Nitrogen-Rich Salts of 1-Methyl-5-nitriminotetrazolate: An Auspicious Class of Thermally Stable Energetic Materials

Abstract

was formed by nitration of 1-methyl-5-aminotetrazole, which was obtained by methylation of sodium 5-aminotetrazolate. 1 was deprotonated using potassium hydroxide forming the corresponding potassium salt (2), which was transformed into silver 1-methyl-5-nitriminotetrazolate (3) by the reaction with silver nitrate. Guanidinium (4), 1-aminoguanidinium (5), 1,3-diaminoguanidinium ( 6), 1,3,5-triaminoguanidinium (7), and azidoformamidinium (8) 1-methyl-5nitriminotetrazolate were prepared by metathesis reactions either using 2 and guanidinium perchlorates or 3 and guanidinium chlorides under the precipitation of KClO 4 or AgCl, respectively. All compounds were fully characterized by single crystal X-ray diffraction, vibrational spectroscopy, multinuclear NMR spectroscopy, elemental analysis, differential scanning calorimetry (DSC) as well as bomb calorimetry. Since the packing of molecules in the solid state influences the properties of materials significantly, a detailed description of the crystal structures of 3, 4, 6, 7, and 8 is given. Using the heats of combustion the heats of formations were calculated to be strongly endothermic. Several detonation parameters like the detonation pressure and detonation velocity were calculated using the EXPLO5 software. In addition the sensitivities were tested using the BAM drop hammer and friction tester. With respect to developing new high explosives triaminoguanidinium 1-methyl-5-nitriminotetrazolate shows the most promising values and was therefore successfully tested in a Koenen Test (critical diameter e 10 mm).

Computational studies on tetrazole derivatives as potential high energy materials

“…Different tetrazole derivatives such as salts of 5,5 0 -azotetrazole [12], bistetrazoles [13], the perchlorate and nitrate of 1,5-diaminotetrazole [14], salts of 1-methyl-5-nitriminotetrazolate [15], alkali metal 5,5 0 -hydrazinebistetrazolate salts [16], 5-nitroaminotetrazole salts [17], and organic salts of nitrotetrazole [18] have been tested as potential materials for modifying the combustion rates of rocket propellants, as gas generators and explosive materials.…”

Computational Study of Coordinated Ni(II) Complex with High Nitrogen Content Ligands

“…A variety of derivatives-involve tetrazole have recently been synthesized in experiment [18, 19] and verified a good selectivity for coordination with Ni(II). Consequently tetrazole with four potential coordinated nitrogen atoms which are ready to bridge transition metals of our required binuclear transition metal complexes, become the candidate group.…”

Backbone NxH compounds at high pressures

“…There are numerous reports on synthesis of complex energetic materials containing chains of nitrogen atoms: N5, N8, and even N10 [6][7][8] and complex "salts" such as TAG-MNT [9], but these materials require other elements for stabilization and their synthesis remains quite challenging. Rich in nitrogen N-H systems appear to be the most attractive as they would be the most energy-density efficient and because hydrogen tends to stabilize low bond order nitrogen compounds (e.g., hydrazine).…”