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.
Bibliographical noteFunding Information:
This work was supported by the Office of Naval Research (N00014-16-1-2089 and N00014-15-WX-0-0149) and the Defense Threat Reduction Agency (HDTRA 1-15-1-0028). We are indebted to Dr Orion Berryman (NSF CHE1337908 and CoBRE NIGMS P20GM103546) and Dr Brendan Twamley for crystal structures.
© The Royal Society of Chemistry 2016.