Promising hydrazinium 3-Nitro-1,2,4-triazol-5-one and its analogs

Twelve salts of 3-nitro-1,2,4-triazol-5-one (NTO) (ammonium, hydrazinium, guanidinium, aminoguanidinium, diaminoguanidinium, triaminoguanidinium, N-carbamoylguanidinium, semicarbazidium, 1,5-diamino-1,2,4-tetrazolium, 3,4,5- triamino-1,2,4-triazolium, 3,6,7-triamino-7H-[1, 2, 4]triazolo[5,1-c][1,2,4]triazol-2- ium, and 4,4′,5,5′-tetraamino-3,3′-bi-1,2,4-triazolium) were synthesized. The new salts were fully characterized by 1H and 13C NMR spectroscopy, infrared spectroscopy, and elemental analysis. The crystal structures of salts 10 and 11 were determined by single-crystal X-ray diffraction. All energetic salts except salt 6 exhibit excellent thermal stabilities with decomposition temperatures ranging from 203 to 270 °C. The densities of salts ranged from 1.65 to 1.88 g cm−1 as measured by a gas pycnometer. Theoretical performance calculations (Gaussian 03 and EXPLO5 v6.01) yielded detonation pressures and detonation velocities for the energetic salts, ranging from 24.4 to 38.1 GPa and 8136 to 9575 m s−1, respectively. In particular, salt 2 has an outstanding detonation performance (P cj = 38.1 GPa, v D = 9575 m s−1) with a satisfactory acidity compared to that of NTO (pK a = 5.63 versus pK a = 2.37). Furthermore, the particles of salt 2 form two-dimensional blades of submicron size, as determined by scanning electron microscopy analysis. Meanwhile, salt 2 was compatible with TNAZ, TATB, TKX-50, Al, NH4ClO4, CL-20, TNT, and F2603 fluororubber, as determined by differential scanning calorimetry or vacuum stability tests.