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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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 overlap of p...
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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, respectively.
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

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

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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 Hückel’s rule or the 4n + 2 rule.
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

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 isolated benzene...
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.

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Related Experiment Video

Updated: May 25, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Non-aggregational aromatic oligoamide macrocycles.

Xiangxiang Wu1, Guoxing Liang, Gang Ji

  • 1College of Chemistry and College of Resources Science and Technology, Beijing Normal University, Beijing 100875, China.

Chemical Communications (Cambridge, England)
|January 19, 2012
PubMed
Summary
This summary is machine-generated.

New macrocycles with amide groups attached to cyclic aromatic oligoamides were synthesized. These macrocycles exhibit a rigid structure and guest-binding cavity without aggregation, despite modest formation yields.

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Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides
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Published on: November 21, 2013

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides
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Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides

Published on: November 21, 2013

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Cyclic aromatic oligoamides are known for their rigid backbones and defined cavities.
  • Modifying these structures can alter their properties and potential applications.

Purpose of the Study:

  • To synthesize novel macrocycles by functionalizing cyclic aromatic oligoamides.
  • To investigate the impact of peripheral amide groups on macrocycle behavior, aggregation, and guest-binding properties.

Main Methods:

  • Synthesis of novel macrocycles (2) through the attachment of peripheral amide groups to cyclic aromatic oligoamides (1).
  • Characterization of the resulting macrocycles to assess structural integrity and properties.

Main Results:

  • The new macrocycles (2) possess a rigid backbone and a defined internal cavity suitable for guest binding.
  • These macrocycles demonstrated no tendency to aggregate in solution.
  • The formation yields for the new macrocycles were modest.

Conclusions:

  • Peripheral amide functionalization is a viable strategy to create novel macrocyclic structures from oligoamides.
  • The synthesized macrocycles maintain key structural features like rigidity and a binding cavity while exhibiting altered aggregation behavior.