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

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 degrees C and a detonative decomposition point at 83 degrees 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.

Automated summary

The diazotization of nitrosemicarbazide led to the formation and isolation of nitrocarbamoyl azide, which exhibited surprising stability, reactivity, and sensitivity, with a melting point at 72 degrees C and a detonative decomposition point at 83 degrees C. Five selected salts were synthesized and the decomposition mechanism of nitrocarbamoyl azide in solution was investigated, clarifying its properties through experiments with methanol and hydrazine as trapping reagents. The energetic and physicochemical properties of these compounds were investigated and categorized.