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Valence Bond Theory02:42

Valence Bond Theory

9.1K
Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
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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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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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Halogenation of Alkenes02:46

Halogenation of Alkenes

16.4K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
16.4K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.6K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.6K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.6K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV
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Hypervalent Chalcogenonium⋅⋅⋅π Bonding Catalysis.

Qingyu Zhang1,2, Yung-Yin Chan3, Muyin Zhang1

  • 1School of Science and Engineering, The Chinese University of Hong Kong, Shenzhen, 518172, Guangdong, China.

Angewandte Chemie (International Ed. in English)
|July 6, 2022
PubMed
Summary
This summary is machine-generated.

This study introduces hypervalent chalcogenonium⋅⋅⋅π bonding catalysis using novel 1,2-oxaselenolium salts. It demonstrates metal-free alkene hydrofunctionalization and polymerization via unique seleniranium ion intermediates.

Keywords:
Chalcogen BondingHydrofunctionalizationHypervalent SeleniumLewis AcidsOrganocatalysis

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Supramolecular Chemistry

Background:

  • Hypervalent bonding involves elements beyond the standard octet.
  • Chalcogenonium ions, particularly selenium-based, are explored for novel reactivity.
  • Non-covalent interactions are increasingly utilized in catalytic design.

Purpose of the Study:

  • To establish a proof-of-concept for hypervalent chalcogenonium⋅⋅⋅π bonding catalysis.
  • To introduce a new catalytic strategy employing 1,2-oxaselenolium salts.
  • To investigate the metal-free catalytic applications of these systems.

Main Methods:

  • Synthesis of trisubstituted selenonium salts.
  • Utilizing these salts as catalysts with alkenes.
  • Characterization of reaction intermediates, including seleniranium ion-like species.
  • Analysis of the influence of counter anions on catalytic activity.

Main Results:

  • Demonstrated successful metal-free catalytic hydrofunctionalization of alkenes.
  • Achieved metal-free catalytic polymerization of alkenes.
  • Identified unconventional seleniranium ion-like intermediates.
  • Established the significant role of counter anions in modulating catalytic performance.

Conclusions:

  • Hypervalent chalcogenonium⋅⋅⋅π bonding represents a viable catalytic strategy.
  • 1,2-Oxaselenolium salts are effective catalysts for alkene transformations.
  • The choice of counter anion is critical for optimizing catalysis in these systems.