Quantum chemical study of ferrocene derivatives 2. Arylation reactions with aminophenols

Abstract

Using the Hartree–Fock approximation and within the framework of the density functional theory (DFT) with the B3LYP functional in the 3-21G basis we carried out quantum chemical calculations of ferrocene molecules having a non-benzoid aromatic nature and products of its arylation by o-, m-, and p-aminophenols, leading to ferrocenylphenols. The process yields were strongly dependent on the specific aminophenol isomer. We analyzed the causes of these differences and the role of solvation effects. We demonstrated that the aromaticity condition, which presumes a planar positioning of atoms in cyclic structures, as well as the Hückel rule, are met. The reasons for the multiple reactivity of the ferrocene molecule and the relatively high yield of the p-product in a diethyl ether medium are discussed.