Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions

COBAN, BURAK; AĞAC, Hakan; EROGLU, EROL; ŞENGÜL, ABDURRAHMAN

Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions

Abdurrahman ŞENGÜL, (Karaelmas Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Zonguldak, Türkiye)

Hakan AĞAC, (Karaelmas Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Zonguldak, Türkiye)

Burak ÇOBAN, (Karaelmas Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Zonguldak, Türkiye)

Erol EROĞLU (Harran Üniversitesi, Fen Edebiyat Fakültesi, Şanlıurfa, Türkiye)

Turkish Journal of Chemistry

1 0

Yıl: 2011 Cilt: 35 Sayı: 1 Sayfa Aralığı: 25 - 36 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions

Öz:

The tetradentate ligand 6,6' -diacetyl-2,2' -bipyridine dioxime (L) was obtained in high yield by the condensation reaction of 6,6' -diacetyl-2,2'-bipyridine with hydroxyl amine in alkaline solution. Density functional calculations and 3D modeling of the structure at the B3LYP/6-31G(d) level of theory for L revealed that the energy difference between the global trans conformer (trans-L), which possesses the C2h point group, and the distorted cis conformer (cis-L) was 5.214 kcal/mol. Synthesis and characterization of the metal complexes with Cu(I), Cu(II), Pt(II), and Pd(II) metal ions were reported. L acted as a N4 - donor ligand to coordinate to the metal centers via N atoms of the 2,2 -bipyridine and the imine moieties to afford tetrahedral complex [CuI L]PF6 (1), distorted octahedral complex [CuII L(OH2)2 ](NO3)2 (2), and square-planar complexes [Pt II L]Cl 2 (3) and [PdII L]Cl (4), respectively. The CHN analysis for 1 implies that L coordinated to 2 copper(I) ions as a bridging ligand to form a dinuclear metal complex, [Cu2L2 ]2+ , due to the twisting of the coordinated bonds exposed by the tetrahedral geometry preference for the metal ion. The ligand formed intramolecular hydrogen bonds between the oxime groups in 4, as revealed by the spectroscopic studies. The most stable conformations of the compounds were obtained by using the molecular mechanics optimization feature in CAChe software with an augmented MM2 force field. 1

Anahtar Kelime:

Konular: Mühendislik, Kimya

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. CAChe$circledR$ 6.1.10 for Windows, Oxford Molecular Limited, 1989-2000, Fujitsu Limited, Japan, 2000-2004.
2. Chakravorty, A. Coord. Chem. Rev. 1974, 13, 1-46.
3. (a) Sreerama, G. S.; Pal, S. Inorg. Chem. 2002, 41, 4843-4845.
4. (b) Datta, D.; Chakravorty, A. Inorg. Chem. 1982, 21, 363-368.
5. (c) Wan, S.; Mori, W.; Yamada, S.; Murahashi, I. S. Bull. Chem. Soc. Jpn. 1989, 62, 435-438.
6. (a) Mohanty, G. J.; Singh, P. R.; Chakravorty, A. Inorg. Chem. 1975, 14, 2178-2183.
7. (b) Singh, N. A.; Singh, R. P.; Mohanty, G. J.; Chakravorty, A. Inorg. Chem. 1977, 16, 259-2601.
8. (c) Mohanty, G. J.; Chakravorty, A. Inorg. Chem. 1976, 15, 2912-2916.
9. (a) Kukuskin, Y. Y.; Nishioka, T.; Tudela, T.; Isobe, K.; Kinoshita, I. Inorg. Chem. 1997, 36, 6157-6165.
10. Naskar, S.; Mishra, D.; Butcher, J. R.; Chattopadhyay, K. S. Polyhedron 2007, 26, 3703-3714.
11. Bertalosi, V.; Gilli, G.; Veronese, A. Acta Cryst. 1982, B38, 502-511.
12. Bachechi, F.; Zambonelli, L. Acta Cryst. 1973, B29, 2598-2600.
13. Burton, A. E.; Brammer, L.; Pigge, C. F.; Aaker¨oy, B.C.; Leinen, S. D. New J. Chem. 2003, 27, 1084-1094.
14. Braga, D.; Maini, L.; Polito, M.; Scaccianoce, L.; Cojazzi, G.; Grepioni, F. Coord. Chem. Rev. 2001, 216-217, 225-248.
15. Kudüva, S. S.; Blaser, D.; Boese, R.; Desiraju, R. G. J. Org. Chem. 2001, 66, 1621-1626.
16. Tremayne, M.; Glidewell, C. Chem. Commun. 2000, 2425-2426.
17. Milios, J. C.; Stamatatos, C. T.; Perlepes, P. S. Polyhedron 2006, 25, 134-194.
18. Sengul, A.; Hursthouse, B. M.; Coles, J. S.; Gillard, D. R. Acta Cryst. 1998, C54, 661-662.
19. Ziessel, R. Coord. Chem. Rev. 2001, 216-217, 195-223.
20. Couchman, M. S.; Jeffery, C. J.;Ward, D. M. Polyhedron 1999, 18, 2633-2640.
21. Simpson, P. G.; Vinciguerra, A.; Quagliano, J. V. Inorg. Chem. 1963, 2, 282-286.
22. Renouard, T.; Fallahpour, A. R.; Nazeeruddin, K. M.; Baker, H. R.; Gorelsky, I. S.; Lever, B. P. A.; Gratzel, M. Inorg. Chem. 2002, 41, 367-378.
23. Glynn, C. W.; Turnbull, M. M. Trans. Met. Chem. 2002, 27, 822-831. 24. Parks, J. E.; Wagner, B. E.; Holm, R. H. J. Organomet. Chem. 1973, 56, 53-66.
25. Günzler, H.; Gremlich, H. U. IR Spectroscopy,Wiley-VCH, 2002.
26. Sarıkavaklı, N.; İrez, G. Turk. J. Chem. 2005, 29, 107-115.
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.;Martin, R. L.; Fox, D.; Keith, J. T.; Al-Laham,M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.05, Gaussian, Inc., Pittsburgh, 2003.
28. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
29. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
30. Fukuchi, T. Bull. Chem. Soc. Jpn. 1992, 65, 1807-1811.
31. Szczepura, F. L.; Muller, J. G.; Bessel, A. C.; See, F. R,; Janik, S. T.; Churchill, R. M.; Takeuchi, J. K. Inorg. Chem. 1992, 31, 859-869.
32. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley, New York, 1986.
33. Middleton, R.; Thornback, J. R.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1980, 174-179.
34. Llanguri, R.; Morris, J. J.; Stanley, C. W.; Bell-Loncella, T. E.; Turner, M.; Boyko, J. W.; Bessel, A. C. Inorg. Chim. Acta 2001, 315, 53-65.
35. Babahan, İ.; Anıl, H.; Sarıkavaklı, N. Turk. J. Chem. 2006, 30, 563-571.
36. S¸engül, A.; Wang, J. W.; Coles, J. S. Polyhedron 2009, 28, 69-76.

APA	ŞENGÜL A, AĞAC H, COBAN B, EROGLU E (2011). Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions. , 25 - 36.
Chicago	ŞENGÜL ABDURRAHMAN,AĞAC Hakan,COBAN BURAK,EROGLU EROL Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions. (2011): 25 - 36.
MLA	ŞENGÜL ABDURRAHMAN,AĞAC Hakan,COBAN BURAK,EROGLU EROL Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions. , 2011, ss.25 - 36.
AMA	ŞENGÜL A,AĞAC H,COBAN B,EROGLU E Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions. . 2011; 25 - 36.
Vancouver	ŞENGÜL A,AĞAC H,COBAN B,EROGLU E Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions. . 2011; 25 - 36.
IEEE	ŞENGÜL A,AĞAC H,COBAN B,EROGLU E "Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions." , ss.25 - 36, 2011.
ISNAD	ŞENGÜL, ABDURRAHMAN vd. "Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions". (2011), 25-36.

APA	ŞENGÜL A, AĞAC H, COBAN B, EROGLU E (2011). Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions. Turkish Journal of Chemistry, 35(1), 25 - 36.
Chicago	ŞENGÜL ABDURRAHMAN,AĞAC Hakan,COBAN BURAK,EROGLU EROL Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions. Turkish Journal of Chemistry 35, no.1 (2011): 25 - 36.
MLA	ŞENGÜL ABDURRAHMAN,AĞAC Hakan,COBAN BURAK,EROGLU EROL Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions. Turkish Journal of Chemistry, vol.35, no.1, 2011, ss.25 - 36.
AMA	ŞENGÜL A,AĞAC H,COBAN B,EROGLU E Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions. Turkish Journal of Chemistry. 2011; 35(1): 25 - 36.
Vancouver	ŞENGÜL A,AĞAC H,COBAN B,EROGLU E Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions. Turkish Journal of Chemistry. 2011; 35(1): 25 - 36.
IEEE	ŞENGÜL A,AĞAC H,COBAN B,EROGLU E "Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions." Turkish Journal of Chemistry, 35, ss.25 - 36, 2011.
ISNAD	ŞENGÜL, ABDURRAHMAN vd. "Structural studies of complex compounds of 6,6' -diacetyl-2,2' -bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions". Turkish Journal of Chemistry 35/1 (2011), 25-36.