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Synthesis and properties of aromatic 1,3-diketones and bis-(1,3-diketones) obtained from acetophenone and phtalic acids esters | Zawadiak | European Journal of Chemistry

Synthesis and properties of aromatic 1,3-diketones and bis-(1,3-diketones) obtained from acetophenone and phtalic acids esters

Jan Zawadiak, Marek Mrzyczek, Tomasz Piotrowski

Abstract


Dibenzoylmethane and six aromatic 1,3-diketones containing a dibenzoylmethane moiety were synthesized from acetophenone and the appropriate ester in crossed-Claisen condensations. The synthesized diketones include derivatives containing carboxyl and ester groups; bis-(1,3-diketones) were also prepared. The absorption of UV radiation of the obtained compounds was investigated in various solvents, and their molar absorption coefficients were calculated. The ratio of tautomers and keto-enol equilibrium constants were calculated using 1H NMR techniques. Aromatic bis-(1,3-diketones) demonstrated strong hyperchromic effects. The keto-enol equilibrium of the investigated compounds is strongly shifted to the enol form, especially in non-polar solvents.

2_3_289-294_800


Keyword(s)


1,3-Diketones; Tautomerism; Bis-(1,3-diketones); UV/Vis spectroscopy; Solvent effect; Sunscreens

European Journal of Chemistry, 2 (3), (2011), 289-294

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DOI: http://dx.doi.org/10.5155/eurjchem.2.3.289-294.416

 

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