Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Synthesis, Structural Characterization and Electrochemical Properties of Copper(II) Complexes with Functionalized Thiosemicarbazones Derived from 5-Acetylbarbituric Acid

Alfonso Castiñeiras
ORCID logo ,
Nuria Fernández-Hermida
,
Isabel García-Santos
* ORCID logo ,
Lourdes Gómez-Rodríguez
,
Antonio Frontera
ORCID logo ,
Juan Niclós-Gutiérrez
ORCID logo
Version 1 : Received: 19 April 2024 / Approved: 22 April 2024 / Online: 22 April 2024 (12:56:06 CEST)

How to cite: Castiñeiras, A.; Fernández-Hermida, N.; García-Santos, I.; Gómez-Rodríguez, L.; Frontera, A.; Niclós-Gutiérrez, J. Synthesis, Structural Characterization and Electrochemical Properties of Copper(II) Complexes with Functionalized Thiosemicarbazones Derived from 5-Acetylbarbituric Acid. Preprints 2024, 2024041405. https://doi.org/10.20944/preprints202404.1405.v1 Castiñeiras, A.; Fernández-Hermida, N.; García-Santos, I.; Gómez-Rodríguez, L.; Frontera, A.; Niclós-Gutiérrez, J. Synthesis, Structural Characterization and Electrochemical Properties of Copper(II) Complexes with Functionalized Thiosemicarbazones Derived from 5-Acetylbarbituric Acid. Preprints 2024, 2024041405. https://doi.org/10.20944/preprints202404.1405.v1

Abstract

The reaction between 5-acetylbarbituric acid and 4-dimethylthiosemicarbazide or 4-hexamethyleneiminyl thiosemicarbazide produces 5-acetylbarbituric-4-dimethylthiosemicarbazone (H2AcbDM) and 5-acetylbarbituric-4N-hexamethyleneiminyl thiosemicarbazone (H2Acbhexim). Eight new complexes with different cooper (II) salts have been prepared and characterized using elemental analysis, molar conductance, UV–vis, ESI-HRMS, FT-IR, magnetic moment, EPR and cyclic voltammetry. In addition, three-dimensional molecular structures of [Cu(HAcbDM)(H2O)2](NO3)·H2O (3a), [Cu(HAcbDM)(H2O)2]ClO4 (4), and [Cu(HAcbHexim)Cl] (6) were determined by single crystal X-ray crystallography, and was carried out an analysis of their supramolecular structure. The H-bonded assemblies were further studied energetically using DFT calculations, MEP surface and QTAIM analyses. In these complexes, the thiosemicarbazone coordinates to the metal ion in an ONS-tridentate manner, in the O-enolate/S-thione form. The electrochemical behavior of the thiosemicarbazones and their copper(II) complexes has been investigated at room temperature using the cyclic voltammetry technique in DMFA. The Cu(II)/Cu(I) redox system was found to be consistent with the quasi-reversible diffusion-controlled process.

Keywords

thiosemicarbazone complexes, 5-acetylbarbituric derivatives, crystal structures, cooper(II) complexes, electrochemical analysis

Subject

Chemistry and Materials Science, Inorganic and Nuclear Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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