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Related Concept Videos

Intermolecular Forces03:13

Intermolecular Forces

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Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen...
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The reaction between a Brønsted-Lowry acid and water is called acid ionization. For example, when hydrogen fluoride dissolves in water and ionizes, protons are transferred from hydrogen fluoride molecules to water molecules, yielding hydronium ions and fluoride ions:
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Aqueous Solutions and Heats of Hydration02:42

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Water and other polar molecules are attracted to ions. The electrostatic attraction between an ion and a molecule with a dipole is called an ion-dipole attraction. These attractions play an important role in the dissolution of ionic compounds in water.
When ionic compounds dissolve in water, the ions in the solid separate and disperse uniformly throughout the solution because water molecules surround and solvate the ions, reducing the strong electrostatic forces between them. This process...
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Solubility Equilibria: Ionic Product of Water01:16

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Pure water is a weak electrolyte; only a small amount ionizes into hydrogen and hydroxide ions. At any given temperature, the concentration of undissociated water is almost constant, so the ionic product of water is the product of the hydrogen and hydroxide ion concentrations, denoted as Kw. The square root of Kw gives the individual ion concentrations.
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Van der Waals Interactions01:24

Van der Waals Interactions

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Atoms and molecules interact with each other through intermolecular forces. These electrostatic forces arise from attractive or repulsive interactions between particles with permanent, partial, or temporary charges. The intermolecular forces between neutral atoms and molecules are ion–dipole, dipole–dipole, and dispersion forces, collectively known as van der Waals forces.
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pH Scale02:41

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Hydronium and hydroxide ions are present both in pure water and in all aqueous solutions, and their concentrations are inversely proportional as determined by the ion product of water (Kw). The concentrations of these ions in a solution are often critical determinants of the solution’s properties and the chemical behaviors of its other solutes. Two different solutions can differ in their hydronium or hydroxide ion concentrations by a million, billion, or even trillion times. A common means of...
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Water and the Cation-π Interaction.

Yujie Zhu1, Minmin Tang1, Huibin Zhang1

  • 1Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science, Shanghai University, 99 Shang-Da Road, Shanghai 200444, China.

Journal of the American Chemical Society
|July 30, 2021
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Summary
This summary is machine-generated.

In water, synthetic containers bind more strongly to uncharged tert-butyl groups than to charged trimethylammonium groups. This highlights the significant impact of solvation on cation-π interactions in biological recognition.

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Area of Science:

  • Supramolecular Chemistry
  • Physical Chemistry
  • Biophysical Chemistry

Background:

  • Cation-π interactions and hydrophobic effects are crucial intermolecular forces governing molecular recognition in biological systems.
  • Understanding these forces is key to designing synthetic systems that mimic biological functions.
  • Previous studies have explored these interactions, but direct comparisons in aqueous environments are limited.

Purpose of the Study:

  • To directly compare the relative binding strengths of cation-π interactions and hydrophobic effects in water.
  • To investigate the role of solvation in modulating the strength of cation-π interactions.
  • To quantify the binding preferences of synthetic container hosts for different guest moieties.

Main Methods:

  • Utilized molecular "dumbbell" guests with competing trimethylammonium (cationic) and tert-butyl (hydrophobic) groups.
  • Employed synthetic container hosts with aromatic internal surfaces to bind the guests.
  • Studied binding in aqueous solutions to assess the influence of solvation effects.

Main Results:

  • Synthetic containers consistently demonstrated a preference for binding the uncharged tert-butyl groups over the cationic trimethylammonium groups.
  • The solvation of the polar trimethylammonium group in water was found to be a dominant factor, outweighing the cation-π attraction.
  • Binding to the tert-butyl group was over 12 kJ mol⁻¹ more favorable than cation-π interactions in these cavitand complexes.

Conclusions:

  • Solvation effects in water significantly diminish the strength of cation-π interactions compared to hydrophobic interactions.
  • Synthetic container complexes provide a valuable platform for quantitatively measuring the relative contributions of different intermolecular forces.
  • The findings offer insights into molecular recognition mechanisms in biological systems, emphasizing the importance of considering solvent effects.