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The Tautomeric Equilibrium between Cyclopentadienyl‐1‐carboxylic Acid and Fulvene‐6,6‐diol in Aqueous Solution
Author(s) -
Urwyler Bernhard,
Wirz Jakob
Publication year - 1990
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.199007901
Subject(s) - chemistry , aqueous solution , tautomer , keto–enol tautomerism , dibasic acid , mandelic acid , carboxylic acid , hydrolysis , enol , diol , fulvene , equilibrium constant , medicinal chemistry , cyclopentadienyl complex , oxalic acid , organic chemistry , photochemistry , inorganic chemistry , catalysis
The equilibrium and kinetics of enolization of a carboxylic acid in aqueous solution have been determined for the first time. Remarkable is both the p K E value of 6.7 for 2 and the fact that fulvenediol 1 is a strong dibasic acid (p K a = 1.3, p K ′ a = 10.4) Compound 2 was obtained via 1 , formed by hydrolysis of photochemically generated fulvenone. The enol content of 2 is thus nearly nine orders of magnitude greater than that of mandelic acid.