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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Nitrosation of Enols01:19

Nitrosation of Enols

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The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
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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.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Aromatic C-nitrosation by a copper(II)-nitrosyl complex.

Kanhu Charan Rout1, Biplab Mondal

  • 1Department of Chemistry, Indian Institute of Technology, Guwahati, Assam 781039, India. biplab@iitg.ernet.in.

Dalton Transactions (Cambridge, England : 2003)
|December 6, 2014
PubMed
Summary
This summary is machine-generated.

This study details the synthesis of a copper(II) complex and its reaction with nitric oxide. The reaction forms an unstable copper(II)-nitrosyl intermediate, leading to copper reduction and ligand C-nitrosation.

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Area of Science:

  • Inorganic Chemistry
  • Coordination Chemistry
  • Spectroscopy

Background:

  • Copper complexes are vital in catalysis and biological systems.
  • Nitric oxide (NO) plays diverse roles in biological and chemical processes.
  • Understanding metal-ligand interactions with NO is crucial for mechanistic studies.

Purpose of the Study:

  • To synthesize and characterize a novel copper(II) complex with 4-amino-3-hydroxy-1-sulphonic acid.
  • To investigate the reaction mechanism of this copper(II) complex with nitric oxide (NO).
  • To elucidate the formation of intermediates and subsequent reaction products.

Main Methods:

  • Synthesis and characterization of the copper(II) complex.
  • Reaction of the complex with nitric oxide in methanol.
  • Spectroscopic analysis including UV-visible and FT-IR spectroscopy.
  • Isolation and characterization of the C-nitrosation product.

Main Results:

  • Successful synthesis and characterization of the copper(II) complex.
  • Observation of an unstable copper(II)-nitrosyl intermediate upon NO addition.
  • Confirmation of intermediate formation via UV-visible and FT-IR spectroscopy.
  • Simultaneous C-nitrosation of the ligand's aromatic ring and reduction of the copper(II) center.
  • Isolation and full characterization of the final C-nitrosation product.

Conclusions:

  • The copper(II) complex reacts with nitric oxide via a copper(II)-nitrosyl intermediate.
  • This reaction pathway involves both copper center reduction and ligand modification (C-nitrosation).
  • The findings provide insights into the reactivity of copper complexes with nitric oxide.