Effects of mixed Aqueous-Organic solveuts on the rate of intramolecular Carboxylic Group-Catalyzed cleavage Of N-(4'-Methoxyphenyl)-Phthalamic Acid

Ariffin, A. and Khan, M.N. and Leng, S.Y. (2004) Effects of mixed Aqueous-Organic solveuts on the rate of intramolecular Carboxylic Group-Catalyzed cleavage Of N-(4'-Methoxyphenyl)-Phthalamic Acid. International Journal of Chemical Kinetics, 36 (6). pp. 316-325. ISSN 0538-8066

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Abstract

Kinetic study on the cleavage of N-(4'-methoxyphenyl)phthalamic acid (NMPPAH) in mixed H2O-CH3CN and H2O-1,4-dioxan solvents containing 0.05 M HCl reveals the formation of phthalic anhydride (PAn)/phthalic acid (PA) as the sole or major product. Pseudo first-order rate constants (k(1)) for the conversion of NMPPAH to PAn decrease nonlinearly from 60.4 x 10(-5) to 2.64 x 10(-5) s(-1) with the increase in the contents of 1,4-dioxan from 10 to 80% v/v in mixed aqueous solvents. The rate of cleavage of NMPPAH in mixed H2OCH3CN solvents at greater than or equal to 50% v/v CH3CN follows an irreversible consecutive reaction path: NMPPAH k(1) --> PAn k(2) --> PA. The values of k(1) are larger in H2O-CH3CN than in H2O-1,4-dioxan solvents. (C) 2004 Wiley Periodicals, Inc.

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: N-substituted phthalimides; Alkaline-hydrolysis; Amide hydrolysis; Phthalamic acid; Imide formation; Primary amines; Mechanism; Kinetics; Derivatives; Anhydride
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 09:15
Last Modified: 03 Jul 2013 09:15
URI: http://eprints.um.edu.my/id/eprint/8042

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