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Conformations of Cyclohexane

Conformations of Cyclohexane

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...

Chair Conformation of Cyclohexane

Chair Conformation of Cyclohexane

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...

Conformations of Cycloalkanes

Conformations of Cycloalkanes

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...

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

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...

Stability of Substituted Cyclohexanes

Stability of Substituted Cyclohexanes

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...

Conformations of Ethane and Propane

Conformations of Ethane and Propane

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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Related Experiment Video

Updated: Mar 21, 2026

Orientational Transition in a Liquid Crystal Triggered by the Thermodynamic Growth of Interfacial Wetting Sheets

Orientational Transition in a Liquid Crystal Triggered by the Thermodynamic Growth of Interfacial Wetting Sheets

Published on: May 15, 2017

Orientational relaxations in solid (1,1,2,2)tetrachloroethane.

P Tripathi¹, E Mitsari¹, M Romanini¹

¹Grup de Caracterització de Materials, Departament de Física i Enginyeria Nuclear, Universitat Politècnica de Catalunya, ETSEIB, Diagonal 647, 08028 Barcelona, Spain.

The Journal of Chemical Physics

|May 2, 2016

Summary

This summary is machine-generated.

Dielectric spectroscopy and molecular simulations reveal three distinct orientational dynamics in solid tetrachloroethane. A slow, cooperative motion linked to a glassy transition involves 180° molecular rotations.

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Area of Science:

Molecular Solid-State Physics
Dielectric Spectroscopy
Computational Chemistry

Background:

Understanding molecular dynamics in orientationally disordered solids is crucial for materials science.
Dielectric spectroscopy and molecular dynamics simulations are powerful tools for probing molecular motion.

Purpose of the Study:

To investigate the complex orientational dynamics in the solid phase of (1,1,2,2)tetrachloroethane.
To elucidate the nature of distinct dielectric loss features and their relationship to molecular motion.

Main Methods:

Utilizing dielectric spectroscopy to measure relaxation processes.
Employing molecular dynamic simulations to model and understand molecular behavior.

Main Results:

Observed three distinct dielectric loss features, each with temperature-dependent activation.
Identified a slow, cooperative 180° rotation around the molecular symmetry axis linked to a glassy transition at 156 K.
Characterized an intermediate Johari-Goldstein precursor relaxation and a fast single-molecule orientational fluctuation.
Determined a Kirkwood correlation factor indicating strong antiparallel dipole alignment during cooperative motion.

Conclusions:

The combined approach of dielectric spectroscopy and molecular simulations provides detailed insights into molecular solid dynamics.
Tetrachloroethane exhibits complex orientational dynamics, including cooperative and single-molecule motions.
Antiparallel alignment of molecular dipoles is significant during collective reorientation in this solid phase.