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Journals / Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering / 2016 / Cilt: 17 - Sayı: 1

MICROWAVE ASSISTED SYNTHESIS and CHARACTERIZATION of 6,6 '- {OXYBIS [(pPHENYLENE)IMINOMETHYL]}BIS-(2-tert-BUTYL PHENOL), EXPERIMENTAL and THEORETICAL INVESTIGATION of ITS TAUTOMERIC AND SOLVATOCHROMIC PROPERTIES

6,6′-{OKSİBİS[(p-FENİLEN)İMİNOMETİL]}BİS-(2-tert-BÜTİLFENOL) SCHIFF BAZININ MİKRODALGA IŞINLAMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU, TAUTOMERİK ve SOLVATOKROMİK ÖZELLİKLERİNİN DENEYSEL VE TEORİK OLARAK İNCELENMESİ

Emel Ermiş
Pages
79–95
Publication Date
2016-04-25
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Furthermore, the structure of compound, the energies of phenol-imine/ phenol-imine and keto-amine/keto-amine tautomers in different organicsolvents, intramolecular O−H....N and O....H−N hydrogen bond length, UV-visible excitation energy and oscillator strength werecalculated with the theoretical DFT method (B3LYP)/6-311+G(d,p) and calculations were compared with experimental results.It was determined theoretically and experimentally that the compound (3) exhibits the phenol-imine/phenol-imine tautomeric structure and solvatochromic feature in selected organic solvents.

📌 3 Key Takeaways

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Objective & Hypothesis:The synthesis of 6,6'-{oxybis[(p-phenylene)iminomethyl]}bis-(2-tert-butylphenol) (3) was performed from the condensation reaction of 3-tert-butylsalicylaldehyde (1) with 4,4'-diaminodiphenyl ether (2) using the microwave-irradiation method.
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Key Findings & Data:The structure of compound (3) was characterized by elemental analysis, FTIR, 1H NMR, 13C NMR and UV-visible spectroscopic techniques.
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Conclusion & Impact:Furthermore, the structure of compound, the energies of phenol-imine/ phenol-imine and keto-amine/keto-amine tautomers in different organicsolvents, intramolecular O−H....N and O....H−N hydrogen bond length, UV-visible excitation energy and oscillator strength werecalculated with the theoretical DFT method (B3LYP)/6-311+G(d,p) and calculations were compared with experimental results.It was determined theoretically and experimentally that the compound (3) exhibits the phenol-imine/phenol-imine tautomeric structure and solvatochromic feature in selected organic solvents.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:3-ter-Bütilsalisilaldehit · 4'-Diaminodifenil eter · Mikrodalga-ışınlama yöntemi

Abstract

The synthesis of 6,6'-{oxybis[(p-phenylene)iminomethyl]}bis-(2-tert-butylphenol) (3) was performed from the condensation reaction of 3-tert-butylsalicylaldehyde (1) with 4,4'-diaminodiphenyl ether (2) using the microwave-irradiation method. The structure of compound (3) was characterized by elemental analysis, FTIR, 1H NMR, 13C NMR and UV-visible spectroscopic techniques. The tautomeric equilibria (for phenol-imine O−H....N and keto-amine O....H−N tautomers) and the behavior of solvatochromic in different organic solvents were studied using UV visible spectrophotometric method. Furthermore, the structure of compound, the energies of phenol-imine/ phenol-imine and keto-amine/keto-amine tautomers in different organicsolvents, intramolecular O−H....N and O....H−N hydrogen bond length, UV-visible excitation energy and oscillator strength werecalculated with the theoretical DFT method (B3LYP)/6-311+G(d,p) and calculations were compared with experimental results.It was determined theoretically and experimentally that the compound (3) exhibits the phenol-imine/phenol-imine tautomeric structure and solvatochromic feature in selected organic solvents.

Özet

3-tert-Bütilsalisilaldehitin (1) 4,4'-diaminodifenil eter (2) ile kondenzasyon reaksiyonundan yararlanılarak 6,6′-{oksibis[(p-fenilen)iminometil]}bis-(2-tert-bütilfenol) (3) sentezi, mikrodalga-ışınlama yöntemi kullanılarak gerçekleştirilmiştir. Bileşik (3)’ün kimyasal yapısı element analizi, FTIR, 1H NMR, 13C NMR ve UV-görünür bölge spektroskopi teknikleri kullanılarak karakterize edilmiştir. Bileşiğin farklı organik çözücülerde fenol-imin (O−H….N) ve keto-amin (O….H−N) tautomerik dengeleri ve solvatokromik özelliği UV-görünür bölge spektrofotometrik yöntem kullanılarak incelenmiştir. Ayrıca, bileşiğin geometrisi, farklı çözücülerdeki fenol-imin/fenol-imin ve keto-amin/keto-amin tautomerlerinin enerjisi, molekül içi O−H….N ve O….H−N hidrojen bağ uzunlukları, UV-görünür bölge uyarılma enerjisi ve ossilatör kuvveti DFT (B3LYP)/6-311+G(d,p) hesaplama yöntemi kullanılarak hesaplanmıştır ve hesaplamalar deneysel sonuçlar ile karşılaştırılmıştır. Bileşik (3)’ün seçilen organik çözücülerde fenol-imin/fenol-imin tautomer formunu tercih ettiği ve solvatokromik özellik sergilediği deneysel ve teorik olarak belirlenmiştir.

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Cite This Article

Ermiş, E. (2016). MICROWAVE ASSISTED SYNTHESIS and CHARACTERIZATION of 6,6 '- {OXYBIS [(pPHENYLENE)IMINOMETHYL]}BIS-(2-tert-BUTYL PHENOL), EXPERIMENTAL and THEORETICAL INVESTIGATION of ITS TAUTOMERIC AND SOLVATOCHROMIC PROPERTIES. Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering, Cilt: 17 - Sayı: 1, 79–95. https://ajindex.com/articles/196958

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