Research Of Energetic Compounds Based On Imidazole Analogous To LLM-116

In recent years,researchers are attracted by high nitrogen heterocyclic compounds for their excellent physicochemical properties.Among these,imidazole and tetrazole energetic compounds with the advantages of high nitrogen content,high formation enthalpy and stable structure of benzene have become an important topic in the field of energetic materials.Energetic compounds form intermolecular or intramolecular hydrogen bonds,which can significantly reduce sensitivity,increase density and enhance its detonation performance.Attributed to these properties,this paper was designed focusing on the following two aspects:(1)An amino group was introduced into a nitro-based energetic compound,which can form a hydrogen bond.The structural design of the high-energy insensitive energetic compound 4-amino-3,5-dinitropyrazole(LLM-116)is based on this concept.Among the energetic nitroimidazole compounds,2,4,5-trinitroimidazole(2,4,5-TNI)has good thermodynamic properties and excellent detonation performance;but its practical application was limited by the defect of its high sensitivity and strong acidity in the field of energetic materials.In this paper,2-amino-4,5-dinitroimidazole was the target of synthesis.However,after VNS amination and amino-substituted halogenation,the target product was not obtained,but 5-amino-4-nitro-2-chloroimidazole was synthesized for the first time.The new compound was characterized by infrared spectroscopy and mass spectrometry.Through the calculation and analysis of natural bond orbital theory,it was found that the C5 position of 4,5-dinitro-2-chloroimidazole was more susceptible to amino nucleophilic attack than the C2 site,which was consistent with the experimental results.(2)The oxime was introduced into azole energetic compounds,which can form a hydrogen bond.Di(1H-tetrazol-5-yl)methanone oxime exhibited good thermodynamic properties,low mechanical sensitivity and excellent detonation performance.In this paper,a novel method of preparing di(1H-tetrazol-5-yl)methane and then synthesizing di(1H-tetrazol-5-yl)methanone oxime was used,which achieved high purity.The structure of the product was characterized by infrared spectroscopy,mass spectrometry and nuclear magnetic carbon spectrum.