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Open Chemistry

formerly Central European Journal of Chemistry


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Volume 7, Issue 3

Issues

Volume 13 (2015)

Synthesis, characterization and spectroscopic properties of some 2-substituted 1,3-indandiones and their metal complexes

Anife Ahmedova
  • Laboratory of Biocoordination and Bioanalytical Chemistry, Department of Chemistry, University of Sofia, 1164, Sofia, Bulgaria
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/ Vasil Atanasov
  • Laboratory of Biocoordination and Bioanalytical Chemistry, Department of Chemistry, University of Sofia, 1164, Sofia, Bulgaria
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/ Petja Marinova / Neyko Stoyanov / Mariana Mitewa
  • Laboratory of Biocoordination and Bioanalytical Chemistry, Department of Chemistry, University of Sofia, 1164, Sofia, Bulgaria
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Published Online: 2009-06-21 | DOI: https://doi.org/10.2478/s11532-009-0039-6

Abstract

New 2-acyl-1,3-indandione derivatives, compounds 1–4, were obtained by condensation of 2-acetyl-1,3-indandione with benzaldehyde, thiophene-2-aldehyde, thiophene-3-aldehyde and furane-2-aldehyde, respectively. The structures of the newly synthesized 2-substituted 1,3-indandiones were characterized by means of spectroscopic methods (FT-IR, 1H and 13C NMR, UV-Vis and MS). Based on the obtained results it is suggested that the compounds exist in the exocyclic enolic form. Mass spectral fragmentation paths are also proposed. In order to verify the possibility for tautomerization processes of the newly synthesized compounds their absorption spectra were recorded in various solvents. Furthermore, the complexation properties of the compounds with metal(II) ions were also studied. A series of non-charged complexes with Cu(II), Cd(II), Zn(II), Co(II) and Ni(II) was isolated and analyzed by elemental analyses and IR. The paramagnetic Cu(II) complexes were studied by EPR and distorted, flattened tetrahedral structures are predicted. The other metal complexes show the presence of water molecules, most probably coordinated to the metal ion, thus forming octahedral geometry. Ultimately, the studied properties of the newly synthesized compounds, 1–4, suggest that they may find application as extracting agents for metal ions, rather than as optical sensors.

Keywords: 1,3-indandiones; MS fragmentation; UV-Vis; Metal complexes; EPR

  • [1] E.I. Gudrinietse, J.J. Paulinsh, E.E. Liepinsh, A.F. Ievinsh, Dokl. Akad. Nauk SSSR 232, 1069 (1977) (in Russian) Google Scholar

  • [2] L.S. Geita, I.E. Dalberga, A.K. Grinvalde, E.E. Liepin, Zh. Org. Khim. 13, 1461 (1977) (in Russian) Google Scholar

  • [3] J. Amiel, J. Ploquin, L. Sparfel, G. Lebaut, R. Floch, Compt. Rend. Acad. Sci. Ser. C 288, 445 (1979) Google Scholar

  • [4] F.A.K. Amer, E.S. Afsah, H. Etman, Zeit. Naturf. Sect. B 34, 867 (1979) Google Scholar

  • [5] E.M. Afsah, M. Hammouda, M.M. Khalifa, Zeit. Naturf. Sect. B 45, 1055 (1990) Google Scholar

  • [6] V. Enchev, G. Ivanova, G. Pavlovic, M. Rogojerov, A. Ahmedova, M. Mitewa, J. Mol. Str. 654, 11 (2003) http://dx.doi.org/10.1016/S0022-2860(03)00175-3CrossrefGoogle Scholar

  • [7] S. Minchev, B.V. Aleksiev, Dokl. BAN 29, 527 (1976) (in Bulgarian) Google Scholar

  • [8] E.M. Afsah, H.M. Hassan, S.A. Elagizy, M.T. Zimaity, J. Prakt. Chem. 326, 841 (1984) http://dx.doi.org/10.1002/prac.19843260518CrossrefGoogle Scholar

  • [9] S.C. Piessard, J.M. Leger, G. Lebaut, J.C. Colleter, J.D. Brion, J. Chem. Res.-S 34 (1987) Google Scholar

  • [10] E.M. Afsah, M. Hammouda, H. Zoorob, M.M. Khalifa, M. Zimaity, Pharmazie 45, 255 (1990) Google Scholar

  • [11] G.R. Berezina, Y.G. Vorobev, R.P. Smirnov, Zh. Org. Khim. 35, 808 (1999) (in Russian) Google Scholar

  • [12] M.K. Bachlus, K.L. Menaria, Talanta 20, 420 (1973) http://dx.doi.org/10.1016/0039-9140(73)80173-0CrossrefGoogle Scholar

  • [13] J.M. Charlesworth, A.C. Partridge, Sens. Actuat. B-Chem. 3, 237 (1991) http://dx.doi.org/10.1016/0925-4005(91)80012-9CrossrefGoogle Scholar

  • [14] M.C. Mochon, J.A.M. Leyva, Microchem. J. 34, 83 (1986) http://dx.doi.org/10.1016/0026-265X(86)90105-0CrossrefGoogle Scholar

  • [15] Z.K. Si, W. Jiang, Y.J. Ding, J.T. Hu, Fresen. J. Anal. Chem. 360, 731 (1998) http://dx.doi.org/10.1007/s002160050793CrossrefGoogle Scholar

  • [16] M.A. Akl, Microchem. J. 75, 199 (2003) http://dx.doi.org/10.1016/S0026-265X(03)00097-3CrossrefGoogle Scholar

  • [17] E.E.S. Teotonio, H.F. Brito, H. Viertler, W.M. Faustino, O.L. Malta, G.F. de Sa, M.C.F.C. Felinto, R.H.A. Santos, M. Cremona, Polyhedron 25, 3488 (2006) http://dx.doi.org/10.1016/j.poly.2006.06.035CrossrefGoogle Scholar

  • [18] T. Eicher, R. Graf, G. Adiwidjaja, Tetrahedron 34, 1985 (1978) http://dx.doi.org/10.1016/0040-4020(78)80107-0CrossrefGoogle Scholar

  • [19] M.A. Morsi, A.M.A. Helmy, H.M. Fahmy, J. Electr. Chem. 148, 123 (1983) http://dx.doi.org/10.1016/S0022-0728(83)80135-1CrossrefGoogle Scholar

  • [20] M.A. Tovmasyan, I.V. Bulgarovskaya, V.M. Vozzhennikov, Zh. Fiz. Khim. 58, 1428 (1984) (in Russian) Google Scholar

  • [21] M.A. Tovmasyan I.V. Bulgarovskaya, V.M. Vozzhennikov, V.K. Belskii, Zh. Fiz. Khim. 58, 1437 (1984) (in Russian) Google Scholar

  • [22] P. Hrnciar, A. Gaplovsky, E. Jankulicova, J. Donovalova, Chem. Papers-Chem. Zvesti 42, 53 (1988) Google Scholar

  • [23] C. Bratschkov, S. Minchev, I. Schopov, Polymer 35, 1549 (1994) http://dx.doi.org/10.1016/0032-3861(94)90357-3CrossrefGoogle Scholar

  • [24] M. Utinans, O. Neilands, Adv. Mat. Opt. Electronics 9, 19 (1999) http://dx.doi.org/10.1002/(SICI)1099-0712(199901/02)9:1<19::AID-AMO360>3.0.CO;2-ICrossrefGoogle Scholar

  • [25] P.R. Bontchev, S. Minchev, M. Kashchieva, M. Mitewa, D. Mehandjiev, J. Prakt. Chem. 325, 803 (1983) http://dx.doi.org/10.1002/prac.19833250513CrossrefGoogle Scholar

  • [26] M. Mitewa, P.R. Bontchev, V. Enchev, S. Minchev, M. Kashchieva, J. Prakt. Chem. 327, 516 (1985) http://dx.doi.org/10.1002/prac.19853270318CrossrefGoogle Scholar

  • [27] S. Jursenas, V. Gulbinas, Z. Kuprionis, R. Kananavicius, G. Kodis, T. Gustavsson, J.C. Mialocq, L. Valkunas, Synth. Met. 109, 169 (2000) http://dx.doi.org/10.1016/S0379-6779(99)00222-2CrossrefGoogle Scholar

  • [28] S. Jursenas, V. Gulbinas, A. Gruodis, G. Kodis, V. Kovalevskij, L. Valkunas, Phys. Chem. Chem. Phys. 1, 1715 (1999) http://dx.doi.org/10.1039/a808611gCrossrefGoogle Scholar

  • [29] R. Karpicz, V. Getautis, K. Kazlauskas, S. Jursenas, V. Gulbinas, Chem. Phys. 351, 147 (2008) http://dx.doi.org/10.1016/j.chemphys.2008.05.001CrossrefGoogle Scholar

  • [30] S. Jursenas, A. Gruodis, G. Kodis, M. Chachisvilis, V. Gulbinas, E.A. Silinsh, J. Phys. Chem. B, 102, 1086 (1998) http://dx.doi.org/10.1021/jp971991eCrossrefGoogle Scholar

  • [31] S. Jursenas, A. Gruodis, G. Kodis, L. Valkunas, Adv. Mater. Opt. Electronics 6, 387 (1996) http://dx.doi.org/10.1002/(SICI)1099-0712(199609)6:5/6<387::AID-AMO263>3.0.CO;2-GCrossrefGoogle Scholar

  • [32] H. Schwartz, R. Mazor, V. Khodorkovsky, L. Shapiro, J.T. Klug, E. Kovalev, G. Meshulam, G. Berkovic, Z. Kotler, S. Efrima, J. Phys. Chem. B 105, 5914 (2001) http://dx.doi.org/10.1021/jp0038916CrossrefGoogle Scholar

  • [33] V. Enchev, S. Bakalova, G. Ivanova, N. Stoyanov, Chem. Phys. Lett. 314, 234 (1999) http://dx.doi.org/10.1016/S0009-2614(99)01160-4CrossrefGoogle Scholar

  • [34] V. Enchev, I. Abrahams, G. Ivanova, J. Mol. Struct. THEOCHEM 719, 169 (2005) http://dx.doi.org/10.1016/j.theochem.2005.01.030CrossrefGoogle Scholar

  • [35] A. Ahmedova, V. Mantareva, V. Enchev, M. Mitewa, Int. J. Cosm. Sci. 24, 103 (2002) http://dx.doi.org/10.1046/j.1467-2494.2002.00126.xCrossrefGoogle Scholar

  • [36] T.L. Usova, O.A. Osipov, L.S. Minkina, V.G. Zaletov, Koord. Khim. 9, 879 (1983) (in Russian) Google Scholar

  • [37] T.I. Tihvinskaya, V.E. Egert, G.P. Semenova, D.Ya. Yankovskaya, Izv. Acad. Nauk Latv. SSR, Ser. Khim. 220 (1979) (in Russian) Google Scholar

  • [38] D. Zacharova-Kalavska, A.I. Perjessy, Coll. Czech. Chem. Commun. 35, 225 (1970) CrossrefGoogle Scholar

  • [39] K.P. Butin, R. D. Rakhimov, I.G. Il’ina, Izv. Acad. Nauk, Ser. Khim. 71 (1999) (in Russian) Google Scholar

  • [40] V. Enchev, A. Ahmedova, G. Ivanova, I. Wawer, N. Stoyanov, M. Mitewa, J. Mol. Struct. 595, 67 (2001) http://dx.doi.org/10.1016/S0022-2860(01)00522-1CrossrefGoogle Scholar

  • [41] A. Ahmedova, V. Rusanov, A. Hazell, J. Wolny, G. Gochev, A.X. Trautwein, M. Mitewa, Inorg. Chim. Acta 359, 3123 (2006) http://dx.doi.org/10.1016/j.ica.2006.01.011CrossrefGoogle Scholar

  • [42] A. Ahmedova, O. Cador, L. Sorace, S. Ciattini, D. Gatteschi, M. Mitewa, J. Coord. Chem. 61, 3879 (2008) http://dx.doi.org/10.1080/00958970802187134CrossrefGoogle Scholar

  • [43] A. Ahmedova, P. Marinova, S. Ciattini, N. Stoyanov, M. Springborg, M. Mitewa, Struct. Chem. 20, 101 (2008) 438 http://dx.doi.org/10.1007/s11224-008-9393-9CrossrefGoogle Scholar

About the article

Published Online: 2009-06-21

Published in Print: 2009-09-01


Citation Information: Open Chemistry, Volume 7, Issue 3, Pages 429–438, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-009-0039-6.

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© 2009 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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