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The π Complex of the Hydronium Ion Frozen on the Pathway of Electrophilic Aromatic Substitution

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  • Zdeňka Růžičková
  • Josef Holub
  • Petr Melichar
  • Jan Moncol
  • Derek A. Wann
  • Jindřich Fanfrlík
  • Aleš Růžička
  • Drahomír Hnyk


Publication details

JournalEuropean Journal of Organic Chemistry
DatePublished - 1 Sep 2016
Issue number26
Number of pages3
Pages (from-to)4473-4475
Original languageEnglish


A very rare crystal was prepared consisting of a 2D aromatic (toluene) together with a weakly coordinating 3D aromatic (closo-1-CB11H12 ) and a hydronium ion, and this crystal was analyzed by using X-ray diffraction and high-level quantum-mechanical calculations. The nature of the crystal arrangement made it possible to detect the frozen π complex that would originate during protonation of toluene by the acidic hydronium ion.

Bibliographical note

© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

    Research areas

  • Anions, Electrophilic substitution, Pi complexes, Quantum mechanics, Structure elucidation


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