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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...

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...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

Redox Reactions

Redox Reactions

Redox reactions are vital biochemical processes that underpin energy metabolism in cells. These reactions involve the transfer of electrons between molecules, occurring in tandem as oxidation and reduction. Oxidation refers to the loss of electrons, while reduction denotes their gain. This coupling ensures the seamless flow of electrons through metabolic pathways. For example, in bacterial metabolism, glucose undergoes oxidation to carbon dioxide, while oxygen is simultaneously reduced to...

Redox Reactions

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Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...

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The removal of an electron from a molecule, results in a...

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Hydrogen Production and Utilization in a Membrane Reactor

Hydrogen Production and Utilization in a Membrane Reactor

Published on: March 10, 2023

Transfer hydrogenation as a redox process in nucleotides.

Florian Achrainer¹, Vladimir N Emel'yanenko, Waled Tantawy

¹Department of Chemistry, LMU München , Butenandtstrasse 5-13, D-81377 München, Germany.

The Journal of Physical Chemistry. B

|August 12, 2014

Summary

We determined the heats of hydrogenation for nucleotide bases. Uracil is the most easily hydrogenated, suggesting potential hydrogen transfer within oligonucleotides.

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Area of Science:

Biochemistry
Physical Chemistry
Computational Chemistry

Background:

Nucleotide bases are fundamental components of nucleic acids.
Understanding their chemical reactivity is crucial for molecular biology and drug design.
Hydrogenation enthalpies provide insights into the energetic stability and reactivity of these molecules.

Purpose of the Study:

To determine the heats of hydrogenation for key nucleotide bases: uracil, thymine, cytosine, adenine, and guanine.
To compare the hydrogenation enthalpies of these bases with model compounds.
To investigate the energetic feasibility of hydrogen transfer in oligonucleotide systems.

Main Methods:

Employed a combined theoretical and experimental approach.
Calculated and measured heats of hydrogenation for the specified nucleotide bases.
Utilized computational chemistry methods for theoretical predictions.
Performed experimental hydrogenation reactions for validation.

Main Results:

Determined the heats of hydrogenation for uracil, thymine, cytosine, adenine, and guanine.
Identified uracil as the most easily hydrogenated base, followed by thymine and cytosine.
Observed that uracil's hydrogenation enthalpy is comparable to that of sugar model ketones and aldehydes.

Conclusions:

The determined heats of hydrogenation offer quantitative measures of nucleotide base reactivity.
Uracil's high susceptibility to hydrogenation suggests a potential role in biological hydrogen transfer mechanisms.
Findings indicate the possibility of near-thermoneutral hydrogen transfer between uracil and the oligonucleotide sugar-phosphate backbone.