Intramolecular hydrogen bond in substituted 3-hydroxypyridines |
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| Authors: | V P Lezina V F Bystrov B E Zaitsev N A Andronova L D Smirnov K M Dyumaev |
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| Institution: | (1) Institute of Chemical Physics, USSR;(2) Institute of Chemistry of Natural Products, AS USSR, USSR;(3) Scientific Research Institute for Organic Intermediates and Dyes, Moscow |
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| Abstract: | To explain the character of the intramolecular hydrogen bond in substituted 3-hydroxypyridines, the chemical shifts in the NMR spectra of the hydroxyl group and the IR spectra were studied. It was established that the stability of the intramolecular hydrogen bond of the O-H NR2 type in substituted 3-hydroxypyridines increases when compared with the corresponding phenols, while an opposite pattern is observed for bonds of the O-H02 N type. An approximate evaluation of the energy of the intramolecular hydrogen bond in substituted 3-hydroxypyridines was achieved. When reacting with bases of the same strength, 3-hydroxypyridine forms more stable complexes than phenol. |
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