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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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.
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Electron Behavior

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Electrons are negatively charged subatomic particles that are attracted to an orbit around the positively-charged nucleus of an atom. They reside in locations that are associated with energy levels called shells and are further organized into sub-shells and orbitals within each shell.
Electrons Orbit the Nucleus
Electrons are found in specific locations outside of the nucleus. The shell in which an electron resides indicates the general energy level of the electron: those closer to the...
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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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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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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Deshidrogenación catalizada por electrones en una unión de una sola molécula

Hongliang Chen1,2,3, Feng Jiang4, Chen Hu5

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States.

Journal of the American Chemical Society
|May 27, 2021
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Resumen

Los electrones pueden desencadenar inesperadamente reacciones químicas en moléculas individuales, alterando sus propiedades eléctricas. Este estudio revela que la catálisis de electrones impulsa la transformación de etano a eteno en las uniones moleculares, lo que afecta las mediciones de conductividad.

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Área de la Ciencia:

  • La electrónica molecular
  • Ciencias de la superficie
  • Catálisis

Sus antecedentes:

  • El transporte de electrones a través de moléculas individuales es un área clave en la electrónica molecular.
  • Los electrones pueden actuar como catalizadores para las reacciones radicales, un factor a menudo pasado por alto en los estudios de conductividad.
  • Las reacciones inesperadas mediadas por electrones pueden influir en las mediciones en las uniones de una sola molécula.

Objetivo del estudio:

  • Investigar las relaciones estructura-propiedad contraintuitivas en la conductividad molecular.
  • Para demostrar y comprender la catálisis de electrones en uniones de una sola molécula.
  • Explorar el mecanismo de la transformación de etano a eteno catalizado por electrones.

Principales métodos:

  • Fabricación y caracterización de las uniones de una sola molécula.
  • Experimentos de conjunto electroquímico.
  • Cálculos teóricos (por ejemplo, teoría funcional de la densidad).

Principales resultados:

  • Las moléculas con espina dorsal de bipiridinio etano saturado mostraron una conductividad similar a las con espina dorsal de bipiridinio etano conjugado.
  • Se observó una transformación de etano a eteno en la unión de una sola molécula.
  • Se encontró que los electrones desencadenan el proceso redox, y el campo eléctrico promueve la deshidrogenación.

Conclusiones:

  • La catálisis de electrones juega un papel crítico en la interpretación de los datos de conductividad de una sola molécula.
  • Una transformación de etano a eteno ocurre a través de la deshidrogenación catalizada por electrones dentro de la unión.
  • Este trabajo proporciona información sobre los mecanismos de producción de hidrógeno electrocatalítico a nivel de una sola molécula.