Dediazoniations of Arenediazonium Ions. Part 26. Influence of Substituents on the Formation of Benzoic Acids in Reactions of Aryl-Cation-Type Intermediates with CO

Article abstract of DOI:10.1002/hlca.19880710303

The N2-molecule-aryl-cation pair formed as the first intermediate in dediazoniations of arenediazonium ions can be trapped with CO in H2O with formation of the corresponding arenecarboxylic acids.This reaction is considered as a model for the reverse of dediazoniation, since CO is isoelectronic with N2.The evaluation of the yields of arenecarboxylic acids formed from substituted benzenediazonium ions using Taft's dual substituent parameter treatment demonstrates that the field reaction constant ρ_F and the resonance reaction constant ρ_R are positive and negative, respectively, as expected for a reaction which corresponds electronically to the addition of N2 to aryl cations.