Zinc, copper and nickel complexes of a macrocycle synthesized from pyridinedicarboxylic acid: A spectroscopic, thermal and theoretical study

Main Article Content

Esmaiel Soleimani
Sayed Ali Naghi Taheri
Mohsen Sargolzaei

Abstract

The metal(II) ion complexes of a pentadentate macrocycle 1, namely 3,12-dioxa-6,9,18-triazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,13-dione are synthesized. This macrocycle is prepared from the reaction of dipotassium salt of 2,6-pyridinedicarboxylic acid with ethylenediamine and 1,2-dibromo­ethane. The reaction of 1 (L) in methanol with MCl2.xH2O gave complexes with the general formula [M(L)Cl2] (where M= Ni(II) 2, Cu(II) 3 and Zn(II) 4, respectively). The analysis of IR, 1H- and 13C-NMR spectral data of all complexes propose that 1 is bonded to metal(II) ions through a nitrogen atom of pyridine ring, two nitrogen atoms of amine groups and two oxygen atoms of ester moieties. The thermal analysis indicated that there are no water molecules of hydration or coordinated in the structure of the complexes. Among these complexes, the Cu(II) 3 complex demonstrated good antibacterial and antifun­gal activities. The molecular geometry, AIM atomic charge and frontier mole­cular orbitals of the compounds are investigated theoretically using DFT method. Based on the theoretical data of these complexes represented, a bipyr­amidal pentagonal arrangement can be envisaged in such a way that the N3O2 pentadentate donor sites form the planar pentagonal base of the bipyramid and the two Cl atoms occupy the vertexes.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Article Details

How to Cite
[1]
E. Soleimani, S. A. N. Taheri, and M. Sargolzaei, “Zinc, copper and nickel complexes of a macrocycle synthesized from pyridinedicarboxylic acid: A spectroscopic, thermal and theoretical study”, J. Serb. Chem. Soc., vol. 82, no. 6, pp. 665–680, Aug. 2017.
Section
Inorganic Chemistry

References

B. Zhao, X. Y. Chen, P. Cheng, D. Z. Liao, S. P. Yan, Z. H. Jiang, J. Am. Chem. Soc. 126 (2004) 1539

F. Mori, T. Nyui, T. Ishida, T. Nogami, K. Ychoi, H. Nojiri, J. Am. Chem. Soc. 128 (2006) 1440

J. M. Lehn, Supramolecular chemistry: Concepts and perspectives, Wiely–VCH, Weinheim, 1995

E. C. Constable, Coordination chemistry of macrocyclic compounds, Oxford University Press, Oxford, 1999

D. P. Singh, R. Kumar, V. Malik, P. Tyagi, Transition Met. Chem. 32 (2007) 1051

D. P. Singh, R. Kumar, V. Malik, P. Tyagi, J. Enzyme Inhib. Med. Chem. 22 (2007) 177

R. V. Singh, A. Chaudhary, J. Inorg. Biochem. 98 (2004) 1712

D. P. Singh, V. Malik, K. Kumar, C. Sharma, K. R. Aneja, Spectrochim. Acta A 76 (2010) 45

S. M. Abdallah, M. A. Zayed, G. G. Mohamed, Arab. J. Chem. 3 (2010) 103

M. Shakir, N. Shahid, N. Sami, M. Azam, A. U. Khan, Spectrochim. Acta A 82 (2011) 31

G. G. Mohamed, M. A. Badawy, M. M. Omar, M. M. Nassar, A. B. Kamel, Spectrochim. Acta A 77 (2010) 773

K. Kumar, M. Kamboj, K. Jain, D. P. Singh, Spectrochim. Acta A 128 (2014) 243

D. P. Singh, R. Parveen, R. Kumar, P. Surain, K. R. Aneja, J. Inclusion Phenom. Macrocyclic Chem. 78 (2014) 363

C. Ma, J. Li, R. Zhang, D. Wang, Inorg. Chim. Acta 358 (2005) 4575

B. Setlow, P. Setlow, Appl. Environ. Microbiol. 59 (1993) 640

J. T. Groves, I. O. Kady, Inorg. Chem. 32 (1993) 3868

E. Soleimani, J. Mol. Struct. 955 (2011) 1

E. Soleimani, J. Therm. Anal. Calorim. 115 (2014) 2191

A. D. Becke, J. Chem. Phys. 98 (1993) 5648

P. J. Hay, W. R. Wadt, J. Chem. Phys. 82 (1985) 270

Gaussian 03, Revision A.1, Gaussian Inc., Pittsburgh, PA, 2003

I. I. Dennington, T. Keith, J. Millam, Gauss View, Version 4.1.2, Semichem Inc., Shawnee Mission, KS, 2007.

R. J. Parr, R. G. Pearson, J. Am. Chem. Soc. 105 (1983)7512

W. J. Geary, Coord. Chem. Rev. 7 (1971) 81

M. Salavati-Niasari, Chem. Lett. 34 (2005) 1444

M. Salavati-Niasari, M. Rezai-Adaryni, S. Heydarzadeh, Transition Met. Chem. 30 (2005) 445

Z. R. Ranjbar, A. Morsali, J. Mol. Struct. 936 (2009) 206

K. Nakamoto, Infrared and raman spectroscopy of inorganic and coordination compounds, Wiley–Interscience, New York, 1978

A. S. Attia, M. F. El-Shahat, Polyhedron 26 (2007) 791

M. Salavati-Niasari, A. Amiri, J. Mol. Catal., A: Chem. 235 (2005) 114

M. Salavati-Niasari, A. Amiri, Transition Met. Chem. 30 (2005) 720

M. Salavati-Niasari, F. Davar, Inorg. Chem. Commun. 9 (2006) 175

A. Husain, S. A. A. Nami, K. S. Siddiqi, Spectrochim. Acta, A 73 (2009) 89

S. Khan, S. A. A. Nami, K. S. Siddiqi, J. Organomet. Chem. 693 (2008) 1049

S. Sarkar, K. Dey, Spectrochim. Acta A 77 (2010) 740

F. Marandi, L. Saghatforoush, I. Pantenburg, G. Meyer, J. Mol. Struct. 938 (2009) 277

A. Moghimi, M. Ranjbar, H. Aghabozorg, F. Jalali, M. Shamsipur, G. P. A. Yap, H. Rahbarnoohi, J. Mol. Struct. 605 (2002) 133

B. Geeta, K. Shravankumar, P. M. Reddy, E. Ravikrishna, M. Sarangapani, K. K. Reddy, V. Ravinder, Spectrochim. Acta A 77 (2010) 911

E. Pretsch, T. Clerc, J. Seibl, W. Simon, Tables of spectral data for structure determination of organic compounds, 2nd ed., Springer, Berlin, 1989.

A. B. P. Lever, Inorganic electronic spectroscopy, 2nd ed., Elsevier, Amsterdam, 1984

R. A. Levenson, R. J. G. Dominguez, Inorg. Chem. 12 (1973) 2342

M. M. Omar, G. G. Mohamed, A. A. Ibrahim, Spectrochim. Acta A 73 (2009) 358

N. M. Agh-Atabay, B. Dulger, F. Gucin, Eur. J. Med. Chem. 40 (2005) 1096

M. A. Ali, A. H. Mirza, W. B. Ejau, P. V. Bernhardt, Polyhedron 25 (2006) 3337

M. G. B. Drew, J. Nelson, S. M. Nelson, J. Chem. Soc., Dalton Trans. (1981) 1685

M. Sumar, I. Ivanovic-Burmazovic, I. Hodzic, K. Andjelkovic, Synth. React. Inorg. Met.--Org. Chem. 32 (2002) 721

O. A. El-Gammal, T. H. Rakha, H. M. Metwally, G. M. Abu El-Reash, Spectrochim. Acta A 127 (2014) 144

O. A. El-Gammal, M. M. Bekheit, S. A. El-Brashy, Spectrochim. Acta A 137 (2015) 207

B. H. M. Mruthyunjayaswamy, B. I. Omkar, Y. Jadegoud, J. Braz. Chem. Soc. 16 (2005) 783

A. Lakshmi, V. Balachandran, J. Mol. Struct. 1033 (2013) 40

M. Gaber, H. El-Ghamry, F. Atlam, S. Fathalla, Spectrochim. Acta, A 137 (2015) 919.