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

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Maroto, Enrique E.
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Mateos, Jaime
orcId Garcia Borràs, Marc​ researcherId Garcia Borràs, Marc​ scopusId Garcia Borràs, Marc​ ​
Garcia Borràs, Marc
orcId Osuna Oliveras, Sílvia​ researcherId Osuna Oliveras, Sílvia​ scopusId Osuna Oliveras, Sílvia​ ​
Osuna Oliveras, Sílvia
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Filippone, Salvatore
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Herranz, María Ángeles
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Murata, Yasujiro
orcId Solà i Puig, Miquel​ researcherId Solà i Puig, Miquel​ scopusId Solà i Puig, Miquel​ ​
Solà i Puig, Miquel
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Martín, Nazario
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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 ​
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