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Solid Phase Behavior in the Chiral Systems of Various 2-Hydroxy-2-phenylacetic Acid (Mandelic Acid) Derivatives

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Chem. Eng. Data 2015, 60, 3, 721-728
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    Solid Phase Behavior in the Chiral Systems of Various 2-Hydroxy-2-phenylacetic Acid (Mandelic Acid) Derivatives
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    † Institute of Chemistry, University of Rostock, Albert-Einstein-Strasse 3A, 18059 Rostock, Germany
    ‡ Max Planck Institute for Dynamics of Complex Technical Systems, Sandtorstrasse 1, 39106 Magdeburg, Germany
    § Chemical Process Engineering, Otto von Guericke University Magdeburg, Universitätsplatz 2, 39106 Magdeburg, Germany
    *(Synthesis related) Phone: +49-3814986456. Fax: +49-3814986452. E-mail: [email protected]
    *(Solid phase behavior related) Phone: +49-3916110293. Fax: +49-3916110524. E-mail: [email protected]
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    Journal of Chemical & Engineering Data

    Cite this: J. Chem. Eng. Data 2015, 60, 3, 721–728
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    https://doi.org/10.1021/je500845d
    Published January 23, 2015
    Copyright © 2015 American Chemical Society
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    Abstract

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    The solid phase behavior of a series of monosubstituted F-, Cl-, Br-, I-, and CH3- and two 2,4-halogen-disubstituted 2-hydroxy-2-phenylacetic acid (mandelic acid) derivatives was investigated. The study includes detailed information about melting temperature, melting enthalpy, X-ray diffraction data, as well as selected binary phase diagrams of the respective chiral systems. Aside from the known metastable conglomerate 2-chloromandelic acid, evidence for two more metastable conglomerates was found.

    Copyright © 2015 American Chemical Society

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    Supporting Information

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    A summary of XRPD-results for all investigated mandelic acid derivatives, exemplary DSC curves, NMR and HPLC results are provided. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cited By

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    This article is cited by 7 publications.

    1. Rebecca K. Hylton, Graham J. Tizzard, Terence L. Threlfall, Amy L. Ellis, Simon J. Coles, Colin C. Seaton, Eric Schulze, Heike Lorenz, Andreas Seidel-Morgenstern, Matthias Stein, and Sarah L. Price . Are the Crystal Structures of Enantiopure and Racemic Mandelic Acids Determined by Kinetics or Thermodynamics?. Journal of the American Chemical Society 2015, 137 (34) , 11095-11104. https://doi.org/10.1021/jacs.5b05938
    2. Márton Kőrösi, Csaba Varga, Péter Tóth, Noémi Buczkó, Erzsébet Varga, Edit Székely. Experimental Determination of a Chiral Ternary Solubility Diagram and Its Interpretation in Gas Antisolvent Fractionation. Molecules 2023, 28 (5) , 2115. https://doi.org/10.3390/molecules28052115
    3. Laura Bereczki, Amit Zodge, Márton Kőrösi, Tamás Holczbauer, Sourav De, Edit Székely, Petra Bombicz. A bug in enantiomer separation: double salt formation – diastereomeric and double salt structures of 1-cyclohexylethylammonium 2- and 4-chloromandelate. CrystEngComm 2021, 23 (31) , 5367-5376. https://doi.org/10.1039/D1CE00145K
    4. Márton Kőrösi, János Béri, Alina Hanu, Sabine Kareth, Edit Székely. High-pressure melting equilibrium of chiral compounds: A practical study on chlorinated mandelic acids under carbon dioxide atmosphere. Journal of CO2 Utilization 2020, 37 , 173-179. https://doi.org/10.1016/j.jcou.2019.11.026
    5. Heike Lorenz, Erik Temmel, Andreas Seidel-Morgenstern. Continuous Enantioselective Crystallization of Chiral Compounds. 2020, 422-468. https://doi.org/10.1039/9781788013581-00422
    6. Márton Kőrösi, János Madarász, Tamás Sohajda, Edit Székely. A fast, new method to enhance the enantiomeric purity of non-racemic mixtures: self-disproportionation of enantiomers in the gas antisolvent fractionation of chlorine-substituted mandelic acid derivatives. Tetrahedron: Asymmetry 2017, 28 (11) , 1568-1572. https://doi.org/10.1016/j.tetasy.2017.09.005
    7. Huan Guo, Jing Li, Delong Liu, Wanbin Zhang. The Synthesis of Chiral α‐Aryl α‐Hydroxy Carboxylic Acids via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation. Advanced Synthesis & Catalysis 2017, 359 (20) , 3665-3673. https://doi.org/10.1002/adsc.201700846
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    Journal of Chemical & Engineering Data

    Cite this: J. Chem. Eng. Data 2015, 60, 3, 721–728
    Click to copy citationCitation copied!
    https://doi.org/10.1021/je500845d
    Published January 23, 2015
    Copyright © 2015 American Chemical Society
    Request reuse permissions

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