Conclusions
-
1.
The dissociation constants of p-, m-, and o-ferrocenylbenzoic acids, ferrocenecarboxylic acid, and p-ferrocenylphenol were determined, along with the basicity constants of p-, m-, and o-ferrocenylanilines and ferrocenylamine.
-
2.
The values of the σ constants for ferrocenyl as a substituent in the phenyl ring were calculated.
-
3.
The nature of certain electronic effects of ferrocenyl as a substituent was studied. Ferrocenyl exhibits a strong positive inductive effect and a weak positive conjugation effect.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
L. P. Hammett, Chem. Revs.17, 125 (1935).
H. Van Bekkum, P. E. Verkade, and B. M. Wepster, Rec. Trav. Chem. Pays-Bas,78, 815 (1959).
R. W. Taft Jr., J. Amer. Chem. Soc.,79, 1045 (1957).
R. W. Taft. Jr., and J. R. Lewis, J. Amer. Chem. Soc.,80, 2436 (1958).
N. N. Lichtin and H. P. Leftin, J. Amer. Chem. Soc.,74, 4207 (1952).
J. D. Roberts, E. A. McElhill, and R. Armstrong, J. Amer. Chem. Soc.,71, 2923 (1949).
J. D. Roberts, R. L. Webb, and E. A. McElhill, J. Amer. Chem. Soc.,72, 408 (1950).
W. F. Little, R. A. Berry, and P. Kannan, J. Amer. Chem. Soc.,84, 2525 (1962).
E. M. Arnett and R. D. Bushik, J. Organ. Chem.,27, III (1962).
A. N. Nesmeyanov, É. G. Perevalova, and R. V. Golovnya, Dokl. AN SSSR,99, 539 (1954).
A. N. Nesmeyanov, É. G. Perevalova, R. V. Golovnya, and L. S. Shilovtseva, Dokl. AN SSSR,102, 535 (1955).
G. D. Broadhead and P. L. Pauson, J. Chem. Soc.,1955, 367.
A. N. Nesmeyanov, Substitution im Ferrozen-Kern, Referatenband XIV Internationaler Kongress für reine und angewandte Chemie, Zürich,1955, p. 193.
A. N. Nesmeyanov, É. G. Perevalova, L. P. Yur'eva, and K. I. Grandberg, Izv. AN SSSR, Ser. Khim.,1963, 1377.
J. K. Lindsay and C. R. Hauser, J. Organ. Chem.22, 355 (1957).
B. S. Kikot', Zh. Obshch. Khimii,33, 227 (1963).
H. H. Jaffe, Chem. Revs.53, 191 (1953).
S. P. Gubin and É. G. Perevalova, Dokl. AN SSSR,143, 1351 (1962).
É. G. Perevalova, S. P. Gubin, S. A. Smirnova, and A. N. Nesmeyanov, Dokl. AN SSSR,147, 384 (1962).
D. H. McDaniel and H. C. Brown, J. Organ. Chem.,23, 420 (1958).
A. N. Nesmeyanov, É. G. Perevalova, and R. V. Golovnya, Dokl. AN SSSR,103, 81 (1955).
V. A. Pal'm, Uspekhi Khimii,30, 1069 (1961).
O. Éksner, Transactions of the Conference on Problems of the Use of Correlational Equations of Organic Chemistry [in Russian], Tartu, EstSSR (1963), Vol. 1, p. 67.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 832–839, May, 1966.
Rights and permissions
About this article
Cite this article
Perevalova, É.G., Grendberg, K.I., Zharikova, N.A. et al. Electronic influence of ferrocenyl as a substituent. Russ Chem Bull 15, 796–802 (1966). https://doi.org/10.1007/BF00849374
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00849374