N-Acetonitrile Functionalized Nitropyrazoles: Precursors to Insensitive Asymmetric N-Methylene-C Linked Azoles

被引：51

作者：

Kumar, Dheeraj ^{[1
]}

Imler, Gregory H. ^{[2
]}

Parrish, Damon A. ^{[2
]}

Shreeve, Jean'ne M. ^{[1
]}

机构：

[1] Univ Idaho, Dept Chem, Moscow, ID 83844 USA

[2] Naval Res Lab, 4555 Overlook Ave, Washington, DC 20375 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 33期

关键词：

detonation properties; energetic materials; methylene-bridged; nitropyrazoles; tetrazoles; HIGH-ENERGY-DENSITY; METAL-ORGANIC FRAMEWORK; HIGH-PERFORMANCE; DERIVATIVES; DESIGN; SALTS; SENSITIVITY; IMPACT;

D O I：

10.1002/chem.201700786

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Properties of energetic compounds obtained by linking energetic pyrazoles to tetrazoles by means of N-methylene-C bridges can be fine-tuned. Reactions of pyrazole derivatives with chloroacetonitrile followed by conversion of the cyano group to tetrazole using click reactions in the presence of zinc chloride result in asymmetric N-methylene-C bridged azole-based energetic compounds. All the compounds were thoroughly characterized by IR and NMR [H-1, C-13 {H-1}, N-15] spectroscopy, elemental analysis, and differential scanning calorimetry (DSC), and for two compounds, further supported by single-crystal X-ray diffraction studies. Heats of formation and detonation performances were calculated using Gaussian 03 and EXPLO5 v6.01 programs, respectively. Initial studies show that this new approach is promising for synthesizing less sensitive energetic compounds with finetuned properties.

引用

页码：7876 / 7881

页数：6

共 69 条

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