Theoretical and Experimental Chemistry

, Volume 34, Issue 2, pp 86–92 | Cite as

Effect of structure on the kinetics of the nucleophilic substitution of acylonium ions

  • V. I. Rybachenko
  • G. Schroeder
  • K. Yu. Chotii
  • V. V. Kovalenko


A study was carried out on 67 reactions involving transfer of acyl groups from the corresponding N-, O-acylonium salts to pyridine N-oxides, highly basic pyridines, and N-methylimidazole in acetonitrile solution. PM3 calculations were carried out for the ionization potentials of the nucleophiles and electron affinities of the N-, O-acylonium cations. A multiparameter correlation was obtained predicting the rate of acyl group transfer.


Ionization Potential Electron Affinity Nucleophilic Substitution Acyl Transfer Physical Organic Chemistry 


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Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • V. I. Rybachenko
    • 1
  • G. Schroeder
    • 1
    • 2
  • K. Yu. Chotii
    • 1
  • V. V. Kovalenko
    • 1
  1. 1.L. M. Litvinenko Institute of Physical Organic and Coal ChemistryNational Academy of Sciences of UkraineDonetskUkraine
  2. 2.Chemistry DepartmentAdam Mickiewicz UniversityPoznanPoland

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