European Journal of Chemistry

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



Main Article Content

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


icon graph This Abstract was viewed 4213 times | icon graph Article PDF downloaded 2015 times

How to Cite
(1)
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, 289-294.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[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.
http://dx.doi.org/10.1016/j.saa.2009.12.040
PMid:20047853

[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.
http://dx.doi.org/10.3144/expresspolymlett.2009.32

[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.
http://dx.doi.org/10.1039/b716653b
PMid:18305845

[6]. Soldatov, D. V.; Zanina, A. S.; Enright, G. D.; Ratcliffe, C. I.; Ripmeester, J. A. Cryst. Growth Des. 2003, 3(6), 1005-1013.
http://dx.doi.org/10.1021/cg030016b

[7]. Bao-Li, A.; Chuan-Wei, H.; Hong-Liang, M.; Qing-Yi, P.; Ming-Xin, L. J. Lumin. 2007, 127, 297-301.
http://dx.doi.org/10.1016/j.jlumin.2007.01.008

[8]. Martin, D. F.; Shamma, M.; Fernelius, W. J. Am. Chem. Soc. 1958, 80(18), 4891-4895.
http://dx.doi.org/10.1021/ja01551a032

[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.
http://dx.doi.org/10.1021/jo960396q
PMid:11667607

Supporting Agencies

European Community
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).