Investigation of the acid-catalyzed hydrolysis and reaction mechanisms of N,N '-diarylsulfamides using various criteria

Bekdemir Y., ERTÜRK A. G., Kütük H.

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, vol.27, no.2, pp.94-98, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 2
  • Publication Date: 2014
  • Doi Number: 10.1002/poc.3242
  • Journal Name: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.94-98
  • Keywords: acid catalysis, diarylsulfamides, excess acidity, hydrolysis, mechanism, DEUTERIUM OXIDE, EXCESS ACIDITY, ESTER HYDROLYSIS, REACTION-RATES, SULFURIC-ACID, KINETICS, PROTONATION, DERIVATIVES, MIXTURES, WATER
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The mechanism of acidaEurocatalyzed hydrolysis of a series of paEurosubstituted N,NaEuro(2)aEurodiarylsulfamides was investigated in aqueous mineral acid solutions. Rate profiles, reaction activation parameters, catalytic order of strong acids, solvent isotope effects, and analysis of the kinetic data by the excess acidity method suggest a change in the mechanism from A2 to A1. While the hydrolysis proceeds with an A2 mechanism in low acidity regions, an A1 mechanism takes place in high acid concentrations. Copyright a (c) 2013 John Wiley & Sons, Ltd.