The Interaction Modes of Haloimidazolium Salts in Solution (Note)
| Autor: | Nils Schulz, Máté Erdélyi, Elric Engelage, Elsa Sanchez-Garcia, Stefan M. Huber, Pandian Sokkar, Severin Schindler |
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| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Steric effects
chemistry.chemical_classification Halogen bond Hydrogen 010405 organic chemistry Hydrogen bond Organic Chemistry chemistry.chemical_element Isothermal titration calorimetry General Chemistry Nuclear magnetic resonance spectroscopy 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Molecular dynamics chemistry Computational chemistry Non-covalent interactions Biologie |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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