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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.3K
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...
4.3K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.3K
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...
4.3K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

17.3K
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...
17.3K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

4.2K
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.
4.2K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

10.0K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
10.0K
Carbocations02:10

Carbocations

14.8K
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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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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Aromatic stabilization of functionalized corannulene cations.

Jingbai Li1, Andrey Yu Rogachev1

  • 1Department of Chemistry, Illinois Institute of Technology, Chicago, IL 60616, USA. andrey.rogachev@gmail.com andrey.rogachev@iit.edu.

Physical Chemistry Chemical Physics : PCCP
|January 23, 2016
PubMed
Summary

This study investigates aromaticity in methyl-functionalized corannulene cations. The hub-isomer exhibits exceptional stability due to preserved aromaticity, unlike rim- and spoke-isomers.

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Area of Science:

  • Organic Chemistry
  • Theoretical Chemistry
  • Computational Chemistry

Background:

  • Corannulene is a unique polycyclic aromatic hydrocarbon with a bowl-shaped structure.
  • Functionalization of corannulene can significantly alter its electronic properties and stability.
  • Understanding aromaticity in functionalized corannulene cations is crucial for designing novel materials.

Purpose of the Study:

  • To conduct the first comprehensive theoretical investigation of aromaticity in functionalized corannulene cations.
  • To compare the aromaticity and stability of different isomers: hub-, rim-, and spoke-methylated corannulene cations.
  • To elucidate the structural and electronic factors governing the stability of these systems.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed.
  • Aromaticity was assessed using various descriptors: HOMA, PDI, FLU, and NICS.
  • Analysis of electron delocalization and conjugation was performed using the ACID tool.
  • Calculation and comparison of (1)H and (13)C chemical shifts with experimental data.

Main Results:

  • The hub-isomer ([CH3-hub-C20H10](+)) demonstrated exceptional stability.
  • Conservation of aromaticity in the 6-membered rings and vanishing anti-aromaticity in the central 5-membered ring contributed to the hub-isomer's stability.
  • Functionalization at the rim or spoke positions led to a significant loss of aromaticity in the 6-membered rings.
  • The rim- and spoke-isomers exhibited reduced stability compared to the hub-isomer, with retained anti-aromatic character in the central ring.

Conclusions:

  • The hub-isomer of methyl-functionalized corannulene cation is highly stable due to preserved aromaticity.
  • Rim- and spoke-functionalization drastically reduces aromaticity and stability.
  • Theoretical insights provide a basis for understanding structure-property relationships in functionalized corannulenes.