Nitrocarbamoyl Azide O2NN(H)C(O)N3: A Stable but Highly Energetic Member of the Carbonyl Azide Family

The diazotization of nitrosemicarbazide (1) resulted in the formation and isolation of nitrocarbamoyl azide (2), which was thoroughly characterized by spectroscopic and structural methods. This compound shows surprising stability but also high reactivity and sensitivity, with a melting point of 72 °C and a detonative decomposition point at 83 °C. In addition, five selected salts were synthesized by careful deprotonation. The decomposition mechanism of 2 in solution was investigated and could be clarified by performing experiments using methanol and hydrazine as trapping reagents. The energetic and physicochemical properties of all these compounds were investigated and classified.