Attila Kovács, Vladislav Izvekov, Gábor Keresztury, Claus J. Nielsen, Peter Klæboe

Vibrational Spectroscopic Study of 2-Fluorophenol and 2,3,5,6-Tetrafluorohydroquinone

Chemical Physics, 335 (2007) 205-214

The vibrational properties of two fluorophenol derivatives, 2-fluorophenol (1) and 2,3,5,6-tetrafluorohydroquinone (2), have been studied by FT-IR and FT-Raman spectroscopy. The spectra revealed the existence of two conformers for both compounds. A quantum chemical study of the title compounds was carried out at the B3LYP/6-311++G** level of theory. The computed harmonic force fields were scaled utilizing previously developed scale factors resulting in good agreement with experiment and facilitating the assignment of the vibrational spectra and a distinction between the two conformers. The wavenumbers of identified OH torsional modes support a stronger intramolecular O–H…F hydrogen bonding in 1 than in 2.

The vibrational spectra (top: FT-IR of the vapour, bottom: FT-Raman of the liquid) of 2-fluorophenol (1).

The vibrational spectra (top: FT-IR, bottom: FT-Raman) of solid 2,3,5,6-tetrafluorohydroquinone (2).