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Related Concept Videos

Prochirality02:05

Prochirality

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...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
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,...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Published on: September 18, 2016

New chiral cyclohexylhemicucurbit[6]uril.

Riina Aav1, Elena Shmatova, Indrek Reile

  • 1Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia. riina@chemnet.ee

Organic Letters
|July 12, 2013
PubMed
Summary

Researchers synthesized the first enantiomerically pure cyclohexylhemicucurbit[6]urils (cycHC), revealing a unique ball-like structure. These novel macrocycles effectively complex with various organic molecules in solution.

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Published on: August 22, 2018

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Macrocyclic Chemistry

Background:

  • Cucurbiturils are a well-known class of macrocyclic hosts.
  • Enantiomerically pure macrocycles are crucial for chiral recognition and asymmetric synthesis.
  • Previous cucurbituril syntheses have not yielded enantiomerically pure compounds.

Purpose of the Study:

  • To synthesize the first enantiomerically pure cucurbituril derivatives.
  • To characterize the structure and conformation of the novel macrocycles.
  • To investigate the host-guest complexation properties of these new compounds.

Main Methods:

  • Synthesis of (all-S)- and (all-R)-cyclohexylhemicucurbit[6]urils (cycHC).
  • X-ray crystallography for structural determination.
  • Diffusion Nuclear Magnetic Resonance (NMR) spectroscopy to evaluate association constants.

Main Results:

  • Successful synthesis of enantiomerically pure cycHC in up to 85% yield.
  • Crystal structure confirmed a unique ball-like shape with a 'zigzag' conformation.
  • CycHC formed complexes with halides, carboxylic acids, amines, and diastereomeric complexes with methoxyphenylacetic acid in organic media.

Conclusions:

  • The development of enantiomerically pure cyclohexylhemicucurbit[6]urils represents a significant advancement in macrocyclic chemistry.
  • The unique structure and demonstrated complexation abilities suggest potential applications in chiral recognition and molecular encapsulation.
  • Further studies are warranted to explore the full scope of their utility in various chemical and biological systems.