Skip to main content
Log in

Pyrazines as Potential Corrosion Inhibitors for Industrial Metals and Alloys: A Review

  • Published:
Journal of Bio- and Tribo-Corrosion Aims and scope Submit manuscript

Abstract

Pyrazine is an important diazine with the nitrogen atoms occupying the 1,4-positions within an aromatic ring. Pyrazine and its derivatives find great importance in food and medicine courtesy of their chemical characteristics functionality, namely the chemistry of their nitrogen atoms. Based on the known ability of some nitrogen-based compounds to function as excellent corrosion inhibitors for metallic materials in aqueous solutions, pyrazine and its derivatives have been reported as effective corrosion inhibitors. However, these reports are relatively scarce and limited. Herein, we have attempted a review of the known literature investigating the corrosion inhibition properties of pyrazine and its derivatives. They were reported to function as mixed-type inhibitors for steel and Al and Mg alloys. Their adsorption follows the Langmuir isotherm with steel and deviated in the case of Al and Mg alloys. The adsorption of the pyrazine derivatives on steel may be physical or chemical but is purely chemical on Al and Mg alloys. Theoretical correlations with molecular dynamic simulation have also been reviewed. We have also provided future considerations and direction of research on this important multifunctional chemistry.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Bird CW (1992) Heteroaromaticity—a unified aromaticity index. Tetrahedron 48(2):335–340

    CAS  Google Scholar 

  2. Swartz J, Anson FC (1980) A comparison of the staircase voltammetric and polarographic responses of pyrazine and several substituted pyrazines in aqueous acid. J Electroanal Chem Interfacial Electrochem 114(1):117–128

    CAS  Google Scholar 

  3. Wadt WR, Goddard WA III, Dunning TH (1976) The electronic structure of pyrazine. Configuration interaction calculations using an extended basis. J Chem Phys 65:438

    CAS  Google Scholar 

  4. Brown CJ III, Knaust JM (2009) 2,5-Dimethylpyrazine 1,4-dioxide. Acta Cryst Sect E Struct Rep Online 65(12):1600–5368

    Google Scholar 

  5. Wan M, Zou Y, Tan S, Li Y (2010) Two thieno[3,4b]pyrazine-containing copolymers: synthesis, characterization, and application in mercury ions detection. Polym Adv Technol 21:256–262

    CAS  Google Scholar 

  6. Zou YP, Wan MX, Sang GY, Ye MF, Li YF (2008) An alternative copolymer of carbazole and thieno[3,4b]-pyrazine: synthesis and mercury detection. Adv Funct Mater 18(18):2724–2732

    CAS  Google Scholar 

  7. Dokladalova L, Bures F, Kuznik W, Kityk IV, Wojciechowski A, Mikysek T, Almonasy N, Ramaiyan M, Padelkova Z, Kulhanek J, Ludwig M (2014) Dicyanobenzene and dicyanopyrazine derived X-shaped charge-transfer chromophores: comparative and structure–property relationship study. Org Biomol Chem 12:5517–5527

    CAS  Google Scholar 

  8. Zhang X, Mao J, Wang D, Li X, Yang J, Shen Z, Wu W, Li J, Agren H, Hua J (2015) Comparative study on pyrido[3,4-b]pyrazine-based sensitizers by Tuning Bulky donors for dye-sensitized solar cells. ACS Appl Mater Interfaces 7:2760–2771

    CAS  Google Scholar 

  9. Xu L, Zhao Y, Long G, Wang Y, Zhao J, Li D, Li J, Rakesh G, Li Y, Sun H, Sun X, Zhang Q (2015) Synthesis, structure, physical properties and OLED application of pyrazine–triphenylamine fused conjugated compounds. RSC Adv 5:63080–63086. https://doi.org/10.1039/C5RA12654A

    Google Scholar 

  10. Premkumar T, Govindarajan S (2005) Antimicrobial study of pyrazine, pyrazole and imidazole carboxylic acids and their hydrazinium salts. World J Microbiol Biotechnol 21:479–480

    CAS  Google Scholar 

  11. Gobis K, Foks H, Kedzia A, Wierzchowska M, Kwapisz E, Zwolska Z, Kopec A-E (2006) Studies on pyrazine derivatives. XLVII. Synthesis and antibacterial activity of novel pyrazine derivatives with amidoxime moiety. Acta Pol Pharm Drug Res 63(1):39–46

    CAS  Google Scholar 

  12. Kamal A, Ramakrishna G, Raju P, Subba-Rao AV, Viswanath A, Lakshma-Nayak V, Ramakrishna S (2011) Synthesis and anticancer activities of oxindole derived from imidazo[1,5-a]pyrazines. Eur J Med Chem 46(6):2427–2435

    CAS  Google Scholar 

  13. Beldar SV, Jordis U (2009) Synthetic studies towards the antiviral pyrazine derivative T-705. In: 13th electronic conference on synthetic organic chemistry (ECSOC-13), pp 1–30

  14. Meurer LC, Tolman RL, Chapin EW, Saperstein R, Vicario PP, Zrada MM, MacCoss M (1992) Synthesis and hypoglycemic activity of substituted 8-(1-piperazinyl)imidazo[1,2-a]pyrazines. J Med Chem 35(21):3845–3857

    CAS  Google Scholar 

  15. Sai Manzeera A, Sireesha NP, Aswini M, Rao MP, Sree NK, Mallikharjunarao KLN (2013) Synthesis and anti-inflammatory activity of pyrazine derivatives. Asian J Res Pharm Sci Biotechnol 1(1):10–15

    Google Scholar 

  16. Seitz LE, Suling WJ, Reynolds RC (2002) Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives. J Med Chem 45:5604–5606

    CAS  Google Scholar 

  17. Dolezal M, Palek L, Vinsova J, Buchta V, Jampilek J, Kralova K (2006) Substituted pyrazinecarboxamides: synthesis and biological evaluation. Molecules 11:242–256

    CAS  Google Scholar 

  18. Bondarovich HA, Friedel P, Krampl V, Renner JA, Shephard FW, Gianturco MA (1967) Volatile constituents of coffee, Pyrazines and other compounds. J Agric Food Chem 15(6):1093–1099

    CAS  Google Scholar 

  19. Baker GL, Cornell JA, Gorbert DW, O’Keefe SF, Sims CA, Talcott ST (2003) Determination of pyrazine and flavor variations in peanut genotypes during roasting. J Food Sci 68(1):394–400

    CAS  Google Scholar 

  20. Watanabe K, Sato Y (1971) Alkyl-substituted pyrazines and pyridines in the flavor components of shallow fried beef. J Agric Food Chem 19(5):1017–1019

    CAS  Google Scholar 

  21. Nemykin VN, Lukyanets EA (2010) Synthesis of substituted phthalocyanines, Arkivoc: online. J Org Chem 1:136–208

    Google Scholar 

  22. Ormond AB, Freeman HS (2013) Dye sensitizers for photodynamic therapy. Materials 6(3):817–840

    CAS  Google Scholar 

  23. O’Connor AE, Gallagher WM, Byrne AT (2009) Porphyrin and nonporphyrin photosensitizers in oncology: preclinical and clinical advances in photodynamic therapy. J Photochem Photobiol 85:1053–1074

    Google Scholar 

  24. Rosenthal DI, Nurenberg P, Becerra CR, Frenkel EP, Carbone DP, Lum BL, Miller R, Engel J, Young S, Miles D, Renschler MF (1999) A phase I single-dose trial of gadolinium texaphyrin (Gd-Tex), a tumor selective sensitizer detectable by magnetic resonance imaging. J Clin Cancer Res 5:739–745

    CAS  Google Scholar 

  25. Kopranenkov VN, Luk’yanets EA (1995) Porphyrazines: synthesis, properties and application. Russ Chem Bull 44(12):2216–2232

    Google Scholar 

  26. Miwa H, Ishii K, Kobayashi N (2004) Electronic structures of zinc and palladium tetra-azaporphyrin derivatives controlled by fused benzo rings. Chem A Eur J 10:4422–4435

    CAS  Google Scholar 

  27. Linstead RP, Whalley M (1952) Conjugated macrocycles. Part XXI tetrazaporphin and its metallic derivatives. J Chem Soc. https://doi.org/10.1039/jr9520004839

    Google Scholar 

  28. Tillo DT, Mlynarczyk L, Popenda B, Wicher M, Kryjewski W, Szczolko S, Jurga J, Mielcarek M, Gdaniec T, Tykarska E (2017) Synthesis and singlet oxygen generation of pyrazinoporphyrazines containing dendrimeric aryl substituents. New J Chem 41:3586–3594

    CAS  Google Scholar 

  29. Roy S, Narang BK, Rastogi SK, Rawal RK (2015) A novel multiple tyrosine-kinase targeted agent to explore the future perspectives of anti-angiogenic therapy for the treatment of multiple solid tumors: cabozantinib. Anti Cancer Agent Med Chem 15:37–47

    CAS  Google Scholar 

  30. Cui JJ, Tran-Dube M, Shen H, Nambu M et al (2011) Structure based drug design of crizotinib (PF-02341066), a potent and selective dual inhibitor of mesenchymal-epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK). J Med Chem 54:6342–6363

    CAS  Google Scholar 

  31. Zhao F, Zhang J, Zhang L, Hao Y, Shi C, Xia G, Yu J, Liu Y (2016) Discovery and optimization of a series of imidazo[4,5-b]pyrazine derivatives as highly potent and exquisitely selective inhibitors of the mesenchymal-epithelial transition factor (c-Met) protein kinase. Bioorg Med Chem 24:4281–4290

    CAS  Google Scholar 

  32. Andrews MJI, Clase JA, Bar G, Tricarico G, Edwards PJ, Brys R, Chambers M, Schmidt W, MacLeod A, Hirst K, Allen V, Birault V, Le J, Harris J, Self A, Nash K, Dixon G (2012) Discovery of a series of imidazopyrazine small molecule inhibitors of the kinase MAPKAPK5 that show activity using in vitro and in vivo models of rheumatoid arthritis. Bioorg Med Chem Lett 22:2266–2270

    CAS  Google Scholar 

  33. Goel R, Luxami V, Paul K (2014) Palladium catalyzed novel monoarylation and symmetrical/unsymmetrical diarylation of imidazo[1,2-a]pyrazines and their in vitro anticancer activities. RSC Adv 4:9885–9892

    CAS  Google Scholar 

  34. Touster O (2011) The nitrosation of aliphatic carbon atoms. Org React 7(6):327–377

    Google Scholar 

  35. Madhavi L, Sadasivam V, Sivasankar B (2007) A highly selective synthesis of pyrazine from ethylenediamine on copper oxide/copper chromite catalysts. Catal Commun 8:1070–1073

    Google Scholar 

  36. Krishna V, Naresh G, Kumar VV, Sarkari R, Padmasri AH, Venugopal A (2016) Synthesis of 2,6-dimethylpyrazine by dehydrocyclization of aqueous glycerol and 1,2-propanediamine over CuCrO catalyst: rationalization of active sites by pyridine and formic acid adsorbed IR studies. Appl Catal B 193:58–66

    CAS  Google Scholar 

  37. Sarkari R, Anjaneyulu C, Krishna V, Kishore R, Sudhakar M, Venugopal A (2011) Vapor phase synthesis of methylpyrazine using aqueous glycerol and ethylenediamine over ZnCr2O4 catalyst: Elucidation of reaction mechanism. Catal Commun 12(12):1067–1070

    CAS  Google Scholar 

  38. Venugopal AV, Sarkari R, Anjaneyulu C, Vankudoth K, Mandari KK (2012) Synthesize 2-methylpyrazine using aqueous glycerol and ethylenediamine over zinc oxide–zinc chromite catalysts: structure–activity relationship. Appl Catal A 441–442:108–118

    Google Scholar 

  39. Elmaaty TA, Castle LW (2005) Facile regiocontrolled synthesis of trialkyl-substituted pyrazines. Org Lett 7(24):5529–5530

    CAS  Google Scholar 

  40. Douglass F, Taber DF, DeMatteo PW, Taluskie KV (2006) Synthesis of symmetrical and unsymmetrical pyrazines. J Org Chem 72:1492–1494

    Google Scholar 

  41. Jeong JU, Sutton SC, Kim SH, Fuchs PL (1995) Biomimetic total syntheses of (+)cephalostatin 7, (+)-cephalostatin 12, and (+)-ritterazine K. J Am Chem Soc 117:10157

    CAS  Google Scholar 

  42. Stetin C, de Jeso B, Pommier JC (1982) Imine synthesis in strictly neutral conditions. Synth Commun 25(3):369–378

    Google Scholar 

  43. Aparicio D, Attanasi OA, Filippone P, Ignacio R, Lillini S, Mantellini F, Palacios F, de los Santos JM (2006) Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1,3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions. J Org Chem 71:5897–5905

    CAS  Google Scholar 

  44. Nie Q, Yao F, Yi F, Cai M (2017) A heterogeneous gold(I)-catalyzed cascade annulation of aldehydes with propargylamine leading to 3-substituted 2,5-dimethylpyrazines. J Organomet Chem 846:343–350

    CAS  Google Scholar 

  45. Li X, Deng S, Fu H (2011) Three pyrazine derivatives as corrosion inhibitors for steel in 1.0 M H2SO4 solution. Corros Sci 53:3241–3247

    CAS  Google Scholar 

  46. Saha S, Hens A, Chowdhury AR, Lohar A, Murmu NC, Banerjee P (2014) Molecular dynamics and density functional theory study on corrosion inhibitory action of three substituted pyrazine derivatives on steel surface. Can Chem Trans 2(4):489–503

    Google Scholar 

  47. Obot IB, Gasem ZM (2014) Theoretical evaluation of corrosion inhibition performance of some pyrazine derivatives. Corros Sci 83:359–366

    CAS  Google Scholar 

  48. Kissi M, Bouklah M, Hammouti B, Benkaddour M (2006) Establishment of equivalent circuits from electrochemical impedance spectroscopy study of corrosion inhibition of steel by pyrazine in sulphuric acidic solution. Appl Surf Sci 252:4190–4197

    CAS  Google Scholar 

  49. Farag AA, Ali AT (2015) The enhancing of 2-pyrazinecarboxamide inhibition effect on the acid corrosion of carbon steel in presence of iodide ions. J Ind Eng Chem 21:627–634

    CAS  Google Scholar 

  50. Saranya J, Sounthari P, Parameswari K, Chitra S (2016) Acenaphtho[1,2-b]quinoxaline and acenaphtho[1,2-b]pyrazine as corrosion inhibitors for mild steel in acid medium. Measurement 77:175–186

    Google Scholar 

  51. Bouklah M, Attayibat A, Kertit S, Ramdani A, Hammouti B (2005) A pyrazine derivative as corrosion inhibitor for steel in sulphuric acid solution. Appl Surf Sci 242:399–406

    CAS  Google Scholar 

  52. Deng S, Li X, Fu H (2011) Two pyrazine derivatives as inhibitors of the cold rolled steel corrosion in hydrochloric acid solution. Corros Sci 53:822–828

    CAS  Google Scholar 

  53. Hjouji MY, Djedid M, Elmsellem H, Kandri Rodi Y, Ouzidan Y, Chahdi FQ, Sebbar NK, Essassi EM, Abdel-Rahman I, Hammouti B (2016) Corrosion Inhibition of mild steel in hydrochloric acid solution by pyrido[2,3-b]pyrazine derivative: electrochemical and theoretical evaluation. J Mater Environ Sci 7(4):1425–1435

    CAS  Google Scholar 

  54. Mohammed Abdulwahed JA, Attia A, Elsayad MR, Eldesoky AM (2014) Inhibitive effect of azine and diazine derivatives on the corrosion of cyclic stressed 316l SS in acidic media. Int J Sci Eng Res 5(11):342–356

    Google Scholar 

  55. Massoud AA, Hefnawy A, Langer V, Khatab MA, Ohrstrom L, Abu-Youssef MAM (2009) Synthesis, X-ray structure and anti-corrosion activity of two silver(I)pyrazino complexes. Polyhedron 28:2794–2802

    CAS  Google Scholar 

  56. Hamdy A, El-Gendy S (2013) Thermodynamic, adsorption and electrochemical studies for corrosion inhibition of carbon steel by henna extract in acid medium. Egypt J Pet 22:17–25

    Google Scholar 

  57. Zhang S, Li H, Wang L, Liu D, Ping E, Zou P, Ma T, Li N (2016) New pyrazine derivatives as efficient inhibitors on mild steel corrosion in hydrochloric medium. Chem Eng Trans 55:289–294

    Google Scholar 

  58. Onyeachu BI, Peng X, Oguzie EE, Ogukwe CE, Digbo I (2015) Characterizing the electrochemical corrosion behaviour of a Ni-28 wt%Al composite coating in 3.5% NaCl solution. Port Electrochim Acta 33:69–83

    CAS  Google Scholar 

  59. Esther Rani JRB, Jeyaraj T (2012) Inhibition of the corrosion of aluminium in alkaline medium by 1-(phenyl)-3-(2-hydroxy phenyl)-propenone in the presence of tetrabutylammonium bromide. Der Chem Sin 3:1358–1368

    Google Scholar 

  60. Zheludkevich ML, Yasakau KA, Poznyak SK, Ferreira MGS (2005) Triazole and thiazole derivatives as corrosion inhibitors for AA2024 aluminium alloy. Corros Sci 47:3368–3383

    CAS  Google Scholar 

  61. Abdallah M, Sobhi M, Al-Tass HM (2016) Corrosion inhibition of aluminum in hydrochloric acid by pyrazinamide derivatives. J Mol Liq 223:1143–1150

    CAS  Google Scholar 

  62. Cao X, Jahazi M, Immarigeon J, Wallace W (2006) A review of laser welding techniques for magnesium alloys. J Mater Process Technol 171:188–204

    CAS  Google Scholar 

  63. Staiger M, Pietak A, Huadmai J, Dias G (2006) Magnesium and its alloys as orthopedic biomaterials: a review. Biomaterials 27:1728–1734

    CAS  Google Scholar 

  64. He SM, Zheng XQ, Peng LM, Gao F, Nie JF, Ding WJ (2007) Microstructure and strengthening mechanism of high strength Mg–10Gd–2Y–0.5Zr alloy. J Alloys Compd 427(1):316–323

    CAS  Google Scholar 

  65. He SM, Zheng XQ, Peng LM, Gao F, Nie JF, Ding WJ (2006) Microstructure evolution in a Mg-15Gd-0.5Zr alloy during isothermal aging at 250 °C. J Alloys Compd 421(1):309–313

    CAS  Google Scholar 

  66. Zhang J, Zhang Z (2004) Magnesium alloys and their applications. Chemical Industry Press of China, Beijing. ISBN 7-5025-5709-9

    Google Scholar 

  67. Gary J, Luan B (2002) Protective coating on magnesium and its alloys—a critical review. J Alloys Compd 336:88–113

    Google Scholar 

  68. Slavcheva E, Schmitt G (2002) Screening of new corrosion inhibitors via electrochemical noise analysis. Mater Corros 53:647–655

    CAS  Google Scholar 

  69. Hu J, Huang D, Zhang G, Song GL, Guo X (2012) Research on the inhibition mechanism of tetraphenylporphyrin on AZ91D magnesium alloy. Corros Sci 63:367–378

    CAS  Google Scholar 

  70. Huang D, Tu Y, Song G, Guo X (2013) Inhibition effects of pyrazine and piperazine on the corrosion of Mg–10Gd–3Y–0.5Zr alloy in an ethylene glycol solution. Am J Anal Chem 4:36–38

    Google Scholar 

  71. Sahin M, Bilgic S, Yilmaz H (2002) The inhibition effects of some cyclic nitrogen compounds on the corrosion of the steel in NaCl mediums. Appl Surf Sci 195:1–7

    CAS  Google Scholar 

  72. de Damborenea J, Bastidas JM, Vazquez AJ (1997) Adsorption and inhibitive properties of four primary aliphatic amines on mild steel in 2 M hydrochloric acid. Electrochim Acta 42(3):455–459

    Google Scholar 

  73. Gece G, Bilgic S (2009) Quantum chemical study of some cyclic nitrogen compounds as corrosion inhibitors of steel in NaCl media. Corros Sci 51(8):1876–1878

    CAS  Google Scholar 

  74. Sahin M, Gece G, Karci SB (2008) Experimental and theoretical study of the effect of some heterocyclic compounds on the corrosion of low carbon steel in 3.5% NaCl medium. J Appl Electrochem 38(6):809–815

    CAS  Google Scholar 

  75. Finsgar M, Fassbender S, Hirth S, Milosev I (2009) Electrochemical and XPS study of polyethyleneimines of different molecular sizes as corrosion inhibitors for AISI 430 stainless steel in near-neutral chloride media. Mater Chem Phys 116(1):198–206

    CAS  Google Scholar 

  76. Wahyuningrum D, Achmad S, Maolana Syah Y, Ariwahjoedi B (2008) The synthesis of imidazoline derivative compounds as corrosion inhibitor towards carbon steel in 1% NaCl solution. ITB J Sci 40(1):33–48

    Google Scholar 

  77. Mubarak MS, Peters DG (2001) Survey of the electrochemical behavior of chlorinated pyrazines, quinoxalines, and pyridazines at carbon and mercury cathodes. J Electroanal Chem 507:110–117

    CAS  Google Scholar 

Download references

Acknowledgements

The authors would like to acknowledge the support received from King Abdulaziz City for Science and Technology (KACST) for funding this work under the National Science Technology Plan (NSTIP) Grant No. 14-ADV2448-04. Also, the support provided by the Deanship of Scientific Research (DSR) and the Center of Research Excellence in Corrosion (CORE-C), at King Fahd University of Petroleum and Minerals (KFUPM), is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. B. Obot.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Obot, I.B., Onyeachu, I.B. & Umoren, S.A. Pyrazines as Potential Corrosion Inhibitors for Industrial Metals and Alloys: A Review. J Bio Tribo Corros 4, 18 (2018). https://doi.org/10.1007/s40735-018-0135-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s40735-018-0135-2

Keywords

Navigation