Synthesis and promising properties of a new family of high-density energetic salts of 5-nitro-3-trinitromethyl-1H-1,2,4-triazole and 5,5'-bis(trinitromethyl)-3,3'-azo-1H-1,2,4-triazole

Salts of trinitromethyl-substituted triazoles, 5-nitro-3-trinitromethyl-1H-1,2,4-triazole and 5,5'-bis(trinitromethyl)-3,3'-azo-1H-1,2,4-triazole (5), form a new class of highly dense energetic materials. Single-crystal X-ray structuring supports the formation of the cocrystal of 5 with 3,5-diamino-1,2,4-triazole, which was found to be remarkably less impact-sensitive than the azo precursor. The compounds were fully characterized using IR and multinuclear NMR spectroscopy, elemental analysis, and differential scanning calorimetry. Based on heats of formation calculated with Gaussian 03 and combined with experimentally determined densities, detonation properties of the energetic materials obtained with the EXPLO5 program identify them as potentially explosive compounds. They exhibit high density, moderate to good thermal stability, acceptable oxygen balance, reasonable heat of formation, and excellent detonation properties, which in some cases are superior to those of 1,3,5,-trinitrotriazacyclohexane (RDX).