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Stereoisomerism02:52

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Stereoisomers02:32

Stereoisomers

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 restricted...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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,...
Structural Isomerism02:34

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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A switchable palladium-complexed molecular shuttle and its metastable positional isomers.

James D Crowley1, David A Leigh, Paul J Lusby

  • 1School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, United Kingdom.

Journal of the American Chemical Society
|November 10, 2007
PubMed
Summary

Researchers designed a novel [2]rotaxane featuring a palladium-complexed macrocycle. This macrocycle can be precisely moved between different ligand sites using reversible protonation, enabling controlled molecular switches.

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Area of Science:

  • Supramolecular Chemistry
  • Coordination Chemistry
  • Materials Science

Background:

  • Development of molecular machines requires precise control over component movement.
  • Rotaxanes are promising candidates for molecular machinery due to their mechanically interlocked structures.
  • Palladium coordination complexes offer unique electronic and catalytic properties for molecular devices.

Purpose of the Study:

  • To design and synthesize a [2]rotaxane with a translocatable palladium-complexed macrocycle.
  • To investigate the control of macrocycle position using reversible protonation of ligand sites.
  • To characterize the different co-conformer states of the rotaxane system.

Main Methods:

  • Synthesis of the [2]rotaxane incorporating a palladium macrocycle and specific ligand sites (4-dimethylaminopyridine and pyridine).
  • Characterization using spectroscopic techniques (e.g., NMR) to confirm structure and purity.
  • Operational studies involving controlled protonation/deprotonation to induce and monitor macrocycle translocation.

Main Results:

  • Successful synthesis and characterization of the target [2]rotaxane.
  • Demonstration of reversible translocation of the palladium-complexed macrocycle between ligand sites via protonation.
  • Identification and isolation of four distinct co-conformer states (protonated/neutral, stable/metastable) under ambient conditions.

Conclusions:

  • The designed [2]rotaxane functions as a controllable molecular switch.
  • Reversible protonation provides a viable external stimulus for macrocycle movement.
  • The system allows for the selection and manipulation of specific co-conformer states, paving the way for advanced molecular devices.