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Related Concept Videos

Formation of Complex Ions03:45

Formation of Complex Ions

A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.

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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Dipyrrin based silver [2 + 2] metallamacrocycles.

Dmitry Pogozhev1, Stéphane A Baudron, Mir Wais Hosseini

  • 1Laboratoire de Chimie de Coordination Organique, UMR CNRS 7140, Université de Strasbourg, F-67000, Strasbourg, France.

Dalton Transactions (Cambridge, England : 2003)
|November 17, 2010
PubMed
Summary

This study reports the synthesis of novel silver metallamacrocycles using dipyrrin ligands and various silver salts. These robust cyclic complexes exhibit interesting solid-state structures and maintain integrity in solution.

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Published on: August 22, 2018

Area of Science:

  • Coordination Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Dipyrrin ligands are versatile building blocks for coordination complexes.
  • Silver(I) ions are known to form diverse supramolecular architectures.
  • Metallamacrocycles offer unique structural and functional properties.

Purpose of the Study:

  • To synthesize and characterize novel [2 + 2] silver metallamacrocycles.
  • To investigate the influence of anions and ligand structure on macrocycle formation and solid-state organization.
  • To assess the structural stability of these complexes in solution.

Main Methods:

  • Synthesis of silver metallamacrocycles using silver salts (AgX) and dipyrrin derivatives.
  • Characterization using X-ray crystallography, NMR spectroscopy (1H, 13C, DOSY).
  • Analysis of anion effects and hydrogen bonding on solid-state structure.

Main Results:

  • Successful synthesis of [2 + 2] silver metallamacrocycles with pyridyl and imidazolyl appended dipyrrins.
  • Solid-state structures are influenced by counter-anions (BF4-, PF6-, SbF6-, TfO-) and hydrogen bonding.
  • Argentophilic interactions (Ag(I)-Ag(I)) observed in some crystalline phases.
  • NMR studies confirmed the structural integrity and cyclic nature of the complexes in solution.

Conclusions:

  • The reported silver metallamacrocycles represent a new class of coordination compounds.
  • Anion and ligand design are crucial for controlling supramolecular assembly.
  • These complexes demonstrate robust structural characteristics in both solid and solution states.