Solvent effects on the alkaline hydrolyses of 4-nitrophenyl N-aroyl-areneiminosulfonates

Kütük H., Tillett J. G.

Phosphorus, Sulfur and Silicon and Related Elements, vol.176, pp.95-109, 2001 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 176
  • Publication Date: 2001
  • Doi Number: 10.1080/10426500108055106
  • Journal Name: Phosphorus, Sulfur and Silicon and Related Elements
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.95-109
  • Keywords: Alkaline hydrolysis, Solvent effects, Sulfonimidic esters
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

Second-order rate constants have been determined for the alkaline hydrolyses of N-aroyl-p-toluenesulfonimidic esters in aqueous organic solvents. Rate minima were observed with decreasing water concentration in aqueous acetonitrile, dioxane and t-butanol mixtures whereas rates of hydrolysis decrease continuously in MeOH-H2O and increase in DMSO-H2O. Solvent effects, Arrhenius parameters, and substituent effects are consistent with either an addition-elimination or a concerted SN2-type mechanism.