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

¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.4K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
2.4K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.5K
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...
3.5K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.5K
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...
3.5K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.4K
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,...
4.4K
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 Hückel’s rule or...
10.6K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.3K
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.
3.3K

You might also read

Related Articles

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

Sort by
Same author

DUSP1 is a Key Driver of Disease Persistence and Potential Therapeutic Target in Hairy Cell Leukemia.

Blood advances·2026
Same author

Evaluating Molecular Docking Programs for RNA-Targeted Ligand Screening: Influence of Binding Modes and Ligand Types.

Journal of chemical information and modeling·2026
Same author

Dengue Virus Capsid Protein Interaction With Nucleic Acids.

BioFactors (Oxford, England)·2026
Same author

Engineering of acidic pH-responsive anti-CD3 binding antibodies.

mAbs·2026
Same author

Quantifying Spatially Resolved Hydration Thermodynamics Using Grid Inhomogeneous Solvation Theory [Article v1.0].

Living journal of computational molecular science·2026
Same author

Smooth-to-rough morphotype switching, a mechanism of phage resistance in <i><i>Mycobacterium</i> abscessus</i>.

Proceedings of the National Academy of Sciences of the United States of America·2026

Related Experiment Video

Updated: Apr 30, 2026

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
05:51

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method

Published on: July 19, 2019

5.8K

Heteroaromatic π-stacking energy landscapes.

Roland G Huber1, Michael A Margreiter, Julian E Fuchs

  • 1Institute of General, Inorganic and Theoretical Chemistry, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck , CCB - Center for Chemistry and Biomedicine, Innrain 80/82, A-6020 Innsbruck, Austria.

Journal of Chemical Information and Modeling
|April 30, 2014
PubMed
Summary

This study reveals that dispersion and electrostatic forces significantly influence pi-stacking interactions between aromatic heterocycles and benzene. Understanding these forces aids in optimizing molecular stacking for drug design.

More Related Videos

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

9.7K
Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

6.6K

Related Experiment Videos

Last Updated: Apr 30, 2026

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
05:51

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method

Published on: July 19, 2019

5.8K
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

9.7K
Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

6.6K

Area of Science:

  • Computational Chemistry
  • Molecular Modeling
  • Drug Discovery

Background:

  • Aromatic heterocycles are crucial in medicinal chemistry.
  • Understanding non-covalent interactions like pi-stacking is vital for drug design.
  • Accurate computational methods are needed to model these interactions.

Purpose of the Study:

  • To investigate pi-stacking interactions between aromatic heterocycles and benzene.
  • To quantify the contributions of dispersion and electrostatic forces.
  • To identify geometric preferences and interaction energies for drug-like molecules.

Main Methods:

  • Dispersion-corrected density functional theory (DFT) was employed.
  • Extensive potential energy surfaces were calculated for parallel-displaced geometries.
  • 13 common 5- and 6-membered aromatic heterocycles were studied.

Main Results:

  • Dispersion forces significantly contribute to the total interaction energy.
  • Electrostatic interactions play a key role in determining orientational preferences.
  • Minimum interaction energies and geometric preferences were determined for various heterocycles.

Conclusions:

  • The study provides detailed energy landscapes for heteroaromatic stacking.
  • Results can guide lead optimization by improving stacking interactions.
  • This work aids structure-based drug design through ring replacement strategies.