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Bis(pentafluoroethyl)phosphinous acid, (C(2)F(5))(2)POH, is synthesized and found to be more stable than its phosphane oxide tautomer. This phosphinous acid is stable in gas and solution but shows temperature-dependent tautomerism in neat liquid form.

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Area of Science:

  • Organophosphorus chemistry
  • Fluorine chemistry
  • Computational chemistry

Background:

  • Phosphinous acids are a class of organophosphorus compounds.
  • Tautomerism between phosphinous acid and phosphane oxide forms is known.
  • Previous studies have focused on trifluoromethyl derivatives.

Purpose of the Study:

  • To synthesize and characterize bis(pentafluoroethyl)phosphinous acid, (C(2)F(5))(2)POH.
  • To investigate the tautomeric equilibrium between the phosphinous acid and phosphane oxide forms.
  • To compare the stability of the two tautomers using theoretical calculations.

Main Methods:

  • Multi-step synthesis starting from (C(2)F(5))(3)PF(2).
  • Reaction with tributyltin hydride (Bu(3)SnH) followed by treatment with hydrogen bromide (HBr).
  • Density functional theory (DFT) calculations at the B3PW91/6-311G(3d,p) level.
  • Vibrational and multinuclear NMR spectroscopy.
  • Quantum-chemical calculations.

Main Results:

  • Bis(pentafluoroethyl)phosphinous acid, (C(2)F(5))(2)POH, was successfully synthesized in 70% yield.
  • DFT calculations predict the phosphinous acid tautomer to be more stable than the phosphane oxide tautomer by 11.7 kJ mol(-1).
  • The phosphinous acid isomer is the only detectable form in the gas phase and in solution.
  • A temperature-dependent tautomeric equilibrium between the phosphinous acid and phosphane oxide isomers was observed in the neat liquid.

Conclusions:

  • Bis(pentafluoroethyl)phosphinous acid is the second known phosphinous acid more stable than its phosphane oxide tautomer.
  • The compound exists predominantly as the phosphinous acid tautomer under typical conditions.
  • The study highlights the importance of experimental and computational methods in understanding tautomeric equilibria in organophosphorus compounds.