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Tautomerization of pyrido[2′,1′:2,3]imidazo[4,5-B]quinoline-12-ylcyanide: A DFT study

  • Structure of Organic Compounds: Calculations and Experiments
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Abstract

The titled imidazo compound can exist as three tautomers: OH, CH, and NH forms. Firstly, the OH tautomer is produced, which can be tautomerized to the CH and NH tautomers via the intramolecularproton transfer. Herein, employing density functional theory and handling the solvent effects with the PCM model, the structural parameters, energy behavior, and also tautomerization mechanism of the tautomers are investigated. Based on the DFT results and the obtained-AIM parameters, the CH tautomer is considered to be the most stable one. Also, the CH tautomer is a kinetically and thermodynamically controlled product in tautomerization of the OH tautomer in a methanol solution.

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References

  1. H.-J. Knölker, R. Boese, and R. Hitzemann, Chem. Ber., 123, 327–329 (1990)and references therein.

    Article  Google Scholar 

  2. J. J. Kaminski, J. A. Bristol, C. Puchalski, R. G. Lovey, A. J. Elliott, H. Guzik, D. M. Solomon, D. J. Conn, M. S. Domalski, S. C. Wong, E. H. Gold, J. F. Long, J. S. Chiu, M. Steinberg, and A. T. McPhail, J. Med. Chem., 28, 876–892 (1985).

    Article  CAS  Google Scholar 

  3. J. J. Kaminski and A. M. Doweyko, J. Med. Chem., 40, 427–436 (1997).

    Article  CAS  Google Scholar 

  4. P. Sanfillipo, M. Urbanski, J. B. Press, B. Dubinsky, and J. B. Moore, J. Med. Chem., 31, 2221–2227 (1988).

    Article  Google Scholar 

  5. A. Gueiffier, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J. C. Teulade, A. Kerbal, E. M. Essassi, J. C. Debouzy, M. Witvrouw, Y. Blache, J. Balzarini, E. De Clercq, and J. P. Chapat, J. Med. Chem., 39, 2856–2859 (1996).

    Article  CAS  Google Scholar 

  6. A. Gueiffier, S. Mavel, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J. C. Teulade, M. Witvrouw, J. Balzarini, E. De Clercq, and J. P. Chapat, J. Med. Chem., 41, 5108–5112 (1998).

    Article  CAS  Google Scholar 

  7. M. Lhassani, O. Chavignon, J. M. Chezal, J. C. Teulade, J. P. Chapat, R. Snoeck, G. Andrei, J. Balzarini, E. De Clercq, and A. Gueiffier, Eur. J. Med. Chem., 34, 271–274 (1999).

    Article  CAS  Google Scholar 

  8. J. P. Kaplan and P. George, Chem. Abstr., 97, 149531a (1982).

  9. P. George, G. Rossey, M. Sevrin, S. Arbilla, H. Depoortere, and A. E. Wick, in: Imidazopyridines in Anxiety Disorders: A Novel Experimental and Therapeutic Approach, G. Bartholini, M. Garreau, P. L. Morselli, and B. Zivkovic (eds.), Raven Press, New York (1993). pp. 49–59.

  10. J. D. Hoehns and P. J. Perry, Clin. Pharmacol., 12, 814–828 (1993).

    CAS  Google Scholar 

  11. B. Edwin and I. H. Joe, J. Mol. Struct., 1034, 119–127 (2013).

    Article  CAS  Google Scholar 

  12. H. Eshtiagh-Hosseini, M. R. Housaindokht, S. A. Beyramabadi, S. Beheshti, A. A. Esmaeili, M. Javan-Khoshkholgh, A. Morsali, Spectrochim. Acta, Part A, 71, 1341–1347 (2008).

    Article  Google Scholar 

  13. S. A. Beyramabadi, A. Morsali, M. Javan-Khoshkholgh, and A. A. Esmaeili, Spectrochim. Acta, Part A, 83, 467–471 (2011).

    Article  CAS  Google Scholar 

  14. Z. Sadeghzade, S. A. Beyramabadi, and A. Morsali, Spectrochim. Acta, Part A, 138, 637–642 (2015).

    Article  CAS  Google Scholar 

  15. S. A. Beyramabadi, A. Morsali, S. H. Vahidi, M. Javan Khoshkholgh, and A. A. Esmaeili, J. Struct. Chem., 53, 665–675 (2012).

    Article  CAS  Google Scholar 

  16. H. Eshtiagh-Hosseini, S. A. Beyramabad, A. Morsali, M. Mirzaei, H. Chegini, M. Elahi, and M. A. Naseri, J. Mol. Struct., 1072, 187–194 (2014).

    Article  CAS  Google Scholar 

  17. S. H. Vahidi, A. Morsali, and S. A. Beyramabadi, Comput. Theor. Chem., 994, 41–46 (2012).

    Article  Google Scholar 

  18. S. A. Beyramabadi, H. Eshtiagh-Hosseini, M. R. Housaindokht, and A. Morsali, Organometallics, 27, 72–78 (2008).

    Article  CAS  Google Scholar 

  19. S. A. Beyramabadi, H. Eshtiagh-Hosseini, M. R. Housaindokht, and A. Morsali, J. Mol. Struct.: THEOCHEM, 903, 108–114 (2009).

    Article  CAS  Google Scholar 

  20. H. Eshtiagh-Hosseini, S. A. Beyramabadi, M. R. Housaindokht, and A. Morsali, J. Mol. Struct.: THEOCHEM, 941, 138–143 (2010).

    Article  CAS  Google Scholar 

  21. H. Eshtiagh-Hosseini, M. R. Housaindokht, S. A. Beyramabadi, S. H. Mir Tabatabaei, A. A. Esmaeili, and M. Javan- Khoshkholgh, Spectrochim. Acta, Part A, 78, 1046–1050 (2011).

    Article  Google Scholar 

  22. S. A. Beyramabadi, A. Morsali, M. Javan-Khoshkholgh, and A. A. Esmaeili, J. Struct. Chem., 53, 460–467 (2012).

    Article  CAS  Google Scholar 

  23. Y. L. Lin and J. Gao, Biochemistry, 49, 84–94 (2010).

    Article  CAS  Google Scholar 

  24. W. Rodríguez-Córdoba, J. S. Zugazagoitia, E. Collado-Fregoso, and J. Peon, J. Phys. Chem. A, 111, 6241–6247 (2007).

    Article  Google Scholar 

  25. M. Sauer, C. Yeung, J. H. Chong, B. O. Patrick, and M. J. MacLachlan, J. Org. Chem., 71, 775–788 (2006).

    Article  CAS  Google Scholar 

  26. A. Jezierska-Mazzarello, R. Vuilleumier, J. J. Panek, and G. Ciccotti, J. Phys. Chem. B, 114, 242–253 (2010).

    Article  CAS  Google Scholar 

  27. M. J. Frisch et al., Gaussian 03, Revision B.03, Gaussian Inc., Pittsburgh, PA (2003).

    Google Scholar 

  28. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, 785–789(1988).

    Article  CAS  Google Scholar 

  29. R. Cammi and J. Tomasi, J. Comput. Chem., 16, 1449–1458 (1995).

    Article  CAS  Google Scholar 

  30. M. Pordel, S. A. Beyramabadi, and A. Mohammadinejad, Dyes Pigm., 102, 46–52 (2014).

    Article  CAS  Google Scholar 

  31. X. Li, Y. Wang, S. Zheng, and L. Meng, Struct. Chem., 23, 1233–1240 (2012).

    Article  CAS  Google Scholar 

  32. H. Eshtiagh-Hosseini, S. A. Beyramabadi, A. Morsali, M. Mirzaei, H. Chegini, M. Elahi, and M. A. Naseri, J. Mol. Struct., 1072, 187–194 (2014).

    Article  CAS  Google Scholar 

  33. P. Gilli, V. Bertolasi, V. Ferretti, and G. Gilli, J. Am. Chem. Soc., 116, 909–915 (1994).

    Article  CAS  Google Scholar 

  34. S. Jenkins and I. Morrison, Chem. Phys. Lett., 317, 97–102 (2000).

    Article  CAS  Google Scholar 

  35. R. F. Bader, Atoms in Molecules: A Quantum Theory, Oxford University Press, Oxford (1990).

    Google Scholar 

  36. C. F. Matta, A. A. Arabi, and D. F. Weaver, Eur. J. Med. Chem., 45, 1868–1872 (2010).

    Article  CAS  Google Scholar 

  37. S. J. Grabowski and M. Malecka, J. Phys. Chem. A, 110, 11847–11854 (2006).

    Article  CAS  Google Scholar 

  38. R. N. Musin and Y. H. Mariam, J. Phys. Org. Chem., 19, 425–444 (2006).

    Article  CAS  Google Scholar 

  39. X. Fradera, M. A. Austen, and R. F. Bader, J. Phys. Chem. A, 103, 304–314 (1999).

    Article  CAS  Google Scholar 

  40. J. Poater, M. Sola, M. Duran, and X. Fradera, Theor. Chem. Acc., 107, 362–371 (2002).

    Article  CAS  Google Scholar 

  41. J. G. Angyan, M. Loos, and I. Mayer, J. Phys. Chem., 98, 5244–5248 (1994).

    Article  CAS  Google Scholar 

  42. Y. Mo and S. D. Peyerimhoff, J. Chem. Phys., 109, 1687–1697 (1998).

    Article  CAS  Google Scholar 

  43. R. F. Bader, M. T. Carroll, J. R. Cheeseman, and C. Chang, J. Am. Chem. Soc., 109, 7968–7979 (1987).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    S. A. Beyramabadi, A. Morsali, M. Pordel, H. Chegini, M. Khashi, I. Ahmadi & M. Poorzaki

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  1. S. A. Beyramabadi
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  2. A. Morsali
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  3. M. Pordel
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  4. H. Chegini
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  5. M. Khashi
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  6. I. Ahmadi
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  7. M. Poorzaki
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Correspondence to S. A. Beyramabadi.

Additional information

Original Russian Text © 2015 S. A. Beyramabadi, A. Morsali, M. Pordel, H. Chegini, M. Khashi, I. Ahmadi, M. Poorzaki.

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 56, No. 7, pp. 1318-1326, November-December, 2015.

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Beyramabadi, S.A., Morsali, A., Pordel, M. et al. Tautomerization of pyrido[2′,1′:2,3]imidazo[4,5-B]quinoline-12-ylcyanide: A DFT study. J Struct Chem 56, 1253–1261 (2015). https://doi.org/10.1134/S0022476615070045

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  • DOI: https://doi.org/10.1134/S0022476615070045

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