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Nitromethane Bridged Bis(1,3,4‐oxadiazoles): Trianionic Energetic Salts with Low Sensitivities
Author(s) -
Yu Qiong,
Imler Gregory H.,
Parrish Damon A.,
Shreeve Jean'ne M.
Publication year - 2017
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.201704939
Subject(s) - nitromethane , aminolysis , chemistry , oxadiazole , single crystal , hydrolysis , crystal structure , medicinal chemistry , crystallography , polymer chemistry , organic chemistry , catalysis
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 H 2 O) 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.