Study of Selected Spectral Properties and Complex Formation with Transition Metals Ions of a New Schiff’s Base Containing Fluorescein and Sulfamide Fragments

Abstract

A new azomethine based on N-aminofluorescein and ortho-tosylaminobenzaldehyde has been synthesized. Structure and properties of the obtained compound have been studied by means of IR, 1H NMR, and electron absorption spectroscopy as well as potentiometry. Using the DFT method, quantum-chemical simulation of electronic absorption spectra has been performed. The complexation of the obtained azomethine in solutions with Cu2+, Ni2+, and Co2+ cations has been studied. Metal chelates (1:2) with Cu(II), Ni(II), Zn(II), and Cd(II) have been isolated. Octahedral structure of the coordination site has been suggested for the obtained metal chelates.

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References

  1. 1.

    Formica, M., Fusi, V., Giorgi, L., and Micheloni, M., Coord. Chem. Rev., 2012, vol. 256, nos. 1–2, p. 170. https://doi.org/10.1016/j.ccr.2011.09.010

    CAS  Article  Google Scholar 

  2. 2.

    Hyman, L.M., Stephenson, C.J., Dickens, M.G., Shimizu, K.D., and Franz, K.J., Dalton Trans., 2010, vol. 39, no. 2, p. 568. https://doi.org/10.1039/B914568K

    CAS  Article  Google Scholar 

  3. 3.

    Li, T., Yang, Z., Li, Y., Liu, Z., Qi, G., and Wang, B., Dyes Pigm., 2011, vol. 88, no. 1, p. 103. https://doi.org/10.1016/j.dyepig.2010.05.008

    CAS  Article  Google Scholar 

  4. 4.

    Abebe, F.A. and Sinn, E., Tetrahedron Lett., 2011, vol. 52, no. 41, p. 5234. https://doi.org/10.1016/j.tetlet.2011.07.127

    CAS  Article  Google Scholar 

  5. 5.

    Fang-Jun., H., Yin C-A., Yang Y-T., Su, J., Chao J-B., and Liu D-S., Anal. Chem., 2012, vol. 84, no. 5, p. 2219. https://doi.org/10.1021/ac202734m

    Article  Google Scholar 

  6. 6.

    Goswami, S., Paul, S., and Manna, A., Tetrahedron Lett., 2014, vol. 55, no. 29, p. 3946. https://doi.org/10.1016/j.tetlet.2014.05.018

    CAS  Article  Google Scholar 

  7. 7.

    Yin, W., Zhu, H., and Wang, R., Dyes Pigm., 2014, vol. 107, p. 127. https://doi.org/10.1016/j.dyepig.2014.03.012

    CAS  Article  Google Scholar 

  8. 8.

    Abebe, F.A., Eribal, C.S., Ramakrishna, G., and Sinn, E., Tetrahedron Lett., 2011, vol. 52, no. 43, p. 5554. https://doi.org/10.1016/j.tetlet.2011.08.072

    CAS  Article  Google Scholar 

  9. 9.

    An, J-m., Yan, M-h., Yang, Z-y., Li, T-r., and Zhou, Q-x., Dyes Pigm., 2013, vol. 99, no. 1, p. 1. https://doi.org/10.1016/j.dyepig.2013.04.018

    CAS  Article  Google Scholar 

  10. 10.

    Popov, L.D., Tupolova, Yu.P., Askalepova, O.I., Shcherbakov, I.N., Levchenkov, S.I., Lukov, V.V., Kogan, V.A., Kaimakan, E.B., and Zubenko, A.A., Russ. J. Gen. Chem., 2010, vol. 80, no. 8, p. 1689. https://doi.org/10.1134/S1070363210080207

    CAS  Article  Google Scholar 

  11. 11.

    Lee, C., Yang, W., and Parr, R.G., Phys. Rev. (B), 1988, vol. 37, no. 2, p. 785. https://doi.org/10.1103/PhysRevB.37.785

    CAS  Article  Google Scholar 

  12. 12.

    Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648. https://doi.org/10.1063/1.464913

    CAS  Article  Google Scholar 

  13. 13.

    Ditchfield, R., Hehre, W.J., and Pople, J.A., J. Chem. Phys., 1971, vol. 54, no. 2, p. 724. https://doi.org/10.1063/1.1674902

    CAS  Article  Google Scholar 

  14. 14.

    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, VG., 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.J., Keith, 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., and Pople, J.A., Gaussian 03, Revision, A.1, Gaussian, Inc., Pittsburgh PA, USA, 2003.

    Google Scholar 

  15. 15.

    Diamond — Crystal and Molecular Structure Visualization Crystal Impact. http://www.crystalimpact.com/diamond.

  16. 16.

    Chemissian. http://www.chemissian.com.

  17. 17.

    Minkin, V.I., Tsukanov, A.V., Dubonosov, A.D., and Bren, V.A., Mol. Struct, 2011, vol. 998, no. 2, p. 179. https://doi.org/10.1016/j.molstruc.2011.05.029

    CAS  Article  Google Scholar 

  18. 18.

    Nolan, E.M. and Lippard, S.J., Acc. Chem. Res., 2009, vol. 42, no. 1, p. 193. https://doi.org/10.1021/ar8001409

    CAS  Article  Google Scholar 

  19. 19.

    Lever, A.B.P., Inorganic Electronic Spectroscopy, Amsterdam: Elsevier Sci. Publ., B.V., 1984, p. 250.

    Google Scholar 

  20. 20.

    Chen, X. and Ma, H., Anal. Chim. Acta, 2006, vol. 575, no. 2, p. 217. https://doi.org/10.1016/j.aca.2006.05.097

    CAS  Article  Google Scholar 

Download references

Funding

This study was performed in the scope of the internal grant of Southern Federal University (grant no. VnGr-07/2017-29) and supported by the Ministry of Science and Higher Education in the scope of the State Task to Federal Scientific Research Center “Crystallography and Photonics,” Russian Academy of Sciences (spectral studies). The study was performed using the equipment of the Center for Collective Usage “Molecular Spectroscopy” of Southern Federal University.

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Correspondence to L. D. Popov.

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No conflict of interest was declared by the authors.

Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 11, pp. 1747–1754.

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Popov, L.D., Borodkin, S.A., Askalepova, O.I. et al. Study of Selected Spectral Properties and Complex Formation with Transition Metals Ions of a New Schiff’s Base Containing Fluorescein and Sulfamide Fragments. Russ J Gen Chem 89, 2258–2263 (2019). https://doi.org/10.1134/S1070363219110161

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Keywords

  • azomethine
  • fluorescein
  • complexation in solutions
  • metal chelates