Maroto, EnriqueMateos, JaimeGarcía Borràs, MarcOsuna, SilviaFilippone, SalvatoreHerranz, M.AngelesMurata, YasujiroSolà, MiquelMartín, Nazario2023-06-192023-06-192015-011520-512610.1021/ja5108854https://hdl.handle.net/20.500.14352/35074The 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.engjournal articlehttp://pubs.acs.org/doi/pdf/10.1021/ja5108854open access547HydrogenHydrogen bondsIsomersMoleculesStabilizationStereochemistry Cis-trans IsomerizationComputational calculationsDFT calculationElectronic naturesEndo-fullerenesFulleropyrrolidinesReaction mechanismRearrangement processQuímica orgánica (Química)2306 Química Orgánica