Anodic oxidation of m-terphenyl thio-, selenoand telluroethers: Lowered oxidation potentials due to chalcogen⋯πinteraction

Malika Ammam; Uzma I. Zakai; George S. Wilson; Richard S. Glass

doi:10.1351/PAC-CON-09-08-10

Anodic oxidation of m-terphenyl thio-, selenoand telluroethers: Lowered oxidation potentials due to chalcogen⋯πinteraction

Malika Ammam, Uzma I. Zakai, George S. Wilson, Richard S. Glass

Chemistry and Biochemistry

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

9 Scopus citations

Abstract

The electrochemistry of m-terphenylthio-, seleno-, and telluroethers was studied using cyclic voltammetry in acetonitrile. All of the compounds studied showed irreversible oxidations. The first oxidation potentials for the thio- and selenoethers are less positive than expected. This facilitation in oxidation is ascribed to through-space S⋯πand Se⋯πinteraction, respectively, on removal of an electron. No evidence for a comparable effect was found for the phenyltelluro-ethers studied.

Original language	English (US)
Pages (from-to)	555-563
Number of pages	9
Journal	Pure and Applied Chemistry
Volume	82
Issue number	3
DOIs	https://doi.org/10.1351/PAC-CON-09-08-10
State	Published - 2010

Keywords

Electrochemistry
Facilitated oxidation; photoelectron spectroscopy
Se⋯π interaction
Substituted m-terphenyls
Sulfur

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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10.1351/PAC-CON-09-08-10

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title = "Anodic oxidation of m-terphenyl thio-, selenoand telluroethers: Lowered oxidation potentials due to chalcogen⋯πinteraction",

abstract = "The electrochemistry of m-terphenylthio-, seleno-, and telluroethers was studied using cyclic voltammetry in acetonitrile. All of the compounds studied showed irreversible oxidations. The first oxidation potentials for the thio- and selenoethers are less positive than expected. This facilitation in oxidation is ascribed to through-space S⋯πand Se⋯πinteraction, respectively, on removal of an electron. No evidence for a comparable effect was found for the phenyltelluro-ethers studied.",

keywords = "Electrochemistry, Facilitated oxidation; photoelectron spectroscopy, Se⋯π interaction, Substituted m-terphenyls, Sulfur",

author = "Malika Ammam and Zakai, {Uzma I.} and Wilson, {George S.} and Glass, {Richard S.}",

note = "Funding Information: The authors thank the National Science Foundation for financial support of this research (CHE-0455575) and Dr. Nadine E. Gruhn for measuring the PE spectra at the Center for Gas-Phase Electron Spectroscopy, The University of Arizona.",

year = "2010",

doi = "10.1351/PAC-CON-09-08-10",

language = "English (US)",

volume = "82",

pages = "555--563",

journal = "Pure and Applied Chemistry",

issn = "0033-4545",

publisher = "IUPAC Secretariat",

number = "3",

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TY - JOUR

T1 - Anodic oxidation of m-terphenyl thio-, selenoand telluroethers

T2 - Lowered oxidation potentials due to chalcogen⋯πinteraction

AU - Ammam, Malika

AU - Zakai, Uzma I.

AU - Wilson, George S.

AU - Glass, Richard S.

N1 - Funding Information: The authors thank the National Science Foundation for financial support of this research (CHE-0455575) and Dr. Nadine E. Gruhn for measuring the PE spectra at the Center for Gas-Phase Electron Spectroscopy, The University of Arizona.

PY - 2010

Y1 - 2010

N2 - The electrochemistry of m-terphenylthio-, seleno-, and telluroethers was studied using cyclic voltammetry in acetonitrile. All of the compounds studied showed irreversible oxidations. The first oxidation potentials for the thio- and selenoethers are less positive than expected. This facilitation in oxidation is ascribed to through-space S⋯πand Se⋯πinteraction, respectively, on removal of an electron. No evidence for a comparable effect was found for the phenyltelluro-ethers studied.

AB - The electrochemistry of m-terphenylthio-, seleno-, and telluroethers was studied using cyclic voltammetry in acetonitrile. All of the compounds studied showed irreversible oxidations. The first oxidation potentials for the thio- and selenoethers are less positive than expected. This facilitation in oxidation is ascribed to through-space S⋯πand Se⋯πinteraction, respectively, on removal of an electron. No evidence for a comparable effect was found for the phenyltelluro-ethers studied.

KW - Electrochemistry

KW - Facilitated oxidation; photoelectron spectroscopy

KW - Se⋯π interaction

KW - Substituted m-terphenyls

KW - Sulfur

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U2 - 10.1351/PAC-CON-09-08-10

DO - 10.1351/PAC-CON-09-08-10

M3 - Article

AN - SCOPUS:77950145038

VL - 82

SP - 555

EP - 563

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

SN - 0033-4545

IS - 3

ER -

Anodic oxidation of m-terphenyl thio-, selenoand telluroethers: Lowered oxidation potentials due to chalcogen⋯πinteraction

Abstract

Keywords

ASJC Scopus subject areas

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