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Related Experiment Videos

Steric "attraction": not by dispersion alone.

Ganna Gryn'ova1, Clémence Corminboeuf1

  • 1Institut des Sciences et Ingénierie Chimiques, École polytechnique fédérale de Lausanne, CH-1015 Lausanne, Switzerland.

Beilstein Journal of Organic Chemistry
|July 18, 2018
PubMed
Summary

Steric bulk in organic molecules can lead to attraction, not repulsion, due to dispersion and electrostatic forces. This study quantifies electrostatic contributions in various molecular systems, highlighting their importance in both aromatic and aliphatic compounds.

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Area of Science:

  • Computational chemistry
  • Molecular modeling
  • Physical organic chemistry

Background:

  • Non-covalent interactions in sterically hindered molecules are crucial for molecular assembly.
  • Dispersion forces often dominate, but electrostatic contributions are significant.
  • Understanding these forces impacts molecular design and prediction methods.

Purpose of the Study:

  • To quantify the electrostatic stabilization contribution in sterically hindered organic molecules.
  • To investigate the role of charge penetration in both sp2-rich and sp3-rich systems.
  • To assess the impact of bulky substituents (tert-butyl, phenyl, cyclohexyl, adamantyl) on interaction energetics.

Main Methods:

  • Quantum chemical calculations were employed to model molecular dimers.
Keywords:
charge penetrationdispersionhydrocarbonnon-covalent interactionssteric attraction

Related Experiment Videos

  • Diverse molecular cores, including benzene, cyclohexane, and their substituted derivatives, were analyzed.
  • Energetics and equilibrium interaction distances were computed.

    • Main Results:

    • Electrostatic stabilization, arising from charge penetration, significantly influences interaction energies and distances.
    • This effect is substantial in sp2-rich systems and non-negligible in less polarizable sp3-rich systems.
    • Bulky substituents like cyclohexyl and adamantyl enhance electrostatic contributions through short-range CH...HC contacts.

    Conclusions:

    • Electrostatic interactions, particularly charge penetration, play a critical role in sterically hindered systems, complementing dispersion forces.
    • The findings underscore the importance of electrostatic effects in aliphatic systems, often underestimated compared to dispersion.
    • Results have implications for developing accurate force fields and improving crystal structure prediction models.