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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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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Metal-Ligand Bonds02:51

Metal-Ligand Bonds

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The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
21.6K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.9K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.9K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
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...
2.0K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.6K
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...
12.6K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.8K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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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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Ligand-Centered Hydrogen Evolution with Ni(II) and Pd(II)DMTH.

Christine A Phipps1, Dillon T Hofsommer1, Megan J Toda1

  • 1Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, United States.

Inorganic Chemistry
|June 10, 2022
PubMed
Summary

New nickel and palladium complexes with a unique ligand show high efficiency in catalyzing the hydrogen evolution reaction (HER). These electrocatalysts utilize a proton-coupled electron transfer mechanism for enhanced performance in renewable energy applications.

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Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase
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Area of Science:

  • Inorganic Chemistry
  • Electrocatalysis
  • Renewable Energy

Background:

  • The hydrogen evolution reaction (HER) is crucial for producing clean hydrogen fuel.
  • Developing efficient and robust electrocatalysts is key to advancing HER technologies.
  • Noninnocent ligands offer unique electronic properties for catalytic applications.

Purpose of the Study:

  • To synthesize and characterize novel nickel (Ni) and palladium (Pd) complexes for HER.
  • To investigate the catalytic mechanism and efficiency of these complexes.
  • To explore the role of ligand protonation in the electrocatalytic process.

Main Methods:

  • Synthesis and characterization of NiL1 and PdL1 complexes using spectroscopic and electrochemical techniques.
  • Spectrophotometric titration to determine the pKa of the hydrazino nitrogen.
  • Cyclic voltammetry to study redox properties and HER activity in acetonitrile.
  • Kinetic isotope effect (KIE) studies and Density Functional Theory (DFT) computations to elucidate the reaction mechanism.

Main Results:

  • NiL1 and PdL1 complexes were successfully synthesized and characterized.
  • The basic hydrazino nitrogen exhibited pKa values of 12.71 (NiL1) and 13.03 (PdL1).
  • High turnover frequencies were achieved: 6150 s-1 for NiL1 at 0.74 V and 8280 s-1 for PdL1 at 0.44 V.
  • KIE studies and DFT calculations indicated a ligand-centered HER mechanism involving proton-coupled electron transfer.

Conclusions:

  • The synthesized NiL1 and PdL1 complexes are highly effective electrocatalysts for the hydrogen evolution reaction.
  • The HER mechanism involves proton-coupled electron transfer, with the metal centers remaining in the +2 oxidation state.
  • These findings highlight the potential of noninnocent ligand-based complexes for efficient hydrogen production.