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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...
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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.
Phase II Reactions: Miscellaneous Conjugation Reactions01:19

Phase II Reactions: Miscellaneous Conjugation Reactions

Phase II biotransformations are detoxification mechanisms that conjugate xenobiotics with endogenous substances, neutralizing their toxicity.
A key example involves the conjugation of cyanide ions, which impair cellular respiration and alter hemoglobin into non-oxygen-carrying cyanmethemoglobin. To neutralize this threat, a sulfur atom from thiosulphate is transferred to the cyanide ion, catalyzed by the enzyme rhodanese, resulting in an inactive compound called thiocyanate. The production of...

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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A highly reduced cyanogen ligand derived from cyanide reductive coupling.

Alexander R Fox1, Christopher C Cummins

  • 1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Room 6-435, Cambridge, MA 02139-4307, USA.

Chemical Communications (Cambridge, England)
|February 21, 2012
PubMed
Summary

Researchers synthesized a novel bimetallic cyanogen complex via reductive coupling of cyanide using a niobium(IV) precursor. DFT calculations elucidated the reaction mechanism, offering insights into inorganic synthesis and bonding.

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Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Computational Chemistry

Background:

  • Cyanide chemistry is crucial in various industrial and biological processes.
  • Niobium complexes are versatile in catalysis and materials science.
  • Understanding reductive coupling mechanisms is key to novel compound synthesis.

Purpose of the Study:

  • To synthesize and characterize a novel bimetallic cyanogen complex.
  • To investigate the reductive coupling of cyanide mediated by niobium.
  • To propose a mechanism for the observed coupling reaction using computational methods.

Main Methods:

  • Synthesis of a bimetallic cyanogen complex.
  • Structural characterization using spectroscopic techniques.
  • Density Functional Theory (DFT) calculations for mechanistic studies.

Main Results:

  • Successful synthesis of a unique bimetallic cyanogen complex.
  • Detailed structural and spectroscopic data were obtained.
  • A plausible mechanism for cyanide reductive coupling was proposed and supported by DFT.

Conclusions:

  • The study presents a new class of bimetallic cyanogen compounds.
  • The findings provide valuable insights into niobium-mediated cyanide transformations.
  • Computational modeling effectively elucidates reaction pathways in inorganic synthesis.