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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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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Sulfur Assimilation01:20

Sulfur Assimilation

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Sulfur is an essential element in biological systems, contributing to synthesizing key biomolecules, including amino acids such as cysteine and methionine, and cofactors such as coenzyme A and biotin. Microorganisms primarily assimilate sulfur as sulfate (SO₄²⁻) from the environment, which must undergo a series of biochemical transformations before it can be incorporated into cellular components. As sulfate is highly oxidized, it must undergo assimilatory sulfate reduction to...
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Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

579
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 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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Sulfate Separation by Selective Crystallization with a Bis-iminoguanidinium Ligand
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Sulfonium Salts as Acceptors in Electron Donor-Acceptor Complexes.

Leendert van Dalsen1, Rachel E Brown1, James A Rossi-Ashton1

  • 1Department of Chemistry, The University of Manchester, Manchester, UK.

Angewandte Chemie (International Ed. in English)
|March 23, 2023
PubMed
Summary

New sulfonium salt strategies enable sustainable generation of diverse radical species by overcoming electronic limitations in electron donor-acceptor (EDA) complexation. This approach expands accessible chemical space for radical generation.

Keywords:
Aryl RadicalArylationCharge TransferEDA ComplexSulfonium Salt

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Radical Chemistry

Background:

  • Photoactivation of electron donor-acceptor (EDA) complexes is a sustainable method for generating radical species.
  • Existing EDA complexation strategies have electronic constraints, limiting the variety of obtainable radicals.

Purpose of the Study:

  • To introduce novel EDA complexation strategies utilizing sulfonium salts.
  • To highlight the expansion of accessible chemical space for radical generation through this innovation.

Main Methods:

  • Exploiting sulfonium salts as acceptor components in EDA complexes.
  • Utilizing aryl sulfonium salts formed by arene activation.
  • Employing a "sulfonium tag" approach to relax substrate electronic constraints.

Main Results:

  • Sulfonium salts enable radical generation from native functionality.
  • The "sulfonium tag" approach significantly broadens the scope of radicals producible via EDA complexation.
  • New areas of chemical space are rendered accessible for radical generation.

Conclusions:

  • Sulfonium salt-based EDA complexation offers a versatile and expanded route to radical species.
  • This method overcomes previous electronic limitations, enabling broader applications in chemistry.