Eur. Phys. J. D 20, 609-618 (2002)
https://doi.org/10.1140/epjd/e2002-00163-6

Vitamin E models

The effect of heteroatom substitution in 2-ethyl-2-methyl chroman and 2-ethyl-2-methyl-6-hydroxychroman

¹ Global Institute of Computational Molecular and Materials Science VELOCET, 210 Dundas Street W., Suite 810, Toronto, Ontario, Canada M5G 2E8
² Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, Canada M5S 3H6
³ Department of Pharmacology and Pharmacotherapy, Szeged University, Domter12, Szeged, Hungary-6701
⁴ Division of Cardiovascular Pharmacology, Hungarian Academy of Sciences and Szeged University, Domter12, Szeged, Hungary-6701

Corresponding authors: ^a dsetiadi@fixy.org - ^b gchass@fixy.org - ^c pyro@phcol.szote.u-szeged.hu - ^d varro@phcol.szote.u-szeged.hu - ^e papp@phcol.szote.u-szeged.hu - ^f icsizmad@alchemy.chem.utoronto.ca

Received: 9 May 2002
Revised: 9 July 2002
Published online: 13 September 2002

Abstract

The molecular conformations of shortened molecular models of vitamin E (tocopherol and tocotrienol) and their sulfur and selenium congeners were studied computationally at the DFT level of theory [B3LYP/6-31G(d)]. The sequence of stabilization by the various heteroatoms was found to be the following: On the basis of the present structural results it seems that the seleno-congener of vitamin E is a distinct possibility.