1-(Nitratomethyl)-5<i>H</i>-tetrazole: A Highly Sensitive Ligand with Improved Oxygen Balance for Laser-Ignitable Coordination Compounds

Abstract

For the first time, the highly sensitive 1-(nitratomethyl)-5<i>H</i>-tetrazole (1-NAMT) was synthesized, representing the shortest possible 1-(nitratoalkyl)-5<i>H</i>-tetrazole with a combined nitrogen and oxygen content of 81.4%. Compared to its related ethyl derivative, 1-(nitratoethyl)-5<i>H</i>-tetrazole, it exhibits improved oxygen balance, resulting in higher detonation parameters. 1-NAMT was thoroughly analyzed by single-crystal diffraction experiments accompanied by elemental analysis, IR spectroscopy, and multinuclear (¹H, ¹³C, and ¹⁴N) NMR measurements. The thermal behavior of 1-NAMT was analyzed by differential thermal analysis supported by thermogravimetric analysis. Furthermore, energetic coordination compounds (ECCs) of Cu with different inorganic (<i>e.g.</i>, nitrate, chlorate, and perchlorate) and nitroaromatic anions (<i>e.g.</i>, picrate and styphnate) were synthesized and thoroughly analyzed. It is shown that the formation of ECCs with nitroaromatic anions (<i>T</i>_dec ∼ 180 °C) is a suitable strategy to improve the rather low thermal stability of 1-NAMT (125 °C).