Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60

The stereochemical outcome of cis-trans isomerization of optically pure [60], [70], and endohedral H2O@C60 fulleropyrrolidines reveals that the electronic nature of substituents, fullerene size, and surprisingly the incarcerated water molecule plays a crucial role in this rearrangement process. Theo...

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Detalles Bibliográficos
Autores: Maroto, Enrique E., Mateos, Jaime, Garcia Borràs, Marc, Osuna Oliveras, Sílvia, Filippone, Salvatore, Herranz, María Ángeles, Murata, Yasujiro, Solà i Puig, Miquel, Martín, Nazario
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/10358
Acceso en línea:http://hdl.handle.net/10256/10358
Access Level:acceso embargado
Palabra clave:Ful·lerens
Fullerenes
Isomerització
Isomerization
Descripción
Sumario:The stereochemical outcome of cis-trans isomerization of optically pure [60], [70], and endohedral H2O@C60 fulleropyrrolidines reveals that the electronic nature of substituents, fullerene size, and surprisingly the incarcerated water molecule plays a crucial role in this rearrangement process. Theoretical DFT calculations are in very good agreement with the experimental fi ndings. On the basis of the experimental results and computational calculations, a plausible reaction mechanism involving the hydrogen-bonding assistance of the inner water molecule in the carbanion stabilization of endofullerene is proposed