Journal of Thermal Analysis and Calorimetry

, Volume 112, Issue 2, pp 671–681 | Cite as

Synthesis, thermal characterization, and antimicrobial activity of lanthanum, cerium, and thorium complexes of amino acid Schiff base ligand

  • Samir Alghool
  • Hanan F. Abd El-Halim
  • M. S. Abd El-sadek
  • I. S. Yahia
  • L. A. Wahab
Article

Abstract

Metal complexes of La(III), Ce(IV), and Th(IV), with the amino Schiff base ligand, [N-(2-hydroxybenzyl)-l-methionine acid](H3L), were prepared in the presence of triethylamine as a deprotonating agent. All synthesized compounds were identified and confirmed by mass spectra, elemental analyses, molar conductivities, and spectral analyses (UV–Visible, IR, 1H NMR, and 13CNMR). Conductance measurements suggest the non-electrolytic nature and the complexes were isolated in 1:1 ratios. The thermal decomposition of the complexes was discussed in relation to structure. The data from thermogravimetric analysis clearly indicated that the decomposition of the complexes proceeds in four or five steps and the organic part of the complexes decomposed in one or two intermediates. The decomposition of all complexes ended with metal oxide and carbon residue. The Schiff bases and their complexes were screened for their antibacterial (Escherichia coli, Staphylococcus aureus) and antifungal (Aspergillus flavus and Candida Albicans) activities.

Keywords

Amino acid Thermal studies Schiff base Metal complexes Bacterial 

References

  1. 1.
    Pravat B, Jonathan P, Andrew RT, Alexandra MZS. First synthesis of a unique dilead Schiff base complex. J Chem Soc Dalton Trans. 1998;(19):3149–50.Google Scholar
  2. 2.
    Neelakantan MA, Esakkiammal M, Mariappan SS, Dharmaraja J, Jeyakumar T. Synthesis, characterization and biocidal activities of some Schiff base metal complexes. Indian J Pharm Sci. 2010;72(2):216–22.CrossRefGoogle Scholar
  3. 3.
    Lin SY, Tseng JM, Lee MK. Thermal runaway evaluation of α-methylstyrene and trans-β-methylstyrene with benzaldehyde. J Therm Anal Calorim. 2009;95(3):559–63.CrossRefGoogle Scholar
  4. 4.
    Omid P, Anne-Christine C, Christoph J, Hassan HM. Hydrazone Schiff base-manganese(II) complexes: synthesis, crystal structure and catalytic reactivity. Inorg Chim Acta. 2007;360(5):1599–608.CrossRefGoogle Scholar
  5. 5.
    Wei QY, Xiong JJ, Jiang H, Zhang C, Wen Ye. The antimicrobial activities of the cinnamaldehyde adducts with amino acids. Int J Food Microbiol. 2011;150(2–3):164–70.CrossRefGoogle Scholar
  6. 6.
    Yinjian Z, Ming Z, Yingting W, Chunyu L, Jianhui W, Meiqing Z, Li P, Shiqi P. Synthesis and in vitro cytotoxicity of aminocoumarin platinum(II) complexes. Bioorg Med Chem. 2010;18(6):2165–72.CrossRefGoogle Scholar
  7. 7.
    Nahid N, Sumaiya H, Tansir A, Asma P. Synthesis, characterization, and biological evaluation of new polyester containing Schiff base metal complexes. J Therm Anal Calorim. 2011;105(3):969–79.CrossRefGoogle Scholar
  8. 8.
    Gloria CF, Peter JN, Harry AD. Heme biosynthesis in mammalian systems: evidence of a Schiff base linkage between the pyridoxal 5′-phosphate cofactor and a lysine residue in 5-aminolevulinate synthase. Protein Sci. 1993;2(11):1959–65.CrossRefGoogle Scholar
  9. 9.
    Xiao FM, Dong DL, Jin LT, Ying YK, Shi PY. DNA binding and cleavage activity of reduced amino-acid Schiff base complexes of cobalt(II), copper(II), and cadmium(II). Transit Met Chem. 2009;34(5):475–81.CrossRefGoogle Scholar
  10. 10.
    Nikhil UN, Carl AD, Huimin Z. Engineering of enzymes for selective catalysis. Curr Org Chem. 2010;14(17):1870–82.CrossRefGoogle Scholar
  11. 11.
    Ando R, Inden H, Sugino M, Ono H, Sakaeda D, Yagyu T, Maeda M. Spectroscopic characterization of amino acid and amino acid ester–Schiff-base complexes of oxovanadium and their catalysis in sulfide oxidation. Inorg Chim Acta. 2004;357(5):1337–44.CrossRefGoogle Scholar
  12. 12.
    Kulkarni A, Patil SA, Badami PS. Synthesis, characterization, DNA cleavage and in vitro antimicrobial studies of La(III), Th(IV) and VO(IV) complexes with Schiff bases of coumarin derivatives. Eur J Med Chem. 2009;44(7):2904–12.CrossRefGoogle Scholar
  13. 13.
    Leovac VM, Szécsényi KM, Ješić SV, Ćešljević VI, Markov S, Wadsten T. Metal complexes with girard reagents-based ligands. J Therm Anal Calorim. 2006;86(2):379–84.CrossRefGoogle Scholar
  14. 14.
    Haiduc I, Silvestru C. Metal compounds in cancer chemotherapy. Coord Chem Rev. 1990;99:253–6.CrossRefGoogle Scholar
  15. 15.
    Guo YL, Dou W, Wang YW, Liu WS, Wang DQ. Preparation, luminescent properties of N-phenyl-2-{2′-[(phenyl-ethyl-carbamoyl)-methoxy]-biphenyl-2-yloxy}-N-ethyl-acetamide (L) lanthanide complexes and the supramolecular structures of [La(pic)3L] and 2[La(NO3)3L(H2O)] H2O 0.5C2H5OH. Polyhedron. 2007;26(8):1699–710.CrossRefGoogle Scholar
  16. 16.
    Minhus Q, Huifang S, Xiaoping JCQ. Polymerization of dimethylaminoethyl methacrylate catalyzed by substituted indenyl lanthanide(II) complexes. J Rare Earths. 2007;25(6):721–4.CrossRefGoogle Scholar
  17. 17.
    Gfirkan P, Nuren S. Potentiometric determination of stability constants of lanthanon(III) complexes with some Schiff bases and benzothiazolines. Talanta. 1997;44(11):1935–40.CrossRefGoogle Scholar
  18. 18.
    Zhi-Yong W, Duan-Jun X, Zi-Xian F. Synthesis and catalytic properties of a Ni(II) complex with tetraglycol aldehyde bis(methionine) Schiff base. Polyhedron. 2001;20(3–4):281–4.Google Scholar
  19. 19.
    Meizhu R, Chong L, Jinyu H, Wenbo S, Yufei Z, Hua W. Catalytic oxidation of alcohols by a novel copper Schiff base ligand derived from acetylacetonate and l-leucine in ionic liquids. Catal Lett. 2008;125(1–2):52–6.Google Scholar
  20. 20.
    Renata Ł. Hydrothermal synthesis, thermal and luminescent investigations of lanthanide(III) coordination polymers based on the 4,4′-oxybis(benzoate) ligand. J Therm Anal Calorim. 2012;108(3):1101–10.CrossRefGoogle Scholar
  21. 21.
    Gupta R, Saxena RK, Chatarvedi P, Virdi JS. Chitinase production by Streptomyces viridificans: its potential in fungal cell wall lysis. J Appl Bacteriol. 1995;78(4):378–83.CrossRefGoogle Scholar
  22. 22.
    Alam MA, Koner RR, Das A, Nethaji M, Ray M. Rationalizing the effects of amino acid side chain, pyridine, and imidazole on the assembly and reversible disassembly of a octanuclear Cu(II) complex. Cryst Growth Des. 2007;7(9):1818–24.CrossRefGoogle Scholar
  23. 23.
    Hoye TR, Hanson PR, Vyvyan JR. l guide to first-order multiplet analysis in lH NMR spectroscopy. J Org Chem. 1994;59(15):4096–103.CrossRefGoogle Scholar
  24. 24.
    Alghool S. Metal complexes of azo coumarin derivative: synthesis, spectroscopic, thermal, and antimicrobial studies. J Coord Chem. 2010;63(18):3322–33.CrossRefGoogle Scholar
  25. 25.
    Zhang X, Zhang Y, Yang Y, China PR, Yange R, Jin D, Ynth S. Synthesis and characterization of glycine Schiff base complexes of the light lanthanide elements. React Inorg Met Org Chem. 2000;30(1):45–55.CrossRefGoogle Scholar
  26. 26.
    Soliman AA. Spectral and thermal study of the ternary complexes of nickel with sulfasalazine and some amino acids. Spectrochim Acta Part A. 2006;65(5):1180–6.CrossRefGoogle Scholar
  27. 27.
    Mohanan K, Thankamony M, Kumari BS. Synthesis, spectroscopic characterization, and thermal decomposition kinetics of some lanthanide(III) nitrate complexes of 2-(N-o-hydroxyacetophenone)amino-3-carboxyethyl-4, 5, 6, 7-tetrahydrobenzo[b]thiophene. J Rare Earths. 2008;26(4):463–8.CrossRefGoogle Scholar

Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2012

Authors and Affiliations

  • Samir Alghool
    • 1
  • Hanan F. Abd El-Halim
    • 2
  • M. S. Abd El-sadek
    • 3
  • I. S. Yahia
    • 4
  • L. A. Wahab
    • 5
  1. 1.Department of Chemistry, Faculty of SciencePort Said UniversityPort SaidEgypt
  2. 2.Department of Chemistry, Faculty of Pharmacy-PharmaceuticalMisr International UniversityCairoEgypt
  3. 3.Physics Department, Faculty of ScienceSouth Valley UniversityQenaEgypt
  4. 4.Physics Department, Faculty of EducationAin Shams UniversityRoxy, CairoEgypt
  5. 5.Physics DepartmentNational Center for Radiation Research and TechnologyNaser City, CairoEgypt

Personalised recommendations