THE MECHANISMS OF ACID-CATALYZED HYDROLYSIS OF N-(4-SUBSTITUTED ARYLTHIO) PHTHALIMIDES

Kütük H., Yakan H.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.186, no.7, pp.1460-1469, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 186 Issue: 7
  • Publication Date: 2011
  • Doi Number: 10.1080/10426507.2010.517584
  • Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1460-1469
  • Keywords: Acid-catalyzed hydrolysis, arylthiophthalimides, excess acidity, sulfenimides, EXCESS ACIDITIES, PROTONATION, KINETICS, SULFUR
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The acid-catalyzed hydrolysis of N-(4-substitutedarylthio)phthalimides was studied in aqueous solutions of sulfuric, perchloric, and hydrochloric acids at 40.0 +/- 0.1 degrees C. Analysis of the data by the excess acidity method, activation parameters, and substituent effects indicates hydrolysis by an A-2 mechanism at low acidity. At higher acidities, a changeover to an A-1 mechanism is observed.