Pentafluorothiophenol

Pentafluorothiophenol is an organosulfur compound with the formula C6F5SH. It is a colorless volatile liquid. The compound is prepared by the reaction of sodium hydrosulfide and hexafluorobenzene.[1] With a pKa of 2.68, it is one of the most acidic thiols.[2] Its conjugate base has been used as a ligand in coordination chemistry[3]

Pentafluorothiophenol
Names
Other names
Pentafluorophenylthiol, 2,3,4,5,6-pentafluorobenzenethiol, 2,3,4,5,6-pentafluorothiophenol. mercapto(pentafluoro)benzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.124
UNII
Properties
C6HF5S
Molar mass 200.13
Appearance colorless liquid
Density 1.625±0.06 g/cm3
Melting point -24 °C
Boiling point 143 °C
organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References

  1. Robson, P.; Stacey, M.; Stephens, R.; Tatlow, J. C. "Aromatic polyfluoro compounds. VI. Penta- and 2,3,5,6-tetrafluorothiophenol" Journal of the Chemical Society (1960), 4754-60. doi:10.1039/jr9600004754
  2. William P. Jencks, Karin Salvesen "Equilibrium deuterium isotope effects on the ionization of thiol acids" J. Am. Chem. Soc., 1971, volume 93, pp 4433–4436. doi:10.1021/ja00747a016
  3. Torrens, Hugo "Pentafluorobenzenethiolato derivatives of the platinum group metals" Coordination Chemistry Reviews, 2000, vol. 196, pp. 331-352. doi:10.1016/S0010-8545(99)00055-7
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