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EnglishThe 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".
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| Titolo: | The Hydrolysis of 4-Amino- and 4-Dimethylaminobenzene Sulfonyl Chlorides: An Unprecedented Case of Independence of Reactivity from pH |
| Autori: | |
| Data di pubblicazione: | 2011 |
| Rivista: | |
| 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". |
| Handle: | http://hdl.handle.net/11567/280020 |
| Appare nelle tipologie: | 01.01 - Articolo su rivista |
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