122299-64-3Relevant academic research and scientific papers
CH ACIDITY OF SUBSTITUTED CYCLOALKANES. V. THE KINETIC ISOTOPE EFFECT OF HYDROGEN EXCHANGE IN PHENYLCYCLOALKANES
Zharova, N. G.,Shapiro, O. I.
, p. 602 - 609 (2007/10/02)
The kD/kT value for the isotope exchange of hydrogen in phenylcycloalkanes with cyclohexylamine (catalyzed by lithium cyclohexylamide) and with dimethyl sulfoxide decreases from 2.0 - 2.5 (for phenylcyclopentane and phenylcyclooctane) to 1.3 - 1.4 (for phenylcyclopropane).It was concluded that the reaction rate in the listed catalytic systems is controlled by the ionization of the CH acid.The relationships governing the variation of the kD/kT values in the ionization of phenylcycloalkanes are explained by the effect of structural rearrangement in the anionic fragments of the hydrocarbons on the mechanism of the elementary proton transfer event.
