Effect of incarcerated HF on the exohedral chemical reactivity of HF@C60

Sara Vidal; Marta Izquierdo; Shamim Alom; Marc Garcia-Borràs; Salvatore Filippone; Sílvia Osuna; Miquel Solà; Richard J. Whitby; Nazario Martín

doi:10.1039/C7CC05987F

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Effect of incarcerated HF on the exohedral chemical reactivity of HF@C₆₀†

Sara Vidal,

^a Marta Izquierdo,

^a Shamim Alom,^b Marc Garcia-Borràs,

^cd Salvatore Filippone,

^a Sílvia Osuna,

^c Miquel Solà,

*^c Richard J. Whitby

*^b and Nazario Martín

*^ae

Author affiliations

* Corresponding authors

^a Dep. Química Orgánica I, UCM, Avda. Complutense s/n, E-28040 Madrid, Spain
E-mail: nazmar@ucm.es

^b Chemistry, University of Southampton, Southampton, UK
E-mail: r.j.whitby@soton.ac.uk

^c Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, c/Maria Aurèlia Capmany 6, 17003 Girona, Spain
E-mail: miquel.sola@udg.edu

^d Dep. of Chemistry and Biochemistry, University of California Los Angeles, 607 Charles E Young Drive East, CA90095 LA, USA

^e IMDEA–Nanociencia, C/Faraday, 9, Campus de Cantoblanco, E-28049 Madrid, Spain

Abstract

The first chemical modification on the brand new endohedral HF@C₆₀ is reported. In particular, the isomerization from optically pure (2S,5S)-cis-pyrrolidino[3,4:1,2][60]fullerene 2b to (2S,5R)-trans-pyrrolidino[3,4:1,2][60]fullerene 2b has been studied and compared with empty C₆₀ (2a) and endohedral H₂O@C₆₀ (3). The comparative study shows a kinetic order for the isomerization process of H₂O@C₆₀ > HF@C₆₀ > C₆₀, thus confirming the effect of the incarcerated species on the zwitterionic intermediate stability.

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Article information

DOI: https://doi.org/10.1039/C7CC05987F
Article type: Communication
Submitted: 01 Aug 2017
Accepted: 18 Aug 2017
First published: 18 Aug 2017

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Chem. Commun., 2017,53, 10993-10996

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Effect of incarcerated HF on the exohedral chemical reactivity of HF@C₆₀

S. Vidal, M. Izquierdo, S. Alom, M. Garcia-Borràs, S. Filippone, S. Osuna, M. Solà, R. J. Whitby and N. Martín, Chem. Commun., 2017, 53, 10993 DOI: 10.1039/C7CC05987F

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