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Van der Waals Interactions01:24

Van der Waals Interactions

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Atoms and molecules interact with each other through intermolecular forces. These electrostatic forces arise from attractive or repulsive interactions between particles with permanent, partial, or temporary charges. The intermolecular forces between neutral atoms and molecules are ion–dipole, dipole–dipole, and dispersion forces, collectively known as van der Waals forces.
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This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
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Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen...
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Intermolecular forces are attractive forces that exist between molecules. They dictate several bulk properties, such as melting points, boiling points, and solubilities (miscibilities) of substances. Molar mass, molecular shape, and polarity affect the strength of different intermolecular forces, which influence the magnitude of physical properties across a family of molecules.
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Facile Preparation of Internally Self-assembled Lipid Particles Stabilized by Carbon Nanotubes
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Dispersion interaction stabilizes sterically hindered double fullerenes.

Jun Zhang1, Michael Dolg

  • 1Institute for Theoretical Chemistry, University of Cologne, Address Greinstr. 4, 50939 Cologne. zhangjunqcc@gmail.com.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 29, 2014
PubMed
Summary

Dispersion interactions, not just steric hindrance, dictate stereochemistry for bulky molecules like fullerenes. This quantum chemistry study reveals compact isomers are more stable, impacting product prediction in organic synthesis.

Keywords:
dispersion interactionsfullerenesisomer stabilitysteric effectsvan der Waals forces

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Stereochemistry

Background:

  • Steric effects traditionally dominate stereochemical outcomes in bulky molecular systems.
  • The role of attractive dispersion forces in influencing stereochemistry is often underestimated.

Purpose of the Study:

  • To investigate the impact of dispersion interactions on the stereochemistry of bulky functional groups.
  • To re-evaluate the predicted stereochemical outcome for a double C60 adduct of pentacene.

Main Methods:

  • Utilized state-of-the-art quantum chemical methods for calculations.
  • Compared results with and without the inclusion of dispersion interactions.

Main Results:

  • Attractive dispersion forces were found to be more influential than repulsive steric effects for bulky groups (cyclohexane, fullerenes, dodecahedrane, C60).
  • The compact syn isomer of the double C60 adduct of pentacene 1 is predicted to be the major product, contrary to previous experimental inference.
  • Gibbs energy difference (ΔG(syn-anti)) was calculated as -6.36 kcal/mol with dispersion and +1.15 kcal/mol without.

Conclusions:

  • Dispersion interactions play a critical role in determining stereochemical phenomena, sometimes overriding steric considerations.
  • This highlights the importance of including dispersion forces in computational studies for accurate prediction of molecular stability and reactivity.
  • The findings necessitate a re-examination of stereochemical outcomes in complex organic synthesis involving large molecular fragments.