Oxatriazoles: Potential Frameworks for Energetic Compounds?

Abstract Fourteen oxatriazoles have been investigated computationally as potential energetic compounds. They include the two isomeric parent compounds, their amino and nitro derivatives, four N ‐oxides and four amino‐ N ‐oxides. Densities and solid state heats of formation were calculated for all of these compounds, and used to determine their detonation velocities and detonation pressures by means of the Kamlet‐Jacobs equations. Four of the compounds, all N ‐oxides, surpass or essentially equal Klapötke's criteria for detonation velocity and detonation pressure. Three other N ‐oxides meet just the detonation velocity criterion. Impact sensitivity was addressed in terms of three factors that are known to affect it: the free space per molecule in the crystal lattice, the electrostatic potential on the molecular surface, and the detonation heat release of the compound. Three of the N ‐oxides with the highest detonation velocities and detonation pressures have undesirably large heats of detonation, a warning of possible impact sensitivity. However 5‐amino‐1,2,3,4‐oxatriazole‐3‐oxide combines good detonation properties with a moderate heat release; its free space per molecule in the crystal lattice and molecular surface electrostatic potential are also consistent with low sensitivity. Overall, we believe that the results of this work should encourage further investigation of oxatriazole derivatives as energetic compounds.