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Structure and Acidity of Organic Compounds
Author(s) -
Simon W.
Publication year - 1964
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.196406611
Subject(s) - chemistry , acidity function , solvent , yield (engineering) , cyclohexanecarboxylic acid , organic solvent , inorganic chemistry , organic chemistry , thermodynamics , aqueous solution , chemical engineering , physics , engineering
Elucidation of the structures of organic acids and bases with the aid of their acidity constants is greatly hindered by their low solubilities in water and by the small quantities of material normally available. Apparent acidity constants K * can be determined potentiometrically on small samples (about 0.5 mg) for many classes of compounds of medium acidity. The apparent acidity constants K * MCSdetermined in the solvent system methyl cellosolvel water can be correlated, in a similar manner to thermodynamic quantities, with structural parameters (e.g. Hammett's σ * and Taft's σ * values). K * MCSvalues can yield information on the axial or equatorial position of carboxyl groups in cyclohexanecarboxylic acids.