Abstract
The electronic structure of 1,4-cyclohexadiene for various angles between the double bond planes has been calculated by the AM1 method. The effects of through-bond and through-space interactions, which result in flattening and unflattening, respectively, are oppositely directed. These effects are specified for various bending angles. In addition to steric factors, electronic factors affect the conformational flexibility of 1,4-cyclohexadiene.
This is a preview of subscription content, log in via an institution to check access.
References
L. A. Carriera, R. O. Carter, and J. R. During,J. Chem. Phys., 1973,59, 812.
B. J. Monostori and A. Weber,J. Mol. Spectrosc., 1964,12, 129.
J. Laane and R. C. Lord,J. Mol. Spectrosc., 1971,39, 340.
K. B. Lipkowits, P. W. Rabideau, D. J. Raber, L. E. Hardee, P. V. R. Schleyer, A. J. Kos, and R. A. Kahn,J. Org. Chem., 1982,47, 1002.
V. G. Dashevskii, V. A. Naumov, and N. M. Zaripov,Zh. Strukt. Khim., 1970,11, 746 [J. Struct. Chem. USSR, 1970,11 (Engl. Transl.)].
R. Gleiter and W. Schafer,Acc. Chem. Res., 1990,23, 369.
R. Hoffmann,Acc. Chem. Res., 1971,4, 1.
P. P. Shorygin and A. N. Isaev,Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 307 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989,38, 260 (Engl. Transl.)].
V. I. Vovna,Elektronnaya struktura organicheskikh soedinenii [Electronic Structure of Organic Substances], Nauka, Moscow, 1991 (in Russian).
M. J. S. Dewar, E. G. Zoebich, and E. F. Healy,J. Am. Chem. Soc., 1985,107, 3902.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1676–1677, September, 1994.
Rights and permissions
About this article
Cite this article
Shishkin, O.V., Polyakova, A.S., Prezhdo, O.V. et al. Effect of electronic interactions between double bonds on the conformational flexibility of 1,4-cyclohexadiene. Russ Chem Bull 43, 1587–1588 (1994). https://doi.org/10.1007/BF00697157
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00697157