Abstract
It was established by X-ray crystallographic analysis that 4,6-dimethyl-2-(phenylhydrazino)pyrimidine forms 2-(2-n-butyl-2-phenylhydrazino)-4,6-dimethylpyrimidine during alkylation with n-butyl bromide and 4,6-dimethyl-2-(phenylhydrazino)-1(H)-pyrimidinium nitrate during protonation with nitric acid. The structure of the molecules and the system of intermolecular hydrogen bonds in the crystals of the compounds are discussed.
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REFERENCES
F. N. Allen, O. Kennard, D. G. Watson, L. Bramer, A. G. Orpen, and R. Taylor, J. Chem. Soc. Perkin Trans. 2, 1 (1987).
B. I. Buzykin, A. T. Gubaidullin, I. A. Litvinov, N. G. Gazetdinova, and L. P. Sysoeva, Zh. Obshch. Khim., 68, 1972 (1998).
A. Cousson, F. Nectoux, B. Bachet, B. Kokel, and M. Hubert-Habart, Acta Crystallogr., C50, 1753 (1994).
T. Ottersen, Acta Chem. Scand., A28, 1145 (1974).
V. Kh. Kravtsov, Yu. A. Simonov, N. V. Gerbeleu, O. A. Bologa, V. I. Lozan, and T. I. Malinovskii, Zh. Strukt. Khim., 35, No. 3, 154 (1994).
Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974), p. 80.
B. I. Buzykin, N. N. Bystrykh, A. P. Stolyarov, S. A. Flegontov, V. V. Zverev, and Yu. P. Kitaev, Khim. Geterotsikl. Soedin., 402 (1976).
B. I. Buzykin, N. N. Bystrykh, A. P. Stolyarov, L. V. Belova, and Yu. P. Kitaev, Khim. Geterotsikl. Soedin., 699 (1978).
L. V. Vilkov, V. S. Mastryukov, and N. I. Sadova, Determination of the Geometric Structure of Free Molecules [in Russian], Khimiya, Leningrad (1978), p. 224.
A. Yamaguchi, J. Ishishima, J. Shimanouchi, and S. Mizushima, J. Chem. Phys., 31, 843 (1959).
R. P. Lattimer and M. D. Harmony, J. Chem. Phys., 53, 4575 (1970).
O. A. Litvinov, L. V. Ermolaeva, V. V. Zverev, and V. A. Naumov, Zh. Strukt. Khim., 30, No. 2, 64 (1989).
M. Nakata, H. Takeo, C. Matsumura, K. Yamanouchi, K. Kuchitsu, and T. Furuyama, Chem. Phys. Lett., 83, 246 (1981).
I. A. Litvinov, Yu. T. Struchkov, N. N. Bystrykh, Yu. P. Kitaev, and B. I. Buzykin, Khim. Geterotsikl. Soedin., 977 (1982).
A. L. Spek, Acta Crystallogr., A46, 34 (1990).
L. H. Straver and A. J. Schierbeer, MolEN. Structure Determination System. Program Description, Nonius B. V., Delft (1994), Vol. 1, p. 180.
A. Altomare, G. Cascarano, C. Giacovazzo, and D. Viterbo, Acta Crystallogr., A47, 744 (1991).
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Buzykin, B.I., Sorokin, M.Y., Krivolapov, D.B. et al. Molecular and Crystal Structure of 4,6-Dimethyl-2-(phenylhydrazino)pyrimidine and Its Alkylation and Protonation Products. Chemistry of Heterocyclic Compounds 38, 1348–1356 (2002). https://doi.org/10.1023/A:1022178425960
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DOI: https://doi.org/10.1023/A:1022178425960