Aromaticity and Electrophilic Aromatic Substitution

  • Francis A. Carey
  • Richard J. Sundberg


The meaning of the word aromaticity has evolved as understanding of the reason for the special properties of benzene and other aromatic molecules has deepened. Originally, aromaticity was associated with a special chemical reactivity.1 The aromatic hydrocarbons were considered to be those unsaturated systems that underwent substitution reactions in preference to addition. Later, the idea of special stability came to play a larger role. Benzene can be shown to be much lower in enthalpy than predicted by summation of the normal bond energies for the C=C, C-C, and C-H bonds present in the Kekulé representation of benzene. Aromaticity has now been generally equated with this property of lowered molecular energy. A major contribution to the stability of the aromatic systems is recognized as being due to the delocalized nature of the electrons in these molecules.


Isotope Effect Kinetic Isotope Effect Electrophilic Substitution Substrate Selectivity Electrophilic Aromatic Substitution 
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

© Plenum Press, New York 1977

Authors and Affiliations

  • Francis A. Carey
    • 1
  • Richard J. Sundberg
    • 1
  1. 1.University of VirginiaCharlottesvilleUSA

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