Exploration of tautomerizations of succinimide and maleimide assisted by ammonia and methanol: a theoretical perspective

  • Subhendu Sarkar
  • Tamalika Ash
  • Tanay Debnath
  • Abhijit K. DasEmail author
Regular Article


Tautomerizations of succinimide (2,5-pyrrolidinedione) and maleimide (2,5-pyrroledione) assisted by ammonia and methanol molecules have been studied at density functional theory level in aqueous medium implementing polarizable continuum model. Tautomerisms observed in succinimide are keto–enol and amine–imine, but maleimide shows only amine–imine tautomerization. The relative energies (Ers) of various species and activation energies (Eas) of the transition states involved in the tautomerization processes have been calculated and depicted in the potential energy surfaces. We have observed that with increasing the number of catalyst molecules from one to two, the barrier heights for the tautomeric conversions decrease.


Tautomerism Heterocyclic compounds Activation barrier PES DFT 



SS is grateful to University Grant Commission (UGC), Government of India, TA and TD are grateful to Council of Scientific and Industrial Research (CSIR), Government of India, for providing them research fellowships. The authors are thankful to the reviewer for his constructive comments and suggestions.

Compliance with ethical standards

Conflict of interest

The authors also declare no conflict of interest.


  1. 1.
    Valadbeigi Y, Farrokhpour H (2015) Struct Chem 26:539CrossRefGoogle Scholar
  2. 2.
    Kalia S, Sharma A, Kaith BS (2007) J Chem Sci 119:617CrossRefGoogle Scholar
  3. 3.
    Sarkar S, Ash T, Debnath T, Das AK (2018) Struct Chem 29:881CrossRefGoogle Scholar
  4. 4.
    Lledós A, Bertrán J (1981) Tetrahedron Lett 22:775CrossRefGoogle Scholar
  5. 5.
    Bertrán J, Lledós A, Revetllat JA (1983) Int J Quant Chem 23:587CrossRefGoogle Scholar
  6. 6.
    Zielinski TJ, Poirier RA, Peterson MR, Csizmadia IG (1983) J Comp Chem 4:419CrossRefGoogle Scholar
  7. 7.
    Li Q-G, Xue Y, Yan G-S (2008) J Mol Struct Theochem 868:55CrossRefGoogle Scholar
  8. 8.
    Martinez EV, Labbé AT (2010) J Comput Chem 31:2642CrossRefGoogle Scholar
  9. 9.
    Alagona G, Ghio C, Nagy PI (2010) Phys Chem Chem Phys 12:10173CrossRefPubMedGoogle Scholar
  10. 10.
    Shterev IG, Delchev VB (2009) Monatsh Chem 140:1381CrossRefGoogle Scholar
  11. 11.
    Chermhini AN, Farrokhpour H, Teimouri A, Pourmoghaddas F (2013) Struct Chem 24:1215CrossRefGoogle Scholar
  12. 12.
    Öğretir C, Aydemir S, Duran M, Kılıçkaya MS (2010) J Chem Eng Data 55:1477CrossRefGoogle Scholar
  13. 13.
    Öğretir C, Duran M, Aydemir S (2010) J Chem Eng Data 55:5634CrossRefGoogle Scholar
  14. 14.
    Wojnarowska Z, Wlodarczyk P, Kaminski K, Grzybowska K, Hawelek L, Paluch M (2010) J Chem Phys 133:094507CrossRefPubMedGoogle Scholar
  15. 15.
    Orabi EA (2018) RSC Adv 8:30842CrossRefGoogle Scholar
  16. 16.
    Singh V, Fedeles BI, Essigmann JM (2015) RNA 21:1CrossRefPubMedPubMedCentralGoogle Scholar
  17. 17.
    Ol’shevskaya IA, Pochinok VY, Avramenko LF (1971) Chem Heterol Compd 4:649CrossRefGoogle Scholar
  18. 18.
    Kaliman I, Nemukhin A, Varfolomeev S (2010) J Chem Theory Comput 6:184CrossRefPubMedGoogle Scholar
  19. 19.
    Takahashi O, Kobayashi K, Oda A (2010) Chem Biodivers 7:1349CrossRefPubMedGoogle Scholar
  20. 20.
    Aeberli P, Gogerty JH, Houlihan WJ, Iorio LC (1976) J Med Chem 19:436CrossRefPubMedGoogle Scholar
  21. 21.
    Corrêa R, Filho VC, Rosa PW, Pereira CI, Schlemper V, Nunes RJ (1997) Pharm Pharmacol Commun 3:67Google Scholar
  22. 22.
    Hall IH, Wong OT, Scovill JP (1995) Biomed Pharmacother 49:251CrossRefPubMedGoogle Scholar
  23. 23.
    Crider AM, Kolczynski TM, Yates KM (1980) J Med Chem 23:324CrossRefPubMedGoogle Scholar
  24. 24.
    Musso DL, Cochran FR, Kelley JL, McLean EW, Selph JL, Rigdon GC, Orr GF, Davis RG, Cooper BR, Styles VL, Thompson JB, Hall WR (2003) J Med Chem 46:399CrossRefPubMedGoogle Scholar
  25. 25.
    Zentz F, Valla A, Guillou RL, Labia R, Mathot A-G, Sirot D (2002) Farmaco 57:421CrossRefPubMedGoogle Scholar
  26. 26.
    Hazra BG, Pore VS, Dey SK, Datta S, Darokar MP, Saikia D, Khanuja SPS, Thakur AP (2004) Bioorg Med Chem Lett 14:773CrossRefPubMedGoogle Scholar
  27. 27.
    Kornet MJ, Crider AM, Magarian EO (1977) J Med Chem 20:1210CrossRefPubMedGoogle Scholar
  28. 28.
    Patsalos PN (2005) Epilepsia 46:140CrossRefPubMedGoogle Scholar
  29. 29.
    Aziz AA-MA (2007) Eur J Med Chem 42:614CrossRefPubMedGoogle Scholar
  30. 30.
    Hernández REJ, Miller PA, Miller MJ (2012) Med Chem Lett 3:799CrossRefGoogle Scholar
  31. 31.
    Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich A, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ (2016) Gaussian, Inc., Wallingford CTGoogle Scholar
  32. 32.
    Zhao Y, Truhlar DG (2008) Theor Chem Acc 120:215CrossRefGoogle Scholar
  33. 33.
    Tomasi J, Persico M (1994) Chem Rev 94:2027CrossRefGoogle Scholar
  34. 34.
    Cramer CJ, Truhlar DG (1999) Chem Rev 99:2161CrossRefPubMedGoogle Scholar
  35. 35.
    Miertuš S, Scrocco E, Tomasi J (1981) Chem Phys 55:117CrossRefGoogle Scholar
  36. 36.
    Tomasi J, Mennucci B, Cammi R (2005) Chem Rev 105:2999CrossRefPubMedGoogle Scholar
  37. 37.
    Ji P, Atherton J, Page MI (2012) Org Biomol Chem 10:5732CrossRefPubMedGoogle Scholar
  38. 38.
    Arslan NB, Özdemir N, Dayan O, Dege N, Koparir M, Koparir P, Muğlu H (2014) Chem Phys 439:1CrossRefGoogle Scholar
  39. 39.
    Arslan NB, Özdemir N (2015) J Mol Model 21:19CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Subhendu Sarkar
    • 1
  • Tamalika Ash
    • 1
  • Tanay Debnath
    • 1
  • Abhijit K. Das
    • 1
    Email author
  1. 1.School of Mathematical and Computational SciencesIndian Association for the Cultivation of ScienceJadavpur, KolkataIndia

Personalised recommendations