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Enantiospecific cis−trans Isomerization in Chiral Fulleropyrrolidines:Hydrogen-Bonding Assistance in the Carbanion Stabilization in H2O@C60

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Maroto, Enrique and Mateos, Jaime and García Borràs, Marc and Osuna, Silvia and Filippone, Salvatore and Herranz, M.Angeles and Murata, Yasujiro and Solà, Miquel and Martín, Nazario (2015) Enantiospecific cis−trans Isomerization in Chiral Fulleropyrrolidines:Hydrogen-Bonding Assistance in the Carbanion Stabilization in H2O@C60. Journal of the American Chemical Society, 137 (3). pp. 1190-1197. ISSN 1520-5126

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Official URL: http://pubs.acs.org/doi/pdf/10.1021/ja5108854



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.


Item Type:Article
Uncontrolled Keywords:Hydrogen; Hydrogen bonds; Isomers; Molecules; Stabilization; Stereochemistry Cis-trans Isomerization; Computational calculations; DFT calculation; Electronic natures; Endo-fullerenes; Fulleropyrrolidines; Reaction mechanism; Rearrangement process
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:35970
Deposited On:26 Feb 2016 12:03
Last Modified:02 Mar 2016 12:57

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