Polynitro-Functionalized Dipyrazolo-1,3,5-triazinanes: Energetic Polycyclization toward High Density and Excellent Molecular Stability,Angewandte Chemie International Edition

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Polynitro-Functionalized Dipyrazolo-1,3,5-triazinanes: Energetic Polycyclization toward High Density and Excellent Molecular Stability
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2017-06-19 06:55:53 , DOI: 10.1002/anie.201704687
Ping Yin ₁ , Jiaheng Zhang ₂ , Gregory H. Imler ₃ , Damon A. Parrish ₃ , Jean'ne M. Shreeve ₁

Affiliation

A new fused N-heterocyclic framework, dipyrazolo-1,3,5-triazinane, was synthesized and the physiochemical properties of its derivatives were investigated to evaluate the integrated energetic performance. In contrast to 1,3,5-trinitro-1,3,5-triazinane (RDX) featuring a distorted chair confirmation, polynitro-functionalized dipyrazolo-1,3,5-triazinanes have nearly planar backbones, thereby enhancing the density and thermal stability. Among these new energetic tricyclic compounds, 5 a and 12 show favorable crystal densities of 1.937 g cm⁻³ and 1.990 g cm⁻³ at 150 K, respectively, which rank highest in triazinane-based energetic compounds. Additionally, this synthetic approach was carried out to form seven-membered and eight-membered rings, giving rise to tetranitro dipyrazolo-1,3,5-triazepane (5 b) and tetranitro dipyrazolo-1,3,5-triazocane (5 c), respectively.

中文翻译：

多硝基功能化Dipyrazolo-1,3,5-triazinanes：朝着高密度和出色的分子稳定性的能量多环化。

合成了一个新的稠合的N-杂环骨架，双吡唑-1,3,5-三嗪烷，并对其衍生物的理化性质进行了研究，以评估其综合的能量性能。与1,3,5-trinitro-1,3,5-triazinane（RDX）具有扭曲的座椅确认特征相反，多硝基官能化的diyrazolo-1,3,5-triazinanes具有几乎平坦的骨架，从而提高了密度和散热性稳定。在这些新的高能三环化合物中，5a和12显示出1.937 g cm ^-3和1.990 g cm ^-3的有利晶体密度。在150 K下，分别在基于三嗪烷的高能化合物中排名最高。此外，进行了这种合成方法以形成七元和八元环，从而产生了四硝基双吡唑-1,3,5-三氮杂庚烷（5 b）和四硝基双吡唑-1,3,5-三唑烷（5 c），分别。

更新日期：2017-06-20

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