High-Pressure Crystallization and Thermodynamic Stability Study on the Resolution of High-Density Enantiomers from Low-Density Racemates

[Image: see text] High-pressure recrystallization could be the cheapest clean method of resolving enantiomers from the racemates defying Wallach’s rule. We have investigated the effect of pressure on sodium tartrate monohydrate (NaTa·H(2)O), a notorious exception from Wallach’s rule: both racemic po...

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Autores principales: Roszak, Kinga, Katrusiak, Andrzej
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9841603/
https://www.ncbi.nlm.nih.gov/pubmed/36598359
http://dx.doi.org/10.1021/acs.orglett.2c03747
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author Roszak, Kinga
Katrusiak, Andrzej
author_facet Roszak, Kinga
Katrusiak, Andrzej
author_sort Roszak, Kinga
collection PubMed
description [Image: see text] High-pressure recrystallization could be the cheapest clean method of resolving enantiomers from the racemates defying Wallach’s rule. We have investigated the effect of pressure on sodium tartrate monohydrate (NaTa·H(2)O), a notorious exception from Wallach’s rule: both racemic polymorphs α-dl-NaTa·H(2)O and β-dl-NaTa·H(2)O are less dense than the enantiomers. According to the mobile-equilibrium principle, such high-density enantiomorphs should spontaneously separate under high pressures. The pressure dependence of the Gibbs free energy explains the preferential crystallization of mixed enantiomers of NaTa·H(2)O.
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spelling pubmed-98416032023-01-17 High-Pressure Crystallization and Thermodynamic Stability Study on the Resolution of High-Density Enantiomers from Low-Density Racemates Roszak, Kinga Katrusiak, Andrzej Org Lett [Image: see text] High-pressure recrystallization could be the cheapest clean method of resolving enantiomers from the racemates defying Wallach’s rule. We have investigated the effect of pressure on sodium tartrate monohydrate (NaTa·H(2)O), a notorious exception from Wallach’s rule: both racemic polymorphs α-dl-NaTa·H(2)O and β-dl-NaTa·H(2)O are less dense than the enantiomers. According to the mobile-equilibrium principle, such high-density enantiomorphs should spontaneously separate under high pressures. The pressure dependence of the Gibbs free energy explains the preferential crystallization of mixed enantiomers of NaTa·H(2)O. American Chemical Society 2023-01-04 /pmc/articles/PMC9841603/ /pubmed/36598359 http://dx.doi.org/10.1021/acs.orglett.2c03747 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Roszak, Kinga
Katrusiak, Andrzej
High-Pressure Crystallization and Thermodynamic Stability Study on the Resolution of High-Density Enantiomers from Low-Density Racemates
title High-Pressure Crystallization and Thermodynamic Stability Study on the Resolution of High-Density Enantiomers from Low-Density Racemates
title_full High-Pressure Crystallization and Thermodynamic Stability Study on the Resolution of High-Density Enantiomers from Low-Density Racemates
title_fullStr High-Pressure Crystallization and Thermodynamic Stability Study on the Resolution of High-Density Enantiomers from Low-Density Racemates
title_full_unstemmed High-Pressure Crystallization and Thermodynamic Stability Study on the Resolution of High-Density Enantiomers from Low-Density Racemates
title_short High-Pressure Crystallization and Thermodynamic Stability Study on the Resolution of High-Density Enantiomers from Low-Density Racemates
title_sort high-pressure crystallization and thermodynamic stability study on the resolution of high-density enantiomers from low-density racemates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9841603/
https://www.ncbi.nlm.nih.gov/pubmed/36598359
http://dx.doi.org/10.1021/acs.orglett.2c03747
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