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Related Concept Videos

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...
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.
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,...
Conformations of Cycloalkanes02:29

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 was based on the...
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,...

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Updated: Jun 15, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Substituent effects on dynamics at conical intersections: cyclopentadienes.

Oliver Schalk1, Andrey E Boguslavskiy, Albert Stolow

  • 1Steacie Institute for Molecular Sciences, National Research Council, Ottawa, Ontario K1A 0R6, Canada.

The Journal of Physical Chemistry. A
|March 3, 2010
PubMed
Summary

Substituent effects on conical intersection dynamics were studied using femtosecond spectroscopy. Increasing substituent inertia on the S(1) surface slows internal conversion, challenging simple radiationless transition models.

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Published on: March 20, 2017

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Area of Science:

  • Chemical Physics
  • Molecular Dynamics
  • Spectroscopy

Background:

  • Conical intersections are crucial in photochemistry, mediating ultrafast radiationless transitions.
  • Understanding substituent effects on these dynamics is key to controlling photochemical reactions.

Purpose of the Study:

  • To investigate how substituents on cyclopentadiene influence dynamics at conical intersections.
  • To explore the impact of substitution on excited state surfaces and internal conversion processes.

Main Methods:

  • Femtosecond time-resolved photoelectron spectroscopy was employed.
  • UV excitation was used to probe dynamics on the S(2) and S(1) electronic states.

Main Results:

  • Dynamics at the S(2)/S(1) conical intersection were insensitive to 5-position substitution.
  • Internal conversion on the S(1) surface slowed with increased substituent inertia at the 5-position.
  • Observed dynamics contradicted simple models predicting faster transitions with increased state density.

Conclusions:

  • Vibrational motions at conical intersections are critical and depend on specific modes.
  • Substituent inertia plays a significant role in slowing internal conversion dynamics.
  • A detailed dynamical picture is needed to fully understand radiationless transitions at conical intersections.