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Alkyl Halides

Alkyl Halides

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...

Hydrogen Bonds

Hydrogen Bonds

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...

Hydrogen Bonds

Hydrogen Bonds

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....

Formation of Halohydrin from Alkenes

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

Aqueous Solutions and Heats of Hydration

Aqueous Solutions and Heats of Hydration

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...

Halogens

Halogens

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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Home
Probing Weak Halogen Bonding In Aqueous Solution.

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Probing Weak Halogen Bonding In Aqueous Solution.

Related Experiment Video

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Probing Weak Halogen Bonding in Aqueous Solution.

Manuel A Herbst¹, Leyun Wu^1,2, Yannik T Woordes¹

¹Department of Chemistry for Life Sciences, Uppsala University, Uppsala SE-751 23, Sweden.

Journal of the American Chemical Society

|April 28, 2026

View abstract on PubMed

Summary

This summary is machine-generated.

This study introduces a new NMR spectroscopy method to characterize weak halogen bonds in water. This technique allows for the detailed analysis of these crucial noncovalent interactions in biologically relevant solutions.

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Area of Science:

Chemical Physics
Biophysical Chemistry
Structural Biology

Background:

Noncovalent interactions are fundamental to chemistry and biology, dictating molecular structure, binding affinities, and reaction mechanisms.
Characterizing weak noncovalent forces, like halogen bonds, in aqueous solutions is challenging due to competing solvent interactions.
Weak interactions are critical in biological processes and drug discovery, necessitating robust analytical methods.

Purpose of the Study:

To develop and demonstrate a strategy for characterizing weak noncovalent interactions, specifically halogen bonding, in dilute aqueous solution.
To quantify the relative strength and geometry of iodine- and bromine-centered halogen bonds using NMR spectroscopy.
To provide a versatile methodology for assessing various weak interactions in biologically relevant solvents.

Main Methods:

Utilized Nuclear Magnetic Resonance (NMR) spectroscopy, including NOE- and J-coupling-based ensemble analysis, to quantify the population of a stabilized β-hairpin motif.
Employed 1H-13C residual dipolar couplings to determine the geometry and orientation of halogen bonds.
Corroborated experimental findings with Density Functional Theory (DFT) calculations.

Main Results:

Successfully characterized the relative strengths of weak halogen bonds involving iodine and bromine.
Determined the geometric parameters of halogen bonds in aqueous solution.
Demonstrated the stabilization effect of halogen bonds on a β-hairpin motif.

Conclusions:

Presented a novel NMR-based strategy for the detailed experimental characterization of halogen bonding in aqueous solution.
The methodology is transferable for assessing other weak noncovalent interactions in water, crucial for drug discovery.
This work provides a foundation for understanding and manipulating weak interactions in biological systems.