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The π Complex of the Hydronium Ion Frozen on the Pathway of Electrophilic Aromatic Substitution
Author(s) -
Růžičková Zdeňka,
Holub Josef,
Melichar Petr,
Moncol Jan,
Wann Derek A.,
Fanfrlík Jindřich,
Růžička Aleš,
Hnyk Drahomír
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600912
Subject(s) - chemistry , hydronium , toluene , protonation , electrophilic aromatic substitution , ion , crystal structure , crystal (programming language) , single crystal , electrophilic substitution , aromaticity , photochemistry , crystallography , medicinal chemistry , inorganic chemistry , organic chemistry , molecule , computer science , programming language
A very rare crystal was prepared consisting of a 2D aromatic (toluene) together with a weakly coordinating 3D aromatic ( closo ‐1‐CB 11 H 12 – ) 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.