Kinetics and Mechanism of Hydrolysis of N-(2'-Hydroxyphenyl)phthalamic Acid (1) and N-(2'-Methoxyphenyl)phthalamic Acid (2) in a highly alkaline medium

Ariffin, Azhar and Khan, M.N. and Sim, Y.L. and Damit, E.F. (2009) Kinetics and Mechanism of Hydrolysis of N-(2'-Hydroxyphenyl)phthalamic Acid (1) and N-(2'-Methoxyphenyl)phthalamic Acid (2) in a highly alkaline medium. International Journal of Chemical Kinetics, 41 (1). pp. 1-11. ISSN 0538-8066

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Abstract

A kinetic study on hydrolysis of N-(2'-hydroxyphenyl)phthalamic acid (1), N-(2'-methoxyphenyl)phthalamic acid (2), and N-(2'-methoxyphenyl)benzamide (3) under a highly alkaline medium gives second-order rate constants, k(OH), for the reactions of HO(-) with 1, 2, and 3 as (4.73 +/- 0.36) x 10(-8) at 35 degrees C, (2.42 +/- 0.28) x 10(-6) and (5.94 +/- 0.23) x 10(-5) M(-1) s(-1) at 65 degrees C, respectively. Similar values of k(OH) for 3, N-methylbenzanilide, N-methylbenzamide, and N,N-dimethylbenzamide despite the difference between pK(a) values of aniline and ammonia of similar to 10 pK units are qualitatively explained. (C) 2008 Wiley Periodicals, Inc, Int | Chem Kinet 41: 1-11, 2009

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: Catalyzed amide hydrolysis; Aqueous-solution; General base; Rate enhancement; N-methyl; Formamide; State; Water; N; n-dimethylbenzamide; Methoxyaminolysis
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 04:44
Last Modified: 27 Aug 2019 06:15
URI: http://eprints.um.edu.my/id/eprint/8081

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