A study of gaseous benzenium and toluenium ions generated from 1,4- dihydro- and 1-methyl-1,4-dihydro-benzoic acids

Kuck D, Schneider J, Grützmacher H-F (1985)
Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry 1985(5): 689-696.

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Journal Article | Published | English
Abstract
Gaseous benzenium C6H7+(1) and toluenium C7H9+(2) ions have been generated by mass spectrometric loss of CO2H from the corresponding 1,4-dihydrobenzoic acids (3) and (4), and their fragmentations after ca. 10 µs have been investigated by means of mass-analysed ion kinetic energy (MIKE) spectrometry of some 2H and 13C labelled analogues. Metastable C6H7+ ions eliminate H2 after proton randomization, whereas metastable C7H9+ ions expel both H2 and CH4 after incomplete proton equilibration. In particular, 40% of C7H9+ ions randomize all their carbon and hydrogen atoms prior to loss of CH4, and 60% of C7H9+ ions lose the original methyl group along with a hydrogen atom from the (proton-equilibrated) benzenium ring, accompanied by a slow and incomplete exchange between the hydrogen atoms of the ring and the methyl group. It is suggested that loss of both CH4 and H2 occur via the (ipso-)toluenium ion (2). The role of a non-classical C7H9+ isomer, phenylmethonium ion (6), is discussed since striking similarities are found compared with [C6H6·CH3+]* adducts from ion–molecule reactions described in the literature.
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Kuck D, Schneider J, Grützmacher H-F. A study of gaseous benzenium and toluenium ions generated from 1,4- dihydro- and 1-methyl-1,4-dihydro-benzoic acids. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry. 1985;1985(5):689-696.
Kuck, D., Schneider, J., & Grützmacher, H. - F. (1985). A study of gaseous benzenium and toluenium ions generated from 1,4- dihydro- and 1-methyl-1,4-dihydro-benzoic acids. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry, 1985(5), 689-696.
Kuck, D., Schneider, J., and Grützmacher, H. - F. (1985). A study of gaseous benzenium and toluenium ions generated from 1,4- dihydro- and 1-methyl-1,4-dihydro-benzoic acids. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry 1985, 689-696.
Kuck, D., Schneider, J., & Grützmacher, H.-F., 1985. A study of gaseous benzenium and toluenium ions generated from 1,4- dihydro- and 1-methyl-1,4-dihydro-benzoic acids. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry, 1985(5), p 689-696.
D. Kuck, J. Schneider, and H.-F. Grützmacher, “A study of gaseous benzenium and toluenium ions generated from 1,4- dihydro- and 1-methyl-1,4-dihydro-benzoic acids”, Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry, vol. 1985, 1985, pp. 689-696.
Kuck, D., Schneider, J., Grützmacher, H.-F.: A study of gaseous benzenium and toluenium ions generated from 1,4- dihydro- and 1-methyl-1,4-dihydro-benzoic acids. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry. 1985, 689-696 (1985).
Kuck, Dietmar, Schneider, Jens, and Grützmacher, Hans-Friedrich. “A study of gaseous benzenium and toluenium ions generated from 1,4- dihydro- and 1-methyl-1,4-dihydro-benzoic acids”. Journal of the Chemical Society, Perkin Transactions 2, Physical Organic Chemistry 1985.5 (1985): 689-696.
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