Canadian Journal of Chemistry

The kinetics of proton and deuteron transfer from 4-nitrophenylnitromethane and l-(4-nitrophenyl)-l-nitroethane to 2, 7-dimethoxy-l, 8-bis (dimethylamino) naphthalene …

KT Leffek, P Pruszynski

Index: Leffek, Kenneth T.; Pruszynski, Przemyslaw Canadian Journal of Chemistry, 1981 , vol. 59, p. 3034 - 3038

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Citation Number: 8

Abstract

4-Nitrophenylnitromethane reacts with 2, 7-dimethoxy-1, 8-bis (dimethylamino) naphthalene in acetonitrile in a bimolecular proton transfer, which shows a primary deuterium isotope effect, k H/k D= 12.2 at 25° C. The large isotope effect on the enthalpy of activation,(Δ HD≠- ΔH H≠)= 4.6±0.3 kcal mol-1 is consistent with a significant contribution of proton tunnelling to the reaction rate of the protium substrate. The analogous reaction of 1-(4-nitrophenyl)-1- ...