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

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.

References

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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

Year 2016, Volume: 17 Issue: 1, 79 - 95, 25.04.2016
https://doi.org/10.18038/btda.70064

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.

References

  • Layer RW. The chemistry of imines. Chemical Reviews 1963; 63: 489–510.
  • Ingold CK. Structure and Mechanism in Organic Chemistry, 2nd ed. Cornell Univ, Ithaca,1969.
  • Barton D, Ollis WD. Comprehensive Organic Chemistry. vol 2. Pergamon, Oxford, 1979.
  • Lozier RA, Bogomolni W, Stoekenius J. Bacteriorhodopsin: a light-driven proton pump in halobacterium halobium. Biophysical Journal 1975; 15: 955-962.
  • Walsh CT, Orme-Johnson WH. Nickel enzymes. Biochemistry 1987; 26(16): 4901–4906.
  • Costamagna J, Vargas J, Latorre R, Alvarado A, Mena G. Coordination compounds of copper, nickel and iron with Schiff bases derived from hydroxynaphthaldehydes and salicylaldehydes. Coordination Chemistry Reviews 1992; 119: 67-88.
  • Ünver H, Yıldız M, Dülger B, Özgen Ö, Kendi E, Durlu TN. Spectroscopic studies, antimicrobial activities and crystal structures of N-(2-hydroxy-3-methoxybenzalidene)1-aminonaphthalene. Journal of Molecular Structure 2005; 737: 159–164.
  • Omar MM, Mohemed GG, Ibrahim AA. Spectroscopic characterization of metal complexes of novel Schiff base. Synthesis, thermal and biological activity studies. Spectrochimica Acta A 2009; 73: 358–369. [9] Abdallah SM, Mohamed GG, Zayed MA, Abou El-Ela MS. Spectroscopic study of molecular structures of novel Schiff base derived from o-phthaldehyde and 2-aminophenol and its coordination compounds together with their biological activity. Spectrochimica Acta A 2009; 73(5): 833–840.
  • Taggi AE, Hafez AM, Wack H, Young B, Ferraris D, Lectka T. The development of the first catalyzed reaction of ketenes and imines:  Catalytic, asymmetric synthesis of β-Lactams. Journal of the American Chemical Society 2002; 124: 6626–6635.
  • Nejati K, Rezvani Z, Massoumi B. Syntheses and investigation of thermal properties of copper complexes with azo-containing Schiff-base dyes. Dyes Pigments 2007; 75: 653–657.
  • Ispir, E. (2009). The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing Schiff bases and their metal complexes. Dyes Pigments 82, 13–19.
  • Garnovskii AD, Nivorozhkin AL, Minkin VI. (1993). Ligand environment and the structure of schiff base adducts and tetracoordinated metal-chelates. Coordination Chemistry Reviews 1993; 126(1-2): 1-69. [14] Ogawa K, Harada J. Aggregation controlled proton tautomerization in salicylideneanilines. Journal of Molecular Structure 2003; 647: 211–216.
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  • Basu Baul TS, Das P, Chandra AK, Mitra S, Pyke S. The synthesis, characterization and structures of some 4-[((E)-1-{2-hydroxy-5-[(E)-2-(aryl)-1-diazenyl]phenyl} methylidene)amino]benzoic acid. Dyes and Pigments 2009; 82: 379–386.
  • Minkin VI, Tsukanov AV, Dubonosov AD, Bren VA. Tautomeric Schiff bases: Iono-, solvato-, thermo- and photochromism. Journal of Molecular Structure 2011; 998: 179–191.
  • Khanmohammadi H, Abdollahi A. New diaminomaleonitrile-based azo-azomethine dyes; synthesis, characterization and spectral properties. Dyes and Pigments 2012; 94: 163–168.
  • Moustakali-Mavridis I, Hadjoudis E, Mavridis A. Crystal and molecular structure of some thermochromic Schiff bases. Acta Crystallographica Section B 1978; 34: 3709-3715.
  • Hadjoudis E, Vitterakisp M, Mavridis IM. Photochromism and thermochromism of schiff bases in the solid state and in rigid glasses. Tetrahedron 1987; 43: 1345-1360.
  • Nicoud JF, Twieg RJ. Design and Synthesis of Organic Molecular Compounds for Efficient Second-Harmonic Generation. In: Chemla DS, Zyss J, editors. (1987). Nonlinear Optical Properties of Organic Molecules and Crystals. New York, Academic Press, vol. 1, 1987. (Chapter II-3), pp. 227-291. [24] Dürr H, Bouas-Laurent H. Photochromism: Molecules and Systems. 1st Ed. Elsevier, Amsterdam, 1990. [25] Alemi AA, Shaabani, B. Synthesis and characterization of a Schiff base of p-tert-butylcalıx[4]arene and its complex with copper(II). Acta Chimica Slovenica Journal 2000; 47: 363–369.
  • Jalali-Heravi M, Khandar AA, Sheikshoaie I. A theoretical investigation of the structure, electronic properties and second-order nonlinearity of some azo Schiff base ligands and their monoanions Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 1999; 55: 2537–2544.
  • Karakaş A, Elmalı A, Ünver H, Svoboda I. Nonlinear optical properties of some derivatives of salicylaldimine-based ligands. Journal of Molecular Structure 2004; 702: 103–110.
  • Sıdır YG, Sıdır I, Berber H, Türkoğlu G. Solvatochromic behavior and electronic structure of some symmetric 2-aminophenol Schiff base derivatives. Journal of Molecular Liquids 2014; 199: 57–66.
  • Sıdır YG, Sıdır I, Berber H, Türkoğlu G. Solvatochromism and electronic structure of some symmetric Schiff base derivatives. Journal of Molecular Liquids 2015; 204: 33–38.
  • Sıdır İ, Sıdır YG, Berber H, Demiray F. Emerging ground and excited state dipolemoments and external electric field effect on electronic structure. A solvatochromism and theoretical study on 2- ((phenylimino)methyl)phenol derivatives. Journal of Molecular Liquids 2015; 206: 56–67.
  • Sprung MM. A summary of the reaction of aldehydes with amines. Chemical Reviews 1940; 26: 297–334.
  • Gedye R, Smith F, Westaway K, Ali H, Baldisera L, Laberge L, Roussel J. The use of microwave ovens for rapid organic synthesis. Tetrahedron Letters 1986; 27(3): 279-282.
  • Giguere RJ, Bray, TL, Duncan SM, Majetich G. (1986). Application of commercial microwave ovens to organic synthesis. Tetrahedron Letters 1986; 27(41): 4945-4598.
  • Wade LG. Organic Chemistry. New York, Wiley, 1999.
  • Aghayan MM, Ghassemzadeh M, Hoseini M, Bolourtchian M. Microwave assisted synthesis of the tetradentate Schiff bases under solvent free-and catalyst free condition. Synthetic Communications 2003; 33: 521-525.
  • Lamiri M, Bougrin K, Daou B, Souflaoui M, Nicolas E, Giralt E. Microwaves assited solvent free regiospecific synthesis of 5-alkylidene and 5-arylidene hydantoins. Synthetic Communications 2006; 36: 1575–1584.
  • Aghera VK, Ghumara RY, Parsania PH. Microwave assisted and classical synthesis of symmetric double Schiff bases of 1,1-bis(4-mino3-methylphenyl)cyclohexane and their antimcrobial asay. Journal of Scientific Industrial Research 2015; 74: 43-47.
  • Loupy A, Petit A, Hamelin I, Texier-Boullet F, Jacquault P, Mathe D. New solvent free organic synthesis using focused microwaves. Synthesis 1998; 1213–1234.
  • Varma RS. Solvent free organic syntheses using supported reagent and microwave irradiation. Green Chemistry 1999; 1: 43–55.
  • Lidström P, Tiemey J, Wathey B, Westman J. Microwave assisted organic synthesis-a review. Tetrahedron 2001; 57: 9225-9283.
  • Ayoubi SA-E, Texier-Boullet F, Hamelin J. Minute synthesis of electrophilic alkenes under microwave irridation. Synthesis 1994; 258-260.
  • Bose DS, Jayalakshmi BJ. Reagents for organic synthesis: Use of organostannyl oxides as catalytic neutral agents in the preparation of nitriles from primary amides under microwave irradiation. Journal of Organic Chemistry 1999; 64 (5): 1713-1714.
  • Schwartz JB. Optimization techniques in pharmaceutical formulation and processing. In: Banker, editors. Modern Pharmaceutics. 4th ed. Marcel Dekker, New York, 2000. pp. 803-828.
  • Somani R, Pawar S, Nikam S, Shirodkar P, Kadam V. Microwave assisted synthesis and antimicrobial activity of some Schiff’s bases. International Journal of ChemTech Research 2010; 2(2): 860-864.
  • Yang H, Sun W, Li Z, Wang L. Solvent-free syntheses of salicylaldimines assisted by microwave irradiation. Synthetic Communications 2002; 32(15): 2395–2402.
  • Yang Z, Sun P. Compare of three ways of synthesis of simple Schiff base. Molbank 2006; M514: 1-3. [49] Zhang Y, Guo ZJ, You XZ. Hydrolysis Theory for Cisplatin and Its Analogues Based on Density Functional Studies. Journal of American Chemical Society 2001; 123: 9378–9387.
  • Tanak H, Ağar A, Yavuz M. Experimental and quantum chemical calculational studies on 2-[(4- Fluorophenylimino)methyl]-3,5-dimethoxyphenol. Journal of Molecular Modeling 2010; 16: 577-587. [51] Albayrak Ç, Kosar B, Odabaşoğlu M, Büyükgüngör O. Molecular and Computational Structure Characterizations of (E)-2-Ethoxy-6-[(4-fluorophenylimino)methyl]phenol. Journal of the Iranian Chemical Society 2011; 8(3): 674-686.
  • Khalaji AD, Mighani H, Gotoh K, Ishida H. Synthesis, Characterization, Structure, Ab Initio and DFT Calculations of 2-Amino-N-(3-phenylprop-2-enylidene)aniline. Journal of Chemical Crystallography 2011; 41: 1154–1157.
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There are 60 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Emel Ermiş

Publication Date April 25, 2016
Published in Issue Year 2016 Volume: 17 Issue: 1

Cite

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 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. June 2016;17(1):79-95. doi:10.18038/btda.70064
Chicago 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, no. 1 (June 2016): 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 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, 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 2016), 79-95. https://doi.org/10.18038/btda.70064.
JAMA 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, 2016, pp. 79-95, doi:10.18038/btda.70064.
Vancouver 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.