Separation of non-racemic mixtures of enantiomers: An essential part of optical resolution

F. Faigl, E. Fogassy, Mihály Nógrádi, Emese Pálovics, J. Schindler

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Non-racemic enantiomeric mixtures form homochiral and heterochiral aggregates in melt or suspension, during adsorption or recrystallization, and these diastereomeric associations determine the distribution of the enantiomers between the solid and other (liquid or vapour) phases. That distribution depends on the stability order of the homo- and heterochiral aggregates (conglomerate or racemate formation). Therefore, there is a correlation between the binary melting point phase diagrams and the experimental eeIvs. ee 0 curves (eeI refers to the crystallized enantiomeric mixtures, ee0 is the composition of the starting ones). Accordingly, distribution of the enantiomeric mixtures between two phases is characteristic and usually significant enrichment can be achieved. There are two exceptions: no enrichment could be observed under thermodynamically controlled conditions when the starting enantiomer composition corresponded to the eutectic composition, or when the method used was unsuitable for separation. In several cases, when kinetic control governed the crystallization, the character of the ee 0-eeI curve did not correlate with the melting point binary phase diagram.

Original languageEnglish
Pages (from-to)947-959
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number5
DOIs
Publication statusPublished - 2010

Fingerprint

Enantiomers
enantiomers
Freezing
Phase diagrams
melting points
Melting point
Crystallization
Chemical analysis
phase diagrams
Adsorption
Suspensions
curves
eutectics
Eutectics
liquid phases
Vapors
crystallization
vapor phases
Kinetics
adsorption

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Separation of non-racemic mixtures of enantiomers : An essential part of optical resolution. / Faigl, F.; Fogassy, E.; Nógrádi, Mihály; Pálovics, Emese; Schindler, J.

In: Organic and Biomolecular Chemistry, Vol. 8, No. 5, 2010, p. 947-959.

Research output: Contribution to journalArticle

@article{930670f681804bc4b8e28fb29c7f0a83,
title = "Separation of non-racemic mixtures of enantiomers: An essential part of optical resolution",
abstract = "Non-racemic enantiomeric mixtures form homochiral and heterochiral aggregates in melt or suspension, during adsorption or recrystallization, and these diastereomeric associations determine the distribution of the enantiomers between the solid and other (liquid or vapour) phases. That distribution depends on the stability order of the homo- and heterochiral aggregates (conglomerate or racemate formation). Therefore, there is a correlation between the binary melting point phase diagrams and the experimental eeIvs. ee 0 curves (eeI refers to the crystallized enantiomeric mixtures, ee0 is the composition of the starting ones). Accordingly, distribution of the enantiomeric mixtures between two phases is characteristic and usually significant enrichment can be achieved. There are two exceptions: no enrichment could be observed under thermodynamically controlled conditions when the starting enantiomer composition corresponded to the eutectic composition, or when the method used was unsuitable for separation. In several cases, when kinetic control governed the crystallization, the character of the ee 0-eeI curve did not correlate with the melting point binary phase diagram.",
author = "F. Faigl and E. Fogassy and Mih{\'a}ly N{\'o}gr{\'a}di and Emese P{\'a}lovics and J. Schindler",
year = "2010",
doi = "10.1039/b917564d",
language = "English",
volume = "8",
pages = "947--959",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "5",

}

TY - JOUR

T1 - Separation of non-racemic mixtures of enantiomers

T2 - An essential part of optical resolution

AU - Faigl, F.

AU - Fogassy, E.

AU - Nógrádi, Mihály

AU - Pálovics, Emese

AU - Schindler, J.

PY - 2010

Y1 - 2010

N2 - Non-racemic enantiomeric mixtures form homochiral and heterochiral aggregates in melt or suspension, during adsorption or recrystallization, and these diastereomeric associations determine the distribution of the enantiomers between the solid and other (liquid or vapour) phases. That distribution depends on the stability order of the homo- and heterochiral aggregates (conglomerate or racemate formation). Therefore, there is a correlation between the binary melting point phase diagrams and the experimental eeIvs. ee 0 curves (eeI refers to the crystallized enantiomeric mixtures, ee0 is the composition of the starting ones). Accordingly, distribution of the enantiomeric mixtures between two phases is characteristic and usually significant enrichment can be achieved. There are two exceptions: no enrichment could be observed under thermodynamically controlled conditions when the starting enantiomer composition corresponded to the eutectic composition, or when the method used was unsuitable for separation. In several cases, when kinetic control governed the crystallization, the character of the ee 0-eeI curve did not correlate with the melting point binary phase diagram.

AB - Non-racemic enantiomeric mixtures form homochiral and heterochiral aggregates in melt or suspension, during adsorption or recrystallization, and these diastereomeric associations determine the distribution of the enantiomers between the solid and other (liquid or vapour) phases. That distribution depends on the stability order of the homo- and heterochiral aggregates (conglomerate or racemate formation). Therefore, there is a correlation between the binary melting point phase diagrams and the experimental eeIvs. ee 0 curves (eeI refers to the crystallized enantiomeric mixtures, ee0 is the composition of the starting ones). Accordingly, distribution of the enantiomeric mixtures between two phases is characteristic and usually significant enrichment can be achieved. There are two exceptions: no enrichment could be observed under thermodynamically controlled conditions when the starting enantiomer composition corresponded to the eutectic composition, or when the method used was unsuitable for separation. In several cases, when kinetic control governed the crystallization, the character of the ee 0-eeI curve did not correlate with the melting point binary phase diagram.

UR - http://www.scopus.com/inward/record.url?scp=77149122400&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77149122400&partnerID=8YFLogxK

U2 - 10.1039/b917564d

DO - 10.1039/b917564d

M3 - Article

C2 - 20165781

AN - SCOPUS:77149122400

VL - 8

SP - 947

EP - 959

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 5

ER -