Synthesis, Structure and Energetic Properties of a Catenated  N6, Polynitro Compound: 1,1'-Azobis(3,5-Dinitropyrazole)

Li, Yanan; Shu, Yuanjie; Wang, Yinglei; Wang, Bozhou; Zhang, Shengyong; Bi, Fuqiang

doi:10.22211/cejem/70373

Cited by 5 publications

(4 citation statements)

References 32 publications

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“…In some cases, the desired compounds are found in the environment as minerals. Among the CEMs reported in the literature, the most frequent mentions are made of compounds in which the role of the central atom is fulfilled by cations such as Cr 3+ , Mn 2+ , Fe 3+ , Co 2+ , Ni 2+ , Cu 2+ and Zn 2+ [16][17][18]. Period 4 metal compounds are characterized by high spatial packing.…”

Section: Transition Metal Compoundsmentioning

confidence: 99%

“…The coordination number of the abovementioned cations is 6, except for the copper cation, whose coordination number is 4. Site coordination in the case of multidentate ligands provides the possibility of coordinating larger numbers of ligand molecules relative to metal salt molecules; the structures of these compounds are mostly octahedral and, except for mercury and copper, are characterized by a flat-coordinated geometry [16]. Compounds based on some of these elements, such as copper and cobalt, are not necessarily completely "green" as some forms of those elements show toxicity, but despite this, they are far more desirable than compounds based on lead.…”

Section: Transition Metal Compoundsmentioning

confidence: 99%

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Coordination Energetic Materials—Scientific Curiosity or Future of Energetic Material Applications?

2022

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Significant incentives for developing and introducing new energetic materials to the industrial-scale production and application of new energetic materials have stimulated extensive research on the subject. Despite numerous studies, which have reported a broad array of results, progress in this field remains limited as the research results do not translate into commensurate practical applications. Coordination energetic materials are one of the promising classes of such materials. Despite more than two decades of research efforts dedicated to these substances and their advantages over classical energetic materials, in terms of performance parameters and safety parameters, these materials have not found any broader practical application. In this work, selected representative literature reports dedicated to these materials have been analysed in order to present the possible reasons for this state. Some suggestions about the future direction of research and development efforts dedicated to coordination energetic materials have also been formulated. The publication is one voice in the discussion on new challenges related to the search for new lead-free explosives.

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Section: Transition Metal Compoundsmentioning

confidence: 99%

Section: Transition Metal Compoundsmentioning

confidence: 99%

Coordination Energetic Materials—Scientific Curiosity or Future of Energetic Material Applications?

2022

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“…Moreover, these molecules usually have better performance than parent non-linked heterocycles since they contain the azo explosophore moiety [7]. Amongst the most important energetic azo compounds, there are derivatives of 1,2,3,4-tetrazine ( Figure 1, 1a), tetrazole (1b), 1,2,4-triazole (1c), and pyrazole (1d) [8][9][10][11]. Nitrated imidazoles are of great interest due to their low sensitivity towards various stimuli and high detonation parameters, but Nevertheless, several derivatives with aliphatic or aromatic substituents have been reported and they may serve as photoswitches and dyes [16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Structure and Thermal Properties of 2,2′-Azobis(1H-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds

et al. 2020

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A high-nitrogen compound, 2,2′-azobis(1H-imidazole-4,5-dicarbonitrile) (TCAD), was synthesized from commercially available 2-amino-1H-imidazole-4,5-dicarbonitrile. It was characterized with infrared and nuclear magnetic resonance spectroscopy. Its structure was determined by single crystal X-ray diffraction. The crystal of TCAD tetrahydrate is monoclinic, with space group P21/c with crystal parameters of a = 10.2935(2) Å, b = 7.36760(10) Å, c = 20.1447(4) Å, V = 1500.27(5) Å3, Z = 4, and F(000) = 688. Computational methods were used in order to fully optimize the molecular structure, calculate the electrostatic potential of an isolated molecule, and to compute thermodynamic parameters. TCAD has very high thermal stability with temperature of decomposition at 369 °C. Kinetics of thermal decomposition of this compound were studied and apparent energy of activation as well as the maximum safe temperature of technological process were determined.

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“…Recently, polynitroimidazoles have attracted considerable interest as energetic materials [3,4], especially highly energetic materials [5]. Many articles have reported new synthetic methods, explosive properties and applications of nitroimidazole derived compounds [6][7][8][9]. 2,4,5-Trinitroimidazole (Scheme 1, compound 2) is one nitroimidazole derivative, but it is not stable enough to be isolated [10].…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure and Thermal Behavior of Imidazolium 2,4,5-Trinitroimidazolate

Chen¹,

Lian²,

Chen³

et al. 2019

Cent. Eur. J. Energ. Mater.

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In this work, imidazolium 2,4,5-trinitroimidazolate was obtained from 2,4,5-tri-iodoimidazole in a yield of 48%. Single-crystal X-ray diffraction analysis showed that this compound belongs to the triclinic crystal system with space group P-1. Thermogravimetric-differential scanning calorimetry (TG-DSC) was performed under a nitrogen atmosphere at heating rates of 5, 10, 15 and 20 °C·min −1 . Compound 3 clearly exhibits an exothermic decomposition. The activation energy (E) and pre-exponential factor (lnA) calculated by the Kissinger method were 113.67 kJ·mol −1 and 25.30 s −1 , respectively. The E values obtained by the FWO and KAS methods changed slightly from 103.33 to 113.69 kJ·mol −1 and from 101.52 to 111.97 kJ·mol −1 , respectively, which makes us believe that its thermal decomposition can be described using only one reaction model. The Šatava-Šesták method and the compensation effect were used to study the thermal decomposition mechanism of imidazolium 2,4,5-trinitroimidazolate.is regarded as the most appropriate thermal decomposition kinetic equation. The impact sensitivity, friction sensitivity, detonation velocity and explosion pressure of imidazolium 2,4,5-trinitroimidazolate were 43 cm, 46%, 7056.9 m·s −1 and 1.9703 · 10 10 Pa (ρ = 1.538 g·cm −3 ), respectively. Imidazolium 2,4,5-trinitroimidazolate is incompatible with RDX, HMX, TKX-50 and CL-20.Supporting Information (SI), i.e. kinetic model functions, crystallographic data, spectra of FTIR and 1 H and 13 C NMR, and HPLC, for compound 3, as well as DSC curves of single and mixture systems, are available at:

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Synthesis, Structure and Energetic Properties of a Catenated N6, Polynitro Compound: 1,1'-Azobis(3,5-Dinitropyrazole)

Cited by 5 publications

References 32 publications

Coordination Energetic Materials—Scientific Curiosity or Future of Energetic Material Applications?

Coordination Energetic Materials—Scientific Curiosity or Future of Energetic Material Applications?

Structure and Thermal Properties of 2,2′-Azobis(1H-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds

Crystal Structure and Thermal Behavior of Imidazolium 2,4,5-Trinitroimidazolate

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