The results of investigations into the formation of the various ionic forms of heteroarenium salts, their characteristics, and their reactivity are summarized. Salts containing (4n+2)π-electron aromatic cations (n = 0–3), including chalcogenopyrylium (O, S, Se), azinium, benzo- and dibenzoazinium, and chalcogenoazolium (O, S, Se, NR) ions are examined. In this system of compounds the relationships between the structure and the macroscopic characteristics of the heteroarenium salts (ionization constants, association/dissociation constants, distances of closest interionic approach) and the effect of the nature of the ionic forms in the solutions on their reactivity in heterolytic reactions are analyzed.
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References
H. van der Plas, Ring Transformations of Heterocycles, Academic Press, London, New York (1973), vol. 1, 2.
O. P. Shvaika and V. N. Artemov, Usp. Khim., 41, 1788 (1972).
A. T. Balaban, A. Dinculescu, G. N. Dorofeenko, G. W. Fischer, A. V. Koblic, and V. V. Mezheritskii, W. Schroth, in: A. R. Katritzky (editor), Advances in Heterocyclic Chemistry, Suppl. 2, Academic Press, New York (1982).
H. Ohno, Electrochemical Aspects of Ionic Liquids, John Wiley & Sons, Inc., New Jersey (2005).
D. Bourissou, O. Guerret, F. P. Gabbai, and G. Bertrand, Chem. Rev., 100, 39 (2000).
A. I. Arduengo, Acc. Chem. Res., 32, 913 (1999).
W. A. Herrmann, Angew. Chem., Int. Ed., 41, 1290 (2002).
O. P. Shvaika, N. I. Korotkikh, and A. F. Aslanov, Khim. Geterotsikl. Soedin., 1155 (1992). [Chem. Heterocycl. Comp., 28, 971 (1992)].
N. I. Korotkikh, O. P. Shvaika, G. F. Rayenko, A. V. Kiselyov, A. V. Knishevitsky, A. H. Cowley, J. N. Jones, and C. L. B. Macdonald, ARKIVOC, viii, 10 (2005).
W. Abraham, B. Dreher, D. Kreysig, N. A. Sadovskij, and M. C. Kuzmin, J. Prakt. Chem., 329, 569 (1987).
R. Robinson and R. Stokes, Solutions of Electrolytes [Russian translation], Khimiya, Moscow (1963).
R. M. Fuoss and F. Accascina, Electrolytic Conductance, Wiley-Interscience, New York (1959).
R. M. Fuoss, L. Onsager, and I. F. Skinner, J. Phys. Chem., 69, 2581 (1965).
N. A. Izmailov, Electrochemistry of Solutions [in Russian], Ed. 3, Khimiya, Moscow (1966).
W. Ebeling and J. Rose, J. Solution Chem., 10, 599 (1981).
E. Eger and A. Zalkind (editors), Methods of Measurement in Electrochemistry [Russian translation], Mir, Moscow (1977).
M. Hojo, T. Takiguchi, M. Hagiwara, H. Nagai, and Y. Imai, J. Phys. Chem., 93, 955 (1989).
L. M. Tucker and C. A. Kraus, J. Am. Chem. Soc., 69, 454 (1947).
I. Kuthan, S. Böhm, and V. Skala, Coll. Czech. Chem. Commun., 44, 99 (1979).
A. G. Gershikov and B. V. Panchenko, in: Structure of Organic Salts, Reactivity, and Reaction Mechanisms [in Russian], Naukova Dumka, Kiev (1988), p. 65.
S. Tamagaki and K. Batoh, J. Chem. Soc., Perkin Trans. 2, 1389 (2001).
R. M. Fuoss and C. A. Kraus, J. Am. Chem. Soc., 55, 2387 (1933).
N. A. Kovach and O. P. Shvaika, in: Molecular Interactions, Structure, and Reactivity of Organic Compounds [in Russian], Naukova Dumka, Kiev (1992), p. 148.
O. P. Shvaika and M. A. Kovach, Dokl. Akad. Nauk Ukraini, Ser. B, No. 12, 152 (1999); Ref. Zh. Khim., 15B3164 (2000). [O. P. Shvaika, M. A. Kovach, Dokl. Akad. Nauk Ukraini, Ser. B, No. 2, 148 (2000)].
O. P. Shvaika and M. A. Kovach, Dokl. Akad. Nauk UkrSSR, Ser. B, No. 12, 49 (1984); Ref. Zh. Khim., 12B3275 (1985).
N. A. Kovach, B. B. Ryvkin, T. D. Sadekov, and O. P. Shvaika, Zh. Org. Khim., 32, 886 (1996).
R. L. Buckson and S. A. Smith, J. Phys. Chem., 68, 1875 (1964).
O. P. Shvaika and N. A. Kovach, Zh. Org. Khim., 32, 572 (1996).
D. Dobosh, Electrochemical Constants [Russian translation], Mir, Moscow (1980).
O. P. Shvaika, N. A. Kovach, O. N. Chupakhin, and V. N. Charushin, Zh. Org. Khim., 32, 941 (1996).
Yu. B. Visots’kii and O. P. Shvaika, Dokl. Akad. Nauk UkrSSR, Ser. B, 804 (1975).
N. A. Kovach, I. P. Krainov, I. Yu. Grineva, and O. P. Shvaika, Zh. Org. Khim., 32, 625 (1996).
E. V. Titov and V. I. Rybachenko, J. Mol. Struct., 60, 67 (1980).
E. V. Titov, V. I. Rybachenko, L. D. Goncharova, and R. G. Semenova, Zh. Fiz. Khim., 54, 3099 (1980).
E. V. Titov, K. Yu. Chotii, and V. I. Rybachenko, Zh. Obshch. Khim., 51, 682 (1981).
E. V. Titov, V. I. Rybachenko, K. Yu. Chotii, and L. D. Goncharova, in: Intermolecular Interactions, Structure, and Reactivity of Organic Compounds [in Russian], Naukova Dumka, Kiev (1983), p. 23.
N. A. Kovach and O. P. Shvaika, The Nature of the Ionic Forms of Arcationoid Compounds [in Russian], Dep. VINITI 10.04.84, No. 2980-84; Ref. Zh. Khim., 17B3227DP (1984).
V. I. Rybachenko, E. V. Titov, I. P. Gol’dshtein, L. V. Grebenyuk, K. Yu. Chotii, and R. G. Semenova, Zh. Fiz. Khim., 71, 248 (1997).
E. V. Titov, R. A. Makarova, V. I. Rybachenko, K. Yu. Chotii, and L. D. Goncharova, Teoret. Eksper. Khim., 24, 227 (1988).
K. Yu. Chotii, V. I. Rybachenko, and E. V. Titov, Zh. Org. Khim., 32, 604 (1996).
R. G. Semenova, V. I. Rybachenko, E. V. Titov, L. I. Kozhevina, K. Yu. Chotii, and K. Agbodan, Zh. Obshch. Khim., 64, 2032 (1994).
S. G. Sheiko, T. P. Kuleshova, and A. A. Dubovaya, Ukr. Khim. Zh., 57, 877 (1991).
G. D. Titskii, E. S. Mitchenko, and A. A. Dubovaya, Zh. Org. Khim., 24, 2156 (1988).
E. L. M. Kosower, and J. C. Bureach, J. Am. Chem. Soc., 78, 5838 (1956).
R. A. Mackay and E. J. Poziomek, J. Am. Chem. Soc., 92, 2432 (1970).
J. C. Nichol and R. M. Fuoss, J. Am. Chem. Soc., 77, 198 (1955).
A. Mukhopadhyay, A. Nandi, M. Pal, and S. Bagchi, Ind. J. Chem., 33A, 297 (1994).
S. Tamagaki and K. Batoh, J. Chem. Soc., Perkin Trans. 2, 1389 (2001).
M. Watanabe, S. Yamada, and N. Ogata, Electrochim. Acta, 40, 2285 (1995).
S. A. Lapshin, L. M. Kapkan, F. Yu. Chervinskii, R. Lange, and L. M. Litvinenko, Dokl. Akad. Nauk, 278, 1405 (1984).
L. M. Litvinenko, O. Yu. Chervinskii, S. O. Lapshin, L. M. Kapkan, V. V. Fedorov, and S. Yu. Suikov, Dokl. Akad. Nauk UkrSSR, Ser. B, No. 6, 36 (1984).
S. A. Lapshin, L. M. Kapkan, Yu. I. Smirnov, V. V. Fedorov, and L. M. Litvinenko, Dokl. Akad. Nauk UkrSSR, Ser. B, No. 9, 47 (1985).
S. A. Lapshin, L. M. Kapkan, A. Yu. Chervinskii, V. V. Fedorov, and R. Lange, Zh. Org. Khim., 21, 1389 (1985).
S. A. Lapshin, L. M. Kapkan, and L. M. Litvinenko, Dokl. Akad. Nauk, 281, 1396 (1985).
L. M. Kapkan, S. A. Lapshin, and Yu. I. Smirnov, Teor. Eksp. Khim., 23, 497 (1987).
S. A. Lapshin, L. M. Kapkan, V. V. Fedorov, and Yu. I. Smirnov, Zh. Org. Khim., 25, 2055 (1989).
V. D. Pokhodenko and V. V. Pavlishchuk, Teor. Eksp. Khim., 38, 67 (2002).
L. M. Kustov and I. P. Beletskaya, Ros. Khim. Zh., 48, № 6, 3 (2004).
W. J. Li, Z. F. Zhang, B. X. Han, S. Q. Hu, Y. Xie, and G. Y. Yang, J. Phys. Chem. B, 111, 6452 (2007).
R. A. Ando, L. J. A. Siqueira, F. C. Bazito, R. M. Torresi, and P. S. Santos, J. Phys. Chem. B, 111, 8717 (2007).
N. Noujeim, L. Leclercq, and A. R. Schmitzer, J. Org. Chem., 73, 3784 (2008).
K. Tian, Y. S. Wang, Y. L. Chen, Y. G. Chen, and Z. D. Hu, Talanta, 72, 587 (2007).
H. Ohno, M. Yoshizawa, and W. Ogihara, Electrochim. Acta, 50, 255 (2004).
Y. S. Vygodskii, O. A. Melnik, A. S. Shaplov, E. I. Lozinskaya, I. A. Malyshkina, and N. D. Gavrilova, Polym. Sci., Ser. A, 49, 256 (2007).
B. Yu, F. Zhou, C. W. Wang, and W. M. Liu, Europ. Polym. J., 43, 2699 (2007).
I. Ya. Bernshtein and Yu. L. Kaminskii, Spectrophotometric Analysis in Organic Chemistry [in Russian], Ed. 2, Khimiya, Leningrad (1986).
J. Gordon, Organic Chemistry of Electrolytic Solutions [Russian translation], Mir, Moscow (1979).
V. A. Tafeenko and L. A. Aslanov, Zh. Struktur Khim., 21, No. 6, 79 (1980).
A. T. Balaban and M. D. Gheorghiu, Rev. Roum. Chim., 23, 1065 (1978).
P. Bacelon, J. Corset, and C. de Loze, J. Solut. Chem., 9, 129 (1980).
O. P. Shvaika and V. I. Fomenko, Zh. Org. Khim., 10, 377 (1974).
O. P. Shvaika and V. I. Fomenko, Zh. Org. Khim., 10, 2429 (1974).
O. P. Shvaika and V. F. Lipnitskii, Zh. Obshch. Khim., 51, 1842 (1981).
O. P. Shvaika and V. F. Lipnitskii, Zh. Obshch. Khim., 55, 2608 (1985).
M. A. Kovach and O. P. Shvaika, Dokl. Akad. Nauk Ukraini, No. 7, 143 (2002); Ref. Zh. Khim., 24B452 (2003).
V. N. Charushin, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 4, 65 (1990).
V. A. Savelova and N. M. Oleinik, Mechanism of the Action of Organic Catalysts. Bifunctional and Intramolecular Catalysis [in Russian], Naukova Dumka, Kiev (1990).
L. M. Litvinenko and N. M. Oleinik, Mechanism of the Action of Organic Catalysts. Base and Nucleophilic Catalysis [in Russian], Naukova Dumka, Kiev (1984).
V. I. Rybachenko, G. Shreder, B. Lenska, K. Yu. Chotii, R. G. Semenova, R. A. Makarova, and L. V. Grebenyuk, Teor. Eksp. Khim., 33, 143 (1997).
V. I. Rybachenko, G. Shreder, V. M. Gokhfel’d, K. Yu. Chotii, V. V. Kovalenko, and B. Lenska, Zh. Obshch. Khim., 74, 1720 (2004).
V. I. Rybachenko, G. Shreder, K. Yu. Chotii, V. V. Kovalenko, and K. Either, Teor. Eksp. Khim., 37, 231 (2001).
V. I. Rybachenko, G. Shreder, K. Yu. Chotii, and V. V. Kovalenko, Teor. Eksp. Khim., 34, 96 (1998).
G. Shreder, V. I. Rybachenko, K. Yu. Chotii , V. V. Kovalenko, L. V. Grebenyuk, B. Lanska, and K. Either, Zh. Obshch. Khim., 73, 486 (2003).
V. I. Rybachenko, G. Shreder, K. Yu. Chotii, V. V. Kovalenko, A. N. Red’ko, and B. Lenska, Zh. Obshch. Khim., 78, 1013 (2008).
V. I. Rybachenko, G. Shreder, K. Yu. Chotii, V. V. Kovalenko, B. Lenska, A. N. Red’ko, and V. V. Kovalenko, Zh. Org. Khim., 41, 788 (2005).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1603–1621, November, 2009.
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Shvaika, O.P., Kovach, N.A. Structure and characteristics of the ionic forms of heteroarenium salts in organic solvents (review). Chem Heterocycl Comp 45, 1287–1301 (2009). https://doi.org/10.1007/s10593-010-0424-2
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DOI: https://doi.org/10.1007/s10593-010-0424-2