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Synthesis and Investigation of 2,6‐Bis(picrylamino)‐3,5‐dinitro‐pyridine (PYX) and Its Salts
Author(s) -
Klapötke Thomas M.,
Stierstorfer Jörg,
Weyrauther Michael,
Witkowski Tomasz G.
Publication year - 2016
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.201600769
Subject(s) - chemistry , salt metathesis reaction , alkali metal , pyridine , raman spectroscopy , inorganic chemistry , metathesis , infrared spectroscopy , potassium , rubidium , medicinal chemistry , organic chemistry , polymerization , physics , optics , polymer
2,6‐Bis(picrylamino)pyridine ( 1 ; pre‐PYX) and 2,6‐bis(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 : ρ =1.698 g cm −3 at 173 K; 2 : ρ =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.