Synthesis and structures of three isoxazole containing Schiff bases

Helen E. Mason, Judith A.K. Howard, Hazel A Sparkes*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

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Abstract

The synthesis and structures of three isoxazole containing Schiff bases are reported, namely (E)-2-((isoxazol-3-ylimino)methyl)phenol, (E)-2-(((5-methylisoxazol-3-yl)imino)methyl)phenol and (E)-2,4-di-tert-butyl-6-((isoxazol-3-ylimino)methyl)phenol. All three structures contain an intramolecular O-H···N hydrogen bond, alongside weaker intermolecular C-H···N and C-H···O contacts. The C-O(H) and imine C=N bond lengths were consistent with the structures existing in the enol rather than keto form. Despite having dihedral angles < 25° none of the compounds were observed to be strongly thermochromic, unlike their anil counterparts, however all three compounds showed a visible colour change upon irradiation with UV light.
Original languageEnglish
Pages (from-to)927-931
Number of pages20
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume76
Issue number9
DOIs
Publication statusPublished - 29 Aug 2020

Keywords

  • Schiff base
  • chromism
  • isoxazole
  • phenol
  • crystal structure
  • hydrogen bonding

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