Video Experimental Relacionado

Updated: Apr 5, 2026

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

A Nitreno tiofosforílico singleto y su interconversión con los isómeros tiazil y tionitroso

Hongmin Li¹, Zhuang Wu¹, Dingqing Li¹

¹College of Chemistry, Chemical Engineering and Materials Science, Soochow University , Suzhou 215123, China.

Journal of the American Chemical Society

|August 16, 2015

Resumen

Los investigadores identificaron espectroscópicamente el tiofosforil nitreno más simple, F2P(S) N, en las matrices de gases nobles. Este intermediario reactivo se convierte en isómeros de tionitroso y tiazil tras la irradiación.

Área de la Ciencia:

Química inorgánica
La fotoquímica
Espectroscopia

Sus antecedentes:

Los tiofosforil-nitrenos (R2P(S) son productos intermedios reactivos que hasta ahora sólo se habían deducido a través de productos de captura.
Su estructura química y reactividad únicas permanecen en gran medida sin caracterizar debido a la inestabilidad.

Objetivo del estudio:

Para lograr la primera identificación espectroscópica directa de un tiofosforil nitreno.
Investigar las transformaciones fotoquímicas de los tiofosforil nitrenos y sus isómeros.

Principales métodos:

Fotólisis del tiofosforil azido (F2P(S) sustituido por el flúor en matrices sólidas de gases nobles.
Espectroscopia infrarroja (IR) y ultravioleta visible (UV-vis) para la caracterización.
Experimentos de irradiación con luz visible (≥495 nm) y luz UV (365 nm).
Pirólisis en el vacío de F2P(S) N3 para estudios en fase gaseosa.

Principales resultados:

Identificación espectroscópica del estado básico de los singlet del tiofosforil nitreno F2P(S) N.
La irradiación de luz visible indujo la isomerización al isómero tionitroso F2P-NS.
La irradiación con luz UV de F2P-NS condujo a la reformación de F2P(S) N e isomerización a la especie tiazil F2P-SN.
El isómero de tionitroso F2P-NS también se produjo mediante pirólisis de vacío flash en fase gaseosa.

Conclusiones:

Las pruebas espectroscópicas directas confirman la existencia y la estructura del tiofosforil nitreno F2P(S) N.
Las vías fotoquímicas revelan la interconversión entre las especies de nitreno, tionitroso y tiazil.
Este estudio proporciona información fundamental sobre la química de los compuestos de fósforo, nitrógeno y azufre.

Más Videos Relacionados

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

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

Videos de Conceptos Relacionados

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.

Nitrosation of Enols

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

SN2 Reaction: Stereochemistry

S_N2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...

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...