Abstract
The solvent and polymer matrix effects on the conformation equilibrium in 1,1,2,2-tetrabromoethane (TBE) are investigated by IR spectroscopy. The free energy differences (ΔG0) of TBE conformations correlate with the dielectric permittivity function of the medium. A pronounced solvent effect on the absolute integrated intensities of the IR bands arising from the C-H stretching vibrations indicates H-bonding between the C-H groups of TBE and the solvent. The enthalpies of specific interactions due to hydrogen bonding were estimated using the intensity rule (1–3 kcal/mole). The absence of correlations between ΔG0 and the solvent basicity parameter leads us to conclude that the trans- and gosh-conformers of TBE form nearly equally strong hydrogen bonds.
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V. V. Samoshin and N. S. Zefirov,Zh. Vses. Khim. Ova D. I. Mendeleeva,29, No. 5, 521–530 (1984).
R. J. Abraham and E. Bretschneider, in:Internal Rotation of Molecules, W. J. Orville-Thomas (ed.), Wiley, New York (1974).
R. J. Abraham, E. J. Chambers, and W. A. Thomas,J. Chem. Soc., Faraday Trans. 2,5, 949–955 (1994).
R. J. Abraham, T. A. D. Smith, and W. A. Thomas, ibid.,9, 1949–1955 (1996).
K. B. Wiberg, T. A. Keith, M. J. Frisch, and M. A. Murcko,J. Phys. Chem.,99, No. 22, 9072–9079 (1995).
J. M. Depaepe and J. P. Rykaert,Chem. Phys. Lett.,245, No. 6, 653–659 (1995).
E. Vilaseca,J. Chem. Phys.,104, No. 11, 4243–4257 (1996).
W. A. Herrebout and B. J. Van der Veken,J. Phys. Chem.,100, No. 23, 9671–9677 (1996).
M. D. Borisover, A. A. Stolov, S. V. Izosimova, et al.,Zh. Fiz. Khim.,65, No. 3, 594–599 (1991).
I. Miyagawa,J. Chem. Soc. Jpn., Pure Chem. Sect.,75, No. 11, 1162–1176 (1954).
R. E. Kagarise and D. H. Rank,Trans. Faraday Soc.,48, No. 5, 394–400 (1952).
R. E. Kagarise,J. Chem. Phys.,24, No. 2, 300–305 (1956).
J. Lamb,Z. Elektrochem. Ber. Bun. Phys. Chem.,64, No. 1, 135–141 (1960).
F. Heatley and G. Allen,Mol. Phys.,16, No. 1, 77–89 (1969).
G. L. Carlson, W. G. Fateley, and J. Hiraishi,J. Mol. Struct.,6, No. 1, 101–116 (1970).
A. Weissberger, E. Proskauer, J. Raddick, and E. Tups,Organic Solvents: Physical Properties and Methods of Purification [Russian translation], Izdatelstvo Inostrannoi Literatury, Moscow (1958).
A. A. Stolov, D. I. Kamalova, S. A. Smirnov, et al.,Zh. Fiz. Khim.,67, No. 12, 2388–2392 (1993).
A. A. Stolov and A. B. Remizov,Spectrochim. Acta A,51, No. 11, 1919–1932 (1995).
A. A. Stolov, N. V. Kohan, and A. B. Remizov,Vibr. Spectrosc.,14, No. 1, 35–47 (1997).
L. M. Sverdlov, M. D. Kovner, and E. P. Krainov,Vibrational Spectra of Polyatomic Molecules [in Russian], Nauka, Moscow (1970).
E. L. Eliel and O. Hofer,J. Am. Chem. Soc.,95, No. 24, 8041–8045 (1973).
A. A. Stolov and A. B. Remizov,Zh. Fiz. Khim.,69, No. 3, 563–566 (1995).
G. C. Pimentel and A. L. McClellan,The Hydrogen Bond, Freeman, San Francisco (1960).
A. B. Iogansen, in:The Hydrogen Bond [in Russian], N. D. Sokolov (ed.), Nauka, Moscow (1981), pp. 112–155.
A. A. Stolov, M. D. Borisover, and B. N. Solomonov,J. Phys. Org. Chem.,9, No. 5, 241–251 (1996).
M. H. Abraham, P. L. Grellier, D. V. Prior, et al.,J. Chem. Soc., Perkin Trans. 2, No. 4, 521–529 (1990).
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Kazan State University. Kazan State Technological University. Translated fromZhurnal Strukturnoi Khimii, Vol. 39, No. 3, pp. 478–483, May–June, 1998.
This work was supported by RFFR grant No. 96-03-32171a.
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Stolov, A.A., Vinokurova, E.A., Kamalova, D.I. et al. Hydrogen bonds involving C-H groups of 1,1,2,2-tetrabromoethane and their effect on the conformation equilibrium. J Struct Chem 39, 388–392 (1998). https://doi.org/10.1007/BF02873647
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DOI: https://doi.org/10.1007/BF02873647