title: Characterization of monofluorinated polycyclic aromatic compounds by 1H, 13C and 19F NMR spectroscopy.
abstract: Monofluorinated polycyclic aromatic hydrocarbons (F-PAHs) have attracted much attention in analytical, environmental, toxicological and mechanistic studies because of their physico-chemical properties, which are closely similar to those of the parent PAHs. Because of this, full NMR characterization has become of interest. Complete 1H, 13C and 19F NMR chemical shifts, and also 1J(H,C), (n)J(C,F), (n)J(H,F) and (n)J(H,H) coupling constants, have been assigned for the F-PAHs 1-fluoronaphthalene, 2-fluorofluorene, 5-fluoroacenaphthylene, 2-fluorophenanthrene, 3-fluorophenanthrene, 3-fluorofluoranthene, 1-fluoropyrene, 1-fluorochrysene, 2-fluorochrysene, 3-fluorochrysene and 9-fluorobenzo[k]fluoranthene. To allow comparison with the corresponding parent PAHs, the 1H and 13C chemical shifts of acenaphthylene, phenanthrene, fluoranthene, pyrene and benzo[k]fluoranthene were determined. Chemical shift increments and the effects on the coupling constants from the fluorine substitution are discussed.
authors.affiliation: Department of Chemistry, Norwegian University of Science and Technology (NTNU), NO-7491 Trondheim, Norway. bjartl@nt.ntnu.no
authors.forename: Bjart Frode
authors.initials: BF
authors.lastname: Lutnaes
authors.forename: Gregor
authors.initials: G
authors.lastname: Luthe
authors.forename: Udo A Th
authors.initials: UA
authors.lastname: Brinkman
authors.forename: Jon E
authors.initials: JE
authors.lastname: Johansen
authors.forename: Jostein
authors.initials: J
authors.lastname: Krane
mesh_terms: D002247:Carbon Isotopes; D005461:Fluorine; D017611:Fluorine Compounds / Q000032:analysis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008968:Molecular Conformation; D011084:Polycyclic Aromatic Hydrocarbons / Q000032:analysis* / Q000737:chemistry*; D011522:Protons
chemical_list: D002247:Carbon Isotopes; D017611:Fluorine Compounds; D011084:Polycyclic Aromatic Hydrocarbons; D011522:Protons; D005461:Fluorine