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.
|Number of pages
|Journal of the Chemical Society, Chemical Communications
|Published - 1 Dec 1979