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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

13.4K
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...
13.4K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

12.3K
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...
12.3K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

16.3K
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...
16.3K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

12.2K
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...
12.2K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

10.9K
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....
10.9K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.3K
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,...
9.3K

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Updated: May 6, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Local structure correlations in plastic cyclohexane--a reverse Monte Carlo study.

Nicholas P Funnell1, Martin T Dove, Andrew L Goodwin

  • 1EaStChem and Centre for Science at Extreme Conditions, University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, UK. Department of Chemistry, Inorganic Chemistry Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QR, UK.

Journal of Physics. Condensed Matter : an Institute of Physics Journal
|October 22, 2013
PubMed
Summary
This summary is machine-generated.

Investigating solid cyclohexane phases using neutron scattering reveals that the disordered structure of phase I exhibits local distortions similar to the ordered structure of phase II below 186 K.

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Area of Science:

  • Solid-state chemistry
  • Materials science
  • Crystallography

Background:

  • Cyclohexane exhibits distinct solid phases with varying molecular arrangements.
  • Understanding phase transitions is crucial for predicting material properties.

Purpose of the Study:

  • To investigate the structural properties of two solid phases of cyclohexane.
  • To analyze the local atomic configurations within these phases.

Main Methods:

  • Neutron total scattering experiments were performed on perdeuterated cyclohexane powder.
  • Temperatures ranged from 13 K to 266 K.
  • Reverse Monte Carlo (RMC) refinement was used to generate atomistic configurations.

Main Results:

  • Phase II (below 186 K) has an ordered monoclinic structure (C2/c).
  • Phase I (186–280 K) is a plastic crystalline phase with a face-centered cubic (Fm3m) structure, exhibiting rotational disorder.
  • RMC analysis revealed that instantaneous distortions in phase I resemble the average structure of phase II.

Conclusions:

  • The plastic phase I of cyclohexane contains local structural motifs similar to the ordered phase II.
  • This suggests a continuous relationship between the disordered and ordered states.