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Issue 9, 1993
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O–H bond strengths and one-electron reduction potentials of multisubstituted phenols and phenoxyl radicals. Predictions using free energy relationships

Abstract

General equations for the empirical determination of relative O–H bond strengths and one-electron reduction potentials of multisubstituted phenols and phenoxyl radicals are derived. The derivations are based on data from direct and indirect measurements of phenolic O–H bond strengths, and one-electron reduction potential measurements using electrochemical and radiation chemical methods. The resulting equations are ΔD(O–H)=–1.97 + 29.87 ∑σ+(kJ mol)–1 and E°= 0.79 + 0.34 ∑σ+(V vs. NHE) where ∑σ+ is the sum of the Brown substituent values (σo+= 0.66 σp+, σm+ and σp+). The conditional relationship σo+= 0.66 σp+ is also derived in this work.

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Article type: Paper
DOI: 10.1039/P29930001567
Citation: J. Chem. Soc., Perkin Trans. 2, 1993,0, 1567-1568
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    O–H bond strengths and one-electron reduction potentials of multisubstituted phenols and phenoxyl radicals. Predictions using free energy relationships

    M. Jonsson, J. Lind, T. E. Eriksen and G. Merényi, J. Chem. Soc., Perkin Trans. 2, 1993, 0, 1567
    DOI: 10.1039/P29930001567

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