Skip to main content
Log in

Synthesis and Characterization of New Tetradentate Ligands

  • Research Paper
  • Published:
Iranian Journal of Science and Technology, Transactions A: Science Aims and scope Submit manuscript

Abstract

Four new tetradentate ligands [14] have been prepared by a 1:2 molar condensation of an aromatic dialdehyde (terephthalaldehyde) with thiophen-2-ylmethanamine, 2-(thiophen-2-yl)ethanamine, pyridin-2-ylmethanamine and 2-(pyridin-2-yl)ethanamine. The ligands were characterised on the basis of their elemental analysis, IR spectroscopies, 1H, 13C NMR, ESI-mass spectrometry and for ligands 1, 2 and 4 also by X-ray diffraction. The crystal structures reveal that the ligands exist as discrete molecules with an average C–N bond distance of 1.2656 Å which is consistent with C=N double bonding.

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.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2

Similar content being viewed by others

References

  • Al-Allaf TAK, Sheet AZM (1995) Platinum group metal Schiff base complexes-I. Platinum complexes. Polyhedron 14(2):239–248

    Article  Google Scholar 

  • Al-Allaf TAK, Rashan LJ, Abu-Surrah AS, Fawzi R, Steimann M (1998) Chemical properties and cytotoxic activity of complexes of platinum(II) and palladium(II) containing dmso and various anions; synthesis and structural characterization of [Pt(dmso)2{O2(CO)2CCH2CH2CH2}]. Transit Met Chem 23:403–406

    Article  Google Scholar 

  • Bailey CT, Linsesky GCJ (1985) Synthesis of organometallic palladium complexes: an undergraduate experiment. J Chem Edu 62:896

    Article  Google Scholar 

  • Bekhit AA, El-Sayed OA, Al-Allaf TAK, Aboul-Enein HY, Kunhi M, Pulicat SM, Al-Hussain K, Al-Khodairy F, Arif J (2004) Synthesis, characterization and cytotoxicity evaluation of some new platinum(II) complexes of tetrazolo[1,5-a]quinolines. Eur J Med Chem 39(6):499–505

    Article  Google Scholar 

  • Carey DT, Cope-Eatough EK, Vilaplana-Mafe E, Mair FS, Pritchard RG, Warren JE, Woods RJ (2003) Structures and reactions of monomeric and dimeric lithium diazapentadienyl complexes with electrophiles: synthesis of α-C,C′-dialkyl-β-diimines, and dissolution-reversible synthesis of an α-alkoxylithium-β-diimine. Dalton Trans 6:1083–1093

    Article  Google Scholar 

  • Chatt J, Vallarino LM, Venanzi LM (1957) Olefin co-ordination compounds. Part V. Some diene complexes of palladium(II) and their alkoxy-derivatives. J Chem Soc 3413–3416. doi:10.1039/JR9570003413

  • Chiririwa H, Moss JR, Su H, Hendricks D, Meijboom R (2011a) 1,4-bis[(2-Pyridylethyl)iminomethyl]benzene. Acta Crystallogr Sect E E67:o921

    Article  Google Scholar 

  • Chiririwa H, Meijboom R, Omondi B (2011b) 2-(Thiophen-2-yl)-N-(4-{(E)-[2-(thiophen-2yl)ethyl]iminomethyl}benzylidene)ethanamine. Acta Crystallogr Sect E E67:o922

    Article  Google Scholar 

  • Chiririwa H, Moss JR, Hendricks D, Meijboom R (2012) 1-(Thiophen-2-yl)-N-(4-{(E)-[(thiophen-2-yl)methyl]iminomethyl}benzylidene)methanamine. Acta Crystallogr Sect E E68:o3137

    Article  Google Scholar 

  • Derrah EJ, Zhang H, Nikolcheva LG, Vogels CM, Decken A, Westcott SA (2003) Novel reactivity of unconjugated diimines with [PtCl2(coe)]2 (coe = cis-cyclooctene). Inorg Chem Commun 6(8):1086–1090

    Article  Google Scholar 

  • Drew D, Doyle JR (1990) Reagents for transition metal complex and organometallic syntheses. Inorg Synth 28:346

    Google Scholar 

  • Hamaker CG, Halbach DP (2006) Synthesis, structure, and characterization of some ruthenium arene complexes of N-(arylmethylene)-2-(methylthio)anilines and 2-(methylthio)aniline. Inorg Chim Acta 359:846–852

    Article  Google Scholar 

  • Johnson LK, Killian CM, Brookhart M (1995) New Pd(II)- and Ni(II)-based catalysts for polymerization of ethylene and. alpha.-olefins. J Am Chem Soc 117:6414–6415

    Article  Google Scholar 

  • Krautler B (1987) The porphinoids-versatile biological catalyst molecules. Chimica 41:277–292

    Google Scholar 

  • Lapido FT, Anderson GK (1994) Convenient method for the synthesis of chloro-bridged methyl- and acetylpalladium(II) dimers. J Organomet Chem 13:303–306

    Article  Google Scholar 

  • McDermott JX, White JF, Whitesides GM (1976) Thermal decomposition of bis(phosphine)platinum(II) metallocycles. J Am Chem Soc 98:6521–6528

    Article  Google Scholar 

  • Mingxing Q, Mei W, Zhou BR (2001) Ethylene oligomerization by cobalt(II) diimine complexes/EAO. Appl Catal A Gen 209(1–2):11–15

    Google Scholar 

  • Pascu SI, Coleman KS, Cowley AR, Green MLH, Rees NH (2005) New group 10 complexes of the bulky iminophosphine ligands [Ph2PCH2C(Ph)=N(2,6-R2C6H3)], where R = Me, iPr. New J Chem 29:385–397

    Article  Google Scholar 

  • Price JJ, Williamson AN, Schramm RF, Wayland BB (1972) Palladium(II) and platinum(II) alkyl sulfoxide complexes. Examples of sulfur-bonded, mixed sulfur- and oxygen-bonded, and totally oxygen-bonded complexes. Inorg Chem 11:1280–1284

    Article  Google Scholar 

  • Rulke RE, Ernsting JM, Spek AL, Elsevier CJ, van Leeuwen PWNM, Vrieze K (1993) NMR study on the coordination behavior of dissymmetric terdentate trinitrogen ligands on methylpalladium(II) compounds. Inorg Chem 32:5769–5778

    Article  Google Scholar 

  • Sacconi L, Nannelli P, Camigli U (1965) Five-coordination in some complexes of nickel(II) with schiff bases, formed from salicylaldehydes and N,N-substituted ethylenediamines. II. Inorg Chem 4(7):943–949

    Article  Google Scholar 

  • Sheldrick GM (1997) SHELX97, programme for solving crystal structures. University of Gottingen, Germany

  • Thibault M-H, Lucier BEG, Schurko RW, Fontaine F-G (2009) Synthesis and solid-state characterization of platinum complexes with hexadentate amino- and iminophosphine ligands. Dalton Trans 37:7701–7716

    Article  Google Scholar 

  • Yan X-L, Chen L-G, Zeng T (2006) 2,6-di-tert-butyl-4-(Phenyliminomethyl)phenol. Acta Crystallogr E62:o1455–o1456

    Google Scholar 

Download references

Acknowledgements

Grateful acknowledgement is made to the National Research Foundation, DST-NRF Centre of Excellence in Catalysis and Anglo Platinum Corporation for funding this project and the University of Cape Town for facilities.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Harry Chiririwa.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chiririwa, H., Aoyi, O. Synthesis and Characterization of New Tetradentate Ligands. Iran J Sci Technol Trans Sci 41, 1003–1009 (2017). https://doi.org/10.1007/s40995-017-0316-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40995-017-0316-8

Keywords

Navigation