Skip to main content

Advertisement

Log in

Ferrocenoylhydrazone of 2-N-tosylaminobenzaldehyde: Structure, properties, and complexing ability

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

2-N-Tosylaminobenzaldehyde ferrocenoylhydrazone was synthesized. The crystal structure of the hydrazone was shown to include two independent molecules differing in mutual orientation of the tosyl and ferrocene fragments. Quantum-chemical simulation of the hydrazone tautomerism was performed. Its complexes with Cu(II), Ni(II), Zn(II), and Cd(II) were synthesized and investigated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Vigato, P.A. and Tamburini, S., Coord. Chem. Rev., 2004, vol. 248, nos. 18–20, pp. 1717. DOI: 10.1016/j.cct.2003.09.003.

    Article  CAS  Google Scholar 

  2. Vigato, P.A., Peruzzo, V., and Tamburini, S., Coord. Chem. Rev., 2012, vol. 56, nos. 11–12, pp. 953. DOI: 10.1016/j.ccr.2012.01.009.

    Article  Google Scholar 

  3. Popov, L.D., Morozov, A.N., Shcherbakov, I.N., Tupolova Yu.P., Lukov, V.V., and Kogan, V.A., Russ. Chem. Rev., 2009, vol. 78, no. 7, pp. 643. DOI: 10.1070/RC2009v078n07ABEH003890.

    Article  CAS  Google Scholar 

  4. Stadler, A.-M. and Harrowfield, J., Inorg. Chim. Acta, 2009, vol. 362, no. 12, pp. 4298. DOI: 10.1016/j.ica.2009.05.062.

    Article  CAS  Google Scholar 

  5. Fraga, C.A.M. and Barreiro, E.J., Curr. Med. Chem., 2006, vol. 13, no. 2, pp. 167. DOI: 10.2174/092986706775197881.

    Article  CAS  Google Scholar 

  6. Rollas, S. and Kücükgüzel, S.G., Molecules, 2007, vol. 12, no. 8, pp. 1910. DOI: 10.3390/12081910.

    Article  CAS  Google Scholar 

  7. Suvarapu, L.N., Seo, Y.K., Baek, S.O., and Ammireddy, V.R., Eur. J. Chem., 2012, vol. 9, no. 3, pp. 1288. DOI: 10.1155/2012/534617.

    CAS  Google Scholar 

  8. Parpiev, N.A., Yusupov, V.T., Yakimovich, S.N., and Sharipov Kh.G. Atsilgidrazony i ikh kompleksy s perekhodnymi metallami (Acetylhydrazones and Their Complexes with Transition Metals), Tasjkent: Fan, 1988.

    Google Scholar 

  9. Kogan, V.A., Zelentsov, V.V., Larin, G.M., and Lukov, V.V., Kompleksy perekhodnykh metallov s gidrazonami (Transition Metal Complexes with Hydrazones), Moscow: Nauka, 1990.

    Google Scholar 

  10. Millan, L., Fuentealba, M., Manzur, C., Carrillo, D., Faux, N., Caro, B., Robin-Le Guen, F., Sinbandhit, S., Ledoux-Rak, I., and Hamon, J.-R., Eur. J. Inorg. Chem., 2006, vol. 2006, no. 6, pp. 1131. DOI: 10.1002/ejic.200500955.

    Article  Google Scholar 

  11. Beer, P.D. and Sikanyika, H., Polyhedron, 1990, vol. 9, no. 8, pp. 1091. DOI: 10.1016/S0277-5387(00)81299-1.

    Article  CAS  Google Scholar 

  12. Choham, Z.H. and Praveen, M., Appl. Organomet. Chem., 2001, vol. 15, no. 7, pp. 617. DOI: 10.1002/aoc.179.

    Article  Google Scholar 

  13. Mahajan, A., Kremer, L., Louw, S., Guéradel, Y., Chibale, K., and Biot, C., Bioorg. Med. Chem. Lett., 2011, vol. 21, no. 10, pp. 2866. DOI: 10.1016/j.bmcl.2011.03.082.

    Article  CAS  Google Scholar 

  14. Maguene, G.M., Jakhlal, J., Ladyman, M., Vallin, A., Ralambomanana, D.A., Bousquet, T., Maugein, J., Lebibi, J., and Pélinski, L., Eur. J. Med. Chem., 2011, vol. 46, no. 1, pp. 31. DOI: 10.1016/j.ejmech.2010.10.004.

    Article  CAS  Google Scholar 

  15. Ornelas, C., New J. Chem., 2011, vol. 35, no. 10, pp. 1973. DOI: 10.1039/C1NJ20172G.

    Article  CAS  Google Scholar 

  16. Fang, C.-J., Duan, C.-Y., Mo, H., He, C., Meng, Q.-J., Liu, Y.-J., Mei, Y.-H., and Wang, Z.-M., Organometallics, 2001. Vol., 20, no. 12, pp. 2525. DOI: 10.1021/om000965r

  17. Ma, Y.-X., Lu, Z.-L., Song, Q.-B., and Wu, X.-L., J. Coord. Chem., 1994, vol. 32, no. 4, pp. 353. DOI: 10.1080/00958979408024255.

    Article  CAS  Google Scholar 

  18. Kamalendu, D. and Nandi, K.K., Synt. React. Inorg. Metal-Org. Chem., 1999, vol. 29, no. 3, pp. 419. DOI: 10.1080/00945719909349461.

    Article  Google Scholar 

  19. Lu, Z.-L., Xiao, W., Kang, B.-S., Su, C.-Y., and Liu, J., J. Mol. Struct., 2000, vol. 523, nos. 1–3, pp. 133. DOI: 10.1016/S0022-2860(99)00405-6.

    Article  CAS  Google Scholar 

  20. Taher, S.K., El-Sayed, M.A., Retatheba, M., and El-Dissouky, A., Synt. React. Inorg. Metal-Org. Chem., 2002, vol. 32, no. 10, pp. 1769. DOI: 10.1081/SIM-120016464.

    Article  Google Scholar 

  21. Liu, W.-Y., Ma, Y.-X., Juar, J.-F., and Wang, Y.-T., Synt. React. Inorg. Metal-Org. Chem., 2001, vol. 31, no. 5, pp. 917. DOI: 10.1081/SIM-100104859.

    Article  CAS  Google Scholar 

  22. Krishnamoorthy, P., Sathyadevi, P., Butorac, R.R., Cowley, A.H., Bhuvanesh, N.S.P., and Dharmaraj, N., Dalton Trans., 2012, vol. 41, no. 15, pp. 4423. DOI: 10.1039/c2dt11938b.

    Article  CAS  Google Scholar 

  23. Niu, Y., Zhang, H., Jia, H., Wu, Q., Li, F., and Zhang, H., Synth. React. Inorg. Metal-Org. Chem., 1997, vol. 27, no. 10, pp. 1491. DOI: 10.1080/00945719708003153.

    Article  CAS  Google Scholar 

  24. Huang, G.-S., Song, Q.-B., and Ma, Y.-X., Synt. React. Inorg. Metal-Org. Chem., 2001, vol. 31, no. 2, pp. 297. DOI: 10.1081/SIM-100002048.

    Article  CAS  Google Scholar 

  25. Yuan, Y., Cao, Z., Fu, N., Wang, J., Weng, L., Bezerra de Carvalho, A., and Peppe, C., J. Organomet. Chem., 2001, vols. 637–639, pp. 631. DOI: 10.1016/S0022-328X(01)00961-5

    Article  Google Scholar 

  26. Ma, Y.-X., Huang, G.-S., Jin, P., and Han, X.-J., Bull. Soc. Chim. Belg., 1991, vol. 100, no. 3, pp. 205. DOI: 10.1002/bscb.19911000306.

    CAS  Google Scholar 

  27. Wang, X., Han, X., Lu, W., Liu, X., and Sun, D., Synt. React. Inorg. Metal-Org. Chem., 1992, vol. 22, no. 8, pp. 1169. DOI: 10.1080/15533179208020260.

    Article  CAS  Google Scholar 

  28. Popp, F.D. and Moynahan, F.B., J. Heterocycl. Chem., 1970, vol. 7, no. 2, pp. 351. DOI: 10.1002/jhet.5570070216.

    Article  CAS  Google Scholar 

  29. Ma, Y., Li, F., and Sun, H., Inorg. Chim. Acta 1988, vol. 149, no. 2, pp. 209. DOI: 10.1016/S0020-1693(00) 86069-7.

    Article  CAS  Google Scholar 

  30. Li, W.-J., Song, M., and Xu, Y., Acta Cryst. Sect., E, 2011, vol. 68, pp. m8. DOI: 10.1107/S1600536811050835.

    Article  Google Scholar 

  31. Burlov, A.S., Kuznetsova, L.I., Adamova, S.I., Kurbatov, V.P., Bondarenko, G.I., and Garnovskii, A.D., Russ. J. Gen. Chem., 2000, vol. 70, no. 5, pp. 750.

    CAS  Google Scholar 

  32. Popov, L.D., Askalepova, O.I., Kaimakan, E.B., Tupolova Yu.P., Shcherbakov, I.N., Levchenkov, S.I., Lukov, V.V., Maevskii, O.V., Kogan, V.A., Burlov, A.S., and Zubenko, A.A., Russ. J. Gen. Chem., 2012, vol. 82, no. 7, pp. 1233. DOI: 10.1134/S1070363212070080.

    Article  CAS  Google Scholar 

  33. Popov, L.D., Shcherbakov, I.N., Levchenkov, S.I., Tupolova Yu.P., Burlov, A.S., Aleksandrov, G.G., Lukov, V.V., and Kogan, V.A., Russ. J. Coord. Chem., 2011, vol. 37, no. 6, pp. 483. DOI: 10.1134/S1070328411060078.

    Article  CAS  Google Scholar 

  34. Popov, L.D., Levchenkov, S.I., Shcherbakov, I.N., Tsaturyan, A.A., Tupolova Yu.P., Starikova, Z.A., Burlov, A.S., Lukov, V.V., and Kogan, V.A., Russ. J. Coord. Chem., 2013, vol. 39, no. 5, pp. 367. DOI: 10.1134/S107032841304009X.

    Article  CAS  Google Scholar 

  35. Raspopova, E.A., Popov, L.D., Morozov, A.N., Shcherbakov, I.N., Kogan, V.A., and Levchenkov, S.I., Russ. J. Gen. Chem., 2008, vol. 78, no. 8, pp. 1586. DOI: 10.1134/S1070363208080215.

    Article  CAS  Google Scholar 

  36. Raspopova, E.A., Morozov, A.N., Popov, L.D., Shcherbakov, I.N., Levchenkov, S.I., and Kogan, V.A., Russ. J. Gen. Chem., 2012, vol. 82, no. 1, pp. 131. DOI: 10.1134/S1070363212010215.

    Article  CAS  Google Scholar 

  37. Raspopova, E.A., Morozov, A.N., Bulanov, A.O., Popov, L.D., Shcherbakov, I.N., Levchenkov, S.I., and Kogan, V.A., Russ. J. Gen. Chem., 2012, vol. 82, no. 8, pp. 1457. DOI: 10.1134/S1070363212080233.

    Article  CAS  Google Scholar 

  38. Kitaev, Yu. and Buzykin, B.I., Gidrazony (Hydrazones), Moscow: Nauka, 1974.

    Google Scholar 

  39. Cammi, R., Mennucci, B., and Tomasi, J., J. Phys. Chem., A, 2000, vol. 104, no. 23, pp. 5631. DOI: 10.1021/jp000156l.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  41. Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, pp. 5648. DOI: 10.1063/1.464913.

    Article  CAS  Google Scholar 

  42. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, no. 2, pp. 785. DOI: 10.1103/PhysRevB.37.785.

    Article  CAS  Google Scholar 

  43. Osborne, A.G., Whitley, R.H., and Meads, R.E., J. Organomet. Chem., 1980, vol., 193, no. 3, pp. 345. DOI: 10.1016/S0022-328X(00)90295-X.

    Article  CAS  Google Scholar 

  44. Lauher, J.W. and Hoffman, R., J. Am.Chem. Soc., 1976, vol. 98, no. 7, pp. 1729. DOI: 10.1021/ja00423a017.

    Article  CAS  Google Scholar 

  45. Kahn, O., Molecular Magnetism, New York: Wiley-VCH Publishers, 1993.

    Google Scholar 

  46. Mahia, J., Maestro, M., Vazquez, M., Bermejo, M.R., Gonzalez, A.M., and Maneiro, M., Acta Crystallogr., C, 1999, vol. 55, no. 12, pp. 2158. DOI: 10.1107/S0108270199011580.

    Article  Google Scholar 

  47. 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.

    Google Scholar 

  48. Zhurko, G.A. and Zhurko, G.A., Chemcraft ver. 1.6 (build 338). URL: http://www.chemcraftprog.com.

  49. SMART and SAINT, Release 5.0, Area Detector control and Integration Software, Bruker AXS, Analytical X-Ray Instruments, Madison, Wisconsin, USA, 1998.

  50. Sheldrick, G.M., SADABS: A Program for Exploiting the Redundancy of Area-detector X-Ray Data, University of Göttingen, Göttingen, Germany, 1999.

    Google Scholar 

  51. Sheldrick, G.M., Acta Cryst. A, 2008, vol. 64, no. 1, pp. 112. DOI: 10.1107/S0108767307043930.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. I. Levchenkov.

Additional information

Original Russian Text © L.D. Popov, A.N. Morozov, E.A. Raspopova, S.I. Levchenkov, I.N. Shcherbakov, A.S. Burlov, G.G. Aleksandrov, V.A. Kogan, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 1, pp. 135–143.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Popov, L.D., Morozov, A.N., Raspopova, E.A. et al. Ferrocenoylhydrazone of 2-N-tosylaminobenzaldehyde: Structure, properties, and complexing ability. Russ J Gen Chem 85, 126–134 (2015). https://doi.org/10.1134/S1070363215010223

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215010223

Keywords

Navigation