It is the cache of It is a snapshot of the page. The current page could have changed in the meantime.
Tip: To quickly find your search term on this page, press Ctrl+F or ⌘-F (Mac) and use the find bar.

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


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.



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

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

Full Text:

PDF    /    /




[1]. HPLC Method for the Simultaneous Determination of the UV-Filters Butyl Methoxy Dibenzoylmethane and Octocrylene in the Presence of Their Photodegradants
Jutta Kockler, Cherie A. Motti, Sherryl Robertson, Michael Oelgemöller, Beverley D. Glass
Chromatographia  Volume: 76  Issue: 23-24  First page: 1721  Year: 2013  

[2]. Correlation of substituted aromaticβ-diketones' characteristic protons chemical shifts with Hammett substituent constants
Jan Zawadiak, Marek Mrzyczek
Magnetic Resonance in Chemistry  First page: n/a  Year: 2013  

[3]. Super-strong bathochromic and hyperchromic effects of methoxy-substituted aromatic bis(1,3-diketones)
Jan Zawadiak, Marek Mrzyczek
Mendeleev Communications  Volume: 24  Issue: 1  First page: 45  Year: 2014  

[4]. A novel synthesis of 1,2,4-oxadiazoles and isoxazoles
Arif Kivrak, Metin Zora
Tetrahedron  Volume: 70  Issue: 4  First page: 817  Year: 2014  



[1]. Lim, H. W.; Draelos, Z. D. In Clinical Guide to Sunscreens and Photoprotection; Informa Healthcare USA, Inc., New York, 2009.

[2]. Zawadiak, J.; Mrzyczek, M. Spectrochim. Acta, Part A 2010, 75, 925-929.

[3]. Wypych, G. In PVC Degradation & Stabilization; 2nd Edition, ChemTec Publishing, Toronto, 2008.

[4]. Przybyszewska, M.; Zaborski, M.; Jakubowski, B.; Zawadiak, J. Express Polymer Lett. 2009, 3(4), 256-266.

[5]. Clegg, J. K.; Bray, D. J.; Gloe, K.; Gloe, K.; Jolliffe, K. A.; Lawrance, G. A.; Lindoy, L. F.; Meehan, G. V.; Wenzel, M. Dalton Trans. 2008, 10, 1331-1340.

[6]. Soldatov, D. V.; Zanina, A. S.; Enright, G. D.; Ratcliffe, C. I.; Ripmeester, J. A. Cryst. Growth Des. 2003, 3(6), 1005-1013.

[7]. Bao-Li, A.; Chuan-Wei, H.; Hong-Liang, M.; Qing-Yi, P.; Ming-Xin, L. J. Lumin. 2007, 127, 297-301.

[8]. Martin, D. F.; Shamma, M.; Fernelius, W. J. Am. Chem. Soc. 1958, 80(18), 4891-4895.

[9]. Xuan, W. M.; Zou, F.; Chen, L. Q.; Fang, X. M.; Lian, W.; Zhang H. Acta Phys. Chim. Sin. 2008, 24(6), 955-960.

[10]. Adam, W.; Kita, F.; Harrer, H. M.; Nau, W. M.; Zipf, R. J. Org. Chem. 1996, 61, 7056-7065.


  • There are currently no refbacks.