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ESR study of kinetic acidity of 6-tert-butyl-2-hydroxy-4-triphenylmethylphenoxyl

Abstract

Thermodynamic and kinetic acidities of 6-tert-butyl-2-hydroxy-4-triphenylmethylphenoxyl during its interaction with triethylamine in toluene have been studied by ESR. It has been shown that the protolysis of this radical is a two-pathway process, since tautomeric transitions, i.e. ammonium ion migration between oxygen atoms of the semiquinone radical anion, have been detected in the reaction products, that is, in contact ion pairs of the corresponding semiquinone radicals.

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No 1, pp. 81–84, January, 1993.

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Masalimov, A.S., Melbardis, L.E. & Prokof'ev, A.I. ESR study of kinetic acidity of 6-tert-butyl-2-hydroxy-4-triphenylmethylphenoxyl. Russ Chem Bull 42, 71–74 (1993). https://doi.org/10.1007/BF00699977

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Key words

  • 6-tert-butyl-2-hydroxy-4-triphenylmethylphenoxyl
  • triethylamine
  • kinetic acidity
  • ESR spectra
  • kinetic and thermodynamic parameters
  • proton transfer