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

Document Type

Article

Publication Date

1-1-2009

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

Keywords

Catalyzed amide hydrolysis, Aqueous-solution, General base, Rate enhancement, N-methyl, Formamide, State, Water, N, n-dimethylbenzamide, Methoxyaminolysis

Publication Title

International Journal of Chemical Kinetics

ISSN

0538-8066

Divisions

CHEMISTRY

Volume

41

Issue

1

Additional Information

Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA

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