Comparison of the structural motifs of acetoacetanilides and related azo pigments

G. Chisholm, A.R. Kennedy, S. Wilson, S.J. Teat

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6 Citations (Scopus)

Abstract

The structures of three methyl-substituted acetoacetanilides and of an azo pigment derived from one of them are presented and discussed together with a review of related known crystal structures. By considering the position of any aromatic substituents it is possible to predict whether the simple acetoacetanilides adopt planar structures with intramolecular hydrogen bonding or twisted structures featuring intermolecular hydrogen bonding. However, we find that the same crystal engineering rules cannot be applied to the related azo pigments: this is apparently due to the presence of an sp2 atom which facilitates the adoption of planar conformations. The thermal properties of the acetoacetanilides were measured by DSC and are discussed with reference to their crystal structures.
Original languageEnglish
Pages (from-to)1046-1053
Number of pages7
JournalActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials
Volume56
Issue number6
DOIs
Publication statusPublished - Dec 2000

Keywords

  • three methyl-substituted acetoacetanilides
  • azo pigment
  • crystal structures
  • aromatic substituents
  • acetoacetanilides
  • hydrogen bonding

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