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Molecules

Title:		"Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives"
Author(s):		Larin AA; Bystrov DM; Fershtat LL; Konnov AA; Makhova NN; Monogarov KA; Meerov DB; Melnikov IN; Pivkina AN; Kiselev VG; Muravyev NV;
Address:		"Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Avenue, 119991 Moscow, Russia. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, 4 Kosygina Street, 119991 Moscow, Russia. Novosibirsk State University, 1 Pirogova Street, 630090 Novosibirsk, Russia. Institute of Chemical Kinetics and Combustion SB RAS, 3 Institutskaya Street, 630090 Novosibirsk, Russia"
Journal Title:		Molecules
Year:		2020
Volume:		20201210
Issue:		24
Page Number:		-
DOI:		10.3390/molecules25245836
ISSN/ISBN:		1420-3049 (Electronic) 1420-3049 (Linking)
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 degrees 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"
Keywords:		"Calorimetry, Differential Scanning Chemical Phenomena Chemistry Techniques, Synthetic Explosive Agents/*chemistry Isomerism Models, Molecular Molecular Conformation Molecular Structure Nitro Compounds/chemical synthesis/chemistry Oxadiazoles/chemical synt;"
Notes:		"MedlineLarin, Alexander A Bystrov, Dmitry M Fershtat, Leonid L Konnov, Alexey A Makhova, Nina N Monogarov, Konstantin A Meerov, Dmitry B Melnikov, Igor N Pivkina, Alla N Kiselev, Vitaly G Muravyev, Nikita V eng 19-73-20217/Russian Science Foundation/ Switzerland 2020/12/17 Molecules. 2020 Dec 10; 25(24):5836. doi: 10.3390/molecules25245836"