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Extensive Intramolecular and Intermolecular Interactions in Two Quaternary Salts of the Pyridoxal Oxime

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Abstract

Two derivatives of pyridoxal oxime (1) were prepared by quaternization of pyridoxal oxime with phenacyl bromide and 2-methoxyphenacyl bromide. The crystal structures of the 1-phenacyl-3-hydroxy-4-hydroxyiminomethyl-5-hydroxymethyl-2-methylpyridinium bromide (2) and the novel 3-hydroxy-4-hydroxyiminomethyl-5-hydroxymethyl-2-methyl-1-(2′-methoxyphenacyl) pyridinium bromide (3) have been determined by X-ray diffraction method. The conformation of these two pyridoxal oxime phenacyl derivatives is locked by numerous intramolecular hydrogen bonds. The O–H···Br, C–H···Br and C–H···O hydrogen bonds in 2 and 3 form complex three-dimensional network. Supramolecular structure of 3 also contains C–H···π and π···π interactions which link neighbouring cations.

Graphical Abstract

In two derivatives of pyridoxal oxime, discrete interplay between intramolecular and intermolecular interactions during the crystallization process influence on the conformation of the molecules

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Authors and Affiliations

  1. Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, 10000, Zagreb, Croatia

    Mario Cetina & Ante Nagl

  2. Department of Chemistry, J.J. Strossmayer University of Osijek, Kuhačeva 20, 31000, Osijek, Croatia

    Dajana Gašo-Sokač, Spomenka Kovač & Valentina Bušić

  3. Faculty of Food Technology, J.J. Strossmayer University of Osijek, Kuhačeva 20, 31000, Osijek, Croatia

    Dajana Gašo-Sokač & Spomenka Kovač

  4. Ruđer Bošković Institute, Bijenička 54, 10000, Zagreb, Croatia

    Dijana Saftić

Authors
  1. Mario Cetina
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  2. Ante Nagl
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  3. Dajana Gašo-Sokač
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  4. Spomenka Kovač
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  5. Valentina Bušić
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  6. Dijana Saftić
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Correspondence to Mario Cetina or Dajana Gašo-Sokač.

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Cetina, M., Nagl, A., Gašo-Sokač, D. et al. Extensive Intramolecular and Intermolecular Interactions in Two Quaternary Salts of the Pyridoxal Oxime. J Chem Crystallogr 42, 752–758 (2012). https://doi.org/10.1007/s10870-012-0312-y

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  • DOI: https://doi.org/10.1007/s10870-012-0312-y

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