立体化学和区域化学对高能材料的影响。
Impact of Stereo- and Regiochemistry on Energetic Materials.
机构信息
Department of Chemistry , Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Energetics Synthesis & Formulation Branch , CCDC U.S. Army Research Laboratory , Aberdeen Proving Ground , Maryland 21005 , United States.
出版信息
J Am Chem Soc. 2019 Aug 14;141(32):12531-12535. doi: 10.1021/jacs.9b06961. Epub 2019 Aug 5.
Abstract
The synthesis, physical properties, and calculated performances of six stereo- and regioisomeric cyclobutane nitric ester materials are described. While the calculated performances of these isomers, as expected, were similar, their physical properties were found to be extremely different. By alteration of the stereo- and regiochemistry, complete tunability in the form of low- or high-melting solids, stand-alone melt-castable explosives, melt-castable explosive eutectic compounds, and liquid propellant materials was obtained. This demonstrates that theoretical calculations should not be the main factor in driving the design of new materials and that stereo- and regiochemistry matter in the design of compounds of potential relevance to energetic formulators.
摘要
描述了六种立体和区域异构体环丁烷硝酸酯材料的合成、物理性质和计算性能。虽然这些异构体的计算性能如预期的那样相似，但它们的物理性质却截然不同。通过改变立体和区域化学，可以获得从低熔点固体到高熔点固体、独立的可熔铸炸药、可熔铸炸药共晶化合物和液体推进剂材料等形式的完全可调性。这表明理论计算不应成为推动新材料设计的主要因素，而立体和区域化学在设计对高能配方有潜在意义的化合物时很重要。
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3
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