Comparative research on promising energetic 1,3-diazinane and 1,3-oxazinane structures

Abstract

The additional carbon centers in 1,3-diazinane and 1,3-oxazinane enable them to covalently bonded geminal-explosophoric groups, leading to unique energetic properties when compared with their homologous energetic structure like RDX. In this paper, a concise synthesis and comparative studies towards 1,3,5-(trinitro1,3-diazinane-5-yl) methyl nitrate and (3,5-dinitro-1,3-oxazinan-5-yl) methyl nitrate (TNOP), two energetic 1,3-diazinane/1,3-oxazinane based promising explosive molecules, are reported. The new germinal nitro/nitroxy explosophoric moieties in the 1,3-diazinane and 1,3-oxazinane frameworks lead to novel structural and energetic properties, which have been investigated through both experimental and computational methods. Densities of the obtained compounds are 1.83 g·cm−3 and 1.72 g·cm−3, respectively, along with the detonation velocities of 8714 m·s−1 and 8112 m·s−1. The energetic properties of TNNP are comparable to those of RDX. Meanwhile, the low melting point (105 °C) and excellent insensitivity (IS﹥60 J, FS﹥360 N) of TNOP make it an ideal material for the preparation of melt-cast explosives.