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Related Concept Videos

Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

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 annulenes. In...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...
Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the more strongly...
Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the ortho, meta, and para...

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Substituent effects on the aromatic edge-to-face interaction.

Felix Raoul Fischer1, W Bernd Schweizer, François Diederich

  • 1Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH-Hönggerberg, HCI, CH-8093 Zurich, Switzerland.

Chemical Communications (Cambridge, England)
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Summary

Substituent effects on molecular torsion balances were explained by analyzing changes in electrostatic interactions, exchange repulsion, and dispersion forces. These factors influence the overall interaction free enthalpy, impacting folding equilibrium.

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Area of Science:

  • Molecular chemistry
  • Physical chemistry
  • Computational chemistry

Background:

  • Molecular torsion balances are crucial for studying conformational preferences.
  • Understanding substituent effects is key to predicting molecular behavior.
  • Previous studies have explored various factors influencing molecular folding.

Purpose of the Study:

  • To rationalize substituent effects on the folding equilibrium of molecular torsion balances.
  • To investigate the contributions of electrostatic, exchange repulsion, and dispersive forces.
  • To provide a deeper understanding of non-covalent interactions in molecular systems.

Main Methods:

  • Computational chemistry methods were employed to model molecular systems.
  • Analysis of interaction free enthalpy was performed.
  • Decomposition of forces into electrostatic, exchange repulsion, and dispersion components.

Main Results:

  • Substituent effects significantly alter the folding equilibrium.
  • Electrostatic interactions, exchange repulsion, and dispersion forces were identified as key contributors.
  • The interplay of these forces dictates the overall stability of folded conformations.

Conclusions:

  • The folding equilibrium of molecular torsion balances is governed by a combination of electrostatic, exchange repulsion, and dispersive forces.
  • This study provides a framework for predicting and controlling molecular folding through substituent modification.
  • The findings have implications for the design of novel molecular architectures and materials.