| 1,1'-联萘-8,8'-二酚的结构和消旋机理的密度泛函研究 |
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| 作者单位： | 中国科学技术大学化学物理系,合肥,230026;淮南帅范学院生物化学系,淮南,232001;中国科学技术大学化学物理系,合肥,230026 |
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| 摘 要： | ![]()
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| 关 键 词： | 密度泛函理论 1 1’-联萘-8 8’-二酚 消旋反应 |
DFT Study on the Structure and Racemization Mechanism of 1,1'-Binaphthalene-8,8'-diol |
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| Liang-guo Da,Tong-tong Lu,Mei Xiang,Tian-jing He,Dong-ming Chen. DFT Study on the Structure and Racemization Mechanism of 1,1'-Binaphthalene-8,8'-diol[J]. Chinese Journal of Chemical Physics, 2008, 21(4): 367-375. DOI: 10.1088/1674-0068/21/04/367-375 |
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| Authors: | Liang-guo Da Tong-tong Lu Mei Xiang Tian-jing He Dong-ming Chen |
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| Abstract: | ![]()
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-C10 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. |
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| Keywords: | Density functional theory (DFT) 1 1'-Binaphthalene-8 8'-diol Racemization |
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