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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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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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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.
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Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

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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?
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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Tribenzodecacyclene and hexabenzodecacyclene.

Xin Geng1, Joel T Mague1, Robert A Pascal1

  • 1Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, United States.

The Journal of Organic Chemistry
|April 9, 2015
PubMed
Summary

Researchers synthesized novel polycyclic aromatic hydrocarbons via titanium tetrachloride-catalyzed triple aldol condensations. The resulting molecular propellers, tribenzodecacyclene and hexabenzodecacyclene, exhibit distinct structural and stability properties.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Polycyclic aromatic hydrocarbons (PAHs) are crucial in materials science.
  • Molecular propellers offer unique three-dimensional structures with potential applications.
  • Developing efficient synthetic routes to complex PAHs remains a challenge.

Purpose of the Study:

  • To synthesize novel, highly conjugated, three-dimensional PAHs.
  • To investigate the structural and stability characteristics of these new compounds.
  • To explore the utility of TiCl4-catalyzed triple aldol condensations for constructing complex architectures.

Main Methods:

  • High-temperature triple aldol condensation reactions catalyzed by titanium tetrachloride (TiCl4).
  • Synthesis of tribenzodecacyclene (3) from aceanthrenone (5).
  • Synthesis of hexabenzodecacyclene (4) from acenaphthacenone (6).
  • Characterization using X-ray crystallography and Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Computational analysis using High-Density Functional Theory (HDFT).

Main Results:

  • Tribenzodecacyclene (3) was obtained in 16% yield as a stable, red crystalline solid.
  • Hexabenzodecacyclene (4) was obtained in 0.8% yield as an air- and light-sensitive blue-black solid.
  • X-ray crystallography revealed compound 3 to be a strongly pitched, C3-symmetric molecular propeller.
  • NMR spectra and HDFT calculations indicated compound 4 to be a D3-symmetric molecular propeller, highlighting its increased strain.

Conclusions:

  • TiCl4-catalyzed triple aldol condensation is a viable method for synthesizing complex, propeller-shaped PAHs.
  • The degree of strain significantly influences the stability and properties of these molecular architectures.
  • The synthesized compounds represent novel additions to the family of three-dimensional PAHs with potential for further investigation.