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Journal of Chemical Crystallography

, Volume 42, Issue 7, pp 752–758 | Cite as

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

  • Mario CetinaEmail author
  • Ante Nagl
  • Dajana Gašo-SokačEmail author
  • Spomenka Kovač
  • Valentina Bušić
  • Dijana Saftić
Original Paper

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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Keywords

Quaternary pyridinium salts Phenacyl bromides Pyridoxal oxime derivatives X-ray diffraction Supramolecular assembling 

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Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Mario Cetina
    • 1
    Email author
  • Ante Nagl
    • 1
  • Dajana Gašo-Sokač
    • 2
    • 3
    Email author
  • Spomenka Kovač
    • 2
    • 3
  • Valentina Bušić
    • 2
  • Dijana Saftić
    • 4
  1. 1.Department of Applied Chemistry, Faculty of Textile TechnologyUniversity of ZagrebZagrebCroatia
  2. 2.Department of ChemistryJ.J. Strossmayer University of OsijekOsijekCroatia
  3. 3.Faculty of Food TechnologyJ.J. Strossmayer University of OsijekOsijekCroatia
  4. 4.Ruđer Bošković InstituteZagrebCroatia

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