SYNTHESIS, CHARACTERIZATION AND ELECTROCHEMICAL INVESTIGATION OF NOVEL 17-MEMBERED DIOXADIAZA NAPTHALDEHYDE BASED MACROCYCLIC LIGAND AND ITS COMPLEXES OF Co (III), Ni (II) AND Cu (II) PERCHLORATE IONS

Authors

  • A. N. Paul Angelo Research Scholar, Department of Chemistry, St. Joseph's College (Autonomous), Tiruchirappalli 620002
  • L. Rakesh Sharma St. Joseph's College (Autonomous)
  • K. N. Sabharwal Indira Gandhi Centre for Atomic Research

Keywords:

The synthesis and characterization of dioxadiaza macrocyclic ligand and its complexes of Co(III), Ni(II) and Cu(II) perchlorate complexes

Abstract

Objective: The objective of this research is to synthesis hitherto, novel unreported [17]-membered dioxadiaza napthaldehyde based macrocyclic ligand (L) and to synthesize its Co(III), Ni(II) and Cu(II) metal ion complexes.

Methods: The synthesis of the ligand has been accomplished by two different synthetic routes each involving two stages. 2-Hydroxy-1-Napthaldehyde in the presence of potassium carbonate was treated with α,α'-dibromo-m-xylene to yield the dial derivative (I). The dial derivative (I) was further made to undergo Schiff base condensation with 1,2-diaminobenzene to yield the bright yellow macrocycle (L) in good yield. In the second method the Schiff base condensed product Napthaloph was synthesized and allowed to undergo Williamson's condensation with α,α'-dibromo-m-xylene to yield the ligand (L).

Results: The ligand and its complexes were characterized by elemental analysis, electronic spectroscopy, IR, Conductivity measurements, EPR, magnetic susceptibility, 1H NMR and MS. The neutral seventeen membered tetradentate dioxadiaza ligand (L) readily complexes with Co(III), Ni(II) and Cu(II) perchlorate salts in 1:1 mole ratio to yield complexes of formulae [Co(L)X2]ClO4, [Ni(L)X2], [Cu(L)X]ClO4, (X = Cl-, Br-and NO3-). The complexes were also synthesized by the metal template method. The yield of the template procedure was found to be greater than the non-template method.

Conclusion: A hitherto 2, 10-dioxa-21,29-diaza-heptacyclo-[29.4.2.1[4,8].0[1,32].0[11,20].0[14,19].0[23,28].0[32,37]]-tetraconta-4, 6, 8, 11, 13, 15, 17, 19, 21, 23, 25, 27, 29, 31, 33, 35, 37, 39-octatecaene. The [17]-membered tetradentate dioxadiaza macrocycle (L) was found to accommodate Co3+, Ni2+, and Cu2+ions with ease due to the presence of flexible alkyl groups. Further studies with the inner-transition metal ions will be highly informative in understanding the coordinating capabilities of lanthanides and actinides.

 

Downloads

Download data is not yet available.

References

Anil Kumar MR, Shanmukhappa S, Rangaswamy BE, Revansiddappa M. Synthesis and characterization of copper(II) complexes with Schiff bases of 2-hydroxy-1-naphyhaldehyde. Int J Innovative Res Sci Eng Technol 2015;4:1175-87.

Uddin MN, Chowdhury DA, Rony Md M. Complexes of Schiff bases derived from 2-hydroxyaldehyde and propane-1,2-diamine: Synthesis, characterization and antibacterial screening. Am J Chem Appl 2014;1:12-8.

Dhamnaskar RS. Green, eco-friendly synthesis and characterization of copper(II) complexes with Schiff bases of 2-hydroxy-1-naphyhaldehyde. Golden Res Thoughts 2015;4:1-7.

Chandra S, Gupta LK, Agarawal S. Metal ion prompted macrocyclic complexes derived from indole-2,3-dione (Isatin) and orthophenylenediamine with their spectroscopic and antibacterial studies. Trans Met Chem 2007;32:240-5.

Hanafy AI, Maki ABKT, Mostafa MM. Metal ion prompted macrocyclic complexes derived from indole-2,3-dione (Isatin) and orthophenylenediamine with their spectroscopic and antibacterial studies. Trans Met Chem 2007;32:960-6.

Mishra AK, Panwar P, Chopra M, Sharma RK, Chatal J. Synthesis and characterization of copper(II) complexes with Schiff bases of 2-hydroxy-1-naphyhaldehyde. New J Chem 2003;27:1054.

Maneiro M, Bermejo MR, Fernandez MI, Gomez-Forneas E, Gonzalez-Noya M. Tyryshkin synthesis and characterization of copper(II) complexes with Schiff bases of 2-hydroxy-1-naphyhaldehyd. New J Chem 2003;27:727.

Mhaske G, Nilkanth P, Auti A, Davange S, Shelke S. Complexes of Schiff bases derived from 2-hydroxyaldehyde and propane-1,2-diamine: Synthesis, characterization and antibacterial Screening. Int J Innovative Res Sci Eng Technol 2014;3:8156-64.

Shakir M, Khatoon S, Parveen S, Azim Y. Metal ion prompted macrocyclic complexes derived from indole-2,3-dione (isatin) and orthophenylenediamine with their spectroscopic and antibacterial studies. Transition Met Chem 2007;32:42-6.

Chandra S, Pundir M. Metal ion prompted macrocyclic complexes derived from indole-2,3-dione (isatin) and orthophenylenediamine with their spectroscopic and antibacterial studies. Spectrochim Acta A 2008;69:1-7.

Radecka-Paryzek W, Patroniak V. Lisowski synthesis and characterisation of copper (II) complexes with Schiff bases of 2-hydroxy-1-naphyhaldehyde. Coord Chem Rev 2005;249:2156.

Saadeh SM. Synthesis, characterization and biological relevance of some metal (II) complexes with oxygen, nitrogen and oxygen (ONO) donor Schiff base ligand derived from thiazole and 2-hydroxy-1-naphthaldehyde. Arabian J Chem 2013;6:191-6.

Santos MA, Marques SM, Chaves S. Synthesis, characterization and biological relevance of some metal (II) complexes with oxygen, nitrogen and oxygen (ONO) donor Schiff base ligand derived from thiazole and 2-hydroxy-1-naphthaldehyde. Coord Chem Rev 2012;256:240-59.

Joseph J, Mehta BH. Synthesis, characterization and biological relevance of some metal (II) complexes with oxygen, nitrogen and oxygen (ONO) donor Schiff base ligand derived from thiazole and 2-hydroxy-1-naphthaldehyde. Russ J Coord Chem 2007;33:124-9.

Dong W, Yang Rand Yan L. Metal ion prompted macrocyclic complexes derived from indole-2,3-dione (Isatin) and orthophenylenediamine with their spectroscopic and antibacterial studies. Indian J Chem 2007;40A:202-6.

Chandra S, Gautum A, Tyagi M. Metal ion prompted macrocyclic complexes derived from indole-2,3-dione (isatin) and orthophenylenediamine with their spectroscopic and antibacterial studies. Trans Met Chem 2007;32:1079-84.

Bozic LT, Marotta E, Traldi P. Metal ion prompted macrocyclic complexes derived from indole-2,3-dione (isatin) and orthophenylenediamine with their spectroscopic and antibacterial studies. Polyhedron 2007;26:1663-8.

Singh I, Poonam Mrs. High sensitive and selective spectrophotometric method for the determination of trace level of Manganese in some real, environmental, biological, soil, food, fertilizer and pharmaceutical samples using bis (2-hydroxy-1-naphthaldehyde orhophenylenediamine. Am Chem Sci J 1984;31:109-12.

Yamane T. High sensitive and selective spectrophotometric method for the determination of trace level of Manganese in some real, environmental, biological, soil, food, fertilizer and pharmaceutical samples using bis (2-hydroxy-1-naphthaldehyde orhophenylenediamine. Anal Sci 1986;2:191-5.

Bahl BS, Bahl A. High sensitive and selective spectrophotometric method for the determination of trace level of Manganese in some real, environmental, biological, soil, food, fertilizer and pharmaceutical samples using bis (2-hydroxy-1-naphthaldehyde orhophenylenediamine. Elementary Organic Chemistry, Schand and Company Ltd., New Delhi; 2014;4:357-83.

Barboiu CT, Luca M, Pop C, Brewster E, Dinculescu EM. Complexes of Schiff bases derived from 2-hydroxyaldehyde and propane-1,2-diamine: synthesis, characterization and antibacterial Screening. Eur J Med Chem 1996;31:597.

Ilhan S, Temel H, Kilic A. Synthesis and characterization of copper(II) complexes with Schiff bases of 2-hydroxy-1-naphyhaldehyde. Chin J Chem 2008;61:277.

Lodeiro C, Bastida R, Bertolo E, Rodriguez A. Synthesis and characterization of copper(II) complexes with Schiff bases of 2-hydroxy-1-naphyhaldehyde. Can J Chem 2004;82:437.

Ilhan S, Temel H, Kilic A, Yilmaz I. Synthesis and characterization of macrocyclic Cd (II) complexes. Trans Met Chem 2007;32:344.

Chowdhury DA, Uddin MN, Hoque F. Complexes of schiff bases derived from 2-hydroxyaldehyde and propane-1,2-diamine: synthesis, characterization and antibacterial Screening. CMUJ Nat Sci 2011;10:216-68.

Ilhan S, Temel H, Yilmaz I, Sekerci M. Synthesis and characterization of macrocyclic Cd (II) complexes. Polyhedron 2007;26:2795.

Ilhan S, Temel H, Yilmaz I, Sekerci M. Synthesis and spectral characterization of macrocyclicPd (II) perchlorate complexes. J Org Met Chem 2007;47A:3855.

Chowdhury DA, Mohammad N, Uddin F Hoque, Chiang Mai J. Complexes of schiff bases derived from 2-hydroxyaldehyde and propane-1,2-diamine: synthesis characterization and antibacterial Screening. J Sci 2010;37:443-50.

Ilhan S, Temel H, Yilmaz I, Sekerci M. Synthesis and characterization of macrocyclic Cd (II) complexes. Polyhedron 2007;12:2795.

Chowdhury DA, Mohammad N, Uddin, Akter Md, Sarker H, Chiang Mai. Complexes of schiff bases derived from 2-hydroxyaldehyde and propane-1,2-diamine: synthesis, characterization and antibacterial Screening. J Sci 2008;35:483-94.

Ilhan S, Temel H, Kilic A, Tas E. Synthesis and characterization of macrocyclic Cd (II) complexes. Trans Metal Chem 2007;32:1012.

Published

01-11-2015

How to Cite

Angelo, A. N. P., L. R. Sharma, and K. N. Sabharwal. “SYNTHESIS, CHARACTERIZATION AND ELECTROCHEMICAL INVESTIGATION OF NOVEL 17-MEMBERED DIOXADIAZA NAPTHALDEHYDE BASED MACROCYCLIC LIGAND AND ITS COMPLEXES OF Co (III), Ni (II) AND Cu (II) PERCHLORATE IONS”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 7, no. 11, Nov. 2015, pp. 172-5, https://journals.innovareacademics.in/index.php/ijpps/article/view/8281.

Issue

Section

Original Article(s)