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Reducción electroquímica del grupo funcional carbonilo: la importancia de la geometría de adsorción, la estructura
Christoph J Bondue1, Marc T M Koper1
1Leiden Institute of Chemistry , Leiden University , P.O. Box 9502, 2300 RA Leiden , The Netherlands.
Journal of the American Chemical Society
|July 6, 2019
Resumen
La hidrogenación electroquímica de las cetonas está influenciada por la estructura molecular. Los anillos de fenilo mejoran la actividad de la superficie del platino, mientras que los anillos de piridina la inhiben debido a la interacción del átomo de nitrógeno, controlando la electrorreducción selectiva.
Área de la Ciencia:
- La electroquímica
- Ciencias de la superficie
- Catálisis
Sus antecedentes:
- Investigación de la hidrogenación electroquímica de los grupos carbonilo en cetonas funcionalizadas.
- Comprender el papel de la estructura molecular y la superficie del catalizador en las vías de reacción.
Objetivo del estudio:
- Para aclarar la influencia de los anillos de fenilo y piridina en la hidrogenación de la acetofenona y la 4-acetilpiridina en los electrodos de platino.
- Para comparar estos efectos con la hidrogenación con acetona, con un grupo carbonilo aislado.
Principales métodos:
- Experimentos de hidrogenación electroquímica con electrodos de un solo cristal de platino.
- Análisis del comportamiento de adsorción y la selectividad de la reacción basada en la superficie y la estructura molecular.
Principales resultados:
- La hidrogenación con acetona está limitada en Pt{11} y Pt{100} debido a la débil adsorción de carbonilo.
- La hidrogenación de la acetofenona es facilitada por la adsorción del anillo fenílico, activando Pt111 y Pt100.
- La interacción de nitrógeno del anillo de piridina conduce a la adsorción vertical, inhibiendo la hidrogenación en todas las superficies de platino.
Conclusiones:
- La estructura de la superficie del catalizador y la estructura molecular del reactivo dictan la electroreducción selectiva de cetonas funcionalizadas.
- El anillo fenilo activa las superficies específicas de platino, mientras que el anillo de piridina las desactiva para la hidrogenación.
- La comprensión de estas interacciones es crucial para el diseño de procesos catalíticos selectivos.
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