Salts of 5-(5-Azido-1H-1,2,4-triazol-3-yl)tetrazol-1-ol: From Highly Sensitive Primary Explosives to Insensitive Nitrogen-Rich Salts

Several metal and nitrogen-rich salts of the recently presented 5-(5-azido-1H-1,2,4-triazol-3-yl)tetrazol-1-ol (AzTTO), including silver (1), copper(I) (2), potassium (3 and 5), cesium (4), copper(II) (6), ammonium (7 and 11), hydrazinium (8), guanidinium (9 and 12), and aminoguanidinium (10), were prepared and thoroughly characterized by IR and multinuclear (H-1, C-13, N-14) NMR spectroscopy, mass spectrometry, and differential scanning calorimetry (DSC). Additionally, the structures of 3 center dot H2O, 4, 5 center dot 3H(2)O, and 7 were determined by single-crystal X-ray diffraction. The compounds show interesting structural motifs, which were analyzed and are discussed. The sensitivities towards impact, friction, and electrostatic discharge were determined according to BAM (the German Federal Institute for Materials Research and Testing) standards, thereby revealing most of the metal salts to be highly sensitive and the nitrogen-rich salts to be mostly insensitive. Furthermore, the metal salts were tested for their ability to be primary explosives.