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Theoretical study (CC2, DFT and PCM) of charge transfer complexes between antithyroid thioamides and TCNE: electronic CT transitions

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Abstract

A set of representative DFT and wavefunction based theoretical approaches have been used to study ionization potentials and, predominantly, electronic charge transfer transitions in the complexes formed between TCNE as an electron acceptor and both mono and bicyclic thioamides as donors. The mentioned thioamides are of pharmacological importance due to their efficient antithyroid activity. Within a few kcal mol-1 we have found six stable conformers for complexes with each of benzothioamides and four conformers for each of monocyclic thioamides. Present theoretical study satisfactorily shows that there is a good correspondence between the CC2/Def2-TZVPP calculated excitation energies for complexes in vacuum supplemented by the DFT solvent shifts and experiment. Present theoretical study contributes to deeper understanding of the electronic nature of the ground and excited states of the complexes with antithyroid activity.

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Acknowledgments

This work has been supported by the Slovak Research and Development Agency (project APVV-0 059–10) and the Project: Mobility - enhancing research, science and education at the Matej Bel University, ITMS code: 26 110 230 082, under the Operational Program Education financed by the European Social Fund. A part of the calculations was performed in the High Performance Computing Center of the Matej Bel University in Banská Bystrica using the HPCC infrastructure acquired in projects ITMS 26 230 120 002 and 26 210 120 002 (Slovak infrastructure for high-performance computing) supported by the Research & Development Operational Programme funded by the ERDF.

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Authors and Affiliations

  1. Department of Nuclear Physics and Biophysics, Faculty of Mathematics, Physics and Informatics, Comenius University, Mlynská dolina F1, SK-84248, Bratislava, Slovak Republic

    Pavel Mach

  2. Department of Chemistry, Faculty of Natural Sciences, Matej Bel University, Tajovského 40, SK-97400, Banská Bystrica, Slovak Republic

    Šimon Budzák, Miroslav Medveď & Ondrej Kyseľ

  3. Department of Chemistry, Faculty of Education, Janos Selye University, Bratislavská cesta 3322, SK-94501, Komárno, Slovak Republic

    György Juhász

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  1. Pavel Mach
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Correspondence to Šimon Budzák.

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Mach, P., Budzák, Š., Juhász, G. et al. Theoretical study (CC2, DFT and PCM) of charge transfer complexes between antithyroid thioamides and TCNE: electronic CT transitions. J Mol Model 20, 2312 (2014). https://doi.org/10.1007/s00894-014-2312-7

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