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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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To draw Lewis structures for complicated molecules and molecular ions, it is helpful to follow a step-by-step procedure as outlined:
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The ionization of a molecule into a molecular ion inside the mass spectrometer causes instability in the molecule's structure due to the loss of an electron. This eventually leads to the fragmentation or breaking of some bonds in the molecule. The fragmentation occurs predominantly at specific bonds to yield relatively stable fragments.
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Resonance

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The Lewis structure of a nitrite anion (NO2−) may actually be drawn in two different ways, distinguished by the locations of the N-O and N=O bonds.
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Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...
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Synthesis and Characterization of Functionalized Metal-organic Frameworks
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NO2 bond cleavage by MoL3 complexes.

Miranda F Shaw1, Narges Mahdizadeh Ghohe, Alireza Ariafard

  • 1School of Chemistry, University of Tasmania, Private Bag 75, Hobart, TAS 7001, Australia. Brian.Yates@utas.edu.au.

Dalton Transactions (Cambridge, England : 2003)
|November 13, 2013
PubMed
Summary
This summary is machine-generated.

Molybdenum complexes cleave nitrogen dioxide (NO2) via direct bond breaking, forming molybdenum oxide and nitrosyl complexes. This reaction likely proceeds through a triplet η(1)-O isomer at ambient conditions.

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Area of Science:

  • Organometallic Chemistry
  • Computational Chemistry
  • Inorganic Chemistry

Background:

  • Molybdenum complexes (MoL3) react with small molecules.
  • The reaction of Mo(NRAr)3 with nitrogen dioxide (NO2) forms molybdenum oxide and nitrosyl complexes.
  • The mechanism of this N-O bond cleavage requires investigation.

Purpose of the Study:

  • To investigate the mechanism and electronic rearrangement of NO2 cleavage by Mo(NRAr)3.
  • To compare theoretical calculations with experimental findings.
  • To determine the most likely reaction pathway.

Main Methods:

  • Density Functional Theory (DFT) calculations.
  • Modeling using a simplified Mo(NH2)3 system.
  • Modeling using the full experimental ligand [N((t)Bu)(3,5-dimethylphenyl)].

Main Results:

  • Calculations identified multiple coordination modes, isomerization, and bond-breaking pathways.
  • The lowest calculated barrier for direct N-O bond cleavage was 7 kJ mol(-1) for the singlet η(2)-N,O model complex.
  • For the full ligand, the lowest barrier was 21 kJ mol(-1) via the triplet η(1)-O isomer, with a strong thermodynamic driving force to products.
  • Direct N-O bond cleavage via an η(1)-O complex is the likely mechanism.

Conclusions:

  • The reaction proceeds via direct N-O bond cleavage of NO2 by molybdenum complexes.
  • The triplet η(1)-O isomer pathway is favored under ambient conditions.
  • The second equivalent of the metal ligand binds irreversibly to the released nitric oxide, rather than being essential for cleavage.