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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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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...
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Cytoskeletal filaments are polymeric forms of smaller protein subunits. However, individual cytoskeletal filaments may easily disassemble or associate with other similar filaments to form rigid structures. Microfilaments, made of actin monomers, rely on actin-binding proteins to form bundles and create networks of individual actin filaments. Microtubules rely on microtubule-associated proteins (MAPs) to form sturdy cylindrical structures. However, the proteins involved in forming complex...
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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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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...
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Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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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...
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Cycloaddition Reactions: Overview01:16

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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On-Demand Cyclophanes: Substituent-Directed Self-Assembling, Folding, and Binding.

Pierre-Thomas Skowron1, Melissa Dumartin2, Emeric Jeamet2

  • 1Institut des Sciences Moléculaires de Marseille, UMR 7313 CNRS - Université d'Aix-Marseille - École Centrale Marseille, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France.

The Journal of Organic Chemistry
|December 23, 2015
PubMed
Summary

Researchers created large quantities of unique molecular cages called dyn[4]arenes using self-assembly. By altering their functional groups, these dyn[4]arenes can be precisely designed as receptors for various ions in different environments.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Cyclophanes are macrocyclic organic compounds known for their unique structural and binding properties.
  • Self-assembly offers a powerful route for constructing complex molecular architectures.
  • Functionalization of molecular scaffolds is key to tailoring their properties.

Purpose of the Study:

  • To develop a scalable synthesis of a novel family of cyclophanes, termed dyn[4]arenes.
  • To investigate the impact of functional groups on the structural characteristics and molecular recognition capabilities of dyn[4]arenes.
  • To demonstrate the versatility of dyn[4]arenes as tailored receptors for diverse analytes.

Main Methods:

  • Gram-scale synthesis of p-cyclophanes via self-assembly of bis- or tetrafunctionalized 1,4-bisthiophenol units.
  • Disulfide bridge formation to link the building blocks.
  • Systematic variation of functional groups on the dyn[4]arene scaffold.

Main Results:

  • Successful self-assembly yielded dyn[4]arenes on a gram scale without chromatographic purification.
  • The nature and position of functional groups significantly influenced the structural assembly and binding properties.
  • Demonstrated selective binding of cations, anions, and zwitterions in both organic and aqueous media.

Conclusions:

  • Dyn[4]arenes represent a versatile class of macrocyclic receptors synthesized efficiently through self-assembly.
  • Functional group tuning provides a powerful strategy for designing bespoke receptors for specific molecular recognition tasks.
  • This approach enables the development of adaptable molecular tools for sensing and separation.