The energetic 3-trinitromethyl-5-nitramino-1H-1,2,4-triazole and nitrogen-rich salts

Hermann, T. S.; Klapötke, Thomas M.; Krumm, Burkhard; Stierstorfer, Jörg

doi:10.1039/c7nj00695k

Cited by 21 publications

(10 citation statements)

References 20 publications

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“…APPENDIX A References to experimental data used in this work Sorted alphabetically by CSD refcodes: ACUCIN (Nikonova et al, 2018), ADOWUO (Hermann et al, 2017), AHUKIZ (Weber et al, 2015), AMEPOS (Janicki & Starynowicz, 2010), ARAQUH (Hemgesberg et al, 2016), BECFAT (Veronelli et al, 2017), CAMVES (Dittrich et al, 2002), DAYCEO (Uppal et al, 2017), DNEDAM01 (Gruhne et al, 2021), DUBWAB (Nugrahani et al, 2019), DUCMAQ (Grabowsky et al, 2009), EDAWIP (Evans & Gilardi, 2001), EGUFIY (Malassis et al, 2019), GLYALB08 (Capelli et al, 2014), IYAQOP02 (Marshall et al, 2016), KOVPIX (Thanzeel et al, 2019), LETHIE (Chen et al, 2018), LOKPOT (Ballmann et al, 2019), LOSLEL (Johnas et al, 2009), MANMUJ08 (Jorgensen et al, 2014), MOSCOP (Clegg, 2019), MOVPIZ (Lapointe et al, 2019), MUHBOI (Butschke et al, 2015), OXACDH46 (Kamin ´ski et al, 2014), PCYPOL04 (Mohanraj et al, 2018), PPHCHN11…”

Section: Discussionmentioning

confidence: 99%

Fragmentation and transferability in Hirshfeld atom refinement

Chodkiewicz¹,

Pawlędzio²,

Woińska³

et al. 2022

IUCrJ

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Hirshfeld atom refinement (HAR) is one of the most effective methods for obtaining accurate structural parameters for hydrogen atoms from X-ray diffraction data. Unfortunately, it is also relatively computationally expensive, especially for larger molecules due to wavefunction calculations. Here, a fragmentation approach has been tested as a remedy for this problem. It gives an order of magnitude improvement in computation time for larger organic systems and is a few times faster for metal–organic systems at the cost of only minor differences in the calculated structural parameters when compared with the original HAR calculations. Fragmentation was also applied to polymeric and disordered systems where it provides a natural solution to problems that arise when HAR is applied. The concept of fragmentation is closely related to the transferable aspherical atom model (TAAM) and allows insight into possible ways to improve TAAM. Hybrid approaches combining fragmentation with the transfer of atomic densities between chemically similar atoms have been tested. An efficient handling of intermolecular interactions was also introduced for calculations involving fragmentation. When applied in fragHAR (a fragmentation approach for polypeptides) as a replacement for the original approach, it allowed for more efficient calculations. All of the calculations were performed with a locally modified version of Olex2 combined with a development version of discamb2tsc and ORCA. Care was taken to efficiently use the power of multicore processors by simple implementation of load-balancing, which was found to be very important for lowering computational time.

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Section: Discussionmentioning

confidence: 99%

Fragmentation and transferability in Hirshfeld atom refinement

Chodkiewicz¹,

Pawlędzio²,

Woińska³

et al. 2022

IUCrJ

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“… Previously, we have reported the synthesis of C-trinitromethyl-substituted pyrazoles by the reaction of N 2 O 4 with pyrazolecarbaldehyde oxime . Among them, 1-nitro-3-trinitromethylpyrazole exhibits not only the highest density and detonation performance but also a poor thermal stability and the highest sensitivity to impact and friction, which is the result of the combined effect of trinitromethyl and nitramine groups. , Given the established instability of trinitromethyl group at high temperature, the dinitromethyl with a coplanar geometric structure is expected to give rise to a better stability as well as a lower sensitivity . Interestingly, the denitration reactions of trinitromethyl groups attached to imidazoles, triazoles, and tetrazoles into the corresponding dinitromethylide salts by the treatment with hydrazine and hydroxylamine have been reported. − Based on these successful examples, 1-nitro-3-trinitromethylpyrazole was subject to attempted analogical conversion.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Energetic Hydrazinium 5-Nitro-3-dinitromethyl-2H-pyrazole by Unexpected Isomerization of N-Nitropyrazole

Zhang

et al. 2019

ACS Omega

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A new energetic salt, hydrazinium 5-nitro-3-dinitromethyl-2H-pyrazole, was synthesized using 1-nitro-3-trinitromethylpyrazole and hydrazine as raw materials and fully characterized by IR and NMR spectroscopy, elemental analysis, and X-ray crystallography. The isomerization of N-nitropyrazole in the reaction condition was first reported and the possible mechanism was explained by the density functional theory method. The salt has good density, high positive enthalpy of formation superior to those of the RDX and HMX, and good detonation properties comparable to those of RDX. By denitration and isomerization reactions, the salt gains a better thermal stability and lower sensitivity toward impact and friction compared with its parent compound. Based on an overall energetic evaluation, the salt has a promising future as an alternative explosive. The research also contributes to the synthesis and application of polynitro-substituted N-heterocyclic compounds as energetic materials.

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“…The traditional sources of energetic materials are five‐membered or six‐membered nitrogen‐containing heterocycles. Especially, triazole, tetrazole, and tetrazine derivatives have always been designed and synthesized as the energetic compounds theoretically and experimentally …”

Section: Introductionmentioning

confidence: 99%

Molecular design of a new family of bridged bis(multinitro‐triazole) with outstanding oxygen balance as high‐density energy compounds

Zhang

2019

Int J of Quantum Chemistry

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A new family of bridged bis(multinitro-triazole) was designed and investigated using the density functional theory method. The density, oxygen balance, heat of formation, detonation performance, and impact sensitivity were calculated systematically. The results show that the multinitromethyl groups play an important role in increasing densities. At the same time, different bridged groups present diverse performances with high density (1.86-1.96 gÁcm −3 ), excellent detonation properties (V = 8.72 kmÁs −1 -9.20 kmÁs −1 ; P = 34.54 GPa-39.49 GPa), outstanding oxygen balance (0%-11.59%), and acceptably impact sensitivity. Especially, tetrazine (M7)-bridged and diaminofurazan (M9)-bridged groups are very helpful for enhancing their detonation performance (V (M7) = 9.12 kmÁs −1 , P (M7) = 38.51 GPa; V (M9) = 9.20 kmÁs −1 , P (M9) = 39.49 GPa), respectively, which are better than RDX. They could be seen as the potential candidates of high energy density materials (HEDMs). K E Y W O R D Sbridged bis(multinitro-triazole), detonation properties, oxygen balance, DFT | INTRODUCTIONRecently, symmetric compounds with bridging have been found. They are regarded as the most promising strategies in the design of highperformance energetic compounds [1][2][3] with the merits of high density, high positive heat of formation, good detonation performances, and excellent thermal stability. [4][5][6][7][8][9][10] The energetic materials of nitrogen-rich organic compounds increasingly become attracting as the promising candidates in the challenging field of energetic materials research. The traditional sources of energetic materials are five-membered or six-membered nitrogen-containing heterocycles. Especially, triazole, tetrazole, and tetrazine derivatives have always been designed and synthesized as the energetic compounds theoretically and experimentally. [11][12][13] The energetic compounds with bridged groups such as 5,5 0 -dinitro-3,3 0 -azo-1,2,4-triazole [14] or the analog nitrimino compound [15] have shown remarkably high decomposition temperatures and excellent energetic properties. Nowadays, many researchers have investigated the combination of the heterocycles with bistetrazoles [16,17] and bistriazoles [18,19] As components of composite high-energy materials with high density and positive oxygen balance, polynitrogenated compounds are of interest for researchers. [20] Of course, the trinitro group is always deemed as the unit, which can increase density dramatically and improve oxygen balance, thereby enhancing detonation performance. Shreeve and coworkers [21] reported the synthesis of various polynitro-1,2,4 triazoles, which contain trinitromethyl groups and display potentially significant physical and energetic properties. Klapötke [22] team focused the contribution of bis-1,2,4-triazoles carrying nitro, dinitromethyl energetic groups. Semenov [20] presented the 2,2 0 -bis(trinitromethyl)-derivatives formed the N,N 0 -Dinitromethyl derivatives of 5,5 0dinitrobi(1,2,4-triazole) by a sequence of nitration, fluorination, an...

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The energetic 3-trinitromethyl-5-nitramino-1H-1,2,4-triazole and nitrogen-rich salts

Abstract: An oxygen- and nitrogen-rich energetic triazole as an excellent example with outstanding performance but high sensitivity, which can be adjusted by the formation of nitrogen-rich salts.

Cited by 21 publications

References 20 publications

Fragmentation and transferability in Hirshfeld atom refinement

Fragmentation and transferability in Hirshfeld atom refinement

Synthesis and Properties of Energetic Hydrazinium 5-Nitro-3-dinitromethyl-2H-pyrazole by Unexpected Isomerization of N-Nitropyrazole

Molecular design of a new family of bridged bis(multinitro‐triazole) with outstanding oxygen balance as high‐density energy compounds

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