European Journal of Chemistry 2011, 2(3), 289-294. doi:10.5155/eurjchem.2.3.289-294.416

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, Accepted: 08 Apr 2011, Published: 30 Sep 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.

2_3_289-294_800


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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[1]. Jan Zawadiak, Marek Mrzyczek
Correlation of substituted aromaticβ-diketones' characteristic protons chemical shifts with Hammett substituent constants
Magnetic Resonance in Chemistry  , n/a, 2013
DOI: 10.1002/mrc.4001
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[2]. Jutta Kockler, Cherie A. Motti, Sherryl Robertson, Michael Oelgemöller, Beverley D. Glass
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
DOI: 10.1007/s10337-013-2541-4
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[3]. Arti Sharma, Asha Jain, Sanjiv Saxena
The structure-activity relationship of some hexacoordinated dimethyltin(IV) complexes of fluorinated β-diketone/β-diketones and sterically congested heterocyclic β-diketones
Applied Organometallic Chemistry  29(8), 499, 2015
DOI: 10.1002/aoc.3321
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[4]. E. A. Shokova, J. K. Kim, V. V. Kovalev
1,3-Diketones. Synthesis and properties
Russian Journal of Organic Chemistry  51(6), 755, 2015
DOI: 10.1134/S1070428015060019
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[5]. Jan Zawadiak, Marek Mrzyczek
Super-strong bathochromic and hyperchromic effects of methoxy-substituted aromatic bis(1,3-diketones)
Mendeleev Communications  24(1), 45, 2014
DOI: 10.1016/j.mencom.2013.12.015
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[6]. A. A. Turmasova, V. V. Konshin, Dzh. N. Konshina
Synthesis of (1,3-adamantylene)bis-1,3-dicarbonyl compounds
Russian Journal of General Chemistry  84(7), 1273, 2014
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[7]. Karuna Maheshwari, Manish Kumar Srivastava, Sanjiv Saxena, Asha Jain
Investigation of pharmacophore and antipharmacophore features of certain dimethyltin(IV) complexes of flexible N-protected amino acids and fluorinated β-diketone/β-diketones
Applied Organometallic Chemistry  31(2), e3570, 2017
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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. 21 Oct. 2019
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)

DOI Link: https://doi.org/10.5155/eurjchem.2.3.289-294.416

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