SavedAdd your journal

Journals / Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering / 2015 / Cilt: 16 - Sayı: 1

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

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

Emel ERMİŞ
Halil BERBER
Pages
81–96
Publication Date
2015-05-28
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

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

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

📌 3 Key Takeaways

🎯
Objective & Hypothesis: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.
📊
Key Findings & Data:H-Ntautomers) in various organic solvents were studied using UV-visible region spectrophotometric methodand keto-amine percentages were calculated.
💡
Conclusion & Impact: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
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:: 3-All lsal s laldeh t · o-D an s d n · M krodalga-ışınlama yöntem

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

Özet

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.

🔖

Cite This Article

ERMİŞ, E., BERBER, H. (2015). 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. Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering, Cilt: 16 - Sayı: 1, 81–96. https://ajindex.com/articles/196933

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (11)

  1. Aghayan, M. M., Ghassemzadeh, M., Hoseini, M. & Bolourtchian, M. (2003). Microwave Assisted Synthesis of The Tetradentate Schiff Bases under Solvent Free-and Catalyst free Condition. Synthetic Communications 33, 521-525.
  2. 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.
  3. Ahmed, I.S., Kassem, M.A. (2010).
  4. 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.
  5. 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.
  6. Ayoubi, S. A.-E., Texier-Boullet, F., Hamelin, J. (1994). Minute Synthesis of Electrophilic Alkenes under Microwave Irridation. Synthesis 258-260.
  7. 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
  8. Bose, D. S., Jayalakshmi, B. J. (1999). 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 64 (5), 1713-1714.
  9. Cohen, M. D., Schmidt, G. M. J., Flavian, S. (1964). Topochemistry. Part VI. Experiments on photochromy and thermochromy of crystalline anils of salicylaldehydes. Journal of the Chemical Society 2041–2051.
  10. Corsaro, A.; Chiacchio, U.; Pistara, V. ve Romeo, G. (2004). Microwave-assisted chemistry of carbohydrates. Current Organic Chemistry 8(6), 511-538. CS ChemOffice Pro for Microsoft Windows. Demircioğlu, Z., Albayrak, Ç., Büyükgüngör, O. (2014a). Theoretical and experimental investigation of (E)-2-([3,4- dimethylphenyl)imino]methyl)-3- methoxyphenol: Enol–keto tautomerism, spectroscopic properties, NLO, NBO and NPA analysis. Journal of Molecular Structure 1065-1066, 210–222.
  11. Demircioğlu, Z., Albayrak, Ç., Büyükgüngör, O. (2014b). Experimental (X-ray, FT