2-氢醌四苯基卟啉的互变异构及其构象分析  

Tautomerism of porphyrinhydroquinone and its conformation

作　　者：陈世清[1] 陈彰评[2] 

机构地区：[1]武汉化工学院化工与制药学院,湖北武汉430073 [2]武汉大学化学与分子科学学院,湖北武汉430072

出　　处：《武汉化工学院学报》2003年第4期19-22,共4页Journal of Wuhan Institute of Chemical Technology

基　　金：国家自然科学基金资助项目(29872033)

摘　　要：直接以氢醌与2硝基5,10,15,20四苯基卟啉及其金属配合物反应,合成了2(2,5二羟基苯基)5,10,15,20四苯基卟啉及其相应的金属配合物 ,同时得到了另一产物 .通过MS、UV、IR、1HNMR及2DNMR测定,确定 与 为互变异构体, 中卟啉环的2取代基由原来的氢醌式异构为半醌式;推测氢醌式取代基存在两个π氢键,从而形成与卟啉环共平面的构象;半醌式取代基只有一个羟基,不能通过π氢键抵消空间位阻的影响,只能采取与卟啉环平面相垂直的构象.2(2,5Dihydroxyphenyl)5,10,15,20tetraphenylporphrin Ⅰ and its tautomer Ⅱ were synthesized by direct reaction of hydroquinone with 2nitro5,10,15,20tetraphenylporphrin.Tautomerism of porphyrinHydroquinone and its conformation were demonstrated by MS,IR,~1 H NMR,2D NMR and UVVis spectra.It turns out that hydroquinone form of the synthetic Ⅰ and semiquinone form of the synthetic Ⅱ are tautomers and that dihedral aogle between 2hydroquinone group and porphyrin ring tend towards 180° and dihedral angle between 2semiquinone group and porphyrin ring tend towards 90°.

关 键 词：氢醌卟啉 互变异构 构象 

分 类 号：O621.143[理学—有机化学]