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Investigation of the acid‐catalyzed hydrolysis and reaction mechanisms of N , N ′‐diarylsulfamides using various criteria
Author(s) -
Bekdemir Yunus,
Gediz Erturk Aliye,
Kutuk Halil
Publication year - 2014
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3242
Subject(s) - chemistry , hydrolysis , catalysis , mineral acid , reaction mechanism , kinetic isotope effect , mechanism (biology) , solvent , aqueous solution , kinetic energy , organic chemistry , medicinal chemistry , philosophy , physics , epistemology , deuterium , quantum mechanics
The mechanism of acid‐catalyzed hydrolysis of a series of p ‐substituted N , N ′‐diarylsulfamides 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 © 2013 John Wiley & Sons, Ltd.