
Tetrahedron Letters p. 1627 - 1628 (1987)
Update date:2022-08-11
Topics:
Almstead, N.
Christ, W.
Miller, G.
Reilly-Packard, S.
Vargas, K.
Zuman, P.
Equilibria in reactions of methanol and ethanol with sulfuric acid or in hydrolyses of alkyl sulfates were followed using 13C NMR, anion-exchange HPLC, and titrations.Variations of equilibrium constant K = (ester)(H2O)/(ROH)(HSO4(1-)) with acidity indicate participation of reactions ROH2(1+) + HSO4(1-) <*> ROH(1+)SO3(1-) + H2O, accompanied by acid base equilibra involving the alcohol and ester.For mixtures containing initially 20percent (w/w) alcohol, pKMeOH2(1+) = -4.2, pKEtOH2(1+) = -3.7, pKMeOH(1+)SO3(1-) = -3.3 and pKEtOH(1+)SO3(1-) = -2.7.
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