Insight into structural and energetic features of substituted triazolofurazans

Insight into structural and energetic features of substituted triazolofurazans Научная публикация

Журнал

CrystEngComm
ISSN: 1466-8033

Вых. Данные

Год: 2024, Том: 26, Номер: 25, Страницы: 3349-3362 Страниц : 14 DOI: 10.1039/d4ce00329b

Авторы

Balabanova Sofya P. ¹ , Voronin Alexey A. ¹ , Churakov Alexandr M. ¹ , Klenov Michael S. ¹ , Fedyanin Ivan V. ^2,3 , Pivkina Alla N. ⁴ , Meerov Dmitry B. ⁴ , Kon'kova Tatiana S. ⁴ , Matyushin Yurii N. ⁴ , Strelenko Yurii A. ¹ , Erokhin Kirill S. ¹ , Zelenov Victor P. ¹ , Tartakovsky Vladimir A. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, Moscow, 119991, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St, Moscow, 119991, Russian Federation
3	HSE University, 101000 Moscow, Russian Federation
4	N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Building 1, 119991, Moscow, Russian Federation

A comparative study of experimentally established structures, stability and energetic performance of ammonium and hydrazinium salts of 4H-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole (triazolofurazan, TF) as well as its N-oxide and N-nitroimide was performed. The aim of this study was to reveal the structure–property relationships of heterocyclic systems by the example of triazolofurazan derivatives. It was shown that the introduction of N-oxide oxygen into position 5 of the TF anion led to a small loss in enthalpy of formation (4 kcal mol−1) while the introduction of the N–NO2 (N-nitroimido) group in the same position added a significant amount of energy into the molecule (36 kcal mol−1). Both substituents improved the oxygen balance and increased the density (0.065–0.22 g cm−3) of the final salts; however, only N-oxide enhanced the thermal stability by ca. 35–45 °C, while N-nitroimide either remained unchanged or decreased the heat resistance compared to unsubstituted analogues.

Balabanova S.P. , Voronin A.A. , Churakov A.M. , Klenov M.S. , Fedyanin I.V. , Pivkina A.N. , Meerov D.B. , Kon'kova T.S. , Matyushin Y.N. , Strelenko Y.A. , Erokhin K.S. , Zelenov V.P. , Tartakovsky V.A.
Insight into structural and energetic features of substituted triazolofurazans
CrystEngComm. 2024. V.26. N25. P.3349-3362. DOI: 10.1039/d4ce00329b WOS Scopus OpenAlex

≡ Web of science:	WOS:001237947200001
≡ Scopus:	2-s2.0-85195375799
≡ OpenAlex:	W4396909238