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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...

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...

Disubstituted Cyclohexanes: cis-trans Isomerism

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....

Mass Spectrometry: Cycloalkane Fragmentation

Mass Spectrometry: Cycloalkane Fragmentation

In mass spectrometry, cycloalkanes exhibit distinct fragmentation patterns due to the inherent stability of their molecular ions compared to linear or branched alkanes. The ring structure of cycloalkanes provides additional stability to the molecular ions, often resulting in prominent ion peaks in the mass spectrum.
For example, cyclohexane molecular ions have a mass-to-charge ratio (m/z) of 84, which tends to produce a stronger signal than linear alkanes like hexane. This stability comes from...

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Fully Autonomous Characterization and Data Collection from Crystals of Biological Macromolecules

Fully Autonomous Characterization and Data Collection from Crystals of Biological Macromolecules

Published on: March 22, 2019

Cyclo-hexane plastic phase I: single-crystal diffraction images and new structural model.

Sylvain Bernès¹, Sebastian Camargo¹

¹Instituto de Física Luis Rivera Terrazas, Benemérita Universidad Autónoma de Puebla, 18 Sur y San Claudio S/N, Puebla, Pue. 72570, Mexico.

|May 14, 2023

Summary

This summary is machine-generated.

This study determined the disordered molecular structure of plastic cyclohexane using a novel polyhedral modeling approach. This method successfully refined atomic positions, overcoming previous limitations in crystallographic analysis.

Keywords:

X-ray diffraction cyclohexane diffraction image disorder plastic crystals

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Area of Science:

Solid-state chemistry
Crystallography
Materials science

Background:

Previous studies by Kahn et al. (1973) failed to determine the atomic coordinates of plastic cyclohexane (polymorph I).
Direct determination of carbon atom positions is challenging due to inherent disorder in high-symmetry space groups of plastic materials.

Purpose of the Study:

To determine the molecular structure of plastic cyclohexane.
To overcome limitations in previous crystallographic analyses of disordered plastic phases.

Main Methods:

Utilized a polyhedral cluster model to describe the disorder of cyclohexane molecules.
Assumed disorder based on the rotation group 432 and analyzed reflections {111}, {200}, and {113} in the Fm3m space group.
Modeled the disordered cyclohexane molecule as a rhombic dodecahedron within an fcc Bravais lattice, with carbon atoms at the vertices.

Main Results:

The cyclohexane molecule was found to be disordered over 24 positions.
The polyhedral model successfully reduced the asymmetric unit to two carbon atoms on special positions.
An acceptable agreement was achieved between observed and calculated structure factors.

Conclusions:

The polyhedral cluster model is an effective tool for determining the molecular structure of disordered plastic materials like cyclohexane.
This approach provides a satisfactory solution for the crystallographic analysis of cyclohexane polymorph I.