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Kinetics and Catalysis

, Volume 42, Issue 4, pp 471–473 | Cite as

Kinetics of the Reactions of 4-Nitrochlorobenzene with Substituted Phenols in the Presence of Potassium Carbonate

  • V. I. Mil'to
  • V. Yu. Orlov
  • G. S. Mironov
  • V. V. Kopeikin
Article

Abstract

The kinetics of 4-nitrochlorobenzene (4-NCB) reactions with substituted phenols in the presence of potassium carbonate in N,N-dimethylacetamide was studied. Depending substituents, the reactivity of the phenols is changed in the series 3-NO2> 4-Cl > H > 4-Br > 3-CH3> 3-NH2, which is consistent with the series of their acidity. The reaction rates satisfactorily correlate with the pKavalues of the corresponding substituted phenols. Based on kinetic data (first-order and zero-order reactions with respect to phenol and 4-NCB, respectively, and the consistency of the reactivity and acidity of substituted phenols), the deprotonation of phenols is considered as the rate-determining step of the overall reaction under the test conditions. A reaction scheme was proposed for the synthesis of diaryl ethers in the presence of potassium carbonate. It involves a heterogeneous step of phenol deprotonation, which takes place on the surface of potassium carbonate, and a homogeneous step of the interaction of potassium phenolates with 4-NCB. Under the reaction conditions, the resulting bicarbonate decomposes with the formation of potassium carbonate and with the release of carbon dioxide and water.

Keywords

Ether Dioxide Phenol Carbon Dioxide Acidity 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© MAIK “Nauka/Interperiodica” 2001

Authors and Affiliations

  • V. I. Mil'to
    • 1
  • V. Yu. Orlov
    • 1
  • G. S. Mironov
    • 1
  • V. V. Kopeikin
    • 1
  1. 1.Yaroslavl State UniversityYaroslavlRussia

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