Pyrazine 1,4-Dioxide is a Prolific Cocrystal Former and Energetic Material Itself

Pyrazine 1,4-Dioxide is a Prolific Cocrystal Former and Energetic Material Itself Full article

Journal

Crystal Growth & Design
ISSN: 1528-7483 , E-ISSN: 1528-7505

Output data

Year: 2024, Volume: 24, Number: 2, Pages: 741-746 Pages count : 6 DOI: 10.1021/acs.cgd.3c01146

Authors

Monogarov Konstantin A. ¹ , Melnikov Igor N. ¹ , Vatsadze Irina A. ² , Dalinger Igor L. ² , Ananyev Ivan V. ³ , Muravyev Nikita V. ¹

Affiliations

1	Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, 4 Kosygina Str., 119991 Moscow, Russia
2	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky Prospect 47 Moscow, Russia
3	Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, GSP-1, Leninsky Prospect, 31, 119991 Moscow, Russia

Pyrazine 1,4-dioxide (PZDO) is a chemical frequently employed as a coformer in cocrystal design. It has two N-oxide fragments that signify potential hazards, but we found no information about it in prior literature. Therefore, we investigate the thermal behavior, thermochemical properties, and mechanical sensitivity of the title compound. We demonstrate that the material explodes in standard impact tests at a certain drop energy. By the level of its computed energetic potential, PZDO approaches benchmark trinitrotoluene. We screened ten energetic materials for cocrystal formation with PZDO using thermal analysis methods and predicted three novel cocrystals. However, we failed to grow the X-ray quality crystals by the conventional approach due to significantly differing solubility of PZDO and other components in common solvents. Two suitable coarse cocrystals of 3,4-dinitropyrazole/PZDO and 3,5-dinitropyrazole/PZDO were finally prepared by resublimation (vacuum recondensation of preformed comelt), and its X-ray structure is reported. Overall, we characterize PZDO as an energetic material and highlight the potential risks associated with the compound. The preparation of cocrystals via the gas phase route, although laborious, may be effective when the traditional (via solution) approach fails.

Monogarov K.A. , Melnikov I.N. , Vatsadze I.A. , Dalinger I.L. , Ananyev I.V. , Muravyev N.V.
Pyrazine 1,4-Dioxide is a Prolific Cocrystal Former and Energetic Material Itself
Crystal Growth & Design. 2024. V.24. N2. P.741-746. DOI: 10.1021/acs.cgd.3c01146 WOS Scopus OpenAlex

Web of science:	WOS:001144581900001
Scopus:	2-s2.0-85181572248
OpenAlex:	W4390502300

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OpenAlex	3
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