✦ LIBER ✦

Kinetics and mechanism of tertiary amine-catalyzed cleavage of N′-morpholino-N-(2′-methoxyphenyl)phthalamide: Kinetic evidence for the presence of a reactive intermediate on the reaction path

✍ Scribed by Yoke-Leng Sim; M. Niyaz Khan

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 266 KB
Volume: 42
Category: Article
ISSN: 0538-8066
DOI: 10.1002/kin.20477

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✦ Synopsis

Abstract

Pseudo‐first‐order rate constants (k~obs~) for tertiary amine (DABCO and Me~3~N) buffer‐catalyzed cyclization of N′‐morpholino‐N‐(2′‐methoxyphenyl)phthalamide (1) to N‐(2′‐methoxyphenyl)phthalimide (2) reveal saturation (nonlinear) plots of k~obs~ versus [Buf]~T~ (total tertiary amine buffer concentration) at a constant pH. Such plots at different pH have been attributed to the presence of a reactive intermediate (T^−^) formed by tertiary amine buffer‐catalyzed intramolecular nucleophilic addition of the secondary amide nitrogen to the carbonyl carbon of the tertiary amide group of 1. © 2010 Wiley Periodicals, Inc. Int J Chem Kinet 42: 263–272, 2010

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## Abstract Kinetic study on the cleavage of __N__‐phenylphthalimide (NPhPT) in the presence of 0.05 M NH~2~NH~2~ and mixed H~2~O‐CH~3~CN solvents reveals the occurrence of reaction scheme equation image where A, B, C, C~1~, An, E, and F represent NPhPT, __o__‐CO^−^~2~C~6~H~4~CONHC~6~H~5~, __o__‐