Solvent effect in NMR enantiomeric analysis using (S)-1,1′-binaphthyl-2,2′-diol as a chiral solvating agent |
| |
Authors: | O V Mikhalev O R Malyshev M G Vinogradov G V Chel'tsova-Bebutova A V Ignatenko |
| |
Institution: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation
|
| |
Abstract: | The determination of the enantiomeric composition of chiral compounds by1H,13C, and31P NMR spectroscopy in the presence of (S)-1,1′-binaphthyl-2,2′-diol demonstrates that the enantioselectivity of the method increases when the polarity of a solvent decreases as follows: CD3OD-D2O (4 ∶ 1) < CD3OD < CDCl3 < CDCl3-CCl4 (1 ∶ 1) < C6D6. The effect is caused by increase in stability of solvating agent-substrate complexes formed through the hydrogen bonds. Pantolactone, esters of substituted cyclopropanecarboxylic acids, amino alcohol propranolol, and 2,2′-bis(diphenylphosphinyl)-1,1′-binaphthyl were used as the substrates. |
| |
Keywords: | |
本文献已被 SpringerLink 等数据库收录! |
|