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Ajuste de la selectividad supramolecular para el hidrosulfuro: las relaciones de energía libre lineal revelan

Hazel A Fargher¹, Nathanael Lau¹, H Camille Richardson²

¹Department of Chemistry & Biochemistry, Materials Science Institute, and Knight Campus for Accelerating Scientific Impact, University of Oregon, Eugene, Oregon 97403-1253, United States.

Journal of the American Chemical Society

|April 14, 2020

Resumen

Los receptores supramoleculares muestran una mayor selectividad para los aniones de hidrosulfuro (HS-) sobre otros hidrocalogenuros y halogenuros. Esta selectividad es impulsada por los donantes de enlaces de hidrógeno arilo C-H, que guían el diseño futuro del receptor.

Área de la Ciencia:

Química supramolecular
Reconocimiento de aniones
Detección de sustancias químicas

Sus antecedentes:

Los aniones hidrocalcogénidos (HCh-) son biológicamente críticos pero son difíciles de unirse selectivamente.
El desarrollo de sondas supramoleculares selectivas para HCh- es esencial para los estudios biológicos y químicos.
Distinguir HCh- de haluros es un desafío clave en el diseño de receptores aniónicos.

Objetivo del estudio:

Investigar la selectividad de los receptores aniónicos supramoleculares para los aniones hidrocalcógenos (HCh-).
Comprender las propiedades fundamentales que rigen la unión y el reconocimiento de HCh.
Explorar la utilidad de las relaciones de energía libre lineal (LFER) en el diseño de receptores de aniones selectivos.

Principales métodos:

Relaciones de energía libre lineal utilizadas (LFER), incluidas las gráficas de Hammett y Swain-Lupton.
Empleó mapas de potencial electrostático para analizar las interacciones huésped-invitado.
Investigó la sensibilidad de los donantes de enlaces de hidrógeno arilo C-H a diferentes aniones.

Principales resultados:

Los LFER revelaron diferencias de sensibilidad distintas para los donantes de enlaces de hidrógeno arilo C-H hacia el hidrosulfuro (HS-) en comparación con otros haluros y HCh-.
Los mapas de potencial electrostático indicaron una preferencia específica del donante de arilo C-H para HS- dentro del andamio del huésped estudiado.
Se ha demostrado una mayor selectividad de HS con respecto a los aniones competidores.

Conclusiones:

Los LFER son herramientas poderosas para obtener información sobre el diseño del motivo para los receptores supramoleculares selectivos por aniones.
Los donantes de enlaces de hidrógeno Aryl C-H son cruciales para lograr el reconocimiento de HS-.
Los futuros receptores selectivos de HS deben investigar los donantes de enlaces de hidrógeno arilo C-H para una mayor selectividad.

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