10.1007/BF00510097
The study investigates the basicity constants and transformations of pyrylium and pyridinium salts containing p-aminophenyl substituents. The chemicals involved include 2,6-diphenyl-4-(p-aminophenyl)pyrylium perchlorate (I), 2,6-diphenyl-4-(p-aminophenyl)pyridine (II), 2,6-diphenyl-4-(p-aminophenyl)pyridinium perchlorates (IV and V), 4-(p-aminophenyl)flavylium perchlorate (VI), and 2,4,6-triphenylpyridine (VII). The study shows that the positive charge in the pyrylium cation is higher than in the pyridinium cation, as indicated by the basicity constants measured in absolute acetonitrile. The study also examines the reactions of these salts with electrophilic and nucleophilic reagents, revealing that the pyrylium salts readily undergo acetylation and form azomethines with benzaldehyde, while the pyridinium salts show different reactivity patterns. Additionally, the study explores the diazotization of perchlorate I and its subsequent reactions to form various derivatives, highlighting the significant electronic effects of the pyrylium and pyridinium rings on the reactivity of the amino group.