Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents DOI Creative Commons
Artyom E. Paromov

Molecules, Journal Year: 2023, Volume and Issue: 28(22), P. 7648 - 7648

Published: Nov. 17, 2023

The synthesis of substituted 2,4,6,8,10,12-hexaazaisowurtzitane via direct condensation is challenging. selection starting ammonia derivatives very limited. important step in developing alternative synthetic routes to these compounds investigate their formation process detail. Here, we examined an acid-catalyzed between benzyl carbamate and glyoxal a ratio 2:1 range polar protic aprotic solvents, discovered new occurring during the cascade with as well several processes hindering caged compounds. More specifically, cyclic compound, N,N′-bis(carbobenzoxy)-3,6-diamino-1,4-dioxane-2,5-diol, was found form at early stage under low acidity conditions. this compound governed by easier alcohol groups compared amide ones. intermediates, N,N′-bis(carbobenzoxy)ethan-1,2-diol, N,N′,N″-tris(carbobenzoxy)ethanol, N,N′,N″,N‴-tetrakis(carbobenzoxy)ethan, were obtained higher acidity. A solvents identified: those that react carbamate, promote progress side processes, precipitation intermediates. few byproducts isolated identified. It DMSO exhibits strong deactivating ability, while CH3CN activating ability towards glyoxal.

Language: Английский

Nitrogen-rich tetracyclic-based heterocyclic energetic materials DOI Creative Commons
Jie Tang, Hongwei Yang,

Guang-bin Cheng

et al.

Energetic Materials Frontiers, Journal Year: 2023, Volume and Issue: 4(2), P. 110 - 122

Published: May 18, 2023

This review provides numerous studies on nitrogen-rich tetracyclic-based heterocyclic energetic materials including oxadiazole, tetrazole, triazole, pyrazole, imidazole and tetrazine. The article mainly describes the construction method of skeleton, explosive modification, properties tetracyclic materials. structure-property relationship was obtained by comparing a series Finally, authors summarize synthesis laws skeletons, which reference for development in future.

Language: Английский

Citations

20
Expanding the Limits of Organic Energetic Materials: High-Performance Alliance of 1,3,4-Thiadiazole and Furazan Scaffolds DOI
Ilya Deltsov, Ivan V. Ananyev, Dmitry B. Meerov

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 174 - 182

Published: Dec. 11, 2023

A majority of known and newly synthesized energetic materials comprise polynitrogen or nitrogen–oxygen heterocycles with various explosophores. However, available structural combinations these organic scaffolds are finite about to reach their limits. Herein, we present the design synthesis a series sulfur-containing polyazole structures comprising 1,3,4-thiadiazole furazan rings linked by C–C bonds enriched nitro azo functionalities. In terms detonation performance, all 1,3,4-thiadiazole-furazan assemblies (D = 7.7–7.9 km s–1; P 26–28 GPa) lie between powerful explosive TATB 8.0 31 melt-cast material TNT 6.9 23 GPa). series, azo-bridged derivative 5 seems be most practically interesting, as it combines relatively high performance 7.9 28 GPa), very thermal stability (271 °C), insensitivity friction. By functional properties, outperforms benchmark heat-resistant hexanitrostilbene (HNS). To best our knowledge, this is first example an alliance rare case high-energy materials, which can certainly considered evolutionary step in science.

Language: Английский

Citations

20
Impact of Positional Isomerism on Melting Point and Stability in New Energetic Melt-Castable Materials DOI
Fang Chen, Yi Wang, Siwei Song

et al.

The Journal of Physical Chemistry C, Journal Year: 2023, Volume and Issue: 127(18), P. 8887 - 8893

Published: April 26, 2023

For an energetic material with a definite composition, the substituent position is most crucial factor to influence its physicochemical properties. Thus, it becoming increasingly important understand impact of positional isomerism on multidimensional properties differences. Herein, we reported two new potential melt-castable molecules, pair isomers (4-MMDNP and 5-MMDNP). These explosives exhibit obviously different properties, including densities (Δρ = 0.03 g cm–3), melting point (ΔTm 47.2 °C), decomposition temperature (ΔTd 27.3 stability (IS 20 J, FS 160 N vs IS 10 40 N), etc., even though they share similar compositions structures. Simultaneously, by analyzing crystal packing, intermolecular interactions, monomolecular parameters, were able uncover roots property Altogether, our results provide comprehensive molecular level insight into effect isomerism, which may be useful for design.

Language: Английский

Citations

16
Development of new nitrogen-oxygen systems in the Laboratory of Chemistry of Nitro Compounds at the Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences DOI
Michael S. Klenov, Aleksandr M. Churakov, Alexey A. Voronin

et al.

Russian Chemical Bulletin, Journal Year: 2024, Volume and Issue: 73(5), P. 1473 - 1494

Published: May 1, 2024

Language: Английский

Citations

5
Research progress on design, synthesis and performance of energetic polynitro hexaazaisowurtzitane derivatives: Towards improved CL-20 analogues DOI Creative Commons
Vladimir V. Parakhin, G. A. Smirnov

FirePhysChem, Journal Year: 2023, Volume and Issue: 4(1), P. 21 - 33

Published: May 25, 2023

In order to discover of high-energy materials with characteristics that surpass modern benchmarks, it is necessary study the widest range potential structures. The design energetic compounds using high-nitrogen cage scaffolds provides new opportunities. One promising representatives polycyclic multinitragen cages hexaazaisowurtzitane, since most powerful explosive CL-20 based on it. recent years, synthesis analogues has been actively developed. This review presents progress in synthesis, performance and structure-property relationship for polynitro hexaazaisowurtzitanes over past decade.

Language: Английский

Citations

11
New energetic 1,2,4‐triazole‐nitrofuroxan hybrids DOI
Alexander А. Larin,

Ekaterina V. Dubasova,

Ivan V. Ananyev

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(5), P. 713 - 722

Published: March 5, 2024

Abstract New promising energetic materials comprised of 1,2,4‐triazole and furoxan rings bearing explosophoric nitro group were rationally designed synthesized. All newly prepared compounds thoroughly characterized their physicochemical properties estimated. In the synthesized series, (1,2,4‐triazolyl)furoxan 4 is completely insensitive to impact friction possesses good detonation performance (D = 8.4 km s −1 ; P 33 GPa) enabling its further exploration as a high‐energy material.

Language: Английский

Citations

4
Understanding how Molecular Skeletal Isomerism Affects the Stability of Energetic Fused-ring Molecules: a Comparative Study of ICM-103 and NAPTO DOI Creative Commons

Ziwu Cai,

Tianyu Jiang, Wenquan Zhang

et al.

Energetic Materials Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

Citations

0
Covalently Bonded 1D Chains and 2D Networks From Si-Doped CL-20: Computational Study DOI
Margarita A. Gimaldinova, Mikhail M. Maslov, Savaş Kaya

et al.

Journal of Cluster Science, Journal Year: 2025, Volume and Issue: 36(3)

Published: April 4, 2025

Language: Английский

Citations

0
Development of novel HNIW/N2 host-guest explosives with enhanced stability and performance via pressure-temperature strategy DOI
Xiaomin Song,

Donghan Jia,

Shanhu Sun

et al.

Chemical Engineering Science, Journal Year: 2025, Volume and Issue: unknown, P. 121742 - 121742

Published: April 1, 2025

Language: Английский

Citations

0
Energetic Nitrated Azole Assemblies: Linear Alliance of Isomeric Furazan-1,2,4-triazole-pyrazole Combinations DOI
Igor L. Dalinger,

T. E. Khoranyan,

Kyrill Yu. Suponitsky

et al.

Crystal Growth & Design, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 19, 2024

While the effect of isomerism on properties energetic molecules has long been recognized, use this phenomenon to deliberately improve performance materials now approached. Here, we report development effective protocols for preparation isomeric compounds with a furazan-triazole-pyrazole framework, which differ in binding points these subunits and position nitro group. The two synthesized isomers readily form X-ray quality crystals solvates DMSO water, but only one isomer was able give unsolvated crystals. Significant differences molecular geometry noncovalent interactions due solvent incorporated into crystal lattice are highlighted. ambiguity evaluating structure–property relationships single compound from data its solvate is demonstrated. first time, 3-(5-(5-(3,4-dinitro-1H-pyrazol-5-yl)-1H-1,2,4-triazol-3-yl)-4-nitrofurazan (6), greater interest because, unlike other isomer, it not hygroscopic higher density. Isomer 6 shock sensitivity detonation velocity similar those RDX, more thermally stable insensitive friction.

Language: Английский

Citations

2