N-Oxides light up energetic performances: synthesis and characterization of dinitraminobisfuroxans and their salts

Abstract

4,4′-Diamino-[3,3′-bi(1,2,5-oxadiazole)]-5,5′-dioxide and 4,4′-diamino-[3,3′-bi(1,2,5-oxadiazole)]-2,2′-dioxide were nitrated in 100% HNO₃ at −10 °C to give 4,4′-dinitramino-[3,3′-bi(1,2,5-oxadiazole)]-5,5′-dioxide (3) and 4,4′-diamino-[3,3′-bi(1,2,5-oxadiazole)]-2,2′-dioxide (4). Nine nitrogen-rich salts were prepared and were characterized by infrared and multinuclear NMR spectroscopy, elemental analysis, differential scanning calorimetry (DSC) and X-ray single crystal diffraction in some cases. Their detonation properties were evaluated by EXPLO 5 code using the measured density and calculated heat of formation. The sensitivities were determined by standard BAM methods. Several of the new molecules exhibit detonation and other properties which compete with or exceed those of HMX.