Kinetic evidence for the formation of monocationic N,N'-Disubstituted Phthalamide in tertiary Amine-Catalyzed hydrolysis of N-Substituted Phthalimides

Ariffin, A. and Khan, M.N. and Sim, Y.L. (2007) Kinetic evidence for the formation of monocationic N,N'-Disubstituted Phthalamide in tertiary Amine-Catalyzed hydrolysis of N-Substituted Phthalimides. Journal of Organic Chemistry, 72 (22). pp. 8452-8458. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/pdfplus/10.1021/jo701295n

Abstract

A kinetic study on the aqueous cleavage of N-(2-methoxyphenyl)phthalimide (1) and N-(2-hydroxyphenyl)-phthalimide (2), under the buffers of N-methylmorphohne, reveals the equilibrium presence of monocationic amide (Ctam) formed due to nucleophilic reactions of N-methylmorpholine with 1 and 2. Pseudo-first-order rate constants for the reactions of water and HO- with Ctam (formed through nucleophilic reaction of N-methylmorpholine with 1) are 4.60 x 10(-5) s(-1) and 47.9 M-1 s(-1), respectively. But the cleavage of Ctam, formed through nucleophilic reaction of N-methylmorpholine with 2, involves intramolecular general base (2(')-0(-) group of Ctam)-assisted water attack at carbonyl carbon of cationic amide group of Ctam in or before the rate-determining step.

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: Amines/*chemistry; Catalysis; Cations/chemical synthesis/chemistry; Hydrolysis; Kinetics; Molecular Structure; Phthalimides/*chemical synthesis/chemistry; Water/chemistry
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 08:40
Last Modified: 03 Jul 2013 08:40
URI: http://eprints.um.edu.my/id/eprint/8052

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