Synthesis, spectroscopic characterization, and DFT analysis of dichlorido(η6-p-cymene)ruthenium(II) complexes with isonicotinate-polyethylene glycol ester ligands
Ruthenium complexes have gained significant attention due to the ruthenium similarity to iron, lower toxicity, and higher anticancer effectiveness than other compounds. In this contribution, five new isonicotinate-polyethylene glycol ester ligands were synthesised and characterised by NMR and IR spe...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2023-01-01
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| Series: | Journal of the Serbian Chemical Society |
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| Online Access: | https://doiserbia.nb.rs/img/doi/0352-5139/2023/0352-51392300070E.pdf |
| _version_ | 1827288424882634752 |
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| author | Eichhorn Thomas Dimić Dušan Marković Zoran Kaluđerović Goran N. |
| author_facet | Eichhorn Thomas Dimić Dušan Marković Zoran Kaluđerović Goran N. |
| author_sort | Eichhorn Thomas |
| collection | DOAJ |
| description | Ruthenium complexes have gained significant attention due to the ruthenium similarity to iron, lower toxicity, and higher anticancer effectiveness than other compounds. In this contribution, five new isonicotinate-polyethylene glycol ester ligands were synthesised and characterised by NMR and IR spectroscopies. The corresponding Ru(II) complexes were also obtained, and their structure was investigated by traditional methods. The optimisation of structures was performed at B3LYP/6-31+G(d,p) level of theory for H, C, N and O atoms and B3LYP/LanL2DZ for Ru. The intramolecular stabilisation interactions were assessed through the natural bond orbital approach. The NMR chemical shifts were predicted by the gauge independent atomic orbital method and compared to the experimental values. High correlation coefficients and low mean absolute errors between these data sets proved that the predicted structures described well the experimental ones. The theoretical and experimental IR spectra were also compared, and differences in the most notable bands were described. One of the ligands (L5) and complexes (5) showed fluorescent properties due to methylisatoic moiety. The electronic spectra of this compound were modelled by the time dependent-density functional theory method. The difference of 11 nm between the experimental and the theoretical wavelength was explained by the interactions between the solvent and the solute. Further biological and theoretical studies are advised for this series of compounds. |
| first_indexed | 2024-04-24T11:31:28Z |
| format | Article |
| id | doaj.art-e3e6ea9e313a44449df8636b49d5cbe3 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-04-24T11:31:28Z |
| publishDate | 2023-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-e3e6ea9e313a44449df8636b49d5cbe32024-04-10T10:17:11ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212023-01-0188121335135410.2298/JSC230412070E0352-51392300070ESynthesis, spectroscopic characterization, and DFT analysis of dichlorido(η6-p-cymene)ruthenium(II) complexes with isonicotinate-polyethylene glycol ester ligandsEichhorn Thomas0https://orcid.org/0000-0002-6302-1357Dimić Dušan1https://orcid.org/0000-0001-8127-5396Marković Zoran2https://orcid.org/0000-0001-5964-049XKaluđerović Goran N.3https://orcid.org/0000-0001-5168-1000Department of Engineering and Natural Sciences, University of Applied Sciences Merseburg, Merseburg, GermanyUniversity of Belgrade, Faculty of Physical Chemistry, Belgrade, SerbiaInstitute of Information Technologies, University of Kragujevac, Kragujevac, SerbiaDepartment of Engineering and Natural Sciences, University of Applied Sciences Merseburg, Merseburg, GermanyRuthenium complexes have gained significant attention due to the ruthenium similarity to iron, lower toxicity, and higher anticancer effectiveness than other compounds. In this contribution, five new isonicotinate-polyethylene glycol ester ligands were synthesised and characterised by NMR and IR spectroscopies. The corresponding Ru(II) complexes were also obtained, and their structure was investigated by traditional methods. The optimisation of structures was performed at B3LYP/6-31+G(d,p) level of theory for H, C, N and O atoms and B3LYP/LanL2DZ for Ru. The intramolecular stabilisation interactions were assessed through the natural bond orbital approach. The NMR chemical shifts were predicted by the gauge independent atomic orbital method and compared to the experimental values. High correlation coefficients and low mean absolute errors between these data sets proved that the predicted structures described well the experimental ones. The theoretical and experimental IR spectra were also compared, and differences in the most notable bands were described. One of the ligands (L5) and complexes (5) showed fluorescent properties due to methylisatoic moiety. The electronic spectra of this compound were modelled by the time dependent-density functional theory method. The difference of 11 nm between the experimental and the theoretical wavelength was explained by the interactions between the solvent and the solute. Further biological and theoretical studies are advised for this series of compounds.https://doiserbia.nb.rs/img/doi/0352-5139/2023/0352-51392300070E.pdfruthenium(ii) complexesdftnboisonicotinateirnmr |
| spellingShingle | Eichhorn Thomas Dimić Dušan Marković Zoran Kaluđerović Goran N. Synthesis, spectroscopic characterization, and DFT analysis of dichlorido(η6-p-cymene)ruthenium(II) complexes with isonicotinate-polyethylene glycol ester ligands Journal of the Serbian Chemical Society ruthenium(ii) complexes dft nbo isonicotinate ir nmr |
| title | Synthesis, spectroscopic characterization, and DFT analysis of dichlorido(η6-p-cymene)ruthenium(II) complexes with isonicotinate-polyethylene glycol ester ligands |
| title_full | Synthesis, spectroscopic characterization, and DFT analysis of dichlorido(η6-p-cymene)ruthenium(II) complexes with isonicotinate-polyethylene glycol ester ligands |
| title_fullStr | Synthesis, spectroscopic characterization, and DFT analysis of dichlorido(η6-p-cymene)ruthenium(II) complexes with isonicotinate-polyethylene glycol ester ligands |
| title_full_unstemmed | Synthesis, spectroscopic characterization, and DFT analysis of dichlorido(η6-p-cymene)ruthenium(II) complexes with isonicotinate-polyethylene glycol ester ligands |
| title_short | Synthesis, spectroscopic characterization, and DFT analysis of dichlorido(η6-p-cymene)ruthenium(II) complexes with isonicotinate-polyethylene glycol ester ligands |
| title_sort | synthesis spectroscopic characterization and dft analysis of dichlorido η6 p cymene ruthenium ii complexes with isonicotinate polyethylene glycol ester ligands |
| topic | ruthenium(ii) complexes dft nbo isonicotinate ir nmr |
| url | https://doiserbia.nb.rs/img/doi/0352-5139/2023/0352-51392300070E.pdf |
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