Energetic Nitrogen-Rich Salts of 1-(2-Hydroxyethyl)-5-nitriminotetrazole

1-(2-Hydroxyethyl)-5-nitriminotetrazole (2) was formed by the reaction of 5-amino-1-(2-hydroxyethyl)tetrazole (1) and 100% HNO3. Compound 1 was obtained by alkylation of 5-amino-1H-tetrazole with 2-chloroethanol. Nitrogen-rich salts such as the ammonium (3), hydroxylammonium (4), guanidinium (5), aminoguanidinium (6), diaminoguanidinium (7), triaminoguanidinium (8), azidoformamidinium (9), and diaminouronium (10) 1-(2-hydroxyethyl)-5-nitriminotetrazolate were prepared by deprotonation or metathesis reactions. Compounds 3-10 were fully characterized by single-crystal X-ray diffraction (except for 9 and 10), vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis, and differential scanning calorimetry (DSC) measurements. The heats of formation of 4-10 were calculated by the atomization method based on CBS-4M enthalpies. With these values and the X-ray densities, several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code. In addition their sensitivities towards impact, friction, and electrical discharge were tested using a BAM drophammer, a friction tester, and a small-scale electrical discharge device.