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 -side in disagreement with the prediction of the theory of stereoelectronic control
Intramolecular general acid catalysis in the aminolysis of benzylpenicillin. A preferred direction of nucleophilic attack
Martin, Anthony F., Morris, Jeffrey J. and Page, Michael I.
(1979)
Intramolecular general acid catalysis in the aminolysis of benzylpenicillin. A preferred direction of nucleophilic attack.
Chemical Communications (6).
pp. 298-299.
ISSN 1359-7345
CORE (COnnecting REpositories)
CORE (COnnecting REpositories)
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