Ab initio and DFT conformational analysis of selected flavones

5,7-Dihydroxyflavone (chrysin) and 7,8-dihydroxyflavone

Ken S. Lau, Athena Mantas, Gregory A. Chass, Fernando H. Ferretti, Mario Estrada, Graziela Zamarbide, I. Csizmadia

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Ab initio and DFT conformational analysis was performed on the flavone derivatives chrysin (5,7-dihydroxyflavone; 2-phenyl-5,7-dihydroxy-4H-1-benzopyran-4-one) and 7,8-dihydroxyflavone (2-phenyl-7,8-dihydroxy-4H-1-benzopyran-4-one). The structural features required for optimal stabilization in each molecule were identified. It was discovered that sparsely placed hydroxyl groups, particularly with hydrogen bond-like interactions, resulted in lowering the potential energy minimum for the molecules. It was also noted that one of the factors capable of destroying co-planarity was steric interference between closely placed functional groups across the phenyl and the benzo-γ-pyrane ring. Studies performed on the radical forms of the flavonoids, however, showed that the unpaired electron is confined only to the benzo-γ-pyrane ring, and not delocalized across the phenyl ring.

Original languageEnglish
Pages (from-to)845-855
Number of pages11
JournalCanadian Journal of Chemistry
Volume80
Issue number7
DOIs
Publication statusPublished - 2002

Fingerprint

Flavones
flavone
Discrete Fourier transforms
Flavonoids
Molecules
Potential energy
Hydroxyl Radical
Functional groups
Hydrogen bonds
Stabilization
Derivatives
Electrons
6,7-dihydroxyflavone
chrysin
benzopyran-4-one

Keywords

  • 5,7-dihydroxyflavone
  • 7,8-dihydroxyflavone
  • Ab initio conformational analysis
  • Anti-oxidant
  • Chrysin
  • Flavone
  • Flavonoid
  • Free radical

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Ab initio and DFT conformational analysis of selected flavones : 5,7-Dihydroxyflavone (chrysin) and 7,8-dihydroxyflavone. / Lau, Ken S.; Mantas, Athena; Chass, Gregory A.; Ferretti, Fernando H.; Estrada, Mario; Zamarbide, Graziela; Csizmadia, I.

In: Canadian Journal of Chemistry, Vol. 80, No. 7, 2002, p. 845-855.

Research output: Contribution to journalArticle

Lau, Ken S. ; Mantas, Athena ; Chass, Gregory A. ; Ferretti, Fernando H. ; Estrada, Mario ; Zamarbide, Graziela ; Csizmadia, I. / Ab initio and DFT conformational analysis of selected flavones : 5,7-Dihydroxyflavone (chrysin) and 7,8-dihydroxyflavone. In: Canadian Journal of Chemistry. 2002 ; Vol. 80, No. 7. pp. 845-855.
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