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Related Concept Videos

Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

1.6K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
1.6K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.1K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.1K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.4K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.4K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

9.8K
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...
9.8K
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

3.6K
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:
3.6K
Stereoisomers02:32

Stereoisomers

14.0K
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...
14.0K

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Stereochemistry in subcomponent self-assembly.

Ana M Castilla1, William J Ramsay, Jonathan R Nitschke

  • 1Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, United Kingdom.

Accounts of Chemical Research
|May 6, 2014
PubMed
Summary
This summary is machine-generated.

Researchers explored stereochemical information transfer in self-assembled metal-organic structures. They demonstrated control over chirality in complex architectures, advancing chiral recognition and catalysis.

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Area of Science:

  • Stereochemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Chirality is fundamental to biomolecular structure and function, with its origins in living systems remaining unclear.
  • Understanding stereochemical information transfer is crucial for replicating biological homochirality and developing advanced chiral technologies.

Purpose of the Study:

  • To investigate stereochemical information transfer in metal-organic assemblies using subcomponent self-assembly.
  • To explore the control and propagation of chirality in complex, self-assembled architectures.

Main Methods:

  • Utilized subcomponent self-assembly, forming dynamic coordinative and covalent bonds.
  • Incorporated enantiopure subcomponents into ligands for mononuclear coordination complexes.
  • Studied stereochemical communication in tetrahedral frameworks and metal-organic cages.

Main Results:

  • Demonstrated diastereomeric enrichment by communicating stereochemical information from fixed stereocenters to metal centers.
  • Achieved stereochemical coupling across significant distances (over 2 nm) in tetrahedral frameworks.
  • Synthesized enantioselective, face-capped tetrahedra and asymmetric metal-organic cages, breaking all symmetry elements.

Conclusions:

  • Subcomponent self-assembly effectively controls stereochemical information transfer in metal-organic systems.
  • This approach enables the construction of complex chiral architectures with potential applications in chiral recognition, catalysis, and molecular devices.