Synthesis and Theoretical Studies of 2-Ethoxy-6-[(E)-[(2-Hydroxyphenyl)imino]methyl]phenol Derivative Schiff Bases

Öz

2-Ethoxy-6-[(E)-[(2-hydroxyphenyl)imino]methyl]phenol derivative Schiff bases (4-chloro-2-((3-ethoxy-2-hydroxybenzylidene)amino)phenol; 5S1 and 2-((3-ethoxy-2-hydroxybenzylidene)amino)-4-methylphenol; 5S2 have been synthesized and characterized with 1H-NMR, 13C-NMR, IR and elemental analysis in this study. The stable conformers and possible tautomer forms of Schiff base derivatives have been determined in theoretical calculations. All the calculations considering for the energetically stable conformers were performed with Gaussian09 program by using B3LYP/6-311g(2d,p) level of theory. The Gibbs Free energies, stable tautomer forms, H-bond, Mulliken charges, dipole moments, solvent accessibility surface areas (SAS), molecular electrostatic potential values, HOMO, LUMO and band gap energies (EGAP) were also calculated. The consistency between the theoretical and experimental 1H-NMR, 13C-NMR and IR spectra has also been investigated.

Anahtar Kelimeler

• Schiff base
• DFT
• SAS
• MEP
• HOMO-LUMO

2-Etoksi-6-[(E)-[(2-Hidroksifenil)imino]metil]fenol Türevi Schiff Bazlarının Sentezi ve Teorik Çalışmalar

Öz

2-Etoksi-6-[(E)-[(2-hidroksifenil)imino]metil]fenol türevi Schiff bazları (4-kloro-2-((3-etoksi-2-hidroksibenziliden)amino)fenol; 5S1 ve 2-((3-etoksi-2-hidroksibenziliden)amino)-4-metilfenol); 5S2 bileşikleri sentezlenmiştir. Karekterizasyonu 1H ve 13C NMR, elemental analiz ve FT-IR Spektrometresi ile yapılmıştır. Bileşiklerin ve olası tautomer formlarının kararlı konformasyonları teorik hesaplamalarla belirlenmiştir. Tüm hesaplamalar; kararlı konformasyonlar kullanılarak ve vakumda B3LYP/6-311g(2d,p) yöntemiyle yapılmıştır. Hesaplamalarda bileşiklerin enerjileri, kararlı taotomer formları, H-bağları, Mulliken yükleri, dipol momentleri, Çözücüyle erişilebilen yüzey alanı (Solvent accessibility surface), Moleküler elektrostatik potansiyel değerleri (MEP) (Molecular electrostatic potentials values), HOMO, LUMO ve enerji bant aralığı enerjileri (HOMO, LUMO and band gap energies) hesaplamaları yapılmıştır. Deneysel ve teorik IR, 1H ve 13C NMR uyumu incelenmiştir.

Anahtar Kelimeler

• Schiff bazı
• DFT
• SAS
• MEP
• HOMO-LUMO

Kaynakça

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