Conclusions
-
1.
The13C NMR spectra of six 9-R-9,10-dimethylphenanthrenonium ions have been obtained for suppression of the {1H}-13C spin-spin bonding.
-
2.
The chemical shifts of the C10 atom (the carbonium center) of these ions are slightly sensitive to change in the substituent R.
-
3.
The value of the positive π charge at the carbonium center of the 9,9,10-trimethylphenanthrenonium ion (0.56 charge unit) has been estimated from the13C NMR spectra.
-
4.
The equilibrium concentration of ions of the phenonium type, which may participate as intermediate compounds in the degenerate regrouping of 9-X-phenyl-9,10-dimethylphenanthrenonium ions, does not exceed 3%
Similar content being viewed by others
Literature cited
V. G. Shubin, D. V. Korchagina, G. I. Borodkin, A. I. Rezvukhin, B. G. Derendyaev, and V. A. Koptyug, All-Union Conference on the Problem of Mechanisms of Heterolytic Reactions, Short Summaries [in Russian], Leningrad, Izd. Leningrad. Univ., 1974, p. 73.
J. B. Stothers, Carbon-13 NMR Spectroscopy, New York-London, Academic Press, 1972.
A. I. Rezvukhin, V. I. Mamatyuk, and V. A. Koptyug, Zh. Organ. Khim.,8, 2443 (1972).
V. I. Mamatyuk, A. I. Rezvukhin, A. N. Detsina, V. I. Buraev, I. S. Isaev, and V. A. Koptyug, Zh. Organ. Khim.,9, 2429 (1973).
A. I. Rezvukhin, V. N. Piottukh-Peletskii, R. N. Berezina, and V. G. Shubin, Izv. Akad. Nauk SSSR, Ser. Khim.,1973, 705.
V. G. Shubin, D. V. Korchagina, G. I. Borodkin, B. G. Derendyaev, and V. A. Koptyug, Zh. Organ. Khim.,9, 1031 (1973).
G. I. Borodkin, D. V. Korchagina, B. G. Derendjaev [Derendyaev], and V. G. Shubin, Tetrahedron Lett.,1973, 539.
V. G. Shubin, D. V. Korchagina, A. I. Rezvukhin, and V. A. Koptyug, Dokl. Akad. Nauk SSSR,179, 119 (1968).
V. G. Shubin, D. V. Korchagina, B. G. Derendyaev, G. I. Borodkin, and V. A. Koptyug, Zh. Organ, Khim.,9, 1041 (1973).
C. A. Coulson and A. Streitweiser, Jr., Dictionary of π-Electron Calculations, Pergamon Press, 1965, p. 198.
G. I. Borodkin, M. M. Shakirov, V. G. Shubin, and V. A. Koptyug, Zh. Organ. Khim.,10, 2622 (1974).
G. A. Olah and R. D. Porter, J. Am. Chem. Soc.,93, 6877 (1971).
V. A. Koptyug, É. T. Lippmaa, A. I. Rezvukhin, and T. I. Pekhk, Izv. Acad. Nauk SSSR, Ser. Khim.,1969, 185.
R. W. Rimmer, R. G. Christianser, R. K. Brown, and R. B. Sandin, J. Am. Chem. Soc.,72, 2298 (1950).
Author information
Authors and Affiliations
Additional information
See previous results in [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1253–1258, June, 1976.
Rights and permissions
About this article
Cite this article
Rezvukhin, A.I., Korchagina, D.V. & Shubin, V.G. Study of 9-R-9,10-dimethylphenanthrenonium ions by the method of nuclear magnetic resonance of carbon. Russ Chem Bull 25, 1213–1217 (1976). https://doi.org/10.1007/BF00928053
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00928053