Skip to main content

Synthesis, Structural, and Physico-Chemical Study of Transition Metal Complexes with Schiff Base: A Product of Condensation of 2-N-Tosylaminobenzaldehyde and Tryptamine

Abstract

A new Schiff base, the product of 2-N-tosylaminobenzaldehyde and tryptamine condensation, was synthesized and investigated. A physicochemical study and quantum chemical simulation of the azomethinee tautomerism were performed. Its complexes with Zn(II), Cu(II), Ni(II), Co(II), and Fe(III) were synthesized and studied.

This is a preview of subscription content, access via your institution.

Scheme
Fig. 1.
Scheme
Fig. 2.
Fig. 3.

REFERENCES

  1. Minbaev, V.U., Shiffovy osnovaniya (Schiff Bases), Alma-Ata: Nauka, 1989.

  2. Garnovskii, A.D. and Vasil’chenko, I.S., Russ. Chem. Rev., 2002, vol. 71, no. 11, p. 943. https://doi.org/10.1070/RC2002v071n11ABEH000759

    CAS  Article  Google Scholar 

  3. Minkin, V.I., Tsukanov, A.V., Dubonosov, A.D., and Bren, V.A., J. Mol. Struсt., 2011, vol. 998, nos. 1–3, p. 179. https://doi.org/10.1016/j.molstruc.2011.05.029

    CAS  Article  Google Scholar 

  4. Segura, J.L., Mancheno, M.J., and Zamora, F., Chem. Soc. Rev., 2016, vol. 45, no. 20, p. 5635. https://doi.org/10.1039/C5CS00878F

    CAS  Article  PubMed  Google Scholar 

  5. Borisova, N.E., Reshetova, M.D., and Ustynyuk, Y.A., Chem. Rev., 2007, vol. 107, no. 1, p. 46. https://doi.org/10.1021/cr0683616

    CAS  Article  PubMed  Google Scholar 

  6. Garnovski, A.D., Nivorozhkin, A.L., and Minkin, V.I., Coord. Chem. Rev., 1993, vol. 126, nos. 11–12, p. 1. https://doi.org/10.1016/0010-8545(93)85032-Y

    Article  Google Scholar 

  7. Lukov, V.V., Kogan, V.A., Levchenkov, S.I., Shcherbakov, I.N., and Popov, L.D., Russ. J. Coord. Chem., 2015, vol. 41, no. 1, p. 1. https://doi.org/10.1134/S1070328415010054

    CAS  Article  Google Scholar 

  8. Lukov, V.V., Shcherbakov, I.N., Levchenkov, S.I., Popov, L.D., and Pankov, I.N., Russ. J. Coord. Chem., 2017, vol. 43, no. 1, p. 3. https://doi.org/10.1134/S1070328417010055

    CAS  Article  Google Scholar 

  9. Metelitsa, A.V., Burlov, A.S., Bezuglyi, S.O., Borodkina, I.G., Bren, V.A., Garnovskii, A.D., and Minkin, V.I., Russ. J. Coord. Chem., 2006, vol. 32, no. 12, p. 858. https://doi.org/10.1134/S1070328406120025

    CAS  Article  Google Scholar 

  10. Zhang, J., Xu, L, and Wong W.Y., Coord. Chem. Rev., 2018, vol. 355, p. 180. https://doi.org/10.1016/j.ccr.2017.08.007

    CAS  Article  Google Scholar 

  11. Kleij, A.W., Chem. Eur. J., 2008, vol. 14, no. 34, p. 10520. https://doi.org/10.1002/chem.200801149

    CAS  Article  PubMed  Google Scholar 

  12. Liu, X., Manzur, C., Novoa, N., Celedon, S., Carrillo, D., and Hamon, J.R., Coord. Chem. Rev., 2018, vol. 357, p. 144. https://doi.org/10.1016/j.ccr.2017.11.030

    CAS  Article  Google Scholar 

  13. Sarkar, S. and Dey, K., Spectrochim. Acta. (A), 2010, vol. 77, no. 4, p. 740. https://doi.org/10.1016/j.saa.2010.06.041

    CAS  Article  Google Scholar 

  14. Josephus, R.S. and Nair, M.S., Arab. J. Chem., 2009, vol. 62, p. 319. https://doi.org/10.1016/j.arabjc.2010.05.001

    CAS  Article  Google Scholar 

  15. Holm, R.H. and Solomon, E.I., Chem. Rev., 2004, vol. 104, no. 2, p. 347. https://doi.org/10.1021/cr0206364.

    CAS  Article  PubMed  Google Scholar 

  16. Da Silva, C.M., Da Silva, D.L., Modolo, L.V., Alves, R.B., De Resende, M.A., Martins, C.V.B., and De Fatima, A., J. Adv. Res., 2011, vol. 2, no. 1, p. 1. https://doi.org/10.1016/j.jare.2010.05.004

    Article  Google Scholar 

  17. Kovalenko, A., Rublev, P.O., Tcelykh, L.O., Goloveshkin, A.S., Lepnev, L.S., Burlov, A.S., Vashchenko, A.A., Marciniak, L., Magerramov, A.M., Shikhaliyev, N.G., Vatsadze, S.Z., and Utochnikova, V.V., Chem. Mater., 2019, vol. 31, no. 3, p. 759. https://doi.org/10.1021/acs.chemmater.8b03675

    CAS  Article  Google Scholar 

  18. Burlov, A.S., Koshchienko, Yu.V., Vlasenko, V.G., Dmitriev, A.V., Mal’tsev, E.I., Lypenko, D.A., Pozin, S.I., Levchenkov, S.I., Makarova, N.I., Tsivadze, A.Yu., and Minkin, V.I., Inorg. Chim. Acta, 2018, vol. 482, p. 863. https://doi.org/10.1016/j.ica.2018.07.037

    CAS  Article  Google Scholar 

  19. Burlov, A.S., Vlasenko, V.G., Koshchienko, Yu.V., Makarova, N.I., Zubenko, A.A., Drobin, Yu.D., Fetisov, L.N., Kolodina, A.A., Zubavichus, Ya.V., Trigub, A.L., Levchenkov, S.I., and Garnovskii, D.A., Polyhedron, 2018, vol. 154, p. 65. https://doi.org/10.1016/j.poly.2018.07.034

    CAS  Article  Google Scholar 

  20. Lifintseva, T.V., Burlo, A.S., Vlasenk, V.G., Koshchienko, Yu.V., Mal’tsev, E.I., Dmitriev, A.V., Lypenko, D.A., Trigub, A.L., and Garnovskii, D.A., Russ. J. Gen. Chem., 2018, vol. 88, no. 100, p. 2125. https://doi.org/10.1134/S107036321810016X

    CAS  Article  Google Scholar 

  21. Gili, P., Palacios, M.S., Martin-Reyes, M.G., Martin-Zarza, P., Ruiz-Perez, C., Rodriguez-Romero, F.V., and Lahoz, F.V., Polyhedron, 1992, vol. 11, no. 17, p. 2171. https://doi.org/10.1016/S0277-5387(00)83692-X

    CAS  Article  Google Scholar 

  22. Mustafa, I.M., Hapipah, M.A., Abdulla, M.A., and Ward, T.R., Polyhedron, 2009, vol. 28, no. 18, p. 3993. https://doi.org/10.1016/j.poly.2009.10.004

    CAS  Article  Google Scholar 

  23. Ali, H.M., Mustafa, M.I.M., Rizal, M.R., and Ng, S.W., Asta Cryst. E, 2008, vol. 64, no. 3, p. 787. https://doi.org/10.1107/S1600536808012968

    CAS  Article  Google Scholar 

  24. Ali, H.M., Mustafa, M.I.M., Rizal, M.R., and Ng, S.W., Acta Cryst. E, 2008, vol. 64, no. 2, p. 421. https://doi.org/10.1107/S1600536808002213

    CAS  Article  Google Scholar 

  25. Garcia-Raso, A., Fiol, J.J., Badenas, F., Lago, E., and Molins, E., Polyhedron, 2001, vol. 20, nos. 22-23, p. 2877. https://doi.org/10.1016/S0277-5387(01)00900-7

    CAS  Article  Google Scholar 

  26. Ishida, T., Hatta, K.I., Yamashita, S., Doi, M., and Iroue, M., Chem. Pharm. Bull., 1986, vol. 34, no. 9, p. 3553. https://doi.org/10.1248/cpb.34.3553

    CAS  Article  PubMed  Google Scholar 

  27. Gulli, P., Zarza, P.M., Nunez, P., Medina, A., Diaz, M.C., Martin, M.G., Arrieta, J.M., Vlassi, M., Germain, G., Vermeire, M., and Dupont, L., J. Coord. Chem., 1989, vol. 20, no. 3, p. 273. https://doi.org/10.1080/00958978909408169

    Article  Google Scholar 

  28. Yang, S., Zhu, X., Zhou, S., Wang, S., Feng, Z., Wei, Y., Miao, H., Guo, L., Wang, F., Zhang, G., Gu, X., and Mu, X., Dalton Trans., 2014, vol. 43, no. 6, p. 2521. https://doi.org/10.1039/C3DT51107C

    CAS  Article  PubMed  Google Scholar 

  29. Faizi, M.S.H., Sharkina, N.O., and Davydenko, Y.M., Acta Cryst. E, 2015, vol. 71, p. 31. https://doi.org/10.1107/S2056989015000778

    CAS  Article  Google Scholar 

  30. Liu, C., Niu, J.-F., Li, Y., Xu, J.-G., and Liu, X.-H., Chin. J. Struct. Chem., 2016, vol. 35, p. 1002. https://doi.org/10.14102/j.cnki.0254-5861.2011-1049

    CAS  Article  Google Scholar 

  31. Kahn, O., Molecular Magnetism, New York: VCH Publishers, 1993.

  32. Addison, A.W., Rao, N.T., Reedijk, J., Van Rijn, J., and Verschoor, G.C., J. Chem. Soc., Dalton Trans., 1984, no. 7, p. 1349. https://doi.org/10.1039/DT9840001349

    Article  Google Scholar 

  33. Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., and Puschmann, H., Acta Cryst. A, 2015, vol. 71, no. 1, p. 59. https://doi.org/10.1107/S2053273314022207

    CAS  Article  Google Scholar 

  34. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, no. 2, p. 339. https://doi.org/10.1107/S0021889808042726

    CAS  Article  Google Scholar 

  35. Sheldrick, G.M., Acta Cryst. A, 2008, vol. 64, no. 1, p. 112. https://doi.org/10.1107/S0108767307043930

    CAS  Article  Google Scholar 

  36. Spek, A.L., J. Appl. Cryst., 2003, vol. 36, p. 7. https://doi.org/10.1107/S0021889802022112

    CAS  Article  Google Scholar 

  37. 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., Bakken, V., 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.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 D.01. Gaussian, Inc., Wallingford CT, 2004.

  38. Zhurko, G.A. and Zhurko, G.A., Chemcraft ver. 1.6 (build 338). https://www.chemcraftprog.com.

  39. Cammi, R., Mennucci, B., and Tomasi, J., J. Phys. Chem. (A), 2000, vol. 104, no. 23, p. 5631. https://doi.org/10.1021/jp000156l

    CAS  Article  Google Scholar 

  40. Stephens, P.J., Devlin, F.J., Chabalowski, C.F., and Frisch, M.J., J. Phys. Chem., 1994, vol. 98, no. 45, p. 11623. https://doi.org/10.1021/j100096a001

    CAS  Article  Google Scholar 

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

    CAS  Article  Google Scholar 

  42. 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 

  43. Mahia, J., Maestro, M., Vazquez, M., Bermejo, M.R., Gonzalez, A.M., and Maneiro, M., Acta Crystallogr. (C), 1999, vol. 55, no. 12, p. 2158. https://doi.org/10.1107/S0108270199011580

    Article  Google Scholar 

Download references

Funding

The work was carried out with the financial support of the Southern Federal University.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to L. D. Popov.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Chetverikova, V.A., Popov, L.D., Levchenkov, S.I. et al. Synthesis, Structural, and Physico-Chemical Study of Transition Metal Complexes with Schiff Base: A Product of Condensation of 2-N-Tosylaminobenzaldehyde and Tryptamine. Russ J Gen Chem 90, 418–424 (2020). https://doi.org/10.1134/S1070363220030147

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363220030147

Keywords:

  • Schiff bases
  • X-ray diffraction
  • density functional theory
  • coordination compounds