Experimental and quantum chemical study of the reactions of 1,10-anthraquinones with alcohols and amines

Article abstract of DOI:10.1016/0040-4020(95)00046-B

The primary stage of the reaction between 9-aryloxy-1,10-anthraquinones and methanol is the nucleophilic 1,4-addition which gives rise to the adduct, corresponding to 1-hydroxy-9-methoxy-9-aryloxy-10-anthrone. The reaction of 9-aryloxy-1,10-anthraquinones with the primary aliphatic and aromatic amines results in the formation of 9-alkyl(aryl)amino-1,10-anthraquinones that are in a tautomeric equilibrium with 1-hydroxy-9,10-anthraquinone-9-alkyl(aryl)imines. The quantum chemical calculations of the enthalpy of 9-amine-1,10-anthraquinone isomerization are in agreement with the experimentally recorded influence on the tautomeric equilibrium of the nature of amine, solvent, and substituent in the anthraquinone nucleus. The data of quantum chemical calculations confirm the addition-elimination mechanism of the reaction of 1,10-anthraquinones with amines.