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Issue 6, 2018
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Preparation and characteristics of 1,2,4-oxadiazole-derived energetic ionic salts with nitrogen linkages

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Abstract

A new family of energetic ionic salts containing a 1,2,4-oxadiazole ring and an amino or triazene linkage were synthesized by the oxidation of 3-nitro-5-amino-1,2,4-oxadiazole (NOA) with sodium dichloroisocyanurate (SDCI) affording sodium bis(3-nitro-1,2,4-oxadiazol-5-yl)amide (2) and sodium 1,3-bis(3-nitro-1,2,4-oxadiazol-5-yl)triaz-2-en-1-ide (3) followed by cation metathesis. Their molecular structures were fully characterized by 1H and 13C NMR, MS and IR spectroscopy, while three ionic salts 4, 5 and 7 along with two sodium salt precursors 2 and 3 were confirmed by single-crystal X-ray diffraction. Differential scanning calorimetry (DSC) was employed to investigate the thermal stability of these ionic salts, revealing moderate onset decomposition temperatures ranging from 166 °C to 249 °C. By using a fall hammer test, most salts were found to exhibit low impact sensitivities. Guanidinium bis(3-nitro-1,2,4-oxadiazol-5-yl)amide (4) exhibits good performance with acceptable detonation properties (D: 8351 m s−1, P: 29.0 GPa), good stability (Td: 241 °C, onset) and low impact sensitivity (IS > 40 J).

Graphical abstract: Preparation and characteristics of 1,2,4-oxadiazole-derived energetic ionic salts with nitrogen linkages

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Publication details

The article was received on 17 Sep 2017, accepted on 28 Jan 2018 and first published on 29 Jan 2018


Article type: Paper
DOI: 10.1039/C7NJ03548A
Citation: New J. Chem., 2018,42, 4036-4044
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    Preparation and characteristics of 1,2,4-oxadiazole-derived energetic ionic salts with nitrogen linkages

    F. Pang, G. Wang, T. Lu, G. Fan and F. Chen, New J. Chem., 2018, 42, 4036
    DOI: 10.1039/C7NJ03548A

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