The reactivity-pH profile for the hydrolysis of 4-aminobenzenesulfonyl chloride 1 has a sigmoid shape with a plateau extending from pH 2 to pH 11; reactivity of N,N-dimethyaminobenzenesulfonyl chloride 4 is invariant over an even wider pH range (0 to 14.7). These results, together with the activation data determined at selected pHs 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 internal nucleophile.
The hydrolysis of 4-amino- and 4-dimethylaminobenzene sulfonyl chlorides: an unprecedented case of independence of reactivity from pH
Giorgio Cevasco;
2011
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 pH 11; reactivity of N,N-dimethyaminobenzenesulfonyl chloride 4 is invariant over an even wider pH range (0 to 14.7). These results, together with the activation data determined at selected pHs 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 internal nucleophile.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
