Kinetics and mechanism of large rate enhancement in an Acidic Aqueous Cleavage of the Tertiary Amide Bond of N-(2-Methoxyphenyl)-N'-Morpholinophthalamide (1)

Ariffin, A. and Khan, M.N. and Sim, Y.L. (2008) Kinetics and mechanism of large rate enhancement in an Acidic Aqueous Cleavage of the Tertiary Amide Bond of N-(2-Methoxyphenyl)-N'-Morpholinophthalamide (1). Bioorganic Chemistry, 36 (4-6). pp. 178-182. ISSN 0045-2068

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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.

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: Acids/*chemistry; Hydrogen-Ion Concentration; Kinetics; Molecular Structure; Morpholines/chemical synthesis/*chemistry; Phthalic Acids/chemical synthesis/*chemistry; Temperature
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 07:01
Last Modified: 03 Jul 2013 07:01
URI: http://eprints.um.edu.my/id/eprint/8066

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