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

Yıl 2017, Cilt: 19 Sayı: 3, 89 - 104, 07.12.2017

Serpil Eryılmaz , Melek Gül , Ersin İnkaya

https://doi.org/10.25092/baunfbed.363772

Cited By: 3

Öz

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.

Anahtar Kelimeler

Isophorone, spectral analysis, DFT, antioxidant activity

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

Öz

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. 

Anahtar Kelimeler

İzoforan, spektral analiz, YFT, antioksidan aktivite

Kaynakça

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