2026-04-19T19:16:01Zhttps://recercat.cat/oai/request

oai:recercat.cat:10256/103582024-06-18T13:49:00Zcom_2072_452955com_2072_2054col_2072_453073

Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60 Maroto, Enrique E. Mateos, Jaime Garcia Borràs, Marc Osuna Oliveras, Sílvia Filippone, Salvatore Herranz, María Ángeles Murata, Yasujiro Solà i Puig, Miquel Martín, Nazario Ful·lerens Fullerenes Isomerització Isomerization 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 Financial support by the European Research Council (ERC-320441-Chirallcarbon and FP7-PEOPLE-2013-CIG-630978 to S.O.), the Ministerio de Economia y Competitividad (MINECO) of Spain (projects CTQ2011-24652/BQU and CTQ2011-23156/BQU, JdlC contract to S.O, and AP2010-2517 to M.G.-B.), the CAM (PHOTOCARBON project S2013/MIT-2841), the Generalitat de Catalunya (project number 2014SGR931 and ICREA Academia 2009 to M.S.) is acknowledged. N.M. thanks to the Alexander von Humboldt Foundation 2024-06-18T13:49:00Z 2024-06-18T13:49:00Z 2024-06-18T13:49:00Z info:eu-repo/date/embargoEnd/2026-01-01 info:eu-repo/date/embargoEnd/2026-01-01 2015 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://hdl.handle.net/10256/10358 info:eu-repo/semantics/altIdentifier/doi/10.1021/ja5108854 info:eu-repo/semantics/altIdentifier/issn/0002-7863 info:eu-repo/semantics/altIdentifier/eissn/1520-5126 info:eu-repo/grantAgreement/MICINN//CTQ2011-23156/ES/AVANCES EN CATALISIS Y AROMATICIDAD/ AGAUR/2014-2016/2014 SGR-931 info:eu-repo/grantAgreement/EC/FP7/630978/EU/Computational Exploration of Directed Evolution rules for tuning enzymatic activities/DIREVENZYME info:eu-repo/grantAgreement/EC/FP7/320441/EU/Chiral Allotropes of Carbon/CHIRALLCARBON Tots els drets reservats info:eu-repo/semantics/embargoedAccess American Chemical Society (ACS) © Journal of the American Chemical Society, 2015, vol. 137, núm. 3, p. 1190-1197 Articles publicats (D-Q)