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

Year 2019, Volume: 23 Issue: 2, 505 - 514, 25.08.2019

Tuncay Karakurt , Seher Meral Ayşen Alaman Ağar

https://doi.org/10.19113/sdufenbed.530279

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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