Tunable Dimroth rearrangement of versatile 1,2,3-triazoles towards high-performance energetic materials

Feng, Shangbiao; Yin, Ping; He, Chunlin; Pang, Siping; Shreeve, Jean’ne M.

doi:10.1039/d1ta00109d

Cited by 75 publications

(34 citation statements)

References 25 publications

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“…From the discussion above, the Hirshfeld surface method possesses some advantages and has widely been applied in describing energetic compounds, − since our first introduction to establish IFS . First of all, it is adequate to straightforwardly describe intermolecular interactions, such as HB, π-stacking, and XB.…”

Section: Applicationmentioning

confidence: 99%

Hirshfeld Surface Method and Its Application in Energetic Crystals

Gou

et al. 2021

Crystal Growth & Design

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Understanding intermolecular interactions is fundamental to understanding the molecular stacking structures and some properties of energetic crystals, such as density, energy, mechanics, and sensitivity. The Hirshfeld surface method is a straightforward tool to reveal intermolecular interactions and nowadays has become increasingly popular in the field of energetic materials. This article highlights a wide range of applications of this method in describing intermolecular interactions including hydrogen bonding, π-stacking, halogen bonding, and lone pair−π (n−π) stacking, and molecular stacking patterns, and in predicting shear sliding characteristic and further impact sensitivity. Meanwhile, the roughness of the quantitative description of intermolecular interaction strength of the method, as a main shortcoming, is pointed out herein. Thus, this work is expected to guide the right and full use of the method. Besides, we present a perspective about using the Hirshfeld surface method to rapidly screen the molecular stacking mode and further impact sensitivity; thus, the fast screening of the two most important properties can be implemented, in combination with the existing mature energy prediction methods based on components. Thereby, a more reliable prediction procedure with an additional consideration of molecular stacking pattern will be produced, setting a basis for data-driven and crystal engineering research of energetic materials.

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Section: Applicationmentioning

confidence: 99%

Hirshfeld Surface Method and Its Application in Energetic Crystals

Gou

et al. 2021

Crystal Growth & Design

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“…The Hirshfeld surfaces clearly display the intermolecular or intramolecular interactions in the crystal stacking [32]. Figure 2b shows the two-dimensional (2D) fingerprint plots; in this case, the spikes for Compound 1 are broad, suggesting that a high percentage of hydrogen bonds are present.…”

Section: Hirshfeld Surfacementioning

confidence: 99%

“…In energetic compounds, the sensitivities are closely related to their surface ESPs. The larger electropositive areas and higher ESP values often result in high sensitivities [32,33]. Compound 1 exhibits lower ESP maximum values, especially in N-acetylamino group areas (+51.82 kcal⸱mol −1 ).…”

Section: Electrostatic Potentialmentioning

confidence: 99%

Nitration of Chitin Monomer: From Glucosamine to Energetic Compound

Dou

Zheng

et al. 2021

Molecules

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The nitration of chitin monomer in a mixture of nitric acid and acetic anhydride was conducted and a highly nitrated (3R,4R,6R)-3-acetamido-6-((nitrooxy)methyl)tetrahydro-2H-pyran-2,4,5-triyl trinitrate (1) was obtained. Its structure was fully characterized using infrared spectroscopy, NMR spectroscopy, elemental analysis, and X-ray diffraction. Compound 1 possesses good density (ρ: 1.721 g·cm−3) and has comparable detonation performance (Vd: 7717 m·s−1; P: 25.6 GPa) to that of nitrocellulose (NC: Vd: 7456 m·s−1; P: 23 GPa; Isp = 239 s) and microcrystalline nitrocellulose (MCNC; Vd: 7683 m·s−1; P: 25 GPa; Isp = 250 s). However, Compound 1 has much lower impact sensitivity (IS: 15 J) than the regular nitrocellulose (NC; IS: 3.2 J) and MCNC (IS: 2.8 J). Compound 1 was calculated to exhibit a good specific impulse (Isp: 240 s), which is comparable with NC (Isp: 239 s) and MCNC (Isp: 250 s). By replacing the nitrocellulose with Compound 1 in typical propellants JA2, M30, and M9, the specific impulse was improved by up to 4 s. These promising properties indicate that Compound 1 has a significant potential as an energetic component in solid propellants.

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“…1,2,3-Triazole nitro derivatives-five-membered heteroaromatic systems bearing three endocyclic nitrogen atoms and exocyclic explosophoric NO2 groups-are commonly used in the development of efficient high-energy compounds, including ionic ones, that exhibit enhanced technological and operational safety for various applications [9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Energetic Materials Based on N-substituted 4(5)-nitro-1,2,3-triazoles

et al. 2022

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The regularities and synthetic potentialities of the alkylation of 4(5)-nitro-1,2,3-triazole in basic media were explored, and new energetic ionic and nitrotriazole-based coordination compounds were synthesized in this study. The reaction had a general nature and ended with the formation of N1-, N2-, and N3-alkylation products, regardless of the conditions and reagent nature (alkyl- or aryl halides, alkyl nitrates, dialkyl sulfates). This reaction offers broad opportunities for expanding the variability of substituents on the nitrotriazole ring in the series of primary and secondary aliphatic, alicyclic, and aromatic substituents, which is undoubtedly crucial for solving the problems related to both high-energy materials development and medicinal chemistry when searching for new efficient bioactive compounds. An efficient methodology for the separation of regioisomeric N-alkyl(aryl)nitrotriazoles has been devised and relies on the difference in their basicity and reactivity during quaternization and complexation reactions. Based on the inaccessible N3-substitution products that exhibit a combination of properties of practical importance, a series of energy-rich ionic systems and coordination compounds were synthesized that are gaining ever-increasing interest for the chemistry of energy-efficient materials, coordination chemistry, and chemistry of ionic liquids.

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Tunable Dimroth rearrangement of versatile 1,2,3-triazoles towards high-performance energetic materials

Abstract: A highly efficient strategy of two different types of nitrogen-rich heterocyclic energetic compounds, featuring a single NH-bridge (-NH-) and a fused ring, was demonstrated by virtue of Dimroth rearrangement reactions...

Cited by 75 publications

References 25 publications

Hirshfeld Surface Method and Its Application in Energetic Crystals

Hirshfeld Surface Method and Its Application in Energetic Crystals

Nitration of Chitin Monomer: From Glucosamine to Energetic Compound

Energetic Materials Based on N-substituted 4(5)-nitro-1,2,3-triazoles

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