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Related Concept Videos

Racemic Mixtures and the Resolution of Enantiomers02:30

Racemic Mixtures and the Resolution of Enantiomers

A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit different...
Prochirality02:05

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 Alkenes02:46

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.
Formation of Halohydrin from Alkenes02:41

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.
Radical Halogenation: Stereochemistry01:33

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:
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

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Halogen Bonding versus Hydrogen Bonding in Driving Self-Assembly Processes Perfluorocarbon-hydrocarbon self-assembly, part IX. This work was supported by MURST (Cofinanziamento '99) and EU (COST-D12-0012). We thank Dr. A. Lunghi and Dr. P. Cardillo (Stazione Sperimentale Combustibili, S. Donato Milanese, Italy) for ARC experiments. Part VIII: ref. 9.

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Related Experiment Video

Updated: Jul 18, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Resolution of Racemic 1,2-Dibromohexafluoropropane through Halogen-Bonded Supramolecular Helices.

Farina1, Meille, Messina

  • 1Dipartimento di Chimica, Politecnico di Milano, 7, via Mancinelli, I-20131 Milano (Italy).

Angewandte Chemie (International Ed. in English)
|August 24, 1999
PubMed
Summary

This study reveals halogen bonds in cocrystals, forming enantiopure helical structures. This supramolecular self-assembly enables the separation of racemic compounds.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Crystallography

Background:

  • Halogen bonding is a significant intermolecular force.
  • Perfluoroalkyl bromides and bromide ions are key components in crystal engineering.
  • Supramolecular self-assembly offers pathways for chiral resolution.

Purpose of the Study:

  • To investigate the role of halogen bonds in cocrystal formation.
  • To explore the self-assembly of perfluorocarbon-hydrocarbon systems.
  • To achieve chiral resolution of racemic compounds using supramolecular methods.

Main Methods:

  • Cocrystallization of (-)-sparteinium hydrobromide and (S)-1,2-dibromohexafluoropropane.
  • X-ray crystallography to determine crystal structure.
  • Analysis of intermolecular interactions, specifically halogen bonds.

Main Results:

  • Cocrystals of (-)-sparteinium hydrobromide and (S)-1,2-dibromohexafluoropropane exhibit halogen bonding.
  • The identified halogen bonds lead to the formation of infinite, enantiopure supramolecular helices.
  • The perfluorocarbon-hydrocarbon self-assembly successfully resolved racemic 1,2-dibromohexafluoropropane.

Conclusions:

  • Halogen bonding is a powerful tool for constructing ordered supramolecular architectures.
  • Enantiopure helical structures can be reliably formed through directed self-assembly.
  • This approach provides an effective method for the chiral resolution of specific organic compounds.