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.
Similar content being viewed by others
REFERENCES
Minbaev, V.U., Shiffovy osnovaniya (Schiff Bases), Alma-Ata: Nauka, 1989.
Garnovskii, A.D. and Vasil’chenko, I.S., Russ. Chem. Rev., 2002, vol. 71, no. 11, p. 943. https://doi.org/10.1070/RC2002v071n11ABEH000759
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
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
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
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
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
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
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
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
Kleij, A.W., Chem. Eur. J., 2008, vol. 14, no. 34, p. 10520. https://doi.org/10.1002/chem.200801149
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
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
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
Holm, R.H. and Solomon, E.I., Chem. Rev., 2004, vol. 104, no. 2, p. 347. https://doi.org/10.1021/cr0206364.
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Kahn, O., Molecular Magnetism, New York: VCH Publishers, 1993.
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
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
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
Sheldrick, G.M., Acta Cryst. A, 2008, vol. 64, no. 1, p. 112. https://doi.org/10.1107/S0108767307043930
Spek, A.L., J. Appl. Cryst., 2003, vol. 36, p. 7. https://doi.org/10.1107/S0021889802022112
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.
Zhurko, G.A. and Zhurko, G.A., Chemcraft ver. 1.6 (build 338). https://www.chemcraftprog.com.
Cammi, R., Mennucci, B., and Tomasi, J., J. Phys. Chem. (A), 2000, vol. 104, no. 23, p. 5631. https://doi.org/10.1021/jp000156l
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
Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648. https://doi.org/10.1063/1.464913
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
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
Funding
The work was carried out with the financial support of the Southern Federal University.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363220030147