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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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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...
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Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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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...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.4K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
3.4K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

12.2K
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...
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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

16.1K
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...
16.1K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

10.8K
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....
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Accurate equilibrium structures for piperidine and cyclohexane.

Jean Demaison1, Norman C Craig, Peter Groner

  • 1Laboratoire de Physique des Lasers, Atomes et Molécules, Université de Lille 1 , 59655 Villeneuve d'Ascq Cedex, France.

The Journal of Physical Chemistry. A
|July 8, 2014
PubMed
Summary

This study refines microwave measurements for piperidine isotopologues, yielding highly accurate structural parameters for piperidine and cyclohexane. These precise molecular structures validate experimental rotational constants.

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Area of Science:

  • Molecular Spectroscopy
  • Quantum Chemistry
  • Computational Chemistry

Background:

  • Accurate molecular structures are crucial for understanding chemical properties and reactions.
  • Previous studies on piperidine and cyclohexane structures have limitations in precision.
  • Microwave spectroscopy provides high-resolution data for determining molecular geometry.

Purpose of the Study:

  • To perform extended and improved microwave measurements for piperidine isotopologues.
  • To determine highly accurate equilibrium structures of piperidine and cyclohexane.
  • To compare structural parameters between piperidine and cyclohexane and validate experimental data.

Main Methods:

  • Fitting new ground state rotational constants to microwave transitions.
  • Utilizing ab initio calculations for quartic centrifugal distortion constants and predicate geometric parameters.
  • Applying the mixed estimation method to fit equilibrium structures using experimental and theoretical data.
  • Correcting ground state rotational constants for vibration-rotation interactions and electronic contributions.

Main Results:

  • New ground state rotational constants for piperidine isotopologues were determined.
  • Equilibrium structures for piperidine and cyclohexane were fitted with high accuracy (0.001 Å and 0.2°).
  • Comparisons of bond parameters between equatorial piperidine and cyclohexane were made.
  • Structure determination was confirmed as an effective method for verifying experimental rotational constants.

Conclusions:

  • The study provides highly accurate equilibrium structures for piperidine and cyclohexane.
  • The results highlight the importance of ab initio calculations and advanced fitting methods in structural determination.
  • The findings contribute to a deeper understanding of molecular geometry and spectroscopic data validation.