Investigation of Benzimidazole Derivates as Corrosion Inhibitor by DFT

Burak Tüzün

doi:10.17776/csj.412611

Research Article

Investigation of Benzimidazole Derivates as Corrosion Inhibitor by DFT

Year 2019, , 396 - 405, 30.06.2019

Burak Tüzün

https://doi.org/10.17776/csj.412611

Cited By: 13

Abstract

Benzimidazole derivates are investigated the
activity of corrosion inhibitor molecules.In quantum chemical calculation,
different parameters such as E_HOMO, E_LUMO, ∆E (HOMO-LUMO
energy gap), electronegativity, chemical hardness, global softness,
nucleophilicity are calculated by Gaussian 09 software. Studied molecules were
performed using the Hartree-Fock (HF) and Becke, 3-parameter, Lee-Yang-Parr
(B3LYP) method with sdd, cep-4g, 3-21G, 6-31G, 6-31++G, lanl2dz basis set in
gas and aqueous phase. We can see the corrosion inhibitor ranking as: 4NPBI
> 4APBI > 2NPBI > 2APBI > 4BPBI > 4MPBI > 4CPBI > PBI in
B3lyp method with sdd and lanl2dz.

Keywords

Benzimidazole, DFT, corrosion, activity

References

Dutta, A., Saha, S. K., Adhikari, U., Banerjee, P., & Sukul, D.,Effect of substitution on corrosion inhibition properties of 2-(substituted phenyl) benzimidazole derivatives on mild steel in 1 M HCl solution: a combined experimental and theoretical approach. Corrosion Science 123 (2017) 256-266.
Dennington R.D., Keith T.A., Millam J.M., GaussView 5.0, 2009. Wallingford CT.
Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Caricato H., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnerberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Nega R., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Daprich S., Daniels A.D., Farkas A., Foreaman J.B., Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision D.01, Gaussian, Inc., WallingfordCT, 2009.
Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Caricato H., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnerberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Nega R., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Daprich S., Daniels A.D., Farkas A., Foreaman J.B., Ortiz JV, Cioslowski J, Fox DJ., Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009.
Becke A.D., A new mixing of Hatree-Fock and local density-functional theories, J.Chem. Phys. 98 (1993) 1372-1377.
WibergK.B.. Basis set effects on calculated geometries: 6-311++G** vs. aug-cc-pVDZ. J. Comput. Chem. 25 (2004) 1342–1346.
Beck A.D., Density-functional thermochemistry III. the role of exact, Exchange the journal of chemical physics 98 (1993) 5648-5652.
Lee C., Yang W., Parr R.G., Development of the Colle-Savletti correlation-energy formula into a functional of the electron density, Physical Review 37 (1988) 785-789.
Kaya S., Banerjee P., Saha S. K., Tüzün B., Kaya C., Theoretical evaluation of some benzotriazole and phospono derivatives as aluminum corrosion inhibitors: DFT and molecular dynamics simulation approaches, RSC advances 6 (2016) 74550-74559.
Kaya S., Tüzün B., Kaya C., Obot I.B., Determination of corrosion inhibition effects of amino acids: Quantum chemical and molecular dynamic simulation study, Journal of the Taiwan Institute of Chemical Engineers 58 (2016) 528-553.
Kaya S., Kaya C., Guo L., Kandemirli F., Tüzün B., Uğurlu İ., Madkour L.H., Saraçoğlu M., Quantum chemical and molecular dynamics simulation studies on inhibition performances of some thiazole and thiadiazole derivatives against corrosion of iron. Journal of Molecular Liquids 219 (2016) 497-504.
Tüzün B., Selectivity of Salicylaldoxime and its Derivatives, Journal of New Results in Science 3-5 (2014) 67-85.
E. Kose, A. Atac, F. Bardak, the structural and spectroscopic investigation of 2-chloro-3-methylquinoline by DFT method and UV–Vis, NMR and vibrational spectral techniques combined with molecular docking analysis. Journal of Molecular Structure, 1163 (2018) 147-160.
Z. Zhang, W. Li, W. Zhang, X. Huang, L. Ruan, L. Wu, Experimental, quantum chemical calculations and molecular dynamics (MD) simulation studies of methionine and valine as corrosion inhibitors on carbon steel in phase change materials (PCMs) solution. Journal of Molecular Liquids, 272 (2018) 528-538.
R. Nabah, F. Benhiba, Y. Ramli, M. Ouakki, M. Cherkaoui, H. Oudda, A. Zarrouk, Corrosion Inhibition Study of 5, 5-diphenylimidazolidine-2, 4-dione for Mild Steel Corrosion in 1 M HCl Solution: Experimental, Theoretical Computational and Monte Carlo Simulations Studies. Analytical & Bioanalytical Electrochemistry, 10(10) (2018) 1375-1398.
M. Alam, D.U. Lee, Synthesis, spectroscopic and computational studies of 2-(thiophen-2-yl)-2, 3-dihydro-1H-perimidine: An enzymes inhibition study. Computational biology and chemistry, 64 (2016) 185-201.
Madkour L.H., Elshamy I.H. Experimental and computational studies on the inhibition performances of benzimidazole and its derivatives for the corrosion of copper in nitric acid. Int. J. Ind. Chem. 7 (2016) 195–221.
Pearson RG. Chemical hardness: applications from molecules to solids. Germany: Wiley-VCH: Weinheim; 1997.
Obot I.B., Obi-Egbedi N.O., Eselo A.O., Anticorrosion potential of 2-mesityl-1H-imidazol[4,5-][1,10]-phenanthroline on mild steel in sulfuric acid solution; experimental and theoretical study, Ind. Eng. Chem. Res. 50 (2011) 2098-2110.
Makov G., Chemical hardness in density functional theoryJ. Phys. Chem. 99 (1995) 9337-9339
Pearson R.G., Hard and soft acids and bases, J. Am. Chem. Soc. 85 (1963) 3533-3539
Pearson R.G., Hard and soft acids and bases, HSAB, part 1: Fundamental principles, J. Chem. Educ. 45 (1968) 581-587.
Koopmans T., Ordering of wave functions and eigen-energies to the individual electrons of an atom, Physica, 1 (1993) 104-113.
Sanderson R.T., Chemical bond and bond energy, Academic Press, New York 1976.
Sanderson R.T., Electronegativities in inorganic chemistry, J. Chem. Educ. 31 (1954) 2-7.
Özalp A.; Yavuz S. Ç.; Sabancı N.; Çopur F.; Kökbudak Z.; Sarıpınar E. 4D-QSAR investigation and pharmacophore identification of pyrrolo[2,1-c][1,4] benzodiazepines using electron conformational-genetic algorithm method. SAR and QSAR in Environmental Research27-4 (2016) 317-342.
Tüzün B., Yavuz S. Ç., Sarıpınar E., 4D-QSAR analysis and pharmacophore modeling: propoxy methylphenyl oxasiazole derivatives by electron conformatitional-genetic algorithm method, Journal of Physical and Theoretical Chemistry of Islamic Azad University of Iran14-2 (2018) 149-164.

DFT ile benzimidazol türevlerinin korozyon inhibitörü olarak incelenmesi

Year 2019, , 396 - 405, 30.06.2019

Burak Tüzün

https://doi.org/10.17776/csj.412611

Cited By: 13

Abstract

Benzimidazol türevleri, korozyon önleyici moleküllerin aktivitesini
araştırıldı. Kuantum kimyasal hesaplamasında, E_HOMO, E_LUMO,
∆E (HOMO-LUMO enerji aralığı), elektronegatiflik, kimyasal sertlik, global
yumuşaklık, nükleofilik gibi farklı parametreler gaussian 09 yazılımı ile
hesaplandı. Çalışılan moleküller, Hartree-Fock (HF) ve Becke, 3-parametre
Lee-Yang-Parr (B3LYP) yöntemi kullanılarak sdd, cep-4g, 3-21G, 6-31G, 6-31 ++
G, lanl2dz temel sette gaz ve sulu fazda hesaplamaları yapıldı. Korozyon
inhibitörü sıralamasını aşağıdaki gibi görebiliriz: 4NPBI> 4APBI>
2NPBI> 2APBI> 4BPBI> 4MPBI> 4CPBI> PBI, b3lyp metodunda lanl2dz
ve sdd settinde.

Keywords

Benzimidazol, DFT, korozyon, aktivite

References

Dutta, A., Saha, S. K., Adhikari, U., Banerjee, P., & Sukul, D.,Effect of substitution on corrosion inhibition properties of 2-(substituted phenyl) benzimidazole derivatives on mild steel in 1 M HCl solution: a combined experimental and theoretical approach. Corrosion Science 123 (2017) 256-266.
Dennington R.D., Keith T.A., Millam J.M., GaussView 5.0, 2009. Wallingford CT.
Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Caricato H., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnerberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Nega R., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Daprich S., Daniels A.D., Farkas A., Foreaman J.B., Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision D.01, Gaussian, Inc., WallingfordCT, 2009.
Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Caricato H., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnerberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Nega R., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Daprich S., Daniels A.D., Farkas A., Foreaman J.B., Ortiz JV, Cioslowski J, Fox DJ., Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009.
Becke A.D., A new mixing of Hatree-Fock and local density-functional theories, J.Chem. Phys. 98 (1993) 1372-1377.
WibergK.B.. Basis set effects on calculated geometries: 6-311++G** vs. aug-cc-pVDZ. J. Comput. Chem. 25 (2004) 1342–1346.
Beck A.D., Density-functional thermochemistry III. the role of exact, Exchange the journal of chemical physics 98 (1993) 5648-5652.
Lee C., Yang W., Parr R.G., Development of the Colle-Savletti correlation-energy formula into a functional of the electron density, Physical Review 37 (1988) 785-789.
Kaya S., Banerjee P., Saha S. K., Tüzün B., Kaya C., Theoretical evaluation of some benzotriazole and phospono derivatives as aluminum corrosion inhibitors: DFT and molecular dynamics simulation approaches, RSC advances 6 (2016) 74550-74559.
Kaya S., Tüzün B., Kaya C., Obot I.B., Determination of corrosion inhibition effects of amino acids: Quantum chemical and molecular dynamic simulation study, Journal of the Taiwan Institute of Chemical Engineers 58 (2016) 528-553.
Kaya S., Kaya C., Guo L., Kandemirli F., Tüzün B., Uğurlu İ., Madkour L.H., Saraçoğlu M., Quantum chemical and molecular dynamics simulation studies on inhibition performances of some thiazole and thiadiazole derivatives against corrosion of iron. Journal of Molecular Liquids 219 (2016) 497-504.
Tüzün B., Selectivity of Salicylaldoxime and its Derivatives, Journal of New Results in Science 3-5 (2014) 67-85.
E. Kose, A. Atac, F. Bardak, the structural and spectroscopic investigation of 2-chloro-3-methylquinoline by DFT method and UV–Vis, NMR and vibrational spectral techniques combined with molecular docking analysis. Journal of Molecular Structure, 1163 (2018) 147-160.
Z. Zhang, W. Li, W. Zhang, X. Huang, L. Ruan, L. Wu, Experimental, quantum chemical calculations and molecular dynamics (MD) simulation studies of methionine and valine as corrosion inhibitors on carbon steel in phase change materials (PCMs) solution. Journal of Molecular Liquids, 272 (2018) 528-538.
R. Nabah, F. Benhiba, Y. Ramli, M. Ouakki, M. Cherkaoui, H. Oudda, A. Zarrouk, Corrosion Inhibition Study of 5, 5-diphenylimidazolidine-2, 4-dione for Mild Steel Corrosion in 1 M HCl Solution: Experimental, Theoretical Computational and Monte Carlo Simulations Studies. Analytical & Bioanalytical Electrochemistry, 10(10) (2018) 1375-1398.
M. Alam, D.U. Lee, Synthesis, spectroscopic and computational studies of 2-(thiophen-2-yl)-2, 3-dihydro-1H-perimidine: An enzymes inhibition study. Computational biology and chemistry, 64 (2016) 185-201.
Madkour L.H., Elshamy I.H. Experimental and computational studies on the inhibition performances of benzimidazole and its derivatives for the corrosion of copper in nitric acid. Int. J. Ind. Chem. 7 (2016) 195–221.
Pearson RG. Chemical hardness: applications from molecules to solids. Germany: Wiley-VCH: Weinheim; 1997.
Obot I.B., Obi-Egbedi N.O., Eselo A.O., Anticorrosion potential of 2-mesityl-1H-imidazol[4,5-][1,10]-phenanthroline on mild steel in sulfuric acid solution; experimental and theoretical study, Ind. Eng. Chem. Res. 50 (2011) 2098-2110.
Makov G., Chemical hardness in density functional theoryJ. Phys. Chem. 99 (1995) 9337-9339
Pearson R.G., Hard and soft acids and bases, J. Am. Chem. Soc. 85 (1963) 3533-3539
Pearson R.G., Hard and soft acids and bases, HSAB, part 1: Fundamental principles, J. Chem. Educ. 45 (1968) 581-587.
Koopmans T., Ordering of wave functions and eigen-energies to the individual electrons of an atom, Physica, 1 (1993) 104-113.
Sanderson R.T., Chemical bond and bond energy, Academic Press, New York 1976.
Sanderson R.T., Electronegativities in inorganic chemistry, J. Chem. Educ. 31 (1954) 2-7.
Özalp A.; Yavuz S. Ç.; Sabancı N.; Çopur F.; Kökbudak Z.; Sarıpınar E. 4D-QSAR investigation and pharmacophore identification of pyrrolo[2,1-c][1,4] benzodiazepines using electron conformational-genetic algorithm method. SAR and QSAR in Environmental Research27-4 (2016) 317-342.
Tüzün B., Yavuz S. Ç., Sarıpınar E., 4D-QSAR analysis and pharmacophore modeling: propoxy methylphenyl oxasiazole derivatives by electron conformatitional-genetic algorithm method, Journal of Physical and Theoretical Chemistry of Islamic Azad University of Iran14-2 (2018) 149-164.

There are 27 citations in total.

Details

Primary Language	English
Journal Section	Natural Sciences
Authors	Burak Tüzün 0000-0002-0420-2043
Publication Date	June 30, 2019
Submission Date	April 4, 2018
Acceptance Date	December 17, 2018
Published in Issue	Year 2019

Cite

APA	Tüzün, B. (2019). Investigation of Benzimidazole Derivates as Corrosion Inhibitor by DFT. Cumhuriyet Science Journal, 40(2), 396-405. https://doi.org/10.17776/csj.412611