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Synthesis, characterization and crystal structure of platinum(II) complexes with thiourea derivative ligands


Ebru Keskin (1) orcid , Ummuhan Solmaz (2) orcid , Gun Binzet (3) orcid , Ilkay Gumus (4,*) orcid , Hakan Arslan (5) orcid

(1) Advanced Technology Research and Application Center, Mersin University, Mersin, TR-33343, Turkey
(2) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR-33343, Turkey
(3) Department of Chemistry, Faculty of Education, Mersin University, Mersin, TR-33343, Turkey
(4) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR-33343, Turkey
(5) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR-33343, Turkey
(*) Corresponding Author

Received: 16 Jul 2018 | Revised: 12 Oct 2018 | Accepted: 15 Oct 2018 | Published: 31 Dec 2018 | Issue Date: December 2018

Abstract


Thiourea derivatives [N-(di-n-propylcarbamothioyl)-4-fluorobenzamide (HL1) and N-(di-n-propylcarbamothioyl)-4-bromobenzamide (HL2)] and their platinum complexes have been successfully synthesized and structurally characterized by spectroscopic 1H NMR, 13C NMR, COSY, HMQC, and FT-IR techniques. The structure of both complexes was also confirmed by single crystal X-ray diffraction studies. The study of X-ray single crystal diffraction shows that the supramolecular aggregation of the complexes is stabilized via weak interactions as well as stacking interactions such as C-H⋅⋅⋅π and π⋅⋅⋅π. The cis-[Pt(L1-S,O)2 showed C–H⋯π and π⋯π stacking interactions, whereas only C–H⋯π stacking interaction was observed in cis-[Pt(L2-S,O)2]. In addition, the strong classical and non-classical intermolecular hydrogen bonds are not found in the prepared complexes. Therefore, it can be said that the C–H⋯π and π⋯π stacking interactions play an important role in the formation of supramolecular structures of the complexes.


Keywords


Thiourea; Synthesis; Platinum complexes; Benzamide derivative; Supramolecular structure; Single crystal X‐ray diffraction

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DOI: 10.5155/eurjchem.9.4.360-368.1774

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Funding information


This work was supported by the Mersin University Research Fund [Project No: 2016-AP4-1426].

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References


[1]. Khawar, R. M.; Imtiaz-ud-Din, A.; Badshah, M.; Ebihara G. M.; de Vos, D.; Ahmed, S. J. Inorg. Biochem. 2009, 103, 1135-1144.

[2]. Saswati, A.; Dash, S. P.; Panda A. K.; Acharyya, R.; Biswas, A.; Mukhopadhyay, S.; Bhutia, S. K.; Crochet, A.; Patil, Y. P.; Nethaji; M.; Dinda, R. Dalton Trans. 2015, 44, 6140-6157.
https://doi.org/10.1039/C4DT03764B

[3]. Lobana,T. S.; Kumari, P.; Sharma, R.; Castineiras, A.; Butcher, R. J.; Akitsu, T.; Aritake, Y. Dalton Trans. 2011, 40, 3219-3228.
https://doi.org/10.1039/c0dt01291b

[4]. Bowmaker, G. A.; Chaichit, N.; Hanna, J. V.; Pakawatchai, C.; Skelton, B. W.; White, A. H. Dalton Trans. 2009, 39, 8308-8310.
https://doi.org/10.1039/b909167j

[5]. Gumus, I.; Gonca, S.; Arslan, B.; Keskin, E.; Solmaz, U.; Arslan, H. Eur. J. Chem. 2017, 8(4), 410‐416.
https://doi.org/10.5155/eurjchem.8.4.410-416.1650

[6]. Blower, P. J.; Castle, T. C.; Cowley, A. R.; Dilworth, J. R.; Donnelly, P. S.; Labisbal, E.; Sowrey, F. E.; Teat, S. J.; Went, M. J. Dalton Trans. 2003, 23, 4416-4425.
https://doi.org/10.1039/B307499D

[7]. Hollmann, K.; Oppermann, A.; Witte, M.; Li, S.; Amen, M.; Florke, U.; Egold, H.; Henkel, G.; Herres-Pawlis, S. Eur. J. Inorg. Chem. 2017, 9, 1266-1279.
https://doi.org/10.1002/ejic.201601547

[8]. Lobana, T. S.; Khanna, S.; Butcher, R. J. Dalton Trans. 2012, 4, 14845-14851.

[9]. Baldini, M.; Belicchi-Ferrari, M.; Bisceglie, F.; Dall'Aglio, P. P.; Pelosi, G.; Pinelli, S.; Tarasconi, P. Inorg. Chem. 2004, 43, 7170-7179.
https://doi.org/10.1021/ic049883b

[10]. Singh, D. P.; Pratap, S.; Shukla, M. Inorg. Chim. Acta 2014, 423,386-396.
https://doi.org/10.1016/j.ica.2014.08.031

[11]. Bacher, F.; Domotor, O.; Chugunova, A., Nagy, N. V.; Filipovic, L.; Radulovic, S.; Enyedy, E. A.; Arion, V. B. Dalton Trans. 2015, 44, 9071-9090.
https://doi.org/10.1039/C5DT01076D

[12]. Cowley, A. R.; Dilworth, J. R.; Donnelly, P. S.; Gee, A. D.; Heslop, J. M. Dalton Trans. 2004, 16, 2404-2412.
https://doi.org/10.1039/b406429a

[13]. Gomez-Saiz, P.; Gil-Garcia, R.; Maestro, M. A.; Pizarro, J. L.; Arriortua, M. I.; Lezama, L.; Rojo, T.; Gonzalez-Alvarez, M.; Borras, J.; Garcia-Tojal, J. J. Inorg. Biochem. 2008, 102, 1910-1920.
https://doi.org/10.1016/j.jinorgbio.2008.06.015

[14]. Lopez-Torres, E.; Cowley, A. R; Dilworth, J. R. Dalton Trans. 2007, 1194-1196.
https://doi.org/10.1039/B617186A

[15]. Drzewiecka-Antonik, A.; Rejmak, P.; Klepka, M. T.; Wolska, A.; Pietrzyk, P.; Stepien, K.; Sanna, G.; Struga, M. J. Inorg. Biochem. 2017, 176, 8-16.
https://doi.org/10.1016/j.jinorgbio.2017.08.001

[16]. Saeed, A.; Bolte, M.; Erben, M. F.; Perez, H. CrystEngComm 2015, 17, 7551-7563.
https://doi.org/10.1039/C5CE01373A

[17]. Estevez-Hernandez, O.; Sanchez, E. O.; Hidalgo-Hidalgo de Cisneros, J. L.; Naranjo-Rodriguez, L.; Reguera, E. Spectrochim. Acta A 2006, 64, 961-971.
https://doi.org/10.1016/j.saa.2005.09.005

[18]. Dago, A.; Shepelev, Y.; Fajardo, F.; Alvarez, F.; Pomes, R. Acta Cryst. C 1989, 45, 1192-1194.
https://doi.org/10.1107/S0108270189000119

[19]. Koch, K. R.; Sacht, C.; Bourne, S. Inorg. Chim. Acta 1995, 232, 109-113.
https://doi.org/10.1016/0020-1693(94)04375-6

[20]. Estevez-Hernandez, O.; Sanchez,E. O.; Hidalgo-Hidalgo de Cisneros, J. L; Naranjo- Rodrıguez, L.; Reguera, E. Spectrochim. Acta A 2005, 62, 964-971.

[21]. Elhusseiny, A. F.; Eldissouky, A.; Al-Hamza, A. M.; Hassan, H. H. A. M. J. Mol. Struct. 2015, 1100, 530-545.
https://doi.org/10.1016/j.molstruc.2015.07.049

[22]. Kaminsky, W.; Kelman, D. R.; Giesen, J. M.; Goldberg, K. I.; Claborn, K. A.; Szczepura, L. F.; West, D. X. J. Mol. Struct. 2002, 616, 79-89.
https://doi.org/10.1016/S0022-2860(02)00300-9

[23]. Wu, F. Y.; Li, Z.; Guo, L.; Wang, X.; Lin, M. H.; Zhao, Y. F.; Jiang, Y. B. Org. Biomol. Chem. 2006, 4, 624-630.
https://doi.org/10.1039/b513969d

[24]. Saeed, A.; Erben, M. F.; Abbas, N.; Florke, U. J. Mol. Struct. 2010, 984, 240-245.
https://doi.org/10.1016/j.molstruc.2010.09.035

[25]. Karipcin, F.; Atis, M.; Sariboga, B.; Celik, H.; Tas, M. J. Mol. Struct. 2013, 1048, 69-77.
https://doi.org/10.1016/j.molstruc.2013.05.042

[26]. Koch, K. R. Coord. Chem. Rev. 2001, 216-217, 473-488.
https://doi.org/10.1016/S0010-8545(01)00337-X

[27]. Saeed, A.; Khurshid, A.; Bolte, M.; Fantoni, A. C.; Erben, M. F. Spectrochim. Acta A 2015, 143, 59-66.
https://doi.org/10.1016/j.saa.2015.02.042

[28]. Bailey, R. A.; Rothaupt, K. L. Inorg. Chim. Acta 1988, 147, 233-236.
https://doi.org/10.1016/S0020-1693(00)83377-0

[29]. Westra, A. N.; Bourne, S. A.; Esterhuysen, C.; Koch, K. R. Dalton Trans. 2005, 12, 2162-2172.
https://doi.org/10.1039/b503653d

[30]. Molter, A.; Mohr, F. Coord. Chem. Rev. 2010, 254, 19-45.
https://doi.org/10.1016/j.ccr.2009.09.017

[31]. Sacht, C.; Datt, M. S.; Otto, S.; Roodt, A. J. Chem. Soc. Dalton Trans. 2000, 47, 4579-4586.
https://doi.org/10.1039/b007589m

[32]. Gu, C. L.; Liu, L.; Zhao, J. L.; Wang, D. Y. Tetrahedron 2007, 18, 455-463.
https://doi.org/10.1016/j.tetasy.2007.02.016

[33]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Cryst. 2009, 42, 339-341.
https://doi.org/10.1107/S0021889808042726

[34]. Palatinus, L.; Chapuis, G. J. Appl. Cryst. 2007, 40, 786-790.
https://doi.org/10.1107/S0021889807029238

[35]. Palatinus, L.; van der Lee, A. J. Appl. Cryst. 2008, 41, 975-984.
https://doi.org/10.1107/S0021889808028185

[36]. Palatinus, L.; Prathapa, S. J.; van Smaalen S. J. Appl. Cryst. 2012, 45, 575-580.
https://doi.org/10.1107/S0021889812016068

[37]. Sheldrick, G. M. Acta Crystallogr. C 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218

[38]. Arslan, H.; Florke, U.; Kulcu, N.; Kayhan, E. Turk. J. Chem. 2006, 30, 429-440.

[39]. Binzet, G.; Arslan, H.; Florke, U.; Kulcu, N.; Duran, N. J. Coord. Chem. 2006, 59,1395-1406.
https://doi.org/10.1080/00958970500512633

[40]. Gumus, I.; Solmaz, U.; Celik, O.; Binzet, G.; Balcı, G. K.; Arslan, H. Eur. J. Chem. 2015, 6(3), 237-241.
https://doi.org/10.5155/eurjchem.6.3.237-241.1265

[41]. Arslan, H.; Vanderveer, D.; Emen, F.; Kulcu. N.; Z. Krist-New Cryst. St. 2003, 218, 479-480.

[42]. Avsar, G.; Arslan, H.; Haupt, H. J.; Kulcu. N. Turk. J. Chem. 2003, 27, 281-286.

[43]. Binzet, G.; Florke, U.; Kulcu, N.; Arslan, H. Eur. J. Chem. 2012, 3(1), 37‐39.
https://doi.org/10.5155/eurjchem.3.1.37-39.591

[44]. Binzet, G.; Florke, U.; Kulcu, N.; Arslan, H. Eur. J. Chem. 2012, 3(2), 211‐213.
https://doi.org/10.5155/eurjchem.3.2.211-213.594

[45]. Ozpozan, N.; Ozpozan, T.; Arslan, H.; Kulcu, N. Thermochim. Acta 1999, 336, 97-103.
https://doi.org/10.1016/S0040-6031(99)00208-7

[46]. Ozpozan, N.; Arslan, H.; Ozpozan, T.; Merdivan, M.; Kulcu, N. J. Therm. Anal. Calorim. 2000, 61, 955-965.
https://doi.org/10.1023/A:1010171230450

[47]. Arslan, H.; Algul, O. Inter. J. Mol. Sci. 2007, 8, 770-776.

[48]. Arslan, H.; Vanderveer, D.; Emen, F.; Kulcu, N. Z. Krist-New Cryst. St. 2003, 218, 479-480.

[49]. Ozer, C. K.; Arslan, H.; VanDerveer, D.; Kulcu, N. Molecules 2009, 14, 655-666.
https://doi.org/10.3390/molecules14020655

[50]. Ozer, C. K.; Arslan, H.; VanDerveer, D.; Binzet, G. J. Coord. Chem. 2009, 62, 266-276.
https://doi.org/10.1080/00958970802209623

[51]. Joseph, M.; Suni, V.; Nayar, C. R.; Kurup, M. R. P.; Fun, H. K. J. Mol. Struct. 2004, 705, 63-70.
https://doi.org/10.1016/j.molstruc.2004.06.018

[52]. Kohn, U.; Gunther, W.; Gorls, H.; Anders, E. Tetrahedron: Asym. 2004, 15, 1419-1426.
https://doi.org/10.1016/j.tetasy.2004.03.016

[53]. Selvakumaran, N.; Pratheepkumar, A.; Ng, S. W.; Tiekink, E. R. T.; Karvembu, R. Inorg. Chim. Acta 2013, 404, 82-87.
https://doi.org/10.1016/j.ica.2013.04.024

[54]. Reilly, B. O.; Plutin, A. M.; Perez, H.; Calderon, O.; Ramos, R.; Martinez, R.; Toscano, R. A.; Duque, J.; Rodriguez-Solla, H.; Martinez-Alvarez, R.; Suarez, M.; Martin, N. Polyhedron 2012, 36, 133-140.
https://doi.org/10.1016/j.poly.2012.02.008

[55]. Solmaz, U.; Gumus, I.; Binzet, G.; Celik, O.; Balci, G. K.; Dogen, A.; Arslan, H. J. Coord. Chem. 2018, 71, 200-218.
https://doi.org/10.1080/00958972.2018.1427233

[56]. Jiang, Y.; Xi, C.; Liu, Y.; Niclos‐Gutierrez, J.; Choquesillo‐Lazarte, D. Eur. J. Inorg. Chem. 2005, 8, 1585-1588.
https://doi.org/10.1002/ejic.200400864

[57]. Roy, S.; Drew, M. G. B.; Bauza, A.; Frontera, A.; Chattopadhyay, S. Dalton Trans. 2017, 46, 5384-5397.
https://doi.org/10.1039/C6DT04906K

[58]. Gumus, I.; Solmaz, U.; Binzet, G.; Keskin, E.; Arslan, B.; Arslan, H. J. Mol. Struct. 2018, 1157, 78-88.
https://doi.org/10.1016/j.molstruc.2017.12.017

[59]. Gumus, I.; Solmaz, U.; Gonca, S.; Arslan, H. Eur. J. Chem. 2017, 8(4), 349‐357.
https://doi.org/10.5155/eurjchem.8.4.349-357.1637


Supporting information


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How to cite


Keskin, E.; Solmaz, U.; Binzet, G.; Gumus, I.; Arslan, H. Eur. J. Chem. 2018, 9(4), 360-368. doi:10.5155/eurjchem.9.4.360-368.1774
Keskin, E.; Solmaz, U.; Binzet, G.; Gumus, I.; Arslan, H. Synthesis, characterization and crystal structure of platinum(II) complexes with thiourea derivative ligands. Eur. J. Chem. 2018, 9(4), 360-368. doi:10.5155/eurjchem.9.4.360-368.1774
Keskin, E., Solmaz, U., Binzet, G., Gumus, I., & Arslan, H. (2018). Synthesis, characterization and crystal structure of platinum(II) complexes with thiourea derivative ligands. European Journal of Chemistry, 9(4), 360-368. doi:10.5155/eurjchem.9.4.360-368.1774
Keskin, Ebru, Ummuhan Solmaz, Gun Binzet, Ilkay Gumus, & Hakan Arslan. "Synthesis, characterization and crystal structure of platinum(II) complexes with thiourea derivative ligands." European Journal of Chemistry [Online], 9.4 (2018): 360-368. Web. 22 Mar. 2023
Keskin, Ebru, Solmaz, Ummuhan, Binzet, Gun, Gumus, Ilkay, AND Arslan, Hakan. "Synthesis, characterization and crystal structure of platinum(II) complexes with thiourea derivative ligands" European Journal of Chemistry [Online], Volume 9 Number 4 (31 December 2018)

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