Your browser doesn't support javascript.
loading
"The Sulfur Dance" Around Arenes and Heteroarenes - the Reversible Nature of Nucleophilic Aromatic Substitutions.
Gahlot, Sapna; Schmitt, Jean-Louis; Chevalier, Aline; Villa, Marco; Roy, Myriam; Ceroni, Paola; Lehn, Jean-Marie; Gingras, Marc.
Afiliación
  • Gahlot S; Aix Marseille Univ, CNRS, CINaM, 13288, Marseille, France.
  • Schmitt JL; Institut de Science et d'Ingénierie Supramoléculaires (ISIS), CNRS UMR 7006, Université de Strasbourg, 8 allée Gaspard Monge, BP 70028, 67083, Strasbourg Cedex, France.
  • Chevalier A; Institut de Science et d'Ingénierie Supramoléculaires (ISIS), CNRS UMR 7006, Université de Strasbourg, 8 allée Gaspard Monge, BP 70028, 67083, Strasbourg Cedex, France.
  • Villa M; Aix Marseille Univ, CNRS, CINaM, 13288, Marseille, France.
  • Roy M; Department of Chemistry ("Giacomo Ciamician"), University of Bologna, Via Selmi, 2, 40126, Bologna, Italy.
  • Ceroni P; Aix Marseille Univ, CNRS, CINaM, 13288, Marseille, France.
  • Lehn JM; Institut Parisien de Chimie Moléculaire, Sorbonne Université, 75005, Paris, France.
  • Gingras M; Department of Chemistry ("Giacomo Ciamician"), University of Bologna, Via Selmi, 2, 40126, Bologna, Italy.
Chemistry ; : e202400231, 2024 Jan 30.
Article en En | MEDLINE | ID: mdl-38289151
ABSTRACT
We disclose the features of a category of reversible nucleophilic aromatic substitutions in view of their significance and generality in dynamic aromatic chemistry. Exchange of sulfur components surrounding arenes and heteroarenes may occur at 25 °C, in a process that one may call a "sulfur dance". These SN Ar systems present their own features, apart from common reversible reactions utilized in dynamic covalent chemistry (DCC). By varying conditions, covalent dynamics may operate to provide libraries of thiaarenes with some selectivity, or conversion of a hexa(thio)benzene asterisk into another one. The reversible nature of SN Ar is confirmed by three

methods:

a convergence of the products distribution in reversible SN Ar systems, a related product redistribution between two per(thio)benzenes by using a thiolate promoter, and from kinetic/thermodynamic data. A four-component dynamic covalent system further illustrates the thermodynamically-driven formation of a thiacalix[2]arene[2]pyrimidine by sulfur component exchanges. This work stimulates the implementation of reversible SN Ar in aromatic chemistry and in DCC.
Palabras clave
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Alemania