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Reduction of Alkenes: Catalytic Hydrogenation

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...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Hybridization of Atomic Orbitals II

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization

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Selective Hydrogen Adsorption in Graphene Rotated Bilayers.

Ivan Brihuega¹, Felix Yndurain¹

¹Departamento de Física de la Materia Condensada and Condensed Matter Physics Center (IFIMAC), Universidad Autónoma de Madrid , Cantoblanco, 28049 Madrid, Spain.

The Journal of Physical Chemistry. B

|July 29, 2017

Summary

Atomic hydrogen preferentially chemisorbs on AA-stacked regions of rotated graphene bilayers. Doping and reduced rotation angles significantly enhance adsorption energy, with C-H bond energy impacting hydrogen and deuterium behavior.

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Area of Science:

Materials Science
Surface Science
Computational Chemistry

Background:

Graphene bilayers exhibit unique electronic properties influenced by interlayer rotation.
Understanding atomic hydrogen adsorption is crucial for graphene-based applications.

Purpose of the Study:

Investigate atomic hydrogen adsorption energies on rotated graphene bilayers.
Determine factors influencing hydrogen chemisorption strength and behavior.

Main Methods:

Ab initio calculations using density functional theory (DFT).
Inclusion of van der Waals interactions.
Analysis of electronic density of states and surface corrugation.

Main Results:

AA-stacked regions show preferential hydrogen chemisorption due to surface corrugation and electronic perturbations.
Adsorption energy differences can reach 80 meV.
Logarithmic van Hove singularities near the Dirac point enhance adsorption in doped graphene.
Adsorption energy increases as the rotation angle between layers decreases.
Significant C-H bond zero-point energy suggests differential adsorption/desorption for hydrogen and deuterium.

Conclusions:

Rotated graphene bilayers offer tunable hydrogen adsorption sites.
Electronic structure modifications significantly impact hydrogen binding.
Potential for selective hydrogen isotope interactions based on vibrational energies.