Abstract
The simple MO LCAO method was used to calculate the isomeric N,N-dimethylhypoxanthines and the corresponding 2(6)-ethoxy- and 2(6)-ethoxy-8-chloro derivatives, and the PMR spectra of a number of compounds of this type were measured. A qualitative correlation was observed between changes in the π -electron densities and changes in the chemical shifts of the protons of the N-methyl groups. Factors affecting the alkylating capacity of 2(6)-alkoxypurines and the direction of the reaction of these compounds with sodiomalonic ester when the molecules contain two different reaction centers were examined. The use of the π -electron densities and orders and polarizabilities of the heterocycle — substituent bonds as reactivity indexes makes it possible to explain the highest alkylating capacity of 2-ethoxy-3,7-dimethylhypoxanthine and its 8-chloro derivative and the order of other compounds with respect to this capacity.
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E. S. Golovchinskaya, V. S. Korsunskii, O. V. Kozlova, and T. D. Pervacheva, Khim.-Farmats. Zh., No. 11, 20 (1969).
B. Pullman and A. Pullman, Quantum Biochemistry, Wiley (1963).
W. W. Paudler and I. E. Kuder, J. Heterocycl. Chem., 3, 33 (1966).
G. G. Dvoryantseva, V. P. Lezina, V. F. Bystrov, T. N. Ul'yanova, G. P. Syrova, and Yu. N. Sheinker, Izv. Akad. Nauk SSSR, Ser. Khim., 994 (1968).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 265–271, February, 1971.
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Ul'yanova, T.N., Dvoryantseva, G.G., Kostyuchenko, N.P. et al. Electronic structure, PMR spectra, and alkylating capacity of some 2- and 6-alkoxypurines. Chem Heterocycl Compd 7, 243–248 (1971). https://doi.org/10.1007/BF00473099
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DOI: https://doi.org/10.1007/BF00473099