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Related Concept Videos

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
Preparation of Nitriles01:12

Preparation of Nitriles

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...
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...
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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The first actinyl cyanide.

Jean-Claude Berthet1, Pierre Thuéry, Michel Ephritikhine

  • 1Service de Chimie Moléculaire, DSM, DRECAM, CNRS URA 331, Laboratoire Claude Fréjacques, CEA Saclay, Gif-sur-Yvette, 91191, France. jean-claude.berthet@cea.fr

Chemical Communications (Cambridge, England)
|February 1, 2007
PubMed
Summary

Researchers synthesized a novel pentacyano uranyl complex, [NEt4]3[UO2(CN)5], by reacting uranyl triflate with tetraethylammonium cyanide. This monomeric complex features five C-coordinated cyanide ligands arranged equatorially around the uranyl core.

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Area of Science:

  • Inorganic Chemistry
  • Coordination Chemistry
  • Uranium Chemistry

Background:

  • Uranium oxides are crucial in nuclear energy and research.
  • Understanding the coordination chemistry of uranyl ions is key to developing new materials and applications.
  • Cyanide ligands offer versatile coordination modes for metal complexes.

Purpose of the Study:

  • To synthesize and characterize a novel pentacyano uranyl complex.
  • To investigate the coordination environment of the uranyl ion with cyanide ligands.
  • To determine the structural and bonding properties of the resulting complex.

Main Methods:

  • Reaction of uranyl triflate (UO2(OTf)2) with tetraethylammonium cyanide (NEt4CN) in acetonitrile.
  • Isolation and purification of the resulting pentacyano uranyl complex, [NEt4]3[UO2(CN)5].
  • Solid-state structural analysis using X-ray diffraction to determine the coordination geometry.

Main Results:

  • Successful synthesis of the pentacyano uranyl complex [NEt4]3[UO2(CN)5].
  • The complex is monomeric in the solid state.
  • Five cyanide ions coordinate to the uranyl core in the equatorial plane, forming a pentagonal bipyramidal geometry around the uranium atom.
  • The cyanide ligands are C-coordinated, indicating bonding through the carbon atom.

Conclusions:

  • The reaction provides a new route to pentacyano uranyl complexes.
  • The C-coordinated cyanide ligands adopt an equatorial arrangement, influencing the overall structure.
  • This study expands the understanding of uranyl coordination chemistry and the behavior of cyanide ligands in actinide complexes.