DFT Study on the Structure and Racemization Mechanism of 1,1 ＇- Bina phthalene-8,8 ＇-diol  

作　　者：Liang-guo Da Tong-tong Lu Mei Xiang Tian-jing He Dong-ming Chen 

机构地区：[1]Department of Chemical Physics, University of Science and Technology of China, Hefei 230025, China [2]Department of Chemical Biology, Huainan Normal University, Huainan 232001, China

出　　处：《Chinese Journal of Chemical Physics》2008年第4期367-375,共9页化学物理学报（英文）

摘　　要：Density functional theory （DFT） was applied to study the ground state geometries and isomerization processes of 1,1＇-binaphthalene-8,8＇-diol. Three isomers, denoted as ISO1, ISO2, and ISO3, were found, distinguished by different orientations of the OH groups, and each OH-orientational isomer has R- and S-enantiomer. The conformational stabilities of these isomers were investigated by tracking the energy change with respect to the ring-to-ring torsion. The inter-conversions between the three OH-orientational S-isomers were found to have quite low barriers owing to the nearly free rotation of OH groups around the O-C single bonds. The S-R enantiomerization of ISO1 and ISO2 can take place through the ring-ring torsion around the C1-C1/ single bond, either in the anti-rotation manner or in the syn-rotation manner. The barriers of the anti routes are lower than those of the corresponding syn routes by 87.95 and 75.04 kJ/mol. For the S-R enantiomerization of ISO3, only the anti route was found. The barriers for the anti route enantiomerizations of ISO1, ISO2, and ISO3 are 119.61, 120.43, and 121.59 kJ/mol, respectively. A parallel reaction mechanism via three anti enantiomerization routes was proposed for the racemization of 1,1＇-binaphthalene-8,8＇-diol.

关 键 词：Density functional theory （DFT） 1 1＇-Binaphthalene-8 8＇-diol RACEMIZATION 

分 类 号：O622.3[理学—有机化学] TQ655[理学—化学]