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Relative to the alcohols, thiols are more acidic. The conjugate base of a thiol is called a thiolate. Butanethiol has a pK a of 10.5 vs 15 for butanol. Thiophenol has a pK a of 6, versus 10 for phenol. A highly acidic thiol is pentafluorothiophenol (C 6 F 5 SH) with a pK a of 2.68. Thus, thiolates can be obtained from thiols by treatment with ...
Likewise, any aqueous base with an association constant pK b less than about 0, corresponding to pK a greater than about 14, is leveled to OH − and is considered a strong base. [22] Nitric acid, with a pK value of around −1.7, behaves as a strong acid in aqueous solutions with a pH greater than 1. [23] At lower pH values it behaves as a ...
Nevertheless, one can generally examine acid dissociation constants to qualitatively predict or rationalize rate or reactivity trends relating to variation of the leaving group. Consistent with this picture, strong bases such as OH −, OR 2 and NR − 2 tend to make poor leaving groups, due their inability to stabilize a negative charge.
Thiophenol is an organosulfur compound with the formula C 6 H 5 SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol.The chemical structures of thiophenol and its derivatives are analogous to phenols, where the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring in phenol is replaced by a sulfur atom.
A strong base is a basic chemical compound that can remove a proton (H +) from (or deprotonate) a molecule of even a very weak acid (such as water) in an acid–base reaction. Common examples of strong bases include hydroxides of alkali metals and alkaline earth metals, like NaOH and Ca(OH) 2, respectively. Due to their low solubility, some ...
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CH 3 SH + CH 3 ONa → CH 3 SNa + CH 3 OH. The resulting thiolate anion is a strong nucleophile. It can be oxidized to dimethyl disulfide: 2CH 3 SH + [O] → CH 3 SSCH 3 + H 2 O. Further oxidation takes the disulfide to two molecules of methanesulfonic acid, which is odorless. Bleach deodorizes methanethiol in this way.
The reaction rate is proportional to the concentration of the protonated solvent molecules SH +. [6] The acid catalyst itself (AH) only contributes to the rate acceleration by shifting the chemical equilibrium between solvent S and AH in favor of the SH + species. This kind of catalysis is common for strong acids in polar solvents, such as water.