Jump to main content
Jump to site search

Issue 1, 2011
Previous Article Next Article

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

Author affiliations

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)

Back to tab navigation

Supplementary files

Publication details

The article was received on 06 Jul 2010, accepted on 01 Oct 2010 and first published on 25 Oct 2010


Article type: Paper
DOI: 10.1039/C0NJ00529K
Citation: New J. Chem., 2011,35, 235-241
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements