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

Study of selected benzyl azides by UV photoelectron spectroscopy and mass spectrometry
Study of selected benzyl azides by UV photoelectron spectroscopy and mass spectrometry
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
0022-2860
163-171
Pinto, R.M.
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Olariu, R.I.
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Lameiras, J.
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Martins, F.T.
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Dias, A.A.
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Langley, G.J.
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Rodrigues, P.
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Maycock, C.D.
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Santos, J.P.
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Duarte, M.F.
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Fernandez, M.T.
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Costa, M.L.
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Pinto, R.M.
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Olariu, R.I.
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Lameiras, J.
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Martins, F.T.
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Dias, A.A.
221a2ab3-3cc5-4635-b9df-bfce6f767364
Langley, G.J.
7ac80d61-b91d-4261-ad17-255f94ea21ea
Rodrigues, P.
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Maycock, C.D.
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Santos, J.P.
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Duarte, M.F.
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Fernandez, M.T.
a3fa520c-ba23-4259-95a4-02e1e0cc8aa1
Costa, M.L.
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Pinto, R.M., Olariu, R.I., Lameiras, J., Martins, F.T., Dias, A.A., Langley, G.J., Rodrigues, P., Maycock, C.D., Santos, J.P., Duarte, M.F., Fernandez, M.T. and Costa, M.L. (2010) Study of selected benzyl azides by UV photoelectron spectroscopy and mass spectrometry. Journal of Molecular Structure, 980 (1-3), 163-171. (doi:10.1016/j.molstruc.2010.07.009).

Record type: Article

Abstract

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

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Published date: September 2010
Organisations: Chemistry

Identifiers

Local EPrints ID: 346572
URI: http://eprints.soton.ac.uk/id/eprint/346572
ISSN: 0022-2860
PURE UUID: 9522e39c-cc67-4641-a7d0-e32fa4fafbb9
ORCID for G.J. Langley: ORCID iD orcid.org/0000-0002-8323-7235

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Date deposited: 03 Jan 2013 08:37
Last modified: 26 Nov 2019 02:04

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Contributors

Author: R.M. Pinto
Author: R.I. Olariu
Author: J. Lameiras
Author: F.T. Martins
Author: A.A. Dias
Author: G.J. Langley ORCID iD
Author: P. Rodrigues
Author: C.D. Maycock
Author: J.P. Santos
Author: M.F. Duarte
Author: M.T. Fernandez
Author: M.L. Costa

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