Conclusions
-
1.
The thermal effects of the reactions of complex formation and the dipole moments of complexes of AlBr3 with bromo-, methyl-, methoxy-, and phenoxy-substituted diphenyl ethers (DE) were measured. A correlation of the complex-forming ability of the DE with the Hammettσ-constants was established.
-
2.
The energies of pπ-conjugation of the investigated ethers were determined.
-
3.
The model D′, presupposing free but interrelated rotation of the phenyl rings around the C-O bond, is the most probable for substituted DE.
Similar content being viewed by others
Literature cited
I. P. Romm and E. N. Gur'yanova, Zh. Obshch. Khimii,38, 1297 (1968); I. P. Romm, E. N. Guryanova, and K. A. Kocheshkov, Tetrahedron,25, 2455 (1969).
I. P. Romm, V. V. Kopylov, and E. N. Gur'yanova, Zh. Struk. Khimii,11, 671 (1970).
V. V. Kopylov, I. P. Romm, E. N. Gur'yanova, and A. N. Pravednikov, Zh. Obshch. Khimii,44, 1980 (1974).
I. P. Gol'dshtein, E. N. Gur'yanova, and I. R. Karpovich, Zh. Fiz. Khimii,39, 932 (1965).
E. N. Gur'yanova and I. P. Gol'dshtein, Zh. Obshch. Khimii,32, 12 (1962).
Yu. A. Zhdanov and V. I. Minkin, Correlation Analysis in Organic Chemistry [in Russian], Izd. Rostovsk. Un-ta (1966), pp. 85, 192.
M. Gomel, M. Lumbroso, N. Marziano, and R. Passerini, Bull. Chim. France, 1908 (1959).
R. J. W. Le Fevre and J. D. Saxby, J. Chem. Soc., B, 1064 (1966).
I. A. Bogdanov and M. F. Vuks, Vestn. Leningr. Un-ta, Ser. Fiz. i Khim., No. 16, 46 (1965).
C. Garrigou-Lagrange, M. Horak, R. K. Khanna, and E. R. Lippincott, Collect. Czechoslov. Chem. Comm.,35, 3230 (1970).
K. Higasi, Dipole, Molecule, and Chemistry, Monograph Series of the Research Institute of Applied Electricity, Sapporo (1965), p. 13.
V. I. Minkin, O. A. Osipov, and Yu. A. Zhdanov, Dipole Moments in Organic Chemistry [in Russian], Khimiya, Leningrad (1968), pp. 79, 87.
O. A. Osipov, V. N. Minkin, and A. D. Garnovskii, Handbook of Dipole Moments [in Russian], Vysshaya Shkola (1971).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 828–834, April, 1975.
Rights and permissions
About this article
Cite this article
Romm, I.P., Kopylov, V.V., Gur'yanova, E.N. et al. Electron-donor properties and energy of pπ-conjugation of a series of substituted diphenyl ethers. Russ Chem Bull 24, 747–752 (1975). https://doi.org/10.1007/BF00920687
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00920687