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, 1 H NMR and 13 C 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, P 2 1 ). Additionally, the isomerization behavior of 2 in solution was investigated by proton‐decoupled 13 C and 15 N NMR spectroscopy. All the new salts exhibit desirable physical properties, such as relatively high densities (1.63–1.78 g cm −3 ) and moderate thermal stabilities ( T d = 130–196 °C for 3 – 10 and 209–257 °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 m s −1 , respectively, which makes them competitive energetic materials.