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

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

3.8K
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,...
3.8K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.8K
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...
2.8K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.7K
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...
2.7K
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
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

10.4K
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...
10.4K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

5.9K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
5.9K

You might also read

Related Articles

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

Sort by
Same author

Planar tetracoordinate oxygen stabilized within triel-chalcogen dicationic frameworks.

RSC advances·2026
Same author

FAM162A Is a Key Regulator of Mitochondrial Structure, Dynamics, and Bioenergetics, Driving Cellular Protection and Longevity.

Aging cell·2026
Same author

Connecting the Dots: Neurobiological Interplay Between Type 2 Diabetes and Alzheimer's Disease.

International journal of molecular sciences·2026
Same author

O©Li<sub>5</sub>F<sub>5</sub><sup>2-</sup>: A Global Minimum with a Planar Pentacoordinate Oxygen.

Inorganic chemistry·2026
Same author

Planar tetracoordinate nitrogen in main-group cationic clusters.

Physical chemistry chemical physics : PCCP·2026
Same author

From local to global or semilocal aromaticity: singlet-triplet switching in porphyrin tapes.

Chemical communications (Cambridge, England)·2026

Related Experiment Video

Updated: Jun 12, 2025

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

11.4K

Exploring aromatic rings with planar tetracoordinate group 13-15 atoms.

Dumer S Sacanamboy1,2, Pamela L Gamero-Begazo2, Kevin E Parco-Valencia2

  • 1Universidad Andres Bello, Facultad de Ciencias Exactas, Departamento de Ciencias Químicas, Centro de Química Teórica & Computacional (CQT&C), Avenida República 275, 8370146 Santiago de Chile, Chile. wtiznado@unab.cl.

Chemical Communications (Cambridge, England)
|September 27, 2024
PubMed
Summary

This study investigated planar tetracoordinate group 13-15 atoms in novel ring systems. True tetracoordination was only achieved in the C4H2NGe2+ system, revealing unique chemical bonding insights.

More Related Videos

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

8.4K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

6.9K

Related Experiment Videos

Last Updated: Jun 12, 2025

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

11.4K
Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

8.4K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

6.9K

Area of Science:

  • Inorganic Chemistry
  • Computational Chemistry
  • Materials Science

Background:

  • Exploring novel electronic structures and bonding in low-coordinate main group elements.
  • Investigating the stability and properties of cyclic systems incorporating group 13-15 elements.

Purpose of the Study:

  • To examine systems with planar tetracoordinate group 13-15 atoms (E) within pentagonal C4H2E rings.
  • To identify stable configurations and analyze chemical bonding in these novel structures.

Main Methods:

  • Detailed chemical bonding analysis using computational methods.
  • Systematic examination of eleven candidate structures.

Main Results:

  • Identified systems containing planar tetracoordinate group 13-15 atoms within pentagonal C4H2E rings.
  • Demonstrated that true tetracoordination is achieved exclusively in the C4H2NGe2+ system.
  • Provided insights into the electronic structure and bonding characteristics of these unique compounds.

Conclusions:

  • The C4H2NGe2+ system represents a rare example of true planar tetracoordination for group 13-15 elements.
  • Chemical bonding analysis is crucial for understanding the stability and properties of such exotic species.