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Related Concept Videos

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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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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Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Alkyl Halides02:45

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Structural Properties
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Halogen Bonding in Solution: Under Pressure.

Saber Mehrparvar1, Marcel Klinksiek2, Richard M Gauld1

  • 1Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum Universitätsstraβe 150, 44801 Bochum, Germany.

Journal of the American Chemical Society
|August 7, 2025
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Summary
This summary is machine-generated.

High pressure NMR titrations reveal that solvent choice significantly impacts organic halogen bonding. While some Lewis bases strengthen binding under pressure, others unexpectedly weaken, highlighting solvent effects in supramolecular chemistry.

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Area of Science:

  • Supramolecular Chemistry
  • Physical Organic Chemistry
  • Chemical Thermodynamics

Background:

  • Halogen bonding is a crucial non-covalent interaction in supramolecular chemistry.
  • Understanding the influence of external conditions like pressure on these interactions is vital for controlling molecular assembly.
  • Previous studies have largely focused on halogen bonding in the gas phase or solid state, with limited data in solution.

Purpose of the Study:

  • To investigate the effect of high pressure on organic halogen bond donors in various solution environments.
  • To explore the role of different Lewis bases (orthoamides, halides, thiourea) in pressure-dependent halogen bonding.
  • To provide a foundation for the rational application of high pressure in solution-based halogen bonding.

Main Methods:

  • High-pressure Nuclear Magnetic Resonance (HP-NMR) titrations were employed.
  • Experiments were conducted in multiple solvents including CDCl3, CD2Cl2, acetone-d6, and THF-d8.
  • Thermodynamic modeling using the Perturbed-Chain Statistical Associating Fluid Theory (PC-SAFT) was utilized for data analysis.

Main Results:

  • A neutral tridentate halogen bond donor exhibited pressure-enhanced binding with an orthoamide in tested solvents.
  • Halides unexpectedly showed decreased association constants with the donor in CDCl3, CD2Cl2, and acetone-d6.
  • Bromide binding with a thiourea (hydrogen bond donor) weakened at elevated pressure, contrasting with orthoamide behavior.

Conclusions:

  • Solvent effects play a critical role in modulating the strength of halogen-bonded complexes, particularly those involving charged species.
  • High pressure can be a powerful tool to tune halogen bond interactions in solution, offering new avenues for supramolecular design.
  • The findings necessitate careful consideration of solvent choice and pressure conditions for optimizing halogen bonding applications.