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Related Concept Videos

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
Constitutional Isomers of Alkanes02:18

Constitutional Isomers of Alkanes

Organic compounds of the same molecular formula can have different structural formulas called constitutional isomers, and the phenomenon is known as constitutional isomerism. Alkanes with four or more carbons showing multiple structures with the same molecular formula thereby exhibit constitutional isomerism.
The linear isomer of an alkane is prefixed by the term “n”; hence a linear isomer of pentane is known as n-pentane. Based on the type of branching, some of the branched isomers are given...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Structural Isomerism02:34

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...

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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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Patterns of ring current in coronene isomers.

Alexandru T Balaban, David E Bean, Patrick W Fowler

    Acta Chimica Slovenica
    |September 25, 2013
    PubMed
    Summary
    This summary is machine-generated.

    The ipsocentric pseudo-p model predicts aromaticity in coronene isomers. These molecules exhibit strong ring currents, meeting magnetic criteria for aromaticity.

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    Published on: July 27, 2022

    Area of Science:

    • Computational chemistry
    • Organic chemistry
    • Theoretical chemistry

    Background:

    • Aromaticity is a key concept in organic chemistry, influencing molecular properties and reactivity.
    • Coronene and its isomers represent complex polycyclic aromatic hydrocarbons with unique electronic structures.
    • Understanding the magnetic properties of these systems is crucial for predicting their behavior.

    Purpose of the Study:

    • To predict induced current density maps for coronene isomers using the ipsocentric pseudo-p model.
    • To investigate the aromaticity of coronene isomers based on their magnetic response.
    • To explore the relationship between molecular structure and aromaticity in complex polycyclic systems.

    Main Methods:

    • Utilizing the ipsocentric pseudo-p model for computational predictions.
    • Generating maps of induced current density.
    • Analyzing perimeter ring currents in various coronene isomers.

    Main Results:

    • The ipsocentric pseudo-p model successfully predicted current density maps for coronene isomers.
    • All investigated coronene isomers demonstrated strong diatropic perimeter ring currents.
    • These findings indicate conformity to the magnetic criterion of aromaticity for all isomers.

    Conclusions:

    • Coronene isomers, regardless of the surrounding ring sizes (5, 6, and 7-membered), exhibit robust aromatic character.
    • The magnetic criterion of aromaticity is consistently met by these isomers.
    • The ipsocentric pseudo-p model serves as a reliable tool for assessing aromaticity in complex polycyclic systems.