Abstract
The structure of perhydroacenaphthene (I) and its conversion products 1,3-dimethyladamantane (II), trans-1,4-dimethyladamantane (III), cis-1,4-dimethyladamantane (IV), 1,2-dimethyladamantane (V), 1-ethyladamantane (VI), and 2-ethyladamantane (VII) of the general formula C12H20 has been studied using the Becke-Lee-Yang-Parr (B3LYP) hybrid method for the energy functional of the electron density with the 6–31G* basis set. Geometric and electronic characteristics of the compounds and their total energy, trans-formation energies, transformation entropies, and normal vibration frequencies have been calculated. The equilibrium constants determined for the isomerization of perhydroacenaphthene into products II-VII are consistent with experimental data.
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References
E. I. Bagrii, Adamantanes: Synthesis, Properties, and Application (Nauka, Moscow, 1989) [in Russian].
Panorama of Modern Chemistry in Russia: Progress in Adamantane Chemistry, Ed. by N. S. Zefirov and I. K. Moiseev (Khimiya, Moscow, 2007) [in Russian].
E. I. Bagrii, R. E. Safir, and Yu. A. Arinicheva, Pet. Chem. 50, 1 (2010).
I. Hargittai and K. Hedberg, Molecular Structures and Vibrations, Ed. by S. J. Cyvin (Elsevier, Amsterdam, 1972), p. 340.
S. X. Tian, N. Kishimoto, and K. Ohno, J. Phys. Chem. A 106, 6541 (2002).
G. H. Kruppa and J. L. Beauchamp, J. Am. Chem. Soc. 108, 2126 (1985).
M. Kira, M. Akiyama, M. Ichinose, and H. Sakurai, J. Am. Chem. Soc. 111(21), 8256 (1989).
J. C. Rienstra-Kiracofe, G. S. Tschumper, and H. F. Schaefer, Chem. Rev. 102(1), 231 (2002).
E. I. Bagrii and P. I. Sanin, USSR Inventor’s Certificate No. 239302 (1971): Byull. Izobret., No. 25, 241 (1971).
E. I. Bagry and P. I. Sanin, US Patent No. 3637876 (1972).
E. I. Bagrii, P. I. Sanin, and T. N. Dolgopolova, Neftekhimiya 9, 353 (1969).
A. T. Saginaev, Novosti Nauki Kazakhstana, No. 1, 19 (2004).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian 98, Revision A.5 (Pittsburgh, 1998)
A. D. Becke, J. Chem. Phys. 98, 1372 (1993).
C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37, 785 (1988).
M. P. Tsyurupa, Yu. A. Borisov, Z. K. Blinnikiva, et al., Prot. Met. Phys. Chem. Surf. 50, 59 (2014).
D. A. McQuarrie, Statistical Thermodynamics (Harper and Row, New York, 1973).
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Original Russian Text © Yu.A. Borisov, A.T. Saginaev, 2014, published in Neftekhimiya, 2014, Vol. 54, No. 4, pp. 270–274.
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Borisov, Y.A., Saginaev, A.T. Calculation of geometric structure, electronic characteristics, vibration frequencies, and thermodynamic properties of C12H20 alkyladamantanes. Pet. Chem. 54, 270–274 (2014). https://doi.org/10.1134/S0965544114040021
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DOI: https://doi.org/10.1134/S0965544114040021