publication . Article . 1986

Inter- and intra-annular proton exchange in gaseous benzylbenzenium ions (protonated diphenylmethane)

Dietmar Kuck; Wolfgang Bäther;
Open Access
  • Published: 01 Jan 1986 Journal: Organic Mass Spectrometry, volume 21, pages 451-457 (issn: 0030-493X, eissn: 1096-9888, Copyright policy)
  • Publisher: Wiley
  • Country: Germany
Abstract
Two distinct proton exchange reactions occur in metastable gaseous benzylbenzenium ions, generated by isobutane chemical ionization of diphenylmethane and four deuterium-labelled analogues. Whereas the proton ring-walk at the benzenium moiety is fast giving rise to a completely random intraannular proton exchange, the interannular proton exchange is surprisingly slow and competes with the elimination of benzene. A kinetic isotope effect of kH/kD= 5 has been determined for the interannular proton transfer, and a particularly high energy barrier of 50-75 kJ mol-1 has been estimated. These observations are attributed to steric restrictions of the ring-to-ring proto...
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Subjects
arXiv: Nuclear ExperimentNuclear Theory
free text keywords: Instrumentation, Molecular Medicine, Biochemistry, 540, Nuclear chemistry, Diphenylmethane, chemistry.chemical_compound, chemistry, Protonation, Proton, Kinetic isotope effect, Chemical ionization, Steric effects, Ion, Photochemistry, Deuterium
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