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Properties of Enantiomers and Optical Activity02:24

Properties of Enantiomers and Optical Activity

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It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...
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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.
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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three...
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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...
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The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
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In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
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Insights into the Difference Between Rotaxane and Pseudorotaxane.

He-Lue Sun1, Heng-Yi Zhang1,2, Zhen Dai1

  • 1Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P.R. China.

Chemistry, an Asian Journal
|November 30, 2016
PubMed
Summary

A rotaxane featuring ferrocene and cyclodextrin was initially thought to be a true rotaxane but was actually a pseudorotaxane. Encapsulating with cucurbituril created a stable [2]rotaxane using noncovalent interactions.

Keywords:
cyclodextrinsisomerizationpseudorotaxanesrotaxanessupramolecular chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Mechanically Interlocked Molecules
  • Nanotechnology

Background:

  • Distinguishing between rotaxanes and pseudorotaxanes is crucial for understanding mechanically interlocked molecular architectures.
  • Ferrocene groups are often used as stoppers in rotaxane synthesis.
  • Cyclodextrins and cucurbiturils are common macrocyclic hosts in supramolecular chemistry.

Purpose of the Study:

  • To synthesize and characterize a novel rotaxane-like structure using ferrocene-terminated axles and cyclodextrin.
  • To investigate the stability and topological nature of the synthesized interlocked system.
  • To explore the potential of cucurbituril as stoppers in creating robust mechanically interlocked molecules.

Main Methods:

  • Synthesis of a ferrocene-based axle molecule and its complexation with alpha-cyclodextrin.
  • Photochemical studies to assess the stability of the cyclodextrin-axle complex under UV irradiation.
  • Further complexation with cucurbituril to form a heteropseudorotaxane structure.
  • Characterization of the final heteropseudorotaxane using spectroscopic and stability analyses.

Main Results:

  • The initial complex of ferrocene-axle 1 with alpha-cyclodextrin (α-CD) was identified as a pseudorotaxane, as α-CD dethreaded under UV irradiation.
  • A heteropseudorotaxane, 1⊂α-CD⋅2CB[7], was successfully synthesized by encapsulating the ferrocene groups with cucurbit[7]uril (CB[7]) units.
  • This heteropseudorotaxane exhibited high stability against thermal stress and azobenzene isomerization, behaving as a true [2]rotaxane.

Conclusions:

  • The ferrocene groups alone are insufficient to prevent dethreading of α-CD, confirming the initial structure as a pseudorotaxane.
  • Cucurbit[7]uril units can act as effective stoppers in rotaxane construction through noncovalent interactions, leading to highly stable architectures.
  • The study demonstrates a strategy for creating robust [2]rotaxanes where cyclic host molecules serve as stoppers, offering an alternative to traditional bulky covalent stoppers.