Video Experimental Relacionado

Updated: Apr 21, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Metátesis de enlace σ libre de metales en la activación del amoníaco por un diazadifosfataleno

Jingjing Cui¹, Yongxin Li, Rakesh Ganguly

¹Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, and ‡NTU-CBC Crystallography Facility, Nanyang Technological University , Singapore 637371, Singapore.

Journal of the American Chemical Society

|November 13, 2014

Resumen

Los investigadores sintetizaron un nuevo derivado del diazadifosfataleno que activa el amoníaco. Esta reacción, una metátesis formal de enlace sigma, produce un producto único de difosfoleno con un grupo de enamina.

Área de la Ciencia:

Química del organofosforo y su composición química.
Química inorgánica sintética química inorgánica sintética

Sus antecedentes:

Los derivados del diazadifosfapentaleno son nuevos compuestos heterocíclicos.
La activación de pequeñas moléculas como el amoníaco es crucial en la catálisis y la síntesis.

Objetivo del estudio:

Para sintetizar un derivado de diazadifosfataleno con una geometría doblada.
Para investigar la activación del amoníaco por este nuevo compuesto.
Para dilucidar el mecanismo de reacción utilizando métodos computacionales.

Principales métodos:

Síntesis de un derivado del diazadifosfataleno (compuesto 5).
Reacción del compuesto 5 con el amoníaco en condiciones suaves.
Cálculos de la teoría funcional de la densidad (DFT) para estudiar los mecanismos de reacción.

Principales resultados:

Síntesis exitosa del derivado de diazadifosfataleno doblado 5.
El compuesto 5 activó el amoníaco para formar un derivado 1-aza-2,3-difosfoleno (compuesto 6) con un grupo de enamina.
La reacción fue identificada como una metátesis formal de enlace sigma entre el enlace N-H del amoníaco y el enlace P-N en el compuesto 5.

Conclusiones:

Un nuevo derivado de diazadifosfataleno doblado activa efectivamente el amoníaco.
La reacción se produce a través de un mecanismo de metástasis de enlaces sigma.
Los cálculos de DFT proporcionan información sobre los procesos de activación e isomerización del amoníaco.

Más Videos Relacionados

Author Spotlight: Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers

Author Spotlight: Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers

Published on: May 12, 2023

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Videos de Conceptos Relacionados

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

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

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.

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

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.

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

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

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...

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

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,...