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OALib Journal期刊
ISSN: 2333-9721
费用：99美元
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对位-二取代氮苄叉苯胺还原电位的取代基效应有机化学
DOI: 10.6023/cjoc201411037, PP. 1302-1309
Keywords: 取代氮苄叉苯胺,还原电位,取代基效应,激发态取代基参数,化学位移
Abstract:
合成52种4,4'-二取代氮苄叉苯胺衍生物p-XPhCH=NC6H4Y-p作为模型化合物,系统地研究了取代基效应对其还原电位ERed的影响规律.通过研究表明该类化合物的ERed与桥连键C=N的13CNMR化学位移δC(C=N)没有线性关系,ERed和δC(C=N)两者的影响因素有较大差别,仅用Hammett取代基常数不能很好地表达ERed的变化规律.影响ERed的主要因素有:取代基X的场/诱导效应、取代基X和Y的共轭效应,此外取代基X的激发态取代基参数也有重要影响.上述4个参数与52种化合物的ERed有良好的相关性,相关系数为0.9756,标准偏差为0.052V.在这4个影响因素中,基团X的场/诱导效应、共轭效应和激发态取代基效应对ERed改变的贡献都比较大,而基团Y的共轭效应对还原电位ERed改变的贡献相对较小,但不能忽略它.
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