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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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Cyanide ion complexation by a cationic borane.

Ching-Wen Chiu1, François P Gabbaï

  • 1Department of Chemistry, Texas A&M University, College Station, Texas, 77843, USA.

Dalton Transactions (Cambridge, England : 2003)
|February 2, 2008
PubMed
Summary
This summary is machine-generated.

This study shows a cationic borane complexing cyanide ions, enabling cyanide transport in organic phases. The borane exhibits selectivity for fluoride over cyanide due to steric hindrance.

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Area of Science:

  • Organometallic Chemistry
  • Supramolecular Chemistry
  • Chemical Sensing

Background:

  • Cationic boranes are known to complex anions.
  • Previous work demonstrated complexation of fluoride ions by a specific cationic borane, [1-(Mes2B)-8-(Me3NCH2)-C10H6]+ ([2]+).

Purpose of the Study:

  • To investigate the complexation of cyanide ions by the cationic borane [2]+.
  • To characterize the resulting cyanoborate complex and determine the binding affinity and selectivity.
  • To explore the electrochemical properties of the cationic borane and its derivatives.

Main Methods:

  • Synthesis and characterization of the cyanoborate complex [1-(Mes2(NC)B)-8-(Me3NCH2)-C10H6] (2-CN).
  • Crystal structure determination of 2-CN.
  • UV-vis titration experiments to determine binding constants.
  • Electrochemical studies (cyclic voltammetry).

Main Results:

  • The cationic borane [2]+ successfully complexes cyanide ions to form the zwitterionic cyanoborate 2-CN.
  • Complexation occurs under biphasic conditions, suggesting potential for cyanide transport.
  • Binding affinity studies reveal a higher affinity for fluoride (K > 10^8 M^-1) than cyanide (K = 8.0 x 10^5 M^-1), attributed to steric effects.
  • Electrochemical studies show [2]+ is more electrophilic than its neutral precursor and undergoes irreversible reduction.

Conclusions:

  • The cationic borane [2]+ can complex cyanide, offering a potential method for cyanide transport.
  • Steric hindrance around the boron center dictates selectivity, favoring fluoride over cyanide.
  • The electrophilicity and reductive instability of [2]+ provide insights into its chemical reactivity.