Increasing the limits of energy and safety in tetrazoles: dioximes as unusual precursors to very thermostable and insensitive energetic materials

Abstract

Donor-acceptor hydrogen (H)-bonding contributes to good temperature resistance for energetic compounds. Now we report a strategy which maximizes donor-acceptor H-bonding sites in the construction of new energetic compounds. The straightforward...

Increasing the Energy Limit of Single Triazole–Tetrazole: HNANTT Modified with Its Energetic Coordination Polymers, Co-Crystals, and Energetic Salts

“…Noncovalent interactions, including hydrogen bonds and π–π interactions, are commonly combined with decomposition temperatures ( T d ) to explain the thermal stability of energetic materials. − All materials in this study were dried before analysis to avoid the effects of crystal water (Figure ). The thermal stabilities of HNANTT, NANTT-ECPs, NANTT energetic salts, and NANTT co-crystal were measured by differential scanning calorimetry (DSC) with a heating rate of 5 K min –1 under a nitrogen atmosphere from 50 to 400 °C.…”

Polynitro-functionalized 4-phenyl-1H-pyrazoles as heat-resistant explosives

“…All the compounds prepared in this study were thoroughly characterized by NMR [ 1 H, 13 C{ 1 H}, and, in a few cases, 15 N NMR] spectra, IR, HRMS and elemental analysis studies. Signals corresponding to the methyl group in 3-14 were observed in the range of 4.28-4.38 ppm in the 1 H NMR spectra, and 41.19-43.71 ppm in the 13 C{ 1 H} NMR spectra.…”

“…11,12 Recently, there has been a surge in the number of new energetic compounds based on nitrogen and oxygen-rich heterocyclic ring systems like azoles, oxadiazoles, pyrazine, tetrazene, etc. [13][14][15][16][17][18][19][20][21][22] Energetic materials with such nitrogen-based heterocyclic rings as their backbone are highly endothermic and considered environmentally friendly as they release non-toxic dinitrogen (N 2 ) gas after their decomposition. Therefore, recently, several heat-resistant explosives based on polynitrobenzene moieties connected to nitrogen-rich heterocyclic rings have been reported.…”

A Dihydrazone as a Remarkably Nitrogen-Rich Thermostable and Insensitive Energetic Material

“…However, energetic materials (EMs) with oxime or hydrazone groups have not been thoroughly studied . We demonstrated recently that dioximes have good potential to be used as EMs, owing to their acceptable densities, molecular stability, and insensitivity . Now we demonstrate that intra- and intermolecular interactions arising from the presence of two hydrazone functionalities support low solubility in water and reduced acidity, properties that are desirable for practical applications.…”

“…30 We demonstrated recently dioximes have good potential to be used as EMs, owing to their acceptable densities, molecular stability, and insensitivity. 31 Now we demonstrate that intra-and intermolecular interactions arising from the presence of two hydrazone functionalities support low solubility in water and reduced acidity, properties that are desirable for practical applications. The high-energy-density compound of insensitive nature, 1,2-dihydrazono-1,2-di(1Htetrazol-5-yl)ethane (4), with high nitrogen content was synthesized from the dioxime derivative (2).…”