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Five-Membered Heterocyclic Aromatic Compounds: Overview

Five-Membered Heterocyclic Aromatic Compounds: Overview

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, respectively.

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

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 overlap of p...

¹H NMR: Long-Range Coupling

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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 π orbitals.

π Molecular Orbitals of 1,3-Butadiene

π Molecular Orbitals of 1,3-Butadiene

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...

Hybridization of Atomic Orbitals II

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization

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Pyrene: hydrogenation, hydrogen evolution, and π-band model.

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Updated: May 11, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Polycyclic aromatic hydrocarbons: trends for bonding hydrogen.

Jakob Arendt Rasmussen¹

¹Interdisciplinary Nanoscience Center and Department of Physics and Astronomy, Ny Munkegade, Building 1520, Aarhus University, DK-8000 Aarhus C, Denmark. jar@inano.au.dk

The Journal of Physical Chemistry. A

|April 30, 2013

Summary

Hydrogenation of polycyclic aromatic hydrocarbons is key for electronics and hydrogen storage. This study reveals two-fold coordinated carbons are preferred binding sites, with distinct structural and electronic properties.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Area of Science:

Physical Chemistry
Materials Science
Astrochemistry

Background:

Hydrogenation of carbonaceous materials is crucial for applications in carbon-based electronics and hydrogen storage.
Understanding these reactions is also vital for astrochemistry, particularly the catalytic formation of molecular hydrogen in space.

Purpose of the Study:

To systematically investigate the hydrogenation of small closed-shell polycyclic aromatic hydrocarbons (PAHs).
To explore the binding energies and preferred binding sites on PAHs using computational methods.

Main Methods:

Density functional theory (DFT) calculations were employed.
The study analyzed the hydrogenation of PAHs up to four carbon hexagons, including linear acenes like pentacene, hexacene, and heptacene.

Main Results:

Binding energies for hydrogenation ranged from 0.43 to 2.70 eV.
Two-fold coordinated carbon atoms were identified as the preferred binding sites, with binding energies between 1.06 and 2.70 eV.
Three distinct binding motifs with unique structural and electronic fingerprints were characterized, explaining the observed binding site preferences.

Conclusions:

The study provides fundamental insights into the hydrogenation mechanisms of PAHs.
Identified preferred binding sites and their characteristics can guide the design of materials for electronics and hydrogen storage.
The findings contribute to understanding chemical processes in interstellar environments.