Journal of the American Chemical Society p. 1396 - 1401 (1984)
Update date:2022-08-12
Topics:
Richard
Jencks
General base catalysis of the addition of ROH is significant for 1-phenylethyl carbocations of moderate stability and is most important for weakly basic alcohols. The Bronsted slope for catalysis of the addition of trifluoroethanol to the 1-(4-methoxyphenyl)ethyl carbocation is beta equals 0. 08. The development of positive charge on the attacking alcohol decreases with decreasing stability of the carbocation. It is concluded that the observed catalysis involves hydrogen bonding and represents the transition region between fully concerted, coupled general acid-base catalysis and specific acid catalysis with solvation of the proton in the transition state.
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