2-((2-Hidroksibenziliden)amino)-4-Nitrofenol Schiff Bazının Teorik Olarak İncelenmesi ve Bazı Quantum Kimyasal Parametrelerinin Hesaplanması
Yıl 2021,
, 685 - 698, 30.12.2021
Halil Berber
,
Ülkü Dilek Uysal
Öz
2-((2-Hidroksibenziliden)amino)-4-nitrofenol Schiff bazı bileşiğinin konformasyon analizi; DFT yönteminde, B3LYP metodu ve 6-311G++(d,p) temel seti ile yapılmış ve bileşiğin cis ve trans izomerlerinin konformasyonları teorik olarak hesaplanarak en kararlı konformasyonlar belirlenmiştir. Toplam enerjileri ve dihedral açıları hesaplanarak keto ve enol formlarının tautomer kararlılıkları belirlenmiştir. Enol tautomer formundaki molekülün keto tautomer formuna dönmesi sürecindeki enerji değişimleri yorumlanmıştır. Bileşiğin kararlı konformasyonu ile IR, 1H ve 13C NMR, UV-Vis., dipol moment, H-bağları, atomik yükleri (NBO), HOMO, LUMO ve bant aralığı enerjileri (EGAP), moleküler elektrostatik potansiyel şekli (MEP) ve çözücü erişilebilir yüzey alanı (SASA) hesaplamaları yapılmıştır. Molekülün optik ve metalik iletkenlik gibi elektronik özelliklere sahip aday molekül olduğu düşünülmektedir. SASA şeklinden molekülün polar ve polar protik çözücülerle güçlü etkileşim merkezlerinin olduğu ve biyolojik sistemler için de aktif merkezler içerdiği düşünülmektedir.
Destekleyen Kurum
Eskişehir Teknik Üniversitesi Bilimsel Araştırma Projeleri Komisyonu
Teşekkür
Bu çalışmanın yazarları, 20ADP188 numaralı proje çalışmaları kapsamındaki desteklerinden dolayı Eskişehir Teknik Üniversitesi Bilimsel Araştırma Projeleri Komisyonu Başkanlığına teşekkür ederler. Yazarlar Anadolu Üniversitesi Bilimsel Araştırma Projesi (BAP No 1102F027) kapsamında alınan Gaussian 09 ve Gauss View 5.0 programını (Proje No: 1304F064) bu çalışmada kullandıklarından Anadolu Üniversitesi Bilimsel Araştırma Projeleri Komisyon Başkanlığına da teşekkür ederler.
Kaynakça
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- [2] Sidir, I., Gülseven Sidir, Y., Khan, N. Berber, H. 2021. Optoelectronic And Photonic Properties Of Π-Conjugated Benzonitrile Derivative Bis-Schiff Base By Solution Technique, Optik. International Journal for Light and Electron Optics, 241, 166825.
- [3] Sidir, I., Sidir, Y. G., Berber, H., Demiray, F. 2019. Electronic Structure And Optical Properties Of Schiff Base Hydrazone Derivatives By Solution Technique For Optoelectronic Devices: Synthesis, Experiment And Quantum Chemical Investigation. Journal of Molecular Structure, 1176, 31-46.
- [4] Bin, H., Yao, J., Yang, Y., Angunawela, I., Sun, C., Gao, L. Ye, L., Qiu, B., Xue, L., Zhu, C., Yang, C., Zhang, Z. G,. Ade, H. 2018. High-Efficiency All-Small-Molecule Organic Solar Cells Based On An Organic Molecule Donor With Alkylsilyl-Thienyl Conjugated Side Chains. Advanced Materials, 30(27) 1706361.
- [5] Berhanu, A. L., Mohiuddin, G. I., Malik, A. K., Aulakh, J. S., Kumar, V., Kim, K. H. 2019. A review of the applications of Schiff bases as optical chemical sensors. Trac-Trends in Analytical Chemistry, 116, 74-91.
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- [7] Sidir, Y. G., Pirbudak, G., Berber, H., Sidir, I. 2017. Study on Electronic and Photophysical Properties of Substitute-((2-Phenoxybenzylidene)Amino)Phenol Derivatives: Synthesis, Solvatochromism, Electric Dipole Moments And DFT Calculations. Journal of Molecular Liquids, 242, 1096-1110.
- [8] Liua, Y., Maoa, L., Yang, S., Liu, M., Huang, H., Wen, Y., Deng, F., Li, Y., Zhang, X., Wei, Y. 2018. Synthesis and Biological Imaging of Fluorescent Polymeric Nanoparticles with AIE Feature via The Combination of RAFT Polymerization and Post-Polymerization Modification, Dyes and Pigments, 158, 79-87.
- [9] Gowda, A., Roy, A., Kumar, S. 2017. Synthesis and Mesomorphic Properties of Novel Schiff Base Liquid Crystalline EDOT Derivatives. Journal of Molecular Liquids, 225, 840–847.
- [10] Liu, X., Hamon, J. R. 2019. Recent Developments In Penta-, Hexa- And Heptadentate Schiff Base ligands and Their Metal Complexes. Coordination Chemistry Reviews, 389, 94-118.
- [11] Abdel-Rahman, L. H., Abu-Dief, A. M., Aboelez, M. O., Hassan Abdel-Mawgoud, A. A. 2017. DNA Interaction, Antimicrobial, Anticancer Activities and Molecular Docking Study of Some New VO(II), Cr(III), Mn(II) And Ni(II) Mononuclear Chelates Encompassing Quaridentate Imine Ligand. Journal of Photochemistry and Photobiology B-Biolog, 170, 271–285.
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- [14] Ercengiz, D., Berber, H., Uysal U. D. 2017. Theoretical IR, UV, 1H And 13C-NMR Spectra Of Certain Schiff Bases Derived Substituted-2-Aminophenol and Hydroxyl Benzaldehyde. Chemical Sciences Journal Open Access, 8(2), 102.
- [15] Uysal, U. D., Berber, H., Ercengiz, D. 2018. Theoretical Investigation on Solvent Dependent Shift and Electronic Transition Properties of Certain Schiff Bases. Journal of the Turkish Chemical Society, Section A, 4(1), 111-130.
- [16] Berber, H., Aydoğdu Erdönmez, A., Uysal, U. D. 2020. 2-Etoksi-6-[(E)-[(2-Hidroksifenil)imino]metil]fenol Türevi Schiff Bazlarının Sentezi ve Teorik Çalışmalar (Synthesis and Theoretical Studies of 2-Ethoxy-6-[(E)-[(2-Hydroxyphenyl)imino]methyl]phenol Derivative Schiff Bases). Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 24(2), 419-431.
- [17] Uysal, U. D., Ercengiz, D., Karaosmanoğlu, O., Berber, B., Sivas, H., Berber, H. 2021. Theoretical And Experimental Electronic Transition Behaviour Study of 2-((4-(Dimethylamino)Benzylidene)Amino)-4-Methylphenol and Its Cytotoxicity. Journal of Molecular Structure, 1227.
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- [19] Kianfar, A. H., Paliz, M., Roushani, M., Shamsipur, M. 2011. Synthesis, Spectroscopy, Electrochemistry and Thermal Study of Vanadyl Tridentate Schiff Base Complexes. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 82(1), 44-48.
- [20] Mandhare, D. B., Barhate, V. D. 2016. Development of Extractive Spectrophotometric Method For The Determination Of İron (III) With Schiff Base 2-[(2-Hydroxyphenylimino) Methyl]-4-Nitrophenol. International Journal of Current Pharmaceutical Research, 8(4), 89-91.
- [21] Mandhare, D. B., Barhate, V. D. 2016. Development of Extractive Spectrophotometric Method for The Determination of Manganese (II) with Schiff Base 2-[(2-Hydroxyphenylimino)Methyl]-4-Nitrophenol. European Journal of Biomedical and Pharmaceutical Sciences, 3(3), 421-423.
- [22] Mandhare, D. B., Barhate, V. D. 2015. Development of Extractive Spectrophotometric Method for The Determination Of Ruthenium (III) with Schiff Base 2-[(2-Hydroxyphenylimino) Methyl]-4-Nitrophenol. Journal of Applicable Chemistry, 4 (4), 1243-1247.
- [23] Fasina, T. M., Ejiah, F. N., Dueke-Eze, C. U., Idika, N. 2013. Substituent Effect on The Antimicrobial Activity of Schiff Bases Derived drom 2-Aminophenol and 2-Aminothiophenol. International Journal of Biological Chemistry, 7 (2), 79-85.
- [24] Ercengiz, D. 2019. Alüminyumun orto hidroksi schıff bazları kullanılarak spektrofotometrik tayinleri, Eskişehir Teknik Üniversitesi, Lisansüstü Eğitim Enstitüsü, Yüksek Lisans Tezi, 84s, Eskişehir.
- [25] Aydoğdu Erdönmez, A. 2019. Sübstitüe 2-aminofenol ve hidroksi benzaldehitten türetilen Schiff bazı ile alüminyumun spektrofotometrik tayini, Anadolu Üniversitesi, Lisansüstü Eğitim Enstitüsü, Yüksek Lisans Tezi, 83s, Eskişehir.
- [26] Sübstitüe 2-aminofenol ile sübstitüe hidroksi benzaldehit türevi bileşiklerinden oluşan bazı Schiff bazlarının sentezi, spektroskopik çalışması ve çeşitli numunelerde metal tayininde kullanımının araştırılması. 1509F633 Proje Yürütücülüğü (genel amaçlı proje), 25.12.2015-01.12.2017.
- [27] Berber, H., Uysal, U. D., Aydoğdu, A. 2017. Theoretical Study on The Stability, Acidity Constants and Molecular Electronic Properties of Certain O-Hydroxy Schiff Bases and Their Tautomers. Journal of the Turkish Chemical Society, Section A’, 4 (1), 77-92.
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The Conformation Analysis and Certain Theoretical Calculations of 2-((2-hydroxybenziliden)amino)-4-nitrophenol
Yıl 2021,
, 685 - 698, 30.12.2021
Halil Berber
,
Ülkü Dilek Uysal
Öz
A conformation analysis of Schiff base compound 2-((2-hydroxybenziliden)amino)-4-nitrophenol was done by DFT (B3LYP method and 6-311G++(d,p) basis set) method and possible cis and trans conformations were also calculated theoretically. Then the most stable conformation was determined. By calculating total energies and dihedral angles, the tautomer stabilities of keto and enol forms of the molecules were determined. The energy changes during conversion of the molecule in the form of an enol tautomer, to the keto form has been interpreted. The IR, 1H, 13C NMR and UV-Vis. spectra, dipole moment, H-bond, natural bond orbital (NBO), HOMO, LUMO and bant gap energy (EGAP), solvent accessibility surface (SASA) and molecular electrostatic potentials values (MEP) were calculated for the most stable conformation of the molecule. From its SASA shape, the molecule is thought to have strong interaction centers with polar and polar protic solvents and to contain active centers for biological systems. The molecule is thought to be a candidate molecule with electronic properties such as optical and metallic conductivity.
Kaynakça
- [1] Kaltenbrunner, M., White, M.S., Głowacki, E.D., Sekitani, T., Someya, T., Sarıçiftçi, N.S., Bauer, S. 2012. Ultrathin And Lightweight Organic Solar Cells With High Flexibility. Nature Communications, 3(770), 1–7.
- [2] Sidir, I., Gülseven Sidir, Y., Khan, N. Berber, H. 2021. Optoelectronic And Photonic Properties Of Π-Conjugated Benzonitrile Derivative Bis-Schiff Base By Solution Technique, Optik. International Journal for Light and Electron Optics, 241, 166825.
- [3] Sidir, I., Sidir, Y. G., Berber, H., Demiray, F. 2019. Electronic Structure And Optical Properties Of Schiff Base Hydrazone Derivatives By Solution Technique For Optoelectronic Devices: Synthesis, Experiment And Quantum Chemical Investigation. Journal of Molecular Structure, 1176, 31-46.
- [4] Bin, H., Yao, J., Yang, Y., Angunawela, I., Sun, C., Gao, L. Ye, L., Qiu, B., Xue, L., Zhu, C., Yang, C., Zhang, Z. G,. Ade, H. 2018. High-Efficiency All-Small-Molecule Organic Solar Cells Based On An Organic Molecule Donor With Alkylsilyl-Thienyl Conjugated Side Chains. Advanced Materials, 30(27) 1706361.
- [5] Berhanu, A. L., Mohiuddin, G. I., Malik, A. K., Aulakh, J. S., Kumar, V., Kim, K. H. 2019. A review of the applications of Schiff bases as optical chemical sensors. Trac-Trends in Analytical Chemistry, 116, 74-91.
- [6] Kajal, A., Bala, S., Kamboj, S., Sharma, N., Saini, V. 2013. Review Article: Schiff bases: A versatile pharmacophore. Journal of Catalysis, 893512, 1-14.
- [7] Sidir, Y. G., Pirbudak, G., Berber, H., Sidir, I. 2017. Study on Electronic and Photophysical Properties of Substitute-((2-Phenoxybenzylidene)Amino)Phenol Derivatives: Synthesis, Solvatochromism, Electric Dipole Moments And DFT Calculations. Journal of Molecular Liquids, 242, 1096-1110.
- [8] Liua, Y., Maoa, L., Yang, S., Liu, M., Huang, H., Wen, Y., Deng, F., Li, Y., Zhang, X., Wei, Y. 2018. Synthesis and Biological Imaging of Fluorescent Polymeric Nanoparticles with AIE Feature via The Combination of RAFT Polymerization and Post-Polymerization Modification, Dyes and Pigments, 158, 79-87.
- [9] Gowda, A., Roy, A., Kumar, S. 2017. Synthesis and Mesomorphic Properties of Novel Schiff Base Liquid Crystalline EDOT Derivatives. Journal of Molecular Liquids, 225, 840–847.
- [10] Liu, X., Hamon, J. R. 2019. Recent Developments In Penta-, Hexa- And Heptadentate Schiff Base ligands and Their Metal Complexes. Coordination Chemistry Reviews, 389, 94-118.
- [11] Abdel-Rahman, L. H., Abu-Dief, A. M., Aboelez, M. O., Hassan Abdel-Mawgoud, A. A. 2017. DNA Interaction, Antimicrobial, Anticancer Activities and Molecular Docking Study of Some New VO(II), Cr(III), Mn(II) And Ni(II) Mononuclear Chelates Encompassing Quaridentate Imine Ligand. Journal of Photochemistry and Photobiology B-Biolog, 170, 271–285.
- [12] Utreja, D., Singh, S., Kaur, M., 2015. Schiff Bases and their Metal Complexes as Anti-Cancer Agents: A Review. Current Bioactive Compounds, 11(4), 215–230.
- [13] Aydoğdu, A., Uysal, U. D., Berber, H. 2017. Newly Synthesized Schiff Bases: Structure Analysis, Theoretical IR, UV, 1H, 13C-NMR Spectra and Structure-Activity Relationship. Chemical Sciences Journal Open Access, 8(2), 98.
- [14] Ercengiz, D., Berber, H., Uysal U. D. 2017. Theoretical IR, UV, 1H And 13C-NMR Spectra Of Certain Schiff Bases Derived Substituted-2-Aminophenol and Hydroxyl Benzaldehyde. Chemical Sciences Journal Open Access, 8(2), 102.
- [15] Uysal, U. D., Berber, H., Ercengiz, D. 2018. Theoretical Investigation on Solvent Dependent Shift and Electronic Transition Properties of Certain Schiff Bases. Journal of the Turkish Chemical Society, Section A, 4(1), 111-130.
- [16] Berber, H., Aydoğdu Erdönmez, A., Uysal, U. D. 2020. 2-Etoksi-6-[(E)-[(2-Hidroksifenil)imino]metil]fenol Türevi Schiff Bazlarının Sentezi ve Teorik Çalışmalar (Synthesis and Theoretical Studies of 2-Ethoxy-6-[(E)-[(2-Hydroxyphenyl)imino]methyl]phenol Derivative Schiff Bases). Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 24(2), 419-431.
- [17] Uysal, U. D., Ercengiz, D., Karaosmanoğlu, O., Berber, B., Sivas, H., Berber, H. 2021. Theoretical And Experimental Electronic Transition Behaviour Study of 2-((4-(Dimethylamino)Benzylidene)Amino)-4-Methylphenol and Its Cytotoxicity. Journal of Molecular Structure, 1227.
- [18] Argauer, R. J., White, C. E. 1964. Effect of Substituent Groups on Fluorescence of Metal Chelates. Analytıcal Chemistry, 36(11), 2141-2144.
- [19] Kianfar, A. H., Paliz, M., Roushani, M., Shamsipur, M. 2011. Synthesis, Spectroscopy, Electrochemistry and Thermal Study of Vanadyl Tridentate Schiff Base Complexes. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 82(1), 44-48.
- [20] Mandhare, D. B., Barhate, V. D. 2016. Development of Extractive Spectrophotometric Method For The Determination Of İron (III) With Schiff Base 2-[(2-Hydroxyphenylimino) Methyl]-4-Nitrophenol. International Journal of Current Pharmaceutical Research, 8(4), 89-91.
- [21] Mandhare, D. B., Barhate, V. D. 2016. Development of Extractive Spectrophotometric Method for The Determination of Manganese (II) with Schiff Base 2-[(2-Hydroxyphenylimino)Methyl]-4-Nitrophenol. European Journal of Biomedical and Pharmaceutical Sciences, 3(3), 421-423.
- [22] Mandhare, D. B., Barhate, V. D. 2015. Development of Extractive Spectrophotometric Method for The Determination Of Ruthenium (III) with Schiff Base 2-[(2-Hydroxyphenylimino) Methyl]-4-Nitrophenol. Journal of Applicable Chemistry, 4 (4), 1243-1247.
- [23] Fasina, T. M., Ejiah, F. N., Dueke-Eze, C. U., Idika, N. 2013. Substituent Effect on The Antimicrobial Activity of Schiff Bases Derived drom 2-Aminophenol and 2-Aminothiophenol. International Journal of Biological Chemistry, 7 (2), 79-85.
- [24] Ercengiz, D. 2019. Alüminyumun orto hidroksi schıff bazları kullanılarak spektrofotometrik tayinleri, Eskişehir Teknik Üniversitesi, Lisansüstü Eğitim Enstitüsü, Yüksek Lisans Tezi, 84s, Eskişehir.
- [25] Aydoğdu Erdönmez, A. 2019. Sübstitüe 2-aminofenol ve hidroksi benzaldehitten türetilen Schiff bazı ile alüminyumun spektrofotometrik tayini, Anadolu Üniversitesi, Lisansüstü Eğitim Enstitüsü, Yüksek Lisans Tezi, 83s, Eskişehir.
- [26] Sübstitüe 2-aminofenol ile sübstitüe hidroksi benzaldehit türevi bileşiklerinden oluşan bazı Schiff bazlarının sentezi, spektroskopik çalışması ve çeşitli numunelerde metal tayininde kullanımının araştırılması. 1509F633 Proje Yürütücülüğü (genel amaçlı proje), 25.12.2015-01.12.2017.
- [27] Berber, H., Uysal, U. D., Aydoğdu, A. 2017. Theoretical Study on The Stability, Acidity Constants and Molecular Electronic Properties of Certain O-Hydroxy Schiff Bases and Their Tautomers. Journal of the Turkish Chemical Society, Section A’, 4 (1), 77-92.
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- [33] Erdik, E. 2015. Organik Kimyada Spektroskopik Yöntemler. 5. Baskı, Gazi Kitabevi Ankara.
- [34] Infrared Spectroscopy Absorption Table, https://chem.libretexts.org/Ancillary_Materials/Reference/Reference_Tables/Spectroscopic_Parameters/Infrared_Spectroscopy_Absorption_Table (Erişim Tarihi: 02.07.2021).
- [35] IR Spectrum Table & Chart, https://www.sigmaaldrich.com/TR/en/technical-documents/technical-article/analytical-chemistry/photometry-and-reflectometry/ir-spectrum-table (Erişim Tarihi: 02.07.2021).
- [36] Balcı, M. 2015. Nükleer Manyetik Rezonans Spektroskopisi. ODTÜ Geliştirme Vakfı Yayıncılık-Akademik Kitaplar, ISBN: 97897570642372007, Ankara, Ender Erdik, Organik Kimyada Spektroskopik Yöntemler, 5. Baskı, Gazi Kitabevi, Ankara.
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- [39] Christie, R. M. 2001. Colour Chemistry. 2nd editiom. Heriot-Watt University, Scottish Borders Campus, Galashiels, UK, The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge, CB40WF, UK, 333s.