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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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π Molecular Orbitals of the Allyl Cation and Anion01:18

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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Anion-π Catalysis on Fullerenes.

Javier López-Andarias1, Antonio Frontera2, Stefan Matile1

  • 1School of Chemistry and Biochemistry, University of Geneva , Quai Ernest Ansermet 30, CH-1211 Geneva, Switzerland.

Journal of the American Chemical Society
|September 14, 2017
PubMed
Summary

This study explores anion-π interactions on fullerenes for catalysis. Tertiary amines enable selective acceleration of reactions like enolate addition and Diels-Alder, opening new avenues for carbon allotrope applications.

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Area of Science:

  • Supramolecular Chemistry
  • Catalysis
  • Materials Science

Background:

  • Anion-π interactions are underexplored in fullerene chemistry.
  • Fullerenes possess unique electronic properties (exchange-correlation, localized π holes) for catalysis.
  • Tertiary amines can be functionalized onto fullerene surfaces.

Purpose of the Study:

  • Investigate the potential of anion-π interactions on fullerenes for catalytic applications.
  • Explore the influence of tertiary amine positioning on fullerene catalytic activity.
  • Determine the selectivity and efficiency of fullerene-based catalysts in organic reactions.

Main Methods:

  • Computational simulations to model interactions and predict selectivity.
  • Synthesis of tertiary amine-functionalized fullerenes.
  • Experimental evaluation of catalytic performance in enolate addition and Diels-Alder reactions.

Main Results:

  • Stabilization of anionic transition states on fullerenes by anion-π interactions.
  • Enantioselective acceleration of disfavored enolate addition and exo Diels-Alder reactions.
  • Demonstrated discrimination between enolate tautomers based on planarization and charge delocalization.
  • Observed shorter enolate-π interactions on fullerenes compared to planar systems.

Conclusions:

  • Anion-π interactions on fullerenes offer unique catalytic selectivities.
  • Functionalized fullerenes can act as effective enantioselective catalysts.
  • These findings expand the scope of anion-π interactions and fullerene applications in catalysis.