title: Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: hydrogen-bonding assistance in the carbanion stabilization in H2O@C60.
abstract: 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 findings. 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.
authors.affiliation: Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense , E-28040 Madrid, Spain.
authors.forename: Enrique E
authors.initials: EE
authors.lastname: Maroto
authors.forename: Jaime
authors.initials: J
authors.lastname: Mateos
authors.forename: Marc
authors.initials: M
authors.lastname: Garcia-Borràs
authors.forename: Sílvia
authors.initials: S
authors.lastname: Osuna
authors.forename: Salvatore
authors.initials: S
authors.lastname: Filippone
authors.forename: María Ángeles
authors.initials: MÁ
authors.lastname: Herranz
authors.forename: Yasujiro
authors.initials: Y
authors.lastname: Murata
authors.forename: Miquel
authors.initials: M
authors.lastname: Solà
authors.forename: Nazario
authors.initials: N
authors.lastname: Martín