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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

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...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Aromatic Hydrocarbon Cations: Structural Overview01:18

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...
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

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.
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

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...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Aromaticity in cyclic alkali clusters.

Snehadrinarayan Khatua1, Debesh R Roy, Patrick Bultinck

  • 1Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.

Physical Chemistry Chemical Physics : PCCP
|May 1, 2008
PubMed
Summary

Metal clusters of sodium and potassium (M6) exhibit aromatic properties, similar to organic polyacenes. These findings reveal new insights into inorganic aromaticity and cluster stability.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Area of Science:

  • Inorganic Chemistry
  • Computational Chemistry
  • Materials Science

Background:

  • Aromaticity is a fundamental concept in organic chemistry, typically associated with cyclic, planar molecules containing delocalized pi electrons.
  • The exploration of aromaticity in inorganic systems, particularly in metal clusters, is an emerging area of research.
  • Previous studies have investigated the electronic properties of metal clusters, but direct comparisons to organic aromaticity benchmarks are less common.

Purpose of the Study:

  • To investigate the aromatic character of hexagonal 1D sodium (Na6) and 2D potassium (K6) clusters.
  • To compare the aromaticity of these metal clusters with well-established organic polyacene analogues.
  • To understand the stability and reactivity patterns of these M6 rings.

Main Methods:

  • Utilizing Density Functional Theory (DFT) calculations to model the electronic structure of Na6 and K6 clusters.
  • Employing the Nucleus Independent Chemical Shift (NICS) method to quantify aromaticity.
  • Calculating multicenter bond indices (MCI) to assess electron delocalization and bonding characteristics.

Main Results:

  • DFT calculations confirm that the M6 (M = Na, K) rings exhibit aromatic characteristics.
  • NICS values for the Na6 and K6 rings are comparable to those of polyacene analogues, indicating significant electron delocalization.
  • MCI values further support the aromatic nature of these metal rings.
  • The stability and reactivity patterns of the M6 rings show trends similar to their organic counterparts.

Conclusions:

  • The M6 rings in the studied sodium and potassium clusters possess aromatic character.
  • This study extends the concept of aromaticity beyond traditional organic systems into inorganic metal clusters.
  • The findings suggest that inorganic clusters can mimic the electronic and chemical behavior of organic aromatic compounds, opening new avenues for materials design.