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Related Concept Videos

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,...
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...
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...
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...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
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.

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Structurally-variable, rigid and optically-active D2 and D3 macrocycles possessing recognition properties towards

Carmine Coluccini1, Daniele Dondi, Marco Caricato

  • 1Department of Organic Chemistry, University of Pavia, Viale Taramelli, 10-27100-Pavia, Italy.

Organic & Biomolecular Chemistry
|March 19, 2010
PubMed
Summary

Researchers synthesized rigid, homochiral macrocycles using aromatic dicarboxylic acids and BINOL-derived alcohols. These new cyclic compounds exhibit unique structural properties and form ordered nanostructures and C(60) complexes.

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Axially chiral BINOL derivatives are valuable building blocks in asymmetric synthesis.
  • Macrocyclic compounds offer unique structural and host-guest properties.
  • Controlled synthesis of rigid, homochiral macrocycles remains a challenge.

Purpose of the Study:

  • To develop a one-pot method for synthesizing rigid, homochiral macrocycles.
  • To explore the structural diversity and properties of BINOL-based macrocycles.
  • To investigate the self-assembly and host-guest capabilities of these macrocycles.

Main Methods:

  • One-pot esterification reactions utilizing aromatic dicarboxylic acids and BINOL-derived alcohols.
  • Characterization using Nuclear Magnetic Resonance (NMR) and Circular Dichroism (CD) spectroscopies.
  • X-ray crystallography for solid-state structure determination.
  • Complexation studies with C(60) fullerenes.

Main Results:

  • Successful synthesis of rigid, homochiral macrocycles with D(2) and D(3) symmetries.
  • Yields and selectivities exceeded statistical predictions.
  • NMR and CD data revealed structural variability and confirmed the embedded binaphthyl units.
  • Crystal structures showed ordered D(2) macrocycle nanostructures with tubular arrangements.
  • D(3) macrocycles formed stable complexes with C(60), with stoichiometry dependent on cavity size.

Conclusions:

  • The developed one-pot method efficiently produces rigid, homochiral macrocycles with predictable symmetries.
  • These macrocycles exhibit unique self-assembly properties in the solid state and tunable host-guest chemistry.
  • The study highlights the potential of BINOL-based macrocycles in supramolecular chemistry and materials science.