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 |
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Authors: | Yoke‐Leng Sim M. Niyaz Khan |
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Affiliation: | Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia |
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Abstract: | Pseudo‐first‐order rate constants (kobs) for tertiary amine (DABCO and Me3N) buffer‐catalyzed cyclization of N′‐morpholino‐N‐(2′‐methoxyphenyl)phthalamide ( 1 ) to N‐(2′‐methoxyphenyl)phthalimide ( 2 ) reveal saturation (nonlinear) plots of kobs 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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