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Related Concept Videos

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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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,...
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Disubstituted Cyclohexanes: cis-trans Isomerism02:37

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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.
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Stability of Substituted Cyclohexanes02:30

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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.
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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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Cycloalkanes02:28

Cycloalkanes

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Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
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Characteristics and Nomenclature of Copolymers01:24

Characteristics and Nomenclature of Copolymers

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Copolymers are the products obtained from the polymerization of multiple monomer species. So, in a polymer chain itself, there can be multiple repeating units that come from different monomers. The process of synthesizing a polymer from different monomer species is called copolymerization. When two monomers are involved, the polymer is known as a bipolymer. Polymers with three and four monomers are termed terpolymers and quaterpolymers, respectively. Figure 1 depicts the copolymerization of...
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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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On the multivalency of large-ring cyclodextrins.

Alexander Kantardjiev1, Petko Ivanov1

  • 1Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, ul. Acad. G. Bonchev, bloc 9, 1113, Sofia, Bulgaria.

Carbohydrate Research
|July 7, 2023
PubMed
Summary

Large-ring cyclodextrins (LR-CDs) show high affinity for adamantane molecules. These cyclodextrins, with multiple binding sites, are promising for multivalent ligand applications.

Keywords:
AMBERCluster analysisGlycam06Inclusion complexesLarge-ring cyclodextrinsMD

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Area of Science:

  • Supramolecular Chemistry
  • Computational Chemistry

Background:

  • Cyclodextrins (CDs) are cyclic oligosaccharides with hydrophobic cavities.
  • Large-ring cyclodextrins (LR-CDs) offer expanded cavity sizes for accommodating larger guests.
  • Understanding host-guest interactions is crucial for designing novel molecular receptors.

Purpose of the Study:

  • To investigate the binding affinity and stoichiometry of large-ring cyclodextrins with adamantane guests.
  • To explore the potential of LR-CDs as multivalent receptors using molecular dynamics simulations.

Main Methods:

  • Molecular dynamics simulations were employed to study inclusion complex formation.
  • Analysis of simulation trajectories to determine guest occupancy and binding patterns.
  • Cluster analysis using k-mean and hierarchical methods to identify binding site characteristics.

Main Results:

  • LR-CDs exhibit high affinity for adamantane molecules, a hydrophobic guest.
  • CD11, CD12, CD13, and CD14 showed varying degrees of adamantane inclusion, with 2-4 guests observed.
  • CD21 and CD26 accommodate 3-5 adamantane molecules, indicating potential for further guest binding.

Conclusions:

  • LR-CDs effectively encapsulate multiple adamantane molecules within their cavities.
  • The presence of multiple binding sites on LR-CDs makes them suitable candidates for multivalent receptor applications.
  • These findings support the development of tailored multivalent ligands for specific LR-CD hosts.