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- Title
The Quest for Carbenic Nitrile Imines: Experimental and Computational Characterization of C-Amino Nitrile Imine.
- Authors
Nunes, Cláudio M.; Reva, Igor; Rosado, Mário T. S.; Fausto, Rui
- Abstract
C-Amino nitrile imine has been generated as primary photoproduct (λ = 220 nm) of 5-amino-2H-tetrazole isolated in an argon matrix at 15 K. Subsequent photochemical experiments (λ = 330 nm) demonstrated that C-amino nitrile imine isomerizes to the corresponding three-membered-ring 1H-diazirine and decomposes to methylenimine. The experimentally observed vas(CNN) absorption at 1998 cm-1 and a carbenic resonance structure contribution of around 20%, predicted by natural resonance theory calculations, demonstrate that the protoproduced C-amino nitrile imine has significant carbenic character. These results pave the way to the discovery of carbenic nitrile imines.
- Subjects
NITRILIMINES; ORGANONITROGEN compounds; ORGANIC compounds; ORGANIC synthesis; ORGANIC chemistry
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 34, p7484
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201501153