4-siyano Grubu İçeren Schiff Bazı Bileşiklerin Sentezi Karakterizasyonu ve Teorik Hesaplamalar

Yıl 2016, Cilt: 16 Sayı: 3, 561 - 568, 31.12.2016

Engin Yılmaz

Öz

Bu çalışmada üç adet schiff bazı bileşik sentezlenmiştir. Sentezlenen bileşiklerin karakterizasyonları FT-IR, NMR ve Uv-görünür bölge spektroskopisi yöntemleri ile yapılmıştır. Sentezlenen bileşiklerin aseton, 1,4-dioksan ve dimetilsülfoksit çözücülerinde UV-görünür bölge içerisindeki davranışları incelendi. Çalışmanın son aşamasında ise bileşiklere ait teorik hesaplamalar Gaussian 09 yazılımı ile yapılmıştır.

Anahtar Kelimeler

Schiff Bazı, 4-siyano, Gaussian 09, Çözücü Etkisi

Kaynakça

• Abdel-Kader, N. S., El-Ansary A. L., El-Tayeb T. A. and Elnagdi M. M. F. (2016). "Synthesis and characterization of Schiff base complexes derived from cephradine: Fluorescence, photostability and photobiological applications." Journal of Photochemistry and Photobiology A: Chemistry 321: 223-237.
• Bellamy, L. J. (1975). The IR Spectra of complex Molecules. NewYork, John Wiley and Sons
• Chattaraj, P. K. and Giri S. (2007). "Stability, reactivity, and aromaticity of compounds of a multivalent superatom." Journal of Physical Chemistry A 111(43): 11116-11121.
• Çay, S., Köse M., Tümer F., Gölcü A. and Tümer M. (2015). "SOD activity and DNA binding properties of a new symmetric porphyrin Schiff base ligand and its metal complexes." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 151: 821-838.
• de Toledo, T. A., da Costa R. C., da Silva L. E., Teixeira A. M. R., Lima V. N., Sena Jr D. M., Coutinho H. D. M., Freire P. T. C. and Pizani P. S. (2016). "Thermal and biological properties of the Schiff base N,N′-bis(salicylidene)-1,2-phenylenediamine, a potential adjuvant to antibiotic therapy." Journal of Molecular Structure 1115: 105-108. Gandhimathi, S., Balakrishnan C., Venkataraman R. and Neelakantan M. A. (2016). "Crystal structure, solvatochromism and estimation of ground and excited state dipole moments of an allyl arm containing Schiff base: Experimental and theoretical calculations." Journal of Molecular Liquids 219: 239-250.
• Gao, Z., M. Lv, Li Q. and Xu H. (2015). "Synthesis of heterocycle-attached methylidenebenzenesulfonohydrazones as antifungal agents." Bioorganic & Medicinal Chemistry Letters 25(22): 5092-5096.
• García-López, M. C., Muñoz-Flores B. M., Jiménez-Pérez V. M., Moggio I., Arias E., Chan-Navarro R. and Santillan R. (2014). "Synthesis and photophysical characterization of organotin compounds derived from Schiff bases for organic light emitting diodes." Dyes and Pigments 106: 188-196.
• Geerlings, P., De Proft F. and Langenaeker W. (2003). "Conceptual density functional theory." Chemical Reviews 103(5): 1793-1873.
• Ghasemian, M., Kakanejadifard A., Azarbani F., Zabardasti A. and Kakanejadifard S. (2014). "The triazine-based azo–azomethine dyes; spectroscopy, solvatochromism and biological properties of 2,2′-((2,2′-(6-methoxy-1,3,5-triazine-2,4-diyl) bis(oxy)bis(2,1-phenylene))bis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene))bis(4-phenyldiazenyl)phenol." Journal of Molecular Liquids 195: 35-39.
• Ghosh, P., Kumar N., Mukhopadhyay S. K. and Banerjee P. (2016). "Sensitive and fluorescent Schiff base chemosensor for pico molar level fluoride detection: In vitro study and mimic of logic gate function." Sensors and Actuators B: Chemical 224: 899-906.
• M.J.F. R. A. Gaussian 09, G. W. T., H. B. Schlegel, G.E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT , 2009. Mahlooji, N., Behzad M., Amiri Rudbari H., Bruno G. and Ghanbari B. (2016). "Unique examples of copper(II)/sodium(I) and nickel(II)/sodium(I) Schiff base complexes with bridging bis-bidentate Salen type ligand: Synthesis, crystal structures and antibacterial studies." Inorganica Chimica Acta 445: 124-128.
• Panda, U., Roy S., Mallick D., Dalapati P., Biswas S., Manik N. B., Bhattacharyya A. and Sinha C. (2016). "Aggregation induced emission enhancement of pyrene-appended Schiff base luminophore and its photovoltaic effect." Journal of Luminescence 175: 44-49.
• Parr, R. G. and Pearson R. G. (1983). "Absolute Hardness - Companion Parameter to Absolute Electronegativity." Journal of the American Chemical Society 105(26): 7512-7516.
• Parr, R. G., Von Szentpaly L. and Liu S. B. (1999). "Electrophilicity index." Journal of the American Chemical Society 121(9): 1922-1924.
• Pearson, R. G. (1989). "Absolute Electronegativity and Hardness - Applications to Organic-Chemistry." Journal of Organic Chemistry 54(6): 1423-1430.
• Pradeep Kumar, M., Tejaswi S., Rambabu A., Kalalbandi V. K. A. and Shivaraj (2015). "Synthesis, crystal structure, DNA binding and cleavage studies of copper(II) complexes with isoxazole Schiff bases." Polyhedron 102: 111-120.
• Shakir, M., Abbasi A., Faraz M. and Sherwani A. (2015). "Synthesis, characterization and cytotoxicity of rare earth metal ion complexes of N,N′-bis-(2-thiophenecarboxaldimine)-3,3′-diaminobenzidene, Schiff base ligand." Journal of Molecular Structure 1102: 108-116.
• Sıdır, İ., Sıdır Y. G., Berber H. and Türkoğlu G. (2016). "Specific and non-specific interaction effect on the solvatochromism of some symmetric (2-hydroxybenzilydeamino)phenoxy Schiff base derivatives." Journal of Molecular Liquids 215: 691-703.
• Taghi Sharbati, M., Soltani Rad M. N., Behrouz S., Gharavi A. and Emami F. (2011). "Near infrared organic light-emitting diodes based on acceptor–donor–acceptor (ADA) using novel conjugated isatin Schiff bases." Journal of Luminescence 131(4): 553-558.
• Wan, L., Shu Q., Zhu J., Jin S., Chen N. Li, X. and Chen S. (2016). "A new multifunctional Schiff-based chemosensor for mask-free fluorimetric and colorimetric sensing of F− and CN−." Talanta 152: 39-44.
• Wang, K., Ma L., Liu G., Cao D., Guan R. and Liu Z. (2016). "Two fluorescence turn-on coumarin Schiff's base chemosensors for cyanide anions." Dyes and Pigments 126: 104-109.
• Xu, Z.-Q., Mao X.-J., Jia L., Xu J., Zhu T.-F., Cai H.-X., Bie H.-Y., Chen R.-H. and Ma T.-l. (2015). "Synthesis, characterization and anticancer activities of two lanthanide(III) complexes with a nicotinohydrazone ligand." Journal of Molecular Structure 1102: 86-90.