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Related Concept Videos

Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

19.7K
The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
19.7K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

16.3K
Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
16.3K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

16.1K
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.
For example, in...
16.1K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

11.2K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
11.2K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

15.4K
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...
15.4K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.3K
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
1.3K

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Conformational impact of structural modifications in 2-fluorocyclohexanone.

Francisco A Martins1, Josué M Silla1, Matheus P Freitas1

  • 1Department of Chemistry, Federal University of Lavras, 37200-000, Lavras, MG, Brazil.

Beilstein Journal of Organic Chemistry
|September 15, 2017
PubMed
Summary

Structural modifications in 2-fluorocyclohexanone were studied to understand conformational preferences. Classical effects, not the gauche effect, were found to govern the equilibrium between axial and equatorial conformers.

Keywords:
2-fluorocyclohexanoneclassical effectsconformational analysishyperconjugation

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Molecular Modeling

Background:

  • 2-Haloketones are versatile building blocks in materials science and medicinal chemistry.
  • Organic fluorine incorporation is crucial for designing high-performance molecules.
  • Molecular conformation significantly influences physicochemical and biological properties.

Purpose of the Study:

  • To investigate the intramolecular interactions influencing the conformational equilibrium of 2-fluorocyclohexanone.
  • To determine whether hyperconjugative or classical effects dominate conformational preferences in fluorinated cyclohexanones.

Main Methods:

  • Theoretical study of structural modifications in 2-fluorocyclohexanone.
  • Evaluation of hydrogen bonding, hyperconjugation, electrostatic, and steric effects.
  • Calculation of spectroscopic parameters (NMR chemical shifts and coupling constants).

Main Results:

  • The gauche effect from hyperconjugation does not favor the axial conformation in these organofluorine heterocycles.
  • Classical effects, such as steric and electrostatic interactions, are the primary drivers of conformational equilibrium.
  • Calculated spectroscopic parameters provide insights into stereochemistry and operative interactions.

Conclusions:

  • Conformational preferences in 2-fluorocyclohexanone derivatives are dictated by classical intermolecular forces.
  • Understanding these conformational dynamics is key for designing novel fluorinated organic molecules.
  • Computed NMR data can aid in the stereochemical elucidation of related compounds.