Trinitromethyl Energetic Groups Enhance High Heats of Detonation

The introduction of groups with high enthalpies of formation can effectively improve the detonation performance of the compounds. A series of novel energetic compounds (10–13) with high enthalpies of formation, high density, and high nitrogen–oxygen content were designed and synthesized by combining gem-polynitromethyl, 1,2,4-oxadiazole, furoxan, and azo groups. All the new compounds were thoroughly characterized by IR, NMR, elemental analysis, and differential scanning calorimetry. Compounds 10 and 11 were also further characterized with single-crystal X-ray diffraction. Compound 11 has high density (1.93 g cm–3), high enthalpy of formation (993.5 kJ mol–1), high detonation velocity (9411 m s–1), and high heat of detonation (6889 kJ kg–1) and is a potentially excellent secondary explosive.