Synthesis of New Dithiocarbamate Derivative Reagent for Micro Extraction and Determination of Iron(II) Ion in Aqueous Solution

https://doi.org/10.22146/ijc.87422

Ivan Malik Shaker(1), Ahmed Fadhil Khudhair(2*), Hayder Hamied Mihsen(3)

(1) Department of Chemistry, College of Science, University of Kerbala, Karbala 56001, Iraq
(2) Department of Chemistry, College of Science, University of Kerbala, Karbala 56001, Iraq
(3) Department of Chemistry, College of Science, University of Kerbala, Karbala 56001, Iraq
(*) Corresponding Author

Abstract


The new reagent N-methyl-N-((((4-chlorophenyl)diazenyl)thio)carbonothioyl)aniline (L) was synthesized via the reaction of sodium N-methyl-N-phenyldithiocarbamate with 4-chlorobenzenediazonium salt. The reagent was identified with many techniques, such as CHNS elemental analysis, UV-vis spectroscopy, FTIR spectroscopy, mass spectroscopy, 1H-NMR, and 13C-NMR spectroscopy. The Fe(II) ion was utilized to create a metal complex by reacting 2 mol of reagent with 1 mol of iron(II) chloride. Two approaches that were utilized for M:L ratio determination are mole ratio and Job methods. All of these refer to the 1:2 ratio for the complex. The solid complex was prepared and identified with the previous techniques, and additional electrical molar conductivity, and magnetic susceptibility measurements. A tetrahedral structure for the prepared complex was suggested based on spectroscopic measurements and elemental analysis results. Cloud point extraction was created for the preconcentration and separation of Fe(II) in drug samples by forming a rich phase using Triton X-114 at 80 °C temperature and pH 5 measurements utilizing flame atomic absorption spectroscopy and UV-vis spectrophotometer at λmax 635 nm. The calibration curve of Fe(II) was linear in the extent of 0.2–1.0 μg/mL with r2 of 0.996. The detection limit and quantification are 0.0504 and 0.1530 μg/mL.


Keywords


dithiocarbamite derivative; pre-concentration; cloud point extraction

Full Text:

Full Text PDF


References

[1] Adeyemi, J.O., Saibu, G.M., Olasunkanmi, L.O., Fadaka, A.O., Meyer, M., Sibuyi, N.R.S., Onwudiwe, D.C., and Oyedeji, A.O., 2021, Synthesis, computational and biological studies of alkyltin(IV) N-methyl-N-hydroxyethyl dithiocarbamate complexes, Heliyon, 7 (8),‏ e07693.

[2] Abdullah, T.B., Behjatmanesh-Ardakani, R., Faihan, A.S., Jirjes, H.M., Abou-Krisha, M.M., Yousef, T.A., Kenawy, S.H., and Al-Janabi, A.S.M., 2023, Cd(II) and Pd(II) mixed ligand complexes of dithiocarbamate and tertiary phosphine ligands—Spectroscopic, anti-microbial, and computational studies, Molecules, 28 (5), 2305.‏

[3] Odularu, A.T., and Ajibade, P.A., 2019, Dithiocarbamates: Challenges, control, and approaches to excellent yield, characterization, and their biological applications, Bioinorg. Chem. Appl., 2019, 8260496.

[4] Kareem, A., Nami, S.A., Khan, M.S., Bhat, S.A., Mirza, A.U., Laxmi, L., and Nishat, N., 2019, Self-assembled transition metal dithiocarbamates of pyridine-3-carboxamide: Synthesis, spectral characterization, thermal and biological studies, New J. Chem., 43 (11), 4413–4424.

[5] Ali, W.A., Mihsen, H.H., and Guzar, S.H., 2023, Novel derivative for dithiocarbamite containing a new sulphur-azo linkage and its complexes with Sn(II), Sn(IV), Co(II), Ni(II) and Cu(II) ions; Synthesis, characterization and antibacterial Activity, Al-Bahir J. Eng. Pure Sci., 2 (1), 18–25.

[6] Awang, N., Kamaludin, N.F., Baba, I., Chan, K.M., Rajab, N.F., and Hamid, A., 2016, Synthesis, characterization, and antitumor activity of new organotin(IV) methoxyethyldithiocarbamate complexes, Orient. J. Chem., 32 (1), 101–107.

[7] Saridal, K., and Ulusoy, H.İ., 2019, A simple methodology based on cloud point extraction prior to HPLC-PDA analysis for tetracycline residues in food samples, Microchem. J., 150, 104170.

[8] Akl, Z.F., and Hegazy, M.A., 2020, Selective cloud point extraction of thorium(IV) using tetraazonium based ionic liquid, J. Environ. Chem. Eng., 8 (5), 104185.

[9] Hamran, B.N., and Khudhair, A.F., 2020, Micellar determination of amoxicillin in the pharmaceutical compounds by using cloud point extraction, Res. J. Pharm. Technol., 13 (2), 732–741.

[10] Zheng, H., Hong, J., Luo, X., Li, S., Wang, M., Yang, B., and Wang, M., 2019, Combination of sequential cloud point extraction and hydride generation atomic fluorescence spectrometry for preconcentration and determination of inorganic and methyl mercury in water samples, Microchem. J., 145, 806–812.

[11] Abood, N.K., Hassan, M.J.M., and Al-Da’amy, M.A., 2019, Determination of cefixime using batch, cloud point extraction and flow injection as new spectrophotometric methods, Al-Mustansiriyah J. Sci., 30 (3), 28–37.‏

[12] Xie, M., Liu, W., Hao, X., Jiang, X., Zhong, Y., Liu, T., and Wang, M., 2021, Cloud point extraction combined with flame atomic absorption spectrometry for the determination of copper, iron and zinc using 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol-tetraphenylborate ion-pairing agent, Chem. Pap., 75 (11), 5849–5859.

[13] López-García, I., Marín-Hernández, J.J., and Hernández-Córdoba, M., 2018, Graphite furnace atomic absorption spectrometric determination of vanadium after cloud point extraction in the presence of graphene oxide, Spectrochim. Acta, Part B, 143, 42–47.

[14] Al-ward, H.S., Al-Abachi, M.Q., and Ahmed, M.R., 2023, Spectrophotometric analysis of vancomycin hydrochloride in pure and pharmaceutical injections via batch and cloud point extraction techniques, Baghdad Sci. J., 20 (2), 0245.

[15] Hamran, B.N., and Khudhair, A.F., 2022, Micro analysis ranitidine in pharmaceutical formation using CPE method coupling with spectrophotometric method, AIP Conf. Proc., 2547 (1), 040013.

[16] Najm, A.A.H., and Abbas, A.S., 2023, Simple cloud point extraction-spectrophotometric for the determination for cobalt(II) using-3-anilino-1-phenylimino-thiourea, HIV Nurs., 23 (1), 688–692.‏

[17] Abbas, A.S., Al-Khafaji, Y., and Al-Khafaji, H.A.H., 2018, Cloud point extraction as a procedure of separation and pre-concentration for cupper(II) determination using spectrofluorometric techniques, J. Pharm. Sci. Res., 10 (7), 1748–1752.

[18] Luo, X., Zheng, H., Zhang, Z., Wang, M., Yang, B., Huang, L., and Wang, M., 2018, Cloud point extraction for simultaneous determination of 12 phenolic compounds by high performance liquid chromatography with fluorescence detection, Microchem. J., 137, 148–154.‏

[19] Abbas, S.H., 2017, Synthesis, characterization and biological activity of some nickel(II) mixed ligands complexes of dithiocarbamate and 1,10-phenanthroline, Eur. J. Chem., 8 (4), 367–370.‏

[20] Halls, D.J., 1969, The properties of dithiocarbamates: A review, Microchim. Acta, 57 (1), 62–77.

[21] Kaul, B.B., and Pandeya, K.B., 1979, N-monoaryldithiocarbamate cobalt(III) complexes(1), Transition Met. Chem., 4 (2), 112–114.

[22] Prashantha, A.G., Keshavayya, J., and Shoukat Ali, R.A., 2021, Synthesis and studies on novel toluic acid-based azo dyes, Rasayan J. Chem., 14 (3), 1635–1642.

[23] Mahato, M., Mukherji, S., Van Hecke, K., Harms, K., Ghosh, A., and Nayek, H.P., 2017, Mononuclear homoleptic organotin(IV) dithiocarbamates: Syntheses, structures and antimicrobial activities, J. Organomet. Chem., 853, 27–34.

[24] Yang, H., Li, L., Song, Y., Hou, H., and Fan, Y., 2008, Syntheses and characterization of ferrocenylthiocarboxylate-containing coordination compounds for nonlinear optics‏, J. Organomet. Chem., 693 (15), 2624–2630.

[25] Adeyemi, J.O., Onwudiwe, D.C., and Singh, M., 2019, Synthesis, characterization, and cytotoxicity study of organotin(IV) complexes involving different dithiocarbamate groups, J. Mol. Struct., 1179, 366–375.

[26] Onwudiwe, D.C., Nthwane, Y.B., Ekennia, A.C., and Hosten, E., 2016, Synthesis, characterization and antimicrobial properties of some mixed ligand complexes of Zn(II) dithiocarbamate with different N-donor ligands, Inorg. Chim. Acta, 447 (2), 134–141.

[27] Onwudiwe, D.C., and Ajibade, P.A., 2011, Synthesis, characterization and thermal studies of Zn(II), Cd(II) and Hg(II) complexes of N-Methyl-N-phenyldithiocarbamate: The single crystal structure of [(C6H5)(CH3)NCS2]4Hg2, Int. J. Mol. Sci., 12 (3), 1964–1978.

[28] Lever, A.B.P., 1984, Inorganic Electronic Spectroscopy, 2nd Ed., Elsevier, Amsterdam, Netherlands.

[29] Al-Hmedawi, H.H., and Abdulkhaleq, R., 2015, Preparation and spectral study of Co(II), Ni(II), Cu(II), Pd(II) and Pt(IV) complexes containing N2 donor atoms abstract, Q. Adjud. J. Nat. Eng. Res. Stud., 2 (3-4), 48–67.

[30] Mihsen, H.H., Abass, S.K., Abed Alhasan, M.T., Hassan, Z.M., and Abass, A.K., 2020, Synthesis, characterization and antimicrobial activities of mixed ligand complexes of Fe(II), Co(II), Ni(II) and Cu(II) ions derived from imine of benzidine and o-phenylenediammine, Iraqi J. Sci., 61 (11), 2762–2775.

[31] Filik, H., and Giray, D., 2012, Cloud point extraction for speciation of iron in beer samples by spectrophotometry, Food Chem., 130 (1), 209–213.‏



DOI: https://doi.org/10.22146/ijc.87422

Article Metrics

Abstract views : 211 | views : 133


Copyright (c) 2024 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.