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Schiff Base and Its Fe(II), Zn(II), Ru(II), Pd(II) Complexes Containing ONS Donor Atoms: Synthesis, characterization and Catalytic Studies

Year 2019, Volume: 21 Issue: 61, 73 - 82, 15.01.2019

Abstract

The work include the synthesis,
spectroscopic characterization and as well as catalytic activities of Fe(II),
Zn(II), Ru(II), and Pd(II) complexes with a novel Schiff base ligand derived
from methyl 2-amino-5,5,7,7-tetramethyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate and
salicylaldehyde. Spectroscopic techniques including IR, UV–Vis, NMR, and mass
analysis as well as elemental analysis and magnetic susceptibility measurement
were used to identify the compounds. Based on elemental and spectral studies
octahedral geometry was proposed to Fe(II), Zn(II) and Ru(II) complexes and
square planar geometry was proposed to Pd(II) complex. To improve more
efficient and stable catalysts, we wanted to study if there is any influence
the catalytic activity of ruthenium complex for the transfer hydrogenation of
ketones and we wanted to examine the catalytic activities of palladium complex
in Suzuki C-C cross coupling reactions under various conditions.

References

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  • [19] Kantam, M.L., Annapurna, V., Likhar, P.R., Srinivas, P., Mirzadeh, V., Bhargava, S.K. 2013. Palladium complexes containing multidentate phenoxyepyridyleamidate ligands: Highly efficient catalyst for Heck coupling of deactivated aryl halides, Journal of Organometallic Chemistry, Vol. 723, 129-136 pp. DOI:10.1016/j.jorganchem.2012.08.037
  • [20] Park, S.B., Alper, H, 2003. Highly efficient, recyclable Pd(II) catalysts with bisimidazole ligands for the heck reaction in ionic liquids, Organic Letter, Vol. 5, 3209-3212 pp. DOI: 10.1021/ol030071d
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  • [23] Barbu, L., Popa, M.M., Shova, S., Ferbinteanu, M., Draghici, C.,Dumitrascu, F. 2017.New Pd-NHC PEPPSI complexes from benzimidazolium salts with a phenacyl group attached to N3, Inorganica Chimica Acta, Vol. 463,97-101 pp. DOI: 10.1016/j.ica.2017.04.024
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ONS Donor Atomları İçeren Schiff Bazı ve Fe(II), Zn(II), Ru(II), Pd(II) Kompleksleri: Sentez, Karakterizasyon ve Katalitik Çalışmalar

Year 2019, Volume: 21 Issue: 61, 73 - 82, 15.01.2019

Abstract

Bu
çalışma metil
2-amino-5,5,7,7-tetrametil-4,5,6,7-tetrahidrobenzo[b]tiyofen-3-karboksilat ve
salisilaldehitten elde edilen yeni bir Schiff bazı ligandı ile Fe(II), Zn(II),
Ru(II) ve Pd(II) komplekslerinin sentez, spektroskopik karakterizasyon ilaveten
katalitik aktivitelerini içermektedir. Bileşikleri tanımlamak için element
analiz ve manyetik süsseptibilite ölçümü dâhil olmak üzere IR, UV-Vis, NMR ve
kütle analizi içeren spektroskopik teknikler kullanıldı. Elemental ve spektral
çalışmalara dayanarak, Fe(II), Zn(II) ve Ru(II) komplekslerine oktahedral
geometri ve Pd (II) kompleksine kare düzlem geometri önerildi. Daha etkili ve
kararlı katalizörler geliştirmek için, rutenyum kompleksinin ketonların
hidrojen transferindeki katalitik aktiviteyi etkileyip etkilemediğini ve
paladyum kompleksinin çeşitli koşullar altında
Suzuki C-C çapraz eşleşme tepkimelerindeki katalitik
aktivitelerini
incelemek
istedik.

References

  • [1] Buldurun, K., Turan N., Savcı A., Çolak N. 2018. Synthesis, structural characterization and biological activities of metal(II) complexes with Schiff bases derived from 5-bromosalicylaldehyde: Ru(II) complexes transfer hydrogenation, Journal of Saudi Chemical Society, doi: https://doi.org/10.1016/j.jscs. 2018.06.002 (in press)
  • [2] Manikandan, R., Viswanathamurthi, P., Muthukumar, M. 2011. Ruthenium(II) hydrazone Schiff base complexes: Synthesis, spectral study and catalytic applications, Spectrochim Acta A Mol Biomol Spectrosc., Vol. 83, 297-303 pp. DOI: 10.1016/j.saa.2011.08.033
  • [3] Belal, A.A.M., El-Deen, I.M., Farid, N.Y., Zakaria, R., Refat, M.S. 2015. Synthesis, spectroscopic, coordination and biological activities of some transition metal complexes containing ONO tridentate Schiff base ligand, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 149, 771-787 pp. DOI: 10.1016/j.saa.2015.05.005
  • [4] Orojloo, M., Zolgharnein, P., Solimannejad, M., Amani, S. 2017. Synthesis and characterization of cobalt(II), nickel(II), copper(II) and zinc(II) complexes derived from two Schiff base ligands: Spectroscopic, thermal, magnetic moment, electrochemical and antimicrobial studies, Inorganica Chimica Acta, Vol. 467, 227-237 pp. DOI:10.1016/j.ica.2017.08.016
  • [5] De Araújo, E.L., Barbosa, H.F.G., Dockal, E.R., Cavalheiro, T.G. 2017. Synthesis, characterization and biological activity of Cu(II), Ni(II) and Zn(II) complexes of biopolymeric Schiff bases of salicylaldehydes and chitosan, International Journal of Biological Macromolecules, Vol. 95, 168-176 pp.DOI:10.1016/j.ijbiomac.2016.10.109
  • [6] Modha, S.G., Mehta, V.P., Van der Eycken, E.V. 2013. Transition metal-catalyzed C–C bond formation via C–S bond cleavage: an overview, Chemical. Society. Reviews, Vol. 42, 5042-5055 pp. DOI: 10.1039/c3cs60041f.
  • [7] Pal, S., Hwang, W.S., Lin, I.J.B., Lee, C.S. 2007.Benzene benzimidazole containing Pd(II) metallacycle: Synthesis, X-ray crystallographic characterization and its use as an efficient Suzuki coupling catalyst, Journal of Molecular Catalysis A: Chemical, Vol. 269, 197-203 pp. DOI:10.1016/j.molcata.2007.01.028
  • [8] Bian, H.D., Wang, J., Wei, Y., Tang, J., Huang, F.P., Yao, D., Yu, Q., Liang, H. 2015. Superoxide dismutase activity studies of Mn(III)/Cu(II)/Ni(II) complexes with Schiff base ligands, Polyhedron, Vol. 90, 147-153 pp. DOI:10.1016/j.poly.2015.01.022
  • [9] Abou-Hussein, A.A., Linert, W. 2015. Synthesis, spectroscopic studies and inhibitory activity against bactria and fungi of acyclic and macrocyclic transition metal complexes containing a triamine coumarine Schiff base ligand, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 141, 223-232 pp. DOI:10.1016/j.saa.2015.01.063
  • [10] Roy, N., Sproules, S., Bothe, E., Weyhermüller, T., Wieghardt, K. 2009. Polynuclear Complexes containing the redox noninnocent Schiff base ligand 2-[(E)-2-mercaptophenylimino]methyl-4,6-di-tert-butylphenolate(2–), European Journal of Inorganic Chemistry, Vol. 2009, 2655-2663 pp. DOI: 10.1002/ejic.200900168
  • [11] Gupta, K.C., Sutar, A.K, 2008. Catalytic activity of Schiff base complexes, Coordination Chemistry Reviews, Vol. 252, 1420-50 pp.DOI:10.1016/j.ccr.2007.09.005
  • [12] Islam, S.M., Mondal, P., Roy, A.S., Mondal, S., Hossain, D. 2010. Heterogeneous Suzuki and copper-free Sonogashira cross-coupling reactions catalyzed by a reusable palladium(II) complex in water medium, Tetrahedron Letter, Vol. 51, 2067-2070 pp. DOI:10.1016/j.tetlet.2010.02.079
  • [13] Diederich, F., Stang, P.J. 1998. Metal catalyzed cross–coupling reactions, Wiley–VCH, Weinheim. Vol. 878, 12 pp. DOI: 10.1002/(SICI)1099-0739(199812)
  • [14] Bakherad, M., Keivanloo, A., Amin, A.H., Jajarmi S. 2012. Phosphine-free polystyrene-supported palladium(II) complex as anefficient catalyst for the Heck and Suzuki coupling reactions in water, Comptes Rendus Chimie, Vol. 15, 945-949 pp. DOI:10.1016/j.crci.2012.06.009
  • [15] Rao, G.K., Kumar, A., Bhunia, M., Singh, M.P., Singh, A.K. 2014. Complex of 2-(methylthio)aniline with palladium(II) as an efficient catalyst for Suzuki–Miyaura C-C coupling in eco-friendly water, Journal of Hazardous Materials, Vol. 269, 18-23 pp. DOI: 10.1016/j.jhazmat.2013.11.045
  • [16] Navidi, M., Rezaei, N., Movassagh, B. 2013.Palladium(II)–Schiff base complex supported on multi-walled carbon nanotubes: A heterogeneous and reusable catalyst in the Suzuki–Miyaura and copper-free Sonogashira–Hagihara reactions, Journal of Organometallic Chemistry, Vol. 743, 63-69 pp. DOI:10.1016/j.jorganchem.2013.06.021
  • [17] Albayrak Kas, Ç., Kas, G., Güder, A., Gür, M., Muğlu, H., Büyükgüngör, O. 2017. Investigation of two o-hydroxy Schiff bases in terms of prototropy and radical scavenging activity, Journal of Molecular Structure, Vol. 1130, 623-632 pp. DOI:10.1016/j.molstruc.2016.11.023
  • [18] Mieczyn´ska, E., Lisowski, J., Trzeciak, A.M. 2015. A macrocyclic Pd(II)–Ni(II) complex in Heck and Suzuki reactions, Inorganica Chimica Acta, Vol. 431, 145-149 pp. DOI:10.1016/j.ica.2014.11.008
  • [19] Kantam, M.L., Annapurna, V., Likhar, P.R., Srinivas, P., Mirzadeh, V., Bhargava, S.K. 2013. Palladium complexes containing multidentate phenoxyepyridyleamidate ligands: Highly efficient catalyst for Heck coupling of deactivated aryl halides, Journal of Organometallic Chemistry, Vol. 723, 129-136 pp. DOI:10.1016/j.jorganchem.2012.08.037
  • [20] Park, S.B., Alper, H, 2003. Highly efficient, recyclable Pd(II) catalysts with bisimidazole ligands for the heck reaction in ionic liquids, Organic Letter, Vol. 5, 3209-3212 pp. DOI: 10.1021/ol030071d
  • [21] Anan, N.A., Hassan, S.M., Saad, E.M., Butler, I.S., Mostafa, S.I. 2011. Preparation, characterization and pH-metric measurements of 4-hydroxysalicylidenechitosan Schiff-base complexes of Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Ru(III), Rh(III), Pd(II) and Au(III), Carbohydrate Research, Vol. 346,775-793 pp. DOI:10.1016/j.carres.2011.01.014
  • [22] Kundu, S., Pramanik, A.K., Mondal, A.S., Mondal, T.K. 2016. Ni(II) and Pd(II) complexes with new N,O donor thiophene appended Schiff base ligand: Synthesis, electrochemistry, X-ray structure and DFT calculation, Journal of Molecular Structure, Vol. 1116,1-8 pp. DOI:10.1016/j.molstruc.2016.03.013
  • [23] Barbu, L., Popa, M.M., Shova, S., Ferbinteanu, M., Draghici, C.,Dumitrascu, F. 2017.New Pd-NHC PEPPSI complexes from benzimidazolium salts with a phenacyl group attached to N3, Inorganica Chimica Acta, Vol. 463,97-101 pp. DOI: 10.1016/j.ica.2017.04.024
  • [24] Agrahari, B., Layek, S., Ganguly Anuradha, R., Pathak, D.D. 2018. Synthesis crystal structures and application of two new pincer type palladium(II)-Schiff base complexes in C-C cross-coupling reactions, Inorganica Chimica Acta, Vol. 471, 345-354 pp. DOI:10.1016/j.ica.2017.11.018
  • [25] Wang, L., Yang, Q., Chen, H., Li, R.X, 2011. A novel cationic dinuclear ruthenium complex: Synthesis,characterization and catalytic activity in the transfer hydrogenation of ketones, Inorganic Chemistry Communications, Vol. 14, 1884-1888 pp. DOI:10.1016/j.inoche.2011.09.003
  • [26] Sece, J.M., Quiros, M., Garmendina, M.J.G, 2000. Synthesis, X-ray crystal structure and spectroscopic, magnetic and EPR studies of copper(II) dimers with methoxy-di-(2-pyridyl)methoxide as bridging ligand, Polyhedron, Vol. 19, 1005-1013 pp. PII S0277-5387(0 0)00356-9
  • [27] Dehkhodaei, M., Khorshidifard, M., Rudbari, H.A., Sahihi, M., Azimi, G., Habibi, N., Taheri, S., Bruno, G., Azadbakht, R. 2017. Synthesis, characterization, crystal structure and DNA, HSA-binding studies of four Schiff base complexes derived from salicylaldehyde and isopropylamine, Inorganica Chimica Acta, Vol. 466, 48-60 pp. DOI: 10.1016/j.ica.2017.05.035
  • [28] Tamizh, M.M., Cooper, B.F.T., Macdonald, C.L.B., Karvembu, R. 2013. Palladium(II) complexes with salicylideneimine based tridentate ligand and triphenylphosphine: Synthesis, structure and catalytic activity in Suzuki–Miyaura cross coupling reactions, Inorganica Chimica Acta, Vol. 394, 391-400 pp. DOI: 10.1016/j.ica.2012.08.024
  • [29] Nithya, P., Simpson, J., Govindarajan, S. 2017. Template synthesis, structural variation, thermal behavior and antimicrobial screening of Mn(II), Co(II) and Ni(II) complexes of Schiff base ligands derived from benzyl carbazate and three isomers of acetylpyridine, Inorganica Chimica Acta, Vol. 467, 180-193 pp. DOI:10.1016/j.ica.2017.07.059
  • [30] Anupama, B., Sunita, M., Shiva Leela, D., Ushaiah, B., Gyana Kumari, C. 2014. Synthesis, spectral characterization, DNA binding studies and antimicrobial activity of Co(II), Ni(II), Zn(II), Fe(III) and VO(IV) complexes with 4-aminoantipyrine Schiff base of ortho-vanillin,Journal of Fluorescence, Vol. 24, 1067-1076 pp. DOI: 10.1007/s10895-014-1386-z
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There are 37 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Kenan Buldurun 0000-0002-2462-7006

Naki Çolak 0000-0001-7181-9556

İsmail Özdemir 0000-0001-6325-0216

Nevin Turan 0000-0001-6740-6812

Publication Date January 15, 2019
Published in Issue Year 2019 Volume: 21 Issue: 61

Cite

APA Buldurun, K., Çolak, N., Özdemir, İ., Turan, N. (2019). Schiff Base and Its Fe(II), Zn(II), Ru(II), Pd(II) Complexes Containing ONS Donor Atoms: Synthesis, characterization and Catalytic Studies. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen Ve Mühendislik Dergisi, 21(61), 73-82.
AMA Buldurun K, Çolak N, Özdemir İ, Turan N. Schiff Base and Its Fe(II), Zn(II), Ru(II), Pd(II) Complexes Containing ONS Donor Atoms: Synthesis, characterization and Catalytic Studies. DEUFMD. January 2019;21(61):73-82.
Chicago Buldurun, Kenan, Naki Çolak, İsmail Özdemir, and Nevin Turan. “Schiff Base and Its Fe(II), Zn(II), Ru(II), Pd(II) Complexes Containing ONS Donor Atoms: Synthesis, Characterization and Catalytic Studies”. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen Ve Mühendislik Dergisi 21, no. 61 (January 2019): 73-82.
EndNote Buldurun K, Çolak N, Özdemir İ, Turan N (January 1, 2019) Schiff Base and Its Fe(II), Zn(II), Ru(II), Pd(II) Complexes Containing ONS Donor Atoms: Synthesis, characterization and Catalytic Studies. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi 21 61 73–82.
IEEE K. Buldurun, N. Çolak, İ. Özdemir, and N. Turan, “Schiff Base and Its Fe(II), Zn(II), Ru(II), Pd(II) Complexes Containing ONS Donor Atoms: Synthesis, characterization and Catalytic Studies”, DEUFMD, vol. 21, no. 61, pp. 73–82, 2019.
ISNAD Buldurun, Kenan et al. “Schiff Base and Its Fe(II), Zn(II), Ru(II), Pd(II) Complexes Containing ONS Donor Atoms: Synthesis, Characterization and Catalytic Studies”. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi 21/61 (January 2019), 73-82.
JAMA Buldurun K, Çolak N, Özdemir İ, Turan N. Schiff Base and Its Fe(II), Zn(II), Ru(II), Pd(II) Complexes Containing ONS Donor Atoms: Synthesis, characterization and Catalytic Studies. DEUFMD. 2019;21:73–82.
MLA Buldurun, Kenan et al. “Schiff Base and Its Fe(II), Zn(II), Ru(II), Pd(II) Complexes Containing ONS Donor Atoms: Synthesis, Characterization and Catalytic Studies”. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen Ve Mühendislik Dergisi, vol. 21, no. 61, 2019, pp. 73-82.
Vancouver Buldurun K, Çolak N, Özdemir İ, Turan N. Schiff Base and Its Fe(II), Zn(II), Ru(II), Pd(II) Complexes Containing ONS Donor Atoms: Synthesis, characterization and Catalytic Studies. DEUFMD. 2019;21(61):73-82.

Dokuz Eylül Üniversitesi, Mühendislik Fakültesi Dekanlığı Tınaztepe Yerleşkesi, Adatepe Mah. Doğuş Cad. No: 207-I / 35390 Buca-İZMİR.