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Carbocations02:10

Carbocations

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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Formation of Complex Ions03:45

Formation of Complex Ions

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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...
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Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

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The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π...
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Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives01:15

Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

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Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and their derivatives. In these reactions, the leaving group attached to the acyl group is substituted by a nucleophile. The general mechanism proceeds via two steps.
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Electrophiles02:28

Electrophiles

12.9K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

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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...
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Synthesis and Characterization of Amphiphilic Gold Nanoparticles
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A Nucleophilic Gold(III) Carbene Complex.

Anthony Pujol1, Mathieu Lafage1, Feriel Rekhroukh1

  • 1Laboratoire Hétérochimie Fondamentale et Appliquée, Université Paul Sabatier/CNRS UMR 5069, 118 Route de Narbonne, 31062, Toulouse Cedex, France.

Angewandte Chemie (International Ed. in English)
|August 8, 2017
PubMed
Summary

Researchers synthesized the first gold(III) carbene complex, revealing its nucleophilic character. This novel gold carbene complex undergoes C=C coupling reactions with electrophiles.

Keywords:
C=C couplingcarbene complexesgeminal dianionsgold(III)nucleophilic Schrock-type carbenes

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Area of Science:

  • Organometallic Chemistry
  • Gold Chemistry
  • Carbene Complexes

Background:

  • Gold complexes are versatile catalysts and reagents in organic synthesis.
  • Carbene ligands play a crucial role in stabilizing metal centers and influencing reactivity.
  • Cyclometalated gold complexes offer unique structural and electronic properties.

Purpose of the Study:

  • To synthesize and characterize the first gold(III) carbene complex.
  • To investigate the electronic structure and bonding of this novel complex.
  • To explore the reactivity of the gold(III) carbene complex with electrophiles.

Main Methods:

  • Synthesis of the gold(III) carbene complex via reaction of a geminal dianion with a (P,C) cyclometalated gold(III) precursor.
  • Structural and bonding analysis using experimental techniques (e.g., X-ray crystallography, NMR spectroscopy).
  • Computational investigations (e.g., DFT calculations) to understand electronic properties, including the highest occupied molecular orbital (HOMO).

Main Results:

  • Successful preparation and full characterization of the unprecedented gold(III) carbene complex.
  • Identification of a high-energy HOMO centered at the carbene carbon, indicating significant nucleophilic character.
  • Demonstration of C=C coupling reactions with electrophiles such as phenyl isothiocyanate (PhNCS) and carbon disulfide (CS2).

Conclusions:

  • The synthesized gold(III) carbene complex exhibits unique nucleophilic behavior due to its electronic structure.
  • This discovery opens new avenues for gold-mediated organic transformations and C-C bond formation.
  • The reactivity profile of this novel gold carbene complex expands the scope of organogold chemistry.