Highly energetic 1‐(azidomethyl)‐5H‐tetrazole (AzMT, 3) has been synthesized and characterized. This completes the series of 1‐(azidoalkyl)‐5H‐tetrazoles represented by 1‐(azidoethyl)‐5H‐tetrazole (AET) and 1‐(azidopropyl)‐5H‐tetrazole (APT). AzMT was thoroughly analyzed by single‐crystal X‐ray diffraction experiments, elemental analysis, IR spectroscopy and multinuclear (1H, 13C, 14N, 15N) NMR measurements. Several energetic coordination compounds (ECCs) of 3d metals (Mn, Fe, Cu, Zn) and silver in combination with anions such as (per)chlorate, mono‐ and dihydroxy‐trinitrophenolate were prepared, giving insight into the coordination behavior of AzMT as a ligand. The synthesized ECCs were also analyzed by X‐ray diffraction experiments, elemental analysis, and IR spectroscopy. Differential thermal analysis for all compounds was conducted, and the sensitivity towards external stimuli (impact, friction, and ESD) was measured. Due to the high enthalpy of formation of AzMT (+654.5 kJ mol−1), some of the resulting coordination compounds are extremely sensitive, yet are able to undergo deflagration‐to‐detonation transition (DDT) and initiate pentaerythritol tetranitrate (PETN). Therefore, they are to be ranked as primary explosives.
For the first time,
the highly sensitive 1-(nitratomethyl)-5H-tetrazole
(1-NAMT) was synthesized, representing the shortest
possible 1-(nitratoalkyl)-5H-tetrazole with a combined
nitrogen and oxygen content of 81.4%. Compared to its related ethyl
derivative, 1-(nitratoethyl)-5H-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 (e.g., nitrate, chlorate, and perchlorate) and nitroaromatic
anions (e.g., picrate and styphnate) were synthesized
and thoroughly analyzed. It is shown that the formation of ECCs with
nitroaromatic anions (T
dec ∼ 180
°C) is a suitable strategy to improve the rather low thermal
stability of 1-NAMT (125 °C).
N-Hydroxymethylation of heterocyclic compounds offers a promising starting procedure to ultimetly introduce nitratomethyl- as well as azidomethyl- moieties. Applied to 5,5’-bistetrazole, the resulting 2,2’-di(azidomethyl)bistetrazole (3) and 2,2’-di(nitratomethyl)bistetrazole (4) are high-performing...
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