Original scientific paper

https://doi.org/10.5562/cca3229

Reduction Potential of Ferrocenoyl-Substituted Nucleobases. Experimental and Computational Study

Valentina Havaić ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Ante Kovačića 1, HR-10000, Zagreb, Croatia
Senka Djaković orcid.org/0000-0002-6322-1770 ; Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottijeva 6, HR-10000, Zagreb, Croatia
Jasmina Lapić orcid.org/0000-0003-3177-7536 ; Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottijeva 6, HR-10000, Zagreb, Croatia
Tin Weitner ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Ante Kovačića 1, HR-10000, Zagreb, Croatia
Davor Šakić orcid.org/0000-0002-8871-6622 ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Ante Kovačića 1, HR-10000, Zagreb, Croatia
Valerije Vrček orcid.org/0000-0003-1624-8126 ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Ante Kovačića 1, HR-10000, Zagreb, Croatia

Abstract

Organometallic derivatives of nucleobases are characterized by distinctive biological and electrochemical properties. In this work, reduction potentials of ferrocenoyl-substituted nucleobases (uracil, 5-fluorouracil, and thymine) were measured by cyclic voltammetry and calculated by using density functional methods. Both experimental (281– 296 mV) and calculated (271–293 mV) values for reduction potential E°’ show that these conjugates are much better oxidants than the parent ferrocene system. In search for the computational model, which can successfully reproduce experimental results, the M06-2X functional appeared as the optimal method in terms of efficiency and accuracy.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

redox potential; ferrocene; nucleobase; cyclic voltammetry; density functional

Hrčak ID:

198183

URI

https://hrcak.srce.hr/198183

Publication date:

29.12.2017.

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