page_title: Thiol
section_title: Acidity
hierarchical_section_title: Thiol / Reactions / Acidity
caption_attribution_description: English: Thiophenolat_Synthesis Deutsch: Thiophenolat-Synthese
context_page_description: A thiol or thiol derivative is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The –SH functional group itself is referred to as either a thiol group or a sulfanyl group. Thiols are the sulfur analogue of alcohols, and the word is a portmanteau of "thio-" + "alcohol", with the first word deriving from Greek θεῖον meaning "sulfur".
  Many thiols have strong odors resembling that of garlic or rotten eggs. Thiols are used as odorants to assist in the detection of natural gas, and the "smell of natural gas" is due to the smell of the thiol used as the odorant. Thiols are sometimes referred to as mercaptans. The term "mercaptan" was introduced in 1832 by William Christopher Zeise and is derived from the Latin mercurium captāns because the thiolate group bonds very strongly with mercury compounds.
context_section_description: Thiols are easily deprotonated.  Relative to the alcohols, thiols are more acidic. The conjugate base of a thiol is called a thiolate. Butanethiol has a pKₐ of 10.5 vs 15 for butanol. Thiophenol has a pKₐ of 6, versus 10 for phenol. A highly acidic thiol is pentafluorothiophenol (C₆F₅SH) with a pKₐ of 2.68. Thus, thiolates can be obtained from thiols by treatment with alkali metal hydroxides.
caption: Synthesis of thiophenolate from thiophenol
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