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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

3.9K
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.
3.9K
Metal-Ligand Bonds02:51

Metal-Ligand Bonds

21.1K
The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
21.1K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.2K
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.
6.2K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.3K
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...
3.3K
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

572
In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
572
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
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.
2.8K

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Updated: Jul 27, 2025

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
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Dinitrogen Binding and Functionalization from a Low-Coordinate Alkynyliron Complex.

Samuel M Bhutto1, Brandon Q Mercado1, Patrick L Holland1

  • 1Department of Chemistry, Yale University, New Haven, Connecticut 06511, United States.

Inorganic Chemistry
|June 9, 2023
PubMed
Summary

Iron(I) alkynyl complexes can bind nitrogen (N2), forming a stable complex. Silylation yields a disilylhydrazido complex, where the alkynyl group resists migration due to strong iron-carbon bonds.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry

Background:

  • Low-coordinate transition metal complexes offer unique steric and electronic properties.
  • Alkynyl ligands present interesting bonding and reactivity profiles.

Purpose of the Study:

  • To investigate the nitrogen (N2) binding capabilities of iron(I) alkynyl complexes.
  • To characterize the resulting N2 complex and its derivatives.

Main Methods:

  • Synthesis and isolation of iron(I) alkynyl complexes.
  • X-ray crystallography for structural determination.
  • Silylation reactions.
  • Natural Bond Orbital (NBO) analysis.
  • Density Functional Theory (DFT) calculations.

Main Results:

  • Isolation and structural characterization of an iron(I) N2 complex.
  • Formation of a stable, isolable iron complex with a disilylhydrazido(2-) ligand upon silylation.
  • NBO analysis suggests an iron(II) formulation is more accurate for the silylated complex.
  • The alkynyl ligand did not undergo migration, unlike a previously reported phenyl analogue.
  • DFT calculations identified a strong iron-carbon bond energy as a key factor for the alkynyl group's resistance to migration.

Conclusions:

  • Iron(I) alkynyl complexes are capable of binding molecular nitrogen.
  • Silylation provides a route to novel iron-silylhydrazido complexes.
  • The alkynyl ligand's resistance to migration is attributed to its strong bond with iron, contrasting with phenyl ligands.