The treatment of triaminoguanidinium chloride with two equivalents of sodium nitrite under acidic conditions, followed by the cyclization with stoichiometric amounts of either sodium hydroxide solution or solid sodium carbonate yielded 1-amino-5-azidotetrazole (), 5-azido-1-diazidocarbamoyltetrazole (), and 1-(aminoazidocarbamoyl)-5-azidotetrazole (). The three novel compounds could be isolated by short-column liquid chromatography by using chloroform in reasonable yields. The mechanism of the formation as well as the decomposition pathway of the materials was investigated and a full characterization of all three compounds is presented. Compounds have been characterized by means of Raman and IR as well as multinuclear NMR spectroscopy, mass spectrometry, and X-ray diffraction studies. Thermal stabilities have been evaluated by differential scanning calorimetry. Theoretical calculations have been performed to ensure the assignment of the vibrational modes obtained from Raman and IR measurements. The sensitivity values obtained from our measurements reflect the behavior of the compounds, which show an extremely high sensitivity toward mechanical as well as thermal stimuli.
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