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-3H-pyrazol-3-one was investigated. An X-ray crystal structure analysis exhibits dimers of 1-phenyl-1H-pyrazol-3-ol units. Comparison of NMR (nuclear magnetic resonance) spectra in liquid state ((1)H, (13)C, (15)N) with those of “fixed” derivatives, as well as...

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Autores principales: Arbačiauskienė, Eglė, Krikštolaitytė, Sonata, Mitrulevičienė, Aiva, Bieliauskas, Aurimas, Martynaitis, Vytas, Bechmann, Matthias, Roller, Alexander, Šačkus, Algirdas, Holzer, Wolfgang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017633/
https://www.ncbi.nlm.nih.gov/pubmed/29315238
http://dx.doi.org/10.3390/molecules23010129
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author Arbačiauskienė, Eglė
Krikštolaitytė, Sonata
Mitrulevičienė, Aiva
Bieliauskas, Aurimas
Martynaitis, Vytas
Bechmann, Matthias
Roller, Alexander
Šačkus, Algirdas
Holzer, Wolfgang
author_facet Arbačiauskienė, Eglė
Krikštolaitytė, Sonata
Mitrulevičienė, Aiva
Bieliauskas, Aurimas
Martynaitis, Vytas
Bechmann, Matthias
Roller, Alexander
Šačkus, Algirdas
Holzer, Wolfgang
author_sort Arbačiauskienė, Eglė
collection PubMed
description The tautomerism of 1-phenyl-1,2-dihydro-3H-pyrazol-3-one was investigated. An X-ray crystal structure analysis exhibits dimers of 1-phenyl-1H-pyrazol-3-ol units. Comparison of NMR (nuclear magnetic resonance) spectra in liquid state ((1)H, (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 1H-pyrazol-3-ol molecule pairs in nonpolar solvents like CDCl(3) or C(6)D(6), whereas in DMSO-d(6) the corresponding monomers are at hand. Moreover, the NMR data of different related 1H-pyrazol-3-ol derivatives are presented.
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spelling pubmed-60176332018-11-13 On the Tautomerism of N-Substituted Pyrazolones: 1,2-Dihydro-3H-pyrazol-3-ones versus 1H-Pyrazol-3-ols Arbačiauskienė, Eglė Krikštolaitytė, Sonata Mitrulevičienė, Aiva Bieliauskas, Aurimas Martynaitis, Vytas Bechmann, Matthias Roller, Alexander Šačkus, Algirdas Holzer, Wolfgang Molecules Article The tautomerism of 1-phenyl-1,2-dihydro-3H-pyrazol-3-one was investigated. An X-ray crystal structure analysis exhibits dimers of 1-phenyl-1H-pyrazol-3-ol units. Comparison of NMR (nuclear magnetic resonance) spectra in liquid state ((1)H, (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 1H-pyrazol-3-ol molecule pairs in nonpolar solvents like CDCl(3) or C(6)D(6), whereas in DMSO-d(6) the corresponding monomers are at hand. Moreover, the NMR data of different related 1H-pyrazol-3-ol derivatives are presented. MDPI 2018-01-09 /pmc/articles/PMC6017633/ /pubmed/29315238 http://dx.doi.org/10.3390/molecules23010129 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Arbačiauskienė, Eglė
Krikštolaitytė, Sonata
Mitrulevičienė, Aiva
Bieliauskas, Aurimas
Martynaitis, Vytas
Bechmann, Matthias
Roller, Alexander
Šačkus, Algirdas
Holzer, Wolfgang
On the Tautomerism of N-Substituted Pyrazolones: 1,2-Dihydro-3H-pyrazol-3-ones versus 1H-Pyrazol-3-ols
title On the Tautomerism of N-Substituted Pyrazolones: 1,2-Dihydro-3H-pyrazol-3-ones versus 1H-Pyrazol-3-ols
title_full On the Tautomerism of N-Substituted Pyrazolones: 1,2-Dihydro-3H-pyrazol-3-ones versus 1H-Pyrazol-3-ols
title_fullStr On the Tautomerism of N-Substituted Pyrazolones: 1,2-Dihydro-3H-pyrazol-3-ones versus 1H-Pyrazol-3-ols
title_full_unstemmed On the Tautomerism of N-Substituted Pyrazolones: 1,2-Dihydro-3H-pyrazol-3-ones versus 1H-Pyrazol-3-ols
title_short On the Tautomerism of N-Substituted Pyrazolones: 1,2-Dihydro-3H-pyrazol-3-ones versus 1H-Pyrazol-3-ols
title_sort on the tautomerism of n-substituted pyrazolones: 1,2-dihydro-3h-pyrazol-3-ones versus 1h-pyrazol-3-ols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017633/
https://www.ncbi.nlm.nih.gov/pubmed/29315238
http://dx.doi.org/10.3390/molecules23010129
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