Issue 12, 2008
From the journal:

New Journal of Chemistry

A theoretical and experimental NMR study of the tautomerism of two phenylene-bis-C-substituted pyrazoles†

Dionisia Sanz,*a   Rosa M. Claramunt,a   Ibon Alkorta,b   José Elguero,b   Werner R. Thielc  and  Tobias Rüfferd  

* Corresponding authors

a Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, Madrid, Spain
E-mail: dsanz@ccia.uned.es

b Instituto de Química Médica, CSIC, Juan de la Cierva 3, Madrid, Spain
E-mail: ibon@iqm.csic.es

c Fachbereich Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Str. Geb. 54, Kaiserslautern, Germany
E-mail: thiel@chemie.uni-kl.de

d Institut für Chemie, Technische Universität Chemnitz, Chemnitz, Germany
E-mail: Tobias.rueffer@chemie.tu-chemnitz.de

Abstract

Two bis-pyrazolylbenzenes, one meta- and the other para-substituted, have been studied by multinuclear magnetic resonance both in solution and in the solid state, including 13C CP-MAS NMR variable temperature experiments. The tautomerism in DMSO-d6 solution has been studied and the most stable tautomers (the 3,3 and the 3,5) identified. In the solid state the meta derivative exists as the 3,3-tautomer while the tautomer of the para derivative is the 3,5 one. This latter tautomer exists in a dynamic equilibrium with the 5,3 one, representing a new and original example of proton transfer in the solid state (SSPT).

Graphical abstract: A theoretical and experimental NMR study of the tautomerism of two phenylene-bis-C-substituted pyrazoles

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Article information

DOI
https://doi.org/10.1039/B803855D
Article type
Paper
Submitted
05 Mar 2008
Accepted
18 Jun 2008
First published
03 Sep 2008

New J. Chem., 2008,32, 2225-2232

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A theoretical and experimental NMR study of the tautomerism of two phenylene-bis-C-substituted pyrazoles

D. Sanz, R. M. Claramunt, I. Alkorta, J. Elguero, W. R. Thiel and T. Rüffer, New J. Chem., 2008, 32, 2225 DOI: 10.1039/B803855D

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