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

Adrienn Simon, Csaba Ballai, G. Lente, I. Fábián

Research output: Contribution to journalArticle

21 Citations (Scopus)

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 21 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).

Original languageEnglish
Pages (from-to)235-241
Number of pages7
JournalNew Journal of Chemistry
Volume35
Issue number1
DOIs
Publication statusPublished - Jan 2011

Fingerprint

Chlorophenols
Cerium
Chlorine
Phenol
Oxidation
Phenols
Chemical shift
Stoichiometry
Protons
Rate constants
Carbon
Nuclear magnetic resonance
Electrons

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Materials Chemistry

Cite this

Structure-reactivity relationships and substituent effect additivity in the aqueous oxidation of chlorophenols by cerium(iv). / Simon, Adrienn; Ballai, Csaba; Lente, G.; Fábián, I.

In: New Journal of Chemistry, Vol. 35, No. 1, 01.2011, p. 235-241.

Research output: Contribution to journalArticle

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