Electronic structures and electrophilic substitution in 2-(4-R-2-quinolyl)thiophenes and 5-(4-R-2-quinolyl)-2,2′-dithienyls

The electronic structures and reactivity indexes (RI) of 2-(4-R-2-quinolyl)thiophenes and 5-(4-R-2-quinolyl)-2,2-dithienyls (R = H, COOH, COOC₂H₅, and NHCOCH₃) and their protonated forms were calculated by the Pariser-Parr-Pople (PPP) method. The peculiarities of the geometrical and -electron structures were established. The calculated reactivity indexes are compared with experimental data on the electrophilic substitution reactions of the investigated compounds. A qualitative agreement between the calculated values and the experimental data was established. It is shown that quinoline derivatives of thiophene are less reactive than the corresponding dithienyl compounds in electrophilic substitution reactions.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 751–754, June, 1979.