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Related Concept Videos

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

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.8K
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...
4.8K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.8K
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,...
2.8K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.1K
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...
5.1K
Nucleophilic Substitution Reactions02:34

Nucleophilic Substitution Reactions

19.7K
Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
19.7K
Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

14.3K
In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
14.3K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

7.5K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
7.5K

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Fabricating Complex Culture Substrates Using Robotic Microcontact Printing R- &#181;CP and Sequential Nucleophilic Substitution
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Dynamic self-correcting nucleophilic aromatic substitution.

Wen Jie Ong1, Timothy M Swager2

  • 1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, USA.

Nature Chemistry
|September 5, 2018
PubMed
Summary
This summary is machine-generated.

Dynamic covalent chemistry enables complex material synthesis. Nucleophilic aromatic substitution reactions were used to create novel redox-active thianthrene units, forming intricate molecular architectures.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Dynamic covalent chemistry (DCC) offers self-correction in synthesis.
  • Limited DCC reactions restrict material scope and functionality.
  • Nucleophilic aromatic substitution (SNAr) is explored as a new DCC reaction.

Purpose of the Study:

  • To investigate SNAr for DCC applications.
  • To synthesize novel materials using SNAr chemistry.
  • To explore the formation of molecular junctions and porous polymers.

Main Methods:

  • Condensation reactions between ortho-aryldithiols and ortho-aryldifluorides.
  • Utilizing SNAr to form redox-active thianthrene units.
  • Employing thermodynamic and kinetic control for regioselectivity.

Main Results:

  • Facile synthesis of two-, three-, and four-point molecular junctions with thianthrene moieties in high yields.
  • Demonstrated thermodynamic control for regioselectivity and kinetic control for other connections.
  • Successful synthesis of ladder macrocycles and porous polymer networks with high surface area (up to 813 m2/g).

Conclusions:

  • SNAr is a versatile DCC reaction for constructing complex molecular architectures.
  • The developed method allows for precise control over molecular connectivity.
  • This approach enables the creation of advanced porous materials with potential applications.