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Issue 6, 2007
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The structure of fluorinated indazoles: the effect of the replacement of a H by a F atom on the supramolecular structure of NH-indazoles

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Abstract

The structures of three NH-indazoles (3-methyl, 3-trifluoromethyl and 3-trifluoromethyl-4,5,6,7-tetrafluoroindazoles) have been determined by X-ray crystallography. These three compounds, together with 3-methyl-4,5,6,7-tetrafluoroindazole, whose X-ray structure could not be determined, have been studied using multinuclear magnetic resonance spectroscopy, including solid-state CPMAS. They all are 1H-tautomers. In the crystal, 3-methyl-1H-indazole forms hydrogen bonded dimers, whereas 3-trifluoromethyl-1H-indazole and 3-trifluoromethyl-4,5,6,7-tetrafluoro-1H-indazole crystallize as catemers. These catemers are chiral space group P32. They are the first examples of indazoles crystallizing in the form of helices of three-fold screw axis. Attempts at rationalizing this behavior on the basis of supramolecular interactions (hydrogen bonds and aromatic interactions) and GIAO calculations are discussed.

Graphical abstract: The structure of fluorinated indazoles: the effect of the replacement of a H by a F atom on the supramolecular structure of NH-indazoles

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Publication details

The article was received on 11 Dec 2006, accepted on 13 Mar 2007 and first published on 10 Apr 2007


Article type: Paper
DOI: 10.1039/B617988F
Citation: New J. Chem., 2007,31, 936-946
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    The structure of fluorinated indazoles: the effect of the replacement of a H by a F atom on the supramolecular structure of NH-indazoles

    J. Teichert, P. Oulié, K. Jacob, L. Vendier, M. Etienne, R. M. Claramunt, C. López, C. Pérez Medina, I. Alkorta and J. Elguero, New J. Chem., 2007, 31, 936
    DOI: 10.1039/B617988F

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