European Journal of Chemistry 2011, 2(3), 289-294 | doi: https://doi.org/10.5155/eurjchem.2.3.289-294.416 | Get rights and content

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


Jan Zawadiak (1) , Marek Mrzyczek (2,*) , Tomasz Piotrowski (3)

(1) Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, Gliwice, 44-100, Poland
(2) Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, Gliwice, 44-100, Poland
(3) Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, Gliwice, 44-100, Poland
(*) Corresponding Author

Received: 14 Mar 2011 | Revised: 07 Apr 2011 | Accepted: 08 Apr 2011 | Published: 30 Sep 2011 | Issue Date: September 2011

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.

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Editor-in-Chief
European Journal of Chemistry

Keywords


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

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DOI: 10.5155/eurjchem.2.3.289-294.416

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Citations

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How to cite


Zawadiak, J.; Mrzyczek, M.; Piotrowski, T. Eur. J. Chem. 2011, 2(3), 289-294. doi:10.5155/eurjchem.2.3.289-294.416
Zawadiak, J.; Mrzyczek, M.; Piotrowski, T. Synthesis and properties of aromatic 1,3-diketones and bis-(1,3-diketones) obtained from acetophenone and phtalic acids esters. Eur. J. Chem. 2011, 2(3), 289-294. doi:10.5155/eurjchem.2.3.289-294.416
Zawadiak, J., Mrzyczek, M., & Piotrowski, T. (2011). Synthesis and properties of aromatic 1,3-diketones and bis-(1,3-diketones) obtained from acetophenone and phtalic acids esters. European Journal of Chemistry, 2(3), 289-294. doi:10.5155/eurjchem.2.3.289-294.416
Zawadiak, Jan, Marek Mrzyczek, & Tomasz Piotrowski. "Synthesis and properties of aromatic 1,3-diketones and bis-(1,3-diketones) obtained from acetophenone and phtalic acids esters." European Journal of Chemistry [Online], 2.3 (2011): 289-294. Web. 28 Sep. 2023
Zawadiak, Jan, Mrzyczek, Marek, AND Piotrowski, Tomasz. "Synthesis and properties of aromatic 1,3-diketones and bis-(1,3-diketones) obtained from acetophenone and phtalic acids esters" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

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