Skip to main content
SpringerLink
Log in

Structure and stabilization factors of the 2-aminobenzimidazolium–3,3′-(phenylmethylene)- bis(4-hydroxy-2H-chromen-2-one) anion associate in the system 4-hydroxy-2H-chromen-2-one–benzimidazol-2-amine–benzaldehyde

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

Abstract

The molecular and crystal structures of the ionic associate formed by 2-aminobenzimidazolium cation solvated by one dimethyl sulfoxide molecule and 3,3′-(phenylmethylene)bis(4-hydroxy-2H-chromen-2- one) anion were determined by X-ray analysis. This associate was isolated in the acid-catalyzed three-component reaction of 4-hydroxy-2H-chromen-2-one with benzimidazol-2-amine and benzaldehyde together with regioisomeric dihydrochromenopyrimidobenzimidazolones resulting from the classical Biginelli condensation. The steric and electronic structures of the cation and anion were calculated at the B3LYP/6-311++G(d,p) level of theory in combination with NBO analysis. Factors stabilizing the ion pair and crystal field effects on the stability of the associate and its constituents were considered. The formation of 3-[(2,4-dioxo-3H-chromen-3-yl)(phenyl)methyl]-2-oxo-2H-chromen-4-olate anion in the one-pot reaction was shown to be irreversible.

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. Hamdi, N., Lidrissi, C., Saoud, M., Romerosa Nievas, A., and Zarrouk, H., Chem. Heterocycl. Compd., 2006, vol. 42, p. 320.

    Article  CAS  Google Scholar 

  2. Parfenov, E. and Smirnov, L., Chem. Heterocycl. Compd., 1992, vol. 28, p. 274.

    Article  Google Scholar 

  3. Vasil’ev, S.A., Luk’yanchikov, M.S., Molchanov, G.I., Turubarov, V.D., and Khilya, V.P., Pharm. Chem. J., 1991, vol. 25, no. 7, p. 470.

    Article  Google Scholar 

  4. Jung, J.C., Lee, J.H., Oh, S., Lee, J.G., and Park, O.S., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 5527.

    Article  CAS  Google Scholar 

  5. Kostova, I., Curr. Med. Chem. Anti-Cancer Agents, 2005, vol. 5, p. 29.

    Article  CAS  Google Scholar 

  6. Chebanov, V.A. and Desenko, S.M., Mnogokomponentnye geterotsiklizatsii s upravlyaemoi selektivnost’yu. Reaktsii karbonil’nykh soedinenii s azotsoderzhashchimi mono-, bi-i polinukleofilami (Multicomponent Heterocyclizations with Controlled Selectivity, Reactions of Carbonyl Compounds with Nitrogen-Containing Mono-, Bi-, and Polynucleophiles), Saarbrücken: LAP LAMBERT, 2011.

    Google Scholar 

  7. Tietze, L.F., Brasche, G., and Gericke, K.M., Domino Reactions in Organic Synthesis, Weinheim, Wiley–VCH, 2006.

    Book  Google Scholar 

  8. Petrova, O.N., Zamigailo, L.L., Shirobokova, M.G., Shishkina, S.V., Shishkin, O.V., Musatov, V.I., and Lipson, V.V., Chem. Heterocycl. Compd., 2013, vol. 49, p. 955.

    Article  CAS  Google Scholar 

  9. Obaseki, A.O., Porter, W.R., and Steffen, J.E., J. Heterocycl. Chem., 1985, vol. 22, p. 529.

    Article  CAS  Google Scholar 

  10. Mazhukina, O.A., Platonova, A.G., Fedotova, O.V., and Vasin, V.A., Russ. J. Org. Chem., 2015, vol. 51, p. 691.

    Article  CAS  Google Scholar 

  11. Vdovina, S.V. and Mamedov, S.A., Russ. Chem. Rev., 2008, vol. 77, p. 1017.

    Article  CAS  Google Scholar 

  12. Gordon, A.J. and Ford, R.A., The Chemist’s Companion. A Handbook of Practical Data, Techniques, and References, New York: Wiley, 1972.

    Google Scholar 

  13. Agronomov, A.E., Izbrannye glavy organicheskoi khimii (Selected Topics of Organic Chemistry), Moscow: Khimiya, 1990.

    Google Scholar 

  14. Khachatryan, D.S. and Matevosyan, K.R., Russ. Chem. Bull., Int. Ed., 2016, vol. 65, p. 14.

    Google Scholar 

  15. Pimentel, G.C. and McClellan, A.L., The Hydrogen Bond, San Francisco: Freeman, 1960.

    Google Scholar 

  16. Castellano, R.K., Diederich, F., and Meyer, E.A., Angew. Chem., Int. Ed., 2003, vol. 42, p. 1210.

    Article  Google Scholar 

  17. Chumakov, Yu.M., Tsapkov, V.I., Bocelli, G., Antosyak, B.Ya., Palomares-Sánches, S.A., Ortiz, R.S., and Gulya, A.P., J. Struct. Chem., 2006, vol. 47, p. 923.

    Article  CAS  Google Scholar 

  18. Hunter, Ch.A., Kevin, R.L., Perkins, J., and Urc., Ch.J., J. Chem. Soc., Perkin Trans. 2, 2001, p. 651.

    Google Scholar 

  19. Hunter, C.A. and Sanders, J.-K.M., J. Am. Chem. Soc., 1990, vol. 112, p. 5525.

    Article  CAS  Google Scholar 

  20. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.

    Article  CAS  Google Scholar 

  21. Kohn, W., Rev. Mod. Phys., 1999, vol. 71, no. 5, p. 1253.

    Article  CAS  Google Scholar 

  22. 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 B.03, Wallingford CT: Gaussian, 2003.

    Google Scholar 

  23. Pankratov, A.N., Quantum Chemistry Research Trends, Kaisas, M.P., Ed., New York: Nova Science, 2007, p. 57.

  24. Becke, A.D., Phys. Rev. A, 1988, vol. 38, p. 3098.

    Article  CAS  Google Scholar 

  25. Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648.

    Article  CAS  Google Scholar 

  26. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, p. 785.

    Article  CAS  Google Scholar 

  27. Krishnan, R., Binkley, J.S., Seeger, R., and Pople, J.A., J. Chem. Phys., 1980, vol. 72, p. 650.

    Article  CAS  Google Scholar 

  28. McLean, A.D. and Chandler, G.S., J. Chem. Phys., 1980, vol. 72, p. 5639.

    Article  CAS  Google Scholar 

  29. Weinhold, F. and Landis, C.R., Valency and Bonding: A Natural Bond Orbital Donor–Acceptor Perspective, Cambridge, Cambridge Univ., 2005.

    Book  Google Scholar 

  30. Glendening, E.D., Reed, A.E., Carpenter, J.E., and Weinhold, F.A., NBO Version 3.1, 1995.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry, Chernyshevskii National Research Saratov State University, ul. Astrakhanskaya 83, Saratov, 410012, Russia

    A. N. Pankratov, O. V. Fedotova, A. G. Ozerova, O. A. Mazhukina & I. V. Strashilina

Authors
  1. A. N. Pankratov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. V. Fedotova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. G. Ozerova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. A. Mazhukina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. V. Strashilina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. N. Pankratov.

Additional information

Original Russian Text © A.N. Pankratov, O.V. Fedotova, A.G. Ozerova, O.A. Mazhukina, I.V. Strashilina, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 9, pp. 1338–1346.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pankratov, A.N., Fedotova, O.V., Ozerova, A.G. et al. Structure and stabilization factors of the 2-aminobenzimidazolium–3,3′-(phenylmethylene)- bis(4-hydroxy-2H-chromen-2-one) anion associate in the system 4-hydroxy-2H-chromen-2-one–benzimidazol-2-amine–benzaldehyde. Russ J Org Chem 52, 1326–1334 (2016). https://doi.org/10.1134/S107042801609013X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801609013X

Search

Navigation