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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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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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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,...
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Naming Enantiomers02:21

Naming Enantiomers

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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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Chirality02:25

Chirality

32.0K
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.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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A bifunctional chiral [2]catenane based on 1,1'-binaphthyl-phosphates.

R Mitra1, M Thiele, F Octa-Smolin

  • 1Institute of Organic Chemistry, Department of Chemistry, University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany. jochen.niemeyer@uni-due.de.

Chemical Communications (Cambridge, England)
|April 9, 2016
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel catenane using a calcium bisphosphate template and ring-closing metathesis. This bifunctional molecule, featuring chiral binaphthyl-phosphates, shows potential as an artificial receptor for dicationic guests.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Mechanically Interlocked Molecules (MIMs) offer unique structural and functional properties.
  • Chiral bisphosphates are valuable building blocks in asymmetric synthesis and host-guest chemistry.
  • Template-directed synthesis is a powerful strategy for constructing complex molecular architectures.

Purpose of the Study:

  • To synthesize a novel [2]catenane incorporating chiral 1,1'-binaphthyl-phosphate units.
  • To investigate the potential of this new catenane structure as a host molecule.
  • To explore the application of mechanically interlocked bisphosphates as artificial receptors.

Main Methods:

  • Synthesis of the [2]catenane via ring-closing metathesis.
  • Utilisation of a calcium bisphosphate template for directed assembly.
  • Characterization of the synthesized catenane structure.

Main Results:

  • Successful synthesis of a novel [2]catenane structure.
  • The catenane possesses two chiral 1,1'-binaphthyl-phosphate moieties, creating a bifunctional system.
  • Preliminary binding studies indicate potential for recognizing dicationic guest molecules.

Conclusions:

  • The developed synthetic route provides access to novel chiral catenanes.
  • The bifunctional nature of the catenane is confirmed.
  • Mechanically interlocked bisphosphates represent a promising class of artificial receptors for specific guest molecules.