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Related Experiment Videos

Strain estimates for small-ring cyclic allenes and butatrienes.

Kimberly J Daoust1, Susanna M Hernandez, Kaleen M Konrad

  • 1Department of Chemistry, University of New Hampshire, Durham, New Hampshire 03824, USA.

The Journal of Organic Chemistry
|July 15, 2006
PubMed
Summary

This study estimates strain in cyclic allenes and butatrienes using computational methods. Higher strain correlates with increased reactivity and reduced barriers for enantiomer interconversion in cyclic allenes.

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Physical Chemistry

Background:

  • Cyclic allenes and butatrienes are strained organic molecules.
  • Understanding strain is crucial for predicting reactivity and stability.

Purpose of the Study:

  • To estimate the strain energy of homologous series of cyclic allenes and butatrienes.
  • To investigate the relationship between strain and the barriers to enantiomeric interconversion in cyclic allenes.

Main Methods:

  • Isodesmic and homodesmic equations were employed at the B3LYP/6-311+G(d,p)+ZPVE level of theory.
  • A fragment deformation approach was utilized, showing improved accuracy for larger ring systems.

Main Results:

  • Strain estimates for cyclic allenes range from 2 kcal/mol (1,2-cyclononadiene) to 65 kcal/mol (1,2-cyclobutadiene).

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  • Strain estimates for cyclic butatrienes range from 4 kcal/mol (1,2,3-cyclononatriene) to over 100 kcal/mol (1,2,3-cyclobutatriene).
  • Barriers to enantiomer interconversion in cyclic allenes decrease with increasing strain, with values below 1 kcal/mol for 1,2-cyclopentadiene.

    • Conclusions:

    • The calculated strain levels correlate with the known reactivity patterns of these cyclic systems.
    • Computational methods provide valuable insights into the energetics and properties of strained cyclic hydrocarbons.