Tautomerism and hydrogen bonding in reaction products from 4-aminopent-3-en-2-one and diazonium ions

The azo-coupling products have been prepared from 4-aminopent-3-en-2-one and 4-chloro- or 4-nitrobenzenediazonium ion. Structure of the products obtained was studied by means of multinuclear NMR spectroscopy in CDCl 3 solutions and X-ray diffraction in solid state. Both products are predominantly pr...

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Bibliographic Details
Published inJournal of molecular structure Vol. 642; no. 1; pp. 41 - 51
Main Authors Šimůnek, Petr, Bertolasi, Valerio, Macháček, Vladimı́r
Format Journal Article
LanguageEnglish
Published Elsevier B.V 04.12.2002
Subjects
4-Aminopent-3-en-2-one
Diazonium ions
hydrogen bonding
Tautomerism
4-Aminopent-3-en-2-one
hydrogen bonding
Tautomerism
Diazonium ions
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Summary:The azo-coupling products have been prepared from 4-aminopent-3-en-2-one and 4-chloro- or 4-nitrobenzenediazonium ion. Structure of the products obtained was studied by means of multinuclear NMR spectroscopy in CDCl 3 solutions and X-ray diffraction in solid state. Both products are predominantly present as azo forms in both the solution and the solid state, the azo form content being higher in solid state. The substituent effect on azo-hydrazone tautomeric equilibrium of the substances is more significant in solution than in solid state.
ISSN:0022-2860
1872-8014
DOI:10.1016/S0022-2860(02)00271-5