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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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

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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,...
5.9K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.1K
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...
4.1K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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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 +...
14.2K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

10.7K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Pyracylenes: Facile Synthetic Access and Continuous Face-To-Face Antiaromatic π‑Stacking.

Sheng-Yuan Cheng1, Jiun-Siang Juang1, Yu-Fang Huang1

  • 1Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei 10617, Taiwan.

JACS Au
|February 27, 2026
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Summary

Chemists can now synthesize pyracylenes, rare antiaromatic hydrocarbons, using a novel palladium-catalyzed method. These synthesized molecules form unique solid-state structures that reduce antiaromaticity and exhibit conductivity.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Pyracylene, a nonalternant hydrocarbon, is synthetically inaccessible due to its inherent antiaromaticity.
  • Polycyclic antiaromatic hydrocarbons are of interest for organic materials and π-stacked assemblies.

Purpose of the Study:

  • To develop a facile synthetic route to pyracylenes.
  • To investigate the structural, electronic, and solid-state properties of synthesized pyracylenes.

Main Methods:

  • Palladium-catalyzed ring contraction of diborinic acids for pyracylene synthesis.
  • Derivatization via bromination and palladium-catalyzed cross-coupling.
  • Characterization using UV-vis spectroscopy, cyclic voltammetry, DFT calculations, X-ray crystallography, and time-resolved microwave conductivity.

Main Results:

  • A facile synthesis of pyracylenes was achieved.
  • Three pyracylenes formed unprecedented continuous, face-to-face, antiaromatic π-stacks in the solid state.
  • NICS calculations indicated reduced antiaromaticity in the stacked structures, and conductivity measurements confirmed solid-state conductivity.

Conclusions:

  • The study presents a viable synthetic strategy for accessing pyracylenes.
  • The discovered solid-state packing in pyracylenes offers a method to mitigate antiaromaticity.
  • These findings open avenues for pyracylenes in organic materials applications.