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Radical Halogenation: Stereochemistry

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

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.

Prochirality

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

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.

Molecules with Multiple Chiral Centers

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

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Related Experiment Video

Updated: Jan 7, 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 functional chiral systems.

Shuguo An¹, Pengyao Xing²

¹College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, P. R. China. anshuguo@sdnu.edu.cn.

Chemical Society Reviews

|January 2, 2026

Summary

This summary is machine-generated.

The halogen bond (XB) is a powerful tool for controlling chirality in molecular and supramolecular systems. This review highlights XBs

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

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

Published on: February 15, 2016

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Last Updated: Jan 7, 2026

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

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

Published on: February 15, 2016

Area of Science:

Supramolecular Chemistry
Organic Chemistry
Materials Science

Background:

The halogen bond (XB) is a directional noncovalent interaction with significant potential in designing functional chiral systems.
XBs offer tunable interaction strength and directionality, making them valuable for constructing and controlling chirality at molecular and supramolecular levels.

Purpose of the Study:

To review the fundamental properties and applications of halogen bonds (XBs) in the construction and control of functional chiral systems.
To summarize recent advancements in XB-based crystal engineering, chiral recognition, chiroptical materials, and supramolecular assemblies.
To explore the potential of XBs in biological and biomimetic systems and provide an outlook on future research directions.

Main Methods:

Discussion of fundamental XB properties and unconventional XB types.
Summarization of recent research progress in various XB applications.
Examination of XB-mediated asymmetric catalytic systems, including mechanisms and catalyst design.
Exploration of XBs in biological and biomimetic contexts.

Main Results:

XBs are effectively employed to induce, amplify, and transfer chirality due to anisotropic electronic distribution on halogen atoms.
XB strategies enable precise construction and stereocontrol of chiral molecular assemblies, asymmetric catalysts, and chiroptical materials.
XB-mediated systems show promise in crystal engineering, chiral separation, and supramolecular assembly.

Conclusions:

Halogen bonds are versatile tools for developing advanced functional chiral systems.
Further exploration of XBs in chiral systems offers new avenues in supramolecular chemistry, asymmetric synthesis, catalysis, and materials science.
XBs hold potential for applications in biological and biomimetic systems, addressing challenges and opening future opportunities.