Kinetics and mechanisms of the acid-catalyzed hydrolyses of N-(4-substitued-arylsulfinyl)phthalimides

Kütük H., Bekdemir Y., Soydas Y.

Journal of Physical Organic Chemistry, vol.14, no.4, pp.224-228, 2001 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 14 Issue: 4
  • Publication Date: 2001
  • Doi Number: 10.1002/poc.353
  • Journal Name: Journal of Physical Organic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.224-228
  • Keywords: Acid catalysis, Excess acidity, Hydrolysis, Mechanism, N-(4-substituted-arylsulfinyl)phthalimides
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The acid-catalyzed hydrolyses of N-(4-substituted-arylsulfinyl)phthalimides were studied in aqueous solutions of perchloric and sulfuric acids at 50.0 ± 0.1 and of hydrochloric acid at 40.0 ± 0.1°C. Analysis of the data by the Cox-Yates excess acidity method and substituent, temperature and solvent isotope effects indicate hydrolysis by an A2 mechanism at low acidity. At higher acidities a changeover to an A1 mechanism is observed. Copyright © 2001 John Wiley & Sons, Ltd.