Skip to main content
SpringerLink
Log in

Polyynes vs. Cumulenes: Their Possible Use as Molecular Wires

  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

Polyynes and cumulenes from 2–12 atoms have been calculated at the B3LYP/6-311++G** level and their energies compared using an isodesmic reaction. The chain length has been modeled empirically affording an equation that predicts substantial variation for long chains.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Sacks, O. Oncle Tungsten, Memories of a Chemical Boyhood; Picador, 2001, p. 224.

  2. Greenwood, N. N., Earnshaw, A. Chemistry of Elements; Pergamon: Oxford, 1984.

    Google Scholar 

  3. Dresselhaus, M., Dresselhaus, G., Eklund, P. Science of Fullerenes and Carbon Nanotubes: Their Properties and Applications; Academic: New York, 1996; Kadish, K. M., Ruoff, R. S. Fullerenes: Chemistry, Physics, and Technology; Wiley-Interscience: New York, 2000.

  4. Merz, K. M., Hoffmann, R., Balaban, A. T. J. Am. Chem. Soc. 1987, 109, 6742–6751. Bucknum, M. J., Hoffmann, R. J. Am. Chem. Soc. 1994, 116, 11456–11464.

    Google Scholar 

  5. Johnston, R. L., Hoffmann, R. J. Am. Chem. Soc. 1989, 111, 810–819.

    Google Scholar 

  6. Karfunkel, H. R., Dressier, T. J. Am. Chem. Soc. 1992, 114, 2285–2288.

    Google Scholar 

  7. Balaban, A. T., Klein, D. J., Folden, C. A. Chem. Phys. Lett. 1993, 277, 266–270.

    Google Scholar 

  8. Kusner, R. B., Lahti, P. M., Lillya, C. P. Chem. Phys. Lett. 1995, 241, 522–527.

    Google Scholar 

  9. Narita, N., Nagai, S., Suzuki, S., Nakao, K. Phys. Rev. B: Condens. Matter Mater. Phys. 1998, 58, 11009–11014.

    Google Scholar 

  10. Fayos, J. J. Solid State Chem. 1999, 148, 278–285.

    Google Scholar 

  11. Heimann, R. B., Evsyukov, S. E., Kavan, L., Eds. Physics and Chemistry of Materials with Low-Dimensional Structures, Carbyne and Carbynoid Structures; Kluwer: Dordrecht, The Netherlands, 1999; Vol. 21.

    Google Scholar 

  12. Whittaker, A. G. Science 1978, 200, 763–764.

    Google Scholar 

  13. Diederich, R., Rubin, Y. Angew. Chem., Int. Ed. Engl. 1992, 31, 1101–1123.

    Google Scholar 

  14. Lagow, R. J., Kampa, J. J., Wei, H.-C., Battle, S. L., Genge, J. W., Laude, D. A., Harper, C. J., Bau, R., Stevens, R. C., Haw, J. R; Munson, E. Science 1995, 267, 362–367.

    Google Scholar 

  15. Lagow, R. J. (USA). PCT Int. Appl. WO 9622314 Al 25 Jul 1996, 36 pp. Chem. Abstr. 1996, 125, 196763.

  16. Bartik, T., Bartik, B., Brady, M., Dembinski, R., Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414–417.

    Google Scholar 

  17. Schermann, G., Grosser, T., Hampel, R., Hirsch, A. Chem.-Eur. J. 1997, 3, 1105–1112.

    Google Scholar 

  18. Elguero, J., Foces-Foces, C., Llamas-Saiz, A. L. Bull. Soc. Chim. Belg. 1992, 101, 795–799.

    Google Scholar 

  19. Kawai, T., Miyamoto, Y., Sugino, O., Koga, Y. Phys. Rev. B: Condens. Matter Mater. Phys. 2000, 62, R16349–R16352.

    Google Scholar 

  20. Diederich, F., Rubin, Y., Knobler, C., Whetten, R. L., Schriver, K. E., Houk, K. N., Li, Y. Science 1989, 245, 1088–1090.

    Google Scholar 

  21. Parasuk, V., Almlof, J., Feyereisen, M. W. J. Am. Chem. Soc. 1991, 113, 1049–1050.

    Google Scholar 

  22. Plattner, D. A., Houk, K. N. J. Am. Chem. Soc. 1995, 117, 4405–4406.

    Google Scholar 

  23. Martin, J. M. L., El-Yazal, J., Francois, J.-P. Chem. Phys. Lett. 1995, 242, 570–579.

    Google Scholar 

  24. Zahradnik, R., Hobza, P., Burcl, R., Andes Hess, B. Jr., Radziszewski, J. G. THEOCHEM 1994, 119, 335–349.

    Google Scholar 

  25. Mölder, U., Burk, P., Koppel, I. A. Int. J. Quant. Chem. 2001, 82, 73–85.

    Google Scholar 

  26. Horny, L., Petraco, N. D. K., Schaefer, H. F. III. J. Am. Chem. Soc. 2002, 124, 14716–14720.

    Google Scholar 

  27. Zahradnik, R., Sroubková, L. Helv. Chim. Acta 2003, 86, 979–1000.

    Google Scholar 

  28. Cataldo, F. Polym. Int. 1999, 44, 191–200.

    Google Scholar 

  29. Diederich, F., Martin, R. E. Angew. Chem. Int. Ed. 1999, 38, 1350–1377.

    Google Scholar 

  30. Mayor, M., Büschel, M., Fromm, K. M., Lehn, J.-M., Daub, J. Chem. Eur. J. 2001, 7, 1266–1272.

    Google Scholar 

  31. Utesh, N. F., Diederich, F. Org. Biomol. Chem. 2003, 1, 237–239.

    Google Scholar 

  32. Becke, A. D. J. Chem. Phys. 1993, 98, 5648–5652; Lee, C., Yang, W., Parr, R. G. Phys. Rev. B 1988, 37, 785–789.

  33. Ditchfield, R., Hehre, W. J., Pople, J. A. J. Chem. Phys. 1971, 54, 724–728; Frisch, M. J., Pople, J. A., Krishnam, R., Binkley, J. S. J. Chem. Phys. 1984, 80, 3265–3269.

    Google Scholar 

  34. Gaussian 98, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, Al-Laham, M. A., C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, Head-Gordon, M., E. S. Replogle, J. A. Pople, Eds., Gaussian Inc.: Pittsburgh, PA, 1998.

Download references

Author information

Authors and Affiliations

  1. Institute de Química Médica, CSIC, Juan de la Cierva, 3, E-28006, Madrid, Spain

    Ibon Alkorta & José Elguero

Authors
  1. Ibon Alkorta
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. José Elguero
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to José Elguero.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Alkorta, I., Elguero, J. Polyynes vs. Cumulenes: Their Possible Use as Molecular Wires. Struct Chem 16, 77–79 (2005). https://doi.org/10.1007/s11224-005-1089-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-005-1089-9

KEY WORDS:

Search

Navigation