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Videos de Conceptos Relacionados

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

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sp3d and sp3d 2 Hybridization
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

3.4K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.4K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

4.0K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
4.0K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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Diazofosfano HPN2

Bo Lu1, Xin Shao1, Xin Jiang1

  • 1Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Fudan University, Shanghai 200433, China.

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|November 29, 2022
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Resumen

Los investigadores sintetizaron el diazofosfano (HPN2), un análogo pesado del ácido hidrazóico, utilizando reacciones fotolíticas. Este estudio caracteriza el HPN2 y sus productos de fotólisis, incluido el radical fosfinilo (•PN2).

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Área de la Ciencia:

  • Química inorgánica
  • La fotoquímica
  • Química computacional

Sus antecedentes:

  • El diazofosfano (HPN2) es un análogo pesado del ácido hidrazoico (HN3).
  • La síntesis y caracterización de nuevos compuestos de fósforo y nitrógeno son de gran interés.
  • Comprender el comportamiento fotolítico de tales compuestos puede revelar nuevas vías de reacción e intermedios reactivos.

Objetivo del estudio:

  • Sintetizar y caracterizar el diazofosfano (HPN2) y sus isotopólogos.
  • Para investigar las reacciones fotolíticas de HPN2 en diferentes longitudes de onda.
  • Explorar la generación potencial de nuevas especies reactivas como el radical fosfinilo (•PN2).

Principales métodos:

  • Técnicas de aislamiento de matriz a baja temperatura (10 K).
  • Las reacciones fotolíticas que utilizan la irradiación UV (193 nm, 365 nm, 266 nm).
  • Caracterización mediante espectroscopia de aislamiento de matriz en el infrarrojo (IR) y en el ultravioleta visible (UV-vis).
  • Los cálculos químicos cuánticos de apoyo (CCSD(T) -F12a/cc-pVTZ-F12).

Principales resultados:

  • Síntesis exitosa de diazofosfano (HPN2) a partir del nitrógeno molecular (N2) y la fosfina (PH3) o el fosfateno (HPCO).
  • Caracterización de HPN2, DPN2 y HP15N2 utilizando métodos espectroscópicos y soporte computacional.
  • La fotólisis a 266 nm conduce a la escisión del enlace P-N en el HPN2.
  • La fotólisis a 193 nm genera el radical fosfinilo (•PN2).

Conclusiones:

  • El diazofosfano (HPN2) puede sintetizarse en condiciones fotolíticas específicas a baja temperatura.
  • Los datos espectroscópicos y computacionales confirman la estructura de HPN2 y sus isotopólogos.
  • HPN2 exhibe fotólisis dependiente de la longitud de onda, produciendo diferentes productos, incluido el radical fosfinilo previamente esquivo (•PN2).