Energetic Salts Based on 3,5-Bis(dinitromethyl)-1,2,4-triazole Monoanion and Dianion: Controllable Preparation, Characterization, and High Performance

Jiaheng Zhang, Srinivas Dharavath, Lauren A. Mitchell, Damon A. Parrish, Jean'Ne M. Shreeve

Research output: Contribution to journalArticlepeer-review

105 Scopus citations

Abstract

Molecular modification of known explosives is considered to be an efficient route to design new energetic materials. A new family of energetic salts based on the 3,5-bis(dinitromethyl)-1,2,4-triazole monoanion and dianion were controllably synthesized by using 1-diamino-2,2-dinitroethene as a precursor. X-ray structure determination of monohydrazinium 3,5-bis(dinitromethyl)-1,2,4-triazolate (5) and monoammonium (6) and diammonium 3,5-bis(dinitromethyl)-1,2,4-triazolate hydrate (8·H2O) further confirmed the structures of these anions. In addition, as supported by X-ray data, in the monoanion system, the roving proton on the ring nitrogen rather than on the gem-dinitro carbon results in extensive hydrogen-bonding interactions and higher packing coefficients. Interestingly, 5 and 6 possess the highest calculated crystal densities, 1.965 and 1.957 g cm-3 at 150 K, for hydrazinium and ammonium energetic salts, respectively. Energetic evaluation indicates that 5 (detonation velocity vD = 9086 m s-1 detonation pressure P = 38.7 GPa) and 6 (vD, 9271 m s-1 P = 41.0 GPa) exhibit great detonation properties, superior to those of current highly explosive benchmarks, such as 1,3,5-trinitroperhydro-1,3,5-triazine (RDX) and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX).

Original languageEnglish (US)
Pages (from-to)7500-7503
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number24
DOIs
StatePublished - Jun 22 2016

Bibliographical note

Funding Information:
Financial support of the Office of Naval Research (NOOO14-16-1-2089), the Defense Threat Reduction Agency (HDTRA 1-15-1-0028), and CFD Research Corporation are gratefully acknowledged.

Publisher Copyright:
© 2016 American Chemical Society.

Copyright:
Copyright 2016 Elsevier B.V., All rights reserved.

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