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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...

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Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

Hybridization of Atomic Orbitals I

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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...

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Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

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Updated: Oct 22, 2025

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

An expanded halogen bonding scale using astatine.

Lu Liu¹, Seyfeddine Rahali^2,3, Rémi Maurice¹

¹SUBATECH UMR 6457, CNRS, IMT Atlantique, Université de Nantes 4 Rue Alfred Kastler 44307 Nantes France julie.champion@subatech.in2p3.fr.

Chemical Science

|August 27, 2021

Summary

This summary is machine-generated.

We developed a new scale to measure halogen bond strength with astatine, the strongest halogen donor. This scale helps understand interactions and improve targeted radionuclide therapy by enhancing radiolabeling.

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Area of Science:

Chemistry
Supramolecular Chemistry
Radiochemistry

Background:

Halogen bonding is a crucial non-covalent interaction for controlling molecular recognition.
Quantifying halogen bond strength is essential for various scientific fields.
Astatine is the most potent halogen-bond donor element, yet its acceptor strength scale was lacking.

Purpose of the Study:

To establish the first experimental basicity scale for astatine halogen bonding (pKBAtI).
To quantify the halogen-bond acceptor strength of various Lewis bases towards astatine monoiodide (AtI).
To provide a thermodynamic basis for understanding astatine interactions.

Main Methods:

Complexation constants were measured between astatine monoiodide (AtI) and sixteen selected Lewis bases.
A thermodynamic approach was used to quantify halogen-bond acceptor strength.
The pKBAtI scale was established based on these measurements.

Main Results:

The pKBAtI scale spans over 6 log units, quantifying acceptor strength towards astatine.
N,N,N',N'-tetramethylthiourea showed the highest basicity (5.69 ± 0.32).
Sulfur-containing bases exhibited the highest AtI basicity, while carbon π-bases were the weakest acceptors.

Conclusions:

The pKBAtI scale provides a valuable tool for understanding and predicting astatine halogen bonding.
The scale reveals distinct trends in acceptor strength among different functional groups (sulfur > oxygen > carbon).
This research has potential implications for improving targeted radionuclide therapy through enhanced radiolabeling of carrier agents using astatine.