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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:

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...

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...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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...

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.

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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

Halogen Bonding Mediated Hierarchical Supramolecular Chirality.

Shuguo An¹, Aiyou Hao¹, Pengyao Xing¹

¹School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.

|August 27, 2021

Summary

Halogen bonds precisely control supramolecular chirality in self-assembled systems. This study demonstrates their use in creating novel chiral materials with tunable chiroptical properties.

Keywords:

chiroptical property coassembly halogen bond helical nanoarchitectures multicomponent

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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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Area of Science:

Supramolecular Chemistry
Materials Science
Organic Chemistry

Background:

Halogen bonds are directional forces with potential for controlling supramolecular chirality.
Their application in building functional chiral systems remains largely unexplored.

Purpose of the Study:

To investigate the manipulation of supramolecular chirality using intracomponent halogen bonds.
To establish a protocol for creating functional chiroptical materials.

Main Methods:

Formation of a C3 symmetrical supramolecular complex between cholesteryl cyanostilbene conjugates and 1,3,5-trifluoro-2,4,6-triiodobenzene.
Characterization of the resulting complex's chirality and chiroptical activity.

Main Results:

Achieved ultrahigh binding affinity (10^11 order of magnitude) via halogen bonding.
Observed inversed chirality and chiroptical activity in halogen-bonded propeller geometries compared to pristine aggregates.
Engineered nanoarchitectures including supercoiled helical structures and aligned nanotubes.

Conclusions:

Halogen bonds play a crucial role in controlling supramolecular chirality.
This work provides a method for designing functional chiroptical materials using σ-hole interactions.