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Intramolecular Nonbonded Attractive Interactions: 1-Substituted Propenes.

Kenneth B Wiberg1, Yi-Gui Wang1, George A Petersson1

  • 1Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459-0180, and Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060.

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Summary
This summary is machine-generated.

Certain cis-alkenes are more stable than their trans counterparts due to attractive forces overcoming steric repulsion. This finding challenges typical alkene stability trends, offering new insights into molecular interactions.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Physical Chemistry

Background:

  • Typically, trans-alkenes are more stable than cis-alkenes due to reduced steric hindrance.
  • However, specific 1-substituted propenes exhibit an inversion of this stability trend.

Purpose of the Study:

  • To investigate the factors contributing to the unusual stability of certain cis-1-substituted propene isomers.
  • To quantify the interplay of steric, electrostatic, and dispersive forces in determining alkene stability.

Main Methods:

  • Computational chemistry methods were employed to calculate the structures and energies of cis- and trans-isomers.
  • Second-order Møller–Plesset perturbation theory (MP2) was used to calculate pair energies, quantifying dispersive interactions.
  • A comprehensive model summing steric, electrostatic, and dispersive interactions was developed.

Main Results:

  • Calculations revealed steric repulsion in cis-isomers, which is counteracted by attractive forces.
  • For fluoro (F) and methoxy (OMe) substituents, Coulombic interactions were found to stabilize cis-isomers.
  • For chloro (Cl) and bromo (Br) substituents, attractive dispersive interactions were identified as the stabilizing factor.
  • The summation of calculated steric, electrostatic, and dispersive interactions accurately reproduced observed energy differences.

Conclusions:

  • The stability of cis-1-substituted propenes is governed by a delicate balance of repulsive and attractive forces.
  • Electrostatic and dispersive interactions can overcome steric repulsion, leading to cis-isomer stability.
  • Computational methods, including MP2 energy calculations, provide accurate insights into these molecular interactions.