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^*

^*此作品的通讯作者

材料学院

科研成果: 期刊稿件 › 文章 › 同行评审

18 引用（Scopus）

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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.

源语言	英语
页（从-至）	146-153
页数	8
期刊	Energetic Materials Frontiers
卷	3
期	3
DOI	https://doi.org/10.1016/j.enmf.2022.08.002
出版状态	已出版 - 9月 2022

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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.}",

note = "Publisher Copyright: {\textcopyright} 2022 The Authors",

year = "2022",

month = sep,

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

language = "English",

volume = "3",

pages = "146--153",

journal = "Energetic Materials Frontiers",

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T1 - Simple and energetic

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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U2 - 10.1016/j.enmf.2022.08.002

DO - 10.1016/j.enmf.2022.08.002

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JF - Energetic Materials Frontiers

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ER -

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

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