Structures of 3-hydroxy-1-(2-methoxyethyl)-2-methyl-4-pyridinone, its hydrochloride and 1-ethyl-3-hydroxy-2-methyl-4-pyridinone hydrochloride hydrate.
3-Hydroxy-1-(2-methoxyethyl)-2-methyl-4(1H)-pyridinone (1) exists mainly in the quinoid form with a small contribution from the aromatic zwitterion form, while 3-hydroxy-1-(2-methoxyethyl)-2-methyl-4(1H)-pyridinone hydrochloride (2) and 1-ethyl-3-hydroxy-2-methyl-4(1H)-pyridinone hydrochloride hydrate (3) are observed to occur in the aromatic form with a minor contribution from the quinoid resonance form. Different substituents at the ring N position do not have significant geometric effects in either the neutral molecules, as a group, or in the hydrochloride salts.
Xiao
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G
University of Oklahoma, Norman 73019.
van der Helm
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D
Goerlitz
F H
FH
Hider
R C
RC
Dobbin
P S
PS
D018360:Crystallography, X-Ray; D007502:Iron Chelating Agents / Q000737:chemistry*; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*
D007502:Iron Chelating Agents; D011728:Pyridones; C084282:3-hydroxy-1-(2-methoxyethyl)-2-methyl-4-pyridinone; C048630:1-ethyl-2-methyl-3-hydroxypyridin-4-one