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Why are reactions of 2‐ and 8‐thioquinoline derivatives with iodine different?
Author(s) -
Rudakov Boris V.,
Stash Adam I.,
Makarov Gennady I.,
Matveychuk Yury V.,
Zherebtsov Dmitry A.,
Bartashevich Ekaterina V.
Publication year - 2018
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229618009385
Subject(s) - iodine , quinoline , triiodide , chemistry , iodide , dication , crystal structure , medicinal chemistry , stereochemistry , crystallography , molecule , organic chemistry , electrode , dye sensitized solar cell , electrolyte
The crystal structures of 1,2‐dihydro‐1,1′‐bi[thiazolo[3,2‐ a ]quinoline]‐10a,10a′‐diium diiodide hemihydrate, C 22 H 16 N 2 S 2 2+ ·2I − ·0.5H 2 O, and 1,2‐dihydro‐1,1′‐bi[thiazolo[3,2‐ a ]quinoline]‐10a,10a′‐diium iodide triiodide, C 22 H 16 N 2 S 2 2+ ·I − ·I 3 − , obtained during the reaction of 1,4‐bis(quinolin‐2‐ylsulfanyl)but‐2‐yne (2TQB) with iodine, have been determined at 120 K. The crystalline products contain the dication as a result of the reaction proceeding along the iodocyclization pathway. This is fundamentally different from the previously observed reaction of 1,4‐bis(quinolin‐8‐ylsulfanyl)but‐2‐yne (8TQB) with iodine under similar conditions. A comparative analysis of the possible conformational states indicates differences in the relative stabilities and free rotation for the 2‐ and 8‐thioquinoline derivatives which lead to a disparity in the convergence of the potential reaction centres for 2TQB and 8TQB.