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

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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...
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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Diazonium Group Substitution: –OH and –H01:19

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Nitriles to Amines: LiAlH4 Reduction00:55

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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...
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Preparation of Nitriles01:12

Preparation of Nitriles

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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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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Dinitrogen Activation by Dihydrogen and a PNP-Ligated Titanium Complex.

Baoli Wang1, Gen Luo1, Masayoshi Nishiura1

  • 1Organometallic Chemistry Laboratory and RIKEN Center for Sustainable Resource Science , RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.

Journal of the American Chemical Society
|January 31, 2017
PubMed
Summary

Researchers explored the hydrogenation of dinitrogen (N2) using titanium complexes. They discovered a pathway from a dinitrogen complex to an imido/nitrido complex, revealing insights into nitrogen fixation mechanisms.

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Catalysis

Background:

  • Titanium complexes with PNP ligands are known to activate small molecules.
  • Dinitrogen (N2) activation and functionalization remain a significant challenge in chemistry.

Purpose of the Study:

  • To investigate the hydrogenolysis of a titanium dialkyl complex with dinitrogen (N2) and hydrogen (H2).
  • To elucidate the mechanism of N2 hydrogenation and subsequent transformations.

Main Methods:

  • Synthesis and characterization of titanium complexes.
  • Reactions involving hydrogenolysis and hydrogenation under controlled conditions.
  • Density functional theory (DFT) calculations to study reaction mechanisms.

Main Results:

  • Formation of a binuclear titanium dinitrogen complex from the titanium dialkyl precursor.
  • Conversion of the dinitrogen complex to a μ2-imido/μ2-nitrido/hydrido complex upon heating with H2.
  • DFT calculations provided insights into the mechanistic pathway of N2 hydrogenation.

Conclusions:

  • The study demonstrates a novel transformation of a dinitrogen ligand to imido and nitrido species.
  • The findings contribute to understanding the fundamental steps in dinitrogen reduction and functionalization.
  • This work offers potential avenues for developing new catalytic systems for nitrogen conversion.