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Redox and acidity properties of 2,2 '- and 4,4 '-biphenol and the corresponding phenoxyl radicals
KTH, Superseded Departments, Chemistry.ORCID iD: 0000-0003-0663-0751
KTH, Superseded Departments, Chemistry.
KTH, Superseded Departments, Chemistry.
2002 (English)In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 106, no 18, 4758-4762 p.Article in journal (Refereed) Published
Abstract [en]

The redox and acidity properties of 2,2'- and 4,4'-biphenol and the corresponding phenoxyl radicals have been determined using UV-vis spectrophotometry, pulse radiolysis, and cyclic voltammetry. The pK(a)'s for 4,4'-HO-Ph-Ph-OH, 4,4'-O--Ph-Ph-OH, 4,4'-O-circle-Ph-Ph-OH, 2,2'-HO-Ph-Ph-OH, 2,2'-O--Ph-Ph-OH, and 2,2'-O-circle-Ph-Ph-OH were determined to be ca. 9.7, ca. 9.7, 6.3, 7.6, 13.7, and 10, respectively. At the same time, the one-electron reduction potentials for 4,4'-O--Ph-Ph-O-circle and 2,2'-HO-Ph-Ph-O-circle were determined to be 0.44 and 1.00 V vs NHE, respectively. By using a thermochemical cycle, the experimentally inaccessible one-electron reduction potentials for 4,4'-HO-Ph-Ph-O-circle and 2,2'-O--Ph-Ph-O-circle were calculated to be 0.64 and 0.78 V vs NHE, respectively. From the redox and acidity data we also estimated the O-H bond dissociation enthalpies for 4,4'-HO-Ph-Ph-OH, 4,4'-O--Ph-Ph-OH, 2,2'-HO-Ph-Ph-OH, and 2,2'-O--Ph-Ph-OH to be 349, 330, 372, and 385 W mol(-1), respectively. The results are discussed in light of previously established substituent effects on the thermochemistry of phenols and phenoxyl radicals.

Place, publisher, year, edition, pages
2002. Vol. 106, no 18, 4758-4762 p.
Keyword [en]
electron-transfer, aqueous-solution, combination reactions, reduction potentials, water
Identifiers
URN: urn:nbn:se:kth:diva-21530DOI: 10.1021/jp0129232ISI: 000175488400040OAI: oai:DiVA.org:kth-21530DiVA: diva2:340228
Note
QC 20100525Available from: 2010-08-10 Created: 2010-08-10 Last updated: 2017-12-12Bibliographically approved

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