Abstract
Abstract Kinetic deuterium isotope effects on the redox decomposition of hydroxymercurated propene, cis-, and trans-2-butenes in an aqueous solution (CH3CH(OH)CHRHg+→CH3COCH2R+Hg(0)+H+; R=H, CH3) were determined by following the reaction in situ by means of PMR spectroscopy. Taking advantage of the PMR characteristics, the identity of the reaction conditions was confirmed by comparing the rates for the reactant mixtures (e.g., CH3CH(OH)CH2Hg++CH3CD(OH)CH2Hg+). The mercurials, deuterated on either β-carbon (CH3CD(OH)CH2Hg+, CH3CD(OH)CHCH3Hg+) or α-carbon (CH3CH(OH)CDHHg+, CH3CH(OH)CDCH3Hg+), gave primary and secondary deuterium isotope effects of 1.35–1.40 and 1.17–1.19 respectively. A possible structure of the activated complex was proposed in accord with the observed nature of the intramolecular hydrogen shift.
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