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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


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.

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

Bibliographical note

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


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

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