97042-35-8Relevant academic research and scientific papers
Catalysis of Sulfonate Ester Hydrolysis by Intramolecular Amide Group Assistance.
Thea, Sergio,Guanti, Giuseppe,Hopkins, Andrew R.,Williams, Andrew
, p. 3336 - 3341 (2007/10/02)
Kinetics of the alkaline hydrolysis of aryl 2-(acylamino)benzenesulfonates (1, X=OAr) obey the equation kobs=(Ka+kb->/(1++>/Ko).Hammett equations correlate the parameters ka, kb, and Ka for variation in both amido and leaving phenolate substituents.The values and sign of the ρ values together with entropy of activation data, reactivity trapping, and oxygen-18 incorporation are consistent with the formation of an intermediate benzoxathiazine S,S-dioxide (2).The ka term involves intramolecular attack of the amido anion.The kb term is consistent with a specific anion effect on ka.Regular bimolecular BAc2 mechanisms for ka and kb are not consistent with the high observed reactivity of these parameters.
