Synthesis, characterization, DFT quantum chemical calculations and catalytic properties of azobenzene-bearing Schiff base palladium(II) complexes for the Suzuki-Miyaura Cross-Coupling reaction in aqueous solvent

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dc.contributor.authorDuyar, Ayse Inan
dc.contributor.authorSunbul, Ali Burak
dc.contributor.authorSerin, Sumeyya
dc.contributor.authorUlu, Oznur Dogan
dc.contributor.authorOzdemir, Ismail
dc.contributor.authorIkiz, Mesut
dc.contributor.authorKose, Muhammet
dc.date.accessioned2026-04-04T13:34:54Z
dc.date.available2026-04-04T13:34:54Z
dc.date.issued2025
dc.departmentİnönü Üniversitesi
dc.description.abstractA series of azobenzene-bearing Schiff base ligands, 4-((E)-(4-ethylphenyl)diazenyl)-2-((E)-(p-tolylimino)methyl) phenol (2), 4-((E)-(4-ethylphenyl)diazenyl)-2-((E)-((4-methoxyphenyl)imino)methyl)phenol (3), 2-((E)-((3,4dimethoxyphenyl)imino)methyl)-4-((E)-(4-ethylphenyl)diazenyl)phenol (4), 2-((E)-((4-chlorophenyl)imino) methyl)-4-((E)-(4-ethylphenyl)diazenyl)phenol (5), 2-((E)-((4-bromophenyl)imino)methyl)-4-((E)-(4-ethylphenyl)diazenyl)phenol (6), 2-((E)-(tert-butylimino)methyl)-4-((E)-(4-ethylphenyl)diazenyl)phenol (7), 2-((E)(cyclohexylimino)methyl)-4-((E)-(4-ethylphenyl)diazenyl)phenol (8) and their homoleptic Pd(II) complexes have been synthesized. Ligand structures were characterized by the combination of 13CNMR , 1HNMR , FTIR, UV-Visible spectroscopy and elemental analyses. According to the UV-visible, FTIR, elemental analyses and HRMS data, the Pd(II) complexes 9-15 are formed by the coordination of N, O atoms of the ligands. Examining the coordination of the free ligands with the central metal ion, the new weak bands observed in the 633-581 and 543-481 cm-1 ranges in the spectra of the Pd(II) metal complexes can be attributed to M-O and M-N stretching peaks, respectively. DFT calculations were performed to determine the optimized structures of Pd(II) complexes utilizing the GAUSSIAN 16 software package with appropriate basis sets. The HOMO and LUMO energies of complexes 9-15 were calculated at the studied theory level in the gas phase. The Delta E values were found to be 3.136-3.239 eV range suggests the high chemical reactivity for those of Pd(II) complexes. In addition, Pd(II) complexes were used as catalysts for Suzuki-Miyaura coupling reactions of phenylboronic acid with aryl bromide in aqueous media. All complexes exhibited notably high catalytic properties in the Suzuki-Miyaura coupling reactions. It was found that the substit & uuml;e groups in the aryl bromide has an impact on the catalytic reaction. In the presence of an electron-withdrawing group such as 4-bromobenzaldehyde, the highest yields were obtained with catalysts 12 and 15, while the lowest yield was observed when catalyst 11 was used with 86 % efficiency.
dc.description.sponsorshipUnit of Coordination of Scientific Research Projects, Kahramanmaras, Sutcu Imam University, Kahramanmaras, Turkey [2023/4-8 M]; Scientific and Technological Research Application and Research Center, Sinop University, Turkey
dc.description.sponsorshipThis work was financially supported by the Unit of Coordination of Scientific Research Projects, Kahramanmaras, Sutcu Imam University, Kahramanmaras, Turkey (Project no: 2023/4-8 M). The authors acknowledge Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer and Central Laboratory, METU, Turkey, for the use of the Waters Synapt G1 instrument. The numerical calculations reported in this paper were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).
dc.identifier.doi10.1016/j.molstruc.2024.141296
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.orcid0000-0002-5561-227X
dc.identifier.orcid0000-0001-6325-0216
dc.identifier.orcid0000-0002-4637-1734
dc.identifier.orcid0000-0001-8681-9858
dc.identifier.scopus2-s2.0-85214299397
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2024.141296
dc.identifier.urihttps://hdl.handle.net/11616/109486
dc.identifier.volume1328
dc.identifier.wosWOS:001414567300001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250329
dc.subjectAzo-azomethine
dc.subjectPd(II) complexes
dc.subjectSuzuki-miyaura coupling
dc.subjectC-C bond formation
dc.titleSynthesis, characterization, DFT quantum chemical calculations and catalytic properties of azobenzene-bearing Schiff base palladium(II) complexes for the Suzuki-Miyaura Cross-Coupling reaction in aqueous solvent
dc.typeArticle

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