Synthesis and analytical applications of thiosemicarbazide derivative

Year 2021, , 59 - 63, 30.12.2021

Abidin Gümrükçüoğlu , Olcay Bekircan

https://doi.org/10.51435/turkjac.1030232

Cited By: 1

Abstract

1-(4-tert-butylphenyl)4-(4-trifluoromethylphenyl)carbonylthiosemicarbazide (OBS) and was synthesized by reaction of 4-tert-Butylbenzoic hydrazide with 4-(trifluoromethyl)phenylisothiocyanate. The influence of many metal cations on the spectroscopic properties of the synthesized compound was investigated in dmso-water (1:1) by means of emission spectrometry.The influence of a series of metal ions including Cu2+,Co2+ , Al3+,Cr3+,Fe3+, Pb2+, Ni2+, Cd2+, Zn2+,Ag+ , Ba2+ , Mo3+, Se,Ca2+,Sn4+,Sb3+,Na+, K+,Li+,Sc3+, Sr2+, As3+, Be2+ and Mg2+on the spectroscopic properties of the ligand was investigated by means of emission spectrometry.The compounds were selectively complexed with Fe3+among many metal ions. The complex stoichiometry and the stability constant were determined by fluorimetric measurements. The ligand having thiosemicarbazide (OBS) showed sensitivity for Fe3+ ion with a linear range between 0.5 and 5.5 mg/L. The new method was applied in the determination of iron in the the sandy-soil reference material. A modified Standard addition method was used to remove the matrix effect.Detection and quantification limits were 0.07 and 0.214 mg/L, respectively.The simple and cost-effective method can be applied to soil samples.

Keywords

Thiosemicarbazides, Fe3+, Fluorescence measurements, complex stoichiometry

References

• Referans1 Crabb E, Moore EA (2009) Metal sand life. RSC Publishing, Cambridge
• Referans2 Waldvogel-Abramowski S, Waeber G, Gassner C, Buser A, Frey MM, Favrat B, Tissota J-D, Physiology of iron metabolism. Transfus Med Hemother, 2014, 41:213–221
• Referans3 Abbaspour N, Hurrell R, Kelishadi R, Review om ıron and its importance for human health . J. R. ın Medical Scıences, 2014, 19: 164-174
• Referans4 Mahmoud ME, Kenawy IMM, Hafez MMAH, Lashein RR, Removal, preconcentration and determination of trace heavy metal ions in water samples by AAS via chemically modified silica gel N- (1-carboxy-6-hydroxy) benzylidenepropylamine ion exchanger, Desalination, 2010, 250:62–70. doi:10.1016/j.desal.2009.09.009
• Referans5 Narin I, Soylak M, Elçi L, Doǧan M, Determination of tracemetal ions by AAS in natural water samples after preconcentrationof pyrocatechol violet complexes on an activated carbon column, Talanta, 2000, 52:1041–1046. doi:10.1016/S0039-9140(00)00468-9
• Referans6 El Ati-Hellal M, Hellal F, Dachraoui M, Hedhili A, Plackett-Burman designs in the pretreatment of macroalgae for Pb, Cr and aldetermination by GF-AAS, Comptes Rendus Chim., 2007, 10:839–849.doi: 10.1016/j.crci.2007.06.
• Referans7 Jamshidi M, Ghaedi M, Mortazavi K et al, Determination of some metal ions by flame-AAS after their preconcentration using sodium dodecyl sulfate coated alumina modified with 2-hydroxy-(3-((1-H-indol 3-yle)phenyl) methyl) 1-H-indol (2-HIYPMI), Food Chem Toxicol, 2011, 49:1229–1234. doi:10.1016/j.fct.2011.02.025
• Referans8 Rykowska I, Wasiak W, Chemically modified silica gel forselective solid-phase extraction and preconcentration of heavy met-al ions, Int J Environ Anal Chem., 2011 91:1466–1476. doi:10.1080/03067319.2010.525745
• Referans9 Wang B-S, Lee C-P, Ho T-Y, Trace metal determination in natural waters by automated solid phase extraction system and ICP-MS: the influence of low level mg and ca, Talanta, 2014 128:337–344. doi:10.1016/j.talanta.2014.04.077
• Referans10 Valeur B, Leray I, Design principles of fluorescent molecularsensors for cation recognition, Coord Chem., 2000, Rev 205:3–40
• Referans11 Gültekin E, Kardil U, Topaloğlu Y, Ocak M, Yıldırım N, Alkan S, Küçük M, Bektaş H, Bekircan O, Synthesis of some new 1,2,4-triazole derivatives, investigation of their fluorescence properties and biological activities, Karadeniz Chem Sci Tech., 2017, 01:36–42
• Referans12 Kamacı M, A fluorescent film probe based on Schiff base for determination of Fe3+ions. Anadolu Univ J Sci Tech A., 2017, Appl Sci Eng 18:613–621
• Referans13 Ji Y, Yu C, Wen S, Zhang J, Characterization of an Al3+-selective fluorescent probe based on a benzoyl hydrazine derivative and its application in cell imaging, Turkısh J of Chem., 2016, 40:625–630
• Referans14 Fındık M, Uçar A, Bingöl H, Güler E, Özcan E, A New synthesis of ferrocene derived Schiff base sensor to determination of Zn2+/Cd2+ ions, 2015 2:47–50 Referans15 B. F. Abdel-Wahab, S. F. Mohamed, A. E.-G. E. Amr, M. M. Abdalla, Monatsh. Chem. 2008, 139, 1083-1090.
• Referans16 S. Singhal, S. Arora, S. Agarwal, R. Sharma, N. Singhal, A review on potential biological activities of thiosemicarbazides, Wor. J. Pharm. Pharm. Sci. 2., 2013, 4661–4681.
• Referans17 A.G. Galina, N.K. Angelina, Thiosemicarbazides in thesynthesis of five- and six membered heterocyclic compounds, Russ. Chem., 2012, Rev. 81:494–523.
• Referans18 A.A. Hassan, A.M. Shawky, Thiosemicarbazides in heterocyclization, J. Hetero.Chem., 2011, 48:495–516.
• Referans19 S.G. Kücükgüzel, E.E. Oruc, S. Rollas, F. Sahin, A. Özbek, Synthesis, characterisation and biologicalactivity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds, Eur. J. Med. Chem., 2002, 37:197–206.
• Referans20 Plech T., Wujec M., Siwek A., Kosikowska U., Malm A., Synthesis and antimicrobial activity of thiosemicarbazides,s-triazoles and their Mannich bases bearing 3-chlorophenyl moiety, European Journal of Medicinal Chemistry., 2011, 46:241-248
• Referans21 Gökçe Cihan-Üstündag, Elif Gürsoy, Lieve Naesens, Nuray Ulusoy-Güzeldemirci, Gültaze Çapa, Synthesis and antiviral properties of novel indole-based thiosemicarbazides and 4-thiazolidinones,Bioorg. Med. Chem., 2016, 24, 240 – 246
• Referans22 Y. Dadaş, G. P. Coşkun, O. Bingol-Akpinar, D. Ozsavci, Ş. G. Kucukguzel,Marmar. Pharm. J. 2015, 19, 259–267.
• Referans23 M. Amir, S. Kumar, ActaPharm. 2007, 57, 31–45.
• Referans24 Eur. J. Med. Chem. 2011, 46, 5283
• Referans25 Siwek, A., Staczek, P., Stefanska, J., Synthesis and structure eactivity relationship studies of 4-arylthiosemicarbazidesas topoisomerase IV inhibitors with Gram-positive antibacterial activity. Searchfor molecular basis of antibacterial activity of thiosemicarbazides,Eur. J.Med.Chem., 2011, 46:5717-5726.
• Referans26 Ali B., Kahan K.M., Kanwal A., Hussain S., Hussain, S., Ashraf M., Raiz M., Waddood A., Perveen S., Synthetic nicotinic/isonicotinic thiosemicarbazides: In vitro urease inhibitory activities and molecular docking studies, Bio org. Chem.,2018, 79, 34–45.
• Referans27 Bharty M.K., Bharti, A., Chaurasia R., Chaudhari U.K., Kushawaha S.K., Sonkar P.K., Ganesan V., Butcher R.J., Synthesis and characterization of Mn(II) complexes of 4-phenyl(phenyl-acetyl)-3-thiosemicarbazide, 4-amino-5-phenyl-1,2,4-triazole-3-thiolate, and their application towards electrochemical oxygen reduction reaction, Polyhedron, 2019 173, 114125.
• Referans28 Qingming W,Yingzi T, Nianhua W, Zhixiang L, Wenling W, A multifunctional fluorescence sensor for Cd2+, PO43− and Cr3+ in different system and the practical application. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, 201, 216-222. doi.org/10.1016/j.saa.2018.05.017
• Referans29 Kumar  A,  Kumar D ,  Chhibbe M, Determination of Mercury Ions in Aqueous Medium and Urine Sample Using Thiocarbohydrazide Based Sensor, Chemistryselect, 2020, 13738-13747. doi.org/10.1002/slct.202002914
• Referans30 Mehraban M,    Manoochehri M,  F. A. Taromi , Trace amount determination of Cd(ii), Pb(ii) and Ni(ii) ions in agricultural and seafood samples after magnetic solid phase extraction by MIL-101(Cr)/phenylthiosemicarbazide-functionalized magnetite nanoparticle composite. New J. Chem., 2018, 176361-7643
• Referans31 Zheng F, Jiantong H, Fengchun J, Mengjiao W, Fengling C, Utilizing the interfacial reaction of naphthalenyl thiosemicarbazide-modified carbon dots for the ultrasensitive determination of Fe (III) ions. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, doi.org/10.1016/j.saa.2019.117485
• Referans32 Bourson J, Valeur B, Ion-responsive fluorescent compounds 2 Cation-steered intra molecular charge transfer in a crowned merocyanine, J. Phys. Chem., 1989, 93, 3871-3876
• Referans33 Ocak M, Ak T, Aktaş A, Özbek N, Çağılcı OC, Gümrükçüoğlu A, Kantekin H, Ocak Ü, Alp H, Metal complexation propertiesof Schiff bases containing 1,3,5-triazine derived from 2-hydroxy-1-naphthaldehyde in solution. A simple spectrofluorimetric method to determine mercury (II), J Fluores, 2017, 27(1):59–68
• Referans34 Özbek N, Alp H, Çelik G, Ak T, Çağılcı OC, Yaylı M, Ocak Ü, Ocak M (2017) A simple spectrofluorimetric sethod for iron determination with a chalcone-based Schiff base, J Fluores, 2017, 27(2):635–641
• Referans35 Başoğlu A, Ocak Ü, Fandaklı S, Yaylı N, A rapid and sensitive spectrofluorometric method for the determination of au(III)based on fluorescence quenching of a 1,3,5-triphenyl-2-pyrazoline, Turk J Chem, 2018, 42:1045–1055
• Referans36 Başoğlu A, Tosun G, Ocak M, Alp H, YaylıN, Ocak Ü, Simple time-saving method for iron determination based on fluorescence quenching of an azaflavanon-3-ol compound, J Agric Food Chem, 2015, 63:2654–2659
• Referans37 Çağlar Y, Saka ET, Alp H, Kantekin H, Ocak Ü, Ocak M, A simple Spectrofluorimetric method based on quenching of a nickel(II)-Phthalocyanine complex to determine iron (III), J Fluoresc, 2016, 26:1381–1389
• Referans38 Bio organic Chemistry, 2019, 79,363–371.