Synthesis, Structure and Energetic Properties of a Catenated N6, Polynitro Compound: 1,1’-Azobis(3,5-dinitropyrazole)

A nitrogen-rich, polynitro energetic compound with an N,N-azo linkage, 1,1’-azobis(3,5-dinitropyrazole) (ABDNP), has been synthesized by an oxidative coupling reaction of 1-amino-3,5-dinitropyrazole with different oxidizing agents. The target compound was characterized by IR spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopy, elemental analysis, mass spectra, X-ray diffraction and differential scanning calorimetry (DSC). The DSC results show that 1,1’-azobis(3,5-dinitropyrazole) decomposes at a relatively high onset temperature (202.9 °C), which indicates that 1,1’-azobis(3,5-dinitropyrazole) has acceptable thermal stability. The energetic properties were obtained, with a measured density and heat of formation matched by theoretically computed values based on the B3LYP method.