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O,O'-Di-p-toluoyl-(2R,3R)-tartaric acid as supramolecular resolving agent

O,O'-Di-p-toluoyl-(2R,3R)-tartaric acid as supramolecular resolving agent O,O'-di- p -toluoyl-(2 R ,3 R )-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-(2 R ,3 R )-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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Thermal Analysis and Calorimetry Springer Journals

O,O'-Di-p-toluoyl-(2R,3R)-tartaric acid as supramolecular resolving agent

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References (11)

Publisher
Springer Journals
Copyright
Copyright © 2003 by Kluwer Academic Publisher/Akadémiai Kiadó
Subject
Chemistry; Inorganic Chemistry; Physical Chemistry; Polymer Sciences; Measurement Science, Instrumentation
ISSN
1388-6150
eISSN
1572-8943
DOI
10.1023/A:1026334021007
Publisher site
See Article on Publisher Site

Abstract

O,O'-di- p -toluoyl-(2 R ,3 R )-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-(2 R ,3 R )-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.

Journal

Journal of Thermal Analysis and CalorimetrySpringer Journals

Published: Oct 1, 2003

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