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

doi:10.1002/ejoc.201600912

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

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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 language	English
Pages (from-to)	4473-4475
Number of pages	3
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	26
DOIs	https://doi.org/10.1002/ejoc.201600912
Publication status	Published - 1 Sept 2016

Bibliographical note

Keywords

Anions
Electrophilic substitution
Pi complexes
Quantum mechanics
Structure elucidation

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10.1002/ejoc.201600912

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© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 'Authors unable or unwilling to pay the fees associated with OnlineOpen may make the accepted and peer-reviewed (but not final) version of their accepted article available on their personal website, in their company/institutional repository or archive, and in certain not-for-profit subject-based repositories, such as PubMed Central, subject to an embargo period of 12 months following publication of the version of record online'. (http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1099-0690/homepage/2046_onlineopen.html)
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Cite this

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title = "The π Complex of the Hydronium Ion Frozen on the Pathway of Electrophilic Aromatic Substitution",

abstract = "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.",

keywords = "Anions, Electrophilic substitution, Pi complexes, Quantum mechanics, Structure elucidation",

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note = "{\textcopyright} 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

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doi = "10.1002/ejoc.201600912",

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AU - Růžičková, Zdeňka

AU - Holub, Josef

AU - Melichar, Petr

AU - Moncol, Jan

AU - Wann, Derek A.

AU - Fanfrlík, Jindřich

AU - Růžička, Aleš

AU - Hnyk, Drahomír

PY - 2016/9/1

Y1 - 2016/9/1

N2 - 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.

AB - 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.

KW - Anions

KW - Electrophilic substitution

KW - Pi complexes

KW - Quantum mechanics

KW - Structure elucidation

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U2 - 10.1002/ejoc.201600912

DO - 10.1002/ejoc.201600912

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SN - 1434-193X

VL - 2016

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EP - 4475

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 26

ER -

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

Abstract

Bibliographical note

Keywords

Access to Document

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TRED: Towards molecular movies:exploring reaction dynamics using electron diffraction

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

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Projects

TRED: Towards molecular movies:exploring reaction dynamics using electron diffraction

Cite this