Molecule Design and Properties of Cyclic Energetic Materials Based on Nitroguanidine and 1,1-Diamino-2,2-Dinitroethene

Abstract

A series of cyclic energetic derivatives based on nitroguanidine and 1,1-diamino-2,2-dinitroethene were theoretically designed. The spatial structures, infrared spectrometry, heats of formation, electronic structures, detonation properties, and thermal stabilities of these designed compounds were fully investigated by density functional theory. It is found that all the designed compounds have moderate stabilities (bond dissociation energies range from 11.3 to 99.0 kJ mol-1), high crystal densities (from 1.9589 to 2.00188 g cm-3), high positive heats of formation (from 649.6 to 1060.8 kJ mol-1) and high positive heats of detonation (from 1074.77 to 1332.06 cal g-1) which lead to the excellent detonation properties (detonation velocities range from 8.71 to 9.05 km s-1 while detonation pressures range from 35.47 to 38.55 GPa). Electronic structures such as electrostatic potentials on the surface, electronic densities, highest occupied molecular orbitals, lowest unoccupied molecular orbitals and their energy gaps were also simulated to give a better understanding of chemical and physical properties of these compounds. All the data may shine lights on the explosive searching and synthesis.

Tandem Radical Fragmentation/Cyclization of Guanidinylated Monosaccharides Grants Access to Medium-Sized Polyhydroxylated Heterocycles

“…The guanidine functional group is a structural motif frequently found in marine natural products that provides them with potent biological activities . In fact, the interest in this type of compounds has increased dramatically in recent years, as it has been shown that the incorporation of this moiety into a given molecule can lead to a wide diversity of applications, among which the development of new drugs, organocatalysts, and even new molecular materials can be highlighted. The most remarkable natural compounds within this group are those presenting a cyclic guanidinium, such as saxitoxin ( I ), tetrodotoxin ( II ), or crambescin A ( III ) (Figure ).…”