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Pimaran iskeletine sahip leusofleoksol bileşiğinin yapısal, spektroskopik ve elektronik özelliklerinin DFT/HF yöntemleriyle incelenmesi Skip to content Yıl 2024, Cilt: 26 Sayı: 2, 581 – 593, 15.07.2024
Alper Kaya Akın Azizoğlu
Öz Bu çalışma kapsamında, pimaran ana iskeletine sahip leusofleoksol bileşiği Gaussian programı kullanılarak YFT ve ab-initio teorik hesaplama yöntemleriyle incelenmiştir. İlgili bileşiğin literatürde bulunan deneysel bağ uzunluğu, bağ açı, dihedral açı değerleriyle, HF, B3LYP, WB97XD yöntemleriyle gaz fazında elde edilen teorik veriler karşılaştırılmıştır. İstatiksel analiz çalışmaları sonucunda bağ uzunluklarının incelenmesinde en başarılı hesapsal yöntemin HF ve 6-31G düzeyinin olduğu tespit edilmiştir. Bununla birlikte, leusofleoksol bileşiğinin bağ ve dihedral açılarını tespitinde en uygun hesapsal yöntemin WB97XD/6-31G metodunun olduğu belirlenmiştir. Ayrıca leusofleoksolun deneysel infrared spektrumunda gözlenen sinyaller, B3LYP/cc-pVDZ düzeyinde titreşim analizi yapılarak irdelenmiştir. 13C-NMR ppm değerleri de, teorik olarak WB97XD/(6-31G), B3LYP/(cc-pVDZ), B3LYP/(6-31G), ve HF/(6-31G) düzeylerinde hesaplanmıştır. İstatiksel analiz çalışmaları sonucunda, 13C-NMR kimyasal kayma hesaplanmasında en iyi hesapsal yöntemlerin, WB97XD/(6-31G) ve B3LYP/(cc-pVDZ) düzeyleri olduğu sonucuna varılmıştır. Son olarak başlıkta belirtilen bileşiğin elektronik yapıları (HOMO-LUMO sınır orbitalleri ve MEP haritası) B3LYP/cc-pVDZ teori düzeyinde analiz edilmiştir.
Anahtar Kelimeler Diterpen, YFT, HF, MEP, IR
Destekleyen Kurum BAÜN BAP
Proje Numarası BAÜN BAP 2020/037
Teşekkür Bu çalışma, Balıkesir Üniversitesi tarafından desteklenmiştir, BAP Proje No: 2020/037. Desteklerinden dolayı Balıkesir Üniversitesi Bilimsel Araştırma Projeleri Birimi’ne teşekkürlerimi sunarım.
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A.02, Gaussian, Inc, Wallingford CT, (2016). Azizoglu, A., Özer, Z. ve Kilic, T., An experimental and theoretical study on siderol isolated from sideritis species, Collect. Czech. Chem. Commun., 76, 95–114, (2011). Azizoglu, A. ve Yildiz, C.B., Spectroscopic Structural Aromaticity and Electronic Properties of Isatoic Anhydride – Experimental and Theoretical Investigations, Indian J. Pure and Appl. Phys. 59, 437–446, (2021). K. Fukui, Theory of Orientation and Stereoselection, Springer-Verlag Press, New York, (1975). Szatylowicz, H., Wieczorkiewicz, P. A. ve Krygowski, T. M., Molecular geometry as a source of electronic structure of π-electron systems and their physicochemical properties, in Fernandez, I., Aromaticity: Modern Computational Methods and Applications, Elsevier Press, 71-99, New York, (2021). Azizoglu, A. ve Azizoglu, N., A Theoretical study on the Molecular and electronic structure of halogenated sumanene, Proceedings 2nd Int. Aegean Phys. Chem. Days, 113, Ayvalık, (2004). Kaya, A., Abietan ve pimaran iskeletine sahip bileşiklerin elektronik, moleküler yapılarının ve titreşim özelliklerinin teorik olarak incelenmesi, Yüksek Lisans Tezi, Balıkesir Üniversitesi, Fen Bilimleri Enstitüsü, Balıkesir, (2020). Silverstein, R. M. ve Webster, F. X., Spectroscopic Identification of Organic Compounds, John Wiley & Sons Ltd., New York, (2005). Timouri, A., Emami, M., Chermahini, A. N. ve Dabbagh, H. A., Spectrocopic quantum chemical DFT/HF study and synthesis of [2.2.1] hept-2-en-2-amino-N-azatricyclo[3.2.1.0] octane, Spectrochimica Acta Part A: Molecular and Biomolecular Spect., 71, 1749-1755, (2009). Odabasioglu, S., Kurtaran, R., Azizoglu, A., Kara, H., Oz, S., Atakol, O., Experimental and computational investigations of a cadmium(II) mononuclear complex with 2,6-bis(3,5-dimethyl-N-pyrazolyl)pyridine (bdmpp) and selenocyanate as ligands, Cent. Eur. J. Chem., 7, 402-409, (2009). Fleming, I., Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons Ltd., London, (1976). Çelik, M. S. ve Azizoğlu, A., Vibrational spectra and assingments of strained cyclic allenes investigated by theoretical methods, Proceedings Int. Conf. on Apps. in Chem. and Chem. Eng. ICACHE 2017, Saraybosna, Bosna Hersek, 27, (2017). Kassaee, M.Z., Zandi, H., Haerizade, B.N. ve Ghambarian, M., Effects of a-mono heteroatoms (N vs. P), and b-conjugation on cyclic silylenes, Comput. Theory Chem. 1001, 39–43, (2012). Alezzy, A. A., Al-horaibi, S. A., Alnahari, H. A., Al-Odayni, A. B., AlSaeedy, M., Al-Adhreai, A., Saeed, W., Alshawesh, G. ve Arif, P. M., Synthesis, characterization, and biological studies of novel N(cinnamylidene) sulfamethoxazole (SMZ-CAL) and its metal complexes, J. Mol. Struct., 1299, 137069-137069, (2024), Kalecik, Güzel, S. E., Doğan, O. E., Ağar, E. ve Yavuz, M., (E)-4-bromo-5-floro-2-(((4-(fenilamino)fenil)imino)metil)fenol bileşiğinin kimyasal aktivite ve spektroskopik çalışmaları, Karadeniz Fen Bilimleri Dergisi, 12, 821-840, (2022). Hamid, A. M. A., Amer, A. H., Assy, M. G., Zordok, W. A., Mouneir, S. M., El-Kalyoubi, S. ve Shehab, W. S., Synthesis, pharmacological evaluation, DFT calculation, and theoretical investigation of spirocyclohexane derivatives, Bioorganic Chem., 131, 106280, (2023). Aygün, M., Structural characterization and DFT studies of an oxazol-5-one derivative, BAUN Fen Bil. Enst. Dergisi, 20, 389-397, (2018). Politzer, P., Abrahmsen, L. ve Sjoberg, P, Effects of amino and nitro substituents upon the electrostatic potential of an aromatic ring, J. Am. Chem. Soc.,106, 855–860, (1984). Kaya, A. ve Azizoğlu, A., Abietan iskeletine sahip szemaoenoid A molekülünün teorik olarak incelenmesi, Süleyman Demirel Üniv. Fen Edebiyat Fak. Fen Dergisi, 17, 82-95, (2022). Kolancılar, H., DFT yöntemi kullanılarak 1,3-bis- {(2-aminobenzoil) amino} propanin teorik hesaplamaları ve bu değerlerin literatürdeki deneysel değerler ile karşılaştırılması, Düzce Üniv. Bilim ve Teknoloji Dergisi, 7, 3, 1319–1334, (2019). Saraç, K., 4-Klorometil-6,8-dimetilkumarin Bileşiğinin Sentezi ve Teorik Kimyasal Hesaplamaları, BEÜ Fen Bilimleri Dergisi, 7, 311–319, (2018).
The theoretical investigation of structural, spectroscopic and electronic properties of leucophleoxol compound having pimarane skeleton with DFT/HF methods Yıl 2024, Cilt: 26 Sayı: 2, 581 – 593, 15.07.2024
Alper Kaya Akın Azizoğlu
Öz Within the scope of this study, the leucophleoxol compound with the pimarane main skeleton was examined by DFT and ab-initio theoretical calculation methods using the Gaussian program. The experimental bond length, bond angle and dihedral angle values of the title compound found in the literature were compared with the theoretical data obtained in the gas phase by HF, B3LYP, and WB97XD methods. It has been determined that the HF/6-31G level is the most compatible theoretical method in determining bond lengths through statistical analysis studies. However, it has been defined that the most appropriate theoretical method to determine bond angles and dihedral angles is the WB97XD/(6-31G) level for the compound of leucophleoxol. Additionally, the signals observed in the experimental infrared spectrum of leucophleoxol were examined by vibration analysis at the B3LYP/(cc-pVDZ) level. 13C – NMR chemical shift values were calculated theoretically at the levels of WB97XD/6-31G, B3LYP/(cc-pVDZ), B3LYP/6-31G, and HF/6-31G. As a result of statistical analysis studies, it was concluded that the most appropriate theoretical methods for 13C-NMR chemical shift calculation are WB97XD/(6-31G) and B3LYP/(cc-pVDZ) levels. Finally, the electronic structures of the title compound (HOMO-LUMO frontier orbitals and MEP map) were analyzed at the B3LYP/(cc-pVDZ) level of theory.
Anahtar Kelimeler Diterpene, DFT, HF, MEP, IR
Proje Numarası BAÜN BAP 2020/037
Kaynakça Eksi, G., Kurbanoglu, S. ve Erdem, S. A., Analysis of diterpenes and diterpenoids, in Nabavi, S., Saeedi, M., Nabavi, S. ve Silva, A. S., Recent Advances in Natural Products Analysis, Elsevier Press, 313-345, Amsterdam, (2020). Çarıkçı, S., Kılıç, T., Gören, A. C., Dirmenci, T., Toraman, G. Ö. A. ve Topçu, G., Chemical profile of the Anatolian Sideritis species with bioactivity studies, Pharmaceutical Biology, 61, 1484-1511, (2023). Imran, I., Hussain, L., Zia-Ul-Haq, M, Janbaz, K. H., Gilani, A. H. ve Feo, V. D., Gastrointestial and respiratory activities of Acacia leucophloea, J. Ethnopharmacol., 138, 676–682, (2011). Azizoğlu, A., Özer, Z., Çarıkçı, S. ve Kılıç, T., Comparative experimental and theoretical study on the molecular structure and spectroscopic properties of sideroxol isolated from Sideritis stricta and its electronic properties. French-Ukrainian J. Chem., 9, 94–107, (2021). Çalışır, Ü. ve Çiçek B., Bazı yeni N-sübstitüe amino asit esterlerinin yapısal özelliklerinin in silico ile araştırılması, BAUN Fen Bil. Enst. Dergisi, 25, 748-760, (2023). Özer, Z. A., Kılıç, T., Çarıkçı, S., ve Azizoğlu, A., Synthesis Structural Characterization Spectroscopic Properties and Theoretical Investigations of Acetoxy Siderol. Russian J. Physical Chem. A, 93, 2703–2709, (2019). Çıtak, S. Özer, Z., Kılıç, T., Çarıkçı, S., ve Azizoğlu, Experimental and theoretical study on linearol isolated from Sideritis species, Revue Roumaine De Chimie, 59, 227–234, (2014). Bansal, R. K., Garcia-Alvarez, M. C., Joshi, K. C., Rodriguez, B. ve Patni, R., Diterpenoids from Acacia leucophloea, Phytochemistry, 19, 1979-1983, (1980). Carmen, M. D., Cano, F. H. ve Rodriguez, B., Diterpenoids from Acacia leucophloea: Revision of the structures of leucophleol and leucophleoxol, J. Nat. Prod., 64, 899–902, (2001). Frisch, M. J., Trucks, G. W., Schlegel, H. B.,et all. Gaussian 09, Rev. A.02, Gaussian, Inc, Wallingford CT, (2016). Azizoglu, A., Özer, Z. ve Kilic, T., An experimental and theoretical study on siderol isolated from sideritis species, Collect. Czech. Chem. Commun., 76, 95–114, (2011). Azizoglu, A. ve Yildiz, C.B., Spectroscopic Structural Aromaticity and Electronic Properties of Isatoic Anhydride – Experimental and Theoretical Investigations, Indian J. Pure and Appl. Phys. 59, 437–446, (2021). K. Fukui, Theory of Orientation and Stereoselection, Springer-Verlag Press, New York, (1975). Szatylowicz, H., Wieczorkiewicz, P. A. ve Krygowski, T. M., Molecular geometry as a source of electronic structure of π-electron systems and their physicochemical properties, in Fernandez, I., Aromaticity: Modern Computational Methods and Applications, Elsevier Press, 71-99, New York, (2021). Azizoglu, A. ve Azizoglu, N., A Theoretical study on the Molecular and electronic structure of halogenated sumanene, Proceedings 2nd Int. Aegean Phys. Chem. Days, 113, Ayvalık, (2004). Kaya, A., Abietan ve pimaran iskeletine sahip bileşiklerin elektronik, moleküler yapılarının ve titreşim özelliklerinin teorik olarak incelenmesi, Yüksek Lisans Tezi, Balıkesir Üniversitesi, Fen Bilimleri Enstitüsü, Balıkesir, (2020). Silverstein, R. M. ve Webster, F. X., Spectroscopic Identification of Organic Compounds, John Wiley & Sons Ltd., New York, (2005). Timouri, A., Emami, M., Chermahini, A. N. ve Dabbagh, H. A., Spectrocopic quantum chemical DFT/HF study and synthesis of [2.2.1] hept-2-en-2-amino-N-azatricyclo[3.2.1.0] octane, Spectrochimica Acta Part A: Molecular and Biomolecular Spect., 71, 1749-1755, (2009). Odabasioglu, S., Kurtaran, R., Azizoglu, A., Kara, H., Oz, S., Atakol, O., Experimental and computational investigations of a cadmium(II) mononuclear complex with 2,6-bis(3,5-dimethyl-N-pyrazolyl)pyridine (bdmpp) and selenocyanate as ligands, Cent. Eur. J. Chem., 7, 402-409, (2009). Fleming, I., Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons Ltd., London, (1976). Çelik, M. S. ve Azizoğlu, A., Vibrational spectra and assingments of strained cyclic allenes investigated by theoretical methods, Proceedings Int. Conf. on Apps. in Chem. and Chem. Eng. ICACHE 2017, Saraybosna, Bosna Hersek, 27, (2017). Kassaee, M.Z., Zandi, H., Haerizade, B.N. ve Ghambarian, M., Effects of a-mono heteroatoms (N vs. P), and b-conjugation on cyclic silylenes, Comput. Theory Chem. 1001, 39–43, (2012). Alezzy, A. A., Al-horaibi, S. A., Alnahari, H. A., Al-Odayni, A. B., AlSaeedy, M., Al-Adhreai, A., Saeed, W., Alshawesh, G. ve Arif, P. M., Synthesis, characterization, and biological studies of novel N(cinnamylidene) sulfamethoxazole (SMZ-CAL) and its metal complexes, J. Mol. Struct., 1299, 137069-137069, (2024), Kalecik, Güzel, S. E., Doğan, O. E., Ağar, E. ve Yavuz, M., (E)-4-bromo-5-floro-2-(((4-(fenilamino)fenil)imino)metil)fenol bileşiğinin kimyasal aktivite ve spektroskopik çalışmaları, Karadeniz Fen Bilimleri Dergisi, 12, 821-840, (2022). Hamid, A. M. A., Amer, A. H., Assy, M. G., Zordok, W. A., Mouneir, S. M., El-Kalyoubi, S. ve Shehab, W. S., Synthesis, pharmacological evaluation, DFT calculation, and theoretical investigation of spirocyclohexane derivatives, Bioorganic Chem., 131, 106280, (2023). Aygün, M., Structural characterization and DFT studies of an oxazol-5-one derivative, BAUN Fen Bil. Enst. Dergisi, 20, 389-397, (2018). Politzer, P., Abrahmsen, L. ve Sjoberg, P, Effects of amino and nitro substituents upon the electrostatic potential of an aromatic ring, J. Am. Chem. Soc.,106, 855–860, (1984). Kaya, A. ve Azizoğlu, A., Abietan iskeletine sahip szemaoenoid A molekülünün teorik olarak incelenmesi, Süleyman Demirel Üniv. Fen Edebiyat Fak. Fen Dergisi, 17, 82-95, (2022). Kolancılar, H., DFT yöntemi kullanılarak 1,3-bis- {(2-aminobenzoil) amino} propanin teorik hesaplamaları ve bu değerlerin literatürdeki deneysel değerler ile karşılaştırılması, Düzce Üniv. Bilim ve Teknoloji Dergisi, 7, 3, 1319–1334, (2019). Saraç, K., 4-Klorometil-6,8-dimetilkumarin Bileşiğinin Sentezi ve Teorik Kimyasal Hesaplamaları, BEÜ Fen Bilimleri Dergisi, 7, 311–319, (2018). Toplam 30 adet kaynakça vardır.
Ayrıntılar Birincil Dil Türkçe Konular Organik Kimya (Diğer) Bölüm Araştırma Makalesi Yazarlar Alper Kaya T.C. Milli Eğitim Bakanlığı Muş 0000-0003-2770-5468 Türkiye
Akın Azizoğlu Balıkesir Üniversitesi, Balıkesir, Türkiye 0000-0002-5098-1842 Türkiye
Proje Numarası BAÜN BAP 2020/037 Erken Görünüm Tarihi 14 Temmuz 2024 Yayımlanma Tarihi 15 Temmuz 2024 Gönderilme Tarihi 9 Mart 2024 Kabul Tarihi 3 Temmuz 2024 Yayımlandığı Sayı Yıl 2024 Cilt: 26 Sayı: 2
Kaynak Göster APA Kaya, A., & Azizoğlu, A. (2024). Pimaran iskeletine sahip leusofleoksol bileşiğinin yapısal, spektroskopik ve elektronik özelliklerinin DFT/HF yöntemleriyle incelenmesi. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 26(2), 581-593. AMA Kaya A, Azizoğlu A. Pimaran iskeletine sahip leusofleoksol bileşiğinin yapısal, spektroskopik ve elektronik özelliklerinin DFT/HF yöntemleriyle incelenmesi. BAUN Fen. Bil. Enst. Dergisi. Temmuz 2024;26(2):581-593. Chicago Kaya, Alper, ve Akın Azizoğlu. “Pimaran Iskeletine Sahip Leusofleoksol bileşiğinin yapısal, Spektroskopik Ve Elektronik özelliklerinin DFT/HF yöntemleriyle Incelenmesi”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 26, sy. 2 (Temmuz 2024): 581-93. EndNote Kaya A, Azizoğlu A (01 Temmuz 2024) Pimaran iskeletine sahip leusofleoksol bileşiğinin yapısal, spektroskopik ve elektronik özelliklerinin DFT/HF yöntemleriyle incelenmesi. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 26 2 581–593. IEEE A. Kaya ve A. Azizoğlu, “Pimaran iskeletine sahip leusofleoksol bileşiğinin yapısal, spektroskopik ve elektronik özelliklerinin DFT/HF yöntemleriyle incelenmesi”, BAUN Fen. Bil. Enst. Dergisi , c. 26, sy. 2, ss. 581–593, 2024. ISNAD Kaya, Alper – Azizoğlu, Akın. “Pimaran Iskeletine Sahip Leusofleoksol bileşiğinin yapısal, Spektroskopik Ve Elektronik özelliklerinin DFT/HF yöntemleriyle Incelenmesi”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 26/2 (Temmuz 2024), 581-593. JAMA Kaya A, Azizoğlu A. Pimaran iskeletine sahip leusofleoksol bileşiğinin yapısal, spektroskopik ve elektronik özelliklerinin DFT/HF yöntemleriyle incelenmesi. BAUN Fen. Bil. Enst. Dergisi . 2024;26:581–593. MLA Kaya, Alper ve Akın Azizoğlu. “Pimaran Iskeletine Sahip Leusofleoksol bileşiğinin yapısal, Spektroskopik Ve Elektronik özelliklerinin DFT/HF yöntemleriyle Incelenmesi”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, c. 26, sy. 2, 2024, ss. 581-93. Vancouver Kaya A, Azizoğlu A. Pimaran iskeletine sahip leusofleoksol bileşiğinin yapısal, spektroskopik ve elektronik özelliklerinin DFT/HF yöntemleriyle incelenmesi. BAUN Fen. Bil. Enst. Dergisi. 2024;26(2):581-93.
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