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

Year 2016, Volume: 17 Issue: 1, 79 - 95, 25.04.2016

Emel Ermiş

https://doi.org/10.18038/btda.70064

Cited By: 1

Abstract

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.

Keywords

3-ter-Bütilsalisilaldehit, 4, 4'-Diaminodifenil eter; Mikrodalga-ışınlama yöntemi; Tautomerik denge; Solvatokromizm; DFT.

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

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 organic
solvents, intramolecular O−H....N and O....H−N hydrogen bond length, UV-visible excitation energy and oscillator strength were
calculated 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.

Keywords

4,4'-Diaminodiphenyl ether, Microwave-irradiation method, Tautomeric equilibrium, Solvatochromism, DFT

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