Reaction of iminopropadienones with amines - Formation of zwitterionic intermediates, ketenes, and ketenimines

Naduvile Veedu, Rakesh, Kokas, Okanya J., Couturier-Tamburelli, Isabelle, Koch, Rainer, Aycard, Jean-Pierre, Borget, Fabien and Wentrup, Curt (2008) Reaction of iminopropadienones with amines - Formation of zwitterionic intermediates, ketenes, and ketenimines. Journal of Physical Chemistry A, 112 40: 9742-9750. doi:10.1021/jp803351q


Author Naduvile Veedu, Rakesh
Kokas, Okanya J.
Couturier-Tamburelli, Isabelle
Koch, Rainer
Aycard, Jean-Pierre
Borget, Fabien
Wentrup, Curt
Title Reaction of iminopropadienones with amines - Formation of zwitterionic intermediates, ketenes, and ketenimines
Journal name Journal of Physical Chemistry A   Check publisher's open access policy
ISSN 1089-5639
Publication date 2008-10-09
Year available 2008
Sub-type Article (original research)
DOI 10.1021/jp803351q
Open Access Status
Volume 112
Issue 40
Start page 9742
End page 9750
Total pages 8
Place of publication Washington, D.C. U.S.A.
Publisher American Chemical Society
Language eng
Subject 0399 Other Chemical Sciences
Abstract Five aryliminopropadienones 4a−d have been synthesized by flash vacuum thermolysis (FVT) by using two different precursors in each case. These compounds were deposited at 50 K at a pressure of ca. 10−6 mbar together with three different nucleophiles, namely, trimethylamine (TMA), dimethylamine (DMA), and diethylamine (DEA), in order to study their reactions as neat solids during warm-up by FTIR spectroscopy. The reaction with TMA showed that a zwitterionic species (5 and/or 6) was formed in all the cases. With DMA and DEA, an α-oxoketenimine and/or an imidoylketene (7 and 8 or 9 and 10) was formed as the final product. In addition, several bands were observed, which can be assigned to zwitterionic intermediates (11 or 12). Optimized structures and vibrational spectra for all products were calculated at the B3LYP/6-31G(d) level of theory by using the polarizable continuum model (ε = 5).
Keyword Density-functional Theory
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
School of Chemistry and Molecular Biosciences
 
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Created: Thu, 03 Sep 2009, 19:25:02 EST by Mr Andrew Martlew on behalf of Faculty of Science