Research Article
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Experimental and Theoretical Approaches for the Characterization of the Novel ((Ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(4,1-phenylene) Diacrylate Molecule

Year 2020, Volume: 9 Issue: 2, 17 - 31, 15.09.2020

Uğur Soykan Sedat Çetin Gurcan Yildirim

Abstract

This multidisciplinary study deals with not only the synthesis of the novel ((ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(4,1-phenylene) diacrylate (ABCEDA) molecule but also the experimental and theoretical (with DFT and HF methods) characterization of the title compound for the first time. The experimental results obtained from FT-IR and 1H-NMR verified that the title novel molecule was synthesized without any impurities and the reaction yield was about 68 wt%. DSC melting temperature and crystallization temperature belonging to the studied molecule were found to be 335 °C and 226 °C, respectively. As for molecular geometric properties, there was little deviation on the calculated bond angles and bond lengths of the compound. Both bond angles and bond lengths computed from DFT method were slightly greater than the results obtained from the HF method due to the fact that the electron correlation coefficients were taken into account in DFT method. The optical band gap energy of the compound was computed to be about 0.3904 a.u. (10.6233 eV), conforming that the molecule had low electronic donor ability. Moreover, MEP analysis showed that the molecule possessed the possible sites for the electrophilic and nucleophilic attacks. Furthermore, the negative ESP spread over mostly on the oxygen atom whereas the positive ESP was located on the rest of the molecule.

Keywords

ethane-1-2-diylbis(azanediyl))bis(carbonyl))bis(4-1-phenylene) diacrylate DFT and HF methods HOMO-LUMO MEP and ESP maps

Supporting Institution

Bolu Abant Izzet Baysal University,

Project Number

BAP-2014.03.03.686.

Thanks

This work was supported by BAIBU research fund grand no. BAP-2014.03.03.686. Furthermore, the authors especially thanks to Scientific, Industrial and Technological application and Research Center (BETUM) and Innovative Food Technologies Development Application and Research Center (YENIGIDAM) for valuable supports.

References

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  • Benhamou, M., and Chahid, M. (2008). Field-theoretical Renormalization-Group approach to critical dynamics of crosslinked polymer blends. European Physical Journal E, 27(1), 57-62.
  • Benmouna, F., Maschke, U., Coqueret, X., and Benmouna, M. (2001). Theoretical phase behavior of crosslinked polymers and liquid crystals. Macromolecular Theory and Simulations, 10(1), 63-70.
  • Buyukuslu, H., Akdogan, M., Yildirim, G., and Parlak, C. (2010). Ab initio Hartree-Fock and density functional theory study on characterization of 3-(5-methylthiazol-2-yldiazenyl)-2-phenyl-1H-indole. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 75(4), 1362-1369.
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  • Gao, C., Yan, T., Dai, K. R., and Wan, Y. Z. (2012). Immobilization of gelatin onto natural nanofibers for tissue engineering scaffold applications without utilization of any crosslinking agent. Cellulose, 19(3), 761-768.
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  • Koca, M., Yildirim, G., Kirilmis, C., and Karaboga, F. (2012). Density Functional Theory Study on the Identification of Pd(Me-Xanthate)(2). Arabian Journal for Science and Engineering, 37(5), 1283-1291.
  • Lenhart, J. L., and Cole, P. J. (2006). Adhesion properties of lightly crosslinked solvent-swollen polymer gels. Journal of Adhesion, 82(10), 945-971.
  • Lewis, D. F. V., Ioannides, C., and Parke, D. V. (1994). Interaction of a Series of Nitriles with the Alcohol-Inducible Isoform of P450 - Computer-Analysis of Structure-Activity-Relationships. Xenobiotica, 24(5), 401-408.
  • Luo, D., Li, Y., and Yang, M. J. (2011). Preparation and Characterization of Novel Crosslinked Poly[glycidyl methacrylate-poly(ethylene glycol) methyl ether methacrylate] as Gel Polymer Electrolytes. Journal of Applied Polymer Science, 120(5), 2979-2984.
  • Ma, X., Jiao, J. M., Yang, J., Huang, X. B., Cheng, Y. X., and Zhu, C. J. (2012). Large stokes shift chiral polymers containing (R,R)-salen-based binuclear boron complex: Synthesis, characterization, and fluorescence properties. Polymer, 53(18), 3894-3899.
  • Margel, S., Nov, E., and Fisher, I. (1991). Polychloromethylstyrene Microspheres - Synthesis and Characterization. Journal of Polymer Science Part a-Polymer Chemistry, 29(3), 347-355.
  • Martinez, A., Blanco, M. D., Davidenko, N., and Cameron, R. E. (2015). Tailoring chitosan/collagen scaffolds for tissue engineering: Effect of composition and different crosslinking agents on scaffold properties. Carbohydrate Polymers, 132, 606-619.
  • Maryanski, M. J., Audet, C., and Gore, J. C. (1997). Effects of crosslinking and temperature on the dose response of a BANG polymer gel dosimeter. Physics in Medicine and Biology, 42(2), 303-311.
  • Montazer, M., and Jolaei, M. M. (2010). beta-Cyclodextrin Stabilized on Three-Dimensional Polyester Fabric with Different Crosslinking Agents. Journal of Applied Polymer Science, 116(1), 210-217.
  • Osada, Y., Gong, J. P., and Tanaka, Y. (2004). Polymer gels (Reprinted from Functional Monomers and Polymers, pg 497-528, 1997). Journal of Macromolecular Science-Polymer Reviews, C44(1), 87-112.
  • Ozdemir, N., Eren, B., Dincer, M., and Bekdemir, Y. (2010). Experimental and ab initio computational studies on 4-(1H-benzo[d]imidazol-2-yl)-N,N-dimethylaniline. Molecular Physics, 108(1), 13-24.
  • Park, K. Y., Jeong, W. W., and Suh, K. D. (2003). Monodisperse crosslinked microsphere polymer particles by dispersion copolymerization of glycidyl methacrylate and divinylbenzene. Journal of Macromolecular Science-Pure and Applied Chemistry, A40(6), 617-627.
  • Parlak, C., Akdogan, M., Yildirim, G., Karagoz, N., Budak, E., and Terzioglu, C. (2011). Density functional theory study on the identification of 3-[(2-morpholinoethylimino)methyl]benzene-1,2-diol. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 79(1), 263-271.
  • Pascal, J. A., Medidhi, K. R., Oyanader, M. A., Stretz, H. A., and Arce, P. E. (2019). Understanding Collaborative Effects between the Polymer Gel Structure and the Applied Electrical Field in Gel Electrophoresis Separation. International Journal of Polymer Science.
  • Philip, C. M., and Mathew, B. (2008). Design of EGDMA-crosslinked theophylline imprinted polymer with high specificity and selectivity. Journal of Macromolecular Science Part a-Pure and Applied Chemistry, 45(4), 335-343.
  • Pittman, C. U., Xu, X. M., Wang, L. C., and Toghiani, H. (2000). Mechanical and viscoelastic properties of semi-interpenetrating polymer networks of poly(vinyl chloride)/thermosetting resin blends. Polymer Engineering and Science, 40(6), 1405-1413.
  • Prasad, O., Sinha, L., Misra, N., Narayan, V., Kumar, N., and Pathak, J. (2010). Molecular structure and vibrational study on 2,3-dihydro-1H-indene and its derivative 1H-indene-1,3(2H)-dione by density functional theory calculations. Journal of Molecular Structure-Theochem, 940(1-3), 82-86.
  • Qian, G., Zhong, Z., Luo, M., Yu, D., Zhang, Z., Ma, D., and Wang, Z. Y. (2009). Synthesis and Application of Thiadiazoloquinoxaline-Containing Chromophores as Dopants for Efficient Near-Infrared Organic Light-Emitting Diodes. Journal of Physical Chemistry C, 113(4), 1589-1595.
  • Sert, Y., Gokce, H., Chandra, Mahendra, M., Srikantamurthy, N., and Cirak, C. (2019). Molecular docking and vibrational spectroscopy studies of (E)-N '-hydroxy-1,3-diphenyl-4,5-dihydro-1H-pyrazole-5-carboximidamide. Journal of Molecular Structure, 1184, 79-91.
  • Smolin, Y. Y., Janakiraman, S., Soroush, M., and Lau, K. K. S. (2017). Experimental and theoretical investigation of dye sensitized solar cells integrated with crosslinked poly(vinylpyrrolidone) polymer electrolyte using initiated chemical vapor deposition. Thin Solid Films, 635, 9-16.
  • Soykan, U., Cetin, S., Ozturk, B., Karaboga, F., Zalaoglu, Y., Dogruer, M., Terzioglu, C. (2013). Synthesis and characterization of p-benzophenoneoxycarbonylphenyl acrylate by means of experimental measurements and theoretical approaches, and bulk melt polymerization. Journal of Molecular Structure, 1049, 479-487.
  • Stankova, M., Jandera, P., and Hajek, T. (2013). Characterization of Prepared Monilithic Capillary Columns. Chemicke Listy, 107, S449-S451.
  • Stephens, P. J., Devlin, F. J., Chabalowski, C. F., and Frisch, M. J. (1994). Ab-Initio Calculation of Vibrational Absorption and Circular-Dichroism Spectra Using Density-Functional Force-Fields. Journal of Physical Chemistry, 98(45), 11623-11627.
  • Subashchandrabose, S., Saleem, H., Erdogdu, Y., Dereli, O., Thanikachalam, V., and Jayabharathi, J. (2012). Structural, vibrational and hyperpolarizability calculation of (E)-2-(2-hydroxybenzylideneamino)-3-methylbutanoic acid. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 86, 231-241.
  • Sun, Y. X., Hao, Q. L., Lu, L. D., Wang, X., and Yang, X. J. (2010). Vibrational spectroscopic study of o-, m- and p-hydroxybenzylideneaminoantipyrines. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 75(1), 203-211.
  • Tezer, N., and Karakus, N. (2009). Theoretical study on the ground state intramolecular proton transfer (IPT) and solvation effect in two Schiff bases formed by 2-aminopyridine with 2-hydroxy-1-naphthaldehyde and 2-hydroxy salicylaldehyde. Journal of Molecular Modeling, 15(3), 223-232.
  • Ucun, F., Guclu, V., and Saglam, A. (2008). Ab initio Hartree-Fock and density functional theory study on molecular structures, energies, and vibrational frequencies of conformations of 2-hydroxy-3-nitropyridine and 3-hydroxy-2-nitropyridine. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 70(3), 524-531.
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Year 2020, Volume: 9 Issue: 2, 17 - 31, 15.09.2020

Uğur Soykan Sedat Çetin Gurcan Yildirim

Abstract

Project Number

BAP-2014.03.03.686.

References

  • Abdelkader, A. F., and White, J. R. (2005). Curing characteristics and internal stresses in epoxy coatings: Effect of crosslinking agent. Journal of Materials Science, 40(8), 1843-1854.
  • Akyildiz, F., Alyar, S., Bilkan, M. T., and Alyar, H. (2018). Synthesis, characterization, spectroscopic properties, DFT calculations and antimicrobial activities of p-toluenesulfonamide,N,N'-1,3-propanediylbis(ptspr) and [Cu(II)(phenanthroline) (2)]ptspr. Journal of Molecular Structure, 1174, 160-170.
  • Arioglu, C., Tamer, O., Avci, D., and Atalay, Y. (2018). Optimized geometry, spectroscopic characterization and nonlinear optical properties of carbazole picrate: a density functional theory study. Indian Journal of Physics, 92(12), 1613-1621.
  • Bakhshi, A. K., and Rattan, P. (1998). Ab initio study of novel low-band-gap donor-acceptor polymers based on poly(cyclopentadienylene). Journal of the Chemical Society-Faraday Transactions, 94(18), 2823-2826.
  • Benhamou, M., and Chahid, M. (2008). Field-theoretical Renormalization-Group approach to critical dynamics of crosslinked polymer blends. European Physical Journal E, 27(1), 57-62.
  • Benmouna, F., Maschke, U., Coqueret, X., and Benmouna, M. (2001). Theoretical phase behavior of crosslinked polymers and liquid crystals. Macromolecular Theory and Simulations, 10(1), 63-70.
  • Buyukuslu, H., Akdogan, M., Yildirim, G., and Parlak, C. (2010). Ab initio Hartree-Fock and density functional theory study on characterization of 3-(5-methylthiazol-2-yldiazenyl)-2-phenyl-1H-indole. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 75(4), 1362-1369.
  • Cakir, I., Soykan, U., Cetin, S., Karaboga, F., Zalaoglu, Y., Dogruer, M., .Yildirim, G. (2014). Electrochemical and spectroscopic characteristics of p-acryloyloxybenzoyl chloride and p-acryloyloxybenzoic acid and antimicrobial activity of organic compounds. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 132, 502-513.
  • Ceylan, U., Tari, G. O., Gokce, H., and Agar, E. (2016). Spectroscopic (FT-IR and UV-Vis) and theoretical (HF and DFT) investigation of 2-Ethyl-N-[(5-nitrothiophene-2-yl)methylidene] aniline. Journal of Molecular Structure, 1110, 1-10.
  • Cirak, C., and Koc, N. (2012). Molecular structure and effects of intermolecular hydrogen bonding on the vibrational spectrum of trifluorothymine, an antitumor and antiviral agent. Journal of Molecular Modeling, 18(9), 4453-4464.
  • Cormack, P. A. G., and Elorza, A. Z. (2004). Molecularly imprinted polymers: synthesis and characterisation. Journal of Chromatography B-Analytical Technologies in the Biomedical and Life Sciences, 804(1), 173-182.
  • Durig, J. R., El-Defrawy, A. M., Ganguly, A., Panikar, S. S., and Soliman, M. S. (2011). Conformational Stability from Variable-Temperature Infrared Spectra of Xenon Solutions, r(0) Structural Parameters, and Vibrational Assignment of Pyrrolidine. Journal of Physical Chemistry A, 115(26), 7473-7483.
  • Elder, B. D., Mohan, A., and Athanasiou, K. A. (2011). Beneficial Effects of Exogenous Crosslinking Agents on Self-Assembled Tissue Engineered Cartilage Construct Biomechanical Properties. Journal of Mechanics in Medicine and Biology, 11(2), 433-443.
  • Gao, C., Yan, T., Dai, K. R., and Wan, Y. Z. (2012). Immobilization of gelatin onto natural nanofibers for tissue engineering scaffold applications without utilization of any crosslinking agent. Cellulose, 19(3), 761-768.
  • Gokce, H., and Bahceli, S. (2011). A study on quantum chemical calculations of 3-, 4-nitrobenzaldehyde oximes. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 79(5), 1783-1793.
  • Gomez, C. G., and Strumia, M. C. (2001). Synthesis of a triacrylate crosslinking agent and its use in the preparation of macroporous polymers. Polymer Bulletin, 47(3-4), 261-268.
  • Hatch, F. T., Lightstone, F. C., and Colvin, M. E. (2000). Quantitative structure-activity relationship of flavonoids for inhibition of heterocyclic amine mutagenicity. Environmental and Molecular Mutagenesis, 35(4), 279-299.
  • Hiremath, C. S., Kalkoti, G. B., and Aralakkanavar, M. K. (2009). Revised vibrational band assignments for the experimental IR and Raman spectra of 2,3,4-trifluorobenzonitrile based on ab initio, DFT and normal coordinate calculations. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 74(1), 200-204.
  • Iwakura, C., Furukawa, N., Ohnishi, T., Sakamoto, K., Nohara, S., and Inoue, H. (2001). Nickel/metal hydride cells using an alkaline polymer gel electrolyte based on potassium salt of crosslinked poly(acrylic acid). Electrochemistry, 69(9), 659-663.
  • Karaboga, F., Soykan, U., Dogruer, M., Ozturk, B., Yildirim, G., Cetin, S., and Terzioglu, C. (2013). Experimental and theoretical approaches for identification of p-benzophenoneoxycarbonylphenyl acrylate. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 113, 80-91.
  • Koca, M., Yildirim, G., Kirilmis, C., and Karaboga, F. (2012). Density Functional Theory Study on the Identification of Pd(Me-Xanthate)(2). Arabian Journal for Science and Engineering, 37(5), 1283-1291.
  • Lenhart, J. L., and Cole, P. J. (2006). Adhesion properties of lightly crosslinked solvent-swollen polymer gels. Journal of Adhesion, 82(10), 945-971.
  • Lewis, D. F. V., Ioannides, C., and Parke, D. V. (1994). Interaction of a Series of Nitriles with the Alcohol-Inducible Isoform of P450 - Computer-Analysis of Structure-Activity-Relationships. Xenobiotica, 24(5), 401-408.
  • Luo, D., Li, Y., and Yang, M. J. (2011). Preparation and Characterization of Novel Crosslinked Poly[glycidyl methacrylate-poly(ethylene glycol) methyl ether methacrylate] as Gel Polymer Electrolytes. Journal of Applied Polymer Science, 120(5), 2979-2984.
  • Ma, X., Jiao, J. M., Yang, J., Huang, X. B., Cheng, Y. X., and Zhu, C. J. (2012). Large stokes shift chiral polymers containing (R,R)-salen-based binuclear boron complex: Synthesis, characterization, and fluorescence properties. Polymer, 53(18), 3894-3899.
  • Margel, S., Nov, E., and Fisher, I. (1991). Polychloromethylstyrene Microspheres - Synthesis and Characterization. Journal of Polymer Science Part a-Polymer Chemistry, 29(3), 347-355.
  • Martinez, A., Blanco, M. D., Davidenko, N., and Cameron, R. E. (2015). Tailoring chitosan/collagen scaffolds for tissue engineering: Effect of composition and different crosslinking agents on scaffold properties. Carbohydrate Polymers, 132, 606-619.
  • Maryanski, M. J., Audet, C., and Gore, J. C. (1997). Effects of crosslinking and temperature on the dose response of a BANG polymer gel dosimeter. Physics in Medicine and Biology, 42(2), 303-311.
  • Montazer, M., and Jolaei, M. M. (2010). beta-Cyclodextrin Stabilized on Three-Dimensional Polyester Fabric with Different Crosslinking Agents. Journal of Applied Polymer Science, 116(1), 210-217.
  • Osada, Y., Gong, J. P., and Tanaka, Y. (2004). Polymer gels (Reprinted from Functional Monomers and Polymers, pg 497-528, 1997). Journal of Macromolecular Science-Polymer Reviews, C44(1), 87-112.
  • Ozdemir, N., Eren, B., Dincer, M., and Bekdemir, Y. (2010). Experimental and ab initio computational studies on 4-(1H-benzo[d]imidazol-2-yl)-N,N-dimethylaniline. Molecular Physics, 108(1), 13-24.
  • Park, K. Y., Jeong, W. W., and Suh, K. D. (2003). Monodisperse crosslinked microsphere polymer particles by dispersion copolymerization of glycidyl methacrylate and divinylbenzene. Journal of Macromolecular Science-Pure and Applied Chemistry, A40(6), 617-627.
  • Parlak, C., Akdogan, M., Yildirim, G., Karagoz, N., Budak, E., and Terzioglu, C. (2011). Density functional theory study on the identification of 3-[(2-morpholinoethylimino)methyl]benzene-1,2-diol. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 79(1), 263-271.
  • Pascal, J. A., Medidhi, K. R., Oyanader, M. A., Stretz, H. A., and Arce, P. E. (2019). Understanding Collaborative Effects between the Polymer Gel Structure and the Applied Electrical Field in Gel Electrophoresis Separation. International Journal of Polymer Science.
  • Philip, C. M., and Mathew, B. (2008). Design of EGDMA-crosslinked theophylline imprinted polymer with high specificity and selectivity. Journal of Macromolecular Science Part a-Pure and Applied Chemistry, 45(4), 335-343.
  • Pittman, C. U., Xu, X. M., Wang, L. C., and Toghiani, H. (2000). Mechanical and viscoelastic properties of semi-interpenetrating polymer networks of poly(vinyl chloride)/thermosetting resin blends. Polymer Engineering and Science, 40(6), 1405-1413.
  • Prasad, O., Sinha, L., Misra, N., Narayan, V., Kumar, N., and Pathak, J. (2010). Molecular structure and vibrational study on 2,3-dihydro-1H-indene and its derivative 1H-indene-1,3(2H)-dione by density functional theory calculations. Journal of Molecular Structure-Theochem, 940(1-3), 82-86.
  • Qian, G., Zhong, Z., Luo, M., Yu, D., Zhang, Z., Ma, D., and Wang, Z. Y. (2009). Synthesis and Application of Thiadiazoloquinoxaline-Containing Chromophores as Dopants for Efficient Near-Infrared Organic Light-Emitting Diodes. Journal of Physical Chemistry C, 113(4), 1589-1595.
  • Sert, Y., Gokce, H., Chandra, Mahendra, M., Srikantamurthy, N., and Cirak, C. (2019). Molecular docking and vibrational spectroscopy studies of (E)-N '-hydroxy-1,3-diphenyl-4,5-dihydro-1H-pyrazole-5-carboximidamide. Journal of Molecular Structure, 1184, 79-91.
  • Smolin, Y. Y., Janakiraman, S., Soroush, M., and Lau, K. K. S. (2017). Experimental and theoretical investigation of dye sensitized solar cells integrated with crosslinked poly(vinylpyrrolidone) polymer electrolyte using initiated chemical vapor deposition. Thin Solid Films, 635, 9-16.
  • Soykan, U., Cetin, S., Ozturk, B., Karaboga, F., Zalaoglu, Y., Dogruer, M., Terzioglu, C. (2013). Synthesis and characterization of p-benzophenoneoxycarbonylphenyl acrylate by means of experimental measurements and theoretical approaches, and bulk melt polymerization. Journal of Molecular Structure, 1049, 479-487.
  • Stankova, M., Jandera, P., and Hajek, T. (2013). Characterization of Prepared Monilithic Capillary Columns. Chemicke Listy, 107, S449-S451.
  • Stephens, P. J., Devlin, F. J., Chabalowski, C. F., and Frisch, M. J. (1994). Ab-Initio Calculation of Vibrational Absorption and Circular-Dichroism Spectra Using Density-Functional Force-Fields. Journal of Physical Chemistry, 98(45), 11623-11627.
  • Subashchandrabose, S., Saleem, H., Erdogdu, Y., Dereli, O., Thanikachalam, V., and Jayabharathi, J. (2012). Structural, vibrational and hyperpolarizability calculation of (E)-2-(2-hydroxybenzylideneamino)-3-methylbutanoic acid. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 86, 231-241.
  • Sun, Y. X., Hao, Q. L., Lu, L. D., Wang, X., and Yang, X. J. (2010). Vibrational spectroscopic study of o-, m- and p-hydroxybenzylideneaminoantipyrines. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 75(1), 203-211.
  • Tezer, N., and Karakus, N. (2009). Theoretical study on the ground state intramolecular proton transfer (IPT) and solvation effect in two Schiff bases formed by 2-aminopyridine with 2-hydroxy-1-naphthaldehyde and 2-hydroxy salicylaldehyde. Journal of Molecular Modeling, 15(3), 223-232.
  • Ucun, F., Guclu, V., and Saglam, A. (2008). Ab initio Hartree-Fock and density functional theory study on molecular structures, energies, and vibrational frequencies of conformations of 2-hydroxy-3-nitropyridine and 3-hydroxy-2-nitropyridine. Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy, 70(3), 524-531.
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There are 51 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Uğur Soykan

Sedat Çetin

Gurcan Yildirim

Project Number BAP-2014.03.03.686.
Publication Date September 15, 2020
Published in Issue Year 2020 Volume: 9 Issue: 2

Cite

APA Soykan, U., Çetin, S., & Yildirim, G. (2020). Experimental and Theoretical Approaches for the Characterization of the Novel ((Ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(4,1-phenylene) Diacrylate Molecule. Journal of New Results in Science, 9(2), 17-31.
AMA Soykan U, Çetin S, Yildirim G. Experimental and Theoretical Approaches for the Characterization of the Novel ((Ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(4,1-phenylene) Diacrylate Molecule. JNRS. September 2020;9(2):17-31.
Chicago Soykan, Uğur, Sedat Çetin, and Gurcan Yildirim. “Experimental and Theoretical Approaches for the Characterization of the Novel ((Ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(4,1-Phenylene) Diacrylate Molecule”. Journal of New Results in Science 9, no. 2 (September 2020): 17-31.
EndNote Soykan U, Çetin S, Yildirim G (September 1, 2020) Experimental and Theoretical Approaches for the Characterization of the Novel (Ethane-1,2-diylbis(azanediyl) bis(carbonyl) bis(4,1-phenylene) Diacrylate Molecule. Journal of New Results in Science 9 2 17–31.
IEEE U. Soykan, S. Çetin, and G. Yildirim, “Experimental and Theoretical Approaches for the Characterization of the Novel ((Ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(4,1-phenylene) Diacrylate Molecule”, JNRS, vol. 9, no. 2, pp. 17–31, 2020.
ISNAD Soykan, Uğur et al. “Experimental and Theoretical Approaches for the Characterization of the Novel ((Ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(4,1-Phenylene) Diacrylate Molecule”. Journal of New Results in Science 9/2 (September 2020), 17-31.
JAMA Soykan U, Çetin S, Yildirim G. Experimental and Theoretical Approaches for the Characterization of the Novel ((Ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(4,1-phenylene) Diacrylate Molecule. JNRS. 2020;9:17–31.
MLA Soykan, Uğur et al. “Experimental and Theoretical Approaches for the Characterization of the Novel ((Ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(4,1-Phenylene) Diacrylate Molecule”. Journal of New Results in Science, vol. 9, no. 2, 2020, pp. 17-31.
Vancouver Soykan U, Çetin S, Yildirim G. Experimental and Theoretical Approaches for the Characterization of the Novel ((Ethane-1,2-diylbis(azanediyl))bis(carbonyl))bis(4,1-phenylene) Diacrylate Molecule. JNRS. 2020;9(2):17-31.


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