Issue 12, 2010
From the journal:

CrystEngComm

Fast degenerate double proton transfer in the solid state between two indazolinone tautomers†‡

Marta Pérez-Torralba,*a   Concepción López,a   Carlos Pérez-Medina,a   Rosa M. Claramunt,*a   Elena Pinilla,b   M. Rosario Torres,b   Ibon Alkortac  and  José Elgueroc  

* Corresponding authors

a Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, Madrid, Spain
E-mail: mtaperez@ccia.uned.es
Fax: +34 913988372
Tel: +34 913988961

b Departamento de Química Inorgánica I, CAI de Difracción de Rayos-X, Facultad de Ciencias Químicas, Universidad Complutense de Madrid (UCM), Madrid, Spain

c Instituto de Química Médica (CSIC), Juan de la Cierva 3, Madrid, Spain

Abstract

The neutral dimer formed by 4,6-difluoro-1H,2H-indazolin-3-one and 3-hydroxy-4,6-difluoro-1H-indazole linked by two hydrogen bonds presents a very fast intermolecular double proton transfer in the solid state (ISSPT). The combined use of crystallography, solid state NMR and DFT [B3LYP/6-311++G(d,p)] calculations supports this interesting observation and allows us to estimate a barrier of about 20 kJ mol−1.

Graphical abstract: Fast degenerate double proton transfer in the solid state between two indazolinone tautomers

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Article information

DOI
https://doi.org/10.1039/C0CE00249F
Article type
Communication
Submitted
31 May 2010
Accepted
14 Aug 2010
First published
07 Sep 2010

CrystEngComm, 2010,12, 4052-4055

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Fast degenerate double proton transfer in the solid state between two indazolinone tautomers

M. Pérez-Torralba, C. López, C. Pérez-Medina, R. M. Claramunt, E. Pinilla, M. R. Torres, I. Alkorta and J. Elguero, CrystEngComm, 2010, 12, 4052 DOI: 10.1039/C0CE00249F

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