Design principles for α-tocopherol analogues

David Shanks; Håkan Frisell; Henrik Ottosson; Lars Engman

doi:10.1039/B515712A

Design principles for α-tocopherol analogues

David Shanks,*^a Håkan Frisell,^b Henrik Ottosson^a and Lars Engman*^a

* Corresponding authors

^a Department of Chemistry, Organic Chemistry, Box 599, Uppsala University, Uppsala, Sweden
E-mail: lars.engman@kemi.uu.se

^b Department of Organic Chemistry, Karlstad University, Karlstad, Sweden

Abstract

An (RO)B3LYP/LANL2DZdp//B3LYP/LANL2DZ model for the prediction of the homolytic bond dissociation enthalpy (BDE) and adiabatic ionisation potential (IP) of phenolic antioxidants containing heavy chalcogens has been developed. The model has been used to probe the relationship between geometry, chalcogen substitution and activity for a series of α-tocopherol analogues of varying ring size. From this, a series of design principles for cyclic antioxidants has emerged, embodied by the compound 4-hydroxy-2,2,3,5,6-pentamethylbenzoselenete (4c). This compound is predicted to have a BDE comparable to α-tocopherol, and should act in a dual chain-breaking and hydroperoxide-decomposing manner, by analogy with other selenide antioxidants. The stability of chalcogen-substituted benzoxetes was considered, and the as yet unsynthesised benzotelluretes are predicted to be stable. Finally, an attempt was made to determine antioxidant mechanism by considering calculated BDE and IP data together with experimental rate data.

Supplementary files

Publication details

The article was received on 04 Nov 2005, accepted on 13 Dec 2005 and first published on 18 Jan 2006

Article type: Paper

DOI: 10.1039/B515712A

Citation: Org. Biomol. Chem., 2006,4, 846-852

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Design principles for α-tocopherol analogues

D. Shanks, H. Frisell, H. Ottosson and L. Engman, Org. Biomol. Chem., 2006, 4, 846
DOI: 10.1039/B515712A
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Organic & Biomolecular Chemistry

Design principles for α-tocopherol analogues

Abstract

Supplementary files

Publication details

Design principles for α-tocopherol analogues

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