KETO–ENOL TAUTOMERISM IN β-DICARBONYLS STUDIED BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY: II. SOLVENT EFFECTS ON PROTON CHEMICAL SHIFTS AND ON EQUILIBRIUM CONSTANTS

Author:

Rogers Max T.,Burdett Jane L.

Abstract

The effect of various solvents on the proton chemical shifts of a number of acyclic β-di-ketones and β-ketoesters has been observed by nuclear magnetic resonance spectroscopy. These shifts are discussed in terms of the dissociation of intramolecular and intermolecular hydrogen bonds on dilution. A complex of benzene with the enol tautomer of the β-dicarbonyl molecule is proposed. The effect of solvents on the position of the tautomeric equilibrium is discussed.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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