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H-Bond donor parameters for cations.

Sarah J Pike1, Ennio Lavagnini1, Lisa M Varley2

  • 1Department of Chemistry , University of Cambridge , Lensfield Road , Cambridge , CB2 1EW , UK .

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|July 31, 2019
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Summary
This summary is machine-generated.

This study quantifies cation hydrogen-bonding abilities using transferable alpha parameters. These findings enable accurate prediction of cation recognition in diverse chemical environments.

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Area of Science:

  • Supramolecular Chemistry
  • Analytical Chemistry
  • Physical Chemistry

Background:

  • Understanding cation interactions with neutral hydrogen-bond acceptors is crucial in various chemical and biological systems.
  • Quantifying the hydrogen-bond donating strength of diverse cations is essential for predicting their behavior in solution.
  • Previous studies often lacked a unified parameter system for comparing different cation types across various environments.

Purpose of the Study:

  • To develop and validate a consistent set of hydrogen-bond donor (α) parameters for a wide range of organic and inorganic cations.
  • To investigate the transferability of these α parameters between different solvents (acetone, acetonitrile) and hydrogen-bond acceptors.
  • To assess the influence of water and counter-anions on cation complexation in polar organic solvents.

Main Methods:

  • UV/Vis absorption and Nuclear Magnetic Resonance (NMR) spectroscopy titrations were employed to study cation-acceptor complex formation.
  • Complexation was investigated for fifteen different cations with two distinct neutral hydrogen-bond acceptors.
  • Data analysis focused on determining self-consistent α parameters for each cation.

Main Results:

  • Self-consistent hydrogen-bond donor (α) parameters were successfully determined for guanidinium, various ammonium cations, imidazolium, methylpyridinium, and alkali metal cations (Li+, Na+, K+, Rb+, Cs+).
  • The determined α parameters demonstrated excellent transferability across different solvents and hydrogen-bond acceptor partners.
  • Lithium and protonated nitrogen cations exhibited the strongest hydrogen-bonding (α ≈ 5.0), while quaternary ammonium cations were the weakest (α ≈ 2.7). Alkali metal α parameters decreased down the group (Li+ to Cs+).

Conclusions:

  • The developed α parameter system provides a reliable method for predicting cation recognition properties in various chemical environments.
  • The transferability of α parameters simplifies the study and prediction of cation complexation behavior.
  • The findings offer valuable insights into the relative hydrogen-bonding strengths of diverse cations, aiding in molecular design and recognition studies.