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Related Concept Videos

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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,...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

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.
Cycloalkanes02:28

Cycloalkanes

Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
Stability of Substituted Cyclohexanes02:30

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...
Chair Conformation of Cyclohexane02:02

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 staggered...
Conformations of Cyclohexane02:11

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 tetrahedral value,...

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

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Published on: December 16, 2022

Polymorphism in cyclohexanol.

Richard M Ibberson1, Simon Parsons, David R Allan

  • 1ISIS Facility, STFC Rutherford Appleton Laboratory, Harwell Science and Innovation Campus, Didcot OX11 0QX, England. r.m.ibberson@rl.ac.uk

Acta Crystallographica. Section B, Structural Science
|September 19, 2008
PubMed
Summary
This summary is machine-generated.

This study reveals the crystal structures of cyclohexanol

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Area of Science:

  • Solid-state chemistry
  • Crystallography
  • Materials science

Background:

  • Cyclohexanol exhibits complex phase behavior, including plastic phase I and lower-temperature phases.
  • Understanding the molecular arrangements and hydrogen bonding in these phases is crucial for predicting material properties.

Purpose of the Study:

  • To determine the crystal structures and phase transitions of cyclohexanol phases II, III', and III.
  • To elucidate the molecular organization and hydrogen bonding motifs in these phases.
  • To reconcile structural findings with existing spectroscopic data.

Main Methods:

  • High-resolution neutron powder diffraction
  • Synchrotron X-ray powder diffraction
  • Single-crystal X-ray diffraction

Main Results:

  • Phase II crystallizes in a tetragonal structure with a hydrogen-bonded tetrameric ring motif.
  • Phases III' and III exhibit monoclinic structures with hydrogen-bonded molecular chains (threefold-helical and wave-like, respectively).
  • Cyclohexanol molecules adopt a chair conformation with equatorial hydroxyl groups in all studied phases, challenging some spectroscopic interpretations.

Conclusions:

  • The study provides detailed structural insights into cyclohexanol phases II, III', and III.
  • The findings clarify the hydrogen bonding patterns and molecular conformations in these solid phases.
  • Discrepancies with spectroscopic literature regarding hydroxyl group orientation are highlighted, suggesting further investigation.