Vitamin E models. Shortened sidechain models of α, β, γ and δ tocopherol and tocotrienol - A density functional study

David H. Setiadi, Gregory A. Chass, Ladislaus L. Torday, Andras Varro, Julius Gy Papp

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15 Citations (Scopus)


Model compounds of α-, β-, γ-, and δ-tocopherol and Tocotrienol, as well as their sulphur and selenium congeners, were subjected to density functional analysis. The mono methyl substitution either stabilized or destabilized the ring structures to a small extent as assessed in terms of isodesmic reactions. In general, multiple methyl substitutions destabilized the ring. Dimethyl para-substitution results in electronic stabilization and steric repulsion being nearly additive. This was not the case for ortho-dimethyl derivatives, whereby steric repulsions dominate; the meta-substituted models reflect the same trend to a lesser degree. Structurally, the phenolic hydroxyl orientation was approximately planar, with the hydroxyl proton oriented away from the adjacent Me group whenever the structure permitted such an orientation.

Original languageEnglish
Pages (from-to)11-26
Number of pages16
JournalJournal of Molecular Structure: THEOCHEM
Issue number1-3
Publication statusPublished - Oct 3 2003



  • Density functional theory
  • Methyl substitution
  • Orientation of phenolic OH
  • Tocopherol
  • Tocotrienol

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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