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Stepwise proton transfer trapping

BASE CATALYSIS (nucleophile with labile proton) [Pg.303]

An example of a proton-transfer reaction occurring by the stepwise trapping mechanism (Ch. 7, Section 2.1) is the general base-catalysed aminolysis of benzyl-penicillin. Amines react with penicillin to form an unstable tetrahedral intermediate which may be trapped by a diffusion-controlled encounter with a strong base as shown in Eqn. 8. Diamines also undergo this reaction but at a much faster rate than monoamines of the same basicity which is attributed to intramolecular general base catalysis i.e. the second amino group acts as a proton acceptor (V). However, the effect of intramolecularity itself is small and the effective concentration (Ch. 1)... [Pg.238]

See other pages where Stepwise proton transfer trapping is mentioned: [Pg.302]    [Pg.231]    [Pg.231]    [Pg.302]    [Pg.231]    [Pg.231]    [Pg.975]    [Pg.310]    [Pg.385]    [Pg.83]    [Pg.273]   


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