Journal of the Chemical Society. Perkin transactions II p. 117 - 122 (1986)
Update date:2022-08-11
Topics:
Castro, Albino
Leis, J. Ramon
Pena, M. Elena
Tato, Jose Vazquez
The hydrolysis of N-nitroso-2-imidazolidone has been studied kinetically between pH 8.3 and 12.6.This nitroso compound has an acid-base equilibrium whose constant has been determined spectrophotometrically (pKa 11.45).Only the acid form is reactive.At pH < 10 hydrolysis is of order less than one with respect to OH- and is subject to general base catalysis.These results are interpreted in terms of a mechanism involving an initial steady-state hydrate whose decomposition by base leads to the final products.At pH > 10 reaction paths of orders one and two in OH- appear.The second-order term reflects general base catalysis superimposed on a first-order term in OH- (the bases dimethylamine, sarcosine, piperidine, and HPO42- have been used).The results are interpreted by an initial OH- attack on the carbonyl group of the nitroso compound to give an intermediate which in the rate-controlling step reacts with bases, among them water (which explains the first-order term with respect to OH-).The low value of the Broensted relation (β ca.O) and the fact that the intermediate possesses no proton yielding a low pKa value suggest that there is inverse classical general base catalysis.
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