Long-lived radical cations as model compounds for the reactive one-electron oxidation product of vitamin E

Hong Mei Peng; Becky F. Choules; Wei Wei Yao; Zhengyang Zhang; Richard D. Webster; Peter M.W. Gill

doi:10.1021/jp804135e

Long-lived radical cations as model compounds for the reactive one-electron oxidation product of vitamin E

Hong Mei Peng, Becky F. Choules, Wei Wei Yao, Zhengyang Zhang, Richard D. Webster, Peter M.W. Gill

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Heterocyclic compounds with structures similar to vitamin E, but without the hydroxyl hydrogen atom, were synthesized and their electrochemical behavior examined in acetonitrile solutions and as solids in aqueous solutions of varying pH by attaching the compounds to the surface of a glassy carbon electrode. Compound 1, containing a fully methylated aromatic ring was found to be the most long-lived following one-electron oxidation, with its radical cation (1 ^+.) surviving in acidic aqueous solutions and able to be isolated as a salt, 1^+.(SbF₆^-), when reacted with NOSbF₆ in CH₃CN. Electrochemical, UV-vis and FTIR experiments on 1^+., in addition to the results from theoretical calculations, indicated that the electrochemical, electronic and structural properties of 1^+. are very similar to those of the radical cation of vitamin E.

Original language	English
Pages (from-to)	10367-10374
Number of pages	8
Journal	Journal of Physical Chemistry B
Volume	112
Issue number	33
DOIs	https://doi.org/10.1021/jp804135e
Publication status	Published - Aug 21 2008
Externally published	Yes

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Surfaces, Coatings and Films
Materials Chemistry

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abstract = "Heterocyclic compounds with structures similar to vitamin E, but without the hydroxyl hydrogen atom, were synthesized and their electrochemical behavior examined in acetonitrile solutions and as solids in aqueous solutions of varying pH by attaching the compounds to the surface of a glassy carbon electrode. Compound 1, containing a fully methylated aromatic ring was found to be the most long-lived following one-electron oxidation, with its radical cation (1 +.) surviving in acidic aqueous solutions and able to be isolated as a salt, 1+.(SbF6-), when reacted with NOSbF6 in CH3CN. Electrochemical, UV-vis and FTIR experiments on 1+., in addition to the results from theoretical calculations, indicated that the electrochemical, electronic and structural properties of 1+. are very similar to those of the radical cation of vitamin E.",

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T1 - Long-lived radical cations as model compounds for the reactive one-electron oxidation product of vitamin E

AU - Peng, Hong Mei

AU - Choules, Becky F.

AU - Yao, Wei Wei

AU - Zhang, Zhengyang

AU - Webster, Richard D.

AU - Gill, Peter M.W.

PY - 2008/8/21

Y1 - 2008/8/21

N2 - Heterocyclic compounds with structures similar to vitamin E, but without the hydroxyl hydrogen atom, were synthesized and their electrochemical behavior examined in acetonitrile solutions and as solids in aqueous solutions of varying pH by attaching the compounds to the surface of a glassy carbon electrode. Compound 1, containing a fully methylated aromatic ring was found to be the most long-lived following one-electron oxidation, with its radical cation (1 +.) surviving in acidic aqueous solutions and able to be isolated as a salt, 1+.(SbF6-), when reacted with NOSbF6 in CH3CN. Electrochemical, UV-vis and FTIR experiments on 1+., in addition to the results from theoretical calculations, indicated that the electrochemical, electronic and structural properties of 1+. are very similar to those of the radical cation of vitamin E.

AB - Heterocyclic compounds with structures similar to vitamin E, but without the hydroxyl hydrogen atom, were synthesized and their electrochemical behavior examined in acetonitrile solutions and as solids in aqueous solutions of varying pH by attaching the compounds to the surface of a glassy carbon electrode. Compound 1, containing a fully methylated aromatic ring was found to be the most long-lived following one-electron oxidation, with its radical cation (1 +.) surviving in acidic aqueous solutions and able to be isolated as a salt, 1+.(SbF6-), when reacted with NOSbF6 in CH3CN. Electrochemical, UV-vis and FTIR experiments on 1+., in addition to the results from theoretical calculations, indicated that the electrochemical, electronic and structural properties of 1+. are very similar to those of the radical cation of vitamin E.

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Long-lived radical cations as model compounds for the reactive one-electron oxidation product of vitamin E

Abstract

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