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Relationship between the electrophilicity of substituting agents and substrate selectivity in Friedel-Crafts reactions

Abstract:

The global electrophilicity index evaluated at the ground state of benzylating and acylating agents shows a quantitative linear relationship with the experimental substrate selectivity index evaluated for a series of Friedel-Crafts reactions. The theoretical scale correctly accounts for the electrophilic activation/deactivation effects promoted by electron withdrawing and electron releasing substituents in these molecules. The pbkp_redicted substrate selectivity values estimated from the knowledge of the electrophilicity index may become accurate to within 10% and less. © 2004 Elsevier Ltd. All rights reserved.