N<strong>’</strong>-(2,5 Dihidroksibenziliden)-2-Hidroksi-3-Metilbenzohidrazid Bileşiğinin Tautomer Yapısının Teorik Olarak İncelenmesi

Yıl 2018, Cilt: 22 Sayı: Özel, 257 - 262, 05.10.2018

Tuncay Karakurt

Öz

Bu çalışmada, bir Schiff bazı olan N’-(2,5 dihidroksibenziliden)-2-hidroksi-3-metilbenzohidrazid molekülünün fenol-imin ve keto–amin gibi iki tautomer formu üzerinde gaz ve periyodik sınır şartlarında katı fazında teorik hesaplamalar yapılmıştır. Bu iki toutomer yapı için teorik olarak 6-31G(d) temel setli Becke-3- Lee-Yang-Parr (B3LYP) metodu kullanarak gaz fazında molekülün bazı geometriksel parametreleri ve frontier moleküler orbital değerleri (FMO), gaussian 09 programı ile incelenmiştir. Katı fazında ise her iki formun birim hücre örgü enerjileri, periyodik sınır şartları (PBC) altında Quantum-Espresso paket programı ile hesaplanmıştır. Teorik tüm çalışmalar, iki tautomer yapı üzerinde yapılmıştır. Yapılan tüm hesaplamalarda bileşiğin, hem gaz hem de katı fazında fenol-imin formunun daha kararlı olduğu görülmüştür.

Anahtar Kelimeler

Gaussian 09W, Fenol–imin; Keto–amin; Quantum-Espresso

Kaynakça

• [1] O’neil, M. J., Smith, A. & Heckelman, P. The Merck Index, 13th edn. Merck & Co. Inc., Whitehouse Station, NJ, 6596, 2001.
• [2] Ayhan‐Kılcıgil, G., Kus, C., Özdamar, E. D., can‐eke, B. & Iscan, M., Synthesis and antioxidant capacities of some new benzimidazole derivatives. Archiv der Pharmazie, 340, 607-611, 2007.
• [3] Kus, C., Ayhan-Kilcigil, G. & Eke, B. C. Synthesis and antioxidant properties of some novel benzimidazole derivatives on lipid peroxidation in the rat liver. Archives of Pharmacal Research, 27, 156, 2004.
• [4] Karakurt, T., Cukurovali, A., Subasi, N. T. & Kani, I., Molecular structure and computational studies on 2-((2-(4-(3-(2, 5-dimethylphenyl)-3-methylcyclobutyl) thiazol-2-yl) hydrazono) methyl) phenol monomer and dimer by DFT calculations. Journal of Molecular Structure, 1125, 433-442, 2016.
• [5] Macho, V., Králik, M., Hudec, J. & Cingelova, J., One stage preparation of Schiff’s bases from nitroarenes, aldehydes and carbon monoxide at presence of water. Journal of Molecular Catalysis A: Chemical, 209, 69-73, 2004.
• [6] Issaadi, S., Douadi, T., Zouaoui, A., Chafaa, S., Khan, M. & Bouet, G., Novel thiophene symmetrical Schiff base compounds as corrosion inhibitor for mild steel in acidic media. Corrosion Science, 53, 1484-1488, 2011.
• [7] Reddy, K. H., Reddy, P. S. & Babu, P.R., Nuclease activity of mixed ligand complexes of copper (II) with heteroaromatic derivatives and picoline. Transition Metal Chemistry, 25, 505-510, 2000.
• [8] Jarahpour, A., Motamedifar, M., Pakshir, K., Hadi, N. & Zarei, M., Synthesis of novel azo Schiff bases and their antibacterial and antifungal activities. Molecules, 10, 815-824, 2004.
• [9] Jalali-Heravi, M., Khandar, A. & Sheikshoaie, I., A theoretical investigation of the structure, electronic properties and second-order nonlinearity of some azo Schiff base ligands and their monoanions. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 55, 2537-2544, 1999.
• [10] Ünver, H., Karakas, A. & Elmali, A., Nonlinear optical properties, spectroscopic studies and structure of 2-hydroxy-3-methoxy-N-(2-chloro-benzyl)-benzaldehyde-imine. Journal of Molecular Structure, 702, 49-54, 2004.
• [11] Han, Y.-Y., Li, Y.-H. & Zhao, Q.-R., N′-(2,5 Dihydroxybenzylidene)-2-hydroxy-3-methylbenzohydrazide. Acta Crystallographica Section E: Structure Reports Online, 66, o1091-o1091, 2010.
• [12] Foresman, J.B. And Frisch, A., Exploring Chemistry with Electronic Structure Methods, 2nd ed. (Gaussian Inc.,Pittsburgh, PA, ), 1996.
• [13] Becke, A. D., Density‐functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics, 98, 5648-5652, 1993.
• [14] Lee, C., Yang, W. & Parr, R. G., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical review B, 37, 785, 1988.
• [15] Frisch, M., Trucks, G., Schlegel, H., Scuseria, G., Robb, M., Cheeseman, J., Scalmani, G., Barone, V., Mennucci, B. & Petersson, G., Gaussian 09, revision D. 01. Gaussian, Inc., Wallingford CT., 2009.
• [16] Giannozzi, P., Baroni, S., Bonini, N., Calandra, M., Car, R., Cavazzoni, C., Ceresoli, D., Chiarotti, G. L., Cococcioni, M. & Dabo, I., Quantum Espresso: a modular and open-source software project for quantum simulations of materials. Journal of Physics: Condensed Matter, 21, 395502, 2009.
• [17] Dennington, R., Keith, T. & Millam, J., GaussView, version 5. 2009.
• [18] Hohenberg, P. & Kohn, W., Inhomogeneous electron gas. Physical Review, 136, B864, 1964.
• [19] Kohn W., and Sham L.J., Physical Review, 140, A1133, 1965.
• [20] Perdew J.P. and Zunger, A., Physical Review B: Condensed Matter, 23, 5048, 1981.
• [21] Karakurt, T., Cukurovali, A., Subasi, N. T., Onaran, A., Ece, A., Eker, S. & Kani, I. Experimental and theoretical studies on tautomeric structures of a newly synthesized 2, 2’(hydrazine-1, 2-diylidenebis (propan-1-yl-1-ylidene)) diphenol. Chemical Physics Letters, 693, 132, 2018.
• [22] Atkins, P., Paula J. Atkins' physical chemistry. New York: WH Freeman and Company, 2006.
• [23] Fukui K., Role of frontier orbitals in chemical reactions. Science, 218, 747-754, 1982.
• [24] Alaghaz, A.-N.M., Zayed, M.E., Alharbi, S.A., Ammar, R.A., Elhenawy, A. Synthesis, characterization, biological activity, molecular modeling and docking studies of complexes 4-(4-hydroxy)-3-(2-pyrazine-2-carbonyl) hydrazonomethylphenyl-diazen-yl-benzenesulfonamide with manganese (II), cobalt (II), nickel (II), zinc (II) and cadmium (II). J. Mol. Struct. 1084, 352-367, 2015.
• [25] Er, M., Ergüven B., Tahtacı H., Onaran A., Karakurt T., Ece A. Synthesis, characterization, preliminary SAR and molecular docking study of some novel substituted imidazo[2,1-b][1,3,4] thiadiazole derivatives as antifungal agents. Med. Chem. Res. 26, 615-630, 2017.