Journal of Organic Chemistry p. 3295 - 3299 (1980)
Update date:2022-08-11
Topics:
Olmstead, William N.
Margolin, Zafra
Bordwell, Frederick G.
A method is described for determining equilibrium constants between the indicators triphenylmethane and diphenylmethane (DH) and the solvent Me2SO; pKa values of 32.1 and 35.1 are assigned to DH and Me2SO, respectively.This method is then extended to the determination of pKa values for MeOH, EtOH, i-PrOH, and H2O in Me2SO, taking into account the leveling effects of the solvent, homohydrogen bonding ("homoconjugation"), and ion pairing.The pKa values of simple alcohols in Me2SO were found to increase progressively with molecular size: MeOH (29.0) < EtOH (29.8) < i-PrOH (30.2).The pKa of H2O in Me2SO is higher (31.4), but is lower than that of t-BuOH (32.2).
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