Gold(I) and silver(I) complexes of 1-methyl-5-thio-tetrazole (1) have been prepared and the coordination chemistry of this ligand toward metal-phosphine frameworks has been explored. As indicated by IR and Raman data, ligand 1 is deprotonated and the resulted anion acts as a bidentate (S,N)-tetrazole-5-thiolato unit in the new gold(I) complexes, [Au(SCN(4)Me)(PPh(3))] (2), [{Au(SCN(4)Me)}(2)(μ-dppm)] (3), and [{Au(SCN(4)Me)}(2)(μ-dppe)] (4), while it is coordinated only through the sulfur atom as its neutral tetrazole-5-thione form in the silver(I) derivative, [Ag(HSCN(4)Me)(PPh(3))](2)(OTf)(2) (5). Further characterization of the new compounds was performed using multinuclear ((1)H, (13)C, (31)P, (19)F) NMR spectroscopy, mass spectrometry, and DSC measurements. Single-crystal X-ray diffraction studies revealed basically linear P-M-S arrangements in complexes 3-5. The bidentate (S,N) coordination pattern results in a T-shaped (S,N)PAu core in 3 and 4, whereas, in 5, a similar coordination geometry is achieved in the dimer association based on S-bridging ligand 1. Herein, weak (C)H···Au and (C)H···Ag agostic interactions were observed. An intramolecular Au···Au contact occurs in 3, while in 4 intermolecular aurophilic bonds lead to formation of a chain polymer. An intermolecular Ag···Ag contact is also present in the dimer unit of 5. Low-temperature (31)P NMR data for 5 evidenced the presence of monomer and dimer units in solution. Theoretical calculations on model of the complexes 2 and 4 are consistent with the geometries found by X-ray diffraction studies.
The dilithium (1), disodium (2), dipotassium (3) and dicesium (4) salt as well as the calcium (5), strontium (6) and barium (7) salt of 5,5'-bis(1-hydroxytetrazole) were prepared and characterized including NMR-, IR-and Raman spectroscopy, mass spectrometry, elemental analysis and differential scanning calorimetry. The crystal structures of 1, 2 and 4-6 were additionally determined by single-crystal X-ray diffraction. The sensitivities of the salts towards impact, friction and electrostatic discharge were determined by means of BAM (Bundesanstalt für Materialforschung-und prüfung) methods. The potential use of 1, 6 and 7 as coloring agents in pyrotechnical mixtures as well as the utilization of 3 and 4 as additives in near infrared (NIR) emitting pyrotechnical formulations was examined.
International audienceDiaminouronium 5-nitriminotetrazolate (1) and diaminouronium 1-methyl-5-nitrimino-tetrazolate (2) were synthesized by the reaction of diaminourea with 5-nitriminotetrazole (3) and 1-methyl-5-nitriminotetrazole (4), respectively. The energetic compounds 1 and 2 were fully characterized by single crystal X-ray diffraction, NMR spectroscopy, IR- and Raman spectroscopy as well as DSC measurements. The sensitivities towards impact, friction and electrical discharge were determined. In addition, several detonation parameters (e.g. heat of explosion, detonation velocity) were computed by the EXPLO5 computer code based on calculated (CBS-4M) heat of formation and X-ray densities
Alkaline metal salts are widely used in pyrotechnic formulations. For NIR pyrotechnics, potassium, and cesium nitrate are mainly used as oxidizers and infrared emitters. Herein, new NIR illuminant formulations were tested using several potassium and cesium salts of high‐nitrogen compounds such as tetrazole and triazole derivatives. The research of new formulations comprises the evaluation of sensitivity data and radiometric measurements of new formulations. It was further investigated whether the IR emission can be improved using different nitrogen releasing agents like aminotetrazole or diethylene triamine trinitrate (DETT) as hexamethylenetetramine replacements.
The title compound, 1,3‐dinitramino‐2‐nitroxy‐propane (1) was prepared in high yield (85 %) and characterized by multinuclear NMR (1H, 13C, 14N) and vibrational (IR, Raman) spectroscopy. The molecular structure in the solid state was elucidated by single crystal X‐ray diffraction. 1 crystallizes in the orthorhombic space group Pnma with a crystal density of ρ = 1.798 g cm−3. Compound 1 melts at 166 °C and decomposes at 168 °C. The impact (7 J), friction (96 N) and electrostatic discharge sensitivities (0.6 J) were determined experimentally. The detonation parameters of 1 were calculated using a combined quantum chemical (CBS‐4M) calculation and a chemical equilibrium calculation based on the steady‐state model of detonation: Q = −5998 kJ kg−1, P = 339 kbar, D = 8895 m s−1. The experimentally determined detonation velocity (fiber optic method) agrees well with the calculated values. In comparison with picric acid (PA) and nitropenta (PETN), compound 1 shows superior detonation characteristics when detonated in a confined space.
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