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

Kuck D, Bäther W (1986)
Organic Mass Spectrometry 21(8): 451-457.

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Abstract / Bemerkung
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 proton transfer in benzylbenzenium ions and contrasted to the fast interannular proton exchange in the higher homologues.
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Zeitschriftentitel
Organic Mass Spectrometry
Band
21
Zeitschriftennummer
8
Seite
451-457
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Kuck D, Bäther W. Inter- and intra-annular proton exchange in gaseous benzylbenzenium ions (protonated diphenylmethane). Organic Mass Spectrometry. 1986;21(8):451-457.
Kuck, D., & Bäther, W. (1986). Inter- and intra-annular proton exchange in gaseous benzylbenzenium ions (protonated diphenylmethane). Organic Mass Spectrometry, 21(8), 451-457. doi:10.1002/oms.1210210802
Kuck, D., and Bäther, W. (1986). Inter- and intra-annular proton exchange in gaseous benzylbenzenium ions (protonated diphenylmethane). Organic Mass Spectrometry 21, 451-457.
Kuck, D., & Bäther, W., 1986. Inter- and intra-annular proton exchange in gaseous benzylbenzenium ions (protonated diphenylmethane). Organic Mass Spectrometry, 21(8), p 451-457.
D. Kuck and W. Bäther, “Inter- and intra-annular proton exchange in gaseous benzylbenzenium ions (protonated diphenylmethane)”, Organic Mass Spectrometry, vol. 21, 1986, pp. 451-457.
Kuck, D., Bäther, W.: Inter- and intra-annular proton exchange in gaseous benzylbenzenium ions (protonated diphenylmethane). Organic Mass Spectrometry. 21, 451-457 (1986).
Kuck, Dietmar, and Bäther, Wolfgang. “Inter- and intra-annular proton exchange in gaseous benzylbenzenium ions (protonated diphenylmethane)”. Organic Mass Spectrometry 21.8 (1986): 451-457.
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