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Related Concept Videos

Prochirality02:05

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...
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SN2 Reaction: Stereochemistry02:23

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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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Chirality in Nature02:30

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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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Chirality02:25

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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
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Fischer Projections02:18

Fischer Projections

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Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...
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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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Related Experiment Video

Updated: Mar 16, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

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Two-Dimensional Chirality Transfer via On-Surface Reaction.

Haiming Zhang1, Zhongmiao Gong1, Kewei Sun1

  • 1Institute of Functional Nano&Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University , 199 Ren'ai Road, Suzhou, Jiangsu 215123, People's Republic of China.

Journal of the American Chemical Society
|August 23, 2016
PubMed
Summary
This summary is machine-generated.

Chirality was transferred from self-assembled molecules to new molecules using on-surface synthesis. The structure of self-assembled precursors dictated the chirality of the resulting covalently bonded products, enabling control over molecular chirality.

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Area of Science:

  • Surface chemistry
  • Organic synthesis
  • Chirality studies

Background:

  • Chirality is crucial in molecular recognition and biological processes.
  • On-surface synthesis offers a platform for creating complex molecular architectures.
  • Controlling chirality in synthesized molecules remains a significant challenge.

Purpose of the Study:

  • To achieve two-dimensional chirality transfer from self-assembled molecules to covalently bonded products.
  • To investigate the influence of precursor self-assembled structures on the chirality of synthesized molecules.
  • To explore on-surface synthesis for creating chiral oligo-p-phenylenes.

Main Methods:

  • On-surface synthesis on Au(111) substrates.
  • Utilizing 1,4-dibromo-2,5-didodecylbenzene (12DB) and 1,4-dibromo-2,5-ditridecylbenzene (13DB) as precursors.
  • Scanning tunneling microscopy (STM) for structural investigations.

Main Results:

  • Aryl-aryl coupling reaction occurred between nearest neighboring precursors, preserving the self-assembled lamellar structure.
  • Homochiral domains of precursors (12DB) yielded homochiral oligo-p-phenylenes (OPP) domains.
  • Mixed chiral geometry precursors (13DB) resulted in racemic lamellae of OPP.

Conclusions:

  • Two-dimensional chirality transfer from self-assembled precursors to covalently bonded products is feasible.
  • The self-assembled structure of precursors directly dictates the chirality of the synthesized molecules.
  • On-surface synthesis provides a route to control molecular chirality through precursor design.