EXPERIMENTAL AND QUANTUM-CHEMICAL STUDY OF THE REACTIONS OF 1,10-ANTHRAQUINONES WITH ALCOHOLS AND AMINES

The primary stage of the reaction between 9-aryloxy-1,10-anthraquinone s and methanol is the nucleophilic 1,4-addition which gives rise to th e adduct, corresponding to 1-hydroxy-9-methoxy-9-aryloxy-10-anthrone. The reaction of 9-aryloxy-1,10-anthraquinones with the primary aliphat ic and aromatic amines results in the formation of 9-alkyl(aryl)aminol -1,10-anthraquinones that are in a tautomeric equilibrium with 1-hydro xy-9,10-anthraquinone-9-alkyl(aryl)imines. The quantum chemical calcul ations of the enthalpy of 9-amine-1,10-anthraquinone isomerization are in agreement with the experimentally recorded influence on the tautom eric equilibrium of the nature of amine, solvent, and substituent in t he anthraquinone nucleus. The data of quantum chemical calculations co nfirm the addition-elimination mechanism of the reaction of 1,10-anthr aquinones with amines.