Vitamin E models. Shortened sidechain models of alpha, beta, gamma and delta tocopherol and tocotrienol - a density functional study
Model compounds of alpha-, beta-, gamma-, and delta-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...
Elmentve itt :
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| Dokumentumtípus: | Cikk |
| Megjelent: |
2003
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| Sorozat: | JOURNAL OF MOLECULAR STRUCTURE: THEOCHEM
637 No. 1-3 |
| Tárgyszavak: | |
| doi: | 10.1016/S0166-1280(02)00597-3 |
| mtmt: | 1132566 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/28640 |
| Tartalmi kivonat: | Model compounds of alpha-, beta-, gamma-, and delta-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 oriho-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. (C) 2003 Published by Elsevier B.V. |
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| Terjedelem/Fizikai jellemzők: | 11-26 |
| ISSN: | 0166-1280 |