Molecular design of new nitramine explosives: 1,3,5,7-tetranitro-8-(nitromethyl)-4-imidazolino[4,5-b]4-imidazolino-[4,5-e] pyridine and its N-oxide.

Hui Liu, Hongchen Du, Guixiang Wang, Yan Liu, Xuedong Gong

Department of Chemistry, Nanjing University of Science and Technology, Nanjing 210094, China. lhgbx@yahoo.com.cn

Journal of molecular modeling 2012 Apr

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Two new nitramine compounds containing pyridine, 1,3,5,7-tetranitro-8-(nitromethyl) -4-imidazolino[4,5-b]4-imidazolino-[4,5-e]pyridine and its N-oxide 1,3,5,7-tetranitro-8- (nitromethyl)-4-imidazolino[4,5-b]4-imidazolino-[4,5-e]pyridine-4-ol were proposed. Density functional theory (DFT) has been employed to study the molecular geometries, electronic structures, infrared spectra, and thermodynamic properties at the B3LYP/6-31G* level. Their detonation performances evaluated using the Kamlet-Jacobs equations with the calculated densities and heats of formation are superior to those of HMX. The predicted densities of them were ca. 2 g cm(-3), detonation velocities were over 9 km s(-1), and detonation pressures were about 40 GPa, showing that they may be potential candidates of high energy density materials (HEDMs). The natural bond orbital analysis indicated that N-NO(2) bond is the trigger bond during thermolysis process. The stability of the title compounds is slightly lower than that of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12- hexaazaisowurtzitane (CL-20). The results of this study may provide basic information for the molecular design of new HEDMs.

Citation

Hui Liu, Hongchen Du, Guixiang Wang, Yan Liu, Xuedong Gong. Molecular design of new nitramine explosives: 1,3,5,7-tetranitro-8-(nitromethyl)-4-imidazolino[4,5-b]4-imidazolino-[4,5-e] pyridine and its N-oxide. Journal of molecular modeling. 2012 Apr;18(4):1325-31