The Tautomeric Equilibrium between Cyclopentadienyl‐1‐carboxylic Acid and Fulvene‐6,6‐diol in Aqueous Solution | Zendy

Urwyler Bernhard | Zendy; Wirz Jakob | Zendy

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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.

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