A Kinetic Study of Acid-Catalyzed Hydrolysis of Some Arylsulfonyl Phthalimides

Kütük H., Öztürk S.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.184, no.2, pp.332-340, 2009 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 184 Issue: 2
  • Publication Date: 2009
  • Doi Number: 10.1080/10426500802119655
  • Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED)
  • Page Numbers: pp.332-340
  • Keywords: Acid-catalyzed hydrolysis, arylsulfonyl phthalimides, excess acidity, mechanism, EXCESS ACIDITIES, MECHANISMS, PROTONATION
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The acid-catalyzed hydrolysis of arylsulfonyl phthalimides was studied in aqueous solutions of sulfuric, perchloric, and hydrochloric acid at 35.0 0.1C. Analysis of the data by the excess acidity method and activation parameters, as well as substituent and solvent isotope effects, indicate hydrolysis by an A-2 mechanism at low acidity. At higher acidities, a changeover to an A-1 mechanism is observed.