Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 25, Pages 8619-8626Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600769
Keywords
energetic materials; pyridine; salts; structure elucidation; thermally stable explosive
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Funding
- Ludwig-Maximilian University of Munich (LMU)
- Office of Naval Research (ONR) [ONR.N00014-16-1-2062]
- Bundeswehr - Wehrtechnische Dienststelle fur Waffen und Munition (WTD 91) [E/E91S/FC015/CF049]
- DAAD
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2,6-Bis(picrylamino) pyridine (1; pre-PYX) and 2,6bis-(picrylamino)-3,5-dinitropyridine (2; PYX) were synthesized using an improved literature method. Compounds 1 and 2 were reinvestigated in detail and the X-ray structures (1: rho = 1.698 g cm(-3) at 173 K; 2: rho = 1.757 g cm(-3) at 298 K) are given. The reactions of 2 with different bases, such as alkali metal hydroxides (sodium, potassium, rubidium, cesium), and N-bases (ammonia, hydrazine, hydroxylamine, guanidinium carbonate, aminoguanidine bicarbonate) are reported, as well as metathesis reactions producing energetic salts. Several energetic compounds were synthesized and characterized for the first time using vibrational (IR, Raman) and multinuclear NMR spectroscopy, mass spectrometry, elemental analysis, and DSC. The crystal structures of four energetic salts were determined using low temperature single-crystal X-ray diffraction. Heats of formation for the metal-free species were calculated using the Gaussian 09 software. Detonation parameters were estimated using the EXPLO5 program. The sensitivities towards impact, friction, and electrostatic discharge were also determined.
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