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

Johan Wouters, F. Javier Luque, Gloria Uccello Barretta, Federica Balzano, Rosario Pignatello, Salvatore Guccione

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)1012-1016
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number5
DOIs
Publication statusPublished - 1 Jan 2002
Externally publishedYes

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