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Aromatic Hydrocarbon Cations: Structural Overview01:18

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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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According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
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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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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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UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the...
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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Angular ladder-type meta-phenylenes: synthesis and electronic structural analysis.

Anitha Boddeda1, Mohammad Mosharraf Hossain1, M Saeed Mirzaei2

  • 1Department of Chemistry, Marquette University, Milwaukee, WI 53201-1414, United States.

Organic Chemistry Frontiers : an International Journal of Organic Chemistry
|April 2, 2021
PubMed
Summary
This summary is machine-generated.

Researchers synthesized new ladder-type meta-phenylenes with keto or alkyl groups. Changing terminal groups impacts electronic properties and charge delocalization, showing a switch from class III to class II behavior in keto-bridged compounds.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Computational Chemistry

Background:

  • Ladder-type meta-phenylenes are complex organic molecules with unique electronic properties.
  • Tuning molecular structure, particularly terminal groups, can significantly alter electronic behavior.

Purpose of the Study:

  • To synthesize and characterize two new series of angular (all-syn) ladder-type meta-phenylenes (LMP).
  • To investigate the electronic and structural properties of angular keto (AKn) and angular alkyl (AAn) series.
  • To compare charge delocalization behavior between angular keto and alkyl series, and with linear analogues.

Main Methods:

  • Synthesis of angular keto (AKn) and angular alkyl (AAn) LMP series.
  • Electrochemical and spectroscopic (UV-Vis, emission) characterization.
  • Density Functional Theory (DFT) calculations for electronic structure and charge delocalization analysis.

Main Results:

  • Successful synthesis of AKn and AAn LMP series (n=3-8).
  • Experimental and DFT data show increased reduction potentials and LUMO energies for AKn compared to AAn due to extended π-systems.
  • AAn compounds exhibit Robin-Day class III charge stabilization, while AKn compounds switch from class III to class II.

Conclusions:

  • Terminal group modification (keto vs. alkyl) in angular ladder-type meta-phenylenes significantly influences electronic properties and charge stabilization mechanisms.
  • The charge delocalization mechanism in acceptor-π-acceptor systems is independent of molecular shape (angular vs. linear).