Synthesis, Structure and Conformational Properties of Trifluoroacetyl-trichloromethyl Disulfide, CF3C(O)SSCCl3

CANNEVA, ANTONELA; ERBEN, MAURICIO FEDERICO; BOESE, RONALD; MITZEL, NORBERT W.; DELLA VÉDOVA, CARLOS OMAR

Moscow

Simposio; 14 European Symposium on Gas Phase Electron Diffraction; 2011

In the present study, we have prepared the trifluoroacetyl trichloromethyl disulfide molecule, CF3C(O)SSCCl3, a novel compound that is suitable for ex­ten­ding the structural, conformational and vibrational information available for simple disulfide compounds. Pure CF3C(O)SSCCl3, has been prepared by reac­tion between CF3C(O)SH and ClSCCl3  in quantitative yield. The confor­mational properties of the novel molecule have been studied by vibrational spectroscopy, by measuring the gaseous infrared spectrum and the FT-Raman of the liquid. The most stable form presents C1 symmetry and a synperiplanar  (syn) orient­a­tion of the carbonyl group with respect to the disulfide bond. In addition, a preliminary analysis of the structure of a single crystal, grown in situ by using X-ray diffraction analysis at low temperature is presented. The crystalline solid seems to consist of molecules with syn conformation and the usual gauche orientation around the disulfide bond. Quantum chemical calculations at HF, B3LYP and MP2 levels of approximations with extended basis sets [up to 6-311+G(3df)], have been applied to complement the experimental results.