A study was carried out on the reversible decomposition of dibromobromate anions in organic solvents and we found the equilibrium constants for the processes responsible for the distribution of active halogen and hydrogen halide between their different forms in solution. The capacity of the solvent to form hydrogen bonds with the bromide anion, the feasibility of forming a molecular complex with bromine, and the structure of the cation (in solutions with low ionizing capacity) were all found to affect the reversible decomposition of the dibromobromate anion.
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References
B. D. Stepin, V. E. Plyushchev, and A. A. Fakeev, Usp. Khim., 34, No. 11, 1881–1907 (1965).
A. I. Parker, P. Singh, and J. Avraamides, “Halogen-halide-organonitrile dectro chemical cell,” Australian Patent No. 538,999, IPC H 01 M 6/04, Publ. September 6, 1984.
G. Bellucci, G. Berti, R. Bianchini, et al., J. Org. Chem., 46, No. 11, 2315–2323 (1981).
G. Bellucci, R. Bianchini, R. Ambrosetti, and G. Ingrosso, J. Org. Chem., 50, No. 18, 3313–3318 (1985).
J. Berthelot and M. Fournier, Canad. J. Chem., 64, No. 3, 603–607 (1986).
C. Djerassi and C. R. Scholz, J. Am. Chem. Soc., 70, No. 1, 417–418 (1948).
D. B. Scaife and H. J. V. Tyrrell, J. Chem. Soc., No. 2, 386–392 (1958).
L. Rafael, Bromine Compounds, Elsevier, Amsterdam (1988), pp. 369–384.
Tian Xiang Wang, M. D. Kelley, J. N. Cooper, et al., Inorg. Chem., 33, No. 25, 5872–5878 (1994).
M.-F. Ruasse, J. Aubard, B. Galland, and A. Adenier, J. Phys. Chem., 90, No. 18, 4382–4388 (1986).
E. Bienvenue, R. Msika, and J.-E. Dubois, J. Chim. Phys., 77, No. 9, 803–807 (1980).
Yu. S. Simanenko, V. A. Savelova, T. M. Prokop'eva, et al., J. Org. Chem., 69, No. 26, 9238–9240 (2004).
A. I. Popov and R. F. Swensen, J. Am. Chem. Soc., 77, No. 14, 3724–3726 (1955).
I. V. Nelson and R. T. Iwamoto, J. Electroanal. Chem., No. 7, 218–221 (1964).
E. Benedetti, B. Di Blasio, and P. Baine, J. Chem. Soc., Perkin Trans II, No. 3, 500–503 (1980).
P. Groth and O. Hassel, Acta Chem. Scand., 18, No. 2, 402–408 (1964).
J.-E. Dubois and H. Herzog, Bull. Soc. Chim. France, No. 1, 57–61 (1963).
J. J. Navoa, F. Mota, and S. Alvarez, J. Phys. Chem., 92, No. 23, 6561–6566 (1988).
K. Nozaki and R. A. Ogg, J. Am. Chem. Soc., 64, No. 3, 697–704 (1942).
T. W. Nakagawa, L. J. Andrews, and R. M. Keefer, J. Phys. Chem., 61, No. 7, 1007–1008 (1957).
P. B. D. de la Mare, O. M. H. el Dusouqui, J. G. Tillet, and M. Zeltner, J. Chem. Soc., 5306–5317 (1964).
L. G. Oberg, Acta Chem. Scand., 41, No. 6, 422–425 (1987).
G. Bellucci, R. Bianchini, C. Chiappe, and R. Ambrosetti, J. Am. Chem. Soc., 111, No. 1, 199–202 (1989).
R. E. Buckles and J. P. Yuk, J. Am. Chem. Soc., 75, No. 20, 5048–5052 (1953).
C. Chiappe, F. Del Moro, and M. Raugi, Eur. J. Org. Chem., No. 18, 3501–3510 (2001).
R. LeGoaller, H. Handel, P. Labbe, and J.-L. Pierre, J. Am. Chem. Soc., 106, No. 6, 1694–1698 (1984).
R. Bianchini and C. Chiappe, J. Org. Chem., 57, No. 24, 6474–6478 (1992).
W. Gabes and D. J. Stufkens, Spectrochim. Acta A, 30, No. 9, 1835–1841 (1974).
A. L. Kanibolotskii, V. A. Mikhailov, and V. A. Savelova, Zh. Org. Khim., 30, No. 7, 1052–1058 (1994).
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Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 44, No. 5, pp. 298–305, September–October, 2008.
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Dorokhova, T.V., Mikhailov, V.A., Kanibolotskii, A.L. et al. Reversible dissociation of dibromobromates in organic solvents. Theor Exp Chem 44, 307–315 (2008). https://doi.org/10.1007/s11237-008-9042-9
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DOI: https://doi.org/10.1007/s11237-008-9042-9