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Tautomerism and Acid-Base Properties of Formyl Derivatives of 1-Phenyl-3-methyl-4,5-dihydropyrazol-5-one and Its Thio Analog

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Abstract

A single-crystal X-ray diffraction study showed that 1-phenyl-3-methyl-4-formyl-4,5-dihydropyrazol-5-one occurs in the solid phase as two conformers of the NH tautomer. The acidity and basicity constants of 1-phenyl-3-methyl-4-formyl-4,5-dihydropyrazol-5-one and its analog, -5-thione, in 50% aqueous dioxane were measured. PM3 calculations qualitatively explan the differences in the tautomerism and acid-base properties of 4-formylpyrazolone (-pyrazolethione) and the corresponding compounds without the formyl substituent.

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Authors and Affiliations

  1. Kazan State University, Kazan, Tatarstan, Russia

    A. I. Movchan, A. R. Kurbangalieva, O. N. Kataeva, I. A. Litvinov & G. A. Chmutova

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Tatarstan, Russia

    A. I. Movchan, A. R. Kurbangalieva, O. N. Kataeva, I. A. Litvinov & G. A. Chmutova

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  1. A. I. Movchan
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  2. A. R. Kurbangalieva
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  3. O. N. Kataeva
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  4. I. A. Litvinov
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  5. G. A. Chmutova
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Movchan, A.I., Kurbangalieva, A.R., Kataeva, O.N. et al. Tautomerism and Acid-Base Properties of Formyl Derivatives of 1-Phenyl-3-methyl-4,5-dihydropyrazol-5-one and Its Thio Analog. Russian Journal of General Chemistry 73, 1130–1136 (2003). https://doi.org/10.1023/B:RUGC.0000007624.57825.22

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  • DOI: https://doi.org/10.1023/B:RUGC.0000007624.57825.22

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