Design and synthesis of phenylene-bridged isoxazole and tetrazole-1-ol based energetic materials of low sensitivity

Lal, Sohan; Staples, Richard J.; Shreeve, Jean’ne M.

doi:10.1039/d3dt00166k

Cited by 9 publications

(6 citation statements)

References 37 publications

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“…Noncovalent interactions, including hydrogen bonds and π–π interactions, are commonly combined with decomposition temperatures ( T d ) to explain the thermal stability of energetic materials. − All materials in this study were dried before analysis to avoid the effects of crystal water (Figure ). The thermal stabilities of HNANTT, NANTT-ECPs, NANTT energetic salts, and NANTT co-crystal were measured by differential scanning calorimetry (DSC) with a heating rate of 5 K min –1 under a nitrogen atmosphere from 50 to 400 °C.…”

Section: Resultsmentioning

confidence: 99%

Increasing the Energy Limit of Single Triazole–Tetrazole: HNANTT Modified with Its Energetic Coordination Polymers, Co-Crystals, and Energetic Salts

Zhang

Xiao

Dong

et al. 2023

Crystal Growth & Design

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A series of novel energetic materials (EMs) based on a single triazole−tetrazole material, (Z)-N-(5-nitro-2-(1Htetrazol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-ylidene)nitramide (HNANTT) with tremendous physicochemical (d = 1.833 g cm −3 and ΔH f = 715.8 kJ mol −1 ) and energetic properties (D v = 9209 m s −1 and P = 36.38 GPa), were obtained. Detailed crystal structures of HNANTT and NANTT-5, 7, 8, 9, 11, and 13 were determined by single-crystal X-ray diffraction. Based on HNANTT, three kinds of energetic coordination polymers (ECPs) (NANTT-5, 7, and 8), four energetic salts (NANTT-9, 10, 11, and 12), and one energetic cocrystal (NANTT-13) were prepared and characterized to develop EMs with different kinds of advantages. By modifying HNANTT, all NANTT derivatives (except NANTT-10) showed good mechanical sensitivity (IS > 40 J, FS > 360 N), with NANTT-ECP-8 achieving the highest density (2.729 g cm −3 ) and thermal stability (287 °C), NANTT-12 has the highest detonation performances (D v = 9225 m s −1 and P = 30.87 GPa) among NANTT materials, while the NANTT co-crystal of 13 exhibited the best comprehensive performance, with superior detonation properties (D v = 9035 m s −1 and P = 30.12 GPa), higher thermal stability (236 °C), and N + O content of 83.2%.

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Section: Resultsmentioning

confidence: 99%

Increasing the Energy Limit of Single Triazole–Tetrazole: HNANTT Modified with Its Energetic Coordination Polymers, Co-Crystals, and Energetic Salts

Zhang

Xiao

Dong

et al. 2023

Crystal Growth & Design

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“…Isoxazoles, five-membered heterocyclic compounds containing adjacent nitrogen and oxygen atoms, have many applications including in photochromic components (Pu et al, 2011), liquid crystals (Kauhanka et al, 2006), solar cells (Yoon et al, 2022), high energy materials (Lal et al, 2023), pesticides and insecticides (Wang et al, 2022) and pharmaceuticals (Zhu et al, 2018). In a continuation of our previous work on isoxazole derivatives (Abdul Manan et al, 2023), we now present the synthesis and structure of the title compound.…”

Section: Structure Descriptionmentioning

confidence: 87%

Methyl 4-amino-3-methoxyisoxazole-5-carboxylate

2023

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The title compound, C6H8N2O4, a new derivative of isoxazole, has been synthesized and structurally characterized. The crystal structure shows the molecule to be almost planar (r.m.s. deviation for the non-hydrogen atoms = 0.029 Å), this conformation being supported by an intramolecular N—H...O hydrogen bond. In the extended structure, the molecules are linked by N—H...O hydrogen bonds into chains propagating along [010].

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“…Compared to oxadiazoles, oxazole-based energetic compounds have drawn less attention due to their lower nitrogen–oxygen content. − However, more modification sites in oxazole provide the possibility of introducing multifunctional groups. The methods of harmonic oscillator measure of aromaticity, bird aromaticity index, and multicenter bond order calculated by Multiwfn were employed to evaluate the aromaticity of oxazole and isoxazole, in which better aromaticity is always favorable for improved stability (the larger the value or the closer to 1, the stronger the aromaticity) (Figure b).…”

Section: Introductionmentioning

confidence: 99%

Improvement of Thermal Stability and Sensitivity of Furazan/Furoxan via Ring Closure Generation of Vicinal Amino-Nitro Structure

Zhang,

Zhang

et al. 2024

J. Org. Chem.

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Energetic compounds that display high thermal stability and insensitivity properties are essential for applications in mining, gas drilling, etc. In this work, a novel 4-nitro-5aminoisoxazole energetic moiety oriented to enhance thermal stability and decrease the sensitivity of furazan/furoxan analogues was constructed. The generation of a vicinal amino-nitro structure can be effectively realized in one step by a green and mild ringclosing reaction of nitroacetonitrile potassium salt with chloroxime in aqueous solution. Seven new energetic compounds with good thermal stability (T d : 155.8∼270.3 °C) and low sensitivity (IS: >40 J, FS: 96∼192 N) were synthesized. The nitro-furazan and isoxazole combined product exhibits the advantages of both skeletons, with energetic properties (D v = 8350 m s −1 , P = 30.1 GPa) that may find value in insensitive energetic materials. This strategy promises to achieve a balance between energy levels and stability of furazan/furoxan analogues and offers a new way for the design and synthesis of highly thermally stable compounds that meet special applications.

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Design and synthesis of phenylene-bridged isoxazole and tetrazole-1-ol based energetic materials of low sensitivity

Abstract: A variety of phenylene-bridged isoxazole and tetrazole-1-ol based green energetic materials was synthesized, for the first time, in good to excellent yields. The structures of the newly synthesized compounds were...

Cited by 9 publications

References 37 publications

Increasing the Energy Limit of Single Triazole–Tetrazole: HNANTT Modified with Its Energetic Coordination Polymers, Co-Crystals, and Energetic Salts

Increasing the Energy Limit of Single Triazole–Tetrazole: HNANTT Modified with Its Energetic Coordination Polymers, Co-Crystals, and Energetic Salts

Methyl 4-amino-3-methoxyisoxazole-5-carboxylate

Improvement of Thermal Stability and Sensitivity of Furazan/Furoxan via Ring Closure Generation of Vicinal Amino-Nitro Structure

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