Electrophilic and Nucleophilic Aromatic Substitutions are Mechanistically Similar with Opposite Polarity
Mieczysław Mąkosza
Abstract
Confrontation of the recently formulated general mechanism of nucleophilic substitution in electron-deficient arenes with the well-known mechanism of electrophilic substitution revealed that these fundamental processes are mechanistically identical but proceed according to opposite polarity-an Umpolung relation. In this viewpoint this apparently controversial concept is supported by discussion of a variety of experimental results.
Topics & Concepts
UmpolungElectrophilePolarity (international relations)NucleophileMechanism (biology)ChemistryNucleophilic substitutionSubstitution reactionStereochemistryElectrophilic substitutionMedicinal chemistryPhysicsOrganic chemistryCatalysisBiochemistryCellQuantum mechanicsChemical Reaction MechanismsOrganic Chemistry Cycloaddition ReactionsAsymmetric Synthesis and Catalysis