Issue 6, 1976

General-base-catalysed proton exchange in 1,3-dimethyl-2-iminoimidazolidin-4-one hydriodide

Abstract

The general-base-catalysed exchange of the methylene protons of the title compound in D2O has been studied using n.m.r. techniques with 70 bases that include aliphatic monocarboxylates and dicarboxylates, o-, m-, and p-substituted benzoates, 2-, 3-, and 4-substituted pyridines, creatinine, and D2O. Aliphatic monocarboxylates, m- and p-substituted benzoates, the pyridines, and D2O conform to a single Brønsted relationship (β 0.79 ± 0.05). However, o-substituted benzoates exhibit enhanced catalytic activity while the aliphatic dicarboxylates and creatinine show reduced catalytic activity. The possible causes for such deviations are discussed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1976, 674-679

General-base-catalysed proton exchange in 1,3-dimethyl-2-iminoimidazolidin-4-one hydriodide

R. Srinivasan and R. Stewart, J. Chem. Soc., Perkin Trans. 2, 1976, 674 DOI: 10.1039/P29760000674

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