Analysis of the Molecular Structure of N'-((2-hydroxynaphthalen-1-yl)methylene)isobutyrohydrazide

Yıl 2022, , 592 - 608, 31.08.2022

Çiğdem Yüksektepe Ataol

https://doi.org/10.18185/erzifbed.1123429

Öz

Bu çalışmada kapalı formülü C15H16N2O2 olan N'-((2-hidroksinaftalin-1-yl)metilen)izobütirohidrazid bileşiğinin moleküler yapısı Yoğunluk Fonksiyonel Teorisi (YFT) hibrid baz fonksiyonlarından B3LYP ve 6-311+G(d, p) baz seti kullanılarak araştırılmıştır. C15H16N2O2 bileşiğinin moleküler yapısı, ilk olarak gaz, kloroform, etanol ve su ortamlarında optimize edilmiştir. Daha sonra optimize edilen moleküler yapılar kullanılarak moleküler elektrostatik potansiyel (MEP) haritası elde edilmiş, farklı çözücü ortamlarında moleküler orbital enerji seviyeleri ve enerji değerleri araştırılmıştır. Farklı ortamlar için elde edilen moleküler orbital enerji değerlerinden kimyasal reaktivite parametreleri türetilmiştir. Zamana Bağlı Yoğunluk Fonksiyonel Teorisi (ZB-YFT) kullanılarak farklı ortamlar için bileşiğin uyarılmış durumda UV spektraları hesaplatılmış ve moleküler orbitallere atomik orbitallerden yüzde katkılar hesaplatılmıştır. Son olarak, moleküler yapının (ΔN) yük transfer ve (ΔE) enerji düşürme değerleri kullanılarak Sn, Hg, Cd ve Zn gibi bazı ağır metaller ile C15H16N2O2 bileşiği arasındaki etkileşim araştırılmıştır.

Anahtar Kelimeler

density functional theory, chemical reactivity, ligand-metal interaction

Kaynakça

• Andronie, L. Pop, I. Mireşan, V. Coroian, A. Raducu, C. Cocan, D. Coroian, C.O. (2014). “Adsorption behavior of 1- and 2- Naphthol species on Ag colloidal nanoparticles”. Human & Veterinary Medicine International Journal of the Bioflux Society, 6(4), 210-213.
• Boukli-Hacene, F., Merad, M., Ghalem, S. and Soufi, W. (2014). “DFT study of the interaction of Cu(II), Zn(II), Sn(II) with carbohydrates in aqueous solution”. J. Chem. Chem. Eng., 8: 1009-1017.
• Demircioğlu, Z. Albayrak Kaştaş, Ç. Büyükgüngör O. (2015). “Theoretical analysis (NBO, NPA, Mulliken Population Method) and molecular orbital studies (hardness, chemical potential, electrophilicity and Fukui function analysis) of (E)-2-((4-hydroxy-2-methylphenylimino)methyl)-3-methoxyphenol”. J. Mol. Struct., 1091, pp. 183-195.
• Frisch, M.J. et al., Gaussian 09, Wallingford (CT, USA): Gaussian, Inc., (2009).
• Kanmazalp, S.D. Başaran, E. Karaküçük-Iyidoğan, A. Oruç-Emre, E.E. & Dege, N. (2017). “X-ray structures and spectroscopic properties of chiral thiosemicarbazides as studied by computational calculations”. Phosphorus, Sulfur, and Silicon and the Related Elements, 192(7), 856-865.
• Kanmazalp, S.D. Başaran, E. Karaküçük-Iyidoğan, A. Oruç-Emre, E.E. Sen, F. and Dege, N. (2018). “Synthesis, characterization, spectroscopy, X-ray structure and gaussian hybrid computational investigation of (−)-(S)-1-[2-(benzenesulfonamido)-3-phenylpropanoyl]-4-[(4-methyl)phenyl]thiosemicarbazide”. Phosphorus, Sulfur, and Silicon and the Related Elements 193(10), 675–684.
• Kanmazalp, S.D. Macit, M. Dege, N. (2019). “Hirshfeld surface, crystal structure and spectroscopic characterization of (E)-4-(diethylamino)-2-((4-phenoxyphenylimino)methyl)phenol with DFT studies”. Journal of Molecular Structure 1179, 181-191.
• Lee, C. Yang, W. Parr, R.G. (1988). “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density”. Phys. Rev. B37, 785.
• Moraes, R.S. Aderne, R.E. Cremona, M. Rey, N.A. (2016). “Luminescent properties of a dihydrazone derived from the antituberculosis agent isoniazid: Potentiality as an emitting layer constituent for OLED fabrication”. Opt. Mater. 52, 186–191.
• Pekparlak, A. Tamer, O. Kanmazalp, S.D. Berber, N. Arslan, M. Avcı, D. Dege, N. Tarcan, E. Atalay, Y. (2018). “Crystal structure, spectroscopic (FT-IR, 1H and 13C NMR) characterization and density functional theory calculations on Ethyl 2-(dichloromethyl)-4-methyl-1-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carboxylate”. Journal of Molecular Structure, 1171, 762-770.
• Singh, D., Ahmad, S. and Singh, P. P. (2009). “DFT based calculation of interaction energy between metal halides and organic bases”. J. Mol. Struc. Theochem., 905: 13-23.
• Tai, X.S. Wang, X. (2015). “Synthesis and crystal structure of a 1D-chained coordination polymer constructed from Ca2+ and 2-[(E)-(2-furoylhydrazono)methyl]benzenesulfonate”. Crystals, 5, 458–465.
• Yang, Y.G. Hong, M. Xu, L.D. Cui, J.C. Chang, G.L. Li, D.C. Li, C.Z. (2016). “Organotin(IV) complexes derived from Schiff base N1-[(1E)-(2-hydroxy-3- methoxyphenyl)methylidene]pyridine-3-carbohydrazone: Synthesis, in vitro cytotoxicities and DNA/BSA interaction”. J. Organomet. Chem. 804, 48–58.
• Yüksektepe Ataol, Ç. and Zülfikaroğlu, A. (2021). “The Structure Analysis by DFT and X-ray Diffraction”. LAMBERT Academic Publishing. ISBN: 978-613-5-84392-7. 1-57.
• Zulfikaroglu, A, Bati, H., Dege, N. (2018). “A theoretical and experimental study on isonitrosoacetophenone nicotinoyl hydrazone: Crystal structure, spectroscopic properties, NBO, NPA and NLMO analyses and the investigation of interaction with some transition metals” Journal of Molecular Structure, 1162, 125-139.
• Zülfikaroglu, A. (2020a). “The synthesis, experimental and theoretical characterization of a Pd(II) complex from diacetyl monoxime isobutyrohydrazone”. Journal of Molecular Structure 1209, 127950.
• Zülfikaroglu, A. (2020b), “DFT Computational Studies on Some Cobaloximes” Erzincan University Journal of Science and Technology 13(3), 1299-1316.
• Zülfikaroğlu, A. and Yüksektepe Ataol, Ç. (2020). “Synthesis, Crystal Structure and Dft Studies of (E)-N'-(3,4-Dihydroxybenzylidene)Isobutyrohydrazide” Hydrazones Uses and Reactions, Nova Science Publishers. ISBN: 978-1-53617-672-8. 21-56.