Conclusions
-
1.
The parameters of the molecular ellipsoids of polarizability of p-chloro- and pbromotoluenes were determined. The additivity of the polarizability of toluenes methyland halosubstituted in the aromatic ring was confirmed.
-
2.
The parameters of the polarizability of the benzyl group in benzyl bromides were determined. Deviations of them from additivity as a result of interaction between the aromatic system and the bromine atom were detected.
-
3.
The conformation of benzyl bromides is characterized by shielding of the plane of the aromatic ring and one of the C-H bonds of the bromomethyl group.
-
4.
For orthosubstituted benzyl bromides only an antiorientation of the C-Br bond relative to the substituent is possible; metabromobenzyl bromide represents an equilibrium mixture of anti and syn forms in a 2:1 ratio.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
D. Stall, E. Westram, and G. Zinke, Chemical Thermodynamics of Organic Compounds [Russian translation], Mir (1971), p. 54.
M. T. Forel and M. Fourassier, Spectrochim. Acta,24A, 311 (1968).
R. J. W. Le Fevre, B. J. Orr, and G. L. D. Ritchie, J. Chem. Soc., 3619 (1965).
K. E. Calderbank, R. J. W. Le Fevre, and R. K. Pierens, J. Chem. Soc., B, 968 (1969).
K. E. Calderbank, R. J. W. Le Fevre, and R. K. Pierens, J. Chem. Soc., B, 1463 (1970).
R. J. W. Le Fevre and B. P. Rao, J. Chem. Soc., 3644 (1957).
Tables of Interatomic Distances and Configurations, London (1958).
O. A. Osipov, V. I. Minkin, and A. D. Garnovskii, Handbook of Dipole Moments [in Russian], Vysshaya Shkola (1971).
R. J. W. Le Fevre, Adv. Phys. Org. Chem.,3, 1 (1965).
M. J. Aroney, K. E. Calderbank, R. J. W. Le Fevre, and R. K. Pierens, J. Chem. Soc., B, 159 (1969).
K. E. Calderbank, R. J. W. Le Fevre, and R. K. Pierens, J. Chem. Soc., B, 968 (1969).
K. E. Calderbank, R. J. W. Le Fevre, and G. L. Ritchie, J. Chem. Soc., B, 503 (1968).
L. Verdonck and G. P. van der Kelen, Spectrochim. Acta,28A, 51, 55 (1972).
C. A. Cupas and J. M. Bollinger, J. Amer. Chem. Soc.,90, 5502 (1968).
W. Sheppard, Tetrahedron,27, 945 (1971).
S. G. Vul'fson, G. Ya. Cheryukanova, G. A. Chmutova, and A. N. Vereshchagin, Dokl. Akad. Nauk SSSR,212, 621 (1973).
R. L. Avoyan, Yu. T. Struchkov, and V. G. Dashevskii, Zh. Struktur. Khimii,7, 289 (1966).
C. G. Le Fevre and R. J. W. Le Fevre, Physical Methods of Organic Chemistry, Vol. 1, Part III, Interscience, New York (1960), p. 2459.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2474–2482, November, 1975.
Rights and permissions
About this article
Cite this article
Arbuzov, B.A., Vul'fson, S.G., Khamatullina, I.M. et al. Anisotropy of the polarizability and conformation of substituted benzyl bromides. Russ Chem Bull 24, 2361–2367 (1975). https://doi.org/10.1007/BF00921648
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00921648