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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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Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
11.9K
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...
12.7K
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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.6K
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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Prochirality02:05

Prochirality

3.8K
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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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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ProBox: A Rigid yet Dynamic Cyclophane Capable of Adaptive and Redox-Switchable Host-Guest Binding.

Zonghuan Lu1, Wanqian Lv1, Hongyi Liu1

  • 1School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China.

Organic Letters
|May 8, 2023
PubMed
Summary
This summary is machine-generated.

Researchers designed a novel pyrrolodithiin-derived box-like cyclophane (ProBox) with an adaptive, stimuli-responsive cavity. This ProBox molecule can bind guests and release them using electrochemical oxidation, paving the way for molecular machines.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Cyclophanes are macrocyclic organic compounds known for their host-guest chemistry.
  • Stimuli-responsive materials offer dynamic properties for advanced applications.
  • Adaptive molecular architectures are key for developing molecular machines.

Purpose of the Study:

  • To design and synthesize a novel box-like cyclophane with adaptive geometry.
  • To investigate the stimuli-responsive and host-guest properties of the designed cyclophane.
  • To explore the potential applications of this cyclophane in molecular switches and machines.

Main Methods:

  • Design and synthesis of a pyrrolodithiin-derived cyclophane (ProBox).
  • Structural characterization of the ProBox cyclophane and its complexes.
  • Investigation of the cavity's adaptability to guests of varying sizes and shapes.
  • Electrochemical studies to demonstrate redox-switchable guest release.

Main Results:

  • Successful construction of the ProBox cyclophane with a dynamic, foldable dithiin subunit.
  • Demonstration of the cyclophane's compressible cavity, transforming from hex-nut to rectangular geometry.
  • Formation of pseudorotaxane complexes with guests of diverse sizes and shapes.
  • Evidence of successful dethreading of guest molecules via electrochemical oxidation.

Conclusions:

  • The ProBox cyclophane exhibits adaptive geometry and stimuli-responsive host-guest binding.
  • The redox-switchable nature of ProBox enables controlled guest complexation and release.
  • This work presents a promising platform for the development of advanced molecular switches and machines.