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Derivatives of 1-phenyl-3-methylpyrazol-2-in-5-thione and their oxygen analogues in the crystalline phase and their tautomeric transformations in solutions and in the gas phase |
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| Authors: | Galina A Chmutova Olga N Kataeva Hubertus Ahlbrecht Almira R Kurbangalieva Alexander I Movchan Albert T H Lenstra Herman J Geise Igor A Litvinov |
| Institution: | a Kazan State University, Kremlevskaya 18, Kazan 420008, Russia b A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, A.E. Arbuzov str. 8, Kazan 420088, Russia c Institut für Organische Chemie, Justus-Liebig-Universität Giessen, Heinrich-Buff-Ring 58, D-35392, Germany d University of Antwerpen (UIA), Department of Chemistry, Universiteitsplein 1, B-2610 Antwerpen (Wilrijk), Belgium |
| Abstract: | 1-Phenyl-3-methylpyrazol-2-in-5-thione, crystallised from methanol, was shown to exist in the tautomeric NH-form, stabilised by intermolecular NH S hydrogen bonds. In solutions, however, the molecule is found predominantly as the SH-tautomer, accompanied (in low-polar solvents) by a small amount of the CH-tautomer.1-Phenyl-3-methyl-4-benzoylpyrazol-2-in-5-thione occurs in the crystal as well as in solution in the SH-tautomeric form, stabilised by an intramolecular SH The structure of 1-phenyl-3-methylpyrazol-2-in-5-one was redetermined by X-ray single crystal diffraction at 120°K in order to obtain more accurate geometry and hydrogen bonding parameters. |
| Keywords: | Thiopyrazolones and pyrazolones Tautomerism X-ray single crystal diffraction Ab initio calculations |
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