Effects of Mixed H2O-CH3CN solvents on the rate of Hydrazinolysis of N-Phenylphthalimide: spectral and kinetic evidence for The occurrence Of N-Aminophthalimide on the reaction path

Ariffin, A. and Khan, M.N. and Lan, L.C. and Leng, S.Y. (2005) Effects of Mixed H2O-CH3CN solvents on the rate of Hydrazinolysis of N-Phenylphthalimide: spectral and kinetic evidence for The occurrence Of N-Aminophthalimide on the reaction path. International Journal of Chemical Kinetics, 37 (3). pp. 147-161. ISSN 0538-8066

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Abstract

Kinetic study on the cleavage of N-phenylphthalimide (NphPT) in the presence of 0.05 M NH2NH2 and mixed H2O-CH3CN solvents reveals the occurrence of reaction scheme GRAPHICS where A, B, C, C-1, An, E, and F represent NPhPT, o-CO2-C6H4CONHC6H5, o-CONHNH2C6H4-CONHC6H5, N-aminophthalimide, aniline, o-CO2-C6H4CONHNH2, and o-CONHNH2C6H4-CONHNH2, respectively. But, in the presence of either nonbuffered greater than or equal to -0.20 M NH2NH2 or hydrazine buffer of pH similar to 7.30-8.26 with total buffer concentration (\Buf\(T)) of >0.02 M, further conversion of Fto 2,3-dihydrophthalazine-1,4-dione(DHPD) has been detected depending upon the length of the reaction time (t), the values of \Buf\(T), and pH. It has been shown that the rate of conversion of C, to F is much faster than that of C to C, which is much faster than that of F to DHPD. The reaction step A --> C involves general base (GB) catalysis, while step C --> C-1 seems to involve specific base-general acid (GA) and GB-GB catalysis. (C) 2005 Wiley Periodicals, Inc.

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: acid-base catalysis, intramolecular aminolysis, nucleophilic-attack, mechanism, phthalimide, cyclization, cleavage, buffers, esters, amides
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 09:05
Last Modified: 20 Oct 2014 05:44
URI: http://eprints.um.edu.my/id/eprint/8045

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