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Synthesis and structures of three isoxazole‐containing Schiff bases
Author(s) -
Mason Helen E.,
Howard Judith A. K.,
Sparkes Hazel A.
Publication year - 2020
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229620010530
Subject(s) - isoxazole , schiff base , chemistry , stereochemistry
The synthesis and structures of three isoxazole‐containing Schiff bases are reported, namely, ( E )‐2‐{[(isoxazol‐3‐yl)imino]methyl}phenol, C 10 H 8 N 2 O 2 , ( E )‐2‐{[(5‐methylisoxazol‐3‐yl)imino]methyl}phenol, C 11 H 10 N 2 O 2 , and ( E )‐2,4‐di‐ tert ‐butyl‐6‐{[(isoxazol‐3‐yl)imino]methyl}phenol, C 18 H 24 N 2 O 2 . 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.