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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.3K
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.
3.3K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

14.9K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
14.9K
Nucleophilic Substitution Reactions02:34

Nucleophilic Substitution Reactions

19.2K
Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
19.2K
¹H NMR of Labile Protons: Deuterium (²H) Substitution00:48

¹H NMR of Labile Protons: Deuterium (²H) Substitution

1.3K
This lesson illustrates the role of deuterium substitution in simplifying the NMR spectrum of compounds comprising labile protons. One method employed is the use of deuterium. Amongst the three isotopes of hydrogen, deuterium (2H) has a nucleus composed of one proton and one neutron. When the D2O solvent is added to a pure dry ethanol solution, its labile proton is substituted with deuterium.
1.3K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.7K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.7K
Predicting Products: Substitution vs. Elimination02:52

Predicting Products: Substitution vs. Elimination

13.9K
When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products.
The following factors can influence the mechanisms competing against each other:
13.9K

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Related Experiment Video

Updated: Jan 27, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.6K

Gold(III)-Substituted Carbenes.

Rui Wei1, Shuo Li1, Nina Albouy2

  • 1Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR 5069), CNRS/Université de Toulouse, 31062 Toulouse, France.

Journal of the American Chemical Society
|January 26, 2026
PubMed
Summary
This summary is machine-generated.

New gold(III)-substituted diazo compounds were synthesized and photolyzed to extrude dinitrogen. The resulting gold carbenes exhibit unique intramolecular and intermolecular reactivity, offering insights into gold carbene chemistry.

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Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII
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Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII

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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

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Last Updated: Jan 27, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Luminophore Formation in Various Conformations of Bovine Serum Albumin by Binding of GoldIII
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

9.0K

Area of Science:

  • Organometallic Chemistry
  • Photochemistry
  • Carbene Chemistry

Background:

  • Gold complexes are valuable in catalysis and synthesis.
  • Diazo compounds are versatile precursors for carbene generation.
  • Understanding gold carbene reactivity is crucial for developing new synthetic methodologies.

Purpose of the Study:

  • To synthesize and characterize novel Au(III)-substituted diazo compounds.
  • To investigate the photochemical extrusion of dinitrogen from these compounds.
  • To explore the reactivity of the generated Au(III) carbenes.

Main Methods:

  • Synthesis of (N^C^C)Au-diazo precursors.
  • UV-vis irradiation for dinitrogen extrusion.
  • Characterization of intermediates and products using spectroscopic methods.
  • Density Functional Theory (DFT) calculations.

Main Results:

  • Successful synthesis of Au(III)-substituted diazo compounds.
  • Photolytic dinitrogen extrusion yielding Au(III) carbenes.
  • Observation of intramolecular C-H insertion and β-H elimination for an Au-Dmp carbene.
  • Characterization of an Au-SiMe3 carbene via in crystallo photolysis.
  • Demonstration of intermolecular reactivity (H-abstraction, coupling) for the Au-SiMe3 carbene in solution.

Conclusions:

  • Au(III)-substituted diazo compounds are viable precursors for Au(III) carbenes.
  • The reactivity of Au(III) carbenes is influenced by the substituents.
  • Steric hindrance plays a role in directing carbene reaction pathways.
  • DFT calculations provide valuable insights into the electronic structure and reactivity of these species.