Crystal and molecular structure of hexanitrobenzene

Akopyan, Z. A.; Struchkov, Yu. T.; Dashevskii, V. G.

doi:10.1007/bf00744430

Cited by 29 publications

(24 citation statements)

References 5 publications

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“…Recently, Ma et al carefully investigated and compared the molecular structures of 20 traditional EMs composed of C, H, O, and N atoms. , According to the previously mentioned definition, TATB, DATB, NQ, DAAzF, DAAF, DNDP, NTO, TNA, α-FOX-7, LLM-105, and TNB belong to low-sensitivity or insensitive EMs; whereas ONDO, PETN, TNAZ, RDX, β-HMX, BCHMX, HNB, ONC, ε-CL-20, and BTF belong to sensitive ones. Among these 20 energetic molecules, only the sensitive BTF is hydrogen free.…”

Section: Planar π-Bonded Energetic Moleculesmentioning

confidence: 99%

π–π Stacking Contributing to the Low or Reduced Impact Sensitivity of Energetic Materials

Xiong

Zhang

2020

Crystal Growth & Design

105

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π−π stacking, usually together with the aid of hydrogen bonding (HB), serves as a main characteristic of low impact, sensitive, highly energetic materials (LSHEMs), which are highly desired for application, and attracts considerable attention in designing and synthesizing new EMs. This Perspective highlights the progress of the insights into the π−π stacking of EMs, covering traditional energetic crystals with homogeneous neutral molecules, energetic cocrystals (ECCs), and energetic ionic salts (EISs). A rather large π-bond is a requisite for the π−π stacking, and the π−π stacking can be classified into four patterns, including face-to-face stacking, wavelike stacking, crossing stacking, and mixing stacking, with an increasing difficulty in shear sliding, and HB plays an important role in supporting sliding layers. Straightforwardly, the stacking pattern−impact sensitivity relationship is rooted in the steric hindrance when sliding, and the face-to-face π−π stacking is preferred to design LSHEMs at the crystal level, due to the least steric hindrance or the lowest sliding barrier among the four patterns. This stacking has been extensively observed in traditional EMs, ECCs, and EISs, enlightening us to make a rule for designing new EMs with such stacking. However, it is still difficult to make the rule, attributed to the unclear relationship between molecular and stacking structures. Maybe, it will become increasingly feasible to achieve the rule by establishing a database with detailed information on molecules and related stacking patterns, increasing the amount of data by collecting experimental and predicted results, and combining with advanced machine learning technologies. Combining this article with a recent review of HB in EMs (Cryst. Growth Des. 2019, 19 (10), 5981−5997), an overall perspective of intermolecular interactions in energetic crystals with C, H, O, and N atoms could have been presented.

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Section: Planar π-Bonded Energetic Moleculesmentioning

confidence: 99%

π–π Stacking Contributing to the Low or Reduced Impact Sensitivity of Energetic Materials

Xiong

Zhang

2020

Crystal Growth & Design

105

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“…Notably, most HEDMs have relatively low symmetry with the space group number (SGN) smaller than 62, with P2 1 /c (SGN = 14) being the most popular space group. Furthermore, the geometries of the 67 HEDMs were optimized based on the conjugate gradient method (Magnus and Stiefel, 1952), with the lattice parameters and atomic coordinates from single-crystal X-ray crystallography data as input (Crawford et al, 2007;Cai et al, 1983;Akopyan et al, 1966;Cady and Larson, 1965;Bagryanskaya and Gatilov, 1983;Meents et al, 2008;Wilkins and Small, 1982;Lind, 1970;Bracuti, 1996;Zhurova et al, 2006Zhurova et al, , 2007Nie et al, 2001;Bryden, 1972;Adam et al, 2002;Trotter, 1960;Oyumi and Brill, 1988;Graeber and Morosin, 1974;Altmann et al, 1998;Choi, 1981;Turley, 1968;Espenbetov et al, 1984;Archibald et al, 1990;Zhurova and Pinkerton, 2001;Li et al, 2005;Abrahams, 1950;Reeve and Miller, 2002;Sarma and Nagaraju, 2000;Dickinson et al, 1966;Hakey et al, 2008;Millar et al, 2009Millar et al, , 2010Cady et al, 1963Cady et al, , 1966Cobbledick and Small, 1974;;Ou et al, 1998;Bolotina et al, 2004;Thallapally et al, 2004;…”

Section: Crystalline Structures: Theoretical Optimization and Experimental Validationmentioning

confidence: 99%

Strategies for Achieving Balance between Detonation Performance and Crystal Stability of High-Energy-Density Materials

Zong

et al. 2020

iScience

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Performance-stability contradiction of high-energy-density materials (HEDMs) is a long-standing puzzle in the field of chemistry and material science. Bridging the gap that exists between detonation performance of new HEDMs and their stability remains a formidable challenge. Achieving optimal balance between the two contradictory factors is of a significant demand for deep-well oil and gas drilling, space exploration, and other civil and defense applications. Herein, supercomputers and latest quantitative computational strategies were employed and high-throughput quantum calculations were conducted for 67 reported HEDMs. Based on statistical analysis of large amounts of physico-chemical data, in-crystal interspecies interactions were identified to be the one that provokes the performancestability contradiction of HEDMs. To design new HEDMs with both good detonation performance and high stability, the proposed systematic and comprehensive strategies must be satisfied, which could promote the development of crystal engineering of HEDMs to an era of theory-guided rational design of materials. ''materials genome'' approach, based on the theoretical calculations of six-member aromatic and

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“…This can be explained by the electron pushing amine group, which pushes electrons into the bond, and as a consequence the bond length is shortened. Comparing the bond lengths with benzene derivatives with uniform groups, such as hexaaminobenzene and hexanitrobenzene, equal bond lengths of about 1.39 Å are observed [22][23]. The same effect is seen with the different CÀ N bond lengths.…”

Section: Single Crystal Structure Analysismentioning

confidence: 71%

Spectroscopic, Structural and Energetic Properties of Pentanitroaniline

Klapötke

Krumm

Riedelsheimer

2022

Propellants Explo Pyrotec

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Although pentanitroaniline (PNA) has been known for almost 100 years, as well as with an optimized synthesis, it is still not fully characterized. In this contribution, the crystal structure of PNA is reported for the first time without any adducts or solvents, allowing a view of the crystal packing, as well as the exact positioning of the nitro groups relative to each other. In addition, based on the crystal structure, a Hirshfeld analysis was performed, which determines the distances and types of interactions of the outer atoms. The compound was also studied in detail by NMR, especially with respect to 13C and 14N, making this a challenge due to sensitivity in solution. Furthermore, the compound was fully characterized by IR spectroscopy and TGA, as well as the sensitivities, were measured. Using the density obtained from X‐ray crystallography, as well as the heat of formation calculated with the gaussian program package, the energetic parameters were calculated using explo5 computer code. The performance data were compared to the commonly used RDX and oxidizer ammonium perchlorate, as well as the structurally similar triaminotrinitro (TATB) and pentanitro (PNB) benzene.

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Crystal and molecular structure of hexanitrobenzene

Cited by 29 publications

References 5 publications

π–π Stacking Contributing to the Low or Reduced Impact Sensitivity of Energetic Materials

π–π Stacking Contributing to the Low or Reduced Impact Sensitivity of Energetic Materials

Strategies for Achieving Balance between Detonation Performance and Crystal Stability of High-Energy-Density Materials

Spectroscopic, Structural and Energetic Properties of Pentanitroaniline

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