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

Eglė Arbačiauskienė; Sonata Krikštolaitytė; Aiva Mitrulevičienė; Aurimas Bieliauskas; Vytas Martynaitis; Matthias Bechmann; Alexander Roller; Algirdas Šačkus; Wolfgang Holzer

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

Eglė Arbačiauskienė
, Sonata Krikštolaitytė
, Aiva Mitrulevičienė
, Aurimas Bieliauskas
, Vytas Martynaitis
, Matthias Bechmann
, Alexander Roller
, Algirdas Šačkus
, Wolfgang Holzer

Institute of Organic Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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 (1H, 13C, 15N) 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 CDCl3 or C6D6, whereas in DMSO-d6 the corresponding monomers are at hand. Moreover, the NMR data of different related 1H-pyrazol-3-ol derivatives are presented.

Original language	English
Article number	129
Number of pages	15
Journal	Molecules
Volume	23
Issue number	1
Publication status	Published - Jan 2018

Fields of science

104 Chemistry
104021 Structural chemistry
104026 Spectroscopy
104015 Organic chemistry
104017 Physical chemistry
106002 Biochemistry
106041 Structural biology
301305 Medical chemistry

JKU Focus areas

Nano-, Bio- and Polymer-Systems: From Structure to Function
Engineering and Natural Sciences (in general)

Cite this

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

abstract = "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 (1H, 13C, 15N) 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 CDCl3 or C6D6, whereas in DMSO-d6 the corresponding monomers are at hand. Moreover, the NMR data of different related 1H-pyrazol-3-ol derivatives are presented.",

author = "Eglė Arba{\v c}iauskienė and Sonata Krik{\v s}tolaitytė and Aiva Mitrulevi{\v c}ienė and Aurimas Bieliauskas and Vytas Martynaitis and Matthias Bechmann and Alexander Roller and Algirdas {\v S}a{\v c}kus and Wolfgang Holzer",

year = "2018",

month = jan,

language = "English",

volume = "23",

journal = "Molecules",

issn = "1420-3049",

publisher = "MDPI",

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T1 - On the Tautomerism of N-Substituted Pyrazolones: 1,2-Dihydro-3H-pyrazol-3-ones versus 1H-Pyrazol-3-ols

AU - Arbačiauskienė, Eglė

AU - Krikštolaitytė, Sonata

AU - Mitrulevičienė, Aiva

AU - Bieliauskas, Aurimas

AU - Martynaitis, Vytas

AU - Bechmann, Matthias

AU - Roller, Alexander

AU - Šačkus, Algirdas

AU - Holzer, Wolfgang

PY - 2018/1

Y1 - 2018/1

N2 - 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 (1H, 13C, 15N) 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 CDCl3 or C6D6, whereas in DMSO-d6 the corresponding monomers are at hand. Moreover, the NMR data of different related 1H-pyrazol-3-ol derivatives are presented.

AB - 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 (1H, 13C, 15N) 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 CDCl3 or C6D6, whereas in DMSO-d6 the corresponding monomers are at hand. Moreover, the NMR data of different related 1H-pyrazol-3-ol derivatives are presented.

UR - https://www.scopus.com/pages/publications/85040518879

M3 - Article

SN - 1420-3049

VL - 23

JO - Molecules

JF - Molecules

IS - 1

M1 - 129

ER -

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

Abstract

Fields of science

JKU Focus areas

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Cite this