The Kinetic Study On The Effects Of Mixed Aqueous-Organic Solvents On The Rate Of O- And N- Cyclisation Of N-(4 '-Nitrophenyl)Phthalamic Acid

Ariffin, A. and Khan, M.N. and Ahmad, W.H.W. (2007) The Kinetic Study On The Effects Of Mixed Aqueous-Organic Solvents On The Rate Of O- And N- Cyclisation Of N-(4 '-Nitrophenyl)Phthalamic Acid. Indian Journal of Chemistry Section a-Inorganic Bio-Inorganic Physical Theoretical & Analytical Chemistry, 46 (3). pp. 416-461. ISSN 0376-4710

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Abstract

The pseudo-first-order rate constants (k(obs)) for the intramolecular carboxylic group-assisted cleavage of N-(4'-nitrophenyl)phthalamic acid (1) show nonlinear decrease of similar to 17-fold and similar to 117-fold with the increase in the respective contents of CH3CN (10-80% v/v) and 1,4-dioxan (9.5-79.4% v/v) in mixed aqueous solvents. The fraction of N-cyclization of 1 leading to the formation of N-(4'-nitrophenyl)phthalimide, 2, remains almost zero at <= 40% v/v CH3CN while it increases from 0.06 to 0.49 with increase in CH3CN content (50-80% v/v) at 1.0 x 10(-3) M HCl. However, the observed data reveal an almost absence of N-cyclization within 1,4-dioxan content range 10-80% v/v.

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: intramolecular catalysis, amide hydrolysis, phthalanilic acids, phthalic-anhydride, base catalysis, participation, mechanism, cleavage
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 09:02
Last Modified: 03 Jul 2013 09:02
URI: http://eprints.um.edu.my/id/eprint/8049

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