Synthesis and Evaluation of Corrosion Inhibiting Activity of New Molecular Hybrids Containing the Morpholine, 1,4-Naphthoquinone, 7-Chloroquinoline and 1,3,5-Triazine Cores — Oak Academic Publishing
Research ArticleOpen AccessGoogle Scholar indexed
Synthesis and Evaluation of Corrosion Inhibiting Activity of New Molecular Hybrids Containing the Morpholine, 1,4-Naphthoquinone, 7-Chloroquinoline and 1,3,5-Triazine Cores
Laboratório de Síntese Organica Aplicada, Departamento de Química, Universidade Federal do Espírito Santo, Vitória, Brasil
,
Laboratório de Síntese Organica Aplicada, Departamento de Química, Universidade Federal do Espírito Santo, Vitória, Brasil
,
Laboratório de Pesquisa e Desenvolvimento em Eletroquímica, Departamento de Química, Universidade Federal do Espírito Santo, Vitória, Brasil
,
Laboratório de Pesquisa e Desenvolvimento em Eletroquímica, Departamento de Química, Universidade Federal do Espírito Santo, Vitória, Brasil
,
Today at School of Chemistry, Cardiff University, Cardiff, United Kingdom
,
Laboratório de Química Computacional, Instituto de Química, Universidade Federal Fluminense, Niterói, Brasil
,
Laboratório de Química Computacional, Instituto de Química, Universidade Federal Fluminense, Niterói, Brasil
,
Laboratório de Síntese Organica Aplicada, Departamento de Química, Universidade Federal do Espírito Santo, Vitória, Brasil
1 Laboratório de Síntese Organica Aplicada, Departamento de Química, Universidade Federal do Espírito Santo, Vitória, Brasil
2 Laboratório de Síntese Organica Aplicada, Departamento de Química, Universidade Federal do Espírito Santo, Vitória, Brasil
3 Laboratório de Pesquisa e Desenvolvimento em Eletroquímica, Departamento de Química, Universidade Federal do Espírito Santo, Vitória, Brasil
4 Laboratório de Pesquisa e Desenvolvimento em Eletroquímica, Departamento de Química, Universidade Federal do Espírito Santo, Vitória, Brasil
5 Today at School of Chemistry, Cardiff University, Cardiff, United Kingdom
6 Laboratório de Química Computacional, Instituto de Química, Universidade Federal Fluminense, Niterói, Brasil
7 Laboratório de Química Computacional, Instituto de Química, Universidade Federal Fluminense, Niterói, Brasil
8 Laboratório de Síntese Organica Aplicada, Departamento de Química, Universidade Federal do Espírito Santo, Vitória, Brasil
Three molecules containing morpholine, 1,4-naphthoquinone, 7-chloroquinoline and 1,3,5-triazine cores, scaffolds with recognized ant i-corrosive activity, were synthesized and had their anticorrosive activity evaluated through potentiodynamic polarization and electrochemical impedance studies. Both studies were conducted in a simulated production water medium containing 150 , 000 mg·L - 1 Cl - and 5 mg·L - 1 S 2 - . Corrosion inhibition efficiency ranged from 6 7 % - 8 6 %, amongst which the naphthoquinone-containing derivative (compound 1 ) was the most effective. These compounds act through formation of a protective film on the surface of AISI 316 stainless steel. Investigation of the molecular properties of the prepared inhibitors by DFT calculations revealed that the LUMO energy and chemical hardness of the molecules can be directly correlated with their inhibition efficiency.
Pinto, A.V. and De Castro, S.L. (2009) The Trypanocidal Activity of Naphthoquinones: A Review. Molecules, 14, 4570-4590. https://doi.org/10.3390/molecules14114570
Pereyra, C.E., Dantas, R.F., Ferreira, S.B., Gomes, L.P. and Silva-Jr., F.P. (2019) The Diverse Mechanisms and Anticancer Potential of Naphthoquinones. Cancer Cell International, 19, 207.
Hook, I., Mills, C. and Sherida, H. (2014) Bioactive Naphthoquinones from Higher Plants, Studies in Natural Product Chemistry. Elsevier Science Publisher, Amsterdam. https://doi.org/10.1016/B978-0-444-63294-4.00005-X
Shearer, M.J. and Newman, P. (2008) Metabolism and Cell Biology of Vitamin K. Thrombosis and Haemostasis, 100, 530-547. https://doi.org/10.1160/TH08-03-0147
Griffiths, J. (2006) Ullmann’s Encyclopedia of Industrial Chemistry. Wiley VCH, Weinheim.
Widhalm, J.R. and Rhodes, D. (2016) Biosynthesis and Molecular Actions of Specialized 1,4-Naphthoquinone Natural Products Produced by Horticultural Plants. Horticulture Research, 3, Article ID: 16046. https://doi.org/10.1038/hortres.2016.46
Ostovari, A., Hoseinieh, S.M., Peikari, M., Shadizadeh, S.R. and Hashemi, S.J. (2009) Corrosion Inhibition of Mild Steel in 1 M HCl Solution by Henna Extract: A Comparative Study of the Inhibition by Henna and Its Constituents (Lawsone, Gallic Acid, α-D-Glucose and Tannic Acid). Corrosion Science, 51, 1935-1949. https://doi.org/10.1016/j.corsci.2009.05.024
Qiu, H.-Y., Wang, P.F., Lin, H.-Y., Tang, C.-Y., Zhu, H.-L. and Yang, Y.-H. (2018) Naphthoquinones: A Continuing Source for Discovery of Therapeutic Antineoplastic Agents. Chemical Biology & Drug Design, 91, 681-690. https://doi.org/10.1111/cbdd.13141
Chaudhary, A., Khurana, J.M. (2016) 2-Hydroxy-1, 4-Naphthoquinone: A Versatile Synthon in Organic Synthesis. Current Organic Chemistry, 20, 1314-1344. https://doi.org/10.2174/1385272820666151125231522
Kumagai, Y., Shinkai, Y., Miura, T. and Cho, A.K. (2011) The Chemical Biology of Naphthoquinones and Its Environmental Implications. Annual Review of Pharmacology, 52, 221-247. https://doi.org/10.1146/annurev-pharmtox-010611-134517
Marella, A., Tanwar, O.P., Saha, R., Ali, M.R., Srivastava, S., Akhter, M., Shaquiquzzaman, M. and Alam, M.M. (2013) Quinoline: A Versatile Heterocyclic. Saudi Pharmaceutical Journal, 21, 1-12. https://doi.org/10.1016/j.jsps.2012.03.002
Nainwal, L.M., Tasneem, S., Akhtar, W., Verma, G., Khan, M.F., Parvez, S., Shaquiquzzaman, M., Akhter, M. and Alam, M.M. (2019) Green Recipes to Quinoline: A Review. European Journal of Medicinal Chemistry, 164, 121-170. https://doi.org/10.1002/med.21466
Shang, X.-F., Morris-Natschke, S.L., Liu, Y.-Q., Guo, X., Xu, X.-S., Goto, M., Li, J.-C., Yang, G.-Z. and Lee, K.-H. (2018) Biologically Active Quinoline and Quinazoline Alkaloids Part I. Medicinal Research Review, 38, 775-828.
Jain, S., Chandra, V., Jain, P.K., Pathak, K., Pathak, D. and Vaidya, A. (2019) Comprehensive Review on Current Developments of Quinoline-Based Anticancer Agents. Arabian Journal of Chemistry, 12, 4920-4946. https://doi.org/10.1016/j.arabjc.2016.10.009
Chung, P.-Y., Bian, Z.-X., Pun, H.-Y., Chan, D., Chan, A.S.-C., Chui, C.-H., Tang, J.C.-O. and Lam, K.-H. (2015) Recent Advances in Research of Natural and Synthetic Bioactive Quinolines. Future Medicinal Chemistry, 7, 947-967. https://doi.org/10.4155/fmc.15.34
Ram, V.J., Sethi, A., Nath, M. and Pratap, R. (2019) Six-Membered Heterocycles. The Chemistry of Heterocycles. Elsevier, Amsterdam.
Serullas, A. (1828) Annales de Chimie et de Physique, 38, 379.
Blotny, G. (2006) Recent Applications of 2,4,6-Trichloro-1,3,5-Triazine and Its Derivatives in Organic Synthesis. Tetrahedron, 62, 9507-9522. https://doi.org/10.1016/j.tet.2006.07.039
Sharma, A., El-Faham, A., De La Torre, B.G. and Alberico, F. (2018) Exploring the Orthogonal Chemoselectivity of 2,4,6-Trichloro-1,3,5-Triazine (TCT) as a Trifunctional Linker with Different Nucleophiles: Rules of the Game. Frontiers in Chemistry, 6, 516. https://doi.org/10.3389/fchem.2018.00516
Rapoport, L. and Smolin, E.M. (2009) The Chemistry of Heterocyclic Compounds: s-Triazines and Derivatives. John Wiley & Sons, Hoboken.
Reis, M.I.P., Romeiro, G.A., Damasceno, R.N., Da Silva, F.C. and Ferreira, V.F. (2013) Síntese e Aplicações de 1,3,5-Triazinanas. Revista Virtual de Química, 5, 283-299. https://doi.org/10.5935/1984-6835.20130027
Singla, P., Luxami, V. and Paul, K. (2015) Triazine as a Promising Scaffold for Its Versatile Biological Behavior. European Journal of Medicinal Chemistry, 102, 39-57. https://doi.org/10.1016/j.ejmech.2015.07.037
Fiorot, R.G., Westphal, R., Lemos, B.C., Romagna, R.A., Gonçalves, P.R., Fernandes, M.R.N., Taranto, A.G. and Greco, S.G. (2019) Synthesis, Molecular Modelling and Anticancer Activities of New Molecular Hybrids Containing 1,4-Naphthoquinone, 7-Chloroquinoline, 1,3,5-Triazine and Morpholine Cores as PI3K and AMPK Inhibitors in the Metastatic Melanoma Cells. Journal of the Brazilian Chemical Society, 30, 1860-1873. https://doi.org/10.21577/0103-5053.20190096
Yrjölä, S., Sarparanta, M., Airaksinen, A.J., Hytti, M., Kauppinen, A., Pasonen-Seppänen, S., Adinolfi, B., Nieri, P., Manera, C., Keinänen, O., Poso, A., Nevalainen, T.J. and Parkkari, T. (2015) Synthesis, in Vitro and in Vivo Evaluation of 1,3,5-Triazines as Cannabinoid CB2 Receptor Agonists. European Journal of Pharmaceutical Sciences, 67, 85-96. https://doi.org/10.1016/j.ejps.2014.11.003
Verma, C., Haque, J., Quraishi, M.A. and Ebenso, E.E. (2019) Aqueous Phase Environmental Friendly Organic Corrosion Inhibitors Derived from One Step Multicomponent Reactions: A Review. Journal of Molecular Liquids, 275, 18-40. https://doi.org/10.1016/j.molliq.2018.11.040
Cardoso, S.P., Reis, F.A., Massapust, F.C., Costa, J.F., Tebaldi, L.S., Araújo, L.F., Silva, M.V.A., Oliveira, T.S., Gomes, J.A.C.P. and Hollauer E. (2005) Avaliação de Indicadores de Uso Diverso como Inibidores de Corrosão. Química Nova, 28, 756-760. https://doi.org/10.1590/S0100-40422005000500004
Vracar, L.M. and Drazicb, D.M. (2002) Adsorption and Corrosion Inhibitive Properties of Some Organic Molecules on Iron Electrode in Sulfuric Acid. Corrosion Science, 44, 1669-1680. https://doi.org/10.1016/S0010-938X(01)00166-4
Nabi, A.S.A. and Hussain, A.A. (2012) Synthesis, Identification and Study of Some New Azo Dyes as Corrosion Inhibitors for Carbon-Steel in Acidic Media. Journal of Basrah Researches, 38, 125-146.
Souza, F.S.D. and Spinelli, A, (2009) Caffeic Acid as a Green Corrosion Inhibitor for Mild Steel. Corrosion Science, 51, 642-649. https://doi.org/10.1016/j.corsci.2008.12.013
Sherif, E.M. and Park, S.M. (2006) Effects of 1,4-Naphthoquinone on Aluminum Corrosion in 0.50 M Sodium Chloride Solutions. Electrochimica Acta, 51, 1313-1321. https://doi.org/10.1016/j.electacta.2005.06.018
Erdogan, S., Safi, Z.S., Isin, D.Ö., Guo, L. and Kaya, C. (2007) A Computational Study on Corrosion Inhibition Performances of Novel Quinoline Derivatives against the Corrosion of Iron. Journal of Molecular Structure, 1134, 751-761. https://doi.org/10.1016/j.molstruc.2017.01.037
Sundaram, R.G. and Sundaravadivelu, M. (2016) Anticorrosion Activity of 8-Quinoline Sulphonyl Chloride on Mild Steel in 1 M HCl Solution. Journal of Metallurgy, 2016, Article ID: 8095203. https://doi.org/10.1155/2016/8095206
Lgaz, H., Salghi, R., Bhat, K.S., Chaouiki, A. and Shubhalaxmi J.S. (2017) Correlated Experimental and Theoretical Study on Inhibition Behavior of Novel Quinoline Derivatives for the Corrosion of Mild Steel in Hydrochloric Acid Solution. Journal of Molecular Liquid, 244, 154-168. https://doi.org/10.1016/j.molliq.2017.08.121
Karthik, R., Muthukrishnan, P., Elangovan, A., Sri Vidhya, M.M., Jeyaprabha, B. and Prakash, P. (2015) Adsorption and Corrosion Inhibiting Behavior of a New S-Triazine Derivative. Protection of Metals and Physical Chemistry of Surfaces, 51, 667-679. https://doi.org/10.1134/S2070205115040152
El-Fahan, A., Dahlous, K.A., Al Othman, Z.A., Al-Lohedan, H.A. and El-Mahdy, G.A. (2016) Sym-Trisubstituted 1,3,5-Triazine Derivatives as Promising Organic Corrosion Inhibitors for Steel in Acidic Solution. Molecules, 21, 436. https://doi.org/10.3390/molecules21040436
Zhao, Q., Tang, T., Dang, P., Zhang, Z. and Wang, F. (2017) The Corrosion Inhibition Effect of Triazinedithiol Inhibitors for Aluminum Alloy in a 1 M HCl Solution. Metals, 7, 44. https://doi.org/10.3390/met7020044
Obot, I.B., Kaya, S., Kaya, C. and Tüzün, B. (2016) Theoretical Evaluation of Triazine Derivatives as Steel Corrosion Inhibitors: DFT and Monte Carlo Simulation Approaches. Research on Chemical Intermediate, 42, 4963-4983. https://doi.org/10.1007/s11164-015-2339-0
Naji, N.J.N., Ujam, O.T., Ibisi, N.E., Ani, J.U., Onuegbu, T.O., Olasunkanmi, L.O. and Ebenso, E.E. (2017) Morpholine and Piperazine Based Carboxamide Derivatives as Corrosion Inhibitors of Mild Steel in HCl Medium. Journal of Molecular Liquids, 230, 652-661. https://doi.org/10.1016/j.molliq.2017.01.075
Jayanthi, K., Sivaraju, M. and Kannan, K. (2012) Inhibiting Properties of Morpholine as Corrosion Inhibitor for Mild Steel in 2N Sulphuric Acid and Phosphoric Acid Medium. European Journal of Chemistry, 9, 2213-2225. https://doi.org/10.1155/2012/904353
Goulart, C.M., Esteves-Souza, A., Martinez-Huitle, C.A., Rodrigues, C.J.F., Maciel, M.A.M. and Echevarria, A, (2013) Experimental and Theoretical Evaluation of Semicarbazones and Thiosemicarbazones as Organic Corrosion Inhibitors. Corrosion Science, 67, 281-291. https://doi.org/10.1016/j.corsci.2012.10.029
Lasia, A. (2014) Electrochemical Impedance Spectroscopy and Its Applications. Springer, New York. https://doi.org/10.1007/978-1-4614-8933-7
http://www.abc.chemistry.bsu.by/vi/analyser/
Mcquarie, D.A. and Simon, J.D. (1997) Physical Chemistry: A Molecular Approach. University Science Book, California.
Zhao, Y. and Truhlar, D.G. (2008) The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals. Theoretical Chemistry Accounts, 120, 215-241. https://doi.org/10.1007/s00214-007-0310-x
Adamo, C. and Barone, V. (1999) Toward Reliable Density Functional Methods without Adjustable Parameters: The PBE0 Model. Journal of Chemical Physics, 110, 6158. https://doi.org/10.1063/1.478522
Mennucci, B., Cancès, E. and Tomasi, J. (1997) Evaluation of Solvent Effects in Isotropic and Anisotropic Dielectrics and in Ionic Solutions with a Unified Integral Equation Method: Theoretical Bases, Computational Implementation, and Numerical Applications. Journal of Physical Chemistry B, 101, 10506-10517. https://doi.org/10.1021/jp971959k
Tomasi, J., Mennuci, B. and Cancès, E. (1999) The IEF Version of the PCM Solvation Method: An Overview of a New Method Addressed to Study Molecular Solutes at the QM Ab Initio Level. Journal of Molecular Structure: Teochem, 464, 211. https://doi.org/10.1016/S0166-1280(98)00553-3
Panichayupakaranant, P. and Reanmongkol, W. (2002) Evaluation of Chemical Stability and Skin Irritation of Lawsone Methyl Ether in Oral Base. Pharmaceutical Biology, 40, 429-432. https://doi.org/10.1076/phbi.40.6.429.8443
Delarmelina, M., Daltoé, R.D., Cerri, M.F., Madeira, K.P., Rangel, L.B.A., Lacerda Jr., V., Romão, W., Taranto, A.G. and Greco, S.J. (2015) Synthesis, Antitumor Activity and Docking of 2,3-(Substituted)-1,4-Naphthoquinone Derivatives Containing Nitrogen, Oxygen and Sulfur. Journal of the Brazilian Chemical Society, 26, 1804-1816. https://doi.org/10.5935/0103-5053.20150157
Delarmelina, M., Greco, S.J. and Carneiro, J.W.M. (2017) Single Step Mechanism for Nucleophilic Substitution of 2,3-Dichloro Naphthoquinone Using Nitrogen, Oxygen and Sulfur Nucleophiles: A DFT Approach. Tetrahedron, 73, 4363-4370. https://doi.org/10.1016/j.tet.2017.05.095
Venkatesan, A.M., Dehnhardt, C.M., Santos, E.D., Chen, Z., Dos Santos, O., Ayral-Kaloustian, S., Khafizova, G., Brooijmans, N., Mallon, R., Hollander, I., Feldberg, L., Lucas, J., Yu, K., Gibbons, J., Abraham, R.T., Chaudhary, I. and Mansour, T.S. (2010) Bis(Morpholino-1,3,5-Triazine)Derivatives: Potent Adenosine 5’-Triphosphate Competitive Phosphatidylinositol-3-Kinase/Mammalian Target of Rapamycin Inhibitors: Discovery of Compound 26 (PKI-587), a Highly Efficacious Dual Inhibitor. Journal of Medicinal Chemistry, 26, 2636-2645. https://doi.org/10.1021/jm901830p
Carmo, A.M.L., Silva, F.M.C., Machado, P.A., Fontes, A.P.S., Pavan, F.R., Leite, C.Q.F., De A. Leite, S.R., Coimbra, E.S. and Silva, A.D. (2011) Synthesis of 4-Aminoquinoline Analogues and Their Platinum(II) Complexes as New Antileishmanial and Antitubercular Agents. Biomedicine & Pharmacotherapy, 65, 204-209. https://doi.org/10.1016/j.biopha.2011.01.003
Uhlig, H.H. and Revie, R.W. (2008) Corrosion and Corrosion Control: An Introduction to Corrosion Science and Engineering, Wiley Interscience, New Jersey.
Moreira, R.R., Soares, T.F., Gontijo, L.C., Castro, E.V.R. and Ribeiro, J. (2016) Using the Imidazole and Benzimidazole as Corrosion Inhibitor of UNS S31803 Duplex Stainless Steel. International Journal of Engineering Research & Management Technology, 03, 17-21.
Bard, A.J. and Faulkner, L.R. (2001) Electrochemical Methods: Fundamentals and Applications. 2nd Edition, Wiley, New York.
Verma, C., Sorour, A.A., Ebenso, E.E. and Quraishi, M.A. (2018) Inhibition Performance of Three Naphthyridine Derivatives for Mild Steel Corrosion in 1M HCl: Computation and Experimental Analyses. Results in Physics, 10, 504-511. https://doi.org/10.1016/j.rinp.2018.06.054