Study of selected benzyl azides by UV photoelectron spectroscopy and mass spectrometry

Rui Montenegro Pinto, Romeo Iulian Olariu, J. Lameiras, Filipa T. Martins, António Alberto Dias, G. John Langley, Paula R. S. Rodrigues, Christopher D. Maycock, José Paulo Santos, M. Filomena Duarte, M. Tereza Fernandez, Maria de Lourdes Costa

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10 Citations (Scopus)


Benzyl azide and the three methylbenzyl azides were synthesized and characterized by mass spectrometry (MS) and ultraviolet photoelectron spectroscopy (UVPES). The electron ionization fragmentation mechanisms for benzyl azide and their methyl derivatives were studied by accurate mass measurements and linked scans at constant B/E. For benzyl azide, in order to clarify the fragmentation mechanism, labelling experiments were performed. From the mass analysis of methylbenzyl azides isomers it was possible to differentiate the isomers ortho, meta and para. The abundance and nature of the ions resulting from the molecular ion fragmentation, for the three distinct isomers of substituted benzyl azides, were rationalized in terms of the electronic properties of the substituent. Concerning the para-isomer, IRC calculations were performed at UHF/6-31G(d) level. The photoionization study of benzyl azide, with He(I) radiation, revealed five bands in the 8-21 eV ionization energies region. From every photoelectron spectrum of methylbenzyl azides isomers it has been identified seven bands, on the same range as the benzyl azide. Interpretation of the photoelectron spectra was accomplished applying Koopmans' theorem to the SCF orbital energies obtained at HF/6-311++G(d, p) level.

Original languageEnglish
Pages (from-to)163-171
Number of pages9
JournalJournal Of Molecular Structure
Issue number1-3
Publication statusPublished - 10 Sep 2010


  • Benzyl azides
  • EIMS
  • IRC calculations


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