Abstract
Betaine aldehydes of thiazole and imidazole containing substituted pyridinium and isoquinolinium cations were synthesized and their basicities were determined. The effect of the type of charge separation (betaine and ylid) and the nature of the heteroatoms and substituents in the onium and anionoid parts of the molecules on their electronic spectra and basicities was studied; the principles established are presented in the form of linear dependences.
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Literature Cited
A. Johnson, The Chemistry of Ylids [Russian translation], Mir, Moscow (1969).
I. D. Sadekov, V. I. Minkin, V. V. Semenov, and S. A. Shevelev, Usp. Khim., 50, 813 (1981).
Yu. V. Belkin and N. A. Polezhaeva, Usp. Khim., 50, 925 (1981).
R. O. Kochkanyan, A. N. Zaritovskii, G. I. Belova, and S. N. Baranov, Khim. Geterotsikl. Soedin., No. 2, 278 (1975).
R. O. Kochkanyan, N. V. Spitsyn, and S. N. Baranov, Khim. Geterotsikl. Soedin., No. 4, 505 (1983).
O. Ya. Neiland and S. V. Kalnin', Zh. Org. Khim., 4, 140 (1976).
I. D. Sadekov, A. I. Usachev, A. A. Maksimenko, and V. I. Minkin, Zh. Obshch. Khim., 45, 2563 (1975).
I. D. Sadekov, A. I. Usachev, V. A. Bren', M. S. Korobov, I. D. Tseimakh, and V. I. Minkin, Zh. Obshch. Khim., 47, 2232 (1977).
S. N. Baranov, R. O. Kochkanyan, A. N. Zaritovskii, G. I. Belova, and S. S. Radkova, Khim. Geterotsikl. Soedin., No. 1, 85 (1975).
L. Andrews and R. Kiefer, Molecular Complexes in Organic Chemistry [Russian translation], Mir, Moscow (1967), p. 208.
E. J. Kosower, An Introduction to Physical Organic Chemistry, Part 2, Wiley-Interscience, New York (1968).
H. Lumbroso, D. Lloid, and G. S. Harris, Compt. Rend., C, 378, 219 (1974).
K. L. Ratts, J. Org. Chem., 37, 848 (1972).
L. Bellamy, New Data on the IR Spectra of Complex Molecules [Russian translation], Mir, Moscow (1971), p. 300.
S. N. Baranov, L. M. Zueva, A. N. Zaritovskii, and R. O. Kochkanyan, Summaries of Papers Presented at the 14th Ukrainian Republican Conference on Organic Chemistry [in Russian] (1982), p. 18.
O. Ya. Neiland, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 1, 64 (1971).
V. é. Kampar and O. Ya. Neiland, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 727 (1975).
A. Ratajczak and V. G. Orville-Thomas (eds.), Molecular Interactions [Russian translation], Mir, Moscow (1984), p. 276.
O. Ya. Neiland, R. V. Kampare, D. é. Prikule, and é. é. Liepin'sh, Khim. Geterotsikl. Soedin., No. 3, 379 (1979).
P. Huyskens, J. Mol. Struct. Theor. Chem., 135, 67 (1986).
R. O. Kochkanyan, A. N. Zaritovskii, L. A. Klyuev, B. M. Zolotarev, and S. N. Baranov, Khim. Geterotsikl. Soedin., No. 2, 255 (1978).
H. C. Brown and W. A. Murphey, J. Am. Chem. Soc., 73, 3308 (1951).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 246–251, February, 1990.
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Kochkanyan, R.O., Spitsyn, N.V., Korzhenevskaya, N.G. et al. Effect of structural factors on the basicities and electronic spectra of betaine aldehydes of azoles and ylids of malonic ester and dimedone. Chem Heterocycl Compd 26, 212–217 (1990). https://doi.org/10.1007/BF00499419
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DOI: https://doi.org/10.1007/BF00499419