Abstract
Five new complexes of general formula [PdX2(p-diben)], where p-diben = N,N′-bis(4-dimethylaminobenzylidene)ethane-1,2-diamine) (1) and X = Cl (2), Br (3), I (4), N3 (5), or CNO (6), were synthesized and characterized by physicochemical and spectroscopic methods. The crystal structure of compound (5) was determined by single-crystal X-ray diffraction. Complexes 2–6 were characterized as N,N-chelated products. The crystal structure confirmed this formulation for [Pd(N3)2(p-diben)], besides showing the isomerism inversion of one of the C=N bonds, caused by Pd(II) coordination.
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Dharmaraj N, Viswanathamurthi P, Natarajan K (2001) Ruthenium(II) complexes containing bidentate Schiff bases and their antifungal activity. Transit Met Chem 26:105–109
Khalaji AD, Hadadzadeh H, Fejfarova K, Dusek M (2010) Metal-dependent assembly of a tetranuclear copper(II) complex versus a 1D chain coordination polymer of cobalt(III) complex with N2O2-chelating Schiff-base ligand: synthesis, characterization and crystal structures. Polyhedron 29:807–812
Daniel VP, Murukan B, Kumari BS, Mohanan K (2008) Synthesis, spectroscopic characterization, electrochemical behavior, reactivity and antibacterial activity of some transition metal complexes with 2-(N-salicylideneamino)-3-carboxyethyl-4,5-dimethylthiophene. Spectrochim Acta A Mol Biomol Spectrosc 70:403–410
Neelakantan MA, Marriappan SS, Dharmaraja J, Jeyakumar T, Muthukumaran K (2008) Spectral, XRD, SEM and biological activities of transition metal complexes of polydentate ligands containing thiazole moiety. Spectrochim Acta A Mol Biomol Spectrosc 71:628–635
Shahabadi N, Ghasemian Z, Hadidi S (2012) Bioinorg Chem Appl 2012:1–9
Cozzi PG (2004) Metal–Salen Schiff base complexes in catalysis: practical aspects. Chem Soc Rev 33:410–421
Keypour H, Jamshidi AH, Rezaeivala M, Valencia L (2013) Synthesis and characterization of mononuclear and dimeric Ni(II), Cu(II) and Cd(II) Schiff base complexes with two new asymmetrical tripodal amines. Crystal structures of Ni(II) and Cd(II) complexes and their antibacterial studies. Polyhedron 52:872–878
Ali MA, Mirza AH, Butcher RJ, Tarafder MTH, Keat TB, Ali AM (2002) Biological activity of palladium(II) and platinum(II) complexes of the acetone Schiff bases of S-methyl- and S-benzyldithiocarbazate and the X-ray crystal structure of the [Pd(asme)2] (asme = anionic form of the acetone Schiff base of S-methyldithiocarbazate) complex. J Inorg Biochem 92:141–148
Lee SK, Tan KW, Ng SW, Ooi KK, Ang KP, Abdah MA (2013) Zinc (II) complex with a cationic Schiff base ligand: synthesis, characterization, and biological studies. Spectrochim Acta A Mol Biomol Spectrosc 121:101–108
Jayamani A, Thamilarasan V, Sengottuvelan N, Manisankar P, Kang SK, Kim YI, Ganesan V (2013) Synthesis of mononuclear copper(II) complexes of acyclic Schiff’s base ligands: spectral, structural, electrochemical, antibacterial, DNA binding and cleavage activity. Spectrochim Acta A Mol Biomol Spectrosc 122:365–374
Ma ZY, Qiao X, Xie CZ, Shao J, Xu JY, Qiang ZY, Lou JS (2012) Activities of a novel Schiff base copper(II) complex on growth inhibition and apoptosis induction toward MCF-7 human breast cancer cells via mitochondrial pathway. J Inorg Biochem 117:1–9
Naeimi H, Moradian M (2008) Alumina-supported metal(II) Schiff base complexes as heterogeneous catalysts in the high-regioselective cleavage of epoxides to halohydrins by using elemental halogen. Polyhedron 27:3639–3645
Grivani G, Akherati A (2013) Polymer-supported bis(2-hydroxyanil) acetylacetonatomolybdenyl Schiff base catalyst as effective, selective and highly reusable catalyst in epoxidation of alkenes. Inorg Chem Commun 28:90–93
Bhunia S, Koner S (2011) Tethering of nickel(II) Schiff-base complex onto mesoporous silica: an efficient heterogeneous catalyst for epoxidation of olefins. Polyhedron 30:1857–1864
Tamami B, Ghasemi S (2011) Modified crosslinked polyacrylamide anchored Schiff base–cobalt complex: a novel nano-sized heterogeneous catalyst for selective oxidation of olefins and alkyl halides with hydrogen peroxide in aqueous media. Appl Catal A: Gen 393:242–250
Rayati S, Zakavi S, Koliaei M, Wojtczak A, Kozakiewicz A (2010) Electron-rich salen-type Schiff base complexes of Cu(II) as catalysts for oxidation of cyclooctene and styrene with tert-butylhydroperoxide: a comparison with electron-deficient ones. Inorg Chem Commun 13:203–207
Wakatsuki Y, Yamazaki H, Grutsch PA, Santhanam M, Kutal C (1985) Study of intramolecular sensitization and other excited-state pathways in orthometallated azobenzene complexes of palladium(II). J Am Chem Soc 107:8153–8159
Espinet P, Esteruelas MA, Oro LA, Serrani JL, Sola E (1992) Transition metal liquid crystals: advanced materials within the reach of the coordination chemist. Coord Chem Rev 117:215–274
Hao H, Zhang H (2005) N,N’-bis[4-(dimethylamino)benzylidene]-ethane-1,2-diamine. Acta Crystallogr E61:o4274–o4275
Xiao L, Wang D (2006) N,N’-bis(4-dimethylaminobenzylidene)-ethane-1,2-diamine. Acta Crystallogr E62:o724–o725
Bruce MI, Burgun A, Nicholson BK, Parker CR, Skelton BW, White AH (2012) Polarized complexes obtained by regiospecific substitution of a CN group in Ru{C≡CC(CN)=C(CN)2}(dppe)Cp* (Cp*=η-C5Me5). Organometallics 31:4174–4181
Hansen HD, Maitra K, Nelson JH (1999) Chloride substitution reactions of cycloruthenated (R)C-(+)-N,N-dimethyl(1-phenylethyl)amine with pseudohalides: ruthenium atom stereochemistry. Inorg Chem 38:2150–2156
Agilent (2010) CrysAlisPro-X-ray crystallography data systems software. Oxford Diffraction—Agilent Technologies UK Ltd, Yarnton England
Altomare A, Cascarano G, Giacovazzo C, Guagliardi A, Burla MC, Polidori G, Camalli M (1994) SIR92—a program for automatic solution of crystal structures by direct methods. J Appl Crystallogr 27:435
Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr A 64:112–122
Farrugia LJ (2012) WinGX and ORTEP for windows: an update. J Appl Crystallogr 45:849–854
Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA (2008) Mercury CSD 2.0—new features for the visualization of crystal structures. J Appl Crystallogr 41:466–470
Bruno IJ, Cole JC, Kessler M, Luo J, Motherwell WDS, Purkis LH, Smith BR, Taylor R, Cooper RI, Harris SE, Orpen AG (2004) Retrieval of crystallographically-derived molecular geometry information. J Chem Inf Comput Sci 44:2133–2144
Souza RA, Mauro AE, Netto AVG, Cunha GA, De Almeida ET (2011) Synthesis, characterization, and thermal behavior of palladium(II) coordination compounds containing isonicotinamide. J Therm Anal Calorim 106:375–378
Chattopadhyay S, Bhar K, Das S, Satapathi S, Fun H, Mitra P, Ghosh BK (2010) Synthesis, molecular and crystalline architectures, and properties of novel bis(bidentate) and bis(tridentate) Schiff base bridged dinuclear mercury(II) pseudohalides: control of coordination numbers by varying denticities. Polyhedron 29:1667–1675
Sain S, Saha R, Mostafa G, Fleck M, Bandyopadhyay D (2012) Synthesis and crystal structure of three new copper(II) complexes with a tridentate amine and its Schiff bases. Polyhedron 31:82–88
Al-Shalaan AM, Al-Showiman SS, Al-Najjar M (1986) Isomerization of imines in platinum–imine complexes. Inorg Chim Acta 121:127–129
Al-Najjar IM (1988) A comparative study of neighboring group effects on the isomerization of imines in platinum-imine complexes by 1H, 13C, 31P and 198Pt NMR spectroscopy. Spectrochim Acta 44A:57–62
Zilberg S, Haas Y (2003) Isomerization around a C=N double bond and a C=C double bond with a nitrogen atom attached: thermal and photochemical routes. Photochem Photobiol Sci 2:1256–1263
Albert J, Granell J, Luque A, Font-Bardía M, Solans X (1997) Steric and electronic effects on E/Z composition of exocyclic cyclopalladated N-benzylideneamines. J Organmet Chem 545–546:131–137
Bakkar M, Monshi M, Warad I, Siddiqui M, Bahajaj A (2010) 1H 13C NMR investigation of E/Z-isomerization around C=N bond in the trans-alkene-Pt(II)imine complexes of some ketimines and aldimines. J Saudi Chem Soc 14:165–174
Acknowledgments
We thank CAPES, CNPq, FINEP, and FAPEMIG for financial support and scholarship: Sarto LE (FAPEMIG), Landre IMR (FAPEMIG), and Bozza GF (CAPES). We thank LabCri-UFMG for the single-crystal diffraction measurements and Prof. Dr. Carlos B. Pinheiro and Prof. Dr. Nilvado L. Speziali for support during the single-crystal diffraction measurements.
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Sarto, L.E., Landre, I.M.R., Bozza, G.F. et al. Synthesis and characterization of palladium(II) complexes [PdX2(p-diben)] (X = Cl, Br, I, N3, or NCO; p-diben = N,N′-bis(4-dimethylaminobenzylidene)ethane-1,2-diamine): crystal structure of [Pd(N3)2(p-diben)]. Transition Met Chem 39, 495–500 (2014). https://doi.org/10.1007/s11243-014-9824-y
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DOI: https://doi.org/10.1007/s11243-014-9824-y