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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

Yıl 2015, Cilt: 16 Sayı: 1, 81 - 96, 28.05.2015

Emel Ermiş Halil Berber

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

Öz

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

Anahtar Kelimeler

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

Kaynakça

  • 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.
  • 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
  • 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.
  • 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.
  • 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.
  • Demircioğlu, Z., Albayrak, Ç., Büyükgüngör, O. (2014b). Experimental (X-ray, FT-IR and UV–vis spectra) and Theoretical Methods (DFT study) of (E)-3-methoxy-2-[(ptolylimino)methyl]phenol. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 128, 748–758.
  • 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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  • Giguere, R. J., Bray, T. L., Duncan, S. M., Majetich, G. (1986). Application of commercial microwave ovens to organic synthesis. Tetrahedron Letters 27 (41), 4945-4598.
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  • 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.
  • Hökelek, T., Gündüz, N., Hayvalı, Z. ve Kılıç, Z. (1995). Schiff bases and their complexes with metal ions. I. 2-Hydroxy-N-n-propyl-1- naphthaldimine (1) and Bis(2-hydroxy-kO- N-n-propyl-1-naphthaldiminato- kN)nickel(II) (2). Acta Crystallographica Section C C51, 880-884.
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  • Jayabharathi, J., Thanikachalam, V., Vennila, M., Jayamoorthy, K. (2012). Physico-chemical Studies of New Luminescent Chemosensor for Cu2+ . Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96, 677–683.
  • Kessisoglu, D. P., Raptopoulou, C. P., Bakalbassis, E. G., Terzis, A. ve Mrozinski, J. (1992). Molybdenum(VI)-Copper(II) Schiff-Base Complexes Having Cu2Mo2O4 Cubane-like Cores. Synthesis, Crystal Structure and Magnetic Properties of [Cu2Mo2O4(SALADHP)2(MeO)2. 2CH3CN]n [H3SALADHP = 1,3- Dihydroxy-2-methyl-2- (salicylideneamino)propane]. Inorganic Chemistry 31, 4339-4345.
  • Kim, S., Noh, J. Y., Kim, K. Y., Kim, J. H., Kang, H. K., Nam, S., Kim, S. H., Park, S., Kim, C. ve Kim, J. (2012). Salicylimine-Based Fluorescent Chemosensor for Aluminum Ions and Application to Bioimaging. Inorganic Chemistry 51, 3597−3602.
  • 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.
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  • 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.
  • Ogawa, K., Harada, J. (2003). Aggregation controlled proton tautomerization in salicylideneanilines. Journal of Molecular Structure 647, 211–216.
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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

Yıl 2015, Cilt: 16 Sayı: 1, 81 - 96, 28.05.2015

Emel Ermiş Halil Berber

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

Öz

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.

Anahtar Kelimeler

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

Kaynakça

  • 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.
  • 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
  • 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.
  • 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.
  • 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.
  • Demircioğlu, Z., Albayrak, Ç., Büyükgüngör, O. (2014b). Experimental (X-ray, FT-IR and UV–vis spectra) and Theoretical Methods (DFT study) of (E)-3-methoxy-2-[(ptolylimino)methyl]phenol. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 128, 748–758.
  • 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.
  • Gaussian 09, (2009). Revision B.01. M.J. Frisch. G.W. Trucks. H.B. Schlegel. G.E. Scuseria. M.A. Robb. J.R. Cheeseman. G. Scalmani. V. Barone. B. Mennucci. G.A. Petersson. H. Nakatsuji. M. Caricato. X. Li. H.P. Hratchian. A.F. Izmaylov. J. Bloino. G. Zheng. J.L. Sonnenberg. M. Hada. M. Ehara. K. Toyota. R. Fukuda. J. Hasegawa. M. Ishida. T. Nakajima. Y. Honda. O. Kitao. H. Nakai. T. Vreven. J.A. Montgomery Jr. J.E. Peralta. F. Ogliaro. M. Bearpark. J.J. Heyd. E. Brothers. K.N. Kudin. V.N. Staroverov. R. Kobayashi. J. Normand. K. Raghavachari. A. Rendell. J.C. Burant. S.S. Iyengar. J. Tomasi. M. Cossi. N. Rega. J.M. Millam. M. Klene. J.E. Knox. J.B. Cross. V. Bakken. C. Adamo. J. Jaramillo. R. Gomperts. R.E. Stratmann. O. Yazyev. A.J. Austin. R. Cammi. C. Pomelli. J.W. Ochterski. R.L. Martin. K. Morokuma. V.G. Zakrzewski. G.A. Voth. P. Salvador. J.J. Dannenberg. S. Dapprich. A.D. Daniels. O. Farkas. J.B. Foresman. J.V. Ortiz. J. Cioslowski. D.J. Fox. Gaussian Inc.. Wallingford. CT.
  • Gedye, R., Smith, F., Westaway, K., Ali, H., Baldisera, L., Laberge, L., Roussel, J. (1986). The use of Microwave Ovens for Rapid Organic Synthesis. Tetrahedron Letters 27 (3), 279-282.
  • Giguere, R. J., Bray, T. L., Duncan, S. M., Majetich, G. (1986). Application of commercial microwave ovens to organic synthesis. Tetrahedron Letters 27 (41), 4945-4598.
  • Hadjoudis, E. (1981). Photochromism and Thermochromism of N-salicylideneanilines and N-salicylideneaminopyridines. Journal of Photochemistry 17, 355-363.
  • 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.
  • Hökelek, T., Gündüz, N., Hayvalı, Z. ve Kılıç, Z. (1995). Schiff bases and their complexes with metal ions. I. 2-Hydroxy-N-n-propyl-1- naphthaldimine (1) and Bis(2-hydroxy-kO- N-n-propyl-1-naphthaldiminato- kN)nickel(II) (2). Acta Crystallographica Section C C51, 880-884.
  • Hökelek, T., Bilge, S., Demiriz, Ş., Özgüç, B., Kılıç, Z. (2004). 1,3-[Bis(N-2- oxyphenylsalicylydene)]propane. Acta Crystallographica Section C C60, 803-805. https://www.organicdivision.org/orig/organic_so lvents.html.
  • Jayabharathi, J., Thanikachalam, V., Vennila, M., Jayamoorthy, K. (2012). Physico-chemical Studies of New Luminescent Chemosensor for Cu2+ . Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96, 677–683.
  • Kessisoglu, D. P., Raptopoulou, C. P., Bakalbassis, E. G., Terzis, A. ve Mrozinski, J. (1992). Molybdenum(VI)-Copper(II) Schiff-Base Complexes Having Cu2Mo2O4 Cubane-like Cores. Synthesis, Crystal Structure and Magnetic Properties of [Cu2Mo2O4(SALADHP)2(MeO)2. 2CH3CN]n [H3SALADHP = 1,3- Dihydroxy-2-methyl-2- (salicylideneamino)propane]. Inorganic Chemistry 31, 4339-4345.
  • Kim, S., Noh, J. Y., Kim, K. Y., Kim, J. H., Kang, H. K., Nam, S., Kim, S. H., Park, S., Kim, C. ve Kim, J. (2012). Salicylimine-Based Fluorescent Chemosensor for Aluminum Ions and Application to Bioimaging. Inorganic Chemistry 51, 3597−3602.
  • 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.
  • Ogawa, K., Harada, J. (2003). Aggregation controlled proton tautomerization in salicylideneanilines. Journal of Molecular Structure 647, 211–216.
  • Ohshima, A., Momotake, A., Arai, T. (2004). Photochromism, Thermochromism, and Solvatochromism of Naphthalene-based Analogues of Salicylideneaniline in solution. Journal of Photochemistry and Photobiology A: Chemistry 162, 473–479.
  • Pandey, A., Dewangan D., Verma, S., Mishra, A., Dubey, R. D. (2011). Synthesis of Schiff bases of 2-amino-5-aryl-1,3,4-thiadiazole and Its Analgesic, Anti-Inflammatory,Anti- Bacterial and Anti-Tubercular Activity. International Journal of ChemTech Research 3(1), 178-184.
  • Panneerselvam, P., Reddy,R. S., Murali, K., ve Kumar, N. R. (2010). Synthesis, Analgesic, Anti-İnflammatory and Antimicrobial Activities of Some Novel Schiff’s Bases of 5-subsituted Isatin. Der Pharma Chemica 2(1), 28-37.
  • Percino, M. J., Cerón, M., Castro, M. E., Ramírez, R., Soriano, G., Chapela, V. M. (2015). (E)-2-[(2- hydroxybenzylidene)amino]phenylarsonic acid Schiff base: Synthesis, Characterization and Theoretical Studies. Journal of Molecular Structure 1081, 193–200.
  • Schiff, H. (1869). Untersuchungen über salicinderivate. Annalen der Chemie 150, 193-200.
  • Schwartz, J. B. (2000). Optimization Techniques in Pharmaceutical Formulation and Processing in Banker. 4th Ed. Modern Pharmaceutics, Marcel Dekker, New York, 803-828.
  • Sharma, V., Mehta D. K., Bala S., Das R. (2013). A review on biologically active Schiff base derivatives. International Journal of Universal Pharmacy and Bio Sciences 2(4), 241-257.
  • Sen, S., De, B., Panday, L., Easwari, T. S., Nagarajan, A. S. (2010). Pharmacological Study of Some Newly Synthesized Furan Derivatives. Der Pharma Chemica 2(3), 74- 82.
  • Sıdır, Y. G., Sıdır, I., Berber, H., Türkoğlu, G. (2014). Solvatochromic Behavior and Electronic Structure of Some Symmetric 2- Aminophenol Schiff Base Derivatives. Journal of Molecular Liquids 199, 57–66.
  • Somani, R., Pawar, S., Nikam, S., Shirodkar, P., Kadam, V. (2010). Microwave Assisted Synthesis and Antimicrobial Activity of Some Schiff’s Bases. International Journal of ChemTech Research 2 (2), 860-864.
  • Sprung, M. M. (1940). A summary of The Reaction of Aldehydes with Amines. Chemical Reviews 26, 297–334.
  • Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D., Lectka, T. (2002). The Development of The First Catalyzed Reaction of Ketenes and Imines:  Catalytic, Asymmetric Synthesis of β-Lactams. Journal of the American Chemical Society 124, 6626–6635.
  • Varma, R. S. (1999). Solvent Free Organic Syntheses using Supported Reagent and Microwave İrradiation. Green Chemistry 1, 43–55.
  • Yang, L., Zhu, W., Fang, M., Zhang, Q., Li, C. (2013). A New Carbazole-Based Schiff- Base As Fluorescentchemosensor for Selective Detection of Fe3+ and Cu 2+ . Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 109, 186–192.
  • Yang, Z., Sun, P. (2006). Compare of Three Ways of Synthesis of Simple Schiff Base. Molbank M514, 1-3.
  • Yang, H., Sun, W., Li, Z. ve Wang, L. (2002). Solvent-free Syntheses of Salicylaldimines Assisted by Microwave Irradiation. Synthetic Communications 32 (15), 2395– 2402.
  • Ye, H., Ge, F., Zhou, Y., Liu, J., Zhao, B. (2013). A new Schiff base fluorescent probe for imaging Cu2+ in living cells. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 112, 132–138.
  • Yıldız, M., Karpuz, Ö., Zeyrek, C. T., Boyacioglu, B., Dal, H., Demir, N., Yıldırım, N., Unver, H. (2015). Synthesis, Biological Activity, DNA Binding and Anion Sensors, Molecular Structure and Quantum Chemical Studies of A Novel Bidentate Schiff Base Derived from 3,5- bis(triflouromethyl)aniline and salicylaldehyde. Journal of Molecular Structure 1094,148-160.
  • Zhao, J., Zhao, B., Liu, J., Xu, W. ve Wang, Z. (2001). Spectroscopy study on the photochromism of Schiff bases N,N′- bis(salicylidene)-1,2-diaminoethane and N,N′-bis(salicylidene)-1,6-hexanediamine. Spectrochimica Acta A 57 (1), 149-154
Toplam 49 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Araştırma Makalesi
Yazarlar

Emel Ermiş

Halil Berber

Yayımlanma Tarihi 28 Mayıs 2015
Yayımlandığı Sayı Yıl 2015 Cilt: 16 Sayı: 1

Kaynak Göster

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. AUBTD-A. Ağustos 2015;16(1):81-96. doi:10.18038/btd-a.95222
Chicago Ermiş, Emel, ve 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, sy. 1 (Ağustos 2015): 81-96. https://doi.org/10.18038/btd-a.95222.
EndNote Ermiş E, Berber H (01 Ağustos 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 ve 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”, AUBTD-A, c. 16, sy. 1, ss. 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 (Ağustos 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. AUBTD-A. 2015;16:81–96.
MLA Ermiş, Emel ve 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, c. 16, sy. 1, 2015, ss. 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. AUBTD-A. 2015;16(1):81-96.
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