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Please use this identifier to cite or link to this item: http://hdl.handle.net/123456789/18471

Title: Kinetics of the Alkaline Hydrolysis of Isatin and N-methylisatin in Water and Water-
Authors: F. Radman, Ramyah.
M. Ismail, Amel.
A. Al-Jallal, Nada.
Keywords: Alkaline hydrolysis; Isatin; Bond cleavage; Nucleophile; Pseudo-first-order kinetics; Thermodynamic activation parameters; Indole; Central nervous system; Entropy of activation
Issue Date: 2010
Publisher: Elsevier B.V.
Citation: JSCS, 14, 2, 223-229
Abstract: The kinetics of amide bond cleavage of isatin and N-methylisatin in the presence of N,N-dimethylacetamide (DMA) was followed spectrophotometrically in the range of solvent composition (0–48.53 wt.%) and temperatures (40–70 °C) using piperidine as a nucleophile. The reaction was studied under pseudo-first-order kinetics. The rate of the reaction decreases largely with increasing organic solvent content. The thermodynamic activation parameters were calculated and discussed in terms of solvation of the activated complex. No linearity was observed between log rate constant and the reciprocal dielectric constant for the solvent used suggesting that there is a selective solvation by higher polar solvent (water). Finally, a mechanism for the ring opening for isatin and N-methylisatin was proposed.
URI: http://hdl.handle.net/123456789/18471
ISSN: 1319-6103
Appears in Collections:College of Science

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