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Acidity of Acetophenone Enol in Aqueous Solution
Author(s) -
Haspra Pavel,
Sutter Alfred,
Wirz Jakob
Publication year - 1979
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197906171
Subject(s) - acetophenone , enol , butyrophenone , chemistry , protonation , ketone , aqueous solution , titration , propiophenone , medicinal chemistry , organic chemistry , photochemistry , inorganic chemistry , catalysis , ion , neuroscience , dopamine , haloperidol , biology
Thermodynamically unstable enols (1) are of interest as primary products of Norrish Type II cleavage of ketones—butyrophenone in this case—in alkaline solution. Since (1) quickly forms the enolate, which is only slowly protonated to the ketone (2) , it is possible to measure the p K value directly by flash photolytic “titration” (p K = 10.34 ± 0.05)