The perfluorinated alcohols (F5C6)(F3C)(2)COH and (F5C6)(F10C5)COH: synthesis, theoretical and acidity studies, spectroscopy and structures in the solid state and the gas phase

Trapp N, Scherer H, Hayes SA, Berger R, Kuett A, Mitzel NW, Saame J, Krossing I (2011)
Physical Chemistry Chemical Physics 13(13): 6184-6191.

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Abstract / Bemerkung
The syntheses of the perfluorinated alcohols (F5C6)(F3C)(2)COH (1) and (F5C6)(C5F10)COH (2) are described. Both compounds were prepared in reasonable yields (1: 65%, 2: 85%) by reacting the corresponding ketone with C6F5MgBr, followed by acidic work-up. The alcohols were characterized by NMR, vibrational spectroscopy, single-crystal X-ray diffraction, acidity measurements and gas-phase electron diffraction. A combination of appropriate 2D NMR experiments allowed the unambiguous assignment of all signals in the F-19 spin systems, of which that of 2 was especially complex. High acidity of the alcohols is indicated by acidity measurements as well as the calculated gas phase acidities. It is also supported by the crystal structure of 2, which exhibits only a single weak intermolecular hydrogen bridge with an O center dot center dot center dot O distance of 301 pm. This shows the low donor strength of the oxygen atom in the compound, which is partly compensated through formation of two intramolecular CF center dot center dot center dot H contacts of 220 and 232 pm length to the proton not involved in the hydrogen bridge. The pK(a) values in acetonitrile are 22.2 for 1 and 22.0 for 2; their calculated gas phase acidities are 1367 and 1343 kJ mol(-1) (MP2/TZVPP level).
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Physical Chemistry Chemical Physics
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13
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13
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6184-6191
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Trapp N, Scherer H, Hayes SA, et al. The perfluorinated alcohols (F5C6)(F3C)(2)COH and (F5C6)(F10C5)COH: synthesis, theoretical and acidity studies, spectroscopy and structures in the solid state and the gas phase. Physical Chemistry Chemical Physics. 2011;13(13):6184-6191.
Trapp, N., Scherer, H., Hayes, S. A., Berger, R., Kuett, A., Mitzel, N. W., Saame, J., et al. (2011). The perfluorinated alcohols (F5C6)(F3C)(2)COH and (F5C6)(F10C5)COH: synthesis, theoretical and acidity studies, spectroscopy and structures in the solid state and the gas phase. Physical Chemistry Chemical Physics, 13(13), 6184-6191. doi:10.1039/c0cp02596h
Trapp, N., Scherer, H., Hayes, S. A., Berger, R., Kuett, A., Mitzel, N. W., Saame, J., and Krossing, I. (2011). The perfluorinated alcohols (F5C6)(F3C)(2)COH and (F5C6)(F10C5)COH: synthesis, theoretical and acidity studies, spectroscopy and structures in the solid state and the gas phase. Physical Chemistry Chemical Physics 13, 6184-6191.
Trapp, N., et al., 2011. The perfluorinated alcohols (F5C6)(F3C)(2)COH and (F5C6)(F10C5)COH: synthesis, theoretical and acidity studies, spectroscopy and structures in the solid state and the gas phase. Physical Chemistry Chemical Physics, 13(13), p 6184-6191.
N. Trapp, et al., “The perfluorinated alcohols (F5C6)(F3C)(2)COH and (F5C6)(F10C5)COH: synthesis, theoretical and acidity studies, spectroscopy and structures in the solid state and the gas phase”, Physical Chemistry Chemical Physics, vol. 13, 2011, pp. 6184-6191.
Trapp, N., Scherer, H., Hayes, S.A., Berger, R., Kuett, A., Mitzel, N.W., Saame, J., Krossing, I.: The perfluorinated alcohols (F5C6)(F3C)(2)COH and (F5C6)(F10C5)COH: synthesis, theoretical and acidity studies, spectroscopy and structures in the solid state and the gas phase. Physical Chemistry Chemical Physics. 13, 6184-6191 (2011).
Trapp, Nils, Scherer, Harald, Hayes, Stuart A., Berger, Raphael, Kuett, Agnes, Mitzel, Norbert W., Saame, Jaan, and Krossing, Ingo. “The perfluorinated alcohols (F5C6)(F3C)(2)COH and (F5C6)(F10C5)COH: synthesis, theoretical and acidity studies, spectroscopy and structures in the solid state and the gas phase”. Physical Chemistry Chemical Physics 13.13 (2011): 6184-6191.

2 Zitationen in Europe PMC

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The perfluorinated alcohols c-C6F11OH, c-C6F10-1,1-(OH)2 and c-C6F10-1-(CF3)OH.
Schaab J, Schwab M, Kratzert D, Schwabedissen J, Stammler HG, Mitzel NW, Krossing I., Chem Commun (Camb) 54(67), 2018
PMID: 30033461
Synthesis, characterization, and application of two Al(OR(F))3 Lewis superacids.
Kraft A, Trapp N, Himmel D, Böhrer H, Schlüter P, Scherer H, Krossing I., Chemistry 18(30), 2012
PMID: 22736574

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