Structural Characterization and Spectroscopic Studies of (E)-2,4-di-tert-butyl-6-(((4-phenoxyphenyl)imino)methyl)phenol Compound

Year 2025, Volume: 15 Issue: 1, 159 - 171, 01.03.2025

Enis Güzel , Mustafa Macit , Didem Aytaçoğlu , Metin Yavuz

https://doi.org/10.21597/jist.1528674

Abstract

Spectroscopic studies were carried out to determine the structural properties of the Schiff base C27H31NO2 compound. The studies carried out within this scope include X-ray diffraction, IR, Uv-Vis, 13C-NMR and 1H-NMR studies. The methods used in this study are the most effective methods used in determining structural characterization. It was determined that the compound whose characterization was completed was shaped in the enol-imine form. According to X-ray analysis, there are two molecules per unit cell. It was observed that there is an angle between the planes between the benzene rings of the investigated compound. In this context, it was determined that the structure was not planar. It is accepted in the literature that non-planar Schiff-based compounds mainly exhibit thermochromic properties. The interaction values of the atoms in the formation of the synthesized compound are important in terms of recognizing the compound structure and determining the dominant interaction pairs. In this context, the interaction percentages of the atoms in the compound were determined by the Hirshfeld surface analysis method. In addition, the molecular surface morphology was determined by using this program.

Keywords

Crystallography, IR, NMR, Hirshfeld surface analysis

Project Number

Bulunmamaktadır.

(E)-2,4-di-tert-bütil-6-(((4-fenoksifenil)imino)metil)fenol Bileşiğinin Yapısal Karakterizasyonu ve Spektroskopik Çalışmaları

Abstract

Schiff bazlı C27H31NO2 bileşiğinin yapısal özelliklerinin belirlenmesi için spektroskopik çalışmalar yapılmıştır. Bu kapsamda yapılan çalışmalar; X-ışını çalışması, IR çalışması, Uv-Vis çalışması, 13C-NMR çalışması ve 1H-NMR çalışmasını içermektedir. Bu çalışmada kullanılan yöntemler, yapısal karakterizasyonun belirlenmesinde kullanılan en etkili yöntemlerdir. Karakterizasyonu tamamlanan bileşiğin enol-imin formunda şekillendiği belirlenmiştir. X-ışını analizine göre birim hücre başına iki molekül düşmektedir. İncelenen bileşiğin benzen halkaları arasındaki düzlemler arasında bir açı olduğu gözlemlenmiştir. Bu bağlamda yapının düzlemsel olmadığı belirlenmiştir. Düzlemsel olmayan Schiff bazlı bileşiklerin ağırlıklı olarak termokromik özellik gösterdiği literatür verileri doğrultusunda kabul edilen bir durumdur. Sentezlenen bileşiğin oluşumunda yer alan atomların birbirleri ile olan etkileşim değerleri, bileşik yapısını tanımak ve baskın olan etkileşim çiftlerini belirlemek açısından önemlidir. Bu kapsamda bileşikte yer alan atomların etkileşim yüzdeleri Hirshfeld yüzey analizi yöntemi ile belirlenmiştir. Ek olarak, moleküler yüzey morfolojiside bu programdan yararlanılarak belirlenmiştir.

Keywords

Kristalografi, IR, NMR, Hisrhfeld Yüzey Analizi

Project Number

Bulunmamaktadır.

References

• Abdalhadi, S.M., Al-Baitai, A.Y., and Al-Zubaidi, H.A. (2021). Synthesis and Characterization of 2,3-Diaminomaleonitrile Derivatives by One-Pot Schiff Base Reaction and Their Application in Dye Synthesized Solar Cells. Indonesian Journal of Chemistry, 21(2): p. 443-451.
• Abdellah, I.M., Yildirim, E., and El-Shafei, A. (2021). Low-cost novel X-shaped hole transport materials for efficient perovskite solar cells: Molecular modelling of the core and schiff base effects on photovoltaic and photophysical properties. Materials Chemistry and Physics, 296.
• Akbari, Z., Montazerozohori, M., Bruno, G., Moulaee, K., and Neri, G. (2022). Development of a novel electrochemical nitrite sensor based on Zn‐Schiff base complexes. Applied Organometallic Chemistry, 36(4), e6610.
• Allah, A. E. M. A., Temel, E., Guerrab, W., Nchioua, I., Mague, J. T., Talbaoui, A., ... & Ramli, Y. (2024). 3-Allyl-2-(allylthio)-5, 5-diphenyl-3, 5-dihydro-4H-imidazol-4-one: Synthesis, spectroscopic characterization, crystal structure, computational investigations, antibacterial activity and ADMET studies. Journal of Molecular Structure, 1312, 138572.
• Amirthaganesan, K., Vadivel, T., Dhamodaran, M., and Chandraboss, V. L. (2022). In vitro antifungal studies of ruthenium (III) complex derived from chitosan Schiff bases. Materials Today: Proceedings, 60, 1716-1720.
• Bei, Y., Ma, Y., Song, F., Kou, Z., Hu, L., Bo, C., ... and Zhou, Y. (2022). Recent progress of biomass based self‐healing polymers. Journal of Applied Polymer Science, 139(16), 51977.
• Çoruh, U, Ustabas, R, Yılmaz, I, Yavuz, M. (2003). 4,5-Dicyano-1,2bis (2- dimethylaminoethylsulfanyl) benzene. Acta Crystallographica, E59: 8.
• Demircioğlu, Z, Ersanli, C. C, Kaya, Kantar, G, Sasmaz, S. (2019). Spectroscopic, Hirshfeld Surface, X-ray Diffraction Methodologies and local & Global Chemical Activity Calculations of 5-(2-methoxy-4-(prop-1-en-1-yl) phenoxy) pyrazine-2,3-dicarbonitrile, Journol of Molecular Structure, 25-37.
• Ersanli, C. C., Kantar, G. K., & Şaşmaz, S. (2017). Crystallographic, spectroscopic (FTIR and NMR) and quantum computational calculation studies on bis (2-methoxy-4-((E)-prop-1-enyl) phenyl) oxalate. Journal of Molecular Structure, 1143, 318-327.
• Farrugia, L.J. (2012). WinGX and ORTEP for Windows: an Update, Journal of Applied Crystallography, 45, 849-854.
• Gumus, S., Guner, H., Meral, S., & Agar, A. A. (2024). Experimental and theoretical comparison of the vibrational and NMR spectra of novel 6-6’-(1E-1’E)-(Propane-1, 3Diylbis (Azanylyidene)) Bis (Phenylmethylylidene)) Bis (3-Octyloxy) Phenol), NBO and molecular docking studies. Journal of Molecular Structure, 1299, 136949.
• Güzel, E., Macit, M., Ergüzeloğlu, E., & Yavuz, M. (2023). 3, 5-Di-Tert-Bütil-2-Hidroksibenzaldehit Bileşiğinin Kimyasal Aktivite ve Spektroskopik Çalışmaları. Journal of the Institute of Science and Technology, 13(1), 285-297.
• Ibrahim, S. M., Saeed, A. M., Abd Elmoneam, W. R., and Mostafa, M. A. (2023). Synthesis and characterization of new Schiff base bearing bis (pyrano [3, 2-c] quinolinone): Efficient cationic dye adsorption from aqueous solution. Journal of Molecular Structure, 1284, 135364.
• Jain, S., Rana, M., Sultana, R., Mehandi, R., and Rahisuddin. (2023). Schiff base metal complexes as antimicrobial and anticancer agents. Polycyclic Aromatic Compounds, 43(7), 6351-6406.
• Joseyphus, R. S., Reshma, R., Arish, D., and Elumalai, V. (2022). Antimicrobial, photocatalytic action and molecular docking studies of imidazole-based Schiff base complexes. Results in Chemistry, 4, 100583.
• Kalecik, S., Güzel, E., Doğan, O. E., Ağar, E., ve Yavuz, M. (2022). (E)-4-bromo-5-floro-2-(((4-(fenilamino) fenil) imino) metil) fenol Bileşiğinin Kimyasal Aktivite ve Spektroskopik Çalışmaları. Karadeniz Fen Bilimleri Dergisi, 12(2), 821-840.
• Kaya, S., Erkan, S., and Karakaş, D. (2021). Computational investigation of molecular structures, spectroscopic properties and antitumor-antibacterial activities of some Schiff bases. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 244, 118829.
• Kılıç Cıkla, I, Güveli, Ş.¸ Yavuz, M, Bal-Demirci, T, Ülküseven, B. (2016). 5-Methyl-2-hydroxy-acetophenone-thiosemicarbazone and its nickel(II) Complex: Crystallographic, spectroscopic (IR,NMR and IV) and DFT studies. Polyhedron, 105: 104-114.
• Maia, D. O., Santos, V. F., Barbosa, C. R., Fróes, Y. N., Muniz, D. F., Santos, A. L., ... and Teixeira, C. S. (2022). Nickel (II) chloride Schiff base complex: Synthesis, characterization, toxicity, antibacterial and leishmanicidal activity. Chemico-Biological Interactions, 351, 109714.
• Sheldrick, G. M. (2015). SHELXT–Integrated space-group and crystal-structure determination. Acta Crystallographica Section A: Foundations and Advances, 71(1), 3-8.
• Sheldrick, G. M. (2015). Crystal structure refinement with SHELXL. Acta Crystallographica Section C: Structural Chemistry, 71(1), 3-8.
• Suhta, A., Meral, S., Alaman Ağar, A., Sütay, B., Vazquez Lopez, E. M., & Çoruh, U. (2024). Synthesis and characterization of tetradentate benzophenone derivative Schiff base and properties in different lyotropic media. Molecular Crystals and Liquid Crystals, 768(2), 114-131.
• Süleymanoğlu, N., Ustabaş, R., Direkel, Ş., Alpaslan, Y. B., and Ünver, Y. (2017). 1, 2, 4-triazole derivative with Schiff base; thiol-thione tautomerism, DFT study and antileishmanial activity. Journal of Molecular Structure, 1150, 82-87.
• Şahin, Z. S., Şenöz, H., Tezcan, H., and Büyükgüngör, O. (2015). Synthesis, spectral analysis, structural elucidation and quantum chemical studies of (E)-methyl-4-[(2-phenylhydrazono) methyl] benzoate. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 143, 91-100.
• Wang, Z., Tang, P., Chen, S., Xing, Y., Yin, C., Feng, J., and Jiang, F. (2023). Fully biobased sustainable elastomers derived from chitin, lignin, and plant oil via grafting strategy and Schiff-base chemistry. Carbohydrate Polymers, 305, 120577.
• Wolff, S.K., Grimwood, D.J., McKinnon, J.J., Jayatilaka, D, Spackman, M.A. (2012). CrystalExplorer 3.1, University of Western Australia, Perth, Australia.
• Yekhlef, R., Benghanem, F., Foudia, M., Keraghel, S., Ghedjati, S., Toukal, L., and Akhtar, M. S. (2023). Synthesis, Spectroscopic and Thermal Characterization and Antioxidant Activities of Three Schiff Bases Derived from Aminophenol. International Journal of Heat and Technology, 41(2).