Kinetics and mechanism of the formation of methacrylamide from 2-methyl-2-sulphatopropionamide in strong acid media

Abstract

The kinetics and mechanism of the elimination of sulphuric acid from the sulphate ester of 2-hydroxy-2-methylpropionamide in 90–102% H₂SO₄ have been studied by multinuclear (¹H, ²H, ¹³C and ¹⁵N) NMR spectroscopy. The results, which include activation parameters, influence of acid strength and kinetic isotope effects, are consistent with an E₂ elimination occurring from the protonated substrate and involving the hydrogensulphate anion as a base.