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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.4K
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...
3.4K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.3K
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...
3.3K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.4K
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.
3.4K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

12.2K
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 Hückel’s rule or the 4n +...
12.2K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

17.1K
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.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
17.1K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

13.5K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
13.5K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Radially Oriented [n]Cyclo-meta-phenylenes.

Edison Castro1, Saber Mirzaei1, Raúl Hernández Sánchez1

  • 1Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, United States.

Organic Letters
|December 17, 2020
PubMed
Summary

Researchers synthesized rare zigzag carbon nanotubes, described as radially oriented [n]cyclo-meta-phenylenes. This discovery introduces radial orbital distribution in novel zigzag nanorings.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Molecular compounds with zigzag carbon nanotube geometries are exceptionally rare.
  • Existing research has not fully explored zigzag nanostructures in carbon-based materials.

Purpose of the Study:

  • To synthesize and characterize novel carbon-based nanotubes with a zigzag geometry.
  • To extend the known family of tubularene compounds.
  • To investigate the emergence of radial orbital distribution in nanorings.

Main Methods:

  • Synthesis of radially oriented [n]cyclo-meta-phenylenes.
  • Characterization of the synthesized zigzag carbon nanotubes.
  • Incorporation of edge-sharing benzene rings into the tubularene's radial π-surface.

Main Results:

  • Successful synthesis and characterization of carbon-based nanotubes with zigzag geometry.
  • Demonstration of radially oriented [n]cyclo-meta-phenylenes as a new class of tubularenes.
  • Observation of the first step towards radial orbital distribution in zigzag nanorings.

Conclusions:

  • This study reports the first synthesis of zigzag carbon nanotubes.
  • The findings open new avenues for designing novel nanostructures with unique electronic properties.
  • The work represents a significant advancement in the field of carbon nanomaterials.