Issue 18, 2003
From the journal:

Organic & Biomolecular Chemistry

An NMR and X-ray study of the structure of the azo coupling product of 4-dimethylaminopent-3-en-2-one and benzenediazonium-tetrafluoroborate

Petr Šimůnek,*a   Valerio Bertolasi,b   Antonín Lyčkac  and  Vladimír Macháčeka  

* Corresponding authors

a University of Pardubice, Department of Organic Chemistry, University of Pardubice, Nám. Čs. Legií 565, Pardubice, Czech Republic
E-mail: p.simunek@email.cz, vladimir.machacek@upce.cz.

b Università di Ferrara, Dipartimento di Chimica, Centro di Strutturistica Diffrattometrica, Via L. Borsari 46, Ferrara, Italy
E-mail: m38@dns.unife.it.

c Research Institute for Organic Syntheses, Pardubice-Rybitví, CZ-532 18, Czech Republic
E-mail: antonin.lycka@vuosas.cz.

Abstract

4-Dimethylaminopent-3-en-2-one reacts with two molecules of benzenediazonium-tetrafluoroborate to give compound 1. The structure of this compound was determined by means of X-ray analysis of its crystal and 1H, 13C and 15N NMR spectra of its solution in CDCl3. The molecule of this compound contains one azo group and one hydrazone group. The substance exists, both in crystal form and in solutions of concentrations above 0.1 mol l−1, in the form of a dimer, in which the pair of molecules are bound by two hydrogen bonds N–H⋯N. On diluting the solution, the dimers decompose, the two forms being in an equilibrium that is rapid on the NMR time scale.

Graphical abstract: An NMR and X-ray study of the structure of the azo coupling product of 4-dimethylaminopent-3-en-2-one and benzenediazonium-tetrafluoroborate

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Article information

DOI
https://doi.org/10.1039/B303206J
Article type
Paper
Submitted
20 Mar 2003
Accepted
30 Jul 2003
First published
15 Aug 2003

Org. Biomol. Chem., 2003,1, 3250-3256

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An NMR and X-ray study of the structure of the azo coupling product of 4-dimethylaminopent-3-en-2-one and benzenediazonium-tetrafluoroborate

P. Šimůnek, V. Bertolasi, A. Lyčka and V. Macháček, Org. Biomol. Chem., 2003, 1, 3250 DOI: 10.1039/B303206J

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