Advertisement

Structural Chemistry

, Volume 24, Issue 6, pp 1829–1839 | Cite as

The structure and energetics of pyrrolidinones, tetrahydrofuranones, piperidinones, and tetrahydropyranones: a computational study

  • Margarida S. MirandaEmail author
  • Joaquim C. G. Esteves da Silva
  • Chi Hon
  • Steven J. McKerrall
  • Joel F. LiebmanEmail author
Original Research

Abstract

We have performed high level ab initio quantum chemical calculations for 2- and 3-pyrrolidinone; tetrahydro-2- and -3-furanone; 2-, 3-, and 4-piperidinone; and tetrahydro-2-, -3-, and -4-pyranone. The most stable molecular structures were obtained from DFT calculations using the B3LYP density functional and the 6-31G(d) and 6-311+G(3df,2p) basis sets. The respective enthalpies of formation have been computed by the G3(MP2)//B3LYP composite method and appropriately chosen reactions. The calculated results are in excellent agreement with experimental data reported in the literature.

Keywords

Pyrrolidinones and tetrahydrofuranones Piperidinones and tetrahydropyranones Heterocycles Structure and energetics Enthalpies of formation Computational 

Notes

Acknowledgments

M. S. Miranda thanks Fundação para a Ciência e a Tecnologia, FCT, Lisbon, Portugal, for the financial support under the frame of the Ciência 2008 program.

References

  1. 1.
    Ramachandran G, Karthikeyan NS, Giridharan P, Sathiyanarayanan KI (2012) Org Biomol Chem 10:5343CrossRefGoogle Scholar
  2. 2.
    Landenberger KB, Matzger AJ (2012) Cryst Growth Des 12:3603CrossRefGoogle Scholar
  3. 3.
    Baig GA (2012) J Chem Soc Pak 34:156Google Scholar
  4. 4.
    Adeosun CO, Samuel SO (2012) Adv Environ Biol 6:655Google Scholar
  5. 5.
    Yang C-P, Huang G-J, Huang H-C, Chen Y-C, Chang C-I, Wang S-Y, Chen I-S, Tseng Y-H, Chien S-C, Kuo Y-H (2012) Molecules 17:6585CrossRefGoogle Scholar
  6. 6.
    Wei LF, Yang H, Xie W, Zhao H, Yang SN, Yang HN, Zhao CP, Wang P, Xu SL, Miao JY, Zhao BX, Bi JZ (2012) J Alzheimer’s Dis 30:531Google Scholar
  7. 7.
    Wood WF, Brandes JA, Foy BD, Morgan CG, Mann TD, DeShazer DA (2012) Biochem Syst Ecol 43:51CrossRefGoogle Scholar
  8. 8.
    Gill SK, Xu H, Kirchhoff PD, Cierpicki T, Turbiak AJ, Wan B, Zhang N, Peng K-W, Franzblau SG, Garcia GA, Showalter HDH (2012) J Med Chem 55:3814CrossRefGoogle Scholar
  9. 9.
    van Noor PCM (2012) Chemosphere 87:125CrossRefGoogle Scholar
  10. 10.
    Bernard D, Zhao Y, Wang S (2012) J Med Chem 55:4934CrossRefGoogle Scholar
  11. 11.
    Powell NA, Kohrt JT, Filipski KJ, Kaufman M, Sheehan D, Edmunds JE, Delaney A, Wang Y, Bourbonais F, Lee D-Y, Schwende F, Sun F, McConnell P, Catana C, Chen H, Ohren J, Perrin LA (2012) Bioorg Med Chem Lett 22:190CrossRefGoogle Scholar
  12. 12.
    Wu P, Su Y, Liu X, Yang B, He Q, Hu Y (2012) Bioorg Med Chem 20:2837CrossRefGoogle Scholar
  13. 13.
    Wang J, Sun G, Li Z, Mai W, Xie J (2012) J Chem Res 36:63CrossRefGoogle Scholar
  14. 14.
    Makarov MV, Leonova ES, Rybalkina EY, Khrustalev VN, Shepel NE, Röschenthaler GV, Timofeeva TV, Odinets IL (2012) Arch Pharm 345:349CrossRefGoogle Scholar
  15. 15.
    Yang R, Wei B, Gao H, Yu W (2012) Sepu 30:160Google Scholar
  16. 16.
    Nottelet B, Patterer M, Francois B, Schott M-A, Domurado M, Garric X, Domurado D, Coudane J (2012) Biomacromolecules 13:1544CrossRefGoogle Scholar
  17. 17.
    Bruckner M, Westphal S, Domschke W, Kucharzik T, Lugering A (2012) J Crohns Colitis 6:226CrossRefGoogle Scholar
  18. 18.
    Cao P, Raleigh DP (2012) Biochemistry 51:2670CrossRefGoogle Scholar
  19. 19.
    Lemos LMS, Martins TB, Tanajura GH, Gazoni VF, Bonaldo J, Strada CL, da Silva MG, Dall’oglio EL, de Sousa PT Jr, de Oliveira MDT (2012) J Ethnopharmacol 141:432CrossRefGoogle Scholar
  20. 20.
    Kandhare AD, Raygude KS, Ghosh P, Ghule AE, Bodhankar SL (2012) Fitoterapia 83:650CrossRefGoogle Scholar
  21. 21.
    Baboul AG, Curtiss LA, Redfern PC, Raghavachari K (1999) J Chem Phys 110:7650CrossRefGoogle Scholar
  22. 22.
    Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, 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 JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03 Revision C.02. Gaussian, Inc, WallingfordGoogle Scholar
  23. 23.
    Ribeiro da Silva MAV, Cabral JITA, Gomes P, Gomes JRB (2006) J Org Chem 71:3677CrossRefGoogle Scholar
  24. 24.
    Liebman JF, Greenberg A (1974) Biophys Chem 1:222CrossRefGoogle Scholar
  25. 25.
    Pedley JB (1994) Thermochemical Data and Structures of Organic Compounds, vol 1. TRC Data Series, College StationGoogle Scholar
  26. 26.
    Ribeiro da Silva MAV, Ribeiro da Silva MDMC, Santos AFLOM, Roux MV, Foces-Foces C, Notario R, Guzman-Mejia R, Juaristi E (2010) J Phys Chem B 114:16471CrossRefGoogle Scholar
  27. 27.
    Adkins H, Elofson RM, Rossow AG, Robinson CC (1959) J Am Chem Soc 71:3622CrossRefGoogle Scholar
  28. 28.
    Roux MV, Notario R, Velez E, Temprado M, Guerrero A, Verevkin SP, Quijano J, Gaviria J (2007) J Chem Thermodyn 39:1377CrossRefGoogle Scholar
  29. 29.
    Yates WF, Heider RL (1952) J Am Chem Soc 74:4153CrossRefGoogle Scholar
  30. 30.
    Schlesinger G, Miller SL (1973) J Am Chem Soc 95:3729CrossRefGoogle Scholar
  31. 31.
    Bejaud M, Mion L, Commeyras A (1976) Bull Soc Chim Fr 233:1425Google Scholar
  32. 32.
    Verevkin SP, Beckhaus H-D, Rüchardt C (1995) Thermochim Acta 249:1CrossRefGoogle Scholar
  33. 33.
    Ribeiro da Silva MAV, Cabral JITA (2006) J Chem Eng Data 51:767CrossRefGoogle Scholar
  34. 34.
    Tewari YB, Vanderah DJ, Schantz MM, Goldberg RN, Rozzell JD, Liebman JF, Hui RW-M, Nissenbaum Y, Parniani AR (2008) J Chem Thermodyn 40:661CrossRefGoogle Scholar
  35. 35.
    Chase MW Jr (1998) J Phys Chem Ref Data Monogr 9:1Google Scholar
  36. 36.
    Ribeiro da Silva MAV, Cabral JITA (2006) J Chem Eng Data 51:1556CrossRefGoogle Scholar
  37. 37.
    Steele WV, Chirico RD, Nguyen A, Hossenlopp IA, Smith NK (1989) AIChE Symp Ser 85:140Google Scholar
  38. 38.
    Leitão MLP, Pilcher G, Meng-Yan Y, Brown JM, Conn AD (1990) J Chem Thermodyn 22:885CrossRefGoogle Scholar
  39. 39.
    Freitas VLS, Gomes JRB, Ribeiro da Silva MDMC (2009) J Therm Anal Calorim 97:827CrossRefGoogle Scholar
  40. 40.
    Greenberg A, Breneman CM, Liebman JF (eds) (2000), The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science (hardcover, 2000; amended paperback, 2003) Wiley, New YorkGoogle Scholar
  41. 41.
    Greenberg A, Liebman JF (1996) In: Martinho Simões JA, Greenberg A, Liebman JF (eds) Energetics of organic free radicals. Chapman and Hall, LondonGoogle Scholar
  42. 42.
    Greenberg A, Moore DT, DuBois TD (1996) J Am Chem Soc 118:8658CrossRefGoogle Scholar
  43. 43.
    Mucsi Z, Chass GA, Csizmadia IG (2008) J Phys Chem B 112:7885CrossRefGoogle Scholar
  44. 44.
    Glover SA, Rosser AA (2012) J Org Chem 77:5492CrossRefGoogle Scholar
  45. 45.
    Houk KN, Jabbari A, Hall HK, Aleman C (2008) J Org Chem 73:2674CrossRefGoogle Scholar
  46. 46.
    Leonard NJ, Oki M, Chiavarelli S (1955) J Am Chem Soc 77:6234CrossRefGoogle Scholar
  47. 47.
    Leonard NJ, Oki M, Brader J, Boaz H (1955) J Am Chem Soc 77:6237CrossRefGoogle Scholar
  48. 48.
    Spanka G, Rademacher P (1986) J Org Chem 51:592CrossRefGoogle Scholar
  49. 49.
    Spanka G, Rademacher P, Duddeck H (1988) J Chem Soc Perkin 2:2119Google Scholar
  50. 50.
    Wiberg KB, Waldron RF (1991) J Am Chem Soc 113:7697CrossRefGoogle Scholar
  51. 51.
    Wolf G (1972) Helv Chim Acta 55:1446CrossRefGoogle Scholar
  52. 52.
    Roux MV, Jiménez P, Dávalos JZ, Abboud J-LM, Molina MT (1996) J Chem Thermodyn 28:1029CrossRefGoogle Scholar
  53. 53.
    Jiménez P, Roux MV, Dávalos JZ, Martin-Luengo MA, Abboud J-LM (1997) J Chem Thermodyn 29:1281CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Margarida S. Miranda
    • 1
    Email author
  • Joaquim C. G. Esteves da Silva
    • 2
  • Chi Hon
    • 3
  • Steven J. McKerrall
    • 3
  • Joel F. Liebman
    • 3
    Email author
  1. 1.Centro de Geologia da Universidade do PortoPortoPortugal
  2. 2.Departamento de Química e BioquímicaCentro de Investigação em Química, Faculdade de Ciências da Universidade do PortoPortoPortugal
  3. 3.Department of Chemistry and BiochemistryUniversity of MarylandBaltimoreUSA

Personalised recommendations