Density functional calculations on the conversion of azide and carbon monoxide to isocyanate and dinitrogen by a nickel to sulfur rebound mechanism

Chemistry. 2004 Apr 2;10(7):1805-14. doi: 10.1002/chem.200304840.

Abstract

Density functional calculations (B3 LYP & BP86) on a model system for the reaction between carbon monoxide and [Ni(N(3))('S(3)')](-) ('S(3)'(2-)=bis(2-mercaptophenyl)sulfide (2-)) predict a three-step mechanism. First, CO attacks the nickel to generate a pseudo "square-pyramidal" complex, in which CO, N(3) (-), and two sulfides are basal and the central S atom of the 'S(3)'(2-) ligand backs away from Ni to form a weak Ni-S apical bond. Then, CO inserts into the Ni-N bond and the weak apical Ni--S bond rebounds to its original strength as the nickel forms a square-planar intermediate. Finally, in a one-step process N(2) leaves as the remaining N atom and carbonyl rearrange to produce the nickel isocyanate product [Ni(NCO)('S(3)')](-).

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Azides / chemical synthesis
  • Azides / chemistry*
  • Carbon Monoxide / chemistry*
  • Isocyanates / chemical synthesis*
  • Isocyanates / chemistry
  • Models, Chemical
  • Molecular Conformation
  • Nickel / chemistry
  • Nitrogen / chemistry*
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Sulfur / chemistry

Substances

  • Azides
  • Isocyanates
  • Organometallic Compounds
  • Sulfur
  • Nickel
  • Carbon Monoxide
  • Nitrogen