Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule with Experimental and Theoretical Methods

Year 2019, Volume: 9 Issue: 1, 99 - 112, 28.06.2019

Halil Uğur Taşdemir , Fatih Sevgi , Ercan Türkkan

Abstract

In this study, the conformational analysis was performed by the
semi-empirical PM3 method to determine the molecular structure of the glyoxime
molecule. Each of conformer  is optimized using
the Density Functionals Theory (DFT) with DFT / B3LYP / 6-311G ++ (d, p) method
basis set combination. As a result of the optimization, the most stable
structure was determined according to the energy order. The
chemical shift values ​​of ¹H and ¹³C, which are Nuclear
Magnetic Resonance (NMR) parameters of this stable structure, were calculated
in liquid phase and gas phase using DFT method and six different basis sets. Furthermore, the effect of intermolecular
hydrogen bonding on ¹H chemical shift values ​​was investigated by
dimer molecular modeling at the level of B3LYP / 6-31G ++ (d, p) in the DFT
method. The ¹H and ¹³C chemical shift values ​​of the
glyoxime molecule were determined experimentally. Structural analyzes of the
glyoxime molecule were made by comparing the calculated NMR parameters with the
experimental NMR parameters.

Keywords

Glyoxime, Nuclear Magnetic Resonance, Density Functional Theory, Hydrogen Bonding

Glioksim Molekülünün 1H ve 13C NMR Kimyasal Kayma Değerlerinin Deneysel ve Teorik Metotlar ile Belirlenmesi

Abstract

Bu çalışmada glioksim molekülünün moleküler yapısını belirlemek için konformasyon analizi yarı deneysel PM3 metodu ile yapılmıştır. Elde edilen konformasyonlar Yoğunluk Fonksiyonelleri Metodu (DFT) kullanılarak DFT/B3LYP/6-311G++(d,p) metot baz seti kombinasyonu ile optimize edilmiştir. Optimizasyon sonucunda enerji durumuna göre en kararlı yapı bulunmuştur. Bu kararlı yapıya ait Nükleer Manyetik Rezonans (NMR) parametreleri olan 1H ve 13C kimyasal kayma değerleri, DFT metodu ve 6 farklı baz seti kullanılarak sıvı fazda ve gaz fazında hesaplanmıştır. Ayrıca moleküller arası hidrojen bağının, 1H kimyasal kayma değerlerine etkisi DFT metodunda B3LYP/ 6-31G++(d,p) seviyesinde dimer moleküler modellemesi yapılarak incelenmiştir. Aynı zamanda glioksim molekülünün 1H ve 13C kimyasal kayma değerleri deneysel olarak da tespit edilmiştir. Hesaplanan NMR parametreleri ile deneysel NMR parametreleri karşılaştırılarak glioksim molekülünün yapı analizleri yapılmıştır.

Keywords

Glioksim, Nükleer manyetik rezonans, Yoğunluk fonksiyonelleri teorisi, Hidrojen bağı

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