Abstract
Herein this work, summarize the behavior of the electrode reaction of some arylazomethine-1,2,3-triazole derivatives via convolutive sweep voltammetry, chronoamperometry and differential pulse polarography techniques in Britton Robinson universal aqueous buffer series with pH in the range of 2.4–11.8, at mercury electrode (HMDE). The evaluation of the important kinetics criteria of arylazomethine-1,2,3-triazole derivatives was performed experimentally in Britton Robinson universal buffer solutions. The electrons which participate in the electrode reaction of arylazomethine-triazole derivatives were calculated using controlled potential coulometry. Theoretical cyclic sweep voltammograms were generated via software of digital simulation for testing the accuracy of the experimental chemical and electrochemical criteria. The good comparison between the generated and experimental cyclic sweep voltammograms confirms the accuracy of the electrochemical parameters and the proposed electrode mechanism.
Graphical Abstract
A good agreement between the theoretical voltammograms and the experimental one of EqCirr model of the 3-((1H-1,2,3-triazol-4-ylimino)methyl)phenol derivative (1) at pH 3.2 and a scan rate of 1000 mVs-1 is shown in the following figure. The obtained theoretical and experimental chemical and electrochemical parameters confirm the accuracy of the proposed mechanism.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Al-bishri HM, El-Hallag IS, El-Mossalamy EH (2011) Electrochemical properties of closo-2,3 dicarbaundecaborane in dichloromethane at a glassy carbon electrode using potentiostatic, galvanostatic and digital simulation methods. J New Mat Electrochem Sys 14:51–57. https://doi.org/10.14447/jnmes.v14i1.130
Alford PD, Goto M, Oldham KB (1977) Shapes of derivative neopolarograms. J Electroanal Chem 85:1–15. https://doi.org/10.1016/s0022-0728(77),80148-4
Al-Owais A, El-Hallag IS (2015) Voltammetric studies of anthracen-9-ylmethylene-(3,4-dimethyl-isoxazol-5-yl)-amine compound at platinum electrode. J New Mat Electrochem Sys 18:177–181. https://doi.org/10.14447/jnmes.v18i3.366
Al-Owais AA, El-Hallag IS (2016) Electrochemical behaviour of copper(II) at a hanging mercury drop electrode. ScienceAsia 42:114–120. https://doi.org/10.2306/scienceasia1513-1874.2016.42.114
Al-Owais AA, El-Hallag IS, Al-Harbi LM, El-Mossalamy EH, Qar HA (2014) Electrochemical properties of charge transfer complexes of 4,4′-bipyridine with benzoquinone derivatives. J New Mat for Electrochem Sys 17:17–21. https://doi.org/10.14447/jnmes.v17i1.438
Bard AJ, Faulkner LR (1982) In electrochemical methods fundamentals and applications. Wiley, New York, pp 218–219
Blagg A, Carr SW, Cooper GR, Dobson ID, Gill JB, Goodal DC, Shaw BL, Taylor N, Boddington T (1985) A mechanistic study on complexes of type mer-[Cr(CO)3(η2-L–L)(σ-L–L)](where L–L = Ph2PCH2-PPh2,Ph2PNHPPh2, or Ph2PNMePPh2) using spectroscopic and convolutive electrochemical techniques. J Chem Soc Dalton Trans. https://doi.org/10.1039/dt9850001213
Deeth RJ, Langford SA (1995) Metaldinitrogen a- and z-bonding roles in [Fe(dmpe),H(NJ] [Fe(depe),(NJ] and trans-[V(dmpe),(N,),]-(dmpe = Me,PCH,CH,-PMe, depe = Et,PCH,CH,PEt,). J Chem Soc Dalton Trans 1:1–6. https://doi.org/10.1039/dt99500fp001
Delahay P (1953) Theory of irreversible waves in oscillographic polarography. J Am Chem Soc 75:1190–1196. https://doi.org/10.1021/ja01101a054
El-Hallag IS (1991) Electrochemical studies of some metalloborane and carbonyl phosphine complexes in nonaqueous medium. PhD Thesis, Tanta University, Egypt
El-Hallag IS, El-Mossalamy EH, Asiri AM (2012) Electrochemical investigation of antibacterial laser dye compound in 1,2-dichloroethane at a platinum electrode. Iran J Chem Chem Eng 31:9–18
Ferrarini PL, Mor C, Badawneh M, Manera C, Saccomanni G, Calderone V, Scatizzi R, Barili PL (1998) Stereoselective synthesis and β-blocking activity of substituted (E)- and (Z)-4(1H)-[1-(3-alky-lamino-2-hydroxypropyl)oximino]-2,3-dihydro-1,8-naphthyridine. Potential antihypertensive agents. Part VI. J Med Chem 17:955–963. https://doi.org/10.1016/S0223-5234(97),89639-0
Fuchigami T, Sano M, Lio K (1994) Electrolytic partial fluorination of organic compounds. Part IX. Selective anodic monofluorination of hydrazones. J Electroanal Chem 369:255–258. https://doi.org/10.1016/0022-0728(94),87107-8
Ghanem MA, El-Hallag IS (2015) Electrodeposition and characterization of mesoporous nanostructured cobalt films using brij78 templated. J New Mat Electrochem Sys 18:121–181. https://doi.org/10.14447/jnmes.v18i3.364
Ghanem MA, El-Hallag IS, Mayouf AM (2017) Electrochemical behavior and convoluted voltammetry of carbon nanotubes modified with anthraquinone. J New Mat Electrochem Sys 20:25–30. https://doi.org/10.14447/jnmes.v20i1.291
Gopalakrishnan M, Sureshkumar P, Thanusu J, Kanagarajan V (2008) Unusual Formation of N-hydroxy-3,3- dimethyl-2,6-diarylpiperidin-4-one and its thiosemicarbazide derivative-synthesis and antimicrobial activity. J Koren Chem Soc 52:503–510. https://doi.org/10.5012/jkcs.2008.52.5.503
Huntley AC, Walter RMJ (1990) Quantitative determination of skin thickness in diabetes mellitus: relationship to disease parameters. J Med 21:257–264
Imbeaux JC, Saveant JM (1970) Linear sweep voltammetry. Effect of uncompensated cell resistance and double layer charging on polarization curves. J Electroanal Chem 28:325–338. https://doi.org/10.1016/S0022-0728(70),80127-9
Jain R, Padamaja P, Gupta S (1997) Electrochemical investigation of some potential antibacterials II. Can J Chem 75:567–574. https://doi.org/10.1139/v97
Kane JM, Dudley MW, Sorenson SM, Miller FP (1988) 2,4-Dihydro-3H-1,2,4-triazole-3-thiones as potential—antidepressant agents. J Med Chem 31:1253–1258. https://doi.org/10.1021/jm00401a031
Kausar A, Zulfiqar S, Ahmad Z, Sarwa MI (2010) Novel processable and heat resistant poly- (phenyl- thiourea azomethine imides): synthesis and characterization. Polym Degrad Stab 95:1826–1833. https://doi.org/10.1016/j.polymdegradstab.20
Kerneghan PA, Halperin SD, Bryce DL, Maly KE (2011) Postsynthetic modification of an imine-based -microporous organic network. Can J Chem 89:577–582. https://doi.org/10.1139/v11-014
Koltheff LM, Lingance JJ (1952) Polarography. Interscience, New York, p 319
Lallan M, Ajay KY (2000) Synthesis, spectroscopic, electrochemical and luminescence studies of ruthenium (II) polypyridyls containing multifunctionalized 1,2,4-triazole as co-ligand. Proc Indian Acad Sci 112:449–458. https://doi.org/10.1007/BF02704350
Lund H (1959) Electroörganic preparations. VI. reduction of compounds containing the azomethine group. Acta Chem Scan 13:249–267. https://doi.org/10.3891/acta.chem.scand.13-0249
Meites L (1965) In polarographic techniques, 4th edn. Interscience Publishers Inc, New York, pp 240–248
Messeder JC, Tinovo LW, Souza EM, Rita RS, De Castro SL (1995) Aromatic guanylhydra-zones: synthesis, structural studies and in vitro activity against Trypanosoma cruzi. Bioorg Med Chem Lett 24:3079–3084. https://doi.org/10.1016/0960-894X(95)0054
Neudeck A, Dittrich J (1989) Determination of the kinetic parameters of the charge transfer and chemical follow-up reaction for EC, DISP1 and ECE mechanisms by means of cyclic voltamm-etry. J Electroanal Chem 264:91–119. https://doi.org/10.1016/0022-0728(89),80150-0
Nichlson RS (1965) Theory and application of cyclic voltammetry for measurement of electrode reaction kinetics. Anal Chem 37:1351–1355. https://doi.org/10.1021/ac60230a016
Nicholson RS, Shain I (1964) Theory of stationary electrode polarography single scan and cyclic methods applied to reversible, irreversible, and kinetic systems. Anal Chem 36:706–723. https://doi.org/10.1021/ac60210a007
Obaid AY, El-Mossalamy EH, Al-Thabaiti SA, El-Hallag IS, Hermas AA, Asiri AM (2014) Electrodeposition and characterization of polyaniline on stainless steel surface via cyclic voltammetry and SEM in aqueous acidic solutions. Int J Electrochem Sci 9:1003–1015
Oldham KB, Zoski GD (1983) Semiintegral electroanalysis with discrimination against charging current. J Electroanal Chem 145:265–278. https://doi.org/10.1016/S0022-0728(83),80086-2
Pandey P, Katsoulidis AP, Eryazici I, Wu Y, Kanatzidis MG, Nguyen ST (2010) Imine-linked microporous polymer organic frameworks. Chem Mater 22:4974–4979. https://doi.org/10.1021/cm101157w
Pattakaran RLR, Burkanudeen AR (2012) Synthesis and characterization of epoxy-containing schiff-base and phenylthiourea groups for improved thermal conductivity. Polym Plast Technol 51:140–145. https://doi.org/10.1080/03602559.2011.618165
Ram VJ, Dube V, Pieters IAC, Vlietinck AJ (1989) Chemotherapeutic agents. IX. Synthesis and pesticidal-activities of bis[4aryl/alkyl1, 2, 4-triazoline-5-thione-3-yl]alkanes and 1 -Aryl/alkyl-3-[4-(4-aryl/alkyl-1, 2, -4-triazoline-5-thione-3-yl)phenyl]thiourea and related compounds. J Heterocycl Chem 26:625–628. https://doi.org/10.1002/jhet.5570260321
Raman N, Dhaveethu Raja J, Sakthivel JA (2007) Synthesis, spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies. J Chem Sci 119:303–310
Sadler JL, Bard AJ (1968) Electrochemical reduction of aromatic azo compounds. J Am Chem Soc 90:1979–1989. https://doi.org/10.1021/ja01010a010
Saveant JM, Tessier D (1975) Convolution potential sweep voltammetry vs. determination of charge transfer kinetics deviating from the Butler-Volmer behaviour. Electranal Chem 65:57–66. https://doi.org/10.1016/0368-1874(75),85105-7
Sek D, Grabiec E, Janeczek H, Jarzabek B, Kaczmarczyk B, Domanski M, Iwan A (2010) Structure properties relationship of linear and star-shaped imines with triphenylamine moieties as hole-transporting-materials. Opt Mater 32:1514–1524. https://doi.org/10.1016/2Fj.optmat.2010.06.013
Sung K, Lee AR (1992) Synthesis of [(4,5-disubstituted-4H-1,2,4-triazol-3-yl)thio]alkanoic acids and their analogues as possible antiinflammatory agents. J Heterocycl Chem 92:1101–1109. https://doi.org/10.1002/jhet.5570290512
Temerk YM, Ghoneim MM, Maghrabi JY (1978) Spectrophotometric study of some arylidene derivatives of benzoic and salicylic acid hydrazides in buffer solutions. J Parkt Chem 320:1029–1035. https://doi.org/10.1002/prac.19783200620
Uribe-Romo FJ, Hunt JR, Furukawa H, Klöck C, O’Keeffe M, Yaghi OM (2009) Crystalline covalent organic frameworks with hydrazone linkages. J Am Chem Soc 131:4570–4571. https://doi.org/10.1021/ja8096256
Uribe-Romo FJ, Doonan CJ, Furukawa H, Oisaki K, Yaghi OM (2011) Crystalline covalent organic frame- works with hydrazone linkages. J Am Chem Soc 133:11478–11481. https://doi.org/10.1021/ja204728y
Virtoneon AI, Heitala PK (1960) Precursors of benzoxazoline in rye plants I precursor II, the aglucone. Acta Chem Scand 14:499–502. https://doi.org/10.3891/acta.chem.scand.14-0499
Woodard FE, Goodinand RD, Kinlen PJ (1984) Kinetic convolution analysis of cyclic voltammetric data. Anal Chem 56:1920–1923. https://doi.org/10.1021/ac00275a036
Zhang M, Gorski W (2005) Electrochemical sensing based on redox mediation at carbon nanotubes. Anal Chem 77:3960–3965. https://doi.org/10.1021/ac050059u
Zhang XH, Huang LH, Chen S, Qi GR (2007) Improvement of thermal properties and flame retardancy of epoxy-amine thermosets by introducing bisphenol containing azomethine moiety. Express Polym Lett 1:326–332. https://doi.org/10.3144/expresspolymlett.2007.46
Zuman P (1969) The elucidation of organic electrode processes. Academic Press, New York, p 115
Acknowledgements
This project was supported by King Saud University, Deanship of Scientific Research, College of Science, Research Center.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Al Owais, A.A., El-Hallag, I.S. Electrode behavior of some triazole derivatives using convolutive voltammetry, chronoamperometry and differential pulse polarography techniques. Chem. Pap. 73, 2353–2362 (2019). https://doi.org/10.1007/s11696-019-00788-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-019-00788-9