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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.1K
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...
4.1K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.1K
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...
4.1K
Cycloalkanes02:28

Cycloalkanes

17.4K
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...
17.4K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

15.7K
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...
15.7K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

4.0K
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.
4.0K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

16.5K
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...
16.5K

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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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Pentagon-Embedded Cycloarylenes with Cylindrical Shapes.

Shunpei Hitosugi1,2, Sota Sato1,2, Taisuke Matsuno1,2

  • 1Department of Chemistry, The University of Tokyo, JST, ERATO, Isobe Degenerate π-Integration Project, Hongo 7-3-1, Bunkyo-ku, Tokyo, 113-0033, Japan.

Angewandte Chemie (International Ed. in English)
|June 14, 2017
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel cylinder-shaped molecules with non-hexagon bridges, embedding pentagons to study helical carbon structures. This work offers an experimental guide for exploring unusual graphitic carbon materials with cylindrical shapes.

Keywords:
conjugationmacrocyclesnanostructuresnanotubespentagons

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Carbon nanotubes feature cylinder-shaped graphitic networks, attracting interdisciplinary scientific interest.
  • The chemical synthesis of these curved, conjugated systems is a challenging yet significant area of chemistry.

Purpose of the Study:

  • To report the synthesis of cylinder-shaped molecules with non-hexagon bridges in their conjugated systems.
  • To investigate the stereoisomerism arising from helical carbon arrangements in molecules with embedded pentagons.

Main Methods:

  • Synthesis of novel cylinder-shaped molecules.
  • Structural analysis using Nuclear Magnetic Resonance (NMR) spectroscopy.
  • UV/Vis absorption spectroscopy.
  • Single-crystal X-ray diffraction.

Main Results:

  • Successfully synthesized discrete, cylinder-shaped molecules containing non-hexagon bridges.
  • Embedded multiple pentagon units within the conjugated systems.
  • Studied the stereoisomerism associated with helical carbon arrangements.
  • Obtained fundamental experimental data on curved, conjugated systems incorporating pentagons.

Conclusions:

  • This study presents the first experimental framework for synthesizing and analyzing curved graphitic carbon materials with non-hexagon units.
  • Provides insights into the structure and properties of helical carbon arrangements.
  • Paves the way for future research into anomalous graphitic carbon materials with cylindrical architectures.