Abstract
It was shown by UV spectroscopy that the introduction of CH3 and CH2Ph groups into the 2 position of 3-hydroxypyridine and its N-oxides does not have a substantial effect on the acidbase transformations of these compounds. The effect of methyl and benzyl groups on the electronic and energy characteristics of 3-hydroxypyridine and its N-oxide was studied by means of perturbation theory within the framework of the Hückel MO method. The reactivity indexes (RI) of 2-methyl- and 2-benzyl-3-hydroxypyridines and their N-oxides were calculated, and the RI were correlated with the experimentally observed regularity of the orientation of electrophilic substitution in the indicated compounds.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 216–220, February, 1975.
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Grachev, V.T., Zaitsev, B.E., Zhuravlev, V.S. et al. Structures and reactivities of 2-methyl- and 2-benzyl-3-hydroxypyridines and their N-oxides. Chem Heterocycl Compd 11, 185–189 (1975). https://doi.org/10.1007/BF00471394
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DOI: https://doi.org/10.1007/BF00471394