Abstract
The MNDO method was used to calculate the geometrical parameters and relative energy of the terminal tautomeric structures of 2-aminothiazoline and 2-iminothiazolidine. The hydrogen bond energy and barrier to proton transfer in the cyclic dimers of these molecules were evaluated. The amino and imino structure were assigned for a series of phenyl-, alkyl-, and alkenyl-2-aminothiazolines using IR and PMR spectroscopy.
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Literature Cited
L. M. Jackman and T. Jen, J. Am. Chem. Soc., 97, 2811 (1975).
T. Jen, B. Dienel, H. Bowman, J. Petta, A. Hilt, and B. Loev, J. Med. Chem., 15, 727 (1972).
J. Rabinowitz, Helv. Chim. Acta, 52, 255 (1969).
G. Toth and A. Almasy, Org. Magn. Reson., 19, 219 (1982).
G. Toth and J. Hemela, Acta Chim. Acad. Sci. Hung., 95, 71 (1977).
S. T. Cholpankulova, L. A. Tsoi, A. D. Silambaeva, G. A. Ryskieva, N. A. Alekseeva, and L. T. Kalkabaeva, Izv. Akad. Nauk KazSSR, Ser. Khim., 75 (1984).
P. Sohar and L. Toldy, Acta Chim. Acad. Sci. Hung., 75, 99 (1973).
L. Toldy and J. Liptak, Tetrahedron Lett., 4319 (1970).
E. M. Peresleni, Yu. N. Sheinker, N. P. Zosimova, and Yu. I. Pomerantsev, Zh. Fiz. Khim., 39, 92 (1965).
L. Toldy, P. Sohar, K. Farago, G. Toth, and L. Bartalis, Tetrahedron Lett., 2167 (1970).
J. Tamas and L. Toldy, Tetrahedron Lett., 2173 (1970).
G. Schwenker and K. Bosl, Pharmazie, 24, 653 (1969).
L. I. Mizrakh, L. Yu. Polonskaya, A. N. Gvozdetskii, and A. M. Vasil'ev, Zh. Obshch. Khim., 56, 73 (1986).
L. I. Mizrakh, L. Yu. Polonskaya, A. N. Gvozdetskii, A. M. Vasil'ev, and L. B. Karpunina, Zh. Obshch. Khim., in press.
M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc., 99, 4899 (1977).
G. Argay, A. Kalmann, D. Lazar, B. Ribar, and G. Toth, Acta Crystallogr., B33, 99 (1977).
S. Stankovic, B. Ribar, G. Argay, and A. Kalmann, Cryst. Struct. Commun., 9, 1147 (1980).
A. Kalmann, G. Argay, B. Ribar, and L. Toldy, Tetrahedron Lett., 4241 (1977).
P. Sohar, G. Feher, and L. Toldy, Org. Magn. Reson., 11, 9 (1978).
D. Petrovic, B. Ribar, G. Argay, A. Kalmann, and W. Nowicki, Acta Crystallogr., B33, 106 (1977).
R. Nakamura, K. Mashida, and S. Hayashi, J. Mol. Struct., 146, 101 (1986).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 981–988, July, 1989.
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Ivanova, T.M., Burshtein, K.Y., Mizrakh, L.I. et al. Amine-imine tautomerism of 2-aminothiazolines. Chem Heterocycl Compd 25, 824–829 (1989). https://doi.org/10.1007/BF00472758
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DOI: https://doi.org/10.1007/BF00472758