Synthesis of high-performance insensitive energetic materials based on nitropyrazole and 1,2,4-triazole?

New Journal of Chemistry Pub Date: 2019-06-14 DOI: 10.1039/C9NJ01445D

Abstract

A new family of symmetric (4-nitro-1H-pyrazole-3,5-diyl)bis(1H-1,2,4-triazole)-based derivatives were obtained. All these new compounds were characterized by (1H, 13C)NMR spectroscopy, infrared spectroscopy, elemental analysis and differential scanning calorimetry (DSC). The structures of 5,5′-(4-nitro-1H-pyrazole-3,5-diyl)bis(3-nitro-1H-1,2,4-triazole) (6) and N,N′-((4-nitro-1H-pyrazole-3,5-diyl)bis(1H-1,2,4-triazole-5,3-diyl))dinitramide (7) were further confirmed by single crystal X-ray diffraction. In addition, the theoretical calculations by using the Gaussian 09 package show that target compounds have high heats of formation ranging from 1.40 to 2.84 kJ g?1. Among them, the safety and detonation performances of 6 (D: 8747 m s?1, P: 33.0 GPa, Td: 238.2 °C, IS: 30 J) and energetic salts dihydroxylammonium((4-nitro-1H-pyrazole-3,5-diyl)bis(1H-1,2,4-triazole-5,3-diyl))bis(nitroamide) (9) (D: 9077 m s?1, P: 33.6 GPa, IS: >40 J) and dihydrazinium((4-nitro-1H-pyrazole-3,5-diyl)bis(1H-1,2,4-triazole-5,3-diyl))bis(nitroamide) (10) (D: 8759 m s?1, P: 30.2 GPa, IS: >40 J) are comparable to those of 1,3,5-trinitroperhydro-1,3,5-triazine (RDX: D = 8795 m s?1, P = 34.9 GPa, Td = 210 °C, IS: 7.4 J) due to the positive effect of ternary hydrogen bonds.

Graphical abstract: Synthesis of high-performance insensitive energetic materials based on nitropyrazole and 1,2,4-triazole
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