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  The Interaction Modes of Haloimidazolium Salts in Solution

Schulz, N., Sokkar, P., Engelage, E., Schindler, S., Erdelyi, M., Sanchez-Garcia, E., et al. (2018). The Interaction Modes of Haloimidazolium Salts in Solution. Chemistry – A European Journal, 24(14), 3464-3473. doi:10.1002/chem.201705032.

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 Creators:
Schulz, Nils1, Author
Sokkar, Pandian2, 3, Author              
Engelage, Elric1, Author
Schindler, Severin1, Author
Erdelyi, Mate4, Author
Sanchez-Garcia, Elsa2, 3, Author              
Huber, Stefan1, Author
Affiliations:
1Department of Chemistry and Biochemistry, Ruhr-University-Bochum, Bochum, Germany, ou_persistent22              
2Department of Biology, Universität Duisburg-Essen, Essen, Germany, ou_persistent22              
3Research Group Sánchez-García, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1950289              
4Department of Chemistry and Molecular Biology and the Swedish NMR Centre, University of Gothenburg, Göteborg, Sweden, ou_persistent22              

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Free keywords: halogen bonding; hydrgen bonding; ion exchange; ion pairs; non-covalent interactions
 Abstract: We performed a comparative study on the interaction modes of 2‐haloimidazolium salts with anions in solution, particularly with regard to halogen bonding, hydrogen bonding and anion–π interactions. The syntheses and solid‐state analyses of a series of sterically and electronically modified 2‐haloimidazolium structures are presented. Detailed isothermal titration calorimetry (ITC) measurements, quantum mechanics/molecular mechanics (QM/MM), classical molecular dynamics simulations (MD) and free‐energy calculations together with NMR spectroscopy were used to elucidate the binding modes in solution. Our work reveals the absence of a potential anion–π interaction between the cationic imidazolium ring and the Lewis basic counteranion, and corroborates a formation of halogen bonding via the Lewis acidic iodine moiety and hydrogen bonding via the backbone hydrogen atoms, with repercussions in the field of organocatalysis.

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Language(s): eng - English
 Dates: 2017-10-232017-11-212018-03-07
 Publication Status: Published online
 Pages: 10
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201705032
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 24 (14) Sequence Number: - Start / End Page: 3464 - 3473 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058