O,O'-Di-p-toluoyl-(2R,3R)-tartaric acid as supramolecular resolving agent |
| |
Authors: | H Simon K Marthi Gy Pokol E Fogassy D Kozma |
| |
Institution: | (1) Department of Organic Chemical Technology, Budapest University of Technology, Műegyetem rkp. 3, POB 91, 1521, Hungary;(2) Research Group for Technical Analytical Chemistry, Hungarian Academy of Sciences, Budapest University of Technology and Economics Budapest, Szt. Gellért tér 4, 1521, Hungary;(3) Institute of General and Analytical Chemistry, Budapest University of Technology and Economics Budapest, Szt. Gellért tér 4, 1521, Hungary, PO Box 91 |
| |
Abstract: | O,O'-di-p-toluoyl-(2R,3R)-tartaric acid (DPTTA) was investigated as supramolecular complex (SMC) forming resolving agent with three racemic alcohols
(menthol, 4-methyl-2-pentanol, trans-2-iodo-cyclohexanol) by preparative scale experiments and thermoanalytical measurements.
Despite the very small structural difference (two methyl groups) between the O,O'-dibenzoyl-(2R,3R)-tartaric acid (DBTA) and DPTTA, their SMC forming properties with water and racemic alcohols is very different. While DBTA
forms SMC with all the three investigated alcohols, DPTTA forms SMC only with trans-2-iodo-cyclohexanol. DPTTA binds the guest compound less strongly and the stoichiometry of the SMC is also different. The
weaker interactions resulted in less effective optical resolutions. The results of these investigations remind us, that in
optical resolutions during the chiral discrimination process the weaker interactions have a determining role, since DBTA and
DPTTA have the possibility to form the same strong (O-H···O and N-H···O) hydrogen bond network.
This revised version was published online in August 2006 with corrections to the Cover Date. |
| |
Keywords: | enantiomer separation enantioselectivity 3R)-tartaric acid complex formation optical resolution O O'-di-p-toluoyl-(2R |
本文献已被 SpringerLink 等数据库收录! |
|