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Substituent effects in keto-enol tautomerism. Part 3.1 influence of substitution on the equilibrium composition of of β-dicarbonyl compounds

✍ Scribed by M. Bassetti; G. Cerichelli; B. Floris

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 437 KB
Volume: 44
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(88)90039-7

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✦ Synopsis

The enol content and equilibrium free energies for the keto-enol tautomerism have been determined for a series of 1,3-diketones, at 40 OC, in deuterochloroform and dimethylsulfoxide-d (DMSO), by lH n.m.r.. Compounds containing methyl, phenyl, t-butyl, E-thienyl, trifluorome t hyl and ethoxy groups have been examined. The equilibrium free energies in DMSO are characterized by a linear additivity effect, and substituent parameters, representing the variation produced by the substituent, have been calculated. Equilibrium enthalpy and entropy have been obtained in the range of temperature 20-60 OC. A correlation between enolic

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