Asymmetric: N, N ′-ethylene-bridged azole-based compounds: Two way control of the energetic properties of compounds

Dheeraj Kumar, Lauren A. Mitchell, Damon A. Parrish, Jean'Ne M. Shreeve

Research output: Contribution to journalArticlepeer-review

40 Scopus citations


Reactions of various energetic pyrazole, triazole and tetrazole salts with 1-(2-bromoethyl)-5-aminotetrazole, in the presence of a phase transfer catalyst, resulted in new asymmetric N,N′-ethylene-bridged azole-based energetic compounds having diversified functionalities and properties. The availability of the aminotetrazole moiety for conversion to nitroimino(tetrazole) provides a route for further modifying energetic properties. All the compounds were thoroughly characterized by IR, NMR [1H, 13C{1H}, 15N], elemental analyses, and differential scanning calorimetry (DSC). Some were also further characterized using single-crystal X-ray diffraction studies. Impact and friction sensitivities were measured and heats of formation and detonation performances were calculated. Results show that combination of different energetic heterocycles broadens options for the design of desirable energetic compounds.

Original languageEnglish (US)
Pages (from-to)9931-9940
Number of pages10
JournalJournal of Materials Chemistry A
Issue number25
StatePublished - 2016

Bibliographical note

Funding Information:
Financial support from the Office of Naval Research (N00014-16-1-2089), and the Defense Threat Reduction Agency (HDTRA 1-15-1-0028) are gratefully acknowledged

Publisher Copyright:
© 2016 The Royal Society of Chemistry.

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


Dive into the research topics of 'Asymmetric: N, N ′-ethylene-bridged azole-based compounds: Two way control of the energetic properties of compounds'. Together they form a unique fingerprint.

Cite this