Journals / Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering / 2015 / Cilt: 16 - Sayı: 1
MICROWAVE ASSISTED and TRADITIONAL SYNTHESIS and CHARACTERIZATION of 2-ALLYL-6,6'-[(3,3'-DIMETHOXY[1,1'-BIPHENYL]-4,4'- DIYL)BIS(NITRILOMETHYLIDYNE)]BIS-PHENOL and EXPERIMENTAL and THEORETICAL INVESTIGATION of ITS TAUTOMERIC PROPERTIES
- Pages
- 81–96
- DOI
- —
Abstract
Schiff base compound 2-allyl-6,6'-[(3,3'-dimethoxy[1,1'-biphenyl]-4,4'diyl)bis(nitrilomethylidyne)]bis-phenol (3) was synthesized using traditional heating and microwaveirradiation method with the condensation reaction of 3-allylsalicylaldehyde (1) and o-dianisidine (2).The chemical structure of compound (3) was characterized by elemental analysis, FTIR,1H NMR and13C NMR techniques. The tautomeric equilibria (for phenol-imine O-H...N and keto-amine O... H-Ntautomers) in various organic solvents were studied using UV-visible region spectrophotometric methodand keto-amine percentages were calculated. Furthermore, the geometry of compound, the energies ofphenol-imine and keto-amine tautomers in different organic solvents, intramolecular O-H...N and O...HN hydrogen bond length, UV-visible excitation energy and oscillator strength were calculated with thetheoretical calculation method DFT (B3LYP)/6-311+G(d,p) and calculations were compared withexperimental results
Özet
2-Allil-6,6'-[(3,3'-dimetoksi[1,1'-bifenil]-4,4'-diyil)bis(nitrilometiliden)]bis-fenol (3) Schiff bazı bileşiği, 3-allilsalisilaldehitin (1) o-dianisidin (2) ile kondenzasyon reaksiyonundan geleneksel ısıtma ve mikrodalga-ışınlama yöntemi kullanılarak sentezlendi. Bileşik (3)’ün kimyasal yapısı element analizi, FTIR, 1H NMR, ve 13C NMR teknikleri kullanılarak karakterize edildi. Bileşiğin farklı organik çözücülerde fenol-imin (O-H…N) ve keto-amin (O…H-N) tautomerik dengeleri, UV-görünür bölge spektrofotometrik yöntem kullanılarak incelendi ve keto-amin yüzdeleri hesaplandı. Ayrıca, bileşiğin geometrisi, farklı çözücülerdeki fenol-imin ve keto-amin tautomerlerinin enerjisi, moleküliçi O-H…N ve O…H-N hidrojen bağ uzunluğu, UV-görünür bölge uyarılma enerjisi ve ossilatör kuvveti DFT (B3LYP)/6-311+G(d,p) hesaplama yöntemiyle teorik olarak hesaplandı ve hesaplamalar deneysel sonuçlar ile karşılaştırıldı.