Optimizing the lifetimes of phenoxonium cations derived from vitamin e via structural modifications

Yanni Yue; Maria L. Novianti; Malcolm E. Tessensohn; Hajime Hirao; Richard D. Webster

doi:10.1039/c5ob01868d

Optimizing the lifetimes of phenoxonium cations derived from vitamin e via structural modifications

Yanni Yue, Maria L. Novianti, Malcolm E. Tessensohn, Hajime Hirao, Richard D. Webster^*

^*Corresponding author for this work

Nanyang Technological University

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

9 Citations (Scopus)

Abstract

Systematic synthesis of a number of new phenolic compounds with structures similar to vitamin E led to the identification of several sterically hindered compounds that when electrochemically oxidised in acetonitrile in a -2e^-/-H⁺ process formed phenoxonium diamagnetic cations that were resistant to hydrolysis reactions. The reactivity of the phenoxonium ions was ascertained by performing cyclic voltammetric scans during the addition of carefully controlled quantities of water into acetonitrile solutions, with the data modelled using digital simulation techniques.

Original language	English
Pages (from-to)	11732-11739
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	48
DOIs	https://doi.org/10.1039/c5ob01868d
Publication status	Published - Oct 13 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Systematic synthesis of a number of new phenolic compounds with structures similar to vitamin E led to the identification of several sterically hindered compounds that when electrochemically oxidised in acetonitrile in a -2e-/-H+ process formed phenoxonium diamagnetic cations that were resistant to hydrolysis reactions. The reactivity of the phenoxonium ions was ascertained by performing cyclic voltammetric scans during the addition of carefully controlled quantities of water into acetonitrile solutions, with the data modelled using digital simulation techniques.",

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AU - Novianti, Maria L.

AU - Tessensohn, Malcolm E.

AU - Hirao, Hajime

AU - Webster, Richard D.

PY - 2015/10/13

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AB - Systematic synthesis of a number of new phenolic compounds with structures similar to vitamin E led to the identification of several sterically hindered compounds that when electrochemically oxidised in acetonitrile in a -2e-/-H+ process formed phenoxonium diamagnetic cations that were resistant to hydrolysis reactions. The reactivity of the phenoxonium ions was ascertained by performing cyclic voltammetric scans during the addition of carefully controlled quantities of water into acetonitrile solutions, with the data modelled using digital simulation techniques.

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Optimizing the lifetimes of phenoxonium cations derived from vitamin e via structural modifications

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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