title: Synthesis, spectroscopy and computational studies of selected hydroxyquinolines and their analogues.
abstract: Synthetic, spectroscopy and mechanistic aspects of preparation of selected hydroxyquinolines and their analogues or derivatives contained methoxy, fluoro, chloro, carboxylic, carbodithioic and phosphinate or dioxaphosphinane groups were elaborated. The multinuclear NMR and five single crystal X-ray characteristics of the series of quinolines have been determined. The molecular orbitals of the selected hydroxyquinolines have been calculated by density functional theory. The X-ray and NMR studies of 8-[(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)oxy]-5,7-dibromo-2-methylquinoline and 8-[(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)oxy]-5-fluoro-2-methylquinoline indicate the appearance of anomeric effect.
authors.affiliation: Institute of Chemistry, University of Silesia, ul. Szkolna 9, PL-40007 Katowice, Poland. Electronic address: jnycz@us.edu.pl.
authors.forename: Jacek E
authors.initials: JE
authors.lastname: Nycz
authors.forename: Marcin
authors.initials: M
authors.lastname: Szala
authors.forename: Grzegorz J
authors.initials: GJ
authors.lastname: Malecki
authors.forename: Maria
authors.initials: M
authors.lastname: Nowak
authors.forename: Joachim
authors.initials: J
authors.lastname: Kusz
mesh_terms: D003460:Crystallization; D018360:Crystallography, X-Ray; D006912:Hydroxyquinolines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D055672:Static Electricity; D014961:X-Ray Diffraction
chemical_list: D006912:Hydroxyquinolines
keywords: Anomeric effect; Carboxylic acid; Halogen; Hydroxyquinoline; Quinoline; Skraup–Doebner–Miller