In Silico İnvestigation Of The Complexation Properties of S,S'-bis(2-pyridinyl)-2,2'-dithiosalicylthioat Compound with Iron (III) Ion

Yıl 2024, , 1087 - 1093, 01.10.2024

Ümit Çalışır , Baki Çiçek

https://doi.org/10.35414/akufemubid.1472359

Öz

S,S’-bis(2-pyridinyl)-2,2’-dithiosalicylthioat compound is one of the sulfur compounds containing disulfide bonds. Additionally, there are thioester groups in the compound. It is reported in the literature that S,S’-bis(2-pyridinyl)-2,2’-dithiosalicylthioat compound has a high affinity for Fe3+ ion (Ext.%: 98.02) according to the extraction constants and results determined by liquid-liquid ion pair extraction. Within the scope of this study, the charge distribution, bond lengths, electrostatic distribution maps, energy parameters and molecular orbitals of this compound and the iron (III) complex it forms at high levels were calculated with the HyperChem program. The most stable structures of the compound and the iron (III) complex were determined and the energy parameters of the formation of the complex were determined. In the light of the data obtained, it was determined that the iron (III) complex formed had lower energy, lower ionization potential and lower LUMO-HOMO electron gap.

Anahtar Kelimeler

Computational chemistry; Thioester, Disulfide bond, Iron (III) complex, HyperChem, HOMO-LUMO.

S,S'-bis(2-piridinil)-2,2'-ditiyosalisiltiyoat Bileşiğinin Demir (III) İyonu ile Kompleksleşme Özelliklerinin in Silico İncelenmesi

Öz

S,S’-bis(2-piridinil)-2,2’-ditiyosalisiltiyoat bileşiği disülfit bağı içeren kükürtlü bileşiklerdendir. Ayrıca bileşikte tiyoester grupları mevcuttur. S,S’-bis(2-piridinil)-2,2’-ditiyosalisiltiyoat bileşiğinin sıvı-sıvı iyon çiftleri ekstraksiyonu ile belirlenen ekstraksiyon sabitleri ve sonuçlarına göre Fe3+ iyonuna yüksek afinite gösterdiği (% Ext.: 98.02)literatürde verilmektedir. Bu bileşiğin ve yüksek oranda oluşturduğu demir (III) kompleksinin, bu çalışma kapsamında yük dağılımı, bağ uzunlukları, elektrostatik dağılım haritaları, enerji parametreleri ve moleküler orbitalleri HyperChem programı ile hesaplanmıştır. Bileşiğin ve demir (III) kompleksinin en kararlı yapılarının belirlenmesi oluşan kompleksin oluşumuna dair enerji parametrelerinin belirlenmesi gerçekleştirilmiştir. Elde edilen veriler ışığında oluşan demir (III) kompleksinin daha düşük enerjiye sahip olduğu, iyonlaşma potansiyelinin daha düşük olduğu ve LUMO-HOMO elektron boşluğunun daha düşük olduğu tespit edilmiştir.

Anahtar Kelimeler

Hesapsal kimya, Tiyoester, Disülfit bağı, Demir (III) kompleksi, Hyperchem, HOMO-LUMO.

Kaynakça

• Calisir, U. ve Çakır, F., (2022). Investigation of some theoretical (computational) properties of 2-amino-6-methylpyridine and 2-amino-4,6-dimethylpyrimidine compounds using hyperchem software. Turkish Journal of Applied Sciences and Technology, 3(1), 13–24. https://doi.org/10.5281/zenodo.7236656
• Calisir, U. ve Çiçek, B., (2017). Comparison of classic and microwave-assisted synthesis of benzo-thio crown ethers, and investigation of their ion pair extractions. Journal of Molecular Structure, 1148, 505–511. https://doi.org/10.1016/j.molstruc.2017.07.081
• Çalışır, Ü. ve Çiçek, B., (2022). Synthesis, characterization and determination of some theoretical properties of ethyl 2-((4,6-dimethylpyrimidin-2-yl)amino)acetate. III. International Siirt Conference On Scientific Research. Siirt, Türkiye, 686–696.
• Çalışır, Ü., (2021). S,S’-Dipyridin-2-yl 2,2’-disulfanedidibenzenecarbotioate: Microwave assisted synthesis, characterization, and investigation of metal extraction properties. International Siirt Scientific Research Congress. Siirt, Türkiye, 539-546.
• Çalışır, Ü., (2022). Synthesis and characterization of some benzothioate derivatives and investigation of extractions with Cr3+, Co2+, Cu2+, Mn2+, Fe3+, Zn2+ ions. Balıkesir Universitesi Fen Bilimleri Enstitüsü Dergisi, 24(1), 212–221. https://doi.org/10.25092/baunfbed. 937720
• Çalışır, Ü., Camadan, Y., Çiçek, B., Akkemik, E., Eyüpoğlu, V., ve Adem, Ş., (2022). Synthesis, characterizations of aryl-substituted dithiodibenzothioate derivatives, and investigating their anti-Alzheimer’s properties. Journal of Biomolecular Structure and Dynamics, 41(5), 1828-1845. https://doi.org/10.1080/07391102.2021.2024884
• Çalışır, Ü., ve Çiçek, B., (2023). Bazı yeni N - sübstitüe amino asit esterlerinin yapısal özelliklerinin in silico ile araştırılması. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 25(2), 748–760. https://doi.org/10.25092/baunfbed.1310449
• Çiçek, B., ve Çalışır, Ü., (2016). The investigation of complexation properties and hard-soft acid-base relationship between thiacrown ethers and metal ions. Letters in Organic Chemistry, 13(8), 572–577. https://doi.org/10.2174/1570178613666160906105300
• Çiçek, B., ve Yıldız, A., (2011). The investigation of complexation properties and hard-soft acid-base relationship between thiacrown ethers and metal ions. Molecules, 16, 8670-8683. https://doi.org/10.3390/molecules16108670
• Eshghi, H., Seyedi, S. M., ve Sandarooss, R., (2007). Synthesis of novel disulfide-bridged dilactam crown ethers. Chinese Chemical Letters, 18(12), 1439–1442. https://doi.org/10.1016/j.cclet.2007.10.027
• Fleming, I., (2010). Molecular orbitals and organic chemical reactions. John Wiley & Sons, Ltd, 69–125. Gilbert, H. F., (2013). Encyclopedia of Biological Chemistry. Lennarz, W. J. ve Lane, M. D. (editörler.), 2. Baskı, Academic Press, 664–667.
• Howard, A., McIver, J., ve Collins, J., (1994). HyperChem Computational Chemistry (Howard, A., McIver, J. ve Collins, J. (editörler.). Hypercube Inc., Waterloo.
• Hutchison, A., Atwood, D., ve Santilliann-Jiminez, Q.E., (2008). The removal of mercury from water by open chain ligands containing multiple sulfurs. Journal of Hazardous Materials, 156(1–3), 458–465. https://doi.org/10.1016/j.jhazmat.2007.12.042
• Fleming, I., (2010). Molecular orbitals and organic chemical reactions. John Wiley & Sons, Ltd, 1–67. Kaya, S., Tüzün, B., Kaya, C., & Obot, I.B. (2016). Determination of corrosion inhibition effects of amino acids: Quantum chemical and molecular dynamic simulation study. Journal of the Taiwan Institute of Chemical Engineers, 58,528–535. https://doi.org/10.1016/j.jtice.2015.06.009
• Klopman, G., (1968). Chemical reactivity and the concept of charge- and frontier-controlled reactions. Journal of the American Chemical Society, 90(2), 223–234. https://doi.org/10.1021/ja01004a002
• Koopmans, T., (1934). Über die zuordnung von wellenfunktionen und eigenwerten zu den einzelnen elektronen eines atoms. Physica, 1(1–6), 104–113. https://doi.org/10.1016/S0031-8914(34)90011-2
• Kumer, A., Sarker, M. N., ve Paul, S., (2019). The theoretical investigation of HOMO, LUMO, thermophysical properties and QSAR study of some aromatic carboxylic acids using HyperChem programming. International Journal of Chemistry and Technology, 3(1), 26–37. https://doi.org/10.32571/ijct.478179
• Pedersen, C.J., (1991). Macrocyclic polyether sulfides. Journal of Organic Chemistry, 36(2), 254–257. https://doi.org/10.1021/jo00801a003
• Salem, L., (1968a). Intermolecular orbital theory of the interaction between conjugated systems. I. General theory. Journal of the American Chemical Society, 90(3), 543–552. https://doi.org/10.1021/ja01005a001
• Salem, L., (1968b). Intermolecular orbital theory of the interaction between conjugated systems. II. Thermal and photochemical cycloadditions. Journal of the American Chemical Society, 90(3), 553–566. https://doi.org/10.1021/ja01005a002
• Stewart, J.J.P., (1990). Reviews in computational chemistry. Lipkovitz, K. ve Boyd, D.B. (editörler), John Wiley & Sons,Inc. 45–81. Stewart, R.F., (1970). Small Gaussian expansions of Slater‐type orbitals. The Journal of Chemical Physics, 52(1), 431–438. https://doi.org/10.1063/1.1672702