Abstract
Malonic acid, methylmalonic acid, ethylmalonic acid and phenylmalonic acid react with electrophilic nitrosating agents and also with bromine and iodine via their corresponding enol or enolate forms. In most cases it is possible to make either the enolisation or reaction of the enol rate-limiting by a suitable choice of reactant concentrations and reactivity. The enolisation rate constants agree reasonably well with literature values where they exist. We propose minimum figures of 1.0 × 10 −8 and 1.6 × 10 −8 respectively for K E the enolisation equilibrium constant for malonic acid and methylmalonic acid. The kinetic term second order in [malonic acid] or its derivatives (when enolisation is rate limiting) has been shown to arise from a base catalysed component to the reaction brought about by the malonate ion, which dominates at pH values greater than ca. 3.
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