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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KTH, Superseded Departments, Chemistry.ORCID iD: 0000-0003-0663-0751
KTH, Superseded Departments, Chemistry.
KTH, Superseded Departments, Chemistry.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, p. 4758-4762Article 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, p. 4758-4762
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, id: diva2:340228
Note
QC 20100525Available from: 2010-08-10 Created: 2010-08-10 Last updated: 2017-12-12Bibliographically approved

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