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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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.
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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.
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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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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.
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Conformations of Cyclohexane02:11

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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.
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Cycloparaphenylene Möbius trefoils.

Steven M Bachrach1, Henry S Rzepa

  • 1School of Science, Monmouth University, 400 Cedar Avenue, West Long Branch, NJ 07764, USA. sbachrac@monmouth.edu.

Chemical Communications (Cambridge, England)
|November 5, 2020
PubMed
Summary
This summary is machine-generated.

Density Functional Theory (DFT) computations reveal cycloparaphenylenes with three linking groups adopt two Möbius topologies. More stable C2 conformers exhibit a single half-twist (Lk=1), unlike D3 conformers with three half-twists (Lk=3).

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Area of Science:

  • Computational Chemistry
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Cycloparaphenylenes are molecular analogues of graphene fragments.
  • Möbius topologies in molecules are of interest due to their unique electronic and topological properties.
  • Understanding molecular conformations is crucial for predicting material properties.

Purpose of the Study:

  • To investigate the conformational preferences and topological properties of cycloparaphenylenes with three internal linking groups.
  • To explore the formation of Möbius topologies in these systems.
  • To correlate molecular structure with topological characteristics.

Main Methods:

  • Density Functional Theory (DFT) computations utilizing the ωB97X-D/6-31G(d) level of theory.
  • Analysis of molecular conformations and topological descriptors, specifically the linking number (Lk).
  • Systematic study of eight different cycloparaphenylene derivatives.

Main Results:

  • Two distinct conformations were identified for the studied cycloparaphenylenes.
  • The D3 conformers exhibit a linking number (Lk) of 3, corresponding to a trefoil knot with three half-twists.
  • The more stable C2 conformers display a single half-twist, resulting in a linking number (Lk) of 1, a simpler Möbius topology.

Conclusions:

  • Cycloparaphenylenes with three internal linking groups can adopt stable Möbius topologies.
  • Conformational stability is linked to the complexity of the topological structure.
  • These findings contribute to the understanding of topological isomerism in molecular systems.