Palladium(II) and platinum(II) complexes of a new imineoxime ligand – Structural, spectroscopic and DFT/time-dependent (TD) DFT studies

Kaya, Yunus; İçsel, Ceyda; Yılmaz, Veysel T.; Büyükgüngör, Orhan

doi:10.1016/j.jorganchem.2013.12.011

Cited by 20 publications

(22 citation statements)

References 67 publications

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“…Therefore, the optimized molecular structure of the most stable isomer ( s ‐ trans ‐( E , E )) is used for all calculations. Similar calculations were also made for Ib in our previous study . Tautomers are structural isomers that are conceptually related by the shift of hydrogen and one or more bonds.…”

Section: Resultssupporting

confidence: 85%

“…Compound IIa was obtained as a single crystal, while compound Ia and Ib were synthesized as a polycrystalline powder. Thus, the structures of Ia and Ib were supported by spectroscopic methods and LC/MS technique . In this study, the reaction mechanisms of inapH with pea and ea, and rearrangement of compounds Ia and Ib were studied theoretically.…”

Section: Resultssupporting

confidence: 54%

“…After separating the oxiimine alcohol ( Ia ) from the reaction mixture, the filtrate was evaporated, and then the oily product was recrystallized, so the unexpected product, amido alcohol ( IIa ), was obtained at very low yield (9%). In addition, as a result of the reaction of inapH with ethanol amine (ea) only oxiimine alcohol ( Ib ), namely (1 E ,2 E )‐[(2‐hydroxyethyl)imino]‐2‐phenylethanal oxime was synthesized (yield, 87%) and amido alcohol ( IIb ) could not be obtained . Compound IIa was obtained as a single crystal, while compound Ia and Ib were synthesized as a polycrystalline powder.…”

Section: Resultsmentioning

confidence: 96%

“…Recently, we synthesized oxiimine alcohols, namely (3 E )‐3‐aza‐5‐(hydroxyimino)‐1,4‐diphenylpent‐3‐en‐1‐ol ( Ia ) and (1 E ,2 E )‐[(2‐hydroxyethyl)imino]‐2‐phenylethanal oxime ( Ib ) . During the preparation of the compound Ia , we observed that the amido alcohol ( IIa ) was obtained as associated product interestingly.…”

Section: Introductionmentioning

confidence: 99%

“…The amido alcohol ( IIa ) was characterized by single‐crystal X‐ray diffraction . But the compound IIb could not be obtained in the synthesis of compound Ib . The aim of this work is to study the formation mechanism of oxiimine alcohols, namely Ia and Ib .…”

Section: Introductionmentioning

confidence: 99%

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Density Functional Study of the Reaction Mechanism of Two Oxiimine Alcohol Formations and Their Novel Rearrangements

Kaya

2016

Helvetica Chimica Acta

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In this study, the reaction mechanisms of isonitrosoacetophenone (inapH) with ethanolamine (ea) and 1‐phenylethanolamine (pea) have been investigated theoretically using B3LYP/6‐311G(d,p) method to explain why the formation and unexpected rearrangement products occur or not occur. While the reaction between isonitrosoacetophenone (inapH) with ethanolamine gives oximine alcohol (Ib), the reaction of 1‐phenylethanolamine with inapH results in the formation of oximine alcohol with a different substituent (Ia) and amido alcohol (IIa), which is the unexpected rearrangement product. The rearrangement driving forces of compounds from Ia to IIa are calculated as ca. 28 and 23 kJ/mol in the gas and EtOH phases, respectively. These driving forces have been calculated ca. 46 and 45 kJ/mol for the rearrangement of compound Ib to obtain IIb in the same phases, respectively. This high driving force shows that the compound IIb cannot be obtained from rearrangement of compound Ib as described experimentally in the literature. In addition, as the DFT functionals poorly describe dispersion effects, dispersion correction for reaction heat and free‐energy barrier was estimated using the wB97X‐D/6‐311G(d,p). In general, the relative free energies of all molecules calculated from wB97XD method are lower than performed from B3LYP level. The changes of thermodynamic properties for all molecules with temperature ranging from 100 to 500 K have been obtained using the statistical thermodynamic method.

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Section: Resultssupporting

confidence: 85%

Section: Resultssupporting

confidence: 54%

Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Density Functional Study of the Reaction Mechanism of Two Oxiimine Alcohol Formations and Their Novel Rearrangements

Kaya

2016

Helvetica Chimica Acta

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Improvement of Solid Photoluminescence of Tridentate Schiff Base Pt(II) Foldamer by Hybridizing Poly (4‐Vinylpyridine)

et al. 2022

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A series of bis(tridentate Schiff base platinum) complex (Pt 2 L 2 ) linked with 2-methylenepropane-1,3-diyl were synthesized, and their photophysical properties were examined to analyze different solid states. X-ray crystallographic analysis indicated that Pt 2 L 2 containing 4-vinylpyridine (Pt 2 L 2 4VP) as a ligand had a helically-folded structure. It caused upfield chemical shifts and a redshift in UV-Vis absorption spectra compared to the analogous mononuclear complex. Pt 2 L 2 containing dimethylsulfoxide (Pt 2 L 2 DMSO) had no such helically-folded structure due to the steric repulsion of DMSO. Pt 2 L 2 4VP did not exhibit solid photoluminescence owing to the crystal packing. The mixture of poly(4-vinylpyridine) (P4VP) and Pt 2 L 2 DMSO (Pt 2 L 2 DMSOÀ P4VP) showed a similar redshift in UV-Vis absorption and excitation spectra to Pt 2 L 2 4VP, implying the helically-folded structure of Pt 2 L 2 with P4VP coordination. The Pt 2 L 2 DMSOÀ P4VP exhibited solid photoluminescence with a longer phosphorescence lifetime (2.4 μs) than the Pt 2 L 2 4VP crystals (0.5 μs), indicating regulated aggregation of the Pt 2 L 2 frames in the P4VP matrix.

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Photodegradation of 2,4-dichlorophenol by supported Pd(X2) catalyst (X = Cl, Br, N3): a HOMO manipulating point of view

Nejad

Shahrnoy

Mahjoub

et al. 2018

Environ Sci Pollut Res

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Three different palladium(II) complexes with ligands containing nitrogenized aromatic rings were investigated theoretically as model to obtain the computational band gap energies. The results demonstrated promising possibility for designing palladium(II) complexes with photocatalytic properties at visible light irradiation. Deliberated products were synthesized via grafting on the silica-coated FeO magnetic nanoparticles (FeO@SiO). Formation of complexes on the surface of FeO@SiO, as insoluble and reusable photocatalysts, was proved by Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), thermogravimetric (TGA), X-ray photoelectron spectroscopy (XPS), vibrating sample magnetometer (VSM), transmission electron microscope (TEM), and scanning electron microscopy (SEM) analyses. The trend of the band gap energies of prepared structures was calculated via experimental and theoretical methods. The photocatalytic capability of these nanoparticles was investigated in degradation of 2,4-dichlorophenol by means of HPLC analysis. A tentative reaction mechanism for the formation of intermediates was proposed. Graphical abstract ᅟ.

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Palladium(II) and platinum(II) complexes of a new imineoxime ligand – Structural, spectroscopic and DFT/time-dependent (TD) DFT studies

Cited by 20 publications

References 67 publications

Density Functional Study of the Reaction Mechanism of Two Oxiimine Alcohol Formations and Their Novel Rearrangements

Density Functional Study of the Reaction Mechanism of Two Oxiimine Alcohol Formations and Their Novel Rearrangements

Improvement of Solid Photoluminescence of Tridentate Schiff Base Pt(II) Foldamer by Hybridizing Poly (4‐Vinylpyridine)

Photodegradation of 2,4-dichlorophenol by supported Pd(X2) catalyst (X = Cl, Br, N3): a HOMO manipulating point of view

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