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Related Concept Videos

Metal-Ligand Bonds02:51

Metal-Ligand Bonds

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The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
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Complexation Equilibria: The Chelate Effect

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In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
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Formation of Complex Ions

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A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
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Acid Halides to Ketones: Gilman Reagent01:14

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Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.3K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Complexation Equilibria: Factors Influencing Stability of Complexes01:09

Complexation Equilibria: Factors Influencing Stability of Complexes

515
In complexation reactions, metal cations are the electron pair acceptors, and the ligands are the electron pair donors. The stability of the metal complexes depends primarily on the complexing ability of the central metal ion and the nature of the ligands. Generally, the complexing ability of the metal ion depends on the size and charge of the ion. As the metal ion size increases, the stability of the metal complexes decreases, provided that the valency of the metal ion and the ligands remain...
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Updated: Oct 3, 2025

Ion Mobility-Mass Spectrometry Techniques for Determining the Structure and Mechanisms of Metal Ion Recognition and Redox Activity of Metal Binding Oligopeptides
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Ion Mobility-Mass Spectrometry Techniques for Determining the Structure and Mechanisms of Metal Ion Recognition and Redox Activity of Metal Binding Oligopeptides

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Alkali metal ion binding using cyclic polyketones.

Narito Ozawa1, Kilingaru I Shivakumar2, Muthuchamy Murugavel2

  • 1Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Kita 13, Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, Japan. inokuma@eng.hokudai.ac.jp.

Chemical Communications (Cambridge, England)
|February 16, 2022
PubMed
Summary
This summary is machine-generated.

New cyclic oligoketones exhibit crown ether-like alkali metal ion binding, with applications in Finkelstein reaction catalysis. Researchers also created novel ion-binding hosts from functionalized linear polyketones.

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Crown ethers are well-known for their ability to bind alkali metal ions.
  • Cyclic oligoketones represent a class of compounds with potential for host-guest chemistry.
  • Developing new ion-binding agents is crucial for various chemical applications.

Purpose of the Study:

  • To investigate the ion-binding properties of cyclic oligoketones derived from 3,3-dimethylpentane-2,4-diones.
  • To explore the catalytic applications of these novel ion-binding hosts.
  • To synthesize new ion-binding hosts through functionalization of linear polyketones.

Main Methods:

  • Synthesis of cyclic oligoketones from 3,3-dimethylpentane-2,4-diones.
  • Spectroscopic and binding studies to determine alkali metal ion association constants in chloroform/acetonitrile.
  • Application of the synthesized compounds as catalysts in the Finkelstein reaction.
  • Terminal functionalization of linear polyketones to create new ion-binding hosts.

Main Results:

  • Cyclic oligoketones demonstrated significant alkali metal ion binding, with association constants reaching 1.7 × 10^4 M^-1.
  • The ion-binding properties were successfully utilized to catalyze the Finkelstein reaction in a low-polarity solvent.
  • Novel ion-binding hosts were successfully generated via terminal functionalization of linear polyketones.

Conclusions:

  • Cyclic oligoketones exhibit promising crown ether-like ion binding capabilities.
  • These compounds can serve as effective catalysts in reactions like the Finkelstein reaction.
  • The functionalization of polyketones offers a pathway to new, versatile ion-binding host molecules.