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 1 H and 13 C 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, NH 4 ClO 4 , CL-20, TNT, and F2603 fluororubber, as determined by differential scanning calorimetry or vacuum stability tests.