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Journal of Structural Chemistry

, Volume 59, Issue 1, pp 43–46 | Cite as

A Quantum Chemical Study of the Acidity of Acetylene and 1,2-Dihydrobuckminsterfullerene Derivatives

  • M. V. Makarova
  • S. G. SemenovEmail author
  • R. R. Kostikov
Article
  • 43 Downloads

Abstract

DFT PBE0/cc-pVDZ method and the polarizable continuum model were used to determine pK a values for buckminsterfullerene-acetylene hybrids C60HCCH, C60HCN, tert-butylacetylene, and propyne relative to tert-BuC60H in a vacuum, carbon disulfide, tetrahydrofuran, and dimethyl sulfoxide. The energies of the СH-acid molecule and the carbanion (fulleride- or acetylide anion) were calculated using the same number of Gaussian orbitals. The surfaces of cavities formed by molecules and anions in a solvent are composed of spheres encompassing both atomic nuclei and lone electron pairs. An additional sphere excludes the solvent from the inner cavity of the fullerene.

Keywords

acetylenes fullerene CH-acid carbanion lone pair solvent effects DFT 

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References

  1. 1.
    M. V. Makarova, S. G. Semenov, and R. R. Kostikov, Russ. J. Org. Chem., 51, 273 (2015).CrossRefGoogle Scholar
  2. 2.
    K. Komatsu, N. Takimoto, Y. Murata, T. S. M. Wan, and T. Wong, Tetrahedron Lett., 37, 6153 (1996).CrossRefGoogle Scholar
  3. 3.
    P. Timmerman, H. L. Anderson, R. Faust, J.-F. Nierengarten, T. Habicher, P. Seiler, and F. Diederich, Tetrahedron, 52, 4925 (1996).CrossRefGoogle Scholar
  4. 4.
    M. Keshavarz-K, B. Knight, G. Srdanov, and F. Wudl, J. Am. Chem. Soc., 117, 11371 (1995).CrossRefGoogle Scholar
  5. 5.
    P. J. Fagan, P. J. Krusic, D. H. Evans, S. A. Lerke, and E. Johnston, J. Am. Chem. Soc., 114, 9697 (1992).CrossRefGoogle Scholar
  6. 6.
    I. V. Kuvychko, N. B. Shustova, S. M. Avdoshenko, A. A. Popov, S. H. Strauss, and O. V. Boltalina, Chem. Eur. J., 17, 8799 (2011).CrossRefGoogle Scholar
  7. 7.
    V. B. Luzhkov, Russ. Chem. Bull., 63, 561 (2014).CrossRefGoogle Scholar
  8. 8.
    V. B. Luzhkov, V. S. Romanova, and A. I. Kotelnikov, Russ. Chem. Bull., 63, 567 (2014).CrossRefGoogle Scholar
  9. 9.
    V. B. Luzhkov and A. I. Kotelnikov, Tetrahedron Lett., 56, 6008 (2015).CrossRefGoogle Scholar
  10. 10.
    J. Tomasi and M. Persico, Chem. Rev., 94, 2027 (1994).CrossRefGoogle Scholar
  11. 11.
    J. Tomasi, B. Mennucci, and R. Cammi, Chem. Rev., 105, 2999 (2005).CrossRefGoogle Scholar
  12. 12.
    S. G. Semenov and M. V. Makarova, Russ. J. Gen. Chem., 82, 1167 (2012).CrossRefGoogle Scholar
  13. 13.
    S. G. Semenov and M. V. Makarova, Opt. Spectrosc., 118, 46 (2015).CrossRefGoogle Scholar
  14. 14.
    M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian 09, Rev. C.01, Gaussian, Inc., Wallingford CT (2010).Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • M. V. Makarova
    • 1
  • S. G. Semenov
    • 1
    Email author
  • R. R. Kostikov
    • 1
  1. 1.Saint Petersburg State UniversityMoscowRussia

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