Nitromethane Bridged Bis(1,3,4‐oxadiazoles): Trianionic Energetic Salts with Low Sensitivities
Abstract
Trianionic energetic salts based on one nitromethylene and two dinitromethyl anions were designed and synthesized. Interestingly, the unstable dinitromethylene group of diethyl 2,2′‐((dinitromethylene)bis(1,3,4‐oxadiazole‐5,2‐diyl))bis(2,2‐dinitroacetate) (2) was changed to a mononitromethylene group by an aminolysis reaction to form triammonium ((nitromethanidylene)bis(1,3,4‐oxadiazole‐5,2‐diyl))bis(dinitromethanide) (3), whereas in (dinitrobis(5‐(trinitromethyl)‐1,3,4‐oxadiazol‐2‐yl)methan) 8 it was hydrolyzed to a carbonyl group resulting in (bis(5‐(trinitromethyl)‐1,3,4‐oxadiazol‐2‐yl)methanone) 9. All the new compounds were fully characterized by infrared, multinuclear NMR spectra, and elemental analysis. The structures of triammonium ((nitromethanidylene)bis(1,3,4‐oxadiazole‐5,2‐diyl))bis(dinitromethanide) dihydrate (3⋅2 H2O) and bis(2‐dinitromethyl‐1,3,4‐oxadiazole‐5‐yl)methanone (9) were further confirmed by single‐crystal X‐ray diffraction analysis. Based on their different physical and detonation properties, some of the energetic salts were found to exhibit good energetic performance and low sensitivity.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Nov 28, 2017
- Source ID
- 10.1002/chem.201704939
Entities
People
- Damon A. Parrish
- Gregory H Imler
- Jean'ne Shreeve
- Qiong Yu
Organizations
- Defense Threat Reduction Agency
- M J Murdock Charitable Trust
- Office of Naval Research
- United States Naval Research Laboratory
- University of Idaho