79
80
Diğer bir uygulama hesaplama maliyetini arttırmayan empirik dispersiyon düzeltme yaklaşımlarının bu moleküler sistemlerdeki hesaplamalar üzerine etkisinin irdelenmesi olmuştur. Sonuçlara göre fonksiyonellerin çok farklı bant genişlikleri değerleri sunabildikleri, geometrik parametreler açısında menzil-ayrımlı hibrit fonksiyonellerin daha başarılı olduğu, empirik düzeltme yaklaşımlarının kullanılmasının geometrik parametreler üzerinde istatistiksel olarak olumlu etki yaptığı buna karşılık HOMO-LUMO enerji değerleri üzerinde anlamlı değişiklik yaratamadığı belirlenmiştir. Teorik
1H-NMR ve 13C-NMR verileri incelendiğinde en başarılı fonksiyonelin B3LYP olduğu performansı en düşük olan fonksiyonellerin ise hibrit olmayan fonksiyoneller olduğu belirlenmiştir. Empirik dispersiyon düzeltme yaklaşımlarının ise teorik 1H-NMR verileri üzerinde belirgin bir fark yaratmasa da teorik 13C-NMR verilerini olumsuz olarak etkilemekte olduğu yani hesap kalitesini düşürdüğü belirlenmiştir.
Teorik kutuplanabilirlik çalışmaları sonucunda bulunan orta ve iyi derecedeki hiperkutuplanabilirlik değerleri literatür değerleri ile karşılaştırıldığında ONO verici uçlu ligantlardan elde edilmiş söz konusu beş koordinasyonlu diorganokalay(IV) komplekslerinin doğrusal olmayan optik materyaller olarak kullanım alanı bulabilecekleri sonucuna da varılmıştır.
Tez kapsamında elde edilmiş tüm sonuçlar sırasıyla 2014 yılında Applied Organometallic Chemistry ve 2015 yılında da Journal of Molecular Modelling dergilerinde yayınlanmak suretiyle literatüre kazandırılmıştır.
81 KAYNAKLAR
Abraham, J.P., Sajan, D., Shettigar, V., Dharmaprakash, S.M., Nemec, I., Joe, I.H. and Jayakumar, V.S. 2003. Efficient p-electron conjugated push–pull nonlinear optical chromophore 1-(4-methoxyphenyl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one:a vibrational spectral study. Journal of Molecular Structure, 917, 27-36.
Addison, A.W., Rao, T.N., Reedijk, J., Van Rijn, J. and Verschoor, G.C. 1984.
Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen–sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane]copper(II)
perchlorate. Journal of Chemical Society, Dalton Transactions, 7, 1349-1356.
Aliev, A.E., Courtier-Murias, D. and Zhou, S. 2009. Scaling factors for carbon NMR chemical shifts obtained from DFT B3LYP calculations. Journal of Molecular Structure-Theochem, 893, 1-5.
Alipour, M. and Mohajeri, A. 2013. Assessing the performance of density functional theory for the dynamic polarizabilities of amino acids: treatment of correlation and role of exact exchange. International Journal of Quantum Chemistry, 113, 1803-1811.
Ancın, N., Öztaş, S.G. and İde, S. 2007. Synthesis and characterization of diorganotin(IV) complexes of tridentate Schiff bases: crystal structure of [N-(3-hydroxypyridine-2-yl)-5-chlorosalicylideneiminato]dimethyltin(IV). Structural Chemistry, 18, 667-675.
Andersson, M.P. and Uvdal, P. 2005. New scale factors for harmonic vibrational frequencies using the B3LYP density functional method with the triple-zeta basis set 6–311+G(d,p). Journal of Physical Chemistry A, 109, 2937-2941.
Avcı, D., Cömert, H. and Atalay, Y. 2008. Ab initio Hartree-Fock calculations on linear and second-order nonlinear optical properties of new acridine-benzothiazolylamine chromophores. Journal of Molecular Modelling, 14, 161-169.
Bagno, A., Casella, G., Ferrante, F. and Saielli, G. 2013. A DFT study of the vicinal
3J(119Sn,13C) and 3J(119Sn,1H) coupling constants in trimethyl- and chlorodimethylstannyl propanoates. Journal of Organometalic Chemistry 724, 139-146.
Bagno, A., Rastrelli, F. and Saielli, G. 2006. Toward the complete prediction of the 1H and 13C NMR spectra of complex organic molecules by DFT methods:
application to natural substances. Chemistry European Journal, 12, 5514-5525.
82
Baird, N.C. and Dewar, M.J.S. 1969. Ground States of σ‐Bonded Molecules. IV. The MINDO Method and Its Application to Hydrocarbons. Journal of Chemical Physics, 50, 1262-1274.
Barone, V., Bencini, A., Totti, F. and Uytterheoven, M.G. 1997. Comparison between post-Hartree-Fock and DFT methods for the study of strength and mechanism of cleavage of Hg-C bond. International Journal of Quantum Chemistry, 61, 361-367.
Bauer, A.W., Kirby, W.M. Sherris, J.C. and Turck, M. 1966. Antibiotic susceptibility testing by a standardized single disk method. American Journal of Clinical Pathology, 45, 493.
Beattie, R.M., McQuillan, G. P. and Hulme, R. 1962. Chemistry and Industry, 1429.
Becke A.D. 1993. Density-functional thermochemistry. III. The role of exact exchange.
Journal of Chemical. Physics, 98, 5648-5452.
Becke, A.D. 1988. Density-functional exchange-energy approximation with correct asymptotic-behavior. Physical Review A, 38, 3098-3100.
Beltrán, H.I., Damian-Zea, C., Ortega, S.H., Camacho, A.N. and Apan, M.T.R. 2007.
Synthesis and characterization of di-phenyl-tinIV -salicyliden-ortho-aminophenols: Analysis of in vitro antitumor/antioxidant activities and molecular structures. Journal of Inorganic Biochemistry, 101, 1070-1085.
Beltrán, H.I., Zamudio-Rivera, L.S., Mancilla, T., Santillan, R. and Farfan, N. 2003.
One-Step Preparation, Structural Assignment, and Xray Study of 2,2-Di-n-butyl- and 2,2-Diphenyl-6-aza-1,3-dioxa-2-stannabenzocyclononen-4-ones Derived from Amino Acids. Chemistry A European Journal, 9, 2291-2306.
Boese A.D. and Handy, N.C. 2001 A new parametrization of exchangecorrelation generalized gradient approximation functionals. Journal of Chemical Physics 114:5497-5503.
Boese, A.D. and Martin, J.M.L. 2003. The role of the basis set: assessing density functional theory. Journal of Chemical Physics, 119, 3005-3014.
Bygrave, P.J., Case, D.H. and Day, G.M. 2014. Is the equilibrium composition of mechanochemical reactions predictable using computational chemistry? Faraday Discussions, 170, 41-57.
Cardarelli, N.F. 1968. US Patent 3 417 181.
Castro, L., Kirillov, E., Miserque, O., Welle, A., Haspeslagh, L., Carpentier, J.F. and Maron, L. 2015. Are Solvent and Dispersion Effects Crucial in Olefin Polymerization DFT Calculations? Some Insights from Propylene Coordination
83
and Insertion Reactions with Group 3 and 4 Metallocenes. ACS Catalysis, 5, 416-425.
Chai, J.D. and Gordon, M.H. 2008. Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Physical Chemistry Chemical Physics, 10, 6615-6620.
Check, C.E., Faust, T.O., Bailey, J.M., Wright, B.J., Gilbert, T.M. and Sunderlin, L.S.
2001. Addition of polarization and diffuse functions to the lanl2dz basis set for P-block elements. Journal of Physical Chemistry A, 105, 8111-8116.
Cheeseman, J.R., Trucks, G.W., Keith, T.A. and Frisch, M.J. 1996. A Comparison of Models for Calculating Nuclear Magnetic Resonance Shielding Tensors. Journal of Chemical Physics, 104, 5497-5509.
Chemla, D.S. and Zyss, J. 1987. Nonlinear Optical Properties of Organic Molecules and Crystals. Academic Press, 482, Orlando.
Cizek, J. 1966. On the Correlation Problem in Atomic and Molecular Systems.
Calculation of Wavefunction Components in Ursell‐Type Expansion Using Quantum‐Field Theoretical Methods. Journal of Chemical Physics, 45, 4256-4266.
Cramer, C.C. 2004. Essentials of Computational Chemistry Theories and Models, 2nd Edition. John Wiley & Sons, Ltd, 618, England.
Creaven, B.S., Devereux, M., Foltyn, A., McClean, S., Rosair, G., Thangella, V.R. and Walsh, M. 2010. Quinolin-2(1H)-one-triazole derived Schiff bases and their Cu(II) and Zn(II) complexes: Possible new therapeutic agents. Polyhedron, 29, 813-822.
Çelebier, M., Şahin, E., Ancın, N., Öztaş, N.A. and Öztaş, S.G. 2007. Synthesis and characterization of diorganotin(IV) complexes of Schiff bases with ONO-type donors and crystal structure of [N-(2-hydroxy-4-nitrophenyl)-3-ethoxysalicylideneiminato] diphenyltin(IV). Applied Organometallic Chemistry, 21, 913-918.
Dakternieks, D., Baul, T.S.B., Dutta, S. and Tiekink, E.R.T. 1998. Synthesis, Characterization, and X-ray Structures of Diphenyltin(IV) N-(2-Hydroxyacetophenone)glycinate, Its 1:1 Adduct with Triphenyltin(IV) Chloride, and Related Systems. Organometallics, 17, 3058-3062.
Davies, A.G. 2004. Organotin Chemistry, 2nd edn, Wiley-VCH, 438, Weinheim.
Dewar, M.J.S. and Thiel, W. 1977. Ground states of molecules. 38. The MNDO method. Approximations and parameters. Journal of the American Chemical Society, 99, 4899.
84
Dewar, M.J.S., Zoebisch, E.G., Eamonn H.F. and Stewart, J.J.P. 1985. Development and use of quantum mechanical molecular models. 76. AM1: A new general purpose quantum mechanical molecular model. Journal of the American Chemical Society 107, 3902.
Dey, D.K., Dey, S.P, Karan, N.K., Datta, A., Lycka, A. and Rosair, G. 2009. Structural and spectral studies of 3-(2-hydroxyphenylimino)-1-phenylbutan-1-one and its diorganotin(IV) complexes. Journal of Organometallic Chemistry, 694, 2434-2441.
Dey, D.K., Lycka, A., Mitra, S. and Rosair, G.M. 2003. Simplified synthesis, 1H, 13C,
15N, 119Sn NMR spectra and X-ray structures of diorganotin(IV) complexes containing the 4-phenyl-2,4-butanedionebenzoylhydrazone(2−) ligand. Journal of Organometallic Chemistry, 689, 88-95.
Dey, D.K., Saha, M.K., Gielen, M., Kemmer, M., Biesemans, M., Willem, R., GramLich, V. and Mitra, S. 1999. Synthesis, spectroscopy and structure of [N- (2-carboxyphenyl) salicylideneiminato] dimethyltin (IV).Journal of Organometallic Chemistry, 590, 88-92.
Dokorou, V., Kovala-Demertzi, D., Jasinski, J.P., Galani, A. and Demertzis, M.A. 2004.
Synthesis, Spectroscopic Studies, and Crystal Structures of Phenylorganotin Derivatives with [Bis (2,6-dimethylphenyl)amino] benzoic Acid: Novel Antituberculosis Agents. Helvetica Chimica Acta, 87, 1940-1950.
Dybiec, K. and Keller, A.G. 2009. Remarks on GIAO-DFT predictions of 13C chemical shifts. Magnetic Resonance Chemistry, 47, 63-66.
Fait, A., Ferioli, A. ve Barbieri, F. 1994. Organotin Compounds. Toxicology, 91(1), 77-82.
Fent, K. 1996. Ecotoxicology of organotin compounds. Critical Review in Toxicology, 26(1), 1-117.
Frankland, E. 1849. Ueber die Isolirung der organischen Radicale. Justus Liebigs Annual Chemie, 71, 171-213.
Frisch, M.J., Gordon, M.H. and Pople, J.A. 1990a. Direct MP2 gradient method.
Chemical Physics Letters, 166, 275-280.
Frisch, M.J., Gordon, M.H. and Pople, J.A. 1990b. Semi-direct algorithms for the MP2 energy and gradient. Chemical Physics Letteer, 166, 281-289.
Fukutome, H. 1981. Unrestricted Hartree–Fock theory and its applications to molecules and chemical reactions. International Journal of Quantum Chemistry, 20(5), 955-1065.
85
Gaballa, A.S., Asker, M.S., Barakat, A.S. and Teleb, S.M. 2007. Synthesis, characterization and biological activity of some platinum(II) complexes with Schiff bases derived from salicylaldehyde, 2-furaldehyde and phenylenediamine.
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 1, 114-121.
Gaussian 09, Revision E.01, Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G.
E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Jr., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J.
B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, R.
L., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J.
J., Dapprich, S., Daniels, A. D., Farkas, Ö., Foresman, J. B., Ortiz, J. V., Cioslowski, J. and Fox, D. J. Gaussian, Inc., Wallingford CT, 2009.
GaussView, Version 5, Dennington, R., Keith, T. and Millam, J. Semichem Inc., Shawnee Mission, KS, 2009.
Gielen, M., Davies, A. G., Pannel, K. and Tiekink, E. 2008. Tin Chemistry:
Fundamentals, Frontiers, and Applications. John Wiley & Sons, 752, United Kingdom.
Glendening, E.D., Reed, A.E., Carpenter, J.E. and Weinhold, F. 1990. NBO, version 3.1. Theoretical Chemistry Institute WISC-TCI, University of Wisconsin-Madison.
Gordon, M.H. and Gordon, T.H. 1994. Analytic MP2 Frequencies Without Fifth Order Storage: Theory and Application to Bifurcated Hydrogen Bonds in the Water Hexamer. Chemical Physics Letters, 220, 122-128.
Gordon, M.H., Pople, J.A., Frisch, M.J. 1988. MP2 energy evaluation by direct methods. Chemical Physics Letters, 153, 503-06.
Grimme, S. 2004. Accurate description of van der Waals complexes by density functional theory including empirical corrections. Journal of Computational Chemisttry, 25, 1463-1473.
Grimme, S. 2006. Semiempirical GGA-type density functional constructed with a long-range dispersion correction. Journal of Computational Chemistry, 27, 1787-1789.
86
Grimme, S., Antony, J., Ehrlich, S. and Krieg, H. 2010. A consistent and accurate ab initio parameterization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. Journal of Chemical Physics, 132, 154104-154119.
Grimme, S., Ehrlich, S. and Goerigk, L. 2011. Effect of the damping function in dispersion corrected density functional theory. Journal of Computational Chemistry, 32, 1456-1465.
Hanwell, M.D., Curtis, D.E., David, C.L., Vandermeersch, T., Zurek, E. and Hutchison, G.R. 2012. Avogadro: An advanced semantic chemical editor, visualization, and analysis platform. Journal of Cheminformatics, 4.
Hay, P.J. and Wadt, W.R. 1985. Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals. The Journal of Chemical Physics, 85, 299.
Hoffmann, A., Rohrmuller, M., Jesser, A., Vieira, I., Schmidt, W.G. and Pawlis, S.H.
2014. Geometrical and Optical Benchmarking of Copper(II) Guanidine–
Quinoline Complexes: Insights from TD-DFT and Many-Body Perturbation Theory (Part II). Journal of Computational Chemistry, 35, 2146-2161.
Hohenberg, P. and Kohn, W. 1964. Inhomogeneous Electron Gas. Physical Reviev, 136, B864-B871.
Holeĉek, J. and Lyĉka, A. 1986. Dependence of 1J(119Sn-13C) on the C-SC angle in n-butyltin(IV) compounds. Inorganica Chimica Acta, 118, L15-L16.
Holm, R.H., Everett, G.W. and Chakravorty, A. 1966. Metal complexes of Schiff bases and β-ketoamines. Progress in Inorganic Chemistry, 7, 83-214.
Hunter, C.A. and Saunders, J.K.M. 1990. The nature of pi-pi interactions. Journal of American Chemical Society, 112, 5525-5534.
Jensen, F. 2007. Introduction to Computational Chemistry 2nd Edition. John Wiley &
Sons, Ltd, 599, United Kingdom.
Jensen, K.P. 2008. Bioinorganic chemistry modeled with the TPSSh density functional.
Inorganic Chemistry, 47, 10357-10365.
Johnson, B.G., Gill, P.M.W. and Pople, J.A. 1993. The performance of a family of density functionalmethods. Journal of Chemical Physics, 98, 5612-5626.
Kajal, A., Bala, S., Kamboj, S., Sharma, N. and Saini, V. 2013. Schiff Bases: A Versatile Pharmacophore. Journal of Catalysts, 13.
Kanis, D.R., Ratner, M.A. and Marks, T.J. 1994. Design and construction of molecular assemblies with large second-order optical nonlinearities. Quantum chemical aspects. Chemical Reviews, 94, 195-242.
87
Kerk, G. J. M. 1976. Organotin Chemistry: Past, Present, and Future, in Organotin Compounds, New Chemistry and Applications. Advances in Chemistry Series 1 57, American Chemical Society, Washington, DC
Khoo, L.E., Xu, Y., Goh, N.K., Chia, L.S. and Koh, L.L. 1997. Molecular adducts of diorganotin dichloride with N-(2-oxidoarylideneaminoacidato) diorganotin(IV) complexes. Crystal structure of [Ph2Sn(2-OC10H6CH-NCH2COO)]SnPh2Cl2., Polyhedron, 16, 573-576.
Kleinmann, D.A. 1962. Nonlinear dielectric polarization in optical media. Physical Reviews, 126, 1977-1979.
Kobayashi, T. (ed.). 1989. Nonlinear Optics of Organic and Semiconductors. Springer, Berlin.
Kohn, W. and Sham, L.J. 1965. Self-Consistent Equations Including Exchange and Correlation Effects. Physical Review, 140, A1133-A1138.
Köysal, Y. and Tanak, H. 2012. Crystal structure, spectroscopic investigations and density functional studies of 4-(4-methoxyphenethyl)-5-benzyl-2H-1,2,4-triazol- 3(4H)- one monohydrate. Spectrochimica Acta A, 93, 106-115.
Lee, C., Yang, W. and Parr, R.G. 1988. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785-789.
Liu, P.C. and Hu, W.P. 2014. The MC-DFT Approach Including the SCS-MP2 Energies to the New Minnesota-Type Functionals. Journal of Computational Chemistry, 35, 1560-1567.
Lockhart, T.P. and Manders, W.F. 1986. Structure determination by NMR spectroscopy. Dependence of 2J(119Sn,1H) on the Me-Sn-Me angle in methyltin(IV) compounds. Inorganic Chemistry, 25, 892-895.
Lockhart, T.P., Calabrese, J.C. and Davidson, F. 1987. Structural studies of diorganotin(IV) carboxylates. X-ray and NMR structures of Me2Sn(OAc)2 and a 7-coordinate tin anion, Me2Sn(OAc)3 NMe4.2CHCl3. Organometallics 6, 2479-2483.
Lodewyk, M.W., Siebert, M.R. and Tantillo, D.J. 2012. Computational prediction of 1H and 13C chemical shifts: a useful tool for natural product, mechanistic, and synthetic organic chemistry. Chemical Review 112, 1839-1862.
Majer, R., Konechnaya, O., Delso, I., Tejero, T., Attanasi, O.A., Santeusanio, S. and Merino, P. 2014. Highly diastereoselective 1,3-dipolar cycloadditions of chiral non-racemic nitrones to 1,2-diaza-1,3-dienes: an experimental and computational investigation. Organic Biomolecular Chemistry, 12, 8888-8901.
88
Matczak, P. 2015. Assessment of various density functionals for intermolecular N-Sn interactions: The test case of poly(trimethyltin cyanide). Computational and Theoretical Chemistry, 1051, 110-122.
Matczak, P. and Wojtulewski, S. 2015. Performance of Møller-Plesset second-order perturbation theory and density functional theory in predicting the interaction between stannylenes and aromatic molecules. Journal of Molecular Modeling, 21, 41.
Michele, A., Girolamo, C., Tiziana, F., Giulia, G., Claudia, P., Michelangelo, S., Alberto, S. and Lorenzo, P. 2010. Structural characterization of triorganotin(IV) complexes with sodium fusidate an DFT calculations. Journal of Organometallic Chemistry, 695, 1405-1413.
Migda, W. and Rys, B. 2004. GIAO/DFT evaluation of 13C NMR chemical shifts of selected acetals based on DFT optimized geometries. Magnetic Resonance Chemistry 42, 459-466.
Miller, D.P. and Craigh P.J. 1998. The analysis of organotin compounds from the natural environment. In: Chemistry of tin. Smith, P.J. (ed), Blackie Acad and Prof, 540- 565, London.
Minenkov, Y., Singstad, A., Occhipinti, G. and Jensen, V.R. 2012. The accuracy of DFT- optimized geometries of functional transition metal compounds: a validation study of catalysts for olefin metathesis and other reactions in the homogeneous phase. Dalton Transactions, 41, 5526-5537.
Moller, C., Plesset, M.S. 1934. Note on an Approximation Treatment for Many-Electron Systems. Physical Review, 46, 618-622.
Naseh, M., Sedaghat, T., Tarassoli, A. and Shakerzadeh, E. 2012. DFT studies of ONO Schiff bases, their anions and diorganotin(IV) complexes: Tautomerism, NBO and AIM analysis. Computational and Theoretical Chemistry, 1005, 53-57.
Naseh, M., Sedaghat, T., Tarassoli, A. and Shakerzadeh, E. 2013. DFT studies of ONO Schiff bases, their anions and diorganotin(IV) complexes: tautomerism, NBO and AIM analysis. Computational and Theoretical Chemistry, 1005, 53-57.
Nath, M., Yadav, R., Gielen, M., Dalil, H., Vos, D. and Eng, G. 1997. Synthesis, characteristic spectral studies and in vitro antimicrobial and antitumour activities of organotin(IV) complexes of Schiff bases derived from amino-acids. Applied Organometallic Chemistry, 11, 727-736.
O’Boyle, N.M., Tenderholt, A.L. and Langner, K.L. 2008. CCLIB: a library for package-independent computational chemistry algorithms. Journal of Computational Chemistry, 29, 839-845.
89
Öztaş, S.G., Şahin, E., Ancın, N., İde, S. and Tüzün, M. 2004. Structural and spectral studies of N-(3-hydroxypyridine-2-yl)-5-hydroxysalicylideneimine and its dimethyltin(IV) complex. Journal of Molecular Structure, 705, 107-112.
Öztaş¸ N.A., Yenişehirli, G., Ancın, N., Öztas, S.G., Özcan, Y. and İde, S. 2009.
Synthesis, characterization, biological activities of dimethyltin(IV) complexes of Schiff bases with ONO-type donors. Spectrochimica Acta Part A, 72, 929-935.
Peach, M.J.G., Benfield, P., Helgaker, T. and Tozer, D.J. 2008. Excitation energies in density functional theory: an evaluation and a diagnostic test. Journal of Physical Chemistry, 128, 044118.
Pearson, R.G. 1989. Absolute electronegativity and hardness: applications to organic chemistry. Journal of Organic Chemistry, 54, 1423-1430.
Pellerito, L., Prinzivalli, C., Casella, G., Fiore, T., Pelerito, O., Giuliano, M., Scopelliti, M. and Pellerito, C. 2010. Diorganotin(IV) N-acetyl-Lcysteinate complexes:
synthesis, solid state, solution phase, DFT, and biological investigations. Journal of Inorganic Biochemistry, 104, 750-758.
Percy, G.C. and Thornton, D.A. 1972. N-aryl salicylaldimine complexes: Infrared and PMR spectra of the ligands and vibrational frequencies of their metal(II) chelates. Journal of Inorganic Nuclear Chemistry, 34, 3357-3369.
Perdew, J.P, Chevary, J.A., Vosko, S.H., Jackson, K.A., Pederson, M.R., Singh, D.J.
and Fiolhais, C. 1992. Atoms, molecules, solids, and surfaces: Applications of the generalized gradient approximation for exchange and correlation. Physical Reviews B, 46, 6671-6687.
Perdew, J.P. 1986. Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Physical Review B, 33, 8822-8824.
Pettinari, C., Marchetti, F., Pettinari, R., Martini, D., Drozdov, D. and Troyanov, S.
2001. Synthesis and characterisation of tin(IV) and organotin(IV) derivatives 2-{[(2- hydroxyphenyl)imino]methyl}phenol. Inorganica Chimica Acta, 325, 103-114.
Peverati, R. and Truhlar, D.G. 2012. Screened-exchange density functionals with broad accuracy for chemistry and solidstate physics. Physical Chemistry Chemical Physics, 14, 16187-161191.
Poller, R.C. 1970. The Chemistry of Organotin Compounds, Logos Press Limited, 315, London
Pople, J. and Beveridge, D. 1970. Approximate Molecular Orbital Theory, McGraw- Hill.
90
Pople, J., Santry, D.P. and Segal, G. 1965. Approximate Self‐Consistent Molecular Orbital Theory. I. Invariant Procedures. Journal of Chemical Physics, 43, 129.
Pople, J.A., Beveridge, D. and Dobosh, P. 1967. Approximate self-consistent molecular- orbital theory. 5. Intermediate neglect of differential overlap. Journal of Chemical Physics, 47, 2026-2033.
Pople, J.A., Seeger, R. and Krishnan, R. 1977. Variational Configuration Interaction Methods and Comparison with Perturbation Theory. International Journal of Quantum Chemistry, 12, 149-163.
Pyykkö, P. 1988. Relativistic effects in structural chemistry. Chemical Reviews, 88, 563- 594.
Rablen, P.R., Pearlman, S.A. and Finkbiner, J. 1999. A comparison of density functional methods for the estimation of proton chemical shifts with chemical accuracy. Journal of Physical Chemistry A, 103, 7357-7363.
Raghavachari, K., Schlegel, H.B. and Pople, J.A. 1980. Derivative studies in configuration-interaction theory. Journal of Chemical Physics, 72, 4654-4655.
Raghavachari, K., Schlegel, H.B. and Pople, J.A. 1981. Calculation of one-electron properties using limited configuration-interaction techniques. International Journal of Quantum Chemistry, 20, 1067-1071.
Rain, J., Bally, T. and Rablen, P.R. 2009. Calculating accurate proton chemical shifts of organic molecules with density functional methods and modest basis sets.
Journal of Organic Chemistry, 74, 4017-4023.
Reyes, H. Garcia, C., Farfan, N., Santillan, R., Lacroix, P.G., Lepetit, C. and Nakatani, K. 2004. Syntheses, crystal structures, and quadratic nonlinear optical properties in four “push–pull” diorganotin derivatives. Journal of Organometallic Chemistry, 689, 2303-2310.
Rivera, J.M., Guzman, D., Rodriguez, M., Lamere, J.F., Nakatani, K., Santillan, R., Lacroix, P.G. and Farfan, N. 2006. Synthesis, characterization and nonlinear optical properties in a series of new chiral organotin(IV) Schiff base complexes.
Journal of Organometallic Chemistry, 691, 1722.
Rosenburg, D.W., Drummond, G.S. and Kappas, A. 1982. The influence of organometals on heme metabolism. In vivo and in vitro studies with organotins.
Molecular Pharmacology, 21, 150-158.
Ross, Alexander. 1965. Industrial Applications of Organotin Compounds. Annals of the New York Academy of Sciences, 125, 107-123.
Ruusuvuori, K., Kurtén, T., Ortega, I.K., Loukonen, V., Toivola, M., Kulmala, M. and Vehkamäki, H. 2011. Density-functional study of the sign preference of the
91
binding of 1-propanol to tungsten oxide seed particles. Computational and Theoretical Chemistry 966, 322-327.
Saebø, S. and Almlöf, J. 1989. Avoiding the integral storage bottleneck in LCAO calculations of electron correlation. Chemical Physics Letters, 154, 83-89.
Safinej, F., Thompson, C.D. and Khiavi, M.A. 2009. Optical and vibrational properties of 1,2-benzenedicarboxylicanhydride. Journal of Molecular Modelling, 15, 1119- 1124.
Sahu, R., Thakur, D.S. and Kashyap, P. 2012. Schiff Base: An Overview of its Medicinal Chemistry. Potential for New Drug Molecules. International Journal of Pharmaceutical Sciences and Nanotechnology, 5, 1757-1764.
Saraswat, B.S., Srivastava, G. and Mehrotra, R.C. 1977. Schiff base complexes of organotin(IV). Reactions of trialkyltin(IV) chlorides and alkoxides with N-substituted salicylideneimines. Journal of Organometallic Chemistry, 129, 155-161.
Sarotti, A.M. and Pellegrinet, S.C. 2009. A multi-standard approach for GIAO 13C NMR calculations. Journal of Organic Chemistry, 74, 7254-7260.
Sarotti, A.M. and Pellegrinet, S.C. 2012. Application of the the multistandard methodology for calculating 1H NMR chemical shifts. Journal of Organic Chemistry, 77, 6059-6065.
Saxena, A., Tandon, J.P. and Crowe, A.J. 1985. Synthesis and spectroscopic studies on organotin derivatives of biologically active Schiff bases. Polyhedron 4, 1085-1089.
Sebestík, J., Safarik, M. and Bour, P. 2012. Ferric complexes of 3-hydroxy-4-pyridinones characterized by density functional theory and Raman and UV–vis spectroscopies. Inorganic Chemistry, 51, 4473-4481.
Sedaghat, T., Naseh, M., Bruno, G., Rudbari, H.A. and Motamedi, H. 2012b. New diorganotin(IV) complexes with 3-(2-hydroxy-5-methylphenylamino)-1,3-diphenylprop-2-en-1-one: Synthesis, spectroscopic characterization, structural studies and antibacterial activity. Journal of Molecular Structure, 1026, 44-50.
Sedaghat, T., Naseh, M., Khavasi, H.R. and Motamedi, H. 2012a. Synthesis, spectroscopic investigations, crystal structures and antibacterial activity of 3-(3-hydroxypyridin-2-ylamino)-1-phenylbut-2-en-1-one and its diorganotin(IV) complexes. Polyhedron, 33, 435-440.
Segal, G. and Pople, J. 1966. Approximate self-consistent molecular orbital theory. 3.
CNDO results for AB2 and AB3 systems. Journal of Chemical Physics, 44, 3289-3296.
92
Shah, F.A., Sabir, S., Fatima, K., Ali, S., Qadri, I. and Rizzoli, C. 2015. Organotin(IV) based anti-HCV drugs: synthesis, characterization and biochemical activity. 44, 10467-10478.
Sherrill, C.D. and Schaefer, H.F. 1999. The Configuration Interaction Method:
Advances in Highly Correlated Approaches, Advances in Quantum Chemistry, Lowdin, P.O. (editör), Academic Press, 143-269, New York.
Shujah, S., Rehman, Z., Muhammad, N., Ali, S., Khalid, N. and Tahir, M.N. 2011. New dimeric and supramolecular organotin(IV) complexes with a tridentate schiff base as potential biocidal agents. Journal of Organometallic Chemistry, 696, 2772-2781.
Smith, F.E., Khoo, L.E., Goh, N.K., Hynes, R.C. and Eng, G. 1996. The synthesis, and molecular and crystal structure of diphenyl(2-oxidonaphthylmethyl-iminoacetato)tin(lV). Canadian. Journal of Chemistry, 74, 2041-2047.
Smith, P.J. 1978. Toxicological Data on Organotin Compounds. International Tin Research Institute, Publication No. 538, 1, London.
Stephens P.J., Devlin F.J., Chabalowski C.F. and Frisch M.J. 1994. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. Journal of Physical Chemistry, 98, 11623-11627.
Stewart, J.P.P. 2007. Optimization of parameters for semiempirical methods. V.
Modification of NDDO approximations and application to 70 elements. Journal of Molecular Modelling, 13, 1173-1213.
Szabo, A. and Ostlund, N.S. 1989. Modern Quantum Chemistry, McGraw-Hill Publishing Co., 480, New York.
Tao, J.M., Perdew, J.P., Staroverov, V.N. and Scuseria, G.E. 2003. Climbing the density functional ladder: Nonempirical meta-generalized gradient approximation designed for molecules and solids. Physical Review Letters, 91, 146401.
Tarafder, M.T.H., Chew, K.B., Crouse, K., Ali, A.M., Yamin, B.M. and Fun, H.K.
2002. Synthesis and characterization of Cu(II), Ni(II) and Zn(II) metal complexes of bidentate NS isomeric Schiff bases derived from S-methyldithiocarbazate (SMDTC): bioactivity of the bidentate NS isomeric Schiff bases, some of their Cu(II), Ni(II) and Zn(II) complexes and the X-ray structure of the bis[S-methyl- β-N-(2-furyl methyl) methylenedithiocarbazato]
zinc(II) complex. Polyhedron, 21, 2683-2690.
Tarı, G., Gümüs, S. and Agar, E. 2015. Crystal structure, spectroscopic studies and quantum mechanical calculations of 2-[((3-iodo-4-methyl)phenylimino)methyl]-5-nitrothiophene. Spectrochimica Acta A, 141, 119-127.
93
Tian, L., Qian, B., Sun, Y., Zheng, X., Yang, M., Li, H. and Liu, X. 2005. Synthesis, structural characterization and cytotoxic activity of diorganotin(IV) complexes of N-(5-halosalicylidene)-α-amino acid. Applied Organometallic Chemistry, 19, 980-987.
Tian, T., Shang, Z., Zheng, X., Sun, Y., Yul, Y., Qian, B. and Liu, X. 2006. Synthesis, characterization and biological activity of diphenyltin(IV) complexes of N-(3,5-dibromosalicylidene)-α-amino acid and their diphenyltin dichloride adducts.
Applied Organometallic Chemistry, 20, 74-80.
Williams, D.J (ed.). 1985. Nonlinear Optical Properties of Organic and Polymer Materials. American Chemical Society, 244, Washington, DC
Wrackmeyer, B. 1985. Tin-119 NMR Parameters. Annual Reports on NMR Spectroscopy, 16, 73-186.
Yanai, T., Tew, D. and Handy, N. 2004. A new hybrid exchangecorrelation functional using the Coulomb-attenuating method (CAM-B3LYP). Chemical Physics Letters, 393, 51-57.
Yenişehirli, G., Öztaş, N.A., Şahin, E., Çelebier, M., Ancın, N. and Öztaş, S.G. 2010.
Synthesis, Characterization, and In Vitro Antimicrobial Activities of Organotin(IV) Complexes of Schiff Bases with ONO-type Donor Atoms.
Heteroatom Chemistry, 21, 373-385.
Zhang, G. and Musgrave, C.B. 2007. Comparison of DFT methods for molecular orbital eigenvalue calculations. Journal Physical Chemistry A, 111, 1554-1561.
Zhao, L., Huang, F., Lu, G., Wang, Z.X. and Schleyer, P.R. 2012. Why the mechanisms of digermyne and distannyne reactions with H2 differ so greatly. Journal of American Chemical Society, 134, 8856-8868.
94 EKLER
EK 1 H2L1’in FT-IR Spektrumu