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Acta Chimica Slovaca

The Journal of Slovak University of Technology in Bratislava

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1337-978X
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Theoretical study of a series of phenol derivatives: molecular properties vs. cytotoxicity

Martin Michalík
  • Corresponding author
  • Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia
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  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Lívia Sádecká
  • Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Vladimír Lukeš
  • Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia
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  • De Gruyter OnlineGoogle Scholar
Published Online: 2017-12-29 | DOI: https://doi.org/10.1515/acs-2017-0016

Abstract

The quantum chemical calculations using DFT were performed for 2-alkyl-4X and 2,6-dialkyl-4-X substituted phenols. Based on the optimal geometries the bond dissociation enthalpies (BDEs), proton enthalpies (PAs) and the lipophilicities were computed. Additionally, simple geometry parameter was found correlating well with experimental leukemia cell toxicity of substituted phenols. Next, we have found no linear dependence between PA or BDE values and log1/C values in gas phase or in water despite the radical toxicity mechanism proposed in the literature.

Keywords: model compounds; drug development; QSAR; substituent effect

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About the article

Published Online: 2017-12-29

Published in Print: 2017-10-26


Citation Information: Acta Chimica Slovaca, Volume 10, Issue 2, Pages 91–95, ISSN (Online) 1337-978X, DOI: https://doi.org/10.1515/acs-2017-0016.

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© Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava . This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License. BY-NC-ND 4.0

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