Nitratoethyl-5 H -tetrazoles: improving the oxygen balance through application of organic nitrates in energetic coordination compounds

• Published in: Dalton transactions : an international journal of inorganic chemistry 2021-08, Vol.50 (31), p.10811-10825
• Main Authors: Gruhne, Michael S., Lenz, Tobias, Rösch, Markus, Lommel, Marcus, Wurzenberger, Maximilian H. H., Klapötke, Thomas M., Stierstorfer, Jörg
• Format: Article
• Language: English
• ISSN: 1477-9226; 1477-9234
• DOI: 10.1039/D1DT01898A

1- and 2-Nitratoethyl-5 H -tetrazole (1-NET and 2-NET) were prepared through nitration of the respective alkyl alcohol using 100% nitric acid. A mixture of 1- and 2-hydroxyethyl-5 H -tetrazole was obtained after alkylation of 1,5 H -tetrazole. Also, a one-pot synthesis of 1-hydroxyethyl-5 H -tetrazole was developed enabling the selective preparation of 1-NET. Both organic nitrates were characterized by 1 H, 13 C, and 1 H– 15 N HMBC NMR spectroscopy. In addition, calculations using the Hirshfeld method and the EXPLO5 code were performed. Principally, 20 energetic coordination compounds involving the d-metals Mn, Cu, Zn, and Ag, each structurally characterized by low temperature single crystal X-ray diffraction, were prepared based on 1-NET and 2-NET. Of these complexes, 18 were obtained as pure bulk materials, and therefore, characterized for impact, friction, and ball drop impact sensitivity, as well as electrostatic discharge and thermal stability using differential thermal analysis. Hot plate and hot needle tests were performed mostly showing strong deflagrations making the complexes candidates for green combustion catalysts. Furthermore, successful PETN initiation experiments were carried out for several complexes and all ECCs were investigated by laser ignition experiments.