Bazı yeni Schiff bazı moleküllerinin sentezi karakterizasyonu spektroskopik özelliklerinin deneysel ve kuramsal incelenmesi
Küçük Resim Yok
Tarih
2022
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Bursa Teknik Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Schiff bazları günümüze kadar kimya, biyoloji, eczacılık ve tıp gibi alanlarda dikkat çeken kimyasal bileşikler grubudur ve aldehit veya keton varlığında birincil aminler ile reaksiyon sonucunda elde edilirler. İki basamakta gerçekleşen Schiff bazı bileşiği sentezlerinin ilk basamağı, karbonil karbonunun ve primer aminin kondenzasyonu, ikinci basamağı ise ilk basamakta oluşan bu ara ürün üzerinden imin bileşiği oluşumudur. Bu çalışmada ilk olarak 2-Asetonaftanon, 1-(2-Bromofenil)etanon, 1-(3,5-di-tert-butil-2-hidroksifenil)etan-1-on bileşiklerinin etanol çözeltisinde, zayıf asit katalizör varlığında izoforondiamin bileşiği ile reaksiyonundan üç tane yeni Schiff bazı ligandı sentezlenmiştir. Çalışmanın temel amacı, sentezi öngörülen yeni bileşiklerin deneysel olarak sentezlenmesi ve bu bileşiklerin yapılarının doğru bir şekilde aydınlatılarak, moleküllerin deneysel, kuramsal spektroskopik özelliklerinin karşılaştırılması ile beraber elektronik, kimyasal potansiyel, bağ uzunluğu, bağ açıları, elektronegatiflik gibi bazı fizikokimyasal özelliklerinin incelenmesidir. Elde edilen moleküllerin İTK ve IR, NMR, UV-Gör bölge spektroskopi teknikleri kullanılarak yapıları aydınlatılmıştır. Karbonil bileşiğinden Schiff bazına geçiş, reaksiyon sırasında ince tabaka kromotografisi ile belirli aralıklarla gözlemlenebilirken, IR spektrofotometresinde ise en belirgin özelliklerden biri karbonil bileşiklerindeki (C=O) grubuna ait spesifik 1680 ~ 1720 cm -1 karbonil bandının yerini imin grubu (C=N) 1550 ~ 1650 cm -1 bandı alarak karbonil grubuna ait bandın kaybolduğunun görülmesidir. NMR ve UV-Gör bölge yöntemlerinde de imin grubuna ait literatüre dayanan belirgin özellikler tespit edilebilmektedir. Sentez çalışmalarının ve deneysel analizlerin tamamlanmasından sonra ikinci aşama olarak sentezlenen moleküllerin kuramsal hesaplamalarına geçilmiş, bu hesaplamalar için Gaussian 09 paket programı Yoğunluk Fonksiyonel Teoremi (YFK) kullanılarak literatürde organik moleküller için en uygun olduğu bilinen B3LYP metodu ile 6-311++G (d, p) taban kümesi seçilmiştir. Sentezlenen moleküllerin spin çokluğu, toplam yük sıfır alınarak singlet olarak belirlenmiş ve kararlı moleküllerin optimizasyonları yapılarak diğer kuramsal hesaplar bu yapılar üzerinden gerçekleştirilmiştir. Schiff bazlarına ait IR, 1H-NMR, 13C-NMR, UV-Gör bölge spektroskopileri ile bağ uzunlukları, bağ açıları, elektrostatik potansiyel, HOMO-LUMO değerleri, doğal bağ orbital atomik yükleri ile kimyasal parametreler gibi bazı fizikokimyasal özellikleri hesaplanarak deneysel verilerle karşılaştırılıp yorumlanmıştır.
Schiff bases are a group of chemical compounds that have attracted attention in fields such as chemistry, biology, pharmacy and medicine, and they are obtained as a result of reaction with primary amines in the presence of aldehydes or ketones. The first step of the Schiff base compound synthesis, which takes place in two steps, is the condensation of the carbonyl carbon and the primary amine, and the second step is the formation of the imine compound over this intermediate product formed in the first step. In this study, firstly, 2-Acetonaptanone, 1-(2-Bromophenyl)ethanone, 1-(3,5-di-tert-butyl-2-hydroxyphenyl)ethan-1-one compounds were mixed with isophorondiamine compound in ethanol solution in the presence of weak acid catalyst. Three new Schiff base ligands were synthesized from the reaction. The main aim of the study is to experimentally synthesize new compounds whose synthesis is predicted, and to accurately illuminate the structures of these compounds, to compare experimental and theoretical spectroscopic properties of molecules, as well as to examine some physicochemical properties such as electronic, chemical potential, bond length, bond angles, electronegativity. The structures of the obtained molecules were elucidated by using TLC and IR, NMR, UV-Vis region spectroscopy techniques. While the transition from carbonyl compound to Schiff base can be observed with thin layer chromatography (TLC) at certain intervals during the reaction, in IR spectrophotometer, one of the most distinctive features is that the specific 1680 ~ 1720 cm-1 carbonyl band belonging to the (C=O) group in carbonyl compounds is replaced by the imine group (C=N) 1550 ~ 1650 cm-1 band, and the band belonging to the carbonyl group disappears. In NMR and UV-Vis region methods, distinctive features of the imine group based on the literature can be detected. After the synthesis studies and experimental analyzes were completed, the theoretical calculations of the synthesized molecules were started as the second step, for these calculations, using the Gaussian 09 package program Density Functional Theorem (DFT), the 6-311++G (d, p) base set was selected with the B3LYP method, which is known to be the most suitable for organic molecules in the literature. The spin multiplicity of the synthesized molecules was determined as singlet by taking the total charge to zero and other theoretical calculations were carried out on these structures by optimizing the stable molecules. Some physicochemical properties of Schiff bases such as bond lengths, bond angles, electrostatic potential, HOMO-LUMO values, natural bond orbital atomic charges and chemical parameters were calculated by IR, 1H-NMR, 13C-NMR, UV-Vis region spectroscopic methods and compared with experimental data.
Schiff bases are a group of chemical compounds that have attracted attention in fields such as chemistry, biology, pharmacy and medicine, and they are obtained as a result of reaction with primary amines in the presence of aldehydes or ketones. The first step of the Schiff base compound synthesis, which takes place in two steps, is the condensation of the carbonyl carbon and the primary amine, and the second step is the formation of the imine compound over this intermediate product formed in the first step. In this study, firstly, 2-Acetonaptanone, 1-(2-Bromophenyl)ethanone, 1-(3,5-di-tert-butyl-2-hydroxyphenyl)ethan-1-one compounds were mixed with isophorondiamine compound in ethanol solution in the presence of weak acid catalyst. Three new Schiff base ligands were synthesized from the reaction. The main aim of the study is to experimentally synthesize new compounds whose synthesis is predicted, and to accurately illuminate the structures of these compounds, to compare experimental and theoretical spectroscopic properties of molecules, as well as to examine some physicochemical properties such as electronic, chemical potential, bond length, bond angles, electronegativity. The structures of the obtained molecules were elucidated by using TLC and IR, NMR, UV-Vis region spectroscopy techniques. While the transition from carbonyl compound to Schiff base can be observed with thin layer chromatography (TLC) at certain intervals during the reaction, in IR spectrophotometer, one of the most distinctive features is that the specific 1680 ~ 1720 cm-1 carbonyl band belonging to the (C=O) group in carbonyl compounds is replaced by the imine group (C=N) 1550 ~ 1650 cm-1 band, and the band belonging to the carbonyl group disappears. In NMR and UV-Vis region methods, distinctive features of the imine group based on the literature can be detected. After the synthesis studies and experimental analyzes were completed, the theoretical calculations of the synthesized molecules were started as the second step, for these calculations, using the Gaussian 09 package program Density Functional Theorem (DFT), the 6-311++G (d, p) base set was selected with the B3LYP method, which is known to be the most suitable for organic molecules in the literature. The spin multiplicity of the synthesized molecules was determined as singlet by taking the total charge to zero and other theoretical calculations were carried out on these structures by optimizing the stable molecules. Some physicochemical properties of Schiff bases such as bond lengths, bond angles, electrostatic potential, HOMO-LUMO values, natural bond orbital atomic charges and chemical parameters were calculated by IR, 1H-NMR, 13C-NMR, UV-Vis region spectroscopic methods and compared with experimental data.
Açıklama
Lisansüstü Eğitim Enstitüsü, Kimya Ana Bilim Dalı
Anahtar Kelimeler
Kimya, Chemistry
