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Related Concept Videos

SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
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SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.0K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
9.0K
Stereoisomers02:32

Stereoisomers

13.1K
On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to...
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Prochirality

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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...
3.8K
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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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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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Self-assembled stereomutation with supramolecular chirality inversion.

Guofeng Liu1,2, Mark G Humphrey3, Chi Zhang1

  • 1School of Chemical Science and Engineering, Advanced Research Institute, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. China. liuguofeng@tongji.edu.cn.

Chemical Society Reviews
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Summary
This summary is machine-generated.

Supramolecular chirality inversion (SMCI) offers precise control over chiral materials. This review details SMCI principles, strategies, and applications in advanced functional materials and biological systems.

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Area of Science:

  • Supramolecular chemistry
  • Materials science
  • Chirality studies

Background:

  • Supramolecular chirality is crucial in biological processes and artificial materials.
  • Controlling supramolecular chirality, particularly inversion (SMCI), enhances understanding of chiral transfer.
  • SMCI enables the design of advanced chiral materials with tailored assembly pathways.

Purpose of the Study:

  • To comprehensively summarize the fundamental principles of supramolecular chirality inversion (SMCI).
  • To systematically review developed SMCI strategies for chiral nanostructures and assembled materials.
  • To highlight promising applications of SMCI in various scientific and technological fields.

Main Methods:

  • Review of fundamental principles governing SMCI.
  • Systematic survey of existing SMCI strategies for nanostructures and materials.
  • Analysis of applications based on SMCI-controlled chiral assemblies.

Main Results:

  • Detailed summary of SMCI principles, focusing on helical assemblies with opposite handedness.
  • Comprehensive review of diverse SMCI strategies for constructing chiral materials.
  • Identification of key applications including switches, recognition, separation, catalysis, and biomedical uses.

Conclusions:

  • SMCI is a powerful tool for controlling and understanding chiral self-assembly.
  • SMCI facilitates the development of advanced functional chiral materials.
  • Further research into SMCI holds significant potential for future scientific advancements and technological innovations.