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Issue 1, 2011
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Structure–reactivity relationships and substituent effect additivity in the aqueous oxidation of chlorophenols by cerium(iv)

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Abstract

The oxidation of all 19 chlorophenols and unsubstituted phenol by cerium(IV) was studied in an acidic aqueous solution in order to carry out a systematic test of chlorine substituent effects on the reactivity. All reactions were found to show 2 ∶ 1 cerium(IV)  ∶ phenol stoichiometry and a simple second-order rate equation. Rate constants did not correlate well with characteristic parameters such as pK values, carbon-13 NMR chemical shifts or Hammett substituent constants. Nevertheless, a strict additivity of chlorine substituent effects was found in both characteristic and reactivity parameters. The data suggest that a proton-coupled electron transfer mechanism could be operative. 2,4,6-Trichlorophenol was found to show exceptionally high reactivity towards cerium(IV).

Graphical abstract: Structure–reactivity relationships and substituent effect additivity in the aqueous oxidation of chlorophenols by cerium(iv)

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Supplementary files

Article information


Submitted
06 Jul 2010
Accepted
01 Oct 2010
First published
25 Oct 2010

New J. Chem., 2011,35, 235-241
Article type
Paper

Structure–reactivity relationships and substituent effect additivity in the aqueous oxidation of chlorophenols by cerium(IV)

A. Simon, C. Ballai, G. Lente and I. Fábián, New J. Chem., 2011, 35, 235
DOI: 10.1039/C0NJ00529K

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