Spectroscopic and structural studies on phenyl and pentafluorophenyl trifluorothioacetate, and pentafluorophenyl trifluoroacetate, CF3C(O)SC6H5, CF3C(O)SC6F5 and CF3C(O)OC6F5

Cayon VM, Erben MF, Romano RM, Stammler H-G, Mitzel NW, Della Vedova CO (2023)
Physical Chemistry, Chemical Physics.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Autor*in
Cayon, Vanina M; Erben, Mauricio F; Romano, Rosana M; Stammler, Hans-GeorgUniBi; Mitzel, Norbert W.UniBi; Della Vedova, Carlos O
Abstract / Bemerkung
Phenyl and pentafluorophenyl trifluorothioacetate, CF3C(O)SC6H5 and CF3C(O)SC6F5, were prepared by condensation of CF3C(O)Cl and the corresponding mercaptan RSH under vacuum conditions. The compounds were isolated and properly characterized by using infrared spectroscopy, UV-Vis, multinuclear NMR spectroscopy techniques and by mass spectrometry. The crystal structures have been determined for both CF3C(O)SC6H5 and according to the best of our knowledge the not yet reported in the literature CF3C(O)SC6F5 species. The conformational preferences of the three title species were also determined by means of FTIR spectroscopy. In the case of CF3C(O)OC6F5, the FTIR spectrum was also measured in an Ar-matrix and a subsequent photochemical study was performed. The main stable photoproduct found, beside CO, was the ether C6F5OCF3. Quantum-chemical calculations were used to determine the conformational preferences and complement the experimental structure parameters as well as to interpret the UV-Vis spectra determined for the three species under study. As a result of all these experimental determinations complemented with computational calculations, it can be affirmed that the title compounds present a single syn conformation in the analyzed phases (syn with respect to the CO double bond and the opposite C-chalcogen single bond). This finding reconfirms the syn conformational transferability found so far for both thioesters and esters, a result that is closely related to the properties of these families in biological processes.
Erscheinungsjahr
2023
Zeitschriftentitel
Physical Chemistry, Chemical Physics
eISSN
1463-9084
Page URI
https://pub.uni-bielefeld.de/record/2969704

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Cayon VM, Erben MF, Romano RM, Stammler H-G, Mitzel NW, Della Vedova CO. Spectroscopic and structural studies on phenyl and pentafluorophenyl trifluorothioacetate, and pentafluorophenyl trifluoroacetate, CF3C(O)SC6H5, CF3C(O)SC6F5 and CF3C(O)OC6F5. Physical Chemistry, Chemical Physics. 2023.
Cayon, V. M., Erben, M. F., Romano, R. M., Stammler, H. - G., Mitzel, N. W., & Della Vedova, C. O. (2023). Spectroscopic and structural studies on phenyl and pentafluorophenyl trifluorothioacetate, and pentafluorophenyl trifluoroacetate, CF3C(O)SC6H5, CF3C(O)SC6F5 and CF3C(O)OC6F5. Physical Chemistry, Chemical Physics. https://doi.org/10.1039/d2cp05909f
Cayon, Vanina M, Erben, Mauricio F, Romano, Rosana M, Stammler, Hans-Georg, Mitzel, Norbert W., and Della Vedova, Carlos O. 2023. “Spectroscopic and structural studies on phenyl and pentafluorophenyl trifluorothioacetate, and pentafluorophenyl trifluoroacetate, CF3C(O)SC6H5, CF3C(O)SC6F5 and CF3C(O)OC6F5”. Physical Chemistry, Chemical Physics.
Cayon, V. M., Erben, M. F., Romano, R. M., Stammler, H. - G., Mitzel, N. W., and Della Vedova, C. O. (2023). Spectroscopic and structural studies on phenyl and pentafluorophenyl trifluorothioacetate, and pentafluorophenyl trifluoroacetate, CF3C(O)SC6H5, CF3C(O)SC6F5 and CF3C(O)OC6F5. Physical Chemistry, Chemical Physics.
Cayon, V.M., et al., 2023. Spectroscopic and structural studies on phenyl and pentafluorophenyl trifluorothioacetate, and pentafluorophenyl trifluoroacetate, CF3C(O)SC6H5, CF3C(O)SC6F5 and CF3C(O)OC6F5. Physical Chemistry, Chemical Physics.
V.M. Cayon, et al., “Spectroscopic and structural studies on phenyl and pentafluorophenyl trifluorothioacetate, and pentafluorophenyl trifluoroacetate, CF3C(O)SC6H5, CF3C(O)SC6F5 and CF3C(O)OC6F5”, Physical Chemistry, Chemical Physics, 2023.
Cayon, V.M., Erben, M.F., Romano, R.M., Stammler, H.-G., Mitzel, N.W., Della Vedova, C.O.: Spectroscopic and structural studies on phenyl and pentafluorophenyl trifluorothioacetate, and pentafluorophenyl trifluoroacetate, CF3C(O)SC6H5, CF3C(O)SC6F5 and CF3C(O)OC6F5. Physical Chemistry, Chemical Physics. (2023).
Cayon, Vanina M, Erben, Mauricio F, Romano, Rosana M, Stammler, Hans-Georg, Mitzel, Norbert W., and Della Vedova, Carlos O. “Spectroscopic and structural studies on phenyl and pentafluorophenyl trifluorothioacetate, and pentafluorophenyl trifluoroacetate, CF3C(O)SC6H5, CF3C(O)SC6F5 and CF3C(O)OC6F5”. Physical Chemistry, Chemical Physics (2023).

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