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Preparation of Nitriles01:12

Preparation of Nitriles

2.7K
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...
2.7K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

4.0K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
4.0K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

8.9K
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.
8.9K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.1K
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,...
3.1K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

5.5K
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.
5.5K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

5.0K
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.
5.0K

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Nitrilium ions - synthesis and applications.

Tom van Dijk1, J Chris Slootweg, Koop Lammertsma

  • 1Department of Chemistry and Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands. K.Lammertsma@vu.nl.

Organic & Biomolecular Chemistry
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Nitrilium ions, versatile organic chemistry reagents, are reviewed for their synthesis, stability, and reactivity. This work highlights their utility in creating imines, heterocycles, and in reactions with metal complexes.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Nitrilium ions are established organic chemistry reagents.
  • Recent research reveals greater versatility than previously recognized.
  • They exist as stable salts, in situ generated, or transient intermediates.

Purpose of the Study:

  • To provide a comprehensive review of nitrilium ion synthesis, stability, and reactivity.
  • To highlight nitrilium ions as synthons for imines and heterocycles.
  • To showcase their reactions with transition metal complexes.

Main Methods:

  • Literature review of nitrilium ion chemistry.
  • Analysis of synthetic routes and reaction mechanisms.
  • Compilation of applications in organic synthesis.

Main Results:

  • Nitrilium ions serve as valuable synthons for imine and diverse heterocycle synthesis.
  • Their reactivity extends to transition metal complex interactions.
  • Established methods allow for their generation and utilization.

Conclusions:

  • Nitrilium ions are accessible and simple reagents for organic synthesis.
  • A renewed focus on their utility is warranted.
  • They offer broad applications in creating complex organic molecules.