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COMPETITION OF OXYGEN- AND NITROGEN-DONOR LIGANDS IN THE SYNTHESIS OF COMPLEX COMPOUNDS OF COPPER WITH 2-(PHENYL-4-CHLOROPHENYLACETYL)INDANDIONE-1,3

https://doi.org/10.32362/2410-6593-2018-13-6-60-68

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Abstract

The interaction of CuCl and 2-(phenyl-4-chlorophenylacetyl)indandione-1,3 (HL, C23H15ClO3) in a mixed organic solvent (CH3CN, C5H5N, EtOH) gave a solvated crystal complex of copper(II) of composition [Cu(C2H5OH)(L)2]•C2H5OH (I). The isolated compound was investigated by X-ray and IR spectroscopy methods. Lattice parameters of (I): space gr. P21/c, a = 14.982(1), b = 14.558(1), с = 20.608(2) Å; β= 105.176(2)°; Z = 4 (Z′=1). It is established that the structural units in the crystal structure of the obtained compounds are the neutral square-planar coordination spheres of Cu(II) with cis-oriented deprotonated indandionate ligands L. The spheres are located in the space pairwise. One molecule of EtOH is included in the internal sphere of the complex, and the second is a bridge that unites the coordination centers due to the hydrogen bonds between the hydrogen atom of the hydroxo group of the coordinated alcohol and the O-atom of the keto group of the adjacent bis-chelate. This results in a dimer structure. At the same time, in addition to ethanol, molecules of other co-solvents (CH3CN, C5H5N) do not participate in complex formation and do not form solvates. It was found that a copper(II) complex is formed from copper(I) chloride. When using copper(I) iodide as a starting compound in ethanol in the presence of pyridine the formation of the chelate with the deprotonated ligand HL is not observed.

About the Authors

L. A. Nosikova
MIREA - Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)
Russian Federation

Ph.D. (Chemistry), Associate Professor, K.A. Bolshakov Chair of Chemistry and Technology of Rare and Scattered Elements, Nanoscale and Composite Materials

86, Vernadskogo Pr., Moscow 119571, Russia

ResearcherID: 679715



A. N. Kochetov
MIREA - Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)
Russian Federation

Ph.D. (Chemistry), Senior Lecturer, A.N. Reformatsky Chair of Inorganic Chemistry

86, Vernadskogo Pr., Moscow 119571, Russia

ResearcherID: 213376



Z. A. Kudryashova
MIREA - Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)
Russian Federation

Ph.D. (Chemistry), Associate Professor, A.N. Reformatsky Chair of Inorganic Chemistry

86, Vernadskogo Pr., Moscow 119571, Russia



A. Yu. Tsivadze
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences (IPCE RAS)
Russian Federation

Academician, D.Sc. (Chemistry), Professor, Head of the Laboratory of New Physicochemical Problems

31 Leninsky prospect, Moscow 119071, Russia

ResearcherID: G-7422-2014



References

1. Gavrielatos E., Mitsos C., Athanasellis G., Heaton B.T., Steiner A., Bickley J.F., IgglessiMarkopoulou O., Markopoulos J. Copper(II), cobalt(II), nickel(II) and zinc(II) complexes containing the enolate of N-acetyl-3-butanoyltetramic acid (Habta) and its phenylhydrazone derivative analogues. Crystal structure of [Cu(abta)2(py)2]·2H2O. J. Chem. Soc., Dalton Trans. 2001: 639-644.

2. Ahmedova A., Mantarevay V., Enchev V., Mitewa M. 2-Acetylindan-1,3-dione and its Cu2+ and Zn2+ complexes as promising sunscreen agents. Int. J. Cosmetic Sci. 2002; 24: 103-110.

3. Ahmedova A., Vaz M.G.F., Ciattini S., Gochev G., Caneschi A., Mitewa M. X-ray and EPR study on copper(II) complexes with an enamine ligand. Cent. Eur. J. Chem. 2005; 3(1): 146-156.

4. Kuo P.-Y., Shie T.-L., Chen Y.-S., Lai J.-T., Yang D.-Y. Enzyme inhibition potency enhancement by active site metal chelating and hydrogen bonding induced conformationrestricted cyclopropanecarbonyl derivatives. Bioorg. & Med. Chem. Lett.. 2006; 16: 6024-6027.

5. Teotonio E.E.S., Brito H.F., Viertler H., Faustino W.M., Malta O.L., de Sá G.F., Felinto M.C.F.C., Santos R.H.A., Cremona M. Synthesis and luminescent properties of Eu3+-complexes with 2-acyl1,3-indandionates (ACIND) and TPPO ligands: the first X-ray structure of Eu–ACIND complex. Polyhedron. 2006; 25: 3488-3494.

6. Ahmedova A., Cador O., Sorace L., Ciattini S., Gatteschi D., Mitewa M. X-ray structure and magnetochemical study on a Co(II) complex of 2-acetyl-1,3-indandione. J. Coord. Chem. 2008; 61(24): 3879-3886.

7. Ahmedova A., Atanasov V., Marinova P., Stoyanov N., Mitewa M. Synthesis, characterization and spectroscopic properties of some 2-substituted 1,3-indandiones and their metal complexes. Cent. Eur. J. Chem. 2009; 7(3): 429-438.

8. Teotonio E.E.S., Brito H.F., Cremona M., Quirino W.G., Legnani C., Felinto M.C.F.C. Novel electroluminescent devices containing Eu3+-(2-acyl-1,3-indandionate) complexes with TPPO ligand. Opt. Mater. 2009; 32: 345-349.

9. Wang N., Tao X., Du F.-L., Feng M., Jiang M.-L., Shen Y.-Z. Synthesis and characterization of organophosphine/phosphite stabilized silver(I) complexes bearing 2-acetyl-1,3-indandione ligand, crystal structure of [Ph3P·AgC11H7O3]. Polyhedron. 2010; 29: 1687-1691.

10. Feng Y.-L. Synthesis and structure of bis(indene-1,2,3-trione-2-oximato)bis(aqua)Mn(II): Mn(C9H4NO3)2(H2O)2. Chinese J. Struct. Chem. 2003; 22(2): 133-136.

11. Butin K.P., Rakhimov R.D., Ilʹina I.G. Experimental and theoretical studies of anions of transition-metal chelate complexex in alkylation reactions at a metal atom. Russ. Chem. Bull. 1999; 48(1): 71-78.

12. Ahmedova A., Marinova P., Cattini S., Stoyanov N., Springborg M., Mitewa M. A combined experimental and theoretical approach for structural study on a new cinnamoyl derivative of 2-acetyl-1,3-indandione and its metal(II) complexes. Struct. Chem. 2009; 20: 101-111. doi:10.1007/s11224-008-9393-9.

13. Enchev V., Ahmedova A., Ivanova G., Wawer I., Stoyanov N., Mitewa M. Quantum chemical and spectroscopic study of the structure of 2-acetylindan-1,3-dione complexes with metal(II) ions. J. Molec. Struct. 2001; 595: 67-76.

14. Palkina K.K., Kochetov A.N. Synthesis and crystal structure of zinc(II) and manganese(II) complexes of 2-(diphenylacetyl)indandione-1,3. Rus. J. Inorg. Chem. 2010; 55(6): 889-894.

15. Kochetov A.N., Kuz'mina L.G. Copper(II) complex with 2-(diphenylacetyl)indanedione-1,3: synthesis and structure. Rus. J. Inorg. Chem. 2009; 54(2): 248-251.

16. Palkina K.K., Kochetov A.N., Savinkina E.V., Alikberova L.Yu. Synthesis and crystal structure of the Ag(I) complex with a cyclic β-diketone, 2-(diphenylacetyl)indan-1,3-dione (L), and the HL molecule. Rus. J. Inorg. Chem. 2006; 51(11): 1743-1749.

17. Wilkinson G. (ed.). Comprehensive coordination chemistry. V. 5. Late Transition Elements. Oxford: Pergamon press, 1987. 806 p.

18. Palkina K.K., Kochetov A.N. Crystal structure of [Cs2Na(H2O)2(C23H16O3)(C23H15O3)3]. Rus. J. Inorg. Chem. 2010; 55(7): 1037-1041.

19. Palkina K.K., Kochetov A.N. Synthesis and crystal structure of the potassium complex with 2-diphenylacetyl-1,3-indandione. Rus. J. Inorg. Chem. 2010; 55(8): 1216-1220.

20. Palkina K.K., Kochetov A.N. Synthesis and crystal structure of the potassium complex with 2-diphenylacetyl-1,3-indandione. Rus. J. Inorg. Chem. 2010; 55(8): 1216-1220.

21. Dolmella A., Gatto S., Girardi E., Bandoli G. X-ray structures of the anticoagulants coumatetralyl and chlorophacinone. Theoretical calculations and SAR investigations on thirteen anticoagulant rodenticides. J. Mol. Str. 1999; 513: 177-199.

22. Gromak V.V., Avakyan V.G., Pashkovskii F.S., Lakhvich O.F., Skorodumov E.V., Khlebnikova T.S.Analysis of the tautumeric properties of 2-formylcyclopentane-1,3-dione using the data of IR spectroscopy and nonempirical (ab initio and DFT) quantum-chemical calculations. J. Appl. Spectrosc. 2003; 70(1): 14-26.

23. Angelova S., Enchev V., Kostova K., Rogojerov M., Ivanova G. Theoretical and spectroscopic study of 2-substituted indan-1,3-diones: a coherent picture of the tautomeric equilibrium. J. Phys. Chem. A. 2007; 111(39): 9901-9913.

24. Ahmedova A., Pavlović G., Zhiryakova D., Šišak D., Stoyanov N., Springborg M., Mitewa M. Experimental and theoretical study on the structure and optical properties of 2-acyl-1,3-indandiones – conformational effects. J. Mol. Str. 2010; 981:10-20.

25. Enchev V., Monev V., Markova N., Rogozherov M., Angelova S., Spassova M. A model system with intramolecular hydrogen bonding: Effect of external electric field on the tautomeric conversion and electronic structures. Comput. Theor. Chem. 2013; 1006: 113-122.

26. Vaysberg A., Proskauer E., Riddik J., Tups E. Organic solvents. Physical properties and methods of purification. Moscow: Inostrannaya Literatura Publ., 1958. 518 p. (in Russ.)

27. Sheldrick G.M. Phase annealing in SHELX-90: direct methods for larger structures. Acta Crystallogr. A. 1990; 46: 467-473.

28. Sheldrick G.M. SHELXL93. Program for the refinement of crystal structures. Germany, University of Göttingen, 1997.

29. Kochetov A.N. Alikberova L.Yu., Savinkina E.V. The use of complex compounds of Cu(II) for the purification of industrially important 2-(acyl) indandione-1,3. Vestnik MITHT (Fine Chemical Technologies). 2007; 2(5): 57-59. (in Russ.)

30. Kochetov A.N. Alikberova L.Yu., Shestakov K.A. Metal complexes in the oxidation state (+2) 2-acyl derivatives of indandione-1,3. Vestnik MITHT (Fine Chemical Technologies). 2006; 1(6): 70-72. (in Russ.)

31. Lysenko K.A., Antipin M.Yu. Hydrogen bond in 3-acetyl-4-hydroxycoumarin: X-ray diffraction and quantum chemical calculations. Rus. Chem. Bull. 2001; 50(3): 400-412. (in Russ.).

32. Müller-Dethlefs K., Hobza P. Noncovalent interactions: a challenge for experiment and theory. Chem. Rev. 2000; 100: 143-167.

33. Cotton F., Wilkinson G. Fundamentals of inorganic chemistry. Moscow: Mir Publ., 1979. 485 p. (in Russ.).

34. Bowmaker G.A., Di Nicola C., Pettinari C., Skelton B.W., Somersc N., White A.H. Mechanochemical synthesis in copper(II) halide/pyridine systems: single crystal X-ray diffraction and IR spectroscopic studies. J. Chem. Soc. Dalton Trans. 2011; 40: 5102-5115.

35. Usova T.L., Osipov O.A., Minkina L.S., Zaletov V.G. Bis chelates of cobalt, copper, nickel, and zinc with 2-acetyl- and 2-benzoyl-1,3-indandione. Koordinatsionnaya khimiya. (Coordination Chemistry). 1983; 9(7): 879-881. (in Russ.).


Review

For citations:


Nosikova L.A., Kochetov A.N., Kudryashova Z.A., Tsivadze A.Yu. COMPETITION OF OXYGEN- AND NITROGEN-DONOR LIGANDS IN THE SYNTHESIS OF COMPLEX COMPOUNDS OF COPPER WITH 2-(PHENYL-4-CHLOROPHENYLACETYL)INDANDIONE-1,3. Fine Chemical Technologies. 2018;13(6):60-68. (In Russ.) https://doi.org/10.32362/2410-6593-2018-13-6-60-68

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