碱性介质中芳醚键的稳定性研究-应用化学专业论文.docxVIP

摘 摘 要 取代芳基醚这类化合物，是合成染料、医药、农药等的重要中间体。研究它们的 稳定性对合成这类化合物有重要意义。本文选用硝基作为强吸电子基团，设计合成了 一系列的芳醚衍生物作为研究对象，考察了它们的芳醚键在碱性介质中的稳定性情 况。 本文工作分成两大部分：首先合成了纯度较高的对硝基芳基醚、邻硝基芳基醚、 芳基醚、对甲基芳基醚这四大系列的芳醚化合物，利用高效液相色谱测定产物的纯度， 用毛细管法测定熔点，1H-NMR核磁共振仪确定了结构。然后再以这些化合物为反应 底物，在碱性条件下进行反应。选用对硝基甲苯为内标，用高效液相色谱仪对芳醚键 断裂的程度进行定量分析，计算出原料的转化率。 实验结果表明，含-N02的取代芳基醚，在碱性溶液中，易发生亲核取代反应， 从而使芳醚键断裂。碱浓度越高，反应温度越高，反应时间越长，亲核试剂的活性越 强，醚键断裂的程度越大，这类化合物就越不稳定。发现一系列芳氧丙酸化合物发生 亲核取代反应的异常情况，推测可能是分子内邻基参与的亲核取代反应。 关键词：芳醚，硝基，碱性介质，芳醚键的断裂 AbstractSubstituted Abstract Substituted aryl ethers are the key intermediate compounds to synthesize dye、 medicine、pesticide and SO on．It is of very importance tO study their stability for synthesizing these compounds A series ramification of aryl ethers that containing strong electrowithdrawing group(-N02)have been synthesized，which were used as the studied substrate and the stability ofaryl aherbond in the alkaline medium has been researched． The project is divided into two parts：Firstly,four kinds of aryl ethers have been synthesized，which are p-nitro aryl ethers，D—nitro aryl ethers，phenyl ethers，p-methyl aryl ethers．The content of these objective products has been determined by high performance liquid chromatography,the melting point has been measured by capillary tube method， their structures have been confirmed by‘H-NMR spectra Secondly,these compounds were used as substrate to take place chemical reactions under basic condition P—nitro methylbenzene has been taken as the internal standard．Extent of etherbond cleavage has been analyzed quantitatively by high performance liquid chromatographic instrument． Degree ofconversion ofa吲ethers has been determined The results of the experiments show that substituted aryl ethers that containing nitro group(-N02)are easy tO take place nucleophitic substitution in the alkaline medium and then aryl etherbond is cleaved．Extent of etherbond cleavage becomes more and more intensive with higher alkaline concentration,higher reaction temperature，longer reaction time，