Synthesis, spectral characterization, theoretical analysis and antioxidant activities of aldol derivative isophorone structures

Abstract

In this study, the structural properties of isophorone derivatives with π-conjugation obtained by aldol reactions have characterized by spectral analyses such as FT-IR, ¹H-NMR, and ¹³C-NMR.  The compounds have optimized using Density Functional Theory (DFT/B3LYP) method with 6-311G(d,p) basis set in the ground state and the geometric parameters have compared with the results obtained by X-ray Single Crystal diffraction technique.  Also, the spectral results have examined along with calculated vibrational frequencies, ¹H-NMR, ¹³C-NMR chemical shift values. To get information about the chemical stability of the compounds, some of the structure parameters (ionization potential, electron affinity, electronegativity, chemical hardness-softness, etc.) have been studied at the same theoretical level. Also, NLO properties and antioxidant activities of the compounds have investigated by using DPPH free radical scavenging, reducing power and metal chelating methods. Spectral and theoretical results are compatible with each other.

Keywords

• Isophorone
• spectral analysis
• DFT
• antioxidant activity

Aldol türevi izoforan yapılarının sentezi, spektral karakterizasyonu, teorik analizi ve antioksidan aktiviteleri

Abstract

Bu çalışmada, aldol tepkimeleri ile elde edilen π konjugasyonuna sahip izoforan türevlerinin yapısal özellikleri FT-IR, ¹H-NMR ve ¹³C-NMR gibi spektral analizler ile karakterize edilmiştir. Yoğunluk Fonksiyoneli Teorisi (YFT/B3LYP) kullanılarak 6-311G(d,p) baz seti ile taban durumunda optimize edilmiş ve geometrik parametreleri, X-ışını Tek Kristal difraksiyon yöntemi ile gerçekleştirilen kristal yapı analizinin sonuçları ile karşılaştırılmıştır. Ayrıca spektral sonuçlar, teorik olarak hesaplanan titreşim frekansları, ¹H-NMR ve ¹³C-NMR kimyasal kayma değerleri ile birlikte incelenmiştir.  Bileşiklerin kimyasal kararlılığı hakkında bilgi sahibi olabilmek için bir takım yapı parametreleri (iyonlaşma potansiyeli, elektron ilgisi,  elektronegatiflik, kimyasal sertlik-yumuşaklık, v.b.) kuramsal düzeyde incelenmiştir. Bileşiklerin NLO özellikleri ve antioksidan aktiviteleri; DPPH serbest radikal giderme, indirgeme gücü ve metal şelatlama metotları kullanılarak incelenmiştir.  Spektral ve kuramsal sonuçlar birbiriyle uyumludur. 

Keywords

• İzoforan
• spektral analiz
• YFT
• antioksidan aktivite

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