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Abstract
Kinetic and equilibrium solvent isotope effects have been measured for proton transfer from 4-(3-nitrophenylazo)salicylate ion (HA) to general bases (B) to examine whether a primary kinetic isotope effect is observed when proton transfer is occurring between bases of roughly equal strength for which ΔpK= pKHA– pKBH+= 0. The kinetic solvent isotope effects for catalysis by three tertiary amines (ΔpK–0.85, –0.27, and + 0.58) are kBH2O/kBD2O 2.0 ± 0.3, 2.2 ± 0.3, and 1.7 ± 0.2. Since for proton transfer to hydroxide ion (ΔpK–5.0) the observed isotope effect has a value kOH–H2O/kOD–D2O of 1.5 ± 0.1, the primary isotope effect for these proton transfers must be small and independent of base strength over the range studied. An explanation in terms of the reaction mechanism is given.
Published Version
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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