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PROBING THE STRUCTURE-CORROSION INHIBITION PROPERTY RELATIONSHIP OF PYRROLE OLIGOMERS WITH DFT CALCULATIONS

Yıl 2019, Cilt: 61 Sayı: 1, 55 - 68, 31.12.2019

Gökhan Gece Semra Bilgiç

Öz

Density functional theory (DFT) calculations on pyrrole oligomers were carried out at the B3LYP/6-311+G(d,p) level to search the relationship between the molecular structure and corrosion inhibition. The electronic properties such as the highest occupied
molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) energy levels, energy gap (LUMO-HOMO) and dipole moment were computed. It was found that these electronic values can explain some features of the inhibition phenomena.

Anahtar Kelimeler

Pyrrole Polypyrrole Corrosion Inhibition Density Functional Theory

Kaynakça

  • G. H. Koch, M. P. H. Brongers, N. G. Thompson, Y. P. Virmani and J. H. Payer, Corrosion costs and preventive strategies in the United States. U.S. Federal Highway Administration Report, 2002.
  • F. Presuel-Moreno, M. A. Jakab, N. Tailleart, M. Goldman and J. R. Scully, Corrosionresistant metallic coatings. Materials Today 11 (2008) 14-23.
  • G. O. Ilevbare, J. Yuan, R. G. Kelly and J. R. Scully, Inhibition of the corrosion of AA 2024: chromate conversion coating versus chromate additions. Corrosion 56 (2000) 227-242.
  • I. M. Zin, R. L. Howard, S. J. Badger, J. D. Scantlebury and S. B. Lyon, The mode of action of chromate inhibitor in epoxy primer on galvanized steel. Progress in Organic Coatings 33 (1998) 203-210.
  • M. Bazzaoui, J. I. Martins, E. A. Bazzaoui, T. C. Reis and L. Martins, Pyrrole electropolymerization on copper and brass in a single-step process from aqueous solution. Journal of Applied Electrochemistry 34 (2004) 815-822.
  • B. N. Grgur, N. V. Krstajić, M. V. Vojnović, Č. Lačnjevac and Lj. Gajić-Krstajić, The influence of polypyrrole films on the corrosion behavior of iron in acid sulfate solutions. Progress in Organic Coatings 33 (1998) 1-6.
  • D. W. Deberry, Modification of the electrochemical and corrosion behavior of stainless steels with an electroactive coating. Journal of the Electrochemical Society 132 (1985) 1022-1026.
  • A. Michalik and M. Rohwerder, Conducting polymers for corrosion protection: a critical view. Zeitschrift für Physikalische Chemie, 219 (2005) 1547-1559.
  • P. Zarras, N. Anderson, C. Webber, D. J. Irwin, A. Guenthner and J.D. Stenger-Smith, Progress in using conductive polymers as corrosion-inhibiting coatings. Radiation Physics and Chemistry 68 (2003) 387-394.
  • H. Nguyen Thi Le, M. C. Bernard, B. Garcia-Renaud and C. Deslouis, Raman spectroscopy analysis of polypyrrole films as protective coatings on iron. Synthetic Metals, 140 (2004) 287-293.
  • J. Reut, A. Öpik and K. Idla, Corrosion behavior of polypyrrole coated mild steel. Synthetic Metals, 102 (1999) 1392-1393.
  • G. Gece, The use of quantum chemical methods in corrosion inhibitor studies. Corrosion Science, 50 (2008) 2981-2992.
  • L. T. Jr. Sein, Y. Wei and S. A. Jansen, The role of adsorption of aniline trimers on the corrosion inhibition process : a ZINDO/1 study. Computational and Theoretical Polymer Science, 11 (2001) 83-88.
  • L. T. Jr. Sein, Y. Wei and S. A. Jansen, Corrosion inhibition by aniline oligomers through charge transfer: a DFT approach. Synthetic Metals 143 (2004) 1-12.
  • A. Yurt, V. Bütün and B. Duran, Effect of the molecular weight and structure of some novel water-soluble triblock copolymers on the electrochemical behaviour of mild steel. Materials Chemistry and Physics 105 (2007) 114-121.
  • R. Hasanov, S. Bilgiç and G. Gece, Experimental and theoretical studies on the corrosion properties of some conducting polymer coatings. Journal of Solid State Electrochemistry 15 (2011) 1063-1070.
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman and D. J. Fox, Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT, 2009.
  • T. A. Skotheim, R. L. Elsenbaumer and J. R. Reynolds, Handbook of conducting polymers, Marcel Dekker Inc. New York, 1998.
  • L. Nygaard, J.T. Nielsen, J. Kirchheiner, G. Maltesen, J. Rastrup-Andersen and G.O. Sørensen, Microwave spectra of isotopic pyrroles. Molecular structure, dipole moment, and 14N quadrupole coupling constants of pyrrole. Journal of Molecular Structure, 3 (1969) 491-506.
  • G. R. Hutchison, M. A. Ratner and T. J. Marks, Accurate prediction of band gaps in neutral heterocyclic conjugated polymers. Journal of Physical Chemistry A, 106 (2002) 10596-10605.
  • T. Tamm, J. Tamm and M. Karelson, Theoretical study of the effect of counterions on the structure of pyrrole oligomers. International Journal of Quantum Chemistry, 88 (2002) 296-301.
  • K. Fukui, Theory of orientation and stereoselection, Springer-Verlag, New York, 1975.
  • J. Casanovas, E. Armelin, J. I. Iribarren, C. Alemán and F. Liesa, La modelización molecular como herramienta para el diseño de nuevos polímeros conductores. Polimeros, 15 (20059 239-244.
  • J. L. Brédas, R. Silbey, D. S. Boudreaux and R. R. Chance, Chain-length dependence of electronic and electrochemical properties of conjugated systems - polyacetylene, polyphenylene, polythiophene, and polypyrrole. Journal of the American Chemical Society, 105 (1983) 6555-6559.
  • G. Zotti, S. Martina, G. Wegner and A. D. Schlüter, Well-defined pyrrole oligomers: electrochemical and UV/vis studies. Advanced Materials, 4 (1992) 798-801.
  • P. Audebert, J. M. Catel, G. L. Coustumer, V. Duchenet and P. Hapiot, Electrochemical oxidation of five-unit heterocycles: a discussion on the possible dimerization mechanisms. Journal of Physical Chemistry, 99 (1995) 11923-11929.
  • A. I. Khuri and J. A. Cornell, Response surfaces: Designs and analyses, 2nd ed., (Marcel Dekker Inc., New York, 1996).
  • P. Mutombo and N. Hackerman, The effect of some organophosphorus compounds on the corrosion behaviour of iron 6 M HCl. Anti-Corrosion Methods and Materials, 45 (1998) 413-418.
  • M. Karelson and V. S. Lobanov, Quantum chemical descriptors in QSAR/QSPR studies. Chemical Reviews, 96 (1996) 1027-1043.
  • S. Millefiori and A. Alparone, Ab initio and density functional theory study of the structure and torsional potential of pyrrole oligomers. Journal of Chemical Society Faraday Transactions, 94 (1998) 25-32.
  • K. Seio, H. Ukawa, K. Shohda and M. Sekine, Computational evaluation of intermolecular interactions of a universal base 3-nitropyrrole in stacked dimers and DNA duplexes. Journal of Biomolecular Structure and Dynamics, 22 (2005) 735-746.
  • A. Stoyanova, G. Petkova and S. D. Peyerimhoff, Correlation between the molecular structure and the corrosion inhibiting effect of some pyrophthalone compounds. Chemical Physics, 279 (2002) 1-6.
  • X. Pang, B. Hou, W. Li, F. Liu, and Z. Yu, 2,3,5-triphenyl-2h-tetrazolium chloride and 2,4,6-tri(2-pyridyl)-s-triazine on the corrosion of mild steel in HCI. Chinese Journal of Chemical Engineering, 15 (2007) 909-915.
  • M. Finšgar, A. Lesar, A. Kokalj and I. Milošev, A comparative electrochemical and quantum chemical calculation study of BTAH and BTAOH as copper corrosion inhibitors in near neutral chloride solution. Electrochimica Acta, 53 (2008) 8287-8297.
  • Y. Yan, W. Li, L. Cai and B. Hou, Electrochemical and quantum chemical study of purines as corrosion inhibitors for mild steel in 1 M HCl solution. Electrochimica Acta, 53 (2008) 5953-5960.

Yıl 2019, Cilt: 61 Sayı: 1, 55 - 68, 31.12.2019

Gökhan Gece Semra Bilgiç

Öz

Kaynakça

  • G. H. Koch, M. P. H. Brongers, N. G. Thompson, Y. P. Virmani and J. H. Payer, Corrosion costs and preventive strategies in the United States. U.S. Federal Highway Administration Report, 2002.
  • F. Presuel-Moreno, M. A. Jakab, N. Tailleart, M. Goldman and J. R. Scully, Corrosionresistant metallic coatings. Materials Today 11 (2008) 14-23.
  • G. O. Ilevbare, J. Yuan, R. G. Kelly and J. R. Scully, Inhibition of the corrosion of AA 2024: chromate conversion coating versus chromate additions. Corrosion 56 (2000) 227-242.
  • I. M. Zin, R. L. Howard, S. J. Badger, J. D. Scantlebury and S. B. Lyon, The mode of action of chromate inhibitor in epoxy primer on galvanized steel. Progress in Organic Coatings 33 (1998) 203-210.
  • M. Bazzaoui, J. I. Martins, E. A. Bazzaoui, T. C. Reis and L. Martins, Pyrrole electropolymerization on copper and brass in a single-step process from aqueous solution. Journal of Applied Electrochemistry 34 (2004) 815-822.
  • B. N. Grgur, N. V. Krstajić, M. V. Vojnović, Č. Lačnjevac and Lj. Gajić-Krstajić, The influence of polypyrrole films on the corrosion behavior of iron in acid sulfate solutions. Progress in Organic Coatings 33 (1998) 1-6.
  • D. W. Deberry, Modification of the electrochemical and corrosion behavior of stainless steels with an electroactive coating. Journal of the Electrochemical Society 132 (1985) 1022-1026.
  • A. Michalik and M. Rohwerder, Conducting polymers for corrosion protection: a critical view. Zeitschrift für Physikalische Chemie, 219 (2005) 1547-1559.
  • P. Zarras, N. Anderson, C. Webber, D. J. Irwin, A. Guenthner and J.D. Stenger-Smith, Progress in using conductive polymers as corrosion-inhibiting coatings. Radiation Physics and Chemistry 68 (2003) 387-394.
  • H. Nguyen Thi Le, M. C. Bernard, B. Garcia-Renaud and C. Deslouis, Raman spectroscopy analysis of polypyrrole films as protective coatings on iron. Synthetic Metals, 140 (2004) 287-293.
  • J. Reut, A. Öpik and K. Idla, Corrosion behavior of polypyrrole coated mild steel. Synthetic Metals, 102 (1999) 1392-1393.
  • G. Gece, The use of quantum chemical methods in corrosion inhibitor studies. Corrosion Science, 50 (2008) 2981-2992.
  • L. T. Jr. Sein, Y. Wei and S. A. Jansen, The role of adsorption of aniline trimers on the corrosion inhibition process : a ZINDO/1 study. Computational and Theoretical Polymer Science, 11 (2001) 83-88.
  • L. T. Jr. Sein, Y. Wei and S. A. Jansen, Corrosion inhibition by aniline oligomers through charge transfer: a DFT approach. Synthetic Metals 143 (2004) 1-12.
  • A. Yurt, V. Bütün and B. Duran, Effect of the molecular weight and structure of some novel water-soluble triblock copolymers on the electrochemical behaviour of mild steel. Materials Chemistry and Physics 105 (2007) 114-121.
  • R. Hasanov, S. Bilgiç and G. Gece, Experimental and theoretical studies on the corrosion properties of some conducting polymer coatings. Journal of Solid State Electrochemistry 15 (2011) 1063-1070.
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman and D. J. Fox, Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT, 2009.
  • T. A. Skotheim, R. L. Elsenbaumer and J. R. Reynolds, Handbook of conducting polymers, Marcel Dekker Inc. New York, 1998.
  • L. Nygaard, J.T. Nielsen, J. Kirchheiner, G. Maltesen, J. Rastrup-Andersen and G.O. Sørensen, Microwave spectra of isotopic pyrroles. Molecular structure, dipole moment, and 14N quadrupole coupling constants of pyrrole. Journal of Molecular Structure, 3 (1969) 491-506.
  • G. R. Hutchison, M. A. Ratner and T. J. Marks, Accurate prediction of band gaps in neutral heterocyclic conjugated polymers. Journal of Physical Chemistry A, 106 (2002) 10596-10605.
  • T. Tamm, J. Tamm and M. Karelson, Theoretical study of the effect of counterions on the structure of pyrrole oligomers. International Journal of Quantum Chemistry, 88 (2002) 296-301.
  • K. Fukui, Theory of orientation and stereoselection, Springer-Verlag, New York, 1975.
  • J. Casanovas, E. Armelin, J. I. Iribarren, C. Alemán and F. Liesa, La modelización molecular como herramienta para el diseño de nuevos polímeros conductores. Polimeros, 15 (20059 239-244.
  • J. L. Brédas, R. Silbey, D. S. Boudreaux and R. R. Chance, Chain-length dependence of electronic and electrochemical properties of conjugated systems - polyacetylene, polyphenylene, polythiophene, and polypyrrole. Journal of the American Chemical Society, 105 (1983) 6555-6559.
  • G. Zotti, S. Martina, G. Wegner and A. D. Schlüter, Well-defined pyrrole oligomers: electrochemical and UV/vis studies. Advanced Materials, 4 (1992) 798-801.
  • P. Audebert, J. M. Catel, G. L. Coustumer, V. Duchenet and P. Hapiot, Electrochemical oxidation of five-unit heterocycles: a discussion on the possible dimerization mechanisms. Journal of Physical Chemistry, 99 (1995) 11923-11929.
  • A. I. Khuri and J. A. Cornell, Response surfaces: Designs and analyses, 2nd ed., (Marcel Dekker Inc., New York, 1996).
  • P. Mutombo and N. Hackerman, The effect of some organophosphorus compounds on the corrosion behaviour of iron 6 M HCl. Anti-Corrosion Methods and Materials, 45 (1998) 413-418.
  • M. Karelson and V. S. Lobanov, Quantum chemical descriptors in QSAR/QSPR studies. Chemical Reviews, 96 (1996) 1027-1043.
  • S. Millefiori and A. Alparone, Ab initio and density functional theory study of the structure and torsional potential of pyrrole oligomers. Journal of Chemical Society Faraday Transactions, 94 (1998) 25-32.
  • K. Seio, H. Ukawa, K. Shohda and M. Sekine, Computational evaluation of intermolecular interactions of a universal base 3-nitropyrrole in stacked dimers and DNA duplexes. Journal of Biomolecular Structure and Dynamics, 22 (2005) 735-746.
  • A. Stoyanova, G. Petkova and S. D. Peyerimhoff, Correlation between the molecular structure and the corrosion inhibiting effect of some pyrophthalone compounds. Chemical Physics, 279 (2002) 1-6.
  • X. Pang, B. Hou, W. Li, F. Liu, and Z. Yu, 2,3,5-triphenyl-2h-tetrazolium chloride and 2,4,6-tri(2-pyridyl)-s-triazine on the corrosion of mild steel in HCI. Chinese Journal of Chemical Engineering, 15 (2007) 909-915.
  • M. Finšgar, A. Lesar, A. Kokalj and I. Milošev, A comparative electrochemical and quantum chemical calculation study of BTAH and BTAOH as copper corrosion inhibitors in near neutral chloride solution. Electrochimica Acta, 53 (2008) 8287-8297.
  • Y. Yan, W. Li, L. Cai and B. Hou, Electrochemical and quantum chemical study of purines as corrosion inhibitors for mild steel in 1 M HCl solution. Electrochimica Acta, 53 (2008) 5953-5960.
Toplam 35 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Research Articles
Yazarlar

Gökhan Gece 0000-0001-9310-5407

Semra Bilgiç 0000-0001-9730-0146

Yayımlanma Tarihi 31 Aralık 2019
Kabul Tarihi 3 Aralık 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 61 Sayı: 1

Kaynak Göster

Vancouver Gece G, Bilgiç S. PROBING THE STRUCTURE-CORROSION INHIBITION PROPERTY RELATIONSHIP OF PYRROLE OLIGOMERS WITH DFT CALCULATIONS. Commun. Fac. Sci. Univ. Ank. Ser. B. 2019;61(1):55-68.
 Kapak Resmi İndir

Communications Faculty of Sciences University of Ankara Series B Chemistry and Chemical Engineering

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