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Medium-sized rings: conformational preferences in cyclooctanone driven by transannular repulsive interactions.

Ecaterina Burevschi1, Isabel Peña, M Eugenia Sanz

  • 1Department of Chemistry, King's College London, SE1 1DB London, UK. maria.sanz@kcl.ac.uk.

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The conformational landscape of cyclooctanone was studied using rotational spectroscopy. The dominant boat-chair conformation was identified, revealing new insights into medium-sized ring dynamics and interactions.

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Area of Science:

  • Physical chemistry
  • Molecular spectroscopy
  • Computational chemistry

Background:

  • Conformational analysis of medium-sized rings is crucial for understanding intramolecular interactions and chemical reactivity.
  • Cyclooctanone, an eight-membered cyclic ketone, presents a complex conformational profile due to its ring size.

Purpose of the Study:

  • To characterize the conformational landscape of cyclooctanone.
  • To determine the precise geometric parameters of its stable conformers.
  • To investigate the driving forces behind its conformational preferences.

Main Methods:

  • Broadband rotational spectroscopy was employed to probe the molecular structure.
  • Quantum-chemistry calculations were used to support experimental findings and predict conformer energies.
  • Analysis of spectroscopic parameters provided detailed structural information.

Main Results:

  • Three distinct conformers of cyclooctanone were identified: two boat-chair and one twisted boat-chair.
  • The global minimum is a boat-chair conformation, with its bond lengths and angles determined for the first time.
  • The boat-chair conformer is significantly more abundant (40:1) than the next most stable twisted boat-chair conformer.

Conclusions:

  • The conformational preferences of cyclooctanone are primarily governed by the minimization of repulsive non-bonded transannular interactions.
  • The study provides a detailed understanding of the structure and dynamics of medium-sized rings.
  • Rotational spectroscopy combined with computational methods is a powerful tool for conformational analysis.