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Related Concept Videos

Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

11.1K
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday...
11.1K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.8K
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...
2.8K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

10.9K
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...
10.9K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
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...
2.9K
Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

11.3K
In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
11.3K
NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

4.8K
Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.
4.8K

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Related Experiment Video

Updated: Aug 2, 2025

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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Nonaromatic naphthocorroles.

Łukasz Kielesiński1, Francesco F Summa2, Jeanet Conradie3,4

  • 1Institute of Organic Chemistry of Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland. dtgryko@icho.edu.pl.

Chemical Communications (Cambridge, England)
|April 17, 2023
PubMed
Summary
This summary is machine-generated.

New naphthocorrole ligands combine corrole cavity size with porphyrin dianionic character. These nonaromatic compounds exhibit porphyrin-like spectra and are easily synthesized.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Photochemistry

Background:

  • Corroles and porphyrins are important macrocyclic ligands with distinct electronic and structural properties.
  • Tuning the properties of macrocyclic ligands is crucial for developing new functional materials.
  • Existing synthetic routes can be complex and limit accessibility.

Purpose of the Study:

  • To introduce novel naphthocorrole ligands.
  • To investigate the unique structural and electronic characteristics of these new ligands.
  • To establish a straightforward synthetic protocol for their preparation.

Main Methods:

  • Synthesis of naphthocorrole ligands via a simple, accessible protocol.
  • Spectroscopic characterization (UV-Vis, NMR) to confirm structure and properties.
  • Computational studies to understand electronic structure and spectral features.

Main Results:

  • Successful synthesis of new naphthocorrole ligands.
  • Demonstration of combined cavity size of corroles and dianionic character of porphyrins.
  • Observation of deceptively porphyrin-like optical spectra despite nonaromatic nature.
  • Establishment of a facile synthetic route.

Conclusions:

  • Naphthocorrole ligands represent a unique class of macrocycles.
  • These ligands offer a blend of corrole and porphyrin characteristics.
  • The simple synthetic protocol enhances their accessibility for further research and applications.