Unusual Energetic Periodate, Sulfate and Amino‐bistetrazolate Salts of the Trinitropropylammonium Cation

Starting from a nucleophilic Michael addition of nitroform to acrylamide, three synthetic strategies towards 1,1,1‐trinitropropyl‐1‐ammonium salts are described. Due to the high oxygen content and density of one periodate salt, its suitability as high‐energy dense oxidizer in energetic formulations was predicted according to its specific impulse and detonation velocity. Furthermore, those properties were compared to the nitrogen‐rich amino‐bis(5‐tetrazolate) salt. The parameters were calculated with the EXPLO5 (V6.03) computer code and compared to the common solid rocket propellant ammonium perchlorate (AP). Calculations towards the energies of formation were performed using Gaussian 09. Characterization including multinuclear NMR spectroscopy, vibrational analysis (IR, Raman) as well as elemental analysis and a single‐crystal X‐ray diffraction study was performed. The thermal stability was studied using differential scanning calorimetry and the sensitivities against impact and friction were determined