2,2’-二取代联萘化合物的NMR研究

根据~1H NMR,同核自旋去偶和二维COSY(400MHZ)的实验结果,对四种2,2′-二取代-1,1~1-联萘化合物的萘环质了作了归属指定,指出联萘酚的H_8(H’_8)共振峰应在高场,不宜接 Sadtler标准谱图指定在低场。讨论了萘环环电流各向异性和二萘环平面二面角对萘环质子的影响。当萘环二面角变化时,H_8(H’_8)受到的影响最大,随着二面角减小,H_8(H’_8)的共振明显地移向低场。

Proton NMR Study of 2, 2'-Disubstituted-binaphthyl Compounds

The assignment of ~1H NMR spectra of compounds 2,2'-dihydroxy1-1, 1'-binap-hthyl(1), 2, 2'-dimethoxy-1,1'-binaphthyl, 2, 2'-ethylenedioxy-1, 1'-binaphthyland 2,2'-methylenedioxy-1,1'-binaphthyl was made according to the 400 MHz~1H NMR spectra, the homonuclear decoupling and 2D COSY spectra. The resultsshow that the H_8(H_8') resonances are located at up field rather than at downfield for 1. The anisotropic effects of the naphthlene ring and the influence ofthe dihedral angle between two naphthlene rings on the protons of the naphthlenerings were disscussed. It was found that the most sensitive protons are H_3(H_8')while the dihedral angle of two naphthlene rings is changed. As the dihedral an-gle decreases, the resonances of H_8(H_8') move toward down field obviously.