Molecular design of nitro-oxide-substituted cycloalkane derivatives for high-energy-density materials

Abstract

High-energy-density materials in which cycloalkane hydrogens (cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, and cyclooctane) were replaced with -N-NO2 and –NO functional groups were designed and evaluated with regard to their explosive characteristics by using density functional theory calculations in combination with the Kamlet-Jacobs equations and an atoms-in-molecules analysis. Improved detonation properties with a higher sensitivity than conventional explosives such as 1,3,5-trinitro-1,3,5-triazinane and 1,3,5,7-tetranitro-1,3,5,7-tetrazocane were predicted. Interestingly, NO-substituted structures showed substantial detonation properties with very low sensitivities. This method of substituting –NO groups on cycloalkanes supplies a firm basis for further studies on the design of new explosives. Moreover, the newly found structures may be promising candidates for developing primary explosives.