Issue 5, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Crystallographic, NMR and ab initio calculation studies of tautomerism among substituted dihydrothiazol-2-ylhydrazones

Johan Wouters,†a   F. Javier Luque,b   Gloria Uccello Barretta,c   Federica Balzano,c   Rosario Pignatellod  and  Salvatore Guccione*d  

* Corresponding authors

a Fac. Univ. ND de la Paix, 61 Rue de Bruxelles, Namur, Belgium
E-mail: johan.wouters@fundp.ac.be
Fax: 32 81 724530

b Departament de Fisicoquímica, Facultat de Farmàcia, Universitat de Barcelona, Av. Diagonal s/n, Barcelona, Spain
E-mail: javier@far1.far.ub.es
Fax: 34 93 4035987
Tel: 34 93 4024557

c Centro CNR di Studio per le Macromolecole Stereordinate ed Otticamente Attive, Dipartimento di Chimica e Chimica Industriale, Università degli Studi di Pisa, via Risorgimento 35, Pisa, Italy
E-mail: gloria@dcci.unip.it
Fax: +39 050 918260
Tel: +39 050 918250

d Dipartimento di Scienze Farmaceutiche, Facoltà di Farmacia, Università degli Studi di Catania, viale A. Doria 6, Ed. 2, Citta Universitaria, I-95125, Italy
E-mail: guccione@mbox.unict.it; pignatel@mbox.unict.it
Fax: +39 095 443604
Tel: +39 095 738-4020

Abstract

The structures of (±)-dihydrothiazolyl hydrazones 3a,b have been fully characterized by combining crystallography, NMR measurements in solution, and computational methods. The thiazolidine structure of the heterocycle is confirmed both by crystallography and in solution. The stability of the endocyclic N3 tautomeric form is confirmed by energy calculation at the MP2/6-31+G(d) level. The anti-E conformation observed in the crystal structures is retained in solution, in agreement with stability prediction.

Graphical abstract: Crystallographic, NMR and ab initio calculation studies of tautomerism among substituted dihydrothiazol-2-ylhydrazones

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Article information

DOI
https://doi.org/10.1039/B110321K
Article type
Paper
Submitted
12 Nov 2001
Accepted
28 Feb 2002
First published
22 Mar 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 1012-1016

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Crystallographic, NMR and ab initio calculation studies of tautomerism among substituted dihydrothiazol-2-ylhydrazones

J. Wouters, F. J. Luque, G. U. Barretta, F. Balzano, R. Pignatello and S. Guccione, J. Chem. Soc., Perkin Trans. 2, 2002, 1012 DOI: 10.1039/B110321K

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