Ariffin, Azhar and Khan, M.N. and Sim, Y.L. (2007) Kinetic evidence for the formation of monocationic N,N'-Disubstituted Phthalamide in tertiary Amine-Catalyzed hydrolysis of N-Substituted Phthalimides. Journal of Organic Chemistry, 72 (22). pp. 8452-8458. ISSN 0022-3263, DOI https://doi.org/10.1021/jo701295n.
Full text not available from this repository.Abstract
A kinetic study on the aqueous cleavage of N-(2-methoxyphenyl)phthalimide (1) and N-(2-hydroxyphenyl)-phthalimide (2), under the buffers of N-methylmorphohne, reveals the equilibrium presence of monocationic amide (Ctam) formed due to nucleophilic reactions of N-methylmorpholine with 1 and 2. Pseudo-first-order rate constants for the reactions of water and HO- with Ctam (formed through nucleophilic reaction of N-methylmorpholine with 1) are 4.60 x 10(-5) s(-1) and 47.9 M-1 s(-1), respectively. But the cleavage of Ctam, formed through nucleophilic reaction of N-methylmorpholine with 2, involves intramolecular general base (2(')-0(-) group of Ctam)-assisted water attack at carbonyl carbon of cationic amide group of Ctam in or before the rate-determining step.
| Item Type: | Article |
|---|---|
| Funders: | UNSPECIFIED |
| Additional Information: | Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA |
| Uncontrolled Keywords: | Amines/*chemistry; Catalysis; Cations/chemical synthesis/chemistry; Hydrolysis; Kinetics; Molecular Structure; Phthalimides/*chemical synthesis/chemistry; Water/chemistry |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Miss Malisa Diana |
| Date Deposited: | 03 Jul 2013 08:40 |
| Last Modified: | 27 Aug 2019 06:13 |
| URI: | http://eprints.um.edu.my/id/eprint/8052 |
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