Synthesis and structures of three isoxazole-containing Schiff bases

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

doi:10.1107/s2053229620010530

Synthesis and structures of three isoxazole-containing Schiff bases

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

Authors

Helen E. Mason

Judith A.K. Howard

Hazel A. Sparkes

Abstract

The synthesis and structures of three isoxazole-containing Schiff bases are reported, namely, (E)-2-{[(isoxazol-3-yl)imino]methyl}phenol, C10H8N2O2, (E)-2-{[(5-methylisoxazol-3-yl)imino]methyl}phenol, C11H10N2O2, and (E)-2,4-di-tert-butyl-6-{[(isoxazol-3-yl)imino]methyl}phenol, C18H24N2O2. 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 structures existing in the enol rather than the 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.

Citation

Mason, H. E., Howard, J. A., & Sparkes, H. A. (2020). Synthesis and structures of three isoxazole-containing Schiff bases. Acta Crystallographica Section C: Structural Chemistry, 76(9), 927-931. https://doi.org/10.1107/s2053229620010530

Journal Article Type	Article
Acceptance Date	Jul 31, 2020
Online Publication Date	Aug 29, 2020
Publication Date	2020-09
Deposit Date	Sep 1, 2020
Publicly Available Date	Sep 1, 2020
Journal	Acta Crystallographica Section C: Structural Chemistry
Publisher	International Union of Crystallography
Peer Reviewed	Peer Reviewed
Volume	76
Issue	9
Pages	927-931
DOI	https://doi.org/10.1107/s2053229620010530

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