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Related Concept Videos

Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

11.0K
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...
11.0K
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
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
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

7.2K
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
7.2K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.1K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
6.1K
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

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Updated: Jul 28, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Aromaticity: Quo Vadis.

Gabriel Merino1, Miquel Solà2, Israel Fernández3

  • 1Departamento de Física Aplicada, Centro de Investigación y de Estudios Avanzados Unidad Mérida, km 6 Antigua Carretera a Progreso, Apdo. Postal 73, Cordemex 97310 Mérida Yucatán Mexico gmerino@cinvestav.mx.

Chemical Science
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Summary
This summary is machine-generated.

Aromaticity, a fundamental chemistry concept, lacks a unified definition despite its prevalence. This perspective explores the diverse theories and future directions for understanding aromaticity.

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Area of Science:

  • Chemistry
  • Theoretical Chemistry
  • Physical Chemistry

Background:

  • Aromaticity is a cornerstone concept in chemistry, fundamental to understanding molecular structure and reactivity.
  • Despite its widespread application, encompassing two-thirds of known compounds, a definitive, universally accepted definition of aromaticity remains elusive.
  • The proliferation of specific aromaticity types (e.g., sigma, pi, delta, spherical, Möbius, all-metal) highlights the complexity and ongoing debate surrounding the concept.

Purpose of the Study:

  • To critically examine the current state of the aromaticity concept within the chemical community.
  • To address the lack of consensus regarding the definition and scope of aromaticity.
  • To provide insights into the future trajectory and evolving understanding of aromaticity in chemistry.

Main Methods:

  • This perspective synthesizes existing literature and theoretical frameworks.
  • It analyzes the diverse criteria and models proposed for classifying aromaticity.
  • The study reflects on community discussions and trends in aromaticity research.

Main Results:

  • The study identifies a significant divergence in theoretical approaches to defining aromaticity.
  • It highlights the challenges posed by numerous specialized aromaticity descriptors.
  • The analysis reveals a community grappling with the fundamental nature and boundaries of aromaticity.

Conclusions:

  • The concept of aromaticity, while essential, is currently fragmented and lacks a unifying definition.
  • Further research and community consensus are needed to refine and consolidate the understanding of aromaticity.
  • The future of aromaticity likely involves integrating diverse theoretical models to capture its multifaceted nature.