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Case of Charge-Assisted Hydrogen Bonding in the Crystal Structure of Sodium Laurate, Lauric Acid

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Abstract

Crystals of Sodium Laurate, Lauric Acid (NaLLA) were obtained and the structure was determined by single-crystal X-ray diffraction. The new crystal form is monoclinic of space group P21/c. The asymmetric unit contains two independent laurate molecules whose carboxylic/carboxylate groups are linked by a low barrier O-H…O hydrogen bond. Two lauric/laurate molecules are in a head-to-head configuration and the elongated hydrophobic chains are parallel to the long b axis. The carboxylic hydrogen atom was found to be disordered, bound on each of the two carboxylate groups in an unsymmetrical way. The non-symmetrical character of the hydrogen bond is related to the presence of two independent fatty acid molecules in the asymmetric unit and is in accordance with the different lengths of the four C-O bonds present in the molecular structure. The crystal structure was analyzed in terms of interactions on the Hirshfeld surface. The packing is stabilized by hydrogen bonds and O…Na ionic interactions in the hydrophilic layer and by C-H…H-C contacts in the hydrophobic layers which are the most enriched major contacts.

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Data Availability

The CIF file and hkl reflections dataset generated and analysed during the current study are available at the Cambridge Structural Database repository (Deposition Number 2,143,409), [https://www.ccdc.cam.ac.uk/]

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Acknowledgements

The PMD2 X-ray diffraction facility (http://crm2.univ-lorraine.fr/lab/fr/services/pmd2x) of the Institut Jean Barriol, Université de Lorraine is acknowledged for the X-ray diffraction measurements, data processing and analysis, and for providing reports for publication.

I.G. thanks the Government of Senegal for scholarships and the support of Nancy ROTARY Club.

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Authors and Affiliations

  1. Université de Lorraine, CNRS, CRM2, F-54000, Nancy, France

    Ibrahima Goudiaby, Benoît Guillot, Emmanuel Wenger & Christian Jelsch

  2. Groupe Matériaux Inorganiques : Chimie Douce et Cristallographie, LCPM, Assane SECK University of Ziguinchor, Ziguinchor, Senegal

    Ibrahima Goudiaby, Magatte Camara & Abdoulaye Gassama

  3. Laboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, Université de Carthage, 7021, Zarzouna, Tunisia

    Sarra Soudani & Cherif ben Nasr

Authors
  1. Ibrahima Goudiaby
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  2. Benoît Guillot
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  3. Emmanuel Wenger
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Correspondence to Christian Jelsch.

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Goudiaby, I., Guillot, B., Wenger, E. et al. Case of Charge-Assisted Hydrogen Bonding in the Crystal Structure of Sodium Laurate, Lauric Acid. J Chem Crystallogr 53, 93–104 (2023). https://doi.org/10.1007/s10870-022-00946-0

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  • DOI: https://doi.org/10.1007/s10870-022-00946-0

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