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Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
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Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

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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...
4.6K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

8.1K
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
8.1K
Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

3.1K
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...
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Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.8K
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...
3.8K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K

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Meta-Substituted Asymmetric Azobenzenes: Insights into Structure-Property Relationship.

Anna Laura Sanna1, Tatiana Pachova2, Alessandra Catellani3

  • 1Department of Chemical and Geological Sciences, Università degli Studi di Cagliari, SS 554, Bivio per Sestu, 09042 Cagliari, Italy.

Molecules (Basel, Switzerland)
|May 11, 2024
PubMed
Summary
This summary is machine-generated.

This study explores how adding electron-directing groups to methoxyphenylazobenzene affects its properties. Electron-withdrawing groups significantly alter spectra and slow down thermal relaxation, offering insights into structure-property relationships.

Keywords:
asymmetric functionalizationazobenzenemeta-substitutionmolecular switchstructure–property relationship

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Computational Chemistry

Background:

  • Azobenzenes are photo-switchable molecules with applications in materials science.
  • The position and nature of substituents significantly impact azobenzene properties.
  • Understanding structure-property relationships is crucial for designing novel photo-responsive materials.

Purpose of the Study:

  • To investigate the effect of meta-positioned electron-directing groups on methoxyphenylazobenzene.
  • To analyze the influence of electron-withdrawing and electron-donating groups on spectral and thermal properties.
  • To elucidate the structure-property relationships in meta-substituted asymmetrical phenolazobenzenes.

Main Methods:

  • Synthesis and spectroscopic analysis (UV-Vis) of meta-functionalized azobenzenes.
  • Investigation of thermal isomerization kinetics (Z to E relaxation).
  • Computational modeling (e.g., DFT) to understand electronic structure.

Main Results:

  • Electron-withdrawing groups caused significant changes in absorption spectra for both E and Z isomers.
  • Electron-donating groups induced more subtle spectral modifications.
  • Thermal relaxation from Z to E isomer was approximately twice as long for electron-withdrawing functionalized azobenzenes.
  • Computational analysis provided theoretical support for experimental observations.

Conclusions:

  • Meta-substitution with electron-directing groups profoundly impacts azobenzene photophysics.
  • Electron-withdrawing groups enhance spectral shifts and retard thermal relaxation.
  • The study provides valuable insights into the structure-property correlations of meta-substituted asymmetrical phenolazobenzenes.