Synthesis and investigation of 5-amino-2,4,6-trinitrobenzene-1,3-diol and its salts

5-amino-2,4,6-trinitrobenzene-1,3-diol (ATNBD) was synthesized using an improved literature method. The reactions of ATNBD with different N-bases (e.g., ammonia, hydrazine, hydroxylamine, and guanidine) and metathesis reactions producing energetic salts were reported. Several energetic compounds were synthesized and characterized for the first time using multinuclear NMR spectroscopy, mass spectrometry, elemental analysis, and differential scanning calorimetry (TG-DSC). The crystal structures of ATNBD and three energetic salts were determined using single-crystal X-ray diffraction at room temperature. Heats of formation (HOF) for the metal-free species were calculated using the Gaussian 09 software. Detonation parameters were estimated using the EXPLO5 program. The sensitivities toward impact and friction were also determined. Energetic evaluation indicates that, in addition to the molecular ATNBD, some ionic derivatives, 3, 4, 5, and 9, also have high densities (1.79-1.88 g cm-3), good detonation pressures, and velocities (P, 31.5-38.8 GPa; vD, 8450-9097 m s-1), as well as acceptable impact and friction sensitivities (IS, 5-42 J; FS, 120-360 N). These attractive features highlight the application potential of the salts of 3, 4, and 9.