Theoretical investigation on the intermolecular interactions between 3-nitro-1,2,4-triazol-5-one and 2,6-diamino-3,5-dinitropyrazine-1-oxide using DFT methods

Hu, Wenjun; Gou, Ruijun; Zhang, Shuhai; Liu, Yang; Shang, Fengqin; Chen, Yahong; Bai, Hui

doi:10.1007/s11696-021-02059-y

Cited by 12 publications

(6 citation statements)

References 45 publications

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“…Even at the end of the thermolysis simulation, the resulting products are relatively stable. There is one specific case in which H 2 O molecules decompose at high temperatures, as shown in eqn (15). This process may, at least in theory, be carried out in reverse absolutely.…”

Section: Analysis Of Thermolysis Products and Chemical Bondsmentioning

confidence: 99%

“…In particular, NTO's strong acidity (pK a = 3.76) is a major issue that has to be highlighted. 14 In light of this issue, Hu et al 15 investigated the interaction between NTO and 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105) based on Density Functional Theory (DFT). Based on the findings, it was determined that NTO and LLM-105 formed a strong hydrogen bond, which neutralized the acidity of the compounds.…”

Section: Introductionmentioning

confidence: 99%

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Multi-aspect simulation insight on thermolysis mechanism and interaction of NTO/HMX-based plastic-bonded explosives: a new conception of the mixed explosive model

Yuan

Ying

Zhang

et al. 2023

Phys. Chem. Chem. Phys.

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Section: Analysis Of Thermolysis Products and Chemical Bondsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Multi-aspect simulation insight on thermolysis mechanism and interaction of NTO/HMX-based plastic-bonded explosives: a new conception of the mixed explosive model

Yuan

Ying

Zhang

et al. 2023

Phys. Chem. Chem. Phys.

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“…RDG analysis is used to visualize interactions in crystal structures, including π•••π noncovalent interactions. 49 In the AIM theory, the electron density at the interaction critical point is one of the most significant indicators to determine the interaction strength, and its values are positively correlated with the bond strength. To further understand the nature of the interactions in the crystal structures, AIM and RDG analyses were performed on the multicomponent crystals.…”

Section: Conformation and Packing Similarity Analysismentioning

confidence: 99%

New Insights into the Solubilization of Multicomponent Crystals: A Case Study of Pipemidic Acid

Xiao

Jing³

et al. 2023

Crystal Growth & Design

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Pipemidic acid (PPA), one of the most prominent medications of the second generation of quinolones, has broadspectrum antibacterial activity. Due to its low solubility and short half-life, it has led to a poor efficacy and numerous side effects. Multicomponent crystals have been proven to be an effective strategy for tuning the dissolution property of pharmaceuticals. Herein, multicomponent crystals of PPA with salicylic acid (SAA), gentian acid (GA), protocatechuic acid (PCA), caffeic acid (CAA), and saccharin (SAC) were synthesized. All the multicomponent crystals were characterized by single crystal X-ray diffraction (SCXRD), powder X-ray diffraction (PXRD), and thermal analysis including differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Hirshfeld Surface (HS) analysis showed that compared with PPA trihydrate, the contribution of the strong interaction in the multicomponent crystal structure to maintain the crystal structure tended to be weakened, indicating that the multicomponent crystal may increase the apparent solubility of PPA. Moreover, all the multicomponent crystals exhibit increased solubility and decelerated intrinsic dissolution rate (IDR). Specifically, the PPA-SAA and PPA-GA salts demonstrate the most significant solubility improvement in the pH 6.8 buffer by 640.98% and 213.11% when compared to the pure PPA trihydrate, respectively. For the other hydrates of the three salts (PPA-PCA salt hydrate, PPA-CAA salt hydrate, and PPA-SAC salt hydrate), the solubility increased by 45.90%, 13.11%, and 165.57%, respectively. Further, in vitro dissolution experiment results revealed that the IDR values of the multicomponent crystals (PPA-SAA salt, PPA-GA salt, PPA-PCA salt hydrate, PPA-CAA salt hydrate, and PPA-SAC salt hydrate) were 2.40, 2.14, 1.57, 1.53, and 2.80 mg/cm 2 /min, respectively, which were all less than that of the PPA trihydrate (5.24 mg/cm 2 /min). This causes the multicomponent crystals to release at a slower rate, thus improving bioavailability. Molecular dynamics simulation results indicate that the solubilizing effect is caused by the lower lattice energy and full exposure of hydrophilic groups caused by molecular assembly. Different from the cyclic supramolecular synthons in other multicomponent crystals from structure point, the ones in PPA-SAA salts are chain-like synthons, which may be one of the main reasons for the most significant increase in its apparent solubility. Stability tests showed that all multicomponent crystals exhibited excellent stability over 8 weeks at accelerated storage conditions (40 °C and 75% RH). This work demonstrates that multicomponent crystals can offer a promising potential to slow the release rate and enhance the solubility for these defective pharmaceuticals.

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“…Therefore, theoretical calculations have become a common part of energetic materials research. 4–6 In the case of DFT and AIMD methods, which are considered to be able to accurately describe atoms and electrons, these methods have been used in various fields of energetic materials research, such as intermolecular interactions between explosives, 7–10 impact behavior of plastic bonded explosives (PBX), 11 thermal decomposition of explosive molecules or crystal, 12–15 and crystal structure. 16 These research methods have been proven to be effective and reliable, and can even obtain theories that are difficult to be achieved by experiments alone, which will provide guidance for the design and understanding of the internal mechanism of energetic materials in the future.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, many researchers have studied the binding ability and performance improvement of NTO with other energetic materials, such as HMX, 26,27 TZTN, 28,29 CL-20, 30 and LLM-105. 8…”

Section: Introductionmentioning

confidence: 99%

Theoretical investigation on intermolecular interactions, co-crystal structure, thermal decomposition mechanism, and shock properties of 3-nitro-1,2,4-triazol-5-one (NTO) and ammonium perchlorate

Chai

Shu

et al. 2023

CrystEngComm

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Theoretical investigation on the intermolecular interactions between 3-nitro-1,2,4-triazol-5-one and 2,6-diamino-3,5-dinitropyrazine-1-oxide using DFT methods

Cited by 12 publications

References 45 publications

Multi-aspect simulation insight on thermolysis mechanism and interaction of NTO/HMX-based plastic-bonded explosives: a new conception of the mixed explosive model

Multi-aspect simulation insight on thermolysis mechanism and interaction of NTO/HMX-based plastic-bonded explosives: a new conception of the mixed explosive model

New Insights into the Solubilization of Multicomponent Crystals: A Case Study of Pipemidic Acid

Theoretical investigation on intermolecular interactions, co-crystal structure, thermal decomposition mechanism, and shock properties of 3-nitro-1,2,4-triazol-5-one (NTO) and ammonium perchlorate

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