Journal of the American Chemical Society p. 3220 - 3226 (1983)
Update date:2022-08-17
Topics:
Okuyama, Tadashi
Kawao, Shoji
Fueno, Takayuki
Acid-catalyzed hydrolysis of 1,1-bis(methylthio)ethene has been studied kinetically in 10percent aqueous acetonitrile at 30 deg C.The rate increased with buffer concentration, showing saturation at higher concentrations.Addition of 2-mercaptoethanol had little influence on the rate at the limiting zero buffer concentration, but it greatly accelerated the reaction in buffer solutions and followed a saturation curve.It was concluded that the rate-determining step is largely the protonation of the double bond at zero buffer concentration (k2/k-1 = 3.13) but it changes to the attack of water on the intermediate carbenium ion as the buffer concentration increases.The 1H NMR spectral analysis of the reaction products in 80percent CH3CN-D2O showed that the H-D isotope exchange at the 2-position of the substrate occurred extensively in a formate buffer but only moderatly in a DCl solution during the hydrolysis.
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