Inter- and intramolecular hydrogen bonding in phenol derivatives: A model system for poly-L-tyrosine

Neil T. Hunt, Andrew R. Turner, Klaas Wynne

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The ultrafast dynamics of solutions of phenol and two phenol derivativesshydroquinone (1,4-benzenediol) and pyrocatechol (1,2-benzenediol)shave been studied with Optically Heterodyne-Detected Optical Kerr-Effect (OHD-OKE) spectroscopy. The solvents, methanol and acetonitrile, were selected to provide strong and weak solvent-solute hydrogen-bonding interactions, respectively, while pyrocatechol features an intramolecular hydrogen bond. Together these provide a series of model systems for polypeptides such as polytyrosine, which facilitate the direct study of inter- and intramolecular hydrogen bonding. A broad contribution to the Raman spectral density of the methanol solutions at frequencies between 150 and 300 cm-1 has been observed that is absent in acetonitrile. This contribution has been assigned to solvent-solute hydrogen-bond stretching vibrations. The OHD-OKE response of poly-L-tyrosine has been measured and was found to contain a similar contribution. Density functional theory geometry optimizations and normal mode calculations have been performed using the B3LYP hybrid functional and 6-311++G** basis set. These have yielded a complete assignment of the low-frequency Raman and far-infrared spectra of pyrocatechol for the first time, which has provided information on the nature of the intramolecular hydrogen bond of pyrocatechol.
Original languageEnglish
Pages (from-to)19008-19017
Number of pages9
JournalJournal of Physical Chemistry B
Volume109
Issue number40
DOIs
Publication statusPublished - 10 Aug 2005

Keywords

  • inter- and intramolecular hydrogen bonding
  • phenol derivatives
  • poly-L-tyrosine
  • nanoscience

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