-4042

 

年代: 1961

 

DOI:10.1139/v61-137

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

The effect of pressures up to 3 kbar on the rate of the acid-catalyzed hydrolysis of acetamide and benzamide in both dilute and concentrated perchloric acid has been measured. The volumes of activation in dilute acid are consistent with a transition state that is not highly polar. It follows from this that if the attacking water molecule adds to the amidium ion then the reactive amidium ion is the O-protonated form, and if the attacking water molecule substitutes then the reactive amidium ion is the N-protonated form.The volume of activation for acetamide in concentrated acid provides no additional information about the mechanism. That for benzamide in concentrated acid is tentatively interpreted as favoring the O-protonated benzamidium ion as the reactive ion.

 

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