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Related Concept Videos

Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

16.1K
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...
16.1K
Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes02:14

Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes

8.2K
The low reactivity in alkanes can be attributed to the non-polar nature of C–C and C–H σ bonds. Alkanes, therefore, were  initially termed as “paraffins,” derived from the Latin words: parum, meaning “too little,” and affinis, meaning “affinity.”
Alkanes undergo combustion in the presence of excess oxygen and high-temperature conditions to give carbon dioxide and water. A combustion reaction is the energy source in natural gas, liquified...
8.2K
Relative Stabilities of Alkenes01:59

Relative Stabilities of Alkenes

16.0K
The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene.  The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.
16.0K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

16.8K
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...
16.8K
Conformations of Ethane and Propane02:18

Conformations of Ethane and Propane

18.9K
In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered...
18.9K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

16.7K
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...
16.7K

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Measurement of the Rheology of Crude Oil in Equilibrium with CO2 at Reservoir Conditions
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Can Strained Hydrocarbons Be "Forced" To Be Stable?

Tim Stauch1, Benjamin Günther2, Andreas Dreuw1

  • 1Interdisciplinary Center for Scientific Computing , Im Neuenheimer Feld 205, 69120 Heidelberg, Germany.

The Journal of Physical Chemistry. A
|September 1, 2016
PubMed
Summary

Mechanical forces can stabilize strained cycloalkynes like cycloheptyne. Stronger forces, achieved by incorporating the molecule into strained macrocycles, are more effective than those from photoswitches for stabilizing these reactive hydrocarbons.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Chemical Physics

Background:

  • Strained hydrocarbons, particularly cycloalkynes, are highly reactive.
  • Reactivity includes isomerization, dimerization, and trimerization under standard conditions.
  • Stabilizing these molecules is crucial for synthetic applications.

Purpose of the Study:

  • To investigate the stabilization of angle-strained cycloalkynes using mechanical forces.
  • To quantify the energy distribution and stability changes in cycloheptyne under external force.
  • To compare the efficacy of different force-application methods.

Main Methods:

  • Computational JEDI (Judgement of Energy DIstribution) analysis.
  • Isodesmic and homodesmotic reactions for stability assessment.
  • Modeling the application of mechanical pulling forces via photoswitches and macrocyclic incorporation.

Main Results:

  • Cycloheptyne can be stabilized by external mechanical forces.
  • Forces generated by photoswitches are insufficient for significant stabilization.
  • Incorporating cycloheptyne into a second strained macrocycle provides a more effective stabilization method.

Conclusions:

  • Mechanical stabilization of strained cycloalkynes is feasible.
  • The magnitude of the applied force is critical for effective stabilization.
  • Macrocyclic incorporation offers a promising strategy for stabilizing highly strained cycloalkynes.