Synthesis and Characterization of Binary, Highly Endothermic, and Extremely Sensitive 2,2 '-Azobis(5-azidotetrazole)

Benz, Maximilian; Klapoetke, Thomas M.; Stierstorfer, Joerg and Voggenreiter, Michael (2022): Synthesis and Characterization of Binary, Highly Endothermic, and Extremely Sensitive 2,2 '-Azobis(5-azidotetrazole). In: Journal of the American Chemical Society, Vol. 144, No. 14: pp. 6143-6147

Abstract

2,2 '-Azobis(5-azidotetrazole) (C2N16,3), a highly energetic nitrogen-rich binary CN compound was obtained in athree-step synthesis through the formation of 5-azidotetrazole (1), subsequent amination usingO-tosylhydroxylamine to give 2-amino-5-azidotetrazole (2), and oxidative azo coupling of2usingtBuOCl as an oxidant in MeCN. A nitrogen:carbon ratio of 8:1,eight nitrogen atoms in a row, and a nitrogen content of over 90% was unknown for a binary heterocyclic compound until now. Thesuccessful isolation was confirmed through X-ray diffraction as well as by vibrational and13C NMR spectroscopy. C2N16can explodeinstantly and shows mechanical sensitivities far higher than quantitatively measurable. Nevertheless, it features interesting energeticperformances, which were calculated using different quantum-chemical methods.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0002-7863
• Language: English