Bis(3-(trinitromethyl)-1H-1,2,4-triazol-5-yl)methanone: A mildly acidic high-performing energetic material

Abstract

High performance, acceptable thermostability, and low mechanical sensitivity are high-demand properties in the design of competitive materials. Nitrogen-rich compounds are an alternative source of green molecules. Two simple, efficient synthetic routes to a novel material, bis (3-(trinitromethyl) − 1H-1,2,4-triazol-5-yl) methanone, 5, by using inexpensive starting compounds are described. Compound 5 has interesting chemical reactivity with water in the presence of organic solvents to form a gem diol of bis (3-(trinitromethyl) − 1H-1,2,4-triazol-5-yl) methanediol, 5a. All new molecules are well characterized by advanced spectroscopic techniques. The structures of 5·Et2O, 5a·3H2O, and salt 6 are confirmed by single-crystal X-ray analysis. The densities of the solid powder compound 5, and the crystals of 5a·3H2O were measured by a gas pycnometer. The theoretical densities and Explo5 calculations of solvent-free molecules, 5 and 5a, suggest that expanding the functionality of carbonyl-bridged compounds may be an alternative way to achieve high-performing materials.