Issue 10, 2010
From the journal:

New Journal of Chemistry

Mechanisms of reactions conducted on α-amido-α-aminonitrones, determined based on the structures of their crystalline products and DFT calculations†

Bartosz Trzewik,*a   Tomasz Seidler,a   Ewa Brocławikb  and  Katarzyna Stadnickaa  

* Corresponding authors

a Faculty of Chemistry, Jagiellonian University, ul. Romana Ingardena 3, Poland
E-mail: trzewik@chemia.uj.edu.pl
Fax: +48 12 634 05 15
Tel: +48 12 663 22 97

b Institute of Catalysis and Surface Chemistry PAN, ul. Niezapominajek 8, Poland
E-mail: broclawi@chemia.uj.edu.pl
Tel: +48 12 663 20 23

Abstract

The crystal structures of several compounds obtained from recently synthesised α-amido-α-aminonitrones were determined by X-ray diffraction. The compounds belonged to three different classes: 1,2,5-oxadiazin-4-ones, amidines and dibenzo[d,f][1,3]diazepines. In spite of the fact that they were yielded in reactions of various kinds, all the products contained the same amido-amidine moiety. We discovered that some geometrical parameters within the moiety had non-typical values; for example the Csp2–Csp2 single bonds were outstandingly long. A detailed analysis of the products' geometry, aided by DFT calculations for selected structures, allowed us to propose mechanisms of their formation.

Graphical abstract: Mechanisms of reactions conducted on α-amido-α-aminonitrones, determined based on the structures of their crystalline products and DFT calculations

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Article information

DOI
https://doi.org/10.1039/C0NJ00193G
Article type
Paper
Submitted
12 Mar 2010
Accepted
04 May 2010
First published
11 Jun 2010

New J. Chem., 2010,34, 2220-2228

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Mechanisms of reactions conducted on α-amido-α-aminonitrones, determined based on the structures of their crystalline products and DFT calculations

B. Trzewik, T. Seidler, E. Brocławik and K. Stadnicka, New J. Chem., 2010, 34, 2220 DOI: 10.1039/C0NJ00193G

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