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Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives

Larin A.A., Bystrov D.M., Fershtat L.L., Konnov A.A., Makhova N.N., Monogarov K.A., Meerov D.B., Melnikov I.N., Pivkina A.N., Kiselev V.G., Muravyev N.V.
Тип документаJournal Article
Дата публикации2020-12-10
Название журналаMolecules
ИздательMultidisciplinary Digital Publishing Institute (MDPI)
  • Organic Chemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Pharmaceutical Science
  • Molecular Medicine
  • Analytical Chemistry
  • Chemistry (miscellaneous)
Краткое описание

In the present work, we studied in detail the thermochemistry, thermal stability, mechanical sensitivity, and detonation performance for 20 nitro-, cyano-, and methyl derivatives of 1,2,5-oxadiazole-2-oxide (furoxan), along with their bis-derivatives. For all species studied, we also determined the reliable values of the gas-phase formation enthalpies using highly accurate multilevel procedures W2-F12 and/or W1-F12 in conjunction with the atomization energy approach and isodesmic reactions with the domain-based local pair natural orbital (DLPNO) modifications of the coupled-cluster techniques. Apart from this, we proposed reliable benchmark values of the formation enthalpies of furoxan and a number of its (azo)bis-derivatives. Additionally, we reported the previously unknown crystal structure of 3-cyano-4-nitrofuroxan. Among the monocyclic compounds, 3-nitro-4-cyclopropyl and dicyano derivatives of furoxan outperformed trinitrotoluene, a benchmark melt-cast explosive, exhibited decent thermal stability (decomposition temperature >200 °C) and insensitivity to mechanical stimuli while having notable volatility and low melting points. In turn, 4,4′-azobis-dicarbamoyl furoxan is proposed as a substitute of pentaerythritol tetranitrate, a benchmark brisant high explosive. Finally, the application prospects of 3,3′-azobis-dinitro furoxan, one of the most powerful energetic materials synthesized up to date, are limited due to the tremendously high mechanical sensitivity of this compound. Overall, the investigated derivatives of furoxan comprise multipurpose green energetic materials, including primary, secondary, melt-cast, low-sensitive explosives, and an energetic liquid.

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1. Larin A.A. и др. Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives // Molecules. 2020. Т. 25. № 24. С. 5836.


DO - 10.3390/molecules25245836

UR -

TI - Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives

T2 - Molecules

AU - Larin, Alexander A.

AU - Bystrov, Dmitry M.

AU - Fershtat, Leonid L.

AU - Konnov, Alexey A.

AU - Makhova, Nina N.

AU - Monogarov, Konstantin A.

AU - Meerov, Dmitry B.

AU - Melnikov, Igor N.

AU - Pivkina, Alla N.

AU - Kiselev, Vitaly G.

AU - Muravyev, Nikita V.

PY - 2020

DA - 2020/12/10


SP - 5836

IS - 24

VL - 25

SN - 1420-3049

ER -

BibTex |


doi = {10.3390/molecules25245836},

url = {},

year = 2020,

month = {dec},

publisher = {{MDPI} {AG}},

volume = {25},

number = {24},

pages = {5836},

author = {Alexander A. Larin and Dmitry M. Bystrov and Leonid L. Fershtat and Alexey A. Konnov and Nina N. Makhova and Konstantin A. Monogarov and Dmitry B. Meerov and Igor N. Melnikov and Alla N. Pivkina and Vitaly G. Kiselev and Nikita V. Muravyev},

title = {Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives}


Larin, Alexander A. et al. “Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives.” Molecules 25.24 (2020): 5836. Crossref. Web.