Proton-catalyzed hydride transfer from alkanes to methylated benzyl cations : II. spectroscopy and kinetics. Isotope effects for proton exchange and hydride transfer

P. Pelt, van, H.M. Buck

Research output: Contribution to journalArticleAcademicpeer-review

2 Citations (Scopus)

Abstract

The PMR and UV spectra of para-X substituted 2,3,5,6-tetramethylbenzyl cations II (a-f) (X = OCH3, CH3, F, Br, H, NO2) are discussed and from the solvolytic behaviour of the parent benzyl chlorides the stability of these ions is found to be IIa > IIb > IIc > IId ~ IIe > IIf. Proton exchange between [2-3H]isobutane and HSO3F is found to have a small isotope effect of 6.5 at - 74°. The hydride-transfer reaction between labelled isobutane and ions IIb has a larger isotope-effect, estimated to be about 20. A termolecular transition state where transferred hydrogen is symmetrically bonded is proposed for the hydride-transfer reaction.
Original languageEnglish
Pages (from-to)206-209
JournalRecueil des Travaux Chimiques des Pays-Bas
Volume93
Issue number7
DOIs
Publication statusPublished - 1974

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