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Combining the Advantages of Tetrazoles and 1,2,3‐Triazoles: 4,5‐Bis(tetrazol‐5‐yl)‐1,2,3‐triazole, 4,5‐Bis(1‐hydroxytetrazol‐5‐yl)‐1,2,3‐triazole, and their Energetic Derivatives
Author(s) -
Dippold Alexander A.,
Izsák Dániel,
Klapötke Thomas M.,
Pflüger Carolin
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504624
Subject(s) - triazole , 1,2,4 triazole , tetrazole , combinatorial chemistry , chemistry , computer science , medicinal chemistry , organic chemistry
In the development of new energetic materials, the main challenge is the combination of high energy content with chemical and mechanical stability, two properties that are often contradictory. In this study, the syntheses and comprehensive characterizations of 4,5‐bis(tetrazole‐5‐yl)‐1,2,3‐triazole and the novel 4,5‐bis(1‐hydroxytetrazole‐5‐yl)‐1,2,3‐triazole, as well as their energetic properties, are presented, combining the advantages of the more energetic tetrazole and the more stable 1,2,3‐triazole rings. Nitrogen‐rich salts of both compounds were synthesized to investigate their detonation performances and combustion behavior calculated by computer codes for potential application in erosion‐reduced gun propellant mixtures due to their high nitrogen content. The structures of several of the compounds were studied by single‐crystal X‐ray diffraction and, especially in the case of 4,5‐bis(tetrazol‐5‐yl)‐1,2,3‐triazole, revealed the site of deprotonation.