Issue 3, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

The annular tautomerism of 4(5)-phenylimidazole

Rosa M. Claramunt,*a   María Dolores Santa María,a   Lourdes Infantes,b   Félix H. Canob  and  José Elgueroc  

* Corresponding authors

a Departamento de Química Orgánica y Biología, Facultad de Ciencias, UNED, Senda del Rey, 9, E-28040 Madrid, Spain
E-mail: rclaramunt@ccia.uned.es

b Departamento de Cristalografía, Instituto de Química-Física Rocasolano, CSIC, Serrano 119, E-28006 Madrid, Spain

c Instituto de Química Médica, Centro de Química Orgánica ‘Manuel Lora-Tamayo’, CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain

Abstract

A new polymorph of 4-phenylimidazole 1a has been characterised by X-ray crystallography. Both polymorphs present a secondary structure of chains, and the observed differences in the topology of their crystal packing are related to the conformational differences in the primary and secondary structural levels. NMR experiments (13C and 15N) reveal that tautomer 1a is the only one observed in the solid state, being also the most abundant in solution (80%) in agreement with high-level theoretical calculations which favour this tautomer over the 5-phenyl one. The results obtained for this compound are relevant for the structure of the related 4(5)-porphyrinylimidazole.

Graphical abstract: The annular tautomerism of 4(5)-phenylimidazole

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Article information

DOI
https://doi.org/10.1039/B109079H
Article type
Paper
Submitted
05 Oct 2001
Accepted
03 Dec 2001
First published
17 Jan 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 564-568

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The annular tautomerism of 4(5)-phenylimidazole

R. M. Claramunt, M. D. Santa María, L. Infantes, F. H. Cano and J. Elguero, J. Chem. Soc., Perkin Trans. 2, 2002, 564 DOI: 10.1039/B109079H

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