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Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is...
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The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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Introduction
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Alkenes lose one electron from the unsaturated π bond upon ionization and form stable molecular ions. Further fragmentation of alkenes occurs through three different reaction pathways. The most prominent fragmentation is the cleavage at the allylic position. The resultant allylic carbocation is resonance stabilized. In the mass spectra of terminal alkenes, this fragment appears at a mass-to-charge ratio of 41. In the internal alkenes, where there are two choices of allylic cleavage, the...
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Unsupported Mg-Alkene Bonding.

Katharina Thum1, Alexander Friedrich1, Jürgen Pahl1

  • 1Chair of Inorganic and Organometallic Chemistry, Universität Erlangen-Nürnberg, Egerlandstrasse 1, 91058, Erlangen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 16, 2020
PubMed
Summary
This summary is machine-generated.

This study reports the first isolation of intermolecular early main group metal-alkene complexes using magnesium centers. These novel magnesium-alkene complexes exhibit asymmetric bonding and are primarily electrostatic, challenging traditional coordination chemistry views.

Keywords:
Lewis acidsalkene ligandsdensity functional calculationsmagnesiumnoncovalent interactions

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Coordination Chemistry

Background:

  • Early main group metals typically form ionic compounds, not covalent coordination complexes with alkenes.
  • Traditional coordination chemistry focuses on transition metals binding to alkene ligands.
  • Understanding bonding in main group complexes is crucial for developing new catalytic systems.

Purpose of the Study:

  • To synthesize and characterize the first intermolecular early main group metal-alkene complexes.
  • To investigate the nature of the Mg-alkene bond and electron transfer.
  • To explore the coordination behavior of magnesium cations with various alkene ligands.

Main Methods:

  • Synthesis of Lewis base-free magnesium cations [(MeBDI)Mg+ and (tBuBDI)Mg+] with B(C6F5)4- counterions.
  • Structural characterization of isolated complexes using X-ray diffraction.
  • Density Functional Theory (DFT) and Atoms in Molecules (AIM) analysis to study bonding and electron distribution.

Main Results:

  • Successful isolation and structural characterization of magnesium-alkene complexes with diverse ligands.
  • Observation of asymmetric Mg-alkene bonding, featuring one short and one long Mg-C bond.
  • DFT and AIM analyses indicate minimal C=C bond change and electron transfer, suggesting electrostatic Mg2+-induced dipole interactions.

Conclusions:

  • The first intermolecular early main group metal-alkene complexes have been synthesized and characterized.
  • The Mg-alkene bond is predominantly electrostatic, differing significantly from transition metal-alkene interactions.
  • These findings expand the scope of coordination chemistry to include early main group metals with unsaturated organic molecules.