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One factor to consider is the role of hydrogen bonding. In the gas phase at low pressure there is no hydrogen bonding because the molecules are too isolated; then the hydroxyl form with a pure cyclic conjugation = maximum aromaticity is more stable. In the neat liquid or in a polar solvent, the keto form will have stronger hydrogen bonding due to the ...


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Why not start with the corresponding entry in Wikipedia as suggested in the comment by @Maurice? There, it discerns the solid state «The predominant solid state form is 2-pyridone. This has been confirmed by X-ray crystallography which shows that the hydrogen in solid state is closer to the nitrogen than to the oxygen (because of the low electron density ...


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