Quantum-chemical study on the relation between thermodynamic parameters in the iodination of benzene with N-I and O-I reagents and pK a values of the corresponding NH and oh acids

Abstract

Thermodynamic parameters of direct iodination of benzene with several iodinating agents were calculated using semiempirical (PM3), ab initio (3-21G**), and DFT (B3LYP/LanL2DZ) methods, as well as in terms of the polarization continuum model (PCM or Tomasi model). A close to linear correlation was found between the calculated thermodynamic parameters (ΔH ≠ , ΔG ≠ ) and pKT and experimental pKa values of acids whose anions are incorporated into iodine-containing intermediates.