Kinetics and mechanism of hydrolysis of N‐(2′‐hydroxyphenyl)phthalamic acid (1) and N‐(2′‐methoxyphenyl)phthalamic Acid (2) in a highly alkaline medium |
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| Authors: | Yoke‐Leng Sim Emmy Fadhiza Damit Azhar Ariffin M Niyaz Khan |
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| Institution: | Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia |
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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, kOH, 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 kOH for 3 , N‐methylbenzanilide, N‐methylbenzamide, and N,N‐dimethylbenzamide despite the difference between pKa 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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