title: The hydrolysis of 4-amino- and 4-dimethylaminobenzene sulfonyl chlorides: an unprecedented case of independence of reactivity from pH.
abstract: The reactivity-pH profile for the hydrolysis of 4-aminobenzenesulfonyl chloride 1 has a sigmoid shape with a plateau extending from pH 2 to 11; reactivity of N,N-dimethyaminobenzenesulfonyl chloride 4 is invariant over an even wider pH range (0-14.7). These results, together with the activation data determined at selected pH's for compound 1, are interpreted in light of the occurrence of a reaction mechanism that is dissociative in nature, in which nucleophilic assistance by solvent molecules is given to the amino group of 1 acting as an "internal nucleophile".
authors.affiliation: Department of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso, 31-16146 Genova, Italy. giorgio.cevasco@unige.it
authors.forename: Giorgio
authors.initials: G
authors.lastname: Cevasco
authors.forename: Anna
authors.initials: A
authors.lastname: Piatek
authors.forename: Sergio
authors.initials: S
authors.lastname: Thea