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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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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.
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Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
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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...
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Frost Circles for Different Conjugated Systems01:18

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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.
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In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
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Tricyclic 1,4-Diphosphinines: Local vs. Global Aromaticity.

Tim Kalisch1, Philipp C Brehm1, Rainer Streubel1

  • 1Institut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, 53121, Bonn, Germany) E-mail: E-mai.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|July 10, 2024
PubMed
Summary

This study explored the aromaticity of 1,4-diphosphinines using computational methods. Aromatic heterocycles enhance global aromaticity, while sulfur content and charge significantly influence ring currents.

Keywords:
AromaticityDiphosphinineHeterocyclic carbenesNICSTTF

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Aromaticity Studies

Background:

  • Tricyclic 1,4-diphosphinines are a novel class of phosphorus-containing heterocycles.
  • Understanding their aromatic properties is crucial for predicting their chemical behavior and potential applications.

Purpose of the Study:

  • To investigate the aromaticity of tricyclic 1,4-diphosphinines and related systems.
  • To evaluate the influence of fused rings and functional groups on aromatic properties.
  • To compare the aromaticity of 1,4-diphosphinines with benzene and pyrazine derivatives.

Main Methods:

  • Density Functional Theory (DFT) calculations, specifically 1D and 2D (Sigma only model) were employed.
  • Analysis focused on ring currents and global aromaticity metrics.
  • Comparison with established benzene and pyrazine systems was performed.

Main Results:

  • Non-aromatic heterocycles have a minor effect on local ring currents, while aromatic heterocycles induce global aromaticity.
  • Increased sulfur content in adjacent rings diminishes the central ring current.
  • 1,4-diphosphinine systems exhibit aromaticity more akin to benzene than pyrazine derivatives.
  • Charged systems, specifically the tetracation of bis(TTF)-fused 1,4-diphosphinines, show significant global aromaticity.

Conclusions:

  • The aromatic character of 1,4-diphosphinines is modulated by fused heterocyclic rings and sulfur content.
  • Aromaticity in these systems is strongly influenced by the presence and nature of adjacent rings and the overall charge state.
  • Charged 1,4-diphosphinines can achieve significant global aromaticity, comparable to other known aromatic heterocycles.