The Journal of organic chemistry

Kinetics and Mechanism of Large Rate Enhancement in the Alkaline Hydrolysis of N′-Morpholino-N-(2′-methoxyphenyl) phthalamide

YL Sim, A Ariffin, MN Khan

Index: Sim, Yoke-Leng; Ariffin, Azhar; Khan, M. Niyaz Journal of Organic Chemistry, 2008 , vol. 73, # 10 p. 3730 - 3737

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Citation Number: 9

Abstract

The apparent second-order rate constant (k OH) for hydroxide-ion-catalyzed conversion of 1 to N-(2′-methoxyphenyl) phthalamate (4) is∼ 103-fold larger than k OH for alkaline hydrolysis of N-morpholinobenzamide (2). These results are explained in terms of the reaction scheme 1→ k 1 obs 3→ k 2 obs 4 where 3 represents N-(2′-methoxyphenyl) phthalimide and the values of k 2obs/k 1obs vary from 6.0× 102 to 17× 102 within [NaOH] ...