Synthesis and Characterization of the New Heterocycle 5-(4-Amino-1,2,4-triazol-3-on-5′-yl)-1H-tetrazole and Some Ionic Nitrogen-Rich Derivatives

A new heterocycle consisting of a tetrazole ring attached to an amino‐triazolone ring, namely 5‐(4‐amino‐1,2,4‐triazol‐3‐on‐5′‐yl)‐1H‐tetrazole (3) as well as its ammonium (2), hydroxylammonium (3), and sodium salt (4), is introduced. Its ammonium salt (2) is formed starting from tetrazole‐5‐carboxa...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2014-01, Vol.51 (1), p.85-95
Main Authors: Fischer, Niko, Hüll, Katharina, Klapötke, Thomas M., Stierstorfer, Jörg
Format: Article
Language:English
Subjects:
Diffraction
Electrostatic discharges
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Summary:A new heterocycle consisting of a tetrazole ring attached to an amino‐triazolone ring, namely 5‐(4‐amino‐1,2,4‐triazol‐3‐on‐5′‐yl)‐1H‐tetrazole (3) as well as its ammonium (2), hydroxylammonium (3), and sodium salt (4), is introduced. Its ammonium salt (2) is formed starting from tetrazole‐5‐carboxamide oxime (1), which is reacted with diaminourea (carbonyldihydrazide) in aqueous media. All compounds 2, 3, 4, 5 were structurally characterized by single crystal X‐ray diffraction. The thermal behavior was investigated using differential scanning calorimetry, and the sensitivities towards impact, friction, and electrostatic discharge were determined. Furthermore, several detonation parameters were calculated with the program EXPLO5 to determine the potential use of these compounds as highly energetic materials.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.1877