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Related Concept Videos

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the surface of...
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Heterogeneous Catalysis01:22

Heterogeneous Catalysis

Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic factors, steric factors also account...

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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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Stability-enhanced hydrogen-evolving dirhodium photocatalysts through ligand modification.

Noémie Elgrishi1, Thomas S Teets, Matthew B Chambers

  • 1Department of Chemistry, 6-355, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139-4307, USA.

Chemical Communications (Cambridge, England)
|August 18, 2012
PubMed
Summary

A novel rhodium complex (Rh(2)(0,II)(tfepma)(2)(CN(t)Bu)(2)Cl(2)) efficiently splits hydrogen chloride (HCl) to produce hydrogen (H(2)). A modified version with adamantyl isocyanide (CNAd) shows significantly improved stability and sustained H(2) generation.

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Area of Science:

  • Inorganic Chemistry
  • Photocatalysis
  • Sustainable Energy

Background:

  • Mixed-valent rhodium dimers are explored for catalytic applications.
  • Hydrogen production from HCl splitting is a key goal in sustainable chemistry.
  • Catalyst stability remains a challenge in photocatalytic hydrogen generation.

Purpose of the Study:

  • To investigate the photocatalytic activity of Rh(2)(0,II)(tfepma)(2)(CN(t)Bu)(2)Cl(2) for HCl splitting.
  • To enhance the stability and longevity of the rhodium catalyst for sustained hydrogen production.
  • To compare the performance of a tert-butyl isocyanide ligand versus an adamantyl isocyanide ligand.

Main Methods:

  • Synthesis and characterization of two-electron mixed-valent rhodium complexes.
  • Photocatalytic hydrogen production experiments using HCl as a source.
  • Long-term stability studies monitoring hydrogen evolution over time.
  • Analysis of catalyst degradation pathways.

Main Results:

  • The initial complex Rh(2)(0,II)(tfepma)(2)(CN(t)Bu)(2)Cl(2) demonstrated photocatalytic HCl splitting, producing H(2).
  • The catalyst exhibited rapid degradation, ceasing H(2) production after approximately 36 hours (3 turnovers).
  • A modified complex, Rh(2)(0,II)(tfepma)(2)(CNAd)(2)Cl(2), showed enhanced stability, with sustained H(2) production for over 144 hours (7 turnovers).

Conclusions:

  • The choice of isocyanide ligand significantly impacts the stability of rhodium-based photocatalysts for HCl splitting.
  • The adamantyl isocyanide ligand confers superior stability, enabling prolonged hydrogen production.
  • This research offers a pathway towards more robust and efficient catalysts for sustainable hydrogen generation.