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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

Year 2015, Volume: 16 Issue: 1, 81 - 96, 28.05.2015

Emel Ermiş , Halil Berber

https://doi.org/10.18038/btd-a.95222

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

Keywords

3-Allylsalicylaldehyde o-Dianisidine Microwave-irradiation method Tautomeric equilibria DFT

References

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2-ALLİL-6,6'-[(3,3'-DİMETOKSİ[1,1'-BİFENİL]-4,4'- DİYİL)BİS(NİTRİLOMETİLİDEN)]BİS-FENOLÜN MİKRODALGA ve GELENEKSEL ISITMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU ve TAUTOMERİK ÖZELLİKLERİNİN DENEYSEL ve TEORİK OLARAK İNCELENMESİ

Year 2015, Volume: 16 Issue: 1, 81 - 96, 28.05.2015

Emel Ermiş , Halil Berber

https://doi.org/10.18038/btd-a.95222

Abstract

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.

Keywords

: 3-All lsal s laldeh t o-D an s d n M krodalga-ışınlama yöntem Tautomer k denge DFT

References

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  • Aghera, V. K., Ghumara, R.Y., ve Parsania, P. H. (2015). 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 74, 43-47.
  • Ahmed, I.S., Kassem, M.A. (2010). Synthesis, Solvatochromaticity and Bioactivities of Some Transition Metal Complexes with 2- (R-benzylideneamino)-pyridin-3-ol Schiff Base Derivatives. Spectrochimica Acta Part A 77, 359–366.
  • Annaraj, B., Pan, S., Neelakantan, M. A., Chattaraj, P. K. (2014). DFT Study On The Ground State and Excited State İntramolecular Proton Transfer of Propargyl Arm Containing Schiff Bases in Solution and Gas Phases. Computational and Theoretical Chemistry 1028, 19-26.
  • Ayoubi, S. A.-E., Texier-Boullet, F., Hamelin, J. (1994). Minute Synthesis of Electrophilic Alkenes under Microwave Irridation. Synthesis 258-260. Bellamy, L. J. (1966). Infrared Spectra of Complex Molecules, Wiley, New York.
  • Bilge, S., Kılıç, Z., Hayvalı, Z., Hökelek, T. ve Safran, S. (2009). Intramolecular Hydrogen Bonding and Tautomerism in Schiff Bases: Part VI. Syntheses and Structural Investigation of Salicylaldimine and Naphthaldimine Derivatives. Journal of Chemical Sciences 121 (6), 989–1001
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  • Devaraj, S., Tsui, Y., Chiang, C., Yen, Y. (2012). A New Dual Functional Sensor: Highly Selective Colorimetric Chemosensor for Fe3+ and Fluorescent Sensor for Mg2+ . Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96, 594–599.
  • Dürr, H. ve Bouas-Laurent, H. (1990). Photochromism: Molecular and Systems (Amsterdam: Elsevier).
  • Eshtiagh-Hosseini, H., Beyramabadi, S. A., Morsali, A., Mirzaei, M., Chegini, H., Elahi, M., Naseri, M. A. (2014). Synthesis, Characterization and Intramolecular Proton Transfer of 3,30-dihydroxy-4,40-[5-methyl- 1,3-phenylenebis(nitrilomethylidyne)]-bisphenol. Journal of Molecular Structure 1072, 187–194.
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  • Hadjoudis, E., Vitterakisp, M., Mavridis, I. M. (1987). Photochromism and Thermochromism of Schiff Bases in the Solid State and in Rigid Glasses. Tetrahedron 43, 1345-1360.
  • Hayvalı, Z., Hayvalı M., Kılıç, Z., Hökelek, T. and Weber, E. (2003). New Benzo-15- Crown-5 Ethers Featuring Salicylic Schiff Base Substitutions–Synthesis, Complexes and Structural Study. Journal of InclusionPhenomena and Macrocyclic Chemistry 45: 285–294.
  • Higelin, D. ve Sixl, H. (1983). Spectroscopic Studies of The Photochromism of N- Salicylideneaniline Mixed Crystals and Glasses. Chemical Physics 77, 391-400.
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  • Lamiri, M., Bougrin, K., Daou, B., Souflaoui, M., Nicolas, E., Giralt, E. (2006). Microwaves assited solvent free regiospecific synthesis of 5-alkylidene and 5-arylidene hydantoins. Synthetic Communications 36, 1575–1584.
  • Layer, R.W. (1963). The chemistry of imines. Chemical Reviews 63, 489–510. Lidström, P., Tiemey, J., Wathey, B. ve Westman, J. (2001). Microwave assisted organic synthesis-a review. Tetrahedron 57, 9225-9283.
  • Loupy, A., Petit, A., Hamelin, I., Texier-Boullet, F., Jacquault, P., Mathe, D. (1998). New solvent free organic synthesis using focused microwaves. Synthesis 1213–1234.
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There are 49 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Emel Ermiş

Halil Berber

Publication Date May 28, 2015
Published in Issue Year 2015 Volume: 16 Issue: 1

Cite

APA Ermiş, E., & Berber, H. (2015). 2-ALLİL-6,6’-[(3,3’-DİMETOKSİ[1,1’-BİFENİL]-4,4’- DİYİL)BİS(NİTRİLOMETİLİDEN)]BİS-FENOLÜN MİKRODALGA ve GELENEKSEL ISITMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU ve TAUTOMERİK ÖZELLİKLERİNİN DENEYSEL ve TEORİK OLARAK İNCELENMESİ. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 16(1), 81-96. https://doi.org/10.18038/btd-a.95222
AMA Ermiş E, Berber H. 2-ALLİL-6,6’-[(3,3’-DİMETOKSİ[1,1’-BİFENİL]-4,4’- DİYİL)BİS(NİTRİLOMETİLİDEN)]BİS-FENOLÜN MİKRODALGA ve GELENEKSEL ISITMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU ve TAUTOMERİK ÖZELLİKLERİNİN DENEYSEL ve TEORİK OLARAK İNCELENMESİ. AUJST-A. August 2015;16(1):81-96. doi:10.18038/btd-a.95222
Chicago Ermiş, Emel, and Halil Berber. “2-ALLİL-6,6’-[(3,3’-DİMETOKSİ[1,1’-BİFENİL]-4,4’- DİYİL)BİS(NİTRİLOMETİLİDEN)]BİS-FENOLÜN MİKRODALGA Ve GELENEKSEL ISITMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU Ve TAUTOMERİK ÖZELLİKLERİNİN DENEYSEL Ve TEORİK OLARAK İNCELENMESİ”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 16, no. 1 (August 2015): 81-96. https://doi.org/10.18038/btd-a.95222.
EndNote Ermiş E, Berber H (August 1, 2015) 2-ALLİL-6,6’-[(3,3’-DİMETOKSİ[1,1’-BİFENİL]-4,4’- DİYİL)BİS(NİTRİLOMETİLİDEN)]BİS-FENOLÜN MİKRODALGA ve GELENEKSEL ISITMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU ve TAUTOMERİK ÖZELLİKLERİNİN DENEYSEL ve TEORİK OLARAK İNCELENMESİ. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 16 1 81–96.
IEEE E. Ermiş and H. Berber, “2-ALLİL-6,6’-[(3,3’-DİMETOKSİ[1,1’-BİFENİL]-4,4’- DİYİL)BİS(NİTRİLOMETİLİDEN)]BİS-FENOLÜN MİKRODALGA ve GELENEKSEL ISITMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU ve TAUTOMERİK ÖZELLİKLERİNİN DENEYSEL ve TEORİK OLARAK İNCELENMESİ”, AUJST-A, vol. 16, no. 1, pp. 81–96, 2015, doi: 10.18038/btd-a.95222.
ISNAD Ermiş, Emel - Berber, Halil. “2-ALLİL-6,6’-[(3,3’-DİMETOKSİ[1,1’-BİFENİL]-4,4’- DİYİL)BİS(NİTRİLOMETİLİDEN)]BİS-FENOLÜN MİKRODALGA Ve GELENEKSEL ISITMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU Ve TAUTOMERİK ÖZELLİKLERİNİN DENEYSEL Ve TEORİK OLARAK İNCELENMESİ”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 16/1 (August 2015), 81-96. https://doi.org/10.18038/btd-a.95222.
JAMA Ermiş E, Berber H. 2-ALLİL-6,6’-[(3,3’-DİMETOKSİ[1,1’-BİFENİL]-4,4’- DİYİL)BİS(NİTRİLOMETİLİDEN)]BİS-FENOLÜN MİKRODALGA ve GELENEKSEL ISITMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU ve TAUTOMERİK ÖZELLİKLERİNİN DENEYSEL ve TEORİK OLARAK İNCELENMESİ. AUJST-A. 2015;16:81–96.
MLA Ermiş, Emel and Halil Berber. “2-ALLİL-6,6’-[(3,3’-DİMETOKSİ[1,1’-BİFENİL]-4,4’- DİYİL)BİS(NİTRİLOMETİLİDEN)]BİS-FENOLÜN MİKRODALGA Ve GELENEKSEL ISITMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU Ve TAUTOMERİK ÖZELLİKLERİNİN DENEYSEL Ve TEORİK OLARAK İNCELENMESİ”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, vol. 16, no. 1, 2015, pp. 81-96, doi:10.18038/btd-a.95222.
Vancouver Ermiş E, Berber H. 2-ALLİL-6,6’-[(3,3’-DİMETOKSİ[1,1’-BİFENİL]-4,4’- DİYİL)BİS(NİTRİLOMETİLİDEN)]BİS-FENOLÜN MİKRODALGA ve GELENEKSEL ISITMA YOLUYLA SENTEZİ, YAPI KARAKTERİZASYONU ve TAUTOMERİK ÖZELLİKLERİNİN DENEYSEL ve TEORİK OLARAK İNCELENMESİ. AUJST-A. 2015;16(1):81-96.
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