5-(Dinitromethyl)-3-(trinitromethyl)-1,2,4-triazole and its derivatives: a new application of oxidative nitration towards <i>gem</i>-trinitro-based energetic materials

Dharavath, Srinivas; Zhang, Jiaheng; Imler, Gregory H.; Parrish, Damon A.; Shreeve, Jean’ne M.

doi:10.1039/c7ta00730b

Cited by 70 publications

(29 citation statements)

References 33 publications

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“…In general, not only the nitrogen atom of heterocycle possesses advantages of higher density and better thermal stability over their nonaromatic carbon-substituted analogues, but it also increases the heat of formation due to inherently energetic C–N and N–N bonds contained in the molecule. A variety of novel CHON energetic materials–based heterocycles have been reported as milestone achievements over the past several years, such as 4,4′-dinitro-3,3′-bisfuroxan 26 , 3-trinitromethyl-5-dinitromethyltrizole 27 , tetrazino-tetrazine 1,3,6,8-tetraoxide (TTTO) 28 – 30 , and 2,2′-dinitramino-5,5′-bi(1,3,4-oxadiazole) (ICM-101) 31 (Fig. 1 ).…”

Section: Introductionmentioning

confidence: 99%

New Strategy for Enhancing Energetic Properties by Regulating Trifuroxan Configuration: 3,4-Bis(3-nitrofuroxan-4-yl)furoxan

Zhai¹,

Bi²,

Luo³

et al. 2019

Sci Rep

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It is of current development to construct high–performance energetic compounds by aggregation of energetic groups with dense arrangement. In this study, a hydrogen-free high-density energetic 3,4-bis(3-nitrofuroxan-4-yl)furoxan (BNTFO-I) was designed and synthesized in a simple, and straightforward manner. Its isomer, 3,4-bis(4-nitrofuroxan-3-yl)furoxan (BNTFO-IV), was also obtained by isomerization. The structures of BNTFO-I and BNTFO-IV were confirmed by single-crystal X-ray analysis for the first time. Surprisingly, BNTFO-I has a remarkable calculated crystal density of 1983 g cm−3 at 296 K, which is distinctly higher than BNTFO-IV (1.936 g cm−3, 296 K), and ranks highest among azole-based CNO compounds yet reported. It is noteworthy that BNTFO-I exhibits excellent calculated detonation properties (vD, 9867 m s−1, P, 45.0 GPa). The interesting configuration differences of BNTFO-I and BNTFO-IV provide insight into the design of new advanced energetic materials.

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Section: Introductionmentioning

confidence: 99%

New Strategy for Enhancing Energetic Properties by Regulating Trifuroxan Configuration: 3,4-Bis(3-nitrofuroxan-4-yl)furoxan

Zhai¹,

Bi²,

Luo³

et al. 2019

Sci Rep

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“…The accurate values of total energies ( E 0 ), thermal corrections ( H T ), zero point energies (ZPE), molecular properties [17] and heats of formation (Δ H f ) of the designed compounds were calculated and summarized in Table S2. Generally speaking, energetic materials were always in the solid phase rather than gas phase and thus, values of Δ H f,solid were the main research subjects [18, 19]. From the table, it is seen that all the designed compounds possess positive Δ H f,solid ranges from 66.8 (A7) to 2302.0 kJ mol −1 (D2).…”

Section: Resultsmentioning

confidence: 99%

Investigation on a series of 3‐nitro‐1,2,4‐triazol‐5‐one based energetic derivatives: Molecular design and screening

Jin

Xiao

Liu

et al. 2020

Int J of Quantum Chemistry

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Density functional theory calculations at B3LYP/6‐311G(d,p) level were employed to investigate the relationships between the structures and properties of 3‐nitro‐1,2,4‐triazol‐5‐one based high energy density materials (HEDMs). The results show that all the designed compounds possess high positive heats of formation and the N3/NN substituents were found to be the effective structural units to improve the heats of formation. The calculated detonation velocities and detonation pressures indicate that substituting the XNO2/NN groups were very useful for enhancing the detonation properties of these designed compounds. In view of the bond dissociation energies of the weakest bonds, it reveals that most of the derivatives have acceptable thermal stabilities and the CN groups were beneficial to improve their thermal stabilities. Overall, the effects of the energetic groups on all the parameters combined with those of the different bridges. Compared to those of 1,3,5‐trinitro‐1,3,5‐triazinane and 1,3,5,7‐tetranitro‐1,3,5,7‐tetrazocane, four compounds (A7, B7, D7 and E7) were screened as possible HEDMs and their electronic structures were fully investigated to give better understanding of physicochemical properties and theoretical support for further experimental synthesis.

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“…8 Cations A and B ( Figure 1) were foreseen as significant precursors for energetic salts. [9][10][11][12][13][14][15][16] One of the driving forces for selecting these cations is their high nitrogen content that on decomposition produces large amounts of nitrogen gas and also helps to retain a good oxygen balance. Furthermore, the presence of amino groups in the cation can lead to a strong hydrogen bonding and will provide stability to structurally vibrant anions.…”

Section: Introductionmentioning

confidence: 99%

Computational assessment of energetic salts containing 7H-[1,2,4]triazolo[4,3-b][1,2,4]triazole

Nirwan

Ghule

2018

J Chem Sci

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The computational design of energetic salts based on 3,6,7-triamino-7H-[1,2,4]triazolo[4,3b][1,2,4]triazol-2-ium (cation A) and 3,7-diamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazol-2-ium (cation B) is described. Selective energetic anions have been combined with these cations to tune the performance parameters. All the designed salts (A1-11 and B1-11) exhibited reasonable densities ranging from 1.54 to 1.85 g/cm 3 , and positive heats of formation between 301 kJ/mol and 854 kJ/mol. The detonation properties for the A1-11 and B1-11 salts were computed using Kamlet-Jacobs method, and the corresponding values were found in the ranges of 6.12 km/s to 8.79 km/s and 15.12 GPa to 34.84 GPa. Admirable energetic performance and reasonable sensitivity indicate A4 and B4 as promising energetic salts.

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5-(Dinitromethyl)-3-(trinitromethyl)-1,2,4-triazole and its derivatives: a new application of oxidative nitration towards gem-trinitro-based energetic materials

Abstract: A family of 5-(dinitromethyl)-3-(trinitromethyl)-1,2,4-triazole and its derivatives was prepared using a new application of oxidative nitration with gem-trinitro-based energetics. These new compounds show promise for future energetic materials.

Cited by 70 publications

References 33 publications

New Strategy for Enhancing Energetic Properties by Regulating Trifuroxan Configuration: 3,4-Bis(3-nitrofuroxan-4-yl)furoxan

New Strategy for Enhancing Energetic Properties by Regulating Trifuroxan Configuration: 3,4-Bis(3-nitrofuroxan-4-yl)furoxan

Investigation on a series of 3‐nitro‐1,2,4‐triazol‐5‐one based energetic derivatives: Molecular design and screening

Computational assessment of energetic salts containing 7H-[1,2,4]triazolo[4,3-b][1,2,4]triazole

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