Influence of solvents on the kinetics of the reaction of benzyl chloride with methacrylic acid in the presence of tertiary amines

  • K. A. Charushnikov
  • M. A. Bulatov
  • L. G. Surovtsev
Physical Chemistry
  • 51 Downloads

Conclusions

  1. 1.

    The direction of the reaction of benzyl chloride with methacrylic acid in the presence of tertiary amines depends on the basicity of the amine. In the presence of highly basic amines, benzyl methacrylate is formed. Weakly basic amines are alkylated by benzyl chloride.

     
  2. 2.

    Aprotonic polar solvents accelerate the formation of the ester. The reaction rate constant correlates with the dielectric constant ɛ of the solvent according to the Kirkwood and Amis equations for the reaction of two dipoles.

     
  3. 3.

    An hypothesis of a push-pull SN2 mechanism in media with a low or moderate value of ɛ and replacement of this mechanism by an SN1 mechanism in media with a high value of ɛ has been advanced.

     

Keywords

Chloride Ester Dielectric Constant Methacrylate Benzyl 

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Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • K. A. Charushnikov
    • 1
  • M. A. Bulatov
    • 1
  • L. G. Surovtsev
    • 1
  1. 1.Institute of ChemistryAcademy of Sciences of the USSR, Ural Scientific CenterSverdlovsk

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