Experimental Detection of the Pentazole Anion, N5(-)

The pentazole anion has been generated from para-hydroxyphenylpentazole and identified by electrospray ionization mass spectrometry. Whereas at low collision voltages the para-phenoxypentazole anion undergoes stepwise N2 elimination generating the corresponding azide and nitrene, at high collision v...

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Bibliographic Details
Main Authors: Vij, Ashwani, Pavlovich, James G, Wilson, William W, Christe, Karl O
Format: Report
Language:English
Subjects:
AQ-M03-02-0026
AZIDES
ELECRTOSPRAY IONIZATION MASS SPECTROMETRY
ELIMINATION REACTIONS
NITRENE
NITROGEN HETEROCYCLIC COMPOUNDS
Organic Chemistry
PARA-HYDROXYPHENYLPENTAZOLE
PARA-PHENYLPENTAZOLE ANION
PENTAZOLE ANION
PENTAZOLE/PARA-HYDROXYPHENYL
PHENYLPENTAZOLE
SYNTHESIS(CHEMISTRY)
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Summary:The pentazole anion has been generated from para-hydroxyphenylpentazole and identified by electrospray ionization mass spectrometry. Whereas at low collision voltages the para-phenoxypentazole anion undergoes stepwise N2 elimination generating the corresponding azide and nitrene, at high collision voltages the N5(-) anion is formed. Fragmentation of the pentazole anion produces the N3(-) anion as the principal negative ion. These experiments provide the first experimental proof for the existence of the pentazole anion. They also demonstrate that under suitable reaction conditions the C-N bond in a phenylpentazole can selectively be broken with conservation of the pentazole ring, thus providing a potential synthetic route to the pentazole anion. Performed in cooperation with Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, CA.