Synthesis and structures of three isoxazole containing Schiff bases

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

doi:10.1107/S2053229620010530

Synthesis and structures of three isoxazole containing Schiff bases

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

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (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 language	English
Pages (from-to)	927-931
Number of pages	20
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	76
Issue number	9
DOIs	https://doi.org/10.1107/S2053229620010530
Publication status	Published - 29 Aug 2020

Keywords

Schiff base
chromism
isoxazole
phenol
crystal structure
hydrogen bonding

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title = "Synthesis and structures of three isoxazole containing Schiff bases",

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.",

keywords = "Schiff base, chromism, isoxazole, phenol, crystal structure, hydrogen bonding",

author = "Mason, {Helen E.} and Howard, {Judith A.K.} and Sparkes, {Hazel A}",

year = "2020",

month = aug,

day = "29",

doi = "10.1107/S2053229620010530",

language = "English",

volume = "76",

pages = "927--931",

journal = "Acta Crystallographica Section C: Crystal Structure Communications",

issn = "0108-2701",

publisher = "Munksgaard International Publishers",

number = "9",

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TY - JOUR

T1 - Synthesis and structures of three isoxazole containing Schiff bases

AU - Mason, Helen E.

AU - Howard, Judith A.K.

AU - Sparkes, Hazel A

PY - 2020/8/29

Y1 - 2020/8/29

N2 - 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.

AB - 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.

KW - Schiff base

KW - chromism

KW - isoxazole

KW - phenol

KW - crystal structure

KW - hydrogen bonding

U2 - 10.1107/S2053229620010530

DO - 10.1107/S2053229620010530

M3 - Article (Academic Journal)

C2 - 32887865

SN - 0108-2701

VL - 76

SP - 927

EP - 931

JO - Acta Crystallographica Section C: Crystal Structure Communications

JF - Acta Crystallographica Section C: Crystal Structure Communications

IS - 9

ER -

Synthesis and structures of three isoxazole containing Schiff bases

Abstract

Keywords

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