Structural Chemistry

, 17:13 | Cite as

Phosphole, pyrrole, and their tetrahydro derivatives: A theoretical study of their properties

Original Paper

Abstract

A theoretical analysis of four molecules (phosphole, phospholane, pyrrole, and pyrrolidine) in their ground and transition states has been carried out. The transition state of phosphole is highly aromatic and a partition of its energy into atomic contributions reveals that it is the phosphorus atom that is responsible for this observation.

Keywords

Phosphole Phospholane Pyrrole Pyrrolidine 

Notes

Acknowledgments

“MORPHY98, a program written by P.L.A. Popelier with a contribution from R.G.A. Bone, UMIST, Manchester, England, EU (1998).”.

References

  1. 1.
    Wittig G, Geissler G (1953) Liebigs Ann Chem 580:44CrossRefGoogle Scholar
  2. 2.
    Leavitt FC, Manuel TA, Johnson F (1959) J Am Chem Soc 81:3163CrossRefGoogle Scholar
  3. 3.
    Leavitt FC, Manuel TA, Johnson F, Matternas LU, Lehman DS (1960) J Am Chem Soc 82:5099CrossRefGoogle Scholar
  4. 4.
    Braye EH, Hübel W, Caplier I (1961) J Am Chem Soc 83:4406CrossRefGoogle Scholar
  5. 5.
    Mathey F (1980) Top Phosphorus Chem 10:1Google Scholar
  6. 6.
    Dimroth K (1984) Heterocyclic Rings containing Phosphorus. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry. Pergamon, Oxford, p 493Google Scholar
  7. 7.
    Mathey F (1988) Chem Rev 88:429CrossRefGoogle Scholar
  8. 8.
    Mathey F (1994) Phosphorus Sulfur 87:139CrossRefGoogle Scholar
  9. 9.
    Quin LD, Hughes AN (1990) In: Hartley FR (ed) The chemistry of organophosphorus compounds, vol. 1, ch. 10. Wiley, ChichesterGoogle Scholar
  10. 10.
    Hughes AN (1992) In: Engel R (ed) Handbook of organophosphorus chemistry, ch. 10. M. Dekker, New YorkGoogle Scholar
  11. 11.
    Quin LD (1996) Phospholes. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, p 757Google Scholar
  12. 12.
    Egan W, Tang R, Zon G, Mislow K (1970) J Am Chem Soc 92:1442CrossRefGoogle Scholar
  13. 13.
    Egan W, Tang R, Zon G, Mislow K (1971) J Am Chem Soc 93:6205CrossRefGoogle Scholar
  14. 14.
    Bodwell GJ, Bridson JN, Cyranski MK, Kennedy JWJ, Krygowski TM, Mannion MR, Miller DO (2003) J Org Chem 68:2089 and references cited thereinCrossRefGoogle Scholar
  15. 15.
    Hughes AN, Edgecombe KE (1992) Heterocycles 33:563CrossRefGoogle Scholar
  16. 16.
    Bachrach SM (1993) J Org Chem 58:5414CrossRefGoogle Scholar
  17. 17.
    Chesnut DB, Quin LD (1994) J Am Chem Soc 116:9638CrossRefGoogle Scholar
  18. 18.
    Nyulászi L (1996) J Phys Chem 100:6194CrossRefGoogle Scholar
  19. 19.
    Delaere D, Dransfeld A, Nguyen MT, Vanquickenborne LG (2000) J Org Chem 65:2631CrossRefGoogle Scholar
  20. 20.
    Nyulászi L (2000) Tetrahedron 56:79CrossRefGoogle Scholar
  21. 21.
    Pelzer S, Wichmann K, Wesendrup R, Schwerdtfeger P (2002) J Phys Chem (A) 106:6387CrossRefGoogle Scholar
  22. 22.
    Becke AD (1988) Phys Rev A 38:3098; Becke AD (1993) J Chem Phys 98:5648; Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785. Hariharan PA, Pople JA (1973) Theor Chim Acta 28:213Google Scholar
  23. 23.
    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 (2003) Gaussian 03, Gaussian, Inc., Pittsburgh, PAGoogle Scholar
  24. 24.
    Ditchfield R, Hehre WJ, Pople JA (1971) J Chem Phys 54:724CrossRefGoogle Scholar
  25. 25.
    Ditchfield R, Hehre WJ, Pople JA (1971) J Chem Phys 54:724. Frisch MJ, Pople JA, Krishnam R, Binkley JS (1984) J. Chem Phys 80:3265Google Scholar
  26. 26.
    Curtiss LA, Raghavachari K, Trucks GW, Pople JA (1991) J Chem Phys 94:7221. Curtiss LA, Raghavachari K, Trucks GW, Pople JA (1993) J Chem Phys 98:1293. Curtiss LA, Redfern PC, Smith BJ, Radom L (1996) J Chem Phys 104:5148Google Scholar
  27. 27.
    Bader RFW (1990) Atoms in molecules. A quantum theory. Oxford University, New YorkGoogle Scholar
  28. 28.
    “MORPHY98, a program written by P.L.A. Popelier with a contribution from R.G.A. Bone, UMIST, Manchester, England, EU (1998).“Google Scholar
  29. 29.
    Krygowski TM, Cyranski MK, Czarnocki Z, Hafelinger G, Katritzky AR (2000) Tetrahedron 56:1783CrossRefGoogle Scholar
  30. 30.
    Schleyer PVR, Jiao H (1996) Pure Appl Chem 68:209CrossRefGoogle Scholar
  31. 31.
    Bird CW (1985) Tetrahedron 41:1409CrossRefGoogle Scholar
  32. 32.
    Krygowski TM (1993) J Chem Inf Comput Sci 33:70Google Scholar
  33. 33.
    Krygowski TM, Cyranski MK (1996) Tetrahedron 52:10255CrossRefGoogle Scholar
  34. 34.
    Schleyer PVR, Maerker C, Dransfeld A, Jiao H, Eikema Hommes NJR (1996) J Am Chem Soc 118:6317CrossRefGoogle Scholar
  35. 35.
    Schleyer PVR, Monohar M, Wang Z, Kiran B, Jiao H, Puchta R, Hommes NJR (2001) Org Lett 3:2465CrossRefGoogle Scholar
  36. 36.
    Corminboeuf C, Heine T, Seifert G, Schleyer PVR, Weber J (2004) Phys Chem Chem Phys 6:273CrossRefGoogle Scholar
  37. 37.
    Cyranski M, Krygowski TM, Katritzky AR, Schleyer PVR (2002) J Org Chem 67:1333CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • Ibon Alkorta
    • 1
  • Krzysztof Zborowski
    • 1
    • 2
  • José Elguero
    • 1
  1. 1.Instituto de Química Médica (C.S.I.C.)MadridSpain
  2. 2.Faculty of ChemistryJagiellonian UniversityKrakówPoland

Personalised recommendations