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Radical Halogenation: Thermodynamics

Radical Halogenation: Thermodynamics

The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy between bonds broken and bonds...

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.

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.

Enthalpy of Solution

Enthalpy of Solution

There are two criteria that favor, but do not guarantee, the spontaneous formation of a solution:

Bond Energies and Bond Lengths

Bond Energies and Bond Lengths

Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, that is, the energy necessary to separate the bonded atoms. Separating any pair of bonded atoms requires energy — the stronger a bond, the greater the energy required to break it.

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Related Experiment Video

Updated: May 19, 2026

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

Halogen bonding in solution: thermodynamics and applications.

Thomas M Beale¹, Michael G Chudzinski, Mohammed G Sarwar

¹Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, M5S 3H8, Canada.

Chemical Society Reviews

|August 4, 2012

Summary

This summary is machine-generated.

Halogen bonding, a key interaction in solids, is now proven effective in solution. This review covers six decades of data showing its use in molecular recognition, drug design, and catalysis.

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Last Updated: May 19, 2026

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Published on: February 15, 2016

Area of Science:

Chemistry
Physical Chemistry
Supramolecular Chemistry

Background:

Halogen bonds are noncovalent interactions where bound halogens act as electrophiles.
Their utility in solid-state self-assembly is well-established in crystal engineering and materials science.
The role of halogen bonding in the solution phase remained less understood until recently.

Purpose of the Study:

To review and interpret solution-phase thermodynamic data for halogen bonding over the past 60 years.
To highlight the growing applications of halogen bonding in solution.
To provide a comprehensive overview for researchers in the field.

Main Methods:

Compilation and analysis of solution-phase thermodynamic data.
Interpretation of data to understand halogen bond strength and behavior.
Literature review of emerging applications.

Main Results:

Thermodynamic data confirm the significance of halogen bonding in solution.
Halogen bonding influences conformation, binding, and reactivity in solution.
Emerging applications demonstrate practical utility beyond the solid state.

Conclusions:

Halogen bonding is a versatile interaction applicable in both solid and solution phases.
The understanding of solution-phase halogen bonding has significantly advanced.
This interaction holds great promise for molecular recognition, medicinal chemistry, and catalysis.