Skip to main content
Log in

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)]

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

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 26 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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Dharmaraj N, Viswanathamurthi P, Natarajan K (2001) Ruthenium(II) complexes containing bidentate Schiff bases and their antifungal activity. Transit Met Chem 26:105–109

    Google Scholar 

  2. 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

    Article  CAS  Google Scholar 

  3. 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

    Article  Google Scholar 

  4. 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

    Article  CAS  Google Scholar 

  5. Shahabadi N, Ghasemian Z, Hadidi S (2012) Bioinorg Chem Appl 2012:1–9

    Google Scholar 

  6. Cozzi PG (2004) Metal–Salen Schiff base complexes in catalysis: practical aspects. Chem Soc Rev 33:410–421

    Article  CAS  Google Scholar 

  7. 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

    Article  CAS  Google Scholar 

  8. 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

    Article  Google Scholar 

  9. 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

    Article  Google Scholar 

  10. 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

    Article  Google Scholar 

  11. 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

    Article  CAS  Google Scholar 

  12. 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

    Article  CAS  Google Scholar 

  13. 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

    Google Scholar 

  14. 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

    Article  CAS  Google Scholar 

  15. 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

    Article  CAS  Google Scholar 

  16. 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

    Article  CAS  Google Scholar 

  17. 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

    Article  CAS  Google Scholar 

  18. 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

    Article  CAS  Google Scholar 

  19. Hao H, Zhang H (2005) N,N’-bis[4-(dimethylamino)benzylidene]-ethane-1,2-diamine. Acta Crystallogr E61:o4274–o4275

    Google Scholar 

  20. Xiao L, Wang D (2006) N,N’-bis(4-dimethylaminobenzylidene)-ethane-1,2-diamine. Acta Crystallogr E62:o724–o725

    Google Scholar 

  21. 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

    Article  CAS  Google Scholar 

  22. 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

    Article  CAS  Google Scholar 

  23. Agilent (2010) CrysAlisPro-X-ray crystallography data systems software. Oxford Diffraction—Agilent Technologies UK Ltd, Yarnton England

  24. 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

    Google Scholar 

  25. Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr A 64:112–122

    Article  CAS  Google Scholar 

  26. Farrugia LJ (2012) WinGX and ORTEP for windows: an update. J Appl Crystallogr 45:849–854

    Article  CAS  Google Scholar 

  27. 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

    Article  CAS  Google Scholar 

  28. 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

    Article  CAS  Google Scholar 

  29. 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

    Article  CAS  Google Scholar 

  30. 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

    Article  CAS  Google Scholar 

  31. 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

    Article  CAS  Google Scholar 

  32. Al-Shalaan AM, Al-Showiman SS, Al-Najjar M (1986) Isomerization of imines in platinum–imine complexes. Inorg Chim Acta 121:127–129

    Article  CAS  Google Scholar 

  33. 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

    Article  CAS  Google Scholar 

  34. 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

    Article  CAS  Google Scholar 

  35. 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

    Article  Google Scholar 

  36. 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

    Article  CAS  Google Scholar 

Download references

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.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Eduardo T. de Almeida.

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-014-9824-y

Keywords

Navigation