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Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair of nonbonding electrons, aliphatic amines can also act as Lewis bases by forming a covalent bond with an electrophile.
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Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:
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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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Brønsted-Lowry acid-base chemistry is the transfer of protons; thus, logic suggests a relation between the relative strengths of conjugate acid-base pairs. The strength of an acid or base is quantified in its ionization constant, Ka or Kb, which represents the extent of the acid or base ionization reaction. For the conjugate acid-base pair HA / A−, the ionization equilibrium equations and ionization constant expressions are
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Parámetros del receptor de enlaces H para los aniones

Sarah J Pike1, Jordan J Hutchinson2, Christopher A Hunter1

  • 1Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.

Journal of the American Chemical Society
|May 5, 2017
PubMed
Resumen

Este estudio cuantifica las fuerzas de enlace de hidrógeno para varios aniones utilizando titulaciones UV/vis. Los parámetros de enlace H de aniones (β) son transferibles entre disolventes y donantes, lo que permite una predicción precisa del reconocimiento de aniones.

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Área de la Ciencia:

  • Química supramolecular
  • Química analítica
  • Química Física y Orgánica

Sus antecedentes:

  • El enlace de hidrógeno juega un papel crucial en el reconocimiento molecular y el autoensamblaje.
  • La cuantificación de la fuerza del aceptor de enlaces de hidrógeno (HBA) de los aniones es esencial para comprender sus interacciones en solución.
  • Los estudios anteriores a menudo se han centrado en pares de donantes de aniones específicos o sistemas de disolventes limitados.

Objetivo del estudio:

  • Investigar y cuantificar sistemáticamente los parámetros del aceptor de enlaces de hidrógeno (HBA) (β) para un conjunto diverso de 15 aniones.
  • Evaluar la transferibilidad de estos parámetros de HBA a través de diferentes donantes de enlaces de hidrógeno neutrales (HBD) y disolventes orgánicos (cloroformo y acetonitrilo).
  • Establecer un método fiable para predecir las propiedades de reconocimiento de aniones en diversos entornos químicos.

Principales métodos:

  • Utilizando las titulaciones de absorción UV/vis para controlar la formación de complejos enlazados por hidrógeno entre los aniones y los HBD neutros.
  • Utilizando una serie de 15 aniones diferentes y 3 HBDs distintos tanto en cloroformo como en acetonitrilo.
  • Análisis de los datos de titulación para obtener parámetros HBA autoconsistentes (β) para cada anión.

Principales resultados:

  • Determinados parámetros autoconsistentes de HBA (β) para 15 aniones, incluidos haluros, carboxilatos y sulfonatos.
  • Demostró la transferibilidad de los parámetros aniónicos de HBA a través de diferentes disolventes y socios de HBD.
  • Carboxilatos identificados como HBAs excepcionalmente fuertes (β ≈ 15), que exceden significativamente los HBAs orgánicos neutros.
  • Se encontró que el hexafluorofosfato era el HBA más débil entre los estudiados, comparable a la piridina.
  • Efectos negligibles confirmados del emparejamiento de iones con contra-cationes bajo condiciones específicas.

Conclusiones:

  • Los parámetros de HBA de aniones (β) son robustos y transferibles, lo que permite el reconocimiento predecible de aniones.
  • La fuerza HBA de los aniones no está correlacionada con el pKa de sus ácidos conjugados.
  • Este trabajo proporciona un marco cuantitativo valioso para el diseño de sistemas con capacidades específicas de unión de aniones.