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

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

17
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

10
Polynitro-functionalized 4-phenyl-1H-pyrazoles as heat-resistant explosives DOI
Krishna Pandey, Prachi Bhatia,

Khwaja Mohammad

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(32), P. 6604 - 6616

Published: Jan. 1, 2023

This work demonstrates the synthesis, characterization, and energetic properties’ evaluation of polynitro-functionalized 4-phenyl-1 H -pyrazole-based heat-resistant explosives.

Language: Английский

Citations

21
Controlling the Energetic Properties of N-Methylene-C-Linked 4-Hydroxy-3,5-dinitropyrazole- and Tetrazole-Based Compounds via a Selective Mono- and Dicationic Salt Formation Strategy DOI
Prachi Bhatia, Krishna Pandey,

Badal Avasthi

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 15085 - 15096

Published: Oct. 17, 2023

In the quest to synthesize high-performing insensitive high-energy density materials (HEDMs), main challenge is establishing an equilibrium between energy and stability. For this purpose, we explored 4-hydroxy-3,5-dinitropyrazole- tetrazole-based energetic scaffolds connected via a N-methylene-C bridge. The hydroxy functionality nitro groups on pyrazole ring promotes physical stability inter- intramolecular hydrogen bonding contributes oxygen balance, supporting better performance. Due two acidic sites (OH NH) with different reactivities, series of monocationic dicationic salts were synthesized, their overall performance was compared. All compounds synthesized in study have high impact sensitivity >40 J friction >360 N. Monocationic generally found thermal respect corresponding salts, which showed salt formation strategy effectively improved 2 (Td = 168 °C), where most decomposition temperatures higher than 220 °C. characterized through IR, multinuclear NMR spectroscopy, high-resolution mass spectrometry (HRMS), elemental analysis. structure-property relationship studied using Hirshfeld surface analysis, noncovalent interaction (NCI) electrostatic potential studies.

Language: Английский

Citations

20
Bis(dinitropyrazolyl)methanes spruced up with hydroxyl groups: high performance energetic salts with reduced sensitivity DOI
Prachi Bhatia, Krishna Pandey, Priyanka Das

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(95), P. 14110 - 14113

Published: Jan. 1, 2023

Superior derivatives of bispyrazolylmethanes, bis(4-hydroxy-3,5-dinitropyrazolyl)methane and its high-performance energetic salts, were synthesized characterized.

Language: Английский

Citations

19
Taming of 4-azido-3,5-dinitropyrazole based energetic materials DOI Creative Commons
Priyanka Das, Prachi Bhatia, Krishna Pandey

et al.

Materials Advances, Journal Year: 2023, Volume and Issue: 5(1), P. 171 - 182

Published: Nov. 1, 2023

Energetic and physicochemical properties of 4-azido-3,5-dinitropyrazole based energetic compounds were fine-tuned by connecting it to 5-nitramino-1,2,4-oxadiazole moieties via N -methylene- C bridges salt formation strategy.

Language: Английский

Citations

18
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

9
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
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