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Acid‐catalyzed hydrolysis of 5‐substituted‐1 H ,3 H ‐2,1,3‐benzothiadiazole 2,2‐dioxides (5‐substituted benzosulfamides): kinetic behavior and mechanistic interpretations
Author(s) -
Gediz Erturk Aliye,
Bekdemir Yunus
Publication year - 2015
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.3419
Subject(s) - chemistry , hydrolysis , kinetic isotope effect , perchloric acid , sulfuric acid , substituent , catalysis , arrhenius equation , aqueous solution , acid catalysis , hydrochloric acid , deuterium , kinetic energy , medicinal chemistry , organic chemistry , activation energy , physics , quantum mechanics
The acid‐catalyzed hydrolysis of a series of 5‐substituted‐1 H ,3 H ‐2,1,3‐benzothiadiazole 2,2‐dioxides has been investigated in aqueous solutions of sulfuric, perchloric, and hydrochloric acid at 85.0 ± 0.05 °C. Analysis of the kinetic data by the excess acidity method, Arrhenius parameters, the order of the catalytic effects of strong acids, the kinetic deuterium isotope effect, and the substituent effect have indicated that the hydrolysis of 5‐substituted benzosulfamides 1a , 1b , 1c , 1d occur with a mechanistic switchover from A2 to A1 in the studied range: an A2 mechanism in low acidity regions and an A1 mechanism in high acid concentrations. Copyright © 2015 John Wiley & Sons, Ltd.