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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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

Criteria for Aromaticity and the Hückel 4n + 2 Rule

12.7K
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 +...
12.7K
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

13.4K
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...
13.4K
NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

6.2K
Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.
6.2K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.3K
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,...
5.3K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.6K
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.
3.6K

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Updated: Jan 14, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Neutral Aromatic 2,3-Diboranaphthalenes.

Taisong Zhao1, Yuyang Dai1, Ping Cui1

  • 1School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China.

Journal of the American Chemical Society
|October 24, 2025
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel neutral diboron naphthalene molecules, the first of their kind. These unique boron aromatic compounds exhibit diverse reactivity and expand the possibilities for main-group aromatic systems.

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Area of Science:

  • Organic Chemistry
  • Organoboron Chemistry
  • Aromatic Systems

Background:

  • Aromatic frameworks incorporating isosteric boron units offer unique electronic properties.
  • Naphthalene analogues with boron present opportunities for novel chemical reactivity.

Purpose of the Study:

  • To synthesize and characterize 2,3-diboranaphthalenes, the first neutral diboron analogues of naphthalene.
  • To explore the electronic structure, aromaticity, and reactivity of these novel boron aromatic systems.

Main Methods:

  • Synthesis of 2,3-diboranaphthalenes (compounds 2 and 4).
  • Characterization of their electronic properties and aromaticity.
  • Investigation of reactivity through complexation with group 6 metals and reactions with CO2, electrophiles, and selenium.

Main Results:

  • Successful synthesis of neutral 2,3-diboranaphthalenes featuring an o-diborabenzene core.
  • Demonstration of pronounced aromaticity and electron-rich character of the scaffold.
  • Symmetrical compound 2 formed metal complexes and underwent cycloaddition with CO2.
  • Unsymmetrical compound 4 exhibited electrophile-induced ring contraction and oxidative skeletal editing with selenium.

Conclusions:

  • 2,3-diboranaphthalenes represent a new class of neutral boron aromatics.
  • These compounds possess diverse reactivity, including ligand behavior and skeletal transformations.
  • The findings broaden the scope of main-group aromatic systems and their potential applications.