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2-Ethynylpyridine dimers: IR spectroscopic and computational study.

Danijela Bakarić1, Jens Spanget-Larsen2

  • 1Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička 54, 10001 Zagreb, Croatia.

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Summary

This study reveals that 2-ethynylpyridine (2-EP) forms hydrogen-bonded dimers in solution, primarily through π-stacking and CH⋯N interactions. These findings clarify the self-assembly behavior of this versatile molecule.

Keywords:
2-ethynylpyridineHydrogen bondingIR spectroscopyMultifunctionalityQuantum chemical calculations

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Area of Science:

  • Physical Chemistry
  • Supramolecular Chemistry
  • Spectroscopy

Background:

  • 2-ethynylpyridine (2-EP) possesses multiple functional groups capable of participating in hydrogen bonding.
  • Understanding the self-assembly and aggregation behavior of 2-EP is crucial for its applications.
  • Previous studies have not fully elucidated the specific dimer structures and interactions of 2-EP in solution.

Purpose of the Study:

  • To investigate the dimer structures and intermolecular interactions of 2-ethynylpyridine (2-EP) in tetrachloroethene.
  • To determine the distribution and stability of different 2-EP dimer configurations.
  • To quantify the dimerization process using spectroscopic and computational methods.

Main Methods:

  • Infrared (IR) spectroscopy was employed to monitor changes in vibrational frequencies associated with monomer and dimer formation.
  • Derivative spectroscopy was utilized to resolve overlapping spectral bands.
  • Quantum chemical calculations (B3LYP+D3 with counterpoise correction) were performed to predict stable dimer structures and interaction energies.

Main Results:

  • Experimental evidence showed the formation of hydrogen-bonded complexes involving the CH moiety of 2-EP, indicated by a red shift in the CH stretching vibration.
  • Derivative spectroscopy resolved dimer-specific bands for both CH and CC stretching vibrations.
  • Computational analysis identified π-stacked dimers and dimers with intermolecular CH⋯N hydrogen bonding as the most stable configurations, with predicted CH red shifts of 54-120 cm⁻¹.

Conclusions:

  • 2-ethynylpyridine predominantly forms π-stacked dimers and dimers stabilized by CH⋯N hydrogen bonds in tetrachloroethene.
  • The study provides quantitative data on dimerization, estimating the dimerization constant (K₂) at 0.13 ± 0.01 dm³/mol at 25°C.
  • The findings highlight the importance of CH⋯N hydrogen bonding and π-π interactions in the self-assembly of 2-EP.