Intramolecular general acid catalysis in the aminolysis of benzylpenicillin. A preferred direction of nucleophilic attack
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 6,p. 298-299
- https://doi.org/10.1039/c39790000298
Abstract
The reaction of 1,2-diaminoethane monocation with benzylpenicillin shows a rate enhancement of ca. 100-fold compared with a monoamine of similar basicity; this is attributed to intramolecular general acid catalysis which in turn indicates that nucleophilic attack takes place from the least hindered α-side in disagreement with the prediction of the theory of stereoelectronic control.This publication has 1 reference indexed in Scilit:
- Intra-and inter-molecular general base catalysis in the aminolysis of benzylpenicillinJournal of the Chemical Society, Chemical Communications, 1976