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 π-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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Original Russian Text © 2014 E. V. Bartashevich, E. A. Shmanina, I. D. Yushina, D. G. Kim, V. G. Tsirelson.
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Translated from Zhurnal Strukturnoi Khimii, Vol. 55, No. 1, pp. 158–164, January–February, 2014.
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Bartashevich, E.V., Shmanina, E.A., Yushina, I.D. et al. Energy properties and structure of 2- and 8-allylthioquinoline complexes with iodine. J Struct Chem 55, 154–160 (2014). https://doi.org/10.1134/S0022476614010272
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DOI: https://doi.org/10.1134/S0022476614010272