Exploring the explosive potential of 2,3-dihydrofuran derivatives as novel insensitive high-energy density materials

IF 2.1 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Molecular Modeling Pub Date : 2025-03-05 DOI:10.1007/s00894-025-06334-7

Fasila P. M., Rahana Ameen, Biju A. R.

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引用次数: 0

Abstract

Context

In this study, a series of carefully designed oxygen-rich bicyclic ozonides, derived from 2,3-dihydrofuran (2,6,7,8-tetraoxabicyclo[3.2.1]octane), have been studied with meticulous attention to the incorporation of nitro and/or trinitromethyl (TNM) substituents. These compounds exhibit significant promise as high-energy–density materials (HEDMs), thus representing a pioneering avenue in the realm of advanced energetic materials. Evaluating the energetic performances and impact sensitivity is the focus of our theoretical calculations. The majority of the designed compounds exhibit elevated density, complemented by outstanding detonation properties. Each of these compounds demonstrates a high positive heat of formation, with many of them displaying impact sensitivities well suited for applications in high-energy density materials (HEDMs). Due to their significant oxygen content, all 45 designed compounds maintain a high positive oxygen balance. This unique combination of high-performance characteristics and low sensitivities positions them as promising candidates for high-energy explosives. Notably, among the compounds, FOZ23 (3-nitro-5-(trinitromethyl)-2,6,7,8-tetraoxabicyclo[3.2.1]octane), FOZ19 (3-nitro-4-(trinitromethyl)-2,6,7,8-tetraoxabicyclo[3.2.1]octane), and FOZ24 (1-nitro-5-(trinitromethyl)-2,6,7,8-tetraoxabicyclo[3.2.1]octane) exhibit exceptional performance and sensitivities, warranting further investigation and consideration. From the analysis of BDE of C-NO₂ and O–O linkages, it was found that the peroxide bond is stronger than C-NO₂ bond. Therefore, peroxides can be used for various applications in the nearby future by incorporating proper substitutions.

Methods

Gaussian 09 program was used for geometry optimization and vibrational frequency analysis of the selected compounds. The method employed for the study was density functional theory at the B3LYP level of approximation using aug-cc-pVDZ as the basis set. Multiwfn program was employed for Electrostatic potential analysis.

Graphical abstract

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探索2,3-二氢呋喃衍生物作为新型不敏感高密度材料的爆炸潜力

在本研究中，精心设计了一系列由2,3-二氢呋喃（2,6,7,8-四氧杂环[3.2.1]辛烷）衍生的富氧双环臭氧化合物，并对硝基和/或三硝基甲基（TNM）取代基的掺入进行了细致的研究。这些化合物作为高能量密度材料（HEDMs）具有重要的前景，因此代表了先进高能材料领域的开创性途径。能量性能和冲击灵敏度的评估是理论计算的重点。大多数设计的化合物具有较高的密度，并具有出色的爆轰性能。这些化合物中的每一种都表现出很高的正形成热，其中许多化合物表现出非常适合应用于高能量密度材料（hedm）的冲击灵敏度。由于其显著的氧含量，所有45种设计的化合物保持高正氧平衡。这种高性能特性和低灵敏度的独特组合使它们成为高能炸药的有希望的候选者。值得注意的是，在这些化合物中，FOZ23（3-硝基-5-（三硝基甲基）-2,6,7,8-四氧沙环[3.2.1]辛烷）、FOZ19（3-硝基-4-（三硝基甲基）-2,6,7,8-四氧沙环[3.2.1]辛烷）和FOZ24（1-硝基-5-（三硝基甲基）-2,6,7,8-四氧沙环[3.2.1]辛烷）表现出优异的性能和灵敏度，值得进一步研究和考虑。通过对C-NO2和O-O键的BDE分析，发现过氧化物键比C-NO2键强。因此，在不久的将来，通过加入适当的取代，过氧化物可以用于各种应用。方法采用高斯09程序对所选化合物进行几何优化和振动频率分析。研究方法为B3LYP近似水平的密度泛函理论，以aug-cc-pVDZ为基集。采用Multiwfn程序进行静电电位分析。图形抽象

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来源期刊

Journal of Molecular Modeling 化学-化学综合

CiteScore

3.50

自引率

4.50%

发文量

362

审稿时长

2.9 months

期刊介绍： The Journal of Molecular Modeling focuses on "hardcore" modeling, publishing high-quality research and reports. Founded in 1995 as a purely electronic journal, it has adapted its format to include a full-color print edition, and adjusted its aims and scope fit the fast-changing field of molecular modeling, with a particular focus on three-dimensional modeling. Today, the journal covers all aspects of molecular modeling including life science modeling; materials modeling; new methods; and computational chemistry. Topics include computer-aided molecular design; rational drug design, de novo ligand design, receptor modeling and docking; cheminformatics, data analysis, visualization and mining; computational medicinal chemistry; homology modeling; simulation of peptides, DNA and other biopolymers; quantitative structure-activity relationships (QSAR) and ADME-modeling; modeling of biological reaction mechanisms; and combined experimental and computational studies in which calculations play a major role.