ENERGY PROPERTIES AND STRUCTURE OF 2AND 8-ALLYLTHIOQUINOLINE COMPLEXES WITH IODINE
E. V. Bartashevich1, E. A. Shmanina1, I. D. Yushina1, D. G. Kim2, V. G. Tsirelson3
1Chemistry Department, South Ural State University, Chelyabinsk, Russia
2Chemistry Department, South Ural State University
3D. I. Mendeleev University of Chemical Technology, Moscow, Russia
Keywords: галогенные связи, иод, комплексы с переносом заряда, энергия взаимодействия, halogen bonds, iodine, charge-transfer complexes, interaction energy
Abstract
The study focuses on the energy and quantum topological properties of substituted 2- and 8-allylthioquinoline complexes with iodine, which are assumed to correspond to prereaction states in the iodocyclization reaction leading to the formation of thiazolo- and tiazinoquinoline systems. The structures of the complexes and the corresponding atomic interactions are modeled considering the different conformational states of allyl-substituted quinolinethiols (thioquinolines). The energy values are analyzed for the interactions between the iodine molecule and different donor centers of the substituted quinoline system: the nitrogen heteroatom, sulfur, and p-system of the allyl group. It is shown that the formation of stable complexes with the nitrogen of the quinoline ring is complicated by steric hindrances posed by the S-allyl group at positions 2 and 8 of the quinoline system, which in turn contributes to the convergence of the cyclization centers.
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