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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

5.3K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

5.4K
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.
5.4K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.1K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
3.1K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

2.3K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
2.3K
Preparation of Nitriles01:12

Preparation of Nitriles

2.0K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.0K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.6K
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.
3.6K

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Nitration of Deactivated Aromatic Compounds Using Lithium Nitrate.

Weihao Ma1, J Tyler McBride1, Robert S Phillips1,2

  • 1Department of Chemistry, University of Georgia, Athens 30602, Georgia.

Tetrahedron Letters
|May 1, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a new, practical method for electrophilic nitration of deactivated aromatic compounds using lithium nitrate and acid catalysts. This approach offers moderate to excellent yields under mild conditions, making nitro compound synthesis feasible.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Material Science

Background:

  • Nitroarenes are vital building blocks in pharmaceuticals, materials, and industrial chemistry.
  • Electrophilic nitration of deactivated aromatic compounds remains a synthetic challenge.

Purpose of the Study:

  • To develop a novel and efficient strategy for the electrophilic nitration of deactivated aromatic compounds.
  • To provide a practical and commercially viable method for synthesizing nitro compounds.

Main Methods:

  • Utilized lithium nitrate (LiNO3) as the nitrating agent.
  • Employed sulfuric acid in trifluoroacetic acid as the reaction medium and catalyst system.
  • Investigated the electrophilic nitration of various deactivated aromatic substrates.

Main Results:

  • Achieved moderate to excellent yields for the synthesized nitroarenes.
  • Demonstrated the effectiveness of the LiNO3/H2SO4/TFA system for nitration.
  • Confirmed the mild reaction conditions and straightforward workup procedures.

Conclusions:

  • The developed method offers a practical and efficient route for synthesizing nitro compounds.
  • This strategy is suitable for both laboratory-scale and potential industrial applications.
  • The use of readily available reagents and mild conditions enhances the feasibility of nitroarene production.