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Related Concept Videos

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

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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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Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

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In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
16.6K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

14.9K
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 +...
14.9K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.3K
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...
4.3K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.4K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.4K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.3K
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...
4.3K

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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
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Electron Transmission through Aromatic Molecules.

Matthias Ernzerhof1, Hilke Bahmann1, Francois Goyer1

  • 1Département de Chimie, Université de Montréal, C.P. 6128 Succursale A, Montréal, Québec H3C 3J7, Canada.

Journal of Chemical Theory and Computation
|December 3, 2015
PubMed
Summary
This summary is machine-generated.

Ring currents, observed in nuclear magnetic resonance, also appear in molecular electronic devices. These currents can block electrons, creating observable magnetic moments in aromatic compounds.

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Area of Science:

  • Chemistry and Physics
  • Molecular Electronics
  • Quantum Phenomena

Background:

  • Aromatic compounds exhibit ring currents under external magnetic fields, detectable via nuclear magnetic resonance.
  • Molecular electronics utilizes molecules as conductors between metallic contacts for electron transport.

Purpose of the Study:

  • To investigate the presence and implications of ring currents in molecular electronic devices.
  • To explore the relationship between ring currents and electron transport in cyclic π-electron systems.

Main Methods:

  • Theoretical analysis of electron behavior in molecular electronic devices with cyclic π-electron systems.
  • Modeling of current generation and interference phenomena within these molecular systems.

Main Results:

  • Ring currents are identified in molecular electronic devices containing cyclic π-electron systems.
  • These circular currents arise from electron wave interference, potentially making the molecule impenetrable to electrons.
  • Large internal ring currents are stimulated even when external currents through the molecule are small.

Conclusions:

  • Internal ring currents in molecular electronic devices are a significant phenomenon.
  • These currents are predicted to generate experimentally observable magnetic moments.
  • The findings offer new insights into electron behavior and magnetic properties at the molecular level.