Simple and energetic: Novel combination of furoxan and 1,2,4-triazole rings in the synthesis of energetic materials

Alexander A. Larin; Ivan V. Ananyev; Ekaterina V. Dubasova; Fedor E. Teslenko; Konstantin A. Monogarov; Dmitry V. Khakimov; Chun lin He; Si ping Pang; Galina A. Gazieva; Leonid L. Fershtat

doi:10.1016/j.enmf.2022.08.002

Simple and energetic: Novel combination of furoxan and 1,2,4-triazole rings in the synthesis of energetic materials

Alexander A. Larin, Ivan V. Ananyev, Ekaterina V. Dubasova, Fedor E. Teslenko, Konstantin A. Monogarov, Dmitry V. Khakimov, Chun lin He, Si ping Pang, Galina A. Gazieva, Leonid L. Fershtat^*

^*Corresponding author for this work

School of Material Science and Engineering

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Two novel representatives of energetic (1,2,4-triazolyl)furoxans were prepared from the readily available (furoxanyl)amidrazones. Synthesized compounds were thoroughly characterized with IR and multinuclear NMR spectroscopy, elemental analysis and X-ray diffraction data. Analysis of structural features supported by quantum-chemical calculations revealed the main reasons for experimentally observed difference in thermal stability and mechanical sensitivity of both compounds. It was found that 3-cyano-4-(1H-1,2,4-triazol-3-yl)furoxan is more thermally stable (T_d: 229 °C) than 4-azido-3-(1H-1,2,4-triazol-3-yl)furoxan (T_d: 154 °C) and the latter compound is also more sensitive to impact and friction. In addition, both heterocyclic assemblies have high detonation parameters (v_D: 7.0–8.0 km·s⁻¹; p: 22–29 GPa) exceeding those of benchmark explosives trinitrotoluene and hexanitrostilbene which enable their usability for various energetic applications.

Original language	English
Pages (from-to)	146-153
Number of pages	8
Journal	Energetic Materials Frontiers
Volume	3
Issue number	3
DOIs	https://doi.org/10.1016/j.enmf.2022.08.002
Publication status	Published - Sept 2022

Keywords

1,2,5-Oxadiazoles
Electrostatic potential
Energetic materials
Mechanical sensitivity
Nitrogen heterocycles

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10.1016/j.enmf.2022.08.002

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Larin, A. A., Ananyev, I. V., Dubasova, E. V., Teslenko, F. E., Monogarov, K. A., Khakimov, D. V., He, C. L., Pang, S. P., Gazieva, G. A., & Fershtat, L. L. (2022). Simple and energetic: Novel combination of furoxan and 1,2,4-triazole rings in the synthesis of energetic materials. Energetic Materials Frontiers, 3(3), 146-153. https://doi.org/10.1016/j.enmf.2022.08.002

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title = "Simple and energetic: Novel combination of furoxan and 1,2,4-triazole rings in the synthesis of energetic materials",

abstract = "Two novel representatives of energetic (1,2,4-triazolyl)furoxans were prepared from the readily available (furoxanyl)amidrazones. Synthesized compounds were thoroughly characterized with IR and multinuclear NMR spectroscopy, elemental analysis and X-ray diffraction data. Analysis of structural features supported by quantum-chemical calculations revealed the main reasons for experimentally observed difference in thermal stability and mechanical sensitivity of both compounds. It was found that 3-cyano-4-(1H-1,2,4-triazol-3-yl)furoxan is more thermally stable (Td: 229 °C) than 4-azido-3-(1H-1,2,4-triazol-3-yl)furoxan (Td: 154 °C) and the latter compound is also more sensitive to impact and friction. In addition, both heterocyclic assemblies have high detonation parameters (vD: 7.0–8.0 km·s−1; p: 22–29 GPa) exceeding those of benchmark explosives trinitrotoluene and hexanitrostilbene which enable their usability for various energetic applications.",

keywords = "1,2,5-Oxadiazoles, Electrostatic potential, Energetic materials, Mechanical sensitivity, Nitrogen heterocycles",

author = "Larin, {Alexander A.} and Ananyev, {Ivan V.} and Dubasova, {Ekaterina V.} and Teslenko, {Fedor E.} and Monogarov, {Konstantin A.} and Khakimov, {Dmitry V.} and He, {Chun lin} and Pang, {Si ping} and Gazieva, {Galina A.} and Fershtat, {Leonid L.}",

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doi = "10.1016/j.enmf.2022.08.002",

language = "English",

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T2 - Novel combination of furoxan and 1,2,4-triazole rings in the synthesis of energetic materials

AU - Larin, Alexander A.

AU - Ananyev, Ivan V.

AU - Dubasova, Ekaterina V.

AU - Teslenko, Fedor E.

AU - Monogarov, Konstantin A.

AU - Khakimov, Dmitry V.

AU - He, Chun lin

AU - Pang, Si ping

AU - Gazieva, Galina A.

AU - Fershtat, Leonid L.

PY - 2022/9

Y1 - 2022/9

N2 - Two novel representatives of energetic (1,2,4-triazolyl)furoxans were prepared from the readily available (furoxanyl)amidrazones. Synthesized compounds were thoroughly characterized with IR and multinuclear NMR spectroscopy, elemental analysis and X-ray diffraction data. Analysis of structural features supported by quantum-chemical calculations revealed the main reasons for experimentally observed difference in thermal stability and mechanical sensitivity of both compounds. It was found that 3-cyano-4-(1H-1,2,4-triazol-3-yl)furoxan is more thermally stable (Td: 229 °C) than 4-azido-3-(1H-1,2,4-triazol-3-yl)furoxan (Td: 154 °C) and the latter compound is also more sensitive to impact and friction. In addition, both heterocyclic assemblies have high detonation parameters (vD: 7.0–8.0 km·s−1; p: 22–29 GPa) exceeding those of benchmark explosives trinitrotoluene and hexanitrostilbene which enable their usability for various energetic applications.

AB - Two novel representatives of energetic (1,2,4-triazolyl)furoxans were prepared from the readily available (furoxanyl)amidrazones. Synthesized compounds were thoroughly characterized with IR and multinuclear NMR spectroscopy, elemental analysis and X-ray diffraction data. Analysis of structural features supported by quantum-chemical calculations revealed the main reasons for experimentally observed difference in thermal stability and mechanical sensitivity of both compounds. It was found that 3-cyano-4-(1H-1,2,4-triazol-3-yl)furoxan is more thermally stable (Td: 229 °C) than 4-azido-3-(1H-1,2,4-triazol-3-yl)furoxan (Td: 154 °C) and the latter compound is also more sensitive to impact and friction. In addition, both heterocyclic assemblies have high detonation parameters (vD: 7.0–8.0 km·s−1; p: 22–29 GPa) exceeding those of benchmark explosives trinitrotoluene and hexanitrostilbene which enable their usability for various energetic applications.

KW - 1,2,5-Oxadiazoles

KW - Electrostatic potential

KW - Energetic materials

KW - Mechanical sensitivity

KW - Nitrogen heterocycles

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IS - 3

ER -

Simple and energetic: Novel combination of furoxan and 1,2,4-triazole rings in the synthesis of energetic materials

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Keywords

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