title: Spectroscopic and structural investigation of interaction product of 8-mercaptoquinoline with molecular iodine.
abstract: The behavior of 8-mercaptoquinoline, which is a potential antithyroid drug toward molecular iodine was investigated. The ability of 8-mercaptoquinoline 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=3.14). The crystal structure of the new salt 8-(quinoline-8-yldisulfonyl)quinolinium triiodide - product of irreversible oxidation of 8-mercaptoquinoline was determined by X-ray diffraction. Intramolecular hydrogen bond of N-H⋯N type is presented in the organic cation. The triiodide ion is the nearly centrosymmetrical anion. The 8-(quinoline-8-yldisulfanyl)quinolinium cations form dimers through π-π-stacking interaction between quinolinium rings. The reduced intramolecular interactions are observed between iodine - sulfur atoms and iodine-hydrogen atoms with shortened contacts (less of sum of van-der-waals contacts).
authors.affiliation: Department of Chemistry, Southern Federal University, Zorge St. 7, 344090 Rostov-on-Don, Russia. chernov@sfedu.ru
authors.forename: Margarita S
authors.initials: MS
authors.lastname: Chernov'yants
authors.forename: Zoya A
authors.initials: ZA
authors.lastname: Starikova
authors.forename: Anastasia O
authors.initials: AO
authors.lastname: Karginova
authors.forename: Tatiana S
authors.initials: TS
authors.lastname: Kolesnikova
authors.forename: Alexander Yu
authors.initials: AY
authors.lastname: Tereznikov
mesh_terms: D000042:Absorption; D018360:Crystallography, X-Ray; D004583:Electrons; D007455:Iodine / Q000737:chemistry*; D008968:Molecular Conformation; D011804:Quinolines / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
chemical_list: D011804:Quinolines; C087618:8-mercaptoquinoline; D007455:Iodine
keywords: (1)H; (13)C NMR; 8-Mercaptoquinoline; Charge-transfer complex; Formation constant; UV/vis spectroscopy