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Solution, Solubility, and Solubility Equilibrium
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In acid-base chemistry, the leveling effect refers to the limitation imposed by the solvent on the strength of acids and bases in solution. When a base stronger than the solvent's conjugate base is used, it deprotonates the solvent until the base is entirely consumed, making it ineffective against weaker acids. Conversely, an acid stronger than the solvent's conjugate acid protonates the solvent until the acid is depleted, rendering it ineffective against weaker bases. Essentially, the...
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Dissecting Solvent Effects on Hydrogen Bonding.

Nicole Y Meredith1, Stefan Borsley1, Ivan V Smolyar1

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh, EH9 3FJ, UK.

Angewandte Chemie (International Ed. in English)
|May 24, 2022
PubMed
Summary
This summary is machine-generated.

Researchers quantified hydrogen bond energetics in solvents using molecular balances. Empirical dissection of solvent effects improved correlations between computed and experimental data, revealing secondary interaction energetics.

Keywords:
Electrostatic InteractionsHydrogen BondsNoncovalent InteractionsSolvent Effects

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Area of Science:

  • Chemical Physics
  • Computational Chemistry
  • Supramolecular Chemistry

Background:

  • Isolating hydrogen bond (H-bond) energetics from solvent effects is experimentally difficult.
  • Understanding H-bond interactions is crucial in chemistry and biology.

Purpose of the Study:

  • To quantify amine/amide H-bond energetics in various solvents.
  • To establish reliable correlations between experimental and computational H-bond data.
  • To investigate the influence of solvent effects on H-bond energetics.

Main Methods:

  • Utilized synthetic molecular balances to measure H-bond interactions.
  • Determined over 200 conformational free energy differences using 24 H-bonding balances.
  • Employed Hunter's α/β solvation model for empirical dissection of solvent effects.

Main Results:

  • Observed significant solvent-dependent variations in correlations between experimental and gas-phase computed energies.
  • Achieved excellent correlations after applying empirical dissection of solvent effects.
  • Identified energetics of secondary interactions, like competing H-bonds, through fitted constants.

Conclusions:

  • Empirical dissection of solvent effects is vital for accurate comparison of experimental and computational H-bond data.
  • The molecular balance method provides a robust approach to quantify H-bond energetics.
  • This study offers insights into the complex interplay of H-bonds and solvation.