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Solvent effects on the redox properties of thioethers
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Nuclear Chemistry.ORCID iD: 0000-0003-0663-0751
2006 (English)In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 110, no 30, 9513-9517 p.Article in journal (Refereed) Published
Abstract [en]

The one-electron reduction potential of the radical cations of thioanisole (1), benzyl methyl sulfide (2) and 2-hydroxyethyl benzyl sulfide (3) in water, formamide, acetonitrile, acetone, 1,1,1,3,3,3-hexafluoropropan-2-ol, methanol and 2-propanol was investigated by cyclic voltammetry. For comparison the one-electron reduction potentials in water were also measured using pulse radiolysis. The redox potential is strongly influenced by the nature of the solvent and the solvent sensitivity increases with charge localization. The present results have been used to evaluate solvent effects in view of the Kamlet-Taft relationship. The Kamlet-Taft expression quantitatively describes the solvent effects on the redox properties of 1-3 and gives the relative importance of the different solvent properties. The dominating contribution to the solvent effects is the solvent dipolarity/polarizability pi*, whereas alpha appears to be of minor importance. Furthermore, the relationship between the pi* and reduction potential of radical cations of 1-3 appear to be linear. It was also possible to find the same trend between the solvent dipole moment and peak potential of 1-3. These facts indicate that the nature of solvation is mainly nonspecific.

Place, publisher, year, edition, pages
2006. Vol. 110, no 30, 9513-9517 p.
Keyword [en]
one-electron oxidation, aqueous-solution, protein pharmaceuticals, methionine oxidation, alzheimers-disease, hydroxyl radicals, rate constants, peptides, sulfur, oxygen
URN: urn:nbn:se:kth:diva-15871DOI: 10.1021/jp0623746ISI: 000239311100028ScopusID: 2-s2.0-33748307497OAI: diva2:333913
QC 20100525Available from: 2010-08-05 Created: 2010-08-05Bibliographically approved

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