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Related Concept Videos

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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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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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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Deformation in a Circular Shaft01:10

Deformation in a Circular Shaft

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One of the distinctive characteristics of circular shafts is their ability to maintain their cross-sectional integrity under torsion. In other words, each cross-section continues to exist as a flat, unaltered entity, simply rotating like a solid, rigid slab. To understand the distribution of shearing stress within such a shaft, consider a cylindrical section inside this circular shaft. This section has a length of L and a radius of R, with one end fixed. The radius of the cylindrical section is...
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Thin-Walled Hollow Shafts01:15

Thin-Walled Hollow Shafts

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In analyzing a thin-walled hollow shaft subjected to torsional loading, a segment with width dx is isolated for examination. Despite its equilibrium state, this segment faces torsional shearing forces at its ends. These forces are quantitatively described by the product of the longitudinal shearing stress on the segment's minor surface and the area of this surface, leading to the concept of shear flow. This shear flow is consistent throughout the structure, indicating a uniform distribution...
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Carbon Skeletons01:12

Carbon Skeletons

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Life on Earth is carbon-based, as all macromolecules that make up living organisms contain carbon atoms. All organic compounds have a carbon backbone. Each carbon atom is tetravalent and can bond with four other atoms, making it an extraordinarily flexible component of biological molecules. Because carbon’s valence electrons are stable, it rarely becomes an ion. As the carbon chain increases in length, structural modifications such as ring structures, double bonds, and branching side...
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A molecular sheaf: doubly threaded [6]rotaxane.

Song Huang1, Zhenwen Wang1, Jinyang Wu1

  • 1College of Chemistry, Key Laboratory of Radiation Physics and Technology of Ministry of Education, Institute of Nuclear Science and Technology, Sichuan University, Chengdu, 610064, China. lhyuan@scu.edu.cn.

Chemical Communications (Cambridge, England)
|May 8, 2024
PubMed
Summary
This summary is machine-generated.

Researchers created a stable, doubly threaded [6]rotaxane using a hydrogen-bonded pyrimidine-macrocycle complex. This supramolecular assembly efficiently threads two guest molecules into a large macrocycle, achieving high yields.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Macrocyclic chemistry enables the construction of complex molecular architectures.
  • Rotaxanes, mechanically interlocked molecules, are of interest for molecular machines and materials.
  • Template-directed synthesis is crucial for controlling the assembly of interlocked structures.

Purpose of the Study:

  • To synthesize and characterize a novel doubly threaded [6]rotaxane.
  • To investigate the efficiency of a hydrogen-bonded pyrimidine-macrocycle complex as a template.
  • To assess the stability of the resulting rotaxane architecture.

Main Methods:

  • Utilized a hydrogen-bonded pyrimidine-macrocycle complex as a template.
  • Employed bispyridinium ethylenes as guest molecules for threading.
  • Confirmed the structure and yield via X-ray crystallography of the precursor.

Main Results:

  • Achieved efficient threading of two bispyridinium ethylenes into a macrocycle.
  • Synthesized a rare example of a doubly threaded [6]rotaxane in 91% yield.
  • Demonstrated the stability of the rotaxane architecture, with no observed dethreading.

Conclusions:

  • Hydrogen-bonded pyrimidine-macrocycle complexes are effective templates for rotaxane synthesis.
  • The doubly threaded [6]rotaxane exhibits remarkable stability due to its unique architecture.
  • This work provides a rare example of a large, doubly threaded rotaxane with potential applications in molecular machinery.