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Synthesis, characterization and antibacterial activities of nickel(II) and copper(II) complexes of an N-pendent cyanoethyl derivative of a tetraazamacrocycle

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Abstract

An octamethyl substituted tetraazacylotetradecadiene ligand salt Me8[14]diene.2HClO4 (L.2HClO4) on reduction produced three isomeric C-chiral ligands LA, LB & LC. Interaction of LB with excess acrylonitrile resulted in a N-pendent cyanoethyl derivative ligand, LBX. Reaction of LBX with nickel(II) salt, Ni(CH3COO)2.4H2O followed by the addition of NaClO4 afforded the complex, [NiLB](ClO4)2, as resulted by the interaction with LB instead of LBX with the same nickel(II) salt which on twelve hours reflux with acrylonitrile yielded square planar nickel(II) diperchlorate complex, [NiLBX](ClO4)2, This complex underwent axial addition reactions with KX (X = SCN, Br or I) and NaNO2 to form octahedral diisothiocyanatonickel(II) complex, [NiLBX(NCS)2]; dibromidonickel(II) complex, [NiLBXBr2]; diiodidonickel(II) complex, [NiLBXI2] and monoaquamononitronickel(II) perchlorate complex, [NiLBX(NO2)(H2O)](ClO4) respectively. The ligand, LBX with copper(II) chloride yielded purple dichloridocopper(II) complex, [CuLBXCl2] of octahedral geometry which underwent axial substitution reactions with KX and NaNO2 to form octahedral diisothiocyanatocopper(II) complex [CuLBX(NCS)2]; dibromidocopper(II) complex [CuLBXBr2]; diiodidocopper(II) complex, [CuLBXI2] and dinitrocopper(II) complex [CuLBX(NO2)2] respectively. These complexes were characterized on the basis of elemental, spectroscopic, magnetochemical and conductrometric analysis. The antibacterial activities of the ligand and complexes have been investigated against different human pathogenic gram positive and gram negative bacteria.

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References

  1. Ilhan, S., Temel, H.: Synthesis and characterization of a new macrocyclic Schiff base derived from 2,6-diaminopyradine and 1,10-bis(2-formlphenyl)-1,4,7,10-tetraoxadecane and its Cu(II), Ni(II), Pb(II), Co(II) and La(III) complexes. Trans. Met. Chem. 32, 1039–1046 (2007)

    CAS  Google Scholar 

  2. Lindoy, L.F.: The chemistry of macrocyclic ligand complexes. Cambridge University Press, Cambridge (1989)

    Google Scholar 

  3. Kosmas, C., Snook, D., Gooden, C.S., Courtenay Luck, N.S., McCall, M.J., Meares, C.F., Epenetos, A.A.: Development of humoral immune responses against a macrocyclic chelating agent (DOTA) in cancer patients receiving radioimmunoconjugates for imaging and therapy. Cancer Res. 52, 904–911 (1992)

    CAS  PubMed  Google Scholar 

  4. Demirbilek, M., Pişkin, E.: Effects of copper-cyclam and copper-cyclam/polymer complexes on HeLa cells. J. Biol. Chem. 36, 263–271 (2008)

    Google Scholar 

  5. Matsubara, T., Hirao, K.: Density functional study of the binding of the cyclen coordinated M(II) (M=Zn, Cu, Ni) complexes to the DNA base. Why is Zn better to bind? J. Mol. Struct. Theochem. 581, 203–213 (2002)

    CAS  Google Scholar 

  6. Shankarwar, S.G., Nagolkar, B.B., Shelke, V.A., Chondhekar, T.K.: Synthesis, spectral, thermal and antimicrobial studies of transition metal complexes of 14-membered tetraaza[N4] macrocyclic ligand. Spectrochim. Acta A Mol. Biomol. Spectrosc. 145, 188–193 (2015)

    CAS  PubMed  Google Scholar 

  7. El-Boraey, H.A., El-Gammal, O.A.: New 15-membered tetraaza (N4) macrocyclic ligand and its transition metal complexes: spectral, magnetic, thermal and anticancer activity. Spectrochim. Acta A Mol. Biomol. Spectrosc. 138, 553–562 (2015)

    CAS  PubMed  Google Scholar 

  8. Suh, M.P., Moon, H.R., Lee, E.Y., Jang, S.Y.: A redox-active two-dimensional coordination polymer: preparation of silver and gold nanoparticles and crystal dynamics on guest removal. J. Am. Chem. Soc. 128, 4710–4718 (2006)

    CAS  PubMed  Google Scholar 

  9. Hyun-soon, C., Kayhan, G., Dangshe, M., Diane, E.M., Terrish, O., Martin, W.B.: Synthesis and biological evaluation of novel macrocyclic ligands with pendent donor groups as potential yttrium chelators for radioimmunotherapy with improved complex formation kinetics. J. Med. Chem. 45, 3458–3464 (2002)

    Google Scholar 

  10. Curtis, N.F., Swann, S.A., Waters, T.N., Maxwell, I.E.: Isomerism of some octamethyl-1,5,8,12- tetraazacyclotetradecadiene complexes of nickel(II) and copper(II). J. Am. Chem. Soc. 91, 4588–4589 (1969)

    CAS  Google Scholar 

  11. Bembi, R., Sondhi, S.M., Singh, A.K., Jhanjii, A.K., Roy, T.G., Lown, J.W., Ball, R.G.: Polyazamacrocycles V. Structure of isomeric 3,5,7,7,10,12,14,14-octamethyl- 1,4,8,11tetraazacyclotetradecanes. Bull. Chem. Soc. Jpn. 62, 3701–3705 (1989)

    CAS  Google Scholar 

  12. Roy, T.G., Hazari, S.K.S., Dey, B.K., Miah, H.A., Tiekink, E.R.T.: Trans-(3S,5S,10R,12R)-1,8-bis(2-cyanoethyl)-C-meso-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane. Acta Cryst. E57, 0524–0525 (2001)

    Google Scholar 

  13. Alam, M.S., Rabi, S., Rahman, M.M., Baidya, A., Debi, M., Roy, T.G.: Synthesis, characterization and antimicrobial studies of cadmium(II) complexes with a tetraazamacrocycle (LB) and its cyanoethyl N-pendent derivative (LBX). J. Chem. Sci. 130(35), 1–10 (2018)

    CAS  Google Scholar 

  14. Bembi, R., Roy, T.G., Jhanji, A.K., Mahewari, A.: Polyazamacrocycles. Part 7 Kinetics of aquation of trans-dichloro and trans-chloro(nitro) complexes of cobalt(III) with teraaza macrocycles. J. Chem. Soc. Dalton Trans. (1990). https://doi.org/10.1039/DT9900003531

    Article  Google Scholar 

  15. Roy, T.G., Bembi, R., Hazari, S.K.S., Dey, B.K., Acharjee, T.K., Horn, E., Tiekink, E.R.T.: Characterization of diastereoisomeric [Ni(Me8[14]ane)]2+ cations. J. Coord. Chem. 55, 853–862 (2002)

    CAS  Google Scholar 

  16. Roy, T.G., Hazari, S.K.S., Dey, B.K., Meah, H.A., Rahman, M.S., Kim, D.I., Park, Y.C.: Synthesis, electrolytic behavior and antimicrobial activities of cadmium complexes of isomers of 3,10-C-meso-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane. J. Coord. Chem. 40, 1567–1578 (2007)

    Google Scholar 

  17. Roy, T.G., Hazari, S.K.S., Dey, B.K., Chakrabarty, S., Tiekink, E.R.T.: Synthesis, characterization and antifungal activities of some new copper(II) complexes of octamethyl tetraazacyclotetradecadiene. Metal Based Drugs. 6(6), 345–354 (1999)

    CAS  PubMed  PubMed Central  Google Scholar 

  18. Roy, T.G., Hazari, S.K.S., Nath, R.K., Nath, B.C., Manchur, A.: Synthesis and antimicrobial activities of some cadmium(II) and zinc(II) complexes of 3, 10- C- meso- 3, 5, 7, 7, 10, 12, 14, 14- octamethyl—1, 4, 8, 11—tetraazacyclotetradecadiene (L1)”. J. Bangladesh Chem. Soc. 22(2), 111–122 (2009)

    CAS  Google Scholar 

  19. Roy, T.G., Hazari, S.K.S., Meah, H.A., Gupta, S.K.D., Roy, P.G., Behrens, U., Rehder, D.: Synthesis and antimicrobial activities of copper(II) complexes of N(4), N(11)-dimethyl (LBZ & LCZ) and N(4)-monomethyl(LCZ1(-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane. Crystal and molecular structure of [CuLCZ1](ClO4)2. Inorg. Chim. Acta 415, 124–131 (2014)

    CAS  Google Scholar 

  20. Roy, T.G., Hazari, S.K.S., Dey, B.K., Meah, H.A., Bader, C., Rehder, D.: Copper(II) and nickel(II) complexes of N, N-bis(2-hydroxyethyl)-octamethyl-1,4,8,11-tetraaza-cyclotetradecane. Eur. J. Inorg. Chem. 2004, 4115–4123 (2004)

    Google Scholar 

  21. Geary, W.J.: The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord. Chem. Rev. 7(1), 81–122 (1971)

    CAS  Google Scholar 

  22. Al-Obaidi, O.H.S., Al-Hiti, A.R.H.: Synthesis, spectral and theoretical studies of macrocyclic Cu(II), Ni(II) and Co(II) complexes by template reaction of malonic acid with metal (II) chloride and urea or thiourea. Am. Chem. Sci. J. 2(1), 1–11 (2012)

    CAS  Google Scholar 

  23. Farago, M.E., James, J.M.: Coordination of thiocyanate and selenocyanate in some diamine complexes of nickel(II) and copper(II). Inorg. Chem. 4, 1706–1711 (1965)

    CAS  Google Scholar 

  24. Sabatini, A., Bertin, I.: Infrared Spectra between 100 and 2500 cm-1 of some complex metal cyanates, thiocyanates, and selenocyanates. Inorg. Chem. 4, 959–961 (1965)

    CAS  Google Scholar 

  25. Bembi, R., Drew, M.G.B., Singh, R., Roy, T.G.: Polyazamacrocycles. 9. Characterisation of diastereoisomeric trans-(Co(Me8[14]ane)Cl2]+ complexes. Inorg. Chem. 30, 1403–1406 (1991)

    CAS  Google Scholar 

  26. Nakagawa, I., Shimanouchi, T., Yamasaki, K.: Infrared spectra and force constants of ammine complexes. Inorg. Chem. 3(12), 1805–1806 (1964)

    Google Scholar 

  27. Le, P.M., Mathieu, J.P.P.: Spectres de vibration et structure de composés de coordination nitrés. J. Chim. Phys. 60, 1319–1333 (1963)

    Google Scholar 

  28. Cleare, M.J., Griffith, W.P.: Infrared spectra of isotopically substituted nitro-, nitrito-, and nitrosyl complexes. J. Chem. Soc. A (1967). https://doi.org/10.1039/J19670001144

    Article  Google Scholar 

  29. Bembi, R., Bhardwaj, V.K., Singh, R., Teneja, K., Aftab, S.: Synthesis and characterization of copper(II), nickel(II) and cobalt(III) complexes with 1,4,8,11-tetraazacyclohexadecane and 1,4,8,11-tetraazacyclopheptadecane. Inorg. Chem. 23, 4153–4157 (1984)

    CAS  Google Scholar 

  30. Martrin, L.Y., Sperati, C.R., Busch, D.H.J.: The spectrochemical properties of tetragonal complexes of high spin nickel(II) containing macrocyclic ligands. Chem. Soc. 99, 2968–2981 (1977)

    Google Scholar 

  31. Nolan, M.J., James, D.W.: Vibrational spectra of metal-nitro I. The hexanitroplatinate anion. Aust. J. Chem. 23, 1043–1047 (1970)

    CAS  Google Scholar 

  32. Huneka, J.T., Meisner, B., Walford, L., Bain, R.L.: Infrared and Raman spectra of Isotopically substituted tetranitrriplatinate(II) salts. Spectrosc. Lett. 7, 91–96 (1974)

    Google Scholar 

  33. James, D.W., Nolan, M.J.: Vibrational spectra of metal nitro III. The tetranitroplatinate and paladate(II) ion. Aust. J. Chem. 26, 1433 (1973)

    CAS  Google Scholar 

  34. Roy, T.G., Hazari, S.K.S., Dey, B.K., Dutta, S., Monsur, M.A., Tiekink, E.R.T.: Axial addition in diastereoisomeric [Cu(Me8[14]ane)](ClO4)2] complexes: anti-fungal and anti- bacterial activities. J. Coord. Chem. 59(15), 1757–1767 (2006)

    CAS  Google Scholar 

  35. Nakamoto, K.: Infrared spectra of inorganic and coordination compounds, 2nd edn. Wiley, New York (1963)

    Google Scholar 

  36. Roy, T.G., Hazari, S.K.S., Dey, B.K., Nath, B.C., Dutta, A., Olbrich, F., Rehder, D.: Syntheses, electrolytic behaviour and antifungal activities of Zn(II) complexes of isomers of 3,10-C-meso-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane (L). Crystal and molecular structure of [ZnLB(NO3)]NO3 (LB = a, e, a, e-L). Inorg. Chim. Acta 371, 63–70 (2011)

    CAS  Google Scholar 

  37. Chandra, S., Krishan, S.K.: Synthesis and characterization of copper(ii) complexes of a macrocyclic ligand. Trans. Met. Chem. 8, 1–3 (1983)

    CAS  Google Scholar 

  38. Chandra, S., Tyagi, M., Agrawal, S.: Synthesis and characterization of a tetraaza macrocyclic ligand and its cobalt(II), nickel(II) and copper(II) complexes. J. Serb. Chem. Soc. 75(7), 935–941 (2010)

    CAS  Google Scholar 

  39. Priya, N.P., Arunachalam, S., Manimaran, A., Muthupriya, D., Jayabalakrishnan, C.: Mononuclear Ru(III) Schiff base complexes: synthesis, spectral, redox, catalytic and biological activity studies. Spectrochim. Acta Part A 72(3), 670–676 (2008)

    Google Scholar 

  40. Lallan, M., Kumar, S.V.: Synthesis, structural and antifungal studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with new Schiff bases bearing benzimidazoles. Indian J. Chem. 32A, 446–449 (1993)

    Google Scholar 

  41. Malhotra, R., Kumar, S., Dhindsa, K.S.: Synthesis, characterization and antimicrobial activity of cobalt(II), nickel(II), copper(II) and zinc(II) complexes of acryloxyacetic acid hydrazides. Indian J. Chem. 32A, 457–459 (1993)

    CAS  Google Scholar 

  42. Salehi, M., Hasanzadeh, M.: Characterization, crystal structures, electrochemical and antibacterial studies of four new binuclear cobalt(III) complexes derived from o-aminobenzyl alcohol. Inorg. Chim. Acta 426, 6–14 (2015)

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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Acknowledgement

The authors would like to extend their sincere appreciation to the University Grants Commission, Bangladesh, to give a research grant to Professor Dr. Tapashi Ghosh Roy, Department of Chemistry, University of Chittagong, Chittagong-4331, Bangladesh.

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Authors and Affiliations

  1. Department of Chemistry, Chittagong University of Engineering & Technology, Chattogram, 4349, Bangladesh

    Ratul Kumar Shil & Saswata Rabi

  2. Department of Chemistry, University of Chittagong, Chattogram, 4331, Bangladesh

    Shawon Barua, Ruhul Amin & Tapashi Ghosh Roy

  3. Department of Microbiology, University of Chittagong, Chattogram, 4331, Bangladesh

    Md. Abul Manchur

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  1. Ratul Kumar Shil
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Shil, R.K., Rabi, S., Barua, S. et al. Synthesis, characterization and antibacterial activities of nickel(II) and copper(II) complexes of an N-pendent cyanoethyl derivative of a tetraazamacrocycle. J Incl Phenom Macrocycl Chem 99, 87–98 (2021). https://doi.org/10.1007/s10847-020-01031-9

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