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Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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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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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
2.9K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

11.2K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
11.2K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.0K
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...
3.0K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.9K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
2.9K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

13.1K
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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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Mechanical Strain-Controlled Aromaticity in Cyclo[n]Carbons.

O A Stasyuk1, C Curutchet2,3, A J Stasyuk2,3,4

  • 1Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, C/ Maria Aurèlia Capmany 69, Girona, Catalonia, 17003, Spain.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 25, 2025
PubMed
Summary
This summary is machine-generated.

Mechanical strain impacts cyclocarbon aromaticity. Radial contraction enhances electronic delocalization, transforming C18 into a highly aromatic system, offering a strategy for stable cyclocarbon design.

Keywords:
NICSaromaticitycyclo[n]carbonsmechanical strainradial contractionuniaxial tension

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Area of Science:

  • Computational chemistry
  • Materials science
  • Organic chemistry

Background:

  • Cyclocarbons exhibit unique electronic and mechanical properties.
  • Their high reactivity poses challenges for experimental study and application.

Purpose of the Study:

  • To investigate the effect of mechanical strain on the aromaticity of C16 and C18 cyclocarbons.
  • To explore strategies for enhancing cyclocarbon stability through mechanical manipulation.

Main Methods:

  • Molecular modeling was employed to simulate mechanical strain.
  • Aromaticity was assessed using magnetic (NICS, GIMIC) and electronic (π-EDDB, AV1245) indices.

Main Results:

  • Uniaxial tension slightly decreased aromaticity in both C16 and C18.
  • Radial expansion led to a significant loss of aromaticity.
  • Radial contraction enhanced electronic delocalization, particularly in C18.

Conclusions:

  • Radial contraction is a viable strategy to increase cyclocarbon aromaticity and stability.
  • An 8% radial contraction of C18 resulted in a highly aromatic system with equalized bond lengths.
  • This finding provides a pathway for designing stable, strained cyclocarbon architectures.