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Related Concept Videos

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

Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes

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 petroleum gas (LPG), fuel oil, gasoline, diesel fuel, and...
Mass Spectrometry: Cycloalkane Fragmentation01:05

Mass Spectrometry: Cycloalkane Fragmentation

In mass spectrometry, cycloalkanes exhibit distinct fragmentation patterns due to the inherent stability of their molecular ions compared to linear or branched alkanes. The ring structure of cycloalkanes provides additional stability to the molecular ions, often resulting in prominent ion peaks in the mass spectrum.
For example, cyclohexane molecular ions have a mass-to-charge ratio (m/z) of 84, which tends to produce a stronger signal than linear alkanes like hexane. This stability comes from...
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...
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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In Vitro Method to Control Concentrations of Halogenated Gases in Cultured Alveolar Epithelial Cells
04:56

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How strained are carbomeric-cycloalkanes?

Matthew D Wodrich1, Jérôme F Gonthier, Stephan N Steinmann

  • 1Laboratory for Computational Molecular Design, Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne, CH-1015 Lausanne, Switzerland.

The Journal of Physical Chemistry. A
|May 22, 2010
PubMed
Summary
This summary is machine-generated.

Ring strain energies in carbomeric-cycloalkanes were calculated using novel homodesmotic reactions. Adding acetylene units reduces strain, with near-zero strain observed in larger rings like cyclopentanes and cyclohexanes.

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Area of Science:

  • Computational chemistry
  • Organic chemistry
  • Physical chemistry

Background:

  • Carbomeric-cycloalkanes incorporate acetylene units into cyclic alkane structures.
  • Accurate assessment of ring strain in these molecules is crucial for understanding their stability and reactivity.
  • Existing methods using isodesmic and homodesmotic equations have limitations in balancing stereoelectronic effects.

Purpose of the Study:

  • To develop and apply a reliable method for calculating ring strain energies in carbomeric-cycloalkanes.
  • To investigate the influence of acetylene units and ring size on strain energy.
  • To validate computational results using an increment/additivity approach.

Main Methods:

  • Utilized a series of specifically designed homodesmotic reactions to balance stereoelectronic effects.
  • Calculated ring strain energies based on the proposed chemical equations.
  • Employed an increment/additivity approach to validate the computed strain values.

Main Results:

  • A novel set of homodesmotic reactions accurately quantifies ring strain by balancing all stereoelectronic effects.
  • Ring strain energy decreases with the addition of acetylene units.
  • Destabilization from bending acetylene bond angles diminishes in larger rings, resulting in near-zero strain for carbomeric-cyclopentanes and -cyclohexanes.

Conclusions:

  • The proposed homodesmotic reaction set provides an accurate method for determining ring strain in carbomeric-cycloalkanes.
  • The incorporation of acetylene units leads to a reduction in ring strain, particularly in larger ring systems.
  • Carbomeric-cyclopentanes and -cyclohexanes exhibit minimal ring strain, suggesting enhanced stability.