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

页码：178 / 182

页数：5

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