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Benz, Maximilian; Klapötke, Thomas M.; Krumm, Burkhard; Lommel, Marcus and Stierstorfer, Jörg (2021): Nitrocarbamoyl Azide O2NN(H)C(O)N-3: A Stable but Highly Energetic Member of the Carbonyl Azide Family Maximilian. In: Journal of the American Chemical Society, Vol. 143, No. 3: pp. 1323-1327

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Abstract

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.

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