Abstract
Schiff bases of 2-substituted 5-aminopyrimidines were synthesized, and their liquid-crystal and dielectric properties were investigated. It is shown that narrow ranges of the existence of meso phases and a greater (as compared with benzyl-ideneanilines) tendency for the development of a smectic state are characteristic for 2-alkoxy-, 2-alkyl-, and 2-cyano-5-arylideneaminopyrimides. The introduction of an aryl substituent into the 2 position of the pyrimidine ring gives rise to a pronounced increase in the thermostability of the meso phase and significantly increases the range of its existence. The use of groups with higher dipole moments as terminal groups leads to the production of compounds with high positive dielectric anisotropies.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
V. V. Titov and A. I. Pavlyuchenko, Khim. Geterotsikl. Soedin., No. 1, 3 (1980).
I. Inukai, J. Electron. Eng., 16, 84 (1979).
A. Biering, D. Demus, L. Richter, H. Sackmann, A. Wiegeleben, and H. Zaschke, Mol. Cryst. Liq. Cryst., 62, 1 (1980).
J.-C. Dubois, Ann. Phys. (Paris), 3, 131 (1978).
C. S. Oh, Mol. Crystl. Liq., 19, 95 (1972).
R. A. Champa, Mol. Cryst. Liq. Cryst., 19, 233 (1973).
A. I. Pavluchenko, N. I. Smirnova, E. I. Kovshev, and V. V. Titov, J. Phys., 40, Colloq. C3-1 (1979).
D. J. Brown (editor), The Pyrimidines, Interscience, New York-London (1962), p. 321.
J. Bodeker and K. Couralt, J. Prakt. Chem., J. Prakt. Chem., 322, 336 (1980).
V. Krchnak and Z. Arnold, Collect. Czech. Chem. Commun., 40, 1384 (1975).
V. Krchnak and Z. Arnold, Collect. Czech. Chem. Commun., 40, 1396 (1975).
R. Urban and O. Schnider, Helv. Chim. Acta, 41, 1806 (1958).
T. J. Schwan and H. Tieckelmann, J. Org. Chem., 29, 941 (1964).
P. E. Fanta and E. A. Hedman, J. Am. Chem. Soc., 78, 1434 (1956).
L. D. Braitberg, M. Robin, H. L. Friedman, and E. T. Tisza, J. Am. Chem. Soc., 69, 2005 (1947).
M. P. L. Caton and J. F. W. McOmie, J. Chem. Soc. (C), No. 7, 836 (1968).
S. I. Torgova, V. T. Lazareva, V. V. Titov, and B. M. Bolotin, Liquid Crystals and Their Practical Application. Intercollegiate Collection [in Russian], Ivanovo (1976), p. 130.
O. A. Osipov, V. I. Minkin, and V. A. Kogan, Zh. Fiz. Khim., 37, 1492 (1963).
N. N. Kharabaev, V. A. Kogan, G. I. Bondarenko, and O. A. Osipov, Dokl. Akad. Nauk SSSR, 256, 1141 (1981).
A. S. Al-Tai, D. M. Hall, and A. R. Mears, J. Chem. Soc., Perkin Trans. II, No. 2, 133 (1976).
E. Denecke, K. Müller, and T. Bluhm, Org. Magn. Reson., 18, 68 (1982).
J. Riand, M. T. Chenon, and N. Lumbroso-Bader, Org. Magn. Reson., 9, 572 (1977).
D. Demus, H. Demus, and H. Zaschke, “Flüssige Kristalle in Tabellen, Leipzig: VEB Deutscher Verlag für Grundstoffindustrie (1974), p. 93.
M. I. Barnik, S. V. Belyaev, M. F. Grebenkin, V. G. Rumyantsev, V. A. Seliverstov, V. Tsvetkov, and N. M. Shtykov, Kristallografiya, 23, 805 (1978).
M. F. Grebenkin, V. A. Seliverstov, L. M. Blinov, and V. G. Chigrinov, Kristallografiya, 20, 894 (1975).
W. H. de Jeu, Physical Properties of Liquid Crystalline Materials, Gordon and Breach, New York (1980), p. 65.
M. Schadt, J. Chem. Phys., 56, 1494 (1972).
E. A. Guggenheim and G. Prue, Physicochemical Calculations [Russian translation], Inostr. Lit., Moscow (1958), p. 100.
V. Krchnak and Z. Arnold, Collect. Czech. Chem. Commun., 40, 1390 (1975).
Z. Arnold, J. Saulova, and V. Krchnak, Collect. Czech. Chem. Commun., 38, 2633 (1973).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1545–1552, November, 1982.
Rights and permissions
About this article
Cite this article
Mikhaleva, M.A., Lazareva, V.T., Grebenkin, M.F. et al. Synthesis of schiff bases of 2-substituted 5-aminopyrimidines and their mesomorphic properties. Chem Heterocycl Compd 18, 1201–1208 (1982). https://doi.org/10.1007/BF00506375
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00506375