Synthesis, Characterization and Single Crystal X–ray Crystallography of Nd(III) and Pr(III) Complexes with the Tridentate Schiff Base Ligand N'–(1–(pyridin–2–yl)ethylidene)nicotinohydrazide
Abstract
The use of N'–(1–(pyridin–2–yl)ethylidene)nicotinohydrazide (HL) in lanthanide(III) chemistry has yielded one mononuclear and one dinuclear complexes. The 1:1 Nd(NO3)3.6H2O or Pr(CH3COO)3.6H2O/HL in methanol afforded the complexes [Nd (HL)2(NO3)2(H2O)2].(NO3) (1) and {[Pr(L)(h2–OOCCH3)(H2O)](h1:h2:m–OOCCH3)2[Pr (L)(h2–OOCCH3)(H2O)]} (2). The structures of the complexes were solved by single crystal X–ray crystallography. In the mononuclear complex, the Nd3+ atom is coordinated by two neutral molecules of ligand acting in tridentate fashion, two nitrate anions acting in bidentate manner and two coordinated water molecules yielding a twelve–coordinated Nd atom. In the complex (2) the Pr3+ atoms are doubly bridged by two acetates anions and each metal ion is coordinated by one tridentate monodeprotonated molecule ligand, one bidentate acetate group and one coordinated water molecule. Each Pr3+ atom is nine–coordinated with an environment best described as a tricapped prismatic geometry. Complex 1 crystallizes in the monoclinic space group C2/c with the following parameters: a = 22.7657(8) Å, b = 8.4276(3) Å, c = 18.0831(7) Å, b = 114.851(2)°, V = 3148.2(2) Å3, Z = 4, R1 = 0.032, wR2 = 0.098. Complex 2 crystallizes in the monoclinic space group P21/n with the following parameters: a = 11.5388(6) Å, b = 14.1087(8) Å, c = 12.2833(6) Å, b = 102.211(2)°, V = 1954.45(18) Å3, Z = 2, R1 = 0.029, wR2 = 0.066. The supramolecular structures are consolidated by multiple hydrogen bonds.
References
A. Jayamani, M. Sethupathi, S.O. Ojwach and N. Sengottuvelan, Synthesis, characterization and biomolecular interactions of Cu(II) and Ni(II) complexes of acyclic Schiff base ligand, Inorganic Chemistry Communications 84 (2017), 144-149. https://doi.org/10.1016/j.inoche.2017.08.013
A.M. Kaczmarek, P.W.A. Porebski, T. Mortier, F. Lynen, R.V. Deun and K.V. Hecke, Near-infrared luminescence and RNA cleavage ability of lanthanide Schiff base complexes derived from N,N′-bis(3-methoxysalicylidene)ethylene-1,2-diamine ligands, Journal of Inorganic Biochemistry 163 (2016), 194-205. https://doi.org/10.1016/j.jinorgbio.2016.07.017
P.R. Shakya, A.K. Singh and T.R. Rao, Homo dinuclear lanthanide(III) complexes of a mesogenic Schiff-base, N,N′-di-(4-decyloxysalicylidene)-1′,6′-diaminohexane: Synthesis and characterization, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 79 (2011), 1654-1659. https://doi.org/10.1016/j.saa.2011.05.030
J. Nawrocka and V. Patroniak, The template synthesis and characterization of new mono- and dinuclear Schiff base complexes of lanthanide(III) ions, Journal of Alloys and Compounds 380 (2004), 159-162. https://doi.org/10.1016/j.jallcom.2004.03.079
M. Fondo, A.M. García-Deibe, N. Ocampo, J. Sanmartín and M.R. Bermejo, Influence of some reaction conditions on the obtaining of tetra- and dinuclear zinc complexes of some Schiff bases derived from 2,6-diformyl-4-alkyl-phenols, Polyhedron 27 (2008), 2585-2594. https://doi.org/10.1016/j.poly.2008.05.016
F. Benetollo, G. Bombieri, A.M. Adeyga, K.K. Fonda, W.A. Gootee, K.M. Samaria and L.M. Vallarino, Lanthanide(III) complexes of six-nitrogen-donor macrocyclic ligands with benzyl-type peripheral substituents, and crystal structure of [La(NO3)2(H2O)(C36 H38N6)](NO3)(H2O), Polyhedron 21 (2002), 425-433. https://doi.org/10.1016/S0277-5387(01)01008-7
F. Gao, Y.-Q. Zhang, W. Sun, H. Liu and X. Chen, Syntheses, structures and magnetic properties of macrocyclic Schiff base-supported homodinuclear lanthanide complexes, Dalton Transactions 47 (2018), 11696-11704. https://doi.org/10.1039/C8DT02243G
B.S. Sran, S. Sharma, F. Pointillart, O. Cador and G. Hundal, Field-induced single molecular magnetism and photoluminescence in rare cocrystals of isomorphic lanthanide(III) coordination compounds with fully substituted pyridine-4-carboxamide ligand, Inorganic Chemistry 59 (2020), 9227-9238. https://doi.org/10.1021/acs.inorgchem.0c01134
U. Casellato, S. Tamburini, P. Tomasin and P.A. Vigato, Cyclic and acyclic compartmental Schiff bases, their reduced analogues and related mononuclear and heterodinuclear complexes, Inorganica Chimica Acta 357 (2004), 4191-4207. https://doi.org/10.1016/j.ica.2004.06.007
I.A. Kahwa, J. Selbin, C.J. O’Connor, J.W. Foise and G.L. McPherson, Magnetic and luminescence characteristics of dinuclear complexes of lanthanides and a phenolic schiff base macrocyclic ligand, Inorganica Chimica Acta 148 (1988), 265-272. https://doi.org/10.1016/S0020-1693(00)87513-1
M.T. Kaczmarek, M. Zabiszak, M. Nowak and R. Jastrzab, Lanthanides: Schiff base complexes, applications in cancer diagnosis, therapy, and antibacterial activity, Coordination Chemistry Reviews 370 (2018), 42-54. https://doi.org/10.1016/j.ccr.2018.05.012
R. Jastrzab, M.T. Kaczmarek, M. Nowak, A. Trojanowska and M. Zabiszak, Complexes of polyamines and their derivatives as living system active compounds, Coordination Chemistry Reviews 351 (2017), 32-44. https://doi.org/10.1016/j.ccr.2017.05.001
S.-G. Wu, Y.-Y. Peng, Y.-C. Chen, J.-L. Liu and M.-L. Tong, Magnetic dynamics of an open-ring tridysprosium complex employing mixed ligands, Dalton Transactions 49 (2020), 14140-14147. https://doi.org/10.1039/D0DT02698K
M.T. Benson, T.R. Cundari, L.C. Saunders and S.O. Sommerer, Synthesis, structure, computational studies, and magnetic properties of a ten-coordinate gadolinium(III) complex, Inorganica Chimica Acta 258 (1997), 127-130. https://doi.org/10.1016/S0020-1693(97)05541-2
X. Liu and J.-R. Hamon, Recent developments in penta-, hexa- and heptadentate Schiff base ligands and their metal complexes, Coordination Chemistry Reviews 389 (2019), 94-118. https://doi.org/10.1016/j.ccr.2019.03.010
W. Radecka-Paryzek, I. Pospieszna-Markiewicz and M. Kubicki, Self-assembled two-dimensional salicylaldimine lanthanum(III) nitrate coordination polymer, Inorganica Chimica Acta 360 (2007), 488-496. https://doi.org/10.1016/j.ica.2006.07.071
B. Cristóvão, D. Osypiuk, B. Miroslaw and A. Bartyzel, Heterometallic di- and trinuclear CuIILnIII (LnIII = La, Ce, Pr, Nd) complexes with an alcohol-functionalized compartmental Schiff base ligand: Syntheses, crystal structures, thermal and magnetic studies, Polyhedron 188 (2020), 114703. https://doi.org/10.1016/j.poly.2020.114703
T. Fatima, Imtiaz-ud-Din, A. Akbar, M.S. Anwar and M.N. Tahir, Six new dinuclear Schiff base complexes of Cu(II)/Ln(III) system: Synthesis, characterization and magnetic studies, Journal of Molecular Structure 1184 (2019), 462-467. https://doi.org/10.1016/j.molstruc.2019.02.037
B. Cristóvão, D. Osypiuk, B. Miroslaw and A. Bartyzel, Syntheses, crystal structures, thermal and magnetic properties of new heterotrinuclear CuII–LnIII–CuII complexes incorporating N2O4-donor Schiff base ligands, Polyhedron 144 (2018), 225-233. https://doi.org/10.1016/j.poly.2018.01.023
G. Zhang, X. Xia, J. Xu, H. Wu, L. Xia, Y. Qu and X. Han, Synthesis, structure and property of two d-f heteronuclear Eu-TM (TM = Zn and Cd) complexes with open-chain ether Schiff base ligand, Journal of Molecular Structure 1226 (2021), 129337. https://doi.org/10.1016/j.molstruc.2020.129337
B. Yuan, F. Wang, J. Tao, M. Li and X. Yang, Self-assembly of one visible and NIR luminescent Sm(III) coordination polymer with flexible Schiff base ligand, Inorganica Chimica Acta 490 (2019), 24-28. https://doi.org/10.1016/j.ica.2019.02.019
M.A. Singh-Wilmot, I.A. Kahwa, A.J.P. White, D.J. Williams and A.J. Lough, Tunable electronic interactions in small lanthanide(III) nanoclusters: The comparative effects of OH− and O2− supramolecular glues on europium(III)-to-dysprosium(III) energy transfer, Polyhedron 29 (2010), 270-279. https://doi.org/10.1016/j.poly.2009.08.024
M. Kozłowski, R. Kierzek, M. Kubicki and W. Radecka-Paryzek, Metal-promoted synthesis, characterization, crystal structure and RNA cleavage ability of 2,6-diacetylpyridine bis(2-aminobenzoylhydrazone) lanthanide complexes, Journal of Inorganic Biochemistry 126 (2013), 38-45. https://doi.org/10.1016/j.jinorgbio.2013.05.005
J.-H. Jia, Q.-W. Li, Y.-C. Chen, J.-L. Liu and M.-L. Tong, Luminescent single-molecule magnets based on lanthanides: Design strategies, recent advances and magneto-luminescent studies, Coordination Chemistry Reviews 378 (2019), 365-381. https://doi.org/10.1016/j.ccr.2017.11.012
N.C. Anastasiadis, N. Lalioti, A. Terzis, V. Psycharis, C.P. Raptopoulou and S.P. Perlepes, The N-(2-carboxyphenyl)salicylideneimine ligand in 4f-metal chemistry: A unique neodymium(III) chain containing the singly deprotonated, zwitterionic form of the ligand, Inorganic Chemistry Communications 51 (2015), 118-121. https://doi.org/10.1016/j.inoche.2014.11.020
Z.A. Taha and A.K. Hijazi, Structural and photophysical properties of lanthanide complexes with N’-(2-methoxybenzylidene)-2-pyridinecarbohydrazide Schiff base ligand: Catalyzed oxidation of anilines with hydrogen peroxide, Journal of Molecular Structure 1238 (2021), 130451. https://doi.org/10.1016/j.molstruc.2021.130451
H.A.R. Pramanik, C. Chanda, P.C. Paul, C.R. Bhattacharjee, S.K. Prasad and D.S.S. Rao, Novel tris-buffer based Schiff base bearing long flexible alkoxy arm and its lanthanide complexes: Mesomorphism and photoluminescence, Journal of Molecular Structure 1180 (2019), 472-479. https://doi.org/10.1016/j.molstruc.2018.12.014
S.G. Dogaheh, J. Soleimannejad and E.C. Sanudo, Asymmetric Schiff base ligand enables synthesis of fluorescent and near-IR emitting lanthanide compounds, Journal of Molecular Structure 1219 (2020), 129060. https://doi.org/10.1016/j.molstruc.2020.129060
G.M. Sheldrick, SHELXT–Integrated space-group and crystal-structure determination, Acta Crystallographica Section A 71 (2015), 3-8. https://doi.org/10.1107/S2053273314026370
G.M. Sheldrick, Crystal structure refinement with SHELXL, Acta Crystallographica Section C 71 (2015), 3-8. https://doi.org/10.1107/S2053229614024218
L.J. Farrugia, WinGX and ORTEP for Windows: an update, Journal of Applied Crystallography 45 (2012), 849-854. https://doi.org/10.1107/S0021889812029111
B. Benmerad, K. Aliouane, N. Rahahlia, A. Guehria-Laïdoudi, S. Dahaoui and C. Lecomte, Studies of two lanthanide coordination polymers built up from dinuclear units, Journal of Rare Earths 31 (2013), 85-93. https://doi.org/10.1016/S1002-0721(12)60240-3
Z.A. Taha, A.M. Ajlouni, W.A. Momani and A.A. Al-Ghzawi, Syntheses, characterization, biological activities and photophysical properties of lanthanides complexes with a tetradentate Schiff base ligand, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 81 (2011), 570-577. https://doi.org/10.1016/j.saa.2011.06.052
T. Madanhire, H. Davids, M.C. Pereira, E.C. Hosten and A. Abrahams, Synthesis, characterisation and anticancer activity screening of lanthanide(III) acetate complexes with benzohydrazone and nicotinohydrazone ligands, Polyhedron 184 (2020), 114560. https://doi.org/10.1016/j.poly.2020.114560
G.B. Deacon and R.J. Phillips, Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination, Coordination Chemistry Reviews 33 (1980), 227-250. https://doi.org/10.1016/S0010-8545(00)80455-5
Q. Xie, S. Li, S. Zhang, D. Zhang, Z. Zhang and J. Hu, The structure and biological activity of tributyltin carboxylates, Acta Chimica Sinica 49 (1991), 723-728. http://sioc-journal.cn/Jwk_hxxb/EN/Y1991/V49/I7/723
J.H. Van Vleck and A. Frank, The effect of second order Zeeman terms on magnetic susceptibilities in the rare earth and iron groups, Physical Reviews 34 (1929), 1494-1496. https://doi.org/10.1103/PhysRev.34.1625
W.J. Geary, The use of conductivity measurements in organic solvents for the characterisation of coordination compounds, Coordination Chemistry Reviews 7 (1971), 81-122. https://doi.org/10.1016/S0010-8545(00)80009-0
D.G. Paschalidis and W.T.A. Harrison, Two mixed-ligand lanthanide–hydrazone complexes: [Pr(NCS)3(pbh)2].H2O and [Nd(NCS)(NO3)(pbh)2(H2O)]NO3.2.33H2O [pbh is N'-(pyridin-2-ylmethylidene)benzohydrazide, C13H11N3O], Acta Crystallographica Section E 72 (2016), 191-195. https://doi.org/10.1107/S2056989015024962
Z.-Y. Pan, J.-H. Chen, J.-F. Lin, X. Xu and Y.-F. Luo, Poly[(acetato-κ2O,O')aqua(μ4-1 H-benzimidazole-5,6-dicarboxylato-κ5N3:O5,O5':O5,O6:O6')praseodymium(III)], Acta Crystallographica Section E 66 (2010), m1302. https://doi.org/10.1107/S1600536810036986
S.-Y. Zhang, Z. Shi, Z. Long-Guan, R.-R. Xu and W.-Q. Pang, Di-μ-acetato-κ3O,O':O'-di-μ-trichloroacetato-κ2O:O'-bis[aqua(trichloroacetato) (1,10-phenanthroline-κ2N,N')praseod ymium(III)] dimethylformamide disolvate, Acta Crystallographica Section E 59 (2003), m142-m144. https://doi.org/10.1107/S1600536803004744
M. Ndiaye-Gueye, M. Dieng, E.I. Thiam, D. Lo, A.H. Barry, M. Gaye and P. Retailleau, Lanthanide(III) complexes with tridentate Schiff base ligand, antioxidant activity and X-ray crystal structures of the Nd(III) and Sm(III) complexes, South African Journal of Chemistry 70 (2017), 8-15. https://doi.org/10.17159/0379-4350/2017/v70a2
Nd.M. Gueye, D. Moussa, E.I. Thiam, A.H. Barry, M. Gaye and P. Retailleau, Crystal structure of bis(acetato-κ2O,O')diaqua[1-(pyridin-2-ylmethylidene-κN)-2-(pyridin-2-yl-κN)hydrazine-κN1]terbium(III) nitrate monohydrate, Acta Crystallographica Section E 73 (2017), 1121-1124. https://doi.org/10.1107/S2056989017009653
Q. Yu, X. Zhou, M. Liu, J. Chrn, Z. Zhou, X. Yin and Y. Cai, Syntheses, characterization, and luminescence of two lanthanide complexes [Ln2(acetate)6(H2O)4]•4H2O (Ln=Tb(1), Sm(2)), Journal of Rare Earths 26 (2008), 178-184. https://doi.org/10.1016/S1002-0721(08)60061-7
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