Siringaldehit bazlı 2,4,6-triarilpiridinlerin sentezi, antioksidan etki ve teorik hesaplama çalışmaları
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2023
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Düzce Üniversitesi
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Abstract
ÖZET SİRİNGALDEHİT BAZLI 2,4,6-TRİARİLPİRİDİNLERİN SENTEZİ, ANTİOKSİDAN ETKİ VE TEORİK HESAPLAMA ÇALIŞMALARI Esra Nur ALBAYRAK Düzce Üniversitesi Lisansüstü Eğitim Enstitüsü, Kimya Anabilim Dalı Yüksek Lisans Tezi Danışman: Doç. Dr. Alparslan ATAHAN Temmuz 2023, 78 sayfa Bu tezde, siringaldehitten türetilen sekiz adet yeni 2,4,6-triarilpiridin türevi bileşik tasarlandı ve bu yapılar tek basamaklı multi-komponent bir yöntem kullanılarak başarıyla sentezlendi. Bunun için, siringaldehit bileşiği amonyum asetat varlığında farklı metil keton türevleri ile geri soğutucu altında ve DMF içerisinde reaksiyona sokuldu. Elde edilen her bir piridin türevinin yapısı 1H-NMR, 13C-NMR ve FTIR teknikleri kullanılarak aydınlatıldı. Yapıları aydınlatılan bu bileşiklerin antioksidan aktiviteleri literatürde yaygın olarak kullanılan yöntemlere göre ve bilinen referans bileşiklerle kıyaslanarak belirlendi. Daha sonra, elde edilen yapıların bilgisayar destekli teorik kuantum hesaplamaları gerçekleştirildi. Bu hesaplamalar B3LYP teorisi ve SVP ile TZVP temel setleri kullanılarak su ve gaz fazlarında kapsamlı şekilde tamamlandı. Ayrıca bu hesaplamalarda sertlik, yumuşaklık, HOMO-LUMO enerji seviyeleri gibi önerilen yapıların elektronik doğasının ve biyoaktivite sonuçlarının anlaşılmasında son derece önemli moleküler tanımlayıcılar olan teorik parametreler ortaya konuldu. Ardından bu çalışma için en önemli tanımlayıcılardan biri olan ve radikal yakalama potansiyelini tanımlayan Fukui indisi adlı elektronik yapı tanımlayıcı parametreler belirlendi. Son olarak, teorik olarak hesaplanan ve deneysel olarak elde edilen sonuçlar birlikte değerlendirilerek tez çalışması kapsamındaki bileşikler için yapı-aktivite ilişkisi ortaya konuldu. Sonuç olarak, bu çalışma kapsamındaki bileşikler yapı aktivite ilişkisi çerçevesinde değerlendirilerek elde edilen tüm serinin antioksidan ajanlar olarak kullanılabilme potansiyeli ortaya konuldu. Anahtar sözcükler: Siringaldehit, Piridin, Antioksidan, DFT, Fukui indisleri
ABSTRACT SYNTHESIS, ANTIOXIDANT EFFECT AND THEORETICAL CALCULATION STUDIES OF SYRINGALDEHYDE BASED 2,4,6-TRIARYPYRIDINES Esra Nur ALBAYRAK Düzce University Graduate School of Natural and Applied Sciences, Department of Chemistry Master's Thesis Supervisor: Assoc. Prof. Dr. Alparslan ATAHAN July 2023, 78 pages In this thesis, eight new 2,4,6-triarylpyridine derivative compounds derived from syringaldehyde were designed and these structures were successfully synthesized by using one-step multi-component method. For this, syringaldehyde compound was reacted with different methyl ketone derivatives in the presence of ammonium acetate under reflux and in DMF. The structure of each obtained pyridine derivative was elucidated using 1H-NMR, 13C-NMR and FTIR techniques. The antioxidant activities of these compounds, whose their structures were elucidated, were determined according to the methods commonly used in the literature and by comparing them with known reference compounds. Then, computer aided theoretical quantum calculations of the obtained structures were carried out. These calculations have been extensively completed in the water and gas phases using B3LYP theory and the SVP and TZVP basis sets. In addition, in these calculations, theoretical parameters such as hardness, softness, HOMO-LUMO energy levels, which are extremely important molecular descriptors for understanding the electronic nature and bioactivity results of the proposed structures, were revealed. Then, electronic structure descriptive parameters called Fukui indices, which is one of the most important descriptors for this study and defines the radical capture potential, were determined. Finally, the structure-activity relationship for the compounds within the scope of the thesis study was revealed by evaluating the theoretically calculated and experimentally obtained results together. As a result, the compounds in this study were evaluated within the framework of structure-activity relationship, and the potential of using the whole series as antioxidant agents was revealed. Keywords: Syringaldehyde, Pyridine, Antioxidant, DFT, Fukui indices
ABSTRACT SYNTHESIS, ANTIOXIDANT EFFECT AND THEORETICAL CALCULATION STUDIES OF SYRINGALDEHYDE BASED 2,4,6-TRIARYPYRIDINES Esra Nur ALBAYRAK Düzce University Graduate School of Natural and Applied Sciences, Department of Chemistry Master's Thesis Supervisor: Assoc. Prof. Dr. Alparslan ATAHAN July 2023, 78 pages In this thesis, eight new 2,4,6-triarylpyridine derivative compounds derived from syringaldehyde were designed and these structures were successfully synthesized by using one-step multi-component method. For this, syringaldehyde compound was reacted with different methyl ketone derivatives in the presence of ammonium acetate under reflux and in DMF. The structure of each obtained pyridine derivative was elucidated using 1H-NMR, 13C-NMR and FTIR techniques. The antioxidant activities of these compounds, whose their structures were elucidated, were determined according to the methods commonly used in the literature and by comparing them with known reference compounds. Then, computer aided theoretical quantum calculations of the obtained structures were carried out. These calculations have been extensively completed in the water and gas phases using B3LYP theory and the SVP and TZVP basis sets. In addition, in these calculations, theoretical parameters such as hardness, softness, HOMO-LUMO energy levels, which are extremely important molecular descriptors for understanding the electronic nature and bioactivity results of the proposed structures, were revealed. Then, electronic structure descriptive parameters called Fukui indices, which is one of the most important descriptors for this study and defines the radical capture potential, were determined. Finally, the structure-activity relationship for the compounds within the scope of the thesis study was revealed by evaluating the theoretically calculated and experimentally obtained results together. As a result, the compounds in this study were evaluated within the framework of structure-activity relationship, and the potential of using the whole series as antioxidant agents was revealed. Keywords: Syringaldehyde, Pyridine, Antioxidant, DFT, Fukui indices
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Kimya, Chemistry
