Enantiomerization Kinetics of 2,2′-Disubstituted Biphenyls: A Dynamic Chiral HPLC Investigation

详细信息    查看全文

• 作者：Max Moskowitz ; Hanhui Xu and Christian Wolf
• 刊名：Israel Journal of Chemistry
• 出版年：2016
• 出版时间：November 2016
• 年：2016
• 卷：56
• 期：11-12
• 页码：1052-1056
• 全文大小：758K
• ISSN：1869-5868

文摘

The enantiomers of eight axially chiral biaryls were separated by chiral HPLC. On-column enantiomerization of 1-(o-tolyl)naphthalene and 2-cyclohexyl-2′-dimethylaminobiphenyl was observed between 10 °C and 35 °C, generating characteristic HPLC elution profiles with a plateau between the resolved enantiomer peaks. Computer simulation of the experimentally obtained chromatograms allowed determination of the Gibbs free energies of activation, ΔG^≠, as 93.2 kJ/mol and 88.4 kJ/mol, respectively.