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N,N′-dipyridoxyl(ethylenediamine) schiff-base ligand and its square-pyramidal copper(II) complex: Synthesis, experimental and theoretical characterization

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Abstract

A new tetradentate N,N′-dipyridoxyl(1,2-ethylenediamine) [=H2ES] Schiff-base ligand and its Cu(II) salen complex [Cu(ES)(H2O)] are synthesized and characterized by IR, UV-Vis, 1H NMR, mass spectrometry, and elemental analysis. Their optimized geometries and theoretical vibrational frequencies are computed by using the density functional theory method where the B3LYP functional was used. Also, the 1H NMR chemical shifts of the H2ES ligand are calculated at the same computational level. In the optimized structure of the free ligand, two pyridine rings are not in the same plane. In the structure of the complex, the Schiff-base ligand acts as a dianionic tetradentate ligand in the N, N, O−, O− manner, so that the coordinating atoms occupy equatorial positions. The H2O ligand occupies the axial position of the squarepyramidal complex. The calculated results are consistent with the experimental ones, confirming the suitability of the optimized structures for the H2ES ligand and its Cu(II) complex.

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References

  1. D. Yu, H. Xiaoxia, S. Xiaoli, and Z. Zhiling, Wuhan Univ. J. Nat. Sci., 15, No. 2, 165–170 (2010).

    Article  Google Scholar 

  2. D. Kumar, P. K. Gupta, and A. Syamal, J. Chem. Sci., 117, No. 3, 247–253 (2005).

    Article  CAS  Google Scholar 

  3. D. L. Chizhov, E. F. Khmara, P. A. Slepukhin, V. I. Filyakova, and V. N. Charushin, J. Struct. Chem., 51, No. 2, 288–295 (2010).

    Article  CAS  Google Scholar 

  4. A. Valent, M. Melník, D. Hudecová, B. Dudová, R. Kivekäs, and M. R. Sundberg, Inorg. Chim. Acta, 340, 15–20 (2002).

    Article  CAS  Google Scholar 

  5. W. Wang, F. X. Zhang, J. Li, and W. B. Hu, Russ. J. Coord. Chem., 35, No. 6, 429–432 (2009).

    Article  CAS  Google Scholar 

  6. V. I. Ovcharenko, S. V. Fokin, G. V. Romanenko, V. N. Ikorskii, V. A. Reznikov, and A. V. Podoplelov, J. Struct. Chem., 38, No. 4, 626–636 (1997).

    Article  CAS  Google Scholar 

  7. J. R. Morrow and K. Kolasa, Inorg. Chim. Acta., 195, No. 2, 245–248 (1992).

    Article  CAS  Google Scholar 

  8. A. Bottcher, T. Takeuchi, K. I. Hardcastle, T. J. Meade, and H. B. Gray, Inorg. Chem., 36, No. 12, 2498–2504 (1997).

    Article  Google Scholar 

  9. G. Liu, J. Peiliao, S. Huang, G. Lishen, and R. Qinyu, Anal. Sci., 17, No. 9, 1031–1036 (2001).

    Article  Google Scholar 

  10. E. M. Hodnett and P. D. Mooney, J. Med. Chem., 13, No. 4, 786–788 (2001).

    Article  Google Scholar 

  11. S. Dadfarnia, A. M. Haji Shabani, F. Tamadon, and M. Rezaei, Microchim. Acta, 158, Nos. 1/2, 159–163 (2007).

    Article  CAS  Google Scholar 

  12. S. Sadeghi, A. Gafarzadeh, and H. Naeimi, J. Anal. Chem., 61, No. 7, 677–682 (2006).

    Article  CAS  Google Scholar 

  13. K. C. Gupta and A. K. Sutar, J. Mol. Catal. A: Chem., 272, Nos. 1/2, 64–74 (2007).

    Article  CAS  Google Scholar 

  14. K. C. Gupta and A. K. Sutar, React. Funct. Polym., 68, No. 1, 12–26 (2008).

    Article  CAS  Google Scholar 

  15. A. Sakthivel, W. Sun, G. Raudaschl-Sieber, A. S. T. Chiang, M. Hanzlik, and F. E. Kühn, Catal. Commun., 7, No. 5, 302–307 (2006).

    Article  CAS  Google Scholar 

  16. J. D. Koola and J. K. Kochi, Inorg. Chem., 26, No. 6, 908–916 (1987).

    Article  CAS  Google Scholar 

  17. C. Baleizäo and H. Garcia, Chem. Rev., 106, No. 9, 3987–4043 (2006).

    Article  Google Scholar 

  18. L. Canali and D. C. Sherrington, Chem. Soc. Rev., 28, 85–93 (1999).

    Article  CAS  Google Scholar 

  19. D. M. C. R. Maria, J. M. Gonçalves, A. L. R. S. Silva, P. C. F. C. Oliveira, B. Schröder, and M. A. V. da silva, J. Mol. Catal. Chem., 224, Nos. 1/2, 207–212 (2004).

    Google Scholar 

  20. K. C. Gupta and A. K. Sutar, Coord. Chem. Rev., 252, Nos. 12–14, 1420–1450 (2008).

    Article  CAS  Google Scholar 

  21. S. Routier, J.-L. Bernier, M. J. Waring, P. Colson, C. Houssier, and C. Bailly, J. Org. Chem., 61, No. 7, 2326–2331 (1996).

    Article  CAS  Google Scholar 

  22. S. Routier, J.-L. Bernier, J.-P. Catteau, P. Colson, C. Houssier, C. Rivalle, E. Bisagni, and C. Bailly, Bioconjugate Chem., 8, No. 6, 789–792 (1997).

    Article  CAS  Google Scholar 

  23. E. Lamour, S. Routier, J.-L. Bernier, J.-P. Catteau, C. Bailly, and H. Vezin, J. Am. Chem. Soc., 121, No. 9, 1862–1869 (1999).

    Article  CAS  Google Scholar 

  24. D. G. Peters and M. J. Samide, J. Electroanal. Chem., 443, No. 1, 95–102 (1998).

    Article  Google Scholar 

  25. S. Striegler, M. G. Gichinga, and M. Dittel, Org. Lett., 10, No. 2, 241–244 (2008).

    Article  CAS  Google Scholar 

  26. I. Owsik, B. N. Kolarz, and J. Jezierska, Catal. Lett., 107, Nos. 3/4, 197–203 (2006).

    Article  CAS  Google Scholar 

  27. H. Eshtiagh-Hosseini, M. R. Housaindokht, S. A. Beyramabadi, S. Beheshti, A. A. Esmaeili, M. Javan-Khoshkholgh, and A. Morsali, Spectrochim. Acta Part A, 71, No. 4, 1341–1347 (2008).

    Article  Google Scholar 

  28. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, No. 2, 785–789 (1988).

    Article  CAS  Google Scholar 

  29. M. J. Frisch et al., Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh PA (1998).

    Google Scholar 

  30. R. Ditchfield, Mol. Phys., 27, No. 4, 789–807 (1974).

    Article  CAS  Google Scholar 

  31. D. C. Young, Computational Chemistry: A Practical Guide for Applying Techniques to Real-World Problems, John Wiley & Sons, Inc. (2001).

  32. D. Yu, L. Zhiwei, and Z. Zhonghai, Acta Chim. Sinica, 65, No. 8, 655–659 (2007).

    Google Scholar 

  33. D. Kumari, A. Syamal, J. Lalit, and K. Sharma, J. Chem. Sci., 121, No. 1, 57–64 (2009).

    Article  Google Scholar 

  34. L. Mouni, M. Akkurt, S. Ö. Yıldırım, T. Ben Hadda, and Z. H. Chohan, J. Chem. Crystallogr., 40, No. 2, 169–172 (2010).

    Article  CAS  Google Scholar 

  35. M. J. Al-Jeboori, H. A. Hasan, and W. A. J. Al-Sa’idy, Trans. Met. Chem., 34, No. 6, 593–598 (2009).

    Article  CAS  Google Scholar 

  36. R. Deters and R. Krämer, Inorg. Chim. Acta, 269, No. 1, 117–124 (1998).

    Article  CAS  Google Scholar 

  37. A. Biswas, M. G. B. Drew, and A. Ghosh, Polyhedron, 29, No. 3, 1029–1034 (2010).

    Article  CAS  Google Scholar 

  38. B. Liu, H. Zhou, Z. Pan, H. Zhang, J. Hu, X. Hu, H. Zhou, and Y. Song, Trans. Met. Chem., 30, No. 8, 1020–1026 (2005).

    Article  CAS  Google Scholar 

  39. N. H. Patel, H. M. Parekh, and M. N. Patel, Trans. Met. Chem., 30, No. 1, 13–17 (2005).

    Article  CAS  Google Scholar 

  40. G. Soto-Garrido and V. Salas-Reyes, Trans. Met. Chem., 25, No. 2, 192–195 (2000).

    Article  CAS  Google Scholar 

  41. S. Parimala, K. N. Gita, and M. Kandaswamy, Polyhedron, 17, No. 19, 3445–3453 (1998).

    Article  CAS  Google Scholar 

  42. Z. L. You, Acta Crystallogr., C61, m406–m408 (2005).

    CAS  Google Scholar 

  43. G. R. Yue, X. J. Xu, Y. Z. Shi, and L. Feng, Acta Crystallogr., E61, m693/m694 (2005).

    CAS  Google Scholar 

  44. F. M. Nie, Z. M. Wang, Y. M. Li, Y. F. Zhao, and C. H. Yan, Acta Crystallogr., C54, 1853–1855 (1998).

    CAS  Google Scholar 

  45. R. T. Stibrany and J. A. Potenza, J. Chem. Crystallogr., 39, No. 4, 266–269 (2009).

    Article  CAS  Google Scholar 

  46. M. S. Ray, R. Bhattacharya, S. Chaudhuri, L. Righi, G. Bocelli, G. Mukhopadhyay, and A. Ghosh, Polyhedron, 22, No. 4, 617–624 (2003).

    Article  CAS  Google Scholar 

  47. H. Dal, Y. Süzen, and E. Şahin, Spectrochim. Acta Part A, 67, Nos. 3/4, 808–814 (2007).

    Google Scholar 

  48. S. Zolezzi, A. Decinti, and E. Spodine, Polyhedron, 18, No. 6, 897–904 (1999).

    Article  CAS  Google Scholar 

  49. Y.-L. Zhang, W.-J. Ruan, X.-J. Zhao, H.-G. Wang, and Z.-A. Zhu, Polyhedron, 22, No. 4, 1535–1545 (2003).

    Article  CAS  Google Scholar 

  50. F. Gao, W.-J. Ruan, J.-M. Chen, Y.-H. Zhang, and Z.-A. Zhu, Spectrochim. Acta Part A, 62, Nos. 6/7, 886–895 (2005).

    Google Scholar 

  51. A. Pui, C. Policar, and J.-P. Mahy, Inorg. Chim. Acta, 360, No. 6, 2139–2144 (2007).

    Article  CAS  Google Scholar 

  52. D. Avcı, Y. Atalay, M. Şekerci, and M. Dinçr, Spectrochim. Acta Part A, 73, No. 1, 212–217 (2009).

    Article  Google Scholar 

  53. A. A. Khandar, B. Shaabani, F. Belaj, and A. Bakhtiari, Polyhedron, 25, No. 9, 1893–1900 (2006).

    Article  CAS  Google Scholar 

  54. J. Sanmartín, A. M. García-Deibe, M. Fondo, D. Navarro, and M. R. Bermejo, Polyhedron, 23, No. 6, 963–967 (2004).

    Article  Google Scholar 

  55. D. C. Ware, D. S. Mackie, P. J. Brothers, and W. A. Denny, Polyhedron, 14, No. 12, 1641–1646 (1995).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    S. A. Beyramabadi, A. Morsali & S. H. Vahidi

  2. Department of Chemistry, Faculty of Science, Birjand University, Birjand, Iran

    M. J. Khoshkholgh & A. A. Esmaeili

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  1. S. A. Beyramabadi
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  2. A. Morsali
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  3. S. H. Vahidi
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  4. M. J. Khoshkholgh
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  5. A. A. Esmaeili
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Correspondence to S. A. Beyramabadi.

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Original Russian Text Copyright © 2012 by S. A. Beyramabadi, A. Morsali, S. H. Vahidi, M. J. Khoshkholgh, A. A. Esmaeili

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 53, No. 3, pp. 466–473, May–June, 2012.

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Beyramabadi, S.A., Morsali, A., Vahidi, S.H. et al. N,N′-dipyridoxyl(ethylenediamine) schiff-base ligand and its square-pyramidal copper(II) complex: Synthesis, experimental and theoretical characterization. J Struct Chem 53, 460–467 (2012). https://doi.org/10.1134/S0022476612030079

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