The π Complex of the Hydronium Ion Frozen on the Pathway of Electrophilic Aromatic Substitution. Issue 26 (30th August 2016)

• Record Type: Journal Article
• Authors: Růžičková, Zdeňka; Holub, Josef; Melichar, Petr; Moncol, Jan; Wann, Derek A.; Fanfrlík, Jindřich; Růžička, Aleš; Hnyk, Drahomír
• Is Part Of: European journal of organic chemistry. Issue 26(2016)
• Page Start: 4473
• Page End: 4475
• Publication Date: 2016-08-30
• Subjects: Anions -- Pi complexes -- Electrophilic substitution -- Quantum mechanics -- Structure elucidation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600912
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A very rare crystal was prepared consisting of a 2D aromatic (toluene) together with a weakly coordinating 3D aromatic ( closo ‐1‐CB11 H12 – ) 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. Abstract : A ternary crystal that consists of a weakly coordinating and 3D aromatic anion (1‐CB11 H12 – ), hydronium (H3 O + ), and toluene is obtained, and its crystal‐packing forces are computationally analyzed. The presence of this anion enables the other two components of the crystal to be viewed as a frozen π complex that originates during proton exchange occurring at the 2D aromatic toluene.