Acylated cyanoimido-complexes trans-[Mo(NCN){NCNC(O)R}(dppe)(2)]Cl and their reactions with electrophiles: chemical, electrochemical and theoretical study

Dalton Trans. 2012 Dec 7;41(45):13876-90. doi: 10.1039/c2dt30867c. Epub 2012 Jun 14.

Abstract

Treatment of a dichloromethane solution of trans-[Mo(NCN){NCNC(O)R}(dppe)(2)]Cl [R = Me (1a), Et (1b)] (dppe = Ph(2)PCH(2)CH(2)PPh(2)) with HBF(4), [Et(3)O][BF(4)] or EtC(O)Cl gives trans-[Mo(NCN)Cl(dppe)(2)]X [X = BF(4) (2a) or Cl (2b)] and the corresponding acylcyanamides NCN(R')C(O)Et (R' = H, Et or C(O)Et). X-ray diffraction analysis of 2a (X = BF(4)) reveals a multiple-bond coordination of the cyanoimide ligand. Compounds 1 convert to the bis(cyanoimide) trans-[Mo(NCN)(2)(dppe)(2)] complex upon reaction with an excess of NaOMe (with formation of the respective ester). In an aprotic medium and at a Pt electrode, compounds 1 (R = Me, Et or Ph) undergo a cathodically induced isomerization. Full quantitative kinetic analysis of the voltammetric behaviour is presented and allows the determination of the first-order rate constants and the equilibrium constant of the trans to cis isomerization reaction. The mechanisms of electrophilic addition (protonation) to complexes 1 and the precursor trans-[Mo(NCN)(2)(dppe)(2)], as well as the electronic structures, nature of the coordination bonds and electrochemical behaviour of these species are investigated in detail by theoretical methods which indicate that the most probable sites of the proton attack are the oxygen atom of the acyl group and the terminal nitrogen atom, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Electrochemical Techniques*
  • Imides / chemistry*
  • Molecular Conformation
  • Molybdenum / chemistry*
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Quantum Theory*
  • Stereoisomerism

Substances

  • Imides
  • Organometallic Compounds
  • Molybdenum