Volume 145, 2010
From the journal:

Faraday Discussions

Methylene-transfer reactions of benzylium/tropylium ions with neutral toluene studied by means of ion-trap mass spectrometry

Emilie-Laure Zins,a   Claude Pepea  and  Detlef Schröder*b  

* Corresponding authors

a Laboratoire de Dynamique, Interactions et Réactivité, UMR 7075 CNRS/UPMC, Université Pierre et Marie Curie, 4 Place Jussieu, Paris Cedex 05, France

b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo námesti 2, Prague 6, Czech Republic

Abstract

The ion–molecule reactions of C7H7+ ions with neutral toluene are investigated in an ion-trap mass spectrometer, which is shown to be suitable instrumentation for kinetic studies, although the absolute rate constant can only be derived with difficulties. The benzylium ions C6H5CH2+ undergo a formal CH2+ transfer with toluene to afford the corresponding xylenium ions, CH3–C6H4–CH2+, whereas the tropylium ions c-C7H7+ do not react. The results for the parent compound C7H7+ are complemented with data for the tert-butyl derivative generated by collision-induced dissociation of the corresponding p-(tert-butyl)benzyl pyridinium ion. For the tert-butyl substituted ion, the benzylium/tropylium dichotomy exists in a similar manner in that reactive and non-reactive fractions are observed, of which the former is assigned to the benzylium structure on the basis of infrared-multiphoton dissociation spectra.

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Article information

DOI
https://doi.org/10.1039/B907236E
Article type
Paper
Submitted
08 Apr 2009
Accepted
26 May 2009
First published
21 Sep 2009

Faraday Discuss., 2010,145, 157-169

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Methylene-transfer reactions of benzylium/tropylium ions with neutral toluene studied by means of ion-trap mass spectrometry

E. Zins, C. Pepe and D. Schröder, Faraday Discuss., 2010, 145, 157 DOI: 10.1039/B907236E

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