Abstract
The dipole moments of some 1-pyridylpyrazoles and their 5-amino derivatives have been determined. On the basis of the experimental findings and of vector calculations of the magnitudes of the dipole moments, it has been established that the structure of the 1-pyridylpyrazoles and 1-(3′- or 4′-pyridyl)-5-aminopyrazoles is nonplanar, and the angle between the planes of the pyrazole and pyridine rings has been calculated. For 1-(2′-pyridyl)-5-aminopyrazoles, intramolecular hydrogen bonding leads to the occurrence of the planar trans configuration.
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References
L. N. Ferguson, Chem. Rev., 43, 385, 1948.
Steric Effects in Organic Chemistry [Russian translation], IL, Moscow, 486, 1960.
E. Eliel, The Stereochemistry of Carbon Compounds [Russian translation], Mir, Moscow, 155, 1965.
C. W. N. Cumper, R. F. A. Ginman, and A. I. Vogel, J. Chem. Soc., 1188, 1962.
Physical Methods in the Chemistry of Heterocyclic Compounds [in Russian], Khimiya, Moscow, 209, 1966.
A. F. Pozharskii and A. M. Simonov, ZhOKh, 34, 224, 1964.
I. I. Grandberg, S. V. Tabak, and A. N. Kost, KhGS [Chemistry of Heterocyclic Compounds], 901, 1965.
I. I. Grandberg and N. F. Krokhina, Izv. TSKhA, 6, 193, 1967.
N. F. Krokhina, Candiate's dissertation, Moscow, 1967.
B. Eda and K. Ito, Bull. Chem. Soc. Japan, 29, 524, 1956.
V. I. Minkin, O. A. Osipov, and Yu. A. Zhdanov, Dipole Moments [in Russian], Khimiya, Leningrad, 1968.
O. A. Osipov and V. I. Minkin, Handbook of Dipole Moments [in Russian], Vysshaya shkola, Moscow, 1965.
S. A. Hiller, I. B. Mazheika, and I. I. Grandberg, KhGS [Chemistry of Heterocyclic Compounds], 103, 1965.
S. A. Hiller, I. B. Mazheika, and I. I. Grandberg, KhGS [Chemistry of Heterocyclic Compounds], 107, 1965.
J. W. Smith, J. Chem. Soc., 81, 1961.
C. P. Smyth, Dielectric Behaviour and Structure, N. Y.-London, 1955.
V. G. Vinokurov, V. S. Troitskaya, and I. I. Grandberg, ZhOKh, 34, 654, 1964.
E. Braude and F. Sondheimer, J. Chem. Soc., 3754, 1955.
H. Sazuki, Bull. Chem. Soc. Japan, 32, 1340, 1959.
F. N. Lindon and S. K. Livingstone, Coord. Chem. Rev., Amsterdam, 2, 172, 1967.
A. N. Kost and I. I. Grandberg, Adv. Heterocyclic Chem., 6, 407, 1966.
O. A. Osipov, ZhOKh, 26, 322, 1956.
R. T. Nigmatulin, M. R. Vyaselev, and V. S. Shatunov, Zav. lab., 30, 500, 1964.
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Alieva, S.A., Kolodyazhnii, Y.V., Garnovskii, A.D. et al. Nitrogen-containing bisheterocyclic systems. Chem Heterocycl Compd 6, 42–45 (1970). https://doi.org/10.1007/BF00475421
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DOI: https://doi.org/10.1007/BF00475421