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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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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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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...
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2° Amines to N-Nitrosamines: Reaction with NaNO2

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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

4.0K
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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Nitriles to Ketones: Grignard Reaction00:57

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4.8K
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...
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Tip-Induced Nitrene Generation.

Leonard-Alexander Lieske1, Aaron H Oechsle1, Igor Rončević2

  • 1IBM Research Europe - Zurich, Rüschlikon 8803, Switzerland.

ACS Nano
|August 28, 2025
PubMed
Summary
This summary is machine-generated.

Researchers created a novel molecule, trinitreno-s-heptazine, with three reactive nitrene centers. This high-spin molecule exhibits unique magnetic properties, transitioning from a septet to a sextet ground state under specific conditions.

Keywords:
atomic force microscopycomputational chemistrynitrene chemistryon-surface synthesistip-induced chemistry

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Area of Science:

  • * Surface science
  • * Molecular chemistry
  • * Quantum magnetism

Background:

  • * Molecules with multiple nitrene centers are of interest for their unique electronic and magnetic properties.
  • * Tip-induced chemistry offers a pathway for on-surface synthesis of novel molecular structures.
  • * Understanding the spin states and magnetic coupling in such systems is crucial for potential applications.

Purpose of the Study:

  • * To synthesize and characterize trinitreno-s-heptazine, a molecule with three nitrene centers.
  • * To investigate the magnetic coupling and ground state spin of the molecule.
  • * To explore the influence of the surface environment on the molecule's properties.

Main Methods:

  • * On-surface synthesis using tip-induced chemistry on a NaCl/Au(111) surface.
  • * Characterization using atomic force microscopy (AFM) and scanning tunneling microscopy (STM).
  • * Theoretical calculations including broken-symmetry density functional theory (DFT) and configuration interaction (CI).

Main Results:

  • * Successful generation of mono-, di-, and trinitreno-s-heptazine from a triazido precursor.
  • * Experimental evidence for the formation of molecules with one to three nitrene centers.
  • * Theoretical prediction of ferromagnetic coupling between nitrene centers, leading to a high-spin septet ground state in the gas phase.
  • * Experimental and theoretical indication of an anionic sextet ground state for trinitreno-s-heptazine on the NaCl/Au(111) surface.

Conclusions:

  • * Trinitreno-s-heptazine can be synthesized on-surface via tip-induced chemistry.
  • * The molecule exhibits tunable magnetic properties dependent on its environment (gas phase vs. surface).
  • * This work provides insights into the synthesis and magnetic behavior of high-spin molecules on surfaces.