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Preparation of Binary and Ternary Deep Eutectic Systems
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Doubly ionic hydrogen bond interactions within the choline chloride-urea deep eutectic solvent.

Claire R Ashworth1, Richard P Matthews, Tom Welton

  • 1Department of Chemistry, Imperial College London, London, SW7 2AZ, UK. p.hunt@imperial.ac.uk.

Physical Chemistry Chemical Physics : PCCP
|June 23, 2016
PubMed
Summary
This summary is machine-generated.

Deep eutectic solvents (DESs) form diverse hydrogen bonds, including novel doubly ionic CHCl bonds with significant covalency. These interactions influence system entropy and eutectic formation, challenging existing models of DES structure.

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Area of Science:

  • Supramolecular Chemistry
  • Physical Chemistry
  • Materials Science

Background:

  • Deep eutectic solvents (DESs) are versatile solvent systems capable of forming various hydrogen bond types.
  • Understanding the intricate hydrogen bonding networks within DESs is crucial for predicting their properties and applications.
  • The choline chloride-urea system is a widely studied DES, often characterized by specific anionic complex formation.

Purpose of the Study:

  • To investigate the pairwise interactions between the components of the choline chloride-urea DES.
  • To identify and characterize the types and strengths of hydrogen bonds present in this DES.
  • To explore the implications of these hydrogen bonding interactions on the DES's structure and eutectic behavior.

Main Methods:

  • Computational examination of pairwise interactions within the choline chloride-urea system.
  • Analysis of hydrogen bond motifs, including neutral, ionic, and doubly ionic types.
  • Evaluation of the energetic contributions and covalency of identified hydrogen bonds.

Main Results:

  • Identification of a tripodal CHCl doubly ionic hydrogen bond motif.
  • Demonstration that doubly ionic hydrogen bonds can exhibit high covalency, comparable to or exceeding neutral and ionic bonds.
  • Observation of a wide array of hydrogen bond types ('alphabet soup') with flexible strengths and numbers.
  • Discovery of energetically competitive urea[choline](+) complexed cations alongside the previously proposed [Cl(urea)2](-) anions.
  • The urea[choline](+) cation forms the strongest hydrogen bond observed in the study.

Conclusions:

  • The hydrogen bonding landscape in choline chloride-urea DES is complex and diverse, featuring novel motifs like tripodal CHCl bonds.
  • Hydrogen bonding significantly impacts system entropy and plays a key role in eutectic formation.
  • The formation of urea[choline](+) cations is energetically competitive with [Cl(urea)2](-) anions, suggesting a more nuanced understanding of DES ion pairing is needed.