e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521
Intramolecularly catalyzed sulfonamide hydrolysis. 8. Intramolecular nucleophilic catalysis by a neighboring hydroxyl group in acid-catalyzed benzenesulfonamide …
A Wagenaar, AJ Kirby…
Index: Wagenaar, Anno; Kirby, Anthony J.; Engberts, Jan B. F. N. Journal of Organic Chemistry, 1984 , vol. 49, # 19 p. 3445 - 3448
Me Me Me2NH2+ H20 molarity of the neighboring hydroxyl group of lb is far greater than that of solvent water. The rate constants for hydrolysis of lb and 2b show almost identical dependencies on acid concentration6 (1 b,+ 1.14, r2= 1.00). The small inverse solvent deuterium isotope effect for the reaction of 2b (kHzO/kDzO= 0.84 in 0.05 M aqueous HC1 at 25.50 OC) is also consistent with specific acid catalysis of the intramolecular reaction. The ...
