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


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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  1. Somani SM, Romano JA Jr (2001) Chemical warfare agents: toxicity at low levels. CRS Press LLC, Boca Raton

    Google Scholar 

  2. Bajgar J (2004) Adv Clin Chem 38:151–216

    Article  CAS  Google Scholar 

  3. Dohnal V, Kuča K, Jun D (2005) J Appl Biomed 3:139–145

    CAS  Google Scholar 

  4. Kuča K, Bartošová L, Jun D, Patočka J, Cabal J, Kassa J, Kunešová G (2005) Biomed Papers 149:75–82

    Google Scholar 

  5. Kassa J (2002) Clin Toxicol 40:803–816

    Article  CAS  Google Scholar 

  6. Jokanović M, Stojiljković MP (2006) Eur J Pharmacol 553:10–17

    Article  Google Scholar 

  7. Kovarik Z, Čalić M, Šinko G, Bosak A, Berend S, Lucić Vrdoljak A, Radić B (2008) Chem Biol Interact 175:173–179

    Article  CAS  Google Scholar 

  8. Kovarik Z, Čalić M, Bosak A, Šinko G, Jelić D (2008) Croat Chim Acta 81:47–57

    CAS  Google Scholar 

  9. Primožič I, Odžak R, Tomić S, Simeon-Rudolf V, Reiner E (2004) J Med Chem Def 2:1–30

    Google Scholar 

  10. Reiner E, Simeon-Rudolf V (2006) Arh Hig Rada Toksikol 57:171–179

    CAS  Google Scholar 

  11. Milatović D, Vorkapić-Furač J, Škrinjarić-Špoljarić M, Reiner E (1989) Acta Pharm Jugosl 39:281–287

    Google Scholar 

  12. Gašo-Sokač D, Katalinić M, Kovarik Z, Bušić V, Kovač S (2010) Chem Biol Interact 187:234–237

    Article  Google Scholar 

  13. Oxford Diffraction, Xcalibur CCD System. CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England

  14. Sheldrick GM (2008) Acta Crystallogr A64:112–122

    CAS  Google Scholar 

  15. Spek AL (2008) J Appl Crystallogr 36:7–13

    Article  Google Scholar 

  16. Jukić M, Hergold-Brundić A, Cetina M, Nagl A, Vorkapić-Furač J (2003) Struct Chem 14:597–604

    Article  Google Scholar 

  17. Allen FH (2002) Acta Crystallogr B58:380–388

    CAS  Google Scholar 

  18. Bernstein J, Davis RE, Shimoni L, Chang NL (1995) Angew Chem Int Ed Engl 34:1555–1573

    Article  CAS  Google Scholar 

  19. Hunter CA, Sanders JKM (1990) J Am Chem Soc 112:5525–5534

    Article  CAS  Google Scholar 

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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).

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