Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Synthesis and Characterization of Unsymmetrical Schiff Base Complexes Containing Thioether Donor with Mn(II), Co(III), Ni(II), Cu(II) and Cd(II) Metals Ions

Document Type : Research Article

Authors
Ahmad Ali Dehghani-Firouzabadi 1
Syedeh Maryam Hosseinimoghadam 2
1 Department of Chemistry, Yazd University, Yazd, I.R. IRAN
2 Depaement of Chemistry, Yazd University, Yazd, Iran
Abstract
For the preparation of the ligand, 2-((2-(2-(pyridine-2-ylmethyleneamino) phenylthio)ethylimino)methyl)phenol (HL), at first, unymmetric thioethere amine 2-(2-aminoethylthio)-N-(pyridine-2-ylmethyleneanilin) has been prepared through nucleophilic substitution of 2-aminothiophenol with N-(2-bromoethyl)phthalimide, then condensed with pyridine-2-carbaldehyde and then phthalimide group removed with hydrazine hydrate. Then Schiff base ligand HL was prepared via condensation of this unsymmetrical thioether amine with 2-hydroxybenzaldehyde. Mn(II), Co(III), Ni(II), Cu(II) and Cd(II) Schiff base complexes of this ligand have been synthesized. The thioether amine and unsymmetrical Schiff base ligand were characterized by appropriate spectroscopic methods such as IR, 1H NMR, 13C NMR studies, and also unsymmetrical Schiff base complexes were characterized by IR, UV-Vis,  molar conductivity and elemental analysis methods.
Keywords
Thioether ligand
Unsymmetrical Schiff base ligand
Unsymmetrical Schiff base complex
Unsymmetrical amine

Subjects

[1] Reger T. S., Janda K. D., Polymer-Supported (Salen)Mn Catalysts for Asymmetric Epoxidation:  A Comparisonbetween Soluble and Insoluble Matrices, J. Am. Chem. Soc. 122(29): 6929-6934 (2000).
[2] Nakajima K., Ando Y., Mano H., Kojima M., Photosubstitution reactivity, crystal structures, and electrochemistry of ruthenium (II)(III) complexes containing tetradentate (O2N2, S2N2, and P2N2) Schiff base ligands, Inorg. Chim. Acta 274(2):  184-191 (1998).
[3] Brewer G., Kamaras P., May L., Prytkov S., Rapta M., Synthesis and structural characterization of metal complexes of an unsymmetric N3O tetradentate Schiff base ligand, Inorg. Chim. Acta 279(1): 111-115 (1998).
[4] Yam V. W., Lo K. K., Luminescent polynuclear d10 metal complexes, Chem. Soc. Rev. 28: 323-334 (1999).
[5] McMillin D. R., McNett K. M., Photoprocesses of copper complexes that bind to DNA, Chem. Rev. 98(3): 1201-1220 (1998).
[6] Akbar Ali M., Mirza A. H., Ting W. Y., Haniti M., Hamid S. A., Bernhardt P. V., Butcher R. J., Mixed-ligand nickel(II) and copper(II) complexes of tridentate ONS and NNS ligands derived from S-alkyldithiocarbazates with the saccharinate ion as a co-ligand, Polyhedron 48(1): 167-173 (2012).
[7] Manikandan R., Viswnathamurthi P., Coordination behavior of ligand based on NNS and NNO donors with ruthenium(III) complexes and their catalytic and DNA interaction studies, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 97: 864-870 (2012).
[8] Shafaatian B., Soleymanpour A., Oskouei N. K., Notash B., Rezvani S. A., Synthesis, crystal structure, fluorescence and electrochemical studies of a new tridentate Schiff base ligand and its nickel(II) and palladium(II) complexes, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 128: 363-369 (2014).
[9] Hosseini-Monfared H., Kheirabadi S., Asghari-Lalami N., Mayer P., Dioxo- and oxovanadium(V) complexes of biomimetic hydrazone ONO and NNS donor ligands: Synthesis, crystal structure and catalytic reactivity, Polyhedron 30(8): 1375-1384 (2011).
[10] Chang S., Karambelkar V. V., Sommer R. D., Rheingold A. L., Goldberg D. P., New Monomeric Cobalt(II) and Zinc(II) Complexes of a Mixed N,S(alkylthiolate) Ligand:  Model Complexes of (His)(His)(Cys) Metalloprotein Active Sites, Inorg. Chem.41(2): 239-248 (2002).
[11] Karahan A., Karabulut S., Dal H., Kurtaran R., Leszczynski J., Experimental and theoretical investigation of a novel mononuclear copper(II) azido compound with tridentate (NNO) Schiff base, J. Mol. Struct.1093: 1-7 (2015).
[12] Singh R., Banerjee A., Rajak K. K., Iron(III) complexes using NNS reduced Schiff bases and NNOS coordinating tetradentate ligands: Synthesis, structure and catecholase activity, Inorg. Chim. Acta 363(12): 3131-3138(2010).
[13] Jana S., Jana M. S., Biswas S., Sinha C., Mondal T. K., Synthesis, electronic structure and catalytic activity of ruthenium-iodo-carbonyl complexes with thioether containing NNS donor ligand, J. Mol. Struct.1065-1066: 52-60 (2014).
[14] Kim S., Ginsbach J. W., Billah A. I., Siegler M. A., Moore C. D., Solomon E. I., Karlin K. D., Tuning of the Copper–Thioether Bond in Tetradentate N3S(thioether) Ligands; O–O Bond Reductive Cleavage via a [CuII2(μ-1,2-peroxo)]2+/[CuIII2(μ-oxo)2]2+ Equilibrium, J. Am. Chem. Soc. 136(22): 8063-8071 (2014).
[15] Kalita M., Bhattacharjee T., Gogoi P., Barman P., Kalita R. D., Synthesis, characterization, crystal structure and bioactivities of a new potential tridentate (ONS) Schiff base ligand N-[2-(benzylthio) phenyl] salicylaldimine and its Ni(II), Cu(II) and Co(II) complexes, Polyhedron 60: 47-53 (2013).
[16] یگانه فعال، علی؛ موجدیان، مریم؛ کلهر، مهدی؛ عطاران، عبدالمحمد؛  تبارکی، رضا؛ تهیه مشتق تازه­ای از بازشیف تیوفن تتراهیدروبنزو و کاربرد آن در اندازه­گیری فلوئورید در خمیردندان به عنوان یک حسگر تازه فلورسانی فلوئورید، نشریهشیمیومهندسیشیمیایران، (3) 35: 65 تا 75 (1395).
[17] Brand U., Burth R., Vahrenkamp H., Design of Trigonal-Bipyramidal ZnN3S2 Complexes, Inorg. Chem.35(4): 1083-1086 (1996).
[18] Zhang Z., Martell A. E., Motekaitis R. J., Fu L., Synthesis of pentadentate mixed NS dithiolate chelating ligands derived from heterocycles and 2-mercaptoethylamines, Tetrahedron lett.40(25): 4615-4618(1999).
[19] Chandra S., Gupta K., Chromium(III), manganese(II), iron(III), cobalt(II), nickel(II) and copper(II) complexes with a pentadentate, 15-membered new macrocyclic ligand, Trans. Met. Chem.27(2): 196-199 (2002).
[20] Ganjali M. R., Pourjavid M. R., Rezapour M., Haghgoo S., Novel samarium(III) selective membrane sensor based on glipizid, Sens. Actuators B: Chemical 89(1-2): 21-26 (2003).
[21] Ganjali M. R., Rahimi M., Maddah B., Moghimi A., Borhani S., An Eu(III) Sensor Based on N,N-Diethyl-N-(4-hydroxy-6-methylpyridin-2-yl)guanidine, Anal. Sci.20(10): 1427-1431 (2004).
[22] Shamsipur M., Yousefi M., Hosseini M., Ganjali M. R., Lanthanum(III) PVC Membrane Electrodes Based on 1,3,5-Trithiacyclohexane, Anal. Chem. 74(21): 5538-5543 (2002).
[23] Taki M., Hattori H., Osako T., Nagatomo S., Shiro M., Kitagawa T., Itoh S., Model complexes of the active site of galactose oxidase. Effects of the metal ion binding sites, Inorg. Chim. Acta 357(11): 3369-3381 (2004).
[24] Neuba A. , Rohrmüller M., Holscher R., Schmidt W. G., Henkel G., A panel of peralkylated sulfur–guanidine type bases: Novel pro-ligands for use in biomimetic coordination chemistry, Inorg. Chim. Acta 430: 225-238(2015).
[25] Dehghani-Firouzabadi A.A., Motevaseliyan F., Synthesis and characterization of four new unsymmetrical potentially pentadentate Schiff base ligands and related Zn(II) and Cd(II) complexes, Eur. J. Chem.5(4): 635-638 (2014).
[26] Dehghani-Firouzabadi A.A., Kargar H., Eslaminejad S., Notash B., Synthesis and characterization of a thioether Schiff base ligand and its metal complexes and crystal structure determination of the nickel(II) complex, J. Coord.Chem. 68(24): 4345-4354 (2015).
[27] Dehghani-Firouzabadi A. A., Sobhani M., Notash B., Synthesis and characterization of metal complexes with NOS unsymmetrical tridentate Schiff base ligand. X-ray crystal structures determination of nickel(II) and copper(II) complexes, Polyhedron 119: 49-54(2016).
[28] Kuan W., Ghang H., Horng Y., Mononuclear zinc(II) and mercury(II) complexes of Schiff bases derived from pyrrolealdehyde and cysteamine containing intramolecular NH⋯S hydrogen bonds, J. Organomet. Chem. 694(13): 2085-2091 (2009 ).
[29] Khandara A. A., Cardin C., Hosseini-Yazdi S. A., McGrady J., Abedi M., Zarei S. A., Gan Y., Nickel(II) and copper(II) complexes of Schiff base ligands containing N4O2 and N4S2 donors with pyrrole terminal binding groups: Synthesis, characterization, X-ray structures, DFT and electrochemical studies, Inorg. Chim. Acta 363(14): 4080-4087 (2010).
[30] Dehghani-Firouzabadi A. A., Firouzmandi S., Synthesis and Characterization of a New Unsymmetrical Potentially Pentadentate Schiff Base Ligand and Related Complexes with Manganese(II), Nickel(II), Copper(II), Zinc(II) and Cadmium(II), J. Braz. Chem. Soc. 28(5): 768-774 (2017).
[31] Geary W. J., The use of conductivity measurements in organic solvents for the characterisation of coordination compounds, Coord. Chem. Rev. 7(1): 81-122 (1971).
[1] Reger T. S., Janda K. D., Polymer-Supported (Salen)Mn Catalysts for Asymmetric Epoxidation:  A Comparisonbetween Soluble and Insoluble Matrices, J. Am. Chem. Soc. 122(29): 6929-6934 (2000).
[2] Nakajima K., Ando Y., Mano H., Kojima M., Photosubstitution reactivity, crystal structures, and electrochemistry of ruthenium (II)(III) complexes containing tetradentate (O2N2, S2N2, and P2N2) Schiff base ligands, Inorg. Chim. Acta 274(2):  184-191 (1998).
[3] Brewer G., Kamaras P., May L., Prytkov S., Rapta M., Synthesis and structural characterization of metal complexes of an unsymmetric N3O tetradentate Schiff base ligand, Inorg. Chim. Acta 279(1): 111-115 (1998).
[4] Yam V. W., Lo K. K., Luminescent polynuclear d10 metal complexes, Chem. Soc. Rev. 28: 323-334 (1999).
[5] McMillin D. R., McNett K. M., Photoprocesses of copper complexes that bind to DNA, Chem. Rev. 98(3): 1201-1220 (1998).
[6] Akbar Ali M., Mirza A. H., Ting W. Y., Haniti M., Hamid S. A., Bernhardt P. V., Butcher R. J., Mixed-ligand nickel(II) and copper(II) complexes of tridentate ONS and NNS ligands derived from S-alkyldithiocarbazates with the saccharinate ion as a co-ligand, Polyhedron 48(1): 167-173 (2012).
[7] Manikandan R., Viswnathamurthi P., Coordination behavior of ligand based on NNS and NNO donors with ruthenium(III) complexes and their catalytic and DNA interaction studies, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 97: 864-870 (2012).
[8] Shafaatian B., Soleymanpour A., Oskouei N. K., Notash B., Rezvani S. A., Synthesis, crystal structure, fluorescence and electrochemical studies of a new tridentate Schiff base ligand and its nickel(II) and palladium(II) complexes, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 128: 363-369 (2014).
[9] Hosseini-Monfared H., Kheirabadi S., Asghari-Lalami N., Mayer P., Dioxo- and oxovanadium(V) complexes of biomimetic hydrazone ONO and NNS donor ligands: Synthesis, crystal structure and catalytic reactivity, Polyhedron 30(8): 1375-1384 (2011).
[10] Chang S., Karambelkar V. V., Sommer R. D., Rheingold A. L., Goldberg D. P., New Monomeric Cobalt(II) and Zinc(II) Complexes of a Mixed N,S(alkylthiolate) Ligand:  Model Complexes of (His)(His)(Cys) Metalloprotein Active Sites, Inorg. Chem.41(2): 239-248 (2002).
[11] Karahan A., Karabulut S., Dal H., Kurtaran R., Leszczynski J., Experimental and theoretical investigation of a novel mononuclear copper(II) azido compound with tridentate (NNO) Schiff base, J. Mol. Struct.1093: 1-7 (2015).
[12] Singh R., Banerjee A., Rajak K. K., Iron(III) complexes using NNS reduced Schiff bases and NNOS coordinating tetradentate ligands: Synthesis, structure and catecholase activity, Inorg. Chim. Acta 363(12): 3131-3138(2010).
[13] Jana S., Jana M. S., Biswas S., Sinha C., Mondal T. K., Synthesis, electronic structure and catalytic activity of ruthenium-iodo-carbonyl complexes with thioether containing NNS donor ligand, J. Mol. Struct.1065-1066: 52-60 (2014).
[14] Kim S., Ginsbach J. W., Billah A. I., Siegler M. A., Moore C. D., Solomon E. I., Karlin K. D., Tuning of the Copper–Thioether Bond in Tetradentate N3S(thioether) Ligands; O–O Bond Reductive Cleavage via a [CuII2(μ-1,2-peroxo)]2+/[CuIII2(μ-oxo)2]2+ Equilibrium, J. Am. Chem. Soc. 136(22): 8063-8071 (2014).
[15] Kalita M., Bhattacharjee T., Gogoi P., Barman P., Kalita R. D., Synthesis, characterization, crystal structure and bioactivities of a new potential tridentate (ONS) Schiff base ligand N-[2-(benzylthio) phenyl] salicylaldimine and its Ni(II), Cu(II) and Co(II) complexes, Polyhedron 60: 47-53 (2013).
[16] یگانهفعال،علی؛موجدیان،مریم؛ کلهر،مهدی؛ عطاران، عبدالمحمد؛  تبارکی، رضا؛ تهیه مشتق تازه­ای از بازشیف تیوفن تتراهیدروبنزو و کاربرد آن در اندازه­گیری فلوئورید در خمیردندان به عنوان یک حسگر تازه فلورسانی فلوئورید، نشریهشیمیومهندسیشیمیایران، (3) 35: 65 تا 75 (1395).
[17] Brand U., Burth R., Vahrenkamp H., Design of Trigonal-Bipyramidal ZnN3S2 Complexes, Inorg. Chem.35(4): 1083-1086 (1996).
[18] Zhang Z., Martell A. E., Motekaitis R. J., Fu L., Synthesis of pentadentate mixed NS dithiolate chelating ligands derived from heterocycles and 2-mercaptoethylamines, Tetrahedron lett.40(25): 4615-4618(1999).
[19] Chandra S., Gupta K., Chromium(III), manganese(II), iron(III), cobalt(II), nickel(II) and copper(II) complexes with a pentadentate, 15-membered new macrocyclic ligand, Trans. Met. Chem.27(2): 196-199 (2002).
[20] Ganjali M. R., Pourjavid M. R., Rezapour M., Haghgoo S., Novel samarium(III) selective membrane sensor based on glipizid, Sens. Actuators B: Chemical 89(1-2): 21-26 (2003).
[21] Ganjali M. R., Rahimi M., Maddah B., Moghimi A., Borhani S., An Eu(III) Sensor Based on N,N-Diethyl-N-(4-hydroxy-6-methylpyridin-2-yl)guanidine, Anal. Sci.20(10): 1427-1431 (2004).
[22] Shamsipur M., Yousefi M., Hosseini M., Ganjali M. R., Lanthanum(III) PVC Membrane Electrodes Based on 1,3,5-Trithiacyclohexane, Anal. Chem. 74(21): 5538-5543 (2002).
[23] Taki M., Hattori H., Osako T., Nagatomo S., Shiro M., Kitagawa T., Itoh S., Model complexes of the active site of galactose oxidase. Effects of the metal ion binding sites, Inorg. Chim. Acta 357(11): 3369-3381 (2004).
[24] Neuba A. , Rohrmüller M., Holscher R., Schmidt W. G., Henkel G., A panel of peralkylated sulfur–guanidine type bases: Novel pro-ligands for use in biomimetic coordination chemistry, Inorg. Chim. Acta 430: 225-238(2015).
[25] Dehghani-Firouzabadi A.A., Motevaseliyan F., Synthesis and characterization of four new unsymmetrical potentially pentadentate Schiff base ligands and related Zn(II) and Cd(II) complexes, Eur. J. Chem.5(4): 635-638 (2014).
[26] Dehghani-Firouzabadi A.A., Kargar H., Eslaminejad S., Notash B., Synthesis and characterization of a thioether Schiff base ligand and its metal complexes and crystal structure determination of the nickel(II) complex, J. Coord.Chem. 68(24): 4345-4354 (2015).
[27] Dehghani-Firouzabadi A. A., Sobhani M., Notash B., Synthesis and characterization of metal complexes with NOS unsymmetrical tridentate Schiff base ligand. X-ray crystal structures determination of nickel(II) and copper(II) complexes, Polyhedron 119: 49-54(2016).
[28] Kuan W., Ghang H., Horng Y., Mononuclear zinc(II) and mercury(II) complexes of Schiff bases derived from pyrrolealdehyde and cysteamine containing intramolecular NH⋯S hydrogen bonds, J. Organomet. Chem. 694(13): 2085-2091 (2009 ).
[29] Khandara A. A., Cardin C., Hosseini-Yazdi S. A., McGrady J., Abedi M., Zarei S. A., Gan Y., Nickel(II) and copper(II) complexes of Schiff base ligands containing N4O2 and N4S2 donors with pyrrole terminal binding groups: Synthesis, characterization, X-ray structures, DFT and electrochemical studies, Inorg. Chim. Acta 363(14): 4080-4087 (2010).
[30]Dehghani-Firouzabadi A. A., Firouzmandi S., Synthesis and Characterization of a New Unsymmetrical Potentially Pentadentate Schiff Base Ligand and Related Complexes with Manganese(II), Nickel(II), Copper(II), Zinc(II) and Cadmium(II), J. Braz. Chem. Soc. 28(5): 768-774 (2017).
[31] Geary W. J., The use of conductivity measurements in organic solvents for the characterisation of coordination compounds, Coord. Chem. Rev. 7(1): 81-122 (1971).