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Formation of Complex Ions03:45

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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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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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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EDTA: Auxiliary Complexing Reagents01:26

EDTA: Auxiliary Complexing Reagents

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EDTA titrations are usually carried out in highly basic conditions, where the fully deprotonated form of EDTA, Y4−, actively complexes with the free metal ions in the solution. Several metal ions precipitate as hydrous oxide (hydroxides, oxides, or oxyhydroxides) under these conditions, lowering the concentration of free metal ions in the solution. For this reason, auxiliary complexing agents or ligands such as ammonia, tartrate, citrate, or triethanolamine are used in EDTA titrations to...
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Complexation Equilibria: The Chelate Effect01:19

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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Complexometric Titration: Ligands00:43

Complexometric Titration: Ligands

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Different monodentate and polydentate ligands are used as complexing agents in complexometric titration reactions. The formation of complexes by mono- and bidentate ligands involves two or more intermediate steps, limiting their use as complexing agents. In comparison, polydentate ligands can form complexes with metal ions in a single-step process, facilitating sharper end points. This means polydentate ligands, such as amino carboxylic acid derivatives, are most commonly employed in...
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Aryl-BIAN-ligated silver(I) trifluoromethoxide complex.

Shouxiong Chen1, Yangjie Huang, Xin Fang

  • 1State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, 350108, China. zweng@fzu.edu.cn.

Dalton Transactions (Cambridge, England : 2003)
|July 7, 2015
PubMed
Summary

Researchers synthesized a novel silver(I) trifluoromethoxide complex using an Aryl-BIAN ligand. This complex effectively trifluoromethoxylates organic halides, yielding benzyl trifluoromethyl ethers.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Synthetic Chemistry

Background:

  • Silver(I) complexes are versatile in catalysis and materials science.
  • Trifluoromethoxide (OCF3) functionalization is crucial for pharmaceuticals and agrochemicals.
  • Development of efficient synthetic routes for OCF3-containing compounds remains a challenge.

Purpose of the Study:

  • To synthesize and characterize a novel silver(I) trifluoromethoxide complex.
  • To investigate the electronic structure and bonding of the complex.
  • To explore the utility of the complex in trifluoromethoxylation reactions.

Main Methods:

  • Synthesis of the silver(I) complex (Aryl-BIAN)AgOCF3 via reaction of AgOCF3 with Aryl-BIAN ligand.
  • Single-crystal X-ray crystallography for structural determination.
  • Density Functional Theory (DFT) and Natural Bond Orbital (NBO) analysis for electronic structure.
  • Reactivity studies involving trifluoromethoxylation of organic halides.

Main Results:

  • Successful synthesis of the silver(I) complex (Aryl-BIAN)AgOCF3 in 75% yield.
  • X-ray crystallography revealed a distorted tetrahedral geometry around the silver center.
  • DFT and NBO analyses provided insights into electronic structure and OCF3 bonding.
  • The complex demonstrated efficient trifluoromethoxylation of benzyl bromides to benzyl trifluoromethyl ethers.

Conclusions:

  • A novel and stable silver(I) trifluoromethoxide complex has been synthesized and structurally characterized.
  • The electronic structure and bonding of the complex have been elucidated.
  • The complex serves as an effective reagent for the synthesis of benzyl trifluoromethyl ethers.