Research Article
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Year 2017, Volume: 18 Issue: 3, 640 - 653, 30.09.2017
https://doi.org/10.18038/aubtda.292591

Abstract

References

  • Chakravorty A. Structural chemistry of transition metal complexes of oximes. Coord Chem Rev 1974; 13: 1-46.
  • Deveci P, Taner B, Kılıc Z, Solak, AO, Arslan U, Özcan E. Synthesis, electrochemical and structural characterization of novel azacrown ether containing macrocyclic redox-active vic-dioxime ligand and its mononuclear transition metal complexes: Application of DEPT, HSQC, HMBC-NMR and cyclic voltammetry. Polyhedron 2011; 30: 1726–1731.
  • Moon S, Case DA. A comparison of quantum chemical models for calculating NMR shielding parameters in peptides: Mixed basis set and ONIOM methods combined with a complete basis set extrapolation. J Comput Chem 2006; 27(7): 825-836.
  • Brandenburg JG, Maas T, Grimmea S. Benchmarking DFT and semiempirical methods on structures and lattice energies for ten ice polymorphs. J Chem Phys 2015; 142: 124104-1-124104-11.
  • Matczak P. Assessment of various density functionals for intermolecular NSn interactions: The test case of poly(trimethyltin cyanide). Comput Theor Chem 2015; 1051: 110-122.
  • Li L, Zhang S, Zhang JSH, He X. Assessing the performance of popular QM methods for calculation of conformational energies of trialanine. Chem Phys Lett 2016; 652:136–141.
  • Antonov L, Kurteva V. Tautomerism in 1-phenylazo-4-naphthols: Experimental results vs quantum-chemical predictions. Dyes Pigm 2011; 92: 714-723.
  • Pisani C. Local techniques for the ab initio quantum-mechanical description of the chemical properties of crystalline materials. J Mol Struct 2003; 621: 141-147.
  • Kaya Y, Icsel C, Yilmaz VT, Buyukgungor O. A palladium(II) complex containing both carbonyl and imine oxime ligands: Crystal structure, experimental and theoretical UV–vis, IR and NMR studies. Spectrochim Acta Part A 2013; 108: 133-140.
  • Zülfikaroğlu A, Taş M, Batı H, Batı B. The synthesis and characterization of substituted aminomethylglyoximes and amino phenylglyoximes and their complexes with some transition metals. Synth React Inorg Met Org Chem 2003; 33(4): 625–638.
  • Hökelek T, Zülfikaroğlu A, Batı H. 1-(2,6-Dimethylphenylamino)propane-1,2-dione dioxime. Acta Cryst 2001; E57: o1247-o1249.
  • Batı H, Zülfikaroğlu A, Taş M, Andaç Ö, Harrison WTA. Bis[1-(2,6-dimethylanilino)propane-1,2-dione dioximato]nickel(II). Acta Cryst 2005; E61: m2033-m2035.
  • Sakıyama H, Oshima M, Suzuki S, Nishida Y. Several Molecular Orbital Computations for a Dinuclear Nickel(II) Complex. Compt Chem Jpn 2009; 8(2): 87-92.
  • Reed AE, Curtiss LA, Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev 1988; 88(6): 899-926.
  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria G.E, Robb MA, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, et al. Gaussian 09, Revision C.01; Gaussian, Inc.: Wallingford, CT, 2009.
  • Dennington, R.; Keith, T.; Millam, J. GaussView, Version 5; Semichem Inc.: Shawnee Mission, KS, 2009.
  • Kohn W, Becke AD, Parr RG. Density Functional Theory of Electronic Structure. J. Phys. Chem 1996; 100: 12974-12980.
  • Becke AD. Density‐functional thermochemistry. III. The role of exact Exchange. J Chem Phys 1993; 98(7): 5648-5652.
  • Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 1988; 38: 3098-3010.
  • Peng C, Ayala PY, Schlegel HB, Frisch MJ. Using Redundant Internal Coordinates to Optimize Equilibrium Geometries and Transition States. J Comput Chem 1996, 17(1): 49-56.
  • Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP. AM1: A New General Purpose Quantum Mechanical Molecular Model. J Amer Chem Soc 1985; 107: 3902-3909.
  • Stewart JJP. Optimizationof parameters of semiempirical methods I. Method. J Comput Chem 1989; 10(2): 209-220.
  • Stewart JJP. Optimization of parameters for semiempirical methods V: Modification of NDDO approximations and application. J Mol Model 2007; 13: 1173–1213.
  • Wolinski K, Hinton J, Pulay P. Efficient implementation of the gaugeindependent atomic orbital method for NMR chemical shift calculations. J Amer Chem Soc 1990; 112: 8251-8260.
  • Runge E, Gross EKU. Density-Functional Theory for Time-Dependent Systems. Phys Rev Lett 1984; 52: 997-1000.
  • Bauernschmitt R, Ahlrichs R. Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem Phys Letter 1996; 256: 454-464.
  • Glendening ED, Reed AE, Carpenter JE, Weinhold F. NBO Version 3.1, TCI, University of Wisconsin, Madison, 1998.
  • Gül A, Bekaroğlu Ö. Syntheses of N,N’-bis(4’-benzo[15-crown-5]- diamino-glyoxime and its complexes with copper(II), nickel(II), cobalt( III)–palladium(II), platinum(II) and uranyl(VI). J Chem Soc Dalton Trans 1983; 2537-2541.
  • Sevindir HC, Ersöz M, Mirzaoğlu R. The synthesis of three unsymetrical vic-dioximes and their complexes with some transition metals. Synth. React. Inorg. Met.-Org. Chem 1994; 24(3): 419-426.
  • Deveci MA, İrez G, Mercimek B, Bedük AD, Sarıkavaklı N. The synthesis and Ni(II), Co(II) and Cu(II) complexes of three new unsymmetrical vic-dioxime. Synth React Inorg Met.-Org Chem 1995; 25(10): 1699-1706.
  • Kowalczyk I, Bartoszak-Adamska E, Jaskolski M, Dega-Szafran Z, Szafran M. Structure of 1H-2-oxo-2,3-dihydroimidazo[1,2-a]pyridinium perchlorate studied by X-ray diffraction, DFT calculations and by FTIR and NMR spectroscopy 2010. Journal of Molecular Structure, 976(2010), 119-128.
  • Gorelsky SI. SWizard Program Revision 4.5, University of Ottawa, Ottawa, 2010.
  • Kaya Y, Icsel C, Yilmaz VT, Buyukgungor O. Palladium(II) and platinum(II) complexes of a new imineoxime ligand: Structural, spectroscopic and DFT/time dependent (TD) DFT studies. J.Org. Met. Chem 2014; 752: 83-90.
  • Kaya Y, Yilmaz VT, Taner A, Buyukgungor O. Experimental and theoretical DFT studies of structure, spectroscopic and fluorescence properties of a new imine oxime derivative. J Mol Struct 2012; 1024: 65-72.

Quantum Chemical Computational Studies on a vic-Dioxime Ligand and Its Nickel Complex

Year 2017, Volume: 18 Issue: 3, 640 - 653, 30.09.2017
https://doi.org/10.18038/aubtda.292591

Abstract

In this study, the structural and bonding
characteristic of
1-(2,6-Dimethylphenylamino)propane-1,2-dione
dioxime ligand and its nickel(II) complex
were examined by
means of quantum chemical computations. Primarily, comprehensive calculations
were performed on these compounds at the DFT, HF and semi-empirical levels of
theory by using different basis sets. The structural accuracy of ligand and
complex were investigated by comparing the calculated values to the bond
lengths and angles measured in X-ray structures. Then, comparison of the
methods was applied by considering quality factors calculated for different
basis sets of each method.
The theoretical
structural studies on ligand and complex were carried out by UV-Vis, FT-IR and
NMR spectral analysis. The calculated vibrational bands,
electronic absorption spectrum and NMR chemical shifts were determined to be consistent with the
experimental results. In additional, the characteristic of the metal-ligand
interactions were demonstrated by natural bond orbital (NBO) analysis.

References

  • Chakravorty A. Structural chemistry of transition metal complexes of oximes. Coord Chem Rev 1974; 13: 1-46.
  • Deveci P, Taner B, Kılıc Z, Solak, AO, Arslan U, Özcan E. Synthesis, electrochemical and structural characterization of novel azacrown ether containing macrocyclic redox-active vic-dioxime ligand and its mononuclear transition metal complexes: Application of DEPT, HSQC, HMBC-NMR and cyclic voltammetry. Polyhedron 2011; 30: 1726–1731.
  • Moon S, Case DA. A comparison of quantum chemical models for calculating NMR shielding parameters in peptides: Mixed basis set and ONIOM methods combined with a complete basis set extrapolation. J Comput Chem 2006; 27(7): 825-836.
  • Brandenburg JG, Maas T, Grimmea S. Benchmarking DFT and semiempirical methods on structures and lattice energies for ten ice polymorphs. J Chem Phys 2015; 142: 124104-1-124104-11.
  • Matczak P. Assessment of various density functionals for intermolecular NSn interactions: The test case of poly(trimethyltin cyanide). Comput Theor Chem 2015; 1051: 110-122.
  • Li L, Zhang S, Zhang JSH, He X. Assessing the performance of popular QM methods for calculation of conformational energies of trialanine. Chem Phys Lett 2016; 652:136–141.
  • Antonov L, Kurteva V. Tautomerism in 1-phenylazo-4-naphthols: Experimental results vs quantum-chemical predictions. Dyes Pigm 2011; 92: 714-723.
  • Pisani C. Local techniques for the ab initio quantum-mechanical description of the chemical properties of crystalline materials. J Mol Struct 2003; 621: 141-147.
  • Kaya Y, Icsel C, Yilmaz VT, Buyukgungor O. A palladium(II) complex containing both carbonyl and imine oxime ligands: Crystal structure, experimental and theoretical UV–vis, IR and NMR studies. Spectrochim Acta Part A 2013; 108: 133-140.
  • Zülfikaroğlu A, Taş M, Batı H, Batı B. The synthesis and characterization of substituted aminomethylglyoximes and amino phenylglyoximes and their complexes with some transition metals. Synth React Inorg Met Org Chem 2003; 33(4): 625–638.
  • Hökelek T, Zülfikaroğlu A, Batı H. 1-(2,6-Dimethylphenylamino)propane-1,2-dione dioxime. Acta Cryst 2001; E57: o1247-o1249.
  • Batı H, Zülfikaroğlu A, Taş M, Andaç Ö, Harrison WTA. Bis[1-(2,6-dimethylanilino)propane-1,2-dione dioximato]nickel(II). Acta Cryst 2005; E61: m2033-m2035.
  • Sakıyama H, Oshima M, Suzuki S, Nishida Y. Several Molecular Orbital Computations for a Dinuclear Nickel(II) Complex. Compt Chem Jpn 2009; 8(2): 87-92.
  • Reed AE, Curtiss LA, Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev 1988; 88(6): 899-926.
  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria G.E, Robb MA, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, et al. Gaussian 09, Revision C.01; Gaussian, Inc.: Wallingford, CT, 2009.
  • Dennington, R.; Keith, T.; Millam, J. GaussView, Version 5; Semichem Inc.: Shawnee Mission, KS, 2009.
  • Kohn W, Becke AD, Parr RG. Density Functional Theory of Electronic Structure. J. Phys. Chem 1996; 100: 12974-12980.
  • Becke AD. Density‐functional thermochemistry. III. The role of exact Exchange. J Chem Phys 1993; 98(7): 5648-5652.
  • Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 1988; 38: 3098-3010.
  • Peng C, Ayala PY, Schlegel HB, Frisch MJ. Using Redundant Internal Coordinates to Optimize Equilibrium Geometries and Transition States. J Comput Chem 1996, 17(1): 49-56.
  • Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP. AM1: A New General Purpose Quantum Mechanical Molecular Model. J Amer Chem Soc 1985; 107: 3902-3909.
  • Stewart JJP. Optimizationof parameters of semiempirical methods I. Method. J Comput Chem 1989; 10(2): 209-220.
  • Stewart JJP. Optimization of parameters for semiempirical methods V: Modification of NDDO approximations and application. J Mol Model 2007; 13: 1173–1213.
  • Wolinski K, Hinton J, Pulay P. Efficient implementation of the gaugeindependent atomic orbital method for NMR chemical shift calculations. J Amer Chem Soc 1990; 112: 8251-8260.
  • Runge E, Gross EKU. Density-Functional Theory for Time-Dependent Systems. Phys Rev Lett 1984; 52: 997-1000.
  • Bauernschmitt R, Ahlrichs R. Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem Phys Letter 1996; 256: 454-464.
  • Glendening ED, Reed AE, Carpenter JE, Weinhold F. NBO Version 3.1, TCI, University of Wisconsin, Madison, 1998.
  • Gül A, Bekaroğlu Ö. Syntheses of N,N’-bis(4’-benzo[15-crown-5]- diamino-glyoxime and its complexes with copper(II), nickel(II), cobalt( III)–palladium(II), platinum(II) and uranyl(VI). J Chem Soc Dalton Trans 1983; 2537-2541.
  • Sevindir HC, Ersöz M, Mirzaoğlu R. The synthesis of three unsymetrical vic-dioximes and their complexes with some transition metals. Synth. React. Inorg. Met.-Org. Chem 1994; 24(3): 419-426.
  • Deveci MA, İrez G, Mercimek B, Bedük AD, Sarıkavaklı N. The synthesis and Ni(II), Co(II) and Cu(II) complexes of three new unsymmetrical vic-dioxime. Synth React Inorg Met.-Org Chem 1995; 25(10): 1699-1706.
  • Kowalczyk I, Bartoszak-Adamska E, Jaskolski M, Dega-Szafran Z, Szafran M. Structure of 1H-2-oxo-2,3-dihydroimidazo[1,2-a]pyridinium perchlorate studied by X-ray diffraction, DFT calculations and by FTIR and NMR spectroscopy 2010. Journal of Molecular Structure, 976(2010), 119-128.
  • Gorelsky SI. SWizard Program Revision 4.5, University of Ottawa, Ottawa, 2010.
  • Kaya Y, Icsel C, Yilmaz VT, Buyukgungor O. Palladium(II) and platinum(II) complexes of a new imineoxime ligand: Structural, spectroscopic and DFT/time dependent (TD) DFT studies. J.Org. Met. Chem 2014; 752: 83-90.
  • Kaya Y, Yilmaz VT, Taner A, Buyukgungor O. Experimental and theoretical DFT studies of structure, spectroscopic and fluorescence properties of a new imine oxime derivative. J Mol Struct 2012; 1024: 65-72.
There are 34 citations in total.

Details

Subjects Engineering
Journal Section Articles
Authors

Ayşin Zülfikaroğlu

Publication Date September 30, 2017
Published in Issue Year 2017 Volume: 18 Issue: 3

Cite

APA Zülfikaroğlu, A. (2017). Quantum Chemical Computational Studies on a vic-Dioxime Ligand and Its Nickel Complex. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 18(3), 640-653. https://doi.org/10.18038/aubtda.292591
AMA Zülfikaroğlu A. Quantum Chemical Computational Studies on a vic-Dioxime Ligand and Its Nickel Complex. AUJST-A. September 2017;18(3):640-653. doi:10.18038/aubtda.292591
Chicago Zülfikaroğlu, Ayşin. “Quantum Chemical Computational Studies on a Vic-Dioxime Ligand and Its Nickel Complex”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 18, no. 3 (September 2017): 640-53. https://doi.org/10.18038/aubtda.292591.
EndNote Zülfikaroğlu A (September 1, 2017) Quantum Chemical Computational Studies on a vic-Dioxime Ligand and Its Nickel Complex. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 18 3 640–653.
IEEE A. Zülfikaroğlu, “Quantum Chemical Computational Studies on a vic-Dioxime Ligand and Its Nickel Complex”, AUJST-A, vol. 18, no. 3, pp. 640–653, 2017, doi: 10.18038/aubtda.292591.
ISNAD Zülfikaroğlu, Ayşin. “Quantum Chemical Computational Studies on a Vic-Dioxime Ligand and Its Nickel Complex”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 18/3 (September 2017), 640-653. https://doi.org/10.18038/aubtda.292591.
JAMA Zülfikaroğlu A. Quantum Chemical Computational Studies on a vic-Dioxime Ligand and Its Nickel Complex. AUJST-A. 2017;18:640–653.
MLA Zülfikaroğlu, Ayşin. “Quantum Chemical Computational Studies on a Vic-Dioxime Ligand and Its Nickel Complex”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, vol. 18, no. 3, 2017, pp. 640-53, doi:10.18038/aubtda.292591.
Vancouver Zülfikaroğlu A. Quantum Chemical Computational Studies on a vic-Dioxime Ligand and Its Nickel Complex. AUJST-A. 2017;18(3):640-53.