Inversion and rotation processes involving non-planar aromatic compounds catalyzed by extended polycyclic aromatic hydrocarbons

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Abstract

© 2014 Elsevier B.V. All rights reserved. Using accurate quantum chemical calculations, we show that extended planar polycyclic aromatic hydrocarbons (PAHs) can efficiently catalyze a range of chemical processes involving non-planar aromatic systems. These include (i) bowl-to-bowl inversion of curved PAHs (e.g. corannulene and sumanene), (ii) 'flip-flop' inversion of helicenes (e.g. benzo[c]phenanthrene), and (iii) rotation about the PhPh bond in biphenyls. Non-covalent π-π interactions between the planar catalyst and the substrate stabilize the planar transition structures to a greater extent than they stabilize the non-planar reactants. These result in surprisingly large catalytic enhancements (namely, the reaction barrier heights are reduced by 21-63% of the uncatalyzed reaction barriers).
Original languageEnglish
Pages (from-to)156-161
Number of pages6
JournalChemical Physics Letters
Volume614
Early online date18 Sep 2014
DOIs
Publication statusPublished - 20 Oct 2014

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