Small Cation‐Based High‐Performance Energetic Nitraminofurazanates

Tang, Yongxing; He, Chunlin; Mitchell, Lauren A.; Parrish, Damon A.; Shreeve, Jean’ne M.

doi:10.1002/chem.201602171

Cited by 34 publications

(7 citation statements)

References 29 publications

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“…By incorporating energy-rich functional groups (-NO 2 , -NHNO 2 , -ONO 2 , etc.) into furazan backbones, a large number of energetic materials with excellent detonation properties were successfully developed (Tang et al, 2016;Liu et al, 2018;Zhai et al, 2019;Zhang et al, 2019). Meanwhile, it is noteworthy that an inevitable and inherent contradiction existed SCHEME 1 | (A-C) Electrostatic potential of compounds 6 and 8 [B3LYP/6-31+G** 0.001 electron/b3 isosurface, energy values −0.03 to +0.03 H].…”

Section: Introductionmentioning

confidence: 99%

A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance

Xue¹,

Bi²,

Zhang³

et al. 2020

Front. Chem.

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Design and synthesis of new compounds with both high detonation performances and good safety properties have always been a formidable task in the field of energetic materials. By introducing -ONO 2 and -NHNO 2 moieties into 1,2,4-oxadiazole-and 1,2,5-oxadiazole-based backbones, a new family of energetic materials, including ammonium 3-nitramino-4-(5-hydroxymethyl-1,2,4-oxadiazol-3-yl)-furazan (4), 3,3 ′ -bis[5-nitroxymethyl-1,2,4-oxadiazol-3-yl]-4,4 ′azofuroxan (6), [3-(4-nitroamino-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5-yl]-methylene nitrate (8), and its energetic ionic salts (10-12), were synthesized and fully characterized. The energetic and physical properties of the materials were investigated through theoretical calculations and experimental determination. The results show that the oxadiazole-based compounds exhibit high enthalpy of formations, good detonation performances, and extraordinary insensitivities. In particular, the hydrazinium salt (11) shows the best energetic properties (11: d =1.821 g cm −3 ; P = 35.1 GPa, v D = 8,822 m s −1 , IS = 40 J, FS > 360 N). The ESP and Hirshfeld surface analysis indicated that a large number of hydrogen bonds as well as π-π stacking interactions within molecules might be the key reason for their low sensitivities and high energy-density levels.

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Section: Introductionmentioning

confidence: 99%

A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance

Xue¹,

Bi²,

Zhang³

et al. 2020

Front. Chem.

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“…This result well matches to the previous report in which the combination of a large anion and small cation could form high-density energetic compounds. 37 Unlike most of the cations from ammonium to imidazolium ions, which were generally well distributed along the correlation line (dashed), the Dv values for hydrazinium groups (navy triangle) deviated from the correlation line (Fig. 4c).…”

Section: Structural Analysismentioning

confidence: 92%

“…It has been reported that hydrazinium ions pertain lower electrostatic potential (ESP), which is a critical clue in intermolecular interactions. 37 In particular, the deviation was larger when two hydrazinium ions were combined in an anion (cpd 307). Nonetheless, the hydrazinium group showed a higher Dv than guanidinium ions (Dv < 9,200 m/s).…”

Section: Structural Analysismentioning

confidence: 99%

Effect of ionic composition on thermal properties of energetic ionic liquids

et al. 2018

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A model to predict the effect of ionic composition on the thermal properties of energetic ionic liquids was developed by quantitative structure-property relationship modeling, which predicted the detonation velocity, pressure, and melting temperature of energetic ionic liquids. A hybrid approach was used to determine the optimal subset of descriptors by combining regression with the genetic algorithm as an optimization method. The model showed the high accuracy, reaching a correlation factor of R 2 as 0.71, 0.73 and 0.68 for the correlation between the calculated detonation velocity, pressure and melting temperature against reported values. It was validated extensively and compared to the Kamlet-Jacobs equation. The effect of ion composition on the thermal properties of energetic ionic liquids could be quantitatively analyzed through the developed model, to give an insight for the design of new energetic ionic liquids.

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“…More importantly, the combination of azoles with various energetic groups like amino, nitro, nitramino, azido, and polynitromethyl could produce a considerable variety of energetic materials, which have diverse properties and meet different demands of application. Compared with single heterocyclic structures, C–C bonded bisheterocyclic, ,− triheterocyclic, − and even tetraheterocyclic compounds usually have a higher heat of formation, good sensitivity, and better thermal stability derived from larger π-conjugated systems. Typical examples for these kinds of compounds are illustrated in Figure .…”

Section: Introductionmentioning

confidence: 99%

3,4-Bis(3-tetrazolylfuroxan-4-yl)furoxan: A Linear C–C Bonded Pentaheterocyclic Energetic Material with High Heat of Formation and Superior Performance

Zhai

Bi²,

Zhang³

et al. 2020

ACS Omega

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The design and preparation of new nitrogen-rich heterocyclic compounds are of considerable significance for the development of high-performing energetic materials. By combining nitrogen-rich tetrazole and oxygen-rich furoxan, a linear C–C bonded pentaheterocyclic energetic compound, 3,4-bis(3-tetrazolylfuroxan-4-yl) furoxan (BTTFO), was synthesized using a facile and straightforward method. Comprehensive X-ray analysis reveals the key role of hydrogen bonds, π–π interactions, and short contacts in the formation of dense packing of BTTFO and explains why a long chain-shaped molecule has a high density. This multicyclic structure incorporating three furoxan and two tetrazole moieties results in an exceptionally high heat of formation (1290.8 kJ mol–1) and favorable calculated detonation performances (v D, 8621 m s–1, P, 31.5 GPa). The interesting structure and fascinating properties demonstrated the feasibility of a linear multicyclic approach as a high-energy-density skeleton. Additionally, the thermodynamic parameters, electrostatic potential (ESP), and frontier molecular orbitals were also studied to get a better understanding of structure–property correlations.

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Small Cation‐Based High‐Performance Energetic Nitraminofurazanates

Cited by 34 publications

References 29 publications

A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance

A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance

Effect of ionic composition on thermal properties of energetic ionic liquids

3,4-Bis(3-tetrazolylfuroxan-4-yl)furoxan: A Linear C–C Bonded Pentaheterocyclic Energetic Material with High Heat of Formation and Superior Performance

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