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π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
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π Molecular Orbitals of the Allyl Radical01:27

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Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons....
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Valence Bond Theory02:42

Valence Bond Theory

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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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Complexation Equilibria: Factors Influencing Stability of Complexes01:09

Complexation Equilibria: Factors Influencing Stability of Complexes

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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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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.
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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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Gold(III) π-Allyl Complexes.

Jessica Rodriguez1, György Szalóki1, E Daiann Sosa Carrizo2

  • 1Laboratoire Hétérochimie Fondamentale et Appliquée, Université Paul Sabatier/CNRS UMR 5069, 118 Route de Narbonne, 31062, Toulouse Cedex 09, France.

Angewandte Chemie (International Ed. in English)
|November 7, 2019
PubMed
Summary
This summary is machine-generated.

Researchers report the first stable gold(III) π-allyl complexes, crucial for organometallic chemistry. These novel complexes show reactivity towards nucleophilic additions, opening new synthetic pathways.

Keywords:
allyl ligandsgold(III) complexesnucleophilic Additionstructure elucidationπ-complexes

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Area of Science:

  • Organometallic Chemistry
  • Gold Chemistry
  • Catalysis

Background:

  • Gold(III) π-complexes with alkenes, alkynes, and arenes are known.
  • Palladium(II) π-allyl complexes are vital in organometallic chemistry, notably the Tsuji-Trost reaction.
  • Gold(III) π-allyl complexes have been elusive until now.

Purpose of the Study:

  • To synthesize and characterize novel gold(III) π-allyl and π-methallyl complexes.
  • To investigate the coordination mode and stability of these complexes.
  • To explore the reactivity of gold(III) π-allyl complexes towards nucleophilic addition.

Main Methods:

  • Synthesis and isolation of (P,C)AuIII (allyl) and (methallyl) complexes.
  • Spectroscopic analyses (NMR, IR, etc.).
  • X-ray crystallography.
  • Density Functional Theory (DFT) calculations.

Main Results:

  • Successful preparation and isolation of thermally and air-stable gold(III) π-allyl and π-methallyl complexes.
  • Spectroscopic and crystallographic data confirmed a tight quasi-symmetric η3 -coordination of the allyl moiety.
  • DFT calculations supported the structural findings.
  • The π-allyl gold(III) complexes demonstrated activation towards nucleophilic additions, particularly with β-diketo enolates.

Conclusions:

  • The study reports the first stable gold(III) π-allyl complexes.
  • These complexes exhibit unique η3 -coordination and are reactive towards nucleophiles.
  • This discovery expands the scope of gold chemistry and offers potential for new synthetic methodologies.