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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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

Criteria for Aromaticity and the Hückel 4n + 2 Rule

10.6K
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...
10.6K
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

10.8K
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...
10.8K
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
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.7K
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.
2.7K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.2K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Emerging frontiers in aromaticity.

Miquel Solà1, Israel Fernández2, Gabriel Merino3

  • 1Institut de Química Computacional i Catàlisi and Department de Química, Universitat de Girona C/ M. Aurèlia Capmany, 69 Girona 17003 Catalonia Spain miquel.sola@udg.edu.

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This collection explores aromaticity, a key chemical concept, highlighting recent advances across organic, inorganic, and materials chemistry. Discover the evolving significance and dynamic research in this fascinating field.

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Area of Science:

  • Chemistry, specifically focusing on aromaticity and its interdisciplinary applications.

Background:

  • Aromaticity, a foundational concept in chemistry for nearly two centuries, has evolved significantly.
  • This themed collection reviews recent advancements in aromaticity research published between 2021 and the present.

Discussion:

  • The concept of aromaticity extends beyond traditional organic chemistry.
  • Its influence is increasingly recognized in inorganic chemistry, organometallic chemistry, and materials science.

Key Insights:

  • The collection showcases thirty recent manuscripts from Chemical Science, illustrating the dynamic nature of current research.
  • It provides a comprehensive overview of the latest developments and applications of aromaticity.

Outlook:

  • Aromaticity continues to be a vibrant area of chemical research with broad implications.
  • Future research is expected to further explore its role in diverse chemical disciplines and material properties.