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On the Tautomerism of N-Substituted Pyrazolones: 1,2-Dihydro-3H-pyrazol-3-ones versus 1H-Pyrazol-3-ols.

The tautomerism of 1-phenyl-1,2-dihydro-3 H -pyrazol-3-One was investigated. An X-ray crystal structure analysis exhibits dimers of 1-phenyl-1 H -pyrazol-3-ol units. Comparison of NMR (nuclear magnetic resonance) spectra in liquid state (¹H, 13 C, 15 N) with those of "fixed" derivatives, as well as with the corresponding solid state NMR spectra reveal this compound to exist predominantly as 1 H -pyrazol-3-ol molecule pairs in nonpolar solvents like CDCl₃ or C₆D₆, whereas in DMSO- d ₆ the corresponding monomers are at hand. Moreover, the NMR data of different related 1 H -pyrazol-3-ol derivatives are presented.

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