Crystallization of chiral compounds: thermodynamical, structural and practical aspects

Бредихин, А. А.; Бредихина, З. А.; Zakharychev, Dmitry V.

doi:10.1016/j.mencom.2012.06.001

Cited by 41 publications

(55 citation statements)

References 109 publications

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“…For instance, the prevalence of racemic compounds (depicted in ca. 90 % of chiral systems) over conglomerates (less than 10 % of occurrences) remains a challenging question . Concerning the infrequently identified enantiomeric solid solutions, the absence of chiral selectivity of the crystallographic sites provides valuable opportunities to investigate molecular mechanisms of chiral discrimination, in particular, if this behaviour can be compared to that of a highly stereoselective racemic compound existing in the same system.…”

Section: Introductionmentioning

confidence: 99%

Prenucleation Self‐Assembly and Chiral Discrimination Mechanisms during Solution Crystallisation of Racemic Diprophylline

Brandel

Cartigny

Coquerel

et al. 2016

Chemistry A European J

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This version is available at https://strathprints.strath.ac.uk/58510/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. FULL PAPER Pre-Nucleation Self-Assembly and Chiral Discrimination Mechanisms during Solution Crystallization of Racemic DiprophyllineClément Brandel,* [a] Yohann Cartigny, [a] Gérard Coquerel, [a] Joop H. ter Horst, [b] and Samuel Petit [a] Abstract: The crystallization behavior of (RS)-Diprophylline (DPL) in two different solvents is investigated in order to assess the incidence of solvated pre-associations on nucleation, crystal growth and chiral discrimination. In the solvated state, Raman spectroscopy shows that dimeric associations similar to those depicted in the crystalline solid solution (ssRII) predominate in isopropyl alcohol (IPA), which may account for the systematic spontaneous nucleation of this crystal form from this solvent. By contrast, spontaneous nucleation in dimethylformamide yields the stable racemic compound RI, consistently with the distinct features of the Raman spectrum collected in this solvent. A crystal growth study of ssRII in IPA reveals that the crystal habitus is impacted by the solution enantiomeric excess which is explained by an increased competition between homo and heterochiral pre-associations. This is supported by a molecular modelling study on the enantiomeric selectivity of the DPL crystal lattices. The combination of assessment methods on solution chemistry, nucleation and chiral discrimination provides methodological tools from which the occurrence of solid solutions can be rationalized.

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Section: Introductionmentioning

confidence: 99%

Prenucleation Self‐Assembly and Chiral Discrimination Mechanisms during Solution Crystallisation of Racemic Diprophylline

Brandel

Cartigny

Coquerel

et al. 2016

Chemistry A European J

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“…[13][14][15] Recently we have shown that timolol maleate 1Á(HO 2 CCH) 2 crystallizes as a solid solution of the pure enantiomer and racemic compound. 16 This type of crystallization does not favor enantiopurification via recrystallization.…”

Section: Contents Lists Available At Sciencedirectmentioning

confidence: 99%

From racemic epichlorohydrin to a single enantiomer of the drug timolol maleate

Бредихина

Fayzullin

Kurenkov

et al. 2015

Tetrahedron: Asymmetry

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“…Firstly, both (S)-9 and rac-9 have very similar melting temperatures, 118-119°C and 117-119°C. Secondly, 3-(4-methoxyphenoxy)-propane-1,2-diol, synthetic precursor of crowns 3, forms an ideal continuous solid solution of enantiomers in full concentration region [19].…”

Section: D-hámentioning

confidence: 99%

Crystallographic evidence of side-arm lariat effect in the series of chiral ortho- and para-methoxyphenoxymethyl-15-crown-5 complexes with sodium perchlorate

Бредихин¹,

Gubaidullin²,

Бредихина³

et al. 2013

Journal of Molecular Structure

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Crystallization of chiral compounds: thermodynamical, structural and practical aspects

Cited by 41 publications

References 109 publications

Prenucleation Self‐Assembly and Chiral Discrimination Mechanisms during Solution Crystallisation of Racemic Diprophylline

Prenucleation Self‐Assembly and Chiral Discrimination Mechanisms during Solution Crystallisation of Racemic Diprophylline

From racemic epichlorohydrin to a single enantiomer of the drug timolol maleate

Crystallographic evidence of side-arm lariat effect in the series of chiral ortho- and para-methoxyphenoxymethyl-15-crown-5 complexes with sodium perchlorate

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