Conclusions
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1.
The structure of eight monosubstituted and gem-disubstituted cyclopropanes and nine molecules of their linear analogs (2-substituted propanes) was calculated by a non-empirical method using the 3–21 GF basis set. It was shown that all the two-exponent basis sets describe the perturbation of the ring during substitution with identical accuracy.
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2.
The strain energy was calculated for the investigated cyclic compounds. It was shown that for the greater part the 3–21 and 4–31 GF basis sets give good agreement with experiment for this value.
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3.
A satisfactory linear relation was obtained between the degree of change in structure (the length of the bond opposite the substituent) and the stability (the strain energy) with the introduction of one or two gem-substituents into the cyclopropane molecule.
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Literature cited
R. R. Kostikov and A. F. Khlebnikov, Modern Problems of Organic Chemistry [in Russian], Vol. 7, Leningrad (1982), p. 36.
R. Fuchs, J. H. Hallman, and M. O. Perlman, Can. J. Chem.,60, 1832 (1982).
A. C. Hopkinson, M. A. McKinney, and M. H. Lien, J. Comp. Chem.,4, 513 (1983).
T. Clark, G. W. Spitznagel, R. Klose, et al., J. Am. Chem. Soc.,106, 4412 (1984).
D. Cremer and E. Kraka, J. Am. Chem. Soc.,107, 3811 (1985).
M. J. S. Dewar, Bull. Soc. Chim. Belg.,88, 957 (1980); J. Am. Chem. Soc.,106, 669 (1984).
C. Van Alsenoy, J. N. Scarsdale, and L. Schaefer, J. Chem. Phys.,74, 6278 (1981).
A. Skancke, Acta Chem. Scand.,37A, 337 (1983); J. Mol. Struct.,50, 173 (1978); J. Mol. Struct.,42, 232 (1977); Acta Chem. Scand.,36A, 637 (1982); J. Mol. Struct.,51, 267 (1979).
G. R. De Mare and M. R. Peterson, J. Mol. Struct.,89, 213 (1982); J. Mol. Struct.,104, 115 (1983).
H. Oberhammer and J. E. Boogs, J. Mol. Struct.,57, 157 (1979).
C. Gatti, M. Barzaghi, and M. Simonetta, J. Am. Chem. Soc.,107, 878 (1985).
L. Hedberg, K. Hedberg, and J. E. Boggs, J. Chem. Phys.,77, 2996 (1982).
J. D. Cox and G. Pilcher, Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York-London (1976).
I. F. Tupitsyn, A. Yu. Shibaev, and Yu. V. Puzanov, Teor. Éksp. Khim.,21, 399 (1985).
S. P. Zil'berg, A. I. Ioffe, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., (1982), p. 2481.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2769–2777, December, 1987.
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Puzanov, Y.V., Shibaev, A.Y. & Shlyapochnikov, V.A. Nonempirical quantum-chemical investigation of the effect of substituents on the structure of three-membered rings. 1. Monosubstituted and gem-disubstituted derivatives of cyclopropane. Russ Chem Bull 36, 2567–2574 (1987). https://doi.org/10.1007/BF00957236
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DOI: https://doi.org/10.1007/BF00957236