Characterization of monofluorinated polycyclic aromatic compounds by 1H, 13C and 19F NMR spectroscopy

✍ Scribed by Bjart Frode Lutnaes; Gregor Luthe; Udo A. Th. Brinkman; Jon E. Johansen; Jostein Krane

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 127 KB
• Volume: 43
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1584

✦ Synopsis

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 ^1^H, ^13^C and ^19^F NMR chemical shifts, and also ^1^J(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 ^1^H and ^13^C 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. Copyright © 2005 John Wiley & Sons, Ltd.