title: Synthesis and structure of interaction products of quinoline-2(1H)-thione with molecular iodine.
abstract: The behavior of quinoline-2(1H)-thione, which is a potential antithyroid drug toward molecular iodine, was investigated. The ability of quinoline-2(1H)-thione to form the outer-sphere charge-transfer complex C9H7NS·I2 with iodine molecular in dilute chloroform solution has been studied by UV-vis spectroscopy (lgβ=3.85). The crystal structure of the new salt 2-(quinoline-2-yldisulfanyl)quinolinium triiodide - product of irreversible oxidation of quinoline-2(1H)-thione was determined by X-ray diffraction. The 2-(quinoline-2-yldisulfanyl)quinolinium cations form dimers through π-π-stacking interaction between quinoline rings. Strong intramolecular interactions are observed between iodine - sulfur atoms and iodine - hydrogen atoms with shortened contacts (less of sum of van der Waals contacts). It is noteworthy that two perfectly centrosymmetrical anions I3(-) form a very short contact I(3)⋯I(3') 3.7550(5) so we can state the formation of the dianion I(6)(2-). Therefore the formation and topology of polyiodide species depend on the characteristics, such as shape, size and charge, etc., of the counter cation, 2-(quinoline-2-yldisulfanyl)quinolinium, which is considered as templating agent.
authors.affiliation: Department of Chemistry, Southern Federal University, Zorge St. 7, 344090 Rostov-on-Don, Russia. Electronic address: chernov@sfedu.ru.
authors.forename: Margarita S
authors.initials: MS
authors.lastname: Chernov'yants
authors.affiliation: A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Vavilova St. 28, 119991 Moscow, Russia.
authors.forename: Zoya A
authors.initials: ZA
authors.lastname: Starikova
authors.affiliation: Department of Chemistry, Southern Federal University, Zorge St. 7, 344090 Rostov-on-Don, Russia.
authors.forename: Tatiana S
authors.initials: TS
authors.lastname: Kolesnikova
authors.affiliation: Department of Chemistry, Southern Federal University, Zorge St. 7, 344090 Rostov-on-Don, Russia.
authors.forename: Anastasia O
authors.initials: AO
authors.lastname: Karginova
authors.affiliation: Department of Physics, Southern Federal University, Zorge St. 5, 344090 Rostov-on-Don, Russia.
authors.forename: Nikolay V
authors.initials: NV
authors.lastname: Lyanguzov
mesh_terms: D002725:Chloroform / Q000737:chemistry; D018360:Crystallography, X-Ray; D019281:Dimerization; D004583:Electrons; D007455:Iodine / Q000737:chemistry*; D008968:Molecular Conformation; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D012996:Solutions; D013871:Thiones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D011804:Quinolines; D012996:Solutions; D013871:Thiones; D002725:Chloroform; D007455:Iodine; C037219:quinoline
keywords: 2-(quinoline-2-yldisulfanyl)quinolinium triiodide; Charge-transfer complex; IR; Quinoline-2(1H)-thione; Raman spectroscopy; X-ray diffraction