Predicting Hydrogen Bonding in 2-Pyridone Dimers

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The 2-Pyridone system serves as a model to study lactam–lactim tautomerism, forming dimers through N–H···O=C hydrogen bonding, with a focus on 3-position substitution effects. Using M06-L/6-311++G(d,p) optimization, results indicate exothermic dimer formation with varying energies, most significant in O⁻ and least in AsO₃H⁻. Hydrogen bond geometry reveals Δr reflects bond asymmetry, with O⁻ exhibiting the highest Δr. ¹H NMR and electrostatic studies show Δσ correlates with Δr and bond...