Mononuclear Nickel(II) and Zinc(II) Complexes with N-(2-propanamide)-2-picolylamine ligand: Synthesis, Chromotropism Properties and DFT Calculations

Document Type : Research Paper

Authors

Department of Chemistry, University of Mazandaran, Babol-sar 47416-95447, Iran

10.22036/icr.2023.389361.1142

Abstract

Two nickel(II), and zinc(II) complexes [ML2](ClO4)2 of N-(2-propanamide)-2-picolylamine , L, derived from the condensation reaction of 2-picolylamine with acrylamide were synthesized. The prepared complexes were characterized by elemental analyses, ultraviolet-visible, infrared, 1-H-NMR spectroscopy techniques, and conductivity measurements. The ligand behaves like an NNO donor set, forming octahedral geometries with both Ni(II) and Zn(II) complexes. The nickel complex is halochromic. pH effects on the visible absorption spectra of the nickel complex were investigated in the range of 2-13. Its color change was due to the protonation and deprotonation of labile moieties of the ligand at room temperature. The complex displayed reversible thermochromism in solvents of DMSO and DMF attributed to the dissociation of hemilabile amide moieties from the metal center and substituted by solvent molecules. For the purpose of assigning experimental data to the ligands and complexes, a density function theory calculation on the level of B3LYP/LanL2DZ was performed.

Graphical Abstract

Mononuclear Nickel(II) and Zinc(II) Complexes with N-(2-propanamide)-2-picolylamine ligand: Synthesis, Chromotropism Properties and DFT Calculations

Keywords

References

  1. P. Braunstein, F. Naud, Angew. Chem. Int. Ed. 2001, 40, 680-699.
  2. G.M. Adams, A.S. Weller, Coord. Chem. Rev. 2018, 355, 150-172.
  3. C.S. Slone, D.A. Weinberger, C.A. Mirkin, Prog. Inorg. Chem. 1999, 48, 233-350.
  4. A. Bader, E. Lindner, Coord. Chem. Rev. 1991, 108, 27-110.
  5. E. Lindner, S. Pautz, M. Haustein, Coord. Chem. Rev. 1996, 155, 145-162.
  6. K.D. Hesp, D. Wechsler, J. Cipot, A. Myers, R. McDonald, M.J. Ferguson, G. Schatte, M. Stradiotto, Organometal. 2007, 26, 5430-3437.
  7. J. Duran, D. Oliver, A. Polo, J. Real, J. Benet-Buchholz, X. Fontrodona, Tetrahedron: Asymmetry 2003, 14, 2529-2538.
  8. Y.S. Uh, A. Boyd, V.R. Little, P.G. Jessop, K.D. Hesp, J. Cipot-Wechsler, M. Stradiotto, R. McDonald, J. Organomet. Chem. 2010, 695, 1869-1872.
  9. M.J. Wiester, C.A. Mirkin, Inorg. Chem. 2009, 48, 8054-8056.
  10. E. Lindner, I. Warad, K. Eichele, H.A. Mayer Inorg. Chim. Acta 2003, 350, 49-56.
  11. S.E. Angell, C.W. Rogers, Y. Zhang, M.O. Wolf, Jr. W.E. Jones, Coord. Chem. Rev. 2006, 250, 1829-1841.
  12. L. Rostami, H. Golchoubian, J. Coord. Chem. 2017, 70, 3660-3676.
  13. M. Ghoreishi Amiri, H. Golchoubian, J. Mol. Struct. 2018, 1165, 196-205.
  14. H. Golchoubian, A. Heidarian, E. Rezaee, F. Nicolò, Days & Pigments 2014, 104, 175-184.
  15. Y. Fukuda, Inorganic Chromotropism: Basic Concepts and Applications of Colored Materials, Springer, Germany, 2007.
  16. U. El-Ayaan, F. Murata, Y. Fukuda, Monatshe. Chem. 2001, 132, 1279-1294.
  17. H. Golchoubian, S. Nateghi, J. Coord. Chem. 2016, 69, 3192-3205.
  18. A. Shirvan, H.  Golchoubian,  E.  Bouwman,  J. Mol.

       Struct. 2019, 1195, 769-777.

  1. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09. Revision A. 1, Gaussian Inc., Wallingford, USA 2009.
  2. R. Dennington, T. Keith, J. Millam, GaussView, Version 5, Semichem Inc., Shawnee Mission, 2009.
  3. B.P. Pritchard, D. Altarawy, B. Didier, T.D. Gibson, T.L. Windus, J. Chem. Info. Model, 2019, 59, 4814-4820.
  4. W.-Y. Wang, X.-F. Du, N.-N. Ma, S.-L. Sun, Y.-Q. Qiu, J. Mol. Model. 2013, 19, 1779-1787.
  5. B. Machura, J.G. Małecki, A.S. Witlicka, I. Nawrot, R. Kruszynski, Polyhedron 2011, 30, 864-872.
  6. F. Billes, A. Holmgren, H. Mikosch, Vib. Spectrosc. 2010, 53, 296-306.
  7. Z. Demircioglu, C.A. Kastas, O. Buyukgungor, Spectrochim. Acta A 2015, 139, 539-548.
  8. J. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976.
  9. K. Fukui, Science 1982, 218, 747-754.
  10. C.J. Brabec, N.S. Sariciftci, J.C. Hummelen, Adv. Funct. Mater. 2001, 11, 374-380.
  11. E.E. Ebenso, T. Arslan, F. Kandemirli, I. Love, C. Ogretir, M. Saracoglu, S.A. Moron, Int. J. Quantum. Chem. 2010, 110, 2614-2636. 
  12. H. Golchoubian, E. Rezaee, J. Mol. Struct. 2009, 927, 91-95.
  13. Y. Fukuda, A. Shimura, M. Mukaida, E. Fujita, K. Sone, J. Inorg. Nucl. Chem. 1974, 36, 1265-1270.
  1. W.J. Geary, Coord. Chem. Rev., 1971, 7, 81-122.
  2. J.R. Hartman, R.W. Vachet, J.H. Callahan, Inorg. Chim. Acta 2000, 297, 79-87.
  3. S. Kazemi, H. Golchoubian, Inorg. Chem. Res., 2020, 4, 76-85.
  4. A.B.P. Lever, Inorganic Electronic Spectroscopy, 2nd edn., Elsevier, Amsterdam, 1984.
  5. G. Bruhn, E.R. Davidson, I. Mayer, A.E. Clark, Chem. Rev. 2006, 106, 2065-2072.
  6. E. Ebenso, M.M. Kabanda, T. Arslan, M. Saracoglu, F. Kandemirli, L.C. Murulana, A.K. Singh, S.K. Shukla, B. Hammouti, K.F. Khaled, M.A. Quraishi, I.B. Obot, N.O. Edd, Int. J. Electrochem. Sci. 2012, 7, 5643-5676.
  7. I. Sheikhshoaie, S.Y. Ebrahimipour, A. Crochet, K. Fromm, Synthesis, Res. Chem. Intermed. 2015, 41, 1881-1891.
  8. A. Atac, C. Karaca, S. Gunnaz, M. Karabacak, Spectrochim. Acta A 2014, 130, 516-525.
  9. R.G. Wilkines, Kinetics and mechanism of reaction of transition metal complexes 2nd Ed. Wiely-VCH Verlag GmbH & Co KGaA, Weinheim, 2002.
Inorganic Chemistry Research
Volume 6, Issue 2
December 2022
Pages 146-154

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History

  • Receive Date: 11 March 2023
  • Revise Date: 01 May 2023
  • Accept Date: 03 May 2023

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