Video Experimental Relacionado

Updated: May 23, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Calcogenidos de arilstibinideno cristalinos: congéneres más pesados de los compuestos nitrosos aromáticos

Xinyi Li¹, Yizhen Chen¹, Shicheng Dong²

¹Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, Guangdong Basic Research Center of Excellence for Functional Molecular Engineering, School of Chemistry, IGCME, Sun Yat-sen University, Guangzhou 510275, China.

Journal of the American Chemical Society

|March 10, 2025

Resumen

Los investigadores aislaron y caracterizaron los calogenuros de arilstibinideno, los primeros congéneres más pesados de los compuestos nitrosos aromáticos. Estos compuestos estables presentan enlaces dobles antimonio-calcógeno no perturbados y exhiben una reactividad versátil en la síntesis.

Área de la Ciencia:

Química inorgánica
Química organometálica
Química sintética

Sus antecedentes:

Los compuestos nitroso (R-NO) son vitales en la síntesis orgánica.
Los calogenuros de pnictinideno más pesados (R-Pn=E) suelen ser muy reactivos y escasos.
La estabilización a menudo requiere la coordinación ácido/base de Lewis o efectos de resonancia.

Objetivo del estudio:

Aislar y caracterizar los nuevos congéneres más pesados de los compuestos nitroso aromáticos.
Investigar la estabilidad y las propiedades electrónicas de los calcogenuros de pnictinideno.
Para explorar la reactividad de estos compuestos recién sintetizados.

Principales métodos:

Síntesis a través de las reacciones de metástasis de sal.
Utilizando arildiclorostibanos y calogenuros de dilitio.
Caracterización mediante técnicas espectroscópicas y analíticas.

Principales resultados:

Aislamiento y caracterización exitosos de los calogenuros de arilstibinideno (SbE, E = S, Se, Te).
Demostración de enlaces dobles SbE no perturbados debido a una superposición orbital deficiente.
Observación de la reactividad versátil, incluida la transferencia de átomos de calcógeno y las reacciones de cicloadición.

Conclusiones:

Los calcogenuros de arilstibinideno representan los primeros congéneres estables más pesados de los compuestos nitrosos aromáticos.
Estos compuestos poseen estructuras electrónicas únicas que permiten una nueva reactividad.
Ofrecen potencial como nuevos reactivos en la química sintética.

Más Videos Relacionados

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV

Published on: December 29, 2016

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Videos de Conceptos Relacionados

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

Nucleophilic Aromatic Substitution: Addition–Elimination (S_NAr)

Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...

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,...

meta-Directing Deactivators: –NO2, –CN, –CHO, –&NoBreak;CO2R, –COR, –CO2H

meta-Directing Deactivators: –NO₂, –CN, –CHO, –⁠CO₂R, –COR, –CO₂H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...

Five-Membered Heterocyclic Aromatic Compounds: Overview

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...