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Related Concept Videos

Hydrogen Bonds01:04

Hydrogen Bonds

15.4K
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.
Hydrogen Bonds Control the World!
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

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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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Molecular Shape and Polarity03:37

Molecular Shape and Polarity

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Dipole Moment of a Molecule
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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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Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Hydrogen bonding vs. halogen bonding: the solvent decides.

Craig C Robertson1, James S Wright1, Elliot J Carrington1

  • 1Department of Chemistry , University of Sheffield , Brook Hill , Sheffield , S3 7HF , UK .

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Summary

Solvent polarity controls the self-assembly of co-crystals by directing competition between hydrogen bonds and halogen bonds. Less polar solvents favor hydrogen bonds, while more polar solvents favor halogen bonds.

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Area of Science:

  • Supramolecular Chemistry
  • Crystallography
  • Materials Science

Background:

  • Controlling intermolecular interactions is key to understanding and utilizing self-assembly processes.
  • Hydrogen bonds and halogen bonds are fundamental directional intermolecular forces with distinct properties.
  • Co-crystal formation offers a route to engineer materials with desired properties.

Purpose of the Study:

  • To investigate the role of solvent polarity in directing the competitive self-assembly of co-crystals.
  • To determine how solvent choice influences the dominance of hydrogen bonds versus halogen bonds in co-crystal formation.
  • To explore the relationship between solvent effects and the relative strengths of competing intermolecular interactions.

Main Methods:

  • Investigated competitive co-crystal formation using three pairs of hydrogen bond and halogen bond donors with a common acceptor.
  • Examined co-crystal formation in seven different solvents with varying polarities.
  • Analyzed product formation and phase purity using powder X-ray diffraction (PXRD).

Main Results:

  • Hydrogen-bonded co-crystals were favored in less polar solvents.
  • Halogen-bonded co-crystals were favored in more polar solvents.
  • The switch in dominance from hydrogen to halogen bonds was dependent on relative interaction strengths and solvent polarity.

Conclusions:

  • Solvent polarity is a critical factor in controlling the self-assembly of co-crystals through competitive intermolecular interactions.
  • Understanding solvent effects is essential for precisely directing co-crystal formation and harnessing self-assembly.
  • The findings provide a framework for designing and synthesizing co-crystals with predictable structures and properties.