Portius, P. orcid.org/0000-0001-8133-8860, Adams, M., Cross, M. et al. (1 more author) (2023) Synthesis, structure and reactivity of energetic nitrobis(pyrazolyl)benzenes. In: Akhavan, J., (ed.) Future Developments in Explosives and Energetics: 1st International Explosives Conference. 1st International Explosives Conference (IEC-2022), 22-24 Jun 2022, London, United Kingdom. Royal Society of Chemistry , pp. 17-45. ISBN 9781788017855
Abstract
Two new energetic nitroaromatic compounds, 1,4-bis(1H-pyrazol-4'-yl)-2,5-dinitrobenzene (H2dpzb(NO2)2) and 1,4-bis(1H-3',5'-dinitropyrazol-4'-yl)-2,5-dinitrobenzene (H2dpzb(NO2)6), were prepared by nitration of 1,4-bis(1H-pyrazol-4'-yl)benzene (H2dpzb) with mixed acid. H2dpzb(NO2)x were isolated as yellow powders in moderate yields. They are stable under ambient conditions, soluble in dimethylformamide and dimethylsulfoxide, but poorly soluble in weakly coordinating solvents, and deflagrate in the heat. Both compounds have been characterised by 1H, 13C NMR and IR spectroscopies as well as by X-ray crystallography. H2dpzb(NO2)x crystallise readily as impact-insensitive dmso or thf solvates. Due to steric crowding at the (pyrazolyl group)–(benzene) bonds, H2dpzb(NO2)x adopt a twisted molecular geometry with extended (x = 2) or localised intermolecular hydrogen-bonding (x = 6) that involve the pyrazolyl H atoms and solvent of crystallisation. H2dpzb(NO2)6 reacts with base to form crystalline [B-H]2[dpzb(NO2)6], B = NEt3, which possesses remarkably high density ([B-H]2[dpzb(NO2)6]), or a powder consisting of Na2dpzb(NO2)6 (B = NaHCO3, crystallised as the coordination polymer Na(dmso)(dpzb(NO2)6). A mixture of H2dpzb(NO2)6, Zn(NO3)2, NEt3, dmso and water afforded the coordination compound [Zn(κ(O)-dmso)6]2[dpzb(NO2)6].
Metadata
Item Type: | Proceedings Paper |
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Authors/Creators: |
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Editors: |
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Copyright, Publisher and Additional Information: | © 2023 Royal Society of Chemistry |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 03 May 2023 16:23 |
Last Modified: | 15 Sep 2023 15:49 |
Status: | Published |
Publisher: | Royal Society of Chemistry |
Refereed: | Yes |
Identification Number: | 10.1039/9781839162350-00015 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:198739 |