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Bis (trifluoromethyl) sulfone, CF3SO2CF3: Synthesis, vibrational and conformational properties

Abstract:

Bis (trifluoromethyl) sulfone, CF<inf>3</inf>SO<inf>2</inf>CF<inf>3</inf>, was obtained as a byproduct in the synthesis of CF<inf>3</inf>SO <inf>2</inf>SCF<inf>3</inf>. The compound was characterized by infrared and Raman spectroscopy as well quantum chemical calculations. Quantum mechanical calculations indicate the possible existence of two conformers symmetrically equivalent with C<inf>2</inf> symmetry. The preference for the staggered form was studied using the total energy scheme and the natural bond orbital (NBO) partition scheme. Additionally, the total potential energy was deconvoluted using a sixfold decomposition in terms of a Fourier-type expansion, showing that the hyperconjugative effect was dominant in stabilizing the staggered conformer. Infrared and Raman spectra of CF<inf>3</inf>SO<inf>2</inf>CF <inf>3</inf> were obtained. Harmonic vibrational wavenumbers and a scaled force field were calculated, leading to a final root mean-square deviation of 7.8 cm<sup>-1</sup> when comparing experimental and calculated wavenumbers. © 2012 Elsevier B.V. All rights reserved.