X-Rays, Spectroscopic and Molecular Docking Studies on Single Crystal Compounds Containing Schiff Base

Abstract

2,2'-((1E,1'E)-(ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))bis(4-(trifluoromethoxy)phenol single crystal containing Schiff base and thiazole ring was synthesized in this work. The synthesized crystalline structure was confirmed using IR spectroscopic and X-ray analysis techniques. It has been found that the analyzed compound may be two different tautomer forms such as phenol-imine and keto-amine. All experimental and theoretical studies were made on the two tautomeric structures. For this purpose, IRC (intrinsic reaction coordinate) and frontier molecular orbital (FMO) calculations were performed after the structural parameters of the title compound were optimized using GAUSSIAN 09W package program and DFT/B3LYP theory. In the IRC study, it was observed that the phenol-imine form had lower energy than the keto-amine form and the energy difference between the two forms was calculated as -14.71 kj/mol. HOMO energy values of phenol-imine and keto-amine forms was calculated as -6.31 and -5.77 eV, respectively. Finally, Molecular Docking study was performed for the 2RKV protein structure to be an inhibitory agent for the antifungal activity studies of the two tautomer forms. As a result of this calculation, the affinity values of the phenol-imine and keto-amine form (Docking score) were obtained as -7.7 and -7.3 kcal / mol, respectively, and it was observed in our study that the HOMO orbital energies and the affinity values were proportional.

Keywords

• Gaussian 09W,Phenol–imine,Keto–amine,Molecular docking

Schiff Bazı İçeren Tek Kristal Bileşik Üzerinde X-Işınları, Spektroskopik ve Moleküler Doking Çalışmaları

Abstract

Schiff bazı ve tiyazol halkası içeren 2,2'-((1E,1'E)-(ethan-1,2-dibis(azaneliden))bis(methaneliden))bis(4-(trifloromethoksi)fenol tek kristali bu çalışmada sentezlenmiştir. Sentezlenen kristalin yapısı, IR spektroskopik ve X-ışınları analizi teknikleri kullanılarak aydınlatılmıştır. İncelenen bileşiğin fenol–imin ve keto–amin gibi iki farklı tautomer formda olabileceği görülmüştür. Deneysel ve teorik tüm çalışmalar iki tautomer yapı üzerinde yapılmıştır. Bunun içinde bileşiğin yapısal parametreleri, GAUSSIAN 09W paket programı ve DFT/B3LYP teorisi ile optimize edildikten sonra IRC (intrinsic reaction coordinate), frontier moleküler orbital(FMO) hesaplamaları yapılmıştır. IRC çalışmasında fenol-imin formunun keto-amin formuna göre daha düşük enerjiye sahip olduğu gözlenmiş olup iki form arasındaki enerji farkı -14.71 kj/mol olarak hesaplanmıştır. Ayrıca, fenol-imin ve keto-amin formlarına ait HOMO enerji değerleri sırasıyla, -6.31 ve -5.77 eV olarak hesaplanmıştır. Son olarak da iki tautomer yapının antifungal aktivite çalışmaları için 2RKV protein yapısına inhibitör ajan olabilmesi yönünde Moleküler Doking çalışması yapılmıştır. Bu hesaplama sonucunda fenol-imin ve keto-amin formuna ait affinite değerleri (Doking skoru) sırasıyla, -7.7 ve -7.3 kcal/mol olarak elde edilmiş olup HOMO orbital enerjileri ile affinite değerlerinin orantılı olduğu çalışmamızda gözlenmiştir.

Keywords

• Gaussian 09W,Fenol–imin,Keto–amin,Moleküler doking

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