Open Access
Molecules, volume 25, issue 24, pages 5836
Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives
Bystrov Dmitry M.
1
,
Konnov Alexey A
1
,
Makhova Nina N
1
,
Monogarov Konstantin A
2
,
Meerov Dmitry B
2
,
Melnikov Igor N
2
,
Pivkina Alla
2
,
Kiselev Vitaly G
2, 3, 4
,
Publication type: Journal Article
Publication date: 2020-12-10
PubMed ID:
33322001
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
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.
Citations by journals
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ACS Omega
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1 publication, 5.56%
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Citations by publishers
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3
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6
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6 publications, 33.33%
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Wiley
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Larin A. A. et al. Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives // Molecules. 2020. Vol. 25. No. 24. p. 5836.
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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., Kiselev V. G., Muravyev N. Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives // Molecules. 2020. Vol. 25. No. 24. p. 5836.
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TY - JOUR
DO - 10.3390/molecules25245836
UR - https://doi.org/10.3390%2Fmolecules25245836
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
AU - Kiselev, Vitaly G
AU - Muravyev, Nikita
PY - 2020
DA - 2020/12/10 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 5836
IS - 24
VL - 25
PMID - 33322001
SN - 1420-3049
ER -
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@article{2020_Larin,
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 Pivkina and Vitaly G Kiselev and Nikita Muravyev},
title = {Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives},
journal = {Molecules},
year = {2020},
volume = {25},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {dec},
url = {https://doi.org/10.3390%2Fmolecules25245836},
number = {24},
pages = {5836},
doi = {10.3390/molecules25245836}
}
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Larin, Alexander A., et al. “Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives.” Molecules, vol. 25, no. 24, Dec. 2020, p. 5836. https://doi.org/10.3390%2Fmolecules25245836.