Nitrogen-Rich Salts Based on Energetic Nitroaminodiazido[1,3,5]triazine and Guanazine

Highly dense nitrogen-rich ionic compounds are potential high-performance energetic materials for use in military and industrial venues. Guanazinium salts with promising energetic anions and a family of energetic salts based on nitrogen-rich cations and the 6-nitroamino-2,4-diazido[1,3,5]-triazine anion (NADAT) were prepared and fully characterized by elemental analysis, IR spectroscopy, H-1 NMR and C-13 NMR spectroscopy, and differential scanning calorimetry (DSC). The crystal structures of neutral NADAT (2) and its biguanidinium salt 5 were determined by single-crystal X-ray diffraction (2: orthorhombic, Pnma; 5: monoclinic, P2(1)). Additionally, the isomerization behavior of 2 in solution was investigated by proton-decoupled C-13 and N-15 NMR spectroscopy. All the new salts exhibit desirable physical properties, such as relatively high densities (1.63-1.78 gcm(-3)) and moderate thermal stabilities (T-d = 130-196 degrees C for 3-10 and 209-257 degrees C for 11-15). Theoretical performance calculations (Gaussian 03 and Cheetah 5.0) gave detonation pressures and velocities for the ionic compounds 3-15 in the range of 21.0-30.3 GPa and 7675-9048 ms(-1), respectively, which makes them competitive energetic materials.