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

6.0K
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,...
6.0K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

14.5K
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 +...
14.5K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.2K
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...
4.2K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

4.1K
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.
4.1K
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.8K
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...
2.8K
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

12.5K
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
12.5K

You might also read

Related Articles

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

Sort by
Same author

Charging Pyracylene: Steering Aromaticity and Reactivity of [12]Annulene by Substitution.

Journal of the American Chemical Society·2026
Same author

Post-Modification of Tripyrenylenes to Enantiopure π-Extended D<sub>3</sub>-Symmetric Propellers.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Copper-Catalyzed Domino Strategy Construction of Fused Benzopyrroloazepinone through the Reaction of Allenyloximes and Arylboronic Acids.

Organic letters·2026
Same author

Palladium-Catalyzed Approach to Highly Luminescent <i>para</i>-Difuropyrazines.

The Journal of organic chemistry·2026
Same author

Synthesis of Soft Octahedral Nanoparticles through Supramolecular Self-Assembly of <i>C</i><sub>3</sub>-Symmetric Trinaphthylamine Trisamides.

Journal of the American Chemical Society·2026
Same author

Toward Larger Cyclo-9,10-Anthryleneparaphenylenes.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

Ethanol's Dual Role as a Mediator and Green Solvent in Photocatalytic Hydrogen Atom Transfer-Enabled Formal Ring-Closing Metathesis toward 2-Quinolinones.

The Journal of organic chemistry·2026
Same journal

Scalable Syntheses of Pseudouridine and <i>N</i><sup>1</sup>-Methylpseudouridine.

The Journal of organic chemistry·2026
Same journal

Silyl Radical Formation from Silanethiols via Sulfur Atom Transfer with Phosphinites.

The Journal of organic chemistry·2026
Same journal

Chiral Benzimidazole Manganese Catalysts for Asymmetric Transfer Hydrogenation of 3-Substituted 2<i>H</i>-1,4-Benzoxazines.

The Journal of organic chemistry·2026
Same journal

Thia-Michael Stapling of Allenamide-Incorporated α-Helical Antimicrobial Peptides.

The Journal of organic chemistry·2026
Same journal

Ru(II)-Catalyzed Hydrodefluorination of Monofluoroalkenes.

The Journal of organic chemistry·2026
See all related articles

Related Experiment Video

Updated: Mar 16, 2026

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

Bent N-Heteroarenes.

Sebastian Hahn1, Florian L Geyer1, Silke Koser1

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg , Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

The Journal of Organic Chemistry
|August 20, 2016
PubMed
Summary
This summary is machine-generated.

Researchers synthesized bent N-heteroarenes with potential applications in materials science. These compounds were efficiently produced using condensation reactions, with naphthoquinone derivatives showing higher yields.

More Related Videos

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.8K
Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

9.1K

Related Experiment Videos

Last Updated: Mar 16, 2026

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
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.8K
Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

9.1K

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • N-heteroarenes are important structural motifs in organic electronics and materials.
  • Bent N-heteroarenes offer unique electronic and optical properties due to their non-planar geometry.
  • Developing efficient synthetic routes to these molecules is crucial for further investigation.

Purpose of the Study:

  • To synthesize a series of bent N-heteroarenes.
  • To characterize their optical, electronic, and structural properties.
  • To explore the influence of different quinone precursors on synthesis yield.

Main Methods:

  • Condensation reactions between substituted aromatic ortho-diamines and 1,2-naphthoquinone or 1,2-anthraquinone.
  • Spectroscopic analysis (UV-Vis, fluorescence) to determine optical properties.
  • X-ray crystallography and computational methods for structural elucidation.
  • Yield optimization studies.

Main Results:

  • Successful synthesis of various bent N-heteroarenes.
  • Characterization of their photophysical and electronic behavior.
  • Demonstration that naphthoquinone-based products generally exhibit higher yields compared to anthraquinone-based products.
  • Yields ranging from 34% to 94% were achieved.

Conclusions:

  • The described condensation reactions provide an effective route to bent N-heteroarenes.
  • The choice of quinone precursor significantly impacts reaction efficiency.
  • These synthesized heteroarenes are promising candidates for applications in organic electronics and functional materials.