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Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
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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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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 Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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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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The vibrational frequency of a bond is directly proportional to its bond strength. As a result, stronger bonds vibrate at higher frequencies, while weaker bonds vibrate at lower frequencies. The stretching vibration of the strong O–H bond in alcohols and phenols (very dilute solution or gas phase) appears as a sharp peak at 3600–3650 cm−1.
However, the extent of hydrogen bonding influences the observed stretching frequency and band broadening. Intermolecular or intramolecular...
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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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Hidrogenación electrocatalítica eficiente con un reactor de membrana de paladio

Rebecca S Sherbo1, Aiko Kurimoto1, Christopher M Brown1

  • 1Department of Chemistry , The University of British Columbia , 2036 Main Mall , Vancouver , British Columbia V6T 1Z1 , Canada.

Journal of the American Chemical Society
|April 19, 2019
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Resumen

Este estudio introduce un reactor electroquímico de membrana de paladio para la hidrogenación, mejorando las velocidades de reacción y la eficiencia del voltaje. Este método permite la hidrogenación en disolventes orgánicos sin contaminación por hidrógeno gaseoso o electrolitos.

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Área de la Ciencia:

  • La electroquímica
  • Química orgánica
  • Ingeniería Química

Sus antecedentes:

  • La hidrogenación tradicional a menudo requiere hidrógeno gaseoso (H2), lo que plantea desafíos de seguridad y manejo.
  • Los métodos electroquímicos para la hidrogenación generalmente implican una reacción directa en un electrodo, lo que limita la compatibilidad y la eficiencia del disolvente.

Objetivo del estudio:

  • Para demostrar las ventajas de un reactor de membrana de paladio para la hidrogenación electroquímica.
  • Mostrar mejores velocidades de reacción y eficiencia de voltaje en comparación con los métodos tradicionales.
  • Para permitir la hidrogenación en diversos disolventes orgánicos sin contaminación por electrolitos.

Principales métodos:

  • Utilizando una membrana de paladio para separar físicamente los compartimentos electroquímicos y de hidrogenación.
  • Realización de la hidrogenación electrocatalítica mediante el uso de protones en varios disolventes orgánicos.
  • Comparación de las velocidades de reacción y la eficiencia del voltaje con la hidrogenación convencional basada en electrodos.

Principales resultados:

  • El reactor de membrana de paladio mejora significativamente las tasas de reacción de hidrogenación.
  • Se obtiene una mayor eficiencia de voltaje en comparación con la hidrogenación directamente en un electrodo.
  • La hidrogenación puede realizarse con éxito en disolventes orgánicos, sin interferencia de electrolitos.

Conclusiones:

  • El reactor de membrana de paladio ofrece una alternativa más segura y eficiente para la hidrogenación electroquímica.
  • Esta tecnología amplía el alcance de las reacciones orgánicas impulsadas electrolíticamente.
  • El manejo y la purificación simplificados de los reactivos son las ventajas clave de este enfoque.