Effectively improving the energy of monocyclic imidazoles to a high level by the introduction of bridge-rings and nitro groups through different kinds of Diels–Alder reactions: a DFT study,Molecular Systems Design & Engineering

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Effectively improving the energy of monocyclic imidazoles to a high level by the introduction of bridge-rings and nitro groups through different kinds of Diels–Alder reactions: a DFT study
Molecular Systems Design & Engineering ( IF 3.2 ) Pub Date : 2020-10-19 , DOI: 10.1039/d0me00075b
Qiong Wu _{1,

2,

3,

4,

5} , Qinnan Hu _{1,

2,

3,

4,

5} , Mingquan Li _{1,

2,

3,

4,

5} , Zewu Zhang _{1,

2,

3,

4,

5} , Weihua Zhu _{5,

6,

7,

8}

Affiliation

In this work, the classic Diels–Alder reaction was employed to improve the energy of traditional existing monocyclic imidazole-based energetic compounds to a high level. The direction, type and energy barrier of the reaction between six imidazole dienes and six NO₂/NH₂-substituted ethylene/acetylene dienophiles were investigated by density functional theory and molecular orbital theory. Six dienophiles could react with six dienes through the normal, inverse or neutral Diels–Alder reaction at different energy barriers. 1,2-Dinitroethylene is the optimal dienophile that could react with dienes easily through the neutral Diels–Alder reaction. Five dienes were picked out to react with 1,2-dinitroethylene and tetranitroethylene to form seven new bridge-ring energetic compounds. The calculations on the performance of these seven compounds showed that they possess high density, oxygen balance and heat of formation. As a result, from the corresponding dienes to the new designed bridge-ring energetic compounds, the energy was increased from a mediocre level to a high level successfully, due to the appropriate introduction of bridge-rings and nitro groups into the monocyclic structure by the Diels–Alder reaction. Four compounds even have a comparable detonation velocity with one very powerful high energy compound 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane. Unexpectedly, compared to that of the dienes, the sensitivity was also improved to some degree. This work may be helpful for the design and synthesis of new advanced bridge-ring high energy compounds.

中文翻译：

通过不同类型的狄尔斯-阿尔德反应引入桥环和硝基，有效提高单环咪唑的能量至高水平：DFT研究

在这项工作中，经典的Diels-Alder反应被用于将传统的现有单环咪唑基高能化合物的能量提高到较高水平。六个咪唑二烯与六个NO ₂ / NH ₂反应的方向，类型和能垒通过密度泛函理论和分子轨道理论研究了取代的乙烯/乙炔双亲亲烯。六个亲双烯体可以在不同的能垒下通过正态，逆或中性Diels-Alder反应与六个二烯反应。1,2-二硝基乙烯是最佳的亲二烯体，可以通过中性的狄尔斯-阿尔德反应轻松地与二烯反应。挑选出五个二烯与1,2-二硝基乙烯和四硝基乙烯反应形成七个新的桥环高能化合物。对这七种化合物的性能的计算表明，它们具有高密度，氧平衡和形成热。结果，从相应的二烯到新设计的桥环高能化合物，能量成功地从中等水平提高到了高水平，由于通过Diels-Alder反应将桥环和硝基适当地引入单环结构。四种化合物甚至具有与一种非常强大的高能化合物2,4,6,8,10,12-六硝基-2,4,6,8,10,12-六氮杂异纤锌矿型结构烷烃相比的爆炸速度。出乎意料的是，与二烯相比，灵敏度也有所提高。这项工作可能有助于新的先进桥环高能化合物的设计和合成。

更新日期：2020-11-06

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