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Article << Previous     |     Next >>   Contents Vol 65(12)

Mass Spectrometry of Cyclopentadienylideneketene: Differentiation of Isomeric Ion Structures by Means of Ion/Molecule Reactions

Pascal Gerbaux A C and Curt Wentrup B C

A Mass Spectrometry Research Group, Interdisciplinary Center for Mass Spectrometry, University of Mons, UMONS, 23 Place du Parc, B-7000 Mons, Belgium.
B School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.
C Corresponding authors. Email: wentrup@uq.edu.au; Pascal.Gerbaux@umons.ac.be

Australian Journal of Chemistry 65(12) 1655-1661 http://dx.doi.org/10.1071/CH12327
Submitted: 11 July 2012  Accepted: 16 August 2012   Published: 13 September 2012

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The nature of the m/z 104 ions formed by loss of CO2 or Ph-O-NCO from the molecular ions of phthalic anhydride, N-phenoxyphthalimide, and N-phenoxyisophthalimide was investigated by means of ion/molecule reactions with acetone. This allows a clear-cut differentiation of the so-obtained ions from the isomeric molecular ions of cyclopentadienylideneketene. The different intrinsic chemical reactivities of ionized cyclopentadienylideneketene and its distonoid isomer towards neutral acetone were investigated on a large-scale hybrid mass spectrometer and confirmed by density functional theory calculations.


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