Asymmetric nitrogen-rich energetic materials resulting from the combination of tetrazolyl, dinitromethyl and (1,2,4-oxadiazol-5-yl)nitroamino groups with furoxan.

Three classes of nitrogen-rich energetic compounds 7-9 (combination of tetrazolyl, dinitromethyl and furoxan), 12-17 (combination of tetrazolyl, (1,2,4-oxadiazol-5-yl)nitroamino and furoxan) and 20-22 (combination of dinitromethyl, (1,2,4-oxadiazol-5-yl)nitroamino and furoxan) were obtained by selected reactions with 3,4-dicyano-furoxan. All the new compounds were thoroughly characterized by IR, NMR [1H, 13C{1H}], elemental analysis, and differential scanning calorimetry (DSC). Compounds 7, 13, 20 and 22 were also further characterized with single-crystal X-ray diffraction studies. Heats of formation and detonation performances for nine compounds were determined using Gaussian 03 and EXPLO5 v6.01 programs, showing that 15 as a secondary explosive is superior to 1,3,5-trinitrotriazacyclohexane (RDX) and 20 is a promising green primary explosive.