Transition Metal Chemistry

, Volume 41, Issue 7, pp 775–781 | Cite as

Synthesis of a palladium(II) complex of a N-heterocylic carbene via transmetalation: crystal structure and antibacterial studies

  • Rosenani A. Haque
  • Umie F. M. Haziz
  • A. A. Amirul
  • Noor Shaheeda
  • Mohd R. Razali


An Ag(I)-N-heterocylic carbene (NHC) complex, [Ag(L)2]PF6 (L = 1-(2′-methylbenzyl)-3-(2″-propyl)benzimidazolium), was used as a transfer agent for the synthesis of a Pd(II)–NHC complex, formulated as [PdCl(L)2(MeCN)]PF6 (Pd1). The complex Pd1 was characterized by 1H and 13C NMR, FTIR spectroscopy and elemental analysis. Single crystal X-ray diffraction analysis reveals that the Pd(II) atom has a square planar geometry. This complex was screened for its antibacterial potential against the Gram-negative bacteria Escherichia coli (ATCC 25922) and the Gram-positive bacteria Staphylococcus aureus (ATCC 12600). These results are compared with those obtained for a standard antibiotic, ampicillin, and also the corresponding Ag(I)–NHC complex.

Supplementary material

11243_2016_78_MOESM1_ESM.doc (1.5 mb)
Supplementary material 1 (DOC 1559 kb)


  1. 1.
    Liu W, Gust R (2013) Chem Soc Rev 42:755CrossRefGoogle Scholar
  2. 2.
    Visbal R, Gimeno MC (2014) Chem Soc Rev 43:3551CrossRefGoogle Scholar
  3. 3.
    Oehninger L, Rubbiani R, Ott I (2013) Dalton Trans 42:3269CrossRefGoogle Scholar
  4. 4.
    Hemmert C, Gornitzka H (2016) Dalton Trans 45:440CrossRefGoogle Scholar
  5. 5.
    Budagumpi S, Haque RA, Endud S, Rehman GU, Salman AW (2013) Eur J Inorg Chem. doi:10.1002/ejic.201300483 Google Scholar
  6. 6.
    Garrison JC, Youngs WJ (2005) Chem Rev 105:3978CrossRefGoogle Scholar
  7. 7.
    Wanzlick HW, Schonherr HJ (1968) Angew Chem Int Ed Engl 7:141CrossRefGoogle Scholar
  8. 8.
    Öfele K (1968) J Organomet Chem 12:42CrossRefGoogle Scholar
  9. 9.
    Guerret O, Solé S, Gornitzka H, Teichert M, Trinquier G, Bertrand G (1997) J Am Chem Soc 119:6668CrossRefGoogle Scholar
  10. 10.
    Wang HWJ, Lin IJB (1998) Organometallics 17:972CrossRefGoogle Scholar
  11. 11.
    Tulloch AAD, Danopoulos AA, Winston S, Kleinhenz S, Eastham G (2000) J Chem Soc Dalton Trans. doi:10.1039/b007504n Google Scholar
  12. 12.
    Haque RA, Ghdhayeb MZ, Budagumpi S, Khadeer Ahamed AMB, Abdul Majid AMS (2013) Inorg Chim Acta 394:519CrossRefGoogle Scholar
  13. 13.
    Wylie WNO, Alan JL, Robert HM (2010) Organometallics 29:570CrossRefGoogle Scholar
  14. 14.
    Ai P, Gourlaouen C, Danopoulos AA, Braunstein P (2016) Inorg Chem 55:1219CrossRefGoogle Scholar
  15. 15.
    Huckaba AJ, Hollis TK, Howell TO, Valle HU, Wu Y (2013) Organometallics 32:63CrossRefGoogle Scholar
  16. 16.
    Lake BRM, Willans CE (2014) Organometallics 33:2027CrossRefGoogle Scholar
  17. 17.
    He Z, Zhang S-F, Xue J-R, Liang Y, Zhang X, Jing L-H, Qin D-B (2016) J Organomet Chem 808:12CrossRefGoogle Scholar
  18. 18.
    Iwasaki H, Teshima Y, Yamada Y, Ishikawa R, Koga Y, Matsubara K (2016) Dalton Trans 45:5713CrossRefGoogle Scholar
  19. 19.
    Arnold PL (2002) Heteroat Chem 13:538CrossRefGoogle Scholar
  20. 20.
    Herrmann WA, Schneider SK, Öfele K, Sakamoto M, Herdtweck E (2004) J Organomet Chem 689:2441CrossRefGoogle Scholar
  21. 21.
    Herrmann WA (2002) Angew Chem Int Ed 41:1290CrossRefGoogle Scholar
  22. 22.
    Roland S, Audouin M, Mangeney P (2004) Organometallics 23:3075CrossRefGoogle Scholar
  23. 23.
    Huynh HV, Han Y, Ho JHH, Tan GK (2006) Organometallics 25:3267CrossRefGoogle Scholar
  24. 24.
    Shen A, Ni C, Cao Y-C, Zhou H, Song G-H, Ye X-F (2014) Tetrahedron Lett 55:3278CrossRefGoogle Scholar
  25. 25.
    Lee J-Y, Lee J-Y, Chang Y-Y, Hu C-H, Wang NM, Lee HM (2015) Organometallics 34:4359CrossRefGoogle Scholar
  26. 26.
    Dahm G, Bailly C, Karmazin L, Bellemin-Laponnaz S (2015) J Organomet Chem 794:115CrossRefGoogle Scholar
  27. 27.
    McGuiness DS, Cavell KJ (2000) Organometallics 19:741CrossRefGoogle Scholar
  28. 28.
    Frøseth M, Dhindsa A, Røise H, Tilset M (2003) Dalton Trans. doi:10.1039/B308275J Google Scholar
  29. 29.
    Lee HM, Chiu PL, Hu C-H, Lai C-L, Chou Y-C (2005) J Organomet Chem 690:403CrossRefGoogle Scholar
  30. 30.
    Budagumpi S, Haque RA, Salman AW (2012) Coord Chem Rev 256:1787CrossRefGoogle Scholar
  31. 31.
    Wang C-H, Shih W-C, Chang HC, Kuo Y-Y, Hung W-C, Ong T-G, Li W-S (2011) J Med Chem 54:5245CrossRefGoogle Scholar
  32. 32.
    Dahm G, Bailly C, Karmazin L, Bellemin-Laponnaz S (2015) J Organomet Chem 794:115CrossRefGoogle Scholar
  33. 33.
    Matesanz AI, Albacete P, Souza P (2016) Polyhedron 109:161CrossRefGoogle Scholar
  34. 34.
    Zhu M, Cui X, Zhang S, Liu L, Han Z, Gao E (2016) J Inorg Biochem 157:34CrossRefGoogle Scholar
  35. 35.
    Ray S, Mohan R, Singh JK, Samantaray MK, Shaikh MM, Panda D, Ghosh P (2007) J Am Chem Soc 129:15042CrossRefGoogle Scholar
  36. 36.
    Haque RA, Salman AW, Budagumpi S, Abdullah AA-A, Abdul Majid AMS (2013) Metallomics 5:760CrossRefGoogle Scholar
  37. 37.
    Haque RA, Haziz UFM, Abdullah AA-A, Shaheeda N, Razali MR (2016) Polyhedron 109:208CrossRefGoogle Scholar
  38. 38.
    Sheldrick GM (2008) Acta Crystallogr Sect A 64:112CrossRefGoogle Scholar
  39. 39.
    Barbour LJ (2001) J Supramol Chem 1:189CrossRefGoogle Scholar
  40. 40.
    Drew WL, Barry AL, O’Toole R, Cherris JC (1972) Appl Microbiol 24:240Google Scholar
  41. 41.
    Nielsen DJ, Cavell KJ, Skelton BW, White AH (2002) Inorg Chim Acta 327:116CrossRefGoogle Scholar
  42. 42.
    Janiak C (2000) J Chem Soc Dalton Trans. doi:10.1039/B003010O Google Scholar
  43. 43.
    Razali MR, Urbatsch A, Deacon GB, Batten SR (2013) Polyhedron 64:352CrossRefGoogle Scholar
  44. 44.
    Razali MR, Chilton NF, Urbatsch A, Moubaraki B, Langley SK, Murray KS, Deacon GB, Batten SR (2013) Polyhedron 52:797CrossRefGoogle Scholar
  45. 45.
    Asekunowo PO, Haque RA, Razali MR, Budagumpi S (2015) Appl Organomet Chem 29:126CrossRefGoogle Scholar
  46. 46.
    Streciwilk W, Cassidy J, Hackenberg F, Müller-Bunz H, Paradisi F, Tacke M (2014) J Organomet Chem 749:88CrossRefGoogle Scholar
  47. 47.
    Haque RA, Asekunowo PO, Razali MR, Mohamad F (2014) Heteroat Chem 25:194CrossRefGoogle Scholar
  48. 48.
    Haque RA, Asekunowo PO, Razali MR (2014) Trans Met Chem 39:281CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  • Rosenani A. Haque
    • 1
  • Umie F. M. Haziz
    • 1
  • A. A. Amirul
    • 2
    • 3
  • Noor Shaheeda
    • 2
  • Mohd R. Razali
    • 1
  1. 1.School of Chemical SciencesUniversiti Sains Malaysia (USM)GelugorMalaysia
  2. 2.School of Biological SciencesUniversiti Sains Malaysia (USM)GelugorMalaysia
  3. 3.Centre of Chemical BiologyUniversiti Sains MalaysiaGelugorMalaysia

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