Electron-ionization-Induced fragmentation of N-monosubstituted 2-phenylacetamides

Authors

  • Ljiljana A. Jeremić,

    1. Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, PO Box 494, YU-11001, Belgrade, Yugoslavia
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  • Nestor L. Kobilarov,

    1. Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, PO Box 494, YU-11001, Belgrade, Yugoslavia
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  • Slobodan D. Petrović

    Corresponding author
    1. Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, PO Box 494, YU-11001, Belgrade, Yugoslavia
    • Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, PO Box 494, YU-11001, Belgrade, Yugoslavia
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Abstract

Electron-ionization-induced mass spectra of N-monosubstituted 2-phenylacetamides were recorded and their fragmentation patterns were studied by metastable-ion analyses. Representative deuterated analogues of these compounds have also been synthesized and their mass spectra compared with those of the unlabelled parent compounds. The most typical fragmentation for N-alkyl-, N-isoalkyl- and N-cycloalkyl-2-phenylacetamides is cleavage of the bond β to the carbonyl function, resulting in an ion fragment of m/z 92, following the transfer of hydrogen and elimination of a corresponding ketene. The primary fragmentation process for N-aryl substituted 2-phenylacetamides is the loss of an aromatic hydrogen atom from the molecular ion. The other principal fragmentation processes observed with these compounds are discussed.

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