Journal of Thermal Analysis and Calorimetry
Volume/Issue:
Volume 77: Issue 2
Chiral resolution by crystallization of host-guest supramolecular complexes
Authors:
A. Grandeury Université de Rouen Unité de Croissance Cristalline et de Modélisation Moléculaire (UC2M2), Sciences et Méthodes Séparatives (SMS), UPRES EA 2659, IRCOF F-76821 Mont Saint-Aignan Cedex France F-76821 Mont Saint-Aignan Cedex France

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L. Renou Université de Rouen Unité de Croissance Cristalline et de Modélisation Moléculaire (UC2M2), Sciences et Méthodes Séparatives (SMS), UPRES EA 2659, IRCOF F-76821 Mont Saint-Aignan Cedex France F-76821 Mont Saint-Aignan Cedex France

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F. Dufour Rexim company Degussa group F-80400 Ham France F-80400 Ham France

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S. Petit Université de Rouen Unité de Croissance Cristalline et de Modélisation Moléculaire (UC2M2), Sciences et Méthodes Séparatives (SMS), UPRES EA 2659, IRCOF F-76821 Mont Saint-Aignan Cedex France F-76821 Mont Saint-Aignan Cedex France

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G. Gouhier Université de Rouen Laboratoire des Fonctions Azotées et Oxygénées Complexes, UMR 6014, IRCOF F-76821 Mont Saint-Aignan Cedex France F-76821 Mont Saint-Aignan Cedex France

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G. Coquerel Université de Rouen Unité de Croissance Cristalline et de Modélisation Moléculaire (UC2M2), Sciences et Méthodes Séparatives (SMS), UPRES EA 2659, IRCOF F-76821 Mont Saint-Aignan Cedex France F-76821 Mont Saint-Aignan Cedex France

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Pages:
377–390
Online Publication Date:
14 Jan 2005
Publication Date:
01 Aug 2004
Article Category:
Research Article
DOI:
https://doi.org/10.1023/b:jtan.0000038979.32555.58
Keywords:
solubility; crystal structure; solid solution; chiral recognition mechanism; enantioseparation; host-guest inclusion; permethylacted cyclodextrin
Restricted access

Abstract  

The crystallization behaviour and the physical characterization of supramolecular complexes formed between permethylated-α-cyclodextrin (TMα-CD) and the enantiomers of phenylethanol (PE) are investigated. According to crystal structure analyses, complexes containing the pure guest enantiomers are almost isomorphous, indicating that the host presents a poor ability to distinguish PE enantiomers at a molecular level. Nevertheless, crystallizations from racemic PE in water induce an efficient chiral discrimination and allow the enantio-separation of the guests despite the existence of a solid solution revealed by XRPD and coupled TG-DSC analyses. The enantiodifferentiation is explained by solubility differences between the two diastereomeric complexes in the studied temperature range. Moreover, it is shown that the diastereomeric complex TMα-CD/(S)-PE crystallizes in two distinct phases: a monohydrate and an anhydrous form, with a transition temperature close to 37C. The insertion of a water molecule in the crystals grown below 37C does not involve any other change of the crystal packing nor of the molecular conformation, but leads to different crystal growth mechanisms inducing different morphologies and distinct thermal behaviours.

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Cover Journal of Thermal Analysis and Calorimetry
Journal of Thermal Analysis and Calorimetry
Print ISSN:
1388-6150
Online ISSN:
1572-8943

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Journal of Thermal Analysis and Calorimetry
Language English
Size A4
Year of
Foundation		 1969
Volumes
per Year		 1
Issues
per Year		 24
Founder Akadémiai Kiadó
Founder's
Address		 H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address		 H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11.
Responsible
Publisher		 Chief Executive Officer, Akadémiai Kiadó
ISSN 1388-6150 (Print)
ISSN 1588-2926 (Online)

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