Singh, Rajeeva published the artcileComparisons of rate constants for thiolate-disulfide interchange in water and in polar aprotic solvents using dynamic proton NMR line shape analysis, Category: alcohols-buliding-blocks, the publication is Journal of the American Chemical Society (1990), 112(3), 1190-7, database is CAplus.
The rate constants for representative thiolate-disulfide interchange reactions are larger in DMSO and DMF than in water by a factor of ∼2300 at 24°. The log of the rate constant is directly proportional to the mole fraction of D2O in mixtures of DMSO and D2O, even at small mole fractions of D2O. This linear proportionality suggests that thiolate anion is not specifically solvated by water and that hydrogen bonding is relatively unimportant in stabilizing this species. The values of ΔS⧧ for thiolate-disulfide interchange are ∼-10 cal/(deg mol), presumptively because of loss in the entropy of the reactants in going from ground to transition state, partially compensated by a gain in entropy from solvent release. Introduction of a hydroxy group β to the C-S bond slows the reaction by a factor of 2-15; the introduction of Me groups β to the C-S bond slows the rate by factors of 3-20.
Journal of the American Chemical Society published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C23H20BN, Category: alcohols-buliding-blocks.
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