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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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Intermolecular vs Intramolecular Forces03:00

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Intermolecular forces (IMF) are electrostatic attractions arising from charge-charge interactions between molecules. The strength of the intermolecular force is influenced by the distance of separation between molecules. The forces significantly affect the interactions in solids and liquids, where the molecules are close together. In gases, IMFs become important only under high-pressure conditions (due to the proximity of gas molecules). Intermolecular forces dictate the physical properties of...
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Hydrogen Bonds01:04

Hydrogen Bonds

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A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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Hydrogen Bonds00:26

Hydrogen Bonds

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Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
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Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
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Comparing Intermolecular Forces: Melting Point, Boiling Point, and Miscibility02:34

Comparing Intermolecular Forces: Melting Point, Boiling Point, and Miscibility

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Intermolecular forces are attractive forces that exist between molecules. They dictate several bulk properties, such as melting points, boiling points, and solubilities (miscibilities) of substances. Molar mass, molecular shape, and polarity affect the strength of different intermolecular forces, which influence the magnitude of physical properties across a family of molecules.
Temporary attractive forces like dispersion are present in all molecules, whether they are polar or nonpolar. They...
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Competing intramolecular vs. intermolecular hydrogen bonds in solution.

Peter I Nagy1

  • 1Center for Drug Design and Development, the University of Toledo, Toledo, OH 43606-3390, USA. pnagy@utnet.utoledo.edu.

International Journal of Molecular Sciences
|October 30, 2014
PubMed
Summary

This review explores how solvent interactions influence molecular conformations, specifically the competition between intramolecular and intermolecular hydrogen bonds in organic molecules. It highlights how solution environments dictate structural stability over gas-phase preferences.

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Area of Science:

  • Physical Chemistry
  • Computational Chemistry
  • Organic Chemistry

Background:

  • Hydrogen bonds are crucial for molecular structure, definable by IUPAC or atoms-in-molecules theory.
  • Structural conformations can be influenced by electrostatic interactions beyond hydrogen bonding.
  • Small organic molecules exhibit conformational preferences influenced by intramolecular vs. intermolecular hydrogen bonds in solution.

Purpose of the Study:

  • To review the competition between intramolecular and intermolecular hydrogen bonds in small organic molecules in solution.
  • To analyze how solvent effects alter molecular conformations.
  • To survey solvent effects on dimeric systems and acid-base complexes.

Main Methods:

  • Literature review of studies on hydrogen bonding and molecular conformations.
  • Analysis of theoretical definitions of hydrogen bonds (IUPAC, atoms-in-molecules).
  • Consideration of molecular dynamics simulations and potential of mean force curves for solvent effects.

Main Results:

  • Intramolecular hydrogen bonds stable in gas-phase can disrupt in protic solutions.
  • Solute-solvent interactions can favor intermolecular hydrogen bonds over intramolecular ones.
  • Solvent effects influence the stability of dimeric systems and the type (neutral/ionic) of intermolecular hydrogen bonds in acid-base complexes.

Conclusions:

  • The balance between internal energy and solute-solvent interactions dictates liquid-phase conformer composition.
  • Solvent choice significantly impacts molecular conformation and hydrogen bonding patterns.
  • Understanding solvent effects is critical for predicting molecular behavior in solution.