Ab initio and DFT conformational analysis of selected flavones: 5,7-dihydroxyflavone (chrysin) and 7,8-dihydroxyflavone Academic Article uri icon

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  • 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.Key words: flavonoid, flavone, chrysin, ab initio conformational analysis, anti-oxidant, free radical, 5,7-dihydroxy flavone, 7,8-dihydroxyflavone.


  • Lau, Ken S
  • Mantas, Athena
  • Chass, Gregory
  • Ferretti, Fernando H
  • Estrada, Mario
  • Zamarbide, Graziela
  • Csizmadia, Imre G

publication date

  • July 1, 2002