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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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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.
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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...
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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
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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).
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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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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.
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Aromaticity: what does it mean?

T M Krygowski1, H Szatylowicz2

  • 11Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland.

Chemtexts
|January 15, 2019
PubMed
Summary

Aromaticity in organic chemistry is complex, with multiple criteria like energy, geometry, and magnetism. This study compares these diverse aromaticity indices for various compounds, highlighting agreements and disagreements.

Keywords:
AromaticityHOMANICSPi-electron delocalizationResonance energyRing current

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry

Background:

  • Aromaticity is a fundamental concept in organic chemistry, but lacks a single, unambiguous definition.
  • Existing definitions rely on multiple criteria including energy, molecular geometry, magnetism, and reactivity.

Purpose of the Study:

  • To enumerate and compare various criteria used to define and assess aromaticity.
  • To analyze the agreement and disagreement between different aromaticity indices for selected compounds.

Main Methods:

  • Evaluation of energetic criteria (resonance energy, aromatic stabilization energy).
  • Assessment of molecular geometry using the harmonic oscillator model of aromaticity.
  • Application of magnetic criteria, including nucleus-independent chemical shifts (NICS), proton NMR chemical shifts, and magnetic susceptibility exaltation.
  • Comparison of indices across selected homo- and hetero-cyclic compounds.

Main Results:

  • Data for various aromaticity indices are presented in tables for selected compounds.
  • Illustrative examples demonstrate instances where different aromaticity criteria yield consistent or conflicting results.
  • The study highlights the multifaceted nature of aromaticity and the challenges in its unified definition.

Conclusions:

  • Aromaticity is a multifaceted property best understood through a combination of diverse criteria.
  • Comparing various indices provides deeper insights into the electronic and structural characteristics of aromatic systems.
  • Further research is needed to reconcile discrepancies between different aromaticity measures.