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Tautomerism and Microsolvation in 2-Hydroxypyridine/2-Pyridone

2010; American Chemical Society; Volume: 114; Issue: 43 Linguagem: Inglês

10.1021/jp104625z

1520-5215

Santiago Mata, Vanessa Cortijo, Walther Camináti, José L. Alonso, M. Eugenia Sanz, Juan C. López, Susana Blanco,

Organic and Inorganic Chemical Reactions

The Fourier transform microwave spectra of the hydrated forms of the tautomeric pair 2-pyridinone/2-hydroxypyridine (2PO/2HP) have been investigated in a supersonic expansion. Three hydrated species, 2PO−H2O, 2HP−H2O, and 2PO−(H2O)2, have been observed in the rotational spectrum. Each molecular complex was confidently identified by the features of the 14N quadrupole hyperfine structure of the rotational transitions. The presence of water affects the tautomeric equilibrium −N═C(OH)− ↔ −NH−C(═O)−, which is shifted to the enol form for the bare molecules 2PO/2HP but to the keto tautomer for the hydrated forms.