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Kinetics and mechanism of hydrolysis of N-(2′-hydroxyphenyl)phthalamic acid (1) and N-(2′-methoxyphenyl)phthalamic Acid (2) in a highly alkaline medium

✍ Scribed by Yoke-Leng Sim; Emmy Fadhiza Damit; Azhar Ariffin; M. Niyaz Khan

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
160 KB
Volume
41
Category
Article
ISSN
0538-8066

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✦ Synopsis

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) × 10^−8^ at 35°C, (2.42 ± 0.28) × 10^−6^ and (5.94 ± 0.23) × 10^−5^ M^−1^ s^−1^ at 65°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 ∼10 pK units are qualitatively explained. © 2008 Wiley Periodicals, Inc. Int J Chem Kinet 41: 1–11, 2009

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