High-density insensitive energetic materials: 2,4,6-tris(2-fluoro-2,2-dinitroethoxy)-1,3,5-triazine

Гидаспов, А. А.; Бахарев, В. В.; Suponitsky, Kyrill Yu.; Nikitin, V. G.; Sheremetev, Aleksei B.

doi:10.1039/c6ra24629j

Cited by 30 publications

(10 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Such a qualitative analysis can be supplemented by an estimation of the energy between the central molecule and each molecule from its closest environment (pair interaction energy). The latter can be done in terms of atom-atom potentials, quantum chemical calculations of dimers (molecular pairs) at different levels of theory, semi-empirical methods based on electron density distribution, such as PIXEL or CE-B3LYP, "Atoms in molecules" (AIM) topological theory [43][44][45][46][47][48][49]. All those methods can be successfully used for crystals built up of neutral molecules.…”

Section: Methodology Of Crystal Structure Investigationmentioning

confidence: 99%

Energetic Co-Crystal of a Primary Metal-Free Explosive with BTF. Ideal Pair for Co-Crystallization

et al. 2021

Self Cite

View full text Add to dashboard Cite

Co-crystallization is an elegant technique to tune the physical properties of crystalline solids. In the field of energetic materials, co-crystallization is currently playing an important role in the engineering of crystals with improved performance. Here, based on an analysis of the structural features of the green primary explosive, tetramethylammonium salt of 7-oxo-5-(trinitromethyl)-4,5,6,7-tetrahydrotetrazolo[1,5-a][1,3,5]triazin-5-ide (1), a co-former such as the powerful secondary explosive, benzotrifuroxan (BTF, 2), has been proposed to improve it. Compared to the original 1, its co-crystal with BTF has a higher detonation pressure and velocity, as well as an initiating ability, while the impact sensitivity and thermal stability remained at about the same level. Both co-formers, 1 and 2, and co-crystal 3 were characterized by single-crystal X-ray diffraction and their crystal packing was analyzed in detail by the set of approaches, including periodic calculations. In the co-crystal 3, all intermolecular interactions were significantly redistributed. However, no new types of intermolecular interactions were formed during co-crystallization. Moreover, the interaction energies of structural units in crystals before and after co-crystallization were approximately the same. A similar trend was observed for the volumes occupied by structural units and their densifications. The similar nature of the organization of the crystals of the co-formers and the co-crystal gives grounds to assert that the selected co-formers are an ideal pair for co-crystallization, and the invariability of the organization of the crystals was probably responsible for the preservation of some of their properties.

show abstract

Section: Methodology Of Crystal Structure Investigationmentioning

confidence: 99%

Energetic Co-Crystal of a Primary Metal-Free Explosive with BTF. Ideal Pair for Co-Crystallization

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…Water H atom positions were refined and OÀ H distances were restrained to 0.84(2) Å. U iso (H) values were set to a multiple of U eq (C) with 1.5 for CH 3 and OH, and 1.2 for CH 2 , and NH 2 units, respectively. The structures of ( 3) to ( 6) are all solvates with one molecule of water ( 3), one molecule of acetone ( 4), two molecules of methanol (5) or one molecule of methoxy ethanol ( 6) per formula unit of ANTT. Additional data collection and refinement details, including description of disorder (where present) can be found in the sections below and Table 1.…”

Section: Crystal Structuresmentioning

confidence: 99%

Synthesis and characterization of the energetic 5,7‐diamino‐2‐nitro‐1,2,4‐triazolo[1,5‐a]‐1,3,5‐triazine

Roux,

Zeller,

Byrd

et al. 2023

Propellants Explo Pyrotec

View full text Add to dashboard Cite

The energetic compound 5,7‐diamino‐2‐nitro‐1,2,4‐triazolo[1,5‐a]‐1,3,5‐triazine (ANTT) was synthesized through the selective nitration of 2,5,7‐triamine‐1,2,4‐triazolo[1,5‐a]‐1,3,5‐triazine (TTT). This facile synthetic strategy yields a highly insensitive energetic nitrogen bicycle with potential for further functionalization. ANTT was chemically characterized by NMR, IR, and single crystal X‐Ray crystallography. Its energetic sensitivities (impact, friction) were experimentally determined, and its energetic performances were calculated for the first time.

show abstract

“…One of them is based on a combination of the geometric 40 and energy 41-44 approaches and is widely employed for the crystal packing analysis. [45][46][47][48][49] This method includes the analysis of a system of shortened contacts (shorter than the sum of the van der Waals radii 50 ) combined with the evaluation of the energy of interactions between the central molecule and the molecules in its nearest environment in the crystal. The molecule is included in the nearest environment if at least one interatomic contact is shorter than the sum of the van der Waals radii plus 0.5 Å.…”

Section: Experimental and Calculationsmentioning

confidence: 99%

Crystal structure features of nitro derivatives of methylcytizine and their relationship with second-order nonlinear optical susceptibility

et al. 2020

View full text Add to dashboard Cite

The crystal packings of mono-(1) and dinitro derivatives (3) of methylcytizine are analyzed in terms of combined geometric and energy approaches and based on the evaluation of the degree of molecular deformation (a decrease in the molecular volume) in going from the free molecule to the crystal. An increase in the crystal density in going from the mono-to dinitro derivative (1.440 g cm-3 for 1 and 1.528 g cm-3 for 3 at 120 K) is associated with an increase in the density of the isolated molecule rather than with an increase in the packing density, which is almost equal in the crystals of compounds 1 and 3. The second-order nonlinear optical susceptibility of crystals was estimated in terms of a charge model, the prediction error of which is within 10%, being comparable with experimental accuracy. The similarity of the packing densities of compounds 1 and 3 enabled a detailed comparative analysis of the eff ect of the crystal fi eld on the nonlinear optical properties. Both compounds are characterized by relatively high nonlinear optical susceptibility, which is higher than that of urea, a commonly accepted standard, by a factor of 10 and 6.5 for compounds 1 and 3, respectively.

show abstract

High-density insensitive energetic materials: 2,4,6-tris(2-fluoro-2,2-dinitroethoxy)-1,3,5-triazine

Abstract: A Na3PO4-promoted nucleophilic substitution of all chlorine atoms of cyanuric with fluorodinitroethanol was achieved with excellent yield. The product demonstrates promising potential for diverse applications like explosives or propellants.

Cited by 30 publications

References 29 publications

Energetic Co-Crystal of a Primary Metal-Free Explosive with BTF. Ideal Pair for Co-Crystallization

Energetic Co-Crystal of a Primary Metal-Free Explosive with BTF. Ideal Pair for Co-Crystallization

Synthesis and characterization of the energetic 5,7‐diamino‐2‐nitro‐1,2,4‐triazolo[1,5‐a]‐1,3,5‐triazine

Crystal structure features of nitro derivatives of methylcytizine and their relationship with second-order nonlinear optical susceptibility

Contact Info

Product

Resources

About