Oxygen Enriched Oxamides and N-Dinitrated Oxamides: Trinitroethyl Esters, Nitrocarbamates and Nitrates,ChemistrySelect

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Oxygen Enriched Oxamides and N-Dinitrated Oxamides: Trinitroethyl Esters, Nitrocarbamates and Nitrates
ChemistrySelect ( IF 1.9 ) Pub Date : 2021-09-01 , DOI: 10.1002/slct.202102271
Thomas M. Klapötke ₁ , Burkhard Krumm ₁ , Thomas Reith ₁ , Christian Riedelsheimer ₁

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Starting from the readily available starting materials diethyl oxalate, glycine and β-alanine, some new N-nitrated oxamides were synthesized. Oxamides formed by condensation reactions were subsequently nitrated to form the corresponding dinitroxamides. These were further converted to the corresponding acid chlorides with the utilization of thionyl chloride. The final reaction of the β-alanine based dinitroxamide with trinitroethanol generated the energetic target ester in moderate yield and high purity. Additionally, starting from diethyl oxalate and ethanolamine gave access to a nitrocarbamate based on an oxamide. Furthermore, the previously reported compound bis(2-nitratoethyl) oxamide was synthesized now in a more facile fashion and fully characterized, especially in case of the energetic properties, sensitivities and crystal structure. The compounds were fully analysed by NMR spectroscopy, vibrational analysis and elemental analysis. The heat of formation was calculated with the Gaussian program package and in combination with the experimental density the energetic properties were estimated utilizing the Explo5 computer code.

中文翻译：

富氧草酰胺和 N-二硝化草酰胺：三硝基乙酯、硝基氨基甲酸酯和硝酸盐

从容易获得的起始原料草酸二乙酯、甘氨酸和 β-丙氨酸开始，一些新的N合成了-硝化草酰胺。通过缩合反应形成的草酰胺随后被硝化以形成相应的二硝基酰胺。利用亚硫酰氯将这些进一步转化为相应的酰氯。β-丙氨酸基二硝基酰胺与三硝基乙醇的最终反应以中等产率和高纯度生成了高能目标酯。此外，从草酸二乙酯和乙醇胺开始得到基于草酰胺的硝基氨基甲酸酯。此外，先前报道的化合物双（2-硝基乙基）草酰胺现在以更容易的方式合成并得到充分表征，特别是在能量特性、敏感性和晶体结构的情况下。通过核磁共振光谱、振动分析和元素分析对化合物进行了全面分析。Explo 5 计算机代码。

更新日期：2021-09-01

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