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Common Ion Effect03:24

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Compared with pure water, the solubility of an ionic compound is less in aqueous solutions containing a common ion (one also produced by dissolution of the ionic compound). This is an example of a phenomenon known as the common ion effect, which is a consequence of the law of mass action that may be explained using Le Châtelier’s principle. Consider the dissolution of silver iodide:
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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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Functionalized Fluorophosphonium Ions.

Marian Olaru1, Artem Schröder1, Lena Albers2

  • 1Institut für Anorganische Chemie und Kristallographie, Universität Bremen, Leobener Straße 7, 28359, Bremen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 17, 2019
PubMed
Summary

Researchers synthesized novel fluorophosphonium cations, [R2 P(F)X]+, as precursors to elusive donor-free phosphenium ions, [R2 P]+. Reductive elimination was found to be energetically unfavorable, hindering phosphenium ion generation.

Keywords:
Lewis acidsm-terphenylphosphenium ionsphosphonium ionsphosphorus

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Area of Science:

  • Organophosphorus chemistry
  • Synthetic inorganic chemistry

Background:

  • Phosphenium ions ([R2 P]+) are highly reactive intermediates.
  • Previous attempts to isolate donor-free phosphenium ions have been challenging.
  • Understanding the stability and reactivity of phosphorus cations is crucial for synthetic advancements.

Purpose of the Study:

  • To synthesize novel functionalized fluorophosphonium cations as potential precursors to donor-free phosphenium ions.
  • To investigate the feasibility of generating donor-free phosphenium ions via reductive elimination from these cations.
  • To computationally assess the thermodynamic stability of the proposed phosphenium ion formation pathway.

Main Methods:

  • Synthesis of neutral fluorophosphines (R2 PF and R2 PF3) with bulky aryl substituents (R=2,6-Mes2 C6 H3).
  • Protonation and reaction with solvated triethylsilyl ([Et3 Si]+) ions to form functionalized fluorophosphonium cations ([R2 P(F)X]+, where X=SiEt3, H, F).
  • Computational calculations (density functional theory) to determine the energy profiles for hypothetical reductive elimination reactions.

Main Results:

  • Successfully synthesized functionalized fluorophosphonium cations: [R2 P(F)SiEt3]+, [R2 P(F)H]+, and [R2 P(F)F]+.
  • Calculations revealed that the reductive elimination of [R2 P]+ from [R2 P(F)SiEt3]+ and [R2 P(F)H]+ is highly endothermic (40.1 and 190.6 kJ mol-1, respectively).
  • The synthesized fluorophosphonium cations are stable and do not readily eliminate to form the target phosphenium ions.

Conclusions:

  • The synthesized fluorophosphonium cations are stable intermediates and not effective precursors for generating donor-free phosphenium ions via reductive elimination.
  • The high endothermicity of the reductive elimination pathway indicates that direct generation of these specific phosphenium ions under these conditions is thermodynamically unfavorable.
  • This study provides valuable insights into the limitations of synthesizing elusive phosphenium ions using current synthetic strategies.