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- W2068593734 abstract "The rate of aminolysis of benzylpenicillin and cephaloridine by hydroxylamine, unlike other amines, shows only a first order dependence on amine concentration. The rate enhancement compared with that predicted from a Bronsted plot for other primary amines with benzylpenicillin is greater than 10(6). This is much more than an alpha-effect and is compatible with rate-limiting formation of the tetrahedral intermediate due to a rapid intramolecular general acid catalysed breakdown of the intermediate. For cephaloridine, the rate enhancement is greater than 10(4) which demonstrates that beta-lactam C-N bond fission and expulsion of the leaving group at C3' are not concerted." @default.
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- W2068593734 date "2004-01-01" @default.
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- W2068593734 title "Intramolecular general acid catalysis in the aminolysis of β-lactam antibiotics" @default.
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- W2068593734 doi "https://doi.org/10.1039/b313900j" @default.
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