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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