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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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DOI: 10.5155/eurjchem.2.3.289-294.416
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Citations
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Molecules 25(22), 5441, 2020
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HPLC Method for the Simultaneous Determination of the UV-Filters Butyl Methoxy Dibenzoylmethane and Octocrylene in the Presence of Their Photodegradants
Chromatographia 76(23-24), 1721, 2013
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DOI Link: https://doi.org/10.5155/eurjchem.2.3.289-294.416
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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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