Theoretical investigations on the structure, density, thermodynamic and performance properties of amino-, methyl-, and nitroimidazoles and their N-oxides

Abstract

Density functional theory calculations at the B3LYP/aug-cc-pVDZ level have been performed to explore the structure, stability, heat of explosion, density, and the performance properties of amino-, methyl-, and nitroimidazoles. N-Nitroimidazoles have shown lower densities compared with those of C-nitroimidazoles. Detonation properties of title compounds were evaluated by using Kamlet–Jacob semi-empirical equations based on the predicted densities and the calculated heats of detonation. It has been found that some compounds with the calculated densities 2.0 g/cm3, detonation velocities over 9.10 km/s and detonation pressures of about 45 GPa (some even over 50 GPa) may be novel potential high energy materials. The higher performance of nitroimidazole-N-oxides is apparently due to their higher densities (2.0–2.515 g/cm3). Heat of explosion, stability, density, and performance properties are related to the number and relative positions of –NO2, –NH2, and –CH3 groups of the imidazole ring. The designed nitroimidazoles satisfy the criteria of high energy materials.