Electric field catalyzed
Diels-Alder reaction
of C70 with cyclohexa-1,3-diene
Vojtˇech Šádek, Cina Foroutan-Nejad
Faculty of Science, Masaryk University, Kamenice 5A4, 62500 Brno, Czech Republic
150981@mail.muni.cz
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Reaction 1: Diels-Alder reaction of C70 with cyclohexa-1,3-diene with list of reasonable regioisomers of product. Double
bonds are not marked.
C70 is a fullerene with prolonged ellipsoidal shape and D5h symmetry. The structure consist of
eight distinct groups of C-C bonds. Three of them have enough double bond character, so that
they may react in Diels-Alder reaction. Reaction with cyclohexa-1,3-diene serves as the simplest
meaningful model of anchoring C70 onto graphite sheet.
The influence of uniform external electric field (EEF) on the energetics of reaction 1 is studied
by DFT methods on B97D3/Def2SVP level of theory. Reaction kinetics are analyzed through
master equation implemented in Multiwell software[1].
The EEF affects the reactions towards three products differently, which may be used for
improving stereoselectivity.
References
[1] J. R. Barker, T. L. Nguyen, J. F. Stanton, C. Aieta, M. Ceotto, F. Gabas, T. J. D. Kumar, C. G. L.
Li, L. L. Lohr, A. Maranzana, N. F. Ortiz, J. M. Preses, J. M. Simmie, J. A. Sonk, P. J. Stimac,
MultiWell-2017 Software Suite, http://clasp-research.engin.umich.edu/multiwell/,
2017.
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