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

Research paper by P. L. Trakhtenberg, M. N. Zemtsova, A. N. Gusarov, V. P. Zvolinskii, A. E. Lipkin

Indexed on: 01 Jun '79Published on: 01 Jun '79Published in: Chemistry of Heterocyclic Compounds



Abstract

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 π-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.