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

RAS - Zelinsky Institute of Organic Chemistry
RAS - Kurnakov Institute of General and Inorganic Chemistry
RAS - A.N. Nesmeyanov Institute of Organoelement Compounds
Mendeleev University of Chemical Technology
RAS - N.N. Semenov Institute of Chemical Physics

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

24 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

Cite this

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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year = "2022",

month = sep,

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

language = "English",

volume = "3",

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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

UR - https://www.scopus.com/pages/publications/85136552520

U2 - 10.1016/j.enmf.2022.08.002

DO - 10.1016/j.enmf.2022.08.002

M3 - Article

AN - SCOPUS:85136552520

SN - 2666-6472

VL - 3

SP - 146

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JO - Energetic Materials Frontiers

JF - Energetic Materials Frontiers

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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