Kinetics and mechanism of isatin ring opening in aqueous binary mixtures of methanol and acetonitrile cosolvents
✍ Scribed by A. M. Ismail; A. A. Zaghloul
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 162 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0538-8066
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✦ Synopsis
Solvent effects on the kinetics of hydrolysis of isatin by sodium hydroxide have been investigated within the temperature range (30-55ЊC) in methanol-water and acetonitrilewater media of varying solvent compositions up to 70% (v/v) of the organic solvent component. The thermodynamic activation parameters were calculated and discussed in terms of solvation effects. The determined isokinetic temperatures, in both systems, revealed the existence of compensation effect arising from strong solute-solvent interactions; log k was correlated with both log [H 2 O] and the reciprocal of the dielectric constant. The first correlation was observed to be linear while the second was nonlinear. Finally a mechanism for the isatin ring opening was proposed, which accounts for the role and the effect of the solvent on the reaction rate.