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

doi:10.18038/btda.70064

TR EN

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

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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Details

Primary Language

Turkish

Subjects

Engineering

Journal Section

Research Article

Authors

Emel Ermiş

Publication Date

April 25, 2016

Submission Date

November 27, 2015

Acceptance Date

-

Published in Issue

Year 2016 Volume: 17 Number: 1

DOI

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

IZ

https://izlik.org/JA62YR78HL

APA

Ermiş, E. (2016). 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. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 17(1), 79-95. https://doi.org/10.18038/btda.70064

AMA

1.Ermiş E. 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. AUJST-A. 2016;17(1):79-95. doi:10.18038/btda.70064

Chicago

Ermiş, Emel. 2016. “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”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17 (1): 79-95. https://doi.org/10.18038/btda.70064.

EndNote

Ermiş E (June 1, 2016) 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. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17 1 79–95.

IEEE

[1]E. Ermiş, “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”, AUJST-A, vol. 17, no. 1, pp. 79–95, June 2016, doi: 10.18038/btda.70064.

ISNAD

Ermiş, Emel. “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”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17/1 (June 1, 2016): 79-95. https://doi.org/10.18038/btda.70064.

JAMA

1.Ermiş E. 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. AUJST-A. 2016;17:79–95.

MLA

Ermiş, Emel. “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”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, vol. 17, no. 1, June 2016, pp. 79-95, doi:10.18038/btda.70064.

Vancouver

1.Emel Ermiş. 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. AUJST-A. 2016 Jun. 1;17(1):79-95. doi:10.18038/btda.70064

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