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Related Experiment Videos

Fluorobenzene-nucleobase interactions: hydrogen bonding or pi-stacking?

Roman Leist1, Jann A Frey, Samuel Leutwyler

  • 1Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.

The Journal of Physical Chemistry. A
|March 24, 2006
PubMed
Summary

This study reveals that 2-pyridone and fluorobenzene form stable hydrogen bonds, challenging previous assumptions of pi-stacking. Spectroscopic analysis confirms these hydrogen bonds, providing insights into molecular interactions in modified DNA systems.

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Area of Science:

  • Molecular Spectroscopy
  • Supramolecular Chemistry
  • Biophysical Chemistry

Background:

  • Previous studies suggested pi-stacking and shape complementarity stabilize interactions between modified DNA and fluorobenzene nucleotides.
  • Hydrogen bonds were thought to be absent due to fluorination on pairing edges.

Purpose of the Study:

  • To investigate the nature of interactions between the nucleobase analogue 2-pyridone and various fluorobenzenes.
  • To determine if these interactions are hydrogen-bonded or pi-stacked.
  • To quantify the strength of these molecular interactions.

Main Methods:

  • Utilized two-color resonant two-photon ionization and fluorescence emission spectroscopies.
  • Analyzed supersonically cooled complexes of 2-pyridone with seven substituted fluorobenzenes.

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  • Employed ab initio calculations to determine spectral shifts and hydrogen-bond dissociation energies.

    • Main Results:

    • Demonstrated that 2-pyridone and fluorobenzene complexes are hydrogen-bonded, not pi-stacked.
    • Observed intermolecular vibrational frequencies characteristic of doubly hydrogen-bonded complexes.
    • Found a linear correlation between spectral blue shifts and calculated hydrogen-bond dissociation energies (D0).

    Conclusions:

    • The interactions between 2-pyridone and fluorobenzenes are primarily hydrogen-bonded.
    • Spectroscopic blue shifts provide a reliable method for estimating hydrogen-bond strengths.
    • The estimated ground-state dissociation energies for these complexes are approximately 6 kcal/mol.