First Alliance of Pyrazole and Furoxan Leading to High-Performance Energetic Materials DOI

T. E. Khoranyan,

Alexander А. Larin, Kyrill Yu. Suponitsky

et al.

ACS Applied Materials & Interfaces, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 25, 2024

Nitrogen heterocyclic scaffolds retain their leading position as valuable building blocks in material science, particularly for the design of small-molecule energetic materials. However, search more balanced combinations directly linked cores is far from being exhausted and aims to reach ideally high-energy substances. Herein, we present synthetic route novel pyrazole-furoxan framework enriched with nitro groups demonstrate a promising set properties, viz., good thermal stability, acceptable mechanical sensitivity, high detonation performance. In-depth crystal analysis showed that isomers having lower-impact sensitivity values both types regioisomeric pairs are those exocyclic furoxan oxygen atom closer pyrazole ring. Owing favorable combination densities (1.83-1.93 g cm

Language: Английский

Zwitterionic Energetic Materials: Synthesis, Structural Diversity and Energetic Properties DOI
Prachi Bhatia, Krishna Pandey, Dheeraj Kumar

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(17)

Published: June 10, 2024

Abstract Zwitterionic compounds are an emergent class of energetic materials and have gained synthetic interest many in the recent years. Due to their better packing efficiencies strong inter/intramolecular electrostatic interactions, they often ensue superior properties than salt analogues. A systematic review from perspective design, synthesis, physicochemical evaluation zwitterionic is presented. Depending on parent ring(s) used for synthesis type moieties bearing positive negative charges, different classes materials, such as primary explosives, secondary heat resistant oxidizers, etc., may result. The some also compared with analogous salts. This will encourage readers explore possibility designing new materials.

Language: Английский

Citations

13
A domino reaction from a sensitive azide: the impact of positional isomerism on chemical reactivity featuring ortho azido/nitro substituted derivatives DOI Creative Commons
Vikranth Thaltiri, Jatinder Singh, Richard J. Staples

et al.

Journal of Materials Chemistry A, Journal Year: 2024, Volume and Issue: 12(16), P. 9546 - 9551

Published: Jan. 1, 2024

This study highlights for the first time impact of positional isomerism on chemical reactivity which involves a domino reaction, salt formation, cyclization, and nucleophilic substitution.

Language: Английский

Citations

10
Single Step Synthesis of gem-Dinitro Methyl-1,2,4-triazole and Its Hydroxylamine Salt: An Alternative to the FOX-7 and Other Benchmark Explosives DOI
Parasar Kumar, Vikas D. Ghule, Srinivas Dharavath

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4788 - 4792

Published: May 29, 2024

gem-Dinitro methyl based high-energy-density material 5-(dinitromethylene)-4,5-dihydro-1H-1,2,4-triazole (2) and its hydroxylamine salt (4) were synthesized for the first time in a single step characterized. Further, structure of 2 was confirmed by single-crystal X-ray diffraction (SCXRD) studies. Interestengly, both compounds show excellent density (> 1.83 g cm-3), detonation velocity 8700 m s–1), pressure 30 GPa) are insensitive toward mechanical stimuli such as impact friction sensitivity. Considering their synthetic fesibility balanced energetic performance, 4 future prospects potential next-generation materials replacenent many presently used benchmark high energy RDX, FOX-7 highly H-FOX.

Language: Английский

Citations

10
N-Acetonitrile functionalized 3-nitrotriazole: Precursor to nitrogen rich stable and insensitive energetic materials DOI Creative Commons
Prachi Bhatia,

Peddapothula Sahithi Priya,

Priyanka Das

et al.

Energetic Materials Frontiers, Journal Year: 2024, Volume and Issue: 5(1), P. 8 - 16

Published: Feb. 23, 2024

In the field of energetic materials, prime attention has been given to synthesis environmentally compatible materials having an adequate balance between energy and stability. For this purpose, nitrogen-rich heterocyclic rings have contributed as pivotal frameworks. Nitro-functionalized 1,2,4-triazoles profusely used a constituent for synthesizing high-performing (EMs) due their high nitrogen content, good thermal stability, modifiable sites via functionalization. Combination with different scaffold may provide opportunity accessible tailoring. work, in effort investigate potential 3-nitrotriazoles, its N-acetonitrile derivative 2 was synthesized, which further converted various explosophores. N-methylene-C bridged asymmetrically connected tetrazole (3) 1,2,4-oxadiazole (9 10) based EMs synthesized. Further tuning properties salt formation strategy employed compounds 4–7, 11 12. 1,2,4-oxadiazole-based compound 9 also confirmed X-ray diffraction analysis, 10 analyzed 15N NMR spectroscopy. Compounds 3, 4, 5, 7 exhibited stabilities were found be insensitive towards impact friction. 6, detonation performance comparable conventional explosive TATB.

Language: Английский

Citations

9
Insights into Structural and Energetic Features of 3,5-Dinitropyrazole-4-carboxylic Acid and Its Energetic Salts DOI
Krishna Pandey, Priyanka Das, Prachi Bhatia

et al.

Crystal Growth & Design, Journal Year: 2024, Volume and Issue: 24(16), P. 6790 - 6799

Published: July 31, 2024

The dominance of nitro pyrazole-based explosives in the recently reported high-performing energetic materials motivated us to comprehensively investigate energy–stability correlation among different compounds based on 3,5-dinitro pyrazoles employing various computational methods. We also explored and physicochemical properties overlooked compound 3,5-dinitropyrazole-4-carboxylic acid (CDNP). This study revealed that CDNP exhibits highest thermal stability 4-substituted-3,5-dinitropyrazoles, combined with an acceptable performance. These characteristics are attributed its layered packing, strong intermolecular interactions, carbonyl bonds. Furthermore, dicationic salt formation further allowed fine-tune overall performance stability. dihydroxylammonium (5) shows best performance, comparable well-known traditional explosive TATB, good low sensitivity toward impact friction.

Language: Английский

Citations

8
Time for mixing: Mixed dicationic energetic salts based on methylene bridged 4-hydroxy-3,5-dinitropyrazole and tetrazole for tunable performance DOI Creative Commons
Prachi Bhatia, Vikas D. Ghule, Dheeraj Kumar

et al.

Energetic Materials Frontiers, Journal Year: 2024, Volume and Issue: 5(2), P. 105 - 111

Published: May 14, 2024

Various types of materials have been explored in the pursuit high energy density (HEDMs) that balanced and stability. Among them, energetic salts show numerous advantages, such as lower vapor pressures, physical stabilities, opportunity for favourable tuning by careful selection cations/anions. Nitrogen-rich bases are generally used cations salt formation. While synthesis with larger lowers sensitivity, smaller aid better performance. A combination both same ionic moieties might help formation a superior explosive. In this work, facile route mixed dicationic based on 1-((1H-tetrazol-5-yl)methyl)-3,5-dinitro-1H-pyrazol-4-ol (compound 1) has various combinations bigger (compounds 4-10). All synthesized showed positive heats formation, performance comparable to TATB, excellent stability towards impact friction, acceptable thermal stabilities. This improved technique will provide an additional option fine-tuning properties HEDMs facilitate exploring role overall compounds.

Language: Английский

Citations

7
Combination of N‐amino‐1,2,4‐triazole and 4‐hydroxy‐3,5‐dinitropyrazole for the synthesis of high performing explosives DOI
Prachi Bhatia,

Pooja Jangra,

Vikas D. Ghule

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(8), P. 1299 - 1305

Published: June 5, 2024

Abstract In an attempt to cultivate energy‐stability balance, a series of nitrogen and oxygen‐rich high energy density materials were synthesized based on N ‐substituted 4‐hydroxy‐3,5‐dinitropyrazole methylene‐linked ‐amino‐1,2,4‐bridges. The hydroxy substituent contributed oxygen content, hydrogen bonding, tunability via salt formation. On the other hand, triazole bridge delivered content thermal stability. All compounds characterized with multinuclear NMR, FTIR, HRMS, elemental analysis, their physicochemical energetic properties analyzed. Energetic 1 – 5 showed detonation performance adequate overall stabilities. Compound exhibited higher (1.84 g/cm 3 ) ( D v = 8103 m/s, P 26.9 GPa) in comparison its reported amino derivative.

Language: Английский

Citations

5
N-Methylene-C-Linked Nitropyrazoles and 1,2,4-Triazolone-3-one: Thermally Stable Energetic Materials with Reduced Sensitivity DOI
Krishna Pandey, Priyanka Das,

Meera Khatri

et al.

Dalton Transactions, Journal Year: 2024, Volume and Issue: 53(42), P. 17179 - 17189

Published: Jan. 1, 2024

A family of new asymmetric N -methylene-C linked nitropyrazoles and 1,2,4-triazol-3-one based thermally stable energetic materials with reduced sensitivity has been synthesized. Background image via Canva.

Language: Английский

Citations

4
N‐Alkylation of 4‐Hydroxy‐3,5‐Dinitropyrazole: A Facile Route for the Synthesis of Insensitive Energetic Materials DOI Open Access
Prachi Bhatia, Priyanka Das, Dheeraj Kumar

et al.

Propellants Explosives Pyrotechnics, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 4, 2025

ABSTRACT Behind the synthesis of any new high‐energy density material is objective to achieve equilibrium between energy and stability, which becomes laborious because their adversarial nature. Nitropyrazoles, with viable syntheses easy modifiability, have been adopted typically as backbones this goal. However, acidic nature pyrazole N H in nitropyrazoles limits usefulness despite exhibiting appealing characteristics. 4‐Hydroxy‐3,5‐dinitropyrazole (HODNP) an interesting skeleton presence hydroxy functionality two nitro groups, not only provides additional oxygen content for better output but also possesses quality strong hydrogen bonding interactions tuning properties via salt formation. N‐alkylation most straightforward technique protection unwanted proton, addition making them more physically stable. In work, we synthesized ‐methylated , N’ ‐ethylene‐bridged derivatives ( 2 7 ) HODNP. Mono dicationic salts 3 ‐ 6 8 11 were boost performance further. N‐methylated neutral compound its ammonium confirmed through 15 NMR analysis, was single‐crystal analysis. All compounds showed excellent physical stability (IS >40 J, FS > 360 N), good thermal (T d 180°C). The detonation characteristics found be similar ones 1,3,5‐triamino‐2,4,6‐trinitrobenzene (D v = 7704–8172 m/s, p 22.4–27.3 GPa).

Language: Английский

Citations

0
Low-sensitivity energetic material based on 1,2,4-oxadiazole DOI Creative Commons
Gan Jin,

Caijin Lei,

Jie Tang

et al.

FirePhysChem, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 1, 2024

In this work, a new series of monocyclic compounds based on 1,2,4-oxadiazol-5(4H)-one was synthesized. The molecular structure, thermal stability and sensitivity to external stimuli for these were characterized by X-ray diffraction analysis, NMR (1H 13C) spectroscopy, IR differential scanning calorimetry (DSC) the standard BAM method. Compound 3-((2,2,2-trinitroethyl) amino)-1,2,4-oxadiazol (3) with trinitromethyl exhibits higher decomposition temperature (Td = 143°C) than that 3-(dinitromethyl)-1,2,4-oxadiazol-5-one (4) 76°C) reported in literature. addition, compound 3 lower impact sensitivities (IS) (IS 10 J) 4, N3-(2,2,2-Trinitroethyl)-1,2,4-oxadiazole-3,5-diamine (5) RDX (4: 6 J; 5: RDX: 7.4 J). Charge distribution Hirshfeld surface calculated make further research intermolecular interaction trinitromethyl. difference is mainly due existence hydrogen bonds. These results indicate has promising application prospects as energetic material.

Language: Английский

Citations

2