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Conformations of Ethane and Propane02:18

Conformations of Ethane and Propane

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In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered...
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Newman Projections02:06

Newman Projections

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Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as...
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Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
16.7K
Fischer Projections02:18

Fischer Projections

17.8K
Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...
17.8K
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
69.3K
Conformations of Butane02:20

Conformations of Butane

20.6K
Unlike ethane and propane that have only two major conformations, butane has more than two conformers. The staggered form of butane in which the bulky methyl groups on the two carbons are placed on opposite sides, that is, at a dihedral angle of 180°, is the lowest energy, most stable form — called the anti conformer. This conformation is stabilized due to the absence of steric repulsion between the largely spaced out methyl groups. The other two staggered conformations are...
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Updated: Mar 29, 2026

Spatial Separation of Molecular Conformers and Clusters
10:37

Spatial Separation of Molecular Conformers and Clusters

Published on: January 9, 2014

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1-Fluoropropane. Torsional Potential Surface.

Lionel Goodman1, Ronald R Sauers1

  • 1Department of Chemistry and Chemical Biology, Wright and Rieman Laboratories, Rutgers, the State University of New Jersey, New Brunswick, New Jersey 08903.

Journal of Chemical Theory and Computation
|December 4, 2015
PubMed
Summary

The gauche preference in 1-fluoropropane (FP) is primarily due to anti-C-H/C-F* hyperconjugation. This interaction, along with mode coupling involving CCC bending, significantly influences the conformational stability of FP.

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Molecular Modeling

Background:

  • Conformational analysis of small organic molecules is crucial for understanding chemical properties.
  • The gauche preference in 1-fluoropropane (FP) has been a subject of theoretical investigation.
  • Natural Bond Orbital (NBO) theory is a widely used method for analyzing electronic structure and bonding.

Purpose of the Study:

  • To elucidate the dominant electronic interactions governing the gauche preference of 1-fluoropropane.
  • To investigate the role of hyperconjugation and mode coupling in conformational preferences.
  • To assess the significance of Rydberg interactions in NBO analyses.

Main Methods:

  • Utilized Natural Bond Orbital (NBO) theory at the B3LYP/6-311++G(3df,2p) level of theory.
  • Performed systematic deletion of orbital interactions to isolate key electronic effects.
  • Employed Rydberg deletion calculations to evaluate the contribution of Rydberg orbitals.

Main Results:

  • Confirmed the anti-C-H/C-F* hyperconjugative interaction as the primary driver for the gauche preference in 1-fluoropropane.
  • Identified significant mode coupling between the FCCC torsion and CCC bending coordinates.
  • Demonstrated that Rydberg interactions can play a non-negligible role in NBO analysis.

Conclusions:

  • The gauche conformation of 1-fluoropropane is stabilized by a combination of anti-C-H/C-F* hyperconjugation and CCC bending-torsion mode coupling.
  • The anti-C-H/C-F* interaction is a key factor in this mode coupling.
  • The study highlights the importance of considering Rydberg interactions in theoretical chemical analyses.