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Related Experiment Videos

Overcrowding motifs in large PAHs. An ab initio study.

Sergey Pogodin1, Israel Agranat

  • 1Department of Organic Chemistry, The Hebrew University of Jerusalem, Jerusalem 91904, Israel.

The Journal of Organic Chemistry
|January 5, 2002
PubMed
Summary

This study investigated large polycyclic aromatic hydrocarbons (LPAHs) using ab initio methods. Overcrowded structures, particularly those with two cove regions, were found to be more stable than planar isomers, especially in larger systems.

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Large polycyclic aromatic hydrocarbons (LPAHs) are complex molecules with unique electronic and structural properties.
  • Understanding the stability and conformations of overcrowded LPAHs is crucial for predicting their behavior and potential applications.

Purpose of the Study:

  • To investigate the structural and energetic properties of planar and overcrowded LPAHs.
  • To compare the stability of different overcrowded conformations, specifically those with cove and fjord regions.
  • To analyze the influence of molecular size on overcrowding effects.

Main Methods:

  • Ab initio calculations using Hartree-Fock (HF) and Density Functional Theory (DFT) with the B3LYP functional.
  • Geometry optimization to determine minimum energy conformations.

Related Experiment Videos

  • Calculation of total energies and heats of formation.

    • Main Results:

    • The most stable isomers in both C(34)H(18) and C(38)H(18) series were found to be planar.
    • Among overcrowded LPAHs, twisted-folded structures with two cove regions were more stable than those with one fjord region.
    • Energy differences between planar and overcrowded isomers decreased with increasing number of aromatic rings, indicating enhanced stability in larger LPAHs.
    • Overcrowded twisted-folded C(2)-7 was found to be more stable than its planar isomer, highlighting the role of aromatic stabilization.

    Conclusions:

    • Overcrowding in LPAHs can lead to stable, non-planar conformations, especially in larger systems.
    • The presence of multiple 'cove' regions enhances stability in overcrowded LPAHs compared to 'fjord' regions.
    • Ab initio methods provide valuable insights into the complex interplay of aromaticity and steric strain in large polycyclic aromatic hydrocarbons.