Document Detail


Experimental and theoretical study of 2,6-difluorophenylnitrene, its radical cation, and their rearrangement products in argon matrices.
MedLine Citation:
PMID:  16680795     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
2,6-Difluorophenylnitrene was reinvestigated both experimentally, in Ar matrices at 10 K, and computationally, by DFT and CASSCF/CASPT2 calculations. Almost-pure samples of both neutral rearrangement products (the bicyclic azirine and the cyclic ketenimine) of a phenylnitrene were prepared and characterized for the first time. These samples were then subjected to X-irradiation in the presence of CH2Cl2 as an electron scavenger, which led to ionization of the neutral intermediates. Thereby, it was shown that only the phenylnitrene and the cyclic ketenimine yield stable radical cations, whereas the bicyclic azirine decays to both of these compounds on ionization. The cyclic ketenimine yields a novel aromatic azatropylium-type radical cation. The electronic structure of the title compound is discussed in detail, and its relation to those of the iso-pi-electronic benzyl radical and phenylcarbene is traced.
Authors:
Claudio Carra; Rafael Nussbaum; Thomas Bally
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemphyschem : a European journal of chemical physics and physical chemistry     Volume:  7     ISSN:  1439-4235     ISO Abbreviation:  Chemphyschem     Publication Date:  2006 Jun 
Date Detail:
Created Date:  2006-06-06     Completed Date:  2007-07-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100954211     Medline TA:  Chemphyschem     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  1268-75     Citation Subset:  -    
Affiliation:
Department of Chemistry, University of Fribourg, Ch. du Musée 9, 1700 Fribourg, Switzerland.
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