Abstract
Patterns of p-electron conjugation in cylindrical carbon nanostructures are studied. It is shown that the non-planar character of their carbon framework allows the formation of a conjugated system of р‑electrons different from a π-electron conjugated system. A fundamental characteristic of in-plane electron conjugation is the formation of a nodal lower bonding molecular orbital. It is established that the interaction between р-electrons in molecules with a nonplanar carbon framework produces unoccupied molecular orbitals that are characterized by specific localization of electron density and can participate in processes generated by external physical fields. Using the Hartree–Fock method with the 3-21G basis set and the DFTB3LYP theory with the 6-31G basis set, it is shown that in-plane conjugation, the value of which falls along with the dimension of carbon polygons, occurs between р-electrons in carbon nanorings with condensed 4-, 5-, and 6-membered rings.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
O. B. Tomilin, E. V. Rodionova, and E. A. Rodin, Russ. J. Phys. Chem. A 94, 1657 (2020).
E. A. Khakina, A. S. Peregudov, S. I. Troyanov, et al., Russ. Chem. Bull. 61, 264 (2012).
O. B. Tomilin, E. E. Muryumin, E. V. Rodionova, et al., Appl. Surf. Sci. 428, 171 (2018).
O. B. Tomilin, E. E. Muryumin, and E. V. Rodionova, Phys. Solid State 55, 2397 (2013).
J. Chandrasekhar, E. D. Jemmis, and P. v. R. Schleyer, Tetrahedron Lett. 39, 3707 (1979).
P. v. R. Schleyer, H. Jiao, M. N. Glukhovtsev, et al., J. Am. Chem. Soc. 116, 10129 (1994).
D. A. Bochvar and E. G. Gal’pern, Dokl. Akad. Nauk SSSR 209, 610 (1973).
T. G. Schmalz, W. A. Seitz, D. J. Klein, et al., Chem. Phys. Lett. 130, 203 (1986).
A. A. Fokin, H. Jiao, and P. v. R. Schleyer, J. Am. Chem. Soc. 120, 9364 (1998).
R. Herges, Chem. Rev. 106, 4820 (2006).
O. B. Tomilin, I. V. Stankevich, E. E. Muryumin, et al., Carbon 50, 5217 (2012).
M. W. Schmidt, K. K. Baldridge, J. A. Boatz, et al., J. Comput. Chem. 14, 1347 (1993).
R. M. Minyaev, V. I. Minkin, T. N. Gribanova, et al., Org. Chem. 68, 8588 (2003).
V. Zólyomi and J. Kürti, Phys. Rev. B 70, 085403 (2004).
O. Gülseren, T. Yildirim, and S. Ciraci, Phys. Rev. B 65, 153405 (2002).
A. Kleiner and S. Eggert, Phys. Rev. B 64, 113402 (2001).
T. J. Katz and N. Acton, J. Am. Chem. Soc. 95, 2738 (1973).
P. E. Eaton and T. W. Cole, J. Am. Chem. Soc. 86, 3157 (1964).
P. E. Eaton, Y. S. Or, and S. J. Branca, J. Am. Chem. Soc. 103, 2134 (1981).
M. M. Maslov, A. I. Podlivaev, and L. A. Openov, Phys. Solid State 53, 2532 (2011).
ACKNOWLEDGMENTS
The authors thank Professor A.V. Knyazev for participating in the discussion of our results.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated by E. Glushachenkova
Rights and permissions
About this article
Cite this article
Tomilin, O.B., Muryumin, E.E., Rodionova, E.V. et al. Patterns of р-Electrons Conjugation in Cylindrical Hydrocarbon Molecules. Russ. J. Phys. Chem. 96, 1506–1512 (2022). https://doi.org/10.1134/S0036024422070317
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036024422070317