Kinetics and mechanism of large rate enhancement in an Acidic Aqueous Cleavage of the Tertiary Amide Bond of N-(2-Methoxyphenyl)-N'-Morpholinophthalamide (1)
Document Type
Article
Publication Date
1-1-2008
Abstract
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.
Keywords
Acids/*chemistry, Hydrogen-Ion Concentration, Kinetics, Molecular Structure, Morpholines/chemical synthesis/*chemistry, Phthalic Acids/chemical synthesis/*chemistry, Temperature
Divisions
CHEMISTRY
Publication Title
Bioorganic Chemistry
Volume
36
Issue
4-6
Additional Information
Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA