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The Contribution of Quantum Mechanical Tunneling To the 1,2-Hydrogen Rearrangement of Methylbromocarbene

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The rate constants for the 1,2-hydrogen rearrangement of methyl- and methyl-d3-bromocarbene have been determined as a function of temperature. The Arrhenius plots are curved, and the intermolecular isotope effect is small and may increase with increasing temperature. We believe that although the rearrangement proceeds classically at high temperatures, as suggested by theory, quantum mechanical tunneling contributes significantly to the reaction at low temperatures. Alternative explanations are presented and discussed.

Affiliations: 1: Department of Chemistry, University of Rochester, Rochester, NY 14627, U.S.A.


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