Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.4K
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...
4.4K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.4K
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...
4.4K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

6.1K
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,...
6.1K
Cycloalkanes02:28

Cycloalkanes

18.2K
Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
18.2K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

4.3K
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.
4.3K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

15.2K
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 +...
15.2K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Strain-Relief-Driven Rearrangement of [2.2]Paracyclophane Derivatives in the Synthesis of Biarylophanes.

Organic letters·2025
Same author

Discovery of AZD8421: A Potent CDK2 Inhibitor with Selectivity Against Other CDK Family Members and the Human Kinome.

Journal of medicinal chemistry·2025
Same author

Discovery and Optimization of Pyrazine Carboxamide AZ3246, a Selective HPK1 Inhibitor.

Journal of medicinal chemistry·2025
Same author

Discovery of 6-Fluoro-5-{4-[(5-fluoro-2-methyl-3-oxo-3,4-dihydroquinoxalin-6-yl)methyl]piperazin-1-yl}-<i>N</i>-methylpyridine-2-carboxamide (AZD9574): A CNS-Penetrant, PARP1-Selective Inhibitor.

Journal of medicinal chemistry·2024
Same author

Long-range Through-space Charge Transfer in a pH-responsive Mixed Cyclophane of Pyridine and Teropyrene.

Chemistry (Weinheim an der Bergstrasse, Germany)·2023
Same author

Glycine in a basket: protonated complexes of 1,1,<i>n</i>,<i>n</i>-tetramethyl[<i>n</i>](2,11)teropyrenophane (<i>n</i> = 7, 8, 9) with glycine in the gas-phase.

Physical chemistry chemical physics : PCCP·2023

Related Experiment Video

Updated: Apr 11, 2026

Characterization, Quantification and Compound-specific Isotopic Analysis of Pyrogenic Carbon Using Benzene Polycarboxylic Acids BPCA
08:12

Characterization, Quantification and Compound-specific Isotopic Analysis of Pyrogenic Carbon Using Benzene Polycarboxylic Acids BPCA

Published on: May 16, 2016

16.3K

Cyclophanes containing large polycyclic aromatic hydrocarbons.

Parisa Ghods Ghasemabadi1, Tieguang Yao, Graham J Bodwell

  • 1Chemistry Department, Memorial University, St. John's, NL, CanadaA1B 3X7. gbodwell@mun.ca.

Chemical Society Reviews
|May 30, 2015
PubMed
Summary

This review highlights cyclophanes with large polycyclic aromatic hydrocarbons (PAHs), detailing their synthesis and observed behaviors. These compounds showcase significant structural diversity and unique chemical properties.

More Related Videos

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.8K
Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

12.2K

Related Experiment Videos

Last Updated: Apr 11, 2026

Characterization, Quantification and Compound-specific Isotopic Analysis of Pyrogenic Carbon Using Benzene Polycarboxylic Acids BPCA
08:12

Characterization, Quantification and Compound-specific Isotopic Analysis of Pyrogenic Carbon Using Benzene Polycarboxylic Acids BPCA

Published on: May 16, 2016

16.3K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.8K
Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

12.2K

Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Cyclophanes are a well-established class of compounds, known for their structural diversity and interesting properties.
  • Research has primarily focused on cyclophanes with smaller aromatic systems.
  • Large polycyclic aromatic systems (≥4 rings) are less common in cyclophane chemistry.

Purpose of the Study:

  • To review cyclophanes incorporating large polycyclic aromatic systems (≥4 rings).
  • To illuminate the synthetic chemistry employed to create these complex structures.
  • To discuss the insights gained from studying their unique behaviors.

Main Methods:

  • Classification of general synthetic approaches for cyclophanes.
  • Detailed consideration of cyclophane anatomy.
  • Systematic review of cyclophanes based on eleven different PAHs.

Main Results:

  • Focus on cyclophanes containing large PAHs, from pyrene (C16) to hexabenzocoronene (C42).
  • Demonstration of synthetic strategies for incorporating large PAHs into cyclophane frameworks.
  • Highlighting the structural diversity and chemical properties of these advanced cyclophanes.

Conclusions:

  • Large polycyclic aromatic systems in cyclophanes represent a specialized but important area of research.
  • The synthesis and study of these compounds offer valuable insights into supramolecular chemistry.
  • Continued exploration promises further discoveries in structural complexity and functional properties.