Impact of regiochemistry in energetic materials science: a case of (nitratomethyl-1,2,3-triazolyl)furazans

Impact of regiochemistry in energetic materials science: a case of (nitratomethyl-1,2,3-triazolyl)furazans Full article

Journal

Dalton Transactions
ISSN: 1477-9234 , E-ISSN: 1477-9226

Output data

Year: 2023, Volume: 52, Number: 22, Pages: 7673-7683 Pages count : 11 DOI: 10.1039/d3dt00917c

Authors

Epishina Margarita ¹ , Kulikov Alexander ¹ , Ananyev Ivan V. ^2,3 , Anisimov Aleksei A. ^3,4 , Monogarov Konstantin Alexandrovich ⁵ , Fershtat Leonid ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, Moscow 119991, Russian Federation
2	N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, GSP-1, Leninsky prospect, 31, 119991 Moscow, Russia
3	National Research University Higher School of Economics 101000, Myasnitskaya str., 20, Moscow, Russian Federation
4	Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova st, Moscow, 119991, Russia
5	N. N. Semenov Federal Research Centre for Chemical Physics, Russian Academy of Sciences, 4 Kosygin Str., Moscow 119991, Russian Federation

The preparation of multipurpose high-energy materials for space technologies remains a challenging task and such materials usually require special precautions and fine tunability of their functional properties. To unveil new opportunities en route to high-performance energetic materials, novel potential melt-castable explosives and energetic plasticizers incorporating a (1,2,3-triazolyl)furazan scaffold enriched with nitro and nitratomethyl explosophoric functionalities were synthesized. The successful implementation of the regiodivergent approach enabled the preparation of regioisomeric (nitratomethyltriazolyl)furazans that possessed significantly different physicochemical properties classifying the target materials as melt-castable substances or energetic plasticizers. Hirshfeld surface calculations supported by energy framework plots were also performed to better understand the relationship between the molecular structure and sensitivity. All the prepared (1,2,3-triazolyl)furazans show high nitrogen–oxygen contents (76–77%), good experimental densities (up to 1.72 g cm−3) and high positive enthalpies of formation (180–318 kJ mol−1) resulting in good detonation performances (D = 7.1–8.0 km s−1; P = 21–29 GPa). Overall, this work unveils novel strategies for the construction of balanced energetic melt-castable substances or plasticizers for various applications.

Epishina M. , Kulikov A. , Ananyev I.V. , Anisimov A.A. , Monogarov K.A. , Fershtat L.
Impact of regiochemistry in energetic materials science: a case of (nitratomethyl-1,2,3-triazolyl)furazans
Dalton Transactions. 2023. V.52. N22. P.7673-7683. DOI: 10.1039/d3dt00917c WOS Scopus OpenAlex

Web of science:	WOS:000989144300001
Scopus:	2-s2.0-85160403806
OpenAlex:	W4375927500

DB	Citing
OpenAlex	23
Scopus	23
Web of science	23