Advertisement

Structural Chemistry

, Volume 25, Issue 2, pp 683–690 | Cite as

Tautomerism, structure in solution and in the solid state of 1:9,5:10-anthradipyrazole

  • Ibon Alkorta
  • José Elguero
Original Research

Abstract

By means of DFT calculations [B3LYP/6-311++G(d,p), GIAO], the properties of the three tautomers of 1:9,5:10-anthradipyrazole were analyzed and compared with Maspero’s crystal structures and NMR results. The agreement is fairly good and in agreement with indazole tautomers. Besides, the aromaticity of these interesting five-membered ring systems was explored.

Keywords

Anthradipyrazole Indazole Möhlau Tautomerism Aromaticity GIAO calculations 

Notes

Acknowledgments

Thanks are also given to the Ministerio de Economía y Competitividad of Spain (Project CTQ2012-13129-C02-02) and the Comunidad Autónoma de Madrid (Project MADRISOLAR2, ref. S2009/PPQ-1533). We thank Prof. Angelo Maspero for giving us the CIF of the structure of 1.

References

  1. 1.
    Möhlau R (1912) Ber Dtsch Chem Ges 45:2244CrossRefGoogle Scholar
  2. 2.
    Bradley W, Geddes KW (1952) J Chem Soc 1630Google Scholar
  3. 3.
    Maspero A, Giovenzana GB, Masciocchi N, Palmisano G, Comotti A, Sozzani P, Bassanetti I, Nardo L (2013) Cryst Growth Des 13:4948CrossRefGoogle Scholar
  4. 4.
    Becke AD (1988) Phys Rev A 38:3098CrossRefGoogle Scholar
  5. 5.
    Becke AD (1993) J Chem Phys 98:5648CrossRefGoogle Scholar
  6. 6.
    Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785CrossRefGoogle Scholar
  7. 7.
    Ditchfield R, Hehre WJ, Pople JA (1971) J Chem Phys 54:724CrossRefGoogle Scholar
  8. 8.
    Frisch MJ, Pople JA, Binkley JS (1984) J Chem Phys 80:3265CrossRefGoogle Scholar
  9. 9.
    Ditchfield R (1974) Mol Phys 27:789CrossRefGoogle Scholar
  10. 10.
    London F (1937) J Phys Radium 8:397CrossRefGoogle Scholar
  11. 11.
    Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, revision A.1. Gaussian, WallingfordGoogle Scholar
  12. 12.
    Silva AMS, Sousa RMS, Jimeno ML, Blanco F, Alkorta I, Elguero J (2008) Magn Reson Chem 46:859CrossRefGoogle Scholar
  13. 13.
    Blanco F, Alkorta I, Elguero J (2007) Magn Reson Chem 45:797CrossRefGoogle Scholar
  14. 14.
    Grimme S (2006) J Comp Chem 27:1787CrossRefGoogle Scholar
  15. 15.
    Boys SF, Bernardi F (1970) Mol Phys 19:553CrossRefGoogle Scholar
  16. 16.
    Alkorta I, Trujillo C, Elguero J, Solimannejad M (2011) Comput Theor Chem 967:147CrossRefGoogle Scholar
  17. 17.
    Bader RFW (1990) In: Halpen J, Green MLH (eds) Atoms in molecules: a quantum theory. The international series of monographs of chemistry. Clarendon, OxfordGoogle Scholar
  18. 18.
    Keith TA (2013) AIMAll (Version 13.10.19) TK Gristmill Software, Overland Park KS, USA. http://aim.tkgristmill.com. Accessed 4 July 2013
  19. 19.
    Escande E, Lapasset J, Faure R, Vincent EJ, Elguero J (1974) Tetrahedron 30:2903CrossRefGoogle Scholar
  20. 20.
    López C, Claramunt RM, Trofimenko S, Elguero J (1993) Can J Chem 71:678CrossRefGoogle Scholar
  21. 21.
    Elguero J, Fruchier A, Tjiou EM, Trofimenko S (1995) Chem Heterocyl Compd 1006Google Scholar
  22. 22.
    Catalán J, de Paz JLG, Elguero J (1996) J Chem Soc Perkin Trans 2:57CrossRefGoogle Scholar
  23. 23.
    García MA, López C, Claramunt RM, Kenz A, Pierrot M, Elguero J (2002) Helv Chim Acta 85:2763CrossRefGoogle Scholar
  24. 24.
    Alkorta I, Elguero J (2005) J Phys Org Chem 18:719CrossRefGoogle Scholar
  25. 25.
    Elguero J, Alkorta I, Claramunt RM, Cabildo P, Cornago P, Farrán MA, García MA, López C, Pérez-Torralba M, Santa María D, Sanz D (2013) Chem Heterocycl Compd 177Google Scholar
  26. 26.
    Alkorta I, Sánchez-Sanz G, Trujillo C, Elguero J, Claramunt RM (2012) ARKIVOC ii:85CrossRefGoogle Scholar
  27. 27.
    Alkorta I, Elguero J (1998) J Chem Soc Perkin Trans 2:2497CrossRefGoogle Scholar
  28. 28.
    Alkorta I, Blanco F, Elguero J (2008) Struct Chem 19:191CrossRefGoogle Scholar
  29. 29.
    Foces-Foces C (2005) Acta Crystallogr Sect E 61:o337CrossRefGoogle Scholar
  30. 30.
    González JLG, Ureña FP, Moreno JRA, Mata I, Molins E, Claramunt RM, López C, Alkorta I, Elguero J (2012) New J Chem 36:749CrossRefGoogle Scholar
  31. 31.
    Avilés Moreno JR, Quesada Moreno MM, López González JJ, Claramunt RM, López C, Alkorta I, Elguero J (2013) Chem Phys Chem 14:3355CrossRefGoogle Scholar
  32. 32.
    Pitonák M, Neogrády P, Rezác J, Jurecka P, Urban M, Hobza P (2008) J Chem Theor Comput 4:1829CrossRefGoogle Scholar
  33. 33.
    Gonzalez C, Lim EC (2003) J Phys Chem A 107:10105CrossRefGoogle Scholar
  34. 34.
    Elguero J, Fruchier A, Jacquier R, Scheidegger U (1971) J Chim Phys 68:1113Google Scholar
  35. 35.
    Fruchier A, Alcalde E, Elguero J (1977) Org Magn Reson 9:235CrossRefGoogle Scholar
  36. 36.
    Pinto J, Silva VLM, Silva AMS, Claramunt RM, Sanz D, Torralba MC, Torres MR, Reviriego F, Alkorta I, Elguero J (2013) Org Magn Reson 51:203Google Scholar
  37. 37.
    Schleyer PvR, Maerker C, Dransfeld A, Jiao H, Hommes NJRv (1996) J Am Chem Soc 118:6317CrossRefGoogle Scholar
  38. 38.
    Sánchez-Sanz G, Trujillo C, Rozas I, Elguero J (2013) Tetrahedron 69:7333CrossRefGoogle Scholar
  39. 39.
    Kruszewski J, Krygoeski TM (1972) Tetrahedron Lett 13:3839CrossRefGoogle Scholar
  40. 40.
    Zborowski KK, Alkorta I, Elguero J, Proniewicz LM (2013) Struct Chem 24:543CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.Instituto de Química Médica (C.S.I.C.)MadridSpain

Personalised recommendations