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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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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...
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Hydrogen Bonds01:04

Hydrogen Bonds

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A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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¹H NMR of Labile Protons: Deuterium (²H) Substitution00:48

¹H NMR of Labile Protons: Deuterium (²H) Substitution

1.0K
This lesson illustrates the role of deuterium substitution in simplifying the NMR spectrum of compounds comprising labile protons. One method employed is the use of deuterium. Amongst the three isotopes of hydrogen, deuterium (2H) has a nucleus composed of one proton and one neutron. When the D2O solvent is added to a pure dry ethanol solution, its labile proton is substituted with deuterium.
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.4K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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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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Aldehydes and Ketones with Water: Hydrate Formation01:20

Aldehydes and Ketones with Water: Hydrate Formation

3.9K
An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
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Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
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Reversible hydrogen adsorption at room temperature using a molybdenum-dihydrogen complex in the solid state.

Kaiji Uchida1, Naoki Kishimoto1, Shin-Ichiro Noro2

  • 1Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. shinya.takaishi.d8@tohoku.ac.jp.

Dalton Transactions (Cambridge, England : 2003)
|September 21, 2021
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Summary

Solid-state dihydrogen complexes offer reversible hydrogen storage. A specific molybdenum complex synthesized via N2-adduct removal shows ideal H2 adsorption above room temperature.

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Area of Science:

  • Materials Chemistry
  • Inorganic Chemistry
  • Hydrogen Storage

Background:

  • Reversible hydrogen storage under mild conditions is a key goal in materials chemistry.
  • Dihydrogen complexes are promising due to moderate H2 adsorption enthalpy without H-H bond cleavage.
  • Solid-state studies on dihydrogen complex H2 adsorption are limited.

Purpose of the Study:

  • To investigate the solid-state hydrogen adsorption properties of a 16-electron molybdenum precursor complex ([Mo(PCy3)2(CO)3]).
  • To compare H2 adsorption behavior of complexes synthesized via different routes.
  • To elucidate the factors influencing H2 adsorption enthalpy in the solid state.

Main Methods:

  • Synthesis of the 16-electron precursor complex ([Mo(PCy3)2(CO)3]) through direct synthesis under Ar (1) and N2-adduct removal under vacuum (2).
  • Evaluation of H2 adsorption/desorption properties in the solid state.
  • Density Functional Theory (DFT) calculations to analyze adsorption mechanisms and energetics.

Main Results:

  • Complex 2 exhibited ideal Langmuir-type reversible H2 ad/desorption above room temperature.
  • Complex 1 displayed irreversible H2 adsorption.
  • The H2 adsorption enthalpy for complex 2 in the solid state was greater than in THF solution, attributed to the absence of agostic interactions.

Conclusions:

  • Solid-state synthesis route significantly impacts H2 storage properties of dihydrogen complexes.
  • The N2-adduct removal method yields a material suitable for reversible hydrogen storage under mild conditions.
  • DFT calculations confirm the role of agostic interactions in modulating solid-state H2 adsorption enthalpy.