School of Chemistry and Materials Science, Guizhou Education University, Guiyang, 051008, China.
J Mol Model. 2019 Sep 3;25(9):298. doi: 10.1007/s00894-019-4190-5.
A series of nitro-imidazole derivatives were designed by replacing hydrogen atoms on imidazole ring with nitro group one by one. In order to investigate the thermodynamic stability, heat of formation (HOF), and bond dissociation energy (BDE) are calculated at the B3PW91/6-311+G(d,p) level. In order to investigate the impact sensitivity and detonation property, the drop height (H), free space per molecule in crystal lattice (ΔV), detonation velocity (D), and detonation pressure (P) are calculated by using the empirical Kamlet-Jacobs (K-J) equation. The results show that the thermal stabilities of title molecules are determined by whether nitro group is associated to 1-position or not and accompanied with the steric hindrance between nitro groups and the charge population on the carbon atoms of imidazole ring. The excellent impact sensitivity and detonation performance of title molecules are also evaluated. On the consideration both of stability and detonation characters, 2,4,5-trinitro-1H-imidazole (D = 8.98 km/s, P = 36.70 GPa) is screened out as the potential high-energy-density molecule for further research.
设计了一系列硝基亚唑衍生物，方法是将亚唑环上的氢原子逐个用硝基取代。为了研究热力学稳定性，在 B3PW91/6-311+G(d,p)水平下计算了生成热（HOF）和键离解能（BDE）。为了研究撞击感度和爆轰性能，使用经验性的 Kamlet-Jacobs（K-J）方程计算了落高（H）、晶格中每个分子的自由空间（ΔV）、爆速（D）和爆压（P）。结果表明，标题分子的热稳定性取决于硝基是否与 1 位相连，以及硝基之间的空间位阻和咪唑环碳原子上的电荷分布。还评估了标题分子的优异撞击感度和爆轰性能。在考虑稳定性和爆轰特性的基础上，筛选出 2,4,5-三硝基-1H-咪唑（D = 8.98 km/s，P = 36.70 GPa）作为具有进一步研究潜力的潜在高能密度分子。
