The Conformation Analysis and Certain Theoretical Calculations of 2-((2-hydroxybenziliden)amino)-4-nitrophenol

Abstract

A conformation analysis of Schiff base compound 2-((2-hydroxybenziliden)amino)-4-nitrophenol was done by DFT (B3LYP method and 6-311G++(d,p) basis set) method and possible cis and trans conformations were also calculated theoretically. Then the most stable conformation was determined. By calculating total energies and dihedral angles, the tautomer stabilities of keto and enol forms of the molecules were determined. The energy changes during conversion of the molecule in the form of an enol tautomer, to the keto form has been interpreted. The IR, 1H, 13C NMR and UV-Vis. spectra, dipole moment, H-bond, natural bond orbital (NBO), HOMO, LUMO and bant gap energy (EGAP), solvent accessibility surface (SASA) and molecular electrostatic potentials values (MEP) were calculated for the most stable conformation of the molecule. From its SASA shape, the molecule is thought to have strong interaction centers with polar and polar protic solvents and to contain active centers for biological systems. The molecule is thought to be a candidate molecule with electronic properties such as optical and metallic conductivity.

Keywords

• Conformation analysis
• Schiff base
• Tautomerism
• H-bond
• NBO
• DFT

2-((2-Hidroksibenziliden)amino)-4-Nitrofenol Schiff Bazının Teorik Olarak İncelenmesi ve Bazı Quantum Kimyasal Parametrelerinin Hesaplanması

Abstract

2-((2-Hidroksibenziliden)amino)-4-nitrofenol Schiff bazı bileşiğinin konformasyon analizi; DFT yönteminde, B3LYP metodu ve 6-311G++(d,p) temel seti ile yapılmış ve bileşiğin cis ve trans izomerlerinin konformasyonları teorik olarak hesaplanarak en kararlı konformasyonlar belirlenmiştir. Toplam enerjileri ve dihedral açıları hesaplanarak keto ve enol formlarının tautomer kararlılıkları belirlenmiştir. Enol tautomer formundaki molekülün keto tautomer formuna dönmesi sürecindeki enerji değişimleri yorumlanmıştır. Bileşiğin kararlı konformasyonu ile IR, 1H ve 13C NMR, UV-Vis., dipol moment, H-bağları, atomik yükleri (NBO), HOMO, LUMO ve bant aralığı enerjileri (EGAP), moleküler elektrostatik potansiyel şekli (MEP) ve çözücü erişilebilir yüzey alanı (SASA) hesaplamaları yapılmıştır. Molekülün optik ve metalik iletkenlik gibi elektronik özelliklere sahip aday molekül olduğu düşünülmektedir. SASA şeklinden molekülün polar ve polar protik çözücülerle güçlü etkileşim merkezlerinin olduğu ve biyolojik sistemler için de aktif merkezler içerdiği düşünülmektedir.

Keywords

• Konformasyon analizi
• Schiff bazı
• Tautomerizm
• H-bağı
• NBO
• DFT

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