Kinetics and mechanism of large rate enhancement in an acidic aqueous cleavage of the tertiary amide bond of N-(2-methoxyphenyl)-N′-morpholinophthalamide (1)

被引：4
|
作者：
Sim, Yoke-Leng [1 ]
Ariffin, Azhar [1 ]
Khan, M. Niyaz [1 ]
机构：
[1] Univ Malaya, Dept Chem, Fac Sci, Kuala Lumpur 50603, Malaysia
来源：
BIOORGANIC CHEMISTRY | 2008年 / 36卷 / 4-6期
关键词：
N-(2-Methoxyphenyl)-N '-morpholinophthalamide; N-(2-Methoxyphenyl)phthalimide; Acidic hydrolysis; Kinetics; Intramolecular rate enhancement; Reaction mechanism;
D O I：
10.1016/j.bioorg.2008.03.003
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The rate of conversion of 1 to N-(2-methoxyphenyl)phthalimide (2) within [HCI] range 5.0 x 10(-3)-1.0 M at 1.0 M ionic strength (by NaCl) reveals the presence of both uncatalyzed and specific acid-catalyzed kinetic terms in the rate law. Intramolecular carboxamide group-assisted cleavage of amide bond of 1 reveals rate enhancement of much larger than 10(6)-fold compared to the expected rate of analogous intermolecular reaction. (C) 2008 Elsevier Inc. All rights reserved.
引用
收藏
页码：178 / 182
页数：5
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