Skip to main content
SpringerLink
Log in

Benzoid–Quinoid tautomerism of schiff bases and their structural analogs: LVII. 2-[(3-oxo-5-phenylpyrazolidin-1-yl)methylidene]-1H-indene-1,3(2H)-dione

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

Abstract

Potentially tautomeric azomethine imide, 2-[(3-oxo-5-phenylpyrazolidin-1-yl)methylidene]-1H-indene- 1,3(2H)-dione, has been synthesized by condensation of 5-phenylpyrazolidin-3-one with 2-(hydroxymethylidene)-1H-indene-1,3(2H)-dione. According to the IR, 1H and 13C NMR, and electronic absorption spectroscopy data and DFT B3LYP/6-311++G(d,p) quantum chemical calculations, the title compound in solution exists as planar tricarbonyl tautomer stabilized by intramolecular hydrogen bond between the NH proton of the pyrazolidine fragment and carbonyl oxygen atom of the indene fragment. Its crystal structure was determined by X-ray analysis.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Popova, O.S., Bren’, V.A., Tkachev, V.V., Utenyshev, A.N., Revinskii, Yu.V., Tikhomirova, K.S., Starikov, A.G., Borodkin, G.S., Dubonosov, A.D., Shilov, G.V., Aldoshin, S.M., and Minkin, V.I., Izv. Akad. Nauk, Ser. Khim., 2015, vol. 64, p. 648.

    Google Scholar 

  2. Shepelenko, E.N., Dubonosov, A.D., Bushkov, A.Ya., Sitkina, L.M., Bren’, V.A., Lyubarskaya, A.E., and Minkin, V.I., Zh. Org. Khim., 1990, vol. 26, p. 1540.

    CAS  Google Scholar 

  3. Chuev, I.I., Aldoshin, S.M., Kozina, O.A., Shepelenko, E.N., Bren’, V.A., and Minkin, V.I., Russ. Chem. Bull., 1992, vol. 41, p. 2230.

    Article  Google Scholar 

  4. Bren’, V.A., Ross. Khim. Zh., 1996, vol. 40, p. 134.

    Google Scholar 

  5. Minkin, V.I., Tsukanov, A.V., Dubonosov, A.D., and Bren, V.A., J. Mol. Struct., 2011, vol. 998, p. 179.

    Article  CAS  Google Scholar 

  6. Hashimoto, T., Kimura, H., Kavamata, Y., and Maruoka, K., Nat. Chem., 2011, vol. 3, p. 642.

    Article  CAS  Google Scholar 

  7. Wang, M., Huang, Z., Xu, J., and Robin Chi, Y., J. Am. Chem. Soc., 2014, vol. 136, p. 1214.

    Article  CAS  Google Scholar 

  8. Organic Photochromes, El’tsov, A.V., New York: Plenum, 1990, p. 257.

  9. Panfil, I., Urbanczyk-Lipkowska, Z., Suwinska, K., Solecka, J., and Chmielewski, M., Tetrahedron, 2002, vol. 58, p. 1199.

    Article  CAS  Google Scholar 

  10. Wolfbeis, O.S. and Junek, H., Z. Naturforsch., 1979, vol. 341, p. 283.

    Google Scholar 

  11. Gould, E., Lebl, T., Slawin, A.M.Z., Reid, M., and Smith, A.D., Tetrahedron, 2010, vol. 66, p. 8992.

    Article  CAS  Google Scholar 

  12. Koptelov, Yu.B., Sednev, M.V., and Kostikov, R.R., Russ. J. Org. Chem., 2012, vol. 48, p. 804.

    Article  CAS  Google Scholar 

  13. Geissler, G., Hippius, M., and Tomaschewski, G., J. Prakt. Chem., 1982, vol. 324, p. 903.

    Article  CAS  Google Scholar 

  14. Dudek, G.O., J. Am. Chem. Soc., 1963, vol. 85, p. 694.

    Article  CAS  Google Scholar 

  15. Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972. Translated under the title Sputnik khimika, Moscow: Mir, 1976, p. 128.

    Google Scholar 

  16. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., 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., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J. Gaussian 09, Revision D.01, Wallingford CT: Gaussian, 2013.

    Google Scholar 

  17. Barone, V. and Cossi, M., J. Phys. Chem. A, 1998, vol. 102, p. 1995.

    Article  CAS  Google Scholar 

  18. Sheldrick, G.M., SHELXTL v. 6.14, Structure Determination Software Suite, Madison, Wisconsin, USA: Bruker AXS, 2000.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Southern Federal University, pr. Stachki 194/2, Rostov-on-Don, 344090, Russia

    O. S. Popova, V. A. Bren’, K. S. Tikhomirova, G. S. Borodkin, I. E. Tolpygin & V. I. Minkin

  2. Institute of Chemical Physics Problems, Russian Academy of Sciences, Chernogolovka, Moscow oblast, Russia

    V. V. Tkachev, A. N. Utenyshev, G. V. Shilov & S. M. Aldoshin

  3. Southern Scientific Center, Russian Academy of Sciences, ul. Chekhova 41, Rostov-on-Don, 344006, Russia

    Yu. V. Revinskii, A. G. Starikov, A. D. Dubonosov & V. I. Minkin

Authors
  1. O. S. Popova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Bren’
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. V. Tkachev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. N. Utenyshev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yu. V. Revinskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. K. S. Tikhomirova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. A. G. Starikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. G. S. Borodkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. A. D. Dubonosov
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. I. E. Tolpygin
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. G. V. Shilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. S. M. Aldoshin
    View author publications

    You can also search for this author in PubMed Google Scholar

  13. V. I. Minkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Bren’.

Additional information

Original Russian Text © O.S. Popova, V.A. Bren’, V.V. Tkachev, A.N. Utenyshev, Yu.V. Revinskii, K.S. Tikhomirova, A.G. Starikov, G.S. Borodkin, A.D. Dubonosov, I.E. Tolpygin, G.V. Shilov, S.M. Aldoshin, V.I. Minkin, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 4, pp. 555–559.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Popova, O.S., Bren’, V.A., Tkachev, V.V. et al. Benzoid–Quinoid tautomerism of schiff bases and their structural analogs: LVII. 2-[(3-oxo-5-phenylpyrazolidin-1-yl)methylidene]-1H-indene-1,3(2H)-dione. Russ J Org Chem 52, 541–545 (2016). https://doi.org/10.1134/S1070428016040114

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428016040114

Keywords

Search

Navigation