Skip to main content
Log in

Nickel(II), copper(II) and zinc(II) complexes with an N-pendent dimethyl derivative of an octamethyl macrocyclic ligand: synthesis, characterization and antimicrobial studies

  • Regular Article
  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

Interaction of CH3I with L (3,10-C-meso-Me8[14]diene) in the ratio of 4:1 in ethanolic solution at room temperature yielded N-pendent dimethyl derivative [(L-2H)(–CH3)2] denoted by LZ. Interaction of nickel(II) acetate tetrahydrate with LZ and subsequent addition of NaClO4·6H2O produced square planar orange-yellow product, [NiLZ](ClO4)2. The reaction of copper(II) perchlorate hexahydrate with LZ afforded four coordinated square planar red [CuLZ](ClO4)2. However, on the reaction of zinc(II) nitrate hexahydrate with LZ furnished white six coordinated two distereoisomeric complexes [ZnL(NO3)2] and [ZnL(NO3)2]. Axial addition reactions on four coordinated square planar [NiLZ](ClO4)2 with KX (X= SCN, NO3, Cl, Br or I) and NaNO2 resulted in six coordinated octahedral and square pyramidal axial addition products, such as [NiLZ(NCS)2], [NiLZ(NO3)(ClO4)], [NiLZCl(ClO4)], [NiLZBr2], [NiLZI2] and [NiLZ(NO2)](ClO4), respectively. However axial substitution reactions on [ZnL(NO3)2] with KY (Y= SCN, Cl or Br) and NaNO2 produced six coordinated octahedral axial substitution products [ZnL(NCS)2], [ZnLCl2], [ZnLBr2] and [ZnL(NO2)2]. Similarly, the axial substitution reactions on [ZnL(NO3)2] with KI and NaClO4.6H2O resulted in six coordinated octahedral axial substitution products [ZnLI2] and [ZnL(H2O)2](ClO4)2, respectively. The compounds have been characterized by analytical, spectroscopic, magnetochemical and conductivity data. The antimicrobial activities of the new ligand and its complexes have been tested against different micro pathogens.

Graphic abstract

Nickel(II), copper(II) and zinc(II) complexes with an N-pendent dimethyl derivative ligand LZ of an octamethyl tetraazmacrocyclic ligand were prepared. The compounds were characterized by different analytical and spectroscopic methods. Antibacterial and antifungal activities of these compounds against some bacteria and fungi were also investigated.

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
Str. 1
Str. 2
Str. 3
Str. 4
Str. 5
Str. 6
Str. 7

Similar content being viewed by others

References

  1. Hermann P, Kotek J, Kubíček V and Lukeš I 2008 Gadolinium(III) complexes as MRI contrast agents: ligand design and properties of the complexes Dalton Trans. 23 3027

  2. Bernhardt P V and Sharpe P C 2000 C-substituted macrocycles as candidates for radioimmunotherapy Inorg. Chem. 39 4123

    Article  CAS  Google Scholar 

  3. Biswas F B, Roy T G, Rahman M A and Emran T B 2014 An in vitro antibacterial and antifungal effects of cadmium(II) complexes of hexamethyltetraazacyclotetradecadiene ligands Asian Pac. J. Trop. Biomed. 7(sup 1) 534

    Article  Google Scholar 

  4. Roy T G, Hazari S K S, Dey B K, Miah H A, Olbrich F and Rehder D 2007 Syntheses and antimicrobial activities of isomers of N(4), N(11)-dimethyl-3,10-C-meso-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane and their nickel(II) complexes Inorg. Chem. 46 5372

    Article  CAS  Google Scholar 

  5. Parveez G and Athar A H 2015 Biological activity studies on metal complexes of macrocyclic Schiff base ligand: synthesis and spectroscopic characterization J. Braz. Chem. Soc. 26 1331

    Google Scholar 

  6. Gull P, Dar O A, Malik M A and Hashmi A A 2016 Design, synthesis, characterization and antimicrobial/antioxidant activities of 1, 4-dicarbonyl-phenyl dihydrazide based macrocyclic ligand and its Cu(II), Co(II) and Ni(II) complexes Microb. Pathog. 100 237

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

  8. Rzuezek S G, Pilch D S, Liu A, Liu L, LaVoie E J and Rice J E 2010 Macrocyclic pyridyl polyoxazoles: selective RNA and DNA G-quadruplex ligands as antitumor agents J. Med. Chem. 53 3632

    Article  Google Scholar 

  9. Shankarwar S G, Nagolkar B B, Shelke V A and Chondhekar T K 2015 Synthesis, spectral, thermal and antimicrobial studies of transition metal complexes of 14-membered tetraaza[N4] macrocyclic ligand Spectrochim. Acta A 145 188

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. Singh A K, Panwar A, Kumar S and Baniwal S 1999 Chromium(III)-selective electrode based on a macrocyclic compound Analyst 124 521

  12. Roy T G, Hazari S K S, Meah H A, Gupta S K D, Roy P G, Behrens U and Rehder D 2014 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

  13. Roy T G, Hazari S K S, Dey B K, Meah H A, Bader C and Rehder D 2004 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

  14. Rabi S, Mia H A, Hazari S K S, Roy T G and Manchur M A 2018 Nickel(II) complexes with N-pendent macrocyclic ligands: synthesis, characterization and antimicrobial activities Int. J. Int. Sci. Technol. 3 75

    Google Scholar 

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

    Article  CAS  Google Scholar 

  16. Roy T G, Hazari S K S, Dey B K, Miah H A and Tiekink E R T 2001 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

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

  18. Bembi R, Roy T G, Jhanji A K and Mahewari 1990 A Polyazamacrocycles. Part 7 Kinetics of aquation of trans-dichloro and trans-chloro(nitro) complexes of cobalt(III) with tera-aza macrocycles J. Chem. Soc. Dalton Trans. 11 3531

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

    Article  CAS  Google Scholar 

  20. Roy T G, Hazari S K S, Dey B K, Meah H A, Rahman M S, Kim D I and Park Y C 2007 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

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  22. Nakamotto K 1963 Infrared Spectra of Inorganic and Coordination Compounds Second edn. (New York: John Wiley & Sons) p. 187

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

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  26. Sabatini A and Bertin I 1965 Infrared Spectra between 100 and 2500 cm−1 of some complex metal cyanates, thiocyanates and selenocyanates Inorg. Chem. 4 959

    Article  CAS  Google Scholar 

  27. Conley R T 1966 Infrared Spectroscopy (Boston, Massachusetts: Allyn and Bacon)

  28. Geary W J 1971 The use of conductivity measurements in organic solvents for the characterization of coordination compounds Coord. Chem. Rev. 7 81

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  31. Roy T G, Hazari S K S, Dey B K, Chakraborty S and Tiekink E R T 1999 Synthesis, characterisation and antifungal activities of some new copper(II) complexes of octamethyl tetraazacyclotetradecadiene Met. Based Drugs 6 345

  32. Mochizuki K and Kondo 1995 Isolation and Vis-Absorption Spectrum of trans [Ni(OH2)2(cyclam)]Cl2.cntdot.4H2OT Inorg. Chem. 34 6241

  33. Chandra S and Krishan S K 1983 Synthesis and characterization of copper(II) complexes of a macrocyclic Ligand Trans. Met. Chem. 8 1

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

    Article  CAS  Google Scholar 

  35. Jorgensen J H and Ferrar M J 2009 Antimicrobial susceptibility testing: a review of general principles and contemporary practices Clin. Infect. Dis. 49 1749

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Acknowledgement

We gratefully acknowledge the Ministry of Science and Technology, People’s Republic of Bangladesh, for awarding a Research Grant to Professor Dr. Tapashi Ghosh Roy and Professor Benu Kumar Dey, Department of Chemistry, University of Chittagong, Bangladesh.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Tapashi Ghosh Roy.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 2324 kb)

Supplementary Information (SI)

Supplementary Information (SI)

The synthesis of N-pendent ligand LZ has been shown in Scheme S1 (Supplementary Information). IR spectra, mass spectra & fragmentation pattern, 1H-NMR and 13C-NMR spectra for the newly synthesized N-pendent ligand LZ have been included in, Figure-S1, Figure S2 & Table S1, Figure S3 and Figure S4, respectively. However, some representative IR spectra of metal complexes of LZ have been shown in Figure S5 to Figure S11. On the other hand 1H-NMR spectra for [NiLZ](ClO4)2, [ZnL(NO3)2], [ZnL(NO3)2], [ZnL(NO2)2] and [ZnLBr2] have been added as Figure S12, Figure S13, Figure S14, Figure S15 and Figure S16, respectively. Some UV spectra of Ni(II) and Cu(II) complexes of N-pendent ligand LZ have been included in Figure S17. The nickel(II), copper(II) and zinc(II) complexes have been shown by Str. S1 to Str. S7. The results on antifungal and antibacterial activities of the new compounds have been included in Table S2 and Table S3 & Table S4, respectively. Supplementary Information is available at www.ias.ac.in/chemsci.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Das Gupta, S.K., Rabi, S., Ghosh, D. et al. Nickel(II), copper(II) and zinc(II) complexes with an N-pendent dimethyl derivative of an octamethyl macrocyclic ligand: synthesis, characterization and antimicrobial studies. J Chem Sci 133, 7 (2021). https://doi.org/10.1007/s12039-020-01861-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s12039-020-01861-7

Keywords

Navigation